CA2382751A1 - Inhibitors of factor xa - Google Patents
Inhibitors of factor xa Download PDFInfo
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- CA2382751A1 CA2382751A1 CA002382751A CA2382751A CA2382751A1 CA 2382751 A1 CA2382751 A1 CA 2382751A1 CA 002382751 A CA002382751 A CA 002382751A CA 2382751 A CA2382751 A CA 2382751A CA 2382751 A1 CA2382751 A1 CA 2382751A1
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- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
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- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
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Abstract
The present application relates to compounds of the general formula A-Y-D-E- G- J-K-L, wherein A, Y, D, E, G, J, K and L have the meanings given in the description, having activity against mammalian factor Xa. The compounds are useful in vitroor in vivofor preventing or treating coagulation disorders.
Description
INHIBITORS OF FACTOR Xa Related Annlications This application claims benefit of priority under 35 USC ~ 119(e) to U.S.
Provisional Application No. 60/135,819 filed on May 24, 1999, which is herein incorporated in its entirety by reference.
Field of the Invention This invention relates to novel compounds which are potent and highly selective inhibitors of isolated factor Xa or when assembled in the prothrombinase complex. These compounds show selectivity for factor Xa versus other proteases of the coagulation (e.g. thrombin, fVIIa, fIXa) or the fibrinolytic cascades (e.g.
plasminogen activators, plasmin). In another aspect, the present invention relates to novel monoamidino-containing compounds, their pharmaceutically acceptable salts, and pharmaceutically acceptable compositions thereof which are useful as potent and specific inhibitors of blood coagulation in mammals. In yet another aspect, the invention relates to methods for using these inhibitors as therapeutic agents for disease states in mammals characterized by coagulation disorders.
Background of the Invention Hemostasis, the control of bleeding, occurs by surgical means, or by the physiological properties of vasoconstriction and coagulation. This invention is particularly concerned with blood coagulation and ways in which it assists in maintaining the integrity of mammalian circulation after injury, inflammation, disease, congenital defect, dysfunction or other disruption. Although platelets and blood coagulation are both involved in thrombus formation, certain components of the coagulation cascade are primarily responsible for the amplification or acceleration of the processes involved in platelet aggregation and fibrin deposition.
Thrombin is a key enzyme in the coagulation cascade as well as in hemostasis. Thrombin plays a central role in thrombosis through its ability to catalyze the conversion of fibrinogen into fibrin and through its potent platelet activation activity. Direct or indirect inhibition of thrombin activity has been the focus of a variety of recent anticoagulant strategies as reviewed by Claeson, G., "Synthetic Peptides and Peptidomimetics as Substrates and Inhibitors of Thrombin and Other Proteases in the Blood Coagulation System", Blood Coag. Fibrinol.
5_, 411-436 (1994). Several classes of anticoagulants currently used in the clinic directly or indirectly affect thrombin (i.e. heparins, low-molecular weight heparins, heparin-like compounds and coumarins).
A prothrombinase complex, including Factor Xa (a serine protease, the activated form of its Factor X precursor and a member of the calcium ion binding, gamma carboxyglutamyl (Gla)-containing, vitamin K dependent, blood coagulation glycoprotein family), converts the zymogen prothrombin into the active procoagulant thrombin. Unlike thrombin, which acts on a variety of protein substrates as well as at a specific receptor, factor Xa appears to have a single physiologic substrate, namely prothrombin. Since one molecule of factor Xa may be able to generate up to 138 molecules of thrombin (Elodi et al., Thromb. Res. 1 S, 617-619 (1979)), direct inhibition of factor Xa as a way of indirectly inhibiting the formation of thrombin may be an efficient anticoagulant strategy. Therefore, it has been suggested that compounds which selectively inhibit factor Xa may be useful as in vitro diagnostic agents, or for therapeutic administration in certain thrombotic disorders, see e.g., WO 94/13693.
Polypeptides derived from hematophagous organisms have been reported which are highly potent and specific inhibitors of factor Xa. United States Patent 4,588,587 describes anticoagulant activity in the saliva of the Mexican leech, Haementeria o~cinalis. A principal component of this saliva was shown to be the polypeptide factor Xa inhibitor, antistasin (ATS), by Nutt, E. et al., "The Amino Acid Sequence of Antistasin, a Potent Inhibitor of Factor Xa Reveals a Repeated Internal Structure", J. Biol. Chem., ~, 10162-10167 (1988). Another potent and highly specific inhibitor of Factor Xa, called tick anticoagulant peptide (TAP), has been isolated from the whole body extract of the soft tick Ornithidoros moubata, as reported by Waxman, L., et al., "Tick Anticoagulant Peptide (TAP) is a Novel Inhibitor of Blood Coagulation Factor Xa" Science, 2,~8, 593-596 (1990).
Factor Xa inhibitory compounds which are not large polypeptide-type inhibitors have also been reported including: Tidwell, R.R. et al., "Strategies for Anticoagulation With Synthetic Protease Inhibitors. Xa Inhibitors Versus Thrombin Inhibitors", Thromb. Res., 1~, 339-349 (1980); Turner, A.D. et al., "p-Amidino Esters as Irreversible Inhibitors of Factor IXa and Xa and Thrombin", Biochemistry, 25, 4929-4935 (1986); Hitomi, Y. et al., "Inhibitory Effect of New Synthetic Protease Inhibitor (FUT-175) on the Coagulation System", Haemostasis, ~S, 164-168 (1985); Sturzebecher, J. et al., "Synthetic Inhibitors of Bovine Factor Xa and Thrombin. Comparison of Their Anticoagulant Efficiency", Thromb. Res., ~, 245-252 (1989); Kam, C.M. et al., "Mechanism Based Isocoumarin Inhibitors for Trypsin and Blood Coagulation Serine Proteases: New Anticoagulants", Biochemistry, ~, 2547-2557 (1988); Hauptmann, J. et al., "Comparison of the Anticoagulant and Antithrombotic Effects of Synthetic Thrombin and Factor Xa Inhibitors", Thromb. Haemost., ~~, 220-223 (1990); and the like.
Others have reported Factor Xa inhibitors which are small molecule organic compounds, such as nitrogen containing heterocyclic compounds which have amidino substituent groups, wherein two functional groups of the compounds can bind to Factor Xa at two of its active sites. For example, WO 98/28269 describes pyrazole compounds having a terminal C(=NH)-NHz group; WO 97/21437 describes benzimidazole compounds substituted by a basic radical which are connected to a naththyl group via a straight or branched chain alkylene,-C(=O) or -S(=O)2 bridging group; WO 99/10316 describes compounds having a 4-phenyl-N-alkylamidino-piperidine and 4-phenoxy-N-alkylamidino-piperidine group connected to a 3-amidinophenyl group via a carboxamidealkyleneamino bridge; and EP 798295 describes compounds having a 4-phenoxy-N-alkylamidino-piperidine group connected to an amidinonaphthyl group via a substituted or unsubstituted sulfonamide or carboxamide bridging group.
There exists a need for effective therapeutic agents for the regulation of hemostasis, and for the prevention and treatment of thrombus formation and other pathological processes in the vasculature induced by thrombin such as restenosis and inflammation. In particular, there continues to be a need for compounds which selectively inhibit factor Xa or its precursors. Compounds that have different combinations of bridging groups and functional groups than compounds previously discovered are needed, particularly compounds which selectively or preferentially bind to Factor Xa. Compounds with a higher degree of binding to Factor Xa than to thrombin are desired, especially those compounds having good bioavailability and/or solubility.
Summary! ,of the Invention The present invention relates to novel compounds which inhibit factor Xa, their pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives, and pharmaceutically acceptable compositions thereof which have particular biological properties and are useful as potent and specific inhibitors of blood coagulation in mammals. In another aspect, the invention relates to methods of using these inhibitors as diagnostic reagents or as therapeutic agents for disease states in mammals which have coagulation disorders, such as in the treatment or prevention of any thrombotically mediated acute coronary or cerebrovascular syndrome, any thrombotic syndrome occurring in the venous system, any coagulopathy, and any thrombotic complications associated with extracorporeal circulation or instrumentation, and for the inhibition of coagulation in biological samples.
In certain embodiments, this invention relates to novel compounds which are potent and highly selective inhibitors of isolated factor Xa when assembled in the prothrombinase complex. These compounds show selectivity for factor Xa versus other proteases of the coagulation cascade (e.g. thrombin, etc.) or the fibrinolytic cascade, and are useful as diagnostic reagents as well as antithrombotic agents.
In a preferred embodiment, the present invention provides a compound of the formula I:
A-Y-D-E-G-J-Z-L
wherein:
A is selected from:
(a) C,-C6 alkyl;
(b) C3-Cg-cycloalkyl;
(c) phenyl, which is independently substituted with 0-2 R' substituents;
(d) naphthyl, which is independently ' substituted with 0-2 R' substituents;and (e) a monocyclic or fused bicyclic heterocyclic ring system having from 5 to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R' substituents;
R' is selected from:
Halo, C,~,alkyl, Cz_6alkenyl, Cz_balkynyl, C3_8cycloalkyl, Co~alkylC3_ 8cycloalkyl,-CN, -NOz, (CHz)mNR2R3, SOzNRzR', SOZRz, CF3, ORz, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, C,-C4 alkyl, -CN C,~,alkyl, Cz_6alkenyl, Cz_ balkynyl, C3_$cycloalkyl, Co~alkylC3_gcycloalkyl and -NOz;
Rz and R3 are independently selected from the group consisting of H, C,~,alkyl, Cz_6alkenyl, Cz_6alkynyl, C3_gcycloalkyl, Co~alkylC3_8cycloalkyl, Co~alkylphenyl and Co~alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C,~alkyl, Cz_6alkenyl, Cz_6alkynyl, C3_$cycloalkyl, Co~alkylC3_gcycloalkyl, -CN, and -NOz 1 S m is an integer of 0-2;
Y is a member selected from the group consisting of a direct link, -C(=O)-, -N(R4)-, -C(=O)-N(R4)-, -N(R4)-C(=O)-, -SOz-, -O-, -SOz-N(R4)- and N(R4)-SOz-;
R4 is selected from:
H, C,~alkyl, Cz_6alkenyl, Cz_balkynyl, C3_8cycloalkyl, C~alkylC3_8cycloalkyl, Co~alkylphenyl and C~alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C,~alkyl, Cz_6alkenyl, Cz_6alkynyl, C3_8cycloalkyl, Co~alkylC3_8cycloalkyl, -CN, and -NOz;.
D is a direct link or is a member selected from the group consisting of (a) phenyl, which is independently substituted with 0-2 R'a substituents;
(b) naphthyl, which is independently substituted with 0-2 R'a substituents; and (c) a monocyclic or fused bicyclic heterocyclic ring system having from to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R'a substituents;
S R'a is selected from:
Halo, C,.~alkyl, Cz_6alkenyl, Cz_balkynyl, C3_8cycloalkyl, Co~alkylC3_ 8cycloalkyl, -CN, -NOz, (CHz)mNRzeR'a, SOZNRzaR38, SOZRza, CF3, ORza, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, C,~alkyl, Cz_6alkenyl, Cz_ 6alkynyl, C3_$cycloalkyl, C~alkylC3_$cycloalkyl, -CN and -NOz;
Rze and R3a are independently selected from the group consisting of H, C,~alkyl, Cz_6alkenyl, Cz_6alkynyl, C3_gcycloalkyl, Co~alkylC3_8cycloalkyl, Co~alkylphenyl and C~alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C,~alkyl, Cz_6alkenyl, Cz_6alkynyl, C3_gcycloalkyl, Co~alkylC3_8cycloalkyl, -CN and _NOz ~.
E is a member selected from the group consisting of:
-N(RS)-C(=O)-, -C(=O)-N(RS)-, -N(RS)-C(=O)-N(R6)-, -SOz N(RS)-, -N(RS)-SOz-N(R6)- and -N(RS)-SOz N(R6)-C(=O)-;
RS and R6 are independently selected from:
H, C,~alkyl, Cz_6alkenyl, Cz_6alkynyl, C3_8cycloalkyl, C~alkylC3_$cycloalkyl, Co~alkylphenyl, Co~alkylnaphthyl, C~alkylheteroaryl, C,,~alkylCOOH and C,~alkylCOOC,~alkyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl, naphthyl and heteroaryl moieties may be independently replaced with a member selected from the group consisting of halo, C,~alkyl, Cz_6alkenyl, Cz_6alkynyl, C3_8cycloalkyl, Co~alkylC3_$cycloalkyl, -CN and -NOz;
G is selected from:
_7_ -CR'R$- and -CR'Rga-CR'~RBb-wherein R', Rg, R'a, RBa, R'~ and R8b are independently a member selected from from the group consisting of:
hydrogen, C,~alkyl, Cz_6alkenyl, CZ_6alkynyl, C3_8cycloalkyl, C~alkyl-C3_ S gcycloalkyl, C°~,alkylphenyl, C°~alkylnaphthyl, -OR9,-C°~alkylCOOR9, -C°~alkylC(=O)NR9R'°, -C°.~alkylC(=O)NR9-CHZ-CHZ O-R'°, -Co~alkylC(=O)NR9(-CHZ-CHZ-O-R'°-)2, -N(R9)COR'°, -N(R9)C(=O)R'°, -N(R9)SOZR'°, and a naturally occurring or synthetic amino acid side chain, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C,~alkyl, CZ_6alkenyl, Cz_balkynyl, C3_ 8cycloalkyl, C°~alkyl-C3_8cycloalkyl, -CN and -NO2;
R9 and R'° are independently selected from:
H, C,~alkyl, C°~alkylphenyl and C°~alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C,~alkyl, CZ_6alkenyl, Cz_6alkynyl, C3_$cycloalkyl, C°~alkyl-C3_ 8cycloalkyl, -CN and -NO2, and wherein R9 and R'° taken together can form a 5-8 membered heterocylic ring;
J is a member selected from the group consisting of:
a direct link, -CH(R")- and -CH(R")-CHz ;
R' ' is a member selected from the group consisting of hydrogen, C,~alkyl, CZ_6alkenyl, Cz_6alkynyl, C3_gcycloalkyl, C°~alkyl-C3_ 8cycloalkyl, C°~alkylphenyl, C~alkylnaphthyl, C°-0alkylheterocyclic ring having from 1 to 4 hetero ring atoms selected from the group consisting of N, O and S, CHZCOOC,~alkyl, CHZCOOC,~,alkylphenyl and CHZCOOC,~alkylnaphthyl;
Z is a member selected from the group consisting of:
(a) phenyl, which is independently substituted with 0-2 R'b substituents;
_g_ (b) naphthyl, which is independently substituted with 0-2 R'b substituents; and (c) a monocyclic or fused bicyclic heterocyclic ring system having from S to 10 ring atoms, wherein 1-4 ring atoms of the ring system are S selected from N, O and S, and wherein the ring system may be substituted with 0-2 R'b substituents;
R'b is selected from:
Halo, C,~alkyl, Cz_6alkenyl, Cz_6alkynyl, C,_gcycloalkyl, Co~alkylC3_ $cycloalkyl, -CN, -NOz, NRzbR3b~ SOZNRzbR3b, SOzRzb, CF3, ORzb, O-CHZ
CHz-ORzb, O-CHz-COORzb, N(Rzb)-CHZ CHz ORzb, N(-CHz-CHz ORzb)z, N(Rzb)-C(=O)R3b, N(Rzb)-SOz-R'b, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, C,~alkyl, Cz_balkenyl, Cz_6alkynyl, C3_8cycloalkyl, C~alkylC3_ gcycloalkyl, -CN and -NOz;
Rzb and R3b are independently selected from the group consisting of H, C,~alkyl, Cz_6alkenyl, Cz_6alkynyl, C3_gcycloalkyl, Co~alkylC3_acycloalkyl, _ C~alkylphenyl and Co~alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C,~alkyl, Cz_6alkenyl, Cz_balkynyl, C3_acycloalkyl, Co~alkylC3_gcycloalkyl, -CN and -NOz L is selected from:
$~ _CN~ C(-O)yzR~s~ (Cgz)nWzRi3~ ~(-~12)~12R13' ~12R13' OR'z, -~12~(-~12)~12R13' and NRIZC(=NR'z)-R'3;
R'z and R'3 are independently selected from:
hydrogen, -OR'4, -NR'4R'S, C,~alkyl, Co~alkylphenyl, Co~alkylnaphthyl, COOC,~,alkyl, COO-Co~alkylphenyl and COO-Co~alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C,~alkyl, CZ_6alkenyl, CZ_6alkynyl, C3_8cycloalkyl, Co~alkylC3_gcycloalkyl, -CN, and -NO2;
R'4 and R'S are independently selected from:
H, C,~alkyl, Cz_6alkenyl, CZ_6alkynyl, C3_$cycloallcyl, Co~alkylC3_8cycloalkyl, C~,,alkylphenyl and Co~alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C,~alkyl, Cz_6alkenyl, CZ_6alkynyl, C3_gcycloalkyl, Co~alkylC3_8cycloalkyl, -CN, and -NOZ;
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
In certain aspects of this invention, compounds are provided which are useful as diagnostic reagents. In another aspect, the present invention includes pharmaceutical compositions comprising a pharmaceutically effective amount of the 1 S compounds of this invention and a pharmaceutically acceptable Garner. In yet another aspect, the present invention includes methods comprising using the above compounds and pharmaceutical compositions for preventing or treating disease states characterized by undesired thrombosis or disorders of the blood coagulation process in mammals, or for preventing coagulation in biological samples such as, for example, stored blood products and samples. Optionally, the methods of this invention comprise administering the pharmaceutical composition in combination with an additional therapeutic agent such as an antithrombotic and/or a thrombolytic agent and/or an anticoagulant.
The preferred compounds also include their pharmaceutically acceptable isomers, hydrates, solvates, salts and prodrug derivatives.
Detailed Description of the Invention Definitions In accordance with the present invention and as used herein, the following terms are defined with the following meanings, unless explicitly stated otherwise.
The term "alkenyl" refers to a trivalent straight chain or branched chain unsaturated aliphatic radical. The term "alkinyl" (or "alkynyl") refers to a straight or branched chain aliphatic radical that includes at least two carbons joined by a triple bond. If no number of carbons is specified alkenyl and alkinyl each refer to radicals having from 2-12 carbon atoms.
The term "alkyl" refers to saturated aliphatic groups including straight-chain, branched-chain and cyclic groups having the number of carbon atoms specified, or if no number is specified, having up to 12 carbon atoms. The term "cycloalkyl" as used herein refers to a mono-, bi-, or tricyclic aliphatic ring having 3 to 14 carbon atoms and preferably 3 to 7 carbon atoms.
As used herein, the terms "carbocyclic ring structure " and " C3_,6 carbocyclic mono, bicyclic or tricyclic ring structure" or the like are each intended to mean stable ring structures having only carbon atoms as ring atoms wherein the ring structure is a substituted or unsubstituted member selected from the group consisting of: a stable monocyclic ring which is aromatic ring ("aryl") having six ring atoms; a stable monocyclic non-aromatic ring having from 3 to 7 ring atoms in the ring;
a stable bicyclic ring structure having a total of from 7 to 12 ring atoms in the two rings wherein the bicyclic ring structure is selected from the group consisting of ring structures in which both of the rings are aromatic, ring structures in which one of the rings is aromatic and ring structures in which both of the rings are non-aromatic; and a stable tricyclic ring structure having a total of from 10 to 16 atoms in the three rings wherein the tricyclic ring structure is selected from the group consisting of ring structures in which three of the rings are aromatic, ring structures in which two of the rings are aromatic and ring structures in which three of the rings are non-aromatic. In each case, the non-aromatic rings when present in the monocyclic, bicyclic or tricyclic ring structure may independently be saturated, partially saturated or fully saturated. Examples of such carbocyclic ring structures include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, cyclooctyl, [3.3.0]bicyclooctane, [4.3.0]bicyclononane, [4.4.0]bicyclodecane (decalin), 2.2.2]bicyclooctane, fluorenyl, phenyl, naphthyl, indanyl, adamantyl, or tetrahydronaphthyl (tetralin). Moreover, the ring structures described herein may be attached to one or more indicated pendant groups via any carbon atom which results in a stable structure. The term "substituted" as used in conjunction with carbocyclic ring structures means that hydrogen atoms attached to the ring carbon atoms of ring structures described herein may be substituted by one or more of the substituents indicated for that structure if such substitutions) would result in a stable compound.
The term "aryl" which is included with the term "carbocyclic ring structure"
refers to an unsubstituted or substituted aromatic ring, substituted with one, two or three substituents selected from loweralkoxy, loweralkyl, loweralkylamino, hydroxy, halogen, cyano, hydroxyl, mercapto, vitro, thioalkoxy, carboxaldehyde, carboxyl, carboalkoxy and carboxamide, including but not limited to carbocyclic aryl, heterocyclic aryl, and biaryl groups and the like, all of which may be optionally substituted. Preferred aryl groups include phenyl, halophenyl, loweralkylphenyl, napthyl, biphenyl, phenanthrenyl and naphthacenyl.
The term "arylalkyl" which is included with the term "carbocyclic aryl"
refers to one, two, or three aryl groups having the number of carbon atoms designated, appended to an alkyl group having the number of carbon atoms designated. Suitable arylalkyl groups include, but are not limited to, benzyl, picolyl, 1 S naphthylmethyl, phenethyl, benzyhydryl, trityl, and the like, all of which may be optionally substituted.
As used herein, the term "heterocyclic ring" or "heterocyclic ring system" is intended to mean a substituted or unsubstituted member selected from the group consisting of stable monocyclic ring having from 5-7 members in the ring itself and having from 1 to 4 hetero ring atoms selected from the group consisting of N, O and S; a stable bicyclic ring structure having a total of from 7 to 12 atoms in the two rings wherein at least one of the two rings has from 1 to 4 hetero atoms selected from N, O and S, including bicyclic ring structures wherein any of the described stable monocyclic heterocyclic rings is fused to a hexane or benzene ring; and a stable tricyclic heterocyclic ring structure having a total of from 10 to 16 atoms in the three rings wherein at least one of the three rings has from 1 to 4 hetero atoms selected from the group consisting of N, O and S. Any nitrogen and sulfur atoms present in a heterocyclic ring of such a heterocyclic ring structure may be oxidized.
Unless indicated otherwise the terms "heterocyclic ring" or "heterocyclic ring system" include aromatic rings, as well as non-aromatic rings which can be saturated, partially saturated or fully saturated non-aromatic rings. Also, unless indicated otherwise the term "heterocyclic ring system" includes ring structures wherein all of the rings contain at least one hetero atom as well as structures having less than all of the rings in the ring structure containing at least one hetero atom, for example bicyclic ring structures wherein one ring is a benzene ring and one of the rings has one or more hetero atoms are included within the term "heterocyclic ring systems" as well as bicyclic ring structures wherein each of the two rings has at least one hetero atom. Moreover, the ring structures described herein may be attached to one or more indicated pendant groups via any hetero atom or carbon atom which results in a stable structure. Further, the term "substituted" means that one or more of the hydrogen atoms on the ring carbon atoms) or nitrogen atoms) of the each of the rings in the ring structures described herein may be replaced by one or more of the indicated substituents if such replacements) would result in a stable compound.
Nitrogen atoms in a ring structure may be quaternized, but such compounds are specifically indicated or are included within the term "a pharmaceutically acceptable salt" for a particular compound. When the total number of O and S atoms in a single heterocyclic ring is greater than 1, it is preferred that such atoms not be adjacent to one another. Preferably, there are no more that 1 O or S ring atoms in the same ring of a given heterocyclic ring structure.
Examples of monocylic and bicyclic heterocylic ring systems, in alphabetical order, are acridinyl, azocinyl, benzimidazolyl, benzofuranyl, benzothiofuranyl, benzothiophenyl, benzoxazolyl, benzthiazolyl, benztriazolyl, benztetrazolyl, benzisoxazolyl, benzisothiazolyl, benzimidazalinyl, carbazolyl, 4aH-carbazolyl, carbolinyl, chromanyl, chromenyl, cinnolinyl, decahydroquinolinyl, 2H,6H-1,5,2-dithiazinyl, dihydrofuro[2,3-b]tetrahydrofurarl, furanyl, furazanyl, imidazolidinyl, imidazolinyl, imidazolyl, 1H-indazolyl, indolinyl, indolizinyl, indolyl, 3H-indolyl, isobenzofuranyl, isochromanyl, isoindazolyl, isoindolinyl, isoindolyl, isoquinolinyl (benzimidazolyl), isothiazolyl, isoxazolyl, morpholinyl, naphthyridinyl, octahydroisoquinolinyl, oxadiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, oxazolidinyl, oxazolyl, oxazolidinyl, pyrimidinyl, phenanthridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxathiinyl, phenoxazinyl, phthalazinyl, piperazinyl, piperidinyl, pteridinyl, purinyl, pyranyl, pyrazinyl, pyroazolidinyl, pyrazolinyl, pyrazolyl, pyridazinyl, pryidooxazole, pyridoimidazole, pyridothiazole, pyridinyl, pyridyl, pyrimidinyl, pyrrolidinyl, pyrrolinyl, 2H-pyrrolyl, pyrrolyl, quinazolinyl, quinolinyl, 4H-quinolizinyl, quinoxalinyl, quinuclidinyl, tetrahydrofuranyl, tetrahydroisoquinolinyl, tetrahydroquinolinyl, 6H-1,2,5-thiadazinyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, thianthrenyl, thiazolyl, thienyl, thienothiazolyl, thienooxazolyl, thienoimidazolyl, thiophenyl, triazinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,2,5-triazolyl, 1,3,4-triazolyl and xanthenyl. Preferred heterocyclic ring structures include, but are not limited to, pyridinyl, furanyl, thienyl, pyrrolyl, pyrazolyl, pyrrolidinyl, imidazolyl, indolyl, benzimidazolyl, 1H-indazolyl, oxazolinyl, or isatinoyl. Also included are fused ring and spiro compounds containing, for example, the above heterocylic ring structures.
As used herein the term "aromatic heterocyclic ring system" has essentially the same definition as for the monocyclic and bicyclic ring systems except that at least one ring of the ring system is an aromatic heterocyclic ring or the bicyclic ring has an aromatic or non-aromatic heterocyclic ring fused to an aromatic carbocyclic ring structure.
The terms "halo" or "halogen" as used herein refer to Cl, Br, F or I
substituents. The term "haloalkyl", and the like, refer to an aliphatic carbon radicals having at least one hydrogen atom replaced by a Cl, Br, F or I atom, including mixtures of different halo atoms. Trihaloalkyl includes trifluoromethyl and the like as preferred radicals, for example.
The term "methylene" refers to -CH2-.
The term "pharmaceutically acceptable salts" includes salts of compounds derived from the combination of a compound and an organic or inorganic acid.
These compounds are useful in both free base and salt form. In practice, the use of the salt form amounts to use of the base form; both acid and base addition salts are within the scope of the present invention.
"Pharmaceutically acceptable acid addition salt" refers to salts retaining the biological effectiveness and properties of the free bases and which are not biologically or otherwise undesirable, formed with inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid and the like, and organic acids such as acetic acid, propionic acid, glycolic acid, pyruvic acid, oxalic acid, malefic acid, malonic acid, succinic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, p-toluenesulfonic acid, salicyclic acid and the like.
"Pharmaceutically acceptable base addition salts" include those derived from inorganic bases such as sodium, potassium, lithium, ammonium, calcium, magnesium, iron, zinc, copper, manganese, aluminum salts and the like.
Particularly preferred are the ammonium, potassium, sodium, calcium and magnesium salts.
Salts derived from pharmaceutically acceptable organic nontoxic bases include salts of primary, secondary, and tertiary amines, substituted amines including naturally occurring substituted amines, cyclic amines and basic ion exchange resins, such as isopropylamine, trimethylamine, diethylamine, triethylamine, tripropylamine, ethanolamine, 2-diethylaminoethanol, trimethamine, dicyclohexylamine, lysine, arginine, histidine, caffeine, procaine, hydrabamine, choline, betaine, ethylenediamine, glucosamine, methylglucamine, theobromine, purines, piperizine, piperidine, N-ethylpiperidine, polyamine resins and the like. Particularly preferred organic nontoxic bases are isopropylamine, diethylamine, ethanolamine, trimethamine, dicyclohexylamine, choline, and caffeine.
"Biological property" for the purposes herein means an in vivo effector or antigenic function or activity that is directly or indirectly performed by a compound of this invention that are often shown by in vitro assays. Effector functions include receptor or ligand binding, any enzyme activity or enzyme modulatory activity, any Garner binding activity, any hormonal activity, any activity in promoting or inhibiting adhesion of cells to an extracellular matrix or cell surface molecules, or any structural role. Antigenic functions include possession of an epitope or antigenic site that is capable of reacting with antibodies raised against it.
In the compounds of this invention, carbon atoms bonded to four non-identical substituents are asymmetric. Accordingly, the compounds may exist as diastereoisomers, enantiomers or mixtures thereof. The syntheses described herein may employ racemates, enantiomers or diastereomers as starting materials or intermediates. Diastereomeric products resulting from such syntheses may be separated by chromatographic or crystallization methods, or by other methods known in the art. Likewise, enantiomeric product mixtures may be separated using the same techniques or by other methods known in the art. Each of the asymmetric carbon atoms, when present in the compounds of this invention, may be in one of two configurations (R or S) and both are within the scope of the present invention.
Preferred Embodiments In a preferred embodiment, the present invention provides a compound according to the formula I:
A-Y-D-E-G-J-Z-L
wherein:
A is selected from:
(a) C,-C6 alkyl;
(b) C3-C$ cycloalkyl;
(c) phenyl, which is independently substituted with 0-2 R' substituents;
(d) naphthyl, which is independently substituted with 0-2 R' substituents;
and (e) a monocyclic or fused bicyclic heterocyclic ring system having from 5 to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R' substituents;
R' is selected from:
halo, C,~alkyl, -CN, (CHZ)mNR2R3, SOzNR2R3, SOZRz, CF3, ORz, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S;
Rz and R' are independently selected from the group consisting of:
H, C,~alkyl and Co~alkylaryl, m is an integer of 0-2;
Y is a member selected from the group consisting of a direct link, -C(=O)-, -N(R4)-, -C(=O)-N(R')-, -N(R°)-C(=O)-, -SOZ-, -O-, -SOZ-N(R4)- and -N -SOZ i R4 is selected from:
H, C,_4alkyl and Co~alkylaryl;.
D is absent or is a member selected from the group consisting of (a) aryl, which is independently substituted with 0-2 R'a substituents; and (b) a monocyclic or fused bicyclic heterocyclic ring system having from S to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R'a substituents;
S R'a is selected from:
Halo, C,~alkyl, -CN, -NO2, (CHz)mNR2aR'a, SOzNR2aR38, SOzRza, CF3, ORZa, and a 5-6 membered aromatic heterocyclic ring containing from 1-4 heteroatoms selected from N, O and S;
RZa and R38 are independently selected from the group consisting of H, C,~alkyl and Co.,,alkylaryl;
E is a member selected from the group consisting of -N(R5)_C(=O)_, -C(=O)_N(Rs)_, -N(R5)_C(=O)_N(R6)_, -SOz_N(R5)_, -N(RS)-SOZ-N(R6)- and N(RS)-SOZ N(R6)-C(=O)-;
RS and R6 are independently selected from:
H, C,~alkyl, C~,alkylaryl, C°~alkylheteroaryl, C,.~alkylCOOH and C,~alkylCOOC,~alkyl;
G is selected from:
-CR'R8- and -CR'R$a-CR'~Rgb-wherein R', Rg, R'a, R88, R'~ and R$b are independently a member selected from from the group consisting of hydrogen, C,_4alkyl, Co.~alkyl-C3_gcycloalkyl, Co~alkylaryl, -OR9, -C~alkylCOOR9, -Co.~alkylC(=O)NR9R'°, -N(R9)COR'°, -N(R9)C(=O)R'°, -N(R9)SOZR'°, and common amino acid side chains;
R9 and R'° are independently selected from:
H, C,~alkyl and C°~alkylaryl;
J is a member selected from the group consisting of a direct link, -CH(R")- and -CH(R")-CHZ-;
R" is a member selected from the group consisting of:
hydrogen, C,~alkyl, Cz_6alkenyl, Cz_6alkynyl, C,_gcycloalkyl, C~alkylaryl, C~alkylheterocyclics, CHzCOOC,~alkyl, CHZCOOC,~alkylaryl;
Z is a member selected from the group consisting of (a) aryl, which is independently substituted with 0-2 R'b substituents;and S (b) a monocyclic or fused bicyclic heterocyclic ring system having from to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R'b substituents;
R'b is selected from:
halo, C,~alkyl, -CN, -NOz, NRzbR36~ SOZNRzbR3b~ SOZRzb, CF3, ORzb, O-CHz-CHz ORzb, O-CHZ COORzb, N(Rzb)-CHz-CHz-ORzb, N(-CHz-CHZ ORzb)z, N(Rzb)-C(=O)R3b, N(Rzb)-SOz-R3b, and a 5-6 membered aromatic heterocyclic ring containing from 1-4 heteroatoms selected from N, O and S;
Rzb and R3b are independently selected from the group consisting of H, C,~alkyl and Co~alkylaryl;
L is selected from:
H~ -CN~ C(-O)~12R13' (CHz)~WzR~s~ C(_~12)NR.'zRl3~ yzRi3, OR'z, -~12C(-~12)~12R13 ~d NR'zC(=NR'2)-R13;
R'z and R'3 are independently selected from:
hydrogen, -OR'°, -NR'4R's, C,~alkyl, Co~alkylaryl COOC,~alkyl, and COO-Co~alkylaryl;
R'4 and R's are independently selected from:
H and C,~alkyl; and and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
In a further preferred embodiment, the present invention provides a compound according to the formula I:
A-Y-D-E-G-J-Z-L
wherein:
A is selected from:
(a) phenyl, which is independently substituted with 0-2 R' substituents;
and (b) a monocyclic or fused bicyclic heterocyclic ring system having from S to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R' substituents;
R' is selected from:
halo, (CHZ)mNRzR', SOzNRzR3 and SOZRZ;
RZ and R3 are independently selected from the group consisting of H and C,_4alkyl;
Y is a member selected from the group consisting of a direct link, -C(=O)-, - SOz- and -O-;
D is a member selected from the group consisting of:
(a) phenyl, which is independently substituted with 0-2 R'a substituents;
and (b) a monocyclic or fused bicyclic heterocyclic ring system having from 5 to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R'a substituents;
R'a is selected from:
Halo and C,~,alkyl;
RZa and R3a are independently selected from the group consisting of H, C,~alkyl, Co~alkylaryl;
E is a member selected from the group consisting of:
-N(RS)-C(=O)- and -C(=O)-N(RS)-;
RS and R6 are independently selected from:
H, C,~alkyl, C°~alkylaryl and C°~alkylheteroaryl;
G is selected from:
-CR'Rg- arid -CR'Rga-CR'~RBb-wherein R', R8, R'a, Rga, R'~ and R$b are independently a member selected from from the group consisting of hydrogen, C,~alkyl, C~alkyl-C3_gcycloalkyl, C°~alkylaryl, -OR9, -C°~alkylCOOR9, -C°_4alkylC(=O) NR9R'°, -C°~alkylC(=O)NR9-CHz-CHz-O-R'°, -Co_aalkylC(=O)NR9(-CHz-CHz-O-R'o-)z, -N(R9)COR'°, -N(R9)C(=O)R'°, -N(R9)SOZR'°, and common amino acid side chains;
R9 and R'° are independently selected from:
H and C,~alkyl, wherein the NR9R'° group of R', Rg, R'a, RBa, R'~ and R8b is optionally cyclized to form a 5-8 membered heterocyclic group;
J is a member selected from the group consisting of a direct link, -CH(R")- and -CH(R")-CHz-;
R" is a member selected from the group consisting of:
hydrogen, C,~alkyl, Cz_6alkenyl, C°~allcylaryl and a C°~alkylheterocyclic ring;
Z is a member selected from the group consisting of (a) phenyl, which is independently substituted with 0-2 R'b substituents;
(b) an aromatic heterocyclic ring having , from 5 to 10 ring atoms, wherein 1-4 ring atoms are selected from N, O and S, and wherein the ring may be subsituted independently by from 0-2 R'b substituents;
and (c) a fused aromatic bicyclic heterocyclic ring system having from 5 to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, wherein the bicyclic ring system may be substituted with 0-2 R'b substituents;
R'b is selected from:
halo, C,~alkyl, OH, OBn, O-CHz-CHz-OH, O-CHz-CHz-OCH3, S O-CHZ-COOH, O-CHz-C(=O)-O-CH3, NHZ, NH-CHz CHZ O-CH3, NH-C(=O)-O-CH3, and NH-SOZ CH3;
L is selected from:
H~ C(-O)yzRts~ (CHz)nWzRts ~d C(=NR'z)NR'zRta;
R'z and R" are independently selected from:
hydrogen and C,~alkyl;
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
In a further preferred embodiment, the present invention provides a compound according to formula I:
A-D-E-G-J-Z-L
wherein A is a member selected from the group consisting of OZNHZ OZNHMe OzNHBu(t) OZMe HZNHZ HzNMeZ
D is a member selected from the group consisting of / \ /- / \ / \
F
F F F
/ \ / \ / \
F a F
E is a member selected from the group consisting of::
-C(=O)-NH-, -C(=O)-N(-CH3)-, C(=O)-N(-Bn)-, -NH-C(=O)-, -N(-CH3)-C(=O)- and -N(-Bn)C(=O)-;
G is selected from:
-CH-(-NHz)-CHZ-, -CH-(-NH(C(=O)-CH3))-CHZ-, -CH-(-NH(C(=O)-Ph))-CHz , -CH-(C(=O)-OR$)-, -CH(-R')-, -CHZ CH(C(=O)-OR$)-, and -CHZ-CH(C(=O)-N(-R8, -R$))-;
R' is a member selected from the group consisting of H, phenyl, Bn, -O-loweralkyl and cyclohexyl;
R8 is a member selected from the group consisting of H, C,_6alkyl, -O-loweralkyl and C3_6cycloalkyl;
J is a member selected from the group consisting of;
a direct link, -CH(R")- and -CH(R")-CHz ;
R" is a member selected from the group consisting of H, methyl, phenyl and benzyl; and Z and L taken together are a member selected from the group consisting of:
OCHzCOOH OH F OMe OCHZCHzOH OCHzCHZOMe \ \
I/ I/ I/ I/ I/ I/ I/
HzN NH H2 NH Hz NH Hz NH Hz NH Hz NH Hz NH
OCHZCOOMe NHCHzCOOH N(CI-llCHzOMe~ NH(CHZCCHzOMe) I\ I\ I\ I\ I/_ I/
/ F ~OH
/ / /
Hz NH Hz NH
Hz NH HzN NH Hz NH HzN NH
\ \ \
\ \ \ I I I I
I
/ I / \ / NH / O / S /
Nhz I ~ -N -N -N
Hz O HzN HzN HZN HzN Hz NH
OH NHz OH NHz \ \
\ \
/ I \ I / I / I / S I / NH
\ ~NH ~O
N~ I / N N ~NHz ~NH2 H2N O N~ HyN HyN
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
The following non-limiting tables illustrate representative compounds of the present invention:
Table 1 R~ Rtn, Rib H H H
Me H OH
I \ F H
-OH F
OH
Br OH
Hy-O
OCH2Ph F
CHyCH ~O~
O
~ OCH2CH20Me H
CHZCHZ"NHMe O
JI~I H H
CHZCHZ"NMe2 O
H H
CHZCH ~N
Formula II
Table 1 a 1b"
R7 Rlb H H H
Me H OH
F H
/ -OH F
Hz OH
/ Br OH
Hz Me Hz OCHZCHZOMe / OCH 2Ph F
CHz CHzCOOH
OCH2CH20Me H
Hz HN
H , H
Hz N H H
CHz Formula II
Table 2 R7 Rtb H H
MB H
\ F
-OH
OH
Bf \ -NH2 ~ ~ OCH 2Ph CHZCHZ"O' O
OCH2CH20Me CHZCH ~NHMe ~ H
CHZCHZ' _NMez H
CHZCH ~N
Formula III
Table 2a m H H
Me H
F
I\
/ -OH
CHz OH
/ Bf CHz Me CHz OCHZCHZOMe / OCH 2Ph Hz CHzCOOH
OCH2CH20Me CHz HN~N
H
BnN ~N H
Hz Formula III
Table 3 H H
Me H
I \ F
I \
-OH
/.
H
Br O
~~ OCH 2Ph CHZCHz"O' ~ OCH2CH20Me CH2CH2"NHMe O
~II H
CHZCHZ"NMe2 O
H
CHZCH ~N
Formula N
Table 3a H H
Me H
F
-OH
H
H
/ Bf Hz OMe CHz OCHzCHzOMe / OCH2Ph Hz OCHZCOOH
OCH2CH20Me CHz HN
H
Hz BnN \ H
CH~z Formula N
Table 4 H H
Me H
\ F
-OH
OH
Br HZ-\ -NH2 ~II~ OCH 2Ph CHZCH2 _O' OCH2CH20Me CHZCH ~NHMe ~ H
CH2CH2"NMez ~ H
CHZCHz' _N
Formula V
Table 4a Rat H H
Me H
F
/ -OH
CHz H
\
/ Bf OMe \
CHZ
CHZCHZOMe / OCH2Ph CHZ
CHZCOOH
OCH2CH20Me CHZ
H
H
CHz Bn~N H
Cf H/I~'z Formula V
Table 5 R R
H H
Me H
\ F
-OH
OH
Br H ~-\ -NH2 OCH2Ph CHyCH ~O~
~ OCH2CH20Me CHZCHz _NHMe O
~II H
CH2CH2"NMez ~ H
CHZCHZ' -N
Formula VI
Table Sa R Rib H H
Me H
F
/ -O H
CHz H
/ Br CHZ
Me CHZ
CHZCH20Me / OCH2Ph CHZ
CHzCOOH
OCH2CH20Me CHz H
CHZ
Bn~N H
ICH/I~z Formula VI
Table 6 R7 i H H
Me H
I \ F
I \
-OH
OH
Br Hz-I \ -NH2 O
~II~ OCH2Ph CH2CHZ _0-~II OCH2CH20Me CHZCHZ _NHMe ~ H
CHZCHZ"NMez ~ H
CHZCH2"N
Formula VII
Table 6a OZNHz Rtb /
R~
N
Formula VII
R7 Rib H H
Me H
F
/ -OH
OH
/ Br CHZ
Me CHI
CHZCHZOMe / OCH 2Ph CHZ
OCH2CH20Me CHZ
HN
H
CHZ
Bn~N H
C[H/I~z Table 7 Formula VIII
A D A D
OZNHz HzNMez F
/ \ / \ / \ / \
CI
OzNHMe / \ / ~ / \ / \
F
OzNHBu(t) / \ / ~ / \ / \
CI
OZMe F
/ \ / \ / \ /-\
F
HzNH F
/ \ / \ Hz / \
F
H2NHMe H
z / \ / ~ / \
F
Table 8 A D A D
OZNHz HZNMeZ F
/ \ / \ / \
CI
OzNHMe / \ / ~ / \ / \
F
OZNHl3u(t) / \ / ~ / \ / \
CI
OZMe F
/ \ / \ / \ / \
F
HZNH F
/ \ / \ HZ % \ /-\
F
HZNHMe Hs / \ ~ ~ / \
F
wherein R3 is a member selected from the group consisting of H, F, -OH, Formula IX
Br, Cl, -NHz, -O-CHz-O-Ph and -O-CHZ-CHz-O-CH3, Table 9 Formula X
A D A D
OZNHz HzNMez F
/ \ / \ / \ / \
CI
OzNHMe / \ / ~ / \ / \
F
OpNHBu(t) / \ / ~ / \ / \
CI
O2Me F
/ \ / \ / \ / \
F
/ \ / \ HZ % \ /-\
F
H NHMe / \ 2 / \ H / \
F
Table 10 Formula XI
A D A D
OZNHx HzNMex F
CI
OzNHMe /
F
OzNHBu(t) /
CI
02Me F
/ ~ / \
F
HxNHx F
Hx /
F
HZNHMe Hx / ~ / \ /
F
Table 11 Formula XII
A D A D
OZNHZ HZNMe2 F
/ \ / \ / \ / \
CI
OZNHMe / \ / \ / \ / \
F
OZNHBu(t) / \ / \ / \ / \
CI
OzMe F
/ \ / \ / \ / \
F
HZNHp F
/ \ / \ HZ % \ /-\
F
HyNHMe Hx / \ / ~ / \
F
Table 12 Formula XIII
A D A D
OZNHZ HZNMez F
CI
OZNHMe /
F
OZNHBu(t) /
CI
02Me F
% ~ / \
F
HZNH F
HZ / ~ /-\
F
HzNHMe Hs / ~ / ~ /
F
Table 13 Formula XIV
A D A D
OpN Hz HzN Mez F
/ \ / \ / \ / \
C
OzNHMe / \ / \ / \ / \
F
OZNHBu(t) / \ / \ / \
/ \
ci OZMe F
/ \ / \ / \ /-\
F
HzNHz F
/ \ / \ Nhz / \
F
HZN H Me Hz / \ / ~ / \
F
Table 14 Formula XV
A D A D
OzNHz H2NMez F
/ ~ /
CI
OzN H Me / ~ /
F
OZNHBu(t) / ~ /
CI
OZMe F
/ ~ / ~ / ~ / \
F
HzNHz F
/ ~ / \ Nhz /
F
HzNHMe Hz / ~ /
N
F
Table 15 Formula XVI
A D A D
OZNHz HZNMez F
C
OZNHMe F
OzNHl3u(t) CI
OZMe F
F
HyNHp F
~ ~ ~ Nnz / ~ / \
F
HZN H Me HZ
F
Table 16 Formula XVII
A D A D
OzNHp HZNMez F
C
OpNHMe F
OZNHBu(t) CI
O2Me F
F
HzNHy F
NhZ
F
HZNH Me HZ
F
Table 17 02NH2 R1b' R1b"
\ ~ NH2 H ~
Formula XVIB
R7 ~ R11 ~ R1b' R1b"
H H H H
Me H H OH
\ \
F H
/ -OH F
C Hz OH
OH
\
/ OH OH
CHZ
H OMe I \ / -NH2 H
Table 18 OpNHz O / I \
\ /N
H
R~ R~~ NH2 Formula XX
R~ R~~ R~ R~~
H \
I I/
OH
H
Me H I /
CHz HZ_ OMe \ I/ I\ /
/ /
CHZ
Table 19 02NH2 _ / I \
FNi \ / N
R~ R~~ NH2 Formula XX
R~ R~~ R7 R11 H H I I /
/ CHx OH
H
Me H I /
CHZ
HZ_ Me I\ I/ I\ I/
/ /
CHZ
Table 20 OZNHZ / N~
\
NHz Formula XXII
R7_R~~ R~ R~~
\
H H I / I /
CHz OH
H
Me H I /
CHz Hz_ OMe I\ I/ I\ I/
/ /
CHz Table 21 OpNH2 / N~
/N
H R7 Rat NH2 Formula XXII
R~ R~~ R~ R~~
\
H H I
I/
/ CHz OH
H
Me H I /
CHz Hz_ OMe I\ I~ I\ /
/ ~
CHz Table 22 OzNH2 /
N
R~ R"
Formula XXIV
R~ R~ ~ R~ R~ ~
\ \
H H I / I /
CHz OH
H
Me H I /
CHz Hz. OMe \ / \ /
/ /
CHz Table 23 OZNHZ / N~
U N
R~ R~~
Formula XXIV
R~ R~~ R~ R~~
\
H H I / I /
CHz OH
H
Me H I /
CHz Hz_ OMe I\
I ~ I / I j /
Hz Table 24 02NH2 / ~ N
N
H R~ R»
Formula XXV
\ \
H H I / I /
CHz OH
H
Me CHz Hz_ OMe \ / \ /
/ /
~z Table 25 Rib, Rib..
02NH2 R~~ /
H
N \ NH2 R~ NI H
Formula XXVI
R7 ~ R11 ~ R1b' ~ R1b"
H H H H
Me H H OH
\ F H
/ ~/
/ -OH F
C HZ
OH
OH
\
/ OH OH
CHZ
H _ OMe 2 \
\ ~ / -NH2 H
/ CHz Table 26 OZNHZ Rib /
\ ~ NH2 H
Rya NH
Formula XXVII
Rya R7b Rya R7b \ \
H H I / I /
CHx OH
H
Me H I /
CHx Hx_ \ OMe I\ I/ I\ I/
/ / cHz Table 27 02NH2 Rib / ( \
\ /N
R7a NH2 Formula XXVIII
R7a R7b R7a R7b \
.H H I / I /
CHx OH
H
Me H I /
CHx Hx_ OMe \ / I\ I/
/ / CHx Table 28 02NH2 Rib /
H R7a NH2 Formula XXX
R7a R7b R7a R7b \ \
H H I / I /
CHx OH
H
Me H I /
CHx Hx. OMe I\ I/ I\ I/
/ /
CHx Table 29 02NH2 Rib /
H R7a NHp Formula XXX
R7a R7b R7a R7b H H I I /
/ CHx OH
H
Me H I /
CHx Hx_ Me I\ / I\ I/
/ /
CHx Table 30 OZNH2 O Rib /
R' 7a NH2 Formula XXXI
R7a R7b R7a R7b H H I / I /
CHz OH
H
Me H I /
CHz Hz_ \ OMe I\ I/ I\ I/
/ /
cHz Table 31 H
OZNHZ Rib / ~ N\
R7a Formula XXXII
R7a R7b R7a - R7b H I I/
/ CHz OH
H
Me H I /
CHz Hz_ \ OMe I\ I/ I\ /
/ /
CHz Table 32 H
02NH2 Rib / N
H ~ N
R7a Formula XXXIII
R7a R7b R7a R7b \
H
I~
CHy OH
H
Me H I /
CHz HZ. OMe I\ I~ ~\ I/
/
~z I~
Table 33 Rib, Rib.
R7b H \ NHZ
Rya HsC NH
Formula XXXIV
Rya ~ Rib ~ Rib' ~ R1b"
H H H H
Me H H OH
\ \
F H
/ ~ /
-OH F
CHZ
OH
H
/ OH OH
CHZ
H _ Me 2 \
\ I / -NH2 H
/ CHZ
-NH 2 Me H F
-NH Ac Me H H
NHS02Me Me H H
Table 34 02NHz Rib /
\ ~ NHZ
H I, K' a H3~
Formula XXXV
R7a ~ R7b H H
Me H
/ ~ /
CHz OH
H
CHz H - Me \ /
/ CHZ
-NH 2 Me -NH Ac Me NHS02Me Me Table 35 02NH2 Rib / ~ \
\ /N
Rya H3~ NH2 Formula XXXVI
Rya ~ R7b H H
Me H
\ \
/
/
/
cHz OH
H
CHz Me z_ \
/ CHz -NH 2 Me -NH Ac Me NHS02Me Me Table 36 02NHz Rib / N\
Rra Formula XXXVII
Rya H H
Me H
\ \
/ ~ /
\ ~ /
CHz OH
H
CHz _ Me z \
\ /
/ CHz -NH 2 Me -NH Ac Me NHS02Me Me Table 37 OZNH2 Rib ~ ~ S~
R'a H3C NH2 Formula XXXVIII
7b H H
Me H
\ \
/ ~ /
CHz OH
OH
CHz H _ Me \ /
/ CHz -NH 2 Me -NH Ac Me NHS02Me Me Table 38 02NHz Rib /
~a H3~ v NHp Formula XXIX
R7a ~ R7b H H
Me H
\ \
/ ~ /
/
CHZ
OH
H
CHz H - Me \
\ /
/ CHz -NH 2 Me -NH Ac Me NHS02Me Me Table 39 OzNH2 Rib / N\
N N
K' a Hg~
Formula XXXX
R7a ~ R7b H H
Me H
\ \
/ ~ /
CHi OH
OH
CHz H _ Me \ /
/ CHZ
-NH 2 Me -NH Ac Me NHS02Me Me Table 40 OZNH2 Rib / N
N
H
Rya H3C
Formula XXXXI
R7a ~ R7b H H
Me H
\ \
/ ~ /
/
/
CHZ
OH
H
CHy H - Me \ /
/ C
-NH 2 Me -NH Ac Me NHS02Me Me Table 41 H
Rib. Rib.
02NH2 Rib /
NHZ
v v Formula XXXXII
Rib ~ R» ~ Rib' ~ R1b"
H H H H
-C(= O)NCH 2CH 20C H3 H H OH
\ \
F H
-O H F
CHy OH
H
/ OH OH
CHZ
H2- Me \ / -NH 2 H
CHZ
-COOH Me H F
-COOC H3 ~ Me H H
-C(=O)N(CH3)2 ~ Me H H
Table 42 Formula Rib ~ R»
H H
-C(=O)NCH 2CH 20C H3 H
\ \
/ ~ /
CHZ
OH
H
CHz H - Me z \
\ /
/ CHZ
-COOH Me -COOC H3 Me -C(=O)N(CH3)2 Me Table 43 H
02NH2 Rib / ~ \
\ /N
R~~ NHz Formula XXXXIV
Rib ~ R~~
H H
-C(= O~1CH 2CH 20C H3 H
\ \
CHZ
OH
OH
CHi H - Me \ /
/ CHz -COOH Me -COOC H3 Me -C(=O)N(CH3)2 Me Table 44 H
02N H2 Rib HO / ~ N\
H Rig NHz Formula XXXXV
H H
-C(=O)NCH 2CH20CH3 H
\ \
/ ~ /
CHZ
OH
H
CHZ
H _ Me \ /
/ CHz -COOH Me -COOC H3 Me -C(=O)N(CH3)2 Me Table 45 02NH2 R~bHO / S
~H2 Formula XXXXVI
Rig H H
-C(= O)NCH 2CH 20C H3 H
\ \
\
~z OH
H
CHz _ Me \
\ /
/ CHz -COOH Me ~OOC H3 Me -C(=O)N(CH3)2 Me Table 46 02NHz O Rrd-10 / O\
N w ~ /
H v t~ ~H2 Formula XXXXVII
Rib ~ Rt ~
H H
-C(= O~1CH 2CH 20C H3 H
\ \
/ ~ /
CHz OH
H
CHz H - Me \ /
/ ~z POOH Me -COOC H3 Me -C(=O)N(CH3)2 Me Table 47 O pN H2 R~bHO /
N N
\/ \/ H " ~,"
Formula XXXXVIII
Rm H H
-C(=O)NCH 2CH20CH3 H
\ \
/ ~ /
CHZ
OH
OH
CHz H - 1 Me \ /
/ CHZ
-COOH Me -COOC H3 Me -C(=O)N(CH3)2 Me Table 48 OZNH2 R~bHO / H
N
N
Rtt Formula XXXXIX
Rte H H
-C(= O)NCH 2CH 20C H3 H
\ \
/ ~ /
\
CHi OH
H
CHy H _ Me / CHZ
-COOH Me -COOC H3 Me -C(=O)N(CH3)2 Me Table 49 Rib 02NH2 Rs Rib /
N \ ~ NH2 O Rya ~H
Formula L
R5 Rya ~ Rib ~ Rib H H H H
Me Me H
H
\ I Me /
HzC ~ ~ ~ / Bn OH
CHz H
\ _ / HyC ~ /N OMe CHz H - Me z \ _ \ / HZC
Ogn / CHz H , -CH 200H HzC ~ / OH OCH 2C0 OH
Me -CH 2CH 2COOM a HzC ~ ~ NHz OCH 2CH 20M a gn -CH2CH2CONMe2 HzC ~ ~ OH
Table SO
02NH2 Rs Rib /
N \ ~ NHZ
- _ O Rya ~H
Formula LI
Rs ~ R7a R7b H H H
Me Me H
\ \
Me / ~ /
Hzc ~ ~ ( / Bn CHz OH
\ _ / HZ°
CHz H _ Me z \ _ \ / Hz0 ~ N
/ CHz H -CH 200H Hz0 ~ / OH
Me -CH 2CH 2COOM a Hzc ~ ~ NHz gn -CH2CH2CONMe2 H2c Table 51 02NH2 Rs Rib / \
N \ ~ /N
R7a Formula LII
R5 ~ R7a ~ R7b H H H
Me Me H
\ I \ Me /
HZc ~ ~ ~ / en CHz OH
\ _ HZC ~ / N
CHz Me H i- \ _ \ / HZC ~ N
/ CHz H -CH 200H HaC \ / OH
Me -CH 2CH 2COOM a gn -CH2CH2CONMe2 H=c Table 52 H
02NHz Rs Rib / N\
_ w_ O Rya NH2 Formula LIII
Rs ~ R7a H H H
Me Me H
\ \
Me I/ I/
HzC ~ \ I / Bn CHz OH
\ _ CHz H _ Me \ / HzC ~ N
/ CHz H -CH 200H HaC ~ / OH
M HzC ~ ~ NHz -CH 2CH 2COOM a -CH2CH2CONMe2 Hzc Table 53 OZNH2 Rs Rib / S
~1~
O Rya NHZ
Formula LN
Rs ~ R7a H H H
Me Me H
\ I \ Me I/
Hzc ~ \ I / Bn CHz H
\ _ HZC
CHy H _ Me \ / HzC
N
CHz H -CH 200H HzC ~ / OH
M HOC ~ ~ NHZ
-CH 2CH 2COOM a gn -CH2CH2CONMe2 HZ°
Table 54 02NH2 Rs Rib / O
~N
O Rya NHZ
Formula LV
Rs ~ R7a R7b H H H
Me Me H
\ I Me I/
Hzc ~ ~ I / Bn CHZ
OH
\ _ I / H'° \ /
CHz H - Me 2 \ _ \ / HZC
N
/ CHZ
H -CH 200H HxC \ / OH
Me -CH 2CH 2COOM a gn -CH2CH2CONMe2 HzC ~ ~
_77_ Table 55 H
02NH2 Rs Rib / N\
R7a _ Formula LVI
Rs ~ R7a ~ R7b H H H
Me Me H
\ I Me /
H20 ~ ~ ~ / Bn CHz OH
\ _ HZC
CHz Me H z- \
\ / HZC
CHz H -CH 200H Hx0 ~ / OH
Me 2 ~ I 2 -CH 2CH 2COOM a gn -CH2CH2CONMe2 H2C
_78_ Table 56 02NH2 R5 Rib / H
N
N ~ N
R7a Formula LVII
R7a H H H
Me Me H
Me H2c ~ ~ I / Bn CHz H
\ _ HyC
CHz " _ Me z \ _ ~ / "Z~ \ /
/ N
CHz H -CH 200H "zc \ / OH
M "2C \ ~ N"z -CH 2CH 2COOM a ga -CH2CH2CONMe2 HZc \
Table 57 Rib 02NH2 I5 Rib /
N \ ~ NH2 O Rya ~H3 ~H
Formula LVIII
R5 ~ Rya ~ Rib R
H H H H
Me Me H
H
\ I \ Me F
I /
HZ~ ~ ~ I / Bn OH
~2 OH
\ _ / HZC ~ ~N OMe CHz H - Me \ / HzC
/ CHz N OBn H -CH 200H HzC ~ ~ OH OCH 2C0 OH
HzC Hz Me -CH 2CH 2COOM a ~ ~ OCH 2CH 20M a gn -CH2CH2CONMe2 Hzc ~ / OH
Table 58 OZNHZ R5 Rib /
N \ ~ NHz O Rya ~Hg ~H
Formula LIX
Rs ~ Rya Rib H H H
Me Me H
Me /
HZC ~ \ ~ / Bn CHZ
OH
\ _ HzC
CHz Me H y- ~ _ \ / HZC ~ N
/ CHz H -CH 200H HxC ~ / OH
Me -CH 2CH 2COOM a HzC \ / NHZ
gn -CH2CH2CONMe2 Hzc Table 59 02NH2 I5 Rib / \
N \ ~ /N
7a H3~ ~H2 Formula LX
R7a ~ R7b H H H
Me Me H
\ \
I / I / Me HZc ~ ~ I / Bn CHZ
H
\ _ / HzC
CHZ
MB
H 2- \
\ / HzC
N
/ CH=
H -CH200H HZc ~ ~ ~H
Me ~ HzC ~ ~ NHZ
-CH 2CH 2COOM a gn -CH2CH2CONMe2 H=c Table 60 H
OZNH2 R5 Rib / N\
w_ Formula LXI
R5 ~ R7a H H H
Me Me H
\ I Me I/
Hz0 ~ \ I / Bn CHz OH
\ _ HZC
CHz H - Me \ / HzC ~ N
/ CHz H -CH 200H HzC ~ / OH
Me -CH 2CH 2COOM a Hz0 \ / NHz Bn -CH2CH2CONMe2 HZ°
Table 61 OzNH2 R5 Rib /
N I /N
O Rya H3C NH2 Formula LXII
R7a R7b H H H
Me Me H
\ \
Me I/ I/
HZC ~ ~ I / Bn CHZ
OH
\ _ HzC
CHI
H - Me \
\ / HZC
N
/ CHI
H -CH 200H HaC \ / OH
Me -CH 2CH 2COOM a HzC \ / NHZ
gn -CH2CH2CONMe2 HZ~
Table 62 OZNH2 RS Rib /
~\N
O Rya H3C NHp Formula LXIII
R7a ( R7b H H H
Me Me H
\ \
Me HZc ~ ~ ~ / Bn CHZ
OH
\ _ HZC
CHp H - Me \ / HZC
N
/ CHy HZC ~ ~ OH
M H2C ~ ~ NHz -CH 2CH 2COOM a gn -CH2CH2CONMe2 H,c Table 63 H
OZNH2 R5 Rib / N\
U ~N
O
Formula LXIV
R7a ~ R7b H H H
Me Me H
\ \
/ / Me HOC ~ ~ I / Bn CHZ
OH
\ _ / HyC
H _ Me \ / HzC
N
H -CH 200H HzC ~ / OH
Me -CH 2CH 2COOM a HzC ~ ~ NHz gn -CH2CH2CONMe2 HZC
Table 64 H
02NH2 Rs Rib / N' ~NH2 N
O Rya H3C
Formula LXV
Rs ~ R7a R7b H H H
Me Me H
\ I Me I/
H2~ ~ ~ I / Bn CHZ
OH
\ _ / HzC
CHz Me H 2_ \
\ / HpC
N
/ CHZ
H -CH200H H2C ~ / OH
M HZC ~ ~ NHS
-CH 2CH 2COOM a gn -CH2CH2CONMe2 HZO
_87_ Table 65 Rib H
02NH2 I5 Rib /
N \ ~ NH2 O R~~
Formula LXVI
R5 R7b R~~ ~ 1b R
H H H H
Me Me H
H
\ I Me F
/
Hz~ ~ ~ ~ / Bn OH
~z OH
\ _ / HZC ~ /N OMe CHZ
H - Me \ / HZ° ~ I
/ CHZ N OBf1 H -CH 200H HsC \ / OH OCH 2C0 OH
HxC NHz Me -CH 2CH 2COOM a ~ ~ OCH 2CH 20M a -CH2CH2CONMe2 Hz~ ~ ~ OH
_g8_ Table 66 N
O
Formula LXVII HN~ 'NH2 R7b ~ R1~
H H H
Me Me H
\ \
Me / ~ /
Hzc ~ ~ I / gn CHz OH
\ _ / HzC
CHy H z- Me \ / H2C ~ N
/ CHz H -CH 200H HxC \ ~ OH
Me -CH 2CH 2COOM a HzC \ / NHz -CH2CH2CONMe2 H=c Table 67 OZNH2 5 ~bHO / \
N R \ ~ /~
Formula LXVIII
Rs ~ Rib ~ R~~
H H H
Me Me H
\ \
I I / Me HZc ~ ~ I / Bn CHz OH
\ _ / HzC
CHz H _ Me z \
\ I / HzC ~ N
/ CHz H -CH 200H HzC ~ / OH
Me 2 ~ I
-CH 2CH 2COOM a gn -CH2CH2CONMe2 HZc Table 68 OZNHz Rs R~t~NO / N\
w ~ /
O R» v NHZ
Formula LXVIX
Rs H H H
Me Me H
\ \
Me I/ I/
HzC ~ \ / Bn CHz OH
\ _ / HzC
CHI
H - Me \
\ / HzC
N
/ CHz H -CH 200H HzC \ / OH
Me HzC ~ ~ NHz -CH 2CH 2COOM a -CH2CH2CONMe2 H,c Table 69 OzNHz Rs R~bHO
w O » v NH2 Formula LXX
Rs ~ Rib ~ Rtt H H H
Me Me H
\ I Me /
H~~ ~ ~ ~ / Bn CHz H
\ _ HzC
CHZ
H - Me \ / HzC ~ N
/ CHZ
H -CH 200H HxC \ / OH
Me -CH 2CH 2COOM a HzC ~ ~ NHZ
gn -CH2CH2CONMe2 HZ~
Table 70 w_ ~ /
O R» NHz Formula LXXI
H H H
Me Me H
\ I Me /
HZC ~ \ ~ / Bn CHz H
\ _ CHZ
Me H Z- \
\ / HzC
N
/ CHz H -CH 200H HaC \ / OH
Me -CH 2CH 2COOM a HzC \ / NHz -CH2CH2CONMe2 H2C
Table 71 02NH2 Rs R~t~O / N\
N
O
Formula LXXII
H H H
Me Me H
\ \
I / I / Me Hzc ~ ~ I / Bn CHz OH
\ _ HZC
CHz H - Me \ / H2C
N
/ CHz H -CH 200H HzC ~ / off Me -CH 2CH 2COOM a -CH2CH2CONMe2 H2c Table 72 02NHZ RS R~bHO
~NH2 N
O R~~
Formula LXXIII
R5 ~ Rib ~ R~~
H H H
Me Me H
\ \
I I / Me I\
H2c ~ \ / Bn CHz OH
\ _ / HzC
CHz H _ Me z \ _ \ / Hzc N
/ CHz H -CH 200H HzC ~ / OH
M HzC ~ ~ NHz -CH 2CH 2COOM a gn -CH2CH2CONMe2 Hzc Table 73 / SOxNHz SOZNHx /
\ \ / \ I \ Me /
I / N \ I NHz / \ I NHx / SOZNHx /
I \ I / SOxNHx O
\ \ / \I II
\ home /
~N \ I NH Iz I / N \ I NHz O NH
O NH
/ SOZNHx /
\ I \ N / SOZNHx i \ / I
I / N \ I NHz \ \ /
O NH / N \ I NHx O NH
Table 74 / SOzNHZ / SOpNHz \ \ H H \ \ H Bn / N \ / N \
o I / o ~
HN' ~NHp HN ~ ~NH, / SOzNHz Me0~0 SO NH HO O
/ ~ z z \ \ \
'\~H
/ N \
o ~ / o HN' ~NHz HN NHz / SOzNHz \
/ N ~ / SOsNHz O ~ ~ ~ \ \
H
N / N
O
HzN ~N
Other preferred compounds of formula I, having the sub-formula Ia, are set forth in Table 75, below.
Table 75 Formula Ia R~
o-z- z x - Phenyl- m_C~_ z o-x- x z -P m- z - _ enY
o-z- z -p enYl o-z- z z ~- P~ m-Ct=~ z o_z- z 3_ _phenyl W -C(=NH)NHZ
o-z- z z n_ eny m~(= z _p o x- z x p m-C(=O)NHx = eny o-r x z -p m_ eny o-z- x x -p m~~-0)~Z
eny o-x- z z 3_ p m_ eny o-z- z z j- -p eny m- x o-x- z x n_ eny m- z _p -o-x- z z a p- -~~z o-z- x x me P' z o-z- x z -am p- x me o-z- z x 3-am p-C
me o-z- x x a- P- z a o-z- z z n_ p_ x _~
me o-z- x z me p- x o-x- z x -am p-~,(=V)Nttx me o-z- x z -am p- x me o-z- z z 3-am p_ x me o-x- z x 3- p- x -am me o-z- x z n_ p- z _~
a o-r z x eny m- IVH)NHZ
-ammo-car oxy is acid o-SUz-Nriz H LHx m-rnenyt-ammo m- z carboxylic acid o-SUx-NHz H ~:Hx r-pnenyt-ammo m- z carboxylic acid o-SUx-NHx H c:Hz Ltt3-pnenyt-ammo m-~(=riri)r~riz carboxylic acid o-5Ux-NHx H c:Hx LH3-U-phenyl m-V(=rrri)r~rix ammo carboxylic acid o-SUz-NHz H c:Hz tsn-u-pnenyi m-~(=r~ri)wriz ammo carboxylic acid o-5Ux-NHx H c:Hz rnenyt-ammo m-~(=u)r~rix cardoxyttc acid o-SUz-NHz H c:Hx L1-pnen yt-ammo m-~(=v)Nriz carboxy lic acid o-SUz-NHx H c:Hz r-pnenyt-ammo m- z carboxylic acid o-SUx-NHx H ~ c:Hz c:H3-phenyl-ammo m- x carboxylic acid x c m (~)~x uo carboxylic a d o-5Ux-NHz H (:Hz tin-u-pnenyi-ammo m-~;(=u)Nrix carboxylic acid o-z- x z a m- =NH N
y z p enoxy-acetic aci ester o- z- 2- H CHz Mettryl m-C(=NH)NHz - Cl-phenoxyacehc acid ester o- z z H CHz Methyl m- z F-phenoxy-acetic acid ester o-5Uz-Nriz H LHz Metnyi m- z ~ri3-pnenoxy-acetic acid ester o-5Uz-NHz H LHz Metnym:rij-u-pnenoxy- m- z acetic acid ester o-SUz-NHz H c:Hz Memyi m- z tsn-u-pnenoxy acetic acid ester o- r z CHz Methyl m- z Yhenoxyacehc acid ester o- z- z CHz Methyl m-C(=V)NHz C1-phenoxyacehc acid ester o- z- z z a m- z y -p enoxyacehc acid ester o-5Uz-NHz H c:Hz Memyi m- z t.H3-pnenoxy-acetic acid ester o-SUz-NHz H (:Hz a m- z y -p epoxy acetic acid ester o-SUz-NHz H (:Hz a m- z y n--p epoxy acetic acid ester o- z- z z enoxyacetic m- z aci o- z z z -p m-(:(=NH)NHz epoxy-acetic aci o- z- z z -p m- z epoxy-aceric aci o- z- z z 3-p m- NHz epoxy-acetic aci o- r z z 3- m-C(=NH)NHz -p epoxy-acetic acid o- z- z z n- m- z -p epoxy acetic aci o- z- z z enoxyacehc m- z aci o- z- z z -p m-(:(=U)NHz enoxyacehc aci o- r z z -p m- z enoxyacehc -aci o- z- z z 3- p m- z epoxy-aceric aci o- r z z 3 m- z -p epoxy acetic acid o- z- z z n- m- z -p epoxy acetic aci o- z z z enoxye m-~;~=mryvriz ano o- z- z z -p m- z epoxy-a ano o- z- z z -p m-C~~H)NHz epoxy-a ano o- r z z j-p m- z epoxy-a ano o- z- z z 3- p epoxy-a m-- ano o- z- z z n- epoxy a m- z -p ano o- z- z z enoxye m- z ano o- z- z z -p m- (=O)NHz enoxye ano o- r z z -p m- z epoxy-a ano o- z- z z j-p m-~:~=u)ivriz epoxy-a ano o- z- z z s- P epoxy- m- z - a ano o- z- z z n_ epoxy- a m-~:~=u~ivriz _p ano o- r z z a m- z y p epoxy-a y ether o-SUz-NHz H c:Hz Metnyi m- z Li-pnenoxyetnyi ether o-SUz-NHz H Lriz Metnyi m- z r-pnenoxy-emyi ether o-~Uz-NHz H c:Hz Memym;ti3-pnenoxy- m-~~=mryvriz ethyl ether o-5Uz NHz H c:Hz nnetnyi m- z ~ri3-u-pnenoxy-ethyl ether o-SU2 NHz H LHz 1\necnyi m- z tin-u-pnenoxy ethyl ether o-z- z z a m-~~=u)wriz y ienoxye y ether o-5U2-NH2 H l;Hz Metnyll:l-pneriOXyeLtlyl m-l:(=u)1Vt12 ether O-5UZ-NHZ H ~riz Memyi m-~~=u)Nriz r-pnenoxyeuiyi ether O-5Uz-NHZ H laiz Mettlyl m-~;ti3-phenoxyethylether o-5V2 Hz H LHz lmemym:ri3-u- m-~~=v)wriz N
phenoxyethyl ether o-5Uz-Nriz H calz lvlemyl m- z tsn-u-phenoxyethyl ether o-i z z- z P m- z enY
o-z- z z- z -P m- z enY
o-z- z r z -P m-C(=1QH)NHz enY
o-z- z H z- z 3 P m- z enY
o-i z z z 3- - p eny m- _ o-z- z z- z n_ eny m- z _p o-z- z z- z P z enY
o-z- z r z -P m-~l=~)~nz enY
o-z- z z- z -P m- z enY
o-r z r z a-P m- z enY
o-i z z- z 3- p eny m- =O
-o-r z z- z n_ eny m-~~=~)r~riz _p o-z- z z z me P- z o-z- z z- z -am P-CC ~~z me o-i z i z -am p- z me o-z- z r z 3-am p-C(=NH)NHz me o-z- z z- z 3 p- z -am me o-z z z z n- p-C(_~)~z -am me o-z- z z- z m p-C(=O
me o-z- z z- z -am p- z me o-z- z z- z me p-t~(=u)ivtiz o-z z i z 3-am p-~.~=u)mriz me o-z- z z- z 3- p- z -am me o-z- z z- z n_ p- z _~
me o-z- z z- z eny m-C~ NH)NHz -ammo-car oxy is acid o-5Vz-NHz H (:Hz-~:Hz eny m- z -ammo carboxylic acid o-SUz Hz H C:Hz-C:Hz r-phenyl-ammo m-~~=~ri)~ry N
carboxylic acid o-5Uz-NHz H c:Hz-ca1 y ; m- z 3-pnenyi-ammo carboxylic acid o-SUZ-NHZ H l:Hz-I:HZ 1x13-u-pnenyi m-~.~=mri)mriz ammo carboxylic acid o-5Uz-NHz H C;Hz-c:Hz rip-u-pnenyi m-~~=~ri)~riz ammo carboxylic acid o-SUz-NHz H C:Hz-LHz rneny-ammo m- z carnoxync acid o-5Uz-NHz H C:Hz-LHz Li-pnenyi-ammo m- z carboxylic acid o-5Uz HZ H C;HZ-l:Hz r-pnenyi-ammo m-~~=v)wriz N
carboxylic acid o-SUz-NHz H LHz-LHz LH3 m-~~=u)Nriz pnenyi-ammo carboxylic acid o-SUz-NHz H c:Hz-Ltiz LH3 m-~~=u)r~riz u-pnenyi-ammo carboxylic acid o-SVZ HZ H l:Hz Hz nn-u-pnenyi-ammo m-~~=u)Nriz N l;
carboxylic acid o-z- z r z a m- z y p epoxy-acetic aci ester o- z- z z z et m-C(=NH)NHz y -p enoxyacehc acid ester o-SOz-NHz H CHz CHz Methyl m- z r'-phenoxy-acetic acid ester o-JUz-Nriz r1 LHz-MHz lvletnyl m- z LH3-pnenoxy-acetic acid ester o-~uz-NHz H t,tiz-l:rizMemyi m- z cai;
u-pnenoxy-acetic acid ester o-JUz-Nriz ti t;Hz-~Hz Memyi m-~~=r~ri)wriz tsn-u-pnenoxy acetic acid ester o- z- z H CHZ CHz Methyl m-(:(=U)NHz Yhenoxyacehc acid ester o-SOz-NHz H CHz-CHz Methyl m-C(=U)NHz C1-phenoxyacehc acid ester o- z- z H CHz-CHz Methyl m- z F-phenoxyacehc acid ester o-JVZ NHz H lalz-lalz lVlelllyl m- z l;tij pneriOXy-acetic acid ester o-SUz-NHz H Lrlz-LHz a m- z y -p enoxy acetic acid ester o-5Uz-NHz H LHz-t:Hz a m- z y n--p enoxy acetic acid ester o- z z H - z- z enoxyacehc m- z - aci o- z- z z- z -p m- ~ NH)NFIz enoxy-acetic aci o- z- z z- z -p m- z enoxy-acetic aci o- z- z r z 3- p m- )NHz enoxy-acetic aci o- z- z r z 3- m-C(=NH)NHz -p enoxy-acetic acid z- z z- z n- m- z -p enoxy acetic aci o- z- z z- z enoxyacehc m-C(=O)NHi aci o- z- z z- z -p m- z enoxyacehc aci o- z- z z- z -p m-C(=O)NHz enoxyacehc aci o- r z z- z 3-p m- z enoxy-acetic aci o- z- 2 2 2 3- m- =O)NHZ
-p enoxy acetic acid o- z- z z- z n- m- z -p enoxy acetic aci z- z z- z enoxye m-ano o- z- z z- z -p m- =NF~NHz enoxy-a ano o- z- z z- z -p m- z enoxy-a ano o- z- z z- z 3 p m- =NH)NHz enoxy-a ano o- r z z- z s- - p enoxy-a m- z ano o- z- z z z n- enoxy a m--p ano o- z- z z- z enoxye m-C(=O)NHz ano o- z- z z- z -p m- z enoxye ano o- z- z z- z -p m- =O~I2 enoxy-a ano o- z- z z- z 3- p m- z enoxy-a ano o- z- z z- z 3- - p enoxy- m-~a=ul~riz a ano o- z- z z- z n- enoxy- a m- z -p ano o- z- z z z a m-C(=NH)NHz Y
p enoxy-a y ether o-5Uz-NHz H ~;Hz-~;ttz lviemyl m- z t,i-pnenoxyemyi ether o-5Uz-Nriz H c:Hz-t;Hz Memyi m- z r-pnenoxy-etnyi ether o-SUz-NHz H (aiz-c:Hz a m- z y 3-p enoxy-ethyl ether o-~Uz-Nriz H l;Hz-C.;HZ lVleTtlyllalg-u-prieriOXy- m-l:(=1Vri)iVriz ethyl ether o-5Uz-NHz H LHZ-~:HZ nnemyi m- z tsn-u-pnenoxy ethyl ether o-z- z z- z et m-y enoxye y ether O-JVZ-Nrlz t~ Lty-~tiz Metnym;i-pnenoxyemyi m-~;(=U)Ntiz ether o-i z i z a m- z y -p enoxye y ether o-JVZ-Nrlz z- z a m- z Y
phenoxyethyl ether o-JUZ-Ntly t1 1a12-lalz MeLtlyll:rl3-U- m-l;(=U)NriZ
phenoxyethyl ether o-~uz-Nriz t m :riz-~riz nnemyi m-~:(=U)ririz nn-U-phenoxyethyl ether o-z- z z- i z P m- z enY
-o-z- z z- z-z -phenyl m_C~_~)~z o-z- z z- z-z ~en~ iri_C(=NH)NFIz - -z- z z- z-2 3_ p m_~( eny -~z o-z- z z- z-z 3- - p eny m- z o-z- z z- z-z n_ eny m_C(=~z _p o-z- z i i z p m- z eny o-z- z z- z-z -P m-C(=
enY
o-i z r r z -P m- z enY
o-i z z- z-z s- P m- z enY
z- z r i z 3- - P eny m--. -o_z_ z z_ z_z n_ eny~ m-C(=O)~2 _p o-z- z z- z-z m p_ z me - i z i i z -and p-C(=NH)NH2 me -_ o-z- z z- z-z -am p-C(=~)~z a o-z- z z- z-z 3-am p_ z me z- z i z-z 3- p--am me o-r z i i z n- p_ -am me o- : z i i z m p-C(=O)NH2 me o-z- z z- z-z -am p- z me o-z- z r z-z -am p- z me o-i z z- z-z 3-am p-C(=O)NHz me o-z- z z- z-z 3- p- z -am me o-i z i z-z n_ p_ z _am me o-i z i z-z eny m--ammo-car oxy is acid o-5U2-Nllz r1 LH2-~'H2-Lri2~l-rnenyi-ammo m- z carboxylic acid o-5Uz-Ntlz t1 Lrlz-~:riz-t,rtzr-pnenyi-armno m- z carboxylic acid o-~Uz-Nriz t m aiz-~aiz-~aizt,ti3-pneny-ammo m-~;(=r~riJmriz carboxylic acid o-JVZ-Nri2 ti LHr~ Hz-~nz ~H3 m-~(=wri)wriz u-Pnenyi ammo carboxylic acid o-JUZ-Ntlz ti l:riz-1;r12-1;ri2tsn-U-pneny m-L(=Nri)Nriz ammo carboxylic acid O-JUZ-NHz ti caiz-caiity rneny-ammo m-~(=U)r~riz q carooxync acid o-z- z i r z -P m- z enY
-~o carboxylic acid O-JUz-Nt12 t1 1:r12-C;riirizr-pnenyl-ammo m- y C;
carboxylic acid o-~UZ-NHz t1 ~:riz-c:r12-(:rtzLri3-pnenyl-ammo m-carboxylic acid o-~Uz-Ntiz ti l:riz-l;riz-c:rizl:rl,-U-pnenyi-ammo m- z carboxylic acid o-~Ui rlz ri trrtz-~tlz-Lrlznn-U-pnenyi-ammo m- z N
carboxylic acid o-z- z z- z-z a m- z y p enoxy-acetic aci ester o-z- z r z-z a m- z y -p enoxyacehc acid ester o-SOz-NHz H C;HZ Hz-CHz Methyl m-C;(=NH)NHz (: l-phenoxy-acehc acid ester O-DUz-Nriz H urirunruriz Memy1 m- z t;li3-pnenoxy-acetic acid ester o-JVz-Nriz tt ~tiz-~:riz-~;tiz Metnyi m-~:~=mrywriz t_;ti3-u-pnenoxy-acetic acid ester O-JVz-Nriz H ~riz-Lnr~-nz nnetnyi m- z nn-u-pnenoxy acetic acid ester o-z- z H CHz-CHz-CHz a m- z y enoxyacehc acid ester o-z- z H CHz-CHz-CHz Methyl m-C;(=U)NHz C1-phenoxyacehc acid ester o-z z - H CHz-CHz-CHz a m- z - y -p enoxyacehc acid ester z z z- z-z a m- z Y
s-p epoxy-acetic acid ester O-SVZ-NHZ H caiz-cai2atz a m- z ~ y -p epoxy acetic acid ester o-SUz-NHz H c:Hz-c:HzWaiz imetny m-~:~=u)mriz tsn-u-pnenoxy acetic acid ester o-z- z z- r z enoxyacehc m- z aci o-z- z z- z-z -p m- z epoxy-acehc aci o-z- z z- z-z -p m-epoxy-acehc aci o-z- z z- z-z 3- p m- z epoxy-acehc aci z- z z- z-2 3- m- )NHz -p epoxy-acehc acid o-z- z z- z-z n- m- z -p epoxy acehc aci o-z- z z- r z enoxyacehc m-C;(=U)NHz aci z- z r z-z -p m- z enoxyacehc aci o-z- z r z-z -p m-C(=O)NHz enoxyacehc aci o-z- z r r z ,-p m- z epoxy-acehc aci o-r z r z-z 3- m--p epoxy acehc acid o-z- z z- r z n- m- z -p epoxy acehc aci o-z- z z- z-z enoxye m-ano o-z- z z- z-z -p m-epoxy-a ano o-z- z z- z-z -p m- z epoxy-a ano o-z- z z z-z s- p m-epoxy-a ano o-z- z z- z-z 3 -p m- z epoxy-a ano o-z- z r r z n- ~(~lHjNHz -p epoxy a ano o-z- z r z z enoxye m- z ano o-r z z- r z -p m- (=O)NHz enoxye ano o-z- z r z-z -p m- z epoxy-a ano o-z- z z- z-z 3 p m- NHz epoxy-a ano r z z- z-z ,- - p epoxy- m-C(=O)NHz a ano o-z- z r z-z n- epoxy- a m- z -p ano o-z- z z- z-z a m-y p epoxy-a y ether o-5uz-NHz H ~tiz-t,tizaiz Memy m-~~=mryvriz ~ m-pnenoxyewy ether O-5V2-NHZ H 1:H2-C;HZ-l;HZ lVleLCly1 m-l.:(=lVt1)lVtlz r-pnenOXy-elllyl ether o-z- z z- z-z a m- z Y
epoxy-ethyl ether o-JVz-NHz ti ~;tiz-~atz-taiz a m- z y -p epoxy-ethyl ether o-~u2 Hz t~ utiz-utiz-t.riz a m- z N y n--p epoxy ethyl ether o-z- z r z- z a m- z y enoxye y ether o-5Uz-NHZ H lalZ-I:HZ Hz Mettlyl m-l: l:l-pnenoxyemyt ether o-SUz-Nriz H 1;H2-1:H2-1:H2 nnetnyi m- z r-pnenoxyemyi ether o-~Vz-NHz H t:rlitiz-~;tiz iviemyl m- z ~; t;n3-phenoxyethyl ether o-SUZ-NHZ H C:HZ-lalzH2 Melllyl m-~:(=V)lVrlz 1; 1:H3 v-phenoxyethyl ether o-SUz-NHz H LHZ HZ tiz Metnyl m-~~=~)wnz ~ ~ tsn-u-phenoxyethylether o-z- z z- s P m- z - enY
o-z- z z- 3 -p m- z - eny o-z- z z- s -p m-C(=NIT)NHz - eny o-z z z- s 3- P m- z ' enY
o-z- z z- 3 s- - P eny m_ -o-z- z z- s n- eny m- z - -p o-r z z- s P m- ~z - enY
o-z- z Z 3 _p m_ - eny o-z- z z- 3 -p m- (=O)NHz - eny --o-z- z r 3 3-P m-C(=O)~z - enY
o-r z z- s s- P eny m_ z - -o-z- z r s n- eny m- NHz - -p o-z z z- 3 m p-C(=NH)NHz - me o-z- z z- s -am p_ z - me z- z 2- g -am p-l.~=lvn)lVn2 - me o-2 2 z- 3 3-am p-C(=NH)NHz _ me 2- 2 z- 3 3- p_ - _am me o-z- z z- s n- p- (=NH)NHz - -am me o-z- z z_ 3 i p~(=O~z - me o-z- z z_ 3 -am p-~:~=~)mnz _ me o-r z z- 3 -am p-C(=O)NHz - me o-z- z z- 3 3-am p-~:(=m)mnz - me o-r z z- 3 3- P_ z - -am me o-i z z- j n- p_ z - -am ' me o-z- z z j eny m-- -ammo-car z oxy is acid o-z- z z- , eny m-C(=NH)NHz _ -ammo carboxylic acid o-z- z z- 3 -p iri~(=NH)NHz _ eny -ammo carboxylic acid o-i z z- s s-P m-~.t=ivn)ivnz - enY
-o carboxylic acid o-~ z z ' carboxylic m ~z ac d ~o o-z- z z- 3 n- m-C(~7I-I)NHz _ _p eny ammo carboxylic acid o-z- z z- 3 eny m~(=O)NHz - -ammo car oxy is acid o-z- z z- 3 -p m-~(=O)NHz - eny -ammo v1 carboxylic acid o-z- z r 3 m-C(=O)NHz -p eny -ammo carboxylic acid o-z- z z- 3 m_C(=O)NHz - ~r11 s-P
enY
-ammo carboxylic acid o-i z r s 3 m-~~=~)wnz - -p eny -ammo carboxylic acid z- z z- s n- m- =O)NHz - _p eny -ammo carboxylic acid o-z- z z- s a m-- y p enoxy-aceric 1i-J
aci ester z- , et m- z J V 11 - ry o-1V z -p z- enoxyacehc acid ester o-r z r s a m-C;(=NH)NHz - y -p epoxy-acetic acid ester o-5Uz-NHz H ~;tiz-Ltil-~;ti3)-a m- z y 3-p epoxy-acetic acid ester o-5Uz-NHZ H Caly-fail-1:ri3)-nnetnymri3-U-pnenoxy- m- z acetic acid ester o-5Uz-NHz H 0.112-l;tll-l:rig)-nnetnyi m- z tsn-v-pnenoxy acetic acid ester o-z- z CHz-CH(-CH3)-Methyl m-C(=U)NHz Phenoxyacehc acid ester o-z- z CHz-CH(-CH3)-Methyl m-C(=U)NHz C1-phenoxyacehc acid ester o-Z z H CHz-CH(-CH3)-Methyllr-phenoxyacehc m- z acid ester o-5Uz riz H c:riz-~til-~ti3)-Mecnyi m- z N ~ri3-pnenoxy-acetic acid ester o-z- z z- s a m- z - Y
;
-p epoxy acetic acid ester o-SUz Hz H c:Hz-cail-Lti3)-a m- z N y n--p epoxy acetic acid ester o-r z z- 3 enoxyacehc m- z - aci o-z- z z- 3 -p m- (--NH)NHz - epoxy-acetic aci o-r z z- 3 -p m-- epoxy-ace c aci o-z- z z- a 3- p m- z - epoxy-acetic aci o-z- z z- 3 ,- -p m-t,l=~ri)mriz - epoxy-ace c acid o-z- z z- 3 n- m- NHz - -p epoxy acetic aci o-z- z z- 3 enoxyacehc m- z - aci o-z- z z- 3 -p m-C(=O)NHz - enoxyacehc aci o-z- z z- 3 -p m-C;(=U)NHz - enoxyacehc aci o-z- z z- a ,- p m-- epoxy-acetic aci o-z- z z- 3 3- -p m- z - epoxy w v,l,l acetic acid o-z- z z- 3 n- m-C(=O)NHz - -p epoxy acetic acW
o-z- z z- 3 enoxye m-- ano o-z z z- 3 -p m- =NH)NHz - epoxy-a ano o-z- z z- 3 -p m- z - epoxy-a ano o-z- z z- 3 3-p m- (=NH)NHz - epoxy-a ano o-z- z i- s 3- m- z - -p epoxy-a ano o-z- z z- 3 n- m- (=NH)NHz - -p epoxy a ano o-z- z z- s enoxye m-~,~=U~mriz - ano o-r z z- 3 -p m- =O)NHz - enoxye ano o-z- z r 3 -p m- z - epoxy-a ano o-r z z- s s- p m- z - epoxy-a ano o-z- z z- j 3- -p epoxy- m-C~ OjlVHz - a ano o-z- z z- 3 n- epoxy- a m-~;l=U)r~riz - -p ano o-z- z z- s a - y v~ my p m- z epoxy-a y ether o-z- z r s a - Y v.~ .w~
-p m-enoxye y ether o-z- z z- , a m- NHz - Y v~ ...y -p epoxy-a y ether o-r z z- s a m- )NHz - Y ,.~ ..
s-p epoxy-ethyl ether o-z- 2 2 3 a m- )NHz - Y ,_,~ ., s--p epoxy-ethyl ether o-z- z r 3 a m- =NH)NHz - y n--p epoxy ethyl ether -o-z- z z- 3 et m- z - y enoxye y ether o-~uz-Nriz z- 3 a m- z - y -p enoxye y ether O-JUz-Ntiz ti ~rii -~ri3l-Memyi m- z ~ry r-pnenoxyecnyi ether o-5Vz tiz n z- a a m- z N - Y
s-phenoxyethyl ether i z r s m-C(=O)NHz - ma ua a ~aa v a Y
n-phenoxyethyl ether o-z- z Me~TSri-~- m-C(=O)NHz ~aa -v..aa ~aa~ ~
z- 3 -phenoxyethyl ether o-z- z r z P m- z - enY
o-z- z z- z -p m-~;l=mtyvriz - eny o-r z z- z -p m-C(=NH)NHz - eny o-z- z z- z r P m-C(=NH)lQHz - enY
o-r z z- z 3- - P eny m~( ~)~z -o-z- z z- z n- eny m-t.;(=mtiyvtiz - -p -o-z- z z' z p m-C(=O)NHZ
- eny o-z- z z- z -p m- z - eny -.
o-z- z z- z -p m-C(=O)NHz - eny~
e-z- z z- z s-P m-C(=OjNHz - enY
r z z- z 3- m- (=O)NH2 - -p eny o-z z r z n- m-~.l=vyvriz - -p eny o-z- z z- z m p- z - me o-i z z- z -am p-C(=NH)NHZ
- me o-z- z r z -am p-~:l=mtiJmtiz - me o-r z z- z 3-am p-C(=NH)NHz - me a- z z z s- p- z - -am me o-z- z z- z n- p- z - -am me e-z- z z- z i p-C(=O)NHz - me o-z- z z- z -am p-~:l=v)ivtiz - me z- z z- Z -am p- z - me o-z- z z- z ,-am p-t:l=vyvriz - me z- z z- z 3 p- (=O)NHz - -am me z- z z- z n- p-C(=O)NHz - -am me z- z z- z eny m-~.~=mryvriz - -ammo-car oxy is acid o-z z z- z eny m-C(=NH)NHz - -ammo w.a a as a carboxylic acid o-z z z- z -p m-C(=~I)NHz - eny -ammo a-as a carboxylic acid o-z z z- z m-C(=NH)NHz - v..aa as a 3-p eny -ammo carboxylic acid o-z- z z- z 3- m- z - -p eny ammo carboxylic acid o-z- z z- z n- m- (=NH)NHz - -p eny ammo carboxylic acid o-z- z z- z eny m- z - -ammo car oxy is acid O-JUZ-Nriz ti uriz-ury-Nriz~-m-pnenyi-ammo m-~l=v~Nriz carboxylic acid O-JVZ tiz r~ uriz-pry-Nriz~-r-pnenyi-ammo m-~l=vyvriz N
carboxylic acid o-~u2 tiz m ;riz-~:ry-mtiz~-~;ti3-pnenyi-ammo m-~;l=vyvriz N
carboxylic acid o-~uz-Ntiz r~ uriz-ury-Nriz~-~ri3-u-pneny-ammo m-~l=~Jwriz carboxylic acid O-JVZ riz t m ;riz-~:ry-Ntiz~-nn-v-pneny-ammo m-~:l=vyvriz N
carboxylic acid r z z- z a m- z - y p enoxy-acetic aci ester o- z- z z- z - a m- z Y
-p enoxyacehc acid ester o-SOz-NHz H CHz CH(-NHz)-Methyl m-C(=NH)NHz l~'-phenoxy-acetic acid ester o-auz-Ntiz tt ~tiz-pry-tvtiz)-Merry m-~~=wri)wriz ~ri3-pnenoxy-acetic acid ester o-~uz Ntiz ti ~ri2-pry-Nriz)-Memyi m-~(=wri)wriz ~ri3-u-pnenoxy-acetic acid ester o-~Vz-Nriz ti ~tiz-Sri(-Ntiz)-Memyi m- z tsn-u-pnenoxy acetic acid ester o-S~2-NHz H CHz CH(-NHz)-Methyl m- z Yhenoxyacehc acid ester o- z- z H CHz CH(-NHz)-a m- z y -p enoxyacehc acid ester o- z- z -- H CHi CH(-NHz)-a m- z y -p enoxyacehc acid ester o-5uz-NHZ H l;Hz-lai(-1Vt12)-a m-y 3-p erioxy-acetic acid ester O-5uz-NHz H LHz LH~-Ntiz)-Metnyi m- z ~ti3-u-pnenoxy acetic acid ester o-5uz-NHZ H (:Hi C:H~-Ntlz)-Metnyl m-tin-u-prieriOXy acetic acid ester o- z- z z- z - enoxyace m- z c aci o- z- z z- z - -p m-C(=NFI)NHZ
epoxy-acetic aci o- z- z z- z - -p m- )NHz epoxy-acetic aci o- r z z z - 3- p m-C(=NH)NHz epoxy-acetic aci o- z- z z- z - 3- m- z -p epoxy-acetic acid o- z- z z- z - n- m- z -p epoxy acetic aci o- z- z z- z - enoxyacehc m- (=O)NHz aci o- r z z- z - -p m-C(=U)NHz enoxyacehc aci o- z- z z- z - -p m- .(=~NH2 enoxyacehc aci o- z- z r z - 3- p m- z epoxy-acetic aci o- z z z- z - 3- m- (=O)NH2 -p epoxy acetic acid o- z- z z- z - n- m- (--~NHZ
-p epoxy acetic aci o- z- z z- z - enoxye m- (=PHjNHz ano o- z- z z- z - -p m-~;~=ivri)ivriz epoxy-a ano o- z- z z- z - -p m- (=NH)NHz epoxy-a ano o- z- z z- z - 3- p m- z epoxy-a ano o- z- z z- z - s- - p epoxy-a m- NHz ano o- z- z z- z - n- epoxy a m- z -p ano o- z- z z- z - enoxye m- z ano o- z- z z- z - -p m-~;~=u)ivriz enoxye ano o- z- z r z - -p m- (=~)NHz epoxy-a ano o- z- z z- z - j p m- z , epoxy-a ano o- z- z z- z - s- - p epoxy- m- z a ano o- z z z- z - n_ epoxy- a m_ _p ano o- z- z z- z - a Y y myw p m-epoxy-a y ether o- r z z- z - a m- z Y
-p enoxye y ether o-JVz-Nriz H ~tiz-qty-Ntiz)-Merry m-~~=wri)wriz r-pnenoxy-emyi ether o-~Vz-Nriz tt ~riz-cay-Ntiz)-nnemyi m- z ~ri3-pnenoxy-ethyl ether o-~uz NHz tm atz-Lty-mtiz)-memym;ri3-u-pnenoxy- m-~~=mri)mnz ethyl ether o-5uz-NHz ti ~nz-~ril-Nnz)-Merry m-~~=wri)mriz tsn-u-pnenoxy ethyl ether -o-z- z z- z et m- z - y enoxye y ether O-JUz-Nriz l 2 a m- z - y -p enoxye y ether _ - z a rn=C(=O)NHz as _ y _phenoxyethyl-ava w a n-ether o-z- z z_ z a m- )NHz - y w.~ v 3__ ma ua m.aa phenoxyethyl ether _ _ CHz_ ~ a m-C(=O)NHz y phenoxyethyl ether O-JUz-Ntiz ri ~riz-Sri(-wriz)-Memyi m-~;l=a nn-u- yvtiz phenoxyethyl ether o-z- z r n p m- z - enY
o-z- z z - -p m-~l=mri~wriz n eny -o-z- z z- _ -p m- z n eny _ --o-z- z z- - ~: m- (=~)~z n 3-phenyl -o-r z z- - 3 p eny m-C(=~~z n --o-z- z z- - n_ eny m- z n _p -o-z- z z- - p m- =O)~z n eny -o-r z z- _ -p m- z n eny _ o-z- z 2 - -p m- z n eny -o-r z z- - 3- p m_ -O)NHZ
n eny -o-r z z- - 3_ _ p eny m- z n -o-z- z z- - n_ eny m- z n _p _ -o-z- z z - me p- z n -o-r z z- _ -am p_ =NH)NHz n me _ o-z- z z- _ -am p- z n me _ o-z- z z - 3-am p=CC ~~z n me -o-z- z l - 3- p- z n -am - me o-r z z- - n_ p- )NHz n _am - me o-z- z z- - m p-C(=O)NHz n me -o-z- z Z - -am p- z n me -o-z- z z- _ -am p_ =O)~2 n me _ o-z- z z- - 3-am p- z n me -o-r z z- - 3_ p_ =O)NHz n _~
- me o-z- z z- - n_ p- z n _am - me o-z- z Z - eny m- (=NH)NHz n -ammo-car - oxy is acid o-~u2 riz ti ~riz-~ry-~snlw;i-rneny-ammo m-~l=wryvriz w carboxylic acid O-JUz-Ntiz m aiz-pail-nn~-r-pnenyi-armno m-~;l=mryvriz carboxylic acid z- 2 2- ' 3-p m- z n eny - -ammo carboxylic acid o-~uz-Ntiz ti ~riz-aril-~snl-~rij-u-pnenyi m-~l=ivrilwriz ammo carboxylic acid O-JVZ-Nri2 t m aiz-Ltil-tsn~-tsn-u-pnenyi m-~:l=mryvriz ammo carboxylic acid o-JVz-Nri2 t-~ z - eny m- z n -ammo - car oxy is acid O-JVZ-lVri2 z- _ -p y -ammo m- z n en _ carboxy lic acid o-~u2 tiz t-~ ~riz-qty-tsn~-r-pnenyi-ammo m-~l=u~wriz N
carboxylic acid O-JVz riz t~ ~riz-t,ril-tsn~-t_;ri3-pneny-ammo m-~:l=uyvriz N
carboxylic acid O-JUZ ttz ri z- n 3 m- z w - -p eny -ammo carboxylic acid -o-z z CHz-CH(~n~-~n=O-p~amW m-C(_O)~z o carboxylic acid o-z- z z- - a m- z n y - p enoxy-acetic aci ester o-SUz-NHz z- - n - a m- z ry -p enoxyacehc acid ester o-SUz-NHz H CHz-CH(-Bn)-Methyl m- z r-phenoxy-acetic acid ester o-1Vz-Ntlz ti lalz-fall-tSn)-Merry m-ul=wriJwriz ~ri3-pnenoxy-acetic acid ester o-JVz-Ntlz H lily-fall-tSn)-MeLllyl m- z 1.ri3 u-pnenOXy-acetic acid ester O-JVz-Nriz H Ltiz-Ltil-tsnJ-a m- z y n_ -p epoxy acetic acid ester o-SOz-NHz H CHz-CH(-Bn)-Methyl m- z Yhenoxyacehc acid ester o-SOz-NHz H CHz-CH(-Bn)-Methyl m-C(=U)NHz C1-phenoxyacehc acid ester o-SOz-NHz H CHz-CH(-Bn)-Methyl m-C(=U)NHz r'-phenoxyacehc acid ester O-JUz-wHz H ~riz-aril-tsnJ-enemy m-~l=uJwriz ~ri3-pnenoxy-acetic acid ester O-JVZ wHz ti ~riz-aril-tsnJ-nnemyi m-~l=uJwriz uri,-u-pnenoxy acetic acid ester O-JVZ Ntiz ti ~tiz ~ty-rsnJ-Merry m-~,l=vJivriz tsn-u-pnenoxy acetic acid ester o- z- z z- - n - enoxyacehc m- z aci o- z- z z- - n - -p m-C(=NH)NHz epoxy-acetic aci o- r z r - n - -p m- z epoxy-acetic aci o- z- z z (->3n)= CH3-pherioXy-acetic m-C(=NH)NHz acid o- z- z z- - n - 3- m-C(=NH)NHz -p epoxy-acetic acid o- z- z z- - n - n- m- z -p epoxy acetic aci o- z- z z- - n - enoxyacehc m-aci -o- z- z z- - n - -p m- z enoxyacehc aci o- z- z z- - n - -p m-C(=O)NHz enoXyacehc act o- z- z z- - n - j m- z p epoxy-acetic aci o- z- z z- - n - 3- m- (=O)NHz -p epoxy acetic acid o- z- z z- - n - n- m- z -p epoxy acetic aci o- z- z z- - n - enoxye m- z ano o- z- z z- - n - -p m-C(=NH)NHz epoxy-a anol o- z- z z- - n - -p m- z epoxy-a ano o- i z z- - n - s- p m-epoxy-a ano o- z- z r - n - 3- _ p epoxy-a m- z ano o- z- z z - n - n- epoxy a m- z -p ano o- z- 2 z- - n - enoxye m-~l=uJwriz ano o- z- z 2 - n - -p m- z enoxye ano o- z- z z- - n - -p m-~-- NHz epoxy-a anol -o- z- z z- - n - s- P m- z epoxy-a ano o- i z z- - n - 3_ _ p epoxy- m-~:l=uJivriz a ano o- z- z 2 - n - n- epoxy- a m- z -p ano o- r z z- -Bn)- ~~p~enoXy-ethyl m=C( NH)NHz ether ~'JVz lVttz z- - n - a m- z y -p enoxye y ether o_JVz'lvriz 2 - n - a m- z y -p epoxy-a y ether o-~uz-Nriz r~ z - n - a m- z y s-p epoxy-ethyl ether o- ~ z H 2 - n - et m-C(=NH)NHz y -p epoxy-ethyl ether o-~uz-wriz rm :riz-~:ry-rsnJ-Merry m-~l=ivriJivriz rsn-v-pnenoxy ethyl ether o-z- z Z- - n a m- z - y enoxye ry ether o-~uz-Ntlz tl ~tlz-gall-tsn)-lvlemyl;l-pnenoxyemyl m-~,(=v)lvrlz ether O-JVz-Nrlz ri l:riz-l;rll-lin)-Nlelllyl m- z r-prienOXyeUlyl ether o-JVz-Nliz z- - n a m- z - Y
a-phenoxyethyl ether o-JVz-Ntlz r1 ~rlz-~rll-lsn)-l vlemyl ~r13-u- m- z phenoxyethyl ether o-JVz-Nrlz r1 urlz-Vrll-lsn)-l vlemyllsn-u- m- z phenoxyethyl ether O-JUz-Nriz n calz-fall-~alz-p m- z eny COOCH3)-O-JUz-Nriz tl z- z- -p m- z eny COOCH,)-O-5Vz-Nriz tl cali :rlz-r-pnenyl m-~:(=Nrl)lvrlz Ltll-~
COOCHj)-o-5Vz-Nriz z- z- 3-p m- z eny COOCH3)-O-JUz-Ntlz ti C;tiz itiz-3- m- z fall-l -p eriy COOCH,)-O-JUz-Nriz ri ~riz-aril-~riz-n_ m- z -p eny COOCH3)-O-JUz-Nriz tl ~riz-~rll-~rlz-pnenyl m-~l=v)lvrlz COOCH,)-O-JUz-Nrl2 ti l:rlz-fall-lalz-t_;1-prienyl m-~:l=v)lVrlz COOCH3)-o-z- z i z- -p m- z eny COOCH3)-o-~uz tlz tt alz-gall-~tlz-~;t13=pnenyl m-~:(=u)lvrlz N
COOCH3)-o-~u2 tiz z z- s- m- z N -P
eny COOCH,)-o-~u2 tlz z- z- n- m- z N -p eny COOCH,)-o-~Uz-Ntiz z- z- m p- i me COOCH,)-o-~u2 rlz z- z- -am p- z N me COOCH,)-o-~u2 rlz z z- -am p- z N me COOCH3)-z 2 z- s-am P- z me COOCH,)-o-JUz-Nriz rl l:rlz ;tiz-j_ ~p- z fail-l _am me COOCH3)-o-~u2 tlz rl ~r12 rlzrsn-u-anllme p- z N ~rll-~
COOCH3)-O-JVz-Nriz ~;tlz alz-m p- z t~tll-~ me COOCH3)-.
o-aVz tlz rl ~rlz rlz-~l-anllme p-~l=~)lvrlz N aril-~
COOCH3)-o-~uz ttz rl ~rlz-~rll-~rlz-r-anllme p-~l=u)lvrlz N
COOCH,)-O-JVZ-lvriz ri ~riz-tall-~riz-~:r13-anlnne p-~:(=v)lvrlz COOCH,)-O-JUz-Ntiz n l:ri2lall-l;tiy-lalg-V-an111I1e p-l.l=V)Nrlz COOCH3)-o-r z r z- n- p- z -and me COOCH,)-o-~Vz-Ntlz ri Lnz-Lnl-~riz-rnenyl-amino-carooxync m-~:l=Ntl)lvtlz COOCH,)- acid o- r z z- z- eny -ammo ..,~ .wy..
m- z COOCH3)- carboxylic acid o- z- z z- z- -p m-~(=rVryr~riz eny -ammo COOCH,)- carboxylic acid o-SUZ NHz r1 Ltiz-Lti(-Ltiz-LH3-pnenyi-ammo m-~(=~ryr~riz COOCH3)- carboxylic acid O-JUz-Ntiz t~ ~riZ ~;ri(-~riz-~ti3 m-~(=mry~riz u-pnenyi ammo COOCH3)- carboxylic acid O-JUz-Ntiz t~ ~riz-Sri(-~riz-~sn-u-pnenyi m-~(=wti~mriz ammo COOCH3)- carboxylic acid o-aV2 NHz ri ~tiz-Sri(-~riz-rnenyi-ammo m- z carooxyiic COOCH3)- acid o-~UZ NHz ti z- z- -p y -ammo m- z en COOCH3)- carboxylic acid o-~Vz NHz H ~alz-~a1(-~;tlz-r-pnenyl-ammo m-t.(=u)rVriz COOCH3)- carboxylic acid o-JVz NHz W a1z-Lt1(-~;tlz3 m- z P
enY
-ammo COOCH3)- carboxylic acid o-~Uz-NHz W ;tlz-~t1(-~;ttZ3 m- z -p eny -ammo COOCH,)- carboxylic acid o-JU2-Ntl2 t1 lalz-l;tl(-1;112-n_ m- z -p eny -ammo COOCH3)- carboxylic acid o- z- 2 H CHz-CH(-CHz-a m- z y p enoxy-acehc COOCH3)- acid ester o- 2-NHz H CHz-CH(-CHz-Methyl m-C;(=NH)NHz C;1-phenoxyacehc COOCH3)- acid ester o-SUz-NHz H CHz-CH(-CHz-Methyl m- z t'-phenoxy-acehc COOCH;)- acid ester o-JUZ-Nriz m ;tiz-jai(-taiz-nnewym:ri3-pnenoxy- m-~~=mry~riz COOCH3)- acetic acid ester o-SOz-NHz H CHz-CH(-(:HZMethyl m-(:(=NH)NHz (:H3-U-phenoxy-COOCH3)- acetic acid ester o-~uz NHz ti Ltiz ~ty-~ry-Merry m-~(=wrywriz tsn-u-pnenoxy COOCH3)- acetic acid ester o-SUz-NHz H (:Hz-C:H(-(:Hz-Methyl m-C;(=U)NHz Yhenoxyacehc COOCH,)- acid ester o-SOz-NHz H C;Hz-(:H(-C;HZMethyl m- z (:1-phenoxyacehc COOCH,)- acid ester o-SOz-NHz H CHz-CH(-(:Hza m- z y -p enoxyacehc COOCH3)- acid ester o-~uz-Ntiz tW a~z-~a~(-tatz-a m- z y s-p epoxy-COOCH3)- acetic acid ester O-JUz-Ntiz ri ~;riz-Sri(-~:riz-a m- z Y
-p epoxy COOCH3)- acetic acid ester O-JVZ-Nriy m ;tiz-Sri(-~aiz-Memyi m- z tsn-u-pnenoxy COOCH3)- acetic acid ester o-SOz-NHz H C;Hz-(:H(-C;Hz-enoxyacehc m- z aci COOCH3)-o- z- z z- r -p m- z epoxy-acehc aci COOCH3)-o-SUz-NHz H C;Hz-(:H(-C;Hz-r-phenoxy- m-C:(=NH)NHz acehc acid COOCH,)-o-SUz NHz H C:Hz-(:H(-C;Hz-(:H3-phenoxy-acehc m- z acid COOCH3)-o-SU2 NHz H C;Hz-C;H(-(;Hz-(:H3-U-phenoxy-acehc m-(:(=NH)NHz COOCH,)- acid o-SOz NHz H C:Hz-C:H(-C:Hz-Bn-U-phenoxy m-C:(=NH)NHz acehc acid COOCH3)-o-SUz-NHz H (:Hz-(rH(-(:Hz-Yhenoxyacehc m-(:(=U)NHz acid COOCH3)-o- z- z r z- -p m- z enoxyacehc aci COOCH3)-z r r -p m-(:(=U)NHz J V enoxyacehc o-z- aci COOCH3)-o-SOz-NHz H (:Hz-C;H(-C;HZ C:H3-phenoxy-acetic m-C;(=U)NHz acid COOCH,)-o-2-NHz H z- z-3 m- z J V -p enoxy acetic COOCH,)- acid o-z-NHz H (:Hz-CH(-CHz-Bn-O-phenoxy m-C;(=U)NHz acetic acid COOCH,)-o-~urNHz H t.;Hz-LHlw;tirrnenoxyemanoi m-~l=wryrrriz COOCH,)-o-~u2-NHZ H MHz-~ry-~riz-~i-pnenoxy-emanoi m-~l=wri)ivriz COOCH,)-o-z Z z z--p m-enoxy-a ano COOCH3)-o-~u~ Hz H z- z-,-p m- z N enoxy-a ano COOCH,)-o-~u2 Hz ti LHz-~Hl-LHr ~ris-~-Pnenoxy-emanoi m-N
COOCH3)-o-SOz-NHz H (:Hz-C;H(-(:Hz-Bn-U-phenoxy m- z ethanol COOCH3)-O-JUZ-Nriz H lalz-l;ril-l;tiz-enoxye m-ano COOCH3)-O-~VZ-NHZ ti z z--p m- z enoxye ano COOCH,)-O-JVZ-NHz r1 t,Hz iz-r-pnenoxy-emanoi m-~:l=uyvriz ~;Hl-Lt COOCH,)-O-JVZ-Nri2 z- z-3 m-P
enoxy-a ano COOCH3)-o-5Uz Hz r z-3- m- z N -p enoxy-a ano COOCH,)-o-5Uz Hz H c:H2 z-tsn-u-pnenoxy- m-~:l=~yvriz N c:Hl-c:H emanoi COOCH3)-o-SUz-NHz H z- z-a m- z Y
P
enoxy-a y COOCH3)- ether o-5uz-NHz t1 c,H2 iz-metny m-t,l=mriyvriz c:Hl-ca m-pnenoxyetnyi COOCH3)- ether o-5u2 tiz H ~Hz-~til-~tiz-Mecnyi m-~l=mriyvriz N r-pnenoxy-emyi COOCH3)- ether O-5u2-NHz H cai2-LHl-LHz-Mewyl m-~ri3-pnenoxy-COOCH3)- ethyl ether O-5u2-NHZ H LHZ-LHl-LHz 1\netnyl m-~;l=rrryrrriz ~ti3-u-pnenoxy-COOCH3)- ethyl ether o-JVz Hz ti LH2-t.Hl-~aiz-Memyi m-N nn-u-pnenoxy COOCH3)- ethyl ether O-JVz-Nri2 t1 lal2 iz-nnemyi m- z ~;tilw;t rnenoxyemyi COOCH3)- ether O-JV2-Nt12 m ai? Ltil-taiz-nnemym;i-pnenoxyemyi m- z COOCH3)- ether o-JVz Hz H c:Hz-pail-~aiz-a m- z N y -p enoxye y COOCH3)- ether o-~uz-NHZ n ~riz-aril-~ri2a m- z y COOCH3)- phenoxyethyl ether O-JUZ-NHZ H 1;H2-l:H(-l;Hz a y 3- m-COOCH3)- phenoxyethyl ether o-JUZ-NHZ H l:Hz-Citl(-la12-l Vlemyl, tan-V- m-l~l=V)lVri2 COOCH3)- phenoxyethyl ether o-JUz-NHz H (:Hz-Ltll-t,tiz-pnenyl m-~l=mri)mriz CHZ-OH)-O-JUZ-NHZ ti 1,r12-fail-1x12-lLl-pnenyl m-l.l=lVr1)1vr12 CHZ-OH)-O-JVZ-NHz ri t_;tiz-aril-taiz-r-pnenyi m- z CHz OH)-z- z- z UV 111 11 v11 11 o- r z 3-p enY~
CHz-OH)-O-JVZ Nriz ri l:riz-l:ri(-l:tiZl:ri3-u-pnenyi m-~(=~riJNriz CHz-OH)-o_ z- z ri z- z- ri_ _p eny m- z CHz-OH)-o-~uz-Nriz rm :riz-l:ri(-l:riz-pneny m-~;(=u~~riz CHz-OH)-O-JUz-Nriz ri l:nz-l:ri(-c:riz_-p eny m- z CHz-OH)-o-~uz-Ntiz z- z- -p eny m- z CHz-OH)-O-JUz-Nriz 2- z- ,-p eny m- z CHz-OH)-O-JUZ-Nti2 H lily-lJtl(-l=t12-lJri3-u-pnenyi m-~(=vyvriz CHz OH)-O-JV2-Ntlz t1 1a12-lal(-1;11z-tSn-u-pnenyl m-l;(=V)Nrl2 CHz-OH)-O-JVZ Ntiz t1 1x12-l:ri(-1;ri2-Amlllle p-CHz-OH)-O-JVZ-Ntiz ri 1.r12-l:rl(-1x12-l.l-anllme p-l.(=lVt1)iVri~
CHz-OH)-O-lV2-NtlZ t1 l;tl2-l:ri(-lalz-r-anlllrie p-l;(=lVr1)Nriz CHZ OH)-O-JUZ-Ntl2 t1 1:ri2-l:ri(-l;tiz-lai3-amlme p-CHz-OH)-o-~VZ-Nriz ri laiz-Cai(-1.:t12-3- -aril me p-CHz-OH)-o-5Uz-Nriz ri z_ z_ n_ _yne p- z CHz-OH)-o-5Vz-Nriz ti l:riz-cai(-c.;tlz-amlme p-l:(=u~~ri2 CHz-OH)-o-5Uz Nliz z- z- -am me p- z CHz-OH)-O-5Vz-NHz Z- Z- -am me p-CHz-OH)-o-5U2 Ntlz H Ltiz-Cai(-laiz-1x13-amlme p-l:(=u)mriz CHz-OH)-O-JU2-Ntl2 H l;riz-l;ri(-1x12-3- -am me p-CHz OH)-o-JUz-Ntiz H l:tiz-lai(-laiz-n_ _am me p- z CHz-OH)-o-~UZ Ntiz ti calz-cal(-lalzrnenyi-ammo-caruoxyncm- z CHz OH)- acid O-JUZ-Ntlz H lalz-l,ti(-1,t12-l.l-Ynenyl-ammo m-l.(=lVr1)1Vr12 CHz-OH)- carboxylic acid O-~Uz-Ntiz tt l:nz l:ri(-l~riZ-r-pnenyi-ammo m-l:(=wry~riz CHz-OH)- carboxylic acid o-JU2-NHZ ri lalz-l:tl(-1x12-1;r13-pnenyl-ammom-l.(=Wri~lVriz CHz-OH)- carboxylic acid o-lU2-NHZ t1 1a12-l:ri(-lily-l;rlj-u-pnenyl m-l:(=LVri)lVrlz ammo CHz-OH)- carboxylic acid O-JUZ-NHz t~ cai2 Sri(-c:riz-tsn-u-pnenyi m-~(=wryrrriz ammo CHz OH)- carboxylic acid O-JUZ-Ntl2 ti laiz-l;ri(-layrnenyi-ammo carnoxyncm-l:(=uJNriz CHz-OH)- acid o-wz-Ntiz r~ l:riz-l:ri(-c:riz-l:upneny-ammo m- z CHz-OH)- carboxylic acid o-5uz-Ntiz n l:riz-l:ri(-caiz-r-pnenyi-ammo m- z CHz-OH)- carboxylic acid o-~uz-Ntiz t~ laiz-l:ri(-laiz-l:ri3-pnenyi-ammom-l:(=u~rrriz CHz OH)- carboxylic acid o-S02 NHz H z- z- 3- -p ieny -ammom- z ~.,.. ..~.~-....
CHz-OH)- carboxylic acid O-JVZ-lVtiz t1 1a12-l;H(-C:HZ-tiri-U-prienyi-ammom-C:(=V)NHZ
CHz-OH)- carboxylic acid o-JVz-Nriz H C:Hz-(:H(-(:Hz-Methyl phenoxy-aceticm-(:(=NH)NHz CHz-OH)- acid ester o-5Uz-NHz (:Hz-(:H(-(:Hz-Methyl (:1-phenoxyacehcm-(:(=NH)NHz CHz-OH)- acid ester o-5Uz-NHz C;Hz-(:H(-(:Hz-Methyl 1~'-phenoxy-m-C;(=NH)NHz acetic CHz-OH)- acid ester o- z- z z- z- a Y 3 p epoxy- m- z CHz-OH)- acetic acid ester O-~VZ-irriz ri ~:riZ aril-~riz-nnemyi ~ri3-u-pnenoxy-m-~:l=Nrywriz CHz-OH)- acetic acid ester o- z- z z- z- a y n- -p epoxy m- z CHz-OH)- acetic acid ester o-SUz-NHz r z- a y enoxyacehc m- z CHz-OH)- acid ester o-SUz NHz H (:Hz-(:H(-(:Hz-Methyl C:1-phenoxyacehcm-(:(=U)NHz CHz-OH)- acid ester o-SOz NHz H CHz-C;H(-C:Hz-Methyl F-phenoxyaceticm-C(=O)NHz CHz-OH)- acid ester O-JV2-lVtlz ri 1.ri2-lal(-1:ri2-Metnym:ri3-pnenoxy-m-t,(=u~Ntiz CHz-OH)- acetic acid ester O-JUz-ivriz ri ~riz-Sri(-~riz-ivieuiyi ~ri3-u-pnenoxym-~l=u)irriz CHz-OH)- acetic acid ester o-~uz Nriz ri uriz-~ry-~rizimeciiyi tsn-v-pnenoxym-~l=u)ivriz CHz-OH)- acetic acid ester o-SUZ NHz H (:Hz-C;H(-(:Hz-Yhenoxyacehc m-(:(=NH)NHz acid CHz-OH)-o-SOz-NHz H C;Hz-C;H(-(:Hz-C;1-phenoxy-aceticm-(:(=NH)NHz acid CHz-OH)-o-SOz-NHz H C;HZ (:H(-(:Hz--p epoxy- aceticm- z aci CHz OH)-o-SOz-NHz H C:Hz-(:H(-(:Hz-3-p epoxy-aceticm- z aci CHz OH)-o-SOz-NHz H C;Hz-C;H(-(:Hz-3- -p epoxy-aceticm- z CHz-OH)- acid o-SOz-NHz z- r ri- -p epoxy m- z acetic aci CHz-OH)-o- z- z r z- enoxyacetic aci m- z CHz-OH)-o-SOZ NHz H CHz-(:H(-C:Hz-C;1-phenoxyacehcm-C;(=U)NHz acid CHz-OH)-o-SOz-NHz H CHz-C:H(-C;Hz--p enoxyacehc m- z aci CHz-OH)-o-SOz-NHz H z- z 3-p epoxy-aceticm- z aci CHz-OH)-o-SOz-NHz H z- r s- -p epoxy aceticm- z CHz OH)- acid o-SOz NHz H (:Hz-(:H(-C;Hz-13n-U-phenoxy m-C;(=U)NHz acetic acid CHz-OH)-O-JVz-Nriz ri ~riz-aril-~riz-rnenoxyemanoi m-~l=ivri)Nriz CHz-OH)-O-JUz-Nriz ri ~riz-Sri(-~riz-~i-pnenoxy-emanoim-~l=ivri)~riz CHz-OH)-o-au2 NHz H ~tiz-~til-~;HZ-r-pnenoxy- etnanoim-~l=ivri)ivriz CHz-OH)-O-JVz-lVHz H 1;t12-l;ril-1a12-1;t13-prienOXy-elllanoim-l;(=lVt1)lVri2 CHz-OH)-o-~uz-ivHz ti r z- s- -p epoxy-a m- z ano CHz-OH)-- -H m- z JV 111 W 1 ~r11'-WL V 11 11 1 o- r z 1 n- -p epoxy et z- z- ano CHz-OH)-o-'uz-wriz r~ ~-riz-Lril-Lnrrnenoxyetnanoi m-~:l=uyvtiz CHz-OH)-O-JUZ writ ri ~riz-aril-~riz-m-pnenoxyemanoi m-~l=u~wriz CHz-OH)-O-JUZ-wriz ri ~riz-~:ril-t;tiz-r-pnenoxy-emanoim-~l=u~wtiz CHz-OH)-O-JUZ-writ ri ~nz-~nl-~-riz-~n3-pnenoxy-emanoim-~l=uJwriz CHz-OH)-O-JVz wriz r~ ~nz-~-nl-~-riz-~ri3-u-pnenoxy- m-ul=u~wriz emanoi CHZ OH)-o-~uz-wtiz z- r n- -p epoxy- m- z a ano CHz-OH)-o-wz-wriz m aiz-tJril-t,ry-memyi pnenoxy-etnyim-t,l=wrywriz CHz-OH)- ether o-~u2 wriz r z- a y -p enoxye m- z y CHz-OH)- ether o-auz-wriz z- z- a y -p epoxy-a m- z y CHz-OH)- ether o-JVz-writ Y r a Y s-p epoxy- m- z CHz-OH)- ethyl ether o-auz-wtiz m aiz-~;til-~aiz-Metnymai3-v-pnenoxy-m-~;l=wrywriz CHz-OH)- ethyl ether o-5uz wtiz t~ uttz-aril-uriz-enemy ~sn-v-pnenoxym- z CHz-OH)- ethyl ether o- Uz z r z- a y enoxye y m- z CHz-OH)- ether o-~uz wtiz m :ti? ~ailwaiz-nnetnyi m-pnenoxyemyim-~:l=~~wriz CHz-OH)- ether o-auz writ ri ~riz aril-~tiz-Memyi r-pnenoxyemyim-~l=u~wriz CHz-OH)- ether o-auz-wtiz ti tJtiz-~til-~aizMecny ~ti3- m- z CHz-OH)- phenoxyethyl ether o-~uz-wtiz t-~ uriz-aril-uriz-nnemyi urij-u- m-t,l=vlwriz CHz-OH)- phenoxyethyl ether o-~uz-wtiz t-~ uriz-aril-utiz-nnetnyi nn-v- m-~l=a yvriz CHz-OH)- phenoxyethyl ether o-~uz wtiz ti ~riz-~ril-~riz-pnenyi m-~l=mryvnz C(=O)-N-morpholino)-o-'uz-wtiz tm aiz-tail-~;tiz-~a-pneny m-~,l=wrywriz C(=O)-N-morpholino)-o-5uz-wtiz ti Lttz-~til-~tiz-r-pnenyi m-~l=wrywriz C(=O)-N-morpholino)-O-JVZ-wriz t~ t_;ttz-pail-~;ti2-~ai3-pnenyi m-i.l=mrtyvriz C(=O)-N-morpholino)-O-JVZ-wtiz tm aiz-Ltil-taiz-~;ri,-u-pnenyi m-~:l=mryvnz C(=O)-N-morpholino)-O-JVZ-wtl2 ti ~riz-~til-~riz-tsn-u-pnenyi m-~l=wriJwri2 C(=O)-N-morpholino)-O-JUz-wriz ri taiz-aril-~:riz-pnenyt m-~l=vyvriz C(-0)-N-morpholino)-O-JVZ-wriz t~ uriz-~til-uriz-m-pnenyi m-~l=v~wriz C(=O)-N-morpholino)-o- z H ~z-~ z- -p eny m-C(=O)-N-morpholino)-O-JUZ-lvriz ri ~riz-aril-~riz-trti3-pnenyl m-~:l=u)lrriz C(=O)-N-morpholino)-o-~uz-lvrlz ri ~rlz-aril-~rlz~r13-u-pnenyl m-~l=u)lrriz C(=O)-N-molpholino)-O-JUZ-ivriz ri t,riz-~;ril-~riz-rsn-u-pnenyl m-~:l=u)lVrlz C(=O)-N-morpholino)-O-JUz Nriz n ~riz aril-~riz-Anllme p-ul=lrri)lVrlz C(=O)-N-morpholino)-O-JUZ-lvriz n ~rlz-~rll-~rlz-~l-anllme p-~l=lrri)lrrlz C(=O)-N-morpholino)-O-JUz-lvriz n urlz aril-url2-r-anllme p-~l=lrri)lVrlz C(=O)-N-morpholino)-O-JUz-lvriz ri ~riZ ~til-~riz-~r13-amllne p-~l=lrti)lrriz C(=O)-N-morpholino)-o-auz-lvriz r1 urlz-unl-uriz-un3-u-amlme p-~l=lVri)rirlz C(=O)-N-morpholino)-O-JU2-1Vt12 H 1x12-l:rll-l=ri2-rsn-u-anllme p-~.l=mri)lrriz C(=O)-N-morpholino)-o-~uz-Nriz n uriz ~:ril-~riz-Amlme p-~l=u)lrriz C(=O)-N-morpholino)-o-~uz Ntiz ti aiz-~:ril-~aiz-~l-anllme p-~l=u)mriz C(=O)-N-morpholino)-o-~uz lvriz n ~riz ~;rll-~rlz-r-anllme p-~l=u)lrtiz C(=O)-N-morpholino)-O-JUz luriz n uriz aril-~riz-~ti3-amlme p-~l=u)lrriz C(=O)-N-morpholino)-o-au2lvtiz n urlz-aril-uriz-~r13-u-amlme p-~l=u)lvriz C(=O)-N-morpholino)-O-JU2-Nriz ti l:riz l;ril-lain-tfri-u-anllllle p-l;l=u)lVri2 C(=O)-N-morpholino)-O-JUz 1Vt12 ti l~rlz-l:rll-1;r12-Ynenyl-amino-CarDOXyIICm-l:l=lVt1)iVrl2 C(=O)-N- acid morpholino)-O-JUZ-lvriz ri trtlZ ~;ril-~:riz-~;1-rnenyl-aminom-~l=lxri)lrriz C(=O)-N- carboxylic acid morpholino)-o-~uz lurlz ti url2 ~;ril-~riz-r-pnenyl-amino m-~l=lrrl)lrriz C(=O)-N- carboxylic acid morpholino)-o-~u2lvtlz rl ~rlz-~rll-~rlz~ri3-pnenyl-ammom-~l=lrri)lrriz C(=O)-N- carboxylic acid morpholino)-O-~uz-Nriz ri c:riz-aril-~riz~ti,-u-pnenyl m-ammo C(=O)-N- carboxylic acid more o mo -o-SOz-NHz H - - z- n_ _p eny ammo m- z C(=O)-N- carboxylic acid morpholino)-o-wz-mriz n ~nz-~ril-~nz-rneny-ammo carooxyncm-~l=uyvriz C(=O)-N- acid morpholino)-O-~uz-mriz ri ~.riz-~:ri(-~riz-~;i-pnenyi-ammo m-~l=uyvriz C(=O)-N- carboxylic acid morpholino)-O-JUz-Nriz ri ~riz aril-~riz-r-pnenyi-ammo m-~l=uJwriz C(=O)-N- carboxylic acid morpholino)-O-JUZ-mriz ri ~:riz-~;ril-~;riz-~,ri3 pnenyi-ammom-~;l=vlivriz C(=O)-N- carboxylic acid morpholino)-o-~uz-lvtiz r~ ~;riz-pail-~;rizSri;-u-pnenyi-ammom-L(=u)Nriz C(=O)-N- carboxylic acid . moipholino)-o-~uz-mriz r~ ~riz-Sri(-~ri2~sn-u-pnenyi-ammom-~l=u~wriz C(=O)-N- carboxylic acid morpholino)-o-SUz-NHz H C;Hz-C;H(-CHz-Methyl phenoxy-aceticm-(:(=NH)NHz C(=O)-N- acid ester morpholino)-o-SOz-NHz H CHz-CH(-CHz-Methyl Cl-phenoxyacehcm-(:(=NH)NHz C(=O)-N- acid ester morpholino)-o-SOz-NHz H CHz-CH(-CHz-Methyl >~'-phenoxy-m-(:(=NH)NHz acetic C(=O)-N- acid ester moipholino)-O-JVz-Nriz H ~;Hz Lti(-~;tiz-Memyi Lti,-pnenoxy-m-~;l=mtyvriz C(=O)-N- acetic acid ester morpholino)-o-auz-ivHz t~ taizw;tyu;riz-tviemyi ~ri3-u-pnenoxy-m-~l=mryvriz C(=O)-N- acetic acid ester morpholino)-o-~uz-NHz m ;tiz-~;til-~;tizMetnyi ~sn-u-pnenoxym-~,l=mryvriz C(=O)-N- acetic acid ester morpholino)-o-SOz-NHz H CHz-CH(-CHz-Methyl Yhenoxyacehcm-C:(=U)NHz C(=O)-N- acid ester morpholino)-o-SUZ NHz H C;Hz-C;H(-(:Hz-Methyl (:l-phenoxyacehcm-(:(=U)NHz C(=O)-N- acid ester morpholino)-o-SOz-NHz H CHI CH(-(:Hz-Methyl r'-phenoxyacehcm-(:(=U)NHz C(=O)-N- acid ester morpholino)-o-~uz-Nriz r~ ~riz-aril-~riz-enemy ~ri3-pnenoxy-m-~l=vyvriz C(=O)-N- acetic acid ester morpholino)-o-~uz-Nriz ti ~riz pry-~riz-enemy ~ri3-u-pnenoxym-~l=u~wriz C(=O)-N- acetic acid ester morpholino)-o-~uz-wHz H ~riz Sri(-~riz-memyi rsn-u-pnenoxym-~l=u~wriz C(-0)-N- acetic acid ester morpholino)-o-SUz-NHz H C;Hz-(:H(-(:Hz-Yhenoxyacehc m-(:(=NH)NHz acid C(=O)-N-morpholino)-o- z- z z- r -p enoxy-acetic m- )NHz aci w.~ v~ m-morpholino)-o-SUz-NHz H CHz CH(-CHz-F-phenoxy- aceticm-C(=NH)NHz acid C(=O)-N-morpholino)-o-SUz-NHz H CHz-CH(-CHz-CH3-phenoxy-aceticm-C(=NH)NHz acid C(=O)-N-morpholino)-o-SUz-NHz H CHz-CH(-CHz-CH3-U-phenoxy-aceticm-C(=NH)NHz C(=O)-N- acid morpholino)-o-SUz-NHz H CHz-CH(-CHz-tan-U-phenoxy m-C(=NH)NHz acetic acid C(=O)-N-morpholino)-o-SUz-NHz H CHz-CH(-CHz-Yhenoxyacehc m-C(=U)NHz acid C(=O)-N-morpholino)-o-SUz-NHz H CHz-CH(-CHz-Cl-phenoxyacehc m-C(=U)NHz acid C(=O)-N-morpholino)-o-SOz-NHz H CHz-CH(-CHz-F-phenoxyacehc m-C;(=U)NHz acid C(=O)-N-moipholino)-o-SOz-NHz H CHz-CH(-CHz-CH3-phenoxy-aceticm-C(=U)NHz acid C(=O)-N-morpholino)-o-SOz-NHz H CHz-CH(-CHz-CH3-U-phenoxy m-(:(=U)NHz acetic C(=O)-N- acid morpholino)-o-SU2 NHz H CHz-CH(-CHz-Bn-U-phenoxy m-(:(=U)NHz acetic acid C(=O)-N-morpholino)-O-JVZ Nriz ti uriz-aril-uriz-rnenoxyemanoi m-~l=wrywriz C(=O)-N-morpholino)-o-~uz wtiz r~ ~riz-aril-~rizm-pnenoxy-emanoim-~l=wrywriz C(=O)-N-morpholino)-o-~uz-wtiz r~ ~riz-~ry-uriz-r-pnenoxy- emanoim-~l=wrywriz C(=O)-N-morpholino)-o-JUz-Nriz ti ~riz-~rtl-~:rlz-~;r13-pnenoxy-emanolm-~;l=wrywriz C(=O)-N-morpholino)-o-~uz-wtiz ti ~tiZ aril-~:riz-t_;ti3-u-pnenoxy-emanoim-t,l=mryvriz C(=O)-N-morpholino)-O-JVz-Nriz rm alz-Lrll-Lriz-~sn-u-pnenoxy m-~l=mryvriz emanoi C(=O)-N-motpholino)-o-~uz-Nriz ri ~riz-~nl-~nz-rnenoxyemanoi m-~l=v~wriz C(=O)-N-morpholino)-o-~uz-wtiz r~ ~riZ aril-uriz-~.;i-pnenoxyemanoim-~l=uJwriz C(=O)-N-morpholino)-o-~uz-Nriz r~ ~nz-uril-unz-r-pnenoxy-emanoim-c:l=ulwriz C(=O)-N-morpholino)-O-JUZ-ivriz ri ~riz-aril-tJriz-~ri3-pnenoxy-emanoim-~l=u~wriz C(=O)-N-morpholino)-o- z- z H CHZ- z- 3- -p ienoxy= m- )NHZ
vlll-trll ethano l.~' V
lJll V 1 1 C(=O)-N-morpholino)-O-JVz-iVriz ten -nz-~ril-Lnz-~n-u-pnenoxy- m-Ll=V~rrtiz emanoi C(=O)-N-morpholino)-O-JVz-Nriz ri ~riz-Sri(-~riz-Merry pnenoxy-eyum-ul=rrryNriz C(=O)-N- ether morpholino)-O-JUz-Nriz ri ~riz-Sri(-~riz-enemy m-pnenoxyemyim-ul=rrriJr~riz C(=O)-N- ether morpholino)-O-JVz-rrriz ri ~riz-aril-~riz-Memyi r-pnenoxy-emyim-~:l=mtiJr~riz C(=O)-N- ether morpholino)-O-JVz-rrriz ri ~riz-aril-~riz-nnetnyi ~ti3-pnenoxy-m-~;l=Ntyr~tiz C(=O)-N- ethyl ether morpholino)-O-JVz-Nriz ri tltiz-~;ri(-~:riz-Memym;ti3-v-pnenoxy-m-~:l=rVryvriz C(=O)-N- ethyl ether morpholino)-o-~uz-~tiz ti ~riz-~:ril-~;tizenemy nn-v-pnenoxym-~:l=rrryrVriz C(=O)-N- ethyl ether morpholino)-o-~uz-lvtiz ti LrirLril-Lnz-Memyl rnenoxyetnyim-~:l=~lrVriz C(=O)-N- ether moipholino)-~
o- z- z z- r enoxye y m- z a y -p C(=O)-N- ether morpholino)-o-~uz Ntiz ti ~riz uri(-~riz-Memyi r-pnenoxyemyim-~l=v~r~riz C(=O)-N- ether morpholino)-O-JVz-lVtlz h l:rlz-fall-laiz-Memym;ti3- m-~;l=V)r~riz C(=O)-N- phenoxyethyl ether morpholino)-o-~uz-Ntiz ti ~riz-aril-uriz-Memyi Sri; V- m-~l=V~r~riz C(=O)-N- phenoxyethyl ether morpholino)-o-~uz-Nriz ti ~riz-~:ril-uriz-nnemyi tsn-v- m-~l=V~rVriz C(=O)-N- phenoxyethyl ether morpholino)-O-JVz Ntiz t~ ~riz-~;ty-~;rtzpnenyi m-~:l=r~rywriz CHZ S(O)z-CH3 o-~uz-Nriz t-~ Ltiz-~:ril-trtiz-m-pnenyi m-t.l=rVrilrVriz CHz-S(O)z-CH3 O-JVz-Nriz ri ~ri2 ~;tt(-~tiz_-p eny m- z CHz-S(O)z-CH3 O-JUZ-Nriz z- z- 3-p eny . m- z CHz-S(O)z-CH3 o-~uz Nriz ri ~riz-aril-~riz~ri~-u-pnenyi m-~l=rrti~r~riz CHz-S(O)z-CH3 o-~uz ~riz r~ ~riz-aril-~rizrsn-u-pnenyi m-~l=r~ryrVriz CHz-S(O)z-CH3 O-JVz-t~riz ri ~riz-aril-~riz-p eny m- z CHz-S(O)z-CH3 O-~uz-Nriz ri ~riz-girl(-~riz-p eny m- z CHz-S(O)z-CH3 o-~uz Ntiz t~ ~tiz-Ltil-trtizr-pnenyi m-t_;l=vyvriz CHz-S(O)z-CH3 O-JVz rrriz n ~tiz-~;nl-~riz-Sri,-pnenyi m-~l=V~r~riz CHz-S(O)z-CH3 o- z- z I~ z- z- 3 -p ienyI m- z CHz-S(O)z-CH3 O-JUz-Nriz z- z- n- -p eny m- z CHz-S(O)z O-JUZ-Ntiz ri ~riz-~;ri(-t,riz-amime p-~;~=Nry~riz CHi S(O)z-CH3 o-~uZ Ntiz ~riz-~;ry-~;tiz~;i-amime p- z CHz-S(O)z-CH3 O-JUz Ntiz ti lalz-Lr1(-lalz-r-amlme p- z CHz-S(O)z-CH3 o-auz-Nriz ri ~riz-pry-~riz~:ri3-amime p- z CHz S(O)z-CH3 o-auz-Nriz tm :riz-qty-~tiz-~ai3 u-amnne p- z CHz-S(O)z-CH3 o-~uz Ntiz m :riz-~:ry-taiz-tsn-u-amime p-~~=NryNriz CHz-S(O)z-CH3 O-JUy-Ntiz n lalz l.rl(-t_;tlz-Hnllme p-l.~=u)Ntl2 CHz-S(O)z-CH3 o-~u2 Ntiz ri ~riz-pry-~riz-m-amime p-~~=u~Nriz CHz S(O)z-CH3 o-JUz NHz n t;rtz-Lti(-Lrlz-r-anllme p- z CHz-S(O)z-CH3 o-JUz-Nriz n c:riz-c:ri(-unz-~;rt,-amlme p- z CHz-S(O)z-CH3 o-~u2-Ntiz n ~tiz-~;ty-~;tiz-~;ri3-u-amime p- z CHz-S(O)z-CH3 o-~u2-Ntiz n z z- n- -am me p- z CHz-S(O)z-CH3 O-JUz-Ntlz ti caiz-~:rt~-caiz-rnenyi-ammo-carooxyncm-~~=mryNriz CHz-S(O)z-CH3acid o-JUZ-Ntiz ti l:rlz-Cat(-~:rlz-eny -ammo m- z CHz-S(O)z-CH3carboxylic acid O-SUz-NHz H ~;tiz-Lty-Ltiz-r-pnenyi-ammo m-~;~=NryNriz CHz-S(O)z-CH3carboxylic acid o-SU2 Ntiz H Caiz-c:11(-~;ttz-~;ri3-prienyl-ammom- z CHz-S(O)z carboxylic acid o- r z z- r s- -p eny ammo m- z CHZ S(O)z carboxylic acid o- z- z z- z- n- -p eny ammo m-~:~=NryNriz CHZ S(O)z carboxylic acid o-JUz NHz ri ~-riz-~-ril-~-riYrnenyt-ammo carooxyncm-~~=u~Nriz CHz-S(O)z-CH3acid o-~u2 NHz t1 lalz-l;tl(-1x12-ca-pnenyi-ammo m-~~=u)Nriz CHz-S(O)z-CH3carboxylic acid o-~uz NHz H Ltiz-Lti(-Ltiz-r-pnenyi-ammo m-~~=u~Nriz CHz-S(O)z-CH3carboxylic acid o-~u2-Ntiz m ai2 ~:ry-~;riz-~:ri3-pnenyi-ammom-~,~=uyvriz CHz-S(O)z carboxylic acid O-JUz-Nriz H l:rlz-l:ri~-1.;ri2-~ri3 u-pnenyi-ammom-~~=u~Nriz CHz-S(O)z-CH3carboxylic acid o-5uz NHz ri Lrlz-uty-uttz-tsn-u-pnenyi-ammom-~~=u~Nriz CHz-S(O)z carboxylic acid CH, o-SOz-NHz H C;Hz-(:H(-(:Hz-Methyl phenoxy-aceticm-C;(=NH)NHz CHZ S(O)Z acid ester o-SOz NHz H z- z- a y -p enoxyacehcm- z CHZ S(O)z-CHjacid ester o-S~-Nl~ H CHz CH(-CHz-Methyl l.'-phenoxy-m-(:(=NH)NHz acetic CHz-S(O)z-CH3acid ester O-JUz-NHz ti l;tlz lai(-laiz-a Y s-p epoxy- m- z CHz-S(O)z-CH3acetic acid ester o-~uz-Ntiz m aiz-gay-~tiz-a Y 3 -p epoxy- m- z CHz-S(O)z-CH,acetic acid ester o- z- z z- z- a iy n- -p epoxym- z CHz-S(O)z-CHjacetic acid ester o-SUz-NHz H (:Hz-C;H(-(:Hz-Methyl Yhenoxyaceticm-(:(=U)NHz CHz-S(O)z-CHjacid ester o-SUz-NHz H C:Hz-C;H(-(:Hz-Methyl (:1-phenoxyacehcm-(:(=U)NHz CHz-S(O)z-CH3acid ester O-JVZ-ivriz ri t,riz-~;ri(-~riz-memyi r-pnenoxyacencm-~~=u~ivtiz CHz-S(O)z-CH3acid ester O-JUz-wriz ri ~riz-Sri(-~riz-Memyi ~ri3-pnenoxy-m-~~=u~wriz CHz-S(O)z-CH3acetic acid ester O-JUz-Nriz z- z- a y 3- -p epoxy m- z CHZ S(O)z-CH3acetic acid ester o- r z z- z- a y n- -p epoxy m- z CHz-S(O)Z acetic acid ester o-SUz-NHz H C:Hz-C:H(-C;Hz-Yhenoxyacehc m-C;(=NH)NHz acid CHz-S(O)z-CH3 o-SOz-NHz H z- z- -p epoxy-acetic m- z aci CHz-S(0)z-CH3 o-SOz-NHz H z- z- -p epoxy- aceticm- z aci CHz-S(O)z-CH3, o-SOz-NHz H C:Hz-C;H(-(:Hz-(:H3-phenoxy-aceticm- z acid CHZ S(O)Z
o-SOz-NHz H C;Hz-(:H(-CHz-C;H3-U-phenoxy-aceticm-(:(=NH)NHz CHz-S(O)z-CH,acid o-SOz-NHz H C:Hz-(:H(-(:Hz13n-U-phenoxy m-(:(=NH)NHz acetic acid CHz-S(O)z-CH3 o-SOz-NHz H (:Hz (:H(-C;Hz-Yhenoxyacehc m-(:(=U)NHz acid CHz-S(O)z o-SOz-NHz H (:Hz C;H(-C;Hz-C;1-phenoxyacehcm-(:(=U)NHz acid CHz-S(O)z-CH3 o-SOz-NHz H z z- -p enoxyacehc m- z aci CHz-S(O)Z
o-SOz-NHz H r z- 3-p epoxy-aceticm- z aci CHz-S(O)z-CH3 o-SOz-NHz H r z- s- -p epoxy aceticm- z CHz-S(O)z-CH3acid o-SOz-NHz H CHz-C;H(-(:Hz-Bn-U-phenoxy m-(:(=U)NHz acetic acid CHz-S(O)z-CH3 o-JUz-lVtiz z- z- enoxye o m- z CHz-S(O)z-CH3 O-JUz-lVriz z- z- -p epoxy-a ano m- z CHz-S(O)z-CH3, O-~uz-Nriz t-~ Ltizwayuay-r-pnenoxy- etnanoim-~~=mryvriz CHz-S(O)z-CHj O-~Vz-lVriz t-~ Ltizwayuaiz-~-ri3-pnenoxy-emanoim- z CHz-S(O)z-CH, o-~uz-Ntiz tt Ltiz-~ti(-~tiz-~ri3-u-pnenoxy-emanoim-~~=wrywriz CHz-S(O)z-CH3 o-~uz-lrtiz r~ ~ni ~nl-~ri~rsn-u-pnenoxy m-~~=wtiyvriz emanoi CHz-S(O)Z
CHj O-~Vz-NHz ti Ltiz-cay-~riz-rnenoxyemanoi m-~~=u~wriz CHz-S(O)z-CH3 O-JVz-Ntlz ri l;riz-l:rl(-l:rlz-~;i-pnenoxyemanoim-~~=vyvriz CHz-S(O)z-CH3 O-JVz-Nriz ri ~riz-qty-~riz-r-pnenoxy-emanoim-~~=uyvriz CHz-S(O)z-CH3 O-JVZ-Ntlz h lalz-l:rl(-1;t12-~ri3-pnenoxy-emanoim-~~=u~rrriz CHz-S(O)z-CH3 O-JUz-wtiz r~ ~tiz-~;ty-~riz-~:ri3-u-pnenoxy-m-~;~=uyvriz emanoi CHz-S(O)z-CH3 o- z- z z- z- n- -p epoxy- m- z a ano CHz-S(O)z-CH3 o-- z H CHZ- z- a y phenoxy-a m_ w aa wad-w,.m y mr~ ma~mu m am au i m CHz-S(O)z-CH3ether o-SUz Hz H C;Hz-(:H(-C:Hz-Methyl (:1-phenoxyethylm-(:(=NH)NHz N
CHz-S(O)i ether o-~uz-Nriz ~riz-~ty-~tiz-iviemyi r-pnenoxy-emyim-Ll=~ti)Nriz CHz-S(O)z-CH,ether o-~u2 riz m ;riz-aril-~;tiz-ivietnyi ~ri3-pnenoxy-m-~:l=~ryvriz N
CHz-S(O)z-CH,ethyl ether O-JUz-lVtiz r1 l:riy-l:ril-1x12-ivietnyi ~ri3-u-pnenoxy-m-~l=Nrywtiz CHz S(O)z-CH3ethyl ether o-~u2 riz n ~riz-aril-~riz-ivietnyi rsn-v-pnenoxym-~l=rVryr~riz N
CHz-S(O)z-CH3ethyl ether O-JVZ-wtiz ri ~;riz ~:ril-~:riz-iviemyi rnenoxyemyim-~;l=u~r~riz CHz-S(O)Z ether o-~u2 tiz ti ~riz aril-~riz-ivietnyi m-pnenoxyemyim-~l=u~~riz lV
CHz-S(O)z-CH3ether O-JVz-Nriz ri ~riz ~;ril-~:riz-iviemyi r-pnenoxyewyim-~:l=u~wriz CHz-S(O)z-CH3ether o-~UZ-Ntiz 2- z- a y ~- m- z CHz-S(O)z-CH3phenoxyethyl ether o-~uz-ivtiz tm aiz pail-~;riz-iviemyi ~ti3-u- m-~;l=u~r~riz CHz-S(O)2 phenoxyethyl CH3 ether o-z- z r r a Y n- m- z CHz-S(O)z-CHjphenoxyethyl ether o-5Vz-Nriz rm :riz-pail-~aiz-pnenyi m-~l=mriyvriz hexane)-o-5Vz-Nriz ti z- z- -p eny m- z hexane)-O-5Vz-NHZ H laiz-fail-l;riz__p eny m-hexane)-O-JVz-NHz ti l:ti2l;ril-1:ri2-lal3-phenyl ~ m-hexane)-O-JUz-Nriz ri ~ri2 aril-~riz-~;ti3-u-pnenyi m- z hexane)-o-JUz-Nr12 tl CaizW ailWriri-v-phenyl m- z air hexane)-o-~u2 tiz tm ;tiz-~;til-~;riz-pnenyi ~ m- z iv hexane)-O-JVz HZ ri l:riz-fail-l;riz-l:l-phenyl m-N
hexane)-O-JVZ-NHZ H l:riz fall-C;riz--p eriy m-hexane)-O-JUz-NHz H Calz-C:ril-(:riq-3-p eriy m- z hexane)-O-JUZ-Nriz ti ~ z- ,- -p eny m- z hexane)-O-SVZ-Nriz H caiz t,til-caiz-tsn-u-pnenyi m-~l=v~~riz hexane)-o-~VZ HZ tl z- z- n1 me p- z N
hexane)-O-JUZ-Ntiz ti laiz-fall-l:rlz-l:l-anllme p-l:l=lVri)lVrlz hexane)-o-~Uz-Nriz W aiz-fail-~:riz-r-amtme ' p- z hexane)-O-JUz t12 ri lalz-l:ril-l;tiz-1x13-arillllle p-l;l=1Vri)lVrtz N
hexane)-O-JUz-iVtlz ti laiz fail-(_atz-(a13-u-anllme p-tJl=irrl)tvrl2 hexane)-o-~uz-lutiz r1 ~riz-aril-~riz-rsn-v-amime p- z hexane)-O-JVz-Ntiz ti l;tiz-C:ril-laiz-Alllllrie p-l.l=V)lVri2 hexane)-o- z- z z- z- -am me p- z ,.~ ~~.,~~
hexane)-O-JUZ-Nriz ri ~;riz-aril-t,riz-r-anume p-~l=u~wriz hexane)-O-JVz-IVHZ ri l.tlz-l.tll-l,tlz-~:H3-amune p-~;l=uyvriz hexane)-o-~uz-NHz m aiz-~;ril-t,riz-~:H3-u-amime p-t,l=uyvriz hexane)-o-~uz-NHZ rm aiz-~:ril-t,riz-tsn-u-amime p-~l=a yvriz hexane)-o-auz NHz ri ~HZ-~ry-~rtz-rnenyi-ammo-carnoxyncm-~l=NH~Nriz hexane)- acid o-JVz lVHZ H l;rlz-l:Hl-l;HZ-l;l-Yneriyl-ammom-l:l=1Vri)lVrlz hexane)- carboxylic acid O-JVz NHZ H l:HZ-l:Hl-l:HZ-r-pnenyl-ammo m-l.:l=lVr1)lVrlz hexane)- carboxylic acid O-JUz-NHz ri ~riz-aril-~riz-~Hj-pnenyi-ammo m-~l=NHJNriz hexane)- carboxylic acid o-au2 NHz H ~HZ-~Hl-~HZ-~H3-u-pnenyi m-~l=NriJwriz ammo hexane)- carboxylic acid o-~uz NHz H ~riz-~Hl-MHz-~sn-u-pnenyi m-~l=NryNriz ammo hexane)- carboxylic acid o-~uz-NHZ H ~:rirt-ty-~HZ-rnenyi-ammo carooxyncm- z hexane)- acid O-JVz-NHz ri ~riz-aril-~riz-~a-pnenyi-ammo m- z hexane)- carboxylic acid o-~uz NHz H LHz-~:Hl-~:HZ_-p eny -ammo m- z hexane)- carboxylic acid o-~uz NHz H Ltiz-tJHI-~:HZ-j-p eny -ammo m- z hexane)- carboxylic acid O-JVz-NHz H C:Hz-l:Hl-l;Hz1;H3-V-prieriyl-ammom-l:l=V)lVrlz hexane)- carboxylic acid o-JVz-NHz H C:HZ C;HI-(:Hz-t5ri-V-prieriyl-alrilll0m- z hexane)- carboxylic acid o- 02-NHz H CHz-CH(-CHz-Methyl phenoxy-aceticm- z hexane)- acid ester o-SOz-NHz H CHz CH(-CHz-Methyl Cl-phenoxyacehcm-(:(=NH)NHz hexane)- acid ester z- z z- z- a y -p epoxy- m- z aceric hexane)- acid ester o-~u2 NHz H ~HZ-~Hl-~HZ-nnemyi ~H3-pnenoxy-m- z hexane)- acetic acid ester O-JUz-NHZ ri ~;riz-aril-~riz-nnemym,H3 u-pnenoxy-m-~l=ivHyvriz hexane)- acetic acid ester O-JVz-Nriz H LHz ~Hl-~HZ-enemy tsn-u-pnenoxym-~l=NH~Nriz hexane)- acetic acid ester o-SUz-NHz H CHz-CH(-CHz-Methyl Yhenoxyacehcm- z hexane)- acid ester o-SOz-NHz H CHz-CH(-CHz-Methyl C1-phenoxyacehcm- z hexane)- acid ester o-SOz-NHz z- z- a y -p enoxyacericm- z hexane)- acid ester o- z- z z- z- a y 3-p epoxy- m- z hexane)- acetic acid ester o-~uz-NHz H MHz ~Hl-~ry-enemy ~ri3-u-pnenoxym-~l=uyvriz hexane)- acetic acid ester o-~uz ut-iz z- z- a y n- -p epoxy m- z hexane)- acetic acid ester o-SUz-NHz H CHZ CH(-CHz-enoxyacehc aci m- z hexane)-o-SOz-NHz H CHz-CH(-CHz--p epoxy-acetic m- z aci hexane)-o- z- z r z- -p enoxy- aceticm- z .~ aci hexane)-o-5Uz-NHz H C:Hz-(:H(-(:Hz-(:Hj-phenoxy-aceticm-(:(=NH)NHz acid hexane)-o-SUz-NHz H C;Hz-C:H(-C;Hz-(:H3-U-phenoxy-aceticm-(:(=NH)NHz hexane)- acid o-5Uz-NHz H C:Hz-(:H(-C;Hz-tan-U-phenoxy m-(:(=NH)NHz acetic acid hexane)-o-SUz-NHz z- r enoxyacehc aci m- z hexane)-o-5Uz-NHz r r -p enoxyacehc m- z aci hexane)-o-SUz-NHz H C;Hz-C:H(-(:Hz-r'-phenoxyacehc m-(:(=U)NHz acid hexane)-o-SOz-NHz H z- r 3-p enoxy-aceticm- z aci hexane)-o-SUz-NHz H C;Hz-(:H(-(:HZ(ai3-U-phenoxy m- z acetic hexane)- acid o-SUz-NHz H (:Hz-(:H(-C;Hz-tan-U-phenoxy m-C:(=U)NHz acetic acid hexane)-o-~uz-mtiz r~ l:riz-aril-laizenoxye ano m- z hexane)-o-~urmtiz ti ~nz-~-ril-1-nz-~-i-pnenoxy-emanoim-l.l=mryvriz hexane)-o-~uz-mtiz t~ ~tiz-uril-uriz-r-pnenoxy- emanoim-l:l=wryvriz hexane)-O-JUz-mHz ri laiz-fail-t~rizl:ri3-pnenoxy-etnanoim-l:l=mryvriz hexane)- -o-~uz-ivriz t~ 2 r 3- -p enoxy-a m- z ano hexane)-o- z- z r z- n- -p enoxy a m- z ano hexane)-o-~Vz-Ntiz tt l:riz t_;ryu:riz-rnenoxyemanoi m-1.1=~yvriz hexane)-o-JUz-NHz z- z- -p enoxye ano m- z hexane)-o- z- , z- r -p enoxy-a ano m- z hexane)-o-5uz-NHz H laiz-fail-Lrizurl3-pnenoxy-emanoim-~l=u~wriz hexane)-o-~uzuvtiz ti Lnz-~-ril-1-nz-3- -p enoxy- m- z a ano hexane)-O-JUZ-NHz ti 1x12-fail-1;t12-ri- -p enOXy- m-a ano hexane)-o-5uz NHz tt Ltiz tail-l:riz-enemy pnenoxy-emyim-l:l=mryvriz hexane)- ether O-~Vz-ivtiz ri l:riz-tail-laiz-nnemyi la-pnenoxyemyim-l:l=mryvriz hexane)- ether o-~uz-lVtlz tl 1,t12-l.rll-1.r12-nnerxiyi r-pnenoxy-emyim- z hexane)- ether o-~uz-ivttz tm _aiz-tail-laiznnemyi l:ri3-pnenoxy-m-l:l=mriyvriz hexane)- ethyl ether o-~uz-ivtiz ti ~tiz-tail-laiz-enemy ~r13-u-pnenoxy-m-l:l=mryvriz hexane)- ethyl ether o-~uz-Ntiz ti l:riz-lay-uriz-Memyi nn-u-pnenoxym-l:l=wrywriz hexane)- ethyl ether O-JUz ivtiz t~ lai2 ~-til-l:riz-enemy rnenoxyetnyim-l:l=uyvriz hexane)- ether o- z- z z- z- a y -p enoxye m- z y hexane)- ether o-~uz-ivtiz tm ;tiz-l:ry-l:rtz-nnemyi r-pnenoxyemyim-l:l=a yvriz hexane)- ether o- ~ H z- z- a m- z U Y
s-hexane)- phenoxyethyl ether o-~uz-Nrlz ti t:rlz-fall-lalz- Mettlyl t~ri3-u-m-l:l=u)Nrlz hexane)- phenoxyethyl ether O-JUZ-Nrlz ri ~riz-aril-~tiz_ ivlemyi tsn_u- m-~l=u~Ntiz hexane)- phenoxyethyl ether O-JUZ-Nrlz ri ~.riz-~:ril-t.riz-pnenyl m-~l=NryNriz (HO-phenyl))-o-~uz-Nriz rl ~riz-aril-~riz-m-pnenyi m-ul=Nn~Nriz (HO-phenyl))-o_JUZ-Nriz ri ~;riz-l:rll_l:rlz_r-pnenyi m-~l=Nti~Nnz (HO-phenyl))-o-~uz-Ntiz r r a-P m- z eny (HO-phenyl))-O_luz-Nri2 H 1x12-fall-l.;riz_l:rig_u-pnenyl m-l:l=Nri)Nri2 (HO-phenyl))-O_JUz_Nri2 z- z- n- m_ z -p eny (HO-phenyl))-O-JU2_Nriz Y z- pnenyl m- z (HO-phenyl))-o-~u2 rlz z- Z -p m- z N eny (HO-phenyl))-o-~uz-Ntiz ti uriz-aril-c:rlz-r-pnenyl m-~l=u~Nriz (HO-phenyl))-O-JUz-Nriz ri t~riz-t,rll_~riz-~:ri,_pnenyi m-l.l=u~lrriz (HO-phenyl))-O-JUz-Nriz ri ~riz-aril-~riz-3_ m- z _p eny (HO-phenyl))-O_JUZ_Nri2 tl uriz-aril-~riz-~n-u-pnenyi m-~l=u~Nriz (HO-phenyl))-O-JUz-Ntiz ti lai2 Call-1x12-Amillle p-l.;l=Ntl)1Vr12 (HO-phenyl))-o-5u2 rlz n tai2 fall-Ltlz-t_;1-aniline p- z N
(HO-phenyl))-o-~ui tiz rl ~-rir~-ril-~riz-r-anume p_l:l=lVr1)lVrlz N
(HO-phenyl))-O-~uz-Nriz ti ~riz-aril-~riz~r13-aniline p-~l=NryNriz (HO-phenyl))-o-~uz tlz tl lalz-~til-~tiz-~r13-u-amlme p- z N
(HO-phenyl))-O-JVz-NHz ti Cain-l~rtl-l:riz-II_ p--anlllle (HO-phenyl))-o-aVz-Ntl2 ti Cain-l:rll-lalz-m p-me (HO-phenyl))-O-JVz-Ntl2 ti C:rlz l:rll-l:rlz_-am p- z me (HO-phenyl))-o-JVz tiz tl z- z- -am p- z N me (HO-phenyl))-o-~Uz-Ntiz tl 1a12-l:rll-~;rtz-~;r13-anllme p-~:l=u)Nrlz (HO-phenyl))-o-5u2 tlz tl Ltlz aril-~tiz-t_;r13-u-aniline p-~l=u~Nriz N
(HO-phenyl))-O-~uz-Nriz ti taiz-~:ril-~tiz-tsn-u-anllme p-~:l=u~Nriz (HO-phenyl))-O_lUz_Ntly ti l.riy_f.rll_1,r12-Ynenyl-amlri0-CarDOXyliC
m-l:l=Nrl)Nriz (HO-phenyl))-acid o-JUz_Ntl2 11 l:riz-l;ril-1:ri2-l:l-Yrieriyi-ammo m-l:l=Nrl)Nrl2 (HO-phenyl))-carboxylic acid o-~uz-Ntlz m :rlz_f,rll-l:rlz-r-pnenyi-amino m-~;l=l~rl~i~rlz (HO-phenyl))-carboxylic acid o-z- z z- z- s-P m- z eny -ammo (HO-phenyl))-carboxylic acid o_ - z H ~2_~ - z- 3_ _p eny~ ammo m- z (HO-phenyl))-carboxylic acid O-JUZ-Nriz ri ~riz-Sri(-~;HZ-tsn-u-pnenYi m-~~=r~HJ~ri2 ammo (HO-phenyl))-carboxylic acid o-~uz-Nriz n ~riz-~H~-~riz-rnenyi-ammo caruoxyncm-~~=u~NHz (HO-phenyl))-acid o-JUz-NHZ ri ~riz-~ri~-~:riz-m-pnenyi-ammo m-~~=uJNHz (HO-phenyl))-carboxylic acid o-JUZ-NHZ ri ~riz-Sri(-~:riz-r-pnenyi-ammo m-~~=u~wHz (HO-phenyl))-carboxylic acid O-JUZ-~riz ri ~:riz-t,ri(-~:riz-~ri3-pnenyi-ammom-~~=uJ~Hz (HO-phenyl))-carboxylic acid o-auz-~riz m :riz-~.ry-~;riz-~,ri3-u-pnenyi-ammom-~.~=u~r~riz (HO-phenyl))-carboxylic acid O-JUZ ~riz ri ~:ri2 Sri(-~;riz-tsn-u-pneny-ammom-~.~=u~mriz (HO-phenyl))-carboxylic acid o-SUz-NHz H CHZ CH(-CHz-Methyl phenoxy-aceticm-C(=NH)NHz (HO-phenyl))-acid ester o-SUz-NHz H CHz-CH(-CHz-a y -p enoxyacehcm- z (HO-phenyl))-acid ester o-SOz-NHz H CHz-CH(-CHz-a y -p enoxy- m- z acetic (HO-phenyl))-acid ester o-JVz-Nriz H z- z- a Y a-P enoxy- m- z (HO-phenyl))-acetic acid ester O-5U2-NHZ H l:H2l:H(-1;H2-MettlYllalg-u-pneriOXY-m-l;(=lVt1)lVriz (HO-phenyl))-acetic acid ester O-JUZ-Nriz H gay-~:Hl-c:Hz-Mertiyi tsn-u-pnenoxym- z (HO-phenyl))-acetic acid ester o-S~NHz H CHz-CH(-CHz-Methyl Yhenoxyacehcm-(HO-phenyl))-acid ester ~Oz-NHz H CHz-CH(-CHz-Methyl (:1-phenoxyacehcm- z (HO-phenyl))-acid ester o-SOz-NHz H CHZ CH(-CHz-Methyl r-phenoxyacehcm-C(=U)NHz (HO-phenyl))-acid ester O-JUZ-NH2 H ~;tiz-~;H(-~:HZ-metnym;ti3-pnenoxy-m- z (HO-phenyl))-acetic acid ester O-JUZ-NHz H ~tiz-~Hl-~HZ-Memy ~ri3-u-pnenoxym-~~=u~mriz (HO-phenyl))-acetic acid ester o-~uz-NHz H ~ry-~ry-~riz-enemy tsn-u-pnenoxym-~~=u~wri2 (HO-phenyl))-acetic acid ester o-SOz-NHz H CHZ CH(-CHz-Yhenoxyaceric m- z acid (HO-phenyl))-o-SOz-NHz H CHZ CH(-CHz--p enoxy-acetic m- z aci (HO-phenyl))-o- z-NHz H CHZ CH(-CHz-J~-phenoxy- aceticm- z acid (HO-phenyl))-o- z-~ r z- 3 p enoxy-aceticm- z aci (HO-phenyl))-z- z- 3- -p enoxy-aceticm- z o- z- z (HO-phenyl))-acid off- Oi-NHz H CHZ-CH(-CHz-Bn-U-phenoxY m-C;(=NH)NHz acetic acid (HO-phenyl))-0~0~ NHz H CHz-CH(-CHz-enoxyacehc aci m- z (HO-phenyl))-o-SOZ-NHz H CHz-CH(-CHz--p enoxyacehc m- z aci (HO-phenyl))-o-~ H CHz-CH(-CHz-F-phenoxyacehc m-C(=U)NHz acid (HO-phenyl))-o-SOi NHz H CHz-CH(-CHz-CH3-phenoxy-aceticm-C(=U)NHz acid (HO-phenyl))-o-SOz NHz H CHz-CH(-CHz-CH3-U-phenoxy m-C(=U)NHz acetic (HO-phenyl))-acid z- z H z- z- n- m- )NH2 -p enoXy acehc acid (HO-phenyl))-O-JUZ-Nriz ri l:riz-l:ril-laiz-rnenoxyemanoi m-l:l=wri)wriz (HO-phenyl))-O-JVz-NHz ~riz-~ry-LHzla-pnenoxy-emanoi m- z (HO-phenyl))-O-JVz-Nri2 ti laiz-l:ril-l:Hz-r-pnenoxy- m-l:l=Nri)Nriz etnanoi (HO-phenyl))-O-JVZ-Ntlz H l:Hz-l:ril-l:Hz-c:ri3-pnenoxy-emanoi m-l:l=Nri)Nriz (HO-phenyl))-O-JU2-Nriz H z- z- s- m- z -P
enoxy-a ano (HO-phenyl))-o-~uz-Ntiz ri l:riz-~ril-~-nz-~sn-u-pnenoxy m-l:l=wri)wriz emanoi (HO-phenyl))-O-JVz-Nriz ri ~-nz-~-nl-un2-rnenoxyemanoi m-l:l=u)wriz (HO-phenyl))-o-~uz-Nriz ri l:riz-lail-laiz-~i-pnenoxyeuianoi m-l:l=u)ivriz (HO-phenyl))-O-JUz-NHz H 1:ri2-l;Hl-l:tlz-r-pneriOXy-eLrianol m-l:l=V)Nri2 (HO-phenyl))-o-~u2 t12 ti 1x12-l;til-1x12-lai3-pnenoxy-emanoi m-1.1=u)ivriz N
(HO-phenyl))-O-JVZ-Nriy H l:rlz l.;ril-1:ri2-1;r13 m-V-pnenOXy-emari0l (HO-phenyl))-O-JUZ-NHZ H l:Hz-l:ril-l:Hz-t5ri-u-prienOXy- m-l:l=u)wriz emanoi (HO-phenyl))-o-JUZ-Nri2 H laiz-lail-laiz-a m- z Y
P
enoxy-a y (HO-phenyl))-ether O-JUz-NHZ . z- z- a m- z y -p enoxye y (HO-phenyl))-ether o-SOz Hz H CHz-CH(-C;Hz-Methyl m-CL(=NH)NHz N r'-phenoxy-ethyl (HO-phenyl))-ether o-5u2 Hz H l~tlz-loll-~;ti2lvlemy11:r13-pnenoxy- m- z N
(HO-phenyl))-ethyl ether o-~u2 Hz H l~tiz-fall-l;tlz-Mell1y11x13-v-prieriOXy- m-N
(HO-phenyl))-ethyl ether O-5Vz-NHz H C:HZ-l.Hl-l.Hz-lVleTllyl m-l.l=lVt1)1Vr12 tan-V-pnenOXy (HO-phenyl))-ethyl ether o-~u2 Hz H l:Hz-l:Hl-~riz-enemy m-l:l=u)mriz N rnenoxyemy (HO-phenyl))-ether O-JVz-NHZ H laiz-fail-l:riz-Merry m-l.l=v)ivriz 1:i-pnenoxyemyi (HO-phenyl))-ether O-~Uz-NHz H l:Hz-llril-l:riz-Meyu m-l.l=v)wriz r-pnenoxyemy (HO-phenyl))-ether o-~uz-NHz r~ laiz-fail-trti2nnemymai3_. m-l.l=u)wriz (HO-phenyl))- phenoxyethyl ether O-JUZ-NHz tl laiz-l.rll-1.r12-l VleLllyll.rlg-u-m-l:l=V)lVrlz (HO-phenyl))- phenoxyethyl ether o-JUz Hz ri l:riz-urll-l:riz- nnecnyi nn-v- m-l:l=v)wriz N
(HO-phenyl))-phenoxyethyl ether O-JVz-NHz H lal2-l:rll-l.;tlz-pnenyl m-l:l=Nrl)Nrlz (Cl-phenyl))-O-JU2 riz ri l:riz-l:ril-~riz-la-pnenyi m- z N
(Cl-phenyl))-o-z z z- z- -p m- z eny (Cl-phenyl))-o-~uz-Nriz ti l:riz-l:ril-~;tlzl:ri3-pnenyi m-l:l=wri)ivriz (Cl-phenyl))-O-JVZ-Ntl2 ti Lriz-Lril-Lriz-Lri3-V-Pnenyl m-l.l=LVri)lVriz (Cl-phenyl))-O-JUz-Nriz ti z z- n- m- z -p eny (Cl-phenyl))-= 127 -H ? z- p ieny m- z o- z- z (Cl-phenyl))-O-JUZ-Nriz ri ~,riz ~:ril-~:riz-~a-pnenyi m-~:l=u)Nriz (Cl-phenyl))-o-JVZ-Nriz ~riz-aril-~HZ-r-pnenyi m-~l=u)NHz (Cl-phenyl))-O-JVZ-Nriz ri ~;riz-~:ril-tlriz-~ri3-pnenyi m-~l=u)Nriz (Cl-phenyl))-o-~uz-NHZ H ~HZ-aril-~riz-~H3-u-pnenyi m- z (Cl-phenyl))-o-'uz-NHz rm ;tiz-~;Hl-~;Hztsn-u-pnenyi m-~:l=u)NHz (Cl-phenyl))-O-JUz-Nriz ri ~:riz-t,Hl-t.riz-Amime p- z (Cl-phenyl))-o-~uz-NHZ n ~riz-~Hl-~HZ-m-amime p- z (Cl-phenyl))-o-~uz-NHZ n ~riz-aril-~HZ-r-amime p- z (Cl-phenyl))-O-JUZ-NHz H l;Hz-l:Hl-1:H2-1:H3-anlllIle p- z (Cl-phenyl))-O-JUZ-NH2 ti l.rlz-lail-l:HZ-lalg-u-anllllle p-1.1=lVr1)lVriz (Cl-phenyl))-o-~uz-NHz H ~riz ~Hl-~rizrsn-u-amime p- z (Cl-phenyl))-O-JUZ NHz H 1;t12-loll-1x12-ATllllIle p-1.1=U)lVriz (Cl-phenyl))-o-~Vz-NHz H l:HZ-~:Hl-laiz~:1-anlllne p- z (Cl-phenyl))-o-~uz-NHz H LHZ LHl-MHz-r-amime p-~l=u)Nriz (Cl-phenyl))-O-JUy-NHz H l:riz l;Hl-lalz-3-am me p-(Cl-phenyl))-o-SUz-NHZ H z z- 3- -am me p- z (Cl-phenyl))-o-JUZ-NHz H l:Hz-l:Hl-t_;HZ-tSn-U-amlme p-Ll=u)lVriz (Cl-phenyl))-O-JUz-NHy H 2- z- eriy -amlll0-carm- z Oxy lc (Cl-phenyl))-acid o-1U2-NHz H l.Hz C.HI-l;Hz-l.l-Ynenyl-amln0m-l.;l=1VH)lVrlz (Cl-phenyl))-carboxylic acid o-5Uz-NHz H l:Hz C:HI-t;Hz-r-pnenyl-ammo m- z (Cl-phenyl))-carboxylic acid O-~Uz-NHz H LHz LHl-MHz-~H3-pnenyi-ammo m- z (Cl-phenyl))-carboxylic acid o-5Uz-NHz H ~;Hz LHl-t;HZ-~:H3-u-pnenyl m-~l=~H)~riz ammo (Cl-phenyl))-carboxylic acid O-JUZ-NHz H l.Hz C.,HI-l~Hz-tin-U-pnenyl m-l:l=lVr1)lVtlz ammo (Cl-phenyl))-carboxylic acid O-JUZ-NHz H 1;H2-(:Hl-l.;HZ-Yneriyl-amino m- z CarUOXyIIC
(Cl-phenyl))-acid O-~Vz-NHz H caiz ~Hl-LHZ-~1-pnenyi-ammo m-~l=v)Nriz (Cl-phenyl))-carboxylic acid o-~uz-NHz H ~HZ-~Hl-~rizr-pnenyi-ammo m-~l=~)mriz (Cl-phenyl))-carboxylic acid o-5uz NHz H MHz-~Hl-MHz-~H,-pnenyi-ammo m-~l=~)mriz (Cl-phenyl))-carboxylic acid o-5uz NHz H ~Hz-~Hl-c:Hz-uH3-u-pneny-ammom-~l=u)~r~z (Cl-phenyl))-carboxylic acid o-JUz-NHz H C.:Hz-l;Hl-1;H2-tin-u-pneriyl-ammom-l;l=v)i~riz (Cl-phenyl))-carboxylic acid o- z- a - H r z- a y p enoxy-acericm- z (Cl-phenyl))-acid ester z- z H z- r a y -phenoxyaceric W W i ~m .~ my~aa m- z (Cl-phenyl))-acid ester o-SUz NHz H CHz-CH(-CHz-Methyl F-phenoxy-m-C(=NH)NHz acetic (Cl-phenyl))-acid ester o-~uz-rVriz ri ~riz-pail-t.;tiz-Memyi t_;ti3-pnenoxy-m-~:l=mryNtiz (Cl-phenyl))-acetic acid ester O-JUZ-rVriz ri ~:riz t.ril-~:riz-Memyi ~ri3-u-pnenoxy-m-~l=rrryNriz (Cl-phenyl))-acetic acid ester o-~uz-rVriz ri ~riz-aril-~riz-Memyi ~n-u-pnenoxym-~l=NryNtiz (Cl-phenyl))-acetic acid ester o-SUz-NHz H CHz-CH(-CHz-Methyl Yhenoxyacehcm-(:(=U)NHz (Cl-phenyl))-acid ester o-SOz-NHz z- z- a Y -p enoxyaceticm- =U z (Cl-phenyl))-acid ester o-SOz NHz H CHz-CH(-CHz-a y -p enoxyacehcm- z (Cl-phenyl))-acid ester o-~uz-tvtiz z- z- a y ,-p enoxy- m- z (Cl-phenyl))-acetic acid ester o-SOz-NHz z- z- et Y a- -p epoxym- z (Cl-phenyl))-acetic acid ester O-JUz-Ntiz r~ ~riz-aril-~riz-Merry rsn-u-pnenoxym-~l=u~r~riz (Cl-phenyl))-acetic acid ester o-SOz-NHz H CHz-CH(-CHz-Phenoxyacehc m- z acid (Cl-phenyl))-o- Uz=NHZ H z z- -p epoxy-acetic m- z -- aci (Cl-phenyl))-o-SOz-NHz H CHz CH(-CHz--p epoxy- aceticm- z aci (Cl-phenyl))-o-SOz-NHz H CHz-CH(-CHz-CH3-phenoxy-aceticm- z acid (Cl-phenyl))-o-~Oz-N~ H CHz-CH(-CHzCH3-U-phenoxy-aceticm-C(=NH)NHz (Cl-phenyl))-acid o-SUz NHz H CHz-CH(-CHz-tin-U-phenoxy m-C(=NH)NHz acetic acid (Cl-phenyl))-o-SOz-NHz H CHz CH(-CHz-Yhenoxyacetlc m-(:(=U)NHz acid (Cl-phenyl))-o-SOz-NHz H CHz-CH(-CHz-Cl-phenoxyaceticm- z acid (Cl-phenyl))-o-SUz NHz H CHz-CH(-CHz-F-phenoxyacetlc m- z acid (Cl-phenyl))-o-SOz=NHz H CHz-CH(-CHz-3-p epoxy-aceticm- z aci (Cl-phenyl))-o-SOz-NHz H CHz CH(-CHz-3- -p epoxy aceticm- z (Cl-phenyl))-acid o-SOz-NHz H CHz CH(-CHz-n- -p epoxy aceticm- z aci (Cl-phenyl))-O-JUz-Nriz n ~:riz-Lnl-~riz-enoxye ano m- z (Cl-phenyl))-o-~uz-Nriz r~ ~tiz ~rtl-~riz--p epoxy-a ano m- z (Cl-phenyl))-o-~uz rvtiz rm aiz-~:ry-~;riz-r-pnenoxy- emanoim-~;l=mry~riz (Cl-phenyl))-O-JVZ-Nriz ti lalz-l:ril-(:riz-1:ri3-prieriOXy-elllanolm-l;l=iVrl)lVrlz (Cl-phenyl))-O-JVZ-lVriz ti laiz-l:rll-laiz-l:rlg-u-pnenOXy-eirian0lm-l;l=lVr1)1Vr12 (Cl-phenyl))-o-~uz Ntiz t~ Lnr~-ril-~riz-~sn-u-pnenoxy m-~;l=r~ryvriz emanoi (Cl-phenyl))-o-~uz-Ntiz r~ ~nz-~nl-~nz-rnenoxyemanoi m-~l=u~mriz (Cl-phenyl))-o-~uz-Ntiz ti ~tiz-aril-~-tiz~a-pnenoxyemanoim-t.l=a ~r~riz (Cl-phenyl))--o- H z- z ~-p m- z V V 11 enoxy-et 1 z ano z-(Cl-phenyl))-o-JUZ-Nriz ri ~:riz-~:ril-~;tiz-~H3-pnenoxy-emanoi m-~l=u)NHz (Cl-phenyl))-O-JUZ-Nriz ti l.tlz t,Hlw;ty-LH~-u-Pnenoxy- m-~;l=u)NHz emanoi (Cl-phenyl))-o-~uz-NHZ rm a~z-~:Hl-~:H2nn-u-pnenoxy- m-Ll=u)NHz etnanoi (Cl-phenyl))-o-~uz riz n ~riz-aril-urizenemy m-~l=NH)Nriz N pnenoxy-emy (Cl-phenyl))-ether o-auz HZ rm ;riz-~:ril-~:riz-Memyma-pnenoxyemyi m-~;l=~ri)wHz N
(Cl-phenyl))-ether o-JUz tiz rm ;rizw:Hlw;HZ-nnemyi m-~;l=r~ri)NHz N r-pnenoxy-emyi (Cl-phenyl))-ether O-JUz-NHZ ri ~riz-aril-~riz-nnetnym;H3-pnenoxy- m-~:l=NH)Nriz (Cl-phenyl))-ethyl ether o-JUz-NHZ ri ~;riz-aril-~riz-nnemyi m-~l=NH)NHz ~ri3-u-pnenoxy-(Cl-phenyl))-ethyl ether o-~uz-NHz z- z- a m- z y n--p enoxy (Cl-phenyl))-ethyl ether o-~uz-NHZ H ~riZ ~Hl-~HZ-Mewyi m-~l=u)r~Hz rnenoxyemyi (Cl-phenyl))-ether O-JUz-Ntiz ri uriz aril-~riz-Meyu m-~l=u)r~riz m-pnenoxyemy (Cl-phenyl))-ether o-~uz-NHz H ~:HZ-~:Hl-MHz-a m- z y -p enoxye y (Cl-phenyl))-ether o-JUZ-NHz z- z- a m- z y ~
(Cl-phenyl))- phenoxyethyl ether o-JUz-NHz H l;Hz l;til-(:Hz- nnetnym:ri,-u-m-~l=u)~riz (Cl-phenyl))- phenoxyethyl ether o-SOz-NHz H CHz-CH(-CHz- Methyllin-U- m- z (Cl-phenyl))-phenoxyethyl ether O-JUz-NHz t1 l;HZ-~:Hl-l:Hz-p m-eny , ~z)-O-JVz-NHZ H l:HZ-l:Hl-l:HZ-l:l-pnenyl m-l:l=lVri)lVriz ~z)_ O-JVy-NHZ t~ c:riz-aril-uHZ-r-pnenyi m-~:l=~ri)wriz ~z)_ o-'uz-NHZ H trHz ~Hl-~:riz-t.H3-pnenyi m- z ~z)-o-~uz-Ntiz n ~riz-pail-~:riy:ri3-u-pnenyi m- z ~z)-O-JUz-Nriz H ~riz-aril-~riz-rsn-u-pnenyi m-~l=Nri)rVriz ~z)-O-JVz HZ H ~riz-~:ril-~:HZ-pnenyi m-~;l=u)~riz N
~z)-O-JUz HZ H ~:riz-t,ril-~:riz--p m- z N eny NHz)-O-JUz-NHz H l:HZ-l:Hl-1;H2__p m_ eriy .
~z)_ o-z- z z- z- 3-P m- z enY
~2)-o-z- z z' z- 3 m- z -P
enY
~z)--- -o-z-~2 ~z ~(_CHz-Bn=O_phenyl m_C(=O)NHz ~z)-O-lUZ-lVHZ r1 z- z- m p- z me ~z)-O-JUZ-Nriz ri ~riz t.Hl-~riz-~;i-amime p-~l=NH)Nriz ~z)_ O-wz-NHZ ri ~ri2 ~Hl-~HZ-r-amime p-~l=Nri)Nriz ~z)-z- z- j-am me r,w iai m .~ ma ay.ra o- z- z p-~2)-o-50z-~Hz H CHz-CH - 3- -aniline p-C(=NH)NHz z-~z)-o-JU2 lVtiz r z- n- -am me p- z ~z)-o- z- z H CHz CH(=CHz-~I~e p-C(=O)NHz ~z)-O-JUz-wriz ri l:riz-~:ri(-l:riz-la-amime p-~.~=u)r~riz ~z)-o-~uz-tvtiz tt z- z- -am me p- z NHz)_ o- z- z CHz-CH(=CHz=-CH3-aniline p-C(=O)NHz ~z)-O-JVZ-Ntiz ti 1x12-lal(-lain-l.aig-V-anllme p-l:(=u)iVti2 ~2)-o-~uz-lvriz ti laiz-l:ry-l:riz-rsn-u-amime p-~;~=u)rVtiz ~z)-o-~uz-Ntiz ti lai2l:ry-laiz-rnenyi-ammo-carooxyncm-1.~=trti)rrtiz NHz)- acid o-JVZ-Ntlz n 1:ri2-l;ri(-1:ri2-l:l-Yneriyl-ammom-l,(=1Vri)1Vt12 NHz)- carboxylic acid o-~uz-Ntiz ti laiz-l:ry-l:riz-r-pnenyi-ammo m-1:~=rVri)Nriz NHz)- carboxylic acid O-JUz-NHZ t1 1:ri2-lal(-l:riz-1x13-pnenyl-ammom-l:(=lVr1)1Vt12 NHz)- carboxylic acid O-JVZ-NHZ H 1x12-lal(-lalzl:rig-u-prienyl m-1:~=lVt1)lVth ammo NHz)- carboxylic acid O-JUz-Nriz tt Lriz Lril-Lriz'~n-V-pneny ammo m- z NHz)- carboxylic acid O-~uz-Ntiz ti 2 z- eny -ammo car m- z oxy is NHz)- acid o-~Vz-Ntlz z- z -p eny -ammo m- z NHz)- carboxylic acid o- z- z z- z- -p eny -ammo - m=C( ~)NHz -..
NHz)- carboxylic acid o- z- z r r 3-p eny -amino -m-C
-~.aa a i NHz)- carboxylic acid o- r z z- z- 3- -p eny -aminom- ~ ~)~z - v Ul1 V a 1 NHz)- carboxylic acid o- z- z z- z- m-C(=O)NHz ~. ..
n- -p eny -amino NHz)- carboxylic acid o- z- z z- z a y p enoxy-aceticm- )NHz ~.. ~.. . .~ ,_.~ .,..
NHz)- acid ester o- z- z r z- a y -p enoxyacehcm-C(-NH)NHz NHz)- acid ester o-SUz-NHz H CHz CH(-CHz-a y -p enoxy- m- z acetic NHz)- acid ester O-JVz-rrtiz t~ l:riz l:ry-l:riz-Memyi l:ri3 pnenoxy-m-1:~=wri)rrriz NHz)- acetic acid ester o-~uz-Nriz r~ l:riz-l:ry-l;riz-rnemyi l:ri; m-1:~=rVri)rrriz u-pnenoxy-NHz)- acetic acid ester O-JUZ-1Vt12 t1 lalz-lal~-laiz-MeTtlyl tiri-V-pneriOXym-l:(=lVt1)lVriz NHz)- acetic acid ester o-SU2 NHz H CHz-CH(-CHz-Methyl Yhenoxyacehcm-C(=U)NHz NHz)- acid ester o-SUz-NHz H CHz-CH(-CHza y -p enoxyacehcm- z NHz)- acid ester o-SUZ NHz z- z- a y -p enoxyacehcm- z NHz)- acid ester o- z- z z- z- a Y 3-p enoxy- m-NHz)- acetic acid ester o- z- z z- r a 1y s- -p epoxym- z NHz)- acetic acid ester o- z- z z- z- a y n- -p epoxy m- z NHz)- acetic acid ester o-~ H CHz- z- enoxyacehc aci w.u~-w.ai ~~ mu~mu m- z NHz)-o-SUz-NHz H CHz-CH(-CHz-Cl-phenoxy-aceticm-C(=NH)NHz acid NHz)_ o-SUz-NHz H CHz-CH(-CHz-F-phenoxy- aceticm-C(=NH)NHz acid NHz)_ o_ _ z H ~_ ~3_~xy=acetic iiW~ NH)NHz acid ~z)-o- z' z z- r 3- -p epoxy-aceticm- z NHz)- acid o- z- z z- z- n- -p epoxy aceticm-C(=NH)NHz acid ~z)-o- z- z z- z- enoxyacehc aci w.~ vym m-o- r z -p enoxyacetic in-C(=O)NHz ,_,~. ,_,..~-,...acid i z- ,.. ~.
NHz)_ o-SOz-NHz H CHz-CH(-CHz->~-phenoxyacehc m- z acid ~z)-o-SOz-NHz H CHz-CH(-CHz-CH3-phenoxy-aceticm-(:(=U)NHz acid ~z)-o-SOz-NHz H CHz-CH(-CHz-CH3-U-phenoxy m- z acetic NHz)- acid o-SOz-NHz H CHz-CH(-CHz-Bn-U-phenoxy m-C(=U)NHz acetic acid ~z)-O-JUz NHz t1 lalz l;tll-1:112-YrieriOXyeitlan0lm-l;l=lVt1)lVriz NHz)_ O-~Vz-Nri2 t~ c:riz-pail-~aiz-t,i-pnenoxy-emanoim-~:l=mryvriz ~z)_ o-JUy-Nri2 t1 lalz-fall-lalz-r-prienOXy- eirianolm-NHz)_ O-JVy-Ntlz z- z- g-p eriOXy-a m-ari0 ~z)-o-~Vz-Ntiz tt uriz-~ril-~nz-~ri3-~-Pnenoxy-emanoim- z ~z)-O-JUy-lVri2 Y r n- -p epoxy a m- z ano ~2)-o- z- z z- z- enoxye ano m- z NHz)_ O-JVZ-NHZ ri ~ty;ry-~riz--p enoxye ano m- z ~z)-o-JVi NHz z Z- -p epoxy-a ano m-NHz)_ o-aVz-ivtiz z- z- 3-p epoxy-a ano m- z ~2)-o- z- z CH3-U-Phenoxy- m-C(=O)NHz .... ~..~~-~.,~.ethanol r z-~z)-o-~uz-mtiz ti trtiz t_;ril-~riz-isn-u-pnenoxy- m-~l=~yvriz emanoi ~2)-O-JU2-1Vt12 h l.:riz-l:ril-l:riy-Meuryi pnenoxy-emym-~l=wrywriz NHz)- ether o-auz-wriz m ;tizw;ty-~tiz-enemy m-pnenoxyemym-~l=ivryvriz NHz)- ether o-~uz-Nriz ri ~riz-~:ril-~riz-Memy r-pnenoxy-emym-~l=mryvriz NHz)- ether o-~uz-wtiz ri ~riz-aril-~riz-nnewyi ~ri3-pnenoxy-m-~l=wriyvriz NHz)- ethyl ether O-JU2-lVriz ti tatz-~;til-~tiz-enemy ~ri3-u-pnenoxy-m-~:l=mryvriz NHz)- ethyl ether ~
o-z- z r z- et m- z iy n--p enoxy NHz)- ethyl ether o- z- z- a w a as y .~ ma m z enoxye m- =O~ z z- y iva ua a a a ua m NHz)- ether o-z- Z- - CH2= z- a m-C(=O)NIT
. w a H .aa~- v.u y a~ m -phenoxyethyl ava ua m.a NHz)- ether o-~uz-Nnz n t,nz-~;n~-tlnz-nnemyi m-~;~=u~Nnz r-pnenoxyemyi NHz)- ether o-~uz-Nnz n unz-un~-unz nnetnyi m-u~=u~~nz c:n3 NHz)- phenoxyethyl ether o-~uz-Ntiz t-~ unz unz- Memyi m-u~=u~~nz ~n~- ~:ri3-u-NHz)- phenoxyethyl ether o-~uz-~tiz n unz unz- enemy m-~~=~~wnz ~n~- rsn-u-NHz)- phenoxyethyl ether z- z s z P m- z enY
o-z- z s z -P m-~-(=rrn)mnz enY
o-z- z s z -P m- z enY
z- z s z 3- p m_ -~)~Z
eny -o-2 2 3 2 ;- - p eny m_C(=z o-z- z s z n_ eny m- z _p o-z- z s z p mz eny _ o-z- z s z -p m_~-p)~z eny , o-z- z s z -P m- z enY
n-z- 2 3 z j-p m=~z eny _ -o-r 2 3 2 7- p eny m_~-O)~z - -o-z- z s z n_ eny m=C(=O)N~
_p o-z- z s z m P-Cz me z- z s z -a1ll p-me o-z- z s z -am p-C(=NH)NHz me z- z s z 3-am p- z me o-z- z s z ; p- )NHz -am me o-z- z s z n- p- z -am me o-z- z s z m p- z me o-r z 3 z -am p-t.~=a me ~wnz r z s z -am p- z me o-z- z s z 3-am p- )NHz me o-z- z s z 3- p-C(=O)NHz -am me o-r z s z n_ p- z -am me o-z- z s z eny m-C(=NH)NHz -ammo-car oxylic acid O-JUy-Nri2 ~;ti3 z eny m- z -ammo carboxylic acid o-JUq-Nri2 ~;ti3 ~;nz r-pnenyi-ammo m-~.~=mnyvnz carboxylic acid o-JUZ-lVHz 1;t13 l:riz 1.;ri3-pnenyl-ammo m-carboxylic acid o-auz-Nnz ~;ti, trnz 3- m- z -p eny ammo carboxylic acid o-z- z 3 z n- m- z -p eny ammo carboxylic acid o-~uz-wnz uti, unz rnenyi-ammo m- z carooxync acid o-~uz-Nnz Lti3 ~tiz -p m- z eny -ammo CH3carboxylic acid o-JU2-Ntlz Lti, unz r-pnenyi-ammo m-~~=v~rrnz carboxylic acid o-JUZ nz ~:n3 ~atz ~;nj-pnenyi-ammo m-~~=u~mnz N
carboxylic acid o-~uz-Ntiz ~;t13 ~;nz ~n3-u-pnenyi-ammo m-~~=~~mnz carboxylic acid o-z- z s z n- m- z -p eny -ammo car oxyIic acid-o- z- z 3 z et m- z y p epoxy-acetic acid ester o- z- z , z a m- z y -p enoxyacehc acid ester o- z- z 3 z a m- z y -p epoxy-acetic acid ester O-JVz ivriz 3 ~;tiz a m- z y 3-p epoxy-acetic acid ester O-JVz lVriz ~ti3 ~aiz rnemym:rt3-u-pnenoxy- m-~;~=mriyvriz acetic acid ester o-auZ wtiz ~ri3 ~riz nnemyi m-~~=mrywriz ~sn-u-pnenoxy acetic acid ester o-SOZ NHz CH3 CHz Methyl m-C(=U)NHz Yhenoxyacehc acid ester o-SOz-NHz CH3 CHz Methyl m-C(=U)NHz C1-phenoxyacehc acid ester o-SOz-NHz CHj CHz Methyl m-C(=U)NHz >~'-phenoxyacehc acid ester O-JUz-lrtiz ~rij ~riz nnemyi m-~~=vlwriz ~ri3-pnenoxy-acetic acid ester o-JVz NHz 1;t13 ~tiz enemy m-~~=ulwriz Sri;
u-pnenoxy acetic acid ester o-~uz-lVtiz ins ~nz lnemyi m-~t=v~rrriz rsn-u-pnenoxy acetic acid ester o- z- z , z enoxyacehc m- z aci o- z- z 3 z -p m- z epoxy-acetic aci o- z- z s z -p m- PHZ
epoxy- -acetic aci o- 2 2 3 2 ;- p in=~~Nl~jl~Z
epoxy-acetic aci o-SOz-NHz , z 3- m- z -p epoxy-acetic acid o- z- z s z n- m- z -p epoxy acetic aci o- z- z s z enoxyacehc m- z aci o- z- z s z -p m- z enoxyacehc aci o- ~ z , z -p m~(~jN~Z
enoxyacehc aci o- z- z a z 3 m- z p epoxy-acetic aci o- z- z 3 z ;- m- z -p epoxy acetic acid o- z- z s z n- m- z -p epoxy acetic aci o- z- z 3 z enoxye m-~t=wryrrriz ano o- z- z s z -p m- z epoxy-a ano o- r z s z -p m-~:~=mryvriz epoxy-a ano o- z- 2 3 2 ;- p m- z epoxy-a ano o- z- 2 3 2 3- - p epoxy-a uri=C(=NH)NHz ano o- z- z 3 z n- epoxy a m- z -p ano o- z- z s z enoxye m~NHz ano o- z- z 3 z -p m- z enoxye ano o- z- z 3 z -p m-epoxy-a -ano 0- z- 2 3 z g- p m- 2 epoxy-a ano o- z- 2 3 2 ;- - p epoxy- m-a ano -o- z- z s z n- epoxy- a m- )NHz -p ano o- z- z s z ethyl m-C(=NH)NHz pethyl ether o- z- z s z a m- z y -p enoxye y ether o- z- z s z a m- z y -p epoxy-a y ether O-JVZ-Nriy ~ri3 ~riz memyi m- z ~ri3-pnenoxy-ethyl ether o-~uz-lvtiz ~ti3 caiz a m- z y -p epoxy-ethyl ether o-SOz-~I-Iz CH3 z a m- z - y - n--p enoxy ethyl ether O-JUZ-writ t,ri3 ~;tiz lviemyi m-~;(=u)wrtz rnenoxyemyi ether o-r z s z a m- z y -p enoxye y ether o-z- z s z a m- z y -p enoxye y ether o-z- z s z a m- z Y
s-phenoxyethyl ether o-~uz-wtiz s z a m- z Y
phenoxyethyl ether O-JUZ-wriz ~ri3 ~;riz nnemyi m-~(=u)wriz rsn-u-phenoxyethyl ether z- z s z- z P m- z enY
o-z- z s z- z -P m- z ~ enY
0-2 2 3 z-~ 2 -~yi _ o-r z s ~z- z 3- phenyl m_C(=~~z o-2 2 3 2 2 3- - p eny m- z -o-z- z s z- z n_ enyl m=C(-~)~z _p -o-z- z s i z p m-eny _~ _,_._ _ o-z- z a z- z -P m' z enY
o-z- z s r z =phenyl m-C(=O)NFT
o-z- z s z- z s- P m- z enY
--o-z- z s z- z 3- O=phen~ m-C(=O) o-z z a z- z n- eny m- z -p o-z- z s z- z m p- z me o-z- z s i z -am p- NFL
me o-z- z s z- z -am p-C(= z me o-z- z 3 z- z 3-am p- z me o-z- z 3 r z 3- p-C(=NH)NHz -aniline o-z- z 3 z- z n_ p- z _am me o-z- z s r z m p-~(=u)wriz me z- 2 3 2- z -am p- z me -n-r z s z- z -am p- ~~HZ
me z- z s z- z 3-am p- z me o-2 2 3 2- z 3- p-~;(=u)wnz -am me o-z- z 3 z- z n_ p- z _am me o-r z a z- z eny m=C( NH)NHz -ammo-car oxy is acid o-~uz-wtiz ~;rij z- z eny m- z -ammo carboxylic acid o-JVZ-writ t,ri3 Ltiz-~:riz r-pnenyi-ammo m-~(=wri)wriz carboxylic acid o-~uz-wttz ~:ri3 Lriz-~:riz tai3-pnenyi-ammo m-~(=wti)wriz carboxylic acid o-~u2-wriz ~ri3 ~riz-~riz ~ri3-u-pneny m-~(=wri)wriz ammo carboxylic acid o-z- z s z- z n_ m- z _p eny ammo carboxylic acid o-~uz-wriz ~ri3 ~riz-~riz rnenyi-ammo m-~(=u)wriz carnoxync acid o-~u2 riz ~ri3 ~riz-~rlz m-pnenyi-axmno m-~(=u)wriz w carboxylic acid O-JUz riz ~ti3 taiz-~:riz r-pnenyi-ammo m-~:(=u)wriz w carboxylic acid O-JUZ-wriz ~ri3 ~riz-~riz ~ri3-pnenyi-ammo m-~:(=u)wriz carboxylic acid o-~uz-wriz t;ri3 t,riz-~:riz ~ri3-u-pnenyi-ammo m-~(=u)wriz carboxylic acid o-z- 2 3 2- z n-O-pheny m--ammo car oxy is aci o-Oz-z CH3 z- z a m- z iy p epoxy-acetic acid ester o-SUz-NHz 3 CHz-CHz Methyl m-C(=NH)NHz C1-phenoxyacehc acid ester o-z- z 3 CHz Hz Methyl m-C(=NH)NHz C r'-phenoxy-acetic acid ester o-~uz-wriz uri3 uriz-uriz nnemyi m-~(=Nri)Ntiz uri3-pnenoxy-acetic acid ester o-~u2 riz uri3 uriz-uriz Memyi m-u~=Nri)Ntiz w uri3-u-pnenoxy-acetic acid ester O-JUz-wriz , z- z a m- z Y
n--p epoxy acetic acid ester o-~ z s z- z a m- z y enoxyacehc acid ester o-SUz-NHz 3 z- z a m- z y -p enoxyacehc acid ester o-SUz-NHz a z- z a m- z y -p enoxyacehc acid ester o-z- z CH3 CHz-CHz Methyl m-C(=O)NHz CH3-phenoxy-acetic acid ester O-JUz-Ntlz uti3 utiz-~riz enemy m-~~=u)rrriz uri,-u-pnenoxy acetic acid ester o-~u2 tiz ~at3 ~;rtz-~riz nnemyi m-~,~=u)ivriz iv lsn-u-pnenoxY
acetic acid ester o-z- z 3 z- z enoxyacehc m- z aci o-z- z 3 z- z -p m- NFT
epoxy-acetic aci z- 2 3 2 2 -p m-C(= z epoxy-acetic aci o-2 2 3 2- z 3- p m- z epoxy-acetic aci o-z- z s z- z CHa-O-p~erioxy-aceric m-C(=NH)NHz acid o-z- z s z- z n- m- z -p epoxy acetic aci o-z- z a z- z enoxyacehc m- z aci o-z z s z- z Crp m-C(=O)NHz e~cetic acid o-z- z s z- z -p m-C(=O)NHz enoxyacetic acid o-2 2 3 2- z 3- p m- z epoxy-acetic aci o-z- z s z- z j- m-C(=O)NHz -phenoxy acetic--acid o-z- z s z- z n- m- z -p epoxy acetic aci o-z- z s z- z enoxye m- z ano o-z- z s z- z -p m- 2 epoxy-a ano o-z- z s r z -p m-C(=NH)NHz epoxy-a and o-z- z s z- z 3 m- z p epoxy-a ano o-r z a z- z ~n3-u- Pnenoxy-emanoim-~~=mri)mriz o-z- z 3 z- z n- epoxy a m- z -p ano o-z- z s z- z enoxye m- z ano o-z- z s i z -p m-C(=O)NHz enoxyethanol o-r 2 3 2- z -p m- z epoxy-a ano o-z- z s z- z 3-p m- NHz epoxy-a ano o-z- 2 3 2 2 j- p epoxy- m- z - a ano o-2 2 3 2- z n- epoxy-a m- z -p ano o-z- z a z- z a m- riz y p epoxy-a y ether o-~uz-wtiz tJti3 ~tizm:riz nnemym-pnenoxyemy m-~:~=mri)mriz ether o-~uz-ivtiz ~ai3 ~tiz-~riz nnemyi m-~.~=ivri)ivriz r-pnenoxy-emyi ether o-~uz-wriz uri, ~riz-~riz memyi m-u~=ivri)ivriz uri3-pnenoxy-ethyl ether o-~uz-Nriz uri3 ~riz-~riz nnewyi m-ut=wryvriz uri3-u-pnenoxy-ethyl ether o-z- z 3 z- z et m- z y n--p enoxy ethyl ether O-JVZ-lVriz 3 z_ z nnemyi m-c:~=V)wriz rnenoxyemyi ether o_i z s z_ z a m- z y -p enoxye y ether O-JVz-lVriz 3 z- z a m- z y -p enoxye y ether o-~Vz-Nriz l:ri3 l;riz-l:riz enemy m-t,(=V)wriz ~ti3-phenoxyethyl ether O-JVz-lVriz 1:ri3 l:riz-l:riy Melllyll:ri3-V- m-l:(=V)1Vt12 phenoxyethyl ether O_z- 2 3 2_ z a m_ z Y
n_ phenoxyethyl ether o_z- z a z- z-z P m_ z enY
o_2 2 3 2 2_z -p m-eny -.
O_z_ z 3 z- z_z -p m_C~-eny o_z_ z a z_ z-z s_ P m_ z enY
o_r z s z- z-z 3- - p eny m-~;~=~ti)mtiz o_z_ z s z_ z-z n- eny m- z -p - -o-z_ z 3 z- z-z p m-C(=O)~z eny o_z- z s z- z-z _p ~)~z eny O_z- 2 3 z- z-z _p m_C(=O)~z eny --o_z- z s r z-z 3-p m-C(-O)NHz eny o_z- z s z- z-z 3 P enY z _ o_z z s z- z_z n_ eny m- z _p O_z_ z a Y z_z n1 p_ me o_z_ z s z- z-z -am p-~:(=~t~)~tiz me O_z z s z- z-z -am p- z me o_z_ z s z- z z 3-am ~(=NH)NFIz me o_z_ z s z- z-z 3- p- z -am me O-z_ 2 3 z- z-z n_ P_ _am me O_z_ z s z- z z m p_ (=O)~z me O_z- 2 3 2 2_z -~ P_ z me O_z- 2 3 z- z_z -am p- z me o_z- z s z- z-z 3-am p- z me 2_ 2 3 2_ 2_2 3' -anl --.
me 2 2 3 z- z-z n_ p_ z _am me o_z- z s z- z-z eny m-C(=NH)NHz -ammo-car oxy is acid O-JUZ-Ntiz Lti3 laiz tiz-l:rizla-rnenyi-ammo m- z ~
carboxylic acid --o_r z s z_ z-z -P m-C(-NH)NHz enY
-ammo carboxylic acid o-~VZ tiz l;ti3 laiz-laiz-laizl:ri3-pnenyi-ammo m- z tv carboxylic acid O-JUz tlz Lti3 l:riz-l:riz-l:rizl;ri3-V-pnenyi m- z 1v ammo carboxylic acid O-JUz-Ntiz Lri3 ~nz-~ riz-~nz ~sn-V-pnenyi m- z ammo carboxylic acid O-JUz-Nriz 1:ri3 ~-rizWriz_1-riZYrienyl-ammo m-CarDOXyIIC
acid O-JVz-Nriz lai3 l:riz-l;tiz-laizl;i-pnenyi-ammo m- z carboxylic acid O-JVZ-Nriz l;ti3 ~riz-~riz-~-nz r-pnenyi-ammo m-~l=V)r~riz carboxylic acid o-~Vz-lvtlz lat3 l:riz-l:riz-l:rizl;ri3-pnenyi-ammo m-~~=V)~riz carboxylic acid o-JVZ tiz 1x13 1x12-l:riz-l;tlzl;ri3-V-pnenyi-ammo m-~~=VJ~riz carboxylic acid o_z_ z a z_ z_z n- m- z -p eny -ammo car oxy is aci o-z- z s z- z-z et m- z y p ienoxy-acetic acid ester o-r z s z- z-z a m- z y -p enoxyacehc acid ester o-S~-PHz 3 z- z-z a m- z y -p epoxy-acetic acid ester o-~u2 ttz LH3 calz-Ltiz-Ltiz Metnyi m- z N Lti3-pnenoxy-acetic acid ester o-~Uz-Nriz ~H3 c:Hz-~riz-~tiz enemy m- z ~ri3-u-pnenoxy-acetic acid ester o-~uZ ttz cai3 ~;riz-trtiz-Ltiz a m- z N y n--p epoxy acetic acid ester o-SOz-NHz CH3 CHz-CHz-CHz Methyl m- z Yhenoxyacehc acid ester o-SOz-NHz CH3 CHz-CHz-CHz Methyl m-C(=U)NHz C1-phenoxyacehc acid ester o-z- 2 3 2- z-z a m- z y -p enoxyacehc acid ester O-JVZ-NHZ ~:H3 ~aiz tiz-Ltiz Memyi m-~~=uyvriz L trti3-pnenoxy-acetic acid ester o-5u2 tiz LH3 ~tiz-~ty-Ltiz Memyi m-~~=u~mriz N ~ri3-u-pnenoxy acetic acid ester O-JU2-Nri2 Ltl3 LHZ tiZtiz Merry m-~~=u~rVriz L ~ tsn-u-pnenoxy acetic acid ester o-z- z s r r z enoxyacehc m- z aci o-z- z s z r z -p m-C(=NH)NHz epoxy-acetic aci o-z- z s z- r z -p m- z epoxy-acetic aci o-r z 3 2- r z s-P m-C(=NH)NHz epoxy-acetic aci o-z- z s z- z-z 3 m- z -p epoxy-acetic acid o-z- z 3 z- z-z n- m- z -p -epoxy acetic aci o-2 2 3 2- r z enoxyacehc m- =O)NHZ
aci -o-r z s z- z-z -p n~~
enoxyacehc ~~2 acm o-z- z s z- z-z -p m- z enoxyacehc aci o-z- z s z z-2 3- p m- =O)NHz epoxy-acetic aci o-r z ~s CHz-CHz-CHz 3- m- z -p epoxy acetic acid o-z- z a z- z-z n- m- z -p epoxy acetic aci o-z- z 3 z- z-z enoxye m- z ano o-z- z s z- z-z -p m- NHz epoxy-a ano o-z- z 3 2- r z -p m- =NH)NHz epoxy-a ano o-z- z 3 z- z-z 3- p m- z epoxy-a ano o-z- z 3 z z-z 3- - p epoxy-a m- =NIT)NHz ano o-r z 3 z- z-z n- epoxy a m- z -p ano o-z- z ~ i z-z enoxye m- z ano o-z- z 3 z- z-z -p m- z enoxye ano o-r z 3 r z-z -p m-epoxy-a ano o-z- 2 3 2- z-z 3- p rim=C~=O~HZ
epoxy-a ano z- 2 3 2- z-z 3- - p epoxy- m- z a ano o-z- z 3 z- z-z n- epoxy- a m-C~=~)NHz -p ano o-z- z 3 r z-z a m- z y p epoxy-a y ether o-5Vz-Nriz cai, ~tiz-~tiz-~tiz Metnyi m- z ca-pnenoxyeuiyi ether o-5uz Hz c:H3 c:riz-~riz-~tiz Memyi m- z N r-pnenoxy-ecnyi ether o-~u2 Hz LH, ~riz-~riz-~tiz enemy m- z N ~ri3-pnenoxy-ethyl ether o-~u~ ttz ~;ti3 aiz-Ltiz-~aiz memym;ri3-u-pnenoxy- m- z N y ethyl ether o-SOz-NHz CH3 z- r z a m- z y n--p ienoxy ethyl ether o-JVy-1Vr12 lalg ~-tlz-l:riZ-C:tlz Methyl m-l:(=V)Ntlz YnenOXyeTtlyl ether o-z- z s ~-riz-~-riz-~-nz Memyt m-~:(=V)i~riz l:~-pnenoxyemy ether z- 2 3 2- z-z a m- z Y
-p enoxye y ether o-z- z s z r z a m- z Y
s-phenoxyethyl ether o-~Vz-Ntiz ~:ri3 ~:riz-~riz-~;riz Memyi m- z ~ri3-V-phenoxyethyl ether o-JVZ-lVrlz 3 z z-z a m- z Y
n-phenoxyethyl ether o-z- z s z- s P m- z - enY
o-z- z s z- 3 -p m-C~ ~)~z - eny --o-z- z s z- ~ s -phenyl m_C(-~~z -o-z- z s z- ~ 3- p _ eny 2- 2 3 2- 3 j- - p eny m-C
-o-z- z s z- 3 n- eny m-- -p o-z- z s z- s P m~~ O)NHz - enY
o-z- z s z- 3 -p In-C(=O)NHZ
- eny o-z- z s z- 3 -p m-- eny o-z z s z- s 3- p m-C(=O)~z _ enyl o-r z a z- s 3- O-P~eny~ m-C(=O)NHz - - _ z- 2 3 2 3 n_ eny m- -O)~z - _p o-z- 2 3 2- 3 m p-C(=NI~NF
- me o-z- z 3 r 3 -am p-~;(=Nti~~tiz - me -o-z- 2 3 2- , -am P-CON~RHz - me 2- 2 3 2- 3 3 p-l.(=lVr1)1Vt12 - ~ .
me 2 2 3 2- 3 3- p-C(=~)~2 - -anl -me -2- 2 3 2- 3 n- p_C(~H~NH2 - -am me --.
_ 2 2 3 2 3 1 p-~O)~Z
- - me 2 2 3 2- 3 -~ P- 2 - me 2- 2 3 2- g -alll p-l.(=V)1Vr12 - me 2- 2 3 2- 3 3-am p-l.(=V)1Vt12 ' me 2 2 3 2- 3 j- P- 2 - -anl me 2- 2 3 2- 3 n- p-C( - -am me o-r z s z- 3 eny - -ammo-car W .' 1.111.11 oxy m- z is V
acid o-z- 2 3 2- 3 - m-C(=NH)NHz - hen~~no v1 carboxylic acid o-z- z a z- 3 -p m-~~=mry~riz - eny -ammo carboxylic acid o-z- 2 3 2 3 m-C(=NH)NHz s-P~-a~o carboxylic acid o-z- z s r 3 m-C(=NH)NHz - v11 s-~~nyI
ammo carboxylic acid --o-z- z a z- j amino m-C(=NH)NHz - L
V
n--phenyl carboxylic acid o-z- 2 3 2 3 eny m-C(=O)NHz - -ammo carboxylic acid O-JUz-Nriz ~rt3 ~tiz-Sri(-~ri3~-m-pnenyi-ammo m-~(=Vlwriz carboxylic acid O-JUz-Nriz ~ti3 ~riz-Sri(-~rij~-r-pneny-ammo m-~(=Vlwriz carboxylic acid o-z- z s z- 3 a-P m- z - enY
-ammo carboxylic acid o-z- z s z- 3 m- =O)NHz - v11 v' V
-p eny -ammo carboxylic acid o-z- z s z- 3 n- m- z - -p eny -ammo car oxy is aci --o-z- z s z- j et m=~ NH)NHz - y p ienoxy-acetic acid ester o-SVZ Hz s z- s Methyl m- z N - C1-phenoxyacehc acid ester o-SOz-NHz 3 z- s Methyl m- z - F-phenoxy-acetic acid ester O-JVz-NHZ ~ri3 c:riz-~ri~-~ri3~-Memyi m- z ~H3-pnenoxy-acetic acid ester O-JVZ tiz ~ri3 c:riz-pry-~ri3~-Merry m-~~=rrry~riz N ~H3-u-pnenoxy-acetic acid ester o-~u2 Hz LH3 ~riz-pry-~ti3~-Merry m-~~=rrri~Nriz N nn-u-pnenoxy acetic acid ester o-SUz-NHz CH3 CHz-CH(-CH3)-Methyl m- z Yhenoxyacehc acid ester o-OZ=NHz CH3 CHZ -CH3)-Methyl m-C(=U)NHz CH( C1-phenoxyacehc acid ester o-SOz-NHz CH3 CHZ -CH3)-Methyl m- z CH( F-phenoxyacehc acid ester o-SUz-NHz LH3 z- 3 a m- z - y 3-p epoxy-acetic acid ester o-z- z s z- s m-C(=O)NHz - m m a w v a Y
-phenoxy acetic acid ester o-z- z a z- s m-C( ~ jNHz - a.a w a ar v as a Y
n--P
epoxy acetic acid ester o-z- z s z- 3 enoxyacettc m-C(=Nl3jNHz - aci o-i z s r s -p m- NHz - epoxy-acetic aci o-z- 2 3 z- 3 -p m=C(--NH)NHZ
- epoxy-acetic aci o-z- z s r s s- P m-C( NH)NHz - epoxy-aceric acid o-z- z s z- s 3 m- H)NHz - -p epoxy-acetic acid o-z- 2 3 2- 3 n- m-C(=NH)NHz - -p epoxy acetic aci o-z- z s r 3 enoxyacetic m-C(=O)NHz - aci -z- 2 3 2- 3 -p m- z - enoxyacetlc aci z- 2 3 2- s -p m-C(=O)NHZ
- enoxyacehc aci o-z z s z- s 3- p m-C(=U)NHz - epoxy-acetic aci z- 2 3 2- a s- rim-C(=O)NHz - -p epoxy acetic acid o-z- z s r s n- m-C(=V)NHz ' -p epoxy acetic aci o-r z s z- 3 enoxye m-- ano z- 2 3 2- s -p m-C(~NHz - epoxy-a ano o-2 2 3 2 3 -p m- z - epoxy-a ano o-z- z s z- s j- p m- z - epoxy-et ano o-z- z s z- a 5- - p epoxy-a m-C(=NH)NHz - ano o-z- z 3 2 3 n- epoxy a m-~;~=rrrilrrriz - -p ano o-z- z s z- 3 enoxye m- z - ano -z- 2 3 2 3 -p iri=C(=O)NHz - enoxye ano o-z- z 3 z- 3 -p m-- epoxy-a ano o-z- z 3 z- 3 3- p m- )NHZ
- epoxy-a ano o-z- z s z- 3 3- - P epoxy- m-C~ a)NHz - a ano o-2 2 3 2 3 n- epoxy- a m-~:1=a - -p ano ~r~riz o-z z s z- 3 a m- NHz - Y ,J~ ...., p epoxy-a y ether o-2 2 3 2- s a m- )NHz - Y ,_.~ ..
-p enoxye y ether o-z z 3 z- s a m- )NHz - Y ..~ ..
-p epoxy-a y ether o-z- z a z- 3 a m-C(=NH)NHz - Y
P
epoxy-ethyl ether z- 2 3 2 J a m=C(=NH)NHz - Y
;--p epoxy-ethyl ether o-z- z s z- 3 a m- z - y n--p enoxy ethyl ether o-z- z s z- s a m- z - y enoxye y ether o-z- 2 3 2 3 a m- z - Y
-p enoxye y ether o-z z 3 z- s a m- z - y -p enoxye y ether o-z z z- 3 a m-C(=O)~z w.aa ~am.aa~_ Y
-w.aa3_ ~ -ava ua a wa phenoxyethyl ether o-~uz-Ntiz ~ai3 ~nz-~n(-~ti3J-Mecnyi m-~~=ulwnz Win,-u-phenoxyethyl ether o-~uz tiz Win, ~nz-~n~-~n3I-iviemyi m-~~=u~wnz N nn-u-phenoxyethyl ether o-z- z s z- z P m- z - enY
-o-z- z s z- z -p m_ =~)~z - eny o-z- z s z- z -p m-~;(=wn)wnz - eny -o-i z s z- z 3 m- )~
- p eny --o-z- z s z- z s-O- PhenyI m-C(=NH)NHz -o-z- z s z- z n- eny m- z - -p -o-r z s Z_ z p - eny o-z- z s z- z -p ~_~(-O)~z - eny -o-z- z s z- z -p m-C(=O)N)T~
- eny o-z- z s r z s- P m-C~O~FIz - enY
o-r z s z- z a- -P eny m- z - -o-z- z s z- z n- enyI m-C(-O)~z - -p o-z- z s r z m p-C( NH)NHz - me o-z- z s r z -am p-~~=mnyvnz - me o-i z s z- z -am p- )NHz - me o-z- 2 3 2- z j-am p- NHZ
- me o-r z s z- z 3- p-i.~=mnyvnz - -am me o-2 2 3 2- z n- p-~~=wn~wnz - -am me o-r z a z- z m p- ~
- me o-z- z s i z -am p- z - me o-z- z s z z -am P- z - me .
o-z- z s z- z 3-am p- z - me o-z- z s z- z s- p-C(=O)NHz - -am me o-z- 2 3 2 2 n- p_C(-O)~z - -am me o-z- z s z- z eny m- )NHz - -ammo-car ~~ ., oxy is acid o-z- z a z- z eny m-C(=NH)NHz - -ammo carboxylic acid o-z- z s z' z -p m- z - eny -ammo carboxylic acid o-r z 3 z- z j-P m-~~=mnyvn2 - eny -ammo carboxylic acid o-r z 3 z- z j-- -P ~ i,aa~a,aa eny m- z ammo carboxylic acid o-z- z 3 z- z n- m-~:~=mnyvnz - -p eny ammo carboxylic acid o-z- z s z- z eny m-C(=O)NHz - -ammo car oxy is acid o-z- z 3 z- z -p m- =O)NHz - eny -ammo carboxylic acid o-z- z s z- z -p m- _ )NHz - eny -ammo carboxylic acid o-z- z s z- z s-P m- (=O)NHz - enY
-ammo carboxylic acid o-z- z a z- z a~o m- =O)NHz i carboxylic a d o-2 2 3 2- z n- m- 2 - -p eny -ammo car -oxy is aci z- z a rri=C =
- iy z p epoxy-acetic acid ester o-z- z 3 z- z a m- z - y -p enoxyacehc acid ester o-z- z 3 z- z a m- z - y -p epoxy-acetic acid ester o-z- 2 3 2 2 a m- z - Y
3-p epoxy-acetic acid ester o-~uz-wriz Sri, z- z a m- z - y -p epoxy-acetic acid ester o-- -- z ( -~z)--~~yl m-C(=NH)NHz Bn-O-phenoxy acetic acid ester o-SOz-NHz CH3 CHz-CH(-NHz)-Methyl m-C(=U)NHz Yhenoxyacehc acid ester o-SOz-NHz CH3 CHz-CH(-NHz)-Methyl m-C(=U)NHz C1-phenoxyacehc acid ester o-SOz-NHz CH3 CHz-CH(-NHz)-Methyl m- z r-phenoxyacehc acid ester o-~uz-wtiz Lti3 ~tiz-qty-Ntiz~-Memyi m-~~=u~wriz ~ri3-pnenoxy-acetic acid ester O-JUz tiz Lti3 ~;tiz uvtizl-Memyi m- z w ~;ry ~ri3-u-pnenoxy acetic acid ester O-JVz tiz Lti3 ~riz-qty-wtiz~-enemy m-~~=uyvriz w tsn-u-pnenoxy acetic acid ester o-r z 3 z- 2 enoxyacehc m- z - aci o-z- z 3 z- z -p m-C(=NH)NHz ~ - epoxy-acetic acid o-z- z 3 z- z -p m-- epoxy-acetic aci o-z- z s r z 3 p m-C(=NH)NHz - epoxy-acetic aci o-z- z 3 z- z m-C(=NH)NHz - ~.~.
~.
s--Phenoxy=acetic acid o-z- z 3 z- z n- m-C(=NH)NHz - -phenoxy acetic acid o-2 2 3 2- z enoxyacehc m- z - aci o-z- z s z- z -P m- )NHz - enoxyacehc -aci o-z- z s z- z -p m- z - enoxyacehc aci o-z- z s z- z 3- p m-C
- epoxy-acetic aci o-z- z 3 r z s- m-- -P
epoxy acetic acid o-r z s z- z n- m- z - -p epoxy acetic aci o-z- z s z- z enoxye m- )NHz - ano -o-z- z s z- z -p m- 2 - epoxy-a ano o-z- z a z- z -p m-t,~=mryvriz - epoxy-a ano o-r z s z- z 3- p m-- epoxy-a ano o-r z 3 z- z 3 - p epoxy-a m-C( NH)NHz - ano o-z- z s z- z n- epoxy a m-~~=mryvriz - -p ano o-z- z 3 z- z enoxye m=C(=O)NHz - anol --o-z- z a z- z -p m-~~=uyvri2 - enoxye ano o-z- z 3 z- z -p m-- epoxy-a ano o-z- z s z- -~i)-3- p m-C(=O)NHz ( epoxy-ethanol-o-z- 2 3 2- z s- - P epoxy- m- z - a ano o-z- z 3 z- z n- epoxy- a m-- -p ano o-z- z 3 z- z - ma .~ mu m m- )NHz i m m m a y p epoxy-a y ether o-z- z s z- z a m- =NH)NHz - Y
-P
enoxye y ether o-~uz-wriz 3 ~riz-pry-wri2~-a m- z y -p epoxy-a y ether O-JUz-writ ~ri3 ~riz -rrriz)-enemy m-~~=mryvriz Sri( ~ri3-pnenoxy-ethyl ether o-z- z s z- z a m- z - Y
-P
epoxy-ethyl ether - -o_Z~ z 3 2 z - a y m_ n _ _p enoxy ethyl ether o-~u2 riz l:ri3 l;riz y-wriz)-Memy rnenoxyemy m-~~=u)wtiz w 1:r ether O-JUz-1Vr12 1.r13 Lri2-LW-~ri2)-Memyi la-pnenoxyetnyim-Lt=u)ivtiz ether o-~uz-wriz l:ri3 ~riz-ury-r~riz)-nnetny r-pnenoxyemym-ut=u)wriz ether O-JUz-wriz l:ry l:riz-l:ry-Nnz)-Memym:rij- m-~;t=u)Ntiz phenoxyethyl ether o-~u2 tiz ~ri3 l:riz-Sri(-Nriz)-nnemyi 1:n3-u- m- z N
phenoxyethyl ether o-JUZ-Nt12 1x13 l;tlz-lal(-iVtl2)-Memyl tin-u- m-l;~=u)Nriz phenoxyethyl ether o-z- z s z- - n P eny m- z -o-z- z s z- - n -p eny m_C~_~)~z _ _ o-z- z s z- - n -p eny m-_ z- 2 3 2- - n 3-p eny m- z -o-r z s z- - n 3_ _p eny m-CO~z -o-z- z 3 z- - n n_ _p eny m- z -o-z- z s z- - n p eny m-~~=u)wriz -o-z- z s z- - n -p eny m- z _ z- z s z- - n -p eny m-_ o-z- z s z- - n j-p eny m_ )~
-o-r z s z- - n 3- -p eny rn-C~~
-o-z- z s z- - n n_ _p eny m--o-r z 3 z- - n m me p-1:~=r~ri)wriz -o-z- 2 3 2- - n -am me p- z -z- 2 3 2- - n -am me p=C~)~z _ o-r z 3 z- - n 3-am me P-C~
-o-z- z s z- - n j_ _am me p-~~=~ri)~riz -o-z- z s z- - n n- -am me p- z -o-z- z s z- - n i me .. P- z -z- 2 3 2- - n -am me p-_ o-z- 2 3 2- - n -am me p- z -o-z- z s z- - n j-am me p_ z - -o-z- z s z- - n 3_ =~~e p_C~=O)~z -o-r z s z- - n n- -am me p-C( O~PHz -o-z- z s z- - n eny -armno=carboxylicm- )NHz -acid O-JVZ-Nriz lai3 z- - n eny -ammo m- z -carboxylic acid o-~uz-Ntiz lai3 l:riz-l:ry-~sn)-r-pnenyi-ammo m- z carboxylic acid o-JUz-NriZ 1x13 (alz-C:ri(-tin)-1:ri3-prienyl-ammom-carboxylic acid O-~Uz-NriZ lai3 Ltiz-lay-tsn)-3_ _p eny ammo m- z carboxylic acid o-~u2 riz lai, laiz-lay-rsn)-n- -p eny ammo m- z N
carboxylic acid o-~u2 tiz l:rt3 laiz-l:ry-rsn)-rnenyi-ammo carooxyncm-1;~=u)ivriz w acid O-JUz-wtiz lai, l:riz-l:ry-tsn)-l.;i-pnenyi-ammom-~~=u)wriz carboxylic acid O-JUz-Nriz Sri, laiz-l:ry-tsn)-r-pnenyi-ammo m-1:~=u)~riz carboxylic acid O-JUz-wtiz l:ri3 uriz y-~sn)-l:ri3-pnenyi-ammom-~~=u)~riz ur carboxylic acid o-JUz r12 1:ri3 lal2-lJri(-tSn)-1:ri3-u-pneriyl-ammom-1:~=u)lVrlZ
carboxylic acid o-2 2 3 z- - n n- _p eny -ammo m- z ~
-car oxy is aci o-z- z s z- - a m-n y - p epoxy-acehc acid ester o-SOz-NHz 3 z- - a m- z n y - -p enoxyacehc acid ester o-SOz-NHz CH3 CHz-CH(-Bn)-Methyl m- z F-phenoxy-acetic acid ester O-~uz-Ntlz ~rij utiz-uti(-~sn)-Mewyi m-~l=wri)wriz uri3 pnenoxy-acetic acid ester o-~Vz-Nriz Lti, Ltiz-Lti(-tsn)-Merry m-u(=wti)Ntiz uti3-u-pnenoxy-acetic acid ester O-JVz-lVriy :rij utizway-tsnl-Merry m-tJ~=~ri)~riz rsn-u-pnenoxy acetic acid ester o-SOz-NHz CH3 CHz-CH(-13n)-Methyl m-C(=U)NHz Yhenoxyacehc acid ester o-SOz-NHz CH3 CHz-CH(-I3n)-Methyl m-(:(=U)NHz C1-phenoxyacehc acid ester o-SOZ Hz CH3 CHz-CH(-t3n)-Methyl m- z N F-phenoxyacehc acid ester o-z- z 3 r n m_C(=p)~2 - ....
a Y
P
epoxy-acetic acid ester o-z- z 3 z- - a m-C(_O)~2 n Y
- s-:
P
epoxy acetic acid ester o-~uz Hz ~:ri3 z- n a m- z N - y n--p epoxy acetic acid ester o-z- z s z- n enoxyacehc m- z - aci -o-z z 3 z- n -p m- z - epoxy-acehc aci o-z- z 3 z- n -p m-(:(=NH)NHz - epoxy-acehc aci o-z- z s z- - 3 p m-C(=NH)NHz n epoxy-acehc - aci o-r z s r n 3- m- z - -p epoxy-acehc acid o-r z s r n n- m- z - -p epoxy acehc aci o-z- z a z- - enoxyacehc m-C(=O)NH2 n acW
-o-z- z , z- - -p m- z n enoxyacehc - aci o-z- z 3 z- - -p m-n enoxyacehc - aci o-z- z s z- - 3-p iri=C(=O)NHz n epoxy-acetic - acid o-SOz-NHz CH3 CHz-CH(-J3n)-3- m- z -p epoxy acehc acid o-z- z s z- - n- m- z n -p - epoxy acehc aci o-z- z 3 2 - enoxye m- (=NH)NHz n ano -o-2 2 3 2 - -p m- z n epoxy-a - ano o-z- z j z- - -p m-~~=~ri)wriz n epoxy-- a ano o-2 2 5 2- - 3- p m- z n epoxy-a - ano -o-z- 2 3 z- - 3- - p epoxy-ethanol~~NHz n -o-z- z 3 z - n- epoxy a m- z n -p ano --o-2 2 3 2 - enoxye m=C(O)NHz n ano -o-z- z s z- - -p m- z n enoxye - anol o-z- 2 3 z- - -p m- z n epoxy-a - ano o-z- z 3 z- - s- P m-~~=u)~riz n epoxy-a - ano o-z- z s z- - 3 - p epoxy- m- z n a ano -o-z- z s z- - n- epoxy- a m-n -p ano -o-z- z 3 z- - a m- 2 n y - p epoxy-a y ether o-~uz-Ntiz ~ai3 2 - a m- z n y - -p enoxye y ether o-~uz-ivtiz s z- - a m- z n y - -p epoxy-a y ether o-z- z s z- - a m- z n Y
- s-P
epoxy-ethyl ether o-~u2 tiz ~ri3 ~riz-pry-tsn)-enemy m-~~=wri)wriz N ~ri3-u-pnenoxy-ethyl ether o-Z- ~z z- - n a y n_ _p ienoxym- z -ethyl ether o-z- 2 3 2- - n a y enoxye y m- z -ether o-z- z 3 r - n a y -p enoxye m- z - y ether O-JU2-lVri2 3 Y - n a y -p enoxye m- z - y ether o-~uz-Nriz ~rij ~riz-~ri~-rsn~- enemy ~ri3- m-~~=u~r~riz phenoxyethyl ether o-z- z s z- - n a Y 3- m- z -phenoxyethyl ether O-lu2 tiz ~:ri3 ~riz-~ri~-~sn~- nneuryi tsn-u- m-~.~=u~r~riz ~
phenoxyethyl ether O-JUZ-1Vt12 ~:ri, ~aiz-qty-~tiz-pnenyi m-t.~=~tiyvriz COOCH,)-O-JUz-wriz ~ri3 ~riz-Sri(-~riz-m-pnenyi m-~~=~rywriz COOCH,)-O-JUy-1Vt12 l;tlg l:rl2-lal~-1x12-r-pnenyi m-~;~=~ri~r~riz COOCH,)-o-~uz-wriz ~.;ri3 ~riz-~ri~-~riz-~ti3-pnenyi m-~:~=wri~wtiz COOCH3)-o-~u2 tiz ~:ri3 uri2 ri2-3_ _p eny m- z w pry-~
COOCH3)-O-JUy-lVtiz 1:ri3 1:ri2-l;ti~-l;tiz-n_ -p eriy m-COOCH,)-o-2 2 3 2 z- P enY m- z COOCH3)-o-~uz-lvtiz t.ri3 ~;tiz-qty-caiz-m-pnenyi m-~~=u~Ntiz COOCH,)-o-~uz-mttz s z- z- -p eny m- z COOCH3)-o-z- z 3 z- z- 3 P enY ' m- z COOCH,)-O-JUZ-Nri2 1:ri3 lalZ-l;ri(-1;t12-~ti3-u-pnenyi m-~~=u~~riz COOCH3)-O-JVz-Nriz uti3 uriz-pry-uriz-nn-u-pnenyi m- z COOCH3)-o-~uz-~ttz uti, uriz-pry-utiz-Amime p-~~=~ri~~riz COOCH3)-O-JUZ-wriz ~;ri, ~riz-pry-~aiz-~;i-amime p-~~=mryr~riz COOCH3)-O-JUz-wriz uri3 ~riz-pry-~riz r-amime p-~~=r~ry~riz COOCH,)-o-~uZ riz ~;ti3 ~riz riz-~ti3-amime p-~~=r~tyr~tiz ~ ~ti~-~
COOCH3)-o-auz riz ~ri3 ~riz-pry-~riz-~ri3-u-amime p-~~=mryr~riz w COOCH,)-O-JUz riz ~ri3 ~nz-pry-~tiz-rsn-u-amime p-~~=~ryr~tiz N
COOCH3)-O-JUZ-~riz ~;ri3 t~riz-pry-~riz-t~mime p-~:~=u~r~riz COOCH3)-O-JUZ-~riz ~ri3 ~riz-pry-~riz-m-amime p-~~=u~~riz COOCH3)-O-JU2-lVri2 3 2- ~ -am me p- z COOCH3)-o-r z s z- z- 3-am me p- z COOCH3)-o-~uz-Nriz uri, ~riz-pry-~riz-uri3 u-amime p-~~=u~~riz COOCH3)-o-z- z s z- z- n- -am me p- z COOCH,)-o-z- z 3 z- z- eny -ammo-car m- z oxy is COOCH,)- acid o-SU2 Hz c.;H3 CHz-CH(_CHz-CI-Yhenyl-ammo m-C(=NH)NHz N
COOCH3)- carboxylic acid O-JUZ riz ~:ri3 ~;riz-Sri(-~:rizr-pnenyi-ammo m-~~=Nrywriz w COOCHj)- carboxylic acid O-JVz-wriz ~ri3 ~riz-Sri(-~riz-uri3-pnenyi-ammom-~~=NryNriz COOCH,)- carboxylic acid ~-'~U2-~ri2 3 2- z- ~-ris-~-Pnenyi m- z armno COOCH,)- carboxylic acid O-JUz-Ntiz t,ti3 ~riz-pry-t,tiz-tsn-u-pnenyi m-~:~=~ryvriz armno COOCH3)- carboxylic acid o-z- z s z- z- eny -ammo car m- z oxy is COOCH3)- acid O-lV2-Nrlz l;rig 1:r12-lal(-lily-m-pnenyi-ammo m-~~=v~r~riz COOCH3)- carboxylic acid o-~uz-Nriz ~ri3 ~riz-pry-~riz-r-pnenyi-ammo m-~~=~~~riz COOCH,)- carboxylic acid O-JUZ-Nri2 1:ri3 ~riz-t.;ry-~riz-~:ri3-pnenyi-ammom- z COOCH3)- carboxylic acid o-~uz-NHz c:ri3 ~tiz-~:ri(-~tiz-3- -p eny -ammo m- z COOCH3)- carboxylic acid o-lUZ HZ 1;r13 l;tlz i2-tin-U-pneriyl-ammom-l:(=V)lVtlz N l;tl(-l:r COOCH3)- carboxylic acid o-SOz-NHz CH3 CHz-CH(-CHz-Methyl phenoxy-aceticm-C(=NH)NHz COOCH3)- acid ester o-SUz-NHz CH3 CHz-CH(-CHz-Methyl Cl-phenoxyacehcm-C(=NH)NHz COOCH3)- acid ester ri-z- 2 3 2- z a y -p enoxy- m- z acetic COOCH3)- acid ester o-~u2 riz ~ti3 ~riz iz-Memyi ~ri3-pnenoxy-m- z N ~rt~-~r COOCH,)- acetic acid ester o-~uz-Ntiz ~ri3 ~riz-qty-~riz-Memyi Sri,-u-pnenoxy-m- z COOCH,)- acetic acid ester o-~uz tiz ~:ri3 ~rtz-Sri(-~riz-Memyi rsn-u-pnenoxym- z N
COOCH3)- acetic acid ester o-SOz Hz CH3 CHz-CH(-CHz-Methyl Yhenoxyaceticm- z N
COOCH3)- acid ester o-SUZ Hz CH3 CHz-CH(-CHz-Methyl Cl-phenoxyacehcm- z N
COOCH,)- acid ester o-SOZ Hz CHI 2 z- a y -p enoxyacericm- z N
COOCH3)- acid ester o-~uz-Ntiz ~ai3 ~tiz-~tt~-~;ti2 nnemym:ri3-pnenoxy-m-l;(=V)1Vr12 COOCH3)- acetic acid ester o-~u2 tiz uri3 uriz i2 enemy Sri,-u-pnenoxym-~~=v~wriz N pry-~r COOCH3)- acetic acid ester o-~u2 tiz ~.;ti3 Lty~ty-t_;tiz Memyi ~sn-u-pnenoxym-~~=u~r~riz N
COOCH3)- acetic acid ester o-SOz-NHz CH3 CHz-CH(-CHz-Yhenoxyacehc m-C(=NH)NHz acid COOCH3)-o-SUZ Hz CH3 CHz-CH(-CHz-Cl-phenoxy-aceticm-C(=NH)NHz N acid COOCH3)-o-SUz Hz CH3 CHz-CH(-CHz-r-phenoxy- aceticm-C(=NH)NHz N acid COOCH,)-o-SUz-NHz CH3 CHz-CH(-CHz CH3 phenoxy-aceticm-C(=NH)NHz acid COOCH,)-o-SUz-NHz CH3 CHz-CH(-CHZ CHj-U-phenoxy-aceticm-(:(=NH)NHz COOCHj)- acid o-SUz-NHz CH3 CHz-CH(-CHz-tan-U-phenoxy m-C(=NH)NHz acetic acid COOCH3)-o-SUz Hz CHj CHz-CH(-CHZ Yhenoxyacetic m- =U z N acid COOCH,)-o-z- z a z- z- -p enoxyacehc aci ~.~ ,.,~.,.
m-COOCH,)-o-z- z CH3 MHz-CH z- -p enoXyacehc m-C(=O)NHz - acid COOCH3)-o-SOz-NHz CH3 (:Hz-C;H(-CHz-CH3-phenoxy-acehcm-C:(=U)NHz acid COOCH3)-o-SOz Hz C;H3 C;Hz-C;H(-(:Hz-C:H3 U-phenoxy m-C;(=U)NHz N acehc COOCH3)- acid o-~z-Hz CH3 CHz-CH(-CHz Bn-U-phenoxy m-C;(=U)NHz acehc acid COOCH3)-O-JUz-Nriz cai3 unz-uril-uriz-rnenoxyemanoi m-~l=~n)~riz COOCH3)-o-~uz-ivttz Lria z- z- -p epoxy-a ano m- z COOCH3)-O-JUz-Nriz c:rt3 laiz-lail-l:riz--p epoxy- a ano m- z COOCH3)-o-JUz-NHz cal3 r z- 3-p epoxy-a ano m- z COOCH3)-O-JUz-Nriz cal3 z- z- s- . -P epoxy-a m- z ano COOCH3)-o-5U2-NHz 1.113 z- z n- -p epoxy a m- z ano COOCH,)-o-5U2-NHz l;tl3 l;tlz-fall-l;tlz-rnenoxyemanoi m-l:l=u)ivriz COOCH,)-o-5Uz-NHz t;tl3 caiz-latl-catz--p enoxye ano m- z COOCHj)-O-JUz-NHz 3 z- z- -p epoxy-a ano m- z COOCH,)-o-~u2 tiz lai3 laiz-fail-laiz-lai3-pnenoxy-emanoim-1.1=u)ivriz N
COOCH3)-o-SVz-Nriz c:ti3 c:riz-l:ril-lai2 cai3-u-pnenoxy- m-l:l=u)wriz emanoi COOCH,)-o-~Uz-Nriz Lri3 uriz-uril-unz-~sn-u-pnenoxy- m- z emanoi COOCH3)-O-JVz-Ntlz lat3 l:riz-l:ril-l:riz-Merry pnenoxy-emym-l.l=mri)wriz COOCHj)- ether o-~uz-Ntiz lai3 laiz-l:ril-l:riz-enemy la-pnenoxyemyim-l:l=wri)wriz COOCH,)- ether O-JVz-Nriz lai3 laiz-lail-laiz-Merry r-pnenoxy-emyim- z COOCH,)- ether O-JVz-Nriz c:rt3 laiz-fail-l:tiz-a Y 3-P epoxy- m- z COOCH,)- ethyl ether O-JVz-Ntlz lai3 laiz-fail-laiz-Merry ~ri3-u-pnenoxy-m- z COOCH~)- ethyl ether O-JVz-Nriz lai3 l:riz-l:ril-l:rizMeuiyi rsn-u-pnenoxym- z COOCH,)- ethyl ether O-JUz-lVriz lai3 laiz-t_;til-laiz-a y enoxye y m- z COOCHj)- ether o-JVz-Nriz lai3 r r a y -p enoxye m- z y COOCH3)- ether O-JUz-Ntiz l:ri3 unz-uril-uriz-Metnyi r-pnenoxyetnyim-~l=u)wriz COOCHj)- ether o-alJ2lVtiz 1x13 laiz-fall-l:riz-Melllyll.;ri3- m- z COOCH3)- phenoxyethyl ether O-JUz-lVtlz 1;t13 z- z- a y 3- m- z COOCH3)- phenoxyethyl ether O-JVz tlz 1x13 l.rlz-l.;tll-l;riz-MeLllyl tSn-u- m-l:l=V)lvrlz lV
COOCH3)- phenoxyethyl ether o-JVz-iVtiz l;rlg l;tlz-lull-laiz-pnenyl m-l:l=1Vri)lvriz CHz-OH)-O-JUz-iVtl2 1:ri3 1:ri2-l:rll-l=rlz-la-pneny m-l:l=wri)mriz CHz-OH)-o-z- z 3 r x- -p eny m-CHz-OH)-o-~Ux-NHx 1:H3 l;Hx-l;Hl-l:Hx-C:H3-pneriyl m- x CHx-OH)-O-JUx-NHx LH3 ~riz-aril-c:Hx-LH3-U-pnenyl m- z CHx-OH)-o-JUz-NHz s z' z- n- -p eny m- z CHx-OH)-o-~uz Hz ~H3 ~riz-~ril-~riz-pnenyl m- z N
CHx-OH)-o-JUz Hx 1:H3 l:Hx-l:Hl-l:Hx--p eny m- x N
CHx-OH)-o-aux-NHx c:H3 ~riz rix_-p eny m- z aril-~
CHx-OH)-O-JUx-NHx (:H3 t,riz tix-~ti3 pnenyi m-t,l=~~Nrix pail-t, CHx-OH)-O-~Ux-NHx ~:ri3 ~aizw;tyu;Hz-~ti3-u-Pnenyt m- z CHz-OH)-o-5Uz Hx ~H, ~Hx-~Hl-LHZ rsn-u-pnenyi m- z N
CHz OH)-o-~ux-NHz 1:r1, x- z 11i1e p- x CHI OH)-o-z- z s x- z -am me p-C( NH)NHx CHz OH)-o-JVx-NHx 1:H3 x- z- -am me . p- x CHx-OH)-o-5U2 Hx s x- z' 3-am me . p- x N
CHZ OH)-o-5Uz-NHz ~:H3 ~:Hz iz-~:ri3-v-anmne p-~:(=r~nyvrix c:Hl-~a CHz-OH)-o-~Vx-NHx 1:H3 z- x- n- -arid me p- x CHz-OH)-o-5Ux-NHx 3 r z- me p- x CHx-OH)-O-5Vx-NHx C;H3 l;Hx-l:Hl-l;Hx-l:1-anllme p-t_;l=V)i~riz CHx-OH)-o-5Ux-NHx 1:H3 (:Hx-l;Hl-l:Hx_r-am11I1e p- x .
CH2 OH)-O-JUx-NHx l:Hg Calx-l;ril-lair-l;rig-anllllle p- x CHx-OH)-O-JVx-NHx 1:H3 l;Hx-l:ril-l:Hx-l.;tl3-u-anllme p- x CHz OH)-o-~Uz-NHx 1:H3 lalx-fat(-laix-tsn-V-amime p-~,(=vJmriz CHx-OH)-O-5Ux-NHx 1.H3 l,Hz Hx-Ynenyl-allllll0-CarDOXyIICm-l:l=lVt1)lVtlx C.HI-l;
CHx-OH)- acid O-JUx-NHx C:H3 (.;Hz rix-eriy -aIrilno m- x l;Hl-l.:
CHz-OH)- carboxylic acid O-5Ux-NHx C:H3 l:Hz Hx--p eriy -amino m- x l:Hl-l;
CHx-OH)- carboxylic acid O-~Ux-Nrix 1;H3 l:Hz Hx-LH3-pnenyi-ammo m-~(=~ry~riz l:Hl-t;
CHx-OH)- carboxylic acid o-JUx-NHx C:H3 lalz rix-3 -p eriy ammo m- x l:ril-l;
CHx-OH)- carboxylic acid O-5Uz Hx C.;H3 l:Hx-l:Hl-l;Hx-tin-U-prieriyl m- x N aIrilIio CHx-OH)- carboxylic acid o-~u2 Hz LH3 ~riz-~ry-~tiz-rnenyi-ammo cardoxyncm-~(=v~r~rix N
CHx-OH)- acid o-JUz Hx 1;H3 l:rix-l:ril-l:Hx-l:l-prienyl-amlriom- x N
CHx-OH)- carboxylic acid O-~Ux-NHx LH3 t,tizwayuaiz r-pnenyi-ammo m- z CHz-OH)- carboxylic acid o-z- z a z- z- 3-P eny -ammo m-~~=~JNriz CHz-OH)- carboxylic acid o-auz-~tiz ~;ri, ~;riz-~:ry-t_;tiz-~;tij-v-pnenyi-ammom-~a=~~~riz CHz-OH)- carboxylic acid O-JUz-Ntiz ~:ri3 ~:riz-~;ry-t_;tiz-tsn-u-pnenyi-ammom- z CHz-OH)- carboxylic acid o-SOZ Hz 3 r z- a Y p enoxy-aceticm- z N
CHz-OH)- acid ester o-SOz-NHz CHI z- z- a y -p enoxyacehcm- z CHz acid ester OH)-o-SOz Hz CHI z- z- a y -p enoxy- m- z N acetic CHz-OH)- acid ester O-JVZ-Nri2 ~;ty :riz-pry-~;riz memym:ri,-pnenoxy-m-~t=mry~riz CHz acetic acid ester OH)-o-~uz-Ntiz uri3 uriz riz-enemy ~ri3-u-pnenoxy-m- z pry-~
CH2 acetic acid ester OH)-o-~uz-Ntiz ~ti3 ~riz-~ryu:ri2 nnemyi rsn-v-pnenoxym- z CHZ acetic acid ester OH)-o-SO~ Hz CH3 CHz-CH(-CHz- Methyl Yhenoxyacehcm- z N
CHz-OH)- acid ester o-SOZ Hz CH3 CHz-CH(-CHz Methyl Cl-phenoxyacehcm-(:(=U)NHz N
CHz acid ester OH)-o-SOz-NHz CH3 CHz-CH(-CHz- Methyl r'-phenoxyacehcm-(:(=U)NHz CHz-OH)- acid ester O-~uz-Ntiz uri, uriz riz-enemy ~ri3-pnenoxy-m-~t=v~r~riz ury-~:
CHz-OH)- acetic acid ester o-~uz-ivnz t~ty trtiz-tit-~aiz Memyi ~ri3-u-pnenoxym-~.t=v~r~riz CHz acetic acid ester OH)-O-JVZ-NHz ury unz-~ril-uriz-nnemyi rsn-u-pnenoxym-~t=~yvriz CHz-OH)- acetic acid ester o-SOZ Hz CH3 CHZ-CH(-CHz- Yhenoxyacehc m- z N acid CHz OH)-o-SOZ Hz CHj CHz-CH(-CHz- -p enoxy-acetic m- z N aci CHz OH)-o-z- z CH3 CHz-CH(-CHz- F-phenoxy- aceticm-C(=NH)NHz - acid CHZ
OH)-o-Oz-~ CH3 CHZ Hz- CH3-phenoxy-aceticm-C(=NH)NHz CH(-C acid CHZ
OH)-o-Uz-MHz CH3 CHZ Hz- 3- -p enoxy-aceticm- z CH(-C
CHz acid OH)-o-Oz-NHz CHj CHz-CH(-CHz- n- -p enoxy aceticm- z aci CHz-OH)-o-SOz-NHz CHj CHz-CH(-CHz- Yhenoxyacehc m- z acid CHz-OH)-o-Oz-NHz CH5 CHz-CH(-CHz- Cl-phenoxyacehc m- z acid CHz OH)-o-SOz-NHz CH3 CHz-CH(-CHz- F-phenoxyacehc m- z acid CHz-OH)-o-SOZ Hz CH3 CHz-CH(-CHz- 3-p enoxy-aceticm- z N aci CHz-OH)-o-SUz-NHz CH3 CHz-CH(-CHz- (:H3-U-phenoxy m-(:(=U)NHz acetic CHz-OH)- acid o-SOz Hz CH3 CHz-CH(-CHz- J3n-U-phenoxy m-(:(=U)NHz N acetic acid CHz OH)-o-~uz-Nriz ~ti3 ~tiz riz-rnenoxyemanoi m- z pry-~
CHz OH)-o-~uz-Ntiz t_;ti3 ~aiz tizwa-pnenoxy-emanoim-~:~=~ry~riz ~;ty-~
CHZ
OH)-o-~uz-Ntiz ~ai3 Ltiz-gay-~aiZ -p enoxy- a ano m- z CHz-OH)-o-~uz-Ntiz 3 z- z- 3-p enoxy-a ano m- z CHz OH)-o- z z 3 z- z- 3- -p enoxy-a m- z ano CHz-OH)-o-~uz-Nriz c:ri3 uriz-aril-utiz-Iin-u-pnenoxy m-~:l=Nri)Nriz emanoi CHz-OH)-o-~uz-Nriz ~ri3 ~-riz-~nl-~riz-rnenoxyemanoi m-~(=u)wriz CHz-OH)-O-~Vz-Nriz Sri, ~nz-~ril-~nz-~l-pnenoxyemanoim-~l=u)Nriz CHz-OH)-O-JUZ-NHZ Lti3 ~ti2-~til-Lriz-r-pnenoxy-emanoim- z CHz-OH)-o-'uz-Ntiz c;ti, z- Z ~ai3-pnenoxy-emanoim- z CHz-OH)-o-~UZ-Ntlz Lti3 ~:rizwayu:rizw;ti3w-pnenoxy- m-~;(=u)ivriz emanoi CHz-OH)-o- z- z a z- z- n- -p epoxy- m- z a ano CHz-OH)-O-JUz-Nriz ~ai3 ~;tiz-pry-~:riz-enemy pnenoxy-ecnyim-~:(=ivri)ivriz CHz-OH)- ether o-JVZ-Nriz c,ti3 ~ai2-Lti(-~:riz-a y -p enoxye m- z y CHz-OH)- ether o-JVz Nttz ~ti3 ~riz Sri(-~riz-a y -p epoxy-a m- z y CHz-OH)- ether o-JVZ Ntiz ~ri3 ~riz-~til-~riz-a Y 3-P epoxy- m- z CHz-OH)- ethyl ether o-JVZ Ntiz uri3 uriz-uri(-uriz-enemy ~ri3-u-pnenoxy-m-~l=wri)ivriz CHZ OH)- ethyl ether O-JVz-Nriz ~:ri3 ~:nz-~ril-Lriz-Metnyi un-u-pnenoxym-~.l=ivri)ivriz CHz-OH)- ethyl ether O-JUy-Ntl2 Lti3 uti2-~ril-uty-nnemyi rnenoxyemyim-~;(=u)wriz CHz-OH)- ether o-~uz-Nriz ~ri3 ~ri2 ~ril-~riz-Memyi m-pnenoxyemyim-~(=u)ivriz CHz-OH)- ether o-auz-Nriz ~ai3 ~aiz ~ti(-~ai2-Memyi r-pnenoxyemyim- z CHz-OH)- ether o-JUz Nti2 1x13 l:riz l.:ril-l:riy-Metnymal3- m- z CHz-OH)- phenoxyethyl ether O-JUz-Ntiz Lti3 ~ti2-aril-~tiz-enemy ~ri3 u- m- z CHz OH)- phenoxyethyl ether o-JUz NHz Cai3 (aiz-~:ri(-~ai2-a y n- m- z CHz-OH)- phenoxyethyl ether o-auz Nttz ~ai3 ~aiZ t_;til-~aiz-pnenyi m-~.(=ivri)ivriz C(=O)-N-morpholino)-O-~UZ-Nri,_ c.ai3 ~ai2-pail-Ltiz-~;i-pnenyi m-~(=ivri)ivriz C(=O)-N-morpholino)-O-JU2-Nri2 c:ri, ~riz aril-~ri2-r-pnenyi m-~(=ivri)ivriz C(=O)-N-morpholino)-av mW .ai m v.y-w v.m a a v~ a.ya.a o- z- 2 3 2- z a-P enY m- z C(=O)-N-morpholino)-O-JVZ-Ntl2 Lti3 Ltiz-aril-Ltiz-~ti3-u-pnenyi m-~l=Nri)ivriz C(=O)-N-morpholino)-.
o- z- z s z- z- n- m- z -P enY
C(=O)-N-morpholino)-O-~uz-Nriz uti3 utiz-aril-~rizpnenyi m-~(=u)wriz C(=O)-N-morpholino)-o- z- 2 3 2- z- -p eny m- )~Z
morpholino)-o-~uz-mtiz l;ri3 l:rlz-l:rll-caiz-r-phenyl m-l:l=u)lvrlz C(=O)-N-morpholino)-o-~uz-Ntiz l:ri3 ~riz l:ril-lalz-l;ti3-phenyl m-l:l=u)lvrlz C(=O)-N-morpholino)-O-JUZ lVriz 1x13 lain-l.;ril-1x12-1:ri3-V-phenyl m-l:l=V)lVriz C(=O)-N-morpholino)-O-JVz-lVriz 1:r13 l:rlz-l:rll-~tiz-tsn-u-phenyl m-l:l=v)lvrlz C(=O)-N-morpholino)-o-~uz-lvriz l:rl3 l;rl2l;rll-l:rlz-Anllme p-~l=IVrI)lvrlz C(=O)-N-morpholino)-O-JUZ-1Vt12 l;tl3 1:ri2-fail-lainl;l-anllme p-l:l=lVt1)lVri2 C(=O)-N-morpholino)-o-JVZ lvrlz cal3 l;tlz-fail-lalz-r-anllme p-l:l=lvrl)lvrlz C(=O)-N-morpholino)-O-JUZ-Ntl2 1x13 1x12-fail-lain-1x13-aI111me p-l;l=lVt1)lVti2 C(=O)-N-morpholino)-O-lV2-Nti2 lal3 1x12-fall-l;tiz-1x13-u-anllme p-l:l=lVt1)lVtlz C(=O)-N-morpholino)-.
o-JU2 Nrl2 laig C.tl2-l;tll-1x12-t5n-u-anllme p-l:l=IVtl)1Vt12 C(=O)-N-morpholino)-O-5u2-1Vr12 1:r13 1;t12-l;tll-1:r12-Amlme p-l:l=u)iVrl2 C(=O)-N-morpholino)-O-JVZ-Nrl2 l;tlg lalz l:tll-1;t12l:l-anllme p-l:l=u)lvri2 C(=O)-N-morpholino)-O-JU2-NrlZ C.;rl3 1x12-fall-lltly-r-anllme p-l;l=V)lVrlz C(=O)-N-morpholino)-O-JU2-1Vr12 laig 1.112-fail-l;rlz1x13-anllme p-l:l=u)lvtlz C(=O)-N-morpholino)-o-aVz-lvtlz c:rl3 l:riz-l;ril-l:rizl:rij-u-anllme p-l:l=v)lvriz C(=O)-N-morpholino)-z- z s z- z- p- =O)NHz is v . w,l n- -and me -C(=O)-N-morpholino)-o-~uz-lvtlz 1x13 lalz-~ril-1-rlz-rnenyl-ammo-carooxyncm-l:l=lvti)lvrlz C(=O)-N- acid morpholino)-o-~uz-lvtiz 1x13 lalz-l;tll-~riz-1:1-rnenyl-ammo m-l:l=lrrl)lvrlz C(=O)-N- carboxylic acid morpholino)-o-~uz lvtlz lai3 lalz-loll-lalz-r-phenyl-amino m-l:l=lvrl)lvrlz C(=O)-N- carboxylic acid morpholino)-O-JUz iVri2 l:rig 1:ri2-l:rll-l;rlz-lalg-phenyl-ammom-l;l=lVr1)lVri2 C(=O)-N- carboxylic acid morpholino)-o=Sz- z ~3 z- r m=C~ NHjIVHz v a m .m v a a m r _p eny amino -C(=O)-N- carboxylic acid morpholino)-O-JUZ-~riz ~;ri3 ~riz-~:ri(-~;riz-~n-u-pnenyi ammom-~;t=~ryvriz C(=O)-N- carboxylic acid morpholino)-o-~uZ riz Sri, ~riZ pry-~riz-rnenyi-ammo carnoxyncm-~~=v~~riz N
C(=O)-N- acid morpholino)-o-~uz-Ntiz ~ri3 ~tiz-pry-caiZm-pneny-ammo m-~~=u~Nriz C(=O)-N- carboxylic acid morpholino)-O-lVZ-lVriz l:rig l;riz-l;ri(-l:riz-r-pnenyi-ammo m-~,~=~Jr~riz C(=O)-N- carboxylic acid morpholino)-o-~uz-mtiz ~;ti3 ~aiz-Lty-trtiz-Lri3-pnenyi-ammom-~;~=u~Ntiz C(=O)-N- carboxylic acid morpholino)-O-JUZ riz ~:ri3 ~;riz-~:ri(-~;riz-Sri; v-pnenyi-ammom-~,~=ulr~riz ~
C(=O)-N- carboxylic acid morpholino)-O-JUZ-1Vt12 1:ri3 uriz-~;ry-~riz-nn-u-pnenyi-ammom-~~=v~~riz C(=O)-N- carboxylic acid morpholino)-o-SOZ Hz CHj CHZ CH(-CHz-Methyl phenoxy-aceticm-(:(=NH)NHz N
C(=O)-N- acid ester morpholino)-o-SOz-NHz CH3 CHz-CH(-CHz-Methyl Cl-phenoxyaceticm-C;(=NH)NHz C(=O)-N- acid ester morpholino)-o-SOz-NHz CH3 CHz-CH(-CHzMethyl 1:-phenoxy-m-(:(=NH)NHz acetic C(=O)-N- acid ester morpholino)-o-~u2 Hz cai3 caiz ~;ti(-~aiz-Mecnyi ~tt3 pnenoxy-m-~:~=~ry~riz N
C(=O)-N- acetic acid ester morpholino)-o-~u~ Hz cai3 ~;ttz-jai(-caiz-Memyi ~ti3-u-pnenoxy-m-~:~=mry~riz N
C(=O)-N- acetic acid ester morpholino)-O-JVZ-iVri2 Lti, ~;tiz-t.ry-~riz-Memyt tsn-u-pnenoxym-l,(=lVt1)lVtlz C(=O)-N- acetic acid ester morpholino)-o-SOz-NHz CH3 CHz-CH(-CHz-Methyl Yhenoxyacehcm-C(=U)NHz C(=O)-N- acid ester morpholino)-o-SOz-NHz CH3 CHz-CH(-CHz-Methyl Cl-phenoxyacehcm-C(=U)NH_z C(=O)-N- acid ester morpholino)-o-SOz-NHz CH3 CHz-CH(-CHz-Methyl )~'-phenoxyaceticm-(:(=U)NHz C(=O)-N- acid ester morpholino)-o-~u2 tiz Lti3 ~aiz gay-~aiz-enemy ~ti3-pnenoxy-m-~;1=ul~riz N
C(=O)-N- acetic acid ester morpholino)-O-JVz-NriZ ~ti3 uriz-~:ry-urizMemyi ~ri3-u-pnenoxym-~~=a lr~riz C(=O)-N- acetic acid ester motpholino)-o-5uz-NHz Lti3 uriz-ury-~ry-Metnyi nn-u-pnenoxym-~~=~lr~tiz C(=O)-N- acetic acid ester morpholino)-o-z- z CH3 CHz-CH(-CHz-Phenoxyacehc m- z acid C(=O)-N-more o mo o-SUz-NHz CH3 CHZ-CH(-CHz-Cl-phenoxy-aceticm-C(=NH)NHz acid C(=O)-N-morpholino)-o-SUz-NHz CH; CHz-CH(-CHZF-phenoxy- aceticm-C;(=NH)NHz acid C(=O)-N-morpholino)-o-SUz-NHz CH3 CHz-CH(-CHZCH3-phenoxy-aceticm-C(=NH)NHz acid C(=O)-N-moipholino)-o-SOz NHz CH3 CHz CH(-CHz-CH3-U-phenoxy-aceticm-C(=NH)NHz C(=O)-N- acid morpholino)-o-SUz-NHz CH3 CHz-CH(-CHz-Bn-U-phenoxy m-C:(=NH)NHz acetic acid C(=O)-N-morpholino)-o-SOz-NHz CH3 CHz-CH(-CHz-Yhenoxyacehc m-C:(=U)NHz acid C(=O)-N-morpholino)-o- Oz-NHz CH3 CHz-CH(-CHz-Cl-phenoxyacehc m-t:(=U)NHz acid C(=O)-N-morpholino)-o-SOz-NHz CH3 CHz-CH(-CHzr-phenoxyacetic m-C;(=U)NHz acid C(=O)-N-morpholino)-o-SOz-NHz CH3 CHz-CH(-CHZCH3 phenoxy-aceticm-(:(=U)NHz acid C(=O)-N-morpholino)-o-SOZ-NHz CH; CHz-CH(-CHzCH3 U-phenoxy m-C(=U)NHz acetic C(=O)-N- acid morpholino)-o-SOz-NHz CH3 CHz-CH(-CHz-tan-U-phenoxy m-C:(=V)NHz acetic acid C(=O)-N-morpholino)-o-~u2 NHz C:H3 ~;Hz ~;H(-~aiz-rnenoxyemanol m-t,l=Nri)r~riz C(=O)-N-morpholino)-o-JUz-Nriz (.:H3 l;tlz-~atl-~atz-~;1-pnenoxy-emanoim-~;l=~ryririz C(=O)-N-morpholino)-O-JUz NHZ C:H3 l:Hz-l:Hl-lalz-r-prienOXy- eLllanolm-l;l=1Vri)iVtiz C(=O)-N-morpholino)-O-JU2-Ntl2 Lris ~'ri2-~-ril-~'riz'~-n3-pnenoxy-emanoim-~.l=mryvriz C(=O)-N-morpholino)-o-~uz-NHz ~ri3 ~riz-~ry-~ri2-~-ti3-v-pnenoxy-eman0lm-Ll=lVri)lVriz C(=O)-N-morpholino)-o-~uz-NHz ~;H3 ~;tlz ~ail-Lty-tsn-u-pnenoxy m-~:l=mryvri2 emanot C(=O)-N-morpholino)-O-JVZ-NHZ LH3 ~;tizw;til-~tiz-rnenoxyemanoi m-~l=u)~ri2 C(=O)-N-morpholino)-o-~u2-NHz LH3 ~alz-fail-LHz-~a-pnenoxyemanolm-~l=V)ivriz C(=O)-N-morpholino)-o-~uz NHz ~:H3 ~ai2-Ltil-t,tiz-r-pnenoxy-emanoim-Ll=u~~riz C(=O)-N-morpholino)-o- z- 2 3 2- z- 3-p epoxy=a ano m- =O NHz morpholino)-o-~uz-Nriz tai, c:riz-c:nl-~riz-Lna-u-Pnenoxy- m-~:l=u)r~riz emanoi C(=O)-N-morpholino)-O-JUZ-Ntlz c:ri3 Lriz-Lnl-Lriz-~n-u-pnenoxy- m-ul=u)Ntiz emanoi C(=O)-N-morpholino)-O-JVZ-Nriz c:rij caiz-tail-t,tiz-Memyt pnenoxy-emyim-t.l=mti)~tiz C(=O)-N- ether morpholino)-O-lVz-Ntiz 1x13 1x12-l;ril-l;riz-enemy ca-pnenoxyemym-i:l=mriJ~riz C(=O)-N- ether morpholino)-o-DVz-Nriz c:ri3 Ltiz Ltil-caiz-nnemyi r-pnenoxy-emyim-c:l=wri)wriz C(=O)-N- ether morpholino)-o-JVz-Nriz c;ti; ~aiz-tail-caiz-Memy c:ri3 pnenoxy-m-c:l=~ri)~riz C(=O)-N- ethyl ether morpholino)-o-JUz ivtiz cai3 ~a12-tail-~;tiz-Memyi c:rt3-u-pnenoxy-m-~;l=ivri)Ntiz C(=O)-N- ethyl ether morpholino)-o-JVz-Ntiz c:ri3 caiz-cail-caiz-enemy tsn-u-pnenoxym-c.l=mri)r~riz C(=O)-N- ethyl ether morpholino)-o-5uz lvtiz cai3 uttz-uty-catzMemyi rnenoxyemyim-c:l=u)wriz C(=O)-N- ether morpholino)-o-~uz-lvtiz t;tt3 cai2 c:ril-LtizMemyi ca-pnenoxyemyim-c:l=u)r~tiz C(=O)-N- ether morpholino)-o-JUz-Nriz ~;ti3 caiz-tail-caiz-Memyi r-pnenoxyemyim-~:l=u)ivriz C(=O)-N- ether morpholino)-o-JUz-lVri2 1x13 1x12-lJtil-l:rlz-Memy1 t;tt3- m-t;l=u)iVrl2 C(=O)-N- phenoxyethyl ether morpholino)-O-JUz-lVriz Lti3 caiz tail-caiz-nnemyi ~ti3-u- m-~:l=u)r~riz C(=O)-N- phenoxyethyl ether morpholino)-o-~uz tvtiz c:ti3 ~:riz-c:ril-caiz-enemy rsn-u- m-c:l=u)mriz C(=O)-N- phenoxyethyl ether morpholino)-o-JUz-Nriz cai3 r z- P enY m- z CHz-S(O)z-CH3 O-JUz-Nriz s z- z- -p eny m- z CHz-S(O)z-CH3 O-JUZ-Ntl2 cat, catz-~:ril-caiz-r-pnenyt m-t,l=wri)~riz CHz S(O)z-CH3 o-~uz-Nttz tai, c:riz-c.ril-c:riz-~ti3-pnenyi m- z CHz-S(O)z-CH3 o-~uz-tvttz c,ti3 uriz-aril-c:rizc:ri3-u-pneny m-~l=mti)mriz CHz-S(O)z-CH3 o- z- z s z- z- n- -p eny m- z CHz-S(O)z-CH3 O-JUz-Nri2 cai3 c:riz-~:ril-uriz-pnenyi m-~l=u)wriz CHz-S(O)z-CH3 o-JU2-Ntlz 1.113 ljtlz-fail-lalz-(_:1-prienyl m-t=l=u)lVtiz CHz S(O)z-CH3 o-~uz Nriz tai, c:riz-c:ril-~rizr-pnenyi m-c:l=u)wriz CHz-S(O)z-CHj 1\ 1i-J
o-r z s r z- 3-p m- z enY
CHz-S(O)rCH3 o-JUz Hz 3 z- z- s- m- z N -p enY
CHz-S(O)z o-SUz-NHx 3 r z- n- m- x -p eny CHz-S(O)z-CH3 o-SUx-NHx C:H3 (:Hx-fail-C:Hx-Anllme p-l:l=1Vri)lVtlx CHz-S(O)z-CH3 o-SVZ Hx LH3 LHz LHl-~Hz_-am p- z N me CHz-S(O)z-CH3 o-SUZ Hx C;ri~ C:Hx-(.;Hl-c:Hx_-and p- x N me CHz-S(O)z o-SUx-NHz LH3 c:H2 LHl-c:Hz-3-am p- z me CHx-S(O)x-CH3 o-SUz Hx 1:H3 C:Hx-l;Hl-l;Hz1:H3 p- x N U-arillme CHx-S(O)z-CH3 o-JUx-NHx 1;H3 C:Hx-l;Hl-l;Hx-t5n-V-arillme p- x CHz-S(O)z-CH3 o-JUx-NHx 1:H3 lair-~atl-l:tix-Anllme p- x CHz-S(O)z-CH3 o-JVx-NHx 1;H3 lair-fail-~alx-t:1-anlnne p- x CHz-S(O)z-CH3 o-~Vx-NHx CJH3 l:Hz l:Hl-l;Hz_-am p- x me CHz-S(O)rCH3 o-JUx-NHx C:H3 i x- 3-am p- x me CHz-S(O)z-CH3 o-5Ux-Nriz s r r 3- p- x -am a CHz S(O)z-CH3 o-~Uz-Nrix 1;H3 l:Hx-l:Hl-l:Hx-ri_ p- x -an1 me CHx-S(O)z-CH3 o-~Vz-NHz ~:H3 LtlzW allW eny m- z a1z- -ammo-car oxy is CHI S(O)z-CH,acid o-5Uz Hz c:H3 LHz-t.Hl-LHZeny m- z N -ammo CHz-S(O)z-CH,carboxylic acid O-~Vx-NHx ~:H3 Ltizmay-Ltiz-r-pnenyi-ammo m-~;~=mryvriz CHz-S(O)z-CHjcarboxylic acid O-JVx-NHx 1:H3 l;Hx-l;Hl-(.;Hx-1;t13-pnenyl-ammo m-lj(=lvri)lvttx CHz-S(O)z-CH3carboxylic acid o-5uz-NHx c~H3 LHx-~;Hl-~;Hz-~:ri,-u-pnenyi m-t,l=mryvrix ammo CHx-S(O)x-CH,carboxylic acid o-5Ux-NHx C:H3 l:Hz l:Hl-l;Hx-t5n-V-prienyl m- x ammo CHz-S(O)z carboxylic CH3 acid o-~u2 Hx LH3 uHx-~Hl-uriz-rnenyi-ammo m-~~=~~wriz N carnoxync CHz S(O)z acid o-5Uz Hx c:H3 ~:HZ c:Hl-t.Hz-~a-pnenyi-ammo m-~l=vyvrix N
CHx-S(O)z-CH3carboxylic acid o-z- z s z- z- -p m- z eny -ammo CHz S(O)z-CH3carboxylic acid O-5U2 Hx C:H3 l.:Hx-l;Hl-l:Hx-1;H3 m-l;l=U)iVrix N pneriyl-ammo CHz-S(O)x-CH3carboxylic acid o-~u2 Hz ~:H3 t_;tiz-~tyu;tizw;ri3 m- x N m-pnenyi-ammo CHz S(O)z carboxylic CH3 acid o-~uz-NHx LH, LHZ c:Hl-MHz-tsn-u-pnenyi-ammo m- z CHz S(O)x-CH3carboxylic acid o-SOx-NHz CH3 CHz-CH(-CHz-Methyl m-C(=NH)NHz phenoxy-acetic CHz S(O)z acid CH3 ester o-SOz Hx CH3 CHZ CH(-CHx-Methyl m-C(=NH)NHz N Cl-phenoxyacehc CHz S(O)z-CH3acid ester o-SOx-NHx CH3 CHz-CH(-CHz-Methyl m- z r-phenoxy-acetic CHz S(O)Z acid CH3 ester o-tux-NHx ~ai3 taiz-t_;ttl-~tiz-Memym;ri3-pnenoxy- m- z CHz-S(O)x-CH3acetic acid ester o- z- z a z- z- et y 3- -p epoxy-m-CHz-S(O)z-CH3acetic acid ester o-~uz Ntiz ~n3 Ltiz-qty-~aiz-Metnyi tsn-u-pnenoxym- z CHz-S(O)z-CH,acetic acid ester o- z- z CHs z- z- a y enoxyacehc m- z CHz-S(O)z-CH,acid ester o- Z z CH3 CHz-CH(-CHz-Methyl Cl-phenoxyacehcm-C(=U)I
HZ
CHz-S(O)z-CH3acid ester o- Z z - CH3 z- z- a y -p enoxyacehcm- z J V 1 '111 CHz-S(O)z-CH3acid ester o-JUZ-Nri2 Ln3 ~:nz-~nl-~;nz-Memy ~n3-pnenoxy-m-~;l=vyvnz CHz S(O)Z acetic acid ester CHj O-JVZ-Nti2 Lti, ~aiz-~nl-~nz-a Y s- -p epoxy m- z CHz-S(O)z-CH3acetic acid ester o-~uz-ivnz Ln3 trnz-~ryu:nz-memyi isn-u-pnenoxym-~.l=vyvnz CHz-S(O)z-CH3acetic acid ester o-SOz-NHz CHj CHz-CH(-CHz-Yhenoxyacehc m-C(=NH)NHz acid CHz-S(O)z-CH3 o-SOz-NHz CH3 CHz-CH(-CHz-Cl-phenoxy-acehcm-C(=NH)NHz acid CHz-S(O)z-CH3 o-SOz-NHz CH3 CHz-CH(-CHz-1~-phenoxy- aceticm-(:(=NH)NHz acid CHz-S(O)z-CH3 o-SOz-NHz CH3 CHz-CH(-CHz-CH3 phenoxy-acehcm-C(=NH)NHz acid CHz-S(O)rCH3 o-S02 NHz CH3 CHz-CH(-CHz-3- -p epoxy-acehcm- z CHz-S(O)z-CH3acid o-SOZ NHz CH3 CHz-CH(-CHzn- -p epoxy acehcm- z aci CHz-S(O)z-CH3 o-SOz-NHz CH3 CHz-CH(-CHz-Yhenoxyacehc m- z acid CHz-S(O)z-CH3 o-SOZ-NHz CH3 z- Z -p enoxyacehc m- z aci CHz-S(O)z-CH3 o-SOz NHz CH, z- z- -p enoxyacehc m- z aci CHz-S(O)z-CH3 o-SUz-NHZ CH3 CHz-CH(-CHz-CH3 phenoxy-acehcm-(:(=U)NHz acid CHz-S(O)z-CH3 o-SOZ-NHz CH3 CHz-CH(-CHz-3 -p epoxy acehcm- z CHz-S(O)z-CH3acid o-SOz-NHz s r r n- -p epoxy acehcm- z aci CHz-S(O)z-CH3 o-~uz-Ntiz uti, utiz-~nl-~nz-rnenoxyemanoi m-~;(=wn)wnz CHz-S(O)z-CH3 O-JVZ-Nriz Lti3 ~tiz-~ry-~nz-m-pnenoxy-emanoim- z CHz-S(O)z-CH3 O-JUy-1Vt12 Lti3 unz-~nl-~nz-r-pnenoxy- emanoim-~l=wn~wnz CHz-S(O)z-CH3 o-~uz-Ntiz un3 unz-~nl-~nz-~n3-pnenoxy-emanoim-~l=mn~wn2 CHz-S(O)z-CH3 o-JVZ-lVriz ~:n3 ~nz-~nlw;nzw:n3-u-pnenoxy-emanoim-~:l=~n~~nz CHz-S(O)z O-JUz-Nnz ~:n3 ~-riz-~nl-~nz-~n-~-pnenoxy m-~,l=mnyvnz emanoi CHI S(O)z O-JVz-Nri2 ~n3 ~nz-~nl-~nz-enoxye ano m- z CHz S(O)z-CH3 O-JUz-Nnz Lri3 L'ri2-L'ril-L'ri2--p enoxye ano m- z CHZ S(O)z-CH3 o-~uz-Nnz uti3 ~nz-~nl-unz-r-pnenoxy-emanoim-~l=u~wnz CHz-S(O)z-CH3 o- z- z s z- z- 3-p epoxy-a ano m- z CHz-S(O)z-CH3 o-JVz 1Vr12 1.t13 ~-nr~-nl-~nz-~-ris-~-pnenoxy-m-~:l=vyvnz emanoi CHz-S(O)z-CH3 o- z- z a z- z- n- -p enoxy- m-~l=V~Nriz a ano CHz-S(O)z-CH3 O-JUz-Ntlz Lti3 caiz-~til-caiz-iviemyi pnenoxy-emyim-~l=Nri~Nriz CHz-S(O)z-CH,ether O-JUz-Nriz Lti3 ~tiz-~til-Lti?iviemyi m-pnenoxyemyim- z CHz-S(O)z-CH,ether o-~uz-Nttz ~a13 caiz-~;til-~;riz-iviemyi r-pnenoxy-etnyim- z CHz-S(O)z-CH,ether o-5uz-Nrlz c.;ti3 Ltiz-Ltil-Ltiz-iviemyi Lti3-pnenoxy-m- z CHz-S(O)z-CH3ethyl ether O-~uz-Nriz Lti3 ~ttz-~til-~tiz-ivietnyi ~ri3-V-pnenoxy-m- z CHz-S(O)z-CH,ethyl ether o-JUz-Nttz cal3 z- ~ a y n- _p enoxy m- z CHz S(O)z-CH3ethyl ether O-JUZ-Ntlz ~a13 z- r a y enoxye y m- z CHz S(O)z-CH3ether O-JVz-Nriz l~tij z- z- a y -p enoxye m- z y CHI S(O)z-CH,ether O-JUz-Ntiz ~ai3 Ltiz-t,til-Ltiz-ivietnyi r-pnenoxyemyim-~,l=uyvriz CHz-S(O)z-CH,ether o-JUz-Ntiz 1;t13 laiz-fail-l:rlz-nnecnym;ri3- m- z CHz S(O)z-CH3phenoxyethyl ether O-JVz-Ntlz l;tl3 l;tlz-fall-(alz-lVleTilyi 1jt13-u-m-l;l=V)lVriz CHz-S(O)z-CH3phenoxyethyl ether o-JU2 Nttz ~ai3 Lti2 ~;til-t;tiz-miemyi tsn-V- m-~l=vyvriz CHz-S(O)Z phenoxyethyl CH, ether o-~u2 Ntlz Lti3 cai2 Ltil-~tiz-pnenyi m-~l=Nri~Nriz hexane)-o-~uz Ntiz Lti, ~tiz ~ttl-~riz-~i-pnenyi m- z hexane)-O-JVy-Ntiz 1x13 laiz-fall-l:riz-r-pnenyi m- z hexane)-O-JUz-NHz 1;ri3 lalz-fail-lalz-3 p eriy m- z hexane)-O-JVz-Ntiz lal3 lalz-fall-l:riz-1x13 u-pnenyi m- z .
hexane)-o-JVz-Ntlz l;tl3 z- z- n- -p eny m- z hexane)-O-JUZ-NtiZ 3 r r P enY m- z hexane)-o-~uz Ntlz s z- z- -p eny m- z hexane)-O-JUz-Nriz , 2- z- -p eny m- z hexane)-o-auz-Ntiz ~ai3 Ltl2 pail-~tiz-~:ri~-pnenyi m-~l=vyvriz hexane)-o-~u2 NtiZ 1x13 z z- 3- -p eriy m- z hexane)-o-~uz Ntiz uti3 ~riz uril-~riz-rsn-v-pnenyi m- z hexane)-o-~u2 Nriz l;ri, l.atz-~;til-~;ttz-Aniime p-~:l=mtiyvrtz hexane)-O-JUz-Ntiz ltij l:riz-l:ril-l.rizl;i-amime p-l;l=lVr1)lvriz hexane)-O-JUz-Niiz ~-ri3 ~-ri2-~-ril-~'ri2-r-anllme p-1.1=lvri)lVtiz hexane)-o-~uz-Ntiz ~ti3 ~tiz tail-~riz-~:ri3-aniime p-~l=Nriyvriz hexane)-O-lUz-Ntlz lalg l;tlz-l;tll-l:riz-C.ri3 u-anlllllep-l;l=lVriJlvriz hexane)-O-JUz-Nriz 3 z- z- n- -am me p- z hexane)-o-z- z s z- z- m me p- z u' V~111 hexane)-O-JUZ-NHZ C;H3 l;Hz-l:H(-l;Hz-l:l-amlme p-l;(=V)Nrlz hexane)-o-~Uz-Nriz l,ti3 (.,HZ-t,H(-I.HZ-r-amime p- z hexane)-o-~uz-NHz c:ri3 ~tiz-Sri(-~HZ- ~ti3-amime p-~(=u)Nriz hexane)-o-JUz-NHz ~H3 MHz rlz-~H3-u-amime p-~(=u)Nriz ~H(-~
hexane)-O-JUz-NHz 1:H3 l;tlz-lal(-lalz-t5ri-u-anllme p-l:(=U)NHz hexane)-o-JUz-NHz ~;H3 t.Hz-c:H(W;Hz-rneny-ammo-carooxyucm- z hexane)- acid o-~Uz Hz LH3 uHz-uri(-utiz-m-rnenyi-ammo m-~(=Nri)Nriz N
hexane)- carboxylic acid O-JUz Hz c:H3 MHz-~H(-~HZ- r-pnenyi-ammo m- z N
hexane)- carboxylic acid o-JVz-NHz ~;H3 ~:rtz-~:r1(-~;tiz-j-p eny -ammo m- z hexane)- carboxylic acid o-~u2 Hz ~;H3 ~:Hz-~:H(-~;H2 3- -p eny ammo m- z N
hexane)- carboxylic acid o-~Uz-NHz c:H3 LHz-LH(-Ltiz-tsn-u-pnenyi m- z ammo hexane)- carboxylic acid o-5Uz-NHz c:H3 ~ttz-~Hl-~HZ- eny -ammo car m- z oxy is hexane)- acid o-5Uz-NHz (:H3 c:Hz-LH(-LHZ- ~a-pnenyl-ammo m- z hexane)- carboxylic acid O-5Uz-NHZ C;H3 (:HZ-l:H(-laiz-r-prieriyl-ammo m-hexane)- carboxylic acid o-5V~ Hz t;H3 c:Hz-LH(-LHZ ~t13-pnenyl-ammom- z N
hexane)- carboxylic acid o-5Vy-NHy C:H~ C;ri2-l:ri(-lalz-1:H3-u-pnenyl-ammom-l:(=V)Nriz hexane)- carboxylic acid O-JVZ-NHZ C:H3 C:Hy-l:H(-lal2-tSn-V-prieriyl-ammom-hexane)- carboxylic acid o-z-NHz CH3 CHZ Hz- Methyl phenoxy-aceticm-C(=NH)NHz CH(-C
hexane)- acid ester o-SOz-NHz CH3 CHz-CH(-CHz- Methyl Cl-phenoxyacehcm-(:(=NH)NHz hexane)- acid ester ~-~z Hz ~3 CHz-CH(-CHz- a y _p enoxy- m- z N acetic hexane)- acid ester o-5Uz-NHz ~:H3 LHZ-~H(-~tiz-Metnym:H3 pnenoxy-m- z hexane)- acetic acid ester o-JUZ Hz C:Hj lalz-l:H(-lalz-lVieLnyl l=rig-U-pnenOXy-m- y N
hexane)- acetic acid ester o-~Vz Hz C:H3 lalz-l:H(-l:Hz-a y n_ -p enoxy m- z N
hexane)- acetic acid ester o-r z 3 - CHz-CH(-CHz- a y enoxyacehc m- z hexane)- acid ester o-SOz-NHz CHj CHz-CH(-CHz- Methyl Cl-phenoxyacehcm- z hexane)- acid ester o-z- z j CHz-CH(-CHz- Methyl r'-phenoxyacehcm- z hexane)- acid ester o-5U2 Hz t;H3 MHz-~H(-~HZ- nnemyi ~H3-pnenoxy-m- z N
hexane)- acetic acid ester o-~Uz-NHZ t;H3 LHz-~H(-~riz-Metnyi ~H,-u-pnenoxym-~(=u)mriz hexane)- acetic acid ester o-JUz-NHZ C:H3 1x12-l;tl(-C;tl2-Methyl tSn-u-prienOXym-l:(=V)lVri2 hexane)- acetic acid ester o-z-NHz CHj CHz-CH(-CHz- Yhenoxyacehc m-(:(=NH)NHz acid hexane)-o-2- Z a z- z- -p epoxy-aceric aci v~ a.aa~.a m-hexane)-o-r z 3 z- z- -p epoxy- aceticink(--~NHz acid--.- ..
hexane)-o-z- z CH3 CHz-CH(-CHz- CH3 phenoxy-aceticm-C(=NH)NHz acid hexane)-- z- 2 3 2- r 3- -p epoxy-aceticm-hexane)- acid o-z- z s z-CH(-CHz- Bn-O-phenoxy m-(:(=NH)NHz acetic acid hexane)-o-z- z -CHj -CHz-CH(-CHz- enoxyacehc aci m- z -hexane)-o-z- z CHj CHz-CH(-CHz- -p enoxyacehc m- z aci hexane)-o-SOz-NHz CH3 CHz-CH(-CHz- r'-phenoxyacehc m- z acid hexane)-o-z- z 3 CHz-CH(-CHZ CH3-phenoxy-aceticm-C(=U)NHz acid hexane)-o-z- z CH3 CHz-CH(-CHz- CH3-U-phenoxy m- z acetic hexane)- acid o-z- z CH3 CHz-CH(-CHz- Bn-U-phenoxy m- z acetic acid hexane)-o-~uz-Ntiz ~;t13 ~alz-Lnl-~alZ enoxye ano m- z hexane)-O-JVz-Nt12 lai3 l;riz-fall-l:riz--p eriOXy-a ano m-hexane)-o-JVz-Nriz ~;ri, Lnz-Lnl-~:n~ r-pnenoxy- emanoim-~l=ivn)ivnz hexane)-o-z- z s z z- 3-p epoxy-a ano m- z hexane)-O-JUz-Nri2 Lti, cay-~nl-~nz- ~n3-~-pnenoxy-emanoim-~l=ivn)ivnz hexane)-O-~uz-NHz , z z- n- -p epoxy a m- z ano hexane)-o-~u2 Hz cal3 r z- enoxye ano m- z N
hexane)-O-JVz Hz C;tl3 1:ri2-l:ril-l:riz-l;1-pnenOXyeiilan0lm-l;l=V)iVriz N
hexane)-o-~Vz Hz Ltl3 Lttz-l:tllWaiz-r-pnenoxy-etnanolm- z N
hexane)-o-JVz-lVriz ~n3 ~nz-~nl-~rir 3-p epoxy-a ano m-hexane)-O-JVZ nz Lti3 ~ttz-urll-~nz- aria-~-Pnenoxy- m-~l=v)ivnz w emanoi hexane)-o-~uz-Ntiz Lti3 ~nz-~nl-~nz tsn-u-pnenoxy- m-~l=u)mn2 emanoi hexane)-o-JUz-Nriz ~ti3 ~nz-unl-~n2- iviemyi pnenoxy-emyim-~l=rVn)wnZ
hexane)- ether o-~uz-wtiz cai3 ~nz-unlw;nz-nnemym-pnenoxyemym-hexane)- ether O-JU2-NHz cai3 c:n2-~nl-~ti2-enemy r-pnenoxy-emyim-hexane)- ether O-JUz t12 l;tl3 z' y- a Y 3-p epoxy- m- z hexane)- ethyl ether o-~uz-Ntiz Lti, z- z- a y 3- -p epoxy-m- z hexane)- ethyl ether o-JUZ-iVriz Lri3 Lri2-Lril-L'ri2-Memyi rsn-v-pnenoxym-~;l=ivn)ivnz hexane)- ethyl ether o-5Uz-Ntl2 l;Hj lalz-~:ril-laiz-enemy rnenoxyemyim-~;l=V)ivnz hexane)- ether O-JUz-Ntl2 Ltij ~:nz-Lnl-Lnz- a y -p enoxye m- z y hexane)- ether o-z- z s z- z- a n-C(=O)I~Z
y ,-phenoxyey hexane)- ether o-~uz-Nriz lal3 lalz lal(-lalz-lvieulyl m- z l:ri3-hexane)- phenoxyethyl ether o-~u~ tiz cal, lalz-lal(-lalz-l viemyl l:rij-u-m-~(=v)Nrlz N
hexane)- phenoxyethyl ether o-JVZ t12 C;tl3 lily-l;ti(-laiZ- Mettlyl tSn-v- m-N
hexane)- phenoxyethyl ether o-JUZ-Ntiz Cai3 l:Hi-l.al(-1x12-pneriyl m-(HO-phenyl))-.
O-5Vi-NHz 1x13 1x12-l;tl(-laiz_-p m-eny (HO-phenyl))-o-~VZ tlz 1a13 calz c:tl(-l:riz_-p m- z N eny (HO-phenyl))-O-JUZ-Nt12 1a13 calz-c:rl(-~riz-l:rl3-phenyl m- z (HO-phenyl))-O-JUZ-Ntiz 1;ri3 1;t12-C:ri(-l;riz-3 m--p eriy (HO-phenyl))-O-~Uz-Nriz lal3 l:rlz-l:rl(-l:rlz-rsn-V-phenyl m- z (HO-phenyl))-o-~u2 tiz 1a1, calz cal(-l:rlz-phenyl m- z N
(HO-phenyl))-O-~Uz-Nriz 1a1, l:riz-l:rl(-l:rlz-la-phenyl m- z (HO-phenyl))-O-JVZ-Ntlz 1;t13 Calz-Cal(-lainr-phenyl m-l:(=U)Nrl2 (HO-phenyl))-O-JVZ-Nt12 1.;ri3 1x12-lai(-1:112-1.:ri3-phenyl m-(HO-phenyl))-O-JU2-Nriz 1;ri3 l;tl2-lai(-l.;riy-3- m--p eriy (HO-phenyl))-O-~Uz-Nriz lai3 z z- n- m- z -p eny (HO-phenyl))-o-5Vz-Nriz llH3 z 2- m p-me (HO-phenyl))-o-JUz-Nriz t_;ri3 lalz-lal(-c:rizl:l-amlme p-~(=lvrl)mrlz (HO-phenyl))-o-5U2-Nriz (a13 Z- 2- -am p-me (HO-phenyl))-O-JVZ-NHZ laij lily-Cai(-1x12-1x13-anllllle p-l,(=lVti)lVrlz (HO-phenyl))-O-JU2-Nriz 1x13 l:riz-l;ri(-l:riZ-3_ p-_aril me (HO-phenyl))-o-~u2 HZ lai3 laiz-l;ri(-l;riZ-n_ p-N -aril me (HO-phenyl))-O-JUz-NtiZ 1x13 l:riy-11-1(-1x12-Arillme p- y (HO-phenyl))-O-JUZ-NH2 1;t13 lily-lal(-1x12-(:l-amlme p-l;(=U)Nrl2 (HO-phenyl))-O-JUZ-Nri2 1:113 lily-l:rl(-l:rlZ-r-anllme p-l:(=V)1Vr12 (HO-phenyl))-o-~uz-Nrlz l:ri3 l:rlz-l:ry-l;riz-l:ri3-anllme p-1.(=u)l~nz (HO-phenyl))-O-JU2-Nt12 lalj l:tlZ Cal(-l.;riZ-l:rig-v-arillllle p-l:(=U)lVtiz (HO-phenyl))-O-JUz t12 laig lily-l;ri(-1:ri2-liri-u-anllllle p-L(=V)lVriz N
(HO-phenyl))-o-~urNttz lai, ~nr~-Hl-~-nz-rnenyl-amino-carooxync m-1:(=l~ri)l~riz (HO-phenyl))-acid o-~Uz-Ntlz l:rij laiz-l:rl(-l:tlzeny m- z -ammo (HO-phenyl))-carboxylic acid o-~uz-Ntiz 3 z- z- -p m- z eny -ammo (HO-phenyl))-carboxylic acid = 160 -o- z- z s z- z- 3-p m-eny -ammo ,...
..
(HO-phenyl))-carboxylic acid o-5Vz-NHz C:H3 (:Hz-LH(-(:Hz-C:H3-V-pnenyl m-tr(=lvrl)lvriz ammo (HO-phenyl))-carboxylic acid o-SUB NHz CH3 C:Hz-C:H(-C;Hz-tin-U-phenyl m-L(=NH)NHz ammo (HO-phenyl))-carboxylic acid o-5Uz NHz C:H3 l:Hrl;H(-l:Hz-Ynenyl-ammo m-l:(=u)lvrlz caruoxync (HO-phenyl))-acid O-JUZ-NHZ 1:H3 I:HZ-l;ri(-l:Hz-l;l-prienyl-ammo m-(HO-phenyl))-carboxylic acid O-SUZ-NHZ (:H3 l:Hz-C;H(-l;Hzr-prieriyl-ammo m- . z (HO-phenyl))-carboxylic acid o-5Uz-NHz t;H, LHz-c:H(-LHi~ri3-pnenyi-ammo m- z (HO-phenyl))-carboxylic acid o-SUZ NHz C:H3 Ltlz-LH(-Ltiz-LH3-u-pnenyl-ammo m- z (HO-phenyl))-carboxylic acid o-5Uz NHz C:H3 l;tlz-C:H(-l:Hzn- m--p eny -ammo (HO-phenyl))-carboxylic acid o- z- z CH3 CHi CH(-CHz-a m- z y p epoxy-acetic (HO-phenyl))-acid ester o- r z 3 CHz-CH(-CHz-a m- z y -p enoxyacehc (HO-phenyl))-acid ester o- z- z z- z- a m- z ~,~. y s -p epoxy-acetic (HO-phenyl))-acid ester o-5U2-NHZ c:H3 MHz LH(-~riz-enemy m-~~=mri)mriz ~ri3-pnenoxy-(HO-phenyl))-acetic acid ester o-SUZ-NHZ (a13 1:H2-C;H(-laiZ-MemyW m- z a1,-u-pnenoxy-(HO-phenyl))-acetic acid ester O-5V2-NHZ c:H3 LHz-Lti(-LHz-Memyi m-~(=wri)rrriz tsn-u-pnenoxy (HO-phenyl))-acetic acid ester o- z- z - CFI3 CHz CH(-CHz-Methyl m- z Yhenoxyacetic (HO-phenyl))-acid ester o- O~ N~ CH3 CHz-CH(-CHz-Methyl m- z Cl-phenoxyacehc (HO-phenyl))-acid ester o- Oz-NHz CH3 CHz-CH(-CHz-Methyl m- z J'-phenoxyaceric (HO-phenyl))-acid ester o-5Vz-NHz c:H3 LHz-LH(-~HZ-nnetnyi m- z ~rij-pnenoxy-(HO-phenyl))-acetic acid ester o-5UZ NHz LH, LHz-Lti(-LHz-Metnyi m- z ~ri3-v-pnenoxy (HO-phenyl))-acetic acid ester o-5uz-NHz c:H3 LHzw:Hl-~nz-enemy m-~~=v)mriz tsn-u-pnenoxy (HO-phenyl))-acetic acid ester o- z- z - CH3 CHz CH(-CHz-Yhenoxyacehc m- z acid (HO-phenyl))-o- Z z - CH3 CHz-CH(-CHz--p m- z epoxy-acetic aci (HO-phenyl))-o- Z z - CH, CHz-CH(-CHz--p m- z epoxy-acetic aci (HO-phenyl))-o- z- z ~-- CHz-CH(-CHz-3-p m- z epoxy-acetic aci (HO-phenyl))-o-SOz-NHz CH3 CHz-CH(-CHz-CH3-U-phenoxy-acetic m-C(=NH)NHz (HO-phenyl))-acid o-SOz-NHz CH3 CHz-CH(-CHz-13n-U-phenoxy m- z acetic acid (HO-phenyl))-o-SOZ NFIz CH3 CHz-CH(-CHz-Yhenoxyacehc m-C(=U)NHz acid (HO-phenyl))-o-SOz-NHz CH3 CHz-CH(-CHz-Cl-phenoxyacehc m-C(=U)NHz acid (HO-phenyl))-o-SOz-NHz CH3 CHz-CH(-CHz-F-phenoxyacehc m-C(=U)NHz acid (HO-phenyl))-o-SOZ NHz CH3 CHz-CH(-CHz-CH3-phenoxy-acetic m-(:(=U)NHz acid (HO-phenyl))-o-z- z 3 z- z- 3- m-C;(=U)NHz -p epoxy acetic (HO-phenyl))-acid o-50z-NFIz CH3 CHZ CH(-CHz-Bn-U-phenoxy m-C:(=U)NHz acetic acid (HO-phenyl))-O-JUz-NHZ cal3 ~:rlz-~ril-~riz-enoxye m- z ano (HO-phenyl))-O-~Vz-Nriz lal3 c:Hz-fall-lalz-l:l-pnenoxy-emanol m- z (HO-phenyl))-o-~Vz-Nriz lal3 call-call-l;tlz-r-pnenoxy- m-l:l=lvrl)wrlz emanol (HO-phenyl))-O-JVZ-NH2 cal3 lalz-fall-Ltlz-l:rl3-pnenoxy-emanol m-l:l=lvrl)wrlz (HO-phenyl))-o-JUz rlz lal3 l:rlz-fall-~;rizl:rl3-v-pnenoxy-emanoi m-t;l=lrrl)ivrlz iv (HO-phenyl))-O-JVZ-Nri2 c~ri3 lalz-lall-l;tlz-tsn-V-pnenoxy m-~;l=lvrl)wrlz emanol (HO-phenyl))-O-JUZ-NHZ cal3 ~riz-~ril-~riz-rnenoxyemanol m-~l=u)wrlz (HO-phenyl))-o-~uz-Nriz l:rl3 l:rlz-l:rll-l:rlz-l:l-pnenoxyemanoi m-l:l=u)mrlz (HO-phenyl))-o-auz-NHz lal3 l:rlz-l:rll-l:rlz-r-pnenoxy-emanol m- z .
(HO-phenyl))-o-JVZ Hz lal3 lalz-call-l:rlz-~ri3-pnenoxy-emanol m-l:l=v)lrrlz N
(HO-phenyl))-O-JVz H2 C:ri3 lalz-lall-l;tlzj- m-N -p epoxy-a ano (HO-phenyl))-o-5VZ-Nriz , z Z- n- m- z -p epoxy-a ano (HO-phenyl))-o-JUZ-Nriz cal3 l;tlz Ltll-calz-ivleulyi m-l.l=ivrl)ivrlz pnenoxy-emyl (HO-phenyl))-ether O-JUZ-Nri2 c:H3 lalz Ltll-calz-ivleulyi m- z l:l-pnenoxyemyi (HO-phenyl))-ether O-JUZ-NH2 cal3 ~riz-~nl-~nz-ivlernyl m- z r-pnenoxy-emyi (HO-phenyl))-ether O-JUZ-NHZ cal3 lalz-fall-lalz-lvlemyl m- z ~ri3-pnenoxy-(HO-phenyl))-ethyl ether o-JUZ-Nriz cal3 lalz-fall-lalz-tvlemyllal3-v-pnenoxy- m-l:l=lvrl)ivrlz (HO-phenyl))-ethyl ether o-z z a i r a m- z y n--p epoxy (HO-phenyl))-ethyl ether o-~u2 Hz Cal3 latz-l:rll-l:rlz-Memyl m-t,l=u)lvtlz N rnenoxyemyl (HO-phenyl))-ether o-~uz-Ntlz cal3 ~riz-~ril-~rizivlemyll:l-pnenoxyemyl m-l:l=V)mrlz (HO-phenyl))-ether o-~uz-Ntlz cal3 ~riz-~ry-~nz-ivleulyl m-l.;l=u)mrlz r-pnenoxyemyl (HO-phenyl))-ether o-~uz-NHZ Cal3 lahlail-lirlz-Mettlyll:rlj- m-(HO-phenyl))- phenoxyethyl ether O-JUZ-NHZ 1:ri3 1;ri2-fail-lily- MeLllyll;rij-V-m-(HO-phenyl))- phenoxyethyl ether O-JUz-Ntlz cal, lalz-l:rll-l:rlz- a y n- m- z (HO-phenyl))-phenoxyethyl ether O-JUZ-1Vt12 lal3 z- z- P m- z enY
(Cl-phenyl))-o-JUz-NHz Cal3 z- 2- -p m- z eny (Cl-phenyl))-o-~uz-Ntiz cal3 l:rlz-l:rll-l:rlz-r-pnenyl m-l.l=wrl)mrlz (Cl-phenyl))-O-JVZ-NHZ 1:ri3 laiz-fall-lal2-l:rl3-prienyl m-(Cl-phenyl))-O-JUz-lVHz 1x13 l:riz-fall-lal2-1:ri3-u-prieriyl m-(Cl-phenyl))-= 162 -o- z- z s z- r n_ m--p enyl (Cl-phenyl))-o-~uz Nnz ~n3 ~nz-~nl-~nz-pnenyl m- z (Cl-phenyl))-o-~uz-Nnz , ~nz-c:nl-~nz_-p m- z eny (Cl-phenyl))-o-~uz Nri2 3 Y z- -p m- z eny (Cl-phenyl))-O-JVZ-Nriz 1x13 z- r 3-p m- z eny (Cl-phenyl))-o-~uz-Ntiz 1x13 Y z- 3- m- . z -p eny (Cl-phenyl))-O-JUz Nnz s z- r n- m- z -p eny (Cl-phenyl))-o-auz-Ntiz Lti3 Lnz-Lnl-Lnz-amime p-~l=mnyvnz (Cl-phenyl))-o-~uz Ntiz ~n3 ~nz-~nl-~nz-m-amime p-~l=mn~Nnz (Cl-phenyl))-O-JUZ-Nriy ~;n3 ~:nz-~:nl-tJnz-r-amime p-~.l=ivnyvnz (Cl-phenyl))-O-JUZ-Nri2 l;rlj 1:r12-l;rll-l;tlZ-~n3-amime p-~,l=ivnyvnz (Cl-phenyl))-O-JUZ-Ntl2 ~t~3 uti2 ~til-~nz-~n3 p-~l=Nn~Nnz u-amime (Cl-phenyl))-O-JUz-Nriz ~n3 ~nz-~nl-~riznn-u-amime p- z (Cl-phenyl))-o-~uz Ntiz ~:n3 ~;ttz-~nl-Lnz-amime p- z (Cl-phenyl))-o-JU2-Nri2 1:ri3 Y z- -ant p-me (Cl-phenyl))-o-JUz-Nriz uti3 unz-~nl-~nz-r-amime p-~l=v~Nnz (Cl-phenyl))-O-JU2-Ntl2 s i Y 3-am p- z me (Cl-phenyl))-o-JUz-Nriz ~;n3 ~:nz-Lnl-~:nz-~n3-u-amime p-t,l=vyvnz (Cl-phenyl))-O-JU2-Nri2 Ln3 utiz-~nl-~tiz-nn-u-amime p- z (Cl-phenyl))-o-5uz-Ntiz ~ai3 ~ai2 Ltil-t;tiz-rneny-ammo-carooxync m- z (Cl-phenyl))-acid o-JU2-Nti2 1:ri3 1x12-fall-1;ri2-l~1-rrieriyl-ammo m-(Cl-phenyl))-carboxylic acid o-~uz-Nnz ~:n3 ~:nz-~nl-~;nz-r-pnenyi-ammo m-~l=ivnyvnz (Cl-phenyl))-carboxylic acid o-auz-Ntiz ~:n3 ~:nz-~ry-~nz-~;n3 m-~l=mnyvnz pneny-ammo (Cl-phenyl))-carboxylic acid o-~uz Ntiz Lti, ~nz-~nl-~nz-~n3 m-~l=Nn~Nnz u-pnenyi ammo (Cl-phenyl))-carboxylic acid o-~uz-Ntiz ~:n3 ~;nz-~-nlw;nz-tsn-u-pneny m-~l=mnyvnz ammo (Cl-phenyl))-carboxylic acid O-JUZ-Nri2 cai3 ~riz-~nl-~tiz-rneny-ammo m-~l=u~Nnz carnoxync (Cl-phenyl))-acid o-~uz-Ntiz c:n3 ~:nz ~;nl-~nz-~a-pnenyi-ammo m-~l=u~Nnz (Cl-phenyl))-carboxylic acid O-JVy-NriZ c:n3 ~tiz-aril-~nz-r-pnenyi-ammo m- z (Cl-phenyl))-carboxylic acid o- z- 2 3 2 2- 3 m- z P
enY
-~o (Cl-phenyl))-carboxylic acid o-JUZ-Ntl2 cai3 c.;tiz-Lnl-Lnz-Lrl3 m-~;l=uyvnz u-pnenyi-ammo (Cl-phenyl))-carboxylic acid o-~uz-Ntiz s z- z- n- m- z -p eny -ammo (Cl-phenyl))-carboxylic acid o- z- z s z- z- a y p epoxy-aceticm- z (Cl-phenyl))-acid ester o- Z z CH3 CHz-CH~CHZ-Methyl Cl-phenoxyacehcm-(:(=NH)NHz (Cl-phenyl))-acid ester o- z- z CH3 CHz-CH(-CHz-Methyl F-phenoxy-m-C(=NH)NHz acetic (Cl-phenyl))-acid ester o-JU2-NHz ~:H3 ~atz-~:H(-LHz-nnetnym;ti3-pnenoxy-m- z (Cl-phenyl))-acetic acid ester o-5Uz-NHz LH3 t,ttz-~:H(-~;Hz-a Y 3- -P epoxy-m- z (Cl-phenyl))-acetic acid ester O-~Vz-NHz c:H~ MHz-pry-~riz-nnemyi rsn-u-pnenoxym- z (Cl-phenyl))-acetic acid ester CH3 2- z- a y enoxyacehc m- z o- z- 2 (Cl-phenyl))-acid ester o- z- z ~s CHrCH(-CHz-Methyl Cl-phenoxyacehcm-C;(=U)NHz (Cl-phenyl))-acid ester o- z- z - CH3 CHz-CH(-CHz-Methyl r'-phenoxyacehcm- z -(Cl-phenyl))-acid ester o-5U2-NHz C:H3 C;HZ-(:H(-tlHz-a Y 3-p epoxy- m-(Cl-phenyl))-acetic acid ester O-5U2-NHZ 1;H3 C:H2-(:H(-~;Hz-a Y 3- -p epoxy m-(Cl-phenyl))-acetic acid ester o-5Uz-NHz C:H3 caiz-Lti(-LHz-lvlemyl tan-U-pnenoxym-~l=v~wriz (Cl-phenyl))-acetic acid ester o- z- z CH3 CHz CH(-CHz-Yhenoxyacehc m- z acid (Cl-phenyl))-o- Oz-I~HZ CHj CHz-CH(-CHz--p epoxy-acetic m- z aci (Cl-phenyl))-o- z- z CH3 CHz-CH(-CHz-r'-phenoxy- aceticm- z acid (Cl-phenyl))-o- z z CH3 CHz-CH(-CHZCH3-phenoxy-aceticm-C(=NH)NHz acid (Cl-phenyl))-o- z-NHz CH3 CHz-CH(-CHz-CH3-U-phenoxy-aceticm- z (Cl-phenyl))-acid o- z- 2 CH3 CHz-CH(-CHz-n- -p epoxy aceticm- z aci (Cl-phenyl))-o- z- Z ZH3 CHZ CH(-CHz-Phenoxyacehc m- z acid (Cl-phenyl))-o-SOz-NHz CH3 CHz-CH(-CHz-Cl-phenoxyacehc m-c.;(=U)NHz acid (Cl-phenyl))-o-SOz-NHz CH3 z z- -p enoxyacehc m- z aci (Cl-phenyl))-o- z- z ~s z- z- 3-p epoxy-aceticm- z aci (Cl-phenyl))-o- z- z 3 z- z- 3- -p epoxy aceticm- z (Cl-phenyl))-acid o- z- z s CHz CH(-CHz-Bn-U-phenoxy m-C;(=U)NHz acetic acid (Cl-phenyl))-o-SUz-NHz C;H3 I:HZ c:H(-c:Hz-enoxye ano m- z (Cl-phenyl))-o-5uz-NHz c:H3 LHZ ~Hl-~tiz-~i-pnenoxy-emanoim-~l=mnyvriz (Cl-phenyl))-o-SUz-NHz C:H3 LHz-~Hl-c:Hz-r-pnenoxy- emanoim- z (Cl-phenyl))-o-JUZ-NHz C:H3 l:Hz-l;H(-1;H2-1;ri3-pnenoxy-emanoim-~:~=mriJmriz (Cl-phenyl))-O-JVZ-NHZ C:H3 1:H2-l;H(-l:Hz~ri3-u-pnenoxy-emanoim-~~=mryvriz (Cl-phenyl))-O-JUZ-NH2 (a13 1:H2-l:H(-1:ri2-~sn-u-pnenoxy m- z emanoi (Cl-phenyl))-o-~Uz-NHz C:H3 t;tiz-c_:H(-LHZ-enoxye ano m- z (Cl-phenyl))-= 164 -z- z s z- z- Cl-phenoxyethanol m-C(=U)NHz m o-(Cl-phenyl))-o-5Vz-Nriz LH3 LHz-t;Hl-LHz-r-pnenoxy-eulanoi m-~l=u)r~riz (Cl-phenyl))-o-JU2-NHz 1;H3 1:H2-C;H(-C:HZ-LH3-pnenoxy-emanol m-~l=~Jr~riz (Cl-phenyl))-o-~Uz-NHz c:H3 LHz-LHl-LH2LH3-u-pnenoxy- m- z emanol (Cl-phenyl))-o-~UZ Hz ~:H3 c:Hz-~:Hl-~:HZtsn-u-pnenoxy- m-~l=u)lrriz N emanol (Cl-phenyl))-o-JVZ-Nri2 LH3 c:Hz LHl-c:Hz-lviemyl m-~l=r~ri)r~riz pnenoxy-emyl (Cl-phenyl))-ether o-JUz-NHz ~:H, LHz ~;tll-Ltiz-lvlemym;l-pnenoxyetnyl m-~:~=lrri)lvriz (Cl-phenyl))-ether O-JUZ-NHz ~;H, c:Hz tail-Ltiz-1\netnyl m- z r-pnenoxy-emyl (Cl-phenyl))-ether o-~uz-NHz LH3 c:Hz-t_;Hl-MHz-nnetnyl m- z ~ri3-pnenoxy-(Cl-phenyl))-ethyl ether o-~u2 Hz l:Hg C:riz-l;tll-lalz-MeLllyl m-N 1:ri3-V-pnenOXy-(Cl-phenyl))-ethyl ether o-SUz-NHz c:H3 c:Hz-c:Hl-~:Hz-a m- z y n--p enoxy (Cl-phenyl))-ethyl ether o-5Uz-NHz LHj z z- a m- z y enoxye y (Cl-phenyl))-ether o-~Uz-Nriz ~:H, ~;Hz tail-Ltiz-Metnym;i-pnenoxyemyl m-~:~=u)r~riz (Cl-phenyl))-ether o-5Uz-NHz C:H~ (:HZ-t.Hl-(:HZ-a m- z y -p enoxye y (Cl-phenyl))-ether o-JUZ-NHZ 1;H3 l;Hz-l;Hl-l;riz-a m- z Y
a-(Cl-phenyl))- phenoxyethyl ether o-JUZ-NHz 1;H3 1;H2-l;Hl-C;tiz-i vletnyl Sri,-u-m-(Cl-phenyl))- phenoxyethyl ether o-~Vz-NHz uH, c:Hz-uHl-c:HZ- Memyl tsn-u- m-~l=u)wriz (Cl-phenyl))-phenoxyethyl ether O-JU2-Nriz c:H3 LHz-~Hl-MHz-phenyl m-~l=r~ri)r~tiz ~z)-O-JUz-NHz 1;H3 (:HZ-l;Hl-C;HZ-l:l-prienyl m- z ~z)-o-~uz HZ 1:H3 1:H2-l;Hl-l;Hz-r-prieriyl m-l:l=1Vri)1Vr12 N
~z)-O-~UZ-NHZ C:Hj (.;H~ t.Hl-LrlZ-j-p m-eny ~z)-O-JUZ-NHZ C:Hj l:Hz l;Hl-lain-3- m- z -p eny NHz)_ O-JVZ-NHz C;H3 l:Hz-l;Hl-1;H2-tfn-U-phenyl m-NHz)-O-JUZ-lVtiz 3 2- r P m- z enY
~z)-o-z- z s r r -p m- =O)NHz eny ~z)-z- 2 3 2 2' -p m- z eny ~2)-O-5Uy-NH2 1;H3 l:H2l:Hl-1;H2-3-p m-eriy NHz)_ o-5u2 Hz s z- z- 3- m- z N -p eny ~z)-o-Oz-NHz CH3 z- z- n- m- z -p eny NHz)-O-JUZ-NHZ 1;H3 l:Hz-l:Hl-l;Hz-11I1e p-~2)-O-JUz t12 1;ri3 l;rii l;tll-~riz_-am p- z 1V me ~2)-o-z- 2 3 2- z- -am p-me ~z)-O-SUz-NHZ lal3 l;Hz-l:H(-l:Hz-3-ant p-me ~z)-o-SUz-NHz s z- r 3- p- z -am me NHz)_ o-5U2-NHZ C:H3 1;H2-C;H(-C:HZ-n_ p--am me ~z)_ o-z- z s z- z- i p-C(=O)NHZ
me ~z)-o-z- z s z- z- -atli p-C(=O)N
me ~z)-o-5Uz-NH2 1;H3 C:HZ-l;H(-l:Hz -ant p-me ~z)-o-5Uz-NHz C:H3 C:Hz-1:H(-I~HZ 3-am p- z me NHz)_ 2- 2 3 2- 2- 3- p-l.(=V)1Vr12 -~1 me NHz)_ o-5UZ-NHZ C:H3 l;Hz l:Hz-tSn-u-arillme p-l;ti(-~z)-o-~uz-NHz cal3 c:Hz-t_;H(-l:Hz-eny m- z -ammo-car oxy is NHz)- acid o-5V2 HZ 1;H3 lalz-lal(-1x12-l;l-Ynenyl-ammo m-N
NHz)- carboxylic acid O-5UZ-NHZ 1x13 1;H2-l:H(-l;Hz-r-pnenyl-ammo m-NHz)- carboxylic acid o-~uz Hz 1x13 l;Hz-1:H(-l:Hz-1x13-pnenyi-ammo m- z N
NHz)- carboxylic acid o-~Uz Hz 1:H3 c:Hz lalz-3_ m- z N 1:H(- _p eny ammo NHz)- carboxylic acid o-JUZ-NHZ 1;H3 C;tl2-C:H(-t;H2-n- m- z -p eny ammo NHz)- carboxylic acid o-5V2-NH2 1x13 1:H2-l:H(-l;tlZ-Yrienyl-ammo m-CarDOXyIIC
NHz)- acid o-5uZ-NHZ 1x13 1:H2-l;H(-l:rlz_-p y -ammo m- z en NHz)- carboxylic acid o-5uz-NHz 1x13 l:Hz l;tlz-r-pnenyi-ammo m- z 1:H(-NHz)- carboxylic acid O-JUz-NHZ 1:H3 l;tlz 1;H2-1;H3-prieriyl-ammo m-l:(=U)1Vr12 ljH(-NHz)- carboxylic acid o-JUZ-NHZ l;ti3 l.:Hz-l;H(-1:H2-1x13-u-prienyl-ammo m-l.;(=V)1Vr12 NHz)- carboxylic acid o-~uz-NHz 1x13 lalz-lal(-l;tlz-tsn-u-pnenyi-ammo m- z NHz)- carboxylic acid o--SO~lHz CH3 CHz-CH(-CHz- Methyl m-C(=NH)NHz phenoxy-acetic NHz)- acid ester ~ OZ Hz CH3 CHz-CH(-CHz- Methyl m- z N Cl-phenoxyacehc NHz)- acid ester o-r z-- s CHz-CH(-CHz- Methyl m- z r'-phenoxy-acetic NHz)- acid ester o-5uz-NHz 1:H3 1:H~ l:Hz-ivlemyi m-1:(=~ri)wriz 1;H(- l:rl3-pnenoxy-NHz)- acetic acid ester O-JUZ-Nri2 l:Hg (:Hz-lal(-l:riZ-a m-Y
s' -P
enOXy-NHz)- acetic acid ester o-~uz-NHz 1:H3 z- z- a m- z y n--p enoxy NHz)- acetic acid ester z- z s z- z- a Y ,_,~ ~.,,...
enoxyacehc m-NHz)- acid ester o-z- z s z- z- a m- z Y
-p enoxyacehc NHz)- acid ester c-r z s z- z- a m- )NHz y -p enoxyacehc NHz)- acid ester o-2 2 3 2- z- a Y s-P epoxy- m-t_:~=~~~riz NHz)- acetic acid ester o-z- 2 3 2- z- m~(=O)NHz 11 u1 m.aa v a Y 3 -P epoxy NHz)- acetic acid ester o'z- 2 3 2- r a y n- -p epoxy m- (-O)~z NHz)- acetic acid ester o-z- z s z- z- enoxyacehc aci m- (=~H2 NHz)_ -o-z- 2 3 2- z- -p epoxy-acetic m- (=NHjl~Hz aci ~z)-o-z- z s r z- -P epoxy- aceticm- z aci ~z)-o-r z s z- z- ,-p epoxy-aceticm- z aci ~z)-o-z- z z- z- ,- -p epoxy-aceticm- z ~,~1 s NHz)- acid - -o-z- z s z- z- n~(=RH)NHz n- -p epoxy acetic acmT
~z) o-z- z a r z- enoxyacehc aci m- 2 ~2)-o-z- z 3 CHz CHz- -p enoxyacehc m- z CH(- aci ~z)-o-z- z CH3 CHz-CH(-CHz- r~-phenoxyacehc m- z acid NHz)_ o-z- z 3 CHZ CHz- CH3 phenoxy-aceticm- z CH(- acid NHz)_ o-z z CH3 CHz-CH(-CHz- CH3-U-phenoxy m- z acetic NHz)- acid o-z- z CH3 CHz-CH(-CHz 13n-U-phenoxy m- z acetic acid ~2)-o-5Uz-NHz CH3 t;Hz-c:Hl-LHz- rnenoxyemanoi m- z NHz)_ o-5Uz-NHz C;H3 LHz Lttz--p epoxy-a ano m- z LHl-~z)_ o-z- z s z z- -p epoxy- a ano m- z ~z)-o-5Uz-NHz C:H3 ~ r 3 p epoxy-a ano m- z ~z)-o-SUz-NHz C:H3 i z- 3- -p epoxy-a m- z ano ~z)-o-r z 3 z- z- n- -p epoxy a m- (=NH)NHz ano ~z)-o-SUz-NHz C:H3 z- z- enoxye ano m- z ~z)-o-z- z 3 z- z- -p enoxye ano m- =O)NHz NHz)_ o-5Uz-NHz C:H3 (:Hz LHz- r-pnenoxy-emanoim- z t_;Hl-NHz)_ o-z- z 3 z- z- 3-p epoxy-a ano m- z ~z)-o-JUZ Hz C:H3 c:Hz-fail-~:Hz-Lti3-u-pnenoxy- m- z N emanoi ~z)-o-5uz-NHZ LH3 e:Hz-LHl-MHz- tin-u-pnenoxy- m- z emanoi ~z)-o-z- z s r r a y p epoxy-a m- z y NHz)- ether o-z- z s z- z- a y -p enoxye m-y NHz)- ether o-z- z s z- z- a y -p epoxy-a m- z y NHz)- ether o-z- z 3 z- z ' P epoxy- m- NHZ
~
e ~ e z) ther Y
0-JVZ-NHz s z- z- et m-y -p enoxy-NHz)- ethyl - ether o-SOz-NHz CH3 CIA- z- a m- z Vlll -vlly n--p enoxy NHz)- ethyl - ether o-Saz-~ CH3 a m- z ull -ully vll~ z- enoxye z- y NHz)- ether o-SOz-NHz ~3 - z- z_ a m- z - y _p enoxye y NHz)- ether o-SOz-Nx2 C1~ - a m- z fill -vllY
Vlll r -p z- enoxye y NHz)- ether o-JVZ-lVriz 1;H3 1.;H2-l:H(-C:H2-Nlettlyl m-(.:(~)NH2 C;Hj-NHz)- phenoxyethyl ether O-JV2-1Vt12 1.;H3 (:HZ-l:H(-laiZ- Methyl C;H3-U- m-(:(~)NHz NHz)- phenoxyethyl ether o- wz-NHZ ~H3 ~Hz-~Hl-~Hz- Methyl tin-V- m-C(=V)NHz NHz)- phenoxyethyl ether Other preferred compounds of formula I, having the sub-formula Ib, are set forth in Table 76, below.
Table 76 Formula III
L
s R
o- z- z enyl m_y ~~z _ o- z- z z _p m-eny o_ z- z - -p m_C(-~~z enyl-z- 2 2 3- P m- z enY
o' z- z z 3- ~ p end Iri-~z o- z- z z n_ p m- z _ eny o- z- z 2 ehyl m-C~~)~z o- z- z z -p m_C~-0)~z eny o- z- z z -p m_ eny o' z- z z ,- p m=i -eny o- z- z z ~- - p eny m_ o z n_ eny m Z
z- z - _p o- z- z z i p-~:(=mtt~r~riz me o- z- z z a P- z o- z- z z -am P~~z the o- z- z z 3-am p- z the o- z- z z 3- P- z -~
a o- z- z z n- p-t,(=~tt~~tiz me o- z- z z a P' z o- z- z z me P- z o- z- z z -am p_ z me o- z- z z 3-am p_ z me o- z- z z ~- p_ z -am a o- z- z z n_ p-_a me z- z z eny m- z -ammo-car oxy c acid o- z- z z eny m- z -amino car oxy is aci o- z- z z -p m- z eny -ammo carboxylic acid o-~uz-wtiz r~ l,riz l:ri3-pnenyi-ammo m-t,(=Nti)Nriz carboxylic acid O-JVZ-Ntiz t~ laiz l:ri3-u-pnenyi m-1:(=Nti)Nriz ammo carboxylic acid o-~uz-Ntiz r~ l:riz rsn-u-pnenyi m- z ammo carboxylic acid o-JUZ-NtlZ ri Z eriy m--ammo car OXy 1c acid O-JVZ-NHZ H z -p m- z eny -ammo carboxylic acid O-~Uz-NHz ti talz r-phenyl-ammo m- z carboxylic acid o-~Uz-NHz W a1z ~ai3-phenyl-ammo m- z carboxylic acid o-JUz-NHZ H 1x12 lai3-u-pnenyi-ammo m-~(=u)rVriz carboxylic acid o-JUZ NHz ti laiz tsn-u-phenyl-ammo m-1J(=U)ivrtz carboxylic acid o-SU~lHz H C;Hz Methyl m-C;(=NH)NHz phenoxy-acehc acid ester o- Oz-NHz H (:Hz Methyl m-C;(=NH)NHz (:1-phenoxyacehc acid ester o- z- z - H CHz Methyl m- z - r'-phenoxy-acehc acid ester O-SUZ-NHZ H laiz Metnyi m- z l:ri3-pnenoxy-acetic acid ester o-SUZ-NHZ H 1:H2 MeTllyllal3-u-prieriOXy- m- y acetic acid ester o-SUz-NHz H LHz Merry m- z tsn-u-pnenoxy acetic acid ester o- Z z H - CHz Methyl m- z - Yhenoxyacehc .
acid ester o- z- z z - Methyl m-C;(=U)NHz C1-phenoxyacehc acid ester o- z- z 2- Methyl m- z F-phenoxyacehc acid ester o-SUz-NHz H c:Hz a m- z y 3-p epoxy-acetic acid ester O-SUZ-NHZ H c:Hz Memyi m- z l:rij-u-pnenoxy acetic acid ester o-SUZ-Nri2 H c:riz enemy m-1:(=u)mriz tsn-u-pnenoxy acetic acid ester o- z- z z enoxyacehc m- z aci o- z- z z -p m-epoxy-acehc aci o- r z z -p m-C;(=NH)NHz epoxy-acehc aci o- r z z 3- p epoxy-acehcm- z aci o- z- z z 3- m- z -p epoxy-acehc acid o- z- z z n- m- z -p -epoxy acehc aci o- r z z enoxyacehc m- NHz aci o- z- z z -p m-enoxyacehc aci o- r z z -p m-enoxyacehc -aci o- r z z 3-p m- NHz epoxy-acehc -aci o- z- z z 3- m- 2 -p epoxy acehc acid o- z- z z n- m- z -p epoxy acehc aci o- z- z z enoxye m- )NHz ano o- r z z -p m-epoxy-a ano o-2 z H z -p m-- epoxy=
ethanol -o-z- z H z 3-p m- z - epoxy-a ano o-z- z H z 3- p epoxy-etTianolm- z - -o-z- z H z n- epoxy a m- z - ---p ano o~z-~HZ H Cf ~ enoxyethanol m o-z- z H z -p m- z - - enoxyetfiano o-z- z H CIA F=pfienox~ol iris o-z- z z 3- p m- z . _ epoxy-a ano o-- ~2 ~3=a=p~enoXy-ethapolm-C'~
-o-- z ~ n_ epoxy- ethanolmZ'(=O)NF~
_p o-z- z z ethy m-C(=
p epoxy-et y ether o-~uz-Nriz ti ~riz nnemyi m-~(=Nri)Nriz m-pnenoxyemyi ether o-~uz-Ntiz z a m- z y -p epoxy-a y ether O-JUz-Nriz trtiz a m- z y 3-p epoxy-ethyl ether O-JUz-Ntiz ti trtiz. nnemym:ri3-u-pnenoxy- m- z ethyl ether O-JVz-Nriz m aiz nnemyi m- z tsn-u-pnenoxy ethyl ether o-JUz-Ntlz n l.;tlz MeTtlyl m- z YnenOXyelllyl ether O-~Uz-Nriz t m ;tiz Mewyma-pnenoxyemyi m-~,(=u)mnz ether o-5Vz-Nriz ti Ltiz Memyi m-~(=u)~riz r-pnenoxyemyi ether o-5Uz-NHz rt ~:riz nnetnymai3- m-~:(=u)Nriz phenoxyethyl ether o-JUz-Ntlz ti uriz memyi m-~,(=v)mriz ~ri3-u-phenoxyethylether o-JVz-Ntlz H lalz Melllyl m-L(=U)lVtlz tSn-U-phenoxyethyl ether o-z- z z- z P m- z enY
o-z- z z- z -P m-~-(=Nti)Ntiz enY
o-z z z- z -P m- z enY
z- z z- z a- P m- z enY
n-r z z- z 3- - p eny in~(=NH)NHz o-r z z- z n_ eny m- z _p o-z- z r z P m- )~z enY
o-z- z z- z -P m-~;(=u)mriz enY
o-r z z- z -P m- z enY
o-r z r z s- P m- z enY
o-z- z z- z ,- - p eny m- z o-z- z z- z n_ eny m- _ ~NHz _p o-z- z z- z m p- z me o-z- z z- z -am p- z me o-z- z z- z -am p- z me o-z- z z- z 3-am p-me z z z- z 3- p- z -am me o-z- z z- z n_ p-_~
me o-z- z z z m p- z me o-z- z z- z -am p- z me o-r z z- z -ani p- z ' me o-z- z z- z 3-am p- z me o-r z r z 3- p_ z -am -me o-z- z z- z n_ p- z _~
me o-r z z- z eny m- z -ammo-car oxy is acid o-z z z- z enY m- )~z -o car oxy is aci O-~Uz-NHz z- z -p m- z eny -ammo carboxylic acid O-lVZ-Ntiz h l;rlz-l:HZ uri3-pnenyi-ammo m-~:(=r~riJr~riz carboxylic acid O-JUz-NHz ri uriz-uriz ~ai3-u-pnenyi m-~:(=r~tiJNtiz ammo carboxylic acid o-~uz-Ntiz m ;tiz-~riz rsn-u-pnenyi m-~(=ivriJNriz ammo carboxylic acid o-~uz-Ntiz n uriz-~riz rnenyi-ammo m-~(=uJwriz carnoxync acid O-~uz-Ntiz ri uriz-~riz m-pnen yi-ammo m-~(=uJwriz carboxyl ic acid o-~uz-Nriz ri ~riz-~riz r-pnenyi-ammo m-~(=uJrrriz carboxylic acid o-~uz-Ntiz tm -rIZ-~-riz ~:r13-pnenyi-ammo m- z carboxylic acid o-~uz-Ntiz tm ;riz-taiz ~;ry-u-pnenyi-ammo m- z carboxylic acid O-aVz-NHz H l;riz-lalz tSn-V-prienyl-ammo m-carboxylic acid o- z- z - H z- z a m- z y p epoxy-acehc acid ester o- z- z z- z a m- z y -p enoxyacehc acid ester o- z- z z- z a m- z y -p epoxy-acehc acid ester o-5Uz-NHz H Ltlz-~ttz lviemyi m- z ~ri3 pnenoxy-acetic acid ester o-~Uz-NHz H C:Hz-l:Hz Metnyl m-t_;t13-u-pnenoxy-acetic acid ester o-5Uz-NHz H c:Hz-LHz Memyi m- z rsn-u-pnenoxy acetic acid ester o- z z CHz CHz Methyl m- z Yhenoxyacehc acid ester o- z- z H CHz CHz Methyl m- z C1-phenoxyacehc acid ester o- z- 2 H CHz-CHz Methyl m- z r'-phenoxyacehc acid ester o-SVz-Nri2 H ~:Hz-LHz Memym;tl3 m- z pnenoxy-acetic acid ester o-5Uz-NHz H c:H2 LHz Memyi m-~(=uJwriz Lti3-u-pnenoxy acetic acid ester O-5U2-NHz H 1;H2-(:Hz lVlelllyl m- z tiri-V-prierioxy acetic acid ester o- z- z z- z enoxyacehc m- z aci -o- z- z z- z -p m- 2 epoxy-acehc aci o- z- z z- z -p m-(:(=NH)NHz epoxy-acehc aci o- z- z z- z 3-p m- z epoxy-acehc aci o- 2 2 2 2 3- m- z -p epoxy-acehc acid o- z- z z- z n- m- z -p epoxy acehc aci o- z- z z- z enoxyacehc m ~~~)NHz aci o- z- z z- z -p m- z enoxyacehc aci o- z- z z- z -p m- z enoxyacehc aci o- z- z z z 3- p ri-C(=O)NHz epoxy-acehc acm o-S02-NHz H CHz-CHz CH3-U-phenoxy m- z acehc acid o- z- z z- z n- m- z -p epoxy acehc aci o- z- z z- z enoxye m- =NH)NHz o o- z- z z- z -p m- NHz epoxy-a ano o-z- z z- z -p m- z epoxy-ethano o-z- z r z 3_ p m- z epoxy=et ano o-z- z z- z LHa- u_pnenoxy-emanolm- rlz o-z- z z- z n- epoxy a m- z -p ano o-z- z z- z enoxyethano~ m o-z- z r z -p m- z enoxye -ano o-z- z z- z -p m-C(=O)NITz epoxy-ethanol o-z- z z- z ,-p m-C(=
epoxy-e~
o-z- z z- z 3- p epoxy- m- z - a ano -o-z- z z- z n- enoXy- e~ rim-C(=O) -p --o-z- z z- z a m-C(=NH)I~lFi2 yTp epoxy-et y ether o-~uz-lvrlz m ;riz-~riz lvleulyl m- z m-pnenoxyemyl ether O-JUZ-NriZ ti ~tiz-~tiz lvlemyl m-~l=lvrl)lvrlz r-pnenoxy-emyl ether O-JUz-lvtlz ri ~:rizriz enemy m-~~=lvrl)lvrlz ~ ~ri3-pnenoxy-ethyl ether o-~uz-Ntiz t m ;tiz-~riz enemy m- z ~ri3 u-pnenoxy-ethyl ether o-~uz-lvtlz ti ~riz-~riz lvlewyl m-~~=lvrl)lvrlz rsn-u-pnenoxy ethyl ether o-~Uz-Ntiz ti ~aiz-~aiz lvlemyl m-~:(=v)lvrlz rnenoxyemyl ether o-~uz-lvtiz t1 Ltlz-~aiz nnetnym;i-pnenoxyemyl m-t.~=v)lvrlz ether o-5uz-lvtiz t1 Ltlz-Ltlz lvlemyl m- z r-pnenoxyemyl ether o-JUZ-lVri2 H i z a m- z Y
phenoxyethylether O-JU2-NtiZ ti ~riz-~riz lvlemyl m- z Sri,-u-phenoxyethylether o-SUz-Nriz ti calz-Ltlz l vleulyl m-~~=U)lvrlz tsn-u-phenoxyethylether o-z- z r r z P m- z eriY
o-z- z z z-z -p m- z enY
o-z- z r r z -p m- ~z enY
o-r z z- z z a- p m- z enY
o-z- z z- z-2 3_ - p eny m-~:~=lvrl)lvrlz o-z- z z- z-Z ri_ eny m-_p o-z z r z-z p m=C(=~~z eny o-z- z z- z-z -p m- z enY
o-r z z- z-z _p m-eny o-z- z z- z-z 3 p m- ~z eriY
o-z- z z r z 3- _ p eny m_ (~z o-z- z z- z-z n_ eny m- z _p z- z r z-z lee p_ -o-z- z z- z-z -am p- z me o-z- z z_ z_z -am p- z me o-z- z z- z-z 3-am p- (=z me o-z- z z- z-z 3 p- z -am me o-z- z r r z n_ p- ~NIT)NHz _~llne o-r z r z'z m p- z lee o-z- z z- z-z -am p- z me o-z- z z- z-z -aril p_ 2 me o-i z r z-z 3-am p- ~ O)NHZ
me o-z- z z- z-z 3- p- z -and me o-z- z z- r z n_ p_ 2 _am me o-z- z z- z-z eny m- NFfz -amino-car oxy lc acid o-z- z z- z z eny m- z -alnlno car oxy is aci o-SOz-NHz H CHz-CHz-CH2 -p m enyl-amino carboxylic acid o-~u2 riz m :riz-~:riz-t,riz ~ri3-pnenyi-ammo m-~:~=NtyNtiz m carboxylic acid o-~u2 riz m ;riz-~:riz-t,tiz ~ri3-u-pnenyi m-t.~=NtyNtiz m ammo carboxylic acid o-~u2 riz n ~riz-~rizriz nn-u-pnenyi m-~~=NryNriz N ~ ammo carboxylic acid O-JUZ-Nriz z- r z eny m- z -ammo car oxy is acid o-z- z r z-z -p m- z eny -ammo carboxylic acid O-JU2-Nriz z- r z -p m- z eny -ammo carboxylic acid O-JVz tiz tm ;tiz-~:riz-~:riz ~ai3-pnenyi-ammo m- z N carboxylic acid o-JUz tiz H ~alz-Lttz-~alz 3- m- z N -p eny -ammo carboxylic acid O-JU2 HZ ti lalz ri2-l:riy tSn-u-pnenYi-amino m-N 1; carboxylic acid o-SOz~Hz H CHz-CHz-CHz Methyl m-C(=NH)NHz phenoxy-acetic acid ester o-SOz-NHz H CHz-CHz-CHz Methyl m-C:(=NH)NHz C:1-phenoxyacehc acid ester o-SOz-NHz H CHz-CHz-CHz Methyl m-(:(=NH)NHz >~~-phenoxy-acetic acid ester o-~u2 Hz H l;tiz-~atz-~alz lvletnym;tlj-pnenoxy- m-~:(=r~ri)rVriz N acetic acid ester O-JVZ-NHZ ti 1:H2-1;H2-1;H2 lVlelllYi m-l:~=lVt1)Ntlz l;tlg-u-pnenOXY-acetic acid ester o-~uz-NHz H ~tiz-~riz-~-tiz iviemyi m- z nn-u-pnenoxy acetic acid ester o-SOz-NHz H CHz HzHz Methyl m- z C C Yhenoxyacetic acid ester o-SOz-NHz H i Z z a m- z y -p enoxyacehc acid ester o-z- z - ~I CHz HZHz Methyl m- z C C F-phenoxyacetic acid ester o-~u2-NHz H ~aiz-~ay-cay a m- z y 3-p epoxy-acetic acid ester O-JUZ-NHz H Ltlz-LHz-c:Hz iviemyi m- z ~ri3-u-pnenoxy acetic acid ester o-JUZ-NHZ H C;H2-l:riz-1:ri2 lVlelllYi m-tSn-u-prieriOXY
acetic acid ester o-z- z z- z-z enoxyacehc m- z . aci o-z- z z- z-z -p iri-C(=NIT)NHz epoxy-acetic aci o-z z z r z -p m- z epoxy-acetic aci o-z- z z- z-z 3-p m-epoxy-acetic aci o-r z r r z s- m-C(=NH)NHz -p epoxy-acetic acid .
o-r z r z-z n- m- z -p epoxy acetic aci o-z z z- z-z enoxyacehc m-aci o-r z r z-z -p m- z enoxyacehc aci o-z- z r z-z -p m-(:(=U)NHz enoxyacehc aci o-z- z z- z-z 3- p epoxy-aceticm- z aci o-z- z z- z-z a- m--p epoxy acetic acid o-z- z z- z-z n- m- z -p epoxy acetic aci o-z- z z- z-z ~ m- NH NHz enoxye ano o-z- z z- z-z -p m- z epoxy-a ano o-r z z- z-z -p m- z - epoxy-a ano o-z- z g r z-z 3-p m- z epoxy-ethanol o-z z r r z 3- p epoxy-a m- z - ano o-z- z ~ z- z-z n- epoxy ethanem--p -o-z- z z- z-z enoxye m- z ano -o-z- z z- z-z -p m-enoxye anoI
_ o-z- z ~z- ~z-~z -phenoxy-ethanol m~O)IVHz o-z- z z- z-z 3- p m- z epoxy-a ano o-z- z ~C HZ=z 3- O-p~enox~anolm- z o-z- z CH2= z-z n- epoxy- ethanolm- (= z -p o-z- z z- z-z a m- z y p epoxy-a y ether o-~uz-wriz ti ~riz riz-~rizmemym;i-pnenoxyeuryi m-~.I=mryvriz ~;
ether O-JUz-lVri2 ti z- z-z a m- z y -p epoxy-a y ether o-SOz-NHz H CHz Hz-(:Hz ' m- z C; a y 3-p epoxy-ethyl ether O-5u2-NHZ ti z- z-z a m- z y -p epoxy-ethyl ether O-JUz-Nriz t-~ ~tiz-c:riz-~tizMemyi m- z rsn-u-pnenoxy ethyl ether O-JUZ-NHZ ri Ltiz-cai2rizMemyi m- z ~ rnenoxyemyi ether o-SOz-NHz H CHz-CHz-CHz et m- z y -p enoxye y ether o-~uz-Ntiz ti ~riz-~nz-~nz memYl m- z r-pnenoxyemyi ether O-JU2-Nri2 H caiz-~tiz-~tizMetnyi m-~I=u~wriz ~ri3-phenoxyethyl ether o-~uz-Ntiz t-~ ~tiz-~riz-~rizMemyi m-~l=uyvriz ~ri3-u-phenoxyethyl ether O-JUZ-1VH2 ti ~tiz-~riz-Ltizenemy m-~~=u~wriz ~n-u-phenoxyethylether o-z- z z- s P m- z - enY
o-z- z z- 3 -p m_ - eny o-z- z z- 3 -p m-~.~=mtiyvtiz - eny ~
o-r z z- s 3- P m- z - enY
-o-r z z- 3 3- - p enyI m-C(=NH)NHz -o-z- z z- 3 n- eny m- z - -p o-z- z z- 3 P m-_ enY
o-~u2 tiz z- , -p m-~t=u~wriz N - eny o-z- z z- 3 -p m-~~=uyvriz - eny o-z- z z- 3 a-P m-~-l=u)ivtiz - enY
o-z- z z 3 s- P eny m- (=O)NHz - - -o-z- z z- s n- enyl m-C(=O)NHz - -p o-r z z- j m p- z - me o-z- z z- 3 -am p- ~z - me o-z- z z- 3 -am p_ - me o-z- z z- s 3-am P_ z - me o-z- z z- s 3- p- NHZ
- -am me -o-z- z z- s n- P-C(-~)~z - -am ine o-z- z z- 3 me P_ z -o-z- z z- 3 -am p-- me o-z- z z- 3 -am p-~t=ulwriz - me o-z- z z- s 3 p-~t=u~wriz - am me o-z- z r s 3- p- =O)NHz - -aniline o-z- z r 3 n- p-~~=uyvriz - -am me o-z- z z- 3 eny ~(=NH)NHz - -amino-car oxy is acid o-r z z- s eny m- z - -ammo car oxy is acid o- r z r 3 _ -p m- z .. eny -ammo carboxylic acid o- - z H CHz_ 3 - 3_p m-w ma v.u~-w.u eny ~ -amino w m a carboxylic acid O-JVZ-Nriz ri ~riz-Sri(-~ri3)-~:ri3-v-pneny m-~~=wri)~tiz ammo carboxylic acid O-JUz-Nriz ri ~riz-~ri~-~ri3)-nn-u-pnenyi m-~~=~ri)Nriz ammo carboxylic acid o-JVZ-Nriz ri 1;ri2-l;ri(-l:rig)-Ynenyl-ammo m-l:(=V)lVriz CarDOXyIIC
acid o-~uz-Nriz n z- 3 - m-pnenyi-ammo m- z carboxylic acid O-JVZ-iVriz ri l:riz l;tl(-1;t13)-r-pnenyi-ammo m-~~=u)r~riz carboxylic acid o- z- z z- s - s-P m- z enY
-o carboxylic acid O-JVz-wtiz ri ~:riz-t,ri~-~ri3)-~:ri3-u-pnenyi-ammo m-~;~=~Jivriz carboxylic acid O-JVz-Ntiz ti ~riz-Sri(-~ri3)-tsn-u-pnenyi-ammo m-~~=u)~riz carboxylic acid o- z- z CHz-CH(-CH3)-Methyl m-C(=NH)NHz phenoxy-acetic acid ester o-SOZ-NHz H z- , - a m- z y -p enoxyacehc acid ester --o- z- z z- a - acetic iri-C(=NH)NHz ma ua a a-as a y -p epoxy=
acid ester o- z- z z- s - m-C(=NH)NHz avi ua a a.,.aJ, as a y p epoxy-acetic acid ester o- z- z z- s - m- )NHz m v~ a, ua a a..a.a, v a a Y
s--p epoxy-acetic acid ester o- z- z z- s - a m- )NHz Y ,.~ a,~~
n--p epoxy acetic acid ester o- z- z z- s - a m-C(=O)NHz y enoxyaceric acid ester o- z- z H CHz-CH(-CH3)-Methyl m-C(=U)NHz Cl-phenoxyacehc acid ester o-S~-NHz H CHz-CH(-CH3)-Methyl m- z F-phenoxyacehc acid ester o-JVi NHZ ti 1:ri2-l:tl(-Cal3)-Melllyl m-l;(=u)lVriz 1;ri3-prienOXy-acetic acid ester o-5u2 Ntiz tm :riz-pry-~ri3)-nnemyi m-~~=u)~riz ~ri3-u-pnenoxy acetic acid ester o- r z z- 3 - a m- z y n--p epoxy acetic acid ester o- r z r 3 - enoxyacetic m- z aci o- z- z r s - -p m-C(=NH)NHz epoxy-acetic aci o- z- z z- s - -p m-epoxy-acetic aci o- z- z z- s - 3- p epoxy-aceticm- NHz aci o- z- z z- s - 3- m-C(=NH)NHz -p enoXy=acettc acid o- z- z z- s - n- m- z -p epoxy acetic aci o- z- z z- s - enoxyacehc m- z aci o- z- z z- 3 - -p m- z enoxyacehc aci o- z- z ? 3 - -p m- (=O)NHz enoxyacehc aci o- z- z z- s - ,-p m- NHz epoxy-aceric aci o- z- z z- s - s--p y vy,i epoxy m-acetic acid o- z- z z- 3 - n- m--p epoxy acetic aci o- z- z z 3 - enoxyetIiano m=C(=NH)NHz o- z- z z- s - -p m-epoxy-a ano o-z- z r 3 -p m- 2 - epoxy-a ano o-z- z z- 3 3-p m-~:~=~ti)mriz - epoxy-a ano o-z- z z- , ,- p erioxy-a in~NHz - - anol o-z- z z- s n- epoxy ethanom- z - -p o-z- z z- 3 enoxye m-~:~=u)rrttz - ano o-z- z z- 3 -p m-~:~=~)Nriz - enoxye ano o-z- z r 3 -p m-- epoxy-a ano -o-z- z z- 3 ; P m- )~2 - epoxy-a ano o-z- z z- s 3- - p epoxy- m-C
- a ano o-z- z z- 3 n- epoxy- a m-C(=O~NHz - -p anol o-z- z z 3 a m_ - y w.~ awa~a.aa p epoxy-a y ether o-z- z z- 3 a m~z - Y
-p enoxye yl-ether o-~uz-Ntiz m aiz-pry-~rij)-a m- z y -p epoxy-a y ether O-JU2-Ntlz ti ~tiz-~ti(-~ri3)-enemy m- z Sri,-pnenoxy-ethyl ether O-JUZ-Nriz t m aiz -~ri3)-Memyi m-~~=rrri)r~riz cay ~n3-u-pnenoxy-ethyl ether O-JUz-Nriz t m aiz-pat(-~ai3)-nnemyi m-~~=~ri)~riz nn-u-pnenoxy ethyl ether o-~uz-lvttz t m aiz -cai3)-nnemyi m-~~=u)~riz gay rnenoxyemyi ether o-z z z- s a m- z - y -p enoxye y ether o-z- z z- s a m- =O)NHz - y -p enoxye y ether 3 x m-C =O NH
( ) 2 yethyl ether phen 3 x m O NH
z yethyl ether phen o-z- z z- 3 o m-C(=O)NHz .
phen yethyl ether o-z z z_ z p m-C(=~)NHz _ eny o_z_ , z_ z -p m_ _ eny o-z- z z z -p m- z - eny o-z- z z- z s-P m- z - enY
o-z- z z- z 3- p eny m- z - -o-z- z z- z n- enY . tn-C( NH)NHz - -P
o-z- z z- z P m- z - enY
o-z- z z- z -p m-- eny o-z z z z -p m-- eny o-z- z z- z s- P m- ~ O~z - enY
o-z- z z- z 3- - p eny m- =O)~z -o-z- z z- z n- eny m- z - -p o-z- z z- z me p-t.;(=rrti)rVtiz -o-z- z z- z -am p-C(=NH)NHz - me o-z- z z- z -am p- z - me o-z- z z- z 3-am p-C(=NH)NHz - me 2- 2 2 2 3- p-l,~=iVt1)1Vt12 - -anl llle o-z- z z- z n- p-C(=NH)NHz - -am me o-z- z z z m p-l.;(=u)mtlz - me o-z- z z- z -am p- )NHz - me o-z- z z- z -am p- z - me o-z- z z- z 3 p-~;(=u)rVriz - am -me o-z- z r z 3- p- z - -am me o-z- z r z n- p- z - -am me o-z- z z- z eny m-~~=~ri)mriz - -ammo-car oxy is acid o-z- z z- z eny m- )NHz - -ammo car oxy tc act o-~uz-NHz ri ~riz-pry-r~riz~-r-pnenyt-ammo m-~~=lrryrrriz carboxylic acid O-JVz-lVriz ri ~riz-Sri(-r~riz)-~ri3-pnenyt-ammo m-~t=ruryrrriz carboxylic acid O-JUz-lVriz ri ~riz-Sri(-r~riz)-~ri3-u-pnenyt m-~~=t~riJlrriz ammo carboxylic acid O-JUz-NHz ri ~;riz Sri(-Nriz)-tsn-u-pnenyt m-~:~=rrtyNtiz ammo carboxylic acid O-JV2 NHz i z - eny m- z -ammo car oxy tc acid o- z- z z- z - -p m- --U) eny z -ammo ,.~ ~,..
carboxylic acid o- z- z r z - -p m-C(=O)NHz eny -ammo .-..
carboxylic acid o- z- z CHz-CH~NH~-CH3-phenyl-amino m-C(=U)NHz carboxylic acid O-JVz-NHZ ri ~riz-Sri(-rVriz)-~:rt3-u-pnenyt-ammo m- z carboxylic acid O-JUy-NHZ H MHz-qty-lrriz~-rsn-u-pnenyt-ammo m-~t=u~rrriz carboxylic acid o-SOz-NHz H CHz-CH(-NHz)-Methyl m- z phenoxy-acetic acid ester o- z- z H CHz CH(-NHz)-Methyl m- z C1-phenoxyacehc acid ester o- r z z- z - a m- =NH)NHz y -p epoxy-acetic acid ester o- z- z z- z - a m-C(=NH)NHz y 3-p epoxy-ivi ua a m as acetic acid ester o- z- z z- z - a m=C(=
Y
-p epoxy-acetic acid ester o- z- z z- z - m_C(-z iva m a a v a a Y
n--p epoxy acetic acid ester o- r z z- z - m-C(=O)NHz u1 L
a y enoxyacetic acid ester o- z- z z- z - a m- =O)NHz Y
-p enoxyacehc acid ester o- z- z z- z - a m- =O)NHz Y
-p enoxyacehc acid ester o- z- z r z - a m-~,(=u)mtiz Y
,-p epoxy-acetic acid ester o- z- z r z - m-C(=O)NHz am m a m v a a Y
s--p epoxy acetic acid ester o- r z z- z - m-C(=O)NHz ma m a ar v m a Y
n--p epoxy acetic acid ester o- z- z r z - enoxyacehc m-act o- r z Z z - -p m-C:(=NH)NHz epoxy-acetic act o- z- z z- z - -p m- )NHz epoxy-acetic act o- r z z- z - 3- p epoxy-aceticm-act z- z - 3 m-C;(=NH)NHz .iv mu -p o- z z epoxy-acetic acid o- z- z z- z - n- m- z -p epoxy acetic act o- r z z- z - enoxyacehc m- )NHz act o- r z z- z - -p m- z enoxyacehc act o- z- z z- z - -p m- z enoxyacehc act z- z z- z - 3- p epoxy-aceticm- z act o- z- z z- z - m-C(=O)NHz ....
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,--p epoxy acetic acid o- r z z- z - n- m--p epoxy acetic act o- z- z z- z - enoxye m- ~=NH)NHz ano o- z- z z- z - -p m- )NHz epoxy-a ano o-z- z z- z -p m-~;(=Nn)rrnz - epoxy-a ano o-z- z z- z 3- p m-- epoxy-a ano z- z z- z 3- - p epoxy-a m- z - ano o-z- z z- z n- epoxy a m-- -p ano o-z- z z- z enoxye m-C(=O)NHz - anol o-z- z z- z -p m=C~O~NHz - enoxye anol --o-z- z z- z -p m- )Nl~
- epoxy-a ano o-z- z z- z ,- p m- z - epoxy-a ano o-z- z z- z 3- - p epoxy= m=C(=O)NHz - ethanol o-z- z z- z n- epoxy- a m=C(=OjNF
- -p ano o-z- z z- z a m-C(=NH)NHz - y p epoxy-ethyl ...
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ether o-z- z z- z m-C(=NH)NHz - iva ua a w a a y -p enoxyethyl ether o-z- z z- z a m-C(=NH)NHz - Y
-p~enoxy=ethyl ether o-~Vz-Nriz H Ltiz-Ln(-Ntiz)-a m- z y 3-p epoxy-ethyl ether o-~Uz-Nriz H Ltiz-Lti(-Ntiz)-Memyi m- z Win,-u-pnenoxy-ethyl ether o-~Uz-NHz H C;Hz-C:H(-NHz)-lV1eT11y1 m- z tin-u-pnenoxy ethyl ether o-5U2 Hz H Ltiz-~t1(-Ntiz)-nnecnyi m- z N rnenoxyemyi ether o-5Uz-NHz H caiz-c:H(-ivtiz)-Metnyma-pnenoxyemyi m- z ether o-~U2 Hz H c:Hz-LH(-NHz)-nnemyi m- z N r-pnenoxyemyi ether o-5Uz-NHz H 1:H2-l:H(-NHz)-Metriyll:rl3- m- z phenoxyethyl ether o-SUz-NHz H laiz-l:H(-NHz)-Metnyt m-1:r13-V-phenoxyethyl ether o-5Uz-NHz H l;tiz-l;tl(-iVtlz)-MeTriy1 m-~.(=u)l~nz tin-u-phenoxyethyl ether o-r z z- - p m- z n eny -o-z- z z- _ -p m-~;(=~rt)mnz n eny _ o-z- z Z - -p m- z n eny -o-z- z z- - 3 P m-~:(=~n)rvtiz n enY
-o-r z z- - 3_ _ p eny m- z n -o'z- z z- - n_ eny m- =NHjNHz n _p -o-r z z- - p m- z n eny -o-z- z z- _ -p m=C(-O)~z n eny _ o-z- z z- _ -p m- z n eny _ o-r z z- - 3- p m- =O)NHz n eny -o-r z 2 - 3_ _ p eny m- z n -o-r z z- - n_ eny m-~~=u)mnz n _p -o-z- z z- - me p- z n -o-z- z 2 - -am p-~.~=~n~mnz n me -o-z- z H Z - -am p- z n me -o-z- z z- - 3-am p-n me -o-r z z - 3- p-C~=NH)NHz n -am - me o-z- z z- - n_ p- z n _am - me o-z- z z- - m p- z n me -o-r z z- - -am p-n me -o-z- z z- _ -am p-~;(=u)wnz n me _ o-z- z z- - 3-am p- z n me -o-r z z - s- p_ =p)NHz n -~
- me o-z- z z- - n_ p- z n _m - me o-r z z- - eny m- )NHz n -ammo-car - oxy is acid o- z- z z_ n - ieny m~NH)NHz -ammo-..,.-~
.
carboxylic acid o- z- z z- n - -p m~)NHz eny -ammo ..
carboxylic acid o- z- z ~I 3_~ainino m-C(=NH)NHz carboxylic acid O-~Vz-Nriz r~ t_;tiz-jai(-tsn)-trti3-u-pnenyi m-~:l=mti)Ntiz ammo carboxylic acid o-JVz-NHz H ~alz-tai(-tsn)-tsn-u-pnenyl m- z ammo carboxylic acid O-JUz-Nriz H uriz-uty-tsn)-rnenyi-ammo m- z carooxyiic acid o-~uz-Ntiz tm aiz-pat(-tsn)-~;i-pnenyi-ammo m- z carboxylic acid o-~uz NHz ri ~riz-pry-nn)-r-pneny-ammo m-~~=u)mriz carboxylic acid o-~uz-NHz tm ;riz ~;ty-rsn)-~ri3-pnenyi-ammo m-~,~=v)r~riz carboxylic acid O-JUZ-NHZ H l;tlz-l:ri(-tSn)-C;tl3-V-prieriYl-airilIlO m-l:(=V)lVtlz carboxylic acid O-JUZ-NH2 H Ltiz-Ltil-tsn)-tsn-u-pnenyi-ammo m-~l=v)ivriz carboxylic acid o-SOz-NHz H CHz CH(-Bn)-Methyl m-C(=NH)NHz phenoxy-acetic acid ester o-~O~-NHZ H CHz-CH(-Bn)-a m- z y -p enoxyacehc acid ester o- z- z H CHz-CH(-Bn)-a m- z y -p epoxy-acetic acid ester O-~Vz-NHZ H ~;tiz-jai(-tsn)-a m- z y 3-p epoxy-acetic acid ester o-SUz-NHz H laiz-cai(-tsn)-a m- z y j--p epoxy-acetic acid ester o-5Uz NHz H ~ai2 jai(-tsn)-a m- z y n_ -p epoxy acetic acid ester o- z- z H CHz CH(-Bn)-Methyl m- z Yhenoxyacetic acid ester o- z z H CHz-CH(-Bn)-a m- z y -p enoxyacehc acid ester o- r z H CHz-CH(-Bn)-a m- z y -p enoxyacehc acid ester o-aVz NHZ ti 1;t12-lal(-tSn)-a m-Y
3-p epoxy-acetic acid ester o-~Vz NHz H Lri2 c.;til-tsn)-Metnym:rij-u-pnenoxy m-~:~=u)ivriz acetic acid ester O-JUz-NHZ H ~tiz-~ti(-tsn)-Metnyi m-~.;1=~)mriz tsn-u-pnenoxy acetic acid ester o- z- z z- n - enoxyacehc m- z aci o- z- z 2 - n - -p m- 2 epoxy-acetic -aci o- z- z z- - n - -p m- 2 epoxy-acetic aci o- z- z z- - n - 3- p epoxy-aceticm-C(=NH)NHz aci o- z- z z- - n - 3- m- z -p epoxy-acetic acid o- i z Z n - n- m- z -p epoxy acetic aci o- z- z Z n - enoXyacetic rn-C(=O)NHz act o- z- z Z n - -p m- z enoxyacehc aci o- r z z- n - -p m- z enoxyacehc aci o- z- z 2 n - ,- p epoxy-aceticm-aci o- z- z 2 n - 3--p w.~ vy.au epoxy m- z acetic acid o- z- z Z n - n- m- z -p epoxy acetic aci o- z- z z- - n - enoxye m- NHz ano o- z- z z- n - -p m-V(=Nri)wriz enoxy-a ano o- i z -H - z- n - -p m- z enoxy-a ano o- z- z z- n - 3 p m- z enoxy-a ano o- r z z- - n - s- - p enoxy-a m- z ano o- z- z r n - n- enoxy a m-~l=~ri)Nriz -p ano o- r z z- - n - enoxye m- z ano o- z- z r - n - -p m- z enoxye ano -o- r z z- n - -p m- z enoxy-a anon o- r z z- - n - 3-p m enoxy-a ano o- z- z z- n - 3 p enoxy- m- z - a ano --o- z- z r - n - n- enoxy- a m- z -p anol o- z- z z- - n - a m-C(=NH)PHz y p enoxy-ethyl ether O-JVz-Nriz t~ Lriz-~ry-tsnl-memym.i-pnenoxyemy m- z ether O-JUZ-Ntl2 ti caiz-t,til-tin)-Memyi m- z r-pnenoxy-emyi ether o-JVZ-Nti2 ti c:riz-jai(-tsn)-nnetnymai3-pnenoxy- m- z ethyl ether O-5U2-Ntl2 ti caiz-gay-tsn)-nnemym:rij-u-pnenoxy- m-~;(=ivri)wriz ethyl ether O-5u2-Ntlz ti caiz-Ltil-tsn)-Memyi m-~l=mri)~ry tsn-u-pnenoxy ethyl ether o-~u2 lvttz t~ Ltiz-~;ri(-tsn)-nnemyi m- z rnenoxyemyi ether O-JUZ-Ntlz ti Ltiz ~ail-tsn)-Metnyma-pnenoxyecnyi m-~.l=u)r~riz ether O-JUZ-Nriz t~ Lti2 Vtil-tsn)-nneyu m-~(=u)~riz r-pnenoxyemy ether O-1Uz-NtiZ tl l;tl2-l:ril-tin)-MeLriyll:rij- m-phenoxyethyl ether O-5Uz-Ntiz t1 l;ti2-fall-tfn)-lVielllyll.rl3 m-l.;l=u)1Vr12 u-phenoxyethyl ether o-5uz-lVtiz ti l;ti2-C.;til-fin)-Mettlyl m-tin-u-phenoxyethyl ether O-5Uz-Ntiz ti l;ti2-l;tll-1x12-pnenyl m-COOCH,)-O-JVZ-Ntl2 2- z- -p m- z COOCH3)- eny o-5uz lvtlz ti ~aiZ-pail-Ltiz-r-pnenyi m-~l=ivri)rrriz COOCH3)-o-5u2 lvrlz ti caiz-Ltil-Lriz-3-p m- z COOCH,)- eny o-5V2-Nri2 tl Cal2-fail-(aiz-3_ m-COOCH,)- _p eriy O-5Vz-Nri2 ti Caiz-fail-lain-n_ m-COOCH,)- -p eriy O-JUz-Nriz tm atz-~;til-caiz-p m- z COOCH3)- eny o-~uz Ntiz tt Vtiz-aril-Vriz-m-pnenyi m- z COOCH,)-o-~uz-Nttz ti t;tiz-aril-~riz-r-pnenyi m-~l=u)mnz COOCH,)-o-~uz-Nttz ti t_;tiz-aril-~tiz~:ri3-pneny m-~:l=u)mriz COOCH,)-o-auz ivtiz m ;tiz-pail-~ti2-~ai3-u-pnenyi m-~.l=u)ivriz COOCH,)-o-~u2 Ntiz ti Vtiz-aril-uriz-tsn-u-pnenyi m- z COOCH3)-o-~uz-iVttz ti z- Z- 1 p-COOCH3)- me o- z- z z- z- -and me p-COOCH3)-o-~uz-lvrlz l:riz-pry-l:riz-r-anllme p- z COOCH3)-o-~uz-NHz ti l:riz-qty-~;tiz-l:ri,-anllme p-~~=mryvriz COOCH3)-o-~Uz-NHz H C;H2-C;H(-C;HZ-C;H3-V-amlme p-C:(=NH)NH2 COOCH,)-o- r z z- z- n- -am me p- z COOCH,)-O-JU2-1VI12 H 1x12-l:rl~-l;rly-Anllme p-~;~=uyvtiz COOCH,)-o-~uz-lvriz r z- -and me p- z COOCH,)-o-~uz-lvtiz r z- -am me p- z COOCH3)-o-JUZ-NHZ z- z- 3-ant me p-COOCH3)-O-JUZ-NHZ ri l;riz-l:ri(-l:riZ1:r13-U-anllme p-l:(=U)lVriy COOCH,)-O-JUZ-Ntiz H lalz-l:ri(-1;r12-tan-u-anllme p-COOCH3)-O-JVz-NHz H lair-l:ri(-C;tlz-Ynenyl-ammo-CarDOXyIICm- y COOCH3)- acid o-JVz NHz H 1x12-lal(-1x12-eny -amino m-COOCH3)- carboxylic acid O-JUZ-NHZ H l.al2-lal(-l.rlzr-pnenyl-ammo m-1.~=lVtlJlvriz COOCH3)- carboxylic acid o-SOz-NHz H C;Hz-C;H(-C;Hz-C;H3-phenyl-aminom-C;(=NH)NHz COOCH3)- carboxylic acid o-JVZ-NHZ ti l:Hy-l:H(-l:Hzl:ri3-u-pnenyl m-ammo COOCH3)- carboxylic acid o-~Uz NHz H l:Hz-1:H(-c:Hz-tsn-u-pnenyl m-1:~=mriJwriz ammo COOCH3)- carboxylic acid O-JVZ-NHZ H I:HZ l:H(-Calz-Yneriyl-ammo m-1:~=U)1Vr12 CarDOXynC
COOCH3)- acid O-JVZ-NHz ti l;Hy-l:H(-l:Hzl:l-prieriyl-ammom- y -COOCH3)- carboxylic acid O-JUZ-NHz ti laly-l:ri(-l;tlzr-pneriyl-ammo m-COOCH,)- carboxylic acid o-JVZ-NHZ H C.;HZ lal(-l;tlZ-1:ri3-prienyl-ammom-COOCH,)- carboxylic acid o-JUZ-Ntiz H C:HZ-Cal(-1x12-l:rij-U-prienyl-ammom-1~~=U)lVrlz COOCH3)- carboxylic acid o-JUy-NHZ H l:Hz l:ri~-l;tiZ-tiri-V-pnenyl-ammom-L(=UJlvriz COOCH3)- carboxylic acid o- Oz-NHz H C;Hz-C;H(-C;Hz-Methyl phenoxy-aceticm-C:(=NH)NHz COOCH,)- acid ester o-SOz-NHz H C;Hz-C;H(-C;Hz-Methyl (:1-phenoxyacehcm-(:(=NH)NHz COOCH3)- acid ester o- Oz-NHz H CHz-C:H(-CHz-Methyl >'-phenoxy-m- z acetic COOCH3)- acid ester o-JUZ-NHZ H 1;H2-lal(-lalZ-MeLtlyll:ri3-prienOXy-m-COOCHj)- acetic acid ester O-JUz-NHz H l:HZ-l:ry-l:riz-Memyll:ri3-U-pnenoxy-m-1:~=lrryvriz COOCH,)- acetic acid ester o-JVZ-Ntl2 H 1:ri2-l:ri(-1x12-Memyl tin-V-pnenOXym-l:(=lVr1)lVtlz COOCH3)- acetic acid ester o-SOz-NHz H (:Hz-LH(-C;Hz-Methyl Yhenoxyacehcm-C;(=U)NHz COOCH3)- acid ester o-SUz-NHz H C;Hz C;H(-C:Hz-Methyl C;1-phenoxyacehcm-C;(=V)NHz COOCH3)- acid ester o- z- z z- z- m- z au m ua a m am .~ v~maa a y -p enoxyacehc COOCH3)- acid ester O-JVZ-wtiz ri ~,riz-~;ril-~riz-Memy ~ri3-pnenoxy-m-~:l=vyvriz COOCH,)- acetic acid ester O-JVZ-wtiz ri ~;riz-~;ril-~;riz-nnetnym:ri3-V-pnenoxym- z COOCH3)- acetic acid ester o-~uz-Nriz r~ t,riz-~;til-~;ttz-a y n_ _p epoxy m- z COOCH3)- acetic acid ester o-SUz-NHz H CHz CH(-CHz-Yhenoxyacehc m-C(=NH)NHz acid COOCH,)-o-SOz-NHz H CHz CH(-CHz-Cl-phenoxy-acehcm-(:(=NH)NHz acid COOCH3)-o-SOz-NHz H CHz-CH(-CHzr-phenoxy- acehcm-C(=NH)NHz acid COOCH3)-o-SUz NHz H CHz-CH(-CHz-CHj-phenoxy-acehcm-C(=NH)NHz acid COOCH,)-o-SOz-NHz H CHz-CH(-CHz-CH3-U-phenoxy-acehcm-C(=NH)NHz COOCH,)- acid o-SOz-NHz H CHz-CH(-CHz-13n-U-phenoxy m- z acehc acid COOCH,)-o-SOz-NHz H CHz-CH(-CHzenoxyacehc aci m- z COOCH,)-o-SOz-NHz H CHz-CH(-CHz-Cl-phenoxyacehc m- z acid COOCH,)-o-SOz~VHz H CHz-CH(-CHz-p enoxyacehc m- z aci COOCH3)-o- Z z H CHz-CH(-CHz-3-p epoxy-acehc m- z aci COOCH3)-o- z- z H CHz CH(-CHz-3 -p epoxy acehcm- z COOCH3)- acid o- z- z H CHz CH(-CHz-Bn-U-phenoxy m- z acehc acid COOCH,)-o-JVz-Ntlz r z- enoxye ano m- z COOCH3)-o-JVz-Nriz ti Lriz-Lnl-unz-ul-pnenoxy-emanoim-~l=~ryrrriz COOCH3)-O-JUZ-Nriz rm aizway-~riz--p epoxy- a ano m- z COOCH3)-O-~Uz-Nriz ti ~tiz-c:ry-c:riz-3-p epoxy-a ano m- z COOCH,)-o-JVz-Ntiz ti ~;tiz cailwaizwai3-V-pnenoxy-emanoim- z COOCH3)-o-~Vz-Nriz ti LrirLril-Lnz-~n-V-pnenoxy m-~l=rrri)wriz etnanoi COOCH3)-O-JUZ-Nriz H (a12-fall-l;tl2-rnenoxyemanoi m-~l=VJr~riz COOCH,)-O-JV2 Ntl2 t1 l;rii l;tll-l~riz--p eriOXye ano m-COOCH3)-O-JUz-Nriz ri z z- -p epoxy-a ano m- z COOCH3)-O-JVZ-Ntl2 ti z 2- y-p epoxy-a ano m- y COOCH3)-O-JUZ-NHZ n z- z- ,- -p epoxy- m- z a ano COOCH,)-o-JVz-NtlZ Z- z- n- -p epoxy- m- z a ano COOCH3)-O-JVZ-NHZ ri ~tiz-aril-~riz-nnemyi pnenoxy-emyim- z COOCH,)- ether O-JUZ-NH2 tm ;tiz-pail-~;riz-nnetnyma-pnenoxyemyim- z COOCH,)- ether o-JUZ-NHZ ri 1:ri2-l:ril-l:rizlVlelllyl r-pnenOXy-eTIly1m-COOCH,)- ether o- z- z z- z- a Y 3 p enoxy- m- z COOCH,)- ethyl ether O-JUZ-Nriz ri ~riz-Sri(-~;riz-nnemym;rt3-u-pnenoxy-m-~;(=mtyvtiz COOCH3)- ethyl ether O-JUZ-lVri2 z- r a y n- -p enoxy m- z COOCH,)- ethyl ether ~''1U2-Nri2 ri ~'riz-Lri(-~'ri2-nnemyi rnenoxyemyim-~(=u~Nriz COOCH3)- ether O-JUz-Nri2 z- r a y -p enoxye m- z y COOCH3)- ether O-JU2-lVri2 z- z- a y -p enoxye m- z y COOCH,)- ether o-~uz-Nriz r~ ~riz-Sri(-~riZenemy ~ri3- m-~(=u~Nriz COOCH3)- phenoxyethyl ether o-~uz-Nriz r~ ~riz-Sri(-~riz-enemy ~rt3-u- m-~(=u~Nriz COOCH,)- phenoxyethyl ether o-~uz-mtiz t-~ ~tiz-Lti(-LriZMemy tsn-u- m-~(=uyvtiz COOCH3)- phenoxyethyl ether o-~uz-Ntiz t-~ Ltiz-~;ti(-trriz-pneny m-~(=mryvriz CHz-OH)-o-~uz-mriz t~ Ltiz-Lti(-~tiz-m-pnenyi m-~(=mryvriz CHz-OH)-O-JUz Ntiz ri ~riz-Sri(-~riz-r-pnenyi m-~(=NryNriz CHz-OH)-o-~uz-mtiz rt ~riz-~ti(-Ltiz~;ti3-pnenyi m-~(=mryvriz CHz-OH)-O-JUZ-Nriz ri ~:riz-Sri(-~:riz-~;ri3-u-pnenyl m- z CHz-OH)-O-JUz-Nriz z- z- n- -p eny m- z CHz-OH)-o-JUz-Nriz n ~tlz-~;t1(-~alz-pnenyi m- z CHz-OH)-O-~UZ-Ntl2 2- Z- -p eny m- z CHz OH)-O-JUz-Nriz z- z- -p eny m- z CHZ OH)-O-~uz-Nriz ri ~riz-Sri(-~riz-~ri3-pnenyi m-~(=u~Nriz CHz OH)-o-~uz-mriz z- z- 3- -p eny m- z CHz OH)-O-JUz-Nri2 t~ c:riz-Sri(-~tiz-~n-u-pnenyi m-~(=u~Nriz CHz-OH)-o-~uz-Ntiz t~ ~riz-Sri(-~riz-.mime p- z CHz-OH)-o-~uz-Ntiz ri ~riz-~ti(-~riz-m-amine p- z CHz-OH)-o-~uz Ntiz ti ~tiz-Sri(-~tiz-r-amnne p-~(=Nri~Ntiz CHz-OH)-o-~uz-Nriz ti ~riz-Sri(-~riz-~ri3-amine p-~(=Nri~Nriz CHz-OH)-o-~uz-Ntiz ti ~tiz-Sri(-~riz-~ri3-u-amine p-~(=NryNriz CHz-OH)-O-JUz-iVriz n ~riz-~ry-~riz-nn-u-anume p- z CHz-OH)-o-~uz-Nriz n ~riz-Sri(-~riz-amine p- z CHz OH)-O-JUz Nriz n ~riz Sri(-~riz-m-amine p- z CHZ OH)-O-JVz-Nriz n ~riz-Sri(-~riz-r-amine p- z CHZ OH)-o-auz iVtiz i z- 3 am me p- z CHz-OH)-o- z- z r z- 3- -am me p- z CHz-OH)-O-JUZ-Nriz ri ~riz-Sri(-~riz-tsn-u-amime p-~(=u)Ntiz CHz-OH)-o-~uz-wriz r~ ~riz-uti(-Vriz-rnenyt-ammo-carnoxyncm-u(=Nti)Nriz CHz-OH)- acid O-JU2-lVIlz h 1;ri2-lal(-l:riz-m-rnenyi-ammo m-u(=Nri)wriz CHz-OH)- carboxylic acid o-~uz-~riz n ~riz uri(-~riz-r-pnenyi-ammo m-~(=Nri)Nriz CHz-OH)- carboxylic acid O-JUZ-ivriz ri ~;riz-~:ri(-~riz-~ai3-pnenyi-armnom-t,(=~ti)Nriz CHz-OH)- carboxylic acid O-JUZ-ivriz ri z- z- 3- _p eny ammo m- z CHz-OH)- carboxylic acid o-~uz-Nriz n ~riz-Sri(-~riz-rsn-u-pnenyi m-~(=r~ri)wriz ammo CHz-OH)- carboxylic acid o-auz-Ntiz z- z- eny -ammo car m- z oxy is CHz-OH)- acid o-~uz Ntiz tm ;ttz-~:ri(-~;tiZ-p eny -ammo m- z CHz-OH)- carboxylic acid o-auz-Nriz n ~riz-uri(-uri2-p eny -ammo m- z CHz-OH)- carboxylic acid o-~uz-Ntiz ti ~riz-~ry-~riz~ri3-Pneny-ammo m- z CHz-OH)- carboxylic acid o-~uz-Ntiz t~ uriz-uri(-uriz-~ri3-u-pnenyi-ammom-~(=u)~riz CHz-OH)- carboxylic acid o-~uz-Ntiz ti uriz ury-~riz-~sn-u-pnenyi-ammom-~(=u)~riz CHz-OH)- carboxylic acid o-SOz-NHz H CHz-CH(-CHz-Methyl phenoxy-aceticm-C(=NH)NHz CHz-OH)- acid ester o-SOz NHz H CHz-CH(-CHz-Methyl Cl-phenoxyacehcm-C(=NH)NHz CHz-OH)- acid ester o-SOZ NHz H CHz-CH(-CHz-Methyl i'-phenoxy-m-C(=NH)NHz acetic CHz-OH)- acid ester o-~uz 1Vt12 H 1,ri2-l.tl(-1,t12-a Y j-p enoxy- m- z CHz-OH)- acetic acid ester o-~uz-ivriz m aiz-jai(-~aizmemyai3-u-pnenoxy-m-~.(=mri)~riz CHz-OH)- acetic acid ester o-~uz-Ntiz ti uriz-cai(-~:riz-Merry rsn-u-pnenoxym-~:(=r~ri)rrriz CHz-OH)- acetic acid ester o- z-NHz H CHz-CH(-CHz-a y enoxyacehc m- z CHz-OH)- acid ester o-SOZ NHz H CHz-CH(-CHz-a y -p enoxyacehcm- z CHz-OH)- acid ester o-SOz-NHz H CHz-CH(-CHza y -p enoxyaceticm- z CHz-OH)- acid ester o-~uz-Ntiz t~ ~riz-~:ri(-~riz-a Y s-p enoxy- m- z CHz-OH)- acetic acid ester o-~u~ NHz tm aiz-~:ri(-~rizenemy ~ri3-u-pnenoxym- z CHz OH)- acetic acid ester o-JUz NHZ H C;ri2-lal(-1x12-Merry tsn-u-pnenoxym-~(=u)~riz CHz-OH)- acetic acid ester o-SOz-NHz H CHz-CH(-CHz-Yhenoxyacetic m-C(=NH)NHz acid CHz-OH)-o-SOz-NHz H CHz-CH(-CHz-Cl-phenoxy-aceticm-C(=NH)NHz acid CHz-OH)-o-SOz-NHz H CHz CH(-CHz-r-phenoxy- aceticm-(:(=NH)NHz acid CHz-OH)-o-SOZ NHz H CHz-CH(-CHZCH3-phenoxy-aceticm-C(=NH)NHz acid CHz-OH)-o-SUz-NHz H CHz-CH(-CHz-CH3-U-phenoxy-aceticm-C(=NH)NHz CHz-OH)- acid o-z- z r z- n- -p epoxy aceticrii=C~~HjNHz aci CHz-OH)-O-JUy-Nt12 ~tiz-~ti(-~tiz-enoxyace c aci m- z OH)-o-SOz-NHz CHz-CH(-CHz- Cl-phenoxyaceLc m- z acid CHZ
OH)-o-SOz-NHz H CHz-CH(-CHz- F-phenoxyacehc m- z acid CHz-OH)-o-SUB H CHz-CH(-CHZ CH3-phenoxy-aceticm-C(=U)NHz acid CHz-OH)-o-SUZ-NHz H CHz-CH(-CHz- CH3-U-phenoxy m-C(=U)NHz acetic CHz-OH)- acid o-SUz-NHz H CHz-CH(-CHz- 13n-U-phenoxy m-(:(=U)NHz acetic acid CHz OH)-o-~uz-Ntiz ri ~riz-~nl-Lnz- rnenoxyemanoi m-~:(=mrywriz CHz-OH)-o-5u2 Hz t~ Ltiz-Lti(-Vtiz-m-pnenoxy-emanoim- z N
CHz-OH)-o-5Vz-Nriz t~ z- z- -p epoxy- a ano m- z CHz-OH)-o-~u2 Hz z- z- s-P epoxy-a ano m- z N
CHz-OH)-o-JUz Hz t1 Ltlz-Lt1(-Lt12 ~;ti3-U-pnenoxy-emanoim-~,(=mryvriz N
CHz-OH)-O-JU2-Ntlz r~ ~tiz-~ty-~nz n- -p epoxy a m- z ano CHz OH)-o-JUz-NHz ti z- z- enoxye ano m- z CHz OH)-o-5U2-Nriz tm :riz-Lril-Lriz-~-i-pnenoxyemanoim-~:(=~yvriz CHz-OH)-O-JUZ-NHz t1 2- z- -p erioxy-a ano m-CHz-OH)-O-5U2-Nt12 H 1;t12-lal(-l:riz-3 p erioxy-a m-ario CHz-OH)-o-5Uz-Nri2 ti t;riz tiz-3- -p epoxy- m- z Lti(-L a ano CHZ
OH)-O-JUZ-Ntlz tt ~riz-~nl-~nz- nn-u-pnenoxy- m- z emanoi CHz OH)-o-5u2 Hz H t;tiz-cai(-Ltiz-Memyi pnenoxy-etnyim-~(=Nri~wriz N
CHz-OH)- ether o-~uz-tvtiz ti ~tiz-Vti(-~riz-enemy m-pnenoxyeyum-~(=mryvriz CHz-OH)- ether o-~uz-Ntiz t~ catz-Lti(-Lttz-nnemyt r-pnenoxy-emyim- z CHz ether OH)-o-~uz tiz ti ~riz-pry-~riz nnemyi ~ri3-pnenoxy-m- z N
CHz-OH)- ethyl ether o-5u2 ttz tm aiz-Lti(-Ltiz a y 3- -p epoxy-m- z N
CHz-OH)- ethyl ether o-JUz-Ntiz H z z- a y n- -p epoxy m- z CHz-OH)- ethyl ether o-z- z z- z- a y enoxye y m-C(=O)NHz CHz-OH)- ether O-JUz-Nriz H t;tiz iz- nnetnym;i-pnenoxyemyim-~(=~~wriz Lti(-ca CHz-OH)- ether O-JUZ-Nri2 H caiz tiz-a y -p enoxye m- z Vti(-~ y CHz-OH)- ether o-JUZ-NHZ H 1:ri2-l;tl(-l;riz-MeTnyll;ti3- m-CHz-OH)- phenoxyethyl ether o-JUZ-NHZ H 1:ri2-1;t1(-1:ri2-Metnym;ti3-u- m-~(=u~wnz CHz-OH)- phenoxyethyl ether O-~Uz-Nttz H Ltiz-Vt1(-Vtlz-nnetnyi nn-u- m-~(=U~wriz CHz-OH)- phenoxyethyl ether o- z- z z- r P enY m-l:l=wri)wriz C(=O)-N-morpholino)-o-~uz-Ntiz tm _;tiz-l;til-l;riz-la-pnenyi m-l:l=wti)wriz C(=O)-N-morpholino)-o-~uz-Nriz r~ l:riz l;ril-l;riz-r-pnenyi m-l:l=wri)wriz C(=O)-N-morpholino)-O-JUz wtiz t~ l:riz-l;ril-l:rizl:ri3-pnenyi m-1:1=wri)wriz C(=O)-N-morpholino)-O-JUy-writ H lalz l;til-laiz-l;ti3-u-pnenyi m-l:l=wri)wriz C(=O)-N-morpholino)-O-JUz-Nriz ti l;tiz-l:ril-l:riz-tsn-u-pnenyi m-l:l=wri)wriz C(=O)-N-morpholino)-O-JVy-writ ti l:riz-l:ril-l:riz-pnenyi m-l:l=u)wriz C(=O)-N-morpholino)-O-JVZ-wtlZ ti l;rtz-l:ril-~riz-la-pnenyi m-l:l=v)wriz C(=O)-N-morpholino)-O-JUZ-Ntly ti l;tiz-l;ttl-c:riz-r-pnenyi m-1:1=u)wriz C(=O)-N-morpholino)-o-5Vz-wtlz t~ ~;t~z-l;til-l;tiz-l:rt3-pneny m-l,l=u)wtiz C(=O)-N-morpholino)-O-JVZ wtly tl lal2-fall-(:tiz-lalg-u-prienyl m-l.l=V)wrlz C(=O)-N-morpholino)-O-JUZ-writ t~ t,tiz-fail-l;tiz-nn-u-pnenyi m-1:1=u)wriz C(=O)-N-morpholino)-m me Jv 1aa aW .aW .aa~-W !~ a vl awy.u o- z- z a p- z Z- z-C(=O)-N-morpholino)-o-~uz-ivrtz tm ;rtzw:ryuatzwa-amime p-1,1=wti)wtiz C(=O)-N-morpholino)-O-~UZ-Nriz ri l:riz-l:ril-l:rizr-amime p-l:l=wri)wriz C(=O)-N-morpholino)-o-~uz-wry r~ l:riz-l:ril-l:riz-l:ri3-amnne p-1.1=lVr1)lvriz C(=O)-N-morpholino)-O-JVZ-wriz ri ~riz-l;til-l:riz-l:ri3-u-amime p-1,1=wn)wriz C(=O)-N-moipholino)-O-JVZ-writ ti 1.r12-l:rll-l:rlz-tsn-u-amime p-1.1=lVr1)1vr12 C(=O)-N-morpholino)-O-JUz-wriz tl lai2-l;tll-l:rlz-Anllllle p-lJl=V)wrl2 C(=O)-N-morpholino)-O-JVZ-wriz t~ t;tiz-l:ril-l.;riz-la-amime p-l:l=u)wriz C(=O)-N-morpholino)-o-auz wtiz ri 1.t12-1.111-1.r12-r-amime p-1:1=u)wriz C(=O)-N-more o mo -o-JVZ-rrHz ri ~riz-Sri(-MHz-LH3-amime p-~:~=Vyvtiz C(=O)-N-morpholino)-O-JVz-lvHz H ~riz-uH~-c:Hz-uH3-u-amime p-~l=u)wriz C(=O)-N-morpholino)-o-JUz-NHz H ~aiz-~:H(-~;Hztsn-u-amime p-t,(=Vyvtiz C(=O)-N-morpholino)-O-5Uz-NHz H l;Hz C:H(-l:Hz-Yneriyl-amln0-CarUOXyIICm-l:(=lVr1)lVtiz C(=O)-N- acid morpholino)-o-SU2lvHz H ~:Hz-LH(-c:Hz-ta-rnenyi-ammo m-~;~=wrywriz C(=O)-N- carboxylic acid morpholino)-o-~Uz-NHz H ~:r12 ~:rt(-t_;rlz-r-pnenyl-ammo m-~~=wryvriz C(=O)-N- carboxylic acid morpholino)-o-5Vz NHz H l;Hz-l:H(-l:Hzuric-pnenyi-ammom-~~=wriJwriz C(=O)-N- carboxylic acid morpholino)-O-SUz-NHz H l;Hz-l:H(-l;HZ-1:ri3-V-prienyl m-l;(=lVr1)lVrlZ
ammo C(=O)-N- carboxylic acid morpholino)-o-5uz lvHz H uHz-LH~-LHZrsn-u-pnenyi m-~~=Nrywriz ammo C(=O)-N- carboxylic acid morpholino)-o-5uz ivHz H LHz-uH(-LHz-rneny-ammo carnoxyncm-~~=u~wriz C(=O)-N- acid morpholino)-O-JUz-1VHZ H lalz-l;tl(-l;tiz-l:l-pneriyl-ammom-~.~=u)lvtlz C(=O)-N- carboxylic acid morpholino)-O-JVz-NHz H l:Hz-l:H~-l;Hz-r-pnenyl-ammo m-l:~=V)iVtlz C(=O)-N- carboxylic acid morpholino)-O-~Uz-NHz H ~:Hz-LHl-~-Hr~H3-Pneny-ammo m-~,~=vyvriz C(=O)-N- carboxylic acid morpholino)-O-JVz-NHZ H l:Hz t;H(-Calz-C:H3-V-prieriyl-ammom-l:~=VJlvrlz C(=O)-N- carboxylic acid morpholino)-O-JVz-NHz H (:Hz-C:H(-l;Hz-tin-V-pnenyl-ammom-~:~=u)iVtiz C(=O)-N- carboxylic acid morpholino)-o-SOz-NHz H CHz-CH(-CHz-Methyl phenoxy-aceticm-C;(=NH)NHz C(=O)-N- acid ester morpholino)-o-SOz-NHz H CHz-CH(-CHzMethyl Cl-phenoxyacehcm-C(=NH)NHz C(=O)-N- acid ester morpholino)-o-SUz-NHz H CHz-CH(-CHz-Methyl )~~-phenoxy-m-C(=NH)NHz acetic C(=O)-N- acid ester morpholino)-O-JVZ-lVriz ri l.,rlz-l.rl(-l.tlz-Memyi ~ri3-pnenoxy-m-l:(=lvtl)lvriz C(=O)-N- acetic acid ester morpholino)-O-JUZ-mri2 ri ~;riz ~;ri~-~:riz-memym:ri3-v-pnenoxy-m-~,1=mryvriz C(=O)-N- acetic acid ester morpholino)-~SO~-P -~ ~ CHz-CH(-CHZ-Methyl gn-O-phenoxym- =NH NHz ~ ~ ~
aceric aci ester -a moipholino)-o-SOz-NHz H CHz-CH(-CHz-Methyl Phenoxyacehcm-C(=U)NHz C(=O)-N- acid ester morpholino)-o-SOz-NHz H CHz-CH(-CHz-Methyl Cl-phenoxyaceticm-(:(=U)NHz C(=O)-N- acid ester morpholino)-o-SOz-NHz H CHz-CH(-CH2Methyl F-phenoxyaceticm-C(=U)NHz C(=O)-N- acid ester morpholino)-o-~uz-Ntiz m :riz-~til-~;tizmemym:ri3-pnenoxy-m-~l=~~wriz C(=O)-N- acetic acid ester morpholino)-O-JVZ-NHZ H MHz-aril-~riz-nnemyi ~ri3-u-pnenoxym-~l=v~wriz C(=O)-N- acetic acid ester morpholino)-o-~UZ Ntlz H ~riz-aril-~riz-enemy rsn-v-pnenoxym-~l=v~wriz C(=O)-N- acetic acid ester moipholino)-o-SOz-NHz H CHz-CH(-CHz-Phenoxyacehc m-C(=NH)NHz acid C(=O)-N-morpholino)-o- z- z H CHz-CH(-CHz-Cl-phenoxy-aceticm-C(=NH)NHz acid C(=O)-N-morpholino)-o- z-NHz H CHz-CH(-CHz-r~-phenoxy- aceticm-C(=NH)NHz acid C(=O)-N-morpholino)-o-S~NH2 H CHz-CH(-CHz-CH3 phenoxy-aceticm-(:(=NH)NHz acid C(=O)-N-morpholino)-o-~~-NH2 H CHz-CH(-CHz-CH3-U-phenoxy-aceticm-(:(=NH)NHz C(=O)-N- acid moipholino)-JV 111 1W .11 vi~-W 1J v 11 a v' avaa~W
o- z- z n- -p epoxy aceticm- z z- z- aci C(=O)-N-morpholino)-o-SOZ NHz H CHz CH(-CHz-Yhenoxyacehc m-C(=U)NHz acid C(=O)-N-morpholino)-o-SOZ-NHz H CHz-CH(-CHz-Cl-phenoxyaceticm-C(=U)NHz acid C(=O)-N-morpholino)-o- z- z r r -p enoxyacetic m-C(=O)NHz acid -.- ~.
C(=O)-N-morpholino)-o-SOz-NHz H CHZ CH(-CHz-CH3-phenoxy-aceticm-C(=U)NHz acid C(=O)-N-morpholino)-o- z-NHz H CHz-CH(-CHz-CH3-U-phenoxy m-C(=U)NHz acetic C(=O)-N- acid motpholino)-o-SOz-NHz H CHz-CH(-CHz-Bn-U-phenoxy m-C(=U)NHz acetic acid C(=O)-N-morpholino)-O-JUz-Nriz H ~riz-~nl-~nz-rnenoxyemanoi m-~l=~rywriz C(=O)-N-moipholino)-.
O-JVZ-NHZ H 1:H2-l;Hl-l:riz-l:l-pneriOXy-elllanolm-l:l=lVtlJlVtlz ' C(=O)-N-morpholino)-o- z- z z- z- -p enoxy- et in~(=lQHjRHz iano C(=O)-N-morpholino)-O-JVz NHz H l;Hz-l:Hl-l;Hz-1;H3-pneriOXy-eTtlanolm-l:l=1VH)lVHz C(=O)-N-morpholino)-O-JUZ-NHZ H C:HZ-l;Hl-1:H2-1:H3-V-prienoxy-etrianotm-~:l=1VH)1VH2 C(=O)-N-morpholino)-O-JUZ-NHZ H l.Hz-C:HI-(:HZ-lin-V-pnenOXy m-l:l=1VH)1VH2 elllanol C(=O)-N-morpholino)-O-JVZ-NHq H l:Hz-l:Hl-l;Hz-YnenOXyeTClan01 m-l.;l=V)lVHy C(=O)-N-morpholino)-O-JUz-NHy H l:Hz-l:Hl-l;HZ-l;l-prieriOXyelllan0lm-l.;l=V)iVH2 C(=O)-N-morpholino)-o- z- z z- z- -p enoxy-a ano m- z C(=O)-N-morpholino)-O-5Uz NHZ H l:Hz-(:Hl-l:Hz~H3-pnenoxy-etnanoim-~l=v)~Hz C(=O)-N-morpholino)-o-5Uz-NHz H ~:HZ LHl-~:Hz-LH3 U-pnenoxy- m-~:l=v)~Hz emanoi C(=O)-N-morpholino)-o-SUz NHz H ~:Hz-LHl-~;Hz-tsn-u-pnenoxy- m-~:l=v)mHz emanoi C(=O)-N-morpholino)-o-JVz-Nriz H ~:Hz LHl-~:HZ-nnemyi pnenoxy-emyim-~,l=mH)mHz C(=O)-N- ether morpholino)-O-~Uz-NHz H ~:HZ-~:Hl-~:HZ-Metnyma-pnenoxyemyim-~.~=mri)mriz C(=O)-N- ether morpholino)-o-~uz-lvHz H LHZ-LHl-LHZ-Memyi r-pnenoxy-emyim-~l=~H)mHz C(=O)-N- ether morpholino)-o-~uz NHz H ~HZ-~Hl-~HZiviemyi ~H3-pnenoxy-m-~l=mH)mriz C(=O)-N- ethyl ether morpholino)-o-~Uz-NHz H 1.:H2-(:Hl-1;H2-Metnym:H3-u-pnenoxy-m-~:l=r~ri)r~Hz C(=O)-N- ethyl ether morpholino)-o-~uz-mHz H t~HZw:HI-t.HZ-mecnyi ~sn-v-pnenoxym-~.l=mH)mnz C(=O)-N- ethyl ether morpholino)-O-JUz-NHz H l:Hz-l;Hl-liH2-lVleitlyl YrieriOXyeTriylm-l:l=V)lVHz C(=O)-N- ether morpholino)-O-JUZ-NHZ H l:Hy-l:Hl-1;H2-nnemyi m-pnenoxyemyim-~l=v)~Hz C(=O)-N- ether morpholino)-O-JUZ-NHZ H t,Hz-c:Hl-~;Hz-nnemyi r-pnenoxyetnyim-~l=~)mHz C(=O)-N- ether morpholino)-O-1Uz-NHZ H 1:H2-l:Hl-1;H2-nnemyi ~H,- m-~l=v)mHz C(=O)-N- phenoxyethyl ether morpholino)-O-JUZ-NHZ H C;Hz-l:Hl-1:H2-MetClyll:Hg-V- m-C(=O)-N- phenoxyethyl ether more o mo -o- z- z z_ z_ a y n_ - m-C(=O)NHz ... u. . ..~
~, C(=O)-N- phenoxyethyl ether moipholino)-o-SUZ-NHZ H 1;H2-l:H(-1:ri2-phenyl m-CHz-S(O)z-CH, o-5Vz-NHz z- z- -p eny m- z CHz-S(O)z-CH3 o-~Uz-NHz H C:HZ-C.;H(-C;HZ-r-pnenyi m-~(=rVri)rrriz .
CHz-S(O)z-CH3 o-~U2 NHz ri UriZ c:ri(-uHz-3-p eny m- z CHz-S(O)z-CH3 o-~V2 NHz ri z z- 3- -p eny m- z CHz-S(O)z-CH3 o-SUZ-NHZ H 2_ 2_ n_ _p eny m- z CHz-S(O)z o-5Uz-NHz H l:riz-t;ri(-C:riz-phenyl m-~;(=u)rVriz CHz-S(O)z-CH3 o-5Vz NHz H l:riz-C.;ri(-1:H2--p eny m-CHz-S(O)z o-5Uz-NHz H ~riz-c:ri(-~riz-r-pnenyi m- z CHz-S(O)z-CH3 o-5Uz-NHZ H ~riZ-Sri(-~riz-~ri3-pnenyi m-~(=u)mriz CHz-S(O)z-CH3 o-5Uz-NHz H Lriz-Lri(-~riz-~ri3-u-pnenyi m- z CHz-S(O)z-CH3 o-SUZ NHZ H C:riz l;H(-l:riz-n_ _p eny m- z CHz-S(O)Z
o-SUZ NHz H CJHz t;ri(-c,riz-m me p- z CHz S(O)z o-~UZ NHz H C:HZ c:H(-t;Hz_-am me p- z CHz-S(O)z-CHj o-SUz-NHz H C:Hz-C:H(-t.riz_-am me p- z CHz S(O)z CH, o-SUz-NHz H c:Hz-c:ri(-C:riz-3-am me p- z CHz S(O)Z
CH, o-SUz-NHz H c:riz Lri(-c:riz-3- -am me p- z CHz S(O)z CH, o-5U2-NHZ H C:HZ-l:H(-(:HZ-n_ -am me p-CHz S(O)Z
CH, o-SU2 NHz H z z- m me p- z CHz-S(O)z-CH3 o-5U2 NHz H c:riz t;ri(-c:riz-W -amtme p-l.(=V)1Vt12 CHZ S(O)z CH, o-5Uz NHz ri C:Hz-C:ri(-l;riz-r-anllme p- z CHz-S(O)z-CH3 O-5Uz-Nriz H c:riz-Sri(-~riz-~ri3-amime p- z CHz-S(O)z-CH3 o-5uz-NHz ri Lriz-Sri(-~riz-~ri3-u-amime p- z CHz-S(O)z-CHj o-5Uz-Nriz H (:Hz-Lri(-Lriz-tsn-u-amlme p- z CHz-S(O)i o-SUz NHz H Lriz c:ri(-~ri2-rnenyi-ammo-carooxyiicm- z CHZ S(O)z-CH3acid o-SUz-NHz H (_;riz-cJri(-LHz-eny -ammo m- z CHz-S(O)z-CH3carboxylic acid O-SUZ-NHZ H l;riz-l:ri(-1:H2-r-pnenyi-ammo m-~~=rrri)ivriz CHz-S(O)z-CH3carboxylic acid o-SUZ NHz H c:riz Lri(-~;riz-3 p eny -ammo m- z CHZ S(O)z-CH3carboxylic acid o-SUz-NHz H C:HZ ~;H(-~:riz-3- -p eny ammo m- z CHz-S(O)z-CH,carboxylic acid o- z- z z- z- n- -p eny ammo m-l:l=~rywriz CHz-S(O)z-CH,carboxylic acid o-~uz-Ntiz ti laiZ l:ri(-laiz-Yneny-ammo carnoxyucm-l:l=u~Nriz CHz-S(O)Z acid CH, o-~uz-Nriz ri l:riz-l:ril-l:riz-m-pnenyi-ammo m-l:l=uJ~riz CHz-S(O)z-CH,carboxylic acid o-~u2 Nriz ri l:riz-l:ril-~riz-r-pnenyi-ammo m-~l=u~r~riz CHz-S(O)z-CH3carboxylic acid O-JVZ-lVtlz H 1x12-fall-lalz-l:ri3-pnenyi-ammom- z CHz-S(O)z-CH3carboxylic acid O-JVZ lVriz tm :riz-l:ry-~riz-l:ri,-u-pnenyi-ammom- z CHz-S(O)z-CH3carboxylic acid O-JVZ-Nriz rl 1a12-l:ril-1;ri2-n- -p eny -ammo m-CHz-S(O)z-CH3carboxylic acid o- Uz-NHz H CHz-CH(-CHz-a y p enoxy-aceticm- z CHz-S(O)z-CH3acid ester o- z- z H CHz-CH(-CHza y -p enoxyaceticm- z CHz-S(O)z-CH3acid ester o- z- z - ~ CHz-CH(-CHz-a y -p enoxy- m- z - acetic CHz-S(O)z-CH3acid ester o-SVZ-NriZ z- z- a y 3-p enoxy- m- z CHz-S(O)z-CH3acetic acid ester o-5Uz NHz H Ltiz-fail-laiz-Memyi l:ri3-u-pnenoxy-m-~l=r~ry~riz CHz-S(O)z-CH3acetic acid ester o-~uz-NHz ti l:riz-l:ril-l:riZMemyi rsn-u-pnenoxym- z CHz-S(O)z-CH3acetic acid ester o ~z-NHz H CHz-CH(-CHZMethyl Yhenoxyaceticm-C:(=U)NHz CHz-S(O)z-CH3acid ester o- z- 2 H CHz CH(-CHz-Methyl Cl-phenoxyaceticm-(:(=U)NHz CHz-S(O)z acid ester o- Z z H CHz-CH(-CHz-Methyl l'-phenoxyacehcm-(:(=U)NHz CHz S(O)z-CH3acid ester o-JVZ-NriZ H caiz-fail-laiznnemymai3-pnenoxy-m-l.l=u~~tiz CHz-S(O)z-CH3acetic acid ester o-JUZ-NHz H 1;t12-l:ril-1;ri2-mecnyll~ri3-u-prienoxym-l:l=VJ1Vr12 CHz-S(O)z-CH3acetic acid ester O-JU2-NH2 ti caiz lail-laiz-nnecnyi tsn-u-pnenoxym- z CHz-S(O)z-CH3acetic acid ester o-SOz-NHz H CHZ CH(-CHz-Yhenoxyacehc m- z acid CHz-S(O)z o- z-NH2- H z z- -p enoxy-acetic m- z - aci CHz-S(O)z-CH3 o- z-NHz H z- Z -p enoxy- aceticm- z aci CHz-S(O)z-CH3 o- Uz-NHz H CHz-CH(-CHz-CH3-phenoxy-acericm- z acid CHz-S(O)z-CH3 o- z-NHz H CHz-CH(-CHz-CH3-U-phenoxy-aceticm- z CHz-S(O)z-CH3acid o-SOz NHz H CHz-CH(-CHz-n- -p enoxy aceticm- z aci CHz-S(O)z-CH3 o-SOz-NHz H CHz-CH(-CHz-Yhenoxyacetic m- z acid CHz S(O)z-CH3 o-SOZ NHz H CHz-CH(-CHz-Cl-phenoxyaceticm-(:(=U)NHz acid CHz-S(O)z-CH3 o-SOz-NHz H CHz-CH(-CHz-1-phenoxyacetic m-C(=U)NHz acid CHz-S(O)z-CHj o-SOz-NHz H CHz CH(-CHz-CH3-phenoxy-aceticm-C:(=U)NHz acid CHz-S(O)z-CH3 o-SOz-NHz H CHz-CH(-CHz-CH3-U-phenoxy m-C(=U)NHz acetic CHz-S(O)z-CH3acid o-SOz NHz H CHz-CH(-CHz-tan-U-phenoxy m-C:(=U)NHz acetic acid CHz-S(O)z-CH3 o-z- z z- z- enoxye iano .~ ....~...
m-CHz-S(O)z-CH3 o-z- z z- z- -p m~)~z enoxy-a ano ,.,.
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u.
CHz-S(O)z-CH3 O-JUz-Ntiz ti ~riz-~ry-~;tizr-pnenoxy- m-~~=ivryNriz emanoi CHz-S(O)z-CH, o-JVz-Nriz t~ ~riz-Lti(-utiz-t;ti3-pnenoxy-emanoi m-~~=NriJNriz CHz-S(O)z-CHj O-JUz-Nriz t~ uriz-uty-urtz-uti3-u-pnenoxy-emanoi m-u~=NryNriz CHz-S(O)Z
CH, o-~uz-Ntiz ri urtz-ur1(-uriz-~sn-u-pnenoxy m-~(=mryNriz emanoi CHz-S(O)z-CH3 o-~uz-Nriz ti ~riz ~ry-~ry-enoxye m- z ano CHZ S(O)z-CH3 o-~uz-Nttz ti ~riz-pry-~riZm-pnenoxyemanoi m- z CHz S(O)z-CH3 o-~uz-Ntiz t1 t_:rizw;tll-~;tlzr-pnenoxy-etnanoi m- z CHz S(O)z-CH3 O-JUz-Ntiz ri l:riz-l:ri(-l;riz-3-p m- z enOXy-a ano CHz-S(O)z-CH3 o-~Uz-Ntiz ti z- z- 3- m- z _p enoxy-a ano CHz-S(O)z-CH3 O-~Uz-Nriz z- z- n- m- z -p enoxy-a ano CHz-S(O)z-CH3 o-auz-Ntiz m ;tiz ~;ti~-~:riz-nnewyi m-~.~=mriyvriz pnenoxy-emyi CHz-S(O)z-CH3ether o-JVz-Nriz t1 Ltiz-~;ti(-caiz-nnetnym;i-pnenoxyemyi m-~:~=mryvriz CHz-S(O)z-CH3ether o-JVZ tlz ti Ltiz-~ai~-~;tiz-a m- z N y -p enoxy-a y CHz-S(O)z-CH3ether o-~u2 riz ti l:riz-~;ti(-lJriz-Memym;ti3-pnenoxy- m- z N
CHz-S(O)z-CH3ethyl ether O-~Uz-Ntiz ti Lti2 Lti(-caiz-Metnyi m- z ~ri3-u-pnenoxy-CHz-S(O)z-CH3ethyl ether O-JUz-NHZ H Calz-lal(-1:ri2-rnetnyi m- z rsn-u-pnenoxy CHZ S(O)z-CH3ethyl ether O-JUz-Ntlz ti ~riz-~ry-~riz-Memyi m-~,~=a rnenoxyemyi yvriz CHz-S(O)z-CH3ether O-~uz-Nriz ti Ltiz-pat(-~aiz-nnemymu-pnenoxyerrryi m-~:~=uyvriz CHz-S(O)z-CH3ether o-~u2 tlz tm aiz-~;ti(-~aiz-nnetnyi m- z N r-pnenoxyetnyi CHz-S(O)z-CH3ether o-JUz-Ntlz t1 lalz-l;tl(-l:rlz-MeTriy1 m-~;r13=
CHz-S(O)z-CH3 phenoxyethyl ether o-JUz-Nt12 ti laiz-1:r1(-taiz- nnemyi ~n3-u- m- z CHz-S(O)z phenoxyethyl CH, ether O-JVz-Nriz ti l:riz l=rl(-1;ri2- a y n- m- z ~
CHz-S(O)z-CHjphenoxyethyl ether o-JUz-Nriz t1 caiz-~;ti(-~;tiz-pneny m-~:~=mryvriz hexane)-o-~u2 tiz ti z- z- -p m- z N eny hexane)-O-~Uz-Nriz ti ~tiz-~ri~-~riz-r-pnenyi m-~~=Nriyvriz hexane)-o-JUZ-Nri2 t1 l:rlz-~;tt(-~atz-3-p m- z eny hexane)-o-~uz-Ntiz t~ trtiz ~ti~-~tiz-~;ri3-u-pnenyi m-~.~=mryvriz hexane)-O-~uz-Nriz n taiz-pry-~ri2-tsn-u-pneny m-~~=ivryvriz hexane)-o-~uz-Nriz ti ~riz-~ti~-~tiz-pnenyi m-~~=u~Nriz hexane)-o- z- z z- z- -p eny m_ v~ v~a.a hexane)-o_ z_ z - z_ z_ -p eny m-C( O)NHz .. . ..
hexane)-O-JVz-NHz ri l:riz-l:ri(-l:riz-c:ri3-pnenyi m-~(=u~wriz hexane)-O-JVZ-NriZ ri I:HZ l;H(-l:Hz-C;H3-u-prienyl m-hexane)-O-JUz-Nriz ri l:riz-l:ri(-l:nz-n- -p eny m- z hexane)-o-~uz-NHz ti lain lai(-litiz-me p-hexane)-o-~uz-NHz n z z- -am me p- z hexane)-O-lu2-NHZ ti lalZ l;tl(-lain-r-allllllle p-l.(=lVr1)1V112 hexane)-O-JUZ-NHz H l:Hz-liri(-1x12-1,ri3-anlllIle p-l;(=1Vri)Nriz hexane)-o-~uz-NHz ri l:riz-l:ri(-~riZl:ri3-u-anume p- z .
hexane)-O-JUz NHZ H l:Hz-l:H(-l:Hz-tSn-u-amlme p-hexane)-O-JV2-NHZ H l:Hz l:H(-C;HZ-m Ille p-hexane)-O-JUZ-NHZ H 1:H2-C;H(-l:riZ-l;l-anllme p-hexane)-o-JVz-Nriz H z- z- -am me p- z hexane)-o-~Vz-NHz H l:Hz-c:H(-~riz-l:ri3 amtme p-1:(=u~~riz hexane)-o-5Uz-NHz H z- z_ 3_ -ant me p- z hexane)-O-JUZ-NHZ H l;Hz l:H(-1:H2-tan-u-anllme p-l:(=V)lVriy hexane)-o-~Vz-NHz H z- z- eny -ammo-car m- z oxy is hexane)- acid o-JVz-NHZ H 1:H2-l;H(-C;HZ-l:l-Yrienyl-amlIlom-l:(=LVri)iVriz , hexane)- carboxylic acid o-JVZ NHz H MHz-1:H(-l:Hz-r-pnenyi-ammo m-1:(=wrywriz hexane)- carboxylic acid o-JVZ-NHZ H l;Hz-l;H(-liriz_1x13-prienyl-ammom-l.;(=lVriJ1vt12 hexane)- carboxylic acid O-5Vz-NHZ H I:HZ l;H(-I:HZ-1;ri3-u-prieriylm-l;(=iVtl)lvrlz ammo hexane)- carboxylic acid o-5uz-NHz H l:Hz-1;H(-llHz-tsn-u-pnenyi m-1:(=Nryvriz ammo hexane)- carboxylic acid o-~uz-NHz H l:Hz-l:ri(-l:riz-rnenyi-ammo carnoxyncm-1:(=l.r~wriz hexane)- acid o-aVz-NHz H ~riz-l:ri(-~rizla-pnenyi-ammo m- z hexane)- carboxylic acid o-~uz-NHz H l:riz-l:ri(-l:riz-r-pnenyi-ammo m- z hexane)- carboxylic acid o-aVz-NHz H l:riz-l:ri(-l:Hz-l:ri3-pnenyi-ammom-1:(=u)rrriz hexane)- carboxylic acid o-~uz-Ntiz H l:riz-1:H(-c:Hz-l:ri,-u-pnenyi-ammom- z hexane)- carboxylic acid o-~uz-NHz H ~riz-c:ri(-l:Hz-tsn-u-pnenyi-ammom-1:(=u~wriz hexane)- carboxylic acid o-SOz-NHz H (:Hz-(:H(-C;Hz-Methyl phenoxy-aceticm-C;(=NH)NHz hexane)- acid ester o-SOZ NHz H CHz-CH(-(:Hz-Methyl (:1-phenoxyacehcm- z hexane)- acid ester li-J
o- r z z- r et y -p enoxy- m- z acetic hexane)- acid ester O-JV2-Nri2 tt y aiz-Ltil-Ltiz-nnemymai3-pnenoxy-m-t,l=~rywriz hexane)- acetic acid ester O-JUz-Ntiz ri t,riz aril-~riz-nnemymai3-v-pnenoxy-m-~l=r~ryvriz hexane)- acetic acid ester O-JV2-Ntl2 m ;ttZ tail-~riz-a y n- -p enoxy m- z hexane)- acetic acid ester o-SOz-NHZ H CHz-CH(-CHz-Methyl Phenoxyacehcm- =U z hexane)- acid ester o-SOz~ H CHz-CH(-CHz-a y -p enoxyacehcm- =U z hexane)- acid ester o-SOz-NHz H z- z- a y -p enoxyacehcm- z hexane)- acid ester O-JUZ NHz t~ ~riz-~til-~tiz-nnemym;ri,-pnenoxy-m-~l=~~~riz hexane)- acetic acid ester o-~uz Nri2 m aiz-~ayuaiz-Metnyi t.ti3-v-pnenoxym- z hexane)- acetic acid ester O-JUz Nriz ri ~riz-~ry-~rizmewyi rsn-u-pnenoxym- z hexane)- acetic acid ester o-~Oz-NHZ H CHz-CH(-CHz-Yhenoxyaceric m-(:(=NH)NHz acid hexane)-o-SOz-NHz H CHz CH(-CHz-Cl-phenoxy-aceticm- z acid hexane)-o-SOz-NHz H CHz-CH(-CHz-1~'-phenoxy- m-(:(=NH)NHz acetic acid hexane)-o-SOZ-NHz H CHz-CH(-CHZCH3-phenoxy-aceticm- z acid hexane)-o-SOz-NHz H CHz-CH(-CHz-CH3-U-phenoxy-aceticm-C:(=NH)NHz hexane)- acid o- Oz-NHz H CHZ CH(-CHz-Bn-U-phenoxy m-C(=NH)NHz acetic acid hexane)-o-SOz-NHz H Z z- enoxyacehc aci m- z hexane)-o- UZ~TH2 H z- z- -p enoxyacehc m- z -- aci J
hexane)-o- Oz-NHz H CHz-CH(-CHz-F-phenoxyacehc m-C;(=U)NHz acid hexane)-o-SOz-NHz H r r 3-p enoxy-aceticm- z aci hexane)-o-SO~THz H z- r 3- -p enoxy acericm- z hexane)- acid o- ~lHz H CHz-CH(-CHZtan-U-phenoxy m-(:(=U)NHz acetic acid hexane)-o-~uz-Nriz ti ~nz-~ril-~nz-enoxye ano m- z hexane)-o-~uz-Nttz 11 l:rizW :rilW:rtz~:1-pnenoxy-emanolm- z hexane)-O-JVz-Nriz z- i -p enoxy- a ano m- z hexane)-o-~u2 Ntiz t~ qty-~ry-~ry-iris-Pnenoxy-ecnanoim-~l=~ryr~riz hexane)-o-~uz-Ntiz t~ Ltiz-~til-~riz-~ri3 u-pnenoxy-emanoim-~l=~ryr~riz hexane)-o-~uz-Ntiz t~ ~tiz-~ry-~riz-tsn-u-pnenoxy m- z emanoi hexane)-O-JVZ-Ntlz n ~-rir~-ril-~-riz-YneriOXyeinan0l m-hexane)-o-~uz Ntiz ti ~tiz-~ry-~rtz-m-pnenoxyemanoi m-~l=~~mriz hexane)-o-~uz-Ntiz m ay--ry-t-riz-r-pnenoxy-emanoim-~:l=~~mriz hexane)-o-z- z H m-C(=O)NHz v11 vllt-VllVll z- z- 11 3-p enoxy-et anol hexane)-O-JUz-Nriz ri ~;riz-t:ril-taiz-Lti3-u-pnenoxy- m-t:l=u)ivriz emanoi hexane)-O-JUZ-wriz ri ~riz-~:ril-taiz-tsn-u-pnenoxy- m-t_;l=u)wtiz emanoi hexane)-O-JUZ-wriz ri ~:riz-aril-taiz-Metnyi m-t:l=ivti)ivtiz pnenoxy-emyi hexane)- ether O-JVZ tiz rm _;riz-aril-~tiz-Memyi m-ul=ivri)Nriz N ta-pnenoxyemyi hexane)- ether O-JU2-lVriz Lriz-~-ril-Lriz-Memyi m-~:l=ivri)Nriz r-pnenoxy-emyi hexane)- ether O-JUZ-Ntiz z- z- a m- z y ,-p enoxy-hexane)- ethyl ether O-JUz-Nriz ri ~;riz-tail-t:rizMemyi m-t:l=ivri)ivriz ~ri3-v-pnenoxy-hexane)- ethyl ether o-JUz-iVriz z- z- a m- z y n--p enoxy hexane)- ethyl ether o-SOz-NHz z- z- a m- z y enoxyet y hexane)- ether O-JUz-lVriz ri ~-riz-~-ril-t-riz-Metnyi m-~:l=u)Nriz ta-pnenoxyemyi hexane)- ether O-JUz-Ntiz ri caiz-aril-~riz-a m- z y -p enoxye y hexane)- ether O-JUz-Ntlz r1 t:riz-fall-1;ri2-lVlelllyi m- z 1;ri3-hexane)- phenoxyethyl ether O-JUz-Nriz ri lalz-l:ril-1:ri2- MeTllyi l;rij-u-m-l:l=u)lVriz hexane)- phenoxyethyl ether o-au2 tiz rm ;riz-~;nl-t:ri2 memyi rsn-u- m-~l=u)rVriz iv hexane)- phenoxyethyl ether o-~uz-Nriz ri t:riz-t.ril-uriz-pnenyi m-~l=ivri)ivriz (HO-phenyl))-o-~uz-mtiz ti taiz-~atl-~aiz_-p m- z eny (HO-phenyl))-o-~uz-Ntiz t~ t:riz-t:rilw:riz-r-pnenyi m-~.l=mri)mriz (HO-phenyl))-o-~uz-lVtiz ti taiz-Ltil-taiz-Lti3-pnenyi m-t:l=ivri)wtiz (HO-phenyl))-o-~uz-Ntiz z- r s- m- z -p eny (HO-phenyl))-o-~u2 riz ri taiz-~;til-Ltiz-tsn-u-pnenyi m-t:l=ivri)ivriz N
(HO-phenyl))-o-~uz-wiiz n z z- p m- z eny (HO-phenyl))-O-JUz-ivriz ri taiz-~:ril-t:riz-ta-pnenyi m-~,l=u)ivriz (HO-phenyl))-O-JUz-Nriz ti z- z -p m- z eny (HO-phenyl))--o-z- z z- z_ 3-p m-C(=O)~z eny W
(HO-phenyl))-o-~uz riz m aiz-~:ril-~riz~:ri3-u-pnenyi m-~.l=u)ivriz iv (HO-phenyl))-o-~uz-ivtiz ti t:riz-t:ril-t:riz-tsn-u-pnenyi m-t.l=u)ivriz (HO-phenyl))-O-JUZ-ivriz ri ~:riz-~:ril-t.riz-Amime p-t.l=ivri)ivriz (HO-phenyl))-o-~uz-ivriz ti ~tiz-tail-t:riz-la-anume p-t:l=rrri)ivriz (HO-phenyl))-o-~uz tiz m ;riz-aril-~riz-r-amime p-t:l=rrri)ivriz N
(HO-phenyl))-o-~uz-Ntiz r~ ~nz-aril-~riz-t:ri3-anume p-~l=rVri)ivnz (HO-phenyl))-n- z- z z- r s--am ..~ .,..,.,.
me p-(HO-phenyl))-c- r z z- z- n- p- NHz -am ._,~ .,.., me (HO-phenyl))-O-JUZ-NHZ H l;Hz-l:H(-l:HzAnllme p-l:(=U)Nriz (HO-phenyl))-o-JUZ-NHZ z- z- -ant p-me (HO-phenyl))-o-JVz NHz H c:Hz-1;H(-l;rlz-r-anllme p-~:(=v)Nrtz (HO-phenyl))-O-JUz-NHZ H l:HZ-l;tl(-l;Hz-1;H3-anllme p-(HO-phenyl))-O-JUz-Nriz ri l.;rlz-l;ti(-l;riz-1x13-u-anllme p- z (HO-phenyl))-O-JUZ-NHZ ti 1:H2-l:H(-1;r12-tsn-v-anllme p-L(=V)1vr12 (HO-phenyl))-o-5U2 NHz H 1;H2 1:H(-l:HZ-rnenyl-ammo-carnoxync m-1:(=Nri)Nriz (HO-phenyl))-acid o-~uz-NHz H l:HZ-1.;H(-l:HZ-1:1-rnenyl-ammo m-~;(=lvri)lvriz (HO-phenyl))-carboxylic acid o-JVz-Nriz H l;tiz-~H(-l:HZ-r-phenyl-ammo m- z (HO-phenyl))-carboxylic acid o-5Uz-NHZ H 1:H2-l;H(-1;t12-1x13-phenyl-ammo m-(HO-phenyl))-carboxylic acid o-5Uy-NHZ H 1:H2-l:H(-l:Hz~-t13-U-phenyl m-ammo (HO-phenyl))-carboxylic acid o-5U2-NHZ H C;Hy-l;H(-1x12-tsn-u-phenyl m- z ammo (HO-phenyl))-carboxylic acid o-SUz NHz H t;Hz-1:H(-l:HZ-rnenyl-ammo m- z cardoxync (HO-phenyl))-acid O-SVz-NHz H C:HZ-liH(-l:Hz_-p y -ammo m- y eri (HO-phenyl))-carboxylic acid o-SUZ-NHZ H C:riz-l;ri(-1:H2-r-phenyl-ammo m- z (HO-phenyl))-carboxylic acid o-~Uz-NHz H c:H2l:H(-c:Hz-l:rt3-phenyl-ammo m-1:(=l.r)wriz (HO-phenyl))-carboxylic acid O-JUz-NHZ H C:HZ-l:H(-l:Hz1;ri3-U-phenyl-ammo m-l:(=V)lVriz (HO-phenyl))-carboxylic acid o-JUz-NHz H l:Hz-1;H(-l:rlztsn-u-phenyl-ammo m-1:(=v)lvriz (HO-phenyl))-carboxylic acid o-SOz-NHz H CHz-CH(-CHz-Methyl m- z phenoxy-acetic (HO-phenyl))-acid ester o-SOz-NHz H CHz-CH(-CHz-Methyl m-C(=NH)NHz Cl-phenoxyacehc (HO-phenyl))-acid ester o- z- z H CHz-CH(-CHz-Methyl m- z F-phenoxy-acetic (HO-phenyl))-acid ester O-5U2 NHZ H C:riz-l:ri(-1:ri2-rnemyl m- z l:Hj-pnenoxy-(HO-phenyl))-acetic acid ester o-5uz-NHz H LHz-l;ti(-l:HZ-a m- z y -p enoxy-(HO-phenyl))-acetic acid ester O-JVZ-NHZ H C:Hz l;ri(-l:Hy-MeLllyl m- y tin-U-prienOXy (HO-phenyl))-acetic acid ester o-SOz-NHz H CHz-CH(-C;Hz-Methyl m- z Yhenoxyacehc (HO-phenyl))-acid ester o- OZ-NHZ H CHz-CH(-CHz-Methyl m- z Cl-phenoxyacehc (HO-phenyl))-acid ester o-SOz-NH2 H CHz-CH(-CHz-Methyl m-C(=U)NHz l~'-phenoxyacehc (HO-phenyl))-acid ester o-JUZ-NHZ t1 I:HZ-l;H(-1:H2-MeTClyll:rig-prieriOXy- m-L(=V)lvri2 (HO-phenyl))-acetic acid ester O-JUy-NHZ H l:HZ l.H(-1:H2-1\nemyl m-1:(=u)lvriz l:ri3-v-pnenoxy (HO-phenyl))-acetic acid ester o- - - ~ a y n_ _p enoxy m=C(~jNHz VV 111 11 v11 ~r11~-v111Y1 Lll 117 V
(HO-phenyl))-acetic acid ester o-5Vz-NHz H C:Hz-C:H(-C;Hz-Yhenoxyacehc m-C:(=NH)NHz acid (HO-phenyl))-o-SUz-NHz H C;Hz-(:H(-C;Hz-C;1-phenoxy-acericm- z acid (HO-phenyl))-o-SOz-NHz z- r -p enoxy- aceticm- z aci (HO-phenyl))-o-SOz-NHz H C:Hz-C;H(-CHz-C;H3-phenoxy-aceticm-(:(=NH)NHz acid (HO-phenyl))-o-SOz-NHz H (:Hz-C;H(-C;Hz-j- -p enoxy-aceticm- z (HO-phenyl))-acid o- z- z z- z- n- -p enoxy aceticm- z aci (HO-phenyl))-o-SOZ NHz H (:HZ (:H(-C:Hz-Yhenoxyacehc m-C;(=U)NHz acid (HO-phenyl))-o-SUz-NHz H C:Hz-C;H(-LHz-C;1-phenoxyacehcm-C;(=U)NHz acid (HO-phenyl))-o-SUz-NHz H C;Hz-(:H(-(:Hz-r~-phenoxyaceticm-C:(=U)NHz acid (HO-phenyl))-o-SOZ NHz H C;Hz-(:H(-C:Hz-(:H3-phenoxy-aceticm-(:(=U)NHz acid (HO-phenyl))-o-SOz-NHz H (:Hz-(:H(-C;Hz-C:H3 U=phenoxy m-(:(=U)NHz acetic (HO-phenyl))-acid o- z- z r z- n- -p enoxy aceticm- z aci (HO-phenyl))-O-JVZ-NHz tl lal2-fall-l,tlZ-YnenOXyeLIlan01 m-l,l=ivtlJlVtlz (HO-phenyl))-o-~uz NHz H l:Hz-l:til-~aiz-1:1-pnenoxy-emanoim-l:l=ivttlivtiz (HO-phenyl))-o-JVZ-NHZ t1 ;rizW;til-l~ti2-t'-prienOXy- m-eTtlanoi (HO-phenyl))-o-5Vz NHz r r 3-p enoxy-a ano m- z (HO-phenyl))-o-~uz-NHz z- z- 3 -p enoxy-a m- z ano (HO-phenyl))-O-JVz-Nriz H l:Hz l:Hl-l:riz-tsn-u-pnenoxy m-l:l=ivryivtiz emanoi (HO-phenyl))-o-~uz-mtiz ti z- z- enoxye ano m- z (HO-phenyl))-O-JVZ-Nriz z- z- -p enoxye ano m- z (HO-phenyl))-O-JV2 NHZ H Cain-l:H(-1;H2-r-pnenoxy-emanoim-l:l=uJivriz (HO-phenyl))-o-~uz-mtiz ti lain lail-laiz-lai3-pnenoxy-emanoim-l;l=~~ivriz (HO-phenyl))-o-~uz-NHz H ~riz-~ril-~riz-~n3-~-Pnenoxy- m- z emanoi (HO-phenyl))-O-JUZ-NHz H l;Hz-Gail-Cain-tin-V-pneriOXy- m-l:l=u)iVtlz elllanoi (HO-phenyl))-o-auz-NHz H laiz-l:ril-~riz-iviemyi pnenoxy-emyim-l;l=mri~wriz (HO-phenyl))-ether o-~uz-Ntiz ti laiz-l,til-l:riz-iviemyi la-pnenoxyetnyim-l:l=ivryivriz (HO-phenyl))-ether o-~uz Ntiz ti ~riz-~-nl-~riz-iviemyi r-pnenoxy-ecnyim-l:l=ivri~wry (HO-phenyl))-ether o-~uz NHz H LHz-l,ril-l:riz-iviemyi pry-pnenoxy-m-l:l=ivryvriz (HO-phenyl))-ethyl ether O-JUz-lVri2 t1 1x12-fail-Cal2-nnemyi ~i-y-u-pnenoxy-m-l:l=ivriyvriz (HO-phenyl))-ethyl ether O-JVZ NHy H 1.H2-lail-l;riZ-Meinyi ISn-u-pnenOXym-(HO-phenyl))-ethyl ether o-z- z z- z- et m- z y enoxye y (HO-phenyl))-ether o-JVz-Nriz t~ ~riz-Ltil-~riz-Merry m- z Li-pnenoxyemyi (HO-phenyl))-ether O-JVz-NHz t~ ~riz-~ti(-c:riz-Merry m- z r-pnenoxyemyi (HO-phenyl))-ether o-5Uz-Ntlz H 1;t12-l;H(-l;tlz-Mettlyl m- z C;ri3-(HO-phenyl))- phenoxyethyl ether o-5u2 tiz ri c:tiz ~t1(-~tlz- Metnyi Lti3-u- m-~~=u~Nriz N
(HO-phenyl))- phenoxyethyl ether o-5Vz tiz ti lalz l;H(-l;tlz- Melllyl tSn-u- m- z N
(HO-phenyl))-phenoxyethyl ether o-5Vz-Ntlz t1 z- z- p m- z eny (Cl-phenyl))-O-JVZ tlz ti Calz-lal(-lalz-l;l-pnenyl m-l:(=lVt1)lVtlz N
(Cl-phenyl))-O-5Vz-Ntiz ti 1:112-lat(-laiz-r-prienyl m-(Cl-phenyl))-o-5uz-Ntiz ti c:riz-l:ri(-l,riz-~;tt3-pnenyi m- z (Cl-phenyl))-o-5uz t-iz tm :riz-pry-~riz~rij-u-pnenyi m- z N
(Cl-phenyl))-O-5Vz-Ntlz ti l;tlz-lal(-l;tiz-t5n-V-prienyl m- z (Cl-phenyl))-o-JUz-Nriz ti laiz-l:ri(-l.:riz-p m- z eny (Cl-phenyl))-o-JUZ-Nriz ti laiz-Lti(-l,tiz_-p m- z eny (Cl-phenyl))-O-SUz-Nriz ti c;tiz c:ri~-~riz-r-pnenyi m-~~=u~wriz (Cl-phenyl))-O-JVZ t12 H 1;t12-lal(-l:riy-~ri3-pnenyi m- z N
(Cl-phenyl))-o-~uz-Ntlz ti ~alz-Lt1(-Lrlz~;tlj-urpnenyi m- z (Cl-phenyl))-O-JU2-Ntiz n ~riz-pry-~riznn-u-pnenyi m- z (Cl-phenyl))-o-au2 riz ri l:riz-l:ri(-l:riz-Amime p- z N
(Cl-phenyl))-o-JUz-Nriz ti laiz-la1(-latz--am p- z 1ne (Cl-phenyl))-o-SVZ tiz z z- -am p- z N me (Cl-phenyl))-o-JVz-Nri2 ti l:riz lay(-~;t~z-~at3-am~me p-~:~=Nti~ruriz (Cl-phenyl))-O-JVz-Nriz ri c:riz-lairc:riz-3- p- z -am me (Cl-phenyl))-O-JUz-Nri2 n z- z n- p- z -ant me (Cl-phenyl))-o-z z z- z- m p- z me (Cl-phenyl))-o-~uz-Nrtz ti c:nz t_;ty-~riz-m-amime p-~~=u~~riz (Cl-phenyl))-O-JVZ-Ntiz ti 1x12-litl(-lalz-r-amlllle p-L(=V)lVriz (Cl-phenyl))-o-~uz-Nriz m :riz-pry-~tiz-~ri3-amnne p-~~=u~r~riz (Cl-phenyl))-O-JVZ riz m :riz-~ri~-~riz-~ri3-u-amime p-~~=u~r~riz N
(Cl-phenyl))-o-~uz-Ntiz rm :riz-pry-~riz-nn-v-amime p-~~=u~mriz .
(Cl-phenyl))-O-JVz-Nriz rm ;riz-pry-~riz-rnenyi-ammo-carooxyiic m- z (Cl-phenyl))-acid o- z z z- z- eny -ammo m- (=NH)NHz w.m a a v (C1-phenyl))-carboxylic acid o-5uz-NHz H c:Hz-l:Hl-t;Hz-r-pnenyi-ammo m-~:(=mry~riz (Cl-phenyl))-carboxylic acid o-SUz NHz H c.;Hz-t;H(-l:Hz-c:H3-pnenyi-armnom-l:l=NtyNriz (Cl-phenyl))-carboxylic acid o-JVz-NHz H ~riz-~Hy:Hz1:H3-u-pnenyi m-l:l=~ryr~ry ammo (Cl-phenyl))-carboxylic acid O-JV2-NHz H l:riz-l:ril-c:Hz-nn-v-pnenyi ammom-~(=~ryr~riz (Cl-phenyl))-carboxylic acid o-5uz NHz H l:Hz-l:Hl-c:Hz-rneny-ammo carnoxyncm-l:l=v~Nri2 (Cl-phenyl))-acid o-JV2-NHz H l:Hz-l:Hl-laiz-la-pnenyi-ammo m- z (CI-phenyl))-carboxylic acid o-~uz NHz H l:Hz-t;Hl-c:riz-r-pnenyi-ammo m-l:l=~Jmriz (Cl-phenyl))-carboxylic acid o-~uz NHz H l:riz-l:ril-l:riz-~ri3 pneny-ammo m-~(=lywriz (Cl-phenyl))-carboxylic acid O-JUZ-NHz H l:riz-l:ril-l:riz-~ri3-v-pnenyi-ammom-~(=v~~riz (Cl-phenyl))-carboxylic acid o-SUZ NHz H l:Hz-c:Hl-l:Hz-tsn-u-pnenyi-ammom- z (Cl-phenyl))-carboxylic acid o- Z z H CHZ CH(-CHz-Methyl phenoxy-aceticm- z (Cl-phenyl))-acid ester o- z- z - H CHz CH(-CHz-a y -p enoxyacehcm- z (Cl-phenyl))-acid ester o- z- z H CHz CH(-CHz-a y -p epoxy- m- z acetic (Cl-phenyl))-acid ester o-JVZ NHz H 1;H2-l:ril-1:ri2-metnyi lai3-pnenoxy-m- z (Cl-phenyl))-acetic acid ester o-5uz-NHz H 1:HZ l:Hl-l:Hz-Metnyi l:ri3 m- z u-pnenoxy-(Cl-phenyl))-acetic acid ester o-5U~ NHz H ~:Hz-c:Hl-c:H2-Metnyi tsn-u-pnenoxym- z (Cl-phenyl))-acetic acid ester o-SOz-IVHz H CHz-CH(-CHz-Methyl Yhenoxyacehcm- z (Cl-phenyl))-acid ester o- z- z H CHz-CH(-CHz-Methyl Cl-phenoxyacericm- z (Cl-phenyl))-acid ester o- Oz-NHz H CHz-CH(-CHz-Methyl r~-phenoxyacehcm- z (Cl-phenyl))-acid ester O-JUZ-Nriz H l:Hz-lail-l:riz-Memyi lai3-pnenoxy-m- z (Cl-phenyl))-aceric acid ester O-5Uz-NHi H l:Hz C.:HI-1;H2-lVlemy11x13 u-pnenOXym-(Cl-phenyl))-acetic acid ester o-5uz-NHz H c:Hz-l:Hl-LHZ-Metnyi tsn-u-pnenoxym- z (Cl-phenyl))-acetic acid ester o-SOz-NHz H z- z- enoxyacehc aci m- z (Cl-phenyl))-o- Oz-NHz H CHz-CH(-CHZCl-phenoxy-aceticm-C(=NH)NHz acid (Cl-phenyl))-o-SOz-NHz H CHz-CH(-CHz-F-phenoxy- aceticm- z acid (Cl-phenyl))-o- Oz-NHz H CHz-CH(-CHz-CH3-phenoxy-aceticm- z acid (Cl-phenyl))-o-SOz-NHz H r r s- -p epoxy-aceticm- z (Cl-phenyl))-acid o-SUz-NHz H CHZ CH(-CHz-tan-U-phenoxy m-C(=NH)NHz acetic acid (CI-phenyl))-o-SOz-NHz H CHz-CH(-CHz-Yhenoxyacehc m-C(=U)NHz acid (Cl-phenyl))-o-SOz-NHz H CHz-CH(-CHz-Cl-phenoxyacehc m-C(=U)NHz acid (Cl-phenyl))--o- z- z r r -p enoxyacehc .., ...,...
acl m- z (Cl-phenyl))-o- z- z z- z- ,-p enoxy-aceticm-C(=O)NHZ
acl (Cl-phenyl))-- - z ~ CHz-~z -- ~~_O=p~noxy aceticm-C(=U)NHz (Cl-phenyl))-acid o- z- z H CHz-CH(-CHz-n- -p enoxy aceticm- z acl (Cl-phenyl))-o-SUz-NHz H z- - z- enoxye ano m- z (Cl-phenyl))-o-5Uz NHz H ~%HrLHI-Lriz-Ll-pnenoxy-emanolm- z (Cl-phenyl))-o-SU2 NHz H ~;HZ-c:Hl-~:Hz-r-pnenoxy- emanolm- z (Cl-phenyl))-O-SUy-NHy H 1:r12-(:Hl-1:H21;H3-prienoxY-elllariolm-(Cl-phenyl))-O-JUz-NHZ H lalZ-l;tll-l:riz-~ri3-V-pnenoxy-emanolm-~:l=mri)~riz (Cl-phenyl))-o-5Uz-NHz H LHz-LHl-LHz-~n-u-pnenoxy m- z emanol (Cl-phenyl))-o-5Uz-NHz H c:Hz-uHl-LHZrnenoxyemanol m-~l=v)wriz (Cl-phenyl))-o-JUZ-Nri2 H Lriz-Lnl-Lnr~l-pnenoxyemanoim- z (Cl-phenyl))-O-5u2-NHZ H 1:H2-l;Hl-l;Hzr-prienoxY-ethanolm-(Cl-phenyl))-o-5Uz-Nriz H z- z- 3-p enoxy-a ano m- z (Cl-phenyl))-o-5Uz-NHz H z- z- 3- -p enoxy- m- z a ano (Cl-phenyl))-o-5Vz-NHz H Lriz-LHl-LHztsn-u-pnenoxy- m-~;l=u)lrrlz ethanol (Cl-phenyl))-o-5U2 NHz H LHz-LHl-calz-a Y p enoxy-a m- z y (Cl-phenyl))=ether o-SUz-NHz H (:Hz-C:HI-c:Hz-a y -p enoxye m- z y (Cl-phenyl))-ether o-SUz NHZ H (:HZ-LHl-c:H2-a y -p enoxy-a m- z y (Cl-phenyl))-ether o-SUZ-Nriz H LHz-LHl-c:Hz-lvieulyl ~H3-pnenoxy-m- z (Cl-phenyl))-ethyl ether o-5uz-NHz t1 :Hz-t;Hl-Ltiz-lvietnyl ~tlj-u-pnenoxy-m-~l=lrri)lrrlz (Cl-phenyl))-ethyl ether o-~Uz-NHz ti uHz-c:ry-~rlz-lvietnyl nn-v-pnenoxym- z (Cl-phenyl))-ethyl ether o-JVz-NHz ti MHz-~tll-~lnz-mlemyl rnenoxyemylm-~l=u)mriz (Cl-phenyl))-ether o-SOz-NHz H CHz CH(-CHz-Methyl Cl-phenoxyethylm- z (Cl-phenyl))-ether o-~u2-NHz H (aiz-~:Hl-Ltiz-lvlemyl r-pnenoxyetnylm- z (Cl-phenyl))-ether o-JVZ-NHZ H (a12-l;Hl-1;H2-MeLllYll;ri3- m-l;l=u)lVrlz (Cl-phenyl))-phenoxyethyl ether o-JVZ NH2 H 1;H2-fall-l;tlz-MeTllYl 1x13-v- m-(Cl-phenyl))-phenoxyethyl ether o-~uz-NHz H ~tlz-c:rll-c:riz-a y n- m- z (Cl-phenyl))=phenoxyethyl ether o-~u2-Ntlz ti MHz-~rll-c:riz-p eny m- z ~2)-o-JUz-NriZ tm :H~ Ltll-caiz_-p eny m- z ~z)-o-~uz-Ntlz z z- -p eny m- z ~z)-o- r z . z- 3-p eny _ m-z ~
~-z o- z- z z- z- s- -p eny m- z ~z)-o- z- z CHz-CH(- n_ _p eny m_C(_~~z z ~z)-O-JUZ-NHZ H 1:H2-l=H(-l;HZ-pnenyl m-~z)-O-JUZ-NHZ H 1:H2-l:H(-1:H2-l:l-prieriyl m-NHz)_ o-JUZ-NHZ Z- Z- -p eny m- z NHz)_ -o- z- z z_ z_ 3-p eny m-C(-O~Z
~z)-O-~Uz-NHz z- z' 3- -p eny m- z NHz)_ o- z- z z- z- n- -p eny m- =O
~z)-o-JUZ-NHZ H l:Hz-l:H(-1;H2nl me p-NHz)_ O-JVZ-NHZ H l:Hz-l:H(-l;HZ-l:l-anllme p-~z)- , o-JVz-NHZ H 1,H2-l:H(-l.HZ-r-anllme p-L(=1VH)lVriz ~2)-O-JVZ NHZ H 1:H2-l.;H(-1:H2-1.H3 amlllle p-l:(=1VH)lVHy ~z)-O-JUZ-NHZ H liHZ-l;H(-l:Hz1;H3 V-anlllrie p-NHz)-O-1U2-NHZ H l:HZ-lJH(-l:HZlin-V-amllIie p-NHz)_ o-~Uz-NH2 H 2- z llie p-~z)-O-JVZ-NH2 H 2- 2- -and me p-~z)-o-5Uz-NHZ H Z_ z_ -and me p-~2)-O-JUZ-NHZ Y z' 3 am 1ne p-~z)-o- z z r z- 3 -am me _ p_C(_O)NHz NHz)_ O-JUZ-NHZ Y z- n- -and me p- z ~z)-o-5Uz-NHz i r eny -amino-car m- z oxy lc NHz)- acid - -o- z- z z- z- eny -ammo m_~~ ~NHz v1 1 11 1 NHz)- carboxylic acid o- r a r z- -p eny -amino m_ y 1.111.11 NHz)- carboxylic acid o- z z z- z' 3 p enyl-amino--m-C(=NH)NHz -v11 11 NHz)- carboxylic acid o- z- z z- r m-C(=NH)NHZ
trll V
s- -pheny amino NHz)- carboxylic acid o- z- z z- z- n- -p eny amino m- z NHz)- carboxylic acid O-JV2-NHZ H l:HZ-l:H(-l.;HZ-Ynenyl-amlllo m-l;(=ll)1VH2 CarOOXyIIC
NHz)- acid o-~uz-NHz H ~;Hz t.HIw:HZw:I-pnenyl-ammo m- z NHz)- carboxylic acid O-JVZ NHz H l:HZ l:H(-1:H2-r-pnenyl-arillnom-l:(=V)lVHz NHz)- carboxylic acid O-JVZ NHz H 1:H2 l:H(-1~t12-1x13-pneriyl-ammom-l=(=U)lVHz NHz)- carboxylic acid z c m z uo l NH2)- ic a d carboxy o- z- z z- z- n- -p eny -aminom-C(=O)NHz 17 t. ..
NHz)- carboxylic acid ~
o- z- z z- a y p enoxy-aceticm- z r NHz)- acid ester o- z- z z- r a Y -p enoxyaaehcrn-C(=~N)=IZ
NHz)- acid ester o- z- z I~ CHz-CH(-CHz-Methyl F-phenoxy-m- z acetic NHz)- acid ester o-5Vz Ntl2 H 1;ri2-lal(-l;ti2-Memyi l:rt3-pnenoxy-m- z NHz)- acetic acid ester o-~Uz lvrtz H laiz-cay-c.;tiz-a Y r -p enoxy- m- z NHz)- acetic acid ester o-~Vz-Ntlz ti (:rtz-Lti(-l:rlz-a y n_ -p enoxy m- z NHz)- acetic acid ester o- 2 z - H CHz CH(-CHz-a y enoxyacehc m- z NHz)- acid ester H z- r a y -p enoxyacehcm- z o- i z NHz)- acid ester o- z- z z- z- m-C(=O)NHz ...
erioXyacetic NHz)- acid ester o- z- z z- z- m-C(=O)NHz m ua m.m a a Y 3-p enoxy-NHz)- acetic acid ester o- z- z z- z- m-C(=O)NHz m ua m.ai v as a Y s- -p enoxy NHz)- acetic acid ester o- z- z r z- a y n- -p enoxy m- z NHz)- acetic acid ester o- z- z z z- enoxyacehc acid m-C(=NH)NHZ
~z)-o- Z 2 H CHz-CH(-CHz-C1-phenoxy-aceticm- z acid ~2)-o-S02-NHz H CHZ CH(-CHz-F-phenoxy- aceticm- z acid o-SO~ NHZ H CHz-CH(-CHz-CH3 phenoxy-aceticm-acid ~z)-o- 2 z H CHz-CH(-CHz-3- -p enoxy-aceticm- z NHz)- acid o- z- z H CHz-CH(-CHz-n- -p enoxy aceticm- z aci ~z)-o- Z-NHz H CHz-CH(-CHz-Yhenoxyacehc m- z acid ~z)-o- z-~z ~ z- z- -p enoxyacehc m- z aci NHz)_ o- z-NHz H z- z- -p enoxyacehc m- z aci NHz)-o- z- z z- z- 3-p enoxy-aceticm- z aci ~z)-o- z- z z- z- 3- -p enoxy aceticm- z NHz)- acid o- r z H z- r n- -p enoxy aceticm- z aci ~2)-o-JVz lVtiz r1 Lriz-Lril-1-nrenoxye ano m- z ~z)-o-wz-Nriz ti ~riz-~ry-~riz-la-pnenoxy-emanoim- z ~z)-O-JVz-Nriz ti laiz-qty-laiz-r-pnenoxy- etnanoim-~~=r~ry~riz ~2)-O-JUy-1Vt12 n l.tlz l.Yl~-1,ri2-1.113 pnenoxy-emanoim-~~=mry~ri2 NHz)_ o-auz-Nriz tm :riz-l:ry-l:rizl:ri3-V-pnenoxy-emanoim-1:~=~ry~riz ~z)-o-z- z z- z- n--p v~ ..~~y..
epoxy m-a ano NH2)_ -2- 2 2- z' enoxye m-C(=O)NHz ano a as ua a ~2) o-z- z z- z- m-C(~jNHz v..a as ua a -p enoxye ano ~2) o-z- z z- z- -p m-C(=O~NHz epoxy-a ano a' as ua a ~2)-o-z z z- z- 3-p m-C(=O)NHz epoxy-ethanol NHz)_ O-SUz-NHZ H l:Hy-l:Hl-l:Hz1:H3-V-pherioxy- m-ethanol ~2)-o-~Vz-NHz H MHz-LHl-LHz-tsn-V-pnenoxy- m- z ethanol ~z)-O-JUy-NHZ H l:HZ-l:Hl-l:HZMethyl m-pnenOXy-eLllyl NHz)- ether o-JUz Hz H ~alz-LHl-trHZ-lmemym;l-pnenoxyeulyl m-t.l=lvrylrriz 1v NHz)- ether O-5UZ-NH2 H C:HZ-C:HI-I:HZ-lVleUlyl m-l;l=1VH)1VH2 r-pheriOXy-emyl lVHz)- ether o-JVz-NHZ H 1;H2-(:Hl-l;Hz-Melllyll:H3-prienOXy- m-NHz)- ethyl ether O-JUz-NH2 H LHZ-LHl-~atz-a m- z Y
s--P
epoxy-NHz)- ethyl ether o-SVz-NHz H ~:Hz-c:Hl-t,Hz-a m- z y n_ -p epoxy NHz)- ethyl ether o-SUz-NHz H ~;Hz -t,HZ-a m- z Lttl y enoxye y NHz)- ether O-JVZ-NHz H I;HZ -l.;HZ-a m- y call y -p eriOXye y NHz)- ether o-~UZ Hz H 1:H2-l:Hl-l.;HZ-Memyl m- y N r-pneriOXyemyl NHz)- ether o-JVZ-NHZ H 1;t12-l:Hl-1:H2-a m- z Y
s-NHz)- phenoxyethyl ether o-JVZ-NHZ H 1:H2-l:Hl-l:Hz-i Vlemyll:rlg-v- m-NHz)- phenoxyethyl ether o-JUz-NHz H ~;Hz-fall-LHZ-t vlemyl m-~l=m~lvriz tsn-v-NHz)- phenoxyethyl ether o-z- z s z P m- z ehY
o-z- 2 3 2 -P m-C(-~)~z ehY
o-r z s z -P m-~;l=lvtl~lvti2 enY
o-z- 2 3 2 9-P m- z enY
o-z- 2 3 2 3- p eny m-~l=lvrl~lvriz -o-z- z s z n_ eny m- z _p o-z- z s z P m-t,l=U)lvti2 ehY
o-2 2 3 2 -P m- z enY
o-z- z s z -P m- z enY
o-z- 2 3 2 3-p m- =O)~2 eny o-z- z a z 3- p eny m- z -r z s z n_ eny m-_p o-z- z s z me P- )~z o-r z s z -am p-C(=NH)NHz me o-z- z s z -and p- z me o-z- z s z 3-am p- z me o-z- z 3 z 3- p- z -and me o-z- z a z n- p-C(=NH)NHz _~
me o-z- z s z m p- z me o-z- z s z -am p_ me O-z- z s z -aIll p- 2 1ne o-z- z s z 3-3niI-me p- NHz o-z- z s z 3- p- z -am me o- z- z 3 z n_ p~(_O)~z _am me o- z- z ~ z eny m-C(=NH) -ammo-carboxylic z acid o-JUz-NHz 3 z eny m- z -ammo carboxylic acid o-JUZ-NHZ 1x13 1.;H2 r-pnenyl-amlllo m-l:(=NH)NH2 carboxylic acid o-~Vz-NHz LH3 MHz ~H3-pnenyi-ammo m-~(=Nri)Nriz carboxylic acid o-JUz-NHy 1:H3 1;H2 1x13-u-pnenyl m-l;(=NH)NHZ
amlIlO
carboxylic acid O-JUy-NHz c:H3 ~:Hz rsn-u-pnenyi m- z ammo carboxylic acid O-JV2-Nriz c:H3 ~:Hz rnenyi-ammo m-~;~=u)ivtiz carooxync acid O-JUZ-NHZ ~H3 ~tiz m-pnenyi-ammo m-~~=~)Nriz CH3carboxylic acid o-auz NHz uH3 ~:HZ r-pnenyi-ammo m-~t=~)wriz carboxylic acid O-~Vz-NHz ~H3 uHZ ~H3-pnenyi-ammo m-~~=v)Nriz carboxylic acid O-lUZ-NH2 l:Hg l;HZ 1;H3-u-pnenyl-am111o m-carboxylic acid o- z- z s z n- m-C(=O)NHz -phew=ammo -carboxylic acid o- z- z CH3 CHz Methyl m- z phenoxy-acetic acid ester o- Oz-NHz CH3 CHz Methyl m- z C1-phenoxyacehc acid ester o- z- z CH3 CHz Methyl m- z F-phenoxy-acetic acid ester o-5V2-Nriz c:H3 ~:Hz Memyi m- z pnenoxy-acetic acid ester o- z- z s z a m- z y -p enoxy-acetic acid ester o-5Uz-Nriz LH3 LHz Memyi m-~~=Nri)Nriz tsn-u-pnenoxy acetic acid ester -o- z z s z a m=C(=O)NHz y enoxyacetic acid ester o- z z CH3 CHz Methyl m-C(=U)NHz C1-phenoxyaceric acid ester o- r z ~s CHz Methyl m- z F-phenoxyacehc acid ester o-5Vz-NHz (:H3 c~Hz a m- z y 3-p enoxy-acetic acid ester o-SVZ NHz LH3 ~:Hz Memyi m- z ~H3-u-pnenoxy acetic acid ester O-SUZ-NH2 c:H3 ~:Hz a m- z y n--p enoxy acetic acid ester o- z- z a z enoxyacehc m- z aci o- r z s z -p m-C:(=NH)NHz enoxy-acetic aci o- z- z 3 z -p m- z enoxy-acetic aci o- z- z ~ z 3- p enoxy-acericm- NHz aci o- 2 2 3 2 3 m-(:(=NH)NHz -p enoxy-acetic acid o- z- z s z n- m- z -p enoxy.aceric aci o- z- z s z enoxyacehc m- )NHz aci o- z- z s z -p m- NHZ
enoxyacehc aci o- z- z 3 z -p m- z enoxyacehc aci o- z- 2 3 z g- p epoxy-aceticm- NHz aci o- r 2 3 2 3- -p epoxy aceticm- )NHz aci -o-z- z 3 z n- m- NH2 -p ienoxy acehc aci o-z- z 3 z enoxye m-C(=NH)N
ano z -o-z- z s z -p m-C(= z epoxy-a ano o-r z s z -p m- z epoxy-a ano c-z- z s z 3- p m~NH) z epoxy-a and o-z- 2 3 2 3- - p epoxy-a m- Hz ano n-r z s z n- epoxy a m-C(= z -p ano o-z- z s z enoxye m- z ano o-z- z a z -p m- NHZ
enoxye ano o-z- z s z -p m-C(=O)NHz epoxy-a ano z- z 3 z ,-p m- z epoxy-a ano 2 2 3 2 3' p epoxy- m- z - a ano o-z- z s z n- epoxy- a m- NHz -p ano o-z- z s z a m=C(=N~NHz Y
P
epoxy-a y ether o-~uZ Hz UH3 Uriz nnemyi m-~~=~rywriz 1v m-pnenoxyemyi ether o-JUz-iVriz l:Hj 1:H2 lVleLriyl m-l.;(=1VH)1VH2 r=pneriOXy-e2llyl ether o-SUz Hz c:H3 LHz enemy m- z 1v LH3-pnenoxy-ethyl ether z- z 3 z a m- z y -p epoxy-ethyl ether o-5Uz-iVHz 1:H3 ~:Hz Metnyt m-~:(=lrri)~riz tsn-u-pnenoxy ethyl ether o-JUZ-NHZ 1;H3 lai2 a m-y enoxye y ether o-5Uz-NHz c:Hj ~:Hz a m- z y -p enoxye y ether o-5Uz-NHz c:H3 LHz Memyi m- z r-pnenoxyemyi ether o-5Uz-NHz C.;H3 (:Hz a m- z y phenoxyethyl ether o-5Uz-NHZ C:Hj l:Hi MeTtlyll;H3-U- m-phenoxyethyl ether o-5Uz-NHz C;H3 c:Hz lvlernyl m- z tsn-u-phenoxyethyl ether o-z- z s z- z P m- z enY
o-z z 3 z- z -P m- z enY
o-z- z 3 i z -P m-C(=~)~z enY
z- z 3 z- 2 3- P m- z enY
o-z z 3 z- z 3- - p eny m- NHz o-z- z s z- z n_ eny m=C~ ~)~z -p o-z- z 3 z- z P m- ~z enY
c-z- 2 3 2- z -P m- ~z enY
o-2 2 3 2- z -P m- z enY
o-z- z s z- z 3 p m-eny z- z 3 z- z 3- - p eny m- NHz o-z- z 3 z- z n_ eny m-~~=v~r~riz _p o-z- z 3 z- z m p- z me r z 3 z- z -am p- (=~)~z me z- 2 3 2- z -am p- z me o-z- 2 3 2- z 3-am p- )NHZ
me c-r z s z- z 3- p-t,~=r~ry~riz -am me o-z- z s z- z n_ p- z _anl me a-z- 2 l 2- z me P- NHz o-r z s z- z -am p-me o-z- z s z z -am p- z me -o-z- 2 3 2- z 3-am p- Hz me -o-z- z s z- z 3- p- (=O)NHz -am me o_z_ z CH3 z- z n- P- z -am me o-z- z CHj z- z eny m-C = z -ammo-car oxylic acid o-SUz-NHz 3 (:Hz-(:Hz C1-Phenyl-arrimo m-C:(=NH)NHz carboxylic acid o-~uz-ivtiz ~rij ~riz-~riz r-pnenyi-ammo m-~t=r~ryNriz carboxylic acid o-JUz-NHz l;rlj lalz-lalz Cal3-pnenyl-amlrio m- z carboxylic acid o-~uz-NHz ~n3 r z 3- m- z -p eny ammo carboxylic acid O-JUz-Nriz 3 z- z n- m- z -p eny ammo carboxylic acid o-~uz-lvriz ins ~riz-~riz rnenyi-ammo m- z carooxync acid o-JVz-Nri2 1x13 ~;tlzWa1z t_;1-pnenyi-ammo m- z carboxylic acid O-JUz-NHz Lti3 ~aiz-Ltiz r-pnenyi-amino m-~:~=v)~riz carboxylic acid o-~Vz-Nriz caij ~:riz-Ltiz ~ai3-pnenyi-ammo m- z carboxylic acid o-5Uz-Nriz cai3 ~aiz y ai3-u-pnenyi-ammo m-~:(=uJr~tiz ca carboxylic acid O-JVz-NHz Lti3 Ltiz aiz nn-u-pnenyi-ammo m-~~=v~~riz c carboxylic acid o-z- z 3 z- z a m- z y p epoxy-acetic acid ester o-z- z CH3 CHz-CHz Methyl m-C(=NH)NHz C1-phenoxyacetic acid ester o-SOZ-NHz CH3 CHz-CHz Methyl m- z 1'-phenoxy-acetic acid ester o-z- 2 3 2- z a m- z Y
a-P
epoxy-acetic acid ester o-JVz-Nriz Lti3 Ltiz riz a m- z ~ y ,--p epoxy-acetic acid ester O-JVi Hz LH3 c:riz-~ttz Memyi m- z N nn-u-pnenoxy acetic acid ester o-z- z - CH3 CHz Hz Methyl m-C:(=V)NHz C Yhenoxyacehc acid ester o-z- z CH3 CHZ Hz a m- z C y -p enoxyaceric acid ester o-z- z Hs r z a m- z y -p enoxyacehc acid ester o-SVz-NHz C.H3 t;tiz-t;riz nnemymai3-pnenoxy- m- z acetic acid ester o-5Uz-NHz c,tij ~:riz-~aiz nnemymai3-v-pnenoxy m- z acetic acid ester o-SVz-Nriz t.ri~ c:riz-~;tiz Memyi m- z tsn-v-pnenoxy acetic acid ester o-z- 2 3 2- z enoxyacehc m- z act o-z- 2 3 2- z -p m- NHz epoxy-acetic act o-z z s z z -p m- z epoxy-acetic act Y 2 3 2- z 3- p epoxy-aceticm-C;(=NH)NHz act o-z- z s z- z 3- m- z -p epoxy-acetic acid o-z- z s z- z n- m- z -p epoxy acetic act o-r z s r z enoxyacehc m-C(=U)NHz act o-z- 2 3 2 2 -p m- z enoxyacehc act o-z- z s z- z -p m- z enoxyacehc act o-z- z s z- z 3-p m- z epoxy-acetic act o-z- 2 3 2- z 3- m- )NHZ
-p epoxy acetic aci o-z- z a r z n- m- z -p -enoxy acehc aci -o-r z 3 z- z enoxye m-C(=NH)NHz anol z- 2 3 2- z -p m- z enoxy-a ano --o-z- z a z- z -p rn-C(--NHjN>
enoxy-a anol -o-z- z s z- z 3-p m=
enoxy-a ano o-r z 3 z- z 3- p enoxy-a m- z - ano o-z- z 3 z- z n_ enoxy a m-~~=wrywriz _p ano o-z- z a z- z enoxye m- z ano -o-z- z 3 z- z -p m-C(=O
enoxye anol o-z- z 3 z- z -p m- z enoxy-a ano o-z- z 3 z- z 3- p m-~~=v~ivtiz enoxy-a ano o-z- z 3 z- z 3- - p enoxy- m- z a ano o-z- z 3 z- z n- enoxy- a m- z -p ano -o-z- z s r z a m-C(=NH)NHz Y
P
enoxy-a y ether o-5U2-Nriz 1:H3 l;Hz Hz lVlemyl m-l; l:1-prienOXyeillyl ether o-5Uz-NHz ~;H3 ~:HZ Hz Memyi m- z L r-pnenoxy-etnyi ether o-5Uz-NHz 1;H3 1;H2-C.HZ Melllyll:H3-pnenOXy- m-l;~=lVt1)lVrlZ
ethyl ether O-5uz-NHz Sri, c:Hz-LHz nnemyi m- z ~ri3-v-pnenoxy-ethyl ether o-5uz-NHz c:H3 ~Hz-~ Hz nnecnyi m- z rsn-v-pnenoxy ethyl ether o-5Uz-NHz c:H3 c:Hz-LHz lvlemyi m- z rnenoxyemyi ether o-5Uz-NHz c:H3 LHZ Hz Memy m- z L m-pnenoxyemy ether o-~u2 Hz c:H3 MHz tiz Memyi m-~~=~yvmz N ~ r-pnenoxyemyi ether O-JUz-NHZ C:H3 C:HZ-1;H2 MeUlyll;rij m-phenoxyethylether o-5Uz-NHZ (:H3 C:HZ-l~Hz Memy1 m-l;(=V)lVrlz C;H3-u-phenoxyethylether O-JVZ-NHZ C.;H3 l;Hz-l:Hz Melllyl m-li(=V)1vt12 tiri-V-phenoxyethyl ether o-z- 2 3 2- r z P m- z enY
o-r z 3 z- z-z -p m-~.~=mnyvtiz eny z- 2 3 2- z-z -p m-eny o-z- z 3 z- z-z 3- P m- z enY
o-z- 2 3 2- z-z 3- - p eny m-C(=1VH)NHz o-z- 2 3 z- z-z n_ eny m_ )NHz _p o-2 2 3 2 2 2 P m- (=a)~z enY
o-r z 3 z- z-z -P m- z enY
o-z- 2 3 2- z-z -p m-L(=V)lvtiz eny 2- 2 3 2- 2 2 3- p m- z eny 2 2 3 2- 2 2 3- - p eny m- z z- 2 3 2- z-z n- eny m- z -p o-z- z 3 z- z-z m p- z me o-z- z 3 z z-z -am p- z me z- 2 3 2- z-z -am p-~~=mnyvriz me o-z- z s z- z-z 3-am p- z me o-z- z 3 z z-z 3 p- NHz -am me o-z- z 3 z- z-z n- p- z -$m me o-z- z s z z-z m p- ~_O)NHz me o-z- z s z- r z -am p- z me o-z- z s z- z-z -am p-~;~=v)lvttz me z- z 3 2- z-z ; p- N
am me z- 2 3 2- z-z 3- P- NH2 -am me o-z- z s z- z-z n- p-~;(=U)ivttz -am me o-z- z ~ 3 z- z-z eny m- z -ammo-car oxy is acid o-JVz-NHz j z- z-z eny m- z -ammo carboxylic acid o-~Vz-NHZ 1x13 LHz-LHz-~-Hz r-pneriyl-ammo m-l:(=Ntt)iVtlZ
carboxylic acid o-JVZ HZ lal3 LHz-LHz-~-HZ ~-Hs-pneriyl-ammo m-N carboxylic acid o-JVZ-NHZ laij 1x12-Caiz-~;tiz 1;t13-V-prienyl m-t:(=Nti)iVtiz ammo carboxylic acid o-auz-Ntiz ~ri3 ~HZ-~HZ-~HZ ~sn-u-pnenyi m-~(=~ri)Nriz ammo carboxylic acid o-JVz-Ntiz Lti3 ~:HZ-LHZ-LHz rnenyi-ammo m-~(=v)Ntiz cardoxyiic acid o-JV2-NH2 C:ri3 l:rizalzri2 l:l-phen yl-amlllo m-l:(=V)Nri2 l 1; carboxyl ic acid O-JUz-NriZ Lti3 ~HZ-~HZ-~HZ r-pnenyi-ammo m-~(=v)mriz carboxylic acid O-JUz-NH2 c:H3 Ltiz-~aiztiz ~;ti3-pnenyi-ammo m- z L carboxylic acid o-JVz-Nriz LH, ~tiz-Ltiztiz ~ti3-u-pnenyi-ammo m-~(=u)Nriz L carboxylic acid o-JU2-Ntlz (a13 ~-HZ-~-HZ-LHz tsn-u-pnenyi-ammo m-~:(=~Jr~riz carboxylic acid o-r z 3 CHz-CH2Hz Methyl m- z C phenoxy-acetic acid ester o-z- z 3 CHz-CHz-CHz a m- z y -p enoxyacehc acid ester o-z- z , CHz-CHz-CHz a m- z y -p epoxy-acetic acid ester o-5Uz-Nriz LH, caiz-~;t12tiz a m- z L y 3-p epoxy-acetic acid ester o-5Vz-NHZ 1;H3 ~-H2-~-riz-~-HZ Meulyl m-~a13-v-pnenoxy-acetic acid ester o-JVz-NHz 1:H3 LHz-Lriz-~-Hz Methyl m- z tsn-u-pnenoxy acetic acid ester o-r z s CHz-CHzHz Methyl m-C(=U)NHz C Yhenoxyacehc acid ester o-SOZ Hz CH3 CHz-CHzHz Methyl m- z N C Cl-phenoxyacetic acid ester o-SOz~lH2 CH3 CHZ HZHz Methyl m-C(=U)NHz C C F-phenoxyacehc acid ester o-~uz-NHz t;H3 c:riz-~tiz-~tiz Memyi m-~(=~)r~riz ~ri3 pnenoxy-acetic acid ester z- 2 3 2- z-z a m- z Y
a--p epoxy acetic acid ester z- 2 3 2- z-z a m- z y n--p epoxy acetic acid ester o-z- z 3 z- z-z enoxyacehc m- z aci o-z- z s z- z-z -p m- (~NHz epoxy-acetic aci o-z- z s z- z-z -p m- z epoxy-acetic aci o-z- z a z- z-z 3- p m-C(=NH)NHz epoxy-acetic aci O-SOz-NHz 3 z z-z 3- m- z -p epoxy-acetic acid o-z- z s r r z n- m- z -p -epoxy acettc aci o-z- z s r z-z enoxyaceric m- NHz aci o-z- 2 3 2- z-z -p m- NHz enoxyacehc aci o-r z ~ r r z -p m- =O)NHZ
enoxyacehc aci o-z- z 3 z- z-z 3 m- N
p epoxy-acetic aci o-z- 2 3 2- z-z 3- m- NHz -p epoxy acetic acl o-z- z 3 z- z-z n- m- Hz -p epoxy acehc acl --o-z- z ~3 z- z-z enoxye m-C(--NH) ano z o-r z 3 r r z -p m- z epoxy-a ano o-z- 2 3 2- z-z -p m- ~~ z epoxy-a ano o-z- z 3 z- z-z 3- p m- z epoxy-a ano o-z- z 3 z- z-z 3- - p epoxy-a m- z ano o-z- 2 3 2- z-z n- epoxy ethannolm-C(=NH)N
-p o-z- 2 3 2- z-z enoxye m- z ano --o-z- z 3 z- z-z -p m~
enoxye ano o-z- z 3 z- z-z -p m- (=O z epoxy-a ano o-z- z 3 z- z-z 3-p m- z epoxy-a -ano o-z- z 3 z z-2 3- p epoxy- m- z - a ano --o-z- z 3 z- z-z n- epoxy- m=C(=O)NHz -p ethanol -o-r z 3 z- z-z a m-C(=NH)NHz Y
P
epoxy-a y ether O-JVz-Ntiz ~ti3 ~riz-~tizriz a m- z ~ y -p enoxye y ether o-~V2 tiz Lti3 ~tiz-~rizaiz nnemyl m-~~=mriJmriz N c r-pnenoxy-emyl ether o-r z s z- z-z a m- z Y
3-p epoxy-ethyl ether O-JVZ-Nt12 Lti, ~riz-~:riz-~riz Memyl m-~~=rrryvriz ~ri3-V-pnenoxy-ethyl ether O-JUZ-NriZ c:rt3 ~:l~z-Lnz-Lnz Menlyllsn-V-pnenoxy m-~,~=mryvriz ethyl ether O-SVz-NHz ~ti3 Ltiz-caiztiz nnemyl m-~~=V~rrriz ~ rnenoxyemyl ether o-SUZ-Nriz Lti3 Ltiz aizriz Memyl m- z c c: ~l-pnenoxyemyl ether o-5Vz-Nrtz cai3 Ltiz tizw;riz nnemyl m- z c.; r-pnenoxyemyl ether o-JVz t12 1;113 1;112-t~ttz-~;ttz ivietnyl m- z N :ri3-phenoxyethyl ether o-~UZ-Nt12 C:H3 ~aiz rtzriz Memyl m- z c.; ~ ~ri3-V-phenoxyethyl ether o-5Uz-NtlZ Ltl3 (.;t12tiztiz a m-~; t, y n--phenoxyethyl ether o-z- z 3 r 3 P m- z - enY
o-z- z 3 z- 3 -p m_C~_~)NHz - eny o-z- z 3 z- 3 -p m-- eny o-z- 2 3 2- 3 3-P m- =~~z - enY
o-z- z 3 z- 3 3- P eny 111- z - -o-r z 3 z- 3 n- eny m- z - -p o-z- z 3 z- 3 P m- z - enY
o-z- 2 3 2- 3 -p m- (=O)NHz - eny o-z- z 3 z- 3 -p m-- eny o-r z 3 z- 3 3-p m-- eny o-z- 2 3 2- 3 3- p eny m-C(=O)NHz - -o-z- z 3 z- 3 n- eny m-- -p z- 2 3 2 3 m p- (~H)NHz - me o-z- z 3 z- 3 -am p-L(=wri)lVriz - me 2- 2 3 2- 3 -anl p-l.(=1V
- lne rl)1V rlz 2 2 3 2- 3 3 p-l~~=lVt1)1Vt12 - a me 2- 2 3 2- 3 3- p-- -and me 2- 2 3 2- 3 n- p- z - -am me 2 2 3 2- 3 m p-~:~=V~rrriz - me _ 2- 2 3 2- 3 -am P- )~Z
' me 2- 2 3 2- 3 -anl p-l.(=V)1Vt12 - lne 2- 2 3 2- 3 3-am p- ~NH2 - llle o-z- z 3 z- 3 3- p- =O)NHz - -am me -o-z- z z- 3 n_ p-C(_O) _ _am z me o-z- z ~s r 3 eny m-C(=NH
- -ammo-carboxylic z acid o-auz-NHz ~ri3 ~;tiz-~H(-LH3)-LI-rnenyl-ammo m-~l=NH)NHz carboxylic acid O-JUz-NHz ~:H3 trHZ-jai(-LH3)-r-pnenyi-ammo m-~l=ivti)Nriz carboxylic acid O-JVZ H2 1:ri3 l:HZ-l:ril-1:H3)-~ti3-pnenyi-ammo m-~l=rVri)Nriz N carboxylic acid O-JUZ-NHz cai3 ~HZ -~ti3)-~H~-u-pnenyi m- z ~Hl ammo carboxylic acid O-JUZ-NHz ~H3 ~;tiz-aril-~ti,)-tsn-u-pnenyi m- z ammo carboxylic acid O-JVZ-NHZ c:H3 ~aiz-LHl-LH,)-rneny-ammo m- z cardoxync acid o-JUZ Hz C.;H3 l;tiz-l:Hl-l:Hj)-l:l-prienyl-ammo m- z N carboxylic acid O-JVZ Hz 1;H3 l:HZ -l:Hg)--p m-N l.;Hl eriy -amino carboxylic acid o-JUz Hz t;ti3 ~;HZ w:113)w;tl3-Pneny-ammo m- z N t_;H1 carboxylic acid o-~Uz Hz (:H3 ~;tiz -~:H3)-~:ri3-u-pnenyl-ammo m- z N fail carboxylic acid o-5Uz-NHz 1:H3 1:H2-l.:H(-1:H3)-tan-U-prieriyl-aIri1I10 m- y carboxylic acid o-z- z CHj CHz-CH(-CH3)-Methyl m-C(=NH)NHz phenoxy-acetic acid ester o-z- z CH3 CHz-CH(-CH3)-Methyl m- z CI-phenoxyacehc acid ester o-z- z CH3 CHz-CH(-CH3)-Methyl m-C(=NH)NHz 1~~-phenoxy-acetic acid ester o-~u2 Hz LH3 Ltiz-~til-~H3)-Metnyi m-~l=mry~riz N ~ri3-pnenoxy-acetic acid ester o-5Uz Hz C:H3 ~:HZ -LH3)-Memym:H3-u-pnenoxy- m- z N ~;Hl acetic acid ester o-5Uz Hz C:H3 ~:Hz-(_:H(-~;H3)-Meuiyl m- z N tsn-u-pnenoxy acetic acid ester o-r z CH3 CHZ -CH3)-Methyl m- z CH( Yhenoxyacetic acid ester o-z- z H3 CHz-CH(-CH3)-Methyl m- z C1-phenoxyacetic acid ester o-z- z Hs z- 3 a m- z - y -p enoxyaceric acid ester o-z- z s z- 3 m-C(=O)NHz - ava ua .
w...
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a Y
3-p epoxy-acetic acid ester o-r z 3 z- s =n-C(=O)NHz - ava ua m.m v a a Y
s--p epoxy acetic acid ester -z- z s z- 3 m-C~ O)NHz - avr ua a L
v as a y n--p epoxy acetic acid ester o-z- z 3 r 3 enoxyacehc m-- aci -o-z- z 3 z- 3 -p m- z - epoxy-aceric aci o-z- z s z- 3 -p m-C( NH)NHz - epoxy-acetic aci z- z s z- 3 3- p epoxy-aceticm-C(=NH)NHz - aci o-z- 2 3 2 3 3 m- 1VFI)NHz - -p epoxy-aceric acid o-z- z s r s n- m-C(=NH)NHz - -p epoxy acetic aci o-z- z , z- , enoxyacehc m- z - aci o-z- z 3 r j -p m-- enoxyacetic aci o-z- z 3 z- , -p m- =O)NHz - enoxyaceric aci o-z- 2 3 2 3 s- p epoxy-aceticm- z - aci o-z- z 3 z- s s- -p epoxy aceticm--aci -o-z- z CH3 z- , n- m-C(=
- -p epoxy acetic acid o-z- z CH3 z- 3 enoxye m~NH)RHz - ano o-z- z s z- s -p m- z - - epoxy-a ano o-z- z s z- 3 -p m- z - epoxy-a ano o-z- 2 3 2 3 ~ri3-pnenoxy-emanoi m- z -o-SOz-R~Z , CF>-z- 3 3- p epoxy-ethanolm-C(=NHjNHz - -o-z- z s r 3 rsn-U-p nenoxy emanoim- z - -o-z- z s z- 3 enoxye m-C( - ano o-z- z 3 r 3 -p m- z - - enoxye ano -o-~ 3 z_ 3 _phenox~y-et m-C(=O)NF~Z
_ anol z- 2 3 2 3 ; p m- z - epoxy-a ano o-~O~-Nzl~ 3 z- j 3= O=plienoxy- m-C(=O)NHz - ethanol -o-r z s z- 3 n- enoXy= m-C(=O)NHz - -P a ano -o-z- z 3 z- 3 a m- =z - Y ..~
p epoxy-a yi ma ua a a um ether o-z- z s z- s m-C( NHjNHz - m ua m.a m a Y
-P
enoxyethyI
ether o-z- 2 3 2- 3 a m-C(=NH)NHz - Y
-P
epoxy-a y ether o-z- z s z- s -m-C(=NH)NHz - ma m i a..ia a a Y
j P
epoxy=
-ethyl ether -o-r z s z- s m-C(_~)~z - ivi ua i ~aa v a Y
-Phenoxy-ethyl ether o-z- z s z- s a m- =NH)IVHZ
- Y
n--p epoxy ethyl ether o-z- z s z- s a m_C(=O)NHz - y enoxye y1 ava ua a a a m ether o-z- z 3 2 3 a - y v~ v~..a -p m-enoxye y ether o-z- 2 3 2 3 a m-C(=O)NHz - Y
_P~~yl ether O-JVz-NHz C:ri3 l:riz-(:ri(-1:ri3)-Mettlyll:ri3 m-phenoxyethyl ether o-JUz-Ntlz l;tlg lalz-lal(-1x13)-lVlelllyl m-l;(=U)1Vt12 1x13 U-phenoxyethyl ether o-5Uz-iVtiz cal3 caiz-Vtl(-c:ri3)-Metny m-~t=v)r~tiz tsn-U-phenoxyethyl ether o-z- z s z- z P m- z - enY
z- 2 3 2- z -p m- =NH)NHz - eny o-z- z 3 z- z -p m-~:(=~ti)mttz - eny o-z- z s z- z s-P m- z - enY
_ o-z- z 3 z_ z 3 p eny m.C(=~)~z _ -o-z- z 3 z- z n- eny m- z - -p _ o-z- z s z- z p m- _ ~~z - eny o-z- 2 3 2- z -p m-~t=U)~riz - eny Y 2 3 2- z -p m-- eny o-2 2 3 2- z s-P m- =O)NHz - enY
o-z- 2 3 2 2 3- p eny m-C(=O)NHz - -o-r z Lri3 z z n- eny m-i.I=U)mriz - -p -o-z z s z- z t p- Z
- me _ o-z- z s z- z -am p_ ~z - me o-z- z 3 r z -am p- )NHz - me o-z- z s z- z 3-am p-~a=wti)mriz - me o-2- z s z- z a- p_ - -~
lne o-z- z s r z n- p_ 2 - -am me o-r z 3 z- z m p- z - me o-z- z 3 r z -am p- )NHz - me o-z- z 3 z- z -am p- )NHz - me o-z- z 3 z- z 3-am p- N z - me - -~
~e o-z- z CH3 z- z n- P-C(=O
- -am me o-r z CH3 r z eny m- z - -ammo-car oxy is acid o-~uz-NHz s z- z eny m- z - -ammo carboxylic acid o-z- 2 3 2- z -p m- riz - eny -ammo carboxylic acid o-z- z m-C(=NH) v11 v11 -111 v11 z s v11~ ~ 11 111 r z 1 p eny -amino --carboxylic acid O-JUz-NHz ~H3 MHz-~Hl-NHZ)-c:H3 m- z u-pnenyi ammo carboxylic acid O-JVZ-Nri2 ~H3 ~riZ -Nriz)-tsn-u-pnenyi m- z ~Hl ammo carboxylic acid o-~uz-NHz uH3 LHz-uHl-NHz)-rnenyi-ammo m-~l=u)wriz cardoxyiic acid o-~uz-Ntiy :ri3 ~aizw;ry-wriz)-~i-pneny-ammo m-~.l=u)ivriz carboxylic acid O-JVz Hz uH3 ~riz-aril-wriz)-r-pnenyi-ammo m-~l=u)wriz N carboxylic acid O-JUZ-Nri2 uH3 ~riz -wriz)-~ri3-pneny-ammo m-~l=u)wriz aril carboxylic acid O-JVZ-Nriz ~ai3 ~rizw:ril-wtiz)w;ti3 m-~;l=v)ivriz u-pnenyi-ammo carboxylic acid o-JUG Hz c:H3 LHz-~:Hl-NHz)-tsn-u-pneny-ammo m-~l=u)mriz N carboxylic acid o-z- z a z- z m-C(=NH)NHz - lYl a y p epoxy-acetic acid ester o-z- z ~ z- z a m-C(=NH)NHz - Y
-p enoxyacehc acid ester o-z- z s z- z iri-C(=NH)NHz - lYl 11~
a y -p epoxy-acetic acid ester o-z- z a z z a m- )NHz - Y
3-p epoxy-acetic acid ester o-~u2-NHz LHj LHz-~Hl-NHz)-a m- z y ,--p epoxy-acetic acid ester O-JVZ-NHZ ~;H3 ~aiz -ivtiz)-metnyi m- z Lril tsn-v-pnenoxy acetic acid ester o-Oz-NHz CHj CHz-CH(-NHz)-Methyl m- z Yhenoxyacehc acid ester o-02-NHz CH3 CHz-CH(-NHz)-Methyl m- z C1-phenoxyacehc acid ester o-z- z CH3 CHz-CH(-NHz)-Methyl m-C(=U)NHz )-phenoxyacehc acid ester o-~uz Hz ~;H, ~aiz-~til-wtiz)-enemy m-~.l=~)mriz N ~ri3-pnenoxy-acetic acid ester O-JVZ-NHZ ~:H3 ~;Hz-c:Hl-wtiz)-metnymai3 m-~,l=u)ivriz v-pnenoxy acetic acid ester O-JUZ-Nriz l~H~ l:Hz -mtiz)-nnetny m-~;l=~)mriz ~,Hl tsn-u-pnenoxy acetic acid ester o-z- 2 3 2- z enoxyacehc m- z - aci o-i z s z- z -p m-C(=NH)NHz - epoxy-acetic aci o-z- 2 3 2- z -p m- )NHz - epoxy-acetic aci z- 2 3 2- z 3-p m-- epoxy-acetic aci o-z- z s r z s- m-C;(=NH)NHz - -p epoxy-acetic acid o-z- z 3 z- z n- m- (=NHjNHz - -p epoxy acetic aci o-z- z 3 z- z enoxyacehc m- z - aci o-z- z 3 z- z -p m- z - enoxyacehc aci o-z- z 3 z- z -p m-- enoxyacehc aci o-z- z s r z 3- p epoxy-aceticm-- aci o-z- 2 3 2- z 3 -p epoxy aceticm- z -aci o-r z 3 z- z n- m- =O z - -p enoxy acetic aci -_ - - z ~3 z_ z enoxye mz _ ano o-z- z ~3 z- z -p m-C(=NH)NHZ
- enoxy-a anoI
o-z- z a z- z -p m~~N~NH2 - enoxy-a anol o-z- z a z- z 3- P m- (= z - enoxy-a ano -o-z- 2 3 2 2 s- - P enoxy-a m-C( - ano o-r z s z- z n- enoxy ethanolm-C(=NH)NHz - -p o-z- 2 7 2 z enoxye m-C(=O z - ano -z- 2 3 2- z -p m-C(=~jNH2 - enoxye -anol o-r z , r z -p m- (=O)N>=I2 - enoxy-a -ano -o-z- z s z z 3-p m-C(=O)NH2 - enoxy-a -ano -o-z- z 3 r z 3- p enoxy- mC( z - - a ano --o-z- z 3 z- z n- enoxy- a ~~O~NHZ
- -p ano o-z- z s r z a ~(=NH)NHz - y p enoxy-a y ether O-JUZ-Nt12 tai, z- z a m- z - y -p enoxye y ether o-z- z a z- z m-C(=NH)NHz - iva m a t-a y -phenoxy-ethyl ether o-z z s z- z a m- (=NH)NHz - Y
3-p enoxy-ethyl ether o-JUZ-NHZ 1x13 Calz l-lVriz)-MeLriyi m-l;l=iVtl)lVtlz tai 1;t13-V-prieriOXy-ethyl ether O-JUz-NHz 1x13 lalz-l~ril-lVriZ)-lVleLilyi m-l:l=1Vri)lVtlz i3ri-u-pnenOXY
ethyl ether o-JVZ-lVri2 ~ai3 ~:nz-~-nl-~nz)-Meuiyi m-~l=m)mriz rnenoxyemyi ether O-JU2-Ntl2 lal3 lalz-fail-lVri2)-lVleLtlyi m-l:l=V)lVriz la-pneriOXyeTriyi ether o-5c~ztiz Lti3 r z a m- z iv - y -p enoxye y ether o-5Vz tiz ~:ri3 r z a m- z N - y 3_ ..
phenoxyethyl ether o-z- z s t z a m-C(=O)~z - Y
s-phenoxyethylether o-z- z s t z m-C(=O)NHz - ...
et it~y 13n-O-phenoxyethyl ether o-z- z a z- - p in- z n eny -o-r z 3 z - -p m- (=NH)NHz n eny -o-z- z s z- - -p m- z n eny _ o-z- z s z- - 3- p m-~:l=i~ti)wtiz n eny -o-z- z s z- - 3_ _ p eny m- z n -o-z- z 3 z- - n_ eny m_ n _p -o-z- z s z- - p m- z n eny -o-z z s z- - -p m-n eny _ o-r z s z- _ -p m_C(=O)NHz n eny _ o-z- z 3 r - 3-P m-~-l=~lwriz n enY
-o-z- z s z- - 3 p eny m- z n --o-z- z s z- - n_ eny m- z n _p -o-z- z s z- - m ~(=NH)NHz n me -o-z- z 3 z- - -am p- z n me _ o-z- z s z- - -am p- 2 n me _ o-z- z a z- - 3-am p-~;l=rrti)~tiz n me -o-2 2 3 2 - 3- p- z n -am - ine o-z- z s z- - n_ p- )NHz n _~
- me o-z- z s z- - i p- =O)NHz n me -o-z- z 3 z- - -am p- z n me _ o-z- 2 3 z- - -am p- z n me _ o-z- z s z- - 3-am p- =O)NHz n me - ~
o-r z 3 z- - n 3- p- =O)NHz - -am me o-z- z s z- - n n_ p- z - -am -me o-r z , z- - n eny m- z - -ammo-car oxy is acid o-5Uz Hz (:H3 LHz-~;H(-rip)-ta-Ynenyl-ammo m- z N carboxylic acid o-SUz-NHz LH3 LHz (-tin)-r-phenyl-ammo m-~(=wri)wriz LH carboxylic acid o-SUz-NHz (:H3 LHz-LH(-tin)-LH3-pnenyt-ammo m-~~=~ri)wriz carboxylic acid o-SUZ Hz LHj MHz-LH(-nn)-~H3-v-pnenyi m- z N ammo carboxylic acid o-SUz-NHz ~;H3 ~:riz-LH(-tsn)-tsn-u-pnenyi m- z ammo carboxylic acid o-~V2-NHZ LH3 LHz-LH(-tsn)-rneny-ammo m- z carooxyuc acid o-5U2-NHZ C:H3 C;H? (-tin)-(_;1-phenyl-ammo m-C:H carboxylic acid o-SUz-NHz C.;H3 c:Hz-LH(-rin)-r-pnenyi-ammo m- z carboxylic acid o-~Vz Hz (.;H3 LHz-LH(-tin)-t,ri3 m- z N pnenyt-ammo carboxylic acid o-5Vz-NHz ~;H3 LHz-LH(-tsn)-3 m- z -p eny -ammo carboxylic acid o-SUZ-NHZ C;H3 C:HZ-C:H(-tin)-n_ m- z -p eny -ammo carboxylic acid o-z- z - CH3 CHz-CH(-Bn)-a m- z y p epoxy-acetic acid ester o-z- z s z- - n a m- z - y -p enoxyacehc acid ester o-2 z 3 CHz-CH(-Bn)-Methyl m- z F-phenoxy-acetic acid ester o-~Uz-NHz c:H3 LHz (-tsn)-Mecnyi m- z c:H ~ri3-pnenoxy-acetic acid ester O-JUZ-NHZ l.Hg l.Hz (-t5n)-lVletllyl m-l.(=lVt1)1Vt12 l;H 1x13 V-pnenOXy-acetic acid ester o-JUz-NHz 1;H3 1:H2-l:H(-tin)-MeLilyl m-l:(=1Vri)iVri2 tin-v-prienOXy acetic acid ester o-~Oi-NHz CH3 CHz-CH(-Bn)-Methyl m-c:(=U)NHz Yhenoxyacehc acid ester o-z- z CH3 CHz (-Bn)-Methyl m- z CH C1-phenoxyacehc acid ester o-z- z CH3 CHZ (-Bn)-Methyl m- z CH F-phenoxyacehc acid ester o-SUz-NHz c:H3 z- - n a m- z - Y
s-P
epoxy-acetic acid ester o-SUz-NHz c:H3 LHZ (-tsn)-a m- z ~H y -P
epoxy acetic acid ester o-5Vz-NHz ~:H3 LHz-c:H(-tsn)-metnyi m- z tsn-v-pnenoxy acetic acid ester o-r z s z- - n enoxyacehc m- z - aci o-z- z s r - n -p m- z - epoxy-acetic aci o-z- z s z- - n -p m-- epoxy-acetic aci o-z- z s z- - n 3- p epoxy-aceticm-- aci o-z- z s r - n 3- m- )1VH2 - -p epoxy-acetic acid o-z- z s r - n n- m- z - -p epoxy acetic aci o-z- z s z- - n enoxyacehc m-C;(=V)NHz - aci o-z- z 3 z- - n -p m- z - enoxyacehc aci o-z- z s z- - n -p m- =O)NHz - enoxyacehc acs o-z- z 3 z- - n 3-p m- )NHz - epoxy-acetic aci o-z- z s z- n 3- m-C(=O)NHz - -p epoxy aceric acid o-z- z s z- - n n- m- z - -p epoxy acehc aci o-r z s z- n enoxye m- z - ano o-z- z 3 - z- n -p m-C(=NH~Hz - epoxy-a ano ri-z- 2 3 2- - n -p m-~~NHz - epoxy-a anol o-z- z a z- - n 3-p m- z - epoxy-a ano o-z- z s z- - n 3- p epoxy-a m-C
- - anol o-z- z s z- - n n- epoxy a m- z - -p ano z- z s z- - n enoxye m-~l=~)Nriz - ano z- 2 3 2- n -p m- z - enoxye ano o-z- z s z- n -p m-C(=O~z - epoxy-a ano o-z- z 3 z- - n s- p m-C(=O)NHz - epoxy-ethanol z- z s z- - n 3- -p m- z - epoxy-a ano o-z- 2 3 2- - n n- m-C(=O~2 - -p epoxy-a anol O-JVy-Nriz uH, ~HZ-~Hl-tin)- a m- z Y
p epoxy-a y ether O-JVZ-NHZ ~:H3 ~HZ-~Hl-tsnJ-Memyma-pnenoxyemyi m- z ether o-~u2 Hz ~:H, Ltizw;ty-tsn)-Memyi m- z N r-pnenoxy-emyi ether o-~uz-NHz ~:H3 Ltiz-~Hl-tsn)-memymai3-pnenoxy- m-~.l=mH)mHz ethyl ether o-JVZ-NHZ 1:H3 1:H2-l:Hl-tSri)-a m-Y
-p epoxy-ethyl ether o-JVz-NHz c:H3 ~;HZ sn)-nnemyi m-~l=r~H)NHz c:Hl-t tsn-V-pnenoxy ethyl ether o-5Vz-NHz c:H3 z - n a m- z - y enoxye y ether o=~Oz-NHZ -- CH3 z- - n a m- z - y -p enoxyet y ether O-5V2-NHz c:H3 z- - n a m- z - y -p enoxye y ether o-5Vz-NHZ C:H3 1;H2-C;HI-tin)-a m-Y
phenoxyethyl ether o-5VZ Hz c:H3 LHz-LHl-~sn)- nnemyi m-~l=~)Nriz N uH3-u-phenoxyethyl ether o-1Uz-NHZ l:Hg 1;H2-l:Hl-lip)- MelllY1 m-l:l=V)lVHz tin-V-phenoxyethyl ether O-JUZ-NHZ (:H3 l:Hz-l:Hl-C:Hz-pnenYi m-~l=Nri)Nriz COOCH3)-O-JUZ-NHZ 1:H3 1:H2-l:Hl-1;H2-l:l-prienYl m-l;l=1VH)1VH2 COOCH3)-O-5U2-NHZ 1:H3 1;H2-l:Hl-1:H2-r-prieriYl m-COOCH3)-O-1U2-NHZ 1.H3 l;Hz-l:Hl-1;H2-3 m-COOCH3)- p enY
o-~u2 Hz LH3 MHz-~Hl-~HZ- ~H3 m- z N COOCH3)- u-pnenyi O-JVZ-NHZ 1:H3 1;H2-l:Hl-l;Hz-tin-v-prienyl m-COOCH,)-O-JVZ-NHZ 1:H3 z- z- p m- z COOCH3)- eny o-z- z s z- z- -p m- z COOCH,)- eny O-JUZ-NHZ 1;H3 l;Hz-l:Hl-l;HZ-r-prienyl m-l;l=V)lVrlz COOCH3)-O-JUZ-NH2 1,H3 z- z- s-P m- z COOCH,)- eny O-JVZ-NHZ 3 2 2 3- m- z COOCH,)- -p eny z ~a z- r n_ u v m _p .~ v~mu o-m eny m-z-COOCH,)-o-~u2 tlz ~:ri3 taiz iz-Anllme p-~l=Nti)Nti2 N tail-t.r COOCH,)-O-JU2-Nriz ~.ri3 ~:riz-~;ril-~:ri2-~;i-anllme p-~l=ivrl)lrri2 COOCH,)-o-JUZ-Nriz 3 z- z- -am p-me COOCH3)-O-JUZ-Nriy 3 Z z- 3-am p-me COOCH3)-o-~UZ Hz ~ri3 ~ri2-aril-~ti2-Ltl3-u-anllme p-~l=Nri)Nri2 N
COOCH3)-o-JUz-NHz s r z- n- p- z -am me COOCH,)-o-JU2-NHZ lai3 z- i m p-me COOCH3)-o-5u2 Hz Ltl, ~;tiz iz-m-anllme p-N ~til-~t COOCH3)-o-JUz HZ 1x13 l;ti2-t_;tll-~;tlz-r-anllme p-N
COOCH,)-O-JUZ H2 1:ri3 lrl2-l~ril-lai2-3 p-N and me COOCH,)-o-JUz-NHz C:rl3 C:rlz-C:rtl-C:rlz-C:rij-u-amine p- z COOCH3)-O-JVZ-NHZ ~ri3 ~aiz-~ril-~ti? rsn-u-amine p-COOCH3)-o-5Vz Hz C.;tl3 ~-riz riz-eny m- z N ~-ril-L -ammo-car oxy is COOCH3)- acid o-5Uz-Nriz Ltt3 c:rlz tz-~i-rnenyl-ammo m- z call-~r COOCH3)- carboxylic acid o-5uz-NHZ c:H3 t;H2-call-cal2-r-phenyl-ammo m-COOCH3)- carboxylic acid o-SUz Hz c:H3 t;Hz-call-~tlz-3-p m- z N eny -ammo COOCH3)- carboxylic acid o-5U2-NHZ C:H3 C.:HZ-C;HI-(:HZ-1:ri3-u-Phenyl m-ammo COOCH3)- carboxylic acid o-5Uz-NHz C:H3 C:Hz iz-tsn-u-phenyl m-~l=lrrl)lvrlz (:Hl-Ca ammo COOCH3)- carboxylic acid o-5Ui HZ cal3 calz l2-rnenyl-ammo m-N t;til-Lt carnoxyllc COOCH3)- acid o-SUZ-NHz C:H3 1:H2-l:Hl-lal2-C:l-phenyl-ammo m-COOCH3)- carboxylic acid o-SUz-NHz C:H3 C:Hz-t;Hl-lalz-r-phenyl-ammo m-~l=~)lvriz COOCH3)- carboxylic acid O-JUZ-NHZ 1:H3 Cal2-l;rll-l:riZ-1:ri3 m-l.l=V)1Vt12 phenyl-amino COOCH,)- carboxylic acid o-5Uz-NHz C:H3 C:Hz-Call-C:riz-1;r13 m- z u-phenyl-ammo COOCH3)- carboxylic acid o-SUz-NHz C;H3 C:Hz-C:HI-C:Hz-tin-u-phenyl-ammo m-C:l=U)lrrlz COOCH3)- carboxylic acid o-z z 3 - CHZ-CH(-CH2-Methyl m-(:(=NH)NHZ
phenoxy-acetic COOCH3)- acid ester o-S02-NHz CH3 CHI CH(-CHz-Methyl m- z C;1-phenoxyacehc COOCH3)- acid ester o-z z CH3 CHz-CH(-CHz-Methyl m- z r'-phenoxy-acetic COOCH3)- acid ester o-2 2 3 2- z- a m-Y
s-p enoxy-COOCH3)- acetic acid ester o-~u2 HZ t;H3 ~t12-~rll-~rlzwvlemyl m-~l=l~ri)mry N ~ri3-u-pnenoxy-COOCH3)- acetic acid ester O-JU2-Nriy al3 ~ahw;ty-pry ivlemyl m-nn-u-pnenoxy COOCH3)- acetic acid ester o-z- z z- , a y enoxyacehc m- z .... z-s COOCH3)- acid ester o-SUz-NHz C:Hj CHz CH(-CHz-Methyl Cl-phenoxyacehcm-C(=U)NHz COOCH3)- acid ester o-SUz-NHz 3 CHz-CH(-CHz-Methyl F-phenoxyacehcm-C(=U)NHz COOCH3)- acid ester O-JUz-wtiz ~.ri, ~riz-~til-Ltiz-nnetnymal3-pnenoxy-m-~;l=v~~riz COOCH3)- acetic acid ester O-JUz-Nriz 3 r z- a Y 3- -P epoxy m- z COOCH3)- acetic acid ester o-~uz-Ntiz ~;ti, ~tizw;tyu;ttznnemyi tsn-u-pnenoxym- z COOCH3)- acetic acid ester o-SOz-NHz s r z- enoxyacehc aci m- z COOCH3)-o-SUz-NHz s z- r -p epoxy-acehc m- z aci COOCH3)-o-SOz-NHz CH3 CHz-CH(-CHZ r'-phenoxy- acehcm-C:(=NH)NHz acid COOCH3)-o-SOz-NHz CH3 CHz-CH(-CHz 3-p epoxy-acehc m- z aci COOCH3)-o-SOz-NHz CH3 CHz-CH(-CHz-3- -p epoxy-acehcm-C:(=NH)NHz COOCH3)- acid o-z- z CHa CHz-CH(-CHz-Bn-U-phenoxy m- z acehc acid COOCH3)-o-SOz-NHz CH3 CHz-CH(-CHz-Yhenoxyacehc m- z acid COOCH3)-o-2 z CH3 CHz-CH(-CHz-Cl-phenoxyacehc m- z acid COOCH3)-o-S~P ITi- CH3 CHz-CH(-CHz-1'-phenoxyacehc m-C;(=U)NHz acid COOCH,)-o-z- z CH3 CHz-CH(-CHz-CH3-phenoxy-acehcm- z acid COOCH3)-o-z- z CH3 CHz-CH(-CHz-CH3-U-phenoxy m- z acehc COOCH,)- acid o-z- z CHs CHz-CH(-CHz-Bn-U-phenoxy m- z acehc acid COOCH3)-o-SUz-NHz C;H3 C:Hz Hz-enoxye ano m- z c:Hl-L
COOCH3)-o-SUz-NHz C;H3 z r -p epoxy-a ano m- z COOCH,)-o-z- z s z- z- -p epoxy- a ano m- z COOCH3)-o-SUz Hz cai3 t;tiz-pail-~;tiz-3-p epoxy-a ano m- z N
COOCH3)-o-SUz-NHz c:H3 caiz-l;tilWtizW;ti3-u-pnenoxy-emanoim- z ;
COOCH3)-o-SUz-NHz C:H3 r z n- -p epoxy a m- z ano COOCH3)-o-SUz-NHz c:H3 ~tiz-aril-~riz-enoxye ano m- z COOCH3)-o-SUz-Nriz c:H3 Ltlz-call-Ltlz-c:1-pnenoxyemanoim- z COOCH,)-o-SUz-NHz C;H3 c:Hz-~;Hl-LHz-r-pnenoxy-emanoim- z COOCH,)-o-SUz-NHz C:H3 C;HzW i? 3-p epoxy-a ano m- z :Hya COOCH3)-o-SUz-NHz (:H3 c:Hz riz-Lns-u-Pnenoxy- m- z Cail-~ emanoi COOCH3)-o-SUz-NHz c:H3 c:Hz-Ltil-Ltiz-tsn-u-pnenoxy- m- z emanoi COOCH3)-O-SUZ-NHZ c:H3 c:Hz-Ltil-Ltiz-Merry pnenoxy-emyim- z COOCH3)- ether o-z- z CH3 z- z- a y -p enoxye m- z y COOCH3)- ether o-~uz-Nriz ~n3 ~riz-~ry-~ry-nnecnyi r-pnenoxy-emyim-~l=ivriJNriz COOCH3)- ether o-~uz-Nriz Sri, ~riz-aril-~ri2 nnetnyi ~ri3-pnenoxy-m-~l=NriJNriz COOCH3)- ethyl ether o-~uz-Nttz ~ri3 ~riz-~til-~tiZ memyi ~ti3-u-pnenoxy-m-~;l=NriJNtiz COOCH3)- ethyl ether O-JUZ tiz uri3 uriz-aril-utiz-Memyi isn-u-pnenoxym-ul=Nri)Ntiz N
COOCH,)- ethyl ether O-JVz-Nriz ~ri3 ~riz-aril-~riz-enemy rnenoxyemym-~l=u)Nriz COOCH,)- ether O-JVZ-Nriy ;rij ~;riz-aril-~riz-nnemyi m-pnenoxyemyim-~l=uJivriz COOCHj)- ether O-JVZ-lVri2 ~-ri3 Lri2'~-ril'~-riz-nnetnyi r-pnenoxyewyim-~:l=uJNriz COOCH3)- ether O-JUz-Ntiz ~ri3 ~riz-aril-~riz Metnyi ~ri3- m- z COOCH,)- phenoxyethyl ether o-~uz-Nttz ~ti3 ~aiz-aril-~tiz-Memyi ~rij-V- m- z COOCH3)- phenoxyethyl ether o-z- z s z- 2 a y n-m m m v-COOCH3)- phenoxyethyl ether O-JVz-ivtiz ~;ri3 ~aiz-~atl-~:riz-pnenyi m-~.l=mnyvriz CHz-OH)-O-~Uz-Nriz s z- z- -p eny m- z CHz-OH)-O-JUZ-Nt12 liri3 1;ri2-l;ril-1:ri2-r-pnenyi m-~:l=ivri)ivriz CHz-OH)-O-JUz-Nriz ~ri3 ~riz-aril-~riz-3-p eny m- z CHZ OH)-O-JUZ-iVriz ~ti3 ~riz-~ril-~riz-~ri3-u-pneny m- z CHz-OH)-O-~Uz-Nriz uri3 urtz-aril-uriz-isn-u-pnenyi m-~l=ivri)ivriz CHz-OH)-O-JUZ-NriZ Lti3 ~tiz-~til-~ri2 pnenyi m-~.l=uJivriz CHz-OH)-O-JUz tiz ~ti3 ~iiz-c:ril-~riz-m-pnenyl m- z N
CHZ OH)-o-~Vz-Nrlz ~r13 ~riz-~rll-~rlz-r-pnenyi m- z CHz-OH)-O-JUy-NriZ ~ai3 ~aiz-~til-~ri2-~:ri3-pnenyi m- z CHz-OH)-o-~uz-Ntiy ai3 z- z- 3- -p eny m- z CHz-OH)-O-~Uz-Nriz ~ri3 ~riz-aril-~tiz-n_ _p eny m- z CHz-OH)-o-JUZ-Nrtz 3 z- r m me p-CHz-OH)-o-~Uz-tvtiz s z- r -am me p- z CHz OH)-o-JUZ-iVrlz ~ri3 ~ri2-pry-~ri2-r-amime p-~l=ivriJivriz CHz-OH)-o-JUZ-lVr12 1:r13 2- z- 3-am me p-CHz-OH)-O-JVz-Nriz , z- z- 3 -am me p- z CHz-OH)-o-~UZ ttz url3 uriz-urll-ur1z isn-u-amlme p-~l=NriJNnz N
CHz-OH)-O-JUZ-iVr12 1x13 uri2-aril-uriz-Amime p-ul=vyvriz CHz-OH)-o-~uz-Niiz ~ti3 ~aiz-aril-~:riz-t,i-amnne p-t.l=v)ivriz CHz-OH)-z- 2 3 2- z- -am me ..
p-CHz-OH)-o-SUz-NHz C.:H3 (:Hz-C;H(-C:Hz-C:H3-anllme p-l:(=U)iVriz CHz-OH)-o-SUz-NHz s z- z- 3 p- z -am me CHz-OH)-o-SUz-NHz s i z- n- p- z -am me CHI OH)-O-SUZ-NHz C:H3 l;Hz Hz-eriy m- z l;H(-l: -ammo-car Oxy CHz-OH)- acid o-SUz-NHz c:H3 LHz t;H(-t;Hz-Li-rnenyi-ammo m- z CHz-OH)- carboxylic acid O-5Uz-NHz ljH3 (:Hz riz-r-pnenyi-ammo m-l:H(-l CHz-OH)- carboxylic acid O-5Uz-NHz 1;H3 (:Hz-l;H(-l;Hz C;H3-pnenyi-ammo m- z CHz-OH)- carboxylic acid o-5Uz-NHz C:H3 l:Hz-C:H(-l:Hz-c:H3-u-pnenyi m- z ammo CHz OH)- carboxylic acid o-SUz-NHz ~:H3 ~:Hz-LH(-~:Hz-tsn-u-pnenyi m- z ammo CHz-OH)- carboxylic acid o-5Vz-NHz C:H3 C;Hz-l:H(-l:Hz-Ynenyi-ammo m-l:l=U)lVriz CarbOXyllC
CHz-OH)- acid o-5uZ Hz c:H3 LHZ c:H(-LHz-m-pnenyi-ammo m- z N
CHz-OH)- carboxylic acid o-JVz-Nriz Lti3 MHz c:H(-MHz-r-pnenyi-ammo m-~l=~yvriz CHz OH)- carboxylic acid o-5uz-NHz c:H3 ~Hz-c:H(-MHz ~H3-pneny-ammo m- z CHz-OH)- carboxylic acid O-5Uz-NHz (:H3 l;Hz Hz 1:ri3-V-pneriyi-ammo m- z C.;H(-l;
CHz-OH)- carboxylic acid o-JVz-NHz (:H3 l;Hz-C;H(-l;Hz-tan-u-prieriyi-ammo m- z CHz-OH)- carboxylic acid o-z z ; BIZ-CH(-CHz Methyl m- z phenoxy-acetic CHz-OH)- acid ester o-r z s CHz CH(-CHz-a m- z y -p enoxyacehc CHz-OH)- acid ester o-z- z s CHz-CH(-CHz-Methyl m- z F-phenoxy-acetic CHz-OH)- acid ester o-JVZ Hz 1;H3 l;Hz-l;tl(-1;ri2lVleTnyi m- z N 1;r13-pnenOXy-CHz-OH)- acetic acid ester .
O-JVz-Nriz c:H, MHz c:H(-MHz-ivietnyi m- z ~ryu-pnenoxy-CHz OH)- acetic acid ester o-5Uz-NHz c:H3 ~:Hz-LHIw:Hz-Merry m-~(=tvryvriz tsn-u-pnenoxy CHi OH)- acetic acid ester o-SOz-NHz CH3 CHz-CH(-CHz-Methyl m-(:(=U)NHz Yhenoxyacehc CHz-OH)- acid ester o-z- z CH3 CHz-CH(-CHz Methyl m- z Cl-phenoxyacetic CHz-OH)- acid ester o-z- z s CHz CH(-CHz-Methyl m- z F-phenoxyacetic CHz-OH)- acid ester o-~u2 Hz c,H, uHz-c:ri(-uriz-Merry m-~t=u~wriz N ~ri3-pnenoxy-CHz-OH)- acetic acid ester o-r z s z- z- a m- z Y
-p epoxy CHz-OH)- acetic acid ester o-DUz-NHz c:H3 ~aiz-cai(-Ltizivietnyi m-~~=uyvriz nn-u-pnenoxy CHz-OH)- acetic acid ester o-2 z CH3 CHz-CH(-CHz-Phenoxyacetic m-C(=NH)NHZ
acid CHz-OH)-o-OZ-NH2 CH3 CHz CH(-CHz-Cl-phenoxy-acetic m-C(=NH)NHz acid CHz-OH)-o-r 2 3 z- z- -p m- )NHz epoxy-acetic aci CHz-OH)-o-z- z LHs z- z- 3-p enoxy-aceticm- z aci CHz-OH)-o-SUz-NHz 3 (:Hz-(:H(-C;Hz-(:H3-U-phenoxy-aceticm-C;(=NH)NHz CHz-OH)- acid o-SUz-NHz ~ C;H2 Hz-13n-U-phenoxy m-(:(=NH)NHz LH(-(: acetic acid CHz-OH)-o-SVz-NHz j C:Hz-C;H(-C:Hz-Yhenoxyacehc m-(_:(=U)NHz acid CHz-OH)-o-5Uz-NHz 3 C;Hz Hz-(:I-phenoxyacehcm-C:(=U)NHz C;H(-L acid CHz-OH)-o-5Uz-NHz s z z- -p enoxyacehc m- z aci CHz-OH)-o-~Uz-NHz C;H3 C:Hz-C:H(-C;HZ C;H3-phenoxy-aceticm-C:(=U)NHz acid CHz-OH)-o-SUz Hz C;H3 r r 3- -p enoxy aceticm- z N
CHz-OH)- acid o-SUz-NHz C;H3 (:Hz-C:H(-C;Hz-tan-U-phenoxy m-C:(=U)NHz acetic acid CHz-OH)-O-JVz-wriz ~ri3 z- z- enoxye ano m- z CHz-OH)-O-JVz-wriz uri3 uriz-aril-uriz-m-pnenoxy-emanoim-ul=wrywriz CHz-OH)-o-~uz-Nry uns ~-nraril-~-na-r-pnenoxy- emanoim-ul=wrywriz CHz-OH)-o-~uz-Ntiz t,ti3 ~aiz-t.;til-~tiz-tai3-pnenoxy-emanoim-~:l=mtyvriz CHZ OH)-O-JVZ riz uri3 ~nz-aril-uriz-url3-u-pnenoxy-emanoim-~l=NriJwriz w CHz-OH)-o-~uz-Nriz uns urirunl-~nr ~sn-u-pnenoxy m-ul=wrywtiz emanoi CHz-OH)-O-JU2-Nriz uri3 uriz riz-rnenoxyemanoi m-ul=ulwriz ury-~
CHz-OH)-o-auz-lVtiz Lti3 ~riz-~nl-~riz-~l-pnenoxyemanoim- z CHz-OH)-o-z- z s z- z- -p enoxy-a ano m- z CHz-OH)-o-z- 2 3 2- z- s-p enoxy-a ano m- z CHz-OH)-o-JIJZ-iVriz l.rig l.rlZ-l.rll-1.r12-~:ri3-u-pnenoxy-m-~.l=uyvnz emanoi CHz-OH)-O-JVz-lVriz Lti3 r r n- -p enoxy- m- z a ano CHz-OH)-O-JVz tiz pry z- z- a y p enoxy-a m- z w y CHz-OH)- ether O-JVz ttz ~rij ~riz-aril-~rizMetnyi m-pnenoxyemyim- z N
CHz-OH)- ether o-~uz-Ntiz t_;ti, unz-~nl-unz-Merry r-pnenoxy-emyim- z CHz-OH)- ether O-JVZ-Ntiz jai, t.riz-~:ril-~;riz-Memym;rij-pnenoxy-m-t.l=mryvriz CHz-OH)- ethyl ether O-JUz-lVriz ~:ri3 ~-nz-~-ril-~-nr Memym-ri3-v-pnenoxy-m-Ll=lVt1)lVrlz CHz-OH)- ethyl ether O-JUZ-1Vt12 Lti3 unz-unl-~nz-Merry rsn-u-pnenoxym-ul=wrywriz CHz-OH)- ethyl ether o-JUz-1Vt12 ~ri3 ~r12-~rll-~ri2-Merry rnenoxyemyim-~l=u~Nriz CHz OH)- ether O-JUz tiz uri3 uriz-uril-~riz-Merry m-pnenoxyetnym-ul=u~wtiz w CHz-OH)- ether O-JUz-wtiz ~ti3 uriz-uril-~nz-Merry r-pnenoxyemyim-ul=u~wriz CHz-OH)- ether o-~u2 riz cai3 utiz-aril-utiz-Merry uri3- m-ul=u~wriz w CHz-OH)- phenoxyethyl ether o- z- z ns z- z- a Y 3 m- z CHz-OH)- phenoxyethyl ether O-JUz-Nrl2 t,ri3 ~;riz-jai(-~;tizMetnyi tsn-u- m-~(=u~wtiz CHz-OH)- phenoxyethyl ether O-JUz-iVri2 ~:ri3 ~tiz-t_;rs(-~:riz-pnenyi m-~:(=mtyvtiz C(=O)-N-morpholino)-O-JUz-Nriz ~ri3 ~riz-Sri(-~riz-m-pnenyi m-~(=wri~Nriz C(=O)-N-morpholino)-O-JUz-Nriz ~;ri3 ~riz-t,ri(-~riz-r-pneny m-~,(=mryvriz C(=O)-N-morpholino)-o-~uz-Ntiz Lti3 Ltiz-~;ti(-Ltiz-t_ai3-pnenyi m-~;(=mrywriz C(=O)-N-morpholino)-o-JUz-Ntiz url3 ~rtz-ur1(-~rlz-uri,-u-pneny m-~(=wrywriz C(=O)-N-morpholino)-o-~Uz-Ntiz Lti3 Ltiz-t,ti(-Lri2tsn-u-pnenyi m-~(=mriyvriz C(=O)-N-morpholino)-O-JUZ-Ntl2 Lti3 Ltiz-~:ri(-Ltiz-pnenyt m-~.(=a yvriz C(=O)-N-morpholino)-o-JVz 1Vt12 (a13 (:rlz-tJr1(-~alz-tri-pnenyi m-t,(=uyvtiz C(=O)-N-morpholino)-o-5V2-Nri2 Lti3 t;tiz-~;ti(-~;tiz-r-pnenyi m-~(=uyvriz C(=O)-N-morpholino)-O-JUZ-Ntl2 lai3 1x12-l;ri(-1;t12-lal3-prieriyl m-l:(=u)lVtlz C(=O)-N-morpholino)-o-~uz-Ntiz jai, ~;riz-tai(-~;tiz-~:n3-u-pnenyi m-L(=uJlvriz C(=O)-N-moipholino)-O-JUz-lVri2 Lti3 Ltiz tayu;tizrsn-u-pnenyi m-~.(=uyvriz C(=O)-N-morpholino)-O-JUZ-Nri2 Lri3 ~tiz-uri(-urizAmime p-~(=wrywriz C(=O)-N-morpholino)-O-JUZ-1VY12 (..Y13 l,rl2-l.rl(-l.rlz-L;~-an111l1e p-l.(=lVt1)lVri2 C(=O)-N-morpholino)-O-JUZ-Nti2 Lti3 ~ttz-uri(-~tiz-r-amime p-~(=wti~wriz C(=O)-N-moipholino)-O-JUz-Ntl2 l;tig l:riz l;rl(-1x12-l:rlg-amllrie p-L(=lvri)lvriy C(=O)-N-morpholino)-o-~uz-Ntiz cai3 uriz-uri(-~riz-~ri3-u-amime p-~(=wryvriz C(=O)-N-morpholino)-O-JUZ-Nrl2 Lti3 ~;tiz-~:ri(-t,tiz-tsn-u-amime p-~;(=mryvriz C(=O)-N-morpholino)-o-~uz-Ntiz ~ri3 uriz-Sri(-~riz-Amime p-~(=u~wriz C(=O)-N-morpholino)-n- z- 2 3 2- r -am me p- NHz = 221 -moipholino)-O-JVz-Nriz ~.ri3 ~riz-aril-~riz-r-amime p-~l=u)mriz C(=O)-N-morpholino)-o-JUz-Nriz ~ri3 ~riz-aril-~riz-~ti3-amime p-~.:1=u)Nriz C(=O)-N-morpholino)-o-auz-Ntiz ~:ri3 ~riz-aril-~riz-uri3-u-amime p-~l=u)wriz C(=O)-N-morpholino)-O-JUz-Nrlz 1:ri3 l:riZ-l;tll-lalz-lin-u-amllrie p-l:l=u)lVrlz C(=O)-N-morpholino)-O-JUz-LVtlz ~-ri3 ~-ri2-~-ril-~-riYrneny-ammo-carooxyucm-~;l=wti)wtiz C(=O)-N- acid morpholino)-O-JUZ-lVtlz 1:r13 Lri2-Lril-Lri2-l.l-Ynenyl-amlIlOm-l.l=lVr1)lVtiz C(=O)-N- carboxylic acid morpholino)-O-JUz-lVtiz 1;r13 ~aiz-~:ril-~:riz-r-pnenyi-ammo m-~:l=ivri)ivriz C(=O)-N- carboxylic acid morpholino)-O-JVz-NHz ~ai3 ~:rtz-pail-~aiz-~-n,-pnenyi-ammom-~;l=ivri)wriz C(=O)-N- carboxylic acid moipholino)-O-JUz-Nriz ~:ri3 t,riz-t,ry-~ry-t,ri,-u-pnenyi m-~.l=ivri)ivriz ammo C(=O)-N- carboxylic acid morpholino)-o-JVz-NHz llri3 ~;riz-pail-Ltiz-tsn-u-pnenyi m-~;l=ivri)ivriz ammo C(=O)-N- carboxylic acid morpholino)-O-JUz NHz l.ri3 l;tlz-l:ril-l:tlZYnenyl-ammo CarDOXyIICm-l:l=u)lVrlz C(=O)-N- acid morpholino)-o-JUz-Nriz ~;ti3 ~:rtz-~;til-~tiz-ta-pneny-ammo m-~l=u)mriz C(=O)-N- carboxylic acid morpholino)-o-JUz-Nriz uri3 urtz-~:ril-~riz-r-pneny-ammo m-~l=u)wriz C(=O)-N- carboxylic acid morpholino)-O-JVz-lVriz 1:ri3 1;ri2-l;ril-l:riz-~:ri3-pnenyi-ammom-~:l=u)ivriz C(=O)-N- carboxylic acid morpholino)-O-JUz-Nriz Lri3 ~aiz-~-ttl-Lriz-~n3-~-Pneny-ammom-~;l=u)ivriz C(=O)-N- carboxylic acid morpholino)-o-~uz-Ntiz uri3 uriz-aril-~riztsn-u-pnenyi-ammom-~l=u)ivriz C(=O)-N- carboxylic acid morpholino)-o-SOz-NHz CH3 CHz-CH(-CHz-Methyl phenoxy-aceticm-(:(=NH)NHz C(=O)-N- acid ester morpholino)-o-SOz-NHz CH3 CHz-CH(-CHzMethyl Cl-phenoxyacehcm-C(=NH)NHz C(=O)-N- acid ester morpholino)-o-SOz-NHz CH3 CHz-CH(-CH2Methyl r'-phenoxy-m-C(=NH)NHz acetic C(=O)-N- acid ester morpholino)-o-~uz-Ntiz uri3 urir~-ril-~nz-MemYi ~-n3-pnenoxy-m-l~l=lVr1)lvri2 C(=O)-N- acetic acid ester morpholino)-o=S~ CH3 z- z- a y 3- -p enoXy=-m-~N-- Hz C(=O)-N- acetic acid ester morpholino)-O-JUz-mriz ~:ri3 ~aiz-pail-Lti2Memyi nn-u-pnenoxym-~;l=NtyNtiz C(=O)-N- acetic acid ester morpholino)-o-SOz-NHz CH3 CHz-CH(-CHz-Methyl Phenoxyacehcm-C(=U)NHz C(=O)-N- acid ester morpholino)-o-SOz NHz CH3 CHz-CH(-CHz-Methyl Cl-phenoxyaceticm-C(=U)NHz C(=O)-N- acid ester morpholino)-o-SOz-NHz CH3 CHz-CH(-CHz-Methyl l~-phenoxyacehcm-C(=U)NHz C(=O)-N- acid ester morpholino)-o-auz-Nriz ~ri3 ~ri2 aril-~riz-memym;rij-pnenoxy-m-~l=u~rrriz C(=O)-N- acetic acid ester morpholino)-O-JVZ-NHZ Lti3 caiz-~ry-~ry-nnemyi ~ri3-u-pnenoxym-~l=u~wriz C(=O)-N- acetic acid ester morpholino)-O-JVZ-NHZ Lti3 ~tiz-~til-~tiz-Memyi tsn-u-pnenoxym-~l=u~wriz C(=O)-N- acetic acid ester morpholino)-o-SOz-NHz CH3 CHz-CH(-CHzPhenoxyacetic m-C(=NH)NHz acid C(=O)-N-morpholino)-o-SOz-NHz CH3 CHz-CH(-CHz-Cl-phenoxy-aceticm-C:(=NH)NHz acid C(=O)-N-morpholino)-o-SOZ NHz CH3 CHz-CH(-CHz-F-phenoxy- aceticm-C(=NH)NHz acid C(=O)-N-morpholino)-o- z- z CH3 CHz-CH(-CH2CH3-phenoxy-aceticm-C(=NH)NHz acid C(=O)-N-morpholino)-o- z- z CH3 CHZ CH(-CHz-CH3-O-phenoxy-aceticm-C(=NH)NHz C(=O)-N- acid morpholino)-o- Oz-NHZ CH3 CHz-CH(-CHZBn-U-phenoxy m-(:(=NH)NHz acetic acid C(=O)-N-morpholino)-o- z- z CH3 CHz CH(-CHz-Phenoxyacetic m-C(=U)NHz acid C(=O)-N-morpholino)-o- z z CH3 CHz-CH(-CHz-Cl-phenoxyacehc m-C(=U)NHz acid C(=O)-N-morpholino)-o-SOz NHz CH3 CHz-CH(-CHz-r'-phenoxyacehc m-C(=U)NHz acid C(=O)-N-morpholino)-o-~O~ NHZ CH3 CHz-CH(-CHz-CH3-phenoxy-aceticm-C(=U)NHz acid C(=O)-N-morpholino)-o- z- z s CHz-CH(-CHzCH3-U-phenoxy m-C(=U)NHz acetic C(-0)-N- acid morpholino)-o-SOz-NHZ CH3 CHz-CH(-CHz-13n-U-phenoxy m-(:(=U)NHz acetic acid C(=O)-N-morpholino)-o-JUz-Nriz 3 z- z- enoxye ano m- z C(=O)-N-more o mo -o-~uz-rVriz ~ri3 ~riz-~ry-~tiz-Li-pnenoxy-emanoim-~l=NryNtiz C(=O)-N-morpholino)-O-JUz-Nriz ~ri3 ~riz-aril-~riz-r-pnenoxy- emanoim-~:l=mtiyvtiz C(=O)-N-morpholino)-O-JUz-wriz ~ri3 ~riz-aril-~riz-uri3-pnenoxy-emanoim-~;l=r~riJwriz C(=O)-N-morpholino)-O-JUz-wriz ~r13 ~:rizw:ry-~tiz-~r13-u-Pnenoxy-emanoim-~.~=mryrVriz C(=O)-N-morpholino)-o-JUz-Nriz ~:ri3 ~:rlz-call-~tiz-tsn-u-pnenoxy m-~:~=mryrrriz emanoi C(=O)-N-morpholino)-O-JUZ-lVYlz Lri3 ~'ri2-Lril-Lri2-rnenoxyemanoi m-~~=uyvriz C(=O)-N-morpholino)-o-~uz-Ntiz ~ri3 uriz-~ry-~riz-~i-pnenoxyemanoim-~~=ulwriz C(=O)-N-moipholino)-o-~Vz-lvriz Lri3 Lnz-unl-unrr-pnenoxy-emanoim-~l=u~wriz C(=O)-N-morpholino)-o-~u2 NHz Lti3 ~;ttz ~;ril-Ltiz-~ai3-pnenoxy-emanoim-~l=uJmriz C(=O)-N-morpholino)-O-JUz-Nrlz urij utiz-aril-uriz-~ri3 u-pnenoxy- m-~l=a ~wriz emanoi C(=O)-N-morpholino)-O-JUz-Nrl2 uric unz-uril-~nz-~n-u-pnenoxy- m-~~=u~rrriz emanoi C(=O)-N-morpholino)-o-~Vz-Nriz t;ti3 Lriz-Ltil-utiz-nnemyi pnenoxy-emyim-~~=wrywtiz C(=O)-N- ether morpholino)-o-5Uz-NHz t;ri3 caiz-Ltil-LtizMemyi m-pnenoxyernyim-~l=wri~rrriz C(=O)-N- ether morpholino)-o-JUz-NHz cai3 ~:rizway-Ltiz-enemy r-pnenoxy-emym-~:~=mryvriz C(=O)-N- ether morpholino)-o-~u2 lvtiz t;ti3 Lry~til-~riz-nnemyi ~ri3-pnenoxy-m-~l=mryvriz C(=O)-N- ethyl ether morpholino)-o-JUz-Nriz c:rl3 ~riz-pail-~riz-enemy ~ri3-u-pnenoxy-m-~~=ivryvriz C(=O)-N- ethyl ether morpholino)-O-~Uz-Nriz Lti, utiz-aril-uriz-Memyi tsn-u-pnenoxym-~~=wryvriz C(=O)-N- ethyl ether morpholino)-O-~Vz-Nriz t;ti3 ~riz-~rll-~rlz-Memy rnenoxyetnym-~l=u~rVriz C(=O)-N- ether morpholino)-o-auz-Nriz ~ti3 ~riz-~ry-~rizMemy m-pnenoxyemym-~~=uyvriz C(=O)-N- ether moipholino)-O-~Uz-Nrlz Lti3 Ltiz-~til-~tiznnemyi r-pnenoxyemyim-~l=uyvmz C(=O)-N- ether moipholino)-o- 2 2 3 2- r a Y s- m- z p enoxyet y a er morpholino)-O-JVZ lVtlz 1.ri3 l:riz-l.;tl(-l.rlz-Memyl l.rl3-V- m-l.~=V)1Vr12 C(=O)-N- phenoxyethyl ether moipholino)-O-JUz-mtiz 1Jr13 l:riz-t,ri(-t,tiz-iviemyi tsn-u- m-~;(=Vyvtiz C(=O)-N- phenoxyethyl ether morpholino)-o-JVZ Ntlz Calj l:tlz-Cal(-Calz-phenyl m-l:(=Nti)Ntlz CHz-S(O)z-CH, O-JVi Nriz j l:riz-Sri(-l:riz-la-pnenyi m-~(=wri)Nriz CHz-S(O)z-CH, O-wz-ivtiz t,rl3 l;riz-tai(-t_;tiz-r-pnenyi m-~;(=wrywriz CHz-S(O)Z
o-~u2-Nriz 1a1, laiz-Sri(-l:riz-1;r13 pnenyi m- z CHz-S(O)z-CH3 O-JUz-Nriz jai, l:riz-l:ri(-l:riz-1:r13 u-pnenyi m- z CHz-S(O)z-CH3 o-JUZ-Nriz s z- z- n- -p eny m- z CHz-S(O)z-CH3 o-JVZ-Nri2 1x13 lain lai(-laiz-pneny m-~~=Vyvriz CHz-S(O)Z
o-JVz-NriZ l:ri3 z- z- -p eny m- z CHz-S(O)z-CH3 O-JVZ-Nriz 1x13 z' Y -p eny m- z CHz-S(O)z-CH3 o- z- z a z- z- s-p enY m- z CHz-S(O)z-CH3 o-JUZ-Nri2 t;ti3 laiz-t;ti(-t_;tiz-3- -p eny m- z CHz-S(O)2 o-~uz-Ntiz 1:r13 l:riz-l:ri(-l:riz-rsn-u-pnenyi m- z CHz-S(O)z-CH3 o-~u2 Ntlz 1:ri3 z- z- m me p- z CHz-S(O)z-CH3 o-JVz Ntiz 1:ri3 Cain lai(-lai2-l:l-aI111me p-CHz-S(O)z-CH3 o-JU2-Ntl2 1.113 1.112-l.rl(-l.rl2-r-amlme p-l:~=lVr1)lvrl2 CHz-S(O)rCH3 O-JV2-Nriz 1x13 l:riz-l:ri(-l:riz-1:r13-amnne p- z CHz-S(O)z-CH3 o-~uz-Ntiz t_;ti3 l:riz-l:ri(-laiz-1:r13-u-amime p- z CHz-S(O)z-CH3 o-JUz-Nriz (_a13 laiz-lai(-laiz-tin-u-anllme p- z CHz-S(O)z o-JUz-Ntiz lai3 z' z- m me p-CHz-S(O)z-CH3 o-JVZ-Ntl2 s z- z- -ani me p-CHi S(O)z-CH3 o-1Uz-Nti2 1x13 1x12-Cal(-lalz-r-amlme p-l;(=u)iVrlZ
CHz-S(O)z-CH3 o-JUz Nti2 C:rig 1x12-l;ti(-1x12-1x13-amlme ~ p- z CHz S(O)z-CH3 O-JUZ-Ntiy laig 1:ri2-l;rl(-1;r12-l:rlg-u-anllme p-CHz-S(O)z-CH3 O-lUz-Ntiz 1x13 l;ti2-l:rl(-1:r12-tSn-u-arillme p- y CHz S(O)z-CH, o-JU2-Ntl2 1x13 lalz-lal(-1;ri2-Yrienyl-ammo-CarDOXyIICm-l:(=lvrl)1vt12 CHz-S(O)2 acid CH, O-JUZ-Ntl2 1;113 1x12-lal(-1~t12-l.l-Ynenyl-ammo m-l.(=lVt1)iVrlz CHz-S(O)2 carboxylic acid o-JVz Ntlz 1;t13 l;riz-lal(-lain-r-pnenyl-ammo m-l;(=lVr1)1Vr12 CHz S(O)z-CH3carboxylic acid CH3 z- z- 3-p m-C(=~)~z .~ .,.. eny o- z- z -amino -,.~.
..
CHz-S(O)z-CH3carboxylic acid o- z- z 3 z- z- 3- m- z -p eny ammo CHz S(O)z-CH3carboxylic acid O-JVz-Nriz ~:ri3 ~;riz-Lrll-Lrlz-tsn-u-pnenyl m-~;l=rVryl~riz ammo CHz-S(O)z-CH3carboxylic acid o-JVz-Nriz s r r eny m- z -ammo car oxy is CHz-S(O)z-CH,acid o-~Vz-Nriz ~ri3 ~ti2 ~Hl-~tiz-m-pneny-ammo m-~l=~~Nriz CHz-S(O)z carboxylic acid o-at~z NHz ~ri3 ~tiz-aril-~tiz-r-pnenyi-ammo m- z CHz-S(O)z carboxylic CH3 acid o-JVz Ntiz c:ri3 ~tiz ~til-~ttz-~ri3-pnenyi-ammo m-~l=~~Nriz CHz-S(O)z-CH3carboxylic acid O-JVz-Nriy 1:r13 l:riz-tall-1:ri2-~ai3-v-pnenyi-ammo m-~;l=vJ~riz CHz S(O)z-CH3carboxylic acid O-JVZ-Nriz ~ri3 ~riz-~til-catz-tin-v-pnenyi-ammo m-~l=v~~riz CHz-S(O)z-CH,carboxylic acid o-SOz-NHz CH3 CHz-CH(-CHz-Methyl m-C(=NH)NHz phenoxy-acetic CHZ S(O)2 acid CH3 ester o-SOz-NHz CH3 CHz-CH(-CHz-Methyl m-C(=NH)NHz Cl-phenoxyacehc CHz S(O)z-CH3acid estei o-SOz-NHz CH3 CHz-CH(-CHzMethyl m-C(=NH)NHz l~-phenoxy-acetic CHz-S(O)z-CH3acid ester z- 2 3 2- z- a m- z Y
a-P
epoxy-CHz-S(O)z-CH3acetic acid ester O-JUZ-NH2 c:H3 ~aiz-pail-caizMetnym;ti3-u-pnenoxy- m-~:l=rrrywriz CHz S(O)z-CH3acetic acid ester o- r z s z- z- a m- z y n--p epoxy CHz-S(O)z acetic CH3 acid ester o- 2 NHz CH3 CHz-CH(-CHz-Methyl m-C(=U)NHz Yhenoxyacehc CHz-S(O)z-CH3acid ester -NHz CH3 CHz-CH(-CHz-a m- z y -p enoxyacehc CHz S(O)z acid CH3 ester o-SUz-NHz CH3 CHz-CH(-CHz-a m- z y -p enoxyacehc CHZ S(O)z acid CH3 ester O-JUZ-NHZ cal3 ~:Hz-LH(-LHz-nnemymai3-pnenoxy- m- z CHz S(O)z acetic CH3 acid ester O-JVz-1VH2 Lti3 ~:riz-aril-~tiz-memym:ri3-u-pnenoxy m- z CHz-S(O)z-CH3acetic acid ester o-~uz-NHz ~ri3 ~riz-~ry-~riz-enemy m- z rsn-v-pnenoxy CHz-S(O)z-CH3acetic acid ester o-SUz-NHz CH3 CHz-CH(-CHz-Yhenoxyacehc m-C;(=NH)NHz acid CHz-S(O)z-CH3 o-SOz-NHz CH3 CHz-CH(-CHz-CI-phenoxy-acetic m- z acid CHz-S(O)z o-SOz NHz CH3 CHz CH(-CHz-H-phenoxy- m- z acetic acid CHz S(O)z o-SOz-NHz CH3 CHz-CH(-CHz-CH3-phenoxy-acetic m- z acid CHz-S(O)2 o- z-NHz CH3 CHz-CH(-CHz-CH3-U-phenoxy-acetic m- z CHz-S(O)z-CH,acid o-SUZ-NHz CH3 CHz-CH(-CHz-n- m- z -p epoxy acetic aci CHz-S(O)2 o-SOZ NHz CH3 z- z- enoxyaceric m- z aci CHz-S(O)z-CH3 o-SOZ-NHz CH3 z- z- -p m- z enoxyacehc aci CHz-S(O)z-CH3 -o-SOZ NHZ CH3 z- z- -p m- z -- enoxyacetic aci CHz-S(O)z-CH3 z- z s z- z- 3 m- z p epoxy-aceric aci CHz-S(O)2 CHs o-z- z LH3 z- z- 3- m- =U z -p enoxy acetic CHz-S(O)z-CH,acid o-5Uz-NHz C:H3 (:Hz-C;H(-C;Hz-Bn-U-phenoxy m-(:(=U)NHz acetic acid CHz-S(O)i CHj O-JVZ-lVri2 3 ~-rii unl-unz-rnenoxyemanol m-l:l=Nrywriz CHz-S(O)z-CH3 O-JUz-lVrlz 3 l:rlz-c.;tll-lalz--p m- z enoxy-a ano CHz-S(O)z CH, O-JUz-Nri2 s z- r -p m- z enoxy-a ano CHz-S(O)z-CH3 o-~uz-Nriz 3 z- z- 3-p m- z enoxy-a ano CHz-S(O)z-CH3 o-~uz-lvHz lal3 Ltlz-fall-l:tlz-cai3-u-pnenoxy-ethanol m-l:l=Nttyvri2 CHz S(O)z-CH3 O-~Vz-lVriz lai3 Lriz-Lril-Lriz-~sn-v-pnenoxy m- z emanol CHz S(O)z-CH3 O-JUZ-iVt12 1x13 1x12-fall-1x12-YnenOXyeman0l m-l:l=u)lVri2 CHz-S(O)z-CH3 o-~uz-lvHz lai3 lalz-lay-tay-1;1-pnenoxyetnanol m- z CHz-S(O)z-CH3 O-JUz-lVtlZ 1;H3 1a12-lall-l;riz-r-prieriOXy-ethanol m-l:l=V)lVtlz CHz-S(U)z-CHj O-~u2-Ntiz 1x13 l:riz l:ril-1;ri2-3-p m-enoxy-a ano CHz-S(O)z-CHj o-JVz tiz 1:H3 l;tlz l;til-1:ri2-1:ri3-V-pnenOXy- m- y N elllanol CHz-S(O)z-CH3 o-JVy-NHZ l.Hg litly-lall-l:riz-13n-V-pnenOXy- m-eLllanol CHZ S(O)z-CHI
z- 2 3 2- z- a m- z y p enoxy-a y CHz-S(O)z-CH3ether O-~uz-lvHz l;ti3 l:rlz-~rll-l:rlz-lvlemyll:l-pnenoxyemyl m-z CHz-S(O)z-CH3ether O-JU2-NriZ 1:H3 l:riz-fall-l:riz-a m-y -p enOXy-a y CHz-S(O)z-CH,ether O-5Uz-NHZ 1:H3 z- z- a m- z y 3-p enoxy-CHz-S(O)z-CH3ethyl ether O-JVZ-NHZ 1.H3 l:riz-loll-1:ri2-lVlelllyll:rig-u-pneriOXy-m-l,l=lVt1)lVriq CHz-S(O)z-CH3ethyl ether O-5V2-NHZ C:H3 l:Hz C;HI-l:riz-lVleitlyl m-t3ri-V-prienOXy CHz-S(O)z-CH3ethyl ether o-~uz-lvtiz 1;H3 z- z- a m- z y enoxye y CHz-S(O)z-CH3ether O-5V2-Nriz C:Hg I:HZ l:Hl-1:H2-lVleUlyl m-l;l=u)lVti2 l:l-pneriOXyelllyl CHz-S(O)z ether O-JUz-lvHz l:rl3 l;rlz-l:rll-l:rlz-lvlemyl m-l,l=u~lvrlz r-pnenoxyewyl CHz-S(O)z-CH3ether o-JVZ tlz 1:H3 l;Hz C;HI-1;H2-lVieTllyl m-l;l=V)lVtlz N 1:ri3-CHz-S(O)z-CH3 phenoxyethyl ether O-JU2-lVHz l;tig l.alz-l;ril-1:ri2-l VleLllyllaig-v-m-l;l=u)lVtlz CHz-S(O)z-CH3 phenoxyethyl ether O-JVy-Ntly Cal3 1:H2-(:ril-1;ri2-l VleLllyl tin-V-m-l:l=V)lVri2 CHz-S(O)z-CH3phenoxyethyl ether o-JUz-lVth laig lalz l:ril-1a12-phenyl m-l.l=lVt1)lVtiz hexane)-O-JUz tiZ 1x13 1:112 l;ril-1:ri2-l:l-pnenyl m-l.l=lVt1)lVri2 lV
hexane)-o-~uz-lvHz l:rl3 l:rlz-l:rll-l;rlz_-p m- z eny hexane)-o-~uz-lvHz l:rl3 l:rlz-l:rll-l:rlz-l:ri3-phenyl m- z hexane)-o-~uz-lvHz lal3 l:rlz l:rll-l;rlz-3_ m- z _p eny hexane)-o-r z r z-v11 U V 11 1 fir' 111111 3 n- -p eny m- z hexane)-o-JVz-Nriz ~ri3 ~riz-aril-~riz-pnenyi m-~l=v)NHz hexane)-O-JUZ Hz 1:H3 l;HZ-l:Hl-l;Hz l:l-pnenyl m-l;l=V)NHz N
hexane)-o-JVZ-NHZ ~ri3 ~riz-aril-~riz-r-pnenyi m-~l=u)NHz hexane)-O-JUz-NHZ 1;H3 l:Hz ;HZ-1;H3-pnenyl m-l;l=U)NHZ
l:Hl-l hexane)-O-JUz-NHZ 1:H3 ~:HZ-liHl-~:HZ-(.;H3-U-prienyl m-Ll=V)NtiZ
hexane)-O-JVz HZ 1:H3 l;Hz-l;Hl-l:Hz tan-u-prieriyl m- z N
hexane)-o-JUz-NHz 1:H3 (:HZ-l;Hl-l:Hz-Arillme p- z hexane)-o-JVz Hz 3 2- Y -am me p- z N
hexane)-O-SUz-NHZ l;Hg l.Hz-C.;HI-1:H2-t'-anllllle p-l;l=NH)lVHz hexane)-O-JV2-NHz 1;H3 l:Hz-l;Hl-1:H2-3-am Ille p- z hexane)-O-JUz-Nriz C.;Hy I;HZ :HZ-3- -am 1ne p-l;Hl-l hexane)-o-5Uz-NHz C:H3 z- 2- n- -am me p- z hexane)-O-5Vz-Nri2 C~H3 l:Hz-l;Hl-C:HZ-m me p- z hexane)-O-JVz Hz C:Hg l;Hz-l:Hl-l:Hy-l;l-anllllle p-N
hexane)-o-~u2 HZ C:H3 l;HZ-l:Hl-~:Hz-r-arillme p- z N
hexane)-O-JUz HZ 1:H3 IIHZ-l;Hl-l:HZ-1:H3-amllrie p- z N
hexane)-O-JUz Hz l:Hj l:Hz-l:Hl-1:H2-1;H3-U-anllme p-N
hexane)-O-JUZ-Nri2 1;H3 l:Hz-l:Hl-l:HZ-II_ -am lrie p-hexane)-O-JUz-NHz 1:H3 l:Hz-l:Hl-l:HZ-eny -amino-car m-OXy 1C
hexane)- acid O-JUZ-Nriz ~H, z- i eny -ammo m- z hexane)- carboxylic acid o-JUz-NHz (:H3 c:Hz-LHl-LHz- r-phenyl-ammo m-~:l=wH)wHz hexane)- carboxylic acid o-JUZ-NHZ 1;H3 C:Hz-C:HI-l:Hz llH3-prieriyl-amlri0m- z hexane)- carboxylic acid o-JUZ-NHZ 1;H3 (:Hz-l:Hl-l;Hz-1:H3-u-prieriyl m- z alrilrio hexane)- carboxylic acid o-5uZ Hz ~:H3 LHZ-LHl-LHZ nn-v-pnenyi ammom-~:l=wri)ivnz N
hexane)- carboxylic acid o-JUz-NHz LH3 ~Hz-~Hl-~Hz- rneny-ammo carnoxyncm-~l=V)mHz hexane)- acid o-~u2 Hz LH3 ~HZ-~Hl-MHz- m-pnenyi-ammo m- z N
hexane)- carboxylic acid o-~uz-NHz ~H, ~HZ-~Hl-~HZ- r-pneny-ammo m-~l=V)mriz hexane)- carboxylic acid o-JUZ-NHZ 1;H3 l:Hz :H2-1:H3-phenyl-ammom-l:l=V)lVHz l;Hl-1 hexane)- carboxylic acid o-JUz Hz 1:H3 C:Hz-l:Hl-~:HZ c:H3 u-pnenyi-ammom-~l=V)wHz N
hexane)- carboxylic acid o-~uz-NHz LH3 uHz-~Hl-uHz- tsn-v-pnenyi-ammom-~l=V)ivHz hexane)- carboxylic acid CHs z- z- a y p ienoxy-aceticm- z J V 1 1Y1 L11 1 1 V~ ivi~t o-t z a z-hexane)- acid ester o-SOz-NHz C:H3 CHz-CH(-CHz- Methyl Cl-phenoxyacehcm-C(=NH)NHz hexane)- acid ester o=SOz-NHz 3 CH2 Hz- Meth~F=phenoxy- m-C(=NH)NHz CH~C acetic hexane)- acid ester O-JUZ-Nriz 1x13 1:ri2-fall-lJriz-itnemyi tai; m-~l=ivn)Nnz pnenoxy-hexane)- acetic acid ester O-~uz-Nriz ~ri3 t:riz-tail-taiz-Metnyi cai3 u-pnenoxy-m-~l=Nti)Ntiz hexane)- acetic acid ester O-JIJZri2 ~-ri3 Lri2-Lril-Lri2-itnemyi tsn-u-pnenoxym-~;l=ivn)ivnz lV
hexane)- acetic acid ester o-SUz-NHz CHj CHz-CH(-CHz- Methyl Yhenoxyacehcm-(:(=U)NHz hexane)- acid ester o-z- z s r z- a y -p enoxyacehcm- z hexane)- acid ester o-SOz-NHz CH3 CHz-CH(-CHz- Methyl r'-phenoxyacehcm-C(=U)NHz hexane)- acid ester O-JVZ-Ntl2 3 ~-tiz-tail-taiz-a Y 3-P enoxy- m- z hexane)- acetic acid ester O-JVZ-Nri2 ~:n, taiz-t:nl-t.nz-a y 3- -p enoxy m- z hexane)- acetic acid ester O-JUy-NHZ s 2- z- a Y n- -p enoxy m- z hexane)- acetic acid ester o~OrNHz CHs CHz-CH(-CHz- Yhenoxyacetic m-C(=NH)NHz acid hexane)-o-z- z CH3 CHz Hz- -p enoxy-acetic m- z CH(-C aci hexane)-o-z- z CH3 CHz-CH(-CHz- -p enoxy- aceticm- z aci hexane)-o-z- z CH3 CHz Hz- 3-p enoxy-aceticm- z CH(-C aci hexane)-o-- z ~ - ~z CH(-CHz- 3- _p enoxy-aceticm- z hexane)- acid o-z- z s z- z- n- -p enoxy aceticm- =NH)NHz aci hexane)-o-2=NHZ CH3 CHz-CH(-CHz- enoxyacehc aci m- z hexane)-o-SOz-NHz CH3 CHz-CH(-CH2 Cl-phenoxyacehc m- z acid hexane)-o-SUz Hz CH3 CHz-CH(-CHz- )~'-phenoxyacehcm-C(=U)NHz N acid hexane)-o-z- Z CH3 CHZ Hz- CH3-phenoxy-aceticm- z CH(-C acid hexane)-o-SOz-NHz CH3 CHz-CH(-CHz- CH3 U-phenoxy m- z acetic hexane)- acid o-SOz-NHz CH3 CHz-CH(-CHz- n- -p enoxy aceticm- z aci hexane)-o-JUz-NHz (:H3 t.;tiz-~atl-Ltlz-enoxye ano m- z hexane)-O-JUZ-NHZ 3 z- z- -p enoxy-a ano m- z hexane)-o-JVz-NHz (:H3 t~tii alz-r-pnenoxy- ethanolm-t:l=ivn)ivnz tail-~
hexane)-o-~u2 Hz cai3 ~ai2 :nz 3-p enoxy-a ano m- z N tail-~
hexane)-o-~Uz-NHz cai3 Ltiz nz- Win,-u-pnenoxy-emanoim- z ~ry-~
hexane)-o-~Uz-Nriz tai3 caiz-t:nl-~nz- rsn-u-pnenoxy m-t.l=ivn)ivnz emanoi hexane)-O-JVZ-Ntl2 1x13 C;tlrl.ril-Lriz-YnenoxyeTnan01 m-l.l=V)tvriz hexane)-o- i- 2 3 z- z- rri=C~2 w.m ua a -p enoxye ano hexane)-O-JVz-NHi C:H3 1;H2-l;H(-l;Hz-r-pnenoxy-emanoim-t,~=U~~riz hexane)-o-SVZ NHz c:Hj ~-Hz-l:H(-l;Hz-3-p enoxy-a ano m- z hexane)-o-~Uz NHz C:H3 l;Hz-(:H(-C:Hz-1:H3 U-prienoxy-m- z etnanot hexane)-o-SUz-NHz c:ri3 l:Hz-(:H(-t,Hz-tin-U-prienoxy- m- z emanoi hexane)-o-SUz-NHz c:H3 c:H2-l:H(-l:Hz-a Y p enoxy-a m-y hexane)- ether o-5Uz-NHz c:H3 l:Hz-c:H(-l;Hz-ivtetnyt la-pnenoxyemyim- z hexane)- ether o-5Vz-Nriz t;H3 t;tt2-c:H(-LHZ-ivtetnyt r-pnenoxy-emytm-hexane)- ether o-5Uz NHZ LH3 c:Hz-l:H(-l:Hzivtetnyt l:rt3-pnenoxy-m-~(=~rt~rrriz hexane)- ethyl ether O-5Uz-NHZ 1;H3 l:rtz-l;H(-1;H2-ivtemyt l:rt3-U-pnenoxy-m-hexane)- ethyl ether o-5Uz-NHZ LH3 l:Hz-l;H(-l:Hz-ivtemyt tsn-u-pnenoxym-~(=lrrt~lrriz hexane)- ethyl ether o-~UZ NHz c:H3 t;Hz-l:H(-latz-ivtemyt rnenoxyetnytm-~;(=U~r~riz hexane)- ether O-5Uz-NHZ c:H3 1:H2-c:H(-I:HZa y -p enoxye m-y hexane)- ether o-~U~ NHz C;H3 c:Hz-(:H(-C:Hz-a y -p enoxye m- z y hexane)- ether o-SUi NHZ C:H3 1;H2-l:H(-(:HZ-a y 3- m- z hexane)- phenoxyethyl ether o-SUZ-NHz C:H3 l;Hz-l:H(-C;HZ-a y 3 - m- z hexane)- phenoxyethyl ether o-5U2-NHz C:H3 l:Hz-l:H(-l:Hz-a y n- m-hexane)- phenoxyethyl ether o-SUz-NHz (_:H3 C:Hz-C:H(-C;Hz-prienyt m- z (HO-phenyl))-o-5Uz-NHz 1:H3 l:Hz-lai(-c.;Hz_-p eny m- z (HO-phenyl))-o-5U2-NHZ C:H3 l:Hz-l:H(-l:Hz-p eriy m-(HO-phenyl))-O-JUz-NHZ C:H3 lain-l:H(-(:Hz~-p eny m-(HO-phenyl))-o-~UZ-Nriz LH3 1:H2-l:H(-l:rtz-l:rt3-U-pnenyt m-(HO-phenyl))-o-~Uz-NHz C;H3 t;Hz-l:H(-l:Hz-tin-u-pnenyt m- z (HO-phenyl))-o-5Uz-NHz C:H3 C:Hz-l:H(-C:Hz-pnenyt m-l:(=U~~ri2 (HO-phenyl))-o-5Uz-NHz t;H3 C:HZ-l:H(-l:Hzla-pnenyl m-l:(=U)mriz (HO-phenyl))-o-5Uz NHz c:H3 t;Hz-l:H(-l;Hz-r-pnenyt m- z (HO-phenyl))-O-5V2-NHZ (:H3 C;HZ-C.;H(-1;H2-3-p eriy m-(HO-phenyl))-O-5U2-NHz C:H3 C:tiz l;H(-1:H2-3- _p eny m-(HO-phenyl))-o-5Uz-Nriz c:H3 2 z- n- -p eny m- z (HO-phenyl))-o-JUZ-NHz 1;H3 z- 2- m me p-(HO-phenyl))-O-JUZ-NHy (:H3 l:riy-l~tl(-1x12_-an11I1e p-(HO-phenyl))-o-- z ~3 z- z_ _~ p- z .... ,_,~~~-,...me (HO-phenyl))-O-JUz-Nriz ~ri3 ~riz-aril-~riz~aij-amime p-~l=Nti~Nttz (HO-phenyl))-o-~uz-Nriz ~ri3 ~riz-aril-~ri2~ri3-u-amime p-~l=NryNriz (HO-phenyl))-o-~uz-Nriz ~ri3 ~riz-~:ril-~riz-nn-u-amime p-~;l=NryNriz (HO-phenyl))-o-~uz-Ntiz ~:ri3 Lr~z-tall-~a~z-Amime p- z (HO-phenyl))-o-z- z s z- z- -am p- z me (HO-phenyl))-o-~uz-Nriz ~ri3 ~riz-aril-~riz-r-amime p-~;l=u)Nrlz (HO-phenyl))-O-JV2-NHZ 1:H3 Z- 2- 3-and p- y me (HO-phenyl))-O-JVZ-Nriz ~;ti, ~riz-aril-t,rlz-~:ri3-v-amime p-~;l=u~Nnz (HO-phenyl))-O-JVZ-NHZ 1;H3 lalz-fall-l;HztSn-V-amlme p-l:l=V)Nriz (HO-phenyl))-O-~uz-NHz ~;H, Lriz-Lril-Lnz-rneny-ammo-carooxync m-t,l=NryNriz (HO-phenyl))-acid o-~uz-NHz ~aij Ltiz-pail-Ltiz~a-rnenyi-ammo m-~l=NryNriz (HO-phenyl))-carboxylic acid O-JUZ-Nriz ~:H3 ~aizway-Lriz-r-pnenyi-ammo m- z (HO-phenyl))-carboxylic acid o-~uz-Ntlz ~;t13 ~tiz-~;til-~tiz-~;ri3-pneny-ammo m-~l=NriJmriz (HO-phenyl))-carboxylic acid o-~u2 tiz ~:H3 tJHZ-tail-LHz-~;t13-u-pnenyi m-Ll=NryNtiz N ammo (HO-phenyl))-carboxylic acid o-JUZ-Nriz ~;H, Lriz-pail-Ltiz-n_ m- z _p eny ammo (HO-phenyl))-carboxylic acid O-JUz-Nriz ~ai3 ~riz-~:ril-~tiz-eny m- z -ammo car oxy is (HO-phenyl))-acid o-~uz-NHz ~ti3 ~riz-aril-~riz-m-pnenyi-ammo m- z (HO-phenyl))-carboxylic acid o-~Uz-Nri2 ~;ti3 ~tiz-~;til-~;ttz_-p m- z eny -ammo (HO-phenyl))-carboxylic acid o-JUZ-Nri2 3 ~.aiz-pail-t,ttz-3-p m- z eny -ammo (HO-phenyl))-carboxylic acid O-JUZ HZ 1:H3 1;H2-lJtil-l;riy-1a13-V-pneriyl-ammo m-N
(HO-phenyl))-carboxylic acid O-JUZ-Ntl2 Lti3 MHz-~;ttl-~;Hz-tsn-u-pnenyi-ammo m-~l=u~Nriz (HO-phenyl))-carboxylic acid o-SOz-NHz CH3 C;Hz-(:H(-CHIa y m- z p enoxy-acetic (HO-phenyl))-acid ester o-SOZ Hz 3 C;Hz (:H(-(:Hz-a y m- z N -p enoxyacehc (HO-phenyl))-acid ester o-SUZ Hz C;H3 C;Hz-C;H(-(:Hz-Methyl m-(:(=NH)NHz N r-phenoxy-acetic (HO-phenyl))-acid ester o-~uz-Ntiz trtij ~:riz-~:ril-~riz-nnemyi m-Ll=1V
~ri3-pnenoxy- ri)1V riz (HO-phenyl))-acetic acid ester O-JUZ-NHZ ~ri3 ~riz-aril-~rizenemy m-~l=NryNriz ~ri3-u-pnenoxy-(HO-phenyl))-acetic acid ester o-~uz-Ntiz ~;ry :riz-~:ril-~riz-enemy m-~:l=NryNriz nn-u-pnenoxy (HO-phenyl))-acetic acid ester o-SOz-NHz CH3 (:Hz-C;H(-(:Hz-Methyl m-C;(=U)NHz Yhenoxyacehc (HO-phenyl))-acid ester o-SUz-NHz LH3 C;Hz-(:H(-(:Hz-Methyl m-(:(=U)NHz (:1-phenoxyacehc (HO-phenyl))-acid ester o-SUz-NHz C;H3 C:Hz-C:H(-C:Hz-a y m-C;(=U)NHz -p enoxyacetlc (HO-phenyl))-acid ester -o- z- z s z- r a Y 3 P epoxy= m-C(=O)NHz (HO-phenyl))-acetic acid ester O-~uz-Nriz Sri, ~riz-aril-~riz-Metnym;ti3-v-pnenoxym-~,l=~)mriz (HO-phenyl))-acetic acid ester O-JVZ-NHy 3 1:ri2-fall-Calz-Mettlyi tSri-V-pnenOXym-l;l=V)lVri2 (HO-phenyl))-acetic acid ester o-SOz-NHz CH3 CHz-CH(-CHz-Yhenoxyacehc m-(:(=NH)NHz acid (HO-phenyl))-o-SOZ NHz CH3 CHz-CH(-CHZCl-phenoxy-aceticm-(:(=NH)NHz acid (HO-phenyl))-o-SOz NHz CH3 CHz-CH(-CHz-r~-phenoxy- aceticm-C(=NH)NHz acid (HO-phenyl))-o-SOZ NHz CH3 CHz-CH(-CHz-3-p epoxy-aceticm- z aci (HO-phenyl))-o-SOz-NHz CH3 CHz-CH(-CHz-3 -p epoxy-aceticm- z (HO-phenyl))-acid o-SOz-NHz CH3 CHz-CH(-CHz-n- -p epoxy aceticm- z aci (HO-phenyl))-o-SOz-NHz CH; Z z- enoxyacehc aci m- z (HO-phenyl))-o- 2 2 3 Z- z- -p enoxyaceric m- z aci (HO-phenyl))-o-~z-NHz CH3 CHz-CH(-CHzr'-phenoxyaceticm-C;(=U)NHz acid (HO-phenyl))-o-Suez-PHz CH3 CHz-CH(-CHZ5-p epoxy-aceticm- z aci (HO-phenyl))-o-~ CH3 CHz-CH(-CHz-3- -p epoxy aceticm- z (HO-phenyl))-acid o- z- z CH3 CHz-CH(-CHz-Bn-U-phenoxy m- z acetic acid (HO-phenyl))-o-JUz NHz lai3 Lrir~-ril-Lrirrnenoxyemanoi m- z (HO-phenyl))-O-JUz NHZ lal; 1:ri2-fail-l;riz-m-pnenoxy-emanoim-~l=ivri)ivriz (HO-phenyl))-o-1u2-NHZ Lti3 Ltiz ~ty-~ry-r-pnenoxy- emanoim-~l=ivri)ivriz (HO-phenyl))-o-5uz NHz t;ti3 ~tiz-~til-Ltiz~ri3-pnenoxy-emanoim-~l=lrri)ivriz (HO-phenyl))-o-~uz Ntiz Lti, ~ry-~ry-~riz-~ri3-~-Pnenoxy-emanoim- z (HO-phenyl))-O-~Uz-Nriz Lti, ~aiz-pail-~aiz-tsn-u-pnenoxy m- z emanoi (HO-phenyl))-O-JU2-NHZ 1:ri3 1;ri2-fall-l:riz-YrieriOXyeman0l m-(HO-phenyl))-O-JU2 NHZ 1;ri3 z- z- -p erioxye ano m-(HO-phenyl))-O-JUZ-Ntiz s 2- r -p epoxy-a ano m- z (HO-phenyl))-o-~u2 NHz cai3 ~aizwailwaiz-3-p epoxy-a ano m- z (HO-phenyl))-o-5uz NHz cai3 ~aizw:ril-~atz-t_ai3-u-pnenoxy-m- z emanoi (HO-phenyl))-O-JV2-NHZ cai, ~;tiz-trtil-~aiz-n_ -p epoxy- m- z a ano (HO-phenyl))-O-~Uz-Nriz ~ri3 ~rizw;ril-~riz-iviemyi pnenoxy-ewyim-~l=ivri)ivriz (HO-phenyl))-ether o-~uZ ivtiz ~ti3 ~rizw:ril-~riz-iviemyi ~i-pnenoxyemyim-~l=ivri)ivriz (HO-phenyl))-ether o-~uz-NHz Ltij caiz-~til-c.aiz-iviemyi r-pnenoxy-einyim-~l=ivri)ivriz (HO-phenyl))-ether o-~uz ivriz Ltij ~aiz-~:ril-~tiz-iviemyi t,ri3 m-l,l=lvtl)LVri2 pnenoxy-(HO-phenyl))-ethyl ether CHs a m-C(=NH)NHz w a~ aa v.m a..ay-w.aay o-z- z z- z- s--phenoxy-ava ua a ~aa v (HO-phenyl))-ethyl ether o-JUz tiz l.ris l:riz-~r1(-c:rtz-Metnyt m- z N tin-V-pnenoxy (HO-phenyl))-ethyl ether o-5uz-Ntiz kris laiz-lay-caiz-Metny m-t;(=l)Nriz rnenoxyemy (HO-phenyl))-ether o-5Vz-Nriz cats caiz-Lti(-caiz-nnemyi m- z la-pnenoxyetnyi (HO-phenyl))-ether o-JUz-NHz 1:ri3 l:riz l;tl(-l:riz-Mettlyl m-l:(=V)lVriz r-pnenOXyelllyl (HO-phenyl))-ether O-JVz-Nriz lai3 l:rlz-t_;tt(-laiz-a m- z Y
(HO-phenyl))- phenoxyethyl ether O-JUz-Nriz 1jt13 t_;tiz-lal(-l:riz- MeiClyll;rij-V-m- z (HO-phenyl))- phenoxyethyl ether O-JVZ-1Vt12 1.r13 l.rlz-lal(-lalz- Memyl tin-V- m-l,~=V)lVrlz (HO-phenyl))-phenoxyethyl ether o-auz-Nriz kris laiz-lai(-laiz-pnenyi m-t;(=rrri)wriz (Cl-phenyl))-O-JVz-Nriz l;tis laiz-~;ti(-l:tiz-la-pneny m-~:~=~ri)Nriz (Cl-phenyl))-o-JVz-Ntiz lass l:riz-~r1(-l:riz--p m- z eny (Cl-phenyl))-O-JUz-Nriz cats la~z-l:rt(-~;t~z-s-p m- z eny (Cl-phenyl))-o-JUz-Nriz 3 z- z- s- m- z -p eny (Cl-phenyl))-O-JVz-Nriz lass t;ti2lai(-laiztsn-u-pnenyi m-~:~=rrri)ivriz (Cl-phenyl))-o-SVz-Nriz cats z- z- p m- z eny (Cl-phenyl))-o-~u2lVtiz lass z- z- -p m- z eny (Cl-phenyl))-o-5u21Vriz Cats z- z- -p m- z eny (Cl-phenyl))-o-JUz-Nriz c:ris l:riz-pry-l:riz-~ri3-pnenyi m-~~=~)mriz (Cl-phenyl))-O-JVz-Ntiz cats laiz-lay-laizl:ryv-pneny m-~.~=v)mriz (Cl-phenyl))-o-JUz tiz lass l:rlz la1(-l:rlz-rsn-u-pnenyi m- z N
(Cl-phenyl))-O-~Vz-NHz 1x13 Calz lal(-l;tlz-Anllme p-~;~=lVt1)iVrlz (Cl-phenyl))-o-JVz-Ntiz Ltis caiz l:ry-l:nz-la-amine p-1:(=~ri)~riz (Cl-phenyl))-O-~VZ t12 lal3 (a12-lal(-laiz-r-amine p-1:~=~ri)rrriz (Cl-phenyl))-o-~uz-lVriz l:ns l:riz-lat(-lJttz-,-am p- z me (Cl-phenyl))-O-JUz-lVriz 1;ri3 1:ri2-l:rl(-l:rlz1;r13-v-arillllle p- z (Cl-phenyl))-O-z z s z- z- n- p-l.~=lVr1)lVrlz -ant me (Cl-phenyl))-o-~uz-lVriz 1x13 lalz-la1(-laiz-Amllne p-1.~=V)lVrlz (Cl-phenyl))-o-~Vz-Nriz a z- z- -am p- z 1rie (Cl-phenyl))-O-JUz-IVHz lalg l;tlz-l;tl(-1:ri2-r-amine p-~:~=~)mriz (Cl-phenyl))-o-JUz-Nriz 1;t13 l:rlz-1:r1(-t;rlz-3-am p- z 1rie (Cl-phenyl))-O-JVz-lVriz 3 2 Y s- p- z -am me (Cl-phenyl))-o- z- z CH3 z- z- n-.... ....~-,_,~~-am me .~
(Cl-phenyl))-O-JVZ-NHZ 1;ri3 1:ri2-fail-1;H2-rneriyl-ammo-CarbOXyllC m-l;l=Ntl)Ntl2 (Cl-phenyl))-acid o-~uz NHZ 3 Lri2-Lril-L'ri2-~a-rnenyi-ammo m- z (Cl-phenyl))-carboxylic acid o-~uz NHZ ~ri3 ~:riz-~;ril-~:riz--p m- z eny -ammo (Cl-phenyl))-carboxylic acid O-JUZ-NHZ Lti3 Ltiz-~;Hl-t;HZ-3-p m- z ieny -ammo (Cl-phenyl))-carboxylic acid o-~uz-NHz Lti3 taiz-pail-~;ttz-cai,-u-pnenyi m- z ammo (Cl-phenyl))-carboxylic acid o-~uz-Ntiz Sri, ~riz-aril-~rizn- m- z -p eny ammo (Cl-phenyl))-carboxylic acid o-~uz-NHz uri, ~riz-~ril-unz-rneny-ammo m-~l=u)wriz carnoxyuc (Cl-phenyl))-acid o-JUZ-Nri2 Sri, ~riz-~ry-~riz-~i-pneny-ammo m- z (CI-phenyl))-carboxylic acid O-JUZ-NHZ ~-ri3 ~riz-~ril-~nz-r-pnenyi-ammo m- z (Cl-phenyl))-carboxylic acid O-JUZ-NY12 Lri3 ~-ri2-~-ril-~-ri2-~-ris-pneny-ammo m-~~=u)mriz (Cl-phenyl))-carboxylic acid o-JVZ-NHZ lal3 1;t12-l;tll-l.:riz-l:rig-V-pneriyl-ammo m-l:l=lJ)Nrl2 (Cl-phenyl))-carboxylic acid O-JUZ-Nri2 uri3 utiz-aril-~riz-nn-u-pnenyi-ammo m-~l=~)wriz (Cl-phenyl))-carboxylic acid o-SOz-NHz CH3 CHz-CH(-CHz-Methyl m-(:(=NH)NHz phenoxy-acetic (Cl-phenyl))-acid ester o-SOz-NHz CH3 CHz-CH(-CHZMethyl m- z Cl-phenoxyacehc (Cl-phenyl))-acid ester o-SOz-NHz CH3 CHz-CH(-CHZa m- z y -p epoxy-acetic (Cl-phenyl))-acid ester O-JVZ-Ntl2 c:H3 r z- a m- z y j-p epoxy-(Cl-phenyl))-acetic acid ester o-~uz-NHz c:H, uriz-aril-uriz-Memyi m-~~=wri)wriz ~ri3-u-pnenoxy-(Cl-phenyl))-acetic acid ester o-JVZ-NH2 C.:H3 1;H2-l:ril-lal2-Memyl m-tSri-V-pneriOXy (Cl-phenyl))-acetic acid ester o-SOz-NHz CH3 CHz-CH(-CHZMethyl m- z Yhenoxyacehc (Cl-phenyl))-acid ester o-SOz-NHz CH3 CHz-CH(-CHz-Methyl m- z Cl-phenoxyacehc (Cl-phenyl))-acid ester o-SOz-NHz CH3 CHz CH(-CHz-Methyl m- z l-phenoxyacehc (Cl-phenyl))-acid ester O-JUZ-Nri2 ~H, ~riz-aril-~riz-Memy m-~l=~)mriz ~rypnenoxy-(Cl-phenyl))-acetic acid ester O-~Vz-NHz ~H3 ~riz-aril-~riz-enemy m- z ~ryu-pnenoxy (Cl-phenyl))-acetic acid ester O-JVz NHz l;rl3 (~H2-l:Hl-1;H2-Meinyl m-l:l=u)Ntl2 tin-u-prienOXy (Cl-phenyl))-acetic acid ester o-SOZ NHz CH3 CHZ CH(-CHz-Yhenoxyacehc m-C(=NH)NHz acid (Cl-phenyl))-o- Oz-NHz CH3 CHZ CH(-CHz-Cl-phenoxy-acetic m-C(=NH)NHz acid (Cl-phenyl))-o-SOz-NHz CH3 CHz-CH(-CHIJ'-phenoxy- m- z acetic acid (Cl-phenyl))-o-SOz-NHz CH3 CHz-CH(-CHzCH3-phenoxy-acetic m- z acid (Cl-phenyl))-o-SOz-NHz CH3 CHz-CH(-CHz-CH3-U-phenoxy-acetic m- z (Cl-phenyl))-acid o-SOz-NHz 3 z- r n- m- z -p epoxy acetic aci (Cl-phenyl))-o-SO ~ CH3 z- z- enoxyacehc m- z aci (Cl-phenyl))-o-JUz-NHz c:H3 C:Hz-(:H(-(:Hz-C:1-phenoxyacehc m-(:(=U)NHz acid (Cl-phenyl))-o-~Uz-NHz C:H3 t:Hz-(:H(-C:Hz-r-phenoxyacehc m-(:(=U)NHz acid (Cl-phenyl))-o-SUz-NHz (:H3 (:Hz-(:H(-C;Hz-C:H3-phenoxy-acehc m-(:(=U)NHz acid (Cl-phenyl))-o-SUz-NHz C:H3 C:Hz-C;H(-(:Hz-C;H3-U-phenoxy m-(:(=U)NHz acehc (Cl-phenyl))-acid o-SUz-NHz 3 z- z- n- m- z -p epoxy acehc aci (Cl-phenyl))-O-JUz-wriz 3 z- z- enoxye m- z ano (Cl-phenyl))-o-~uz-wnz ~-ria ~-nz-~ril-~-riz-~-1-pnenoxy-emanoi m-t:l=mnyvnz (Cl-phenyl))-o-~uz-Ntiz 1:n3 z- z -p m- z epoxy-a ano (Cl-phenyl))-o-~uz-Ntiz t.;n3 ~;nz t:nl-~:nz-~:n3-pnenoxy-emanoi m-t.l=ivnyvnz (Cl-phenyl))-o-~uz-Ntiz t.n3 ~:nz-~:nl-t:nz-3- m- z -p epoxy-a ano (Cl-phenyl))-O-JUz-Nriz ~:ri3 Z z- n- m- z -p epoxy a ano (Cl-phenyl))-O-JVz-Nriz lalg l:riz-fall-lalz-rnenoxyemanoi m-~l=u)~nz (Cl-phenyl))-O-JIJz-Nriz t:n3 ~nz-~nl-t:nz~a-pnenoxyemanoi m- z (Cl-phenyl))-o-Jll2ty :n3 ~:rir~-nl-Lnz-r-pnenoxy-emanoi m-t:l=uyvnz N
(Cl-phenyl))-o-~uz-Ntiz uti3 unz-~nl-unz-un3 m-ul=u~wnz pnenoxy-emanoi (Cl-phenyl))-o-~uz-Nnz t:n3 unz-~nlw:ni~;n3-u-pnenoxy- m- z emanoi (Cl-phenyl))-o-Jl)2tlz Lri3 L'ri2-L'ril-L'ri2-~n-u-pnenoxy- m-t.l=uyvnz N emanoi (Cl-phenyl))-O-~uz-Nriz cai3 ~riz-~nl-~riz-a m- z Y
P
epoxy-a y (Cl-phenyl))-ether o-aVz-Nriz t:ti3 z- z- a m- z y -p enoxye y (Cl-phenyl))-ether o-~u2 Hz s z- z- a m- z N y -p epoxy-a y (Cl-phenyl))-ether o-~Uz-Nriz cai3 taiz-t:nl-t:nz-nnemyi m-t.l=wn~wnz t:n3-pnenoxy-(Cl-phenyl))-ethyl ether o-~u2 Hz t:n3 t:nz-~nl-~nznnecnyi m- z N t:n3-u-pnenoxy-(Cl-phenyl))-ethyl ether o-5uz-Ntiz tai3 t:nz-~nl-t:nza m- z y n--p epoxy (Cl-phenyl))-ethyl ether o-~Uz-Nri2 tai3 t:nz-t:nl-t:nz-nnemyi m- z rnenoxyewyi (Cl-phenyl))-ether o-Jllz-Nri2 tai3 c:nz-trnl-Lnz-Metnym-i-pnenoxyemyi m- z (Cl-phenyl))-ether O-~Uz-Ntiz ~ti, ~nz-~nl-~nz-Memyi m- z r-pnenoxyemyi (Cl-phenyl))-ether O-JUz-Ntiz 1x13 l;tlz-lail-lalz-lVlelllyll.n3- m-l.l=lJ)lVnz (Cl-phenyl))- phenoxyethyl ether O-JUz-Nriz 1:ri3 l:riz-fail-l:riz- MeTriyll:ri3 m-l:l=lJ)lVriz V-(Cl-phenyl))- phenoxyethyl ether o-~uz-Nttz tJtt3 ~;ttz t:nl-t:nz- Memyi tsn-u- m-t.l=a yvnz (Cl-phenyl))-phenoxyethyl ether o-~uz-Nnz lat3 ~;tti tall-tatz-phenyl m-t:l=tvttyvnz ~z)-o-r z s z- z- -P enY m-~:l=Nri)mHz ~2)-o-z- z z- z_ -p eny m-C(=NF~NHz v11 1- 11 1 NHz)_ -o-z- z s z- z_ 3_p eny m2 v11 11 1 ~z) -o-z- z s z- z- m-v11 v 11 1 v 1.11)1.11 s- -P eny NHz)_ 2- 2 m-C(=NH)N
v11 v11 v11 L V 11 1 3 v11~- 2- n- -p eny NHz)_ O-JUz-Nriz 1:H3 l:HZ-l:H(-l:Hz-pnenyl m- z ~z)-O-JUz-NHZ 1:H3 ~HZ-~;Hl-~;HZ m-pnenyi m- z NHz)_ O-~uz-NHz LH, MHz-LH(-MHz- r-pnenyi m- z ~z)_ O-JUZ-Nriz 1:H3 Z z- 3-P enY m- z ~z)-o-z z a z- z- s- -P eny m-C~=0)~z ~z)_ o-JUZ-NHz C;H3 i z- n- -p eny m- z NHz)-o-JUz Hz 3 Z- z m me p- z N
~z)-O-JUZ-NHz 1:H3 1;H2-l:H(-1:H2--an11I1e p-~z)-O-JUz-NHz 1:H3 l:HZ-l:H(-1:H2--ari11I1e p-~z)-O-5U2-NHz 1;H3 l;Hz-(:H(-1:H2-3-am me p-~z)-O-5V2-NHz 1:H3 C;Hz-(:H(-1:H2-3- -aril me p-~z)-O-JUZ Hz 1:H3 l:HZ-l:H(-lalz-t5n-u-anllme p- z N
~2)-o-~Vz-Nriz 1;H3 l;Hz-C:H(-l:Hz-Amllrie p-NHz)_ o-JUz-NHZ 1:H3 l:Hz-C:H(-1:H2-l;l-anllme p- z ~z)-O-aUz-NHZ 1:H3 I:HZ-lai(-1:r12--am me p-~z)-O-JVz Hz (:H3 l:Hz-l:H(-l.HZ-g-am me p- z N
~z)-o-z- z s z- z- 3- -ant me p- z ~2)-O-1Uz-NHZ 1;H3 2- z- n- -am me p- z NHz)-o-JUz Hz 1:H3 r z eny -ammo-car m- z N oxy lc NHz)- acid o-SUz Hz 1:H3 LHz-~;H(-LHZ eny -ammo m- z N
NHz)- carboxylic acid o-JUZ-Nriz ~:H3 ~HZ-~ry-~ty- r-pnenyi-ammo m-~l=mryvnz NHz)- carboxylic acid o-JUZ HZ 1:H3 (:Hz-l:H(-l:Hz-3-p eny -ammo m-N
NHz)- carboxylic acid O-JUZ-NHz 1:H3 l:HZ-l;H(-1:H2-l;Hj U-pnenyl m-l;(=1vH)lvHz ammo NHz)- carboxylic acid o-~uz-NHz ~;H3 LHZ-LH(-~riz nn-u-pnenyi ammom-~:l=mHyvHz NHz)- carboxylic acid O-JVZ Hz 1:H3 l:Hz-l:H(-1;H2-rneny-ammo carnoxyncm-~(=u~NHz N
NHz)- acid o-~uz-NHz ~:H3 MHz-~Hl-~riz-m-pneny-ammo m-~l=m~wriz NHz)- carboxylic acid 0-z- 2 3 2 2- -P eny -ammo m-~~=v~wtiz NHz)- carboxylic acid o-z- x s z- z ~.. .. . ..~ .~,...
3-P enY -~o m- z NHz)- carboxylic acid s r r m-C(=O)NHz U V 11 v11 V 11 1 o-1. z 3- -p eny -ammo z-NHz)- carboxylic acid 0-z- 2 3 2- z- n- -p eny, -ammom-C(=O)NHz NHz)- carboxylic acid o-OZ-NHz CH, CHz-CH(-CHI Methyl phenoxy-aceticm-C(=NH)NHz NHz)- acid ester z-~z 3 z- z- a y -p enoxyacehcm- z J
o-NHz)- acid ester o-r z 3 z- z- a y -p enoXy- m-C(=NH)NHz acetic NHz)- acid ester o-z- z s z- z' a Y s-P epoxy- m- z NHz)- acetic acid ester o-z- z s z- z- m-C(=NH)NHz 1v1 u1 a Yl s- -P epoxy--NHz)- acetic acid ester --o-z- z m - r a Y n- -p epoxy in_C(=NH)NH2 NHz)- acetic acid ester o-SOz-NHz CH3 CHz-CH(-CHz- Methyl Phenoxyacehcm-C(=U)NHz NHz)- acid ester o-2-NHz CH3 CHz-CH(-CHz- Methyl C1-phenoxyacehcm- z NHz)- acid ester o-z- z - CHj CHz-CH(-CHz- Methyl F-phenoxyacehcm- z NHz)- acid ester o-SUz-NHz LH3 ~tiz-l;ti(-caiz-ivietnymrti3-pnenoxy-m- z NHz)- acetic acid ester o-5Vz-NHz c:H3 z- i a Y 3- -P epoxy m- z NHz)- acetic acid ester o-z- 2 3 2- z- m-C(=O)NHz 1v1 ua 11r a y n-O-phenoxy NHz)- acetic acid ester - -o-z- z s z- z- enoxyacehc aci iim-C(=NH)NHz ~z)-o-SOz-NHz CH3 z- r -p epoxy-acetic m- z aci ~z)-o-z ~- CH3 z- z_ -p epoxy- aceticm- z aci ~z)-o-z- z - CH3 CHz-CH(-CHz- 3-p epoxy-aceticm- z aci ~z)-o-z- z j CHz-CH(-CHZ CH3-U-phenoxy-aceticm- z NHz)- acid o-z- z CH3 CHz CHZ Bn-U-phenoxy m- z CH(- acetic acid ~z)--o-z- z 3 z- z- enoxyacehc aci m- _ ~NHz NHz)_ -o-z- z s z- z- -p enoxyacehc m-C(=O)NHz acid NHz)_ o-z-NHz CH3 CHz-CH(-CHz- -p enoxyacehc m- z aci ~z)-o-z-NHz 3 z- z- 3-p epoxy-aceticm- z aci ~z)-o-z-NH2 z- z- 3 -p epoxy aceticm- z J V 1i11 NHz)- acid o-r z s z- z- n- -p epoxy aceticm=C~ O)NHz aci ~z)-o-JVz-Nriz ~;t13 z- r enoxye ano m- z ~z)-O-JUZ-1VHZ lai3 Z- Z- -p epoxy-a ano m-~2)-O-JVZ-lVriz ~ai3 z- z- -p epoxy- a ano m- z ~z)-o- z- z- 3-p m- z ,~ .. ,... enoxy-et ., z s ano z-NHz)_ -o-SOz-NHZ CHI CHz - 3- m- z CH( z- -p enoxy-a ano ~z)-o-~uz-wriz 3 ~riz-~ry-~riznn-u-pnenoxy m-ul=ivti)Ntiz emanoi ~z)-o-~uz-t~ttz 3 ~-riz-~-ril-~-riz-YnenOXyeTnan01 m-l;l=V)Ntl2 ~z)-o-z- z , z- z -p m-~:l=u)~tiz enoxye ano NHz)_ - -o=SO ~ ~3 ~ Z _p m- z ~...~ -...~enoxy-a ano NHz)_ o-z- z 3 z- z- ,-p m-~:l=u)~tiz enoxy-a ano NHz)_ ~ Oz-~z s z- z- 3 m- z -p enoxy-a ano ~z)-o-z- z 3 z- z- n- m- z -p enoxy-a ano ~z)--~ ~ z- a m- z Y
p enoxy-a y NHz)- ether O-JUZ-1Vt12 1.;t13 1.t12-l.tll-l;ti2-enemy m-~:l=mri)r~riz m-pnenoxyemyi NHz)- ether o-~uz-wriz ~ri3 ~riz-aril-~:riz-nnemyi m-ul=Nti)ivtiz r-pnenoxy-emyi NHz)- ether o-au2 riz ~ri3 ~riz-aril-~riz-enemy m-ul=~ri)~riz ~ ~ri3-pnenoxy-NHz)- ethyl ether O-JUZ-wriz ~ri3 ~riz-aril-~riz-enemy m-~:l=~ri)Nriz ~ri3 u-pnenoxy-NHz)- ethyl ether O-JU2 riz ~ri3 ~riz-aril-~riz-Meruyi m-ul=Nri)rVriz w rsn-u-pnenoxy NHz)- ethyl ether O-luz riz ~;ti3 ~aiz-~til-~;riz-iviemyi m-~;l=u)~riz ~ rnenoxyemyi NHz)- ether O-JUz riz 3 ~riz-aril-~tiz enemy m-~l=u)~riz r~ m-pnenoxyerxiy NHz)- ether o-z- z 3 r z a m-Ll=u)Nriz Y
-P
enoxye y NHz)- ether o-r z s z- z- a m- z Y
a-NHz)- phenoxyethyl - ether o-~Oz-1~ CH3 z- CHZ a y 3=O- tn-C~z (-NHz)- phenoxyethyl ether o-z- z a z- z- Memyi rsn-u- m-~l=u)~riz NHz)- phenoxyethyl ether This invention also encompasses all pharmaceutically acceptable isomers, salts, hydrates and solvates of the compounds of formulas I, II and III. In addition, the compounds of formulas I, II and III can exist in various isomeric and tautomeric forms, and all such forms are meant to be included in the invention, along with pharmaceutically acceptable salts, hydrates and solvates of such isomers and tautomers.
The compounds of this invention may be isolated as the free acid or base or converted to salts of various inorganic and organic acids and bases. Such salts are within the scope of this invention. Non-toxic and physiologically compatible salts are particularly useful although other less desirable salts may have use in the processes of isolation and purification.
A number of methods are useful for the preparation of the salts described above and are known to those skilled in the art. For example, the free acid or free base form of a compound of one of the formulas above can be reacted with one or more molar equivalents of the desired acid or base in a solvent or solvent mixture in which the salt is insoluble, or in a solvent like water after which the solvent is removed by evaporation, distillation or freeze drying. Alternatively, the free acid or base form of the product may be passed over an ion exchange resin to form the desired salt or one salt form of the product may be converted to another using the same general process.
Prodrug Derivatives of Compounds This invention also encompasses prodrug derivatives of the compounds contained herein. The term "prodrug" refers to a pharmacologically inactive derivative of a parent drug molecule that requires biotransformation, either spontaneous or enzymatic, within the organism to release the active drug.
Prodrugs are variations or derivatives of the compounds of this invention which have groups cleavable under metabolic conditions. Prodrugs become the compounds of the invention which are pharmaceutically active in vivo, when they undergo solvolysis under physiological conditions or undergo enzymatic degradation. Prodrug compounds of this invention may be called single, double, triple etc., depending on the number of biotransformation steps required to release the active drug within the organism, and indicating the number of functionalities present in a precursor-type form. Prodrug forms often offer advantages of solubility, tissue compatibility, or delayed release in the mammalian organism (see, Bundgard, Design of Prodrugs, pp.
Provisional Application No. 60/135,819 filed on May 24, 1999, which is herein incorporated in its entirety by reference.
Field of the Invention This invention relates to novel compounds which are potent and highly selective inhibitors of isolated factor Xa or when assembled in the prothrombinase complex. These compounds show selectivity for factor Xa versus other proteases of the coagulation (e.g. thrombin, fVIIa, fIXa) or the fibrinolytic cascades (e.g.
plasminogen activators, plasmin). In another aspect, the present invention relates to novel monoamidino-containing compounds, their pharmaceutically acceptable salts, and pharmaceutically acceptable compositions thereof which are useful as potent and specific inhibitors of blood coagulation in mammals. In yet another aspect, the invention relates to methods for using these inhibitors as therapeutic agents for disease states in mammals characterized by coagulation disorders.
Background of the Invention Hemostasis, the control of bleeding, occurs by surgical means, or by the physiological properties of vasoconstriction and coagulation. This invention is particularly concerned with blood coagulation and ways in which it assists in maintaining the integrity of mammalian circulation after injury, inflammation, disease, congenital defect, dysfunction or other disruption. Although platelets and blood coagulation are both involved in thrombus formation, certain components of the coagulation cascade are primarily responsible for the amplification or acceleration of the processes involved in platelet aggregation and fibrin deposition.
Thrombin is a key enzyme in the coagulation cascade as well as in hemostasis. Thrombin plays a central role in thrombosis through its ability to catalyze the conversion of fibrinogen into fibrin and through its potent platelet activation activity. Direct or indirect inhibition of thrombin activity has been the focus of a variety of recent anticoagulant strategies as reviewed by Claeson, G., "Synthetic Peptides and Peptidomimetics as Substrates and Inhibitors of Thrombin and Other Proteases in the Blood Coagulation System", Blood Coag. Fibrinol.
5_, 411-436 (1994). Several classes of anticoagulants currently used in the clinic directly or indirectly affect thrombin (i.e. heparins, low-molecular weight heparins, heparin-like compounds and coumarins).
A prothrombinase complex, including Factor Xa (a serine protease, the activated form of its Factor X precursor and a member of the calcium ion binding, gamma carboxyglutamyl (Gla)-containing, vitamin K dependent, blood coagulation glycoprotein family), converts the zymogen prothrombin into the active procoagulant thrombin. Unlike thrombin, which acts on a variety of protein substrates as well as at a specific receptor, factor Xa appears to have a single physiologic substrate, namely prothrombin. Since one molecule of factor Xa may be able to generate up to 138 molecules of thrombin (Elodi et al., Thromb. Res. 1 S, 617-619 (1979)), direct inhibition of factor Xa as a way of indirectly inhibiting the formation of thrombin may be an efficient anticoagulant strategy. Therefore, it has been suggested that compounds which selectively inhibit factor Xa may be useful as in vitro diagnostic agents, or for therapeutic administration in certain thrombotic disorders, see e.g., WO 94/13693.
Polypeptides derived from hematophagous organisms have been reported which are highly potent and specific inhibitors of factor Xa. United States Patent 4,588,587 describes anticoagulant activity in the saliva of the Mexican leech, Haementeria o~cinalis. A principal component of this saliva was shown to be the polypeptide factor Xa inhibitor, antistasin (ATS), by Nutt, E. et al., "The Amino Acid Sequence of Antistasin, a Potent Inhibitor of Factor Xa Reveals a Repeated Internal Structure", J. Biol. Chem., ~, 10162-10167 (1988). Another potent and highly specific inhibitor of Factor Xa, called tick anticoagulant peptide (TAP), has been isolated from the whole body extract of the soft tick Ornithidoros moubata, as reported by Waxman, L., et al., "Tick Anticoagulant Peptide (TAP) is a Novel Inhibitor of Blood Coagulation Factor Xa" Science, 2,~8, 593-596 (1990).
Factor Xa inhibitory compounds which are not large polypeptide-type inhibitors have also been reported including: Tidwell, R.R. et al., "Strategies for Anticoagulation With Synthetic Protease Inhibitors. Xa Inhibitors Versus Thrombin Inhibitors", Thromb. Res., 1~, 339-349 (1980); Turner, A.D. et al., "p-Amidino Esters as Irreversible Inhibitors of Factor IXa and Xa and Thrombin", Biochemistry, 25, 4929-4935 (1986); Hitomi, Y. et al., "Inhibitory Effect of New Synthetic Protease Inhibitor (FUT-175) on the Coagulation System", Haemostasis, ~S, 164-168 (1985); Sturzebecher, J. et al., "Synthetic Inhibitors of Bovine Factor Xa and Thrombin. Comparison of Their Anticoagulant Efficiency", Thromb. Res., ~, 245-252 (1989); Kam, C.M. et al., "Mechanism Based Isocoumarin Inhibitors for Trypsin and Blood Coagulation Serine Proteases: New Anticoagulants", Biochemistry, ~, 2547-2557 (1988); Hauptmann, J. et al., "Comparison of the Anticoagulant and Antithrombotic Effects of Synthetic Thrombin and Factor Xa Inhibitors", Thromb. Haemost., ~~, 220-223 (1990); and the like.
Others have reported Factor Xa inhibitors which are small molecule organic compounds, such as nitrogen containing heterocyclic compounds which have amidino substituent groups, wherein two functional groups of the compounds can bind to Factor Xa at two of its active sites. For example, WO 98/28269 describes pyrazole compounds having a terminal C(=NH)-NHz group; WO 97/21437 describes benzimidazole compounds substituted by a basic radical which are connected to a naththyl group via a straight or branched chain alkylene,-C(=O) or -S(=O)2 bridging group; WO 99/10316 describes compounds having a 4-phenyl-N-alkylamidino-piperidine and 4-phenoxy-N-alkylamidino-piperidine group connected to a 3-amidinophenyl group via a carboxamidealkyleneamino bridge; and EP 798295 describes compounds having a 4-phenoxy-N-alkylamidino-piperidine group connected to an amidinonaphthyl group via a substituted or unsubstituted sulfonamide or carboxamide bridging group.
There exists a need for effective therapeutic agents for the regulation of hemostasis, and for the prevention and treatment of thrombus formation and other pathological processes in the vasculature induced by thrombin such as restenosis and inflammation. In particular, there continues to be a need for compounds which selectively inhibit factor Xa or its precursors. Compounds that have different combinations of bridging groups and functional groups than compounds previously discovered are needed, particularly compounds which selectively or preferentially bind to Factor Xa. Compounds with a higher degree of binding to Factor Xa than to thrombin are desired, especially those compounds having good bioavailability and/or solubility.
Summary! ,of the Invention The present invention relates to novel compounds which inhibit factor Xa, their pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives, and pharmaceutically acceptable compositions thereof which have particular biological properties and are useful as potent and specific inhibitors of blood coagulation in mammals. In another aspect, the invention relates to methods of using these inhibitors as diagnostic reagents or as therapeutic agents for disease states in mammals which have coagulation disorders, such as in the treatment or prevention of any thrombotically mediated acute coronary or cerebrovascular syndrome, any thrombotic syndrome occurring in the venous system, any coagulopathy, and any thrombotic complications associated with extracorporeal circulation or instrumentation, and for the inhibition of coagulation in biological samples.
In certain embodiments, this invention relates to novel compounds which are potent and highly selective inhibitors of isolated factor Xa when assembled in the prothrombinase complex. These compounds show selectivity for factor Xa versus other proteases of the coagulation cascade (e.g. thrombin, etc.) or the fibrinolytic cascade, and are useful as diagnostic reagents as well as antithrombotic agents.
In a preferred embodiment, the present invention provides a compound of the formula I:
A-Y-D-E-G-J-Z-L
wherein:
A is selected from:
(a) C,-C6 alkyl;
(b) C3-Cg-cycloalkyl;
(c) phenyl, which is independently substituted with 0-2 R' substituents;
(d) naphthyl, which is independently ' substituted with 0-2 R' substituents;and (e) a monocyclic or fused bicyclic heterocyclic ring system having from 5 to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R' substituents;
R' is selected from:
Halo, C,~,alkyl, Cz_6alkenyl, Cz_balkynyl, C3_8cycloalkyl, Co~alkylC3_ 8cycloalkyl,-CN, -NOz, (CHz)mNR2R3, SOzNRzR', SOZRz, CF3, ORz, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, C,-C4 alkyl, -CN C,~,alkyl, Cz_6alkenyl, Cz_ balkynyl, C3_$cycloalkyl, Co~alkylC3_gcycloalkyl and -NOz;
Rz and R3 are independently selected from the group consisting of H, C,~,alkyl, Cz_6alkenyl, Cz_6alkynyl, C3_gcycloalkyl, Co~alkylC3_8cycloalkyl, Co~alkylphenyl and Co~alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C,~alkyl, Cz_6alkenyl, Cz_6alkynyl, C3_$cycloalkyl, Co~alkylC3_gcycloalkyl, -CN, and -NOz 1 S m is an integer of 0-2;
Y is a member selected from the group consisting of a direct link, -C(=O)-, -N(R4)-, -C(=O)-N(R4)-, -N(R4)-C(=O)-, -SOz-, -O-, -SOz-N(R4)- and N(R4)-SOz-;
R4 is selected from:
H, C,~alkyl, Cz_6alkenyl, Cz_balkynyl, C3_8cycloalkyl, C~alkylC3_8cycloalkyl, Co~alkylphenyl and C~alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C,~alkyl, Cz_6alkenyl, Cz_6alkynyl, C3_8cycloalkyl, Co~alkylC3_8cycloalkyl, -CN, and -NOz;.
D is a direct link or is a member selected from the group consisting of (a) phenyl, which is independently substituted with 0-2 R'a substituents;
(b) naphthyl, which is independently substituted with 0-2 R'a substituents; and (c) a monocyclic or fused bicyclic heterocyclic ring system having from to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R'a substituents;
S R'a is selected from:
Halo, C,.~alkyl, Cz_6alkenyl, Cz_balkynyl, C3_8cycloalkyl, Co~alkylC3_ 8cycloalkyl, -CN, -NOz, (CHz)mNRzeR'a, SOZNRzaR38, SOZRza, CF3, ORza, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, C,~alkyl, Cz_6alkenyl, Cz_ 6alkynyl, C3_$cycloalkyl, C~alkylC3_$cycloalkyl, -CN and -NOz;
Rze and R3a are independently selected from the group consisting of H, C,~alkyl, Cz_6alkenyl, Cz_6alkynyl, C3_gcycloalkyl, Co~alkylC3_8cycloalkyl, Co~alkylphenyl and C~alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C,~alkyl, Cz_6alkenyl, Cz_6alkynyl, C3_gcycloalkyl, Co~alkylC3_8cycloalkyl, -CN and _NOz ~.
E is a member selected from the group consisting of:
-N(RS)-C(=O)-, -C(=O)-N(RS)-, -N(RS)-C(=O)-N(R6)-, -SOz N(RS)-, -N(RS)-SOz-N(R6)- and -N(RS)-SOz N(R6)-C(=O)-;
RS and R6 are independently selected from:
H, C,~alkyl, Cz_6alkenyl, Cz_6alkynyl, C3_8cycloalkyl, C~alkylC3_$cycloalkyl, Co~alkylphenyl, Co~alkylnaphthyl, C~alkylheteroaryl, C,,~alkylCOOH and C,~alkylCOOC,~alkyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl, naphthyl and heteroaryl moieties may be independently replaced with a member selected from the group consisting of halo, C,~alkyl, Cz_6alkenyl, Cz_6alkynyl, C3_8cycloalkyl, Co~alkylC3_$cycloalkyl, -CN and -NOz;
G is selected from:
_7_ -CR'R$- and -CR'Rga-CR'~RBb-wherein R', Rg, R'a, RBa, R'~ and R8b are independently a member selected from from the group consisting of:
hydrogen, C,~alkyl, Cz_6alkenyl, CZ_6alkynyl, C3_8cycloalkyl, C~alkyl-C3_ S gcycloalkyl, C°~,alkylphenyl, C°~alkylnaphthyl, -OR9,-C°~alkylCOOR9, -C°~alkylC(=O)NR9R'°, -C°.~alkylC(=O)NR9-CHZ-CHZ O-R'°, -Co~alkylC(=O)NR9(-CHZ-CHZ-O-R'°-)2, -N(R9)COR'°, -N(R9)C(=O)R'°, -N(R9)SOZR'°, and a naturally occurring or synthetic amino acid side chain, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C,~alkyl, CZ_6alkenyl, Cz_balkynyl, C3_ 8cycloalkyl, C°~alkyl-C3_8cycloalkyl, -CN and -NO2;
R9 and R'° are independently selected from:
H, C,~alkyl, C°~alkylphenyl and C°~alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C,~alkyl, CZ_6alkenyl, Cz_6alkynyl, C3_$cycloalkyl, C°~alkyl-C3_ 8cycloalkyl, -CN and -NO2, and wherein R9 and R'° taken together can form a 5-8 membered heterocylic ring;
J is a member selected from the group consisting of:
a direct link, -CH(R")- and -CH(R")-CHz ;
R' ' is a member selected from the group consisting of hydrogen, C,~alkyl, CZ_6alkenyl, Cz_6alkynyl, C3_gcycloalkyl, C°~alkyl-C3_ 8cycloalkyl, C°~alkylphenyl, C~alkylnaphthyl, C°-0alkylheterocyclic ring having from 1 to 4 hetero ring atoms selected from the group consisting of N, O and S, CHZCOOC,~alkyl, CHZCOOC,~,alkylphenyl and CHZCOOC,~alkylnaphthyl;
Z is a member selected from the group consisting of:
(a) phenyl, which is independently substituted with 0-2 R'b substituents;
_g_ (b) naphthyl, which is independently substituted with 0-2 R'b substituents; and (c) a monocyclic or fused bicyclic heterocyclic ring system having from S to 10 ring atoms, wherein 1-4 ring atoms of the ring system are S selected from N, O and S, and wherein the ring system may be substituted with 0-2 R'b substituents;
R'b is selected from:
Halo, C,~alkyl, Cz_6alkenyl, Cz_6alkynyl, C,_gcycloalkyl, Co~alkylC3_ $cycloalkyl, -CN, -NOz, NRzbR3b~ SOZNRzbR3b, SOzRzb, CF3, ORzb, O-CHZ
CHz-ORzb, O-CHz-COORzb, N(Rzb)-CHZ CHz ORzb, N(-CHz-CHz ORzb)z, N(Rzb)-C(=O)R3b, N(Rzb)-SOz-R'b, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, C,~alkyl, Cz_balkenyl, Cz_6alkynyl, C3_8cycloalkyl, C~alkylC3_ gcycloalkyl, -CN and -NOz;
Rzb and R3b are independently selected from the group consisting of H, C,~alkyl, Cz_6alkenyl, Cz_6alkynyl, C3_gcycloalkyl, Co~alkylC3_acycloalkyl, _ C~alkylphenyl and Co~alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C,~alkyl, Cz_6alkenyl, Cz_balkynyl, C3_acycloalkyl, Co~alkylC3_gcycloalkyl, -CN and -NOz L is selected from:
$~ _CN~ C(-O)yzR~s~ (Cgz)nWzRi3~ ~(-~12)~12R13' ~12R13' OR'z, -~12~(-~12)~12R13' and NRIZC(=NR'z)-R'3;
R'z and R'3 are independently selected from:
hydrogen, -OR'4, -NR'4R'S, C,~alkyl, Co~alkylphenyl, Co~alkylnaphthyl, COOC,~,alkyl, COO-Co~alkylphenyl and COO-Co~alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C,~alkyl, CZ_6alkenyl, CZ_6alkynyl, C3_8cycloalkyl, Co~alkylC3_gcycloalkyl, -CN, and -NO2;
R'4 and R'S are independently selected from:
H, C,~alkyl, Cz_6alkenyl, CZ_6alkynyl, C3_$cycloallcyl, Co~alkylC3_8cycloalkyl, C~,,alkylphenyl and Co~alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C,~alkyl, Cz_6alkenyl, CZ_6alkynyl, C3_gcycloalkyl, Co~alkylC3_8cycloalkyl, -CN, and -NOZ;
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
In certain aspects of this invention, compounds are provided which are useful as diagnostic reagents. In another aspect, the present invention includes pharmaceutical compositions comprising a pharmaceutically effective amount of the 1 S compounds of this invention and a pharmaceutically acceptable Garner. In yet another aspect, the present invention includes methods comprising using the above compounds and pharmaceutical compositions for preventing or treating disease states characterized by undesired thrombosis or disorders of the blood coagulation process in mammals, or for preventing coagulation in biological samples such as, for example, stored blood products and samples. Optionally, the methods of this invention comprise administering the pharmaceutical composition in combination with an additional therapeutic agent such as an antithrombotic and/or a thrombolytic agent and/or an anticoagulant.
The preferred compounds also include their pharmaceutically acceptable isomers, hydrates, solvates, salts and prodrug derivatives.
Detailed Description of the Invention Definitions In accordance with the present invention and as used herein, the following terms are defined with the following meanings, unless explicitly stated otherwise.
The term "alkenyl" refers to a trivalent straight chain or branched chain unsaturated aliphatic radical. The term "alkinyl" (or "alkynyl") refers to a straight or branched chain aliphatic radical that includes at least two carbons joined by a triple bond. If no number of carbons is specified alkenyl and alkinyl each refer to radicals having from 2-12 carbon atoms.
The term "alkyl" refers to saturated aliphatic groups including straight-chain, branched-chain and cyclic groups having the number of carbon atoms specified, or if no number is specified, having up to 12 carbon atoms. The term "cycloalkyl" as used herein refers to a mono-, bi-, or tricyclic aliphatic ring having 3 to 14 carbon atoms and preferably 3 to 7 carbon atoms.
As used herein, the terms "carbocyclic ring structure " and " C3_,6 carbocyclic mono, bicyclic or tricyclic ring structure" or the like are each intended to mean stable ring structures having only carbon atoms as ring atoms wherein the ring structure is a substituted or unsubstituted member selected from the group consisting of: a stable monocyclic ring which is aromatic ring ("aryl") having six ring atoms; a stable monocyclic non-aromatic ring having from 3 to 7 ring atoms in the ring;
a stable bicyclic ring structure having a total of from 7 to 12 ring atoms in the two rings wherein the bicyclic ring structure is selected from the group consisting of ring structures in which both of the rings are aromatic, ring structures in which one of the rings is aromatic and ring structures in which both of the rings are non-aromatic; and a stable tricyclic ring structure having a total of from 10 to 16 atoms in the three rings wherein the tricyclic ring structure is selected from the group consisting of ring structures in which three of the rings are aromatic, ring structures in which two of the rings are aromatic and ring structures in which three of the rings are non-aromatic. In each case, the non-aromatic rings when present in the monocyclic, bicyclic or tricyclic ring structure may independently be saturated, partially saturated or fully saturated. Examples of such carbocyclic ring structures include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, cyclooctyl, [3.3.0]bicyclooctane, [4.3.0]bicyclononane, [4.4.0]bicyclodecane (decalin), 2.2.2]bicyclooctane, fluorenyl, phenyl, naphthyl, indanyl, adamantyl, or tetrahydronaphthyl (tetralin). Moreover, the ring structures described herein may be attached to one or more indicated pendant groups via any carbon atom which results in a stable structure. The term "substituted" as used in conjunction with carbocyclic ring structures means that hydrogen atoms attached to the ring carbon atoms of ring structures described herein may be substituted by one or more of the substituents indicated for that structure if such substitutions) would result in a stable compound.
The term "aryl" which is included with the term "carbocyclic ring structure"
refers to an unsubstituted or substituted aromatic ring, substituted with one, two or three substituents selected from loweralkoxy, loweralkyl, loweralkylamino, hydroxy, halogen, cyano, hydroxyl, mercapto, vitro, thioalkoxy, carboxaldehyde, carboxyl, carboalkoxy and carboxamide, including but not limited to carbocyclic aryl, heterocyclic aryl, and biaryl groups and the like, all of which may be optionally substituted. Preferred aryl groups include phenyl, halophenyl, loweralkylphenyl, napthyl, biphenyl, phenanthrenyl and naphthacenyl.
The term "arylalkyl" which is included with the term "carbocyclic aryl"
refers to one, two, or three aryl groups having the number of carbon atoms designated, appended to an alkyl group having the number of carbon atoms designated. Suitable arylalkyl groups include, but are not limited to, benzyl, picolyl, 1 S naphthylmethyl, phenethyl, benzyhydryl, trityl, and the like, all of which may be optionally substituted.
As used herein, the term "heterocyclic ring" or "heterocyclic ring system" is intended to mean a substituted or unsubstituted member selected from the group consisting of stable monocyclic ring having from 5-7 members in the ring itself and having from 1 to 4 hetero ring atoms selected from the group consisting of N, O and S; a stable bicyclic ring structure having a total of from 7 to 12 atoms in the two rings wherein at least one of the two rings has from 1 to 4 hetero atoms selected from N, O and S, including bicyclic ring structures wherein any of the described stable monocyclic heterocyclic rings is fused to a hexane or benzene ring; and a stable tricyclic heterocyclic ring structure having a total of from 10 to 16 atoms in the three rings wherein at least one of the three rings has from 1 to 4 hetero atoms selected from the group consisting of N, O and S. Any nitrogen and sulfur atoms present in a heterocyclic ring of such a heterocyclic ring structure may be oxidized.
Unless indicated otherwise the terms "heterocyclic ring" or "heterocyclic ring system" include aromatic rings, as well as non-aromatic rings which can be saturated, partially saturated or fully saturated non-aromatic rings. Also, unless indicated otherwise the term "heterocyclic ring system" includes ring structures wherein all of the rings contain at least one hetero atom as well as structures having less than all of the rings in the ring structure containing at least one hetero atom, for example bicyclic ring structures wherein one ring is a benzene ring and one of the rings has one or more hetero atoms are included within the term "heterocyclic ring systems" as well as bicyclic ring structures wherein each of the two rings has at least one hetero atom. Moreover, the ring structures described herein may be attached to one or more indicated pendant groups via any hetero atom or carbon atom which results in a stable structure. Further, the term "substituted" means that one or more of the hydrogen atoms on the ring carbon atoms) or nitrogen atoms) of the each of the rings in the ring structures described herein may be replaced by one or more of the indicated substituents if such replacements) would result in a stable compound.
Nitrogen atoms in a ring structure may be quaternized, but such compounds are specifically indicated or are included within the term "a pharmaceutically acceptable salt" for a particular compound. When the total number of O and S atoms in a single heterocyclic ring is greater than 1, it is preferred that such atoms not be adjacent to one another. Preferably, there are no more that 1 O or S ring atoms in the same ring of a given heterocyclic ring structure.
Examples of monocylic and bicyclic heterocylic ring systems, in alphabetical order, are acridinyl, azocinyl, benzimidazolyl, benzofuranyl, benzothiofuranyl, benzothiophenyl, benzoxazolyl, benzthiazolyl, benztriazolyl, benztetrazolyl, benzisoxazolyl, benzisothiazolyl, benzimidazalinyl, carbazolyl, 4aH-carbazolyl, carbolinyl, chromanyl, chromenyl, cinnolinyl, decahydroquinolinyl, 2H,6H-1,5,2-dithiazinyl, dihydrofuro[2,3-b]tetrahydrofurarl, furanyl, furazanyl, imidazolidinyl, imidazolinyl, imidazolyl, 1H-indazolyl, indolinyl, indolizinyl, indolyl, 3H-indolyl, isobenzofuranyl, isochromanyl, isoindazolyl, isoindolinyl, isoindolyl, isoquinolinyl (benzimidazolyl), isothiazolyl, isoxazolyl, morpholinyl, naphthyridinyl, octahydroisoquinolinyl, oxadiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, oxazolidinyl, oxazolyl, oxazolidinyl, pyrimidinyl, phenanthridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxathiinyl, phenoxazinyl, phthalazinyl, piperazinyl, piperidinyl, pteridinyl, purinyl, pyranyl, pyrazinyl, pyroazolidinyl, pyrazolinyl, pyrazolyl, pyridazinyl, pryidooxazole, pyridoimidazole, pyridothiazole, pyridinyl, pyridyl, pyrimidinyl, pyrrolidinyl, pyrrolinyl, 2H-pyrrolyl, pyrrolyl, quinazolinyl, quinolinyl, 4H-quinolizinyl, quinoxalinyl, quinuclidinyl, tetrahydrofuranyl, tetrahydroisoquinolinyl, tetrahydroquinolinyl, 6H-1,2,5-thiadazinyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, thianthrenyl, thiazolyl, thienyl, thienothiazolyl, thienooxazolyl, thienoimidazolyl, thiophenyl, triazinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,2,5-triazolyl, 1,3,4-triazolyl and xanthenyl. Preferred heterocyclic ring structures include, but are not limited to, pyridinyl, furanyl, thienyl, pyrrolyl, pyrazolyl, pyrrolidinyl, imidazolyl, indolyl, benzimidazolyl, 1H-indazolyl, oxazolinyl, or isatinoyl. Also included are fused ring and spiro compounds containing, for example, the above heterocylic ring structures.
As used herein the term "aromatic heterocyclic ring system" has essentially the same definition as for the monocyclic and bicyclic ring systems except that at least one ring of the ring system is an aromatic heterocyclic ring or the bicyclic ring has an aromatic or non-aromatic heterocyclic ring fused to an aromatic carbocyclic ring structure.
The terms "halo" or "halogen" as used herein refer to Cl, Br, F or I
substituents. The term "haloalkyl", and the like, refer to an aliphatic carbon radicals having at least one hydrogen atom replaced by a Cl, Br, F or I atom, including mixtures of different halo atoms. Trihaloalkyl includes trifluoromethyl and the like as preferred radicals, for example.
The term "methylene" refers to -CH2-.
The term "pharmaceutically acceptable salts" includes salts of compounds derived from the combination of a compound and an organic or inorganic acid.
These compounds are useful in both free base and salt form. In practice, the use of the salt form amounts to use of the base form; both acid and base addition salts are within the scope of the present invention.
"Pharmaceutically acceptable acid addition salt" refers to salts retaining the biological effectiveness and properties of the free bases and which are not biologically or otherwise undesirable, formed with inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid and the like, and organic acids such as acetic acid, propionic acid, glycolic acid, pyruvic acid, oxalic acid, malefic acid, malonic acid, succinic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, p-toluenesulfonic acid, salicyclic acid and the like.
"Pharmaceutically acceptable base addition salts" include those derived from inorganic bases such as sodium, potassium, lithium, ammonium, calcium, magnesium, iron, zinc, copper, manganese, aluminum salts and the like.
Particularly preferred are the ammonium, potassium, sodium, calcium and magnesium salts.
Salts derived from pharmaceutically acceptable organic nontoxic bases include salts of primary, secondary, and tertiary amines, substituted amines including naturally occurring substituted amines, cyclic amines and basic ion exchange resins, such as isopropylamine, trimethylamine, diethylamine, triethylamine, tripropylamine, ethanolamine, 2-diethylaminoethanol, trimethamine, dicyclohexylamine, lysine, arginine, histidine, caffeine, procaine, hydrabamine, choline, betaine, ethylenediamine, glucosamine, methylglucamine, theobromine, purines, piperizine, piperidine, N-ethylpiperidine, polyamine resins and the like. Particularly preferred organic nontoxic bases are isopropylamine, diethylamine, ethanolamine, trimethamine, dicyclohexylamine, choline, and caffeine.
"Biological property" for the purposes herein means an in vivo effector or antigenic function or activity that is directly or indirectly performed by a compound of this invention that are often shown by in vitro assays. Effector functions include receptor or ligand binding, any enzyme activity or enzyme modulatory activity, any Garner binding activity, any hormonal activity, any activity in promoting or inhibiting adhesion of cells to an extracellular matrix or cell surface molecules, or any structural role. Antigenic functions include possession of an epitope or antigenic site that is capable of reacting with antibodies raised against it.
In the compounds of this invention, carbon atoms bonded to four non-identical substituents are asymmetric. Accordingly, the compounds may exist as diastereoisomers, enantiomers or mixtures thereof. The syntheses described herein may employ racemates, enantiomers or diastereomers as starting materials or intermediates. Diastereomeric products resulting from such syntheses may be separated by chromatographic or crystallization methods, or by other methods known in the art. Likewise, enantiomeric product mixtures may be separated using the same techniques or by other methods known in the art. Each of the asymmetric carbon atoms, when present in the compounds of this invention, may be in one of two configurations (R or S) and both are within the scope of the present invention.
Preferred Embodiments In a preferred embodiment, the present invention provides a compound according to the formula I:
A-Y-D-E-G-J-Z-L
wherein:
A is selected from:
(a) C,-C6 alkyl;
(b) C3-C$ cycloalkyl;
(c) phenyl, which is independently substituted with 0-2 R' substituents;
(d) naphthyl, which is independently substituted with 0-2 R' substituents;
and (e) a monocyclic or fused bicyclic heterocyclic ring system having from 5 to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R' substituents;
R' is selected from:
halo, C,~alkyl, -CN, (CHZ)mNR2R3, SOzNR2R3, SOZRz, CF3, ORz, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S;
Rz and R' are independently selected from the group consisting of:
H, C,~alkyl and Co~alkylaryl, m is an integer of 0-2;
Y is a member selected from the group consisting of a direct link, -C(=O)-, -N(R4)-, -C(=O)-N(R')-, -N(R°)-C(=O)-, -SOZ-, -O-, -SOZ-N(R4)- and -N -SOZ i R4 is selected from:
H, C,_4alkyl and Co~alkylaryl;.
D is absent or is a member selected from the group consisting of (a) aryl, which is independently substituted with 0-2 R'a substituents; and (b) a monocyclic or fused bicyclic heterocyclic ring system having from S to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R'a substituents;
S R'a is selected from:
Halo, C,~alkyl, -CN, -NO2, (CHz)mNR2aR'a, SOzNR2aR38, SOzRza, CF3, ORZa, and a 5-6 membered aromatic heterocyclic ring containing from 1-4 heteroatoms selected from N, O and S;
RZa and R38 are independently selected from the group consisting of H, C,~alkyl and Co.,,alkylaryl;
E is a member selected from the group consisting of -N(R5)_C(=O)_, -C(=O)_N(Rs)_, -N(R5)_C(=O)_N(R6)_, -SOz_N(R5)_, -N(RS)-SOZ-N(R6)- and N(RS)-SOZ N(R6)-C(=O)-;
RS and R6 are independently selected from:
H, C,~alkyl, C~,alkylaryl, C°~alkylheteroaryl, C,.~alkylCOOH and C,~alkylCOOC,~alkyl;
G is selected from:
-CR'R8- and -CR'R$a-CR'~Rgb-wherein R', Rg, R'a, R88, R'~ and R$b are independently a member selected from from the group consisting of hydrogen, C,_4alkyl, Co.~alkyl-C3_gcycloalkyl, Co~alkylaryl, -OR9, -C~alkylCOOR9, -Co.~alkylC(=O)NR9R'°, -N(R9)COR'°, -N(R9)C(=O)R'°, -N(R9)SOZR'°, and common amino acid side chains;
R9 and R'° are independently selected from:
H, C,~alkyl and C°~alkylaryl;
J is a member selected from the group consisting of a direct link, -CH(R")- and -CH(R")-CHZ-;
R" is a member selected from the group consisting of:
hydrogen, C,~alkyl, Cz_6alkenyl, Cz_6alkynyl, C,_gcycloalkyl, C~alkylaryl, C~alkylheterocyclics, CHzCOOC,~alkyl, CHZCOOC,~alkylaryl;
Z is a member selected from the group consisting of (a) aryl, which is independently substituted with 0-2 R'b substituents;and S (b) a monocyclic or fused bicyclic heterocyclic ring system having from to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R'b substituents;
R'b is selected from:
halo, C,~alkyl, -CN, -NOz, NRzbR36~ SOZNRzbR3b~ SOZRzb, CF3, ORzb, O-CHz-CHz ORzb, O-CHZ COORzb, N(Rzb)-CHz-CHz-ORzb, N(-CHz-CHZ ORzb)z, N(Rzb)-C(=O)R3b, N(Rzb)-SOz-R3b, and a 5-6 membered aromatic heterocyclic ring containing from 1-4 heteroatoms selected from N, O and S;
Rzb and R3b are independently selected from the group consisting of H, C,~alkyl and Co~alkylaryl;
L is selected from:
H~ -CN~ C(-O)~12R13' (CHz)~WzR~s~ C(_~12)NR.'zRl3~ yzRi3, OR'z, -~12C(-~12)~12R13 ~d NR'zC(=NR'2)-R13;
R'z and R'3 are independently selected from:
hydrogen, -OR'°, -NR'4R's, C,~alkyl, Co~alkylaryl COOC,~alkyl, and COO-Co~alkylaryl;
R'4 and R's are independently selected from:
H and C,~alkyl; and and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
In a further preferred embodiment, the present invention provides a compound according to the formula I:
A-Y-D-E-G-J-Z-L
wherein:
A is selected from:
(a) phenyl, which is independently substituted with 0-2 R' substituents;
and (b) a monocyclic or fused bicyclic heterocyclic ring system having from S to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R' substituents;
R' is selected from:
halo, (CHZ)mNRzR', SOzNRzR3 and SOZRZ;
RZ and R3 are independently selected from the group consisting of H and C,_4alkyl;
Y is a member selected from the group consisting of a direct link, -C(=O)-, - SOz- and -O-;
D is a member selected from the group consisting of:
(a) phenyl, which is independently substituted with 0-2 R'a substituents;
and (b) a monocyclic or fused bicyclic heterocyclic ring system having from 5 to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R'a substituents;
R'a is selected from:
Halo and C,~,alkyl;
RZa and R3a are independently selected from the group consisting of H, C,~alkyl, Co~alkylaryl;
E is a member selected from the group consisting of:
-N(RS)-C(=O)- and -C(=O)-N(RS)-;
RS and R6 are independently selected from:
H, C,~alkyl, C°~alkylaryl and C°~alkylheteroaryl;
G is selected from:
-CR'Rg- arid -CR'Rga-CR'~RBb-wherein R', R8, R'a, Rga, R'~ and R$b are independently a member selected from from the group consisting of hydrogen, C,~alkyl, C~alkyl-C3_gcycloalkyl, C°~alkylaryl, -OR9, -C°~alkylCOOR9, -C°_4alkylC(=O) NR9R'°, -C°~alkylC(=O)NR9-CHz-CHz-O-R'°, -Co_aalkylC(=O)NR9(-CHz-CHz-O-R'o-)z, -N(R9)COR'°, -N(R9)C(=O)R'°, -N(R9)SOZR'°, and common amino acid side chains;
R9 and R'° are independently selected from:
H and C,~alkyl, wherein the NR9R'° group of R', Rg, R'a, RBa, R'~ and R8b is optionally cyclized to form a 5-8 membered heterocyclic group;
J is a member selected from the group consisting of a direct link, -CH(R")- and -CH(R")-CHz-;
R" is a member selected from the group consisting of:
hydrogen, C,~alkyl, Cz_6alkenyl, C°~allcylaryl and a C°~alkylheterocyclic ring;
Z is a member selected from the group consisting of (a) phenyl, which is independently substituted with 0-2 R'b substituents;
(b) an aromatic heterocyclic ring having , from 5 to 10 ring atoms, wherein 1-4 ring atoms are selected from N, O and S, and wherein the ring may be subsituted independently by from 0-2 R'b substituents;
and (c) a fused aromatic bicyclic heterocyclic ring system having from 5 to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, wherein the bicyclic ring system may be substituted with 0-2 R'b substituents;
R'b is selected from:
halo, C,~alkyl, OH, OBn, O-CHz-CHz-OH, O-CHz-CHz-OCH3, S O-CHZ-COOH, O-CHz-C(=O)-O-CH3, NHZ, NH-CHz CHZ O-CH3, NH-C(=O)-O-CH3, and NH-SOZ CH3;
L is selected from:
H~ C(-O)yzRts~ (CHz)nWzRts ~d C(=NR'z)NR'zRta;
R'z and R" are independently selected from:
hydrogen and C,~alkyl;
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
In a further preferred embodiment, the present invention provides a compound according to formula I:
A-D-E-G-J-Z-L
wherein A is a member selected from the group consisting of OZNHZ OZNHMe OzNHBu(t) OZMe HZNHZ HzNMeZ
D is a member selected from the group consisting of / \ /- / \ / \
F
F F F
/ \ / \ / \
F a F
E is a member selected from the group consisting of::
-C(=O)-NH-, -C(=O)-N(-CH3)-, C(=O)-N(-Bn)-, -NH-C(=O)-, -N(-CH3)-C(=O)- and -N(-Bn)C(=O)-;
G is selected from:
-CH-(-NHz)-CHZ-, -CH-(-NH(C(=O)-CH3))-CHZ-, -CH-(-NH(C(=O)-Ph))-CHz , -CH-(C(=O)-OR$)-, -CH(-R')-, -CHZ CH(C(=O)-OR$)-, and -CHZ-CH(C(=O)-N(-R8, -R$))-;
R' is a member selected from the group consisting of H, phenyl, Bn, -O-loweralkyl and cyclohexyl;
R8 is a member selected from the group consisting of H, C,_6alkyl, -O-loweralkyl and C3_6cycloalkyl;
J is a member selected from the group consisting of;
a direct link, -CH(R")- and -CH(R")-CHz ;
R" is a member selected from the group consisting of H, methyl, phenyl and benzyl; and Z and L taken together are a member selected from the group consisting of:
OCHzCOOH OH F OMe OCHZCHzOH OCHzCHZOMe \ \
I/ I/ I/ I/ I/ I/ I/
HzN NH H2 NH Hz NH Hz NH Hz NH Hz NH Hz NH
OCHZCOOMe NHCHzCOOH N(CI-llCHzOMe~ NH(CHZCCHzOMe) I\ I\ I\ I\ I/_ I/
/ F ~OH
/ / /
Hz NH Hz NH
Hz NH HzN NH Hz NH HzN NH
\ \ \
\ \ \ I I I I
I
/ I / \ / NH / O / S /
Nhz I ~ -N -N -N
Hz O HzN HzN HZN HzN Hz NH
OH NHz OH NHz \ \
\ \
/ I \ I / I / I / S I / NH
\ ~NH ~O
N~ I / N N ~NHz ~NH2 H2N O N~ HyN HyN
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
The following non-limiting tables illustrate representative compounds of the present invention:
Table 1 R~ Rtn, Rib H H H
Me H OH
I \ F H
-OH F
OH
Br OH
Hy-O
OCH2Ph F
CHyCH ~O~
O
~ OCH2CH20Me H
CHZCHZ"NHMe O
JI~I H H
CHZCHZ"NMe2 O
H H
CHZCH ~N
Formula II
Table 1 a 1b"
R7 Rlb H H H
Me H OH
F H
/ -OH F
Hz OH
/ Br OH
Hz Me Hz OCHZCHZOMe / OCH 2Ph F
CHz CHzCOOH
OCH2CH20Me H
Hz HN
H , H
Hz N H H
CHz Formula II
Table 2 R7 Rtb H H
MB H
\ F
-OH
OH
Bf \ -NH2 ~ ~ OCH 2Ph CHZCHZ"O' O
OCH2CH20Me CHZCH ~NHMe ~ H
CHZCHZ' _NMez H
CHZCH ~N
Formula III
Table 2a m H H
Me H
F
I\
/ -OH
CHz OH
/ Bf CHz Me CHz OCHZCHZOMe / OCH 2Ph Hz CHzCOOH
OCH2CH20Me CHz HN~N
H
BnN ~N H
Hz Formula III
Table 3 H H
Me H
I \ F
I \
-OH
/.
H
Br O
~~ OCH 2Ph CHZCHz"O' ~ OCH2CH20Me CH2CH2"NHMe O
~II H
CHZCHZ"NMe2 O
H
CHZCH ~N
Formula N
Table 3a H H
Me H
F
-OH
H
H
/ Bf Hz OMe CHz OCHzCHzOMe / OCH2Ph Hz OCHZCOOH
OCH2CH20Me CHz HN
H
Hz BnN \ H
CH~z Formula N
Table 4 H H
Me H
\ F
-OH
OH
Br HZ-\ -NH2 ~II~ OCH 2Ph CHZCH2 _O' OCH2CH20Me CHZCH ~NHMe ~ H
CH2CH2"NMez ~ H
CHZCHz' _N
Formula V
Table 4a Rat H H
Me H
F
/ -OH
CHz H
\
/ Bf OMe \
CHZ
CHZCHZOMe / OCH2Ph CHZ
CHZCOOH
OCH2CH20Me CHZ
H
H
CHz Bn~N H
Cf H/I~'z Formula V
Table 5 R R
H H
Me H
\ F
-OH
OH
Br H ~-\ -NH2 OCH2Ph CHyCH ~O~
~ OCH2CH20Me CHZCHz _NHMe O
~II H
CH2CH2"NMez ~ H
CHZCHZ' -N
Formula VI
Table Sa R Rib H H
Me H
F
/ -O H
CHz H
/ Br CHZ
Me CHZ
CHZCH20Me / OCH2Ph CHZ
CHzCOOH
OCH2CH20Me CHz H
CHZ
Bn~N H
ICH/I~z Formula VI
Table 6 R7 i H H
Me H
I \ F
I \
-OH
OH
Br Hz-I \ -NH2 O
~II~ OCH2Ph CH2CHZ _0-~II OCH2CH20Me CHZCHZ _NHMe ~ H
CHZCHZ"NMez ~ H
CHZCH2"N
Formula VII
Table 6a OZNHz Rtb /
R~
N
Formula VII
R7 Rib H H
Me H
F
/ -OH
OH
/ Br CHZ
Me CHI
CHZCHZOMe / OCH 2Ph CHZ
OCH2CH20Me CHZ
HN
H
CHZ
Bn~N H
C[H/I~z Table 7 Formula VIII
A D A D
OZNHz HzNMez F
/ \ / \ / \ / \
CI
OzNHMe / \ / ~ / \ / \
F
OzNHBu(t) / \ / ~ / \ / \
CI
OZMe F
/ \ / \ / \ /-\
F
HzNH F
/ \ / \ Hz / \
F
H2NHMe H
z / \ / ~ / \
F
Table 8 A D A D
OZNHz HZNMeZ F
/ \ / \ / \
CI
OzNHMe / \ / ~ / \ / \
F
OZNHl3u(t) / \ / ~ / \ / \
CI
OZMe F
/ \ / \ / \ / \
F
HZNH F
/ \ / \ HZ % \ /-\
F
HZNHMe Hs / \ ~ ~ / \
F
wherein R3 is a member selected from the group consisting of H, F, -OH, Formula IX
Br, Cl, -NHz, -O-CHz-O-Ph and -O-CHZ-CHz-O-CH3, Table 9 Formula X
A D A D
OZNHz HzNMez F
/ \ / \ / \ / \
CI
OzNHMe / \ / ~ / \ / \
F
OpNHBu(t) / \ / ~ / \ / \
CI
O2Me F
/ \ / \ / \ / \
F
/ \ / \ HZ % \ /-\
F
H NHMe / \ 2 / \ H / \
F
Table 10 Formula XI
A D A D
OZNHx HzNMex F
CI
OzNHMe /
F
OzNHBu(t) /
CI
02Me F
/ ~ / \
F
HxNHx F
Hx /
F
HZNHMe Hx / ~ / \ /
F
Table 11 Formula XII
A D A D
OZNHZ HZNMe2 F
/ \ / \ / \ / \
CI
OZNHMe / \ / \ / \ / \
F
OZNHBu(t) / \ / \ / \ / \
CI
OzMe F
/ \ / \ / \ / \
F
HZNHp F
/ \ / \ HZ % \ /-\
F
HyNHMe Hx / \ / ~ / \
F
Table 12 Formula XIII
A D A D
OZNHZ HZNMez F
CI
OZNHMe /
F
OZNHBu(t) /
CI
02Me F
% ~ / \
F
HZNH F
HZ / ~ /-\
F
HzNHMe Hs / ~ / ~ /
F
Table 13 Formula XIV
A D A D
OpN Hz HzN Mez F
/ \ / \ / \ / \
C
OzNHMe / \ / \ / \ / \
F
OZNHBu(t) / \ / \ / \
/ \
ci OZMe F
/ \ / \ / \ /-\
F
HzNHz F
/ \ / \ Nhz / \
F
HZN H Me Hz / \ / ~ / \
F
Table 14 Formula XV
A D A D
OzNHz H2NMez F
/ ~ /
CI
OzN H Me / ~ /
F
OZNHBu(t) / ~ /
CI
OZMe F
/ ~ / ~ / ~ / \
F
HzNHz F
/ ~ / \ Nhz /
F
HzNHMe Hz / ~ /
N
F
Table 15 Formula XVI
A D A D
OZNHz HZNMez F
C
OZNHMe F
OzNHl3u(t) CI
OZMe F
F
HyNHp F
~ ~ ~ Nnz / ~ / \
F
HZN H Me HZ
F
Table 16 Formula XVII
A D A D
OzNHp HZNMez F
C
OpNHMe F
OZNHBu(t) CI
O2Me F
F
HzNHy F
NhZ
F
HZNH Me HZ
F
Table 17 02NH2 R1b' R1b"
\ ~ NH2 H ~
Formula XVIB
R7 ~ R11 ~ R1b' R1b"
H H H H
Me H H OH
\ \
F H
/ -OH F
C Hz OH
OH
\
/ OH OH
CHZ
H OMe I \ / -NH2 H
Table 18 OpNHz O / I \
\ /N
H
R~ R~~ NH2 Formula XX
R~ R~~ R~ R~~
H \
I I/
OH
H
Me H I /
CHz HZ_ OMe \ I/ I\ /
/ /
CHZ
Table 19 02NH2 _ / I \
FNi \ / N
R~ R~~ NH2 Formula XX
R~ R~~ R7 R11 H H I I /
/ CHx OH
H
Me H I /
CHZ
HZ_ Me I\ I/ I\ I/
/ /
CHZ
Table 20 OZNHZ / N~
\
NHz Formula XXII
R7_R~~ R~ R~~
\
H H I / I /
CHz OH
H
Me H I /
CHz Hz_ OMe I\ I/ I\ I/
/ /
CHz Table 21 OpNH2 / N~
/N
H R7 Rat NH2 Formula XXII
R~ R~~ R~ R~~
\
H H I
I/
/ CHz OH
H
Me H I /
CHz Hz_ OMe I\ I~ I\ /
/ ~
CHz Table 22 OzNH2 /
N
R~ R"
Formula XXIV
R~ R~ ~ R~ R~ ~
\ \
H H I / I /
CHz OH
H
Me H I /
CHz Hz. OMe \ / \ /
/ /
CHz Table 23 OZNHZ / N~
U N
R~ R~~
Formula XXIV
R~ R~~ R~ R~~
\
H H I / I /
CHz OH
H
Me H I /
CHz Hz_ OMe I\
I ~ I / I j /
Hz Table 24 02NH2 / ~ N
N
H R~ R»
Formula XXV
\ \
H H I / I /
CHz OH
H
Me CHz Hz_ OMe \ / \ /
/ /
~z Table 25 Rib, Rib..
02NH2 R~~ /
H
N \ NH2 R~ NI H
Formula XXVI
R7 ~ R11 ~ R1b' ~ R1b"
H H H H
Me H H OH
\ F H
/ ~/
/ -OH F
C HZ
OH
OH
\
/ OH OH
CHZ
H _ OMe 2 \
\ ~ / -NH2 H
/ CHz Table 26 OZNHZ Rib /
\ ~ NH2 H
Rya NH
Formula XXVII
Rya R7b Rya R7b \ \
H H I / I /
CHx OH
H
Me H I /
CHx Hx_ \ OMe I\ I/ I\ I/
/ / cHz Table 27 02NH2 Rib / ( \
\ /N
R7a NH2 Formula XXVIII
R7a R7b R7a R7b \
.H H I / I /
CHx OH
H
Me H I /
CHx Hx_ OMe \ / I\ I/
/ / CHx Table 28 02NH2 Rib /
H R7a NH2 Formula XXX
R7a R7b R7a R7b \ \
H H I / I /
CHx OH
H
Me H I /
CHx Hx. OMe I\ I/ I\ I/
/ /
CHx Table 29 02NH2 Rib /
H R7a NHp Formula XXX
R7a R7b R7a R7b H H I I /
/ CHx OH
H
Me H I /
CHx Hx_ Me I\ / I\ I/
/ /
CHx Table 30 OZNH2 O Rib /
R' 7a NH2 Formula XXXI
R7a R7b R7a R7b H H I / I /
CHz OH
H
Me H I /
CHz Hz_ \ OMe I\ I/ I\ I/
/ /
cHz Table 31 H
OZNHZ Rib / ~ N\
R7a Formula XXXII
R7a R7b R7a - R7b H I I/
/ CHz OH
H
Me H I /
CHz Hz_ \ OMe I\ I/ I\ /
/ /
CHz Table 32 H
02NH2 Rib / N
H ~ N
R7a Formula XXXIII
R7a R7b R7a R7b \
H
I~
CHy OH
H
Me H I /
CHz HZ. OMe I\ I~ ~\ I/
/
~z I~
Table 33 Rib, Rib.
R7b H \ NHZ
Rya HsC NH
Formula XXXIV
Rya ~ Rib ~ Rib' ~ R1b"
H H H H
Me H H OH
\ \
F H
/ ~ /
-OH F
CHZ
OH
H
/ OH OH
CHZ
H _ Me 2 \
\ I / -NH2 H
/ CHZ
-NH 2 Me H F
-NH Ac Me H H
NHS02Me Me H H
Table 34 02NHz Rib /
\ ~ NHZ
H I, K' a H3~
Formula XXXV
R7a ~ R7b H H
Me H
/ ~ /
CHz OH
H
CHz H - Me \ /
/ CHZ
-NH 2 Me -NH Ac Me NHS02Me Me Table 35 02NH2 Rib / ~ \
\ /N
Rya H3~ NH2 Formula XXXVI
Rya ~ R7b H H
Me H
\ \
/
/
/
cHz OH
H
CHz Me z_ \
/ CHz -NH 2 Me -NH Ac Me NHS02Me Me Table 36 02NHz Rib / N\
Rra Formula XXXVII
Rya H H
Me H
\ \
/ ~ /
\ ~ /
CHz OH
H
CHz _ Me z \
\ /
/ CHz -NH 2 Me -NH Ac Me NHS02Me Me Table 37 OZNH2 Rib ~ ~ S~
R'a H3C NH2 Formula XXXVIII
7b H H
Me H
\ \
/ ~ /
CHz OH
OH
CHz H _ Me \ /
/ CHz -NH 2 Me -NH Ac Me NHS02Me Me Table 38 02NHz Rib /
~a H3~ v NHp Formula XXIX
R7a ~ R7b H H
Me H
\ \
/ ~ /
/
CHZ
OH
H
CHz H - Me \
\ /
/ CHz -NH 2 Me -NH Ac Me NHS02Me Me Table 39 OzNH2 Rib / N\
N N
K' a Hg~
Formula XXXX
R7a ~ R7b H H
Me H
\ \
/ ~ /
CHi OH
OH
CHz H _ Me \ /
/ CHZ
-NH 2 Me -NH Ac Me NHS02Me Me Table 40 OZNH2 Rib / N
N
H
Rya H3C
Formula XXXXI
R7a ~ R7b H H
Me H
\ \
/ ~ /
/
/
CHZ
OH
H
CHy H - Me \ /
/ C
-NH 2 Me -NH Ac Me NHS02Me Me Table 41 H
Rib. Rib.
02NH2 Rib /
NHZ
v v Formula XXXXII
Rib ~ R» ~ Rib' ~ R1b"
H H H H
-C(= O)NCH 2CH 20C H3 H H OH
\ \
F H
-O H F
CHy OH
H
/ OH OH
CHZ
H2- Me \ / -NH 2 H
CHZ
-COOH Me H F
-COOC H3 ~ Me H H
-C(=O)N(CH3)2 ~ Me H H
Table 42 Formula Rib ~ R»
H H
-C(=O)NCH 2CH 20C H3 H
\ \
/ ~ /
CHZ
OH
H
CHz H - Me z \
\ /
/ CHZ
-COOH Me -COOC H3 Me -C(=O)N(CH3)2 Me Table 43 H
02NH2 Rib / ~ \
\ /N
R~~ NHz Formula XXXXIV
Rib ~ R~~
H H
-C(= O~1CH 2CH 20C H3 H
\ \
CHZ
OH
OH
CHi H - Me \ /
/ CHz -COOH Me -COOC H3 Me -C(=O)N(CH3)2 Me Table 44 H
02N H2 Rib HO / ~ N\
H Rig NHz Formula XXXXV
H H
-C(=O)NCH 2CH20CH3 H
\ \
/ ~ /
CHZ
OH
H
CHZ
H _ Me \ /
/ CHz -COOH Me -COOC H3 Me -C(=O)N(CH3)2 Me Table 45 02NH2 R~bHO / S
~H2 Formula XXXXVI
Rig H H
-C(= O)NCH 2CH 20C H3 H
\ \
\
~z OH
H
CHz _ Me \
\ /
/ CHz -COOH Me ~OOC H3 Me -C(=O)N(CH3)2 Me Table 46 02NHz O Rrd-10 / O\
N w ~ /
H v t~ ~H2 Formula XXXXVII
Rib ~ Rt ~
H H
-C(= O~1CH 2CH 20C H3 H
\ \
/ ~ /
CHz OH
H
CHz H - Me \ /
/ ~z POOH Me -COOC H3 Me -C(=O)N(CH3)2 Me Table 47 O pN H2 R~bHO /
N N
\/ \/ H " ~,"
Formula XXXXVIII
Rm H H
-C(=O)NCH 2CH20CH3 H
\ \
/ ~ /
CHZ
OH
OH
CHz H - 1 Me \ /
/ CHZ
-COOH Me -COOC H3 Me -C(=O)N(CH3)2 Me Table 48 OZNH2 R~bHO / H
N
N
Rtt Formula XXXXIX
Rte H H
-C(= O)NCH 2CH 20C H3 H
\ \
/ ~ /
\
CHi OH
H
CHy H _ Me / CHZ
-COOH Me -COOC H3 Me -C(=O)N(CH3)2 Me Table 49 Rib 02NH2 Rs Rib /
N \ ~ NH2 O Rya ~H
Formula L
R5 Rya ~ Rib ~ Rib H H H H
Me Me H
H
\ I Me /
HzC ~ ~ ~ / Bn OH
CHz H
\ _ / HyC ~ /N OMe CHz H - Me z \ _ \ / HZC
Ogn / CHz H , -CH 200H HzC ~ / OH OCH 2C0 OH
Me -CH 2CH 2COOM a HzC ~ ~ NHz OCH 2CH 20M a gn -CH2CH2CONMe2 HzC ~ ~ OH
Table SO
02NH2 Rs Rib /
N \ ~ NHZ
- _ O Rya ~H
Formula LI
Rs ~ R7a R7b H H H
Me Me H
\ \
Me / ~ /
Hzc ~ ~ ( / Bn CHz OH
\ _ / HZ°
CHz H _ Me z \ _ \ / Hz0 ~ N
/ CHz H -CH 200H Hz0 ~ / OH
Me -CH 2CH 2COOM a Hzc ~ ~ NHz gn -CH2CH2CONMe2 H2c Table 51 02NH2 Rs Rib / \
N \ ~ /N
R7a Formula LII
R5 ~ R7a ~ R7b H H H
Me Me H
\ I \ Me /
HZc ~ ~ ~ / en CHz OH
\ _ HZC ~ / N
CHz Me H i- \ _ \ / HZC ~ N
/ CHz H -CH 200H HaC \ / OH
Me -CH 2CH 2COOM a gn -CH2CH2CONMe2 H=c Table 52 H
02NHz Rs Rib / N\
_ w_ O Rya NH2 Formula LIII
Rs ~ R7a H H H
Me Me H
\ \
Me I/ I/
HzC ~ \ I / Bn CHz OH
\ _ CHz H _ Me \ / HzC ~ N
/ CHz H -CH 200H HaC ~ / OH
M HzC ~ ~ NHz -CH 2CH 2COOM a -CH2CH2CONMe2 Hzc Table 53 OZNH2 Rs Rib / S
~1~
O Rya NHZ
Formula LN
Rs ~ R7a H H H
Me Me H
\ I \ Me I/
Hzc ~ \ I / Bn CHz H
\ _ HZC
CHy H _ Me \ / HzC
N
CHz H -CH 200H HzC ~ / OH
M HOC ~ ~ NHZ
-CH 2CH 2COOM a gn -CH2CH2CONMe2 HZ°
Table 54 02NH2 Rs Rib / O
~N
O Rya NHZ
Formula LV
Rs ~ R7a R7b H H H
Me Me H
\ I Me I/
Hzc ~ ~ I / Bn CHZ
OH
\ _ I / H'° \ /
CHz H - Me 2 \ _ \ / HZC
N
/ CHZ
H -CH 200H HxC \ / OH
Me -CH 2CH 2COOM a gn -CH2CH2CONMe2 HzC ~ ~
_77_ Table 55 H
02NH2 Rs Rib / N\
R7a _ Formula LVI
Rs ~ R7a ~ R7b H H H
Me Me H
\ I Me /
H20 ~ ~ ~ / Bn CHz OH
\ _ HZC
CHz Me H z- \
\ / HZC
CHz H -CH 200H Hx0 ~ / OH
Me 2 ~ I 2 -CH 2CH 2COOM a gn -CH2CH2CONMe2 H2C
_78_ Table 56 02NH2 R5 Rib / H
N
N ~ N
R7a Formula LVII
R7a H H H
Me Me H
Me H2c ~ ~ I / Bn CHz H
\ _ HyC
CHz " _ Me z \ _ ~ / "Z~ \ /
/ N
CHz H -CH 200H "zc \ / OH
M "2C \ ~ N"z -CH 2CH 2COOM a ga -CH2CH2CONMe2 HZc \
Table 57 Rib 02NH2 I5 Rib /
N \ ~ NH2 O Rya ~H3 ~H
Formula LVIII
R5 ~ Rya ~ Rib R
H H H H
Me Me H
H
\ I \ Me F
I /
HZ~ ~ ~ I / Bn OH
~2 OH
\ _ / HZC ~ ~N OMe CHz H - Me \ / HzC
/ CHz N OBn H -CH 200H HzC ~ ~ OH OCH 2C0 OH
HzC Hz Me -CH 2CH 2COOM a ~ ~ OCH 2CH 20M a gn -CH2CH2CONMe2 Hzc ~ / OH
Table 58 OZNHZ R5 Rib /
N \ ~ NHz O Rya ~Hg ~H
Formula LIX
Rs ~ Rya Rib H H H
Me Me H
Me /
HZC ~ \ ~ / Bn CHZ
OH
\ _ HzC
CHz Me H y- ~ _ \ / HZC ~ N
/ CHz H -CH 200H HxC ~ / OH
Me -CH 2CH 2COOM a HzC \ / NHZ
gn -CH2CH2CONMe2 Hzc Table 59 02NH2 I5 Rib / \
N \ ~ /N
7a H3~ ~H2 Formula LX
R7a ~ R7b H H H
Me Me H
\ \
I / I / Me HZc ~ ~ I / Bn CHZ
H
\ _ / HzC
CHZ
MB
H 2- \
\ / HzC
N
/ CH=
H -CH200H HZc ~ ~ ~H
Me ~ HzC ~ ~ NHZ
-CH 2CH 2COOM a gn -CH2CH2CONMe2 H=c Table 60 H
OZNH2 R5 Rib / N\
w_ Formula LXI
R5 ~ R7a H H H
Me Me H
\ I Me I/
Hz0 ~ \ I / Bn CHz OH
\ _ HZC
CHz H - Me \ / HzC ~ N
/ CHz H -CH 200H HzC ~ / OH
Me -CH 2CH 2COOM a Hz0 \ / NHz Bn -CH2CH2CONMe2 HZ°
Table 61 OzNH2 R5 Rib /
N I /N
O Rya H3C NH2 Formula LXII
R7a R7b H H H
Me Me H
\ \
Me I/ I/
HZC ~ ~ I / Bn CHZ
OH
\ _ HzC
CHI
H - Me \
\ / HZC
N
/ CHI
H -CH 200H HaC \ / OH
Me -CH 2CH 2COOM a HzC \ / NHZ
gn -CH2CH2CONMe2 HZ~
Table 62 OZNH2 RS Rib /
~\N
O Rya H3C NHp Formula LXIII
R7a ( R7b H H H
Me Me H
\ \
Me HZc ~ ~ ~ / Bn CHZ
OH
\ _ HZC
CHp H - Me \ / HZC
N
/ CHy HZC ~ ~ OH
M H2C ~ ~ NHz -CH 2CH 2COOM a gn -CH2CH2CONMe2 H,c Table 63 H
OZNH2 R5 Rib / N\
U ~N
O
Formula LXIV
R7a ~ R7b H H H
Me Me H
\ \
/ / Me HOC ~ ~ I / Bn CHZ
OH
\ _ / HyC
H _ Me \ / HzC
N
H -CH 200H HzC ~ / OH
Me -CH 2CH 2COOM a HzC ~ ~ NHz gn -CH2CH2CONMe2 HZC
Table 64 H
02NH2 Rs Rib / N' ~NH2 N
O Rya H3C
Formula LXV
Rs ~ R7a R7b H H H
Me Me H
\ I Me I/
H2~ ~ ~ I / Bn CHZ
OH
\ _ / HzC
CHz Me H 2_ \
\ / HpC
N
/ CHZ
H -CH200H H2C ~ / OH
M HZC ~ ~ NHS
-CH 2CH 2COOM a gn -CH2CH2CONMe2 HZO
_87_ Table 65 Rib H
02NH2 I5 Rib /
N \ ~ NH2 O R~~
Formula LXVI
R5 R7b R~~ ~ 1b R
H H H H
Me Me H
H
\ I Me F
/
Hz~ ~ ~ ~ / Bn OH
~z OH
\ _ / HZC ~ /N OMe CHZ
H - Me \ / HZ° ~ I
/ CHZ N OBf1 H -CH 200H HsC \ / OH OCH 2C0 OH
HxC NHz Me -CH 2CH 2COOM a ~ ~ OCH 2CH 20M a -CH2CH2CONMe2 Hz~ ~ ~ OH
_g8_ Table 66 N
O
Formula LXVII HN~ 'NH2 R7b ~ R1~
H H H
Me Me H
\ \
Me / ~ /
Hzc ~ ~ I / gn CHz OH
\ _ / HzC
CHy H z- Me \ / H2C ~ N
/ CHz H -CH 200H HxC \ ~ OH
Me -CH 2CH 2COOM a HzC \ / NHz -CH2CH2CONMe2 H=c Table 67 OZNH2 5 ~bHO / \
N R \ ~ /~
Formula LXVIII
Rs ~ Rib ~ R~~
H H H
Me Me H
\ \
I I / Me HZc ~ ~ I / Bn CHz OH
\ _ / HzC
CHz H _ Me z \
\ I / HzC ~ N
/ CHz H -CH 200H HzC ~ / OH
Me 2 ~ I
-CH 2CH 2COOM a gn -CH2CH2CONMe2 HZc Table 68 OZNHz Rs R~t~NO / N\
w ~ /
O R» v NHZ
Formula LXVIX
Rs H H H
Me Me H
\ \
Me I/ I/
HzC ~ \ / Bn CHz OH
\ _ / HzC
CHI
H - Me \
\ / HzC
N
/ CHz H -CH 200H HzC \ / OH
Me HzC ~ ~ NHz -CH 2CH 2COOM a -CH2CH2CONMe2 H,c Table 69 OzNHz Rs R~bHO
w O » v NH2 Formula LXX
Rs ~ Rib ~ Rtt H H H
Me Me H
\ I Me /
H~~ ~ ~ ~ / Bn CHz H
\ _ HzC
CHZ
H - Me \ / HzC ~ N
/ CHZ
H -CH 200H HxC \ / OH
Me -CH 2CH 2COOM a HzC ~ ~ NHZ
gn -CH2CH2CONMe2 HZ~
Table 70 w_ ~ /
O R» NHz Formula LXXI
H H H
Me Me H
\ I Me /
HZC ~ \ ~ / Bn CHz H
\ _ CHZ
Me H Z- \
\ / HzC
N
/ CHz H -CH 200H HaC \ / OH
Me -CH 2CH 2COOM a HzC \ / NHz -CH2CH2CONMe2 H2C
Table 71 02NH2 Rs R~t~O / N\
N
O
Formula LXXII
H H H
Me Me H
\ \
I / I / Me Hzc ~ ~ I / Bn CHz OH
\ _ HZC
CHz H - Me \ / H2C
N
/ CHz H -CH 200H HzC ~ / off Me -CH 2CH 2COOM a -CH2CH2CONMe2 H2c Table 72 02NHZ RS R~bHO
~NH2 N
O R~~
Formula LXXIII
R5 ~ Rib ~ R~~
H H H
Me Me H
\ \
I I / Me I\
H2c ~ \ / Bn CHz OH
\ _ / HzC
CHz H _ Me z \ _ \ / Hzc N
/ CHz H -CH 200H HzC ~ / OH
M HzC ~ ~ NHz -CH 2CH 2COOM a gn -CH2CH2CONMe2 Hzc Table 73 / SOxNHz SOZNHx /
\ \ / \ I \ Me /
I / N \ I NHz / \ I NHx / SOZNHx /
I \ I / SOxNHx O
\ \ / \I II
\ home /
~N \ I NH Iz I / N \ I NHz O NH
O NH
/ SOZNHx /
\ I \ N / SOZNHx i \ / I
I / N \ I NHz \ \ /
O NH / N \ I NHx O NH
Table 74 / SOzNHZ / SOpNHz \ \ H H \ \ H Bn / N \ / N \
o I / o ~
HN' ~NHp HN ~ ~NH, / SOzNHz Me0~0 SO NH HO O
/ ~ z z \ \ \
'\~H
/ N \
o ~ / o HN' ~NHz HN NHz / SOzNHz \
/ N ~ / SOsNHz O ~ ~ ~ \ \
H
N / N
O
HzN ~N
Other preferred compounds of formula I, having the sub-formula Ia, are set forth in Table 75, below.
Table 75 Formula Ia R~
o-z- z x - Phenyl- m_C~_ z o-x- x z -P m- z - _ enY
o-z- z -p enYl o-z- z z ~- P~ m-Ct=~ z o_z- z 3_ _phenyl W -C(=NH)NHZ
o-z- z z n_ eny m~(= z _p o x- z x p m-C(=O)NHx = eny o-r x z -p m_ eny o-z- x x -p m~~-0)~Z
eny o-x- z z 3_ p m_ eny o-z- z z j- -p eny m- x o-x- z x n_ eny m- z _p -o-x- z z a p- -~~z o-z- x x me P' z o-z- x z -am p- x me o-z- z x 3-am p-C
me o-z- x x a- P- z a o-z- z z n_ p_ x _~
me o-z- x z me p- x o-x- z x -am p-~,(=V)Nttx me o-z- x z -am p- x me o-z- z z 3-am p_ x me o-x- z x 3- p- x -am me o-z- x z n_ p- z _~
a o-r z x eny m- IVH)NHZ
-ammo-car oxy is acid o-SUz-Nriz H LHx m-rnenyt-ammo m- z carboxylic acid o-SUx-NHz H ~:Hx r-pnenyt-ammo m- z carboxylic acid o-SUx-NHx H c:Hz Ltt3-pnenyt-ammo m-~(=riri)r~riz carboxylic acid o-5Ux-NHx H c:Hx LH3-U-phenyl m-V(=rrri)r~rix ammo carboxylic acid o-SUz-NHz H c:Hz tsn-u-pnenyi m-~(=r~ri)wriz ammo carboxylic acid o-5Ux-NHx H c:Hz rnenyt-ammo m-~(=u)r~rix cardoxyttc acid o-SUz-NHz H c:Hx L1-pnen yt-ammo m-~(=v)Nriz carboxy lic acid o-SUz-NHx H c:Hz r-pnenyt-ammo m- z carboxylic acid o-SUx-NHx H ~ c:Hz c:H3-phenyl-ammo m- x carboxylic acid x c m (~)~x uo carboxylic a d o-5Ux-NHz H (:Hz tin-u-pnenyi-ammo m-~;(=u)Nrix carboxylic acid o-z- x z a m- =NH N
y z p enoxy-acetic aci ester o- z- 2- H CHz Mettryl m-C(=NH)NHz - Cl-phenoxyacehc acid ester o- z z H CHz Methyl m- z F-phenoxy-acetic acid ester o-5Uz-Nriz H LHz Metnyi m- z ~ri3-pnenoxy-acetic acid ester o-5Uz-NHz H LHz Metnym:rij-u-pnenoxy- m- z acetic acid ester o-SUz-NHz H c:Hz Memyi m- z tsn-u-pnenoxy acetic acid ester o- r z CHz Methyl m- z Yhenoxyacehc acid ester o- z- z CHz Methyl m-C(=V)NHz C1-phenoxyacehc acid ester o- z- z z a m- z y -p enoxyacehc acid ester o-5Uz-NHz H c:Hz Memyi m- z t.H3-pnenoxy-acetic acid ester o-SUz-NHz H (:Hz a m- z y -p epoxy acetic acid ester o-SUz-NHz H (:Hz a m- z y n--p epoxy acetic acid ester o- z- z z enoxyacetic m- z aci o- z z z -p m-(:(=NH)NHz epoxy-acetic aci o- z- z z -p m- z epoxy-aceric aci o- z- z z 3-p m- NHz epoxy-acetic aci o- r z z 3- m-C(=NH)NHz -p epoxy-acetic acid o- z- z z n- m- z -p epoxy acetic aci o- z- z z enoxyacehc m- z aci o- z- z z -p m-(:(=U)NHz enoxyacehc aci o- r z z -p m- z enoxyacehc -aci o- z- z z 3- p m- z epoxy-aceric aci o- r z z 3 m- z -p epoxy acetic acid o- z- z z n- m- z -p epoxy acetic aci o- z z z enoxye m-~;~=mryvriz ano o- z- z z -p m- z epoxy-a ano o- z- z z -p m-C~~H)NHz epoxy-a ano o- r z z j-p m- z epoxy-a ano o- z- z z 3- p epoxy-a m-- ano o- z- z z n- epoxy a m- z -p ano o- z- z z enoxye m- z ano o- z- z z -p m- (=O)NHz enoxye ano o- r z z -p m- z epoxy-a ano o- z- z z j-p m-~:~=u)ivriz epoxy-a ano o- z- z z s- P epoxy- m- z - a ano o- z- z z n_ epoxy- a m-~:~=u~ivriz _p ano o- r z z a m- z y p epoxy-a y ether o-SUz-NHz H c:Hz Metnyi m- z Li-pnenoxyetnyi ether o-SUz-NHz H Lriz Metnyi m- z r-pnenoxy-emyi ether o-~Uz-NHz H c:Hz Memym;ti3-pnenoxy- m-~~=mryvriz ethyl ether o-5Uz NHz H c:Hz nnetnyi m- z ~ri3-u-pnenoxy-ethyl ether o-SU2 NHz H LHz 1\necnyi m- z tin-u-pnenoxy ethyl ether o-z- z z a m-~~=u)wriz y ienoxye y ether o-5U2-NH2 H l;Hz Metnyll:l-pneriOXyeLtlyl m-l:(=u)1Vt12 ether O-5UZ-NHZ H ~riz Memyi m-~~=u)Nriz r-pnenoxyeuiyi ether O-5Uz-NHZ H laiz Mettlyl m-~;ti3-phenoxyethylether o-5V2 Hz H LHz lmemym:ri3-u- m-~~=v)wriz N
phenoxyethyl ether o-5Uz-Nriz H calz lvlemyl m- z tsn-u-phenoxyethyl ether o-i z z- z P m- z enY
o-z- z z- z -P m- z enY
o-z- z r z -P m-C(=1QH)NHz enY
o-z- z H z- z 3 P m- z enY
o-i z z z 3- - p eny m- _ o-z- z z- z n_ eny m- z _p o-z- z z- z P z enY
o-z- z r z -P m-~l=~)~nz enY
o-z- z z- z -P m- z enY
o-r z r z a-P m- z enY
o-i z z- z 3- p eny m- =O
-o-r z z- z n_ eny m-~~=~)r~riz _p o-z- z z z me P- z o-z- z z- z -am P-CC ~~z me o-i z i z -am p- z me o-z- z r z 3-am p-C(=NH)NHz me o-z- z z- z 3 p- z -am me o-z z z z n- p-C(_~)~z -am me o-z- z z- z m p-C(=O
me o-z- z z- z -am p- z me o-z- z z- z me p-t~(=u)ivtiz o-z z i z 3-am p-~.~=u)mriz me o-z- z z- z 3- p- z -am me o-z- z z- z n_ p- z _~
me o-z- z z- z eny m-C~ NH)NHz -ammo-car oxy is acid o-5Vz-NHz H (:Hz-~:Hz eny m- z -ammo carboxylic acid o-SUz Hz H C:Hz-C:Hz r-phenyl-ammo m-~~=~ri)~ry N
carboxylic acid o-5Uz-NHz H c:Hz-ca1 y ; m- z 3-pnenyi-ammo carboxylic acid o-SUZ-NHZ H l:Hz-I:HZ 1x13-u-pnenyi m-~.~=mri)mriz ammo carboxylic acid o-5Uz-NHz H C;Hz-c:Hz rip-u-pnenyi m-~~=~ri)~riz ammo carboxylic acid o-SUz-NHz H C:Hz-LHz rneny-ammo m- z carnoxync acid o-5Uz-NHz H C:Hz-LHz Li-pnenyi-ammo m- z carboxylic acid o-5Uz HZ H C;HZ-l:Hz r-pnenyi-ammo m-~~=v)wriz N
carboxylic acid o-SUz-NHz H LHz-LHz LH3 m-~~=u)Nriz pnenyi-ammo carboxylic acid o-SUz-NHz H c:Hz-Ltiz LH3 m-~~=u)r~riz u-pnenyi-ammo carboxylic acid o-SVZ HZ H l:Hz Hz nn-u-pnenyi-ammo m-~~=u)Nriz N l;
carboxylic acid o-z- z r z a m- z y p epoxy-acetic aci ester o- z- z z z et m-C(=NH)NHz y -p enoxyacehc acid ester o-SOz-NHz H CHz CHz Methyl m- z r'-phenoxy-acetic acid ester o-JUz-Nriz r1 LHz-MHz lvletnyl m- z LH3-pnenoxy-acetic acid ester o-~uz-NHz H t,tiz-l:rizMemyi m- z cai;
u-pnenoxy-acetic acid ester o-JUz-Nriz ti t;Hz-~Hz Memyi m-~~=r~ri)wriz tsn-u-pnenoxy acetic acid ester o- z- z H CHZ CHz Methyl m-(:(=U)NHz Yhenoxyacehc acid ester o-SOz-NHz H CHz-CHz Methyl m-C(=U)NHz C1-phenoxyacehc acid ester o- z- z H CHz-CHz Methyl m- z F-phenoxyacehc acid ester o-JVZ NHz H lalz-lalz lVlelllyl m- z l;tij pneriOXy-acetic acid ester o-SUz-NHz H Lrlz-LHz a m- z y -p enoxy acetic acid ester o-5Uz-NHz H LHz-t:Hz a m- z y n--p enoxy acetic acid ester o- z z H - z- z enoxyacehc m- z - aci o- z- z z- z -p m- ~ NH)NFIz enoxy-acetic aci o- z- z z- z -p m- z enoxy-acetic aci o- z- z r z 3- p m- )NHz enoxy-acetic aci o- z- z r z 3- m-C(=NH)NHz -p enoxy-acetic acid z- z z- z n- m- z -p enoxy acetic aci o- z- z z- z enoxyacehc m-C(=O)NHi aci o- z- z z- z -p m- z enoxyacehc aci o- z- z z- z -p m-C(=O)NHz enoxyacehc aci o- r z z- z 3-p m- z enoxy-acetic aci o- z- 2 2 2 3- m- =O)NHZ
-p enoxy acetic acid o- z- z z- z n- m- z -p enoxy acetic aci z- z z- z enoxye m-ano o- z- z z- z -p m- =NF~NHz enoxy-a ano o- z- z z- z -p m- z enoxy-a ano o- z- z z- z 3 p m- =NH)NHz enoxy-a ano o- r z z- z s- - p enoxy-a m- z ano o- z- z z z n- enoxy a m--p ano o- z- z z- z enoxye m-C(=O)NHz ano o- z- z z- z -p m- z enoxye ano o- z- z z- z -p m- =O~I2 enoxy-a ano o- z- z z- z 3- p m- z enoxy-a ano o- z- z z- z 3- - p enoxy- m-~a=ul~riz a ano o- z- z z- z n- enoxy- a m- z -p ano o- z- z z z a m-C(=NH)NHz Y
p enoxy-a y ether o-5Uz-NHz H ~;Hz-~;ttz lviemyl m- z t,i-pnenoxyemyi ether o-5Uz-Nriz H c:Hz-t;Hz Memyi m- z r-pnenoxy-etnyi ether o-SUz-NHz H (aiz-c:Hz a m- z y 3-p enoxy-ethyl ether o-~Uz-Nriz H l;Hz-C.;HZ lVleTtlyllalg-u-prieriOXy- m-l:(=1Vri)iVriz ethyl ether o-5Uz-NHz H LHZ-~:HZ nnemyi m- z tsn-u-pnenoxy ethyl ether o-z- z z- z et m-y enoxye y ether O-JVZ-Nrlz t~ Lty-~tiz Metnym;i-pnenoxyemyi m-~;(=U)Ntiz ether o-i z i z a m- z y -p enoxye y ether o-JVZ-Nrlz z- z a m- z Y
phenoxyethyl ether o-JUZ-Ntly t1 1a12-lalz MeLtlyll:rl3-U- m-l;(=U)NriZ
phenoxyethyl ether o-~uz-Nriz t m :riz-~riz nnemyi m-~:(=U)ririz nn-U-phenoxyethyl ether o-z- z z- i z P m- z enY
-o-z- z z- z-z -phenyl m_C~_~)~z o-z- z z- z-z ~en~ iri_C(=NH)NFIz - -z- z z- z-2 3_ p m_~( eny -~z o-z- z z- z-z 3- - p eny m- z o-z- z z- z-z n_ eny m_C(=~z _p o-z- z i i z p m- z eny o-z- z z- z-z -P m-C(=
enY
o-i z r r z -P m- z enY
o-i z z- z-z s- P m- z enY
z- z r i z 3- - P eny m--. -o_z_ z z_ z_z n_ eny~ m-C(=O)~2 _p o-z- z z- z-z m p_ z me - i z i i z -and p-C(=NH)NH2 me -_ o-z- z z- z-z -am p-C(=~)~z a o-z- z z- z-z 3-am p_ z me z- z i z-z 3- p--am me o-r z i i z n- p_ -am me o- : z i i z m p-C(=O)NH2 me o-z- z z- z-z -am p- z me o-z- z r z-z -am p- z me o-i z z- z-z 3-am p-C(=O)NHz me o-z- z z- z-z 3- p- z -am me o-i z i z-z n_ p_ z _am me o-i z i z-z eny m--ammo-car oxy is acid o-5U2-Nllz r1 LH2-~'H2-Lri2~l-rnenyi-ammo m- z carboxylic acid o-5Uz-Ntlz t1 Lrlz-~:riz-t,rtzr-pnenyi-armno m- z carboxylic acid o-~Uz-Nriz t m aiz-~aiz-~aizt,ti3-pneny-ammo m-~;(=r~riJmriz carboxylic acid o-JVZ-Nri2 ti LHr~ Hz-~nz ~H3 m-~(=wri)wriz u-Pnenyi ammo carboxylic acid o-JUZ-Ntlz ti l:riz-1;r12-1;ri2tsn-U-pneny m-L(=Nri)Nriz ammo carboxylic acid O-JUZ-NHz ti caiz-caiity rneny-ammo m-~(=U)r~riz q carooxync acid o-z- z i r z -P m- z enY
-~o carboxylic acid O-JUz-Nt12 t1 1:r12-C;riirizr-pnenyl-ammo m- y C;
carboxylic acid o-~UZ-NHz t1 ~:riz-c:r12-(:rtzLri3-pnenyl-ammo m-carboxylic acid o-~Uz-Ntiz ti l:riz-l;riz-c:rizl:rl,-U-pnenyi-ammo m- z carboxylic acid o-~Ui rlz ri trrtz-~tlz-Lrlznn-U-pnenyi-ammo m- z N
carboxylic acid o-z- z z- z-z a m- z y p enoxy-acetic aci ester o-z- z r z-z a m- z y -p enoxyacehc acid ester o-SOz-NHz H C;HZ Hz-CHz Methyl m-C;(=NH)NHz (: l-phenoxy-acehc acid ester O-DUz-Nriz H urirunruriz Memy1 m- z t;li3-pnenoxy-acetic acid ester o-JVz-Nriz tt ~tiz-~:riz-~;tiz Metnyi m-~:~=mrywriz t_;ti3-u-pnenoxy-acetic acid ester O-JVz-Nriz H ~riz-Lnr~-nz nnetnyi m- z nn-u-pnenoxy acetic acid ester o-z- z H CHz-CHz-CHz a m- z y enoxyacehc acid ester o-z- z H CHz-CHz-CHz Methyl m-C;(=U)NHz C1-phenoxyacehc acid ester o-z z - H CHz-CHz-CHz a m- z - y -p enoxyacehc acid ester z z z- z-z a m- z Y
s-p epoxy-acetic acid ester O-SVZ-NHZ H caiz-cai2atz a m- z ~ y -p epoxy acetic acid ester o-SUz-NHz H c:Hz-c:HzWaiz imetny m-~:~=u)mriz tsn-u-pnenoxy acetic acid ester o-z- z z- r z enoxyacehc m- z aci o-z- z z- z-z -p m- z epoxy-acehc aci o-z- z z- z-z -p m-epoxy-acehc aci o-z- z z- z-z 3- p m- z epoxy-acehc aci z- z z- z-2 3- m- )NHz -p epoxy-acehc acid o-z- z z- z-z n- m- z -p epoxy acehc aci o-z- z z- r z enoxyacehc m-C;(=U)NHz aci z- z r z-z -p m- z enoxyacehc aci o-z- z r z-z -p m-C(=O)NHz enoxyacehc aci o-z- z r r z ,-p m- z epoxy-acehc aci o-r z r z-z 3- m--p epoxy acehc acid o-z- z z- r z n- m- z -p epoxy acehc aci o-z- z z- z-z enoxye m-ano o-z- z z- z-z -p m-epoxy-a ano o-z- z z- z-z -p m- z epoxy-a ano o-z- z z z-z s- p m-epoxy-a ano o-z- z z- z-z 3 -p m- z epoxy-a ano o-z- z r r z n- ~(~lHjNHz -p epoxy a ano o-z- z r z z enoxye m- z ano o-r z z- r z -p m- (=O)NHz enoxye ano o-z- z r z-z -p m- z epoxy-a ano o-z- z z- z-z 3 p m- NHz epoxy-a ano r z z- z-z ,- - p epoxy- m-C(=O)NHz a ano o-z- z r z-z n- epoxy- a m- z -p ano o-z- z z- z-z a m-y p epoxy-a y ether o-5uz-NHz H ~tiz-t,tizaiz Memy m-~~=mryvriz ~ m-pnenoxyewy ether O-5V2-NHZ H 1:H2-C;HZ-l;HZ lVleLCly1 m-l.:(=lVt1)lVtlz r-pnenOXy-elllyl ether o-z- z z- z-z a m- z Y
epoxy-ethyl ether o-JVz-NHz ti ~;tiz-~atz-taiz a m- z y -p epoxy-ethyl ether o-~u2 Hz t~ utiz-utiz-t.riz a m- z N y n--p epoxy ethyl ether o-z- z r z- z a m- z y enoxye y ether o-5Uz-NHZ H lalZ-I:HZ Hz Mettlyl m-l: l:l-pnenoxyemyt ether o-SUz-Nriz H 1;H2-1:H2-1:H2 nnetnyi m- z r-pnenoxyemyi ether o-~Vz-NHz H t:rlitiz-~;tiz iviemyl m- z ~; t;n3-phenoxyethyl ether o-SUZ-NHZ H C:HZ-lalzH2 Melllyl m-~:(=V)lVrlz 1; 1:H3 v-phenoxyethyl ether o-SUz-NHz H LHZ HZ tiz Metnyl m-~~=~)wnz ~ ~ tsn-u-phenoxyethylether o-z- z z- s P m- z - enY
o-z- z z- 3 -p m- z - eny o-z- z z- s -p m-C(=NIT)NHz - eny o-z z z- s 3- P m- z ' enY
o-z- z z- 3 s- - P eny m_ -o-z- z z- s n- eny m- z - -p o-r z z- s P m- ~z - enY
o-z- z Z 3 _p m_ - eny o-z- z z- 3 -p m- (=O)NHz - eny --o-z- z r 3 3-P m-C(=O)~z - enY
o-r z z- s s- P eny m_ z - -o-z- z r s n- eny m- NHz - -p o-z z z- 3 m p-C(=NH)NHz - me o-z- z z- s -am p_ z - me z- z 2- g -am p-l.~=lvn)lVn2 - me o-2 2 z- 3 3-am p-C(=NH)NHz _ me 2- 2 z- 3 3- p_ - _am me o-z- z z- s n- p- (=NH)NHz - -am me o-z- z z_ 3 i p~(=O~z - me o-z- z z_ 3 -am p-~:~=~)mnz _ me o-r z z- 3 -am p-C(=O)NHz - me o-z- z z- 3 3-am p-~:(=m)mnz - me o-r z z- 3 3- P_ z - -am me o-i z z- j n- p_ z - -am ' me o-z- z z j eny m-- -ammo-car z oxy is acid o-z- z z- , eny m-C(=NH)NHz _ -ammo carboxylic acid o-z- z z- 3 -p iri~(=NH)NHz _ eny -ammo carboxylic acid o-i z z- s s-P m-~.t=ivn)ivnz - enY
-o carboxylic acid o-~ z z ' carboxylic m ~z ac d ~o o-z- z z- 3 n- m-C(~7I-I)NHz _ _p eny ammo carboxylic acid o-z- z z- 3 eny m~(=O)NHz - -ammo car oxy is acid o-z- z z- 3 -p m-~(=O)NHz - eny -ammo v1 carboxylic acid o-z- z r 3 m-C(=O)NHz -p eny -ammo carboxylic acid o-z- z z- 3 m_C(=O)NHz - ~r11 s-P
enY
-ammo carboxylic acid o-i z r s 3 m-~~=~)wnz - -p eny -ammo carboxylic acid z- z z- s n- m- =O)NHz - _p eny -ammo carboxylic acid o-z- z z- s a m-- y p enoxy-aceric 1i-J
aci ester z- , et m- z J V 11 - ry o-1V z -p z- enoxyacehc acid ester o-r z r s a m-C;(=NH)NHz - y -p epoxy-acetic acid ester o-5Uz-NHz H ~;tiz-Ltil-~;ti3)-a m- z y 3-p epoxy-acetic acid ester o-5Uz-NHZ H Caly-fail-1:ri3)-nnetnymri3-U-pnenoxy- m- z acetic acid ester o-5Uz-NHz H 0.112-l;tll-l:rig)-nnetnyi m- z tsn-v-pnenoxy acetic acid ester o-z- z CHz-CH(-CH3)-Methyl m-C(=U)NHz Phenoxyacehc acid ester o-z- z CHz-CH(-CH3)-Methyl m-C(=U)NHz C1-phenoxyacehc acid ester o-Z z H CHz-CH(-CH3)-Methyllr-phenoxyacehc m- z acid ester o-5Uz riz H c:riz-~til-~ti3)-Mecnyi m- z N ~ri3-pnenoxy-acetic acid ester o-z- z z- s a m- z - Y
;
-p epoxy acetic acid ester o-SUz Hz H c:Hz-cail-Lti3)-a m- z N y n--p epoxy acetic acid ester o-r z z- 3 enoxyacehc m- z - aci o-z- z z- 3 -p m- (--NH)NHz - epoxy-acetic aci o-r z z- 3 -p m-- epoxy-ace c aci o-z- z z- a 3- p m- z - epoxy-acetic aci o-z- z z- 3 ,- -p m-t,l=~ri)mriz - epoxy-ace c acid o-z- z z- 3 n- m- NHz - -p epoxy acetic aci o-z- z z- 3 enoxyacehc m- z - aci o-z- z z- 3 -p m-C(=O)NHz - enoxyacehc aci o-z- z z- 3 -p m-C;(=U)NHz - enoxyacehc aci o-z- z z- a ,- p m-- epoxy-acetic aci o-z- z z- 3 3- -p m- z - epoxy w v,l,l acetic acid o-z- z z- 3 n- m-C(=O)NHz - -p epoxy acetic acW
o-z- z z- 3 enoxye m-- ano o-z z z- 3 -p m- =NH)NHz - epoxy-a ano o-z- z z- 3 -p m- z - epoxy-a ano o-z- z z- 3 3-p m- (=NH)NHz - epoxy-a ano o-z- z i- s 3- m- z - -p epoxy-a ano o-z- z z- 3 n- m- (=NH)NHz - -p epoxy a ano o-z- z z- s enoxye m-~,~=U~mriz - ano o-r z z- 3 -p m- =O)NHz - enoxye ano o-z- z r 3 -p m- z - epoxy-a ano o-r z z- s s- p m- z - epoxy-a ano o-z- z z- j 3- -p epoxy- m-C~ OjlVHz - a ano o-z- z z- 3 n- epoxy- a m-~;l=U)r~riz - -p ano o-z- z z- s a - y v~ my p m- z epoxy-a y ether o-z- z r s a - Y v.~ .w~
-p m-enoxye y ether o-z- z z- , a m- NHz - Y v~ ...y -p epoxy-a y ether o-r z z- s a m- )NHz - Y ,.~ ..
s-p epoxy-ethyl ether o-z- 2 2 3 a m- )NHz - Y ,_,~ ., s--p epoxy-ethyl ether o-z- z r 3 a m- =NH)NHz - y n--p epoxy ethyl ether -o-z- z z- 3 et m- z - y enoxye y ether o-~uz-Nriz z- 3 a m- z - y -p enoxye y ether O-JUz-Ntiz ti ~rii -~ri3l-Memyi m- z ~ry r-pnenoxyecnyi ether o-5Vz tiz n z- a a m- z N - Y
s-phenoxyethyl ether i z r s m-C(=O)NHz - ma ua a ~aa v a Y
n-phenoxyethyl ether o-z- z Me~TSri-~- m-C(=O)NHz ~aa -v..aa ~aa~ ~
z- 3 -phenoxyethyl ether o-z- z r z P m- z - enY
o-z- z z- z -p m-~;l=mtyvriz - eny o-r z z- z -p m-C(=NH)NHz - eny o-z- z z- z r P m-C(=NH)lQHz - enY
o-r z z- z 3- - P eny m~( ~)~z -o-z- z z- z n- eny m-t.;(=mtiyvtiz - -p -o-z- z z' z p m-C(=O)NHZ
- eny o-z- z z- z -p m- z - eny -.
o-z- z z- z -p m-C(=O)NHz - eny~
e-z- z z- z s-P m-C(=OjNHz - enY
r z z- z 3- m- (=O)NH2 - -p eny o-z z r z n- m-~.l=vyvriz - -p eny o-z- z z- z m p- z - me o-i z z- z -am p-C(=NH)NHZ
- me o-z- z r z -am p-~:l=mtiJmtiz - me o-r z z- z 3-am p-C(=NH)NHz - me a- z z z s- p- z - -am me o-z- z z- z n- p- z - -am me e-z- z z- z i p-C(=O)NHz - me o-z- z z- z -am p-~:l=v)ivtiz - me z- z z- Z -am p- z - me o-z- z z- z ,-am p-t:l=vyvriz - me z- z z- z 3 p- (=O)NHz - -am me z- z z- z n- p-C(=O)NHz - -am me z- z z- z eny m-~.~=mryvriz - -ammo-car oxy is acid o-z z z- z eny m-C(=NH)NHz - -ammo w.a a as a carboxylic acid o-z z z- z -p m-C(=~I)NHz - eny -ammo a-as a carboxylic acid o-z z z- z m-C(=NH)NHz - v..aa as a 3-p eny -ammo carboxylic acid o-z- z z- z 3- m- z - -p eny ammo carboxylic acid o-z- z z- z n- m- (=NH)NHz - -p eny ammo carboxylic acid o-z- z z- z eny m- z - -ammo car oxy is acid O-JUZ-Nriz ti uriz-ury-Nriz~-m-pnenyi-ammo m-~l=v~Nriz carboxylic acid O-JVZ tiz r~ uriz-pry-Nriz~-r-pnenyi-ammo m-~l=vyvriz N
carboxylic acid o-~u2 tiz m ;riz-~:ry-mtiz~-~;ti3-pnenyi-ammo m-~;l=vyvriz N
carboxylic acid o-~uz-Ntiz r~ uriz-ury-Nriz~-~ri3-u-pneny-ammo m-~l=~Jwriz carboxylic acid O-JVZ riz t m ;riz-~:ry-Ntiz~-nn-v-pneny-ammo m-~:l=vyvriz N
carboxylic acid r z z- z a m- z - y p enoxy-acetic aci ester o- z- z z- z - a m- z Y
-p enoxyacehc acid ester o-SOz-NHz H CHz CH(-NHz)-Methyl m-C(=NH)NHz l~'-phenoxy-acetic acid ester o-auz-Ntiz tt ~tiz-pry-tvtiz)-Merry m-~~=wri)wriz ~ri3-pnenoxy-acetic acid ester o-~uz Ntiz ti ~ri2-pry-Nriz)-Memyi m-~(=wri)wriz ~ri3-u-pnenoxy-acetic acid ester o-~Vz-Nriz ti ~tiz-Sri(-Ntiz)-Memyi m- z tsn-u-pnenoxy acetic acid ester o-S~2-NHz H CHz CH(-NHz)-Methyl m- z Yhenoxyacehc acid ester o- z- z H CHz CH(-NHz)-a m- z y -p enoxyacehc acid ester o- z- z -- H CHi CH(-NHz)-a m- z y -p enoxyacehc acid ester o-5uz-NHZ H l;Hz-lai(-1Vt12)-a m-y 3-p erioxy-acetic acid ester O-5uz-NHz H LHz LH~-Ntiz)-Metnyi m- z ~ti3-u-pnenoxy acetic acid ester o-5uz-NHZ H (:Hi C:H~-Ntlz)-Metnyl m-tin-u-prieriOXy acetic acid ester o- z- z z- z - enoxyace m- z c aci o- z- z z- z - -p m-C(=NFI)NHZ
epoxy-acetic aci o- z- z z- z - -p m- )NHz epoxy-acetic aci o- r z z z - 3- p m-C(=NH)NHz epoxy-acetic aci o- z- z z- z - 3- m- z -p epoxy-acetic acid o- z- z z- z - n- m- z -p epoxy acetic aci o- z- z z- z - enoxyacehc m- (=O)NHz aci o- r z z- z - -p m-C(=U)NHz enoxyacehc aci o- z- z z- z - -p m- .(=~NH2 enoxyacehc aci o- z- z r z - 3- p m- z epoxy-acetic aci o- z z z- z - 3- m- (=O)NH2 -p epoxy acetic acid o- z- z z- z - n- m- (--~NHZ
-p epoxy acetic aci o- z- z z- z - enoxye m- (=PHjNHz ano o- z- z z- z - -p m-~;~=ivri)ivriz epoxy-a ano o- z- z z- z - -p m- (=NH)NHz epoxy-a ano o- z- z z- z - 3- p m- z epoxy-a ano o- z- z z- z - s- - p epoxy-a m- NHz ano o- z- z z- z - n- epoxy a m- z -p ano o- z- z z- z - enoxye m- z ano o- z- z z- z - -p m-~;~=u)ivriz enoxye ano o- z- z r z - -p m- (=~)NHz epoxy-a ano o- z- z z- z - j p m- z , epoxy-a ano o- z- z z- z - s- - p epoxy- m- z a ano o- z z z- z - n_ epoxy- a m_ _p ano o- z- z z- z - a Y y myw p m-epoxy-a y ether o- r z z- z - a m- z Y
-p enoxye y ether o-JVz-Nriz H ~tiz-qty-Ntiz)-Merry m-~~=wri)wriz r-pnenoxy-emyi ether o-~Vz-Nriz tt ~riz-cay-Ntiz)-nnemyi m- z ~ri3-pnenoxy-ethyl ether o-~uz NHz tm atz-Lty-mtiz)-memym;ri3-u-pnenoxy- m-~~=mri)mnz ethyl ether o-5uz-NHz ti ~nz-~ril-Nnz)-Merry m-~~=wri)mriz tsn-u-pnenoxy ethyl ether -o-z- z z- z et m- z - y enoxye y ether O-JUz-Nriz l 2 a m- z - y -p enoxye y ether _ - z a rn=C(=O)NHz as _ y _phenoxyethyl-ava w a n-ether o-z- z z_ z a m- )NHz - y w.~ v 3__ ma ua m.aa phenoxyethyl ether _ _ CHz_ ~ a m-C(=O)NHz y phenoxyethyl ether O-JUz-Ntiz ri ~riz-Sri(-wriz)-Memyi m-~;l=a nn-u- yvtiz phenoxyethyl ether o-z- z r n p m- z - enY
o-z- z z - -p m-~l=mri~wriz n eny -o-z- z z- _ -p m- z n eny _ --o-z- z z- - ~: m- (=~)~z n 3-phenyl -o-r z z- - 3 p eny m-C(=~~z n --o-z- z z- - n_ eny m- z n _p -o-z- z z- - p m- =O)~z n eny -o-r z z- _ -p m- z n eny _ o-z- z 2 - -p m- z n eny -o-r z z- - 3- p m_ -O)NHZ
n eny -o-r z z- - 3_ _ p eny m- z n -o-z- z z- - n_ eny m- z n _p _ -o-z- z z - me p- z n -o-r z z- _ -am p_ =NH)NHz n me _ o-z- z z- _ -am p- z n me _ o-z- z z - 3-am p=CC ~~z n me -o-z- z l - 3- p- z n -am - me o-r z z- - n_ p- )NHz n _am - me o-z- z z- - m p-C(=O)NHz n me -o-z- z Z - -am p- z n me -o-z- z z- _ -am p_ =O)~2 n me _ o-z- z z- - 3-am p- z n me -o-r z z- - 3_ p_ =O)NHz n _~
- me o-z- z z- - n_ p- z n _am - me o-z- z Z - eny m- (=NH)NHz n -ammo-car - oxy is acid o-~u2 riz ti ~riz-~ry-~snlw;i-rneny-ammo m-~l=wryvriz w carboxylic acid O-JUz-Ntiz m aiz-pail-nn~-r-pnenyi-armno m-~;l=mryvriz carboxylic acid z- 2 2- ' 3-p m- z n eny - -ammo carboxylic acid o-~uz-Ntiz ti ~riz-aril-~snl-~rij-u-pnenyi m-~l=ivrilwriz ammo carboxylic acid O-JVZ-Nri2 t m aiz-Ltil-tsn~-tsn-u-pnenyi m-~:l=mryvriz ammo carboxylic acid o-JVz-Nri2 t-~ z - eny m- z n -ammo - car oxy is acid O-JVZ-lVri2 z- _ -p y -ammo m- z n en _ carboxy lic acid o-~u2 tiz t-~ ~riz-qty-tsn~-r-pnenyi-ammo m-~l=u~wriz N
carboxylic acid O-JVz riz t~ ~riz-t,ril-tsn~-t_;ri3-pneny-ammo m-~:l=uyvriz N
carboxylic acid O-JUZ ttz ri z- n 3 m- z w - -p eny -ammo carboxylic acid -o-z z CHz-CH(~n~-~n=O-p~amW m-C(_O)~z o carboxylic acid o-z- z z- - a m- z n y - p enoxy-acetic aci ester o-SUz-NHz z- - n - a m- z ry -p enoxyacehc acid ester o-SUz-NHz H CHz-CH(-Bn)-Methyl m- z r-phenoxy-acetic acid ester o-1Vz-Ntlz ti lalz-fall-tSn)-Merry m-ul=wriJwriz ~ri3-pnenoxy-acetic acid ester o-JVz-Ntlz H lily-fall-tSn)-MeLllyl m- z 1.ri3 u-pnenOXy-acetic acid ester O-JVz-Nriz H Ltiz-Ltil-tsnJ-a m- z y n_ -p epoxy acetic acid ester o-SOz-NHz H CHz-CH(-Bn)-Methyl m- z Yhenoxyacehc acid ester o-SOz-NHz H CHz-CH(-Bn)-Methyl m-C(=U)NHz C1-phenoxyacehc acid ester o-SOz-NHz H CHz-CH(-Bn)-Methyl m-C(=U)NHz r'-phenoxyacehc acid ester O-JUz-wHz H ~riz-aril-tsnJ-enemy m-~l=uJwriz ~ri3-pnenoxy-acetic acid ester O-JVZ wHz ti ~riz-aril-tsnJ-nnemyi m-~l=uJwriz uri,-u-pnenoxy acetic acid ester O-JVZ Ntiz ti ~tiz ~ty-rsnJ-Merry m-~,l=vJivriz tsn-u-pnenoxy acetic acid ester o- z- z z- - n - enoxyacehc m- z aci o- z- z z- - n - -p m-C(=NH)NHz epoxy-acetic aci o- r z r - n - -p m- z epoxy-acetic aci o- z- z z (->3n)= CH3-pherioXy-acetic m-C(=NH)NHz acid o- z- z z- - n - 3- m-C(=NH)NHz -p epoxy-acetic acid o- z- z z- - n - n- m- z -p epoxy acetic aci o- z- z z- - n - enoxyacehc m-aci -o- z- z z- - n - -p m- z enoxyacehc aci o- z- z z- - n - -p m-C(=O)NHz enoXyacehc act o- z- z z- - n - j m- z p epoxy-acetic aci o- z- z z- - n - 3- m- (=O)NHz -p epoxy acetic acid o- z- z z- - n - n- m- z -p epoxy acetic aci o- z- z z- - n - enoxye m- z ano o- z- z z- - n - -p m-C(=NH)NHz epoxy-a anol o- z- z z- - n - -p m- z epoxy-a ano o- i z z- - n - s- p m-epoxy-a ano o- z- z r - n - 3- _ p epoxy-a m- z ano o- z- z z - n - n- epoxy a m- z -p ano o- z- 2 z- - n - enoxye m-~l=uJwriz ano o- z- z 2 - n - -p m- z enoxye ano o- z- z z- - n - -p m-~-- NHz epoxy-a anol -o- z- z z- - n - s- P m- z epoxy-a ano o- i z z- - n - 3_ _ p epoxy- m-~:l=uJivriz a ano o- z- z 2 - n - n- epoxy- a m- z -p ano o- r z z- -Bn)- ~~p~enoXy-ethyl m=C( NH)NHz ether ~'JVz lVttz z- - n - a m- z y -p enoxye y ether o_JVz'lvriz 2 - n - a m- z y -p epoxy-a y ether o-~uz-Nriz r~ z - n - a m- z y s-p epoxy-ethyl ether o- ~ z H 2 - n - et m-C(=NH)NHz y -p epoxy-ethyl ether o-~uz-wriz rm :riz-~:ry-rsnJ-Merry m-~l=ivriJivriz rsn-v-pnenoxy ethyl ether o-z- z Z- - n a m- z - y enoxye ry ether o-~uz-Ntlz tl ~tlz-gall-tsn)-lvlemyl;l-pnenoxyemyl m-~,(=v)lvrlz ether O-JVz-Nrlz ri l:riz-l;rll-lin)-Nlelllyl m- z r-prienOXyeUlyl ether o-JVz-Nliz z- - n a m- z - Y
a-phenoxyethyl ether o-JVz-Ntlz r1 ~rlz-~rll-lsn)-l vlemyl ~r13-u- m- z phenoxyethyl ether o-JVz-Nrlz r1 urlz-Vrll-lsn)-l vlemyllsn-u- m- z phenoxyethyl ether O-JUz-Nriz n calz-fall-~alz-p m- z eny COOCH3)-O-JUz-Nriz tl z- z- -p m- z eny COOCH,)-O-5Vz-Nriz tl cali :rlz-r-pnenyl m-~:(=Nrl)lvrlz Ltll-~
COOCHj)-o-5Vz-Nriz z- z- 3-p m- z eny COOCH3)-O-JUz-Ntlz ti C;tiz itiz-3- m- z fall-l -p eriy COOCH,)-O-JUz-Nriz ri ~riz-aril-~riz-n_ m- z -p eny COOCH3)-O-JUz-Nriz tl ~riz-~rll-~rlz-pnenyl m-~l=v)lvrlz COOCH,)-O-JUz-Nrl2 ti l:rlz-fall-lalz-t_;1-prienyl m-~:l=v)lVrlz COOCH3)-o-z- z i z- -p m- z eny COOCH3)-o-~uz tlz tt alz-gall-~tlz-~;t13=pnenyl m-~:(=u)lvrlz N
COOCH3)-o-~u2 tiz z z- s- m- z N -P
eny COOCH,)-o-~u2 tlz z- z- n- m- z N -p eny COOCH,)-o-~Uz-Ntiz z- z- m p- i me COOCH,)-o-~u2 rlz z- z- -am p- z N me COOCH,)-o-~u2 rlz z z- -am p- z N me COOCH3)-z 2 z- s-am P- z me COOCH,)-o-JUz-Nriz rl l:rlz ;tiz-j_ ~p- z fail-l _am me COOCH3)-o-~u2 tlz rl ~r12 rlzrsn-u-anllme p- z N ~rll-~
COOCH3)-O-JVz-Nriz ~;tlz alz-m p- z t~tll-~ me COOCH3)-.
o-aVz tlz rl ~rlz rlz-~l-anllme p-~l=~)lvrlz N aril-~
COOCH3)-o-~uz ttz rl ~rlz-~rll-~rlz-r-anllme p-~l=u)lvrlz N
COOCH,)-O-JVZ-lvriz ri ~riz-tall-~riz-~:r13-anlnne p-~:(=v)lvrlz COOCH,)-O-JUz-Ntiz n l:ri2lall-l;tiy-lalg-V-an111I1e p-l.l=V)Nrlz COOCH3)-o-r z r z- n- p- z -and me COOCH,)-o-~Vz-Ntlz ri Lnz-Lnl-~riz-rnenyl-amino-carooxync m-~:l=Ntl)lvtlz COOCH,)- acid o- r z z- z- eny -ammo ..,~ .wy..
m- z COOCH3)- carboxylic acid o- z- z z- z- -p m-~(=rVryr~riz eny -ammo COOCH,)- carboxylic acid o-SUZ NHz r1 Ltiz-Lti(-Ltiz-LH3-pnenyi-ammo m-~(=~ryr~riz COOCH3)- carboxylic acid O-JUz-Ntiz t~ ~riZ ~;ri(-~riz-~ti3 m-~(=mry~riz u-pnenyi ammo COOCH3)- carboxylic acid O-JUz-Ntiz t~ ~riz-Sri(-~riz-~sn-u-pnenyi m-~(=wti~mriz ammo COOCH3)- carboxylic acid o-aV2 NHz ri ~tiz-Sri(-~riz-rnenyi-ammo m- z carooxyiic COOCH3)- acid o-~UZ NHz ti z- z- -p y -ammo m- z en COOCH3)- carboxylic acid o-~Vz NHz H ~alz-~a1(-~;tlz-r-pnenyl-ammo m-t.(=u)rVriz COOCH3)- carboxylic acid o-JVz NHz W a1z-Lt1(-~;tlz3 m- z P
enY
-ammo COOCH3)- carboxylic acid o-~Uz-NHz W ;tlz-~t1(-~;ttZ3 m- z -p eny -ammo COOCH,)- carboxylic acid o-JU2-Ntl2 t1 lalz-l;tl(-1;112-n_ m- z -p eny -ammo COOCH3)- carboxylic acid o- z- 2 H CHz-CH(-CHz-a m- z y p enoxy-acehc COOCH3)- acid ester o- 2-NHz H CHz-CH(-CHz-Methyl m-C;(=NH)NHz C;1-phenoxyacehc COOCH3)- acid ester o-SUz-NHz H CHz-CH(-CHz-Methyl m- z t'-phenoxy-acehc COOCH;)- acid ester o-JUZ-Nriz m ;tiz-jai(-taiz-nnewym:ri3-pnenoxy- m-~~=mry~riz COOCH3)- acetic acid ester o-SOz-NHz H CHz-CH(-(:HZMethyl m-(:(=NH)NHz (:H3-U-phenoxy-COOCH3)- acetic acid ester o-~uz NHz ti Ltiz ~ty-~ry-Merry m-~(=wrywriz tsn-u-pnenoxy COOCH3)- acetic acid ester o-SUz-NHz H (:Hz-C:H(-(:Hz-Methyl m-C;(=U)NHz Yhenoxyacehc COOCH,)- acid ester o-SOz-NHz H C;Hz-(:H(-C;HZMethyl m- z (:1-phenoxyacehc COOCH,)- acid ester o-SOz-NHz H CHz-CH(-(:Hza m- z y -p enoxyacehc COOCH3)- acid ester o-~uz-Ntiz tW a~z-~a~(-tatz-a m- z y s-p epoxy-COOCH3)- acetic acid ester O-JUz-Ntiz ri ~;riz-Sri(-~:riz-a m- z Y
-p epoxy COOCH3)- acetic acid ester O-JVZ-Nriy m ;tiz-Sri(-~aiz-Memyi m- z tsn-u-pnenoxy COOCH3)- acetic acid ester o-SOz-NHz H C;Hz-(:H(-C;Hz-enoxyacehc m- z aci COOCH3)-o- z- z z- r -p m- z epoxy-acehc aci COOCH3)-o-SUz-NHz H C;Hz-(:H(-C;Hz-r-phenoxy- m-C:(=NH)NHz acehc acid COOCH,)-o-SUz NHz H C:Hz-(:H(-C;Hz-(:H3-phenoxy-acehc m- z acid COOCH3)-o-SU2 NHz H C;Hz-C;H(-(;Hz-(:H3-U-phenoxy-acehc m-(:(=NH)NHz COOCH,)- acid o-SOz NHz H C:Hz-C:H(-C:Hz-Bn-U-phenoxy m-C:(=NH)NHz acehc acid COOCH3)-o-SUz-NHz H (:Hz-(rH(-(:Hz-Yhenoxyacehc m-(:(=U)NHz acid COOCH3)-o- z- z r z- -p m- z enoxyacehc aci COOCH3)-z r r -p m-(:(=U)NHz J V enoxyacehc o-z- aci COOCH3)-o-SOz-NHz H (:Hz-C;H(-C;HZ C:H3-phenoxy-acetic m-C;(=U)NHz acid COOCH,)-o-2-NHz H z- z-3 m- z J V -p enoxy acetic COOCH,)- acid o-z-NHz H (:Hz-CH(-CHz-Bn-O-phenoxy m-C;(=U)NHz acetic acid COOCH,)-o-~urNHz H t.;Hz-LHlw;tirrnenoxyemanoi m-~l=wryrrriz COOCH,)-o-~u2-NHZ H MHz-~ry-~riz-~i-pnenoxy-emanoi m-~l=wri)ivriz COOCH,)-o-z Z z z--p m-enoxy-a ano COOCH3)-o-~u~ Hz H z- z-,-p m- z N enoxy-a ano COOCH,)-o-~u2 Hz ti LHz-~Hl-LHr ~ris-~-Pnenoxy-emanoi m-N
COOCH3)-o-SOz-NHz H (:Hz-C;H(-(:Hz-Bn-U-phenoxy m- z ethanol COOCH3)-O-JUZ-Nriz H lalz-l;ril-l;tiz-enoxye m-ano COOCH3)-O-~VZ-NHZ ti z z--p m- z enoxye ano COOCH,)-O-JVZ-NHz r1 t,Hz iz-r-pnenoxy-emanoi m-~:l=uyvriz ~;Hl-Lt COOCH,)-O-JVZ-Nri2 z- z-3 m-P
enoxy-a ano COOCH3)-o-5Uz Hz r z-3- m- z N -p enoxy-a ano COOCH,)-o-5Uz Hz H c:H2 z-tsn-u-pnenoxy- m-~:l=~yvriz N c:Hl-c:H emanoi COOCH3)-o-SUz-NHz H z- z-a m- z Y
P
enoxy-a y COOCH3)- ether o-5uz-NHz t1 c,H2 iz-metny m-t,l=mriyvriz c:Hl-ca m-pnenoxyetnyi COOCH3)- ether o-5u2 tiz H ~Hz-~til-~tiz-Mecnyi m-~l=mriyvriz N r-pnenoxy-emyi COOCH3)- ether O-5u2-NHz H cai2-LHl-LHz-Mewyl m-~ri3-pnenoxy-COOCH3)- ethyl ether O-5u2-NHZ H LHZ-LHl-LHz 1\netnyl m-~;l=rrryrrriz ~ti3-u-pnenoxy-COOCH3)- ethyl ether o-JVz Hz ti LH2-t.Hl-~aiz-Memyi m-N nn-u-pnenoxy COOCH3)- ethyl ether O-JVz-Nri2 t1 lal2 iz-nnemyi m- z ~;tilw;t rnenoxyemyi COOCH3)- ether O-JV2-Nt12 m ai? Ltil-taiz-nnemym;i-pnenoxyemyi m- z COOCH3)- ether o-JVz Hz H c:Hz-pail-~aiz-a m- z N y -p enoxye y COOCH3)- ether o-~uz-NHZ n ~riz-aril-~ri2a m- z y COOCH3)- phenoxyethyl ether O-JUZ-NHZ H 1;H2-l:H(-l;Hz a y 3- m-COOCH3)- phenoxyethyl ether o-JUZ-NHZ H l:Hz-Citl(-la12-l Vlemyl, tan-V- m-l~l=V)lVri2 COOCH3)- phenoxyethyl ether o-JUz-NHz H (:Hz-Ltll-t,tiz-pnenyl m-~l=mri)mriz CHZ-OH)-O-JUZ-NHZ ti 1,r12-fail-1x12-lLl-pnenyl m-l.l=lVr1)1vr12 CHZ-OH)-O-JVZ-NHz ri t_;tiz-aril-taiz-r-pnenyi m- z CHz OH)-z- z- z UV 111 11 v11 11 o- r z 3-p enY~
CHz-OH)-O-JVZ Nriz ri l:riz-l:ri(-l:tiZl:ri3-u-pnenyi m-~(=~riJNriz CHz-OH)-o_ z- z ri z- z- ri_ _p eny m- z CHz-OH)-o-~uz-Nriz rm :riz-l:ri(-l:riz-pneny m-~;(=u~~riz CHz-OH)-O-JUz-Nriz ri l:nz-l:ri(-c:riz_-p eny m- z CHz-OH)-o-~uz-Ntiz z- z- -p eny m- z CHz-OH)-O-JUz-Nriz 2- z- ,-p eny m- z CHz-OH)-O-JUZ-Nti2 H lily-lJtl(-l=t12-lJri3-u-pnenyi m-~(=vyvriz CHz OH)-O-JV2-Ntlz t1 1a12-lal(-1;11z-tSn-u-pnenyl m-l;(=V)Nrl2 CHz-OH)-O-JVZ Ntiz t1 1x12-l:ri(-1;ri2-Amlllle p-CHz-OH)-O-JVZ-Ntiz ri 1.r12-l:rl(-1x12-l.l-anllme p-l.(=lVt1)iVri~
CHz-OH)-O-lV2-NtlZ t1 l;tl2-l:ri(-lalz-r-anlllrie p-l;(=lVr1)Nriz CHZ OH)-O-JUZ-Ntl2 t1 1:ri2-l:ri(-l;tiz-lai3-amlme p-CHz-OH)-o-~VZ-Nriz ri laiz-Cai(-1.:t12-3- -aril me p-CHz-OH)-o-5Uz-Nriz ri z_ z_ n_ _yne p- z CHz-OH)-o-5Vz-Nriz ti l:riz-cai(-c.;tlz-amlme p-l:(=u~~ri2 CHz-OH)-o-5Uz Nliz z- z- -am me p- z CHz-OH)-O-5Vz-NHz Z- Z- -am me p-CHz-OH)-o-5U2 Ntlz H Ltiz-Cai(-laiz-1x13-amlme p-l:(=u)mriz CHz-OH)-O-JU2-Ntl2 H l;riz-l;ri(-1x12-3- -am me p-CHz OH)-o-JUz-Ntiz H l:tiz-lai(-laiz-n_ _am me p- z CHz-OH)-o-~UZ Ntiz ti calz-cal(-lalzrnenyi-ammo-caruoxyncm- z CHz OH)- acid O-JUZ-Ntlz H lalz-l,ti(-1,t12-l.l-Ynenyl-ammo m-l.(=lVr1)1Vr12 CHz-OH)- carboxylic acid O-~Uz-Ntiz tt l:nz l:ri(-l~riZ-r-pnenyi-ammo m-l:(=wry~riz CHz-OH)- carboxylic acid o-JU2-NHZ ri lalz-l:tl(-1x12-1;r13-pnenyl-ammom-l.(=Wri~lVriz CHz-OH)- carboxylic acid o-lU2-NHZ t1 1a12-l:ri(-lily-l;rlj-u-pnenyl m-l:(=LVri)lVrlz ammo CHz-OH)- carboxylic acid O-JUZ-NHz t~ cai2 Sri(-c:riz-tsn-u-pnenyi m-~(=wryrrriz ammo CHz OH)- carboxylic acid O-JUZ-Ntl2 ti laiz-l;ri(-layrnenyi-ammo carnoxyncm-l:(=uJNriz CHz-OH)- acid o-wz-Ntiz r~ l:riz-l:ri(-c:riz-l:upneny-ammo m- z CHz-OH)- carboxylic acid o-5uz-Ntiz n l:riz-l:ri(-caiz-r-pnenyi-ammo m- z CHz-OH)- carboxylic acid o-~uz-Ntiz t~ laiz-l:ri(-laiz-l:ri3-pnenyi-ammom-l:(=u~rrriz CHz OH)- carboxylic acid o-S02 NHz H z- z- 3- -p ieny -ammom- z ~.,.. ..~.~-....
CHz-OH)- carboxylic acid O-JVZ-lVtiz t1 1a12-l;H(-C:HZ-tiri-U-prienyi-ammom-C:(=V)NHZ
CHz-OH)- carboxylic acid o-JVz-Nriz H C:Hz-(:H(-(:Hz-Methyl phenoxy-aceticm-(:(=NH)NHz CHz-OH)- acid ester o-5Uz-NHz (:Hz-(:H(-(:Hz-Methyl (:1-phenoxyacehcm-(:(=NH)NHz CHz-OH)- acid ester o-5Uz-NHz C;Hz-(:H(-(:Hz-Methyl 1~'-phenoxy-m-C;(=NH)NHz acetic CHz-OH)- acid ester o- z- z z- z- a Y 3 p epoxy- m- z CHz-OH)- acetic acid ester O-~VZ-irriz ri ~:riZ aril-~riz-nnemyi ~ri3-u-pnenoxy-m-~:l=Nrywriz CHz-OH)- acetic acid ester o- z- z z- z- a y n- -p epoxy m- z CHz-OH)- acetic acid ester o-SUz-NHz r z- a y enoxyacehc m- z CHz-OH)- acid ester o-SUz NHz H (:Hz-(:H(-(:Hz-Methyl C:1-phenoxyacehcm-(:(=U)NHz CHz-OH)- acid ester o-SOz NHz H CHz-C;H(-C:Hz-Methyl F-phenoxyaceticm-C(=O)NHz CHz-OH)- acid ester O-JV2-lVtlz ri 1.ri2-lal(-1:ri2-Metnym:ri3-pnenoxy-m-t,(=u~Ntiz CHz-OH)- acetic acid ester O-JUz-ivriz ri ~riz-Sri(-~riz-ivieuiyi ~ri3-u-pnenoxym-~l=u)irriz CHz-OH)- acetic acid ester o-~uz Nriz ri uriz-~ry-~rizimeciiyi tsn-v-pnenoxym-~l=u)ivriz CHz-OH)- acetic acid ester o-SUZ NHz H (:Hz-C;H(-(:Hz-Yhenoxyacehc m-(:(=NH)NHz acid CHz-OH)-o-SOz-NHz H C;Hz-C;H(-(:Hz-C;1-phenoxy-aceticm-(:(=NH)NHz acid CHz-OH)-o-SOz-NHz H C;HZ (:H(-(:Hz--p epoxy- aceticm- z aci CHz OH)-o-SOz-NHz H C:Hz-(:H(-(:Hz-3-p epoxy-aceticm- z aci CHz OH)-o-SOz-NHz H C;Hz-C;H(-(:Hz-3- -p epoxy-aceticm- z CHz-OH)- acid o-SOz-NHz z- r ri- -p epoxy m- z acetic aci CHz-OH)-o- z- z r z- enoxyacetic aci m- z CHz-OH)-o-SOZ NHz H CHz-(:H(-C:Hz-C;1-phenoxyacehcm-C;(=U)NHz acid CHz-OH)-o-SOz-NHz H CHz-C:H(-C;Hz--p enoxyacehc m- z aci CHz-OH)-o-SOz-NHz H z- z 3-p epoxy-aceticm- z aci CHz-OH)-o-SOz-NHz H z- r s- -p epoxy aceticm- z CHz OH)- acid o-SOz NHz H (:Hz-(:H(-C;Hz-13n-U-phenoxy m-C;(=U)NHz acetic acid CHz-OH)-O-JVz-Nriz ri ~riz-aril-~riz-rnenoxyemanoi m-~l=ivri)Nriz CHz-OH)-O-JUz-Nriz ri ~riz-Sri(-~riz-~i-pnenoxy-emanoim-~l=ivri)~riz CHz-OH)-o-au2 NHz H ~tiz-~til-~;HZ-r-pnenoxy- etnanoim-~l=ivri)ivriz CHz-OH)-O-JVz-lVHz H 1;t12-l;ril-1a12-1;t13-prienOXy-elllanoim-l;(=lVt1)lVri2 CHz-OH)-o-~uz-ivHz ti r z- s- -p epoxy-a m- z ano CHz-OH)-- -H m- z JV 111 W 1 ~r11'-WL V 11 11 1 o- r z 1 n- -p epoxy et z- z- ano CHz-OH)-o-'uz-wriz r~ ~-riz-Lril-Lnrrnenoxyetnanoi m-~:l=uyvtiz CHz-OH)-O-JUZ writ ri ~riz-aril-~riz-m-pnenoxyemanoi m-~l=u~wriz CHz-OH)-O-JUZ-wriz ri ~riz-~:ril-t;tiz-r-pnenoxy-emanoim-~l=u~wtiz CHz-OH)-O-JUZ-writ ri ~nz-~nl-~-riz-~n3-pnenoxy-emanoim-~l=uJwriz CHz-OH)-O-JVz wriz r~ ~nz-~-nl-~-riz-~ri3-u-pnenoxy- m-ul=u~wriz emanoi CHZ OH)-o-~uz-wtiz z- r n- -p epoxy- m- z a ano CHz-OH)-o-wz-wriz m aiz-tJril-t,ry-memyi pnenoxy-etnyim-t,l=wrywriz CHz-OH)- ether o-~u2 wriz r z- a y -p enoxye m- z y CHz-OH)- ether o-auz-wriz z- z- a y -p epoxy-a m- z y CHz-OH)- ether o-JVz-writ Y r a Y s-p epoxy- m- z CHz-OH)- ethyl ether o-auz-wtiz m aiz-~;til-~aiz-Metnymai3-v-pnenoxy-m-~;l=wrywriz CHz-OH)- ethyl ether o-5uz wtiz t~ uttz-aril-uriz-enemy ~sn-v-pnenoxym- z CHz-OH)- ethyl ether o- Uz z r z- a y enoxye y m- z CHz-OH)- ether o-~uz wtiz m :ti? ~ailwaiz-nnetnyi m-pnenoxyemyim-~:l=~~wriz CHz-OH)- ether o-auz writ ri ~riz aril-~tiz-Memyi r-pnenoxyemyim-~l=u~wriz CHz-OH)- ether o-auz-wtiz ti tJtiz-~til-~aizMecny ~ti3- m- z CHz-OH)- phenoxyethyl ether o-~uz-wtiz t-~ uriz-aril-uriz-nnemyi urij-u- m-t,l=vlwriz CHz-OH)- phenoxyethyl ether o-~uz-wtiz t-~ uriz-aril-utiz-nnetnyi nn-v- m-~l=a yvriz CHz-OH)- phenoxyethyl ether o-~uz wtiz ti ~riz-~ril-~riz-pnenyi m-~l=mryvnz C(=O)-N-morpholino)-o-'uz-wtiz tm aiz-tail-~;tiz-~a-pneny m-~,l=wrywriz C(=O)-N-morpholino)-o-5uz-wtiz ti Lttz-~til-~tiz-r-pnenyi m-~l=wrywriz C(=O)-N-morpholino)-O-JVZ-wriz t~ t_;ttz-pail-~;ti2-~ai3-pnenyi m-i.l=mrtyvriz C(=O)-N-morpholino)-O-JVZ-wtiz tm aiz-Ltil-taiz-~;ri,-u-pnenyi m-~:l=mryvnz C(=O)-N-morpholino)-O-JVZ-wtl2 ti ~riz-~til-~riz-tsn-u-pnenyi m-~l=wriJwri2 C(=O)-N-morpholino)-O-JUz-wriz ri taiz-aril-~:riz-pnenyt m-~l=vyvriz C(-0)-N-morpholino)-O-JVZ-wriz t~ uriz-~til-uriz-m-pnenyi m-~l=v~wriz C(=O)-N-morpholino)-o- z H ~z-~ z- -p eny m-C(=O)-N-morpholino)-O-JUZ-lvriz ri ~riz-aril-~riz-trti3-pnenyl m-~:l=u)lrriz C(=O)-N-morpholino)-o-~uz-lvrlz ri ~rlz-aril-~rlz~r13-u-pnenyl m-~l=u)lrriz C(=O)-N-molpholino)-O-JUZ-ivriz ri t,riz-~;ril-~riz-rsn-u-pnenyl m-~:l=u)lVrlz C(=O)-N-morpholino)-O-JUz Nriz n ~riz aril-~riz-Anllme p-ul=lrri)lVrlz C(=O)-N-morpholino)-O-JUZ-lvriz n ~rlz-~rll-~rlz-~l-anllme p-~l=lrri)lrrlz C(=O)-N-morpholino)-O-JUz-lvriz n urlz aril-url2-r-anllme p-~l=lrri)lVrlz C(=O)-N-morpholino)-O-JUz-lvriz ri ~riZ ~til-~riz-~r13-amllne p-~l=lrti)lrriz C(=O)-N-morpholino)-o-auz-lvriz r1 urlz-unl-uriz-un3-u-amlme p-~l=lVri)rirlz C(=O)-N-morpholino)-O-JU2-1Vt12 H 1x12-l:rll-l=ri2-rsn-u-anllme p-~.l=mri)lrriz C(=O)-N-morpholino)-o-~uz-Nriz n uriz ~:ril-~riz-Amlme p-~l=u)lrriz C(=O)-N-morpholino)-o-~uz Ntiz ti aiz-~:ril-~aiz-~l-anllme p-~l=u)mriz C(=O)-N-morpholino)-o-~uz lvriz n ~riz ~;rll-~rlz-r-anllme p-~l=u)lrtiz C(=O)-N-morpholino)-O-JUz luriz n uriz aril-~riz-~ti3-amlme p-~l=u)lrriz C(=O)-N-morpholino)-o-au2lvtiz n urlz-aril-uriz-~r13-u-amlme p-~l=u)lvriz C(=O)-N-morpholino)-O-JU2-Nriz ti l:riz l;ril-lain-tfri-u-anllllle p-l;l=u)lVri2 C(=O)-N-morpholino)-O-JUz 1Vt12 ti l~rlz-l:rll-1;r12-Ynenyl-amino-CarDOXyIICm-l:l=lVt1)iVrl2 C(=O)-N- acid morpholino)-O-JUZ-lvriz ri trtlZ ~;ril-~:riz-~;1-rnenyl-aminom-~l=lxri)lrriz C(=O)-N- carboxylic acid morpholino)-o-~uz lurlz ti url2 ~;ril-~riz-r-pnenyl-amino m-~l=lrrl)lrriz C(=O)-N- carboxylic acid morpholino)-o-~u2lvtlz rl ~rlz-~rll-~rlz~ri3-pnenyl-ammom-~l=lrri)lrriz C(=O)-N- carboxylic acid morpholino)-O-~uz-Nriz ri c:riz-aril-~riz~ti,-u-pnenyl m-ammo C(=O)-N- carboxylic acid more o mo -o-SOz-NHz H - - z- n_ _p eny ammo m- z C(=O)-N- carboxylic acid morpholino)-o-wz-mriz n ~nz-~ril-~nz-rneny-ammo carooxyncm-~l=uyvriz C(=O)-N- acid morpholino)-O-~uz-mriz ri ~.riz-~:ri(-~riz-~;i-pnenyi-ammo m-~l=uyvriz C(=O)-N- carboxylic acid morpholino)-O-JUz-Nriz ri ~riz aril-~riz-r-pnenyi-ammo m-~l=uJwriz C(=O)-N- carboxylic acid morpholino)-O-JUZ-mriz ri ~:riz-~;ril-~;riz-~,ri3 pnenyi-ammom-~;l=vlivriz C(=O)-N- carboxylic acid morpholino)-o-~uz-lvtiz r~ ~;riz-pail-~;rizSri;-u-pnenyi-ammom-L(=u)Nriz C(=O)-N- carboxylic acid . moipholino)-o-~uz-mriz r~ ~riz-Sri(-~ri2~sn-u-pnenyi-ammom-~l=u~wriz C(=O)-N- carboxylic acid morpholino)-o-SUz-NHz H C;Hz-C;H(-CHz-Methyl phenoxy-aceticm-(:(=NH)NHz C(=O)-N- acid ester morpholino)-o-SOz-NHz H CHz-CH(-CHz-Methyl Cl-phenoxyacehcm-(:(=NH)NHz C(=O)-N- acid ester morpholino)-o-SOz-NHz H CHz-CH(-CHz-Methyl >~'-phenoxy-m-(:(=NH)NHz acetic C(=O)-N- acid ester moipholino)-O-JVz-Nriz H ~;Hz Lti(-~;tiz-Memyi Lti,-pnenoxy-m-~;l=mtyvriz C(=O)-N- acetic acid ester morpholino)-o-auz-ivHz t~ taizw;tyu;riz-tviemyi ~ri3-u-pnenoxy-m-~l=mryvriz C(=O)-N- acetic acid ester morpholino)-o-~uz-NHz m ;tiz-~;til-~;tizMetnyi ~sn-u-pnenoxym-~,l=mryvriz C(=O)-N- acetic acid ester morpholino)-o-SOz-NHz H CHz-CH(-CHz-Methyl Yhenoxyacehcm-C:(=U)NHz C(=O)-N- acid ester morpholino)-o-SUZ NHz H C;Hz-C;H(-(:Hz-Methyl (:l-phenoxyacehcm-(:(=U)NHz C(=O)-N- acid ester morpholino)-o-SOz-NHz H CHI CH(-(:Hz-Methyl r'-phenoxyacehcm-(:(=U)NHz C(=O)-N- acid ester morpholino)-o-~uz-Nriz r~ ~riz-aril-~riz-enemy ~ri3-pnenoxy-m-~l=vyvriz C(=O)-N- acetic acid ester morpholino)-o-~uz-Nriz ti ~riz pry-~riz-enemy ~ri3-u-pnenoxym-~l=u~wriz C(=O)-N- acetic acid ester morpholino)-o-~uz-wHz H ~riz Sri(-~riz-memyi rsn-u-pnenoxym-~l=u~wriz C(-0)-N- acetic acid ester morpholino)-o-SUz-NHz H C;Hz-(:H(-(:Hz-Yhenoxyacehc m-(:(=NH)NHz acid C(=O)-N-morpholino)-o- z- z z- r -p enoxy-acetic m- )NHz aci w.~ v~ m-morpholino)-o-SUz-NHz H CHz CH(-CHz-F-phenoxy- aceticm-C(=NH)NHz acid C(=O)-N-morpholino)-o-SUz-NHz H CHz-CH(-CHz-CH3-phenoxy-aceticm-C(=NH)NHz acid C(=O)-N-morpholino)-o-SUz-NHz H CHz-CH(-CHz-CH3-U-phenoxy-aceticm-C(=NH)NHz C(=O)-N- acid morpholino)-o-SUz-NHz H CHz-CH(-CHz-tan-U-phenoxy m-C(=NH)NHz acetic acid C(=O)-N-morpholino)-o-SUz-NHz H CHz-CH(-CHz-Yhenoxyacehc m-C(=U)NHz acid C(=O)-N-morpholino)-o-SUz-NHz H CHz-CH(-CHz-Cl-phenoxyacehc m-C(=U)NHz acid C(=O)-N-morpholino)-o-SOz-NHz H CHz-CH(-CHz-F-phenoxyacehc m-C;(=U)NHz acid C(=O)-N-moipholino)-o-SOz-NHz H CHz-CH(-CHz-CH3-phenoxy-aceticm-C(=U)NHz acid C(=O)-N-morpholino)-o-SOz-NHz H CHz-CH(-CHz-CH3-U-phenoxy m-(:(=U)NHz acetic C(=O)-N- acid morpholino)-o-SU2 NHz H CHz-CH(-CHz-Bn-U-phenoxy m-(:(=U)NHz acetic acid C(=O)-N-morpholino)-O-JVZ Nriz ti uriz-aril-uriz-rnenoxyemanoi m-~l=wrywriz C(=O)-N-morpholino)-o-~uz wtiz r~ ~riz-aril-~rizm-pnenoxy-emanoim-~l=wrywriz C(=O)-N-morpholino)-o-~uz-wtiz r~ ~riz-~ry-uriz-r-pnenoxy- emanoim-~l=wrywriz C(=O)-N-morpholino)-o-JUz-Nriz ti ~riz-~rtl-~:rlz-~;r13-pnenoxy-emanolm-~;l=wrywriz C(=O)-N-morpholino)-o-~uz-wtiz ti ~tiZ aril-~:riz-t_;ti3-u-pnenoxy-emanoim-t,l=mryvriz C(=O)-N-morpholino)-O-JVz-Nriz rm alz-Lrll-Lriz-~sn-u-pnenoxy m-~l=mryvriz emanoi C(=O)-N-motpholino)-o-~uz-Nriz ri ~riz-~nl-~nz-rnenoxyemanoi m-~l=v~wriz C(=O)-N-morpholino)-o-~uz-wtiz r~ ~riZ aril-uriz-~.;i-pnenoxyemanoim-~l=uJwriz C(=O)-N-morpholino)-o-~uz-Nriz r~ ~nz-uril-unz-r-pnenoxy-emanoim-c:l=ulwriz C(=O)-N-morpholino)-O-JUZ-ivriz ri ~riz-aril-tJriz-~ri3-pnenoxy-emanoim-~l=u~wriz C(=O)-N-morpholino)-o- z- z H CHZ- z- 3- -p ienoxy= m- )NHZ
vlll-trll ethano l.~' V
lJll V 1 1 C(=O)-N-morpholino)-O-JVz-iVriz ten -nz-~ril-Lnz-~n-u-pnenoxy- m-Ll=V~rrtiz emanoi C(=O)-N-morpholino)-O-JVz-Nriz ri ~riz-Sri(-~riz-Merry pnenoxy-eyum-ul=rrryNriz C(=O)-N- ether morpholino)-O-JUz-Nriz ri ~riz-Sri(-~riz-enemy m-pnenoxyemyim-ul=rrriJr~riz C(=O)-N- ether morpholino)-O-JVz-rrriz ri ~riz-aril-~riz-Memyi r-pnenoxy-emyim-~:l=mtiJr~riz C(=O)-N- ether morpholino)-O-JVz-rrriz ri ~riz-aril-~riz-nnetnyi ~ti3-pnenoxy-m-~;l=Ntyr~tiz C(=O)-N- ethyl ether morpholino)-O-JVz-Nriz ri tltiz-~;ri(-~:riz-Memym;ti3-v-pnenoxy-m-~:l=rVryvriz C(=O)-N- ethyl ether morpholino)-o-~uz-~tiz ti ~riz-~:ril-~;tizenemy nn-v-pnenoxym-~:l=rrryrVriz C(=O)-N- ethyl ether morpholino)-o-~uz-lvtiz ti LrirLril-Lnz-Memyl rnenoxyetnyim-~:l=~lrVriz C(=O)-N- ether moipholino)-~
o- z- z z- r enoxye y m- z a y -p C(=O)-N- ether morpholino)-o-~uz Ntiz ti ~riz uri(-~riz-Memyi r-pnenoxyemyim-~l=v~r~riz C(=O)-N- ether morpholino)-O-JVz-lVtlz h l:rlz-fall-laiz-Memym;ti3- m-~;l=V)r~riz C(=O)-N- phenoxyethyl ether morpholino)-o-~uz-Ntiz ti ~riz-aril-uriz-Memyi Sri; V- m-~l=V~r~riz C(=O)-N- phenoxyethyl ether morpholino)-o-~uz-Nriz ti ~riz-~:ril-uriz-nnemyi tsn-v- m-~l=V~rVriz C(=O)-N- phenoxyethyl ether morpholino)-O-JVz Ntiz t~ ~riz-~;ty-~;rtzpnenyi m-~:l=r~rywriz CHZ S(O)z-CH3 o-~uz-Nriz t-~ Ltiz-~:ril-trtiz-m-pnenyi m-t.l=rVrilrVriz CHz-S(O)z-CH3 O-JVz-Nriz ri ~ri2 ~;tt(-~tiz_-p eny m- z CHz-S(O)z-CH3 O-JUZ-Nriz z- z- 3-p eny . m- z CHz-S(O)z-CH3 o-~uz Nriz ri ~riz-aril-~riz~ri~-u-pnenyi m-~l=rrti~r~riz CHz-S(O)z-CH3 o-~uz ~riz r~ ~riz-aril-~rizrsn-u-pnenyi m-~l=r~ryrVriz CHz-S(O)z-CH3 O-JVz-t~riz ri ~riz-aril-~riz-p eny m- z CHz-S(O)z-CH3 O-~uz-Nriz ri ~riz-girl(-~riz-p eny m- z CHz-S(O)z-CH3 o-~uz Ntiz t~ ~tiz-Ltil-trtizr-pnenyi m-t_;l=vyvriz CHz-S(O)z-CH3 O-JVz rrriz n ~tiz-~;nl-~riz-Sri,-pnenyi m-~l=V~r~riz CHz-S(O)z-CH3 o- z- z I~ z- z- 3 -p ienyI m- z CHz-S(O)z-CH3 O-JUz-Nriz z- z- n- -p eny m- z CHz-S(O)z O-JUZ-Ntiz ri ~riz-~;ri(-t,riz-amime p-~;~=Nry~riz CHi S(O)z-CH3 o-~uZ Ntiz ~riz-~;ry-~;tiz~;i-amime p- z CHz-S(O)z-CH3 O-JUz Ntiz ti lalz-Lr1(-lalz-r-amlme p- z CHz-S(O)z-CH3 o-auz-Nriz ri ~riz-pry-~riz~:ri3-amime p- z CHz S(O)z-CH3 o-auz-Nriz tm :riz-qty-~tiz-~ai3 u-amnne p- z CHz-S(O)z-CH3 o-~uz Ntiz m :riz-~:ry-taiz-tsn-u-amime p-~~=NryNriz CHz-S(O)z-CH3 O-JUy-Ntiz n lalz l.rl(-t_;tlz-Hnllme p-l.~=u)Ntl2 CHz-S(O)z-CH3 o-~u2 Ntiz ri ~riz-pry-~riz-m-amime p-~~=u~Nriz CHz S(O)z-CH3 o-JUz NHz n t;rtz-Lti(-Lrlz-r-anllme p- z CHz-S(O)z-CH3 o-JUz-Nriz n c:riz-c:ri(-unz-~;rt,-amlme p- z CHz-S(O)z-CH3 o-~u2-Ntiz n ~tiz-~;ty-~;tiz-~;ri3-u-amime p- z CHz-S(O)z-CH3 o-~u2-Ntiz n z z- n- -am me p- z CHz-S(O)z-CH3 O-JUz-Ntlz ti caiz-~:rt~-caiz-rnenyi-ammo-carooxyncm-~~=mryNriz CHz-S(O)z-CH3acid o-JUZ-Ntiz ti l:rlz-Cat(-~:rlz-eny -ammo m- z CHz-S(O)z-CH3carboxylic acid O-SUz-NHz H ~;tiz-Lty-Ltiz-r-pnenyi-ammo m-~;~=NryNriz CHz-S(O)z-CH3carboxylic acid o-SU2 Ntiz H Caiz-c:11(-~;ttz-~;ri3-prienyl-ammom- z CHz-S(O)z carboxylic acid o- r z z- r s- -p eny ammo m- z CHZ S(O)z carboxylic acid o- z- z z- z- n- -p eny ammo m-~:~=NryNriz CHZ S(O)z carboxylic acid o-JUz NHz ri ~-riz-~-ril-~-riYrnenyt-ammo carooxyncm-~~=u~Nriz CHz-S(O)z-CH3acid o-~u2 NHz t1 lalz-l;tl(-1x12-ca-pnenyi-ammo m-~~=u)Nriz CHz-S(O)z-CH3carboxylic acid o-~uz NHz H Ltiz-Lti(-Ltiz-r-pnenyi-ammo m-~~=u~Nriz CHz-S(O)z-CH3carboxylic acid o-~u2-Ntiz m ai2 ~:ry-~;riz-~:ri3-pnenyi-ammom-~,~=uyvriz CHz-S(O)z carboxylic acid O-JUz-Nriz H l:rlz-l:ri~-1.;ri2-~ri3 u-pnenyi-ammom-~~=u~Nriz CHz-S(O)z-CH3carboxylic acid o-5uz NHz ri Lrlz-uty-uttz-tsn-u-pnenyi-ammom-~~=u~Nriz CHz-S(O)z carboxylic acid CH, o-SOz-NHz H C;Hz-(:H(-(:Hz-Methyl phenoxy-aceticm-C;(=NH)NHz CHZ S(O)Z acid ester o-SOz NHz H z- z- a y -p enoxyacehcm- z CHZ S(O)z-CHjacid ester o-S~-Nl~ H CHz CH(-CHz-Methyl l.'-phenoxy-m-(:(=NH)NHz acetic CHz-S(O)z-CH3acid ester O-JUz-NHz ti l;tlz lai(-laiz-a Y s-p epoxy- m- z CHz-S(O)z-CH3acetic acid ester o-~uz-Ntiz m aiz-gay-~tiz-a Y 3 -p epoxy- m- z CHz-S(O)z-CH,acetic acid ester o- z- z z- z- a iy n- -p epoxym- z CHz-S(O)z-CHjacetic acid ester o-SUz-NHz H (:Hz-C;H(-(:Hz-Methyl Yhenoxyaceticm-(:(=U)NHz CHz-S(O)z-CHjacid ester o-SUz-NHz H C:Hz-C;H(-(:Hz-Methyl (:1-phenoxyacehcm-(:(=U)NHz CHz-S(O)z-CH3acid ester O-JVZ-ivriz ri t,riz-~;ri(-~riz-memyi r-pnenoxyacencm-~~=u~ivtiz CHz-S(O)z-CH3acid ester O-JUz-wriz ri ~riz-Sri(-~riz-Memyi ~ri3-pnenoxy-m-~~=u~wriz CHz-S(O)z-CH3acetic acid ester O-JUz-Nriz z- z- a y 3- -p epoxy m- z CHZ S(O)z-CH3acetic acid ester o- r z z- z- a y n- -p epoxy m- z CHz-S(O)Z acetic acid ester o-SUz-NHz H C:Hz-C:H(-C;Hz-Yhenoxyacehc m-C;(=NH)NHz acid CHz-S(O)z-CH3 o-SOz-NHz H z- z- -p epoxy-acetic m- z aci CHz-S(0)z-CH3 o-SOz-NHz H z- z- -p epoxy- aceticm- z aci CHz-S(O)z-CH3, o-SOz-NHz H C:Hz-C;H(-(:Hz-(:H3-phenoxy-aceticm- z acid CHZ S(O)Z
o-SOz-NHz H C;Hz-(:H(-CHz-C;H3-U-phenoxy-aceticm-(:(=NH)NHz CHz-S(O)z-CH,acid o-SOz-NHz H C:Hz-(:H(-(:Hz13n-U-phenoxy m-(:(=NH)NHz acetic acid CHz-S(O)z-CH3 o-SOz-NHz H (:Hz (:H(-C;Hz-Yhenoxyacehc m-(:(=U)NHz acid CHz-S(O)z o-SOz-NHz H (:Hz C;H(-C;Hz-C;1-phenoxyacehcm-(:(=U)NHz acid CHz-S(O)z-CH3 o-SOz-NHz H z z- -p enoxyacehc m- z aci CHz-S(O)Z
o-SOz-NHz H r z- 3-p epoxy-aceticm- z aci CHz-S(O)z-CH3 o-SOz-NHz H r z- s- -p epoxy aceticm- z CHz-S(O)z-CH3acid o-SOz-NHz H CHz-C;H(-(:Hz-Bn-U-phenoxy m-(:(=U)NHz acetic acid CHz-S(O)z-CH3 o-JUz-lVtiz z- z- enoxye o m- z CHz-S(O)z-CH3 O-JUz-lVriz z- z- -p epoxy-a ano m- z CHz-S(O)z-CH3, O-~uz-Nriz t-~ Ltizwayuay-r-pnenoxy- etnanoim-~~=mryvriz CHz-S(O)z-CHj O-~Vz-lVriz t-~ Ltizwayuaiz-~-ri3-pnenoxy-emanoim- z CHz-S(O)z-CH, o-~uz-Ntiz tt Ltiz-~ti(-~tiz-~ri3-u-pnenoxy-emanoim-~~=wrywriz CHz-S(O)z-CH3 o-~uz-lrtiz r~ ~ni ~nl-~ri~rsn-u-pnenoxy m-~~=wtiyvriz emanoi CHz-S(O)Z
CHj O-~Vz-NHz ti Ltiz-cay-~riz-rnenoxyemanoi m-~~=u~wriz CHz-S(O)z-CH3 O-JVz-Ntlz ri l;riz-l:rl(-l:rlz-~;i-pnenoxyemanoim-~~=vyvriz CHz-S(O)z-CH3 O-JVz-Nriz ri ~riz-qty-~riz-r-pnenoxy-emanoim-~~=uyvriz CHz-S(O)z-CH3 O-JVZ-Ntlz h lalz-l:rl(-1;t12-~ri3-pnenoxy-emanoim-~~=u~rrriz CHz-S(O)z-CH3 O-JUz-wtiz r~ ~tiz-~;ty-~riz-~:ri3-u-pnenoxy-m-~;~=uyvriz emanoi CHz-S(O)z-CH3 o- z- z z- z- n- -p epoxy- m- z a ano CHz-S(O)z-CH3 o-- z H CHZ- z- a y phenoxy-a m_ w aa wad-w,.m y mr~ ma~mu m am au i m CHz-S(O)z-CH3ether o-SUz Hz H C;Hz-(:H(-C:Hz-Methyl (:1-phenoxyethylm-(:(=NH)NHz N
CHz-S(O)i ether o-~uz-Nriz ~riz-~ty-~tiz-iviemyi r-pnenoxy-emyim-Ll=~ti)Nriz CHz-S(O)z-CH,ether o-~u2 riz m ;riz-aril-~;tiz-ivietnyi ~ri3-pnenoxy-m-~:l=~ryvriz N
CHz-S(O)z-CH,ethyl ether O-JUz-lVtiz r1 l:riy-l:ril-1x12-ivietnyi ~ri3-u-pnenoxy-m-~l=Nrywtiz CHz S(O)z-CH3ethyl ether o-~u2 riz n ~riz-aril-~riz-ivietnyi rsn-v-pnenoxym-~l=rVryr~riz N
CHz-S(O)z-CH3ethyl ether O-JVZ-wtiz ri ~;riz ~:ril-~:riz-iviemyi rnenoxyemyim-~;l=u~r~riz CHz-S(O)Z ether o-~u2 tiz ti ~riz aril-~riz-ivietnyi m-pnenoxyemyim-~l=u~~riz lV
CHz-S(O)z-CH3ether O-JVz-Nriz ri ~riz ~;ril-~:riz-iviemyi r-pnenoxyewyim-~:l=u~wriz CHz-S(O)z-CH3ether o-~UZ-Ntiz 2- z- a y ~- m- z CHz-S(O)z-CH3phenoxyethyl ether o-~uz-ivtiz tm aiz pail-~;riz-iviemyi ~ti3-u- m-~;l=u~r~riz CHz-S(O)2 phenoxyethyl CH3 ether o-z- z r r a Y n- m- z CHz-S(O)z-CHjphenoxyethyl ether o-5Vz-Nriz rm :riz-pail-~aiz-pnenyi m-~l=mriyvriz hexane)-o-5Vz-Nriz ti z- z- -p eny m- z hexane)-O-5Vz-NHZ H laiz-fail-l;riz__p eny m-hexane)-O-JVz-NHz ti l:ti2l;ril-1:ri2-lal3-phenyl ~ m-hexane)-O-JUz-Nriz ri ~ri2 aril-~riz-~;ti3-u-pnenyi m- z hexane)-o-JUz-Nr12 tl CaizW ailWriri-v-phenyl m- z air hexane)-o-~u2 tiz tm ;tiz-~;til-~;riz-pnenyi ~ m- z iv hexane)-O-JVz HZ ri l:riz-fail-l;riz-l:l-phenyl m-N
hexane)-O-JVZ-NHZ H l:riz fall-C;riz--p eriy m-hexane)-O-JUz-NHz H Calz-C:ril-(:riq-3-p eriy m- z hexane)-O-JUZ-Nriz ti ~ z- ,- -p eny m- z hexane)-O-SVZ-Nriz H caiz t,til-caiz-tsn-u-pnenyi m-~l=v~~riz hexane)-o-~VZ HZ tl z- z- n1 me p- z N
hexane)-O-JUZ-Ntiz ti laiz-fall-l:rlz-l:l-anllme p-l:l=lVri)lVrlz hexane)-o-~Uz-Nriz W aiz-fail-~:riz-r-amtme ' p- z hexane)-O-JUz t12 ri lalz-l:ril-l;tiz-1x13-arillllle p-l;l=1Vri)lVrtz N
hexane)-O-JUz-iVtlz ti laiz fail-(_atz-(a13-u-anllme p-tJl=irrl)tvrl2 hexane)-o-~uz-lutiz r1 ~riz-aril-~riz-rsn-v-amime p- z hexane)-O-JVz-Ntiz ti l;tiz-C:ril-laiz-Alllllrie p-l.l=V)lVri2 hexane)-o- z- z z- z- -am me p- z ,.~ ~~.,~~
hexane)-O-JUZ-Nriz ri ~;riz-aril-t,riz-r-anume p-~l=u~wriz hexane)-O-JVz-IVHZ ri l.tlz-l.tll-l,tlz-~:H3-amune p-~;l=uyvriz hexane)-o-~uz-NHz m aiz-~;ril-t,riz-~:H3-u-amime p-t,l=uyvriz hexane)-o-~uz-NHZ rm aiz-~:ril-t,riz-tsn-u-amime p-~l=a yvriz hexane)-o-auz NHz ri ~HZ-~ry-~rtz-rnenyi-ammo-carnoxyncm-~l=NH~Nriz hexane)- acid o-JVz lVHZ H l;rlz-l:Hl-l;HZ-l;l-Yneriyl-ammom-l:l=1Vri)lVrlz hexane)- carboxylic acid O-JVz NHZ H l:HZ-l:Hl-l:HZ-r-pnenyl-ammo m-l.:l=lVr1)lVrlz hexane)- carboxylic acid O-JUz-NHz ri ~riz-aril-~riz-~Hj-pnenyi-ammo m-~l=NHJNriz hexane)- carboxylic acid o-au2 NHz H ~HZ-~Hl-~HZ-~H3-u-pnenyi m-~l=NriJwriz ammo hexane)- carboxylic acid o-~uz NHz H ~riz-~Hl-MHz-~sn-u-pnenyi m-~l=NryNriz ammo hexane)- carboxylic acid o-~uz-NHZ H ~:rirt-ty-~HZ-rnenyi-ammo carooxyncm- z hexane)- acid O-JVz-NHz ri ~riz-aril-~riz-~a-pnenyi-ammo m- z hexane)- carboxylic acid o-~uz NHz H LHz-~:Hl-~:HZ_-p eny -ammo m- z hexane)- carboxylic acid o-~uz NHz H Ltiz-tJHI-~:HZ-j-p eny -ammo m- z hexane)- carboxylic acid O-JVz-NHz H C:Hz-l:Hl-l;Hz1;H3-V-prieriyl-ammom-l:l=V)lVrlz hexane)- carboxylic acid o-JVz-NHz H C:HZ C;HI-(:Hz-t5ri-V-prieriyl-alrilll0m- z hexane)- carboxylic acid o- 02-NHz H CHz-CH(-CHz-Methyl phenoxy-aceticm- z hexane)- acid ester o-SOz-NHz H CHz CH(-CHz-Methyl Cl-phenoxyacehcm-(:(=NH)NHz hexane)- acid ester z- z z- z- a y -p epoxy- m- z aceric hexane)- acid ester o-~u2 NHz H ~HZ-~Hl-~HZ-nnemyi ~H3-pnenoxy-m- z hexane)- acetic acid ester O-JUz-NHZ ri ~;riz-aril-~riz-nnemym,H3 u-pnenoxy-m-~l=ivHyvriz hexane)- acetic acid ester O-JVz-Nriz H LHz ~Hl-~HZ-enemy tsn-u-pnenoxym-~l=NH~Nriz hexane)- acetic acid ester o-SUz-NHz H CHz-CH(-CHz-Methyl Yhenoxyacehcm- z hexane)- acid ester o-SOz-NHz H CHz-CH(-CHz-Methyl C1-phenoxyacehcm- z hexane)- acid ester o-SOz-NHz z- z- a y -p enoxyacericm- z hexane)- acid ester o- z- z z- z- a y 3-p epoxy- m- z hexane)- acetic acid ester o-~uz-NHz H MHz ~Hl-~ry-enemy ~ri3-u-pnenoxym-~l=uyvriz hexane)- acetic acid ester o-~uz ut-iz z- z- a y n- -p epoxy m- z hexane)- acetic acid ester o-SUz-NHz H CHZ CH(-CHz-enoxyacehc aci m- z hexane)-o-SOz-NHz H CHz-CH(-CHz--p epoxy-acetic m- z aci hexane)-o- z- z r z- -p enoxy- aceticm- z .~ aci hexane)-o-5Uz-NHz H C:Hz-(:H(-(:Hz-(:Hj-phenoxy-aceticm-(:(=NH)NHz acid hexane)-o-SUz-NHz H C;Hz-C:H(-C;Hz-(:H3-U-phenoxy-aceticm-(:(=NH)NHz hexane)- acid o-5Uz-NHz H C:Hz-(:H(-C;Hz-tan-U-phenoxy m-(:(=NH)NHz acetic acid hexane)-o-SUz-NHz z- r enoxyacehc aci m- z hexane)-o-5Uz-NHz r r -p enoxyacehc m- z aci hexane)-o-SUz-NHz H C;Hz-C:H(-(:Hz-r'-phenoxyacehc m-(:(=U)NHz acid hexane)-o-SOz-NHz H z- r 3-p enoxy-aceticm- z aci hexane)-o-SUz-NHz H C;Hz-(:H(-(:HZ(ai3-U-phenoxy m- z acetic hexane)- acid o-SUz-NHz H (:Hz-(:H(-C;Hz-tan-U-phenoxy m-C:(=U)NHz acetic acid hexane)-o-~uz-mtiz r~ l:riz-aril-laizenoxye ano m- z hexane)-o-~urmtiz ti ~nz-~-ril-1-nz-~-i-pnenoxy-emanoim-l.l=mryvriz hexane)-o-~uz-mtiz t~ ~tiz-uril-uriz-r-pnenoxy- emanoim-l:l=wryvriz hexane)-O-JUz-mHz ri laiz-fail-t~rizl:ri3-pnenoxy-etnanoim-l:l=mryvriz hexane)- -o-~uz-ivriz t~ 2 r 3- -p enoxy-a m- z ano hexane)-o- z- z r z- n- -p enoxy a m- z ano hexane)-o-~Vz-Ntiz tt l:riz t_;ryu:riz-rnenoxyemanoi m-1.1=~yvriz hexane)-o-JUz-NHz z- z- -p enoxye ano m- z hexane)-o- z- , z- r -p enoxy-a ano m- z hexane)-o-5uz-NHz H laiz-fail-Lrizurl3-pnenoxy-emanoim-~l=u~wriz hexane)-o-~uzuvtiz ti Lnz-~-ril-1-nz-3- -p enoxy- m- z a ano hexane)-O-JUZ-NHz ti 1x12-fail-1;t12-ri- -p enOXy- m-a ano hexane)-o-5uz NHz tt Ltiz tail-l:riz-enemy pnenoxy-emyim-l:l=mryvriz hexane)- ether O-~Vz-ivtiz ri l:riz-tail-laiz-nnemyi la-pnenoxyemyim-l:l=mryvriz hexane)- ether o-~uz-lVtlz tl 1,t12-l.rll-1.r12-nnerxiyi r-pnenoxy-emyim- z hexane)- ether o-~uz-ivttz tm _aiz-tail-laiznnemyi l:ri3-pnenoxy-m-l:l=mriyvriz hexane)- ethyl ether o-~uz-ivtiz ti ~tiz-tail-laiz-enemy ~r13-u-pnenoxy-m-l:l=mryvriz hexane)- ethyl ether o-~uz-Ntiz ti l:riz-lay-uriz-Memyi nn-u-pnenoxym-l:l=wrywriz hexane)- ethyl ether O-JUz ivtiz t~ lai2 ~-til-l:riz-enemy rnenoxyetnyim-l:l=uyvriz hexane)- ether o- z- z z- z- a y -p enoxye m- z y hexane)- ether o-~uz-ivtiz tm ;tiz-l:ry-l:rtz-nnemyi r-pnenoxyemyim-l:l=a yvriz hexane)- ether o- ~ H z- z- a m- z U Y
s-hexane)- phenoxyethyl ether o-~uz-Nrlz ti t:rlz-fall-lalz- Mettlyl t~ri3-u-m-l:l=u)Nrlz hexane)- phenoxyethyl ether O-JUZ-Nrlz ri ~riz-aril-~tiz_ ivlemyi tsn_u- m-~l=u~Ntiz hexane)- phenoxyethyl ether O-JUZ-Nrlz ri ~.riz-~:ril-t.riz-pnenyl m-~l=NryNriz (HO-phenyl))-o-~uz-Nriz rl ~riz-aril-~riz-m-pnenyi m-ul=Nn~Nriz (HO-phenyl))-o_JUZ-Nriz ri ~;riz-l:rll_l:rlz_r-pnenyi m-~l=Nti~Nnz (HO-phenyl))-o-~uz-Ntiz r r a-P m- z eny (HO-phenyl))-O_luz-Nri2 H 1x12-fall-l.;riz_l:rig_u-pnenyl m-l:l=Nri)Nri2 (HO-phenyl))-O_JUz_Nri2 z- z- n- m_ z -p eny (HO-phenyl))-O-JU2_Nriz Y z- pnenyl m- z (HO-phenyl))-o-~u2 rlz z- Z -p m- z N eny (HO-phenyl))-o-~uz-Ntiz ti uriz-aril-c:rlz-r-pnenyl m-~l=u~Nriz (HO-phenyl))-O-JUz-Nriz ri t~riz-t,rll_~riz-~:ri,_pnenyi m-l.l=u~lrriz (HO-phenyl))-O-JUz-Nriz ri ~riz-aril-~riz-3_ m- z _p eny (HO-phenyl))-O_JUZ_Nri2 tl uriz-aril-~riz-~n-u-pnenyi m-~l=u~Nriz (HO-phenyl))-O-JUz-Ntiz ti lai2 Call-1x12-Amillle p-l.;l=Ntl)1Vr12 (HO-phenyl))-o-5u2 rlz n tai2 fall-Ltlz-t_;1-aniline p- z N
(HO-phenyl))-o-~ui tiz rl ~-rir~-ril-~riz-r-anume p_l:l=lVr1)lVrlz N
(HO-phenyl))-O-~uz-Nriz ti ~riz-aril-~riz~r13-aniline p-~l=NryNriz (HO-phenyl))-o-~uz tlz tl lalz-~til-~tiz-~r13-u-amlme p- z N
(HO-phenyl))-O-JVz-NHz ti Cain-l~rtl-l:riz-II_ p--anlllle (HO-phenyl))-o-aVz-Ntl2 ti Cain-l:rll-lalz-m p-me (HO-phenyl))-O-JVz-Ntl2 ti C:rlz l:rll-l:rlz_-am p- z me (HO-phenyl))-o-JVz tiz tl z- z- -am p- z N me (HO-phenyl))-o-~Uz-Ntiz tl 1a12-l:rll-~;rtz-~;r13-anllme p-~:l=u)Nrlz (HO-phenyl))-o-5u2 tlz tl Ltlz aril-~tiz-t_;r13-u-aniline p-~l=u~Nriz N
(HO-phenyl))-O-~uz-Nriz ti taiz-~:ril-~tiz-tsn-u-anllme p-~:l=u~Nriz (HO-phenyl))-O_lUz_Ntly ti l.riy_f.rll_1,r12-Ynenyl-amlri0-CarDOXyliC
m-l:l=Nrl)Nriz (HO-phenyl))-acid o-JUz_Ntl2 11 l:riz-l;ril-1:ri2-l:l-Yrieriyi-ammo m-l:l=Nrl)Nrl2 (HO-phenyl))-carboxylic acid o-~uz-Ntlz m :rlz_f,rll-l:rlz-r-pnenyi-amino m-~;l=l~rl~i~rlz (HO-phenyl))-carboxylic acid o-z- z z- z- s-P m- z eny -ammo (HO-phenyl))-carboxylic acid o_ - z H ~2_~ - z- 3_ _p eny~ ammo m- z (HO-phenyl))-carboxylic acid O-JUZ-Nriz ri ~riz-Sri(-~;HZ-tsn-u-pnenYi m-~~=r~HJ~ri2 ammo (HO-phenyl))-carboxylic acid o-~uz-Nriz n ~riz-~H~-~riz-rnenyi-ammo caruoxyncm-~~=u~NHz (HO-phenyl))-acid o-JUz-NHZ ri ~riz-~ri~-~:riz-m-pnenyi-ammo m-~~=uJNHz (HO-phenyl))-carboxylic acid o-JUZ-NHZ ri ~riz-Sri(-~:riz-r-pnenyi-ammo m-~~=u~wHz (HO-phenyl))-carboxylic acid O-JUZ-~riz ri ~:riz-t,ri(-~:riz-~ri3-pnenyi-ammom-~~=uJ~Hz (HO-phenyl))-carboxylic acid o-auz-~riz m :riz-~.ry-~;riz-~,ri3-u-pnenyi-ammom-~.~=u~r~riz (HO-phenyl))-carboxylic acid O-JUZ ~riz ri ~:ri2 Sri(-~;riz-tsn-u-pneny-ammom-~.~=u~mriz (HO-phenyl))-carboxylic acid o-SUz-NHz H CHZ CH(-CHz-Methyl phenoxy-aceticm-C(=NH)NHz (HO-phenyl))-acid ester o-SUz-NHz H CHz-CH(-CHz-a y -p enoxyacehcm- z (HO-phenyl))-acid ester o-SOz-NHz H CHz-CH(-CHz-a y -p enoxy- m- z acetic (HO-phenyl))-acid ester o-JVz-Nriz H z- z- a Y a-P enoxy- m- z (HO-phenyl))-acetic acid ester O-5U2-NHZ H l:H2l:H(-1;H2-MettlYllalg-u-pneriOXY-m-l;(=lVt1)lVriz (HO-phenyl))-acetic acid ester O-JUZ-Nriz H gay-~:Hl-c:Hz-Mertiyi tsn-u-pnenoxym- z (HO-phenyl))-acetic acid ester o-S~NHz H CHz-CH(-CHz-Methyl Yhenoxyacehcm-(HO-phenyl))-acid ester ~Oz-NHz H CHz-CH(-CHz-Methyl (:1-phenoxyacehcm- z (HO-phenyl))-acid ester o-SOz-NHz H CHZ CH(-CHz-Methyl r-phenoxyacehcm-C(=U)NHz (HO-phenyl))-acid ester O-JUZ-NH2 H ~;tiz-~;H(-~:HZ-metnym;ti3-pnenoxy-m- z (HO-phenyl))-acetic acid ester O-JUZ-NHz H ~tiz-~Hl-~HZ-Memy ~ri3-u-pnenoxym-~~=u~mriz (HO-phenyl))-acetic acid ester o-~uz-NHz H ~ry-~ry-~riz-enemy tsn-u-pnenoxym-~~=u~wri2 (HO-phenyl))-acetic acid ester o-SOz-NHz H CHZ CH(-CHz-Yhenoxyaceric m- z acid (HO-phenyl))-o-SOz-NHz H CHZ CH(-CHz--p enoxy-acetic m- z aci (HO-phenyl))-o- z-NHz H CHZ CH(-CHz-J~-phenoxy- aceticm- z acid (HO-phenyl))-o- z-~ r z- 3 p enoxy-aceticm- z aci (HO-phenyl))-z- z- 3- -p enoxy-aceticm- z o- z- z (HO-phenyl))-acid off- Oi-NHz H CHZ-CH(-CHz-Bn-U-phenoxY m-C;(=NH)NHz acetic acid (HO-phenyl))-0~0~ NHz H CHz-CH(-CHz-enoxyacehc aci m- z (HO-phenyl))-o-SOZ-NHz H CHz-CH(-CHz--p enoxyacehc m- z aci (HO-phenyl))-o-~ H CHz-CH(-CHz-F-phenoxyacehc m-C(=U)NHz acid (HO-phenyl))-o-SOi NHz H CHz-CH(-CHz-CH3-phenoxy-aceticm-C(=U)NHz acid (HO-phenyl))-o-SOz NHz H CHz-CH(-CHz-CH3-U-phenoxy m-C(=U)NHz acetic (HO-phenyl))-acid z- z H z- z- n- m- )NH2 -p enoXy acehc acid (HO-phenyl))-O-JUZ-Nriz ri l:riz-l:ril-laiz-rnenoxyemanoi m-l:l=wri)wriz (HO-phenyl))-O-JVz-NHz ~riz-~ry-LHzla-pnenoxy-emanoi m- z (HO-phenyl))-O-JVz-Nri2 ti laiz-l:ril-l:Hz-r-pnenoxy- m-l:l=Nri)Nriz etnanoi (HO-phenyl))-O-JVZ-Ntlz H l:Hz-l:ril-l:Hz-c:ri3-pnenoxy-emanoi m-l:l=Nri)Nriz (HO-phenyl))-O-JU2-Nriz H z- z- s- m- z -P
enoxy-a ano (HO-phenyl))-o-~uz-Ntiz ri l:riz-~ril-~-nz-~sn-u-pnenoxy m-l:l=wri)wriz emanoi (HO-phenyl))-O-JVz-Nriz ri ~-nz-~-nl-un2-rnenoxyemanoi m-l:l=u)wriz (HO-phenyl))-o-~uz-Nriz ri l:riz-lail-laiz-~i-pnenoxyeuianoi m-l:l=u)ivriz (HO-phenyl))-O-JUz-NHz H 1:ri2-l;Hl-l:tlz-r-pneriOXy-eLrianol m-l:l=V)Nri2 (HO-phenyl))-o-~u2 t12 ti 1x12-l;til-1x12-lai3-pnenoxy-emanoi m-1.1=u)ivriz N
(HO-phenyl))-O-JVZ-Nriy H l:rlz l.;ril-1:ri2-1;r13 m-V-pnenOXy-emari0l (HO-phenyl))-O-JUZ-NHZ H l:Hz-l:ril-l:Hz-t5ri-u-prienOXy- m-l:l=u)wriz emanoi (HO-phenyl))-o-JUZ-Nri2 H laiz-lail-laiz-a m- z Y
P
enoxy-a y (HO-phenyl))-ether O-JUz-NHZ . z- z- a m- z y -p enoxye y (HO-phenyl))-ether o-SOz Hz H CHz-CH(-C;Hz-Methyl m-CL(=NH)NHz N r'-phenoxy-ethyl (HO-phenyl))-ether o-5u2 Hz H l~tlz-loll-~;ti2lvlemy11:r13-pnenoxy- m- z N
(HO-phenyl))-ethyl ether o-~u2 Hz H l~tiz-fall-l;tlz-Mell1y11x13-v-prieriOXy- m-N
(HO-phenyl))-ethyl ether O-5Vz-NHz H C:HZ-l.Hl-l.Hz-lVleTllyl m-l.l=lVt1)1Vr12 tan-V-pnenOXy (HO-phenyl))-ethyl ether o-~u2 Hz H l:Hz-l:Hl-~riz-enemy m-l:l=u)mriz N rnenoxyemy (HO-phenyl))-ether O-JVz-NHZ H laiz-fail-l:riz-Merry m-l.l=v)ivriz 1:i-pnenoxyemyi (HO-phenyl))-ether O-~Uz-NHz H l:Hz-llril-l:riz-Meyu m-l.l=v)wriz r-pnenoxyemy (HO-phenyl))-ether o-~uz-NHz r~ laiz-fail-trti2nnemymai3_. m-l.l=u)wriz (HO-phenyl))- phenoxyethyl ether O-JUZ-NHz tl laiz-l.rll-1.r12-l VleLllyll.rlg-u-m-l:l=V)lVrlz (HO-phenyl))- phenoxyethyl ether o-JUz Hz ri l:riz-urll-l:riz- nnecnyi nn-v- m-l:l=v)wriz N
(HO-phenyl))-phenoxyethyl ether O-JVz-NHz H lal2-l:rll-l.;tlz-pnenyl m-l:l=Nrl)Nrlz (Cl-phenyl))-O-JU2 riz ri l:riz-l:ril-~riz-la-pnenyi m- z N
(Cl-phenyl))-o-z z z- z- -p m- z eny (Cl-phenyl))-o-~uz-Nriz ti l:riz-l:ril-~;tlzl:ri3-pnenyi m-l:l=wri)ivriz (Cl-phenyl))-O-JVZ-Ntl2 ti Lriz-Lril-Lriz-Lri3-V-Pnenyl m-l.l=LVri)lVriz (Cl-phenyl))-O-JUz-Nriz ti z z- n- m- z -p eny (Cl-phenyl))-= 127 -H ? z- p ieny m- z o- z- z (Cl-phenyl))-O-JUZ-Nriz ri ~,riz ~:ril-~:riz-~a-pnenyi m-~:l=u)Nriz (Cl-phenyl))-o-JVZ-Nriz ~riz-aril-~HZ-r-pnenyi m-~l=u)NHz (Cl-phenyl))-O-JVZ-Nriz ri ~;riz-~:ril-tlriz-~ri3-pnenyi m-~l=u)Nriz (Cl-phenyl))-o-~uz-NHZ H ~HZ-aril-~riz-~H3-u-pnenyi m- z (Cl-phenyl))-o-'uz-NHz rm ;tiz-~;Hl-~;Hztsn-u-pnenyi m-~:l=u)NHz (Cl-phenyl))-O-JUz-Nriz ri ~:riz-t,Hl-t.riz-Amime p- z (Cl-phenyl))-o-~uz-NHZ n ~riz-~Hl-~HZ-m-amime p- z (Cl-phenyl))-o-~uz-NHZ n ~riz-aril-~HZ-r-amime p- z (Cl-phenyl))-O-JUZ-NHz H l;Hz-l:Hl-1:H2-1:H3-anlllIle p- z (Cl-phenyl))-O-JUZ-NH2 ti l.rlz-lail-l:HZ-lalg-u-anllllle p-1.1=lVr1)lVriz (Cl-phenyl))-o-~uz-NHz H ~riz ~Hl-~rizrsn-u-amime p- z (Cl-phenyl))-O-JUZ NHz H 1;t12-loll-1x12-ATllllIle p-1.1=U)lVriz (Cl-phenyl))-o-~Vz-NHz H l:HZ-~:Hl-laiz~:1-anlllne p- z (Cl-phenyl))-o-~uz-NHz H LHZ LHl-MHz-r-amime p-~l=u)Nriz (Cl-phenyl))-O-JUy-NHz H l:riz l;Hl-lalz-3-am me p-(Cl-phenyl))-o-SUz-NHZ H z z- 3- -am me p- z (Cl-phenyl))-o-JUZ-NHz H l:Hz-l:Hl-t_;HZ-tSn-U-amlme p-Ll=u)lVriz (Cl-phenyl))-O-JUz-NHy H 2- z- eriy -amlll0-carm- z Oxy lc (Cl-phenyl))-acid o-1U2-NHz H l.Hz C.HI-l;Hz-l.l-Ynenyl-amln0m-l.;l=1VH)lVrlz (Cl-phenyl))-carboxylic acid o-5Uz-NHz H l:Hz C:HI-t;Hz-r-pnenyl-ammo m- z (Cl-phenyl))-carboxylic acid O-~Uz-NHz H LHz LHl-MHz-~H3-pnenyi-ammo m- z (Cl-phenyl))-carboxylic acid o-5Uz-NHz H ~;Hz LHl-t;HZ-~:H3-u-pnenyl m-~l=~H)~riz ammo (Cl-phenyl))-carboxylic acid O-JUZ-NHz H l.Hz C.,HI-l~Hz-tin-U-pnenyl m-l:l=lVr1)lVtlz ammo (Cl-phenyl))-carboxylic acid O-JUZ-NHz H 1;H2-(:Hl-l.;HZ-Yneriyl-amino m- z CarUOXyIIC
(Cl-phenyl))-acid O-~Vz-NHz H caiz ~Hl-LHZ-~1-pnenyi-ammo m-~l=v)Nriz (Cl-phenyl))-carboxylic acid o-~uz-NHz H ~HZ-~Hl-~rizr-pnenyi-ammo m-~l=~)mriz (Cl-phenyl))-carboxylic acid o-5uz NHz H MHz-~Hl-MHz-~H,-pnenyi-ammo m-~l=~)mriz (Cl-phenyl))-carboxylic acid o-5uz NHz H ~Hz-~Hl-c:Hz-uH3-u-pneny-ammom-~l=u)~r~z (Cl-phenyl))-carboxylic acid o-JUz-NHz H C.:Hz-l;Hl-1;H2-tin-u-pneriyl-ammom-l;l=v)i~riz (Cl-phenyl))-carboxylic acid o- z- a - H r z- a y p enoxy-acericm- z (Cl-phenyl))-acid ester z- z H z- r a y -phenoxyaceric W W i ~m .~ my~aa m- z (Cl-phenyl))-acid ester o-SUz NHz H CHz-CH(-CHz-Methyl F-phenoxy-m-C(=NH)NHz acetic (Cl-phenyl))-acid ester o-~uz-rVriz ri ~riz-pail-t.;tiz-Memyi t_;ti3-pnenoxy-m-~:l=mryNtiz (Cl-phenyl))-acetic acid ester O-JUZ-rVriz ri ~:riz t.ril-~:riz-Memyi ~ri3-u-pnenoxy-m-~l=rrryNriz (Cl-phenyl))-acetic acid ester o-~uz-rVriz ri ~riz-aril-~riz-Memyi ~n-u-pnenoxym-~l=NryNtiz (Cl-phenyl))-acetic acid ester o-SUz-NHz H CHz-CH(-CHz-Methyl Yhenoxyacehcm-(:(=U)NHz (Cl-phenyl))-acid ester o-SOz-NHz z- z- a Y -p enoxyaceticm- =U z (Cl-phenyl))-acid ester o-SOz NHz H CHz-CH(-CHz-a y -p enoxyacehcm- z (Cl-phenyl))-acid ester o-~uz-tvtiz z- z- a y ,-p enoxy- m- z (Cl-phenyl))-acetic acid ester o-SOz-NHz z- z- et Y a- -p epoxym- z (Cl-phenyl))-acetic acid ester O-JUz-Ntiz r~ ~riz-aril-~riz-Merry rsn-u-pnenoxym-~l=u~r~riz (Cl-phenyl))-acetic acid ester o-SOz-NHz H CHz-CH(-CHz-Phenoxyacehc m- z acid (Cl-phenyl))-o- Uz=NHZ H z z- -p epoxy-acetic m- z -- aci (Cl-phenyl))-o-SOz-NHz H CHz CH(-CHz--p epoxy- aceticm- z aci (Cl-phenyl))-o-SOz-NHz H CHz-CH(-CHz-CH3-phenoxy-aceticm- z acid (Cl-phenyl))-o-~Oz-N~ H CHz-CH(-CHzCH3-U-phenoxy-aceticm-C(=NH)NHz (Cl-phenyl))-acid o-SUz NHz H CHz-CH(-CHz-tin-U-phenoxy m-C(=NH)NHz acetic acid (Cl-phenyl))-o-SOz-NHz H CHz CH(-CHz-Yhenoxyacetlc m-(:(=U)NHz acid (Cl-phenyl))-o-SOz-NHz H CHz-CH(-CHz-Cl-phenoxyaceticm- z acid (Cl-phenyl))-o-SUz NHz H CHz-CH(-CHz-F-phenoxyacetlc m- z acid (Cl-phenyl))-o-SOz=NHz H CHz-CH(-CHz-3-p epoxy-aceticm- z aci (Cl-phenyl))-o-SOz-NHz H CHz CH(-CHz-3- -p epoxy aceticm- z (Cl-phenyl))-acid o-SOz-NHz H CHz CH(-CHz-n- -p epoxy aceticm- z aci (Cl-phenyl))-O-JUz-Nriz n ~:riz-Lnl-~riz-enoxye ano m- z (Cl-phenyl))-o-~uz-Nriz r~ ~tiz ~rtl-~riz--p epoxy-a ano m- z (Cl-phenyl))-o-~uz rvtiz rm aiz-~:ry-~;riz-r-pnenoxy- emanoim-~;l=mry~riz (Cl-phenyl))-O-JVZ-Nriz ti lalz-l:ril-(:riz-1:ri3-prieriOXy-elllanolm-l;l=iVrl)lVrlz (Cl-phenyl))-O-JVZ-lVriz ti laiz-l:rll-laiz-l:rlg-u-pnenOXy-eirian0lm-l;l=lVr1)1Vr12 (Cl-phenyl))-o-~uz Ntiz t~ Lnr~-ril-~riz-~sn-u-pnenoxy m-~;l=r~ryvriz emanoi (Cl-phenyl))-o-~uz-Ntiz r~ ~nz-~nl-~nz-rnenoxyemanoi m-~l=u~mriz (Cl-phenyl))-o-~uz-Ntiz ti ~tiz-aril-~-tiz~a-pnenoxyemanoim-t.l=a ~r~riz (Cl-phenyl))--o- H z- z ~-p m- z V V 11 enoxy-et 1 z ano z-(Cl-phenyl))-o-JUZ-Nriz ri ~:riz-~:ril-~;tiz-~H3-pnenoxy-emanoi m-~l=u)NHz (Cl-phenyl))-O-JUZ-Nriz ti l.tlz t,Hlw;ty-LH~-u-Pnenoxy- m-~;l=u)NHz emanoi (Cl-phenyl))-o-~uz-NHZ rm a~z-~:Hl-~:H2nn-u-pnenoxy- m-Ll=u)NHz etnanoi (Cl-phenyl))-o-~uz riz n ~riz-aril-urizenemy m-~l=NH)Nriz N pnenoxy-emy (Cl-phenyl))-ether o-auz HZ rm ;riz-~:ril-~:riz-Memyma-pnenoxyemyi m-~;l=~ri)wHz N
(Cl-phenyl))-ether o-JUz tiz rm ;rizw:Hlw;HZ-nnemyi m-~;l=r~ri)NHz N r-pnenoxy-emyi (Cl-phenyl))-ether O-JUz-NHZ ri ~riz-aril-~riz-nnetnym;H3-pnenoxy- m-~:l=NH)Nriz (Cl-phenyl))-ethyl ether o-JUz-NHZ ri ~;riz-aril-~riz-nnemyi m-~l=NH)NHz ~ri3-u-pnenoxy-(Cl-phenyl))-ethyl ether o-~uz-NHz z- z- a m- z y n--p enoxy (Cl-phenyl))-ethyl ether o-~uz-NHZ H ~riZ ~Hl-~HZ-Mewyi m-~l=u)r~Hz rnenoxyemyi (Cl-phenyl))-ether O-JUz-Ntiz ri uriz aril-~riz-Meyu m-~l=u)r~riz m-pnenoxyemy (Cl-phenyl))-ether o-~uz-NHz H ~:HZ-~:Hl-MHz-a m- z y -p enoxye y (Cl-phenyl))-ether o-JUZ-NHz z- z- a m- z y ~
(Cl-phenyl))- phenoxyethyl ether o-JUz-NHz H l;Hz l;til-(:Hz- nnetnym:ri,-u-m-~l=u)~riz (Cl-phenyl))- phenoxyethyl ether o-SOz-NHz H CHz-CH(-CHz- Methyllin-U- m- z (Cl-phenyl))-phenoxyethyl ether O-JUz-NHz t1 l;HZ-~:Hl-l:Hz-p m-eny , ~z)-O-JVz-NHZ H l:HZ-l:Hl-l:HZ-l:l-pnenyl m-l:l=lVri)lVriz ~z)_ O-JVy-NHZ t~ c:riz-aril-uHZ-r-pnenyi m-~:l=~ri)wriz ~z)_ o-'uz-NHZ H trHz ~Hl-~:riz-t.H3-pnenyi m- z ~z)-o-~uz-Ntiz n ~riz-pail-~:riy:ri3-u-pnenyi m- z ~z)-O-JUz-Nriz H ~riz-aril-~riz-rsn-u-pnenyi m-~l=Nri)rVriz ~z)-O-JVz HZ H ~riz-~:ril-~:HZ-pnenyi m-~;l=u)~riz N
~z)-O-JUz HZ H ~:riz-t,ril-~:riz--p m- z N eny NHz)-O-JUz-NHz H l:HZ-l:Hl-1;H2__p m_ eriy .
~z)_ o-z- z z- z- 3-P m- z enY
~2)-o-z- z z' z- 3 m- z -P
enY
~z)--- -o-z-~2 ~z ~(_CHz-Bn=O_phenyl m_C(=O)NHz ~z)-O-lUZ-lVHZ r1 z- z- m p- z me ~z)-O-JUZ-Nriz ri ~riz t.Hl-~riz-~;i-amime p-~l=NH)Nriz ~z)_ O-wz-NHZ ri ~ri2 ~Hl-~HZ-r-amime p-~l=Nri)Nriz ~z)-z- z- j-am me r,w iai m .~ ma ay.ra o- z- z p-~2)-o-50z-~Hz H CHz-CH - 3- -aniline p-C(=NH)NHz z-~z)-o-JU2 lVtiz r z- n- -am me p- z ~z)-o- z- z H CHz CH(=CHz-~I~e p-C(=O)NHz ~z)-O-JUz-wriz ri l:riz-~:ri(-l:riz-la-amime p-~.~=u)r~riz ~z)-o-~uz-tvtiz tt z- z- -am me p- z NHz)_ o- z- z CHz-CH(=CHz=-CH3-aniline p-C(=O)NHz ~z)-O-JVZ-Ntiz ti 1x12-lal(-lain-l.aig-V-anllme p-l:(=u)iVti2 ~2)-o-~uz-lvriz ti laiz-l:ry-l:riz-rsn-u-amime p-~;~=u)rVtiz ~z)-o-~uz-Ntiz ti lai2l:ry-laiz-rnenyi-ammo-carooxyncm-1.~=trti)rrtiz NHz)- acid o-JVZ-Ntlz n 1:ri2-l;ri(-1:ri2-l:l-Yneriyl-ammom-l,(=1Vri)1Vt12 NHz)- carboxylic acid o-~uz-Ntiz ti laiz-l:ry-l:riz-r-pnenyi-ammo m-1:~=rVri)Nriz NHz)- carboxylic acid O-JUz-NHZ t1 1:ri2-lal(-l:riz-1x13-pnenyl-ammom-l:(=lVr1)1Vt12 NHz)- carboxylic acid O-JVZ-NHZ H 1x12-lal(-lalzl:rig-u-prienyl m-1:~=lVt1)lVth ammo NHz)- carboxylic acid O-JUz-Nriz tt Lriz Lril-Lriz'~n-V-pneny ammo m- z NHz)- carboxylic acid O-~uz-Ntiz ti 2 z- eny -ammo car m- z oxy is NHz)- acid o-~Vz-Ntlz z- z -p eny -ammo m- z NHz)- carboxylic acid o- z- z z- z- -p eny -ammo - m=C( ~)NHz -..
NHz)- carboxylic acid o- z- z r r 3-p eny -amino -m-C
-~.aa a i NHz)- carboxylic acid o- r z z- z- 3- -p eny -aminom- ~ ~)~z - v Ul1 V a 1 NHz)- carboxylic acid o- z- z z- z- m-C(=O)NHz ~. ..
n- -p eny -amino NHz)- carboxylic acid o- z- z z- z a y p enoxy-aceticm- )NHz ~.. ~.. . .~ ,_.~ .,..
NHz)- acid ester o- z- z r z- a y -p enoxyacehcm-C(-NH)NHz NHz)- acid ester o-SUz-NHz H CHz CH(-CHz-a y -p enoxy- m- z acetic NHz)- acid ester O-JVz-rrtiz t~ l:riz l:ry-l:riz-Memyi l:ri3 pnenoxy-m-1:~=wri)rrriz NHz)- acetic acid ester o-~uz-Nriz r~ l:riz-l:ry-l;riz-rnemyi l:ri; m-1:~=rVri)rrriz u-pnenoxy-NHz)- acetic acid ester O-JUZ-1Vt12 t1 lalz-lal~-laiz-MeTtlyl tiri-V-pneriOXym-l:(=lVt1)lVriz NHz)- acetic acid ester o-SU2 NHz H CHz-CH(-CHz-Methyl Yhenoxyacehcm-C(=U)NHz NHz)- acid ester o-SUz-NHz H CHz-CH(-CHza y -p enoxyacehcm- z NHz)- acid ester o-SUZ NHz z- z- a y -p enoxyacehcm- z NHz)- acid ester o- z- z z- z- a Y 3-p enoxy- m-NHz)- acetic acid ester o- z- z z- r a 1y s- -p epoxym- z NHz)- acetic acid ester o- z- z z- z- a y n- -p epoxy m- z NHz)- acetic acid ester o-~ H CHz- z- enoxyacehc aci w.u~-w.ai ~~ mu~mu m- z NHz)-o-SUz-NHz H CHz-CH(-CHz-Cl-phenoxy-aceticm-C(=NH)NHz acid NHz)_ o-SUz-NHz H CHz-CH(-CHz-F-phenoxy- aceticm-C(=NH)NHz acid NHz)_ o_ _ z H ~_ ~3_~xy=acetic iiW~ NH)NHz acid ~z)-o- z' z z- r 3- -p epoxy-aceticm- z NHz)- acid o- z- z z- z- n- -p epoxy aceticm-C(=NH)NHz acid ~z)-o- z- z z- z- enoxyacehc aci w.~ vym m-o- r z -p enoxyacetic in-C(=O)NHz ,_,~. ,_,..~-,...acid i z- ,.. ~.
NHz)_ o-SOz-NHz H CHz-CH(-CHz->~-phenoxyacehc m- z acid ~z)-o-SOz-NHz H CHz-CH(-CHz-CH3-phenoxy-aceticm-(:(=U)NHz acid ~z)-o-SOz-NHz H CHz-CH(-CHz-CH3-U-phenoxy m- z acetic NHz)- acid o-SOz-NHz H CHz-CH(-CHz-Bn-U-phenoxy m-C(=U)NHz acetic acid ~z)-O-JUz NHz t1 lalz l;tll-1:112-YrieriOXyeitlan0lm-l;l=lVt1)lVriz NHz)_ O-~Vz-Nri2 t~ c:riz-pail-~aiz-t,i-pnenoxy-emanoim-~:l=mryvriz ~z)_ o-JUy-Nri2 t1 lalz-fall-lalz-r-prienOXy- eirianolm-NHz)_ O-JVy-Ntlz z- z- g-p eriOXy-a m-ari0 ~z)-o-~Vz-Ntiz tt uriz-~ril-~nz-~ri3-~-Pnenoxy-emanoim- z ~z)-O-JUy-lVri2 Y r n- -p epoxy a m- z ano ~2)-o- z- z z- z- enoxye ano m- z NHz)_ O-JVZ-NHZ ri ~ty;ry-~riz--p enoxye ano m- z ~z)-o-JVi NHz z Z- -p epoxy-a ano m-NHz)_ o-aVz-ivtiz z- z- 3-p epoxy-a ano m- z ~2)-o- z- z CH3-U-Phenoxy- m-C(=O)NHz .... ~..~~-~.,~.ethanol r z-~z)-o-~uz-mtiz ti trtiz t_;ril-~riz-isn-u-pnenoxy- m-~l=~yvriz emanoi ~2)-O-JU2-1Vt12 h l.:riz-l:ril-l:riy-Meuryi pnenoxy-emym-~l=wrywriz NHz)- ether o-auz-wriz m ;tizw;ty-~tiz-enemy m-pnenoxyemym-~l=ivryvriz NHz)- ether o-~uz-Nriz ri ~riz-~:ril-~riz-Memy r-pnenoxy-emym-~l=mryvriz NHz)- ether o-~uz-wtiz ri ~riz-aril-~riz-nnewyi ~ri3-pnenoxy-m-~l=wriyvriz NHz)- ethyl ether O-JU2-lVriz ti tatz-~;til-~tiz-enemy ~ri3-u-pnenoxy-m-~:l=mryvriz NHz)- ethyl ether ~
o-z- z r z- et m- z iy n--p enoxy NHz)- ethyl ether o- z- z- a w a as y .~ ma m z enoxye m- =O~ z z- y iva ua a a a ua m NHz)- ether o-z- Z- - CH2= z- a m-C(=O)NIT
. w a H .aa~- v.u y a~ m -phenoxyethyl ava ua m.a NHz)- ether o-~uz-Nnz n t,nz-~;n~-tlnz-nnemyi m-~;~=u~Nnz r-pnenoxyemyi NHz)- ether o-~uz-Nnz n unz-un~-unz nnetnyi m-u~=u~~nz c:n3 NHz)- phenoxyethyl ether o-~uz-Ntiz t-~ unz unz- Memyi m-u~=u~~nz ~n~- ~:ri3-u-NHz)- phenoxyethyl ether o-~uz-~tiz n unz unz- enemy m-~~=~~wnz ~n~- rsn-u-NHz)- phenoxyethyl ether z- z s z P m- z enY
o-z- z s z -P m-~-(=rrn)mnz enY
o-z- z s z -P m- z enY
z- z s z 3- p m_ -~)~Z
eny -o-2 2 3 2 ;- - p eny m_C(=z o-z- z s z n_ eny m- z _p o-z- z s z p mz eny _ o-z- z s z -p m_~-p)~z eny , o-z- z s z -P m- z enY
n-z- 2 3 z j-p m=~z eny _ -o-r 2 3 2 7- p eny m_~-O)~z - -o-z- z s z n_ eny m=C(=O)N~
_p o-z- z s z m P-Cz me z- z s z -a1ll p-me o-z- z s z -am p-C(=NH)NHz me z- z s z 3-am p- z me o-z- z s z ; p- )NHz -am me o-z- z s z n- p- z -am me o-z- z s z m p- z me o-r z 3 z -am p-t.~=a me ~wnz r z s z -am p- z me o-z- z s z 3-am p- )NHz me o-z- z s z 3- p-C(=O)NHz -am me o-r z s z n_ p- z -am me o-z- z s z eny m-C(=NH)NHz -ammo-car oxylic acid O-JUy-Nri2 ~;ti3 z eny m- z -ammo carboxylic acid o-JUq-Nri2 ~;ti3 ~;nz r-pnenyi-ammo m-~.~=mnyvnz carboxylic acid o-JUZ-lVHz 1;t13 l:riz 1.;ri3-pnenyl-ammo m-carboxylic acid o-auz-Nnz ~;ti, trnz 3- m- z -p eny ammo carboxylic acid o-z- z 3 z n- m- z -p eny ammo carboxylic acid o-~uz-wnz uti, unz rnenyi-ammo m- z carooxync acid o-~uz-Nnz Lti3 ~tiz -p m- z eny -ammo CH3carboxylic acid o-JU2-Ntlz Lti, unz r-pnenyi-ammo m-~~=v~rrnz carboxylic acid o-JUZ nz ~:n3 ~atz ~;nj-pnenyi-ammo m-~~=u~mnz N
carboxylic acid o-~uz-Ntiz ~;t13 ~;nz ~n3-u-pnenyi-ammo m-~~=~~mnz carboxylic acid o-z- z s z n- m- z -p eny -ammo car oxyIic acid-o- z- z 3 z et m- z y p epoxy-acetic acid ester o- z- z , z a m- z y -p enoxyacehc acid ester o- z- z 3 z a m- z y -p epoxy-acetic acid ester O-JVz ivriz 3 ~;tiz a m- z y 3-p epoxy-acetic acid ester O-JVz lVriz ~ti3 ~aiz rnemym:rt3-u-pnenoxy- m-~;~=mriyvriz acetic acid ester o-auZ wtiz ~ri3 ~riz nnemyi m-~~=mrywriz ~sn-u-pnenoxy acetic acid ester o-SOZ NHz CH3 CHz Methyl m-C(=U)NHz Yhenoxyacehc acid ester o-SOz-NHz CH3 CHz Methyl m-C(=U)NHz C1-phenoxyacehc acid ester o-SOz-NHz CHj CHz Methyl m-C(=U)NHz >~'-phenoxyacehc acid ester O-JUz-lrtiz ~rij ~riz nnemyi m-~~=vlwriz ~ri3-pnenoxy-acetic acid ester o-JVz NHz 1;t13 ~tiz enemy m-~~=ulwriz Sri;
u-pnenoxy acetic acid ester o-~uz-lVtiz ins ~nz lnemyi m-~t=v~rrriz rsn-u-pnenoxy acetic acid ester o- z- z , z enoxyacehc m- z aci o- z- z 3 z -p m- z epoxy-acetic aci o- z- z s z -p m- PHZ
epoxy- -acetic aci o- 2 2 3 2 ;- p in=~~Nl~jl~Z
epoxy-acetic aci o-SOz-NHz , z 3- m- z -p epoxy-acetic acid o- z- z s z n- m- z -p epoxy acetic aci o- z- z s z enoxyacehc m- z aci o- z- z s z -p m- z enoxyacehc aci o- ~ z , z -p m~(~jN~Z
enoxyacehc aci o- z- z a z 3 m- z p epoxy-acetic aci o- z- z 3 z ;- m- z -p epoxy acetic acid o- z- z s z n- m- z -p epoxy acetic aci o- z- z 3 z enoxye m-~t=wryrrriz ano o- z- z s z -p m- z epoxy-a ano o- r z s z -p m-~:~=mryvriz epoxy-a ano o- z- 2 3 2 ;- p m- z epoxy-a ano o- z- 2 3 2 3- - p epoxy-a uri=C(=NH)NHz ano o- z- z 3 z n- epoxy a m- z -p ano o- z- z s z enoxye m~NHz ano o- z- z 3 z -p m- z enoxye ano o- z- z 3 z -p m-epoxy-a -ano 0- z- 2 3 z g- p m- 2 epoxy-a ano o- z- 2 3 2 ;- - p epoxy- m-a ano -o- z- z s z n- epoxy- a m- )NHz -p ano o- z- z s z ethyl m-C(=NH)NHz pethyl ether o- z- z s z a m- z y -p enoxye y ether o- z- z s z a m- z y -p epoxy-a y ether O-JVZ-Nriy ~ri3 ~riz memyi m- z ~ri3-pnenoxy-ethyl ether o-~uz-lvtiz ~ti3 caiz a m- z y -p epoxy-ethyl ether o-SOz-~I-Iz CH3 z a m- z - y - n--p enoxy ethyl ether O-JUZ-writ t,ri3 ~;tiz lviemyi m-~;(=u)wrtz rnenoxyemyi ether o-r z s z a m- z y -p enoxye y ether o-z- z s z a m- z y -p enoxye y ether o-z- z s z a m- z Y
s-phenoxyethyl ether o-~uz-wtiz s z a m- z Y
phenoxyethyl ether O-JUZ-wriz ~ri3 ~;riz nnemyi m-~(=u)wriz rsn-u-phenoxyethyl ether z- z s z- z P m- z enY
o-z- z s z- z -P m- z ~ enY
0-2 2 3 z-~ 2 -~yi _ o-r z s ~z- z 3- phenyl m_C(=~~z o-2 2 3 2 2 3- - p eny m- z -o-z- z s z- z n_ enyl m=C(-~)~z _p -o-z- z s i z p m-eny _~ _,_._ _ o-z- z a z- z -P m' z enY
o-z- z s r z =phenyl m-C(=O)NFT
o-z- z s z- z s- P m- z enY
--o-z- z s z- z 3- O=phen~ m-C(=O) o-z z a z- z n- eny m- z -p o-z- z s z- z m p- z me o-z- z s i z -am p- NFL
me o-z- z s z- z -am p-C(= z me o-z- z 3 z- z 3-am p- z me o-z- z 3 r z 3- p-C(=NH)NHz -aniline o-z- z 3 z- z n_ p- z _am me o-z- z s r z m p-~(=u)wriz me z- 2 3 2- z -am p- z me -n-r z s z- z -am p- ~~HZ
me z- z s z- z 3-am p- z me o-2 2 3 2- z 3- p-~;(=u)wnz -am me o-z- z 3 z- z n_ p- z _am me o-r z a z- z eny m=C( NH)NHz -ammo-car oxy is acid o-~uz-wtiz ~;rij z- z eny m- z -ammo carboxylic acid o-JVZ-writ t,ri3 Ltiz-~:riz r-pnenyi-ammo m-~(=wri)wriz carboxylic acid o-~uz-wttz ~:ri3 Lriz-~:riz tai3-pnenyi-ammo m-~(=wti)wriz carboxylic acid o-~u2-wriz ~ri3 ~riz-~riz ~ri3-u-pneny m-~(=wri)wriz ammo carboxylic acid o-z- z s z- z n_ m- z _p eny ammo carboxylic acid o-~uz-wriz ~ri3 ~riz-~riz rnenyi-ammo m-~(=u)wriz carnoxync acid o-~u2 riz ~ri3 ~riz-~rlz m-pnenyi-axmno m-~(=u)wriz w carboxylic acid O-JUz riz ~ti3 taiz-~:riz r-pnenyi-ammo m-~:(=u)wriz w carboxylic acid O-JUZ-wriz ~ri3 ~riz-~riz ~ri3-pnenyi-ammo m-~:(=u)wriz carboxylic acid o-~uz-wriz t;ri3 t,riz-~:riz ~ri3-u-pnenyi-ammo m-~(=u)wriz carboxylic acid o-z- 2 3 2- z n-O-pheny m--ammo car oxy is aci o-Oz-z CH3 z- z a m- z iy p epoxy-acetic acid ester o-SUz-NHz 3 CHz-CHz Methyl m-C(=NH)NHz C1-phenoxyacehc acid ester o-z- z 3 CHz Hz Methyl m-C(=NH)NHz C r'-phenoxy-acetic acid ester o-~uz-wriz uri3 uriz-uriz nnemyi m-~(=Nri)Ntiz uri3-pnenoxy-acetic acid ester o-~u2 riz uri3 uriz-uriz Memyi m-u~=Nri)Ntiz w uri3-u-pnenoxy-acetic acid ester O-JUz-wriz , z- z a m- z Y
n--p epoxy acetic acid ester o-~ z s z- z a m- z y enoxyacehc acid ester o-SUz-NHz 3 z- z a m- z y -p enoxyacehc acid ester o-SUz-NHz a z- z a m- z y -p enoxyacehc acid ester o-z- z CH3 CHz-CHz Methyl m-C(=O)NHz CH3-phenoxy-acetic acid ester O-JUz-Ntlz uti3 utiz-~riz enemy m-~~=u)rrriz uri,-u-pnenoxy acetic acid ester o-~u2 tiz ~at3 ~;rtz-~riz nnemyi m-~,~=u)ivriz iv lsn-u-pnenoxY
acetic acid ester o-z- z 3 z- z enoxyacehc m- z aci o-z- z 3 z- z -p m- NFT
epoxy-acetic aci z- 2 3 2 2 -p m-C(= z epoxy-acetic aci o-2 2 3 2- z 3- p m- z epoxy-acetic aci o-z- z s z- z CHa-O-p~erioxy-aceric m-C(=NH)NHz acid o-z- z s z- z n- m- z -p epoxy acetic aci o-z- z a z- z enoxyacehc m- z aci o-z z s z- z Crp m-C(=O)NHz e~cetic acid o-z- z s z- z -p m-C(=O)NHz enoxyacetic acid o-2 2 3 2- z 3- p m- z epoxy-acetic aci o-z- z s z- z j- m-C(=O)NHz -phenoxy acetic--acid o-z- z s z- z n- m- z -p epoxy acetic aci o-z- z s z- z enoxye m- z ano o-z- z s z- z -p m- 2 epoxy-a ano o-z- z s r z -p m-C(=NH)NHz epoxy-a and o-z- z s z- z 3 m- z p epoxy-a ano o-r z a z- z ~n3-u- Pnenoxy-emanoim-~~=mri)mriz o-z- z 3 z- z n- epoxy a m- z -p ano o-z- z s z- z enoxye m- z ano o-z- z s i z -p m-C(=O)NHz enoxyethanol o-r 2 3 2- z -p m- z epoxy-a ano o-z- z s z- z 3-p m- NHz epoxy-a ano o-z- 2 3 2 2 j- p epoxy- m- z - a ano o-2 2 3 2- z n- epoxy-a m- z -p ano o-z- z a z- z a m- riz y p epoxy-a y ether o-~uz-wtiz tJti3 ~tizm:riz nnemym-pnenoxyemy m-~:~=mri)mriz ether o-~uz-ivtiz ~ai3 ~tiz-~riz nnemyi m-~.~=ivri)ivriz r-pnenoxy-emyi ether o-~uz-wriz uri, ~riz-~riz memyi m-u~=ivri)ivriz uri3-pnenoxy-ethyl ether o-~uz-Nriz uri3 ~riz-~riz nnewyi m-ut=wryvriz uri3-u-pnenoxy-ethyl ether o-z- z 3 z- z et m- z y n--p enoxy ethyl ether O-JVZ-lVriz 3 z_ z nnemyi m-c:~=V)wriz rnenoxyemyi ether o_i z s z_ z a m- z y -p enoxye y ether O-JVz-lVriz 3 z- z a m- z y -p enoxye y ether o-~Vz-Nriz l:ri3 l;riz-l:riz enemy m-t,(=V)wriz ~ti3-phenoxyethyl ether O-JVz-lVriz 1:ri3 l:riz-l:riy Melllyll:ri3-V- m-l:(=V)1Vt12 phenoxyethyl ether O_z- 2 3 2_ z a m_ z Y
n_ phenoxyethyl ether o_z- z a z- z-z P m_ z enY
o_2 2 3 2 2_z -p m-eny -.
O_z_ z 3 z- z_z -p m_C~-eny o_z_ z a z_ z-z s_ P m_ z enY
o_r z s z- z-z 3- - p eny m-~;~=~ti)mtiz o_z_ z s z_ z-z n- eny m- z -p - -o-z_ z 3 z- z-z p m-C(=O)~z eny o_z- z s z- z-z _p ~)~z eny O_z- 2 3 z- z-z _p m_C(=O)~z eny --o_z- z s r z-z 3-p m-C(-O)NHz eny o_z- z s z- z-z 3 P enY z _ o_z z s z- z_z n_ eny m- z _p O_z_ z a Y z_z n1 p_ me o_z_ z s z- z-z -am p-~:(=~t~)~tiz me O_z z s z- z-z -am p- z me o_z_ z s z- z z 3-am ~(=NH)NFIz me o_z_ z s z- z-z 3- p- z -am me O-z_ 2 3 z- z-z n_ P_ _am me O_z_ z s z- z z m p_ (=O)~z me O_z- 2 3 2 2_z -~ P_ z me O_z- 2 3 z- z_z -am p- z me o_z- z s z- z-z 3-am p- z me 2_ 2 3 2_ 2_2 3' -anl --.
me 2 2 3 z- z-z n_ p_ z _am me o_z- z s z- z-z eny m-C(=NH)NHz -ammo-car oxy is acid O-JUZ-Ntiz Lti3 laiz tiz-l:rizla-rnenyi-ammo m- z ~
carboxylic acid --o_r z s z_ z-z -P m-C(-NH)NHz enY
-ammo carboxylic acid o-~VZ tiz l;ti3 laiz-laiz-laizl:ri3-pnenyi-ammo m- z tv carboxylic acid O-JUz tlz Lti3 l:riz-l:riz-l:rizl;ri3-V-pnenyi m- z 1v ammo carboxylic acid O-JUz-Ntiz Lri3 ~nz-~ riz-~nz ~sn-V-pnenyi m- z ammo carboxylic acid O-JUz-Nriz 1:ri3 ~-rizWriz_1-riZYrienyl-ammo m-CarDOXyIIC
acid O-JVz-Nriz lai3 l:riz-l;tiz-laizl;i-pnenyi-ammo m- z carboxylic acid O-JVZ-Nriz l;ti3 ~riz-~riz-~-nz r-pnenyi-ammo m-~l=V)r~riz carboxylic acid o-~Vz-lvtlz lat3 l:riz-l:riz-l:rizl;ri3-pnenyi-ammo m-~~=V)~riz carboxylic acid o-JVZ tiz 1x13 1x12-l:riz-l;tlzl;ri3-V-pnenyi-ammo m-~~=VJ~riz carboxylic acid o_z_ z a z_ z_z n- m- z -p eny -ammo car oxy is aci o-z- z s z- z-z et m- z y p ienoxy-acetic acid ester o-r z s z- z-z a m- z y -p enoxyacehc acid ester o-S~-PHz 3 z- z-z a m- z y -p epoxy-acetic acid ester o-~u2 ttz LH3 calz-Ltiz-Ltiz Metnyi m- z N Lti3-pnenoxy-acetic acid ester o-~Uz-Nriz ~H3 c:Hz-~riz-~tiz enemy m- z ~ri3-u-pnenoxy-acetic acid ester o-~uZ ttz cai3 ~;riz-trtiz-Ltiz a m- z N y n--p epoxy acetic acid ester o-SOz-NHz CH3 CHz-CHz-CHz Methyl m- z Yhenoxyacehc acid ester o-SOz-NHz CH3 CHz-CHz-CHz Methyl m-C(=U)NHz C1-phenoxyacehc acid ester o-z- 2 3 2- z-z a m- z y -p enoxyacehc acid ester O-JVZ-NHZ ~:H3 ~aiz tiz-Ltiz Memyi m-~~=uyvriz L trti3-pnenoxy-acetic acid ester o-5u2 tiz LH3 ~tiz-~ty-Ltiz Memyi m-~~=u~mriz N ~ri3-u-pnenoxy acetic acid ester O-JU2-Nri2 Ltl3 LHZ tiZtiz Merry m-~~=u~rVriz L ~ tsn-u-pnenoxy acetic acid ester o-z- z s r r z enoxyacehc m- z aci o-z- z s z r z -p m-C(=NH)NHz epoxy-acetic aci o-z- z s z- r z -p m- z epoxy-acetic aci o-r z 3 2- r z s-P m-C(=NH)NHz epoxy-acetic aci o-z- z s z- z-z 3 m- z -p epoxy-acetic acid o-z- z 3 z- z-z n- m- z -p -epoxy acetic aci o-2 2 3 2- r z enoxyacehc m- =O)NHZ
aci -o-r z s z- z-z -p n~~
enoxyacehc ~~2 acm o-z- z s z- z-z -p m- z enoxyacehc aci o-z- z s z z-2 3- p m- =O)NHz epoxy-acetic aci o-r z ~s CHz-CHz-CHz 3- m- z -p epoxy acetic acid o-z- z a z- z-z n- m- z -p epoxy acetic aci o-z- z 3 z- z-z enoxye m- z ano o-z- z s z- z-z -p m- NHz epoxy-a ano o-z- z 3 2- r z -p m- =NH)NHz epoxy-a ano o-z- z 3 z- z-z 3- p m- z epoxy-a ano o-z- z 3 z z-z 3- - p epoxy-a m- =NIT)NHz ano o-r z 3 z- z-z n- epoxy a m- z -p ano o-z- z ~ i z-z enoxye m- z ano o-z- z 3 z- z-z -p m- z enoxye ano o-r z 3 r z-z -p m-epoxy-a ano o-z- 2 3 2- z-z 3- p rim=C~=O~HZ
epoxy-a ano z- 2 3 2- z-z 3- - p epoxy- m- z a ano o-z- z 3 z- z-z n- epoxy- a m-C~=~)NHz -p ano o-z- z 3 r z-z a m- z y p epoxy-a y ether o-5Vz-Nriz cai, ~tiz-~tiz-~tiz Metnyi m- z ca-pnenoxyeuiyi ether o-5uz Hz c:H3 c:riz-~riz-~tiz Memyi m- z N r-pnenoxy-ecnyi ether o-~u2 Hz LH, ~riz-~riz-~tiz enemy m- z N ~ri3-pnenoxy-ethyl ether o-~u~ ttz ~;ti3 aiz-Ltiz-~aiz memym;ri3-u-pnenoxy- m- z N y ethyl ether o-SOz-NHz CH3 z- r z a m- z y n--p ienoxy ethyl ether o-JVy-1Vr12 lalg ~-tlz-l:riZ-C:tlz Methyl m-l:(=V)Ntlz YnenOXyeTtlyl ether o-z- z s ~-riz-~-riz-~-nz Memyt m-~:(=V)i~riz l:~-pnenoxyemy ether z- 2 3 2- z-z a m- z Y
-p enoxye y ether o-z- z s z r z a m- z Y
s-phenoxyethyl ether o-~Vz-Ntiz ~:ri3 ~:riz-~riz-~;riz Memyi m- z ~ri3-V-phenoxyethyl ether o-JVZ-lVrlz 3 z z-z a m- z Y
n-phenoxyethyl ether o-z- z s z- s P m- z - enY
o-z- z s z- 3 -p m-C~ ~)~z - eny --o-z- z s z- ~ s -phenyl m_C(-~~z -o-z- z s z- ~ 3- p _ eny 2- 2 3 2- 3 j- - p eny m-C
-o-z- z s z- 3 n- eny m-- -p o-z- z s z- s P m~~ O)NHz - enY
o-z- z s z- 3 -p In-C(=O)NHZ
- eny o-z- z s z- 3 -p m-- eny o-z z s z- s 3- p m-C(=O)~z _ enyl o-r z a z- s 3- O-P~eny~ m-C(=O)NHz - - _ z- 2 3 2 3 n_ eny m- -O)~z - _p o-z- 2 3 2- 3 m p-C(=NI~NF
- me o-z- z 3 r 3 -am p-~;(=Nti~~tiz - me -o-z- 2 3 2- , -am P-CON~RHz - me 2- 2 3 2- 3 3 p-l.(=lVr1)1Vt12 - ~ .
me 2 2 3 2- 3 3- p-C(=~)~2 - -anl -me -2- 2 3 2- 3 n- p_C(~H~NH2 - -am me --.
_ 2 2 3 2 3 1 p-~O)~Z
- - me 2 2 3 2- 3 -~ P- 2 - me 2- 2 3 2- g -alll p-l.(=V)1Vr12 - me 2- 2 3 2- 3 3-am p-l.(=V)1Vt12 ' me 2 2 3 2- 3 j- P- 2 - -anl me 2- 2 3 2- 3 n- p-C( - -am me o-r z s z- 3 eny - -ammo-car W .' 1.111.11 oxy m- z is V
acid o-z- 2 3 2- 3 - m-C(=NH)NHz - hen~~no v1 carboxylic acid o-z- z a z- 3 -p m-~~=mry~riz - eny -ammo carboxylic acid o-z- 2 3 2 3 m-C(=NH)NHz s-P~-a~o carboxylic acid o-z- z s r 3 m-C(=NH)NHz - v11 s-~~nyI
ammo carboxylic acid --o-z- z a z- j amino m-C(=NH)NHz - L
V
n--phenyl carboxylic acid o-z- 2 3 2 3 eny m-C(=O)NHz - -ammo carboxylic acid O-JUz-Nriz ~rt3 ~tiz-Sri(-~ri3~-m-pnenyi-ammo m-~(=Vlwriz carboxylic acid O-JUz-Nriz ~ti3 ~riz-Sri(-~rij~-r-pneny-ammo m-~(=Vlwriz carboxylic acid o-z- z s z- 3 a-P m- z - enY
-ammo carboxylic acid o-z- z s z- 3 m- =O)NHz - v11 v' V
-p eny -ammo carboxylic acid o-z- z s z- 3 n- m- z - -p eny -ammo car oxy is aci --o-z- z s z- j et m=~ NH)NHz - y p ienoxy-acetic acid ester o-SVZ Hz s z- s Methyl m- z N - C1-phenoxyacehc acid ester o-SOz-NHz 3 z- s Methyl m- z - F-phenoxy-acetic acid ester O-JVz-NHZ ~ri3 c:riz-~ri~-~ri3~-Memyi m- z ~H3-pnenoxy-acetic acid ester O-JVZ tiz ~ri3 c:riz-pry-~ri3~-Merry m-~~=rrry~riz N ~H3-u-pnenoxy-acetic acid ester o-~u2 Hz LH3 ~riz-pry-~ti3~-Merry m-~~=rrri~Nriz N nn-u-pnenoxy acetic acid ester o-SUz-NHz CH3 CHz-CH(-CH3)-Methyl m- z Yhenoxyacehc acid ester o-OZ=NHz CH3 CHZ -CH3)-Methyl m-C(=U)NHz CH( C1-phenoxyacehc acid ester o-SOz-NHz CH3 CHZ -CH3)-Methyl m- z CH( F-phenoxyacehc acid ester o-SUz-NHz LH3 z- 3 a m- z - y 3-p epoxy-acetic acid ester o-z- z s z- s m-C(=O)NHz - m m a w v a Y
-phenoxy acetic acid ester o-z- z a z- s m-C( ~ jNHz - a.a w a ar v as a Y
n--P
epoxy acetic acid ester o-z- z s z- 3 enoxyacettc m-C(=Nl3jNHz - aci o-i z s r s -p m- NHz - epoxy-acetic aci o-z- 2 3 z- 3 -p m=C(--NH)NHZ
- epoxy-acetic aci o-z- z s r s s- P m-C( NH)NHz - epoxy-aceric acid o-z- z s z- s 3 m- H)NHz - -p epoxy-acetic acid o-z- 2 3 2- 3 n- m-C(=NH)NHz - -p epoxy acetic aci o-z- z s r 3 enoxyacetic m-C(=O)NHz - aci -z- 2 3 2- 3 -p m- z - enoxyacetlc aci z- 2 3 2- s -p m-C(=O)NHZ
- enoxyacehc aci o-z z s z- s 3- p m-C(=U)NHz - epoxy-acetic aci z- 2 3 2- a s- rim-C(=O)NHz - -p epoxy acetic acid o-z- z s r s n- m-C(=V)NHz ' -p epoxy acetic aci o-r z s z- 3 enoxye m-- ano z- 2 3 2- s -p m-C(~NHz - epoxy-a ano o-2 2 3 2 3 -p m- z - epoxy-a ano o-z- z s z- s j- p m- z - epoxy-et ano o-z- z s z- a 5- - p epoxy-a m-C(=NH)NHz - ano o-z- z 3 2 3 n- epoxy a m-~;~=rrrilrrriz - -p ano o-z- z s z- 3 enoxye m- z - ano -z- 2 3 2 3 -p iri=C(=O)NHz - enoxye ano o-z- z 3 z- 3 -p m-- epoxy-a ano o-z- z 3 z- 3 3- p m- )NHZ
- epoxy-a ano o-z- z s z- 3 3- - P epoxy- m-C~ a)NHz - a ano o-2 2 3 2 3 n- epoxy- a m-~:1=a - -p ano ~r~riz o-z z s z- 3 a m- NHz - Y ,J~ ...., p epoxy-a y ether o-2 2 3 2- s a m- )NHz - Y ,_.~ ..
-p enoxye y ether o-z z 3 z- s a m- )NHz - Y ..~ ..
-p epoxy-a y ether o-z- z a z- 3 a m-C(=NH)NHz - Y
P
epoxy-ethyl ether z- 2 3 2 J a m=C(=NH)NHz - Y
;--p epoxy-ethyl ether o-z- z s z- 3 a m- z - y n--p enoxy ethyl ether o-z- z s z- s a m- z - y enoxye y ether o-z- 2 3 2 3 a m- z - Y
-p enoxye y ether o-z z 3 z- s a m- z - y -p enoxye y ether o-z z z- 3 a m-C(=O)~z w.aa ~am.aa~_ Y
-w.aa3_ ~ -ava ua a wa phenoxyethyl ether o-~uz-Ntiz ~ai3 ~nz-~n(-~ti3J-Mecnyi m-~~=ulwnz Win,-u-phenoxyethyl ether o-~uz tiz Win, ~nz-~n~-~n3I-iviemyi m-~~=u~wnz N nn-u-phenoxyethyl ether o-z- z s z- z P m- z - enY
-o-z- z s z- z -p m_ =~)~z - eny o-z- z s z- z -p m-~;(=wn)wnz - eny -o-i z s z- z 3 m- )~
- p eny --o-z- z s z- z s-O- PhenyI m-C(=NH)NHz -o-z- z s z- z n- eny m- z - -p -o-r z s Z_ z p - eny o-z- z s z- z -p ~_~(-O)~z - eny -o-z- z s z- z -p m-C(=O)N)T~
- eny o-z- z s r z s- P m-C~O~FIz - enY
o-r z s z- z a- -P eny m- z - -o-z- z s z- z n- enyI m-C(-O)~z - -p o-z- z s r z m p-C( NH)NHz - me o-z- z s r z -am p-~~=mnyvnz - me o-i z s z- z -am p- )NHz - me o-z- 2 3 2- z j-am p- NHZ
- me o-r z s z- z 3- p-i.~=mnyvnz - -am me o-2 2 3 2- z n- p-~~=wn~wnz - -am me o-r z a z- z m p- ~
- me o-z- z s i z -am p- z - me o-z- z s z z -am P- z - me .
o-z- z s z- z 3-am p- z - me o-z- z s z- z s- p-C(=O)NHz - -am me o-z- 2 3 2 2 n- p_C(-O)~z - -am me o-z- z s z- z eny m- )NHz - -ammo-car ~~ ., oxy is acid o-z- z a z- z eny m-C(=NH)NHz - -ammo carboxylic acid o-z- z s z' z -p m- z - eny -ammo carboxylic acid o-r z 3 z- z j-P m-~~=mnyvn2 - eny -ammo carboxylic acid o-r z 3 z- z j-- -P ~ i,aa~a,aa eny m- z ammo carboxylic acid o-z- z 3 z- z n- m-~:~=mnyvnz - -p eny ammo carboxylic acid o-z- z s z- z eny m-C(=O)NHz - -ammo car oxy is acid o-z- z 3 z- z -p m- =O)NHz - eny -ammo carboxylic acid o-z- z s z- z -p m- _ )NHz - eny -ammo carboxylic acid o-z- z s z- z s-P m- (=O)NHz - enY
-ammo carboxylic acid o-z- z a z- z a~o m- =O)NHz i carboxylic a d o-2 2 3 2- z n- m- 2 - -p eny -ammo car -oxy is aci z- z a rri=C =
- iy z p epoxy-acetic acid ester o-z- z 3 z- z a m- z - y -p enoxyacehc acid ester o-z- z 3 z- z a m- z - y -p epoxy-acetic acid ester o-z- 2 3 2 2 a m- z - Y
3-p epoxy-acetic acid ester o-~uz-wriz Sri, z- z a m- z - y -p epoxy-acetic acid ester o-- -- z ( -~z)--~~yl m-C(=NH)NHz Bn-O-phenoxy acetic acid ester o-SOz-NHz CH3 CHz-CH(-NHz)-Methyl m-C(=U)NHz Yhenoxyacehc acid ester o-SOz-NHz CH3 CHz-CH(-NHz)-Methyl m-C(=U)NHz C1-phenoxyacehc acid ester o-SOz-NHz CH3 CHz-CH(-NHz)-Methyl m- z r-phenoxyacehc acid ester o-~uz-wtiz Lti3 ~tiz-qty-Ntiz~-Memyi m-~~=u~wriz ~ri3-pnenoxy-acetic acid ester O-JUz tiz Lti3 ~;tiz uvtizl-Memyi m- z w ~;ry ~ri3-u-pnenoxy acetic acid ester O-JVz tiz Lti3 ~riz-qty-wtiz~-enemy m-~~=uyvriz w tsn-u-pnenoxy acetic acid ester o-r z 3 z- 2 enoxyacehc m- z - aci o-z- z 3 z- z -p m-C(=NH)NHz ~ - epoxy-acetic acid o-z- z 3 z- z -p m-- epoxy-acetic aci o-z- z s r z 3 p m-C(=NH)NHz - epoxy-acetic aci o-z- z 3 z- z m-C(=NH)NHz - ~.~.
~.
s--Phenoxy=acetic acid o-z- z 3 z- z n- m-C(=NH)NHz - -phenoxy acetic acid o-2 2 3 2- z enoxyacehc m- z - aci o-z- z s z- z -P m- )NHz - enoxyacehc -aci o-z- z s z- z -p m- z - enoxyacehc aci o-z- z s z- z 3- p m-C
- epoxy-acetic aci o-z- z 3 r z s- m-- -P
epoxy acetic acid o-r z s z- z n- m- z - -p epoxy acetic aci o-z- z s z- z enoxye m- )NHz - ano -o-z- z s z- z -p m- 2 - epoxy-a ano o-z- z a z- z -p m-t,~=mryvriz - epoxy-a ano o-r z s z- z 3- p m-- epoxy-a ano o-r z 3 z- z 3 - p epoxy-a m-C( NH)NHz - ano o-z- z s z- z n- epoxy a m-~~=mryvriz - -p ano o-z- z 3 z- z enoxye m=C(=O)NHz - anol --o-z- z a z- z -p m-~~=uyvri2 - enoxye ano o-z- z 3 z- z -p m-- epoxy-a ano o-z- z s z- -~i)-3- p m-C(=O)NHz ( epoxy-ethanol-o-z- 2 3 2- z s- - P epoxy- m- z - a ano o-z- z 3 z- z n- epoxy- a m-- -p ano o-z- z 3 z- z - ma .~ mu m m- )NHz i m m m a y p epoxy-a y ether o-z- z s z- z a m- =NH)NHz - Y
-P
enoxye y ether o-~uz-wriz 3 ~riz-pry-wri2~-a m- z y -p epoxy-a y ether O-JUz-writ ~ri3 ~riz -rrriz)-enemy m-~~=mryvriz Sri( ~ri3-pnenoxy-ethyl ether o-z- z s z- z a m- z - Y
-P
epoxy-ethyl ether - -o_Z~ z 3 2 z - a y m_ n _ _p enoxy ethyl ether o-~u2 riz l:ri3 l;riz y-wriz)-Memy rnenoxyemy m-~~=u)wtiz w 1:r ether O-JUz-1Vr12 1.r13 Lri2-LW-~ri2)-Memyi la-pnenoxyetnyim-Lt=u)ivtiz ether o-~uz-wriz l:ri3 ~riz-ury-r~riz)-nnetny r-pnenoxyemym-ut=u)wriz ether O-JUz-wriz l:ry l:riz-l:ry-Nnz)-Memym:rij- m-~;t=u)Ntiz phenoxyethyl ether o-~u2 tiz ~ri3 l:riz-Sri(-Nriz)-nnemyi 1:n3-u- m- z N
phenoxyethyl ether o-JUZ-Nt12 1x13 l;tlz-lal(-iVtl2)-Memyl tin-u- m-l;~=u)Nriz phenoxyethyl ether o-z- z s z- - n P eny m- z -o-z- z s z- - n -p eny m_C~_~)~z _ _ o-z- z s z- - n -p eny m-_ z- 2 3 2- - n 3-p eny m- z -o-r z s z- - n 3_ _p eny m-CO~z -o-z- z 3 z- - n n_ _p eny m- z -o-z- z s z- - n p eny m-~~=u)wriz -o-z- z s z- - n -p eny m- z _ z- z s z- - n -p eny m-_ o-z- z s z- - n j-p eny m_ )~
-o-r z s z- - n 3- -p eny rn-C~~
-o-z- z s z- - n n_ _p eny m--o-r z 3 z- - n m me p-1:~=r~ri)wriz -o-z- 2 3 2- - n -am me p- z -z- 2 3 2- - n -am me p=C~)~z _ o-r z 3 z- - n 3-am me P-C~
-o-z- z s z- - n j_ _am me p-~~=~ri)~riz -o-z- z s z- - n n- -am me p- z -o-z- z s z- - n i me .. P- z -z- 2 3 2- - n -am me p-_ o-z- 2 3 2- - n -am me p- z -o-z- z s z- - n j-am me p_ z - -o-z- z s z- - n 3_ =~~e p_C~=O)~z -o-r z s z- - n n- -am me p-C( O~PHz -o-z- z s z- - n eny -armno=carboxylicm- )NHz -acid O-JVZ-Nriz lai3 z- - n eny -ammo m- z -carboxylic acid o-~uz-Ntiz lai3 l:riz-l:ry-~sn)-r-pnenyi-ammo m- z carboxylic acid o-JUz-NriZ 1x13 (alz-C:ri(-tin)-1:ri3-prienyl-ammom-carboxylic acid O-~Uz-NriZ lai3 Ltiz-lay-tsn)-3_ _p eny ammo m- z carboxylic acid o-~u2 riz lai, laiz-lay-rsn)-n- -p eny ammo m- z N
carboxylic acid o-~u2 tiz l:rt3 laiz-l:ry-rsn)-rnenyi-ammo carooxyncm-1;~=u)ivriz w acid O-JUz-wtiz lai, l:riz-l:ry-tsn)-l.;i-pnenyi-ammom-~~=u)wriz carboxylic acid O-JUz-Nriz Sri, laiz-l:ry-tsn)-r-pnenyi-ammo m-1:~=u)~riz carboxylic acid O-JUz-wtiz l:ri3 uriz y-~sn)-l:ri3-pnenyi-ammom-~~=u)~riz ur carboxylic acid o-JUz r12 1:ri3 lal2-lJri(-tSn)-1:ri3-u-pneriyl-ammom-1:~=u)lVrlZ
carboxylic acid o-2 2 3 z- - n n- _p eny -ammo m- z ~
-car oxy is aci o-z- z s z- - a m-n y - p epoxy-acehc acid ester o-SOz-NHz 3 z- - a m- z n y - -p enoxyacehc acid ester o-SOz-NHz CH3 CHz-CH(-Bn)-Methyl m- z F-phenoxy-acetic acid ester O-~uz-Ntlz ~rij utiz-uti(-~sn)-Mewyi m-~l=wri)wriz uri3 pnenoxy-acetic acid ester o-~Vz-Nriz Lti, Ltiz-Lti(-tsn)-Merry m-u(=wti)Ntiz uti3-u-pnenoxy-acetic acid ester O-JVz-lVriy :rij utizway-tsnl-Merry m-tJ~=~ri)~riz rsn-u-pnenoxy acetic acid ester o-SOz-NHz CH3 CHz-CH(-13n)-Methyl m-C(=U)NHz Yhenoxyacehc acid ester o-SOz-NHz CH3 CHz-CH(-I3n)-Methyl m-(:(=U)NHz C1-phenoxyacehc acid ester o-SOZ Hz CH3 CHz-CH(-t3n)-Methyl m- z N F-phenoxyacehc acid ester o-z- z 3 r n m_C(=p)~2 - ....
a Y
P
epoxy-acetic acid ester o-z- z 3 z- - a m-C(_O)~2 n Y
- s-:
P
epoxy acetic acid ester o-~uz Hz ~:ri3 z- n a m- z N - y n--p epoxy acetic acid ester o-z- z s z- n enoxyacehc m- z - aci -o-z z 3 z- n -p m- z - epoxy-acehc aci o-z- z 3 z- n -p m-(:(=NH)NHz - epoxy-acehc aci o-z- z s z- - 3 p m-C(=NH)NHz n epoxy-acehc - aci o-r z s r n 3- m- z - -p epoxy-acehc acid o-r z s r n n- m- z - -p epoxy acehc aci o-z- z a z- - enoxyacehc m-C(=O)NH2 n acW
-o-z- z , z- - -p m- z n enoxyacehc - aci o-z- z 3 z- - -p m-n enoxyacehc - aci o-z- z s z- - 3-p iri=C(=O)NHz n epoxy-acetic - acid o-SOz-NHz CH3 CHz-CH(-J3n)-3- m- z -p epoxy acehc acid o-z- z s z- - n- m- z n -p - epoxy acehc aci o-z- z 3 2 - enoxye m- (=NH)NHz n ano -o-2 2 3 2 - -p m- z n epoxy-a - ano o-z- z j z- - -p m-~~=~ri)wriz n epoxy-- a ano o-2 2 5 2- - 3- p m- z n epoxy-a - ano -o-z- 2 3 z- - 3- - p epoxy-ethanol~~NHz n -o-z- z 3 z - n- epoxy a m- z n -p ano --o-2 2 3 2 - enoxye m=C(O)NHz n ano -o-z- z s z- - -p m- z n enoxye - anol o-z- 2 3 z- - -p m- z n epoxy-a - ano o-z- z 3 z- - s- P m-~~=u)~riz n epoxy-a - ano o-z- z s z- - 3 - p epoxy- m- z n a ano -o-z- z s z- - n- epoxy- a m-n -p ano -o-z- z 3 z- - a m- 2 n y - p epoxy-a y ether o-~uz-Ntiz ~ai3 2 - a m- z n y - -p enoxye y ether o-~uz-ivtiz s z- - a m- z n y - -p epoxy-a y ether o-z- z s z- - a m- z n Y
- s-P
epoxy-ethyl ether o-~u2 tiz ~ri3 ~riz-pry-tsn)-enemy m-~~=wri)wriz N ~ri3-u-pnenoxy-ethyl ether o-Z- ~z z- - n a y n_ _p ienoxym- z -ethyl ether o-z- 2 3 2- - n a y enoxye y m- z -ether o-z- z 3 r - n a y -p enoxye m- z - y ether O-JU2-lVri2 3 Y - n a y -p enoxye m- z - y ether o-~uz-Nriz ~rij ~riz-~ri~-rsn~- enemy ~ri3- m-~~=u~r~riz phenoxyethyl ether o-z- z s z- - n a Y 3- m- z -phenoxyethyl ether O-lu2 tiz ~:ri3 ~riz-~ri~-~sn~- nneuryi tsn-u- m-~.~=u~r~riz ~
phenoxyethyl ether O-JUZ-1Vt12 ~:ri, ~aiz-qty-~tiz-pnenyi m-t.~=~tiyvriz COOCH,)-O-JUz-wriz ~ri3 ~riz-Sri(-~riz-m-pnenyi m-~~=~rywriz COOCH,)-O-JUy-1Vt12 l;tlg l:rl2-lal~-1x12-r-pnenyi m-~;~=~ri~r~riz COOCH,)-o-~uz-wriz ~.;ri3 ~riz-~ri~-~riz-~ti3-pnenyi m-~:~=wri~wtiz COOCH3)-o-~u2 tiz ~:ri3 uri2 ri2-3_ _p eny m- z w pry-~
COOCH3)-O-JUy-lVtiz 1:ri3 1:ri2-l;ti~-l;tiz-n_ -p eriy m-COOCH,)-o-2 2 3 2 z- P enY m- z COOCH3)-o-~uz-lvtiz t.ri3 ~;tiz-qty-caiz-m-pnenyi m-~~=u~Ntiz COOCH,)-o-~uz-mttz s z- z- -p eny m- z COOCH3)-o-z- z 3 z- z- 3 P enY ' m- z COOCH,)-O-JUZ-Nri2 1:ri3 lalZ-l;ri(-1;t12-~ti3-u-pnenyi m-~~=u~~riz COOCH3)-O-JVz-Nriz uti3 uriz-pry-uriz-nn-u-pnenyi m- z COOCH3)-o-~uz-~ttz uti, uriz-pry-utiz-Amime p-~~=~ri~~riz COOCH3)-O-JUZ-wriz ~;ri, ~riz-pry-~aiz-~;i-amime p-~~=mryr~riz COOCH3)-O-JUz-wriz uri3 ~riz-pry-~riz r-amime p-~~=r~ry~riz COOCH,)-o-~uZ riz ~;ti3 ~riz riz-~ti3-amime p-~~=r~tyr~tiz ~ ~ti~-~
COOCH3)-o-auz riz ~ri3 ~riz-pry-~riz-~ri3-u-amime p-~~=mryr~riz w COOCH,)-O-JUz riz ~ri3 ~nz-pry-~tiz-rsn-u-amime p-~~=~ryr~tiz N
COOCH3)-O-JUZ-~riz ~;ri3 t~riz-pry-~riz-t~mime p-~:~=u~r~riz COOCH3)-O-JUZ-~riz ~ri3 ~riz-pry-~riz-m-amime p-~~=u~~riz COOCH3)-O-JU2-lVri2 3 2- ~ -am me p- z COOCH3)-o-r z s z- z- 3-am me p- z COOCH3)-o-~uz-Nriz uri, ~riz-pry-~riz-uri3 u-amime p-~~=u~~riz COOCH3)-o-z- z s z- z- n- -am me p- z COOCH,)-o-z- z 3 z- z- eny -ammo-car m- z oxy is COOCH,)- acid o-SU2 Hz c.;H3 CHz-CH(_CHz-CI-Yhenyl-ammo m-C(=NH)NHz N
COOCH3)- carboxylic acid O-JUZ riz ~:ri3 ~;riz-Sri(-~:rizr-pnenyi-ammo m-~~=Nrywriz w COOCHj)- carboxylic acid O-JVz-wriz ~ri3 ~riz-Sri(-~riz-uri3-pnenyi-ammom-~~=NryNriz COOCH,)- carboxylic acid ~-'~U2-~ri2 3 2- z- ~-ris-~-Pnenyi m- z armno COOCH,)- carboxylic acid O-JUz-Ntiz t,ti3 ~riz-pry-t,tiz-tsn-u-pnenyi m-~:~=~ryvriz armno COOCH3)- carboxylic acid o-z- z s z- z- eny -ammo car m- z oxy is COOCH3)- acid O-lV2-Nrlz l;rig 1:r12-lal(-lily-m-pnenyi-ammo m-~~=v~r~riz COOCH3)- carboxylic acid o-~uz-Nriz ~ri3 ~riz-pry-~riz-r-pnenyi-ammo m-~~=~~~riz COOCH,)- carboxylic acid O-JUZ-Nri2 1:ri3 ~riz-t.;ry-~riz-~:ri3-pnenyi-ammom- z COOCH3)- carboxylic acid o-~uz-NHz c:ri3 ~tiz-~:ri(-~tiz-3- -p eny -ammo m- z COOCH3)- carboxylic acid o-lUZ HZ 1;r13 l;tlz i2-tin-U-pneriyl-ammom-l:(=V)lVtlz N l;tl(-l:r COOCH3)- carboxylic acid o-SOz-NHz CH3 CHz-CH(-CHz-Methyl phenoxy-aceticm-C(=NH)NHz COOCH3)- acid ester o-SUz-NHz CH3 CHz-CH(-CHz-Methyl Cl-phenoxyacehcm-C(=NH)NHz COOCH3)- acid ester ri-z- 2 3 2- z a y -p enoxy- m- z acetic COOCH3)- acid ester o-~u2 riz ~ti3 ~riz iz-Memyi ~ri3-pnenoxy-m- z N ~rt~-~r COOCH,)- acetic acid ester o-~uz-Ntiz ~ri3 ~riz-qty-~riz-Memyi Sri,-u-pnenoxy-m- z COOCH,)- acetic acid ester o-~uz tiz ~:ri3 ~rtz-Sri(-~riz-Memyi rsn-u-pnenoxym- z N
COOCH3)- acetic acid ester o-SOz Hz CH3 CHz-CH(-CHz-Methyl Yhenoxyaceticm- z N
COOCH3)- acid ester o-SUZ Hz CH3 CHz-CH(-CHz-Methyl Cl-phenoxyacehcm- z N
COOCH,)- acid ester o-SOZ Hz CHI 2 z- a y -p enoxyacericm- z N
COOCH3)- acid ester o-~uz-Ntiz ~ai3 ~tiz-~tt~-~;ti2 nnemym:ri3-pnenoxy-m-l;(=V)1Vr12 COOCH3)- acetic acid ester o-~u2 tiz uri3 uriz i2 enemy Sri,-u-pnenoxym-~~=v~wriz N pry-~r COOCH3)- acetic acid ester o-~u2 tiz ~.;ti3 Lty~ty-t_;tiz Memyi ~sn-u-pnenoxym-~~=u~r~riz N
COOCH3)- acetic acid ester o-SOz-NHz CH3 CHz-CH(-CHz-Yhenoxyacehc m-C(=NH)NHz acid COOCH3)-o-SUZ Hz CH3 CHz-CH(-CHz-Cl-phenoxy-aceticm-C(=NH)NHz N acid COOCH3)-o-SUz Hz CH3 CHz-CH(-CHz-r-phenoxy- aceticm-C(=NH)NHz N acid COOCH,)-o-SUz-NHz CH3 CHz-CH(-CHz CH3 phenoxy-aceticm-C(=NH)NHz acid COOCH,)-o-SUz-NHz CH3 CHz-CH(-CHZ CHj-U-phenoxy-aceticm-(:(=NH)NHz COOCHj)- acid o-SUz-NHz CH3 CHz-CH(-CHz-tan-U-phenoxy m-C(=NH)NHz acetic acid COOCH3)-o-SUz Hz CHj CHz-CH(-CHZ Yhenoxyacetic m- =U z N acid COOCH,)-o-z- z a z- z- -p enoxyacehc aci ~.~ ,.,~.,.
m-COOCH,)-o-z- z CH3 MHz-CH z- -p enoXyacehc m-C(=O)NHz - acid COOCH3)-o-SOz-NHz CH3 (:Hz-C;H(-CHz-CH3-phenoxy-acehcm-C:(=U)NHz acid COOCH3)-o-SOz Hz C;H3 C;Hz-C;H(-(:Hz-C:H3 U-phenoxy m-C;(=U)NHz N acehc COOCH3)- acid o-~z-Hz CH3 CHz-CH(-CHz Bn-U-phenoxy m-C;(=U)NHz acehc acid COOCH3)-O-JUz-Nriz cai3 unz-uril-uriz-rnenoxyemanoi m-~l=~n)~riz COOCH3)-o-~uz-ivttz Lria z- z- -p epoxy-a ano m- z COOCH3)-O-JUz-Nriz c:rt3 laiz-lail-l:riz--p epoxy- a ano m- z COOCH3)-o-JUz-NHz cal3 r z- 3-p epoxy-a ano m- z COOCH3)-O-JUz-Nriz cal3 z- z- s- . -P epoxy-a m- z ano COOCH3)-o-5U2-NHz 1.113 z- z n- -p epoxy a m- z ano COOCH,)-o-5U2-NHz l;tl3 l;tlz-fall-l;tlz-rnenoxyemanoi m-l:l=u)ivriz COOCH,)-o-5Uz-NHz t;tl3 caiz-latl-catz--p enoxye ano m- z COOCHj)-O-JUz-NHz 3 z- z- -p epoxy-a ano m- z COOCH,)-o-~u2 tiz lai3 laiz-fail-laiz-lai3-pnenoxy-emanoim-1.1=u)ivriz N
COOCH3)-o-SVz-Nriz c:ti3 c:riz-l:ril-lai2 cai3-u-pnenoxy- m-l:l=u)wriz emanoi COOCH,)-o-~Uz-Nriz Lri3 uriz-uril-unz-~sn-u-pnenoxy- m- z emanoi COOCH3)-O-JVz-Ntlz lat3 l:riz-l:ril-l:riz-Merry pnenoxy-emym-l.l=mri)wriz COOCHj)- ether o-~uz-Ntiz lai3 laiz-l:ril-l:riz-enemy la-pnenoxyemyim-l:l=wri)wriz COOCH,)- ether O-JVz-Nriz lai3 laiz-lail-laiz-Merry r-pnenoxy-emyim- z COOCH,)- ether O-JVz-Nriz c:rt3 laiz-fail-l:tiz-a Y 3-P epoxy- m- z COOCH,)- ethyl ether O-JVz-Ntlz lai3 laiz-fail-laiz-Merry ~ri3-u-pnenoxy-m- z COOCH~)- ethyl ether O-JVz-Nriz lai3 l:riz-l:ril-l:rizMeuiyi rsn-u-pnenoxym- z COOCH,)- ethyl ether O-JUz-lVriz lai3 laiz-t_;til-laiz-a y enoxye y m- z COOCHj)- ether o-JVz-Nriz lai3 r r a y -p enoxye m- z y COOCH3)- ether O-JUz-Ntiz l:ri3 unz-uril-uriz-Metnyi r-pnenoxyetnyim-~l=u)wriz COOCHj)- ether o-alJ2lVtiz 1x13 laiz-fall-l:riz-Melllyll.;ri3- m- z COOCH3)- phenoxyethyl ether O-JUz-lVtlz 1;t13 z- z- a y 3- m- z COOCH3)- phenoxyethyl ether O-JVz tlz 1x13 l.rlz-l.;tll-l;riz-MeLllyl tSn-u- m-l:l=V)lvrlz lV
COOCH3)- phenoxyethyl ether o-JVz-iVtiz l;rlg l;tlz-lull-laiz-pnenyl m-l:l=1Vri)lvriz CHz-OH)-O-JUz-iVtl2 1:ri3 1:ri2-l:rll-l=rlz-la-pneny m-l:l=wri)mriz CHz-OH)-o-z- z 3 r x- -p eny m-CHz-OH)-o-~Ux-NHx 1:H3 l;Hx-l;Hl-l:Hx-C:H3-pneriyl m- x CHx-OH)-O-JUx-NHx LH3 ~riz-aril-c:Hx-LH3-U-pnenyl m- z CHx-OH)-o-JUz-NHz s z' z- n- -p eny m- z CHx-OH)-o-~uz Hz ~H3 ~riz-~ril-~riz-pnenyl m- z N
CHx-OH)-o-JUz Hx 1:H3 l:Hx-l:Hl-l:Hx--p eny m- x N
CHx-OH)-o-aux-NHx c:H3 ~riz rix_-p eny m- z aril-~
CHx-OH)-O-JUx-NHx (:H3 t,riz tix-~ti3 pnenyi m-t,l=~~Nrix pail-t, CHx-OH)-O-~Ux-NHx ~:ri3 ~aizw;tyu;Hz-~ti3-u-Pnenyt m- z CHz-OH)-o-5Uz Hx ~H, ~Hx-~Hl-LHZ rsn-u-pnenyi m- z N
CHz OH)-o-~ux-NHz 1:r1, x- z 11i1e p- x CHI OH)-o-z- z s x- z -am me p-C( NH)NHx CHz OH)-o-JVx-NHx 1:H3 x- z- -am me . p- x CHx-OH)-o-5U2 Hx s x- z' 3-am me . p- x N
CHZ OH)-o-5Uz-NHz ~:H3 ~:Hz iz-~:ri3-v-anmne p-~:(=r~nyvrix c:Hl-~a CHz-OH)-o-~Vx-NHx 1:H3 z- x- n- -arid me p- x CHz-OH)-o-5Ux-NHx 3 r z- me p- x CHx-OH)-O-5Vx-NHx C;H3 l;Hx-l:Hl-l;Hx-l:1-anllme p-t_;l=V)i~riz CHx-OH)-o-5Ux-NHx 1:H3 (:Hx-l;Hl-l:Hx_r-am11I1e p- x .
CH2 OH)-O-JUx-NHx l:Hg Calx-l;ril-lair-l;rig-anllllle p- x CHx-OH)-O-JVx-NHx 1:H3 l;Hx-l:ril-l:Hx-l.;tl3-u-anllme p- x CHz OH)-o-~Uz-NHx 1:H3 lalx-fat(-laix-tsn-V-amime p-~,(=vJmriz CHx-OH)-O-5Ux-NHx 1.H3 l,Hz Hx-Ynenyl-allllll0-CarDOXyIICm-l:l=lVt1)lVtlx C.HI-l;
CHx-OH)- acid O-JUx-NHx C:H3 (.;Hz rix-eriy -aIrilno m- x l;Hl-l.:
CHz-OH)- carboxylic acid O-5Ux-NHx C:H3 l:Hz Hx--p eriy -amino m- x l:Hl-l;
CHx-OH)- carboxylic acid O-~Ux-Nrix 1;H3 l:Hz Hx-LH3-pnenyi-ammo m-~(=~ry~riz l:Hl-t;
CHx-OH)- carboxylic acid o-JUx-NHx C:H3 lalz rix-3 -p eriy ammo m- x l:ril-l;
CHx-OH)- carboxylic acid O-5Uz Hx C.;H3 l:Hx-l:Hl-l;Hx-tin-U-prieriyl m- x N aIrilIio CHx-OH)- carboxylic acid o-~u2 Hz LH3 ~riz-~ry-~tiz-rnenyi-ammo cardoxyncm-~(=v~r~rix N
CHx-OH)- acid o-JUz Hx 1;H3 l:rix-l:ril-l:Hx-l:l-prienyl-amlriom- x N
CHx-OH)- carboxylic acid O-~Ux-NHx LH3 t,tizwayuaiz r-pnenyi-ammo m- z CHz-OH)- carboxylic acid o-z- z a z- z- 3-P eny -ammo m-~~=~JNriz CHz-OH)- carboxylic acid o-auz-~tiz ~;ri, ~;riz-~:ry-t_;tiz-~;tij-v-pnenyi-ammom-~a=~~~riz CHz-OH)- carboxylic acid O-JUz-Ntiz ~:ri3 ~:riz-~;ry-t_;tiz-tsn-u-pnenyi-ammom- z CHz-OH)- carboxylic acid o-SOZ Hz 3 r z- a Y p enoxy-aceticm- z N
CHz-OH)- acid ester o-SOz-NHz CHI z- z- a y -p enoxyacehcm- z CHz acid ester OH)-o-SOz Hz CHI z- z- a y -p enoxy- m- z N acetic CHz-OH)- acid ester O-JVZ-Nri2 ~;ty :riz-pry-~;riz memym:ri,-pnenoxy-m-~t=mry~riz CHz acetic acid ester OH)-o-~uz-Ntiz uri3 uriz riz-enemy ~ri3-u-pnenoxy-m- z pry-~
CH2 acetic acid ester OH)-o-~uz-Ntiz ~ti3 ~riz-~ryu:ri2 nnemyi rsn-v-pnenoxym- z CHZ acetic acid ester OH)-o-SO~ Hz CH3 CHz-CH(-CHz- Methyl Yhenoxyacehcm- z N
CHz-OH)- acid ester o-SOZ Hz CH3 CHz-CH(-CHz Methyl Cl-phenoxyacehcm-(:(=U)NHz N
CHz acid ester OH)-o-SOz-NHz CH3 CHz-CH(-CHz- Methyl r'-phenoxyacehcm-(:(=U)NHz CHz-OH)- acid ester O-~uz-Ntiz uri, uriz riz-enemy ~ri3-pnenoxy-m-~t=v~r~riz ury-~:
CHz-OH)- acetic acid ester o-~uz-ivnz t~ty trtiz-tit-~aiz Memyi ~ri3-u-pnenoxym-~.t=v~r~riz CHz acetic acid ester OH)-O-JVZ-NHz ury unz-~ril-uriz-nnemyi rsn-u-pnenoxym-~t=~yvriz CHz-OH)- acetic acid ester o-SOZ Hz CH3 CHZ-CH(-CHz- Yhenoxyacehc m- z N acid CHz OH)-o-SOZ Hz CHj CHz-CH(-CHz- -p enoxy-acetic m- z N aci CHz OH)-o-z- z CH3 CHz-CH(-CHz- F-phenoxy- aceticm-C(=NH)NHz - acid CHZ
OH)-o-Oz-~ CH3 CHZ Hz- CH3-phenoxy-aceticm-C(=NH)NHz CH(-C acid CHZ
OH)-o-Uz-MHz CH3 CHZ Hz- 3- -p enoxy-aceticm- z CH(-C
CHz acid OH)-o-Oz-NHz CHj CHz-CH(-CHz- n- -p enoxy aceticm- z aci CHz-OH)-o-SOz-NHz CHj CHz-CH(-CHz- Yhenoxyacehc m- z acid CHz-OH)-o-Oz-NHz CH5 CHz-CH(-CHz- Cl-phenoxyacehc m- z acid CHz OH)-o-SOz-NHz CH3 CHz-CH(-CHz- F-phenoxyacehc m- z acid CHz-OH)-o-SOZ Hz CH3 CHz-CH(-CHz- 3-p enoxy-aceticm- z N aci CHz-OH)-o-SUz-NHz CH3 CHz-CH(-CHz- (:H3-U-phenoxy m-(:(=U)NHz acetic CHz-OH)- acid o-SOz Hz CH3 CHz-CH(-CHz- J3n-U-phenoxy m-(:(=U)NHz N acetic acid CHz OH)-o-~uz-Nriz ~ti3 ~tiz riz-rnenoxyemanoi m- z pry-~
CHz OH)-o-~uz-Ntiz t_;ti3 ~aiz tizwa-pnenoxy-emanoim-~:~=~ry~riz ~;ty-~
CHZ
OH)-o-~uz-Ntiz ~ai3 Ltiz-gay-~aiZ -p enoxy- a ano m- z CHz-OH)-o-~uz-Ntiz 3 z- z- 3-p enoxy-a ano m- z CHz OH)-o- z z 3 z- z- 3- -p enoxy-a m- z ano CHz-OH)-o-~uz-Nriz c:ri3 uriz-aril-utiz-Iin-u-pnenoxy m-~:l=Nri)Nriz emanoi CHz-OH)-o-~uz-Nriz ~ri3 ~-riz-~nl-~riz-rnenoxyemanoi m-~(=u)wriz CHz-OH)-O-~Vz-Nriz Sri, ~nz-~ril-~nz-~l-pnenoxyemanoim-~l=u)Nriz CHz-OH)-O-JUZ-NHZ Lti3 ~ti2-~til-Lriz-r-pnenoxy-emanoim- z CHz-OH)-o-'uz-Ntiz c;ti, z- Z ~ai3-pnenoxy-emanoim- z CHz-OH)-o-~UZ-Ntlz Lti3 ~:rizwayu:rizw;ti3w-pnenoxy- m-~;(=u)ivriz emanoi CHz-OH)-o- z- z a z- z- n- -p epoxy- m- z a ano CHz-OH)-O-JUz-Nriz ~ai3 ~;tiz-pry-~:riz-enemy pnenoxy-ecnyim-~:(=ivri)ivriz CHz-OH)- ether o-JVZ-Nriz c,ti3 ~ai2-Lti(-~:riz-a y -p enoxye m- z y CHz-OH)- ether o-JVz Nttz ~ti3 ~riz Sri(-~riz-a y -p epoxy-a m- z y CHz-OH)- ether o-JVZ Ntiz ~ri3 ~riz-~til-~riz-a Y 3-P epoxy- m- z CHz-OH)- ethyl ether o-JVZ Ntiz uri3 uriz-uri(-uriz-enemy ~ri3-u-pnenoxy-m-~l=wri)ivriz CHZ OH)- ethyl ether O-JVz-Nriz ~:ri3 ~:nz-~ril-Lriz-Metnyi un-u-pnenoxym-~.l=ivri)ivriz CHz-OH)- ethyl ether O-JUy-Ntl2 Lti3 uti2-~ril-uty-nnemyi rnenoxyemyim-~;(=u)wriz CHz-OH)- ether o-~uz-Nriz ~ri3 ~ri2 ~ril-~riz-Memyi m-pnenoxyemyim-~(=u)ivriz CHz-OH)- ether o-auz-Nriz ~ai3 ~aiz ~ti(-~ai2-Memyi r-pnenoxyemyim- z CHz-OH)- ether o-JUz Nti2 1x13 l:riz l.:ril-l:riy-Metnymal3- m- z CHz-OH)- phenoxyethyl ether O-JUz-Ntiz Lti3 ~ti2-aril-~tiz-enemy ~ri3 u- m- z CHz OH)- phenoxyethyl ether o-JUz NHz Cai3 (aiz-~:ri(-~ai2-a y n- m- z CHz-OH)- phenoxyethyl ether o-auz Nttz ~ai3 ~aiZ t_;til-~aiz-pnenyi m-~.(=ivri)ivriz C(=O)-N-morpholino)-O-~UZ-Nri,_ c.ai3 ~ai2-pail-Ltiz-~;i-pnenyi m-~(=ivri)ivriz C(=O)-N-morpholino)-O-JU2-Nri2 c:ri, ~riz aril-~ri2-r-pnenyi m-~(=ivri)ivriz C(=O)-N-morpholino)-av mW .ai m v.y-w v.m a a v~ a.ya.a o- z- 2 3 2- z a-P enY m- z C(=O)-N-morpholino)-O-JVZ-Ntl2 Lti3 Ltiz-aril-Ltiz-~ti3-u-pnenyi m-~l=Nri)ivriz C(=O)-N-morpholino)-.
o- z- z s z- z- n- m- z -P enY
C(=O)-N-morpholino)-O-~uz-Nriz uti3 utiz-aril-~rizpnenyi m-~(=u)wriz C(=O)-N-morpholino)-o- z- 2 3 2- z- -p eny m- )~Z
morpholino)-o-~uz-mtiz l;ri3 l:rlz-l:rll-caiz-r-phenyl m-l:l=u)lvrlz C(=O)-N-morpholino)-o-~uz-Ntiz l:ri3 ~riz l:ril-lalz-l;ti3-phenyl m-l:l=u)lvrlz C(=O)-N-morpholino)-O-JUZ lVriz 1x13 lain-l.;ril-1x12-1:ri3-V-phenyl m-l:l=V)lVriz C(=O)-N-morpholino)-O-JVz-lVriz 1:r13 l:rlz-l:rll-~tiz-tsn-u-phenyl m-l:l=v)lvrlz C(=O)-N-morpholino)-o-~uz-lvriz l:rl3 l;rl2l;rll-l:rlz-Anllme p-~l=IVrI)lvrlz C(=O)-N-morpholino)-O-JUZ-1Vt12 l;tl3 1:ri2-fail-lainl;l-anllme p-l:l=lVt1)lVri2 C(=O)-N-morpholino)-o-JVZ lvrlz cal3 l;tlz-fail-lalz-r-anllme p-l:l=lvrl)lvrlz C(=O)-N-morpholino)-O-JUZ-Ntl2 1x13 1x12-fail-lain-1x13-aI111me p-l;l=lVt1)lVti2 C(=O)-N-morpholino)-O-lV2-Nti2 lal3 1x12-fall-l;tiz-1x13-u-anllme p-l:l=lVt1)lVtlz C(=O)-N-morpholino)-.
o-JU2 Nrl2 laig C.tl2-l;tll-1x12-t5n-u-anllme p-l:l=IVtl)1Vt12 C(=O)-N-morpholino)-O-5u2-1Vr12 1:r13 1;t12-l;tll-1:r12-Amlme p-l:l=u)iVrl2 C(=O)-N-morpholino)-O-JVZ-Nrl2 l;tlg lalz l:tll-1;t12l:l-anllme p-l:l=u)lvri2 C(=O)-N-morpholino)-O-JU2-NrlZ C.;rl3 1x12-fall-lltly-r-anllme p-l;l=V)lVrlz C(=O)-N-morpholino)-O-JU2-1Vr12 laig 1.112-fail-l;rlz1x13-anllme p-l:l=u)lvtlz C(=O)-N-morpholino)-o-aVz-lvtlz c:rl3 l:riz-l;ril-l:rizl:rij-u-anllme p-l:l=v)lvriz C(=O)-N-morpholino)-z- z s z- z- p- =O)NHz is v . w,l n- -and me -C(=O)-N-morpholino)-o-~uz-lvtlz 1x13 lalz-~ril-1-rlz-rnenyl-ammo-carooxyncm-l:l=lvti)lvrlz C(=O)-N- acid morpholino)-o-~uz-lvtiz 1x13 lalz-l;tll-~riz-1:1-rnenyl-ammo m-l:l=lrrl)lvrlz C(=O)-N- carboxylic acid morpholino)-o-~uz lvtlz lai3 lalz-loll-lalz-r-phenyl-amino m-l:l=lvrl)lvrlz C(=O)-N- carboxylic acid morpholino)-O-JUz iVri2 l:rig 1:ri2-l:rll-l;rlz-lalg-phenyl-ammom-l;l=lVr1)lVri2 C(=O)-N- carboxylic acid morpholino)-o=Sz- z ~3 z- r m=C~ NHjIVHz v a m .m v a a m r _p eny amino -C(=O)-N- carboxylic acid morpholino)-O-JUZ-~riz ~;ri3 ~riz-~:ri(-~;riz-~n-u-pnenyi ammom-~;t=~ryvriz C(=O)-N- carboxylic acid morpholino)-o-~uZ riz Sri, ~riZ pry-~riz-rnenyi-ammo carnoxyncm-~~=v~~riz N
C(=O)-N- acid morpholino)-o-~uz-Ntiz ~ri3 ~tiz-pry-caiZm-pneny-ammo m-~~=u~Nriz C(=O)-N- carboxylic acid morpholino)-O-lVZ-lVriz l:rig l;riz-l;ri(-l:riz-r-pnenyi-ammo m-~,~=~Jr~riz C(=O)-N- carboxylic acid morpholino)-o-~uz-mtiz ~;ti3 ~aiz-Lty-trtiz-Lri3-pnenyi-ammom-~;~=u~Ntiz C(=O)-N- carboxylic acid morpholino)-O-JUZ riz ~:ri3 ~;riz-~:ri(-~;riz-Sri; v-pnenyi-ammom-~,~=ulr~riz ~
C(=O)-N- carboxylic acid morpholino)-O-JUZ-1Vt12 1:ri3 uriz-~;ry-~riz-nn-u-pnenyi-ammom-~~=v~~riz C(=O)-N- carboxylic acid morpholino)-o-SOZ Hz CHj CHZ CH(-CHz-Methyl phenoxy-aceticm-(:(=NH)NHz N
C(=O)-N- acid ester morpholino)-o-SOz-NHz CH3 CHz-CH(-CHz-Methyl Cl-phenoxyaceticm-C;(=NH)NHz C(=O)-N- acid ester morpholino)-o-SOz-NHz CH3 CHz-CH(-CHzMethyl 1:-phenoxy-m-(:(=NH)NHz acetic C(=O)-N- acid ester morpholino)-o-~u2 Hz cai3 caiz ~;ti(-~aiz-Mecnyi ~tt3 pnenoxy-m-~:~=~ry~riz N
C(=O)-N- acetic acid ester morpholino)-o-~u~ Hz cai3 ~;ttz-jai(-caiz-Memyi ~ti3-u-pnenoxy-m-~:~=mry~riz N
C(=O)-N- acetic acid ester morpholino)-O-JVZ-iVri2 Lti, ~;tiz-t.ry-~riz-Memyt tsn-u-pnenoxym-l,(=lVt1)lVtlz C(=O)-N- acetic acid ester morpholino)-o-SOz-NHz CH3 CHz-CH(-CHz-Methyl Yhenoxyacehcm-C(=U)NHz C(=O)-N- acid ester morpholino)-o-SOz-NHz CH3 CHz-CH(-CHz-Methyl Cl-phenoxyacehcm-C(=U)NH_z C(=O)-N- acid ester morpholino)-o-SOz-NHz CH3 CHz-CH(-CHz-Methyl )~'-phenoxyaceticm-(:(=U)NHz C(=O)-N- acid ester morpholino)-o-~u2 tiz Lti3 ~aiz gay-~aiz-enemy ~ti3-pnenoxy-m-~;1=ul~riz N
C(=O)-N- acetic acid ester morpholino)-O-JVz-NriZ ~ti3 uriz-~:ry-urizMemyi ~ri3-u-pnenoxym-~~=a lr~riz C(=O)-N- acetic acid ester motpholino)-o-5uz-NHz Lti3 uriz-ury-~ry-Metnyi nn-u-pnenoxym-~~=~lr~tiz C(=O)-N- acetic acid ester morpholino)-o-z- z CH3 CHz-CH(-CHz-Phenoxyacehc m- z acid C(=O)-N-more o mo o-SUz-NHz CH3 CHZ-CH(-CHz-Cl-phenoxy-aceticm-C(=NH)NHz acid C(=O)-N-morpholino)-o-SUz-NHz CH; CHz-CH(-CHZF-phenoxy- aceticm-C;(=NH)NHz acid C(=O)-N-morpholino)-o-SUz-NHz CH3 CHz-CH(-CHZCH3-phenoxy-aceticm-C(=NH)NHz acid C(=O)-N-moipholino)-o-SOz NHz CH3 CHz CH(-CHz-CH3-U-phenoxy-aceticm-C(=NH)NHz C(=O)-N- acid morpholino)-o-SUz-NHz CH3 CHz-CH(-CHz-Bn-U-phenoxy m-C:(=NH)NHz acetic acid C(=O)-N-morpholino)-o-SOz-NHz CH3 CHz-CH(-CHz-Yhenoxyacehc m-C:(=U)NHz acid C(=O)-N-morpholino)-o- Oz-NHz CH3 CHz-CH(-CHz-Cl-phenoxyacehc m-t:(=U)NHz acid C(=O)-N-morpholino)-o-SOz-NHz CH3 CHz-CH(-CHzr-phenoxyacetic m-C;(=U)NHz acid C(=O)-N-morpholino)-o-SOz-NHz CH3 CHz-CH(-CHZCH3 phenoxy-aceticm-(:(=U)NHz acid C(=O)-N-morpholino)-o-SOZ-NHz CH; CHz-CH(-CHzCH3 U-phenoxy m-C(=U)NHz acetic C(=O)-N- acid morpholino)-o-SOz-NHz CH3 CHz-CH(-CHz-tan-U-phenoxy m-C:(=V)NHz acetic acid C(=O)-N-morpholino)-o-~u2 NHz C:H3 ~;Hz ~;H(-~aiz-rnenoxyemanol m-t,l=Nri)r~riz C(=O)-N-morpholino)-o-JUz-Nriz (.:H3 l;tlz-~atl-~atz-~;1-pnenoxy-emanoim-~;l=~ryririz C(=O)-N-morpholino)-O-JUz NHZ C:H3 l:Hz-l:Hl-lalz-r-prienOXy- eLllanolm-l;l=1Vri)iVtiz C(=O)-N-morpholino)-O-JU2-Ntl2 Lris ~'ri2-~-ril-~'riz'~-n3-pnenoxy-emanoim-~.l=mryvriz C(=O)-N-morpholino)-o-~uz-NHz ~ri3 ~riz-~ry-~ri2-~-ti3-v-pnenoxy-eman0lm-Ll=lVri)lVriz C(=O)-N-morpholino)-o-~uz-NHz ~;H3 ~;tlz ~ail-Lty-tsn-u-pnenoxy m-~:l=mryvri2 emanot C(=O)-N-morpholino)-O-JVZ-NHZ LH3 ~;tizw;til-~tiz-rnenoxyemanoi m-~l=u)~ri2 C(=O)-N-morpholino)-o-~u2-NHz LH3 ~alz-fail-LHz-~a-pnenoxyemanolm-~l=V)ivriz C(=O)-N-morpholino)-o-~uz NHz ~:H3 ~ai2-Ltil-t,tiz-r-pnenoxy-emanoim-Ll=u~~riz C(=O)-N-morpholino)-o- z- 2 3 2- z- 3-p epoxy=a ano m- =O NHz morpholino)-o-~uz-Nriz tai, c:riz-c:nl-~riz-Lna-u-Pnenoxy- m-~:l=u)r~riz emanoi C(=O)-N-morpholino)-O-JUZ-Ntlz c:ri3 Lriz-Lnl-Lriz-~n-u-pnenoxy- m-ul=u)Ntiz emanoi C(=O)-N-morpholino)-O-JVZ-Nriz c:rij caiz-tail-t,tiz-Memyt pnenoxy-emyim-t.l=mti)~tiz C(=O)-N- ether morpholino)-O-lVz-Ntiz 1x13 1x12-l;ril-l;riz-enemy ca-pnenoxyemym-i:l=mriJ~riz C(=O)-N- ether morpholino)-o-DVz-Nriz c:ri3 Ltiz Ltil-caiz-nnemyi r-pnenoxy-emyim-c:l=wri)wriz C(=O)-N- ether morpholino)-o-JVz-Nriz c;ti; ~aiz-tail-caiz-Memy c:ri3 pnenoxy-m-c:l=~ri)~riz C(=O)-N- ethyl ether morpholino)-o-JUz ivtiz cai3 ~a12-tail-~;tiz-Memyi c:rt3-u-pnenoxy-m-~;l=ivri)Ntiz C(=O)-N- ethyl ether morpholino)-o-JVz-Ntiz c:ri3 caiz-cail-caiz-enemy tsn-u-pnenoxym-c.l=mri)r~riz C(=O)-N- ethyl ether morpholino)-o-5uz lvtiz cai3 uttz-uty-catzMemyi rnenoxyemyim-c:l=u)wriz C(=O)-N- ether morpholino)-o-~uz-lvtiz t;tt3 cai2 c:ril-LtizMemyi ca-pnenoxyemyim-c:l=u)r~tiz C(=O)-N- ether morpholino)-o-JUz-Nriz ~;ti3 caiz-tail-caiz-Memyi r-pnenoxyemyim-~:l=u)ivriz C(=O)-N- ether morpholino)-o-JUz-lVri2 1x13 1x12-lJtil-l:rlz-Memy1 t;tt3- m-t;l=u)iVrl2 C(=O)-N- phenoxyethyl ether morpholino)-O-JUz-lVriz Lti3 caiz tail-caiz-nnemyi ~ti3-u- m-~:l=u)r~riz C(=O)-N- phenoxyethyl ether morpholino)-o-~uz tvtiz c:ti3 ~:riz-c:ril-caiz-enemy rsn-u- m-c:l=u)mriz C(=O)-N- phenoxyethyl ether morpholino)-o-JUz-Nriz cai3 r z- P enY m- z CHz-S(O)z-CH3 O-JUz-Nriz s z- z- -p eny m- z CHz-S(O)z-CH3 O-JUZ-Ntl2 cat, catz-~:ril-caiz-r-pnenyt m-t,l=wri)~riz CHz S(O)z-CH3 o-~uz-Nttz tai, c:riz-c.ril-c:riz-~ti3-pnenyi m- z CHz-S(O)z-CH3 o-~uz-tvttz c,ti3 uriz-aril-c:rizc:ri3-u-pneny m-~l=mti)mriz CHz-S(O)z-CH3 o- z- z s z- z- n- -p eny m- z CHz-S(O)z-CH3 O-JUz-Nri2 cai3 c:riz-~:ril-uriz-pnenyi m-~l=u)wriz CHz-S(O)z-CH3 o-JU2-Ntlz 1.113 ljtlz-fail-lalz-(_:1-prienyl m-t=l=u)lVtiz CHz S(O)z-CH3 o-~uz Nriz tai, c:riz-c:ril-~rizr-pnenyi m-c:l=u)wriz CHz-S(O)z-CHj 1\ 1i-J
o-r z s r z- 3-p m- z enY
CHz-S(O)rCH3 o-JUz Hz 3 z- z- s- m- z N -p enY
CHz-S(O)z o-SUz-NHx 3 r z- n- m- x -p eny CHz-S(O)z-CH3 o-SUx-NHx C:H3 (:Hx-fail-C:Hx-Anllme p-l:l=1Vri)lVtlx CHz-S(O)z-CH3 o-SVZ Hx LH3 LHz LHl-~Hz_-am p- z N me CHz-S(O)z-CH3 o-SUZ Hx C;ri~ C:Hx-(.;Hl-c:Hx_-and p- x N me CHz-S(O)z o-SUx-NHz LH3 c:H2 LHl-c:Hz-3-am p- z me CHx-S(O)x-CH3 o-SUz Hx 1:H3 C:Hx-l;Hl-l;Hz1:H3 p- x N U-arillme CHx-S(O)z-CH3 o-JUx-NHx 1;H3 C:Hx-l;Hl-l;Hx-t5n-V-arillme p- x CHz-S(O)z-CH3 o-JUx-NHx 1:H3 lair-~atl-l:tix-Anllme p- x CHz-S(O)z-CH3 o-JVx-NHx 1;H3 lair-fail-~alx-t:1-anlnne p- x CHz-S(O)z-CH3 o-~Vx-NHx CJH3 l:Hz l:Hl-l;Hz_-am p- x me CHz-S(O)rCH3 o-JUx-NHx C:H3 i x- 3-am p- x me CHz-S(O)z-CH3 o-5Ux-Nriz s r r 3- p- x -am a CHz S(O)z-CH3 o-~Uz-Nrix 1;H3 l:Hx-l:Hl-l:Hx-ri_ p- x -an1 me CHx-S(O)z-CH3 o-~Vz-NHz ~:H3 LtlzW allW eny m- z a1z- -ammo-car oxy is CHI S(O)z-CH,acid o-5Uz Hz c:H3 LHz-t.Hl-LHZeny m- z N -ammo CHz-S(O)z-CH,carboxylic acid O-~Vx-NHx ~:H3 Ltizmay-Ltiz-r-pnenyi-ammo m-~;~=mryvriz CHz-S(O)z-CHjcarboxylic acid O-JVx-NHx 1:H3 l;Hx-l;Hl-(.;Hx-1;t13-pnenyl-ammo m-lj(=lvri)lvttx CHz-S(O)z-CH3carboxylic acid o-5uz-NHx c~H3 LHx-~;Hl-~;Hz-~:ri,-u-pnenyi m-t,l=mryvrix ammo CHx-S(O)x-CH,carboxylic acid o-5Ux-NHx C:H3 l:Hz l:Hl-l;Hx-t5n-V-prienyl m- x ammo CHz-S(O)z carboxylic CH3 acid o-~u2 Hx LH3 uHx-~Hl-uriz-rnenyi-ammo m-~~=~~wriz N carnoxync CHz S(O)z acid o-5Uz Hx c:H3 ~:HZ c:Hl-t.Hz-~a-pnenyi-ammo m-~l=vyvrix N
CHx-S(O)z-CH3carboxylic acid o-z- z s z- z- -p m- z eny -ammo CHz S(O)z-CH3carboxylic acid O-5U2 Hx C:H3 l.:Hx-l;Hl-l:Hx-1;H3 m-l;l=U)iVrix N pneriyl-ammo CHz-S(O)x-CH3carboxylic acid o-~u2 Hz ~:H3 t_;tiz-~tyu;tizw;ri3 m- x N m-pnenyi-ammo CHz S(O)z carboxylic CH3 acid o-~uz-NHx LH, LHZ c:Hl-MHz-tsn-u-pnenyi-ammo m- z CHz S(O)x-CH3carboxylic acid o-SOx-NHz CH3 CHz-CH(-CHz-Methyl m-C(=NH)NHz phenoxy-acetic CHz S(O)z acid CH3 ester o-SOz Hx CH3 CHZ CH(-CHx-Methyl m-C(=NH)NHz N Cl-phenoxyacehc CHz S(O)z-CH3acid ester o-SOx-NHx CH3 CHz-CH(-CHz-Methyl m- z r-phenoxy-acetic CHz S(O)Z acid CH3 ester o-tux-NHx ~ai3 taiz-t_;ttl-~tiz-Memym;ri3-pnenoxy- m- z CHz-S(O)x-CH3acetic acid ester o- z- z a z- z- et y 3- -p epoxy-m-CHz-S(O)z-CH3acetic acid ester o-~uz Ntiz ~n3 Ltiz-qty-~aiz-Metnyi tsn-u-pnenoxym- z CHz-S(O)z-CH,acetic acid ester o- z- z CHs z- z- a y enoxyacehc m- z CHz-S(O)z-CH,acid ester o- Z z CH3 CHz-CH(-CHz-Methyl Cl-phenoxyacehcm-C(=U)I
HZ
CHz-S(O)z-CH3acid ester o- Z z - CH3 z- z- a y -p enoxyacehcm- z J V 1 '111 CHz-S(O)z-CH3acid ester o-JUZ-Nri2 Ln3 ~:nz-~nl-~;nz-Memy ~n3-pnenoxy-m-~;l=vyvnz CHz S(O)Z acetic acid ester CHj O-JVZ-Nti2 Lti, ~aiz-~nl-~nz-a Y s- -p epoxy m- z CHz-S(O)z-CH3acetic acid ester o-~uz-ivnz Ln3 trnz-~ryu:nz-memyi isn-u-pnenoxym-~.l=vyvnz CHz-S(O)z-CH3acetic acid ester o-SOz-NHz CHj CHz-CH(-CHz-Yhenoxyacehc m-C(=NH)NHz acid CHz-S(O)z-CH3 o-SOz-NHz CH3 CHz-CH(-CHz-Cl-phenoxy-acehcm-C(=NH)NHz acid CHz-S(O)z-CH3 o-SOz-NHz CH3 CHz-CH(-CHz-1~-phenoxy- aceticm-(:(=NH)NHz acid CHz-S(O)z-CH3 o-SOz-NHz CH3 CHz-CH(-CHz-CH3 phenoxy-acehcm-C(=NH)NHz acid CHz-S(O)rCH3 o-S02 NHz CH3 CHz-CH(-CHz-3- -p epoxy-acehcm- z CHz-S(O)z-CH3acid o-SOZ NHz CH3 CHz-CH(-CHzn- -p epoxy acehcm- z aci CHz-S(O)z-CH3 o-SOz-NHz CH3 CHz-CH(-CHz-Yhenoxyacehc m- z acid CHz-S(O)z-CH3 o-SOZ-NHz CH3 z- Z -p enoxyacehc m- z aci CHz-S(O)z-CH3 o-SOz NHz CH, z- z- -p enoxyacehc m- z aci CHz-S(O)z-CH3 o-SUz-NHZ CH3 CHz-CH(-CHz-CH3 phenoxy-acehcm-(:(=U)NHz acid CHz-S(O)z-CH3 o-SOZ-NHz CH3 CHz-CH(-CHz-3 -p epoxy acehcm- z CHz-S(O)z-CH3acid o-SOz-NHz s r r n- -p epoxy acehcm- z aci CHz-S(O)z-CH3 o-~uz-Ntiz uti, utiz-~nl-~nz-rnenoxyemanoi m-~;(=wn)wnz CHz-S(O)z-CH3 O-JVZ-Nriz Lti3 ~tiz-~ry-~nz-m-pnenoxy-emanoim- z CHz-S(O)z-CH3 O-JUy-1Vt12 Lti3 unz-~nl-~nz-r-pnenoxy- emanoim-~l=wn~wnz CHz-S(O)z-CH3 o-~uz-Ntiz un3 unz-~nl-~nz-~n3-pnenoxy-emanoim-~l=mn~wn2 CHz-S(O)z-CH3 o-JVZ-lVriz ~:n3 ~nz-~nlw;nzw:n3-u-pnenoxy-emanoim-~:l=~n~~nz CHz-S(O)z O-JUz-Nnz ~:n3 ~-riz-~nl-~nz-~n-~-pnenoxy m-~,l=mnyvnz emanoi CHI S(O)z O-JVz-Nri2 ~n3 ~nz-~nl-~nz-enoxye ano m- z CHz S(O)z-CH3 O-JUz-Nnz Lri3 L'ri2-L'ril-L'ri2--p enoxye ano m- z CHZ S(O)z-CH3 o-~uz-Nnz uti3 ~nz-~nl-unz-r-pnenoxy-emanoim-~l=u~wnz CHz-S(O)z-CH3 o- z- z s z- z- 3-p epoxy-a ano m- z CHz-S(O)z-CH3 o-JVz 1Vr12 1.t13 ~-nr~-nl-~nz-~-ris-~-pnenoxy-m-~:l=vyvnz emanoi CHz-S(O)z-CH3 o- z- z a z- z- n- -p enoxy- m-~l=V~Nriz a ano CHz-S(O)z-CH3 O-JUz-Ntlz Lti3 caiz-~til-caiz-iviemyi pnenoxy-emyim-~l=Nri~Nriz CHz-S(O)z-CH,ether O-JUz-Nriz Lti3 ~tiz-~til-Lti?iviemyi m-pnenoxyemyim- z CHz-S(O)z-CH,ether o-~uz-Nttz ~a13 caiz-~;til-~;riz-iviemyi r-pnenoxy-etnyim- z CHz-S(O)z-CH,ether o-5uz-Nrlz c.;ti3 Ltiz-Ltil-Ltiz-iviemyi Lti3-pnenoxy-m- z CHz-S(O)z-CH3ethyl ether O-~uz-Nriz Lti3 ~ttz-~til-~tiz-ivietnyi ~ri3-V-pnenoxy-m- z CHz-S(O)z-CH,ethyl ether o-JUz-Nttz cal3 z- ~ a y n- _p enoxy m- z CHz S(O)z-CH3ethyl ether O-JUZ-Ntlz ~a13 z- r a y enoxye y m- z CHz S(O)z-CH3ether O-JVz-Nriz l~tij z- z- a y -p enoxye m- z y CHI S(O)z-CH,ether O-JUz-Ntiz ~ai3 Ltiz-t,til-Ltiz-ivietnyi r-pnenoxyemyim-~,l=uyvriz CHz-S(O)z-CH,ether o-JUz-Ntiz 1;t13 laiz-fail-l:rlz-nnecnym;ri3- m- z CHz S(O)z-CH3phenoxyethyl ether O-JVz-Ntlz l;tl3 l;tlz-fall-(alz-lVleTilyi 1jt13-u-m-l;l=V)lVriz CHz-S(O)z-CH3phenoxyethyl ether o-JU2 Nttz ~ai3 Lti2 ~;til-t;tiz-miemyi tsn-V- m-~l=vyvriz CHz-S(O)Z phenoxyethyl CH, ether o-~u2 Ntlz Lti3 cai2 Ltil-~tiz-pnenyi m-~l=Nri~Nriz hexane)-o-~uz Ntiz Lti, ~tiz ~ttl-~riz-~i-pnenyi m- z hexane)-O-JVy-Ntiz 1x13 laiz-fall-l:riz-r-pnenyi m- z hexane)-O-JUz-NHz 1;ri3 lalz-fail-lalz-3 p eriy m- z hexane)-O-JVz-Ntiz lal3 lalz-fall-l:riz-1x13 u-pnenyi m- z .
hexane)-o-JVz-Ntlz l;tl3 z- z- n- -p eny m- z hexane)-O-JUZ-NtiZ 3 r r P enY m- z hexane)-o-~uz Ntlz s z- z- -p eny m- z hexane)-O-JUz-Nriz , 2- z- -p eny m- z hexane)-o-auz-Ntiz ~ai3 Ltl2 pail-~tiz-~:ri~-pnenyi m-~l=vyvriz hexane)-o-~u2 NtiZ 1x13 z z- 3- -p eriy m- z hexane)-o-~uz Ntiz uti3 ~riz uril-~riz-rsn-v-pnenyi m- z hexane)-o-~u2 Nriz l;ri, l.atz-~;til-~;ttz-Aniime p-~:l=mtiyvrtz hexane)-O-JUz-Ntiz ltij l:riz-l:ril-l.rizl;i-amime p-l;l=lVr1)lvriz hexane)-O-JUz-Niiz ~-ri3 ~-ri2-~-ril-~'ri2-r-anllme p-1.1=lvri)lVtiz hexane)-o-~uz-Ntiz ~ti3 ~tiz tail-~riz-~:ri3-aniime p-~l=Nriyvriz hexane)-O-lUz-Ntlz lalg l;tlz-l;tll-l:riz-C.ri3 u-anlllllep-l;l=lVriJlvriz hexane)-O-JUz-Nriz 3 z- z- n- -am me p- z hexane)-o-z- z s z- z- m me p- z u' V~111 hexane)-O-JUZ-NHZ C;H3 l;Hz-l:H(-l;Hz-l:l-amlme p-l;(=V)Nrlz hexane)-o-~Uz-Nriz l,ti3 (.,HZ-t,H(-I.HZ-r-amime p- z hexane)-o-~uz-NHz c:ri3 ~tiz-Sri(-~HZ- ~ti3-amime p-~(=u)Nriz hexane)-o-JUz-NHz ~H3 MHz rlz-~H3-u-amime p-~(=u)Nriz ~H(-~
hexane)-O-JUz-NHz 1:H3 l;tlz-lal(-lalz-t5ri-u-anllme p-l:(=U)NHz hexane)-o-JUz-NHz ~;H3 t.Hz-c:H(W;Hz-rneny-ammo-carooxyucm- z hexane)- acid o-~Uz Hz LH3 uHz-uri(-utiz-m-rnenyi-ammo m-~(=Nri)Nriz N
hexane)- carboxylic acid O-JUz Hz c:H3 MHz-~H(-~HZ- r-pnenyi-ammo m- z N
hexane)- carboxylic acid o-JVz-NHz ~;H3 ~:rtz-~:r1(-~;tiz-j-p eny -ammo m- z hexane)- carboxylic acid o-~u2 Hz ~;H3 ~:Hz-~:H(-~;H2 3- -p eny ammo m- z N
hexane)- carboxylic acid o-~Uz-NHz c:H3 LHz-LH(-Ltiz-tsn-u-pnenyi m- z ammo hexane)- carboxylic acid o-5Uz-NHz c:H3 ~ttz-~Hl-~HZ- eny -ammo car m- z oxy is hexane)- acid o-5Uz-NHz (:H3 c:Hz-LH(-LHZ- ~a-pnenyl-ammo m- z hexane)- carboxylic acid O-5Uz-NHZ C;H3 (:HZ-l:H(-laiz-r-prieriyl-ammo m-hexane)- carboxylic acid o-5V~ Hz t;H3 c:Hz-LH(-LHZ ~t13-pnenyl-ammom- z N
hexane)- carboxylic acid o-5Vy-NHy C:H~ C;ri2-l:ri(-lalz-1:H3-u-pnenyl-ammom-l:(=V)Nriz hexane)- carboxylic acid O-JVZ-NHZ C:H3 C:Hy-l:H(-lal2-tSn-V-prieriyl-ammom-hexane)- carboxylic acid o-z-NHz CH3 CHZ Hz- Methyl phenoxy-aceticm-C(=NH)NHz CH(-C
hexane)- acid ester o-SOz-NHz CH3 CHz-CH(-CHz- Methyl Cl-phenoxyacehcm-(:(=NH)NHz hexane)- acid ester ~-~z Hz ~3 CHz-CH(-CHz- a y _p enoxy- m- z N acetic hexane)- acid ester o-5Uz-NHz ~:H3 LHZ-~H(-~tiz-Metnym:H3 pnenoxy-m- z hexane)- acetic acid ester o-JUZ Hz C:Hj lalz-l:H(-lalz-lVieLnyl l=rig-U-pnenOXy-m- y N
hexane)- acetic acid ester o-~Vz Hz C:H3 lalz-l:H(-l:Hz-a y n_ -p enoxy m- z N
hexane)- acetic acid ester o-r z 3 - CHz-CH(-CHz- a y enoxyacehc m- z hexane)- acid ester o-SOz-NHz CHj CHz-CH(-CHz- Methyl Cl-phenoxyacehcm- z hexane)- acid ester o-z- z j CHz-CH(-CHz- Methyl r'-phenoxyacehcm- z hexane)- acid ester o-5U2 Hz t;H3 MHz-~H(-~HZ- nnemyi ~H3-pnenoxy-m- z N
hexane)- acetic acid ester o-~Uz-NHZ t;H3 LHz-~H(-~riz-Metnyi ~H,-u-pnenoxym-~(=u)mriz hexane)- acetic acid ester o-JUz-NHZ C:H3 1x12-l;tl(-C;tl2-Methyl tSn-u-prienOXym-l:(=V)lVri2 hexane)- acetic acid ester o-z-NHz CHj CHz-CH(-CHz- Yhenoxyacehc m-(:(=NH)NHz acid hexane)-o-2- Z a z- z- -p epoxy-aceric aci v~ a.aa~.a m-hexane)-o-r z 3 z- z- -p epoxy- aceticink(--~NHz acid--.- ..
hexane)-o-z- z CH3 CHz-CH(-CHz- CH3 phenoxy-aceticm-C(=NH)NHz acid hexane)-- z- 2 3 2- r 3- -p epoxy-aceticm-hexane)- acid o-z- z s z-CH(-CHz- Bn-O-phenoxy m-(:(=NH)NHz acetic acid hexane)-o-z- z -CHj -CHz-CH(-CHz- enoxyacehc aci m- z -hexane)-o-z- z CHj CHz-CH(-CHz- -p enoxyacehc m- z aci hexane)-o-SOz-NHz CH3 CHz-CH(-CHz- r'-phenoxyacehc m- z acid hexane)-o-z- z 3 CHz-CH(-CHZ CH3-phenoxy-aceticm-C(=U)NHz acid hexane)-o-z- z CH3 CHz-CH(-CHz- CH3-U-phenoxy m- z acetic hexane)- acid o-z- z CH3 CHz-CH(-CHz- Bn-U-phenoxy m- z acetic acid hexane)-o-~uz-Ntiz ~;t13 ~alz-Lnl-~alZ enoxye ano m- z hexane)-O-JVz-Nt12 lai3 l;riz-fall-l:riz--p eriOXy-a ano m-hexane)-o-JVz-Nriz ~;ri, Lnz-Lnl-~:n~ r-pnenoxy- emanoim-~l=ivn)ivnz hexane)-o-z- z s z z- 3-p epoxy-a ano m- z hexane)-O-JUz-Nri2 Lti, cay-~nl-~nz- ~n3-~-pnenoxy-emanoim-~l=ivn)ivnz hexane)-O-~uz-NHz , z z- n- -p epoxy a m- z ano hexane)-o-~u2 Hz cal3 r z- enoxye ano m- z N
hexane)-O-JVz Hz C;tl3 1:ri2-l:ril-l:riz-l;1-pnenOXyeiilan0lm-l;l=V)iVriz N
hexane)-o-~Vz Hz Ltl3 Lttz-l:tllWaiz-r-pnenoxy-etnanolm- z N
hexane)-o-JVz-lVriz ~n3 ~nz-~nl-~rir 3-p epoxy-a ano m-hexane)-O-JVZ nz Lti3 ~ttz-urll-~nz- aria-~-Pnenoxy- m-~l=v)ivnz w emanoi hexane)-o-~uz-Ntiz Lti3 ~nz-~nl-~nz tsn-u-pnenoxy- m-~l=u)mn2 emanoi hexane)-o-JUz-Nriz ~ti3 ~nz-unl-~n2- iviemyi pnenoxy-emyim-~l=rVn)wnZ
hexane)- ether o-~uz-wtiz cai3 ~nz-unlw;nz-nnemym-pnenoxyemym-hexane)- ether O-JU2-NHz cai3 c:n2-~nl-~ti2-enemy r-pnenoxy-emyim-hexane)- ether O-JUz t12 l;tl3 z' y- a Y 3-p epoxy- m- z hexane)- ethyl ether o-~uz-Ntiz Lti, z- z- a y 3- -p epoxy-m- z hexane)- ethyl ether o-JUZ-iVriz Lri3 Lri2-Lril-L'ri2-Memyi rsn-v-pnenoxym-~;l=ivn)ivnz hexane)- ethyl ether o-5Uz-Ntl2 l;Hj lalz-~:ril-laiz-enemy rnenoxyemyim-~;l=V)ivnz hexane)- ether O-JUz-Ntl2 Ltij ~:nz-Lnl-Lnz- a y -p enoxye m- z y hexane)- ether o-z- z s z- z- a n-C(=O)I~Z
y ,-phenoxyey hexane)- ether o-~uz-Nriz lal3 lalz lal(-lalz-lvieulyl m- z l:ri3-hexane)- phenoxyethyl ether o-~u~ tiz cal, lalz-lal(-lalz-l viemyl l:rij-u-m-~(=v)Nrlz N
hexane)- phenoxyethyl ether o-JVZ t12 C;tl3 lily-l;ti(-laiZ- Mettlyl tSn-v- m-N
hexane)- phenoxyethyl ether o-JUZ-Ntiz Cai3 l:Hi-l.al(-1x12-pneriyl m-(HO-phenyl))-.
O-5Vi-NHz 1x13 1x12-l;tl(-laiz_-p m-eny (HO-phenyl))-o-~VZ tlz 1a13 calz c:tl(-l:riz_-p m- z N eny (HO-phenyl))-O-JUZ-Nt12 1a13 calz-c:rl(-~riz-l:rl3-phenyl m- z (HO-phenyl))-O-JUZ-Ntiz 1;ri3 1;t12-C:ri(-l;riz-3 m--p eriy (HO-phenyl))-O-~Uz-Nriz lal3 l:rlz-l:rl(-l:rlz-rsn-V-phenyl m- z (HO-phenyl))-o-~u2 tiz 1a1, calz cal(-l:rlz-phenyl m- z N
(HO-phenyl))-O-~Uz-Nriz 1a1, l:riz-l:rl(-l:rlz-la-phenyl m- z (HO-phenyl))-O-JVZ-Ntlz 1;t13 Calz-Cal(-lainr-phenyl m-l:(=U)Nrl2 (HO-phenyl))-O-JVZ-Nt12 1.;ri3 1x12-lai(-1:112-1.:ri3-phenyl m-(HO-phenyl))-O-JU2-Nriz 1;ri3 l;tl2-lai(-l.;riy-3- m--p eriy (HO-phenyl))-O-~Uz-Nriz lai3 z z- n- m- z -p eny (HO-phenyl))-o-5Vz-Nriz llH3 z 2- m p-me (HO-phenyl))-o-JUz-Nriz t_;ri3 lalz-lal(-c:rizl:l-amlme p-~(=lvrl)mrlz (HO-phenyl))-o-5U2-Nriz (a13 Z- 2- -am p-me (HO-phenyl))-O-JVZ-NHZ laij lily-Cai(-1x12-1x13-anllllle p-l,(=lVti)lVrlz (HO-phenyl))-O-JU2-Nriz 1x13 l:riz-l;ri(-l:riZ-3_ p-_aril me (HO-phenyl))-o-~u2 HZ lai3 laiz-l;ri(-l;riZ-n_ p-N -aril me (HO-phenyl))-O-JUz-NtiZ 1x13 l:riy-11-1(-1x12-Arillme p- y (HO-phenyl))-O-JUZ-NH2 1;t13 lily-lal(-1x12-(:l-amlme p-l;(=U)Nrl2 (HO-phenyl))-O-JUZ-Nri2 1:113 lily-l:rl(-l:rlZ-r-anllme p-l:(=V)1Vr12 (HO-phenyl))-o-~uz-Nrlz l:ri3 l:rlz-l:ry-l;riz-l:ri3-anllme p-1.(=u)l~nz (HO-phenyl))-O-JU2-Nt12 lalj l:tlZ Cal(-l.;riZ-l:rig-v-arillllle p-l:(=U)lVtiz (HO-phenyl))-O-JUz t12 laig lily-l;ri(-1:ri2-liri-u-anllllle p-L(=V)lVriz N
(HO-phenyl))-o-~urNttz lai, ~nr~-Hl-~-nz-rnenyl-amino-carooxync m-1:(=l~ri)l~riz (HO-phenyl))-acid o-~Uz-Ntlz l:rij laiz-l:rl(-l:tlzeny m- z -ammo (HO-phenyl))-carboxylic acid o-~uz-Ntiz 3 z- z- -p m- z eny -ammo (HO-phenyl))-carboxylic acid = 160 -o- z- z s z- z- 3-p m-eny -ammo ,...
..
(HO-phenyl))-carboxylic acid o-5Vz-NHz C:H3 (:Hz-LH(-(:Hz-C:H3-V-pnenyl m-tr(=lvrl)lvriz ammo (HO-phenyl))-carboxylic acid o-SUB NHz CH3 C:Hz-C:H(-C;Hz-tin-U-phenyl m-L(=NH)NHz ammo (HO-phenyl))-carboxylic acid o-5Uz NHz C:H3 l:Hrl;H(-l:Hz-Ynenyl-ammo m-l:(=u)lvrlz caruoxync (HO-phenyl))-acid O-JUZ-NHZ 1:H3 I:HZ-l;ri(-l:Hz-l;l-prienyl-ammo m-(HO-phenyl))-carboxylic acid O-SUZ-NHZ (:H3 l:Hz-C;H(-l;Hzr-prieriyl-ammo m- . z (HO-phenyl))-carboxylic acid o-5Uz-NHz t;H, LHz-c:H(-LHi~ri3-pnenyi-ammo m- z (HO-phenyl))-carboxylic acid o-SUZ NHz C:H3 Ltlz-LH(-Ltiz-LH3-u-pnenyl-ammo m- z (HO-phenyl))-carboxylic acid o-5Uz NHz C:H3 l;tlz-C:H(-l:Hzn- m--p eny -ammo (HO-phenyl))-carboxylic acid o- z- z CH3 CHi CH(-CHz-a m- z y p epoxy-acetic (HO-phenyl))-acid ester o- r z 3 CHz-CH(-CHz-a m- z y -p enoxyacehc (HO-phenyl))-acid ester o- z- z z- z- a m- z ~,~. y s -p epoxy-acetic (HO-phenyl))-acid ester o-5U2-NHZ c:H3 MHz LH(-~riz-enemy m-~~=mri)mriz ~ri3-pnenoxy-(HO-phenyl))-acetic acid ester o-SUZ-NHZ (a13 1:H2-C;H(-laiZ-MemyW m- z a1,-u-pnenoxy-(HO-phenyl))-acetic acid ester O-5V2-NHZ c:H3 LHz-Lti(-LHz-Memyi m-~(=wri)rrriz tsn-u-pnenoxy (HO-phenyl))-acetic acid ester o- z- z - CFI3 CHz CH(-CHz-Methyl m- z Yhenoxyacetic (HO-phenyl))-acid ester o- O~ N~ CH3 CHz-CH(-CHz-Methyl m- z Cl-phenoxyacehc (HO-phenyl))-acid ester o- Oz-NHz CH3 CHz-CH(-CHz-Methyl m- z J'-phenoxyaceric (HO-phenyl))-acid ester o-5Vz-NHz c:H3 LHz-LH(-~HZ-nnetnyi m- z ~rij-pnenoxy-(HO-phenyl))-acetic acid ester o-5UZ NHz LH, LHz-Lti(-LHz-Metnyi m- z ~ri3-v-pnenoxy (HO-phenyl))-acetic acid ester o-5uz-NHz c:H3 LHzw:Hl-~nz-enemy m-~~=v)mriz tsn-u-pnenoxy (HO-phenyl))-acetic acid ester o- z- z - CH3 CHz CH(-CHz-Yhenoxyacehc m- z acid (HO-phenyl))-o- Z z - CH3 CHz-CH(-CHz--p m- z epoxy-acetic aci (HO-phenyl))-o- Z z - CH, CHz-CH(-CHz--p m- z epoxy-acetic aci (HO-phenyl))-o- z- z ~-- CHz-CH(-CHz-3-p m- z epoxy-acetic aci (HO-phenyl))-o-SOz-NHz CH3 CHz-CH(-CHz-CH3-U-phenoxy-acetic m-C(=NH)NHz (HO-phenyl))-acid o-SOz-NHz CH3 CHz-CH(-CHz-13n-U-phenoxy m- z acetic acid (HO-phenyl))-o-SOZ NFIz CH3 CHz-CH(-CHz-Yhenoxyacehc m-C(=U)NHz acid (HO-phenyl))-o-SOz-NHz CH3 CHz-CH(-CHz-Cl-phenoxyacehc m-C(=U)NHz acid (HO-phenyl))-o-SOz-NHz CH3 CHz-CH(-CHz-F-phenoxyacehc m-C(=U)NHz acid (HO-phenyl))-o-SOZ NHz CH3 CHz-CH(-CHz-CH3-phenoxy-acetic m-(:(=U)NHz acid (HO-phenyl))-o-z- z 3 z- z- 3- m-C;(=U)NHz -p epoxy acetic (HO-phenyl))-acid o-50z-NFIz CH3 CHZ CH(-CHz-Bn-U-phenoxy m-C:(=U)NHz acetic acid (HO-phenyl))-O-JUz-NHZ cal3 ~:rlz-~ril-~riz-enoxye m- z ano (HO-phenyl))-O-~Vz-Nriz lal3 c:Hz-fall-lalz-l:l-pnenoxy-emanol m- z (HO-phenyl))-o-~Vz-Nriz lal3 call-call-l;tlz-r-pnenoxy- m-l:l=lvrl)wrlz emanol (HO-phenyl))-O-JVZ-NH2 cal3 lalz-fall-Ltlz-l:rl3-pnenoxy-emanol m-l:l=lvrl)wrlz (HO-phenyl))-o-JUz rlz lal3 l:rlz-fall-~;rizl:rl3-v-pnenoxy-emanoi m-t;l=lrrl)ivrlz iv (HO-phenyl))-O-JVZ-Nri2 c~ri3 lalz-lall-l;tlz-tsn-V-pnenoxy m-~;l=lvrl)wrlz emanol (HO-phenyl))-O-JUZ-NHZ cal3 ~riz-~ril-~riz-rnenoxyemanol m-~l=u)wrlz (HO-phenyl))-o-~uz-Nriz l:rl3 l:rlz-l:rll-l:rlz-l:l-pnenoxyemanoi m-l:l=u)mrlz (HO-phenyl))-o-auz-NHz lal3 l:rlz-l:rll-l:rlz-r-pnenoxy-emanol m- z .
(HO-phenyl))-o-JVZ Hz lal3 lalz-call-l:rlz-~ri3-pnenoxy-emanol m-l:l=v)lrrlz N
(HO-phenyl))-O-JVz H2 C:ri3 lalz-lall-l;tlzj- m-N -p epoxy-a ano (HO-phenyl))-o-5VZ-Nriz , z Z- n- m- z -p epoxy-a ano (HO-phenyl))-o-JUZ-Nriz cal3 l;tlz Ltll-calz-ivleulyi m-l.l=ivrl)ivrlz pnenoxy-emyl (HO-phenyl))-ether O-JUZ-Nri2 c:H3 lalz Ltll-calz-ivleulyi m- z l:l-pnenoxyemyi (HO-phenyl))-ether O-JUZ-NH2 cal3 ~riz-~nl-~nz-ivlernyl m- z r-pnenoxy-emyi (HO-phenyl))-ether O-JUZ-NHZ cal3 lalz-fall-lalz-lvlemyl m- z ~ri3-pnenoxy-(HO-phenyl))-ethyl ether o-JUZ-Nriz cal3 lalz-fall-lalz-tvlemyllal3-v-pnenoxy- m-l:l=lvrl)ivrlz (HO-phenyl))-ethyl ether o-z z a i r a m- z y n--p epoxy (HO-phenyl))-ethyl ether o-~u2 Hz Cal3 latz-l:rll-l:rlz-Memyl m-t,l=u)lvtlz N rnenoxyemyl (HO-phenyl))-ether o-~uz-Ntlz cal3 ~riz-~ril-~rizivlemyll:l-pnenoxyemyl m-l:l=V)mrlz (HO-phenyl))-ether o-~uz-Ntlz cal3 ~riz-~ry-~nz-ivleulyl m-l.;l=u)mrlz r-pnenoxyemyl (HO-phenyl))-ether o-~uz-NHZ Cal3 lahlail-lirlz-Mettlyll:rlj- m-(HO-phenyl))- phenoxyethyl ether O-JUZ-NHZ 1:ri3 1;ri2-fail-lily- MeLllyll;rij-V-m-(HO-phenyl))- phenoxyethyl ether O-JUz-Ntlz cal, lalz-l:rll-l:rlz- a y n- m- z (HO-phenyl))-phenoxyethyl ether O-JUZ-1Vt12 lal3 z- z- P m- z enY
(Cl-phenyl))-o-JUz-NHz Cal3 z- 2- -p m- z eny (Cl-phenyl))-o-~uz-Ntiz cal3 l:rlz-l:rll-l:rlz-r-pnenyl m-l.l=wrl)mrlz (Cl-phenyl))-O-JVZ-NHZ 1:ri3 laiz-fall-lal2-l:rl3-prienyl m-(Cl-phenyl))-O-JUz-lVHz 1x13 l:riz-fall-lal2-1:ri3-u-prieriyl m-(Cl-phenyl))-= 162 -o- z- z s z- r n_ m--p enyl (Cl-phenyl))-o-~uz Nnz ~n3 ~nz-~nl-~nz-pnenyl m- z (Cl-phenyl))-o-~uz-Nnz , ~nz-c:nl-~nz_-p m- z eny (Cl-phenyl))-o-~uz Nri2 3 Y z- -p m- z eny (Cl-phenyl))-O-JVZ-Nriz 1x13 z- r 3-p m- z eny (Cl-phenyl))-o-~uz-Ntiz 1x13 Y z- 3- m- . z -p eny (Cl-phenyl))-O-JUz Nnz s z- r n- m- z -p eny (Cl-phenyl))-o-auz-Ntiz Lti3 Lnz-Lnl-Lnz-amime p-~l=mnyvnz (Cl-phenyl))-o-~uz Ntiz ~n3 ~nz-~nl-~nz-m-amime p-~l=mn~Nnz (Cl-phenyl))-O-JUZ-Nriy ~;n3 ~:nz-~:nl-tJnz-r-amime p-~.l=ivnyvnz (Cl-phenyl))-O-JUZ-Nri2 l;rlj 1:r12-l;rll-l;tlZ-~n3-amime p-~,l=ivnyvnz (Cl-phenyl))-O-JUZ-Ntl2 ~t~3 uti2 ~til-~nz-~n3 p-~l=Nn~Nnz u-amime (Cl-phenyl))-O-JUz-Nriz ~n3 ~nz-~nl-~riznn-u-amime p- z (Cl-phenyl))-o-~uz Ntiz ~:n3 ~;ttz-~nl-Lnz-amime p- z (Cl-phenyl))-o-JU2-Nri2 1:ri3 Y z- -ant p-me (Cl-phenyl))-o-JUz-Nriz uti3 unz-~nl-~nz-r-amime p-~l=v~Nnz (Cl-phenyl))-O-JU2-Ntl2 s i Y 3-am p- z me (Cl-phenyl))-o-JUz-Nriz ~;n3 ~:nz-Lnl-~:nz-~n3-u-amime p-t,l=vyvnz (Cl-phenyl))-O-JU2-Nri2 Ln3 utiz-~nl-~tiz-nn-u-amime p- z (Cl-phenyl))-o-5uz-Ntiz ~ai3 ~ai2 Ltil-t;tiz-rneny-ammo-carooxync m- z (Cl-phenyl))-acid o-JU2-Nti2 1:ri3 1x12-fall-1;ri2-l~1-rrieriyl-ammo m-(Cl-phenyl))-carboxylic acid o-~uz-Nnz ~:n3 ~:nz-~nl-~;nz-r-pnenyi-ammo m-~l=ivnyvnz (Cl-phenyl))-carboxylic acid o-auz-Ntiz ~:n3 ~:nz-~ry-~nz-~;n3 m-~l=mnyvnz pneny-ammo (Cl-phenyl))-carboxylic acid o-~uz Ntiz Lti, ~nz-~nl-~nz-~n3 m-~l=Nn~Nnz u-pnenyi ammo (Cl-phenyl))-carboxylic acid o-~uz-Ntiz ~:n3 ~;nz-~-nlw;nz-tsn-u-pneny m-~l=mnyvnz ammo (Cl-phenyl))-carboxylic acid O-JUZ-Nri2 cai3 ~riz-~nl-~tiz-rneny-ammo m-~l=u~Nnz carnoxync (Cl-phenyl))-acid o-~uz-Ntiz c:n3 ~:nz ~;nl-~nz-~a-pnenyi-ammo m-~l=u~Nnz (Cl-phenyl))-carboxylic acid O-JVy-NriZ c:n3 ~tiz-aril-~nz-r-pnenyi-ammo m- z (Cl-phenyl))-carboxylic acid o- z- 2 3 2 2- 3 m- z P
enY
-~o (Cl-phenyl))-carboxylic acid o-JUZ-Ntl2 cai3 c.;tiz-Lnl-Lnz-Lrl3 m-~;l=uyvnz u-pnenyi-ammo (Cl-phenyl))-carboxylic acid o-~uz-Ntiz s z- z- n- m- z -p eny -ammo (Cl-phenyl))-carboxylic acid o- z- z s z- z- a y p epoxy-aceticm- z (Cl-phenyl))-acid ester o- Z z CH3 CHz-CH~CHZ-Methyl Cl-phenoxyacehcm-(:(=NH)NHz (Cl-phenyl))-acid ester o- z- z CH3 CHz-CH(-CHz-Methyl F-phenoxy-m-C(=NH)NHz acetic (Cl-phenyl))-acid ester o-JU2-NHz ~:H3 ~atz-~:H(-LHz-nnetnym;ti3-pnenoxy-m- z (Cl-phenyl))-acetic acid ester o-5Uz-NHz LH3 t,ttz-~:H(-~;Hz-a Y 3- -P epoxy-m- z (Cl-phenyl))-acetic acid ester O-~Vz-NHz c:H~ MHz-pry-~riz-nnemyi rsn-u-pnenoxym- z (Cl-phenyl))-acetic acid ester CH3 2- z- a y enoxyacehc m- z o- z- 2 (Cl-phenyl))-acid ester o- z- z ~s CHrCH(-CHz-Methyl Cl-phenoxyacehcm-C;(=U)NHz (Cl-phenyl))-acid ester o- z- z - CH3 CHz-CH(-CHz-Methyl r'-phenoxyacehcm- z -(Cl-phenyl))-acid ester o-5U2-NHz C:H3 C;HZ-(:H(-tlHz-a Y 3-p epoxy- m-(Cl-phenyl))-acetic acid ester O-5U2-NHZ 1;H3 C:H2-(:H(-~;Hz-a Y 3- -p epoxy m-(Cl-phenyl))-acetic acid ester o-5Uz-NHz C:H3 caiz-Lti(-LHz-lvlemyl tan-U-pnenoxym-~l=v~wriz (Cl-phenyl))-acetic acid ester o- z- z CH3 CHz CH(-CHz-Yhenoxyacehc m- z acid (Cl-phenyl))-o- Oz-I~HZ CHj CHz-CH(-CHz--p epoxy-acetic m- z aci (Cl-phenyl))-o- z- z CH3 CHz-CH(-CHz-r'-phenoxy- aceticm- z acid (Cl-phenyl))-o- z z CH3 CHz-CH(-CHZCH3-phenoxy-aceticm-C(=NH)NHz acid (Cl-phenyl))-o- z-NHz CH3 CHz-CH(-CHz-CH3-U-phenoxy-aceticm- z (Cl-phenyl))-acid o- z- 2 CH3 CHz-CH(-CHz-n- -p epoxy aceticm- z aci (Cl-phenyl))-o- z- Z ZH3 CHZ CH(-CHz-Phenoxyacehc m- z acid (Cl-phenyl))-o-SOz-NHz CH3 CHz-CH(-CHz-Cl-phenoxyacehc m-c.;(=U)NHz acid (Cl-phenyl))-o-SOz-NHz CH3 z z- -p enoxyacehc m- z aci (Cl-phenyl))-o- z- z ~s z- z- 3-p epoxy-aceticm- z aci (Cl-phenyl))-o- z- z 3 z- z- 3- -p epoxy aceticm- z (Cl-phenyl))-acid o- z- z s CHz CH(-CHz-Bn-U-phenoxy m-C;(=U)NHz acetic acid (Cl-phenyl))-o-SUz-NHz C;H3 I:HZ c:H(-c:Hz-enoxye ano m- z (Cl-phenyl))-o-5uz-NHz c:H3 LHZ ~Hl-~tiz-~i-pnenoxy-emanoim-~l=mnyvriz (Cl-phenyl))-o-SUz-NHz C:H3 LHz-~Hl-c:Hz-r-pnenoxy- emanoim- z (Cl-phenyl))-o-JUZ-NHz C:H3 l:Hz-l;H(-1;H2-1;ri3-pnenoxy-emanoim-~:~=mriJmriz (Cl-phenyl))-O-JVZ-NHZ C:H3 1:H2-l;H(-l:Hz~ri3-u-pnenoxy-emanoim-~~=mryvriz (Cl-phenyl))-O-JUZ-NH2 (a13 1:H2-l:H(-1:ri2-~sn-u-pnenoxy m- z emanoi (Cl-phenyl))-o-~Uz-NHz C:H3 t;tiz-c_:H(-LHZ-enoxye ano m- z (Cl-phenyl))-= 164 -z- z s z- z- Cl-phenoxyethanol m-C(=U)NHz m o-(Cl-phenyl))-o-5Vz-Nriz LH3 LHz-t;Hl-LHz-r-pnenoxy-eulanoi m-~l=u)r~riz (Cl-phenyl))-o-JU2-NHz 1;H3 1:H2-C;H(-C:HZ-LH3-pnenoxy-emanol m-~l=~Jr~riz (Cl-phenyl))-o-~Uz-NHz c:H3 LHz-LHl-LH2LH3-u-pnenoxy- m- z emanol (Cl-phenyl))-o-~UZ Hz ~:H3 c:Hz-~:Hl-~:HZtsn-u-pnenoxy- m-~l=u)lrriz N emanol (Cl-phenyl))-o-JVZ-Nri2 LH3 c:Hz LHl-c:Hz-lviemyl m-~l=r~ri)r~riz pnenoxy-emyl (Cl-phenyl))-ether o-JUz-NHz ~:H, LHz ~;tll-Ltiz-lvlemym;l-pnenoxyetnyl m-~:~=lrri)lvriz (Cl-phenyl))-ether O-JUZ-NHz ~;H, c:Hz tail-Ltiz-1\netnyl m- z r-pnenoxy-emyl (Cl-phenyl))-ether o-~uz-NHz LH3 c:Hz-t_;Hl-MHz-nnetnyl m- z ~ri3-pnenoxy-(Cl-phenyl))-ethyl ether o-~u2 Hz l:Hg C:riz-l;tll-lalz-MeLllyl m-N 1:ri3-V-pnenOXy-(Cl-phenyl))-ethyl ether o-SUz-NHz c:H3 c:Hz-c:Hl-~:Hz-a m- z y n--p enoxy (Cl-phenyl))-ethyl ether o-5Uz-NHz LHj z z- a m- z y enoxye y (Cl-phenyl))-ether o-~Uz-Nriz ~:H, ~;Hz tail-Ltiz-Metnym;i-pnenoxyemyl m-~:~=u)r~riz (Cl-phenyl))-ether o-5Uz-NHz C:H~ (:HZ-t.Hl-(:HZ-a m- z y -p enoxye y (Cl-phenyl))-ether o-JUZ-NHZ 1;H3 l;Hz-l;Hl-l;riz-a m- z Y
a-(Cl-phenyl))- phenoxyethyl ether o-JUZ-NHz 1;H3 1;H2-l;Hl-C;tiz-i vletnyl Sri,-u-m-(Cl-phenyl))- phenoxyethyl ether o-~Vz-NHz uH, c:Hz-uHl-c:HZ- Memyl tsn-u- m-~l=u)wriz (Cl-phenyl))-phenoxyethyl ether O-JU2-Nriz c:H3 LHz-~Hl-MHz-phenyl m-~l=r~ri)r~tiz ~z)-O-JUz-NHz 1;H3 (:HZ-l;Hl-C;HZ-l:l-prienyl m- z ~z)-o-~uz HZ 1:H3 1:H2-l;Hl-l;Hz-r-prieriyl m-l:l=1Vri)1Vr12 N
~z)-O-~UZ-NHZ C:Hj (.;H~ t.Hl-LrlZ-j-p m-eny ~z)-O-JUZ-NHZ C:Hj l:Hz l;Hl-lain-3- m- z -p eny NHz)_ O-JVZ-NHz C;H3 l:Hz-l;Hl-1;H2-tfn-U-phenyl m-NHz)-O-JUZ-lVtiz 3 2- r P m- z enY
~z)-o-z- z s r r -p m- =O)NHz eny ~z)-z- 2 3 2 2' -p m- z eny ~2)-O-5Uy-NH2 1;H3 l:H2l:Hl-1;H2-3-p m-eriy NHz)_ o-5u2 Hz s z- z- 3- m- z N -p eny ~z)-o-Oz-NHz CH3 z- z- n- m- z -p eny NHz)-O-JUZ-NHZ 1;H3 l:Hz-l:Hl-l;Hz-11I1e p-~2)-O-JUz t12 1;ri3 l;rii l;tll-~riz_-am p- z 1V me ~2)-o-z- 2 3 2- z- -am p-me ~z)-O-SUz-NHZ lal3 l;Hz-l:H(-l:Hz-3-ant p-me ~z)-o-SUz-NHz s z- r 3- p- z -am me NHz)_ o-5U2-NHZ C:H3 1;H2-C;H(-C:HZ-n_ p--am me ~z)_ o-z- z s z- z- i p-C(=O)NHZ
me ~z)-o-z- z s z- z- -atli p-C(=O)N
me ~z)-o-5Uz-NH2 1;H3 C:HZ-l;H(-l:Hz -ant p-me ~z)-o-5Uz-NHz C:H3 C:Hz-1:H(-I~HZ 3-am p- z me NHz)_ 2- 2 3 2- 2- 3- p-l.(=V)1Vr12 -~1 me NHz)_ o-5UZ-NHZ C:H3 l;Hz l:Hz-tSn-u-arillme p-l;ti(-~z)-o-~uz-NHz cal3 c:Hz-t_;H(-l:Hz-eny m- z -ammo-car oxy is NHz)- acid o-5V2 HZ 1;H3 lalz-lal(-1x12-l;l-Ynenyl-ammo m-N
NHz)- carboxylic acid O-5UZ-NHZ 1x13 1;H2-l:H(-l;Hz-r-pnenyl-ammo m-NHz)- carboxylic acid o-~uz Hz 1x13 l;Hz-1:H(-l:Hz-1x13-pnenyi-ammo m- z N
NHz)- carboxylic acid o-~Uz Hz 1:H3 c:Hz lalz-3_ m- z N 1:H(- _p eny ammo NHz)- carboxylic acid o-JUZ-NHZ 1;H3 C;tl2-C:H(-t;H2-n- m- z -p eny ammo NHz)- carboxylic acid o-5V2-NH2 1x13 1:H2-l:H(-l;tlZ-Yrienyl-ammo m-CarDOXyIIC
NHz)- acid o-5uZ-NHZ 1x13 1:H2-l;H(-l:rlz_-p y -ammo m- z en NHz)- carboxylic acid o-5uz-NHz 1x13 l:Hz l;tlz-r-pnenyi-ammo m- z 1:H(-NHz)- carboxylic acid O-JUz-NHZ 1:H3 l;tlz 1;H2-1;H3-prieriyl-ammo m-l:(=U)1Vr12 ljH(-NHz)- carboxylic acid o-JUZ-NHZ l;ti3 l.:Hz-l;H(-1:H2-1x13-u-prienyl-ammo m-l.;(=V)1Vr12 NHz)- carboxylic acid o-~uz-NHz 1x13 lalz-lal(-l;tlz-tsn-u-pnenyi-ammo m- z NHz)- carboxylic acid o--SO~lHz CH3 CHz-CH(-CHz- Methyl m-C(=NH)NHz phenoxy-acetic NHz)- acid ester ~ OZ Hz CH3 CHz-CH(-CHz- Methyl m- z N Cl-phenoxyacehc NHz)- acid ester o-r z-- s CHz-CH(-CHz- Methyl m- z r'-phenoxy-acetic NHz)- acid ester o-5uz-NHz 1:H3 1:H~ l:Hz-ivlemyi m-1:(=~ri)wriz 1;H(- l:rl3-pnenoxy-NHz)- acetic acid ester O-JUZ-Nri2 l:Hg (:Hz-lal(-l:riZ-a m-Y
s' -P
enOXy-NHz)- acetic acid ester o-~uz-NHz 1:H3 z- z- a m- z y n--p enoxy NHz)- acetic acid ester z- z s z- z- a Y ,_,~ ~.,,...
enoxyacehc m-NHz)- acid ester o-z- z s z- z- a m- z Y
-p enoxyacehc NHz)- acid ester c-r z s z- z- a m- )NHz y -p enoxyacehc NHz)- acid ester o-2 2 3 2- z- a Y s-P epoxy- m-t_:~=~~~riz NHz)- acetic acid ester o-z- 2 3 2- z- m~(=O)NHz 11 u1 m.aa v a Y 3 -P epoxy NHz)- acetic acid ester o'z- 2 3 2- r a y n- -p epoxy m- (-O)~z NHz)- acetic acid ester o-z- z s z- z- enoxyacehc aci m- (=~H2 NHz)_ -o-z- 2 3 2- z- -p epoxy-acetic m- (=NHjl~Hz aci ~z)-o-z- z s r z- -P epoxy- aceticm- z aci ~z)-o-r z s z- z- ,-p epoxy-aceticm- z aci ~z)-o-z- z z- z- ,- -p epoxy-aceticm- z ~,~1 s NHz)- acid - -o-z- z s z- z- n~(=RH)NHz n- -p epoxy acetic acmT
~z) o-z- z a r z- enoxyacehc aci m- 2 ~2)-o-z- z 3 CHz CHz- -p enoxyacehc m- z CH(- aci ~z)-o-z- z CH3 CHz-CH(-CHz- r~-phenoxyacehc m- z acid NHz)_ o-z- z 3 CHZ CHz- CH3 phenoxy-aceticm- z CH(- acid NHz)_ o-z z CH3 CHz-CH(-CHz- CH3-U-phenoxy m- z acetic NHz)- acid o-z- z CH3 CHz-CH(-CHz 13n-U-phenoxy m- z acetic acid ~2)-o-5Uz-NHz CH3 t;Hz-c:Hl-LHz- rnenoxyemanoi m- z NHz)_ o-5Uz-NHz C;H3 LHz Lttz--p epoxy-a ano m- z LHl-~z)_ o-z- z s z z- -p epoxy- a ano m- z ~z)-o-5Uz-NHz C:H3 ~ r 3 p epoxy-a ano m- z ~z)-o-SUz-NHz C:H3 i z- 3- -p epoxy-a m- z ano ~z)-o-r z 3 z- z- n- -p epoxy a m- (=NH)NHz ano ~z)-o-SUz-NHz C:H3 z- z- enoxye ano m- z ~z)-o-z- z 3 z- z- -p enoxye ano m- =O)NHz NHz)_ o-5Uz-NHz C:H3 (:Hz LHz- r-pnenoxy-emanoim- z t_;Hl-NHz)_ o-z- z 3 z- z- 3-p epoxy-a ano m- z ~z)-o-JUZ Hz C:H3 c:Hz-fail-~:Hz-Lti3-u-pnenoxy- m- z N emanoi ~z)-o-5uz-NHZ LH3 e:Hz-LHl-MHz- tin-u-pnenoxy- m- z emanoi ~z)-o-z- z s r r a y p epoxy-a m- z y NHz)- ether o-z- z s z- z- a y -p enoxye m-y NHz)- ether o-z- z s z- z- a y -p epoxy-a m- z y NHz)- ether o-z- z 3 z- z ' P epoxy- m- NHZ
~
e ~ e z) ther Y
0-JVZ-NHz s z- z- et m-y -p enoxy-NHz)- ethyl - ether o-SOz-NHz CH3 CIA- z- a m- z Vlll -vlly n--p enoxy NHz)- ethyl - ether o-Saz-~ CH3 a m- z ull -ully vll~ z- enoxye z- y NHz)- ether o-SOz-NHz ~3 - z- z_ a m- z - y _p enoxye y NHz)- ether o-SOz-Nx2 C1~ - a m- z fill -vllY
Vlll r -p z- enoxye y NHz)- ether o-JVZ-lVriz 1;H3 1.;H2-l:H(-C:H2-Nlettlyl m-(.:(~)NH2 C;Hj-NHz)- phenoxyethyl ether O-JV2-1Vt12 1.;H3 (:HZ-l:H(-laiZ- Methyl C;H3-U- m-(:(~)NHz NHz)- phenoxyethyl ether o- wz-NHZ ~H3 ~Hz-~Hl-~Hz- Methyl tin-V- m-C(=V)NHz NHz)- phenoxyethyl ether Other preferred compounds of formula I, having the sub-formula Ib, are set forth in Table 76, below.
Table 76 Formula III
L
s R
o- z- z enyl m_y ~~z _ o- z- z z _p m-eny o_ z- z - -p m_C(-~~z enyl-z- 2 2 3- P m- z enY
o' z- z z 3- ~ p end Iri-~z o- z- z z n_ p m- z _ eny o- z- z 2 ehyl m-C~~)~z o- z- z z -p m_C~-0)~z eny o- z- z z -p m_ eny o' z- z z ,- p m=i -eny o- z- z z ~- - p eny m_ o z n_ eny m Z
z- z - _p o- z- z z i p-~:(=mtt~r~riz me o- z- z z a P- z o- z- z z -am P~~z the o- z- z z 3-am p- z the o- z- z z 3- P- z -~
a o- z- z z n- p-t,(=~tt~~tiz me o- z- z z a P' z o- z- z z me P- z o- z- z z -am p_ z me o- z- z z 3-am p_ z me o- z- z z ~- p_ z -am a o- z- z z n_ p-_a me z- z z eny m- z -ammo-car oxy c acid o- z- z z eny m- z -amino car oxy is aci o- z- z z -p m- z eny -ammo carboxylic acid o-~uz-wtiz r~ l,riz l:ri3-pnenyi-ammo m-t,(=Nti)Nriz carboxylic acid O-JVZ-Ntiz t~ laiz l:ri3-u-pnenyi m-1:(=Nti)Nriz ammo carboxylic acid o-~uz-Ntiz r~ l:riz rsn-u-pnenyi m- z ammo carboxylic acid o-JUZ-NtlZ ri Z eriy m--ammo car OXy 1c acid O-JVZ-NHZ H z -p m- z eny -ammo carboxylic acid O-~Uz-NHz ti talz r-phenyl-ammo m- z carboxylic acid o-~Uz-NHz W a1z ~ai3-phenyl-ammo m- z carboxylic acid o-JUz-NHZ H 1x12 lai3-u-pnenyi-ammo m-~(=u)rVriz carboxylic acid o-JUZ NHz ti laiz tsn-u-phenyl-ammo m-1J(=U)ivrtz carboxylic acid o-SU~lHz H C;Hz Methyl m-C;(=NH)NHz phenoxy-acehc acid ester o- Oz-NHz H (:Hz Methyl m-C;(=NH)NHz (:1-phenoxyacehc acid ester o- z- z - H CHz Methyl m- z - r'-phenoxy-acehc acid ester O-SUZ-NHZ H laiz Metnyi m- z l:ri3-pnenoxy-acetic acid ester o-SUZ-NHZ H 1:H2 MeTllyllal3-u-prieriOXy- m- y acetic acid ester o-SUz-NHz H LHz Merry m- z tsn-u-pnenoxy acetic acid ester o- Z z H - CHz Methyl m- z - Yhenoxyacehc .
acid ester o- z- z z - Methyl m-C;(=U)NHz C1-phenoxyacehc acid ester o- z- z 2- Methyl m- z F-phenoxyacehc acid ester o-SUz-NHz H c:Hz a m- z y 3-p epoxy-acetic acid ester O-SUZ-NHZ H c:Hz Memyi m- z l:rij-u-pnenoxy acetic acid ester o-SUZ-Nri2 H c:riz enemy m-1:(=u)mriz tsn-u-pnenoxy acetic acid ester o- z- z z enoxyacehc m- z aci o- z- z z -p m-epoxy-acehc aci o- r z z -p m-C;(=NH)NHz epoxy-acehc aci o- r z z 3- p epoxy-acehcm- z aci o- z- z z 3- m- z -p epoxy-acehc acid o- z- z z n- m- z -p -epoxy acehc aci o- r z z enoxyacehc m- NHz aci o- z- z z -p m-enoxyacehc aci o- r z z -p m-enoxyacehc -aci o- r z z 3-p m- NHz epoxy-acehc -aci o- z- z z 3- m- 2 -p epoxy acehc acid o- z- z z n- m- z -p epoxy acehc aci o- z- z z enoxye m- )NHz ano o- r z z -p m-epoxy-a ano o-2 z H z -p m-- epoxy=
ethanol -o-z- z H z 3-p m- z - epoxy-a ano o-z- z H z 3- p epoxy-etTianolm- z - -o-z- z H z n- epoxy a m- z - ---p ano o~z-~HZ H Cf ~ enoxyethanol m o-z- z H z -p m- z - - enoxyetfiano o-z- z H CIA F=pfienox~ol iris o-z- z z 3- p m- z . _ epoxy-a ano o-- ~2 ~3=a=p~enoXy-ethapolm-C'~
-o-- z ~ n_ epoxy- ethanolmZ'(=O)NF~
_p o-z- z z ethy m-C(=
p epoxy-et y ether o-~uz-Nriz ti ~riz nnemyi m-~(=Nri)Nriz m-pnenoxyemyi ether o-~uz-Ntiz z a m- z y -p epoxy-a y ether O-JUz-Nriz trtiz a m- z y 3-p epoxy-ethyl ether O-JUz-Ntiz ti trtiz. nnemym:ri3-u-pnenoxy- m- z ethyl ether O-JVz-Nriz m aiz nnemyi m- z tsn-u-pnenoxy ethyl ether o-JUz-Ntlz n l.;tlz MeTtlyl m- z YnenOXyelllyl ether O-~Uz-Nriz t m ;tiz Mewyma-pnenoxyemyi m-~,(=u)mnz ether o-5Vz-Nriz ti Ltiz Memyi m-~(=u)~riz r-pnenoxyemyi ether o-5Uz-NHz rt ~:riz nnetnymai3- m-~:(=u)Nriz phenoxyethyl ether o-JUz-Ntlz ti uriz memyi m-~,(=v)mriz ~ri3-u-phenoxyethylether o-JVz-Ntlz H lalz Melllyl m-L(=U)lVtlz tSn-U-phenoxyethyl ether o-z- z z- z P m- z enY
o-z- z z- z -P m-~-(=Nti)Ntiz enY
o-z z z- z -P m- z enY
z- z z- z a- P m- z enY
n-r z z- z 3- - p eny in~(=NH)NHz o-r z z- z n_ eny m- z _p o-z- z r z P m- )~z enY
o-z- z z- z -P m-~;(=u)mriz enY
o-r z z- z -P m- z enY
o-r z r z s- P m- z enY
o-z- z z- z ,- - p eny m- z o-z- z z- z n_ eny m- _ ~NHz _p o-z- z z- z m p- z me o-z- z z- z -am p- z me o-z- z z- z -am p- z me o-z- z z- z 3-am p-me z z z- z 3- p- z -am me o-z- z z- z n_ p-_~
me o-z- z z z m p- z me o-z- z z- z -am p- z me o-r z z- z -ani p- z ' me o-z- z z- z 3-am p- z me o-r z r z 3- p_ z -am -me o-z- z z- z n_ p- z _~
me o-r z z- z eny m- z -ammo-car oxy is acid o-z z z- z enY m- )~z -o car oxy is aci O-~Uz-NHz z- z -p m- z eny -ammo carboxylic acid O-lVZ-Ntiz h l;rlz-l:HZ uri3-pnenyi-ammo m-~:(=r~riJr~riz carboxylic acid O-JUz-NHz ri uriz-uriz ~ai3-u-pnenyi m-~:(=r~tiJNtiz ammo carboxylic acid o-~uz-Ntiz m ;tiz-~riz rsn-u-pnenyi m-~(=ivriJNriz ammo carboxylic acid o-~uz-Ntiz n uriz-~riz rnenyi-ammo m-~(=uJwriz carnoxync acid O-~uz-Ntiz ri uriz-~riz m-pnen yi-ammo m-~(=uJwriz carboxyl ic acid o-~uz-Nriz ri ~riz-~riz r-pnenyi-ammo m-~(=uJrrriz carboxylic acid o-~uz-Ntiz tm -rIZ-~-riz ~:r13-pnenyi-ammo m- z carboxylic acid o-~uz-Ntiz tm ;riz-taiz ~;ry-u-pnenyi-ammo m- z carboxylic acid O-aVz-NHz H l;riz-lalz tSn-V-prienyl-ammo m-carboxylic acid o- z- z - H z- z a m- z y p epoxy-acehc acid ester o- z- z z- z a m- z y -p enoxyacehc acid ester o- z- z z- z a m- z y -p epoxy-acehc acid ester o-5Uz-NHz H Ltlz-~ttz lviemyi m- z ~ri3 pnenoxy-acetic acid ester o-~Uz-NHz H C:Hz-l:Hz Metnyl m-t_;t13-u-pnenoxy-acetic acid ester o-5Uz-NHz H c:Hz-LHz Memyi m- z rsn-u-pnenoxy acetic acid ester o- z z CHz CHz Methyl m- z Yhenoxyacehc acid ester o- z- z H CHz CHz Methyl m- z C1-phenoxyacehc acid ester o- z- 2 H CHz-CHz Methyl m- z r'-phenoxyacehc acid ester o-SVz-Nri2 H ~:Hz-LHz Memym;tl3 m- z pnenoxy-acetic acid ester o-5Uz-NHz H c:H2 LHz Memyi m-~(=uJwriz Lti3-u-pnenoxy acetic acid ester O-5U2-NHz H 1;H2-(:Hz lVlelllyl m- z tiri-V-prierioxy acetic acid ester o- z- z z- z enoxyacehc m- z aci -o- z- z z- z -p m- 2 epoxy-acehc aci o- z- z z- z -p m-(:(=NH)NHz epoxy-acehc aci o- z- z z- z 3-p m- z epoxy-acehc aci o- 2 2 2 2 3- m- z -p epoxy-acehc acid o- z- z z- z n- m- z -p epoxy acehc aci o- z- z z- z enoxyacehc m ~~~)NHz aci o- z- z z- z -p m- z enoxyacehc aci o- z- z z- z -p m- z enoxyacehc aci o- z- z z z 3- p ri-C(=O)NHz epoxy-acehc acm o-S02-NHz H CHz-CHz CH3-U-phenoxy m- z acehc acid o- z- z z- z n- m- z -p epoxy acehc aci o- z- z z- z enoxye m- =NH)NHz o o- z- z z- z -p m- NHz epoxy-a ano o-z- z z- z -p m- z epoxy-ethano o-z- z r z 3_ p m- z epoxy=et ano o-z- z z- z LHa- u_pnenoxy-emanolm- rlz o-z- z z- z n- epoxy a m- z -p ano o-z- z z- z enoxyethano~ m o-z- z r z -p m- z enoxye -ano o-z- z z- z -p m-C(=O)NITz epoxy-ethanol o-z- z z- z ,-p m-C(=
epoxy-e~
o-z- z z- z 3- p epoxy- m- z - a ano -o-z- z z- z n- enoXy- e~ rim-C(=O) -p --o-z- z z- z a m-C(=NH)I~lFi2 yTp epoxy-et y ether o-~uz-lvrlz m ;riz-~riz lvleulyl m- z m-pnenoxyemyl ether O-JUZ-NriZ ti ~tiz-~tiz lvlemyl m-~l=lvrl)lvrlz r-pnenoxy-emyl ether O-JUz-lvtlz ri ~:rizriz enemy m-~~=lvrl)lvrlz ~ ~ri3-pnenoxy-ethyl ether o-~uz-Ntiz t m ;tiz-~riz enemy m- z ~ri3 u-pnenoxy-ethyl ether o-~uz-lvtlz ti ~riz-~riz lvlewyl m-~~=lvrl)lvrlz rsn-u-pnenoxy ethyl ether o-~Uz-Ntiz ti ~aiz-~aiz lvlemyl m-~:(=v)lvrlz rnenoxyemyl ether o-~uz-lvtiz t1 Ltlz-~aiz nnetnym;i-pnenoxyemyl m-t.~=v)lvrlz ether o-5uz-lvtiz t1 Ltlz-Ltlz lvlemyl m- z r-pnenoxyemyl ether o-JUZ-lVri2 H i z a m- z Y
phenoxyethylether O-JU2-NtiZ ti ~riz-~riz lvlemyl m- z Sri,-u-phenoxyethylether o-SUz-Nriz ti calz-Ltlz l vleulyl m-~~=U)lvrlz tsn-u-phenoxyethylether o-z- z r r z P m- z eriY
o-z- z z z-z -p m- z enY
o-z- z r r z -p m- ~z enY
o-r z z- z z a- p m- z enY
o-z- z z- z-2 3_ - p eny m-~:~=lvrl)lvrlz o-z- z z- z-Z ri_ eny m-_p o-z z r z-z p m=C(=~~z eny o-z- z z- z-z -p m- z enY
o-r z z- z-z _p m-eny o-z- z z- z-z 3 p m- ~z eriY
o-z- z z r z 3- _ p eny m_ (~z o-z- z z- z-z n_ eny m- z _p z- z r z-z lee p_ -o-z- z z- z-z -am p- z me o-z- z z_ z_z -am p- z me o-z- z z- z-z 3-am p- (=z me o-z- z z- z-z 3 p- z -am me o-z- z r r z n_ p- ~NIT)NHz _~llne o-r z r z'z m p- z lee o-z- z z- z-z -am p- z me o-z- z z- z-z -aril p_ 2 me o-i z r z-z 3-am p- ~ O)NHZ
me o-z- z z- z-z 3- p- z -and me o-z- z z- r z n_ p_ 2 _am me o-z- z z- z-z eny m- NFfz -amino-car oxy lc acid o-z- z z- z z eny m- z -alnlno car oxy is aci o-SOz-NHz H CHz-CHz-CH2 -p m enyl-amino carboxylic acid o-~u2 riz m :riz-~:riz-t,riz ~ri3-pnenyi-ammo m-~:~=NtyNtiz m carboxylic acid o-~u2 riz m ;riz-~:riz-t,tiz ~ri3-u-pnenyi m-t.~=NtyNtiz m ammo carboxylic acid o-~u2 riz n ~riz-~rizriz nn-u-pnenyi m-~~=NryNriz N ~ ammo carboxylic acid O-JUZ-Nriz z- r z eny m- z -ammo car oxy is acid o-z- z r z-z -p m- z eny -ammo carboxylic acid O-JU2-Nriz z- r z -p m- z eny -ammo carboxylic acid O-JVz tiz tm ;tiz-~:riz-~:riz ~ai3-pnenyi-ammo m- z N carboxylic acid o-JUz tiz H ~alz-Lttz-~alz 3- m- z N -p eny -ammo carboxylic acid O-JU2 HZ ti lalz ri2-l:riy tSn-u-pnenYi-amino m-N 1; carboxylic acid o-SOz~Hz H CHz-CHz-CHz Methyl m-C(=NH)NHz phenoxy-acetic acid ester o-SOz-NHz H CHz-CHz-CHz Methyl m-C:(=NH)NHz C:1-phenoxyacehc acid ester o-SOz-NHz H CHz-CHz-CHz Methyl m-(:(=NH)NHz >~~-phenoxy-acetic acid ester o-~u2 Hz H l;tiz-~atz-~alz lvletnym;tlj-pnenoxy- m-~:(=r~ri)rVriz N acetic acid ester O-JVZ-NHZ ti 1:H2-1;H2-1;H2 lVlelllYi m-l:~=lVt1)Ntlz l;tlg-u-pnenOXY-acetic acid ester o-~uz-NHz H ~tiz-~riz-~-tiz iviemyi m- z nn-u-pnenoxy acetic acid ester o-SOz-NHz H CHz HzHz Methyl m- z C C Yhenoxyacetic acid ester o-SOz-NHz H i Z z a m- z y -p enoxyacehc acid ester o-z- z - ~I CHz HZHz Methyl m- z C C F-phenoxyacetic acid ester o-~u2-NHz H ~aiz-~ay-cay a m- z y 3-p epoxy-acetic acid ester O-JUZ-NHz H Ltlz-LHz-c:Hz iviemyi m- z ~ri3-u-pnenoxy acetic acid ester o-JUZ-NHZ H C;H2-l:riz-1:ri2 lVlelllYi m-tSn-u-prieriOXY
acetic acid ester o-z- z z- z-z enoxyacehc m- z . aci o-z- z z- z-z -p iri-C(=NIT)NHz epoxy-acetic aci o-z z z r z -p m- z epoxy-acetic aci o-z- z z- z-z 3-p m-epoxy-acetic aci o-r z r r z s- m-C(=NH)NHz -p epoxy-acetic acid .
o-r z r z-z n- m- z -p epoxy acetic aci o-z z z- z-z enoxyacehc m-aci o-r z r z-z -p m- z enoxyacehc aci o-z- z r z-z -p m-(:(=U)NHz enoxyacehc aci o-z- z z- z-z 3- p epoxy-aceticm- z aci o-z- z z- z-z a- m--p epoxy acetic acid o-z- z z- z-z n- m- z -p epoxy acetic aci o-z- z z- z-z ~ m- NH NHz enoxye ano o-z- z z- z-z -p m- z epoxy-a ano o-r z z- z-z -p m- z - epoxy-a ano o-z- z g r z-z 3-p m- z epoxy-ethanol o-z z r r z 3- p epoxy-a m- z - ano o-z- z ~ z- z-z n- epoxy ethanem--p -o-z- z z- z-z enoxye m- z ano -o-z- z z- z-z -p m-enoxye anoI
_ o-z- z ~z- ~z-~z -phenoxy-ethanol m~O)IVHz o-z- z z- z-z 3- p m- z epoxy-a ano o-z- z ~C HZ=z 3- O-p~enox~anolm- z o-z- z CH2= z-z n- epoxy- ethanolm- (= z -p o-z- z z- z-z a m- z y p epoxy-a y ether o-~uz-wriz ti ~riz riz-~rizmemym;i-pnenoxyeuryi m-~.I=mryvriz ~;
ether O-JUz-lVri2 ti z- z-z a m- z y -p epoxy-a y ether o-SOz-NHz H CHz Hz-(:Hz ' m- z C; a y 3-p epoxy-ethyl ether O-5u2-NHZ ti z- z-z a m- z y -p epoxy-ethyl ether O-JUz-Nriz t-~ ~tiz-c:riz-~tizMemyi m- z rsn-u-pnenoxy ethyl ether O-JUZ-NHZ ri Ltiz-cai2rizMemyi m- z ~ rnenoxyemyi ether o-SOz-NHz H CHz-CHz-CHz et m- z y -p enoxye y ether o-~uz-Ntiz ti ~riz-~nz-~nz memYl m- z r-pnenoxyemyi ether O-JU2-Nri2 H caiz-~tiz-~tizMetnyi m-~I=u~wriz ~ri3-phenoxyethyl ether o-~uz-Ntiz t-~ ~tiz-~riz-~rizMemyi m-~l=uyvriz ~ri3-u-phenoxyethyl ether O-JUZ-1VH2 ti ~tiz-~riz-Ltizenemy m-~~=u~wriz ~n-u-phenoxyethylether o-z- z z- s P m- z - enY
o-z- z z- 3 -p m_ - eny o-z- z z- 3 -p m-~.~=mtiyvtiz - eny ~
o-r z z- s 3- P m- z - enY
-o-r z z- 3 3- - p enyI m-C(=NH)NHz -o-z- z z- 3 n- eny m- z - -p o-z- z z- 3 P m-_ enY
o-~u2 tiz z- , -p m-~t=u~wriz N - eny o-z- z z- 3 -p m-~~=uyvriz - eny o-z- z z- 3 a-P m-~-l=u)ivtiz - enY
o-z- z z 3 s- P eny m- (=O)NHz - - -o-z- z z- s n- enyl m-C(=O)NHz - -p o-r z z- j m p- z - me o-z- z z- 3 -am p- ~z - me o-z- z z- 3 -am p_ - me o-z- z z- s 3-am P_ z - me o-z- z z- s 3- p- NHZ
- -am me -o-z- z z- s n- P-C(-~)~z - -am ine o-z- z z- 3 me P_ z -o-z- z z- 3 -am p-- me o-z- z z- 3 -am p-~t=ulwriz - me o-z- z z- s 3 p-~t=u~wriz - am me o-z- z r s 3- p- =O)NHz - -aniline o-z- z r 3 n- p-~~=uyvriz - -am me o-z- z z- 3 eny ~(=NH)NHz - -amino-car oxy is acid o-r z z- s eny m- z - -ammo car oxy is acid o- r z r 3 _ -p m- z .. eny -ammo carboxylic acid o- - z H CHz_ 3 - 3_p m-w ma v.u~-w.u eny ~ -amino w m a carboxylic acid O-JVZ-Nriz ri ~riz-Sri(-~ri3)-~:ri3-v-pneny m-~~=wri)~tiz ammo carboxylic acid O-JUz-Nriz ri ~riz-~ri~-~ri3)-nn-u-pnenyi m-~~=~ri)Nriz ammo carboxylic acid o-JVZ-Nriz ri 1;ri2-l;ri(-l:rig)-Ynenyl-ammo m-l:(=V)lVriz CarDOXyIIC
acid o-~uz-Nriz n z- 3 - m-pnenyi-ammo m- z carboxylic acid O-JVZ-iVriz ri l:riz l;tl(-1;t13)-r-pnenyi-ammo m-~~=u)r~riz carboxylic acid o- z- z z- s - s-P m- z enY
-o carboxylic acid O-JVz-wtiz ri ~:riz-t,ri~-~ri3)-~:ri3-u-pnenyi-ammo m-~;~=~Jivriz carboxylic acid O-JVz-Ntiz ti ~riz-Sri(-~ri3)-tsn-u-pnenyi-ammo m-~~=u)~riz carboxylic acid o- z- z CHz-CH(-CH3)-Methyl m-C(=NH)NHz phenoxy-acetic acid ester o-SOZ-NHz H z- , - a m- z y -p enoxyacehc acid ester --o- z- z z- a - acetic iri-C(=NH)NHz ma ua a a-as a y -p epoxy=
acid ester o- z- z z- s - m-C(=NH)NHz avi ua a a.,.aJ, as a y p epoxy-acetic acid ester o- z- z z- s - m- )NHz m v~ a, ua a a..a.a, v a a Y
s--p epoxy-acetic acid ester o- z- z z- s - a m- )NHz Y ,.~ a,~~
n--p epoxy acetic acid ester o- z- z z- s - a m-C(=O)NHz y enoxyaceric acid ester o- z- z H CHz-CH(-CH3)-Methyl m-C(=U)NHz Cl-phenoxyacehc acid ester o-S~-NHz H CHz-CH(-CH3)-Methyl m- z F-phenoxyacehc acid ester o-JVi NHZ ti 1:ri2-l:tl(-Cal3)-Melllyl m-l;(=u)lVriz 1;ri3-prienOXy-acetic acid ester o-5u2 Ntiz tm :riz-pry-~ri3)-nnemyi m-~~=u)~riz ~ri3-u-pnenoxy acetic acid ester o- r z z- 3 - a m- z y n--p epoxy acetic acid ester o- r z r 3 - enoxyacetic m- z aci o- z- z r s - -p m-C(=NH)NHz epoxy-acetic aci o- z- z z- s - -p m-epoxy-acetic aci o- z- z z- s - 3- p epoxy-aceticm- NHz aci o- z- z z- s - 3- m-C(=NH)NHz -p enoXy=acettc acid o- z- z z- s - n- m- z -p epoxy acetic aci o- z- z z- s - enoxyacehc m- z aci o- z- z z- 3 - -p m- z enoxyacehc aci o- z- z ? 3 - -p m- (=O)NHz enoxyacehc aci o- z- z z- s - ,-p m- NHz epoxy-aceric aci o- z- z z- s - s--p y vy,i epoxy m-acetic acid o- z- z z- 3 - n- m--p epoxy acetic aci o- z- z z 3 - enoxyetIiano m=C(=NH)NHz o- z- z z- s - -p m-epoxy-a ano o-z- z r 3 -p m- 2 - epoxy-a ano o-z- z z- 3 3-p m-~:~=~ti)mriz - epoxy-a ano o-z- z z- , ,- p erioxy-a in~NHz - - anol o-z- z z- s n- epoxy ethanom- z - -p o-z- z z- 3 enoxye m-~:~=u)rrttz - ano o-z- z z- 3 -p m-~:~=~)Nriz - enoxye ano o-z- z r 3 -p m-- epoxy-a ano -o-z- z z- 3 ; P m- )~2 - epoxy-a ano o-z- z z- s 3- - p epoxy- m-C
- a ano o-z- z z- 3 n- epoxy- a m-C(=O~NHz - -p anol o-z- z z 3 a m_ - y w.~ awa~a.aa p epoxy-a y ether o-z- z z- 3 a m~z - Y
-p enoxye yl-ether o-~uz-Ntiz m aiz-pry-~rij)-a m- z y -p epoxy-a y ether O-JU2-Ntlz ti ~tiz-~ti(-~ri3)-enemy m- z Sri,-pnenoxy-ethyl ether O-JUZ-Nriz t m aiz -~ri3)-Memyi m-~~=rrri)r~riz cay ~n3-u-pnenoxy-ethyl ether O-JUz-Nriz t m aiz-pat(-~ai3)-nnemyi m-~~=~ri)~riz nn-u-pnenoxy ethyl ether o-~uz-lvttz t m aiz -cai3)-nnemyi m-~~=u)~riz gay rnenoxyemyi ether o-z z z- s a m- z - y -p enoxye y ether o-z- z z- s a m- =O)NHz - y -p enoxye y ether 3 x m-C =O NH
( ) 2 yethyl ether phen 3 x m O NH
z yethyl ether phen o-z- z z- 3 o m-C(=O)NHz .
phen yethyl ether o-z z z_ z p m-C(=~)NHz _ eny o_z_ , z_ z -p m_ _ eny o-z- z z z -p m- z - eny o-z- z z- z s-P m- z - enY
o-z- z z- z 3- p eny m- z - -o-z- z z- z n- enY . tn-C( NH)NHz - -P
o-z- z z- z P m- z - enY
o-z- z z- z -p m-- eny o-z z z z -p m-- eny o-z- z z- z s- P m- ~ O~z - enY
o-z- z z- z 3- - p eny m- =O)~z -o-z- z z- z n- eny m- z - -p o-z- z z- z me p-t.;(=rrti)rVtiz -o-z- z z- z -am p-C(=NH)NHz - me o-z- z z- z -am p- z - me o-z- z z- z 3-am p-C(=NH)NHz - me 2- 2 2 2 3- p-l,~=iVt1)1Vt12 - -anl llle o-z- z z- z n- p-C(=NH)NHz - -am me o-z- z z z m p-l.;(=u)mtlz - me o-z- z z- z -am p- )NHz - me o-z- z z- z -am p- z - me o-z- z z- z 3 p-~;(=u)rVriz - am -me o-z- z r z 3- p- z - -am me o-z- z r z n- p- z - -am me o-z- z z- z eny m-~~=~ri)mriz - -ammo-car oxy is acid o-z- z z- z eny m- )NHz - -ammo car oxy tc act o-~uz-NHz ri ~riz-pry-r~riz~-r-pnenyt-ammo m-~~=lrryrrriz carboxylic acid O-JVz-lVriz ri ~riz-Sri(-r~riz)-~ri3-pnenyt-ammo m-~t=ruryrrriz carboxylic acid O-JUz-lVriz ri ~riz-Sri(-r~riz)-~ri3-u-pnenyt m-~~=t~riJlrriz ammo carboxylic acid O-JUz-NHz ri ~;riz Sri(-Nriz)-tsn-u-pnenyt m-~:~=rrtyNtiz ammo carboxylic acid O-JV2 NHz i z - eny m- z -ammo car oxy tc acid o- z- z z- z - -p m- --U) eny z -ammo ,.~ ~,..
carboxylic acid o- z- z r z - -p m-C(=O)NHz eny -ammo .-..
carboxylic acid o- z- z CHz-CH~NH~-CH3-phenyl-amino m-C(=U)NHz carboxylic acid O-JVz-NHZ ri ~riz-Sri(-rVriz)-~:rt3-u-pnenyt-ammo m- z carboxylic acid O-JUy-NHZ H MHz-qty-lrriz~-rsn-u-pnenyt-ammo m-~t=u~rrriz carboxylic acid o-SOz-NHz H CHz-CH(-NHz)-Methyl m- z phenoxy-acetic acid ester o- z- z H CHz CH(-NHz)-Methyl m- z C1-phenoxyacehc acid ester o- r z z- z - a m- =NH)NHz y -p epoxy-acetic acid ester o- z- z z- z - a m-C(=NH)NHz y 3-p epoxy-ivi ua a m as acetic acid ester o- z- z z- z - a m=C(=
Y
-p epoxy-acetic acid ester o- z- z z- z - m_C(-z iva m a a v a a Y
n--p epoxy acetic acid ester o- r z z- z - m-C(=O)NHz u1 L
a y enoxyacetic acid ester o- z- z z- z - a m- =O)NHz Y
-p enoxyacehc acid ester o- z- z z- z - a m- =O)NHz Y
-p enoxyacehc acid ester o- z- z r z - a m-~,(=u)mtiz Y
,-p epoxy-acetic acid ester o- z- z r z - m-C(=O)NHz am m a m v a a Y
s--p epoxy acetic acid ester o- r z z- z - m-C(=O)NHz ma m a ar v m a Y
n--p epoxy acetic acid ester o- z- z r z - enoxyacehc m-act o- r z Z z - -p m-C:(=NH)NHz epoxy-acetic act o- z- z z- z - -p m- )NHz epoxy-acetic act o- r z z- z - 3- p epoxy-aceticm-act z- z - 3 m-C;(=NH)NHz .iv mu -p o- z z epoxy-acetic acid o- z- z z- z - n- m- z -p epoxy acetic act o- r z z- z - enoxyacehc m- )NHz act o- r z z- z - -p m- z enoxyacehc act o- z- z z- z - -p m- z enoxyacehc act z- z z- z - 3- p epoxy-aceticm- z act o- z- z z- z - m-C(=O)NHz ....
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,--p epoxy acetic acid o- r z z- z - n- m--p epoxy acetic act o- z- z z- z - enoxye m- ~=NH)NHz ano o- z- z z- z - -p m- )NHz epoxy-a ano o-z- z z- z -p m-~;(=Nn)rrnz - epoxy-a ano o-z- z z- z 3- p m-- epoxy-a ano z- z z- z 3- - p epoxy-a m- z - ano o-z- z z- z n- epoxy a m-- -p ano o-z- z z- z enoxye m-C(=O)NHz - anol o-z- z z- z -p m=C~O~NHz - enoxye anol --o-z- z z- z -p m- )Nl~
- epoxy-a ano o-z- z z- z ,- p m- z - epoxy-a ano o-z- z z- z 3- - p epoxy= m=C(=O)NHz - ethanol o-z- z z- z n- epoxy- a m=C(=OjNF
- -p ano o-z- z z- z a m-C(=NH)NHz - y p epoxy-ethyl ...
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ether o-z- z z- z m-C(=NH)NHz - iva ua a w a a y -p enoxyethyl ether o-z- z z- z a m-C(=NH)NHz - Y
-p~enoxy=ethyl ether o-~Vz-Nriz H Ltiz-Ln(-Ntiz)-a m- z y 3-p epoxy-ethyl ether o-~Uz-Nriz H Ltiz-Lti(-Ntiz)-Memyi m- z Win,-u-pnenoxy-ethyl ether o-~Uz-NHz H C;Hz-C:H(-NHz)-lV1eT11y1 m- z tin-u-pnenoxy ethyl ether o-5U2 Hz H Ltiz-~t1(-Ntiz)-nnecnyi m- z N rnenoxyemyi ether o-5Uz-NHz H caiz-c:H(-ivtiz)-Metnyma-pnenoxyemyi m- z ether o-~U2 Hz H c:Hz-LH(-NHz)-nnemyi m- z N r-pnenoxyemyi ether o-5Uz-NHz H 1:H2-l:H(-NHz)-Metriyll:rl3- m- z phenoxyethyl ether o-SUz-NHz H laiz-l:H(-NHz)-Metnyt m-1:r13-V-phenoxyethyl ether o-5Uz-NHz H l;tiz-l;tl(-iVtlz)-MeTriy1 m-~.(=u)l~nz tin-u-phenoxyethyl ether o-r z z- - p m- z n eny -o-z- z z- _ -p m-~;(=~rt)mnz n eny _ o-z- z Z - -p m- z n eny -o-z- z z- - 3 P m-~:(=~n)rvtiz n enY
-o-r z z- - 3_ _ p eny m- z n -o'z- z z- - n_ eny m- =NHjNHz n _p -o-r z z- - p m- z n eny -o-z- z z- _ -p m=C(-O)~z n eny _ o-z- z z- _ -p m- z n eny _ o-r z z- - 3- p m- =O)NHz n eny -o-r z 2 - 3_ _ p eny m- z n -o-r z z- - n_ eny m-~~=u)mnz n _p -o-z- z z- - me p- z n -o-z- z 2 - -am p-~.~=~n~mnz n me -o-z- z H Z - -am p- z n me -o-z- z z- - 3-am p-n me -o-r z z - 3- p-C~=NH)NHz n -am - me o-z- z z- - n_ p- z n _am - me o-z- z z- - m p- z n me -o-r z z- - -am p-n me -o-z- z z- _ -am p-~;(=u)wnz n me _ o-z- z z- - 3-am p- z n me -o-r z z - s- p_ =p)NHz n -~
- me o-z- z z- - n_ p- z n _m - me o-r z z- - eny m- )NHz n -ammo-car - oxy is acid o- z- z z_ n - ieny m~NH)NHz -ammo-..,.-~
.
carboxylic acid o- z- z z- n - -p m~)NHz eny -ammo ..
carboxylic acid o- z- z ~I 3_~ainino m-C(=NH)NHz carboxylic acid O-~Vz-Nriz r~ t_;tiz-jai(-tsn)-trti3-u-pnenyi m-~:l=mti)Ntiz ammo carboxylic acid o-JVz-NHz H ~alz-tai(-tsn)-tsn-u-pnenyl m- z ammo carboxylic acid O-JUz-Nriz H uriz-uty-tsn)-rnenyi-ammo m- z carooxyiic acid o-~uz-Ntiz tm aiz-pat(-tsn)-~;i-pnenyi-ammo m- z carboxylic acid o-~uz NHz ri ~riz-pry-nn)-r-pneny-ammo m-~~=u)mriz carboxylic acid o-~uz-NHz tm ;riz ~;ty-rsn)-~ri3-pnenyi-ammo m-~,~=v)r~riz carboxylic acid O-JUZ-NHZ H l;tlz-l:ri(-tSn)-C;tl3-V-prieriYl-airilIlO m-l:(=V)lVtlz carboxylic acid O-JUZ-NH2 H Ltiz-Ltil-tsn)-tsn-u-pnenyi-ammo m-~l=v)ivriz carboxylic acid o-SOz-NHz H CHz CH(-Bn)-Methyl m-C(=NH)NHz phenoxy-acetic acid ester o-~O~-NHZ H CHz-CH(-Bn)-a m- z y -p enoxyacehc acid ester o- z- z H CHz-CH(-Bn)-a m- z y -p epoxy-acetic acid ester O-~Vz-NHZ H ~;tiz-jai(-tsn)-a m- z y 3-p epoxy-acetic acid ester o-SUz-NHz H laiz-cai(-tsn)-a m- z y j--p epoxy-acetic acid ester o-5Uz NHz H ~ai2 jai(-tsn)-a m- z y n_ -p epoxy acetic acid ester o- z- z H CHz CH(-Bn)-Methyl m- z Yhenoxyacetic acid ester o- z z H CHz-CH(-Bn)-a m- z y -p enoxyacehc acid ester o- r z H CHz-CH(-Bn)-a m- z y -p enoxyacehc acid ester o-aVz NHZ ti 1;t12-lal(-tSn)-a m-Y
3-p epoxy-acetic acid ester o-~Vz NHz H Lri2 c.;til-tsn)-Metnym:rij-u-pnenoxy m-~:~=u)ivriz acetic acid ester O-JUz-NHZ H ~tiz-~ti(-tsn)-Metnyi m-~.;1=~)mriz tsn-u-pnenoxy acetic acid ester o- z- z z- n - enoxyacehc m- z aci o- z- z 2 - n - -p m- 2 epoxy-acetic -aci o- z- z z- - n - -p m- 2 epoxy-acetic aci o- z- z z- - n - 3- p epoxy-aceticm-C(=NH)NHz aci o- z- z z- - n - 3- m- z -p epoxy-acetic acid o- i z Z n - n- m- z -p epoxy acetic aci o- z- z Z n - enoXyacetic rn-C(=O)NHz act o- z- z Z n - -p m- z enoxyacehc aci o- r z z- n - -p m- z enoxyacehc aci o- z- z 2 n - ,- p epoxy-aceticm-aci o- z- z 2 n - 3--p w.~ vy.au epoxy m- z acetic acid o- z- z Z n - n- m- z -p epoxy acetic aci o- z- z z- - n - enoxye m- NHz ano o- z- z z- n - -p m-V(=Nri)wriz enoxy-a ano o- i z -H - z- n - -p m- z enoxy-a ano o- z- z z- n - 3 p m- z enoxy-a ano o- r z z- - n - s- - p enoxy-a m- z ano o- z- z r n - n- enoxy a m-~l=~ri)Nriz -p ano o- r z z- - n - enoxye m- z ano o- z- z r - n - -p m- z enoxye ano -o- r z z- n - -p m- z enoxy-a anon o- r z z- - n - 3-p m enoxy-a ano o- z- z z- n - 3 p enoxy- m- z - a ano --o- z- z r - n - n- enoxy- a m- z -p anol o- z- z z- - n - a m-C(=NH)PHz y p enoxy-ethyl ether O-JVz-Nriz t~ Lriz-~ry-tsnl-memym.i-pnenoxyemy m- z ether O-JUZ-Ntl2 ti caiz-t,til-tin)-Memyi m- z r-pnenoxy-emyi ether o-JVZ-Nti2 ti c:riz-jai(-tsn)-nnetnymai3-pnenoxy- m- z ethyl ether O-5U2-Ntl2 ti caiz-gay-tsn)-nnemym:rij-u-pnenoxy- m-~;(=ivri)wriz ethyl ether O-5u2-Ntlz ti caiz-Ltil-tsn)-Memyi m-~l=mri)~ry tsn-u-pnenoxy ethyl ether o-~u2 lvttz t~ Ltiz-~;ri(-tsn)-nnemyi m- z rnenoxyemyi ether O-JUZ-Ntlz ti Ltiz ~ail-tsn)-Metnyma-pnenoxyecnyi m-~.l=u)r~riz ether O-JUZ-Nriz t~ Lti2 Vtil-tsn)-nneyu m-~(=u)~riz r-pnenoxyemy ether O-1Uz-NtiZ tl l;tl2-l:ril-tin)-MeLriyll:rij- m-phenoxyethyl ether O-5Uz-Ntiz t1 l;ti2-fall-tfn)-lVielllyll.rl3 m-l.;l=u)1Vr12 u-phenoxyethyl ether o-5uz-lVtiz ti l;ti2-C.;til-fin)-Mettlyl m-tin-u-phenoxyethyl ether O-5Uz-Ntiz ti l;ti2-l;tll-1x12-pnenyl m-COOCH,)-O-JVZ-Ntl2 2- z- -p m- z COOCH3)- eny o-5uz lvtlz ti ~aiZ-pail-Ltiz-r-pnenyi m-~l=ivri)rrriz COOCH3)-o-5u2 lvrlz ti caiz-Ltil-Lriz-3-p m- z COOCH,)- eny o-5V2-Nri2 tl Cal2-fail-(aiz-3_ m-COOCH,)- _p eriy O-5Vz-Nri2 ti Caiz-fail-lain-n_ m-COOCH,)- -p eriy O-JUz-Nriz tm atz-~;til-caiz-p m- z COOCH3)- eny o-~uz Ntiz tt Vtiz-aril-Vriz-m-pnenyi m- z COOCH,)-o-~uz-Nttz ti t;tiz-aril-~riz-r-pnenyi m-~l=u)mnz COOCH,)-o-~uz-Nttz ti t_;tiz-aril-~tiz~:ri3-pneny m-~:l=u)mriz COOCH,)-o-auz ivtiz m ;tiz-pail-~ti2-~ai3-u-pnenyi m-~.l=u)ivriz COOCH,)-o-~u2 Ntiz ti Vtiz-aril-uriz-tsn-u-pnenyi m- z COOCH3)-o-~uz-iVttz ti z- Z- 1 p-COOCH3)- me o- z- z z- z- -and me p-COOCH3)-o-~uz-lvrlz l:riz-pry-l:riz-r-anllme p- z COOCH3)-o-~uz-NHz ti l:riz-qty-~;tiz-l:ri,-anllme p-~~=mryvriz COOCH3)-o-~Uz-NHz H C;H2-C;H(-C;HZ-C;H3-V-amlme p-C:(=NH)NH2 COOCH,)-o- r z z- z- n- -am me p- z COOCH,)-O-JU2-1VI12 H 1x12-l:rl~-l;rly-Anllme p-~;~=uyvtiz COOCH,)-o-~uz-lvriz r z- -and me p- z COOCH,)-o-~uz-lvtiz r z- -am me p- z COOCH3)-o-JUZ-NHZ z- z- 3-ant me p-COOCH3)-O-JUZ-NHZ ri l;riz-l:ri(-l:riZ1:r13-U-anllme p-l:(=U)lVriy COOCH,)-O-JUZ-Ntiz H lalz-l:ri(-1;r12-tan-u-anllme p-COOCH3)-O-JVz-NHz H lair-l:ri(-C;tlz-Ynenyl-ammo-CarDOXyIICm- y COOCH3)- acid o-JVz NHz H 1x12-lal(-1x12-eny -amino m-COOCH3)- carboxylic acid O-JUZ-NHZ H l.al2-lal(-l.rlzr-pnenyl-ammo m-1.~=lVtlJlvriz COOCH3)- carboxylic acid o-SOz-NHz H C;Hz-C;H(-C;Hz-C;H3-phenyl-aminom-C;(=NH)NHz COOCH3)- carboxylic acid o-JVZ-NHZ ti l:Hy-l:H(-l:Hzl:ri3-u-pnenyl m-ammo COOCH3)- carboxylic acid o-~Uz NHz H l:Hz-1:H(-c:Hz-tsn-u-pnenyl m-1:~=mriJwriz ammo COOCH3)- carboxylic acid O-JVZ-NHZ H I:HZ l:H(-Calz-Yneriyl-ammo m-1:~=U)1Vr12 CarDOXynC
COOCH3)- acid O-JVZ-NHz ti l;Hy-l:H(-l:Hzl:l-prieriyl-ammom- y -COOCH3)- carboxylic acid O-JUZ-NHz ti laly-l:ri(-l;tlzr-pneriyl-ammo m-COOCH,)- carboxylic acid o-JVZ-NHZ H C.;HZ lal(-l;tlZ-1:ri3-prienyl-ammom-COOCH,)- carboxylic acid o-JUZ-Ntiz H C:HZ-Cal(-1x12-l:rij-U-prienyl-ammom-1~~=U)lVrlz COOCH3)- carboxylic acid o-JUy-NHZ H l:Hz l:ri~-l;tiZ-tiri-V-pnenyl-ammom-L(=UJlvriz COOCH3)- carboxylic acid o- Oz-NHz H C;Hz-C;H(-C;Hz-Methyl phenoxy-aceticm-C:(=NH)NHz COOCH,)- acid ester o-SOz-NHz H C;Hz-C;H(-C;Hz-Methyl (:1-phenoxyacehcm-(:(=NH)NHz COOCH3)- acid ester o- Oz-NHz H CHz-C:H(-CHz-Methyl >'-phenoxy-m- z acetic COOCH3)- acid ester o-JUZ-NHZ H 1;H2-lal(-lalZ-MeLtlyll:ri3-prienOXy-m-COOCHj)- acetic acid ester O-JUz-NHz H l:HZ-l:ry-l:riz-Memyll:ri3-U-pnenoxy-m-1:~=lrryvriz COOCH,)- acetic acid ester o-JVZ-Ntl2 H 1:ri2-l:ri(-1x12-Memyl tin-V-pnenOXym-l:(=lVr1)lVtlz COOCH3)- acetic acid ester o-SOz-NHz H (:Hz-LH(-C;Hz-Methyl Yhenoxyacehcm-C;(=U)NHz COOCH3)- acid ester o-SUz-NHz H C;Hz C;H(-C:Hz-Methyl C;1-phenoxyacehcm-C;(=V)NHz COOCH3)- acid ester o- z- z z- z- m- z au m ua a m am .~ v~maa a y -p enoxyacehc COOCH3)- acid ester O-JVZ-wtiz ri ~,riz-~;ril-~riz-Memy ~ri3-pnenoxy-m-~:l=vyvriz COOCH,)- acetic acid ester O-JVZ-wtiz ri ~;riz-~;ril-~;riz-nnetnym:ri3-V-pnenoxym- z COOCH3)- acetic acid ester o-~uz-Nriz r~ t,riz-~;til-~;ttz-a y n_ _p epoxy m- z COOCH3)- acetic acid ester o-SUz-NHz H CHz CH(-CHz-Yhenoxyacehc m-C(=NH)NHz acid COOCH,)-o-SOz-NHz H CHz CH(-CHz-Cl-phenoxy-acehcm-(:(=NH)NHz acid COOCH3)-o-SOz-NHz H CHz-CH(-CHzr-phenoxy- acehcm-C(=NH)NHz acid COOCH3)-o-SUz NHz H CHz-CH(-CHz-CHj-phenoxy-acehcm-C(=NH)NHz acid COOCH,)-o-SOz-NHz H CHz-CH(-CHz-CH3-U-phenoxy-acehcm-C(=NH)NHz COOCH,)- acid o-SOz-NHz H CHz-CH(-CHz-13n-U-phenoxy m- z acehc acid COOCH,)-o-SOz-NHz H CHz-CH(-CHzenoxyacehc aci m- z COOCH,)-o-SOz-NHz H CHz-CH(-CHz-Cl-phenoxyacehc m- z acid COOCH,)-o-SOz~VHz H CHz-CH(-CHz-p enoxyacehc m- z aci COOCH3)-o- Z z H CHz-CH(-CHz-3-p epoxy-acehc m- z aci COOCH3)-o- z- z H CHz CH(-CHz-3 -p epoxy acehcm- z COOCH3)- acid o- z- z H CHz CH(-CHz-Bn-U-phenoxy m- z acehc acid COOCH,)-o-JVz-Ntlz r z- enoxye ano m- z COOCH3)-o-JVz-Nriz ti Lriz-Lnl-unz-ul-pnenoxy-emanoim-~l=~ryrrriz COOCH3)-O-JUZ-Nriz rm aizway-~riz--p epoxy- a ano m- z COOCH3)-O-~Uz-Nriz ti ~tiz-c:ry-c:riz-3-p epoxy-a ano m- z COOCH,)-o-JVz-Ntiz ti ~;tiz cailwaizwai3-V-pnenoxy-emanoim- z COOCH3)-o-~Vz-Nriz ti LrirLril-Lnz-~n-V-pnenoxy m-~l=rrri)wriz etnanoi COOCH3)-O-JUZ-Nriz H (a12-fall-l;tl2-rnenoxyemanoi m-~l=VJr~riz COOCH,)-O-JV2 Ntl2 t1 l;rii l;tll-l~riz--p eriOXye ano m-COOCH3)-O-JUz-Nriz ri z z- -p epoxy-a ano m- z COOCH3)-O-JVZ-Ntl2 ti z 2- y-p epoxy-a ano m- y COOCH3)-O-JUZ-NHZ n z- z- ,- -p epoxy- m- z a ano COOCH,)-o-JVz-NtlZ Z- z- n- -p epoxy- m- z a ano COOCH3)-O-JVZ-NHZ ri ~tiz-aril-~riz-nnemyi pnenoxy-emyim- z COOCH,)- ether O-JUZ-NH2 tm ;tiz-pail-~;riz-nnetnyma-pnenoxyemyim- z COOCH,)- ether o-JUZ-NHZ ri 1:ri2-l:ril-l:rizlVlelllyl r-pnenOXy-eTIly1m-COOCH,)- ether o- z- z z- z- a Y 3 p enoxy- m- z COOCH,)- ethyl ether O-JUZ-Nriz ri ~riz-Sri(-~;riz-nnemym;rt3-u-pnenoxy-m-~;(=mtyvtiz COOCH3)- ethyl ether O-JUZ-lVri2 z- r a y n- -p enoxy m- z COOCH,)- ethyl ether ~''1U2-Nri2 ri ~'riz-Lri(-~'ri2-nnemyi rnenoxyemyim-~(=u~Nriz COOCH3)- ether O-JUz-Nri2 z- r a y -p enoxye m- z y COOCH3)- ether O-JU2-lVri2 z- z- a y -p enoxye m- z y COOCH,)- ether o-~uz-Nriz r~ ~riz-Sri(-~riZenemy ~ri3- m-~(=u~Nriz COOCH3)- phenoxyethyl ether o-~uz-Nriz r~ ~riz-Sri(-~riz-enemy ~rt3-u- m-~(=u~Nriz COOCH,)- phenoxyethyl ether o-~uz-mtiz t-~ ~tiz-Lti(-LriZMemy tsn-u- m-~(=uyvtiz COOCH3)- phenoxyethyl ether o-~uz-Ntiz t-~ Ltiz-~;ti(-trriz-pneny m-~(=mryvriz CHz-OH)-o-~uz-mriz t~ Ltiz-Lti(-~tiz-m-pnenyi m-~(=mryvriz CHz-OH)-O-JUz Ntiz ri ~riz-Sri(-~riz-r-pnenyi m-~(=NryNriz CHz-OH)-o-~uz-mtiz rt ~riz-~ti(-Ltiz~;ti3-pnenyi m-~(=mryvriz CHz-OH)-O-JUZ-Nriz ri ~:riz-Sri(-~:riz-~;ri3-u-pnenyl m- z CHz-OH)-O-JUz-Nriz z- z- n- -p eny m- z CHz-OH)-o-JUz-Nriz n ~tlz-~;t1(-~alz-pnenyi m- z CHz-OH)-O-~UZ-Ntl2 2- Z- -p eny m- z CHz OH)-O-JUz-Nriz z- z- -p eny m- z CHZ OH)-O-~uz-Nriz ri ~riz-Sri(-~riz-~ri3-pnenyi m-~(=u~Nriz CHz OH)-o-~uz-mriz z- z- 3- -p eny m- z CHz OH)-O-JUz-Nri2 t~ c:riz-Sri(-~tiz-~n-u-pnenyi m-~(=u~Nriz CHz-OH)-o-~uz-Ntiz t~ ~riz-Sri(-~riz-.mime p- z CHz-OH)-o-~uz-Ntiz ri ~riz-~ti(-~riz-m-amine p- z CHz-OH)-o-~uz Ntiz ti ~tiz-Sri(-~tiz-r-amnne p-~(=Nri~Ntiz CHz-OH)-o-~uz-Nriz ti ~riz-Sri(-~riz-~ri3-amine p-~(=Nri~Nriz CHz-OH)-o-~uz-Ntiz ti ~tiz-Sri(-~riz-~ri3-u-amine p-~(=NryNriz CHz-OH)-O-JUz-iVriz n ~riz-~ry-~riz-nn-u-anume p- z CHz-OH)-o-~uz-Nriz n ~riz-Sri(-~riz-amine p- z CHz OH)-O-JUz Nriz n ~riz Sri(-~riz-m-amine p- z CHZ OH)-O-JVz-Nriz n ~riz-Sri(-~riz-r-amine p- z CHZ OH)-o-auz iVtiz i z- 3 am me p- z CHz-OH)-o- z- z r z- 3- -am me p- z CHz-OH)-O-JUZ-Nriz ri ~riz-Sri(-~riz-tsn-u-amime p-~(=u)Ntiz CHz-OH)-o-~uz-wriz r~ ~riz-uti(-Vriz-rnenyt-ammo-carnoxyncm-u(=Nti)Nriz CHz-OH)- acid O-JU2-lVIlz h 1;ri2-lal(-l:riz-m-rnenyi-ammo m-u(=Nri)wriz CHz-OH)- carboxylic acid o-~uz-~riz n ~riz uri(-~riz-r-pnenyi-ammo m-~(=Nri)Nriz CHz-OH)- carboxylic acid O-JUZ-ivriz ri ~;riz-~:ri(-~riz-~ai3-pnenyi-armnom-t,(=~ti)Nriz CHz-OH)- carboxylic acid O-JUZ-ivriz ri z- z- 3- _p eny ammo m- z CHz-OH)- carboxylic acid o-~uz-Nriz n ~riz-Sri(-~riz-rsn-u-pnenyi m-~(=r~ri)wriz ammo CHz-OH)- carboxylic acid o-auz-Ntiz z- z- eny -ammo car m- z oxy is CHz-OH)- acid o-~uz Ntiz tm ;ttz-~:ri(-~;tiZ-p eny -ammo m- z CHz-OH)- carboxylic acid o-auz-Nriz n ~riz-uri(-uri2-p eny -ammo m- z CHz-OH)- carboxylic acid o-~uz-Ntiz ti ~riz-~ry-~riz~ri3-Pneny-ammo m- z CHz-OH)- carboxylic acid o-~uz-Ntiz t~ uriz-uri(-uriz-~ri3-u-pnenyi-ammom-~(=u)~riz CHz-OH)- carboxylic acid o-~uz-Ntiz ti uriz ury-~riz-~sn-u-pnenyi-ammom-~(=u)~riz CHz-OH)- carboxylic acid o-SOz-NHz H CHz-CH(-CHz-Methyl phenoxy-aceticm-C(=NH)NHz CHz-OH)- acid ester o-SOz NHz H CHz-CH(-CHz-Methyl Cl-phenoxyacehcm-C(=NH)NHz CHz-OH)- acid ester o-SOZ NHz H CHz-CH(-CHz-Methyl i'-phenoxy-m-C(=NH)NHz acetic CHz-OH)- acid ester o-~uz 1Vt12 H 1,ri2-l.tl(-1,t12-a Y j-p enoxy- m- z CHz-OH)- acetic acid ester o-~uz-ivriz m aiz-jai(-~aizmemyai3-u-pnenoxy-m-~.(=mri)~riz CHz-OH)- acetic acid ester o-~uz-Ntiz ti uriz-cai(-~:riz-Merry rsn-u-pnenoxym-~:(=r~ri)rrriz CHz-OH)- acetic acid ester o- z-NHz H CHz-CH(-CHz-a y enoxyacehc m- z CHz-OH)- acid ester o-SOZ NHz H CHz-CH(-CHz-a y -p enoxyacehcm- z CHz-OH)- acid ester o-SOz-NHz H CHz-CH(-CHza y -p enoxyaceticm- z CHz-OH)- acid ester o-~uz-Ntiz t~ ~riz-~:ri(-~riz-a Y s-p enoxy- m- z CHz-OH)- acetic acid ester o-~u~ NHz tm aiz-~:ri(-~rizenemy ~ri3-u-pnenoxym- z CHz OH)- acetic acid ester o-JUz NHZ H C;ri2-lal(-1x12-Merry tsn-u-pnenoxym-~(=u)~riz CHz-OH)- acetic acid ester o-SOz-NHz H CHz-CH(-CHz-Yhenoxyacetic m-C(=NH)NHz acid CHz-OH)-o-SOz-NHz H CHz-CH(-CHz-Cl-phenoxy-aceticm-C(=NH)NHz acid CHz-OH)-o-SOz-NHz H CHz CH(-CHz-r-phenoxy- aceticm-(:(=NH)NHz acid CHz-OH)-o-SOZ NHz H CHz-CH(-CHZCH3-phenoxy-aceticm-C(=NH)NHz acid CHz-OH)-o-SUz-NHz H CHz-CH(-CHz-CH3-U-phenoxy-aceticm-C(=NH)NHz CHz-OH)- acid o-z- z r z- n- -p epoxy aceticrii=C~~HjNHz aci CHz-OH)-O-JUy-Nt12 ~tiz-~ti(-~tiz-enoxyace c aci m- z OH)-o-SOz-NHz CHz-CH(-CHz- Cl-phenoxyaceLc m- z acid CHZ
OH)-o-SOz-NHz H CHz-CH(-CHz- F-phenoxyacehc m- z acid CHz-OH)-o-SUB H CHz-CH(-CHZ CH3-phenoxy-aceticm-C(=U)NHz acid CHz-OH)-o-SUZ-NHz H CHz-CH(-CHz- CH3-U-phenoxy m-C(=U)NHz acetic CHz-OH)- acid o-SUz-NHz H CHz-CH(-CHz- 13n-U-phenoxy m-(:(=U)NHz acetic acid CHz OH)-o-~uz-Ntiz ri ~riz-~nl-Lnz- rnenoxyemanoi m-~:(=mrywriz CHz-OH)-o-5u2 Hz t~ Ltiz-Lti(-Vtiz-m-pnenoxy-emanoim- z N
CHz-OH)-o-5Vz-Nriz t~ z- z- -p epoxy- a ano m- z CHz-OH)-o-~u2 Hz z- z- s-P epoxy-a ano m- z N
CHz-OH)-o-JUz Hz t1 Ltlz-Lt1(-Lt12 ~;ti3-U-pnenoxy-emanoim-~,(=mryvriz N
CHz-OH)-O-JU2-Ntlz r~ ~tiz-~ty-~nz n- -p epoxy a m- z ano CHz OH)-o-JUz-NHz ti z- z- enoxye ano m- z CHz OH)-o-5U2-Nriz tm :riz-Lril-Lriz-~-i-pnenoxyemanoim-~:(=~yvriz CHz-OH)-O-JUZ-NHz t1 2- z- -p erioxy-a ano m-CHz-OH)-O-5U2-Nt12 H 1;t12-lal(-l:riz-3 p erioxy-a m-ario CHz-OH)-o-5Uz-Nri2 ti t;riz tiz-3- -p epoxy- m- z Lti(-L a ano CHZ
OH)-O-JUZ-Ntlz tt ~riz-~nl-~nz- nn-u-pnenoxy- m- z emanoi CHz OH)-o-5u2 Hz H t;tiz-cai(-Ltiz-Memyi pnenoxy-etnyim-~(=Nri~wriz N
CHz-OH)- ether o-~uz-tvtiz ti ~tiz-Vti(-~riz-enemy m-pnenoxyeyum-~(=mryvriz CHz-OH)- ether o-~uz-Ntiz t~ catz-Lti(-Lttz-nnemyt r-pnenoxy-emyim- z CHz ether OH)-o-~uz tiz ti ~riz-pry-~riz nnemyi ~ri3-pnenoxy-m- z N
CHz-OH)- ethyl ether o-5u2 ttz tm aiz-Lti(-Ltiz a y 3- -p epoxy-m- z N
CHz-OH)- ethyl ether o-JUz-Ntiz H z z- a y n- -p epoxy m- z CHz-OH)- ethyl ether o-z- z z- z- a y enoxye y m-C(=O)NHz CHz-OH)- ether O-JUz-Nriz H t;tiz iz- nnetnym;i-pnenoxyemyim-~(=~~wriz Lti(-ca CHz-OH)- ether O-JUZ-Nri2 H caiz tiz-a y -p enoxye m- z Vti(-~ y CHz-OH)- ether o-JUZ-NHZ H 1:ri2-l;tl(-l;riz-MeTnyll;ti3- m-CHz-OH)- phenoxyethyl ether o-JUZ-NHZ H 1:ri2-1;t1(-1:ri2-Metnym;ti3-u- m-~(=u~wnz CHz-OH)- phenoxyethyl ether O-~Uz-Nttz H Ltiz-Vt1(-Vtlz-nnetnyi nn-u- m-~(=U~wriz CHz-OH)- phenoxyethyl ether o- z- z z- r P enY m-l:l=wri)wriz C(=O)-N-morpholino)-o-~uz-Ntiz tm _;tiz-l;til-l;riz-la-pnenyi m-l:l=wti)wriz C(=O)-N-morpholino)-o-~uz-Nriz r~ l:riz l;ril-l;riz-r-pnenyi m-l:l=wri)wriz C(=O)-N-morpholino)-O-JUz wtiz t~ l:riz-l;ril-l:rizl:ri3-pnenyi m-1:1=wri)wriz C(=O)-N-morpholino)-O-JUy-writ H lalz l;til-laiz-l;ti3-u-pnenyi m-l:l=wri)wriz C(=O)-N-morpholino)-O-JUz-Nriz ti l;tiz-l:ril-l:riz-tsn-u-pnenyi m-l:l=wri)wriz C(=O)-N-morpholino)-O-JVy-writ ti l:riz-l:ril-l:riz-pnenyi m-l:l=u)wriz C(=O)-N-morpholino)-O-JVZ-wtlZ ti l;rtz-l:ril-~riz-la-pnenyi m-l:l=v)wriz C(=O)-N-morpholino)-O-JUZ-Ntly ti l;tiz-l;ttl-c:riz-r-pnenyi m-1:1=u)wriz C(=O)-N-morpholino)-o-5Vz-wtlz t~ ~;t~z-l;til-l;tiz-l:rt3-pneny m-l,l=u)wtiz C(=O)-N-morpholino)-O-JVZ wtly tl lal2-fall-(:tiz-lalg-u-prienyl m-l.l=V)wrlz C(=O)-N-morpholino)-O-JUZ-writ t~ t,tiz-fail-l;tiz-nn-u-pnenyi m-1:1=u)wriz C(=O)-N-morpholino)-m me Jv 1aa aW .aW .aa~-W !~ a vl awy.u o- z- z a p- z Z- z-C(=O)-N-morpholino)-o-~uz-ivrtz tm ;rtzw:ryuatzwa-amime p-1,1=wti)wtiz C(=O)-N-morpholino)-O-~UZ-Nriz ri l:riz-l:ril-l:rizr-amime p-l:l=wri)wriz C(=O)-N-morpholino)-o-~uz-wry r~ l:riz-l:ril-l:riz-l:ri3-amnne p-1.1=lVr1)lvriz C(=O)-N-morpholino)-O-JVZ-wriz ri ~riz-l;til-l:riz-l:ri3-u-amime p-1,1=wn)wriz C(=O)-N-moipholino)-O-JVZ-writ ti 1.r12-l:rll-l:rlz-tsn-u-amime p-1.1=lVr1)1vr12 C(=O)-N-morpholino)-O-JUz-wriz tl lai2-l;tll-l:rlz-Anllllle p-lJl=V)wrl2 C(=O)-N-morpholino)-O-JVZ-wriz t~ t;tiz-l:ril-l.;riz-la-amime p-l:l=u)wriz C(=O)-N-morpholino)-o-auz wtiz ri 1.t12-1.111-1.r12-r-amime p-1:1=u)wriz C(=O)-N-more o mo -o-JVZ-rrHz ri ~riz-Sri(-MHz-LH3-amime p-~:~=Vyvtiz C(=O)-N-morpholino)-O-JVz-lvHz H ~riz-uH~-c:Hz-uH3-u-amime p-~l=u)wriz C(=O)-N-morpholino)-o-JUz-NHz H ~aiz-~:H(-~;Hztsn-u-amime p-t,(=Vyvtiz C(=O)-N-morpholino)-O-5Uz-NHz H l;Hz C:H(-l:Hz-Yneriyl-amln0-CarUOXyIICm-l:(=lVr1)lVtiz C(=O)-N- acid morpholino)-o-SU2lvHz H ~:Hz-LH(-c:Hz-ta-rnenyi-ammo m-~;~=wrywriz C(=O)-N- carboxylic acid morpholino)-o-~Uz-NHz H ~:r12 ~:rt(-t_;rlz-r-pnenyl-ammo m-~~=wryvriz C(=O)-N- carboxylic acid morpholino)-o-5Vz NHz H l;Hz-l:H(-l:Hzuric-pnenyi-ammom-~~=wriJwriz C(=O)-N- carboxylic acid morpholino)-O-SUz-NHz H l;Hz-l:H(-l;HZ-1:ri3-V-prienyl m-l;(=lVr1)lVrlZ
ammo C(=O)-N- carboxylic acid morpholino)-o-5uz lvHz H uHz-LH~-LHZrsn-u-pnenyi m-~~=Nrywriz ammo C(=O)-N- carboxylic acid morpholino)-o-5uz ivHz H LHz-uH(-LHz-rneny-ammo carnoxyncm-~~=u~wriz C(=O)-N- acid morpholino)-O-JUz-1VHZ H lalz-l;tl(-l;tiz-l:l-pneriyl-ammom-~.~=u)lvtlz C(=O)-N- carboxylic acid morpholino)-O-JVz-NHz H l:Hz-l:H~-l;Hz-r-pnenyl-ammo m-l:~=V)iVtlz C(=O)-N- carboxylic acid morpholino)-O-~Uz-NHz H ~:Hz-LHl-~-Hr~H3-Pneny-ammo m-~,~=vyvriz C(=O)-N- carboxylic acid morpholino)-O-JVz-NHZ H l:Hz t;H(-Calz-C:H3-V-prieriyl-ammom-l:~=VJlvrlz C(=O)-N- carboxylic acid morpholino)-O-JVz-NHz H (:Hz-C:H(-l;Hz-tin-V-pnenyl-ammom-~:~=u)iVtiz C(=O)-N- carboxylic acid morpholino)-o-SOz-NHz H CHz-CH(-CHz-Methyl phenoxy-aceticm-C;(=NH)NHz C(=O)-N- acid ester morpholino)-o-SOz-NHz H CHz-CH(-CHzMethyl Cl-phenoxyacehcm-C(=NH)NHz C(=O)-N- acid ester morpholino)-o-SUz-NHz H CHz-CH(-CHz-Methyl )~~-phenoxy-m-C(=NH)NHz acetic C(=O)-N- acid ester morpholino)-O-JVZ-lVriz ri l.,rlz-l.rl(-l.tlz-Memyi ~ri3-pnenoxy-m-l:(=lvtl)lvriz C(=O)-N- acetic acid ester morpholino)-O-JUZ-mri2 ri ~;riz ~;ri~-~:riz-memym:ri3-v-pnenoxy-m-~,1=mryvriz C(=O)-N- acetic acid ester morpholino)-~SO~-P -~ ~ CHz-CH(-CHZ-Methyl gn-O-phenoxym- =NH NHz ~ ~ ~
aceric aci ester -a moipholino)-o-SOz-NHz H CHz-CH(-CHz-Methyl Phenoxyacehcm-C(=U)NHz C(=O)-N- acid ester morpholino)-o-SOz-NHz H CHz-CH(-CHz-Methyl Cl-phenoxyaceticm-(:(=U)NHz C(=O)-N- acid ester morpholino)-o-SOz-NHz H CHz-CH(-CH2Methyl F-phenoxyaceticm-C(=U)NHz C(=O)-N- acid ester morpholino)-o-~uz-Ntiz m :riz-~til-~;tizmemym:ri3-pnenoxy-m-~l=~~wriz C(=O)-N- acetic acid ester morpholino)-O-JVZ-NHZ H MHz-aril-~riz-nnemyi ~ri3-u-pnenoxym-~l=v~wriz C(=O)-N- acetic acid ester morpholino)-o-~UZ Ntlz H ~riz-aril-~riz-enemy rsn-v-pnenoxym-~l=v~wriz C(=O)-N- acetic acid ester moipholino)-o-SOz-NHz H CHz-CH(-CHz-Phenoxyacehc m-C(=NH)NHz acid C(=O)-N-morpholino)-o- z- z H CHz-CH(-CHz-Cl-phenoxy-aceticm-C(=NH)NHz acid C(=O)-N-morpholino)-o- z-NHz H CHz-CH(-CHz-r~-phenoxy- aceticm-C(=NH)NHz acid C(=O)-N-morpholino)-o-S~NH2 H CHz-CH(-CHz-CH3 phenoxy-aceticm-(:(=NH)NHz acid C(=O)-N-morpholino)-o-~~-NH2 H CHz-CH(-CHz-CH3-U-phenoxy-aceticm-(:(=NH)NHz C(=O)-N- acid moipholino)-JV 111 1W .11 vi~-W 1J v 11 a v' avaa~W
o- z- z n- -p epoxy aceticm- z z- z- aci C(=O)-N-morpholino)-o-SOZ NHz H CHz CH(-CHz-Yhenoxyacehc m-C(=U)NHz acid C(=O)-N-morpholino)-o-SOZ-NHz H CHz-CH(-CHz-Cl-phenoxyaceticm-C(=U)NHz acid C(=O)-N-morpholino)-o- z- z r r -p enoxyacetic m-C(=O)NHz acid -.- ~.
C(=O)-N-morpholino)-o-SOz-NHz H CHZ CH(-CHz-CH3-phenoxy-aceticm-C(=U)NHz acid C(=O)-N-morpholino)-o- z-NHz H CHz-CH(-CHz-CH3-U-phenoxy m-C(=U)NHz acetic C(=O)-N- acid motpholino)-o-SOz-NHz H CHz-CH(-CHz-Bn-U-phenoxy m-C(=U)NHz acetic acid C(=O)-N-morpholino)-O-JUz-Nriz H ~riz-~nl-~nz-rnenoxyemanoi m-~l=~rywriz C(=O)-N-moipholino)-.
O-JVZ-NHZ H 1:H2-l;Hl-l:riz-l:l-pneriOXy-elllanolm-l:l=lVtlJlVtlz ' C(=O)-N-morpholino)-o- z- z z- z- -p enoxy- et in~(=lQHjRHz iano C(=O)-N-morpholino)-O-JVz NHz H l;Hz-l:Hl-l;Hz-1;H3-pneriOXy-eTtlanolm-l:l=1VH)lVHz C(=O)-N-morpholino)-O-JUZ-NHZ H C:HZ-l;Hl-1:H2-1:H3-V-prienoxy-etrianotm-~:l=1VH)1VH2 C(=O)-N-morpholino)-O-JUZ-NHZ H l.Hz-C:HI-(:HZ-lin-V-pnenOXy m-l:l=1VH)1VH2 elllanol C(=O)-N-morpholino)-O-JVZ-NHq H l:Hz-l:Hl-l;Hz-YnenOXyeTClan01 m-l.;l=V)lVHy C(=O)-N-morpholino)-O-JUz-NHy H l:Hz-l:Hl-l;HZ-l;l-prieriOXyelllan0lm-l.;l=V)iVH2 C(=O)-N-morpholino)-o- z- z z- z- -p enoxy-a ano m- z C(=O)-N-morpholino)-O-5Uz NHZ H l:Hz-(:Hl-l:Hz~H3-pnenoxy-etnanoim-~l=v)~Hz C(=O)-N-morpholino)-o-5Uz-NHz H ~:HZ LHl-~:Hz-LH3 U-pnenoxy- m-~:l=v)~Hz emanoi C(=O)-N-morpholino)-o-SUz NHz H ~:Hz-LHl-~;Hz-tsn-u-pnenoxy- m-~:l=v)mHz emanoi C(=O)-N-morpholino)-o-JVz-Nriz H ~:Hz LHl-~:HZ-nnemyi pnenoxy-emyim-~,l=mH)mHz C(=O)-N- ether morpholino)-O-~Uz-NHz H ~:HZ-~:Hl-~:HZ-Metnyma-pnenoxyemyim-~.~=mri)mriz C(=O)-N- ether morpholino)-o-~uz-lvHz H LHZ-LHl-LHZ-Memyi r-pnenoxy-emyim-~l=~H)mHz C(=O)-N- ether morpholino)-o-~uz NHz H ~HZ-~Hl-~HZiviemyi ~H3-pnenoxy-m-~l=mH)mriz C(=O)-N- ethyl ether morpholino)-o-~Uz-NHz H 1.:H2-(:Hl-1;H2-Metnym:H3-u-pnenoxy-m-~:l=r~ri)r~Hz C(=O)-N- ethyl ether morpholino)-o-~uz-mHz H t~HZw:HI-t.HZ-mecnyi ~sn-v-pnenoxym-~.l=mH)mnz C(=O)-N- ethyl ether morpholino)-O-JUz-NHz H l:Hz-l;Hl-liH2-lVleitlyl YrieriOXyeTriylm-l:l=V)lVHz C(=O)-N- ether morpholino)-O-JUZ-NHZ H l:Hy-l:Hl-1;H2-nnemyi m-pnenoxyemyim-~l=v)~Hz C(=O)-N- ether morpholino)-O-JUZ-NHZ H t,Hz-c:Hl-~;Hz-nnemyi r-pnenoxyetnyim-~l=~)mHz C(=O)-N- ether morpholino)-O-1Uz-NHZ H 1:H2-l:Hl-1;H2-nnemyi ~H,- m-~l=v)mHz C(=O)-N- phenoxyethyl ether morpholino)-O-JUZ-NHZ H C;Hz-l:Hl-1:H2-MetClyll:Hg-V- m-C(=O)-N- phenoxyethyl ether more o mo -o- z- z z_ z_ a y n_ - m-C(=O)NHz ... u. . ..~
~, C(=O)-N- phenoxyethyl ether moipholino)-o-SUZ-NHZ H 1;H2-l:H(-1:ri2-phenyl m-CHz-S(O)z-CH, o-5Vz-NHz z- z- -p eny m- z CHz-S(O)z-CH3 o-~Uz-NHz H C:HZ-C.;H(-C;HZ-r-pnenyi m-~(=rVri)rrriz .
CHz-S(O)z-CH3 o-~U2 NHz ri UriZ c:ri(-uHz-3-p eny m- z CHz-S(O)z-CH3 o-~V2 NHz ri z z- 3- -p eny m- z CHz-S(O)z-CH3 o-SUZ-NHZ H 2_ 2_ n_ _p eny m- z CHz-S(O)z o-5Uz-NHz H l:riz-t;ri(-C:riz-phenyl m-~;(=u)rVriz CHz-S(O)z-CH3 o-5Vz NHz H l:riz-C.;ri(-1:H2--p eny m-CHz-S(O)z o-5Uz-NHz H ~riz-c:ri(-~riz-r-pnenyi m- z CHz-S(O)z-CH3 o-5Uz-NHZ H ~riZ-Sri(-~riz-~ri3-pnenyi m-~(=u)mriz CHz-S(O)z-CH3 o-5Uz-NHz H Lriz-Lri(-~riz-~ri3-u-pnenyi m- z CHz-S(O)z-CH3 o-SUZ NHZ H C:riz l;H(-l:riz-n_ _p eny m- z CHz-S(O)Z
o-SUZ NHz H CJHz t;ri(-c,riz-m me p- z CHz S(O)z o-~UZ NHz H C:HZ c:H(-t;Hz_-am me p- z CHz-S(O)z-CHj o-SUz-NHz H C:Hz-C:H(-t.riz_-am me p- z CHz S(O)z CH, o-SUz-NHz H c:Hz-c:ri(-C:riz-3-am me p- z CHz S(O)Z
CH, o-SUz-NHz H c:riz Lri(-c:riz-3- -am me p- z CHz S(O)z CH, o-5U2-NHZ H C:HZ-l:H(-(:HZ-n_ -am me p-CHz S(O)Z
CH, o-SU2 NHz H z z- m me p- z CHz-S(O)z-CH3 o-5U2 NHz H c:riz t;ri(-c:riz-W -amtme p-l.(=V)1Vt12 CHZ S(O)z CH, o-5Uz NHz ri C:Hz-C:ri(-l;riz-r-anllme p- z CHz-S(O)z-CH3 O-5Uz-Nriz H c:riz-Sri(-~riz-~ri3-amime p- z CHz-S(O)z-CH3 o-5uz-NHz ri Lriz-Sri(-~riz-~ri3-u-amime p- z CHz-S(O)z-CHj o-5Uz-Nriz H (:Hz-Lri(-Lriz-tsn-u-amlme p- z CHz-S(O)i o-SUz NHz H Lriz c:ri(-~ri2-rnenyi-ammo-carooxyiicm- z CHZ S(O)z-CH3acid o-SUz-NHz H (_;riz-cJri(-LHz-eny -ammo m- z CHz-S(O)z-CH3carboxylic acid O-SUZ-NHZ H l;riz-l:ri(-1:H2-r-pnenyi-ammo m-~~=rrri)ivriz CHz-S(O)z-CH3carboxylic acid o-SUZ NHz H c:riz Lri(-~;riz-3 p eny -ammo m- z CHZ S(O)z-CH3carboxylic acid o-SUz-NHz H C:HZ ~;H(-~:riz-3- -p eny ammo m- z CHz-S(O)z-CH,carboxylic acid o- z- z z- z- n- -p eny ammo m-l:l=~rywriz CHz-S(O)z-CH,carboxylic acid o-~uz-Ntiz ti laiZ l:ri(-laiz-Yneny-ammo carnoxyucm-l:l=u~Nriz CHz-S(O)Z acid CH, o-~uz-Nriz ri l:riz-l:ril-l:riz-m-pnenyi-ammo m-l:l=uJ~riz CHz-S(O)z-CH,carboxylic acid o-~u2 Nriz ri l:riz-l:ril-~riz-r-pnenyi-ammo m-~l=u~r~riz CHz-S(O)z-CH3carboxylic acid O-JVZ-lVtlz H 1x12-fall-lalz-l:ri3-pnenyi-ammom- z CHz-S(O)z-CH3carboxylic acid O-JVZ lVriz tm :riz-l:ry-~riz-l:ri,-u-pnenyi-ammom- z CHz-S(O)z-CH3carboxylic acid O-JVZ-Nriz rl 1a12-l:ril-1;ri2-n- -p eny -ammo m-CHz-S(O)z-CH3carboxylic acid o- Uz-NHz H CHz-CH(-CHz-a y p enoxy-aceticm- z CHz-S(O)z-CH3acid ester o- z- z H CHz-CH(-CHza y -p enoxyaceticm- z CHz-S(O)z-CH3acid ester o- z- z - ~ CHz-CH(-CHz-a y -p enoxy- m- z - acetic CHz-S(O)z-CH3acid ester o-SVZ-NriZ z- z- a y 3-p enoxy- m- z CHz-S(O)z-CH3acetic acid ester o-5Uz NHz H Ltiz-fail-laiz-Memyi l:ri3-u-pnenoxy-m-~l=r~ry~riz CHz-S(O)z-CH3acetic acid ester o-~uz-NHz ti l:riz-l:ril-l:riZMemyi rsn-u-pnenoxym- z CHz-S(O)z-CH3acetic acid ester o ~z-NHz H CHz-CH(-CHZMethyl Yhenoxyaceticm-C:(=U)NHz CHz-S(O)z-CH3acid ester o- z- 2 H CHz CH(-CHz-Methyl Cl-phenoxyaceticm-(:(=U)NHz CHz-S(O)z acid ester o- Z z H CHz-CH(-CHz-Methyl l'-phenoxyacehcm-(:(=U)NHz CHz S(O)z-CH3acid ester o-JVZ-NriZ H caiz-fail-laiznnemymai3-pnenoxy-m-l.l=u~~tiz CHz-S(O)z-CH3acetic acid ester o-JUZ-NHz H 1;t12-l:ril-1;ri2-mecnyll~ri3-u-prienoxym-l:l=VJ1Vr12 CHz-S(O)z-CH3acetic acid ester O-JU2-NH2 ti caiz lail-laiz-nnecnyi tsn-u-pnenoxym- z CHz-S(O)z-CH3acetic acid ester o-SOz-NHz H CHZ CH(-CHz-Yhenoxyacehc m- z acid CHz-S(O)z o- z-NH2- H z z- -p enoxy-acetic m- z - aci CHz-S(O)z-CH3 o- z-NHz H z- Z -p enoxy- aceticm- z aci CHz-S(O)z-CH3 o- Uz-NHz H CHz-CH(-CHz-CH3-phenoxy-acericm- z acid CHz-S(O)z-CH3 o- z-NHz H CHz-CH(-CHz-CH3-U-phenoxy-aceticm- z CHz-S(O)z-CH3acid o-SOz NHz H CHz-CH(-CHz-n- -p enoxy aceticm- z aci CHz-S(O)z-CH3 o-SOz-NHz H CHz-CH(-CHz-Yhenoxyacetic m- z acid CHz S(O)z-CH3 o-SOZ NHz H CHz-CH(-CHz-Cl-phenoxyaceticm-(:(=U)NHz acid CHz-S(O)z-CH3 o-SOz-NHz H CHz-CH(-CHz-1-phenoxyacetic m-C(=U)NHz acid CHz-S(O)z-CHj o-SOz-NHz H CHz CH(-CHz-CH3-phenoxy-aceticm-C:(=U)NHz acid CHz-S(O)z-CH3 o-SOz-NHz H CHz-CH(-CHz-CH3-U-phenoxy m-C(=U)NHz acetic CHz-S(O)z-CH3acid o-SOz NHz H CHz-CH(-CHz-tan-U-phenoxy m-C:(=U)NHz acetic acid CHz-S(O)z-CH3 o-z- z z- z- enoxye iano .~ ....~...
m-CHz-S(O)z-CH3 o-z- z z- z- -p m~)~z enoxy-a ano ,.,.
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u.
CHz-S(O)z-CH3 O-JUz-Ntiz ti ~riz-~ry-~;tizr-pnenoxy- m-~~=ivryNriz emanoi CHz-S(O)z-CH, o-JVz-Nriz t~ ~riz-Lti(-utiz-t;ti3-pnenoxy-emanoi m-~~=NriJNriz CHz-S(O)z-CHj O-JUz-Nriz t~ uriz-uty-urtz-uti3-u-pnenoxy-emanoi m-u~=NryNriz CHz-S(O)Z
CH, o-~uz-Ntiz ri urtz-ur1(-uriz-~sn-u-pnenoxy m-~(=mryNriz emanoi CHz-S(O)z-CH3 o-~uz-Nriz ti ~riz ~ry-~ry-enoxye m- z ano CHZ S(O)z-CH3 o-~uz-Nttz ti ~riz-pry-~riZm-pnenoxyemanoi m- z CHz S(O)z-CH3 o-~uz-Ntiz t1 t_:rizw;tll-~;tlzr-pnenoxy-etnanoi m- z CHz S(O)z-CH3 O-JUz-Ntiz ri l:riz-l:ri(-l;riz-3-p m- z enOXy-a ano CHz-S(O)z-CH3 o-~Uz-Ntiz ti z- z- 3- m- z _p enoxy-a ano CHz-S(O)z-CH3 O-~Uz-Nriz z- z- n- m- z -p enoxy-a ano CHz-S(O)z-CH3 o-auz-Ntiz m ;tiz ~;ti~-~:riz-nnewyi m-~.~=mriyvriz pnenoxy-emyi CHz-S(O)z-CH3ether o-JVz-Nriz t1 Ltiz-~;ti(-caiz-nnetnym;i-pnenoxyemyi m-~:~=mryvriz CHz-S(O)z-CH3ether o-JVZ tlz ti Ltiz-~ai~-~;tiz-a m- z N y -p enoxy-a y CHz-S(O)z-CH3ether o-~u2 riz ti l:riz-~;ti(-lJriz-Memym;ti3-pnenoxy- m- z N
CHz-S(O)z-CH3ethyl ether O-~Uz-Ntiz ti Lti2 Lti(-caiz-Metnyi m- z ~ri3-u-pnenoxy-CHz-S(O)z-CH3ethyl ether O-JUz-NHZ H Calz-lal(-1:ri2-rnetnyi m- z rsn-u-pnenoxy CHZ S(O)z-CH3ethyl ether O-JUz-Ntlz ti ~riz-~ry-~riz-Memyi m-~,~=a rnenoxyemyi yvriz CHz-S(O)z-CH3ether O-~uz-Nriz ti Ltiz-pat(-~aiz-nnemymu-pnenoxyerrryi m-~:~=uyvriz CHz-S(O)z-CH3ether o-~u2 tlz tm aiz-~;ti(-~aiz-nnetnyi m- z N r-pnenoxyetnyi CHz-S(O)z-CH3ether o-JUz-Ntlz t1 lalz-l;tl(-l:rlz-MeTriy1 m-~;r13=
CHz-S(O)z-CH3 phenoxyethyl ether o-JUz-Nt12 ti laiz-1:r1(-taiz- nnemyi ~n3-u- m- z CHz-S(O)z phenoxyethyl CH, ether O-JVz-Nriz ti l:riz l=rl(-1;ri2- a y n- m- z ~
CHz-S(O)z-CHjphenoxyethyl ether o-JUz-Nriz t1 caiz-~;ti(-~;tiz-pneny m-~:~=mryvriz hexane)-o-~u2 tiz ti z- z- -p m- z N eny hexane)-O-~Uz-Nriz ti ~tiz-~ri~-~riz-r-pnenyi m-~~=Nriyvriz hexane)-o-JUZ-Nri2 t1 l:rlz-~;tt(-~atz-3-p m- z eny hexane)-o-~uz-Ntiz t~ trtiz ~ti~-~tiz-~;ri3-u-pnenyi m-~.~=mryvriz hexane)-O-~uz-Nriz n taiz-pry-~ri2-tsn-u-pneny m-~~=ivryvriz hexane)-o-~uz-Nriz ti ~riz-~ti~-~tiz-pnenyi m-~~=u~Nriz hexane)-o- z- z z- z- -p eny m_ v~ v~a.a hexane)-o_ z_ z - z_ z_ -p eny m-C( O)NHz .. . ..
hexane)-O-JVz-NHz ri l:riz-l:ri(-l:riz-c:ri3-pnenyi m-~(=u~wriz hexane)-O-JVZ-NriZ ri I:HZ l;H(-l:Hz-C;H3-u-prienyl m-hexane)-O-JUz-Nriz ri l:riz-l:ri(-l:nz-n- -p eny m- z hexane)-o-~uz-NHz ti lain lai(-litiz-me p-hexane)-o-~uz-NHz n z z- -am me p- z hexane)-O-lu2-NHZ ti lalZ l;tl(-lain-r-allllllle p-l.(=lVr1)1V112 hexane)-O-JUZ-NHz H l:Hz-liri(-1x12-1,ri3-anlllIle p-l;(=1Vri)Nriz hexane)-o-~uz-NHz ri l:riz-l:ri(-~riZl:ri3-u-anume p- z .
hexane)-O-JUz NHZ H l:Hz-l:H(-l:Hz-tSn-u-amlme p-hexane)-O-JV2-NHZ H l:Hz l:H(-C;HZ-m Ille p-hexane)-O-JUZ-NHZ H 1:H2-C;H(-l:riZ-l;l-anllme p-hexane)-o-JVz-Nriz H z- z- -am me p- z hexane)-o-~Vz-NHz H l:Hz-c:H(-~riz-l:ri3 amtme p-1:(=u~~riz hexane)-o-5Uz-NHz H z- z_ 3_ -ant me p- z hexane)-O-JUZ-NHZ H l;Hz l:H(-1:H2-tan-u-anllme p-l:(=V)lVriy hexane)-o-~Vz-NHz H z- z- eny -ammo-car m- z oxy is hexane)- acid o-JVz-NHZ H 1:H2-l;H(-C;HZ-l:l-Yrienyl-amlIlom-l:(=LVri)iVriz , hexane)- carboxylic acid o-JVZ NHz H MHz-1:H(-l:Hz-r-pnenyi-ammo m-1:(=wrywriz hexane)- carboxylic acid o-JVZ-NHZ H l;Hz-l;H(-liriz_1x13-prienyl-ammom-l.;(=lVriJ1vt12 hexane)- carboxylic acid O-5Vz-NHZ H I:HZ l;H(-I:HZ-1;ri3-u-prieriylm-l;(=iVtl)lvrlz ammo hexane)- carboxylic acid o-5uz-NHz H l:Hz-1;H(-llHz-tsn-u-pnenyi m-1:(=Nryvriz ammo hexane)- carboxylic acid o-~uz-NHz H l:Hz-l:ri(-l:riz-rnenyi-ammo carnoxyncm-1:(=l.r~wriz hexane)- acid o-aVz-NHz H ~riz-l:ri(-~rizla-pnenyi-ammo m- z hexane)- carboxylic acid o-~uz-NHz H l:riz-l:ri(-l:riz-r-pnenyi-ammo m- z hexane)- carboxylic acid o-aVz-NHz H l:riz-l:ri(-l:Hz-l:ri3-pnenyi-ammom-1:(=u)rrriz hexane)- carboxylic acid o-~uz-Ntiz H l:riz-1:H(-c:Hz-l:ri,-u-pnenyi-ammom- z hexane)- carboxylic acid o-~uz-NHz H ~riz-c:ri(-l:Hz-tsn-u-pnenyi-ammom-1:(=u~wriz hexane)- carboxylic acid o-SOz-NHz H (:Hz-(:H(-C;Hz-Methyl phenoxy-aceticm-C;(=NH)NHz hexane)- acid ester o-SOZ NHz H CHz-CH(-(:Hz-Methyl (:1-phenoxyacehcm- z hexane)- acid ester li-J
o- r z z- r et y -p enoxy- m- z acetic hexane)- acid ester O-JV2-Nri2 tt y aiz-Ltil-Ltiz-nnemymai3-pnenoxy-m-t,l=~rywriz hexane)- acetic acid ester O-JUz-Ntiz ri t,riz aril-~riz-nnemymai3-v-pnenoxy-m-~l=r~ryvriz hexane)- acetic acid ester O-JV2-Ntl2 m ;ttZ tail-~riz-a y n- -p enoxy m- z hexane)- acetic acid ester o-SOz-NHZ H CHz-CH(-CHz-Methyl Phenoxyacehcm- =U z hexane)- acid ester o-SOz~ H CHz-CH(-CHz-a y -p enoxyacehcm- =U z hexane)- acid ester o-SOz-NHz H z- z- a y -p enoxyacehcm- z hexane)- acid ester O-JUZ NHz t~ ~riz-~til-~tiz-nnemym;ri,-pnenoxy-m-~l=~~~riz hexane)- acetic acid ester o-~uz Nri2 m aiz-~ayuaiz-Metnyi t.ti3-v-pnenoxym- z hexane)- acetic acid ester O-JUz Nriz ri ~riz-~ry-~rizmewyi rsn-u-pnenoxym- z hexane)- acetic acid ester o-~Oz-NHZ H CHz-CH(-CHz-Yhenoxyaceric m-(:(=NH)NHz acid hexane)-o-SOz-NHz H CHz CH(-CHz-Cl-phenoxy-aceticm- z acid hexane)-o-SOz-NHz H CHz-CH(-CHz-1~'-phenoxy- m-(:(=NH)NHz acetic acid hexane)-o-SOZ-NHz H CHz-CH(-CHZCH3-phenoxy-aceticm- z acid hexane)-o-SOz-NHz H CHz-CH(-CHz-CH3-U-phenoxy-aceticm-C:(=NH)NHz hexane)- acid o- Oz-NHz H CHZ CH(-CHz-Bn-U-phenoxy m-C(=NH)NHz acetic acid hexane)-o-SOz-NHz H Z z- enoxyacehc aci m- z hexane)-o- UZ~TH2 H z- z- -p enoxyacehc m- z -- aci J
hexane)-o- Oz-NHz H CHz-CH(-CHz-F-phenoxyacehc m-C;(=U)NHz acid hexane)-o-SOz-NHz H r r 3-p enoxy-aceticm- z aci hexane)-o-SO~THz H z- r 3- -p enoxy acericm- z hexane)- acid o- ~lHz H CHz-CH(-CHZtan-U-phenoxy m-(:(=U)NHz acetic acid hexane)-o-~uz-Nriz ti ~nz-~ril-~nz-enoxye ano m- z hexane)-o-~uz-Nttz 11 l:rizW :rilW:rtz~:1-pnenoxy-emanolm- z hexane)-O-JVz-Nriz z- i -p enoxy- a ano m- z hexane)-o-~u2 Ntiz t~ qty-~ry-~ry-iris-Pnenoxy-ecnanoim-~l=~ryr~riz hexane)-o-~uz-Ntiz t~ Ltiz-~til-~riz-~ri3 u-pnenoxy-emanoim-~l=~ryr~riz hexane)-o-~uz-Ntiz t~ ~tiz-~ry-~riz-tsn-u-pnenoxy m- z emanoi hexane)-O-JVZ-Ntlz n ~-rir~-ril-~-riz-YneriOXyeinan0l m-hexane)-o-~uz Ntiz ti ~tiz-~ry-~rtz-m-pnenoxyemanoi m-~l=~~mriz hexane)-o-~uz-Ntiz m ay--ry-t-riz-r-pnenoxy-emanoim-~:l=~~mriz hexane)-o-z- z H m-C(=O)NHz v11 vllt-VllVll z- z- 11 3-p enoxy-et anol hexane)-O-JUz-Nriz ri ~;riz-t:ril-taiz-Lti3-u-pnenoxy- m-t:l=u)ivriz emanoi hexane)-O-JUZ-wriz ri ~riz-~:ril-taiz-tsn-u-pnenoxy- m-t_;l=u)wtiz emanoi hexane)-O-JUZ-wriz ri ~:riz-aril-taiz-Metnyi m-t:l=ivti)ivtiz pnenoxy-emyi hexane)- ether O-JVZ tiz rm _;riz-aril-~tiz-Memyi m-ul=ivri)Nriz N ta-pnenoxyemyi hexane)- ether O-JU2-lVriz Lriz-~-ril-Lriz-Memyi m-~:l=ivri)Nriz r-pnenoxy-emyi hexane)- ether O-JUZ-Ntiz z- z- a m- z y ,-p enoxy-hexane)- ethyl ether O-JUz-Nriz ri ~;riz-tail-t:rizMemyi m-t:l=ivri)ivriz ~ri3-v-pnenoxy-hexane)- ethyl ether o-JUz-iVriz z- z- a m- z y n--p enoxy hexane)- ethyl ether o-SOz-NHz z- z- a m- z y enoxyet y hexane)- ether O-JUz-lVriz ri ~-riz-~-ril-t-riz-Metnyi m-~:l=u)Nriz ta-pnenoxyemyi hexane)- ether O-JUz-Ntiz ri caiz-aril-~riz-a m- z y -p enoxye y hexane)- ether O-JUz-Ntlz r1 t:riz-fall-1;ri2-lVlelllyi m- z 1;ri3-hexane)- phenoxyethyl ether O-JUz-Nriz ri lalz-l:ril-1:ri2- MeTllyi l;rij-u-m-l:l=u)lVriz hexane)- phenoxyethyl ether o-au2 tiz rm ;riz-~;nl-t:ri2 memyi rsn-u- m-~l=u)rVriz iv hexane)- phenoxyethyl ether o-~uz-Nriz ri t:riz-t.ril-uriz-pnenyi m-~l=ivri)ivriz (HO-phenyl))-o-~uz-mtiz ti taiz-~atl-~aiz_-p m- z eny (HO-phenyl))-o-~uz-Ntiz t~ t:riz-t:rilw:riz-r-pnenyi m-~.l=mri)mriz (HO-phenyl))-o-~uz-lVtiz ti taiz-Ltil-taiz-Lti3-pnenyi m-t:l=ivri)wtiz (HO-phenyl))-o-~uz-Ntiz z- r s- m- z -p eny (HO-phenyl))-o-~u2 riz ri taiz-~;til-Ltiz-tsn-u-pnenyi m-t:l=ivri)ivriz N
(HO-phenyl))-o-~uz-wiiz n z z- p m- z eny (HO-phenyl))-O-JUz-ivriz ri taiz-~:ril-t:riz-ta-pnenyi m-~,l=u)ivriz (HO-phenyl))-O-JUz-Nriz ti z- z -p m- z eny (HO-phenyl))--o-z- z z- z_ 3-p m-C(=O)~z eny W
(HO-phenyl))-o-~uz riz m aiz-~:ril-~riz~:ri3-u-pnenyi m-~.l=u)ivriz iv (HO-phenyl))-o-~uz-ivtiz ti t:riz-t:ril-t:riz-tsn-u-pnenyi m-t.l=u)ivriz (HO-phenyl))-O-JUZ-ivriz ri ~:riz-~:ril-t.riz-Amime p-t.l=ivri)ivriz (HO-phenyl))-o-~uz-ivriz ti ~tiz-tail-t:riz-la-anume p-t:l=rrri)ivriz (HO-phenyl))-o-~uz tiz m ;riz-aril-~riz-r-amime p-t:l=rrri)ivriz N
(HO-phenyl))-o-~uz-Ntiz r~ ~nz-aril-~riz-t:ri3-anume p-~l=rVri)ivnz (HO-phenyl))-n- z- z z- r s--am ..~ .,..,.,.
me p-(HO-phenyl))-c- r z z- z- n- p- NHz -am ._,~ .,.., me (HO-phenyl))-O-JUZ-NHZ H l;Hz-l:H(-l:HzAnllme p-l:(=U)Nriz (HO-phenyl))-o-JUZ-NHZ z- z- -ant p-me (HO-phenyl))-o-JVz NHz H c:Hz-1;H(-l;rlz-r-anllme p-~:(=v)Nrtz (HO-phenyl))-O-JUz-NHZ H l:HZ-l;tl(-l;Hz-1;H3-anllme p-(HO-phenyl))-O-JUz-Nriz ri l.;rlz-l;ti(-l;riz-1x13-u-anllme p- z (HO-phenyl))-O-JUZ-NHZ ti 1:H2-l:H(-1;r12-tsn-v-anllme p-L(=V)1vr12 (HO-phenyl))-o-5U2 NHz H 1;H2 1:H(-l:HZ-rnenyl-ammo-carnoxync m-1:(=Nri)Nriz (HO-phenyl))-acid o-~uz-NHz H l:HZ-1.;H(-l:HZ-1:1-rnenyl-ammo m-~;(=lvri)lvriz (HO-phenyl))-carboxylic acid o-JVz-Nriz H l;tiz-~H(-l:HZ-r-phenyl-ammo m- z (HO-phenyl))-carboxylic acid o-5Uz-NHZ H 1:H2-l;H(-1;t12-1x13-phenyl-ammo m-(HO-phenyl))-carboxylic acid o-5Uy-NHZ H 1:H2-l:H(-l:Hz~-t13-U-phenyl m-ammo (HO-phenyl))-carboxylic acid o-5U2-NHZ H C;Hy-l;H(-1x12-tsn-u-phenyl m- z ammo (HO-phenyl))-carboxylic acid o-SUz NHz H t;Hz-1:H(-l:HZ-rnenyl-ammo m- z cardoxync (HO-phenyl))-acid O-SVz-NHz H C:HZ-liH(-l:Hz_-p y -ammo m- y eri (HO-phenyl))-carboxylic acid o-SUZ-NHZ H C:riz-l;ri(-1:H2-r-phenyl-ammo m- z (HO-phenyl))-carboxylic acid o-~Uz-NHz H c:H2l:H(-c:Hz-l:rt3-phenyl-ammo m-1:(=l.r)wriz (HO-phenyl))-carboxylic acid O-JUz-NHZ H C:HZ-l:H(-l:Hz1;ri3-U-phenyl-ammo m-l:(=V)lVriz (HO-phenyl))-carboxylic acid o-JUz-NHz H l:Hz-1;H(-l:rlztsn-u-phenyl-ammo m-1:(=v)lvriz (HO-phenyl))-carboxylic acid o-SOz-NHz H CHz-CH(-CHz-Methyl m- z phenoxy-acetic (HO-phenyl))-acid ester o-SOz-NHz H CHz-CH(-CHz-Methyl m-C(=NH)NHz Cl-phenoxyacehc (HO-phenyl))-acid ester o- z- z H CHz-CH(-CHz-Methyl m- z F-phenoxy-acetic (HO-phenyl))-acid ester O-5U2 NHZ H C:riz-l:ri(-1:ri2-rnemyl m- z l:Hj-pnenoxy-(HO-phenyl))-acetic acid ester o-5uz-NHz H LHz-l;ti(-l:HZ-a m- z y -p enoxy-(HO-phenyl))-acetic acid ester O-JVZ-NHZ H C:Hz l;ri(-l:Hy-MeLllyl m- y tin-U-prienOXy (HO-phenyl))-acetic acid ester o-SOz-NHz H CHz-CH(-C;Hz-Methyl m- z Yhenoxyacehc (HO-phenyl))-acid ester o- OZ-NHZ H CHz-CH(-CHz-Methyl m- z Cl-phenoxyacehc (HO-phenyl))-acid ester o-SOz-NH2 H CHz-CH(-CHz-Methyl m-C(=U)NHz l~'-phenoxyacehc (HO-phenyl))-acid ester o-JUZ-NHZ t1 I:HZ-l;H(-1:H2-MeTClyll:rig-prieriOXy- m-L(=V)lvri2 (HO-phenyl))-acetic acid ester O-JUy-NHZ H l:HZ l.H(-1:H2-1\nemyl m-1:(=u)lvriz l:ri3-v-pnenoxy (HO-phenyl))-acetic acid ester o- - - ~ a y n_ _p enoxy m=C(~jNHz VV 111 11 v11 ~r11~-v111Y1 Lll 117 V
(HO-phenyl))-acetic acid ester o-5Vz-NHz H C:Hz-C:H(-C;Hz-Yhenoxyacehc m-C:(=NH)NHz acid (HO-phenyl))-o-SUz-NHz H C;Hz-(:H(-C;Hz-C;1-phenoxy-acericm- z acid (HO-phenyl))-o-SOz-NHz z- r -p enoxy- aceticm- z aci (HO-phenyl))-o-SOz-NHz H C:Hz-C;H(-CHz-C;H3-phenoxy-aceticm-(:(=NH)NHz acid (HO-phenyl))-o-SOz-NHz H (:Hz-C;H(-C;Hz-j- -p enoxy-aceticm- z (HO-phenyl))-acid o- z- z z- z- n- -p enoxy aceticm- z aci (HO-phenyl))-o-SOZ NHz H (:HZ (:H(-C:Hz-Yhenoxyacehc m-C;(=U)NHz acid (HO-phenyl))-o-SUz-NHz H C:Hz-C;H(-LHz-C;1-phenoxyacehcm-C;(=U)NHz acid (HO-phenyl))-o-SUz-NHz H C;Hz-(:H(-(:Hz-r~-phenoxyaceticm-C:(=U)NHz acid (HO-phenyl))-o-SOZ NHz H C;Hz-(:H(-C:Hz-(:H3-phenoxy-aceticm-(:(=U)NHz acid (HO-phenyl))-o-SOz-NHz H (:Hz-(:H(-C;Hz-C:H3 U=phenoxy m-(:(=U)NHz acetic (HO-phenyl))-acid o- z- z r z- n- -p enoxy aceticm- z aci (HO-phenyl))-O-JVZ-NHz tl lal2-fall-l,tlZ-YnenOXyeLIlan01 m-l,l=ivtlJlVtlz (HO-phenyl))-o-~uz NHz H l:Hz-l:til-~aiz-1:1-pnenoxy-emanoim-l:l=ivttlivtiz (HO-phenyl))-o-JVZ-NHZ t1 ;rizW;til-l~ti2-t'-prienOXy- m-eTtlanoi (HO-phenyl))-o-5Vz NHz r r 3-p enoxy-a ano m- z (HO-phenyl))-o-~uz-NHz z- z- 3 -p enoxy-a m- z ano (HO-phenyl))-O-JVz-Nriz H l:Hz l:Hl-l:riz-tsn-u-pnenoxy m-l:l=ivryivtiz emanoi (HO-phenyl))-o-~uz-mtiz ti z- z- enoxye ano m- z (HO-phenyl))-O-JVZ-Nriz z- z- -p enoxye ano m- z (HO-phenyl))-O-JV2 NHZ H Cain-l:H(-1;H2-r-pnenoxy-emanoim-l:l=uJivriz (HO-phenyl))-o-~uz-mtiz ti lain lail-laiz-lai3-pnenoxy-emanoim-l;l=~~ivriz (HO-phenyl))-o-~uz-NHz H ~riz-~ril-~riz-~n3-~-Pnenoxy- m- z emanoi (HO-phenyl))-O-JUZ-NHz H l;Hz-Gail-Cain-tin-V-pneriOXy- m-l:l=u)iVtlz elllanoi (HO-phenyl))-o-auz-NHz H laiz-l:ril-~riz-iviemyi pnenoxy-emyim-l;l=mri~wriz (HO-phenyl))-ether o-~uz-Ntiz ti laiz-l,til-l:riz-iviemyi la-pnenoxyetnyim-l:l=ivryivriz (HO-phenyl))-ether o-~uz Ntiz ti ~riz-~-nl-~riz-iviemyi r-pnenoxy-ecnyim-l:l=ivri~wry (HO-phenyl))-ether o-~uz NHz H LHz-l,ril-l:riz-iviemyi pry-pnenoxy-m-l:l=ivryvriz (HO-phenyl))-ethyl ether O-JUz-lVri2 t1 1x12-fail-Cal2-nnemyi ~i-y-u-pnenoxy-m-l:l=ivriyvriz (HO-phenyl))-ethyl ether O-JVZ NHy H 1.H2-lail-l;riZ-Meinyi ISn-u-pnenOXym-(HO-phenyl))-ethyl ether o-z- z z- z- et m- z y enoxye y (HO-phenyl))-ether o-JVz-Nriz t~ ~riz-Ltil-~riz-Merry m- z Li-pnenoxyemyi (HO-phenyl))-ether O-JVz-NHz t~ ~riz-~ti(-c:riz-Merry m- z r-pnenoxyemyi (HO-phenyl))-ether o-5Uz-Ntlz H 1;t12-l;H(-l;tlz-Mettlyl m- z C;ri3-(HO-phenyl))- phenoxyethyl ether o-5u2 tiz ri c:tiz ~t1(-~tlz- Metnyi Lti3-u- m-~~=u~Nriz N
(HO-phenyl))- phenoxyethyl ether o-5Vz tiz ti lalz l;H(-l;tlz- Melllyl tSn-u- m- z N
(HO-phenyl))-phenoxyethyl ether o-5Vz-Ntlz t1 z- z- p m- z eny (Cl-phenyl))-O-JVZ tlz ti Calz-lal(-lalz-l;l-pnenyl m-l:(=lVt1)lVtlz N
(Cl-phenyl))-O-5Vz-Ntiz ti 1:112-lat(-laiz-r-prienyl m-(Cl-phenyl))-o-5uz-Ntiz ti c:riz-l:ri(-l,riz-~;tt3-pnenyi m- z (Cl-phenyl))-o-5uz t-iz tm :riz-pry-~riz~rij-u-pnenyi m- z N
(Cl-phenyl))-O-5Vz-Ntlz ti l;tlz-lal(-l;tiz-t5n-V-prienyl m- z (Cl-phenyl))-o-JUz-Nriz ti laiz-l:ri(-l.:riz-p m- z eny (Cl-phenyl))-o-JUZ-Nriz ti laiz-Lti(-l,tiz_-p m- z eny (Cl-phenyl))-O-SUz-Nriz ti c;tiz c:ri~-~riz-r-pnenyi m-~~=u~wriz (Cl-phenyl))-O-JVZ t12 H 1;t12-lal(-l:riy-~ri3-pnenyi m- z N
(Cl-phenyl))-o-~uz-Ntlz ti ~alz-Lt1(-Lrlz~;tlj-urpnenyi m- z (Cl-phenyl))-O-JU2-Ntiz n ~riz-pry-~riznn-u-pnenyi m- z (Cl-phenyl))-o-au2 riz ri l:riz-l:ri(-l:riz-Amime p- z N
(Cl-phenyl))-o-JUz-Nriz ti laiz-la1(-latz--am p- z 1ne (Cl-phenyl))-o-SVZ tiz z z- -am p- z N me (Cl-phenyl))-o-JVz-Nri2 ti l:riz lay(-~;t~z-~at3-am~me p-~:~=Nti~ruriz (Cl-phenyl))-O-JVz-Nriz ri c:riz-lairc:riz-3- p- z -am me (Cl-phenyl))-O-JUz-Nri2 n z- z n- p- z -ant me (Cl-phenyl))-o-z z z- z- m p- z me (Cl-phenyl))-o-~uz-Nrtz ti c:nz t_;ty-~riz-m-amime p-~~=u~~riz (Cl-phenyl))-O-JVZ-Ntiz ti 1x12-litl(-lalz-r-amlllle p-L(=V)lVriz (Cl-phenyl))-o-~uz-Nriz m :riz-pry-~tiz-~ri3-amnne p-~~=u~r~riz (Cl-phenyl))-O-JVZ riz m :riz-~ri~-~riz-~ri3-u-amime p-~~=u~r~riz N
(Cl-phenyl))-o-~uz-Ntiz rm :riz-pry-~riz-nn-v-amime p-~~=u~mriz .
(Cl-phenyl))-O-JVz-Nriz rm ;riz-pry-~riz-rnenyi-ammo-carooxyiic m- z (Cl-phenyl))-acid o- z z z- z- eny -ammo m- (=NH)NHz w.m a a v (C1-phenyl))-carboxylic acid o-5uz-NHz H c:Hz-l:Hl-t;Hz-r-pnenyi-ammo m-~:(=mry~riz (Cl-phenyl))-carboxylic acid o-SUz NHz H c.;Hz-t;H(-l:Hz-c:H3-pnenyi-armnom-l:l=NtyNriz (Cl-phenyl))-carboxylic acid o-JVz-NHz H ~riz-~Hy:Hz1:H3-u-pnenyi m-l:l=~ryr~ry ammo (Cl-phenyl))-carboxylic acid O-JV2-NHz H l:riz-l:ril-c:Hz-nn-v-pnenyi ammom-~(=~ryr~riz (Cl-phenyl))-carboxylic acid o-5uz NHz H l:Hz-l:Hl-c:Hz-rneny-ammo carnoxyncm-l:l=v~Nri2 (Cl-phenyl))-acid o-JV2-NHz H l:Hz-l:Hl-laiz-la-pnenyi-ammo m- z (CI-phenyl))-carboxylic acid o-~uz NHz H l:Hz-t;Hl-c:riz-r-pnenyi-ammo m-l:l=~Jmriz (Cl-phenyl))-carboxylic acid o-~uz NHz H l:riz-l:ril-l:riz-~ri3 pneny-ammo m-~(=lywriz (Cl-phenyl))-carboxylic acid O-JUZ-NHz H l:riz-l:ril-l:riz-~ri3-v-pnenyi-ammom-~(=v~~riz (Cl-phenyl))-carboxylic acid o-SUZ NHz H l:Hz-c:Hl-l:Hz-tsn-u-pnenyi-ammom- z (Cl-phenyl))-carboxylic acid o- Z z H CHZ CH(-CHz-Methyl phenoxy-aceticm- z (Cl-phenyl))-acid ester o- z- z - H CHz CH(-CHz-a y -p enoxyacehcm- z (Cl-phenyl))-acid ester o- z- z H CHz CH(-CHz-a y -p epoxy- m- z acetic (Cl-phenyl))-acid ester o-JVZ NHz H 1;H2-l:ril-1:ri2-metnyi lai3-pnenoxy-m- z (Cl-phenyl))-acetic acid ester o-5uz-NHz H 1:HZ l:Hl-l:Hz-Metnyi l:ri3 m- z u-pnenoxy-(Cl-phenyl))-acetic acid ester o-5U~ NHz H ~:Hz-c:Hl-c:H2-Metnyi tsn-u-pnenoxym- z (Cl-phenyl))-acetic acid ester o-SOz-IVHz H CHz-CH(-CHz-Methyl Yhenoxyacehcm- z (Cl-phenyl))-acid ester o- z- z H CHz-CH(-CHz-Methyl Cl-phenoxyacericm- z (Cl-phenyl))-acid ester o- Oz-NHz H CHz-CH(-CHz-Methyl r~-phenoxyacehcm- z (Cl-phenyl))-acid ester O-JUZ-Nriz H l:Hz-lail-l:riz-Memyi lai3-pnenoxy-m- z (Cl-phenyl))-aceric acid ester O-5Uz-NHi H l:Hz C.:HI-1;H2-lVlemy11x13 u-pnenOXym-(Cl-phenyl))-acetic acid ester o-5uz-NHz H c:Hz-l:Hl-LHZ-Metnyi tsn-u-pnenoxym- z (Cl-phenyl))-acetic acid ester o-SOz-NHz H z- z- enoxyacehc aci m- z (Cl-phenyl))-o- Oz-NHz H CHz-CH(-CHZCl-phenoxy-aceticm-C(=NH)NHz acid (Cl-phenyl))-o-SOz-NHz H CHz-CH(-CHz-F-phenoxy- aceticm- z acid (Cl-phenyl))-o- Oz-NHz H CHz-CH(-CHz-CH3-phenoxy-aceticm- z acid (Cl-phenyl))-o-SOz-NHz H r r s- -p epoxy-aceticm- z (Cl-phenyl))-acid o-SUz-NHz H CHZ CH(-CHz-tan-U-phenoxy m-C(=NH)NHz acetic acid (CI-phenyl))-o-SOz-NHz H CHz-CH(-CHz-Yhenoxyacehc m-C(=U)NHz acid (Cl-phenyl))-o-SOz-NHz H CHz-CH(-CHz-Cl-phenoxyacehc m-C(=U)NHz acid (Cl-phenyl))--o- z- z r r -p enoxyacehc .., ...,...
acl m- z (Cl-phenyl))-o- z- z z- z- ,-p enoxy-aceticm-C(=O)NHZ
acl (Cl-phenyl))-- - z ~ CHz-~z -- ~~_O=p~noxy aceticm-C(=U)NHz (Cl-phenyl))-acid o- z- z H CHz-CH(-CHz-n- -p enoxy aceticm- z acl (Cl-phenyl))-o-SUz-NHz H z- - z- enoxye ano m- z (Cl-phenyl))-o-5Uz NHz H ~%HrLHI-Lriz-Ll-pnenoxy-emanolm- z (Cl-phenyl))-o-SU2 NHz H ~;HZ-c:Hl-~:Hz-r-pnenoxy- emanolm- z (Cl-phenyl))-O-SUy-NHy H 1:r12-(:Hl-1:H21;H3-prienoxY-elllariolm-(Cl-phenyl))-O-JUz-NHZ H lalZ-l;tll-l:riz-~ri3-V-pnenoxy-emanolm-~:l=mri)~riz (Cl-phenyl))-o-5Uz-NHz H LHz-LHl-LHz-~n-u-pnenoxy m- z emanol (Cl-phenyl))-o-5Uz-NHz H c:Hz-uHl-LHZrnenoxyemanol m-~l=v)wriz (Cl-phenyl))-o-JUZ-Nri2 H Lriz-Lnl-Lnr~l-pnenoxyemanoim- z (Cl-phenyl))-O-5u2-NHZ H 1:H2-l;Hl-l;Hzr-prienoxY-ethanolm-(Cl-phenyl))-o-5Uz-Nriz H z- z- 3-p enoxy-a ano m- z (Cl-phenyl))-o-5Uz-NHz H z- z- 3- -p enoxy- m- z a ano (Cl-phenyl))-o-5Vz-NHz H Lriz-LHl-LHztsn-u-pnenoxy- m-~;l=u)lrrlz ethanol (Cl-phenyl))-o-5U2 NHz H LHz-LHl-calz-a Y p enoxy-a m- z y (Cl-phenyl))=ether o-SUz-NHz H (:Hz-C:HI-c:Hz-a y -p enoxye m- z y (Cl-phenyl))-ether o-SUz NHZ H (:HZ-LHl-c:H2-a y -p enoxy-a m- z y (Cl-phenyl))-ether o-SUZ-Nriz H LHz-LHl-c:Hz-lvieulyl ~H3-pnenoxy-m- z (Cl-phenyl))-ethyl ether o-5uz-NHz t1 :Hz-t;Hl-Ltiz-lvietnyl ~tlj-u-pnenoxy-m-~l=lrri)lrrlz (Cl-phenyl))-ethyl ether o-~Uz-NHz ti uHz-c:ry-~rlz-lvietnyl nn-v-pnenoxym- z (Cl-phenyl))-ethyl ether o-JVz-NHz ti MHz-~tll-~lnz-mlemyl rnenoxyemylm-~l=u)mriz (Cl-phenyl))-ether o-SOz-NHz H CHz CH(-CHz-Methyl Cl-phenoxyethylm- z (Cl-phenyl))-ether o-~u2-NHz H (aiz-~:Hl-Ltiz-lvlemyl r-pnenoxyetnylm- z (Cl-phenyl))-ether o-JVZ-NHZ H (a12-l;Hl-1;H2-MeLllYll;ri3- m-l;l=u)lVrlz (Cl-phenyl))-phenoxyethyl ether o-JVZ NH2 H 1;H2-fall-l;tlz-MeTllYl 1x13-v- m-(Cl-phenyl))-phenoxyethyl ether o-~uz-NHz H ~tlz-c:rll-c:riz-a y n- m- z (Cl-phenyl))=phenoxyethyl ether o-~u2-Ntlz ti MHz-~rll-c:riz-p eny m- z ~2)-o-JUz-NriZ tm :H~ Ltll-caiz_-p eny m- z ~z)-o-~uz-Ntlz z z- -p eny m- z ~z)-o- r z . z- 3-p eny _ m-z ~
~-z o- z- z z- z- s- -p eny m- z ~z)-o- z- z CHz-CH(- n_ _p eny m_C(_~~z z ~z)-O-JUZ-NHZ H 1:H2-l=H(-l;HZ-pnenyl m-~z)-O-JUZ-NHZ H 1:H2-l:H(-1:H2-l:l-prieriyl m-NHz)_ o-JUZ-NHZ Z- Z- -p eny m- z NHz)_ -o- z- z z_ z_ 3-p eny m-C(-O~Z
~z)-O-~Uz-NHz z- z' 3- -p eny m- z NHz)_ o- z- z z- z- n- -p eny m- =O
~z)-o-JUZ-NHZ H l:Hz-l:H(-1;H2nl me p-NHz)_ O-JVZ-NHZ H l:Hz-l:H(-l;HZ-l:l-anllme p-~z)- , o-JVz-NHZ H 1,H2-l:H(-l.HZ-r-anllme p-L(=1VH)lVriz ~2)-O-JVZ NHZ H 1:H2-l.;H(-1:H2-1.H3 amlllle p-l:(=1VH)lVHy ~z)-O-JUZ-NHZ H liHZ-l;H(-l:Hz1;H3 V-anlllrie p-NHz)-O-1U2-NHZ H l:HZ-lJH(-l:HZlin-V-amllIie p-NHz)_ o-~Uz-NH2 H 2- z llie p-~z)-O-JVZ-NH2 H 2- 2- -and me p-~z)-o-5Uz-NHZ H Z_ z_ -and me p-~2)-O-JUZ-NHZ Y z' 3 am 1ne p-~z)-o- z z r z- 3 -am me _ p_C(_O)NHz NHz)_ O-JUZ-NHZ Y z- n- -and me p- z ~z)-o-5Uz-NHz i r eny -amino-car m- z oxy lc NHz)- acid - -o- z- z z- z- eny -ammo m_~~ ~NHz v1 1 11 1 NHz)- carboxylic acid o- r a r z- -p eny -amino m_ y 1.111.11 NHz)- carboxylic acid o- z z z- z' 3 p enyl-amino--m-C(=NH)NHz -v11 11 NHz)- carboxylic acid o- z- z z- r m-C(=NH)NHZ
trll V
s- -pheny amino NHz)- carboxylic acid o- z- z z- z- n- -p eny amino m- z NHz)- carboxylic acid O-JV2-NHZ H l:HZ-l:H(-l.;HZ-Ynenyl-amlllo m-l;(=ll)1VH2 CarOOXyIIC
NHz)- acid o-~uz-NHz H ~;Hz t.HIw:HZw:I-pnenyl-ammo m- z NHz)- carboxylic acid O-JVZ NHz H l:HZ l:H(-1:H2-r-pnenyl-arillnom-l:(=V)lVHz NHz)- carboxylic acid O-JVZ NHz H 1:H2 l:H(-1~t12-1x13-pneriyl-ammom-l=(=U)lVHz NHz)- carboxylic acid z c m z uo l NH2)- ic a d carboxy o- z- z z- z- n- -p eny -aminom-C(=O)NHz 17 t. ..
NHz)- carboxylic acid ~
o- z- z z- a y p enoxy-aceticm- z r NHz)- acid ester o- z- z z- r a Y -p enoxyaaehcrn-C(=~N)=IZ
NHz)- acid ester o- z- z I~ CHz-CH(-CHz-Methyl F-phenoxy-m- z acetic NHz)- acid ester o-5Vz Ntl2 H 1;ri2-lal(-l;ti2-Memyi l:rt3-pnenoxy-m- z NHz)- acetic acid ester o-~Uz lvrtz H laiz-cay-c.;tiz-a Y r -p enoxy- m- z NHz)- acetic acid ester o-~Vz-Ntlz ti (:rtz-Lti(-l:rlz-a y n_ -p enoxy m- z NHz)- acetic acid ester o- 2 z - H CHz CH(-CHz-a y enoxyacehc m- z NHz)- acid ester H z- r a y -p enoxyacehcm- z o- i z NHz)- acid ester o- z- z z- z- m-C(=O)NHz ...
erioXyacetic NHz)- acid ester o- z- z z- z- m-C(=O)NHz m ua m.m a a Y 3-p enoxy-NHz)- acetic acid ester o- z- z z- z- m-C(=O)NHz m ua m.ai v as a Y s- -p enoxy NHz)- acetic acid ester o- z- z r z- a y n- -p enoxy m- z NHz)- acetic acid ester o- z- z z z- enoxyacehc acid m-C(=NH)NHZ
~z)-o- Z 2 H CHz-CH(-CHz-C1-phenoxy-aceticm- z acid ~2)-o-S02-NHz H CHZ CH(-CHz-F-phenoxy- aceticm- z acid o-SO~ NHZ H CHz-CH(-CHz-CH3 phenoxy-aceticm-acid ~z)-o- 2 z H CHz-CH(-CHz-3- -p enoxy-aceticm- z NHz)- acid o- z- z H CHz-CH(-CHz-n- -p enoxy aceticm- z aci ~z)-o- Z-NHz H CHz-CH(-CHz-Yhenoxyacehc m- z acid ~z)-o- z-~z ~ z- z- -p enoxyacehc m- z aci NHz)_ o- z-NHz H z- z- -p enoxyacehc m- z aci NHz)-o- z- z z- z- 3-p enoxy-aceticm- z aci ~z)-o- z- z z- z- 3- -p enoxy aceticm- z NHz)- acid o- r z H z- r n- -p enoxy aceticm- z aci ~2)-o-JVz lVtiz r1 Lriz-Lril-1-nrenoxye ano m- z ~z)-o-wz-Nriz ti ~riz-~ry-~riz-la-pnenoxy-emanoim- z ~z)-O-JVz-Nriz ti laiz-qty-laiz-r-pnenoxy- etnanoim-~~=r~ry~riz ~2)-O-JUy-1Vt12 n l.tlz l.Yl~-1,ri2-1.113 pnenoxy-emanoim-~~=mry~ri2 NHz)_ o-auz-Nriz tm :riz-l:ry-l:rizl:ri3-V-pnenoxy-emanoim-1:~=~ry~riz ~z)-o-z- z z- z- n--p v~ ..~~y..
epoxy m-a ano NH2)_ -2- 2 2- z' enoxye m-C(=O)NHz ano a as ua a ~2) o-z- z z- z- m-C(~jNHz v..a as ua a -p enoxye ano ~2) o-z- z z- z- -p m-C(=O~NHz epoxy-a ano a' as ua a ~2)-o-z z z- z- 3-p m-C(=O)NHz epoxy-ethanol NHz)_ O-SUz-NHZ H l:Hy-l:Hl-l:Hz1:H3-V-pherioxy- m-ethanol ~2)-o-~Vz-NHz H MHz-LHl-LHz-tsn-V-pnenoxy- m- z ethanol ~z)-O-JUy-NHZ H l:HZ-l:Hl-l:HZMethyl m-pnenOXy-eLllyl NHz)- ether o-JUz Hz H ~alz-LHl-trHZ-lmemym;l-pnenoxyeulyl m-t.l=lvrylrriz 1v NHz)- ether O-5UZ-NH2 H C:HZ-C:HI-I:HZ-lVleUlyl m-l;l=1VH)1VH2 r-pheriOXy-emyl lVHz)- ether o-JVz-NHZ H 1;H2-(:Hl-l;Hz-Melllyll:H3-prienOXy- m-NHz)- ethyl ether O-JUz-NH2 H LHZ-LHl-~atz-a m- z Y
s--P
epoxy-NHz)- ethyl ether o-SVz-NHz H ~:Hz-c:Hl-t,Hz-a m- z y n_ -p epoxy NHz)- ethyl ether o-SUz-NHz H ~;Hz -t,HZ-a m- z Lttl y enoxye y NHz)- ether O-JVZ-NHz H I;HZ -l.;HZ-a m- y call y -p eriOXye y NHz)- ether o-~UZ Hz H 1:H2-l:Hl-l.;HZ-Memyl m- y N r-pneriOXyemyl NHz)- ether o-JVZ-NHZ H 1;t12-l:Hl-1:H2-a m- z Y
s-NHz)- phenoxyethyl ether o-JVZ-NHZ H 1:H2-l:Hl-l:Hz-i Vlemyll:rlg-v- m-NHz)- phenoxyethyl ether o-JUz-NHz H ~;Hz-fall-LHZ-t vlemyl m-~l=m~lvriz tsn-v-NHz)- phenoxyethyl ether o-z- z s z P m- z ehY
o-z- 2 3 2 -P m-C(-~)~z ehY
o-r z s z -P m-~;l=lvtl~lvti2 enY
o-z- 2 3 2 9-P m- z enY
o-z- 2 3 2 3- p eny m-~l=lvrl~lvriz -o-z- z s z n_ eny m- z _p o-z- z s z P m-t,l=U)lvti2 ehY
o-2 2 3 2 -P m- z enY
o-z- z s z -P m- z enY
o-z- 2 3 2 3-p m- =O)~2 eny o-z- z a z 3- p eny m- z -r z s z n_ eny m-_p o-z- z s z me P- )~z o-r z s z -am p-C(=NH)NHz me o-z- z s z -and p- z me o-z- z s z 3-am p- z me o-z- z 3 z 3- p- z -and me o-z- z a z n- p-C(=NH)NHz _~
me o-z- z s z m p- z me o-z- z s z -am p_ me O-z- z s z -aIll p- 2 1ne o-z- z s z 3-3niI-me p- NHz o-z- z s z 3- p- z -am me o- z- z 3 z n_ p~(_O)~z _am me o- z- z ~ z eny m-C(=NH) -ammo-carboxylic z acid o-JUz-NHz 3 z eny m- z -ammo carboxylic acid o-JUZ-NHZ 1x13 1.;H2 r-pnenyl-amlllo m-l:(=NH)NH2 carboxylic acid o-~Vz-NHz LH3 MHz ~H3-pnenyi-ammo m-~(=Nri)Nriz carboxylic acid o-JUz-NHy 1:H3 1;H2 1x13-u-pnenyl m-l;(=NH)NHZ
amlIlO
carboxylic acid O-JUy-NHz c:H3 ~:Hz rsn-u-pnenyi m- z ammo carboxylic acid O-JV2-Nriz c:H3 ~:Hz rnenyi-ammo m-~;~=u)ivtiz carooxync acid O-JUZ-NHZ ~H3 ~tiz m-pnenyi-ammo m-~~=~)Nriz CH3carboxylic acid o-auz NHz uH3 ~:HZ r-pnenyi-ammo m-~t=~)wriz carboxylic acid O-~Vz-NHz ~H3 uHZ ~H3-pnenyi-ammo m-~~=v)Nriz carboxylic acid O-lUZ-NH2 l:Hg l;HZ 1;H3-u-pnenyl-am111o m-carboxylic acid o- z- z s z n- m-C(=O)NHz -phew=ammo -carboxylic acid o- z- z CH3 CHz Methyl m- z phenoxy-acetic acid ester o- Oz-NHz CH3 CHz Methyl m- z C1-phenoxyacehc acid ester o- z- z CH3 CHz Methyl m- z F-phenoxy-acetic acid ester o-5V2-Nriz c:H3 ~:Hz Memyi m- z pnenoxy-acetic acid ester o- z- z s z a m- z y -p enoxy-acetic acid ester o-5Uz-Nriz LH3 LHz Memyi m-~~=Nri)Nriz tsn-u-pnenoxy acetic acid ester -o- z z s z a m=C(=O)NHz y enoxyacetic acid ester o- z z CH3 CHz Methyl m-C(=U)NHz C1-phenoxyaceric acid ester o- r z ~s CHz Methyl m- z F-phenoxyacehc acid ester o-5Vz-NHz (:H3 c~Hz a m- z y 3-p enoxy-acetic acid ester o-SVZ NHz LH3 ~:Hz Memyi m- z ~H3-u-pnenoxy acetic acid ester O-SUZ-NH2 c:H3 ~:Hz a m- z y n--p enoxy acetic acid ester o- z- z a z enoxyacehc m- z aci o- r z s z -p m-C:(=NH)NHz enoxy-acetic aci o- z- z 3 z -p m- z enoxy-acetic aci o- z- z ~ z 3- p enoxy-acericm- NHz aci o- 2 2 3 2 3 m-(:(=NH)NHz -p enoxy-acetic acid o- z- z s z n- m- z -p enoxy.aceric aci o- z- z s z enoxyacehc m- )NHz aci o- z- z s z -p m- NHZ
enoxyacehc aci o- z- z 3 z -p m- z enoxyacehc aci o- z- 2 3 z g- p epoxy-aceticm- NHz aci o- r 2 3 2 3- -p epoxy aceticm- )NHz aci -o-z- z 3 z n- m- NH2 -p ienoxy acehc aci o-z- z 3 z enoxye m-C(=NH)N
ano z -o-z- z s z -p m-C(= z epoxy-a ano o-r z s z -p m- z epoxy-a ano c-z- z s z 3- p m~NH) z epoxy-a and o-z- 2 3 2 3- - p epoxy-a m- Hz ano n-r z s z n- epoxy a m-C(= z -p ano o-z- z s z enoxye m- z ano o-z- z a z -p m- NHZ
enoxye ano o-z- z s z -p m-C(=O)NHz epoxy-a ano z- z 3 z ,-p m- z epoxy-a ano 2 2 3 2 3' p epoxy- m- z - a ano o-z- z s z n- epoxy- a m- NHz -p ano o-z- z s z a m=C(=N~NHz Y
P
epoxy-a y ether o-~uZ Hz UH3 Uriz nnemyi m-~~=~rywriz 1v m-pnenoxyemyi ether o-JUz-iVriz l:Hj 1:H2 lVleLriyl m-l.;(=1VH)1VH2 r=pneriOXy-e2llyl ether o-SUz Hz c:H3 LHz enemy m- z 1v LH3-pnenoxy-ethyl ether z- z 3 z a m- z y -p epoxy-ethyl ether o-5Uz-iVHz 1:H3 ~:Hz Metnyt m-~:(=lrri)~riz tsn-u-pnenoxy ethyl ether o-JUZ-NHZ 1;H3 lai2 a m-y enoxye y ether o-5Uz-NHz c:Hj ~:Hz a m- z y -p enoxye y ether o-5Uz-NHz c:H3 LHz Memyi m- z r-pnenoxyemyi ether o-5Uz-NHz C.;H3 (:Hz a m- z y phenoxyethyl ether o-5Uz-NHZ C:Hj l:Hi MeTtlyll;H3-U- m-phenoxyethyl ether o-5Uz-NHz C;H3 c:Hz lvlernyl m- z tsn-u-phenoxyethyl ether o-z- z s z- z P m- z enY
o-z z 3 z- z -P m- z enY
o-z- z 3 i z -P m-C(=~)~z enY
z- z 3 z- 2 3- P m- z enY
o-z z 3 z- z 3- - p eny m- NHz o-z- z s z- z n_ eny m=C~ ~)~z -p o-z- z 3 z- z P m- ~z enY
c-z- 2 3 2- z -P m- ~z enY
o-2 2 3 2- z -P m- z enY
o-z- z s z- z 3 p m-eny z- z 3 z- z 3- - p eny m- NHz o-z- z 3 z- z n_ eny m-~~=v~r~riz _p o-z- z 3 z- z m p- z me r z 3 z- z -am p- (=~)~z me z- 2 3 2- z -am p- z me o-z- 2 3 2- z 3-am p- )NHZ
me c-r z s z- z 3- p-t,~=r~ry~riz -am me o-z- z s z- z n_ p- z _anl me a-z- 2 l 2- z me P- NHz o-r z s z- z -am p-me o-z- z s z z -am p- z me -o-z- 2 3 2- z 3-am p- Hz me -o-z- z s z- z 3- p- (=O)NHz -am me o_z_ z CH3 z- z n- P- z -am me o-z- z CHj z- z eny m-C = z -ammo-car oxylic acid o-SUz-NHz 3 (:Hz-(:Hz C1-Phenyl-arrimo m-C:(=NH)NHz carboxylic acid o-~uz-ivtiz ~rij ~riz-~riz r-pnenyi-ammo m-~t=r~ryNriz carboxylic acid o-JUz-NHz l;rlj lalz-lalz Cal3-pnenyl-amlrio m- z carboxylic acid o-~uz-NHz ~n3 r z 3- m- z -p eny ammo carboxylic acid O-JUz-Nriz 3 z- z n- m- z -p eny ammo carboxylic acid o-~uz-lvriz ins ~riz-~riz rnenyi-ammo m- z carooxync acid o-JVz-Nri2 1x13 ~;tlzWa1z t_;1-pnenyi-ammo m- z carboxylic acid O-JUz-NHz Lti3 ~aiz-Ltiz r-pnenyi-amino m-~:~=v)~riz carboxylic acid o-~Vz-Nriz caij ~:riz-Ltiz ~ai3-pnenyi-ammo m- z carboxylic acid o-5Uz-Nriz cai3 ~aiz y ai3-u-pnenyi-ammo m-~:(=uJr~tiz ca carboxylic acid O-JVz-NHz Lti3 Ltiz aiz nn-u-pnenyi-ammo m-~~=v~~riz c carboxylic acid o-z- z 3 z- z a m- z y p epoxy-acetic acid ester o-z- z CH3 CHz-CHz Methyl m-C(=NH)NHz C1-phenoxyacetic acid ester o-SOZ-NHz CH3 CHz-CHz Methyl m- z 1'-phenoxy-acetic acid ester o-z- 2 3 2- z a m- z Y
a-P
epoxy-acetic acid ester o-JVz-Nriz Lti3 Ltiz riz a m- z ~ y ,--p epoxy-acetic acid ester O-JVi Hz LH3 c:riz-~ttz Memyi m- z N nn-u-pnenoxy acetic acid ester o-z- z - CH3 CHz Hz Methyl m-C:(=V)NHz C Yhenoxyacehc acid ester o-z- z CH3 CHZ Hz a m- z C y -p enoxyaceric acid ester o-z- z Hs r z a m- z y -p enoxyacehc acid ester o-SVz-NHz C.H3 t;tiz-t;riz nnemymai3-pnenoxy- m- z acetic acid ester o-5Uz-NHz c,tij ~:riz-~aiz nnemymai3-v-pnenoxy m- z acetic acid ester o-SVz-Nriz t.ri~ c:riz-~;tiz Memyi m- z tsn-v-pnenoxy acetic acid ester o-z- 2 3 2- z enoxyacehc m- z act o-z- 2 3 2- z -p m- NHz epoxy-acetic act o-z z s z z -p m- z epoxy-acetic act Y 2 3 2- z 3- p epoxy-aceticm-C;(=NH)NHz act o-z- z s z- z 3- m- z -p epoxy-acetic acid o-z- z s z- z n- m- z -p epoxy acetic act o-r z s r z enoxyacehc m-C(=U)NHz act o-z- 2 3 2 2 -p m- z enoxyacehc act o-z- z s z- z -p m- z enoxyacehc act o-z- z s z- z 3-p m- z epoxy-acetic act o-z- 2 3 2- z 3- m- )NHZ
-p epoxy acetic aci o-z- z a r z n- m- z -p -enoxy acehc aci -o-r z 3 z- z enoxye m-C(=NH)NHz anol z- 2 3 2- z -p m- z enoxy-a ano --o-z- z a z- z -p rn-C(--NHjN>
enoxy-a anol -o-z- z s z- z 3-p m=
enoxy-a ano o-r z 3 z- z 3- p enoxy-a m- z - ano o-z- z 3 z- z n_ enoxy a m-~~=wrywriz _p ano o-z- z a z- z enoxye m- z ano -o-z- z 3 z- z -p m-C(=O
enoxye anol o-z- z 3 z- z -p m- z enoxy-a ano o-z- z 3 z- z 3- p m-~~=v~ivtiz enoxy-a ano o-z- z 3 z- z 3- - p enoxy- m- z a ano o-z- z 3 z- z n- enoxy- a m- z -p ano -o-z- z s r z a m-C(=NH)NHz Y
P
enoxy-a y ether o-5U2-Nriz 1:H3 l;Hz Hz lVlemyl m-l; l:1-prienOXyeillyl ether o-5Uz-NHz ~;H3 ~:HZ Hz Memyi m- z L r-pnenoxy-etnyi ether o-5Uz-NHz 1;H3 1;H2-C.HZ Melllyll:H3-pnenOXy- m-l;~=lVt1)lVrlZ
ethyl ether O-5uz-NHz Sri, c:Hz-LHz nnemyi m- z ~ri3-v-pnenoxy-ethyl ether o-5uz-NHz c:H3 ~Hz-~ Hz nnecnyi m- z rsn-v-pnenoxy ethyl ether o-5Uz-NHz c:H3 c:Hz-LHz lvlemyi m- z rnenoxyemyi ether o-5Uz-NHz c:H3 LHZ Hz Memy m- z L m-pnenoxyemy ether o-~u2 Hz c:H3 MHz tiz Memyi m-~~=~yvmz N ~ r-pnenoxyemyi ether O-JUz-NHZ C:H3 C:HZ-1;H2 MeUlyll;rij m-phenoxyethylether o-5Uz-NHZ (:H3 C:HZ-l~Hz Memy1 m-l;(=V)lVrlz C;H3-u-phenoxyethylether O-JVZ-NHZ C.;H3 l;Hz-l:Hz Melllyl m-li(=V)1vt12 tiri-V-phenoxyethyl ether o-z- 2 3 2- r z P m- z enY
o-r z 3 z- z-z -p m-~.~=mnyvtiz eny z- 2 3 2- z-z -p m-eny o-z- z 3 z- z-z 3- P m- z enY
o-z- 2 3 2- z-z 3- - p eny m-C(=1VH)NHz o-z- 2 3 z- z-z n_ eny m_ )NHz _p o-2 2 3 2 2 2 P m- (=a)~z enY
o-r z 3 z- z-z -P m- z enY
o-z- 2 3 2- z-z -p m-L(=V)lvtiz eny 2- 2 3 2- 2 2 3- p m- z eny 2 2 3 2- 2 2 3- - p eny m- z z- 2 3 2- z-z n- eny m- z -p o-z- z 3 z- z-z m p- z me o-z- z 3 z z-z -am p- z me z- 2 3 2- z-z -am p-~~=mnyvriz me o-z- z s z- z-z 3-am p- z me o-z- z 3 z z-z 3 p- NHz -am me o-z- z 3 z- z-z n- p- z -$m me o-z- z s z z-z m p- ~_O)NHz me o-z- z s z- r z -am p- z me o-z- z s z- z-z -am p-~;~=v)lvttz me z- z 3 2- z-z ; p- N
am me z- 2 3 2- z-z 3- P- NH2 -am me o-z- z s z- z-z n- p-~;(=U)ivttz -am me o-z- z ~ 3 z- z-z eny m- z -ammo-car oxy is acid o-JVz-NHz j z- z-z eny m- z -ammo carboxylic acid o-~Vz-NHZ 1x13 LHz-LHz-~-Hz r-pneriyl-ammo m-l:(=Ntt)iVtlZ
carboxylic acid o-JVZ HZ lal3 LHz-LHz-~-HZ ~-Hs-pneriyl-ammo m-N carboxylic acid o-JVZ-NHZ laij 1x12-Caiz-~;tiz 1;t13-V-prienyl m-t:(=Nti)iVtiz ammo carboxylic acid o-auz-Ntiz ~ri3 ~HZ-~HZ-~HZ ~sn-u-pnenyi m-~(=~ri)Nriz ammo carboxylic acid o-JVz-Ntiz Lti3 ~:HZ-LHZ-LHz rnenyi-ammo m-~(=v)Ntiz cardoxyiic acid o-JV2-NH2 C:ri3 l:rizalzri2 l:l-phen yl-amlllo m-l:(=V)Nri2 l 1; carboxyl ic acid O-JUz-NriZ Lti3 ~HZ-~HZ-~HZ r-pnenyi-ammo m-~(=v)mriz carboxylic acid O-JUz-NH2 c:H3 Ltiz-~aiztiz ~;ti3-pnenyi-ammo m- z L carboxylic acid o-JVz-Nriz LH, ~tiz-Ltiztiz ~ti3-u-pnenyi-ammo m-~(=u)Nriz L carboxylic acid o-JU2-Ntlz (a13 ~-HZ-~-HZ-LHz tsn-u-pnenyi-ammo m-~:(=~Jr~riz carboxylic acid o-r z 3 CHz-CH2Hz Methyl m- z C phenoxy-acetic acid ester o-z- z 3 CHz-CHz-CHz a m- z y -p enoxyacehc acid ester o-z- z , CHz-CHz-CHz a m- z y -p epoxy-acetic acid ester o-5Uz-Nriz LH, caiz-~;t12tiz a m- z L y 3-p epoxy-acetic acid ester o-5Vz-NHZ 1;H3 ~-H2-~-riz-~-HZ Meulyl m-~a13-v-pnenoxy-acetic acid ester o-JVz-NHz 1:H3 LHz-Lriz-~-Hz Methyl m- z tsn-u-pnenoxy acetic acid ester o-r z s CHz-CHzHz Methyl m-C(=U)NHz C Yhenoxyacehc acid ester o-SOZ Hz CH3 CHz-CHzHz Methyl m- z N C Cl-phenoxyacetic acid ester o-SOz~lH2 CH3 CHZ HZHz Methyl m-C(=U)NHz C C F-phenoxyacehc acid ester o-~uz-NHz t;H3 c:riz-~tiz-~tiz Memyi m-~(=~)r~riz ~ri3 pnenoxy-acetic acid ester z- 2 3 2- z-z a m- z Y
a--p epoxy acetic acid ester z- 2 3 2- z-z a m- z y n--p epoxy acetic acid ester o-z- z 3 z- z-z enoxyacehc m- z aci o-z- z s z- z-z -p m- (~NHz epoxy-acetic aci o-z- z s z- z-z -p m- z epoxy-acetic aci o-z- z a z- z-z 3- p m-C(=NH)NHz epoxy-acetic aci O-SOz-NHz 3 z z-z 3- m- z -p epoxy-acetic acid o-z- z s r r z n- m- z -p -epoxy acettc aci o-z- z s r z-z enoxyaceric m- NHz aci o-z- 2 3 2- z-z -p m- NHz enoxyacehc aci o-r z ~ r r z -p m- =O)NHZ
enoxyacehc aci o-z- z 3 z- z-z 3 m- N
p epoxy-acetic aci o-z- 2 3 2- z-z 3- m- NHz -p epoxy acetic acl o-z- z 3 z- z-z n- m- Hz -p epoxy acehc acl --o-z- z ~3 z- z-z enoxye m-C(--NH) ano z o-r z 3 r r z -p m- z epoxy-a ano o-z- 2 3 2- z-z -p m- ~~ z epoxy-a ano o-z- z 3 z- z-z 3- p m- z epoxy-a ano o-z- z 3 z- z-z 3- - p epoxy-a m- z ano o-z- 2 3 2- z-z n- epoxy ethannolm-C(=NH)N
-p o-z- 2 3 2- z-z enoxye m- z ano --o-z- z 3 z- z-z -p m~
enoxye ano o-z- z 3 z- z-z -p m- (=O z epoxy-a ano o-z- z 3 z- z-z 3-p m- z epoxy-a -ano o-z- z 3 z z-2 3- p epoxy- m- z - a ano --o-z- z 3 z- z-z n- epoxy- m=C(=O)NHz -p ethanol -o-r z 3 z- z-z a m-C(=NH)NHz Y
P
epoxy-a y ether O-JVz-Ntiz ~ti3 ~riz-~tizriz a m- z ~ y -p enoxye y ether o-~V2 tiz Lti3 ~tiz-~rizaiz nnemyl m-~~=mriJmriz N c r-pnenoxy-emyl ether o-r z s z- z-z a m- z Y
3-p epoxy-ethyl ether O-JVZ-Nt12 Lti, ~riz-~:riz-~riz Memyl m-~~=rrryvriz ~ri3-V-pnenoxy-ethyl ether O-JUZ-NriZ c:rt3 ~:l~z-Lnz-Lnz Menlyllsn-V-pnenoxy m-~,~=mryvriz ethyl ether O-SVz-NHz ~ti3 Ltiz-caiztiz nnemyl m-~~=V~rrriz ~ rnenoxyemyl ether o-SUZ-Nriz Lti3 Ltiz aizriz Memyl m- z c c: ~l-pnenoxyemyl ether o-5Vz-Nrtz cai3 Ltiz tizw;riz nnemyl m- z c.; r-pnenoxyemyl ether o-JVz t12 1;113 1;112-t~ttz-~;ttz ivietnyl m- z N :ri3-phenoxyethyl ether o-~UZ-Nt12 C:H3 ~aiz rtzriz Memyl m- z c.; ~ ~ri3-V-phenoxyethyl ether o-5Uz-NtlZ Ltl3 (.;t12tiztiz a m-~; t, y n--phenoxyethyl ether o-z- z 3 r 3 P m- z - enY
o-z- z 3 z- 3 -p m_C~_~)NHz - eny o-z- z 3 z- 3 -p m-- eny o-z- 2 3 2- 3 3-P m- =~~z - enY
o-z- z 3 z- 3 3- P eny 111- z - -o-r z 3 z- 3 n- eny m- z - -p o-z- z 3 z- 3 P m- z - enY
o-z- 2 3 2- 3 -p m- (=O)NHz - eny o-z- z 3 z- 3 -p m-- eny o-r z 3 z- 3 3-p m-- eny o-z- 2 3 2- 3 3- p eny m-C(=O)NHz - -o-z- z 3 z- 3 n- eny m-- -p z- 2 3 2 3 m p- (~H)NHz - me o-z- z 3 z- 3 -am p-L(=wri)lVriz - me 2- 2 3 2- 3 -anl p-l.(=1V
- lne rl)1V rlz 2 2 3 2- 3 3 p-l~~=lVt1)1Vt12 - a me 2- 2 3 2- 3 3- p-- -and me 2- 2 3 2- 3 n- p- z - -am me 2 2 3 2- 3 m p-~:~=V~rrriz - me _ 2- 2 3 2- 3 -am P- )~Z
' me 2- 2 3 2- 3 -anl p-l.(=V)1Vt12 - lne 2- 2 3 2- 3 3-am p- ~NH2 - llle o-z- z 3 z- 3 3- p- =O)NHz - -am me -o-z- z z- 3 n_ p-C(_O) _ _am z me o-z- z ~s r 3 eny m-C(=NH
- -ammo-carboxylic z acid o-auz-NHz ~ri3 ~;tiz-~H(-LH3)-LI-rnenyl-ammo m-~l=NH)NHz carboxylic acid O-JUz-NHz ~:H3 trHZ-jai(-LH3)-r-pnenyi-ammo m-~l=ivti)Nriz carboxylic acid O-JVZ H2 1:ri3 l:HZ-l:ril-1:H3)-~ti3-pnenyi-ammo m-~l=rVri)Nriz N carboxylic acid O-JUZ-NHz cai3 ~HZ -~ti3)-~H~-u-pnenyi m- z ~Hl ammo carboxylic acid O-JUZ-NHz ~H3 ~;tiz-aril-~ti,)-tsn-u-pnenyi m- z ammo carboxylic acid O-JVZ-NHZ c:H3 ~aiz-LHl-LH,)-rneny-ammo m- z cardoxync acid o-JUZ Hz C.;H3 l;tiz-l:Hl-l:Hj)-l:l-prienyl-ammo m- z N carboxylic acid O-JVZ Hz 1;H3 l:HZ -l:Hg)--p m-N l.;Hl eriy -amino carboxylic acid o-JUz Hz t;ti3 ~;HZ w:113)w;tl3-Pneny-ammo m- z N t_;H1 carboxylic acid o-~Uz Hz (:H3 ~;tiz -~:H3)-~:ri3-u-pnenyl-ammo m- z N fail carboxylic acid o-5Uz-NHz 1:H3 1:H2-l.:H(-1:H3)-tan-U-prieriyl-aIri1I10 m- y carboxylic acid o-z- z CHj CHz-CH(-CH3)-Methyl m-C(=NH)NHz phenoxy-acetic acid ester o-z- z CH3 CHz-CH(-CH3)-Methyl m- z CI-phenoxyacehc acid ester o-z- z CH3 CHz-CH(-CH3)-Methyl m-C(=NH)NHz 1~~-phenoxy-acetic acid ester o-~u2 Hz LH3 Ltiz-~til-~H3)-Metnyi m-~l=mry~riz N ~ri3-pnenoxy-acetic acid ester o-5Uz Hz C:H3 ~:HZ -LH3)-Memym:H3-u-pnenoxy- m- z N ~;Hl acetic acid ester o-5Uz Hz C:H3 ~:Hz-(_:H(-~;H3)-Meuiyl m- z N tsn-u-pnenoxy acetic acid ester o-r z CH3 CHZ -CH3)-Methyl m- z CH( Yhenoxyacetic acid ester o-z- z H3 CHz-CH(-CH3)-Methyl m- z C1-phenoxyacetic acid ester o-z- z Hs z- 3 a m- z - y -p enoxyaceric acid ester o-z- z s z- 3 m-C(=O)NHz - ava ua .
w...
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a Y
3-p epoxy-acetic acid ester o-r z 3 z- s =n-C(=O)NHz - ava ua m.m v a a Y
s--p epoxy acetic acid ester -z- z s z- 3 m-C~ O)NHz - avr ua a L
v as a y n--p epoxy acetic acid ester o-z- z 3 r 3 enoxyacehc m-- aci -o-z- z 3 z- 3 -p m- z - epoxy-aceric aci o-z- z s z- 3 -p m-C( NH)NHz - epoxy-acetic aci z- z s z- 3 3- p epoxy-aceticm-C(=NH)NHz - aci o-z- 2 3 2 3 3 m- 1VFI)NHz - -p epoxy-aceric acid o-z- z s r s n- m-C(=NH)NHz - -p epoxy acetic aci o-z- z , z- , enoxyacehc m- z - aci o-z- z 3 r j -p m-- enoxyacetic aci o-z- z 3 z- , -p m- =O)NHz - enoxyaceric aci o-z- 2 3 2 3 s- p epoxy-aceticm- z - aci o-z- z 3 z- s s- -p epoxy aceticm--aci -o-z- z CH3 z- , n- m-C(=
- -p epoxy acetic acid o-z- z CH3 z- 3 enoxye m~NH)RHz - ano o-z- z s z- s -p m- z - - epoxy-a ano o-z- z s z- 3 -p m- z - epoxy-a ano o-z- 2 3 2 3 ~ri3-pnenoxy-emanoi m- z -o-SOz-R~Z , CF>-z- 3 3- p epoxy-ethanolm-C(=NHjNHz - -o-z- z s r 3 rsn-U-p nenoxy emanoim- z - -o-z- z s z- 3 enoxye m-C( - ano o-z- z 3 r 3 -p m- z - - enoxye ano -o-~ 3 z_ 3 _phenox~y-et m-C(=O)NF~Z
_ anol z- 2 3 2 3 ; p m- z - epoxy-a ano o-~O~-Nzl~ 3 z- j 3= O=plienoxy- m-C(=O)NHz - ethanol -o-r z s z- 3 n- enoXy= m-C(=O)NHz - -P a ano -o-z- z 3 z- 3 a m- =z - Y ..~
p epoxy-a yi ma ua a a um ether o-z- z s z- s m-C( NHjNHz - m ua m.a m a Y
-P
enoxyethyI
ether o-z- 2 3 2- 3 a m-C(=NH)NHz - Y
-P
epoxy-a y ether o-z- z s z- s -m-C(=NH)NHz - ma m i a..ia a a Y
j P
epoxy=
-ethyl ether -o-r z s z- s m-C(_~)~z - ivi ua i ~aa v a Y
-Phenoxy-ethyl ether o-z- z s z- s a m- =NH)IVHZ
- Y
n--p epoxy ethyl ether o-z- z s z- s a m_C(=O)NHz - y enoxye y1 ava ua a a a m ether o-z- z 3 2 3 a - y v~ v~..a -p m-enoxye y ether o-z- 2 3 2 3 a m-C(=O)NHz - Y
_P~~yl ether O-JVz-NHz C:ri3 l:riz-(:ri(-1:ri3)-Mettlyll:ri3 m-phenoxyethyl ether o-JUz-Ntlz l;tlg lalz-lal(-1x13)-lVlelllyl m-l;(=U)1Vt12 1x13 U-phenoxyethyl ether o-5Uz-iVtiz cal3 caiz-Vtl(-c:ri3)-Metny m-~t=v)r~tiz tsn-U-phenoxyethyl ether o-z- z s z- z P m- z - enY
z- 2 3 2- z -p m- =NH)NHz - eny o-z- z 3 z- z -p m-~:(=~ti)mttz - eny o-z- z s z- z s-P m- z - enY
_ o-z- z 3 z_ z 3 p eny m.C(=~)~z _ -o-z- z 3 z- z n- eny m- z - -p _ o-z- z s z- z p m- _ ~~z - eny o-z- 2 3 2- z -p m-~t=U)~riz - eny Y 2 3 2- z -p m-- eny o-2 2 3 2- z s-P m- =O)NHz - enY
o-z- 2 3 2 2 3- p eny m-C(=O)NHz - -o-r z Lri3 z z n- eny m-i.I=U)mriz - -p -o-z z s z- z t p- Z
- me _ o-z- z s z- z -am p_ ~z - me o-z- z 3 r z -am p- )NHz - me o-z- z s z- z 3-am p-~a=wti)mriz - me o-2- z s z- z a- p_ - -~
lne o-z- z s r z n- p_ 2 - -am me o-r z 3 z- z m p- z - me o-z- z 3 r z -am p- )NHz - me o-z- z 3 z- z -am p- )NHz - me o-z- z 3 z- z 3-am p- N z - me - -~
~e o-z- z CH3 z- z n- P-C(=O
- -am me o-r z CH3 r z eny m- z - -ammo-car oxy is acid o-~uz-NHz s z- z eny m- z - -ammo carboxylic acid o-z- 2 3 2- z -p m- riz - eny -ammo carboxylic acid o-z- z m-C(=NH) v11 v11 -111 v11 z s v11~ ~ 11 111 r z 1 p eny -amino --carboxylic acid O-JUz-NHz ~H3 MHz-~Hl-NHZ)-c:H3 m- z u-pnenyi ammo carboxylic acid O-JVZ-Nri2 ~H3 ~riZ -Nriz)-tsn-u-pnenyi m- z ~Hl ammo carboxylic acid o-~uz-NHz uH3 LHz-uHl-NHz)-rnenyi-ammo m-~l=u)wriz cardoxyiic acid o-~uz-Ntiy :ri3 ~aizw;ry-wriz)-~i-pneny-ammo m-~.l=u)ivriz carboxylic acid O-JVz Hz uH3 ~riz-aril-wriz)-r-pnenyi-ammo m-~l=u)wriz N carboxylic acid O-JUZ-Nri2 uH3 ~riz -wriz)-~ri3-pneny-ammo m-~l=u)wriz aril carboxylic acid O-JVZ-Nriz ~ai3 ~rizw:ril-wtiz)w;ti3 m-~;l=v)ivriz u-pnenyi-ammo carboxylic acid o-JUG Hz c:H3 LHz-~:Hl-NHz)-tsn-u-pneny-ammo m-~l=u)mriz N carboxylic acid o-z- z a z- z m-C(=NH)NHz - lYl a y p epoxy-acetic acid ester o-z- z ~ z- z a m-C(=NH)NHz - Y
-p enoxyacehc acid ester o-z- z s z- z iri-C(=NH)NHz - lYl 11~
a y -p epoxy-acetic acid ester o-z- z a z z a m- )NHz - Y
3-p epoxy-acetic acid ester o-~u2-NHz LHj LHz-~Hl-NHz)-a m- z y ,--p epoxy-acetic acid ester O-JVZ-NHZ ~;H3 ~aiz -ivtiz)-metnyi m- z Lril tsn-v-pnenoxy acetic acid ester o-Oz-NHz CHj CHz-CH(-NHz)-Methyl m- z Yhenoxyacehc acid ester o-02-NHz CH3 CHz-CH(-NHz)-Methyl m- z C1-phenoxyacehc acid ester o-z- z CH3 CHz-CH(-NHz)-Methyl m-C(=U)NHz )-phenoxyacehc acid ester o-~uz Hz ~;H, ~aiz-~til-wtiz)-enemy m-~.l=~)mriz N ~ri3-pnenoxy-acetic acid ester O-JVZ-NHZ ~:H3 ~;Hz-c:Hl-wtiz)-metnymai3 m-~,l=u)ivriz v-pnenoxy acetic acid ester O-JUZ-Nriz l~H~ l:Hz -mtiz)-nnetny m-~;l=~)mriz ~,Hl tsn-u-pnenoxy acetic acid ester o-z- 2 3 2- z enoxyacehc m- z - aci o-i z s z- z -p m-C(=NH)NHz - epoxy-acetic aci o-z- 2 3 2- z -p m- )NHz - epoxy-acetic aci z- 2 3 2- z 3-p m-- epoxy-acetic aci o-z- z s r z s- m-C;(=NH)NHz - -p epoxy-acetic acid o-z- z 3 z- z n- m- (=NHjNHz - -p epoxy acetic aci o-z- z 3 z- z enoxyacehc m- z - aci o-z- z 3 z- z -p m- z - enoxyacehc aci o-z- z 3 z- z -p m-- enoxyacehc aci o-z- z s r z 3- p epoxy-aceticm-- aci o-z- 2 3 2- z 3 -p epoxy aceticm- z -aci o-r z 3 z- z n- m- =O z - -p enoxy acetic aci -_ - - z ~3 z_ z enoxye mz _ ano o-z- z ~3 z- z -p m-C(=NH)NHZ
- enoxy-a anoI
o-z- z a z- z -p m~~N~NH2 - enoxy-a anol o-z- z a z- z 3- P m- (= z - enoxy-a ano -o-z- 2 3 2 2 s- - P enoxy-a m-C( - ano o-r z s z- z n- enoxy ethanolm-C(=NH)NHz - -p o-z- 2 7 2 z enoxye m-C(=O z - ano -z- 2 3 2- z -p m-C(=~jNH2 - enoxye -anol o-r z , r z -p m- (=O)N>=I2 - enoxy-a -ano -o-z- z s z z 3-p m-C(=O)NH2 - enoxy-a -ano -o-z- z 3 r z 3- p enoxy- mC( z - - a ano --o-z- z 3 z- z n- enoxy- a ~~O~NHZ
- -p ano o-z- z s r z a ~(=NH)NHz - y p enoxy-a y ether O-JUZ-Nt12 tai, z- z a m- z - y -p enoxye y ether o-z- z a z- z m-C(=NH)NHz - iva m a t-a y -phenoxy-ethyl ether o-z z s z- z a m- (=NH)NHz - Y
3-p enoxy-ethyl ether o-JUZ-NHZ 1x13 Calz l-lVriz)-MeLriyi m-l;l=iVtl)lVtlz tai 1;t13-V-prieriOXy-ethyl ether O-JUz-NHz 1x13 lalz-l~ril-lVriZ)-lVleLilyi m-l:l=1Vri)lVtlz i3ri-u-pnenOXY
ethyl ether o-JVZ-lVri2 ~ai3 ~:nz-~-nl-~nz)-Meuiyi m-~l=m)mriz rnenoxyemyi ether O-JU2-Ntl2 lal3 lalz-fail-lVri2)-lVleLtlyi m-l:l=V)lVriz la-pneriOXyeTriyi ether o-5c~ztiz Lti3 r z a m- z iv - y -p enoxye y ether o-5Vz tiz ~:ri3 r z a m- z N - y 3_ ..
phenoxyethyl ether o-z- z s t z a m-C(=O)~z - Y
s-phenoxyethylether o-z- z s t z m-C(=O)NHz - ...
et it~y 13n-O-phenoxyethyl ether o-z- z a z- - p in- z n eny -o-r z 3 z - -p m- (=NH)NHz n eny -o-z- z s z- - -p m- z n eny _ o-z- z s z- - 3- p m-~:l=i~ti)wtiz n eny -o-z- z s z- - 3_ _ p eny m- z n -o-z- z 3 z- - n_ eny m_ n _p -o-z- z s z- - p m- z n eny -o-z z s z- - -p m-n eny _ o-r z s z- _ -p m_C(=O)NHz n eny _ o-z- z 3 r - 3-P m-~-l=~lwriz n enY
-o-z- z s z- - 3 p eny m- z n --o-z- z s z- - n_ eny m- z n _p -o-z- z s z- - m ~(=NH)NHz n me -o-z- z 3 z- - -am p- z n me _ o-z- z s z- - -am p- 2 n me _ o-z- z a z- - 3-am p-~;l=rrti)~tiz n me -o-2 2 3 2 - 3- p- z n -am - ine o-z- z s z- - n_ p- )NHz n _~
- me o-z- z s z- - i p- =O)NHz n me -o-z- z 3 z- - -am p- z n me _ o-z- 2 3 z- - -am p- z n me _ o-z- z s z- - 3-am p- =O)NHz n me - ~
o-r z 3 z- - n 3- p- =O)NHz - -am me o-z- z s z- - n n_ p- z - -am -me o-r z , z- - n eny m- z - -ammo-car oxy is acid o-5Uz Hz (:H3 LHz-~;H(-rip)-ta-Ynenyl-ammo m- z N carboxylic acid o-SUz-NHz LH3 LHz (-tin)-r-phenyl-ammo m-~(=wri)wriz LH carboxylic acid o-SUz-NHz (:H3 LHz-LH(-tin)-LH3-pnenyt-ammo m-~~=~ri)wriz carboxylic acid o-SUZ Hz LHj MHz-LH(-nn)-~H3-v-pnenyi m- z N ammo carboxylic acid o-SUz-NHz ~;H3 ~:riz-LH(-tsn)-tsn-u-pnenyi m- z ammo carboxylic acid o-~V2-NHZ LH3 LHz-LH(-tsn)-rneny-ammo m- z carooxyuc acid o-5U2-NHZ C:H3 C;H? (-tin)-(_;1-phenyl-ammo m-C:H carboxylic acid o-SUz-NHz C.;H3 c:Hz-LH(-rin)-r-pnenyi-ammo m- z carboxylic acid o-~Vz Hz (.;H3 LHz-LH(-tin)-t,ri3 m- z N pnenyt-ammo carboxylic acid o-5Vz-NHz ~;H3 LHz-LH(-tsn)-3 m- z -p eny -ammo carboxylic acid o-SUZ-NHZ C;H3 C:HZ-C:H(-tin)-n_ m- z -p eny -ammo carboxylic acid o-z- z - CH3 CHz-CH(-Bn)-a m- z y p epoxy-acetic acid ester o-z- z s z- - n a m- z - y -p enoxyacehc acid ester o-2 z 3 CHz-CH(-Bn)-Methyl m- z F-phenoxy-acetic acid ester o-~Uz-NHz c:H3 LHz (-tsn)-Mecnyi m- z c:H ~ri3-pnenoxy-acetic acid ester O-JUZ-NHZ l.Hg l.Hz (-t5n)-lVletllyl m-l.(=lVt1)1Vt12 l;H 1x13 V-pnenOXy-acetic acid ester o-JUz-NHz 1;H3 1:H2-l:H(-tin)-MeLilyl m-l:(=1Vri)iVri2 tin-v-prienOXy acetic acid ester o-~Oi-NHz CH3 CHz-CH(-Bn)-Methyl m-c:(=U)NHz Yhenoxyacehc acid ester o-z- z CH3 CHz (-Bn)-Methyl m- z CH C1-phenoxyacehc acid ester o-z- z CH3 CHZ (-Bn)-Methyl m- z CH F-phenoxyacehc acid ester o-SUz-NHz c:H3 z- - n a m- z - Y
s-P
epoxy-acetic acid ester o-SUz-NHz c:H3 LHZ (-tsn)-a m- z ~H y -P
epoxy acetic acid ester o-5Vz-NHz ~:H3 LHz-c:H(-tsn)-metnyi m- z tsn-v-pnenoxy acetic acid ester o-r z s z- - n enoxyacehc m- z - aci o-z- z s r - n -p m- z - epoxy-acetic aci o-z- z s z- - n -p m-- epoxy-acetic aci o-z- z s z- - n 3- p epoxy-aceticm-- aci o-z- z s r - n 3- m- )1VH2 - -p epoxy-acetic acid o-z- z s r - n n- m- z - -p epoxy acetic aci o-z- z s z- - n enoxyacehc m-C;(=V)NHz - aci o-z- z 3 z- - n -p m- z - enoxyacehc aci o-z- z s z- - n -p m- =O)NHz - enoxyacehc acs o-z- z 3 z- - n 3-p m- )NHz - epoxy-acetic aci o-z- z s z- n 3- m-C(=O)NHz - -p epoxy aceric acid o-z- z s z- - n n- m- z - -p epoxy acehc aci o-r z s z- n enoxye m- z - ano o-z- z 3 - z- n -p m-C(=NH~Hz - epoxy-a ano ri-z- 2 3 2- - n -p m-~~NHz - epoxy-a anol o-z- z a z- - n 3-p m- z - epoxy-a ano o-z- z s z- - n 3- p epoxy-a m-C
- - anol o-z- z s z- - n n- epoxy a m- z - -p ano z- z s z- - n enoxye m-~l=~)Nriz - ano z- 2 3 2- n -p m- z - enoxye ano o-z- z s z- n -p m-C(=O~z - epoxy-a ano o-z- z 3 z- - n s- p m-C(=O)NHz - epoxy-ethanol z- z s z- - n 3- -p m- z - epoxy-a ano o-z- 2 3 2- - n n- m-C(=O~2 - -p epoxy-a anol O-JVy-Nriz uH, ~HZ-~Hl-tin)- a m- z Y
p epoxy-a y ether O-JVZ-NHZ ~:H3 ~HZ-~Hl-tsnJ-Memyma-pnenoxyemyi m- z ether o-~u2 Hz ~:H, Ltizw;ty-tsn)-Memyi m- z N r-pnenoxy-emyi ether o-~uz-NHz ~:H3 Ltiz-~Hl-tsn)-memymai3-pnenoxy- m-~.l=mH)mHz ethyl ether o-JVZ-NHZ 1:H3 1:H2-l:Hl-tSri)-a m-Y
-p epoxy-ethyl ether o-JVz-NHz c:H3 ~;HZ sn)-nnemyi m-~l=r~H)NHz c:Hl-t tsn-V-pnenoxy ethyl ether o-5Vz-NHz c:H3 z - n a m- z - y enoxye y ether o=~Oz-NHZ -- CH3 z- - n a m- z - y -p enoxyet y ether O-5V2-NHz c:H3 z- - n a m- z - y -p enoxye y ether o-5Vz-NHZ C:H3 1;H2-C;HI-tin)-a m-Y
phenoxyethyl ether o-5VZ Hz c:H3 LHz-LHl-~sn)- nnemyi m-~l=~)Nriz N uH3-u-phenoxyethyl ether o-1Uz-NHZ l:Hg 1;H2-l:Hl-lip)- MelllY1 m-l:l=V)lVHz tin-V-phenoxyethyl ether O-JUZ-NHZ (:H3 l:Hz-l:Hl-C:Hz-pnenYi m-~l=Nri)Nriz COOCH3)-O-JUZ-NHZ 1:H3 1:H2-l:Hl-1;H2-l:l-prienYl m-l;l=1VH)1VH2 COOCH3)-O-5U2-NHZ 1:H3 1;H2-l:Hl-1:H2-r-prieriYl m-COOCH3)-O-1U2-NHZ 1.H3 l;Hz-l:Hl-1;H2-3 m-COOCH3)- p enY
o-~u2 Hz LH3 MHz-~Hl-~HZ- ~H3 m- z N COOCH3)- u-pnenyi O-JVZ-NHZ 1:H3 1;H2-l:Hl-l;Hz-tin-v-prienyl m-COOCH,)-O-JVZ-NHZ 1:H3 z- z- p m- z COOCH3)- eny o-z- z s z- z- -p m- z COOCH,)- eny O-JUZ-NHZ 1;H3 l;Hz-l:Hl-l;HZ-r-prienyl m-l;l=V)lVrlz COOCH3)-O-JUZ-NH2 1,H3 z- z- s-P m- z COOCH,)- eny O-JVZ-NHZ 3 2 2 3- m- z COOCH,)- -p eny z ~a z- r n_ u v m _p .~ v~mu o-m eny m-z-COOCH,)-o-~u2 tlz ~:ri3 taiz iz-Anllme p-~l=Nti)Nti2 N tail-t.r COOCH,)-O-JU2-Nriz ~.ri3 ~:riz-~;ril-~:ri2-~;i-anllme p-~l=ivrl)lrri2 COOCH,)-o-JUZ-Nriz 3 z- z- -am p-me COOCH3)-O-JUZ-Nriy 3 Z z- 3-am p-me COOCH3)-o-~UZ Hz ~ri3 ~ri2-aril-~ti2-Ltl3-u-anllme p-~l=Nri)Nri2 N
COOCH3)-o-JUz-NHz s r z- n- p- z -am me COOCH,)-o-JU2-NHZ lai3 z- i m p-me COOCH3)-o-5u2 Hz Ltl, ~;tiz iz-m-anllme p-N ~til-~t COOCH3)-o-JUz HZ 1x13 l;ti2-t_;tll-~;tlz-r-anllme p-N
COOCH,)-O-JUZ H2 1:ri3 lrl2-l~ril-lai2-3 p-N and me COOCH,)-o-JUz-NHz C:rl3 C:rlz-C:rtl-C:rlz-C:rij-u-amine p- z COOCH3)-O-JVZ-NHZ ~ri3 ~aiz-~ril-~ti? rsn-u-amine p-COOCH3)-o-5Vz Hz C.;tl3 ~-riz riz-eny m- z N ~-ril-L -ammo-car oxy is COOCH3)- acid o-5Uz-Nriz Ltt3 c:rlz tz-~i-rnenyl-ammo m- z call-~r COOCH3)- carboxylic acid o-5uz-NHZ c:H3 t;H2-call-cal2-r-phenyl-ammo m-COOCH3)- carboxylic acid o-SUz Hz c:H3 t;Hz-call-~tlz-3-p m- z N eny -ammo COOCH3)- carboxylic acid o-5U2-NHZ C:H3 C.:HZ-C;HI-(:HZ-1:ri3-u-Phenyl m-ammo COOCH3)- carboxylic acid o-5Uz-NHz C:H3 C:Hz iz-tsn-u-phenyl m-~l=lrrl)lvrlz (:Hl-Ca ammo COOCH3)- carboxylic acid o-5Ui HZ cal3 calz l2-rnenyl-ammo m-N t;til-Lt carnoxyllc COOCH3)- acid o-SUZ-NHz C:H3 1:H2-l:Hl-lal2-C:l-phenyl-ammo m-COOCH3)- carboxylic acid o-SUz-NHz C:H3 C:Hz-t;Hl-lalz-r-phenyl-ammo m-~l=~)lvriz COOCH3)- carboxylic acid O-JUZ-NHZ 1:H3 Cal2-l;rll-l:riZ-1:ri3 m-l.l=V)1Vt12 phenyl-amino COOCH,)- carboxylic acid o-5Uz-NHz C:H3 C:Hz-Call-C:riz-1;r13 m- z u-phenyl-ammo COOCH3)- carboxylic acid o-SUz-NHz C;H3 C:Hz-C:HI-C:Hz-tin-u-phenyl-ammo m-C:l=U)lrrlz COOCH3)- carboxylic acid o-z z 3 - CHZ-CH(-CH2-Methyl m-(:(=NH)NHZ
phenoxy-acetic COOCH3)- acid ester o-S02-NHz CH3 CHI CH(-CHz-Methyl m- z C;1-phenoxyacehc COOCH3)- acid ester o-z z CH3 CHz-CH(-CHz-Methyl m- z r'-phenoxy-acetic COOCH3)- acid ester o-2 2 3 2- z- a m-Y
s-p enoxy-COOCH3)- acetic acid ester o-~u2 HZ t;H3 ~t12-~rll-~rlzwvlemyl m-~l=l~ri)mry N ~ri3-u-pnenoxy-COOCH3)- acetic acid ester O-JU2-Nriy al3 ~ahw;ty-pry ivlemyl m-nn-u-pnenoxy COOCH3)- acetic acid ester o-z- z z- , a y enoxyacehc m- z .... z-s COOCH3)- acid ester o-SUz-NHz C:Hj CHz CH(-CHz-Methyl Cl-phenoxyacehcm-C(=U)NHz COOCH3)- acid ester o-SUz-NHz 3 CHz-CH(-CHz-Methyl F-phenoxyacehcm-C(=U)NHz COOCH3)- acid ester O-JUz-wtiz ~.ri, ~riz-~til-Ltiz-nnetnymal3-pnenoxy-m-~;l=v~~riz COOCH3)- acetic acid ester O-JUz-Nriz 3 r z- a Y 3- -P epoxy m- z COOCH3)- acetic acid ester o-~uz-Ntiz ~;ti, ~tizw;tyu;ttznnemyi tsn-u-pnenoxym- z COOCH3)- acetic acid ester o-SOz-NHz s r z- enoxyacehc aci m- z COOCH3)-o-SUz-NHz s z- r -p epoxy-acehc m- z aci COOCH3)-o-SOz-NHz CH3 CHz-CH(-CHZ r'-phenoxy- acehcm-C:(=NH)NHz acid COOCH3)-o-SOz-NHz CH3 CHz-CH(-CHz 3-p epoxy-acehc m- z aci COOCH3)-o-SOz-NHz CH3 CHz-CH(-CHz-3- -p epoxy-acehcm-C:(=NH)NHz COOCH3)- acid o-z- z CHa CHz-CH(-CHz-Bn-U-phenoxy m- z acehc acid COOCH3)-o-SOz-NHz CH3 CHz-CH(-CHz-Yhenoxyacehc m- z acid COOCH3)-o-2 z CH3 CHz-CH(-CHz-Cl-phenoxyacehc m- z acid COOCH3)-o-S~P ITi- CH3 CHz-CH(-CHz-1'-phenoxyacehc m-C;(=U)NHz acid COOCH,)-o-z- z CH3 CHz-CH(-CHz-CH3-phenoxy-acehcm- z acid COOCH3)-o-z- z CH3 CHz-CH(-CHz-CH3-U-phenoxy m- z acehc COOCH,)- acid o-z- z CHs CHz-CH(-CHz-Bn-U-phenoxy m- z acehc acid COOCH3)-o-SUz-NHz C;H3 C:Hz Hz-enoxye ano m- z c:Hl-L
COOCH3)-o-SUz-NHz C;H3 z r -p epoxy-a ano m- z COOCH,)-o-z- z s z- z- -p epoxy- a ano m- z COOCH3)-o-SUz Hz cai3 t;tiz-pail-~;tiz-3-p epoxy-a ano m- z N
COOCH3)-o-SUz-NHz c:H3 caiz-l;tilWtizW;ti3-u-pnenoxy-emanoim- z ;
COOCH3)-o-SUz-NHz C:H3 r z n- -p epoxy a m- z ano COOCH3)-o-SUz-NHz c:H3 ~tiz-aril-~riz-enoxye ano m- z COOCH3)-o-SUz-Nriz c:H3 Ltlz-call-Ltlz-c:1-pnenoxyemanoim- z COOCH,)-o-SUz-NHz C;H3 c:Hz-~;Hl-LHz-r-pnenoxy-emanoim- z COOCH,)-o-SUz-NHz C:H3 C;HzW i? 3-p epoxy-a ano m- z :Hya COOCH3)-o-SUz-NHz (:H3 c:Hz riz-Lns-u-Pnenoxy- m- z Cail-~ emanoi COOCH3)-o-SUz-NHz c:H3 c:Hz-Ltil-Ltiz-tsn-u-pnenoxy- m- z emanoi COOCH3)-O-SUZ-NHZ c:H3 c:Hz-Ltil-Ltiz-Merry pnenoxy-emyim- z COOCH3)- ether o-z- z CH3 z- z- a y -p enoxye m- z y COOCH3)- ether o-~uz-Nriz ~n3 ~riz-~ry-~ry-nnecnyi r-pnenoxy-emyim-~l=ivriJNriz COOCH3)- ether o-~uz-Nriz Sri, ~riz-aril-~ri2 nnetnyi ~ri3-pnenoxy-m-~l=NriJNriz COOCH3)- ethyl ether o-~uz-Nttz ~ri3 ~riz-~til-~tiZ memyi ~ti3-u-pnenoxy-m-~;l=NriJNtiz COOCH3)- ethyl ether O-JUZ tiz uri3 uriz-aril-utiz-Memyi isn-u-pnenoxym-ul=Nri)Ntiz N
COOCH,)- ethyl ether O-JVz-Nriz ~ri3 ~riz-aril-~riz-enemy rnenoxyemym-~l=u)Nriz COOCH,)- ether O-JVZ-Nriy ;rij ~;riz-aril-~riz-nnemyi m-pnenoxyemyim-~l=uJivriz COOCHj)- ether O-JVZ-lVri2 ~-ri3 Lri2'~-ril'~-riz-nnetnyi r-pnenoxyewyim-~:l=uJNriz COOCH3)- ether O-JUz-Ntiz ~ri3 ~riz-aril-~riz Metnyi ~ri3- m- z COOCH,)- phenoxyethyl ether o-~uz-Nttz ~ti3 ~aiz-aril-~tiz-Memyi ~rij-V- m- z COOCH3)- phenoxyethyl ether o-z- z s z- 2 a y n-m m m v-COOCH3)- phenoxyethyl ether O-JVz-ivtiz ~;ri3 ~aiz-~atl-~:riz-pnenyi m-~.l=mnyvriz CHz-OH)-O-~Uz-Nriz s z- z- -p eny m- z CHz-OH)-O-JUZ-Nt12 liri3 1;ri2-l;ril-1:ri2-r-pnenyi m-~:l=ivri)ivriz CHz-OH)-O-JUz-Nriz ~ri3 ~riz-aril-~riz-3-p eny m- z CHZ OH)-O-JUZ-iVriz ~ti3 ~riz-~ril-~riz-~ri3-u-pneny m- z CHz-OH)-O-~Uz-Nriz uri3 urtz-aril-uriz-isn-u-pnenyi m-~l=ivri)ivriz CHz-OH)-O-JUZ-NriZ Lti3 ~tiz-~til-~ri2 pnenyi m-~.l=uJivriz CHz-OH)-O-JUz tiz ~ti3 ~iiz-c:ril-~riz-m-pnenyl m- z N
CHZ OH)-o-~Vz-Nrlz ~r13 ~riz-~rll-~rlz-r-pnenyi m- z CHz-OH)-O-JUy-NriZ ~ai3 ~aiz-~til-~ri2-~:ri3-pnenyi m- z CHz-OH)-o-~uz-Ntiy ai3 z- z- 3- -p eny m- z CHz-OH)-O-~Uz-Nriz ~ri3 ~riz-aril-~tiz-n_ _p eny m- z CHz-OH)-o-JUZ-Nrtz 3 z- r m me p-CHz-OH)-o-~Uz-tvtiz s z- r -am me p- z CHz OH)-o-JUZ-iVrlz ~ri3 ~ri2-pry-~ri2-r-amime p-~l=ivriJivriz CHz-OH)-o-JUZ-lVr12 1:r13 2- z- 3-am me p-CHz-OH)-O-JVz-Nriz , z- z- 3 -am me p- z CHz-OH)-o-~UZ ttz url3 uriz-urll-ur1z isn-u-amlme p-~l=NriJNnz N
CHz-OH)-O-JUZ-iVr12 1x13 uri2-aril-uriz-Amime p-ul=vyvriz CHz-OH)-o-~uz-Niiz ~ti3 ~aiz-aril-~:riz-t,i-amnne p-t.l=v)ivriz CHz-OH)-z- 2 3 2- z- -am me ..
p-CHz-OH)-o-SUz-NHz C.:H3 (:Hz-C;H(-C:Hz-C:H3-anllme p-l:(=U)iVriz CHz-OH)-o-SUz-NHz s z- z- 3 p- z -am me CHz-OH)-o-SUz-NHz s i z- n- p- z -am me CHI OH)-O-SUZ-NHz C:H3 l;Hz Hz-eriy m- z l;H(-l: -ammo-car Oxy CHz-OH)- acid o-SUz-NHz c:H3 LHz t;H(-t;Hz-Li-rnenyi-ammo m- z CHz-OH)- carboxylic acid O-5Uz-NHz ljH3 (:Hz riz-r-pnenyi-ammo m-l:H(-l CHz-OH)- carboxylic acid O-5Uz-NHz 1;H3 (:Hz-l;H(-l;Hz C;H3-pnenyi-ammo m- z CHz-OH)- carboxylic acid o-5Uz-NHz C:H3 l:Hz-C:H(-l:Hz-c:H3-u-pnenyi m- z ammo CHz OH)- carboxylic acid o-SUz-NHz ~:H3 ~:Hz-LH(-~:Hz-tsn-u-pnenyi m- z ammo CHz-OH)- carboxylic acid o-5Vz-NHz C:H3 C;Hz-l:H(-l:Hz-Ynenyi-ammo m-l:l=U)lVriz CarbOXyllC
CHz-OH)- acid o-5uZ Hz c:H3 LHZ c:H(-LHz-m-pnenyi-ammo m- z N
CHz-OH)- carboxylic acid o-JVz-Nriz Lti3 MHz c:H(-MHz-r-pnenyi-ammo m-~l=~yvriz CHz OH)- carboxylic acid o-5uz-NHz c:H3 ~Hz-c:H(-MHz ~H3-pneny-ammo m- z CHz-OH)- carboxylic acid O-5Uz-NHz (:H3 l;Hz Hz 1:ri3-V-pneriyi-ammo m- z C.;H(-l;
CHz-OH)- carboxylic acid o-JVz-NHz (:H3 l;Hz-C;H(-l;Hz-tan-u-prieriyi-ammo m- z CHz-OH)- carboxylic acid o-z z ; BIZ-CH(-CHz Methyl m- z phenoxy-acetic CHz-OH)- acid ester o-r z s CHz CH(-CHz-a m- z y -p enoxyacehc CHz-OH)- acid ester o-z- z s CHz-CH(-CHz-Methyl m- z F-phenoxy-acetic CHz-OH)- acid ester o-JVZ Hz 1;H3 l;Hz-l;tl(-1;ri2lVleTnyi m- z N 1;r13-pnenOXy-CHz-OH)- acetic acid ester .
O-JVz-Nriz c:H, MHz c:H(-MHz-ivietnyi m- z ~ryu-pnenoxy-CHz OH)- acetic acid ester o-5Uz-NHz c:H3 ~:Hz-LHIw:Hz-Merry m-~(=tvryvriz tsn-u-pnenoxy CHi OH)- acetic acid ester o-SOz-NHz CH3 CHz-CH(-CHz-Methyl m-(:(=U)NHz Yhenoxyacehc CHz-OH)- acid ester o-z- z CH3 CHz-CH(-CHz Methyl m- z Cl-phenoxyacetic CHz-OH)- acid ester o-z- z s CHz CH(-CHz-Methyl m- z F-phenoxyacetic CHz-OH)- acid ester o-~u2 Hz c,H, uHz-c:ri(-uriz-Merry m-~t=u~wriz N ~ri3-pnenoxy-CHz-OH)- acetic acid ester o-r z s z- z- a m- z Y
-p epoxy CHz-OH)- acetic acid ester o-DUz-NHz c:H3 ~aiz-cai(-Ltizivietnyi m-~~=uyvriz nn-u-pnenoxy CHz-OH)- acetic acid ester o-2 z CH3 CHz-CH(-CHz-Phenoxyacetic m-C(=NH)NHZ
acid CHz-OH)-o-OZ-NH2 CH3 CHz CH(-CHz-Cl-phenoxy-acetic m-C(=NH)NHz acid CHz-OH)-o-r 2 3 z- z- -p m- )NHz epoxy-acetic aci CHz-OH)-o-z- z LHs z- z- 3-p enoxy-aceticm- z aci CHz-OH)-o-SUz-NHz 3 (:Hz-(:H(-C;Hz-(:H3-U-phenoxy-aceticm-C;(=NH)NHz CHz-OH)- acid o-SUz-NHz ~ C;H2 Hz-13n-U-phenoxy m-(:(=NH)NHz LH(-(: acetic acid CHz-OH)-o-SVz-NHz j C:Hz-C;H(-C:Hz-Yhenoxyacehc m-(_:(=U)NHz acid CHz-OH)-o-5Uz-NHz 3 C;Hz Hz-(:I-phenoxyacehcm-C:(=U)NHz C;H(-L acid CHz-OH)-o-5Uz-NHz s z z- -p enoxyacehc m- z aci CHz-OH)-o-~Uz-NHz C;H3 C:Hz-C:H(-C;HZ C;H3-phenoxy-aceticm-C:(=U)NHz acid CHz-OH)-o-SUz Hz C;H3 r r 3- -p enoxy aceticm- z N
CHz-OH)- acid o-SUz-NHz C;H3 (:Hz-C:H(-C;Hz-tan-U-phenoxy m-C:(=U)NHz acetic acid CHz-OH)-O-JVz-wriz ~ri3 z- z- enoxye ano m- z CHz-OH)-O-JVz-wriz uri3 uriz-aril-uriz-m-pnenoxy-emanoim-ul=wrywriz CHz-OH)-o-~uz-Nry uns ~-nraril-~-na-r-pnenoxy- emanoim-ul=wrywriz CHz-OH)-o-~uz-Ntiz t,ti3 ~aiz-t.;til-~tiz-tai3-pnenoxy-emanoim-~:l=mtyvriz CHZ OH)-O-JVZ riz uri3 ~nz-aril-uriz-url3-u-pnenoxy-emanoim-~l=NriJwriz w CHz-OH)-o-~uz-Nriz uns urirunl-~nr ~sn-u-pnenoxy m-ul=wrywtiz emanoi CHz-OH)-O-JU2-Nriz uri3 uriz riz-rnenoxyemanoi m-ul=ulwriz ury-~
CHz-OH)-o-auz-lVtiz Lti3 ~riz-~nl-~riz-~l-pnenoxyemanoim- z CHz-OH)-o-z- z s z- z- -p enoxy-a ano m- z CHz-OH)-o-z- 2 3 2- z- s-p enoxy-a ano m- z CHz-OH)-o-JIJZ-iVriz l.rig l.rlZ-l.rll-1.r12-~:ri3-u-pnenoxy-m-~.l=uyvnz emanoi CHz-OH)-O-JVz-lVriz Lti3 r r n- -p enoxy- m- z a ano CHz-OH)-O-JVz tiz pry z- z- a y p enoxy-a m- z w y CHz-OH)- ether O-JVz ttz ~rij ~riz-aril-~rizMetnyi m-pnenoxyemyim- z N
CHz-OH)- ether o-~uz-Ntiz t_;ti, unz-~nl-unz-Merry r-pnenoxy-emyim- z CHz-OH)- ether O-JVZ-Ntiz jai, t.riz-~:ril-~;riz-Memym;rij-pnenoxy-m-t.l=mryvriz CHz-OH)- ethyl ether O-JUz-lVriz ~:ri3 ~-nz-~-ril-~-nr Memym-ri3-v-pnenoxy-m-Ll=lVt1)lVrlz CHz-OH)- ethyl ether O-JUZ-1Vt12 Lti3 unz-unl-~nz-Merry rsn-u-pnenoxym-ul=wrywriz CHz-OH)- ethyl ether o-JUz-1Vt12 ~ri3 ~r12-~rll-~ri2-Merry rnenoxyemyim-~l=u~Nriz CHz OH)- ether O-JUz tiz uri3 uriz-uril-~riz-Merry m-pnenoxyetnym-ul=u~wtiz w CHz-OH)- ether O-JUz-wtiz ~ti3 uriz-uril-~nz-Merry r-pnenoxyemyim-ul=u~wriz CHz-OH)- ether o-~u2 riz cai3 utiz-aril-utiz-Merry uri3- m-ul=u~wriz w CHz-OH)- phenoxyethyl ether o- z- z ns z- z- a Y 3 m- z CHz-OH)- phenoxyethyl ether O-JUz-Nrl2 t,ri3 ~;riz-jai(-~;tizMetnyi tsn-u- m-~(=u~wtiz CHz-OH)- phenoxyethyl ether O-JUz-iVri2 ~:ri3 ~tiz-t_;rs(-~:riz-pnenyi m-~:(=mtyvtiz C(=O)-N-morpholino)-O-JUz-Nriz ~ri3 ~riz-Sri(-~riz-m-pnenyi m-~(=wri~Nriz C(=O)-N-morpholino)-O-JUz-Nriz ~;ri3 ~riz-t,ri(-~riz-r-pneny m-~,(=mryvriz C(=O)-N-morpholino)-o-~uz-Ntiz Lti3 Ltiz-~;ti(-Ltiz-t_ai3-pnenyi m-~;(=mrywriz C(=O)-N-morpholino)-o-JUz-Ntiz url3 ~rtz-ur1(-~rlz-uri,-u-pneny m-~(=wrywriz C(=O)-N-morpholino)-o-~Uz-Ntiz Lti3 Ltiz-t,ti(-Lri2tsn-u-pnenyi m-~(=mriyvriz C(=O)-N-morpholino)-O-JUZ-Ntl2 Lti3 Ltiz-~:ri(-Ltiz-pnenyt m-~.(=a yvriz C(=O)-N-morpholino)-o-JVz 1Vt12 (a13 (:rlz-tJr1(-~alz-tri-pnenyi m-t,(=uyvtiz C(=O)-N-morpholino)-o-5V2-Nri2 Lti3 t;tiz-~;ti(-~;tiz-r-pnenyi m-~(=uyvriz C(=O)-N-morpholino)-O-JUZ-Ntl2 lai3 1x12-l;ri(-1;t12-lal3-prieriyl m-l:(=u)lVtlz C(=O)-N-morpholino)-o-~uz-Ntiz jai, ~;riz-tai(-~;tiz-~:n3-u-pnenyi m-L(=uJlvriz C(=O)-N-moipholino)-O-JUz-lVri2 Lti3 Ltiz tayu;tizrsn-u-pnenyi m-~.(=uyvriz C(=O)-N-morpholino)-O-JUZ-Nri2 Lri3 ~tiz-uri(-urizAmime p-~(=wrywriz C(=O)-N-morpholino)-O-JUZ-1VY12 (..Y13 l,rl2-l.rl(-l.rlz-L;~-an111l1e p-l.(=lVt1)lVri2 C(=O)-N-morpholino)-O-JUZ-Nti2 Lti3 ~ttz-uri(-~tiz-r-amime p-~(=wti~wriz C(=O)-N-moipholino)-O-JUz-Ntl2 l;tig l:riz l;rl(-1x12-l:rlg-amllrie p-L(=lvri)lvriy C(=O)-N-morpholino)-o-~uz-Ntiz cai3 uriz-uri(-~riz-~ri3-u-amime p-~(=wryvriz C(=O)-N-morpholino)-O-JUZ-Nrl2 Lti3 ~;tiz-~:ri(-t,tiz-tsn-u-amime p-~;(=mryvriz C(=O)-N-morpholino)-o-~uz-Ntiz ~ri3 uriz-Sri(-~riz-Amime p-~(=u~wriz C(=O)-N-morpholino)-n- z- 2 3 2- r -am me p- NHz = 221 -moipholino)-O-JVz-Nriz ~.ri3 ~riz-aril-~riz-r-amime p-~l=u)mriz C(=O)-N-morpholino)-o-JUz-Nriz ~ri3 ~riz-aril-~riz-~ti3-amime p-~.:1=u)Nriz C(=O)-N-morpholino)-o-auz-Ntiz ~:ri3 ~riz-aril-~riz-uri3-u-amime p-~l=u)wriz C(=O)-N-morpholino)-O-JUz-Nrlz 1:ri3 l:riZ-l;tll-lalz-lin-u-amllrie p-l:l=u)lVrlz C(=O)-N-morpholino)-O-JUz-LVtlz ~-ri3 ~-ri2-~-ril-~-riYrneny-ammo-carooxyucm-~;l=wti)wtiz C(=O)-N- acid morpholino)-O-JUZ-lVtlz 1:r13 Lri2-Lril-Lri2-l.l-Ynenyl-amlIlOm-l.l=lVr1)lVtiz C(=O)-N- carboxylic acid morpholino)-O-JUz-lVtiz 1;r13 ~aiz-~:ril-~:riz-r-pnenyi-ammo m-~:l=ivri)ivriz C(=O)-N- carboxylic acid morpholino)-O-JVz-NHz ~ai3 ~:rtz-pail-~aiz-~-n,-pnenyi-ammom-~;l=ivri)wriz C(=O)-N- carboxylic acid moipholino)-O-JUz-Nriz ~:ri3 t,riz-t,ry-~ry-t,ri,-u-pnenyi m-~.l=ivri)ivriz ammo C(=O)-N- carboxylic acid morpholino)-o-JVz-NHz llri3 ~;riz-pail-Ltiz-tsn-u-pnenyi m-~;l=ivri)ivriz ammo C(=O)-N- carboxylic acid morpholino)-O-JUz NHz l.ri3 l;tlz-l:ril-l:tlZYnenyl-ammo CarDOXyIICm-l:l=u)lVrlz C(=O)-N- acid morpholino)-o-JUz-Nriz ~;ti3 ~:rtz-~;til-~tiz-ta-pneny-ammo m-~l=u)mriz C(=O)-N- carboxylic acid morpholino)-o-JUz-Nriz uri3 urtz-~:ril-~riz-r-pneny-ammo m-~l=u)wriz C(=O)-N- carboxylic acid morpholino)-O-JVz-lVriz 1:ri3 1;ri2-l;ril-l:riz-~:ri3-pnenyi-ammom-~:l=u)ivriz C(=O)-N- carboxylic acid morpholino)-O-JUz-Nriz Lri3 ~aiz-~-ttl-Lriz-~n3-~-Pneny-ammom-~;l=u)ivriz C(=O)-N- carboxylic acid morpholino)-o-~uz-Ntiz uri3 uriz-aril-~riztsn-u-pnenyi-ammom-~l=u)ivriz C(=O)-N- carboxylic acid morpholino)-o-SOz-NHz CH3 CHz-CH(-CHz-Methyl phenoxy-aceticm-(:(=NH)NHz C(=O)-N- acid ester morpholino)-o-SOz-NHz CH3 CHz-CH(-CHzMethyl Cl-phenoxyacehcm-C(=NH)NHz C(=O)-N- acid ester morpholino)-o-SOz-NHz CH3 CHz-CH(-CH2Methyl r'-phenoxy-m-C(=NH)NHz acetic C(=O)-N- acid ester morpholino)-o-~uz-Ntiz uri3 urir~-ril-~nz-MemYi ~-n3-pnenoxy-m-l~l=lVr1)lvri2 C(=O)-N- acetic acid ester morpholino)-o=S~ CH3 z- z- a y 3- -p enoXy=-m-~N-- Hz C(=O)-N- acetic acid ester morpholino)-O-JUz-mriz ~:ri3 ~aiz-pail-Lti2Memyi nn-u-pnenoxym-~;l=NtyNtiz C(=O)-N- acetic acid ester morpholino)-o-SOz-NHz CH3 CHz-CH(-CHz-Methyl Phenoxyacehcm-C(=U)NHz C(=O)-N- acid ester morpholino)-o-SOz NHz CH3 CHz-CH(-CHz-Methyl Cl-phenoxyaceticm-C(=U)NHz C(=O)-N- acid ester morpholino)-o-SOz-NHz CH3 CHz-CH(-CHz-Methyl l~-phenoxyacehcm-C(=U)NHz C(=O)-N- acid ester morpholino)-o-auz-Nriz ~ri3 ~ri2 aril-~riz-memym;rij-pnenoxy-m-~l=u~rrriz C(=O)-N- acetic acid ester morpholino)-O-JVZ-NHZ Lti3 caiz-~ry-~ry-nnemyi ~ri3-u-pnenoxym-~l=u~wriz C(=O)-N- acetic acid ester morpholino)-O-JVZ-NHZ Lti3 ~tiz-~til-~tiz-Memyi tsn-u-pnenoxym-~l=u~wriz C(=O)-N- acetic acid ester morpholino)-o-SOz-NHz CH3 CHz-CH(-CHzPhenoxyacetic m-C(=NH)NHz acid C(=O)-N-morpholino)-o-SOz-NHz CH3 CHz-CH(-CHz-Cl-phenoxy-aceticm-C:(=NH)NHz acid C(=O)-N-morpholino)-o-SOZ NHz CH3 CHz-CH(-CHz-F-phenoxy- aceticm-C(=NH)NHz acid C(=O)-N-morpholino)-o- z- z CH3 CHz-CH(-CH2CH3-phenoxy-aceticm-C(=NH)NHz acid C(=O)-N-morpholino)-o- z- z CH3 CHZ CH(-CHz-CH3-O-phenoxy-aceticm-C(=NH)NHz C(=O)-N- acid morpholino)-o- Oz-NHZ CH3 CHz-CH(-CHZBn-U-phenoxy m-(:(=NH)NHz acetic acid C(=O)-N-morpholino)-o- z- z CH3 CHz CH(-CHz-Phenoxyacetic m-C(=U)NHz acid C(=O)-N-morpholino)-o- z z CH3 CHz-CH(-CHz-Cl-phenoxyacehc m-C(=U)NHz acid C(=O)-N-morpholino)-o-SOz NHz CH3 CHz-CH(-CHz-r'-phenoxyacehc m-C(=U)NHz acid C(=O)-N-morpholino)-o-~O~ NHZ CH3 CHz-CH(-CHz-CH3-phenoxy-aceticm-C(=U)NHz acid C(=O)-N-morpholino)-o- z- z s CHz-CH(-CHzCH3-U-phenoxy m-C(=U)NHz acetic C(-0)-N- acid morpholino)-o-SOz-NHZ CH3 CHz-CH(-CHz-13n-U-phenoxy m-(:(=U)NHz acetic acid C(=O)-N-morpholino)-o-JUz-Nriz 3 z- z- enoxye ano m- z C(=O)-N-more o mo -o-~uz-rVriz ~ri3 ~riz-~ry-~tiz-Li-pnenoxy-emanoim-~l=NryNtiz C(=O)-N-morpholino)-O-JUz-Nriz ~ri3 ~riz-aril-~riz-r-pnenoxy- emanoim-~:l=mtiyvtiz C(=O)-N-morpholino)-O-JUz-wriz ~ri3 ~riz-aril-~riz-uri3-pnenoxy-emanoim-~;l=r~riJwriz C(=O)-N-morpholino)-O-JUz-wriz ~r13 ~:rizw:ry-~tiz-~r13-u-Pnenoxy-emanoim-~.~=mryrVriz C(=O)-N-morpholino)-o-JUz-Nriz ~:ri3 ~:rlz-call-~tiz-tsn-u-pnenoxy m-~:~=mryrrriz emanoi C(=O)-N-morpholino)-O-JUZ-lVYlz Lri3 ~'ri2-Lril-Lri2-rnenoxyemanoi m-~~=uyvriz C(=O)-N-morpholino)-o-~uz-Ntiz ~ri3 uriz-~ry-~riz-~i-pnenoxyemanoim-~~=ulwriz C(=O)-N-moipholino)-o-~Vz-lvriz Lri3 Lnz-unl-unrr-pnenoxy-emanoim-~l=u~wriz C(=O)-N-morpholino)-o-~u2 NHz Lti3 ~;ttz ~;ril-Ltiz-~ai3-pnenoxy-emanoim-~l=uJmriz C(=O)-N-morpholino)-O-JUz-Nrlz urij utiz-aril-uriz-~ri3 u-pnenoxy- m-~l=a ~wriz emanoi C(=O)-N-morpholino)-O-JUz-Nrl2 uric unz-uril-~nz-~n-u-pnenoxy- m-~~=u~rrriz emanoi C(=O)-N-morpholino)-o-~Vz-Nriz t;ti3 Lriz-Ltil-utiz-nnemyi pnenoxy-emyim-~~=wrywtiz C(=O)-N- ether morpholino)-o-5Uz-NHz t;ri3 caiz-Ltil-LtizMemyi m-pnenoxyernyim-~l=wri~rrriz C(=O)-N- ether morpholino)-o-JUz-NHz cai3 ~:rizway-Ltiz-enemy r-pnenoxy-emym-~:~=mryvriz C(=O)-N- ether morpholino)-o-~u2 lvtiz t;ti3 Lry~til-~riz-nnemyi ~ri3-pnenoxy-m-~l=mryvriz C(=O)-N- ethyl ether morpholino)-o-JUz-Nriz c:rl3 ~riz-pail-~riz-enemy ~ri3-u-pnenoxy-m-~~=ivryvriz C(=O)-N- ethyl ether morpholino)-O-~Uz-Nriz Lti, utiz-aril-uriz-Memyi tsn-u-pnenoxym-~~=wryvriz C(=O)-N- ethyl ether morpholino)-O-~Vz-Nriz t;ti3 ~riz-~rll-~rlz-Memy rnenoxyetnym-~l=u~rVriz C(=O)-N- ether morpholino)-o-auz-Nriz ~ti3 ~riz-~ry-~rizMemy m-pnenoxyemym-~~=uyvriz C(=O)-N- ether moipholino)-O-~Uz-Nrlz Lti3 Ltiz-~til-~tiznnemyi r-pnenoxyemyim-~l=uyvmz C(=O)-N- ether moipholino)-o- 2 2 3 2- r a Y s- m- z p enoxyet y a er morpholino)-O-JVZ lVtlz 1.ri3 l:riz-l.;tl(-l.rlz-Memyl l.rl3-V- m-l.~=V)1Vr12 C(=O)-N- phenoxyethyl ether moipholino)-O-JUz-mtiz 1Jr13 l:riz-t,ri(-t,tiz-iviemyi tsn-u- m-~;(=Vyvtiz C(=O)-N- phenoxyethyl ether morpholino)-o-JVZ Ntlz Calj l:tlz-Cal(-Calz-phenyl m-l:(=Nti)Ntlz CHz-S(O)z-CH, O-JVi Nriz j l:riz-Sri(-l:riz-la-pnenyi m-~(=wri)Nriz CHz-S(O)z-CH, O-wz-ivtiz t,rl3 l;riz-tai(-t_;tiz-r-pnenyi m-~;(=wrywriz CHz-S(O)Z
o-~u2-Nriz 1a1, laiz-Sri(-l:riz-1;r13 pnenyi m- z CHz-S(O)z-CH3 O-JUz-Nriz jai, l:riz-l:ri(-l:riz-1:r13 u-pnenyi m- z CHz-S(O)z-CH3 o-JUZ-Nriz s z- z- n- -p eny m- z CHz-S(O)z-CH3 o-JVZ-Nri2 1x13 lain lai(-laiz-pneny m-~~=Vyvriz CHz-S(O)Z
o-JVz-NriZ l:ri3 z- z- -p eny m- z CHz-S(O)z-CH3 O-JVZ-Nriz 1x13 z' Y -p eny m- z CHz-S(O)z-CH3 o- z- z a z- z- s-p enY m- z CHz-S(O)z-CH3 o-JUZ-Nri2 t;ti3 laiz-t;ti(-t_;tiz-3- -p eny m- z CHz-S(O)2 o-~uz-Ntiz 1:r13 l:riz-l:ri(-l:riz-rsn-u-pnenyi m- z CHz-S(O)z-CH3 o-~u2 Ntlz 1:ri3 z- z- m me p- z CHz-S(O)z-CH3 o-JVz Ntiz 1:ri3 Cain lai(-lai2-l:l-aI111me p-CHz-S(O)z-CH3 o-JU2-Ntl2 1.113 1.112-l.rl(-l.rl2-r-amlme p-l:~=lVr1)lvrl2 CHz-S(O)rCH3 O-JV2-Nriz 1x13 l:riz-l:ri(-l:riz-1:r13-amnne p- z CHz-S(O)z-CH3 o-~uz-Ntiz t_;ti3 l:riz-l:ri(-laiz-1:r13-u-amime p- z CHz-S(O)z-CH3 o-JUz-Nriz (_a13 laiz-lai(-laiz-tin-u-anllme p- z CHz-S(O)z o-JUz-Ntiz lai3 z' z- m me p-CHz-S(O)z-CH3 o-JVZ-Ntl2 s z- z- -ani me p-CHi S(O)z-CH3 o-1Uz-Nti2 1x13 1x12-Cal(-lalz-r-amlme p-l;(=u)iVrlZ
CHz-S(O)z-CH3 o-JUz Nti2 C:rig 1x12-l;ti(-1x12-1x13-amlme ~ p- z CHz S(O)z-CH3 O-JUZ-Ntiy laig 1:ri2-l;rl(-1;r12-l:rlg-u-anllme p-CHz-S(O)z-CH3 O-lUz-Ntiz 1x13 l;ti2-l:rl(-1:r12-tSn-u-arillme p- y CHz S(O)z-CH, o-JU2-Ntl2 1x13 lalz-lal(-1;ri2-Yrienyl-ammo-CarDOXyIICm-l:(=lvrl)1vt12 CHz-S(O)2 acid CH, O-JUZ-Ntl2 1;113 1x12-lal(-1~t12-l.l-Ynenyl-ammo m-l.(=lVt1)iVrlz CHz-S(O)2 carboxylic acid o-JVz Ntlz 1;t13 l;riz-lal(-lain-r-pnenyl-ammo m-l;(=lVr1)1Vr12 CHz S(O)z-CH3carboxylic acid CH3 z- z- 3-p m-C(=~)~z .~ .,.. eny o- z- z -amino -,.~.
..
CHz-S(O)z-CH3carboxylic acid o- z- z 3 z- z- 3- m- z -p eny ammo CHz S(O)z-CH3carboxylic acid O-JVz-Nriz ~:ri3 ~;riz-Lrll-Lrlz-tsn-u-pnenyl m-~;l=rVryl~riz ammo CHz-S(O)z-CH3carboxylic acid o-JVz-Nriz s r r eny m- z -ammo car oxy is CHz-S(O)z-CH,acid o-~Vz-Nriz ~ri3 ~ti2 ~Hl-~tiz-m-pneny-ammo m-~l=~~Nriz CHz-S(O)z carboxylic acid o-at~z NHz ~ri3 ~tiz-aril-~tiz-r-pnenyi-ammo m- z CHz-S(O)z carboxylic CH3 acid o-JVz Ntiz c:ri3 ~tiz ~til-~ttz-~ri3-pnenyi-ammo m-~l=~~Nriz CHz-S(O)z-CH3carboxylic acid O-JVz-Nriy 1:r13 l:riz-tall-1:ri2-~ai3-v-pnenyi-ammo m-~;l=vJ~riz CHz S(O)z-CH3carboxylic acid O-JVZ-Nriz ~ri3 ~riz-~til-catz-tin-v-pnenyi-ammo m-~l=v~~riz CHz-S(O)z-CH,carboxylic acid o-SOz-NHz CH3 CHz-CH(-CHz-Methyl m-C(=NH)NHz phenoxy-acetic CHZ S(O)2 acid CH3 ester o-SOz-NHz CH3 CHz-CH(-CHz-Methyl m-C(=NH)NHz Cl-phenoxyacehc CHz S(O)z-CH3acid estei o-SOz-NHz CH3 CHz-CH(-CHzMethyl m-C(=NH)NHz l~-phenoxy-acetic CHz-S(O)z-CH3acid ester z- 2 3 2- z- a m- z Y
a-P
epoxy-CHz-S(O)z-CH3acetic acid ester O-JUZ-NH2 c:H3 ~aiz-pail-caizMetnym;ti3-u-pnenoxy- m-~:l=rrrywriz CHz S(O)z-CH3acetic acid ester o- r z s z- z- a m- z y n--p epoxy CHz-S(O)z acetic CH3 acid ester o- 2 NHz CH3 CHz-CH(-CHz-Methyl m-C(=U)NHz Yhenoxyacehc CHz-S(O)z-CH3acid ester -NHz CH3 CHz-CH(-CHz-a m- z y -p enoxyacehc CHz S(O)z acid CH3 ester o-SUz-NHz CH3 CHz-CH(-CHz-a m- z y -p enoxyacehc CHZ S(O)z acid CH3 ester O-JUZ-NHZ cal3 ~:Hz-LH(-LHz-nnemymai3-pnenoxy- m- z CHz S(O)z acetic CH3 acid ester O-JVz-1VH2 Lti3 ~:riz-aril-~tiz-memym:ri3-u-pnenoxy m- z CHz-S(O)z-CH3acetic acid ester o-~uz-NHz ~ri3 ~riz-~ry-~riz-enemy m- z rsn-v-pnenoxy CHz-S(O)z-CH3acetic acid ester o-SUz-NHz CH3 CHz-CH(-CHz-Yhenoxyacehc m-C;(=NH)NHz acid CHz-S(O)z-CH3 o-SOz-NHz CH3 CHz-CH(-CHz-CI-phenoxy-acetic m- z acid CHz-S(O)z o-SOz NHz CH3 CHz CH(-CHz-H-phenoxy- m- z acetic acid CHz S(O)z o-SOz-NHz CH3 CHz-CH(-CHz-CH3-phenoxy-acetic m- z acid CHz-S(O)2 o- z-NHz CH3 CHz-CH(-CHz-CH3-U-phenoxy-acetic m- z CHz-S(O)z-CH,acid o-SUZ-NHz CH3 CHz-CH(-CHz-n- m- z -p epoxy acetic aci CHz-S(O)2 o-SOZ NHz CH3 z- z- enoxyaceric m- z aci CHz-S(O)z-CH3 o-SOZ-NHz CH3 z- z- -p m- z enoxyacehc aci CHz-S(O)z-CH3 -o-SOZ NHZ CH3 z- z- -p m- z -- enoxyacetic aci CHz-S(O)z-CH3 z- z s z- z- 3 m- z p epoxy-aceric aci CHz-S(O)2 CHs o-z- z LH3 z- z- 3- m- =U z -p enoxy acetic CHz-S(O)z-CH,acid o-5Uz-NHz C:H3 (:Hz-C;H(-C;Hz-Bn-U-phenoxy m-(:(=U)NHz acetic acid CHz-S(O)i CHj O-JVZ-lVri2 3 ~-rii unl-unz-rnenoxyemanol m-l:l=Nrywriz CHz-S(O)z-CH3 O-JUz-lVrlz 3 l:rlz-c.;tll-lalz--p m- z enoxy-a ano CHz-S(O)z CH, O-JUz-Nri2 s z- r -p m- z enoxy-a ano CHz-S(O)z-CH3 o-~uz-Nriz 3 z- z- 3-p m- z enoxy-a ano CHz-S(O)z-CH3 o-~uz-lvHz lal3 Ltlz-fall-l:tlz-cai3-u-pnenoxy-ethanol m-l:l=Nttyvri2 CHz S(O)z-CH3 O-~Vz-lVriz lai3 Lriz-Lril-Lriz-~sn-v-pnenoxy m- z emanol CHz S(O)z-CH3 O-JUZ-iVt12 1x13 1x12-fall-1x12-YnenOXyeman0l m-l:l=u)lVri2 CHz-S(O)z-CH3 o-~uz-lvHz lai3 lalz-lay-tay-1;1-pnenoxyetnanol m- z CHz-S(O)z-CH3 O-JUz-lVtlZ 1;H3 1a12-lall-l;riz-r-prieriOXy-ethanol m-l:l=V)lVtlz CHz-S(U)z-CHj O-~u2-Ntiz 1x13 l:riz l:ril-1;ri2-3-p m-enoxy-a ano CHz-S(O)z-CHj o-JVz tiz 1:H3 l;tlz l;til-1:ri2-1:ri3-V-pnenOXy- m- y N elllanol CHz-S(O)z-CH3 o-JVy-NHZ l.Hg litly-lall-l:riz-13n-V-pnenOXy- m-eLllanol CHZ S(O)z-CHI
z- 2 3 2- z- a m- z y p enoxy-a y CHz-S(O)z-CH3ether O-~uz-lvHz l;ti3 l:rlz-~rll-l:rlz-lvlemyll:l-pnenoxyemyl m-z CHz-S(O)z-CH3ether O-JU2-NriZ 1:H3 l:riz-fall-l:riz-a m-y -p enOXy-a y CHz-S(O)z-CH,ether O-5Uz-NHZ 1:H3 z- z- a m- z y 3-p enoxy-CHz-S(O)z-CH3ethyl ether O-JVZ-NHZ 1.H3 l:riz-loll-1:ri2-lVlelllyll:rig-u-pneriOXy-m-l,l=lVt1)lVriq CHz-S(O)z-CH3ethyl ether O-5V2-NHZ C:H3 l:Hz C;HI-l:riz-lVleitlyl m-t3ri-V-prienOXy CHz-S(O)z-CH3ethyl ether o-~uz-lvtiz 1;H3 z- z- a m- z y enoxye y CHz-S(O)z-CH3ether O-5V2-Nriz C:Hg I:HZ l:Hl-1:H2-lVleUlyl m-l;l=u)lVti2 l:l-pneriOXyelllyl CHz-S(O)z ether O-JUz-lvHz l:rl3 l;rlz-l:rll-l:rlz-lvlemyl m-l,l=u~lvrlz r-pnenoxyewyl CHz-S(O)z-CH3ether o-JVZ tlz 1:H3 l;Hz C;HI-1;H2-lVieTllyl m-l;l=V)lVtlz N 1:ri3-CHz-S(O)z-CH3 phenoxyethyl ether O-JU2-lVHz l;tig l.alz-l;ril-1:ri2-l VleLllyllaig-v-m-l;l=u)lVtlz CHz-S(O)z-CH3 phenoxyethyl ether O-JVy-Ntly Cal3 1:H2-(:ril-1;ri2-l VleLllyl tin-V-m-l:l=V)lVri2 CHz-S(O)z-CH3phenoxyethyl ether o-JUz-lVth laig lalz l:ril-1a12-phenyl m-l.l=lVt1)lVtiz hexane)-O-JUz tiZ 1x13 1:112 l;ril-1:ri2-l:l-pnenyl m-l.l=lVt1)lVri2 lV
hexane)-o-~uz-lvHz l:rl3 l:rlz-l:rll-l;rlz_-p m- z eny hexane)-o-~uz-lvHz l:rl3 l:rlz-l:rll-l:rlz-l:ri3-phenyl m- z hexane)-o-~uz-lvHz lal3 l:rlz l:rll-l;rlz-3_ m- z _p eny hexane)-o-r z r z-v11 U V 11 1 fir' 111111 3 n- -p eny m- z hexane)-o-JVz-Nriz ~ri3 ~riz-aril-~riz-pnenyi m-~l=v)NHz hexane)-O-JUZ Hz 1:H3 l;HZ-l:Hl-l;Hz l:l-pnenyl m-l;l=V)NHz N
hexane)-o-JVZ-NHZ ~ri3 ~riz-aril-~riz-r-pnenyi m-~l=u)NHz hexane)-O-JUz-NHZ 1;H3 l:Hz ;HZ-1;H3-pnenyl m-l;l=U)NHZ
l:Hl-l hexane)-O-JUz-NHZ 1:H3 ~:HZ-liHl-~:HZ-(.;H3-U-prienyl m-Ll=V)NtiZ
hexane)-O-JVz HZ 1:H3 l;Hz-l;Hl-l:Hz tan-u-prieriyl m- z N
hexane)-o-JUz-NHz 1:H3 (:HZ-l;Hl-l:Hz-Arillme p- z hexane)-o-JVz Hz 3 2- Y -am me p- z N
hexane)-O-SUz-NHZ l;Hg l.Hz-C.;HI-1:H2-t'-anllllle p-l;l=NH)lVHz hexane)-O-JV2-NHz 1;H3 l:Hz-l;Hl-1:H2-3-am Ille p- z hexane)-O-JUz-Nriz C.;Hy I;HZ :HZ-3- -am 1ne p-l;Hl-l hexane)-o-5Uz-NHz C:H3 z- 2- n- -am me p- z hexane)-O-5Vz-Nri2 C~H3 l:Hz-l;Hl-C:HZ-m me p- z hexane)-O-JVz Hz C:Hg l;Hz-l:Hl-l:Hy-l;l-anllllle p-N
hexane)-o-~u2 HZ C:H3 l;HZ-l:Hl-~:Hz-r-arillme p- z N
hexane)-O-JUz HZ 1:H3 IIHZ-l;Hl-l:HZ-1:H3-amllrie p- z N
hexane)-O-JUz Hz l:Hj l:Hz-l:Hl-1:H2-1;H3-U-anllme p-N
hexane)-O-JUZ-Nri2 1;H3 l:Hz-l:Hl-l:HZ-II_ -am lrie p-hexane)-O-JUz-NHz 1:H3 l:Hz-l:Hl-l:HZ-eny -amino-car m-OXy 1C
hexane)- acid O-JUZ-Nriz ~H, z- i eny -ammo m- z hexane)- carboxylic acid o-JUz-NHz (:H3 c:Hz-LHl-LHz- r-phenyl-ammo m-~:l=wH)wHz hexane)- carboxylic acid o-JUZ-NHZ 1;H3 C:Hz-C:HI-l:Hz llH3-prieriyl-amlri0m- z hexane)- carboxylic acid o-JUZ-NHZ 1;H3 (:Hz-l:Hl-l;Hz-1:H3-u-prieriyl m- z alrilrio hexane)- carboxylic acid o-5uZ Hz ~:H3 LHZ-LHl-LHZ nn-v-pnenyi ammom-~:l=wri)ivnz N
hexane)- carboxylic acid o-JUz-NHz LH3 ~Hz-~Hl-~Hz- rneny-ammo carnoxyncm-~l=V)mHz hexane)- acid o-~u2 Hz LH3 ~HZ-~Hl-MHz- m-pnenyi-ammo m- z N
hexane)- carboxylic acid o-~uz-NHz ~H, ~HZ-~Hl-~HZ- r-pneny-ammo m-~l=V)mriz hexane)- carboxylic acid o-JUZ-NHZ 1;H3 l:Hz :H2-1:H3-phenyl-ammom-l:l=V)lVHz l;Hl-1 hexane)- carboxylic acid o-JUz Hz 1:H3 C:Hz-l:Hl-~:HZ c:H3 u-pnenyi-ammom-~l=V)wHz N
hexane)- carboxylic acid o-~uz-NHz LH3 uHz-~Hl-uHz- tsn-v-pnenyi-ammom-~l=V)ivHz hexane)- carboxylic acid CHs z- z- a y p ienoxy-aceticm- z J V 1 1Y1 L11 1 1 V~ ivi~t o-t z a z-hexane)- acid ester o-SOz-NHz C:H3 CHz-CH(-CHz- Methyl Cl-phenoxyacehcm-C(=NH)NHz hexane)- acid ester o=SOz-NHz 3 CH2 Hz- Meth~F=phenoxy- m-C(=NH)NHz CH~C acetic hexane)- acid ester O-JUZ-Nriz 1x13 1:ri2-fall-lJriz-itnemyi tai; m-~l=ivn)Nnz pnenoxy-hexane)- acetic acid ester O-~uz-Nriz ~ri3 t:riz-tail-taiz-Metnyi cai3 u-pnenoxy-m-~l=Nti)Ntiz hexane)- acetic acid ester O-JIJZri2 ~-ri3 Lri2-Lril-Lri2-itnemyi tsn-u-pnenoxym-~;l=ivn)ivnz lV
hexane)- acetic acid ester o-SUz-NHz CHj CHz-CH(-CHz- Methyl Yhenoxyacehcm-(:(=U)NHz hexane)- acid ester o-z- z s r z- a y -p enoxyacehcm- z hexane)- acid ester o-SOz-NHz CH3 CHz-CH(-CHz- Methyl r'-phenoxyacehcm-C(=U)NHz hexane)- acid ester O-JVZ-Ntl2 3 ~-tiz-tail-taiz-a Y 3-P enoxy- m- z hexane)- acetic acid ester O-JVZ-Nri2 ~:n, taiz-t:nl-t.nz-a y 3- -p enoxy m- z hexane)- acetic acid ester O-JUy-NHZ s 2- z- a Y n- -p enoxy m- z hexane)- acetic acid ester o~OrNHz CHs CHz-CH(-CHz- Yhenoxyacetic m-C(=NH)NHz acid hexane)-o-z- z CH3 CHz Hz- -p enoxy-acetic m- z CH(-C aci hexane)-o-z- z CH3 CHz-CH(-CHz- -p enoxy- aceticm- z aci hexane)-o-z- z CH3 CHz Hz- 3-p enoxy-aceticm- z CH(-C aci hexane)-o-- z ~ - ~z CH(-CHz- 3- _p enoxy-aceticm- z hexane)- acid o-z- z s z- z- n- -p enoxy aceticm- =NH)NHz aci hexane)-o-2=NHZ CH3 CHz-CH(-CHz- enoxyacehc aci m- z hexane)-o-SOz-NHz CH3 CHz-CH(-CH2 Cl-phenoxyacehc m- z acid hexane)-o-SUz Hz CH3 CHz-CH(-CHz- )~'-phenoxyacehcm-C(=U)NHz N acid hexane)-o-z- Z CH3 CHZ Hz- CH3-phenoxy-aceticm- z CH(-C acid hexane)-o-SOz-NHz CH3 CHz-CH(-CHz- CH3 U-phenoxy m- z acetic hexane)- acid o-SOz-NHz CH3 CHz-CH(-CHz- n- -p enoxy aceticm- z aci hexane)-o-JUz-NHz (:H3 t.;tiz-~atl-Ltlz-enoxye ano m- z hexane)-O-JUZ-NHZ 3 z- z- -p enoxy-a ano m- z hexane)-o-JVz-NHz (:H3 t~tii alz-r-pnenoxy- ethanolm-t:l=ivn)ivnz tail-~
hexane)-o-~u2 Hz cai3 ~ai2 :nz 3-p enoxy-a ano m- z N tail-~
hexane)-o-~Uz-NHz cai3 Ltiz nz- Win,-u-pnenoxy-emanoim- z ~ry-~
hexane)-o-~Uz-Nriz tai3 caiz-t:nl-~nz- rsn-u-pnenoxy m-t.l=ivn)ivnz emanoi hexane)-O-JVZ-Ntl2 1x13 C;tlrl.ril-Lriz-YnenoxyeTnan01 m-l.l=V)tvriz hexane)-o- i- 2 3 z- z- rri=C~2 w.m ua a -p enoxye ano hexane)-O-JVz-NHi C:H3 1;H2-l;H(-l;Hz-r-pnenoxy-emanoim-t,~=U~~riz hexane)-o-SVZ NHz c:Hj ~-Hz-l:H(-l;Hz-3-p enoxy-a ano m- z hexane)-o-~Uz NHz C:H3 l;Hz-(:H(-C:Hz-1:H3 U-prienoxy-m- z etnanot hexane)-o-SUz-NHz c:ri3 l:Hz-(:H(-t,Hz-tin-U-prienoxy- m- z emanoi hexane)-o-SUz-NHz c:H3 c:H2-l:H(-l:Hz-a Y p enoxy-a m-y hexane)- ether o-5Uz-NHz c:H3 l:Hz-c:H(-l;Hz-ivtetnyt la-pnenoxyemyim- z hexane)- ether o-5Vz-Nriz t;H3 t;tt2-c:H(-LHZ-ivtetnyt r-pnenoxy-emytm-hexane)- ether o-5Uz NHZ LH3 c:Hz-l:H(-l:Hzivtetnyt l:rt3-pnenoxy-m-~(=~rt~rrriz hexane)- ethyl ether O-5Uz-NHZ 1;H3 l:rtz-l;H(-1;H2-ivtemyt l:rt3-U-pnenoxy-m-hexane)- ethyl ether o-5Uz-NHZ LH3 l:Hz-l;H(-l:Hz-ivtemyt tsn-u-pnenoxym-~(=lrrt~lrriz hexane)- ethyl ether o-~UZ NHz c:H3 t;Hz-l:H(-latz-ivtemyt rnenoxyetnytm-~;(=U~r~riz hexane)- ether O-5Uz-NHZ c:H3 1:H2-c:H(-I:HZa y -p enoxye m-y hexane)- ether o-~U~ NHz C;H3 c:Hz-(:H(-C:Hz-a y -p enoxye m- z y hexane)- ether o-SUi NHZ C:H3 1;H2-l:H(-(:HZ-a y 3- m- z hexane)- phenoxyethyl ether o-SUZ-NHz C:H3 l;Hz-l:H(-C;HZ-a y 3 - m- z hexane)- phenoxyethyl ether o-5U2-NHz C:H3 l:Hz-l:H(-l:Hz-a y n- m-hexane)- phenoxyethyl ether o-SUz-NHz (_:H3 C:Hz-C:H(-C;Hz-prienyt m- z (HO-phenyl))-o-5Uz-NHz 1:H3 l:Hz-lai(-c.;Hz_-p eny m- z (HO-phenyl))-o-5U2-NHZ C:H3 l:Hz-l:H(-l:Hz-p eriy m-(HO-phenyl))-O-JUz-NHZ C:H3 lain-l:H(-(:Hz~-p eny m-(HO-phenyl))-o-~UZ-Nriz LH3 1:H2-l:H(-l:rtz-l:rt3-U-pnenyt m-(HO-phenyl))-o-~Uz-NHz C;H3 t;Hz-l:H(-l:Hz-tin-u-pnenyt m- z (HO-phenyl))-o-5Uz-NHz C:H3 C:Hz-l:H(-C:Hz-pnenyt m-l:(=U~~ri2 (HO-phenyl))-o-5Uz-NHz t;H3 C:HZ-l:H(-l:Hzla-pnenyl m-l:(=U)mriz (HO-phenyl))-o-5Uz NHz c:H3 t;Hz-l:H(-l;Hz-r-pnenyt m- z (HO-phenyl))-O-5V2-NHZ (:H3 C;HZ-C.;H(-1;H2-3-p eriy m-(HO-phenyl))-O-5U2-NHz C:H3 C:tiz l;H(-1:H2-3- _p eny m-(HO-phenyl))-o-5Uz-Nriz c:H3 2 z- n- -p eny m- z (HO-phenyl))-o-JUZ-NHz 1;H3 z- 2- m me p-(HO-phenyl))-O-JUZ-NHy (:H3 l:riy-l~tl(-1x12_-an11I1e p-(HO-phenyl))-o-- z ~3 z- z_ _~ p- z .... ,_,~~~-,...me (HO-phenyl))-O-JUz-Nriz ~ri3 ~riz-aril-~riz~aij-amime p-~l=Nti~Nttz (HO-phenyl))-o-~uz-Nriz ~ri3 ~riz-aril-~ri2~ri3-u-amime p-~l=NryNriz (HO-phenyl))-o-~uz-Nriz ~ri3 ~riz-~:ril-~riz-nn-u-amime p-~;l=NryNriz (HO-phenyl))-o-~uz-Ntiz ~:ri3 Lr~z-tall-~a~z-Amime p- z (HO-phenyl))-o-z- z s z- z- -am p- z me (HO-phenyl))-o-~uz-Nriz ~ri3 ~riz-aril-~riz-r-amime p-~;l=u)Nrlz (HO-phenyl))-O-JV2-NHZ 1:H3 Z- 2- 3-and p- y me (HO-phenyl))-O-JVZ-Nriz ~;ti, ~riz-aril-t,rlz-~:ri3-v-amime p-~;l=u~Nnz (HO-phenyl))-O-JVZ-NHZ 1;H3 lalz-fall-l;HztSn-V-amlme p-l:l=V)Nriz (HO-phenyl))-O-~uz-NHz ~;H, Lriz-Lril-Lnz-rneny-ammo-carooxync m-t,l=NryNriz (HO-phenyl))-acid o-~uz-NHz ~aij Ltiz-pail-Ltiz~a-rnenyi-ammo m-~l=NryNriz (HO-phenyl))-carboxylic acid O-JUZ-Nriz ~:H3 ~aizway-Lriz-r-pnenyi-ammo m- z (HO-phenyl))-carboxylic acid o-~uz-Ntlz ~;t13 ~tiz-~;til-~tiz-~;ri3-pneny-ammo m-~l=NriJmriz (HO-phenyl))-carboxylic acid o-~u2 tiz ~:H3 tJHZ-tail-LHz-~;t13-u-pnenyi m-Ll=NryNtiz N ammo (HO-phenyl))-carboxylic acid o-JUZ-Nriz ~;H, Lriz-pail-Ltiz-n_ m- z _p eny ammo (HO-phenyl))-carboxylic acid O-JUz-Nriz ~ai3 ~riz-~:ril-~tiz-eny m- z -ammo car oxy is (HO-phenyl))-acid o-~uz-NHz ~ti3 ~riz-aril-~riz-m-pnenyi-ammo m- z (HO-phenyl))-carboxylic acid o-~Uz-Nri2 ~;ti3 ~tiz-~;til-~;ttz_-p m- z eny -ammo (HO-phenyl))-carboxylic acid o-JUZ-Nri2 3 ~.aiz-pail-t,ttz-3-p m- z eny -ammo (HO-phenyl))-carboxylic acid O-JUZ HZ 1:H3 1;H2-lJtil-l;riy-1a13-V-pneriyl-ammo m-N
(HO-phenyl))-carboxylic acid O-JUZ-Ntl2 Lti3 MHz-~;ttl-~;Hz-tsn-u-pnenyi-ammo m-~l=u~Nriz (HO-phenyl))-carboxylic acid o-SOz-NHz CH3 C;Hz-(:H(-CHIa y m- z p enoxy-acetic (HO-phenyl))-acid ester o-SOZ Hz 3 C;Hz (:H(-(:Hz-a y m- z N -p enoxyacehc (HO-phenyl))-acid ester o-SUZ Hz C;H3 C;Hz-C;H(-(:Hz-Methyl m-(:(=NH)NHz N r-phenoxy-acetic (HO-phenyl))-acid ester o-~uz-Ntiz trtij ~:riz-~:ril-~riz-nnemyi m-Ll=1V
~ri3-pnenoxy- ri)1V riz (HO-phenyl))-acetic acid ester O-JUZ-NHZ ~ri3 ~riz-aril-~rizenemy m-~l=NryNriz ~ri3-u-pnenoxy-(HO-phenyl))-acetic acid ester o-~uz-Ntiz ~;ry :riz-~:ril-~riz-enemy m-~:l=NryNriz nn-u-pnenoxy (HO-phenyl))-acetic acid ester o-SOz-NHz CH3 (:Hz-C;H(-(:Hz-Methyl m-C;(=U)NHz Yhenoxyacehc (HO-phenyl))-acid ester o-SUz-NHz LH3 C;Hz-(:H(-(:Hz-Methyl m-(:(=U)NHz (:1-phenoxyacehc (HO-phenyl))-acid ester o-SUz-NHz C;H3 C:Hz-C:H(-C:Hz-a y m-C;(=U)NHz -p enoxyacetlc (HO-phenyl))-acid ester -o- z- z s z- r a Y 3 P epoxy= m-C(=O)NHz (HO-phenyl))-acetic acid ester O-~uz-Nriz Sri, ~riz-aril-~riz-Metnym;ti3-v-pnenoxym-~,l=~)mriz (HO-phenyl))-acetic acid ester O-JVZ-NHy 3 1:ri2-fall-Calz-Mettlyi tSri-V-pnenOXym-l;l=V)lVri2 (HO-phenyl))-acetic acid ester o-SOz-NHz CH3 CHz-CH(-CHz-Yhenoxyacehc m-(:(=NH)NHz acid (HO-phenyl))-o-SOZ NHz CH3 CHz-CH(-CHZCl-phenoxy-aceticm-(:(=NH)NHz acid (HO-phenyl))-o-SOz NHz CH3 CHz-CH(-CHz-r~-phenoxy- aceticm-C(=NH)NHz acid (HO-phenyl))-o-SOZ NHz CH3 CHz-CH(-CHz-3-p epoxy-aceticm- z aci (HO-phenyl))-o-SOz-NHz CH3 CHz-CH(-CHz-3 -p epoxy-aceticm- z (HO-phenyl))-acid o-SOz-NHz CH3 CHz-CH(-CHz-n- -p epoxy aceticm- z aci (HO-phenyl))-o-SOz-NHz CH; Z z- enoxyacehc aci m- z (HO-phenyl))-o- 2 2 3 Z- z- -p enoxyaceric m- z aci (HO-phenyl))-o-~z-NHz CH3 CHz-CH(-CHzr'-phenoxyaceticm-C;(=U)NHz acid (HO-phenyl))-o-Suez-PHz CH3 CHz-CH(-CHZ5-p epoxy-aceticm- z aci (HO-phenyl))-o-~ CH3 CHz-CH(-CHz-3- -p epoxy aceticm- z (HO-phenyl))-acid o- z- z CH3 CHz-CH(-CHz-Bn-U-phenoxy m- z acetic acid (HO-phenyl))-o-JUz NHz lai3 Lrir~-ril-Lrirrnenoxyemanoi m- z (HO-phenyl))-O-JUz NHZ lal; 1:ri2-fail-l;riz-m-pnenoxy-emanoim-~l=ivri)ivriz (HO-phenyl))-o-1u2-NHZ Lti3 Ltiz ~ty-~ry-r-pnenoxy- emanoim-~l=ivri)ivriz (HO-phenyl))-o-5uz NHz t;ti3 ~tiz-~til-Ltiz~ri3-pnenoxy-emanoim-~l=lrri)ivriz (HO-phenyl))-o-~uz Ntiz Lti, ~ry-~ry-~riz-~ri3-~-Pnenoxy-emanoim- z (HO-phenyl))-O-~Uz-Nriz Lti, ~aiz-pail-~aiz-tsn-u-pnenoxy m- z emanoi (HO-phenyl))-O-JU2-NHZ 1:ri3 1;ri2-fall-l:riz-YrieriOXyeman0l m-(HO-phenyl))-O-JU2 NHZ 1;ri3 z- z- -p erioxye ano m-(HO-phenyl))-O-JUZ-Ntiz s 2- r -p epoxy-a ano m- z (HO-phenyl))-o-~u2 NHz cai3 ~aizwailwaiz-3-p epoxy-a ano m- z (HO-phenyl))-o-5uz NHz cai3 ~aizw:ril-~atz-t_ai3-u-pnenoxy-m- z emanoi (HO-phenyl))-O-JV2-NHZ cai, ~;tiz-trtil-~aiz-n_ -p epoxy- m- z a ano (HO-phenyl))-O-~Uz-Nriz ~ri3 ~rizw;ril-~riz-iviemyi pnenoxy-ewyim-~l=ivri)ivriz (HO-phenyl))-ether o-~uZ ivtiz ~ti3 ~rizw:ril-~riz-iviemyi ~i-pnenoxyemyim-~l=ivri)ivriz (HO-phenyl))-ether o-~uz-NHz Ltij caiz-~til-c.aiz-iviemyi r-pnenoxy-einyim-~l=ivri)ivriz (HO-phenyl))-ether o-~uz ivriz Ltij ~aiz-~:ril-~tiz-iviemyi t,ri3 m-l,l=lvtl)LVri2 pnenoxy-(HO-phenyl))-ethyl ether CHs a m-C(=NH)NHz w a~ aa v.m a..ay-w.aay o-z- z z- z- s--phenoxy-ava ua a ~aa v (HO-phenyl))-ethyl ether o-JUz tiz l.ris l:riz-~r1(-c:rtz-Metnyt m- z N tin-V-pnenoxy (HO-phenyl))-ethyl ether o-5uz-Ntiz kris laiz-lay-caiz-Metny m-t;(=l)Nriz rnenoxyemy (HO-phenyl))-ether o-5Vz-Nriz cats caiz-Lti(-caiz-nnemyi m- z la-pnenoxyetnyi (HO-phenyl))-ether o-JUz-NHz 1:ri3 l:riz l;tl(-l:riz-Mettlyl m-l:(=V)lVriz r-pnenOXyelllyl (HO-phenyl))-ether O-JVz-Nriz lai3 l:rlz-t_;tt(-laiz-a m- z Y
(HO-phenyl))- phenoxyethyl ether O-JUz-Nriz 1jt13 t_;tiz-lal(-l:riz- MeiClyll;rij-V-m- z (HO-phenyl))- phenoxyethyl ether O-JVZ-1Vt12 1.r13 l.rlz-lal(-lalz- Memyl tin-V- m-l,~=V)lVrlz (HO-phenyl))-phenoxyethyl ether o-auz-Nriz kris laiz-lai(-laiz-pnenyi m-t;(=rrri)wriz (Cl-phenyl))-O-JVz-Nriz l;tis laiz-~;ti(-l:tiz-la-pneny m-~:~=~ri)Nriz (Cl-phenyl))-o-JVz-Ntiz lass l:riz-~r1(-l:riz--p m- z eny (Cl-phenyl))-O-JUz-Nriz cats la~z-l:rt(-~;t~z-s-p m- z eny (Cl-phenyl))-o-JUz-Nriz 3 z- z- s- m- z -p eny (Cl-phenyl))-O-JVz-Nriz lass t;ti2lai(-laiztsn-u-pnenyi m-~:~=rrri)ivriz (Cl-phenyl))-o-SVz-Nriz cats z- z- p m- z eny (Cl-phenyl))-o-~u2lVtiz lass z- z- -p m- z eny (Cl-phenyl))-o-5u21Vriz Cats z- z- -p m- z eny (Cl-phenyl))-o-JUz-Nriz c:ris l:riz-pry-l:riz-~ri3-pnenyi m-~~=~)mriz (Cl-phenyl))-O-JVz-Ntiz cats laiz-lay-laizl:ryv-pneny m-~.~=v)mriz (Cl-phenyl))-o-JUz tiz lass l:rlz la1(-l:rlz-rsn-u-pnenyi m- z N
(Cl-phenyl))-O-~Vz-NHz 1x13 Calz lal(-l;tlz-Anllme p-~;~=lVt1)iVrlz (Cl-phenyl))-o-JVz-Ntiz Ltis caiz l:ry-l:nz-la-amine p-1:(=~ri)~riz (Cl-phenyl))-O-~VZ t12 lal3 (a12-lal(-laiz-r-amine p-1:~=~ri)rrriz (Cl-phenyl))-o-~uz-lVriz l:ns l:riz-lat(-lJttz-,-am p- z me (Cl-phenyl))-O-JUz-lVriz 1;ri3 1:ri2-l:rl(-l:rlz1;r13-v-arillllle p- z (Cl-phenyl))-O-z z s z- z- n- p-l.~=lVr1)lVrlz -ant me (Cl-phenyl))-o-~uz-lVriz 1x13 lalz-la1(-laiz-Amllne p-1.~=V)lVrlz (Cl-phenyl))-o-~Vz-Nriz a z- z- -am p- z 1rie (Cl-phenyl))-O-JUz-IVHz lalg l;tlz-l;tl(-1:ri2-r-amine p-~:~=~)mriz (Cl-phenyl))-o-JUz-Nriz 1;t13 l:rlz-1:r1(-t;rlz-3-am p- z 1rie (Cl-phenyl))-O-JVz-lVriz 3 2 Y s- p- z -am me (Cl-phenyl))-o- z- z CH3 z- z- n-.... ....~-,_,~~-am me .~
(Cl-phenyl))-O-JVZ-NHZ 1;ri3 1:ri2-fail-1;H2-rneriyl-ammo-CarbOXyllC m-l;l=Ntl)Ntl2 (Cl-phenyl))-acid o-~uz NHZ 3 Lri2-Lril-L'ri2-~a-rnenyi-ammo m- z (Cl-phenyl))-carboxylic acid o-~uz NHZ ~ri3 ~:riz-~;ril-~:riz--p m- z eny -ammo (Cl-phenyl))-carboxylic acid O-JUZ-NHZ Lti3 Ltiz-~;Hl-t;HZ-3-p m- z ieny -ammo (Cl-phenyl))-carboxylic acid o-~uz-NHz Lti3 taiz-pail-~;ttz-cai,-u-pnenyi m- z ammo (Cl-phenyl))-carboxylic acid o-~uz-Ntiz Sri, ~riz-aril-~rizn- m- z -p eny ammo (Cl-phenyl))-carboxylic acid o-~uz-NHz uri, ~riz-~ril-unz-rneny-ammo m-~l=u)wriz carnoxyuc (Cl-phenyl))-acid o-JUZ-Nri2 Sri, ~riz-~ry-~riz-~i-pneny-ammo m- z (CI-phenyl))-carboxylic acid O-JUZ-NHZ ~-ri3 ~riz-~ril-~nz-r-pnenyi-ammo m- z (Cl-phenyl))-carboxylic acid O-JUZ-NY12 Lri3 ~-ri2-~-ril-~-ri2-~-ris-pneny-ammo m-~~=u)mriz (Cl-phenyl))-carboxylic acid o-JVZ-NHZ lal3 1;t12-l;tll-l.:riz-l:rig-V-pneriyl-ammo m-l:l=lJ)Nrl2 (Cl-phenyl))-carboxylic acid O-JUZ-Nri2 uri3 utiz-aril-~riz-nn-u-pnenyi-ammo m-~l=~)wriz (Cl-phenyl))-carboxylic acid o-SOz-NHz CH3 CHz-CH(-CHz-Methyl m-(:(=NH)NHz phenoxy-acetic (Cl-phenyl))-acid ester o-SOz-NHz CH3 CHz-CH(-CHZMethyl m- z Cl-phenoxyacehc (Cl-phenyl))-acid ester o-SOz-NHz CH3 CHz-CH(-CHZa m- z y -p epoxy-acetic (Cl-phenyl))-acid ester O-JVZ-Ntl2 c:H3 r z- a m- z y j-p epoxy-(Cl-phenyl))-acetic acid ester o-~uz-NHz c:H, uriz-aril-uriz-Memyi m-~~=wri)wriz ~ri3-u-pnenoxy-(Cl-phenyl))-acetic acid ester o-JVZ-NH2 C.:H3 1;H2-l:ril-lal2-Memyl m-tSri-V-pneriOXy (Cl-phenyl))-acetic acid ester o-SOz-NHz CH3 CHz-CH(-CHZMethyl m- z Yhenoxyacehc (Cl-phenyl))-acid ester o-SOz-NHz CH3 CHz-CH(-CHz-Methyl m- z Cl-phenoxyacehc (Cl-phenyl))-acid ester o-SOz-NHz CH3 CHz CH(-CHz-Methyl m- z l-phenoxyacehc (Cl-phenyl))-acid ester O-JUZ-Nri2 ~H, ~riz-aril-~riz-Memy m-~l=~)mriz ~rypnenoxy-(Cl-phenyl))-acetic acid ester O-~Vz-NHz ~H3 ~riz-aril-~riz-enemy m- z ~ryu-pnenoxy (Cl-phenyl))-acetic acid ester O-JVz NHz l;rl3 (~H2-l:Hl-1;H2-Meinyl m-l:l=u)Ntl2 tin-u-prienOXy (Cl-phenyl))-acetic acid ester o-SOZ NHz CH3 CHZ CH(-CHz-Yhenoxyacehc m-C(=NH)NHz acid (Cl-phenyl))-o- Oz-NHz CH3 CHZ CH(-CHz-Cl-phenoxy-acetic m-C(=NH)NHz acid (Cl-phenyl))-o-SOz-NHz CH3 CHz-CH(-CHIJ'-phenoxy- m- z acetic acid (Cl-phenyl))-o-SOz-NHz CH3 CHz-CH(-CHzCH3-phenoxy-acetic m- z acid (Cl-phenyl))-o-SOz-NHz CH3 CHz-CH(-CHz-CH3-U-phenoxy-acetic m- z (Cl-phenyl))-acid o-SOz-NHz 3 z- r n- m- z -p epoxy acetic aci (Cl-phenyl))-o-SO ~ CH3 z- z- enoxyacehc m- z aci (Cl-phenyl))-o-JUz-NHz c:H3 C:Hz-(:H(-(:Hz-C:1-phenoxyacehc m-(:(=U)NHz acid (Cl-phenyl))-o-~Uz-NHz C:H3 t:Hz-(:H(-C:Hz-r-phenoxyacehc m-(:(=U)NHz acid (Cl-phenyl))-o-SUz-NHz (:H3 (:Hz-(:H(-C;Hz-C:H3-phenoxy-acehc m-(:(=U)NHz acid (Cl-phenyl))-o-SUz-NHz C:H3 C:Hz-C;H(-(:Hz-C;H3-U-phenoxy m-(:(=U)NHz acehc (Cl-phenyl))-acid o-SUz-NHz 3 z- z- n- m- z -p epoxy acehc aci (Cl-phenyl))-O-JUz-wriz 3 z- z- enoxye m- z ano (Cl-phenyl))-o-~uz-wnz ~-ria ~-nz-~ril-~-riz-~-1-pnenoxy-emanoi m-t:l=mnyvnz (Cl-phenyl))-o-~uz-Ntiz 1:n3 z- z -p m- z epoxy-a ano (Cl-phenyl))-o-~uz-Ntiz t.;n3 ~;nz t:nl-~:nz-~:n3-pnenoxy-emanoi m-t.l=ivnyvnz (Cl-phenyl))-o-~uz-Ntiz t.n3 ~:nz-~:nl-t:nz-3- m- z -p epoxy-a ano (Cl-phenyl))-O-JUz-Nriz ~:ri3 Z z- n- m- z -p epoxy a ano (Cl-phenyl))-O-JVz-Nriz lalg l:riz-fall-lalz-rnenoxyemanoi m-~l=u)~nz (Cl-phenyl))-O-JIJz-Nriz t:n3 ~nz-~nl-t:nz~a-pnenoxyemanoi m- z (Cl-phenyl))-o-Jll2ty :n3 ~:rir~-nl-Lnz-r-pnenoxy-emanoi m-t:l=uyvnz N
(Cl-phenyl))-o-~uz-Ntiz uti3 unz-~nl-unz-un3 m-ul=u~wnz pnenoxy-emanoi (Cl-phenyl))-o-~uz-Nnz t:n3 unz-~nlw:ni~;n3-u-pnenoxy- m- z emanoi (Cl-phenyl))-o-Jl)2tlz Lri3 L'ri2-L'ril-L'ri2-~n-u-pnenoxy- m-t.l=uyvnz N emanoi (Cl-phenyl))-O-~uz-Nriz cai3 ~riz-~nl-~riz-a m- z Y
P
epoxy-a y (Cl-phenyl))-ether o-aVz-Nriz t:ti3 z- z- a m- z y -p enoxye y (Cl-phenyl))-ether o-~u2 Hz s z- z- a m- z N y -p epoxy-a y (Cl-phenyl))-ether o-~Uz-Nriz cai3 taiz-t:nl-t:nz-nnemyi m-t.l=wn~wnz t:n3-pnenoxy-(Cl-phenyl))-ethyl ether o-~u2 Hz t:n3 t:nz-~nl-~nznnecnyi m- z N t:n3-u-pnenoxy-(Cl-phenyl))-ethyl ether o-5uz-Ntiz tai3 t:nz-~nl-t:nza m- z y n--p epoxy (Cl-phenyl))-ethyl ether o-~Uz-Nri2 tai3 t:nz-t:nl-t:nz-nnemyi m- z rnenoxyewyi (Cl-phenyl))-ether o-Jllz-Nri2 tai3 c:nz-trnl-Lnz-Metnym-i-pnenoxyemyi m- z (Cl-phenyl))-ether O-~Uz-Ntiz ~ti, ~nz-~nl-~nz-Memyi m- z r-pnenoxyemyi (Cl-phenyl))-ether O-JUz-Ntiz 1x13 l;tlz-lail-lalz-lVlelllyll.n3- m-l.l=lJ)lVnz (Cl-phenyl))- phenoxyethyl ether O-JUz-Nriz 1:ri3 l:riz-fail-l:riz- MeTriyll:ri3 m-l:l=lJ)lVriz V-(Cl-phenyl))- phenoxyethyl ether o-~uz-Nttz tJtt3 ~;ttz t:nl-t:nz- Memyi tsn-u- m-t.l=a yvnz (Cl-phenyl))-phenoxyethyl ether o-~uz-Nnz lat3 ~;tti tall-tatz-phenyl m-t:l=tvttyvnz ~z)-o-r z s z- z- -P enY m-~:l=Nri)mHz ~2)-o-z- z z- z_ -p eny m-C(=NF~NHz v11 1- 11 1 NHz)_ -o-z- z s z- z_ 3_p eny m2 v11 11 1 ~z) -o-z- z s z- z- m-v11 v 11 1 v 1.11)1.11 s- -P eny NHz)_ 2- 2 m-C(=NH)N
v11 v11 v11 L V 11 1 3 v11~- 2- n- -p eny NHz)_ O-JUz-Nriz 1:H3 l:HZ-l:H(-l:Hz-pnenyl m- z ~z)-O-JUz-NHZ 1:H3 ~HZ-~;Hl-~;HZ m-pnenyi m- z NHz)_ O-~uz-NHz LH, MHz-LH(-MHz- r-pnenyi m- z ~z)_ O-JUZ-Nriz 1:H3 Z z- 3-P enY m- z ~z)-o-z z a z- z- s- -P eny m-C~=0)~z ~z)_ o-JUZ-NHz C;H3 i z- n- -p eny m- z NHz)-o-JUz Hz 3 Z- z m me p- z N
~z)-O-JUZ-NHz 1:H3 1;H2-l:H(-1:H2--an11I1e p-~z)-O-JUz-NHz 1:H3 l:HZ-l:H(-1:H2--ari11I1e p-~z)-O-5U2-NHz 1;H3 l;Hz-(:H(-1:H2-3-am me p-~z)-O-5V2-NHz 1:H3 C;Hz-(:H(-1:H2-3- -aril me p-~z)-O-JUZ Hz 1:H3 l:HZ-l:H(-lalz-t5n-u-anllme p- z N
~2)-o-~Vz-Nriz 1;H3 l;Hz-C:H(-l:Hz-Amllrie p-NHz)_ o-JUz-NHZ 1:H3 l:Hz-C:H(-1:H2-l;l-anllme p- z ~z)-O-aUz-NHZ 1:H3 I:HZ-lai(-1:r12--am me p-~z)-O-JVz Hz (:H3 l:Hz-l:H(-l.HZ-g-am me p- z N
~z)-o-z- z s z- z- 3- -ant me p- z ~2)-O-1Uz-NHZ 1;H3 2- z- n- -am me p- z NHz)-o-JUz Hz 1:H3 r z eny -ammo-car m- z N oxy lc NHz)- acid o-SUz Hz 1:H3 LHz-~;H(-LHZ eny -ammo m- z N
NHz)- carboxylic acid o-JUZ-Nriz ~:H3 ~HZ-~ry-~ty- r-pnenyi-ammo m-~l=mryvnz NHz)- carboxylic acid o-JUZ HZ 1:H3 (:Hz-l:H(-l:Hz-3-p eny -ammo m-N
NHz)- carboxylic acid O-JUZ-NHz 1:H3 l:HZ-l;H(-1:H2-l;Hj U-pnenyl m-l;(=1vH)lvHz ammo NHz)- carboxylic acid o-~uz-NHz ~;H3 LHZ-LH(-~riz nn-u-pnenyi ammom-~:l=mHyvHz NHz)- carboxylic acid O-JVZ Hz 1:H3 l:Hz-l:H(-1;H2-rneny-ammo carnoxyncm-~(=u~NHz N
NHz)- acid o-~uz-NHz ~:H3 MHz-~Hl-~riz-m-pneny-ammo m-~l=m~wriz NHz)- carboxylic acid 0-z- 2 3 2 2- -P eny -ammo m-~~=v~wtiz NHz)- carboxylic acid o-z- x s z- z ~.. .. . ..~ .~,...
3-P enY -~o m- z NHz)- carboxylic acid s r r m-C(=O)NHz U V 11 v11 V 11 1 o-1. z 3- -p eny -ammo z-NHz)- carboxylic acid 0-z- 2 3 2- z- n- -p eny, -ammom-C(=O)NHz NHz)- carboxylic acid o-OZ-NHz CH, CHz-CH(-CHI Methyl phenoxy-aceticm-C(=NH)NHz NHz)- acid ester z-~z 3 z- z- a y -p enoxyacehcm- z J
o-NHz)- acid ester o-r z 3 z- z- a y -p enoXy- m-C(=NH)NHz acetic NHz)- acid ester o-z- z s z- z' a Y s-P epoxy- m- z NHz)- acetic acid ester o-z- z s z- z- m-C(=NH)NHz 1v1 u1 a Yl s- -P epoxy--NHz)- acetic acid ester --o-z- z m - r a Y n- -p epoxy in_C(=NH)NH2 NHz)- acetic acid ester o-SOz-NHz CH3 CHz-CH(-CHz- Methyl Phenoxyacehcm-C(=U)NHz NHz)- acid ester o-2-NHz CH3 CHz-CH(-CHz- Methyl C1-phenoxyacehcm- z NHz)- acid ester o-z- z - CHj CHz-CH(-CHz- Methyl F-phenoxyacehcm- z NHz)- acid ester o-SUz-NHz LH3 ~tiz-l;ti(-caiz-ivietnymrti3-pnenoxy-m- z NHz)- acetic acid ester o-5Vz-NHz c:H3 z- i a Y 3- -P epoxy m- z NHz)- acetic acid ester o-z- 2 3 2- z- m-C(=O)NHz 1v1 ua 11r a y n-O-phenoxy NHz)- acetic acid ester - -o-z- z s z- z- enoxyacehc aci iim-C(=NH)NHz ~z)-o-SOz-NHz CH3 z- r -p epoxy-acetic m- z aci ~z)-o-z ~- CH3 z- z_ -p epoxy- aceticm- z aci ~z)-o-z- z - CH3 CHz-CH(-CHz- 3-p epoxy-aceticm- z aci ~z)-o-z- z j CHz-CH(-CHZ CH3-U-phenoxy-aceticm- z NHz)- acid o-z- z CH3 CHz CHZ Bn-U-phenoxy m- z CH(- acetic acid ~z)--o-z- z 3 z- z- enoxyacehc aci m- _ ~NHz NHz)_ -o-z- z s z- z- -p enoxyacehc m-C(=O)NHz acid NHz)_ o-z-NHz CH3 CHz-CH(-CHz- -p enoxyacehc m- z aci ~z)-o-z-NHz 3 z- z- 3-p epoxy-aceticm- z aci ~z)-o-z-NH2 z- z- 3 -p epoxy aceticm- z J V 1i11 NHz)- acid o-r z s z- z- n- -p epoxy aceticm=C~ O)NHz aci ~z)-o-JVz-Nriz ~;t13 z- r enoxye ano m- z ~z)-O-JUZ-1VHZ lai3 Z- Z- -p epoxy-a ano m-~2)-O-JVZ-lVriz ~ai3 z- z- -p epoxy- a ano m- z ~z)-o- z- z- 3-p m- z ,~ .. ,... enoxy-et ., z s ano z-NHz)_ -o-SOz-NHZ CHI CHz - 3- m- z CH( z- -p enoxy-a ano ~z)-o-~uz-wriz 3 ~riz-~ry-~riznn-u-pnenoxy m-ul=ivti)Ntiz emanoi ~z)-o-~uz-t~ttz 3 ~-riz-~-ril-~-riz-YnenOXyeTnan01 m-l;l=V)Ntl2 ~z)-o-z- z , z- z -p m-~:l=u)~tiz enoxye ano NHz)_ - -o=SO ~ ~3 ~ Z _p m- z ~...~ -...~enoxy-a ano NHz)_ o-z- z 3 z- z- ,-p m-~:l=u)~tiz enoxy-a ano NHz)_ ~ Oz-~z s z- z- 3 m- z -p enoxy-a ano ~z)-o-z- z 3 z- z- n- m- z -p enoxy-a ano ~z)--~ ~ z- a m- z Y
p enoxy-a y NHz)- ether O-JUZ-1Vt12 1.;t13 1.t12-l.tll-l;ti2-enemy m-~:l=mri)r~riz m-pnenoxyemyi NHz)- ether o-~uz-wriz ~ri3 ~riz-aril-~:riz-nnemyi m-ul=Nti)ivtiz r-pnenoxy-emyi NHz)- ether o-au2 riz ~ri3 ~riz-aril-~riz-enemy m-ul=~ri)~riz ~ ~ri3-pnenoxy-NHz)- ethyl ether O-JUZ-wriz ~ri3 ~riz-aril-~riz-enemy m-~:l=~ri)Nriz ~ri3 u-pnenoxy-NHz)- ethyl ether O-JU2 riz ~ri3 ~riz-aril-~riz-Meruyi m-ul=Nri)rVriz w rsn-u-pnenoxy NHz)- ethyl ether O-luz riz ~;ti3 ~aiz-~til-~;riz-iviemyi m-~;l=u)~riz ~ rnenoxyemyi NHz)- ether O-JUz riz 3 ~riz-aril-~tiz enemy m-~l=u)~riz r~ m-pnenoxyerxiy NHz)- ether o-z- z 3 r z a m-Ll=u)Nriz Y
-P
enoxye y NHz)- ether o-r z s z- z- a m- z Y
a-NHz)- phenoxyethyl - ether o-~Oz-1~ CH3 z- CHZ a y 3=O- tn-C~z (-NHz)- phenoxyethyl ether o-z- z a z- z- Memyi rsn-u- m-~l=u)~riz NHz)- phenoxyethyl ether This invention also encompasses all pharmaceutically acceptable isomers, salts, hydrates and solvates of the compounds of formulas I, II and III. In addition, the compounds of formulas I, II and III can exist in various isomeric and tautomeric forms, and all such forms are meant to be included in the invention, along with pharmaceutically acceptable salts, hydrates and solvates of such isomers and tautomers.
The compounds of this invention may be isolated as the free acid or base or converted to salts of various inorganic and organic acids and bases. Such salts are within the scope of this invention. Non-toxic and physiologically compatible salts are particularly useful although other less desirable salts may have use in the processes of isolation and purification.
A number of methods are useful for the preparation of the salts described above and are known to those skilled in the art. For example, the free acid or free base form of a compound of one of the formulas above can be reacted with one or more molar equivalents of the desired acid or base in a solvent or solvent mixture in which the salt is insoluble, or in a solvent like water after which the solvent is removed by evaporation, distillation or freeze drying. Alternatively, the free acid or base form of the product may be passed over an ion exchange resin to form the desired salt or one salt form of the product may be converted to another using the same general process.
Prodrug Derivatives of Compounds This invention also encompasses prodrug derivatives of the compounds contained herein. The term "prodrug" refers to a pharmacologically inactive derivative of a parent drug molecule that requires biotransformation, either spontaneous or enzymatic, within the organism to release the active drug.
Prodrugs are variations or derivatives of the compounds of this invention which have groups cleavable under metabolic conditions. Prodrugs become the compounds of the invention which are pharmaceutically active in vivo, when they undergo solvolysis under physiological conditions or undergo enzymatic degradation. Prodrug compounds of this invention may be called single, double, triple etc., depending on the number of biotransformation steps required to release the active drug within the organism, and indicating the number of functionalities present in a precursor-type form. Prodrug forms often offer advantages of solubility, tissue compatibility, or delayed release in the mammalian organism (see, Bundgard, Design of Prodrugs, pp.
7-9, 21-24, Elsevier, Amsterdam 1985 and Silverman, The Organic Chemistry of Drug Design and Drug Action, pp. 352-401, Academic Press, San Diego, CA, 1992).
Prodrugs commonly known in the art include acid derivatives well known to practitioners of the art, such as, for example, esters prepared by reaction of the parent acids with a suitable alcohol, or amides prepared by reaction of the parent acid compound with an amine, or basic groups reacted to form an acylated base derivative. Moreover, the prodrug derivatives of this invention may be combined with other features herein taught to enhance bioavailability.
As mentioned above, the compounds of this invention find utility as therapeutic agents for disease states in mammals which have disorders of coagulation such as in the treatment or prevention of unstable angina, refractory angina, myocardial infarction, transient' ischemic attacks, thrombotic stroke, embolic stroke, disseminated intravascular coagulation including the treatment of septic shock, deep venous thrombosis in the prevention of pulmonary embolism or the treatment of reocclusion or restenosis of reperfizsed coronary arteries.
Further, these compounds are useful for the treatment or prophylaxis of those diseases which involve the production and/or action of factor Xa/prothrombinase complex. This includes a number of thrombotic and prothrombotic states in which the coagulation cascade is activated which include but are not limited to, deep venous thrombosis, pulmonary embolism, myocardial infarction, stroke, thromboembolic complications of surgery and peripheral arterial occlusion.
Accordingly, a method for preventing or treating a condition in a mammal characterized by undesired thrombosis comprises administering to the mammal a therapeutically effective amount of a compound of this invention. In addition to the disease states noted above, other diseases treatable or preventable by the administration of compounds of this invention include, without limitation, occlusive coronary thrombus formation resulting from either thrombolytic therapy or percutaneous transluminal coronary angioplasty, thrombus formation in the venous vasculature, disseminated intravascular coagulopathy, a condition wherein there is rapid consumption of coagulation factors and systemic coagulation which results in the formation of life-threatening thrombi occurring throughout the microvasculature leading to widespread organ failure, hemorrhagic stroke, renal dialysis, blood oxygenation, and cardiac catheterization.
The compounds of the invention also find utility in a method for inhibiting the coagulation biological samples, which comprises the administration of a compound of the invention.
The compounds of the present invention may also be used in combination with other therapeutic or diagnostic agents. In certain preferred embodiments, the compounds of this invention may be coadministered along with other compounds typically prescribed for these conditions according to generally accepted medical practice such as anticoagulant agents, thrombolytic agents, or other antithrombotics, including platelet aggregation inhibitors, tissue plasminogen activators, urokinase, prourokinase, streptokinase, heparin, aspirin, or warfarin. The compounds of the present invention may act in a synergistic fashion to prevent reocclusion following a successful thrombolytic therapy and/or reduce the time to reperfusion. These compounds may also allow for reduced doses of the thrombolytic agents to be used and therefore minimize potential hemorrhagic side-effects. The compounds of this invention can be utilized in vivo, ordinarily in mammals such as primates, (e.g.
humans), sheep, horses, cattle, pigs, dogs, cats, rats and mice, or in vitro.
The biological properties of the compounds of the present invention can be readily characterized by methods that are well known in the art, for example by the in vitro protease activity assays and in vivo studies to evaluate antithrombotic efficacy, and effects on hemostasis and hematological parameters, such as are illustrated in the examples.
Diagnostic applications of the compounds of this invention will typically utilize formulations in the form of solutions or suspensions. In the management of thrombotic disorders the compounds of this invention may be utilized in compositions such as tablets, capsules or elixirs for oral administration, suppositories, sterile solutions or suspensions or injectable administration, and the like, or incorporated into shaped articles. Subjects in need of treatment (typically mammalian) using the compounds of this invention can be administered dosages that will provide optimal efficacy. The dose and method of administration will vary from subject to subject and be dependent upon such factors as the type of mammal being treated, its sex, weight, diet, concurrent medication, overall clinical condition, the particular compounds employed, the specific use for which these compounds are employed, and other factors which those skilled in the medical arts will recognize.
Formulations of the compounds of this invention are prepared for storage or administration by mixing the compound having a desired degree of purity with physiologically acceptable carriers, excipients, stabilizers etc., and may be provided in sustained release or timed release formulations. Acceptable carriers or diluents for therapeutic use are well known in the pharmaceutical field, and are described, for example, in Remington's Pharmaceutical Sciences, Mack Publishing Co., (A.R.
Gennaro edit. 1985). Such materials are nontoxic to the recipients at the dosages and concentrations employed, and include buffers such as phosphate, citrate, acetate and other organic acid salts, antioxidants such as ascorbic acid, low molecular weight (less than about ten residues) peptides such as polyarginine, proteins, such as serum albumin, gelatin, or immunoglobulins, hydrophilic polymers such as polyvinylpyrrolidinone, amino acids such as glycine, glutamic acid, aspartic acid, or arginine, monosaccharides, disaccharides, and other carbohydrates including cellulose or its derivatives, glucose, mannose or dextrins, chelating agents such as EDTA, sugar alcohols such as mannitol or sorbitol, counterions such as sodium and/or nonionic surfactants such as Tween, Pluronics or polyethyleneglycol.
Dosage formulations of the compounds of this invention to be used for therapeutic administration must be sterile. Sterility is readily accomplished by filtration through sterile membranes such as 0.2 micron membranes, or by other conventional methods. Formulations typically will be stored in lyophilized form or as an aqueous solution. The pH of the preparations of this invention typically will be 3-11, more preferably 5-9 and most preferably 7-8. It will be understood that use of certain of the foregoing excipients, Garners, or stabilizers will result in the formation of cyclic polypeptide salts. While the preferred route of administration is by injection, other methods of administration are also anticipated such as orally, intravenously (bolus and/or infusion), subcutaneously, intramuscularly, colonically, rectally, nasally, transdermally or intraperitoneally, employing a variety of dosage forms such as suppositories, implanted pellets or small cylinders, aerosols, oral dosage formulations and topical formulations such as ointments, drops and dermal patches. The compounds of this invention are desirably incorporated into shaped articles such as implants which may employ inert materials such as biodegradable polymers or synthetic silicones, for example, Silastic, silicone rubber or other polymers commercially available.
The compounds of the invention may also be administered in the form of liposome delivery systems, such as small unilamellar vesicles, large unilamellar vesicles and multilamellar vesicles. Liposomes can be formed from a variety of lipids, such as cholesterol, stearylamine or phosphatidylcholines.
The compounds of this invention may also be delivered by the use of antibodies, antibody fragments, growth factors, hormones, or other targeting moieties, to which the compound molecules are coupled. The compounds of this invention may also be coupled with suitable polymers as targetable drug carriers.
Such polymers can include polyvinylpyrrolidinone, pyran copolymer, polyhydroxy-propyl-methacrylamide-phenol, polyhydroxyethyl-aspartamide-phenol, or polyethyleneoxide-polylysine substituted with palmitoyl residues. Furthermore, compounds of the invention may be coupled to a class of biodegradable polymers useful in achieving controlled release of a drug, for example polylactic acid, polyglycolic acid, copolymers of polylactic and polyglycolic acid, polyepsilon caprolactone, polyhydroxy butyric acid, polyorthoesters, polyacetals, polydihydropyrans, polycyanoacrylates and cross linked or amphipathic block copolymers of hydrogels. Polymers and semipermeable polymer matrices may be formed into shaped articles, such as valves, stems, tubing, prostheses and the like.
Therapeutic compound liquid formulations generally are placed into a container having a sterile access port, for example, an intravenous solution bag or vial having a stopper pierceable by hypodermic injection needle.
Therapeutically effective dosages may be determined by either in vitro or in vivo methods. For each particular compound of the present invention, individual determinations may be made to determine the optimal dosage required. The range of therapeutically effective dosages will be influenced by the route of administration, the therapeutic objectives and the condition of the patient. For injection by hypodermic needle, it may be assumed the dosage is delivered into the body's fluids.
For other routes of administration, the absorption efficiency must be individually determined for each compound by methods well known in pharmacology.
Accordingly, it may be necessary for the therapist to titer the dosage and modify the route of administration as required to obtain the optimal therapeutic effect.
The determination of effective dosage levels, that is, the dosage levels necessary to achieve the desired result, will be readily determined by one skilled in the art.
Typically, applications of compound are commenced at lower dosage levels, with dosage levels being increased until the desired effect is achieved.
The compounds of the invention can be administered orally or parenterally in an effective amount within the dosage range of about 0.,1 to 100 mg/kg, preferably about 0.5 to 50 mg/kg and more preferably about 1 to 20 mg/kg on a regimen in a single or 2 to 4 divided daily doses and/or continuous infusion.
Typically, about 5 to 500 mg of a compound or mixture of compounds of this invention, as the free acid or base form or as a pharmaceutically acceptable salt, is compounded with a physiologically acceptable vehicle, carrier, excipient, binder, preservative, stabilizer, dye, flavor etc., as called for by accepted pharmaceutical practice. The amount of active ingredient in these compositions is such that a suitable dosage in the range indicated is obtained.
Typical adjuvants which may be incorporated into tablets, capsules and the S like are binders such as acacia, corn starch or gelatin, and excipients such as microcrystalline cellulose, disintegrating agents like corn starch or alginic acid, lubricants such as magnesium stearate, sweetening agents such as sucrose or lactose, or flavoring agents. When a dosage form is a capsule, in addition to the above materials it may also contain liquid Garners such as water, saline, or a fatty oil.
Other materials of various types may be used as coatings or as modifiers of the physical form of the dosage unit. Sterile compositions for injection can be formulated according to conventional pharmaceutical practice. For example, dissolution or suspension of the active compound in a vehicle such as an oil or a synthetic fatty vehicle like ethyl oleate, or into a liposome may be desired.
Buffers, preservatives, antioxidants and the like can be incorporated according to accepted pharmaceutical practice.
Preparation of Compounds The compounds of the present invention may be synthesized by either solid or liquid phase methods described and referenced in standard textbooks, or by a combination of both methods. These methods are well known in the art. See, Bodanszky, "The Principles of Peptide Synthesis", Hafner, et al., Eds., Springer-Verlag, Berlin, 1984.
Starting materials used in any of these methods are commercially available from chemical vendors such as Aldrich, Sigma, Nova Biochemicals, Bachem Biosciences, and the like, or may be readily synthesized by known procedures.
Reactions are carried out in standard laboratory glassware and reaction vessels under reaction conditions of standard temperature and pressure, except where otherwise indicated.
During the synthesis of these compounds, the functional groups of the amino acid derivatives used in these methods are protected by blocking groups to prevent cross reaction during the coupling procedure. Examples of suitable blocking groups and their use are described in "The Peptides: Analysis, Synthesis, Biology", Academic Press, Vol. 3 (Gross, et al., Eds., 1981) and Vol. 9 (1987), the disclosures of which are incorporated herein by reference.
Non-limiting exemplary synthesis schemes are outlined directly below, and specific steps are described in the Examples. The reaction products are isolated and purified by conventional methods, typically by solvent extraction into a compatible solvent. The products may be further purified by column chromatography or other appropriate methods.
e1 CFg cHO J
+ ~F3C O,~ O~ KN(Me3Si)2 I ~C02CH3 O O 18-crown-6, THF
CN CN
i v ~ ~ NH2 O
S02NHtBu / ~ N ~ CN
H
AIMe3, DCM
S02NHtBu F
1.HCI, methanol O
2.NH40Ac, methanol, reflux / ~ N ~ I NH2 H NH
O
H2, 10%Pd/C, methanol / \ ~ ( NH2 / N
H NH
/ S02NHB~
\ I \ /
H
I/ \I CN
O
RX, Cs2C03 / SOzNHB~
\ I \ R /
I/ ~ \I
CN
O
1 ) HCI, MeOH
2) NH40Ac, MeOH
R
\ \ /
I / ~ \ I NHZ
O H
O ~ 50% TFA/DCN HO
CN CN
SO zNHtBu SO ZNHtBu / \ - - O I.NHzOH.HCI Et3N
\ / NHZ / \ \ / N \ 2.HOAc, AczO
/ 3.H2, 10% Pd/C
BOP, DIEA, DMF 4.TFA
CN
H O
/ \ \ / N
HN NHp O H N/~N \ / N \ O
HO I ~ ~ N~N~N
BOP, DIEA, DMF
CN CN
O
N ~ \ NON
HN -NHz 1~
a e4 ' O
O
Me0 ~ LiBH4 HO I ~ IBX, DM9D H
THF ~ ~ OMe ~ OMe OMe CN
CN CN
H N NHtBu 2 ~ O=S=O
Me0 (CF3CH20~P(O)CH2C02Me O ~ OMe KN(SiMe3)2, 18~xown-6 CN AIMe3, DCM
1. NCI, MeOH
O ~ OMe 2. NH40Ac, MeOH
S02NHt~ CN
C ~ OMe H2, 10% Pd/C
HN NH2 MeOH
O ~ OMe F O F
LDA, DMF H I ~ (CF3CHZO~P(O)CH2C02Me TI'~F ~ KN(SiMe3)2, 18-crown-6 CN CN
H2N NHtBu F I ~ O=S=O
Me0 ~i ~i O
CN AIMe3, DCM
F
1. HCI, MeOH
O ~ 2. NH40Ac, MeOH
S02NHtBu CN
F
H2, 10% Pd/C
O I i MeOH
S02NHt~
F
'~ O
S02NHt9~
S
Scheme 6 B(OH)2 (CF3S02)20 R~O~ ~ CN
O~ ~O DIEA / DCM CF3S02~0'~ ~O'( Pd(Ph3P)a K3POa / dioxane BuHtN~ ~O
S' _ O' _ H2N ~ / ~ ~ R ~ NH ~
O I ~ O S02NHtBu AIMe3, DCM ~ CN
CN
1. HCI, MeOH
2. NH40Ac, MeOH
NH
NH
H2, 10% Pd/C
MeOH
NH
NH
eme H3C ~ NBS, benzoyl peroxide Br I \ M3N=O H I
I ~ F CCI4 / F CHCI3 ~ F
CN CN CN
H N NHtBu O=S=O
(CF3CH20)2P(O)CHZCOzMe Me0 i I i KN(SiMe3)2, 18-crown-6 O F
CN AIMe3, DCM
\ / \ N I ~ 1. HCI, MeOH
_ _ i O ~F 2. NH40Ac, MeOH
SOZNHtBu CN
/ \ / \ N I ~ H2, 10% Pd/C
O
SOZNHZ F MeOH
HN NHZ
/ \ / \ N I ~
O ~ F
SOZNHz HN NHZ
Compositions and Formulations The compounds of this invention may be isolated as the free acid or base or converted to salts of various inorganic and organic acids and bases. Such salts are within the scope of this invention. Non-toxic and physiologically compatible salts are particularly useful although other less desirable salts may have use in the processes of isolation and purification.
A number of methods are useful for the preparation of the salts described above and are known to those skilled in the art. For example, reaction of the free acid or free base form of a compound of the structures recited above with one or more molar equivalents of the desired acid or base in a solvent or solvent mixture in S which the salt is insoluble, or in a solvent like water after which the solvent is removed by evaporation, distillation or freeze drying. Alternatively, the free acid or base form of the product may be passed over an ion exchange resin to form the desired salt or one salt form of the product may be converted to another using the same general process.
Diagnostic applications of the compounds of this invention will typically utilize formulations such as solution or suspension. In the management of thrombotic disorders the compounds of this invention may be utilized in compositions such as tablets, capsules or elixirs for oral administration, suppositories, sterile solutions or suspensions or injectable administration, and the like, or incorporated into shaped articles. Subjects in need of treatment (typically mammalian) using the compounds of this invention can be administered dosages that will provide optimal efficacy. The dose and method of administration will vary from subject to subject and be dependent upon such factors as the type of mammal being treated, its sex, weight, diet, concurrent medication, overall clinical condition, the particular compounds employed, the specific use for which these compounds are employed, and other factors which those skilled in,the medical arts will recognize.
Formulations of the compounds of this invention are prepared for storage or administration by mixing the compound having a desired degree of purity with physiologically acceptable Garners, excipients, stabilizers etc., and may be provided in sustained release or timed release formulations. Acceptable carriers or diluents for therapeutic use are well known in the pharmaceutical field, and are described, for example, in Remington's Pharmaceutical Sciences, Mack Publishing Co., (A.R.
Gennaro edit. 1985). Such materials are nontoxic to the recipients at the dosages and concentrations employed, and include buffers such as phosphate, citrate, acetate and other organic acid salts, antioxidants such as ascorbic acid, low molecular weight (less than about ten residues) peptides such as polyarginine, proteins, such as serum albumin, gelatin, or immunoglobulins, hydrophilic polymers such as polyvinalpyrrolidinone, amino acids such as glycine, glutamic acid, aspartic acid, or arginine, monosaccharides, disaccharides, and other carbohydrates including cellulose or its derivatives, glucose, mannose or dextrins, chelating agents such as EDTA, sugar alcohols such as mannitol or sorbitol, counterions such as sodium and/or nonionic surfactants such as Tween, Pluronics or polyethyleneglycol.
Dosage formulations of the compounds of this invention to be used for therapeutic administration must be sterile. Sterility is readily accomplished by filtration through sterile membranes such as 0.2 micron membranes, or by other conventional methods. Formulations typically will be stored in lyophilized form or as an aqueous solution. The pH of the preparations of this invention typically will be between 3 and 11, more preferably from 5 to 9 and most preferably from 7 to 8.
It will be understood that use of certain of the foregoing excipients, carriers, or stabilizers will result in the formation of cyclic polypeptide salts. While the preferred route of administration is by injection, other methods of administration are also anticipated such as intravenously (bolus and/or infusion), subcutaneously, intramuscularly, colonically, rectally, nasally or intraperitoneally, employing a variety of dosage forms such as suppositories, implanted pellets or small cylinders, aerosols, oral dosage formulations and topical formulations such as ointments, drops and dermal patches. The compounds of this invention are desirably incorporated into shaped articles such as implants which may employ inert materials such as biodegradable polymers or synthetic silicones, for example, Silastic, silicone rubber or other polymers commercially available.
° The compounds of this invention may also be administered in the form of liposome delivery systems, such as small unilamellar vesicles, large unilamellar vesicles and multilamellar vesicles. Liposomes can be formed from a variety of lipids, such as cholesterol, stearylamine or phosphatidylcholines.
The compounds of this invention may also be delivered by the use of antibodies, antibody fragments, growth factors, hormones, or other targeting moieties, to which the compound molecules are coupled. The compounds of this invention may also be coupled with suitable polymers as targetable drug Garners.
Such polymers can include polyvinylpyrrolidone, pyran copolymer, polyhydroxy-propyl-methacrylamide-phenol, polyhydroxyethyl-aspartamide-phenol, or polyethyleneoxide-polylysine substituted with palmitoyl residues. Furthermore, the factor Xa inhibitors of this invention may be coupled to a class of biodegradable polymers useful in achieving controlled release of a drug, for example polylactic acid, polyglycolic acid, copolymers of polylactic and polyglycolic acid, polyepsilon caprolactone, polyhydroxy butyric acid, polyorthoesters, polyacetals, polydihydropyrans, polycyanoacrylates and cross linked or amphipathic block copolymers of hydrogels. Polymers and semipermeable polymer matrices may be formed into shaped articles, such as valves, stems, tubing, prostheses and the like.
Therapeutic compound liquid formulations generally are placed into a container having a sterile access port, for example, an intravenous solution bag or vial having a stopper pierceable by hypodermic injection needle.
Therapeutically effective dosages may be determined by either in vitro or in vivo methods. For each particular compound of the present invention, individual determinations may be made to determine the optimal dosage required. The range of therapeutically effective dosages will naturally be influenced by the route of administration, the therapeutic objectives, and the condition of the patient.
For injection by hypodermic needle, it may be assumed the dosage is delivered into the body's fluids. For other routes of administration, the absorption efficiency must be individually determined for each inhibitor by methods well known in pharmacology.
Accordingly, it may be necessary for the therapist to titer the dosage and modify the route of administration as required to obtain the optimal therapeutic effect.
The determination of effective dosage levels, that is, the dosage levels necessary to achieve the desired result, will be within the ambit of one skilled in the art.
Typically, applications of compound are commenced at lower dosage levels, with dosage levels being increased until the desired effect is achieved.
A typical dosage might range from about 0.001 mg/kg to about 1000 mg/kg, preferably from about 0.01 mg/kg to about 100 mg/kg, and more preferably from about 0.10 mg/kg to about 20 mg/kg. Advantageously, the compounds of this invention may be administered several times daily, and other dosage regimens may also be useful.
Typically, about 0.5 to 500 mg of a compound or mixture of compounds of this invention, as the free acid or base form or as a pharmaceutically acceptable salt, is compounded with a physiologically acceptable vehicle, carrier, excipient, binder, preservative, stabilizer, dye, flavor etc., as called for by accepted pharmaceutical practice. The amount of active ingredient in these compositions is such that a suitable dosage in the range indicated is obtained.
Typical adjuvants which may be incorporated into tablets, capsules and the like are a binder such as acacia, corn starch or gelatin, and excipient such as microcrystalline cellulose, a disintegrating agent like corn starch or alginic acid, a lubricant such as magnesium stearate, a sweetening agent such as sucrose or lactose, or a flavoring agent. When a dosage form is a capsule, in addition to the above materials it may also contain a liquid Garner such as water, saline, a fatty oil. Other materials of various types may be used as coatings or as modifiers of the physical form of the dosage unit. Sterile compositions for injection can be formulated according to conventional pharmaceutical practice. For example, dissolution or suspension of the active compound in a vehicle such as an oil or a synthetic fatty vehicle like ethyl oleate, or into a liposome may be desired. Buffers, preservatives, antioxidants and the like can be incorporated according to accepted pharmaceutical practice.
In practicing the methods of this invention, the compounds of this invention may be used alone or in combination, or in combination with other therapeutic or diagnostic agents. 1n certain preferred embodiments, the compounds of this inventions may be coadministered along with other compounds typically prescribed for these conditions according to generally accepted medical practice, such as anticoagulant agents, thrombolytic agents, or other antithrombotics, including platelet aggregation inhibitors, tissue plasminogen activators, urokinase, prourokinase, streptokinase, heparin, aspirin, or warfarin. The compounds of this invention can be utilized in vivo, ordinarily in mammals such as primates, such as humans, sheep, horses, cattle, pigs, dogs, cats, rats and mice, or in vitro.
The preferred compounds of the present invention are characterized by their ability to inhibit thrombus formation with acceptable effects on classical measures of coagulation parameters, platelets and platelet function, and acceptable levels of bleeding complications associated with their use. Conditions characterized by undesired thrombosis would include those involving the arterial and venous vasculature.
With respect to the coronary arterial vasculature, abnormal thrombus formation characterizes the rupture of an established atherosclerotic plaque which is S the major cause of acute myocardial infarction and unstable angina, as well as also characterizing the occlusive coronary thrombus formation resulting from either thrombolytic therapy or percutaneous transluminal coronary angioplasty (PTCA).
With respect to the venous vasculature, abnormal thrombus formation characterizes the condition observed in patients undergoing major surgery in the lower extremities or the abdominal area who often suffer from thrombus formation in the venous vasculature resulting in reduced blood flow to the affected extremity and a predisposition to pulmonary embolism. Abnormal thrombus formation further characterizes disseminated intravascular coagulopathy commonly occurs within both vascular systems during septic shock, certain viral infections and cancer, a condition wherein there is rapid consumption of coagulation factors and systemic coagulation which results in the formation of life-threatening thrombi occurring throughout the microvasculature leading to widespread organ failure.
The compounds of this present invention, selected and used as disclosed herein, are believed to be useful for preventing or treating a condition characterized by undesired thrombosis, such as (a) the treatment or prevention of any thrombotically mediated acute coronary syndrome including myocardial infarction, unstable angina, refractory angina, occlusive coronary thrombus occurring post-thrombolytic therapy or post-coronary angioplasty, (b) the treatment or prevention of any thrombotically mediated cerebrovascular syndrome including embolic stroke, thrombotic stroke or transient ischemic attacks, (c) the treatment or prevention of any thrombotic syndrome occurring in the venous system including deep venous thrombosis or pulmonary embolus occurnng either spontaneously or in the setting of malignancy, surgery or trauma, (d) the treatment or prevention of any coagulopathy including disseminated intravascular coagulation (including the setting of septic S shock or other infection, surgery, pregnancy, trauma or malignancy and whether associated with multi-organ failure or not), thrombotic thrombocytopenic purpura, thromboangiitis obliterans, or thrombotic disease associated with heparin induced thrombocytopenia, (e) the treatment or prevention of thrombotic complications associated with extracorporeal circulation (e.g. renal dialysis, cardiopulmonary bypass or other oxygenation procedure, plasmapheresis), (f) the treatment or prevention of thrombotic complications associated with instrumentation (e.g.
cardiac or other intravascular catheterization, infra-aortic balloon pump, coronary stmt or cardiac valve), and (g) those involved with the fitting of prosthetic devices.
Anticoagulant therapy is also useful to prevent coagulation of stored whole blood and to prevent coagulation in other biological samples for testing or storage.
Thus the compounds of this invention can be added to or contacted with any medium containing or suspected to contain factor Xa and in which it is desired that blood coagulation be inhibited, e.g., when contacting the mammal's blood with material such as vascular grafts, stems, orthopedic prostheses, cardiac stems, valves and prostheses, extra corporeal circulation systems and the like.
Without further description, it is believed that one of ordinary skill in the art can, using the preceding description and the following illustrative examples, make and utilize the compounds of the present invention and practice the claimed methods. The following working examples therefore, specifically point out preferred embodiments of the present invention, and are not to be construed as limiting in any way the remainder of the disclosure.
EXAMPLES
H H
OMe I I
i O
CN
To a solution of bis(2,2,2-trifluoroethyl)(methoxylcarbonylmethyl)phosphate (0.665m1, 3.14mmo1) and 18-crown-6 (4.14g, 15.7mmo1) in tetrahydrofuran (SOmI) at -78 °C was added potassium bis(trimethylsilyl)amide (6.3m1, 3.15mmo1) dropwise. After the addition was complete, 3-cyanobenzaldehyde (0.412g, 3.14mmo1) in tetrahydrofuran (lOml) was added at -78 °C. The mixture was stirred at -78 °C for additional 1 hr. Saturated ammonia chloride solution was added to quench the reaction. Ether and water were added. The organic layer was separated, and the aqueous layer was extracted with ether once more. The combined organic extracts were dried over magnesium sulfate and concentrated in vacuo. The crude residue was purified by silica gel column chromatography using solvent system 10% ethyl acetate in hexane as eluent to give the title compound as a white solid (1.12g, 100%).
ES-MS (M+H)+ = 188.
xam 1e 2 / \
SOzNHtBu To a solution of tert-butylamine (5.73g, 78.4mmo1) and triethylamine (16.6m1, 1 l9mmol) in dichloromethane (200m1) in an ice bath was added benzenesulfonyl chloride (13.85g, 78.4mmo1) dropwise. The mixture was stirred at room temperature overnight. It was washed with saturated sodium carbonate (60m1) and brine (60m1). The organic layer was separated, and the aqueous layer was extracted with dichloromethane (2x50m1). The combined organic extracts were dried over magnesium sulfate. The solvent was evaporated in. vacuo to give the title compound as a light yellowish solid (15.92g, 95%). ES-MS (M+H)+ = 214.
Example 3 B~oHy~
S02NHtBu To a solution of the compound of example 2 (15.92g, 74.7mmo1) in tetrahydrofuran (200m1) in an ice bath was added 1.6M n-butyllithium in hexane (100m1, 164mmol) dropwise over 30 minutes. The mixture remained a clear solution. In an ice bath it was added triisopropylborate (24.1m1, 104mmo1) dropwise. The mixture was stirred at room temperature for 3.Shrs, solution becoming cloudy. After it was cooled in an ice bath, 1N hydrochloride (200m1) was added. The mixture was stirred at room temperature overnight. It was extracted with ether (2x50m1). The organic extract was washed with 1N sodium hydroxide (2x60m1). The aqueous solution was acidified to pH=1 with 6N hydrochloride, and then extracted with ether (2x100m1).
The ether extract was dried over magnesium sulfate, and concentrated in vacuo to give the title compound as a while solid (ll.Sg, 60%). ES-MS (M+H)+ = 258.
Ex 4 S02NHtBu F
To a solution of the compound of example 3 (2.06g, 8mmo1) in toluene (60m1) was added water (4m1), 8N sodium hydroxide (8m1), isopropanol (16m1), 2-fluoro-4-iodoaniline (3.8g, l6mmol) and tetrakis(triphenylphosphine)palladium(0) (464mg, 0.4mmo1). The mixture was refluxed for 3-4 hrs, cooled to room temperature, and diluted with ethyl acetate. The organic layer was washed with water (25m1), and dried over magnesium sulfate. After the evaporation of the solvent in vacuo, the crude reside was purified by silica gel column chromatography using solvent system 20-30% ethyl acetate in hexane as eluent to give the title compound as a white solid (1.49g, 58%). ES-MS (M+H)+=323.
Ex a ~I
CN
S02NHtBu F
S To a solution of compound of example 4 (161mg, O.Smmol) in dichloromethane (5m1) was added 2.0M trimethylaluminum in hexane (0.75m1, l.Smmo1). The mixture was stirred at room temperature for 30 minutes, methane gas evolved. A
solution of the compound of example 1 (94mg, O.Smmol) in dichloromethane (1m1) was added. The mixture was stirred at room temperature overnight. 1N
hydrochloride was added to acidify the solution to pH=2. After the addition of water and dichloromethane, the organic layer was separated, and the aqueous layer was extracted with dichloromethane. The combined organic extracts were dried over magnesium sulfate, and concentrated in vacuo to give the title compound as a yellow oil (260mg, 100%). ES-MS (M+H)+ = 478.
Example 6 / ~ ~ I NHz N
H NH
To a solution of the compound of example 5 (100mg, 0.21mmo1) in absolute methanol (3m1) in an ice bath was saturated with hydrochloride gas for 10 minutes.
The mixture was stirred at room temperature for 3 hrs. After the evaporation of solvent in vacuo, the residue was dissolved in absolute methanol (3m1), and ammonia acetate (97mg, 1.26mmo1) was added. The mixture was refluxed for 3 hrs.
The solvent was evaporated in vacuo. The crude residue was purified by RP-HPLC
to give the title compound as a white powder (53mg, 58%). ES-MS (M+H)+ = 439.
Example 7 N ~ I NH2 H NH
To a solution of the compound of example 6 (30mg, 0.07mmo1) in absolute methanol (2m1) was added 10% Pd/C (catalytic amount). The mixture was hydrogenated under balloon for lhr. After the filtration through Celite, the solvent was evaporated in vacuo. The residue was purified by RP-HPLC to give the compound as a white powder (25mg, 81 %). ES-MS (M+H)+ = 441.
Example 8 S02NHtBu CI
1 S To a solution of the compound of example 3 (2.06g, 8mmol) in toluene (60m1) was added water (4m1), 8N sodium hydroxide (8m1), isopropanol (16m1), 2-chloro-4-iodoaniline (4.06g, l6mmol) and tetrakis(triphenylphosphine)palladium(0) (464mg, 0.4mmo1). The mixture was refluxed for 3-4 hrs, cooled to room temperature, and diluted with ethyl acetate. The organic layer was washed with water (25m1), and dried over magnesium sulfate. After the evaporation of the solvent in vacuo, the crude reside was purified by silica gel column chromatography using solvent system 20-30% ethyl acetate in hexane as eluent to give the title compound as a white solid (1.43g, 53%). ES-MS (M+H)+= 339.
am 1 ~I
~ ~ / H ~ CN
S02NHtBu CI
To a solution of the compound of example 8 (100mg, 0.3mmo1) in dichloromethane (5m1) was added 2.0M trimethylaluminum in hexane (0.45m1, 0.9mmo1). The mixture was stirred at room temperature for 30 minutes, methane gas evolved. A
solution of the compound of example 1 (SSmg, 0.3mmo1) in dichlodomethane (1m1) was added. The mixture was stirred at room temperature overnight. 1N
hydrochloride was added to acidify the solution to pH=2. After the addition of water and dichloromethane, the organic layer was separated, and the aqueous layer was extracted with dichloromethane. The combined organic extracts were dried over magnesium sulfate, and concentrated in vacuo to give the title compound as a greenish solid (1 l Omg, 70%). ES-MS (M+H)+ = 494.
Example 10 ~ ~ I NH2 N
H NH
To a solution of the compound of example 9 (100mg, 0.2mmol) in absolute methanol (3m1) in an ice bath was saturated with hydrochloride gas for 10 minutes.
The mixture was stirred at room temperature for 3 hrs. After the evaporation of the solvent in vacuo, the residue was dissolved in absolute methanol (3m1), and ammonia acetate (92mg, l.2mmo1) was added. The mixture was refluxed for 3 hrs.
The solvent was evaporated in vacuo. The crude residue was purified by RP-HPLC
to give the title compound as a white powder (46mg, 51 %).
ES-MS (M+H)+ = 456.
Example 11 Production of 3-[(2-2-furyl)-5-oxo-1,3-oxazolin-4-ylidene)methyl]
benzenecarbonitrile.
N ~I
~O
//O
CN
A mixture of 3-cyanobenzaldehyde (2.102g, 15.320mmo1), N-2-furoylglycine (1.846g, 10.914mmo1), and sodium acetate (0.636g, 7.753mmo1) in 15m1 acetic anhydride was refluxed for 7 hours. The mixture was then cooled to room temperature before cooling in the freezer over night. The solid was washed with ice cold water then filtered (0.472g, 1.788mmo1, 16%). ES-MS(M+H)+=265.
F~xa_mple 1 Production of (2E)-N-[4(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)-2-(2-furylcarbonylamino)prop-2-enamide To a solution of {[2-(4-aminophenyl)phenyl]sulfonyl}(tert-butyl)amine (0.152g, O.SOOmmol) in 9m1 DCM was added trimethylaluminum (1m1, 2M solution in hexanes, 2mmo1) which was allowed to stir for'/2 hour. Then 3-[(2-(2-furyl)-5-oxo-1,3-oxazolin-4-ylidene)methyl]benzenecarbonitrile (0.11g, 0.417mmo1) was added drop wise as a solution in 3m1 DCM. Three hours later 6M HCl was added drop wise to pH=0. l Oml portions of water and DCM were also added and the aqueous layer was extracted twice with l Oml portions of DCM. The organic layers were dried over MgS04, filtered and concentrated in vaccu to yield the desired product (0.259, 0.456, 109%). ES-MS(M+H)+=569.
Example 13 Production of 3-(2-{N-[4-(2-{[(tert-butyl) amino] sulfonyl } phenyl)phenyl] carbamoyl } -2-(2-furylcarbonylamino)ethyl)benzenecarboxamidine To a solution of (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)-2-(2-furylcarbonylamino)prop-2-enamide (0.259g, 0.456mmo1) in 7m1 ethanol was added hydroxyamine (0.192g, 2.763mmo1) and triethyl amine (0.762m1, 5.407mmo1). This mixture was refluxed for 2 hours before it was concentrated in vaccu. The residue was dissolved in AcOH (5m1), then acetic anhydride (0.30m1, 3.182mmo1) was added and the mixture was allowed to stir forl.5 hours. The mixture was concentrated in vaccu. The residue was dissolved in dry MeOH
(3m1), 5%Pd/C (22.7m8) was added. A balloon filled with hydrogen gas was fitted to the flask with an adapter. The flask was evacuated and backfilled with hydrogen gas three times before being run for 0.75 hour. The mixture was then filtered over a bed of celite and concentrated in vaccu. The residue was purified via Preparative HPLC
to yield the desired product (0.0758, 0.128mmo1, 28%). ES-MS(M+H)+=588.
Example 14 Production of 3-(2-(2-furylcarbonylamino)-2-{N-[4-(2-sulfamoylphenyl)phenyl]-carbamoyl } ethyl)benzenecarboxamidine 3-(2- {N-[4-(2- { [(tert-butyl)amino] sulfonyl } phenyl)phenyl] carbamoyl } -2-(2-fiuyl-carbonylamino)ethyl)benzenecarboxamidine (0.0758, 0.128mmo1) was dissolved with TFA (6m1) for 2hours. The mixture was concentrated in vaccu and the residue was purified via Preparative HPLC, (0.0408, 0.075mmo1, 58%). ES-MS(M+H)+=532.
Exam 1p a 15 Production of (tert-butyl)(phenylsulfonyl)amine o~
S~o / \
To a solution of benzenesulfonyl chloride (30.008, 169.86mmol) in 100m1 DCM, in an ice bath, was added butyl amine (18m1, 171.28mmo1), then triethylamine(35m1, 251.1 lmmol), drop wise via addition funnel. This was allowed to warm to room temperature over 3hr. The mixture was then filtered and the filtrate was concentrated in vaccu. The pale yellow solid (35.03g, 164.46mmo1, 97%) was then rinsed with minimal amounts of DCM. ES-MS (M+Na)+=236.
S
Example 16 Production of (tert-butyl)(phenylsulfonyl)amine H
p B-OH
,_ To (tent-butyl)(phenylsulfonyl)amine (17.43g, 81.83mmo1) in 180m1 dry THF in an ice bath was added nBuLi (66m1, 2.5M in hexanes) via addition funnel. Then triisopropyl borate (33m1, 143.06mmo1) was added via addition funnel. The mixture was warmed to room temperature and allowed to stir for 4hr. The reaction mixture was then cooled in an ice bath before HCL (82m1, 3M) was added drop wise. This was allowed to stir at room temperature for 3hr. The mixture was then put in the freezer over the weekend. The reaction was then warmed to room temperature and extracted with ether. The aqueous layers were washed twice more with ether.
The combined organic layers were washed three times with SM NaOH aqueous solution.
The combined basic layers were acidified to pH=1 with 6M HCL solution. These acidified layers were then extracted three times with ether. These ether layers were then dried over MgS04, f ltered, then concentrated in vaccu to about SOmI
solution.
To this solution was added hexanes and a minimal amount of ethyl acetate. A
white precipitate is observed and the mixture in stored in the freezer to allow for crystallization. The white solid is then filtered and collected (14.65g, 57mm1, 70%) ES-MS (M+H)+=25 8.
Production of {[2-(4-aminophenyl)phenyl]sulfonyl}(tert-butyl)amine HyN
NH
~O
To a solution of 2-[(tert-butyl amino)sulfonyl] phenyl boronic acid (6.00g, 23.35mmo1) in 120m1 toluene was added water (16m1), isopropanol (60m1), and NaOH (40m1, SM aqueous solution). To this were added 4-bromoaniline and Pd(Ph3P)4. This heterogeneous mixture is then refluxed for 6hr, then stirred at room temperature over night before refluxing for another l.Shr. The reaction mixture is then extracted with water and ethyl acetate. The aqueous layer is extracted twice with ethyl acetate. The organic layers are then dried over MgS04, filtered and concentrated in vaccu. The crude residue is purified by silica gel flash chromatography. The desired product can be eluded with 30% ethyl acetate in hexanes and concentrated to an orange solid (5.06g, 16.65, 71 %). ES-MS(M+H)+=305.
Example 18 O
H ~NH2 Step (a):
To a 0°C solution of 4-((2-N-t-butylamonisulfonyl)phenyl) aniline (74.1 mg, 0.3 mmol, 1.0 equiv) in 5 mL of CHZC12 was added a solution of AlMe3 (2M in hexanes, 0.7 mL, 5 equiv). After l5min, methyl 2-(3-cyanophenyl)acrylate (56.1 mg, 1.0 equiv) was added. The resulting solution was stirred overnight, carefully quenched with water, diluted with ethyl acetate. The organic layer was dried, evaporated and chromatographied on silica gel to give the product in 55% yield. LRMS found for C23H19N2~3'~ (M+H)+: 403.1.
Step (b):
The compound obtained in step (a) (25 mg) was dissolved in S mL of methanol .
The reaction mixture was cooled to 0°C and HCl gas was bubbled in until saturation. The mixture was stirred at rt overnight. The solvent was evaporated and the resulting residue was treated with ammonium acetate and 10 ml methanol at reflux temperature for 2 h. The solvent was removed at reduced pressure and the crude benzamidine was purified by HPLC (C18 reversed phase) eluting with 0.5% TFA in H20/CH3CN to give the desired salt in 77% yield. LRMS found for CZgH22N3~3'S
(M+H)+: 420.1.
Step (c):
The compound obtained in step (b) (8 mg) and S mg of 10% Pd/C was suspended in 1 mL of methanol . The reaction mixture was stirred under 1 atm hydrogen balloon for 2h and filtered. The solvent was removed at reduced pressure and the crude benzamidine was purified by HPLC (C18 reversed phase) eluting with 0.5% TFA in H20/CH3CN to give the desired salt in 63% yield. LRMS found for C23H24N3~3S
(M+H)+: 422.1.
Example 19 F
CN
2-Fluoro-5-methyl benzonitrile (1.26g, 9.32 mmol) was mixed with NBS (1.66 g, 9.32 mmol), benzoyl peroxide (79 mg, 0.33 mmol) in CC14 (45mL). The mixture was refluxed for 2.5 hrs. It was cooled to room temperature, filtered and concentrated in vacuo to give the title compound. ES-MS (M+H)+ = 213.1.
Example 20 O
F
CN
To a solution of compound of example 19 (9.32 mmol) in CHC13 (50 mL), was added trimethylamino N-oxide (1.7 g, 23.3 mmol). The mixture was refluxed for hrs. Water was added. The organic layer was dried over MgS04, filtered and filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography using solvent system 20% EtOAc in hexane as eluant to give the title compound. ES-MS (M+H)+ = 150.1.
Exam In a 21 Me0 O
F
CN
To a solution of bis(2,2,2-trifluoroethyl)(methoxycarbonylmethyl) phosphonate (0.12 mL, 0.58 mmol) and 18-crown-6 (770 mg, 2.92 mmol) in THF (5 mL) at -78°C, was added potassium bis(trimethylsilyl)amide (1.17 mL, 0.57 mmol) dropwise. After the addition was complete, compound of example 2 (87 mg, 0.58 mmol) in THF (2 mL) was added. The mixture was stirred at -78°C for 1 hour.
Aqueous NH4Cl solution was added to quench the reaction. Water and EtOAc was added to the mixture. The organic layer was dried over MgS04, filtered and concentrated in vacuo. This was purified by silica gel column chromatography using solvent system 20% EtOAc in hexane as eluant to give the title compound (85 mg, 71 %). ES-MS (M+H)+ = 206.1.
exam In a 22 S02NHtBu H2N \ / \ /
To a solution of compound of example 3 (6.4 g, 25 mmol) in toluene (120 mL) was added water (15 mL), SN NaOH solution (38.5 mL), isopropanol (60 mL) 4-bromoaniline and tetrakis(triphenylphosphine)palladium(0). The mixture was refluxed for six hours, cooled to room temperature, diluted with EtOAc. The organic layer was washed with water, dried with MgS04, filtered and concentrated.
This was purified by silica gel column chromatography using solvent system 30%
EtOAc in hexane as eluant to give the title compound (5g, 66%). ES-MS (M+H)+ _ 305.1.
Example 23 / \ / \ N
O ~ F
S02NHtBu CN
To a solution of compound of example 22 (121.6 mg, 0.4 mmol) in DCM (3 mL) was added trimethylaluminum (0.6 mL, 2M in hexane) dropwise. The reaction mixture was stirred at room temperature for 30 min. Compound of example 21 (82 mg, 0.4 mmol) in DCM (2 mL) was added dropwise. The mixture was stirred at room temperature overnight. 2N HCl was added to pH 2. Water and DCM were added. The organic layer was dried over MgS04 and concentrated in vacuo. It was purified by silica gel column chromatography using solvent system 50% EtOAc in hexane as eluant to give the title compound. ES-MS (M+Na)+ = 500.1.
Example 24 / \ / \
O / F
A solution of the compound of example 23 (99 mg, 0.208 mmol) in MeOH (10 mL) was treated with a stream of HCl gas for 10 min. at 0°C. The resulting solution was capped, stirred at room temperature overnight and evaporated in vacuo. The residue was reconstituted in MeOH (10 mL) and the mixture was treated with NH40Ac (80 mg, 1.04 mmol). The reaction mixture was refluxed for 2 hrs. and concentrated in vacuo. The obtained residue was purified by RP-HPLC to give the title compound as a white powder. ES-MS (M+H)+ = 439.1.
Exam In a 25 / \ / \
O / F
The compound of example 24 (10 mg, 0.022 mmol) was dissolved in MeOH (5 mL) and 10% Pd/C (catalytic amount) was added. The mixture was hydrogenated under balloon overnight, filtered through Celite to remove the catalyst and the filtrate was evaporated. The obtained residue was purified by RP-HPLC to give the title compound as a white powder. ES-MS (M+H)+ = 441.1.
Exam In a 26 O F
H
CN
To a solution of LDA (2.6 mL, 2N solution in hexane, 5.2 mmol) in THF (10 mL) at -78°C, was added 4-fluorobenzonitrile in THF (10 mL) dropwise. The mixture was stirred at -78°C for 1 hour. To this was added DMF (0.4 mL, 0.55 mmol).
The mixture was stirred at -78°C for another 15 min., quenched rapidly with AcOH (2 mL) and water (10 mL), extracted with ether (SO mL). The ether extracts were washed with 1N HCl (10 mL), brine (10 mL), dried over MgS04, filtered and concentrated in vacuo to give the title compound. (M+H)+ = 150.
Example 27 F
Me0 O
CN
To a solution of bis(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate (0.875 mL, 4.14 mmol) and 18-crown-6 (5.46 g, 20.7 mmol) in THF (20 mL) at -78°C, was added potassium bis(trimethylsilyl)amide (8.3 mL, 4.15 mmol) dropwise.
After the addition was complete, compound of example 26 (616 mg, 4.14 mmol) in THF (10 mL) was added. The mixture was stirred at -78°C for 1 hour.
Aqueous NH4C1 solution was added to quench the reaction. Water and EtOAc was added to the mixture. The organic layer was dried over MgS04, filtered and concentrated in vacuo. This was purified by silica gel column chromatography using solvent system 20% EtOAc in hexane as eluant to give the title compound (375 mg, 44%). ES-MS
(M+H)+ = 206.1.
Example 28 F
'-' O
S02NHtBu CN
To a solution of compound of example 22 (553 mg, 1.82 mmol) in DCM (9 mL) was added trimethylaluminum (2.73 mL, 2M in hexane, 5.46 mmol) dropwise. The reaction mixture was stirred at room temperature for 1 hour. Compound of example 27 (373 mg, 1.82 mmol) in DCM (5 mL) was added dropwise. The mixture was stirred at room temperature overnight. 2N HCl was added to pH 2. Water and DCM
were added. The organic layer was dried over MgS04 and concentrated in vacuo.
It was purified by silica gel column chromatography using solvent system 50%
EtOAc in hexane as eluant to give the title compound (283 mg). ES-MS (M+Na)+ =
500.1.
Example 29 F
O
S02NHtBu A solution of the compound of example 28 (283 mg, 0.593 mmol) in MeOH (10 mL) was treated with a stream of HCl gas for 10 min. at 0°C. The resulting solution was capped, stirred at room temperature overnight and evaporated in vacuo. The residue was reconstituted in MeOH (10 mL) and the mixture was treated with NH40Ac (228 mg, 2.97 mmol). The reaction mixture was refluxed for 2 hrs. and concentrated in vacuo. The obtained residue was purified by RP-HPLC to give the title compound as a white powder. ES-MS (M+H)+ = 439.1.
Example 30 F
O
S02NHtBu Compound of example 29 (12 mg, 0.027 mmol) was dissolved in MeOH (5 mL) and 10% PdIC (catalytic amount) was added. The mixture was hydrogenated under balloon. overnight, filtered through Celite to remove the catalyst and the filtrate was evaporated. The obtained residue was purified by RP-HPLC to give the title compound as a white powder. ES-MS (M+H)+ = 441.1.
Example 31 Ho OMe CN
To a solution of methyl-3-cyano-4-methoxybenzoate (5g, 26.2 mmol) in THF (50 mL) was added lithium borohydride (53 mL, 2.00M solution in THF, 105 mmol) at room temperature. The mixture was stirred at room temperature overnight. IN
HCl was slowly added until bubbling stopped. THF was removed in vacuo and EtOAc and water were added. The organic layer was washed with water, saturated NaHC03 solution, brine, dried with NazS04 and solvent evaporated in vacuo to give the title compound (3.7 g, 86.7%).
Example 32 O
OMe CN
To a solution of compound of example 31 (2g, 12.3 mmol) in DMSO (50 mL) was added IBX (4.673g, 17.7 mmol) slowly. The mixture was stirred at room temperature overnight. EtOAc and water were added. The formed precipitate was removed. The organic layer was washed with 1N HCI, water, saturated NaHC03, brine, dried over NazS04 and concentrated in vacuo. The obtained residue was purified by silica gel column chromatography using DCM as eluant to give the title compound (1.1g, 56%). ES-MS (M+H)+= 162.1.
Example 33 Me0 O I/
home CN
To a solution of bis(2,2,2-trifluoroethyl)(methoxycarbonylmethyl) phosphonate (1.39 mL, 6.57 mmol) in THF (130 mL) at -78°C was added 18-crown-6 (8.6, 33.9 mmol), potassium bis(trimethylsilyl)amide (14.4 mL, 7.22 mmol) dropwise. The mixture was stirred at at -78°C for 30 min. Compound of example 32 (1.06 g, 6.57 mmol) was then added. The mixture was warmed to room temperature and stirred for 1 hour. Aqueous NH4C1 solution was added to quench the reaction.
Water and EtOAc was added to the mixture. The organic layer was dried over MgS04, filtered and concentrated in vacuo to give the title compound (1.175g, 87%).
ES-MS (M+H)+ = 218.1.
Exam lie 34 / \ / \ N I w O home S02NHtBu CN
To a solution of compound of example 22 (457 mg, 1.5 mmol) in DCM (4 mL) was added trimethylaluminum (0.9 mL, 2M in hexane, 1.8 mmol) dropwise. The reaction mixture was stirred at room temperature for 1 hour. Compound of example 33 (326 mg, 1.5 mmol) in DCM (5 mL) was added dropwise. The mixture was heated to reflux briefly. 1N HCl was added to pH 2. Water and DCM were added.
The organic layer was washed with brine, dried over MgS04 and concentrated in vacuo. It was purified by silica gel column chromatography using solvent system 30-50% EtOAc in hexane as eluant to give the title compound (450 mg, 61.3%).
ES-MS (M+H)+ = 490.1.
Example 35 / \ / \
O ~ OMe S02NHz A solution of the compound of example 34 (200 mg, 0.408 mmol) in MeOH (10 mL) was treated with a stream of HCl gas for 10 min. at 0°C. The resulting solution was capped, stirred at room temperature overnight and evaporated in vacuo. The residue was reconstituted in MeOH (10 mL) and the mixture was treated with NH40Ac (650 mg, 8.16 mmol). The reaction mixture was refluxed for 2 hrs. and concentrated in vacuo. The obtained residue was purified by RP-HPLC to give the title compound as a white powder. ES-MS (M+H)+ = 451.1.
Example 36 / \ / \
O ~ OMe Compound of example 35 (6 mg, 0.027 mmol) was dissolved in MeOH (2 mL) and 10% Pd/C (catalytic amount) was added. The mixture was hydrogenated under balloon overnight, filtered through Celite to remove the catalyst and the filtrate was evaporated to give the title compound as a white powder. ES-MS (M+H)+ = 443.1.
Example37 H NHBoc \ / \
'~ O i S02NHtBu CN
Boc-m-CN-Phenylalanine -OH (200 mg, 0.69 mmol) and compound of example 22 (210 mg, 0.69 mmol) were dissolved in DMF (3 mL). DIEA (0.24 mL, 1.4 mmol) was added followed by the addition of the coupling reagent PyBOP (572 mg, 1.1 mmol). The solution was stirred at room temperature for 12 hours. The reaction mixture was diluted in a mixture of EtOAc/HzO. The organic layer was washed with water, saturated NazC03, water, 1M KHS04, brine, dried over MgS04, filtered and solvent evaporated to give the title compound. ES-MS (M+H)+ = 521.1.
Example 38 / \ /
O
A solution of the compound of example 37 (132 mg, 0.23 mmol) in MeOH (10 mL) was treated with a stream of HCl gas for 10 min. at 0°C. The resulting solution was capped, stirred at room temperature overnight and evaporated in vacuo. The residue was reconstituted in MeOH (10 mL) and the mixture was treated with NH40Ac (540 mg, 7 mmol). The reaction mixture was refluxed for 2 hrs. and concentrated in vacuo. The obtained residue was purified by RP-HPLC to give the title compound as a white powder. ES-MS (M+H)+ = 438.1.
Example 39:
Tf0 C02Et To a solution of ethyl 2-oxocyclopentane carboxylate (1.56g, lOmmol) in 20m1 anhydrous dichloromethane was added triethylamine (1.06g, 10.5mmo1). Reaction was cooled under argon to -78°C to which trifluoro-methanesulfonic anhydride (2.96g, 10.5mmo1) was added dropwise via syringe over S minutes. Reaction was allowed to warm to room temperature and stirred over night. Next morning the reaction was diluted with 25m1 dichloromethane, organic was washed with 2xSOm1 water, 2xSOml 1N HCI, dried over magnesium sulfate, filtered and concentrated to give ethyl 2- f [(trifluoromethyl)sulfonyl]oxy}-1-cyclopentene-1-carboxylate (2.8g, 97%) as a light brown oil after drying. H'NMR (CDC13) : 1.27 -1.56 (t, 3H);
1.97-2.01 (m, 2H); 2.6-2.74 (m, 4H); 4.21-4.26 (m, 2H).
Example 40:
CN
To a solution of ethyl 2-{[(trifluoromethyl)sulfonyl]oxy}-1-cyclopentene-1-carboxylate (1.2g, 4.16mmol) in lOml anhydrous dioxane was added potassium phosphate (1.32g, 6.2mmol), 3-cyanophenyl boronic acid (0.612g, 4.16mmo1), and tetrakis (triphenylphosphine)palladium(0) (0.12g, O.lOmmol). Reaction mixture was heated to reflux and stirred overnight. Mixture was filtered through a pad of Celite, diluted with 50m1 ethyl acetate, washed with 2x50m1 water, 2x50m1 saturated brine solution, dried over magnesium sulfate, filtered and concentrated in vacuo.
Residue was chromatographed on silica gel using 5% EtOAc in hexane as the eluent to give ethyl 2-(3-cyanophenyl)-1-cyclopentene-1-carboxylate (0.7g, 71%) as a light yellow oil after drying. ES-MS (M+H+): 242.15. H'NMR (CDC13) : 1.09-1.13 (t, 3H);
1.96-2.01 (m, 2H); 2.80-2.84 (m, 4H); 7.39-7.59 (m, 4H).
Example 41:
HzN O
O=S~
H
N
H2N rvn To a solution of 2'-tert-butylaminosulfonyl-4-amino-[1,1']-biphenyl (60mg, 0.197mmo1) in 4m1 anhydrous dichloromethane was added a solution of 2M
trimethylaluminum in hexane (0.3m1, 0.59mmo1). Reaction was stirred at room temperature for 20 minutes to which a solution of ethyl 2-(3-cyanophenyl)-1-cyclopentene-1-carboxylate (48mg, 0.197mmol) in lml anhydrous dichloromethane.
Reaction was stirred at room temperature overnight. Reaction was quenched with 15m1 1N HCl after which an additional lOml dichloromethane was added. Organic was washed with 2x20m1 water, dried over magnesium sulfate and concentrated to give N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl][2-(3-cyanophenyl)cyclopent-1-enyl]carboxamide (80mg, 80%) as a white powder which was sufficiently pure to be used without further purification.
To a solution ofN-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl][2-(3-cyanophenyl)cyclopent-1-enyl]carboxamide (70mg, 0.137mmo1) in 5m1 anhydrous methanol cooled in an ice bath was bubbled HCl gas until saturation was achieved.
Reaction was allowed to warm to room temperature and stirred overnight. The reaction was then concentrated in vacuo and dried under hi vacuum. The dried residue was dissolved in 5m1 anhydrous methanol to which ammonium acetate (77mg, lmmol) was added and the reaction heated to reflux for 2 hours. The reaction was concentrated and purified on a 2x25cm Vydac C,g HPLC column to give 3-(2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}cyclopent-1-enyl)benzenecarboxamidine (40mg, 63%) as a fluffy white powder after lyophilization. ES-MS (M+H+): 461.15 S
Example 42:
HZN O
O=S~
H
N
H2N rvn To a solution of the 3-(2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}cyclopent-enyl)benzenecarboxamidine (7mg, O.Ol5mmol) in 4m1 methanol was added 10% Pd on carbon (l.Smg). Mixture was treated with SOpsi hydrogen on the PARK
apparatus for lhr. Reaction was filtered through a pad of Celite, concentrated and lyophilized to give the 3-(2-{N-[4-(2-sulfamoylphenyl)phenyl]-carbamoyl}cyclopentyl)benzenecarboxamidine (Smg, 71%) as a fluffy white powder. ES-MS (M+H+): 463.15 Example 43:
C02Et Tf0 C02Et Tf0 To a solution of ethylacetoacetate (1.3g, lOmmol) in lOml anhydrous dichloromethane was added triethylamine (1.46m1, 10.5mmo1). The reaction was cooled to -78°C under argon to which trifluoromethanesulfonic anhydride (2.96g, lO.Smmo1) was added dropwise via syringe over 5 minutes. Reaction was allowed to warm to room teperature and stirred over night. Next morning the reaction was diluted with 25m1 dichloromethane, organic was washed with 2x50m1 water, 2x50m1 1N HCI, dried over magnesium sulfate, filtered and concentrated. Crude oil was chromatographed on silica gel using 5% EtOAc in hexane as the eluent to give 1) ethyl (E)-3-{[(trifluoromethyl)sulfonyl]-oxy}-2-propenoate (800mg, 60%) as a clear oil: H'NMR (CDCl3) : 1.247-1.282 (t, 3H); 2.471 (s, H); 4.155-4.209 (m, 2H);
S 5.912 (s, H); and 2) ethyl (Z)-3-{[(trifluoromethyl)sulfonyl]-oxy}-2-propenoate (450mg, 30%) as a clear oil: H'NMR (CDCl3) : 1.247-1.283 (t, 3H); 2.131 (s, 3H);
4.18-4.233 (m, 2H); 5.736 (s, H).
Example 44:
CN
To a solution of ethyl (E)-3-{[(trifluoromethyl)sulfonyl]-oxy}-2-propenoate (390mg, 1.49mmo1) in Sml anhydrous dioxane was added potassium phosphate (474mg, 2.24mmo1), 3-cyanophenyl boronic acid (217mg, 1.49mmol), and tetrakis (triphenylphosphine)palladium(0) (43mg, 0.038mmol). Reaction mixture was heated to reflux and stirred overnight. Mixture was filtered through a pad of Celite, diluted with SOmI ethyl acetate, washed with 2x50m1 water, 2x50m1 saturated brine solution, dried over magnesium sulfate, filtered and concentrated in vacuo.
Residue was chromatographed on silica gel using 5% EtOAc in hexane as the eluent to give ethyl (E) 3-(3-cyanophenyl)-2-propenoate (240mg, 71%) as a clear yellow oil after drying. H'NMR (CDC13) : 1.2-1.32 (t, 3H); 2.547 (s, 3H); 4.18-4.24 (m, 2H);
6.113 (s, H); 7.47-7.725 (m, 4H). NOE confirmed stereo orientation.
Example 45:
~02Et CN
To a solution of ethyl (Z)-3-{[(trifluoromethyl)sulfonyl]-oxy}-2-propenoate (330mg, 1.25mmo1) in Sml anhydrous dioxane was added potassium phosphate (398mg, 1.88mmo1), 3-cyanophenyl boronic acid (185mg, 1.25mmol), and tetrakis (triphenylphosphine)palladium(0) (36mg, 0.031mmol). Reaction mixture was heated to reflux and stirred overnight. Mixture was filtered through a pad of Celite, diluted with SOmI ethyl acetate, washed with 2x50m1 water, 2x50m1 saturated brine solution, dried over magnesium sulfate, filtered and concentrated in vacuo.
Residue was chromatographed on silica gel using 5% EtOAc in hexane as the eluent to give ethyl (Z) 3-(3-cyanophenyl)-2-propenoate (240mg, 71 %) as a clear oil after drying.
ES-MS (M+H+): 216.05 Example 46:
O=S~
O
H2N rvn To a solution of 2'-tert-butylaminosulfonyl-4-amino-[1,1']-biphenyl (79mg, 0.26mmol) in 4m1 anhydrous dichloromethane was added a solution of 2M
trimethylaluminum in hexane (0.39m1, 0.78mmo1). Reaction was stirred at room temperature for 20 minutes to which a solution of ethyl (E) 3-(3-cyanophenyl)-propenoate (56mg, 0.26mmo1) in lml anhydrous dichloromethane was added.
Reaction was stirred at room temperature overnight. Reaction was quenched with Sml 1N HCl after which an additional lOml dichloromethane was added. Organic layer was washed with 2x20m1 water, dried over magnesium sulfate, filtered and concentrated to give the (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)but-2-enamide (90mg, 72%) as an off white powder which was sufficiently pure to be used without further purification.
To a solution of (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)but-2-enamide (90mg, 0.19mmo1) in Sml anhydrous methanol cooled in an ice bath was bubbled HCl gas until saturation was achieved. Reaction was allowed to warm to room temperature and stirred overnight. The reaction was then concentrated in vacuo and dried under hi vacuum. The dried residue was dissolved in Sml anhydrous methanol to which ammonium acetate (77mg, lmmol) was added and the reaction heated to reflux for 2 hours. The reaction was concentrated and purified on a 2x25cm Vydac C,g HPLC column to give 3-((lE)-1-methyl-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}vinyl)benzene-carboxamidine (l5mg, 20%) as a fluffy white powder after lyophilization. ES-MS (M+H+): 435.1 Example 47:
a ~~
H
N
H2lv rvn To a solution of 2'-tert-butylaminosulfonyl-4-amino-[1,1']-biphenyl (198mg, 0.65mmo1) in Sml anhydrous dichloromethane was added a solution of 2M
trimethylaluminum in hexane (0.98m1, 1.95mmol). Reaction was stirred at room temperature for 20 minutes to which a solution of ethyl (Z) 3-(3-cyanophenyl)-propenoate (140mg, 0.65mmol) in lml anhydrous dichloromethane was added.
Reaction was stirred at room temperature overnight. Reaction was quenched with Sml 1N HCl after which an additional 20m1 dichloromethane was added. Organic was washed with 2x25m1 water, dried over magnesium sulfate and concentrated to give (2Z)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)but-2-enamide (200mg, 65%) as a light brown residue which was sufficiently pure to be used without further purification.
To a solution of (2Z)-N-[4-(2-{[(tent-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)but-2-enamide (90mg, 0.19mmo1) in Sml anhydrous methanol cooled in an ice bath was bubbled HCl gas until saturation was achieved. Reaction was allowed to warm to room temperature and stirred overnight. The reaction was then concentrated in vacuo and dried under hi vacuum. The dried residue was dissolved in Sml anhydrous methanol to which ammonium acetate (144mg, 2mmo1) was added and the reaction heated to reflux for 2 hours. The reaction was concentrated and purified on a 2x25cm Vydac C,$ HPLC column to give 3-((1Z)-1-methyl-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}vinyl)-benzenecarboxamidine (35mg, 20%) as a fluffy white powder after lyophilization. ES-MS (M+H+): 435.1 Example 48:
a H
N
HZIv nn To a solution of the 3-((1Z)-1-methyl-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}vinyl)-benzenecarboxamidine (Smg, 0.01 l5mmol) in 4m1 methanol was added 10% Pd on carbon (2mg). Mixture was treated with SOpsi hydrogen on the PARK apparatus for lhr. Reaction was filtered through a pad of Celite, concentrated and lyophilized to give 3-(1-methyl-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}-ethyl)benzenecarboxamidine (3mg, 60%) as a fluffy white powder. ES-MS (M+H+): 437.1 Example 49:
Tf0 C02Et To a solution of ethyl trifluoroacetoacetate (5g, 27.2mmo1) in 20m1 anhydrous dichloromethane was added triethylamine (5.7m1, 40.7mmo1). Reaction was cooled . under argon to -78°C to which trifluoro-methanesulfonic anhydride (ll.Sg, 10.5mmo1) was added dropwise via syringe over 5 minutes. Reaction was allowed to warm to room temperature and stirred over night. Next morning the reaction was diluted with 25m1 dichloromethane, organic was washed with 2x50m1 water, 2x50m1 1N HCI, dried over magnesium sulfate, filtered and concentrated in vacuo.
Crude oil was chromatographed on silica gel using 5% EtOAc in hexane as the eluent to give ethyl (Z)-4,4,4-trifluoro-3-{[(trifluoromethyl)sulfonyl]-oxy}-2-butenoate (7.7g, 90%) as a clear light yellow oil after drying. H'NMR (CDC13) . 1.31-1.35 (t, 3H);
4.33-4.35 (m, 2H); 6.535 (s, H).
Example 50:
C02Et CN
To a solution of ethyl (Z)-4,4,4-trifluoro-3-{[(trifluoromethyl)sulfonyl]-oxy}-butenoate (250mg, 0.79mmo1) in Sml anhydrous dioxane was added potassium phosphate (251mg, 1.19mmo1), 3-cyanophenyl boronic acid (116mg, 0.79mmo1), and tetrakis (triphenylphosphine)palladium(0) (23mg, 0.02mmo1). Reaction mixture was heated to reflux and stirred overnight. Mixture was filtered through a pad of Celite, diluted with SOmI ethyl acetate, washed with 2x50m1 water, 2x50m1 saturated brine solution, dried over magnesium sulfate, filtered and concentrated in vacuo.
Residue was chromatographed on silica gel using 20% EtOAc in hexane as the eluent to give ethyl (2E)-3-(3-cyanophenyl)-4,4,4-trifluorobut-2-enoate (150mg, 79%) as a yellow residue after drying. H'NMR (CDC13) : 1.107-1.142 (t, 3H);
4.05-4.107 (m, 2H); 6.684 (s, H); 7.38-7.72 (m, 4H).
Example 51:
HZN
O=S O
H
N
HZw nn To a solution of 2'-tert-butylaminosulfonyl-4-amino-[1,1']-biphenyl (79mg, 0.26mmo1) in 5m1 anhydrous dichloromethane was added a solution of 2M
trimethylaluminum in hexane (0.39m1, 0.78mmo1). Reaction was stirred at room temperature for 20 minutes to which a solution of ethyl (Z) 3-(3-cyanophenyl)-4,4,4-trifluoro-2-butenoate (70mg, 0.26mmo1) in lml anhydrous dichloromethane was added. Reaction was stirred at room temperature overnight. Reaction was quenched with 5m1 1N HCl after which an additional 20m1 dichloromethane was added.
Organic was washed with 2x25m1 water, dried over magnesium sulfate, filtered and concentrated to give (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)pheriyl]-3-(3-cyanophenyl)-4,4,4-trifluorobut-2-enamide (120mg, 88%) as a yellow foam which was sufficiently pure to be used without further purification.
To a solution of (2E)-N-[4-(2-{[(tent-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)-4,4,4-trifluorobut-2-enamide (90mg, 0.19mmo1) in lOml 1:1 ethyl acetate:anhydrous methanol cooled to -78°C was bubbled HCl gas until saturation was achieved. Reaction was placed in the refrigerator at 0°C over the weekend.
The reaction was then concentrated in vacuo and dried under hi vacuum. The dried methyl imidate residue was dissolved in 5m1 anhydrous methanol to which ammonium acetate (144mg, 2mmo1) was added and the reaction heated to reflex for 2 hours. The reaction was concentrated then treated with lOml trifluoroacetic acid for 2hrs, concentrated and purified on a 2x25cm Vydac C,8 HPLC column to give (( 1 E)-2- {N-[4-(2-sul famoylphenyl)phenyl] carbamoyl } -1-(trifluoromethyl)vinyl)benzenecarboxamidine (57mg, 47%) as a fluffy white powder after lyophilization. ES-MS (M+H+): 489.15 Example 52:
u_~
H
N
H2W nn To a solution of 3-((lE)-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}-1-(trifluoromethyl)vinyl)-benzenecarboxamidine (lOmg, 0.02mmo1) in 4m1 methanol was added 10% Pd on carbon (2mg). Mixture was treated with hydrogen at 1 atmosphere under balloon for lhr. Reaction was filtered through a pad of Celite, concentrated and lyophilized to give 3-[2,2,2-trifluoro-1-({N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}-methyl)ethyl]benzenecarboxamidine (8mg, 82%) as a fluffy white powder. ES-MS (M+H+): 491.1 Example 53:
/C02Et CN
To a solution of ethyl (Z) 3-(3-cyanophenyl)-2-propenoate (2g, 9.3mmo1) in SOmI
carbon tetrachloride was added N-bromosuccinimide (1.748, 9.77mmo1) and benzoyl peroxide (40mg, 0.165mmo1). Reaction mixture was heated to reflux and stirred over night. Reaction was allowed to cool to room temperature to which SOmI
dichloromethane was added. Organic was washed with 2x50m1 water, dried over magnesium sulfate, filtered and concentrated in vacuo. Crude residue was chromatographed on silica gel using 2.5% EtOAc in hexane as the eluent to give ethyl (Z) 3-(3-cyanophenyl)-4-bromo-2-butenoate (0.77g, 29%) as a clear oil (note:
NOE experiment showed compound isomerized during bromination). H'NMR
(CDC13) : 1.311-1.347 (t, 3H); 4.239-4.292 (m, 2H); 4.92 (s, 2H); 6.18 (s, H);
7.514-7.801 (m, 4H). ES-MS (M+H+): 293.95 and 296.0 Example 54:
C02Et N~N
To a solution of ethyl (Z) 3-(3-cyanophenyl)-4-bromo-2-butenoate (103mg, 0.35mmo1) in Sml anhydrous di-methylformamide was added pyrazole (24mg, 0.35mmo1) and cesium carbonate (228mg, 0.7mmo1). Reaction mixture was stirred for 1.5 hours at room temperature after which 25m1 ethyl acetate was added.
S Organic was washed with 3x25m1 water, 3x50m1 saturated brine solution, dried over magnesium sulfate, filtered and concentrated to give ethyl (Z)-3-(3-cyanophenyl)-4-(1H 1-pyrazolyl)-2-butenoate (70mg, 71%) as a brown residue which was sufficiently pure to be used without further purification. ES-MS (M+H+): 282.1 Example SS:
a ~i NON n N
H
To a solution of 2'-tert-butylaminosulfonyl-4-amino-[1,1']-biphenyl (76mg, 0.25mmo1) in 4m1 anhydrous dichloromethane was added a solution of 2M
trimethylaluminum in hexane (0.38m1, 0.75mmo1). Reaction was stirred at room temperature for 20 minutes to which a solution of ethyl (Z)-3-(3-cyanophenyl)-(1H 1-pyrazolyl)-2-butenoate (70mg, 0.25mmo1) in lml anhydrous dichloromethane was added. Reaction was stirred at room temperature overnight. Reaction was quenched with Sml 1N HCl after which an additional 20m1 dichloromethane was added. Organic was washed with 2x20m1 water, dried over magnesium sulfate and concentrated to give the tButyl nitrile of the title compound (120mg, 89%) as a brown foam which was sufficiently pure to use in the next step.
To a solution of the above nitrite compound (120mg, 0.22mmo1) in lOml 1:1 ethyl acetate : anhydrous methanol cooled to -78°C was bubbled HCl gas until saturation was achieved. Reaction was allowed to warm to room temperature and stirred overnight. The reaction was then concentrated in vacuo and dried under hi vacuum.
The dried methyl imidate residue was dissolved in Sml anhydrous methanol to which ammonium acetate (77mg, lmmol) was added and the reaction heated to reflux for 2 hours. The reaction was concentrated, then treated with trifluoroacetic acid (lOml) for 2 hours, concentrated and purified on a 2x25cm Vydac C,8 HPLC
column to give 3-((1Z)-1-(pyrazolylmethyl)-2-{N-[4-(2-sulfamoylphenyl)phenyl]-carbamoyl}vinyl)benzenecarboxamidine (lOmg, 9%) as a fluffy white powder after lyophilization. ES-MS (M+H+): 501.1 Example 56:
N~ 1 vN
O
CN
To a solution of 3-acetobenzonitrile (5g, 0.0344mo1) in 45m1 glacial acetic acid was added pyridinium tribromide (11.3g, 0.0355mo1). Reaction was stirred at room temperature under argon overnight. Reaction was then quenched with a saturated sodium sulfite solution (20m1) and extracted with 3x25m1 dichloromethane.
Combined organic phases were washed with 2x25m1 water, dried over magnesium sulfate, filtered and concentrated in vacuo. Crude oil was chromatographed on silica gel using 5% EtOAc in hexane as the eluent to give 3-(2-bromoacetyl) benzonitrile (4.5g, 58%) as a white solid. H'NMR (CDCl3) : 4.371-4.403 (s, 2H); 7.613-7.664 (m, H); 7.838-7.888 (m, H); 8.192-8.261 (m, 2H).
To a solution of 3-(2-bromaceto)benzonitrile (SOOmg, 2.23mmo1) in Sml dichloromethane was added pyrazole (304mg, 4.46mmo1) and triethylamine (0.31m1, 2.23mmol). Reaction was stirred at room temperature over night. Reaction was then diluted with 20m1 dichloromethane, washed with 2x25m1 water, 2x25m1 1N
HCI, dried over magnesium sulfate, filtered and concentrated in vacuo. Crude residue was chromatographed on silica gel using 2.5% EtOAc in hexane to give 3-[2-(IH 1-pyrazolyl)acetyl]benzonitrile (330mg, 70%) as a clear oil after drying. ES-MS (M+H+): 212.05 Example 57:
~02Me To a solution of bis(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate (0.39m1, 1.87mmol) in Sml anhydrous tetrahydrofuran was added a solution of 18-crown-6 (2g, 7.8mmo1) in Sml anhydrous tetrahydrofuran. Reaction was cooled to -78° C to which a O.SM solution of potassium bis(trimethylsilyl)amide in toluene (0.93m1, 1.87mmol) was added all at once. The reaction mixture was stirred at -78°
C for 20 minutes after which a solution of 3-[2-(1H 1-pyrazolyl)acetyl]-benzonitrile (330mg, 1.56mmo1) in Sml anhydrous tetrahydrofuran was added dropwise over several minutes. Reaction was gradually allowed to warm to room temperature and stirred for S hours. Reaction was then quenched with a saturated ammonium chloride solution (lOml) and extracted with 2x25m1 diethyl ether. Combined organic layers were washed with 2x25m1 water, 2x25m1 saturated brine solution, dried over magnesium sulfate, filtered and concentrated to a brown residue.
Crude residue was chromatographed on silica gel using a gradient of 5% EtOAc in hexane containing 0.1 % triethylamine to 20% EtOAc in hexane contaning 0.1 N~
triethylamine to give methyl (E)-3-(3-cyanophenyl)-4-(1H 1-pyrazolyl)-2-butenoate (135mg, 32%) as a clear oil after drying. H'NMR (CDC13) : 3.521 (s, #H); 4.98 (s, 2H); 5.694 (s, H); 6.237-6.247 (t, H); 7.296-7.593 (m, 6H). NOE experiment confirmed stereoconfiguration.
Example 58:
N ~ a ~i N
H
N
HZIv rvn To a solution of 2'-tert-butylaminosulfonyl-4-amino-[1,1']-biphenyl (lOSmg, 0.34mmo1) in 4m1 anhydrous dichloromethane was added a solution of 2M
trimethylaluminum in hexane (O.SmI, 1.02mmo1). Reaction was stirred at room temperature for 20 minutes to which a solution of methyl (E)-3-(3-cyanophenyl)-(1H 1-pyrazolyl)-2-butenoate (90mg, 0.34mmo1) in lml anhydrous dichloromethane was added. Reaction was stirred at room temperature overnight. Reaction was quenched with Sml 1N HCl after which an additional 20m1 dichloromethane was added. Organic was washed with 2x20m1 water, dried over magnesium sulfate, filtered and concentrated to give (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)but-2-enamide (155mg, 85%) as an off white foam which was sufficiently pure to be used without further purification.
To a solution of (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)but-2-enamide (155mg, 0.287mmol) in lOml 1:1 ethyl acetate:anhydrous methanol cooled to -78°C was bubbled HCl gas until saturation was achieved. Reaction was allowed to warm to room temperature and stirred overnight. The reaction was then concentrated in vacuo and dried under hi vacuum.
The dried methyl imidate residue was dissolved in Sml anhydrous methanol to which ammonium acetate (77mg, lmmol) was added and the reaction heated to reflux for 2 hours. The reaction was concentrated, treated with trifluoroacetic acid S (lOml) for 2hrs, concentrated and purified on a 2x25cm Vydac C,$ HPLC column to give 3-((lE)-1-(pyrazolylmethyl)-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}vinyl)benzenecarboxamidine (40mg, 28%) as a fluffy white powder after lyophilization. ES-MS (M+H+): 501.1 Example 59:
N ~ H2N
O
N ~ O S~
H
N
H2lv rv n To a solution of 3-((lE)-1-(pyrazolylmethyl)-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}vinyl)-benzenecarboxamidine (Smg, O.Olmmol) in 4m1 methanol was added 10% Pd on carbon (lmg). Mixture was treated with hydrogen at 1 atmosphere under balloon for lhr. Reaction was filtered through a pad of Celite, concentrated and lyophilized to give 3-(1-(pyrazolylmethyl)-2-f N-[4-(2-sulfamoylphenyl)phenyl]-carbamoyl}ethyl)benzenecarboxamidine (Smg, 100%) as a fluffy white powder. ES-MS (M+H+): 503.1 Example 60:
2Et To a solution of ethyl B-oxo-3-furanpropionate (1g, 5.49mmo1) in Sml anhydrous dichloromethane was added triethylamine (0.847m1, 6.04mmo1). Reaction was cooled under argon to -78°C to which trifluoromethanesulfonic anhydride (1.02m1, 6.04mmo1) was added dropwise via syringe over 5 minutes. Reaction was allowed to warm to room temperature and stirred over night. Next morning the reaction was diluted with 25m1 dichloromethane, organic was washed with 2x50m1 water, 2x50m1 1N HCI, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude oil was chromatographed on silica gel using 20% EtOAc in hexane as the eluent to give ethyl (Z)-3-(2-furyl)-3-{[(trifluoromethyl)sulfonyl]-oxy}-2-propenoate (1.6g, 93%) as a light brown solid after drying. H'NMR (CDC13) :
1.31-1.35 (t, 3H); 4.26-4.314 (m, 2H); 6.065 (s, H); 6.522 (s, H); 7.47 (s, H);
7.76 (s, H).
Example 61:
~OZEt CN
To a solution of ethyl (Z)-3-(2-furyl)-3-{[(trifluoromethyl)sulfonyl]-oxy}-2-propenoate (SOOmg, 1.59mmo1) in 7m1 anhydrous dioxane was added potassium phosphate (506mg, 2.4mmo1), 3-cyanophenyl boronic acid (234mg, 1.59mmo1), and tetrakis (triphenylphosphine)palladium(0) (46mg, 0.04mmo1). Reaction mixture was heated to reflux and stirred overnight. Mixture was filtered through a pad of Celite, diluted with SOmI ethyl acetate, washed with 2xSOm1 water, 2x50m1 saturated brine solution, dried over magnesium sulfate, filtered and concentrated in vacuo.
The crude residue was chromatographed on silica gel using a gradient from 5% EtOAc in hexane to 10% EtOAc in hexane as the eluent to give ethyl (E) 3-(3-cyanophenyl)-3-(2-furyl)-2-propenoate (100mg, 24%) as a clear yellow oil after drying. H'NMR
(CDC13) : 1.1-1.14 (t, 3H); 4,016-4.035 (m, 2H); 5.293 (s, H); 7.45-7.549 (m, 3H);
7.669 (m, H). ES-MS (M+H+): 268.05 Example 62:
HzN O
O=S~
H
N
To a solution of 2'-tButylaminosulfonyl-4-amino-[1,1']-biphenyl (102mg, 0.336mmo1) in 4m1 anhydrous dichloromethane was added a solution of 2M
trimethylaluminum in hexane (O.SmI, 1.Ommo1). Reaction was stirred at room temperature for 20 minutes to which a solution of ethyl (E) 3-(3-cyanophenyl)-3-(2-furyl)-2-propenoate (90mg, 0.336mmo1) in lml anhydrous dichloromethane was added. Reaction was stirred at room temperature overnight. Reaction was quenched with Sml 1N HCl after which an additional 20m1 dichloromethane was added.
Organic was washed with 2x20m1 water, dried over magnesium sulfate and concentrated to give (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)-3-(2-furyl)prop-2-enamide (200mg, 112%) as a brown foam which was sufficiently pure to be used without further purification.
To a solution of (2E)-N-[4-(2-{[(tent-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)-3-(2-furyl)prop-2-enamide (176mg, 0.336mmol) in lOml 1:1 ethyl acetate:anhydrous methanol cooled to -78°C was bubbled HCl gas until saturation was achieved. Reaction was allowed to warm to room temperature and stirred overnight. The reaction was then concentrated in vacuo and dried under hi vacuum.
The dried methyl imidate residue was dissolved in Sml anhydrous methanol to which ammonium acetate (144mg, 2mmo1) was added and the reaction heated to reflux for 2 hours. The reaction was concentrated, treated with trifluoroacetic acid (lOml) for 2hrs, concentrated and purified on a 2x25cm Vydac C,g HPLC column to give 3-((lE)-1-(2-furyl)-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}vinyl)benzenecarboxamidine (60mg, (37%) as a fluffy off white powder after lyophilization. ES-MS (M+H+): 487.15 Example 63:
HZN
O=S O
H
N
To a solution of 3-((lE)-1-(2-furyl)-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}vinyl)benzenecarboxamidine (lOmg, 0.02mmo1) in 4m1 methanol was added 10% Pd on carbon (2mg). Mixture was treated with hydrogen at 1 atmosphere under balloon for lhr. Reaction was filtered through a pad of Celite, concentrated and lyophilized to give 3-(1-(2-fiuyl)-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}ethyl)benzenecarboxamidine (9mg, 90%) as a fluffy white powder. ES-MS (M+H+): 489.15 Example 64:
OMe Tf0 C02Me To a solution of methyl 4-methoxy-3-oxobutanoate (5g, 34.2mmo1) in 20m1 anhydrous dichloromethane was added triethylamine (5.24m1, 37.6mmo1). Reaction was cooled under argon to -78°C to which trifluoromethane-sulfonic anhydride (10.6gm1, 37.6mmo1) was added dropwise via syringe over 5 minutes. Reaction was allowed to warm to room temperature and stirred over night. Next morning the reaction was diluted with 25m1 dichloromethane, organic was washed with 2x50m1 water, 2x50m1 1N HCI, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude oil was chromatographed on silica gel using a gradient of 5%
EtOAc in hexane to 10% EtOAc in hexane as the eluent to give methyl (Z)-4-methoxy-3- f [(trifluoromethyl)sulfonyl]-oxy}-2-butenoate (5.1g, 54%) as a clear colorless oil after drying. H'NMR (CDC13) : 3.342 (s, 3H); 3.711 (s, 3H); 3.99 (s, H); 6.02 (s, H).
Example 65:
~OZMe CN
To a solution of methyl (Z)-4-methoxy-3-{[(trifluoromethyl)sulfonyl]-oxy}-2-butenoate (246mg, l.Ommo1) in Sml anhydrous dioxane was added potassium phosphate (318mg, l.Smmol), 3-cyanophenyl boronic acid (162mg, l.Ommo1), and tetrakis (triphenylphosphine)palladium(0) (29mg, 0.0251mmo1). Reaction mixture was heated to reflux and stirred overnight. Mixture was filtered through a pad of Celite, diluted with 20m1 ethyl acetate. Organic was washed with 2x20m1 water, 2x20m1 saturated brine solution, dried over magnesium sulfate, filtered and concentrated in vacuo to give methyl (E)-3-(3-cyanophenyl)-4-methoxy-2-butenoate (220mg, 75%) as a clear brown oil which was sufficiently pure to be used without further purification. ES-MS (M+H+): 232.1 Example 66:
O
OMe O S
H
N
H2N rvn To a solution of 2'-tButylaminosulfonyl-4-amino-[1,1']-biphenyl (lOSmg, 0.35mmo1) in 4m1 anhydrous dichloromethane was added a solution of 2M
trimethylaluminum in hexane (0.53m1, I.OSmmo1). Reaction was stirred at room temperature for 20 minutes to which a solution of methyl (E) 3-(3-cyanophenyl)-methoxy-2-butenoate (80mg, 0.35mmo1) in lml anhydrous dichloromethane was added. Reaction was stirred at room temperature overnight. Reaction was quenched with Sml 1N HCl after which an additional 20m1 dichloromethane was added.
Organic was washed with 2x20m1 water, dried over magnesium sulfate and concentrated to give (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)-4-methoxybut-2-enamide (150mg, 85%) as a white foam after drying which was sufficiently pure to be used without further purification.
To a solution of (2E)-N-[4-(2-{[(tent-butyl)amino]sulfonyl)phenyl)phenyl]-3-(3-cyanophenyl)-4-methoxybut-2-enamide (150mg, 0.298mmo1) in lOml 1:1 ethyl acetate:anhydrous methanol cooled to -78°C was bubbled HCl gas until saturation was achieved. Reaction was allowed to warm to room temperature and stirred overnight. The reaction was then concentrated in vacuo and dried under hi vacuum.
The dried methyl imidate residue was dissolved in Sml anhydrous methanol to which ammonium acetate (77mg, lmmol) was added and the reaction heated to reflux for 2 hours. The reaction was concentrated, treated with trifluoroacetic acid (lOml) for 2hrs, concentrated and purified on a 2x25cm Vydac C,g HPLC column to give 3-((lE)-1-(methoxymethyl)-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}vinyl)benzenecarboxamidine (34mg, (25%) as a fluffy off white powder after lyophilization. ES-MS (M+H+): 465.1 S
S Example 67:
u_N
H
N
H2fv nn To a solution of 3-((lE)-1-(methoxymethyl)-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}vinyl)-benzenecarboxamidine (Smg, O.Olmmol) in 4m1 methanol was added 10% Pd on carbon (lmg). Mixture was treated with hydrogen at 1 atmosphere under balloon for lhr. Reaction was filtered through a pad of Celite, concentrated and lyophilized to give 3-(1-(methoxymethyl)-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}-ethyl)benzenecarboxamidine (Smg, 100%) as a fluffy white powder. ES-MS (M+H'): 467.15 BIOLOGICAL ACTIVITY EXAMPLES
Evaluation of the compounds of this invention is guided by in vitro protease activity assays (see below) and in vivo studies to evaluate antithrombotic efficacy, and effects on hemostasis and hematological parameters.
The compounds of the present invention are dissolved in buffer to give solutions containing concentrations such that assay concentrations range from 0 to 100 ~M. In the assays for thrombin, prothrombinase and factor Xa, a synthetic chromogenic substrate is added to a solution containing test compound and the enzyme of interest and the residual catalytic activity of that enzyme is determined spectrophotometrically. The IC50 of a compound is determined from the substrate turnover. The IC50 is the concentration of test compound giving 50% inhibition of the substrate turnover. The compounds of the present invention desirably have an ICSO of less than 500 nM in the factor Xa assay, preferably less than 200 nM, and more preferred compounds have an IC50 of about 100 nM or less in the factor Xa assay. The compounds of the present invention desirably have an IC50 of less than 4.0 ~,M in the prothrombinase assay, preferably less than 200 nM, and more preferred compounds have an IC50 of about 10 nM or less in the prothrombinase assay. The compounds of the present invention desirably have an IC50 of greater than 1.0 uM in the thrombin assay, preferably greater than 10.0 ~.M, and more preferred compounds have an IC50 of greater than 100.0 pM in the thrombin assay.
Amidolytic Assays for determining_protease inhibition activity The factor Xa and thrombin assays are performed at room temperature, in 0.02 M Tris~HCl buffer, pH 7.5, containing 0.15 M NaCI. The rates of hydrolysis of the para-nitroanilide substrate S-2765 (Chromogenix) for factor Xa, and the substrate Chromozym TH (Boehringer Mannheim) for thrombin following preincubation of the enzyme with inhibitor for 5 minutes at room temperature, and were determined using the Softmax 96-well plate reader (Molecular Devices), monitored at 405 nm to measure the time dependent appearance of p-nitroaniline.
The prothrombinase inhibition assay is performed in a plasma free system with modifications to the method described by Sinha, U. et al., Thromb. Res., Z, 427-436 (1994). Specifically, the activity of the prothrombinase complex is determined by measuring the time course of thrombin generation using the p-nitroanilide substrate Chromozym TH. The assay consists of preincubation ( 5 minutes) of selected compounds to be tested as inhibitors with the complex formed from factor Xa (0.5 nM), factor Va (2 nM), phosphatidyl serine:phosphatidyl choline (25:75, 20 pM) in 20 mM Tris~HCl buffer, pH 7.5, containing 0.15 M NaCI, 5 mM
CaCl2 and 0.1% bovine serum albumin. Aliquots from the complex-inhibitor mixture are added to prothrombin ( 1 nM) and Chromozym TH (0.1 mM). The rate of substrate cleavage is monitored at 405 nm for two minutes. Eight different concentrations of inhibitor are assayed in duplicate. A standard curve of thrombin generation by an equivalent amount of untreated complex are used for determination of percent inhibition.
Antithrombotic Efficac~in a Rabbit Model of Venous Thrombosis A rabbit deep vein thrombosis model as described by Hollenbach, S. et al., Thromb. Haemost. 71, 357-362 (1994), is used to determine the in-vivo antithrombotic activity of the test compounds. Rabbits are anesthetized with LM. injections of Ketamine, Xylazine, and Acepromazine cocktail. A standardized protocol consists of insertion of a thrombogenic cotton thread and copper wire apparatus into the abdominal vena cava of the anesthetized rabbit. A non-occlusive thrombus is allowed to develop in the central venous circulation and inhibition of thrombus growth is used as a measure of the antithrombotic activity of the studied compounds. Test agents or control saline are administered through a marginal ear vein catheter. A femoral vein catheter is used for blood sampling prior to and during steady state infusion of test compound.
Initiation of thrombus formation begins immediately after advancement of the cotton thread apparatus into the central venous circulation. Test compounds are administered from time = 30 min to time = 150 min at which the experiment is terminated. The rabbits are euthanized and the thrombus excised by surgical dissection and characterized by weight and histology.
Blood samples are analyzed for changes in hematological and coagulation parameters.
Effects of Compounds in Rabbit Venous Thrombosis model Administration of compounds in the rabbit venous thrombosis model demonstrates antithrombotic efficacy at the higher doses evaluated. There are no significant effects of the compound on the aPTT and PT prolongation with the highest dose (100 ~g/kg + 2.57 ~g/kg/min). Compounds have no significant effects on hematological parameters as compared to saline controls. All measurements are an average of all samples after steady state administration of vehicle or (D)-Arg-Gly-Arg-thiazole. Values are expressed as mean + SD.
Without further description, it is believed that one of ordinary skill in the art can, using the preceding description and the following illustrative examples, make and utilize the compounds of the present invention and practice the claimed methods.
Prodrugs commonly known in the art include acid derivatives well known to practitioners of the art, such as, for example, esters prepared by reaction of the parent acids with a suitable alcohol, or amides prepared by reaction of the parent acid compound with an amine, or basic groups reacted to form an acylated base derivative. Moreover, the prodrug derivatives of this invention may be combined with other features herein taught to enhance bioavailability.
As mentioned above, the compounds of this invention find utility as therapeutic agents for disease states in mammals which have disorders of coagulation such as in the treatment or prevention of unstable angina, refractory angina, myocardial infarction, transient' ischemic attacks, thrombotic stroke, embolic stroke, disseminated intravascular coagulation including the treatment of septic shock, deep venous thrombosis in the prevention of pulmonary embolism or the treatment of reocclusion or restenosis of reperfizsed coronary arteries.
Further, these compounds are useful for the treatment or prophylaxis of those diseases which involve the production and/or action of factor Xa/prothrombinase complex. This includes a number of thrombotic and prothrombotic states in which the coagulation cascade is activated which include but are not limited to, deep venous thrombosis, pulmonary embolism, myocardial infarction, stroke, thromboembolic complications of surgery and peripheral arterial occlusion.
Accordingly, a method for preventing or treating a condition in a mammal characterized by undesired thrombosis comprises administering to the mammal a therapeutically effective amount of a compound of this invention. In addition to the disease states noted above, other diseases treatable or preventable by the administration of compounds of this invention include, without limitation, occlusive coronary thrombus formation resulting from either thrombolytic therapy or percutaneous transluminal coronary angioplasty, thrombus formation in the venous vasculature, disseminated intravascular coagulopathy, a condition wherein there is rapid consumption of coagulation factors and systemic coagulation which results in the formation of life-threatening thrombi occurring throughout the microvasculature leading to widespread organ failure, hemorrhagic stroke, renal dialysis, blood oxygenation, and cardiac catheterization.
The compounds of the invention also find utility in a method for inhibiting the coagulation biological samples, which comprises the administration of a compound of the invention.
The compounds of the present invention may also be used in combination with other therapeutic or diagnostic agents. In certain preferred embodiments, the compounds of this invention may be coadministered along with other compounds typically prescribed for these conditions according to generally accepted medical practice such as anticoagulant agents, thrombolytic agents, or other antithrombotics, including platelet aggregation inhibitors, tissue plasminogen activators, urokinase, prourokinase, streptokinase, heparin, aspirin, or warfarin. The compounds of the present invention may act in a synergistic fashion to prevent reocclusion following a successful thrombolytic therapy and/or reduce the time to reperfusion. These compounds may also allow for reduced doses of the thrombolytic agents to be used and therefore minimize potential hemorrhagic side-effects. The compounds of this invention can be utilized in vivo, ordinarily in mammals such as primates, (e.g.
humans), sheep, horses, cattle, pigs, dogs, cats, rats and mice, or in vitro.
The biological properties of the compounds of the present invention can be readily characterized by methods that are well known in the art, for example by the in vitro protease activity assays and in vivo studies to evaluate antithrombotic efficacy, and effects on hemostasis and hematological parameters, such as are illustrated in the examples.
Diagnostic applications of the compounds of this invention will typically utilize formulations in the form of solutions or suspensions. In the management of thrombotic disorders the compounds of this invention may be utilized in compositions such as tablets, capsules or elixirs for oral administration, suppositories, sterile solutions or suspensions or injectable administration, and the like, or incorporated into shaped articles. Subjects in need of treatment (typically mammalian) using the compounds of this invention can be administered dosages that will provide optimal efficacy. The dose and method of administration will vary from subject to subject and be dependent upon such factors as the type of mammal being treated, its sex, weight, diet, concurrent medication, overall clinical condition, the particular compounds employed, the specific use for which these compounds are employed, and other factors which those skilled in the medical arts will recognize.
Formulations of the compounds of this invention are prepared for storage or administration by mixing the compound having a desired degree of purity with physiologically acceptable carriers, excipients, stabilizers etc., and may be provided in sustained release or timed release formulations. Acceptable carriers or diluents for therapeutic use are well known in the pharmaceutical field, and are described, for example, in Remington's Pharmaceutical Sciences, Mack Publishing Co., (A.R.
Gennaro edit. 1985). Such materials are nontoxic to the recipients at the dosages and concentrations employed, and include buffers such as phosphate, citrate, acetate and other organic acid salts, antioxidants such as ascorbic acid, low molecular weight (less than about ten residues) peptides such as polyarginine, proteins, such as serum albumin, gelatin, or immunoglobulins, hydrophilic polymers such as polyvinylpyrrolidinone, amino acids such as glycine, glutamic acid, aspartic acid, or arginine, monosaccharides, disaccharides, and other carbohydrates including cellulose or its derivatives, glucose, mannose or dextrins, chelating agents such as EDTA, sugar alcohols such as mannitol or sorbitol, counterions such as sodium and/or nonionic surfactants such as Tween, Pluronics or polyethyleneglycol.
Dosage formulations of the compounds of this invention to be used for therapeutic administration must be sterile. Sterility is readily accomplished by filtration through sterile membranes such as 0.2 micron membranes, or by other conventional methods. Formulations typically will be stored in lyophilized form or as an aqueous solution. The pH of the preparations of this invention typically will be 3-11, more preferably 5-9 and most preferably 7-8. It will be understood that use of certain of the foregoing excipients, Garners, or stabilizers will result in the formation of cyclic polypeptide salts. While the preferred route of administration is by injection, other methods of administration are also anticipated such as orally, intravenously (bolus and/or infusion), subcutaneously, intramuscularly, colonically, rectally, nasally, transdermally or intraperitoneally, employing a variety of dosage forms such as suppositories, implanted pellets or small cylinders, aerosols, oral dosage formulations and topical formulations such as ointments, drops and dermal patches. The compounds of this invention are desirably incorporated into shaped articles such as implants which may employ inert materials such as biodegradable polymers or synthetic silicones, for example, Silastic, silicone rubber or other polymers commercially available.
The compounds of the invention may also be administered in the form of liposome delivery systems, such as small unilamellar vesicles, large unilamellar vesicles and multilamellar vesicles. Liposomes can be formed from a variety of lipids, such as cholesterol, stearylamine or phosphatidylcholines.
The compounds of this invention may also be delivered by the use of antibodies, antibody fragments, growth factors, hormones, or other targeting moieties, to which the compound molecules are coupled. The compounds of this invention may also be coupled with suitable polymers as targetable drug carriers.
Such polymers can include polyvinylpyrrolidinone, pyran copolymer, polyhydroxy-propyl-methacrylamide-phenol, polyhydroxyethyl-aspartamide-phenol, or polyethyleneoxide-polylysine substituted with palmitoyl residues. Furthermore, compounds of the invention may be coupled to a class of biodegradable polymers useful in achieving controlled release of a drug, for example polylactic acid, polyglycolic acid, copolymers of polylactic and polyglycolic acid, polyepsilon caprolactone, polyhydroxy butyric acid, polyorthoesters, polyacetals, polydihydropyrans, polycyanoacrylates and cross linked or amphipathic block copolymers of hydrogels. Polymers and semipermeable polymer matrices may be formed into shaped articles, such as valves, stems, tubing, prostheses and the like.
Therapeutic compound liquid formulations generally are placed into a container having a sterile access port, for example, an intravenous solution bag or vial having a stopper pierceable by hypodermic injection needle.
Therapeutically effective dosages may be determined by either in vitro or in vivo methods. For each particular compound of the present invention, individual determinations may be made to determine the optimal dosage required. The range of therapeutically effective dosages will be influenced by the route of administration, the therapeutic objectives and the condition of the patient. For injection by hypodermic needle, it may be assumed the dosage is delivered into the body's fluids.
For other routes of administration, the absorption efficiency must be individually determined for each compound by methods well known in pharmacology.
Accordingly, it may be necessary for the therapist to titer the dosage and modify the route of administration as required to obtain the optimal therapeutic effect.
The determination of effective dosage levels, that is, the dosage levels necessary to achieve the desired result, will be readily determined by one skilled in the art.
Typically, applications of compound are commenced at lower dosage levels, with dosage levels being increased until the desired effect is achieved.
The compounds of the invention can be administered orally or parenterally in an effective amount within the dosage range of about 0.,1 to 100 mg/kg, preferably about 0.5 to 50 mg/kg and more preferably about 1 to 20 mg/kg on a regimen in a single or 2 to 4 divided daily doses and/or continuous infusion.
Typically, about 5 to 500 mg of a compound or mixture of compounds of this invention, as the free acid or base form or as a pharmaceutically acceptable salt, is compounded with a physiologically acceptable vehicle, carrier, excipient, binder, preservative, stabilizer, dye, flavor etc., as called for by accepted pharmaceutical practice. The amount of active ingredient in these compositions is such that a suitable dosage in the range indicated is obtained.
Typical adjuvants which may be incorporated into tablets, capsules and the S like are binders such as acacia, corn starch or gelatin, and excipients such as microcrystalline cellulose, disintegrating agents like corn starch or alginic acid, lubricants such as magnesium stearate, sweetening agents such as sucrose or lactose, or flavoring agents. When a dosage form is a capsule, in addition to the above materials it may also contain liquid Garners such as water, saline, or a fatty oil.
Other materials of various types may be used as coatings or as modifiers of the physical form of the dosage unit. Sterile compositions for injection can be formulated according to conventional pharmaceutical practice. For example, dissolution or suspension of the active compound in a vehicle such as an oil or a synthetic fatty vehicle like ethyl oleate, or into a liposome may be desired.
Buffers, preservatives, antioxidants and the like can be incorporated according to accepted pharmaceutical practice.
Preparation of Compounds The compounds of the present invention may be synthesized by either solid or liquid phase methods described and referenced in standard textbooks, or by a combination of both methods. These methods are well known in the art. See, Bodanszky, "The Principles of Peptide Synthesis", Hafner, et al., Eds., Springer-Verlag, Berlin, 1984.
Starting materials used in any of these methods are commercially available from chemical vendors such as Aldrich, Sigma, Nova Biochemicals, Bachem Biosciences, and the like, or may be readily synthesized by known procedures.
Reactions are carried out in standard laboratory glassware and reaction vessels under reaction conditions of standard temperature and pressure, except where otherwise indicated.
During the synthesis of these compounds, the functional groups of the amino acid derivatives used in these methods are protected by blocking groups to prevent cross reaction during the coupling procedure. Examples of suitable blocking groups and their use are described in "The Peptides: Analysis, Synthesis, Biology", Academic Press, Vol. 3 (Gross, et al., Eds., 1981) and Vol. 9 (1987), the disclosures of which are incorporated herein by reference.
Non-limiting exemplary synthesis schemes are outlined directly below, and specific steps are described in the Examples. The reaction products are isolated and purified by conventional methods, typically by solvent extraction into a compatible solvent. The products may be further purified by column chromatography or other appropriate methods.
e1 CFg cHO J
+ ~F3C O,~ O~ KN(Me3Si)2 I ~C02CH3 O O 18-crown-6, THF
CN CN
i v ~ ~ NH2 O
S02NHtBu / ~ N ~ CN
H
AIMe3, DCM
S02NHtBu F
1.HCI, methanol O
2.NH40Ac, methanol, reflux / ~ N ~ I NH2 H NH
O
H2, 10%Pd/C, methanol / \ ~ ( NH2 / N
H NH
/ S02NHB~
\ I \ /
H
I/ \I CN
O
RX, Cs2C03 / SOzNHB~
\ I \ R /
I/ ~ \I
CN
O
1 ) HCI, MeOH
2) NH40Ac, MeOH
R
\ \ /
I / ~ \ I NHZ
O H
O ~ 50% TFA/DCN HO
CN CN
SO zNHtBu SO ZNHtBu / \ - - O I.NHzOH.HCI Et3N
\ / NHZ / \ \ / N \ 2.HOAc, AczO
/ 3.H2, 10% Pd/C
BOP, DIEA, DMF 4.TFA
CN
H O
/ \ \ / N
HN NHp O H N/~N \ / N \ O
HO I ~ ~ N~N~N
BOP, DIEA, DMF
CN CN
O
N ~ \ NON
HN -NHz 1~
a e4 ' O
O
Me0 ~ LiBH4 HO I ~ IBX, DM9D H
THF ~ ~ OMe ~ OMe OMe CN
CN CN
H N NHtBu 2 ~ O=S=O
Me0 (CF3CH20~P(O)CH2C02Me O ~ OMe KN(SiMe3)2, 18~xown-6 CN AIMe3, DCM
1. NCI, MeOH
O ~ OMe 2. NH40Ac, MeOH
S02NHt~ CN
C ~ OMe H2, 10% Pd/C
HN NH2 MeOH
O ~ OMe F O F
LDA, DMF H I ~ (CF3CHZO~P(O)CH2C02Me TI'~F ~ KN(SiMe3)2, 18-crown-6 CN CN
H2N NHtBu F I ~ O=S=O
Me0 ~i ~i O
CN AIMe3, DCM
F
1. HCI, MeOH
O ~ 2. NH40Ac, MeOH
S02NHtBu CN
F
H2, 10% Pd/C
O I i MeOH
S02NHt~
F
'~ O
S02NHt9~
S
Scheme 6 B(OH)2 (CF3S02)20 R~O~ ~ CN
O~ ~O DIEA / DCM CF3S02~0'~ ~O'( Pd(Ph3P)a K3POa / dioxane BuHtN~ ~O
S' _ O' _ H2N ~ / ~ ~ R ~ NH ~
O I ~ O S02NHtBu AIMe3, DCM ~ CN
CN
1. HCI, MeOH
2. NH40Ac, MeOH
NH
NH
H2, 10% Pd/C
MeOH
NH
NH
eme H3C ~ NBS, benzoyl peroxide Br I \ M3N=O H I
I ~ F CCI4 / F CHCI3 ~ F
CN CN CN
H N NHtBu O=S=O
(CF3CH20)2P(O)CHZCOzMe Me0 i I i KN(SiMe3)2, 18-crown-6 O F
CN AIMe3, DCM
\ / \ N I ~ 1. HCI, MeOH
_ _ i O ~F 2. NH40Ac, MeOH
SOZNHtBu CN
/ \ / \ N I ~ H2, 10% Pd/C
O
SOZNHZ F MeOH
HN NHZ
/ \ / \ N I ~
O ~ F
SOZNHz HN NHZ
Compositions and Formulations The compounds of this invention may be isolated as the free acid or base or converted to salts of various inorganic and organic acids and bases. Such salts are within the scope of this invention. Non-toxic and physiologically compatible salts are particularly useful although other less desirable salts may have use in the processes of isolation and purification.
A number of methods are useful for the preparation of the salts described above and are known to those skilled in the art. For example, reaction of the free acid or free base form of a compound of the structures recited above with one or more molar equivalents of the desired acid or base in a solvent or solvent mixture in S which the salt is insoluble, or in a solvent like water after which the solvent is removed by evaporation, distillation or freeze drying. Alternatively, the free acid or base form of the product may be passed over an ion exchange resin to form the desired salt or one salt form of the product may be converted to another using the same general process.
Diagnostic applications of the compounds of this invention will typically utilize formulations such as solution or suspension. In the management of thrombotic disorders the compounds of this invention may be utilized in compositions such as tablets, capsules or elixirs for oral administration, suppositories, sterile solutions or suspensions or injectable administration, and the like, or incorporated into shaped articles. Subjects in need of treatment (typically mammalian) using the compounds of this invention can be administered dosages that will provide optimal efficacy. The dose and method of administration will vary from subject to subject and be dependent upon such factors as the type of mammal being treated, its sex, weight, diet, concurrent medication, overall clinical condition, the particular compounds employed, the specific use for which these compounds are employed, and other factors which those skilled in,the medical arts will recognize.
Formulations of the compounds of this invention are prepared for storage or administration by mixing the compound having a desired degree of purity with physiologically acceptable Garners, excipients, stabilizers etc., and may be provided in sustained release or timed release formulations. Acceptable carriers or diluents for therapeutic use are well known in the pharmaceutical field, and are described, for example, in Remington's Pharmaceutical Sciences, Mack Publishing Co., (A.R.
Gennaro edit. 1985). Such materials are nontoxic to the recipients at the dosages and concentrations employed, and include buffers such as phosphate, citrate, acetate and other organic acid salts, antioxidants such as ascorbic acid, low molecular weight (less than about ten residues) peptides such as polyarginine, proteins, such as serum albumin, gelatin, or immunoglobulins, hydrophilic polymers such as polyvinalpyrrolidinone, amino acids such as glycine, glutamic acid, aspartic acid, or arginine, monosaccharides, disaccharides, and other carbohydrates including cellulose or its derivatives, glucose, mannose or dextrins, chelating agents such as EDTA, sugar alcohols such as mannitol or sorbitol, counterions such as sodium and/or nonionic surfactants such as Tween, Pluronics or polyethyleneglycol.
Dosage formulations of the compounds of this invention to be used for therapeutic administration must be sterile. Sterility is readily accomplished by filtration through sterile membranes such as 0.2 micron membranes, or by other conventional methods. Formulations typically will be stored in lyophilized form or as an aqueous solution. The pH of the preparations of this invention typically will be between 3 and 11, more preferably from 5 to 9 and most preferably from 7 to 8.
It will be understood that use of certain of the foregoing excipients, carriers, or stabilizers will result in the formation of cyclic polypeptide salts. While the preferred route of administration is by injection, other methods of administration are also anticipated such as intravenously (bolus and/or infusion), subcutaneously, intramuscularly, colonically, rectally, nasally or intraperitoneally, employing a variety of dosage forms such as suppositories, implanted pellets or small cylinders, aerosols, oral dosage formulations and topical formulations such as ointments, drops and dermal patches. The compounds of this invention are desirably incorporated into shaped articles such as implants which may employ inert materials such as biodegradable polymers or synthetic silicones, for example, Silastic, silicone rubber or other polymers commercially available.
° The compounds of this invention may also be administered in the form of liposome delivery systems, such as small unilamellar vesicles, large unilamellar vesicles and multilamellar vesicles. Liposomes can be formed from a variety of lipids, such as cholesterol, stearylamine or phosphatidylcholines.
The compounds of this invention may also be delivered by the use of antibodies, antibody fragments, growth factors, hormones, or other targeting moieties, to which the compound molecules are coupled. The compounds of this invention may also be coupled with suitable polymers as targetable drug Garners.
Such polymers can include polyvinylpyrrolidone, pyran copolymer, polyhydroxy-propyl-methacrylamide-phenol, polyhydroxyethyl-aspartamide-phenol, or polyethyleneoxide-polylysine substituted with palmitoyl residues. Furthermore, the factor Xa inhibitors of this invention may be coupled to a class of biodegradable polymers useful in achieving controlled release of a drug, for example polylactic acid, polyglycolic acid, copolymers of polylactic and polyglycolic acid, polyepsilon caprolactone, polyhydroxy butyric acid, polyorthoesters, polyacetals, polydihydropyrans, polycyanoacrylates and cross linked or amphipathic block copolymers of hydrogels. Polymers and semipermeable polymer matrices may be formed into shaped articles, such as valves, stems, tubing, prostheses and the like.
Therapeutic compound liquid formulations generally are placed into a container having a sterile access port, for example, an intravenous solution bag or vial having a stopper pierceable by hypodermic injection needle.
Therapeutically effective dosages may be determined by either in vitro or in vivo methods. For each particular compound of the present invention, individual determinations may be made to determine the optimal dosage required. The range of therapeutically effective dosages will naturally be influenced by the route of administration, the therapeutic objectives, and the condition of the patient.
For injection by hypodermic needle, it may be assumed the dosage is delivered into the body's fluids. For other routes of administration, the absorption efficiency must be individually determined for each inhibitor by methods well known in pharmacology.
Accordingly, it may be necessary for the therapist to titer the dosage and modify the route of administration as required to obtain the optimal therapeutic effect.
The determination of effective dosage levels, that is, the dosage levels necessary to achieve the desired result, will be within the ambit of one skilled in the art.
Typically, applications of compound are commenced at lower dosage levels, with dosage levels being increased until the desired effect is achieved.
A typical dosage might range from about 0.001 mg/kg to about 1000 mg/kg, preferably from about 0.01 mg/kg to about 100 mg/kg, and more preferably from about 0.10 mg/kg to about 20 mg/kg. Advantageously, the compounds of this invention may be administered several times daily, and other dosage regimens may also be useful.
Typically, about 0.5 to 500 mg of a compound or mixture of compounds of this invention, as the free acid or base form or as a pharmaceutically acceptable salt, is compounded with a physiologically acceptable vehicle, carrier, excipient, binder, preservative, stabilizer, dye, flavor etc., as called for by accepted pharmaceutical practice. The amount of active ingredient in these compositions is such that a suitable dosage in the range indicated is obtained.
Typical adjuvants which may be incorporated into tablets, capsules and the like are a binder such as acacia, corn starch or gelatin, and excipient such as microcrystalline cellulose, a disintegrating agent like corn starch or alginic acid, a lubricant such as magnesium stearate, a sweetening agent such as sucrose or lactose, or a flavoring agent. When a dosage form is a capsule, in addition to the above materials it may also contain a liquid Garner such as water, saline, a fatty oil. Other materials of various types may be used as coatings or as modifiers of the physical form of the dosage unit. Sterile compositions for injection can be formulated according to conventional pharmaceutical practice. For example, dissolution or suspension of the active compound in a vehicle such as an oil or a synthetic fatty vehicle like ethyl oleate, or into a liposome may be desired. Buffers, preservatives, antioxidants and the like can be incorporated according to accepted pharmaceutical practice.
In practicing the methods of this invention, the compounds of this invention may be used alone or in combination, or in combination with other therapeutic or diagnostic agents. 1n certain preferred embodiments, the compounds of this inventions may be coadministered along with other compounds typically prescribed for these conditions according to generally accepted medical practice, such as anticoagulant agents, thrombolytic agents, or other antithrombotics, including platelet aggregation inhibitors, tissue plasminogen activators, urokinase, prourokinase, streptokinase, heparin, aspirin, or warfarin. The compounds of this invention can be utilized in vivo, ordinarily in mammals such as primates, such as humans, sheep, horses, cattle, pigs, dogs, cats, rats and mice, or in vitro.
The preferred compounds of the present invention are characterized by their ability to inhibit thrombus formation with acceptable effects on classical measures of coagulation parameters, platelets and platelet function, and acceptable levels of bleeding complications associated with their use. Conditions characterized by undesired thrombosis would include those involving the arterial and venous vasculature.
With respect to the coronary arterial vasculature, abnormal thrombus formation characterizes the rupture of an established atherosclerotic plaque which is S the major cause of acute myocardial infarction and unstable angina, as well as also characterizing the occlusive coronary thrombus formation resulting from either thrombolytic therapy or percutaneous transluminal coronary angioplasty (PTCA).
With respect to the venous vasculature, abnormal thrombus formation characterizes the condition observed in patients undergoing major surgery in the lower extremities or the abdominal area who often suffer from thrombus formation in the venous vasculature resulting in reduced blood flow to the affected extremity and a predisposition to pulmonary embolism. Abnormal thrombus formation further characterizes disseminated intravascular coagulopathy commonly occurs within both vascular systems during septic shock, certain viral infections and cancer, a condition wherein there is rapid consumption of coagulation factors and systemic coagulation which results in the formation of life-threatening thrombi occurring throughout the microvasculature leading to widespread organ failure.
The compounds of this present invention, selected and used as disclosed herein, are believed to be useful for preventing or treating a condition characterized by undesired thrombosis, such as (a) the treatment or prevention of any thrombotically mediated acute coronary syndrome including myocardial infarction, unstable angina, refractory angina, occlusive coronary thrombus occurring post-thrombolytic therapy or post-coronary angioplasty, (b) the treatment or prevention of any thrombotically mediated cerebrovascular syndrome including embolic stroke, thrombotic stroke or transient ischemic attacks, (c) the treatment or prevention of any thrombotic syndrome occurring in the venous system including deep venous thrombosis or pulmonary embolus occurnng either spontaneously or in the setting of malignancy, surgery or trauma, (d) the treatment or prevention of any coagulopathy including disseminated intravascular coagulation (including the setting of septic S shock or other infection, surgery, pregnancy, trauma or malignancy and whether associated with multi-organ failure or not), thrombotic thrombocytopenic purpura, thromboangiitis obliterans, or thrombotic disease associated with heparin induced thrombocytopenia, (e) the treatment or prevention of thrombotic complications associated with extracorporeal circulation (e.g. renal dialysis, cardiopulmonary bypass or other oxygenation procedure, plasmapheresis), (f) the treatment or prevention of thrombotic complications associated with instrumentation (e.g.
cardiac or other intravascular catheterization, infra-aortic balloon pump, coronary stmt or cardiac valve), and (g) those involved with the fitting of prosthetic devices.
Anticoagulant therapy is also useful to prevent coagulation of stored whole blood and to prevent coagulation in other biological samples for testing or storage.
Thus the compounds of this invention can be added to or contacted with any medium containing or suspected to contain factor Xa and in which it is desired that blood coagulation be inhibited, e.g., when contacting the mammal's blood with material such as vascular grafts, stems, orthopedic prostheses, cardiac stems, valves and prostheses, extra corporeal circulation systems and the like.
Without further description, it is believed that one of ordinary skill in the art can, using the preceding description and the following illustrative examples, make and utilize the compounds of the present invention and practice the claimed methods. The following working examples therefore, specifically point out preferred embodiments of the present invention, and are not to be construed as limiting in any way the remainder of the disclosure.
EXAMPLES
H H
OMe I I
i O
CN
To a solution of bis(2,2,2-trifluoroethyl)(methoxylcarbonylmethyl)phosphate (0.665m1, 3.14mmo1) and 18-crown-6 (4.14g, 15.7mmo1) in tetrahydrofuran (SOmI) at -78 °C was added potassium bis(trimethylsilyl)amide (6.3m1, 3.15mmo1) dropwise. After the addition was complete, 3-cyanobenzaldehyde (0.412g, 3.14mmo1) in tetrahydrofuran (lOml) was added at -78 °C. The mixture was stirred at -78 °C for additional 1 hr. Saturated ammonia chloride solution was added to quench the reaction. Ether and water were added. The organic layer was separated, and the aqueous layer was extracted with ether once more. The combined organic extracts were dried over magnesium sulfate and concentrated in vacuo. The crude residue was purified by silica gel column chromatography using solvent system 10% ethyl acetate in hexane as eluent to give the title compound as a white solid (1.12g, 100%).
ES-MS (M+H)+ = 188.
xam 1e 2 / \
SOzNHtBu To a solution of tert-butylamine (5.73g, 78.4mmo1) and triethylamine (16.6m1, 1 l9mmol) in dichloromethane (200m1) in an ice bath was added benzenesulfonyl chloride (13.85g, 78.4mmo1) dropwise. The mixture was stirred at room temperature overnight. It was washed with saturated sodium carbonate (60m1) and brine (60m1). The organic layer was separated, and the aqueous layer was extracted with dichloromethane (2x50m1). The combined organic extracts were dried over magnesium sulfate. The solvent was evaporated in. vacuo to give the title compound as a light yellowish solid (15.92g, 95%). ES-MS (M+H)+ = 214.
Example 3 B~oHy~
S02NHtBu To a solution of the compound of example 2 (15.92g, 74.7mmo1) in tetrahydrofuran (200m1) in an ice bath was added 1.6M n-butyllithium in hexane (100m1, 164mmol) dropwise over 30 minutes. The mixture remained a clear solution. In an ice bath it was added triisopropylborate (24.1m1, 104mmo1) dropwise. The mixture was stirred at room temperature for 3.Shrs, solution becoming cloudy. After it was cooled in an ice bath, 1N hydrochloride (200m1) was added. The mixture was stirred at room temperature overnight. It was extracted with ether (2x50m1). The organic extract was washed with 1N sodium hydroxide (2x60m1). The aqueous solution was acidified to pH=1 with 6N hydrochloride, and then extracted with ether (2x100m1).
The ether extract was dried over magnesium sulfate, and concentrated in vacuo to give the title compound as a while solid (ll.Sg, 60%). ES-MS (M+H)+ = 258.
Ex 4 S02NHtBu F
To a solution of the compound of example 3 (2.06g, 8mmo1) in toluene (60m1) was added water (4m1), 8N sodium hydroxide (8m1), isopropanol (16m1), 2-fluoro-4-iodoaniline (3.8g, l6mmol) and tetrakis(triphenylphosphine)palladium(0) (464mg, 0.4mmo1). The mixture was refluxed for 3-4 hrs, cooled to room temperature, and diluted with ethyl acetate. The organic layer was washed with water (25m1), and dried over magnesium sulfate. After the evaporation of the solvent in vacuo, the crude reside was purified by silica gel column chromatography using solvent system 20-30% ethyl acetate in hexane as eluent to give the title compound as a white solid (1.49g, 58%). ES-MS (M+H)+=323.
Ex a ~I
CN
S02NHtBu F
S To a solution of compound of example 4 (161mg, O.Smmol) in dichloromethane (5m1) was added 2.0M trimethylaluminum in hexane (0.75m1, l.Smmo1). The mixture was stirred at room temperature for 30 minutes, methane gas evolved. A
solution of the compound of example 1 (94mg, O.Smmol) in dichloromethane (1m1) was added. The mixture was stirred at room temperature overnight. 1N
hydrochloride was added to acidify the solution to pH=2. After the addition of water and dichloromethane, the organic layer was separated, and the aqueous layer was extracted with dichloromethane. The combined organic extracts were dried over magnesium sulfate, and concentrated in vacuo to give the title compound as a yellow oil (260mg, 100%). ES-MS (M+H)+ = 478.
Example 6 / ~ ~ I NHz N
H NH
To a solution of the compound of example 5 (100mg, 0.21mmo1) in absolute methanol (3m1) in an ice bath was saturated with hydrochloride gas for 10 minutes.
The mixture was stirred at room temperature for 3 hrs. After the evaporation of solvent in vacuo, the residue was dissolved in absolute methanol (3m1), and ammonia acetate (97mg, 1.26mmo1) was added. The mixture was refluxed for 3 hrs.
The solvent was evaporated in vacuo. The crude residue was purified by RP-HPLC
to give the title compound as a white powder (53mg, 58%). ES-MS (M+H)+ = 439.
Example 7 N ~ I NH2 H NH
To a solution of the compound of example 6 (30mg, 0.07mmo1) in absolute methanol (2m1) was added 10% Pd/C (catalytic amount). The mixture was hydrogenated under balloon for lhr. After the filtration through Celite, the solvent was evaporated in vacuo. The residue was purified by RP-HPLC to give the compound as a white powder (25mg, 81 %). ES-MS (M+H)+ = 441.
Example 8 S02NHtBu CI
1 S To a solution of the compound of example 3 (2.06g, 8mmol) in toluene (60m1) was added water (4m1), 8N sodium hydroxide (8m1), isopropanol (16m1), 2-chloro-4-iodoaniline (4.06g, l6mmol) and tetrakis(triphenylphosphine)palladium(0) (464mg, 0.4mmo1). The mixture was refluxed for 3-4 hrs, cooled to room temperature, and diluted with ethyl acetate. The organic layer was washed with water (25m1), and dried over magnesium sulfate. After the evaporation of the solvent in vacuo, the crude reside was purified by silica gel column chromatography using solvent system 20-30% ethyl acetate in hexane as eluent to give the title compound as a white solid (1.43g, 53%). ES-MS (M+H)+= 339.
am 1 ~I
~ ~ / H ~ CN
S02NHtBu CI
To a solution of the compound of example 8 (100mg, 0.3mmo1) in dichloromethane (5m1) was added 2.0M trimethylaluminum in hexane (0.45m1, 0.9mmo1). The mixture was stirred at room temperature for 30 minutes, methane gas evolved. A
solution of the compound of example 1 (SSmg, 0.3mmo1) in dichlodomethane (1m1) was added. The mixture was stirred at room temperature overnight. 1N
hydrochloride was added to acidify the solution to pH=2. After the addition of water and dichloromethane, the organic layer was separated, and the aqueous layer was extracted with dichloromethane. The combined organic extracts were dried over magnesium sulfate, and concentrated in vacuo to give the title compound as a greenish solid (1 l Omg, 70%). ES-MS (M+H)+ = 494.
Example 10 ~ ~ I NH2 N
H NH
To a solution of the compound of example 9 (100mg, 0.2mmol) in absolute methanol (3m1) in an ice bath was saturated with hydrochloride gas for 10 minutes.
The mixture was stirred at room temperature for 3 hrs. After the evaporation of the solvent in vacuo, the residue was dissolved in absolute methanol (3m1), and ammonia acetate (92mg, l.2mmo1) was added. The mixture was refluxed for 3 hrs.
The solvent was evaporated in vacuo. The crude residue was purified by RP-HPLC
to give the title compound as a white powder (46mg, 51 %).
ES-MS (M+H)+ = 456.
Example 11 Production of 3-[(2-2-furyl)-5-oxo-1,3-oxazolin-4-ylidene)methyl]
benzenecarbonitrile.
N ~I
~O
//O
CN
A mixture of 3-cyanobenzaldehyde (2.102g, 15.320mmo1), N-2-furoylglycine (1.846g, 10.914mmo1), and sodium acetate (0.636g, 7.753mmo1) in 15m1 acetic anhydride was refluxed for 7 hours. The mixture was then cooled to room temperature before cooling in the freezer over night. The solid was washed with ice cold water then filtered (0.472g, 1.788mmo1, 16%). ES-MS(M+H)+=265.
F~xa_mple 1 Production of (2E)-N-[4(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)-2-(2-furylcarbonylamino)prop-2-enamide To a solution of {[2-(4-aminophenyl)phenyl]sulfonyl}(tert-butyl)amine (0.152g, O.SOOmmol) in 9m1 DCM was added trimethylaluminum (1m1, 2M solution in hexanes, 2mmo1) which was allowed to stir for'/2 hour. Then 3-[(2-(2-furyl)-5-oxo-1,3-oxazolin-4-ylidene)methyl]benzenecarbonitrile (0.11g, 0.417mmo1) was added drop wise as a solution in 3m1 DCM. Three hours later 6M HCl was added drop wise to pH=0. l Oml portions of water and DCM were also added and the aqueous layer was extracted twice with l Oml portions of DCM. The organic layers were dried over MgS04, filtered and concentrated in vaccu to yield the desired product (0.259, 0.456, 109%). ES-MS(M+H)+=569.
Example 13 Production of 3-(2-{N-[4-(2-{[(tert-butyl) amino] sulfonyl } phenyl)phenyl] carbamoyl } -2-(2-furylcarbonylamino)ethyl)benzenecarboxamidine To a solution of (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)-2-(2-furylcarbonylamino)prop-2-enamide (0.259g, 0.456mmo1) in 7m1 ethanol was added hydroxyamine (0.192g, 2.763mmo1) and triethyl amine (0.762m1, 5.407mmo1). This mixture was refluxed for 2 hours before it was concentrated in vaccu. The residue was dissolved in AcOH (5m1), then acetic anhydride (0.30m1, 3.182mmo1) was added and the mixture was allowed to stir forl.5 hours. The mixture was concentrated in vaccu. The residue was dissolved in dry MeOH
(3m1), 5%Pd/C (22.7m8) was added. A balloon filled with hydrogen gas was fitted to the flask with an adapter. The flask was evacuated and backfilled with hydrogen gas three times before being run for 0.75 hour. The mixture was then filtered over a bed of celite and concentrated in vaccu. The residue was purified via Preparative HPLC
to yield the desired product (0.0758, 0.128mmo1, 28%). ES-MS(M+H)+=588.
Example 14 Production of 3-(2-(2-furylcarbonylamino)-2-{N-[4-(2-sulfamoylphenyl)phenyl]-carbamoyl } ethyl)benzenecarboxamidine 3-(2- {N-[4-(2- { [(tert-butyl)amino] sulfonyl } phenyl)phenyl] carbamoyl } -2-(2-fiuyl-carbonylamino)ethyl)benzenecarboxamidine (0.0758, 0.128mmo1) was dissolved with TFA (6m1) for 2hours. The mixture was concentrated in vaccu and the residue was purified via Preparative HPLC, (0.0408, 0.075mmo1, 58%). ES-MS(M+H)+=532.
Exam 1p a 15 Production of (tert-butyl)(phenylsulfonyl)amine o~
S~o / \
To a solution of benzenesulfonyl chloride (30.008, 169.86mmol) in 100m1 DCM, in an ice bath, was added butyl amine (18m1, 171.28mmo1), then triethylamine(35m1, 251.1 lmmol), drop wise via addition funnel. This was allowed to warm to room temperature over 3hr. The mixture was then filtered and the filtrate was concentrated in vaccu. The pale yellow solid (35.03g, 164.46mmo1, 97%) was then rinsed with minimal amounts of DCM. ES-MS (M+Na)+=236.
S
Example 16 Production of (tert-butyl)(phenylsulfonyl)amine H
p B-OH
,_ To (tent-butyl)(phenylsulfonyl)amine (17.43g, 81.83mmo1) in 180m1 dry THF in an ice bath was added nBuLi (66m1, 2.5M in hexanes) via addition funnel. Then triisopropyl borate (33m1, 143.06mmo1) was added via addition funnel. The mixture was warmed to room temperature and allowed to stir for 4hr. The reaction mixture was then cooled in an ice bath before HCL (82m1, 3M) was added drop wise. This was allowed to stir at room temperature for 3hr. The mixture was then put in the freezer over the weekend. The reaction was then warmed to room temperature and extracted with ether. The aqueous layers were washed twice more with ether.
The combined organic layers were washed three times with SM NaOH aqueous solution.
The combined basic layers were acidified to pH=1 with 6M HCL solution. These acidified layers were then extracted three times with ether. These ether layers were then dried over MgS04, f ltered, then concentrated in vaccu to about SOmI
solution.
To this solution was added hexanes and a minimal amount of ethyl acetate. A
white precipitate is observed and the mixture in stored in the freezer to allow for crystallization. The white solid is then filtered and collected (14.65g, 57mm1, 70%) ES-MS (M+H)+=25 8.
Production of {[2-(4-aminophenyl)phenyl]sulfonyl}(tert-butyl)amine HyN
NH
~O
To a solution of 2-[(tert-butyl amino)sulfonyl] phenyl boronic acid (6.00g, 23.35mmo1) in 120m1 toluene was added water (16m1), isopropanol (60m1), and NaOH (40m1, SM aqueous solution). To this were added 4-bromoaniline and Pd(Ph3P)4. This heterogeneous mixture is then refluxed for 6hr, then stirred at room temperature over night before refluxing for another l.Shr. The reaction mixture is then extracted with water and ethyl acetate. The aqueous layer is extracted twice with ethyl acetate. The organic layers are then dried over MgS04, filtered and concentrated in vaccu. The crude residue is purified by silica gel flash chromatography. The desired product can be eluded with 30% ethyl acetate in hexanes and concentrated to an orange solid (5.06g, 16.65, 71 %). ES-MS(M+H)+=305.
Example 18 O
H ~NH2 Step (a):
To a 0°C solution of 4-((2-N-t-butylamonisulfonyl)phenyl) aniline (74.1 mg, 0.3 mmol, 1.0 equiv) in 5 mL of CHZC12 was added a solution of AlMe3 (2M in hexanes, 0.7 mL, 5 equiv). After l5min, methyl 2-(3-cyanophenyl)acrylate (56.1 mg, 1.0 equiv) was added. The resulting solution was stirred overnight, carefully quenched with water, diluted with ethyl acetate. The organic layer was dried, evaporated and chromatographied on silica gel to give the product in 55% yield. LRMS found for C23H19N2~3'~ (M+H)+: 403.1.
Step (b):
The compound obtained in step (a) (25 mg) was dissolved in S mL of methanol .
The reaction mixture was cooled to 0°C and HCl gas was bubbled in until saturation. The mixture was stirred at rt overnight. The solvent was evaporated and the resulting residue was treated with ammonium acetate and 10 ml methanol at reflux temperature for 2 h. The solvent was removed at reduced pressure and the crude benzamidine was purified by HPLC (C18 reversed phase) eluting with 0.5% TFA in H20/CH3CN to give the desired salt in 77% yield. LRMS found for CZgH22N3~3'S
(M+H)+: 420.1.
Step (c):
The compound obtained in step (b) (8 mg) and S mg of 10% Pd/C was suspended in 1 mL of methanol . The reaction mixture was stirred under 1 atm hydrogen balloon for 2h and filtered. The solvent was removed at reduced pressure and the crude benzamidine was purified by HPLC (C18 reversed phase) eluting with 0.5% TFA in H20/CH3CN to give the desired salt in 63% yield. LRMS found for C23H24N3~3S
(M+H)+: 422.1.
Example 19 F
CN
2-Fluoro-5-methyl benzonitrile (1.26g, 9.32 mmol) was mixed with NBS (1.66 g, 9.32 mmol), benzoyl peroxide (79 mg, 0.33 mmol) in CC14 (45mL). The mixture was refluxed for 2.5 hrs. It was cooled to room temperature, filtered and concentrated in vacuo to give the title compound. ES-MS (M+H)+ = 213.1.
Example 20 O
F
CN
To a solution of compound of example 19 (9.32 mmol) in CHC13 (50 mL), was added trimethylamino N-oxide (1.7 g, 23.3 mmol). The mixture was refluxed for hrs. Water was added. The organic layer was dried over MgS04, filtered and filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography using solvent system 20% EtOAc in hexane as eluant to give the title compound. ES-MS (M+H)+ = 150.1.
Exam In a 21 Me0 O
F
CN
To a solution of bis(2,2,2-trifluoroethyl)(methoxycarbonylmethyl) phosphonate (0.12 mL, 0.58 mmol) and 18-crown-6 (770 mg, 2.92 mmol) in THF (5 mL) at -78°C, was added potassium bis(trimethylsilyl)amide (1.17 mL, 0.57 mmol) dropwise. After the addition was complete, compound of example 2 (87 mg, 0.58 mmol) in THF (2 mL) was added. The mixture was stirred at -78°C for 1 hour.
Aqueous NH4Cl solution was added to quench the reaction. Water and EtOAc was added to the mixture. The organic layer was dried over MgS04, filtered and concentrated in vacuo. This was purified by silica gel column chromatography using solvent system 20% EtOAc in hexane as eluant to give the title compound (85 mg, 71 %). ES-MS (M+H)+ = 206.1.
exam In a 22 S02NHtBu H2N \ / \ /
To a solution of compound of example 3 (6.4 g, 25 mmol) in toluene (120 mL) was added water (15 mL), SN NaOH solution (38.5 mL), isopropanol (60 mL) 4-bromoaniline and tetrakis(triphenylphosphine)palladium(0). The mixture was refluxed for six hours, cooled to room temperature, diluted with EtOAc. The organic layer was washed with water, dried with MgS04, filtered and concentrated.
This was purified by silica gel column chromatography using solvent system 30%
EtOAc in hexane as eluant to give the title compound (5g, 66%). ES-MS (M+H)+ _ 305.1.
Example 23 / \ / \ N
O ~ F
S02NHtBu CN
To a solution of compound of example 22 (121.6 mg, 0.4 mmol) in DCM (3 mL) was added trimethylaluminum (0.6 mL, 2M in hexane) dropwise. The reaction mixture was stirred at room temperature for 30 min. Compound of example 21 (82 mg, 0.4 mmol) in DCM (2 mL) was added dropwise. The mixture was stirred at room temperature overnight. 2N HCl was added to pH 2. Water and DCM were added. The organic layer was dried over MgS04 and concentrated in vacuo. It was purified by silica gel column chromatography using solvent system 50% EtOAc in hexane as eluant to give the title compound. ES-MS (M+Na)+ = 500.1.
Example 24 / \ / \
O / F
A solution of the compound of example 23 (99 mg, 0.208 mmol) in MeOH (10 mL) was treated with a stream of HCl gas for 10 min. at 0°C. The resulting solution was capped, stirred at room temperature overnight and evaporated in vacuo. The residue was reconstituted in MeOH (10 mL) and the mixture was treated with NH40Ac (80 mg, 1.04 mmol). The reaction mixture was refluxed for 2 hrs. and concentrated in vacuo. The obtained residue was purified by RP-HPLC to give the title compound as a white powder. ES-MS (M+H)+ = 439.1.
Exam In a 25 / \ / \
O / F
The compound of example 24 (10 mg, 0.022 mmol) was dissolved in MeOH (5 mL) and 10% Pd/C (catalytic amount) was added. The mixture was hydrogenated under balloon overnight, filtered through Celite to remove the catalyst and the filtrate was evaporated. The obtained residue was purified by RP-HPLC to give the title compound as a white powder. ES-MS (M+H)+ = 441.1.
Exam In a 26 O F
H
CN
To a solution of LDA (2.6 mL, 2N solution in hexane, 5.2 mmol) in THF (10 mL) at -78°C, was added 4-fluorobenzonitrile in THF (10 mL) dropwise. The mixture was stirred at -78°C for 1 hour. To this was added DMF (0.4 mL, 0.55 mmol).
The mixture was stirred at -78°C for another 15 min., quenched rapidly with AcOH (2 mL) and water (10 mL), extracted with ether (SO mL). The ether extracts were washed with 1N HCl (10 mL), brine (10 mL), dried over MgS04, filtered and concentrated in vacuo to give the title compound. (M+H)+ = 150.
Example 27 F
Me0 O
CN
To a solution of bis(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate (0.875 mL, 4.14 mmol) and 18-crown-6 (5.46 g, 20.7 mmol) in THF (20 mL) at -78°C, was added potassium bis(trimethylsilyl)amide (8.3 mL, 4.15 mmol) dropwise.
After the addition was complete, compound of example 26 (616 mg, 4.14 mmol) in THF (10 mL) was added. The mixture was stirred at -78°C for 1 hour.
Aqueous NH4C1 solution was added to quench the reaction. Water and EtOAc was added to the mixture. The organic layer was dried over MgS04, filtered and concentrated in vacuo. This was purified by silica gel column chromatography using solvent system 20% EtOAc in hexane as eluant to give the title compound (375 mg, 44%). ES-MS
(M+H)+ = 206.1.
Example 28 F
'-' O
S02NHtBu CN
To a solution of compound of example 22 (553 mg, 1.82 mmol) in DCM (9 mL) was added trimethylaluminum (2.73 mL, 2M in hexane, 5.46 mmol) dropwise. The reaction mixture was stirred at room temperature for 1 hour. Compound of example 27 (373 mg, 1.82 mmol) in DCM (5 mL) was added dropwise. The mixture was stirred at room temperature overnight. 2N HCl was added to pH 2. Water and DCM
were added. The organic layer was dried over MgS04 and concentrated in vacuo.
It was purified by silica gel column chromatography using solvent system 50%
EtOAc in hexane as eluant to give the title compound (283 mg). ES-MS (M+Na)+ =
500.1.
Example 29 F
O
S02NHtBu A solution of the compound of example 28 (283 mg, 0.593 mmol) in MeOH (10 mL) was treated with a stream of HCl gas for 10 min. at 0°C. The resulting solution was capped, stirred at room temperature overnight and evaporated in vacuo. The residue was reconstituted in MeOH (10 mL) and the mixture was treated with NH40Ac (228 mg, 2.97 mmol). The reaction mixture was refluxed for 2 hrs. and concentrated in vacuo. The obtained residue was purified by RP-HPLC to give the title compound as a white powder. ES-MS (M+H)+ = 439.1.
Example 30 F
O
S02NHtBu Compound of example 29 (12 mg, 0.027 mmol) was dissolved in MeOH (5 mL) and 10% PdIC (catalytic amount) was added. The mixture was hydrogenated under balloon. overnight, filtered through Celite to remove the catalyst and the filtrate was evaporated. The obtained residue was purified by RP-HPLC to give the title compound as a white powder. ES-MS (M+H)+ = 441.1.
Example 31 Ho OMe CN
To a solution of methyl-3-cyano-4-methoxybenzoate (5g, 26.2 mmol) in THF (50 mL) was added lithium borohydride (53 mL, 2.00M solution in THF, 105 mmol) at room temperature. The mixture was stirred at room temperature overnight. IN
HCl was slowly added until bubbling stopped. THF was removed in vacuo and EtOAc and water were added. The organic layer was washed with water, saturated NaHC03 solution, brine, dried with NazS04 and solvent evaporated in vacuo to give the title compound (3.7 g, 86.7%).
Example 32 O
OMe CN
To a solution of compound of example 31 (2g, 12.3 mmol) in DMSO (50 mL) was added IBX (4.673g, 17.7 mmol) slowly. The mixture was stirred at room temperature overnight. EtOAc and water were added. The formed precipitate was removed. The organic layer was washed with 1N HCI, water, saturated NaHC03, brine, dried over NazS04 and concentrated in vacuo. The obtained residue was purified by silica gel column chromatography using DCM as eluant to give the title compound (1.1g, 56%). ES-MS (M+H)+= 162.1.
Example 33 Me0 O I/
home CN
To a solution of bis(2,2,2-trifluoroethyl)(methoxycarbonylmethyl) phosphonate (1.39 mL, 6.57 mmol) in THF (130 mL) at -78°C was added 18-crown-6 (8.6, 33.9 mmol), potassium bis(trimethylsilyl)amide (14.4 mL, 7.22 mmol) dropwise. The mixture was stirred at at -78°C for 30 min. Compound of example 32 (1.06 g, 6.57 mmol) was then added. The mixture was warmed to room temperature and stirred for 1 hour. Aqueous NH4C1 solution was added to quench the reaction.
Water and EtOAc was added to the mixture. The organic layer was dried over MgS04, filtered and concentrated in vacuo to give the title compound (1.175g, 87%).
ES-MS (M+H)+ = 218.1.
Exam lie 34 / \ / \ N I w O home S02NHtBu CN
To a solution of compound of example 22 (457 mg, 1.5 mmol) in DCM (4 mL) was added trimethylaluminum (0.9 mL, 2M in hexane, 1.8 mmol) dropwise. The reaction mixture was stirred at room temperature for 1 hour. Compound of example 33 (326 mg, 1.5 mmol) in DCM (5 mL) was added dropwise. The mixture was heated to reflux briefly. 1N HCl was added to pH 2. Water and DCM were added.
The organic layer was washed with brine, dried over MgS04 and concentrated in vacuo. It was purified by silica gel column chromatography using solvent system 30-50% EtOAc in hexane as eluant to give the title compound (450 mg, 61.3%).
ES-MS (M+H)+ = 490.1.
Example 35 / \ / \
O ~ OMe S02NHz A solution of the compound of example 34 (200 mg, 0.408 mmol) in MeOH (10 mL) was treated with a stream of HCl gas for 10 min. at 0°C. The resulting solution was capped, stirred at room temperature overnight and evaporated in vacuo. The residue was reconstituted in MeOH (10 mL) and the mixture was treated with NH40Ac (650 mg, 8.16 mmol). The reaction mixture was refluxed for 2 hrs. and concentrated in vacuo. The obtained residue was purified by RP-HPLC to give the title compound as a white powder. ES-MS (M+H)+ = 451.1.
Example 36 / \ / \
O ~ OMe Compound of example 35 (6 mg, 0.027 mmol) was dissolved in MeOH (2 mL) and 10% Pd/C (catalytic amount) was added. The mixture was hydrogenated under balloon overnight, filtered through Celite to remove the catalyst and the filtrate was evaporated to give the title compound as a white powder. ES-MS (M+H)+ = 443.1.
Example37 H NHBoc \ / \
'~ O i S02NHtBu CN
Boc-m-CN-Phenylalanine -OH (200 mg, 0.69 mmol) and compound of example 22 (210 mg, 0.69 mmol) were dissolved in DMF (3 mL). DIEA (0.24 mL, 1.4 mmol) was added followed by the addition of the coupling reagent PyBOP (572 mg, 1.1 mmol). The solution was stirred at room temperature for 12 hours. The reaction mixture was diluted in a mixture of EtOAc/HzO. The organic layer was washed with water, saturated NazC03, water, 1M KHS04, brine, dried over MgS04, filtered and solvent evaporated to give the title compound. ES-MS (M+H)+ = 521.1.
Example 38 / \ /
O
A solution of the compound of example 37 (132 mg, 0.23 mmol) in MeOH (10 mL) was treated with a stream of HCl gas for 10 min. at 0°C. The resulting solution was capped, stirred at room temperature overnight and evaporated in vacuo. The residue was reconstituted in MeOH (10 mL) and the mixture was treated with NH40Ac (540 mg, 7 mmol). The reaction mixture was refluxed for 2 hrs. and concentrated in vacuo. The obtained residue was purified by RP-HPLC to give the title compound as a white powder. ES-MS (M+H)+ = 438.1.
Example 39:
Tf0 C02Et To a solution of ethyl 2-oxocyclopentane carboxylate (1.56g, lOmmol) in 20m1 anhydrous dichloromethane was added triethylamine (1.06g, 10.5mmo1). Reaction was cooled under argon to -78°C to which trifluoro-methanesulfonic anhydride (2.96g, 10.5mmo1) was added dropwise via syringe over S minutes. Reaction was allowed to warm to room temperature and stirred over night. Next morning the reaction was diluted with 25m1 dichloromethane, organic was washed with 2xSOm1 water, 2xSOml 1N HCI, dried over magnesium sulfate, filtered and concentrated to give ethyl 2- f [(trifluoromethyl)sulfonyl]oxy}-1-cyclopentene-1-carboxylate (2.8g, 97%) as a light brown oil after drying. H'NMR (CDC13) : 1.27 -1.56 (t, 3H);
1.97-2.01 (m, 2H); 2.6-2.74 (m, 4H); 4.21-4.26 (m, 2H).
Example 40:
CN
To a solution of ethyl 2-{[(trifluoromethyl)sulfonyl]oxy}-1-cyclopentene-1-carboxylate (1.2g, 4.16mmol) in lOml anhydrous dioxane was added potassium phosphate (1.32g, 6.2mmol), 3-cyanophenyl boronic acid (0.612g, 4.16mmo1), and tetrakis (triphenylphosphine)palladium(0) (0.12g, O.lOmmol). Reaction mixture was heated to reflux and stirred overnight. Mixture was filtered through a pad of Celite, diluted with 50m1 ethyl acetate, washed with 2x50m1 water, 2x50m1 saturated brine solution, dried over magnesium sulfate, filtered and concentrated in vacuo.
Residue was chromatographed on silica gel using 5% EtOAc in hexane as the eluent to give ethyl 2-(3-cyanophenyl)-1-cyclopentene-1-carboxylate (0.7g, 71%) as a light yellow oil after drying. ES-MS (M+H+): 242.15. H'NMR (CDC13) : 1.09-1.13 (t, 3H);
1.96-2.01 (m, 2H); 2.80-2.84 (m, 4H); 7.39-7.59 (m, 4H).
Example 41:
HzN O
O=S~
H
N
H2N rvn To a solution of 2'-tert-butylaminosulfonyl-4-amino-[1,1']-biphenyl (60mg, 0.197mmo1) in 4m1 anhydrous dichloromethane was added a solution of 2M
trimethylaluminum in hexane (0.3m1, 0.59mmo1). Reaction was stirred at room temperature for 20 minutes to which a solution of ethyl 2-(3-cyanophenyl)-1-cyclopentene-1-carboxylate (48mg, 0.197mmol) in lml anhydrous dichloromethane.
Reaction was stirred at room temperature overnight. Reaction was quenched with 15m1 1N HCl after which an additional lOml dichloromethane was added. Organic was washed with 2x20m1 water, dried over magnesium sulfate and concentrated to give N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl][2-(3-cyanophenyl)cyclopent-1-enyl]carboxamide (80mg, 80%) as a white powder which was sufficiently pure to be used without further purification.
To a solution ofN-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl][2-(3-cyanophenyl)cyclopent-1-enyl]carboxamide (70mg, 0.137mmo1) in 5m1 anhydrous methanol cooled in an ice bath was bubbled HCl gas until saturation was achieved.
Reaction was allowed to warm to room temperature and stirred overnight. The reaction was then concentrated in vacuo and dried under hi vacuum. The dried residue was dissolved in 5m1 anhydrous methanol to which ammonium acetate (77mg, lmmol) was added and the reaction heated to reflux for 2 hours. The reaction was concentrated and purified on a 2x25cm Vydac C,g HPLC column to give 3-(2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}cyclopent-1-enyl)benzenecarboxamidine (40mg, 63%) as a fluffy white powder after lyophilization. ES-MS (M+H+): 461.15 S
Example 42:
HZN O
O=S~
H
N
H2N rvn To a solution of the 3-(2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}cyclopent-enyl)benzenecarboxamidine (7mg, O.Ol5mmol) in 4m1 methanol was added 10% Pd on carbon (l.Smg). Mixture was treated with SOpsi hydrogen on the PARK
apparatus for lhr. Reaction was filtered through a pad of Celite, concentrated and lyophilized to give the 3-(2-{N-[4-(2-sulfamoylphenyl)phenyl]-carbamoyl}cyclopentyl)benzenecarboxamidine (Smg, 71%) as a fluffy white powder. ES-MS (M+H+): 463.15 Example 43:
C02Et Tf0 C02Et Tf0 To a solution of ethylacetoacetate (1.3g, lOmmol) in lOml anhydrous dichloromethane was added triethylamine (1.46m1, 10.5mmo1). The reaction was cooled to -78°C under argon to which trifluoromethanesulfonic anhydride (2.96g, lO.Smmo1) was added dropwise via syringe over 5 minutes. Reaction was allowed to warm to room teperature and stirred over night. Next morning the reaction was diluted with 25m1 dichloromethane, organic was washed with 2x50m1 water, 2x50m1 1N HCI, dried over magnesium sulfate, filtered and concentrated. Crude oil was chromatographed on silica gel using 5% EtOAc in hexane as the eluent to give 1) ethyl (E)-3-{[(trifluoromethyl)sulfonyl]-oxy}-2-propenoate (800mg, 60%) as a clear oil: H'NMR (CDCl3) : 1.247-1.282 (t, 3H); 2.471 (s, H); 4.155-4.209 (m, 2H);
S 5.912 (s, H); and 2) ethyl (Z)-3-{[(trifluoromethyl)sulfonyl]-oxy}-2-propenoate (450mg, 30%) as a clear oil: H'NMR (CDCl3) : 1.247-1.283 (t, 3H); 2.131 (s, 3H);
4.18-4.233 (m, 2H); 5.736 (s, H).
Example 44:
CN
To a solution of ethyl (E)-3-{[(trifluoromethyl)sulfonyl]-oxy}-2-propenoate (390mg, 1.49mmo1) in Sml anhydrous dioxane was added potassium phosphate (474mg, 2.24mmo1), 3-cyanophenyl boronic acid (217mg, 1.49mmol), and tetrakis (triphenylphosphine)palladium(0) (43mg, 0.038mmol). Reaction mixture was heated to reflux and stirred overnight. Mixture was filtered through a pad of Celite, diluted with SOmI ethyl acetate, washed with 2x50m1 water, 2x50m1 saturated brine solution, dried over magnesium sulfate, filtered and concentrated in vacuo.
Residue was chromatographed on silica gel using 5% EtOAc in hexane as the eluent to give ethyl (E) 3-(3-cyanophenyl)-2-propenoate (240mg, 71%) as a clear yellow oil after drying. H'NMR (CDC13) : 1.2-1.32 (t, 3H); 2.547 (s, 3H); 4.18-4.24 (m, 2H);
6.113 (s, H); 7.47-7.725 (m, 4H). NOE confirmed stereo orientation.
Example 45:
~02Et CN
To a solution of ethyl (Z)-3-{[(trifluoromethyl)sulfonyl]-oxy}-2-propenoate (330mg, 1.25mmo1) in Sml anhydrous dioxane was added potassium phosphate (398mg, 1.88mmo1), 3-cyanophenyl boronic acid (185mg, 1.25mmol), and tetrakis (triphenylphosphine)palladium(0) (36mg, 0.031mmol). Reaction mixture was heated to reflux and stirred overnight. Mixture was filtered through a pad of Celite, diluted with SOmI ethyl acetate, washed with 2x50m1 water, 2x50m1 saturated brine solution, dried over magnesium sulfate, filtered and concentrated in vacuo.
Residue was chromatographed on silica gel using 5% EtOAc in hexane as the eluent to give ethyl (Z) 3-(3-cyanophenyl)-2-propenoate (240mg, 71 %) as a clear oil after drying.
ES-MS (M+H+): 216.05 Example 46:
O=S~
O
H2N rvn To a solution of 2'-tert-butylaminosulfonyl-4-amino-[1,1']-biphenyl (79mg, 0.26mmol) in 4m1 anhydrous dichloromethane was added a solution of 2M
trimethylaluminum in hexane (0.39m1, 0.78mmo1). Reaction was stirred at room temperature for 20 minutes to which a solution of ethyl (E) 3-(3-cyanophenyl)-propenoate (56mg, 0.26mmo1) in lml anhydrous dichloromethane was added.
Reaction was stirred at room temperature overnight. Reaction was quenched with Sml 1N HCl after which an additional lOml dichloromethane was added. Organic layer was washed with 2x20m1 water, dried over magnesium sulfate, filtered and concentrated to give the (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)but-2-enamide (90mg, 72%) as an off white powder which was sufficiently pure to be used without further purification.
To a solution of (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)but-2-enamide (90mg, 0.19mmo1) in Sml anhydrous methanol cooled in an ice bath was bubbled HCl gas until saturation was achieved. Reaction was allowed to warm to room temperature and stirred overnight. The reaction was then concentrated in vacuo and dried under hi vacuum. The dried residue was dissolved in Sml anhydrous methanol to which ammonium acetate (77mg, lmmol) was added and the reaction heated to reflux for 2 hours. The reaction was concentrated and purified on a 2x25cm Vydac C,g HPLC column to give 3-((lE)-1-methyl-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}vinyl)benzene-carboxamidine (l5mg, 20%) as a fluffy white powder after lyophilization. ES-MS (M+H+): 435.1 Example 47:
a ~~
H
N
H2lv rvn To a solution of 2'-tert-butylaminosulfonyl-4-amino-[1,1']-biphenyl (198mg, 0.65mmo1) in Sml anhydrous dichloromethane was added a solution of 2M
trimethylaluminum in hexane (0.98m1, 1.95mmol). Reaction was stirred at room temperature for 20 minutes to which a solution of ethyl (Z) 3-(3-cyanophenyl)-propenoate (140mg, 0.65mmol) in lml anhydrous dichloromethane was added.
Reaction was stirred at room temperature overnight. Reaction was quenched with Sml 1N HCl after which an additional 20m1 dichloromethane was added. Organic was washed with 2x25m1 water, dried over magnesium sulfate and concentrated to give (2Z)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)but-2-enamide (200mg, 65%) as a light brown residue which was sufficiently pure to be used without further purification.
To a solution of (2Z)-N-[4-(2-{[(tent-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)but-2-enamide (90mg, 0.19mmo1) in Sml anhydrous methanol cooled in an ice bath was bubbled HCl gas until saturation was achieved. Reaction was allowed to warm to room temperature and stirred overnight. The reaction was then concentrated in vacuo and dried under hi vacuum. The dried residue was dissolved in Sml anhydrous methanol to which ammonium acetate (144mg, 2mmo1) was added and the reaction heated to reflux for 2 hours. The reaction was concentrated and purified on a 2x25cm Vydac C,$ HPLC column to give 3-((1Z)-1-methyl-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}vinyl)-benzenecarboxamidine (35mg, 20%) as a fluffy white powder after lyophilization. ES-MS (M+H+): 435.1 Example 48:
a H
N
HZIv nn To a solution of the 3-((1Z)-1-methyl-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}vinyl)-benzenecarboxamidine (Smg, 0.01 l5mmol) in 4m1 methanol was added 10% Pd on carbon (2mg). Mixture was treated with SOpsi hydrogen on the PARK apparatus for lhr. Reaction was filtered through a pad of Celite, concentrated and lyophilized to give 3-(1-methyl-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}-ethyl)benzenecarboxamidine (3mg, 60%) as a fluffy white powder. ES-MS (M+H+): 437.1 Example 49:
Tf0 C02Et To a solution of ethyl trifluoroacetoacetate (5g, 27.2mmo1) in 20m1 anhydrous dichloromethane was added triethylamine (5.7m1, 40.7mmo1). Reaction was cooled . under argon to -78°C to which trifluoro-methanesulfonic anhydride (ll.Sg, 10.5mmo1) was added dropwise via syringe over 5 minutes. Reaction was allowed to warm to room temperature and stirred over night. Next morning the reaction was diluted with 25m1 dichloromethane, organic was washed with 2x50m1 water, 2x50m1 1N HCI, dried over magnesium sulfate, filtered and concentrated in vacuo.
Crude oil was chromatographed on silica gel using 5% EtOAc in hexane as the eluent to give ethyl (Z)-4,4,4-trifluoro-3-{[(trifluoromethyl)sulfonyl]-oxy}-2-butenoate (7.7g, 90%) as a clear light yellow oil after drying. H'NMR (CDC13) . 1.31-1.35 (t, 3H);
4.33-4.35 (m, 2H); 6.535 (s, H).
Example 50:
C02Et CN
To a solution of ethyl (Z)-4,4,4-trifluoro-3-{[(trifluoromethyl)sulfonyl]-oxy}-butenoate (250mg, 0.79mmo1) in Sml anhydrous dioxane was added potassium phosphate (251mg, 1.19mmo1), 3-cyanophenyl boronic acid (116mg, 0.79mmo1), and tetrakis (triphenylphosphine)palladium(0) (23mg, 0.02mmo1). Reaction mixture was heated to reflux and stirred overnight. Mixture was filtered through a pad of Celite, diluted with SOmI ethyl acetate, washed with 2x50m1 water, 2x50m1 saturated brine solution, dried over magnesium sulfate, filtered and concentrated in vacuo.
Residue was chromatographed on silica gel using 20% EtOAc in hexane as the eluent to give ethyl (2E)-3-(3-cyanophenyl)-4,4,4-trifluorobut-2-enoate (150mg, 79%) as a yellow residue after drying. H'NMR (CDC13) : 1.107-1.142 (t, 3H);
4.05-4.107 (m, 2H); 6.684 (s, H); 7.38-7.72 (m, 4H).
Example 51:
HZN
O=S O
H
N
HZw nn To a solution of 2'-tert-butylaminosulfonyl-4-amino-[1,1']-biphenyl (79mg, 0.26mmo1) in 5m1 anhydrous dichloromethane was added a solution of 2M
trimethylaluminum in hexane (0.39m1, 0.78mmo1). Reaction was stirred at room temperature for 20 minutes to which a solution of ethyl (Z) 3-(3-cyanophenyl)-4,4,4-trifluoro-2-butenoate (70mg, 0.26mmo1) in lml anhydrous dichloromethane was added. Reaction was stirred at room temperature overnight. Reaction was quenched with 5m1 1N HCl after which an additional 20m1 dichloromethane was added.
Organic was washed with 2x25m1 water, dried over magnesium sulfate, filtered and concentrated to give (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)pheriyl]-3-(3-cyanophenyl)-4,4,4-trifluorobut-2-enamide (120mg, 88%) as a yellow foam which was sufficiently pure to be used without further purification.
To a solution of (2E)-N-[4-(2-{[(tent-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)-4,4,4-trifluorobut-2-enamide (90mg, 0.19mmo1) in lOml 1:1 ethyl acetate:anhydrous methanol cooled to -78°C was bubbled HCl gas until saturation was achieved. Reaction was placed in the refrigerator at 0°C over the weekend.
The reaction was then concentrated in vacuo and dried under hi vacuum. The dried methyl imidate residue was dissolved in 5m1 anhydrous methanol to which ammonium acetate (144mg, 2mmo1) was added and the reaction heated to reflex for 2 hours. The reaction was concentrated then treated with lOml trifluoroacetic acid for 2hrs, concentrated and purified on a 2x25cm Vydac C,8 HPLC column to give (( 1 E)-2- {N-[4-(2-sul famoylphenyl)phenyl] carbamoyl } -1-(trifluoromethyl)vinyl)benzenecarboxamidine (57mg, 47%) as a fluffy white powder after lyophilization. ES-MS (M+H+): 489.15 Example 52:
u_~
H
N
H2W nn To a solution of 3-((lE)-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}-1-(trifluoromethyl)vinyl)-benzenecarboxamidine (lOmg, 0.02mmo1) in 4m1 methanol was added 10% Pd on carbon (2mg). Mixture was treated with hydrogen at 1 atmosphere under balloon for lhr. Reaction was filtered through a pad of Celite, concentrated and lyophilized to give 3-[2,2,2-trifluoro-1-({N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}-methyl)ethyl]benzenecarboxamidine (8mg, 82%) as a fluffy white powder. ES-MS (M+H+): 491.1 Example 53:
/C02Et CN
To a solution of ethyl (Z) 3-(3-cyanophenyl)-2-propenoate (2g, 9.3mmo1) in SOmI
carbon tetrachloride was added N-bromosuccinimide (1.748, 9.77mmo1) and benzoyl peroxide (40mg, 0.165mmo1). Reaction mixture was heated to reflux and stirred over night. Reaction was allowed to cool to room temperature to which SOmI
dichloromethane was added. Organic was washed with 2x50m1 water, dried over magnesium sulfate, filtered and concentrated in vacuo. Crude residue was chromatographed on silica gel using 2.5% EtOAc in hexane as the eluent to give ethyl (Z) 3-(3-cyanophenyl)-4-bromo-2-butenoate (0.77g, 29%) as a clear oil (note:
NOE experiment showed compound isomerized during bromination). H'NMR
(CDC13) : 1.311-1.347 (t, 3H); 4.239-4.292 (m, 2H); 4.92 (s, 2H); 6.18 (s, H);
7.514-7.801 (m, 4H). ES-MS (M+H+): 293.95 and 296.0 Example 54:
C02Et N~N
To a solution of ethyl (Z) 3-(3-cyanophenyl)-4-bromo-2-butenoate (103mg, 0.35mmo1) in Sml anhydrous di-methylformamide was added pyrazole (24mg, 0.35mmo1) and cesium carbonate (228mg, 0.7mmo1). Reaction mixture was stirred for 1.5 hours at room temperature after which 25m1 ethyl acetate was added.
S Organic was washed with 3x25m1 water, 3x50m1 saturated brine solution, dried over magnesium sulfate, filtered and concentrated to give ethyl (Z)-3-(3-cyanophenyl)-4-(1H 1-pyrazolyl)-2-butenoate (70mg, 71%) as a brown residue which was sufficiently pure to be used without further purification. ES-MS (M+H+): 282.1 Example SS:
a ~i NON n N
H
To a solution of 2'-tert-butylaminosulfonyl-4-amino-[1,1']-biphenyl (76mg, 0.25mmo1) in 4m1 anhydrous dichloromethane was added a solution of 2M
trimethylaluminum in hexane (0.38m1, 0.75mmo1). Reaction was stirred at room temperature for 20 minutes to which a solution of ethyl (Z)-3-(3-cyanophenyl)-(1H 1-pyrazolyl)-2-butenoate (70mg, 0.25mmo1) in lml anhydrous dichloromethane was added. Reaction was stirred at room temperature overnight. Reaction was quenched with Sml 1N HCl after which an additional 20m1 dichloromethane was added. Organic was washed with 2x20m1 water, dried over magnesium sulfate and concentrated to give the tButyl nitrile of the title compound (120mg, 89%) as a brown foam which was sufficiently pure to use in the next step.
To a solution of the above nitrite compound (120mg, 0.22mmo1) in lOml 1:1 ethyl acetate : anhydrous methanol cooled to -78°C was bubbled HCl gas until saturation was achieved. Reaction was allowed to warm to room temperature and stirred overnight. The reaction was then concentrated in vacuo and dried under hi vacuum.
The dried methyl imidate residue was dissolved in Sml anhydrous methanol to which ammonium acetate (77mg, lmmol) was added and the reaction heated to reflux for 2 hours. The reaction was concentrated, then treated with trifluoroacetic acid (lOml) for 2 hours, concentrated and purified on a 2x25cm Vydac C,8 HPLC
column to give 3-((1Z)-1-(pyrazolylmethyl)-2-{N-[4-(2-sulfamoylphenyl)phenyl]-carbamoyl}vinyl)benzenecarboxamidine (lOmg, 9%) as a fluffy white powder after lyophilization. ES-MS (M+H+): 501.1 Example 56:
N~ 1 vN
O
CN
To a solution of 3-acetobenzonitrile (5g, 0.0344mo1) in 45m1 glacial acetic acid was added pyridinium tribromide (11.3g, 0.0355mo1). Reaction was stirred at room temperature under argon overnight. Reaction was then quenched with a saturated sodium sulfite solution (20m1) and extracted with 3x25m1 dichloromethane.
Combined organic phases were washed with 2x25m1 water, dried over magnesium sulfate, filtered and concentrated in vacuo. Crude oil was chromatographed on silica gel using 5% EtOAc in hexane as the eluent to give 3-(2-bromoacetyl) benzonitrile (4.5g, 58%) as a white solid. H'NMR (CDCl3) : 4.371-4.403 (s, 2H); 7.613-7.664 (m, H); 7.838-7.888 (m, H); 8.192-8.261 (m, 2H).
To a solution of 3-(2-bromaceto)benzonitrile (SOOmg, 2.23mmo1) in Sml dichloromethane was added pyrazole (304mg, 4.46mmo1) and triethylamine (0.31m1, 2.23mmol). Reaction was stirred at room temperature over night. Reaction was then diluted with 20m1 dichloromethane, washed with 2x25m1 water, 2x25m1 1N
HCI, dried over magnesium sulfate, filtered and concentrated in vacuo. Crude residue was chromatographed on silica gel using 2.5% EtOAc in hexane to give 3-[2-(IH 1-pyrazolyl)acetyl]benzonitrile (330mg, 70%) as a clear oil after drying. ES-MS (M+H+): 212.05 Example 57:
~02Me To a solution of bis(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate (0.39m1, 1.87mmol) in Sml anhydrous tetrahydrofuran was added a solution of 18-crown-6 (2g, 7.8mmo1) in Sml anhydrous tetrahydrofuran. Reaction was cooled to -78° C to which a O.SM solution of potassium bis(trimethylsilyl)amide in toluene (0.93m1, 1.87mmol) was added all at once. The reaction mixture was stirred at -78°
C for 20 minutes after which a solution of 3-[2-(1H 1-pyrazolyl)acetyl]-benzonitrile (330mg, 1.56mmo1) in Sml anhydrous tetrahydrofuran was added dropwise over several minutes. Reaction was gradually allowed to warm to room temperature and stirred for S hours. Reaction was then quenched with a saturated ammonium chloride solution (lOml) and extracted with 2x25m1 diethyl ether. Combined organic layers were washed with 2x25m1 water, 2x25m1 saturated brine solution, dried over magnesium sulfate, filtered and concentrated to a brown residue.
Crude residue was chromatographed on silica gel using a gradient of 5% EtOAc in hexane containing 0.1 % triethylamine to 20% EtOAc in hexane contaning 0.1 N~
triethylamine to give methyl (E)-3-(3-cyanophenyl)-4-(1H 1-pyrazolyl)-2-butenoate (135mg, 32%) as a clear oil after drying. H'NMR (CDC13) : 3.521 (s, #H); 4.98 (s, 2H); 5.694 (s, H); 6.237-6.247 (t, H); 7.296-7.593 (m, 6H). NOE experiment confirmed stereoconfiguration.
Example 58:
N ~ a ~i N
H
N
HZIv rvn To a solution of 2'-tert-butylaminosulfonyl-4-amino-[1,1']-biphenyl (lOSmg, 0.34mmo1) in 4m1 anhydrous dichloromethane was added a solution of 2M
trimethylaluminum in hexane (O.SmI, 1.02mmo1). Reaction was stirred at room temperature for 20 minutes to which a solution of methyl (E)-3-(3-cyanophenyl)-(1H 1-pyrazolyl)-2-butenoate (90mg, 0.34mmo1) in lml anhydrous dichloromethane was added. Reaction was stirred at room temperature overnight. Reaction was quenched with Sml 1N HCl after which an additional 20m1 dichloromethane was added. Organic was washed with 2x20m1 water, dried over magnesium sulfate, filtered and concentrated to give (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)but-2-enamide (155mg, 85%) as an off white foam which was sufficiently pure to be used without further purification.
To a solution of (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)but-2-enamide (155mg, 0.287mmol) in lOml 1:1 ethyl acetate:anhydrous methanol cooled to -78°C was bubbled HCl gas until saturation was achieved. Reaction was allowed to warm to room temperature and stirred overnight. The reaction was then concentrated in vacuo and dried under hi vacuum.
The dried methyl imidate residue was dissolved in Sml anhydrous methanol to which ammonium acetate (77mg, lmmol) was added and the reaction heated to reflux for 2 hours. The reaction was concentrated, treated with trifluoroacetic acid S (lOml) for 2hrs, concentrated and purified on a 2x25cm Vydac C,$ HPLC column to give 3-((lE)-1-(pyrazolylmethyl)-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}vinyl)benzenecarboxamidine (40mg, 28%) as a fluffy white powder after lyophilization. ES-MS (M+H+): 501.1 Example 59:
N ~ H2N
O
N ~ O S~
H
N
H2lv rv n To a solution of 3-((lE)-1-(pyrazolylmethyl)-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}vinyl)-benzenecarboxamidine (Smg, O.Olmmol) in 4m1 methanol was added 10% Pd on carbon (lmg). Mixture was treated with hydrogen at 1 atmosphere under balloon for lhr. Reaction was filtered through a pad of Celite, concentrated and lyophilized to give 3-(1-(pyrazolylmethyl)-2-f N-[4-(2-sulfamoylphenyl)phenyl]-carbamoyl}ethyl)benzenecarboxamidine (Smg, 100%) as a fluffy white powder. ES-MS (M+H+): 503.1 Example 60:
2Et To a solution of ethyl B-oxo-3-furanpropionate (1g, 5.49mmo1) in Sml anhydrous dichloromethane was added triethylamine (0.847m1, 6.04mmo1). Reaction was cooled under argon to -78°C to which trifluoromethanesulfonic anhydride (1.02m1, 6.04mmo1) was added dropwise via syringe over 5 minutes. Reaction was allowed to warm to room temperature and stirred over night. Next morning the reaction was diluted with 25m1 dichloromethane, organic was washed with 2x50m1 water, 2x50m1 1N HCI, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude oil was chromatographed on silica gel using 20% EtOAc in hexane as the eluent to give ethyl (Z)-3-(2-furyl)-3-{[(trifluoromethyl)sulfonyl]-oxy}-2-propenoate (1.6g, 93%) as a light brown solid after drying. H'NMR (CDC13) :
1.31-1.35 (t, 3H); 4.26-4.314 (m, 2H); 6.065 (s, H); 6.522 (s, H); 7.47 (s, H);
7.76 (s, H).
Example 61:
~OZEt CN
To a solution of ethyl (Z)-3-(2-furyl)-3-{[(trifluoromethyl)sulfonyl]-oxy}-2-propenoate (SOOmg, 1.59mmo1) in 7m1 anhydrous dioxane was added potassium phosphate (506mg, 2.4mmo1), 3-cyanophenyl boronic acid (234mg, 1.59mmo1), and tetrakis (triphenylphosphine)palladium(0) (46mg, 0.04mmo1). Reaction mixture was heated to reflux and stirred overnight. Mixture was filtered through a pad of Celite, diluted with SOmI ethyl acetate, washed with 2xSOm1 water, 2x50m1 saturated brine solution, dried over magnesium sulfate, filtered and concentrated in vacuo.
The crude residue was chromatographed on silica gel using a gradient from 5% EtOAc in hexane to 10% EtOAc in hexane as the eluent to give ethyl (E) 3-(3-cyanophenyl)-3-(2-furyl)-2-propenoate (100mg, 24%) as a clear yellow oil after drying. H'NMR
(CDC13) : 1.1-1.14 (t, 3H); 4,016-4.035 (m, 2H); 5.293 (s, H); 7.45-7.549 (m, 3H);
7.669 (m, H). ES-MS (M+H+): 268.05 Example 62:
HzN O
O=S~
H
N
To a solution of 2'-tButylaminosulfonyl-4-amino-[1,1']-biphenyl (102mg, 0.336mmo1) in 4m1 anhydrous dichloromethane was added a solution of 2M
trimethylaluminum in hexane (O.SmI, 1.Ommo1). Reaction was stirred at room temperature for 20 minutes to which a solution of ethyl (E) 3-(3-cyanophenyl)-3-(2-furyl)-2-propenoate (90mg, 0.336mmo1) in lml anhydrous dichloromethane was added. Reaction was stirred at room temperature overnight. Reaction was quenched with Sml 1N HCl after which an additional 20m1 dichloromethane was added.
Organic was washed with 2x20m1 water, dried over magnesium sulfate and concentrated to give (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)-3-(2-furyl)prop-2-enamide (200mg, 112%) as a brown foam which was sufficiently pure to be used without further purification.
To a solution of (2E)-N-[4-(2-{[(tent-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)-3-(2-furyl)prop-2-enamide (176mg, 0.336mmol) in lOml 1:1 ethyl acetate:anhydrous methanol cooled to -78°C was bubbled HCl gas until saturation was achieved. Reaction was allowed to warm to room temperature and stirred overnight. The reaction was then concentrated in vacuo and dried under hi vacuum.
The dried methyl imidate residue was dissolved in Sml anhydrous methanol to which ammonium acetate (144mg, 2mmo1) was added and the reaction heated to reflux for 2 hours. The reaction was concentrated, treated with trifluoroacetic acid (lOml) for 2hrs, concentrated and purified on a 2x25cm Vydac C,g HPLC column to give 3-((lE)-1-(2-furyl)-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}vinyl)benzenecarboxamidine (60mg, (37%) as a fluffy off white powder after lyophilization. ES-MS (M+H+): 487.15 Example 63:
HZN
O=S O
H
N
To a solution of 3-((lE)-1-(2-furyl)-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}vinyl)benzenecarboxamidine (lOmg, 0.02mmo1) in 4m1 methanol was added 10% Pd on carbon (2mg). Mixture was treated with hydrogen at 1 atmosphere under balloon for lhr. Reaction was filtered through a pad of Celite, concentrated and lyophilized to give 3-(1-(2-fiuyl)-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}ethyl)benzenecarboxamidine (9mg, 90%) as a fluffy white powder. ES-MS (M+H+): 489.15 Example 64:
OMe Tf0 C02Me To a solution of methyl 4-methoxy-3-oxobutanoate (5g, 34.2mmo1) in 20m1 anhydrous dichloromethane was added triethylamine (5.24m1, 37.6mmo1). Reaction was cooled under argon to -78°C to which trifluoromethane-sulfonic anhydride (10.6gm1, 37.6mmo1) was added dropwise via syringe over 5 minutes. Reaction was allowed to warm to room temperature and stirred over night. Next morning the reaction was diluted with 25m1 dichloromethane, organic was washed with 2x50m1 water, 2x50m1 1N HCI, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude oil was chromatographed on silica gel using a gradient of 5%
EtOAc in hexane to 10% EtOAc in hexane as the eluent to give methyl (Z)-4-methoxy-3- f [(trifluoromethyl)sulfonyl]-oxy}-2-butenoate (5.1g, 54%) as a clear colorless oil after drying. H'NMR (CDC13) : 3.342 (s, 3H); 3.711 (s, 3H); 3.99 (s, H); 6.02 (s, H).
Example 65:
~OZMe CN
To a solution of methyl (Z)-4-methoxy-3-{[(trifluoromethyl)sulfonyl]-oxy}-2-butenoate (246mg, l.Ommo1) in Sml anhydrous dioxane was added potassium phosphate (318mg, l.Smmol), 3-cyanophenyl boronic acid (162mg, l.Ommo1), and tetrakis (triphenylphosphine)palladium(0) (29mg, 0.0251mmo1). Reaction mixture was heated to reflux and stirred overnight. Mixture was filtered through a pad of Celite, diluted with 20m1 ethyl acetate. Organic was washed with 2x20m1 water, 2x20m1 saturated brine solution, dried over magnesium sulfate, filtered and concentrated in vacuo to give methyl (E)-3-(3-cyanophenyl)-4-methoxy-2-butenoate (220mg, 75%) as a clear brown oil which was sufficiently pure to be used without further purification. ES-MS (M+H+): 232.1 Example 66:
O
OMe O S
H
N
H2N rvn To a solution of 2'-tButylaminosulfonyl-4-amino-[1,1']-biphenyl (lOSmg, 0.35mmo1) in 4m1 anhydrous dichloromethane was added a solution of 2M
trimethylaluminum in hexane (0.53m1, I.OSmmo1). Reaction was stirred at room temperature for 20 minutes to which a solution of methyl (E) 3-(3-cyanophenyl)-methoxy-2-butenoate (80mg, 0.35mmo1) in lml anhydrous dichloromethane was added. Reaction was stirred at room temperature overnight. Reaction was quenched with Sml 1N HCl after which an additional 20m1 dichloromethane was added.
Organic was washed with 2x20m1 water, dried over magnesium sulfate and concentrated to give (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)-4-methoxybut-2-enamide (150mg, 85%) as a white foam after drying which was sufficiently pure to be used without further purification.
To a solution of (2E)-N-[4-(2-{[(tent-butyl)amino]sulfonyl)phenyl)phenyl]-3-(3-cyanophenyl)-4-methoxybut-2-enamide (150mg, 0.298mmo1) in lOml 1:1 ethyl acetate:anhydrous methanol cooled to -78°C was bubbled HCl gas until saturation was achieved. Reaction was allowed to warm to room temperature and stirred overnight. The reaction was then concentrated in vacuo and dried under hi vacuum.
The dried methyl imidate residue was dissolved in Sml anhydrous methanol to which ammonium acetate (77mg, lmmol) was added and the reaction heated to reflux for 2 hours. The reaction was concentrated, treated with trifluoroacetic acid (lOml) for 2hrs, concentrated and purified on a 2x25cm Vydac C,g HPLC column to give 3-((lE)-1-(methoxymethyl)-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}vinyl)benzenecarboxamidine (34mg, (25%) as a fluffy off white powder after lyophilization. ES-MS (M+H+): 465.1 S
S Example 67:
u_N
H
N
H2fv nn To a solution of 3-((lE)-1-(methoxymethyl)-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}vinyl)-benzenecarboxamidine (Smg, O.Olmmol) in 4m1 methanol was added 10% Pd on carbon (lmg). Mixture was treated with hydrogen at 1 atmosphere under balloon for lhr. Reaction was filtered through a pad of Celite, concentrated and lyophilized to give 3-(1-(methoxymethyl)-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}-ethyl)benzenecarboxamidine (Smg, 100%) as a fluffy white powder. ES-MS (M+H'): 467.15 BIOLOGICAL ACTIVITY EXAMPLES
Evaluation of the compounds of this invention is guided by in vitro protease activity assays (see below) and in vivo studies to evaluate antithrombotic efficacy, and effects on hemostasis and hematological parameters.
The compounds of the present invention are dissolved in buffer to give solutions containing concentrations such that assay concentrations range from 0 to 100 ~M. In the assays for thrombin, prothrombinase and factor Xa, a synthetic chromogenic substrate is added to a solution containing test compound and the enzyme of interest and the residual catalytic activity of that enzyme is determined spectrophotometrically. The IC50 of a compound is determined from the substrate turnover. The IC50 is the concentration of test compound giving 50% inhibition of the substrate turnover. The compounds of the present invention desirably have an ICSO of less than 500 nM in the factor Xa assay, preferably less than 200 nM, and more preferred compounds have an IC50 of about 100 nM or less in the factor Xa assay. The compounds of the present invention desirably have an IC50 of less than 4.0 ~,M in the prothrombinase assay, preferably less than 200 nM, and more preferred compounds have an IC50 of about 10 nM or less in the prothrombinase assay. The compounds of the present invention desirably have an IC50 of greater than 1.0 uM in the thrombin assay, preferably greater than 10.0 ~.M, and more preferred compounds have an IC50 of greater than 100.0 pM in the thrombin assay.
Amidolytic Assays for determining_protease inhibition activity The factor Xa and thrombin assays are performed at room temperature, in 0.02 M Tris~HCl buffer, pH 7.5, containing 0.15 M NaCI. The rates of hydrolysis of the para-nitroanilide substrate S-2765 (Chromogenix) for factor Xa, and the substrate Chromozym TH (Boehringer Mannheim) for thrombin following preincubation of the enzyme with inhibitor for 5 minutes at room temperature, and were determined using the Softmax 96-well plate reader (Molecular Devices), monitored at 405 nm to measure the time dependent appearance of p-nitroaniline.
The prothrombinase inhibition assay is performed in a plasma free system with modifications to the method described by Sinha, U. et al., Thromb. Res., Z, 427-436 (1994). Specifically, the activity of the prothrombinase complex is determined by measuring the time course of thrombin generation using the p-nitroanilide substrate Chromozym TH. The assay consists of preincubation ( 5 minutes) of selected compounds to be tested as inhibitors with the complex formed from factor Xa (0.5 nM), factor Va (2 nM), phosphatidyl serine:phosphatidyl choline (25:75, 20 pM) in 20 mM Tris~HCl buffer, pH 7.5, containing 0.15 M NaCI, 5 mM
CaCl2 and 0.1% bovine serum albumin. Aliquots from the complex-inhibitor mixture are added to prothrombin ( 1 nM) and Chromozym TH (0.1 mM). The rate of substrate cleavage is monitored at 405 nm for two minutes. Eight different concentrations of inhibitor are assayed in duplicate. A standard curve of thrombin generation by an equivalent amount of untreated complex are used for determination of percent inhibition.
Antithrombotic Efficac~in a Rabbit Model of Venous Thrombosis A rabbit deep vein thrombosis model as described by Hollenbach, S. et al., Thromb. Haemost. 71, 357-362 (1994), is used to determine the in-vivo antithrombotic activity of the test compounds. Rabbits are anesthetized with LM. injections of Ketamine, Xylazine, and Acepromazine cocktail. A standardized protocol consists of insertion of a thrombogenic cotton thread and copper wire apparatus into the abdominal vena cava of the anesthetized rabbit. A non-occlusive thrombus is allowed to develop in the central venous circulation and inhibition of thrombus growth is used as a measure of the antithrombotic activity of the studied compounds. Test agents or control saline are administered through a marginal ear vein catheter. A femoral vein catheter is used for blood sampling prior to and during steady state infusion of test compound.
Initiation of thrombus formation begins immediately after advancement of the cotton thread apparatus into the central venous circulation. Test compounds are administered from time = 30 min to time = 150 min at which the experiment is terminated. The rabbits are euthanized and the thrombus excised by surgical dissection and characterized by weight and histology.
Blood samples are analyzed for changes in hematological and coagulation parameters.
Effects of Compounds in Rabbit Venous Thrombosis model Administration of compounds in the rabbit venous thrombosis model demonstrates antithrombotic efficacy at the higher doses evaluated. There are no significant effects of the compound on the aPTT and PT prolongation with the highest dose (100 ~g/kg + 2.57 ~g/kg/min). Compounds have no significant effects on hematological parameters as compared to saline controls. All measurements are an average of all samples after steady state administration of vehicle or (D)-Arg-Gly-Arg-thiazole. Values are expressed as mean + SD.
Without further description, it is believed that one of ordinary skill in the art can, using the preceding description and the following illustrative examples, make and utilize the compounds of the present invention and practice the claimed methods.
Claims (15)
1. A compound according to the formula:
A-Y-D-E-G-J-K-L
wherein:
A is selected from:
(a) C1-C6 alkyl;
(b) C3-C8-cycloalkyl;
(c) phenyl, which is independently substituted with 0-2 R1 substituents;
(d) naphthyl, which is independently substituted with 0-2 R1' substituents;and (e) a monocyclic or fused bicyclic heterocyclic ring system having from to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R1 substituents;
R1 is selected from:
Halo, C,1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl,-CN, -NO2, (CH2)m NR2R3, SO2NR2R3, SO2R2, CF3, OR2, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, C1-C4 alkyl, -CN C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl and -NO2;
R2 and R3 are independently selected from the group consisting of:
H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN, and -NO2;
m is an integer of 0-2;
Y is a member selected from the group consisting of:
a direct link, -C(=O)-, -N(R4)-, -C(=O)-N(R4)-, -N(R4)-C(=O)-, -SO2 , -O-, -SO2-N(R4)- and -N(R4)-SO2-;
R4 is selected from:
H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN, and -NO2;
D is a direct link or is a member selected from the group consisting of:
(a) phenyl, which is independently substituted with 0-2 R1a substituents;
(b) naphthyl, which is independently substituted with 0-2 R1a substituents; and (c) a monocyclic or fused bicyclic heterocyclic ring system having from to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R1a substituents;
R1a is selected from:
Halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN, -NO2, (CH2)m NR2a R3a, SO2NR2a R3a, SO2R2a, CF3, OR2a, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN and -NO2.
R2a and R3a are independently selected from the group consisting of H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN and -NO2;.
E is a member selected from the group consisting of:
-N(R5)-C(=O)-, -C(=O)-N(R5)-, -N(R5)-C(=O)-N(R6)-, -SO2-N(R5)-, -N(R5)-SO2-N(R6)- and N(R5)-SO2-N(R6)-C(=O)-;
R5 and R6 are independently selected from:
H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl, C0-4alkylnaphthyl, C0-4alkylheteroaryl, C1-4alkylCOOH and C1-4alkylCOOC1-4alkyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl, naphthyl and heteroaryl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN and -NO2;
G is selected from:
-CR7R8- and -CR7R8a-CR7b R8b-wherein R7, R8, R7a, R8a, R7b and R8b are independently a member selected from from the group consisting of:
hydrogen, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkyl-C3-8cycloalkyl, C0-4alkylphenyl, C0-4alkylnaphthyl, -OR9, -C0-4alkylCOOR9, -C0-4alkylC(=O)NR9R10, -C0-4alkylC(=O)NR9-CH2-CH2-O-R10, -C0-4alkylC(=O)NR9(-CH2-CH2-O-R10-)2, -N(R9)COR10, -N(R9)C(=O)R10, -N(R9)SO2R10, and a naturally occurring or synthetic amino acid side chain, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkyl-C3-8cycloalkyl, -CN and -NO2;
R9 and R10 are independently selected from:
H, C1-4alkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkyl-C3-8cycloalkyl, -CN and -NO2, and wherein R9 and R10 taken together can form a 5-8 membered heterocylic ring;
J is a member selected from the group consisting of:
a direct link, -CH(R11)- and -CH(R11)-CH2-;
R11 is a member selected from the group consisting of:
hydrogen, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkyl-C3-8cycloalkyl, C0-4alkylphenyl, C0-4alkylnaphthyl, C0-4alkylheterocyclic ring having from 1 to 4 hetero ring atoms selected from the group consisting of N, O and S, CH2COOC1-4alkyl, CH2COOC1-4alkylphenyl and CH2COOC1-4alkylnaphthyl;
K is a member selected from the group consisting of:
(a) phenyl, which is independently substituted with 0-2 R1b substituents;
(b) naphthyl, which is independently substituted with 0-2 R1b substituents; and (c) a monocyclic or fused bicyclic heterocyclic ring system having from to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R1b substituents;
R1b is selected from:
Halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkyl-C3-8cycloalkyl, -CN, -NO2, NR2b R3b, SO2NR2b R3b, SO2R2b, CF3, OR2b, O-CH2-CH2-OR2b, O-CH2-COOR2b, N(R2b)-CH2-CH2-OR2b, N(-CH2-CH2-OR2b)2, N(R2b)-C(=O)R3b, N(R3b)-SO3-R3b, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN and -NO2;
R2b and R3b are independently selected from the group consisting of:
H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN and -NO2;
L is selected from:
H -CN, C(=O)NR12R13, (CH2)n NR12R13, C(=NR12)NR12R13, NR12R13, OR12, -NR12C(=NR12)NR12R13, and NR12C(=NR12)-R13;
R12 and R13 are independently selected from:
hydrogen, -OR14, -NR14R15, C1-4alkyl, C0-4alkylphenyl, C0-4alkylnaphthyl, COOC1-4alkyl, COO-C0-4alkylphenyl and COO-C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN, and -NO2;
R14 and R15 are independently selected from:
H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN, and -NO2;
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
A-Y-D-E-G-J-K-L
wherein:
A is selected from:
(a) C1-C6 alkyl;
(b) C3-C8-cycloalkyl;
(c) phenyl, which is independently substituted with 0-2 R1 substituents;
(d) naphthyl, which is independently substituted with 0-2 R1' substituents;and (e) a monocyclic or fused bicyclic heterocyclic ring system having from to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R1 substituents;
R1 is selected from:
Halo, C,1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl,-CN, -NO2, (CH2)m NR2R3, SO2NR2R3, SO2R2, CF3, OR2, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, C1-C4 alkyl, -CN C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl and -NO2;
R2 and R3 are independently selected from the group consisting of:
H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN, and -NO2;
m is an integer of 0-2;
Y is a member selected from the group consisting of:
a direct link, -C(=O)-, -N(R4)-, -C(=O)-N(R4)-, -N(R4)-C(=O)-, -SO2 , -O-, -SO2-N(R4)- and -N(R4)-SO2-;
R4 is selected from:
H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN, and -NO2;
D is a direct link or is a member selected from the group consisting of:
(a) phenyl, which is independently substituted with 0-2 R1a substituents;
(b) naphthyl, which is independently substituted with 0-2 R1a substituents; and (c) a monocyclic or fused bicyclic heterocyclic ring system having from to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R1a substituents;
R1a is selected from:
Halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN, -NO2, (CH2)m NR2a R3a, SO2NR2a R3a, SO2R2a, CF3, OR2a, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN and -NO2.
R2a and R3a are independently selected from the group consisting of H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN and -NO2;.
E is a member selected from the group consisting of:
-N(R5)-C(=O)-, -C(=O)-N(R5)-, -N(R5)-C(=O)-N(R6)-, -SO2-N(R5)-, -N(R5)-SO2-N(R6)- and N(R5)-SO2-N(R6)-C(=O)-;
R5 and R6 are independently selected from:
H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl, C0-4alkylnaphthyl, C0-4alkylheteroaryl, C1-4alkylCOOH and C1-4alkylCOOC1-4alkyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl, naphthyl and heteroaryl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN and -NO2;
G is selected from:
-CR7R8- and -CR7R8a-CR7b R8b-wherein R7, R8, R7a, R8a, R7b and R8b are independently a member selected from from the group consisting of:
hydrogen, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkyl-C3-8cycloalkyl, C0-4alkylphenyl, C0-4alkylnaphthyl, -OR9, -C0-4alkylCOOR9, -C0-4alkylC(=O)NR9R10, -C0-4alkylC(=O)NR9-CH2-CH2-O-R10, -C0-4alkylC(=O)NR9(-CH2-CH2-O-R10-)2, -N(R9)COR10, -N(R9)C(=O)R10, -N(R9)SO2R10, and a naturally occurring or synthetic amino acid side chain, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkyl-C3-8cycloalkyl, -CN and -NO2;
R9 and R10 are independently selected from:
H, C1-4alkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkyl-C3-8cycloalkyl, -CN and -NO2, and wherein R9 and R10 taken together can form a 5-8 membered heterocylic ring;
J is a member selected from the group consisting of:
a direct link, -CH(R11)- and -CH(R11)-CH2-;
R11 is a member selected from the group consisting of:
hydrogen, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkyl-C3-8cycloalkyl, C0-4alkylphenyl, C0-4alkylnaphthyl, C0-4alkylheterocyclic ring having from 1 to 4 hetero ring atoms selected from the group consisting of N, O and S, CH2COOC1-4alkyl, CH2COOC1-4alkylphenyl and CH2COOC1-4alkylnaphthyl;
K is a member selected from the group consisting of:
(a) phenyl, which is independently substituted with 0-2 R1b substituents;
(b) naphthyl, which is independently substituted with 0-2 R1b substituents; and (c) a monocyclic or fused bicyclic heterocyclic ring system having from to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R1b substituents;
R1b is selected from:
Halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkyl-C3-8cycloalkyl, -CN, -NO2, NR2b R3b, SO2NR2b R3b, SO2R2b, CF3, OR2b, O-CH2-CH2-OR2b, O-CH2-COOR2b, N(R2b)-CH2-CH2-OR2b, N(-CH2-CH2-OR2b)2, N(R2b)-C(=O)R3b, N(R3b)-SO3-R3b, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN and -NO2;
R2b and R3b are independently selected from the group consisting of:
H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN and -NO2;
L is selected from:
H -CN, C(=O)NR12R13, (CH2)n NR12R13, C(=NR12)NR12R13, NR12R13, OR12, -NR12C(=NR12)NR12R13, and NR12C(=NR12)-R13;
R12 and R13 are independently selected from:
hydrogen, -OR14, -NR14R15, C1-4alkyl, C0-4alkylphenyl, C0-4alkylnaphthyl, COOC1-4alkyl, COO-C0-4alkylphenyl and COO-C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN, and -NO2;
R14 and R15 are independently selected from:
H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN, and -NO2;
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
2. A compound of claim 1, wherein:
A is selected from:
(a) C1-C6 alkyl;
(b) C3-C8-cycloalkyl;
(c) phenyl, which is independently substituted with 0-2 R1 substituents;
(d) naphthyl, which is independently substituted with 0-2 R1 substituents;and (e) a monocyclic or fused bicyclic heterocyclic ring system having from 5 to ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R1 substituents;
R1 is selected from:
Halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl,-CN, -NO2, (CH2)m NR2R3, SO2NR2R3, SO2R2, CF3, OR2, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, C1-C4 alkyl, -CN C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl and -NO2;
R2 and R3 are independently selected from the group consisting of:
H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN, and -NO2;
m is an integer of 0-2;
Y is a member selected from the group consisting of:
a direct link, -C(=O)-, -N(R4)-, -C(=O)-N(R4)-, -N(R4)-C(=O)-, -SO2 , -O-, -SO2-N(R4)- and -N(R4)-SO2 ;
R4 is selected from:
H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN, and -NO2;.
D is a direct link or is a member selected from the group consisting of:
(a) phenyl, which is independently substituted with 0-2 R1a substituents;
(b) naphthyl, which is independently substituted with 0-2 R1a substituents;
and (c) a monocyclic or fused bicyclic heterocyclic ring system having from 5 to ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R1a substituents;
R1a is selected from:
Halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN, -NO2, (CH2)m NR2a R3a, SO2NR2a R3a, SO2R2a, CF3, OR2a, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN and -NO2.
R2a and R3a are independently selected from the group consisting of:
H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN and -NO2;.
E is a member selected from the group consisting of:
-N(R5)-C(=O)-, -C(=O)-N(R5)-, -N(R5)-C(=O)-N(R6)-, -SO2-N(R5)-, -N(R5)-SO2-N(R6)- and -N(R5)-SO2-N(R6)-C(=O)-;
R5 and R6 are independently selected from:
H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl, C0-4alkylnaphthyl, C0-4alkylheteroaryl, C1-4alkylCOOH and C1-4alkylCOOC1-4alkyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl, naphthyl and heteroaryl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN and -NO2;
G is selected from:
-CR7R8- and -CR7R8a-CR7b R8b-wherein R7, R8, R7a, R8a, R7b and R8b are independently a member selected from from the group consisting of:
hydrogen, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkyl-C3-8cycloalkyl, C0-4alkylphenyl, C0-4alkylnaphthyl, -OR9,-C0-4alkylCOOR9, -C0-4alkylC(=O)NR9R10, -C0-4alkylC(=O)NR9-CH2 CH2 O-R10, -C0-4alkylC(=O)NR9(-CH2-CH2 O-R10-)2, -N(R9)COR10, -N(R9)C(=O)R10, -N(R9)SO2R10, and a naturally occurring or synthetic amino acid side chain, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkyl-C3-8cycloalkyl, -CN and -NO2;
R9 and R10 are independently selected from:
H, C1-4alkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkyl-C3-8cycloalkyl, -CN and -NO2, and wherein R9 and R10 taken together can form a 5-8 membered heterocylic ring;
J is a member selected from the group consisting of:
a direct link, -CH(R11)- and -CH(R11)-CH2-;
R11 is a member selected from the group consisting of:
hydrogen, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkyl-C3-8cycloalkyl, C0-4,alkylphenyl, C0-4alkylnaphthyl, C0-4alkylheterocyclic ring having from 1 to 4 hetero ring atoms selected from the group consisting of N, O and S, CH2COOC1-4alkyl, CH2COOC1-4alkylphenyl and CH2COOC1-4alkylnaphthyl;
Z is a member selected from the group consisting of:
(a) phenyl, which is independently substituted with 0-2 R1b substituents;
(b) naphthyl, which is independently substituted with 0-2 R1b substituents;
and (c) a monocyclic or fused bicyclic heterocyclic ring system having from 5 to ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R1b substituents;
R1b is selected from:
Halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN, -NO2, NR2bR3b, SO2NR2bR3b, SO2R2b, CF3, OR2b, O-CH2-CH2-OR2b, O-CH2-COOR2b, N(R2b)-CH2-CH2-OR2b, N(-CH2-CH2-OR2b)2, N(R2b)-C(=O)R3b, N(R2b)-SO2-R3b, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN and -NO2;
R2b and R3b are independently selected from the group consisting of:
H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN and -NO2;
L is selected from:
H, -CN, C(=O)NR12R13, (CH2)nNR12R13, C(=NR12)NR12R13, OR12, -NR12C(=NR12)NR12R13, and NR12C(=NR12)-R13;
R12 and R13 are independently selected from:
hydrogen, -OR14, -NR14R15, C1-4alkyl, C0-4alkylphenyl, C0-4alkylnaphthyl, COOC1-4alkyl, COO-C0-4alkylphenyl and COO-C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN, and -NO2;
R14 and R15 are independently selected from:
H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC38cycloalkyl, -CN, and -NO2;
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
A is selected from:
(a) C1-C6 alkyl;
(b) C3-C8-cycloalkyl;
(c) phenyl, which is independently substituted with 0-2 R1 substituents;
(d) naphthyl, which is independently substituted with 0-2 R1 substituents;and (e) a monocyclic or fused bicyclic heterocyclic ring system having from 5 to ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R1 substituents;
R1 is selected from:
Halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl,-CN, -NO2, (CH2)m NR2R3, SO2NR2R3, SO2R2, CF3, OR2, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, C1-C4 alkyl, -CN C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl and -NO2;
R2 and R3 are independently selected from the group consisting of:
H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN, and -NO2;
m is an integer of 0-2;
Y is a member selected from the group consisting of:
a direct link, -C(=O)-, -N(R4)-, -C(=O)-N(R4)-, -N(R4)-C(=O)-, -SO2 , -O-, -SO2-N(R4)- and -N(R4)-SO2 ;
R4 is selected from:
H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN, and -NO2;.
D is a direct link or is a member selected from the group consisting of:
(a) phenyl, which is independently substituted with 0-2 R1a substituents;
(b) naphthyl, which is independently substituted with 0-2 R1a substituents;
and (c) a monocyclic or fused bicyclic heterocyclic ring system having from 5 to ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R1a substituents;
R1a is selected from:
Halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN, -NO2, (CH2)m NR2a R3a, SO2NR2a R3a, SO2R2a, CF3, OR2a, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN and -NO2.
R2a and R3a are independently selected from the group consisting of:
H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN and -NO2;.
E is a member selected from the group consisting of:
-N(R5)-C(=O)-, -C(=O)-N(R5)-, -N(R5)-C(=O)-N(R6)-, -SO2-N(R5)-, -N(R5)-SO2-N(R6)- and -N(R5)-SO2-N(R6)-C(=O)-;
R5 and R6 are independently selected from:
H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl, C0-4alkylnaphthyl, C0-4alkylheteroaryl, C1-4alkylCOOH and C1-4alkylCOOC1-4alkyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl, naphthyl and heteroaryl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN and -NO2;
G is selected from:
-CR7R8- and -CR7R8a-CR7b R8b-wherein R7, R8, R7a, R8a, R7b and R8b are independently a member selected from from the group consisting of:
hydrogen, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkyl-C3-8cycloalkyl, C0-4alkylphenyl, C0-4alkylnaphthyl, -OR9,-C0-4alkylCOOR9, -C0-4alkylC(=O)NR9R10, -C0-4alkylC(=O)NR9-CH2 CH2 O-R10, -C0-4alkylC(=O)NR9(-CH2-CH2 O-R10-)2, -N(R9)COR10, -N(R9)C(=O)R10, -N(R9)SO2R10, and a naturally occurring or synthetic amino acid side chain, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkyl-C3-8cycloalkyl, -CN and -NO2;
R9 and R10 are independently selected from:
H, C1-4alkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkyl-C3-8cycloalkyl, -CN and -NO2, and wherein R9 and R10 taken together can form a 5-8 membered heterocylic ring;
J is a member selected from the group consisting of:
a direct link, -CH(R11)- and -CH(R11)-CH2-;
R11 is a member selected from the group consisting of:
hydrogen, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkyl-C3-8cycloalkyl, C0-4,alkylphenyl, C0-4alkylnaphthyl, C0-4alkylheterocyclic ring having from 1 to 4 hetero ring atoms selected from the group consisting of N, O and S, CH2COOC1-4alkyl, CH2COOC1-4alkylphenyl and CH2COOC1-4alkylnaphthyl;
Z is a member selected from the group consisting of:
(a) phenyl, which is independently substituted with 0-2 R1b substituents;
(b) naphthyl, which is independently substituted with 0-2 R1b substituents;
and (c) a monocyclic or fused bicyclic heterocyclic ring system having from 5 to ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R1b substituents;
R1b is selected from:
Halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN, -NO2, NR2bR3b, SO2NR2bR3b, SO2R2b, CF3, OR2b, O-CH2-CH2-OR2b, O-CH2-COOR2b, N(R2b)-CH2-CH2-OR2b, N(-CH2-CH2-OR2b)2, N(R2b)-C(=O)R3b, N(R2b)-SO2-R3b, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN and -NO2;
R2b and R3b are independently selected from the group consisting of:
H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN and -NO2;
L is selected from:
H, -CN, C(=O)NR12R13, (CH2)nNR12R13, C(=NR12)NR12R13, OR12, -NR12C(=NR12)NR12R13, and NR12C(=NR12)-R13;
R12 and R13 are independently selected from:
hydrogen, -OR14, -NR14R15, C1-4alkyl, C0-4alkylphenyl, C0-4alkylnaphthyl, COOC1-4alkyl, COO-C0-4alkylphenyl and COO-C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN, and -NO2;
R14 and R15 are independently selected from:
H, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, C0-4alkylphenyl and C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC38cycloalkyl, -CN, and -NO2;
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
3. A compound of claim 1, wherein:
A is selected from:
(a) phenyl, which is independently substituted with 0-2 R1 substituents;
(b) naphthyl, which is independently substituted with 0-2 R1 substituents;
and (c) a monocyclic or fused bicyclic heterocyclic ring system having from 5 to ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R1 substituents;
Y is a direct link;
D is a member selected from the group consisting of:
(a) phenyl, which is independently substituted with 0-2 R1a substituents;
(b) naphthyl, which is independently substituted with 0-2 R1a substituents;
and (c) a monocyclic or fused bicyclic heterocyclic ring system having from 5 to ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R1a substituents;
E is a member selected from the group consisting of:
-NH-C(=O)-, and -C(=O)-NH-;
G is -CHR7a-CHR7b-;
J is a direct link;
Z is a member selected from the group consisting of:
(a) phenyl, which is independently substituted with 0-2 R1b substituents;
(b) naphthyl, which is independently substituted with 0-2 R1b substituents;
and (c) a monocyclic or fused bicyclic heterocyclic ring system having from 5 to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R1b substituents;
R1b is selected from:
N(R2b)-C(=O)R3b and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN and -NO2; and L is H.
A is selected from:
(a) phenyl, which is independently substituted with 0-2 R1 substituents;
(b) naphthyl, which is independently substituted with 0-2 R1 substituents;
and (c) a monocyclic or fused bicyclic heterocyclic ring system having from 5 to ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R1 substituents;
Y is a direct link;
D is a member selected from the group consisting of:
(a) phenyl, which is independently substituted with 0-2 R1a substituents;
(b) naphthyl, which is independently substituted with 0-2 R1a substituents;
and (c) a monocyclic or fused bicyclic heterocyclic ring system having from 5 to ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R1a substituents;
E is a member selected from the group consisting of:
-NH-C(=O)-, and -C(=O)-NH-;
G is -CHR7a-CHR7b-;
J is a direct link;
Z is a member selected from the group consisting of:
(a) phenyl, which is independently substituted with 0-2 R1b substituents;
(b) naphthyl, which is independently substituted with 0-2 R1b substituents;
and (c) a monocyclic or fused bicyclic heterocyclic ring system having from 5 to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R1b substituents;
R1b is selected from:
N(R2b)-C(=O)R3b and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, -CN and -NO2; and L is H.
4. A pharmaceutical composition for preventing or treating a condition in a mammal characterized by undesired thrombosis comprising a pharmaceutically acceptable carrier and a compound of claim 1.
5. A pharmaceutical composition for preventing or treating a condition in a mammal characterized by undesired thrombosis comprising a pharmaceutically acceptable carrier and a compound of claim 2.
6. A pharmaceutical composition for preventing or treating a condition in a mammal characterized by undesired thrombosis comprising a pharmaceutically acceptable carrier and a compound of claim 3.
7. A method for preventing or treating a condition in a mammal characterized by undesired thrombosis comprising the step of administering to said mammal a therapeutically effective amount of a compound of claim 1.
8. The method of claim 7, wherein the condition is selected from the group consisting of acute coronary syndrome, myocardial infarction, unstable angina, refractory angina, occlusive coronary thrombus occurring post-thrombolytic therapy or post-coronary angioplasty, a thrombotically mediated cerebrovascular syndrome, embolic stroke, thrombotic stroke, transient ischemic attacks, venous thrombosis, deep venous thrombosis, pulmonary embolus, coagulopathy, disseminated intravascular coagulation, thrombotic thrombocytopenic purpura, thromboangiitis obliterans, thrombotic disease associated with heparin-induced thrombocytopenia, thrombotic complications associated with extracorporeal circulation, thrombotic complications associated with instrumentation such as cardiac or other intravascular catheterization, infra-aortic balloon pump, coronary stent or cardiac valve, and conditions requiring the fitting of prosthetic devices.
9. A method for preventing or treating a condition in a mammal characterized by undesired thrombosis comprising the step of administering to said mammal a therapeutically effective amount of a compound of claim 2.
10. The method of claim 9, wherein the condition is selected from the group consisting of: acute coronary syndrome, myocardial infarction, unstable angina, refractory angina, occlusive coronary thrombus occuring post-thrombolytic therapy or post-coronary angioplasty, a thrombotically mediated cerebrovascular syndrome, embolic stroke, thrombotic stroke, transient ischemic attacks, venous thrombosis, deep venous thrombosis, pulmonary embolus, coagulopathy, disseminated intravascular coagulation, thrombotic thrombocytopenic purpura, thromboangiitis obliterans, thrombotic disease associated with heparin-induced thrombocytopenia, thrombotic complications associated with extracorporeal circulation, thrombotic complications associated with instrumentation such as cardiac or other intravascular catheterization, intra-aortic balloon pump, coronary stent or cardiac valve, and conditions requiring the fitting of prosthetic devices.
11. A method for preventing or treating a condition in a mammal characterized by undesired thrombosis comprising the step of administering to said mammal a therapeutically effective amount of a compound of claim 3.
12. The method of claim 11, wherein the condition is selected from the group consisting of: acute coronary syndrome, myocardial infarction, unstable angina, refractory angina, occlusive coronary thrombus occurring post-thrombolytic therapy or post-coronary angioplasty, a thrombotically mediated cerebrovascular syndrome, embolic stroke, thrombotic stroke, transient ischemic attacks, venous thrombosis, deep venous thrombosis, pulmonary embolus, coagulopathy, disseminated intravascular coagulation, thrombotic thrombocytopenic purpura, thromboangiitis obliterans, thrombotic disease associated with heparin-induced thrombocytopenia, thrombotic complications associated with extracorporeal circulation, thrombotic complications associated with instrumentation such as cardiac or other intravascular catheterization, infra-aortic balloon pump, coronary stent or cardiac valve, and conditions requiring the fitting of prosthetic devices.
13. A method for inhibiting the coagulation of biological samples, comprising the step of administering a compound of claim 1.
14. A method for inhibiting the coagulation of biological samples, comprising the step of administering a compound of claim 2.
15. A method for inhibiting the coagulation of biological samples, comprising the step of administering a compound of claim 3.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13581999P | 1999-05-24 | 1999-05-24 | |
| US60/135,819 | 1999-05-24 | ||
| PCT/US2000/014194 WO2000071509A1 (en) | 1999-05-24 | 2000-05-24 | INHIBITORS OF FACTOR Xa |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2382751A1 true CA2382751A1 (en) | 2000-11-30 |
Family
ID=22469841
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002382751A Abandoned CA2382751A1 (en) | 1999-05-24 | 2000-05-24 | Inhibitors of factor xa |
| CA002374820A Abandoned CA2374820A1 (en) | 1999-05-24 | 2000-05-24 | Inhibitors of factor xa |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002374820A Abandoned CA2374820A1 (en) | 1999-05-24 | 2000-05-24 | Inhibitors of factor xa |
Country Status (5)
| Country | Link |
|---|---|
| EP (2) | EP1189879A1 (en) |
| JP (2) | JP2003500387A (en) |
| AU (2) | AU5158100A (en) |
| CA (2) | CA2382751A1 (en) |
| WO (2) | WO2000071509A1 (en) |
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|---|---|---|---|---|
| CN1302292A (en) | 1998-03-19 | 2001-07-04 | 味之素株式会社 | Aminoisoquinoline derivatives |
| DE10008329A1 (en) * | 2000-02-23 | 2001-08-30 | Merck Patent Gmbh | New aminosulfonyl-biphenyl derivatives are Factor Xa and Factor VIIa inhibitors useful e.g. for treating thrombosis, myocardial infarction, arteriosclerosis, inflammation or angina pectoris |
| DE10014645A1 (en) | 2000-03-24 | 2001-09-27 | Merck Patent Gmbh | New amidino-aryl substituted biphenyl derivatives and analogs as Factor Xa inhibitors, are useful for treating thrombosis, myocardial infarction, arteriosclerosis, inflammation, apoplexy or angina pectoris |
| DE10037146A1 (en) * | 2000-07-29 | 2002-02-07 | Merck Patent Gmbh | acetamide derivatives |
| DE10046272A1 (en) * | 2000-09-19 | 2002-03-28 | Merck Patent Gmbh | New biphenyl-substituted amino-(iso)quinoline derivatives, are factor Xa and factor VIIa inhibitors useful e.g. for treating thrombosis, myocardial infarction, inflammation, angina pectoris or restenosis |
| DE10117823A1 (en) * | 2001-04-10 | 2002-10-17 | Merck Patent Gmbh | New N-phenyl-oxalamide derivatives, are factor Xa and factor VIIa inhibitors useful e.g. for treating thrombosis, myocardial infarction, inflammation, angina pectoris or tumor diseases |
| DE10124867A1 (en) * | 2001-05-22 | 2002-11-28 | Boehringer Ingelheim Pharma | New substituted (hetero)aryl-alkenes or -alkynes, used as thrombin inhibitors, serine protease inhibitors, antithrombotic agents and intermediates |
| US7005437B2 (en) | 2001-05-22 | 2006-02-28 | Boehringer Ingelheim Pharma Kg | Substituted aryl and heteroaryl derivatives, the preparation thereof and the use therof as pharmaceutical compositions |
| DE10139060A1 (en) | 2001-08-08 | 2003-02-20 | Merck Patent Gmbh | New bicyclic benzene derivatives useful as factor Xa and VIIa inhibitors, e.g. for treating thrombosis, myocardial infarct, arteriosclerosis, inflammation, stroke, angina, restenosis and tumors |
| AR037097A1 (en) | 2001-10-05 | 2004-10-20 | Novartis Ag | ACILSULFONAMID COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND THE USE OF SUCH COMPOUNDS FOR THE PREPARATION OF A MEDICINAL PRODUCT |
| GB0124939D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124941D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124933D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124934D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| WO2003042190A1 (en) | 2001-11-12 | 2003-05-22 | Pfizer Products Inc. | N-alkyl-adamantyl derivatives as p2x7-receptor antagonists |
| PA8557501A1 (en) | 2001-11-12 | 2003-06-30 | Pfizer Prod Inc | BENZAMIDA, HETEROARILAMIDA AND INVESTED AMIDAS |
| DK1474395T3 (en) | 2002-02-12 | 2008-02-11 | Smithkline Beecham Corp | Nicotinamide derivatives useful as p38 inhibitors |
| DE10214832A1 (en) * | 2002-04-04 | 2003-10-16 | Merck Patent Gmbh | Phenyl derivatives 4 |
| PT1569912E (en) | 2002-12-03 | 2015-09-15 | Pharmacyclics Llc | 2-(2-hydroxybiphenyl-3-yl)-1h-benzoimidazole-5-carboxamidine derivatives as factor viia inhibitors |
| PE20040804A1 (en) | 2002-12-19 | 2004-12-31 | Boehringer Ingelheim Pharma | CARBOXAMID DERIVATIVES AS INHIBITORS OF THE Xa FACTOR |
| US7071223B1 (en) | 2002-12-31 | 2006-07-04 | Pfizer, Inc. | Benzamide inhibitors of the P2X7 receptor |
| PA8591801A1 (en) | 2002-12-31 | 2004-07-26 | Pfizer Prod Inc | BENZAMID INHIBITORS OF THE P2X7 RECEIVER. |
| GB0308186D0 (en) | 2003-04-09 | 2003-05-14 | Smithkline Beecham Corp | Novel compounds |
| GB0308201D0 (en) | 2003-04-09 | 2003-05-14 | Smithkline Beecham Corp | Novel compounds |
| ES2281801T3 (en) | 2003-05-12 | 2007-10-01 | Pfizer Products Inc. | BENZAMIDE INHIBITORS OF THE P2X7 RECEIVER. |
| GB0318814D0 (en) | 2003-08-11 | 2003-09-10 | Smithkline Beecham Corp | Novel compounds |
| US7371743B2 (en) | 2004-02-28 | 2008-05-13 | Boehringer Ingelheim International Gmbh | Carboxylic acid amides, the preparation thereof and their use as medicaments |
| US7550487B2 (en) * | 2004-03-26 | 2009-06-23 | Hoffmann-La Roche Inc. | Pyrrolidine-3,4-dicarboxamide derivatives |
| US7429604B2 (en) | 2004-06-15 | 2008-09-30 | Bristol Myers Squibb Company | Six-membered heterocycles useful as serine protease inhibitors |
| AU2005258911A1 (en) | 2004-06-29 | 2006-01-12 | Pfizer Products Inc. | Method for preparing 5-`4-(2-hydroxy-propyl)-3,5-dioxo-4,5-dihydro-3H`1,2,4!triazin-2-YL!-benzamide derivatives by deprotecting the hydroxyl-protected precursers |
| US7662824B2 (en) | 2005-03-18 | 2010-02-16 | Janssen Pharmaceutica Nv | Acylhydrazones as kinase modulators |
| ATE509925T1 (en) | 2006-11-17 | 2011-06-15 | Pfizer | SUBSTITUTED BICYCLOCARBONIC ACID AMIDE COMPOUNDS |
| EP2590951B1 (en) | 2010-07-09 | 2015-01-07 | Pfizer Limited | Benzenesulfonamides useful as sodium channel inhibitors |
| CN104693093A (en) * | 2015-02-13 | 2015-06-10 | 佛山市赛维斯医药科技有限公司 | Bishydrazide FXa inhibitor and preparation method and use thereof |
| CN104693101A (en) * | 2015-02-13 | 2015-06-10 | 佛山市赛维斯医药科技有限公司 | Bishydrazide derivative as well as preparation method and use thereof |
| CN104693097A (en) * | 2015-02-13 | 2015-06-10 | 佛山市赛维斯医药科技有限公司 | Bishydrazide and alkoxy-naphthyl structure containing compound as well as preparation method and use thereof |
| CN104693095A (en) * | 2015-02-13 | 2015-06-10 | 佛山市赛维斯医药科技有限公司 | Bishydrazide FXa inhibitor and use thereof |
| CN104710341A (en) * | 2015-02-13 | 2015-06-17 | 佛山市赛维斯医药科技有限公司 | Compound containing bishydrazide and naphthyl structure, as well as preparation method and application of compound |
| CN104693096A (en) * | 2015-02-13 | 2015-06-10 | 佛山市赛维斯医药科技有限公司 | Bishydrazide and naphthyl structure containing compound as well as preparation method and use thereof |
| CN104693099A (en) * | 2015-02-13 | 2015-06-10 | 佛山市赛维斯医药科技有限公司 | Bishydrazide and naphthyl structure containing compound and use thereof |
| CN104693102A (en) * | 2015-02-13 | 2015-06-10 | 佛山市赛维斯医药科技有限公司 | Bishydrazide compound as well as preparation method and use thereof |
| CN108976150B (en) * | 2017-06-05 | 2022-11-18 | 重庆博腾制药科技股份有限公司 | Preparation method of 3-ethyl-4-fluorobenzonitrile |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ333696A (en) * | 1996-07-08 | 2000-06-23 | Du Pont Pharm Co | Amidinoindoles, amidinoazoles, and analogs thereof as inhibitors of trypsin like protease enzymes like thrombin and Xa factor |
| US5886191A (en) * | 1997-08-18 | 1999-03-23 | Dupont Pharmaceuticals Company | Amidinoindoles, amidinoazoles, and analogs thereof |
-
2000
- 2000-05-24 JP JP2000619769A patent/JP2003500387A/en active Pending
- 2000-05-24 JP JP2000619766A patent/JP2003500384A/en active Pending
- 2000-05-24 WO PCT/US2000/014194 patent/WO2000071509A1/en not_active Application Discontinuation
- 2000-05-24 AU AU51581/00A patent/AU5158100A/en not_active Abandoned
- 2000-05-24 AU AU52837/00A patent/AU5283700A/en not_active Abandoned
- 2000-05-24 WO PCT/US2000/014207 patent/WO2000071512A1/en not_active Application Discontinuation
- 2000-05-24 CA CA002382751A patent/CA2382751A1/en not_active Abandoned
- 2000-05-24 EP EP00936235A patent/EP1189879A1/en not_active Withdrawn
- 2000-05-24 CA CA002374820A patent/CA2374820A1/en not_active Abandoned
- 2000-05-24 EP EP00937699A patent/EP1183234A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| AU5158100A (en) | 2000-12-12 |
| WO2000071509A1 (en) | 2000-11-30 |
| JP2003500387A (en) | 2003-01-07 |
| CA2374820A1 (en) | 2000-11-30 |
| EP1183234A1 (en) | 2002-03-06 |
| AU5283700A (en) | 2000-12-12 |
| EP1189879A1 (en) | 2002-03-27 |
| JP2003500384A (en) | 2003-01-07 |
| WO2000071512A1 (en) | 2000-11-30 |
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