CZ20002612A3 - Compound, pharmaceutical preparation, use of the compound, method of suppressing immune response, method of therapy and prevention of allergic diseases - Google Patents

Abstract

A compound of formula I wherein rings A, B, and C are independently substituted five or six members heterocycles which can be fused to a benzene ring. W1, W 2 and / or W 3 represent bonds when rings A, B and / or C five-membered heterocycle is substituted, X is -O-, -NR 1, where R1 has a specific meaning, Y has a specific meaning, one V1 and V2 is a bond and the other has the specific meaning of a a pharmaceutical composition containing the same. Use a compound-containing pharmaceutical composition of formula (I) for the treatment and prevention of allergic diseases and to suppress the immune response.

Description

The compound, the pharmaceutical composition, the use of the compound, the method of suppressing the immune response, the method of treating and preventing allergic diseases

Technical field

The present invention relates to a novel tricyclic compound and a pharmaceutical composition for suppressing an immune response, an antiallergic agent or an IgE suppressant composition comprising the compound.

BACKGROUND OF THE INVENTION

Serious problems in tissue or organ transplantation, which is currently frequently performed, are the healing phenomenon that leads to the detachment of the transplanted part after surgery. Preventing tissue rejection is very important for transplant success.

Various immunological response suppressants have been developed, such as azathioprine, corticoid, cyclosporin A, Tacrolimus and the like, and are used in practice to prevent and treat the symptoms of healing in organ or tissue transplantation or in graft versus host disease caused by bone marrow transplantation. However, these compositions are not satisfactory in terms of their effect and side effects.

Allergic diseases, such as atopic dermatitis, allergic rhinitis, bronchial asthma, allergic conjunctivitis and the like, have tended to become widespread in recent years and have become a serious problem. Common anti-inflammatory agents are agents suppressing the release of chemical mediators from mast cells, receptor inhibitors of released chemical mediators, agents suppressing the allergic inflammatory response or the like. All of these are means for symptomatic treatment and there are no essential remedies for allergic diseases.

Therefore, the development of more effective and safer medicines was expected.

Compounds having a similar structure to the compound of the present invention and having an immunosuppressive or antiallergic effect are described in VWO94 / 27980, WO95 / 13067, WO96 / 40659, WO96 / 40143, WO96 / 38412, WO97243560, WO97 / 24324 , WO97 / 46524, JP-A- 8-3163, JP-A- 9-12457, JP-A- 971564, JP-A- 9-124571 and the like. Liquid crystal forming compounds are disclosed in JP-A- 9-87253, JP-A- 63-253065, JP-A-1-106864, JP-A-1-106871, JP-A-2. · ······························ ·

83346, JP-A- 9-48760, JP-A- 9-31063 and the like, compounds exhibiting insecticidal and acrylic activity are disclosed in JP-A- 8-193067 and compounds having therapeutic effects on the circulatory system or psychopathic diseases, are described in EP0600717 A1, all of which have a structure similar to the compound of the present invention.

SUMMARY OF THE INVENTION

The present invention provides a compound of formula I:

wherein rings A, B and C are each independently of each other an optionally substituted aromatic carbon ring or an optionally substituted five or six membered heterocycle which may be fused to a benzene ring,

W ¹ , W ² or represent a bond when ring A, ring B or ring C is an optionally substituted 5-membered heterocycle,

X is -O-, -CH ² -, NR ¹ - wherein R ¹ is hydrogen, optionally substituted lower alkyl, lower alkenyl, lower alkylcarbonyl or optionally substituted lower alkoxycarbonyl or -S (O) p - wherein p is an integer ranging from 0 to 2,

Y is hydrogen, optionally substituted lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkynyl, optionally substituted acyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted lower alkoxycarbonyl, optionally substituted sulfamoyl, optionally substituted amino, optionally substituted aryl or optionally substituted five or six membered heterocycle,

Y is optionally substituted lower alkoxy when X is -CH 2 -,

Y is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl, or optionally substituted arylsulfonyl when X is -O- or -NR ¹ -, one of V ¹ and V ² is a bond and the other is a bond, -Ο-, -NH-, -0CH ₂ -, -CH ₂ O-, -CH = CH-, -C ^ C-, 3 · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · ·

CH (OR ² ) - wherein R ² is hydrogen or lower alkyl, -CO- or -NHCHR 6 - wherein is hydrogen or hydroxyl, and at least one of rings A, B and C is an optionally substituted aromatic carbon ring and at least one other is an optionally substituted 5 or 6 membered heterocycle which can be fused to a benzene ring when both V ¹ and V ² are single bonds, a pharmaceutically acceptable salt thereof, or a hydrate thereof.

The present invention provides a pharmaceutical composition for use as an immunological response suppressing agent, an antiallergic agent, or an IgE suppressing agent comprising Compound I, a pharmaceutically acceptable salt or hydrate thereof.

In one embodiment, the present invention provides a method of suppressing an immune response or a method of treating or preventing allergic diseases, comprising administering Compound I. In another embodiment, the present invention provides the use of Compound I for the manufacture of medicaments

In the present description, the term "halogen" includes fluorine, chlorine, bromine and iodine. Fluorine or chlorine is preferred.

The term "lower alkyl" includes an unbranched or branched alkyl chain containing 1 to 10 carbon atoms, preferably 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms, and most preferably 1 to 3 carbon atoms. Included are, for example, methyl, ethyl, n-propyl, hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, ndecyl and the like.

Examples of substituents of "optionally substituted lower alkyl" are halogen; hydroxyl; lower alkoxy optionally substituted with lower alkoxy; acyl; acyloxy; carboxyl; lower alkoxycarboxyl; mercaptol; lower alkylthiol; amino optionally substituted with hydroxyl, lower alkyl or optionally substituted acyl; an amino group optionally substituted with hydroxyl, lower alkoxy, carboxyl with lower alkoxy, or a 5- or 6-membered heterocycle; a hydrazone group optionally substituted by carbamoyl or lower alkoxycarbonyl; carbamoyl optionally substituted with lower alkyl or amino; thiocarbamoyl optionally substituted with lower alkyl; cycloalkyl optionally substituted with lower alkyl or lower alkoxy, cycloalkenyl optionally substituted with lower alkyl; cyano; phenyl optionally substituted with at least one substituent from the group ·· ·· ·······

hydroxyl, lower alkyl, carboxyl, lower alkoxycarbonyl and lower alkoxy; a five or six membered heterocycle which may be substituted with a lower alkyl and may be fused to a benzene ring; etc. The lower alkyl may be substituted with one or more of these substituents at any possible positions. Preferred are halogen; hydroxyl; acyloxy; phenyl optionally substituted with lower alkyl or lower alkoxy; pyridyl or the like.

The lower alkyl portion of the "lower alkoxy" is the same as the above "lower alkyl".

As examples of substituents for "optionally substituted lower alkoxy" are halogen; hydroxyl; lower alkoxy optionally substituted with lower acyloxy; acyl; acyloxy optionally substituted with hydroxyl or carboxyl; carboxyl; lower alkoxycarboxyl; lower alkylthiol; amino optionally substituted with lower alkyl; phenyl optionally substituted with lower alkyl or lower alkoxy; heterocycle; heterocyclylcarbonyloxy and the like.

The portions of the lower alkyl in "lower alkoxycarbonyl", "lower alkylsulfonyl", "lower alkylsulfonyloxy", "lower alkylthionyl", "lower aminoalkyl" and "lower alkylenedioxyl" are the same as the above "lower alkyl". The substituents for "optionally substituted lower alkylcarbonyl", "optionally substituted lower alkylsulfonyl" and "optionally substituted lower alkylthionyl" are the same as for the above "optionally substituted lower alkoxy".

The term "lower alkenyl" includes an unbranched or branched alkenyl chain containing 2 to 10 carbon atoms, preferably 2 to 8 carbon atoms, more preferably 3 to 6 carbon atoms, having at least one double bond at any possible position. Included are, for example, vinyl, propenyl such as 2-propenyl and the like, isopropenyl, butenyl, isobutenyl, prenyl, butadienyl, pentenyl, isopentenyl, pentadienyl, hexenyl, isohexenyl, hexadienyl, heptenyl, octenyl, nonenyl, decenyl and the like. The substituents for the "optionally substituted lower alkenyl" are the same as for the above-mentioned "optionally substituted lower alkoxy" and preference is given to halogen-substituted alkenyl or unsubstituted alkenyl.

The parts of the lower alkenyl in "lower alkenyloxy", "lower alkenyloxycarbonyl" and "lower aminoalkenyl" are the same as the above-mentioned "lower alkenyl". The substituents for "optionally substituted lower alkenyloxy", "optionally substituted lower alkenyloxycarbonyl" and "optionally substituted lower alkenylthionyl" are the same as for the above "optionally substituted lower alkoxy".

• 9 9 99 99 9 9 9 9 9 9 9 99 99 99 99

The term "lower alkynyl" includes an unbranched or branched alkynyl chain containing 2 to 10 carbon atoms, more preferably 2 to 8 carbon atoms and even more preferably 3 to 6 carbon atoms, and is represented by ethynyl, propynyl such as 2propinyl, butynyl such as 2-butynyl , pentinyl, hexinyl, heptinyl, octinyl, noninyl, decinyl and the like. These have at least one triple bond and may have some double bonds at any possible positions. The substituents for "optionally substituted lower alkynyl" are the same as for the above "optionally substituted lower alkoxy".

The term "acyl" includes straight or branched aliphatic acyl having 1 to 20 carbon atoms, more preferably 1 to 15 carbon atoms, even more preferably 1 to 8 carbon atoms, even more preferably 1 to 6 carbon atoms, and most preferably 1 to 4 carbon atoms, a cyclic aliphatic acyl having 4 to 9 carbon atoms, more preferably 4 to 7 carbon atoms, and aroyl. Included are, for example, formyl, acetyl, propionyl, bytryl, isobutyryl, valeryl, pivaloyl, hexanoyl, acryloyl, propioloyl, methacryloyl, crotonoyl, cyclopropylcarbonyl, cyclohexylcarbonyl, cyclooctylcarbonyl, benzoyl and the like. The substituents for "optionally substituted acyl" are the same as for the above-mentioned "optionally substituted lower alkoxy" and the aroyl can be further substituted with lower alkyl. Among the substituents, halogen is preferred.

The acyl moiety in "acyloxy" is the same as the above "acyl" and the substituents for "optionally substituted acyloxy" are the same as for the above "optionally substituted acyl".

The term "lower alkylcarbonyl" includes an aliphatic acyl having 2 to 4 carbon atoms and includes acetyl, propyl, butyryl, isobutyryl and the like. Acetyl is preferred.

The term "cycloalkyl" includes carbon cycles having 3 to 6 carbon atoms and cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. As examples of substituents for "optionally substituted cycloalkyl" are lower alkyl, halogen, hydroxyl, carboxyl, lower alkoxycarboxyl, lower alkoxy, lower alkylenedioxyl, imino optionally substituted by lower alkoxy, aryl, five or six membered heterocycle and the like and the cycloalkyl may be substituted in any suitable position.

The term "cycloalkenyl" includes a group that has at least one double bond at any suitable position in the above cycloalkyl and is represented by cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, and the like.

404 »40 0 4440

4 4 40 0 0404 ··· · 00 00 00 00 · 00 0400

44000 04 0 40 4-cyclohexanedienyl and the like. The substituents for "optionally substituted cycloalkenyl" are the same as for the above-mentioned "cycloalkyl".

By way of example, the substituents for the "optionally substituted amino" are optionally substituted lower alkyl {wherein the substituents are lower alkoxy, cycloalkyl, optionally substituted amino (where the substituents are aroyl optionally substituted with lower acyloxyalkoxy), optionally substituted aryl (where substituents are lower alkyl, lower alkoxy, carboxyl or lower alkoxycarbonyl) or heterocycle}; lower alkenyl; lower alkynyl; cycloalkyl; aryl optionally substituted with lower alkyl, carboxyl, acyl, lower alkoxycarbonyl; sulfamoyl optionally substituted with lower alkyl; optionally substituted lower alkoxycarbonyl (wherein the substituents are halogen, acyloxy, acyloxy substituted by hydroxyl, acyloxy substituted by carboxyl or heterocyclylcarbonyloxy or the like); lower alkysulfonyl and the like.

The term "optionally substituted carbamoyl" includes carbamoyl optionally substituted with lower alkyl, lower alkenyl; lower alkynyl or the like.

The term "optionally substituted sulfamoyl" includes sulfamoyl optionally substituted with lower alkyl, lower alkenyl; lower alkynyl or the like.

The term "aromatic carbon cycle" includes a benzene ring, a naphthalene ring, anthracene ring, a phenanthrene ring, an indene ring and the like, a benzene ring being preferred.

The term "aryl" includes phenyl, naphthyl, anthryl, phenanthryl, indenyl and the like, and phenyl is preferred.

As examples of substituents for the "optionally substituted aromatic carbon ring" and "optionally substituted aryl" are halogen; hydroxyl; lower alkyl optionally substituted by halogen or carboxyl; lower alkoxy optionally substituted by halogen, aryl, heteroaryl or lower alkoxy; lower alkenyl; lower alkynyl; cycloalkyl; lower alkenyloxy; lower alkynyloxy; cycloalkoxyl; acyl; acyloxy; carboxyl; lower alkoxycarbonyl; lower alkenyloxycarbonyl; lower alkylthionyl; lower alkynylthionyl; amino optionally substituted with lower alkyl, lower cycloalkylalkyl, lower heteroarylalkyl, lower alkenyl, cycloalkyl, aryl optionally substituted with halogen, lower alkoxycarbonyl or lower alkylsulfonyl; guanidine; nitro; lower alkylsulfonyl; dihydroxyborane; lower alkylsulfonyloxy optionally substituted with halogen; arylsulfonyl; arylsulfonyloxy; aryl; a five or six membered heterocycle and the like. The aromatic carbon ring and aryl may be 4

9 4

9 4

4 • 4 4 4 * 4 4 4 4 4 4

4 ·· * 4 • 4

These substituents are substituted by one or more of any possible positions. Preferred examples are halogen; hydroxyl; lower alkyl optionally substituted with halogen; lower alkoxy optionally substituted with aryl or lower alkoxy; lower alkenyloxy; acyloxy; lower alkylthionyl; amino optionally substituted with lower alkyl, lower alkenyl, acyl optionally substituted with halogen or lower alkylsulfonyl; nitro; lower alkylsulfonyl; lower alkylsulfonyl optionally substituted with halogen or arylsulfonyloxy.

The aryl moieties in "arylsulfonyl" and "lower arylsulfonyloxy" are the same as the above-mentioned "aryl" and phenol is preferred. The substituents for the "optionally substituted arylsulfonyl" are the same as for the above-mentioned "optionally substituted aryls," and unsubstituted arylsulfonyl is preferred.

The term "5- or 6-membered heterocycle" includes a 5- or 6-membered heterocycle containing at least one heteroatom optionally selected from O, S and N. Examples of heterocycles include an aromatic heterocycle such as pyrrole ring, imidazole ring, pyrazole ring, pyridine ring such as 4-pyridyl , pyridazine ring, pyrimidine ring, pyrazine ring, triazole ring, triazine ring, isoxazole ring, oxazole ring, oxadiazole ring, isothiazole ring, thiazole ring, thiadiazole ring, furan ring such as 2-furyl or 3-furyl, thiophene ring such as 3-thienyl and the like, an aliphatic heterocycle such as a tetrahydropyran ring, a dihydropyridine ring such as 1,2-dihydropyridyl, a dihydropyridazine such as 2,3-dihydropyridazine, a dihydropyridine ring such as 1,2-dihydropyrazinyl, a dioxane ring, an oxathiorane ring, a thian ring , pyrrolidine ring, pyrrolidine ring, imidazolidine ring, imidazoline ring, p yrazolidine ring, pyrazoline ring, piperidine ring, piperazine ring, morpholine ring and the like.

The term "5- or 6-membered heterocycle containing one or two heteroatoms" includes aromatic heterocycles such as pyrrole ring, imidazole ring, pyrazole ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, isoxazole ring, oxazole ring, isothiazole ring, thiazole ring a ring, furan ring, thiophene ring or the like and aliphatic heterocycles such as dioxane ring, oxathiorane ring, thian ring, dihydropyridine ring, pyrrolidine ring, pyrrolidine ring, imidazolidine ring, imidazoline ring, pyrazolidine ring, pyrazoline ring, piperidine ring, piperazine ring, a morpholine ring, or a morpholine ring, or a morpholine ring, or a morpholine ring; Similar to the aforementioned "5- or 6-membered heterocycles". Aromatic heterocycles are preferred.

Examples of the term "5- or 6-membered ring fused to the benzene ring" include indole ring, isoindole ring, benzimidazole ring, indazole ring, quinoline ring, phthalazine ring, quinazoline ring, benzisoxazole ring, benzoxazole ring, benzoxadiazole ring, benzothiazole ring, benzothiazole ring, benzothiazole ring benzisothiazole ring, benzofuran ring, benzothiophene ring, benzotriazole ring, isobenzofuran ring, chromene ring, indoline ring, isoindoline ring and the like.

Examples of substituents for the "optionally substituted 5 or 6 membered heterocycle" and "optionally substituted 5 or 6 membered heterocycle that fuses with the benzene ring" are halogen; hydroxyl; lower alkyl optionally substituted by hydroxyl or acyloxy; lower alkoxy optionally substituted by halogen, aryl or a 5- or 6-membered heterocycle; lower alkenyl; lower alkenyloxy; lower alkynyl; lower alkynyloxy; acyloxy; carboxyl; lower alkoxycarbonyl; mercapto; lower alkylthionyl; lower alkenylthionyl; amino, which may be substituted with one or two halogens, optionally substituted with lower alkyl, wherein the substituents are cycloalkyl or a 5- or 6-membered heterocycle, aryl optionally substituted with halogen, lower alkenyl; cycloalkyl or lower alkylsulfonyl; an imino group optionally substituted with lower alkylsulfonyl; nitro; lower alkylsulfonyl; aryl; a 5- or 6-membered heterocycle; oxo; oxide and the like. These substituents may be substituted at one or more of any possible positions.

Examples of substituents for an "optionally substituted five or six membered heterocycle containing one or two heteroatoms" are the same as above. Preferred is a 5- or 6-membered heterocycle, substituted with lower alkyl or fully unsubstituted.

The term "W ¹ , W ² or represents a bond when ring A, ring B or ring

C is an optionally substituted 5-membered heterocycle "means the following: W ¹ represents a bond when ring A is an optionally substituted 5-membered heterocycle, resulting in the resulting V * and X bond positions on ring A being as shown below.

AND

X—

Each after W ³ represents a bond when ring B or ring C is a five membered heterocycle, resulting in the resulting bond positions and are as shown below.

Both X, V ' and ¹ may bind directly to the heteroatom forming ring A, ring B or ring C.

The term "compound I" includes the obtainable and pharmaceutically acceptable salts of each compound. As an example, "pharmaceutically acceptable salts" are salts with an inorganic acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, hydrofluoric acid, hydrobromic acid and the like; organic acid salts such as formic acid, acetic acid, tartaric acid, lactic acid, citric acid, fumaric acid, maleic acid, succinic acid and the like; organic base salts such as ammonia, trimethylammonium, triethylammonium and the like; alkali metal salts such as sodium, potassium and the like; and alkaline earth metal salts such as calcium, magnesium, and the like.

The compound of the invention includes hydrates and all stereoisomers, for example atropisomers, etc.

BEST MODE FOR CARRYING OUT THE INVENTION.

All compounds I have an immunosuppressive effect, an antiallergic effect or suppress IgE production and the following compounds are particularly preferred.

In formula I,

1) a compound wherein ring A is an optionally substituted benzene ring, preferably ring A is an optionally substituted benzene ring (wherein the substituents are halogen, hydroxyl, lower alkyl, lower alkoxy, acyloxy, lower alkylsulfonyl, optionally substituted lower alkylsulfonyloxy (where the substituents are halogen) or arylsulfonyloxy}, more preferably ring A is an optionally substituted benzene ring (wherein the substituents are halogen, hydroxyl, lower alkyl, lower alkoxy or lower alkylsulfonyloxy),

9 ·· 9 9 9 9 9 9 9 9

9 ·· · 9 · 8 ·

99 9 9999

999 99 · 9 9 9 99 9 • 999 9999 · 99 99 99 99

2) a compound wherein ring B is an optionally substituted benzene ring, an optionally substituted pyridine ring, an optionally substituted pyrimidine ring, an optionally substituted pyridazine ring, an optionally substituted pyrazine ring, an optionally substituted thiophene ring, an optionally substituted furan ring, an optionally substituted pyrazole ring, or an optionally substituted an oxazole ring, preferably ring B is an optionally substituted benzene ring (wherein the substituents are halogen, hydroxyl, lower alkyl, lower alkoxy, lower alkenyloxy, lower alkylthionyl, cycloalkoxy, lower alkoxycarbonyl or lower alkylsulfonyioxyl), optionally substituted pyridine ring (wherein the substituents are halogen, hydroxyl, lower alkyl, lower alkoxy, lower alkylthionyl, lower alkenyl, amino, carboxyl or lower alkoxycarbonyl), an optionally substituted pyrimidine ring (wherein the substituents are halogen, optionally substituted lower alkyl (wherein the substituents are hydroxyl or acyloxy), lower alkoxy, lower alkylthionyl, optionally substituted amino (where substituents are lower alkyl), carboxyl or lower alkoxycarbonyl)}, optionally substituted pyridazine ring (where substituents are halogen, hydroxyl, lower alkyl, lower alkoxy, lower alkylthionyl, lower alkenyl, amino, carboxyl, lower alkoxycarbonyl or oxygen), optionally substituted thiophene ring (where substituents are lower alkyl), optionally substituted pyrazole ring (wherein substituents are optionally substituted lower alkyl (where substituents are hydroxyl), lower alkoxy, carboxyl or lower alkoxycarbonyl}, or an optionally substituted oxazole ring (where substituents are lower alkyl), more preferably ring B is an optionally substituted benzene ring (where substituents are hydroxyl, lower alkyl, lower alkoxy or lower alkylsulfonyioxyl), optionally with substituted pyridine ring (where substituents are halogen or lower alkyl), optionally substituted pyrimidine ring (wherein substituents are optionally substituted lower alkyl (where substituents are hydroxyl or lower acyloxy)), lower alkoxy, lower alkylthionyl, optionally substituted amino (where substituents are lower alkyl ), carboxyl or lower alkoxycarbonyl}, an optionally substituted pyrazole ring {wherein the substituents are optionally substituted lower alkyl (where the substituents are hydroxyls), lower alkoxy, carboxyl or lower alkoxycarbonyl},

3) a compound wherein ring C is an optionally substituted benzene ring, an optionally substituted pyridine ring, an optionally substituted pyrimidine ring, an optionally substituted pyridazine ring, an optionally substituted pyrazine ring, an optionally substituted isoxazole ring, an optionally substituted pyrazole ring, an optionally substituted benzthiazole ring, an optionally substituted morpholine ring, optionally substituted piperazine ring, optionally substituted imidazole ring, optionally substituted triazole ring, optionally substituted dihydropyridine ring, optionally substituted dihydropyridazine ring or optionally substituted dihydro pyrazine ring, preferably ring C is an optionally substituted benzene ring {wherein the substituents are halogen, hydroxyl, optionally substituted lower alkyl (where the substituents are halogen), optionally substituted lower alkoxy (where the substituents are aryl or lower alkoxy) , lower alkenyloxy, lower alkylthionyl, optionally substituted amino (wherein the substituents are lower alkyl, lower alkenyl, optionally substituted acyl (where the substituents are halogen) or lower alkylsulfonyl), nitro, lower alkylsulfonyl or lower alkylsulfonyloxy}, optionally substituted pyridine ring, optionally substituted a pyrimidine ring, an optionally substituted pyridazine ring, an optionally substituted pyrazine ring, an optionally substituted isoxazole ring, an optionally substituted pyrazole ring (wherein the substituents are halogen, hydroxyl, optionally substituted lower alkyl (wherein the substituents are hydroxyl or acyloxy)), optionally substituted lower alkoxy (wherein substituents are halogen, aryl or a 5- or 6-membered heterocycle), lower alkenyl, lower alkenyloxy, lower alkynyl, lower alkynyloxy, acyloxy, carboxyl, lower alkoxycarbonyl, mercapto, lower alkylthio nyl, lower alkenylthionyl, optionally substituted amino at one or two positions (wherein the substituents are halogen, optionally substituted lower alkyl (wherein the substituents are cycloalkyl or a five or six membered heterocycle), optionally substituted acyl (where the substituents are halogen), lower alkenyl, cycloalkyl or lower alkylsulfonyl}, optionally substituted amino (wherein the substituents are lower alkylsulfonyl}, nitro, lower alkylsulfonyl, aryl, 5- or 6-membered heterocycle, oxo or oxide}, benzothiazole ring, benzothiazole ring, An optionally substituted dihydropyridine ring (wherein the substituents are oxo), an optionally substituted dihydropyridazine ring (a) an optionally substituted dihydropyridine ring (wherein the substituents are oxo); wherein the substituents are oxo), an optionally substituted dihydropyrazine ring (wherein the substituents are oxo), more preferably is k ruh C an optionally substituted benzene ring {wherein the substituents are halogen, hydroxyl, optionally substituted lower alkyl (where the substituents are halogen), optionally substituted lower alkoxy (where the substituents are aryl), lower alkenyloxy, lower alkylthionyl, optionally substituted amino at one or two positions {wherein the substituents are lower alkyl, lower alkenyl, optionally substituted acyl (where substituents are halogen) or lower alkylsulfonyl], nitro, lower alkylsulfonyl or lower alkylsulfonyloxy}, optionally substituted pyridine ring {wherein substituents are halogen, hydroxyl, lower alkyl, lower alkenyl , lower alkynyl, optionally substituted lower alkoxy (wherein the substituents are halogen, aryl or a 5- or 6-membered heterocycle), lower alkenyloxy, lower alkynyloxy, lower alkylthionyl, lower alkenylthionyl, optionally substituted amino (wherein the substituents are ni (lower alkyl, heterocyclyl (lower) alkyl, cycloalkylalkyl, lower alkenyl or cycloalkyl), lower alkylsulfonyl, 5- or 6-membered heterocycle, nitro or oxo}, optionally substituted pyrimidine ring {wherein the substituents are halogen, hydroxyl, optionally substituted lower alkoxy (wherein the substituents are aryl), lower alkenyloxy or optionally substituted amino (where substituents are lower alkyl or lower alkenyl)}, optionally substituted pyridazine ring {where substituents are halogen, optionally substituted lower alkoxy (where substituents are aryl), lower alkenyloxy or optionally substituted amino (where substituents are lower alkyl, lower alkoxy or lower alkenyl)}, an optionally substituted pyrazine ring {wherein the substituents are halogen, optionally substituted lower alkoxy (where the substituents are aryl), lower alkenyloxy or an optionally substituted amino group (wherein the substituents are the substituents are lower alkenyl)},

4) a compound wherein X is -O- or -NR ¹ - (wherein R ¹ is hydrogen, methyl or prenyl), preferably is X-Ο-, -NH- or -NMe-, more preferably X is -O- or -NH- ,

5) a compound wherein Y is hydrogen, optionally substituted lower alkyl, optionally substituted lower alkenyl, lower alkylsulfonyl, or optionally substituted acyl, preferably Y is optionally substituted lower alkyl, optionally substituted lower alkenyl, lower alkylsulfonyl, or optionally substituted acyl, more preferably Y is optionally substituted lower alkyl {wherein the substituents are a 5- or 6-membered heterocycle or optionally substituted phenyl (where the substituents are lower alkyl or lower alkoxy)} or optionally substituted lower alkenyl (where the substituents are halogen), most preferably Y is methyl, optionally substituted prenyl (wherein the substituents are halogen) or optionally substituted benzyl (wherein the substituents are lower alkyl or lower alkoxy),

6) a compound wherein X is -O- or -NH- and Y is optionally substituted prenyl (where substituents are halogen) or optionally substituted benzyl (wherein substituents are lower alkyl or lower alkoxy), or X is -NR ¹ and Y is methyl, preferably -XY -OCH ₂ CH = CMe ₂ , OBn, -OCH ₂ C ₆ H ₄ -2-Me, -OCH ₂ C ₆ H ₄ -3-Me, OCH ₂ C ₆ H ₄ -4-Me , -OCH ₂ C ₆ H ₄ -4-OMe, -NMe ₂ or -NHCH ₂ CH = CMe ₂ , more preferably -XY -OCH ₂ CH = CMe ₂ , OBn or -NMe ₂ ,

7) a compound wherein one of V ¹ and V ² is a single bond and the other is a single bond, -O- or -NH-, preferably V ^{1 is a} single bond and V ² is a single bond, -O- or -NH-, even more preferably, both V ¹ and V ² are single bonds,

8) a compound wherein ring A is an optionally substituted benzene ring, ring B is an optionally substituted benzene ring, an optionally substituted pyridine ring, an optionally substituted pyrimidine ring, an optionally substituted pyridazine ring, an optionally substituted pyrazine ring, an optionally substituted thiophene ring, an optionally substituted furan ring , optionally substituted pyrazole ring or optionally substituted oxazole ring, ring C is an optionally substituted benzene ring, optionally substituted pyridine ring, optionally substituted pyrimidine ring, optionally substituted pyridazine ring, optionally substituted pyrazine ring, optionally substituted isoxazole ring, optionally substituted pyrazole ring, optionally substituted benzothiazole ring, optionally substituted morpholine ring, optionally substituted piperazine ring, optionally substituted imidazole ring or optionally a fused-substituted triazole ring,

X is -O- or -NR ¹ -, wherein R ¹ is hydrogen, methyl or prenyl;

Y is an optionally substituted lower alkyl or an optionally substituted lower alkenyl and one of V ¹ and V ² is a single bond and the other is a single bond, -O- or -NH-, preferably ring A is an optionally substituted benzene ring {wherein the substituents are halogen, hydroxyl, lower alkoxy, acyloxy, lower alkylsulfonyl, optionally substituted alkylsulfonyloxy (where the substituents are halogen) or arylsulfonyloxy}, ring B is an optionally substituted benzene ring (wherein the substituents are halogen, hydroxyl, lower alkyl, lower alkoxy, lower alkoxycarbonyl, lower alkenyloxy or lower alkylsulfonyloxy), optionally substituted pyridine ring (where substituents are halogen or lower alkyl), optionally substituted pyrimidine ring (wherein substituents are optionally substituted lower alkyl (where substituents are hydroxyl or acyloxy)), lower alkoxy, lower alkylthionyl, optionally substituted amino (where the substituents are lower alkyl), carboxyl or alkylsulfonyl, optionally substituted alkylsulfonyloxy (where substituents are halogen) or lower alkoxycarbonyl)}, optionally substituted pyridazine ring (where substituents are lower alkyl or oxide), optionally substituted thiophene ring (where substituents are lower alkyl), optionally substituted pyrazole ring {wherein the substituents are optionally substituted lower alkyl (where the substituents are hydroxyl), lower alkoxy, carboxyl or lower alkoxycarbonyl)}, or an optionally substituted oxazole ring (where the substituents are lower alkyl), ring C is an optionally substituted benzene ring {wherein the substituents are halogen, hydroxyl, optionally substituted lower alkyl (where the substituents are halogen), optionally substituted lower alkoxy (where the substituents are aryl or lower alkoxy), lower alkenyloxy, lower alkylthionyl, optionally substituted amino (wherein the substituents are lower and alkyl, lower alkenyl, optionally substituted acyl (wherein the substituents are halogen) or lower alkylsulfonyloxy}, nitro, lower alkylsulfonyl or alkylsulfonyloxy}, optionally substituted pyridine ring {wherein the substituents are halogen, hydroxyl, optionally substituted lower alkyl, lower alkenyl, lower alkynyl, optionally substituted lower alkoxy (wherein the substituents are halogen, aryl or a 5- or 6-membered heterocycle), lower alkenyloxy, lower alkynyloxy, lower alkylthionyl, lower alkenylthionyl, optionally substituted amino (wherein the substituents are lower alkyl, heterocyclyl)

9 ··

(Lower) alkyl, cycloalkylalkyl, lower alkenyl or cycloalkyl), lower alkylsulfonyl, 5- or 6-membered heterocycle, nitro or oxo}, optionally substituted pyrimidine ring {wherein the substituents are halogen, hydroxyl, optionally substituted lower alkoxy (where the substituents are aryl), lower alkenyloxy or an optionally substituted amino group (where the substituents are lower alkyl or lower alkenyl)}, an optionally substituted pyridazine ring {where the substituents are halogen, optionally substituted lower alkoxy (where the substituents are aryl), lower alkenyloxy or optionally substituted amino (where substituents are lower alkyl, lower alkoxy or lower alkenyl)}, optionally substituted pyrazine ring {wherein substituents are halogen, optionally substituted lower alkoxy (where substituents are aryl), lower alkenyloxy, optionally substituted amino (wherein substituent uents are lower alkenyl)}, optionally substituted isoxazole ring {wherein substituents are optionally substituted lower alkoxy (where substituents are aryl), lower alkenyloxy or optionally substituted amino (wherein substituents are lower alkenyl or lower alkylsulfonyl)}, optionally substituted pyrazole ring {where the substituents are lower alkyl, optionally substituted lower alkoxy (wherein the substituents are aryl), lower alkenyloxy or optionally substituted amino (wherein the substituents are lower alkenyl or lower alkylsulfonyl)}, or a benzothiazole ring,

X is -O-, -NH-, or -NMe-,

Y is optionally substituted lower alkyl {wherein the substituents are a five or six membered heterocycle or optionally substituted phenyl (where the substituents are lower alkyl or lower alkoxy)} or lower alkenyl (where the substituents are halogen), and one is a single bond and the other is a single bond , -O- or -NH-, more preferably Ring A is an optionally substituted benzene ring (wherein substituents are halogen, hydroxyl, lower alkoxy or lower alkylsulfonyloxy), Ring B is a benzene ring (wherein substituents are halogen, hydroxyl, lower alkyl, lower alkoxy or lower alkoxycarbonyl), optionally substituted pyridine ring (where substituents are halogen or lower alkyl), optionally substituted pyrimidine ring (where substituents are optionally substituted lower alkyl (where substituents are hydroxyl or acyloxy)), lower alkoxy, lower ·· ·· · · · · · · · · · · · · · · · · · · · · Alkylthionyl, optionally substituted amino (where substituents are lower alkyl), carboxyl or lower alkoxycarbonyl)}, optionally substituted pyrazole ring {where substituents are optionally substituted lower alkyl (wherein the substituents are hydroxyl), lower alkoxy, carboxyl or lower alkoxycarbonyl)}, ring C is an optionally substituted benzene ring {wherein the substituents are halogen, hydroxyl, optionally substituted lower alkyl (where the substituents are halogen), optionally substituted lower alkoxy ( wherein the substituents are aryl), lower alkenyloxy, lower alkylthionyl, optionally substituted amino {where substituents are lower alkyl, lower alkenyl, optionally substituted acyl (where the substituents are halogen) or lower alkylsulfonyloxy}, nitro, lower alkylsulfonyl or alkylsulfonyloxy}, optionally substituted pyridine ring {wherein the substituents are halogen , hydroxyl, lower alkyl, lower alkenyl, lower alkynyl, optionally substituted lower alkoxy (wherein the substituents are halogen, aryl or a 5- or 6-membered heterocycle), lower alkenyloxy, lower alkynyloxy, lower alkylthionyl, lower alkenylthionyl, optionally substituted amino (wherein the substituents are lower alkyl, lower heterocyclylalkyl, cycloalkylalkyl, lower alkenyl or cycloalkyl), lower alkylsulfonyl, 5- or 6-membered heterocycle, nitro or oxo}, optionally substituted pyrimidine ring (where substituents are halogen, hydroxyl, optionally substituted lower alkoxy (where substituents are aryl), lower alkenyloxy or optionally substituted amino (where substituents are lower alkyl or lower alkenyl)}, optionally substituted pyridazine ring {where substituents are halogen, optionally substituted lower alkoxy (where substituents are aryl), lower alkenylox yl or an optionally substituted amino group (wherein the substituents are lower alkyl, lower alkoxy or lower alkenyl)}, or an optionally substituted pyrazine ring {wherein the substituents are halogen, optionally substituted lower alkoxy (wherein the substituents are aryl), lower alkenyloxy or optionally substituted amino (wherein substituents are lower alkenyl)},

X is -O- and Y is prenyl or optionally substituted benzyl (wherein the substituents are lower alkyl or lower alkoxy) or X is -NR ¹ - and Y is methyl,

V ¹ is a single bond and V ² is a single bond, -O- or -NH-, ftftft ftft ftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftftft More preferably, ring A is an optionally substituted benzene ring (wherein the substituents are halogen, hydroxyl, lower alkoxy or lower alkylsulfonyloxy), ring B is an optionally substituted benzene ring (wherein the substituents are halogen, hydroxyl, lower alkyl, lower alkoxy or lower alkoxycarbonyl), optionally substituted pyridine ring (where substituents are lower alkyl), optionally substituted pyrimidine ring (where substituents are lower alkyl), lower alkoxy, carboxyl or lower alkoxycarbonyl), optionally substituted pyrazole ring (where substituents are lower alkyl, lower alkoxy , carboxyl or lower alkoxycarbonyl), ring C is an optionally substituted benzene ring (wherein the substituents are halogen, hydroxyl, lower alk oxyl, lower alkenyloxy, optionally substituted amino (where substituents are lower alkyl) or lower alkylsulfonyloxy)}, optionally substituted pyridine ring {where substituents are optionally substituted amino groups {where substituents are halogen, lower alkyl, optionally substituted lower alkoxy (where substituents are aryl or a 5- or 6-membered heterocycle), lower alkenyloxy or optionally substituted amino (wherein substituents are lower alkyl, heterocyclyl (lower) alkyl or lower alkenyl)}, optionally substituted pyrimidine ring {wherein substituents are halogen, hydroxyl, lower alkoxy, lower alkenyloxy, amino or a lower alkenylamine), an optionally substituted pyridazine ring (wherein the substituents are halogen, lower alkoxy, lower alkenyloxy, amino, lower alkylamine or lower alkenylamine), or an optionally substituted pyrazine ring (wherein the substituents are lower s alkenyloxy, amino or lower alkenylamine)

X is -O- and Y is prenyl or optionally substituted benzyl (wherein the substituents are lower alkyl or lower alkoxy) or X is -NR 1 - and Y is methyl or prenyl, is a single bond and is a single bond, -O- or -NH -,

9) a compound wherein two of rings A, B or C are optionally substituted benzene rings and the third is an optionally substituted five or six membered heterocycle that fuses with the benzene ring, preferably ring A is an optionally substituted benzene ring, one of rings B and C is an optionally substituted benzene ring and the other is an optionally substituted 5 or 6 membered heterocycle that fuses with the benzene ring,

00

0 0 0

0 0 0

0 0 0

0 0 0

00 • 00 00 0000 00 0 0 4 4 0 • 00000 0 0 0 0 0 0 0 0

Even more preferably, ring A is an optionally substituted benzene ring, one of rings B and C is an optionally substituted benzene ring and the other is an optionally substituted five or six membered heterocycle that fuses to the benzene ring, and both V ¹ and V ² are simple bindings,

10) a compound wherein all rings A, B and C are optionally substituted benzene rings and V ¹ is a single bond and V ² is -O- or -NH-,

11) a compound wherein both rings A and B are optionally substituted benzene rings and XY is -ΝΜβ2, prenyloxy or prenylamine, preferably both rings A and B are optionally substituted benzene rings and ring C is an optionally substituted pyridine ring, an optionally substituted pyrimidine ring, an optionally substituted pyridazine ring, an optionally substituted isoxazole ring, or an optionally substituted pyrazole ring, -XY is -NMe 2, prenyloxy or prenylamine and both V ¹ and V ² are single bonds,

12) compounds having any of the following general formulas

wherein R ⁴ , R ®, R ® and R ⁷ are independently hydrogen, halogen, hydroxyl, lower alkoxy, acyloxy, optionally substituted lower alkylsulfonyloxy (where the substituents are halogen), or arylsulfonyloxy,

R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ are independently hydrogen, hydroxyl, lower alkyl, lower alkoxy or alkylsulfonyloxy,

ΦΦ · φ φ φ φ φ φ φ φ φ φ · · · · · · · · · · · · · · φ φ φ φ φ

R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ independently of one another are hydrogen, halogen, hydroxyl, optionally substituted lower alkyl (where the substituents are halogen), optionally substituted lower alkoxy (where the substituents are aryl), lower alkenyloxy, lower alkylthionyl, lower alkylsulfonyl, lower alkyisulfonyloxy, nitro or optionally substituted amino (where substituents are lower alkyl, lower alkenyl, optionally substituted acyl (where substituents are halogen) or lower alkylsulfonyl}, ring B is an optionally substituted pyridine ring (where substituents are halogen or lower alkyl) , optionally substituted pyrimidine ring {wherein substituents are optionally substituted lower alkyl (where substituents are hydroxyl or acyloxy)), lower alkoxy, lower alkylthionyl, optionally substituted amino (where substituents are lower alkyl), carboxyl or lower alkoxycarbonyl)}, optionally substituted pyridazine ring (to de substituents are lower alkyl or oxide), optionally substituted thiophene ring (where substituents are lower alkyl), optionally substituted pyrazole ring (wherein substituents are optionally substituted lower alkyl (where substituents are hydroxyl), lower alkoxy, carboxyl or lower alkoxycarbonyl)}, or an optionally substituted oxazole ring (where the substituents are lower alkyl), ring C is an optionally substituted pyridine ring (wherein the substituents are hydroxyl, halogen, lower alkyl, optionally substituted lower alkoxy (wherein the substituents are aryl), lower alkenyloxy, optionally substituted amino group {wherein substituents are lower alkyl, optionally substituted acyl (where substituents are halogen), lower alkenyl or lower alkylsulfonyl}, nitro, lower alkylthionyl, lower alkylsulfonyl, or optionally substituted amino (where substituents are lower alkylsulfonyl)}, optionally substituted pyrimidi a new ring {wherein the substituents are halogen, hydroxyl, optionally substituted lower alkoxy (where the substituents are aryl), lower alkenyloxy or an optionally substituted amino group (where the substituents are lower alkyl or lower alkenyl)}, optionally substituted pyridazine ring {wherein the substituents are halogen, optionally substituted lower alkoxy (wherein the substituents are aryl), lower alkenyloxy or optionally substituted amino (wherein the substituents are lower alkyl, lower alkoxy, lower alkenyl or lower alkenyloxy)},

• fcfc Fc fcfcfcfc • ·· • fcfc • • • fcfc · • • fc fcfcfc • · • · · • • • • • · • • · • • • • fcfcfc fcfc fcfc · fcfc fcfc

an optionally substituted pyrazine ring {wherein the substituents are halogen, optionally substituted lower alkoxy (where the substituents are aryl), lower alkenyloxy or an optionally substituted amino group (where the substituents are lower alkyl or lower alkenyl)}, optionally substituted isoxazole ring {wherein the substituents are optionally substituted lower alkoxy (wherein the substituents are aryl), lower alkenyloxy or optionally substituted amino (where substituents are lower alkenyl or lower alkylsulfonyl)}, optionally substituted pyrazole ring {wherein substituents are lower alkyl, optionally substituted lower alkoxy (where substituents are aryl), lower alkenyloxy or an optionally substituted amino group (wherein the substituents are lower alkenyl or lower alkylsulfonyl)}, the benzothiazole ring, the morpholine ring, the piperazine ring (where the substituents are lower alkyl or phenyl), the imidazole ring, or the triazole ring is single bond or -0-

V ² is a single bond, -Ο-, -NH-, -OCH 2 -, -CH 2 O-, -CH = CH-, -CsC-, -CH (OEt) -, CH (OH) -, -CO-, - NHCH ₂ - or -NHCH (OH) -,

X is -O-, -NF 1 - {wherein is halogen, optionally substituted lower alkyl, lower alkenyl, lower alkylcarbonyl, or optionally substituted alkoxycarbonyl), and Y is methyl, optionally substituted prenyl (where the substituents are halogen) or optionally substituted benzyl (wherein substituents are lower alkyl or lower alkoxy)

13) a compound wherein both rings A and B are optionally substituted benzene rings and ring C is

Y is CH 2 CH = CHMe 2 and both V ¹ and V ² are single bonds,

14) a compound wherein both rings A and B are benzene rings, ring C is ftftftftft

X is -Ο-, Y is hydrogen and both V ¹ and V ² are single bonds,

15) a compound wherein both rings A and B are optionally substituted benzene rings, ring C is ftft ftftft ftftft ftft ftftft ftft ftft ftft ftft ftft ftft ftft ftft • ft ftft

HN //

X is -NH- and both V ¹ and V ² are single bonds.

Another preferred embodiment is [1] a compound having the following general formula 1b ':

wherein ring C is an optionally substituted five or six membered heterocycle that contains one or two heteroatoms and represents a bond when ring C is a five membered heterocycle,

X and X 'are each independently -O-, -CH ² -, -NR ¹ - wherein R ¹ is hydrogen, optionally substituted lower alkyl, lower alkenyl, lower alkylcarbonyl, or optionally substituted lower alkoxycarbonyl or -S (O) p - where p is an integer between 0 and 2,

Y and Y 'are each independently optionally substituted lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkynyl, optionally substituted acyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted lower alkoxycarbonyl, optionally substituted amino, optionally substituted sulfamoyl, optionally substituted aryl or optionally substituted 5 or 6 membered heterocycle,

R 1 together with Y and Y 'form - (CH 2) m -, - (CH 2) 2 -Q- (CH 2) 2 - wherein Q is CH 2, O, S or

NR ', -CR' = CH-CH = CR'-, -CH = N-CH = CH-, -N = CH-N = CH-, -C (= O) -O (CH ₂ ) N-, -C (= O) NR '- (CH 2) N- or -C (= O) -NR'-N = CH- wherein m is 4 or 5, n is 2 or 3, R' is hydrogen, lower alkyl or lower alkenyl, • 0 0 0 · 0 00 0 ·· 04 · 0 · 0 0 0 0 0 0

000 04 4 0000 • 04000 00 40 40 0 • 044 0004

000 04 00 0 00 00

Y is optionally substituted lower alkoxy when X is -CH 2 -, Y 'is optionally substituted lower alkoxy when X' is -CH 2 -,

Y is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl, or optionally substituted arylsulfonyl when X is -O- or -NR ¹ -,

Y 'is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl or optionally substituted arylsulfonyl when X' is -O- or -NR ¹ -,

Y is hydrogen or halogen when X is -CH ² - or -NR ¹ -,

Y 'is hydrogen or halogen when X' is -CH ² - or -NR ¹ -.

R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ are independently hydrogen, halogen, hydroxyl, optionally substituted lower alkyl, optionally substituted lower alkoxy, optionally substituted lower alkenyl, optionally substituted lower alkenyloxy, optionally substituted cycloalkyloxy, optionally substituted acyloxy, carboxyl, optionally substituted lower alkoxycarbonyl, optionally substituted lower alkenyloxycarbonyl, optionally substituted lower alkylthionyl, optionally substituted lower alkenylthionyl, optionally substituted amino, optionally substituted carbamoyl, optionally substituted carbamoyl, alkylsulfonyl, optionally substituted lower alkylsulfonyloxy, optionally substituted lower arylsulfonyl or optionally substituted lower arylsulfonyloxy, except for compounds wherein all R ⁸ , R ⁹ , R ¹⁹ and R ¹¹ are hydrogen and halogen.

Among the following compounds of formula Ib ', the following are preferred:

a compound wherein R ⁴ and R ⁸ are each independently hydrogen, hydroxyl, halogen, optionally substituted lower alkyl, optionally substituted lower alkoxy, optionally substituted acyloxy, optionally substituted lower alkylsulfonyloxy or optionally substituted lower arylsulfonyloxy (hereinafter referred to as "R ⁴ and R 8") ⁸ are R45-1 '), a compound wherein R ⁴ and R ⁸ are independently hydrogen, hydroxyl, halogen, lower alkyl, lower alkoxy, acyloxy, optionally substituted lower alkylsulfonyloxy or arylsulfonyloxy (hereinafter referred to as "R ⁴ and R ^8" are R45-2 "), a compound wherein R ⁴ and R ⁸ are independently of each other hydrogen, halogen or lower alkoxy (hereinafter referred to as" R ⁴ and R ⁸ are R 45-3 "), φ» φφφφ «φφ φφ φ · φ φ φ φφφ φ φ »φ φ φφφφ φφφ φφ φφ φ φφ φφ φ φ φ φ φ φ φ · φ φ φ φ φ φ φ φ φ φφ Φ · compounds where one of R ⁴ is hydrogen and the other is halogen (hereinafter referred to as " ^R4 and ^R5 are R45-4 "), a compound wherein one of R ⁴ and R $ is hydrogen and the other is chloro or fluoro (hereinafter referred to as" R ⁴ and R $ are R45-5 "), a compound wherein R ⁴ is hydrogen and R ⁵ is halogen (hereinafter referred to as "R ⁴ and R ⁵ are R456"), a compound wherein R ⁴ is hydrogen and is chlorine or fluorine (hereinafter referred to as "R ⁴ and are R 45-7") , a compound wherein R ® and R ⁷ are independently hydrogen, halogen or lower alkyl (hereinafter referred to as "R ® and R ⁷ are R 67-1"), a compound wherein both R ® and R ⁷ are hydrogen halogen (hereinafter referred to as "R ⁷ ") denoted as "R ⁶ and R ⁷ are R 67-2"), a compound wherein and R 6 are independently hydrogen, halogen, hydroxyl, optionally substituted lower alkyl, optionally substituted lower alkoxy, optionally substituted cycloalkyloxy, optionally substituted lower alkylthionyl, optionally substituted lower alkoxycarbonyl or optionally substituted lower alkylsulfonyloxy (hereinafter referred to as "R ^{8 and} R ¹¹ are R 811-1") , a compound wherein R ⁸ and R 6 are independently hydrogen, halogen, hydroxyl, optionally substituted lower alkyl, optionally substituted lower alkoxy, optionally substituted cycloalkyloxy, optionally substituted lower alkylthionyl, optionally substituted lower alkoxycarbonyl or optionally substituted lower alkylsulfonyloxy (hereinafter referred to as such as "R ^{8 and} R ¹¹ are R 811-2"), a compound wherein R ⁸ and R ⁸ are independently hydrogen, halogen, hydroxyl, optionally substituted lower alkyl, optionally substituted lower alkoxy or optionally substituted lower alkoxycarbonyl (hereinafter referred to as " R 6 and R ⁶ are R 811-3 "), a compound wherein R 6 and R 6 are independently hydrogen, halogen, optionally substituted lower alkyl, optionally substituted lower alkoxy or lower alkoxycarbonyl (hereinafter referred to as" R 6 and R 6 ") ¹¹ are R811-4 “), φφ φφφφ φφ · * φ« φ φ * Φ Φ *

Φ Φ φ «

Φ Φ Φ «

A compound wherein R ⁸ and R ¹¹ are independently hydrogen, optionally substituted lower alkyl, optionally substituted lower alkoxy or lower alkoxycarbonyl (hereinafter referred to as "R ⁸ and R ¹¹ are R 811-5"), the compound wherein R ⁸ and R ¹¹ are independently hydrogen, optionally substituted lower alkyl or optionally substituted lower alkoxy (hereinafter referred to as "R ⁸ and R ¹¹ are R 811-6"), a compound wherein R ⁸ and R ¹¹ are independently optionally substituted lower alkyl or optionally substituted lower alkoxy (hereinafter referred to as "R ⁸ and R ¹¹ are R 8117").

a compound wherein R ⁸ and R ¹¹ are independently lower alkyl or lower alkoxy (hereinafter referred to as "R ⁸ and R ¹¹ are R 811-8"), a compound wherein both R ⁸ and R ¹¹ are optionally substituted lower alkyl or optionally substituted lower alkoxy (hereinafter referred to as "R ⁸ and R ¹¹ are R 811-9"), a compound wherein both R ⁸ and R ¹¹ are lower alkyl or one of R ⁸ and R ¹¹ is lower alkyl and the other is lower alkoxy denoted as "R ⁸ and R ¹¹ are R 811-10"), a compound wherein both R ⁸ and R ¹¹ are lower alkyl (hereinafter referred to as "R ⁸ and R ¹¹ are R 811-11"), a compound wherein R ⁸ and R ¹¹ are each independently methyl or methoxy (hereinafter referred to as "R ⁸ and R ¹¹ are R 811-12"), a compound wherein R ⁹ and R ¹⁸ are independently hydrogen, halogen, hydroxyl, optionally substituted lower alkyl, optionally substituted lower alkoxy, optionally substituted cycloalkyloxy, optionally substituted lower alkylthionyl, optionally substituted lower alkoxycarbonyl or optionally substituted lower alkylsulfonyloxy (hereinafter referred to as "R ^{9 and} R ¹⁸ are R 910-1"), a compound wherein R ⁹ and R ¹⁸ are independently hydrogen, halogen, hydroxyl, optionally substituted lower alkyl, optionally substituted lower alkoxy, cycloalkyloxy, lower alkylthionyl, lower alkoxycarbonyl or optionally substituted lower alkylsulfonyloxy (hereinafter referred to as "R ⁹ and R ¹⁸ are R 910-2"), ·

44 »44 • 4 • 4 • 4 • 4 ee • 4 · 4

A compound wherein R ⁹ and R ¹⁹ independently of one another are hydrogen, halogen, hydroxyl, optionally substituted lower alkyl, optionally substituted lower alkoxy or optionally substituted lower alkylsulfonyloxy (hereinafter referred to as " R ⁹ and R ¹⁹ are R 910-3 "), a compound wherein R ⁹ and R ¹⁹ independently of one another are hydrogen, halogen, hydroxyl, optionally substituted lower alkyl or optionally substituted lower alkoxy (hereinafter referred to as" R ⁹ and R ^{19 ")} R 910-4 "), a compound wherein R ⁹ and R ¹⁹ are independently hydrogen, optionally substituted lower alkyl, or optionally substituted lower alkoxy (hereinafter referred to as" R ⁹ and R ¹⁹ are R 910-5 "), a compound wherein R ⁹ and R ¹⁹ are independently hydrogen or optionally substituted lower alkyl (hereinafter referred to as "R ⁹ and R ¹⁹ are R 910-6"), a compound wherein both R ⁹ and R ¹⁹ are hydrogen or optionally substituted lower alkyl (hereinafter "R ⁹ ") marked j such as "R ⁹ and R ¹⁹ are R 910-7"), a compound wherein both R ⁹ and R ¹⁹ are hydrogen or lower alkyl (hereinafter referred to as "R ⁹ and R ¹⁹ are R 910-8"), a compound wherein both R ⁹ and R ¹⁹ are hydrogen (hereinafter referred to as "R ⁹ and R ¹⁹ are R 9109"), a compound wherein both R ⁹ and R ¹⁹ are lower alkyl (hereinafter referred to as "R ⁹ and R ¹⁹ are R 910-10"), a compound wherein both R ⁹ and R ¹⁹ are independently hydrogen or lower alkyl (hereinafter referred to as "R ⁹ and R ¹⁹ are R 910-11"), a compound wherein ring C is a 5- or 6-membered heterocycle containing at least one atom nitrogen (hereinafter referred to as "ring C is C-1"), a compound wherein ring C is a six-membered heterocycle containing at least one nitrogen atom (hereinafter referred to as "ring C is C-2"), a compound wherein ring C is optionally substituted pyridine, optionally substituted pyrimidine, optionally substituted pyridazine, or optionally substituted pyrazine (hereinafter referred to as " uh C is C-3 "), a compound wherein ring C is optionally substituted pyridine or optionally substituted pyrimidine (hereinafter referred to as" ring C is C-4 "), a compound wherein ring C is

wherein CR 6 or N is CR 6 or Na 13, r 14 _and r 15 _are independently hydrogen, halogen, hydroxyl, optionally substituted lower alkyl, optionally substituted lower alkoxy, optionally substituted lower alkenyl, optionally substituted lower alkenyloxy, optionally substituted acyloxy, carboxyl, optionally substituted lower alkoxycarbonyl, optionally substituted lower alkenyloxycarbonyl, optionally substituted lower alkylthionyl, optionally substituted lower alkenylthionyl, optionally substituted amino, guanidine, nitro, optionally substituted lower alkylsulfonyl, optionally substituted lower alkylsulfonyloxy or optionally substituted lower alkylsulfonyloxy lower arylsulfonyloxy (hereinafter referred to as "ring C is C-5"), a compound wherein ring C is

or wherein wherein G ^ is CR ^ or N, G ^ is CR ^ or N, and R, R13 _J R14 _and R15 j _are independently of one another hydrogen, halogen, hydroxy, optionally substituted lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkoxy, optionally substituted amino or nitro (hereinafter referred to as "ring C is C-6"), a compound wherein ring C is C-5 and G 1 and G 2 are independently CH or N (hereinafter referred to as "ring" C is C-7 '), a compound wherein ring C is C-6 and G 1 and G 2 are independently CH or N (hereinafter referred to as "ring C is C-8"), a compound wherein ring C is

(hereinafter referred to as "Ring C is C-9")

AND

the compound, Me X and X 'are -O-, -CH 2 *, -NR (wherein R ¹ is hydrogen, optionally substituted lower alkoxy, lower alkenyl, lower alkylcarbonyl or optionally substituted lower alkoxycarbonyl) or -S (O) p -, where p is an integer between 0 and 2,

Y and Y 'are independently optionally substituted lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted amino, optionally substituted suamoyl, optionally substituted lower aryl or optionally substituted 5 or 6 membered heterocycle ,

Y is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl, or optionally substituted arylsulfonyl when X is -O- or -NR ¹ -,

Y 'is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl, or optionally substituted arylsulfonyl when X' is -O- or -NR ¹ -,

Y is hydrogen or halogen when X is -Cffy- or -NR ¹ - and Y 'is hydrogen or halogen when

X 'is -CH 2 - or -NR ¹ provided that Y and Y' are not simultaneously hydrogen (hereinafter referred to as Χ, X ', Y and Y' are XY-1), a compound wherein X and X 'are independently -O-, -CH ² -, -NR ¹ -, wherein R ¹ is hydrogen, optionally substituted lower alkyl, lower alkenyl, lower alkylcarbonyl, or optionally substituted lower alkoxycarbonyl or -S (O) p-, wherein p is an integer between 0 and 2,

Y and Y 'are independently optionally substituted lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkynyl, optionally substituted cycloalkyl, optionally substituted suamoyl, optionally substituted lower aryl or optionally substituted 5 or 6 membered heterocycle (denoted as "X, X") ', Y and Y' are XY-2 "), a compound wherein one of X and X 'is -O- and the other is -NR ¹ -, wherein R ¹ is hydrogen, optionally substituted lower alkyl, lower alkenyl, lower alkylcarbonyl or optionally substituted lower alkoxycarbonyl (hereinafter referred to as X, X ', Y and Y' are XY-3 '), a compound wherein one of X and X is -O- and the other is -NH- (you will be referred to as JC, X' , Y and Y 'are XY-4 "), a compound wherein at least one of Y and Y' is a prenyte (hereinafter referred to as" X, X ', Y and Y' are XY-5 "),

A compound wherein X and X 'are independently -O- or -NR ¹ -, wherein R ¹ is hydrogen, lower alkyl, lower alkenyl or optionally substituted lower alkoxycarbonyl,

Y and Y 'are independently optionally substituted lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkynyl, optionally substituted cycloalkyl, optionally substituted sulfamoyl, optionally substituted aryl or optionally substituted 5 or 6 membered heterocycle (hereinafter referred to as "X, X' , Y and Y 'are XY-6 "), a compound wherein one of X and X' is -O- and the other is -NR ¹ -, wherein R ¹ is hydrogen, lower alkyl, lower alkenyl or optionally substituted lower alkoxycarbonyl,

Y and Y 'are independently optionally substituted lower alkyl, optionally substituted lower alkenyl or optionally substituted lower alkynyl (hereinafter referred to as "X, X', Y and Y 'are XY-7"), a compound wherein one of X and X 'is -O- and the other is -NH, Y and Y' are independently optionally substituted lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkynyl, optionally substituted cycloalkyl, optionally substituted sulfamoyl, optionally substituted aryl or optionally substituted 5-membered or a six-membered heterocycle (hereinafter referred to as "X, X ', Ya Y' are XY-8"), a compound wherein one of X and X 'is -O- and the other is -NR ¹ -, wherein R ¹ is hydrogen, lower alkyl or lower alkenyl, Y and Y 'are independently optionally substituted lower alkyl or optionally substituted lower alkenyl (hereinafter referred to as "X, X', Y and Y 'are XY-9"), a compound wherein one of X and X 'is -O- and the other is -NH-, Y and Y 'are independently optionally substituted lower alkyl or optionally substituted lower alkenyl (hereinafter referred to as "X, X', Ya Y 'are XY-10"), a compound wherein one of X and X 'is -O- and the other is -NR ¹ -, wherein R ¹ is hydrogen, lower alkyl, lower alkenyl or optionally substituted lower alkoxycarbonyl, one of Y and Y' is lower alkyl or lower alkenyl and the other is optionally substituted lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkynyl, optionally substituted cycloalkyl, optionally substituted sulfamoyl, optionally substituted aryl or optionally substituted 5 or 6 membered heterocycle (hereinafter referred to as "X, X ', Y and Y' are XY- 11 '), a compound wherein one of X and X' is -O- and the other is -NH-, one of Y and Y 'is lower alkyl or lower alkenyl and the other is optionally substituted lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkynyl, optionally substituted cycloalkyl, optionally substituted sulfamoyph, optionally substituted aryl or optionally substituted 5 or 6 membered heterocycle (hereinafter referred to as "X, X ', Y and Y' are XY-12") ), a compound wherein one of X and X 'is -O- and the other is -NR 6 - where hydrogen, lower alkyl, lower alkenyl or optionally substituted lower alkoxycarbonyl, one of Y and Y' is lower alkyl or lower alkenyl and the other is hydrogen or optionally substituted lower alkyl, optionally substituted lower alkenyl, or optionally substituted lower alkynyl (hereinafter referred to as "X, X ', Ya Y' are XY-13"), a compound wherein one of X and X 'is - O- and the other is -NH-, one of Y and Y 'is lower alkyl or lower alkenyl and the other is hydrogen, optionally substituted lower alkyl, optionally substituted lower alkenyl or optionally substituted lower al kinyl (hereinafter referred to as "X, X ', Y and Y' are XY-14"), a compound wherein one of X and X 'is -O- and the other is -NR' * -, wherein R 6 is hydrogen, lower alkyl, lower alkenyl or optionally substituted lower alkoxycarbonyl, one of Y and Y 'is prenyl and the other is optionally substituted lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkynyl, optionally substituted cycloalkyl, optionally substituted sulfamoyl, optionally substituted aryl or optionally a substituted five or six membered heterocycle (hereinafter referred to as "X, X ', Y and Y' are XY 15"), a compound wherein one of X and X 'is -O- and the other is -NH-, one of Y and Y' is prenyl and the other is optionally substituted lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkynyl, optionally substituted cycloalkyl, optionally substituted sulfamoyl, optionally substituted aryl or optionally substituted five a linear or six-membered heterocycle (hereinafter referred to as "X, X ', Ya Y' are XY-16"), a compound wherein one of X and X 'is -O- and the other is -NR 6 -, wherein R ¹ is hydrogen , lower alkyl, lower alkenyl or optionally substituted lower alkoxycarbonyl, one of Y and Y 'is prenyl and the other is hydrogen, optionally substituted lower alkyl, optionally substituted lower alkenyl or optionally substituted lower alkynyl (hereinafter referred to as "X, X', Y") and Y 'are XY-17 "), a compound wherein one of X and X' is -O- and the other is -NH-, one of Y and Y 'is prenyl and the other is hydrogen, optionally substituted lower alkyl, optionally substituted lower alkenyl or optionally substituted lower alkynyl (hereinafter referred to as "X, X ', Y and Y'is XY-18"); A compound wherein one of -XY and -X'-Y 'is optionally substituted a lower alkyl alkylamine or an optionally substituted lower alkenylamine and the other is an optionally substituted lower alkoxy or an optionally substituted lower alkenyloxy group (hereinafter referred to as "X, X ', Y and Y'is XY-19"), a compound wherein one of -XY and - X'-Y 'is an optionally substituted lower alkylamine or an optionally substituted lower alkenylamine and the other is an optionally substituted lower prenyloxy group (hereinafter referred to as "X, X', Y and Y 'are XY-20"), a compound wherein R ⁴ and R ® are R45-1 and R® and ^R7 are R67-1, a compound wherein R ⁴ and R® are R45-1 and R® and ^R7 are R67-2, a compound wherein ^R4 and R45- are R® 2 and R ® and R ⁷ are R67-1, a compound wherein R ⁴ and R ® are R45-2 and R ® and R ⁷ are R67-2, a compound wherein R ⁴ and R ® are R45-3 and R ® and ^R7 are R67-1, a compound wherein R ⁴ and R® are R45-3 and R® and ^R7 are R67-2, a compound wherein R ⁴ and R® are R45-4 and R® and ^R7 are R67-1, a compound wherein R ⁴ and R ® are R 45-4 and R ® and R ⁷ are R67-2, a compound wherein R ⁴ and R ® are R 45-5 and R ® and R ⁷ are R67-1, a compound wherein R ⁴ and R ® are R45-5 and R ® and R ⁷ are R67-2, a compound wherein R ⁴ and R ® are R45-6 and R® and ^R7 are R67-1, a compound wherein R ⁴ and R® are R45-6 and R® and ^R7 are R67-2, a compound wherein ^R4 and R45- are R® 7 R® and ^R7 are R67-1, a compound wherein R ⁴ and R® are R45-7 and R® and ^R7 are R67-2, a compound wherein R R® and are R811-2 and ^R9 and R ^ ® are R910-3, a compound wherein R ® and R ¹¹ are R811-2 and R ⁹ and R ¹ ® are R910-4, a compound wherein R ® and R ¹¹ are R811-2 and R ⁹ and R ^{9 1} ® are R910-5, a compound wherein R ® and R ¹¹ are R811-2 and R ⁹ and R ¹ ® are R910-6, a compound wherein R ® and R ¹¹ are R811-2 and R ⁹ and R ⁹ ® are R910-7, a compound wherein R ® and R ¹¹ are R811-2 and R ⁹ and R 8 ® are R910-8, a compound wherein R ® and R ⁸ are R811-2 and R ⁹ and R 8 ® are R910 -9, a compound wherein R 8 and R ¹¹ are R 811-2 and R ⁹ and R ^{9 are} R 910-10; .. .. · · · · · .. .. ·· compound wherein ^R and R ¹¹ are R811-2 and ^R9 and ^R10 are R910-11, a compound wherein ^R8 and ^R11 are R811-3 and R ⁹ and R ¹⁰ are R 910-3, a compound wherein R ⁸ and R ¹¹ are R 811-3 and R ⁹ and R ¹⁹ are R 910-4, a compound wherein R ⁸ and R ¹¹ are R 811-3 and R ⁹ and ^R10 are R910-5, a compound wherein ^R8 and ^R11 are R811-3 and ^R9 and ^R10 are R910-6, a compound wherein ^R8 and ^R11 are R811-3 and ^R9 and ^R10 are R910 -7 compound wherein ^R8 and ^R11 are R811-3 and ^R9 and ^R10 are R910-8, a compound wherein ^R8 and ^R11 are R811-3 and ^R9 and ^R10 are R910-9, a compound wherein ^R8 and ^R11 are R811-3 and ^R9 and ^R10 are R910-10, a compound wherein ^R8 and ^R11 are R811-3 and ^R9 and ^R10 are R910-11, a compound wherein R ⁸ and R ¹¹ are R 811-4 and R ⁹ and R ¹⁰ are R 910-3, a compound wherein R ⁸ and R ¹¹ are R 811-4 and R ⁹ and R ¹⁰ are R 910-4, a compound wherein R ⁸ and R ¹¹ are R811-4 and ^R9 and ^R10 are R910-5, a compound wherein ^R8 and ^R11 are R811-4 and ^R9 and ^R10 are R910-6, a compound wherein ^R8 and ^R11 are R811-4 and R ⁹ a ^R10 are R910-7, a compound wherein ^R8 and ^R11 are R811-4 and ^R9 and ^R10 are R910-8, a compound wherein ^R8 and ^R11 are R811-4 and ^R9 and ^R10 are R910 -9 compound wherein ^R8 and ^R11 are R811-4 and ^R9 and ^R10 are R910-10, a compound wherein R ⁸ and R ¹¹ are R811-4 and ^R9 and ^R10 are R910-11, a compound wherein R ⁸ and R ¹¹ are R 811-5 and R ⁹ and R ¹⁰ are R 910-1, a compound wherein R ⁸ and R ¹¹ are R 811-5 and R ⁹ and R ¹⁰ are R 910-2, a compound wherein R ⁸ and R ¹¹ are R 811-5 and R ⁹ and R ¹⁰ are R 910-3, a compound wherein R ⁸ and R ¹¹ are R 811-5, and R ⁹ and R ¹⁰ are R 910-4, a compound wherein R ⁸ and R ¹¹ are R 811- 5 and R ⁹ and R ¹⁰ are R 910-5, a compound wherein R ⁸ and R ¹¹ are R 811-5 and R ⁹ and R ¹⁰ are R 910-6, a compound wherein R ⁸ and R ¹¹ are R 811-5 and R ⁹ and ^R10 are R910-7, a compound wherein ^R8 and ^R11 are R811-5 and ^R9 and ^R10 are R910-8, a compound wherein ^R8 and ^R11 are R811-5 and ^R9 and ^R10 are R910-9, • fc fcfc fcfcfcfc ·· fc fcfc • • · · fcfcfc compound wherein ^R8 and R811 are ¹ compound wherein R R® and R81 are 1 compound wherein R ⁸ and R ^ are R811 compound wherein ^R8 and ^R11 are R811 compounds wherein R ⁸ and R ¹¹ are R811 compound wherein ^R8 and ^R11 are R811 compound wherein ^R8 and R ^ are R811 a compound wherein ^R8 and ^R11 are R811 compound wherein ^R8 and ^R11 are R811 compound wherein R ⁸ and R @ ¹ are the R811 compounds wherein R ⁸ and R ^ are R811 compound wherein ^R8 and R ^ are R811 a compound wherein ^R8 and R ^ are R811 compound wherein ^R8 and ^R11 are R811 compound wherein ^R8 and ^R11 are R811 compound wherein ^R8 and ^R11 are R811 compound wherein ^R8 and ^R1 ^ are R811 is a compound wherein R ⁸ and R ¹¹ are R811 compound wherein ^R8 and ^R11 are R811 is a compound wherein R ⁸ and R ^ are R811 compound wherein ^R8 and R ^ are R811 compound wherein ^R8 and R ^ are R811 a compound wherein R ⁸ and R ¹ ** are R811 compound wherein R ⁸ and R @ R811 are compounds wherein R ⁸ and R ¹¹ are R811 compound wherein R ⁸ and R ** are R811 ¹ compound wherein R ⁸ and R ⁸ are R 811 compound wherein R ⁸ and R ¹¹ are R 811 and R ⁹ and R ¹⁹ are R 910-10,5 and R ⁹ and R ¹⁹ are R 910-11, 6 and R ⁹ and R ¹⁹ are R 910-1, 6 and R ⁹ and R ¹⁹ are R 910-2, and R ⁹ and R ¹⁹ are R 910-3, 6 and R 9 ⁹ and R ¹⁹ are R910-4, 6 and R ⁹ and R ⁹ are R910-5, 6 and R ⁹ and R ¹⁹ are R910-6, 6 and R ⁹ and R ¹⁹ are R910-7, and R ⁹ and R ¹⁹ are R910-8, and R ⁹ and R ¹⁹ are R910-9, 6 and R ⁹ and R ¹⁹ are R910-10, and R ⁹ and R ¹⁹ are R910-11, and R ⁹ and R ¹⁹ are R910 -1, and R ⁹ and R ¹⁹ are R 910-2, and R ⁹ and R ¹⁹ are R 910-3, and R ⁹ and R ¹⁹ are R 910-4, and R ⁹ and R ¹⁹ are R 910-5, and R ⁹ and R ¹⁹ are R 910-6, and R ⁹ and R ¹⁹ are R 910-7, and R ⁹ and R ¹⁹ are R 910-8, and R ⁹ and R ⁹ are R 910-9, and R ⁹ and R ¹⁹ are R 910 -10, 7 and R ⁹ and R ¹⁹ are R910-11, and R ⁹ and R ¹⁹ are R910-1, and R ⁹ and R ¹⁹ are R910-2, and R ⁹ and R ¹⁹ are R910-3, and R ⁹ and R ^ ⁹ are R910-4, ftft ftft, ftft ftft, ftft ftft, ftft ftft, ftft ftft • · · ··· ·· ftft ♦ ftft ftft ftft ft ·· ·· compound wherein R® and R ¹¹ are R811-8 and R ¹ and R® ® are R910-5, a compound wherein R and R® ¹¹ are R811-8 and R ® and R ¹ ® are R910-6, a compound wherein R ® and R ¹¹ are R811-8 and R ® and R ¹ ® are R910-7, a compound wherein R ® and R ¹¹ are R811-8 and R ¹ and R® ® are R910-8, a compound wherein R® and R ¹¹ are R811-8 and R ¹ and R® ® are R910-9, a compound wherein R® and ^R11 are R811- 8 and R ® and R ¹ ® are R910-10, a compound wherein R ® and R ¹¹ are R811-8 and R ® and R ¹ ® are R910-11, a compound wherein R ® and R ¹¹ are R811-9 and R ® and R ¹ ®jsou R910-1, a compound wherein R® and R ¹¹ are R811-9 and R ¹ and R® ® are R910-2, a compound wherein R® and ^R11 are R811-9 and R® and R ¹ ® is R910-3, a compound wherein R ® and R ¹¹ are R811-9 and R ® and R ¹ ® are R910-4, a compound wherein R ® and R ¹¹ are R811-9 and R ® and R ¹ ® are R910-5, a compound wherein R ® and R ¹¹ are R811-9 and R ® and R ¹ ® are R910-6, a compound wherein R ® and R ¹¹ are R811-9 and R ® and R ¹ ® are R910-7, a compound wherein R® and R ¹¹ are R811-9 and R ¹ and R® ® are R910-8, a compound wherein R® and ^R11 are R811-9 and R® and R ¹ are ® R910- 9, slou Enina wherein R® and R ¹¹ are R811-9 and R ¹ and R® ® are R910-10, a compound wherein R® and R ¹¹ are R811-9 and R ¹ and R® ® are R910-11, a compound wherein R® and ^R11 are R811-10 and R ¹ and R® ® are R910-1, a compound wherein R® and ^R11 are R811-10 and R ¹ and R® ® are R910-2, a compound wherein R ® and ^R11 are R811-10 and R ¹ and R® ® are R910-3, a compound wherein R® and ^R11 are R811-10 and R ¹ and R® ® are R910-4, a compound wherein R® and R ¹¹ are R811-10 and R ® and R ¹ ® are R910-5, a compound wherein R ® and R ¹¹ are R811-10 and R ® and R ¹ ® are R910-6, a compound wherein R ® and R ¹¹ are R811-10 and R ® and R ¹ ® are R910-7, a compound wherein R ® and R ¹¹ are R811-10 and R ® and R ¹ ® are R910-8, a compound wherein R ® and R ¹¹ are R811 -10 and R ® and R ¹ ® are R910-9, the compound wherein R ® and R ¹¹ are R811-10 and R ® and R ¹ ® are R910-10, ·· ·· ····· · · 0 0 4 9 4 8

444 00 94 9 · «φ ΐ • 0 0 0 000 0 · ·· ·· 00 00 compound wherein R® and ^R11 are R811-10 and ^R9 and ^R19 are R910-11, a compound wherein R® and R ¹¹ are R811-11 and R ⁹ and R ¹⁹ are R910-1, a compound wherein R ® and R ¹¹ are R811-11 and R ⁹ and R ¹⁹ are R910-2, a compound wherein R ® and R ¹¹ are R811 -11 and R ⁹ and R ¹⁹ are R 910-3, a compound wherein R ⁸ and R ¹¹ are R 811-11 and R ⁹ and R ¹⁹ are R 910-4, a compound wherein R ⁸ and R ¹¹ are R 811-11 and R 9 ⁹ and R ¹⁹ are R910-5, a compound wherein R ® and R ¹¹ are R811-11 and R ⁹ and R ¹⁹ are R910-6, a compound wherein R ® and R ¹¹ are R811-11 and R ⁹ and R ¹⁹ are R910-7, a compound wherein R ® and R ¹¹ are R811-11 and R ⁹ and R ¹⁹ are R910-8, a compound wherein R ® and R ¹¹ are R811-11 and R ⁹ and R ¹⁹ are R910-9 , a compound wherein R ® and R ¹¹ are R811-11 and R ⁹ and R ¹⁹ are R910-10, a compound wherein R ® and R ¹¹ are R811-11 and R ⁹ and R ¹⁹ are R910-11, a compound wherein R @ ⁸ and R @ ¹¹ are R811-12 and R @ ⁹ and R @ ¹⁹ are R910-1, a compound wherein R @ ⁸ and R @ ¹¹ are R @ 811-12 and R @ ⁹ and R @ ¹⁹ are R910-2; stamps, where R® and ^R11 are R811-12 and ^R9 and ^R19 are R910-3, a compound wherein R® and ^R11 are R811-12 and ^R9 and ^R19 are R910-4, a compound wherein R R ⁸ and R ¹¹ are R 811-12 and R ⁹ and R ¹⁹ are R 910-5, a compound wherein R ⁸ and R ¹¹ are R 811-12 and R ⁹ and R ¹⁹ are R 910-6, a compound wherein R ⁸ and R ¹¹ are R811-12 and R ⁹ and R ¹⁹ are R910-7, a compound wherein R ® and R ¹¹ are R811-12 and R ⁹ and R ¹⁹ are R910-8, a compound wherein R ® and R ¹¹ are R811-12 and R ⁹ and R ¹⁹ are R 910-9, a compound wherein R ⁸ and R ¹¹ are R 811-12 and R ⁹ and R ¹⁹ are R 910-10, a compound wherein R ⁸ and R ¹¹ are R 811-12 and R ⁹ and R ¹⁹ is R910-11, a compound wherein R ⁴ and R ® are R45-1 and R ® and R ¹¹ are R811-3, a compound wherein R ⁴ and R ® are R45-1 and R ® and R ¹¹ are R811 -4, a compound wherein R ⁴ and R ® are R45-1 and R ® and R ¹¹ are R 811-5, a compound wherein R ⁴ and R ® are R45-1 and R ® and R ¹¹ are R811-6, a compound where R ⁴ and R ® are R45-1 and R ® and R ¹¹ are R811-7;

4 • 4

444 · 4

4 · 4 compound wherein R ⁴ and R ⁸ are R 45-1 and R ® and R ¹¹ are R 811-8, a compound wherein R ⁴ and R ⁸ are R 45-1 and R ® and R ¹¹ are R811-9, the compound wherein R ⁴ and R ⁸ are R 45-1 and R ⁸ and R ¹¹ are R 811-10, a compound wherein R ⁴ and R ⁸ are R 45-1 and R ⁸ and R ¹¹ are R 811-11, a compound wherein R ⁴ and R ⁸ are R 45-1 and R ⁸ and R ¹¹ are R 811-12, a compound wherein R ⁴ and R ⁸ are R 45-2 and R ⁸ and R ¹¹ are R 811-3, a compound wherein R ⁴ and R ⁸ are R45-2 and R ® and R ¹¹ are R811-4, a compound wherein R ⁴ and R ⁸ are R45-2 and R ® and R ¹¹ are R811-5, a compound wherein R ⁴ and R ⁸ are R45-2 and R ⁸ and R ¹¹ are R 811-6, a compound wherein R ⁴ and R ⁸ are R 45-2 and R ⁸ and R ¹¹ are R 811-7, a compound wherein R ⁴ and R ⁸ are R 45-2 and R ⁸ and R ^{8 11} is R811-8, a compound wherein R ⁴ and R ⁸ are R 45-2 and R ® and R ¹¹ are R811-9, a compound wherein R ⁴ and R ⁸ are R45-2 and R ® and R ¹¹ are R811-9 10, a compound wherein R ⁴ and R ⁸ are R 45-2 and R ® and R ¹¹ are R 811-11, a compound wherein R ⁴ and R ⁸ are R 45-2 and R ® and R ¹¹ are R811-12, the compound, wherein R ⁴ and R ⁸ j R45-3 and R ® and R ¹¹ are R811-1, a compound wherein R ⁴ and R ⁸ are R45-3 and R ® and R ¹¹ are R811-2, a compound wherein R ⁴ and R ⁸ are R45-3 and R ® and R ¹¹ are R 811-3, a compound wherein R ⁴ and R ⁸ are R 45-3 and R ® and R ¹¹ are R 811-4, a compound wherein R ⁴ and R ⁸ are R 45-3 and R ⁸ and R ¹¹ is R 811-5, a compound wherein R ⁴ and R ⁸ are R 45-3 and R ⁸ and R ¹¹ are R 811-6, a compound wherein R ⁴ and R ⁸ are R 45-3 and R ¹¹ and R ¹¹ are R 811 -7, a compound wherein R ⁴ and R ⁸ are R 45-3 and R ® and R ¹¹ are R 811-8, a compound wherein R ⁴ and R ⁸ are R 45-3 and R ® and R ¹¹ are R811-9, the compound wherein R ⁴ and R ⁸ are R 45-3 and R ⁸ and R ¹¹ are R 811-10, a compound wherein R ⁴ and R ⁸ are R 45-3 and R ⁸ and R ¹¹ are R 811-11, a compound wherein R ⁴ and ^R8 are R45-3 and R® and ^R11 are R811-12, a compound wherein R ⁴ and R ⁸ are R45-4 and R® and ^R11 are R811-1, · * 99 ······ A compound wherein R ⁴ and R ⁸ are R 45-4 and R ⁸ and R ¹ are R 811-2, a compound wherein R ⁴ and R ⁸ are R 45-4 and R ^8, and R ¹ 1 are R811-3, a compound wherein R ⁴ and R ⁸ are R 45-4 and R ⁸ and R ¹ are R 811-4, a compound wherein R ⁴ and R ⁸ are R 45-4 and R ⁸ and R ¹¹ are R 811-5, a compound wherein R ⁴ and R ⁵ are R 45-4 and R ⁸ and R ¹¹ are R 811-6, a compound wherein R ⁴ and R ⁵ are R 45-4 and R ⁸ and R ¹¹ are R 811-7, a compound wherein R ⁴ and R ⁸ are R 45 -4, and ^R8 and ^R11 are R811-8, a compound wherein ^R4 and ^R5 are R45-4 and ^R8 and ^R11 are R811-9, a compound wherein R ⁴ and R ⁵ are R45-4 and R ⁸ and R ¹¹ are R 811-10, a compound wherein R ⁴ and R ⁵ are R 45-4 and R ⁸ and R ¹¹ are R 811-11, a compound wherein R ⁴ and R ⁸ are R 45-4 and R ⁸ and R ¹¹ are R811-12, a compound wherein R ⁴ and R ⁸ are R45-5 and ^R8 and ^R11 are R811-1, a compound wherein R ⁴ and R ⁸ are R45-5 and ^R8 and ^R11 are R811-2 , a compound wherein R ⁴ and R ⁵ are R 45-5 and R ⁸ and R ¹¹ are R 811-3, a compound wherein R ⁴ and R ⁸ are R 45-5 and R ⁸ and R ¹¹ are R 811-4, a compound wherein R ⁴ and R ⁸ are R 45-5 and R ⁸ and R ¹¹ are R 811-5, a compound wherein R ⁴ and R ⁸ are R 45-5 and R ⁸ and R ¹¹ are R 811-6, a compound wherein R ⁴ and R 8 ⁸ are R45-5 and ^R8 and ^R11 are R811-7, a compound wherein R ⁴ and R ⁸ are R45-5 and ^R8 and ^R11 are R811-8, a compound wherein R ⁴ and R ⁸ are R45-5 and ^R8 and ^R11 are R811-9 , a compound wherein R ⁴ and R ⁸ are R 45-5 and R ⁸ and R ⁸ are R 811-10, a compound wherein R ⁴ and R ⁸ are R 45-5 and R ⁸ and R ⁸ are R 811-11, a compound wherein R ⁴ and R ⁸ are R 45-5 and R ⁸ and R ¹¹ are R 811-12, a compound wherein R ⁴ and R ⁸ are R 45-6 and R ⁸ and R ¹¹ are R 811-1, a compound wherein R ⁴ and R 8 ⁸ are R45-6 and R ⁸ and R @ ¹ are R811-2, a compound wherein R ⁴ and R ⁸ are R45-6 and ^R8 and ^R11 are R811-3, a compound wherein R ⁴ and R ⁸ are R45 -6 and R ⁸ and R ^{8 are} R 811-4, a compound wherein R ⁴ and R ⁸ are R 45-6 and R ⁸ and R ¹¹ are R 811-5, ·· ··· · ····

A compound wherein R ⁴ and R ⁸ are R 45-6 and R ® and are R811-6, a compound wherein R ⁴ and R ⁸ are R 45-6 and R ® and are R811-7, a compound wherein R ⁴ and R ⁸ are R 45-6 and R ⁸ and R ¹¹ are R 811-8, a compound wherein R ⁴ and R ⁸ are R 45-6 and R ⁸ and R ¹¹ are R 811-9, a compound wherein R ⁴ and R ⁸ are R 45-6 and R ⁸ and R ¹¹ are R 811-10, a compound wherein R ⁴ and R ⁸ are R 45-6 and R ⁸ and are R 811-11, a compound wherein R ⁴ and R ⁸ are R 45 -6 and R ⁸ and R ¹¹ are R 811-12, a compound wherein R ⁴ and R ⁸ are R 45-7 and R ⁸ and are R 811-1, a compound wherein R ⁴ and R ⁸ are R 45-7 and R ⁸ and R ¹¹ is R 811-2, a compound wherein R ⁴ and R ⁸ are R 45-7 and R ⁸ and are R 811-3, a compound wherein R ⁴ and R ⁸ are R 45-7 and R ⁸ and are R 811-4, a compound wherein R ⁴ and R ⁸ are R 45-7 and R ⁸ and are R 811-5, a compound wherein R ⁴ and R ⁸ are R 45-7 and R ⁸ and R ¹¹ are R 811-6, a compound wherein R ⁴ and R 8 ⁸ are R45-7 and ^R8 and ^R11 are R811-7, a compound wherein R ⁴ and R ⁸ are R45-7 and ^R8 and ^R11 are R811-8, a compound wherein R ⁴ and R ⁸ are R45- 7 and R ⁸ and R ¹¹ js ou R811-9, a compound wherein R ⁴ and R ⁸ are R45-7 and R ⁸ and are R811-10, a compound wherein R ⁴ and R ⁸ are R45-7 and R ⁸ and R ¹¹ are R811-11, a compound wherein R ⁴ and R ⁸ are R45-7 and ^R8 and ^R11 are R811-12, a compound wherein R ⁴ and R ⁸ are R45-1, ^R8 and ^R7 are R67-1, ^R8 and R ^ are R811-4 and ^R9 and ^R10 are R910-3, a compound wherein R ⁴ and R ⁸ are R45-1, ^R8 and ^R7 are R67-1, R® and ^R11 are R811-4 and ^R9 and R ¹⁸ are R 910-4, the compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ⁶ are R 811-4 and R ⁹ and R ¹⁸ are R 910-5, the compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ⁶ are R 811-4 and R ⁹ and R ¹⁸ are R 910-8, a compound wherein R ⁴ and R ⁸ are and ^R10 are R910-3, a compound wherein R ⁴ and R ^5, and R ¹⁰ are R910-4, a compound wherein R ⁴ and R ^5, and R ¹⁰ are R910-5, a compound wherein R ⁴ and R® are and R ¹⁰ are R 910-8, a compound wherein R ⁴ and R ⁹ are and R ¹⁹ are R 910-3, a compound wherein R ⁴ and R ⁹ are and R ¹⁰ are R 910-4, a compound wherein R ⁴ and R 9 are ® are and R ¹⁰ are R910-5, comb antifungal compound, wherein R ⁴ and are R® and ^R10 are R910-8, a compound wherein R ⁴ and are R® and ^R10 are R910-3, a compound wherein R ⁴ and R ^5, and R ¹⁰ are R910-4 , a compound wherein R ⁴ and R ® are and R ¹⁰ are R910-5, a compound wherein R ⁴ and R ® are and R ¹⁰ are R910-8, a compound wherein R ⁴ and R ® are and R ¹⁰ are R910- 3, a compound wherein R ⁴ and R ® are and R ¹⁰ are R 910-4, 99 99

9 9 9 ·

9

998 9 9 99

9

99999 99 ·

R45-1, ^R6 and ^R7 are R67-1

R45-1, ^R6 and ^R7 are R67-1

R45-1, ^R6 and ^R7 are R67-1

R45-1, ^R6 and ^R7 are R67-1

R45-1, ^{R6 and R7} are R67-1,

R45-1, R® and ^R7 are R67-1,

R45-1, R® and ^R7 are R67-1,

R45-1, R® and ^R7 are R67-1,

R45-1, R67-1 are R®aR ^7,

R45-1, ^R6 and ^R7 are R67-1,

R45-1, R® and ^R7 are R67-1,

R45-1, R® and ^R7 are R67-1,

R 45-2, R ® and R ⁷ are R67-1

R 45-2, R ® and R ⁷ are R67-1

99 99

9 9 9 ·

9

9 9 9 ·

9 9 9

99 R® and ^R11 are R811-7a R ^9, R ⁸ and R ¹¹ are R811-7aR ^9, R ⁸ and R ¹¹ are R811-7aR ⁹ R® and R ¹¹ are R ⁹ R811-7a

R @ ¹¹ and R @ ¹¹ are R @ 811-10 and R @ ⁹

R @ ⁸ and R @ ¹¹ are R811 - 10a R @ ⁹

R @ ⁸ and R @ ¹¹ are R811 - 10a R @ ⁹

R @ ⁸ and R @ ¹¹ are R811 - 10a R @ ⁹

R @ ⁸ and R @ ¹¹ are R811-12 and R @ ⁹

R @ ⁸ and R @ ¹¹ are R811-12 and R @ ⁹

R @ ⁸ and R @ ¹¹ are R811-12 and R @ ⁹

R®aR ¹¹ are R811-12aR ⁹ R® and R ¹ 1 are R811-4 and ^R9 are R®aR ¹¹ R811-4aR ⁹

9 · · • 9 9999 • 9 • 9 9 9 • 9 9 9 • 9 • 9 9 9 9 9 9 ·· · • 9 9 9 9 9 9 9 • 9 • 9 9 9 9 • 9 999 99 9 · 9 ·· 99

a compound wherein R ⁴ and R ⁸ are R 45-2, R ® and R 6? are R67-1, R®aR ^ are R811-4 and ^R9 and ^R10 are R910-5, a compound wherein R ⁴ and R ⁸ are R45-2, R® and ^R7 are R67-1, R® and R ¹¹ are R 811-4 and R ⁹ and R ¹⁰ are R 910-8, a compound wherein R ⁴ and R ⁸ are R 45-2, R ⁸ and R ⁷ are R 67-1, R ^{8 and} R ¹¹ are R 811-7 and R 8 ⁹ and R ¹⁰ are R 910-3, a compound wherein R ⁴ and R ⁸ are R 45-2, R ⁶ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-7 and R ⁹ and R ¹⁰ are R 910- 4, a compound wherein R ⁴ and R ⁸ are R 45-2, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ⁶ are R 811-7 and R ⁹ and R ¹⁰ are R 910-5, a compound wherein R ⁴ and R ⁸ are R 45-2, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ⁸ are R 811-7 and R ⁹ and R ¹⁰ are R 910-8, the compound wherein R ⁴ and R ⁸ are R 45-2 , R® and ^R7 are R67-1, R® and ^R11 are R811-10 and ^R9 and ^R10 are R910-3, a compound wherein R ⁴ and R ⁸ are R45-2, R® and ^R7 are R67-1, ^R8 and ^R11 are R811-10 and ^R9 and ^R10 are R910-4, a compound wherein R ⁴ and R ⁸ are R45-2, R® and ^R7 are R67-1, ^R8 and R ¹¹ are R 811-10 and R ⁹ and R ¹⁰ are R 910-5 compound wherein R ⁴ and R ⁸ are R 45-2, R ⁷ and R ⁷ are R 67-1, R ⁸ and ^R11 are R811-10 and ^R9 and ^R10 are R910-8, a compound wherein R ⁴ and R ⁸ are R45-2, R® and ^R7 are R67-1, ^R8 and ^R11 are R811-12 and R ⁹ and R ¹⁰ are R 910-3, a compound wherein R ⁴ and R ⁸ are R 45-2, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-12 and R ⁹ and R ¹⁰ are R910 -4, a compound wherein R ⁴ and R ⁸ are R 45-2, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-12 and R ⁹ and R ¹⁰ are R910-5, a compound wherein R ⁴ and R ⁸ are R45-2, R® and ^R7 are R67-1, R® and R are R811-12 and ^R9 and ^R10 are R910-8,

444 4 4 ·· 4 · 4 4 4 • 444 4444

444 44 44 4 44 44 compound wherein R ⁴ and R ® are R45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-4 and R ⁹ and R ¹⁰ are R910-3, compound wherein R ⁴ and R ® are R45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-4 and R ⁹ and R ¹⁰ are R910-4, a compound wherein R ⁴ and R ® are R45-3, R® and ^R7 are R67-1, R® and ^R11 are R811-4 and ^R9 and ^R10 are R910-5, a compound wherein R ⁴ and R® are R45-3, R® and ^R7 are R67-1, R® and ^R11 are R811-4 and ^R9 and ^R10 are R910-8, a compound wherein R ⁴ and R® are R45-3, R® and ^R7 are R67-1 , R® and ^R11 are R811-7 and ^R9 and ^R10 are R910-3, a compound wherein R ⁴ and R® are R45-3, R® and ^R7 are R67-1, R® and R ¹¹ are R 811-7 and R ⁹ and R ¹⁰ are R 910-4, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-7 and R ⁹ and R ^{9 10} are R910-5, the compound wherein R ⁴ and R ® are R45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-7 and R ⁹ and R ¹⁰ are R910-8, the compound wherein R ⁴ and R ® are R45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R ¹⁰ are R9 10-3, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R ¹⁰ are R910-4, a compound wherein R ⁴ and R ® are R45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R ¹ ® are R910-5, a compound wherein R ⁴ and R ® are R45-3, R® and ^R7 are R67-1, R® and ^R11 are R811-10 and ^R9 and ^R10 are R910-8, a compound wherein R ⁴ and R® are R45-3, R® and ^R7 are R67-1, R® and ^R11 are R811-12 and ^R9 and ^R10 are R910-3, a compound wherein R ⁴ and R® are R45-3, R® and ^R7 are R67-1, R ® and R ¹¹ are R811-12 and R ⁹ and R ¹⁰ are R910-4, • 49 44 9994 99 94

4 4 4 4 4 9 4 4 5

9 4 4 4 4 4 4

443 4 9 4 9 4 4 4 9 9

9 4 9 9 4

494 99 44 4 94 44 compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R67-1, R ⁸ and R ¹¹ are R811-12 and R ⁹ and R ¹⁸ are R910-5, the compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-12 and R ⁹ and R ¹⁸ are R 910-8, a compound wherein R ⁴ and R ⁸ are R45-4, ^R8 and ^R7 are R67-1, ^R8 and ^R11 are R811-4 and ^R9 and ^R18 are R910-3, a compound wherein R ⁴ and R ⁸ are R45-4, ^R8 and ^R7 are R67-1, ^R8 and ^R11 are R811-4 and ^R9 and ^R18 are R910-4, a compound wherein R ⁴ and R ⁸ are R45-4, ^R8 and ^R7 are R67-1 , ^R8 and ^R11 are R811-4 and ^R9 and ^R18 are R910-5, a compound wherein R ⁴ and R ⁸ are R45-4, ^R8 and ^R7 are R67-1, ^R8 and ^R11 are R811-4 and ^R9 and ^R18 are R910-8, a compound wherein R ⁴ and R ⁸ are R45-4, ^R8 and ^R7 are R67-1, ^R8 and ^R11 are R811-7 and ^R9 and ^R18 are R910-3, a compound wherein R ⁴ and R ⁸ are R45-4, ^R8 and ^R7 are R67-1, ^R8 and ^R11 are R811-7 and ^R9 and ^R18 are R910-4, a compound wherein R ⁴ and R ⁸ are R 45-4, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-7 and R ⁹ and R ¹⁸ are u R910-5, a compound wherein R ⁴ and R ⁸ are R45-4, ^R8 and ^R7 are R67-1, ^R8 and ^R11 are R811-7 and ^R9 and ^R18 are R910-8, a compound wherein R ⁴ and R ⁸ are R 45-4, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-10 and R ⁹ and R ¹⁸ are R 910-3, a compound wherein R ⁴ and R ⁸ are R45-4, ^R8 and ^R7 are R67-1, ^R8 and ^R11 are R811-10 and ^R9 and ^R18 are R910-4, a compound wherein R ⁴ and R ⁸ are R45-4, ^R8 and ^R7 are R67-1, ^R8 and ^R11 are R811-10 and ^R9 and ^R18 are R910-5, a compound wherein R ⁴ and R ⁸ are R45-4, ^R8 and ^R7 are R67-1, R ⁸ and R ¹¹ are R811-10 and R ⁹ and R ¹⁸ are R910-8, • · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · Where R ⁴ and R jsou are R 45-4, R a and R ⁷ are R67-1, R a and R ¹¹ are R a φ sloučenina sloučenina sloučenina sloučenina sloučenina sloučenina sloučenina sloučenina sloučenina sloučenina R811-12 and R ⁹ and R ¹ ® are R910-3, a compound wherein R ⁴ and R® are R45-4, R® and ^R7 are R67-1, R® and ^R11 are R811-12 and ^R9 and R ^{10 is} R 910-4, a compound wherein R ⁴ and R ⁹ are R45-4, R® and ^R7 are R67-1, R® and R @ ¹ are R811-12 and ^R9 and ^R1 ® are R910-5, a compound wherein R ⁴ and R® are R45-4, R® and ^R7 are R67-1, R® and ^R11 are R811-12 and ^R9 and ^R1 ® are R910-8, a compound described in [1], wherein X 'is -0-, -NR 1 -S (O) p - and ring C is an optionally substituted five-membered heterocycle containing one or two heteroatoms, a compound wherein R ⁴ and R ® are R 45-4 and ring C is C-1, a compound wherein R ® and R ¹¹ are R811-9, R ⁹ and R ¹ ® are R910-7 and C ring is C-1, a compound wherein R ⁴ and R® are R45-4 and C ring is C-2, a compound wherein R® and R 6 are R 811-9, R ⁹ and R ^{8 are} R 910-7 and ring C is C-2, a compound wherein R ⁴ and R ® are R 45-4 and ring C is C-4, a compound wherein R ® and R @ ¹ are R811-9, ^R9 and R ^ ® are R910-7 and C ring is C-4, a compound wherein X, Y, X 'and Y' are XY-3 and C ring is C-2 , a compound wherein X, Y, X 'and Y' are XY-3 and ring C is C-3, a compound wherein X, Y, X 'and Y' are XY-3 and ring C is C-4, the compound wherein X, Y, X 'and Y' are XY-3 and ring C is C-6, a compound wherein X, Y, X 'and Y' are XY-3 and ring C is C-8, a compound wherein X, Y, X 'and Y' are XY-3 and ring C is C -9, a compound wherein X, Y, X 'and Y' are XY-4 and ring C is C-2, a compound wherein X, Y, X 'and Y' are XY-4 and ring C is C-3 , a compound wherein X, Y, X 'and Y' are XY-4 and ring C is C-4, a compound wherein X, Y, X 'and Y' are XY-4 and ring C is C-6, the compound wherein X, Y, X 'and Y' are XY-4 and ring C is C-8, a compound wherein X, Y, X 'and Y' are XY-4 and ring C is C-9, a compound wherein X, Y, X 'and Y' are XY-5 and ring C is C-2, a compound wherein X, Y, X 'and Y' are XY-5 and ring C is C-3, a compound wherein X, Y, X 'and Y' are XY-5, and ring C is C-4, 9 9 9 9, A 9 9, 9 9 9 9 9 99 99 · 9 9 9 9999

A compound wherein X, Y, X 'and Y' are XY-5 and ring C is C-6, a compound wherein X, Y, X 'and Y' are XY-5 and ring C is C-8, a compound wherein X, Y, X 'and Y' are XY-5 and ring C is C-9, a compound wherein X, Y, X 'and Y' are XY-6 and ring C is C-2, a compound wherein X, Y, X 'and Y' are XY-6 and ring C is C-3, a compound wherein X, Y, X 'and Y' are XY-6 and ring C is C -4, a compound wherein X, Y, X 'and Y' are XY-6 and ring C is C-6, a compound wherein X, Y, X 'and Y' are XY-6 and ring C is C-8 , a compound wherein X, Y, X 'and Y' are XY-6 and ring C is C-9, a compound wherein X, Y, X 'and Y' are XY-7 and ring C is C-2, the compound wherein X, Y, X 'and Y' are XY-7 and ring C is C-3, a compound wherein X, Y, X 'and Y' are XY-7 and ring C is C-4, a compound wherein X, Y, X 'and Y' are XY-7 and ring C is C-6, a compound wherein X, Y, X 'and Y' are XY-7 and ring C is C-8, a compound wherein X, Y, X 'and Y' are XY-7 and ring C is C-9, a compound wherein X, Y, X 'and Y' are XY-8 and ring C is C-2, a compound wherein X, Y, X 'and Y' are XY-8 and ring C j e C-3, a compound wherein X, Y, X 'and Y' are XY-8 and ring C is C-4, a compound wherein X, Y, X 'and Y' are XY-8 and ring C is C -6, a compound wherein X, Y, X 'and Y' are XY-8 and ring C is C-8, a compound wherein X, Y, X 'and Y' are XY-8 and ring C is C-9 , a compound wherein X, Y, X 'and Y' are XY-9 and ring C is C-2, a compound wherein X, Y, X 'and Y' are XY-9 and ring C is C-3, the compound wherein X, Y, X 'and Y' are XY-9 and ring C is C-4, a compound wherein X, Y, X 'and Y' are XY-9 and ring C is C-6, a compound wherein X, Y, X 'and Y' are XY-9 and ring C is C-8, a compound wherein X, Y, X 'and Y' are XY-9 and ring C is C-9, a compound wherein X, Y, X 'and Y' are XY-10 and ring C is C-2, a compound wherein X, Y, X 'and Y' are XY-10 and ring C is C-3, a compound wherein X, Y, X 'and Y' are XY-10 and ring C is C-4, a compound wherein X, Y, X 'and Y' are XY-10 and ring C is C-6, a compound wherein X, Y, X ' and Y 'are XY-10 and ring C is C-8, a compound wherein X, Y, X' and Y 'are XY-10 and ring C is C-9, * 0 0000 • 0

900 • 0 ·· · 0 t

0 0 0 ♦ 0 0 ·

0 «·· compound wherein X, Υ, X 'and Y' compound wherein X, Υ, X 'and Y' compound wherein X, Υ, X 'and Y' compound wherein X, Υ, X 'and Y 'compound wherein X, Υ, X' and Y 'compound wherein X, Υ, X' and Y 'compound wherein X, Υ, X' and Y 'compound wherein X, Υ, X' and Y ' a compound wherein X, Υ, X 'and Y' compound wherein X, Υ, X 'and Y' compound wherein X, Υ, X 'and Y' compound wherein X, Υ, X 'and Y' compound, wherein X, Υ, X 'and Y' compound wherein X, Υ, X 'and Y' compound wherein X, Υ, X 'and Y' compound wherein X, Υ, X 'and Y' compound wherein X , Υ, X 'and Y' compound wherein X, Υ, X 'and Y' compound wherein X, Υ, X 'and Y' compound wherein X, Υ, X 'and Y' compound wherein X, Υ , X 'and Y' compound wherein X, Υ, X 'and Y' compound wherein X, Υ, X 'and Y' compound wherein X, Υ, X 'and Y' compound wherein X, Υ, X 'and Y' compound wherein X, Υ, X 'and Y' compound wherein X, Υ, X 'and Y' compound wherein X, Υ, X 'and Y compound wherein X, Υ, X' and Y ' a compound wherein X, Υ, X 'and Y compound wherein X, Υ, X' and Y col a compound wherein X, Υ, X 'and Y compound wherein X, Υ, X' and Y are XY-11 and ring C is C-2 are XY-11 and ring C is C-3 are XY-11 and ring C is C-4, are XY-11 and ring C is C-6, are XY-11 and ring C is C-8, are XY-11 and ring C is C-9, are XY-12 and ring C is C-2, are XY-12 and ring C is C-3, are XY-12 and ring C is C-4, are XY-12 and ring C is C-6, are XY-12 and ring C is C-8, are XY-12 and ring C is C-9, are XY-13 and ring C is C-2, are XY-13 and ring C is C-3, are XY-13 and ring C is C- 4, are XY-13 and ring C is C-6, are XY-13 and ring C is C-8, are XY-13 and ring C is C-9, are XY-14 and ring C is C-2, are XY-14 and ring C is C-3, are XY-14 and ring C is C-4, are XY-14 and ring C is C-6, are XY-14 and ring C is C-8, are XY -14 and ring C is C-9, are XY-15 and ring C is C-2, are XY-15 and ring C is C-3, are XY-15 and ring C is C-4, are XY-15 and ring C is C-6, are XY-15 and ring C is C-8, are XY-15 and ring C is C-9, are XY-16 and ring C is C-2, are XY-16 and ring C is C-3, XY-16 and ring C is C-4, 4444

44

4 • 4 • 4 • 4 • 4 • 4 • 4 • 4

4 * 4

4 *

4 4

4 4

4 4 4

4 * 4 44 compound wherein X, Y, X 'and Y compound wherein X, Y, X' and Y 'compound wherein X, Y, X' and Y compound wherein X, Y, X 'and Y 'compound wherein X, Y, X' and Y 'compound wherein X, Y, X' and Y 'compound wherein X, Y, X' and Y 'compound wherein X, Y, X' and Y 'compound wherein X, Y, X 'and Y' compound wherein X, Y, X 'and Y' compound wherein X, Y, X 'and Y' compound wherein X, Y, X 'and Y compound wherein X , Y, X 'and Y' compound wherein X, Y, X 'and Y' compound wherein X, Y, X 'and Y compound wherein X, Y, X' and Y 'compound wherein X, Y, X 'and Y' compound wherein X, Y, X 'and Y' compound wherein X, Y, X 'and Y' compound wherein X, Y, X 'and Y compound wherein X, Y, X' and Y compound wherein X, Y, X 'and Y compound wherein X, Y, X' and Y compound wherein X, Y, X 'and Y compound wherein X, Y, X' and Y 'compound wherein X , Y, X 'and Y compound wherein X, Y, X' and Y are XY-16 and ring C is C-6, are XY-16 and ring C is C-8, are XY-16 and ring C is C-9, are XY-17 and ring C is C-2, are XY-17 and ring C is C-3, are XY-17 and ring C is C- 4, are XY-17 and ring C is C-6, are XY-17 and ring C is C-8, are XY-17 and ring C is C-9, are XY-18 and ring C is C-2, are XY-18 and ring C is C-3, are XY-18 and ring C is C-4, are XY-18 and ring C is C-6, are XY-18 and ring C is C-8, are XY -18 and ring C is C-9, are XY-19 and ring C is C-2, are XY-19 and ring C is C-3, are XY-19 and ring C is C-4, are XY-19 and ring C is C-6, are XY-19 and ring C is C-8, are XY-19 and ring C is C-9, are XY-20 and ring C is C-2, are XY-20 and ring C is C-3, are XY-20 and ring C is C-4, are XY-20 and ring C is C-6, are XY-20 and ring C is C-8, are XY-20 and ring C is C-9, a compound wherein R ⁴ and R 8 are R 45-1, R ⁸ and R 8; are R67-1, R® and ^R11 are R811-4 and ^R9 and ^R10 are R910-4, X, Y, X 'and Y' are XY-5 and C ring is C-3, a compound wherein R ⁴ and ^R5 are R45-1, ^R6 and ^R7 are R67-1, R® and ^R11 are R811-4 and ^R9 and ^R10 are R910-4, X, Y, X 'and Y' are XY -5 and ring C is C-4, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R67 -1, R ⁸ and R @ ¹ are R811-4 and ^R9 and ^R10 are R910-4, X, Y, X 'and Y' are XY-5 and C ring is C-6, a compound wherein R ⁴ and ^R8 are R45-1, ^R8 and ^R7 are R67-1, ^R8 and ^R11 are R811-4 and ^R9 and ^R18 are R910-4, X, Y, X 'and Y' are XY- 5 and ring C is C-9, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-4 and R ⁹ and R ¹⁹ are R 910- 4, X, Y, X 'and Y' are XY-6 and ring C is C-3, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R67-1, R ⁸ and R ¹¹ are R811-4 and ^R9 and ^R19 are R910-4, X, Y, X 'and Y' are XY-6 and C ring is C-4, a compound wherein R ⁴ and R ⁸ are R45-1, ^R6 and ^R7 are R67-1, ^R8 and ^R11 are R811-4 and ^R9 and R ¹⁹ are R 910-4, X, Y, X 'and Y' are XY-6 and ring C is C-6, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67- 1, R ⁸ and R ¹¹ are R 811-4 and R ⁹ and R ¹⁹ are R 910-4, X, Y, X 'and Y' are XY-6 and ring C is C-9, a compound wherein R ⁴ and R ⁸ are R45-1, ^R8 and ^R7 are R67-1, ^R8 and R ¹¹ are R811-4 and ^R9 and ^R19 are R910-4, X, Y, X 'and Y' are XY-9 and the ring C is C-3, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-4 and R ⁹ and R ¹⁹ are R 910-4, X , Y, X 'and Y' are XY-9 and ring C is C-4, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R67-1, R ⁸ and R ¹¹ are R811 -4 and R ⁹ and R ¹⁹ are R 910-4, X, Y, X 'and Y' are XY-9 and ring C is C-6, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-4 and R ⁹ and R ¹⁹ are R 910-4, X, Y, X 'and Y' are XY-9 and ring C is C-9, the compound, wherein R ⁴ and R ⁸ are R45-1, ^R8 and ^R7 are R67-1, ^R8 and R ^ are R811-4 and ^R9 and ^R19 are R910-4, X, Y, X 'and Y' are XY-17 and ring C is C-3, a compound wherein R ⁴ and R ⁸ are R 45-1 R ⁸ and R ⁷ are R67-1, ^R8 and ^R11 are R811-4 and ^R9 and ^R19 are R910-4, X, Y, X 'and Y' are XY-17 and C ring is C 4, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-4 and R ⁹ and R ¹⁹ are R 910-4, X, Y, X 'and Y' are XY-17 and ring C is C-6, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-4 and R 8 ⁹ and r 10 are R910-4, X, Y, X 'and Y' are XY-17 and ring C is C-9; a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R® and ^R11 are R811-4 and R® and ^R10 are R910-5, X, Y, X 'and Y' are XY-5 and C ring is C-3, a compound wherein R R® and ⁴ are R45-1, R® and ^R7 are R67-1, R® and ^R11 are R811-4 and R® and ^R10 are R910-5, X, Y, X 'and Y' are XY -5 and ring C is C-4, a compound wherein R ⁴ and R ® are R45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-4 and R ® and R ¹⁰ are R910 -5, X, Y, X 'and Y' are XY-5 and ring C is C-6, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ⁸ and R ¹¹ are R 811-4 and R ⁸ and R ¹⁰ are R 910-5, X, Y, X 'and Y 'are XY-5 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-4 and R ® and R ¹⁰ are R 910-5, X, Y, X 'and Y' are XY-6 and ring C is C-3, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1 , R® and ^R11 are R811-4 and R® and ^R10 are R910-5, X, Y, X 'and Y' are XY-6 and C ring is C-4, a compound wherein R ⁴ and R® are R45-1, R® and ^R7 are R67-1, R® and ^R11 are R811-4 and R® and ^R10 are R910-5, X, Y, X 'and Y' are XY-6 and the ring C is C-6, a compound wherein R ⁴ and R ® are R45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-4 and R ® and R ¹⁰ are R910-5, X , Y, X 'and Y' are XY-6 and ring C is C-9, a compound wherein R ⁴ and R ® are R45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811 -4 and R ® and R ¹⁰ are R 910-5, X, Y, X 'and Y' are XY-9 and ring C is C-3, the compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-4 and R ⁸ and R ¹⁰ are R 910-5, X, Y, X 'and Y' are XY-9 and ring C is C-4, the compound, wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R 67-1, R ® and ^R11 are R811-4 and R® and ^R10 are R910-5, X, Y, X 'and Y' are XY-9 and C ring is C-6, a compound wherein ^R4 and R45- are R® 1 R® and ^R7 are R67-1, R® and ^R11 are R811-4 and R® and ^R10 are R910-5, X, Y, X 'and Y' are XY-9 and C ring is C -9, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-4 and R ® and R ¹⁰ are R910-5, X, Y, X 'and Y' are XY-17 and ring C is C-3, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-4 and R® and ^R10 are R910-5, X, Y, X 'and Y' are XY-17 and C ring is C-4, • ·· · · · · · · · · * ♦ • · compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ⁸ are R 811-4 and R ⁹ and R ¹⁰ are R 910-5, X, Υ, X 'and Y' are XY -17 and ring C is C-6, the compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R67-1, R ® and R ¹¹ are R811-4 and R ⁹ and R ¹⁰ are R910 -5, X, Υ, X 'and Y' are XY-17 and ring C is C-9, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R67-1, R ® and ^R11 are R811-4 and ^R9 and ^R10 are R910- 7, X, Υ, X 'and Y' are XY-5 and ring C is C-3, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁷ and R ⁷ are R 67-1, R ^{8 and} R ¹¹ are R811-4 and ^R9 and ^R10 are R910-7, X, Υ, X 'and Y' are XY-5 and C ring is C-4, a compound wherein R ⁴ and R ⁸ are R45-1, R ⁸ and ^R7 are R67-1, ^R8 and ^R11 are R811-4 and ^R9 and ^R10 are R910-7, X, Υ, X 'and Y' are XY-5 and C ring is C-6, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ⁷ and R ⁶ are R 811-4 and R ⁹ and R ¹⁰ are R 910-7, X, Υ, X 'and Y are XY-5 and ring C is C-9, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-4 and R ⁹ and R 8 ¹⁰ are R910-7, X, Υ, X 'and Y' are XY-6 and ring C is C-3, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R67-1, R ⁸ and R ¹¹ are R 811-4 and R ⁹ and R ¹⁰ are R 910-7, X, Υ, X 'and Y' are XY-6 and ring C is C-4, the compound wherein R ⁴ and R ⁸ are R45-1, ^R8 and ^R7 are R67-1, ^R8 and ^R11 are R811-4 and ^R9 and ^R10 are R910-7, X, Υ, X 'and Y' are XY-6 and C ring is C-6, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R67-1, R®aR ¹¹ are R811-4 and ^R9 and ^R10 are R910-7, X, Υ, X 'and Y' are XY-6 and C ring is C-9, a compound wherein R ⁴ and ^R8 are R45-1, R® and ^R7 are R67-1, ^R8 and are R811-4 and ^R9 and ^R10 are R910-7, X, Υ, X 'and Y' are XY-9 and ring C is C-3, the compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ⁷ and R ¹¹ are R 811-4 and R ⁹ and R ¹⁰ are R 910-7, X , Υ, X 'and Y' are XY-9 and ring C is C-4, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ^{8 and} R ¹¹ are R 811- 4 and R ⁹ and R ¹⁰ are R 910-7, X, Υ, X 'and Y' are XY-9 and ring C is C-6, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R67-1, ^R8 and R ^ ¹ are R811-4 and ^R9 and ^R10 are R910-7, X, Υ, X 'and Y' are XY-9 and C ring is C-9,

a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-4 and R ⁹ and R ¹⁹ are R 910-7, X, Υ, X 'and Y 'are XY-17 and ring C is C-3, a compound wherein R ⁴ and R ⁸ are R 45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-4 and R ⁹ and R ¹⁹ are R 910-7, X, Υ, X 'and Y' are XY-17 and ring C is C-4, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁶ and R ⁷ are R67-1 , R ® and R ¹¹ are R 811-4 and R ⁹ and R ¹⁹ are R 910-7, X, Υ, X 'and Y' are XY-17 and ring C is C-6, a compound wherein R ⁴ and R ⁸ are R45-1, R® and ^R7 are R67-1, R® and ^R11 are R811-4 and ^R9 and ^R19 are R910-7, X, Υ, X 'and Y' are XY-17 and the ring C is C-9, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁶ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-8 and R ⁹ and R ¹⁹ are R 910-4, X , Υ, X 'and Y' are XY-5 and ring C is C-3, a compound wherein R ⁴ and R ⁸ are R 45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811 -8 and R ⁹ and R ¹⁹ are R 910-4, X, Υ, X 'and Y' are XY-5 and ring C is C-4, a compound wherein R ⁴ and R ⁸ are R 45-1, R ® and R ⁷ are R 67-1, R ⁷ and R ¹¹ are R 811-8 and R ⁹ and R ¹⁹ are R 910-4, X, Υ, X 'and Y' are XY-5 and ring C is C-6, a compound wherein R ⁴ and R ⁸ are R 45-1, R ® and R ⁷ are R67-1, R® and ^R11 are R811-8 and ^R9 and ^R19 are R910-4, X, Υ, X 'and Y' are XY-5 and C ring is C-9, a compound wherein R ⁴ and R ⁸ are R 45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-8 and R ⁹ and R ¹⁹ are R910-4, X, Υ, X 'and Y' are XY -6 and ring C is C-3, a compound wherein R ⁴ and R ⁸ are R 45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-8 and R ⁹ and R ¹⁹ are R910 -4, X, Υ, X 'and Y' are XY-6 and ring C is C-4, a compound wherein R ⁴ and R ⁸ are R 45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R 811-8 and R ⁹ and R ¹⁹ are R 910-4, X, Υ, X 'and Y' are XY-6 and ring C is C-6, the compound wherein R ⁴ and R ⁸ are R 45-1 , R® and ^R7 are R67-1, R® and ^R11 are R811-8 and ^R9 and ^R19 are R910-4, X, Υ, X 'and Y' are XY-6 and C ring is C 9, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-8 and R ⁹ and R ¹⁹ are R 910-4, X, Υ, X 'and Y' are XY-9 and ring C is C-4, a compound wherein R ⁴ and ^R8 are R45-1, R® and ^R7 are R67-1, R® and ^R11 are R811-8 and ^R9 and ^R19 are R910-4, X, Υ, X 'and Y' are XY- 9 and ring C is C-6, 44 • 4 · 9 4 4 9 9 4

444 4 9 4 4 4 4 44 9 • 4 4 4 9 4 9

A compound wherein R ⁴ and R ® are R45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-8 and R ⁹ and R ¹⁰ are R910-4, X, Y, X 'and Y' are XY-9 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ⁸ and R ¹¹ are R 811-8 and R ⁹ and R ¹⁰ are R 910-4, X, Y, X 'and Y' are XY-17 and ring C is C-4, a compound wherein R ⁴ and R ® are R 45-1, R ® and ^R7 are R67-1, R® and ^R11 are R811-8 and ^R9 and ^R10 are R910-4, X, Y, X 'and Y' are XY-17 and C ring is C-6, compound wherein R ⁴ and R ® are R45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-8 and R ⁹ and R ¹⁰ are R910-4, X, Y, X 'and Y are XY-17 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-8 and R ⁹ and R 7 ¹⁰ are R910-5, X, Y, X 'and Y' are XY-5 and ring C is C-4, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ⁸ and R ¹¹ are R 811-8 and R ⁹ and R ¹⁰ are R 910-5, X, Y, X 'and Y' are XY-5 and ring C is C-6, the compound wherein R ⁴ and R ⁸ are R45-1, R® and ^R7 are R67-1, ^R11 R® and j R 811-8 and R ⁹ and R ¹⁰ are R 910-5, X, Y, X 'and Y' are XY-5 and ring C is C-9, a compound wherein R ⁴ and R ® are R45-1, R R ⁷ and R ⁷ are R 67-1, R ⁷ and R ¹¹ are R 811-8 and R ⁹ and R ¹⁰ are R 910-5, X, Y, X 'and Y' are XY-6 and ring C is C-4, the compound wherein R ⁴ and R ® are R45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-8 and R ⁹ and R ¹⁰ are R910-5, X, Y, X 'and Y are XY-6 and ring C is C-6, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-8 and R ⁹ and R 7 ¹⁰ are R910-5, X, Y, X 'and Y' are XY-6 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ⁸ and R ¹¹ are R 811-8 and R ⁹ and R ¹⁰ are R 910-5, X, Y, X 'and Y' are XY-9 and ring C is C-4, the compound wherein R ⁴ and R ⁸ are R45-1, R® and ^R7 are R67-1, R® and ^R11 are R811-8 and ^R9 and ^R10 are R910-5, X, Y, X 'and Y' are XY-9 and C ring is C-6, a compound wherein R ⁴ and R ® are R45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-8 and R ⁹ and R ¹⁰ are R910-5, X, Y, X 'and Y' are XY-9, and ring C is C-9, a compound wherein R 1 R® and ⁴ are R45-1, R® and ^R7 are R67-1, R® and ^R11 are R811-8 and ^R9 and ^R10 are R910-5, X, Y, X 'and Y' are XY -17 and ring C is C-4,

* · «· 9 • 9994 ♦ · * 4 4 99 9 4 »·· · t * 4 4 « 4 * · • « 4 4 4 4 • 4 9 · 44 • »· 4 4

a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-8 and R ⁹ and R ¹⁰ are R 910-5, X, Y, X 'and Y 'are XY-17 and ring C is C-6, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-8 and R ⁹ and R ¹⁰ are R 910-5, X, Y, X 'and Y' are XY-17 and ring C is C-9, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R67-1 , R ⁸ and R ¹¹ are R 811-8 and R ⁹ and R ¹⁰ are R 910-7, X, Y, X 'and Y' are XY-5 and ring C is C-4, a compound wherein R ⁴ and R ⁸ are R45-1, ^R8 and ^R7 are R67-1, ^R8 and ^R11 are R811-8 and ^R9 and ^R10 are R910-7, X, Y, X 'and Y' are XY-5 and the ring C is C-6, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-8 and R ⁹ and R ¹⁰ are R 910-7, X , Y, X 'and Y' are XY-5 and ring C is C-9, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R67-1, R ⁸ and R ¹¹ are R811 -8 and R ⁹ and R ¹⁰ are R 910-7, X, Y, X 'and Y' are XY-5 and ring C is C-4, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-8 and R ⁹ a R ¹⁰ are R 910-7, X, Y, X 'and Y' are XY-5 and ring C is C-6, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R67-1 , R ⁸ and R ¹¹ are R 811-8 and R ⁹ and R ¹⁰ are R 910-7, X, Y, X 'and Y' are XY-5 and ring C is C-9, a compound wherein R ⁴ and R ⁸ are R45-1, ^R8 and ^R7 are R67-1, ^R8 and ^R11 are R811-8 and ^R9 and ^R10 are R910-7, X, Y, X 'and Y' are XY-6 and the ring C is C-4, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-8 and R ⁹ and R ¹⁰ are R 910-7, X , Y, X 'and Y' are XY-6 and ring C is C-6, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R67-1, R ⁸ and R ¹¹ are R811 -8 and R ⁹ and R ¹⁰ are R 910-7, X, Y, X 'and Y' are XY-6 and ring C is C-9, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-8 and R ⁹ and R ¹⁰ are R 910-7, X, Y, X 'and Y' are XY-9 and ring C is C-4, the compound, wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-8 and R ⁹ and R ¹⁰ are R 910-7, X, Y, X 'and Y' are XY-9 and ring C is C-6, a compound wherein R ⁴ and R ⁸ are R 45-1 R ⁸ and R ⁷ are R67-1, ^R8 and ^R11 are R811-8 and ^R9 and ^R10 are R910-7, X, Y, X 'and Y' are XY-9 and C ring is C 9,

a compound wherein R ⁴ and R ® are R 45-1, R ⁶ and R ⁷ are R 67-1, R ® and R ¹¹ are R 811-8 and R ⁹ and R ¹⁹ are R 910-7, X, Y, X 'and Y 'are XY-17 and ring C is C-4, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-8 and R ⁹ and R ¹⁹ are R 910-7, X, Y, X 'and Y' are XY-17 and ring C is C-6, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1 , R ® and R ¹¹ are R 811-8 and R ⁹ and R ¹⁹ are R 910-7, X, Y, X 'and Y' are XY-17 and ring C is C-9, a compound wherein R ⁴ and R ⁸ are R45-1, R® and ^R7 are R67-1, R® and ^R11 are R811-10 and ^R9 and ^R19 are R910-4, X, Y, X 'and Y' are XY-5 and the ring C is C-4, a compound wherein R ⁴ and R ® are R45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R ¹⁹ are R910-4, X , Y, X 'and Y' are XY-5 and ring C is C-6, a compound wherein R ⁴ and R ® are R45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811 -10 and R ⁹ and R ¹⁹ are R 910-4, X, Y, X 'and Y' are XY-5 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-1, R ® and ^R7 are R67-1, R® and ^R11 are R811-10 and R ⁹ and R ¹⁰ are R910-4, X, Y, X 'and Y' are XY-6 and C ring is C-4, a compound wherein R ⁴ and R® are R45-1, R® and ^R7 is R67 -1 R® and ^R11 are R811-10 and ^R9 and ^R10 are R910-4, X, Y, X 'and Y' are XY-6 and C ring is C-6, a compound wherein R ⁴ and R® are R45-1, R® and ^R7 are R67-1, R® and ^R11 are R811-10 and ^R9 and ^R19 are R910-4, X, Y, X 'and Y' are XY-6 and ring C is C-9, a compound wherein R ⁴ and R ® are R45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-1.0 and R ⁹ and R ¹⁹ are R910-4 , X, Y, X 'and Y' are XY-9 and ring C is C-4, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and ^R9 and ^R19 are R910-4, X, Y, X 'and Y' are XY-9 and C ring is C-6, a compound wherein R ⁴ and R® are R45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R ¹⁹ are R910-4, X, Y, X 'and Y' are XY-9 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R ¹⁹ are R910-4, X, Y, X 'and Y 'are XY-17 and ring C is C-4, a compound wherein R ⁴ a R® are R45-1, R® and ^R7 are R67-1, R® and ^R11 are R811-10 and ^R9 and ^R19 are R910-4, X, Y, X 'and Y' are XY-17 and ring C is C-6, 0 · 0 · 0 · 0 · 0 · 0 · 0 · 0 · 0 · 0 · 0 · 0 · 0 · 0 · 0 · 0 · 0 · 0 · 0 · 0 · 0 · 0 · 0 Compound where R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R ¹⁰ are R910-4, X, Y, X 'and Y' are XY-17 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ® and ^R11 are R811-10 and ^R9 and ^R10 are R910-5, X, Y, X 'and Y' are XY-5 and C ring is C-4, a compound wherein ^R4 and R45- are R® 1 R® and ^R7 are R67-1, R® and ^R11 are R811-10 and ^R9 and ^R10 are R910-5, X, Y, X 'and Y' are XY-5 and C ring is C -6, a compound wherein R ⁴ and R ® are R45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R ¹⁰ are R910-5, X, Y, X 'and Y' are XY-5 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R ¹⁰ are R 910-5, X, Y , X 'and Y' are XY-6 and ring C is C-4, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R ¹⁰ are R 910-5, X, Y, X 'and Y' are XY-6 and ring C is C-6, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R® and ^R11 are R811-10 and ^R9 and ^R10 are R910-5, X, Y, X 'and Y' are XY-6 and C ring is C-9, a compound wherein R R® and ⁴ are R45-1, R® and ^R7 are R67-1, R® and ^R11 are R811-10 and ^R9 and ^R10 are R910-5, X, Y, X 'and Y' are XY -9 and ring C is C-4, the compound wherein R ⁴ and R ® are R45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R ¹⁰ are R910 -5, X, Y, X 'and Y' are XY-9 and ring C is C-6, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R 811-10 and R ⁹ and R ¹⁰ are R 910-5, X, Y, X 'and Y' are XY-9 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-1 , R® and ^R7 are R67-1, R® and ^R11 are R811-10 and ^R9 and ^R10 are R910-5, X, Y, X 'and Y' are XY-17 and C ring is C 4, a compound wherein R ⁴ and R® are R45-1, R®, and R ⁷ j sou R67-1, R® and ^R11 are R811-10 and ^R9 and ^R10 are R910-5, X, Y, X 'and Y' are XY-17 and C ring is C-6, a compound wherein R R® and ⁴ are R45-1, R® and ^R7 are R67-1, R® and ^R11 are R811-10 and ^R9 and ^R10 are R910-5, X, Y, X 'and Y' are XY -17 and ring C is C-9, a compound wherein R ⁴ and R ® are R45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R ¹⁰ are R910 -7, X, Y, X 'and Y' are XY-5 and ring C is C-4, · ···· · · · · · · · · · · · · · · · · A compound wherein R ⁴ and R ® are R45-1, R ® and R ⁷ are R67-1, R ® and R ⁶ are R811-10 and R ⁹ and R ¹⁰ are R910-7, X, Y, X 'and Y' are XY-5 and ring C is C-6, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R 811-10 and R ⁹ and R ¹⁰ are R 910-7, X, Y, X 'and Y' are XY-5 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45- 1 R® and ^R7 are R67-1, R® and ^R11 are R811-10 and ^R9 and ^R10 are R910-7, X, Y, X 'and Y' are XY-6 and C ring is C -4, a compound wherein R ⁴ and R ® j sou R45-1, R® and ^R7 are R67-1, ^R8 and ^R11 are R811-10 and ^R9 and ^R19 are R910-7, X, Y, X 'and Y' are XY-6 and the ring C is C-6, a compound wherein R ⁴ and R ® are R45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R ¹⁰ are R910-7, X , Y, X 'and Y' are XY-6 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ® and R ⁶ are R811 -10 and R ⁹ and R ¹⁰ are R 910-7, X, Y, X 'and Y' are XY-9 and ring C is C-4, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R 811-10 and R ⁹ and R ¹⁰ are R 910-7, X, Y, X 'and Y' are XY-9 and ring C is C-6, the compound, wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ⁸ are R 811-10 and R ⁹ and R ¹⁰ are R 910-7, X, Y, X 'and Y' are XY-9 and ring C is C-9, a compound wherein R ⁴ and R ® are R45-1, R ® and R ⁷ are R67-1, R ^{8 and} R ¹¹ are R811-10 and R ⁹ and R ¹⁰ are R910 -7, X, Y, X 'and Y' are XY-17 and ring C is C-4, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R 811-10 and R ⁹ and R ¹⁰ are R 910-7, X, Y, X 'and Y 'are XY-17 and ring C is C-6, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ® and R ⁶ are R 811-10 and R ⁹ and R ¹⁰ are R 910-7, X, Y, X 'and Y' are XY-17 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1 , ^R8 and ^R11 are R811-4 and ^R9 and ^R10 are R910-4, X, Y, X 'and Y' are XY-5 and C ring is C-4, a compound wherein R ⁴ and R® are R45-3, R® and ^R7 are R67-1, R® and ^R11 are R811-4 and ^R9 and ^R10 are R910-4, X, Y, X 'and Y' are XY-5 and the ring C is C-6, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-4 and R ⁹ and R ¹⁰ are R910-4, X , Y, X 'and Y' are XY-5 and ring C is C-9,

a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ⁶ are R 811-4 and R ⁹ and R ¹⁰ are R 910-4, X, Y, X 'and Y are XY-6 and ring C is C-4, a compound wherein R ⁴ and R ⁸ are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-4 and R ⁹ and R 8 ¹⁰ are R910-4, X, Y, X 'and Y' are XY-6 and ring C is C-6, a compound wherein R ⁴ and R ⁸ are R 45-3, R ® and R ⁷ are R67-1, R ⁸ and R ¹¹ are R 811-4 and R ⁹ and R ¹⁰ are R 910-4, X, Y, X 'and Y' are XY-6 and ring C is C-9, a compound wherein R ⁴ and R ⁸ are R45-3, R® and ^R7 are R67-1, R® and ^R11 are R811-4 and ^R9 and ^R10 are R910-4, X, Y, X 'and Y' are XY-9 and the ring C is C-4, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ⁶ are R 811-4 and R ⁹ and R ¹⁰ are R 910-4, X, Y, X 'and Y' are XY-9 and ring C is C-6, a compound wherein R ⁴ and R ⁸ are R 45-3, R ® and R ⁷ are R67-1, R ® and R ⁶ are R811-4 and R ⁹ and R ¹⁰ are R 910-4, X, Y, X 'and Y' are XY-9 and ring C is C-9, a compound wherein R ⁴ and R ⁸ are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R 811-4 and R ⁹ and R ¹⁰ are R 8 910-4, X, Y, X 'and Y' are XY-17 and ring C is C-4, a compound wherein R ⁴ and R ⁸ are R 45-3, R ® and R ⁷ are R67-1, R ® and R 8 are R 811-4 and R ⁹ and R ¹⁰ are R 910-4, X, Y, X 'and Y' are XY-17 and ring C is C-6, a compound wherein R ⁴ and R ⁸ are R 45- 3 R® and ^R7 are R67-1, R® and R are R811-4 and ^R9 and ^R10 are R910-4, X, Y, X 'and Y' are XY-17 and C ring is C -9, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ⁶ are R 811-4 and R ⁹ and R ¹⁰ are R 910-5, X, Y, X 'and Y' are XY-5 and ring C is C-4, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R 67-1, R ⁸ and are R 811-4 and R ⁹ and R ¹⁰ are R 910-5, X, Y, X 'and Y' are XY-5 and ring C is C-6, a compound wherein R ⁴ and R ⁸ are R 45-3, R ® and R ⁷ are R 67- 1, R ® and R ¹¹ are R 811-4 and R ⁹ and R ¹⁰ are R 910-5, X, Y, X 'and Y' are XY-5 and ring C is C-9, a compound wherein R ⁴ and R ⁸ are R45-3, R® and ^R7 are R67-1, ^R8 and R ^ are R811-4 and ^R9 and ^R10 are R910-5, X, Y, X 'and Y' are XY-6 and ring C is C-4, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁶ and R ⁷ are R 6 7-1, R ⁸ and R ^ are R811-4 and ^R9 and ^R10 are R910-5, X, Y, X 'and Y' are XY-6 and C ring is C-6,

AND

a compound wherein R ⁴ and R ⁸ are R45-3, ^R8 and ^R7 are R67-1, ^R8 and R ^ are R811-4 and ^R9 and ^R10 are R910-5, X, Y, X 'and Y are XY-6 and ring C is C-9, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-4 and R ⁹ and R 8 ¹⁰ are R910-5, X, Y, X 'and Y' are XY-9 and ring C is C-4, a compound wherein R ⁴ and R ⁵ are R 45-3, R ⁸ and R ⁷ are R67-1, R ⁸ and R ¹¹ are R 811-4 and R ⁹ and R ¹⁰ are R 910-5, X, Y, X 'and Y' are XY-9 and ring C is C-6, a compound wherein R ⁴ and R ⁸ are R45-3, ^R8 and ^R7 are R67-1, ^R8 and ^R11 are R811-4 and ^R9 and ^R10 are R910-5, X, Y, X 'and Y' are XY-9 and C ring is C-9, a compound wherein R ⁴ and R ⁸ are R45-3, ^R8 and ^R7 are R67-1, ^R8 and R ^ are R811-4 and ^R9 and ^R10 are R910-5, X, Y, X 'and Y' are XY-17 and C ring is C-4, a compound wherein R ⁴ and R ⁸ are R45-3, ^R8 and ^R7 are R67-1, ^R8 and R ^ are R811-4 and R ⁹ and R ¹⁰ are R 910-5, X, Y, X 'and Y' are XY-17 and ring C is C-6, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R67-1, ^R8 and ^R11 are R811-4 and ^R9 and ^R10 JSO for R910-5, X, Y, X 'and Y' are XY-17 and ring C is C-9, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R67-1, R ⁸ and R ¹¹ are R 811-4 and R ⁹ and R ¹⁰ are R 910-7, X, Y, X 'and Y' are XY-5 and ring C is C-4, the compound wherein R ⁴ and R ⁸ are R 45 -3, R ⁸ and R ⁷ are R67-1, ^R8 and R ^ are R811-4 and ^R9 and ^R10 are R910-7, X, Y, X 'and Y' are XY-5 and C ring is C -6, a compound wherein R ⁴ and R ⁸ are R45-3, ^R8 and ^R7 are R67-1, ^R8 and R ^ are R811-4 and ^R9 and ^R10 are R910-7, X, Y, X 'and Y' are XY-5 and ring C is C-9, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ⁸ are R 811-4 and R ^{8 9} and R ¹⁰ are R 910-7, X, Y, X 'and Y' are XY-6 and ring C is C-4, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R67 -1, ^R8 and ^R11 are R811-4 and ^R9 and ^R10 are R910-7, X, Y, X 'and Y'jsou XY-6 and C ring is C-6, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ⁴¹ are R 811-4 and R ⁹ and R ¹⁰ are R 910-7, X, Y, X 'and Y' are XY- 6 and ring C is C-9, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R67-1, ^R8 and R ^ are R811-4 and ^R9 and ^R10 are R910-7, X, Y, X 'and Y' are XY-9 and C ring is C-4 • · fc · 4, fcfc, fcfc 9, fcfc 9, fcfc 9, where R ⁴ and R ® are R45 -3 R® and ^R7 are R67-1, ^R8 and R ^ are R811-4 and ^R9 and ^R10 are R910-7, X, Y, X 'and Y' are XY-9 and C ring is C-6, a compound wherein R ⁴ and R ⁵ are R 45-3, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-4 and R ⁹ and R ¹⁰ are R 910-7, X, Y , X 'and Y' are XY-9 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-4 and R ⁹ and R ⁰ are R910-7, X, Y, X 'and Y'jsou XY-17 and C ring is C-4, a compound wherein R ⁴ and R® are R45-3, R® and R ⁷ are R67-1, R® and ^R11 are R811-4 and ^R9 and ^R10 are R910-7, X, Y, X 'and Y' are XY-17 and C ring is C-6, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ^ ¹ are R811-4 and R ⁹ and R ¹⁰ are R910-7, X, Y, X 'and Y' are XY-17 and ring C is C-9; wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R 67-1, R ® and R ⁶ are R 811-5 and R ⁹ and R ¹⁰ are R 910-5, X, Y, X 'and Y 'are XY-7 and ring C is C-4, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-8 and R ⁹ and R ¹⁰ are R 910-4, X, Y, X 'and Y' are XY-5 and ring C is C-4, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1 , R ⁸ and R ⁸ are R 811-8 and R ⁹ and R ¹⁰ are R 910-4, X, Y, X 'and Y' are XY-5 and ring C is C-6, a compound wherein R ⁴ and R ⁸ are R45-3, R® and ^R7 are R67-1, ^R8 and R ^ are R811-8 and ^R9 and ^R10 are R910-4, X, Y, X 'and Y' are XY-5 and the ring C is C-9, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ⁶ are R 811-8 and R ⁹ and R ¹⁰ are R 910-4, X , Y, X 'and Y' are XY-6 and ring C is C-4, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and are R811-8 and R ⁹ and R ¹⁰ are R 910-4, X, Y, X 'and Y' are XY-6 and ring C is C-6, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, ^R8 and ^R11 are R811-8 and ^R9 and ^R10 are R910-4, X , Y, X 'and Y' are XY-6 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ⁸ and R ⁶ are R 811 -8 and R ⁹ and R ¹⁰ are R 910-4, X, Y, X 'and Y' are XY-9 and ring C is C-4, a compound wherein R ⁴ and R ® are R 45-3, R ® and ^R7 are R67-1, R® and RV are R811-8 and ^R9 and ^R10 are oxytocic R910-4, X, Y, X 'and Y' are XY-9 and C ring is C-6,

a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ** ¹ are R811-8 and R ⁹ and R 8 ® are R910-4, X, Y, X 'and Y' are XY-9 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-8 and R ⁹ and R ¹⁰ are R 910-4, X, Y, X 'and Y' are XY-17 and ring C is C-4, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R67-1, R® and R ¹ are R811-8 and ^R9 and ^R1 ® are R910-4, X, Y, X 'and Y'jsou XY-17 and C ring is C-6, compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-8 and R ⁹ and R ⁹ ® are R910-4, X, Y, X 'and Y are XY-17 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-8 and R ⁹ and R 7 ¹ ® are R910-5, X, Y, X 'and Y' are XY-5 and ring C is C-4, a compound wherein R ⁴ and R ® are R45-3, R ® and R ⁷ are R67-1 , R ® and R ⁶ are R 811-8 and R ⁹ and R ¹ ® are R 910-5, X, Y, X 'and Y' are XY-5 and ring C is C-6, a compound wherein R ⁴ and R ⁸ are R45-3, R® and ^R7 are R67-1, R® and R @ ¹ are R811-8 and R ⁹ and R ¹ ® are R 910-5, X, Y, X 'and Y' are XY-5 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R® and ^R11 are R811-8 and ^R9 and ^R1 ® are R910-5, X, Y, X 'and Y' are XY-6 and C ring is C-4, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-8 and R ⁹ and R ¹ ® are R910-5, X, Y, X 'and Y' are XY-6 and ring C is C-6, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ⁶ are R811-8 and R ⁹ and R ¹ ® are R910-5, X, Y, X 'and Y' are XY-6 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ®aR ^ are R811-8 and ^R9 and ^R1 ® are R910-5, X, Y, X 'and Y' are XY-9 and C ring is C-4, a compound wherein ^R4 and R45 are R® -3 R® and ^R7 are R67-1, R® and ^R11 are R811-8 and ^R9 and ^R1 ® are R910-5, X, Y, X 'and Y' are XY-9 and C ring is C-6, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ⁶ are R811-8 and R ⁹ and R ¹⁰ are R910-5, X , Y, X 'and Y' are XY-9 and ring C is C-9, a compound wherein R ⁴ and R ⁴ ® are R45-3, R ® and R ⁷ are R67-1, R ® and R ¹ ^ are R811-8 and R ⁹ and R ¹ ® are R910-5, X, Y, X 'and Y' are XY- 17 and ring C is a C-4 compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ⁸ and R ¹¹ are R 811-8 and R ⁹ and R ¹⁹ are R 910-5, X, Y, X 'and Y' are XY-17 and ring C is C-6, the compound wherein R ⁴ and R ⁸ are R45-3, R® and ^R7 are R67-1, R® and ^R11 are R811-8 and ^R9 and ^R19 are R910-5, X, Y, X 'and Y' are XY-17 and C ring is C-9, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-8 and R ⁹ and R ¹⁹ are R910-7, X, Y, X 'and Y' are XY-5 and ring C is C-4, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R 811- 8 and R ⁹ and R ¹⁹ are R 910-7, X, Y, X 'and Y' are XY-5 and ring C is C-6, a compound wherein R ⁴ and R ® are R 45-3, R ® and R 8 ⁷ are R67-1, R® and ^R11 are R811-8 and ^R9 and ^R19 are R910-7, X, Y, X 'and Y' are XY-5 and C ring is C-9, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R 67-1, R ® and R ¹¹ are R 811-8 and R ⁹ and R ¹⁹ are R 910-7, X, Y, X 'and Y' are XY-6 and ring C is C-4, a compound wherein R ⁴ and R ® are R 45- 3 R® and ^R7 are R67-1, R® and ^R11 are R811-8 and ^R9 and ^R19 are R910-7, X, Y, X 'and T are XY-6 and C ring is C 6, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-8 and R ⁹ and R ¹⁹ are R910-7, X, Y, X 'and Y' are XY-6 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-8 and R 7 ⁹ and R ¹⁹ are R 910-7, X, Y, X 'and Y' are XY-9 and ring C is C-4, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67 -1, R ® and R ¹¹ are R 811-8 and R ⁹ and R ¹⁹ are R 910-7, X, Y, X 'and Y' are XY-9 and ring C is C-6, a compound wherein R ⁴ and R® are R45-3, R® and ^R7 are R67-1, R® and ^R11 are R811-8 and ^R9 and ^R19 are R910-7, X, Y, X 'and Y' are XY-9 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-8 and R ⁹ and R ¹⁹ are R910-7 X, Y, X 'and Y' are XY-17 and ring C is C-4 compounds and, wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-8 and R ⁹ and R ¹⁹ are R910-7, X, Y, X 'and Y 'are XY-17 and ring C is C-6, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-8 and R ⁹ and R ¹⁹ is R910-7, X, Y, X 'and Y' are XY-17 and ring C is C-9, 00 000000 0 00 0 000

000 00 00 0

0 0 0

0 0 0

A compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R 67-1, R ⁸ and R ¹¹ are R 811-10 and R ⁹ and R ¹⁰ are R 910-4, X, Υ, X 'and Y' are XY-5 and ring C is C-4, a compound wherein R ⁴ and R ⁸ are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R 7 ⁹ and R ¹⁰ are R 910-4, X, Υ, X 'and Y' are XY-5 and ring C is C-6, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁷ and R ⁷ are R67 -1, R ® and R ¹¹ are R 811-10 and R ⁹ and R ¹⁰ are R 910-4, X, Υ, X 'and Y' are XY-5 and ring C is C-9, a compound wherein R ⁴ and R ⁸ are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R ¹⁰ are R910-4, X, Υ, X 'and Y' are XY-6 and ring C is C-4, a compound wherein R ⁴ and R ⁸ are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R ¹⁰ are R910-4 , X, Υ, X 'and Y' are XY-6 and ring C is C-6, a compound wherein R ⁴ and R ⁸ are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and ^R9 and ^R10 are R910-4, X, Υ, X 'and Y' are XY-6 and C ring is C-9, a compound wherein R ⁴ and R ⁸ are R45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R 811-10 and R ⁹ and R ¹⁰ are R 910-4, X, Υ, X 'and Y' are XY-9 and ring C is C-4, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R67-1, R ® and R ¹¹ are R 811-10 and R ⁹ and R ¹⁰ are R 910-4, X, Υ, X 'and Y' are XY-9 and ring C is C-6, the compound wherein R ⁴ and R ⁸ are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R ¹⁰ are R910-4, X, Υ, X 'and Y are XY-9 and ring C is C-9, a compound wherein R ⁴ and R ⁸ are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R 8 ¹⁰ are R910-4, X, Υ, X 'and Y' are XY-17 and ring C is C-4, a compound wherein R ⁴ and R ⁸ are R 45-3, R ® and R ⁷ are R67-1, R ⁸ and R ¹¹ are R 811-10 and R ⁹ and R ¹⁰ are R 910-4, X, Υ, X 'and Y' are XY-17 and ring C is C-6, the compound wherein R ⁴ and R ⁸ are R45-3, R® and ^R7 are R67-1, R® and ^R11 are R811-10 and ^R9 and ^R10 are R910-4, X, Υ, X 'and Y'jsou XY-17 and C ring is C-9, a compound wherein R ⁴ and R ⁸ are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R ¹⁰ are R910-5, X, Υ, X 'and Y' are XY-5 and ring C is C-4, mp antifungal compound, wherein R ⁴ and R ⁸ are R45-3, R® and ^R7 are R67-1, R® and ^R11 are R811-10 and ^R9 and ^R10 are R910-5, X, Υ, X 'and Y 'are XY-5 and ring C is C-6,

Ftft compound where R ⁴ and R ® are R45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ® and R ¹⁰ are R 910-5, X, Y, X 'and Y' are XY-5 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R® and ^R11 are R811-10 and R® and ^R10 are R910-5, X, Y, X 'and Y' are XY-6 and C ring is C-4, a compound wherein R ⁴ and R ® are R45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ® and R ¹⁰ are R910-5, X, Y, X 'and Y' are XY -6 and ring C is C-6, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ® and R ¹⁰ are R910 -5, X, Y, X 'and Y' are XY-6 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and ^R11 are R811-10 and R® and ^R10 are R910-5, X, Y, X 'and Y' are XY-9 and C ring is C-4, a compound wherein R ⁴ and R45-3 are R® , R® and ^R7 are R67-1, R® and ^R11 are R811-10 and R® and ^R10 are R910-5, X, Y, X 'and Y' are XY-9 and C ring is C 6, a compound wherein R R® and ⁴ are R45-3, R® and ^R7 are R67-1, R® and ^R11 are R811-10 and R® and ^R10 are R910-5, X, Y, X 'and Y' are XY -9 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ® and R ¹⁰ are R910 -5, X, Y, X 'and Y' are XY-17 and ring C is C-4, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and ^R11 are R811-10 and R® and ^R10 are R910-5, X, Y, X 'and Y' are XY-17 and C ring is C-6, a compound wherein R ⁴ and R45-3 are R® , R® and ^R7 are R67-1, R® and ^R11 are R811-10 and R® and ^R10 are R910-5, X, Y, X 'and Y' are XY-17 and C ring is C 9, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ® and R ¹⁰ are R910-5, X, Y, X 'and Y' are XY-20 and ring C is C-4, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R 7 ® and ^R10 are R910-5, X, Y, X 'and Y' are XY-20 and C ring is C-6, a compound wherein R ⁴ and R® are R45-3, R® and ^R7 is R67 -1 R® and ^R11 are R811-10 and R ¹⁰ R® and JSO for R910-5, X, Y, X 'and Y' are XY-20 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ® and R ¹⁰ are R910-7, X, Y, X 'and Y' are XY-5 and ring C is C-4,

4444

4 4

4 4 4

4 4

444

4

4 4 4

4 4

4 4

4 a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R 67-1, R ® and R ¹¹ are R 811-10 and R ⁹ and R ¹⁰ are R 910-7, X, Y, X ' and Y 'are XY-5 and ring C is C-6, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and ^R10 are R910-7, X, Y, X 'and Y' are XY-5 and C ring is C-9, a compound wherein R ⁴ and R® are R45-3, R® and ^R7 is R67- 1 R® and ^R11 are R811-10 and ^R9 and ^R10 are R910-7, X, Y, X 'and Y' are XY-6 and C ring is C-4, a compound wherein R ⁴ and R ® are R45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R ¹⁰ are R910-7, X, Y, X 'and Y' are XY-6 and ring C is C-6, the compound wherein R ⁴ and R ® are R45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R ¹⁰ are R910-7, X , Y, X 'and Y' are XY-6 and ring C is C-9, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811 -10 and R ⁹ and R ¹⁰ are R 910-7, X, Y, X 'and Y' are XY-9 and ring C is C-4, a compound wherein R ⁴ and R ® are R 45-3, R ® and ^R7 are R67-1, R® and ^R11 are R811-10 and R ⁹ and R ¹⁰ are R910-7, X, Y, X 'and Y' are XY-9 and C ring is C-6, a compound wherein R ⁴ and R® are R45-3, R® and ^R7 is R67 -1 R® and ^R11 are R811-10 and ^R9 and ^R1 ® are R910-7, X, Y, X 'and Y' are XY-9 and C ring is C-9, a compound wherein R ⁴ R® and are R45-3, R® and ^R7 are R67-1, R® and ^R11 are R811-10 and ^R9 and ^R10 are R910-7, X, Y, X 'and Y' are XY- 17 and ring C is C-4, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R ¹⁰ are R910- 7, X, Y, X 'and Y' are XY-17 and ring C is C-4, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and ^R9 and ^R10 are R910-7, X, Y, X 'and Y' are XY-17 and C ring is C-6, a compound wherein R ⁴ and R® are R45-3, R® and ^R7 are R67-1, R® and ^R11 are R811-10 and ^R9 and ^R10 are R910-7, X, Y, X 'and Y' are XY-17 and C ring is C-9 , the compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R ¹⁰ are R910-7, X, Y, X ' and Y 'are XY-20 and ring C is C-4, a compound wherein R ⁴ and R ® are R45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R ¹⁰ are R910-7, X, Y, X 'and Y' are XY-20 and ring C is C-6, φ · · φ φ φ • • • • φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ kde kde kde φ φ φ φ φ φ · ⁴ and R ⁵ are R 45-3, R ® and R ⁷ are R67-1, R ® and R ¹¹ are R811-10 and R ⁹ and R ¹⁰ are R910-7, X, Y, X 'and Y' are XY -20 and ring C is C-9, a compound wherein X 'is -O-, -NR 6 - or -S (O) p - and ring C is an optionally substituted five-membered heterocycle containing one or two heteroatoms, wherein ring C is a pyrimidine ring, one of XY and -X'-Y 'is 1-pyrrolidinyl, 1-piperidinyl, 4-morphinyl, 4-thiomorphinyl, optionally substituted 1-piperadinyl (wherein the substituents are lower alkyl or lower alkenyl) or optionally substituted 1 -pyrolyl (wherein the substituents are lower alkyl) and the other is -NHCH 2 CH = CMe 2, -OCH 2 CH = CMe 2, or -SCH 2 CH = CMe 2, a compound when e ring C is a pyridine ring, one of -XY and -X'-Y 'is 1-pyrrolidinyl, optionally substituted 1-pyrrolyl (where the substituents are lower alkyl) and the other is NHCH 2 CH = CMe 2, -OCH 2 CH = CMe 2 or -SCH 2 CH = Another embodiment of the present invention is [2] a compound of the general formula:

wherein each symbol corresponds to the definition given above in [1], [3] a compound of the general formula Ia ':

9 9 9 9 9 9 9 9 9 9 9 99 9 9 9 9

9 • • 9

wherein ring B is an optionally substituted 5- or 6-membered heterocycle containing one or two heteroatoms (wherein the substituent is halogen, hydroxyl, optionally substituted lower alkyl, optionally substituted lower alkoxy, optionally substituted lower alkenyl, optionally substituted lower alkenyloxy, optionally substituted acyloxy, carboxyl , optionally substituted lower alkoxycarbonyl, optionally substituted lower alkenyloxycarbonyl, optionally substituted lower alkylthionyl, optionally substituted lower alkenylthionyl, optionally substituted amino, guanidine, nitro, optionally substituted lower alkylsulfonyl, optionally substituted lower alkylsulfonyloxy, optionally substituted with aryls, optionally substituted with aryls compounds where ring B is substituted only by halogen (halogens) and represents a bond when ring B is five-membered h eterocycle,

X, X ', Y and Y' are the same as defined in [1],

R ¹ together with Y and Y 'form - (CH ₂ ) m -, - (CH ₂ ) 2 -Q- (CH ₂ ) 2 - (wherein Q is CH ₂ , O, S or NR'), -CR '= CH-CH = CR'-, -CH = N-CH = CH-, -N = CH-N = CH-, -C (= O) -O (CH ₂ ) n -, C (= O) -NR '- (CH ₂ ) N- or -C (= O) -NR'-N = CH-, wherein m is 4 or 5, n is 2 or 3,

R 'is hydrogen or lower alkyl or lower alkenyl,

Y is optionally substituted lower alkoxy when X is -CH ₂ -,

Y 'is optionally substituted lower alkoxy when X' is -CH ₂ -,

Y is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl or optionally substituted lower arylsulfonyl when X is -O- or -NR ¹ -, Y 'is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl, or optionally substituted lower arylsulfonyl when X' is -O- or -NR ¹ -,

Y is hydrogen or halogen when X is -CH ₂ - or -NR ¹ -,

Y 'is hydrogen or halogen when X' is -CH ₂ - or -NR ¹ -;

49

9 4 4

4 4 4

4 4 4

44

Φ »* • · Φ 9

444 9 • Φ • · 4 4 4 φφφ φφ

4

R ⁴ , R ⁸ , R ⁸ , R ⁷ , R ¹² , R ¹⁸ , R ¹⁴ and R ¹⁸ are independently hydrogen, halogen, hydroxyl, optionally substituted lower alkyl, optionally substituted lower alkoxy, optionally substituted lower alkenyl, optionally substituted lower alkenyloxy, optionally substituted acyloxy, carboxyl, optionally substituted lower alkoxycarbonyl, optionally substituted lower alkenyloxycarbonyl, optionally substituted lower alkylthionyl, optionally substituted lower alkenylthionyl, optionally substituted amino, optionally substituted carbamoyl, guanidine, lower alkyl, optionally substituted, optionally substituted, alkylsulfonyloxy, optionally substituted arylsulfonyl or optionally substituted arylsulfonyloxy, except (i) a compound wherein Y and Y 'are simultaneously hydrogen, (ii) a compound wherein at least one of Y and Y' is optionally substituted acyl, (iii) a compound, wherein at least one of -XY and -X'-Y 'is unsubstituted lower alkoxy, and (iv) compounds wherein -XY and -XY' are simultaneously optionally substituted lower alkoxy or amino substituted phenyl, a salt thereof or a hydrate thereof. The following compounds Ia ', salts or hydrates thereof are more preferred.

a compound wherein R ⁴ and R ⁸ are R 45-1, a compound wherein R ⁴ and R ⁸ are R 45-2, a compound wherein R ⁴ and R ⁸ are R 45-3, a compound wherein R ⁴ and R ⁸ are R 45- 4, a compound wherein R ⁴ and R ⁸ are R 45-5, a compound wherein R ⁴ and R ⁸ are R 45-6, a compound wherein R ⁴ and R ⁸ are R 45-7, a compound wherein R ⁸ and R ⁷ are R67-1, a compound wherein R ⁸ and R ⁷ are R67-2, a compound wherein ring B is a 5- or 6-membered heterocycle containing at least one nitrogen atom (hereinafter referred to as "ring B is Β-Γ)", wherein ring B is a six-membered heterocycle containing at least one nitrogen atom (hereinafter referred to as "ring B is B-2"),

9444

94

9 * ·· *

4

443 44 9

4 4 4

44 94 44

4 4 · · 9 9 • «9 ·

99 compound wherein ring B is optionally substituted pyridine, optionally substituted pyrimidine, optionally substituted pyridazine or optionally substituted pyrazine (hereinafter referred to as "ring B is B-3"), compound wherein ring B is optionally substituted pyridine or optionally substituted pyrimidine (hereinafter referred to as "ring B is B-4"), a compound wherein ring B is optionally substituted pyridine or optionally substituted pyrimidine (wherein the substituents are optionally substituted lower alkyl or optionally substituted lower alkoxy) (hereinafter referred to as "ring B" is B-5 "), a compound wherein Ring B is an optionally substituted pyridine wherein" ring B is B-6 "), a compound wherein Ring B is

R ⁸

R ¹¹ where G is CH or N, R ⁸ and R ¹¹ are independently halogen, hydroxyl, optionally substituted lower alkyl, optionally substituted lower alkoxy, optionally substituted lower alkenyl, optionally substituted lower alkenyloxy, optionally substituted acyloxy, carboxyl or optionally substituted lower alkoxycarbonyl (hereinafter referred to as "ring B is B-7"), a compound wherein R ¹² , R ¹³ , R ¹⁴ and R ¹⁸ are independently hydrogen, hydroxyl, halogen, optionally substituted lower alkoxy, optionally substituted acyloxy, optionally substituted lower alkylsulfonyloxy or optionally substituted arylsulfonyloxy (hereinafter referred to as "R ¹² , R ¹³ R ¹⁴ , R ¹⁵ and R ¹⁶ are R 12-15-1"), a compound wherein R ¹ , R ² , R ³ , R ⁴ and R @ ⁸ are independently hydrogen, hydroxy, halogen, lower alkoxy, acyloxy, optionally substituted lower alkylsulphonyloxy or arylsulfonyloxy (hereinafter denoted as "R ^2, R ^3, R (R ⁴ and R ¹⁸ are R 12-15-2 "), a compound wherein R ¹² , R ¹³ , R ¹⁴ and R ¹⁸ independently of one another are hydrogen, halogen or lower alkyl (hereinafter referred to as" R ¹² , R ¹³ , R ¹⁴ and R ¹⁸ are R 12-15-3 "), a compound wherein R ^ ² , R ^ ³ , R ^ ⁴ and R ^ ⁸ are independently hydrogen, chlorine or fluorine (hereinafter referred to as" R ^ ² ") , R ^ ³ , R ^ ⁴ and R ^ ⁸ are R12-15-4 "), a compound wherein X, Y, X 'and Y' are XY-1, wherein X, Y, X 'and Y' are XY-2, a compound wherein X, Y, X 'and Y' are XY-3, a compound wherein X, Y, X 'and Y' are XY-4, a compound wherein X, Y, X 'and Y' are XY-5, a compound wherein X, Y, X 'and Y' are XY-6, a compound wherein X, Y, X 'and Y' are XY-7, a compound wherein X, Y, X 'and Y' are XY-8, a compound wherein X, Y, X 'and Y' are XY-9, a compound wherein X, Y, X 'and Y' are XY-10 , a compound wherein X, Y, X 'and Y' are XY-11, a compound wherein X, Y, X 'and Y' are XY-12, a compound wherein X, Y, X 'and Y' are XY- 13, a compound wherein X, Y, X 'and Y' are XY-14, compound wherein X, Y, X 'and Y' are XY-15, a compound wherein X, Y, X 'and Y' are XY-16, a compound wherein X, Y, X 'and Y' are XY-17 , a compound wherein X, Y, X 'and Y' are XY-18, a compound wherein X, Y, X 'and Y' are XY-19, a compound wherein X, Y, X 'and Y' are XY- 20, a compound wherein R ⁴ and R ⁸ are R 45-3 and R ⁸ and R ⁷ are R 67-2, a compound wherein R ⁴ and R ⁸ are R 45-4 and R ⁸ and R ⁷ are R 67-2, the compound, wherein R ⁴ and R ⁸ are R 45-4 and ring B is B-1, a compound wherein R ⁴ and R ⁸ are R 45-4 and ring B is B-2, a compound wherein R ⁴ and R ⁸ are R45-4 and ring B is B-4 compound wherein R ⁴ and R ⁸ are R45-4 and R ^2, R 13, R14 _and R15 _sum f j 2-15-3 compound wherein R ⁴ and R ⁸ are R45-1 R ⁸ and R ⁷ are R67-1, R ^2, R13, R14 _and R15 _sum j R12-15-2, B ring is B-3 and X, X ', Y and Y' are XY-6, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ¹² , R ¹³ , R ¹⁴ and R ¹⁸ are R 12-15-2, ring B is B-3 and X, X ' , Y and Y 'are XY-17, a compound wherein R ⁴ and R ⁸ are R 45-1, R ⁸ and R ⁷ are R 67-1, R ^ ² , R ^ ³ , R ^ and R ^ ⁸ are

R12-15-2, ring B is B-5 and X, X ', YaY' are XY-6,

a compound wherein R ⁴ and R® are R45-1, R® and ^R7 are R67-1, ^{R12, R13, R14} and ^R1 ® are R12-15-2, B ring is B-5 and X , X ', Y and Y' are XY-17, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R 67-1, R ^ ² , R ^ ³ , R ^ ⁴ and R ¹ ® are R12-15-2, ring B is B-7 and X, X ', YaY' are XY-6, a compound wherein R ⁴ and R ® are R45-1, R ® and R ⁷ are R67-1, R ¹² , R ¹³ , R ¹⁴ and R ¹¹ are R 12-15-2, ring B is B-7 and X, X ', Y and Y' are XY-17, the compound wherein R ⁴ and R ® are R 45 -1 R® and R ⁷ are R67-1, R ^2, R ^3, R ⁴ and R ¹ ® are R12-15-3, B ring is B-3 and X, X ', Y and Y are XY-6, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ¹² , R ¹³ , R ¹⁴ and R ¹ ® are R12-15-3, ring B is B-3 and X, X ', YaY' are XY-17, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ¹² , R ¹³ , R ¹⁴ and R ¹ ® are R12-15-3, ring B is B-5 and X, X ', YaY' are XY-6, a compound wherein R ⁴ and R ® are R45-1, R ® and R ⁷ are R67-1 , R ^ ² , R ^ ³ , R ^ ⁴ and R ^ ® are R12-15-3, ring B is B-5 and X, X ', Y and Y'is XY-17, the compound wherein R ⁴ and R ® are R45-1, R ® and R ⁷ are R67-1, R ¹² , R ¹³ , R ¹⁴ and R ¹ ® are R12-15-3, ring B is B -7 and X, X ', YaY' are XY-6, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R 67-1, R ^ ² , R ^ ³ , R ^ ⁴ and R ¹ ® are R 12-15-3, ring B is B-7 and X, X ', YaY' are XY-17, the compound wherein R ⁴ and R ® are R45-1, R ® and R ⁷ are R67- 1, R ¹² , R ¹³ , R ¹⁴ and R ¹ ® are R 12-15-4, ring B is B-3 and X, X ', YaY' are XY-6, a compound wherein R ⁴ and R ® are R 45 -1 R® and ^R7 are R67-1, ^{R12, R13, R14} and ^R1 ® are R12-15-4, B ring is B-3 and X, X ', Y and XY Y'jsou -17, a compound wherein R ⁴ and R ® are R45-1, R ® and R ⁷ are R67-1, R ¹² , R ¹³ , R ¹⁴ and R ¹ ® are R12-15-4, ring B is B- 5 and X, X ', YaY' are XY-6, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R 67-1, R ^ ² , R ^ ³ , R ^ ⁴ and R ^ ® are R12-15-4, ring B is B-5 and X, X ', YaY' are XY-17, a compound wherein R ⁴ and R ® are R45-1, R ® and R ⁷ are R67-1 , R ¹² , R ¹³ , R ¹⁴ and R ¹ ® are R12-15-4, ring B is B-7 and X, X ', YaY' are XY-6, a compound wherein R ⁴ and R ® are R 45-1, R ® and R ⁷ are R67-1, R ¹² , R ¹³ , R ¹⁴ and R ¹ ® are

R12-15-4, ring B is B-7 and X, X ', YaY' are XY-17,

a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R 67-1, R ¹² , R ¹³ , R ¹⁴ and R ¹⁸ are R 12-15-2, ring B is B-3 and X, X ', Y and Y' are XY-6, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R 67-1, R ¹² , R ¹³ , R ¹⁴ and R ¹⁸ are R ¹² - 15-2, ring B is B-3 and X, X ', Y and Y' are XY-17, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R67-1, R ¹² , R ¹³ , R ¹⁴ and R ¹⁸ are R 12-15-3, ring B is B-4 and X, X ', Y and Y' are XY-6, the compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R67-1, R ^2, R ^3, R ⁴ and R ⁸ are R12-15-2, B ring is B-5 and X, X ', Y and XY Y'jsou -6, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R 67-1, R ¹² , R ¹³ , R ¹⁴ and R ¹⁸ are R 12-15-2, ring B is B-5 and X, X ', Y and Y' are XY-17, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R 67-1, R ¹² , R ¹³ , R ¹⁴ and R ¹⁸ are R12-15-2, ring B is B-7 and X, X ', Y and Y' are XY-6, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R67-1, R ¹² , R ¹³ , R ¹⁴ and R ¹⁸ are R 12-15-2, ring B is B-7 and X, X ', Y and Y' are XY-17, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R 67-1, R ¹² , R ¹³ , R ¹⁴ and R ¹⁸ are R 12-15-3, ring B is B-3 and X, X ', Y and Y' are XY-6, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R 67-1, R ^ ² , R ^ ³ , R ¹⁴ and R ¹⁸ are R 12 -15-3, ring B is B-3 and X, X ', Y and Y' are XY-17, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R67-1, R ^ ² , R ^ ³ , R ^ ⁴ and R ^ ⁸ are R12-15-3, ring B is B-5 and X, X ', Y and Y' are XY-5, a compound wherein R ⁴ and R ⁸ are R45-3, ^R8 and ^R7 are R67-1, ^{R12, R13, R14} and ^R18 are R12-15-3, B ring is B-5 and X, X ', Y and Y'jsou XY-6, the compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R 67-1, R ^ ² , R ^ ³ , R ^ ⁴ and R ^ ⁸ are R12-15-3, a ring B is B-5 and X, X ', Y and Y' are XY-7, a compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R 67-1, R ^ ² , R ^ ³ , R ⁴ and R ⁸ are R 12-15-3, ring B is B-5 and X, X ', Y and Y' are XY-17, the compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R 67-1, R ¹² , R ¹³ , R ¹⁴ and R ¹⁸ are R 12-15-3, ring B is B-7 and X, X ', Y and Y' are XY-6; the compound wherein R ⁴ and R ⁸ are R 45-3, R ⁸ and R ⁷ are R 67-1, R ^ ² , R ^ ³ , R ^ ⁴ and R ^ ⁸ are

R12-15-3, ring B is B-7 and X, X ', Y and Y'is XY-17, · · ····· · · · · · · ··· A compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ¹² , R ¹³ , R ¹⁴ and R ¹ ® are R12 -15-4, ring B is B-3 and X, X ', Y and Y' are XY-6, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ¹² , R ¹³ , R ¹⁴ and R ¹¹ are R 12-15-4, ring B is B-3 and X, X ', Y and Y' are XY-17, the compound wherein R ⁴ and R ® are R 45- 3 R® and ^R7 are R67-1, ^{R12, R13, R14} and ^R1 ® are R12-15-4, B ring is B-5 and X, X ', Y and Y' are XY-6 a compound wherein R ⁴ and R® are R45-3, R® and ^R7 are R67-1, ^{R12, R13, R14} and ^R1 ® are R12-15-4, B ring is B-5 and X, X ', Y and Y' are XY-17, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ¹² , R ¹³ , R ¹⁴ and R ¹ ® are R12-15-4, ring B is B-7 and X, X ', Y and Y' are XY-6, a compound wherein R ⁴ and R ® are R 45-3, R ® and R ⁷ are R67-1, R ¹² , R ¹³ , R ¹⁴ and R ¹ ® are R 12-15-4, ring B is B-7 and X, X ', Y and Y 'are XY-17, a compound wherein ring B is B-7 and X and X' are independently -O-, -NR ¹ - (wherein R ¹ is hydrogen, lower alkyl, lower alkenyl or lower alkylcarbonyl) or -S (O) p-, where p is an integer from 0 to 2,

Another embodiment of the present invention is [4] a compound of the general formula If ':

wherein one of rings B and C is an optionally substituted five or six membered heterocycle containing one or two heteroatoms and the other is a six membered heterocycle containing at least one nitrogen atom, with the exception of a compound wherein each ring B substituent is cyano or halogen,

X, X ', Y, Y' and W ³ are the same as defined in [1] and W ² is the same as defined in [3],

R 1 together with Y and Y 'form - (CH 2) m -, - (CH ₂ ) 2 -Q- (CH ₂ ) 2 - (wherein Q is CH 2, O, S or NR'), -CR '= CH- CH = CR'-, -CH = N-CH = CH-, -N = CH-N = CH-, -C (= O) -O (CH ₂ ) n -, -C (= O) NR'- _(CH2) n- or -C (= O) -NR'-N = CH- wherein m is 4 or 5, n is 2 or 3 and

R 'is hydrogen, lower alkyl or lower alkenyl,

Y is optionally substituted lower alkoxy when X is -CH 2 -,

Y 'is an optionally substituted lower alkoxy when X' is -CH 2 -,

Y is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl or optionally substituted lower arylsulfonyl when X is -O- or -NR ¹ -, Y 'is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl, or optionally substituted lower arylsulfonyl when X' is -O- or -NR ¹ -,

Y is hydrogen or halogen when X is -CH ² - or -NR ¹ -,

Y 'is hydrogen or halogen when X' is -CH ² - or -NR ¹ -,

R ⁴ , R ®, R ® and R ⁷ are the same as defined in [1], a salt thereof or a hydrate thereof. The following compounds are preferred among the If 'compounds.

a compound wherein ring B is B-2, a compound wherein ring B is B-3, a compound wherein ring B is B-4, a compound wherein ring B is B-5, a compound wherein ring B is B-6, a compound wherein ring B is pyridine which is substituted with lower alkyl or lower alkoxy, a compound wherein ring C is C-1, a compound wherein ring C is C-2, a compound wherein ring C is an optionally substituted morpholine ring, optionally substituted a piperazine ring, an optionally substituted imidazole ring, an optionally substituted triazole ring, or an optionally substituted pyridine ring, a compound wherein ring C is an optionally substituted morpholine ring, an optionally substituted piperazine ring, an optionally substituted imidazole ring, an optionally substituted triazole ring, or an optionally substituted pyridine ring (wherein substituent is lower alkyl, aryl or lower alkenyloxy), a compound wherein R ⁴ , R ®, R ® and R ⁷ are independently hydrogen, hydroxyl or lower alkylsulfonyloxy, a compound wherein ring B is pyridine, which is substituted with lower alkyl or lower alkoxy, ring C is an optionally substituted morpholine ring, optionally substituted. A piperazine ring, an optionally substituted imidazole ring, an optionally substituted triazole ring, or an optionally substituted pyridine ring (wherein the substituents are lower alkyl, aryl or lower alkenyloxy) and R ⁴ , R ®, R R ⁷ and R ⁷ are independently hydrogen, hydroxyl or alkylsulfonyloxy.

Another embodiment of the present invention is [5] a compound having the general formula 1g ':

wherein rings A and C are independently an optionally substituted five or six membered heterocycle containing one or two heteroatoms and W ¹ is a bond when ring A is a five membered heterocycle,

X, X ', Y and Y' are the same as defined in [1],

R 1 together with Y or Y 'form - (CH 2 -) -, - (CH 2) 2 -Q- (CH 2) 2 - (wherein Q is CH 2, O, S or NR'), -CR '= CH-CH = CR 1 -, -CH = N-CH = CH-, -N = CH-N = CH-, -C (= O) -O (CH ₂ ) n -, -C (= O) NR '- (CH 2) ) N- or -C (= O) -NR'-N = CH-, wherein m is 4 or 5, n is 2 or 3 and R 'is hydrogen, lower alkyl or lower alkenyl,

Y is optionally substituted lower alkoxy when X is -CH 2 -,

Y 'is optionally substituted lower alkoxy when X' is -CH 2 -,

Y is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl, or optionally substituted arylsulfonyl when X is -O- or -NR ¹ -,

Y 'is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl, or optionally substituted arylsulfonyl when X' is -O- or -NR ¹ -,

Y is hydrogen or halogen when X is -CH ² - or -NR ¹ -,

Y 'is hydrogen or halogen when X' is -CH ² - or -NR ¹ -,

R,, R ⁹ , R ¹⁹ and R ¹¹ are the same as defined in [1], except the compound wherein all R,, R ⁹ , R ¹⁹ and R ¹¹ are hydrogen or halogen, a salt thereof or a hydrate thereof. The following compounds are preferred among compounds 1g '.

9999

99

9999 · 9 · 9 9 9

999 99 9 · 9 a compound wherein at least one of rings A and C is a six membered ring, a compound wherein at least one of rings A and C is a six membered ring containing one nitrogen atom, a compound wherein ring A is an optionally substituted pyridine ring, a compound wherein ring A is an unsubstituted pyridine ring, a compound wherein R ®, R ⁹ , R 6 and R ⁶ are independently hydrogen, lower alkyl or lower alkoxy, a compound wherein ring C is an optionally substituted pyridine ring, an optionally substituted pyrimidine ring or an optionally substituted pyrazine ring, a compound wherein ring C is an unsubstituted pyridine ring, an unsubstituted pyrimidine ring, or an unsubstituted pyrazine ring, a compound wherein -XY is lower alkenyloxy or lower alkenylamine, a compound wherein -XY 'is an amine that is substituted with lower alkenyl a compound wherein ring a is an unsubstituted pyridine ring, R®, R ^9, R ¹ ® and R ¹¹ are each independently hydrogen, lower alkyl or lower alkoxy, ring C is an unsubstituted pyridine ring, an unsubstituted pyrimidine ring, or an unsubstituted pyrazine ring, -XY is lower alkenyloxy or lower alkenylamine and wherein -X'-Y 'is an amine substituted with lower alkenyl, or a salt thereof, or hydrate.

Other suitable embodiments of the present invention are as follows.

[6] A pharmaceutical composition for use as an immunosuppressor comprising a compound

where ring C and W® are the same as defined in [1],

X and X 'are independently -O-, -CH ² -, -NR ¹ -, (wherein R ¹ is hydrogen, optionally substituted lower alkyl, lower alkenyl, lower alkylcarbonyl, or optionally substituted lower alkoxycarbonyl), -S (O) p- (where p is an integer between 0 and 2) or a bond,

Y and Y 'are the same as defined in [1], · 9 99 ··· 9 · ··

99 ··· · · · ····

999 99 9,999

999 99 99 · · · · ·

9,999 9 · · ·

99999 9 · · 9 99

R 1 together with Y or Y 'form - (CH ₂ ) m -, - (CH ₂ ) ₂ -Q- (CH ₂ ) ₂ - (where Q is CH ₂ , O, S or NR'), -CR '= CH-CH = CR'-, -CH = N-CH = CH-, -N = CH-N = CH-, -C (= O) -O (CH ₂ ) n -, -C (= O) NR - _(CH2) n- or -C (= O) -NR'-N = CH- wherein m is 4 or 5, n is 2 or 3 and R 'is hydrogen, lower alkyl or lower alkenyl,

Y is lower alkoxy when X is -CH ₂ -,

Y 'is lower alkoxy when X' is -CH ₂ -,

Y is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl or optionally substituted lower arylsulfonyl when X is -O- or -NR ¹ -, Y 'is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl, or optionally substituted lower arylsulfonyl when X' is -O- or -NR ¹ -,

Y is hydrogen or halogen when X is -CH ₂ - or -NR ¹ -,

Y 'is hydrogen or halogen when X' is -CH ₂ - or -NR ¹ -,

Y 'is hydrogen, hydroxyl, halogen, nitro or oxo when X' is a bond,

R ⁴ , R ⁸ , R ⁸ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ are the same substituents as defined in [1], except the compound wherein all R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ is hydrogen and halogen, a salt thereof or a hydrate thereof. [7] A pharmaceutical composition for use as an immunosuppressor comprising a compound of the general formula Ia ':

wherein ring B is an optionally substituted 5- or 6-membered heterocycle containing one or two heteroatoms, with the exception of a compound wherein each substituent of ring B is cyano or halogen,

W ² is a bond when ring B is a five-membered heterocycle,

X, X ', Y and Y' are the same as defined in [3],

R 1 together with Y or Y 'form - (CH ₂ ) m -, - (CH ₂ ) ₂ -Q- (CH ₂ ) ₂ - (where Q is CH ₂ , O, S or NR'), -CR '= CH-CH = CR'-, -CH = N-CH = CH-, -N = CH-N = CH-, -C (= O) -O (CH ₂ ) n -, -C (= O) 76 • 0 0 0 0 · · ·

0 0 0 0 0 0 0 0 0 0

4 4 4 4 4 4 4 4 4 00 00 00 0 0 0 000 000

00000 00 00 00 00

NR '- (CH 2) N- or -C (= O) -NR'-N = CH-, wherein m is 4 or 5, n is 2 or 3 and R' is hydrogen, lower alkyl or lower alkenyl,

Y is optionally substituted lower alkoxy when X is -CH 2 -,

Y 'is optionally substituted lower alkoxy when X' is -CH 2 -,

Y is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl, or optionally substituted arylsulfonyl when X is -O- or -NR ¹ -,

Y 'is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl, or optionally substituted lower arylsulfonyl when X' is -O- or -NR ¹ -,

Y is hydrogen or halogen when X is -CH ² - or -NR ¹ -,

Y 'is hydrogen or halogen when X' is -CH ² - or -NR ¹ -,

R ⁴ , R ®, R ®, R ⁷ , R ¹² , R ¹ ®, R ¹⁴ and R ¹ ® are the same as defined in [3], except for (i) the compound where -XY and -X ' -Y 'are simultaneously unsubstituted lower alkyl, optionally substituted lower alkoxy or unsubstituted acyloxy, (ii) compounds wherein one of -XY and -X'-Y' is methyl and the other is methoxy, and (iii) compounds wherein -XY 'is hydrogen or halogen and -XY is unsubstituted lower alkyl, unsubstituted lower alkoxy or lower dialkylamine, a salt or a hydrate thereof, [8] a pharmaceutical composition useful as an immunosuppressor comprising a compound of the formula If', a salt or a hydrate thereof described in [4] a pharmaceutical composition useful as an immunosuppressant comprising a compound of the formula Ig ', a salt thereof or a hydrate thereof described in [5], [10] a pharmaceutical composition useful as an antiallergic agent comprising a compound of the formula If', described in [4], a compound of the general formula Ig ', described in [5], the compound of formula 1b', described in [6], the compound of formula Ia ', described in [7], a salt thereof or a hydrate thereof, [11] a pharmaceutical composition useful for inhibiting IgE production, comprising a compound of the formula If ', described in [4], a compound of the formula Ig', described in [5], a compound of the formula 1b ', described in [6], a compound of the formula Ia' described in [7], salt or hydrate, φ · · · použití použití použití použití použití použití použití použití použití použití použití použití použití použití použití [[[[[ compounds of general formula If ', described in [4], compounds of general formula Ig', described in [5], compounds of general formula 1b ', described in [6], compounds of general formula 1a', described in [7], salts thereof or a hydrate, for the manufacture of a medicament for suppressing the immune response, treating or preventing allergic diseases, [13] a method of suppressing im unity response or treatment or prevention of allergic diseases, comprising administering a compound of formula If 'described in [4], a compound of formula Ig' described in [5], a compound of formula 1b 'described in [6], a compound of formula of formula Ia 'described in [7], a salt or a hydrate thereof, and [14] a method of treating or preventing allergic diseases comprising administering a compound of the formula If' described in [4], a compound of the formula Ig 'described in [ 5], the compounds of formula 1b 'described in [6], the compounds of formula 1a' described in [7], a salt thereof or a hydrate thereof.

Preferred compounds of the present invention are the following structures. The symbols A2, A5, ... B1, B4, ... T1, T2 ... in the tables indicate the following.

ftft ··· ftft ftft • »» •

• ·· ft ftft ft · ftft · ftftft · · · · ftft ft ftft ftft

Table 1

R ⁴ R5 R ⁶ R ⁷ X Y A2 H H H H 0 CH ₂ -2-furyl A5 H H H H 0 CH ₂ CH = CMe ₂ A35 About me H H H 0 CH ₂ CH = CMe ₂ A37 F H H H 0 CH ₂ CH = CMe ₂ A45 H H H H NH ch ₂ ch = _{CH 2} A46 H H H H NH CH ₂ CH = CMe ₂ A49 H H H H NH _CH2-c-Hex A54 H H H H NH CH ₂ -2-furyl A66 H F H H NH iBu A67 H F H H NH CH ₂ CH = CMe ₂ A68 H F H H NH cPent A69 H F H H NH cHex A70 H F H H NH CH ₂ cHex A76 H F H H N-iPr SO ₂ NHMe A77 H F H H NCH ₂ CH = CMe ₂ SO ₂ NHMe A78 F H H H NH CH ₂ CH = CMe ₂ A106 H F H H NH ch ₂ c ₆ h ₅ A110 F H H H 0 ch ₂ c ₆ h ₅

• fcfc fcfc • fcfcfc fcfc fcfc • · • · 9 fc · fc fc »» • « • fcfcfc · fc • Λ • · • • • • ·· t • · • fc fcfc «· fc • • fcfc • • fc •

Table 2

R ¹¹ R ¹⁰

R ⁸ R ⁹ R ¹⁰ R ¹¹ Bl About me H H About me B4 Me H H Me B7 Me Me Me Me B8 Me Me About me Me B9 Me Me OH Me BIO Me Me Me About me B12 About me Me Me About me B14 Me Me H Me B16 Me F H Me B17 About me H H Me B24 Me Me Me COOMe B28 Me Me Me Cl B29 Me About me H Me B3O COOMe Me Me Me B31 Cl Me Me Me B32 H Me Me Cl B33 Me H Cl Me B34 H Me Cl H B35 Me H H Cl B36 Me Me H H B37 H Me H Me B38 Me H Me H B39 About me About me H H B40 H About me H About me B41 About me H About me H B42 H Me H About me B43 About me H Me H

Table 3

w ³ - ⁷ R ¹² R13 R ¹⁴ R ¹⁵ 77 W ^3-7 R ¹² R ¹³ R ¹⁴ R ¹⁵ Tl-1 H H - H T2-4 H H Me - T2-1 H H H - T2-5 H no ₂ H - T2-2 Me H H T5-1 H - H - T2-3 H Me H T7-1 H H - -

Table 4

77 w ³ - ⁷ —— W ² - ⁷ - <aV- 77 VI. ³ - ⁷ - <b) - W ^2-7 - <A / - w ^1-7 Tl-1 BI A2 T2-1 BI A2 Tl-1 BI A5 T2-1 BI A5 Tl-1 BI A35 T2-1 BI A35 Tl-1 BI A37 T2-1 BI A37 Tl-1 BI A45 T2-1 BI A45 Tl-1 BI A46 T2-1 BI A46 Tl-1 BI A49 T2-1 BI A49 Tl-1 BI A54 T2-1 BI A54 Tl-1 BI A66 T2-1 BI A66 Tl-1 BI A67 T2-1 BI A67 Tl-1 BI A68 T2-1 BI A68 Tl-1 BI A69 T2-1 BI A69 Tl-1 BI A70 T2-1 BI A70 Tl-1 BI A76 T2-1 BI A76 Tl-1 BI A77 T2-1 BI A77 Tl-1 BI A78 T2-1 BI A78 Tl-1 BI A106 T2-1 BI A106 Tl-1 BI A110 T2-1 BI A110 T2-2 BI A2 T2-3 BI A2 T2-2 BI A5 T2-3 BI A5 T2-2 BI A35 T2-3 BI A35 T2-2 BI A37 T2-3 BI A37 T2-2 BI A45 T2-3 BI A45 T2-2 BI A46 T2-3 BI A46 T2-2 BI A49 T2-3 BI A49 T2-2 BI A54 T2-3 BI A54 T2-2 BI A66 T2-3 BI A66 T2-2 BI A67 T2-3 BI A67

Table 5

T2-2 Bl A68 T2-3 Bl A68 T2-2 Bl A69 T2-3 Bl A69 T2-2 Bl A70 T2-3 Bl A70 T2-2 Bl A76 T2-3 Bl A76 T2-2 Bl A77 T2-3 Bl A77 T2-2 Bl A78 T2-3 Bl A78 T2-2 Bl A106 T2-3 Bl A106 T2-2 Bl A110 T2-3 Bl A11O T2-4 Bl A2 T2-5 Bl A2 T2-4 Bl A5 T2-5 Bl A5 T2-4 Bl A35 T2-5 Bl A35 T2-4 Bl A37 T2-5 Bl A37 T2-4 Bl A45 T2-5 Bl A45 T2-4 Bl A46 T2-5 Bl A46 T2-4 Bl A49 T2-5 Bl A49 T2-4 Bl A54 T2-5 Bl A54 T2-4 Bl A66 T2-5 Bl A66 T2-4 Bl A67 T2-5 Bl A67 T2-4 Bl A68 T2-5 Bl A68 T2-4 Bl A69 T2-5 Bl A69 T2-4 Bl A70 T2-5 Bl A7O T2-4 Bl A76 T2-5 Bl A76 T2-4 Bl A77 T2-5 Bl A77 T2-4 Bl A78 T2-5 Bl A78 T2-4 Bl A106 T2-5 Bl A106 T2-4 Bl A11O T2-5 Bl A11O T5-1 Bl A2 T7-1 Bl A2 T5-1 Bl A5 T7-1 Bl A5 T5-1 Bl A35 T7-1 Bl A35 T5-1 Bl A37 T7-1 Bl A37 T5-1 Bl A45 T7-1 Bl A45 T5-1 Bl A46 T7-1 Bl A46 T5-1 Bl A49 T7-1 Bl A49 T5-1 Bl A54 T7-1 Bl A54 T5-1 Bl A66 T7-1 Bl A66 T5-1 Bl A67 T7-1 Bl A67 T5-1 Bl A68 T7-1 Bl A68 T5-1 Bl A69 T7-1 Bl A69 T5-1 Bl A7O T7-1 Bl A70 T5-1 Bl A76 T7-1 Bl A76 T5-1 Bl A77 T7-1 Bl A77 T5-1 Bl A78 T7-1 Bl A78 T5-1 Bl A106 T7-1 Bl A106 T5-1 Bl A11O T7-1 Bl A11O

• · ··················

Table 6

Tl-1 B4 A2 T2-1 B4 A2 Tl-1 B4 A5 T2-1 B4 A5 Tl-1 B4 A35 T2-1 B4 A35 Tl-1 B4 A37 T2-1 B4 A37 Tl-1 B4 A45 T2-1 B4 A45 Tl-1 B4 A46 T2-1 B4 A46 Tl-1 B4 A49 T2-1 B4 A49 Tl-1 B4 A54 T2-1 B4 A54 Tl-1 B4 A66 T2-1 B4 A66 Tl-1 B4 A67 T2-1 B4 A67 Tl-1 B4 A68 T2-1 B4 A68 Tl-1 B4 A69 T2-1 B4 A69 Tl-1 B4 A70 T2-1 B4 A70 Tl-1 B4 A76 T2-1 B4 A76 Tl-1 B4 A77 T2-1 B4 A77 Tl-1 B4 A78 T2-1 B4 A78 Tl-1 B4 A106 T2-1 B4 A106 Tl-1 B4 A110 T2-1 B4 A11O T2-2 B4 A2 T2-3 B4 A2 T2-2 B4 A5 T2-3 B4 A5 T2-2 B4 A35 T2-3 B4 A35 T2-2 B4 A37 T2-3 B4 A37 T2-2 B4 A45 T2-3 B4 A45 T2-2 B4 A46 T2-3 B4 A46 T2-2 B4 A49 T2-3 B4 A49 T2-2 B4 A54 T2-3 B4 A54 T2-2 B4 A66 T2-3 B4 A66 T2-2 B4 A67 T2-3 B4 A67 T2-2 B4 A68 T2-3 B4 A68 T2-2 B4 A69 T2-3 B4 A69 T2-2 B4 A70 T2-3 B4 A70 T2-2 B4 A76 T2-3 B4 A76 T2-2 B4 A77 T2-3 B4 A77 T2-2 B4 A78 T2-3 B4 A78 T2-2 B4 A106 T2-3 B4 A106 T2-2 B4 A11O T2-3 B4 A11O T2-4 B4 A2 T2-5 B4 A2 T2-4 B4 A5 T2-5 B4 A5 T2-4 B4 A35 T2-5 B4 A35 T2-4 B4 A37 T2-5 B4 A37 T2-4 B4 A45 T2-5 B4 A45 T2-4 B4 A46 T2-5 B4 A46 T2-4 B4 A49 T2-5 B4 A49 T2-4 B4 A54 T2-5 B4 A54

Table 7 ·····

T2-4 B4 A66 T2-5 B4 A66 T2-4 B4 A67 T2-5 B4 A67 T2-4 B4 A68 T2-5 B4 A68 T2-4 B4 A69 T2-5 B4 A69 T2-4 B4 A70 T2-5 B4 A70 T2-4 B4 A76 T2-5 B4 A76 T2-4 B4 A77 T2-5 B4 A77 T2-4 B4 A78 T2-5 B4 A78 T2-4 B4 A106 T2-5 B4 A106 T2-4 B4 A110 T2-5 B4 A11O T5-1 B4 A2 T7-1 B4 A2 T5-1 B4 A5 T7-1 B4 A5 T5-1 B4 A35 T7-1 B4 A35 T5-1 B4 A37 T7-1 B4 A37 T5-1 B4 A45 T7-1 B4 A45 T5-1 B4 A46 T7-1 B4 A46 T5-1 B4 A49 T7-1 B4 A49 T5-1 B4 A54 T7-1 B4 A54 T5-1 B4 A66 T7-1 B4 A66 T5-1 B4 A67 T7-1 B4 A67 T5-1 B4 A68 T7-1 B4 A68 T5-1 B4 A69 T7-1 B4 A69 T5-1 B4 A7O T7-1 B4 A70 T5-1 B4 A76 T7-1 B4 A76 T5-1 B4 A77 T7-1 B4 A77 T5-1 B4 A78 T7-1 B4 A78 T5-1 B4 A106 T7-1 B4 A106 T5-1 B4 A11O T7-1 B4 A11O Tl-1 B7 A2 T2-1 B7 A2 Tl-1 B7 A5 T2-1 B7 A5 Tl-1 B7 A35 T2-1 B7 A35 Tl-1 B7 A37 T2-1 B7 A37 Tl-1 B7 A45 T2-1 B7 A45 Tl-1 B7 A46 T2-1 B7 A46 Tl-1 B7 A49 T2-1 B7 A49 Tl-1 B7 A54 T2-1 B7 A54 Tl-1 B7 A66 T2-1 B7 A66 Tl-1 B7 A67 T2-1 B7 A67 Tl-1 B7 A68 T2-1 B7 A68 Tl-1 B7 A69 T2-1 B7 A69 Tl-1 B7 A7O T2-1 B7 A70 Tl-1 B7 A76 T2-1 B7 A76 Tl-1 B7 A77 T2-1 B7 A77 Tl-1 B7 A78 T2-1 B7 A78

Table 8 · φ φ φ φ φ φ φ φ φ φ φ

ΦΦΦ Φ Φ Φ φ φ · Φ Φ Φ Φ

-11-1 Β7 Α106 -12-1 Β7 Α106 -11-1 Β7 Α110 -12-1 Β7 Α110 -22-2 Β7 Α2 -2-3 Β7 Α2 -22-2 Β7 Α5 -2-3 Β7 Α5 -22-2 Β7 Α35 -2-3 Β7 Α35 -22-2 Β7 Α37 -2-3 Β7 Α37 -22-2 Β7 Α45 -2-3 Β7 Α45 -22-2 Β7 Α46 -2-3 Β7 Α46 -22-2 Β7 Α49 -2-3 Β7 Α49 -22-2 Β7 Α54 -2-3 Β7 Α54 -22-2 Β7 Α66 -2-3 Β7 Α66 -22-2 Β7 Α67 -2-3 Β7 Α67 -22-2 Β7 Α68 -2-3 Β7 Α68 -22-2 Β7 Α69 -2-3 Β7 Α69 -22-2 Β7 Α70 -2-3 Β7 Α70 -22-2 Β7 Α76 -2-3 Β7 Α76 -22-2 Β7 Α77 -2-3 Β7 Α77 -22-2 Β7 Α78 -2-3 Β7 Α78 -22-2 Β7 Α106 -2-3 Β7 Α106 -22-2 Β7 Α110 -2-3 Β7 Α110 -42-4 Β7 Α2 -52-5 Β7 Α2 -42-4 Β7 Α5 -52-5 Β7 Α5 -42-4 Β7 Α35 -52-5 Β7 Α35 -42-4 Β7 Α37 -52-5 Β7 Α37 -42-4 Β7 Α45 -52-5 Β7 Α45 -42-4 Β7 Α46 -52-5 Β7 Α46 -42-4 Β7 Α49 -52-5 Β7 Α49 -42-4 Β7 Α54 -52-5 Β7 Α54 -42-4 Β7 Α66 -52-5 Β7 Α66 -42-4 Β7 Α67 -52-5 Β7 Α67 -42-4 Β7 Α68 -52-5 Β7 Α68 -42-4 Β7 Α69 -52-5 Β7 Α69 -42-4 Β7 Α70 -52-5 Β7 Α70 -42-4 Β7 Α76 -52-5 Β7 Α76 -42-4 Β7 Α77 -52-5 Β7 Α77 Τ2-4 Β7 Α78 -52-5 Β7 Α78 -42-4 Β7 Α106 -52-5 Β7 Α106 Τ2-4 Β7 Α110 -52-5 Β7 Α110 -15-1 Β7 Α2 -17-1 Β7 Α2 -15-1 Β7 Α5 -17-1 Β7 Α5 -15-1 Β7 Α35 -17-1 Β7 Α35 -15-1 Β7 Α37 -17-1 Β7 Α37 -15-1 Β7 Α45 -17-1 Β7 Α45

Table 9 φ φ φ φ φ φ · · φ φ φ φ φ φ φ φ

-15-1 Β7 Α46 -17-1 Β7 Α46 Τ5Π Β7 Α49 -17-1 Β7 Α49 -15-1 Β7 Α54 -17-1 Β7 Α54 -15-1 Β7 Α66 -17-1 Β7 Α66 -15-1 Β7 Α67 -17-1 Β7 Α67 -15-1 Β7 Α68 -17-1 Β7 Α68 -15-1 Β7 Α69 -17-1 Β7 Α69 -15-1 Β7 Α70 -17-1 Β7 Α70 -15-1 Β7 Α76 -17-1 Β7 Α76 -15-1 Β7 Α77 -17-1 Β7 Α77 -15-1 Β7 Α78 -17-1 Β7 Α78 -15-1 Β7 Α106 -17-1 Β7 Α106 -15-1 Β7 Α110 -17-1 Β7 Α110 -11-1 Β8 Α2 -12-1 Β8 Α2 -11-1 Β8 Α5 -12-1 Β8 Α5 -11-1 Β8 Α35 -12-1 Β8 Α35 -11-1 Β8 Α37 -12-1 Β8 Α37 -11-1 Β8 Α45 -12-1 Β8 Α45 -11-1 Β8 Α46 -12-1 Β8 Α46 -11-1 Β8 Α49 -12-1 Β8 Α49 -11-1 Β8 Α54 -12-1 Β8 Α54 -11-1 Β8 Α66 -12-1 Β8 Α66 -11-1 Β8 Α67 -12-1 Β8 Α67 -11-1 Β8 Α68 -12-1 Β8 Α68 -11-1 Β8 Α69 -12-1 Β8 Α69 -11-1 Β8 Α70 -12-1 Β8 Α70 -11-1 Β8 Α76 -12-1 Β8 Α76 -11-1 Β8 Α77 -12-1 Β8 Α77 -11-1 Β8 Α78 -12-1 Β8 Α78 -11-1 Β8 Α106 -12-1 Β8 Α106 -11-1 Β8 Α110 -12-1 Β8 Α110 -22-2 Β8 Α2 -2-3 Β8 Α2 -22-2 Β8 Α5 -2-3 Β8 Α5 -22-2 Β8 Α35 -2-3 Β8 Α35 -22-2 Β8 Α37 -2-3 Β8 Α37 -22-2 Β8 Α45 -2-3 Β8 Α45 -22-2 Β8 Α46 -2-3 Β8 Α46 -22-2 Β8 Α49 -2-3 Β8 Α49 -22-2 Β8 Α54 -2-3 Β8 Α54 -22-2 Β8 Α66 -2-3 Β8 Α66 -22-2 Β8 Α67 -2-3 Β8 Α67 -22-2 Β8 Α68 -2-3 Β8 Α68 -22-2 Β8 Α69 -2-3 Β8 Α69

····· · · · · · · · · · · · · · · · · · · ·

Table 10

T2-2 B8 A70 T2-3 B8 A70 T2-2 B8 A76 T2-3 B8 A76 T2-2 B8 A77 T2-3 B8 A77 T2-2 B8 A78 T2-3 B8 A78 T2-2 B8 A106 T2-3 B8 A106 T2-2 B8 A110 T2-3 B8 A110 T2-4 B8 A2 T2-5 B8 A2 T2-4 B8 A5 T2-5 B8 A5 T2-4 B8 A35 T2-5 B8 A35 T2-4 B8 A37 T2-5 B8 A37 T2-4 B8 A45 T2-5 B8 A45 T2-4 B8 A46 T2-5 B8 A46 T2-4 B8 A49 T2-5 B8 A49 T2-4 B8 A54 T2-5 B8 A54 T2-4 B8 A66 T2-5 B8 A66 T2-4 B8 A67 T2-5 B8 A67 T2-4 B8 A68 T2-5 B8 A68 T2-4 B8 A69 T2-5 B8 A69 T2-4 B8 A70 T2-5 B8 A70 T2-4 B8 A76 T2-5 B8 A76 T2-4 B8 A77 T2-5 B8 A77 T2-4 B8 A78 T2-5 B8 A78 T2-4 B8 A106 T2-5 B8 A106 T2-4 B8 A110 T2-5 B8 A110 T5-1 B8 A2 T7-1 B8 A2 T5-1 B8 A5 T7-1 B8 A5 T5-1 B8 A35 T7-1 B8 A35 T5-1 B8 A37 T7-1 B8 A37 T5-1 B8 A45 T7-1 B8 A45 T5-1 B8 A46 T7-1 B8 A46 T5-1 B8 A49 T7-1 B8 A49 T5-1 B8 A54 T7-1 B8 A54 T5-1 B8 A66 T7-1 B8 A66 T5-1 B8 A67 T7-1 B8 A67 T5-1 B8 A68 T7-1 B8 A68 T5-1 B8 A69 T7-1 B8 A69 T5-1 B8 A70 T7-1 B8 A70 T5-1 B8 A76 T7-1 B8 A76 T5-1 B8 A77 T7-1 B8 A77 T5-1 B8 A78 T7-1 B8 A78 T5-1 B8 A106 T7-1 B8 A106 T5-1 B8 A110 T7-1 B8 A110 Tl-1 B9 A2 T2-1 B9 A2

Table 11

··· ·· · 9 · 9 9

Tl-1 B9 A5 | T2-1 B9 A5 Tl-1 B9 A35 T2-1 B9 A35 Tl-1 B9 A37 T2-1 B9 A37 Tl-1 B9 A45 T2-1 B9 A45 Tl-1 B9 A46 T2-1 B9 A46 Tl-1 B9 A49 T2-1 B9 A49 Tl-1 B9 A54 T2-1 B9 A54 Tl-1 B9 A66 T2-1 B9 A66 Tl-1 B9 A67 T2-1 B9 A67 Tl-1 B9 A68 T2-1 B9 A68 Tl-1 B9 A69 T2-1 B9 A69 Tl-1 B9 A70 T2-1 B9 A70 Tl-1 B9 A76 T2-1 B9 A76 Tl-1 B9 A77 T2-1 B9 A77 Tl-1 B9 A78 T2-1 B9 A78 Tl-1 B9 A106 T2-1 B9 A106 Tl-1 B9 A110 T2-1 B9 A110 T2-2 B9 A2 T2-3 B9 A2 T2-2 B9 A5 T2-3 B9 A5 T2-2 B9 A35 T2-3 B9 A35 T2-2 B9 A37 T2-3 B9 A37 T2-2 B9 A45 T2-3 B9 A45 T2-2 B9 A46 T2-3 B9 A46 T2-2 B9 A49 T2-3 B9 A49 T2-2 B9 A54 T2-3 B9 A54 T2-2 B9 A66 T2-3 B9 A66 T2-2 B9 A67 T2-3 B9 A67 T2-2 B9 A68 T2-3 B9 A68 T2-2 B9 A69 T2-3 B9 A69 T2-2 B9 A70 T2-3 B9 A70 T2-2 B9 A76 T2-3 B9 A76 T2-2 B9 A77 T2-3 B9 A77 T2-2 B9 A78 T2-3 B9 A78 T2-2 B9 A106 T2-3 B9 A106 T2-2 B9 A11O T2-3 B9 A110 T2-4 B9 A2 T2-5 B9 A2 T2-4 B9 A5 T2-5 B9 A5 T2-4 B9 A35 T2-5 B9 A35 T2-4 B9 A37 T2-5 B9 A37 T2-4 B9 A45 T2-5 B9 A45 T2-4 B9 A46 T2-5 B9 A46 T2-4 B9 A49 T2-5 B9 A49 T2-4 B9 A54 T2-5 B9 A54

Table 12

T2-4 B9 A66 T2-5 B9 A66 T2-4 B9 A67 T2-5 B9 A67 T2-4 B9 A68 T2-5 B9 A68 T2-4 B9 A69 T2-5 B9 A69 T2-4 B9 A70 T2-5 B9 A70 T2-4 B9 A76 T2-5 B9 A76 T2-4 B9 A77 T2-5 B9 A77 T2-4 B9 A78 T2-5 B9 A78 T2-4 B9 A106 T2-5 B9 A106 T2-4 B9 A11O T2-5 B9 A11O T5-1 B9 A2 T7-1 B9 A2 T5-1 B9 A5 T7-1 B9 A5 T5-1 B9 A35 T7-1 B9 A35 T5-1 B9 A37 T7-1 B9 A37 T5-1 B9 A45 T7-1 B9 A45 T5-1 B9 A46 T7-1 B9 A46 T5-1 B9 A49 T7-1 B9 A49 T5-1 B9 A54 T7-1 B9 A54 T5-1 B9 A66 T7-1 B9 A66 T5-1 B9 A67 T7-1 B9 A67 T5-1 B9 A68 T7-1 B9 A68 T5-1 B9 A69 T7-1 B9 A69 T5-1 B9 A70 T7-1 B9 A70 T5-1 B9 A76 T7-1 B9 A76 T5-1 B9 A77 T7-1 B9 A77 T5-1 B9 A78 T7-1 B9 A78 T5-1 B9 A106 T7-1 B9 A106 T5-1 B9 A11O T7-1 B9 A11O Tl-1 BIO A2 T2-1 BIO A2 Tl-1 BIO A5 T2-1 BIO A5 Tl-1 BIO A35 T2-1 BIO A35 Tl-1 BIO A37 T2-1 BIO A37 Tl-1 BIO A45 T2-1 BIO A45 Tl-1 BIO A46 T2-1 BIO A46 Tl-1 BIO A49 T2-1 BIO A49 Tl-1 BIO A54 T2-1 BIO A54 Tl-1 BIO A66 T2-1 BIO A66 Tl-1 BIO A67 T2-1 BIO A67 Tl-1 BIO A68 T2-1 BIO A68 Tl-1 BIO A69 T2-1 BIO A69 Tl-1 BIO A70 T2-1 BIO A70 Tl-1 BIO A76 T2-1 BIO A76 Tl-1 BIO A77 T2-1 BIO A77 Tl-1 BIO A78 T2-1 BIO A78

Table 13

ΦΦ · · · · · · · · · · · · · · · · · · · · · · ·

-11-1 ΒΙΟ Α106 -12-1 ΒΙΟ Α106 -11-1 ΒΙΟ Α11Ο -12-1 ΒΙΟ Α11Ο -22-2 ΒΙΟ Α2 -2-3 ΒΙΟ Α2 -22-2 ΒΙΟ Α5 -2-3 ΒΙΟ Α5 -22-2 ΒΙΟ Α35 -2-3 ΒΙΟ Α35 -22-2 ΒΙΟ Α37 -2-3 ΒΙΟ Α37 -22-2 ΒΙΟ Α45 -2-3 ΒΙΟ Α45 -22-2 ΒΙΟ Α46 -2-3 ΒΙΟ Α46 -22-2 ΒΙΟ Α49 -2-3 ΒΙΟ Α49 -22-2 ΒΙΟ Α54 -2-3 ΒΙΟ Α54 -22-2 ΒΙΟ Α66 -2-3 ΒΙΟ Α66 -22-2 ΒΙΟ Α67 -2-3 ΒΙΟ Α67 -22-2 ΒΙΟ Α68 -2-3 ΒΙΟ Α68 -22-2 ΒΙΟ Α69 -2-3 ΒΙΟ Α69 -22-2 ΒΙΟ Α7Ο -2-3 ΒΙΟ Α70 -22-2 ΒΙΟ Α76 -2-3 ΒΙΟ Α76 -22-2 ΒΙΟ Α77 -2-3 ΒΙΟ Α77 -22-2 ΒΙΟ Α78 -2-3 ΒΙΟ Α78 -22-2 ΒΙΟ Α106 -2-3 ΒΙΟ Α106 -22-2 ΒΙΟ Α11Ο -2-3 ΒΙΟ Α11Ο Τ2-4 ΒΙΟ Α2 -52-5 ΒΙΟ Α2 Τ2-4 ΒΙΟ Α5 -52-5 ΒΙΟ Α5 Τ2-4 ΒΙΟ Α35 -52-5 ΒΙΟ Α35 Τ2-4 ΒΙΟ Α37 -52-5 ΒΙΟ Α37 Τ2-4 ΒΙΟ Α45 -52-5 ΒΙΟ Α45 Τ2-4 ΒΙΟ Α46 -52-5 ΒΙΟ Α46 Τ2-4 ΒΙΟ Α49 -52-5 ΒΙΟ Α49 Τ2-4 ΒΙΟ Α54 -52-5 ΒΙΟ Α54 Τ2-4 ΒΙΟ Α66 -52-5 ΒΙΟ Α66 Τ2-4 ΒΙΟ Α67 -52-5 ΒΙΟ Α67 Τ2-4 ΒΙΟ Α68 -52-5 ΒΙΟ Α68 Τ2-4 ΒΙΟ Α69 -52-5 ΒΙΟ Α69 Τ2-4 ΒΙΟ Α7Ο -52-5 ΒΙΟ Α70 Τ2-4 ΒΙΟ Α76 -52-5 ΒΙΟ Α76 Τ2-4 ΒΙΟ Α77 -52-5 ΒΙΟ Α77 Τ2-4 ΒΙΟ Α78 -52-5 ΒΙΟ Α78 Τ2-4 ΒΙΟ Α106 -52-5 ΒΙΟ Α106 Τ2-4 ΒΙΟ Α11Ο -52-5 ΒΙΟ Α11Ο -15-1 ΒΙΟ Α2 -17-1 ΒΙΟ Α2 -15-1 ΒΙΟ Α5 -17-1 ΒΙΟ Α5 -15-1 ΒΙΟ Α35 -17-1 ΒΙΟ Α35 -15-1 ΒΙΟ Α37 -17-1 ΒΙΟ Α37 -15-1 ΒΙΟ Α45 -17-1 ΒΙΟ Α45

Table 14 • tt

T5-1 BIO A46 T7-1 BIO A46 T5-1 BIO A49 T7-1 BIO A49 T5-1 BIO A54 T7-1 BIO A54 T5-1 BIO A66 T7-1 BIO A66 T5-1 BIO A67 T7-1 BIO A67 T5-1 BIO A68 T7-1 BIO A68 T5-1 BIO A69 T7-1 BIO A69 T5-1 BIO A70 T7-1 BIO A70 T5-1 BIO A76 T7-1 BIO A76 T5-1 BIO A77 T7-1 BIO A77 T5-1 BIO A78 T7-1 BIO A78 T5-1 BIO A106 T7-1 BIO A106 T5-1 BIO A110 T7-1 BIO A110 Tl-1 B12 A2 T2-1 B12 A2 Tl-1 B12 A5 T2-1 B12 A5 Tl-1 B12 A35 T2-1 B12 A35 Tl-1 B12 A37 T2-1 B12 A37 Tl-1 B12 A45 T2-1 B12 A45 Tl-1 B12 A46 T2-1 B12 A46 Tl-1 B12 A49 T2-1 B12 A49 Tl-1 B12 A54 T2-1 B12 A54 Tl-1 B12 A66 T2-1 B12 A66 Tl-1 B12 A67 T2-1 B12 A67 Tl-1 B12 A68 T2-1 B12 A68 Tl-1 B12 A69 T2-1 B12 A69 Tl-1 B12 A70 T2-1 B12 A70 Tl-1 B12 A76 T2-1 B12 A76 Tl-1 B12 A77 T2-1 B12 A77 Tl-1 B12 A78 T2-1 B12 A78 Tl-1 B12 A106 T2-1 B12 A106 Tl-1 B12 A110 T2-1 B12 A110 T2-2 B12 A2 T2-3 B12 A2 T2-2 B12 A5 T2-3 B12 A5 T2-2 B12 A35 T2-3 B12 A35 T2-2 B12 A37 T2-3 B12 A37 T2-2 B12 A45 T2-3 B12 A45 T2-2 B12 A46 T2-3 B12 A46 T2-2 B12 A49 T2-3 B12 A49 T2-2 B12 A54 T2-3 B12 A54 T2-2 B12 A66 T2-3 B12 A66 T2-2 B12 A67 T2-3 B12 A67 T2-2 B12 A68 T2-3 B12 A68 T2-2 B12 A69 T2-3 B12 A69

·· «··· ··

Table 15 • 9 9 9 99

T2-2 B12 A70 T2-3 B12 A70 T2-2 B12 A76 T2-3 B12 A76 T2-2 B12 A77 T2-3 B12 A77 T2-2 B12 A78 T2-3 B12 A78 T2-2 B12 A106 T2-3 B12 A106 T2-2 B12 A110 T2-3 B12 A11O T2-4 B12 A2 T2-5 B12 A2 T2-4 B12 A5 T2-5 B12 A5 T2-4 B12 A35 T2-5 B12 A35 T2-4 B12 A37 T2-5 B12 A37 T2-4 B12 A45 T2-5 B12 A45 T2-4 B12 A46 T2-5 B12 A46 T2-4 B12 A49 T2-5 B12 A49 T2-4 B12 A54 T2-5 B12 A54 T2-4 B12 A66 T2-5 B12 A66 T2-4 B12 A67 T2-5 B12 A67 T2-4 B12 A68 T2-5 B12 A68 T2-4 B12 A69 T2-5 B12 A69 T2-4 B12 A70 T2-5 B12 A70 T2-4 B12 A76 T2-5 B12 A76 T2-4 B12 A77 T2-5 B12 A77 T2-4 B12 A78 T2-5 B12 A78 T2-4 B12 A106 T2-5 B12 A106 T2-4 B12 A11O T2-5 B12 A11O T5-1 B12 A2 T7-1 B12 A2 T5-1 B12 A5 T7-1 B12 A5 T5-1 B12 A35 T7-1 B12 A35 T5-1 B12 A37 T7-1 B12 A37 T5-1 B12 A45 T7-1 B12 A45 T5-1 B12 A46 T7-1 B12 A46 T5-1 B12 A49 T7-1 B12 A49 T5-1 B12 A54 T7-1 B12 A54 T5-1 B12 A66 T7-1 B12 A66 T5-1 B12 A67 T7-1 B12 A67 T5-1 B12 A68 T7-1 B12 A68 T5-1 B12 A69 T7-1 B12 A69 T5-1 B12 A70 T7-1 B12 A7O T5-1 B12 A76 T7-1 B12 A76 T5-1 B12 A77 T7-1 B12 A77 T5-1 B12 A78 T7-1 B12 A78 T5-1 B12 A106 T7-1 B12 A106 T5-1 B12 A11O T7-1 B12 A11O Tl-1 B14 A2 T2-1 B14 A2

0 «0»

Table 16

Tl-1 B14 A5 T2-1 B14 A5 Tl-1 B14 A35 T2-1 B14 A35 Tl-1 B14 A37 T2-1 B14 A37 Tl-1 B14 A45 T2-1 B14 A45 Tl-1 B14 A46 T2-1 B14 A46 Tl-1 B14 A49 T2-1 B14 A49 Tl-1 B14 A54 T2-1 B14 A54 Tl-1 B14 A66 T2-1 B14 A66 Tl-1 B14 A67 T2-1 B14 A67 Tl-1 B14 A68 T2-1 B14 A68 Tl-1 B14 A69 T2-1 B14 A69 Tl-1 B14 A70 T2-1 B14 A7O Tl-1 B14 A76 T2-1 B14 A76 Tl-1 B14 A77 T2-1 B14 A77 Tl-1 B14 A78 T2-1 B14 A78 Tl-1 B14 A106 T2-1 B14 A106 Tl-1 B14 A110 T2-1 B14 A11O T2-2 B14 A2 T2-3 B14 A2 T2-2 B14 A5 T2-3 B14 A5 T2-2 B14 A35 T2-3 B14 A35 T2-2 B14 A37 T2-3 B14 A37 T2-2 B14 A45 T2-3 B14 A45 T2-2 B14 A46 T2-3 B14 A46 T2-2 B14 A49 T2-3 B14 A49 T2-2 B14 A54 T2-3 B14 A54 T2-2 B14 A66 T2-3 B14 A66 T2-2 B14 A67 T2-3 B14 A67 T2-2 B14 A68 T2-3 B14 A68 T2-2 B14 A69 T2-3 B14 A69 T2-2 B14 A70 T2-3 B14 A70 T2-2 B14 A76 T2-3 B14 A76 T2-2 B14 A77 T2-3 B14 A77 T2-2 B14 A78 T2-3 B14 A78 T2-2 B14 A106 T2-3 B14 A106 T2-2 B14 A11O T2-3 B14 A11O T2-4 B14 A2 T2-5 B14 A2 T2-4 B14 A5 T2-5 B14 A5 T2-4 B14 A35 T2-5 B14 A35 T2-4 B14 A37 T2-5 B14 A37 T2-4 B14 A45 T2-5 B14 A45 T2-4 B14 A46 T2-5 B14 A46 T2-4 B14 A49 T2-5 B14 A49 T2-4 B14 A54 T2-5 B14 A54

»»

Table 17 fcfcfc 9 fcfc fcfcfcfc fcfc fcfc fcfc fcfc fcfc fcfc

T2-4 B14 A66 T2-5 B14 A66 T2-4 B14 A67 T2-5 B14 A67 T2-4 B14 A68 T2-5 B14 A68 T2-4 B14 A69 T2-5 B14 A69 T2-4 B14 A70 T2-5 B14 A70 T2-4 B14 A76 T2-5 B14 A76 T2-4 B14 A77 T2-5 B14 A77 T2-4 B14 A78 T2-5 B14 A78 T2-4 B14 A106 T2-5 B14 A106 T2-4 B14 AllO T2-5 B14 AllO T5-1 B14 A2 T7-1 B14 A2 T5-1 B14 A5 T7-1 B14 A5 T5-1 B14 A35 T7-1 B14 A35 T5-1 B14 A37 T7-1 B14 A37 T5-1 B14 A45 T7-1 B14 A45 T5-1 B14 A46 T7-1 B14 A46 T5-1 B14 A49 T7-1 B14 A49 T5-1 B14 A54 T7-1 B14 A54 T5-1 B14 A66 T7-1 B14 A66 T5-1 B14 A67 T7-1 B14 A67 T5-1 B14 A68 T7-1 B14 A68 T5-1 B14 A69 T7-1 B14 A69 T5-1 B14 A70 T7-1 B14 A7O T5-1 B14 A76 T7-1 B14 A76 T5-1 B14 A77 T7-1 B14 A77 T5-1 B14 A78 T7-1 B14 A78 T5-1 B14 A106 T7-1 B14 A106 T5-1 B14 AllO T7-1 B14 AllO Tl-1 B16 A2 T2-1 B16 A2 Tl-1 B16 A5 T2-1 B16 A5 Tl-1 B16 A35 T2-1 B16 A35 Tl-1 B16 A37 T2-1 B16 A37 Tl-1 B16 A45 T2-1 B16 A45 Tl-1 B16 A46 T2-1 B16 A46 Tl-1 B16 A49 T2-1 B16 A49 Tl-1 B16 A54 T2-1 B16 A54 Tl-1 B16 A66 T2-1 B16 A66 Tl-1 B16 A67 T2-1 B16 A67 Tl-1 B16 A68 T2-1 B16 A68 Tl-1 B16 A69 T2-1 B16 A69 Tl-1 B16 A70 T2-1 B16 A7O Tl-1 B16 A76 T2-1 B16 A76 Tl-1 B16 A77 T2-1 B16 A77

Table 18 ftft ftftft ft ftftft ftftft ftft ftft ftft ftft ftft ftft ftft ftft ftft ftft ftft ftftft ftftft ftftft ftftft ftftft ftftft

Tl-1 B16 A78 T2-1 B16 A78 Tl-1 B16 A106 T2-1 B16 A106 Tl-1 B16 A110 T2-1 B16 A11O T2-2 B16 A2 T2-3 B16 A2 T2-2 B16 A5 T2-3 B16 A5 T2-2 B16 A35 T2-3 B16 A35 T2-2 B16 A37 T2-3 B16 A37 T2-2 B16 A45 T2-3 B16 A45 T2-2 B16 A46 T2-3 B16 A46 T2-2 B16 A49 T2-3 B16 A49 T2-2 B16 A54 T2-3 B16 A54 T2-2 B16 A66 T2-3 B16 A66 T2-2 B16 A67 T2-3 B16 A67 T2-2 B16 A68 T2-3 B16 A68 T2-2 B16 A69 T2-3 B16 A69 T2-2 B16 A70 T2-3 B16 A7O T2-2 B16 A76 T2-3 B16 A76 T2-2 B16 A77 T2-3 B16 A77 T2-2 B16 A78 T2-3 B16 A78 T2-2 B16 A106 T2-3 B16 A106 T2-2 B16 A11O T2-3 B16 A11O T2-4 B16 A2 T2-5 B16 A2 T2-4 B16 A5 T2-5 B16 A5 T2-4 B16 A35 T2-5 B16 A35 T2-4 B16 A37 T2-5 B16 A37 T2-4 B16 A45 T2-5 B16 A45 T2-4 B16 A46 T2-5 B16 A46 T2-4 B16 A49 T2-5 B16 A49 T2-4 B16 A54 T2-5 B16 A54 T2-4 B16 A66 T2-5 B16 A66 T2-4 B16 A67 T2-5 B16 A67 T2-4 B16 A68 T2-5 B16 A68 T2-4 B16 A69 T2-5 B16 A69 T2-4 B16 A7O T2-5 B16 A70 T2-4 B16 A76 T2-5 B16 A76 T2-4 B16 A77 T2-5 B16 A77 T2-4 B16 A78 T2-5 B16 A78 T2-4 B16 A106 T2-5 B16 A106 T2-4 B16 A11O T2-5 B16 A11O T5-1 B16 A2 T7-1 B16 A2 T5-1 B16 A5 T7-1 B16 A5 T5-1 B16 A35 T7-1 B16 A35 T5-1 B16 A37 T7-1 B16 A37

Table 19

T5-1 B16 A45 T7-1 B16 A45 T5-1 B16 A46 T7-1 B16 A46 T5-1 B16 A49 T7-1 B16 A49 T5-1 B16 A54 T7-1 B16 A54 T5-1 B16 A66 T7-1 B16 A66 T5-1 B16 A67 T7-1 B16 A67 T5-1 B16 A68 T7-1 B16 A68 T5-1 B16 A69 T7-1 B16 A69 T5-1 B16 A70 T7-1 B16 A70 T5-1 B16 A76 T7-1 B16 A76 T5-1 B16 A77 T7-1 B16 A77 T5-1 B16 A78 T7-1 B16 A78 T5-1 B16 A106 T7-1 B16 A106 T5-1 B16 A110 T7-1 B16 A11O Tl-1 B17 A2 T2-1 B17 A2 Tl-1 B17 A5 T2-1 B17 A5 Tl-1 B17 A35 T2-1 B17 A35 Tl-1 B17 A37 T2-1 B17 A37 Tl-1 B17 A45 T2-1 B17 A45 Tl-1 B17 A46 T2-1 B17 A46 Tl-1 B17 A49 T2-1 B17 A49 Tl-1 B17 A54 T2-1 B17 A54 Tl-1 B17 A66 T2-1 B17 A66 Tl-1 B17 A67 T2-1 B17 A67 Tl-1 B17 A68 T2-1 B17 A68 Tl-1 B17 A69 T2-1 B17 A69 Tl-1 B17 A70 T2-1 B17 A70 Tl-1 B17 A76 T2-1 B17 A76 Tl-1 B17 A77 T2-1 B17 A77 Tl-1 B17 A78 T2-1 B17 A78 Tl-1 B17 A106 T2-1 B17 A106 Tl-1 B17 A11O T2-1 B17 A11O T2-2 B17 A2 T2-3 B17 A2 T2-2 B17 A5 T2-3 B17 A5 T2-2 B17 A35 T2-3 B17 A35 T2-2 B17 A37 T2-3 B17 A37 T2-2 B17 A45 T2-3 B17 A45 T2-2 B17 A46 T2-3 B17 A46 T2-2 B17 A49 T2-3 B17 A49 T2-2 B17 A54 T2-3 B17 A54 T2-2 B17 A66 T2-3 B17 A66 T2-2 B17 A67 T2-3 B17 A67 T2-2 B17 A68 T2-3 B17 A68

• · 4 4 • 4 · 4 ♦

4 4 ♦

4 · · 4

4 4 4

Table 20

T2-2 B17 A69 T2-3 B17 A69 T2-2 B17 A7O T2-3 B17 A70 T2-2 B17 A76 T2-3 B17 A76 T2-2 B17 A77 T2-3 B17 A77 T2-2 B17 A78 T2-3 B17 A78 T2-2 B17 A106 T2-3 B17 A106 T2-2 B17 A110 T2-3 B17 A110 T2-4 B17 A2 T2-5 B17 A2 T2-4 B17 A5 T2-5 B17 A5 T2-4 B17 A35 T2-5 B17 A35 T2-4 B17 A37 T2-5 B17 A37 T2-4 B17 A45 T2-5 B17 A45 T2-4 B17 A46 T2-5 B17 A46 T2-4 B17 A49 T2-5 B17 A49 T2-4 B17 A54 T2-5 B17 A54 T2-4 B17 A66 T2-5 B17 A66 T2-4 B17 A67 T2-5 B17 A67 T2-4 B17 A68 T2-5 B17 A68 T2-4 B17 A69 T2-5 B17 A69 T2-4 B17 A70 T2-5 B17 A70 T2-4 B17 A76 T2-5 B17 A76 T2-4 B17 A77 T2-5 B17 A77 T2-4 B17 A78 T2-5 B17 A78 T2-4 B17 A106 T2-5 B17 A106 T2-4 B17 A110 T2-5 B17 A110 T5-1 B17 A2 T7-1 B17 A2 T5-1 B17 A5 T7-1 B17 A5 T5-1 B17 A35 T7-1 B17 A35 T5-1 B17 A37 T7-1 B17 A37 T5-1 B17 A45 T7-1 B17 A45 T5-1 B17 A46 T7-1 B17 A46 T5-1 B17 A49 T7-1 B17 A49 T5-1 B17 A54 T7-1 B17 A54 T5-1 B17 A66 T7-1 B17 A66 T5-1 B17 A67 T7-1 B17 A67 T5-1 B17 A68 T7-1 B17 A68 T5-1 B17 A69 T7-1 B17 A69 T5-1 B17 A70 T7-1 B17 A70 T5-1 B17 A76 T7-1 B17 A76 T5-1 B17 A77 T7-1 B17 A77 T5-1 B17 A78 T7-1 B17 A78 T5-1 B17 A106 T7-1 B17 A106 T5-1 B17 A110 T7-1 B17 A110

Table 21

Tl-1 B24 A2 T2-1 B24 A2 Tl-1 B24 A5 T2-1 B24 A5 Tl-1 B24 A35 T2-1 B24 A35 Tl-1 B24 A37 T2-1 B24 A37 Tl-1 B24 A45 T2-1 B24 A45 Tl-1 B24 A46 T2-1 B24 A46 Tl-1 B24 A49 T2-1 B24 A49 Tl-1 B24 A54 T2-1 B24 A54 Tl-1 B24 A66 T2-1 B24 A66 Tl-1 B24 A67 T2-1 B24 A67 Tl-1 B24 A68 T2-1 B24 A68 Tl-1 B24 A69 T2-1 B24 A69 Tl-1 B24 A70 T2-1 B24 A70 Tl-1 B24 A76 T2-1 B24 A76 Tl-1 B24 A77 T2-1 B24 A77 Tl-1 B24 A78 T2-1 B24 A78 Tl-1 B24 A106 T2-1 B24 A106 Tl-1 B24 AllO T2-1 B24 AllO T2-2 B24 A2 T2-3 B24 A2 T2-2 B24 A5 T2-3 B24 A5 T2-2 B24 A35 T2-3 B24 A35 T2-2 B24 A37 T2-3 B24 A37 T2-2 B24 A45 T2-3 B24 A45 T2-2 B24 A46 T2-3 B24 A46 T2-2 B24 A49 T2-3 B24 A49 T2-2 B24 A54 T2-3 B24 A54 T2-2 B24 A66 T2-3 B24 A66 T2-2 B24 A67 T2-3 B24 A67 T2-2 B24 A68 T2-3 B24 A68 T2-2 B24 A69 T2-3 B24 A69 T2-2 B24 A70 T2-3 B24 A70 T2-2 B24 A76 T2-3 B24 A76 T2-2 B24 A77 T2-3 B24 A77 T2-2 B24 A78 T2-3 B24 A78 T2-2 B24 A106 T2-3 B24 A106 T2-2 B24 AllO T2-3 B24 AllO T2-4 B24 A2 T2-5 B24 A2 T2-4 B24 A5 T2-5 B24 A5 T2-4 B24 A35 T2-5 B24 A35 T2-4 B24 A37 T2-5 B24 A37 T2-4 B24 A45 T2-5 B24 A45 T2-4 B24 A46 T2-5 B24 A46 T2-4 B24 A49 T2-5 B24 A49

Table 22

T2-4 B24 A54 T2-5 B24 A54 T2-4 B24 A66 T2-5 B24 A66 T2-4 B24 A67 T2-5 B24 A67 T2-4 B24 A68 T2-5 B24 A68 T2-4 B24 A69 T2-5 B24 A69 T2-4 B24 A70 T2-5 B24 A7O T2-4 B24 A76 T2-5 B24 A76 T2-4 B24 A77 T2-5 B24 A77 T2-4 B24 A78 T2-5 B24 A78 T2-4 B24 A106 T2-5 B24 A106 T2-4 B24 A110 T2-5 B24 A11O T5-1 B24 A2 T7-1 B24 A2 T5-1 B24 A5 T7-1 B24 A5 T5-1 B24 A35 T7-1 B24 A35 T5-1 B24 A37 T7-1 B24 A37 T5-1 B24 A45 T7-1 B24 A45 T5-1 B24 A46 T7-1 B24 A46 T5-1 B24 A49 T7-1 B24 A49 T5-1 B24 A54 T7-1 B24 A54 T5-1 B24 A66 T7-1 B24 A66 T5-1 B24 A67 T7-1 B24 A67 T5-1 B24 A68 T7-1 B24 A68 T5-1 B24 A69 T7-1 B24 A69 T5-1 B24 A70 T7-1 B24 A70 T5-1 B24 A76 T7-1 B24 A76 T5-1 B24 A77 T7-1 B24 A77 T5-1 B24 A78 T7-1 B24 A78 T5-1 B24 A106 T7-1 B24 A106 T5-1 B24 A11O T7-1 B24 A11O Tl-1 B28 A2 T2-1 B28 A2 Tl-1 B28 A5 T2-1 B28 A5 Tl-1 B28 A35 T2-1 B28 A35 Tl-1 B28 A37 T2-1 B28 A37 Tl-1 B28 A45 T2-1 B28 A45 Tl-1 B28 A46 T2-1 B28 A46 Tl-1 B28 A49 T2-1 B28 A49 Tl-1 B28 A54 T2-1 B28 A54 Tl-1 B28 A66 T2-1 B28 A66 Tl-1 B28 A67 T2-1 B28 A67 Tl-1 B28 A68 T2-1 B28 A68 Tl-1 B28 A69 T2-1 B28 A69 Tl-1 B28 A70 T2-1 B28 A70 Tl-1 B28 A76 T2-1 B28 A76

Table 23 • ·

I ·

449 4

Tl-1 B28 A77 T2-1 B28 A77 Tl-1 B28 A78 T2-1 B28 A78 Tl-1 B28 A106 T2-1 B28 A106 Tl-1 B28 A110 T2-1 B28 A110 T2-2 B28 A2 T2-3 B28 A2 T2-2 B28 A5 T2-3 B28 A5 T2-2 B28 A35 T2-3 B28 A35 T2-2 B28 A37 T2-3 B28 A37 T2-2 B28 A45 T2-3 B28 A45 T2-2 B28 A46 T2-3 B28 A46 T2-2 B28 A49 T2-3 B28 A49 T2-2 B28 A54 T2-3 B28 A54 T2-2 B28 A66 T2-3 B28 A66 T2-2 B28 A67 T2-3 B28 A67 T2-2 B28 A68 T2-3 B28 A68 T2-2 B28 A69 T2-3 B28 A69 T2-2 B28 A70 T2-3 B28 A70 T2-2 B28 A76 T2-3 B28 A76 T2-2 B28 A77 T2-3 B28 A77 T2-2 B28 A78 T2-3 B28 A78 T2-2 B28 A106 T2-3 B28 A106 T2-2 B28 A110 T2-3 B28 A110 T2-4 B28 A2 T2-5 B28 A2 T2-4 B28 A5 T2-5 B28 A5 T2-4 B28 A35 T2-5 B28 A35 T2-4 B28 A37 T2-5 B28 A37 T2-4 B28 A45 T2-5 B28 A45 T2-4 B28 A46 T2-5 B28 A46 T2-4 B28 A49 T2-5 B28 A49 T2-4 B28 A54 T2-5 B28 A54 T2-4 B28 A66 T2-5 B28 A66 T2-4 B28 A67 T2-5 B28 A67 T2-4 B28 A68 T2-5 B28 A68 T2-4 B28 A69 T2-5 B28 A69 T2-4 B28 A70 T2-5 B28 A70 T2-4 B28 A76 T2-5 B28 A76 T2-4 B28 A77 T2-5 B28 A77 T2-4 B28 A78 T2-5 B28 A78 T2-4 B28 A106 T2-5 B28 A106 T2-4 B28 A110 T2-5 B28 A110 T5-1 B28 A2 T7-1 B28 A2 T5-1 B28 A5 T7-1 B28 A5 T5-1 B28 A35 T7-1 B28 A35

Table 24 titi titi ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti

100 ALIGN!

T5-1 B28 A37 T7-1 B28 A37 T5-1 B28 A45 T7-1 B28 A45 T5-1 B28 A46 T7-1 B28 A46 T5-1 B28 A49 T7-1 B28 A49 T5-1 B28 A54 T7-1 B28 A54 T5-1 B28 A66 T7-1 B28 A66 T5-1 B28 A67 T7-1 B28 A67 T5-1 B28 A68 T7-1 B28 A68 T5-1 B28 A69 T7-1 B28 A69 T5-1 B28 A70 T7-1 B28 A70 T5-1 B28 A76 T7-1 B28 A76 T5-1 B28 A77 T7-1 B28 A77 T5-1 B28 A78 T7-1 B28 A78 T5-1 B28 A106 T7-1 B28 A106 T5-1 B28 A110 T7-1 B28 A110 Tl-1 B29 A2 T2-1 B29 A2 Tl-1 B29 A5 T2-1 B29 A5 Tl-1 B29 A35 T2-1 B29 A35 Tl-1 B29 A37 T2-1 B29 A37 Tl-1 B29 A45 T2-1 B29 A45 Tl-1 B29 A46 T2-1 B29 A46 Tl-1 B29 A49 T2-1 B29 A49 Tl-1 B29 A54 T2-1 B29 A54 Tl-1 B29 A66 T2-1 B29 A66 Tl-1 B29 A67 T2-1 B29 A67 Tl-1 B29 A68 T2-1 B29 A68 Tl-1 B29 A69 T2-1 B29 A69 Tl-1 B29 A70 T2-1 B29 A70 Tl-1 B29 A76 T2-1 B29 A76 Tl-1 B29 A77 T2-1 B29 A77 Tl-1 B29 A78 T2-1 B29 A78 Tl-1 B29 A106 T2-1 B29 A106 Tl-1 B29 A110 | T2-1 B29 A110 T2-2 B29 A2 T2-3 B29 A2 T2-2 B29 A5 T2-3 B29 A5 T2-2 B29 A35 T2-3 B29 A35 T2-2 B29 A37 T2-3 B29 A37 T2-2 B29 A45 T2-3 B29 A45 T2-2 B29 A46 T2-3 B29 A46 T2-2 B29 A49 T2-3 B29 A49 T2-2 B29 A54 T2-3 B29 A54 T2-2 B29 A66 T2-3 B29 A66 T2-2 B29 A67 T2-3 B29 A67

• ·

Table 25

9 9 99 99 999 «• 99 ·· · · · · · 9 9 99 99 99 99 • 9 · 9 9 9 9 9 9

99999 ·· 9 ·· 99

101

-22-2 Β29 Α68 T2-3 B29 A68 -22-2 Β29 Α69 T2-3 B29 A69 -22-2 Β29 Α70 T2-3 B29 A70 -22-2 Β29 Α76 T2-3 B29 A76 -22-2 Β29 Α77 T2-3 B29 A77 -22-2 Β29 Α78 T2-3 B29 A78 -22-2 Β29 Α106 T2-3 B29 A106 -22-2 Β29 Α110 T2-3 B29 A110 Τ2-4 Β29 A2 T2-5 B29 A2 Τ2-4 Β29 A5 T2-5 B29 A5 Τ2-4 Β29 A35 T2-5 B29 A35 Τ2-4 Β29 A37 T2-5 B29 A37 Τ2-4 Β29 A45 T2-5 B29 A45 Τ2-4 Β29 A46 T2-5 B29 A46 Τ2-4 Β29 A49 T2-5 B29 A49 Τ2-4 Β29 A54 T2-5 B29 A54 Τ2-4 Β29 A66 T2-5 B29 A66 Τ2-4 Β29 A67 T2-5 B29 A67 Τ2-4 Β29 A68 T2-5 B29 A68 Τ2-4 Β29 A69 T2-5 B29 A69 Τ2-4 Β29 A70 T2-5 B29 A70 Τ2-4 Β29 A76 T2-5 B29 A76 Τ2-4 Β29 A77 T2-5 B29 A77 Τ2-4 Β29 A78 T2-5 B29 A78 Τ2-4 Β29 A106 T2-5 B29 A106 Τ2-4 Β29 A110 T2-5 B29 A110 -15-1 Β29 A2 T7-1 B29 A2 -15-1 Β29 A5 T7-1 B29 A5 -15-1 Β29 A35 T7-1 B29 A35 -15-1 Β29 A37 T7-1 B29 A37 -15-1 Β29 A45 T7-1 B29 A45 -15-1 Β29 A46 T7-1 B29 A46 -15-1 Β29 A49 T7-1 B29 A49 -15-1 Β29 A54 T7-1 B29 A54 -15-1 Β29 A66 T7-1 B29 A66 -15-1 Β29 A67 T7-1 B29 A67 -15-1 Β29 A68 T7-1 B29 A68 -15-1 Β29 A69 T7-1 B29 A69 -15-1 Β29 A70 T7-1 B29 A70 -15-1 Β29 A76 T7-1 B29 A76 -15-1 Β29 A77 T7-1 B29 A77 -15-1 Β29 A78 T7-1 B29 A78 -15-1 Β29 A106 T7-1 B29 A106

Table 26 φ • φ φ φ φ φ φ φ φ φ φ · · · φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ

102

-15-1 Β29 Α110 Τ7-1 Β29 Α110 -11-1 Β30 Α2 -12-1 Β30 Α2 -11-1 Β30 Α5 -12-1 Β30 Α5 -11-1 Β30 Α35 -12-1 Β30 Α35 -11-1 Β30 Α37 -12-1 Β30 Α37 -11-1 Β30 Α45 -12-1 Β30 Α45 -11-1 Β30 Α46 -12-1 Β30 Α46 -11-1 Β30 Α49 -12-1 Β30 Α49 -11-1 Β30 Α54 -12-1 Β30 Α54 -11-1 Β30 Α66 -12-1 Β30 Α66 -11-1 Β30 Α67 -12-1 Β30 Α67 -11-1 Β30 Α68 -12-1 Β30 Α68 -11-1 Β30 Α69 -12-1 Β30 Α69 -11-1 Β30 Α70 -12-1 Β30 Α70 -11-1 Β30 Α76 -12-1 Β30 Α76 -11-1 Β30 Α77 -12-1 Β30 Α77 -11-1 Β30 Α78 -12-1 Β30 Α78 -11-1 Β30 Α106 -12-1 Β30 Α106 -11-1 Β30 Α110 -12-1 Β30 Α110 -22-2 Β30 Α2 -2-3 Β30 Α2 -22-2 Β30 Α5 -2-3 Β30 Α5 -22-2 Β30 Α35 -2-3 Β30 Α35 -22-2 Β30 Α37 -2-3 Β30 Α37 -22-2 Β30 Α45 -2-3 Β30 Α45 -22-2 Β30 Α46 -2-3 Β30 Α46 -22-2 Β30 Α49 -2-3 Β30 Α49 -22-2 Β30 Α54 -2-3 Β30 Α54 -22-2 Β30 Α66 -2-3 Β30 Α66 -22-2 Β30 Α67 -2-3 Β30 Α67 -22-2 Β30 Α68 -2-3 Β30 Α68 -22-2 Β30 Α69 -2-3 Β30 Α69 -22-2 Β30 Α70 -2-3 Β30 Α70 -22-2 Β30 Α76 -2-3 Β30 Α76 -22-2 Β30 Α77 -2-3 Β30 Α77 -22-2 Β30 Α78 -2-3 Β30 Α78 -22-2 Β30 Α106 -2-3 Β30 Α106 -22-2 Β30 Α110 -2-3 Β30 Α110 Τ2-4 Β30 Α2 -52-5 Β30 Α2 Τ2-4 Β30 Α5 -52-5 Β30 Α5 Τ2-4 Β30 Α35 -52-5 Β30 Α35 Τ2-4 Β30 Α37 -52-5 Β30 Α37 Τ2-4 Β30 Α45 -52-5 Β30 Α45 Τ2-4 Β30 Α46 -52-5 Β30 Α46

Table 27 Φ «« «· φ φ · · · · · · · · φ φ φ φ

• · · «φφ φφ

103

Τ2-4 Β30 Α49 -52-5 Β30 Α49 Τ2-4 Β30 Α54 -52-5 Β30 Α54 Τ2-4 Β30 Α66 -52-5 Β30 Α66 Τ2-4 Β30 Α67 -52-5 Β30 Α67 Τ2-4 Β30 Α68 -52-5 Β30 Α68 Τ2-4 Β30 Α69 -52-5 Β30 Α69 Τ2-4 Β30 Α70 -52-5 Β30 Α70 Τ2-4 Β30 Α76 -52-5 Β30 Α76 Τ2-4 Β30 Α77 -52-5 Β30 Α77. Τ2-4 Β30 Α78 -52-5 Β30 Α78 Τ2-4 Β30 Α106 -52-5 Β30 Α106 Τ2-4 Β30 Α110 -52-5 Β30 Α110 -15-1 Β30 Α2 -17-1 Β30 Α2 -15-1 Β30 Α5 -17-1 Β30 Α5 -15-1 Β30 Α35 -17-1 Β30 Α35 -15-1 Β30 Α37 -17-1 Β30 Α37 -15-1 Β30 Α45 -17-1 Β30 Α45 -15-1 Β30 Α46 -17-1 Β30 Α46 -15-1 Β30 Α49 -17-1 Β30 Α49 -15-1 Β30 Α54 -17-1 Β30 Α54 -15-1 Β30 Α66 -17-1 Β30 Α66 -15-1 Β30 Α67 -17-1 Β30 Α67 -15-1 Β30 Α68 -17-1 Β30 Α68 -15-1 Β30 Α69 -17-1 Β30 Α69 -15-1 Β30 Α70 -17-1 Β30 Α70 -15-1 Β30 Α76 -17-1 Β30 Α76 -15-1 Β30 Α77 -17-1 Β30 Α77 -15-1 Β30 Α78 -17-1 Β30 Α78 -15-1 Β30 Α106 -17-1 Β30 Α106 -15-1 Β30 Α110 -17-1 Β30 Α110 -11-1 Β31 Α2 -12-1 Β31 Α2 -11-1 Β31 Α5 -12-1 Β31 Α5 -11-1 Β31 Α35 -12-1 Β31 Α35 -11-1 Β31 Α37 -12-1 Β31 Α37 -11-1 Β31 Α45 -12-1 Β31 Α45 -11-1 Β31 Α46 -12-1 Β31 Α46 -11-1 Β31 Α49 -12-1 Β31 Α49 -11-1 Β31 Α54 -12-1 Β31 Α54 -11-1 Β31 Α66 -12-1 Β31 Α66 -11-1 Β31 Α67 -12-1 Β31 Α67 -11-1 Β31 Α68 -12-1 Β31 Α68 -11-1 Β31 Α69 -12-1 Β31 Α69 -11-1 Β31 Α70 -12-1 Β31 Α70

> 0 0 4 (· 0 <

«0

104

Table 28

Tl-1 B31 A76 T2-1 B31 A76 Tl-1 B31 A77 T2-1 B31 A77 Tl-1 B31 A78 T2-1 B31 A78 Tl-1 B31 A106 T2-1 B31 A106 Tl-1 B31 AllO T2-1 B31 AllO T2-2 B31 A2 T2-3 B31 A2 T2-2 B31 A5 T2-3 B31 A5 T2-2 B31 A35 T2-3 B31 A35 T2-2 B31 A37 T2-3 B31 A37 T2-2 B31 A45 T2-3 B31 A45 T2-2 B31 A46 T2-3 B31 A46 T2-2 B31 A49 T2-3 B31 A49 T2-2 B31 A54 T2-3 B31 A54 T2-2 B31 A66 T2-3 B31 A66 T2-2 B31 A67 T2-3 B31 A67 T2-2 B31 A68 T2-3 B31 A68 T2-2 B31 A69 T2-3 B31 A69 T2-2 B31 A70 T2-3 B31 A70 T2-2 B31 A76 T2-3 B31 A76 T2-2 B31 A77 T2-3 B31 A77 T2-2 B31 A78 T2-3 B31 A78 T2-2 B31 A106 T2-3 B31 A106 T2-2 B31 AllO T2-3 B31 AllO T2-4 B31 A2 T2-5 B31 A2 T2-4 B31 A5 T2-5 B31 A5 T2-4 B31 A35 T2-5 B31 A35 T2-4 B31 A37 T2-5 B31 A37 T2-4 B31 A45 T2-5 B31 A45 T2-4 B31 A46 T2-5 B31 A46 T2-4 B31 A49 T2-5 B31 A49 T2-4 B31 A54 T2-5 B31 A54 T2-4 B31 A66 T2-5 B31 A66 T2-4 B31 A67 T2-5 B31 A67 T2-4 B31 A68 T2-5 B31 A68 T2-4 B31 A69 T2-5 B31 A69 T2-4 B31 A70 T2-5 B31 A70 T2-4 B31 A76 T2-5 B31 A76 T2-4 B31 A77 T2-5 B31 A77 T2-4 B31 A78 T2-5 B31 A78 T2-4 B31 A106 T2-5 B31 A106 T2-4 B31 AllO T2-5 B31 AllO T5-1 B31 A2 T7-1 B31 A2 T5-1 B31 A5 T7-1 B31 A5

4 * ····

Table 29

444 ···

444

4 4

9 9

9 ·· Μ • 4 9 9

9 9 9 4

4 4 4

105

-15-1 B31 A35 T7-1 B31 A35 -15-1 B31 A37 T7-1 B31 A37 -15-1 B31 A45 T7-1 B31 A45 -15-1 B31 A46 T7-1 B31 A46 -15-1 B31 A49 T7-1 B31 A49 -15-1 B31 A54 T7-1 B31 A54 -15-1 B31 A66 T7-1 B31 A66 -15-1 B31 A67 T7-1 B31 A67 -15-1 B31 A68 T7-1 B31 A68 -15-1 B31 A69 T7-1 B31 A69 -15-1 B31 A70 T7-1 B31 A70 -15-1 B31 A76 T7-1 B31 A76 -15-1 B31 A77 T7-1 B31 A77 -15-1 B31 A78 T7-1 B31 A78 -15-1 B31 A106 T7-1 B31 A106 -15-1 B31 A11O T7-1 B31 A110 Tl-1 B32 A2 T2-1 B32 A2 Tl-1 B32 A5 T2-1 B32 A5 Tl-1 B32 A35 T2-1 B32 A35 Tl-1 B32 A37 T2-1 B32 A37 Tl-1 B32 A45 T2-1 B32 A45 Tl-1 B32 A46 T2-1 B32 A46 Tl-1 B32 A49 T2-1 B32 A49 Tl-1 B32 A54 T2-1 B32 A54 Tl-1 B32 A66 T2-1 B32 A66 Tl-1 B32 A67 T2-1 B32 A67 Tl-1 B32 A68 T2-1 B32 A68 Tl-1 B32 A69 T2-1 B32 A69 Tl-1 B32 A70 T2-1 B32 A70 Tl-1 B32 A76 T2-1 B32 A76 Tl-1 B32 A77 T2-1 B32 A77 Tl-1 B32 A78 T2-1 B32 A78 Tl-1 B32 A106 T2-1 B32 A106 Tl-1 B32 A110 T2-1 B32 A110 T2-2 B32 A2 T2-3 B32 A2 T2-2 B32 A5 T2-3 B32 A5 T2-2 B32 A35 T2-3 B32 A35 T2-2 B32 A37 T2-3 B32 A37 T2-2 B32 A45 T2-3 B32 A45 T2-2 B32 A46 T2-3 B32 A46 T2-2 B32 A49 T2-3 B32 A49 T2-2 B32 A54 T2-3 B32 A54 T2-2 B32 A66 T2-3 B32 A66

106

Table 30

T2-2 B32 A67 T2-3 B32 A67 T2-2 B32 A68 T2-3 B32 A68 T2-2 B32 A69 T2-3 B32 A69 T2-2 B32 A70 T2-3 B32 A70 T2-2 B32 A76 T2-3 B32 A76 T2-2 B32 A77 T2-3 B32 A77 T2-2 B32 A78 T2-3 B32 A78 T2-2 B32 A106 T2-3 B32 A106 T2-2 B32 A110 T2-3 B32 A110 T2-4 B32 A2 T2-5 B32 A2 T2-4 B32 A5 T2-5 B32 A5 T2-4 B32 A35 T2-5 B32 A35 T2-4 B32 A37 T2-5 B32 A37 T2-4 B32 A45 T2-5 B32 A45 T2-4 B32 A46 T2-5 B32 A46 T2-4 B32 A49 T2-5 B32 A49 T2-4 B32 A54 T2-5 B32 A54 T2-4 B32 A66 T2-5 B32 A66 T2-4 B32 A67 T2-5 B32 A67 T2-4 B32 A68 T2-5 B32 A68 T2-4 B32 A69 T2-5 B32 A69 T2-4 B32 A70 T2-5 B32 A70 T2-4 B32 A76 T2-5 B32 A76 T2-4 B32 A77 T2-5 B32 A77 T2-4 B32 A78 T2-5 B32 A78 T2-4 B32 A106 T2-5 B32 A106 T2-4 B32 A110 T2-5 B32 A110 T5-1 B32 A2 T7-1 B32 A2 T5-1 B32 A5 T7-1 B32 A5 T5-1 B32 A35 T7-1 B32 A35 T5-1 B32 A37 T7-1 B32 A37 T5-1 B32 A45 T7-1 B32 A45 T5-1 B32 A46 T7-1 B32 A46 T5-1 B32 A49 T7-1 B32 A49 T5-1 B32 A54 T7-1 B32 A54 T5-1 B32 A66 T7-1 B32 A66 T5-1 B32 A67 T7-1 B32 A67 T5-1 B32 A68 T7-1 B32 A68 T5-1 B32 A69 T7-1 B32 A69 T5-1 B32 A70 T7-1 B32 A70 T5-1 B32 A76 T7-1 B32 A76 T5-1 B32 A77 T7-1 B32 A77 T5-1 B32 A78 T7-1 B32 A78

• · · ·

107

Table 31 • * · • ··· ·

T5-1 B32 A106 T7-1 B32 A106 T5-1 B32 A110 T7-1 B32 A110 Tl-1 B33 A2 T2-1 B33 A2 Tl-1 B33 A5 T2-1 B33 A5 Tl-1 B33 A35 T2-1 B33 A35 Tl-1 B33 A37 T2-1 B33 A37 Tl-1 B33 A45 T2-1 B33 A45 Tl-1 B33 A46 T2-1 B33 A46 Ti-i B33 A49 T2-1 B33 A49 Tl-1 B33 A54 T2-1 B33 A54 Tl-1 B33 A66 T2-1 B33 A66 Tl-1 B33 A67 T2-1 B33 A67 Tl-1 B33 A68 T2-1 B33 A68 Tl-1 B33 A69 T2-1 B33 A69 Tl-1 B33 A70 T2-1 B33 A70 Tl-1 B33 A76 T2-1 B33 A76 Tl-1 B33 A77 T2-1 B33 A77 Tl-1 B33 A78 T2-1 B33 A78 Tl-1 B33 A106 T2-1 B33 A106 Tl-1 B33 A110 T2-1 B33 A110 T2-2 B33 A2 T2-3 B33 A2 T2-2 B33 A5 T2-3 B33 A5 T2-2 B33 A35 T2-3 B33 A35 T2-2 B33 A37 T2-3 B33 A37 T2-2 B33 A45 T2-3 B33 A45 T2-2 B33 A46 T2-3 B33 A46 T2-2 B33 A49 T2-3 B33 A49 T2-2 B33 A54 T2-3 B33 A54 T2-2 B33 A66 T2-3 B33 A66 T2-2 B33 A67 T2-3 B33 A67 T2-2 B33 A68 T2-3 B33 A68 T2-2 B33 A69 T2-3 B33 A69 T2-2 B33 A70 T2-3 B33 A70 T2-2 B33 A76 T2-3 B33 A76 T2-2 B33 A77 T2-3 B33 A77 T2-2 B33 A78 T2-3 B33 A78 T2-2 B33 A106 T2-3 B33 A106 T2-2 B33 A110 T2-3 B33 A110 T2-4 B33 A2 T2-5 B33 A2 T2-4 B33 A5 T2-5 B33 A5 T2-4 B33 A35 T2-5 B33 A35 T2-4 B33 A37 T2-5 B33 A37 T2-4 B33 A45 T2-5 B33 A45

108

Table 32

T2-4 B33 A46 T2-5 B33 A46 T2-4 B33 A49 T2-5 B33 A49 T2-4 B33 A54 T2-5 B33 A54 T2-4 B33 A66 T2-5 B33 A66 T2-4 B33 A67 T2-5 B33 A67 T2-4 B33 A68 T2-5 B33 A68 T2-4 B33 A69 T2-5 B33 A69 T2-4 B33 A7O T2-5 B33 A70 T2-4 B33 A76 T2-5 B33 A76 T2-4 B33 A77 T2-5 B33 A77 T2-4 B33 A78 T2-5 B33 A78 T2-4 B33 A106 T2-5 B33 A106 T2-4 B33 A110 T2-5- B33 A110 T5-1 B33 A2 T7-1 B33 A2 T5-1 B33 A5 T7-1 B33 A5 T5-1 B33 A35 T7-1 B33 A35 T5-1 B33 A37 T7-1 B33 A37 T5-1 B33 A45 T7-1 B33 A45 T5-1 B33 A46 T7-1 B33 A46 T5-1 B33 A49 T7-1 B33 A49 T5-1 B33 A54 T7-1 B33 A54 T5-1 B33 A66 T7-1 B33 A66 T5-1 B33 A67 T7-1 B33 A67 T5-1 B33 A68 T7-1 B33 A68 T5-1 B33 A69 T7-1 B33 A69 T5-1 B33 A70 T7-1 B33 A70 T5-1 B33 A76 T7-1 B33 A76 T5-1 B33 A77 T7-1 B33 A77 T5-1 B33 A78 T7-1 B33 A78 T5-1 B33 A106 T7-1 B33 A106 T5-1 B33 A110 T7-1 B33 A110 Tl-1 B34 A2 T2-1 B34 A2 Tl-1 B34 A5 T2-1 B34 A5 Tl-1 B34 A35 T2-1 B34 A35 Tl-1 B34 A37 T2-1 B34 A37 Tl-1 B34 A45 T2-1 B34 A45 Tl-1 B34 A46 T2-1 B34 A46 Tl-1 B34 A49 T2-1 B34 A49 Tl-1 B34 A54 T2-1 B34 A54 Tl-1 B34 A66 T2-1 B34 A66 Tl-1 B34 A67 T2-1 B34 A67 Tl-1 B34 A68 | T2-1 B34 A68 Tl-1 B34 A69 I T2-1 B34 A69

109

Table 33

Tl-1 B34 A70 T2-1 B34 A70 Tl-1 B34 A76 T2-1 B34 A76 Tl-1 B34 A77 T2-1 B34 A77 Tl-1 B34 A78 T2-1 B34 A78 Tl-1 B34. A106 T2-1 B34 A106 Tl-1 B34 AllO T2-1 B34 AllO T2-2 B34 A2 T2-3 B34 A2 T2-2 B34 A5 T2-3 B34 A5 T2-2 B34 A35 T2-3 B34 A35 T2-2 B34 A37 T2-3 B34 A37 T2-2 B34 A45 T2-3 B34 A45 T2-2 B34 A46 T2-3 B34 A46 T2-2 B34 A49 T2-3 B34 A49 T2-2 B34 A54 T2-3 B34 A54 T2-2 B34 A66 T2-3 B34 A66 T2-2 B34 A67 T2-3 B34 A67 T2-2 B34 A68 T2-3 B34 A68 T2-2 B34 A69 T2-3 B34 A69 T2-2 B34 A70 T2-3 B34 A70 T2-2 B34 A76 T2-3 B34 A76 T2-2 B34 A77 T2-3 B34 A77 T2-2 B34 A78 T2-3 B34 A78 T2-2 B34 A106 T2-3 B34 A106 T2-2 B34 AllO T2-3 B34 AllO T2-4 B34 A2 T2-5 B34 A2 T2-4 B34 A5 T2-5 B34 A5 T2-4 B34 A35 T2-5 B34 A35 T2-4 B34 A37 T2-5 B34 A37 T2-4 B34 A45 T2-5 B34 A45 T2-4 B34 A46 T2-5 B34 A46 T2-4 B34 A49 T2-5 B34 A49 T2-4 B34 A54 T2-5 B34 A54 T2-4 B34 A66 T2-5 B34 A66 T2-4 B34 A67 T2-5 B34 A67 T2-4 B34 A68 T2-5 B34 A68 T2-4 B34 A69 T2-5 B34 A69 T2-4 B34 A70 T2-5 B34 A70 T2-4 B34 A76 T2-5 B34 A76 T2-4 B34 A77 T2-5 B34 A77 T2-4 B34 A78 T2-5 B34 A78 T2-4 B34 A106 T2-5 B34 A106 T2-4 B34 AllO T2-5 B34 AllO

• ·

110

Table 34 • 4 · 4 · 4 ···

T5-1 B34 A2 T7-1 B34 A2 T5-1 B34 A5 T7-1 B34 A5 T5-1 B34 A35 T7-1 B34 A35 T5-1 B34 A37 T7-1 B34 A37 T5-1 B34 A45 T7-1 B34 A45 T5-1 B34 A46 T7-1 B34 A46 T5-1 B34 A49 T7-1 B34 A49 T5-1 B34 A54 T7-1 B34 A54 T5-1 B34 A66 T7-1 B34 A66 T5-1 B34 A67 T7-1 B34 A67 T5-1 B34 A68 T7-1 B34 A68 T5-1 B34 A69 T7-1 B34 A69 T5-1 B34 A70 T7-1 B34 A70 T5-1 B34 A76 T7-1 B34 A76 T5-1 B34 A77 T7-1 B34 A77 T5-1 B34 A78 T7-1 B34 A78 T5-1 B34 A106 T7-1 B34 A106 T5-1 B34 AllO T7-1 B34 AllO Tl-1 B35 A2 T2-1 B35 A2 Tl-1 B35 A5 T2-1 B35 A5 Tl-1 B35 A35 T2-1 B35 A35 Tl-1 B35 A37 T2-1 B35 A37 Tl-1 B35 A45 T2-1 B35 A45 Tl-1 B35 A46 T2-1 B35 A46 Tl-1 B35 A49 T2-1 B35 A49 Tl-1 B35 A54 T2-1 B35 A54 Tl-1 B35 A66 T2-1 B35 A66 Tl-1 B35 A67 T2-1 B35 A67 Tl-1 B35 A68 T2-1 B35 A68 Tl-1 B35 A69 T2-1 B35 A69 Tl-1 B35 A70 T2-1 B35 A70 Tl-1 B35 A76 T2-1 B35 A76 Tl-1 B35 A77 T2-1 B35 A77 Tl-1 B35 A78 T2-1 B35 A78 Tl-1 B35 A106 T2-1 B35 A106 Tl-1 B35 AllO T2-1 B35 AllO T2-2 B35. A2 T2-3 B35 A2 T2-2 B35 A5 T2-3 B35 A5 T2-2 B35 A35 T2-3 B35 A35 T2-2 B35 A37 T2-3 B35 A37 T2-2 B35 A45 T2-3 B35 A45 T2-2 B35 A46 T2-3 B35 A46 T2-2 B35 A49 T2-3 B35 A49

• · ··· ·

111

Table 35

T2-2 B35 A54 T2-3 B35 A54 T2-2 B35 A66 T2-3 B35 A66 T2-2 B35 A67 T2-3 B35 A67 T2-2 B35 A68 T2-3 B35 A68 T2-2 B35 A69 T2-3 B35 A69 T2-2 B35 A70 T2-3 B35 A70 T2-2 B35 A76 T2-3 B35 A76 T2-2 B35 A77 T2-3 B35 A77 T2-2 B35 A78 T2-3 B35 A78 T2-2 B35 A106 T2-3 B35 A106 T2-2 B35 A110 T2-3 B35 A110 T2-4 B35 A2 T2-5 B35 A2 T2-4 B35 A5 T2-5 B35 A5 T2-4 B35 A35 T2-5 B35 A35 T2-4 B35 A37 T2-5 B35 A37 T2-4 B35 A45 T2-5 B35 A45 T2-4 B35 A46 T2-5 B35 A46 T2-4 B35 A49 T2-5 B35 A49 T2-4 B35 A54 T2-5 B35 A54 T2-4 B35 A66 T2-5 B35 A66 T2-4 B35 A67 T2-5 B35 A67 T2-4 B35 A68 T2-5 B35 A68 T2-4 B35 A69 T2-5 B35 A69 T2-4 B35 A70 T2-5 B35 A70 T2-4 B35 A76 T2-5 B35 A76 T2-4 B35 A77 T2-5 B35 A77 T2-4 B35 A78 T2-5 B35 A78 T2-4 B35 A106 T2-5 B35 A106 T2-4 B35 A110 T2-5 B35 A110 T5-1 B35 A2 T7-1 B35 A2 T5-1 B35 A5 T7-1 B35 A5 T5-1 B35 A35 T7-1 B35 A35 T5-1 B35 A37 T7-1 B35 A37 T5-1 B35 A45 T7-1 B35 A45 T5-1 B35 A46 T7-1 B35 A46 T5-1 B35 A49 T7-1 B35 A49 T5-1 B35 A54 T7-1 B35 A54 T5-1 B35 A66 T7-1 B35 A66 T5-1 B35 A67 T7-1 B35 A67 T5-1 B35 A68 T7-1 B35 A68 T5-1 B35 A69 T7-1 B35 A69 T5-1 B35 A70 T7-1 B35 A70 T5-1 B35 A76 T7-1 B35 A76

112

Table 36 ·· 44 • * 4 • 4 • 4 4 4

4 4 4

44

T5-1 B35 A77 T7-1 B35 A77 T5-1 B35 A78 T7-1 B35 A78 T5-1 B35 A106 T7-1 B35 A106 T5-1 B35 AllO T7-1 B35 AllO Tl-1 B36 A2 T2-1 B36 A2 Tl-1 B36 A5 T2-1 B36 A5 Tl-1 B36 A35 T2-1 B36 A35 Tl-1 B36 A37 T2-1 B36 A37 Tl-1 B36 A45 T2-1 B36 A45 Tl-1 B36 A46 T2-1 B36 A46 Tl-1 B36 A49 T2-1 B36 A49 Tl-1 B36 A54 T2-1 B36 A54 Tl-1 B36 A66 T2-1 B36 A66 Tl-1 B36 A67 T2-1 B36 A67 Tl-1 B36 A68 T2-1 B36 A68 Tl-1 B36 A69 T2-1 B36 A69 Tl-1 B36 A7O T2-1 B36 A70 Tl-1 B36 A76 T2-1 B36 A76 Tl-1 B36 A77 T2-1 B36 A77 Tl-1 B36 A78 T2-1 B36 A78 Tl-1 B36 A106 T2-1 B36 A106 Tl-1 B36 AllO T2-1 B36 AllO T2-2 B36 A2 T2-3 B36 A2 T2-2 B36 A5 T2-3 B36 A5 T2-2 B36 A35 T2-3 B36 A35 T2-2 B36 A37 T2-3 B36 A37 T2-2 B36 A45 T2-3 B36 A45 T2-2 B36 A46 T2-3 B36 A46 T2-2 B36 A49 T2-3 B36 A49 T2-2 B36 A54 T2-3 B36 A54 T2-2 B36 A66 T2-3 B36 A66 T2-2 B36 A67 T2-3 B36 A67 T2-2 B36 A68 T2-3 B36 A68 T2-2 B36 A69 T2-3 B36 A69 T2-2 B36 A70 T2-3 B36 A70 T2-2 B36 A76 T2-3 B36 A76 T2-2 B36 A77 T2-3 B36 A77 T2-2 B36 A78 T2-3 B36 A78 T2-2 B36 A106 T2-3 B36 A106 T2-2 B36 AllO T2-3 B36 AllO T2-4 B36 A2 T2-5 B36 A2 T2-4 B36 A5 T2-5 B36 A5 T2-4 B36 A35-T2-5 B36 A35

113

Table 37

T2-4 B.36 A37 T2-5 B36 A37 T2-4 B36 A45 T2-5 B36 A45 T2-4 B36 A46 T2-5 B36 A46 T2-4 B36 A49 T2-5 B36 A49 T2-4 B36 A54 T2-5 B36 A54 T2-4 B36 A66 T2-5 B36 A66 T2-4 B36 A67 T2-5 B36 A67 T2-4 B36 A68 T2-5 B36 A68 T2-4 B36 A69 T2-5 B36 A69 T2-4 B36 A70 T2-5 B36 A7O T2-4 B36 A76 T2-5 B36 A76 T2-4 B36 A77 T2-5 B36 A77 T2-4 B36 A78 T2-5 B36 A78 T2-4 B36 A106 T2-5 B36 A106 T2-4 B36 A110 T2-5 B36 A11O T5-1 B36 A2 T7-1 B36 A2 T5-1 B36 A5 T7-1 B36 A5 T5-1 B36 A35 T7-1 B36 A35 T5-1 B36 A37 T7-1 B36 A37 T5-1 B36 A45 T7-1 B36 A45 T5-1 B36 A46 T7-1 B36 A46 T5-1 B36 A49 T7-1 B36 A49 T5-1 B36 A54 T7-1 B36 A54 T5-1 B36 A66 T7-1 B36 A66 T5-1 B36 A67 T7-1 B36 A67 T5-1 B36 A68 T7-1 B36 A68 T5-1 B36 A69 T7-1 B36 A69 T5-1 B36 A7O T7-1 B36 A70 T5-1 B36 A76 T7-1 B36 A76 T5-1 B36 A77 T7-1 B36 A77 T5-1 B36 A78 T7-1 B36 A78 T5-1 B36 A106 T7-1 B36 A106 T5-1 B36 A11O T7-1 B36 A11O Tl-1 B37 A2 T2-1 B37 A2 Tl-1 B37 A5 T2-1 B37 A5 Tl-1 B37 A35 T2-1 B37 A35 Tl-1 B37 A37 T2-1 B37 A37 Tl-1 B37 A45 T2-1 B37 A45 Tl-1 B37 A46 T2-1 B37 A46 Tl-1 B37 A49 T2-1 B37 A49 Tl-1 B37 A54 T2-1 B37 A54 Tl-1 B37 A66 T2-1 B37 A66 Tl-1 B37 A67 T2-1 B37 A67

114

Table 38 fcfc fcfc fcfc fcfc fcfc fcfc fcfc fcfc fcfc fcfc fcfc

Tl-1 B37 A68 T2-1 B37 A68 Tl-1 B37 A69 T2-1 B37 A69 Tl-1 B37 A70 T2-1 B37 A70 Tl-1 B37 A76 T2-1 B37 A76 Tl-1 B37 A77 T2-1 B37 A77 Tl-1 B37 A78 T2-1 B37 A78 Tl-1 B37 A106 T2-1 B37 A106 Tl-1 B37 AllO T2-1 B37 AllO T2-2 B37 A2 T2-3 B37 A2 T2-2 B37 A5 T2-3 B37 A5 T2-2 B37 A35 T2-3 B37 A35 T2-2 B37 A37 T2-3 B37 A37 T2-2 B37 A45 T2-3 B37 A45 T2-2 B37 A46 T2-3 B37 A46 T2-2 B37 A49 T2-3 B37 A49 T2-2 B37 A54 T2-3 B37 A54 T2-2 B37 A66 T2-3 B37 A66 T2-2 B37 A67 T2-3 B37 A67 T2-2 B37 A68 T2-3 B37 A68 T2-2 B37 A69 T2-3 B37 A69 T2-2 B37 A70 T2-3 B37 A7O T2-2 B37 A76 T2-3 B37 A76 T2-2 B37 A77 T2-3 B37 A77 T2-2 B37 A78 T2-3 B37 A78 T2-2 B37 A106 T2-3 B37 A106 T2-2 B37 AllO T2-3 B37 AllO T2-4 B37 A2 T2-5 B37 A2 T2-4 B37 A5 T2-5 B37 A5 T2-4 B37 A35 T2-5 B37 A35 T2-4 B37 A37 T2-5 B37 A37 T2-4 B37 A45 T2-5 B37 A45 T2-4 B37 A46 T2-5 B37 A46 T2-4 B37 A49 T2-5 B37 A49 T2-4 B37 A54 T2-5 B37 A54 T2-4 B37 A66 T2-5 B37 A66 T2-4 B37 A67 T2-5 B37 A67 T2-4 B37 A68 T2-5 B37 A68 T2-4 B37 A69 T2-5 B37 A69 T2-4 B37 A7O T2-5 B37 A7O T2-4 B37 A76 T2-5 B37 A76 T2-4 B37 A77 T2-5 B37 A77 T2-4 B37 A78 T2-5 B37 A78 T2-4 B37 A106 T2-5 B37 A106

Table 39

00 0 0 0

0 0 • 000 0 0

0 0 0 0 • i 000 0

0 0 0 0 0 0 0 0

115

T2-4 B37 AllO T2-5 B37 AllO T5-1 B37 A2 T7-1 B37 A2 T5-1 B37 A5 T7-1 B37 A5 T5-1 B37 A35 T7-1 B37 A35 T5-1 B37 A37 T7-1 B37 A37 T5-1 B37 A45 T7-1 B37 A45 T5-1 B37 A46 T7-1 B37 A46 T5-1 B37 A49 T7-1 B37 A49 T5-1 B37 A54 T7-1 B37 A54 T5-1 B37 A66 T7-1 B37 A66 T5-1 B37 A67 T7-1 B37 A67 T5-1 B37 A68 T7-1 B37 A68 T5-1 B37 A69 T7-1 B37 A69 T5-1 B37 A70 T7-1 B37 A70 T5-1 B37 A76 T7-1 B37 A76 T5-1 B37 A77 T7-1 B37 A77 T5-1 B37 A78 T7-1 B37 A78 T5-1 B37 A106 T7-1 B37 A106 T5-1 B37 AllO T7-1 B37 AllO Tl-1 B38 A2 T2-1 B38 A2 Tl-1 B38 A5 T2-1 B38 A5 Tl-1 B38 A35 T2-1 B38 A35 Tl-1 B38 A37 T2-1 B38 A37 Tl-1 B38 A45 T2-1 B38 A45 Tl-1 B38 A46 T2-1 B38 A46 Tl-1 B38 A49 T2-1 B38 A49 Tl-1 B38 A54 T2-1 B38 A54 Tl-1 B38 A66 T2-1 B38 A66 Tl-1 B38 A67 T2-1 B38 A67 Tl-1 B38 A68 T2-1 B38 A68 Tl-1 B38 A69 T2-1 B38 A69 Tl-1 B38 A70 T2-1 B38 A70 Tl-1 B38 A76 T2-1 B38 A76 Tl-1 B38 A77 T2-1 B38 A77 Tl-1 B38 A78 T2-1 B38 A78 Tl-1 B38 A106 T2-1 B38 A106 Tl-1 B38 AllO T2-1 B38 AllO T2-2 B38 A2 T2-3 B38 A2 T2-2 B38 A5 T2-3 B38 A5 T2-2 B38 A35 T2-3 B38 A35 T2-2 B38 A37 T2-3 B38 A37 T2-2 B38 A45 T2-3 B38 A45 T2-2 B38 A46 T2-3 B38 A46

• · · · ·

116

Table 40 ftft ftft ftft ftft

T2-2 B38 A49 T2-3 B38 A49 T2-2 B38 A54 T2-3 B38 A54 T2-2 B38 A66 T2-3 B38 A66 T2-2 B38 A67 T2-3 B38 A67 T2-2 B38 A68 T2-3 B38 A68 T2-2 B38 A69 T2-3 B38 A69 T2-2 B38 A70 T2-3 B38 A70 T2-2 B38 A76 T2-3 B38 A76 T2-2 B38 A77 T2-3 B38 A77 T2-2 B38 A78 T2-3 B38 A78 T2-2 B38 A106 T2-3 B38 A106 T2-2 B38 A110 T2-3 B38 A110 T2-4 B38 A2 T2-5 B38 A2 T2-4 B38 A5 T2-5 B38 A5 T2-4 B38 A35 T2-5 B38 A35 T2-4 B38 A37 T2-5 B38 A37 T2-4 B38 A45 T2-5 B38 A45 T2-4 B38 A46 T2-5 B38 A46 T2-4 B38 A49 T2-5 B38 A49 T2-4 B38 A54 T2-5 B38 A54 T2-4 B38 A66 T2-5 B38 A66 T2-4 B38 A67 T2-5 B38 A67 T2-4 B38 A68 T2-5 B38 A68 T2-4 B38 A69 T2-5 B38 A69 T2-4 B38 A70 T2-5 B38 A70 T2-4 B38 A76 T2-5 B38 A76 T2-4 B38 A77 T2-5 B38 A77 T2-4 B38 A78 T2-5 B38 A78 T2-4 B38 A106 T2-5 B38 A106 T2-4 B38 A110 T2-5 B38 A110 T5-1 B38 A2 T7-1 B38 A2 T5-1 B38 A5 T7-1 B38 A5 T5-1 B38 A35 T7-1 B38 A35 T5-1 B38 A37 T7-1 B38 A37 T5-1 B38 A45 T7-1 B38 A45 T5-1 B38 A46 T7-1 B38 A46 T5-1 B38 A49 T7-1 B38 A49 T5-1 B38 A54 T7-1 B38 A54 T5-1 B38 A66 T7-1 B38 A66 T5-1 B38 A67 T7-1 B38 A67 T5-1 B38 A68 T7-1 B38 A68 T5-1 B38 A69 T7-1 B38 A69 T5-1 B38 A70 T7-1 B38 A70

117

Table 41

99

9 9 9 9 9 • 999 99 9 • 9 9 9 9

998 99 99 9

9999

T5-1 B38 A76 T7-1 B38 A76 T5-1 B38 A77 T7-1 B38 A77 T5-1 B38 A78 T7-1 B38 A78 T5-1 B38 A106 T7-1 B38 A106 T5-1 B38 A110 T7-1 B38 A11O Tl-1 B39 A2 T2-1 B39 A2 Tl-1 B39 A5 T2-1 B39 A5 Tl-1 B39 A35 T2-1 B39 A35 Tl-1 B39 A37 T2-1 B39 A37 Tl-1 B39 A45 T2-1 B39 A45 Tl-1 B39 A46 T2-1 B39 A46 Tl-1 B39 A49 T2-1 B39 A49 Tl-1 B39 A54 T2-1 B39 A54 Tl-1 B39 A66 T2-1 B39 A66 Tl-1 B39 A67 T2-1 B39 A67 Tl-1 B39 A68 T2-1 B39 A68 Tl-1 B39 A69 T2-1 B39 A69 Tl-1 B39 A70 T2-1 B39 A7O Tl-1 B39 A76 T2-1 B39 A76 Tl-1 B39 A77 T2-1 B39 A77 Tl-1 B39 A78 T2-1 B39 A78 Tl-1 B39 A106 T2-1 B39 A106 Tl-1 B39 A11O T2-1 B39 A11O T2-2 B39 A2 T2-3 B39 A2 T2-2 B39 A5 T2-3 B39 A5 T2-2 B39 A35 T2-3 B39 A35 T2-2 B39 A37 T2-3 B39 A37 T2-2 B39 A45 T2-3 B39 A45 T2-2 B39 A46 T2-3 B39 A46 T2-2 B39 A49 T2-3 B39 A49 T2-2 B39 A54 T2-3 B39 A54 T2-2 B39 A66 T2-3 B39 A66 T2-2 B39 A67 T2-3 B39 A67 T2-2 B39 A68 T2-3 B39 A68 T2-2 B39 A69 T2-3 B39 A69 T2-2 B39 A70 T2-3 B39 A7O T2-2 B39 A76 T2-3 B39 A76 T2-2 B39 A77 T2-3 B39 A77 T2-2 B39 A78 T2-3 B39 A78 T2-2 B39 A106 T2-3 B39 A106 T2-2 B39 A11O T2-3 B39 A11O T2-4 B39 A2 T2-5 B39 A2

118

Table 42 • 9 9 * * · · · 42 42 42 42 42 42 42 42 42 42 42 42 42 42 42 42

T2-4 B39 A5 T2-5 B39 A5 T2-4 B39 A35 T2-5 B39 A35 T2-4 B39 A37 T2-5 B39 A37 T2-4 B39 A45 T2-5 B39 A45 T2-4 B39 A46 T2-5 B39 A46 T2-4 B39 A49 T2-5 B39 A49 T2-4 B39 A54 T2-5 B39 A54 T2-4 B39 A66 T2-5 B39 A66 T2-4 B39 A67 T2-5 B39 A67 T2-4 B39 A68 T2-5 B39 A68 T2-4 B39 A69 T2-5 B39 A69 T2-4 B39 A70 T2-5 B39 A70 T2-4 B39 A76 T2-5 B39 A76 T2-4 B39 A77 T2-5 B39 A77 T2-4 B39 A78 T2-5 B39 A78 T2-4 B39 A106 T2-5 B39 A106 T2-4 B39 A110 T2-5 B39 A11O T5-1 B39 A2 T7-1 B39 A2 T5-1 B39 A5 T7-1 B39 A5 T5-1 B39 A35 T7-1 B39 A35 T5-1 B39 A37 T7-1 B39 A37 T5-1 B39 A45 T7-1 B39 A45 T5-1 B39 A46 T7-1 B39 A46 T5-1 B39 A49 T7-1 B39 A49 T5-1 B39 A54 T7-1 B39 A54 T5-1 B39 A66 T7-1 B39 A66 T5-1 B39 A67 T7-1 B39 A67 T5-1 B39 A68 T7-1 B39 A68 T5-1 B39 A69 T7-1 B39 A69 T5-1 B39 A70 T7-1 B39 A70 T5-1 B39 A76 T7-1 B39 A76 T5-1 B39 A77 T7-1 B39 A77 T5-1 B39 A78 T7-1 B39 A78 T5-1 B39 A106 T7-1 B39 A106 T5-1 B39 A11O T7-1 B39 A11O Tl-1 B40 A2 T2-1 B40 A2 Tl-1 B40 A5 T2-1 B40 A5 Tl-1 B40 A35 T2-1 B40 A35 Tl-1 B40 A37 T2-1 B40 A37 Tl-1 B40 A45 T2-1 B40 A45 Tl-1 B40 A46 T2-1 B40 A46 Tl-1 B40 A49 T2-1 B40 A49

119

Table 43 • »W« · ·

Φ »

I · ft · · · φ φ φ »φ» »» ΦΦΦ ΦΦΦ ΦΦΦ ΦΦΦ ΦΦΦ ΦΦΦ

Φ Φ · ΦΦ

Tl-1 B40 A54 T2-1 B40 A54 Tl-1 B40 A66 T2-1 B40 A66 Tl-1 B40 A67 T2-1 B40 A67 Tl-1 B40 A68 T2-1 B40 A68 Tl-1 B40 A69 T2-1 B40 A69 Tl-1 B40 A70 T2-1 B40 A70 Tl-1 B40 A76 T2-1 B40 A76 Tl-1 B40 A77 T2-1 B40 A77 Tl-1 B40 A78 T2-1 B40 A78 Tl-1 B40 A106 T2-1 B40 A106 Tl-1 B40 A110 T2-1 B40 A110 T2-2 B40 A2 T2-3 B40 A2 T2-2 B40 A5 T2-3 B40 A5 T2-2 B40 A35 T2-3 B40 A35 T2-2 B40 A37 T2-3 B40 A37 T2-2 B40 A45 T2-3 B40 A45 T2-2 B40 A46 T2-3 B40 A46 T2-2 B40 A49 T2-3 B40 A49 T2-2 B40 A54 T2-3 B40 A54 T2-2 B40 A66 T2-3 B40 A66 T2-2 B40 A67 T2-3 B40 A67 T2-2 B40 A68 T2-3 B40 A68 T2-2 B40 A69 T2-3 B40 A69 T2-2 B40 A70 T2-3 B40 A70 T2-2 B40 A76 T2-3 B40 A76 T2-2 B40 A77 T2-3 B40 A77 T2-2 B40 A78 T2-3 B40 A78 T2-2 B40 A106 T2-3 B40 A106 T2-2 B40 A110 T2-3 B40 A110 T2-4 B40 A2 T2-5 B40 A2 T2-4 B40 A5 T2-5 B40 A5 T2-4 B40 A35 T2-5 B40 A35 T2-4 B40 A37 T2-5 B40 A37 T2-4 B40 A45 T2-5 B40 A45 T2-4 B40 A46 T2-5 B40 A46 T2-4 B40 A49 T2-5 B40 A49 T2-4 B40 A54 T2-5 B40 A54 T2-4 B40 A66 T2-5 B40 A66 T2-4 B40 A67 T2-5 B40 A67 T2-4 B40 A68 T2-5 B40 A68 T2-4 B40 A69 T2-5 B40 A69 T2-4 B40 A70 T2-5 B40 A70

120

Table 44

· » • v ·· »· • φ • » • · • • · • φ • φ E · «Φ • φ • · φ · φ φ « • « * · • · • • φ ·· ·· • φ · φφ

Τ2-4 Β40 Α76 -52-5 Β40 Α76 Τ2-4 Β40 Α77 -52-5 Β40 Α77 Τ2-4 Β40 Α78 -52-5 Β40 Α78 Τ2-4 Β40 Α106 -52-5 Β40 Α106 Τ2-4 Β40 Α110 -52-5 Β40 Α110 -15-1 Β40 Α2 -17-1 Β40 Α2 -15-1 Β40 Α5 -17-1 Β40 Α5 -15-1 Β40 Α35 -17-1 Β40 Α35 -15-1 Β40 Α37 -17-1 Β40 Α37 -15-1 Β40 Α45 -17-1 Β40 Α45 -15-1 Β40 Α46 -17-1 Β40 Α46 -15-1 Β40 Α49 -17-1 Β40 Α49 -15-1 Β40 Α54 -17-1 Β40 Α54 -15-1 Β40 Α66 -17-1 Β40 Α66 -15-1 Β40 Α67 -17-1 Β40 Α67 -15-1 Β40 Α68 -17-1 Β40 Α68 -15-1 Β40 Α69 -17-1 Β40 Α69 -15-1 Β40 Α7Ο -17-1 Β40 Α70 -15-1 Β40 Α76 -17-1 Β40 Α76 -15-1 Β40 Α77 -17-1 Β40 Α77 -15-1 Β40 Α78 -17-1 Β40 Α78 -15-1 Β40 Α106 -17-1 Β40 Α106 -15-1 Β40 Α110 -17-1 Β40 Α11Ο -11-1 Β41 Α2 -12-1 Β41 Α2 -11-1 Β41 Α5 -12-1 Β41 Α5 -11-1 Β41 Α35 -12-1 Β41 Α35 -11-1 Β41 Α37 -12-1 Β41 Α37 -11-1 Β41 Α45 -12-1 Β41 Α45 -11-1 Β41 Α46 -12-1 Β41 Α46 -11-1 Β41 Α49 -12-1 Β41 Α49 -11-1 Β41 Α54 -12-1 Β41 Α54 -11-1 Β41 Α66 -12-1 Β41 Α66 -11-1 Β41 Α67 -12-1 Β41 Α67 -11-1 Β41 Α68 -12-1 Β41 Α68 -11-1 Β41 Α69 -12-1 Β41 Α69 -11-1 Β41 Α70 -12-1 Β41 Α70 -11-1 Β41 Α76 -12-1 Β41 Α76 -11-1 Β41 Α77 -12-1 Β41 Α77 -11-1 Β41 Α78 -12-1 Β41 Α78 -11-1 Β41 Α106 -12-1 Β41 Α106 -11-1 Β41 Α110 -12-1 Β41 Α110

tic titi ··

121

Table 45 three ti three ti ti three ti ti three ti ti 9 ti 9 ti ti

T2-2 B41 A2 T2-3 B41 A2 T2-2 B41 A5 T2-3 B41 A5 T2-2 B41 A35 T2-3 B41 A35 T2-2 B41 A37 T2-3 B41 A37 T2-2 B41 A45 T2-3 B41 A45 T2-2 B41 A46 T2-3 B41 A46 T2-2 B41 A49 T2-3 B41 A49 T2-2 B41 A54 T2-3 B41 A54 T2-2 B41 A66 T2-3 B41 A66 T2-2 B41 A67 T2-3 B41 A67 T2-2 B41 A68 T2-3 B41 A68 T2-2 B41 A69 T2-3 B41 A69 T2-2 B41 A70 T2-3 B41 A70 T2-2 B41 A76 T2-3 B41 A76 T2-2 B41 A77 T2-3 B41 A77 T2-2 B41 A78 T2-3 B41 A78 T2-2 B41 A106 T2-3 B41 A106 T2-2 B41 A110 T2-3 B41 A11O T2-4 B41 A2 T2-5 B41 A2 T2-4 B41 A5 T2-5 B41 A5 T2-4 B41 A35 T2-5 B41 A35 T2-4 B41 A37 T2-5 B41 A37 T2-4 B41 A45 T2-5 B41 A45 T2-4 B41 A46 T2-5 B41 A46 T2-4 B41 A49 T2-5 B41 A49 T2-4 B41 A54 T2-5 B41 A54 T2-4 B41 A66 T2-5 B41 A66 T2-4 B41 A67 T2-5 B41 A67 T2-4 B41 A68 T2-5 B41 A68 T2-4 B41 A69 T2-5 B41 A69 T2-4 B41 A70 T2-5 B41 A70 T2-4 B41 A76 T2-5 B41 A76 T2-4 B41 A77 T2-5 B41 A77 T2-4 B41 A78 T2-5 B41 A78 T2-4 B41 A106 T2-5 B41 A106 T2-4 B41 A11O T2-5 B41 A11O T5-1 B41 A2 T7-1 B41 A2 T5-1 B41 A5 T7-1 B41 A5 T5-1 B41 A35 T7-1 B41 A35 T5-1 B41 A37 T7-1 B41 A37 T5-1 B41 A45 T7-1 B41 A45 T5-1 B41 A46 T7-1 B41 A46

• · ··· * · · ····· ··

122

Table 46

T5-1 B41 A49 T7-1 B41 A49 T5-1 B41 A54 T7-1 B41 A54 T5-1 B41 A66 T7-1 B41 A66 T5-1 B41 A67 T7-1 B41 A67 T5-1 B41 A68 T7-1 B41 A68 T5-1 B41 A69 T7-1 B41 A69 T5-1 B41 A70 T7-1 B41 A70 T5-1 B41 A76 T7-1 B41 A76 T5-1 B41 A77 T7-1 B41 A77 T5-1 B41 A78 T7-1 B41 A78 T5-1 B41 A106 T7-1 B41 A106 T5-1 B41 AllO T7-1 B41 AllO Tl-1 B42 A2 T2-1 B42 A2 Tl-1 B42 A5 T2-1 B42 A5 Tl-1 B42 A35 T2-1 B42 A35 Tl-1 B42 A37 T2-1 B42 A37 Tl-1 B42 A45 T2-1 B42 A45 Tl-1 B42 A46 T2-1 B42 A46 Tl-1 B42 A49 T2-1 B42 A49 Tl-1 B42 A54 T2-1 B42 A54 Tl-1 B42 A66 T2-1 B42 A66 Tl-1 B42 A67 T2-1 B42 A67 Tl-1 B42 A68 T2-1 B42 A68 Tl-1 B42 A69 T2-1 B42 A69 Tl-1 B42 A70 T2-1 B42 A70 Tl-1 B42 A76 T2-1 B42 A76 Tl-1 B42 A77 T2-1 B42 A77 Tl-1 B42 A78 T2-1 B42 A78 Tl-1 B42 A106 T2-1 B42 A106 Tl-1 B42 AllO T2-1 B42 AllO T2-2 B42 A2 T2-3 B42 A2 T2-2 B42 A5 T2-3 B42 A5 T2-2 B42 A35 T2-3 B42 A35 T2-2 B42 A37 T2-3 B42 A37 T2-2 B42 A45 T2-3 B42 A45 T2-2 B42 A46 T2-3 B42 A46 T2-2 B42 A49 T2-3 B42 A49 T2-2 B42 A54 T2-3 B42 A54 T2-2 B42 A66 T2-3 B42 A66 T2-2 B42 A67 T2-3 B42 A67 T2-2 B42 A68 T2-3 B42 A68 T2-2 B42 A69 T2-3 B42 A69

• · · · · · · · · · · · · · · · · · · ·

123

Table 47 φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ

-22-2 Β42 Α70 -2-3 Β42 Α70 -22-2 Β42 Α76 -2-3 Β42 Α76 -22-2 Β42 Α77 -2-3 Β42 Α77 -22-2 Β42 Α78 -2-3 Β42 Α78 -22-2 Β42 Α106 -2-3 Β42 Α106 -22-2 Β42 Α110 -2-3 Β42 Α110 Τ2-4 Β42 Α2 -52-5 Β42 Α2. Τ2-4 Β42 Α5 -52-5 Β42 Α5 Τ2-4 Β42 Α35 -52-5 Β42 Α35 Τ2-4 Β42 Α37 -52-5 Β42 Α37 Τ2-4 Β42 Α45 -52-5 Β42 Α45 Τ2-4 Β42 Α46 -52-5 Β42 Α46 Τ2-4 Β42 Α49 -52-5 Β42 Α49 Τ2-4 Β42 Α54 -52-5 Β42 Α54 Τ2-4 Β42 Α66 -52-5 Β42 Α66 Τ2-4 Β42 Α67 -52-5 Β42 Α67 Τ2-4 Β42 Α68 -52-5 Β42 Α68 Τ2-4 Β42 Α69 -52-5 Β42 Α69 Τ2-4 Β42 Α70 -52-5 Β42 Α70 Τ2-4 Β42 Α76 -52-5 Β42 Α76 Τ2-4 Β42 Α77 -52-5 Β42 Α77 Τ2-4 Β42 Α78 -52-5 Β42 Α78 Τ2-4 Β42 Α106 -52-5 Β42 Α106 Τ2-4 Β42 Α110 -52-5 Β42 Α110 -15-1 Β42 Α2 -17-1 Β42 Α2 -15-1 Β42 Α5 -17-1 Β42 Α5 -15-1 Β42 Α35 -17-1 Β42 Α35 -15-1 Β42 Α37 -17-1 Β42 Α37 -15-1 Β42 Α45 -17-1 Β42 Α45 -15-1 Β42 Α46 -17-1 Β42 Α46 -15-1 Β42 Α49 -17-1 Β42 Α49 -15-1 Β42 Α54 -17-1 Β42 Α54 -15-1 Β42 Α66 -17-1 Β42 Α66 -15-1 Β42 Α67 -17-1 Β42 Α67 -15-1 Β42 Α68 -17-1 Β42 Α68 -15-1 Β42 Α69 -17-1 Β42 Α69 -15-1 Β42 Α70 -17-1 Β42 Α70 -15-1 Β42 Α76 -17-1 Β42 Α76 -15-1 Β42 Α77 -17-1 Β42 Α77 -15-1 Β42 Α78 -17-1 Β42 Α78 -15-1 Β42 Α106 -17-1 Β42 Α106 -15-1 Β42 Α110 -17-1 Β42 Α110

• 9 9 9 9 ···· · · · · · · · · · · · · · · · · · · · · · ·

124

Table 48 9 9 9 9 9 9 9 9 9 9 9 9 99 99

Tl-1 B43 A2 T2-1 B43 A2 Tl-1 B43 A5 T2-1 B43 A5 Tl-1 B43 A35 T2-1 B43 A35 Tl-1 B43 A37 T2-1 B43 A37 Tl-1 B43 A45 T2-1 B43 A45 Tl-1 B43 A46 T2-1 B43 A46 Tl-1 B43 A49 T2-1 B43 A49 Tl-1 B43 A54 T2-1 B43 A54 Tl-1 B43 A66 T2-1 B43 A66 Tl-1 B43 A67 T2-1 B43 A67 Tl-1 B43 A68 T2-1 B43 A68 Tl-1 B43 A69 T2-1 B43 A69 Tl-1 B43 A70 T2-1 B43 A70 Tl-1 B43 A76 T2-1 B43 A76 Tl-1 B43 A77 T2-1 B43 A77 Tl-1 B43 A78 T2-1 B43 A78 Tl-1 B43 A106 T2-1 B43 A106 Tl-1 B43 AllO T2-1 B43 AllO T2-2 B43 A2 T2-3 B43 A2 T2-2 B43 A5 T2-3 B43 A5 T2-2 B43 A35 T2-3 B43 A35 T2-2 B43 A37 T2-3 B43 A37 T2-2 B43 A45 T2-3 B43 A45 T2-2 B43 A46 T2-3 B43 A46 T2-2 B43 A49 T2-3 B43 A49 T2-2 B43 A54 T2-3 B43 A54 T2-2 B43 A66 T2-3 B43 A66 T2-2 B43 A67 T2-3 B43 A67 T2-2 B43 A68 T2-3 B43 A68 T2-2 B43 A69 T2-3 B43 A69 T2-2 B43 A70 T2-3 B43 A70 T2-2 B43 A76 T2-3 B43 A76 T2-2 B43 A77 T2-3 B43 A77 T2-2 B43 A78 T2-3 B43 A78 T2-2 B43 A106 T2-3 B43 A106 T2-2 B43 AllO T2-3 B43 AllO T2-4 B43 A2 T2-5 B43 A2 T2-4 B43 A5 T2-5 B43 A5 T2-4 B43 A35 T2-5 B43 A35 T2-4 B43 A37 T2-5 B43 A37 T2-4 B43 A45 T2-5 B43 A45 T2-4 B43 A46 T2-5 B43 A46

• · • ·

125 r>

Table 49

T2-4 B43 A49 T2-5 B43 A49 T2-4 B43 A54 T2-5 B43 A54 T2-4 B43 A66 T2-5 B43 A66 T2-4 B43 A67 T2-5 B43 A67 T2-4 B43 A68 T2-5 B43 A68 T2-4 B43 A69 T2-5 B43 A69 T2-4 B43 A70 T2-5 B43 A70 T2-4 B43 A76 T2-5 B43 A76 T2-4 B43 A77 T2-5 B43 A77 T2-4 B43 A78 T2-5 B43 A78 T2-4 B43 A106 T2-5 B43 A106 T2-4 B43 AllO T2-5 B43 AllO T5-1 B43 A2 T7-1 B43 A2 T5-1 B43 A5 T7-1 B43 A5 T5-1 B43 A35 T7-1 B43 A35 T5-1 B43 A37 T7-1 B43 A37 T5-1 B43 A45 T7-1 B43 A45 T5-1 B43 A46 T7-1 B43 A46 T5-1 B43 A49 T7-1 B43 A49 T5-1 B43 A54 T7-1 B43 A54 T5-1 B43 A66 T7-1 B43 A66 T5-1 B43 A67 T7-1 B43 A67 T5-1 B43 A68 T7-1 B43 A68 T5-1 B43 A69 T7-1 B43 A69 T5-1 B43 A70 T7-1 B43 A70 T5-1 B43 A76 T7-1 B43 A76 T5-1 B43 A77 T7-1 B43 A77 T5-1 B43 A78 T7-1 B43 A78 T5-1 B43 A106 T7-1 B43 A106 T5-1 B43 AllO T7-1 B43 AllO

126

Moreover preferred are compounds having the above structure, wherein X'-Y 'is one selected from the group OCH ₂ CH = CMe _2, OCH2-2-furyl, OCH ₂ -3-furyl, 0CH ₂ O = Me,

NHCH ₂ CH = CMe ₂ , N (iPr) SO ₂ NHMe, NHCH (Me) CH ₂ OMe, NHiPr, NH-iBu, NHc-Pent,

NHCH ₂ c-Hex, NHc-Hex, NHc-Hex-4 - (= NOMe), NHcHex-4, 4- (OMe) ₂ , NHCH ₂ H ₆ H ₄ -4-

B (OH) ₂ , NHCH ₂ H ₆ H ₄ -2-OH, NHCH ₂ H ₆ H ₃ -3, 4- (OH) 2, NHCH ₂ H ₆ H ₂ -3, 4, 5- (OMe) 3 ,

NHCH ₂ H ₆ H ₄ -4-COOH H ₆ NHC ₂ H ₄ -4-OH, NHCH ₂ -3-hGH ₄ OH, NHCH ₂ -2-furyl, NHCH ₂ -3-furyl, NH-4-tetrahydropyran , NHCH ₂ -benzopyrolyl, NHCH ₂ -2-thiazolyl, NHCH ₂ -quinolyl, NHcHex-4,4-ethylenedioxy, 1-pyrrolidinyl, 4-morpholinyl, 1 piperadinyl, 4thiomorpholinyl, 1-piperidyl.

-N

Even more preferred are compounds wherein -XY 'is OCH ₂ -2-furyl, NHCH ₂ CH = CMe ₂ or OCH ₂ CH = CMe ₂ .

The process for producing Compound I is as follows:

Process for producing compound.

A compound of formula Γ (hereinafter referred to as "compound Γ") can be produced by reacting a compound of formula IIa (hereinafter referred to as "compound IIa") with a bicyclic compound of formula IIIa (hereinafter referred to as "compound IIIa") ) or by reacting a compound of formula IIb (hereinafter referred to as "compound IIb") with a bicyclic compound of formula IIIb (hereinafter referred to as "compound IIIb").

C) - (λ λ-L + Z - (A> - x-γ

W ³ - ^ w ^{2 (} Ia) (lla)

L - (B) - (A _W 2 - / _W tx-γ + c> -z

(Lib) (lib)

Wherein one of L or Z is dihydroxyborane, lower dialkylborane or lower dialkoxyborane and the other is halogen or -OSO2 (C _q F2q ₊ - |) (q is whole number between 0 and 4) and the other symbols are the same as defined above.

Compound I 'can be produced by reacting Compound IIa with Compound IIIa or by reacting Compound IIb with Compound IIIb in a mixture of a suitable solvent such as benzene, toluene, N, N-dimethylformamide, dimethoxyethane, tetrahydrofuran, dioxane, ethanol, methanol or the like; a non-aqueous solution in the presence of a palladium catalyst such as Pd (PPh 3) ₄ , PdCl 2 PPhg ₄ , PdCl 2 (OAc) 2, PdCl 2 CH 2 CN 4 or the like, preferably Pd (PPh 3) ₄ , in basic environment (e.g. NaOEt, Na ₂ CO 3, Et ₄ NCI, Ba (OH) 2, CS 2 CO 3, CsF, NaOH, AgNO 3 or the like) at room temperature or with heating for several tens of minutes to several tens of hours.

One of the substituents of compounds L and Z to be reacted is any of the borane groups useful in the Suzuki reaction (Chemical Communication 1979, 866, Journal of Synthetic Organic Chemistry, Japan, 1993, Vol 51, No. 11, 91) -100) and dihydroxoboran is preferred. The second substituent may be any of the remaining groups that are useful in the Suzuki reaction, for example, halogen, -OSO ₂ (CqF ₂ q + 1), wherein q is an integer ranging from 0 to 4, or the like. Particularly preferred are halogen, trifluoromethanesulfonyloxy (hereinafter referred to as OTf) or the like, and bromine, iodine or OTf are more preferred.

The other substituents on rings A, B and C and -XY of compounds IIa, IIa, IIb and IIIb are some of the groups that do not affect the Suzuki reaction, for example some groups other than halogen and -OSO2 (CqF2q + - |) where q is whole a number between 0 and 4.

For example, Y is an optionally substituted lower alkyl, an optionally substituted lower alkenyl, an optionally substituted lower alkynyl, an optionally substituted acyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted aryl or an optionally substituted five or six membered heterocycle that is fused to the benzene ring; optionally substituted lower alkoxy when X is ΟΗ ₂ - and Y is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl or optionally substituted arylsulfonyl when X is -O- or -NR ¹ -.

• ·

128

Even if any of the substituents on rings A, B and C is halogen, these reactions can be carried out without difficulty when the reactivity of the substituent L with the substituent Z is higher than the reactivity of the halogen with any of the substituents L and Z.

Even if any of the substituents on rings A, B, C and -X-Y is hydroxyl, the above reactions can be advantageously performed. Advantageously, the above reactions may be carried out after protection of the hydroxyl group with a conventional hydroxyl protecting group such as methoxymethyl, benzyl, tert-butyldimethylsilyl, methanesulfonyl, p-toluenesulfonyl or the like, followed by deprotection according to conventional procedures.

As a process for preparing compound Γ, the above Suzuki reaction is most preferred in terms of efficiency and ease of performance, but silicon, zinc, tin or the like may be used in the above scheme instead of borane groups.

For example, in case that one of A and Z is -SiR ⁷ ^ _3-r (Hal) _r wherein ^R17 are independently a lower alkyl, Hal is halogen and r is an integer from 1 to 3 and the other is halogen or OSO2 ( (Qq2q + i), where q is an integer from 0 to 4, the condensation reaction is carried out using a conventional palladium catalyst (Synlett (1991) 845-853, J. Org. Chem. 1996, 61, 7232-7233). Examples of preferred palladium catalysts are (iPr ₃ P) ₂ PdCl ₂ , [(dcpe) PdCl ₂ ] (dcpe = Cy ₂ PCH ₂ CH ₂ PCy ₂ ), (n ³ -C ₃ H ₅ PdCl) 2 and the like.

Even when one of L and Z is -SiR ^ ⁸ , where R ^ ⁸ are independently lower alkyl and the other is halogen, acetyloxy or -OSO2 (CqF2q + <|), where q is an integer from 0 to 4, the target compound can be obtained using a conventional palladium catalyst (preferably Pd (PPh ₃ ) ₄ or the like) (Angew. Chem. Int. Ed. Engl. 25 (1986) 508-524).

When one of L and Z is -Zn (Hal), where Hal is halogen and the other is halogen, the target compound can be obtained (Acc. Chem. Res. 1982, 15, 340-348). Any conventional palladium catalyst can be used and preferred examples include Pd (PPh ₃ ) ₄ , PdCl ₂ (dppf), PdCl ₂ (PPh ₃ ) ₂ , PdCl ₂ (P (o-tolyl) ₃ ) ₂ . Pd (OAc) ₂ or the like.

All of these reactions can be carried out in suitable solvents such as N, N-dimethylformamide, tetrahydrofuran or the like at room temperature or with heating for several tens of minutes to several tens of hours.

129 ·· · 0 · 0 0 · · 0 0 ···· 0 «0 *« 00 • • 0 00 0 0000 0 000000 00 00 00 0 0 0

As compounds IIIa and IIIb in the above reactions, known compounds or compounds derived from a compound of formula Va (hereinafter referred to as "compound Va") or the following formula Vb (hereinafter referred to as "compound Vb") may be used. , which may be manufactured in a known manner or as described below.

(lib) (iVa)

(Hal (IVb) (Vb) wherein D is any group that does not affect the Suzuki reaction of L with Z, and may be the same as L when the compound of formula IVa is a double symmetrical compound. The other symbols are the same as above .

Compound IIb reacts with compound IVa or compound IIa reacts with compound IVb to give compound Va or Vb. When compounds IVa or IVb are not double symmetrical compounds, it is preferred that D is a group that does not affect the Suzuki reaction of L with Z and can easily be converted to L. For example, hydroxyl, formyl, nitro or the like are preferred. In reaction L with Z, as mentioned above, silicon, zinc tin or the like can be used instead of borane groups.

D is converted to the L group which is useful for the Suzuki reaction.

A compound wherein D is hydroxyl may be reacted with a trifluoromethanesulfonating agent such as trifluoromethanesulfonic anhydride, trifluoromethanesulfonyl chloride, N-phenyltrifluoromethanesulfonic acid imide or the like in a suitable solvent such as dichloromethane, chloroform, tetrahydrofuran or benzene in the presence of a base such as sodium hydride , pyridine, triethylamine, potassium carbonate or the like at -20 ° C or with heating for several tens of minutes to several tens of hours to give the target compound wherein L is OTf.

For example, a compound wherein D is hydrogen may be reacted with a halogenating agent such as bromine, chlorine, iodine, N-bromosuccinimide or the like in a suitable solvent such as acetic acid, dichloromethane, chloroform, carbon tetrachloride,

Benzene, water or the like at -20 ° C or with heating for several tens of minutes to several tens of hours to give the target compound wherein L is halogen.

A compound wherein D is formyl can be oxidized using the Baeyer-Villiger reaction to give a compound wherein D is formyloxyl, followed by hydrolysis to yield a compound wherein D is hydroxyl. A compound wherein L is OTf can be obtained in a similar manner as described above.

A compound wherein D is a nitro group can be reduced to give a compound where D is an amino group followed by a Sandmeyer reaction to give a compound where L is halogen.

Process for the preparation of compound I '.

A compound of formula I (hereinafter referred to as "compound I") may be prepared by Suzuki reaction of a compound of formula VI (hereinafter referred to as "compound VI") with a compound of formula IIa (hereinafter referred to as "compound Ha" ") Or by condensation of a compound of formula VII (hereinafter referred to as" compound VII ") with a compound of formula VIIIa (hereinafter referred to as" compound VIIIa ").

(vn) (vmj wherein one of M or Q is hydroxyl or amino and the other is halogen, lower alkylsulfonyloxy, arylsulfonyloxy, lower alkylsulfonyl, arylsulfonyl or methyl having substituents, one of M or Q is lithium or Mg (Hal) wherein Hal is halogen and the other is carboxyl, lower alkoxycarbonyl, carbamoyl or formyl, one of M or Q is formyl and the other is methylhalo, or one of M or Q is ethynyl and the other is halogen, and the other symbols are as defined above .

The conditions for the reaction of Compound VI with Compound IIa are the same as for the preparation of Compound Γ.

131 · · • • i i i i i i i i i • • i • • i • i i • • i i i • i i i • 9 9 9 9 9 9

In the reaction of VII with VIIIa, when V ² in the target compound is -O-, -NH-, -OCH 2 -, -CH 2 O- or -NHCH 2 -, one of M or Q is hydroxyl or amino and the other is the remaining group, such as halogen, lower alkylsulfonyloxy, arylsulfonyloxy, lower alkylsulfonyl, arylsulfonyl or the like or methyl having these groups as substituents. The two compounds are reacted in a suitable solvent such as benzene, toluene, acetone, acetonitrile, Ν, Ν-dimethylformamide, dimethylsulfoxide, pyridine, methanol, ethanol or the like in the presence of a base such as sodium hydride, pyridine, triethylamine, potassium carbonate, sodium hydroxide , potassium hydroxide or the like, if necessary, with the addition of a copper catalyst such as copper powder, CuCl, CuO or the like, at 0 ° C or with heating for a few minutes to several tens of hours to obtain the target compound .

In the reaction of Compound VII with Compound VIIIa, when V ² in the target compound is -CO or -CH (OH) -, one of M or Q is an organism acceptable metal form such as lithium or Mg (Hal), where Hal is halogen, and the other is carboxyl, lower alkoxycarbonyl, carbamoyl or formyl. The two compounds are reacted in a suitable solvent such as diethyl ether, tetrahydrofuran, dimethoxyethane, dioxane or the like at -78 ° C or with heating for a few minutes to several hours to obtain the target compound.

When the target compound is V ² -CH (OR) -, where R is lower alkyl, after obtaining a compound wherein V ² is -CH (OH) -, the obtained compound can be alkylated.

A compound wherein V ² is -CO- can be obtained by reacting a compound wherein V ² is -CH (OH) with an oxidizing agent such as chromic anhydride, Jones reagent or the like in a solvent such as t-butyl alcohol, acetone or the like , depending on the oxidizing agent at 0 ° C or with heating for several hours. A compound wherein V ² is -CH (OH) - can also be obtained by reacting a compound wherein V ² is -CO 3 a reducing agent such as sodium borohydride, aluminum hydride and lithium or the like in a suitable solvent such as diethyl ether, tetrahydrofuran , dimethoxyethane, dioxane, methanol, ethanol or the like.

When a compound wherein V ² of the target compound is -CH = CH-, one of M and Q is formyl and the other is methylhalogen (for example, halogen is chlorine, bromine or iodine). The target compound can be obtained by the Wittig reaction (Organic Reaction, vol. 14, p. 270, 1965).

132 • 0 0 0 0 0 0 0 0 0

0 0 0 0 0 00 ·· • 000 00 · 0 00 00 0 0 0 000 000

0000 00 00 00

When V ² of the target compound is -CH = CH-, one of M and Q is ethynyl and the other is halogen (preferably bromine or iodine). The target compound can be synthesized by a condensation reaction using a commonly used palladium catalyst (e.g., Synthesis, (1980) 627, Tetrahedron, 1982, 38, 631).

Further substituents of rings A, B and C and -XY in compounds VI, IIa, VII and VIIIa can be any substituents that do not affect the Suzuki reaction of L with Z or the condensation reaction of M with Q. Even if in the reaction of VI with All substituents halogens, this reaction can be carried out without difficulty if the reactivity of the substituent L with the substituent Z is higher than the reactivity with the halogen. Even if each of the substituents is hydroxyl, the above reaction may be performed. It is preferred to protect the hydroxyl beforehand and the above reaction is followed by deprotection.

As compound VI in the above scheme, a known compound or a compound of formula X, which is synthesized as follows, may be used.

(VII) (IX) (X) where D 'is a group that does not affect the condensation reaction of M with Q and when the compound of formula IX is a symmetrical compound, D' may be the same group as Q and the other symbols are as defined above.

When the compound of formula (IX) is not a symmetrical compound, it is preferred that D 'is a group that does not affect the condensation reaction M sQ and which can be easily converted to L. For example, hydrogen, formyl, protected hydroxyl, nitro or the like are preferred. Exemplary hydroxyl protecting groups are benzyl, t-butyldimethylsilyl, methoxymethyl and the like. The process for converting D 'to L is similar to the above process for converting D to L. Other various conditions are similar to those used in the reaction of VII with VIIIa.

In the above reaction scheme, a known compound may be used as the compound VIIIa and a compound synthesized in a conventional manner or derived from the above compound Vb may also be used.

In case the compound contains a substituent interfering with the above reaction, the substituent is pre-protected with a suitable protecting group and this protecting group

998 9 9

9

133

9 9999

9, the group is removed in a conventional manner by conventional means. For example, if the hydroxyl interferes with the reaction, it may be protected with methoxymethyl, methanesulfonyl, benzyl, trifluoromethanesulfonyl, tert-butyldimethylsilyl or the like, followed by a suitable deprotection step.

For example, in protecting a hydroxyl by methanesulfonyl, the hydroxyl compound is reacted with methanesulfonyl chloride in a solvent such as dichloromethane, chloroform, carbon tetrachloride or the like in the presence of a base such as triethylamine, pyridine or the like under ice cooling or at room temperature for several hours. The protecting group may be removed with 1-4 N sodium hydroxide, potassium hydroxide, an aqueous solution thereof, sodium methoxide or the like in a solvent such as dimethylsulfoxide, dimethylformamide, tetrahydrofuran, dioxane, dimethoxyethane or the like at room temperature or with heating for several minutes to tens of hours.

When methoxymethyl is used as the hydroxyl protecting group, the hydroxyl-containing compound can be reacted with chloromethyl methyl ether in a solvent such as tetrahydrofuran, dioxane, dimethoxyethane or the like in the presence of sodium hydride, diisopropylethylamine or the like to form a hydroxyl-protected compound. The compound may be subjected to a conventional deprotection reaction using hydrochloric acid, sulfuric acid or the like in a solvent such as methanol, tetrahydrofuran, acetic acid or the like.

When tert-butyldimethylsilyl is used as a protecting group, the hydroxyl-containing compound can be reacted with tert-butyldimethylsilyl chloride, tert-butyldimethylsilyl triflate or the like in a solvent such as dimethylformamide, acetonitrile, tetrahydrofuran, dimethylformamide, dichloromethane or the like in the presence of imidazole, triethylamine , 2,6-lutidine or the like. In the deprotection reaction, the protected compound may be reacted with tetrabutylammonium fluoride or the like in a solvent such as tetrahydrofuran or the like.

Thus, the obtained compound of the present invention can be converted to its precursor. The term prodrug includes compounds that can be readily converted to a compound that has activity in the living body of the present invention. For example, a hydroxyl group or an amino group that is attached at any possible position in a compound of the present invention may be substituted with a conventional group in the manufacture of the precursor. For example

134

99 99 9999 99 99 • 99 * 99 99 999 * • 99 99 9 9999

999 99 99 9 9 99 9 • 9 999 9999 99 99 99 99 9 99 99 substituted acyl (wherein the substituent is carboxyl, sulfo, amino, lower alkylamine or the like), phosphonoxyl or the like can be introduced in place of hydroxyl and substituted alkoxycarbonyl (where the substituent is halogen, acyloxy, hydroxyacyloxy, carboxyacyloxy, heterocyclylcarbonyloxy or the like) or substituted alkyl (wherein the substituent is aroylamine, which may be substituted with lower alkoxy acyloxy or the like) may be introduced into the amino group.

More specifically, when ring A or C has hydroxyl as a substituent, substituents such as -COCH ₂ CH ₂ COOH, -COCH = CHCOOH, -COCH ₂ SO ₃ H, PO ₃ H ₂ , -COCH ₂ NMe ₂ , -CO can be introduced. -Py where Py is pyridine or the like. When ring A or C has an amino group as a substituent (e.g. X, X 'or the like), substituents such as -COOCH ₂ O (C = O) CH ₂ OH, -COOCH ₂ O (C = O) CH ₂ , may be introduced. CH ₂ COOH, COOCH ₂ OAc, -COOCH (Me) OAc, -COOCH (Me) OCOCMe ₃ ,

COOCH ₂ OCO (CH ₂ ) ₁₄ Me, -COOCH ₂ OCO-Pyr, -CH ₂ NHCO-C ₆ H ₄ -o-OCH ₂ OAc or the like.

The immunosuppressive or antiallergic agent of the present invention is useful for the prevention or treatment of allergic diseases such as an organ or tissue rejection symptom, graft versus host disease caused by bone marrow transplantation, atopic allergic diseases (e.g., bronchial asthma, allergic rhinitis) , allergic dermatitis and the like), hypereosinophilic syndrome, allergic conjunctivitis, systemic lupus erythematosus, polymyositis, dermatomyositis, inflammation of the sclera, MCTD, chronic rheumatoid arthritis, bowel inflammation, hay fever, allergic rhinitis, urticaria, psoriasis.

The compound of the invention may be administered orally or parenterally as an immunosuppressor or antiallergic agent or as an IgE suppressant. For oral administration, it may be in any conventional form such as tablets, granules, powders, capsules, pills, solutions, syrups, mucosal tablets, sublingual tablets and the like. When the compound is administered parenterally, any conventional form is preferred, for example, injections (e.g., intravenous, intramuscular), suppositories, skin preparations, vapors and the like. Oral administration is particularly preferred.

A pharmaceutical composition can be made by mixing an effective amount of a compound of the present invention with various pharmaceutical ingredients.

9 4

9 4

4 4

4 ···

94 • · · 4 4

9 4

4 4

135 suitable for the mode of administration, such as carriers, binders, humectants, disintegrants, lubricants, diluents and the like. When the composition will be injected, the active ingredient should be sterilized with a suitable carrier to form a pharmaceutical composition.

Examples of carriers are lactose, sucrose, glucose, starch, calcium carbonate, crystalline cellulose and the like, examples of binders include methylcellulose, carboxymethylcellulose, hydroxypropylcellulose, gelatin, polyvinylpyrrolidone and the like, examples of disintegrants are carboxymethylcellulose, sodium carboxymethylcellulose, starch, alginate sodium lauryl sulfate and the like, examples of lubricants are talc, magnesium stearate, macrogol and the like. Cocoa oil, macrogol, methylcellulose and the like can be used as basic suppository materials. When the formulation is made in the form of a solution, emulsified injection or suspension injection, dissolution enhancers, suspending aids, emulsifiers, stabilizers, preservatives, isotonic agents and the like can be added. For oral administration, sweetening, flavoring and the like may be added.

Although the dosage of the composition of the invention, such as an immunosuppressor or antiallergic or anti-IgE suppressant, should be determined taking into account the patient's age and body weight, type and degree of disease, route of administration or the like, conventional dosage for oral administration to an adult human is 0.05 to 100 mg / kg / day and 0.1 to 10 mg / kg / day is preferred. For parenteral administration, although the dose varies greatly according to the route of administration, the usual dose is 0.005 to 10 mg / kg / day, preferably 0.01 to 1 mg / kg / day. The dose may be administered in one or more portions per day.

The present invention is further illustrated by the following examples and experiments, which are not intended to limit the scope of the present invention.

DETAILED DESCRIPTION OF THE INVENTION

The abbreviations used in the examples mean the following.

Ac acetyl Bn benzyl Et ethyl iPr isopropyl

136 99 9 9 9 9 9 9 9 9 9

9 9 9 9

999 99 99 99 99

9 9 9 9 9

999 98 99 9 9 9 9 9

Me methyl Ms methanesulfonyl Ph phenyl Py pyridyl TBS tertiary butyldimethylsilyl TFAA trifluoroacetic anhydride THF tetrahydrofuran Example 1: Synthesis of compounds Ia-71, Ia-73, Ia '

(B) ₂ B

OBn

Me

Br

in / - * (Π OTBS

TBSO 2 - / - B (OH) ₂ <3 |

Pd (Ph ₃ P) ₄ 2M Na ₂ CO ₃ -toluene

Pd (Ph ₃ P) ₄ 2M Na ₂ CO ₃ -toluene

(Step 1) Synthesis of compound 2.

To a solution of 831 mg (2.32 mmol) of compound 1 (WO98 / 04508), reference 1) in 12 mL of toluene was added 701 mg (2.79 mmol) of 2,5-dibromo-3-methylpyridine, 80 mg (0, 07 mmol) tetrakis (triphenylphosphine) palladium (0) and 6 ml aqueous 2 M sodium carbonate solution

137 • fcfc ·· fcfcfcfc fcfc fcfc • fcfcfc fcfc fc fcfcfcfc • fcfc fcfc · fcfcfcfc • fcfcfc fcfc fcfc fcfc fcfc · · fcfcfc · · · fcfcfc · · · fcfcfc The mixture was refluxed under nitrogen for 4 hours. After cooling, the mixture was diluted with water and extracted with ethyl acetate. The extract was washed with saturated brine, dried and concentrated. The residue was purified by silica gel chromatography (hexane-ethyl 97: 3) to give compound 2 (808 mg; 60% yield).

(Step 2) Synthesis of compound 4.

Following the procedure described in Step 1, 408 mg (0.83 mmol) of Compound 2 was treated with 231 mg (0.92 mmol) of boronic acid (3) (GB 2276162 A) to give Compound 4 (411 mg; 81% yield). .

(Step 3) Synthesis of compound Ia-71.

To a solution of compound 4 (411 mg, 0.67 mmol) in tetrahydrofuran (3.4 mL) was added a solution of 1 M tetrabutylammonium fluoride in tetrahydrofuran (1.4 mL, 1.4 mmol) and the mixture was stirred for 3 hours. The solution was poured into a 5% aqueous solution of acidic potassium sulfate and extracted with ethyl acetate. The extract was washed with saturated brine, dried and concentrated. The residue was crystallized from ethyl acetate to give compound Ia-71 (247 mg; 96% yield).

(Step 4) Synthesis of compound Ia-75.

To a solution of 227 mg (0.59 mmol) of 1a-75 in 3 mL of tetrahydrofuran was added sequentially 0.17 mL (1.18 mmol) of triethylamine and 0.07 mL (0.89 mmol) of methanesulfonyl chloride, and the mixture was stirred for 20 hours at room temperature. The solution was diluted with ethyl acetate, washed successively with water, 5% sodium bicarbonate solution and saturated brine, dried and concentrated. The residue was crystallized from hexane-ethyl acetate to give compound 1a-75 (303 mg; 95% yield).

(Step 5) Synthesis of compound 5.

To a solution of 283 mg (0.52 mmol) of I-75 in 2.6 mL of dichloromethane was added a solution of 1 M borontribromide in 0.63 mL (0.63 mmol) of dichloromethane at -78 ° C and the mixture was at the same temperature stirred for 1 hour. After the excess reagent was quenched by the addition of methanol, the solution was poured into 5% aqueous sodium bicarbonate and extracted with ethyl acetate. The extract was washed with saturated brine, dried and concentrated. The residue was crystallized from ethyl acetate / hexane to give compound 5 (204 mg; 87% yield).

(Step 6) Synthesis of compound Ia-76.

138 · · · φφ φφφ · · · · · · · · · · · · · · · e · e · e · · · · · · · · · · · · · · · · · · · ·

Κ to a solution of 184 mg (0.41 mmol) of compound 5 in 2 ml of acetone, 169 mg (1.23 mmol) of potassium carbonate and 0.12 ml (1.02 mmol) of prenyl bromide were added sequentially and the mixture was stirred for 14 hours at room temperature. The solution was diluted with ethyl acetate, washed successively with water and saturated brine, dried and concentrated. The residue was purified by silica gel chromatography (hexane-ethyl 1: 1) and crystallized from hexane-ethyl acetate to give compound 1a-76 (170 mg; 80% yield).

(Step 7) Synthesis of compound Ia-73.

To a solution of 149 mg (0.29 mmol) of Ia-76 in 1.4 mL of tetrahydrofuran was added a 28% solution of sodium methoxide in 0.6 mL (2.89 mmol) of methanol under ice-cooling, and the mixture was stirred for 17 hours at room temperature. The solution was poured into 5% aqueous ammonium chloride solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried and concentrated. After purification of the residue by silica gel chromatography (hexane-ethyl 7: 3), the obtained product was crystallized from diethyl ether-hexane to give compound 1a-73 (88 mg; 84% yield).

Example 2: Synthesis of compounds 1b-15, 1b-37 and 1b-49

Vj / ^N \

Me (6)

Fe, NH ₄ Cl

Ms ₂ O, Py

CH ₂ Cl ₂

Pd (Ph ₃ P) ₄ 2M Na ₂ CO ₃ -toluene

toluene, H ₂ O

(Step 1) Synthesis of compound 1b-49.

Following the procedure described in Example 1, Step 1, 200 mg (0.74 mmol) of boronic acid was treated with 236 mg (1.49 mmol) of 2-chloro-5-nitropyridine to give 1b-49 (232 mg; 90% yield). .

(Step 2) Synthesis of compound 1b-15.

139 • 99 99 9

9999 98 9 9999

999 99 99 99 99

9,999,999

99 99 99 99 99

To a solution of 257 mg (0.74 mmol) of 1b-49 in 5 mL of toluene was added 5 mL of water, 207 mg (3.70 mmol) of iron powder and 213 mg (3.70 mmol) of ammonium chloride, and the mixture was stirred and heated at reflux for 15 hours. After cooling, the insoluble material was removed by filtration on celite. The filtrate was extracted with ethyl acetate and the extract was washed with saturated brine, dried and concentrated. After purification of the residue by silica gel chromatography (hexane-ethyl 1: 3), the obtained product was crystallized from ethyl acetate to obtain compound Ib15 (161 mg; 69% yield).

(Step 3) Synthesis of compound 1b-37.

To a solution of 130 mg (0.41 mmol) of Ia-15 in 4 mL of dichloromethane was added 0.05 mL (0.61 mmol) of pyridine and 86 mg (0.49 mmol) of methanesulfonic anhydride under ice-cooling, and the mixture was stirred for 1 hour. The solution was diluted with ethyl acetate, washed sequentially with water, 5% aqueous sodium bicarbonate solution and saturated brine, dried and concentrated. The residue was crystallized from ethyl acetate to give compound 1b-37 (124 mg; 77% yield).

Example 3: Synthesis of compounds 1b-11, 1b-12, 1b-16, 1b-21, 1b-46 and 1b-47

1) cis - 1/ _2- N-

TFAA

1) 20% Pd (OH) ₂ / CH ₂ , MeOH-dioxane

About me

CH ₂ Cl ₂

2)

Br

F ₃ COC

OMs

THF

OH

140 ti ti ti ti ti ti ti ti ti ti ti ti ti ti (Step 1) Synthesis of compound 1b-46.

To a mixture of solutions of 867 mg (1.36 mmol) of compound 7 (WO98 / 04508), refs. 4 and 6) in 16 mL of 1,2-dimethoxyethane and 5 mL of ethanol was added 200 mg (1.26 mmol) of 2-chloro-5- nitropyridine, 44 mg (0.04 mmol) of tetrakis (triphenylphosphine) palladium (0) and 5 mL of aqueous 2 M sodium carbonate solution at room temperature and the solution was refluxed under nitrogen for 3 hours. After cooling, the mixture was diluted with water and extracted with ethyl acetate. The extract was washed with saturated brine, dried, concentrated, and the obtained residue was dissolved in 6 mL of tetrahydrofuran. A solution of 1 M tetrabutylammonium fluoride in 2 mL (2.02 mmol) of tetrahydrofuran was added to the solution under ice-cooling, and the mixture was stirred for 1.5 hours. Then the solution was poured into water and extracted with ethyl acetate, the extract was washed with saturated brine, dried and concentrated. The residue was purified by silica gel chromatography (hexane-ethyl acetate 7: 3), crystallized from ethyl hexane / ethyl acetate to give compound 1b-46 (472 mg; 79% yield).

(Step 2) Synthesis of compound 1b-47.

Following the procedure of Example 1, Step 4, a solution of 458 mg (0.97 mmol) of 1b-46 in 4.8 mL of tetrahydrofuran was treated with 0.40 mL (2.89 mmol) of triethylamine and 0.19 mL ( 2.41 mmol) of methylsulfonyl chloride gave 1b-47 (572 mg; 94% yield).

(Step 3) Synthesis of compound 1b-12.

Following the procedure of Example 2, Step 2, 547 mg (0.87 mmol) of 1b-47 was treated with 242 mg (4.34 mmol) of iron powder and 232 mg (4.34 mmol) of ammonium chloride to give 1b-12 (461 mg; 89% yield).

(Step 4) Synthesis of compound 1b-21.

To a solution of 110 mg (0.18 mmol) of 1b-12 in 1.8 mL of dichloromethane was added 0.03 mL (0.22 mmol) of trifluoroacetic anhydride under ice-cooling, and the mixture was stirred at room temperature for 2 hours. The solution was diluted with ethyl acetate, washed successively with water, 5% aqueous sodium bicarbonate solution and saturated brine, dried and concentrated. The residue was crystallized from diethyl ether-hexane to give compound 1b-21 (122 mg; 96% yield).

(Step 5) Synthesis of compound 1b-11.

141

A mixture of 122 mg (0.18 mmol) of 1b-21.24 mg of a 20% mixture of palladium hydroxide and 1.8 ml of methanol and 1.8 ml of 1,4-dioxane was stirred under nitrogen for 15 hours at room temperature. After insoluble material was filtered off through celite, the filtrate was concentrated to give 110 mg of residue.

To a solution of the remaining material in 3.5 mL of Ν, Ν-dimethylformamide was added 73 mg (0.53 mmol) of potassium carbonate and 0.05 mL (0.39 mmol) of prenyl bromide respectively, and the mixture was stirred for 4 hours. The solution was diluted with ethyl acetate, washed successively with water, saturated brine, dried and concentrated. The residue was purified by silica gel chromatography (hexane-ethyl acetate 7: 3), crystallized from diethyl ether-hexane to give compound 1b-11 (121 mg; 93% yield).

(Step 6) Synthesis of compound 1b-16.

Following the procedure of Example 1, Step 7, Compound 1b-16 was obtained (72 mg; 99% yield) from 111 mg (0.15 mmol) of Compound 1b-111.

14: Synthesis of compounds 1c-23 and 1c-24

1) Bu ₄ NF. THF (2) MsCl, Et ₃ N, THF (9) ^OTBS

Me,, OMs (ni

2) hydroquinone K ₂ CO ₃

Me OMs

THF

NaOMe, MeOH

(Step 1) Synthesis of Compound 9.

Following the procedure of Example 1, in step 1, 500 mg (2.35 mmol) of the compound was reacted with 883 mg (2.46 mmol) of boronic acid (1) to give compound 9 (983 mg; 94% yield).

142

• 9 · 9 « ·· »· 9 · • 9 * 9 99 • l «· • • 9 9 • 49 « • 9 9 4 9 9 • 9 • • · • • 9 9 9 4 9 »·· ·· • 9 4 9 « 49

(Step 2) Synthesis of compound 10.

To a solution of 983 mg (2.20 mmol) of compound 9 in 10 mL of tetrahydrofuran was added 1 M tetrabutylammonium fluoride in 2.2 mL (2.20 mmol) of tetrahydrofuran under ice-cooling, and the mixture was stirred at room temperature for one hour. The solution was poured into water, extracted with ethyl acetate, washed with saturated brine, dried and concentrated. The residue was dissolved in 10 mL of tetrahydrofuran, then 0.46 mL (3.29 mL) of triethylamine and 0.20 mL (2.64 mmol) of methanesulfonyl chloride were gradually added under ice-cooling, and the mixture was stirred at the same temperature for 30 minutes. The solution was diluted with ethyl acetate, washed successively with water, 5% aqueous sodium bicarbonate solution and saturated brine, dried and concentrated. The residue was purified by silica gel chromatography (hexane-ethyl acetate 7: 3) to give compound 10 (881 mg; 98% yield).

(Step 3) Synthesis of compound 11.

A solution of 120 mg (0.29 mmol) of 10 and 11 mg of a 10% mixture of palladium hydroxide and 2 ml of methanol and 2 ml of 1,4-dioxane was stirred under nitrogen for 2 hours at room temperature. Insoluble material was filtered off through celite and the filtrate was concentrated. To a solution of the remaining material in 3 mL of methanol was added 11 mg (0.29 mmol) of sodium borohydride and the mixture was stirred for 30 minutes. The solution was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, dried and concentrated. To a solution of the crude product thus obtained in 3 ml of acetone was added sequentially 122 mg (0.88 mmol) of potassium carbonate and 0.10 ml (0.88 mmol) of prenyl bromide, and the mixture was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate and washed sequentially with water and saturated brine, dried and concentrated. The residue was purified by silica gel chromatography (hexane-ethyl acetate 7: 3) to give compound 11 (108 mg; 96% yield).

(Step 4) Synthesis of compound 1c-24.

To a solution of 108 mg (0.28 mmol) of 11 in 2 mL acetonitrile was added 87 mg (0.33 mmol) of carbon tetrabromide under ice-cooling, and the mixture was stirred at room temperature for 1 hour. 152 mg (1.38 mmol) of hydroquinone and 114 mg (0.83 mmol) of potassium carbonate were added to the mixture, and they were stirred at room temperature for 20 hours. The mixture was poured into dilute hydrochloric acid and extracted with ethyl acetate. The extract was washed with 5% aqueous sodium bicarbonate solution, saturated brine, dried and concentrated. The remainder was cleaned · φ φ φ · · φ φ φ φ * · · · · · · · φ φ φ

9 «• Φ

143 chromatography on silica gel (hexane-ethyl acetate 7: 3) gave Compound Ic24 (61 mg; 46% yield).

(Step 5) Synthesis of compound 1c-23.

Following the procedure of Example 1, Step 7, Compound 1c-23 was obtained (34 mg; 69% yield) from 59 mg (0.12 mmol) of Compound 1c-24.

Example 5: Synthesis of compounds 1b-539 and 1b-540

(Step 1) Synthesis of compound 1b-539

Compound 1b-250 (444 mg, 1 mmol) was dissolved in anhydrous ether (40 mL) under ice-cooling. Chloromethyl chloroformate (194 mg, 1 mmol) and triethylamine (210 mg, 1 mmol) were added successively to the solution under a nitrogen atmosphere, and the mixture was stirred for 4 hours without ice cooling. The precipitate in the reaction mixture was filtered off and the filtrate was washed with water, dried over sodium sulfate anhydride, concentrated under reduced pressure to obtain 540 mg of 1b-539 as an oil.

Elemental analysis for C 31 H 34 N 2 O 3 FCI

Calcd. C, 69.33; H, 6.38; N, 5.22; F, 3.54; Cl, 6.60.

Analyzed: C, 68.85; H, 6.42; N, 5.21; F, 3.58; Cl, 7.06.

(Step 2) Synthesis of 1b-540

A mixture of glycolic acid (38 mg, 0.5 mmol), potassium carbonate (35 mg, 0.25 mmol) and N, N-dimethylformamide (1 mL) was stirred under reduced pressure for 10 minutes at room temperature. A solution of compound 1 (54 mg, 0.1 mmol) in N, N-dimethylformamide (0.5 mL) and potassium bromide (12 mg, 0.1 mmol) was added and the mixture was stirred vigorously under argon for 20 hours. The mixture was diluted with ether (5 mL) and the insoluble material was filtered off. The filtrate was washed with water, dried over sodium sulfate anhydride and concentrated under reduced pressure. Remaining coarse • «• ····· · · · · · · · ····· · · ·

The 144 product was purified by silica gel chromatography (eluent: hexane-ethyl acetate (2: 1)) to give 27 mg of 1b-540 as an oil.

Elemental analysis for C 33 H 37 N 2 O 6 F

Calcd. C, 68.73; H, 6.47; N, 4.86; F, 3.29.

Analyzed: C, 68.59; H, 6.68; N, 4.98; F, 3.25.

Example 6: Synthesis of 1b-541

A mixture of succinic acid (590 mg, 5 mmol), potassium carbonate (345 mg, 2.5 mmol) and N, N-dimethylformamide (6 mL) was stirred under reduced pressure for 10 minutes at room temperature. Solutions of compound 1b-539 (537 mg, 1 mmol) in N, N-dimethylformamide (5 mL), obtained as described in Example 5, Step 1, and sodium iodide (70 mg, 0.5 mmol) were added sequentially, and the mixture was stirred at room temperature. vigorously stirred under argon for 5 days. The mixture was poured into aqueous 5% acetic acid and extracted with ether-hexane (4: 1). After the obtained mixture was dried over sodium sulfate anhydride, the solvent was removed. The remaining crude product was purified by silica gel chromatography (eluent: chloroform-methanol (20: 1)) to obtain 60 mg of 1b-541 as an oil.

Elemental analysis for C 35 H 39 N 2 O 7 F

Calcd: C, 67.95; H, 6.35; N, 4.53; F, 3.07.

Analyzed: C, 68.25; H, 5.96; N, 4.64; F, 3.13.

LSIMS; m / z = 618 [M + M] &lt; + &gt;.

Example 7: Synthesis of Other Compounds I

The following compounds I were synthesized by an analogous procedure. The structures and physical constants are shown below. Tables 50 to 55 represent the partial structures used as abbreviations in Table 56 or others, A1, A2, ... B1, B2, ... C1, C2 ....

• · · · · · · · · ·

• · ·

145

Table 50

R ⁴ , R ⁴

W ^Y

-x — γ

R ⁴ R5 R6 R ⁷ X Y Al H II H H 0 H A2 II H H H 0 CH _of -2-furyl A3 H H II H 0 CIUCsHs A4 H II II II 0 CH ₂ C ₆ H ₄ -4-Me A5 II H H H 0 CH ₂ CH = CMe ₂ A6 OH H II H 0 Cl I ₂ Cell A7 OAc H H H 0 CIHCeHs A8 OMs H 11 II 0 CH ₂ C ₆ Il5 A9 OSOzCFg II II H 0 ClkCeHs A10 OSO ₂ Ph H H H 0 CIHCeHs All About me II H II 0 CH ₂ C ₆ H ₅ A12 OII II H H 0 CH ₂ C ₆ H ₄ -2-Me A13 OH H H II 0 CH ₂ C ₆ H4-3 Me A14 OH . H II H 0 _CH2-Me CsH4-4 A15 OMs H II H 0 CH ₂ CeH ₄ -2-Me A16 OMs H II H 0 CH ₂ C ₆ H4-3 Me A17 OMs II II H 0 CH ₂ C ₆ H4-4 Me A18 OH H H H 0 CH ₂ C ₆ H 4-2-OMe A19 OH H II H 0 CH ₂ C ₆ H4-3-OMe A20 OH II H H 0 CH ₂ C ₆ H4-4-OMe A21 OMs H H H 0 CH ₂ C ₆ H ₄ -2-OMe A22 OMs H H H 0 _CH2 OMe CeH4-3 A23 OMs H H H 0 _CH2 OMe CeH4-4 A24 OH H II H 0 CH ₂ -2-Py A25 OH H II H 0 CH _of -3-Py A26 OH H II H 0 CH ₂ -4-Py A27 OMs II II H 0 CH ₂ -2-Py A28 OMs II H II 0 CH ₂ -3-Py A29 OMs 11 II H 0 CH ₂ -4-Py A30 OH H H II 0 CH ₂ CH ₂ C ₆ H ₅ A31 OMs H H H 0 cii ₂ ch ₂ c ₆ h ₅ A32 OH H H H 0 CH ₂ CH = CMe ₂ A33 OMs H H H 0 CH ₂ CH = CMe ₂ A34 OH H H H 0 CH ₂ CH = CC _{1 2} A35 About me II H H 0 CH ₂ CH = CMe ₂

• · · · · ·

146

Table 51

R4 R5 R ^s R ⁷ X Y A36 About me H H H 0 CH ₂ CH = CC _{1 2} A37 F H H H 0 CH ₂ CH = CMe ₂ A38 F H H H 0 CH ₂ CH = CC _{1 2} A39 OH H H H 0 CH ₂ CH ₂ CH = CMe ₂ A40 OMs H H H 0 CH ₂ CH ₂ CH = CMe ₂ A41 H H H H NMe Me A42 H H H H NH H A43 H H H H NH Me A44 H H H H NH iPr A45 H H H H NH ch ₂ ch = ch ₂ A46 H H H H NH CH ₂ CH = CMe ₂ A47 H H H H NH CH ₂ C = CH A48 H H H H NH c-Hex A49 H H H H NH _CH2-c-Hex A50 H H H H NH ch ₂ c ₆ h ₅ A51 H H H H NH CH ₂ C ₄ H ₄ -4 · COOMe A52 H H H H NH CH ₂ C ₈ H ₄ -4-COOH A53 H H H H NH CH ₂ -4-Pyr A54 H H H H NH CH ₂ -2-furyl A55 H H H H NH CH ₂ -3-furyl A56 H H H H NH CH ₂ -2-thienyl A57 H H H H NH CH ₂ -3-thienyl A58 H H H H NCH ₂ CH = CMe ₂ SO ₂ NHMe A59 H H H H NMe Sat ₂ nh ₂ A60 About me H H H NH CH ₂ CH = CMe ₂ A61 About me H H H NH ch ₂ c ₆ h ₅ A62 Me H H H NH CH ₂ CH = CMe ₂ A63 Me H H H NH ch ₂ c ₆ h ₅ A64 H F H H NH H A65 H F H H NH iPr A66 H F H H NH iBu A67 H F H H NH CH ₂ CH = CMe ₂ A68 H F H H NH cPent A69 H F H H NH cHex A70 H F H H NH CH ₂ cHex A71 H F H H NH CH ₂ C ₈ H ₄ -4-Et A72 H F H H NH CH ₂ C ₄ H ₄ -4-iPr A73 H F H H NH CH ₂ C ₈ H ₄ -4-COOH A74 H F H H NH CH ₂ C ₈ H ₄ -4-COOMe A75 H F H H N-iPr SO ₂ NH ₂ A76 H F H H N-iPr SO ₂ NHMe A77 H F H H NCH ₂ CH = CMe ₂ SO ₂ NHMe

• · · ·

147

Table 52

R4 R5 R * 5 R ⁷ X Y A78 F H H H NH CH ₂ CH = CMe ₂ A79 F H H H NH CH ₂ C ₆ H ₅ A80 H Cl H H NH H A81 H Cl H H NH CH ₂ CH = CMe ₂ A82 H Cl H H NH cHex A83 H Cl H H NH CH ₂ cHex A84 Cl H H H NH CH ₂ CH = CMe ₂ A85 Cl H H H NH ch ₂ c ₆ h ₅ A86 H H H H NH 4-tetrahydropyran A87 H H H H NH C ₆ H ₄ -4-B (OH) ₂ A88 H H H H NH CH ₂ C ₆ H ₄ -2-OMe A89 H H H H NH CH ₂ C ₈ H ₂ -3,4,5- (OMe) 3 A90 H H H H NH CH (Me) CH ₂ OMe A91 H H H H NH CH ₂ cHex-4,4- (OMe) ₂ A92 H H H H NH CH ₂ C ₈ H ₈ -3,4- (OH) ₂ A93 H H H H NH CH ₂ C ₆ H ₄ -4-OH A94 H H H H NH A95 H H H H NH CH ₂ C ₈ H ₄ -3-OH A96 H H H H N-pyrroryl A97 H H H H NH CH ₂ -2-thienyl A98 H H H H NH cHex-4 (= NOMe) A99 H H H H NH CH ₂ -2-thiazole A100 H H H H NH ^-H 2 C in Q H A1O1 H H H H NH CH ₂ C ₈ H ₄ -4-OMe A102 H H H H NH ^{_ h} = ^ch G ⁿ v? A103 H H H H 0 CH ₂ C = CMe A104 H Me H H NH CH ₂ CH = CMe ₂ A1O5 H Me H H NH CH ₂ C ₆ H ₅ A106 H F H H NH ch ₂ c ₆ h ₅ A1O7 F H H H 0 H A108 F H H H 0 Me A109 F H H H 0 CH ₂ -2-furyl AllO F H H H 0 CH ₂ C ₈ H ₅ Alll H H H H Me Me A112 H H H H WITH CH ₂ CH = CMe ₂ A113 H H H H Sat ₂ nh ₂ A114 H F H H Sat ₂ nh ₂

148

Table 53 β ·

R5 R6 R ⁷ X Y Α115 H H H H NH o ^ ^Me Al 16 H H H H NH CH ₂ C (Me) = CHMe A117 H H H H NH CH ₂ C = CMe A118 H H H H NCH ₂ CH = CMe ₂ CH ₂ CH = CMe ₂ A119 H F H H NCOOCH ₂ C1 CH ₂ CH = CMe ₂ A120 H F H H NCOOCH ₂ OCOCH ₂ OH CH ₂ CH = CMe ₂ A121 H F H H NCOOCH ₂ OCOCH ₂ CH ₂ COOH CH ₂ CH = CMe ₂ A122 H F H H NCOOCH ₂ OCOMe CH ₂ CH = CMe ₂ A123 H F H H NCOOCH (Me) OCOMe CH ₂ CH = CMe ₂ A124 H F H H NCOOCH (Me) OCOCMe ₃ CH ₂ CH = CMe ₂ A125 H F H H NCOOCH2OCO (CH _{2) 14} Me CH ₂ CH = CMe ₂ A126 H F H H NCOOCH ₂ OCO-3-Pyr CH ₂ CH = CMe ₂ A127 H F H H NCH ₂ NHCO-C ₆ H ₄ -OCH ₂ OCOMe CH ₂ CH = CMe ₂ A128 H H H H NCOOCH ₂ OCOCH ₂ OH CH ₂ CH = CMe ₂ A129 H H H H NCOOCH ₂ OCOMe CH ₂ CH = CMe ₂ A130 H H H H NCOOCH (Me) OCOCMe ₃ CH ₂ CH = CMe ₂ A131 H H H H NCOOCH ₂ OCO-3-Pyr CH ₂ CH = CMe ₂ A132 F H H H NCOOCH ₂ OCO ch ₂ ch ₂ cooh CH ₂ CH = CMe ₂ A133 F H H H NCOOCH (Me) OCOMe CH ₂ CH = CMe ₂ A134 F H H H NCOOCH ₂ OCO (CH ₂ ) ₁₄ Me CH ₂ CH = CMe ₂ A135 F H H H NCH ₂ NHCO-C ₆ H ₄ -OCH ₂ OCOMe CH ₂ CH = CMe ₂ A136 H F H H NCOOCH ₂ OCOCH ₂ OH cPent A137 H F H H NCOOCH ₂ OCOMe cPent A138 H F H H NCOOCH (Me) OCOCMe ₃ cPent A139 H F H H NCOOCH ₂ OCO-3-Pyr cPent A140 H Cl H H NCOOCH ₂ OCO ch ₂ ch ₂ cooh CH ₂ CH = CMe ₂ A141 H Cl H H NCOOCH (Me) OCOMe CH ₂ CH = CMe ₂ A142 H Cl H H NCOOCH2OCO (CH _{2) 14} Me CH ₂ CH = CMe ₂ A143 H Cl H H NCH ₂ NHCO-C ₆ H ₄ -OCH ₂ OCOMe CH ₂ CH = CMe ₂

149

Table 54 Table 54 Table 54

R ⁹ R ⁸

R ⁸ R ⁹ Rio Ru BI About me H H About me B2 About me H OH About me B3 About me H OMs About me B4 Me H H Me B5 Me H OH Me B6 Me H OMs Me B7 Me Me Me Me B8 Me Me About me Me B9 Me Me OH Me BIO Me Me Me About me Bil Me Me Me OH B12 About me Me Me About me B13 Me H Me Me B14 Me Me H Me B15 Me H F Me B16 Me F H Me B17 About me H H Me B18 Me H H About me B19 Cl H H Cl B20 OEt H H OEt B21 OiPr H H OiPr B22 OcPr H H OcPr B23 About me Me Me COOMe B24 Me Me Me COOMe B25 SMe H H SMe B26 SEt H H SEt B27 COOMe Me Me About me B28 Me Me Me Cl B29 Me About me H Me B3O COOMe Me Me Me B31 Cl Me Me Me B32 H Me Me Cl B33 Me H Cl Me B34 H Me Cl H B35 Me H H Cl B36 Me Me H H B37 H Me H Me B38 Me H Me H B39 About me About me H H B40 H About me H About me B41 About me H About me H B42 H Me H About me B43 About me H Me H

150

Table 55 • «9 99 9999 99

9999 99 9 · · ♦

9999 99 9 99 99

9 · · 999

99999 99 · 9999

R ¹³ R ¹²

q15 q14

R ¹² R ¹³ R> " R> ⁵ -X’-Y ' Cl H H H H H C2 H H H H OH C3 H H H H OMs C4 H H H H About me C5 H H H H nh ₂ C6 H H H H NMe ₂ C7 H H H H SMe C8 H H H H Ms C9 H H H H F CIO H cf ₃ H H H Target H no ₂ H H H C12 H nh ₂ H H H C13 H NHAc H H H C14 H NHMs H H H C15 H N (Ms) CH ₂ CH = CMe ₂ H H H C16 H OH H H OCH ₂ C ₆ H ₅ C17 H OMs H H and ₂ c ₆ h ₅ C18 H OH H H OCH ₂ CH = CMe ₂ C19 H About me H H OCH ₂ CH = CMe ₂ C20 H OMs H H OCH ₂ CH = CMe ₂ C21 no ₂ H H H H C22 nh ₂ H H H H C23 NHAc H H H H C24 NHMs H H H H C25 Cl H H H no ₂ C26 Cl H H H nh ₂ C27 Cl H H H NHMs C28 Cl H H H NHCOCF3 C29 Cl H H H NHCH ₂ CH = CMe ₂ C30 H H H H NHCH ₂ CH = CMe ₂

151

Table 56 • ·· 000000

0 0 0 0 0 0

0 0 ·· 0 0 00000 0 0 0 0 0 0 0 0 00 00 00 0

S11

No. - / b \ - _W 2 y R8 R9 Rio Rn AND C Ia-1 SI H H H - A6 C2 Ia-2 SI H H H - A32 C2 Ia-3 SI H H H - A35 C2 Ia-4 SI H H H - A6 C3 Ia-5 SI H H H - A8 C3 Ia-6 SI H H H - A33 C3 Ia-7 SI H H H - A35 C3 Ia-8 SI H H H - A6 C4 Ia-9 SI H H H - A8 C4 Ia-10 SI H H H - A32 C4 Ia-11 SI H H H - A33 C4 Ia-12 SI H H H - A8 C17 Ia-13 SI H H H - A32 C18 Ia-14 SI H H H - A33 C19 Ia-15 si H H Cl - A6 C2 Ia-16 si H H Cl - A32 C2 Ia-17 si H H Cl - A8 C3 Ia-18 SI H H Cl - A33 C3 Ia-19 si H H Cl - A35 C6 Ia-20 SI Me H H - A6 C2 Ia-21 SI Me H H - A32 C2 Ia-22 si Me H H - A35 C2 Ia-23 SI Me H H - A6 C3 Ia-24 SI Me H H - A8 C3 Ia-25 SI Me H H - A33 C3 Ia-26 si Me H H - A35 C3 Ia-27 si H Me H - A6 C2

152

Table 57

ΦΦΦΦ ·· ·· • · · Φ Φ

• 99 • ·

Φ Φ Φ · Φ ·

Φ Φ «ΦΦΦ

99 · 100 «·

No. - <B> - w ² - / R8 R9 R ¹⁰ Ru AND C Ia-28 SI H Me H - A32 C2 Ia-29 SI H Me H - A35 C2 Ia-30 Sl H Me H - A6 C3 Ia-31 Sl H Me H - A8 C3 Ia-32 si H Me H - A33 C3 Ia-33 Sl H Me H - A35 C3 Ia-34 Sl H H Me - A6 C2 Ia-35 Sl H H Me - A32 C2 Ia-36 Sl H H Me - A35 C2 Ia-37 Sl H H Me - A6 C3 Ia-38 Sl H H Me - A8 C3 Ia-39 Sl H H Me - A33 C3 Ia-40 Sl H H Me - A35 C3 Ia-41 Sl H Me Me - A6 C2 Ia-42 Sl H Me Me - A32 C2 Ia-43 Sl H Me Me - A35 C2 Ia-44 si H Me Me - A37 C2 Ia-45 Sl H Me Me - A6 C3 Ia-46 Sl H Me Me - A8 C3 Ia-47 Sl H Me Me - A33 C3 Ia-48 Sl H Me Me - A35 C3 Ia-49 Sl H Me Me - A6 C6 Ia-50 Sl H Me Me - A32 C6 Ia-51 Sl H Me Me - A34 C6 Ia-52 si H Me Me - A35 C6 Ia-53 Sl H Me Me - A36 C6 Ia-54 Sl H Me Me - A37 C6 Ia-55 Sl H Me Me - A38 C6 Ia-56 Sl Me Me Me - A6 C2 Ia-57 si Me Me Me - A32 C2 Ia-58 Sl Me Me Me - A35 C2 Ia-59 Sl Me Me Me - A37 C2 Ia-60 Sl Me Me Me - A6 C3 Ia-61 si Me Me Me - A8 C3 Ia-62 Sl Me Me Me - A33 C3 Ia-63 Sl Me Me Me - A35 C3 Ia-64 S2 H H - H A6 C2

153 • 99 ·· ···· • 99 99 · 9 9 · · 9

98 «9 · · ·

9 9 9 9 • 99 99 9 9

Table 58

No. —Γβ \ - VI ² - ' R8 R9 Rio Rn AND C Ia-65 S2 H H - H A8 C2 Ia-66 S2 H H - H A32 C2 Ia-67 S2 H H - H A35 C2 Ia-68 S2 H H - H A8 C3 Ia-69 S2 H H - H A33 C3 Ia-70 S2 H H - H A35 C3 Ia-71 S2 Me H - H A6 C2 Ia-72 S2 Me H - H A8 C2 Ia-73 S2 Me H - H A32 C2 Ia-74 S2 Me H - H A35 C2 Ia-75 S2 Me H - H A8 C3 Ia-76 S2 Me H - H A33 C3 Ia-77 S2 Me H - H A35 C3 Ia-78 S2 H Me - H A6 C2 Ia-79 S2 H Me - H A8 C2 Ia-80 S2 H Me - H A32 C2 Ia-81 S2 H Me - H A35 C2 Ia-82 S2 H Me - H A8 C3 Ia-83 S2 H Me - H A33 C3 Ia-84 S2 H Me - H A35 C3 Ia-85 S2 H H - Me A6 C2 Ia-86 S2 H H - Me A8 C2 Ia-87 S2 H H - Me A32 C2 Ia-88 S2 H H - Me A35 C2 Ia-89 S2 H H - Me A8 C3 Ia-90 S2 H H - Me A33 C3 Ia-91 S2 H H - Me A35 C3 Ia-92 S2 Me H - Me A6 C2 Ia-93 S2 Me H - Me A8 C2 Ia-94 S2 Me H - Me A32 C2 Ia-95 S2 Me H - Me A35 C2 Ia-96 S2 Me H - Me A8 C3 Ia-97 S2 Me H - Me A33 C3 Ia-98 S2 Me H - Me A35 C3 Ia-99 S2 Me H - Me A6 C6 Ia-100 S2 Me H - Me A32 C6 Ia-101 S2 Me H - Me A34 C6

· ♦ 0 0 0 0

155 • 0 · · 0 0 0 0

00000 0 ·

0 0 0 0

Table 59

No. —FlvV w ² - ⁷ R8 R9 Ri ° Rn AND C Ia-102 S2 Me H - Me A35 C6 Ia-103 S2 Me H - Me A36 C6 Ia-104 S2 Me H - Me A37 C6 Ia-105 S2 Me H - Me A38 C6 Ia-106 S2 Me Me - Me A6 C2 Ia-107 S2 Me Me - Me A8 C2 Ia-108 S2 Me Me - Me A32 C2 Ia-109 S2 Me Me - Me A35 C2 Ia-110 S2 Me Me - Me A8 C3 Ia-111 S2 Me Me - Me A33 C3 Ia-112 S2 Me Me - Me A35 C3 Ia-113 S2 Me Me - Me A6 C6 Ia-114 S2 Me Me - Me A32 C6 Ia-115 S2 Me Me - Me A34 C6 Ia-116 S2 Me Me - Me A35 C6 Ia-117 S2 Me Me - Me A37 C6 Ia-118 S3 Me - H - A6 C2 Ia-119 S3 Me - H - A32 C2 Ia-120 S3 Me - H - A35 C2 Ia-120 S3 About me - H - A6 C2 Ia-121 S3 About me - H - A32 C2 Ia-122 S3 About me - H - A35 C2 Ia-123 S3 Me - Me - A6 C2 Ia-124 S3 Me - Me - A32 C2 Ia-125 S3 Me - About me - All Cl Ia-126 S3 Me - Me - A35 C2 Ia-127 S3 Me - About me - A3 Cl Ia-128 S3 Me - About me - A4 Cl Ia-129 S3 Me - About me - A5 Cl Ia-131 S3 Me - About me - A6 Cl Ia-132 S3 Me - About me - A7 Cl Ia-133 S3 Me - About me - A8 Cl Ia-134 S3 Me - About me - A9 Cl Ia-135 S3 Me - About me - A10 Cl Ia-136 S3 Me - About me - A12 whose Ia-137 S3 Me - About me - A13 Cl Ia-138 S3 Me - About me - A14 whose Ia-139 S3 Me - About me - A15 whose

ftft ftftftft ·

155

Table 60 ♦ ft «ft ftft ftft ftft ftft ftft · • · ftftft ftftftft • ftft ftft ftftft ftftftft

No. - (b \ - w ² - / R8 R9 R ¹⁰ Rn AND C Ia-140 S3 Me - About me - A16 Cl Ia-141 S3 Me - About me - A17 Cl Ia-142 S3 Me - About me - A18 Cl Ia-143 S3 Me - About me - A19 Cl Ia-144 S3 Me - About me - A20 Cl Ia-145 S3 Me - About me - A21 Cl Ia-146 S3 Me - About me - A22 Cl Ia-147 S3 Me - About me - A23 Cl Ia-148 S3 Me - About me - A24 Cl Ia-149 S3 Me - About me - A25 Cl Ia-150 S3 Me - About me - A26 Cl Ia-151 S3 Me - About me - A27 Cl Ia-152 S3 Me - About me - A28 Cl Ia-153 S3 Me - About me - A29 whose Ia-154 S3 Me - About me - A30 Cl Ia-155 S3 Me - About me - A31 Cl Ia-156 S3 Me - About me - A32 Cl Ia-157 S3 Me - About me - A33 Cl Ia-158 S3 Me - About me - A35 Cl Ia-159 S3 Me - About me - A39 Cl Ia-160 S3 Me - About me - A40 Cl Ia-161 S3 Me - About me - A6 C2 Ia-162 S3 Me - About me - A8 C2 Ia-163 S3 Me - About me - A32 C2 Ia-164 S3 Me - About me - A33 C2 Ia-165 S3 Me - About me - A35 C2 Ia-166 S3 Me - About me - A37 C2 Ia-167 S3 Me - About me - A8 C3 Ia-168 S3 Me - About me - A33 C3 Ia-169 S3 Me - About me - A32 C4 Ia-170 S3 Me - About me - A35 C4 Ia-171 S3 Me - About me - A32 C6 Ia-172 S3 Me - About me - A35 C6 Ia-173 S3 Me - About me - A8 C7 Ia-174 S3 Me - About me - A32 C7 Ia-175 S3 Me - About me - A8 C8 Ia-176 S3 Me - About me - A8 C9 Ia-177 S3 Me - About me - A32 C9 Ia-178 S3 Me - About me - A33 C9

156

Table 61 • ti titi ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti

No. - <b \ w ² -Z R8 R9 Rio Ru AND C Ia-179 S3 Me - About me - A8 CIO Ia-180 S3 Me - About me - A32 CIO Ia-181 S3 Me - About me - A33 CIO Ia-182 S3 Me - About me - A6 Target Ia-183 S3 Me - About me - A8 cn Ia-184 S3 Me - About me - A8 C12 Ia-185 S3 Me - About me - A8 C13 Ia-186 S3 Me - ' About me - A8 C14 Ia-187 S3 Me - About me - A32 C14 Ia-188 S3 Me - About me - A8 C15 Ia-189 S3 Me - About me - A32 C15 Ia-190 S3 Me - About me - A33 C15 Ia-191 S3 Me - About me - A6 C21 Ia-192 S3 Me - About me - A8 C21 Ia-193 S3 Me - About me - A6 C22 Ia-194 S3 Me - About me - A8 C23 Ia-195 S3 Me - About me - A32 C23 Ia-196 S3 Me - About me - A33 C23 Ia-197 S3 Me - About me - A8 C24 Ia-198 S3 Me - OEt - A6 Cl Ia-199 S3 Me - OEt - A8 Cl Ia-200 S3 Me - OEt - A14 Cl Ia-201 S3 Me - OEt - A17 Cl Ia-202 S3 Me - OEt - A32 Cl Ia-203 S3 Me - OEt - A33 Cl Ia-204 S3 Me - OEt - A6 C2 Ia-205 S3 Me - OEt - A32 C2 Ia-206 S3 Me - O ^J Pr - A6 Cl Ia-207 S3 Me - O ^y Pr - A8 Cl Ia-208 S3 Me - O'Pr - A14 Cl Ia-209 S3 Me - 0'Pr - A17 Cl Ia-210 S3 Me - O'Pr - A32 Cl Ia-211 S3 Me - O'Pr - A33 Cl Ia-212 S3 Me - O'Pr - A6 C2 Ia-213 S3 Me - O'Pr - A32 C2 Ia-214 S3 Et - About me - A6 Cl Ia-215 S3 Et - About me - A8 Cl Ia-216 S3 Et - About me - A14 Cl Ia-217 S3 Et - About me - A17 Cl

157

Table 62 • φ · · · · «φ φ φ • • · · · · · · · · · · · · φ φ φ φ «· φ

No. - <B> - 'N ² ' R8 R9 Ri ° Rn AND C Ia-218 S3 Et - About me - A32 Cl Ia-219 S3 Et - About me - A33 Cl Ia-220 S3 Et - About me - A6 C2 Ia-221 S3 Et - About me - A32 C2 Ia-222 S3 H - CO ₂ H - A6 Cl Ia-223 S3 H - CO2H - A8 Cl Ia-224 S3 H - CO2H - A32 Cl Ia-225 S3 H - CO2H - A33 Cl Ia-226 S3 H - CO ₂ Me - A6 Cl Ia-227 S3 H - COžMe - A8 Cl Ia-228 S3 H - CO2Me - All Cl Ia-229 S3 H - COaMe - A32 Cl Ia-230 S3 H - COaMe - A33 Cl Ia-231 S3 H - CHaOH - A32 Cl Ia-232 S3 H - CHaOAc - A8 Cl Ia-233 S3 Me - SMe - A8 Cl Ia-234 S3 Me - SMe - A32 Cl Ia-235 S3 Me - NHMe - A6 Cl Ia-236 S3 Me - NHMe - A8 Cl Ia-237 S3 Me - NHMe - A32 Cl Ia-238 S4 - Me - About me A32 C2 Ia-239 S4 - Me - About me A6 C3 Ia-240 S4 - Me - About me A8 C3 Ia-241 S4 - Me - About me A33 C3 Ia-242 S4 - Me - About me A35 C6 Ia-243 S4 - Me Me A32 C2 Ia-244 S4 - Me - Me A6 C3 Ia-245 S4 - Me - Me A8 C3 Ia-246 S4 - Me - Me A33 C3 Ia-247 S4 - Me - Me A35 C6 Ia-248 S5 H H - - A6 Cl Ia-249 S5 H H - - A8 Cl Ia-250 S5 H H - - A32 Cl Ia-251 S5 H H - - A33 Cl Ia-252 S5 H H - - A32 C2 Ia-253 S5 H H - - A8 C3 Ia-254 S5 H H - - A33 C3 Ia-255 S5 H H - - A6 C4 Ia-256 S5 H H - - A8 C4 Ia-257 S5 H H - - A32 C4

158

Table 63 • 49 44 4444 44 99

4 4 4 4 ♦ ·· ·

499 94 * 9494 • 444 99 44 94 49

4,499 9949

449 44 94 9 49

No. - (b \ - w ² - / R8 R9 Ri ° Rn AND C Ia-258 S5 H H - - A33 C4 Ia-259 S5 H H - - A35 C6 Ia-260 S5 Me Me - - A32 C2 Ia-261 S5 Me Me - - A35 C2 Ia-262 S5 Me Me - - A35 C6 Ia-26.3 S6 H - - H A32 C2 Ia-264 S6 H - - H A35 C2 Ia-265 S6 H - - H A35 C6 Ia-266 S6 Me - - Me A32 C2 Ia-267 S6 Me - Me A35 C2 Ia-268 S6 Me - - Me A35 C6 Ia-269 S7 H H - - A6 C2 Ia-270 S7 H H - - A8 C2 Ia-271 S7 H H - - A32 C2 Ia-272 S7 H H - - A8 C3 Ia-273 S7 H H - - A33 C3 Ia-274 S7 H H - - A35 C6 Ia-275 S7 H H - - A6 C16 Ia-276 S7 Me H - - A8 C2 Ia-277 S7 Me H - - A32 C2 Ia-278 S7 Me H - - A8 C3 Ia-279 S7 Me H - - A33 C3 Ia-280 S7 H Me - - A8 C2 Ia-281 S7 H Me - - A32 C2 Ia-282 S7 H Me - - A8 C3 Ia-283 S7 H Me - - A33 C3 Ia-284 S7 Me Me - - A8 C2 Ia-285 S7 Me Me - - A32 C2 Ia-286 S7 Me Me - - A8 C3 Ia-287 S7 Me Me - - A33 C3 Ia-288 S7 Me Me - - A35 C6 Ia-289 S8 H H - - A32 C2 Ia-290 S8 H H - - A35 C2 Ia-291 S8 H H - - A35 C6 Ia-292 S8 Me H - - A32 C2 Ia-293 S8 Me H - - A35 C2 Ia-294 S8 Me H - - A35 C6 Ia-295 S8 H Me - - A32 C2 Ia-296 S8 H Me - - A35 C2 Ia-297 S8 H Me - - A35 C6

159

Table 64 φ φ φ φ φ φ · φ · φ φ

ΦΦ ΦΦ ΦΦ 9

Φ ♦ Φ Φ Φ

Φ · Φ ·

Φ Φ Φ Φ

Φ Φ Φ Φ

Φ Φ ΦΦ

No. _w ² y R8 R9 Ri ° Rn AND C Ia-298 S8 Me Me - - A32 C2 Ia-299 S8 Me Me - - A35 C2 Ia-300 S8 Me Me - - A35 C6 Ia-301 S9 Me Me - - A6 Cl Ia-302 S9 Me Me - - A8 Cl Ia-303 S9 Me Me - - A32 Cl Ia-304 S9 Me Me - - A33 Cl Ia-305 S9 Me Me - - A6 C4 Ia-306 S9 Me Me - - A8 C4 Ia-307 S9 Me Me - - A32 C4 Ia-308 S9 Me Me - - A33 C4 Ia-309 S9 Me About me - - A6 Cl Ia-310 S9 Me About me - - A8 Cl Ia-311 S9 Me About me - - A14 Cl Ia-312 S9 Me About me - - A17 Cl Ia-313 S9 Me About me - - A32 Cl Ia-314 S9 Me About me - - A33 Cl Ia-315 S9 Me About me - - A6 C4 Ia-316 S9 Me About me - - A8 C4 Ia-317 S9 Me About me - - A14 C4 Ia-318 S9 Me About me - - A17 C4 Ia-319 S9 Me About me - - A32 C4 Ia-320 S9 Me About me - - A33 C4 Ia-321 S9 Me About me - - A35 C4 Ia-322 S9 Me CO ₂ H - - A33 C4 Ia-323 S9 Me CO2Et - - A6 C4 Ia-324 S9 Me CO ₂ Et - - A8 C4 Ia-325 S9 Me CO ₂ Et - - A32 C4 Ia-326 S9 Me CO ₂ Et - - A33 C4 Ia-327 S9 Me CO ₂ Et - - A35 C4 Ia-328 S9 Me CH2OH - - A32 C4 Ia-329 S9 Me CH2OH - - A35 C4 Ia-330 S10 H - - - A6 Cl Ia-331 S10 H - - - A8 Cl Ia-332 S10 H - - - A32 Cl Ia-333 S10 H - - - A33 Cl Ia-334 S10 Me - - - A6 Cl Ia-335 S10 Me - - - A8 Cl Ia-336 sio Me - - - A32 Cl

• 44 4494

4 4 9 4

4 4 4 4 4

4 4 9 4

445 49 44 0

160

4 9

99

Table 65

No. - (b \ - W ² - / R8 R9 Rio Rn AND C Ia-337 S10 Me - - - A33 Cl Ia-338 Sil H - - - A6 Cl Ia-339 Sil H - - - A8 Cl Ia-340 Sil H - - - A14 Cl Ia-341 Sil H - - - A17 Cl Ia-342 Sil H - - - A32 Cl Ia-343 Sil H - - - A33 Cl Ia-344 Sil Me - - - A6 Cl Ia-345 sii Me - - - A8 Cl Ia-346 Sil Me - - - A32 Cl Ia-347 sii Me - - - A33 Cl Ia-348 S12 H - - - A6 Cl Ia-349 S12 H - - - A8 whose Ia-350 S12 H - - - A32 Cl Ia-351 S12 H - - - A33 Cl Ia-352 S12 Me - - - A6 Cl Ia-353 S12 Me - - - A8 Cl Ia-354 S12 Me - - - A32 Cl Ia-355 S12 Me - - - A33 Cl Ia-356 S2 Me H - Me A37 C30 Ia-357 SI H Me Me - A37 C30

161

Table 66 • · 99999999 9 »··

9 · 99 99 9999 • 99 99 99 9 · ·

999 99 99 99 9 · 9 • 9 999 9999

999 99 ·· · 9 99

No. w ³ - ' R12 R13 Ri " R15 X'-Y ’ (B) AND Ib-1 TI H H - H H B2 A6 Ib-2 TI H H - H H B3 A8 Ib-3 TI H H - H H B2 A32 Ib-4 TI H H - H H B3 A33 Ib-5 TI H H - H H B2 A35 Ib-6 TI H H - H H B4 All Ib-7 TI H H - H H B4 A32 Ib-8 TI H H - H H B4 A35 Ib-9 TI H H - H H B4 Al Ib-10 TI H H - H H B4 A41 Ib-11 TI H H - H N (COCF ₃ ) CH ₂ CH = CMe ₂ B3 A33 Ib-12 TI H H - H NH ₂ B3 A8 Ib-13 TI H H - H nh ₂ B4 A35 Ib-14 TI H H - H nh ₂ B4 Al Ib-15 TI H H - H nh ₂ B4 A41 Ib-16 TI H H - H NHCH ₂ CH = CMe ₂ B2 A32 Ib-17 TI H H - H NHCH ₂ CH = CMe ₂ B4 A35 Ib-18 TI H H - H NHCH ₂ CH = CMe ₂ BI A41 Ib-19 TI H H - H NHCH ₂ CH = CMe ₂ B4 Al Ib-20 TI H H - H NHCH ₂ CH = CMe ₂ B4 A41

fcfcfc

162

Fcfc fcfc fcfc fcfc fcfc fcfc fcfc fcfcfcfc fcfcfc fcfc

No. CD ^- w ^3-7 R12 Ris R14 Ris X’-Y ’ (B) AND Ib-21 TI H H - H NHCOCFs B3 A8 Ib-22 TI H H - H NHCOCF3 B3 A33 Ib-23 TI H H - H NHCOCFs B4 A35 Ib-24 TI H H - H NHCOCFs B4 Al Ib-25 TI H H - H NHCOCFs B4 A41 Ib-26 TI H H - H NHCOMe B2 A32 Ib-27 TI H H - H NHCOMe B3 A33 Ib-28 TI H H - H NHCOMe B4 A35 Ib-29 TI H H - H NHCOMe B4 Al Ib-30 TI H H - H NHCOMe B4 A41 Ib-31 TI H H - H NHSO ₂ Et Bl A41 Ib-32 TI H H - H NHSOaEt B4 Al Ib-33 TI H H - H NHSOaEt B4 A41 Ib-34 TI H H - H NHMs B2 A32 Ib-35 TI H H - H NHMs Bl A41 Ib-36 TI H H - H NHMs B4 Al Ib-37 TI H H - H NHMs B4 A41 Ib-38 TI H H - H NMe ₂ B2 A6 Ib-39 TI H H - H NMe ₂ B3 A8 Ib-40 TI H H - H NMe ₂ B2 A32 Ib-41 TI H H - H NMe ₂ B3 A33 Ib-42 TI H H - H NMe ₂ B2 A35 Ib-43 TI H H - H NMe ₂ B4 A32 Ib-44 TI H H - H NMe ₂ B4 A35 Ib-45 TI H H - H NMe ₂ B5 A32 Ib-46 TI H H - H NO ₂ B2 A6 Ib-47 TI H H - H no ₂ B3 A8 Ib-48 TI H H - H no ₂ B4 Al Ib-49 TI H H - H no ₂ B4 A41 Ib-50 T2 H H H - Cl B4 Al Ib-51 T2 H H H - Cl B4 A41 Ib-52 T2 H H H - H B2 A6 Ib-53 T2 H H H - H B3 A8 Ib-54 T2 H H H - H B2 A32 Ib-55 T2 H H H - H B3 A33 Ib-56 T2 H H H - H B2 A35 Ib-57 T2 H H H - H B4 A32 Ib-58 T2 H H H - H B4 A35 Ib-59 T2 H H H - H B4 Al Ib-60 T2 H H H - H B4 A41

163

Table 68

• 0 0 0 0 0 0 · • 0 00 0 0 0 0 « « 0 0 0 «00 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 · • 0 0 • 00 • 0

No. Q w ^3-7 R12 R13 Ri " R1 ⁵ X'-Y ' (B) AND Ib-61 T2 H H H - nh ₂ B2 A6 Ib-62 T2 H H H - nh ₂ B3 A8 Ib-63 T2 H H H - nh ₂ BI A41 Ib-64 T2 H H H - nh ₂ B4 Al Ib-65 T2 H H H - nh ₂ B4 A41 Ib-66 T2 H H Me - nh ₂ B4 Al Ib-67 T2 H H Me - nh ₂ B4 A41 Ib-68 T2 H H H - NHCH ₂ CH = CMe ₂ B4 Al Ib-69 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A41 Ib-70 T2 H H Me - NHCH ₂ CH = CMe ₂ B4 Al Ib-71 T2 H H Me - NHCH ₂ CH = CMe ₂ B4 A41 Ib-72 T2 H H H - NHCOMe B4 Al Ib-73 T2 H H H - NHCOMe B4 A41 Ib-74 T2 H H Me - NHCOMe B4 Al Ib-75 T2 H H Me - NHCOMe B4 A41 Ib-76 T2 H H H - NHMs B4 Al Ib-77 T2 H H H - NHMs B4 A41 Ib-78 T2 H H Me - NHMs B4 Al Ib-79 T2 H H Me - NHMs B4 A41 Ib-80 T2 H H H - NMe ₂ B2 A6 Ib-81 T2 H H H - NMe ₂ B3 A8 Ib-82 T2 H H H - NMe ₂ B2 A32 Ib-83 T2 H H H - NMe ₂ B3 A33 Ib-84 T2 H H H - NMe ₂ B4 A32 Ib-85 T2 H H H - NMe ₂ B4 A35 Ib-86 T2 H H H - OCH ₂ C ₆ H ₅ B4 Al Ib-87 T2 H H H - OCH ₂ C ₆ H5 B4 A41 Ib-88 T2 H H H - OCH ₂ CH = CMe ₂ BI A41 Ib-89 T2 H H H - OCH ₂ CH = CMe ₂ B4 Al Ib-90 T2 H H H - OCH ₂ CH = CMe ₂ B4 A41 Ib-91 T2 H H H - About me B2 A6 Ib-92 T2 H H H - About me B3 A8 Ib-93 T2 H H H - About me B2 A32 Ib-94 T2 H H H - About me B3 A33 Ib-95 T2 H H H - About me B2 A35 Ib-96 T2 H H H - About me B4 A32 Ib-97 T2 H H H - About me B4 A35 Ib-98 T2 H H H - Ms B4 Al Ib-99 T2 H H H - Ms B4 A41 Ib-100 T3 H H H H - B2 A6

164

Table 69

• 0 * 00 ···· 0 * 0 0 0 0 0 0 »» 0 0 0 000 0 0 0 0 • 0 0 • • 0 • 0 0 0 0 0 00 00 0 * 0 «0

»0

No. _w 3 7 R12 R ¹³ R14 R ¹⁵ X’-Y ' (B) AND Ib-101 T3 H H H H - B2 A32 Ib-102 T3 H H H H - B2 A35 Ib-103 T3 H H H H - B3 A8 Ib-104 T3 H H H H - B3 A33 Ib-105 T3 H H H H - B4 All Ib-106 T3 H H H H - B4 A32 Ib-107 T3 H H H H - B4 A35 Ib-108 T3 H H H H - B4 A37 Ib-109 T3 H H H H - B4 A38 Ib-110 T3 H H H H - B4 Al Ib-111 T3 H H H H - B4 A41 Ib-112 T4 H H - H - B3 A8 Ib-113 T4 H H - H - B2 A32 Ib-114 T4 H H - H - B3 A33 Ib-115 T4 H H - About me - B4 Al Ib-116 T4 H H - About me - B4 A41 Ib-117 T4 H Cl - H - B2 A6 Ib-118 T4 H Cl - H - B3 A8 Ib-119 T4 H Cl - H - B3 A33 Ib-120 T4 H Cl - H - B4 Al Ib-121 T4 H Cl - H - B4 A41 Ib-122 T4 H OH - H - B4 Al Ib-123 T4 H OH - H - B4 A41 Ib-124 T4 H About me - H - B2 A32 Ib-125 T4 H About me - H - B4 A35 Ib-126 T4 H About me - H - B4 Al Ib-127 T4 H About me - H - B4 A41 Ib-128 T5 H - H - H B2 A32 Ib-129 T5 H - H - H B3 A33 Ib-130 T5 H - H - H B4 A35 Ib-131 T5 H - H - OH B4 A35 Ib-132 T5 H - H - OCH ₂ C ₆ H ₅ B4 Al Ib-133 T5 H - H - OCHžCeHs B4 A41 Ib-134 T5 H - H - OCH ₂ CH = CMe ₂ B4 Al Ib-135 T5 H - H - OCH ₂ CH = CMe ₂ B4 A41 Ib-136 T5 H - H - NMe ₂ B2 A32 Ib-137 T5 H - H - NMe ₂ B4 A35 Ib-138 T5 H - H - NHCH ₂ CH = CMe ₂ B4 Al Ib-139 T5 H - H - NHCH ₂ CH = CMe ₂ B4 A41 Ib-140 T6 - H - H H B2 A32

β · ···

165

Table 70 · and «· ♦> ft ft ft ft ft ft ft <<♦ ♦ ♦ ft ft ft ft ft ft ft ft ft ft ft ft ft ft ft · · Aft

No. Q w ^3-7 R12 R ¹³ R ¹⁴ R1 ⁵ X’-Y ' (B) AND Ib-141 T6 - H - H H B4 A35 Ib-142 T7 H H - - H B2 A32 Ib-143 T7 H H - - H B3 A33 Ib-144 T7 H H - - Cl B2 A6 Ib-145 T7 H H - - Cl B3 A8 Ib-146 T7 H H - - Cl B2 A32 Ib-147 T7 H H - - Cl B3 A33 Ib-148 T7 H H - - Cl B4 A35 Ib-149 T7 H H - - Cl B4 Al Ib-150 T7 H H - - Cl B4 A41 Ib-151 T7 H H - - NHCH ₂ CH = CMe ₂ B4 Al Ib-152 T7 H H - - NHCH ₂ CH = CMe ₂ B4 A41 Ib-153 T7 H H - - NMe ₂ B2 A6 Ib-154 T7 H H - - NMe ₂ B3 A8 Ib-155 T7 H H - - NMe ₂ B2 A32 Ib-156 T7 H H - - NMe ₂ B3 A33 Ib-157 T7 H H - - NMe ₂ B4 A35 Ib-158 T7 H H - - OCH ₂ C ₆ H ₅ B4 Al Ib-159 T7 H H - - OCHaCsHe B4 A41 Ib-160 T7 H H - - OCH ₂ CH = CMe ₂ B4 Al Ib-161 T7 H H - - OCH ₂ CH = CMe ₂ B4 A41 Ib-162 T7 H H - - About me B2 A32 Ib-163 T7 H H - - About me B4 A35 Ib-164 T7 H H - - About me B4 Al Ib-165 T7 H H - - About me B4 A41 Ib-166 T8 H - - H H B2 A6 Ib-167 T8 H - - H H B3 A8 Ib-168 T8 H - - H H B2 A32 Ib-169 T8 H - - H H B3 A33 Ib-170 T8 H - - H H B4 A35 Ib-171 T8 H - - H About me B2 A32 Ib-172 T8 H - - H About me B4 A35 Ib-173 T8 H - - H NMe ₂ B2 A32 Ib-174 T8 H - - H NMe ₂ B4 A35 Ib-175 T8 H - - H Cl B4 Al Ib-176 T8 H - - H Cl B4 A41 Ib-177 T8 H - - H OCH ₂ C ₆ H ₅ B4 Al Ib-178 T8 H - - H OCH ₂ C ₆ H ₅ B4 A41 Ib-179 T8 H - - H OCH ₂ CH = CMe ₂ B4 Al Ib-180 T8 H - - H OCH ₂ CH = CMe ₂ B4 A41

• · · · · · β ·

166

Table 71

No. <£> - _w 3_y R12 R13 R1 ⁴ R15 X'-Y ’ (B) AND Ib-181 T8 H - - H NHCH ₂ CH = CMe ₂ B4 Al Ib-182 T8 H - - H NHCH ₂ CH = CMe ₂ B4 A41 Ib-183 T9 H OCH2C6H5 - - - B4 Al Ib-184 T9 H OCH ₂ C ₆ H ₅ - - - B4 A41 Ib-185 T9 H OCH ₂ CH = CMe ₂ - - - B4 Al Ib-186 T9 H OCH ₂ CH = CMe ₂ - - - B4 A41 Ib-187 T9 H NH ₂ - - - B4 Al Ib-188 T9 H nh ₂ - - - B4 A41 Ib-189 T9 H NHCH ₂ CH = CMe ₂ - - - B4 Al Ib-190 T9 H NHCH ₂ CH = CMe ₂ - - B4 A41 Ib-191 T9 H NHMs - - - B4 Al Ib-192 T9 H NHMs - - - B4 A41 Ib-193 T10 H OCH ₂ C ₆ H ₅ - - - B4 Al Ib-194 T10 H OCH ₂ C ₆ H ₅ - - - B4 A41 Ib-195 T1O H OCH ₂ CH = CMe ₂ - - - B4 Al Ib-196 T1O H OCH ₂ CH = CMe ₂ - - - B4 A41 Ib-197 T1O H NH ₂ - - - B4 Al Ib-198 T1O H nh ₂ - - - B4 A41 Ib-199 T1O H NHCH ₂ CH = CMe ₂ - - - B4 Al Ib-200 T1O H NHCH ₂ CH = CMe ₂ - - - B4 A41 Ib-201 T1O H NHMs - - - B4 Al Ib-202 T1O H NHMs - - - B4 A41 Ib-203 Til H H H H - B2 A6 Ib-204 Til H H H H - B3 A8 Ib-205 Til H H H H - B2 A32 Ib-206 Til H H H H - B3 A33 Ib-207 TI H H - H NHCH ₂ CH = CMe ₂ B4 A37 Ib-208 TI H H H nh ₂ B4 A37 Ib-209 TI H H H no ₂ B4 A37 Ib-210 TI H H H H B4 A5 lb-211 TI H H H H B4 A37 Ib-212 TI H H H NH-cHex B4 A37 Ib-213 TI H H - H About me B4 A37 Ib-214 TI H H H OCH ₂ CH = CMe ₂ B4 A37 Ib-215 TI H H - H nh ₂ B7 A37 Ib-216 TI H H - H NHCH ₂ CH = CMe ₂ B7 A37 Ib-217 TI H H - H OH B7 A37

• ·

167

Table 72

No. vj ³ - ' R12 R13 R1 ⁴ Ris X'-Y ’ (B) AND Ib-218 T2 H H H - OCH ₂ CH = CMe ₂ BI A64 Ib-219 T2 H H H - OCH ₂ CH = CMe ₂ BI A65 Ib-220 T2 H H H - OCH ₂ CH = CMe ₂ BI A75 Ib-221 T2 H H H - OCH ₂ CH = CMe ₂ BI A76 Ib-222 T2 H H H - OCH ₂ CH = CMe ₂ BI A67 Ib-223 T2 H H H - OCH ₂ CH = CMe ₂ BI A77 Ib-224 T2 H H H - OCH ₂ CH = CMe ₂ B4 A64 Ib-225 T2 H H H - OCH ₂ CH = CMe ₂ B4 A65 Ib-226 T2 H H H - OCH ₂ CH = CMe ₂ B4 A69 Ib-227 T2 H H H - OCH ₂ CH = CMe ₂ B4 A76 Ib-228 T2 H H H - OCH ₂ CH = CMe ₂ B4 A83 Ib-229 T2 H H H - OCH ₂ CH = CMe ₂ B4 A82 Ib-230 T2 H H H - OCH ₂ CH = CMe ₂ B4 A81 Ib-231 T2 H H H - OCH ₂ CH = CMe ₂ B4 A69 Ib-232 T2 H H H - OCH ₂ CH = CMe ₂ B4 A68 Ib-233 T2 H H H - OCH ₂ CH = CMe ₂ B4 A66 Ib-234 T2 H H H - OCH ₂ CH = CMe ₂ B4 A71 Ib-235 T2 H H H - OCH ₂ CH = CMe ₂ B4 A72 Ib-236 T2 H H H - OCH ₂ CH = CMe ₂ B4 A73 Ib-237 T2 H H H - OCH ₂ CH = CMe ₂ B4 A74 Ib-238 T2 H H H - OCH ₂ CH = CMe ₂ B4 A104 Ib-239 T2 H H H - OCH ₂ CH = CMe ₂ B4 A45 Ib-240 T2 H H H - OCH ₂ CH = CMe ₂ B4 A47 Ib-241 T2 H H H - OCH ₂ CH = CMe ₂ B4 A49 Ib-242 T2 H H H - OCH ₂ CH = CMe ₂ B4 A48 Ib-243 T2 H H H - OCH ₂ CH = CMe ₂ B4 A53 Ib-244 T2 H H H - OCH ₂ CH = CMe ₂ B4 A5O Ib-245 T2 H H H - OCH ₂ CH = CMe ₂ B4 A59 Ib-246 T2 H H H - OCH ₂ CH = CMe ₂ B4 A57 Ib-247 T2 H H H - OCH ₂ CH = CMe ₂ B4 A55 Ib-248 T2 H H H - OCH ₂ CH = CMe ₂ B4 A42 Ib-249 T2 H H H - OCH ₂ CH = CMe ₂ B4 A43 Ib-250 T2 H H H - OCH ₂ CH = CMe ₂ B4 A67 Ib-251 T2 H H H - OCH ₂ CH = CMe ₂ B4 A62 Ib-252 T2 H H H - OCH ₂ CH = CMe ₂ B4 A63

• · <

• I

168

Table 73 ··· ·· ·· «

No. CD ^- _w ³ _v R12 R ¹³ R1 ⁴ R15 X'-Y ' (B) AND Ib-253 T2 H H H - OCH ₂ CH = CMe ₂ B4 A78 Ib-254 T2 H H H - OCH ₂ CH = CMe ₂ B4 A79 Ib-255 T2 H H H - OCH ₂ CH = CMe ₂ B4 A84 Ib-256 T2 H H H - OCH ₂ CH = CMe ₂ B4 A85 Ib-257 T2 H H H - OCH ₂ CH = CMe ₂ B4 A60 Ib-258 T2 H H H - OCH ₂ CH = CMe ₂ B4 A61 Ib-259 T2 H H H - OCH ₂ CH = CMe ₂ B4 A46 Ib-260 T2 H no ₂ H - OCH ₂ CH = CMe ₂ B4 A46 Ib-261 T2 H H H - OCH ₂ CH = CMe ₂ B4 A107 Ib-262 T2 H H H - OCH ₂ CH = CMe ₂ B4 A37 Ib-263 T2 H H H - OCH ₂ CH = CMe ₂ B4 A108 Ib-264 T2 H H H - OCH ₂ CH = CMe ₂ B4 A109 Ib-265 T2 H H H - OCH ₂ CH = CMe ₂ B4 AllO Ib-266 T2 H H H - OCH ₂ CH = CMe ₂ B4 A113 Ib-267 T2 H H H - OCH ₂ CH = CMe ₂ B4 A114 Ib-268 T2 H H Me - OCH ₂ CH = CMe ₂ B4 A67 Ib-269 T2 H Me H - OCH ₂ CH = CMe ₂ B4 A67 Ib-270 T2 Me H H - OCH ₂ CH = CMe ₂ B4 A67 Ib-271 T2 H Me H - OCH ₂ CH = CMe ₂ B4 A64 Ib-272 T2 Me H H - OCH ₂ CH = CMe ₂ B4 A64 Ib-273 T2 H H Me - OCH ₂ CH = CMe ₂ B4 A46 Ib-274 T2 H Me H - OCH ₂ CH = CMe ₂ B4 A46 Ib-275 T2 Me H H - OCH ₂ CH = CMe ₂ B4 A46 Ib-276 T2 H H Me - OCH ₂ CH = CMe ₂ B4 A42 Ib-277 T2 H Me H - OCH ₂ CH = CMe ₂ B4 A42 Ib-278 T2 Me H H - OCH ₂ CH = CMe ₂ B4 A42 Ib-279 T2 H H H - OCH ₂ CH ₂ F B4 A46 Ib-280 T2 H H H - and ₂ c = ch B4 A47 Ib-281 T2 H H H - and ₂ ch = ch ₂ B4 A45 Ib-282 T2 H H H - CH ₂ CH ₂ CH = CMe ₂ B4 A67 Ib-283 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A37 Ib-284 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A5 Ib-285 T2 H H H - nh ₂ B4 A37 Ib-286 T2 H H H - nh ₂ B4 A5 Ib-287 T2 H H H - NH-cHex B4 A5 Ib-288 T2 H H H - OCH ₂ -2-furyl B4 A67

• · • ·

4 »· · · · β« ·

Table 74 • ····· 4 4 β * · * * 4 4 9 4 9 4 9 4 9

49993 94 · 4 · 49

169

No. EN} - _w 3_v R12 R13 R ¹⁴ Ris X'-Y ' (B) AND Ib-289 T2 H H H - CH 2 C = CMe B4 A67 Ib-290 T2 H H H - 1-pyrrolyl B4 A67 Ib-291 T2 H H H - 1-pyrrolidinyl B4 A67 Ib-292 T2 H H H - H B4 A5 Ib-293 T2 H H H - About me B4 A46 Ib-294 T2 H no ₂ H - About me B4 A46 Ib-295 T2 H H H - OBn B4 A37 Ib-296 T2 H H H - About me B4 A37 Ib-297 T2 H H H - OCH ₂ CH = CMe ₂ B7 A42 Ib-298 T2 H H H - OCH ₂ CH = CMe ₂ B7 A46 Ib-299 T2 H H H - OCH ₂ CH = CMe ₂ B7 A44 Ib-300 T2 H H H - About me B7 A37 Ib-301 T2 H H H - NHCH ₂ CH = CMe ₂ B7 A37 Ib-302 T2 H H H - NH-i-Pr B7 A37 Ib-303 T2 H H H - NHCH ₂ -cHex B7 A37 Ib-304 T2 H H H - NHCH ₂ -3-Pyr B7 A37 Ib-305 T2 H H H - NH-i-Pent B7 A37 Ib-306 T2 H H H - NH-i-Bu B7 A37 Ib-307 T2 H H H - NHCH ₂ -2-thienyl B7 A37 Ib-308 T2 H H H - NHCH ₂ -3-thienyl B7 A37 Ib-309 T2 H H H - NHCH ₂ -2-furyl B7 A37 Ib-310 T2 H H H - NHCH ₂ -3-furyl B7 A37 Ib-311 T2 H H H - NHCH ₂ -2-Py B7 A37 Ib-312 T2 H H H - nh ₂ B7 A37 Ib-313 T2 H H H - NHCH ₂ CH = CMe ₂ B7 A42 Ib-314 T2 H H H - NHCH ₂ CH = CMe ₂ B7 A46 Ib-315 T2 H H H - SCH ₂ CH = CMe ₂ B7 A42 Ib-316 T2 H H H - SCH ₂ CH = CMe ₂ B7 A46 Ib-317 T2 H H H - SCH ₂ CH = CMe ₂ B7 Alll Ib-318 T2 H H Me - NHCH ₂ CH = CMe ₂ B7 A46 Ib-319 T2 H Me H - NHCH ₂ CH = CMe ₂ B7 A46 Ib-320 T2 Me H H - NHCH ₂ CH = CMe ₂ B7 A46 Ib-321 T2 H H H - NHCH ₂ CH = CMe ₂ B7 A112 Ib-322 T2 H H H - NHCH ₂ CH = CMe ₂ B8 A37

• * * · · · · · · · · · ·

170

Table 75 • · · · · · ·

No. QZ w ³ - ^ R12 R13 R14 R ¹⁵ X'-Y ' (B) AND Ib-323 T2 H H H - OCH ₂ CH = CMe ₂ B8 A42 Ib-324 T2 H H H - OCH ₂ CH = CMe ₂ B8 A46 Ib-325 T2 H H H - OCH ₂ CH = CMe ₂ B8 A51 Ib-326 T2 H H H - OCH ₂ CH = CMe ₂ B8 A52 Ib-327 T2 H H H - OCH ₂ CH = CMe ₂ B8 A89 Ib-328 T2 H H H - OCH ₂ CH = CMe ₂ B8 A54 Ib-329 T2 H H H - OCH ₂ CH = CMe ₂ BIO A42 Ib-330 T2 H H H - OCH ₂ CH = CMe ₂ BIO A46 Ib-331 T2 H H H - OCH ₂ CH = CMe ₂ BIO A44 Ib-332 T2 H H H - OCH ₂ CH = CMe ₂ BIO A48 Ib-333 T2 H H H - OCH ₂ CH = CMe ₂ BIO A54 Ib-334 T2 H H H - OCH ₂ CH = CMe ₂ BIO A117 Ib-335 T2 H H H - OCH ₂ CH = CMe ₂ BIO A5O Ib-336 T2 H H H - OCH ₂ CH = CMe ₂ BIO A115 Ib-337 T2 H H H - OCH ₂ CH = CMe ₂ BIO A116 Ib-338 T2 H H H - OCH ₂ CH = CMe ₂ BIO A89 Ib-339 T2 H H H - OCH ₂ CH = CHMe BIO A46 Ib-340 T2 H H H - OCH ₂ CH ₂ CH = CH ₂ BIO A46 Ib-341 T2 H H H - CH ₂ CH = CHEt BIO A46 Ib-342 T2 H H H - OCH ₂ Cl 2 CMe BIO A46 Ib-343 T2 H H H - OCH ₂ -2-furyl BIO A46 Ib-344 T2 H H H - OCH ₂ -2-furyl BIO A42 Ib-345 T2 H H H - OCH ₂ CH ₂ F BIO A46 Ib-346 T2 H H .H - och ₂ cf ₃ BIO A46 Ib-347 T2 H H H - OCH ₂ -2-furyl BIO A117 Ib-348 T2 H H H - OCH ₂ C = CMe BIO A117 Ib-349 T2 H H H - SMe BIO A46 Ib-350 T2 H H H - SO ₂ Me BIO A46 Ib-351 T2 H H H - OCH ₂ CH = CMe ₂ B12 A42 Ib-352 T2 H H H - OCH ₂ CH = CMe ₂ B12 A46 Ib-353 T2 H H H - OCH ₂ CH = CMe ₂ B12 A58 Ib-354 T2 H H H - OCH ₂ CH = CMe ₂ B12 A48 Ib-355 T2 H H Me - OCH ₂ CH = CMe ₂ B12 A46 Ib-356 T2 H Me H - OCH ₂ CH = CMe ₂ B12 A46 Ib-357 T2 Me H H - OCH ₂ CH = CMe ₂ B12 A46

• · ········ · · · · ····

171

Table 76 · V

No. w ³ - ' R12 R13 R ¹⁴ Ris X'-Y ' (B) AND Ib-358 T2 H H H - SMe B12 A46 Ib-359 T2 H H H - NHCH ₂ CH = CMe ₂ B12 A46 Ib-360 T2 H H H - NH2 B12 A78 Ib-361 T2 H H H - NHCH ₂ CH = CMe ₂ B12 A78 Ib-362 T2 H H H - NH-cHex B12 A37 Ib-363 T2 H H H - OCH ₂ CH = CMe ₂ B13 A46 Ib-364 T2 H H H - OCH ₂ CH = CMe ₂ B13 A50 Ib-365 T2 H H H - OCH ₂ CH = CMe ₂ B17 A46 Ib-366 T2 H H H - OCH ₂ CH = CMe ₂ B17 A44 Ib-367 T2 H H H - OCH ₂ CH = CMe ₂ B17 A50 Ib-368 T2 H H H - OCH ₂ CH = CMe ₂ B17 A94 Ib-369 T2 H H H - OCH ₂ CH = CMe ₂ B17 A86 Ib-370 T2 H H H - OCH ₂ -2-furyl B17 A46 Ib-371 T2 H H H - OCH ₂ -2-furyl B17 A44 Ib-372 T2 H H H - OCH ₂ -2-furyl B17 A94 Ib-373 T2 H H H - OCH ₂ CH = CMe ₂ B23 A46 Ib-374 T2 H H H - OCH ₂ -2-furyl B23 A46 Ib-375 T2 H H H - OCH ₂ CH = CMe ₂ B28 A46 Ib-376 T2 H H H - OCH ₂ CH = CMe ₂ B28 A50 Ib-377 T2 H H H - OCH ₂ CH = CMe ₂ B29 A104 Ib-378 T2 H H H - OCH ₂ CH = CMe ₂ B29 A105 Ib-379 T2 H H H - OCH ₂ CH = CMe ₂ B29 A67 Ib-380 T2 H H H - OCH ₂ CH = CMe ₂ B29 A106 Ib-381 T2 H H H - OCH ₂ CH = CMe ₂ B30 A46 Ib-382 T2 H H H - OCH ₂ -2-furyl B30 A46 Ib-383 T2 H H H - OCH ₂ C = CMe B30 A46 Ib-384 T4 H Cl - H - B4 A37 Ib-385 T4 H About me - H - B4 A37 Ib-386 T4 H NMe ₂ - H - B4 A37 Ib-387 T5 H - H - H B4 A5 Ib-388 T5 H - H - H B4 A37 Ib-389 T5 H - H - nh ₂ B4 A5 Ib-390 T5 H - H - nh ₂ B4 A37 Ib-391 T5 H - H - NHCH ₂ CH = CMe ₂ B4 A5 Ib-392 T5 H - H - NHCH ₂ CH = CMe ₂ B4 A37 Ib-393 T5 H - H - NHCH ₂ CH = CMe ₂ B4 A42 Ib-394 T5 H - H - NHCH ₂ CH = CMe ₂ B4 A46

• 9

172

Table ΊΊ

No. w ³ - ' R12 R13 Rl ' R15 X'-Y ' (B) AND Ib-395 T5 H - H - NHCH ₂ CH = CMe ₂ B4 A118 Ib-396 T5 H - H - OCH ₂ CH = CMe ₂ B4 A67 Ib-397 T5 H - H - OCH ₂ CH = CMe ₂ B7 A46 Ib-398 T5 H - H - NHCH ₂ CH = CMe ₂ B7 A37 Ib-399 T5 H - H - nh ₂ B7 A37 Ib-400 T5 H - H - NHCH ₂ CH = CMe ₂ B12 A37 Ib-401 T6 - H - H H B4 A5 Ib-402 T6 - H - H H B4 A37 Ib-403 T7 H H - - OCH ₂ CH = CMe ₂ B4 A46 Ib-404 T7 H H - - Cl B4 A5 Ib-405 T7 H H - - About me B4 A5 Ib-406 T7 H H - - NMe ₂ B4 A5 Ib-407 T7 H H - - Cl B4 A37 Ib-408 T7 H H - - About me B4 A37 Ib-409 T7 H H - - NMe ₂ B4 A37 Ib-410 T7 H H - - nh ₂ B4 A5 Ib-411 T7 H H - - nh ₂ B4 A37 Ib-412 T7 H H - - NHCH ₂ CH = CMe ₂ B4 A5 Ib-413 T7 H H - - NHCH ₂ CH = CMe ₂ B4 A37 Ib-414 T7 H H - - NHCH ₂ CH = CMe ₂ B4 A42 Ib-415 T7 H H - - NHCH ₂ CH = CMe ₂ B4 A46 Ib-416 T7 H H - - NHCH ₂ CH = CMe ₂ B4 A118 Ib-417 T7 H H - - nh ₂ B7 A37 Ib-418 T7 H H - - NHCH ₂ CH = CMe ₂ B7 A37 Ib-419 T7 H H - - OCH ₂ CH = CMe ₂ B7 A46 Ib-420 T7 H H - NHCH ₂ CH = CMe ₂ B12 A37 Ib-421 T8 H - H H B4 A5 Ib-422 T8 H - - H H B4 A37 Ib-423 T8 H - - H nh ₂ B4 A5 Ib-424 T8 H - - H nh ₂ B4 A37 Ib-425 T8 H - - H NH-cHex B4 A5 Ib-426 T8 H - - H NH-cHex B4 A37 Ib-427 T8 H - - H NHCH ₂ CH = CMe ₂ B4 A5 Ib-428 T8 H - - H NHCH ₂ CH = CMe ₂ B4 A37 Ib-429 T8 H - - H NHCH ₂ CH = CMe ₂ B4 A46 Ib-430 T8 H - - H NHCH ₂ CH = CMe ₂ B4 A118 Ib-431 T8 H - - H OCH ₂ CH = CMe ₂ B7 A46 Ib-432 T8 H - - H nh ₂ B7 A37

173 • titi ·· titititi ·· titi • · ti ti ti ti ti tiititi ··· ··· · ti ti ti · ti ti · ti · ti tititi ti · ti ti ti ti·· ti

Table 78

No. (ty- w ³ - ' R ¹² R ¹³ Ri " Ris X’-Y ' (B) AND Ib-433 T8 H - - H NHCH ₂ CH = CMe ₂ B7 A37 Ib-434 T8 H - - H NHCH ₂ CH = CMe ₂ B7 A42 Ib-435 T8 H - - H NHCH ₂ CH = CMe ₂ B7 A46 Ib-436 T8 H - - H NHCH ₂ CH = CMe ₂ B12 A37 Ib-437 T12 H H H - - B4 A64 Ib-438 T12 H H H - - B4 A80 Ib-439 T12 H H H - - B4 A81 Ib-44O T12 H H H - - B4 A67 Ib-441 T12 H H H - - B7 A37 Ib-442 T13 H H - - - B7 A37 Ib-443 T14 - H H - - B7 A37 Ib-444 T2 H H H - OCH ₂ CH = CMe ₂ B6 A46 Ib-445 T2 H H H - OCH ₂ CH = CMe ₂ Bil A46 Ib-446 T2 H H H - OCH ₂ CH = CMe ₂ B14 A46 Ib-447 T2 H H H - OCH ₂ CH = CMe ₂ B15 A46 Ib-448 T2 H H H - OCH ₂ CH = CMe ₂ B16 A46 Ib-449 T2 H H H - OCH ₂ CH = CMe ₂ B18 A46 Ib-45O T2 H H H - OCH ₂ CH = CMe ₂ B19 A46 Ib-451 T2 H H H - OCH ₂ CH = CMe ₂ B20 A46 Ib-452 T2 H H H - OCH ₂ CH = CMe ₂ B21 A46 Ib-453 T2 H H H - OCH ₂ CH = CMe ₂ B22 A46 Ib-454 T2 H H H - OCH ₂ CH = CMe ₂ B23 A46 Ib-455 T2 H H H - OCH ₂ CH = CMe ₂ B24 A46 Ib-456 T2 H H H - OCH ₂ CH = CMe ₂ B25 A46 Ib-457 T2 H H H - OCH ₂ CH = CMe ₂ B26 A46 Ib-458 T2 H H H - OCH ₂ CH = CMe ₂ B27 A46 Ib-459 T2 H H H - OCH ₂ CH = CMe ₂ B28 A46 Ib-460 T2 H H H - OCH ₂ CH = CMe ₂ B29 A46 Ib-461 T2 H H H - OCH ₂ CH = CMe ₂ B30 A46 Ib-462 T2 H H H - OCH ₂ CH = CMe ₂ B31 A46 Ib-463 T2 H H H - OCH ₂ CH = CMe ₂ B32 A46 Ib-464 T2 H H H - OCH ₂ CH = CMe ₂ B33 A46 Ib-465 T2 H H H - OCH ₂ CH = CMe ₂ B34 A46 Ib-466 T2 H H H - OCH ₂ CH = CMe ₂ B35 A46 Ib-467 T2 H H H - OCH ₂ CH = CMe ₂ B36 A46 Ib-468 T2 H H H - OCH ₂ CH = CMe ₂ B37 A46 Ib-469 T2 H H H - OCH ₂ CH = CMe ₂ B38 A46

• · · · · · · · · · · · · · · · · · · · · · ·

174 · ·······························

Table 79

No. <4 w ³ ^ R12 R13 R14 Ri 5 X’-Y ’ (B) AND Ib-470 T2 H H H - OCH ₂ CH = CMe ₂ B39 A46 Ib-471 T2 H H H - OCH ₂ CH = CMe ₂ B40 A46 Ib-472 T2 H H H - OCH ₂ CH = CMe ₂ B41 A46 Ib-473 T2 H H H - OCH ₂ CH = CMe ₂ B42 A46 Ib-474 T2 H H H - OCH ₂ CH = CMe ₂ B43 A46 Ib-475 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A2 Ib-476 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A3 Ib-477 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A4 Ib-478 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A7 Ib-479 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A9 Ib-480 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A10 Ib-481 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A12 Ib-482 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A13 Ib-483 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A14 Ib-484 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A15 Ib-485 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A16 Ib-486 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A17 Ib-487 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A18 Ib-488 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A19 Ib-489 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A20 Ib-490 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A21 Ib-491 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A22 Ib-492 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A23 Ib-493 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A24 Ib-494 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A25 Ib-495 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A26 Ib-496 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A27 Ib-497 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A28 Ib-498 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A29 Ib-499 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A30 Ib-500 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A31 Ib-501 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A34 Ib-502 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A36 Ib-503 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A39 Ib-504 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A40 Ib-505 T2 H H H - OCH ₂ CH = CMe ₂ B4 A56 Ib-506 T2 H H H - OCH ₂ CH = CMe ₂ B4 A70 Ib-507 T2 H H H - OCH ₂ CH = CMe ₂ B4 A87 Ib-508 T2 H H H - OCH ₂ CH = CMe ₂ B4 A88 Ib-509 T2 H H H - OCH ₂ CH = CMe ₂ B4 A89

175

0 00 0000 • 0 0

000 «0 0 0 • 0 0 0 0 •• 0 00 00 0

Table 80

No. 77 w ³ - ⁷ R12 R13 Ri " R15 X'-Y ’ (B) AND Ib-510 T2 H H H - OCH ₂ CH = CMe ₂ B4 A90 Ib-511 T2 H H H - OCH ₂ CH = CMe ₂ B4 A91 Ib-512 T2 H H H - OCH ₂ CH = CMe ₂ B4 A92 Ib-513 T2 H H H - OCH ₂ CH = CMe ₂ B4 A93 Ib-514 T2 H H H - OCH ₂ CH = CMe ₂ B4 A94 Ib-515 T2 H H H - OCH ₂ CH = CMe ₂ B4 A95 Ib-516 T2 H H H - OCH ₂ CH = CMe ₂ B4 A96 Ib-517 T2 H H H - OCH ₂ CH = CMe ₂ B4 A97 Ib-518 T2 H H H - OCH ₂ CH = CMe ₂ B4 A98 Ib-519 T2 H H H - OCH ₂ CH = CMe ₂ B4 A99 Ib-520 T2 H H H - OCH ₂ CH = CMe ₂ B4 A100 Ib-521 T2 H H H - OCH ₂ CH = CMe ₂ B4 A101 Ib-522 T2 H H H - OCH ₂ CH = CMe ₂ B4 A102 Ib-523 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A103 Ib-524 T2 H H H - OCH ₂ CH = CMe ₂ B4 A104 Ib-525 T2 H H H - OCH ₂ CH = CMe ₂ B4 A105 Ib-526 T2 H H H - OCH ₂ CH = CMe ₂ B4 A106 Ib-527 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A107 Ib-528 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A108 Ib-529 T2 H H H - NHCH ₂ CH = CMe ₂ B4 A109 Ib-530 T2 H H H - NHCH ₂ CH = CMe ₂ B4 AllO Ib-531 T2 H H H - OCH ₂ CH = CMe ₂ B4 Alll Ib-532 T2 H H H - OCH ₂ CH = CMe ₂ B4 A112 Ib-533 T2 H H H - OCH ₂ CH = CMe ₂ B4 A113 Ib-534 T2 H H H - OCH ₂ CH = CMe ₂ B4 A114 Ib-535 T2 H H H - OCH ₂ CH = CMe ₂ B4 A115 Ib-536 T2 H H H - OCH ₂ CH = CMe ₂ B4 A116 Ib-537 T2 H H H - OCH ₂ CH = CMe ₂ B4 A117 Ib-538 T2 H H H - OCH ₂ CH = CMe ₂ B4 A118 lb-539 T2 H H H - OCH ₂ CH = CMe ₂ B4 A119 lb-540 T2 H H H - OCH ₂ CH = CMe ₂ B4 A120 lb-541 T2 H H H - OCH ₂ CH = CMe ₂ B4 A121 Ib-542 T2 H H H - OCH ₂ CH = CMe ₂ B4 A122 Ib-543 T2 H H H - OCH ₂ CH = CMe ₂ B4 A123 Ib-544 T2 H H H - OCH ₂ CH = CMe ₂ B4 A124 Ib-545 T2 H H H - OCH ₂ CH = CMe ₂ B4 A125 Ib-546 T2 H H H - OCH ₂ CH = CMe ₂ B4 A126

φφ φφ φ * φ · φ · φ φ

176

Φφ »····· • φφφ φ · φ

Table 81

No. w ³ - ' R12 R1 ³ R ¹⁴ Ris X'-Y ' (B) AND Ib-547 T2 H H H - OCH ₂ CH = CMe ₂ B4 A127 Ib-548 T2 H H H - OCH ₂ CH = CMe ₂ Bl A120 Ib-549 T2 H H H - OCH ₂ CH = CMe ₂ Bl A122 Ib-550 T2 H H H - OCH ₂ CH = CMe ₂ Bl A124 Ib-551 T2 H H H - OCH ₂ CH = CMe ₂ Bl A126 Ib-552 T2 H H H - OCH ₂ -2-furyl BIO A128 Ib-553 T2 H H H - OCH ₂ -2-furyl BIO A129 Ib-554 T2 H H H - OCH ₂ -2-furyl BIO A130 Ib-555 T2 H H H - OCH ₂ -2-furyl BIO A131 Ib-556 T2 H H H - _N 2 CH ₂ CH = CMe ₂ ^with COOCH ₂ OCO (CH 2) ₂ COOH B12 A132 Ib-557 T2 H H H - _x CH ₂ CH = CMe ₂ N _x ^{2 2} COOCH (Me) OCOMe B12 A133 Ib-558 T2 H H H - XH ₂ CH = CMe ₂ —N _with COOCH ₂ OCO (CH ₂ ) ₁₄ Me B12 A134 Ib-559 T2 H H H - , CH ₂ CH = CMe ₂ —N _in CH ₂ NHCO-CrH ₄ -o-OCH ₂ OCOMe B12 A135 Ib-560 T5 H - H - OCH ₂ CH = CMe ₂ B4 A121 Ib-561 T5 H - H - OCH ₂ CH = CMe ₂ B4 A123 Ib-562 T5 H - H - OCH ₂ CH = CMe ₂ B4 A125 Ib-563 T5 H - H - OCH ₂ CH = CMe ₂ B4 A127 Ib-564 T2 H H H - OCH ₂ CH = CMe ₂ B4 A136 Ib-565 T2 H H H - OCH ₂ CH = CMe ₂ B4 A137 Ib-566 T2 H H H - OCH ₂ CH = CMe ₂ B4 A138 Ib-567 T2 H H H - OCH ₂ CH = CMe ₂ B4 A139 Ib-568 T2 H H H - OCH ₂ CH = CMe ₂ B4 A140 Ib-569 T2 H H H - OCH ₂ CH = CMe ₂ B4 A141 Ib-570 T2 H H H - OCH ₂ CH = CMe ₂ B4 A142 Ib-571 T2 H H H - OCH ₂ CH = CMe ₂ B4 A143 Ib-572 T2 H H H - ^ CH ₂ CH = CMe ₂ - < ^{2 2} COOCH ₂ OCOCH ₂ OH B12 A78 Ib-573 T2 H H H - _N CH ₂ CH = CMe ₂ ^x COOCH ₂ OCO (CH ₂ ) ₂ COOH B12 A78 Ib-574 T2 H H H - ^ CH ₂ CH = CMe ₂ —N _x COOCH ₂ OCOMe B12 A78 Ib-575 T2 H H H - _N CH ₂ CH = CMe ₂ ^S COOCH (M e) OCOCM e ₃ B12 A78

177 • fc fcfc fcfc ·· fcfc fcfc • fc · · fc fcfcfcfc • fcfcfc · fcfcfcfc · * · fcfc fcfc fcfc fcfc · · fcfcfc fcfcfcfc ·· · · · ···

Table 82

Ic '

No. V2 C (B) AND Ic-1 0 C2 B4 A32 Ic-2 0 C2 B4 A35 Ic-3 0 C3 B4 A6 Ic-4 0 C3 B4 A8 Ic-5 0 C3 B4 All Ic-6 0 C3 B4 A33 Ic-7 0 C3 B4 A35 Ic-8 0 C5 B4 All Ic-9 0 C5 B4 A35 Ic-10 0 C6 Bl A35 Ic-11 0 C6 Bl A37 Ic-12 0 C6 B4 All Ic-13 0 C6 B4 A32 Ic-14 0 C6 B4 A35 Ic-15 0 C19 B4 A35 Ic-16 0 C25 B4 A41 Ic-17 0 C26 B4 A41 Ic-18 0 C27 B4 A41 Ic-19 0 C28 B4 A41 Ic-20 0 C29 B4 A41 Ic-21 NH C2 B4 A32 Ic-22 NH C2 B4 A35 Ic-23 OCHž C2 B4 A32 Ic-24 OCH ₂ C2 B4 A33

9 9 9 9 9

9 9 9 9 9

999 99 99 99 99 9 9

999 99 99 9 99 ··

178

Table 83

Table 84

No. V ² C (B) AND Ic-25 OCH ₂ C2 B4 A35 Ic-26 och ₂ C6 B4 A35 Ic-27 och ₂ C19 B4 A35 Ic-28 ch ₂ o C2 Bl A32 Ic-29 ch ₂ o C2 Bl A35 Ic-30 ch ₂ o C2 B4 A35 Ic-31 ch ₂ o C3 Bl A33 Ic-32 ch ₂ o C3 B4 A33 Ic-33 nhch ₂ C2 B4 A35 Ic-34 nhch ₂ C6 B4 A35 Ic-35 CH = CH C2 B4 A32 Ic-36 CH = CH C2 B4 A33 Ic-37 CH = CH C2 B4 A35 Ic-38 CH = CH C3 B4 A33 Ic-39 CH = CH C6 B4 A32 Ic-40 CH = CH C6 B4 A35 Ic-41 CH = CH C19 B4 A35 Ic-42 C ^ C C2 B4 A32 Ic-43 C-C C2 B4 A35 Ic-44 C ^ C C3 B4 A35 Ic-45 OC C19 B4 A35 Ic-46 WHAT C2 B4 A32 Ic-47 WHAT C2 B4 A35 Ic-48 CH (OH) C2 B4 A32 Ic-49 CH (OH) C2 B4 A35

No. V ² C - <b \ - W ^2-7 R ⁸ R ⁹ Rio AND Ie-1 0 C6 SI H H H A6 Ie-2 0 C6 SI H H H A8 Ie-3 0 C6 SI H H H A32 Ie-4 0 C9 SI H H H A6 Ie-5 0 C9 SI H H H A8 Ie-6 0 C9 SI H H H A14 Ie-7 0 C9 SI H H H A17 Ie-8 0 C9 SI H H H A32 Ie-9 0 C9 SI H H H A33 Ie-10 0 C6 SI H Me Me A32

• «φ φ φ φ • • φ Φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ

179

Table 85

Νο. V ² C —6b \ - vj ² - ' R8 R ⁹ Ri ° AND Ie-11 0 C6 Sl H Me Me A35 Ie-12 0 Cl S3 Me - About me A6 Ie-13 0 Cl S3 Me - About me A8 Ie-14 0 Cl S3 Me - About me A14 Ie-15 0 Cl S3 Me - About me A17 Ie-16 0 Cl S3 Me - About me A32 Ie-17 0 C4 S3 Me - About me A8 Ie-18 0 C4 S3 Me - About me A14 Ie-19 0 C4 S3 Me - About me A17 Ie-20 0 C4 S3 Me - About me A32 Ie-21 0 C4 S3 Me - About me A33 Ie-22 0 C9 S3 Me - About me A6 Ie-23 0 C9 S3 Me - About me A8 Ie-24 0 C9 S3 Me - About me A32 Ie-25 0 C9 S3 Me - About me A33 Ie-26 NH Cl S3 Me - About me A6 Ie-27 NH Cl S3 Me - About me A8 Ie-28 NH Cl S3 Me - About me A14 Ie-29 NH Cl S3 Me - About me A17 Ie-30 NH Cl S3 Me - About me A32 Ie-31 NH C4 S3 Me - About me A8 Ie-32 NH C4 S3 Me About me A14 Ie-33 NH C4 S3 Me - About me A17 Ie-34 NH C4 S3 Me - About me A32 Ie-35 NH C4 S3 Me - About me A33 Ie-36 NH C9 S3 Me - About me A6 Ie-37 NH C9 S3 Me - About me A8 Ie-38 NH C9 S3 Me - About me A14 Ie-39 NH C9 S3 Me - About me A17 Ie-40 NH C9 S3 Me - About me A32 Ie-41 NH C9 S3 Me - About me A33

180 ·· ftft ftftftft ftft ftft · ftft · ftftftft ftft ftft ftftftft ftft ftft ftft ftft ftft

Table 86

If

No. (c) - W ³ -? w ² - ⁷ R ⁸ R ⁹ Rio AND If-1 morpholino si H H H A6 If-2 morpholino SI H H H A8 If-3 morpholino SI H H H A32 If-4 morpholino SI H H H A33 If-5 morpholino SI H Me Me A6 If-6 morpholino Sl H Me Me A8 If-7 morpholino si H Me Me A32 If-8 morpholino Sl H Me Me A33 If-9 morpholino S3 Me - About me A6 If-10 morpholino S3 Me - About me A8 If-11 morpholino S3 Me - About me A32 If-12 morpholino S3 Me - About me A33 If-13 4-Me-piperazinyl S3 Me - About me A6 If-14 4-Me-piperazinyl S3 Me - About me A8 If-15 4-Me-piperazinyl S3 Me - About me A32 If-16 4-Me-piperazinyl S3 Me - About me A33 If-17 4-Ph-piperazinyl S3 Me - About me A6 If-18 4-Ph-piperazinyl S3 Me - About me A8 If-19 4-Ph-piperazinyl S3 Me - About me A32 If-20 4-Ph-piperazinyl S3 Me - About me A33 If-21 1-imidazolyl S3 Me - About me A6 If-22 1-imidazolyl S3 Me - About me A8 If-23 1-imidazolyl S3 Me - About me A32 If-24 1-imidazolyl S3 Me - About me A33 If-25 1-triazolyl S3 Me - About me A6 If-26 1-triazolyl S3 Me - About me A8 If-27 1-triazolyl S3 Me - About me A32 If-28 1-triazolyl S3 Me - About me A33 If-29 2-prenyloxypyridin- 5-yl Sl H Me Me A46 If-30 2-prenyloxypyridin- 5-yl Sl H Me Me A42

9 9 9 9

9 «

9 · 9 9

9

998 9 9 9

9 9 9 • 99 9 · 99 * 9 9

9

9

9

99 99

181

Table 87

> <

182

I 4 · 4 * · 4 ·· ··

Table 88

No. mp, 1 H-NMR Ia-2 195-197 ° C, 1 H-NMR (CDCl 3 -DMSO-d 6) δ 1.77 (3H, s), 1.82 (3H, s), 4.63 (2H, J = 6.8), 5.52 (1H, br t, J = 6.8) 6. 25 (1H, s), 6.93-6.98 (3H, m), 7.10 (1 H, dd, J = 2.2, 8.3), 7.20 (1 H, d, J = 2.2), 7.69 (1 H, d, J = 8.1), 7.85 (1 H, dd, J = 2.0, 8.1), 7.89 (2 H, d, J = 8.8), 8.53 (1 H, br s), 8.82 (1 H, d, J = 2.0) Ia-4 181-182 ° C, δ-NMR (CDCl 3) δ 3.18 (3H, s), 5.19 (2H, s), 5.78 (1H, s), 7.04 (1H, d, J = 8.3), 7.12 (1H δ d, J = 2.2, 8.3), 7.25 (lH, d, J = 2.2), 7.38-7.45 (7H, m), 7.76 (lH, br d, J = 8.3), 7.92 (lH, dd, J = 2.4, 8.3), 8.88 (1 H, br d, J = 2.4) Ia-5 171-172 ° C, δ-NMR (CDCl 3) δ 3.40 (3H, s), 3.43 (3H, s), 5.29 (2H, s), 7.36-7.53 (8H, m), 7.78-7.81 (2H, m) 8.21 (1 H, d, J = 8.3), 8.21 (1 H, dd, J = 2.2, 8.3), 8.25 (2 H, d, J = 8.8), 9.02 (1 H, br s) Ia-6 165-166 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.82 (3H, s), 3.18 (3H, s), 3.25 (3H, s), 4.65 (2H, d, J = 6.8) 7.53 (1H, dd, J = 2.2, 8.5), 7.50 (1H, d, J = 6.8), 7.13 (1H, d, J = 8.5), 7.58 (1H, d, J = 2.2, 8.5), 7.58 (1H, d, J = 2.2), 7.77 (1H, dd, J = 0.7, 8.3), 7.92 (1H, dd, J = 2.2, 8.3), 8.10 (2H, d, J = 8.8), 8.88 (1H , dd, J = 0.7 Ia-8 176-177 ° C, δ-NMR (CDCl 3) δ 3.87 (3H, s), 5.18 (2H, s), 5.77 (1H, s), 7.01 (2H, d, J = 9.0), 7.02 (1H, d) J = 8.6), 7.11 (1H, dd, J = 2.2, 8.6), 7.24 (1H, d, J = 2.2), 7.40-7.45 (5H, m), 7.71 (1H, dd, J = 1.0, 8.3) ), 7.86 (1 H, dd, J = 2.4, 8.3), 7.99 (2 H, d, J = 9.0), 8.84 (1 H, dd, J = 1.0, 2.4) Ia-9 187-188 ° C, 1 H-NMR (CDCl 3) δ 3.13 (3H, s), 3.88 (3H, s), 5.19 (2 H, s), 7.02 (2 H, d, J = 8.8), 7.17 (1 H, d, J = 8.6), 7.37-7.49 (5H, m), 7.51 (1 H, dd, J = 2.2, 8.6), 7.59 (1 H, d, J = 2.2), 7.73 (1 H, br d, J = 8.3) 7.86 (1H, dd, J = 2.4, 8.3), 8.00 (2H, d, J = 8.8), 8.83 (1 H, br d, J = 2.4) Ia-10 141-142 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.82 (3H, s), 3.88 (3H, s), 4.63 (2H, d, J = 6.8), 5.52 (1H, s); br t, J = 6.8), 5.79 (1 H, s), 6.97 (1 H, d, J = 8.3), 7.02 (2 H, d, J = 9.0), 7.11 (1 H, dd, J = 2.2, 8.3), 7.21 (1H, d, J = 2.2), 7.71 (1H, dd, J = 0.7, 8.3), 7.86 (1H, dd, J = 2.4, 8.3), 7.99 (2H, d, J = 9.0), 8.85 ( 1H, dd, J = 0.7 Ia-11 161-162 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.82 (3H, s), 3.24 (3H, s), 3.88 (3H, s), 4.65 (2H, d, J = 6.8), 5.50 (1 H, br t, J = 6.8), 7.02 (2 H, d, J = 9.0), 7.11 (1 H, d, J = 8.5), 7.52 (1 H, dd, J = 2.4, 8.5), 7.57 (1H, d, J = 2.4), 7.73 (1H, dd, J = 0.7, 8.3), 7.86 (1H, dd, J = 2.4, 8.3), 8.00 (2H, d, J = 9.0), 8.83 ( 1H, dd, J = 0.7 Ia-12 233-236 ° C, δ-NMR (CDCl 3) δ 3.13 (3H, s), 3.14 (3H, s), 5.20 (2H, s), 5.21 (2H, s), 7.17 (2H, dd, J = 1.7) 8.39, 7.36-7.54 (11H, m), 7.59 (1 H, d, J = 2.4), 7.73 (1 H, d, J = 8.3), 7.78 (1 H, dd, J = 2.4, 8.3), 7.98- 8.02 (2H, m); 8.84 (1 H, d, J = 2.5) Ia-13 150-151 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.82 (6H, s), 4.63 (4H, d, J = 6.8), 5.52 (2H, brt, J = 6.8) 5.73 (1H, s), 5.78 (1H, d), 6.97 (2H, d, J = 8.3), 7.10 (1H, dd, J = 2.2, 8.3), 7.21 (1H, d, J = 2.2), 7.57 (1 H, dd, J = 2.2, 8.3), 7.60 (1 H, d, J = 2.2), 7.69 (1 H, br d, J = 8.3), 7.85 (1 H, dd, J = 2.4, 8.3), 8.84 (1 H, br d, J = 2.4) la-15 172-173 ° C, Ή-NMR (CDCl 3) δ 5.11 (1H, s), 5.17 (2H, s), 5.75 (1H, s), 6.93 (2H, d, J = 8.5), 6.95-7.03 (2H) (m), 7.11 (1H, d, J = 2.0), 7.38-7.45 (5H, m), 7.62 (1H, d, J = 8.1), 7.67 (1H, d, J = 8.1), 7.96 (2H, d, J = 8.5)

• 0 · * 00 · · 0 · · 0

0 «0 0 0 0 * 00

00 0 0000 «00« 0 00 00 «0 0 0 000« «« <

• 00 00 00 00 00

183

Table 89

Ia-16 159-161 ° C, δ-NMR (CDCl 3) δ 1.77 (3H, s), 1.83 (3H, s), 4.63 (2H, d, J = 6.8), 5.02 (1 H, s), 5.52 (1h, br t, J = 6.8, 5.75 (1H, s), 6.92 (2H, d, J = 8.5), 6.94 (1H, d, J = 8.3), 6.97 (1H, dd, J = 2.2, 8.3), 7.08 (1H, d, J = 2.2), 7.62 (1H, d, J = 8.1), 7.66 (1H, d, J = 8.1), 7.95 (2H, d, J = 8.5); Ia-17 134-134.5 ° C, Ή-NMR (CDCl 3) δ 3.13 (3H, s), 3.18 (3H, s), 5.20 (2H, s), 7.16 (1 H, d, J = 8.5), 7.37-7.50 (9H) , m), 7.71 and 7.74 (each 1H, ABq, J = 8.1), 8.10 (2H, d, J = 8.8) Ia-18 99-100 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.82 (3H, s), 3.19 (3H, s), 3.24 (3H, s), 4.66 (2H, d, J = 6.8) ), 5.51 (1H, br t, J = 6.8), 7.10 (1H, d, J = 8.5), 7.38-7.48 (4H, m), 7.71 and 7.74 (each 1H, ABq, J = 8.1), 8.10 ( 2H, d, J = 8.8) Ia-21 215-216 ° C, δ-NMR (CDCl 3 -DMSO-d 5) δ 1.77 (3H, s), 1.82 (3H, s), 2.35 (3H, s), 4.63 (2H, d, J = 6.8), 5.54 (1H, br t, J = 6.8), 6.51 (1 H, s), 6.79 (1 H, dd, J = 2.2, 8.1), 6.93-6.96 (4 H, m), 7.52 (1 H, s), 7.87 (2 H) d, J = 8.8), 8.43 (1 H, s), 8.79 (1 H, s) Ia-22 203-204 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.80 (3H, s), 2.37 (3H, s), 3.89 (3H, s), 4.64 (2H, d, J = 6.8) 5.56 (1H, br, J = 6.8), 6.20 (1H, br s), 6.86-6.89 (2H, m), 6.89 (2H, d, J = 8.8), 6.97 (1H, d, J = 8.5), 7.55 (1 H, s), 7.88 (2 H, d, J = 8.8), 8.48 (1 H, s) Ia-23 140-141 ° C, Ή-NMR (CDCl 3) δ 2.39 (3H, s), 3.17 (3H, s), 5.18 (2H, s), 5.78 (1H, s), 6.83 (1H, dd, J = 2.2) 8.33, 6.98 (1H, d, J = 2.2), 7.03 (1H, d, J = 8.3), 7.40 (2H, d, J = 8.8), 7.41-7.47 (5H, m), 7.59 (1H, s), 8.07 (2 H, d, J = 8.8), 8.50 (1 H, s) Ia-24 156-157 ° C, Ή-NMR (CDCl 3) δ 2.39 (3H, s), 3.13 (3H, s), 3.18 (3H, s), 5.20 (2H, s), 7.18 (1H, d, J = 8.5) 7.26 (1H, dd, J = 2.0, 8.5), 7.36-7.49 (8H, m), 7.61 (1 H, s), 8.07 (2 H, d, J = 90), 8.50 (1 H, s) Ia-25 111-112 ° C, 1 H-NMR (CDCl 3) δ 1.78 (3H, s), 1.83 (3H, s), 2.39 (3H, s), 3.18 (3H, s), 3.24 (3H, s), 4.65 ( 2H, d, J = 6.8, 5.51 (1H, brt, J = 6.8), 7.11 (1H, d, J = 8.5), 7.26 (1H, dd, J = 2.2, 8.5), 7.34 (1H, d) J = 2.2), 7.40 (2H, d, J = 8.8), 7.60 (1 H, s), 8.07 (2 H, d, J = 8.8), 8.50 (1 H, s) Ia-26 124-127 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.80 (3H, s), 2.39 (3H, s), 3.18 (3H, s), 3.90 (3H, s), 4.65 ( 2H, d, J = 6.8. 5.57 (1H, br t, J = 6.8), 6.87-6.91 (2H, m), 6.98 (1H, d, J = 8.3), 7.40 (2H, d, J = 8.8) ), 7.60 (1 H, s), 8.08 (2 H, d, J = 8.8), 8.53 (1 H, s) Ia-27 213-214 ° C, δ-NMR (CDCl 3) δ 2.58 (3H, s), 5.21 (2H, s), 5.87 (1H, s), 7.06-7.18 (5H, m), 7.42-7.49 (7H, m) 8.29 (1 H, brs), 8.86 (1 H, brs), 9.01 (1 H, brs) Ia-28 198-199 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.82 (3H, s), 2.42 (3H, s), 4.63 (2H, d, J = 6.7), 5.51 (1H, t) J = 6.7, 5.68 (1H, s), 5.77 (1H, s), 6.87 (2H, d, J = 7.8), 6.96 (1H, d, J = 8.5), 7.10 (1H, dd, J = 8.5, 2.4), 7.21 (1H, d, J = 2.4), 7.44 (2H, d, J = 7.8), 7.71 (1H, d, J = 2.4), 8.68 (1H, d, J = 2.4), Ia-31 198-199 ° C, Ή-NMR (CDCl 3) δ 2.53 (3H, s), 3.14 (3H, s), 3.21 (3H, s), 5.21 (2H, s), 7.22 (1H, d, J = 8.5) 7.39-7.49 (7H, m), 7.55-7.62 (2 H, -m), 7.73 (2 H, d, J = 9.2), 8.05 (1 H, brs), 8.84 (1 H, brs) Ia-32 142-144 ° C, 1 H-NMR (CDCl 3) δ 1.78 (3H, s), 1.82 (3H, s), 2.43 (3H, s), 3.17 (3H, s), 3.24 (3H, s), 4.65 ( 2H, d, J = 6.7, 5.50 (1H, brt, J = 6.7), 7.12 (1H, d, J = 8.5), 7.40 (2H, dd, J = 6.7, 1.8), 7.52 (1H, dd) J = 8.6, 2.4), 7.57 (1H, s), 7.64 (2H, d, J = 8.5), 7.74 (1H, s), 8.70 (1H, d, J = 2.5)

184 • ·· • 0 · * 0 4 ·· * ♦ · 00

9 ·

9 «

e · · · · · 0 44 • 9 9

4 <·

4 4

4 · 40

Table 90

Ia-35 152-154 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.83 (3H, s), 2.59 (3H, s), 4.12 (2H, d, J = 7.3), 5.53 (1H, t) J = 7.3), 5.77 (1 H, brs), 6.79-6.95 (5H, m), 7.49 (1 H, d, J = 8.0), 7.55 (1 H, d, J = 8.0), 7.88 (2 H, d, J = 8.5) Ia-38 109-112 ° C, Ή-NMR (CDCl 3) δ 2.60 (3H, s), 3.12 (3H, s), 3.16 (3H, s), 5.19 (2H, s), 7.15 (1H, d, J = 8.5) 7.27 (1H, dd, J = 7.8, 1.8), 7.35-7.50 (8H, m), 7.59 (2 H, s), 8.09 (2 H, d, J = 9.2) Ia-39 oil, 1.78 (3H, s), 1 H-NMR (CDCl 3) δ 1.82 (3H, s), 2.60 (3H, s), 3.17 (3H, s), 3.24 (3H, s), 4.65 (2H, d, J = 6.7), 5.51 (1 H, br t, J = 6.7), 7.09 (1 H, d, J = 8.6), 7.24-7.27 (1 H, m), 7.34-7.35 (2 H, m), 7.40 (1 H, d, J = 8.6) 7.59 (2 H, s), 8.09 (2 H, d, J = 9.2) Ia-42 175-176 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.83 (3H, s), 2.32 (3H, s), 2.54 (3H, s), 4.63 (2H, d, J = 6.8) 5.52 (1H, brs), 5.53 (1H, t, J = 6.8), 5.75 (1H, brs), 6.80-6.84 (3H, m), 6.93 (1 H, d, J = 7.8), 6.95 (1 H) , d, J = 1.8), 7.387 .41 (3H, m) Ia-43 177-178 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.79 (3H, s), 2.32 (3H, s), 2.56 (3H, s), 3.90 (3H, s), 4.64 ( 2H, d, J = 6.8), 5.56 (1H, t, J = 6.8), 6.75 (2H, d, J = 8.5), 6.87-6.97 (3H, m), 7.33 (2H, d, J = 8.5) 7.43 (1 H, s) Ia-45 79-81 ° C, Ή-NMR (CDCl 3) δ 2.33 (3H, s), 2.53 (3H, s), 3.16 (3H, s), 5.18 (2H, s), 5.75 (1H, s), 6.83 ( 1 H, dd, J = 7.8, 1.8), 6.98 (1 H, d, J = 1.8), 7.00 (1 H, d, J = 8.5), 7.37-7.55 (8H, m), 7.63 (2 H, d, J = 8.5) Ia-46 163-164 ° C, δ-NMR (CDCl 3) δ 2.34 (3H, s), 2.54 (3H, s), 3.13 (3H, s), 3.17 (3H, s), 5.19 (2H, s), 7.15 ( 1 H, d, J = 8.5), 7.27 (1 H, dd, J = 8.5, 2.5), 7.35-7.50 (9H, m), 7.62 (2 H, d, J = 8.5) Ia-47 oil, δ-NMR (CDCl 3) δ 1.77 (3H, s), 1.82 (3H, s), 2.34 (3H, s), 2.54 (3H, s), 3.17 (3H, s), 3.23 (3H, s) 4.66 (2H, d, J = 7.3), 5.51 (1 H, br t, J = 7.3), 7.08 (1 H, d, J = 8.6), 7.26 (1 H, dd, J = 8.6, 2.4), 7.35 ( 1H, d, J = 2.4., 7.39 (2H, d, J = 8.6), 7.43 (1H, s), 7.64 (2H, d, J = 8.6). Ia-48 149-150 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.80 (3H, s), 2.35 (3H, s), 2.54 (3H, s), 3.17 (3H, s), 3.90 ( 3H, s), 4.64 (2 H, d, J = 6.8), 5.57 (1 H, t, J = 6.8), 6.87 (1 H, s), 6.88-6.98 (2 H, m), 7.39 (2 H, d, J = 8.5), 7.44 (1 H, s), 7.63 (2 H, d, J = 8.5) Ia-65 237-239 ° C, δ-NMR (CDCl 3 -CD 3 OD) δ 3.16 (3H, s), 5.21 (2H, s), 6.96 (2H, d, J = 8.6), 7.20 (1H, d, J = 9.3) 7.38-7.51 (5H, m), 7.72 (1H, br d, J = 8.3), 7.90-7.95 (3H, m), 8.80 (1H, br d, J = 2.4) Ia-66 152-153 ° C, δ-NMR (CDCl 3) δ 1.76 (3H, s), 1.81 (3H, s), 4.63 (2H, d, J = 6.8), 5.51 (1 H, br t, J = 6.8), 5.59 (1H, br, s), 5.75 (1H, s), 6.95 (2H, d, J = 8.6), 6.97 (1H, d, J = 8.3), 7.50 (2H, d, J = 8.6), 7.56 ( 1H, dd, J = 2.2, 8.3), 7.59 (1H, d, J = 2.2), 7.69 (1H, dd, J = 0.7, 8.3), 7.86 (1H, 2.4, 8.3), 8.83 (1H, dd, J = 0.7, 2.4) Ia-68 167-168 ° C, δ-NMR (CDCl 3) δ 3.13 (3H, s), 3.20 (3H, s), 5.21 (2H, s), 7.18 (1 H, d, J = 8.3), 7.38-7.48 (7H) (m), 7.67 (2H, d, J = 8.8), 7.76 (1H, br d, J = 8.3), 7.91 (1H, dd, J = 2.4, 8.3), 7.99-8.03 (2H, m), 8.85 (1 H, br d, J = 2.4) Ia-69 151-152.5 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.81 (3H, s), 3.20 (3H, s), 3.24 (3H, s), 4.66 (2H, d, J = 6.8) ), 5.50 (1H, br t, J = 6.8), 7.12 (1H, d, J = 9.3), 7.42 (2H, d, J = 8.5), 7.67 (2H, d, J = 8.5), 7.76 (1H) br br, J = 8.3), 7.90 (lH, dd, J = 2.4, 8.3), 8.00-8.03 (lH, m), 8.85 (lH, br d, J = 2.4) Ia-71 220-221 ° C Ή-NMR (CDCl 3) δ 2.57 (3H, s), 3.51 (2H, brs), 5.18 (2H, s), 7.14 (1 H, d, J = 7.3), 7.15-7.62 (11H, m), 8.11 (1 H, d, J = 1.8), 8.78 (1 H, d, J = 1.8)

9

4 4 • 4

9

185

Table 91

Ia-73 180-181 ° C, 1 H-NMR (CDCl 3) δ 1.74 (3H, s), 1.79 (3H, s), 2.42 (3H, s), 4.61 (2H, d, J = 6.8), 5.50 (1H, t) J = 6.8, 6.84-6.96 (5H, m), 7.05 (1 H, dd, J = 7.8, 1.8), 7.14 (1 H, d, J = 1.8), 7.44 (2 H, d, J = 9.2), 7.71 (1H, d, J = 1.8); 8.65 (1H, d, J = 1.8); Ia-75 164-165 ° C, 1 H-NMR (CDCl 3) δ 2.53 (3H, s), 3.13 (3H, s), 3.21 (3H, s), 5.19 (2H, s), 7.16 (1H, d, J = 7.3) 7.32-7.50 (7H, m), 7.61 (2H, dd, J = 8.5, 2.4), 7.70 (2H, d, J = 7.3), 7.79 (1 H, d, J = 1.8) 8.76 (1 H, d) , J = 1.8) Ia-76 151-152 ° C 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.81 (3H, s), 2.48 (3H, s), 3.20 (3H, s), 3.21 (3H, s), 4.65 (2H) δ, J = 6.8, 5.50 (1H, t, J = 6.8), 7.11 (1H, d, J = 7.9), 7.41 (2H, d, J = 9.2), 7.55 (1H, dd, J = 7.8) 1.8 (7.5) (1H, s), 7.66 (2H, d, J = 7.9), 7.74 (1H, d, J = 1.8), 8.71 (1H, d, J = 1.8), Ia-79 189-191 ° C, 1 H-NMR (CDCl 3) δ 2.34 (3H, s), 5.18 (2H, s), 5.29 (1H, br s), 5.71 (1H, s), 6.83 (1H, dd, J = 2.2, 8.3), 6.93 (2H, d, J = 8.6), 7.03 (1 H, d, J = 8.3), 7.23 (2 H, d, J = 8.6), 7.37-7.47 (5H, m), 7.54 (1 H) (s), 7.55 (1H, dd, J = 2.2, 8.3), 7.60 (2H, d, J = 2.2), 8.45 (1H, s); Ia-80 165-166 ° C, @ 1 H-NMR (CDCl3) .delta. 1.76 (3H, s), 1.81 (3H, s), 2.35 (3H, s), 4.63 (2H, d, J = 6.8), 5.51 (1H, br) t, J = 6.8, 5.75 (1H, s), 6.19 (1H, br s), 6.92 (2H, d, J = 8.8), 6.96 (1H, d, J = 8.8), 7.21 (2H, d, J = 8.8), 7.52-7.57 (3 H, m), 8.44 (1 H, s) Ia-82 189-190 ° C, Ή-NMR (CDCl 3) δ 2.35 (3H, s), 3.13 (3H, s), 3.22 (3H, s), 5.20 (2H, s), 7.18 (1H, d, J = 9.0) 7.36-7.49 (9H, m), 7.58 (1 H, s), 7.99-8.02 (2 H, m), 8.46 (1 H, s) Ia-83 169-170 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.81 (3H, s), 2.35 (3H, s), 3.22 (3H, s), 3.24 (3H, s), 4.66 ( 2H, d, J = 6.8, 5.50 (1H, brt, J = 6.8), 7.11 (1H, d, J = 8.6), 7.40 (4H, s), 7.58 (1H, s), 7.96 (1H, d, J = 2.2), 8.00 (1 H, dd, J = 2.2, 8.6), 8.45 (1 H, s) Ia-85 143-146 ° C, Ή-NMR (CDCl 3) δ 2.53 (3H, s), 5.03 (1H, brs), 5.18 (2H, s), 5.72 (1H, s), 6.92 (2H, dd, J = 7.8) 1.02, 7.02 (1 H, d, J = 6.8), 7.23 (2 H, dd, J = 7.3, 1.8), 7.33-7.48 (5 H, m), 7.49-7.60 (3 H, m), 7.67 (1 H, d, J = 1.8) Ia-87 168-169 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.81 (3H, s), 2.56 (3H, s), 4.63 (2H, d, J = 6.8), 4.84 (1H, s) 5.51 (1 H, t, J = 6.8), 5.70 (1 H, s), 6.91 (2 H, d, J = 8.5), 6.95 (1 H, d, J = 8.5), 7.22 (2 H, s), 7.51 (2H, s), 7.55 (1 H, dd, J = 8.5, 2.4), 7.62 (1 H, d, J = 2.4) Ia-89 174-175 ° C, Ή-NMR (CDCl 3) δ 2.56 (3H, s), 3.13 (3H, s), 3.21 (3H, s), 5.20 (2H, s), 7.15 (1H, d, J = 8.5) 7.29-7.48 (9H, m), 7.56 (2H, s), 7.99 (1 H, dd, J = 8.5, 2.4), 8.03 (1 H, d, J = 2.4) Ia-90 141-142 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.81 (3H, s), 2.56 (3H, s), 3.21 (3H, s), 3.24 (3H, s), 4.65 ( 2H, d, J = 6.8. 5.50 (1H, t, J = 6.8); 7.10 (1H, d, J = 8.6); 7.36-7.43 (4H, m); 7.55 (2H, d, J = 1.2); 7.98 (1H, dd, J = 8.6 and 2.4), 8.01 (1H, d, J = 1.2) Ia-93 118-121 ° C, Ή-NMR (CDCl 3) δ 2.36 (3H, s), 2.51 (3H, s), 3.10 (3H, s), 5.10 (1 H, brs), 5.18 (2 H, s), 6.90 ( 2H, d, J = 8.6., 7.14 (1H, d, J = 8.6); 7.21-7.48 (8H, m); 7.52 (1H, dd, J = 8.6, 1.8); 1.8) Ia-94 168-169 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.81 (3H, s), 2.33 (3H, s), 2.51 (3H, s), 4.61 (2H, d, J = 6.8) 5.31 (1H, brs), 5.51 (1 H, t, J = 6.8), 5.73 (1 H, s), 6.87-6.95 (3 H, m), 7.04 (1 H, dd, J = 8.5, 1.8), 7.14 (1H, d, J = 1.8), 7.21-7.24 (2 H, ra), 7.37 (1 H, s) Ia-96 140-141 ° C, Ή-NMR (CDCl 3) δ 2.38 (3H, s), 2.50 (3H, s), 3.11 (3H, s), 3.21 (3H, s), 5.19 (2H, s), 7.16 ( 1 H, d, J = 8.5, 7.33-7.51 (10H, m), 7.55 (1 H, dd, J = 7.8, 1.8), 7.62 (1 H, d, J = 1.8)

· · · · · · · · · · · · · · · · · · · · · · · · · ·

186

Table 9

Ia-97 106-107 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.81 (3H, s), 2.38 (3H, s), 2.51 (3H, s), 3.20 (3H, s), 3.21 ( 3H, s), 4.64 (2H, d, J = 6.8), 5.49 (1H, t, J = 6.8), 7.10 (1H, d, J = 8.0), 7.35-7.44 (5H, m), 7.51-7.65 (2H, m) Ia-125 121-122 ° C, δ-NMR (CDCl 3) δ 2.38 (3H, s), 3.90 (3H, s), 4.03 (3H, s), 5.21 (2H, s), 6.77 (1H, dd, J = 2.0) 8.32, 6.82 (1H, d, J = 2.0), 6.97 (1H, d, J = 8.3), 7.32-7.49 (8H, m), 8.46-8.49 (2H, m) Ia-127 110-111 ° C, δ-NMR (CDCl 3) δ 2.39 (3H, s), 4.03 (3H, s), 5.11 (2H, s), 7.06 (2H, d, J = 8.5), 7.22 (2H, d) J = 8.5), 7.34-7.51 (8H, m), 8.44-8.50 (2 H, m) Ia-128 115-116 ° C, δ-NMR (CDCl 3) δ 2.38 (3H, s), 4.03 (3H, s), 5.07 (2H, s), 7.06 (2H, d, J = 9.2), 7.21 (4H, d) J = 9.2), 7.36 (2H, d, J = 8.5), 7.45-7.51 (3 H, m), 8.46-8.50 (2H, m) Ia-129 129-130 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.82 (3H, s), 2.39 (3H, s), 4.03 (3H, s), 4.56 (2H, d, J = 6.7) 5.55 (1H, br t, J = 6.7), 7.00 (2H, d, J = 8.5), 7.21 (2H, d, J = 8.5), 7.46-7.51 (3H, m) and 8.46-8.50 (2H). , m) Ia-131 121-122 ° C, δ-NMR (CDCl 3) δ 2.39 (3H, s), 4.03 (3H, s), 5.16 (2H, s), 5.75 (1H, s), 6.76 (1H, dd, J = 2.2) 8.33, 6.90 (1 H, d, J = 2.2), 7.01 (1 H, d, J = 8.1), 7.38-7.5 (8H, m), 8.46-8.50 (2 H, m) Ia-132 142-143 ° C, Ή-NMR (CDCl 3) δ 2.29 (3H, s), 2.41 (3H, s), 4.02 (3H, s), 5.14 (2H, s), 7.02 (1H, d, J = 1.2) 7.05-7.11 (2H, m), 7.33-7.49 (8H, m), 8.458.50 (2H, m) Ia-133 161.5-162.5 ° C, δ-NMR (CDCl 3) δ 2.42 (3H, s), 3.11 (3H, s), 4.03 (3H, s), 5.18 (2H, s), 7.14 (1H, d, J = 8.6) 7.21 (1H, dd, J = 2.0, 8.6), 7.31- (1H, d, J = 2.0), 7.37-7.50 (8H, m), 8.46-8.49 (2H, m) Ia-134 142-143 ° C, δ-NMR (CDCl 3) δ 2.39 (3H, s), 4.03 (3H, s), 5.23 (2H, s), 7.15 (1 H, d, J = 8.5), 7.17-7.25 (2 H) , m), 7.33-7.51 (8H, m), 8.45-8.50 (2 H, m) Ia-135 132-133 ° C, Ή-NMR (CDCl 3) δ 2.37 (3H, s), 4.03 (3H, s), 4.94 (2H, s), 6.98 (1 H, d, J = 8.6), 7.15 (1 H, dd) J = 1.8, 8.6), 7.17 (1H, d, J = 1.8), 7.33-7.60 (11H, m), 7.87 (2H, d, J = 7.3), 8.45-8.59 (2H, m) Ia-136 127-128 ° C, Ή-NMR (CDCl 3) δ 2.40 (3H, s), 2.42 (3H, s), 4.04 (3H, s), 5.14 (2H, s), 5.70 (1H, s), 6.79 ( 1H, dd, J = 1.8, 7.9), 6.90 (1H, d, J = 1.8), 7.05 (1H, d, J = 7.9), 7.22-7.36 (3H, m), 7.40 (1H, d, J 6.7), 7.43-7.55 (3 H, m), 8.44-8.50 (2H, m) Ia-137 87-89 ° C, Ή-NMR (CDCl 3) δ 2.39 (3H, s), 2.41 (3H, s), 4.03 (3H, s), 5.12 (2H, s), 5.73 (1H, s), 6.76 ( 1H, dd, J = 1.8, 7.9), 6.90 (1H, d, J = 1.8), 7.01 (1H, d, J = 7.9), 7.18-7.36 (4H, m), 7.43-7.53 (3H, m) 8.46-8.52 (2 H, m) Ia-138 114-115 ° C, δ-NMR (CDCl 3) δ 2.39 (6H, s), 4.02 (3H, s), 5.10 (2H, s), 5.74 (1H, s), 6.75 (1H, dd, J = 2.0) 8.39, 6.89 (1H, d, J = 2.0), 7.01 (1H, d, J = 8.3), 7.24 (2H, d, J = 8.6), 7.36 (2H, d, J = 8.6), 7.45- 7.50 (3H, m), 8.468.50 (2 H, m) Ia-139 192-193 ° C, Ή-NMR (CDCl 3) δ 2.42 (3H, s), 2.43 (3H, s), 3.06 (3H, s), 4.04 (3H, s), 5.16 (2H, s), 7.15- 7.33 (6H, m); 7.41-7.50 (4H, m); 8.46-8.51 (2 H, m) Ia-140 151-152 ° C, Ή-NMR (CDCl 3) δ 2.39 (3H, s), 2.42 (3H, s), 3.12 (3H, s), 4.03 (3H, s), 5.14 (2H, s), 7.14 ( 1 H, d, J = 8.5), 7.18-7.31 (6 H, m), 7.46-7.50 (3 H, m), 8.45-8.50 (2H, m) Ia-141 188-189 ° C, Ή-NMR (CDCl 3) δ 2.39 (3H, s), 2.41 (3H, s), 3.11 (3H, s), 4.03 (3H, s), 5.13 (2H, s), 7.14 ( 1H, d, J = 8.6, 7.20 (1H, dd, J = 2.2, 8.6), 7.22 (2H, d, J = 8.0), 7.30 (1H, d, J = 2.2), 7.36 (2H, d, J = 8.0), 7.47-7.50 (3 H, m), 8.46-8.49 (2H, m)

• ·

187 · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · ·

Table 93

Ia-142 166-167 ° C, Ή-NMR (CDCl 3) δ 2.39 (3H, s), 3.91 (3H, s), 4.03 (3H, s), 5.15 (2H, s), 6.18 (1H, s), 6.75 ( 1H, dd, J = 1.8, 7.9), 6.89 (1H, d, J = 2.4), 6.97 (1H, d, J = 7.9), 7.03 (1H, d, J = 7.9), 7.34-7.49 (5H, m), 8.46-8.50 (2 H, m) Ia-143 166-167 ° C, Ή-NMR (CDCl 3) δ 2.39 (3H, s), 3.84 (3H, s), 4.03 (3H, s), 5.13 (2H, s), 5.74 (1H, s), 6.75 ( 1 H, dd, J = 1.8, 8.5), 6.89 (1 H, d, J = 1.8), 6.90-7.05 (4H, m), 7.34 (1 H, d, J = 7.9), 7.44-7.50 (3H, m) 8.45-8.50 (2H, m) Ia-144 125-126 ° C, δ-NMR (CDCl 3) δ 2.39 (3H, s), 3.85 (3H, s), 4.03 (3H, s), 5.08 (2H, s), 5.70 (1H, s), 6.76 ( 1H, dd, J = 1.8, 7.9), 6.89 (1H, d, J = 8.5), 6.96 (2H, d, J = 8.5), 7.02 (1H, d, J = 7.9), 7.38 (2H, d, J = 8.5), 7.44-7.50 (3 H, m), 8.45-8.50 (2H, m) Ia-145 193-195 ° C, Ή-NMR (CDCl 3) δ 2.42 (3H, s), 3.13 (3H, s), 3.87 (3H, s), 4.03 (3H, s), 5.21 (2H, s), 6.94 ( 1 H, d, J = 7.9), 6.98-7.04 (1 H, m), 7.19-7.21 (2 H, m), 7.30 (1 H, d, J = 1.8), 7.36 (1 H, d, J = 7.9) 7.45- 7.50 (4H, m); 8.45-8.50 (2 H, m) Ia-146 166-167 ° C, Ή-NMR (CDCl 3) δ 2.41 (3H, s), 3.15 (3H, s), 3.84 (3H, s), 4.03 (3H, s), 5.16 (2H, s), 6.91 ( 1 H, d, J = 8.5, 7.02-7.06 (2 H, m), 7.12 (1 H, d, J = 8.5), 7.20 (1 H, dd, J = 1.8, 8.5), 7.30 (1 H, d, J = 1.8), 7.35 (1 H, d, J = 7.9) 7.45-7.49 (3 H, m), 8.45-8.50 (2 H, m) Ia-147 171-172 ° C Ή-NMR (CDCl 3) δ 2.41 (3H, s), 3.09 (3H, s), 3.84 (3H, s), 4.03 (3H, s), 5.10 (2H, s), 6.94 (2H) δ, J = 8.5), 6.97-7.23 (2 H, m), 7.29 (1 H, d, J = 1.8), 7.39 (2 H, d, J = 8.5), 7.45-7.49 (3 H, m), 8.45- 8.49 (2H, m) Ia-148 177-179 ° C, δ-NMR (CDCl 3) δ 2.39 (3H, s), 4.03 (3H, s), 5.27 (2H, s), 6.72 (1 H, dd, J = 2.4, 8.5), 6.93 (1 H) δ, J = 1.8), 7.12 (1 H, d, J = 7.9), 7.31-7.36 (2 H, m), 7.46-7.49 (3 H, m), 7.78 (1 H, dt, J = 1.8, 7.3), 8.46-8.50 (2 H, m), 8.68 (1 H, d, J = 4.9), 9.76 (1 H, s) Ia-149 221-212 ° C, δ-NMR (CDCl 3) δ 2.39 (3H, s), 4.03 (3H, s), 5.19 (2H, s), 5.69 (1H, s), 6.78 (1H, dd, J = 1.8) 7.91, 6.92 (1H, d, J = 2.4), 7.01 (1H, d, J = 8.5), 7.35-7.40 (1H, m), 7.45-7.51 (3H, m) and 7.80 (1H, d, J = 7.9), 8.46-8.50 (2H, m), 8.65 (1 H, d, J = 4.9), 8.72 (1 H, s) Ia-150 222-224 ° C, Ή-NMR (CDCl 3) δ 2.39 (3H, s), 4.03 (3H, s), 5.19 (2H, s), 6.08 (1H, s), 6.75 (1H, dd, J = 1.8) 6.95 (1H, d, J = 6.7); 6.94 (1H, s); 7.35 (2H, d, J = 6.1); 7.45-7.51 (3H. M); 8.25-8.50 (2H. M) 8.65 (2H, d, J = 5.5%) Ia-151 195-197 ° C, Ή-NMR (CDCl 3) δ 2.41 (3H, s), 3.23 (3H, s), 4.03 (3H, s), 5.32 (2H, s), 7.13 (1H, d, J = 8.5) 7.20 (1H, dd, J = 2.4, 8.5), 7.26-7.33 (2H, m), 7.46-7.50 (3H, m), 7.62 (1 H, d, J = 7.3), 7.78 (1 H, dt, J = 1.8, 7.9), 8.458.50 (2 H, m), 8.62 (1 H, d, J = 4.9) Ia-152 173-174 ° C, Ή-NMR (CDCl 3) δ 2.42 (3H, s), 3.13 (3H, s), 4.03 (3H, s), 5.21 (2H, s), 7.15 (1H, d, J = 7.9) 7.21 (1H, d, J = 1.8), 7.31 (1H, d, J = 1.8), 7.36-7.41 (1H, m), 7.47-7.89 (3H, m), 8.46-8.50 (2H, m) 8.73 (1H, s); 8.75 (1H, d, J = 4.9); 8.73 (1H, s); Ia-153 186-187 ° C, Ή-NMR (CDCl 3) δ 2.41 (3H, s), 3.20 (3H, s), 4.03 (3H, s), 5.22 (2H, s), 7.06 (1H, d, J = 8.5) 7.21 (1H, dd, J = 1.8, 8.5), 7.32 (1H, d, J = 2.4), 7.42 (1H, d, J = 6.1), 7.47-7.50 (3H, m), 8.45-8.50 ( 2H, m), 8.68 (2H, d, J = 4.9) Ia-154 112-113 ° C, δ-NMR (CDCl 3) δ 2.37 (3H, s), 3.16 (2H, t, J = 6.7), 4.02 (3H, s), 4.32 (2H, t, J = 6.7), 5.55 (1H, s), 6.74 (1H, dd, J = 1.8, 8.5), 6.85 (1H, d, J = 1.8), 6.93 (1H, d, J = 8.5), 7.25-7.39 (5H, m), 7.45-7.49 (3 H, m), 8.458.49 (2H, m)

188 · · · · «« «« «« «« «• • • • • • • • • 188 188 188 · ··· · · ··

Table 94

Ia-155 169-170 ° C, Ή-NMR (CDCl 3) δ 2.39 (3H, s), 2.88 (3H, s), 3.18 (2H, t, J = 6.7), 4.02 (3H, s), 4.35 (2H, t) J = 6.7), 7.07 (1 H, d, J = 8.5), 7.19 (1 H, dd, J = 1.8, 7.9), 7.25-7.38 (6 H, m), 7.46-7.49 (3 H, m), 8.44- 8.49 (2H, m) Ia-156 117-119 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.83 (3H, s), 2.39 (3H, s), 4.03 (3H, s), 4.62 (2H, d, J = 6.8) 5.55 (1H, br t, J = 6.8), 5.75 (1H, s), 6.75 (1H, dd, J = 2.2, 8.3), 6.87 (1H, d, J = 2.2), 6.94 (1H, d) J = 8.3, 7.45-7.50 (3H, m), 8.46-8.49 (2 H, m) Ia-157 121-124 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.82 (3H, s), 2.42 (3H, s), 3.23 (3H, s), 3.40 (3H, s), 4.63 ( 2H, d, J = 6.8., 5.51 (1H, br t, J = 6.8), 7.07 (1H, d, J = 8.6), 7.19 (1H, dd, J = 2.0, 8.6), 7.28 (1H, d) J = 2.0), 7.45-7.50 (3H, m), 8.45-8.49 (2 H, m) Ia-159 79-80 ° C, Ή-NMR (CDCl 3) δ 1.75 (3H, s), 1.76 (3H, s), 2.38 (3H, s), 2.54 (2H, q, J = 6.7), 4.03 (3H, s) 4.08 (2H, t, J = 6.7), 5.23 (1H, t, J = 7.3), 5.71 (1H, s), 6.74 (1H, dd, J = 1.8, 7.9), 6.87 (1H, d, J = 1.8), 6.92 (1 H, d, J = 7.9), 7.44-7.51 (3 H, m), 8.45-8.50 (2 H, m) Ia-160 152-153 ° C, 1 H-NMR (CDCl 3) δ 1.69 (3H, s), 1.74 (3H, s), 2.41 (3H, s), 2.56 (2H, q, J = 6.7), 3.21 (3H, s) 4.03 (3H, s), 4.08 (2 H, t, J = 6.7), 5.22 (1 H, t, J = 6.7), 7.06 (1 H, d, J = 7.9), 7.20 (1 H, dd, J = 1.8, 7.9), 7.28 (1 H, d, J = 1.8), 7.46-7.50 (3 H, m), 8.45-8.50 (2H, m) Ia-162 200.5-201.5 ° C, Ή-NMR (CDCl 3) δ 2.38 (3H, s), 3.11 (3H, s), 4.01 (3H, s), 5.17 (2H, s), 5.38 (1H, s), 6.90 ( 2H, d, J = 8.8), 7.13 (1 H, d, J = 8.5), 7.19 (1 H, dd, J = 2.0, 8.5), 7.29 (1 H, d, J = 2.0), 7.37-7.49 (5H, m) 8.37 (2H, d, J = 8.8) Ia-163 163-168 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.83 (3H, s), 2.36 (3H, s), 4.01 (3H, s), 4.62 (2H, d, J = 6.6) 5.53 (1H, br t, J = 6.6), 5.58 (1H, br s), 5.74 (1H, br s), 6.73 (1H, dd, J = 2.0, 8.3), 6.86 (1H, d, J = 2.0), 6.89 (2H, d, J = 8.8), 6.93 (1H, d, J = 8.3), 8.37 (2H, J = 8.8) Ia-167 185.5-186.5 ° C, δ-NMR (CDCl 3) δ 2.41 (3H, s), 3.11 (3H, s), 3.18 (3H, s), 4.02 (3H, s), 5.18 (2H, s), 7.15 ( 1 H, d, J = 8.3), 7.21 (1 H, dd, J = 2.0, 8.3), 7.30 (1 H, d, J = 2.0), 7.36-7.49 (7H, m), 8.54 (2 H, d, J = 8.8) Ia-168 138-139 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.82 (3H, s), 2.41 (3H, s), 3.18 (3H, s), 3.22 (3H, s), 4.02 ( 3H, s), 4.64 (2H, d, J = 6.8), 5.51 (1 H, br t, J = 6.8), 7.08 (1 H, d, J = 8.5), 7.19 (1 H, dd, J = 2.0, 8.5) 7.29 (1H, d, J = 2.0), 7.39 (2H, d, J = 9.0), 8.54 (2H, J = 9.0) Ia-173 202-204 ° C, δ-NMR (CDCl 3) δ 2.40 (3H, s), 2.55 (3H, s), 3.11 (3H, s), 4.02 (3H, s), 5.17 (2H, s), 7.14 ( 1H, d, J = 8.5, 7.20 (1H, dd, J = 2.0, 8.5), 7.30 (1H, d, J = 2.0), 7.33 (2H, br d, J = 8.6), 7.37-7.50 (5H) m, 8.40 (2H, br d, J = 8.6) Ia-175 205-206 ° C, δ-NMR (CDCl 3) δ 2.44 (3H, s), 3.10 (3H, s), 3.12 (3H, s), 4.05 (3H, s), 5.18 (2H, s), 7.16 ( 1 H, d, J = 8.5, 7.21 (1 H, dd, J = 2.0, 8.5), 7.31 (1 H, d, J = 2.0), 7.37-7.50 (5H, m), 8.05 (2 H, br d, J) = 8.6), 8.68 (2H, br d, J = 8.6) Ia-176 178-179 ° C, Ή-NMR (CDCl 3) δ 2.40 (3H, s), 3.11 (3H, s), 4.01 (3H, s), 5.17 (2H, s), 7.12-7.22 (4H, m), 7.29 (1H, d, J = 2.0), 7.37-7.50 (5h, m), 8.48 (2H, dd, J = 5.6, 9.0). Ia-177 127-128 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.83 (3H, s), 2.37 (3H, s), 4.01 (3H, s), 4.62 (2H, d, J = 6.8) 5.54 (1H, br t, J = 6.8), 5.74 (1H, s), 6.74 (1H, dd, J = 2.0, 8.3), 6.86 (1H, d, J = 2.0), 6.94 (1H, d) J = 8.3), 7.14 (2H, d, J = 8.8), 8.48 (2H, dd, J = 5.6, 8.8)

9991 ··

189 · · ♦ • · ♦

Table 95

Ia-178 143-144 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.82 (3H, s), 2.40 (3H, s), 3.23 (3H, s), 4.02 (3H, s), 4.63 ( 2H, d, J = 6.8), 5.51 (1H, brt, J = 6.8), 7.05-7.20 (4H, m), 7.27 (IH, d, J = 2.2), 8.48 (2H, dd, J = 5.6) , 9.0) Ia-179 118-120 ° C, δ-NMR (CDCl 3) δ 2.43 (3H, s), 3.12 (3H, s), 4.05 (3H, s), 5.18 (2H, s), 7.15 (IH, d, J = 8.6) 7.21 (IH, dd, J = 2.0, 8.6), 7.31 (IH, d, J = 2.0), 7.38-7.50 (5H, m), 7.60 (IH, br, J = 7.8), 7.73 (IH) , br d, J = 7.8, 8.67 (IH, br d, J = 7.8), 8.75 (IH, brs) Ia-180 114-115 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.83 (3H, s), 2.40 (3H, s), 4.04 (3H, s), 4.63 (2H, d, J = 6.8) ), 5.53 (IH, br, J = 6.8), 5.74 (IH, d), 6.75 (IH, d, J = 2.0, 8.3), 6.87 (IH, d, J = 2.0), 6.95 (IH, d) J = 8.3), 7.60 (IH, t, J = 7.8), 7.72 (IH, br, J = 7.8), 8.67 (IH, br, J = 7.8), 8.75 (IH, s) Ia-181 102-103 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.82 (3H, s), 2.43 (3H, s), 3.23 (3H, s), 4.05 (3H, s), 4.64 ( 2H, d, J = 6.8, 5.51 (IH, br, J = 6.8), 7.08 (IH, d, J = 8.6), 7.20 (IH, dd, J = 2.2, 8.6), 7.28 (IH, d) J = 2.2), 7.60 (IH, d, J = 7.6), 7.73 (IH, d, J = 7.6), 8.67 (IH, d, J = 7.6), 8.75 (IH, s) Ia-182 155-156 ° C, Ή-NMR (CDCl 3) δ 2.41 (3H, s), 4.06 (3H, s), 5.17 (2H, s), 5.75 (IH, s), 6.76 (IH, dd, J = 2.0) 8.3 (1H, d, J = 2.0), 7.02 (IH, d, J = 8.3), 7.40-7.48 (5H, m), 7.65 (IH, t, J = 8.1), 8.31 (IH, ddd, J = 1.2, 2.5, 8.1), 8.83 (IH, ddd, J = 1.2, 1.5, 8.1), 9.31 (IH, dd, J = 1.5, 2.5) Ia-183 160-167 ° C, δ-NMR (CDCl 3) δ 2.44 (3H, s), 3.12 (3H, s), 4.06 (3H, s), 5.19 (2H, s), 7.16 (1H, d, J = 8.5) 7.22 (1H, dd, J = 2.2, 8.5), 7.31 (1H, d, J = 2.2), 7.38-7.49 (5H, m), 7.65 (1H, t, J = 8.1), 8.32 (IH, ddd, J = 1.2, 2.4, 8.3), 8.83 (IH, ddd, J = 1.2, 1.5, 8.3), 9.31 (IH, ddd, J = 1.5, 2.4) Ia-184 153-155 ° C, 1 H-NMR (CDCl 3) 2.40 (3H, s), 3.11 (3H, s), 4.02 (3H, s), 5.17 (2H, s), 6.81 (1H, ddd, J = 1.2, 2.5, 7.8), 7.14 (IH, d, J = 8.5), 7.20 (IH, d, J = 2.2, 8.5), 7.27 (IH, t, J = 7.8), 7.30 (IH, d, J = 2.2) 7.37-7.48 (5H, m), 7.81 (IH, ddd, J = 1.5, 2.5), 7.88 (IH, ddd, J = 1.2, 1.5, 7.8) Ia-185 143-144 ° C, Ή-NMR (CDCl 3) δ 2.22 (3H, s), 2.40 (3H, s), 3.11 (3H, s), 4.03 (3H, s), 5.17 (2H, s), 7.14 ( IH, d, J = 8.6, 7.21 (IH, dd, J = 2.0, 8.6), 7.30 (IH, d, J = 2.0), 7.31 (IH, s), 7.37-7.48 (6H, m), 7.91 (IH, br, J = 8.1), 8.23 (IH, br, J = 8.1), 8.35 (IH, br s) Ia-186 171-172 ° C, δ-NMR (CDCl 3) δ 2.40 (3H, s), 3.05 (3H, s), 3.12 (3H, s), 4.02 (3H, s), 5.18 (2H, s), 6.59 ( 1H, br s), 7.14 (IH, d, J = 8.6), 7.20 (IH, dd, J = 2.0, 8.6), 7.30 (IH, d, J = 2.0), 7.37-7.52 (7H, m), 8.24 (IH, br s), 8.31 (IH, ard, J = 6.8). Ia-187 165-167 ° C, 1 H-NMR (CDCl 3) 1.77 (3H, s), 1.83 (3H, s), 2.39 (3H, s), 3.05 (3H, s), 4.03 (3H, s), 4.6 (2H , d, J = 6.8, 5.5 (IH, br, J = 6.8), 5.74 (IH, s), 6.45 (IH, br s), 6.73 (IH, dd, J = 2.2, 8.3), 6.86 ( 1 H, d, J = 2.2), 7.45-7.52 (2 H, m), 6.94 (1 H, d, J = 8.3), 8.30-8.34 (1 H, m) Ia-188 150-151 ° C, 1 H-NMR (CDCl 3) δ 1.58 (3H, s), 1.67 (3H, s), 2.41 (3H, s), 2.96 (3H, s), 3.12 (3H, s), 4.03 ( 3H, s), 4.36 (2 H, d, J = 7.3), 5.18 (2 H, s), 5.29 (1 H, br t, J = 7.3), 7.15 (1 H, d, J = 8.6), 7.20 (1 H, s) dd, J = 2.0, 8.6), 7.29 (1H, d, J = 2.0), 7.37-7.48 (7 H, m), 8.42-8.45 (2H, m) Ia-189 91-94 ° C, 1 H-NMR (CDCl 3) 1.58 (3H, s), 1.67 (3H, s), 1.77 (3H, s), 1.83 (3H, s), 2.38 (3H, s), 2.96 (3H) 4.02 (3H, s), 4.36 (2 H, d, J = 6.8), 4.62 (2 H, d, J = 6.8), 5.29 (1 H, br t, J = 6.8), 5.52 (1 H, br) t, J = 6.8, 5.76 (IH, s), 6.73 (IH, d, J = 2.2, 8.3), 6.86 (IH, d, J = 2.2), 6.94 (IH, d, J = 8.3), 7.45 -7.51 (2 H, m), 8.42-8.46 (2 H, m)

• ΦΦ ·· φφφφ ·· · φφφ · · · ···

190 • φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ

Table 96

Ia-190 110-111 ° C, 1 H-NMR (CDCl 3) δ 1.58 (3H, s), 1.67 (3H, s), 1.77 (3H, s), 1.82 (3H, s), 2.41 (3H, s), 2.97 ( 3H, s), 3.23 (3H, s), 4.02 (3H, s), 4.36 (2 H, d, J = 7.1), 4.64 (2 H, d, J = 7.1), 5.29 (1 H, br t, J = 7.1), 5.51 (1 H, br t, J = 7.1), 7.08 (1 H, d, J = 8.5), 7.19 (1 H, dd, J = 2.0, 8.5), 7.27 (1 H, d, J = 2.0), 7.46-7.52 (2 H, m), 8.43 (2 H, m) Ia-191 131-132 [deg.] C Ia-192 171.5-172 ° C, Ή-NMR (CDCl 3) δ 2.40 (3H, s), 3.11 (3H, s), 3.89 (3H, s), 5.18 (2H, s), 7.15 (1 H, d, J = 8.6) 7.22 (1H, dd, J = 2.0, 8.6), 7.30 (1H, d, J = 2.0), 7.38-7.50 (5H, m), 7.56 (1H, ddd, J = 1.5, 7.6, 7.6), 7.66 (1 H, ddd, J = 1.5, 7.6, 7.6), 7.73 (1 H, dd, J = 1.5, 7.6), 8.17 (1 H, dd, J = 1.5, 7.6) Ia-194 249-251 ° C, Ή-NMR (CDCl 3) δ 2.27 (3H, s), 2.45 (3H, s), 3.12 (3H, s), 4.05 (3H, s), 5.30 (2H, s), 7.13- 7.24 (3H, m), 7.31 (1H, d, J = 2.0), 7.38-7.50 (6H, m), 8.62 (1H, dd, J = 1.7, 8.3), 8.73 (1H, br d, J = 8.1) ), 13.18 (1 H, br s) Ia-195 180-181 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.83 (3H, s), 2.27 (3H, s), 2.42 (3H, s), 4.04 (3H, s), 4.63 ( 2H, d, J = 6.8, 5.53 (1H, br t, J = 6.8), 5.77 (1H, s), 6.76 (1H, dd, J = 2.0, 8.3), 6.88 (1H, d, J = 2.0) 6.96 (1H, d, J = 8.3), 7.16 (1H, ddd, J = 1.2, 7.0, 8.1), 7.46 (1H, ddd, J = 1.7, 7.0, 8.5), 8.63 (1H, dd, J) = 1.7, 8.1), 8.73 (1 H, br d, J = 8.5), 13.28 (1 H, br s) Ia-196 169-170 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.82 (3H, s), 2.27 (3H, s), 2.45 (3H, s), 3.23 (3H, s), 4.04 ( 3H, s), 4.65 (2H, d, J = 6.8), 5.52 (1 H, br t, J = 6.8), 7.16 (1 H, ddd, J = 1.2, 7.3, 8.1), 7.22 (1 H, dd, J) = 2.2, 8.6), 7.29 (1 H, d, J = 2.2), 7.47 (1 H, ddd, J = 1.5, 7.3, 8.1), 8.62 (1 H, dd, J = 1.5, 8.1), 8.73 (1H, br d, J = 8.1., 13.21 (1 H, br s) Ia-197 176-178 ° C, Ή-NMR (CDCl 3) δ 2.45 (3H, s), 3.03 (3H, s), 3.12 (3H, s), 4.05 (3H, s), 5.18 (2H, s), 7.14- 7.24 (3H, m), 7.30 (1 H, d, J = 2.0), 7.38-7.51 (6H, m), 7.76 (1 H, dd, J = 1.0, 8.3), 8.69 (1 H, dd, J = 1.7, 8.1), 13.19 (1H, s) Ia-199 157-158 ° C, δ-NMR (CDCl 3) δ 1.36 (3H, t, J = 6.7), 2.42 (3H, s), 3.11 (3H, s), 4.54 (2H, q, J = 6.7), 5.18 (2H, s), 7.14 (1 H, d, J = 7.9), 7.21 (1 H, dd, J = 1.8, 8.5), 7.32 (1 H, d, J = 2.4), 7.37-7.49 (8H, m), 8.43-8.48 (2 H, m) Ia-200 122-123 ° C, Ή-NMR (CDCl 3) δ 1.36 (3H, t, J = 7.3), 2.39 (3H, s), 2.40 (3H, s), 4.54 (2H, q, J = 7.3), 5.11 (2H, s), 5.69 (1 H, s), 6.76 (1 H, dd, J = 1.8, 8.5), 6.89 (1 H, d, J = 1.8), 7.00 (1 H, d, J = 8.5), 7.22- 7.50 (3H, m); 8.428.48 (2 H, m) Ia-201 147-148 ° C, Ή-NMR (CDCl 3) δ 1.36 (3H, t, J = 6.7), 2.39 (3H, s), 2.42 (3H, s), 3.10 (3H, s), 4.54 (2H, q) J = 6.7), 7.13 (2H, d), 7.14 (1H, d, J = 8.5), 7.18-7.28 (3H, m), 7.31 (1H, d, J = 1.8), 7.36 (2H, d, J = 8.5), 7.46-7.50 (3 H, m), 8.43-8.48 (2H, m) Ia-202 99-100 ° C, 1 H-NMR (CDCl 3) δ 1.36 (3H, s), 1.77 (3H, s), 1.83 (3H, s), 2.39 (3H, s), 4.54 (2H, q, J = 7.3) ), 4.62 (2H, d, J = 6.7), 5.53 (1 H, br t, J = 6.7), 5.72 (1 H, s), 6.75 (1 H, dd, J = 2.4, 8.5), 6.87 (1 H, d) J = 2.4), 6.93 (1 H, d, J = 8.5), 7.42-7.52 (3 H, m), 8.42-8.50 (2 H, m) Ia-203 128-129 ° C, 1 H-NMR (CDCl 3) δ 1.37 (3H, t, J = 6.7), 1.77 (3H, s), 1.82 (3H, s), 2.42 (3H, s), 3.22 (3H, s) 5.34 (2H, q, J = 6.7), 4.63 (2H, d, J = 6.7), 5.51 (1H, br t, J = 6.7), 7.06 (1H, d, J = 8.5), 7.20 (1H) δ d, J = 2.4, 8.5), 7.30 (1H, d, J = 1.8), 7.45-7.49 (3 H, m), 8.43-8.48 (2H, m) Ia-206 oil, δ-NMR (CDCl 3) δ 1.33 (6H, d, J = 6.1), 2.38 (3H, s), 5.16 (2H, s), 5.55 (1 H, sept, J = 6.1), 5.68 (1 H, s) 6.75 (1H, dd, J = 1.8, 8.5), 6.89 (1H, d, J = 1.8), 6.99 (1H, d, J = 8.5), 7.36-7.48 (8H, m), 8.42-8.47 (1H); 2H, m)

9999

9

9

191

Table 97

Ia-207 123-124 ° C, 1 H-NMR (CDCl 3) δ 1.33 (3H, s), 1.36 (3H, s), 2.41 (3H, s), 3.11 (3H, s), 5.18 (2H, s), 5.55 ( 1H, sept, J = 6.1., 7.13 (1H, d, J = 8.5), 7.20 (1H, dd, J = 1.8, 8.5), 7.31 (1H, d, J = 1.8), 7.37-7.50 (8H, m), 8.42-8.46 (2 H, m) Ia-208 157-158 ° C, Ή-NMR (CDCl 3) δ 1.32 (3H, s), 1.34 (3H, s), 2.38 (3H, s), 2.40 (3H, s), 5.11 (2H, s), 5.55 ( 1H, sept, J = 6.1, 5.68 (1H, s), 6.75 (1H, dd, J = 2.4, 8.5), 6.88 (1H, d, J = 2.4), 6.99 (1H, d, J = 8.5) 7.24 (1H, d, J = 7.9); 7.36 (2H, d, J = 7.9); 7.45-7.52 (3H, m); 8.42-8.47 (2H, m); Ia-209 159-160 ° C, 1 H-NMR (CDCl 3) δ 1.33 (3H, s), 1.35 (3H, s), 2.39 (3H, s), 2.41 (3H, s), 3.10 (3H, s), 5.13 ( 2H, s), 5.55 (1 H, sept, J = 6.1), 7.13 (1 H, d, J = 7.9), 7.18 (1 H, d, J = 1.8), 7.23 (1 H, d, J = 7.3), 7.30 (1H, d, J = 1.8), 7.36 (2H, d, J = 7.9), 7.44-7.49 (3 H, m), 8.42-8.46 (2H, m) Ia-210 113-114 ° C, 1 H-NMR (CDCl 3) δ 1.32 (3H, s), 1.34 (3H, s), 1.77 (3H, s), 1.83 (3H, s), 2H, d, J = 7.3, 5.49-5.59 (2H, m), 5.70 (1H, s), 6.73 (1H, dd, J = 2.4, 8.5), 6.86 (1H, d, J = 2.4), 6.92 (1H, d, J = 8.5); 7.45-7.50 (3H. M); 8.42-8.46 (2H. M) Ia-211 128-129 ° C, 1 H-NMR (CDCl 3) δ 1.33 (3H, s), 1.35 (3H, s), 1.77 (3H, s), 1.82 (3H, s), 2.41 (3H, s), 3.22 ( 3H, s), 4.64 (2 H, d, J = 6.7), 5.49-5.60 (2 H, m), 7.05 (1 H, d, J = 8.5), 7.18 (1 H, dd, J = 1.8, 8.5), 7.29 (1H, d, J = 2.4), 7.45-7.49 (3 H, m), 8.42-8.46 (2 H, m) Ia-214 110-111 ° C, δ-NMR (CDCl 3) δ 1.24 (3H, t, J = 7.6), 2.65 (2H, q, J = 7.6), 4.02 (3H, s), 5.16 (2H, s), 5.71 (1H, d), 6.74 (1H, dd, J = 2.0, 8.3), 6.88 (1H, d, J = 2.0), 7.01 (1H, d, J = 8.3), 7.41-7.49 (8H, m), 8.48-8.53 (2 H, m) Ia-215 161-162 ° C, δ-NMR (CDCl 3) δ 1.25 (3H, t, J = 7.6), 2.66 (2H, q, J = 7.6), 3.11 (3 H, s), 4.02 (3 H, s), 5.17 (2H, s), 7.14 (1 H, d, J = 8.5), 7.18 (1 H, dd, J = 2.0, 8.5), 7.28 (1 H, d, J = 2.0), 7.37-7.49 (8H, m), 8.49-8.53 (2 H, m) Ia-216 121-122 ° C, δ-NMR (CDCl 3) δ 1.24 (3H, t, J = 7.6), 2.40 (3H, s), 2.65 (2H, q, J = 7.6), 4.02 (3H, s), 5.11 (2H, s), 5.70 (1 H, s), 6.74 (1 H, dd, J = 2.0, 8.3), 6.87 (1 H, d, J = 2.0), 7.01 (1 H, d, J = 8.3), 7.24 ( 2H, d, J = 8.1. 7.34 (2H, d, J = 8.1); 7.46-7.50 (3H, m); 8.49-8.53 (2H, m); Ia-217 184-185 ° C, δ-NMR (CDCl 3) δ 1.25 (3H, t, J = 7.6), 2.39 (3 H, s), 2.66 (2H, q, J = 7.6), 3.10 (3 H, s), 4.02 (3H, s), 5.13 (2H, d), 7.14 (1H, d, J = 8.6), 7.18 (1H, dd, J = 2.0, 8.6), 7.22 (2H, d, J = 7.8), 7.27 ( 1 H, d, J = 2.0), 7.36 (2H, d, J = 7.8), 7.47-7.51 (3 H, m), 8.49-8.53 (2H, m) Ia-218 119-120 ° C, δ-NMR (CDCl 3) δ 1.24 (3H, t, J = 7.6), 1.77 (3H, s), 1.83 (3H, s), 2.65 (2H, q, J = 7.6), 4.02 (3H, s), 4.62 (2 H, d, J = 6.8), 5.51 (1 H, br t, J = 6.8), 5.73 (1 H, s), 6.73 (1 H, dd, J = 2.0, 8.3), 6.85 (1H, d, J = 2.0), 6.94 (1H, d, J = 8.3), 7.46-7.50 (3 H, m), 8.49-8.53 (2H, m) Ia-219 141-142 ° C, δ-NMR (CDCl 3) δ 1.25 (3H, t, J = 7.6), 1.77 (3H, s), 1.82 (3H, s), 2.66 (2H, q, J = 7.6), 3.22 (3H, s), 4.02 (3H, s), 4.63 (2 H, d, J = 6.6), 5.51 (1 H, br t, J = 6.6), 7.07 (1 H, d, J = 8.5), 7.17 (1 H) δ d, J = 2.0, 8.5), 7.26 (1H, d, J = 2.0), 7.46-7.50 (3 H, m), 8.49-8.53 (2H, m) Ia-222 187-189 ° C, δ-NMR (CDCl 3) δ 5.18 (2H, s), 5.76 (1H, s), 6.93 (1H, dd, J = 2.2, 8.3), 7.04 (1H, d, J = 8.6) 7.05 (1H, d, J = 2.2); 7.42-7.58 (8H, m); 8.45-8.49 (2H. M); 8.97 (1H, s). Ia-223 163-166 ° C, 1 H-NMR (CDCl 3) δ 3.13 (3H, s), 5.21 (2H, s), 7.19 (1 H, d, J = 8.5), 7.36 (1 H, dd, J = 2.0, 8.5) 7.38-7.54 (9H, m), 8.45-8.49 (2 H, m), 8.99 (2 H, s)

192 ·

Table 98

Ia-224 165-166 ° C, 1 H-NMR (CDCl 3) δ 1.78 (3H, s), 1.83 (3H, s), 4.65 (2H, d, J = 6.8), 5.53 (1H, t, J = 6.8), 5.77 (1H, d), 6.92 (1H, dd, J = 2.0, 8.3), 6.97 (1H, d, J = 8.3), 7.02 (1H, d, J = 2.0), 7.54-7.58 (3H, m), 8.45-8.48 (2 H, m), 8.97 (1 H, s) Ia-226 118-119 ° C, δ-NMR (CDCl 3) δ 3.87 (3H, s), 5.17 (2H, s), 5.79 (1H, s), 6.88 (1H, dd, J = 2.2, 8.3), 7.01 (1H) δ d, J = 8.3), 7.03 (1H, d, J = 2.2), 7.39-7.52 (8 H, m), 8.48-8.51 (2H, m), 8.90 (1H, s) Ia-227 117-118 ° C, Ή-NMR (CDCl 3) δ 3.13 (3H, s), 3.90 (3H, s), 5.19 (2H, s), 5.79 (1H, s), 7.18 (1H, d, J = 8.6) 7.33 (1H, dd, J = 2.2, 8.3); 7.40 (1H, d, J = 2.2); 7.41-7.53 (8H, m); 8.48-8.52 (2H. M); 8.90 (1H, s) Ia-229 92-94 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.83 (3H, s), 3.87 (3H, s), 4.63 (2H, d, J = 6.8), 5.51 (1H, t) J = 6.8, 5.78 (1H, s), 6.88 (1H, dd, J = 2.0, 8.3), 6.95 (1H, d, J = 8.3), 7.00 (1H, d, J = 2.0), 7.49- 7.51 (3H, m); 8,478.51 (2H, m); 8.90 (1 H, s) Ia-230 134-135 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.82 (3H, s), 3.23 (3H, s), 3.91 (3H, s), 4.65 (2H, d, J = 6.6) ), 5.49 (1H, t, J = 6.6), 7.11 (1H, d, J = 8.3), 7.32 (1H, dd, J = 2.0, 8.3), 7.37 (1H, d, J = 2.0), 7.49- 7.54 (3H, m), 8.48-8.52 (2 H, m), 8.90 (1 H, s) Ia-232 151-152 ° C, δ-NMR (CDCl 3) δ 2.14 (3H, s), 3.13 (3H, s), 5.21 (2H, s), 7.19 (1 H, d, J = 8.5), 7.28 (1 H, dd) J = 2.2, 8.5), 7.38-7.52 (9H, m), 8.46-8.49 (2 H, m), 8.70 (2 H, s) Ia-233 197-198 ° C, Ή-NMR (CDCl 3) δ 2.32 (3H, s), 2.60 (3H, s), 3.11 (3H, s), 5.19 (2H, s), 7.18 (2H, s), 7.28 (1H, m), 7.38-7.50 (8H, s), 8.49-8.53 (2 H, m) Ia-235 184-185 ° C, δ-NMR (CDCl 3) δ 2.23 (3H, s), 3.04 (3H, d, J = 4.6), 4.55 (1 H, br q, J = 4.6), 5.17 (2H, s), 5.82 (1 H, s), 6.71 (1 H, dd, J = 2.0, 8.1), 6.85 (1 H, d, J = 2.0), 7.04 (1 H, d, J = 8.1), 7.39-7.48 (8H, m) 8.44-8.48 (2 H, m) Ia-236 204-205 ° C, δ-NMR (CDCl 3) δ 2.23 (3H, s), 3.05 (3H, d, J = 4.6), 3.13 (3H, s), 4.51 (1 H, br q, J = 4.6), 5.19 (2H, s), 7.16 (1 H, dd, J = 2.0, 8.6), 7.19 (1 H, d, J = 8.6), 7.25 (1 H, d, J = 2.0), 7.38-7.50 (8H, m) 8.44-8.48 (2 H, m) Ia-238 oil, Ή-NMR (CDCl 3) δ 1.77 (3H, s), 1.82 (3H, s), 2.35 (3H, s), 3.99 (3H, s), 4.66 (2H, d, J = 6.7), 4.78 ( 1H, s), 5.51 (1H, br t, J = 6.7), 5.69 (1H, s), 6.91 (2H, d, J = 8.6), 6.95 (1H, d, J = 8.6), 8.01 (1H, dd, J = 8.6, 1.8), 8.07 (1 H, d, J = 1.8) Ia-239 189-190 ° C Ή-NMR (CDCl 3) δ 2.34 (3H, s), 3.21 (3H, s), 3.99 (3H, s), 5.20 (2H, s), 5.70 (1 H, s), 7.02 (1 H) δ, J = 8.6), 7.31-7.47 (9H, m), 8.03 (1 H, dd, J = 8.6, 1.8), 8.10 (1 H, d, J = 1.8) Ia-240 190-192 ° C, Ή-NMR (CDCl 3) δ 2.34 (3H, s), 3.12 (3H, s), 3.21 (3H, s), 4.00 (3H, s), 5.21 (2H, s), 7.14 ( 1 H, d, J = 8.6), 7.28-7.49 (9H, m), 8.41 (1 H, dd, J = 8.6, 2.5), 8.44 (1 H, d, J = 2.5) Ia-241 72-74 ° C, 1 H-NMR (CDCl 3) δ 1.78 (3H, s), 1.81 (3H, s), 2.34 (3H, s), 3.21 (3H, s), 3.24 (3H, s), 4.01 ( 3H, s), 4.67 (2H, d, J = 6.7), 5.50 (1 H, br t, J = 6.7), 7.08 (1 H, d, J = 8.6), 7.28-7.39 (4H, m), 8.39 ( 1H, dd, J = 8.5, 1.8), 8.42 (1 H, s) Ia-248 228-230 ° C, δ-NMR (CDCl 3) δ 5.21 (2H, s), 7.08 (1H, d, J = 9.0), 7.387.56 (8H, m), 7.72-7.76 (2H, m), 7.85 and 7.88 (each 1H, Abq, J = 9.0), 8.13-8.16 (2 H, m) Ia-249 220-221 ° C, δ-NMR (CDCl 3) δ 3.15 (3H, s), 5.23 (2H, s), 7.24 (1H, d, J = 8.8), 7.37-7.58 (8H, m), 7.89 and 7.93 (each 1H, Abq, J = 9.0), 8.07 (1 H, d, J = 2.2), 8.14-8.17 (2 H, m), 8.21 (1 H, dd, J = 2.2, 8.8)

·· ·

··· · · · · · · · · · · · · ·

Table 99

Ia-252 185-186 ° C, δ-NMR (CDCl 3) δ 1.78 (3H, s), 1.82 (3H, s), 4.66 (2H, cl, J = 6.8), 5.52 (1 H, br t, J = 6.8), 5.66 (1 H, br s), 5.78 (1 H, s), 6.99-7.03 (3 H, m), 7.68 (2 H, d, J = 9.0), 7.72 (1 H, dd, J = 2.2, 8.6), 7.82 ( 2H, s), 8.06 (2H, d, J = 8.8). Ia-253 198-200 ° C, δ-NMR (CDCl 3) δ 3.15 (3H, s), 3.21 (3H, s), 5.23 (2H, s), 7.24 (1H, d, J = 8.8), 7.38-7.46 (5H) m / z, 7.47 (2H, d, J = 9.0), 7.91 (2H, s), 8.07 (1H, d, J = 2.2), 8.19 (1H, dd, J = 2.2, 8.8), 8.22 (2H, d, J = 9.0) Ia-254 192-193 ° C, 1 H-NMR (CDCl 3) δ 1.78 (3H, s), 1.82 (3H, s), 3.21 (3H, s), 3.25 (3H, s), 4.69 (2H, d, J = 6.8) 5.51 (1H, br t, J = 6.8), 7.18 (1H, d, J = 8.8), 7.48 (2H, d, J = 9.0), 7.90 (2H, s), 8.03 (1H, d, J); = 2.2), 8.22 (1 H, dd, J = 2.2, 8.8), 8.23 (2 H, d, J = 8.8) Ia-255 233-235 ° C, δ-NMR (CDCl 3) δ 3.89 (3H, s), 5.21 (2H, s), 5.75 (1H, s), 7.05 (2H, d, J = 8.8), 7.08 (1H, d) J = 9.0), 7.37-7.47 (5H, m), 7.73-7.75 (2H, m), 7.81 and 7.83 (1H each, ABq, J = 9.3), 8.12 (2H, d, J = 8.8) Ia-256 212-215 ° C, δ-NMR (CDCl 3) δ 3.15 (3H, s), 3.89 (3H, s), 5.23 (2H, s), 7.07 (2H, d, J = 9.0), 7.23 (1H, d) J = 8.8), 7.37-7.50 (5H, m), 7.84 and 7.86 (each 1H, ABq, J = 9.3), 8.05 (1H, d, J = 2.0), 8.12 (2H, d, J = 9.0); , 8.18 (1H, dd, J = 2.0, 8.8). Ia-257 171-174 ° C, @ 1 H-NMR (CDCl3) .delta. 1.77 (3H, s), 1.82 (3H, s), 3.89 (3H, s), 4.66 (2H, d, J = 6.8), 5.52 (1H, br) t, J = 6.8, 5.78 (1 H, s), 7.01 (1 H, d, J = 8.3), 7.05 (2 H, d, J = 8.8), 7.69 (1 H, d, J = 2.2), 7.73 (1 H) , dd, J = 2.2, 8.3), 7.81 and 7.82 (each 1H, ABq, J = 9.0), 8.11 (2H, d, J = 8.8), Ia-258 197-199 ° C, 1 H-NMR (CDCl 3) δ 1.78 (3H, s), 1.82 (3H, s), 3.25 (3H, s), 3.90 (3H, s), 4.68 (2H, d, J = 6.8) ), 5.51 (1H, br t, J = 6.8), 7.06 (2H, d, J = 9.0), 7.17 (1H, d, J = 8.8), 7.84 and 7.85 (each 1H, ABq, J = 9.3), 8.00 (1 H, d, J = 2.2), 8.12 (2 H, d, J = 9.0), 8.20 (1 H, dd, J = 2.2, 8.8) Ia-269 198-199 ° C, δ-NMR (CDCl 3) δ 4.83 (1H, br s), 5.14 (2H, s), 5.69 (1H, s), 6.85 (2H, d, J = 8.8), 6.92 (1H, s, d, J = 8.3), 7.09 (1H, dd, J = 2.2, 8.3), 7.13 and 7.14 (each 1H, ABq, J = 3.9), 7.23 (1H, d, J = 2.2), 7.38-7.45 (5H) m, 7.49 (2H, d, J = 8.8) Ia-271 167-168 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.81 (3H, s), 4.60 (2H, d, J = 6.8), 4.79 (1 H, s), 5.50 (1 H, br) t, J = 6.8, 5.71 (1 H, s), 6.85 (2 H, d, J = 8.8), 6.87 (1 H, d, J = 8.3), 7.09 (1 H, dd, J = 2.2, 8.3), 7.12 and 7.14 (each 1H, ABq, J = 3.7), 7.20 (1 H, d, J = 2.2), 7.50 (2 H, d, J = 8.8) Ia-272 162-164 ° C, δ-NMR (CDCl 3) δ 3.12 (3H, s), 3.17 (3H, s), 5.16 (2H, s), 7.08 (1 H, d, J = 8.6), 7.21 (1 H, d) J = 3.7), 7.25 (1H, d, J = 3.7), 7.31 (2H, d, J = 8.8), 7.39-7.44 (5H, m), 7.48 (1H, dd, J = 2.2, 8.6), 7.57 (1 H, d, J = 2.2), 7.64 (2 H, d, J = 8.8) Ia-273 128-129 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.80 (3H, s), 3.17 (3H, s), 3.23 (3H, s), 4.62 (2H, d, J = 6.8) ), 5.48 (1H, br, J = 6.8), 7.02 (1H, d, J = 8.5), 7.20 (1H, d, J = 3.9), 7.25 (1H, d, J = 3.9), 7.31 (2H) J, 7.48 (1H, dd, J = 2.2, 8.5), 7.56 (1H, d, J = 2.2), 7.64 (2H, d, J = 8.8); Ia-275 165-166 ° C, δ-NMR (CDCl 3) δ 5.14 (4H, s), 5.69 (2H, s), 6.92 (2H, d, J = 8.3), 7.09 (2H, dd, J = 2.2, 8.3) 7.14 (2H, s), 7.27-7.44 (10H, m), 7.22 (2H, d, J = 2.2); Ia-280 178-179 ° C, Ή-NMR (CDCl 3) δ 2.31 (3H, s), 3.11 (3H, s), 4.82 (1H, s), 5.16 (2H, s), 6.84 (2H, d, J = 8.8) 7.01 (1H, s), 7.10 (1H, d, J = 8.6), 7.34-7.48 (9 H, m)

00

0 0

0000 0 0 0

1¾

0 0 0

0

0

0 0

0 0

0 0 ·

Table 100

Ia-281 128-129 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.82 (3H, s), 2.31 (3H, s), 4.61 (2H, d, J = 6.8), 4.81 (1H, s) 5.51 (1H, br t, J = 6.8), 5.72 (1H, d), 6.83 (2H, d, J = 8.8), 6.90 (1H, d, J = 8.3), 6.96 (1H, dd, J) = 2.2, 8.3), 7.00 (1 H, s), 7.08 (1 H, d, J = 2.2), 7.47 (2 H, d, J = 8.8) Ia-282 133-134 ° C, Ή-NMR (CDCl 3) δ 2.33 (3H, s), 3.12 (3H, s), 3.17 (3H, s), 5.17 (2H, s), 7.11 (1H, d, J = 8.6) 7.12 (1H, s), 7.30 (2H, d, J = 8.8), 7.35-7.48 (7H, m), 7.61 (2H, d, J = 8.8); Ia-283 86-87 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.81 (3H, s), 2.33 (3H, s), 3.17 (3H, s), 3.22 (3H, s), 4.63 ( 2H, d, J = 6.8. 5.49 (1H, br t, J = 6.8), 7.05 (1H, d, J = 8.6), 7.11 (1H, s), 7.29 (2H, d, J = 8.6), 7.36 (1 H, dd, J = 2.2, 8.6), 7.44 (1 H, d, J = 2.2), 7.61 (2 H, d, J = 8.8) Ia-309 128-129 ° C, Ή-NMR (CDCl 3) δ 2.31 (3H, s), 3.64 (3H, s), 5.15 (2H, s), 5.70 (1H, s), 6.92 (1H, dd, J = 2.0) 8.38, 6.98 (1H, d, J = 8.3), 7.07 (1H, d, J = 2.0), 7.28 (1H, br, J = 7.6), 7.38-7.47 (7H, m), 7.71 (2H) , br d, J = 7.6) Ia-310 132-133 ° C, Ή-NMR (CDCl 3) δ 2.34 (3H, s), 3.11 (3H, s), 3.65 (3H, s), 5.16 (2H, s), 7.13 (1H, d, J = 8.5) 7.29-7.48 (m, 10H), 7.70 (2H, br d, J = 7.6) Ia-311 148-149 ° C, Ή-NMR (CDCl 3) δ 2.30 (3H, s), 2.39 (3H, s), 3.64 (3H, s), 5.10 (2H, s), 5.69 (1H, s), 6.92 ( 1H, dd, J = 2.0, 8.3, 6.99 (1H, d, J = 8.3), 7.06 (1H, d, J = 2.0), 7.23 (2H, d, J = 8.1), 7.30 (1H, m) 7.33 (2H, d, J = 8.1); 7.43 (2H, br t, J = 8.1); 7.68-7.72 (2H, m) Ia-312 146-147 ° C, Ή-NMR (CDCl 3) δ 2.33 (3H, s), 2.38 (3H, s), 3.11 (3H, s), 3.65 (3H, s), 5.16 (2H, s), 7.13 ( 1 H, d, J = 8.6), 7.22 (2H, d, J = 8.1), 7.29-7.47 (7H, m), 7.68-7.72 (2 H, m) Ia-313 78-79 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.82 (3H, s), 2.33 (3H, s), 3.22 (3H, s), 3.65 (3H, s), 4.62 ( 2H, d, J = 6.8., 5.50 (1H, br t, J = 6.8), 7.06 (1H, d, J = 8.6), 7.29-7.47 (5H, m), 7.68-7.72 (2H, m) Ia-314 120-121 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.82 (3H, s), 2.30 (3H, s), 3.64 (3H, s), 4.61 (2H, d, J = 6.8) 5.52 (1H, br t, J = 6.8), 5.72 (1H, s), 6.91 (2H, br s), 7.04 (1H, br s), 7.27 (1H, br t, J = 7.3), 7.43 (2H, br t, J = 8.3), 7.70-7.73 (2 H, m) Ia-315 136-137 ° C, Ή-NMR (CDCl 3) δ 2.31 (3H, s), 3.62 (3H, s), 3.84 (3H, s), 5.16 (2H, s), 5.71 (1H, s), 6.91- 7.01 (4H, m), 7.07 (1 H, d, J = 1.8), 7.37-7.48 (5 H, m), 7.61 (2 H, d, J = 8.9) Ia-316 120-121 ° C, δ-NMR (CDCl 3) δ 2.32 (3H, s), 3.11 (3H, s), 3.63 (3H, s), 3.84 (3H, s), 5.16 (2H, s), 6.96 ( 2H, d, J = 8.9. 7.13 (1H, d, J = 6.8); 7.32-7.49 (7H, m); 7.59 (2H, d, J = 8.9); Ia-317 130-131 ° C, Ή-NMR (CDCl 3) δ 2.30 (3H, s), 2.39 (3H, s), 3.62 (3H, s), 3.84 (3H, s), 5.10 (2H, s), 5.70 ( 1 H, s), 6.89-7.00 (2 H, m), 6.96 (2 H, d, J = 9.2), 7.06 (1 H, d, J = 1.8), 7.23 (2 H, d, J = 7.9), 7.34 (2 H) J, 7.9, 2H, d, J = 9.2 Ia-318 145-146 ° C, Ή-NMR (CDCl 3) δ 2.33 (3H, s), 2.38 (3H, s), 3.10 (3H, s), 3.63 (3H, s), 3.85 (3H, s), 5.11 ( 2H, s), 6.97 (2H, d, J = 8.5), 7.12 (1H, d, J = 8.5), 7.22 (2H, d, J = 7.9), 7.34 (1H, d, J = 8.5), 7.35 (2H, d, J = 7.9); 7.46 (1H, d, J = 1.8); 7.57 (2H, d, J = 8.5); Ia-319 113-114 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.82 (3H, s), 2.30 (3H, s), 3.62 (3H, s), 3.84 (3H, s), 4.60 ( 2H, d, J = 6.7., 5.52 (1H, br t, J = 6.7), 6.91 (2H, d, J = 1.2), 6.96 (2H, d, J = 9.2), 7.04 (1H, s), 7.58 (2 H, d, J = 9.2)

·· ··

I 9 9 «> · · <

195

Table 101

Ia-320 66-67 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.81 (3H, s), 2.32 (3H, s), 3.22 (3H, s), 3.63 (3H, s), 3.85 ( 3H, s), 4.62 (2 H, d, J = 6.1), 5.50 (1 H, br t, J = 6.1), 6.97 (2 H, d, J = 8.5), 7.05 (1 H, d, J = 8.5), 7.34 (1 H, dd, J = 1.8, 8.5), 7.44 (1 H, d, J = 1.8), 7.57 (2 H, d, J = 8.5) Ia-322 152-153 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.82 (3H, s), 2.24 (3H, s), 3.44 (1 H, br), 3.84 (3H, s), 4.60 ( 2H, d, J = 6.7., 5.51 (1H, br t, J = 6.7.), 6.786.94 (5H, m), 7.33 (2H, d, J = 8.5). Ia-323 oil, δ-NMR (CDCl 3) δ 0.96 (3H, t, J = 7.3), 2.27 (3H, s), 3.82 (3H, s), 4.06 (2H, q, J = 7.3), 5.13 (2H, s) 6.18 (1H, dd, J = 1.8, 7.9), 6.91-6.97 (4H, m), 7.32-7.45 (7H, m). Ia-324 108-109 ° C, δ-NMR (CDCl 3) δ 0.97 (3H, t, J = 7.3), 2.28 (3H, s), 3.12 (3H, s), 3.85 (3H, s), 4.07 (2H, q) J = 7.3), 5.17 (2H, s), 6.96 (1 H, d, J = 6.7), 7.11 (1 H, d, J = 8.5), 7.24-7.49 (9H, m) Ia-325 oil, δ-NMR (CDCl 3) δ 0.99 (3H, t, J = 7.3), 1.76 (3H, s), 1.82 (3H, s), 2.28. (3H, s), 3.84., (3H, s) 4.07 (2H, q, J = 7.3), 4.61 (2H, br, J = 6.7), 5.51 (1H, br, J = 6.7), 5.78 (1H, d, J = 1.8), 6.82 (1H) δ d, J = 1.8, 8.5), 6.89-6.98 (4H, m), 7.36 (2H, d, J = 8.5). Ia-326 85-86 ° C, δ-NMR (CDCl 3) δ 0.99 (3H, t, J = 7.3), 1.76 (3H, s), 1.81 (3H, s), 2.28 (3H, s), 3.22 (3H, s) ), 4.85 (2H, d, J = 6.7), 4.85 (2H, d, J = 7.3), 4.50 (1H, br, J = 6.7), 6.96 (2H, d, J) = 8.6), 7.04 (1 H, d, J = 8.6), 7.24-7.29 (1 H, m), 7.33-7.37 (3 H, m) Ia-328 140-141 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.83 (3H, s), 2.34 (3H, s), 3.85 (3H, s), 4.52 (2H, d, J = 3.1) ), 4.62 (2H, d, J = 6.7), 5.52 (1 H, br t, J = 6.7), 5.78 (1 H, s), 6.84-7.02 (5H, m), 7.58 (2 H, d, J = 8.6) ) Ia-334 136-137 ° C, δ-NMR (CDCl 3) δ 2.13 (3H, s), 3.80 (3H, s), 5.18 (2H, s), 5.85 (1H, s), 6.83 (1H, dd, J = 2.0) 8.36, 6.96 (1H, d, J = 2.0), 7.04 (1H, d, J = 8.3), 7.32-7.46 (8H, m), 7.69-7.73 (2 H, m) Ia-335 165-165.5 ° C, δ-NMR (CDCl 3) δ 2.15 (3H, s), 3.13 (3H, s), 3.82 (3H, s), 5.20 (2H, s), 7.19 (1H, d, J = 8.3) 7.27 (1H, dd, J = 2.2, 8.3), 7.33 (1 H, m), 7.35 (1 H, d, J = 2.2), 7.38-7.50 (7 H, m), 7.67-7.71 (2 H, m) Ia-336 143-144 ° C, 1 H-NMR (CDCl 3) δ 1.78 (3H, s), 1.83 (3H, s), 2.14 (3H, s), 3.80 (3H, s), 4.64 (2H, d, J = 6.8) 5.53 (1H, br, J = 6.8), 5.84 (1H, s), 6.82 (1H, dd, J = 2.2, 8.3), 6.93 (1H, d, J = 2.2), 6.97 (1H, d, J = 8.3), 7.32 (1 H, m), 7.43 (2 H, m), 7.69-7.73 (2 H, m) Ia-337 126.5-127.5 ° C, 1 H-NMR (CDCl 3) δ 1.78 (3H, s), 1.83 (3H, s), 2.15 (3H, s), 3.24 (3H, s), 3.82 (3H, s), 4.66 ( 2H, d, J = 6.8, 5.51 (1H, brt, J = 6.8), 7.12 (1H, d, J = 8.5), 7.26 (1H, dd, J = 2.2, 8.5), 7.32 (1H, m) 7.33 (1 H, d, J = 2.2), 7.43 (2 H, m), 7.67-7.71 (2 H, m) Ia-338 167-168 ° C Ή-NMR (CDCl 3) δ 5.17 (2H, s), 5.75 (1H, s), 6.99 (1H, d, J = 8.6), 7.22 (1H, dd, J = 2.4, 8.6), 7.32 (2H, m), 7.33-7.52 (8H, m), 8.06-8.11 (2H, m) Ia-339 149-150 ° C Ή-NMR (CDCl 3) δ 3.13 (3H, s), 5.18 (2H, s), 7.14 (1 H, d, J = 8.5), 7.37-7.50 (8 H, m), 7.60 (1H, dd, J = 1.8, 8.5), 7.68 (1 H, d, J = 1.8), 8.07-8.12 (2H, m) Ia-340 184-186 ° C, δ-NMR (CDCl 3) δ 2.38 (3H, s), 5.12 (2H, s), 5.77 (1H, s), 6.99 (1H, d, J = 8.6), 7.19-7.34 (7H) m., 7.40-7 .52 (3H, m), 8.05-8.13. (2H, m) Ia-341 175-176 ° C, Ή-NMR (CDCl 3) δ 2.38 (3H, s), 3.12 (3H, s), 5.14 (2H, s), 7.14 (1 H, d, J = 8.5), 7.22 (2 H, d) J = 7.9), 7.34 (2H, d, J = 7.9), 7.37 (1 H, s), 7.47 (2 H, d, J = 1.8), 7.49 (1 H, d, J = 2.4), 7.60 (1 H, dd, J = 2.4, 8.5), 8.06-8.12 (2 H, m)

 9

4 4 · 9 9

4 4 · • * 44

19GT ··· • ·· · · · · · · ·

Table 102

Ia-342 131-132 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.82 (3H, s), 4.63 (2H, d, J = 6.7), 5.50 (1 H, br t, J = 6.7), 5.78 (1 H, s), 6.92 (1 H, d, J = 8.5), 7.22 (1 H, dd, J = 2.4, 8.5), 7.30-7.32 (2 H, m), 7.43-7.51 (3H, m), 8.07 -8.12 (2H, m) Ia-343 126-127 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.81 (3H, s), 3.25 (3H, s), 4.64 (2H, d, J = 6.7), 5.49 (1H, br) t, J = 6.7., 7.07 (1H, d, J = 8.6), 7.37 (1H, s), 7.45-7.53 (3H, m), 7.60 (1 H, dd, J = 1.8, 8.6), 7.66 (1H) , d, J = 2.4), 8.088.12 (2H, m) Ia-348 150-151 ° C, δ-NMR (CDCl 3) δ 3.85 (3H, s), 5.16 (2H, s), 5.71 (1H, s), 6.98 (4H, d, J = 8.9), 7.31-7.46 (6H) , m), 7.82 (1 H, s), 8.04 (2 H, d, J = 8.9) Ia-349 112-113 ° C, Ή-NMR (CDCl 3) δ 3.12 (3H, s), 3.88 (3H, s), 5.16 (2H, s), 6.99 (2H, d, J = 9.2), 7.12 (1H, d) J = 8.8), 7.33-7.48 (5H, m), 7.73 (1 H, dd J = 8.3, 1.8), 7.74 (1 H, s), 7.87 (1 H, s), 8.04 (2 H, d, J = 9.2) Ia-350 137-138 ° C, 1 H-NMR (CDCl 3) δ 1.75 (3H, s), 1.81 (3H, s), 3.87 (3H, s), 4.60 (2H, d, J = 6.8), 5.49 (1H, t) J = 6.8, 5.70 (1 H, s), 6.91 (1 H, d, J = 9.2), 6.98 (2 H, d, J = 9.1), 7.32-7.35 (2 H, m), 7.82 (1 H, s) 8.04 (2H, d, J = 9.1). Ia-351 127-128 ° C, 1 H-NMR (CDCl 3) δ 1.75 (3H, s), 1.81 (3H, s), 3.23 (3H, s), 3.87 (3H, s), 4.63 (2H, d, J = 6.8) ), 5.48 (1 H, t, J = 6.8), 6.98 (2 H, d, J = 9.1), 7.05 (1 H, d, J = 9.1), 7.71-7.75 (2 H, m), 7.85 (1 H, s) 8.04 (2H, d, J = 9.1). Ia-352 99-100 ° C, Ή-NMR (CDCl 3) δ 2.58 (3H, s), 3.83 (3H, s), 5.17 (2H, s), 5.71 (1H, s), 6.93-7.01 (3H, m), 7.23 (1 H, d, J = 1.9), 7.32 (1 H, d, J = 1.9), 7.34-7.44 (5 H, m), 8.01 (2 H, d, J = 9.1) Ia-353 159-160 ° C, δ-NMR (CDCl 3) δ 2.57 (3H, s), 3.11 (3H, s), 3.86 (3H, s), 5.17 (2H, s), 6.97 (2H, d, J = 9.1) 7.13 (1H, d, J = 8.5); 7.35-7.47 (5H, m); 7.65 (2H, d, J = 9.1); 7.99 (2H, d, J = 9.1); Ia-354 oil, δ-NMR (CDCl 3) δ 1.76 (3H, s), 1.81 (3H, s), 2.16 (3H, s), 2.57 (3H, s), 3.86 (3H, s), 4.61 (2H, d, J = 6.7), 5.50 (1 H, br t, J = 6.7), 5.71 (1 H, s), 6.94 (2 H, d, J = 7.3), 6.97 (1 H, d, J = 8.6), 7.23 (1 H, dd, J = 8.6, 1.8), 7.28 (1 H, d, J = 1.8), 8.00 (2 H, d, J = 7.3) Ia-355 130-131 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.81 (3H, s), 2.57 (3H, s), 3.21 (3H, s), 3.87 (3H, s), 4.63 ( 2H, d, J = 6.7., 5.49 (1H, t, J = 6.7), 6.97 (2H, d, J = 6.7), 7.07 (1H, d, J = 9.1), 7.62-7.67 (2H, m), 7.99 (2 H, d, J = 9.1) Ia-356 m.p. 91.5-92.5 ° C .; Δ NMR (CDCl 3) δ 1.74 (s, 3H), 1.76 (s, 3H), 1.77 (s, 3H), 1.80 (s, 3H), 2.34 (s, 3H), 2.54 (s, 3H), 3.74 ( d, J = 6.6Hz, 2H), 4.63 (d, J = 6.6Hz, 2H), 5.37 (brt, J = 6.6Hz, 1H), 5.54 (brt, J = 6.6Hz, 1H), 6.68 ( d, J = 8.5Hz, 2H), 7.04 (t, J = 8.5Hz, 1H), 7.19 (d, J = 8.5Hz, 2H), 7.27 (br d, J = 8.5Hz, 1H), 7.33 (dd) J = 2.0 (12.0 Hz, 1H) 7.39 (s, 1H) Ia-357 m.p. 136-136.5 [deg.] C .; Δ NMR (CDCl 3) δ 1.73 (s, 3H), 1.76 (s, 3H), 1.77 (s, 3H), 1.82 (s, 3H), 2.37 (s, 3H), 2.52 (s, 3H), 3.74 ( d, J = 6.6Hz, 2H), 4.64 (d, J = 6.8Hz, 2H), 5.35 (brt, J = 6.6Hz, 1H), 5.55 (brt, J = 6.8Hz, 1H), 6.68 ( d, J = 8.8 Hz, 2H); 7.01-7.12 (m, 3H); 7.35 (s, 1H); 7.43 (d, J = 8.8 Hz, 2H);

aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa

Table 103

Ib-3 157-158 ° C, (CDCl 3) δ 1.78 (3H, s), 1.82 (3H, s), 3.56 (3H, s), 3.62 (2H, d, J = 6.8), 5.52 (IH, s, J = 6.8), 5.69 (IH, s), 5.84 (IH, s), 6.95 (4H, d, J = 2.4), 7.05 (IH, s), 7.76 (IH, td, J = 7.8, 1.8), 7.94 (IH, d, J = 7.8), 8.75 (IH, d, J = 4.9, 2.4) Ib-8 oil, δ-NMR (CDCl 3) δ 1.76 (3H, s), 1.79 (3H, s), 2.29 (3H, s), 2.37 (3H, s), 3.89 (3H, s), 4.64 (2H, d, J = 6.7), 5.57 (IH, brt, J = 6.7), 6.85-6.96 (3H, m), 7.16 (IH, s), 7.22-7.27 (IH, m), 7.33 (IH, s), 7.46 (IH, d, J = 7.9), 7.75 (IH, dt, J = 1.8, 7.9), 8.71 (IH, dd, J = 4.9, 1.8), Ib-11 112-113 ° C, 1 H-NMR (CDCl 3) δ 1.45 (3H, s), 1.73 (3H, s), 1.76 (3H, s), 1.81 (3H, s), 2.67 (3H, s), 3.25 ( 3H, s), 3.68 (3H, s), 4.39 (2H, d, J = 7.3), 4.39 (2H, d, J = 6.8), 5.27 (1H, t, J = 7.3) ), 5.49 (1H, t, J = 6.8), 7.09 (IH, d, J = 8.5), 7.33-7.39 (2H, ra), 7.49 (IH, s), 7.60 (IH, dd, J = 8.5, 2.5), 8.16 (IH, d, J = 8.5), 8.56 (IH, d, J = 1.8) Ib-12 139-141 ° C, Ή-NMR (CDCl 3) δ 2.66 (3H, s), 3.12 (3H, s), 3.64 (3H, s), 3.82 (3H, s), 3.84 (2H, brs), 5.18 ( 2H, s), 7.05 (1H, dd, J = 8.5, 3.0), 7.14 (IH, d, J = 8.5), 7.32-7.48 (8H, m), 7.86 (IH, d, J = 8.5), 8.21 (IH, d, J = 3.0) Ib-13 oil, δ-NMR (CDCl 3) δ 1.76 (3H, s), 1.79 (3H, s), 2.28 (3H, s), 2.36 (3H, s), 3.73 (2H, br s), 3.88 (3H, s) ), 4.63 (2H, d, J = 6.8), 5.57 (1H, br t, J = 6.8), 6.84-6.95 (3H, m), 7.06 (1H, dd, J = 2.9, 8.3), 7.14 (1H); IH, s), 7.25 (IH, dd, J = 0.5, 8.3), 8.20 (IH, dd, J = 0.5, 2.9) Ib-15 157-158 ° C, Ή-NMR (CDCl3) δ 2.30 (3H, s), 2.35 (3H, s), 2.99 (6H, s), 3.70 (2H, brs), 6.79 (2H, d, J = 8.9) 7.05 (IH, dd, J = 8.5, 2.4), 7.13 (IH, s), 7.247.29 (4H, m), 8.20 (IH, d, J = 2.4) Ib-16 164-165 ° C, 1 H-NMR (CDCl 3) δ 1.75 (3H, s), 1.78 (3H, s), 1.81 (3H, s), 3.56 (3H, s), 3.77 (2H, d, J = 6.8) ), 3.79 (3H, s), 4.61 (2H, d, J = 7.3), 5.34 (1H, t, J = 6.8), 5.53 (IH, t, J = 7.3), 5.68 (IH, s), 5.85 (IH, d), 6.92-6.98 (4H, m), 7.05 (IH, d), 7.77 (IH, d, J = 9.2), 8.14 (IH, d, J = 3.1) Ib-17 oil, δ-NMR (CDCl 3) δ 1.75 (6H, s), 1.78 (3H, s), 1.79 (3H, s), 2.29 (3H, s), 2.37 (3H, s), 3.76 (2H, d, J = 6.6, 3.88 (3H, s), 4.63 (2H, d, J = 6.8), 5.35 (IH, brt, J = 6.6), 5.57 (IH, brt, J = 6.8), 6.84-6.98 (4H, m), 7.13 (IH, s, J) = 7.27 (IH, d, J = 8.6), 7.31 (IH, s), 8.13 (IH, d, J = 2.4) Ib-20 116-117 ° C, Ή-NMR (CDCl3) δ 1.75 (3H, s), 1.78 (3H, s), 2.30 (3H, s), 2.36 (3H, s), 2.99 (6H, s), 3.75 ( 2H, d, J = 6.8, 5.35 (2H, t, J = 6.8), 6.90 (2H, d, J = 8.5), 6.94 (IH, dd, J = 8.5, 3.1), 7.13 (IH, s) 7.22-7.29 (4H, m), 8.13 (IH, d, J = 2.4); Ib-21 233-234 ° C, Ή-NMR (CDCl 3) δ 2.65 (3H, s), 3.13 (3H, s), 3.69 (3H, s), 3.84 (3H, s), 5.19 (2H, s), 7.15 ( 1H, d, J = 8.5, 7.33-7.48 (8H, m), 8.10 (IH, brs), 8.16 (2H, d, J = 1.4), 8.88 (IH, s) Ib-23 152-153 ° C, 1 H-NMR (CDCl 3) δ 1.75 (3H, s), 1.79 (3H, s), 2.30 (3H, s), 2.37 (3H, s), 3.88 (3H, s), 4.63 ( 2H, d, J = 6.6, 5.56 (IH, brt, J = 6.6), 6.84-6.96 (3H, m), 7.17 (IH, s), 7.32 (IH, s), 7.53 (IH, d, J = 8.5), 8.25 (IH, dd, J = 2.7, 8.5), 8.76 (IH, d, J = 2.7) Ib-25 178-180 ° C, δ-NMR (CDCl 3) δ 2.32 (3H, s), 2.37 (3H, s), 3.00 (6H, s), 6.80 (2H, d, J = 9.1), 7.17 (1H, s) ), 7.25 (2H, d, J = 8.5), 7.32 (IH, s), 7.53 (IH, d, J = 8.5), 8.05 (IH, brs), 8.24 (IH, dd, J = 8.5, 2.5) 8.74 (IH, d, J = 2.5). Ib-35 219-221 ° C, δ-NMR (CDCl 3) δ 3.00 (6H, s), 3.09 (3H, s), 3.84 (3H, s), 3.86 (3H, s), 6.50 (IH, br), 6.80 ( 2H, d, J = 9.0, 6.99 (IH, s), 7.51 (2H, d, J = 9.0), 7.52 (IH, s), 7.71 (IH, dd, J = 2.7, 8.7), 8.02 (IH) (d, J = 8.7), 8.52 (IH, d, J = 2.7)

9

196 *

4

I ·

I · ···

944 ·

Table 104

Ib-37 187-190 ° C, Ή-NMR (CDCl 3) δ 2.32 (3H, s), 2.36 (3H, s), 3.00 (6H, s), 3.10 (3H, s), 6.66 (1 H, brs), 6.80 ( 2H, d, J = 9.2), 7.16 (1H, s), 7.18-7.32 (3H, m), 7.48 (1 H, d, J = 8.5), 7.76 (1 H, dd, J = 8.5, 3.1), 8.51 (1 H, d, J = 3.1) Ib-39 169-170 ° C, δ-NMR (CDCl 3) δ 2.67 (3H, s), 3.06 (6H, s), 3.13 (3H, s), 3.65 (3H, s), 3.83 (3H, s), 5.18 ( 2H, s), 7.04 (1 H, dd, J = 8.5, 3.0), 7.13 (1 H, d, J = 8.5), 7.32-7.47 (8H, m), 7.93 (1 H, d, J = 8.5), 8.25 (1 H, d, J = 3.0) Ib-40 205-206 ° C, 1 H-NMR (CDCl 3) δ 1.73 (3H, s), 1.81 (3H, s), 3.06 (6H, s), 3.59 (3H, s), 3.80 (3H, s), 4.61 ( 2H, d, J = 6.8. 5.51 (1H, t, J = 6.8), 5.70 (1H, brs), 5.87 (1H, brs), 6.92 (3H, s), 7.04-7.10 (2H, m), 7.82 (1 H, d, J = 8.5), 8.24 (1 H, d, J = 1.8) Ib-41 157-158 ° C, 1 H-NMR (CDCl 3) δ 1.74 (3H, s), 1.81 (3H, s), 2.70 (3H, s), 3.05 (6H, s), 3.21 (3H, s), 3.61 ( 3H, s), 3.81 (3H, s), 4.61 (2 H, d, J = 6.8), 5.51 (1 H, t, J = 6.8), 7.03-7.11 (2 H, m), 7.33 (1 H, dd, J) - 8.5, 2.0), 7.38 (1H, d, J = 2.0), 7.41 (1H, d), 7.92 (1H, d, J = 8.5), 8.24 (1H, d, J = 2.0) Ib-44 117-118 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.80 (3H, s), 2.29 (3H, s), 2.36 (3H, s), 3.04 (6H, s), 3.89 ( 3H, s), 4.63 (2H, d, J = 6.8), 5.57 (1 H, br t, J = 6.8), 6.86-6.95 (3 H, m), 7.08 (1 H, dd, J = 2.9, 8.6), 7.14 (1 H, s), 7.31 (1 H, s), 7.32 (1 H, d, J = 8.6), 8.22 (1 H, d, J = 2.9) Ib-46 216-218 ° C, Ή-NMR (CDCl 3) δ 3.64 (3H, s), 3.82 (3H, s), 5.16 (2H, s), 5.73 (1H, s), 5.77 (1H, s), 6.94 ( 1 H, dd, J = 8.5, 2.4), 7.07 (1 H, s), 7.09 (2 H, d, J = 6.7), 7.36-7.47 (5 H, m), 8.25 (1 H, d, J = 8.5), 8.54 (1H, dd, J = 8.5, 2.4); 9.54 (1H, d, J = 2.4). Ib-47 159-160 ° C, δ-NMR (CDCl 3) δ 2.63 (3H, s), 3.14 (3H, s), 3.73 (3H, s), 3.86 (3H, s), 5.19 (2H, s), 7.16 (3H, s) 2H, d, J = 8.5), 7.29-7.48 (6H, m), 7.56 (1 H, s), 8.35 (1 H, d, J = 9.1), 8.54 (1 H, dd, J = 9.1, 2.5), 9.54 (1 H, d, J = 2.5) Ib-49 194-195 ° C, Ή-NMR (CDCl 3) δ 2.35 (3H, s), 2.41 (3H, s), 3.01 (6H, s), 6.80 (2H, d, J = 9.1), 7.20 (1H, s) 7.27 (2H, d, J = 9.1), 7.37 (1H, d), 7.67 (1H, d, J = 9.1), 8.53 (1H, dd, J = 9.1, 2.5), 9.53 (1H, d, J = 2.4) Ib-51 126-127 ° C, Ή-NMR (CDCl 3) δ 2.25 (3H, s), 2.32 (3H, s), 3.01 (6H, s), 6.80 (2H, d, J = 8.5), 7.09 (1H, s) 7.18 (1H, s), 7.22-7.29 (2H, m), 7.38 (1 H, d, J = 8.5), 7.66 (1 H, dd, J = 8.0, 2.4), 8.76 (1 H, d, J = 2.4) Ib-54 162-163 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.82 (3H, s), 3.48 (3H, s), 3.76 (3H, s), 4.62 (2H, d, J = 6.8) 5.53 (1H, t, J = 6.8), 5.72 (1H, s), 5.81 (1H, s), 6.47 (1H, s), 6.94-6.99 (2H, m), 7.04 (1H, s), 7.37-7.68 (4H, m), 7.99 (1 H, dd, J = 6.1, 1.8) 8.62 (1 H, d, J = 4.9), 8.89 (1 H, d, J = 1.8), Ib-58 oil, δ-NMR (CDCl 3) δ 1.76 (3H, s), 1.80 (3H, s), 2.28 (3H, s), 2.30 (3H, s), 3.89 (3H, s), 4.64 (2H, d, J = 6.7), 5.57 (1 H, br t, J = 6.7), 6.86-6.96 (3H, m), 7.13 (1 H, s), 7.19 (1 H, s), 7.36 (1 H, dd, J = 8.2, 4.9), 7.70 (1 H, dt, J = 1.8, 8.2), 8.60 (1 H, dd, J = 4.9, 1.8), 8.65 (1 H, d, J = 1.8) Ib-65 180-181 ° C, Ή-NMR (CDCl 3) δ 2.28 (3H, s), 2.31 (3H, s), 3.00 (6H, s), 4.45 (2H, br s), 6.57 (1 H, d, J = 9.1), 6.80 (2H, d, J = 9.1), 7.09 (1 H, s), 7.15 (1 H, s), 7.25 (2 H, dd, J = 8.0, 2.4), 7.47 (1 H, dd, J = 8.5) (2.4), 8.10 (1 H, d, J = 2.4) Ib-67 185-188 ° C 1 H-NMR (CDCl 3) δ 2.07 (3H, s), 2.21 (3H, s), 2.28 (3H, s), 3.00 (6H, s), 4.41 (2H, s), 6.41 (1H) δ d, J = 7.8), 6.80 (2H, d, J = 9.2), 6.97 (1 H, s), 7.12 (1 H, s), 7.22-7.29 (3 H, m)

• φφ • φ · · φφφ φ φφφ i9 <r ·· * ··> ····

• Φ φ · · · φ φ φ φ φ φ φ φ φ

Table 105

Ib-69 mp 184-185.5 ° C; Δ NMR (CDCl 3) δ 1.75 (s, 3H), 1.77 (s, 3H), 2.29 (s, 3H), 2.30 (s, 3H), 3.00 (s, 6H), 3.90 (s, J = 5.6 Hz) (2H), 4.45 (brs, 1H), 5.37 (brt, J = 5.6Hz, 1H), 6.45 (dd, J = 0.5Hz, 8.5Hz, 1H), 6.80 (d, J = 8.8Hz, 2H) 7.17 (d, J = 8.8 Hz, 2H), 7.10 (s, 1H), 7.17 (dd, J = 8.8 Hz, 2H), 8.17 (dd, J = 0.5, 2.4) Hz, 1H) Ib-71 118-119 ° C, 1 H-NMR (CDCl 3) δ 1.73 (3H, s), 1.76 (3H, s), 2.08 (3H, s), 2.20 (3H, s), 2.28 (3H, s), 3.00 ( 6H, s), 3.83 (2 H, d, J = 6.8), 4.81 (1 H, brs), 5.35 (1 H, t, J = 6.7), 6.29 (1 H, d, J = 8.5), 6.79 (2H, d) J = 8.5), 6.97 (1 H, s), 7.12 (1 H, s), 7.24-7.29 (3 H, m) Ib-73 196-197 ° C, δ-NMR (CDCl 3) δ 2.25 (3H, s), 2.27 (3H, s), 2.32 (3H, s), 3.02 (6H, s), 6.86 (2H, d, J = 8.5) 7.17 (1H, s), 7.28 (2H, d, J = 8.5), 7.75 (1H, dd, J = 8.0, 2.4), 8.19 (1H, br s), 8.25- 8.27 (2H, m) Ib-75 169-171 ° C, δ-NMR (CDCl 3) δ 2.05 (3H, s), 2.22 (3H, s), 2.27 (3H, s), 2.29 (3H, s), 3.01 (6H, s), 6.80 ( 2H, d, J = 8.5, 6.97 (1H, s), 7.14 (1H, s), 7.28 (1H, d, J = 8.5), 7.49 (1H, d, J = 8.5), 7.92 (1H, brs) 8.05 (1H, d, J = 8.5) Ib-79 149-152 ° C, δ-NMR (CDCl 3) δ 2.07 (3H, s), 2.28 (3H, s), 2.29 (3H, s), 3.00 (6H, s), 3.19 (3H, s), 6.80 ( 2H, d, J = 9.1., 6.94 (1H, s), 7.03 (1H, d, J = 8.5), 7.15 (1H, s), 7.24-7.27 (2H, m), 7.47 (1H, d, J) = 8.5) Ib-81 164-165 ° C, δ-NMR (CDCl 3) δ 2.69 (3H, s), 3.12 (3H, s), 3.16 (6H, s), 3.59 (3H, s), 3.77 (3H, s), 5.18 ( 2H, s), 6.59 (1 H, d, J = 8.5), 6.84 (1 H, s), 7.14 (1 H, d, J = 8.5), 7.32-7.48 (7 H, m), 7.84 (1 H, dd, J) = 8.5, 2.4), 8.40 (1 H, d, J = 2.4) Ib-82 72-74 ° C, 1 H-NMR (CDCl 3) δ 1.75 (3H, s), 1.82 (3H, s), 3.16 (6H, s), 3.52 (3H, s), 3.74 (3H, s), 4.62 ( 2H, d, J = 6.8, 5.52 (1H, t, J = 6.8), 5.68 (1H, s), 5.85 (1H, s), 6.45 (1H, s), 6.61 (1H, d, J = 9.1) ), 6.94 (2H, d, J = 1.8), 7.05 (1H, d, J = 1.2), 7.81 (1H, dd, J = 8.5, 2.4) 8.46 (1H, d, J = 2.4), Ib-83 132-133 ° C, 1 H-NMR (CDCl 3) δ 1.75 (3H, s), 1.81 (3H, s), 2.71 (3H, s), 3.15 (6H, s), 3.25 (3H, s), 3.61 ( 3H, s), 3.77 (3H, s), 4.62 (2 H, d, J = 6.8), 5.52 (1 H, t, J = 6.8), 6.59 (1 H, d, J = 8.5), 6.83 (1 H, s) ), 7.07 (1H, d, J = 8.5), 7.34 (1H, dd, J = 8.5, 1.8), 7.38 (1H, d, J = 1.8), 7.83 (1H, dd, J = 6.1, 1.2), 8.39 (1 H, d, J = 1.2) Ib-90 91-91.5 ° C, 1 H-NMR (CDCl 3) δ 1.79 (3H, s), 1.82 (3H, s), 2.27 (3H, s), 2.31 (3H, s), 3.00 (6H, s), 4.87 ( 2H, d, J = 7.1), 5.57 (1 H, br t, J = 7.1), 6.79-6.83 (3 H, m), 7.10 (1 H, s), 7.16 (1 H, s), 7.27 (2H, d, J = 8.8), 7.59 (1 H, dd, J = 2.4, 8.3), 8.17 (1 H, dd, J = 0.7, 2.4) Ib-99 239-241 ° C, δ-NMR (CDCl 3) δ 2.28 (3H, s), 2.34 (3H, s), 3.02 (6H, s), 3.30 (3H, s), 6.81 (2H, d, J = 8.8) 7.26 (2H, d, J = 8.8), 7.95 (1 H, dd, J = 2.2, 8.0), 8.15 (1 H, dd, J = 0.7, 8.0), 8.75 (1 H, dd, J = 0.7, 2.2) Ib-101 159-160 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.82 (3H, s), 3.50 (3H, s), 3.76 (3H, s), 4.62 (2H, d, J = 6.8) 5.53 (1 H, t, J = 6.8), 5.73 (1 H, s), 5.84 (1 H, s), 6.48 (1 H, s), 6.91-6.99 (2 H, m), 7.04 (1 H, d, J) = 1.8), 7.59 (2H, d, J = 5.5), 8.70 (2H, d, J = 5.5), Ib-105 113-114 ° C, 2.28 (3H, s), 2.29 (3H, s), 3.91 (3H, s), 5.21 (2H, s), 6.83 (1 H, dd, J = 2.0, 8.3), 6.90 (1 H) δ d, J = 2.0), 6.95 (lH, d, J = 8.3), 7.12 (lH, s), 7.17 (lH, s), 7.30 (lH, d, J = 6.1), 7.31-7.50 (5H, m), 8.65 (2 H, d, J = 6.1) Ib-124 157-158 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.82 (3H, s), 3.66 (3H, s), 3.80 (3H, s), 4.05 (3H, s), 4.62 ( 2H, d, J = 6.8, 5.52 (1H, t, J = 6.8), 5.72 (1H, s), 5.78 (1H, s), 6.89-6.98 (2H, m), 7.03 (1H, d, J) = 1.8) 7.09 (1 H, s), 7.45 (1 H, d, J = 1.2) 8.89 (1 H, d, J = 1.2)

20Q • 00 0 0 0

0 0 · 00 0 0

0 00

00-00

0 00

00 0 0 0 0 0

0 0 0 0

0 0 0 0 0 0 0 0 0 0 * 0 · 00

Table 106

Ib-127 99-100 ° C, Ή-NMR (CDCl 3) δ 2.32 (3H, s), 2.40 (3H, s), 3.03 (6H, s), 4.04 (3H, s), 6.79 (2H, d, J = 8.7) 6.87 (1H, s), 7.16 (1H, s), 7.25 (2H, d, J = 7.3), 7.34 (1H, s), 8.86 (1H, d, J = 1.2) Ib-145 184-185 ° C, δ-NMR (CDCl 3) δ 2.60 (3H, s), 3.14 (3H, s), 3.71 (3H, s), 3.84 (3H, s), 5.19 (2H, s), 7.16 ( 1 H, d, J = 7.9), 7.33 (7H, m), 7.58 (1 H, d, J = 8.6), 7.59 (1 H, s), 8.24 (1 H, d, J = 9.2) Ib-146 154-155 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.82 (3H, s), 3.62 (3H, s), 3.80 (3H, s), 4.62 (2H, d, J = 6.8) 5.53 (1H, t, J = 6.8), 5.69 (1H, s), 5.76 (1H, s), 6.89-7.03 (3H, m), 7.12 (1H, s), 7.57 (1H, d, J) = 8.5) 8.14 (1 H, d, J = 9.2) Ib-147 195-196 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.81 (3H, s), 2.64 (3H, s), 3.26 (3H, s), 3.71 (3H, s), 3.84 ( 3H, s), 4.64 (2 H, d, J = 6.8), 5.49 (1 H, t, J = 6.8), 7.10 (1 H, d, J = 8.6), 7.34 (1 H, dd, J = 8.5, 1.8) 7.39 (1H, d, J = 1.8) 7.59 (1H, s), 7.58 (1H, d, J = 9.2), 8.23 (1H, d, J = 9.2) Ib-150 197-198 ° C, Ή-NMR (CDCl 3) δ 2.34 (3H, s), 2.39 (3H, s), 3.01 (6H, s), 6.81 (2H, d, J = 9.1), 7.21 (1H, s) 7.26 (2H, d, J = 8.5), 7.34 (1H, s), 7.58 (2H, d, J = 4.2) Ib-154 185-186 ° C, Ή-NMR (CDCl 3) δ 2.61 (3H, s), 3.14 (3H, s), 3.25 (6H, s), 3.67 (3H, s), 3.81 (3H, s), 5.19 ( 2H, s), 6.85 (1 H, d, J = 9.7), 7.14 (1 H, d, J = 8.8), 7.33-7.48 (7 H, m), 7.65 (1 H, s), 8.02 (1 H, d, J = 9.7) Ib-162 188-189 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.82 (3H, s), 3.60 (3H, s), 3.79 (3H, s), 4.21 (3H, s), 4.62 ( 2H, d, J = 6.8, 5.52 (1H, t, J = 6.8), 5.69 (1H, s), 5.72 (1H, s), 6.91-7.07 (4H, m), 7.13 (1H, s), 8.06 (1 H, d, J = 9.8) Ib-165 152-153 ° C, Ή-NMR (CDCl 3) δ 2.33 (3H, s), 2.39 (3H, s), 3.01 (6H, s), 4.19 (3H, s), 6.80 (2H, d, J = 9.1) ), 7.03 (1H, d, J = 9.1), 7.19 (1H, s), 7.26 (2H, d, J = 7.8), 7.33 (1H, s), 7.53 (1H, d, J = 9.1) Ib-168 oil, δ-NMR (CDCl 3) δ 1.77 (3H, s), 1.82 (3H, s), 3.65 (3H, s), 3.81 (3H, s), 4.63 (2H, d, J = 6.7), 5.53 ( 1H, br t, J = 6.7., 5.74 (1H, s), 5.77 (1H, s), 6.926.99 (3H, m), 7.04 (1H, d, J = 1.8), 8.53 (1H, d, J = 1.8), 8.69 (1 H, s), 9.25 (1 H, s) Ib-169 165-166 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.81 (3H, s), 2.72 (3H, s), 3.24 (3H, s), 3.77 (3H, s), 3.84 ( 3H, s), 4.64 (2 H, d, J = 6.8), 5.49 (1 H, t, J = 6.8), 7.10 (1 H, d, J = 8.5), 7.35 (1 H, dd, J = 8.5, 2.4) 7.41 (1H, s, J = 2.4), 7.45 (1H, s), 8.57 (1H, s), 8.69 (1H, s), 9.32 (1H, s) Ib-188 165-168 ° C, Ή-NMR (CDCl 3) δ 2.29 (3H, s), 2.42 (3H, s), 3.00 (6H, s), 4.46 (2H, br s), 5.31 (1H, s), 6.78 (2H, d, J = 8.5), 7.11 (1 H, s), 7.23 (2 H, d, J = 8.5), 7.38 (1 H, s), Ib-198 103-104 ° C, Ή-NMR (CDCl 3) δ 2.28 (3H, s), 2.43 (3H, s), 2.99 (6H, s), 3.50 (2H, s), 3.74 (3H, s), 5.76 (1H, s), 6.79 (2H, d, J = 8.5), 7.09 (1H, s), 7.24 (2H, d, J = 8.5), 7.43 (1H, s) Ib-200 oil, δ-NMR (CDCl 3) δ 1.73 (3H, s), 1.76 (3H, s), 2.29 (3H, s), 2.46 (3H, s), 2.99 (6H, s), 3.16 (1H, brs) 3.68 (2H, d, J = 5.5), 3.68 (3H, s), 5.37 (1 H, br t, J = 5.5), 6.79 (2 H, d, J = 9.2), 7.10 (1H, s), 7.24 (2H, d, J = 9.2), 7.44 (1 H, s) Ib-202 174-177 ° C Ή-NMR (CDCl 3) δ 2.31 (3H, s), 2.43 (3H, s), 3.01 (6H, s), 3.12 (3H, s), 3.93 (3H, s), 6.25 (1H) , br s), 6.37 (1 H, s), 6.79 (2 H, d, J = 8.5), 7.10 (1 H, s), 7.25 (2 H, d, J = 8.5), 7.42 (1 H, s), Ib-203 234-235 ° C, δ-NMR (CDCl 3) δ 3.89 (3H, s), 3.95 (3H, s), 5.17 (2H, s), 5.56 (1 H, brs), 5.74 (1 H, brs), 6.92 ( 1 H, dd, J = 8.2, 2.0), 7.05-7.07 (2 H, m), 7.397.53 (7 H, m), 7.58 (1 H, s), 7.95 (1 H, d, J = 8.0), 8.11 (1 H) , d, J = 8.3)

φ · φ φ φ φ φ φ φ φ φ φ φ φ φ * »φ ·

9 4 · Φ • φφφ «· Φ

Φ ΦΦΦ

201 * ......

• * φφφφ

Table 107

Ib-204 197-198 ° C, δ-NMR (CDCl 3) δ 2.68 (3H, s), 3.14 (3H, s), 3.93 (3H, s), 4.05 (3H, s), 5.20 (2H, s), 7.16 (3H, s) 1 H, d, J = 7.3, 7.37-7.53 (9H, m), 7.96 (1 H, d, J = 7.3), 8.06 (1 H, s), 8.11 (1 H, d, J = 8.0) Ib-205 189-190 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.83 (3H, s), 3.89 (3H, s), 3.95 (3H, s), 4.63 (2H, d, J = 6.8) 5.53 (1H, t, J = 6.8), 5.55 (1H, s), 5.76 (1H, s), 6.89-7.03 (3H, m), 7.41 (1H, td, J = 7.3, 1.2), 7.52; (1H, d, J = 7.3, 1.2), 7.58 (1 H, s), 7.95 (1 H, d, J = 7.3), 8.11 (1 H, d, J = 7.3) Ib-206 166-167 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.81 (3H, s), 2.72 (3H, s), 3.25 (3H, s), 3.93 (3H, s), 4.05 ( 3H, s), 4.65 (2 H, d, J = 6.8), 5.49 (1 H, t, J = 6.8), 7.10 (1 H, d, J = 8.5), 7.36-7.53 (4H, m), 7.96 (1 H) δ d, J = 7.3), 8.05 δ (1H, s), 8.11 δ (1H, d, J = 8.5) Ib-207 m.p. 75-78 ° C; Δ NMR (CDCl 3) δ 1.75 (s, 3H), 1.76 (s, 3H), 1.77 (s, 3H), 1.81 (s, 3H), 2.27 (s, 3H), 2.36 (s, 3H), 3.75 ( d, J = 6.6 Hz, 2H), 4.63 (d, J = 6.6 Hz, 2H), 5.33-5.36 (m, 1 H), 5.52-5.57 (m, 1 H), 6.93-7.11 (m, 5 H), 7.24 -7.30 (m, 2H), 8.12 (d, J = 2.4 Hz, 1H) IR (KBr): 3405, 2970, 2924, 1596, 1570, 1521, 1493, 1466, 1386, 1363, 1299, 1282, 1235, 1196, 1126, 1079, 964 cm @ -1 Ib-208 b. mp 100-102 ° C; Δ NMR (CDCl 3) δ 1.76 (s, 3H), 1.81 (s, 3H), 2.27 (s, 3H), 2.34 (s, 3H), 3.73 (s, 3H), 4.63 (d, J = 6.6 Hz) (2H), 5.53-5.58 (m, 1 H), 7.00-7.11 (m, 5 H), 7.23-7.29 (m, 2 H), 8.20 (d, J = 2.4 Hz, 1 H) IR (KBr): 3422, 3326 , 3202, 2973, 2923, 1618, 1563, 1517, 1484, 1383, 1309, 1298, 1267, 1256, 1230, 1125, 1000 cm · Ib-209 m.p. 107-108 [deg.] C .; Δ NMR (CDCl 3) δ 1.77 (s, 3H), 1.81 (s, 3H), 2.31 (s, 3H), 2.40 (s, 3H), 4.64 (d, J = 6.6 Hz, 2H), 5.52-5.58 ( m, 1H), 7.02-7.11 (m, 3H), 7.18 (s, 1 H), 7.37 (s, 1 H), 7.66 (d, J = 8.7 Hz, 1H), 8.54 (dd, J = 2.4, 8.4 Hz) 1 H, 9.53 (d, J = 2.1 Hz, 1 H) IR (KBr): 3440, 2969, 1592, 1572, 1517, 1497, 1460, 1346, 1314, 1294, 1264, 1233, 1195, 1128, 990 cm; · ' Ib-210 oil,; Δ NMR (CDCl 3) δ 1.77 (s, 3H), 1.82 (s, 3H), 2.29 (s, 3H), 2.36 (s, 3H), 4.56 (d, J = 6.6 Hz, 2H), 5.54 (t, J = 6.6Hz, 1H), 6.97 (d, J = 8.1Hz, 2H), 7.15 (s, 1H), 7.25 (m, 1H), 7.28 (d, J = 8.1Hz, 2H), 7.32 (s, 1H), 7.45 (d, J = 7.5 Hz, 1H), 7.75 (td, J = 7.5, 1.8 Hz, 1H), 8.71 (d, J = 5.1 Hz, 1H). Ib-211 mp 91-92 ° C; Δ NMR (CDCl 3) δ 1.77 (s, 3H), 1.81 (s, 3H), 2.29 (s, 3H), 2.36 (s, 3H), 4.64 (d, J = 6.6 Hz, 2H), 5.55 (t, J = 6.6Hz, 1H), 6.98-7.15 (m, 4H), 7.25 (m, 1H), 7.32 (s, 1H), 7.45 (m, 1H), 75 (m, 1H), 8.71 (m, 1H); IR (KBr) 1584, 1566, 1520, 1498, 1469, 1460, 1433, 1422, 1385, 1302, 1278, 1267, 1234, 1129, 998 cm &^lt; -1 ^&gt;. Ib-212 m.p. 120-122 [deg.] C .; Δ NMR (CDCl 3) δ 1.13-1.25 (m, 4H), 1.62-1.90 (m, 4H), 1.77 (s, 3H), 1.81 (s, 3H), 2.03-2.16 (m, 2H), 2.27 (s) 3.36 (s, 3H), 3.31 (m, 1 H), 4.63 (d, J = 6.6 Hz, 2 H), 5.55 (t, J = 6.6 Hz, 1 H), 6.90-7.13 (m, 5 H) 7.21-7.32 (m, 2H); 8.10 (m. 1H); IR (KBr) 3392, 1591, 1516, 1482, 1298, 1274, 1262, 1231, 1136, 1124, 994, 835 cm &lt; -1 &gt;. Ib-213 Δ NMR (CDCl 3) δ 1.77 (s, 3H), 1.82 (s, 3H), 2.16 (s, 6H), 2.27 (s, 3H), 3.85 (s, 3H), 4.63 (d, J = 6.6Hz, 2H), 5.53-5.58 (m, 1 H), 6.98-7.13 (m, 4 H), 7.22-7.30 (m, 3 H), 8.31 (t, J = 3.0 Hz, 1 H),; IR (neat): 2960, 2918, 1579, 1496, 1294, 1117, 991, 753 cm &lt; -1 &gt; Ib-214 Δ NMR (CDCl 3) δ 1.69 (s, 3H), 1.74 (s, 3H), 1.77 (s, 3H), 1.81 (s, 3H), 2.17 (s, 3H), 2.26 (s, 3H), 4.56 ( d, J = 6.6 Hz, 2H), 4.63 (d, J = 6.9 Hz, 2H), 5.34-5.39 (m, 1 H), 5.53-5.58 (m, 1 H), 7.97-7.13 (m, 4 H), 7.21 -7.29 (m, 3H), 8.30 (dd, J = 1.5, 4.5 Hz, 1H); IR (neat): 2968, 2914, 1577, 1516, 1495, 1267, 1229, 1117, 995, 841, 782 cm &lt; -1 &gt;

·· ·

202

«···

94 4 4 9

4 4 4

44

Table 108

Ib-215 mp 134-136 ° C; ¹ H NMR (CDCl 3) δ 1.77 (s, 3H); 1.82 (s. 3H); 1.93 (s. 6H); 1.94 (s. 6H); 3.78 (br. S, 2H); 4.64 (d, J = 6.6 Hz, 2H); 5.57 (m, IH); 6.73-7.13 (m. 5H); 8.24 (m, IH); IR (KBr): 3465, 3333, 3216, 2920, 1633, 1512, 1493, 1461, 1296, 1262, 1242, 1209, 1115 cm &^lt; -1 ^&gt;. Ib-216 mp 124-126 ° C; Ή NMR (CDCl 3) δ 1.76 (s, 3H); 1.77 (s. 3H); 1.79 (s. 3H); 1.82 (s. 3H); 1.93 (s. 6H); 1.95 (s. 6H); 3.74 (br. 1H); 3.77 (d, J = 6.3 Hz, 2H); 4.64 (d, J = 6.9 Hz, 2H); 5.38 (m, IH); 5.57 (m, IH); 6.73-7.10 (m. 5H); 8.14 (d, J = 2.7 Hz, 1H); IR (KBr): 3272, 2913, 1596, 1509, 1466, 1302, 1261, 1240, 1209, 1115 cm &^lt; -1 ^&gt;. Ib-217 mp 103-110 ° C; Ή NMR (CDCl 3) δ 1.77 (s, 3H); 1.82 (s. 3H); 1.91 (s. 6H); 1.93 (s. 6H); 4.64 (d, J = 6.6 Hz, 2H); 5.57 (m, IH); 6.74-7.23 (m. 5H); 8.28 (d, J = 2.7 Hz, 1H); IR (KBr): 3441, 2921, 1570, 1514, 1462, 1298, 1264, 1241, 1210, 1113, 1004 cm &^lt; -1 ^&gt;. Ib-218 mp 109-110 ° C; @ 1 H NMR (CDCl3) .delta. 1.78 (s, 3H), 1.82 (s, 3H), 3.77 (s, 3H), 3.78 (s, 3H), 4.87 (d, J = 7.2 Hz, 2H), 5.57 (m) 1 H, 6.45-6.55 (m, 2H), 6.81 (d, J = 8.7, Hz, 1 H), 6.83 (s, 1H), 6.91 (s, 1 H), 7.19 (t, J = 8.1 Hz, 1 H) 7.83 (dd, J = 8.7, 2.4 Hz, 1H), 8.37 (d, J = 2.4 Hz, 1H) IR (KBr): 3425, 3348, 3223, 1634, 1604, 1524, 1484, 1463, 1443, 1396, 1359, 1279, 1209, 1053, 1032, 1003, 867, 832, 782,666 cm ¹ Ib-219 mp 99-100 ° C; @ 1 H NMR (CDCl3) .delta. 1.25 (d, J = 6.3 Hz, 6H), 1.78 (s, 3H), 1.81 (s, 3H), 3.63 (m, 1H), 3.77 (s) 3.87 (s, 3H), 4.87 (d, J = 6.9 Hz, 2H), 5.57 (m, 1H), 6.33-6.47 (m, 2H), 6.81 (d, J = 8.7 Hz, 1H) 6.92 (s, 2H), 7.20 (t, J = 8.4 Hz, 1H), 7.83 (dd, J = 8.7, 2.4 Hz, 1H), 8.36 (d, J = 2.4 Hz, 1H). IR (KBr): 3408, 1627, 1599, 1526, 1502, 1477, 1280, 1246, 1210, 1182, 1133, 1121, 1054, 1030, 968, 869, 837, 783, 668 cm ^&lt; -1 ^&gt; Ib-220 mp 139-145 ° C; Δ NMR (CDCl 3) δ 1.25 (d, J = 6.6 Hz, 6 H), 1.79 (s, 3 H), 1.82 (s, 3 H), 3.79 (s, 3 H), 3.80 (s, 3 H), 4.53 (m, 1H), 4.61 (s, 2H), 4.88 (d, J = 6.9Hz, 2H), 5.57 (m, 1H), 6.82 (d, J = 9.0Hz, 1H), 6.93 (s, 1H), 6.96 (s, 1H), 7.14-7.24 (m, 2H), 7.45 (m, 1H), 7.84 (dd, J = 9.0, 2.1Hz, 1 H), 8.37 (d, J = 2.1Hz, 1 H). IR (KBr): 3377, 3273, 1656, 1605, 1564, 1520, 1484, 1465, 1394, 1339, 1282, 1207, 1055, 1033, 1008, 984, 871, 829, 779, 688, 653, 602, 541; cm ¹ Ib-221 mp 137-138 ° Ο NMR (CDCl 3) δ 1.24 (d, J = 6.9 Hz, 6H), 1.79 (s, 3 H), 1.82 (s, 3 H), 2.78 (d, J = 5.4 Hz, 3 H) 3.79 (s, 3H), 4.17 (q, J = 5.4 Hz, 2H), 4.44 (m, 1H), 4.88 (d, J = 7.2 Hz, 2H), 5.57 (m, 1H), 6.82 (d, J = 8.7 Hz, 1H), 6.93 (s, IH), 6.96 (s, IH), 7.12-7.22 (m, 2H), 7.44 (t, J = 8.1Hz, IH), 7.84 (dd, J = 8.7, 2.7Hz, 1 H), 8.38 (d, J = 2.7Hz, 1 H) IR (KBr): 3294, 1604, 1566, 1519, 1484, 1464, 1395, 1334, 1281, 1208, 1187, 1153, 1103, 1055, 1035, 1007, 981, 870, 829, 779,688 cm ¹ Ib-222 mp 79-80 ° C; Δ NMR (CDCl 3) δ 1.73 (s, 3H), 1.77 (s, 3H), 1.78 (s, 3H), 1.81 (s, 3H), 3.71 (d, J = 6.6 Hz, 2H), 3.77 (s, 3H), 3.79 (s, 3H), 4.87 (d, J = 8.4 Hz, 2H), 5.35 (m, 1 H), 5.57 (m, 1 H), 6.36-6.48 (m, 2 H), 6.81 (d, J) = 8.4, Hz, 1H), 6.92 (s, 2H), 7.21 (t, J = 8.4 Hz, 1H), 7.83 (dd, J = 8.4, 2.4 Hz, 1H), 8.37 (d, J = 2.4 Hz, 1H) IR (KBr): 3416, 1629, 1603, 1570, 1526, 1464, 1395, 1278, 1209, 1051, 1034, 1006, 869, 830, 777, 666 cm ^&lt; -1 ^&gt;

203 • fcfc fcfc fcfcfcfc fcfc fcfc • fcfcfc fcfc fc fcfcfcfc • fcfcfc fcfc fcfc fcfc fcfc fc · fcfcfcfc fcfcfcfc ··· fcf · ···· · ·

Table 109

Ib-223 mp 103-104 ° C; Ή NMR (CDCl 3) δ 1.56 (s, 3H), 1.72 (s, 3H), 1.78 (s, 3H), 1.82 (s, 3H), 2.79 (d, J = 5.1Hz, 3H), 3.78 (s, 3.79 (s, 3H), 4.22 (q, J = 5.1 Hz, 1H), 4.28 (d, J = 6.9 Hz, 2H), 4.88 (d, J = 6.6 Hz, 2H), 5.30 (m, 1H), 5.57 (m, 1 H), 6.82 (d, J = 8.1 Hz, 1 H), 6.91 (s, 2 H), 6.95 (s, 1 H), 7.17-7.26 (m, 2 H), 7.37-7.44 (m) (1H), 7.83 (dd, J = 8.1, 2.4Hz, 1H), 8.37 (d, J = 2.4Hz, 1H); IR (KBr): 3404, 3313, 1604, 1566, 1520, 1484, 1465, 1395, 1335, 1282, 1209, 1153, 1127, 1055, 1034, 867, 828, 669 cm ¹ Ib-224 mp 95-96 ° C; Δ NMR (CDCl 3) δ 1.70 (s, 3H), 1.82 (s, 3H), 2.27 (s, 3H), 3.82 (br, 2H), 4.87 (d, J = 7.2 Hz, 2H), 5.57 (m, 1H), 6.64-6.55 (m, 2H), 6.81 (d, J = 8.4Hz, 1H), 7.50 (t, J = 8.1Hz, 1H), 7.11 (s, 1H), 7.12 (s, 1H) 7.59 (dd, J = 8.4, 2.4Hz, 1 H), 8.17 (d, J = 2.4Hz, 1 H) IR (KBr): 3436, 3328, 3218, 1634, 1622, 1606, 1556, 1522, 1480, 1460 , 1444, 1396, 1362, 1304, 1285, 1245, 1168, 1129, 1008, 834 cm ¹ Ib-225 90-91 ° C; 1 H NMR (CDCl 3) δ 1.26 (d, J = 6.3 Hz, 2H), 1.79 (s, 3H), 1.82 (s, 3H), 2.22 (s, 3H), 2.26 (s, 3H), 3.64 (m, 1 H), 4.87 (d, J = 7.5 Hz, 2H), 5.57 (m, 1 H), 6.33-6.47 ( m, 2H), 6.81 (d, J = 8.4, Hz, 1 H), 7.05 (t, J = 8.1 Hz, 1 H), 7.10 (s, 1 H), 7.13 (s, 1 H), 7.59 (dd, J = 8.4, 2.4 Hz, 1H), 8.17 (d, J = 2.4 Hz, 1H) IR (KBr): 3335, 1628, 1606, 1527, 1481, 1283, 1240, 1183, 1116, 989, 835, 812, 635cm> Ib-226 mp 87-88 ° C; Ή NMR (CDCl 3) δ 0.91-1.09 (m, 2H), 1.13-1.36 (m, 4H), 1.40-1.92 (m, 5H), 1.79 (s, 3H), 1.82 (s, 3H), 2.22 (s) 2.26 (s, 3H), 2.98 (d, J = 6.6 Hz, 2H), 4.87 (d, J = 7.2 Hz, 2H), 5.57 (m, 1H), 6.32-6.46 (m, 2H) 6.80 (d, J = 8.4 Hz, 1H), 7.04 (t, J = 8.4 Hz, 1H), 7.10 (s, 1H), 7.12 (s, 1H), 7.59 (dd, J = 8.4, 2.4 Hz), 1 H), 8.17 (d, J = 2.4 Hz, 1 H) IR (KBr): 3444, 1628, 1603, 1573, 1524, 1481, 1459, 1358, 1278, 1242, 1168, 1117, 1006, 974.825 cm ^-1 . Ib-227 mp 76-77 ° C; 1 H NMR (CDCl 3) δ 1.55 (s, 3H), 1.71 (s, 3H), 1.79 (s, 3H), 1.82 (s, 3H), 2.19 (s, 3H), 2.28 (s, 3H), 2.80 (d, J = 5.4 Hz, 3H), 4.20 (q, J = 5.4 Hz, 1H), 4.27 (d, J = 7.2 Hz, 2H), 4.87 (d, J = 7.2Hz, 2H), 5.29 (m, 1 H), 5.57 (m, 1 H), 6.82 (d, J = 8.1 Hz, 1 H), 7.13 (s, 2 H), 7.16-7.31 (m, 3 H), 7.59 ( dd, J = 8.1, 2.4 Hz, 1H), 8.17 (d, J = 2.4 Hz, 1H) IR (KBr): 3314, 1605, 1562, 1514, 1481, 1346, 1328, 1307, 1283, 1154, 1125, 1072, 1003, 854, 831, 703, 666 ^cm-1 Ib-228 foam; Δ NMR (CDCl 3) δ 1.00-1.74 (m, 11 H), 1.79 (s, 3 H), 1.82 (s, 3 H), 2.13 (s, 3 H), 2.27 (s, 3 H), 2.98 (d, J = 6.6) Hz, 2H), 4.87 (d, J = 6.9 Hz, 2H), 5.545.60 (m, 1H), 6.53 (dd, J = 2.4, 8.1Hz, 1H), 6.68 (d, J = 2.7 Hz, 1H) ), 6.80 (d, J = 7.8 Hz, 1H), 7.01 (d, J = 8.4 Hz, 1H), 7.06 (s, 1H), 7.60 (dd, J = 2.4, 8.4 Hz) 1 H, 8.18 (d, J = 2.1 Hz, 1 H) IR (KBr): 3413, 2926, 2853, 1607, 1517, 1479, 1449, 1376, 1281, 1240, 1033, 977 cm ^-1 . Ib-229 mp 110-112 ° C; Δ NMR (CDCl 3) δ 1.17-1.79 (m, 8H), 1.79 (s, 3H), 1.82 (s, 3H), 2.07-2.14 (m, 2H), 2.14 (s, 3H), 2.26 (s, 3H) 3.23-3.30 (m, 1H), 3.73 (br s, 1H), 4.87 (d, J = 6.9Hz, 2H), 5.54-5.60 (m, 1H), 6.52 (dd, J = 2.1, 8.1Hz) (1H), 6.68 (d, J = 2.7 Hz, 1H), 6.80 (d, J = 8.7 Hz, 1H), 7.01 (d, J = 8.4 Hz, 1H), 7.06 (s, 1H); (s, 1H), 7.60 (dd, J = 2.7, 8.7 Hz, 1H), 8.18 (d, J = 1.8 Hz, 1H) IR (KBr): 3411, 3310, 2926, 2852, 1607, 1517, 1479, 1376, 1357, 1302, 1284, 1241, 1013, 980 cm ^-1

204 ftft ftft ftft ftft ftft ft ft ft ft ft ft ft ft ft ft ft ft ft ft ft ft ft ft ft

Table 110

Ib-230 bt oil, 1 H NMR (CDCl 3) δ 1.74 (s, 3H), 1.78 (s, 3H), 1.79 (s, 3H), 1.82 (s, 3H), 2.14 (s, 3H), 2.27 (s, 3H) 3.71 (d, J = 6.6Hz, 2H); 4.87 (d, J = 6.9Hz, 2H); 5.33-5.37 (m, 1H); 5.55-5.60 (m. 1H); 6.55 (dd, J = 2.4); 6.71 (d, J = 2.4 Hz, 1H), 6.81 (d, J = 8.7 Hz, 1H), 7.03 (d, J = 8.1 Hz, 1H), 7.06 (s, 1H), 7.09 (s, 1 H), 7.61 (dd, J = 2.7, 8.7 Hz, 1 H), 8.18 (d, J = 2.4 Hz, 1 H) IR (CDCl 3): 3017, 2975, 1607, 1517, 1479, 1378, 1358 , 1282, 1240, 1227, 1220, 977 cm · Ib-231 mp 137-139 ° C; Δ NMR (CDCl 3) δ 1.05-1.80 (m, 8H), 1.79 (s, 3H), 1.82 (s, 3H), 2.05-2.12 (m, 2H), 2.22 (s, 3H), 2.26 (s, 3H) 3.22-3.30 (m, 1H), 3.75 (br s, 1H), 4.87 (d, J = 7.2 Hz, 2H), 5.54-5.60 (m, 1H), 6.34-6.44 (m, 2H), 6.81 (d, J = 9.0 Hz, 1H), 7.03 (d, J = 8.4 Hz, 1H), 7.10 (s, 1 H), 7.12 (s, 1 H), 7.59 (dd, J = 2.4, 8.4 Hz, 1 H), 8.17 ( d, J = 2.7 Hz, 1 H) IR (KBr): 3331, 2924, 2852, 1628, 1605, 1526, 1481, 1452, 1425, 1375, 1334, 1302, 1283, 1241, 1176, 1114, 1016, 986 cm ' Ib-232 mp 108-109 ° C; Δ NMR (CDCl 3) δ 1.48-1.78 (m, 6H), 1.79 (s, 3H), 1.82 (s, 3H), 2.00-2.09 (m, 2H), 2.22 (s, 3H), 2.26 (s, 3H) 3.87-3.83 (m, 1 H), 3.843.90 (m, 1 H), 4.87 (d, J = 7.2 Hz, 2 H), 5.54-5.60 (m, 1 H), 6.35-6.45 (m, 2 H), 6.80 (d, J = 8.4Hz, 1 H), 7.04 (t, J = 8.4Hz, 1 H), 7.10 (s, 1H), 7.12 (s, 1 H), 7.59 (dd, J = 2.7, 8.4Hz, 1 H) ), 8.17 (dd, J = 0.6, 2.4 Hz, 1H) IR (KBr): 3328, 2955, 2866, 1627, 1605, 1526, 1481, 1423, 1394, 1356, 1337, 1283, 1240, 1176, 1116, 1016,974 cm ' Ib-233 m.p. 77-79 [deg.] C .; Δ NMR (CDCl 3) δ 1.00 (d, J = 0.6 Hz, 3H), 1.02 (d, J = 0.6 Hz, 3H), 1.79 (s, 3 H), 1.82 (s, 3 H), 1.86-1.99 (m, 1H), 2.22 (s, 3H), 2.24 (d, J = 13.2Hz, 2H), 3.90 (br s, 1H), 4.87 (d, J = 6.6Hz, 2H), 5.54; -5.60 (m, 1 H), 6.34-6.50 (m, 2 H), 6.81 (d, J = 8.7 Hz, 1 H), 7.05 (t, J = 8.4 Hz, 1 H), 7.10 (s, 1 H), 7.12 ( s, 1H), 7.59-7.61 (m, 1 H), 8.16-8.17 (m, 1 H) IR (KBr): 3340, 2958, 2928, 2866, 1627, 1606, 1530, 1481, 1395, 1358, 1337, 1284 , 1241, 1178, 1115, 1046, 991 cm ' Ib-234 mp 109-111 ° C; Ή NMR (CDCl 3) δ 1.25 (t, J = 7.2 Hz, 3H), 1.78 (s, 3H), 1.82 (s, 3H), 2.22 (s, 3H), 2.26 (s, 3H), 2.62-2.70 ( m, 2H), 4.19 (br s, 1 H), 4.31 (s, 1 H), 4.84 (d, J = 6.6 Hz, 2 H), 5.54-5.60 (m, 1 H), 6.39-6.50 (m, 2 H), 6.81 (d, J = 9.0 Hz, 1H), 7.06 (t, J = 8.4 Hz, 1H), 7.10 (s, 1H); 7.12 (s, 1H), 7.21 (d, J = 8.1 Hz, 2H), 7.32 (d, J = 8.1 Hz, 2H), 7.59 (dd, J = 2.7, 8.4 Hz, 1H), 8.17 (d, J) IR (KBr): 3286, 2967, 2927, 2871, 1628, 1598, 1529, 1481, 1469, 1376, 1356, 1336, 1274, 1237, 1173, 1149, 1121, 1003, 975 cm -1; Ib-235 b. t. oil, Ή NMR (CDCl 3) δ 1.26 (s, 3H), 1.27 (s, 3H), 1.79 (s, 3H), 1.82 (s, 3H) ,; 2.22 (s, 3H), 2.87-2.99 (m, 1 H), 4.31 (s, 2 H), 4.87 (d, J = 7.5 Hz, 2H), 5.55-5.60 (m, 1 H) 6.40-6.51 (m, 2H); 6.81 (d, J = 8.7Hz, 1H); 7.07 (t, J = 8.4Hz, 1H); 7.10 (s, 1H); 7.12 (s, 1H); 7.17 ( d, J = 8.1 Hz, 2H), 7.33 (d, J = 8.1 Hz, 2H), 7.57-7.61 (m, IH), 8.16-8.18 (m, IH) IR (CDCl3): 3010, 2964, 1628, 1603, 1523, 1480, 1357, 1282, 1241, 977 cm -1 Ib-236 mp 203-204 ° C; Δ NMR (CDCl 3) δ 1.73 (s, 3H), 1.75 (s, 3H), 2.19 (s, 3H), 2.21 (s, 3H), 4.39 (d, J = 4.5 Hz, 2H), 4.81 (d, J = 6.9Hz, 2H), 5.47-5.52 (m, 1H), 6.48-6.49 (m, 1H), 6.62 (d, J = 8.4Hz, 2H), 6.85 (d, J = 8.4Hz, 1H), 7.05-7.09 (m, 4H), 7.50 (d, J = 8.1 Hz, 2H), 7.71 (dd, J = 2.4 Hz, 8.7Hz, 1H), 7.92 (d, J = 8.1 Hz, 2H), 8.13 (d) IR (KBr): 3422, 3004, 1686, 1609, 1523, 1482, 1423, 1392, 1377, 1356, 1283, 1240, 1182, 1124, 977 cm -1.

• · *

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Table 111

Ib-237 mp 144-147 ° C; Δ NMR (CDCl 3) δ 1.79 (s, 3H), 1.82 (s, 3H), 2.26 (s, 3H), 2.29 (s, 3H), 3.92 (s, 3H), 4.46 (s, 3H), 4.46 ( s, 2H), 4.87 (d, J = 7.2 Hz, 2H), 5.54-5.60 (m, 1H), 6.65-6.70 (m, 2H), 6.76 (d, J = 8.4 Hz, 2H), 7.17-7.21 (m, 2H), 7.47-7.50 (m, 2H), 7.59 (dd, J = 2.7, 8.4 Hz, 2H), 8.01-8.05 (m, 2H), 8.16 (d, J = 2.7 Hz, 1H) IR (KBr): 3366, 2951, 1709, 1609, 1523, 1478, 1469, 1437, 1313, 1282, 1235, 1180, 1115, 1105, 1019, 987 cm @ -1. Ib-238 m.p. 75-76 ° C; Δ NMR (CDCl 3) δ 1.74 (s, 3H), 1.77 (s, 3H), 1.79 (s, 3H), 1.82 (s, 3H), 2.06 (s, 3H), 2.08 (s, 3H), 2.25 ( s, 3H), 3.72 (d, J = 6.9 Hz, 2H), 4.87 (d, J = 6.9 Hz, 2H), 5.35-5.60 (m, 2H), 6.49-6.55 (m, 2H), 6.79-7.08 (m, 4H), 7.60 (dd, J = 2.7, 8.4 Hz, 1H), 8.18 (dd, J = 0.9, 2.7 Hz, 1H) IR (KBr): 3331, 2965, 2916, 1610, 1522, 1480, 1449, 1393, 1302, 1283, 1251, 1240, 977 cm · Ib-239 mp 87-89 ° C; Δ NMR (CDCl 3) δ 1.79 (s, 3H), 1.82 (s, 3H), 2.27 (m, 3H), 2.30 (s, 3H), 3.82 (d, J = 5.4 Hz, 2H), 4.87 (d, J = 6.9Hz, 2H), 5.18-5.36 (m, 2H), 5.54-5.60 (m, 1 H), 5.93-6.06 (m, 1 H), 6.66-6.71 (m, 2 H), 6.80 (d, J = 8.7Hz, 1H), 7.17 (dd, J), 7.15 (s, 1H), 7.17 (dd, J = 0.6), 7.17-7.22 (m, 2H), 7.58 (dd, J = 2.4) IR (KBr): 3330, 3007, 2973, 2855, 1610, 1526, 1481, 1470, 1392, 1376, 1354, 1299, 1283, 1266, 1240, 1129, 1019, 988 cm -1; Ib-240 mp 113-114 ° C; Δ NMR (CDCl 3) δ 1.79 (s, 3H), 1.82 (s, 3H), 2.25-2.27 (m, 4H), 2.29 (s, 3H), 3.99 (d, J = 2.4 Hz, 2H), 4.87 ( d, J = 5.1 Hz, 2H), 5.50-5.60 (m, 1 H), 6.73-6.78 (m, 2 H), 6.81 (dd, J = 0.6, 8.4 Hz, 1 H), 7.09 (s, 1 H), 7.15 (s, 1H), 7.21-7.25 (m, 2H), 7.59 (dd, J = 2.7, 8.4Hz, 1 H), 8.17 (dd, J = 0.6, 2.4Hz, 1 H) IR (KBr): 3311, 3271 , 2974, 2924, 1609, 1525, 1481, 1392, 1377, 1352, 1320, 1300, 1283, 1265, 1239, 1182, 1121, 987 cm &lt; -1 &gt; Ib-241 mp 125-126 ° C; Δ NMR (CDCl 3) δ 0.94-1.87 (m, 11H), 1.78 (s, 3H), 1.82 (s, 3H), 2.26 (s, 3H), 2.30 (s, 3H), 3.00 (d, J = 6.6) Hz, 2H), 4.87 (d, J = 6.9 Hz, 2H), 5.54-5.60 (m, 1H), 6.60-6.67 (m, 2H), 6.81 (d, J = 8.4 Hz, 1H), 7.09 (s) (1H), 7.15 (s, 1H), 7.16-7.21 (m, 2H), 7.58 (dd, J = 2.4, 8.4Hz, 1H), 8.17 (dd, J = 0.6, 2.1Hz, 1 H) IR (KBr): 3356, 2919, 2851, 1613, 1528, 1482, 1470, 1447, 1395, 1355, 1325, 1299, 1284, 1262, 1241, 1182, 1020, 985 cm? ' Ib-242 b. 1.173-175 ° C; Δ NMR (CDCl 3) δ 1.14-1.787 (m, 8H), 1.78 (s, 3H), 1.81 (s, 3H), 2.08-2.12 (m, 2H), 2.27 (s, 3H), 2.30 (s, 3H) 3.26-3.34 (m, 1H); 4.87 (d, 1H); J = 7.2Hz, 2H), 5.54-5.60 (m, 1 H), 6.62-6.67 (m, 2 H), 6.81 (dd, J = 0.6, 8.4Hz, 1 H), 7.09 (s, 1 H), 7.15 (s) (1H), 7.15-7.19 (m, 2H), 7.58 (dd, J = 2.4, 8.7Hz, 1 H), 8.16 (dd, J = 0.6, 2.4Hz, 1 H) IR (KBr): 3326, 2922, 2852 , 1611, 1523, 1482, 1452, 1393, 1354, 1319, 1300, 1282, 1239, 1182, 1125, 983 cm · Ib-243 mp 141-142 ° C; Δ NMR (CDCl 3) δ 1.78 (s, 3H), 1.82 (s, 3H), 2.26 (s, 3H), 2.28 (s, 3H), 4.27 (br s, 1H), 4.43 (br s, 2H), 4.87 (d, J = 7.2 Hz, 2H), 5.545.60 (m, 1H), 6.63-6.66 (m, 2H), 6.81 (d, J = 8.4 Hz, 1H), 7.09 (s, 1H), 7.13 (s, 1H), 7.17-7.20 (m, 2H), 7.33-7.35 (m, 2H), 7.57 (dd, J = 2.1,8.4 Hz, 1H), 8.16 (d, J = 2.4 Hz, 1H), 8.57-8.59 (m, 2H); IR (KBr): 3279, 2972, 2925, 1603, 1522, 1479, 1459, 1418, 1375, 1351, 1318, 1282, 1272, 1240, 1179, 1120, 1001, cm @ -1.

206 · • € € € € € € € € € ^{c c c c c c c c c c c}

Table 112

Ib-244 m.p. 123-125 [deg.] C .; Δ NMR (CDCl 3) δ 1.78 (s, 3H), 1.82 (s, 3H), 2.26 (s, 3H), 2.29 (s, 3H), 4.38 (s, 2H), 4.87 (d, J = 6.9Hz, 2H), 5.54-5.60 (m, 1 H), 6.696.73 (m, 2 H), 6.81 (dd, J = 0.6, 8.4Hz, 1 H), 7.09 (s, 1 H), 7.14 (s, 1 H), 7.177 .22 (m, 2H), 7.26-7.44 (m, 5H), 7.58 (dd, J = 2.4, 8.4 Hz, 1H), 8.16 (d, J = 1.8 Hz, 1H) IR (KBr): 3348, 2966; , 2921, 1613, 1527, 1482, 1469, 1453, 1394, 1356, 1326, 1297, 1285, 1264, 1241, 1020, 987 cm » Ib-245 mp 137-138 ° C; @ 1 H NMR (CDCl3) .delta. 1.79 (s, 3H), 1.82 (s, 3H), 2.28 (s, 6H), 3.33 (s, 3H), 4.55 (br s, 2H), 4.87 (d, J = 7.2) Hz, 2H), 5.54-5.60 (m, 1 H), 6.81 (dd, J = 0.6, 8.7Hz, 1 H), 7.12-7.14 (m, 2 H), 7.35-7.39 (m, 2 H), 7.44-7.49 ( m, 2H), 7.59 (dd, J = 2.4, 8.4 Hz, 1H), 8.17 (dd, J = 0.6, 2.4 Hz, 1H), IR (KBr): 3376, 3284, 2972, 2922, 1604, 1480, 1462, 1342, 1281, 1180, 1140, 999 cm ¹ Ib-246 b. 1118-120 ° C; @ 1 H NMR (CDCl3) .delta. 1.78 (s, 3H), 1.87 (s, 3H), 2.26 (s, 3H), 2.30 (s, 3H), 4.39 (s, 2H), 4.87 (d, J = 7.2 Hz) (2H), 5.54-5.60 (m, 1 H), 6.706.73 (m, 2 H), 6.80 (d, J = 8.4 Hz, 1 H), 7.10-7.14 (m, 3 H), 7.15-7.24 (m, 3 H) 7.39 (dd, J = 3.0, 5.1Hz, 1 H), 7.59 (dd, J = 2.4, 8.4Hz, 1 H), 8.17 (d, J = 1.8 Hz, 1 H) IR (KBr): 3397, 2973, 2920, 2851, 1610, 1522, 1480, 1470, 1376, 1350, 1298, 1280, 1260, 1235, 1182, 1122, 980 cm- » Ib-247 mp 112-115 ° C; @ 1 H NMR (CDCl3) .delta. 1.79 (s, 3H), 1.82 (s, 3H), 2.27 (s, 3H), 2.30 (s, 3H), 4.22 (s, 2H), 4.87 (d, J = 6.9 Hz) (2H), 5.55-5.60 (m, 1 H), 6.446.45 (m, 1 H), 6.70-6.74 (m, 2 H), 6.81 (dd, J = 0.9, 8.4Hz, 1 H), 7.09 (s, 1H) 7.17 (dd, J = 2.4, 8.7Hz, 1H), 8.17 (dd, J = 0.6, 2.4), 7.15-7.23 (m, 1H), 7.41-7.45 (m, 1H); Hz, 1H), IR (KBr): 3338, 2924, 1613, 1526, 1501, 1482, 1471, 1394, 1355, 1317, 1298, 1285, 1241, 1156, 1020, 977 cm @ -1 » Ib-248 mp 123-125 ° C; @ 1 H NMR (CDCl3) .delta. 1.78 (s, 3H), 1.81 (s, 3H), 2.27 (s, 3H), 2.29 (s, 3H), 2.60 (br s, 3H), 4.87 (d, J = 7.2) Hz, 2H), 5.54-5.60 (m, 1 H), 6.73-6.77 (m, 2 H), 6.81 (d, J = 8.4 Hz, 1 H), 7.09 (s, 1 H), 7.14 (s, 1 H), 7.147 18 (m, 2H), 7.59 (dd, J = 2.4, 8.4 Hz, 1H), 8.17 (d, J = 2.4 Hz, 1H), IR (KBr) 3449, 3341, 2972, 2925, 1623, 1604 , 1521, 1481, 1394, 1359, 1281, 1241, 1128, 984 cm » Ib-249 m.p. 70-72 ° C; @ 1 H NMR (CDCl3) .delta. 1.79 (s, 3H), 1.82 (s, 3H), 2.27 (s, 3H), 2.30 (s, 3H), 2.89 (s, 3H), 4.87 (d, J = 7.2 Hz) (2H), 5.55-5.60 (m, 1 H), 6.66-6.71 (m, 2 H), 6.81 (dd, J = 0.9, 8.4Hz, 1 H), 7.09 (s, 1 H), 7.15 (s, 1 H), 7.19-7.23 (m, 2H), 7.59 (dd, J = 2.7, 8.4 Hz, 1H), 8.17 (dd, J = 0.6, 2.4 Hz, 1H), IR (KBr): 3356, 2923, 2883, 1614, 1603, 1529, 1482, 1393, 1357, 1320, 1298, 1282, 1264, 1241, 1182, 981 cm » lb-250 mp 87-88 ° C; @ 1 H NMR (CDCl3) .delta. 1.74 (s, 3H), 1.78 (s, 3H), 1.79 (s, 3H), 1.80 (s, 3H), 2.22 (s, 3H), 2.26 (s, 3H), 3.71 (d, J = 6.9 Hz, 2H), 4.87 (d, J = 7.2 Hz, 2H), 5.32-5.37 (m, 1H), 5.55-5.60 (m, 1H), 6.35-6.47 (m, 2H), 6.81 (dd, J = 0.6, 8.4Hz, 1 H), 7.02-7.13 (m, 3H), 7.59 (dd, J = 2.4, 8.4Hz, 1 H), 8.16 (dd, J = 0.9, 5.7Hz, 1 H) , IR (Nujol): 3330, 2923, 2853, 1627, 1606, 1564, 1527, 1481, 1471, 1395, 1376, 1357, 1337, 1284, 1240, 1178, 1116, 990 cm »

• 2D7 ·

Table 113

Ib-251 mp 102-103 ° C; Δ NMR (CDCl 3) δ 1.75 (s, 3H), 1.79 (s, 6H), 1.82 (s, 3H), 2.19 (s, 3H), 2.27 (s, 3H), 2.31 (s, 3H), 3.49 ( br s, 1H), 3.78 (d, J = 6.9 Hz, 2H), 4.87 (d, J = 6.9 Hz, 2H), 5.42 (t, J = 6.9 Hz, 2H), 5.57 (t, J = 7.2 Hz) (1H), 6.68 (d, J = 8.1 Hz, 1H), 6.80 (d, J = 8.4 Hz, 1H), 7.09 (s, 2H), 7.13-7.17 (m, 2H), 7.59 (dd, J = 2.7, 8.4Hz, 1H); 8.17 (d, J = 2.4Hz, 1H); IR (KBr): 3363, 2969, 2918, 2884, 2854, 1609, 1601, 1517, 1482, 1468, 1442, 1378, 1283, 1250, 981, 891 cm @ -1. Ib-252 m.p. 109-110 [deg.] C .; Δ NMR (CDCl 3) δ 1.79 (s, 3H), 1.82 (s, 3H), 2.23 (s, 3H), 2.27 (s, 3H), 2.30 (s, 3H), 3.85 (s, 3H), 4.42 (s, 2H), 4.87 (d, J = 7.2 Hz, 2H), 5.57 (t, J = 6.6 Hz, 1H), 6.69 (d, J = 8.1 Hz, 1H), 7.09-7.15 (m, 4H) 7.31-7.44 (m, 5H), 7.59 (dd, J = 2.4, 8.7 Hz, 1H), 8.17 (d, J = 1.5 Hz, 1H); IR (KBr): 3431, 3351, 2970, 2919, 2854, 1602, 1517, 1483, 1466, 1451, 1377, 1285, 1250, 1132, 975, 836 cm &lt; -1 &gt;. Ib-253 mp 72-73 ° C; 1 H NMR (CDCl 3) δ 1.75 (s, 3H), 1.79 (s, 6H), 1.82 (s, 3H), 2.27 (s, 3H), 2.30 (s, 3H), 3.77 (d, J = 6.9Hz) (2H), 3.92 (br, 1H), 4.87 (d, J = 7.2 Hz, 2H), 5.38 (t, J = 6.9 Hz, 1H), 5.57 (t, J = 6.9 Hz, 1H), 6.74 ( dd, J = 8.1, 8.7Hz, 1 H, 6.81 (dd, J = 0.9, 6.3Hz, 1 H), 6.99-7.00 (m, 1 H), 7.00 (s, 1 H), 7.03 (s, 1 H), 7.14 (s, 1H), 7.58 (dd, J = 2.7, 8.7 Hz, 1H), 8.16 (d, J = 2.7 Hz, 1H); IR (KBr) 3431, 2971, 2915, 1624, 1599, 1528, 1479, 1465, 1335, 1241, 1122,987, 833 cm @ -1. Ib-254 m.p. 106-107; Δ NMR (CDCl 3) δ 1.79 (s, 3H), 1.82 (s, 3H), 2.26 (s, 3H), 2.29 (s, 3H), 4.42 (s, 2H), 3.85 (s, 3H), 4.87 (d, J = 7.2 Hz, 2H), 6.81 (d, J = 8.4 Hz, 1H), 6.73 (dd, J = 8.7 Hz, 1H), 6.83 (dd, J = 8.4 Hz, 1H), 6.96 -6.99 (m, 1 H), 7.03 (d, J = 12.9 Hz, 1 H), 7.10 (d, J = 9.9 Hz, 2 H), 7.26-7.43 (m, 5 H), 7.58 (dd, J = 2.4, 8.4) Hz, 1H), 8.16 (d, J = 1.8 Hz, 1H); IR (KBr): 3428, 2922, 2857, 1623, 1601, 1566, 1500, 1427, 1391, 1376, 1308, 1298, 1149, 1134, 1074, 1038, 1018, 927, 895 cm &lt; -1 &gt;. Ib-255 mp 83-84 ° C; Δ NMR (CDCl 3) δ 1.75 (s, 3H), 1.79 (s, 6H), 1.82 (s, 3H), 2.27 (s, 3H), 2.30 (s, 3H), 3.79 (d, J = 6.3 H): z, 2H), 4.29 (brs, 1H), 4.87 (d, J = 7.2 Hz, 2H), 5.39 (t, J = 6.6 Hz, 1H), 5.57 (t, J = 7.2 Hz, 1H), 6.71 (d, J = 8.7 Hz, 1H), 6.81 (d, J = 8.1 Hz, 1H), 7.10 (s, 1H), 7.13 (s, 1H), 7.16 (dd, J = 2.1, 8.4Hz, 1H) 7.27 (dd, J = 2.1, 7.5Hz, 1 H), 7.58 (dd, J = 2.7, 8.7Hz, 1 H), 8.16 (d, J = 1.8Hz, 1 H); IR (KBr): 3420, 3356, 2968, 2924, 1603, 1520, 1482, 1468, 1284, 1248, 1078, 981, 838 cm &lt; -1 &gt;. Ib-256 mp 89-90 ° C; Δ NMR (CDCl 3) δ 1.79 (s, 3H), 1.82 (s, 3H), 2.26 (s, 3H), 2.29 (s, 3H), 4.46 (s, 2H), 4.79 (s, 3H), 4.87 (d, J = 6.9 Hz, 2H), 6.69 (d, J = 8.1 Hz, 1H), 6.89 (d, J = 8.7 Hz, 1H), 7.09-7.13 (m, 3H), 7.31-7.43 (m, 6H), 7.58 (dd, J = 2.7, 8.7 Hz, 1H), 8.16 (d, J = 2.4 Hz, 1H); IR (KBr): 3422, 3340, 2975, 2923, 1604, 1520, 1482, 1455, 1286, 1248, 975.887 cm · ¹ . Ib-257 mp 62-63 ° C; @ 1 H NMR (CDCl3) .delta. 1.74 (s, 3H), 1.78 (s, 3H), 1.79 (s, 3H), 1.82 (s, 3H), 2.28 (s, 3H), 2.32 (s, 3H), 3.76 (d, J = 6.6 Hz, 2H), 3.86 (s, 3H), 4.27 (br s, 1H), 4.87 (d, J = 6.9 Hz, 2H), 5.41 (t, J = 6.6 Hz, 1H), 5.58 (t, J = 6.9 Hz, 1H), 6.67 (d, J = 8.1 Hz, 1H), 6.78-6.79 (m, 2H), 6.88 (dd, J = 1.8, 8.1 Hz, 1H), 7.11 (s) 1 H, 7.18 (s, 1 H), 7.59 (dd, J = 2.4, 8.4 Hz, 1 H), 8.17 (d, J = 1.8 Hz, 1 H); IR (KBr): 3437, 2880, 2856, 1560, 1416, 1378, 1306, 1176, 1075, 1017, 948, 898, 883 cm @ -1.

• · ·

2-8 ’·

Table 114

Ib-258 mp 86-87 ° C; Δ NMR (CDCl 3) δ 1.79 (s, 3H), 1.82 (s, 3H), 2.27 (s, 3H), 3.31 (s, 3H), 3.87 (s, 3H), 4.40 (s, 2H), 4.67 ( br s, 1H), 4.87 (d, J = 6.9 Hz, 2H), 5.57 (t, J = 7.2 Hz, 1H), 6.65 (d, J = 7.8 Hz, 1H), 6.79-6.86 (m, 3H) 7.10 (s, 1H); 7.17 (s, 1H); 7.31-7.44 (m, 5H); 7.59 (dd, J = 2.4, 8.7 Hz, 1H); 8.17 (d, J = 2.4 Hz, 1H); IR (KBr): 3426, 2948, 2914, 2857, 1600, 1561, 1525, 1415, 1304, 1177, 1018, 948, 900, 883 cm &^lt; -1 ^&gt;. Ib-259 mp 108-109 ° C; Ή NMR (CDCl 3) δ 1.74 (s, 3H), 1.77 (s, 3H), 1.79 (s, 3H), 1.82 (s, 3H), 2.27 (s, 3H), 2.31 (s, 3H), 3.66 ( br s, 1H), 3.74 (d, J = 6.8Hz, 2H), 4.87 (d, J = 7.1Hz, 2H), 5.38 (br t, J = 6.8Hz, 1H), 5.58 (brt, J = 7.1 Hz, 1H), 6.67 (d, J = 8.5Hz, 2H), 6.81 (dd, J = 0.7, 8.6Hz, 1H), 7.10 (s, 1H), 7.15 (s, 1 H), 7.20 (d, J = 8.5 Hz, 2 H), 7.59 (dd, J = 2.4, 8.6 Hz, 1 H) 8.17 (dd, J = 0.7, 2.4 Hz, 1 H) Ib-260 mp 74-75 ° C; Δ NMR (CDCl 3) δ 1.72 (s, 3H), 1.77 (s, 3H), 1.81 (s, 6H), 2.29 (s, 3H), 2.31 (s, 3H), 3.76 (d, 2H, J = 6.9) Hz), 5.07 (d, J = 7.2 Hz, 2H), 5.39 (m, 1H), 5.58 (m, 1H), 6.77 (d, J = 7.8 Hz, 2H), 7.11-7.23 (m, 5H), 8.26 (d, J = 2.1 Hz, 1H); 8.40 (d, J = 2.1 Hz, 2H); IR (CHCl3): 3426, 2975, 2918, 2862, 1612, 1556, 1528, 1498, 1471, 1379, 1354, 1299, 1241, 12256, 1185, 1091, 970, 947 cm @ ^-1 Ib-261 Δ NMR (DMSO) δ 1.73 (s, 3H), 1.76 (s, 3H), 2.22 (s, 3H), 2.23 (s, 3H), 4.82 (d, J = 6.9 Hz, 2H), 5.50 (t, J = 6.9 Hz 1H), 6.86 (d, J = 8.4 Hz, 1H), 6.967.05 (m, 2H), 7.11-7.17 (m, 3H), 7.72 (dd, J = 2.7, 8.7 Hz, 1H) 8.15 (d, J = 2.7 Hz, 1 H), 9.94 (brs, 1 H); IR (neat): 3350, 2964, 1601, 1520, 1480, 1377, 1355, 1283, 1241, 1113, 979, 755 cm ^&lt; -1 ^&gt; Ib-262 mp 96 ° C 1 H NMR (DMSO) δ 1.74 (s, 6H), 1.76 (s, 3H), 1.77 (s, 3H), 2.22 (s, 3H), 2.34 (s, 3H), 4.65 (d, J = 6.9Hz, 2H); 4.82 (d, J = 6.6Hz, 2H); 5.44-5.54 (m, 2H); 7.10-7.18 (m, 3H); 7.21-7.27 (m, 2H); 7.73 (dd) J = 2.4, 8.4Hz, 1H), 8.15 (d, J = 2.4Hz, 1H); IR (nujol): 1600, 1517, 1280, 1269, 1127, 995, 836 cm ^&lt; -1 ^&gt;. Ib-263 mp 78-79 ° C Ή NMR (CD 3 OD) δ 1.79 (s, 3H), 1.80 (s, 3H), 2.42 (s, 6H), 3.92 (s, 3H), 4.83 (d, J = 7.0 Hz, 2H) ), 5.50-5.56 (m, 1 H), 6.84 (dd, J = 0.6, 8.7 Hz, 1H), 7.05-7.18 (m, 5 H), 7.67 (dd, J = 2.7, 8.7 Hz, 1H), 8.07 ( dd, J = 2.7, 0.6 Hz, 1H); IR (nujol): 1600, 1577, 1280, 1270, 1127, 983, 838 cm ^&lt; -1 ^&gt;. Ib-264 mp 80-81 ° C Ή NMR (CDCl 3) δ 1.79 (s, 3H), 1.82 (s, 3H), 2.72 (s, 6H), 4.88 (d, J = 7.2 Hz, 2H), 5.13 (s, 2H) ), 5.55-5.60 (m, 1H), 6.40 (dd, J = 1.5Hz, 1H), 6.48 (d, J = 3.6Hz, 1H), 6.82 (d, J = 8.4Hz, 1H), 7.02 -7.06 (m, 1 H), 7.08-7.16 (m, 4 H), 7.47-7.48 (m, 1 H), 7.58 (dd, J = 2.7, 8.4 Hz, 1 H) 8.16 (d, J = 2.7 Hz, 1 H) ; IR (nujol): 1601, 1518, 1281, 1125, 984, 834 cm ^&lt; -1 ^&gt;. Ib-265 b. 1.105 DEG C. @ 1 H NMR (CDCl3) .delta. 1.79 (s, 3H), 1.82 (s, 3H), 2.27 (s, 6H), 4.88 (d, J = 7.2 Hz, 2H), 5.20 (s, 2H) 5.50-5.60 (m, 1 H), 6.81 (d, J = 8.4 Hz, 1 H), 7.00-7.15 (m, 5 H), 7.32-7.50 (m, 5 H), 7.58 (dd, J = 2.4.8.4 Hz) (1H) 8.16 (d, J = 2.4Hz, 1H); IR (nujol): 1602, 1299, 1276, 1128, 974, 749 cm @ -1. Ib-266 b. 1.188-190 ° C; @ 1 H NMR (CDCl3) .delta. 1.79 (s, 3H), 1.82 (s, 3H), 2.27 (s, 3H), 2.29 (s, 3H), 4.88 (d, J = 7.1Hz, 2H), 4.89 (s) (2H), 5.58 (t, J = 7.1Hz, 2H), 6.83 (dd, J = 8.4, 0.6Hz, 1H), 7.13 (s, 1H), 7.15 (s, 1H), 7.50-7.55 ( m, 2H), 7.59 (dd, J = 8.4, 2.4 Hz, 1H), 7.97-8.02 (m, 2H), 8.16 (dd, J = 2.4, 0.6 Hz, 1H); IR (KBr): 3367, 3321, 3271, 1602, 1479, 1333, 1281, 1163, 1153, 995, 980, 785, 607, 553 cm @ -1.

• · · · · · · · · · · · · ·

Table 115

Ib-267 mp 176-178 ° C; Δ NMR (CDCl 3) δ 1.79 (s, 3H), 1.82 (s, 3H), 2.19 (s, 3H), 2.28 (s, 3H), 4.88 (d, J = 6.9Hz, 2H), 4.96 (s, 2H), 5.57 (t, J = 7.1Hz, 2H), 6.82 (dd, J = 8.4, 0.6Hz, 1H), 7.11 (s, 1H), 7.15 (s, 1H), 7.47 (t, J) = 8.1 Hz, 1H), 7.59 (dd, J = 8.4, 2.6 Hz, 1H), 7.74 (dd, J = 9.0, 1.8 Hz, 1H), 7.80 (dd, J = 8.1, 1.8 Hz, 1H), 8.16 (dd, J = 2.6, 0.6Hz, 1 H); IR (KBr): 3352, 3261, 1603, 1479, 1317, 1152, 993, 831, 777, 600 cm -1 Ib-268 oil, Ή NMR (CDCl 3) δ 1.74 (s, 3H), 1.78 (s, 3H), 1.80 (s, 3H), 1.81 (s, 3H), 2.05 (s, 3H), 2.19 (s, 3H), 2.26 (s, 3H); 3.72 (d, J = 6.6 Hz, 2H); 3.77 (br s, 1H); 4.85 (m, 2H); 5.35 (m. 1H); 5.56 (m. 1H); 6.34 ( dd, J = 2.1, 9.3 Hz, 1 H, 6.45 (dd, J = 2.1, 8.4 Hz, 1 H), 6.61 (d, J = 8.4 Hz, 1 H), 6.97 (s, 1 H), 7.07 (t, J) = 8.4 Hz, 1H), 7.34 (d, J = 8.4Hz, 1H) Ib-269 oil, Ή NMR (CDCl 3) δ 1.74 (s, 3H), 1.78 (s, 6H), 1.82 (s, 3H), 2.21 (s, 3H), 2.25 (s, 3H), 2.27 (s, 3H), 3.71 (d, J = 6.6Hz, 2H), 4.89 (d, J = 6.6Hz, 2H), 5.35 (br t, J = 6.6Hz, 1H), 5.57 (br t, J = 6.6Hz, 1H), 6.39 (dd, J = 2.1, 12.6 Hz, 1 H), 6.45 (dd, J = 2.1, 8.4 Hz, 1 H), 7.06 (t, J = 8.4 Hz, 1 H), 7.10 (s, 1 H), 7.12 (s (1H), 7.41 (d, J = 2.4Hz, 1H), 8.01 (d, J = 2.4Hz, 1H) Ib-270 oil, Ή NMR (CDCl 3) δ 1.74 (s, 3H), 1.78 (s, 6H), 1.82 (s, 3H), 2.05 (s, 3H), 2.07 (s, 3H), 2.20 (s, 3H), 3.72 (d, J = 6.6 Hz, 2H), 3.85 (d, J = 7.8 Hz, 2H), 5.36 (m, 1H), 5.56 (m, 1H), 6.39 (dd, J) = 2.4, 12.3 Hz, 1 H), 6.45 (dd, J = 2.4, 8.1 Hz, 1 H), 6.68 (s, 1 H), 6.97 (s, 1 H), 7.07 (t, J = 8.4 Hz, 1 H), 7.10 (s, 1 H), 7.93 (s, 1 H) Ib-271 oil, Ή NMR (CDCl 3) δ 1.78 (s, 3H), 1.81 (s, 3H), 2.20 (s, 3H), 2.25 (s, 3H), 2.27 (s, 3H), 4.90 (d, J = 6.6) Hz, 2H), 5.58 (br t, J = 6.9Hz, 1H), 6.47 (dd, J = 2.1, 11.4Hz, 1H), 6.53 (dd, J = 2.1, 8.1Hz, 1H), 7.05 (t, J = 8.1 Hz, 1 H), 7.10 (s, 1H), 7.11 (s, 1H), 7.41 (d, J = 2.1Hz, 1H), 8.01 (d, J = 2.1Hz, 1H) Ib-272 oil, Ή NMR (CDCl 3) δ 1.78 (s, 3H), 1.82 (s, 3H), 2.05 (s, 3H), 2.07 (s, 3H), 2.19 (s, 3H), 3.85 (s, 3H) 4.85 (d, J = 6.9Hz, 2H); 5.56 (m, 1H); 6.48 (dd, J = 2.1, 11.7 Hz, 1 H), 6.53 (dd, J = 2.1, 8.4 Hz, 1 H), 6.68 (s, 1 H), 6.98 (s, 1 H), 7.07 (t, J = 8.4 Hz, 1 H), 7.10 (s, 1 H), 7.92 (s, 1 H) Ib-273 oil, Ή NMR (CDCl 3) δ 1.74 (s, 3H), 1.77 (s, 3H), 1.805 (s, 3H), 1.810 (s, 3H), 2.06 (s, 3H), 2.26 (s, 3H), 2.28 (s, 3H), 3.74 (d, J = 6.6Hz, 2H), 4.834.87 (m, 2H), 5.38 (m, 1H), 5.56 (m, 1H), 6.61 (d, J = 8.4Hz) (1H), 6.68 (d, J = 9.0Hz, 2H), 6.96 (s, 1H), 7.21 (d, J = 9.0Hz, 2H), 7.34 (d, J = 8.4Hz, 1H) Ib-274 oil, Ή NMR (CDCl 3) δ 1.74 (s, 3H), 1.77 (s, 3H), 1.78 (s, 3H), 1.81 (s, 3H), 2.25 (s, 3H), 2.27 (s, 3H), 2.30 (s, 3H), 3.74 (d, J = 6.6Hz, 2H), 4.89 (d, J = 6.9Hz, 2H), 5.38 (m, 1H), 5.58 (m, 1H), 6.68 (d, J) = 8.7 Hz, 2H), 7.09 (s, 1 H), 7.15 (s, 1 H), 7.20 (d, J = 8.7 Hz, 2 H), 7.41 (m, 1 H), 8.01 (m, 1 H) Ib-275 oil, δ NMR (CDCl 3) δ 1.74 (s, 3H), 1.78 (s, 6H), 1.81 (s, 3H), 2.05 (s, 3H), 2.07 (s, 3H), 2.28 (s, 3H), 3.74 (d, J = 6.9Hz, 2H), 4.85 (d, J = 7.5Hz, 2H), 5.38 (m, 1H), 5.56 (m, 1H), 6.67-6.71 (m, 3H), 6.96 (s) 1 H, 7.12 (s, 1 H), 7.21 (d, J = 8.7 Hz, 1 H), 7.92 (s, 1 H) Ib-276 oil, Ή NMR (CDCl 3) δ 1.75 (s, 3H), 1.81 (s, 3H), 2.05 (s, 3H), 2.06 (s, 3H), 2.26 (s, 3H), 3.75 (br, 2H), 4.84-4.87 (m, 2 H), 5.57 (m, 1 H), 6.62 (d, J = 8.1 Hz, 1 H), 6.74-6.77 (m, 3 H), 6.96 (s, 1 H), 7.11 (s, 1 H) 7.17-7.20 (m, 2H); 7.34 (d, J = 8.1Hz, 1H);

• · · · · ·

210 ft · 9 9 9 9 9 9 9 9

9 99 99

Table 116

Ib-277 oil, Ή NMR (CDCl 3) δ 1.78 (s, 3H), 1.81 (s, 3H), 2.25 (s, 3H), 2.27 (s, 3H), 2.28 (s, 3H), 4.90 (d, J = 6.8) Hz, 2H), 5.58 (m, 1H); 6.73-6.78 (m, 2H); 7.08-7.41 (m, 5H); 8.00 (d, J = 2.2Hz, 1H); Ib-278 oil, Ή NMR (CDCl 3) δ 1.78 (s, 3H), 1.82 (s, 3H), 2.05 (s, 3H), 2.08 (s, 3H), 2.27 (s, 3H), 4.85 (d, J = 8.1) Hz, 2H), 5.57 (m, 1H), 6.68 (s, 1H), 6.75-6.78 (m, 2H), 6.97 (s, IH), 7.12 (s, IH), 7.17-7.21 (m, 2H) , 7.93 (s, IH) Ib-279 mp 102-103 ° C; Ή NMR (CDCl 3) δ 1.74 (s, 3H), 1.77 (s, 3H), 2.26 (s, 3H), 2.31 (s, 3H), 3.74 (d, J = 6.9Hz, 2H), 4.56-4.60 ( m, 1H), 4.66-4.73 (m, 2H), 4.86-4.89 (m, IH), 5.35-5.40 (m, 1H), 6.65-6.70 (m, 2H), 6.86 (d, J = 8.4 Hz, 1H), 7.09 (s, IH), 7.16 (s, IH), 7.18-7.22 (m, 2H), 7.62 (dd, J = 2.4, 8.7Hz, IH), 8.13-8.14 (m, IH), IR ( KBr): 3356, 2983, 2925, 1611, 1526, 1482, 1452, 1391, 1348, 1307, 1289, 1263, 1242, 1073, 1020 cm ^&lt; -1 ^&gt; Ib-280 mp 81-82 ° C; Δ NMR (CDCl 3) δ 2.27 (s, 3H), 2.30 (s, 3H), 3.82-3.84 (m, 2H), 4.88-4.91 (m, 2H), 5.18-5.47 (m, 4H), 5.93-6.21 (m, 2H), 6.67-6.71 (m, 2H), 6.83 (d, J = 8.4Hz, 1H), 7.09 (s, IH), 7.15 (s, IH), 7.17-7.22 (m, 2H), 7.61 (dd, J = 2.4, 7.2Hz, IH), 8.16 (dd, J = 0.9, 2.4Hz, IH) IR (KBr): 3342, 3007, 2921, 1609, 1524, 1482, 1391, 1314, 1279, 1182, 1020, 996 cm &gt;. Ib-281 mp 142-144 ° C; Δ NMR (CDCl 3) δ 2.20-2.27 (m, 4H), 2.29 (s, 3H), 2.50 (s, 1H), 3.99 (d, J = 2.4Hz, IH), 5.04 (d, J = 2.7Hz, 1H), 6.73-6.78 (m, 2H), 6.87 (dd, J = 2.4, 8.7Hz, IH), 7.10 (s, IH), 7.16 (s, IH), 7.21-7.26 (m, 2H), 7.63 (dd, J = 2.4, 8.7 Hz, IH), 8.18 (dd, J = 0.9, 2.4 Hz, IH) IR (KBr): 3360, 3292, 3266, 3005, 1608, 1523, 1479, 1438, 1391, 1299 , 1280, 1265, 1233, 1022, 1010 cm · Ib-282 mp 65-68 ° C; Ή NMR (CDCl 3) δ 1.58 (s, 3H), 1.70 (s, 3H), 1.73 (s, 3H), 1.78 (s, 3H), 2.23 (s, 3H), 2.26 (s, 3H), 2.43- 2.50 (m, 2H), 2.87 (t, J = 7.5 Hz, 2H), 3.71 (d, J = 6.9 Hz, 2H), 3.79 (br s, 1H), 5.20-5.36 (m, 2H), 6.36- 6.47 (m, 2H), 7.06 (t, J = 8.4 Hz, IH), 7.12 (s, IH), 7.14 (d, J = 7.8 Hz, IH), 7.60 (dd, J) IR (KBr): 3427, 3274, 2965, 2913, 2854, 1629, 1536, 1480, 1443, 1421, 1375, 1343, 1305. , 1276, 1245, 1173, 1115, 1023 cm ' Ib-283 m.p. 112-113 [deg.] C .; Ή NMR (CDCl 3) δ 1.69 (s, 3H), 1.70 (s, 3H), 1.73 (s, 3H), 1.77 (s, 3H), 2.22 (s, 3H), 2.23 (s, 3H), 3.83- 3.88 (m, 2H); 4.64 (d, J = 7.2 Hz, 2H); 5.28-5.33 (m, 1H); 5.46-5.51 (m, 1H); 6.50-6.61 (m, 2H); m, 3H), 7.19-7.26 (m, 2H), 7.40 (dd, J = 2.7, 8.7 Hz, 1H), 7.97 (d, J = 2.4 Hz, 1H), IR (KBr): 3222, 2971, 2922 , 2858, 1605, 1536, 1493, 1468, 1428, 1396, 1318, 1297, 1272, 1262, 1229, 1194, 1125, 1090, 996 cm &lt; -1 &gt; Ib-284 m.p. 141-143 [deg.] C .; Δ NMR (CDCl 3) δ 1.74 (s, 3H), 1.77 (s, 6H), 1.82 (s, 3H), 2.28 (s, 3H), 2.29 (s, 3H), 3.85-3.95 (m, 2H), 4.56 (d, J = 6.6 Hz, 2H), 5.36 (m, 1H), 5.54 (tm, J = 6.6 Hz, 2H), 6.45 (m, IH), 6.97 (d, J = 8.7 Hz, 2H), 7.11 (s, 1H); 7.14 (s, 1H); 7.28 (d, J = 8.7 Hz, 2H); 7.47 (m, 1H); 8.13 (m, 1H); IR (KBr) 3433, 3220, 1610, 1536, 1492, 1233, 1176, 998, 844 cm -1. Ib-285 mp 113-114 ° C; Δ NMR (DMSO-d 6) δ 1.73 (s, 3H), 1.77 (s, 3H), 2.22 (s, 6H), 4.64 (d, J = 6.9 Hz, 2H), 5.46-5.50 (m, 1H), 5.98 (s, 2H), 6.51 (d, J = 8.4 Hz, IH), 7.07-7.11 (m, 3H), 7.19-7.26 (m, 2H), 7.41 (dd, J = 2.7, 8.4Hz, IH) , 7.90 (d, J = 2.7 Hz, 1H); IR (KBr): 3456, 3292, 3173, 2917, 1631, 1617, 1521, 1485, 1442, 1395, 1378, 1298, 1268, 1232, 1193, 1126, 1004 cm '

211

Table 117

Ib-286 mp 134-136 ° C; Ή NMR (CDCl 3) δ 1.77 (s, 3H), 1.82 (s, 3H), 2.28 (s, 6H), 4.56 (d, J = 6.6Hz, 2H), 5.54 (tm, J = 6.6Hz, 1H) 6.58 (m, 1H), 6.98 (d, J = 9.0 Hz, 2H), 7.10 (s, 1H), 7.14 (s, 1H), 7.28 (d, J = 9.0 Hz, 2H), 7.48 (m, 1H), 8.10 (m, IH); IR (KBr) 3458, 3300, 3176, 1630, 1614, 1519, 1485, 1238, 1003, 837 cm ^1st Ib-287 mp 187-189 ° C; Ή NMR (CDCl 3) δ 1.15-1.54 (m, 4H), 1.58-1.86 (m, 4H), 1.77 (s, 3H), 1.82 (s, 3H), 2.02-2.15 (m, 2H), 2.28 (s) 3.56 (d, J = 6.9 Hz, 2H), 5.54 (t, J = 6.9 Hz, 1H), 5.54 (m, 1H), 6.44 (m, 1H), 6.97 (d, J = 8.7 Hz, 2H), 7.10 (s, 1H), 7.13 (s, 1H), 7.28 (d, J = 8.7 Hz, 2H), 7.45 (m, 1H) 8.10 (m, IH); IR (KBr) 3334, 1612, 1519, 1488, 1231, 1006, 833 cm &^lt; -1 ^&gt;. Ib-288 mp 89-90 ° C; Δ NMR (CDCl 3) δ 1.74 (s, 3H), 1.78 (s, 3H), 2.22 (s, 3H), 2.26 (s, 3H), 3.71 (d, J = 6.9 Hz, 2H), 5.32-5.36 ( m, 1H), 5.38 (s, 2H), 6.36-6.49 (m, 4H), 6.84 (dd, J = 0.6, 8.4 Hz, 1H), 7.06 (t, J = 8.1 Hz, 1H), 7.11 (s) (1H), 7.13 (s, 1H), 7.46-7.48 (m, 1H), 7.61 (dd, J = 2.4, 8.4Hz, 1H), 8.18 (dd, J = 0.9, 2.4Hz, 1H) IR (KBr) ): 3423, 2963, 2926, 2860, 1627, 1604, 1523, 1480, 1448, 1393, 1378, 1343, 1282, 1269, 1240, 1169, 1150, 1117, 1014, 1000 cm ¹ Ib-289 b. m.p. oil, ° C; @ 1 H NMR (CDCl3) .delta. 1.74 (s, 3H), 1.77 (s, 3H), 1.90 (t, J = 2.1 Hz, 3H), 2.22 (s, 3H), 3.71 (d, J = 6.9Hz, 2H), 4.99-5.01 (m, 2H), 5.33-5.37 (m, 1H), 6.37-6.47 (m, 2H), 6.86 (d, J = 8.4Hz, 1 H), 7.03-7.13 (m, 3H), 7.61 (dd, J = 2.4, 8.4Hz, 1 H), 8.17 (d, J = 2.1Hz, 1H) Ib-290 mp 104-105 ° C; @ 1 H NMR (CDCl3) .delta. 1.74 (s, 3H), 1.78 (s, 3H), 2.24 (s, 3H), 2.29 (s, 3H), 3.72 (d, J = 6.9 Hz, 2H), 5.33-5.36 (m, 1H), 6.37-6.78 (m, 4H), 7.06 (t, J = 8.4 Hz, 1H), 7.14 (s, 1H), 7.16 (s, 1H), 7.38 (d, J = 8.4 Hz, 1 H), 7.56 (t, J = 2.4 Hz, 1H), 7.77 (dd, J = 2.1, 8.1 Hz, 1H), 8.45 (dd, J = 0.6, 2.4 Hz, 1H) IR (KBr): 3396, 2976 , 2929, 2855, 1626, 1596, 1573, 1523, 1482, 1378, 1367, 1335, 1130, 1065 cm ^-1 Ib-291 mp 119-120 ° C; Δ NMR (CDCl 3) δ 1.73 (s, 3H), 1.77 (s, 3H), 2.01-2.06 (m, 4H), 2.21 (s, 3H), 2.29 (s, 3H), 3.49-3.54 (m, 4H) 3.71 (d, J = 6.6 Hz, 2H), 5.33-5.36 (m, 1 H), 6.35-6.46 (m, 3 H), 7.06 (t, J = 8.4 Hz, 1 H), 7.10 (s, 2H) 7.48 (dd, J = 2.7, 9.0 Hz, 1H), 8.20 (d, J = 2.1 Hz, 1H) IR (KBr): 3438, 2957, 2914, 2855, 1628, 1602, 1540, 1525, 1490, 1457 , 1416, 1341, 1306, 1235, 1168, 1115 cm ^1st Ib-292 oil, Ή NMR (CDCl 3) δ 1.78 (s, 3H), 1.82 (s, 3H), 2.27 (s, 3H), 2.30 (s, 3H), 4.56 (d, J = 6.9 Hz, 2H), 5.55 ( tm, J = 6.9 Hz, 1H), 7.99 (d, J = 8.7 Hz, 2H), 7.13 (s, 1H), 7.17 (s, 1H), 7.29 (d, J = 8.7 Hz, 2H), 7.37 ( m, 1H); 7.45 (m, H); 8.56-8.70 (m, 2H); IR (CHCl) 1672, 1607, 1514, 1494, 1471, 1450, 1383, 1234, 1230, 1174, 998, 978 cm ^first Ib-293 mp 114-115 ° C; Δ NMR (CDCl 3) δ 1.73 (s, 3H), 1.77 (s, 3H), 2.26 (s, 3H), 2.31 (s, 3H), 3.74 (d, J = 6.9 Hz, 2H), 3.99 (s, 3H), 5.35-5.44 (m, 1 H), 6.656.70 (m, 2 H), 6.81 (d, J = 8.4 Hz, 1 H), 7.10 (s, 1 H), 7.16 (s, 1 H), 7.17-7.22 (m, 2H), 7.60 (dd, J = 2.4, 8.4 Hz, 1H), 8.18 (d, J = 2.1 Hz, 1H) IR (KBr): 3333, 3006, 2968, 1612, 1524, 1483, 1387, 1367, 1319, 1300, 1288, 1240, 1024 cm · ¹ Ib-294 mp 75-76 ° C; @ 1 H NMR (CDCl3) .delta. 1.73 (s, 3H), 1.77 (s, 3H), 2.28 (s, 3H), 2.31 (s, 3H), 3.76 (d, J = 6.9 Hz, 2H), 4.17 (s) (2H), 5.39 (m, 1H), 6.75 (d, J = 8.4 Hz, 2H), 7.10-7.22 (m, 4H), 8.29 (d, J = 2.4 Hz, 1H), 8.42 (d, J = 2.4Hz, 1 H); IR (CHCl): 3426, 2923, 2868, 1613, 1557, 1530, 1499, 1478, 1427, 1381, 1353, 1301, 1245, 1093, 1007, 956, 929, 894 cm ¹

···· _ »

212

Table 118

Ib-295 mp 88-89 ° C Ή NMR (CDCl 3) δ 1.77 (s, 3H), 1.82 (s, 3H), 2.28 (s, 6H), 4.64 (d, J = 6.9 Hz, 2H), 5.44 (s, 2H) 5.53-5.58 (m, 1 H), 6.89 (dd, J = 0.6, 8.7 Hz, 1 H), 7.00-7.14 (m, 5H), 7.32-7.44 (m, 3 H), 7.49-7.53 (m, 2H) 7.62 (dd, J = 2.7, 8.7 Hz, 1H); 8.19 (dd, J = 0.6, 2.7 Hz, 1H); IR (nujol): 1602, 1285, 1129, 988, 836 cm &^lt; -1 ^&gt;. Ib-296 mp 110 ° C Ή NMR (CDCl 3) δ 1.77 (s, 3H), 1.81 (s, 3H), 2.27 (s, 6H), 2.28 (s, 3H), 4.01 (s, 3H), 4.64 (d, J) = 6.9Hz, 2H), 5.53-5.58 (m, IH), 6.82 (d, J = 8.4Hz, IH), 7.00-7.26 (m, 5H), 7.60 (dd, J = 2.4, 8.4Hz, IH) 8.18 (d, J = 2.4Hz, 1H); IR (nujol): 1598, 1283, 1273, 1124, 992, 838 cm &lt; -1 &gt;. Ib-297 mp 201-204 ° C; Δ NMR (CDCl 3) δ 1.80 (s, 3H), 1.83 (s, 3H), 1.97 (s, 6H), 1.98 (s, 6H), 4.88 (d, J = 6.9 Hz, 2H), 5.56-5.61 ( m, 1H), 6.75-6.80 (m, 2H), 6.83 (d, J = 8.1 Hz, 1H), 6.92-6.98 (ra, 2H), 7.41 (dd, J = 2.4, 8.7 Hz, 1H), 7.98 (d, J = 2.4 Hz, 1H) IR (KBr): 3452, 3368, 2927, 1619, 1599, 1517, 1487, 1465, 1378, 1350, 1275, 1240, 1125, 980 cm ^-1 Ib-298 mp 158-160 ° C; 1 H NMR (CDCl 3) δ 1.74 (s, 3H), 1.78 (s, 3H), 1.79 (s, 3H), 1.83 (s, 3H), 1.97 (s, 6H), 2.00 (s, 6H), 3.74 (d, J = 6.9 Hz, 2H), 4.88 (d, J = 6.9 Hz, 2H), 5.37-5.42 (m, 1H), 5.56-5.62 (m, 1H), 6.67-6.72 (m, 2H), 6.84 (d, J = 8.4Hz, 1 H), 6.94-7.00 (m, 2H), 7.41 (dd, J = 2.4, 8.7Hz, 1 H), 7.99 (dd, J = 0.6, 2.4Hz, 1 H) IR ( KBr): 3388, 2928, 2854, 1613, 1600, 1518, 1486, 1465, 1376, 1349, 1312, 1291, 1275, 1240, 1125, 983 cm @ ¹ Ib-299 mp 124-125 ° C; Ή NMR (CDCl 3) δ 1.25 (s, 3H), 1.27 (s, 3H), 1.80 (s, 3H), 1.83 (s, 3H), 1.97 (s, 6H), 2.00 (s, 6H), 3.62- 3.75 (m, 1H); 4.88 (d, J = 6.9Hz, 2H); 5.56-5.62 (m, 1H); 6.64-6.68 (m, 2H); 6.83 (d, J = 8.4Hz, 1H); 6.936 .98 (m, 2H), 7.41 (dd, J = 2.4, 8.4 Hz, 2H), 7.99 (d, J = 1.8 Hz, 1H) IR (KBr): 3391, 2965, 2930, 1613, 1600, 1519, 1412, 1376, 1362, 1349, 1316, 1277, 1242, 1181, 1125, 977 cm ¹ Ib-300 mp 116-119 ° C; Ή NMR (CDCl 3) δ 1.78 (s, 3H); 1.82 (s. 3H); 1.97 (s, 12H); 4.01 (s. 3H); 4.64 (d, J = 6.6 Hz, 2H); 5.58 (m, IH); 6.82-6. 87 (m, 2H); 6.91 (ddd, J = 1.8, 4.8, 11.7 Hz, 1H); 7.05 (dt, J = 1.5, 8.7 Hz, 1H); 7.41 (ddd, J = 1.5, 2.4, 8.7 Hz, 1H); 7.99 (d, J = 2.4 Hz, 1H); IR (KBr): 3432, 2944, 1603, 1514, 1496, 1462, 1297, 1281, 1263, 1245, 1210, 1113 cm &^lt; -1 ^&gt;. Ib-301 mp 150-153 ° C; Ή NMR (CDCl 3) δ 1.75 (s, 3H); 1.780 (s. 3H); 1,784 (s. 3H); 1.82 (s. 3H); 1.96 (s. 6H); 2.01 (s. 6H); 3.91 (t, J = 6.0 Hz, 2H); 4.50 (br t, J = 4.5 Hz, 1H); 4.64 (d, J = 6.9 Hz, 2H); 5.38 (m, IH); 5.57 (m, IH); 6.49 (m, IH); 6.84 (m, IH); 6.91 (ddd, J = 2.1, 3.3, 12 Hz, 1H); 7.04 (dt, J = 2.1, 8.4 Hz, 1H); 7.27 (m, IH); 7.91 (m, IH); IR (KBr): 3235, 2917, 1608, 1540, 1513, 1381, 1294, 1261 cm &^lt; -1 ^&gt;. Ib-302 mp 155-157 ° C; @ 1 H NMR (CDCl3) .delta. 1.30 (d, J = 6.3 Hz, 6H); 1.78 (s. 3H); 1.83 (s. 3H); 1.96 (s. 6H); 2.01 (s. 6H); 3.92 (sept, J = 6.3 Hz, 1 H); 4.54 (br. 1H); 4.64 (d, J = 6.6 Hz, 2H); 5.58 (m, IH); 6.48 (d, J = 7.5 Hz, 1H); 6.83-7.07 (m. 3H); 7.27 (m, IH); 7.89 (m. 1H); IR (KBr): 3419, 3249, 2969, 1610, 1537, 1513, 1463, 1389, 1293, 1263, 1241, 1209, 1180, 1113 cm &^lt; -1 ^&gt;. Ib-303 mp 134-137 ° C; Ή NMR (CDCl 3) δ 0.99-1.92 (m, 11H); 1.77 (s. 3H); 1.82 (s. 3H); 1.96 (s. 6H); 2.01 (s. 6H); 3.16 (t, J = 6.0 Hz, 2H); 4.64 (d, J = 6.6 Hz, 2H); 4.73 (brs, 1H); 5.57 (m, IH); 6.49 (m, IH); 6.82-6.94 (m, 2H); 7.04 (dt, J = 1.5, 7.8 Hz, 1H); 7.27 (m, IH); 7.88 (m. 1H); IR (KBr): 3425, 3250, 2925, 2852, 1607, 1533, 1512, 1448, 1294, 1261, 1240, 1211, 1115 cm &^lt; -1 ^&gt;.

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213

Table 119

Ib-304 mp 154-156 ° C; Ή NMR (CDCl 3) δ 1.77 (s, 3H); 1.82 (s. 3H); 1.98 (s. 6H); 2.00 (s. 6H); 4.63 (d, J = 5.7 Hz, 2H); 5.00 (br. 1H); 5.57 (m, IH); 6.52 (dd, J = 2.4, 8.4 Hz, 1H); 6.85-7.01 (m, 2 H); 7.04 (dt, J = 1.8, 8.4 Hz, 1H); 7.26-7.33 (m. 2H); 7.77 (m, IH); 7.994 (m, IH); 8.56 (m, IH); 8.69 (br. S, 1H); IR (KBr): 3256, 2917, 1603, 1514, 1463, 1427, 1381, 1296, 1263, 1239, 1210, 1112, 1004 cm &^lt; -1 ^&gt;. Ib-305 m.p. 127-129 [deg.] C .; Ή NMR (CDCl 3) δ 0.99 (d, J = 6.6 Hz, 6H); 1.50-1.80 (m, 3 H); 1.77 (s. 3H); 1.82 (s. 3H); 1.96 (s. 6H); 2.01 (s. 6H); 3.29-3.36 (m. 2H); 4.53 (br. T, 1H); 4.64 (d, J = 6.6 Hz, 2H); 5.57 (m, IH); 6.49 (d, J = 8.4 Hz, 1H); 6.81-6.94 (m. 2H); 7.04 (dt, J = 1.5, 8.4 Hz, 1H); 7.28 (m. 2H); 7.90 (m, IH); IR (KBr): 3442, 3259, 2956, 1609, 1542, 1512, 1457, 1383, 1293, 1260, 1238, 1205, 1114 cm &lt; -1 &gt;. Ib-306 mp 86-89 ° C; @ 1 H NMR (CDCl3) .delta.1.04 (d, J = 6.6 Hz, 5H); 1.77 (s. 3H); 1.82 (s. 3H); 1.86-1.95 (m. 1H); 196 (s. 6H); 2.01 (s. 6H); 3.14 (t, J = 6.3 Hz, 2H); 4.64 (d, J = 6.9 Hz, 2H); 4.67 (br t, IH); 5.57 (m, IH); 6.49 (m, IH); 6.82-7.07 (m. 3H); 7.28 (dt, J = 1.8, 8.4 Hz, 1H); 7.89 (m. 1H); IR (KBr): 3343, 2957, 1610, 1513, 1465, 1382, 1294, 1263, 1240, 1114 cm &^lt; -1 ^&gt;. Ib-307 mp 157-159 ° C; ¹ H NMR (CDCl 3) δ 1.77 (s, 3H); 1.82 (s. 3H); 1.96 (s. 6H); 2.00 (s. 6H); 4.64 (d, J = 6.6 Hz, 2H); 4.77 (d, J = 5.4 Hz, 2H); 4.94 (br. 1H). 5.57 (m, IH); 6.56 (m, IH); 6.81-7.09 (m. 5H); 7.24-7.30 (m, 2 H); 7.96 (d, J = 2.4 Hz, 1H); IR (KBr): 3393, 2925, 1610, 1512, 1295, 1263, 1240 cm &^lt; -1 ^&gt;. Ib-308 mp 175-177 ° C; Ή NMR (CDCl 3) δ 1.77 (s, 3H); 1.82 (s. 3H); 1.96 (s. 6H); 2.00 (s. 6H); 4.58 (d, J = 6.0 Hz, 2H); 4.64 (d, J = 6.9 Hz, 2H); 4.98 (br. S, 1H); 5.57 (m, IH); 6.54 (m, IH); 6.81-6.94 (m. 2H); 7.04 (dt, J = 1.8, 8.4 Hz, 1H); 7.14 (dd, J = 1.8, 5.1 Hz, 1H); 7.27 (m, IH); 7.35 (dd, J = 3.0, 4.8 Hz, 1 H); 7.94 (m, IH); IR (KBr): 3233, 2912, 1546, 1512, 1453, 1420, 1384, 1317, 1294, 1259, 1238, 1204, 1116 cm &^lt; -1 ^&gt;. Ib-309 mp 134-137 ° C; Ή NMR (CDCl 3) δ 1.77 (s, 3H); 1.82 (s. 3H); 1.98 (s. 6H); 2.00 (s. 6H); 4.58 (d, J = 5.4 Hz, 2H); 4.64 (d, J = 6.6 Hz, 2H); 4.88 (br t, IH); 5.57 (m, IH); 6.30 (dd, J = 0.9, 3.0 Hz, 1H); 6.36 (dd, J = 4.2, 6.3 Hz, 1H); 6.57 (m, IH); 6.86 (m, IH); 6.91 (ddd, J = 2.1, 3.6, 11.7 Hz, 1H); 7.03 (dt, J = 1.8, 8.4 Hz, 1H); 7.28 (m, IH); 7.40 (m, IH); 7.94 (m, IH); IR (KBr): 3379, 2928, 1513, 1294, 1263, 1240 cm &^lt; -1 ^&gt;. Ib-310 mp 124-126 ° C; Ή NMR (CDCl 3) δ 1.77 (s, 3H); 1.82 (s. 3H); 1.97 (s. 6H); 2.00 (s. 6H); 4.41 (d, J = 5.4 Hz, 2H); 4.64 (d, J = 6.3 Hz, 2H); 4.73 (br t, IH); 5.57 (m, IH); 6.47 (m, 1H); 6.54 (m, 1H); 6.82-7.08 (m, 3H); 7.27 (m, 1H); 7.43 (t, J = 1.8 Hz, 1H); 7.46 (m, 1H); 7.94 (d, J = 2.4 Hz, 1H); IR (KBr): 3456, 3236, 2254, 1605, 1512, 1468, 1382, 1293, 1261, 1240, 1209, 1114 cm &^lt; -1 ^&gt;. Ib-311 mp 143-145 ° C; Ή NMR (CDCl 3) δ 1.78 (s, 3H); 1.82 (s. 3H); 1.97 (s. 6H); 2.00 (s. 6H); 4.64 (d, J = 7.0 Hz, 2H); 4.74 (d, J = 5.2 Hz, 2H); 5.58 (m, IH); 5.76 (m, 1H); 6.61 (d, J = 8.4Hz, 1H); 6.82-7.29 (m. 4H); 7.40 (d, J = 8.0 Hz, 1H); 7.70 (m, IH); 7.95 (d, J = 2.0 Hz, 1H); 8.61 (d, J = 4.8 Hz, 1H); IR (KBr): 3251, 2929, 1608, 1514, 1440, 1380, 1295, 1264, 1252, 1240, 1207 cm &^lt; -1 ^&gt;. Ib-312 mp 166-167 ° C; Ή NMR (CDCl 3) δ 1.77 (s, 3H); 1.82 (s. 3H); 1.96 (s. 6H); 1.99 (s. 6H); 4.51 (br. S, 2H); 4.64 (d, J = 6.6 Hz, 2H); 5.57 (m, IH); 6.62 (m. 1H); 6.84 (m, IH); 6.90 (m, IH); 7.04 (m, IH); 7.27 (m, IH); 7.90 (m, IH); IR (KBr): 3467, 3304, 3168, 2917, 1638, 1619, 1516, 1388, 1297, 1265, 1240, 1209 cm &^lt; -1 ^&gt;.

* *

214 ····· · 4 · · · · · · · · · · · · ·

Table 120

Ib-313 amorphous; Δ NMR (CDCl 3) δ 1.75 (s, 3H), 1.78 (s, 3H), 1.98 (s, 6H), 2.01 (s, 6H), 3.69 (s, 1H), 3.91 (t, J = 5.6 Hz) 2H, 4.64 (br s, 1H), 5.38 (t, J = 6.9Hz, 1H), 6.50 (d, J = 8.7Hz, 1H), 6.75-6.79 (m, 2H), 6.92-6.97 (m) (2H), 7.30 (dd, J = 8.7, 2.1 Hz, 1 H), 7.91 (d, J = 2.1 Hz, 1 H), 7.56 (dd, J = 9.3, 2.4 Hz, 1 H); IR (KBr): 3447, 3414, 3364, 1605, 1518, 1464, 1377, 1278, 819 cm ^&lt; -1 ^&gt; Ib-314 mp 172-173 ° C; @ 1 H NMR (CDCl3) .delta. 1.75 (s, 6H), 1.78 (s, 3H), 1.78 (s, 3H), 2.00 (s, 6H), 2.01 (s, 6H), 3.4 (br s, 1H), 3.74 (d, J = 6.6Hz, 2H), 3.91 (t, J = 6.0Hz, 2H), 4.53 (brs, 1H), 5.35-5.42 (m, 2H), 6.49 (dd, J = 8.4, 0.9) Hz, 1H), 6.67-6.71 (m, 2H), 6.94-7.00 (m, 2H), 7.29 (dd, J = 8.4, 2.4Hz, 1H), 7.93 (dd, J = 2.4, 0.9Hz, 1H) ; IR (KBr): 3415, 3229, 1606, 1521, 1465, 1379, 1315, 1141, 985, 815 cm ^&lt; -1 ^&gt; Ib-315 mp 207-209 ° C; Ή NMR (CDCl 3) δ 1.76 (s, 3H), 1.76 (s, 3H), 1.96 (s, 6H), 1.98 (s, 6H), 3.4 (br s, 1H), 3.88 (d, J = 7.8Hz) (2H), 5.42 (t, J = 7.8Hz, 1H), 6.76-6.82 (m, 2H), 6.92-6.98 (m, 2H), 7.26 (d, J = 7.8Hz, 1H), 7.34 (dd, J = 7.8, 2.1 Hz, 1 H), 8.29 (d, J = 2.1 Hz, 1 H); IR (KBr): 3452, 3367, 1619, 1517, 1457, 1353, 1280, 1176, 1107, 820, 540 cm &lt; -1 &gt; Ib-316 b. 1.156-158 ° C; Ή NMR (CDCl 3) δ 1.75 (s, 3H), 1.76 (s, 3H), 1.76 (s, 3H), 1.78 (s, 3H), 1.97 (s, 6H), 2.00 (s, 6H), 3.75 ( d, J = 6.6Hz, 2H), 3.88 (d, J = 7.7Hz, 2H), 5.40 (t, J = 6.6Hz, 2H), 5.42 (t, J = 7.7Hz, 1H), 6.68-6.73 ( m, 2H), 6.93-7.00 (m, 2H), 7.26 (dd, J = 8.1, 1.1Hz, 1H), 7.34 (dd, J = 8.1,1.1Hz, 1H), 8.29 (dd, J = 2.1, 1.1 Hz, 1 H); IR (KBr): 3391, 1612, 1518, 1462, 1180, 1108, 820, 807, 546 cm &lt; -1 &gt;. Ib-317 b. 1.161-164 ° C; Δ NMR (CDCl 3) δ 1.77 (s, 3H), 1.77 (s, 3H), 1.99 (s, 6H), 1.99 (s, 6H), 2.11 (s, 6H), 3.89 (d, J = 7.8Hz, 2H), 5.43 (t, J = 7.8Hz, 1H), 5.94 (s, 2H), 7.21-7.39 (m, 6H), 8.31 (dd, J = 2.3, 0.8Hz, 1H); IR (KBr): 3439, 1586, 1520, 1449, 1406, 1110, 999, 824, 750, 565 cm ^&lt; -1 ^&gt; Ib-318 b. 1.137-138 ° C, ¹ H NMR (CDCl 3) δ 1.75 (s, 3H), 1.78 (s, 6H), 1.81 (s, 3H), 1.82 (s, 3H), 1.89 (s, 6H), 1.98 (s, 6H), 2.15 (s, 3H), 3.75 (d, J = 6.9Hz, 2H), 4.86 (d, J = 7.2Hz, 2H), 5.40 (m, 1H), 5.59 (m, 1H) 6.64-6.71 (m, 3H), 6.94-6.99 (m, 2H), 7.26 (d, J = 8.4Hz, 1H). IR (KBr): 3412, 2914, 1611, 1592, 1460, 1311, 1297, 1282, 1237 cm &lt; ^{4 &gt;} Ib-319 b. 1.129-130 ° C, Ή NMR (CDCl 3) δ 1.74 (s, 3H), 1.79 (s, 6H), 1.82 (s, 3H), 1.98 (s, 6H), 1.99 (s, 6H), 2.25 (s, 3H), 3.75 (d, J = 6.9Hz, 2H), 4.90 (d, J = 6.6Hz, 2H), 5.40 (br t, J = 6.9Hz, 1H), 5.59 (br t, J = 6.9 Hz (1H), 6.70 (m, 2H), 6.97 (m, 2H), 7.23 (d, J = 2.1Hz, 1H), 7.82 (d, J = 2.1Hz, 1H) Ib-320 mp 153-154 ° C, 1 H NMR (CDCl 3) δ 1.75 (s, 3H), 1.79 (s, 6H), 1.83 (s, 3H), 1.89 (s, 6H), 1.96 (s, 3H), 1.99 (s, 6H), 2.15 (s, 3H), 3.75 (d, J = 6.9Hz, 2H), 4.86 (d, J = 6.9Hz, 2H), 5.40 (m, 1H), 5.58 (m, 1H) 6.69-6.73 (m, 3H); 6.94-7.01 (m, 2H); 7.84 (s, 1 H). IR (KBr): 3386, 2928, 1608, 1518, 1464, 1377, 1315, 1180, 1122, 1028 cm @ -1. Ib-321 b. 1.115-117 ° C; Δ NMR (CDCl 3) δ 1.60 (s, 3H), 1.73 (s, 3H), 1.75 (s, 3H), 1.78 (s, 3H), 1.95 (s, 6H), 2.01 (s, 6H), 3.60 ( d, J = 7.7Hz, 2H), 3.91 (t, J = 6.0Hz, 2H), 4.52 (m, 1H), 5.32-5.42 (m, 2H), 6.49 (d, J = 8.4Hz, 1H), 7.057.11 (m, 2H); 7.28 (dd, J = 8.4, 2.3 Hz, 1H); 7.39-7.44 (m, 2H); 7.91 (d, J = 2.3 Hz, 1H); IR (KBr): 3425, 1609, 1541, 1391, 1378, 814, 550 cm @ -1.

• 4

4 4 4 · · 0 · 000 · 000 · · · · ·

0 00

000

0 0 ·

0 0 ·

0 0 ·

0 0 ·

0 0 0

215

Table 121

Ib-322 m.p. 119-122 [deg.] C .; Δ NMR (CDCl 3) δ 1.75 (s, 3H), 1.77 (s, 3H), 1.78 (s, 3H), 1.82 (s, 3H), 2.01 (s, 6H), 2.03 (s, 3H), 3.34 ( s, 3H), 3.91 (dd, J = 5.9, 5.9 Hz, 2H), 4.51 (t, J = 5.2 Hz, 1H), 4.64 (d, J = 6.7 Hz, 2H), 5.38 (m, 1H), 5.57 (m, 1H); 6.47 (d, J = 8.5Hz, 1H); 6.97-7.08 (m, 3H); 7.23-7.28 (m, 1H); 7.72 (d, J = 1.8Hz, 1H); IR (nujor): 3325, 1926, 2853, 1608, 1538, 1514, 1457, 1389, 1296, 1262, 1214, 1110, 1006 cm &lt; -1 &gt; Ib-323 Ή NMR (300 MHz, CDCl 3) δ 1.80 (d, J = 0.9Hz, 3H), 1.83 (d, J = 0.9Hz, 3H), 1.98 (s, 6H), 2.06 (s, 3H), 3.32 (s) 3.88 (d, J = 6.9 Hz, 2H), 5.555.62 (m, 1 H), 6.80 (d, J = 7.8 Hz, 2 H), 6.85 (dd, J = 8.6, 0.8 Hz, 1 H) 7.11 (d, J = 7.8 Hz, 2H), 7.40 (dd, J = 8.6, 2.6 Hz, 1 H), 7.98 (dd, J = 2.6, 0.8 Hz, 1 H) Ib-324 Δ NMR (300 MHz, CDCl 3) δ 1.74 (s, 3H), 1.78 (s, 3H), 1.80 (s, 3H), 1.83 (s, 3H), 1.98 (s, 3H), 2.07 (s, 3H) 3.33 (s, 3H), 3.75 (d, J = 6.6Hz, 2H), 4.88 (d, J = 6.9 Hz, 2H), 5.36-5.43 (m, 1 H), 5.55-5.62 (m, 1 H), 6.71 (d, J = 8.0 Hz, 2 H), 6.84 (dd, J = 2.4, 0.8 Hz, 1 H) 7.40 (dd, J = 8.0 Hz, 2H), 7.40 (dd, J = 8.6, 2.4 Hz, 1H), 7.98 (dd, J = 2.4, 0.8 Hz, 1H) Ib-325 Δ NMR (300 MHz, CDCl 3) δ 1.80 (s, 3H), 1.83 (s, 3H), 1.97 (s, 6H), 2.06 (s, 3H), 3.32 (s, 3H), 3.92 (s, 3H) 4.46 (s, 2H), 4.88 (d, J = 6.9Hz, 2H), 5.555.62 (m, 1H), 6.71 (d, J = 8.0Hz, 2H), 6.84 (d, J = 8.4Hz, 1H), 7.12 (d, J = 8.0Hz, 2H), 7.40H, dd, J = 8.4, 2.2Hz, 1H), 7.50 (d, J = 8.1Hz, 2H), 7.98 (d, J = 2.2Hz) (1H), 8.04 (d, J = 8.1 Hz, 2H) Ib-326 Δ NMR (300 MHz, CDCl 3) δ 1.80 (s, 3H), 1.83 (s 3H), 1.97 (s, 6H), 2.06 (s, 3H), 3.32 (s, 3H), 4.48 (s, 2H), 4.88 (d, J = 6.9Hz, 2H), 5.55-5.61 (m, IH), 6.70 (d, J = 7.8Hz, 2H), 6.85 (d, J = 8.4Hz, IH), 7.12 (d, J) = 7.8 Hz, 2H), 7.40 (dd, J = 8.4, 0.7 Hz, 1 H), 7.53 (d, J = 8.1 Hz, 2 H), 7.99 (d, J = 0.7 Hz, 1 H), 8.11 (d, J) = 8.1Hz, 2H) Ib-327 Δ NMR (300 MHz, CDCl 3) δ 1.80 (s, 3H), 1.83 (s, 3H), 1.98 (s, 3H), 2.07 (s, 3H), 3.32 (s, 3H), 3.86 (s, 3H) 3.87 (s, 6H), 4.33 (s, 2H), 4.88 (s, J = 6.6Hz, 2H), 5.55-5.60 (m, 1H), 6.67 (s, 2H), 6.76 (d, J = 7.1) Hz, 2H), 6.85 (dd, J = 8.4, 0.6 Hz, 1 H), 7.15 (d, J = 7.1 Hz, 2 H), 7.40 (dd, J = 8.4, 2.4 Hz, 1 H), 7.98 (dd, J) = 2.4, 0.6Hz, 1H) Ib-328 Δ NMR (300 MHz, CDCl 3) δ 1.80 (s, 3H), 1.83 (s, 3H), 1.97 (s, 6H), 2.06 (s, 3H), 3.31 (s, 3H), 4.38 (s, 2H) 4.88 (d, J = 7.2Hz, 2H), 5.55-5.62 (m, 1H), 6.29 (d, J = 3.0Hz, 1H), 6.35 (dd, J = 3.0Hz, 1.8Hz, 1H), 6.77 ( d, J = 8.1 Hz, 2H), 6.84 (dd, J = 8.2, 0.6 Hz, 1H), 7.14 (d, J = 8.1 Hz, 2H), 7.399 (dd, J = 1.8, 0.8 Hz, 1H), 7.40 (dd, J = 8.2, 2.4Hz, 1 H), 7.98 (dd, J = 2.4, 0.6Hz, 1 H) Ib-329 m.p. 110-111 [deg.] C .; Δ NMR (CDCl 3) δ 1.80 (s, 3H), 1.83 (s, 3H), 1.98 (s, 6H), 2.06 (s, 3H), 3.33 (s, 3H), 4.88 (d, J = 6.9Hz, 2H), 5.59 (m, 1H), 6.79 (d, J = 8.7Hz, 2H), 6.84 (dd, J = 8.4 and J = 0.9Hz, 1H), 6.95 (d, J = 7.2Hz, 2H), 7.56 (dd, J = 8.4 and 2.7 Hz, 1H); 8.11 (dd, J = 2.4 and 0.6 Hz, 1H); IR (CHCl3): 3462, 3016, 2934, 1620, 1604, 1279, 1241, 1087, 982, cm @ -1. Ib-330 m.p. 115-116 [deg.] C .; Ή NMR (CDCl 3) δ 1.74 (s, 3H), 1.78 (s, 3H), 1.80 (s, 3H), 1.83 (s, 3H), 2.00 (s, 6H), 2.06 (s, 3H), 3.33 (s, 3H), 3.75 (d, J = 6.6Hz, 2H), 4.88 (d, J = 6.9Hz, 2H) 5.39 (m, 1H); 5.59 (m, 1H); 6.71 (d, J = 7.8Hz, 2H); 6.84 (dd, J = 8.4 and 0.6Hz, 1H), 6.97 (d, J = 7.5Hz, 2H), 7.56 (dd, J = 8.4 and 2.4Hz, 1H), 8.11 (dd, J = 2.4 and 0.9Hz) (1H); IR (CHCl 3): 3424, 3004, 2975, 2934, 2860, 1612, 1491, 1402, 1377, 1280, 1241, cm -1.

φ φ φ φ φ φ φ φ φ φ φ

2Ϊ6

φ

Φ Φ

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Φ Φ Φ ·

Φ Φ «Φ

Table 122

Ib-331 m.p. Mp 111-112 ° C; @ 1 H NMR (CDCl3) .delta. 1.26 (s, 3H), 1.28 (s, 3H), 1.79 (s, 3H), 1.83 (s, 3H), 2.00 (s, 6H), 2.06 (s, 3H), 3.33 (s, 3H), 3.68 (m, 1H), 4.88 (d, J = 6.9Hz, 2H), 5.59 (m, 1H), 6.67 (d, J = 8.4Hz, 2H), 6.84 (dd, J = 8.4 and 6.0 Hz, 1H), 6.95 (d, J = 7.2Hz, 2H), 7.56 (dd, J = 8.4 and 2.4Hz, 1H), 8.12 (dd, J = 2.4 and 0.6 Hz, 1 H); IR (CHCl3): 3423, 3018, 2975, 2934, 2872, 1612, 1354, 1317, 1377, 1280, 1242, cm @ -1. Ib-332 mp 139-140 ° C; 1 H NMR (CDCl 3) δ 1.14-1.46 (m 5H), 1.65-1.80 (m 3H), 1.82 (s, 3H), 1.83 (s, 3H), 2.00 (s, 6H), 2.06 (s, 3H) 3.33 (s, 3H), 2.10-2.15 (m, 2 H), 3.30 (m, 1 H), 4.88 (d, J = 7.2 Hz, 2 H), 5.59 (m, 1 H), 6.87 (d, J = 8.7) Hz, 2H), 6.84 (dd, J = 8.7 and 0.9 Hz, 1H), 6.94 (d, J = 7.2 Hz, 2H), 7.56 (dd, J = 8.7 and 2.7 ohms), 8.11 (dd, J) = 2.7 and 0.9 Hz, 1H); IR (CHCl 3): 3422, 3002, 2933, 2856, 1612, 1354, 1318, 1280, 1242, 1130, 1087, cm -1. Ib-333 m.p. 155-156 [deg.] C .; Δ NMR (CDCl 3) δ 1.80 (s, 3H), 1.83 (s, 3H), 1.99 (s, 6H), 2.06 (s, 3H), 3.33 (s, 3H), 4.38 (s, 2H), 4.89 ( d, J = 6.9Hz, 2H), 5.59 (m, 1H), 6.30 (m, 1H), 6.35-6.37 (m, 1H), 6.77 (d, J = 8.4Hz, 2H), 6.83 (dd, J) = 8.4 and 0.9 Hz, 1H), 6.98 (d, J = 7.5 Hz, 2H), 7.40 (dd, J = 2.1 and 0.9 Hz, 1H) 7.57 (dd, J = 8.7 and 2.7 Ηζ, ΙΗ) 8.12 (dd J = 2.4 and 0.6 Hz (1H); IR (CHCl3): 3424, 2934, 2861, 1613, 1280, 1241, 1217, cm &lt; -1 &gt; Ib-334 mp 142-145 ° C; Δ NMR (CDCl 3) δ 1.99 (s, 3H), 2.06 (s, 3H), 3.33 (s, 3H), 3.79 (brs, 2H), 5.40 (s, 2H), 6.40 (dd, J = 2.0, 3.2) Hz, 1H), 6.49 (d, J = 3.3 Hz, 1H), 6.78 (d, J = 8.4 Hz, 2H), 6.87 (dd, J = 0.8, 8.3 Hz, 1H), 6.95 (brd, J = 7.2) Hz, 2H), 7.47 (dd, J = 0.9, 1.5Hz, 1H), 7.58 (dd, J = 2.6, 8.6Hz, 1H), 8.13 (dd, J = 0.8, 2.6Hz, 1H); IR (Nujor): 3342, 2924, 2854, 1611.1523, 1493, 1458, 1283, 1011, 824 cm ^-1 Ib-335 mp 158-159 ° C; Δ NMR (CDCl 3) δ 1.80 (s, 3H), 1.83 (s, 3H), 2.00 (s, 6H), 2.06 (s, 3H), 3.33 (s, 3H), 4.38 (s, 2H), 4.89 ( d, J = 7.0 Hz, 2H), 5.59 (m, 1H), 6.74 (d, J = 8.6 Hz, 2H), 6.84 (dd, J = 0.7, 8.4 Hz, 1H), 6.98 (brd, J = 6.9) Hz, 2H), 7.28-7.46 (m, 5H), 7.56 (dd, J = 2.5, 8.5Hz, 1 H), 8.12 (dd, J = 0.7, 2.3Hz, 1 H), IR (nujor): 3357, 2926 , 2854, 1613, 1526, 1491, 1452, 1279, 1090, 997, 823, 732 cm ' Ib-336 mp 116-117 ° C; Δ NMR (CDCl 3) δ 1.80 (s, 3H), 1.83 (s, 3H), 2.00 (s, 6H), 2.06 (s, 3H), 2.30 (s, 3H), 3.33 (s, 3H), 4.31 ( s, 2H), 4.88 (d, J = 6.9 Hz, 2H), 5.59 (m, 1H), 5.93 (m, 1H), 6.17 (d, J = 3.1 Hz, 1H), 6.76 (d, J = 8.6) Hz, 2H), 6.84 (d, J = 8.5 Hz, 1H), 6.98 (d, J = 6.7 Hz, 2H), 7.56 (dd, J = 2.3, 8.5 Hz, 1H), 8.12 (d, J = 2.3) Hz, 1H) IR (Nujor): 3349, 2925, 2854, 1611, 1525, 1490, 1455, 1280, 1240, 979, 822, 782 cm · ¹ Ib-337 mp 94-97 ° C; @ 1 H NMR (CDCl3) .delta. 1.66 (brd, J = 6.7 Hz, 3H), 1.73 (s, 3H), 1.80 (s, 3H), 1.83 (s, 3H), 1.99 (s, 6H), 2.06 (s) 3.88 (d, J = 6.9 Hz, 2H), 5.52-5.62 (m, 2H), 6.70 (d, J = 8.6 Hz, 2H), 3.33 (s, 3H), 3.69 (brs, 2H) 6.86 (dd, J = 0.7, 8.4Hz, 1 H), 6.95 (brd, J = 7.4Hz, 2 H), 7.56 (dd, J = 2.5, 8.5Hz, 1 H), 8.11 (dd, J = 0.7, 2.3) Hz, 1H), IR (KBr): 3409, 3325, 2927, 2857, 1612, 1523, 1457, 1279, 1085, 1002, 986, 820 cm ^&lt; -1 ^&gt; Ib-338 mp 161-163 ° C; Δ NMR (CDCl 3) δ 1.80 (s, 3H), 1.83 (s, 3H), 2.00 (s, 6H), 2.06 (s, 3H), 3.33 (s, 3H), 3.86 (s, 3H), 3.87 ( s, 6H), 4.42 (s, 2H), 4.88 (d, J = 7.0 Hz, 2H), 5.59 (m, 1H), 6.66 (s, 2H), 6.75 (d, J = 8.6 Hz, 2H), 6.84 (dd, J = 0.6, 8.5Hz, 1 H), 6.99 (brd, J = 6.7Hz, 2 H), 7.56 (dd, J = 2.4, 8.4Hz, 1 H), 8.12 (dd, J = 0.6, 2.3Hz) IR (KBr): 3373, 2934, 2831, 1604, 1592, 1522, 1457, 1280, 1240, 1124, 981, 822 cm ^&lt; -1 ^&gt;

217 ·· ···· ♦ · · ·

9 9 9 9 9 ·

9 · · · · · · · · · · · · · · · · ·

Table 123

Ib-339 mp 113-115 ° C; Δ NMR (CDCl 3) δ 1.74 (s, 3H), 1.78 (s, 3H), 1.80 (d, J = 0.9 Hz, 3H), 2.00 (s, 6H), 2.06 (s, 3H), 3.33 (s, 3.H), 3.75 (d, J = 6.7 Hz, 2H), 4.83 (dd, J = 5.3 Hz, 2H), 5.39 (m, 1H), 5.78-5.96 (m, 2H), 6.70 (d, J = 8.6) Hz, 2H), 6.87 (dd, J = 0.7, 8.5Hz, 1H), 6.97 (brd, J = 7.3Hz, 2H), 7.57 (dd, J = 2.4, 8.4Hz, 1H), 8.11 (dd, J) = 0.7, 2.5Hz, 1 H); IR (nujor): 3367, 2924, 2853, 1611, 1520, 1457, 1278, 1241, 992, 820 cm ^-1 Ib-340 mp 90-92 ° C; Δ NMR (CDCl 3) δ 1.75 (s, 3H), 178 (s, 3H), 2.00 (s, 6H), 2.06 (s, 3H), 2.59 (dt, J = 6.7, 6.7Hz), 3.33 (s, 3H), 3.75 (d, J = 6.9 Hz, 2H), 4.42 (t, J = 6.8 Hz, 2H), 5.12 (brd, J = 10.2 Hz, 1H), 5.20 (ddt, J = 1.6, 1.6, 17.2Hz, 1H), 5.39 (m, 1H), 5.96 (ddt, J = 6.7, 10.3, 17.1Hz, 1H), 6.70 (d, J = 8.6Hz, 2H), 6.83 (dd, J = 0.7, 8.4) Hz, 1H), 6.96 (brd, J = 6.9Hz, 2H), 7.57 (dd, J = 2.3, 8.5Hz, 1H), 8.11 (dd, J = 0.7, 2.4Hz, 1H); IR (nujor): 3362, 2952, 2925, 2854, 1611, 1604, 1519, 1466, 1280, 819 cm ^&lt; -1 ^&gt; Ib-341 mp 97-98 ° C; Δ NMR (CDCl 3) δ 1.04 (t, J = 7.5Hz, 3H), 1.75 (s, 3H), 1.78 (s, 3H), 2.00 (s, 6H), 2.06 (s, 3H), 2.22 (dq, J = 7.0, 7.1Hz, 2H); 3.33 (s, 3H); 3.75 (d, J = 6.9Hz, 2H); 4.95 (d, J = 5.3Hz, 2H); 5.39 (m, 1H); 5.71 ( dt, J = 6.1, 11.0Hz, 1 H, 5.75 (dt, J = 6.1, 10.8Hz, 1 H), 6.70 (d, J = 8.8Hz, 2 H), 6.84 (dd, J = 0.7, 8.5Hz, 1 H) 6.97 (brd, J = 6.9 Hz, 2H), 7.57 (dd, J = 2.4, 8.4 Hz, 1H), 8.12 (dd, J = 0.7, 2.5 Hz, 1H), IR (KBr): 3341, 2965 , 2930, 1612, 1523, 1491, 1456, 1281, 1243, 1089, 991, 822 Ib-342 mp 129-130 ° C; Δ NMR (CDCl 3) δ 1.74 (s, 3H), 1.78 (s, 3H), 1.92 (t, J = 2.1Hz, 3H), 2.00 (s, 6H), 2.05 (s, 3H), 3.32 (s) (3H), 3.75 (d, J = 6.6Hz, 2H), 5.02 (m, 2H), 5.40 (m, 1H), 6.72 (d, J = 8.4Hz, 2H), 6.89 (dd, J = 8.4 and 0.6 Hz, 1H), 6.97 (d, J = 7.2 Hz, 2H), 7.59 (dd, J = 8.4 and 2.4 Hz, 1H), 8.12 (dd, J = 2.4 and 0.6 Hz, 1H); IR (CHCl 3): 3424, 3004, 2933, 2858, 1612, 1346, 1279, 1241, cm ^-1 . Ib-343 mp 137-138 ° C; Δ NMR (CDCl 3) δ 1.75 (s, 3H), 1.78 (s, 3H), 2.00 (s, 6H), 2.06 (s, 3H), 3.33 (s, 3H), 3.75 (d, J = 6.9Hz, 2H), 5.40 (m, 3H), 6.40 (dd, J = 3.3 and 1.8 Hz, 1H), 6.49 (d, J = 3.3 Hz, 1H), 6.70 (d, J = 8.7 Hz, 2H), 6.87 ( dd, J = 9.0 and 0.6 Hz, 1 H, 6.97 (d, J = 7.5 Hz, 2 H), 7.47 (dd, J = 1.8 and 0.9 Hz, 1 H), 7.59 (dd, J = 8.4 and 2.4 Hz, 1 H) 8.13 (dd, J = 2.4 and 0.6 Hz, 1H); IR (CHCl 3): 3424, 3004, 2933, 2860, 1612, 1402, 1453, 1346, 1280, cm ^-1 . Ib-344 mp 144-146 ° C; Δ NMR (CDCl 3) δ 1.80 (s, 3H), 1.84 (s, 3H), 1.85 (t, J = 2.4 Hz, 3H), 2.00 (s, 6H), 2.07 (s, 3H), 3.34 (s, 3H), 3.89 (q, J = 2.4 Hz, 2H), 4.89 (d, J = 6.9 Hz, 2H), 5.60 (m, 1H), 6.76 (d, J = 8.4 Hz, 2H), 6.85 (d, J = 8.4 Hz, 1H), 7.00 (brd, J = 7.5 Hz, 2H), 7.57 (dd, J = 2.4, 8.4 Hz, 1H), 8.13 (d, J = 2.4 Hz, 1H); IR (CHC): 3451, 3395, 3024, 3015, 2934, 1621, 1604, 1518, 1491, 1280, 993, 825 cm ¹ Ib-345 mp 113-115 ° C; Δ NMR (CDCl 3) δ 1.75 (s, 3H), 1.77 (s, 3H), 2.00 (s, 6H), 2.05 (s, 3H), 3.32 (s, 3H), 3.75 (d, J = 6.7Hz, 2H), 4.64 (dd, J = 3.9, 29.2Hz, 1 H), 4.66 (dd, J = 2.9, 29.2Hz, 1 H), 4.81 (dd, J = 3.0, 47.5Hz, 1 H), 4.82 (dd, J 2) = 3.9, 47.4Hz, 1 H), 5.40 (m, 1 H), 6.70 (d, J = 8.6 Hz, 2 H), 6.90 (dd, J = 0.7, 8.4 Hz, 1 H), 6.96 (brd, J = 7.5 Hz) (2H), 7.59 (dd, J = 2.4, 8.4 Hz, 1H), 8.09 (dd, J = 0.7, 2.5 Hz, 1H); IR (nujor): 3399, 2925, 2854, 1612, 1519, 1491, 1450, 1283, 1087, 929 cm ^&lt; -1 ^&gt;

999 ·

9 9 9

9 9 · 9 9 9

99

Table 124

Ib-346 m.p. Mp 111-112 ° C; Δ NMR (CDCl 3) δ 1.75 (s, 3H), 1.78 (s, 3H), 2.00 (s, 6H), 2.05 (s, 3H), 3.32 (s, 3H), 3.75 (d, J = 6.9Hz, 2H), 4.82 (dq, J = 1.4, 8.6 Hz, 2H), 5.39 (m, 1H), 6.70 (d, J = 8.7 Hz, 2H), 6.93-6.97 (m, 3H), 7.64 (dd, J) = 2.4, 8.4Hz, 1 H), 8.10 (dd, J = 0.3, 2.1Hz, 1 H), IR (KBr): 3407, 2931, 2860, 1613, 1521, 1292, 1274, 1259, 1240, 1164, 1070, 823 cm · Ib-347 mp 154-156 ° C; Ή NMR (CDCl 3) δ 1.85 (t, J = 2.6 Hz, 3H), 1.99 (s, 6 H), 2.06 (s, 3 H), 3.33 (s, 3 H), 3.93 (q, J = 2.4 Hz, 2H) 6.40 (dd, J = 1.7, 3.2Hz, 1 H), 6.49 (dd, J = 0.9, 3.0Hz, 1 H), 6.76 (d, J = 8.7Hz, 2 H), 6.87 ( dd, J = 0.9, 8.7Hz, 1 H, 6.99 (brd, J = 7.5Hz, 2 H), 7.48 (dd, J = 0.9, 1.8Hz, 1 H), 7.58 (dd, J = 2.6, 8.6Hz, 1 H) ), 8.14 (dd, J = 0.6, 2.4 Hz, 1H) IR (KBr): 3410, 2989, 2934, 2860, 1610, 1520, 1278, 1242, 992, 822, 742 cm ^-1 Ib-348 mp 165-168 ° C; Ή NMR (CDCl 3) δ 1.85 (t, J = 2.4 Hz, 3H), 1.91 (t, J = 2.4 Hz, 3H), 1.99 (s, 6H), 2.05 (s, 3H), 3.32 (s, 3H) 3.93 (q, J = 2.4Hz, 2H), 5.01 (q, J = 2.4Hz, 2H), 6.76 (d, J = 8.7Hz, 2H), 6.89 (dd, J = 0.8, 8.6Hz, 1H) 6.99 (brd, J = 7.2 Hz, 2H), 7.58 (dd, J = 2.4, 8.4 Hz, 1H), 8.12 (dd, J = 0.6, 2.4 Hz, 1H), IR (KBr): 3393, 3338, 2923, 2862, 2237, 1612, 1604, 1521, 1279, 1243.996, 824 cm ¹ Ib-349 mp 172-173 ° C; Δ NMR (CDCl 3) δ 1.74 (s, 3H), 1.78 (s, 3H), 2.05 (s, 3H), 2.30 (s, 6H), 2.63 (s, 3H), 3.32 (s, 3H), 2.30 ( s, 6H), 3.74 (d, J = 6.6Hz, 2H), 5.39 (m, 1H), 6.70 (d, J = 8.7Hz, 2H), 6.96 (d, J = 6.6Hz, 2H), 7.27 ( dd, J = 8.4 and 0.6 Hz, 1H), 7.51 (dd, J = 8.1 and 2.1 Hz, 1H), 7.42 (dd, J = 2.1 and 0.9 Hz, 1H),; IR (CHCl 3): 3423, 3003, 2931, 28598, 1613, 1589, 1315, 14021, 1289, cm ^-1 . Ib-350 mp 183-184 ° C; @ 1 H NMR (CDCl3) .delta. 1.75 (s, 3H), 1.79 (s, 3H), 2.01 (s, 6H), 2.03 (s, 3H), 3.32 (s, 3H), 3.33 (s, 3H), 3.75 (d, J = 6.9 Hz, 2H), 5.40 (m, 1H), 6.72 (d, J = 8.7 Hz, 2H), 6.75 (d, J = 8.1 Hz, 2H), 7.98 (dd, J = 8.1 and 2.1 Hz, 1H), 8.17 (dd, J = 8.1 and 0.9 Hz, 1H), 8.70 (dd, J = 2.7 and 0.6 Hz, 1H); IR (CHCl 3): 3424, 3016, 2934, 2860, 1613, 1315, 1292, 1231, cm ^-1 . Ib-351 mp 148-149 ° C; Δ NMR (CDCl 3) δ 1.79 (s, 3H), 1.83 (s, 3H), 2.05 (s, 3H), 2.06 (s, 3H), 3.33 (s, 3H), 3.34 (s, 3H), 4.88 ( d, J = 6.9 Hz, 2H), 5.58 (m, 1H), 6.78 (d, J = 8.7 Hz, 2H), 6.84 (d, J = 8.4 Hz, 1H), 7.11 (d, J = 8.7 Hz, 2H), 7.56 (dd, J = 8.4, 2.4Hz, 1 H), 8.12 (d, J = 2.4Hz, 1 H) IR (KBr): 3393, 1603, 1520, 1492, 1459, 1399, 1373, 1357, 1282 , 1247, 1128, 1038, 1020, 982, 824 cm ¹ Ib-352 mp 106-107 ° C; Δ NMR (CDCl 3) δ 1.75 (s, 3H), 1.78 (s, 3H), 1.80 (s, 3H), 1.83 (s, 3H), 2.07 (s, 3H), 2.08 (s, 3H), 3.33 ( s, 3H), 3.34 (s, 3H), 3.75 (d, J = 6.6Hz, 2H), 4.88 (d, J = 7.2Hz, 2H), 5.38 (m, 1H), 5.58 (m, 1H), 6.70 (d, J = 8.4 Hz, 2H), 6.84 (d, J = 8.4 Hz, 1H), 7.12 (d, J = 8.4 Hz, 2H), 7.56 (dd, J = 8.4, 2.4 Hz, 1H), 8.12 (d, J = 2.4 Hz, 1H) IR (KBr) 3401, 1614, 1603, 1561, 1522, 1491, 1463, 1281, 1242, 1182, 1128, 1037, 985, 821 cm ^&lt; -1 ^&gt; Ib-353 mp 126-127 ° C; Δ NMR (CDCl 3) δ 1.49 (s, 3H), 1.67 (s, 3H), 1.80 (s, 3H), 1.83 (s, 3H), 2.02 (s, 3H), 2.07 (s, 3H), 2.81 ( d, J = 5.4Hz, 3H), 3.30 (s, 3H), 3.34 (s, 3H), 4.17 (q, J = 5.4Hz, 2H), 4.27 (d, J = 7.2Hz, 2H), 4.89 ( d, J = 7.2 Hz, 2H), 5.29 (m, 1H), 5.58 (m, 1H), 6.85 (d, J = 8.4 Hz, 1H), 7.32 (d, J = 4.2 Hz, 2H), 7.44 ( d, J = 4.2 Hz, 2H), 7.59 (dd, J = 8.4, 2.4 Hz, 1H), 8.11 (d, J = 2.4 Hz, 1H) IR (KBr): 3304, 1603, 1564, 1512, 1491, 1455, 1355, 1329, 1279, 1149, 1131, 1043, 1019, 986, 879, 823, δββαη ¹

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219 a a »« «· • • a • *

Table 125

Ib-354 m.p. 117-118 [deg.] C .; Ή NMR (300 MHz, CDCl 3) δ 1.12-1.30 (m, 2H), 1.30-1.48 (m, 2H), 1.62-1.75 (m, 2H), 1.80 (s, 3H), 1.83 (s, 3H), 1.75-1.84 (m, 2 H), 2.06 (s, 3 H), 2.07 (s, 3 H), 2.06-2.18 (m, 2 H), 3.33 (s, 3 H), 3.34 (s, 3 H), 3.30-3.37 ( m, 1H), 4.88 (d, J = 6.9Hz, 2H), 5.56-5.61 (m, IH), 6.65-6.72 (m, 2H), 6.84 (dd, J = 8.7, 0.9Hz, IH), 7.06 -7.13 (m, 2H), 7.56 (dd, J = 8.7, 2.4Hz, 1H), 8.11 (dd, J = 2.4, 0.9Hz, 1H). Ib-355 mp 108-110 ° C, Ή NMR (CDCl 3) δ 1.74 (s, 3H), 1.78 (s, 3H), 1.81 (s, 3H), 1.82 (s, 3H), 1.94 (s, 3H), 2.06 ( s, 3H), 2.26 (s, 3H), 3.32 (s, 3H), 3.33 (s, 3H), 3.75 (d, J = 6.9Hz, 2H), 4.87 (d, J = 7.2Hz, 2H), 5.40 (m, 1H), 5.57 (m, 1H), 6.65 (d, J = 8.4Hz, 2H), 6.72 (d, J = 8.4Hz, 2H), 7.14 (d, J = 8.4Hz, 2H), 7.37 (d, J = 8.4Hz, 1H). IR (KBr): 3417, 2930, 1613, 1595, 1520, 1429, 1391, 1297, 1281, 1246, 1133, 1101, 1038 cm -1. Ib-356 1.119-121 ° C, Ή NMR (CDCl 3) δ 1.74 (s, 3H), 1.78 (s, 3H), 1.79 (s, 3H), 1.82 (s, 3H), 2.06 (s, 3H), 2.07 (s, 3H), 2.25 (s, 3H), 3.33 (s, 3H), 3.35 (s, 3H), 3.75 (d, J = 6.6Hz, 2H), 4.91 (d, J = 6.6Hz, 2H) 5.39 (br, J = 6.6 Hz, 1H), 5.59 (br, J = 6.6 Hz, IH), 6.71 (d, J = 8.4 Hz, 2H), 7.13 (d, J = 8.4 Hz, 2H) 7.37 (d, J = 2.1Hz, IH); 7.94 (d, J = 2.1Hz; IH) Ib-357 mp 130-132 ° C, Ή NMR (CDCl 3) δ 1.74 (s, 3H), 1.79 (s, 6H), 1.82 (s, 3H), 1.94 (s, 3H), 2.06 (s, 6H), 3.33 ( s, 3H), 3.37 (s, 3H), 3.76 (d, J = 6.9Hz, 2H), 4.86 (d, J = 6.9Hz, 2H), 5.40 (m, 1H), 5.57 (m, 1H), 6.71-6.74 (m, 3H); 7.14 (d, J = 8.7Hz, 2H); 7.94 (s, 1H). IR (KBr): 3392, 2927, 1611, 1521, 1448, 1390, 1349, 1322, 1286, 1270, 1236, 1179, 1115, 1026 cm &lt; -1 &gt; Ib-358 mp 120-121 ° C; Ή NMR (CDCl 3) δ 1.74 (s, 3H), 1.78 (s, 3H), 2.06 (s, 3H), 2.07 (s, 3H); 2.63 (s, 3H); 3.33 (s, 6H); 3.75 (d, J = 9.6 Hz, 2H); 5.39 (m, 1H); 6.70 (d, J = 8.4 Hz, 2H) ), 7.12 (d, J = 8.4 Hz, 2H), 7.27 (d, J = 8.1 Hz, IH), 7.51 (dd, J = 8.1 Hz, 2.4Hz, IH), 8.42 (d, J = 2.4 Hz, IH) IR (KBr): 3379, 1614, 1587, 1523, 1459, 1395, 1351, 1319, 1286, 1136, 1109, 1038, 1016, 985, 818 cm @ -1. Ib-359 b. 1.163-164 ° C; Ή NMR (300 MHz, CDCl 3) δ 1.75 (s, 3H), 1.78 (s, 3H), 2.07 (s, 3H), 2.09 (s, 3H), 3.33 (s, 3H), 3.36 (s, 3H) 3.75 (d, J = 6.6Hz, 2H), 3.91 (t, J = 5.9Hz, 2H), 4.58 (brs, 1H), 5.35-5.42 (m, 2H), 6.49 (d, J = 8.3Hz) 1 H, 6.65-6.72 (m, 2H), 7.08-7.15 (m, 2H), 7.44 (dd, J = 8.3, 2.0 Hz, 1H), 8.06 (d, J = 2.0 Hz, 1H). Ib-360 mp 145-146 ° C; Δ NMR (300 MHz, CDCl 3) δ 1.79 (s, 3H), 2.06 (s, 3H), 2.08 (s, 3H), 3.35 (s, 3H), 3.78 (t, J = 5.6Hz, 2H), 3.88 (br s, IH), 4.53 (br s), 5.36-5.44 (m, IH), 6.61 (dd, J = 8.4, 0.75Hz, IH), 6.73-6.79 (m, IH), 6.926.98 (m) (2H), 7.45 (dd, J = 8.4, 2.1Hz, 1H), 8.04 (d, J = 2.1Hz, 1H). Ib-361 mp 143-144 ° C; Δ NMR (300 MHz, CDCl 3) δ 1.75 (s, 3H), 1.79 (s, 3H), 2.06 (s, 3H), 2.09 (s, 3H), 3.35 (s, 3H), 3.36 (s, 3H) 3.78 (t, J = 6.0Hz, 2H), 3.83-3.94 (m, 3H), 4.53 (brs, 1H), 5.34-5.44 (m, 2H), 6.48 (dd, J = 8.4, 0.9Hz, 1H), 6.73-6.79 (m, IH), 6.92-6.98 (m, 2H), 7.43 (dd, J = 8.4, 2.4Hz, 1H), 8.05 (dd, J = 2.4, 0.6Hz, IH). Ib-362 Ή NMR (300 MHz, CDCl 3) δ 1.20-1.35 (m, 3H), 1.35-1.48 (m, 2H), 1.77 (s, 3H), 1.82 (s, 3H), 1.60-1.96 (m, 3H), 2.04 (s, 3H), 2.09 (s, 3H), 2.04-2.15 (m, 2H), 3.34 (s, 3H), 3.36 (s, 3H), 3.53-3.64 (m, 1H), 4.64 (d, J = 6.9 Hz, 2H), 4.60-4.65 (m, IH), 5.54-5.60 (m, IH), 6.47 (d, J = 8.4Hz, IH), 6.96-7.09 (m, 3H), 7.41 (dd) J = 8.4, 2.2 Hz, 1H), 8.02 (d, J = 2.2 Hz, 1H).

220 «· ·· · · · ·

989 99 9

9 9 • 99 9 9

Table 126

Ib-363 mp 96-97 ° C; Δ NMR (CDCl 3) δ 1.74 (s, 3H), 1.79 (s, 6H), 1.82 (s, 3H), 2.05 (s, 6H), 2.18 (s, 3H), 3.74 (d, J = 6.6 Hz, 2H), 4.87 (d, J = 7.2 Hz, 2H), 5.39 (t, J = 6.9Hz, 1 H, 5.58 (t, J = 7.2Hz, 1 H), 6.70 (d, J = 8.4Hz, 2 H), 6.81 (d, J = 8.4Hz, 1 H), 6.96-6.99 (m, 3H), 7.57 (dd, J = 0.9, 8.7 Hz, 1H), 8.16 (d, J = 2.1 Hz, 1H); IR (KBr): 3345, 2972, 2913, 1613, 1560, 1522, 1490, 1466, 1281, 1240, 982, 827 cm &lt; -1 &gt;. Ib-364 mp 133-134 ° C; Ή NMR (CDCl 3) δ 1.79 (s, 3H), 1.82 (s, 3H), 2.05 (s, 6H), 2.18 (s, 3H), 4.17 (br s, 1H), 4.38 (s, 2H), 4.87 (d, J = 7.2 Hz, 2H), 5.58 (t, J = 7.2 Hz, 1H), 6.74 (d, J = 8.4Hz, 2H), 6.81 (dd, J = 0.6, 8.4Hz, 1H), 6.97-6.99 (m, 3H), 7.31-7.46 (m, 5H), 7.57 (dd, J = 2.7, 8.7Hz) (1H), 8.15 (dd, J = 0.6, 2.4 Hz, 1H); IR (KBr): 3357, 2962, 2922, 1614, 1526, 1491, 1465, 1359, 1280, 1241, 999, 828 cm @ -1. Ib-365 mp 89-91 ° C; Δ NMR (CDCl 3) δ 1.71 (s, 3H), 1.75 (s, 3H), 1.79 (s, 3H), 1.82 (s, 3H), 2.25 (s, 3H), 3.75 (d, J = 6.9Hz, 2H), 3.88 (s, 3H), 4.87 (d, J = 6.9 Hz, 2H), 5.37 (m, 1H), 5.58 (m, 1H), 6.74-6.84 (m, 4H), 7.2l (s, 1H), 7.417.45 (m, 2H), 7.76 (dd, J = 2.4, 8.4Hz, 1H), 8.19 (d, J = 2.4Hz, 1H); IR (CHCl 3): 3426, 2935, 2859, 1611, 1524, 1504, 1482, 1379, 1357, 1316, 1281, 1241, 1187, 1165, 1128, 1039, 979, 895CIO- ^1. Ib-366 mp 93-94 ° C; Δ NMR (CDCl 3) δ 1.25 (d, J = 6.3 Hz, 6 H), 1.79 (s, 3 H), 1.82 (s, 3 H), 2.24 (s, 3 H), 3.67 (m, 1H), 3.79 (s, 3H), 4.87 (d, J = 7.2Hz, 2H), 5.57 (m, 1H), 6.69 (d, J = 7.5Hz, 2H), 6.79 (s, 1H), 6.82 (d, J = 8.4Hz, 1H), 7.21 (s, 1H), 7.42 (d, J = 8.4Hz, 2H), 7.60 (dd, J = 2.4, 8.7Hz, 1H), 8.19 (d, J = 2.4Hz, 1H); IR (CHCl3): 3424, 2974, 2934, 2871, 1673, 1611, 1566, 1524, 1504, 1482, 1385, 1357, 1318, 1281, 1242, 1129, 1039, 979 cm @ -1. Ib-367 mp 105-108 ° C; Δ NMR (CDCl 3) δ 1.79 (s, 3H), 1.82 (s, 3H), 2.24 (s, 3H), 3.78 (s, 3H), 4.38 (s, 2H), 4.87 (d, J = 7.2 Hz, 2H), 5.57 (m, 1H), 6.73 (d, J = 8.4Hz, 2H), 6.79 (s, 1H), 6.82 (d, J = 8.4Hz, 1H), 7.20 (s, 1H), 7.28- 7.43 (m, 7H), 7.60 (dd, J = 2.4, 8.4 Hz, 1H), 8.18 (d, J = 2.4 Hz, 1H); IR (CHCl3): 3448, 3421, 2936, 2859, 1612, 1566, 1524, 1482, 1391, 1358, 1316, 1281, 1242, 1187, 1165, 1128, 1039, 979 cm &lt; -1 &gt; Ib-368 mp 112-113 ° C; Δ NMR (CDCl 3) δ 1.55-1.72 (m, 6H), 1.79 (s, 3H), 1.82 (s, 3H), 2.07-2.12 (m, 2H), 2.24 (s, 3H), 3.41 (m, 1 H) ), 3.79 (s, 3H), 3.96 (s, 4H), 4.87 (d, J = 6.6Hz, 2H), 5.57 (m, 1 H), 6.70-6.83 (m, 4H), 7.20 (s, 1 H) 7.42 (d, J = 8.4 Hz, 2H), 7.42 (d, J = 8.4 Hz, 2H), 7.60 (dd, J = 1.8 Hz, 1H), 8.18 (d, J = 1.8 Hz, 1H) ; IR (CHCl3): 3425, 2952, 2887, 1611, 1524, 1504, 1482, 1445, 1376, 1357, 1310, 1281, 1188, 1152, 1105, 1036, 977, 925, 001 ^. Ib-369 b. 1.141-142 ° C; Δ NMR (CDCl 3) δ 1.56 (m, 2H), 1.79 (s, 3H), 1.82 (s, 3H), 2.05-2.10 (m, 2H), 2.25 (s, 3H), 3.48-3.59 (m, 3H) 3.79 (s, 3H), 4.00-4.05 (m, 2H), 4.87 (d, J = 6.9Hz, 2H), 5.57 (m, 1H), 6.73-6.84 (m, 4H), 7.20 (s, 1H), 7.42 (d, J = 8.4Hz, 2H), 7.60 (dd, J = 2.4, 8.4Hz, 1H), 8.18 (d, J = 2.4Hz, 1H); IR (CHCl3): 3424, 2966, 2939, 2850, 1611, 1566, 1523, 1482, 1386, 1357, 1316, 1188, 1136, 1087, 1039, 982, 870 001 ^1; Ib-370 mp 83-86 ° C; Δ NMR (CDCl 3) δ 1.71 (s, 3H), 1.75 (s, 3H), 2.24 (s, 3H), 3.74-3.81 (m, 5H), 5.35-5.40 (m, 3H), 6.40 (m, 1 H) 6.48 (d, J = 8.7 Hz, 2H), 6.80 (s, 1H), 6.85 (d, J = 8.7 Hz, 2H), 7.21 (s, 1H), 7.42-7.48 (m, 3H), 7.62 (dd, J = 2.4, 8.4 Hz, 1H), 8.20 (d, J = 2.4 Hz, 1H); IR (CHCl): 3427, 2935, 2858, 1611, 1567, 1524, 1503, 1480, 1390, 1346, 1316, 1282, 1187, 1165, 1150, 1127, 1039, 1015, 992, 920 cm ^-1

tt fc • fcfc fcfcfc fcfc

221 · fc

Fc fc fc fc fc fc fc

Table 127

Ib-371 mp 100-101 ° C; @ 1 H NMR (CDCl3) .delta. 1.26 (d, J = 6.3 Hz, 6H), 2.24 (s, 3H), 3.67 (m, 1H), 3.79 (s, 3H), 5.39 (s, 2H), 6.40 (m) 6.49 (m, 1H); 6.70-6.73 (m, 2H); 6.79 (s, 1H); 6.84 (d, J = 8.4 Hz, 1H); 7.21 (s, 1H); 7.43 (d, 1H); J = 8.4 Hz, 2H), 7.48 (m, 1 H), 7.62 (dd, J = 2.4, 8.4 Hz, 1 H), 8.20 (d, J = 2.4 Hz, 1 H); IR (CHCl): 3424, 2967, 2934, 1611, 1567, 1524, 1479, 1384, 1346, 1318, 1282, 1243, 1187, 1151, 1127, 1039, 1015.992, 920 cm ^-1 Ib-372 mp 138-139 ° C; Δ NMR (CDCl 3) δ 1.56-1.84 (m, 6H), 2.09-2.12 (m, 2H), 2.24 (s, 3H), 3.42 (m, 1 H), 3.79 (s, 3H), 3.97 (s, 4H) ), 5.39 (s, 2H), 6.40 (m, 1H), 6.49 (d, J = 3.3 Hz, 1H), 6.72 (m, 2H), 6.79 (s, 1H), 6.85 (d, J = 8.7 Hz) 7.20 (d, J = 8.7 Hz, 2H), 7.47 (d, J = 1.8 Hz, 1H), 7.62 (dd, J = 2.7, 8.7 Hz, 1H), 8.20 (d, J = 2.7 Hz, 1 H); IR (CHCl3): 3425, 2952, 2886, 1611, 1568, 1524, 1504, 1480, 1446, 1375, 1346, 1311, 1282, 1188, 1151, 1105, 1037, 993, 924 cm-1; Ib-373 mp 128-130 ° C; Δ NMR (CDCl 3) δ 1.73 (s, 3H), 1.78 (s, 3H), 1.79 (s, 3H), 1.82 (s, 3H), 2.04 (s, 3H), 2.08 (s, 3H), 3.34 ( s, 3H), 3.54 (s, 3H), 3.75 (d, J = 6.3 Hz, 2H), 4.86 (d, J = 6.9 Hz, 2H), 5.39 (m, 1H), 5.56 (m, 1H), 6.72 (d, J = 8.4 Hz, 2H), 6.79 (dd, J = 8.7, 0.6 Hz, 1H), 7.11 (d, J = 8.4 Hz, 2H), 7.48 (dd, J = 8.7, 2.4 Hz, 1H) 8.04 (dd, J = 2.4, 0.6Hz, 1H); IR (KBr) 3420, 1730, 1612, 1603, 1561, 1521, 1490, 1461, 1277, 1223, 1120, 1002, 983, 823 cm ^&lt; -1 ^&gt; Ib-374 b. 1.172-173 ° C; @ 1 H NMR (CDCl3) .delta. 1.73 (s, 3H), 1.77 (s, 3H), 2.04 (s, 3H), 2.08 (s, 3H), 3.35 (s, 3H), 3.53 (s, 3H), 3.75 (d, J = 6.9 Hz, 2H), 5.38 (s, 2H), 5.39 (m, 1 H), 6.39 (dd, J = 3.3, 1.8 Hz, 1 H), 6.48 (d, J = 3.3 Hz, 1 H) 6.73 (d, J = 8.4Hz, 2H), 6.82 (dd, J = 8.4Hz, 0.9Hz, 1H), 7.11 (d, J = 8.4Hz, 2H), 7.47 (dd, J = 1.8, 0.9Hz, 1H) 7.50 (dd, J = 8.4, 2.4Hz, 1H), 8.06 (dd, J = 2.4, 0.9Hz, 1H); IR (KBr) 3415, 1730, 1610, 1562, 1520, 1490, 1452, 1346, 1278, 1224, 1121, 989, 825, 736 cm @ -1. Ib-375 b. 1.146-147 ° C; Δ NMR (CDCl 3) δ 1.75 (s, 3H), 1.78 (s, 3H), 1.79 (s, 3H), 1.83 (s, 3H), 1.99 (s, 6H), 2.02 (s, 3H), 2.12 ( s, 3H) 3.75 (d, J = 6.9 Hz, 2H), 3.80 (br s, 1H), 4.89 (d, J = 6.9 Hz, 2H), 5.39 (t, J = 6.9 Hz, 1H), 5.59 (t, J = 7.2 Hz, 1H), 6.75 (d, J = 8.7 Hz, 2H), 6.85 (d, J = 8.4 Hz, 1H), 6.91-6.99 (m, 2H), 7.45 (dd, J = 2.4, 8.4Hz, 1H); 8.01 (dd, J = 0.9, 2.1Hz, 1H); IR (KBr): 3395, 2970, 2911, 2855, 1613, 1603, 1519, 1376, 1277, 1185, 1126, 977, 804 cm · ¹ Ib-376 mp 187-188 ° C; Δ NMR (CDCl 3) δ 1.79 (s, 3H), 1.83 (s, 3H), 1.99 (s, 3H), 2.02 (s, 3H), 2.12 (s, 3H), 4.13 (s, 3H), 4.38 (s, 2H), 4.89 (d, J = 6.9 Hz, 2H), 5.59 (t, J = 7.2 Hz, 1H), 6.74 (d, J = 8.4 Hz, 2H), 6.85 (d, J = 8.4 Hz) 1 H, 6.93-6.96 (m, 2H), 7.31-7.46 (m, 6H), 8.01 (d, J = 1.8 Hz, 1H); IR (KBr): 3358, 2964, 2929, 1613, 1526, 1490, 1451, 1280, 1244, 1184, 1125, 997, 975, 804, 732 cm ^&lt; -1 ^&gt; Ib-377 mp 75-76 ° C; Δ NMR (CDCl 3) δ 1.73 (s, 3H), 1.77 (s, 3H), 1.80 (s, 3H), 1.83 (s, 3H), 2.01 (s, 3H), 2.07 (s, 3H), 2.11 ( s, 3H), 3.37 (s, 3H), 3.73 (d, J = 6.6 Hz, 2H), 4.09 (br s, 1H), 4.88 (d, J = 6.9 Hz, 2H), 5.38 (t, J = 6.6Hz, 1H), 5.59 (t, J = 7.2Hz, 1H), 6.52-6.56 (m, 2H), 6.84 (d, J = 7.5Hz, 1H), 6.85 (s, 1H), 6.96 (d, J = 7.8 Hz, 1H), 7.59 (dd, J = 2.4, 8.4 Hz, 1H), 8.14 (d, J = 1.8 Hz, 1H); IR (KBr): 3424, 3339, 2969, 2927, 1611, 1509, 1460, 1353, 1282, 1252, 1103, 984, 813 cm ^&lt; -1 ^&gt;

titi ti • * titi titi ··

422 ti ti · ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti

Table 128

Ib-378 m.p. 150-151 [deg.] C .; Δ NMR (CDCl 3) δ 1.80 (s, 3H), 1.83 (s, 3H), 2.01 (s, 3H), 2.06 (s, 3H), 2.11 (s, 3H), 3.37 (s, 3H), 4.36 ( s, 2H), 4.88 (d, J = 6.9 Hz, 2H), 5.59 (t, J = 7.2 Hz, 1H), 6.54-6.60 (m, 2H), 6.84 (d, J = 8.4 Hz, 1H), 6.84 (d, J), 6.96 (d, J = 8.1 Hz, 1H), 7.30-7.44 (m, 5H), 7.58 (dd, J = 2.4, 8.4Hz, 1H), 8.14 (dd, J = 0.9, 2.4Hz, 1 H); IR (KBr): 3412, 3272, 3018, 2927, 2858, 1611, 1517, 1459, 1375, 1355, 1317, 1283, 1243, 1106, 1050, 985 cm @ -1. Ib-379 mp 69-70 ° C; Ή NMR (CDCl 3) δ 1.74 (s, 3H), 1.78 (s, 3H), 1.80 (s, 3H), 1.83 (s, 3H), 2.13 (s, 3H), 2.15 (s, 3H), 3.38 ( s, 3H), 3.72 (d, J = 6.9 Hz, 2H), 4.88 (d, J = 6.9 Hz, 2H), 5.36 (t, J = 6.9 Hz, 1H), 5.58 (t, J = 7.2 Hz, 1H), 6.38-6.49 (m, 2H), 6.84 (d, J = 8.4Hz, 1H), 6.95 (s, 1H), 7.06 (dd, J = 8.1, 8.4Hz, 1H), 7.57 (dd, J) = 2.4, 8.4Hz, 1H), 8.13 (d, J = 1.8Hz, 1H); IR (KBr): 3416, 2972, 2930, 1627, 1522, 1462, 1376, 1269, 1240, 1171, 1098, 963, 832 cm @ -1. Ib-380 mp 156-157 ° C; Η NMR (CDCl 3) δ 1.80 (s, 3H), 1.83 (s, 3H), 2.13 (s, 3H), 2.14 (s, 3H), 3.38 (s, 3H), 4.36 (s, 2H), 4.89 (d, J = 7.2 Hz, 2H), 6.40-6.51 (m, 2H), 5.58 (t, J = 7.2 Hz, 1H), 6.84 (d, J = 8.4 Hz, 1H), 6.94 (s, 1H) 7.09 (dd, J = 8.1, 8.4Hz, 1H), 7.32-7.40 (m, 5H), 7.58 (dd, J = 2.4, 8.4Hz, 1H), 8.13 (dd, J = 0.6, 1.8Hz, 1H); IR (KBr): 3262, 3019, 2930, 1626, 1528, 1464, 1353, 1317, 1284, 1244, 1170, 1105, 986, 821 cm @ -1. Ib-381 mp 121-123 ° C; Ή NMR (CDCl 3) δ 1.74 (s, 3H), 1.77 (s, 3H), 1.80 (s, 3H), 1.83 (s, 3H), 1.97 (s, 3H), 2.00 (s, 3H), 2.07 ( s, 3H) 3.51 (s, 3H), 3.72 (d, J = 6.9 Hz, 2H), 4.88 (d, J = 6.9 Hz, 2H), 5.37 (m, 1H), 5.58 (m, 1H), 6.64 (d, J = 8.7 Hz, 2H), 6.85 (d, J = 8.4 Hz, 1H), 7.01-7.08 (m, 2H), 7.38 (dd, J = 8.4, 2.4 Hz, 1H), 7.96 (d) J = 2.4Hz, 1H); IR (KBr) 3391, 1713, 1613, 1602, 1524, 1487, 1437, 1298, 1276, 1243, 1222, 1122, 979 cm ^&lt; -1 ^&gt; Ib-382 b. 1.126-128 ° C; Ή NMR (CDCl 3) δ 1.74 (s, 3H), 1.77 (s, 3H), 1.97 (s, 3H), 2.00 (s, 3H), 2.07 (s, 3H), 3.51 (s, 3H), 3.72 ( d, J = 6.6 Hz, 2H), 5.37 (m, 1H), 5.39 (s, 2H), 6.41 (dd, J = 3.0, 1.8 Hz, 1H), 6.50 (brd, J = 3.0 Hz, 1H), 6.64 d J = 8.7 Hz, 2H), 6.89 (dd, J = 8.4, 0.6 Hz, 1H), 7.01-7.09 (m, 2H), 7.40 (dd, J = 8.4, 2.4 Hz, 1H), 7.48 (dd, J) = 1.8, 0.6Hz, 1H), 7.98 (dd, J = 2.4, 0.6Hz, 1H); IR (KBr) 3384, 1714, 1612, 1523, 1490, 1343, 1322, 1301, 1281, 1246, 1224, 1124, 990 cm @ -1. Ib-383 m.p. 161-163 [deg.] C .; Δ NMR (CDCl 3) δ 1.73 (s, 3H), 1.77 (s, 3H), 1.91 (t, J = 2.4 Hz, 3H), 1.96 (s, 3H), 1.99 (s, 3H), 2.07 (s, 3H), 3.51 (s, 3H), 3.72 (d, J = 6.6Hz, 2H), 5.01 (q, J = 2.4Hz, 2H), 5.37 (m, 1H), 6.65 (d, J = 9.0Hz, 2H), 6.90 (dd, J = 8.7, 0.9Hz, 1H), 7.01-7.08 (m, 2H), 7.40 (dd, J = 8.7, 2.4Hz, 1H), 7.97 (dd, J = 2.4, 0.9Hz) (1H); IR (KBr) 3385, 1725, 1613, 1603, 1525, 1488, 1344, 1329, 1303, 1281, 1246, 1221, 999 cm · Ib-384 oil, Ή NMR (CDCl 3) δ 1.78 (s, 3H), 1.82 (s, 3H), 2.30 (s, 3H), 2.44 (s, 3H), 4.64 (d, J = 6.6 Hz, 2H), 5.55 ( m, 1H), 6.99-7.12 (m, 3H), 7.17 (s, 1 H), 7.37 (s, 1 H), 7.53 (d, J = 1.2 Hz, 1 H), 9.07 (d, J = 1.2 Hz, 1 H) ) Ib-385 mp 93-94 ° C; 1 H NMR (CDCl 3) δ 1.77 (s, 3H), 1.81 (s, 3H), 2.28 (s, 3H), 2.40 (s, 3H), 4.05 (s, 3H), 4.64 (d, J = 6.9Hz) (2H), 5.55 (m, 1 H), 6.86 (d, J = 1.2 Hz, 1 H), 6.98-7.12 (m, 3 H), 7.26 (s, 1 H), 7.34 (s, 1 H), 8.87 (d, J = 1.2 Hz, 1H); IR (KBr) 1589, 1533, 1518, 1496, 1394, 1364, 1299, 1263, 1232, 1123, 1040, 997, 986, 872 cm &quot;

Table 129

Ib-386 mp 95-96 ° C; Δ NMR (CDCl 3) δ 1.77 (s, 3H), 1.81 (s, 3H), 2.28 (s, 3H), 2.38 (s, 3H), 3.17 (s, 6H), 4.64 (d, J = 6.9Hz, 2H), 5.55 (m, 1H), 6.53 (d, J = 1.2Hz, 1H), 6.98-7.14 (m, 4H), 7.29 (s, 1H), 8.69 (d, J = 1.2Hz, 1H); IR (KBr) 1591, 1512, 1417, 1405, 1299, 1278, 1261, 1228, 1123, 1000, 836, 827 cm &lt; -1 &gt; Ib-387 mp 88-90 ° C; Δ NMR (CDCl 3) δ 1.78 (s, 3H), 1.83 (s, 3H), 2.29 (s, 3H), 2.30 (s, 3H), 4.57 (d, J = 6.6 Hz, 2H), 5.55 (t, J = 6.6Hz, 1H), 6.99 (d, J = 8.4Hz, 2H), 7.12 (s, 1H), 7.20 (s, 1H), 7.28 (d, J = 8.4Hz, 2H), 8.79 (s, 2H), 9.22 (s, 1 H); IR (KBr) 1611, 1519, 1497, 1415, 1384, 1240, 1007, 820, 731 cm &lt; -1 &gt;. Ib-388 mp 97-98 ° C; Δ NMR (CDCl 3) δ 1.78 (s, 3H), 1.82 (s, 3H), 2.29 (s, 3H), 2.30 (s, 3H), 4.64 (d, J = 6.6 Hz, 2H), 5.55 (t, J = 6.6 Hz, 1H), 7.00-7.14 (m, 4H), 7.18 (s, 1 H), 8.78 (s, 2 H), 9.22 (s 1 H); IR (KBr) 1523, 1502, 1415, 1386, 1313, 1285, 1274, 1263, 1233, 1200, 1131, 995, 858 cm &lt; -1 &gt;. Ib-389 m.p. 163-166 [deg.] C .; Ή NMR (CDCl 3) δ 1.77 (s, 3H), 1.82 (s, 3H), 2.29 (s, 3H), 4.56 (d, J = 6.6Hz, 2H), 5.11 (tm, J = 6.6Hz, 1H) 6.98 (d, J = 8.7 Hz, 2H), 7.08 (s, 1H), 7.16 (s, 1H), 7.27 (d, J = 8.7 Hz, 2H), 8.35 (s, 2H); IR (KBr) 3393, 3315, 3196, 1639, 1605, 1595, 1518, 1480, 1236, 1002, 838, 802 cm &lt; -1 &gt;. Ib-390 m.p. 158-160 [deg.] C .; Δ NMR (CDCl 3) δ 1.77 (s, 3H), 1.82 (s, 3H), 2.28 (s, 3H), 2.29 (s, 3H), 4.64 (d, J = 6.6 Hz, 2H), 5.17 (s, 2H), 5.56 (t, J = 6.6 Hz, 1H), 6.98-7.16 (m, 5H), 8.35 (s, 2H); IR (KBr) 3334, 3187, 1655, 1598, 1522, 1486, 1296, 1269, 1230, 1125, 998 cm -1. Ib-391 m.p. 156-158 [deg.] C .; Δ NMR (CDCl 3) δ 1.75 (s, 3H), 1.77 (s, 6H), 1.82 (s, 3H), 2.28 (s, 3H), 2.30 (s, 3H), 4.05 (t, J = 6.0 Hz, 2H), 4.56 (t, J = 6.6 Hz, 1H), 5.11 (t, J = 5.4 Hz, 1H), 5.36 (t, J = 6.6 Hz, 1H), 5.54 (t, J = 6.6 Hz, 1H) 6.97 (d, J = 9.0 Hz, 2H), 7.08 (s, 1H), 7.15 (s, 1H), 7.27 (d, J = 9.0 Hz, 2H), 8.34 (s, 2H); IR (KBr) 3236, 1608, 1598, 1522, 1495, 1436, 1264, 1244, 1181, 998, 833, 803 cm -1. Ib-392 mp 105-106 ° C; Δ NMR (CDCl 3) δ 1.75 (s, 3H), 1.77 (s, 6H), 1.82 (s, 3H), 2.28 (s, 3H), 2.30 (s, 3H), 4.00-4.09 (m, 2H), 4.63 (d, J = 6.6 Hz, 2H), 5.14 (m, 1 H), 5.37 (m, 1 H), 5.55 (t, J = 6.6 Hz, 1 H), 6.98-7.17 (m 5 H), 8.34 (s, 2H); IR (KBr) 3254, 1607, 1524, 1495, 1440, 1300, 1271, 1235, 1129, 995 cm &^lt; -1 ^&gt;. Ib-393 b. 1.182-184 ° C; Δ NMR (CDCl 3) δ 1.74 (s, 3H), 1.77 (s, 3H), 2.29 (s, 6H), 4.05 (dd, J = 6.6, 5.7 Hz, 2H), 5.17 (brs, 1H), 5.37 ( tm, J = 6.6 Hz, 1H), 6.75 (d, J = 8.7 Hz, 2H), 7.07 (s, 1H), 7.14 (s, 1H), 7.15 (d, J = 8.7 Hz, 2H), 8.34 ( s, 2H); IR (KBr) 3443, 3327, 3245, 3110, 1631, 1602, 1525, 1493, 1440, 1301, 828, 802 cm @ -1. Ib-394 m.p. 160-162 [deg.] C .; Δ NMR (CDCl 3) δ 1.74 (s, 6H), 1.77 (s, 6H), 2.29 (s, 3H), 2.30 (s, 3H), 3.74 (d, J = 6.9 Hz, 2H), 4.05 (dd, J = 6.6, 6.0Hz, 2H), 5.15 (brs, 1H), 5.37 (m, 2H), 6.67 (d, J = 8.4Hz, 2H), 7.07 (s, 1H), 7.16 (s, 1H), 7.18 d J = 8.4 Hz, 2H), 8.34 (s, 2H); IR (KBr) 3423, 3240, 3104, 1612, 1598, 1525, 1496, 1436, 1321, 1262, 1187, 1087, 824.802 cm -1; Ib-395 m.p. 106-108 [deg.] C .; Δ NMR (CDCl 3) δ 1.72 (s, 6H), 1.74 (s, 9H), 1.77 (s, 3H), 2.29 (s, 3H), 2.32 (s, 3H), 3.91 (d, J = 5.7Hz, 4H), 4.04 (dd, J = 6.3, 5.7 Hz, 2H), 5.08 (m, IH), 5.27 (m, 2H), 5.37 (m, IH), 6.72 (brd, J = 8.7Hz, 2H), 7.07 (s, 1H); 7.17 (s, 1H); 7.21 (d, J = 8.7 Hz, 2H); 8.34 (s, 2H); IR (KBr) 3433, 3254, 3110, 1599, 1523, 1494, 1434, 1378, 1232, 1196, 1092, 817, 801 cm &lt; -1 &gt;

• ft · «··

22H ftft ft ft ft ft ft ft ft ft ft ft ft ft ft ft ft ft ft ft ft ft ft

Table 130

Ib-396 mp 84-86 ° C; Δ NMR (CDCl 3) δ 1.74 (s, 3H), 1.77 (s, 3H), 1.79 (s, 3H), 2.23 (s, 3H), 2.28 (s, 3H), 3.71 (d, J = 6.9Hz) (2H), 4.93 (d, J = 6.9 Hz, 2H), 5.325.61 (m, 2H), 6.36-6.48 (m, 2H), 7.05 (t, J = 8.4 Hz, 1H), 7.09 (s, 1H), 7.15 (s, 1H), 8.53 (s, 2H), IR (KBr) 3224, 3315, 2970, 2923, 1628, 1592, 1534, 1474, 1438, 1377, 1341, 1317, 1249, 1173, 1110 , 993 cm ¹ Ib-397 m.p. 150-152 [deg.] C .; Δ NMR (CDCl 3) δ 1.74 (s, 3H), 1.78 (s, 3H), 1.80 (s, 3H), 1.81 (s, 3H), 1.99 (s, 6H), 2.00 (s, 6H), 3.74 ( d, J = 6.9 Hz, 2H), 4.95 (d, J = 7.2 Hz, 2H), 5.37-5.42 (m, 1 H), 5.58-5.64 (m, 1 H), 6.68-6.71 (m, 2 H), 6.936 .97 (m, 2H), 8.36 (s, 2H). IR (KBr): 3360, 2973, 2928, 2857, 1610, 1587, 1519, 1436, 1406, 1379, 1310, 1245, 1181, 983 cm @ -1. Ib-398 m.p. 156-158 [deg.] C .; Δ NMR (CDCl 3) δ 1.60 (s, 3H), 1.75 (s, 3H), 1.77 (s, 3H), 1.82 (s, 3H), 1.97 (s, 6H), 2.03 (s, 6H), 4.08 (m, 2 H), 4.64 (d, J = 6.6 Hz, 2 H), 5.05-5.08 (m, 1 H), 5.30-5.41 (m, 1 H), 5.54-5.60 (m, 1 H), 6.81-6.84 ( m, 1H), 6.89 (dd, J = 1.8, 12.0Hz, 1 H), 7.05 (t, J = 8.7Hz, 1 H), 8.15 (s, 1 H), IR (KBr): 3320, 2971, 2931, 2850 , 1627, 1604, 1525, 1483, 1395, 1373, 1338, 1309, 1288, 1263, 1240, 1175, 1115, 1038 cm -1. Ib-399 m.p. 161-163 [deg.] C .; Δ NMR (CDCl 3) δ 1.77 (s, 3H), 1.82 (s, 3H), 1.97 (s, 6H), 2.02 (s, 6H), 4.64 (d, J = 6.6 Hz, 2H), 5.13 (br s) (2H), 5.54-5.60 (m, IH), 6.80-6.84 (m, IH), 6.88 (dd, J = 1.8, 11.7Hz, IH), 7.05 (t, J = 8.7Hz, IH), 8.16 ( IR (KBr): 3344, 3210, 2987, 2917, 2859, 1654, 1618, 1597, 1541, 1513, 1479, 1427, 1382, 1295, 1263, 1240, 1212, 1114, 993 cm -1. Ib-400 Δ NMR (300 MHz, CDCl 3) δ 1.75 (s, 3H), 1.77 (s, 6H), 1.82 (s, 3H), 2.05 (s, 3H), 2.12 (s, 3H), 3.34 (s, 3H) 3.39 (s, 3H), 4.06 (t, J = 6.0Hz, 2H), 4.65 (d, J = 6.9 Hz, 2 H), 5.18 (t, J = 5.3 Hz, 1 H), 5.35-5.42 (m, 1 H), 5.53-5.60 (m, 1 H), 7.08-6.95 (m, 3 H), 8.30 (s) , 2H). Ib-401 oil, Ή NMR (CDCl 3) δ 1.77 (s, 3H), 1.82 (s, 3H), 2.31 (s, 3H), 2.54 (s, 3H), 4.56 (d, J = 6.6 Hz, 2H), 5.54 ( t, J = 6.6 Hz, 1H), 6.98 (d, J = 8.4 Hz, 2H), 7.16 (s, 1H), 7.21 (t, J = 5.1 Hz, 1H), 7.28 (d, J = 8.4 Hz, 2H), 7.73 (s, 1 H), 8.85 (d, J = 5.1 Hz, 2 H). Ib-402 mp 93-94 ° C; Δ NMR (CDCl 3) δ 1.77 (s, 3H), 1.82 (s, 3H), 2.31 (s, 3H), 2.54 (s, 3H), 4.64 (d, J = 6.6 Hz, 2H), 5.55 (t, J = 6.6 Hz, 1H), 6.98-7.25 (m, 5H), 7.73 (s, 1 H), 8.85 (s, 1 H), 8.86 (s 1 H); IR (KBr) 1573, 1560, 1521, 1414, 1299, 1277, 1260, 1238, 1130, 997 cm &lt; -1 &gt;. Ib-403 b. 1.107-108 ° C; Δ NMR (CDCl 3) δ 1.74 (s, 3H), 1.77 (s, 3H), 1.81 (s, 3H), 1.83 (s, 3H), 2.32 (s, 3H), 2.39 (s, 3H), 3.67 ( br s, 1H), 3.74 (d, J = 6.8Hz, 2H), 5.10 (d, J = 7.1Hz, 2H), 5.37 (br t, J = 6.8Hz, 1H), 5.62 (br t, J = 7.1 Hz (1H), 6.67 (d, J = 8.5Hz, 2H), 7.02 (d, J = 9.0Hz, 1H), 7.17 (s, 1H), 7.20 (d, J = 8.5Hz, 2H), 7.33 (s, 1H), 7.52 (d, J = 9.0Hz, 1H). Ib-404 m.p. 149-151 [deg.] C .; Δ NMR (CDCl 3) δ 1.78 (s, 6H), 1.82 (s, 3H), 2.31 (s, 3H), 2.38 (s, 3H), 4.57 (d, J = 6.6 Hz, 2H), 5.54 (t, J = 6.6Hz, 1H), 6.99 (d, J = 9.0Hz, 2H), 7.20 (s, 1H), 7.27 (d, J = 9.0Hz, 2H), 7.34 (s, 1H), 7.58 (d, J = 9.0 Hz, 1H), 7.60 (d, J = 9.0 Hz, 1H); IR (KBr) 1610, 1572, 1517, 1496, 1421, 1411, 1249, 1179, 1142, 1012, 1004, 857, 841 cm @ -1.

»· Φφφ · φφ · *

225 • · · · φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ φ

Table 131

Ib-405 mp 94-94.5 ° C; Δ NMR (CDCl 3) δ 1.77 (s, 3H), 1.82 (s, 3H), 2.30 (s, 3H), 2.39 (s, 3H), 4.20 (s, 3H), 4.57 (d, J = 6.6 Hz, 2H), 5.54 (tm, J = 6.6 Hz, 1H), 6.98 (d, J = 8.7 Hz, 2H), 7.04 (d, J = 9.0 Hz, 1H), 7.18 (s, 1H), 7.28 (d, J = 8.7 Hz, 2H), 7.34 (s, 1 H), 7.53 (d, J = 9.0 Hz, 1 H); IR (KBr) 1610, 1592, 1518, 1464, 1415, 1295, 1235, 1175, 1107, 1016, 867, 830 cm &^lt; -1 ^&gt;. Ib-406 mp 165-167 ° C; Δ NMR (CDCl 3) δ 1.77 (s, 3H), 1.82 (s, 3H), 2.29 (s, 3H), 2.41 (s, 3H), 3.24 (s, 6H), 4.56 (d, J = 6.6Hz, 2H), 5.54 (tm, J = 6.6 Hz, 1H), 6.87 (d, J = 9.3 Hz, 1H), 6.97 (d, J = 9.0 Hz, 2H), 7.15 (s, 1H), 7.28 (d, J = 9.0 Hz, 2H), 7.36 (s, 1H); 7.38 (d, J = 9.3 Hz, 1H); IR (KBr) 1606, 1593, 1493, 1427, 1387, 1237, 1178, 1003, 847, 826 cm @ -1. Ib-407 mp 138-140 ° C; Δ NMR (CDCl 3) δ 1.78 (s, 3H), 1.82 (s, 3H), 2.30 (s, 3H), 2.38 (s, 3H), 4.64 (d, J = 6.6 Hz, 2H), 5.55 (t, J = 6.6 Hz, 1H), 7.00-7.13 (m, 3H), 7.19 (s, 1 H), 7.34 (s, 1 H), 7.56 (m, 1 H), 7.62 (m, 1 H); IR (KBr) 1518, 1496, 1414, 1385, 1299, 1266, 1233, 1127, 994, 851 cm &^lt; -1 ^&gt;. Ib-408 mp 91-92 ° C; Δ NMR (CDCl 3) δ 1.77 (s, 3H), 1.82 (s, 3H), 2.29 (s, 3H), 2.39 (s, 3H), 4.20 (s, 3H), 4.64 (d, J = 6.6 Hz, 2H), 5.55 (t, J = 6.6 Hz, 1H), 6.907.14 (m, 4H), 7.16 (s, 1H), 7.34 (s, 1H), 7.53 (d, J = 9.0 Hz, 1H); IR (KBr) 1593, 1519, 1496, 1469, 1417, 1294, 1274, 1263, 1231, 1126, 1010, 995, 845 cm &^lt; -1 ^&gt;. Ib-409 mp 132-134 ° C; Δ NMR (CDCl 3) δ 1.77 (s, 3H), 1.82 (s, 3H), 2.29 (s, 3H), 2.41 (s, 3H), 3.24 (s, 6H), 4.64 (d, J = 6.6 Hz, 2H), 5.55 (t, J = 6.6 Hz, 1H), 6.87 (d, J = 9.6 Hz, 1H), 6.97-7.15 (m, 4H), 7.36 (s, 1 H), 7.37 (d, J = 9.6) Hz, 1H); IR (KBr) 1597, 1547, 1519, 1495, 1422, 1404, 1297, 1272, 1233, 1197, 1133, 993, 849 cm &^lt; -1 ^&gt;. Ib-410 mp 197-200 ° C; Δ NMR (CDCl 3) δ 1.77 (s, 3H), 1.82 (s, 3H), 2.29 (s, 3H), 2.36 (s, 3H), 4.56 (d, J = 6.9 Hz, 2H), 4.82 (s, 2H), 5.54 (tm, J = 6.9 Hz, 1H), 6.83 (d, J = 9.0 Hz, 1H), 6.97 (d, J = 9.0 Hz, 2H), 7.16 (s, 1H), 7.27 (d, J = 9.0 Hz, 2H), 7.31 (s, 1H); 7.39 (d, J = 9.0 Hz, 1H); IR (KBr) 3486, 3370, 3308, 3164, 1649, 1625, 1606, 1516, 1495, 1461, 1234, 1216, 1173, 1011, 999, 982, 846, 835 cm ^1st Ib-411 mp 183-185 ° C; Δ NMR (CDCl 3) δ 1.77 (s, 3H), 1.82 (s, 3H), 2.28 (s, 3H), 2.36 (s, 3H), 4.64 (d, J = 6.6 Hz, 2H), 4.89 (brs, 2H), 5.55 (tm, J = 6.6 Hz, 1H), 6.85 (d, J = 9.0 Hz, 1H), 6.98-7.12 (m, 3H), 7.14 (s, 1H), 7.32 (s, 1H), 7.38 (d, J = 9.0 Hz, 1H); IR (KBr) 3486, 3368, 3308, 3161, 1649, 1624, 1519, 1497, 1461, 1261, 1123, 982, 844 cm ^1st Ib-412 mp 138-140 ° C; Δ NMR (CDCl 3) δ 1.76 (s, 6H), 1.77 (s, 3H), 1.82 (s, 3H), 2.29 (s, 3H), 2.39 (s, 3H), 4.03 (t, J = 6.3 Hz, 2H), 4.56 (d, J = 6.9 Hz, 2H), 4.77 (m, 1H), 5.38 (tm, J = 6.9 Hz, 1H), 5.54 (tm, J = 6.9 Hz, 1H), 6.70 (d, J = 9.0 Hz, 1H), 6.97 (d, J = 9.0 Hz, 2H), 7.15 (s, 1H), 7.28 (d, J = 9.0 Hz, 2H), 7.33 (s, 1H), 7.35 (d, J = 9.0 Hz, 1H); IR (KBr) 3213, 1605, 1530, 1492, 1234, 1180, 994, 841 cm &^lt; -1 ^&gt;. Ib-413 mp 113-115 ° C; @ 1 H NMR (CDCl3) .delta. 1.76 (s, 3H), 1.77 (s, 3H), 1.78 (s, 3H), 1.81 (s, 3H), 2.28 (s, 3H), 2.39 (s, 3H), 3.98 -4.15 (m, 2H), 4.64 (d, J = 6.9Hz, 2H), 4.76 (m, 1H), 5.38 (m, 1H), 5.55 (tm, J = 6.9Hz, 1H), 6.70 (d, J = 9.3 Hz, 1H), 6.98-7.15 (m, 4H), 7.33 (s, 1 H), 7.35 (d, J = 9.3 Hz, 1 H); IR (KBr) 3424, 3214, 1601, 1534, 1492, 1416, 1296, 1261, 1232, 1126, 983, 829 cm &^lt; -1 ^&gt;.

228 φ φ φ · · · φ φ • φ · · · · · φ φ

Table 132

Ib-414 mp 159-161 ° C; @ 1 H NMR (CDCl3) .delta. 1.76 (s, 3H), 1.78 (s, 3H), 2.29 (s, 3H), 2.38 (s, 3H), 4.03 (dd, J = 6.6, 5.7Hz, 2H), 4.91 (m, 1H), 5.38 (tm, J = 6.6 Hz, 1H), 6.71 (d, J = 9.0 Hz, 2H), 6.75 (d, J = 8.7 Hz, 2H), 7.15 (s, 1H), 7.17 (d, J = 8.7 Hz, 2H), 7.32 (s, 1H); 7.37 (d, J = 9.0 Hz, 1H); IR (KBr) 3440, 3363, 3220, 1621, 1599, 1531, 1491, 1458, 1410, 1279, 1181, 1140, 1045, 1026, 835 cm ^&lt; -1 ^&gt; Ib-415 mp 131-133 ° C; Δ NMR (CDCl 3) δ 1.74 (s, 3H), 1.76 (s, 3H), 1.77 (s, 6H), 2.31 (s, 3H), 2.38 (s, 3H), 3.74 (d, J = 6.9Hz, 2H), 4.03 (dd, J = 6.0, 6.0Hz, 2H), 4.87 (brs, 1H), 5.38 (m, 2H), 6.67 (d, J = 8.4Hz, 2H), 6.71 (d, J = 9.3) Hz, 1H), 7.15 (s, 1H), 7.19 (d, J = 8.4 Hz, 2H), 7.32 (s, 1H), 7.36 (d, J = 9.3 Hz, 1H); IR (KBr) 3385, 3207, 1609, 1529, 1493, 1457, 1186, 1045, 834 cm @ -1. Ib-416 b. 1.174-175 ° C; @ 1 H NMR (CDCl3) .delta. 1.72 (s, 6H), 1.74 (s, 3H), 1.75 (s, 3H), 1.76 (s, 3H), 1.78 (s, 3H), 2.33 (s, 3), 2.38 (s, 3H), 3.91 (d, J = 6.0 Hz, 4H), 4.03 (dd, J = 6.0, 6.0 Hz, 2H), 4.88 (m, 1H), 5.26 (m, 2H), 5.38 (m, 1H), 6.71 (d, J = 9.0 Hz, 1H), 6.75 (d, J = 9.0 Hz, 2H), 7.17 (s, 1H), 7.22 (d, J = 9.0 Hz, 2H), 7.32 (s, 1H), 7.37 (d, J = 9.0 Hz, 1H); IR (KBr) 3432, 3252, 3133, 1615, 1578, 1524, 1473, 1449, 1350, 1316, 1305, 1234, 1195, 1162, 1057, 854, 819 cm ^1st Ib-417 mp 224-227 ° C; 1 H NMR (CDCl 3) δ 1.77 (s, 3H); 1.82 (s. 3H); 1.95 (s. 6H); 1.96 (s. 6H); 4.64 (d, J = 6.6 Hz, 2H); 4.91 (br. S, 2H); 5.57 (m, IH); 6.75-7.07 (m. 4H); 7.20 (dd, J = 1.8, 9.0 Hz, 1H); IR (KBr): 3341, 3163, 1637, 1513, 1460, 1297, 1263, 1243, 1114, 1001 cm &^lt; -1 ^&gt;. Ib-418 mp 215-216 ° C; Ή NMR (CDCl 3) δ 1.77 (s, 6H); 1.79 (s. 3H); 1.82 (s. 3H); 1.95 (s. 6H); 1.97 (s. 6H); 4.02 (t, J = 6.3 Hz, 2H); 4.64 (d, J = 7.2 Hz, 2H); 4.84 (br. 1H); 5.39 (m, IH); 5.57 (m, IH); 6.74 (dd, J = 1.2, 9.0 Hz, 1H); 6.76 - 6.93 (m, 2H); 7.04 (t, J = 8.4 Hz, 1H); 7.15 (dd, J = 1.8, 9.0 Hz, 1H); IR (KBr): 3258, 2917, 1609, 1513, 1486, 1466, 1426, 1297, 1264, 1241, 1118 cm &^lt; -1 ^&gt;. Ib-419 mp 178-180 ° C; Δ NMR (CDCl 3) δ 1.74 (s, 3H), 1.78 (s, 3H), 1.82 (s, 3H), 1.85 (s, 3H), 1.95 (s, 6H), 1.98 (s, 6H), 3.4 ( br s, 1H) 3.75 (d, J = 6.9 Hz, 2H), 5.11 (d, J = 6.9 Hz, 2H), 5.40 (t, J = 6.9 Hz, 1H), 5.63 (d, J = 6.9 Hz) 1 H, 6.70-6.74 (m, 2H), 6.92-6.99 (m, 2H), 7.04 (d, J = 9.2 Hz, 1H), 7.32 (d, J = 9.2 Hz, 1H); IR (KBr): 3368, 2979, 2932, 2915, 1612, 1520, 1438, 1303, 1285, 966, 821, 529 cm &^lt; -1 ^&gt;. Ib-420 Δ NMR (300 MHz, CDCl 3) δ 1.77 (s, 6H), 1.79 (d, J = 1.2Hz, 3H), 1.82 (d, J = 0.9Hz, 3H), 2.04 (s, 3H), 2.12 (s) 3.35 (s, 3H); 4.65 (d, J = 6. 6 Hz, 2H); 4.81 (t, J = 6. 3 Hz); 1 H, 5.35-5.42 (m, 1 H), 5.53-5.60 (m, 1 H), 6.72 (d, J = 9.2 Hz, 1 H), 6.95-7.08 (m, 3 H), 7.29 (d, J = 9.2) Hz, 1H). Ib-421 mp 88-89 ° C; @ 1 H NMR (CDCl3) .delta. 1.78 (s, 3H), 1.82 (s, 3H), 2.31 (s, 3H), 2.40 (s, 3H), 4.57 (d, J = 6.6 Hz, 2H), 5.54 (t J = 6.6Hz, 1H), 6.98 (d, J = 9.0Hz, 2H), 7.19 (s, 1H), 7.28 (d, J = 9.0Hz, 2H), 7.35 (s, 1H), 8.53 (d) J = 2.7Hz, 1H), 8.68 (dd, J = 2.7, 1.2Hz, 1H), 8.78 (d, J = 1.2Hz, 1H); IR (KBr) 1606, 1574, 1516, 1496, 1469, 1386, 1241, 1178, 1145, 1011, 1002, 982, 840, 833 cm &^lt; -1 ^&gt;. Ib-422 mp 87-88 ° C; Δ NMR (CDCl 3) δ 1.77 (s, 3H), 1.82 (s, 3H), 2.31 (s, 3H), 2.40 (s, 3H), 4.64 (d, J = 6.6 Hz, 2H), 5.55 (t, J = 6.6Hz, 1H), 6.99-7.14 (m, 3H), 7.17 (s, 1 H), 7.35 (s, 1 H), 8.54 (m, 1 H), 8.68 (m, 1 H), 8.77 (m, 1 H) ; IR (KBr) 1517, 1501, 1476, 1447, 1397, 1387, 1315, 1297, 1265, 1234, 1198, 1127, 996, 849 cm &^lt; -1 ^&gt;.

·· · «·· • ·

22 ^.

► * · «·· ··

Table 133

Ib-423 mp 74-77 ° C; Δ NMR (CDCl 3) δ 1.77 (s, 3H), 1.82 (s, 3H), 2.29 (s, 3H), 2.37 (s, 3H), 4.56 (d, J = 6.9 Hz, 2H), 4.60 (s, 2H), 5.54 (tm, J = 6.9 Hz, 1H), 6.97 (d, J = 8.7 Hz, 2H), 7.14 (s, 1H), 7.27 (d, J = 8.7 Hz, 2H), 7.29 (s, 1 H, 8.10 (s, 1 H), 8.18 (s 1 H); IR (KBr) 3464, 3319, 3165, 1606, 1477, 1381, 1241, 1178, 1023, 1002, 839, 832 cm @ -1. Ib-424 mp 127-128 ° C; Δ NMR (CDCl 3) δ 1.77 (s, 3H), 1.81 (s, 3H), 2.28 (s, 3H), 2.37 (s, 3H), 4.62 (s, 2H), 4.63 (d, J = 6.6 Hz, 2H), 5.55 (t, J = 6.6 Hz, 1H), 6.98-7.12 (m, 3H), 7.13 (s, 1 H), 7.29 (s 1 H), 8.09 (d, J = 1.5 Hz, 1 H), 8.17 (d, J = 1.5 Hz, 1H); IR (KBr) 3426, 3306, 3189, 1641, 1580, 1536, 1517, 1498, 1482, 1393, 1292, 1281, 1265, 1231, 1121, 982 cm @ -1. Ib-425 m.p. 136-138 [deg.] C .; Δ NMR (CDCl 3) δ 1.77 (s, 3H), 1.82 (s, 3H), 2.28 (s, 3H), 2.38 (s, 3H), 3.74 (m, 1 H), 4.56 (d, J = 6.9Hz, 2H), 5.54 (tm, J = 6.9 Hz, 1H), 6.97 (d, J = 8.7 Hz, 2H), 7.13 (s, 1H), 7.27 (d, J = 8.7 Hz, 2H), 7.29 (s, 1H), 7.96 (d, J = 1.2 Hz, 2H), 8.16 (d, J = 1.2 Hz, 1H); IR (KBr) 3282, 1597, 1527, 1492, 1241, 1174, 1018, 885, 826 cm @ -1. Ib-426 m.p. 119-121 [deg.] C .; Δ NMR (CDCl 3) δ 1.77 (s, 3H), 1.81 (s, 3H), 2.28 (s, 3H), 2.38 (s, 3H), 3.74 (m, 1 H), 4.57 (d, J = 8.1 Hz, 1H), 4.63 (d, J = 6.6 Hz, 2H), 5.55 (t, J = 6.6 Hz, 1H), 6.98-7.12 (m, 3H), 7.11 (s, 1H), 7.29 (s, 1H), 7.96 (d, J = 1.5 Hz, 1H), 8.15 (d, J = 1.5 Hz, 1H); IR (KBr) 3424, 3275, 1598, 1528, 1495, 1280, 1265, 1173, 1018, 1007 cm @ -1. Ib-427 m.p. 134-136 [deg.] C .; Δ NMR (CDCl 3) δ 1.77 (s, 3H), 1.78 (s, 6H), 1.82 (s, 3H), 2.29 (s, 3H), 2.38 (s, 3H), 3.98 (t, J = 5.4Hz, 2H), 4.56 (d, J = 6.9 Hz, 2H), 5.36 (tm, J = 6.9 Hz, 1H), 5.54 (tm, J = 6.9 Hz, 1H), 6.97 (d, J = 8.7 Hz, 2H) 7.17 (d, J = 1.5 Hz, 1H), 7.19 (d, J = 8.7 Hz, 2H), 7.19 (d, J = 1.5 Hz, 1H), 7.19 (d, J = 1.5 Hz, 1H) ; IR (KBr) 3215, 1608, 1578, 1561, 1492, 1380, 1362, 1243, 1179, 1166, 1017, 1003, 830 cm -1. Ib-428 mp 99-100 ° C; Δ NMR (CDCl 3) δ 1.76 (s, 6H), 1.78 (s, 3H), 1.81 (s, 3H), 2.28 (s, 3H), 2.38 (s, 3H), 3.98 (dd, J = 6.6, 5.4) Hz, 2H), 4.59 (t, J = 6.6 Hz, 1H), 4.63 (d, J = 6.6 Hz, 1H), 5.36 (t, J = 6.6 Hz, 1H), 6.98- 7.12 (m, 3H), 7.12 (s, 1 H), 7.30 (s, 1 H), 7.98 (d, J = 1.5 Hz, 1 H), 8.18 (d, J = 1.5 Hz, 1 H); IR (KBr) 3239, 1578, 1565, 1492, 1390, 1362, 1303, 1277, 1261, 1122, 995, 873, 827 cm ^&lt; -1 ^&gt; Ib-429 mp 133-134 ° C; Δ NMR (CDCl 3) δ 1.74 (s, 3H), 1.76 (s, 3H), 1.77 (s, 3H), 1.78 (s, 3H), 2.31 (s, 3H), 2.38 (s, 3H), 3.73 ( d, J = 6.6 Hz, 2H), 3.97 (dd, J = 6.0, 6.0 Hz, 2H), 4.57 (m, 1H), 5.37 (m, 2H), 6.67 (d, J = 8.4 Hz, 2H), 7.14 (s, 1H), 7.19 (d, J = 8.4 Hz, 2H), 7.28 (s, 1H), 7.97 (d, J = 1.5 Hz, 1H), 8.19 (d, J = 1.5 Hz, 1H); IR (KBr) 3413, 3222, 1612, 1580, 1561, 1523, 1493, 1457, 1379, 1362, 1319, 1186, 1165, 1094, 1056, 1017, 822 cm ^&lt; -1 ^&gt; Ib-430 oil, Ή NMR (CDCl 3) δ 1.72 (s, 6H), 1.74 (s, 6H), 1.76 (s, 3H), 1.78 (s, 3H), 2.33 (s, 3H), 2.37 (s, 3H), 3.90 (d, J = 6.3 Hz, 4H), 3.97 (dd, J = 6.0, 5.1 Hz, 2H), 4.54 (m, 1H), 5.26 (m, 2H), 5.36 (m, 1H), 6.74 (d) J = 8.7Hz, 2H), 7.15 (s, 1H), 7.21 (d, J = 8.7Hz, 2H), 7.15 (s, 1H), 7.21 (d, J = 8.7Hz, 2H), 7.28 (s) (1H), 7.98 (d, J = 1.5 Hz, 1H) 8.19 (d, J = 1.5 Hz, 1H)

228 '· * · · «* · ·' '' '' '' '' '' '' '' ·

Table 134

Ib-431 mp 167-168 ° C; Δ NMR (CDCl 3) δ 1.75 (s, 3H), 1.78 (s, 3H), 1.81 (s, 3H), 1.84 (s, 3H), 1.95 (s, 6H), 1.98 (s, 6H), 3.63 ( br s, 1H), 3.74 (d, J = 6.6 Hz, 2H), 4.90 (d, J = 7.1 Hz, 2H), 5.39 (t, J = 6.6 Hz, 1H), 5.58 (d, J = 7.1 Hz) 1 H, 6.67-6.71 (m, 2H), 6.87-7.00 (m, 2H), 8.07 (d, J = 1.5 Hz, 1H), 8.35 (d, J = 1.5 Hz, 1H); IR (KBr): 3355, 2964, 2926, 2874, 1614, 1521, 1458, 1345, 1312, 1270, 1029, 977, 820 011 ^first Ib-432 mp 161-162 ° C; @ 1 H NMR (CDCl3) .delta. 1.77 (s, 3H); 1.82 (s. 3H); 1.94 (s. 6H); 1.97 (s. 6H); 4.64 (d, J = 6.3 Hz, 2H); 4.64 (br. S, 2H); 5.57 (m, IH); 6.74-7.07 (m. 3H); 7.98 (s, 1 H); 8.15 (s. 1H); IR (KBr): 3450, 3340, 2921, 1624, 1527, 1514, 1461, 1374, 1295, 1261, 1245, 1192, 1116 cm &^lt; -1 ^&gt;. Ib-433 mp 130-132 ° C; Ή NMR (CDCl 3) δ 1.77 (s, 6H); 1.80 (s. 3H); 1.82 (s. 3H); 1.94 (s. 6H); 1.98 (s. 6H); 3.98 (br t, J = 5.4 Hz, 2H); 4.56 (br. 1H); 4.64 (d, J = 6.6 Hz, 2H); 5.39 (m, IH); 5.57 (m, IH); 6.74-7.08 (m. 3H); 7.99 (s, 1 H); 8.02 (s, 1 H); IR (KBr): 3244, 2918, 1584, 1560, 1514, 1468, 1380, 1295, 1264, 1241, 1114 cm &lt; ^{-1 &gt};. Ib-434 amorphous; Δ NMR (CDCl 3) δ 1.77 (s, 3H), 1.80 (s, 3H), 1.96 (s, 6H), 1.98 (s, 6H), 3.5 (brs, 2H), 3.98 (m, 2H), 4.64 (m, 1 H), 5.39 (m, 1 H), 6.746.79 (m, 2 H), 6.84-6.99 (m, 2 H), 7.99 (d, J = 1.4 Hz, 1 H), 8.04 (d, J = 1.4) Hz, 1H); IR (KBr): 3334, 1620, 1588, 1519, 1462, 1276, 1161, 1024, 824, 525 cm @ ^-1 Ib-435 mp 180-182 ° C; @ 1 H NMR (CDCl3) .delta. 1.74 (s, 3H), 1.74 (s, 3H), 1.78 (s, 3H), 1.79 (s, 3H), 1.97 (s, 6H), 1.98 (s, 6H), 3.4 (br s, 1H), 3.74 (d, J = 6.9Hz, 2H), 3.98 (t, J = 6.0Hz, 2H), 4.50 (t, J = 5.1Hz, 1H), 5.36-5.41 (m, 2H) 6.66-6.72 (m, 2H); 6.86-7.02 (m, 2H); 8.00 (d, J = 1.4Hz, 1H); 8.02 (d, J = 1.4Hz, 1H); IR (CHC): 3439, 1613, 1585, 1519, 1468 cm ^-1 Ib-436 Δ NMR (300 MHz, CDCl 3) δ 1.77 (s, 6H), 1.79 (d, J = 0.9Hz, 3H), 1.81 (s, 3H), 2.04 (s, 3H), 2.08 (s, 3H), 3.34 (s, 3H), 3.41 (s, 3H), 3.99 (t, J = 5.3Hz, 2H), 4.64 (d, J = 6.9Hz, 2H), 4.58-4.67 (m, 1H), 5.34-5.42 ( m, 1H), 5.53-5.60 (m, 1H), 6.93-7.07 (m, 3H), 8.02 (d, J = 1.5Hz, 1H), 8.11 (d, J = 1.5Hz, 1H). Ib-437 foam; Δ NMR (CDCl 3) δ 2.21 (s, 3H), 2.28 (s, 3H), 6.34-6.49 (m, 2H), 6.80 (d, J = 2.1 Hz, 1H), 7.03-7.12 (m, 3H), 7.40 (d, J = 2.4 Hz, 1H), 7.61 (m, 1H); IR (KBr) 3414, 2862, 2589, 1652, 1601, 1541, 1492, 1430, 1330, 1186, 1222, 1186, 1147, 1123 , 1040, 998 cm ¹ Ib-438 foam; Δ NMR (CDCl 3) δ 2.12 (s, 3H), 2.78 (s, 3H), 6.61-6.81 (m, 3H), 6.99-7.06 (m, 3H), 7.41 (d, J = 2.1 Hz, 1H), 7.58 (dd, J = 2.4, 8.7 Hz, 1 H) IR (KBr): 3423, 2857, 2604, 1654, 1602, 1539, 1447, 1413, 1215, 1133, 1074 cm ^-1 Ib-439 foam; Δ NMR (CDCl 3) δ 1.73 (s, 3H), 1.79 (s, 3H), 2.14 (s, 3H), 2.28 (s, 3H), 3.71 (d, J = 6.6Hz, 2H), 5.33-5.39 ( m, 1H), 6.65-6.83 (m, 3 H), 6.99-7.09 (m, 3 H), 7.36 (d, J = 2.7 Hz, 1 H), 7.55-7.60 (m, 1 H) IR (KBr): 3431, 2923, 2550, 1654, 1604, 1480, 1455, 1376, 1357, 1284, 971 cm ¹ Ib-440 b. 1.193-195 ° C; Δ NMR (CDCl 3) δ 1.74 (s, 3H), 1.78 (s, 3H), 2.21 (s, 3H), 2.28 (s, 3H), 3.72 (d, J = 6.9Hz, 2H), 5.35 (t, J = 6.9 Hz, 1 H, 6.40 (dd, J = 12.3, 2.1 Hz, 1 H), 6.46 (dd, J = 8.4, 2.4 Hz, 1 H), 6.67 (dd, J = 9.3, 0.6 Hz, 1 H), 7.04 (t, J = 8.4 Hz, 1 H), 7.07 (s, 1H), 7.11 (s, 1 H), 7.39 (dd, J = 2.4, 0.6 Hz, 1 H), 7.56 (dd, J = 9.3, 2.4 Hz) (1H); IR (KBr): 3413, 3302, 1660, 1620, 1497, 1466, 1421, 1337, 1232, 1174, 835 cm ^&lt; -1 ^&gt;

0 · 0 · ·

229 ´ ··: 0 »0 tfc 0 0 0 0 0 0 0

Table 135

Ib-441 mp 247-249 ° C; Ή NMR (CDCl 3) δ 1.78 (s, 3H); 1.82 (s. 3H); 1.96 (s. 6H); 2.04 (s. 6H); 4.64 (d, J = 6.9 Hz, 2H); 5.58 (m, IH); 6.72 (d, J = 9.3 Hz, 1H); 6.806.92 (m. 2H); 7.05 (dt, J = 1.2, 8.4 Hz, 1H); 7.22 (d, J = 1.8 Hz, 1H); 7.35 (ddd, J = 1.8, 2.4, 9.3 Hz, 1H); IR (KBr): 3444, 2917, 1661, 1619, 1512, 1294, 1262 cm &^lt; -1 ^&gt;. Ib-442 mp 172-176 ° C; Ή NMR (CDCl 3) δ 1.78 (s, 3H); 1.82 (s. 3H); 1.95 (s. 6H); 2.05 (s. 6H); 4.64 (d, J = 6.9 Hz, 2H); 5.57 (m, IH); 6.75-7.25 (m. 5H); 10.81 (brs, 1H); IR (KBr): 2925, 1689, 1677, 1592, 1514, 1295, 1264, 1243, 1113, 1008 cm &^lt; -1 ^&gt;. Ib-443 mp 240-242 ° C; Ή NMR (CDCl 3) δ 1.77 (s, 3H); 1.82 (s. 3H); 1.96 (s. 6H); 2.06 (s. 6H); 4.64 (d, J = 6.3 Hz, 2H); 5.57 (m, IH); 6.74-7.09 (m. 3H); 7.22 (d, J = 1.2 Hz, 1H); 8.42 (d, J = 1.2 Hz, 1H); IR (KBr): 2916, 1655, 1616, 1512, 1261 cm &^lt; -1 ^&gt;. Ib-539 > HMR (CDCl3): δ 1.59 (3H, s), 1.74 (3H, s), 1.79 (3H, s), 1.83 (3H, s), 2.20 (3H, s), 2.28 (3H, s), 4.32 (2H, d, J 7.2Hz), 4.89 (2H, d, J 6.9Hz), 5.32 (1H, bt, J 7.2Hz), 5.58 (2H, bt, J 6.9Hz), 5.81 (2H, bs), 6.83 (1H, d, J 8.4Hz), 7.14 (2H, bs), 7.03-7.30 (3H), 7.60 (1H, dd, J 8.4Hz, 2.4Hz), 8.18 (1H, d, J 2.4Hz). Ib-540 > HNMR (CDCl3): δ 1.58 (3H, s), 1.73 (3H, s), 1.80 (3H, s), 2.20 (3H, s), 2.20 (3H, s), 2.33 (1H, bs), 4.25 (2H, bs), 4.30 (2H, d, J 6.9Hz), 4.88 (2H, d, J 6.9Hz), 5.30 (1H, bt, J 6.9Hz), 5.58 (2H, bt, J 6.9Hz), 5.90 (2H, bs), 6.83 (1H, d, J 8.4Hz), 6.95-7.30 (3H), 7.13 (2H, bs), 7.60 (1H, dd, J 8.4Hz, 2.4) Hz), 8.18 (1H, d, J 2.4 Hz). Ib-541 • HMR (CDCl3): δΗ 1.58 (3H, s), 1.73 (3H, s), 1.79 (3H, s), 1.82 (3H, s), 2.20 (3H, s), 2.27 (3H, s), 2.71 (4H, s), 4.29 (2H, d, J 7.2Hz), 4.88 (2H, d, J 6.9Hz), 5.30 (1H, bt, J 6.9Hz), 5.57 (2H, bt, J 7.2Hz), 5.80 (2H, bs,), 6.82 (1H, d, J 8.1Hz), 6.97-7.27 (3H), 7.13 (1H, d, J 2.4Hz), 7.60 (1H, dd, J 8.1Hz, 2.4Hz) 8.18 (1 H, bs). Ic-1 119-120 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.82 (3H, s), 2.17 (3H, s), 2.24 (3H, s), 4.61 (2H, d, J = 6.8) ), 4.63 (1H, s), 5.52 (1H, br t, J = 6.8), 5.71 (1H, s), 6.66 (1H, s), 6.76 (1H, dd, J = 2.2, 8.3), 6.80 ( 2H, d, J = 8.3), 6.86-6.91 (4H, m), 7.07 (1 H, s) Ic-2. oil, δ-NMR (CDCl 3) δ 1.75 (3H, s), 1.78 (3H, s), 2.17 (3H, s), 2.25 (3H, s), 3.87 (3H, s), 4.62 (2H, d, J = 6.6, 4.67 (1H, s), 5.56 (1H, brt, J = 6.6), 6.68 (1H, s), 6.79-6.93 (7H, m), 7.09 (1H, s) Ic-3 oil, δ-NMR (CDCl 3) δ 2.18 (3H, s), 2.22 (3H, s), 3.14 (3H, s), 5.16 (2H, s), 5.71 (1H, s), 6.77 (1H, dd, J = 2.0, 8.3), 6.81 (1 H, s), 6.93-6.99 (4 H, m), 7.10 (1 H, s), 7.22 (2 H, d, J = 9.0), 7.39-7.47 (5 H, m) Ic-4 oil, δ-NMR (CDCl 3) δ 2.19 (3H, s), 2.21 (3H, s), 3.11 (3H, s), 3.15 (3H, s), 5.15 (2H, s), 6.82 (1H, s) 6.95 (2H, d, J = 9.3), 7.10 (1 H, s), 7.11 (1 H, d, J = 8.3), 7.21 (1 H, dd, J = 2.2, 8.3), 7.23 (2 H, d, J = 9.3), 7.31 (1 H, d, J = 2.2), 7.377.49 (5 H, m) Ic-5 oil, δ-NMR (CDCl 3) δ 2.19 (3H, s), 2.20 (3H, s), 3.14 (3H, s), 3.91 (3H, s), 5.20 (2H, s), 6.79 (1H, dd, J = 2.0, 8.1), 6.81 (1 H, s), 6.86 (1 H, d, J = 2.0), 6.93 (1 H, d, J = 8.1), 6.95 (2 H, d, J = 9.0), 7.11 (1 H) (s), 7.22 (2H, d, J = 9.0), 7.32-7.49 (5 H, m) Ic-6 oil, δ-NMR (CDCl 3) δ 1.77 (3H, s), 1.82 (3H, s), 2.19 (3H, s), 2.21 (3H, s), 3.14 (3H, s), 3.22 (3H, s) 4.63 (2H, d, J = 6.8), 5.51 (1H, br, J = 6.8), 6.82 (1H, s), 6.95 (2H, d, J = 9.0), 7.04 (1H, d, J = 8.3), 7.11 (1 H, s), 7.21 (1 H, dd, J = 2.2, 8.3), 7.23 (2 H, d, J = 9.0), 7.29 (1 H, d, J = 2.2)

φ »····

28β ·· • 9 4 4

4 4 4 ·

4 9 4

4 Α

Table 136

Ic-7 oil, δ-NMR (CDCl 3) δ 1.76 (3H, s), 1.80 (3H, s), 2.20 (3H, s), 2.22 (3H, s), 3.15 (3H, s), 3.89 (3H, s) 4.63 (2H, d, J = 6.8), 5.57 (1H, br t, J = 6.8), 6.816.85 (3H, m), 6.93 (1H, d, J = 8.8), 6.96 (2H, d, J = 8.8), 7.13 (1 H, s), 7.22 (2 H, d, J = 8.8) Ic-8 162-163 ° C, δ-NMR (CDCl 3) δ 2.14 (3H, s), 2.26 (3H, s), 3.55 (2H, s), 3.89 (3H, s), 5.19 (2H, s), 6.64 (1H, d), 6.68 (2H, d, J = 8.8), 6.77 (1H, dd, J = 2.0, 8.7), 6.84 (2H, d, J = 8.8), 6.85 (1H, d, J = 2.0) 6.91 (1H, d, J = 8.7); 7.06 (1H, s); 7.31-7.49 (5H, m); Ic-9 111-112 ° C, 1 H-NMR (CDCl 3) δ 1.75 (3H, s), 1.79 (3H, s), 2.16 (3H, s), 2.27 (3H, s), 3.56 (2H, br s), 3.87 (3H, s), 4.62 (2 H, d, J = 6.8), 5.56 (1 H, br t, J = 6.8), 6.65 (1 H, s), 6.68 (2H, d, J = 9.0), 6.79-6.92 (5H, m), 7.08 (1 H, s) Ic-12 oil, δ-NMR (CDCl 3) δ 2.14 (3H, s), 2.28 (3H, s), 2.93 (6H, s), 3.89 (3H, s), 5.19 (2H, s), 6.64 (1H, s) 6.74 (2H, d, J = 9.0), 6.78 (1H, dd, J = 2.0, 8.3), 6.85 (1H, d, J = 2.0), 6.91 (1H, d, J = 8.3), 6.93 (2H) , d, J = 9.0), 7.31-7.49 (5 H, m) Ic-14 oil, δ-NMR (CDCl 3) δ 1.75 (3H, s), 1.79 (3H, s), 2.16 (3H, s), 2.28 (3H, s), 2.93 (6H, s), 3.87 (3H, s) 4.62 (2H, d, J = 6.8), 5.56 (1H, br t, J = 6.8), 6.65 (1H, s), 6.75 (2H, d, J = 9.0), 6.80-6.83 (2H, m) 6.90 (1H, d, J = 8.6); 6.93 (2H, d, J = 9.0); 7.08 (1H, s) Ic-16 119-120 ° C, δ-NMR (CDCl 3) δ 2.13 (3H, s), 2.27 (3H, s), 3.01 (6H, s), 6.78 (1 H, d, J = 9.3), 6.80 (2 H, d) J = 8.8), 6.89 (1 H, s), 7.16 (1 H, s), 7.22 (2 H, d, J = 8.8), 8.04 (1 H, dd, J = 2.7, 9.3), 8.39 (1 H, d, J = 2.7) Ic-17 80-82 ° C, @ 1 H-NMR (CDCl3) .delta. 2.17 (3H, s), 2.30 (3H, s), 2.98 (6H, s), 3.61 (2H, br s), 6.50 (1H, s), 6.55 (1H, dd, J = 2.7, 8.6), 6.77 (2H, d, J = 9.0), 6.81 (1H, d, J = 2.7), 6.82 (1H, d, J = 8.6), 7.07 (1H, s) 7.20 (2H, d, J = 9.0), Ic-18 141-142 ° C, Ή-NMR (CDCl 3) δ 2.21 (3H, s), 2.22 (3H, s), 3.00 (6H, s), 3.03 (3H, s), 6.41 (1H, br s), 6.71 (1H, s), 6.78 (2H, d, J = 8.8), 6.82 (1H, d, J = 8.8), 7.06 (1H, dd, J = 2.7, 8.8), 7.11 (1H, s), 7.21 ( 2H, d, J = 8.8. 7.39 (1H, d, J = 2.7) Ic-19 138-139 ° C, Ή-NMR (CDCl 3) δ 2.20 (3H, s), 2.22 (3H, s), 3.00 (6H, s), 6.72 (1H, s), 6.78 (2H, d, J = 8.8), 6.85 (1H, d, J = 8.8), 7.12 (1H, s), 7.21 (2H, d, J = 8.8), 7.35 (1H, dd, J = 2.7, 8.8), 7.77 (1 H, d, J = 2.7), 7.82 (1 H, br s), Ic-20 oil, δ-NMR (CDCl 3) δ 1.73 (3H, s), 1.77 (3H, s), 2.16 (3H, s), 2.31 (3H, s), 2.98 (6H, s), 3.67 (2H, d, J = 6.6), 5.33 (1 H, br t, J = 6.6), 6.48 (1 H, dd, J = 2.7, 8.8), 6.49 (1 H, s), 6.71 (1 H, d, J = 2.7), 6.77 ( 2H, d, J = 8.8), 6.85 (1H, d, J = 8.8), 7.07 (1H, s), 7.20 (2H, d, J = 8.8) lc-23 126-128 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.82 (3H, s), 2.26 (3H, s), 2.35 (3H, s), 4.58 (1 H, br s), 4.61 (2H, d, J = 6.8), 4.96 (2H, s), 5.52 (1 H, br t, J = 6.8), 5.72 (1 H, s), 6.75-6.81 (3H, m), 6.89-6.92 (4H) , m), 7.08 (1 H, s), 7.27 (1 H, s) lc-24 oil, .delta. 4.62 (2H, d, J = 6.8), 4.96 (2H, s), 5.50 (1H, br t, J = 6.8), 6.78 (2H, d, J = 9.0), 6.90 (2H, d, J = 9.0) 7.03 (1H, d, J = 8.5), 7.07 (1H, s), 7.20 (1H, dd, J = 2.2, 8.5), 7.28 (1H, s), 7.29 (1H, d, J 2.2) Ic-25 146-147 ° C, 1 H-NMR (CDCl 3) δ 1.75 (3H, s), 1.79 (3H, s), 2.25 (3H, s), 2.26 (3H, s), 3.86 (3H, s), 4.62 ( 2H, d, J = 6.8, 4.78 (1H, s), 5.02 (2H, s), 5.56 (1H, br t, J = 6.8), 6.79-6.82 (3H, m), 6.86 (2H, d, J = 8.5), 6.90 (1 H, d, J = 8.8), 7.04 (1 H, s), 7.35 (2 H, d, J = 8.5) Ic-32 123-124 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.81 (3H, s), 2.26 (6H, s9, 3.17 (3H, s), 3.21 (3H, s), 4.61 (2H) δ d, J = 6.8, 5.10 (2H, s), 5.50 (1 H, br t, J = 6.8), 6.76 (1 H, s), 7.02 (1 H, d, J = 8.3), 7.04 (1 H, s) 7.17 (1H, dd, J = 2.2, 8.3), 7.27 (1H, d, J = 2.2), 7.33 (2H, d, J = 8.8), 7.53 (2H, d, J = 8.8);

231 ft ft ft ft ft ft ft ft ft ft ft ft ft ft ft ft ft ft ft ft ft ft ft * ft ft ft ft ft ft ft ft ft

Table 137

Ic-33 125-127 ° C, 1 H-NMR (CDCl 3) δ 1.75 (3H, s), 1.79 (3H, s), 2.24 (3H, s), 2.35 (3H, s), 3.87 (3H, s), 4.21 ( 2H, s9, 4.61 (2H, d, J = 6.6), 5.56 (1H, brt, J = 6.6), 6.59 (2H, d, J = 8.8), 6.73 (2H, d, J = 8.8), 6.81 -6.85 (2 H, m), 6.92 (1 H, d, J = 8.8), 7.08 (1 H, s), 7.23 (1 H, s) Ic-35 141-142 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.82 (3H, s), 2.30 (3H, s), 2.40 (3H, s), 4.61 (2H, d, J = 6.8) ), 4.79 (IH, s), 5.53 (IH, br, J = 6.8), 5.70 (IH, s), 6.79 (IH, dd, J = 2.2, 8.3), 6.84 (2H, d, J = 8.8) 6.91 (IH, d, J = 8.3), 6.93 (IH, d, J = 2.2), 6.97 (IH, d, J = 16.1), 7.04 (IH, s), 7.18 (IH, d, J = 16.1), 7.43 (2H, d, J = 8.8), 7.46 (1H, s); Ic-38 140-142 ° C, 1 H-NMR (CDCl 3) δ 1.77 (3H, s), 1.82 (3H, s), 2.30 (3H, s), 2.41 (3H, s), 3.16 (3H, s), 3.22 ( 3H, s), 4.63 (2 H, d, J = 6.8), 5.51 (1 H, br t, J = 6.8), 7.02 (1 H, d, J = 15.4), 7.04 (1 H, d, J = 8.3) ), 7.05 (IH, s, J = 2.2, 8.3), 7.29 (2H, d, J = 8.8), 7.30 (IH, d, J = 2.2), 7.31 (IH, d, J = 15.4), 7.48 (1H, s), 7.57 (2H, d, J = 8.8); Ic-43 146-147 ° C, 1 H-NMR (CDCl 3) δ 1.75 (3H, s), 1.79 (3H, s), 2.25 (3H, s), 2.48 (3H, s), 3.88 (3H, s), 4.62 ( 2H, d, J = 6.8), 5.04 (IH, s), 5.56 (IH, brt, J = 6.8), 6.81-6.85 (4H, m), 6.92 (IH, d, J = 8.8), 7.10 (s) 1 H, s), 7.38 (1 H, s), 7.44 (2 H, d, J = 8.6) Ic-44 121-122 ° C, Ή-NMR (CDCl 3) δ 1.76 (3H, s), 1.79 (3H, s), 2.26 (3H, s), 2.49 (3H, s), 3.17 (3H, s), 3.88 ( 3H, s), 4.63 (2 H, d, J = 6.8), 5.56 (1 H, br t, J = 6.8), 6.81-6.85 (2 H, m), 6.93 (1 H, d, J = 8.8), 7.12 ( 1H, s), 7.29 (2H, d, J = 8.8), 7.40 (IH, s), 7.59 (2H, d, J = 8.8); Ic-47 oil, δ-NMR (CDCl 3) δ 1.76 (3H, s), 1.79 (3H, s9, 2.26 (3H, s), 2.29 (3H, s), 3.89 (3H, s), 4.64 (2H, d, J) = 6.6), 5.57 (1H, br, J = 6.6), 5.82 (IH, s), 6.856.88 (2H, m), 6.90 (2H, d, J = 8.8), 6.95 (IH, d, J) = 8.5), 7.14 (IH, s), 7.18 (IH, s), 7.81 (2H, d, J = 8.8). Ic-49 oil, δ-NMR (CDCl 3) δ 1.75 (3H, s), 1.79 (3H, s), 2.07 (IH, d, 3.7), 2.21 (3H, s), 2.28 (3H, s), 3.87 (3H, s) s), 4.62 (2 H, d, J = 6.8), 4.81 (2 H, d, J = 6.8), 5.56 (1 H, br t, J = 6.8), 6.81 (2 H, d, J = 8.8) 6.82-6.85 (2 H, m), 6.92 (1 H, d, J = 8.8), 7.02 (1 H, s), 7.25 (2 H, d, J = 8.8), 7.42 (1 H, s) Ie-4 170-170.5 ° C, δ-NMR (CDCl 3) δ 5.15 (2H, s), 5.75 (1H, s), 6.94 (1H, dd, J = 0.7, 8.5), 6.98 (2H, m), 7.06-7.16 (5H, m), 7.37-7.44 (5H, m), 7.83 (1 H, dd, J = 2.4, 8.5), 8.34 (1 H, dd, J = 0.7, 2.4) Ie-5 122-122.5 ° C Ie-6 175-176 ° C, 1 H-NMR (CDCl 3) δ 2.38 (3H, s), 5.11 (2H, s), 5.75 (1H, s), 6.94 (1H, d, J = 8.3), 6.98 (2H, m) 7.02-7.17 (5H, m), 7.22 (2 H, d, J = 8.1), 7.32 (2 H, d, J = 8.1), 7.83 (1 H, dd, J = 2.4, 8.6), 8.34 (1 H, d, J = 2.4) Ie-7 144.5-145.5 ° C, Ή-NMR (CDCl 3) δ 2.37 (3H, s), 3.11 (3H, s), 5.12 (2H, s), 6.96 (IH, d, J = 8.6), 7.10-7.15 (5H) (m), 7.21 (2H, d, J = 8.1), 7.33 (2H, d, J = 8.1), 7.39 (IH, dd, J = 2.2, 8.6), 7.47 (IH, d, J = 2.2), 7.83 (IH, d, J = 2.7, 8.6), 8.33 (IH, d, J = 2.7) Ie-8 125-127 ° C, δ-NMR (CDCl 3) δ 1.76 (3H, s), 1.81 (3H, s), 4.61 (2H, d, J = 6.8), 5.51 (1H, br t, J = 6.8), 5.76 (IH, d), 6.91-7.01 (3H, m), 7.06-7.16 (5H, m), 7.83 (IH, dd, J = 2.4, 8.6), 8.34 (IH, dd, J = 0.7, 2.4) Ie-9 127-128 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.81 (3H, s), 3.22 (3H, s), 4.62 (2H, d, J = 6.8), 5.48 (IH, br) t, J = 6.8, 6.96 (1H, dd, J = 0.7, 8.6), 7.06-7.15 (5H, m), 7.40 (IH, dd, J = 2.2, 8.6), 7.46 (IH, d, J 2.2), 7.83 (IH, dd, J = 2.4, 8.6), 8.33 (IH, dd, J = 0.7, 2.4) Ie-13 153-154 ° C, Ή-NMR (CDCl 3) δ 2.25 (3H, s), 3.10 (3H, s), 3.78 (3H, s), 5.16 (2H, s), 7.13 (2H, s), 7.19- 7.25 (4H, m), 7.36-7.48 (7Hs, m)

· · · · · · · · · · · · · · · · · · · · · · · · · · · ·

232 *

Table 138

Ie-14 oil, δ-NMR (CDCl 3) δ 2.23 (3H, s), 2.39 (3H, s), 3.77 (3H, s), 5.09 (2H, s), 5.74 (1H, s), 6.69 (1H, dd, J = 1.8.8.5), 6.82 (1H, d, J = 1.8), 6.98 (1H, d, J = 8.5), 7.187.43 (9H, m). Ie-15 166-167 ° C, δ-NMR (CDCl 3) δ 2.25 (3H, s), 2.38 (3H, s), 3.09 (3H, s), 3.78 (3H, s), 5.11 (2H, s), 7.12 ( 2H, s), 7.15-7.44 (10 H, m) Ie-17 132-133 ° C, Ή-NMR (CDCl 3) δ 2.25 (3H, s), 3.10 (3H, s), 3.79 (3H, s), 3.83 (3H, s), 5.16 (2H, s), 6.91 ( 2H, d, J = 9.1), 6.94-7.23 (5 H, m), 7.36-7.48 (5 H, m) Ie-18 oil, δ-NMR (CDCl 3) δ 2.24 (3H, s), 2.39 (3H, s), 3.78 (3H, s), 3.83 (3H, s), 5.09 (2H, s), 5.71 (1H, d, J = 1.8), 6.68 (1H, dd, J = 1.8, 7.9), 6.82 (1H, d, J = 1.8), 6.90 (2H, d, J = 1.8), 6.98 (1H, d, J = 7.9) 7.16 (2H, d, J = 1.8); 7.23 (2H, d, J = 7.9); 7.33 (2H, d, J = 7.9); Ie-19 113-114 ° C, δ-NMR (CDCl 3) δ 2.24 (3H, s), 2.38 (3H, s), 3.09 (3H, s), 3.78 (3H, s), 3.83 (3H, s), 5.11 ( 2H, s), 6.91 (2H, d, J = 8.5), 7.34 (2H, d, J = 8.5) Ie-23 Mp 157-158 ° C Ie-24 114-116 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.82 (3H, s), 2.23 (3H, s), 3.78 (3H, s), 4.60 (2H, d, J = 6.8) 5.57 (1H, br, J = 6.8), 5.74 (1H, s), 6.67 (1H, dd, J = 2.0, 8.3), 6.79 (1H, d, J = 2.0), 6.91 (1H, d) J = 8.3, 7.07 (1H, dd, J = 8.3, 9.3), 7.21 (1H, dd, J = 4.6, 8.3) Ie-25 107-108 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.81 (3H, s), 2.25 (3H, s), 3.21 (3H, s), 3.79 (3H, s), 4.62 ( 2H, d, J = 6.6), 5.50 (1 H, br t, J = 6.6), 7.03-7.23 (7H, m) Ie-27 177-178 ° C, Ή-NMR (CDCl 3) δ 2.24 (3H, s), 3.10 (3H, s), 3.92 (3H, s), 5.16 (2H, s), 6.99-7.49 (11H, m), 7.66 (2 H, d, J = 7.9) Ie-28 170-172 ° C, δ-NMR (CDCl 3) δ 2.22 (3H, s), 2.39 (3H, s), 3.92 (3H, s), 5.09 (2H, s), 5.71 (1H, s), 6.71 ( 1H, dd, J = 1.8, 7.9), 6.84 (1H, d, J = 1.8), 6.98 (1H, d, J = 7.9), 7.03 (2H, d, J = 7.3), 7.23 (2H, d, J = 7.9), 7.29-7.36 (3 H, m), 7.67 (2H, dd, J = 1.2, 8.5) Ie-29 169-170 ° C, Ή-NMR (CDCl 3) δ 2.24 (3H, s), 2.38 (3H, s), 3.10 (3H, s), 3.92 (3H, s), 5.11 (2H, s), 7.37 (10H, m); 7.66 (2 H, d, J = 7.9) Ie-31 150-151 ° C, δ-NMR (CDCl 3) δ 2.22 (3H, s), 3.10 (3H, s), 3.81 (3H, s), 3.88 (3H, s), 5.15 (2H, s), 6.87 ( 1H, s), 6.89 (2H, d J = 9.1), 7.09 (1H, d, J = 8.5), 7.14 (1H, dd, J = 1.8, 8.5), 7.24 (1H, d, J = 1.8), 7.36-7.53 (5H, m); 7.55 (2 H, d, J = 9.1) Ie-32 175-176 ° C, Ή-NMR (CDCl 3) δ 2.20 (3H, s), 2.39 (3H, s), 3.81 (3H, s), 3.88 (3H, s), 5.09 (2H, s), 5.68 ( 1 H, s), 6.70 (1 H, dd, J = 1.8, 7.9), 6.83 (1 H, d, J = 1.8), 6.85 (1 H, br s), 6.88 (2 H, d, J = 9.2), 6.97 (1 H, d, J = 7.9), 7.23 (2 H, d, J = 7.9), 7.34 (2 H, d, J = 7.9), 7.55 (2 H, d, J = 9.2) Ie-33 176-177 ° C, δ-NMR (CDCl 3) δ 2.22 (3H, s), 2.37 (3H, s), 3.09 (3H, s), 3.81 (3H, s), 3.88 (3H, s), 5.10 ( 2H, s), 6.87 (1 H, s), 6.89 (2 H, d, J = 8.5), 7.09 (1 H, d, J = 8.5), 7.14 (1 H, dd, J = 1.8, 8.5), 7.22 (2H) J = 8.5, 7.23 (1H, s), 7.34 (2H, d, J = 8.5), 7.55 (2H, d, J = 8.5). Ie-38 188-189 ° C, Ή-NMR (CDCl 3) δ 2.21 (3H, s), 2.39 (3H, s), 3.89 (3H, s), 5.09 (2H, s), 5.68 (1H, s), 6.70 ( 1 H, dd, J = 1.8, 7.9), 6.83 (1 H, d, J = 1.8), 6.91-7.06 (4H, m), 7.23 (2 H, d, J = 8.5), 7.34 (2 H, d, J = 8.5), 7.56-7.65 (2 H, m) Ie-39 194-195 ° C, Ή-NMR (CDCl 3) δ 2.23 (3H, s), 2.38 (3H, s), 3.09 (3H, s), 3.89 (3H, s), 5.11 (2H, s), 6.94- 7.21 (5H, m), 7.22 (2H, d, J = 1.8), 7.23 (1 H, s), 7.35 (2 H, d, J = 7.9), 7.57-7.63 (2 H, m) Ie-40 159-160 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.82 (3H, s), 2.21 (3H, s), 3.89 (3H, s), 4.60 (2H, d, J = 6.7) 5.52 (1H, t, J = 6.7), 5.71 (1H, s), 6.68 (1H, dd, J = 1.8, 8.5), 6.81 (1H, d, J = 1.8), 6.90 (1H, d, J = 8.5), 7.02 (2 H, t, J = 8.5), 7.57-7.65 (2 H, m)

• • •

233 .:

• · · · · · · · · ·

Table 139

Ie-41 142-143 ° C, 1 H-NMR (CDCl 3) δ 1.76 (3H, s), 1.81 (3H, s), 2.24 (3H, s), 3.21 (3H, s), 3.89 (3H, s), 4.62 ( 2H, d, J = 7.3., 5.50 (1H, t, J = 7.3), 6.94 (1H, s), 6.99-7.08 (3H, m), 7.13 (1H, dd, J = 2.4, 8.5), 7.22; (1H, d, J = 2.4), 7.56-7.65 (2 H, m) If-10 151-152 ° C, δ-NMR (CDCl 3) δ 2.18 (3H, s), 3.09 (3H, s), 3.75-3.81 (8H, m), 3.83 (3H, s), 5.14 (2H, s), 7.08 (1 H, d, J = 8.5), 7.11 (1 H, dd, J = 1.7, 8.5), 7.21 (1 H, d, J = 1.7), 7.35-7.47 (5H, m) If-14 140-141 ° C, δ-NMR (CDCl 3) δ 2.18 (3H, s), 2.36 (3H, s), 2.48 (4H, t, J = 5.5), 3.09 (3H, s), 3.83 (3H, s) 3.87 (4H, t, J = 5.5), 5.14 (2H, s), 7.07 (1 H, d, J = 8.5), 7.11 (1 H, dd, J = 1.8, 8.5), 7.21 (1 H, d, J = 1.8), 7.33 - 7.49 (5H, m) If-18 152-153 ° C, δ-NMR (CDCl 3) δ 2.20 (3H, s), 3.09 (3H, s), 3.26 (4H, t, J = 5.5), 3.86 (3H, s), 4.01 (4H, t, J = 5.5), 5.14 (2 H, s), 6.90 (1 H, d, J = 7.3), 7.00 (2 H, d, J = 7.3), 7.08 (1 H) δ d, J = 8.5), 7.12 (1H, dd, J = 1.8, 8.5), 7.21-7.49 (8H, m). If-26 195-197 ° C, Ή-NMR (CDCl 3) δ 2.44 (3H, s), 3.12 (3H, s), 4.05 (3H, s), 5.18 (2H, s), 7.14-7.21 (2H, m), 7.28 (1 H, m), 7.38-7.48 (5 H, m), 8.17 (1 H, s), 9.22 (1 H, s) If-29 122.5-123.5 ° C. Ή NMR (CDCl 3) δ 1.74 (s, 3H), 1.78 (s, 6H), 1.81 (s, 3H), 2.36 (s, 3H), 2.57 (brs, 3H), 3.74 (d, J = 6.9Hz, 2H), 4.88 (d, J = 6.9Hz, 2H), 5.37 (br t, J = 6.9 Hz, 1 H), 5.56 (br t, J = 6.9 Hz, 1 H), 6.68 (d, J = 8.7 Hz, 2 H), 6.84 (dd, J = 0.6, 8.7, 1 H) 7.19 (d, J = 8.7 Hz, 2 H), 7.43 (br s, 1 H), 7.83 (dd, J = 2.4, 8.7 Hz, 1 H), 8.38 (dd, J = 0.6, 2.4 Hz, 1 H) If-30 b. 1.122.5-123.5 ° C, Ή NMR (CDCl 3) δ 1.78 (s, 3H), 1.81 (s, 3H), 2.37 (s, 3H), 2.58 (br s, 3H), 4.88 (d, J = 7.2Hz, 2H), 5.56 (br t, J = 7.2Hz, 1H), 6.77 (d, J = 8.4Hz, 2H), 6.85 (dd, J) = 0.6, 8.4, 1H), 7.16 (d, J = 8.4Hz, 2H), 7.45 (brs, 1H), 7.84 (dd, J = 2.4, 8.4Hz, 1H), 8.38 (dd, J = 0.6, 2.4 Hz, 1H) Ig-1 mp 176-177 ° C; Ή NMR (CDCl 3) δ 1.80 (s, 3H); 1.83 (s. 3H); 1.98 (s. 6H); 2.00 (s, 6H); 4.51 (br. S, 2H); 4.88 (d, J = 6.9 Hz, 2H); 5.90 (m, IH); 6.63 (m, IH); 6.85 (ddd, J = 0.9, 1.5, 8.4 Hz, 1H); 7.29 (ddd, J = 2.1, 4.2, 8.4 Hz, 1H); 7.39 (ddd, J = 1.2, 2.4, 8.4 Hz, 1H); 7.90 (m, IH); 7.97 (m, IH); IR (KBr): 3464, 3302, 3164, 2916, 1638, 1603, 1512, 1491, 1459, 1385, 1360, 1300, 1279, 1242 cm &lt; -1 &gt;. Ig-2 mp 162-164 ° C; Ή NMR (CDCl 3) δ 1.75 (s, 3H); 1.78 (s. 3H); 1.80 (s. 3H); 1.83 (s, 3H); 1.98 (s. 6H); 2.02 (s. 6H); 3.91 (t, J = 5.7 Hz, 2H); 4.51 (br. T, 1H); 4.88 (d, J = 7.2 Hz, 2H); 5.38 (m, IH); 5.59 (m, IH); 6.50 (m, IH); 6.85 (ddd, J = 0.9, 1.5, 8.7 Hz, 1H); 7.27 (ddd, J = 2.1, 4.2, 8.7 Hz, 1H); 7.40 (ddd, J = 2.4, 3.3, 8.4 Hz, 1H); 7.92 (m, IH); 7.98 (dt, J = 0.9, 2.4 Hz, 1H); IR (KBr): 3420, 3242, 2913, 1605, 1503, 1462, 1378, 1350, 1277, 1240 cm -1. Ig-3 Δ NMR (300 MHz, CDCl 3) δ 1.80 (s, 3H), 1.83 (s, 3H), 2.07 (s, 3H), 2.09 (s, 3H), 3.34 (s, 3H), 4.59 (br, 2H), 4.89 (d, J = 7.2Hz, 2H), 5.545.62 (m, 1H), 6.62 (d, J = 8.4 Hz, 1 H), 6.84 (dd, J = 8.4, 0.7 Hz, 1 H), 7.45 (dd, J = 8.4, 2.2 Hz, 1 H, 7.54 (dd, J = 8.4 Hz, 1 H), 8.04 (d, J = 2.2 Hz, 1 H), 8.10 (dd, J = 2.5, 0.7 Hz, 1 H) Ig-4 Ή NMR (300 MHz, CDCl 3) δ 1.76 (s, 3H), 1.78 (d, J = 0.9Hz, 3H), 1.80 (d, J) = 0.9 Hz, 3 H), 1.83 (d, J = 0.9 Hz, 3 H), 2.07 (s, 3 H), 2.10 (s, 3 H), 3.34 (s, 3 H), 3.36 (s, 3 H), 3.91 (t J = 6.0 Hz (2H), 4.58 (br s, IH), 4.88 (d, J = 6.9Hz, 2H), 5.34-5.41 (m, IH), 5.55-5.62 (m, IH), 6.49 (dd) J = 8.6, 0.7 Hz, 1H), 6.84 (dd, J = 8.3, 0.8 Hz, 1 H, 7.43 (dd, J = 8.6, 2.3 Hz, 1 H), 7.55 (dd, J = 8.3, 2.3 Hz, 1 H), 8.05 (dd, J = 2.3, 0.7 Hz, 1 H) 8.11 (dd, J = 2.3, 0.8Hz, 1H)

· · · · · · · · · · · · · · · · · · · · · · · · · · ·

234 ·· ··

Table 140

Ig-5 mp 126-128 ° C; Δ NMR (CDCl 3) δ 1.75 (s, 6H), 1.78 (s, 6H), 2.07 (s, 6H), 2.55 (s, 6H), 3.90 (t, J = 6.0Hz, 4H), 4.53 (m, 2H), 5.37 (t, J = 6.6Hz, 2H), 6.47 (dd, J = 8.4, 0.9Hz, 2H), 7.17 (dd, J = 8.4, 2.4Hz, 2H), 7.82 (dd, J = 2.4) (0.9 Hz, 2H); IR (KBr): 3222, 1607, 1532, 1389, 1313, 981, 811 cm &lt; -1 &gt;. Ig-6 Ή NMR (300 MHz, CDCl 3) δ 1.75 (s, 6H), 1.78 (d, J = 0.9Hz, 6H), 2.10 (s, 6H), 3.36 (s, 6H), 3.91 (t, J = 0.9Hz) 4H), 4.53 (t, J = 5.0Hz, 2H), 5.34-5.42 (m, 2H), 6.48 (d, J = 8.5Hz, 2H), 7.42 (dd, J = 8.5, 2.3Hz, 2H) 8.05 (dd, J = 2.3, 0.8Hz, 2H) Ig-7 Δ NMR (300 MHz, CDCl 3) δ 1.80 (s, 3H), 1.83 (s, 3H), 2.08 (s, 3H), 2.12 (s, 3H), 3.34 (s, 3H), 3.39 (s, 3H) 4.89 (d, J = 6.9Hz, 2H), 5.17 (br s, 2H), 5.54-5.62 (m, 1 H), 6.84 (dd, J = 8.6, 0.8 Hz, 1 H), 7.53 (dd, J = 8.6 (2.3 Hz, 1 H), 8.09 (dd, J = 2.3, 0.8 Hz, 1 H), 8.32 (s, 2 H) Ig-8 Δ NMR (300 MHz, CDCl 3) δ 1.76 (s, 3H), 1.78 (s, 3H), 1.80 (s, 3H), 1.83 (s, 3H), 2.08 (s, 3H), 2.13 (s, 3H) 3.34 (s, 3H); 4.40 (s, J = 6.2Hz, 2H); 4.88 (d, J = 6.9Hz, 2H); 5.14-5.18 (m, 1H); 5.42 (m, 1H); 5.55-5.61 (m, 1H); 6.85 (dd, J = 8.5, 0.7 Hz, 1H); 7.54 (dd, J = 8.5,2.7 Hz, 1H); 2.7 (0.7 Hz, 1 H), 8.30 (s, 2 H) Ig-9 Δ NMR (300 MHz, CDCl 3) δ 1.79 (s, 3H), 1.83 (d, J = 0.9Hz, 3H), 2.07 (s, 3H), 2.08 (s, 3H), 3.34 (s, 3H), 3.40 (s, 3H), 4.67 (br s, 2H), 4.89 (d, J = 7.2Hz, 2H), 5.54-5.62 (m, IH), 6.84 (dd, J = 8.6, 0.7Hz, IH), 7.53 (dd, J = 8.6, 2.5 Hz, 1 H), 8.09 (dd, J = 2.5, 0.7 Hz, 1 H), 8.12 (d, J = 1.5 Hz, 1 H), 8.15 (d, J = 1.5 Hz, 1 H) Ig-10 Δ NMR (300 MHz, CDCl 3) δ 1.77 (s, 3H), 1.79 (s, 6H), 1.83 (s, 3H), 2.07 (s, 3H), 2.09 (s, 3H), 3.34 (s, 3H) 3.41 (s, 3H), 3.99 (t, J = 5.7Hz, 2H), 4.62 (brs, 1H), 4.88 (d, J = 6.9Hz, 2H), 5.34-5.42 (m, 1H), 5.55 -5.62 (m, 1 H), 6.84 (dd, J = 8.4, 0.8 Hz, 1H), 7.53 (dd, J = 8.4, 2.5 Hz, 1H), 8.02 (d, J = 1.5 Hz, 1H), 8.09 (dd, J = 2.5, 0.8 Hz, 1H)

• ··

• · · · · · · · · · · ·

235

Experiment 1: Suppressive effect on mitogenic activity of mouse splenocytes in vitro.

In a 96-well microtiter plate, 5x10® mouse C3H / HeN splenocytes were suspended in 0.1 ml RPMI 1640 medium containing 2 mM sodium bicarbonate, 50 units / ml penicillin, 50 µg / ml streptomycin and 5x10® M 2-mercaptoethanol and supplemented with 10 ml. % fetal bovine serum. Then, 5 µg / ml Concanavalin A (Con A) or 10 gg / ml lipopolysaccharide (LPS) as a mitogen was added to each well and at a predetermined concentration the compound of the invention so that the resulting volume in each well reached 0.2 ml. Each compound of the invention was dissolved in dimethylsulfoxide (DMSO) and diluted in the above RPMI 1640 medium to achieve a final concentration of 100 ng / ml or less. Splenocytes in a 96-well microtiter plate were cultured for 3 days at 37 ° C in an incubator maintaining 100% humidity, 5% CO 2 and 95% air. Then, 25 μΙ 6 mg / ml MTT [3- (4,5-dimethylthiazol-2-yl) -2,5-diphenyltetrazolium bromide] (Sigma) was added to each well and cultured for 4 hours at 37 ° C under the same conditions. After cultivation, 50 μΙ of 20% sodium dodecyl sulfate (SDS) containing 0.02 N hydrochloric acid was added to the formazan formed and the mixture was allowed to stand for 24 hours at 37 ° C to dissolve the formazan. The absorption rate (OD) of formazan produced relative to the number of viable cells was measured on an InterMed reading device equipped with a 570 nm filter (The Journal of Immunological Method, 65, 55-63, 1983). A 50% inhibitory concentration of cell proliferation (IC 50) was calculated from the correlation between the concentration of the compound of the invention and the intensity of absorption.

Experiment 2: Anti-proliferative activity of EL4 cells.

4x10 ⁴ / 0.1 ml mouse EL4 cells were suspended in a 96-well microtiter plate and 0.1 ml of the compound of the invention was added to the mixture at a concentration ranging from 0 to 5000 ng / ml . After a 3-day cultivation, the IC 50 was calculated by MTT as described in Experiment 1.

The results of Experiments 1 and 2 are shown in Table 141.

·· ···· · ·

236

Table 141

Compound C. ConA IC 50 (ng / ml) LPS IC 50 (ng / ml) EL-4 IC50 (ng / ml) Ia-2 ^ 10 <10 33 Ia-42 16 31 200 Ia-43 74 154 500 Ia-45 66 373 811 Ia-66 52 39 80 Ia-94 12 21 50 Ib-3 41 145 307 Ib-13 58 179 426 lb-16 3.1 6.7 400 Ib-17 29 60 78 Ib-20 51 196 576 Ib-23 78 283 651 Ib-37 92 361 114 Ib-40 16 55 60 Ib-44 60 317 426 Ib-54 <20 53 91 Ib-65 92 134 553 Ib-71 18 54 69 Ib-82 <20 <20 <20 Ib-101 42 261 493 Ic-1 48 158 473 Ic-14 15 Dec 53 207

As shown above, the compound of the present invention has immunosuppressive and antiallergic effects.

Experiment 3: Suppressive effect on ovalbumin (OVA) IgE production.

1) Animals

BALB / c mice (female, 8-10 weeks old) and Whistar rats (female, 8-10 weeks old), purchased from Japan SLC, Inc, were used. (Shizuoka).

2) Immunization methods ·· ·

237

BALB / c mice were immunized intraperitoneally with 0.2 ml of a suspension of 2 µg ovalbumin (OVA) and 2 mg aluminum hydroxide gel in saline. After 10 days, blood was collected from the heart, the sera separated and stored at -40 ° C until IgE antibody titer was measured.

3) Compounds

After the compound of the present invention was dissolved or suspended in Ν, Ν-dimethylacetamide, the mixture was diluted 20 times with neutral miglyol 812 oil. ). Administration was continued for 10 days from the day of immunization until the day before blood collection.

4) Measurement of anti-OVA IgE antibody titer (PCA titer)

The obtained mouse serum was diluted twice with saline and 50 µΙ of the solution was injected intradermally into the pre-cut areas on the backs of Whistar rats. After 24 hours, a passive cutaneous anaphylactic reaction (PCA) was induced by intravenous injection of 0.5 ml of saline containing 1 mg OVA and 5 mg Evans blue. After 30 minutes, the rats were sacrificed and a serum dilution that gave a bluish diameter greater than 5 mm was recorded as the PCA titer.

For example, when the serum is positive for the PCA response still at a dilution of ²⁷ , the anti-OVA IgE antibody titer of this mouse is defined as 7. The results are shown in Table 142.

·· ·

238

Table 142

Compound PCA titr Compound PCA titr Ia-356 5.3 Ib-281 0 Ib-37 0 Ib-283 3 Ib-69 1.5 Ib-284 6.8 Ib-90 1.7 Ib-285 2 Ib-218 5.5 Ib-293 5 Ib-219 <0 Ib-297 3 Ib-220 <0 Ib-298 2.3 Ib-221 0.3 Ib-299 0 Ib-222 <0 Ib-301 3 Ib-223 3.8 Ib-302 1.5 Ib-224 0 Ib-305 3 Ib-225 0 Ib-306 5.3 Ib-226 0 Ib-307 5 Ib-227 4.5 Ib-309 4.3 Ib-228 2.5 Ib-310 5.8 Ib-229 3 Ib-311 6.3 Ib-230 0 Ib-312 0 Ib-231 <0 Ib-322 4 Ib-232 1 Ib-329 3.8 Ib-233 2 Ib-330 0.5 Ib-234 <0 Ib-331 <0 Ib-235 <0 Ib-332 2.3 Ib-239 0 Ib-333 <0 Ib-240 0 Ib-334 <0 Ib-241 0 Ib-342 <0 Ib-242 1 Ib-343 0 Ib-243 2.3 Ib-344 0 Ib-244 0 Ib-350 2.3 Ib-245 5.3 Ib-351 2.8 Ib-246 0 Ib-352 <0 Ib-247 0 Ib-353 2.5 Ib-248 0 Ib-354 <0 Ib-249 0 Ib-358 <0 Ib-250 0 Ib-361 <0 Ib-259 0 Ib-396 <0 Ib-272 5.3 Ib-431 6.5 Ib-279 1 Ib-433 5.5 Ib-280 0 Ib-439 5.3 Ig-2 6.8

As shown above, the compound of the present invention has a suppressive effect on IgE production.

· Ti ti * * * * ti ti ti ti ti ti ti ti ti

239 »ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ti ** ** ** ** ** **

Medicinal product - example 1

Compound of the Invention (Ia-1) 15 mg

Starch 15 mg

Lactose 15 mg

Crystalline cellulose 19 mg

Polyvinyl alcohol 3 mg

Distilled water 30 ml

Calcium stearate 3 mg

After all of the above ingredients, except calcium stearate, were homogeneously mixed, the mixture was crushed and granulated, further dried to obtain a suitable granule size. After calcium stearate was added to the granules, tablets were formed by compression on a matrix.

Industrial applicability

As explained in the above examples, the compound of the present invention has significant immunosuppressive and antiallergic activity. The compound of the present invention is very useful as an immunosuppressive agent, an antiallergic agent and as an IgE suppressant.

Claims (53)

PATENTOVÉ Claims wherein ring A, ring B and ring C are each independently an optionally substituted aromatic carbon ring or an optionally substituted 5- or 6-membered heterocycle which may be fused to a benzene ring, W ¹ , W ² or W ³ represent a bond when ring A, ring B or ring C is an optionally substituted 5-membered heterocycle, X is -O-, -CH ² -, NR ¹ - wherein R ¹ is hydrogen, optionally substituted lower alkyl, lower alkenyl, lower alkylcarbonyl or optionally substituted lower alkoxycarbonyl or -S (O) _p - wherein p is an integer from 0 to 2 , Y is hydrogen, optionally substituted lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkynyl, optionally substituted acyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted lower alkoxycarbonyl, optionally substituted sulfamoyl, optionally substituted amino, optionally substituted aryl or optionally substituted five or six membered heterocycle, Y is optionally substituted lower alkoxy when X is -CH 2 -, Y is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl or optionally substituted arylsulfonyl when X is -O- or -NR ¹ -, one of V ¹ and V ² is a bond and the other is a bond, -Ο-, -NH-, -OCH ₂ -, -CH ₂ O-, -CH = CH-, C = C-, -CH (OR ² ) - wherein R ² is hydrogen or lower alkyl, -CO- or -NHCHR ³ - wherein R ³ is hydrogen or hydroxyl, and at least one of rings A, B and C is an optionally substituted aromatic carbon ring and at least one other is an optionally substituted five or six membered heterocycle that can fuse with the benzene ring when both V ¹ and V ² are single bonds, a salt or a hydrate thereof. 241 The compound of claim 1, wherein ring A is an optionally substituted benzene ring, salt or hydrate thereof. The compound of claim 1, wherein ring B is an optionally substituted benzene ring, an optionally substituted pyridine ring, an optionally substituted pyrimidine ring, an optionally substituted pyridazine ring, an optionally substituted pyrazine ring, an optionally substituted thiophene ring, an optionally substituted furan ring, an optionally substituted pyrazole ring or an optionally substituted oxazole ring, salt or hydrate thereof. The compound of claim 1, wherein ring C is an optionally substituted benzene ring, an optionally substituted pyridine ring, an optionally substituted pyrimidine ring, an optionally substituted pyridazine ring, an optionally substituted pyrazine ring, an optionally substituted isoxazole ring, an optionally substituted pyrazole ring, an optionally substituted benzothiazole ring , an optionally substituted morpholine ring, an optionally substituted piperazine ring, an optionally substituted imidazole ring, or an optionally substituted triazole ring, salt or hydrate thereof. The compound of claim 1, wherein X is -O- or -NR ¹ -, wherein R ¹ is hydrogen, methyl or prenyl, a salt thereof or a hydrate thereof. The compound of claim 1, wherein Y is hydrogen, optionally substituted lower alkyl, optionally substituted lower alkenyl, lower alkylsulfonyl, or optionally substituted acyl, a salt thereof, or a hydrate thereof. The compound of claim 1, wherein one of V ¹ and V ² is a single bond and the other is a single bond, -O- or -NH-, a salt thereof or a hydrate thereof. The compound of claim 1, wherein ring A is an optionally substituted benzene ring, ring B is an optionally substituted benzene ring, an optionally substituted pyridine ring, an optionally substituted pyrimidine ring, an optionally substituted pyridazine ring, an optionally substituted pyrazine ring, an optionally substituted ring. · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · ·· 242 thiophene ring, optionally substituted furan ring, optionally substituted pyrazole ring or optionally substituted oxazole ring, ring C is optionally substituted benzene ring, optionally substituted pyridine ring, optionally substituted pyrimidine ring, optionally substituted pyridazine ring, optionally substituted pyrazine ring, optionally substituted isoxazole a ring, an optionally substituted pyrazole ring, an optionally substituted benzothiazole ring, an optionally substituted morpholine ring, an optionally substituted piperazine ring, an optionally substituted imidazole ring, or an optionally substituted triazole ring, X is -O- or -NR ¹ -, wherein R ¹ is hydrogen, methyl or prenyl, Y is an optionally substituted lower alkyl or an optionally substituted lower alkenyl and one of V ¹ and V ² is a single bond and the other is a single bond, -O- or -NH-, a salt thereof or a hydrate thereof. A compound according to any one of claims 1 to 8, wherein 2 of rings A, B and C are optionally substituted benzene rings and the remaining is an optionally substituted 5- or 6-membered heterocycle which may be fused to a benzene ring, a salt thereof or a hydrate thereof. A pharmaceutical composition for use as an immunosuppressor comprising a compound according to any one of claims 1 to 9, a salt thereof or a hydrate thereof. Pharmaceutical composition used as an antiallergic agent, comprising a compound according to any one of claims 1 to 9, a salt thereof or a hydrate thereof. A pharmaceutical composition for use as an IgE suppressor comprising a compound according to any one of claims 1 to 9, a salt thereof or a hydrate thereof. · · · · · · · · · · · · · · · · · · · · · · 243 Use of a compound according to any one of claims 1 to 9, a salt thereof or a hydrate thereof, for the manufacture of a medicament for suppressing the immune response, treating or preventing allergic diseases. 14. Compound of formula (1b '): wherein ring C is an optionally substituted 5- or 6-membered heterocycle that can be fused to a benzene ring, W ⁸ represents a bond when ring C is a 5-membered heterocycle, X and X 'are each independently -O-, -CH ₂ -, -NR ¹ - (wherein R ¹ is hydrogen, optionally substituted lower alkyl, lower alkenyl, lower alkylcarbonyl, or optionally substituted lower alkoxycarbonyl) or -S (O ) p- where p is an integer from 0 to 2, Y and Y 'are each independently optionally substituted lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkynyl, optionally substituted acyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted lower alkoxycarbonyl, optionally substituted amino, optionally substituted sulfamoyl, optionally substituted aryl or optionally substituted 5 or 6 membered heterocycle, R 1 together with Y and Y 'form - (CH ₂ ) m -, - (CH ₂ ) ₂ -Q- (CH ₂ ) ₂ - (where Q is CH ₂ , O, Sor NR), -CR '= CH-CH = CR'-, -CH = N-CH = CH-, -N = CH-N = CH-, -C (= 0) O _(CH2) n-, -C (= O) -NR '- (CH ₂ ) N- or -C (= O) -NR'-N = CH- wherein m is 4 or 5, n is 2 or 3, R' is hydrogen, lower alkyl or lower alkenyl, Y is optionally substituted lower alkoxy when X is -CH ₂ -, Y 'is optionally substituted lower alkoxy when X' is -CH ₂ -, Y is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkoxysulfonyl, or optionally substituted arylsulfonyl when X is -O- or -NR ¹ -, Y 'is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkoxysulfonyl or optionally substituted arylsulfonyl when X' is -O- or -NR ¹ -, 244 • · · · ··· ··· Y is hydrogen or halogen when X is -CH ² - or -NR ¹ -, Y 'is hydrogen or halogen when X' is -CH ² - or -NR ¹ -. R ⁴ , R ®, R ®, R ⁷ , R ®, R ⁹ , R ¹⁰ and R ¹¹ are independently hydrogen, halogen, hydroxyl, optionally substituted lower alkyl, optionally substituted lower alkoxy, optionally substituted lower alkenyl, optionally substituted lower alkenyloxy, optionally substituted cycloalkyloxy, optionally substituted acyloxy, carboxyl, optionally substituted lower alkoxycarbonyl, optionally substituted lower alkenyloxycarbonyl, optionally substituted lower alkylthionyl, optionally substituted lower alkenylthionyl, optionally substituted amino, optionally substituted carbamoyl, guanidino, guanidino, guanidino, guanidino , optionally substituted lower alkylsulfonyloxy, optionally substituted arylsulfonyl, or optionally substituted arylsulfonyloxy, with the exception of compounds wherein all R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ are hydrogen and halogen, a salt thereof or a hydrate thereof. A compound according to claim 14, wherein R ⁴ and R ⁵ are independently hydrogen, halogen or lower alkoxy, a salt thereof or a hydrate thereof. The compound of claim 14, wherein one of R ⁴ and R ⁶ is hydrogen and the other is halogen, a salt thereof or a hydrate thereof. A compound according to any one of claims 14 to 16, wherein both R ® and R ⁷ are hydrogen, a salt thereof or a hydrate thereof. The compound of claim 14, wherein R ⁸ and R ¹¹ are independently of each other optionally substituted lower alkyl or optionally substituted lower alkoxy, a salt thereof or a hydrate thereof. A compound according to claim 14, wherein R ® and R ¹¹ are independently methyl or methoxy, a salt thereof or a hydrate thereof 245 A compound according to any one of claims 14, 18 and 19, wherein R ⁹ and R ¹⁹ are independently hydrogen or optionally substituted lower alkyl, a salt thereof or a hydrate thereof. The compound of claim 14, wherein both R ® and R ¹¹ are optionally substituted lower alkyl or both R ® and R ¹¹ are optionally substituted lower alkoxy and both R ⁹ and R ¹⁹ are simultaneously hydrogen or both R ⁹ and R ¹⁹ are optionally substituted lower alkyl, salt or hydrate thereof. A compound according to any one of claims 14, 16 and 21, wherein ring C is a 5- or 6-membered heterocycle containing at least one nitrogen atom, a salt thereof or a hydrate thereof. A compound according to any one of claims 14, 16 and 21, wherein ring C is a six membered heterocycle containing at least one nitrogen atom, a salt thereof or a hydrate thereof. A compound according to any one of claims 14, 16 and 21, wherein ring C is an optionally substituted pyridine or an optionally substituted pyrimidine, a salt thereof or a hydrate thereof. 25. Compound of formula (Ia '): wherein ring B is an optionally substituted five or six membered ring containing one or two heteroatoms (wherein the substituent is halogen, hydroxyl, optionally substituted lower alkyl, optionally substituted lower alkoxy, optionally substituted lower alkenyl, optionally substituted lower alkenyloxy, optionally substituted acyloxy, carboxyl , optionally substituted lower alkoxycarbonyl, optionally substituted lower alkenyloxycarbonyl, optionally substituted alkylthionyl, optionally substituted lower alkenylthionyl, optionally substituted amino, guanidine, nitro, optionally substituted lower 246 alkylsulfonyl, optionally substituted lower alkylsulfonyloxy, optionally substituted arylsulfonyl or optionally substituted arylsulfonyloxy, except the compound wherein ring B is substituted only by halogen (halogens), and W ² represents a bond when ring B is a five membered heterocycle, X, X ', Y and Y' are the same substituents as defined in claim 14, R 1 together with Y or Y 'form - (CH 2) m -, - (CH 2) 2 -Q- (CH 2) 2 - (wherein Q is CH 2, O, S or NR), -CR' = CH-CH = CR- CH = N-CH = CH-, -N = CH-N = CH-, -C (= O) O (CH ₂ ) n -, -C (= O) -NR '- (CH ₂ ) N- or -C (= O) -NR'-N = CH-, wherein m is 4 or 5, n is 2 or 3 and R 'is hydrogen, lower alkyl or lower alkenyl, Y is optionally substituted lower alkoxy when X is -CH 2 -, Y 'is optionally substituted lower alkoxy when X' is -CH 2 -, Y is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl or optionally substituted arylsulfonyl when X is -O- or -NR ¹ -, Y 'is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl, or optionally substituted arylsulfonyl when X' is - O- or -NR ¹ -, Y is hydrogen or halogen when X is -CH ₂ - or -NR ¹ -, Y 'is hydrogen or halogen when X' is -CH ² - or -NR ¹ -, R ⁴ , R ⁸ , R ⁸ , R ⁷ , R ¹² , R ¹³ , R ¹⁴ and R ¹⁸ are independently hydrogen, halogen, hydroxyl, optionally substituted lower alkyl, optionally substituted lower alkoxy, optionally substituted lower alkenyl, optionally substituted lower alkenyloxy, optionally substituted acyloxy, carboxyl, optionally substituted lower alkoxycarbonyl, optionally substituted lower alkenyloxycarbonyl, optionally substituted alkylthionyl, optionally substituted lower alkenylthionyl, optionally substituted amino, optionally substituted carbamoyl, guanidino, lower alkyl, optionally substituted, optionally substituted, , optionally substituted arylsulfonyl or optionally substituted arylsulfonyloxy, except (i) a compound wherein Y and Y 'are simultaneously hydrogen, (ii) compounds wherein at least one of Y and Y' is optionally substituted acyl, ·· · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · (Iii) compounds wherein at least one of -XY and -XY 'is unsubstituted lower alkoxy, (iii) compounds wherein -XY and -X'-Y' are simultaneously optionally substituted lower alkoxy or amino substituted by phenyl, a salt thereof or hydrate. The compound of claim 25, wherein R ⁴ and R ⁸ are independently hydrogen, halogen or lower alkyl, a salt thereof or a hydrate thereof. The compound of claim 25, wherein one of R ⁴ and R ⁸ is hydrogen and the other is halogen, a salt thereof or a hydrate thereof. A compound according to any one of claims 25 to 27, wherein both R ® and R ⁷ are hydrogen, a salt thereof or a hydrate thereof. A compound according to claim 25 or 27, wherein ring B is a 5- or 6-membered heterocycle containing at least one nitrogen atom, a salt thereof or a hydrate thereof. The compound of claim 25 or 27, wherein ring B is a six-membered heterocycle containing at least one nitrogen atom, salt or hydrate thereof. A compound according to claim 25 or 27, wherein ring B is optionally substituted pyridine or optionally substituted pyrimidine, a salt thereof or a hydrate thereof. A compound according to claim 25 or 27, wherein R ¹² , R ¹³ , R ¹⁴ and R ¹⁸ are independently hydrogen, halogen or lower alkyl, a salt thereof or a hydrate thereof. The compound of claim 14 or 25, wherein one of X and X 'is -O- and the other is -NR ¹ , wherein R ¹ is hydrogen, optionally substituted lower alkyl, lower alkenyl, lower alkylcarbonyl, or optionally substituted lower alkoxycarbonyl, a salt thereof or a hydrate. φ φ · φ φ · φ · · · · · 248 A compound according to claims 14 or 25 wherein one of X and X 'is -O- and the other is -NR ¹ wherein R ¹ is hydrogen, lower alkyl or lower alkenyl and Y and Y' are independently optionally substituted lower alkyl or an optionally substituted lower alkenyl, salt or hydrate thereof. A compound according to claims 33 or 34, wherein R ¹ is hydrogen, a salt thereof or a hydrate thereof. The compound of claims 14 or 25, wherein one of-X-Y and -X'-Y 'is an optionally substituted lower alkylamine or an optionally substituted lower alkenylamine and the other is an optionally substituted lower alkoxy or an optionally substituted lower alkenyloxy, a salt thereof or a hydrate thereof. The compound of claims 14 or 25, wherein one of -X-Y and -X'-Y 'is an optionally substituted lower alkylamine or an optionally substituted lower alkenylamine and the other is prenoxyl, a salt thereof or a hydrate thereof. A compound according to claim 14, wherein R ⁴ , R ⁵ , R ® and R ⁷ are independently hydrogen, halogen or lower alkyl, wherein R ® and R ¹¹ are independently hydrogen, halogen, optionally substituted lower alkyl, optionally substituted lower alkoxy or lower alkoxycarbonyl wherein R ⁹ and R ¹⁰ are independently hydrogen, optionally substituted lower alkyl or optionally substituted lower alkoxy, one of X and X 'is -O- and the other is -NR ¹ -, wherein R ¹ is hydrogen, lower alkyl or lower alkenyl or lower alkylcarbonyl, Y and Y 'are independently optionally substituted lower alkyl, optionally substituted lower alkenyl or optionally substituted lower alkynyl, and ring C is optionally substituted pyridine or optionally substituted pyrimidine, its salt or hydrate . The compound of claim 14, wherein X 1 is -O-, -NR ¹ -, or -S (O) p - and Ring C is an optionally substituted 5-membered heterocycle containing one or two heteroatoms, salt or hydrate thereof. ΦΦ 99 ♦ 9 · Φ φ Φ ·· 249 φ φ ···· φ · · ΦΦ 99 40. The compound of claim 25, wherein R ^4, R ^5, R ⁶ and R ⁷ are independently hydrogen, halogen or lower alkyl, R ^12, R ^13, R ¹⁴ and R ¹ ® are independently hydrogen, halogen or lower alkyl, ring B is optionally substituted pyridine or optionally substituted pyrimidine, wherein the substituent is optionally substituted lower alkyl or optionally substituted lower alkoxy, one of X and X 'is -O- and the other is -NR ¹ -, wherein R ¹ is hydrogen , lower alkyl, lower alkenyl or lower alkylcarbonyl, and Y and Y 'are independently optionally substituted lower alkyl, optionally substituted lower alkenyl or optionally substituted lower alkynyl, a salt thereof or a hydrate thereof. 41. Compound of general formula If ': wherein one of rings B and C is an optionally substituted five or six membered heterocycle containing one or two heteroatoms and the other is a six membered heterocycle containing at least one nitrogen atom, with the exception of a compound wherein each substituent of ring B is cyano or halogen, X, X ', Y, Y' and W ³ are the same as defined in claim 14, W ² is the same as defined in claim 25, R 1 together with Y and Y 'form - (CH ₂ ) m -, - (CH ₂ ) ₂ -Q- (CH ₂ ) ₂ - (wherein Q is CH ₂ , O, S or NR'), -CR '= CH-CH = CR'-, -CH = N-CH = CH-, -N = CH-N = CH-, -C (= O) -O (CH ₂ ) n -, C (= O) -NR - _(CH2) n- or -C (= O) -NR'-N = CH- wherein m is 4 or 5, n is 2 or 3, R 'is hydrogen, lower alkyl or lower alkenyl, Y is optionally substituted lower alkoxy when X is -CH ₂ -, Y 'is optionally substituted lower alkoxy when X' is -CH ₂ -, Y is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl, or optionally substituted arylsulfonyl when X is -O- or -NR ¹ -, 250 Y 'is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl, or optionally substituted arylsulfonyl when X' is -O- or -NR ¹ -, Y is hydrogen or halogen when X is -CH ² - or -NR ¹ -, Y 'is hydrogen or halogen when X' is -CH ² - or -NR ¹ -, R ⁴ , R ⁵ , R ® and R ⁷ are the same as defined in claim 14, a salt thereof or a hydrate thereof. 42. A compound having the general formula lg ': wherein rings A and C are independently an optionally substituted five or six membered heterocycle containing one or two heteroatoms, W ¹ is a bond when ring A is a five membered heterocycle, X, X ', Y, Y' and W ¹ are the same as defined in claim 14, R 1 together with Y or Y 'form - (CH 2) m -, - (CH 2) 2 -Q- (CH 2) 2 - (wherein Q is CH 2, O, S or NR), -CR' = CH-CH = CR ' -, -CH = N-CH = CH-, -N = CH-N = CH-, -C (= O) O (CH ₂ ) n -, -C (= O) -NR '- (CH ₂ ) N- or -C (= O) -NR'-N = CH-, wherein m is 4 or 5, n is 2 or 3, R 'is hydrogen, lower alkyl or lower alkenyl, Y is optionally substituted lower alkoxy when X is -CH 2 -, Y 'is optionally substituted lower alkoxy when X' is -CH 2 -, Y is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl or optionally substituted arylsulfonyl when X is -O- or -NR ¹ -, Y 'is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl or optionally substituted arylsulfonyl when X' is - O- or -NR ¹ -, Y is hydrogen or halogen when X is -CH ² - or -NR ¹ -, Y 'is hydrogen or halogen when X' is -CH ² - or -NR ¹ -, 251 R,, R ⁹ , R ¹⁹ and R ¹¹ are the same as defined in claim 14, except the compound wherein all R,, R ⁹ , R ¹⁹ and R ¹¹ are hydrogen and halogen, a salt thereof or a hydrate thereof. 43. A pharmaceutical composition for use as an immunosuppressant comprising a compound of formula (1b '). wherein ring C and W ® are the same as defined in claim 14, X and X 'are independently -O-, -CH ² -, -NR ¹ -, (wherein R ¹ is hydrogen, optionally substituted lower alkyl, lower alkenyl, lower alkylcarbonyl, or optionally substituted lower alkoxycarbonyl), -S (O) p- (where p is an integer between 0 and 2) or a single bond, Y and Y 'are as defined in claim 14, R 1 together with Y or Y 'form - (CH 2) m -, - (CH 2) 2 -Q- (CH 2) 2 - (wherein Q is CH 2, O, or NR'), -CR '= CH-CH = CR '-, -CH = N-CH = CH-, -N = CH-N = CH-, -C (= O) O (CH ₂ ) n -, -C (= O) -NR' - (CH ₂₎ ) N- or -C (= O) -NR'-N = CH-, wherein m is 4 or 5, n is 2 or 3, R 'is hydrogen, lower alkyl or lower alkenyl, Y is lower optionally substituted lower alkoxy when X is -CH 2 -, Y 'is lower optionally substituted lower alkoxy when X' is -CH 2 -, Y is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl, or optionally substituted arylsulfonyl when X is -O- or -NR ¹ -, Y 'is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl, or optionally substituted arylsulfonyl when X' is -O- or -NR ¹ -, Y is hydrogen or halogen when X is -CH ² - or -NR ¹ -, Y 'is hydrogen or halogen when X' is -CH ² - or -NR ¹ -, fc 9c · fcfc · fcfc · fcfcfcfc fcfc fcfc · ·· ·· fcfc · • fcfcfcfc fcfcfcfc • fcfcfcfc fcfc fc fcfc ·· 252 Y 'is hydrogen, hydroxyl, halogen, nitro or oxo when X' is a single bond, R ⁴ , R ®, R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ are the same as defined in claim 14, except for a compound wherein all R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ are hydrogen and halogen, a salt thereof or a hydrate thereof. 44. A pharmaceutical composition useful as an immunosuppressor comprising a compound of Formula Ia ': wherein ring B is an optionally substituted 5- or 6-membered heterocycle containing one or two heteroatoms, with the exception of a compound wherein each substituent of ring B is cyano and halogen, W ² represents a bond when ring B is a five membered heterocycle, X, X ', Y and Y' are the same as defined in claim 14, R 1 together with Y or Y 'form - (CH 2) m -, - (CH 2) 2 -Q- (CH 2) 2 - (wherein Q is CH 2, O, Or NR), -CR '= CH-CH = CR'-, -CH = N-CH = CH-, -N = CH-N = CH-, -C (= O) O (CH ₂ ) n -, -C (= O) -NR '- (CH ₂ ) N- or -C (= O) -NR'-N = CH-, wherein m is 4 or 5, n is 2 or 3 and R 'is hydrogen, lower alkyl or lower alkenyl, Y is optionally substituted lower alkoxy when X is -CH 2 -, Y 'is optionally substituted lower alkoxy when X' is -CH 2 -, Y is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl or optionally substituted arylsulfonyl when X is -O- or -NR ¹ -, Y 'is optionally substituted lower alkoxycarbonyl, optionally substituted lower alkylsulfonyl, or optionally substituted arylsulfonyl when X' is - O- or -NR ¹ -, Y is hydrogen or halogen when X is -CH ² - or -NR ¹ -, Y 'is hydrogen or halogen when X' is -CH ² - or -NR ¹ -, R ⁴ , R ®, R ⁸ , R ⁷ , R ¹² , R ¹ ®, R ¹⁴ and R ¹ ® are the same as defined in claim 25, 253 except (i) a compound wherein -XY and -XY 'are simultaneously unsubstituted lower alkyl, optionally substituted lower alkoxy or unsubstituted acyloxy, (ii) compounds wherein one of -XY and -X'-Y' is methyl and the other is methoxy, and (iii) compounds wherein -X'-Y 'is hydrogen or halogen and -XY is unsubstituted lower alkyl, unsubstituted lower alkoxy or lower dialkylamine, a salt thereof or a hydrate thereof 45. A pharmaceutical composition for use as an immunosuppressor comprising a compound of the formula If ' 41, a salt thereof or a hydrate thereof. 46. A pharmaceutical composition for use as an immunosuppressant comprising a compound of the general formula Ig ' according to claim 42, a salt thereof or a hydrate thereof. A pharmaceutical composition for use as an antiallergic agent comprising a compound of formula If 'according to claim 41, a compound of formula Ig' according to claim 42, a compound of formula 1b 'according to claim 43, a compound of formula Ia 'according to claim 44, a salt thereof or a hydrate thereof. 48. A pharmaceutical composition for use as an IgE suppressor comprising a compound of formula If ' according to claim 41, a compound of formula Ig ' according to claim 42, a compound of formula Ib ' , a compound of formula Ia 'according to claim 44, a salt thereof or a hydrate thereof. Use of a compound of formula If 'according to claim 41, a compound of formula Ig' according to claim 42, a compound of formula 1b 'according to claim 43, a compound of formula 1a' according to claim 44, salts thereof or hydrate, for the manufacture of a medicament for suppressing the immune response, treating or preventing allergic diseases. 254 ·· »· A method of suppressing an immune response comprising administering a compound of formula If 'according to claim 41, a compound of formula Ig' according to claim 42, a compound of formula 1b 'according to claim 43, a compound of the formula or a salt or hydrate thereof. A method of treating or preventing allergic diseases, comprising administering a compound of formula If 'according to claim 41, a compound of formula Ig' according to claim 42, a compound of formula 1b 'according to claim 43, compounds with the formula la 'according to claim 44, a salt thereof or a hydrate thereof. 254 ftftftft ftftftft ftft ftft ftft ftft ftft ftft ftft ftft ft ft ftft .alpha 52. A compound of the formula wherein R4 and R5 are independently hydrogen, halogen or lower alkoxy, R6 and R7 independently of each other hydrogen, halogen or lower alkyl, both R8 and R11 are lower alkyl or one of R8 and R11 is lower alkyl and the other is lower alkoxy, both R 9 and R 10 are hydrogen or both R 9 and R 10 are lower alkyl, one of XY and -XY 'is an optionally substituted lower alkylamine or an optionally substituted lower alkenylamine and the other is prenoxyl, a salt thereof or a hydrate thereof. 53. A compound of the general formula X'-Y 'is the same as defined in claim 14, a salt thereof or a hydrate thereof.