JP4312829B2 - 置換(スルフィン酸、スルホン酸、またはスルホニルアミノもしくはスルフィニルアミノ)n−[(アミノイミノメチル)フェニルアルキル]−アザ複素環アミド化合物 - Google Patents
置換(スルフィン酸、スルホン酸、またはスルホニルアミノもしくはスルフィニルアミノ)n−[(アミノイミノメチル)フェニルアルキル]−アザ複素環アミド化合物 Download PDFInfo
- Publication number
- JP4312829B2 JP4312829B2 JP50202997A JP50202997A JP4312829B2 JP 4312829 B2 JP4312829 B2 JP 4312829B2 JP 50202997 A JP50202997 A JP 50202997A JP 50202997 A JP50202997 A JP 50202997A JP 4312829 B2 JP4312829 B2 JP 4312829B2
- Authority
- JP
- Japan
- Prior art keywords
- substitution
- oxopyrrolidin
- hydrogen
- trifluoroacetate
- sulfonic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- -1 sulfinylamino Chemical group 0.000 title claims description 476
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 title 1
- 125000003884 phenylalkyl group Chemical group 0.000 title 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 title 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 607
- 229910052739 hydrogen Inorganic materials 0.000 claims description 292
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 245
- 229910052757 nitrogen Inorganic materials 0.000 claims description 183
- 239000001257 hydrogen Substances 0.000 claims description 118
- 125000000217 alkyl group Chemical group 0.000 claims description 100
- CKARHIGQRRNVFD-UHFFFAOYSA-N 7-methoxynaphthalene-2-sulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=CC2=CC(OC)=CC=C21 CKARHIGQRRNVFD-UHFFFAOYSA-N 0.000 claims description 82
- 150000002431 hydrogen Chemical group 0.000 claims description 79
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 76
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 64
- 150000003839 salts Chemical class 0.000 claims description 52
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 49
- 125000001072 heteroaryl group Chemical group 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 37
- 230000015572 biosynthetic process Effects 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 25
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- SEDIJOBQZYCMRX-UHFFFAOYSA-N 4,5-dichlorothiophene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC(Cl)=C(Cl)S1 SEDIJOBQZYCMRX-UHFFFAOYSA-N 0.000 claims description 11
- XCJLXFIGEMUOEE-UHFFFAOYSA-N acetamide;2,2,2-trifluoroacetic acid Chemical compound CC(N)=O.OC(=O)C(F)(F)F XCJLXFIGEMUOEE-UHFFFAOYSA-N 0.000 claims description 9
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
- 150000001204 N-oxides Chemical class 0.000 claims description 7
- 208000007536 Thrombosis Diseases 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 230000002792 vascular Effects 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000003146 anticoagulant agent Substances 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- 238000002560 therapeutic procedure Methods 0.000 claims description 6
- IIGVTBXGSGACRA-UHFFFAOYSA-N 4-(3-methoxyphenyl)benzenesulfonic acid Chemical compound COC1=CC=CC(C=2C=CC(=CC=2)S(O)(=O)=O)=C1 IIGVTBXGSGACRA-UHFFFAOYSA-N 0.000 claims description 5
- ADAKMYBJTQFVMB-UHFFFAOYSA-N 4-(3-methylphenyl)benzenesulfonic acid Chemical compound CC1=CC=CC(C=2C=CC(=CC=2)S(O)(=O)=O)=C1 ADAKMYBJTQFVMB-UHFFFAOYSA-N 0.000 claims description 5
- GXWGRQOMOLFZDN-UHFFFAOYSA-N 5-chloro-3-methyl-1-benzothiophene-2-sulfonic acid Chemical compound C1=C(Cl)C=C2C(C)=C(S(O)(=O)=O)SC2=C1 GXWGRQOMOLFZDN-UHFFFAOYSA-N 0.000 claims description 5
- QWZZUZAIHNZLEN-UHFFFAOYSA-N 5-pyridin-2-ylthiophene-2-sulfonic acid Chemical compound S1C(S(=O)(=O)O)=CC=C1C1=CC=CC=N1 QWZZUZAIHNZLEN-UHFFFAOYSA-N 0.000 claims description 5
- OKAUOXITMZTUOJ-UHFFFAOYSA-N 7-aminonaphthalene-2-sulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 OKAUOXITMZTUOJ-UHFFFAOYSA-N 0.000 claims description 5
- WIOKCKSFXZUPKG-LTCKWSDVSA-N CN[C@@H](CCN1CC2=CC(C=NN)=CC=C2)C1=O.COC1=CC=C(C=CC(S(O)(=O)=O)=C2)C2=C1.OC(C(F)(F)F)=O Chemical compound CN[C@@H](CCN1CC2=CC(C=NN)=CC=C2)C1=O.COC1=CC=C(C=CC(S(O)(=O)=O)=C2)C2=C1.OC(C(F)(F)F)=O WIOKCKSFXZUPKG-LTCKWSDVSA-N 0.000 claims description 5
- 125000001475 halogen functional group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- XGVKSGFXYYTXDJ-YNMZEGNTSA-N 2-[[(3S)-1-[(3-methanehydrazonoylphenyl)methyl]-2-oxopyrrolidin-3-yl]-(7-methoxynaphthalen-2-yl)sulfonylamino]-N-(2-phenylethyl)acetamide 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.NN=CC=1C=C(CN2C([C@H](CC2)N(CC(=O)NCCC2=CC=CC=C2)S(=O)(=O)C2=CC3=CC(=CC=C3C=C2)OC)=O)C=CC1 XGVKSGFXYYTXDJ-YNMZEGNTSA-N 0.000 claims description 4
- MRQFYDABMZCZLM-CZCBIWLKSA-N FC(C(=O)O)(F)F.NN=CC=1C=C(CN2C([C@H](CC2)N(CC(=O)NCC2=CC=CC=C2)S(=O)(=O)C2=CC3=CC(=CC=C3C=C2)OC)=O)C=CC1 Chemical compound FC(C(=O)O)(F)F.NN=CC=1C=C(CN2C([C@H](CC2)N(CC(=O)NCC2=CC=CC=C2)S(=O)(=O)C2=CC3=CC(=CC=C3C=C2)OC)=O)C=CC1 MRQFYDABMZCZLM-CZCBIWLKSA-N 0.000 claims description 4
- UMQQZKPPZYVKBT-BDQAORGHSA-N N-[(3S)-1-[(3-methanehydrazonoylphenyl)methyl]-2-oxopyrrolidin-3-yl]quinoline-6-sulfonamide 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NN=CC1=CC=CC(CN2C([C@@H](NS(=O)(=O)C=3C=C4C=CC=NC4=CC=3)CC2)=O)=C1 UMQQZKPPZYVKBT-BDQAORGHSA-N 0.000 claims description 4
- ASVYULXOOYAQPJ-FYZYNONXSA-N 4-amino-3-[[(3s)-3-[(4-tert-butylphenyl)sulfonylamino]-2-oxopyrrolidin-1-yl]methyl]benzenecarboximidamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)N[C@@H]1C(=O)N(CC=2C(=CC=C(C=2)C(N)=N)N)CC1 ASVYULXOOYAQPJ-FYZYNONXSA-N 0.000 claims description 3
- UVMRQBRTXBKDCT-FGJQBABTSA-N 4-amino-3-[[(3s)-3-[(7-methoxynaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]methyl]benzenecarboximidamide;dihydrochloride Chemical compound Cl.Cl.C([C@@H](C1=O)NS(=O)(=O)C=2C=CC3=CC=C(C=C3C=2)OC)CN1CC1=CC(C(N)=N)=CC=C1N UVMRQBRTXBKDCT-FGJQBABTSA-N 0.000 claims description 3
- 230000001154 acute effect Effects 0.000 claims description 3
- 206010000891 acute myocardial infarction Diseases 0.000 claims description 3
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 3
- 210000001367 artery Anatomy 0.000 claims description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
- 208000009190 disseminated intravascular coagulation Diseases 0.000 claims description 3
- YFVJOHQIZCJFGM-UHFFFAOYSA-N methyl 2-[4-methanehydrazonoyl-2-[[3-[(7-methoxynaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]methyl]phenoxy]acetate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC(=O)COC1=CC=C(C=NN)C=C1CN1C(=O)C(NS(=O)(=O)C=2C=C3C=C(OC)C=CC3=CC=2)CC1 YFVJOHQIZCJFGM-UHFFFAOYSA-N 0.000 claims description 3
- 230000001575 pathological effect Effects 0.000 claims description 3
- 230000002093 peripheral effect Effects 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 3
- 210000005166 vasculature Anatomy 0.000 claims description 3
- KYEUOIMTDTWVJE-FTBISJDPSA-N 4-amino-3-[[(3s)-3-[(7-methoxynaphthalen-2-yl)sulfonylmethylamino]-2-oxopyrrolidin-1-yl]methyl]benzenecarboximidamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C([C@@H](C1=O)NCS(=O)(=O)C=2C=CC3=CC=C(C=C3C=2)OC)CN1CC1=CC(C(N)=N)=CC=C1N KYEUOIMTDTWVJE-FTBISJDPSA-N 0.000 claims description 2
- 206010002388 Angina unstable Diseases 0.000 claims description 2
- 208000005189 Embolism Diseases 0.000 claims description 2
- 206010022562 Intermittent claudication Diseases 0.000 claims description 2
- 208000032382 Ischaemic stroke Diseases 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 206010040070 Septic Shock Diseases 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims description 2
- 208000001435 Thromboembolism Diseases 0.000 claims description 2
- 208000007814 Unstable Angina Diseases 0.000 claims description 2
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- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
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- 238000006467 substitution reaction Methods 0.000 claims 142
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 238000007887 coronary angioplasty Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
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- 239000004615 ingredient Substances 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 438
- 238000005160 1H NMR spectroscopy Methods 0.000 description 288
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 287
- 239000000243 solution Substances 0.000 description 243
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 224
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- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 29
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- 238000000034 method Methods 0.000 description 21
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- CCRMAATUKBYMPA-UHFFFAOYSA-N trimethyltin Chemical compound C[Sn](C)C.C[Sn](C)C CCRMAATUKBYMPA-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/085—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a nitrogen atom directly attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/416—2,5-Pyrrolidine-diones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/12—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/481,024 | 1995-06-07 | ||
| US08/481,024 US5612353A (en) | 1995-06-07 | 1995-06-07 | Substituted (sulfinic acid, sulfonic acid, sulfonylamino or sulfinylamino) N-[(aminoiminomethyl)phenylalkyl]-azaheterocyclylamide compounds |
| PCT/US1996/009816 WO1996040679A1 (en) | 1995-06-07 | 1996-06-07 | Substituted (sulfinic acid, sulfonic acid, sulfonylamino or sulfinylamino) n-[(aminoiminomethyl)phenylalkyl]-azaheterocyclylamide compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH11507368A JPH11507368A (ja) | 1999-06-29 |
| JPH11507368A5 JPH11507368A5 (enExample) | 2004-07-29 |
| JP4312829B2 true JP4312829B2 (ja) | 2009-08-12 |
Family
ID=23910281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50202997A Expired - Fee Related JP4312829B2 (ja) | 1995-06-07 | 1996-06-07 | 置換(スルフィン酸、スルホン酸、またはスルホニルアミノもしくはスルフィニルアミノ)n−[(アミノイミノメチル)フェニルアルキル]−アザ複素環アミド化合物 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5612353A (enExample) |
| EP (1) | EP0853618B1 (enExample) |
| JP (1) | JP4312829B2 (enExample) |
| KR (1) | KR100291711B1 (enExample) |
| CN (1) | CN1190395A (enExample) |
| AP (1) | AP799A (enExample) |
| AT (1) | ATE520655T1 (enExample) |
| AU (1) | AU714319B2 (enExample) |
| BG (1) | BG63628B1 (enExample) |
| BR (1) | BR9608405A (enExample) |
| CA (1) | CA2223403C (enExample) |
| CZ (1) | CZ385397A3 (enExample) |
| EA (1) | EA000700B1 (enExample) |
| HU (1) | HUP9801882A3 (enExample) |
| MX (1) | MX9709977A (enExample) |
| NO (1) | NO310457B1 (enExample) |
| OA (1) | OA10752A (enExample) |
| PL (1) | PL323780A1 (enExample) |
| SI (1) | SI9620093A (enExample) |
| SK (1) | SK160697A3 (enExample) |
| WO (1) | WO1996040679A1 (enExample) |
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| US6034093A (en) * | 1995-06-07 | 2000-03-07 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Substituted sulfonic acid N-[(aminoiminomethyl)phenylalkyl]-azaheterocyclylamide compounds |
| US5958918A (en) * | 1995-06-07 | 1999-09-28 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Substituted (sulfinic acid, sulfonic acid, sulfonylamino or sulfinylamino) N- (aminominomethyl)phenylalkyl!-azaheterocyclylamide compounds |
| US5731315A (en) * | 1995-06-07 | 1998-03-24 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Substituted sulfonic acid n- (aminoiminomethyl)phenylalkyl!-azaheterocyclamide compounds |
| US6080767A (en) * | 1996-01-02 | 2000-06-27 | Aventis Pharmaceuticals Products Inc. | Substituted n-[(aminoiminomethyl or aminomethyl)phenyl]propyl amides |
| US6057342A (en) * | 1996-08-16 | 2000-05-02 | Dupont Pharmaceutical Co. | Amidinophenyl-pyrrolidines, -pyrrolines, and -isoxazolidines and derivatives thereof |
| US6602864B1 (en) * | 1996-12-13 | 2003-08-05 | Aventis Pharma Deutschland Gmbh | Sulfonic acid or sulfonylamino N-(heteroaralkyl)-azaheterocyclylamide compounds |
| DK0944386T3 (da) * | 1996-12-13 | 2003-01-27 | Aventis Pharma Inc | Sulfonsyre- eller sulfonylamino-N-(heteroaralkyl)-azaheterocyclylamid-forbindelser |
| US6359134B1 (en) | 1997-05-30 | 2002-03-19 | Takeda Chemical Industries, Ltd. | Sulfonamide derivatives, their production and use |
| ZA985247B (en) * | 1997-06-19 | 1999-12-17 | Du Pont Merck Pharma | Guanidine mimics as factor Xa inhibitors. |
| KR20010015639A (ko) | 1997-09-30 | 2001-02-26 | 스즈키 다다시 | 술포닐 유도체 |
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| CA2314401A1 (en) * | 1997-12-22 | 1999-07-01 | Du Pont Pharmaceuticals Company | Nitrogen containing heteroaromatics with ortho-substituted p1's as factor xa inhibitors |
| WO1999037304A1 (en) * | 1998-01-27 | 1999-07-29 | Aventis Pharmaceuticals Products Inc. | SUBSTITUTED OXOAZAHETEROCYCLYL FACTOR Xa INHIBITORS |
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| US6291514B1 (en) | 1998-02-09 | 2001-09-18 | 3-Dimensional Pharmaceuticals, Inc. | Heteroaryl amidines, methylamidines and guanidines, preparation thereof, and use thereof as protease inhibitors |
| US6747023B1 (en) * | 1998-08-11 | 2004-06-08 | Daiichi Pharmaceutical Co., Ltd. | Sulfonyl derivatives |
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| DE19909237A1 (de) * | 1999-03-03 | 2000-09-07 | Merck Patent Gmbh | Pyrazol-3-on-derivate |
| US6794412B1 (en) * | 1999-03-11 | 2004-09-21 | Bristol-Myers Squibb Pharma Company | Treatment of thrombosis by combined use of a factor Xa inhibitor and aspirin |
| JP2001026506A (ja) * | 1999-04-28 | 2001-01-30 | Takeda Chem Ind Ltd | スルホンアミド誘導体 |
| US6586617B1 (en) | 1999-04-28 | 2003-07-01 | Sumitomo Chemical Takeda Agro Company, Limited | Sulfonamide derivatives |
| ATE325114T1 (de) | 1999-06-22 | 2006-06-15 | Takeda Pharmaceutical | Acylhydrazinderivate, verfahren zu ihrer herstellung und ihre verwendung |
| CZ2002323A3 (cs) * | 1999-07-28 | 2002-05-15 | Aventis Pharmaceuticals Products Inc. | Substituované oxoazaheterocyklylové sloučeniny a farmaceutické prostředky, které je obsahují |
| US6544981B2 (en) * | 2000-06-09 | 2003-04-08 | Bristol-Myers Squibb Company | Lactam inhibitors of factor Xa and method |
| US6511973B2 (en) * | 2000-08-02 | 2003-01-28 | Bristol-Myers Squibb Co. | Lactam inhibitors of FXa and method |
| ATE338030T1 (de) | 2000-09-11 | 2006-09-15 | Genentech Inc | Amidine-inhibitoren der serine-proteasen |
| EP1340753B1 (en) * | 2000-11-08 | 2006-01-11 | Takeda Pharmaceutical Company Limited | Carbamate derivatives, process for producing the same and use thereof |
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| RS20100015A (sr) * | 2001-01-26 | 2010-12-31 | Schering Corporation | Kombinacija aktivatora receptora aktiviranog peroksizom- proliferatorom (ppar) fenofibrata sa inhibitorom apsorpcije sterola ezetimibom za vaskularne indikacije |
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| EP1628954A2 (en) | 2003-05-20 | 2006-03-01 | Genentech, Inc. | Acylsulfamide inhibitors of factor viia |
| RU2364587C2 (ru) * | 2003-10-29 | 2009-08-20 | Элан Фармасьютикалз, Инк. | N-замещенные бензолсульфонамиды |
| EP1533298A1 (en) | 2003-11-21 | 2005-05-25 | Newron Pharmaceuticals S.p.A. | 3-aminopyrrolidone derivatives |
| TWI396686B (zh) | 2004-05-21 | 2013-05-21 | Takeda Pharmaceutical | 環狀醯胺衍生物、以及其製品和用法 |
| US8524715B2 (en) * | 2004-11-23 | 2013-09-03 | Astrazeneca Ab | Phenoxyacetic acid derivatives useful for treating respiratory diseases |
| JP2008540539A (ja) | 2005-05-10 | 2008-11-20 | バーテックス ファーマシューティカルズ インコーポレイテッド | イオンチャンネルの調節因子としての二環系誘導体 |
| US11034669B2 (en) | 2018-11-30 | 2021-06-15 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4121947A1 (de) * | 1991-07-03 | 1993-01-07 | Basf Ag | 2-(3-(4-amidino-phenyl))-propionsaeurederivate, ihre herstellung und verwendung |
| AU2869092A (en) * | 1991-10-11 | 1993-05-03 | Smithkline Beecham Corporation | Heterocyclic 3-phenylpyrrolidin-2-ones, their preparation and use for the manufacture of a medicament for inhibiting tumor necrosis factor production |
| JPH05201971A (ja) * | 1992-01-28 | 1993-08-10 | Hokuriku Seiyaku Co Ltd | 環状アミン含有ベンゼンスルホンアミド誘導体 |
| US5665754A (en) * | 1993-09-20 | 1997-09-09 | Glaxo Wellcome Inc. | Substituted pyrrolidines |
| AU7665694A (en) * | 1993-09-21 | 1995-04-10 | Yamanouchi Pharmaceutical Co., Ltd. | N-(3-pyrrolidinyl)benzamide derivative |
| FR2714378B1 (fr) * | 1993-12-24 | 1996-03-15 | Sanofi Sa | Dérivés de l'indol-2-one substitués en 3 par un groupe azoté, leur préparation, les compositions pharmaceutiques en contenant. |
-
1995
- 1995-06-07 US US08/481,024 patent/US5612353A/en not_active Expired - Lifetime
-
1996
- 1996-06-07 SK SK1606-97A patent/SK160697A3/sk unknown
- 1996-06-07 CN CN96194489A patent/CN1190395A/zh active Pending
- 1996-06-07 BR BR9608405A patent/BR9608405A/pt not_active Application Discontinuation
- 1996-06-07 JP JP50202997A patent/JP4312829B2/ja not_active Expired - Fee Related
- 1996-06-07 SI SI9620093A patent/SI9620093A/sl unknown
- 1996-06-07 AP APAP/P/1997/001144A patent/AP799A/en active
- 1996-06-07 HU HU9801882A patent/HUP9801882A3/hu unknown
- 1996-06-07 EA EA199800043A patent/EA000700B1/ru not_active IP Right Cessation
- 1996-06-07 EP EP96919298A patent/EP0853618B1/en not_active Expired - Lifetime
- 1996-06-07 CA CA002223403A patent/CA2223403C/en not_active Expired - Fee Related
- 1996-06-07 AT AT96919298T patent/ATE520655T1/de not_active IP Right Cessation
- 1996-06-07 KR KR1019970708866A patent/KR100291711B1/ko not_active Expired - Fee Related
- 1996-06-07 WO PCT/US1996/009816 patent/WO1996040679A1/en not_active Ceased
- 1996-06-07 AU AU61669/96A patent/AU714319B2/en not_active Ceased
- 1996-06-07 PL PL96323780A patent/PL323780A1/xx unknown
- 1996-06-07 CZ CZ973853A patent/CZ385397A3/cs unknown
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1997
- 1997-12-03 OA OA70149A patent/OA10752A/en unknown
- 1997-12-08 MX MX9709977A patent/MX9709977A/es not_active IP Right Cessation
- 1997-12-08 NO NO19975762A patent/NO310457B1/no unknown
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1998
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Also Published As
| Publication number | Publication date |
|---|---|
| EA000700B1 (ru) | 2000-02-28 |
| CZ385397A3 (cs) | 1999-05-12 |
| EP0853618B1 (en) | 2011-08-17 |
| SK160697A3 (en) | 1998-11-04 |
| AU6166996A (en) | 1996-12-30 |
| JPH11507368A (ja) | 1999-06-29 |
| BG63628B1 (bg) | 2002-07-31 |
| EA199800043A1 (ru) | 1998-08-27 |
| US5612353A (en) | 1997-03-18 |
| EP0853618A1 (en) | 1998-07-22 |
| CA2223403C (en) | 2002-04-23 |
| AP799A (en) | 2000-01-19 |
| CN1190395A (zh) | 1998-08-12 |
| HUP9801882A3 (en) | 1999-01-28 |
| EP0853618A4 (en) | 2000-03-15 |
| AU714319B2 (en) | 2000-01-06 |
| KR100291711B1 (ko) | 2001-09-17 |
| AP9701144A0 (en) | 1998-01-31 |
| NO975762L (no) | 1998-02-06 |
| NO975762D0 (no) | 1997-12-08 |
| SI9620093A (sl) | 1999-02-28 |
| MX9709977A (es) | 1998-07-31 |
| ATE520655T1 (de) | 2011-09-15 |
| HUP9801882A2 (hu) | 1998-12-28 |
| WO1996040679A1 (en) | 1996-12-19 |
| KR19990022386A (ko) | 1999-03-25 |
| NO310457B1 (no) | 2001-07-09 |
| OA10752A (en) | 2001-07-04 |
| BR9608405A (pt) | 1999-08-24 |
| CA2223403A1 (en) | 1996-12-19 |
| BG102162A (en) | 1998-09-30 |
| PL323780A1 (en) | 1998-04-27 |
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