NZ501401A - (Imidazol-5-yl)methyl-2-quinolinone derivatives as inhibitors of smooth muscle cell proliferation - Google Patents
(Imidazol-5-yl)methyl-2-quinolinone derivatives as inhibitors of smooth muscle cell proliferationInfo
- Publication number
- NZ501401A NZ501401A NZ501401A NZ50140198A NZ501401A NZ 501401 A NZ501401 A NZ 501401A NZ 501401 A NZ501401 A NZ 501401A NZ 50140198 A NZ50140198 A NZ 50140198A NZ 501401 A NZ501401 A NZ 501401A
- Authority
- NZ
- New Zealand
- Prior art keywords
- 6alkyl
- hydrogen
- formula
- 6alkyloxy
- galkyl
- Prior art date
Links
- 210000000329 smooth muscle myocyte Anatomy 0.000 title claims abstract description 23
- 230000004663 cell proliferation Effects 0.000 title claims abstract description 14
- 239000003112 inhibitor Substances 0.000 title description 5
- IKMMPHALUZQNMN-UHFFFAOYSA-N 3-(1h-imidazol-5-ylmethyl)-1h-quinolin-2-one Chemical class O=C1NC2=CC=CC=C2C=C1CC1=CN=CN1 IKMMPHALUZQNMN-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 140
- 239000001257 hydrogen Substances 0.000 claims abstract description 89
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 89
- -1 C1-6alkyloxycarbonyl Chemical group 0.000 claims abstract description 58
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 53
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000001301 oxygen Substances 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 239000003814 drug Substances 0.000 claims abstract description 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 125000004951 trihalomethoxy group Chemical group 0.000 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052717 sulfur Chemical group 0.000 claims abstract description 5
- 239000011593 sulfur Chemical group 0.000 claims abstract description 5
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 3
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 51
- 235000011468 Albizia julibrissin Nutrition 0.000 claims description 39
- 241001070944 Mimosa Species 0.000 claims description 39
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 29
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- 238000000576 coating method Methods 0.000 claims description 16
- 239000011248 coating agent Substances 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 13
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 10
- 230000002062 proliferating effect Effects 0.000 claims description 10
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- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims description 4
- 230000006715 negative regulation of smooth muscle cell proliferation Effects 0.000 claims description 4
- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 8
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 102
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- 239000002904 solvent Substances 0.000 description 44
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 11
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
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- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
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- 229960005356 urokinase Drugs 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
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- 235000005074 zinc chloride Nutrition 0.000 description 1
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- 235000004835 α-tocopherol Nutrition 0.000 description 1
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Classifications
-
- 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
- A61K31/47—Quinolines; Isoquinolines
-
- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US4737697P | 1997-06-02 | 1997-06-02 | |
PCT/EP1998/003182 WO1998055124A1 (en) | 1997-06-02 | 1998-05-25 | (imidazol-5-yl)methyl-2-quinolinone derivatives as inhibitors of smooth muscle cell proliferation |
Publications (1)
Publication Number | Publication Date |
---|---|
NZ501401A true NZ501401A (en) | 2002-03-28 |
Family
ID=21948611
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NZ501401A NZ501401A (en) | 1997-06-02 | 1998-05-25 | (Imidazol-5-yl)methyl-2-quinolinone derivatives as inhibitors of smooth muscle cell proliferation |
Country Status (22)
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-
1998
- 1998-05-25 JP JP50144099A patent/JP4209472B2/ja not_active Expired - Lifetime
- 1998-05-25 CN CNB2005101163581A patent/CN100525766C/zh not_active Expired - Lifetime
- 1998-05-25 ES ES98928332T patent/ES2182327T3/es not_active Expired - Lifetime
- 1998-05-25 BR BR9810423-3A patent/BR9810423A/pt not_active Application Discontinuation
- 1998-05-25 CN CNB98805700XA patent/CN1231215C/zh not_active Expired - Lifetime
- 1998-05-25 IL IL13321298A patent/IL133212A/en not_active IP Right Cessation
- 1998-05-25 CA CA002290992A patent/CA2290992C/en not_active Expired - Lifetime
- 1998-05-25 EP EP98928332A patent/EP0988038B1/en not_active Expired - Lifetime
- 1998-05-25 RU RU2000100032/14A patent/RU2209066C2/ru active
- 1998-05-25 AU AU80207/98A patent/AU740603B2/en not_active Expired
- 1998-05-25 DE DE69807222T patent/DE69807222T2/de not_active Expired - Lifetime
- 1998-05-25 TR TR1999/02923T patent/TR199902923T2/xx unknown
- 1998-05-25 NZ NZ501401A patent/NZ501401A/en not_active IP Right Cessation
- 1998-05-25 PT PT98928332T patent/PT988038E/pt unknown
- 1998-05-25 AT AT98928332T patent/ATE222104T1/de active
- 1998-05-25 KR KR10-1999-7010744A patent/KR100517832B1/ko not_active IP Right Cessation
- 1998-05-25 DK DK98928332T patent/DK0988038T3/da active
- 1998-05-25 WO PCT/EP1998/003182 patent/WO1998055124A1/en active IP Right Grant
- 1998-05-28 ID IDW991506A patent/ID24675A/id unknown
- 1998-06-01 ZA ZA9804700A patent/ZA984700B/xx unknown
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1999
- 1999-05-25 US US09/445,009 patent/US6365600B1/en not_active Expired - Lifetime
- 1999-12-01 NO NO19995883A patent/NO318834B1/no not_active IP Right Cessation
-
2000
- 2000-07-08 HK HK00104198A patent/HK1025046A1/xx not_active IP Right Cessation
-
2001
- 2001-11-28 US US09/996,147 patent/US6743805B2/en not_active Expired - Lifetime
-
2003
- 2003-06-18 US US10/464,570 patent/US6734194B2/en not_active Expired - Lifetime
-
2004
- 2004-04-14 US US10/823,862 patent/US7253183B2/en not_active Expired - Lifetime
-
2006
- 2006-08-16 HK HK06109112.8A patent/HK1088820A1/xx not_active IP Right Cessation
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