AU740603B2 - (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 proliferation Download PDFInfo
- Publication number
- AU740603B2 AU740603B2 AU80207/98A AU8020798A AU740603B2 AU 740603 B2 AU740603 B2 AU 740603B2 AU 80207/98 A AU80207/98 A AU 80207/98A AU 8020798 A AU8020798 A AU 8020798A AU 740603 B2 AU740603 B2 AU 740603B2
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- Australia
- Prior art keywords
- sub
- alkyl
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- hydrogen
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- 210000000329 smooth muscle myocyte Anatomy 0.000 title claims abstract description 25
- 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
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 149
- 150000001875 compounds Chemical class 0.000 claims abstract description 146
- 239000001257 hydrogen Substances 0.000 claims abstract description 110
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 110
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 74
- -1 amino, hydroxycarbonyl Chemical group 0.000 claims abstract description 63
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 36
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 34
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000001301 oxygen Substances 0.000 claims abstract description 14
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- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
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- 239000011593 sulfur Chemical group 0.000 claims abstract description 6
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims abstract description 5
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- 238000000034 method Methods 0.000 claims description 36
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
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- 150000003839 salts Chemical class 0.000 claims description 21
- 238000000576 coating method Methods 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 239000011248 coating agent Substances 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
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- 241001465754 Metazoa Species 0.000 claims description 14
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 235000001014 amino acid Nutrition 0.000 description 8
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- 239000010410 layer Substances 0.000 description 7
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- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 7
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Classifications
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- 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
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- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
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- 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 (3)
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|---|---|---|---|
| US4737697P | 1997-06-02 | 1997-06-02 | |
| US60/047376 | 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 (2)
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| AU8020798A AU8020798A (en) | 1998-12-21 |
| AU740603B2 true AU740603B2 (en) | 2001-11-08 |
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| AU80207/98A Expired AU740603B2 (en) | 1997-06-02 | 1998-05-25 | (imidazol-5-yl)methyl-2-quinolinone derivatives as inhibitors of smooth muscle cell proliferation |
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| US20020099438A1 (en) * | 1998-04-15 | 2002-07-25 | Furst Joseph G. | Irradiated stent coating |
| US20030040790A1 (en) * | 1998-04-15 | 2003-02-27 | Furst Joseph G. | Stent coating |
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| ES2237125T3 (es) * | 1998-08-27 | 2005-07-16 | Pfizer Products Inc. | Derivados de quinolin-2-ona utiles como agentes anticancerigenos. |
| IL143859A0 (en) * | 1998-12-23 | 2002-04-21 | Janssen Pharmaceutica Nv | 1,2-annelated quinoline derivatives |
| EP1150973B1 (en) | 1999-02-11 | 2005-06-15 | Pfizer Products Inc. | Heteroaryl-substituted quinolin-2-one derivatives useful as anticancer agents |
| DE60008206T2 (de) | 1999-11-30 | 2004-12-02 | Pfizer Products Inc., Groton | Chinolinderivate verwendbar zur Hemmung der Farnesyl-Protein Transferase |
| US6844357B2 (en) * | 2000-05-01 | 2005-01-18 | Pfizer Inc. | Substituted quinolin-2-one derivatives useful as antiproliferative agents |
| JO2361B1 (en) | 2000-06-22 | 2006-12-12 | جانسين فارماسيوتيكا ان. في | Enaniumer 1,2-anylated quinoline inhibitor for the transporter - farnesyl |
| ES2302106T3 (es) | 2000-09-11 | 2008-07-01 | Novartis Vaccines And Diagnostics, Inc. | Procedimiento de preparacion de derivados de bencimidazol-2-il quinolina. |
| FR2813791B1 (fr) * | 2000-09-14 | 2004-03-12 | Lafon Labor | Utilisation de 2- et 4-quinolones pour inhiber la neo-proliferation intimale |
| WO2002024682A1 (en) | 2000-09-25 | 2002-03-28 | Janssen Pharmaceutica N.V. | Farnesyl transferase inhibiting quinoline and quinazoline derivatives as farnesyl transferase inhibitors |
| AU2001293829A1 (en) * | 2000-09-25 | 2002-04-02 | Janssen Pharmaceutica N.V. | Farnesyl transferase inhibiting 6-((substituted phenyl)methyl)-quinoline and quinazoline derivatives |
| ATE409189T1 (de) | 2000-09-25 | 2008-10-15 | Janssen Pharmaceutica Nv | Farnesyl transferase-hemmende 6- heterocyclylmethyl-chinolin und chinazol-derivate |
| US7067531B2 (en) | 2000-09-25 | 2006-06-27 | Angibaud Patrick Rene | Farnesyl transferase inhibiting 6-heterocyclylmethyl quinolinone derivatives |
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| CA2481480C (en) | 2002-04-15 | 2011-04-12 | Janssen Pharmaceutica N.V. | Farnesyl transferase inhibiting tricyclic quinazoline derivatives substituted with carbon-linked imidazoles or triazoles |
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