CN100525766C - 用作平滑肌细胞增殖抑制剂的(咪唑-5-基)甲基-2-喹啉酮衍生物 - Google Patents
用作平滑肌细胞增殖抑制剂的(咪唑-5-基)甲基-2-喹啉酮衍生物 Download PDFInfo
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- CN100525766C CN100525766C CNB2005101163581A CN200510116358A CN100525766C CN 100525766 C CN100525766 C CN 100525766C CN B2005101163581 A CNB2005101163581 A CN B2005101163581A CN 200510116358 A CN200510116358 A CN 200510116358A CN 100525766 C CN100525766 C CN 100525766C
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- methyl
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- 210000000329 smooth muscle myocyte Anatomy 0.000 title claims abstract description 27
- 230000004663 cell proliferation Effects 0.000 title claims abstract description 23
- 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 180
- 229910052739 hydrogen Inorganic materials 0.000 claims description 61
- 239000001257 hydrogen Substances 0.000 claims description 61
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 18
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- 229910052760 oxygen Inorganic materials 0.000 claims description 10
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- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 125000001475 halogen functional group Chemical group 0.000 claims 1
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- 238000002360 preparation method Methods 0.000 description 20
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- 108010037444 diisopropylglutathione ester Proteins 0.000 description 11
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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 11
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 10
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- 210000004027 cell Anatomy 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
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- 239000010410 layer Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
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- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 7
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- 125000000524 functional group Chemical group 0.000 description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
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- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 6
- 235000001014 amino acid Nutrition 0.000 description 6
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- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 description 6
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- 239000002552 dosage form Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 6
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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
-
- 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
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US60/047376 | 1997-06-02 |
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CN100525766C true CN100525766C (zh) | 2009-08-12 |
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CNB98805700XA Expired - Lifetime CN1231215C (zh) | 1997-06-02 | 1998-05-25 | (咪唑-5-基)甲基-2-喹啉酮衍生物用作平滑肌细胞增殖抑制剂 |
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CNB98805700XA Expired - Lifetime CN1231215C (zh) | 1997-06-02 | 1998-05-25 | (咪唑-5-基)甲基-2-喹啉酮衍生物用作平滑肌细胞增殖抑制剂 |
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