CZ291217B6 - N-Substituované deriváty chinolinu, způsob jejich přípravy, tyto deriváty jako léčiva, farmaceutické kompozice tyto deriváty obsahující a pouľití těchto derivátů pro přípravu léčiva - Google Patents
N-Substituované deriváty chinolinu, způsob jejich přípravy, tyto deriváty jako léčiva, farmaceutické kompozice tyto deriváty obsahující a pouľití těchto derivátů pro přípravu léčiva Download PDFInfo
- Publication number
- CZ291217B6 CZ291217B6 CS1992357A CS35792A CZ291217B6 CZ 291217 B6 CZ291217 B6 CZ 291217B6 CS 1992357 A CS1992357 A CS 1992357A CS 35792 A CS35792 A CS 35792A CZ 291217 B6 CZ291217 B6 CZ 291217B6
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- formula
- methyl
- butyl
- compound
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- 238000002360 preparation method Methods 0.000 title claims description 43
- 238000000034 method Methods 0.000 title claims description 22
- 239000003814 drug Substances 0.000 title claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 230000008569 process Effects 0.000 title claims description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 117
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 34
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 10
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 7
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- 206010019280 Heart failures Diseases 0.000 claims abstract description 4
- 208000001647 Renal Insufficiency Diseases 0.000 claims abstract description 4
- 206010039966 Senile dementia Diseases 0.000 claims abstract description 4
- 230000036506 anxiety Effects 0.000 claims abstract description 4
- 208000037849 arterial hypertension Diseases 0.000 claims abstract description 4
- 230000002496 gastric effect Effects 0.000 claims abstract description 4
- 201000006370 kidney failure Diseases 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- -1 N-substituted quinoline Chemical class 0.000 claims description 52
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 52
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 30
- 239000011707 mineral Substances 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 18
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
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- 150000007524 organic acids Chemical class 0.000 claims description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 claims description 7
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- 125000001424 substituent group Chemical group 0.000 claims description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
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- JBSKLLYOAXSQKE-UHFFFAOYSA-N 2-[4-[[3-butyl-4-oxo-7-(2-oxo-2-pyrrolidin-1-ylethyl)quinolin-1-yl]methyl]phenyl]benzoic acid Chemical compound C12=CC(CC(=O)N3CCCC3)=CC=C2C(=O)C(CCCC)=CN1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O JBSKLLYOAXSQKE-UHFFFAOYSA-N 0.000 claims description 2
- DZZXAHOEVWFVBQ-UHFFFAOYSA-N 2-[4-[[3-butyl-6-(2-carboxyethenyl)-4-oxoquinolin-1-yl]methyl]phenyl]benzoic acid Chemical compound C12=CC=C(C=CC(O)=O)C=C2C(=O)C(CCCC)=CN1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O DZZXAHOEVWFVBQ-UHFFFAOYSA-N 0.000 claims description 2
- XOJUTGWJQCUOCQ-UHFFFAOYSA-N 2-[4-[[3-butyl-7-(carboxymethyl)-4-oxoquinolin-1-yl]methyl]phenyl]benzoic acid Chemical compound C12=CC(CC(O)=O)=CC=C2C(=O)C(CCCC)=CN1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O XOJUTGWJQCUOCQ-UHFFFAOYSA-N 0.000 claims description 2
- SRCSOIXLHIUMOG-UHFFFAOYSA-N 3-butyl-4-oxo-1-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]quinoline-8-carboxylic acid Chemical compound C12=C(C(O)=O)C=CC=C2C(=O)C(CCCC)=CN1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 SRCSOIXLHIUMOG-UHFFFAOYSA-N 0.000 claims description 2
- HLAYLOOJBAJIRU-UHFFFAOYSA-N 5-biphenyl-2-yl-1H-tetrazole Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=NN=NN1 HLAYLOOJBAJIRU-UHFFFAOYSA-N 0.000 claims description 2
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
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- XTZTYMXIYRLXMN-UHFFFAOYSA-N methyl 2-[4-[(3-butyl-4-oxoquinolin-1-yl)methyl]phenyl]benzoate Chemical compound C12=CC=CC=C2C(=O)C(CCCC)=CN1CC(C=C1)=CC=C1C1=CC=CC=C1C(=O)OC XTZTYMXIYRLXMN-UHFFFAOYSA-N 0.000 description 1
- AWIIDACYRUDQKA-UHFFFAOYSA-N methyl 2-[4-[(3-butyl-4-sulfanylidenequinolin-1-yl)methyl]phenyl]benzoate Chemical compound C12=CC=CC=C2C(=S)C(CCCC)=CN1CC(C=C1)=CC=C1C1=CC=CC=C1C(=O)OC AWIIDACYRUDQKA-UHFFFAOYSA-N 0.000 description 1
- ZCKDADHKXVFIDM-UHFFFAOYSA-N methyl 3-butyl-4-oxo-1h-quinoline-7-carboxylate Chemical compound COC(=O)C1=CC=C2C(=O)C(CCCC)=CNC2=C1 ZCKDADHKXVFIDM-UHFFFAOYSA-N 0.000 description 1
- LZXXNPOYQCLXRS-UHFFFAOYSA-N methyl 4-aminobenzoate Chemical compound COC(=O)C1=CC=C(N)C=C1 LZXXNPOYQCLXRS-UHFFFAOYSA-N 0.000 description 1
- HNJJWQGZBAUTHL-UHFFFAOYSA-N methyl 5-(bromomethyl)-2-phenylbenzoate Chemical compound COC(=O)C1=CC(CBr)=CC=C1C1=CC=CC=C1 HNJJWQGZBAUTHL-UHFFFAOYSA-N 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000001457 vasomotor Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 230000009278 visceral effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three 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
- C07D237/14—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/02—Drugs for genital or sexual disorders; Contraceptives for disorders of the vagina
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/20—Hypnotics; Sedatives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- 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
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
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- 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
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/28—Cinnolines
-
- 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
- C07D401/10—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 aromatic rings
-
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Urology & Nephrology (AREA)
- Ophthalmology & Optometry (AREA)
- Anesthesiology (AREA)
- Gynecology & Obstetrics (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9101372A FR2672597B1 (fr) | 1991-02-07 | 1991-02-07 | Nouveaux derives n-substitues de la quinoleine, leur procede de preparation, les nouveaux intermediaires obtenus, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant. |
| FR9110433A FR2680511B1 (fr) | 1991-08-20 | 1991-08-20 | Derives n-substitues de la quinoleine, leur procede de preparation, intermediaires obtenus, leur application comme medicaments et les compositions les renfermant. |
| FR9114282A FR2684671B1 (fr) | 1991-11-20 | 1991-11-20 | Nouveaux derives de la quinoleine, leur procede de preparation et intermediaires et leur application a titre de medicaments. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ35792A3 CZ35792A3 (en) | 1993-10-13 |
| CZ291217B6 true CZ291217B6 (cs) | 2003-01-15 |
Family
ID=27252397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS1992357A CZ291217B6 (cs) | 1991-02-07 | 1992-02-07 | N-Substituované deriváty chinolinu, způsob jejich přípravy, tyto deriváty jako léčiva, farmaceutické kompozice tyto deriváty obsahující a pouľití těchto derivátů pro přípravu léčiva |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US5985894A (en, 2012) |
| EP (1) | EP0498721B1 (en, 2012) |
| JP (1) | JP3599350B2 (en, 2012) |
| KR (1) | KR100334208B1 (en, 2012) |
| CN (1) | CN1064076A (en, 2012) |
| AT (1) | ATE187964T1 (en, 2012) |
| BR (1) | BR9200432A (en, 2012) |
| CA (1) | CA2060843A1 (en, 2012) |
| CZ (1) | CZ291217B6 (en, 2012) |
| DE (1) | DE69230449T2 (en, 2012) |
| DK (1) | DK0498721T3 (en, 2012) |
| ES (1) | ES2141098T3 (en, 2012) |
| FI (1) | FI103574B1 (en, 2012) |
| GR (1) | GR3032711T3 (en, 2012) |
| HU (1) | HUT64524A (en, 2012) |
| IE (1) | IE920395A1 (en, 2012) |
| IL (1) | IL100555A (en, 2012) |
| MA (1) | MA22410A1 (en, 2012) |
| NZ (1) | NZ241546A (en, 2012) |
| OA (1) | OA09528A (en, 2012) |
| PL (1) | PL169672B1 (en, 2012) |
| PT (1) | PT498721E (en, 2012) |
| RU (1) | RU2125047C1 (en, 2012) |
| TW (1) | TW214554B (en, 2012) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL101860A0 (en) * | 1991-05-31 | 1992-12-30 | Ici Plc | Heterocyclic derivatives |
| GB9121727D0 (en) * | 1991-10-14 | 1991-11-27 | Ici Plc | Heterocyclic compounds |
| JPH05310732A (ja) * | 1992-03-12 | 1993-11-22 | Mitsubishi Kasei Corp | シンノリン−３−カルボン酸誘導体 |
| IT1312107B1 (it) * | 1999-05-14 | 2002-04-04 | Umberto Cornelli | Glicosaminoglicani aventi peso molecolare medio di 2400 d atti altrattamento della demenza senile |
| SE9903028D0 (sv) | 1999-08-27 | 1999-08-27 | Astra Ab | New use |
| US6822098B2 (en) * | 2000-08-29 | 2004-11-23 | Yamanouchi Pharmaceutical Co., Ltd. | Ester or amide derivatives |
| EG24415A (en) * | 2002-03-07 | 2009-05-25 | Novartis Ag | Quinoline derivatives |
| WO2004028634A1 (en) * | 2002-09-25 | 2004-04-08 | The Board Of Trustees Of The University Of Illinois | Method and composition for treating alzheimer's disease and dementias of vascular origin |
| TWI248928B (en) | 2002-11-20 | 2006-02-11 | Japan Tobacco Inc | 4-oxoquinoline compound and use thereof as HIV integrase inhibitor |
| MY134672A (en) | 2004-05-20 | 2007-12-31 | Japan Tobacco Inc | Stable crystal of 4-oxoquinoline compound |
| WO2005113509A1 (en) | 2004-05-20 | 2005-12-01 | Japan Tobacco Inc. | Novel 4-oxoquinoline compound and use thereof as hiv integrase inhibitor |
| US8633219B2 (en) | 2004-05-21 | 2014-01-21 | Japan Tobacco Inc. | Combination therapy |
| US20070071679A1 (en) * | 2005-09-29 | 2007-03-29 | Hilakivi Ilkka T | Methylamine risks and treatment of hyperactivity, depression, and alcoholism with epinephrine-N-quinolines |
| EP2452682A1 (en) * | 2006-02-01 | 2012-05-16 | Japan Tobacco, Inc. | Use of 6-(3-chloro-2-fluorobenzyl)-1-[(2s)-1-hydroxy-3-methylbutan-2-yl]-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid or salt thereof for treating retrovirus infection |
| EA017861B9 (ru) | 2006-03-06 | 2014-05-30 | Джапан Тобакко Инк. | Способ получения 4-оксохинолинового соединения |
| US8138191B2 (en) | 2007-01-11 | 2012-03-20 | Critical Outcome Technologies Inc. | Inhibitor compounds and cancer treatment methods |
| DK2170930T3 (da) | 2007-06-04 | 2012-11-05 | Synergy Pharmaceuticals Inc | Agonister af guanylatcyclase, anvendelige til behandlingen af gastrointestinale sygdomme, inflammation, cancer og andre sygdomme |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| US8034782B2 (en) | 2008-07-16 | 2011-10-11 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| GB0716532D0 (en) | 2007-08-24 | 2007-10-03 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| EP2328910B1 (en) | 2008-06-04 | 2014-08-06 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| TWI492943B (zh) * | 2008-12-05 | 2015-07-21 | 大塚製藥股份有限公司 | 喹啉酮化合物及藥學組成物（二） |
| EP3235818A3 (en) | 2010-04-01 | 2018-03-14 | Critical Outcome Technologies, Inc. | Compounds for the treatment of hiv |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| US9180242B2 (en) | 2012-05-17 | 2015-11-10 | Tandem Diabetes Care, Inc. | Methods and devices for multiple fluid transfer |
| US9173998B2 (en) | 2013-03-14 | 2015-11-03 | Tandem Diabetes Care, Inc. | System and method for detecting occlusions in an infusion pump |
| AU2014235209B2 (en) | 2013-03-15 | 2018-06-14 | Bausch Health Ireland Limited | Guanylate cyclase receptor agonists combined with other drugs |
| EP2970384A1 (en) | 2013-03-15 | 2016-01-20 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| KR102272746B1 (ko) | 2013-06-05 | 2021-07-08 | 보슈 헬스 아일랜드 리미티드 | 구아닐레이트 사이클라제 c의 초순수 작용제, 및 이의 제조 및 사용 방법 |
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| US2555943A (en) * | 1947-06-28 | 1951-06-05 | Sterling Drug Inc | Dihalo-4-(aliphatic tertiaryamino-alkylamino)quinolines |
| US3002001A (en) * | 1958-04-03 | 1961-09-26 | Sterling Drug Inc | 4-alkylimino-1-[aromatic-(lower - alkyl)]-1,4-dihydroquinolines and their preparation |
| GB1419788A (en) * | 1972-08-02 | 1975-12-31 | Pfizer | Herbicidal method using 2-trifuluromethyl-4-quinolinols |
| GB1432649A (en, 2012) * | 1973-09-07 | 1976-04-22 | Ici Ltd | |
| GB1472767A (en) * | 1974-11-07 | 1977-05-04 | Ici Ltd | Process for the preparation of cinnoline derivatives |
| FR2377400A2 (fr) * | 1977-01-18 | 1978-08-11 | Roussel Uclaf | Nouveaux derives de l'acide 3-quinoleine carboxylique, leur procede de preparation et leur application comme medicament |
| NZ193167A (en) * | 1979-03-27 | 1984-08-24 | Boots Co Plc | Quinoline derivatives and pharmaceutical compositions |
| JPS58219166A (ja) * | 1982-06-14 | 1983-12-20 | Nippon Shinyaku Co Ltd | ４−キノロン誘導体 |
| SU1421374A1 (ru) * | 1987-03-31 | 1988-09-07 | Предприятие П/Я М-5671 | Устройство дл регенерации мелкопористых фильтроэлементов |
| US4920131A (en) * | 1987-11-03 | 1990-04-24 | Rorer Pharmaceutical Corp. | Quinoline derivatives and use thereof as antagonists of leukotriene D4 |
| US4880804A (en) * | 1988-01-07 | 1989-11-14 | E. I. Du Pont De Nemours And Company | Angiotensin II receptor blocking benzimidazoles |
| DE68917024D1 (de) * | 1988-05-24 | 1994-09-01 | Kirin Brewery | 4(1H)-Chinolonderivate. |
| US4918081A (en) * | 1988-06-20 | 1990-04-17 | Rorer Pharmaceutical Corp. | Quinoline derivatives and use thereof as antagonists of leukotriene d4 |
| US5064825A (en) * | 1989-06-01 | 1991-11-12 | Merck & Co., Inc. | Angiotensin ii antagonists |
| US4959363A (en) * | 1989-06-23 | 1990-09-25 | Sterling Drug Inc. | Quinolonecarboxamide compounds, their preparation and use as antivirals. |
| IE902909A1 (en) * | 1989-08-11 | 1991-02-27 | Ici Plc | Nitrogen compounds |
| CA2037630C (en) * | 1990-03-07 | 2001-07-03 | Akira Morimoto | Nitrogen-containing heterocylic compounds, their production and use |
| US5157040A (en) * | 1991-04-05 | 1992-10-20 | Merck & Co., Inc. | Substituted quinolines as angiotensin ii antagonists |
| US5162325A (en) * | 1991-05-07 | 1992-11-10 | Merck & Co., Inc. | Angiotensin ii antagonists incorporating a substituted benzyl element |
| US5162340A (en) * | 1991-05-10 | 1992-11-10 | Merck & Co., Inc. | Substituted 1-(2h)-isoquinolinones bearing acidic functional groups as angiotensin ii antagonists |
-
1991
- 1991-12-30 IL IL10055591A patent/IL100555A/xx not_active IP Right Cessation
-
1992
- 1992-02-04 JP JP04759492A patent/JP3599350B2/ja not_active Expired - Fee Related
- 1992-02-04 MA MA22697A patent/MA22410A1/fr unknown
- 1992-02-05 AT AT92400294T patent/ATE187964T1/de not_active IP Right Cessation
- 1992-02-05 ES ES92400294T patent/ES2141098T3/es not_active Expired - Lifetime
- 1992-02-05 PT PT92400294T patent/PT498721E/pt unknown
- 1992-02-05 EP EP92400294A patent/EP0498721B1/fr not_active Expired - Lifetime
- 1992-02-05 DE DE69230449T patent/DE69230449T2/de not_active Expired - Fee Related
- 1992-02-05 DK DK92400294T patent/DK0498721T3/da active
- 1992-02-06 IE IE039592A patent/IE920395A1/en unknown
- 1992-02-06 RU SU5010859A patent/RU2125047C1/ru active
- 1992-02-06 HU HU9200367A patent/HUT64524A/hu unknown
- 1992-02-06 FI FI920504A patent/FI103574B1/fi active
- 1992-02-06 KR KR1019920001715A patent/KR100334208B1/ko not_active Expired - Fee Related
- 1992-02-07 CN CN92100765A patent/CN1064076A/zh active Pending
- 1992-02-07 PL PL92293414A patent/PL169672B1/pl unknown
- 1992-02-07 CA CA002060843A patent/CA2060843A1/fr not_active Abandoned
- 1992-02-07 NZ NZ241546A patent/NZ241546A/en unknown
- 1992-02-07 CZ CS1992357A patent/CZ291217B6/cs not_active IP Right Cessation
- 1992-02-07 OA OA60146A patent/OA09528A/fr unknown
- 1992-02-07 BR BR929200432A patent/BR9200432A/pt not_active Application Discontinuation
- 1992-02-18 TW TW081101181A patent/TW214554B/zh active
-
1997
- 1997-11-04 US US08/964,182 patent/US5985894A/en not_active Expired - Fee Related
-
2000
- 2000-02-18 GR GR20000400410T patent/GR3032711T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US5985894A (en) | 1999-11-16 |
| TW214554B (en, 2012) | 1993-10-11 |
| ES2141098T3 (es) | 2000-03-16 |
| DE69230449D1 (de) | 2000-01-27 |
| EP0498721A1 (fr) | 1992-08-12 |
| DE69230449T2 (de) | 2000-08-03 |
| OA09528A (fr) | 1992-11-15 |
| KR920016432A (ko) | 1992-09-24 |
| PL293414A1 (en) | 1993-05-04 |
| MA22410A1 (fr) | 1992-10-01 |
| CZ35792A3 (en) | 1993-10-13 |
| IE920395A1 (en) | 1992-08-12 |
| RU2125047C1 (ru) | 1999-01-20 |
| JP3599350B2 (ja) | 2004-12-08 |
| FI920504A0 (fi) | 1992-02-06 |
| BR9200432A (pt) | 1992-10-13 |
| NZ241546A (en) | 1995-03-28 |
| FI103574B (fi) | 1999-07-30 |
| HU9200367D0 (en) | 1992-04-28 |
| IL100555A (en) | 2000-08-31 |
| EP0498721B1 (fr) | 1999-12-22 |
| IL100555A0 (en) | 1992-09-06 |
| PL169672B1 (pl) | 1996-08-30 |
| ATE187964T1 (de) | 2000-01-15 |
| FI920504A7 (fi) | 1992-08-08 |
| GR3032711T3 (en) | 2000-06-30 |
| CA2060843A1 (fr) | 1992-08-08 |
| PT498721E (pt) | 2000-04-28 |
| FI103574B1 (fi) | 1999-07-30 |
| JPH04360872A (ja) | 1992-12-14 |
| HUT64524A (en) | 1994-01-28 |
| DK0498721T3 (da) | 2000-06-26 |
| CN1064076A (zh) | 1992-09-02 |
| KR100334208B1 (ko) | 2002-08-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD00 | Pending as of 2000-06-30 in czech republic | ||
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20040207 |