OA11010A - Quinoline derivatives - Google Patents
Quinoline derivatives Download PDFInfo
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- OA11010A OA11010A OA9800061A OA9800061A OA11010A OA 11010 A OA11010 A OA 11010A OA 9800061 A OA9800061 A OA 9800061A OA 9800061 A OA9800061 A OA 9800061A OA 11010 A OA11010 A OA 11010A
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- OAPI
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- compound
- formula
- alkyl
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- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title 1
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 204
- 238000000034 method Methods 0.000 claims abstract description 24
- 230000008569 process Effects 0.000 claims abstract description 8
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 5
- -1 sulphonamido Chemical group 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 238000011282 treatment Methods 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 108010040716 Neurokinin-3 Receptors Proteins 0.000 claims description 9
- 102000002003 Neurokinin-3 Receptors Human genes 0.000 claims description 9
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 9
- 239000005557 antagonist Substances 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 8
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000002746 neurokinin 2 receptor antagonist Substances 0.000 claims description 6
- 238000011321 prophylaxis Methods 0.000 claims description 6
- 125000006413 ring segment Chemical group 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000002740 neurokinin 3 receptor antagonist Substances 0.000 claims description 5
- 208000023504 respiratory system disease Diseases 0.000 claims description 5
- 108010040722 Neurokinin-2 Receptors Proteins 0.000 claims description 4
- 102100037342 Substance-K receptor Human genes 0.000 claims description 4
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000005518 carboxamido group Chemical group 0.000 claims description 2
- 125000005544 phthalimido group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical group ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 52
- 150000003839 salts Chemical class 0.000 abstract description 15
- 239000003814 drug Substances 0.000 abstract description 3
- 239000012453 solvate Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 150
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 70
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 58
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 45
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 41
- 235000019439 ethyl acetate Nutrition 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 31
- 238000005481 NMR spectroscopy Methods 0.000 description 30
- 239000008279 sol Substances 0.000 description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 20
- 239000011780 sodium chloride Substances 0.000 description 20
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- 239000000243 solution Substances 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
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- 238000000921 elemental analysis Methods 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 17
- 229910002027 silica gel Inorganic materials 0.000 description 17
- 229960001866 silicon dioxide Drugs 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 16
- 239000003480 eluent Substances 0.000 description 16
- 238000003818 flash chromatography Methods 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 15
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 239000007787 solid Substances 0.000 description 12
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
- 235000011114 ammonium hydroxide Nutrition 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
- 208000035475 disorder Diseases 0.000 description 10
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- 101800002813 Neurokinin-B Proteins 0.000 description 5
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- WZYBQONKMQQIDY-UHFFFAOYSA-N 3-amino-2-phenylquinoline-4-carboxylic acid Chemical compound N1=C2C=CC=CC2=C(C(O)=O)C(N)=C1C1=CC=CC=C1 WZYBQONKMQQIDY-UHFFFAOYSA-N 0.000 description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 4
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- NHXYSAFTNPANFK-HDMCBQFHSA-N Neurokinin B Chemical compound C([C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)C(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCSC)NC(=O)[C@@H](N)CC(O)=O)C1=CC=CC=C1 NHXYSAFTNPANFK-HDMCBQFHSA-N 0.000 description 4
- 102000046798 Neurokinin B Human genes 0.000 description 4
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
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- 125000001424 substituent group Chemical group 0.000 description 4
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- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
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- 150000007529 inorganic bases Chemical class 0.000 description 1
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- 238000001990 intravenous administration Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- QRFUDVXZHQAEFC-JSSZYCLJSA-N methyl (e)-4-oxo-4-[2-[2-phenyl-4-[[(1s)-1-phenylpropyl]carbamoyl]quinolin-3-yl]oxyethylamino]but-2-enoate Chemical compound N([C@@H](CC)C=1C=CC=CC=1)C(=O)C(C1=CC=CC=C1N=1)=C(OCCNC(=O)\C=C\C(=O)OC)C=1C1=CC=CC=C1 QRFUDVXZHQAEFC-JSSZYCLJSA-N 0.000 description 1
- GNBWUEAMCSHHMO-UHFFFAOYSA-N methyl 2-carbonochloridoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(Cl)=O GNBWUEAMCSHHMO-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
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- 229940073584 methylene chloride Drugs 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical class C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
- 238000011197 physicochemical method Methods 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- LEWDKQKVAFOMPI-UHFFFAOYSA-N quinoline-4-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CC=NC2=C1 LEWDKQKVAFOMPI-UHFFFAOYSA-N 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
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- 235000009566 rice Nutrition 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 108010016070 senktide Proteins 0.000 description 1
- 230000020341 sensory perception of pain Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 230000000392 somatic effect Effects 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 210000005070 sphincter Anatomy 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 239000002278 tabletting lubricant Substances 0.000 description 1
- 108060008037 tachykinin Proteins 0.000 description 1
- 239000002466 tachykinin receptor agonist Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
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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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
- C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Pulmonology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI952461 IT1276170B1 (it) | 1995-11-24 | 1995-11-24 | Derivati chinolinici |
| ITMI961689 IT1307331B1 (it) | 1996-08-02 | 1996-08-02 | Derivati chinolinici |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA11010A true OA11010A (en) | 2003-03-06 |
Family
ID=26331326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA9800061A OA11010A (en) | 1995-11-24 | 1998-05-22 | Quinoline derivatives |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US6277862B1 (OSRAM) |
| EP (1) | EP0876347B1 (OSRAM) |
| JP (1) | JP2000501104A (OSRAM) |
| KR (1) | KR19990071597A (OSRAM) |
| CN (1) | CN1207730A (OSRAM) |
| AP (1) | AP9801237A0 (OSRAM) |
| AR (1) | AR004972A1 (OSRAM) |
| AT (1) | ATE289994T1 (OSRAM) |
| BG (1) | BG102558A (OSRAM) |
| BR (1) | BR9611820A (OSRAM) |
| CA (1) | CA2238298A1 (OSRAM) |
| CZ (1) | CZ157998A3 (OSRAM) |
| DE (1) | DE69634416T2 (OSRAM) |
| EA (1) | EA002124B1 (OSRAM) |
| ES (1) | ES2236757T3 (OSRAM) |
| IL (1) | IL124522A0 (OSRAM) |
| MX (1) | MX9804107A (OSRAM) |
| NO (1) | NO311212B1 (OSRAM) |
| NZ (1) | NZ323387A (OSRAM) |
| OA (1) | OA11010A (OSRAM) |
| PL (1) | PL326967A1 (OSRAM) |
| SK (1) | SK66798A3 (OSRAM) |
| TR (1) | TR199800924T2 (OSRAM) |
| TW (1) | TW353066B (OSRAM) |
| UY (1) | UY24733A1 (OSRAM) |
| WO (1) | WO1997021680A1 (OSRAM) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993007751A1 (en) * | 1991-10-18 | 1993-04-29 | Monsanto Company | Fungicides for the control of take-all disease of plants |
| SE9703407D0 (sv) * | 1997-09-19 | 1997-09-19 | Astra Ab | New use |
| SE9802073D0 (sv) | 1998-06-11 | 1998-06-11 | Astra Ab | New use |
| GB9825554D0 (en) * | 1998-11-20 | 1999-01-13 | Smithkline Beecham Spa | Novel Compounds |
| US7037922B1 (en) * | 2000-03-10 | 2006-05-02 | Neurogen Corporation | Aryl fused 2,4-disubstituted pyridines: NK3 receptor ligands |
| AU4038600A (en) | 1999-03-29 | 2000-10-16 | Neurogen Corporation | 4-substituted quinoline derivatives as nk-3 and/or gaba(a) receptor ligands |
| WO2000064877A1 (en) | 1999-04-26 | 2000-11-02 | Neurogen Corporation | 2-aminoquinolinecarboxamides: neurokinin receptor ligands |
| WO2002083663A1 (en) * | 2001-04-11 | 2002-10-24 | Glaxosmithkline S.P.A. | Quinoline-4-carboxamide derivatives as nk-3 and nk-2 receptor antagonists |
| AU2002259147A1 (en) * | 2001-05-08 | 2002-11-18 | Schering Corporation | Use of neurokinin receptor antagonists to treat androgen-dependent diseases |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| ATE365174T1 (de) | 2003-01-28 | 2007-07-15 | Microbia Inc | Zusammensetzungen zur behandlung von gastrointestinalen störungen |
| GB0303086D0 (en) | 2003-02-11 | 2003-03-19 | Merck Sharp & Dohme | New compounds |
| GB0419192D0 (en) | 2004-08-27 | 2004-09-29 | Merck Sharp & Dohme | Therapeutic agents |
| BRPI0517567A (pt) * | 2004-11-09 | 2008-06-17 | Smithkline Beecham Corp | composto ou um sal, solvato, ou derivado fisiologicamente funcional farmaceuticamente aceitável do mesmo, composição farmacêutica, usos de um composto ou um sal, solvato, ou derivado fisiologicamente funcional farmaceuticamente aceitável do mesmo e de uma composição farmacêutica, e, processo para preparar um composto |
| GB0425077D0 (en) * | 2004-11-12 | 2004-12-15 | Smithkline Beecham Corp | Novel compounds |
| GB0515580D0 (en) | 2005-07-29 | 2005-09-07 | Merck Sharp & Dohme | Therapeutic compounds |
| JP2009504641A (ja) * | 2005-08-11 | 2009-02-05 | アストラゼネカ・アクチエボラーグ | Ｎｋ−３受容体の調節剤としてのアルキルピリジルキノリン |
| AR057130A1 (es) | 2005-09-21 | 2007-11-14 | Astrazeneca Ab | Quinolinas de alquilsulfoxido y una composicion farmaceutica |
| TW201018662A (en) * | 2005-12-12 | 2010-05-16 | Astrazeneca Ab | Alkylsulphonamide quinolines |
| 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 |
| CN103601792B (zh) | 2007-06-04 | 2016-06-29 | 协同医药品公司 | 有效用于胃肠功能紊乱、炎症、癌症和其他疾病治疗的鸟苷酸环化酶激动剂 |
| BRPI0817721A2 (pt) * | 2007-09-28 | 2015-03-31 | Glaxosmithkline Llc | Composto, composição farmacêutica, método de tratamento, e, processo para preparação de um composto |
| BRPI0817445A2 (pt) * | 2007-09-28 | 2015-10-27 | Glaxosmithkline Llc | composto, composição farmacêutica, método de tratamento, e, processo para preparar um composto |
| AU2009256157B2 (en) | 2008-06-04 | 2014-12-18 | Bausch Health Ireland Limited | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| ES2624828T3 (es) | 2008-07-16 | 2017-07-17 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros |
| WO2018129556A1 (en) | 2017-01-09 | 2018-07-12 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| EP2384318B1 (en) | 2008-12-31 | 2017-11-15 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| HK1211469A1 (en) | 2012-08-21 | 2016-05-27 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| US10376481B2 (en) | 2012-08-21 | 2019-08-13 | Ardelyx, Inc. | Compounds and methods for inhibiting NHE-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| WO2014151206A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| US9486494B2 (en) | 2013-03-15 | 2016-11-08 | Synergy Pharmaceuticals, Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| NZ752535A (en) | 2013-04-12 | 2022-08-26 | Ardelyx Inc | Nhe3-binding compounds and methods for inhibiting phosphate transport |
| WO2014170648A1 (en) | 2013-04-19 | 2014-10-23 | Astrazeneca Ab | A nk3 receptor antagonist compound (nk3ra) for use in a method for the treatment of polycystic ovary syndrome (pcos) |
| EP4424697A3 (en) | 2013-06-05 | 2024-12-25 | Bausch Health Ireland Limited | Ultra-pure agonists of guanylate cyclase c, method of making and using same |
| WO2017072629A1 (en) | 2015-10-29 | 2017-05-04 | Cadila Healthcare Limited | Pharmaceutical combination of nk3 receptor antagonist and biguanides |
| WO2018129552A1 (en) | 2017-01-09 | 2018-07-12 | Ardelyx, Inc. | Compounds useful for treating gastrointestinal tract disorders |
| WO2018129557A1 (en) | 2017-01-09 | 2018-07-12 | Ardelyx, Inc. | Inhibitors of nhe-mediated antiport |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2538388B1 (fr) * | 1982-12-24 | 1985-06-21 | Pharmuka Lab | Nouveaux derives de naphtalene- ou azanaphtalenecarboxamide, leurs procedes de preparation et leur utilisation comme medicaments |
| JPS6399057A (ja) * | 1986-06-27 | 1988-04-30 | Nippon Shinyaku Co Ltd | グリシン誘導体 |
| DE69533408T2 (de) * | 1994-05-27 | 2005-09-08 | Glaxosmithkline S.P.A. | Chinolinderivate als Tachykinin NK3 Rezeptor Antagonisten |
| IT1270615B (it) * | 1994-07-14 | 1997-05-07 | Smithkline Beecham Farma | Uso di derivati di chinolina |
-
1996
- 1996-11-22 CZ CZ981579A patent/CZ157998A3/cs unknown
- 1996-11-22 IL IL12452296A patent/IL124522A0/xx unknown
- 1996-11-22 CA CA002238298A patent/CA2238298A1/en not_active Abandoned
- 1996-11-22 AP APAP/P/1998/001237A patent/AP9801237A0/en unknown
- 1996-11-22 AT AT96941023T patent/ATE289994T1/de not_active IP Right Cessation
- 1996-11-22 CN CN96199753A patent/CN1207730A/zh active Pending
- 1996-11-22 EP EP96941023A patent/EP0876347B1/en not_active Expired - Lifetime
- 1996-11-22 EA EA199800477A patent/EA002124B1/ru not_active IP Right Cessation
- 1996-11-22 US US09/077,151 patent/US6277862B1/en not_active Expired - Fee Related
- 1996-11-22 WO PCT/EP1996/005203 patent/WO1997021680A1/en not_active Ceased
- 1996-11-22 NZ NZ323387A patent/NZ323387A/en unknown
- 1996-11-22 DE DE69634416T patent/DE69634416T2/de not_active Expired - Fee Related
- 1996-11-22 KR KR1019980703873A patent/KR19990071597A/ko not_active Withdrawn
- 1996-11-22 SK SK667-98A patent/SK66798A3/sk unknown
- 1996-11-22 PL PL96326967A patent/PL326967A1/xx unknown
- 1996-11-22 ES ES96941023T patent/ES2236757T3/es not_active Expired - Lifetime
- 1996-11-22 BR BR9611820A patent/BR9611820A/pt not_active Application Discontinuation
- 1996-11-22 JP JP9521658A patent/JP2000501104A/ja active Pending
- 1996-11-22 TR TR1998/00924T patent/TR199800924T2/xx unknown
- 1996-11-23 TW TW085114500A patent/TW353066B/zh active
- 1996-11-25 AR ARP960105317A patent/AR004972A1/es not_active Application Discontinuation
-
1997
- 1997-09-30 UY UY24733A patent/UY24733A1/es not_active Application Discontinuation
-
1998
- 1998-05-22 NO NO19982331A patent/NO311212B1/no unknown
- 1998-05-22 OA OA9800061A patent/OA11010A/en unknown
- 1998-05-22 MX MX9804107A patent/MX9804107A/es unknown
- 1998-06-18 BG BG102558A patent/BG102558A/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO982331D0 (no) | 1998-05-22 |
| IL124522A0 (en) | 1998-12-06 |
| UY24733A1 (es) | 2001-08-27 |
| NO982331L (no) | 1998-07-22 |
| CZ157998A3 (cs) | 1998-12-16 |
| DE69634416D1 (de) | 2005-04-07 |
| AR004972A1 (es) | 1999-04-07 |
| WO1997021680A1 (en) | 1997-06-19 |
| US6277862B1 (en) | 2001-08-21 |
| ES2236757T3 (es) | 2005-07-16 |
| ATE289994T1 (de) | 2005-03-15 |
| SK66798A3 (en) | 1999-01-11 |
| EA002124B1 (ru) | 2001-12-24 |
| KR19990071597A (ko) | 1999-09-27 |
| EA199800477A1 (ru) | 1998-12-24 |
| DE69634416T2 (de) | 2005-12-29 |
| PL326967A1 (en) | 1998-11-09 |
| NO311212B1 (no) | 2001-10-29 |
| AP9801237A0 (en) | 1998-06-30 |
| MX9804107A (es) | 1998-09-30 |
| BG102558A (bg) | 1999-03-31 |
| EP0876347B1 (en) | 2005-03-02 |
| TR199800924T2 (xx) | 1998-08-21 |
| TW353066B (en) | 1999-02-21 |
| JP2000501104A (ja) | 2000-02-02 |
| CA2238298A1 (en) | 1997-06-19 |
| BR9611820A (pt) | 1999-07-13 |
| EP0876347A1 (en) | 1998-11-11 |
| NZ323387A (en) | 2000-02-28 |
| CN1207730A (zh) | 1999-02-10 |
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