OA11010A - Quinoline derivatives - Google Patents

Quinoline derivatives Download PDF

Info

Publication number: OA11010A
Authority: OA; OAPI
Prior art keywords: compound; formula; alkyl; group; mmol
Prior art date: 1995-11-24

Application number

OA9800061A

Other languages

English (en)

Inventor

Giuseppe Amaldo Maria

Mario Grugni

Luca Francesco Raeglia

Carlo Farina

Original Assignee

Smithkline Beecham Spa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1995-11-24

Filing date

1998-05-22

Publication date

2003-03-06

1995-11-24 Priority claimed from ITMI952461 external-priority patent/IT1276170B1/it

1996-08-02 Priority claimed from IT96MI001689 external-priority patent/IT1307331B1/it

1998-05-22 Application filed by Smithkline Beecham Spa filed Critical Smithkline Beecham Spa

2003-03-06 Publication of OA11010A publication Critical patent/OA11010A/en

Links

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
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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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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
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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
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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
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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
235000015320 potassium carbonate Nutrition 0.000 description 7
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238000005160 1H NMR spectroscopy Methods 0.000 description 6
101001125071 Homo sapiens Neuromedin-K receptor Proteins 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
239000007788 liquid Substances 0.000 description 6
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
239000002253 acid Substances 0.000 description 5
239000003921 oil Substances 0.000 description 5
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239000000047 product Substances 0.000 description 5
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
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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
102100029409 Neuromedin-K receptor Human genes 0.000 description 4
230000036428 airway hyperreactivity Effects 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
230000003197 catalytic effect Effects 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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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
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MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical compound C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 description 3
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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
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
229940073584 methylene chloride Drugs 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
201000006417 multiple sclerosis Diseases 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229920003052 natural elastomer Polymers 0.000 description 1
229920001194 natural rubber Polymers 0.000 description 1
208000004296 neuralgia Diseases 0.000 description 1
208000015122 neurodegenerative disease Diseases 0.000 description 1
239000002687 nonaqueous vehicle Substances 0.000 description 1
229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
238000005192 partition Methods 0.000 description 1
230000037361 pathway Effects 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
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
206010039083 rhinitis Diseases 0.000 description 1
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
230000002455 vasospastic effect Effects 0.000 description 1
239000003981 vehicle 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
- C07D215/48—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)

OA9800061A 1995-11-24 1998-05-22 Quinoline derivatives OA11010A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
ITMI952461 IT1276170B1 (it)	1995-11-24	1995-11-24	Derivati chinolinici
IT96MI001689 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 (fr)
EP (1)	EP0876347B1 (fr)
JP (1)	JP2000501104A (fr)
KR (1)	KR19990071597A (fr)
CN (1)	CN1207730A (fr)
AP (1)	AP9801237A0 (fr)
AR (1)	AR004972A1 (fr)
AT (1)	ATE289994T1 (fr)
BG (1)	BG102558A (fr)
BR (1)	BR9611820A (fr)
CA (1)	CA2238298A1 (fr)
CZ (1)	CZ157998A3 (fr)
DE (1)	DE69634416T2 (fr)
EA (1)	EA002124B1 (fr)
ES (1)	ES2236757T3 (fr)
IL (1)	IL124522A0 (fr)
MX (1)	MX9804107A (fr)
NO (1)	NO311212B1 (fr)
NZ (1)	NZ323387A (fr)
OA (1)	OA11010A (fr)
PL (1)	PL326967A1 (fr)
SK (1)	SK66798A3 (fr)
TR (1)	TR199800924T2 (fr)
TW (1)	TW353066B (fr)
UY (1)	UY24733A1 (fr)
WO (1)	WO1997021680A1 (fr)

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SE9703407D0 (sv) *	1997-09-19	1997-09-19	Astra Ab	New use
SE9802073D0 (sv)	1998-06-11	1998-06-11	Astra Ab	New use
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US7037922B1 (en)	2000-03-10	2006-05-02	Neurogen Corporation	Aryl fused 2,4-disubstituted pyridines: NK3 receptor ligands
ATE247652T1 (de)	1999-03-29	2003-09-15	Neurogen Corp	4-substituierte chinolinderivate als nk-3 und/oder gaba(a) rezeptor liganden
WO2000064877A1 (fr) *	1999-04-26	2000-11-02	Neurogen Corporation	2-aminoquinolinecarboxamides: ligands de recepteurs de la neurokinine
EP1385839B1 (fr) *	2001-04-11	2006-02-22	GlaxoSmithKline S.p.A.	Derives de 3-substitue quinoline-4-carboxamide utilises comme antagonistes du recepteur nk3 et du recepteur nk2
WO2002089802A2 (fr) *	2001-05-08	2002-11-14	Schering Corporation	Utilisation d'antagonistes de recepteur de neurokinine pour le traitement de maladies liees aux androgenes
US7772188B2 (en)	2003-01-28	2010-08-10	Ironwood Pharmaceuticals, Inc.	Methods and compositions for the treatment of gastrointestinal disorders
BR122018074353B8 (pt)	2003-01-28	2023-05-02	Ironwood Pharmaceuticals Inc	composição farmacêutica, polipeptídeo e métodos para a produção dos mesmos
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
WO2006052722A1 (fr) *	2004-11-09	2006-05-18	Smithkline Beecham Corporation	Composes inhibiteurs de la phosphorylase du glycogene et compositions pharmaceutiques les comprenant
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
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TW201018662A (en) *	2005-12-12	2010-05-16	Astrazeneca Ab	Alkylsulphonamide quinolines
WO2008151257A2 (fr)	2007-06-04	2008-12-11	Synergy Pharmaceuticals Inc.	Agonistes de guanylase cyclase utiles pour le traitement de troubles gastro-intestinaux, d'inflammation, de cancer et d'autres troubles
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
US20100305207A1 (en) *	2007-09-28	2010-12-02	Pierette Banker	Glycogen phosphorylase inhibitor compound and pharmaceutical composition thereof
CN101861303A (zh) *	2007-09-28	2010-10-13	葛兰素史密丝克莱恩有限责任公司	糖原磷酸化酶抑制剂化合物和其药物组合物
ES2627848T3 (es)	2008-06-04	2017-07-31	Synergy Pharmaceuticals Inc.	Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos
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
CN103819403B (zh)	2008-12-31	2017-01-04	阿德利克斯公司	用于治疗与体液潴留或盐超负荷有关的病症和胃肠道病症的化合物和方法
WO2018129556A1 (fr)	2017-01-09	2018-07-12	Ardelyx, Inc.	Composés et procédés pour l'inhibition d'un antiport à médiation par échangeur sodium/proton (nhe) dans le traitement de troubles associés à une rétention d'eau ou à une surcharge en sel et de troubles du tractus gastro-intestinal
US9616097B2 (en)	2010-09-15	2017-04-11	Synergy Pharmaceuticals, Inc.	Formulations of guanylate cyclase C agonists and methods of use
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
RU2015107019A (ru)	2012-08-21	2016-10-10	Эрделикс Инк.	Соединения и способы для ингибирования nhe-опосредованного антипорта в лечении расстройств, ассоциированных с задержкой жидкости или солевой перегрузкой и заболеваний желудочно-кишечного тракта
EP2968439A2 (fr)	2013-03-15	2016-01-20	Synergy Pharmaceuticals Inc.	Compositions utiles pour le traitement de troubles gastro-intestinaux
US9708367B2 (en)	2013-03-15	2017-07-18	Synergy Pharmaceuticals, Inc.	Agonists of guanylate cyclase and their uses
CN105392483B (zh)	2013-04-12	2019-03-15	阿德利克斯公司	用于抑制磷酸盐转运的nhe3结合化合物和方法
BR112015026519A2 (pt)	2013-04-19	2017-07-25	Astrazeneca Ab	composto antagonista do receptor nk3 (nk3ra) para uso em um método destinado ao tratamento de síndrome do ovário policístico (sop)
PL3004138T3 (pl)	2013-06-05	2024-07-29	Bausch Health Ireland Limited	Ultra-oczyszczeni agoniści peptydowi cyklazy guanylanowej C, sposób ich uzyskiwania i ich zastosowanie
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KR20240090875A (ko)	2017-01-09	2024-06-21	알데릭스, 인코포레이티드	위장관 장애를 치료하는 데 유용한 화합물

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IT1270615B (it) *	1994-07-14	1997-05-07	Smithkline Beecham Farma	Uso di derivati di chinolina

1996
- 1996-11-22 AT AT96941023T patent/ATE289994T1/de 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/fr not_active Ceased
- 1996-11-22 BR BR9611820A patent/BR9611820A/pt not_active Application Discontinuation
- 1996-11-22 NZ NZ323387A patent/NZ323387A/en unknown
- 1996-11-22 CA CA002238298A patent/CA2238298A1/fr not_active Abandoned
- 1996-11-22 IL IL12452296A patent/IL124522A0/xx unknown
- 1996-11-22 EA EA199800477A patent/EA002124B1/ru not_active IP Right Cessation
- 1996-11-22 ES ES96941023T patent/ES2236757T3/es not_active Expired - Lifetime
- 1996-11-22 DE DE69634416T patent/DE69634416T2/de not_active Expired - Fee Related
- 1996-11-22 JP JP9521658A patent/JP2000501104A/ja active Pending
- 1996-11-22 EP EP96941023A patent/EP0876347B1/fr not_active Expired - Lifetime
- 1996-11-22 AP APAP/P/1998/001237A patent/AP9801237A0/en unknown
- 1996-11-22 CN CN96199753A patent/CN1207730A/zh active Pending
- 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 TR TR1998/00924T patent/TR199800924T2/xx unknown
- 1996-11-22 CZ CZ981579A patent/CZ157998A3/cs 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 MX MX9804107A patent/MX9804107A/es unknown
- 1998-05-22 OA OA9800061A patent/OA11010A/en unknown
- 1998-06-18 BG BG102558A patent/BG102558A/bg unknown

Also Published As

Publication number	Publication date
AP9801237A0 (en)	1998-06-30
DE69634416T2 (de)	2005-12-29
JP2000501104A (ja)	2000-02-02
NO311212B1 (no)	2001-10-29
NO982331D0 (no)	1998-05-22
PL326967A1 (en)	1998-11-09
DE69634416D1 (de)	2005-04-07
WO1997021680A1 (fr)	1997-06-19
TR199800924T2 (xx)	1998-08-21
TW353066B (en)	1999-02-21
EA199800477A1 (ru)	1998-12-24
UY24733A1 (es)	2001-08-27
IL124522A0 (en)	1998-12-06
ES2236757T3 (es)	2005-07-16
AR004972A1 (es)	1999-04-07
BG102558A (bg)	1999-03-31
CN1207730A (zh)	1999-02-10
BR9611820A (pt)	1999-07-13
SK66798A3 (en)	1999-01-11
KR19990071597A (ko)	1999-09-27
ATE289994T1 (de)	2005-03-15
NO982331L (no)	1998-07-22
NZ323387A (en)	2000-02-28
MX9804107A (es)	1998-09-30
EP0876347B1 (fr)	2005-03-02
CZ157998A3 (cs)	1998-12-16
EP0876347A1 (fr)	1998-11-11
US6277862B1 (en)	2001-08-21
CA2238298A1 (fr)	1997-06-19
EA002124B1 (ru)	2001-12-24

Publication	Publication Date	Title
US6277862B1 (en)	2001-08-21	Quinoline derivatives
WO1997021680A9 (fr)	1997-09-12	Derives de quinoline
US6743804B2 (en)	2004-06-01	Quinoline derivatives as NK3 antagonists
EP0804419B1 (fr)	2003-08-06	Derives de quinoline utilises comme antagonistes du recepteur nk 3 de la tachykinine
US20020068827A1 (en)	2002-06-06	Quinoline-4-carboxamide derivatives, their preparation and their use as neurokinin 3 ( NK-3 ) - and neurokinin 2 ( NK-3 ) receptor antagonists
WO1996002509A1 (fr)	1996-02-01	Derives de quinoline utilises comme antagonistes de la neurokinine 3 (nk3)
EP1377555B1 (fr)	2007-01-24	Un derive de dioxino[2,3-g]quinoline-9-acide carboxylique en tant qu'antagoniste du recepteur nk3
EP0983262B1 (fr)	2003-07-09	Derives de quinoline-4-carboxamide comme antagonistes des recepteurs nk-2 et nk-3
EP1131294B1 (fr)	2006-12-20	Derives de quinoline utilises comme ligands des recepteurs nk-2 et nk-3
AU1031797A (en)	1997-07-03	Quinoline derivatives
AU757836B2 (en)	2003-03-06	Quinoline derivatives
US20030004183A1 (en)	2003-01-02	Quinoline-4-carboxamide derivatives as NK-2 and NK-3 receptor antagonists
NZ500371A (en)	2001-08-31	NK-2/NK-3 antagonists and their use in treating respiratory disease
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