KR20030027016A - 항-염증제로서의 퀴놀린 유도체 - Google Patents
항-염증제로서의 퀴놀린 유도체 Download PDFInfo
- Publication number
- KR20030027016A KR20030027016A KR10-2003-7001942A KR20037001942A KR20030027016A KR 20030027016 A KR20030027016 A KR 20030027016A KR 20037001942 A KR20037001942 A KR 20037001942A KR 20030027016 A KR20030027016 A KR 20030027016A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- compound
- alkyl
- methoxy
- methanesulfonyl
- Prior art date
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- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title abstract description 3
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title abstract 2
- 239000002260 anti-inflammatory agent Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 160
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 25
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- -1 4-substituted phenyl Chemical group 0.000 claims description 160
- 125000000217 alkyl group Chemical group 0.000 claims description 89
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 65
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 19
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 15
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- 239000003814 drug Substances 0.000 claims description 14
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 8
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- 125000003342 alkenyl group Chemical group 0.000 claims description 6
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- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
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- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 5
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- KIWSYRHAAPLJFJ-DNZSEPECSA-N n-[(e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enyl]pyridine-3-carboxamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/CNC(=O)C1=CC=CN=C1 KIWSYRHAAPLJFJ-DNZSEPECSA-N 0.000 claims description 3
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
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- 208000023275 Autoimmune disease Diseases 0.000 abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 56
- 239000000243 solution Substances 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 235000019439 ethyl acetate Nutrition 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
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- 108010037462 Cyclooxygenase 2 Proteins 0.000 description 22
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 21
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- 239000000460 chlorine Substances 0.000 description 20
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 12
- 230000003110 anti-inflammatory effect Effects 0.000 description 11
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- 150000003180 prostaglandins Chemical class 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- OFUFXTHGZWIDDB-UHFFFAOYSA-N 2-chloroquinoline Chemical compound C1=CC=CC2=NC(Cl)=CC=C21 OFUFXTHGZWIDDB-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 239000004215 Carbon black (E152) Substances 0.000 description 8
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- 125000003884 phenylalkyl group Chemical group 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 7
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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- AREWYRAETFMKAH-UHFFFAOYSA-N 1-sulfidoquinolin-1-ium Chemical compound C1=CC=C2[N+]([S-])=CC=CC2=C1 AREWYRAETFMKAH-UHFFFAOYSA-N 0.000 description 5
- WPLABWLKEPFOSQ-UHFFFAOYSA-N 5-(2,4-difluorophenyl)sulfanyl-6-methoxy-2-methylsulfonylquinoline Chemical compound COC1=CC=C2N=C(S(C)(=O)=O)C=CC2=C1SC1=CC=C(F)C=C1F WPLABWLKEPFOSQ-UHFFFAOYSA-N 0.000 description 5
- OIYRFJFOTTZCJL-UHFFFAOYSA-N 5-(4-fluorophenyl)sulfanyl-2-methylsulfonylquinolin-6-ol Chemical compound OC=1C=CC2=NC(S(=O)(=O)C)=CC=C2C=1SC1=CC=C(F)C=C1 OIYRFJFOTTZCJL-UHFFFAOYSA-N 0.000 description 5
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Classifications
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- 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
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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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- 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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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Pregnancy & Childbirth (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Immunology (AREA)
- Gynecology & Obstetrics (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22419600P | 2000-08-09 | 2000-08-09 | |
| US60/224,196 | 2000-08-09 | ||
| PCT/EP2001/008880 WO2002012192A1 (en) | 2000-08-09 | 2001-08-01 | Quinolene derivatives as anti-inflammation agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20030027016A true KR20030027016A (ko) | 2003-04-03 |
Family
ID=22839655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR10-2003-7001942A Ceased KR20030027016A (ko) | 2000-08-09 | 2001-08-01 | 항-염증제로서의 퀴놀린 유도체 |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US7049325B2 (https=) |
| EP (1) | EP1313707B1 (https=) |
| JP (1) | JP3930428B2 (https=) |
| KR (1) | KR20030027016A (https=) |
| CN (1) | CN1199950C (https=) |
| AR (1) | AR033554A1 (https=) |
| AT (1) | ATE367379T1 (https=) |
| AU (1) | AU2001277560A1 (https=) |
| BR (1) | BR0113175A (https=) |
| CA (1) | CA2418832A1 (https=) |
| DE (1) | DE60129445T2 (https=) |
| ES (1) | ES2290161T3 (https=) |
| MX (1) | MXPA03001178A (https=) |
| WO (1) | WO2002012192A1 (https=) |
| ZA (1) | ZA200300847B (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW591089B (en) * | 2001-08-09 | 2004-06-11 | Cheil Ind Inc | Slurry composition for use in chemical mechanical polishing of metal wiring |
| GB0220953D0 (en) * | 2002-09-10 | 2002-10-23 | Novartis Ag | Organic compounds |
| US7132432B2 (en) * | 2003-06-05 | 2006-11-07 | Bristol-Myers Squibb Company | Hydantoin derivatives as inhibitors of tumor necrosis factor-alpha converting enzyme (TACE) |
| AU2006220708B9 (en) * | 2005-03-08 | 2013-01-17 | Boehringer Ingelheim International Gmbh | Process for preparing macrocyclic compounds |
| PE20110343A1 (es) * | 2008-09-17 | 2011-06-25 | Boehringer Ingelheim Int | Combinacion de inhibidor de la proteasa ns3 de hcv con interferon y ribavirina |
| EA201200650A1 (ru) | 2009-10-30 | 2012-12-28 | Бёрингер Ингельхайм Интернациональ Гмбх | Курсы комбинированного лечения вируса гепатита с, включающие bi201335, интерферон-альфа и рибавирин |
| US9383448B2 (en) | 2012-07-05 | 2016-07-05 | Deca System Co., Ltd. | Golf GPS device with automatic hole recognition and playing hole selection |
| CN117924243B (zh) * | 2024-01-16 | 2025-09-12 | 沈阳药科大学 | 一种喹啉衍生物及其药用组合物和应用 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9018134D0 (en) | 1989-09-29 | 1990-10-03 | Ici Plc | Heterocyclic derivatives |
| MX9200299A (es) | 1991-02-07 | 1992-12-01 | Roussel Uclaf | Nuevos derivados biciclicos nitrogenados, su procedimiento de preparacion los nuevos compuestos intermedios obtenidos su aplicacion como medicamentos y las composiciones farmaceuticas que los contienen. |
| EP0498722B1 (fr) | 1991-02-07 | 1997-07-30 | Roussel Uclaf | Dérivés bicycliques azotés, leur procédé de préparation, les intermédiaires obtenus, leur application comme médicaments et les compositions pharmaceutiques les renfermant |
| GB9311790D0 (en) * | 1993-06-08 | 1993-07-28 | Minnesota Mining & Mfg | Photothermographic materials |
| DK122693D0 (da) | 1993-10-29 | 1993-10-29 | Hempels Skibsfarve Fab J C | Marin struktur |
| AU715358B2 (en) * | 1995-04-28 | 2000-01-20 | Takeda Chemical Industries Ltd. | Therapeutic composition for arthritis |
| DE19638484A1 (de) * | 1996-09-20 | 1998-03-26 | Basf Ag | Hetaroylderivate |
| DE19638486A1 (de) * | 1996-09-20 | 1998-03-26 | Basf Ag | Hetaroylderivate |
| US6069151A (en) | 1996-11-06 | 2000-05-30 | Darwin Discovery, Ltd. | Quinolines and their therapeutic use |
| PA8444901A1 (es) | 1997-01-28 | 2000-05-24 | Hoffmann La Roche | Derivados de 5-aroilnaftaleno como agentes anti-inflamatorios |
| US6077850A (en) * | 1997-04-21 | 2000-06-20 | G.D. Searle & Co. | Substituted benzopyran analogs for the treatment of inflammation |
| US6034256A (en) | 1997-04-21 | 2000-03-07 | G.D. Searle & Co. | Substituted benzopyran derivatives for the treatment of inflammation |
| US6479438B2 (en) * | 2001-01-04 | 2002-11-12 | Isp Investments Inc. | Gel inhibited liquid carrier for a biocide containing a carbodiimide and an emulsifier mixture |
-
2001
- 2001-08-01 EP EP01955382A patent/EP1313707B1/en not_active Expired - Lifetime
- 2001-08-01 CN CNB018163513A patent/CN1199950C/zh not_active Expired - Fee Related
- 2001-08-01 KR KR10-2003-7001942A patent/KR20030027016A/ko not_active Ceased
- 2001-08-01 ES ES01955382T patent/ES2290161T3/es not_active Expired - Lifetime
- 2001-08-01 JP JP2002518170A patent/JP3930428B2/ja not_active Expired - Fee Related
- 2001-08-01 DE DE60129445T patent/DE60129445T2/de not_active Expired - Fee Related
- 2001-08-01 MX MXPA03001178A patent/MXPA03001178A/es unknown
- 2001-08-01 AT AT01955382T patent/ATE367379T1/de not_active IP Right Cessation
- 2001-08-01 AU AU2001277560A patent/AU2001277560A1/en not_active Abandoned
- 2001-08-01 WO PCT/EP2001/008880 patent/WO2002012192A1/en not_active Ceased
- 2001-08-01 BR BR0113175-3A patent/BR0113175A/pt not_active IP Right Cessation
- 2001-08-01 CA CA002418832A patent/CA2418832A1/en not_active Abandoned
- 2001-08-07 US US09/925,883 patent/US7049325B2/en not_active Expired - Fee Related
- 2001-08-08 AR ARP010103784A patent/AR033554A1/es not_active Application Discontinuation
-
2003
- 2003-01-30 ZA ZA200300847A patent/ZA200300847B/en unknown
-
2005
- 2005-11-30 US US11/291,867 patent/US7186840B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200300847B (en) | 2004-04-30 |
| DE60129445T2 (de) | 2008-04-24 |
| EP1313707A1 (en) | 2003-05-28 |
| EP1313707B1 (en) | 2007-07-18 |
| US7049325B2 (en) | 2006-05-23 |
| US20060084677A1 (en) | 2006-04-20 |
| JP3930428B2 (ja) | 2007-06-13 |
| US7186840B2 (en) | 2007-03-06 |
| MXPA03001178A (es) | 2003-06-30 |
| US20020082276A1 (en) | 2002-06-27 |
| ATE367379T1 (de) | 2007-08-15 |
| AR033554A1 (es) | 2003-12-26 |
| JP2004505951A (ja) | 2004-02-26 |
| CN1199950C (zh) | 2005-05-04 |
| WO2002012192A1 (en) | 2002-02-14 |
| AU2001277560A1 (en) | 2002-02-18 |
| ES2290161T3 (es) | 2008-02-16 |
| BR0113175A (pt) | 2004-02-17 |
| CA2418832A1 (en) | 2002-02-14 |
| CN1466575A (zh) | 2004-01-07 |
| DE60129445D1 (de) | 2007-08-30 |
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