DE10215316C1 - Chinolin- und Isochinolin-Derivate, ein pharmazeutisches Mittel und ihre Verwendung als Entzündungshemmer - Google Patents
Chinolin- und Isochinolin-Derivate, ein pharmazeutisches Mittel und ihre Verwendung als EntzündungshemmerInfo
- Publication number
- DE10215316C1 DE10215316C1 DE10215316A DE10215316A DE10215316C1 DE 10215316 C1 DE10215316 C1 DE 10215316C1 DE 10215316 A DE10215316 A DE 10215316A DE 10215316 A DE10215316 A DE 10215316A DE 10215316 C1 DE10215316 C1 DE 10215316C1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- group
- alkyl
- quinolin
- trifluoromethyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title claims abstract description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title abstract description 10
- 229940121363 anti-inflammatory agent Drugs 0.000 title abstract description 3
- 239000002260 anti-inflammatory agent Substances 0.000 title abstract description 3
- 239000008177 pharmaceutical agent Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[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
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- -1 2,5-disubstituted phenyl Chemical class 0.000 description 63
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 55
- 238000004587 chromatography analysis Methods 0.000 description 32
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
- 239000000741 silica gel Substances 0.000 description 30
- 229910002027 silica gel Inorganic materials 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 238000000034 method Methods 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- IDWZSGZOZKRJQF-UHFFFAOYSA-N 4-(1,3-benzodioxol-4-yl)-2-hydroxy-4-methyl-n-quinolin-5-yl-2-(trifluoromethyl)pentanamide Chemical compound C=1C=CC2=NC=CC=C2C=1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=CC2=C1OCO2 IDWZSGZOZKRJQF-UHFFFAOYSA-N 0.000 description 20
- 230000002757 inflammatory effect Effects 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 208000010668 atopic eczema Diseases 0.000 description 17
- 230000008569 process Effects 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 230000000172 allergic effect Effects 0.000 description 16
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 15
- 230000002062 proliferating effect Effects 0.000 description 15
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 201000010099 disease Diseases 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000011734 sodium Substances 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 9
- 239000003862 glucocorticoid Substances 0.000 description 9
- VNWUDLTYIICXJQ-UHFFFAOYSA-N 4-(1,3-benzodioxol-4-yl)-4-methyl-2-oxo-n-quinolin-5-ylpentanamide Chemical compound C=1C=CC2=NC=CC=C2C=1NC(=O)C(=O)CC(C)(C)C1=CC=CC2=C1OCO2 VNWUDLTYIICXJQ-UHFFFAOYSA-N 0.000 description 8
- 102000003676 Glucocorticoid Receptors Human genes 0.000 description 8
- 108090000079 Glucocorticoid Receptors Proteins 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 229940037128 systemic glucocorticoids Drugs 0.000 description 8
- 230000003110 anti-inflammatory effect Effects 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
- 238000002560 therapeutic procedure Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 102000016540 Tyrosine aminotransferases Human genes 0.000 description 5
- 108010042606 Tyrosine transaminase Proteins 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- XMIAFAKRAAMSGX-UHFFFAOYSA-N quinolin-5-amine Chemical compound C1=CC=C2C(N)=CC=CC2=N1 XMIAFAKRAAMSGX-UHFFFAOYSA-N 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 208000026872 Addison Disease Diseases 0.000 description 4
- 206010010356 Congenital anomaly Diseases 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 150000002537 isoquinolines Chemical class 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- 239000002674 ointment Substances 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 102000003998 progesterone receptors Human genes 0.000 description 4
- 108090000468 progesterone receptors Proteins 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 150000004799 α-ketoamides Chemical class 0.000 description 4
- WMYGREUGJWKECP-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(quinolin-4-ylamino)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CNC1=CC=NC2=CC=CC=C12 WMYGREUGJWKECP-UHFFFAOYSA-N 0.000 description 3
- BDZYLNZLEGRWAZ-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(quinolin-5-ylamino)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CNC1=CC=CC2=NC=CC=C12 BDZYLNZLEGRWAZ-UHFFFAOYSA-N 0.000 description 3
- RIJBHAXATUPJIY-UHFFFAOYSA-N 2-[2-(5-fluoro-2-methoxyphenyl)-2-methylpropyl]-2-(trifluoromethyl)oxirane Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC1(C(F)(F)F)OC1 RIJBHAXATUPJIY-UHFFFAOYSA-N 0.000 description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
- IYLAEBLVXYDTHX-UHFFFAOYSA-N 4-(1,3-benzodioxol-4-yl)-4-methyl-2-oxopentanoic acid Chemical compound OC(=O)C(=O)CC(C)(C)C1=CC=CC2=C1OCO2 IYLAEBLVXYDTHX-UHFFFAOYSA-N 0.000 description 3
- YMSHAISWRRFXCM-UHFFFAOYSA-N 4-(5-bromo-2-methoxyphenyl)-4-methyl-2-oxo-n-quinolin-5-ylpentanamide Chemical compound COC1=CC=C(Br)C=C1C(C)(C)CC(=O)C(=O)NC1=CC=CC2=NC=CC=C12 YMSHAISWRRFXCM-UHFFFAOYSA-N 0.000 description 3
- QUKYTYPIHOEBST-UHFFFAOYSA-N 4-(5-bromo-2-methoxyphenyl)-4-methyl-2-oxopentanoic acid Chemical compound COC1=CC=C(Br)C=C1C(C)(C)CC(=O)C(O)=O QUKYTYPIHOEBST-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- 206010002199 Anaphylactic shock Diseases 0.000 description 3
- 102100032187 Androgen receptor Human genes 0.000 description 3
- 206010020751 Hypersensitivity Diseases 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 208000003455 anaphylaxis Diseases 0.000 description 3
- 108010080146 androgen receptors Proteins 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 3
- LKAQUVDGPXTMDG-UHFFFAOYSA-N ethyl 4-(5-bromo-2-methoxyphenyl)-4-methyl-2-oxopentanoate Chemical compound CCOC(=O)C(=O)CC(C)(C)C1=CC(Br)=CC=C1OC LKAQUVDGPXTMDG-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- OSILBMSORKFRTB-UHFFFAOYSA-N isoquinolin-1-amine Chemical compound C1=CC=C2C(N)=NC=CC2=C1 OSILBMSORKFRTB-UHFFFAOYSA-N 0.000 description 3
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical group C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 102000005969 steroid hormone receptors Human genes 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 2
- GXIPDOJMXCLLNI-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-2-[(isoquinolin-1-ylamino)methyl]-4-methylpentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CNC1=NC=CC2=CC=CC=C12 GXIPDOJMXCLLNI-UHFFFAOYSA-N 0.000 description 2
- YAMYQHKLNOXLQB-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(quinolin-8-ylamino)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CNC1=CC=CC2=CC=CN=C12 YAMYQHKLNOXLQB-UHFFFAOYSA-N 0.000 description 2
- GLDQAMYCGOIJDV-UHFFFAOYSA-N 2,3-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1O GLDQAMYCGOIJDV-UHFFFAOYSA-N 0.000 description 2
- GWSAMFZWJRKRTR-UHFFFAOYSA-N 2-(2-methyl-2-phenylpropyl)-2-(trifluoromethyl)oxirane Chemical compound C=1C=CC=CC=1C(C)(C)CC1(C(F)(F)F)CO1 GWSAMFZWJRKRTR-UHFFFAOYSA-N 0.000 description 2
- PWTRJTSMRTULMY-UHFFFAOYSA-N 2-(5-bromo-2-methoxyphenyl)propan-2-ol Chemical compound COC1=CC=C(Br)C=C1C(C)(C)O PWTRJTSMRTULMY-UHFFFAOYSA-N 0.000 description 2
- OESCYAPQFSNTHU-UHFFFAOYSA-N 4-(2-chloro-5-fluorophenyl)-4-methyl-2-oxo-n-quinolin-5-ylpentanamide Chemical compound C=1C=CC2=NC=CC=C2C=1NC(=O)C(=O)CC(C)(C)C1=CC(F)=CC=C1Cl OESCYAPQFSNTHU-UHFFFAOYSA-N 0.000 description 2
- PDICOYPBPNVGDZ-UHFFFAOYSA-N 4-(2-chlorophenyl)-4-methyl-2-oxo-n-quinolin-5-ylpentanamide Chemical compound C=1C=CC2=NC=CC=C2C=1NC(=O)C(=O)CC(C)(C)C1=CC=CC=C1Cl PDICOYPBPNVGDZ-UHFFFAOYSA-N 0.000 description 2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 2
- USLKCMBGQFYUFI-UHFFFAOYSA-N dichloromethane;tribromoborane Chemical compound ClCCl.BrB(Br)Br USLKCMBGQFYUFI-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
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- KRPFJCUXHWEVMS-UHFFFAOYSA-N methyl 1,3-benzodioxole-4-carboxylate Chemical compound COC(=O)C1=CC=CC2=C1OCO2 KRPFJCUXHWEVMS-UHFFFAOYSA-N 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
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- 229940124597 therapeutic agent Drugs 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
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- 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
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Landscapes
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Priority Applications (37)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10215316A DE10215316C1 (de) | 2002-04-02 | 2002-04-02 | Chinolin- und Isochinolin-Derivate, ein pharmazeutisches Mittel und ihre Verwendung als Entzündungshemmer |
| CN038126842A CN1659144B (zh) | 2002-04-02 | 2003-03-29 | 喹啉和异喹啉衍生物、其制备方法以及作为炎症抑制剂的应用 |
| AT03745195T ATE355277T1 (de) | 2002-04-02 | 2003-03-29 | Chinolin- und isochinolin-derivate, ein verfahren zu ihrer herstellung und ihre verwendung als entzündungshemmer |
| KR1020047015697A KR100967277B1 (ko) | 2002-04-02 | 2003-03-29 | 퀴놀린 및 이소퀴놀린 유도체, 그의 제조 방법 및항염증제로서의 그의 용도 |
| NZ535872A NZ535872A (en) | 2002-04-02 | 2003-03-29 | Quinoline and isoquinoline derivatives, a process for their production and their use as inflammation inhibitors |
| CA2481012A CA2481012C (en) | 2002-04-02 | 2003-03-29 | Quinoline and isoquinoline derivatives, a process for their production and their use as inflammation inhibitors |
| BR0308967-3A BR0308967A (pt) | 2002-04-02 | 2003-03-29 | Derivados de quinolina e isoquinolina, um processo para a sua preparação e sua aplicação como inibidores de inflamação |
| MEP-142/08A MEP14208A (en) | 2002-04-02 | 2003-03-29 | Quinoline and isoquinoline derivatives, method for the production thereof and use thereof as anti-inflammatory agents |
| MEP-2008-142A ME00159B (me) | 2002-04-02 | 2003-03-29 | DERIVATI HINOLINA l IZOHINOLINA, POSTUPAK ZA NJIHOVO DOBIJANJE l NJIHOVA PRIMENA KAO SUPRESORA ZAPALJENJA |
| MXPA04009684A MXPA04009684A (es) | 2002-04-02 | 2003-03-29 | Derivados de quinolina e isoquinolina, metodo para su produccion y su uso como inhibidores de inflamaciones. |
| DE50306659T DE50306659D1 (de) | 2002-04-02 | 2003-03-29 | Chinolin- und isochinolin-derivate, ein verfahren zu ihrer herstellung und ihre verwendung als entzündungshemmer |
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| JP2023519585A (ja) | 2020-03-26 | 2023-05-11 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッド | ウイルス感染を予防または治療するカテプシン阻害剤 |
| CN113480512B (zh) * | 2021-07-23 | 2022-07-29 | 阜阳欣奕华制药科技有限公司 | 一种1-(7-溴苯并并[d][1,3]二氧杂环戊烯-4-基)乙-1-酮的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2002010143A1 (de) * | 2000-07-28 | 2002-02-07 | Schering Aktiengesellschaft | Nichtsteroidale entzündungshemmer |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB8617653D0 (en) * | 1986-07-18 | 1986-08-28 | Ici Plc | Amide derivatives |
| DE19723722A1 (de) * | 1997-05-30 | 1998-12-10 | Schering Ag | Nichtsteroidale Gestagene |
| DE19856475A1 (de) * | 1998-11-27 | 2000-05-31 | Schering Ag | Nichtsteroidale Entzündungshemmer |
| US6897224B2 (en) * | 2002-04-02 | 2005-05-24 | Schering Ag | Quinoline and isoquinoline derivatives, a process for their production and their use as inflammation inhibitors |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002010143A1 (de) * | 2000-07-28 | 2002-02-07 | Schering Aktiengesellschaft | Nichtsteroidale entzündungshemmer |
| DE10038639A1 (de) * | 2000-07-28 | 2002-02-21 | Schering Ag | Nichtsteroidale Entzündungshemmer |
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