UA78304C2 - Quinoline and isoquinoline derivatives, use thereof as anti-inflammatory agents and pharmaceutical preparation based thereon - Google Patents
Quinoline and isoquinoline derivatives, use thereof as anti-inflammatory agents and pharmaceutical preparation based thereon Download PDFInfo
- Publication number
- UA78304C2 UA78304C2 UA20041108938A UA20041108938A UA78304C2 UA 78304 C2 UA78304 C2 UA 78304C2 UA 20041108938 A UA20041108938 A UA 20041108938A UA 20041108938 A UA20041108938 A UA 20041108938A UA 78304 C2 UA78304 C2 UA 78304C2
- Authority
- UA
- Ukraine
- Prior art keywords
- group
- methyl
- trifluoromethyl
- mixture
- ethyl acetate
- Prior art date
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- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title claims abstract description 12
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title abstract description 14
- 229940121363 anti-inflammatory agent Drugs 0.000 title abstract 2
- 239000002260 anti-inflammatory agent Substances 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 claims description 236
- 150000001875 compounds Chemical class 0.000 claims description 108
- 239000001257 hydrogen Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229940126601 medicinal product Drugs 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical group OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- AEMOLEFTQBMNLQ-SYJWYVCOSA-N (2s,3s,4s,5s,6r)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid Chemical group O[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H]1O AEMOLEFTQBMNLQ-SYJWYVCOSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 40
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 303
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 143
- 239000000741 silica gel Substances 0.000 description 134
- 229910002027 silica gel Inorganic materials 0.000 description 134
- 239000000047 product Substances 0.000 description 125
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 122
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 119
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 116
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 109
- 239000000243 solution Substances 0.000 description 100
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 84
- 238000004587 chromatography analysis Methods 0.000 description 83
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 71
- 238000005160 1H NMR spectroscopy Methods 0.000 description 70
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 70
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
- -1 2,5-disubstituted phenyl Chemical class 0.000 description 58
- 239000002904 solvent Substances 0.000 description 54
- 238000005481 NMR spectroscopy Methods 0.000 description 50
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 49
- 229910052938 sodium sulfate Inorganic materials 0.000 description 49
- 235000011152 sodium sulphate Nutrition 0.000 description 49
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 46
- 239000012074 organic phase Substances 0.000 description 41
- 238000000746 purification Methods 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- 239000012047 saturated solution Substances 0.000 description 35
- 239000011541 reaction mixture Substances 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 239000003921 oil Substances 0.000 description 30
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 29
- 238000003756 stirring Methods 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 26
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 26
- 229960000583 acetic acid Drugs 0.000 description 25
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 239000012279 sodium borohydride Substances 0.000 description 21
- 229910000033 sodium borohydride Inorganic materials 0.000 description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
- 239000012267 brine Substances 0.000 description 19
- 230000002757 inflammatory effect Effects 0.000 description 19
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 18
- 239000000284 extract Substances 0.000 description 18
- 230000003993 interaction Effects 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- 208000010668 atopic eczema Diseases 0.000 description 17
- APQGIAYQAYOKSU-UHFFFAOYSA-N 5-aminoquinoline-2-carboxylic acid Chemical compound OC(=O)C1=CC=C2C(N)=CC=CC2=N1 APQGIAYQAYOKSU-UHFFFAOYSA-N 0.000 description 16
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 16
- 230000000172 allergic effect Effects 0.000 description 16
- 239000008346 aqueous phase Substances 0.000 description 16
- 201000010099 disease Diseases 0.000 description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 238000012545 processing Methods 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
- 125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 description 15
- 230000008569 process Effects 0.000 description 15
- 230000002062 proliferating effect Effects 0.000 description 15
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 15
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
- 238000001816 cooling Methods 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- HLEKYJVHEBHTMR-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O.CCCCC(N)=O HLEKYJVHEBHTMR-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 11
- 150000001408 amides Chemical class 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000012298 atmosphere Substances 0.000 description 10
- 239000012141 concentrate Substances 0.000 description 10
- VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical compound C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 description 10
- 150000004702 methyl esters Chemical class 0.000 description 10
- 229910052763 palladium Inorganic materials 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000003518 caustics Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 8
- UNSLQFMTPYHZDA-UHFFFAOYSA-N 2-methylquinolin-5-amine Chemical compound NC1=CC=CC2=NC(C)=CC=C21 UNSLQFMTPYHZDA-UHFFFAOYSA-N 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 239000012230 colorless oil Substances 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 230000004054 inflammatory process Effects 0.000 description 7
- XMIAFAKRAAMSGX-UHFFFAOYSA-N quinolin-5-amine Chemical compound C1=CC=C2C(N)=CC=CC2=N1 XMIAFAKRAAMSGX-UHFFFAOYSA-N 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 6
- 238000005119 centrifugation Methods 0.000 description 6
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 6
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 6
- 239000003862 glucocorticoid Substances 0.000 description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- 239000002594 sorbent Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000010936 titanium Substances 0.000 description 6
- 229910052719 titanium Inorganic materials 0.000 description 6
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 6
- IICVTJMDHNPPOP-UHFFFAOYSA-N 2-chloro-5-nitroquinoline Chemical compound ClC1=CC=C2C([N+](=O)[O-])=CC=CC2=N1 IICVTJMDHNPPOP-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 5
- 206010061218 Inflammation Diseases 0.000 description 5
- 102000016540 Tyrosine aminotransferases Human genes 0.000 description 5
- 108010042606 Tyrosine transaminase Proteins 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 5
- 229910000024 caesium carbonate Inorganic materials 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000002274 desiccant Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 5
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 5
- GLDQAMYCGOIJDV-UHFFFAOYSA-N 2,3-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1O GLDQAMYCGOIJDV-UHFFFAOYSA-N 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- 210000004100 adrenal gland Anatomy 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- LSXRQJWRXAOUIA-UHFFFAOYSA-N hexan-3-ol Chemical compound CCCC(O)CC.CCCC(O)CC LSXRQJWRXAOUIA-UHFFFAOYSA-N 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- ZOCHHNOQQHDWHG-UHFFFAOYSA-N n-hexan-3-ol Natural products CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 description 4
- 239000002674 ointment Substances 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- 239000004323 potassium nitrate Substances 0.000 description 4
- 235000010333 potassium nitrate Nutrition 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 230000009885 systemic effect Effects 0.000 description 4
- 229940037128 systemic glucocorticoids Drugs 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 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
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- DBUAYOWCIUQXQW-UHFFFAOYSA-N 1,3-benzodioxole-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1OCO2 DBUAYOWCIUQXQW-UHFFFAOYSA-N 0.000 description 3
- JJPSZKIOGBRMHK-UHFFFAOYSA-N 2,6-dimethylquinoline Chemical compound N1=C(C)C=CC2=CC(C)=CC=C21 JJPSZKIOGBRMHK-UHFFFAOYSA-N 0.000 description 3
- YNXOMDRPWQMDQL-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-methylpropanal Chemical compound O=CC(C)(C)C1=CC=C(Cl)C=C1 YNXOMDRPWQMDQL-UHFFFAOYSA-N 0.000 description 3
- JYYDVCMSWBKAIJ-UHFFFAOYSA-N 2-ethenyl-5-nitroquinoline Chemical compound C=CC1=CC=C2C([N+](=O)[O-])=CC=CC2=N1 JYYDVCMSWBKAIJ-UHFFFAOYSA-N 0.000 description 3
- YNOKAQICKKMEPH-UHFFFAOYSA-N 2-methoxyquinolin-5-amine Chemical compound NC1=CC=CC2=NC(OC)=CC=C21 YNOKAQICKKMEPH-UHFFFAOYSA-N 0.000 description 3
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- 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
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE10215316A DE10215316C1 (de) | 2002-04-02 | 2002-04-02 | Chinolin- und Isochinolin-Derivate, ein pharmazeutisches Mittel und ihre Verwendung als Entzündungshemmer |
PCT/EP2003/003298 WO2003082827A1 (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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UA78304C2 true UA78304C2 (en) | 2007-03-15 |
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UA20041108938A UA78304C2 (en) | 2002-04-02 | 2003-03-29 | Quinoline and isoquinoline derivatives, use thereof as anti-inflammatory agents and pharmaceutical preparation based thereon |
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CN (1) | CN1659144B (sr) |
AR (1) | AR039222A1 (sr) |
AT (1) | ATE355277T1 (sr) |
AU (1) | AU2003215678B2 (sr) |
BR (1) | BR0308967A (sr) |
CA (1) | CA2481012C (sr) |
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DE (2) | DE10215316C1 (sr) |
DK (1) | DK1492771T3 (sr) |
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EC (1) | ECSP045399A (sr) |
ES (1) | ES2282649T3 (sr) |
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HR (1) | HRP20041005B1 (sr) |
IL (1) | IL164292A (sr) |
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MX (1) | MXPA04009684A (sr) |
NO (1) | NO329668B1 (sr) |
NZ (1) | NZ535872A (sr) |
PE (1) | PE20040081A1 (sr) |
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PT (1) | PT1492771E (sr) |
RS (1) | RS50931B (sr) |
SI (1) | SI1492771T1 (sr) |
TW (1) | TWI272267B (sr) |
UA (1) | UA78304C2 (sr) |
UY (1) | UY27748A1 (sr) |
WO (1) | WO2003082827A1 (sr) |
ZA (1) | ZA200408827B (sr) |
Families Citing this family (90)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10346940B3 (de) * | 2003-10-06 | 2005-06-16 | Schering Ag | Substituierte Pentanole, ihre Verwendung zur Herstellung von Arzneimitteln speziell Entzündungshemmer sowie diese enthaltende pharmazeutische Präparate |
US7238707B2 (en) | 2000-07-28 | 2007-07-03 | Schering Ag | Substituted pentanols, a process for their production and their use as anti-inflammatory agents |
CN1633296A (zh) | 2002-03-26 | 2005-06-29 | 贝林格尔·英格海姆药物公司 | 糖皮质素模拟物、其制备方法、药物组合物及其用途 |
TWI328009B (en) | 2003-05-21 | 2010-08-01 | Glaxo Group Ltd | Quinoline derivatives as phosphodiesterase inhibitors |
CA2531060A1 (en) * | 2003-07-01 | 2005-01-13 | Schering Aktiengesellschaft | Heterocyclically-substitued pentanol derivatives, process for their production and their use as anti-inflammatory agents |
GB0316290D0 (en) | 2003-07-11 | 2003-08-13 | Glaxo Group Ltd | Novel compounds |
UY28526A1 (es) | 2003-09-24 | 2005-04-29 | Boehringer Ingelheim Pharma | Miméticos de glucocorticoides, métodos de preparación composiciones farmacéuticas y usos de los mismos |
US7662821B2 (en) | 2003-10-08 | 2010-02-16 | Bayer Schering Pharma Ag | Tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents |
US7638515B2 (en) | 2003-10-08 | 2009-12-29 | Bayer Schering Pharma Aktiengesellschaft | Tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents |
NZ546473A (en) | 2003-10-08 | 2009-09-25 | Bayer Schering Pharma Ag | 1-amino-2-oxy-substituted tetrahydronaphthalene derivatives, methods for the production thereof, and their use as antiphlogistics |
ATE366726T1 (de) * | 2003-10-16 | 2007-08-15 | Boehringer Ingelheim Pharma | Stereoselektive synthese bestimmter trifluormethylsubstituierter alkohole |
US7795272B2 (en) | 2004-03-13 | 2010-09-14 | Boehringer Ingelheim Pharmaceutical, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions and uses thereof |
US20080153859A1 (en) | 2004-04-05 | 2008-06-26 | Hartmut Rehwinkel | Multiply-substituted tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents |
PE20060272A1 (es) | 2004-05-24 | 2006-05-22 | Glaxo Group Ltd | (2r,3r,4s,5r,2'r,3'r,4's,5's)-2,2'-{trans-1,4-ciclohexanodiilbis-[imino(2-{[2-(1-metil-1h-imidazol-4-il)etil]amino}-9h-purin-6,9-diil)]}bis[5-(2-etil-2h-tetrazol-5-il)tetrahidro-3,4-furanodiol] como agonista a2a |
TWI307630B (en) | 2004-07-01 | 2009-03-21 | Glaxo Group Ltd | Immunoglobulins |
GB0418045D0 (en) | 2004-08-12 | 2004-09-15 | Glaxo Group Ltd | Compounds |
DE102004044680B3 (de) * | 2004-09-09 | 2006-06-08 | Schering Ag | Alkyliden-Tetrahydronaphthalinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer sowie diese enthaltende pharmazeutische Präparate |
DE102005020331A1 (de) * | 2005-04-26 | 2006-11-02 | Schering Ag | 5-substituierte Chinolin- und Isochinolin-Derivate, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
US7417056B2 (en) | 2004-11-12 | 2008-08-26 | Schering Ag | 5-substituted quinoline and isoquinoline derivatives, a process for their production and their use as anti-inflammatory agents |
DE102004055633A1 (de) * | 2004-11-12 | 2006-05-18 | Schering Ag | 5-substituierte Chinolin- und Isochinolin-Derivate, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
DE102004063227A1 (de) * | 2004-12-22 | 2006-07-06 | Schering Ag | Tricylische Aminoalkohole, Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
ATE433958T1 (de) | 2004-12-27 | 2009-07-15 | Boehringer Ingelheim Pharma | Glucocorticoid-mimetika, verfahren zu deren herstellung, pharmazeutische zusammensetzungen und deren verwendung |
US7579335B2 (en) | 2005-01-10 | 2009-08-25 | Glaxo Group Limited | Androstane 17α-carbonate derivatives for use in the treatment of allergic and inflammatory conditions |
US7297700B2 (en) | 2005-03-24 | 2007-11-20 | Renovis, Inc. | Bicycloheteroaryl compounds as P2X7 modulators and uses thereof |
AR053346A1 (es) | 2005-03-25 | 2007-05-02 | Glaxo Group Ltd | Compuesto derivado de 8h -pirido (2,3-d) pirimidin -7 ona 2,4,8- trisustituida composicion farmaceutica y uso para preparar una composicion para tratamiento y profilxis de una enfermedad mediada por la quinasa csbp/ rk/p38 |
PE20061193A1 (es) | 2005-03-25 | 2006-12-02 | Glaxo Group Ltd | DERIVADOS DE 3,4-DIHIDROPIRIMIDO[4,5-d]PIRIMIDIN-2-[1H]-0NA COMO INHIBIDORES DE QUINASA p38 |
DE102005018026B4 (de) * | 2005-04-14 | 2006-12-21 | Schering Ag | Substituierte Styrole, Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
DE102005018025A1 (de) * | 2005-04-14 | 2006-11-02 | Schering Ag | Mehrfach substituierte bizyklische Systeme, Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
DE102005017301A1 (de) * | 2005-04-14 | 2006-10-19 | Schering Ag | Substituierte Chromanderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
GB0514809D0 (en) | 2005-07-19 | 2005-08-24 | Glaxo Group Ltd | Compounds |
TW200730498A (en) | 2005-12-20 | 2007-08-16 | Glaxo Group Ltd | Compounds |
EP1834948A1 (de) | 2006-03-15 | 2007-09-19 | Bayer Schering Pharma Aktiengesellschaft | Tetrahydronaphthalinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
TWI464148B (zh) | 2006-03-16 | 2014-12-11 | Evotec Us Inc | 作為p2x7調節劑之雙環雜芳基化合物與其用途 |
MX2008013411A (es) | 2006-04-20 | 2008-11-04 | Glaxo Group Ltd | Nuevos compuestos. |
GB0611587D0 (en) | 2006-06-12 | 2006-07-19 | Glaxo Group Ltd | Novel compounds |
AU2007319590A1 (en) * | 2006-11-09 | 2008-05-22 | Bausch & Lomb Incorporated | Synthesis of selected stereoisomers of certain substituted alcohols |
AU2007329548A1 (en) | 2006-12-06 | 2008-06-12 | Boehringer Ingelheim International Gmbh | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
US20080171873A1 (en) * | 2007-01-12 | 2008-07-17 | Harms Arthur E | Synthesis of selected stereoisomers of certain substituted alcohols |
CN101686680B (zh) | 2007-03-09 | 2015-12-09 | 伊沃泰克美国股份有限公司 | 作为p2x7调节剂的双环杂芳基化合物及其用途 |
PE20081889A1 (es) | 2007-03-23 | 2009-03-05 | Smithkline Beecham Corp | Indol carboxamidas como inhibidores de ikk2 |
EP2016935A1 (en) * | 2007-07-09 | 2009-01-21 | Intendis GmbH | Pharmaceutical composition for topical application of poorly soluble compounds |
AU2009325091A1 (en) | 2008-05-23 | 2010-06-17 | Panmira Pharmaceuticals, Llc | 5-lipoxygenase-activating protein inhibitor |
WO2009147190A1 (en) | 2008-06-05 | 2009-12-10 | Glaxo Group Limited | Novel compounds |
EP2280946B1 (en) | 2008-06-05 | 2016-02-10 | Glaxo Group Limited | 4-carboxamide indazole derivatives useful as inhibitors of p13-kinases |
PT2300472E (pt) | 2008-06-06 | 2012-02-20 | Boehringer Ingelheim Int | Miméticos de glucocorticóides, métodos de os preparar, composições farmacêuticas e suas utilizações |
WO2010094643A1 (en) | 2009-02-17 | 2010-08-26 | Glaxo Group Limited | Quinoline derivatives and their uses for rhinitis and urticaria |
US8524751B2 (en) | 2009-03-09 | 2013-09-03 | GlaxoSmithKline Intellecutual Property Development | 4-oxadiazol-2-YL-indazoles as inhibitors of P13 kinases |
US8354539B2 (en) | 2009-03-10 | 2013-01-15 | Glaxo Group Limited | Indole derivatives as IKK2 inhibitors |
JP2012520845A (ja) | 2009-03-17 | 2012-09-10 | グラクソ グループ リミテッド | Itk阻害剤として使用されるピリミジン誘導体 |
WO2010107957A2 (en) | 2009-03-19 | 2010-09-23 | Merck Sharp & Dohme Corp. | RNA INTERFERENCE MEDIATED INHIBITION OF GATA BINDING PROTEIN 3 (GATA3) GENE EXPRESSION USING SHORT INTERFERING NUCLEIC ACID (siNA) |
WO2010107952A2 (en) | 2009-03-19 | 2010-09-23 | Merck Sharp & Dohme Corp. | RNA INTERFERENCE MEDIATED INHIBITION OF CONNECTIVE TISSUE GROWTH FACTOR (CTGF) GENE EXPRESSION USING SHORT INTERFERING NUCLEIC ACID (siNA) |
EP2408458A1 (en) | 2009-03-19 | 2012-01-25 | Merck Sharp&Dohme Corp. | RNA INTERFERENCE MEDIATED INHIBITION OF SIGNAL TRANSDUCER AND ACTIVATOR OF TRANSCRIPTION 6 (STAT6) GENE EXPRESSION USING SHORT INTERFERING NUCLEIC ACID (siNA) |
CN102439151A (zh) | 2009-03-19 | 2012-05-02 | 默沙东公司 | 使用短干扰核酸(siNA)的RNA干扰介导的BTB和CNC同系物1,碱性亮氨酸拉链转录因子1(Bach1)基因表达的抑制 |
JP2012521760A (ja) | 2009-03-27 | 2012-09-20 | メルク・シャープ・エンド・ドーム・コーポレイション | 低分子干渉核酸(siNA)を用いたアポトーシスシグナル調節キナーゼ1(ASK1)遺伝子発現のRNA干渉媒介性阻害 |
US20120004281A1 (en) | 2009-03-27 | 2012-01-05 | Merck Sharp & Dohme Corp | RNA Interference Mediated Inhibition of the Nerve Growth Factor Beta Chain (NGFB) Gene Expression Using Short Interfering Nucleic Acid (siNA) |
JP2012521764A (ja) | 2009-03-27 | 2012-09-20 | メルク・シャープ・エンド・ドーム・コーポレイション | 低分子干渉核酸(siNA)を用いた胸腺間質性リンパ球新生因子(TSLP)遺伝子発現のRNA干渉媒介性阻害 |
US20120022142A1 (en) | 2009-03-27 | 2012-01-26 | Merck Sharp & Dohme Corp. | RNA Interference Mediated Inhibition of Signal Transducer and Activator of Transcription 1 (STAT1) Gene Expression Using Short Interfering Nucleic Acid (siNA) |
JP2012521765A (ja) | 2009-03-27 | 2012-09-20 | メルク・シャープ・エンド・ドーム・コーポレイション | 低分子干渉核酸(siNA)を用いた細胞内接着分子1(ICAM−1)遺伝子発現のRNA干渉媒介性阻害 |
WO2010122088A1 (en) | 2009-04-24 | 2010-10-28 | Glaxo Group Limited | Pyrazole and triazole carboxamides as crac channel inhibitors |
WO2010122089A1 (en) | 2009-04-24 | 2010-10-28 | Glaxo Group Limited | N-pyrazolyl carboxamides as crac channel inhibitors |
ES2644724T3 (es) | 2009-04-30 | 2017-11-30 | Glaxo Group Limited | Indazoles sustituidos con oxazol como inhibidores de PI3-cinasas |
WO2011016050A2 (en) | 2009-07-31 | 2011-02-10 | Cadila Healthcare Limited | Novel compounds as modulators of glucocorticoid receptors |
JP2013512880A (ja) | 2009-12-03 | 2013-04-18 | グラクソ グループ リミテッド | Pi3−キナーゼ阻害剤としてのインダゾール誘導体 |
EP2507226A1 (en) | 2009-12-03 | 2012-10-10 | Glaxo Group Limited | Novel compounds |
US20120245171A1 (en) | 2009-12-03 | 2012-09-27 | Glaxo Group Limited | Benzpyrazole derivatives as inhibitors of pi3 kinases |
EP3020393B1 (en) | 2009-12-16 | 2020-10-07 | 3M Innovative Properties Company | Formulations and methods for controlling mdi particle size delivery |
WO2011110575A1 (en) | 2010-03-11 | 2011-09-15 | Glaxo Group Limited | Derivatives of 2-[2-(benzo- or pyrido-) thiazolylamino]-6-aminopyridine, useful in the treatment of respiratoric, allergic or inflammatory diseases |
GB201007203D0 (en) | 2010-04-29 | 2010-06-16 | Glaxo Group Ltd | Novel compounds |
EP2614058B1 (en) | 2010-09-08 | 2015-07-08 | GlaxoSmithKline Intellectual Property Development Limited | POLYMORPHS AND SALTS OF N-[5-[4-(5-{[(2R,6S)-2,6-DIMETHYL-4-MORPHOLINYL]METHYL}-& xA;1,3-OXAZOL-2-YL)-1H-INDAZOL-6-YL]-2-(METHYLOXY)-3-PYRIDINYL]METHANESULFONAMIDE |
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AU2014321420B2 (en) | 2013-09-22 | 2017-06-15 | Sunshine Lake Pharma Co., Ltd. | Substituted aminopyrimidine compounds and methods of use |
US20160256466A1 (en) | 2013-10-17 | 2016-09-08 | Glaxosmithkline Intellectual Property Development Limited | Pi3k inhibitor for treatment of respiratory disease |
EP3057588A1 (en) | 2013-10-17 | 2016-08-24 | GlaxoSmithKline Intellectual Property Development Limited | Pi3k inhibitor for treatment of respiratory disease |
WO2015148867A1 (en) | 2014-03-28 | 2015-10-01 | Calitor Sciences, Llc | Substituted heteroaryl compounds and methods of use |
US20170100385A1 (en) | 2014-05-12 | 2017-04-13 | Glaxosmithkline Intellectual Property (No. 2) Limited | Pharmaceutical compositions comprising danirixin for treating infectious diseases |
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GB201602527D0 (en) | 2016-02-12 | 2016-03-30 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
JP2019524792A (ja) | 2016-08-08 | 2019-09-05 | 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Glaxosmithkline Intellectual Property Development Limited | 化合物 |
GB201706102D0 (en) | 2017-04-18 | 2017-05-31 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
GB201712081D0 (en) | 2017-07-27 | 2017-09-13 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
US10683297B2 (en) | 2017-11-19 | 2020-06-16 | Calitor Sciences, Llc | Substituted heteroaryl compounds and methods of use |
US10751339B2 (en) | 2018-01-20 | 2020-08-25 | Sunshine Lake Pharma Co., Ltd. | Substituted aminopyrimidine compounds and methods of use |
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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 |
Family Cites Families (5)
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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 |
DE10038639A1 (de) | 2000-07-28 | 2002-02-21 | 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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