DE2854341C2 - - Google Patents
Info
- Publication number
- DE2854341C2 DE2854341C2 DE2854341A DE2854341A DE2854341C2 DE 2854341 C2 DE2854341 C2 DE 2854341C2 DE 2854341 A DE2854341 A DE 2854341A DE 2854341 A DE2854341 A DE 2854341A DE 2854341 C2 DE2854341 C2 DE 2854341C2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- trifluoromethyl
- quinolinylamino
- fluorobenzoic acid
- product
- 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 - Fee Related
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 50
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 14
- 150000007513 acids Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- NBHKDVFSWLHYJR-UHFFFAOYSA-N 5-fluoro-2-(quinolin-4-ylamino)benzoic acid Chemical class OC(=O)C1=CC(F)=CC=C1NC1=CC=NC2=CC=CC=C12 NBHKDVFSWLHYJR-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 150000003254 radicals Chemical group 0.000 claims description 2
- XLEJHSGYBLEMCI-UHFFFAOYSA-N 2,3-dihydroxypropyl 5-fluoro-2-[[8-(trifluoromethyl)quinolin-4-yl]amino]benzoate Chemical compound OCC(O)COC(=O)C1=CC(F)=CC=C1NC1=CC=NC2=C(C(F)(F)F)C=CC=C12 XLEJHSGYBLEMCI-UHFFFAOYSA-N 0.000 claims 1
- XAABQOXNZOODQY-UHFFFAOYSA-N 2-(dimethylamino)ethyl 5-fluoro-2-[[8-(trifluoromethyl)quinolin-4-yl]amino]benzoate Chemical compound CN(C)CCOC(=O)C1=CC(F)=CC=C1NC1=CC=NC2=C(C(F)(F)F)C=CC=C12 XAABQOXNZOODQY-UHFFFAOYSA-N 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- DCBSHORRWZKAKO-UHFFFAOYSA-N rac-1-monomyristoylglycerol Chemical compound CCCCCCCCCCCCCC(=O)OCC(O)CO DCBSHORRWZKAKO-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- -1 formic acid Chemical class 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 238000010992 reflux Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000002585 base Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 230000000202 analgesic effect Effects 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- FTMNSXDJPJHNSF-UHFFFAOYSA-N 2-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1C1=CC=CC(C(F)(F)F)=C1 FTMNSXDJPJHNSF-UHFFFAOYSA-N 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- LYEAUCRITXBJTG-UHFFFAOYSA-N methyl 2-[(7-chloroquinolin-4-yl)amino]-5-fluorobenzoate Chemical compound COC(=O)C1=CC(F)=CC=C1NC1=CC=NC2=CC(Cl)=CC=C12 LYEAUCRITXBJTG-UHFFFAOYSA-N 0.000 description 4
- UAJCXPLDRIQWRP-UHFFFAOYSA-N 2-[(7-chloroquinolin-4-yl)amino]-5-fluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=CC=C1NC1=CC=NC2=CC(Cl)=CC=C12 UAJCXPLDRIQWRP-UHFFFAOYSA-N 0.000 description 3
- HQYCQIWWCBOKKI-UHFFFAOYSA-N 5-fluoro-2-[[7-(trifluoromethyl)quinolin-4-yl]amino]benzoic acid Chemical compound FC(C1=CC=C2C(=CC=NC2=C1)NC1=C(C(=O)O)C=C(C=C1)F)(F)F HQYCQIWWCBOKKI-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229960002887 deanol Drugs 0.000 description 3
- PUDDYSBKCDKATP-UHFFFAOYSA-N methyl 2-amino-5-fluorobenzoate Chemical compound COC(=O)C1=CC(F)=CC=C1N PUDDYSBKCDKATP-UHFFFAOYSA-N 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- HXEWMTXDBOQQKO-UHFFFAOYSA-N 4,7-dichloroquinoline Chemical compound ClC1=CC=NC2=CC(Cl)=CC=C21 HXEWMTXDBOQQKO-UHFFFAOYSA-N 0.000 description 2
- JBAFPLJQMLMGAH-UHFFFAOYSA-N 5-fluoro-2-[[8-(trifluoromethyl)quinolin-4-yl]amino]benzoic acid Chemical compound OC(=O)C1=CC(F)=CC=C1NC1=CC=NC2=C(C(F)(F)F)C=CC=C12 JBAFPLJQMLMGAH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000010425 asbestos Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- FRLHRTUBWUUAFG-UHFFFAOYSA-N methyl 5-fluoro-2-[[8-(trifluoromethyl)quinolin-4-yl]amino]benzoate Chemical compound COC(=O)C1=CC(F)=CC=C1NC1=CC=NC2=C(C(F)(F)F)C=CC=C12 FRLHRTUBWUUAFG-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052895 riebeckite Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- BLSPUXXZJIRRRV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-[(7-chloroquinolin-4-yl)amino]-5-fluorobenzoate Chemical compound CN(C)CCOC(=O)C1=CC(F)=CC=C1NC1=CC=NC2=CC(Cl)=CC=C12 BLSPUXXZJIRRRV-UHFFFAOYSA-N 0.000 description 1
- VKJPDYALTJZMKG-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-[(8-chloroquinolin-4-yl)amino]-5-fluorobenzoate Chemical compound CN(C)CCOC(=O)C1=CC(F)=CC=C1NC1=CC=NC2=C(Cl)C=CC=C12 VKJPDYALTJZMKG-UHFFFAOYSA-N 0.000 description 1
- KKINZXMSPZQQQR-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-[(8-chloroquinolin-4-yl)amino]-5-fluorobenzoate;hydrochloride Chemical compound Cl.CN(C)CCOC(=O)C1=CC(F)=CC=C1NC1=CC=NC2=C(Cl)C=CC=C12 KKINZXMSPZQQQR-UHFFFAOYSA-N 0.000 description 1
- NPHULPIAPWNOOH-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(2,3-dihydroindol-1-ylmethyl)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CN1CCC2=CC=CC=C12 NPHULPIAPWNOOH-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- SDPCOMBBZFETLG-UHFFFAOYSA-N 4,8-dichloroquinoline Chemical compound C1=CC=C2C(Cl)=CC=NC2=C1Cl SDPCOMBBZFETLG-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- LLRQVSZVVAKRJA-UHFFFAOYSA-N 4-chloro-7-(trifluoromethyl)quinoline Chemical compound ClC1=CC=NC2=CC(C(F)(F)F)=CC=C21 LLRQVSZVVAKRJA-UHFFFAOYSA-N 0.000 description 1
- LINGICLAECZKAW-UHFFFAOYSA-N 4-chloro-8-(trifluoromethyl)quinoline Chemical compound C1=CN=C2C(C(F)(F)F)=CC=CC2=C1Cl LINGICLAECZKAW-UHFFFAOYSA-N 0.000 description 1
- FPQMGQZTBWIHDN-UHFFFAOYSA-N 5-fluoroanthranilic acid Chemical compound NC1=CC=C(F)C=C1C(O)=O FPQMGQZTBWIHDN-UHFFFAOYSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 239000004475 Arginine Chemical class 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical class NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Chemical class OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical class C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229950003188 isovaleryl diethylamide Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- QVDHDLGBWADBND-UHFFFAOYSA-N methyl 2-[(8-chloroquinolin-4-yl)amino]-5-fluorobenzoate Chemical compound COC(=O)C1=CC(F)=CC=C1NC1=CC=NC2=C(Cl)C=CC=C12 QVDHDLGBWADBND-UHFFFAOYSA-N 0.000 description 1
- WGRQWIFSBUXXBX-UHFFFAOYSA-N methyl 5-fluoro-2-[[7-(trifluoromethyl)quinolin-4-yl]amino]benzoate Chemical compound COC(=O)C1=CC(F)=CC=C1NC1=CC=NC2=CC(C(F)(F)F)=CC=C12 WGRQWIFSBUXXBX-UHFFFAOYSA-N 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 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
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/44—Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7737836A FR2411833A1 (fr) | 1977-12-15 | 1977-12-15 | Nouveaux derives de l'acide 2(/4-quinoleinyl/amino) 5-fluoro benzoique, leur procede de preparation et leur application comme medicament |
| FR7737835A FR2411832A1 (fr) | 1977-12-15 | 1977-12-15 | Nouveaux derives de l'acide 2/(4-quinoleinyl) amino/5-fluorobenzoique, leur procede de preparation et leur application comme medicament. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2854341A1 DE2854341A1 (de) | 1979-06-28 |
| DE2854341C2 true DE2854341C2 (en, 2012) | 1990-05-23 |
Family
ID=26220343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782854341 Granted DE2854341A1 (de) | 1977-12-15 | 1978-12-15 | Neue derivate der 2- eckige klammer auf (4-chinolinyl)-amino eckige klammer zu -5-fluorbenzoesaeure, verfahren zu deren herstellung, deren verwendung als arzneimittel und die sie enthaltenden pharmazeutischen zusammensetzungen |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4233305A (en, 2012) |
| JP (1) | JPS5488277A (en, 2012) |
| AR (1) | AR224116A1 (en, 2012) |
| AT (1) | AT365578B (en, 2012) |
| AU (1) | AU520983B2 (en, 2012) |
| CA (1) | CA1115276A (en, 2012) |
| CH (1) | CH636350A5 (en, 2012) |
| DE (1) | DE2854341A1 (en, 2012) |
| DK (1) | DK149845C (en, 2012) |
| ES (1) | ES475686A1 (en, 2012) |
| FI (1) | FI70574C (en, 2012) |
| GB (1) | GB2010243B (en, 2012) |
| HU (1) | HU177031B (en, 2012) |
| IE (1) | IE47618B1 (en, 2012) |
| IL (1) | IL56156A (en, 2012) |
| IT (1) | IT1107671B (en, 2012) |
| LU (1) | LU80660A1 (en, 2012) |
| NL (1) | NL7812206A (en, 2012) |
| PT (1) | PT68916A (en, 2012) |
| SE (1) | SE448091B (en, 2012) |
| SU (1) | SU837322A3 (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6322584A (ja) * | 1986-07-15 | 1988-01-30 | Senjiyu Seiyaku Kk | １−ハイドロキシ−５−オキソ−５Ｈ−ピリド〔３，２−ａ〕フエノキサジン−３−カルボン酸エステル類 |
| IL89029A (en) * | 1988-01-29 | 1993-01-31 | Lilly Co Eli | Fungicidal quinoline and cinnoline derivatives, compositions containing them, and fungicidal methods of using them |
| IS4164A (is) * | 1993-06-11 | 1994-12-12 | Ab Astra | Efnasambönd sem hindra flæði magasýru |
| US5578607A (en) * | 1993-12-17 | 1996-11-26 | The Procter & Gamble Company | 6-(2-imidazolinylamino)quinoline compounds useful as alpha-2 adrenoceptor agonists |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3232944A (en) * | 1966-02-01 | Monoglycerides 0f (carbgxy pl-ienyl amtno) chlgroqukngltnes | ||
| CH408915A (fr) * | 1962-02-16 | 1966-03-15 | Roussel Uclaf | Procédé de préparation d'un nouveau composé utilisable, notamment, pour le traitement des manifestations inflammatoires et/ou douloureuses |
| CA731646A (en) * | 1962-05-08 | 1966-04-05 | Roussel-Uclaf | 4-(2'(.beta.-MORPHOLYLETHOXYCARBONYL) PHENYLAMINE) 7-CHLORO QUINOLEINE ET SES SELS, AINSI QUE LEUR PROCEDE DE PREPARATION |
| FR6935M (en, 2012) * | 1967-12-29 | 1969-05-05 | ||
| FR7870M (en, 2012) * | 1968-11-08 | 1970-04-27 | ||
| ZA726593B (en) * | 1971-10-19 | 1973-06-27 | Abbott Lab | Novel derivatives of 2,3-dihydroxypropyl-n-(7 or 8-chloro-4-quinolinyl)anthranilate |
| CH585221A5 (en, 2012) * | 1972-07-28 | 1977-02-28 | Synthelabo | |
| US3971789A (en) * | 1972-10-21 | 1976-07-27 | John Wyeth & Brother Limited | O-(4-Quinolylamino)benzamides |
| FR2233059B1 (en, 2012) * | 1973-06-13 | 1976-09-03 | Roussel Uclaf | |
| GB1474296A (en) * | 1975-01-23 | 1977-05-18 | Wyeth John & Brother Ltd | 4-aminoquinoline derivatives |
-
1978
- 1978-11-16 SE SE7811839A patent/SE448091B/sv not_active IP Right Cessation
- 1978-12-04 ES ES475686A patent/ES475686A1/es not_active Expired
- 1978-12-06 US US05/966,964 patent/US4233305A/en not_active Expired - Lifetime
- 1978-12-07 SU SU782696357A patent/SU837322A3/ru active
- 1978-12-08 IL IL56156A patent/IL56156A/xx unknown
- 1978-12-13 FI FI783833A patent/FI70574C/fi not_active IP Right Cessation
- 1978-12-14 HU HU78RO1003A patent/HU177031B/hu not_active IP Right Cessation
- 1978-12-14 CA CA317,952A patent/CA1115276A/fr not_active Expired
- 1978-12-14 IE IE2476/78A patent/IE47618B1/en unknown
- 1978-12-14 IT IT52296/78A patent/IT1107671B/it active
- 1978-12-14 PT PT68916A patent/PT68916A/pt unknown
- 1978-12-14 AR AR274807A patent/AR224116A1/es active
- 1978-12-14 LU LU80660A patent/LU80660A1/xx unknown
- 1978-12-14 AU AU42528/78A patent/AU520983B2/en not_active Expired
- 1978-12-14 GB GB7848546A patent/GB2010243B/en not_active Expired
- 1978-12-14 JP JP15380478A patent/JPS5488277A/ja active Granted
- 1978-12-14 DK DK561278A patent/DK149845C/da not_active IP Right Cessation
- 1978-12-15 DE DE19782854341 patent/DE2854341A1/de active Granted
- 1978-12-15 AT AT0897378A patent/AT365578B/de not_active IP Right Cessation
- 1978-12-15 CH CH1279478A patent/CH636350A5/fr not_active IP Right Cessation
- 1978-12-15 NL NL7812206A patent/NL7812206A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FI70574C (fi) | 1986-09-24 |
| JPS631305B2 (en, 2012) | 1988-01-12 |
| SU837322A3 (ru) | 1981-06-07 |
| IT1107671B (it) | 1985-11-25 |
| PT68916A (fr) | 1979-01-01 |
| SE7811839L (sv) | 1979-06-16 |
| IE782476L (en) | 1979-06-15 |
| NL7812206A (nl) | 1979-06-19 |
| CH636350A5 (fr) | 1983-05-31 |
| IL56156A (en) | 1984-11-30 |
| US4233305A (en) | 1980-11-11 |
| IT7852296A0 (it) | 1978-12-14 |
| DK149845C (da) | 1987-03-02 |
| ES475686A1 (es) | 1979-04-16 |
| DK561278A (da) | 1979-06-16 |
| IL56156A0 (en) | 1979-03-12 |
| AR224116A1 (es) | 1981-10-30 |
| DE2854341A1 (de) | 1979-06-28 |
| IE47618B1 (en) | 1984-05-02 |
| AT365578B (de) | 1982-01-25 |
| AU520983B2 (en) | 1982-03-11 |
| GB2010243B (en) | 1982-05-19 |
| LU80660A1 (fr) | 1979-07-20 |
| SE448091B (sv) | 1987-01-19 |
| HU177031B (hu) | 1981-06-28 |
| DK149845B (da) | 1986-10-13 |
| FI783833A7 (fi) | 1979-06-16 |
| AU4252878A (en) | 1979-06-21 |
| FI70574B (fi) | 1986-06-06 |
| JPS5488277A (en) | 1979-07-13 |
| CA1115276A (fr) | 1981-12-29 |
| ATA897378A (de) | 1981-06-15 |
| GB2010243A (en) | 1979-06-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: ZUMSTEIN SEN., F., DR. ASSMANN, E., DIPL.-CHEM. DR |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |