DE2928583A1 - Verfahren zur herstellung von carbostyrilderivaten - Google Patents
Verfahren zur herstellung von carbostyrilderivatenInfo
- Publication number
- DE2928583A1 DE2928583A1 DE19792928583 DE2928583A DE2928583A1 DE 2928583 A1 DE2928583 A1 DE 2928583A1 DE 19792928583 DE19792928583 DE 19792928583 DE 2928583 A DE2928583 A DE 2928583A DE 2928583 A1 DE2928583 A1 DE 2928583A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- carbon atoms
- general formula
- nitro
- carried out
- 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.)
- Withdrawn
Links
- 230000002785 anti-thrombosis Effects 0.000 title abstract description 3
- 239000003146 anticoagulant agent Substances 0.000 title abstract 2
- LAOMDZFORKFNPV-UHFFFAOYSA-N 3-(2-aminophenyl)propanoic acid Chemical compound NC1=CC=CC=C1CCC(O)=O LAOMDZFORKFNPV-UHFFFAOYSA-N 0.000 title 1
- 239000004041 inotropic agent Substances 0.000 title 1
- -1 hydroxy, methoxy, amino, acetylamino Chemical group 0.000 claims abstract description 52
- 238000000034 method Methods 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000005843 halogen group Chemical group 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims abstract description 6
- 229910052751 metal Inorganic materials 0.000 claims abstract description 6
- 239000002184 metal Substances 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 230000000269 nucleophilic effect Effects 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 125000006839 xylylene group Chemical group 0.000 claims abstract description 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims abstract description 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000004429 atom Chemical group 0.000 claims abstract description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000004475 heteroaralkyl group Chemical group 0.000 claims abstract description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 3
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims abstract 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 16
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- 229960000583 acetic acid Drugs 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000012362 glacial acetic acid Substances 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical group 0.000 claims 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 230000009090 positive inotropic effect Effects 0.000 abstract description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 238000002844 melting Methods 0.000 description 42
- 230000008018 melting Effects 0.000 description 42
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 150000002828 nitro derivatives Chemical class 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- RGHZFRRLCRAWPU-UHFFFAOYSA-N methyl 3-(5-hydroxy-2-nitrophenyl)prop-2-enoate Chemical compound COC(=O)C=CC1=CC(O)=CC=C1[N+]([O-])=O RGHZFRRLCRAWPU-UHFFFAOYSA-N 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- UXBIFQZFTVFCDC-UHFFFAOYSA-N 6-(4-pyridin-2-ylsulfonylbutoxy)-1h-quinolin-2-one Chemical compound C1=CC2=NC(O)=CC=C2C=C1OCCCCS(=O)(=O)C1=CC=CC=N1 UXBIFQZFTVFCDC-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229940046892 lead acetate Drugs 0.000 description 3
- 239000011981 lindlar catalyst Substances 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- BXXWFOGWXLJPPA-UHFFFAOYSA-N 2,3-dibromobutane Chemical compound CC(Br)C(C)Br BXXWFOGWXLJPPA-UHFFFAOYSA-N 0.000 description 2
- SPWWWLCTUNXBRR-UHFFFAOYSA-N 3-(5-hydroxy-2-nitrophenyl)prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC(O)=CC=C1[N+]([O-])=O SPWWWLCTUNXBRR-UHFFFAOYSA-N 0.000 description 2
- AJRIOFDACOMVOP-UHFFFAOYSA-N 5-(4-bromobutoxy)-2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(OCCCCBr)C=C1C=O AJRIOFDACOMVOP-UHFFFAOYSA-N 0.000 description 2
- UURXBTHJZQYWEK-UHFFFAOYSA-N 6-[4-(3,4-dichlorophenyl)sulfanylbutoxy]-1h-quinolin-2-one Chemical compound C1=C(Cl)C(Cl)=CC=C1SCCCCOC1=CC=C(NC(=O)C=C2)C2=C1 UURXBTHJZQYWEK-UHFFFAOYSA-N 0.000 description 2
- MKDYXDJTTWXMAH-UHFFFAOYSA-N 6-[4-(3,4-dichlorophenyl)sulfonylbutoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)CCCCOC1=CC=C(NC(=O)CC2)C2=C1 MKDYXDJTTWXMAH-UHFFFAOYSA-N 0.000 description 2
- 229910021554 Chromium(II) chloride Inorganic materials 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- XBWRJSSJWDOUSJ-UHFFFAOYSA-L chromium(ii) chloride Chemical compound Cl[Cr]Cl XBWRJSSJWDOUSJ-UHFFFAOYSA-L 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 2
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 description 1
- ADSNHKTXYJZXDF-UHFFFAOYSA-N 3-hydroxy-2-nitrobenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1[N+]([O-])=O ADSNHKTXYJZXDF-UHFFFAOYSA-N 0.000 description 1
- ICFZWESBQTTYOC-UHFFFAOYSA-N 4-(4-bromobutylsulfinyl)-1,2-dichlorobenzene Chemical compound ClC1=CC=C(S(=O)CCCCBr)C=C1Cl ICFZWESBQTTYOC-UHFFFAOYSA-N 0.000 description 1
- UTTJAIFHRUAFED-UHFFFAOYSA-N 5-hydroxy-3,4-dihydro-2(1h)-quinolinone Chemical compound N1C(=O)CCC2=C1C=CC=C2O UTTJAIFHRUAFED-UHFFFAOYSA-N 0.000 description 1
- UWTKTVZMVAFAGZ-UHFFFAOYSA-N 6-(4-cyclohexylsulfinylbutoxy)-3,4-dihydro-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCS(=O)C1CCCCC1 UWTKTVZMVAFAGZ-UHFFFAOYSA-N 0.000 description 1
- KBVIQLRCIJFIMF-UHFFFAOYSA-N 6-(4-pyridin-2-ylsulfonylbutoxy)-3,4-dihydro-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCS(=O)(=O)C1=CC=CC=N1 KBVIQLRCIJFIMF-UHFFFAOYSA-N 0.000 description 1
- FFOAMIRPYWTXQX-UHFFFAOYSA-N 6-(4-quinolin-2-ylsulfinylbutoxy)-1h-quinolin-2-one Chemical compound C1=CC=CC2=NC(S(CCCCOC=3C=C4C=CC(=O)NC4=CC=3)=O)=CC=C21 FFOAMIRPYWTXQX-UHFFFAOYSA-N 0.000 description 1
- DUDLVNRPJPQAPX-UHFFFAOYSA-N 6-[2-(benzenesulfinyl)ethoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCS(=O)C1=CC=CC=C1 DUDLVNRPJPQAPX-UHFFFAOYSA-N 0.000 description 1
- SXSYHNCKTQPJPL-UHFFFAOYSA-N 6-[4-(2-methoxyphenyl)sulfinylbutoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound COC1=CC=CC=C1S(=O)CCCCOC1=CC=C(NC(=O)CC2)C2=C1 SXSYHNCKTQPJPL-UHFFFAOYSA-N 0.000 description 1
- OLKNUHLCNLDYJN-UHFFFAOYSA-N 6-[4-(3,4-dichlorophenyl)sulfanylbutoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=C(Cl)C(Cl)=CC=C1SCCCCOC1=CC=C(NC(=O)CC2)C2=C1 OLKNUHLCNLDYJN-UHFFFAOYSA-N 0.000 description 1
- PPABMMXAJNWWHO-UHFFFAOYSA-N 6-[4-(3,5-ditert-butyl-4-hydroxyphenyl)sulfinylbutoxy]-1h-quinolin-2-one Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(S(=O)CCCCOC=2C=C3C=CC(=O)NC3=CC=2)=C1 PPABMMXAJNWWHO-UHFFFAOYSA-N 0.000 description 1
- OIDGRMDWLNZHHE-UHFFFAOYSA-N 6-[4-(4-amino-3,5-dibromophenyl)sulfinylbutoxy]-1h-quinolin-2-one Chemical compound C1=C(Br)C(N)=C(Br)C=C1S(=O)CCCCOC1=CC=C(NC(=O)C=C2)C2=C1 OIDGRMDWLNZHHE-UHFFFAOYSA-N 0.000 description 1
- GITZAIRZLBVXDF-UHFFFAOYSA-N 6-[4-(4-amino-3,5-dibromophenyl)sulfinylbutoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=C(Br)C(N)=C(Br)C=C1S(=O)CCCCOC1=CC=C(NC(=O)CC2)C2=C1 GITZAIRZLBVXDF-UHFFFAOYSA-N 0.000 description 1
- LOVABRWXJRAPRS-UHFFFAOYSA-N 6-[4-(4-chlorophenyl)sulfinylbutoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC(Cl)=CC=C1S(=O)CCCCOC1=CC=C(NC(=O)CC2)C2=C1 LOVABRWXJRAPRS-UHFFFAOYSA-N 0.000 description 1
- NMUWLPZCRYURDW-UHFFFAOYSA-N 6-[4-(4-cyclohexylphenyl)sulfinylbutoxy]-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)C=CC2=CC=1OCCCCS(=O)C(C=C1)=CC=C1C1CCCCC1 NMUWLPZCRYURDW-UHFFFAOYSA-N 0.000 description 1
- YKKCAQSYVSZODS-UHFFFAOYSA-N 6-[4-(4-phenylphenyl)sulfinylbutoxy]-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)C=CC2=CC=1OCCCCS(=O)C(C=C1)=CC=C1C1=CC=CC=C1 YKKCAQSYVSZODS-UHFFFAOYSA-N 0.000 description 1
- DVHFRAJZCBPZIP-UHFFFAOYSA-N 6-[4-(benzenesulfinyl)butoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCS(=O)C1=CC=CC=C1 DVHFRAJZCBPZIP-UHFFFAOYSA-N 0.000 description 1
- KSUKFRAZFFLINQ-UHFFFAOYSA-N 6-[4-(benzenesulfinyl)butoxy]-4-methyl-1h-quinolin-2-one Chemical compound C1=C2C(C)=CC(=O)NC2=CC=C1OCCCCS(=O)C1=CC=CC=C1 KSUKFRAZFFLINQ-UHFFFAOYSA-N 0.000 description 1
- AARFVSSGWMEZIE-UHFFFAOYSA-N 6-[4-(benzenesulfinyl)butoxy]-5-bromo-1h-quinolin-2-one Chemical compound C1=CC=2NC(=O)C=CC=2C(Br)=C1OCCCCS(=O)C1=CC=CC=C1 AARFVSSGWMEZIE-UHFFFAOYSA-N 0.000 description 1
- IBTKXKPOXYRRTF-UHFFFAOYSA-N 6-[4-(benzenesulfonyl)butoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCS(=O)(=O)C1=CC=CC=C1 IBTKXKPOXYRRTF-UHFFFAOYSA-N 0.000 description 1
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical compound N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
- LKLSFDWYIBUGNT-UHFFFAOYSA-N 7-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical compound C1CC(=O)NC2=CC(O)=CC=C21 LKLSFDWYIBUGNT-UHFFFAOYSA-N 0.000 description 1
- UDKMDIKMJWOSJP-UHFFFAOYSA-N 8-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical compound C1CC(=O)NC2=C1C=CC=C2O UDKMDIKMJWOSJP-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BQFYGQSOQVOJAS-UHFFFAOYSA-N C(O)(O)=O.[N+](=O)([O-])C1=C(C=O)C=C(C=C1)O Chemical compound C(O)(O)=O.[N+](=O)([O-])C1=C(C=O)C=C(C=C1)O BQFYGQSOQVOJAS-UHFFFAOYSA-N 0.000 description 1
- ZWSJTKSIRMBTRY-UHFFFAOYSA-N CCC(COC(=CC1=CC(=CC=C1)S(=O)C2=CC(=C(C=C2)Cl)Cl)C(=O)OC)[N+](=O)[O-] Chemical compound CCC(COC(=CC1=CC(=CC=C1)S(=O)C2=CC(=C(C=C2)Cl)Cl)C(=O)OC)[N+](=O)[O-] ZWSJTKSIRMBTRY-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- 238000010917 Friedel-Crafts cyclization Methods 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 238000005899 aromatization reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000013345 egg yolk Nutrition 0.000 description 1
- 210000002969 egg yolk Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- ILAIRHNIGUVLCZ-UHFFFAOYSA-N methyl 3-[2-nitro-5-(4-pyridin-2-ylsulfanylbutoxy)phenyl]prop-2-enoate Chemical compound COC(C=CC1=C(C=CC(=C1)OCCCCSC1=NC=CC=C1)[N+](=O)[O-])=O ILAIRHNIGUVLCZ-UHFFFAOYSA-N 0.000 description 1
- RIJAFJFYYMYUJM-UHFFFAOYSA-N methyl 3-[5-(4-bromobutoxy)-2-nitrophenyl]prop-2-enoate Chemical compound COC(=O)C=CC1=CC(OCCCCBr)=CC=C1[N+]([O-])=O RIJAFJFYYMYUJM-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 150000003459 sulfonic acid esters Chemical group 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- 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
- C07D215/36—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Cardiology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792928583 DE2928583A1 (de) | 1979-07-14 | 1979-07-14 | Verfahren zur herstellung von carbostyrilderivaten |
| FI792426A FI70408C (fi) | 1979-07-14 | 1979-08-03 | Foerfarande foer framstaellning av terapeutiskt aktiva karbostyrilderivat |
| DK342079A DK150156C (da) | 1979-07-14 | 1979-08-15 | Analogifremgangsmaade til fremstilling af carbostyrilderivater |
| NO792659A NO154131C (no) | 1979-07-14 | 1979-08-15 | Analogifremgangsmaate for fremstilling av terapeutisk aktive karbostyrilderivater. |
| GR61730A GR67622B (cs) | 1979-07-14 | 1980-04-21 | |
| JP6999180A JPS5616470A (en) | 1979-07-14 | 1980-05-26 | Novel manufacture of carbostyril derivative |
| ES491859A ES8200660A1 (es) | 1979-07-14 | 1980-05-27 | Procedimiento mejorado para la preparacion de derivados de carbostirilo |
| AT306480A AT375648B (de) | 1979-07-14 | 1980-06-11 | Verfahren zur herstellung von neuen carbostyrilderivaten |
| PT7153080A PT71530B (de) | 1979-07-14 | 1980-07-10 | Verfahren zur herstellung von carbostyrilderivaten |
| CA000355992A CA1156657A (en) | 1979-07-14 | 1980-07-11 | Process for the preparation of pharmacologically active carbostyril derivatives |
| ES498465A ES498465A0 (es) | 1979-07-14 | 1981-01-13 | Procedimiento mejorado para la preparacion de derivados de carbostirilo |
| ES498466A ES498466A0 (es) | 1979-07-14 | 1981-01-13 | Procedimiento mejorado para la preparacion de derivados de carbostirilo |
| AT246483A AT375925B (de) | 1979-07-14 | 1983-07-05 | Verfahren zur herstellung von neuen carbostyrilderivaten |
| AT246583A AT376209B (de) | 1979-07-14 | 1983-07-05 | Verfahren zur herstellung von neuen carbostyrilderivaten |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792928583 DE2928583A1 (de) | 1979-07-14 | 1979-07-14 | Verfahren zur herstellung von carbostyrilderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2928583A1 true DE2928583A1 (de) | 1981-01-29 |
Family
ID=6075786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792928583 Withdrawn DE2928583A1 (de) | 1979-07-14 | 1979-07-14 | Verfahren zur herstellung von carbostyrilderivaten |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5616470A (cs) |
| DE (1) | DE2928583A1 (cs) |
| DK (1) | DK150156C (cs) |
| FI (1) | FI70408C (cs) |
| NO (1) | NO154131C (cs) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4442111A (en) * | 1981-07-25 | 1984-04-10 | Dr. Karl Thomae Gesellschaft Mit Beschrankter Haftung | Antithrombotic sulfimino and sulfoximino indolinones-2 |
| US4487772A (en) * | 1981-02-17 | 1984-12-11 | Otsuka Pharmaceutical Co. Ltd. | Carbostyril derivatives and their salts |
| US5008274A (en) * | 1986-04-02 | 1991-04-16 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivatives and salts thereof and pharmaceutical composition for inhibiting adhesion of thrombocytes |
| US5434164A (en) * | 1986-04-02 | 1995-07-18 | Otsuka Pharmaceutical Co. Ltd. | Carbostyril derivatives and salts thereof and pharmaceutical compositions for inhibiting adhesion of thrombocytes |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU532361B2 (en) * | 1981-09-01 | 1983-09-29 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5321176A (en) * | 1976-08-09 | 1978-02-27 | Otsuka Pharmaceut Co Ltd | Carbostyryl derivatives |
-
1979
- 1979-07-14 DE DE19792928583 patent/DE2928583A1/de not_active Withdrawn
- 1979-08-03 FI FI792426A patent/FI70408C/fi not_active IP Right Cessation
- 1979-08-15 NO NO792659A patent/NO154131C/no unknown
- 1979-08-15 DK DK342079A patent/DK150156C/da not_active IP Right Cessation
-
1980
- 1980-05-26 JP JP6999180A patent/JPS5616470A/ja active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4487772A (en) * | 1981-02-17 | 1984-12-11 | Otsuka Pharmaceutical Co. Ltd. | Carbostyril derivatives and their salts |
| US4442111A (en) * | 1981-07-25 | 1984-04-10 | Dr. Karl Thomae Gesellschaft Mit Beschrankter Haftung | Antithrombotic sulfimino and sulfoximino indolinones-2 |
| US5008274A (en) * | 1986-04-02 | 1991-04-16 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivatives and salts thereof and pharmaceutical composition for inhibiting adhesion of thrombocytes |
| US5434164A (en) * | 1986-04-02 | 1995-07-18 | Otsuka Pharmaceutical Co. Ltd. | Carbostyril derivatives and salts thereof and pharmaceutical compositions for inhibiting adhesion of thrombocytes |
Also Published As
| Publication number | Publication date |
|---|---|
| DK150156C (da) | 1987-10-12 |
| JPS5616470A (en) | 1981-02-17 |
| FI70408C (fi) | 1986-09-19 |
| DK150156B (da) | 1986-12-22 |
| NO154131B (no) | 1986-04-14 |
| FI792426A7 (fi) | 1981-01-15 |
| NO792659L (no) | 1981-01-15 |
| JPS6326751B2 (cs) | 1988-05-31 |
| DK342079A (da) | 1981-01-15 |
| FI70408B (fi) | 1986-03-27 |
| NO154131C (no) | 1986-07-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2809720C2 (cs) | ||
| EP0045375B1 (de) | Verfahren zur Herstellung von Chinolinen, Naphthyridinen und anderen Stickstoff-bi-heterocyclen | |
| DE1793837C2 (de) | N-(Carbalkoxy-acetyl)-diphenylamine | |
| DE2928583A1 (de) | Verfahren zur herstellung von carbostyrilderivaten | |
| DE2757335C3 (de) | Verfahren zur O-Methylierung von Hydroxyaporphinen | |
| EP0380712B1 (de) | Verfahren zur Herstellung von 2,6-Dichlordiphenylaminessigsäurederivaten | |
| DE69119961T2 (de) | Verfahren zur Reduzierung von Carbonyl enthaltendem Akridin | |
| EP0653423B1 (de) | Verfahren zur Herstellung von substituierten Chinazolin-2,4-dionen | |
| DE2025363A1 (en) | Bactericidal cycloalkanoquinolone derivs from - cycloalkanoquinoline derivs | |
| CH445492A (de) | Verfahren zur Herstellung von in 1-Stellung acylierten a-(3-Indolyl)-niederaliphatischen-säuren | |
| DE69409101T2 (de) | Verfahren zur herstellung von 6-fluoro-2-halogeno-chinolin | |
| DE1695804C3 (de) | N Acyl 2 methyl 3 lndolylcarbon sauren, Verfahren zu ihrer Herstellung und Arzneimittel | |
| AT375925B (de) | Verfahren zur herstellung von neuen carbostyrilderivaten | |
| EP0004322A1 (de) | Isochinolinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Arzneimitteln | |
| DE889446C (de) | Verfahren zur Herstellung von Phenanthrolin-5, 6-chinonen | |
| DE1252204B (de) | Verfahren zur Herstellung von 2,4-Dinitropyrrolderivaten | |
| CH578535A5 (en) | Quinoline-3-carboxylic acid derivs - with e.g. analgesic, antinociceptive, antiinflammatory and antiallergic props | |
| DE2518999A1 (de) | Verfahren zur herstellung von sulfamylbenzoesaeuren | |
| AT376209B (de) | Verfahren zur herstellung von neuen carbostyrilderivaten | |
| DE69422495T2 (de) | Chinolondisulfide als zwischenverbindungen | |
| AT344153B (de) | Verfahren zur herstellung neuer 2-alkyl-5-indanessigsaeure- und -alkylester-derivate | |
| DE1543221C (de) | Verfahren zur Herstellung von tetracyclischen Verbindungen | |
| AT268321B (de) | Verfahren zur Herstellung von neuen heterocyclischen Verbindungen und ihren Salzen | |
| AT366673B (de) | Verfahren zur herstellung neuer phthalazin-4ylessigs[uren und deren salze | |
| DE2165310A1 (de) | Neue 1-aryl-3,4-dihydro-(2h,5h)-1,4benzodiazepin-5-one und verfahren zu ihrer herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8140 | Disposal/non-payment of the annual fee for main application |