NO870053L - Fremgangsmaate for fremstilling av terapeutisk aktive nitrogenholdige, kondenserte, aromatiske forbindelser. - Google Patents
Fremgangsmaate for fremstilling av terapeutisk aktive nitrogenholdige, kondenserte, aromatiske forbindelser.Info
- Publication number
- NO870053L NO870053L NO870053A NO870053A NO870053L NO 870053 L NO870053 L NO 870053L NO 870053 A NO870053 A NO 870053A NO 870053 A NO870053 A NO 870053A NO 870053 L NO870053 L NO 870053L
- Authority
- NO
- Norway
- Prior art keywords
- compound
- formula
- salt
- carbonylmethyl
- piperazinyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 52
- 238000002360 preparation method Methods 0.000 title claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title 2
- 150000001491 aromatic compounds Chemical class 0.000 title 1
- 229910052757 nitrogen Inorganic materials 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 102
- 150000003839 salts Chemical class 0.000 claims description 68
- -1 nitroso, amidino Chemical group 0.000 claims description 46
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- DRVCULVBWNEGTA-UHFFFAOYSA-N 3-[2-(4-aminopiperazin-1-yl)-2-oxoethyl]-5-chloro-1,3-benzothiazol-2-one Chemical compound C1CN(N)CCN1C(=O)CN1C(=O)SC2=CC=C(Cl)C=C21 DRVCULVBWNEGTA-UHFFFAOYSA-N 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001118 alkylidene group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000783 acetimidoyl group Chemical group C(C)(=N)* 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000003435 aroyl group Chemical group 0.000 claims description 2
- 125000005116 aryl carbamoyl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 238000007034 nitrosation reaction Methods 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 3
- 239000005977 Ethylene Substances 0.000 claims 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- QFHMNFAUXJAINK-UHFFFAOYSA-N [1-(carbamoylamino)-2-methylpropyl]urea Chemical group NC(=O)NC(C(C)C)NC(N)=O QFHMNFAUXJAINK-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 83
- 238000002844 melting Methods 0.000 description 74
- 230000008018 melting Effects 0.000 description 74
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 62
- 238000006243 chemical reaction Methods 0.000 description 58
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 57
- 239000000203 mixture Substances 0.000 description 55
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
- 239000002585 base Substances 0.000 description 48
- 239000000243 solution Substances 0.000 description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- 238000004458 analytical method Methods 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 238000000921 elemental analysis Methods 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 20
- 235000011054 acetic acid Nutrition 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- 238000001816 cooling Methods 0.000 description 15
- 239000013078 crystal Substances 0.000 description 15
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 15
- 238000012360 testing method Methods 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 10
- BIMFMUNOCZIOAP-UHFFFAOYSA-N 3-[2-(4-aminopiperazin-1-yl)-2-oxoethyl]-5-chloro-1,3-benzothiazol-2-one;hydrochloride Chemical compound Cl.C1CN(N)CCN1C(=O)CN1C(=O)SC2=CC=C(Cl)C=C21 BIMFMUNOCZIOAP-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000002391 heterocyclic compounds Chemical class 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 7
- 239000003638 chemical reducing agent Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 238000006722 reduction reaction Methods 0.000 description 7
- 230000007306 turnover Effects 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 230000002411 adverse Effects 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000002198 insoluble material Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 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 4
- 102000008186 Collagen Human genes 0.000 description 4
- 108010035532 Collagen Proteins 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 229920001436 collagen Polymers 0.000 description 4
- 210000002683 foot Anatomy 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- AOKCUAFRZCTWLL-UHFFFAOYSA-N 1-(4-aminopiperazin-1-yl)-2-(6-chloro-2-imino-1,3-benzothiazol-3-yl)ethanone Chemical compound C1CN(N)CCN1C(=O)CN1C(=N)SC2=CC(Cl)=CC=C21 AOKCUAFRZCTWLL-UHFFFAOYSA-N 0.000 description 3
- WPOIOEAYDBUGKI-UHFFFAOYSA-N 1-[2-(4-aminopiperazin-1-yl)-2-oxoethyl]-6-chloro-[1,3]thiazolo[5,4-b]pyridin-2-one;hydrochloride Chemical compound Cl.C1CN(N)CCN1C(=O)CN1C(=O)SC2=NC=C(Cl)C=C21 WPOIOEAYDBUGKI-UHFFFAOYSA-N 0.000 description 3
- SYPHZHWTISIDEQ-UHFFFAOYSA-N 1-[2-[4-(benzylideneamino)piperazin-1-yl]-2-oxoethyl]-6-chloroindole-2,3-dione Chemical compound C12=CC(Cl)=CC=C2C(=O)C(=O)N1CC(=O)N(CC1)CCN1N=CC1=CC=CC=C1 SYPHZHWTISIDEQ-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- FVZULXGCDWRZIK-UHFFFAOYSA-N 3-[2-(4-amino-1,4-diazepan-1-yl)-2-oxoethyl]-5-chloro-1,3-benzothiazol-2-one;hydrochloride Chemical compound Cl.C1CN(N)CCCN1C(=O)CN1C(=O)SC2=CC=C(Cl)C=C21 FVZULXGCDWRZIK-UHFFFAOYSA-N 0.000 description 3
- KXFAHCWJYHYOAI-UHFFFAOYSA-N 3-[2-(4-amino-3-methylpiperazin-1-yl)-2-oxoethyl]-5-chloro-1,3-benzothiazol-2-one;hydrochloride Chemical compound Cl.C1CN(N)C(C)CN1C(=O)CN1C(=O)SC2=CC=C(Cl)C=C21 KXFAHCWJYHYOAI-UHFFFAOYSA-N 0.000 description 3
- HSKNLOJEZTXYTP-UHFFFAOYSA-N 3-[2-(4-aminopiperazin-1-yl)-2-oxoethyl]-1,3-benzothiazol-2-one;hydrochloride Chemical compound Cl.C1CN(N)CCN1C(=O)CN1C(=O)SC2=CC=CC=C21 HSKNLOJEZTXYTP-UHFFFAOYSA-N 0.000 description 3
- OOPYTJRZJHGIHZ-UHFFFAOYSA-N 3-[2-(4-aminopiperazin-1-yl)-2-oxoethyl]-4-chloro-1,3-benzothiazol-2-one;hydrochloride Chemical compound Cl.C1CN(N)CCN1C(=O)CN1C(=O)SC2=CC=CC(Cl)=C21 OOPYTJRZJHGIHZ-UHFFFAOYSA-N 0.000 description 3
- AAALPAIGUUQZEU-UHFFFAOYSA-N 3-[2-(4-aminopiperazin-1-yl)-2-oxoethyl]-5-(trifluoromethyl)-1,3-benzothiazol-2-one;hydrochloride Chemical compound Cl.C1CN(N)CCN1C(=O)CN1C(=O)SC2=CC=C(C(F)(F)F)C=C21 AAALPAIGUUQZEU-UHFFFAOYSA-N 0.000 description 3
- ODZPJYIJUIJRQV-UHFFFAOYSA-N 3-[2-(4-aminopiperazin-1-yl)-2-oxoethyl]-5-chloro-1,3-benzoxazol-2-one;hydrochloride Chemical compound Cl.C1CN(N)CCN1C(=O)CN1C(=O)OC2=CC=C(Cl)C=C21 ODZPJYIJUIJRQV-UHFFFAOYSA-N 0.000 description 3
- HLJWDRJVVMDLOY-UHFFFAOYSA-N 3-[2-(4-aminopiperazin-1-yl)-2-oxoethyl]-5-chloro-6-phenyl-1,3-benzothiazol-2-one;hydrochloride Chemical compound Cl.C1CN(N)CCN1C(=O)CN1C(=O)SC2=CC(C=3C=CC=CC=3)=C(Cl)C=C21 HLJWDRJVVMDLOY-UHFFFAOYSA-N 0.000 description 3
- CWPKMUHXFMZSMD-UHFFFAOYSA-N 3-[2-(4-aminopiperazin-1-yl)-2-oxoethyl]-5-methyl-1,3-benzothiazol-2-one;hydrochloride Chemical compound Cl.C12=CC(C)=CC=C2SC(=O)N1CC(=O)N1CCN(N)CC1 CWPKMUHXFMZSMD-UHFFFAOYSA-N 0.000 description 3
- XENZIJZRAZBQOY-UHFFFAOYSA-N 3-[2-(4-aminopiperazin-1-yl)-2-oxoethyl]-6-bromo-5-chloro-1,3-benzothiazol-2-one;hydrochloride Chemical compound Cl.C1CN(N)CCN1C(=O)CN1C(=O)SC2=CC(Br)=C(Cl)C=C21 XENZIJZRAZBQOY-UHFFFAOYSA-N 0.000 description 3
- MVVRQZRGJNMSOV-UHFFFAOYSA-N 3-[2-(4-aminopiperazin-1-yl)-2-oxoethyl]-6-chloro-1,3-benzothiazol-2-one;hydrochloride Chemical compound Cl.C1CN(N)CCN1C(=O)CN1C(=O)SC2=CC(Cl)=CC=C21 MVVRQZRGJNMSOV-UHFFFAOYSA-N 0.000 description 3
- QNZMCUUXLSIRRL-UHFFFAOYSA-N 3-[2-(4-aminopiperazin-1-yl)-2-oxoethyl]-6-nitro-1,3-benzothiazol-2-one;hydrochloride Chemical compound Cl.C1CN(N)CCN1C(=O)CN1C(=O)SC2=CC([N+]([O-])=O)=CC=C21 QNZMCUUXLSIRRL-UHFFFAOYSA-N 0.000 description 3
- RCUIFZRHMYOBSH-UHFFFAOYSA-N 3-[2-(4-aminopiperazin-1-yl)-2-oxoethyl]-7-chloro-1,3-benzothiazol-2-one;hydrochloride Chemical compound Cl.C1CN(N)CCN1C(=O)CN1C(=O)SC2=C(Cl)C=CC=C21 RCUIFZRHMYOBSH-UHFFFAOYSA-N 0.000 description 3
- VDMDBQXVWYVRNF-UHFFFAOYSA-N 3-[2-(4-nitrosopiperazin-1-yl)-2-oxoethyl]-1,3-benzothiazol-2-one Chemical compound C1CN(N=O)CCN1C(=O)CN1C(=O)SC2=CC=CC=C21 VDMDBQXVWYVRNF-UHFFFAOYSA-N 0.000 description 3
- ZWVSOMADXSYSHM-UHFFFAOYSA-N 3-[2-[4-(benzylideneamino)piperazin-1-yl]-2-oxoethyl]-5-chloro-1,3-benzothiazol-2-one Chemical compound C12=CC(Cl)=CC=C2SC(=O)N1CC(=O)N(CC1)CCN1N=CC1=CC=CC=C1 ZWVSOMADXSYSHM-UHFFFAOYSA-N 0.000 description 3
- DNORVVNABISTJJ-UHFFFAOYSA-N 5-chloro-3-[2-(4-nitrosopiperazin-1-yl)-2-oxoethyl]-1,3-benzothiazol-2-one Chemical compound C12=CC(Cl)=CC=C2SC(=O)N1CC(=O)N1CCN(N=O)CC1 DNORVVNABISTJJ-UHFFFAOYSA-N 0.000 description 3
- CXSVYEGSHMLTLL-UHFFFAOYSA-N 5-chloro-3-[2-[4-(2-methylpropylideneamino)piperazin-1-yl]-2-oxoethyl]-1,3-benzothiazol-2-one Chemical compound C1CN(N=CC(C)C)CCN1C(=O)CN1C(=O)SC2=CC=C(Cl)C=C21 CXSVYEGSHMLTLL-UHFFFAOYSA-N 0.000 description 3
- JQNQHJCDBPGYDV-UHFFFAOYSA-N 6-chloro-1-[2-(4-nitrosopiperazin-1-yl)-2-oxoethyl]-[1,3]thiazolo[5,4-b]pyridin-2-one Chemical compound C12=CC(Cl)=CN=C2SC(=O)N1CC(=O)N1CCN(N=O)CC1 JQNQHJCDBPGYDV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- PIEPQKCYPFFYMG-UHFFFAOYSA-N tris acetate Chemical compound CC(O)=O.OCC(N)(CO)CO PIEPQKCYPFFYMG-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/40—Nitrogen atoms, not forming part of a nitro radical, e.g. isatin semicarbazone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB868601160A GB8601160D0 (en) | 1986-01-17 | 1986-01-17 | Heterocyclic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO870053D0 NO870053D0 (no) | 1987-01-06 |
| NO870053L true NO870053L (no) | 1987-07-20 |
Family
ID=10591560
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO870053A NO870053L (no) | 1986-01-17 | 1987-01-06 | Fremgangsmaate for fremstilling av terapeutisk aktive nitrogenholdige, kondenserte, aromatiske forbindelser. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4797399A (fr) |
| EP (1) | EP0232740A1 (fr) |
| JP (1) | JPS62181253A (fr) |
| KR (1) | KR870007163A (fr) |
| CN (1) | CN87100707A (fr) |
| AU (1) | AU6762687A (fr) |
| DK (1) | DK8687A (fr) |
| FI (1) | FI865369A (fr) |
| GB (1) | GB8601160D0 (fr) |
| IL (1) | IL81172A0 (fr) |
| NO (1) | NO870053L (fr) |
| OA (1) | OA08462A (fr) |
| PT (1) | PT84103A (fr) |
| ZA (1) | ZA869748B (fr) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2601366B1 (fr) * | 1986-07-10 | 1988-11-25 | Andre Buzas | Derives de la benzhydryloxyethyl-piperazine, procedes d'obtention et de compositions pharmaceutiques les contenant. |
| GB8714596D0 (en) * | 1987-06-22 | 1987-07-29 | Fujisawa Pharmaceutical Co | Thiazolopyridine compounds |
| FI95572C (fi) | 1987-06-22 | 1996-02-26 | Eisai Co Ltd | Menetelmä lääkeaineena käyttökelpoisen piperidiinijohdannaisten tai sen farmaseuttisen suolan valmistamiseksi |
| FR2663929A1 (fr) * | 1990-06-29 | 1992-01-03 | Adir | Nouveaux derives d'oxazolo pyridines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2669336B1 (fr) * | 1990-11-20 | 1993-01-22 | Adir | Nouveaux derives d'oxazolo pyridines, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent. |
| IT1251144B (it) * | 1991-07-30 | 1995-05-04 | Boehringer Ingelheim Italia | Derivati del benzimidazolone |
| IL115420A0 (en) | 1994-09-26 | 1995-12-31 | Zeneca Ltd | Aminoheterocyclic derivatives |
| EP0880501A1 (fr) | 1996-02-02 | 1998-12-02 | Zeneca Limited | Composes heterocycliques utiles en tant qu'agents pharmaceutiques |
| GB9602294D0 (en) * | 1996-02-05 | 1996-04-03 | Zeneca Ltd | Heterocyclic compounds |
| DE19618999A1 (de) * | 1996-05-10 | 1997-11-13 | Klinge Co Chem Pharm Fab | Neue Benzothiazolinone |
| DE19618970A1 (de) * | 1996-05-10 | 1997-11-13 | Klinge Co Chem Pharm Fab | Neue Thiazolopyridine |
| PL331599A1 (en) * | 1996-08-14 | 1999-08-02 | Zeneca Ltd | Substituted derivatives of pyrimidine and their pharmaceutical application |
| UA56197C2 (uk) | 1996-11-08 | 2003-05-15 | Зенека Лімітед | Гетероциклічні похідні |
| JP2001511798A (ja) | 1997-02-13 | 2001-08-14 | ゼネカ・リミテッド | オキシド−スクアレンシクラーゼ抑制剤として有用な複素環化合物 |
| AU5999798A (en) | 1997-02-13 | 1998-09-08 | Zeneca Limited | Heterocyclic compounds useful as oxido-squalene cyclase inhibitors |
| HUP0100179A3 (en) | 1997-07-03 | 2002-12-28 | Bristol Myers Squibb Pharma Co | Imidazopyrimidine and imidazopyridine derivatives and pharmaceutical compositions thereof |
| GB9715895D0 (en) | 1997-07-29 | 1997-10-01 | Zeneca Ltd | Heterocyclic compounds |
| CN1109025C (zh) * | 1997-10-09 | 2003-05-21 | 藤泽药品工业株式会社 | 氨基哌嗪衍生物的新制造法 |
| US6124463A (en) * | 1998-07-02 | 2000-09-26 | Dupont Pharmaceuticals | Benzimidazoles as corticotropin release factor antagonists |
| US6365589B1 (en) | 1998-07-02 | 2002-04-02 | Bristol-Myers Squibb Pharma Company | Imidazo-pyridines, -pyridazines, and -triazines as corticotropin releasing factor antagonists |
| GB9902989D0 (en) | 1999-02-11 | 1999-03-31 | Zeneca Ltd | Heterocyclic derivatives |
| AU7887501A (en) * | 2000-07-06 | 2002-01-21 | Us Gov Health & Human Serv | Tetrahydrobenzothiazole analogues as neuroprotective agents |
| US7183410B2 (en) * | 2001-08-02 | 2007-02-27 | Bidachem S.P.A. | Stable polymorph of flibanserin |
| US20030060475A1 (en) * | 2001-08-10 | 2003-03-27 | Boehringer Ingelheim Pharma Kg | Method of using flibanserin for neuroprotection |
| UA78974C2 (en) | 2001-10-20 | 2007-05-10 | Boehringer Ingelheim Pharma | Use of flibanserin for treating disorders of sexual desire |
| US10675280B2 (en) | 2001-10-20 | 2020-06-09 | Sprout Pharmaceuticals, Inc. | Treating sexual desire disorders with flibanserin |
| TW200508197A (en) * | 2003-03-31 | 2005-03-01 | Ucb Sa | Indolone-acetamide derivatives, processes for preparing them and their uses |
| EP1719761A4 (fr) * | 2004-02-23 | 2007-10-10 | Dainippon Sumitomo Pharma Co | Nouveau compose heterocyclique |
| US20050239798A1 (en) * | 2004-04-22 | 2005-10-27 | Boehringer Ingelheim Pharmaceuticals, Inc. | Method for the treatment of premenstrual and other female sexual disorders |
| RU2445095C2 (ru) * | 2004-04-22 | 2012-03-20 | Бёрингер Ингельхайм Интернациональ Гмбх | Новые фармацевтические композиции для лечения сексуальных расстройств |
| US20060025420A1 (en) * | 2004-07-30 | 2006-02-02 | Boehringer Ingelheimn International GmbH | Pharmaceutical compositions for the treatment of female sexual disorders |
| CA2576812A1 (fr) * | 2004-09-03 | 2006-03-09 | Boehringer Ingelheim International Gmbh | Methode de traitement du trouble de l'hyperactivite avec deficit de l'attention |
| EP1858516A1 (fr) * | 2005-03-04 | 2007-11-28 | Boehringer Ingelheim International GmbH | Compositions pharmaceutiques utiles dans le traitement et/ou la prevention de la depression |
| US20060199805A1 (en) * | 2005-03-04 | 2006-09-07 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions for the treatment and/or prevention of anxiety disorders |
| WO2006096439A2 (fr) * | 2005-03-04 | 2006-09-14 | Boehringer Ingelheim International Gmbh | Compositions pharmaceutiques destinees au traitement et/ou a la prevention de la schizophrenie et de maladies associees |
| EP1904182A2 (fr) * | 2005-05-06 | 2008-04-02 | Boehringer Ingelheim International GmbH | Methode de traitement de la toxicomanie avec flibanserine |
| EP1888071A1 (fr) * | 2005-05-19 | 2008-02-20 | Boehringer Ingelheim International GmbH | Procede pour le traitement de dysfonctionnements sexuels d origine medicamenteuse |
| EP1888070A1 (fr) * | 2005-05-19 | 2008-02-20 | Boehringer Ingelheim International GmbH | Procede pour le traitement de dysfonctionnements sexuels dus a des etats pathologiques |
| US8227476B2 (en) | 2005-08-03 | 2012-07-24 | Sprout Pharmaceuticals, Inc. | Use of flibanserin in the treatment of obesity |
| US7923449B2 (en) * | 2005-10-29 | 2011-04-12 | Boehringer Ingelheim International Gmbh | Benzimidazolone derivatives for the treatment of premenstrual and other female sexual disorders |
| US20070123540A1 (en) * | 2005-10-29 | 2007-05-31 | Angelo Ceci | Sexual desire enhancing medicaments comprising benzimidazolone derivatives |
| US20070105869A1 (en) * | 2005-11-08 | 2007-05-10 | Stephane Pollentier | Use of flibanserin for the treatment of pre-menopausal sexual desire disorders |
| AU2007247094B2 (en) * | 2006-05-09 | 2012-11-01 | Sprout Pharmaceuticals, Inc. | Use of flibanserin for the treatment of post-menopausal Sexual Desire Disorders |
| CA2654798C (fr) | 2006-06-30 | 2015-01-13 | Boehringer Ingelheim International Gmbh | Flibanserine dans le traitement de l'incontinence urinaire et des maladies associees |
| EP2043648A1 (fr) * | 2006-07-14 | 2009-04-08 | Boehringer Ingelheim International GmbH | Utilisation de flibansérine pour le traitement de troubles sexuels chez les femmes |
| CL2007002214A1 (es) * | 2006-08-14 | 2008-03-07 | Boehringer Ingelheim Int | Composicion farmaceutica en la forma de comprimido, donde al menos la longitud del comprimido en el estado anterior de la aplicacion es al menos 7/12 del diametro pilorico del paciente y despues de ingerirlo en estado alimentado, la longitud del comp |
| AU2007286288A1 (en) * | 2006-08-14 | 2008-02-21 | Boehringer Ingelheim International Gmbh | Formulations of flibanserin and method for manufacturing the same |
| WO2008022932A2 (fr) * | 2006-08-25 | 2008-02-28 | Boehringer Ingelheim International Gmbh | Système de libération contrôlée et procédé de préparation correspondant |
| US8686008B2 (en) * | 2007-08-16 | 2014-04-01 | The University Of Mississippi | Highly selective sigma receptor ligands |
| UY31335A1 (es) | 2007-09-12 | 2009-04-30 | Tratamiento de sintomas vasomotores |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA928296A (en) * | 1967-06-05 | 1973-06-12 | Umio Suminori | N-substituted and n, n-disubstituted aminocarbonylalkyl compounds and their production |
| GB1270841A (en) * | 1969-03-28 | 1972-04-19 | Fujisawa Pharmaceutical Co | Benzothiazoline derivatives |
| GR65270B (en) * | 1978-10-10 | 1980-07-31 | Fujisawa Pharmaceutical Co | Isatin derivatives and processes for the preparation thereof |
| US4279909A (en) * | 1980-02-13 | 1981-07-21 | Fujisawa Pharmaceutical Co., Ltd. | Antiallergic method |
| JPS6015276A (ja) * | 1983-07-04 | 1985-01-25 | Nissan Motor Co Ltd | 自動車組立工程における組付部品の仕様判別方法 |
| JPS6063972A (ja) * | 1983-09-17 | 1985-04-12 | Sumitomo Electric Ind Ltd | クライオスタツト |
-
1986
- 1986-01-17 GB GB868601160A patent/GB8601160D0/en active Pending
- 1986-12-23 US US06/945,853 patent/US4797399A/en not_active Expired - Fee Related
- 1986-12-29 ZA ZA869748A patent/ZA869748B/xx unknown
- 1986-12-31 FI FI865369A patent/FI865369A/fi not_active Application Discontinuation
-
1987
- 1987-01-05 IL IL81172A patent/IL81172A0/xx unknown
- 1987-01-06 NO NO870053A patent/NO870053L/no unknown
- 1987-01-08 DK DK008687A patent/DK8687A/da unknown
- 1987-01-14 PT PT84103A patent/PT84103A/pt unknown
- 1987-01-15 EP EP87100448A patent/EP0232740A1/fr not_active Withdrawn
- 1987-01-16 JP JP62008379A patent/JPS62181253A/ja active Pending
- 1987-01-16 AU AU67626/87A patent/AU6762687A/en not_active Abandoned
- 1987-01-16 OA OA59044A patent/OA08462A/fr unknown
- 1987-01-17 KR KR870000328A patent/KR870007163A/ko not_active Application Discontinuation
- 1987-01-17 CN CN198787100707A patent/CN87100707A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IL81172A0 (en) | 1987-08-31 |
| JPS62181253A (ja) | 1987-08-08 |
| EP0232740A1 (fr) | 1987-08-19 |
| KR870007163A (ko) | 1987-08-17 |
| DK8687A (da) | 1987-07-18 |
| AU6762687A (en) | 1987-07-23 |
| GB8601160D0 (en) | 1986-02-19 |
| FI865369A (fi) | 1987-07-18 |
| OA08462A (fr) | 1988-07-29 |
| PT84103A (en) | 1987-02-01 |
| US4797399A (en) | 1989-01-10 |
| DK8687D0 (da) | 1987-01-08 |
| CN87100707A (zh) | 1987-09-02 |
| FI865369A0 (fi) | 1986-12-31 |
| NO870053D0 (no) | 1987-01-06 |
| ZA869748B (en) | 1987-08-26 |
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