CH639374A5 - N-(4-pyrazolidinyl)-benzamides, presentant notamment des proprietes antiemetiques et de vidage gastrique. - Google Patents
N-(4-pyrazolidinyl)-benzamides, presentant notamment des proprietes antiemetiques et de vidage gastrique. Download PDFInfo
- Publication number
- CH639374A5 CH639374A5 CH867478A CH867478A CH639374A5 CH 639374 A5 CH639374 A5 CH 639374A5 CH 867478 A CH867478 A CH 867478A CH 867478 A CH867478 A CH 867478A CH 639374 A5 CH639374 A5 CH 639374A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- pyrazolidinyl
- chloro
- amino
- chloride
- Prior art date
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- -1 4-PYRAZOLIDINYL Chemical class 0.000 title claims description 10
- 230000030136 gastric emptying Effects 0.000 title description 9
- 230000003474 anti-emetic effect Effects 0.000 title description 8
- 239000002111 antiemetic agent Substances 0.000 title description 6
- 229940054066 benzamide antipsychotics Drugs 0.000 title description 5
- 239000000203 mixture Substances 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- PVVXYTUJPSAUPX-UHFFFAOYSA-N 4-chloro-n-(1,2-dimethylpyrazolidin-4-yl)-n-phenylbenzamide Chemical compound C1N(C)N(C)CC1N(C=1C=CC=CC=1)C(=O)C1=CC=C(Cl)C=C1 PVVXYTUJPSAUPX-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- YFXIKEZOBJFVAQ-UHFFFAOYSA-N dazopride Chemical compound C1N(CC)N(CC)CC1NC(=O)C1=CC(Cl)=C(N)C=C1OC YFXIKEZOBJFVAQ-UHFFFAOYSA-N 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
- DXSUWXAMHYCUFF-UHFFFAOYSA-N n-(1,2-diethylpyrazolidin-4-yl)-4-fluorobenzamide Chemical compound C1N(CC)N(CC)CC1NC(=O)C1=CC=C(F)C=C1 DXSUWXAMHYCUFF-UHFFFAOYSA-N 0.000 claims description 2
- BBDOMHXDXUDXPB-UHFFFAOYSA-N n-pyrazolidin-4-ylbenzamide Chemical class C=1C=CC=CC=1C(=O)NC1CNNC1 BBDOMHXDXUDXPB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- MWKPHEKRHBZGIV-UHFFFAOYSA-N pyrazolidin-4-amine Chemical compound NC1CNNC1 MWKPHEKRHBZGIV-UHFFFAOYSA-N 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 58
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 239000000243 solution Substances 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 210000002784 stomach Anatomy 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 235000012054 meals Nutrition 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- RVEATKYEARPWRE-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxybenzoic acid Chemical compound COC1=CC(N)=C(Cl)C=C1C(O)=O RVEATKYEARPWRE-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 206010047700 Vomiting Diseases 0.000 description 4
- 150000003936 benzamides Chemical class 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 230000008673 vomiting Effects 0.000 description 4
- FQWUIOJVBDSHQH-UHFFFAOYSA-N 1,2-diethylpyrazolidin-4-amine Chemical compound CCN1CC(N)CN1CC FQWUIOJVBDSHQH-UHFFFAOYSA-N 0.000 description 3
- ZAOBFIURDGPCBP-UHFFFAOYSA-N 1,2-dimethylpyrazolidin-4-amine Chemical compound CN1CC(N)CN1C ZAOBFIURDGPCBP-UHFFFAOYSA-N 0.000 description 3
- NSHLYLMEOSXOCW-UHFFFAOYSA-N 1-methyl-2-propan-2-ylpyrazolidin-4-amine Chemical compound CC(C)N1CC(N)CN1C NSHLYLMEOSXOCW-UHFFFAOYSA-N 0.000 description 3
- FBKMPHZLJCLLSG-UHFFFAOYSA-N 4-chloro-1,2-diethylpyrazolidine Chemical compound CCN1CC(Cl)CN1CC FBKMPHZLJCLLSG-UHFFFAOYSA-N 0.000 description 3
- 241000220479 Acacia Species 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 239000002026 chloroform extract Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- WMIFNZMQNGQGDW-BTJKTKAUSA-N (z)-but-2-enedioic acid;2-(1,2-diethylpyrazolidin-4-yl)isoindole-1,3-dione Chemical compound OC(=O)\C=C/C(O)=O.C1N(CC)N(CC)CC1N1C(=O)C2=CC=CC=C2C1=O WMIFNZMQNGQGDW-BTJKTKAUSA-N 0.000 description 2
- UXILCSZJNQSVKU-UHFFFAOYSA-N 1,2-diethylpyrazolidin-4-ol Chemical compound CCN1CC(O)CN1CC UXILCSZJNQSVKU-UHFFFAOYSA-N 0.000 description 2
- NNRDMDHLPHFDSE-UHFFFAOYSA-N 1-benzyl-2-methylpyrazolidin-4-amine Chemical compound CN1CC(N)CN1CC1=CC=CC=C1 NNRDMDHLPHFDSE-UHFFFAOYSA-N 0.000 description 2
- XYUOOPRAZMJZIY-UHFFFAOYSA-N 1-cyclohexyl-2-methylpyrazolidin-4-amine Chemical compound CN1CC(N)CN1C1CCCCC1 XYUOOPRAZMJZIY-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- XFZMCFJADJFEBB-UHFFFAOYSA-N 2-methoxy-5-sulfamoylbenzoyl chloride Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(Cl)=O XFZMCFJADJFEBB-UHFFFAOYSA-N 0.000 description 2
- BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 2
- RUJYJCANMOTJMO-UHFFFAOYSA-N 3-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=CC(C(Cl)=O)=C1 RUJYJCANMOTJMO-UHFFFAOYSA-N 0.000 description 2
- USEDMAWWQDFMFY-UHFFFAOYSA-N 4-cyanobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(C#N)C=C1 USEDMAWWQDFMFY-UHFFFAOYSA-N 0.000 description 2
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- VFPGZYSBOACGQT-UHFFFAOYSA-N 5-chloro-3-fluoro-2-methoxybenzoyl chloride Chemical compound COC1=C(C(=O)Cl)C=C(C=C1F)Cl VFPGZYSBOACGQT-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000007903 gelatin capsule Substances 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
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- BLLUKFLDXGWKIO-WLHGVMLRSA-N (e)-but-2-enedioic acid;1-cyclohexyl-2-methylpyrazolidin-4-amine Chemical compound OC(=O)\C=C\C(O)=O.CN1CC(N)CN1C1CCCCC1 BLLUKFLDXGWKIO-WLHGVMLRSA-N 0.000 description 1
- YJDFPCJSLMKJBY-UHFFFAOYSA-N 1,2-diethyl-n-methylpyrazolidin-4-amine Chemical compound CCN1CC(NC)CN1CC YJDFPCJSLMKJBY-UHFFFAOYSA-N 0.000 description 1
- OBZCWJDSKOLWKQ-UHFFFAOYSA-N 1,2-diethyl-n-phenylpyrazolidin-4-amine Chemical compound C1N(CC)N(CC)CC1NC1=CC=CC=C1 OBZCWJDSKOLWKQ-UHFFFAOYSA-N 0.000 description 1
- YUCYGMWSUUTFOK-UHFFFAOYSA-N 1,2-dimethyl-n-phenylpyrazolidin-4-amine Chemical compound C1N(C)N(C)CC1NC1=CC=CC=C1 YUCYGMWSUUTFOK-UHFFFAOYSA-N 0.000 description 1
- HMQFUSFGZAPMEH-UHFFFAOYSA-N 1,2-dimethylpyrazolidin-4-ol Chemical compound CN1CC(O)CN1C HMQFUSFGZAPMEH-UHFFFAOYSA-N 0.000 description 1
- KVIUXRJCBBXEGJ-UHFFFAOYSA-N 2,4-dimethoxybenzoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C(OC)=C1 KVIUXRJCBBXEGJ-UHFFFAOYSA-N 0.000 description 1
- RAAGZOYMEQDCTD-UHFFFAOYSA-N 2-fluorobenzoyl chloride Chemical compound FC1=CC=CC=C1C(Cl)=O RAAGZOYMEQDCTD-UHFFFAOYSA-N 0.000 description 1
- DJDAPLBWGIXUAG-UHFFFAOYSA-N 2-methoxy-4-nitrobenzoyl chloride Chemical compound COC1=CC([N+]([O-])=O)=CC=C1C(Cl)=O DJDAPLBWGIXUAG-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- VTXNOVCTHUBABW-UHFFFAOYSA-N 3,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C(Cl)=C1 VTXNOVCTHUBABW-UHFFFAOYSA-N 0.000 description 1
- CFNNQXOPPGQFHV-UHFFFAOYSA-N 3,4-diethoxybenzoyl chloride Chemical compound CCOC1=CC=C(C(Cl)=O)C=C1OCC CFNNQXOPPGQFHV-UHFFFAOYSA-N 0.000 description 1
- NNOHXABAQAGKRZ-UHFFFAOYSA-N 3,5-dinitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(C(Cl)=O)=CC([N+]([O-])=O)=C1 NNOHXABAQAGKRZ-UHFFFAOYSA-N 0.000 description 1
- ZHRJFQNKKKUBFY-UHFFFAOYSA-N 3-acetamido-2-methoxy-5-(trifluoromethyl)benzoyl chloride Chemical compound COC1=C(NC(C)=O)C=C(C(F)(F)F)C=C1C(Cl)=O ZHRJFQNKKKUBFY-UHFFFAOYSA-N 0.000 description 1
- PBOOZQFGWNZNQE-UHFFFAOYSA-N 3-bromobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(Br)=C1 PBOOZQFGWNZNQE-UHFFFAOYSA-N 0.000 description 1
- VIBQMHMFEQVLSL-UHFFFAOYSA-N 4-(dimethylamino)-2-methoxybenzoyl chloride Chemical compound COC1=CC(N(C)C)=CC=C1C(Cl)=O VIBQMHMFEQVLSL-UHFFFAOYSA-N 0.000 description 1
- GOXCIWMHHSVOKW-UHFFFAOYSA-N 4-acetamido-5-chloro-2-methoxybenzoic acid Chemical compound COC1=CC(NC(C)=O)=C(Cl)C=C1C(O)=O GOXCIWMHHSVOKW-UHFFFAOYSA-N 0.000 description 1
- KRKXGCJUNKZXOY-UHFFFAOYSA-N 4-acetamidobenzoyl chloride Chemical compound CC(=O)NC1=CC=C(C(Cl)=O)C=C1 KRKXGCJUNKZXOY-UHFFFAOYSA-N 0.000 description 1
- HIUOCIJUFCZOGD-UHFFFAOYSA-N 4-amino-5-chloro-n-(1,2-dimethylpyrazolidin-4-yl)-2-methoxybenzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NC1CN(C)N(C)C1 HIUOCIJUFCZOGD-UHFFFAOYSA-N 0.000 description 1
- QYEFGQXADUQZAQ-UHFFFAOYSA-N 4-amino-n-(1,2-diethylpyrazolidin-4-yl)benzamide Chemical compound C1N(CC)N(CC)CC1NC(=O)C1=CC=C(N)C=C1 QYEFGQXADUQZAQ-UHFFFAOYSA-N 0.000 description 1
- UWKMBCBEXCDRCF-UHFFFAOYSA-N 4-bromo-2-ethoxybenzoyl chloride Chemical compound CCOC1=CC(Br)=CC=C1C(Cl)=O UWKMBCBEXCDRCF-UHFFFAOYSA-N 0.000 description 1
- DENKGPBHLYFNGK-UHFFFAOYSA-N 4-bromobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Br)C=C1 DENKGPBHLYFNGK-UHFFFAOYSA-N 0.000 description 1
- KMGCTFHTBKBITO-UHFFFAOYSA-N 4-butoxybenzoyl chloride Chemical compound CCCCOC1=CC=C(C(Cl)=O)C=C1 KMGCTFHTBKBITO-UHFFFAOYSA-N 0.000 description 1
- QNOOQQCTAPGUOV-UHFFFAOYSA-N 4-chloro-1,2-dimethylpyrazolidine Chemical compound CN1CC(Cl)CN1C QNOOQQCTAPGUOV-UHFFFAOYSA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 1
- 229940125683 antiemetic agent Drugs 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000037396 body weight Effects 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229940074045 glyceryl distearate Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000002350 laparotomy Methods 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- UMLAHDOXQOXXHI-UHFFFAOYSA-N n-(1,2-diethylpyrazolidin-4-yl)-4-nitrobenzamide Chemical compound C1N(CC)N(CC)CC1NC(=O)C1=CC=C([N+]([O-])=O)C=C1 UMLAHDOXQOXXHI-UHFFFAOYSA-N 0.000 description 1
- RQSJNVZNAHLTMO-UHFFFAOYSA-N n-(1,2-diethylpyrazolidin-4-yl)-4-nitrobenzamide;hydrochloride Chemical compound Cl.C1N(CC)N(CC)CC1NC(=O)C1=CC=C([N+]([O-])=O)C=C1 RQSJNVZNAHLTMO-UHFFFAOYSA-N 0.000 description 1
- AZFCGJAMJPNIAU-UHFFFAOYSA-N n-(1,2-dimethylpyrazolidin-4-yl)-3,4,5-trimethoxybenzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NC2CN(C)N(C)C2)=C1 AZFCGJAMJPNIAU-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000013223 sprague-dawley female rat Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 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
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/04—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Hospice & Palliative Care (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Otolaryngology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82603177A | 1977-08-19 | 1977-08-19 | |
| US90036978A | 1978-04-26 | 1978-04-26 | |
| US93012578A | 1978-08-01 | 1978-08-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH639374A5 true CH639374A5 (fr) | 1983-11-15 |
Family
ID=27420183
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH867478A CH639374A5 (fr) | 1977-08-19 | 1978-08-15 | N-(4-pyrazolidinyl)-benzamides, presentant notamment des proprietes antiemetiques et de vidage gastrique. |
| CH228983A CH645356A5 (fr) | 1977-08-19 | 1983-04-28 | 4-aminopyrazolidines. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH228983A CH645356A5 (fr) | 1977-08-19 | 1983-04-28 | 4-aminopyrazolidines. |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5441873A (en17) |
| AU (1) | AU521421B2 (en17) |
| BR (1) | BR7805288A (en17) |
| CA (1) | CA1105037A (en17) |
| CH (2) | CH639374A5 (en17) |
| DE (1) | DE2836062A1 (en17) |
| DK (1) | DK152361C (en17) |
| ES (1) | ES472686A1 (en17) |
| FI (1) | FI68044C (en17) |
| FR (1) | FR2400511A1 (en17) |
| GB (2) | GB2003153B (en17) |
| HK (1) | HK42282A (en17) |
| IE (1) | IE47430B1 (en17) |
| MX (1) | MX5469E (en17) |
| NL (1) | NL7808596A (en17) |
| NO (1) | NO149107C (en17) |
| NZ (1) | NZ188189A (en17) |
| PH (1) | PH13331A (en17) |
| PT (1) | PT68442A (en17) |
| SE (2) | SE444434B (en17) |
| YU (1) | YU41116B (en17) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4309552A (en) * | 1980-08-07 | 1982-01-05 | A. H. Robins Company, Inc. | Synthesis of 4-nitro-1,2-hydrocarbyl pyrazolidines and process for preparation thereof |
| US5126343A (en) * | 1989-09-11 | 1992-06-30 | G. D. Searle & Co. | N-azabicyclo [3.3.0]octane amides of aromatic acids |
| JP3065506B2 (ja) * | 1995-04-03 | 2000-07-17 | 株式会社資生堂 | ピラゾリジン誘導体及びラジカルスカベンジャー、脳梗塞抑制剤、脳浮腫抑制剤 |
| AR086587A1 (es) | 2011-05-31 | 2014-01-08 | Syngenta Participations Ag | Compuestos insecticidas |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3966957A (en) * | 1972-04-03 | 1976-06-29 | A. H. Robins Company, Incorporated | Method for controlling emesis with N-(1-substituted-3-pyrrolidinyl)benzamides and thiobenzamides |
-
1976
- 1976-08-14 PH PH21489A patent/PH13331A/en unknown
-
1978
- 1978-08-15 CH CH867478A patent/CH639374A5/fr not_active IP Right Cessation
- 1978-08-16 FI FI782507A patent/FI68044C/fi not_active IP Right Cessation
- 1978-08-16 SE SE7808694A patent/SE444434B/sv not_active IP Right Cessation
- 1978-08-17 GB GB7833696A patent/GB2003153B/en not_active Expired
- 1978-08-17 BR BR7805288A patent/BR7805288A/pt unknown
- 1978-08-17 DE DE19782836062 patent/DE2836062A1/de not_active Withdrawn
- 1978-08-17 GB GB7901821A patent/GB2017678B/en not_active Expired
- 1978-08-18 IE IE1682/78A patent/IE47430B1/en unknown
- 1978-08-18 NZ NZ188189A patent/NZ188189A/en unknown
- 1978-08-18 PT PT68442A patent/PT68442A/pt unknown
- 1978-08-18 MX MX787322U patent/MX5469E/es unknown
- 1978-08-18 DK DK366978A patent/DK152361C/da not_active IP Right Cessation
- 1978-08-18 NL NL7808596A patent/NL7808596A/xx not_active Application Discontinuation
- 1978-08-18 YU YU1986/78A patent/YU41116B/xx unknown
- 1978-08-18 CA CA309,651A patent/CA1105037A/en not_active Expired
- 1978-08-18 FR FR7824138A patent/FR2400511A1/fr active Granted
- 1978-08-18 NO NO782812A patent/NO149107C/no unknown
- 1978-08-18 AU AU39061/78A patent/AU521421B2/en not_active Expired
- 1978-08-18 ES ES472686A patent/ES472686A1/es not_active Expired
- 1978-08-19 JP JP10136878A patent/JPS5441873A/ja active Granted
-
1982
- 1982-09-30 HK HK422/82A patent/HK42282A/xx unknown
-
1983
- 1983-04-28 CH CH228983A patent/CH645356A5/fr not_active IP Right Cessation
- 1983-06-21 SE SE8303564A patent/SE451723B/sv not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |