FI68044C - Foerfarande foer framstaellning av terapeutiskt aktiva n-(4-pyrazolidinyl)bensamider - Google Patents
Foerfarande foer framstaellning av terapeutiskt aktiva n-(4-pyrazolidinyl)bensamider Download PDFInfo
- Publication number
- FI68044C FI68044C FI782507A FI782507A FI68044C FI 68044 C FI68044 C FI 68044C FI 782507 A FI782507 A FI 782507A FI 782507 A FI782507 A FI 782507A FI 68044 C FI68044 C FI 68044C
- Authority
- FI
- Finland
- Prior art keywords
- amino
- formula
- substituted
- pyrazolidine
- pyrazolidinyl
- Prior art date
Links
- 230000001225 therapeutic effect Effects 0.000 title 2
- 230000004913 activation Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 9
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Chemical group 0.000 claims description 5
- BBDOMHXDXUDXPB-UHFFFAOYSA-N n-pyrazolidin-4-ylbenzamide Chemical class C=1C=CC=CC=1C(=O)NC1CNNC1 BBDOMHXDXUDXPB-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 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
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 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 description 3
- 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 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- UEWVYZWCMJCHRT-UHFFFAOYSA-N n-fluoronitramide Chemical group [O-][N+](=O)NF UEWVYZWCMJCHRT-UHFFFAOYSA-N 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 150000003218 pyrazolidines Chemical class 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 56
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 239000000243 solution Substances 0.000 description 30
- 239000000203 mixture Substances 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 7
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
- 210000002784 stomach Anatomy 0.000 description 6
- 230000003474 anti-emetic effect Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 241000700159 Rattus Species 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000002026 chloroform extract Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 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
- FBKMPHZLJCLLSG-UHFFFAOYSA-N 4-chloro-1,2-diethylpyrazolidine Chemical compound CCN1CC(Cl)CN1CC FBKMPHZLJCLLSG-UHFFFAOYSA-N 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 239000003929 acidic solution Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 239000002111 antiemetic agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000030136 gastric emptying Effects 0.000 description 3
- -1 nitro, amino Chemical group 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000010959 steel Substances 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
- 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 2
- 241000220479 Acacia Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- ILUJQPXNXACGAN-UHFFFAOYSA-N O-methylsalicylic acid Chemical compound COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000012074 organic phase 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
- 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
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent 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
- 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
- HMQFUSFGZAPMEH-UHFFFAOYSA-N 1,2-dimethylpyrazolidin-4-ol Chemical compound CN1CC(O)CN1C HMQFUSFGZAPMEH-UHFFFAOYSA-N 0.000 description 1
- NNRDMDHLPHFDSE-UHFFFAOYSA-N 1-benzyl-2-methylpyrazolidin-4-amine Chemical compound CN1CC(N)CN1CC1=CC=CC=C1 NNRDMDHLPHFDSE-UHFFFAOYSA-N 0.000 description 1
- XEFCZINKJMACOI-UHFFFAOYSA-N 1-benzyl-2-methylpyrazolidin-4-ol Chemical compound CN1CC(O)CN1CC1=CC=CC=C1 XEFCZINKJMACOI-UHFFFAOYSA-N 0.000 description 1
- NSHLYLMEOSXOCW-UHFFFAOYSA-N 1-methyl-2-propan-2-ylpyrazolidin-4-amine Chemical compound CC(C)N1CC(N)CN1C NSHLYLMEOSXOCW-UHFFFAOYSA-N 0.000 description 1
- NHHNBWPTEMBVLN-UHFFFAOYSA-N 2-propan-2-yloxypropane;2,2,4-trimethylpentane Chemical compound CC(C)OC(C)C.CC(C)CC(C)(C)C NHHNBWPTEMBVLN-UHFFFAOYSA-N 0.000 description 1
- BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-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
- QNOOQQCTAPGUOV-UHFFFAOYSA-N 4-chloro-1,2-dimethylpyrazolidine Chemical compound CN1CC(Cl)CN1C QNOOQQCTAPGUOV-UHFFFAOYSA-N 0.000 description 1
- 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 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- XBTRXGPECITWFW-UHFFFAOYSA-L NC(=O)N.S(=O)(=O)([O-])[O-].[Na+].[Na+] Chemical compound NC(=O)N.S(=O)(=O)([O-])[O-].[Na+].[Na+] XBTRXGPECITWFW-UHFFFAOYSA-L 0.000 description 1
- XDDYPYOLQHVLEG-UHFFFAOYSA-N NC1CN(N(C1)C(C)C)C.NC1CN(N(C1)C(C)C)C Chemical compound NC1CN(N(C1)C(C)C)C.NC1CN(N(C1)C(C)C)C XDDYPYOLQHVLEG-UHFFFAOYSA-N 0.000 description 1
- RIMJZGWRVAICLL-UHFFFAOYSA-N NC1CN(N(C1)C1CCCCC1)C.C(C=CC(=O)O)(=O)O.NC1CN(N(C1)C1CCCCC1)C Chemical compound NC1CN(N(C1)C1CCCCC1)C.C(C=CC(=O)O)(=O)O.NC1CN(N(C1)C1CCCCC1)C RIMJZGWRVAICLL-UHFFFAOYSA-N 0.000 description 1
- RRXRGULGMMPBEY-UHFFFAOYSA-N NC1CN(N(C1)CC1=CC=CC=C1)C.NC1CN(N(C1)CC1=CC=CC=C1)C Chemical compound NC1CN(N(C1)CC1=CC=CC=C1)C.NC1CN(N(C1)CC1=CC=CC=C1)C RRXRGULGMMPBEY-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- LLMUIHMJPJEPGX-UHFFFAOYSA-N [N]NC(=O)C1=CC=CC=C1 Chemical group [N]NC(=O)C1=CC=CC=C1 LLMUIHMJPJEPGX-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- UDSRUCAJZSIRHZ-UHFFFAOYSA-N benzamide dihydrochloride Chemical compound Cl.Cl.NC(=O)C1=CC=CC=C1.NC(=O)C1=CC=CC=C1 UDSRUCAJZSIRHZ-UHFFFAOYSA-N 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical class C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 235000021152 breakfast Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 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
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 230000000779 depleting effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 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
- 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
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 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 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- MWKPHEKRHBZGIV-UHFFFAOYSA-N pyrazolidin-4-amine Chemical class NC1CNNC1 MWKPHEKRHBZGIV-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 235000021195 test diet Nutrition 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
- 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI832671A FI70706C (fi) | 1977-08-19 | 1983-07-22 | 4-aminopyrazolidinderivat till anvaendning som mellanprodukt vid framstaellning av n-(4-pyrazolidinyl)bensamider |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82603177A | 1977-08-19 | 1977-08-19 | |
| US82603177 | 1977-08-19 | ||
| US90036978A | 1978-04-26 | 1978-04-26 | |
| US90036978 | 1978-04-26 | ||
| US93012578A | 1978-08-01 | 1978-08-01 | |
| US93012578 | 1978-08-01 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI782507A7 FI782507A7 (fi) | 1979-02-20 |
| FI68044B FI68044B (fi) | 1985-03-29 |
| FI68044C true FI68044C (fi) | 1985-07-10 |
Family
ID=27420183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI782507A FI68044C (fi) | 1977-08-19 | 1978-08-16 | Foerfarande foer framstaellning av terapeutiskt aktiva n-(4-pyrazolidinyl)bensamider |
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
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4284629A (en) | Process for the preparation of 4-pyridone-3-carboxylic acids and/or derivatives thereof | |
| DE69232003T2 (de) | Benzanilidderivate als 5-HT1D-Antagonisten | |
| US5219859A (en) | Indole derivatives, preparation processes and medicinal products containing them | |
| AU638096B2 (en) | Novel benzimidazole and azabenzimidazole derivatives which are thromboxane receptor antagonists, their methods of preparation, synthesis intermediates and pharmaceutical compositions in which they are present | |
| US4093734A (en) | Amino-benzoic acid amides | |
| US5073671A (en) | 1-(benzyl or pyridylmethyl)-4 or 5-aminomethyl-pyrrolidin-2-ones | |
| HU185857B (en) | Process for preparing imidazol/1,2-a/pyridines | |
| HU184966B (en) | Process for producing phenyl-piperazine derivatives of anti-agression activity | |
| AT391694B (de) | Verfahren zur herstellung von neuen ethylendiaminmonoamid-derivaten | |
| US4207327A (en) | N-(4-Pyrazolidinyl)benzamides and their amino precursors | |
| NO832016L (no) | Fremgangsmaate for fremstilling av terapeutisk aktive pyrazinon-derivater | |
| FI105029B (fi) | Menetelmä terapeuttisesti käyttökelpoisten 4-amino-2-ureido-pyrimidiini-5-karboksyylihappoamidien valmistamiseksi, välituotteita ja niiden valmistus | |
| FI68044C (fi) | Foerfarande foer framstaellning av terapeutiskt aktiva n-(4-pyrazolidinyl)bensamider | |
| CS274446B2 (en) | Method of 1-acyl-3-/4-/2-pyrimidinyl/-1-piperazinyl/propanes production | |
| HU180429B (en) | Process for producing 2-bromo-6-fluoro-n-2-imidasolidinilidine-benzamine and acid addi ional salts of antihypertensive activity | |
| JPH05117273A (ja) | 医薬化合物 | |
| US5523310A (en) | 1,2,3-triazole derivatives | |
| US3597429A (en) | Derivatives of tetrazolyl alkanoic acids | |
| JPH01203379A (ja) | さらに水素化された１―ベンゾオキサシクロアルキルピリジンカルボン酸類 | |
| US3715364A (en) | Nitroimidazole carboxamides | |
| HU193556B (en) | Process for preparing benzamide derivatives | |
| FI70706B (fi) | 4-aminopyrazolidinderivat till anvaendning som mellanprodukt vid framstaellning av n-(4-pyrazolidinyl)bensamider | |
| GB2043060A (en) | 4-substituted 2-iminoimidazolidine compounds | |
| US5352692A (en) | Thiophene-2-carboxylic acid derivatives | |
| USRE32975E (en) | 4-Pyridone-3-carboxylic acids and/or derivatives thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB | Publication of examined application | ||
| BB | Publication of examined application | ||
| MM | Patent lapsed |
Owner name: A.H. ROBINS COMPANY, INCORPORATED |