CA1109880A - N-(4-pyrazolidinyl) benzamides - Google Patents

N-(4-pyrazolidinyl) benzamides

Info

Publication number: CA1109880A
Authority: CA; Canada
Prior art keywords: amino; process according; compound; methylpyrazolidine; prepared
Prior art date: 1977-08-19
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA362,371A

Other languages

English (en)

Inventor

Carl D. Lunsford

Albert D. Cale, Jr.

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

AH Robins Co Inc

Original Assignee

AH Robins Co Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-08-19

Filing date

1980-10-14

Publication date

1981-09-29

1978-08-18 Priority claimed from CA309,651A external-priority patent/CA1105037A/fr

1980-10-14 Application filed by AH Robins Co Inc filed Critical AH Robins Co Inc

1980-10-14 Priority to CA362,371A priority Critical patent/CA1109880A/fr

1981-09-29 Application granted granted Critical

1981-09-29 Publication of CA1109880A publication Critical patent/CA1109880A/fr

Status Expired legal-status Critical Current

Links

BBDOMHXDXUDXPB-UHFFFAOYSA-N n-pyrazolidin-4-ylbenzamide Chemical class C=1C=CC=CC=1C(=O)NC1CNNC1 BBDOMHXDXUDXPB-UHFFFAOYSA-N 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 25
125000000217 alkyl group Chemical group 0.000 claims abstract description 24
239000001257 hydrogen Substances 0.000 claims abstract description 13
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
MWKPHEKRHBZGIV-UHFFFAOYSA-N pyrazolidin-4-amine Chemical class NC1CNNC1 MWKPHEKRHBZGIV-UHFFFAOYSA-N 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 28
-1 4-chloro-1-benzyl-2-methylpyrazolidine Chemical compound 0.000 claims description 14
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 13
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
239000000908 ammonium hydroxide Substances 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
238000010438 heat treatment Methods 0.000 claims description 6
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
NNRDMDHLPHFDSE-UHFFFAOYSA-N 1-benzyl-2-methylpyrazolidin-4-amine Chemical compound CN1CC(N)CN1CC1=CC=CC=C1 NNRDMDHLPHFDSE-UHFFFAOYSA-N 0.000 claims description 4
NSHLYLMEOSXOCW-UHFFFAOYSA-N 1-methyl-2-propan-2-ylpyrazolidin-4-amine Chemical compound CC(C)N1CC(N)CN1C NSHLYLMEOSXOCW-UHFFFAOYSA-N 0.000 claims description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
FQWUIOJVBDSHQH-UHFFFAOYSA-N 1,2-diethylpyrazolidin-4-amine Chemical compound CCN1CC(N)CN1CC FQWUIOJVBDSHQH-UHFFFAOYSA-N 0.000 claims description 3
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 claims description 3
XYUOOPRAZMJZIY-UHFFFAOYSA-N 1-cyclohexyl-2-methylpyrazolidin-4-amine Chemical compound CN1CC(N)CN1C1CCCCC1 XYUOOPRAZMJZIY-UHFFFAOYSA-N 0.000 claims description 3
150000003973 alkyl amines Chemical class 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
FBKMPHZLJCLLSG-UHFFFAOYSA-N 4-chloro-1,2-diethylpyrazolidine Chemical compound CCN1CC(Cl)CN1CC FBKMPHZLJCLLSG-UHFFFAOYSA-N 0.000 claims description 2
QNOOQQCTAPGUOV-UHFFFAOYSA-N 4-chloro-1,2-dimethylpyrazolidine Chemical compound CN1CC(Cl)CN1C QNOOQQCTAPGUOV-UHFFFAOYSA-N 0.000 claims description 2
229910021529 ammonia Inorganic materials 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 7
239000000126 substance Substances 0.000 claims 7
229940043379 ammonium hydroxide Drugs 0.000 claims 4
235000011114 ammonium hydroxide Nutrition 0.000 claims 4
ZAOBFIURDGPCBP-UHFFFAOYSA-N 1,2-dimethylpyrazolidin-4-amine Chemical compound CN1CC(N)CN1C ZAOBFIURDGPCBP-UHFFFAOYSA-N 0.000 claims 2
HMQFUSFGZAPMEH-UHFFFAOYSA-N 1,2-dimethylpyrazolidin-4-ol Chemical compound CN1CC(O)CN1C HMQFUSFGZAPMEH-UHFFFAOYSA-N 0.000 claims 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
239000001530 fumaric acid Substances 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
OAHKWDDSKCRNFE-UHFFFAOYSA-N phenylmethanesulfonyl chloride Chemical compound ClS(=O)(=O)CC1=CC=CC=C1 OAHKWDDSKCRNFE-UHFFFAOYSA-N 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 12
230000030136 gastric emptying Effects 0.000 abstract description 7
230000003474 anti-emetic effect Effects 0.000 abstract description 6
239000002111 antiemetic agent Substances 0.000 abstract description 4
239000000543 intermediate Substances 0.000 abstract description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 58
239000000243 solution Substances 0.000 description 33
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
229960001701 chloroform Drugs 0.000 description 29
239000000203 mixture Substances 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
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 12
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 11
229910052938 sodium sulfate Inorganic materials 0.000 description 11
235000011152 sodium sulphate Nutrition 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000000047 product Substances 0.000 description 10
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
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
210000002784 stomach Anatomy 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
239000000463 material 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
235000012054 meals Nutrition 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
206010047700 Vomiting Diseases 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
125000004432 carbon atom Chemical group C* 0.000 description 4
238000001816 cooling Methods 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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 3
241000220479 Acacia Species 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 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
229910000831 Steel Inorganic materials 0.000 description 3
229940054066 benzamide antipsychotics Drugs 0.000 description 3
150000003936 benzamides Chemical class 0.000 description 3
239000003814 drug Substances 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
125000001153 fluoro group Chemical group F* 0.000 description 3
235000011167 hydrochloric acid Nutrition 0.000 description 3
229960000443 hydrochloric acid Drugs 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 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
229910000027 potassium carbonate Inorganic materials 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000010959 steel Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
UXILCSZJNQSVKU-UHFFFAOYSA-N 1,2-diethylpyrazolidin-4-ol Chemical compound CCN1CC(O)CN1CC UXILCSZJNQSVKU-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
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
NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000003929 acidic solution Substances 0.000 description 2
239000013543 active substance Substances 0.000 description 2
239000002585 base Substances 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
235000010233 benzoic acid Nutrition 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000002026 chloroform extract Substances 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
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
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
150000002431 hydrogen Chemical group 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 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
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 2
239000012074 organic phase Substances 0.000 description 2
125000003072 pyrazolidinyl group Chemical group 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
239000002904 solvent Substances 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
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
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 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
XEFCZINKJMACOI-UHFFFAOYSA-N 1-benzyl-2-methylpyrazolidin-4-ol Chemical compound CN1CC(O)CN1CC1=CC=CC=C1 XEFCZINKJMACOI-UHFFFAOYSA-N 0.000 description 1
COPYTBVUDGSNSX-UHFFFAOYSA-N 1-cyclohexyl-2-methylpyrazolidine Chemical compound C1(CCCCC1)N1N(CCC1)C COPYTBVUDGSNSX-UHFFFAOYSA-N 0.000 description 1
FYOTVMFIGGPSKD-UHFFFAOYSA-N 1-hydroxypyrazolidin-4-amine Chemical class NC1CNN(O)C1 FYOTVMFIGGPSKD-UHFFFAOYSA-N 0.000 description 1
NFHQYWPOTLXIQP-UHFFFAOYSA-N 1-methylpyrazolidine Chemical compound CN1CCCN1 NFHQYWPOTLXIQP-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
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 1
BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-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
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
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
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 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
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
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
OTQBAPAIMZWLGQ-UHFFFAOYSA-N 4-amino-5-chloro-n-(1-cyclohexyl-2-methylpyrazolidin-4-yl)-2-methoxybenzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NC1CN(C2CCCCC2)N(C)C1 OTQBAPAIMZWLGQ-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
RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
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241000282326 Felis catus Species 0.000 description 1
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241000282414 Homo sapiens Species 0.000 description 1
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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
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125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
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239000000010 aprotic solvent Substances 0.000 description 1
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230000037396 body weight Effects 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
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
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239000003795 chemical substances by application Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000002178 crystalline material Substances 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
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
230000000994 depressogenic effect Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000012065 filter cake 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
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
150000002367 halogens Chemical group 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
150000002500 ions Chemical class 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
239000008101 lactose Substances 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
150000002688 maleic acid derivatives Chemical class 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 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
IARBYTDFQKRYFM-UHFFFAOYSA-N n-(1,2-dimethylpyrazolidin-4-yl)-2-methoxy-5-sulfamoylbenzamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(=O)NC1CN(C)N(C)C1 IARBYTDFQKRYFM-UHFFFAOYSA-N 0.000 description 1
OGMIGGKUOGNUIV-UHFFFAOYSA-N n-(1,2-dimethylpyrazolidin-4-yl)-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1CN(C)N(C)C1 OGMIGGKUOGNUIV-UHFFFAOYSA-N 0.000 description 1
HJHIKEWWBRKQAR-UHFFFAOYSA-N n-(1,2-dimethylpyrazolidin-4-yl)-4-methylbenzamide Chemical compound C1N(C)N(C)CC1NC(=O)C1=CC=C(C)C=C1 HJHIKEWWBRKQAR-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
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
235000005985 organic acids Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000006201 parenteral dosage form Substances 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
FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000013223 sprague-dawley female rat Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form 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
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

Landscapes

Plural Heterocyclic Compounds (AREA)

CA362,371A 1977-08-19 1980-10-14 N-(4-pyrazolidinyl) benzamides Expired CA1109880A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA362,371A CA1109880A (fr)	1977-08-19	1980-10-14	N-(4-pyrazolidinyl) benzamides

Applications Claiming Priority (8)

Application Number	Priority Date	Filing Date	Title
US82603177A	1977-08-19	1977-08-19
US826,031		1977-08-19
US90036978A	1978-04-26	1978-04-26
US900,369		1978-04-26
US93012578A	1978-08-01	1978-08-01
CA309,651A CA1105037A (fr)	1977-08-19	1978-08-18	Traduction non-disponible
CA362,371A CA1109880A (fr)	1977-08-19	1980-10-14	N-(4-pyrazolidinyl) benzamides
US930,125		1992-08-14

Publications (1)

Publication Number	Publication Date
CA1109880A true CA1109880A (fr)	1981-09-29

Family

ID=27508123

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA362,371A Expired CA1109880A (fr)	1977-08-19	1980-10-14	N-(4-pyrazolidinyl) benzamides

Country Status (1)

Country	Link
CA (1)	CA1109880A (fr)

1980
- 1980-10-14 CA CA362,371A patent/CA1109880A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-09-29	MKEX	Expiry

Publication	Publication Date	Title
DE69232003T2 (de)	2002-04-25	Benzanilidderivate als 5-HT1D-Antagonisten
US4207327A (en)	1980-06-10	N-(4-Pyrazolidinyl)benzamides and their amino precursors
DE3700408A1 (de)	1987-07-09	Indolderivate, sie enthaltende pharmazeutische zubereitungen und verfahren zu ihrer herstellung
JPS6212788B2 (fr)	1987-03-20
CA1171086A (fr)	1984-07-17	Phenyl-2-(pyridyloxy)-2-ethylamines et composes isosteres; preparation et applications
JPS59141558A (ja)	1984-08-14	２−イミノ−ピロリジン類，その製造法および治療用組成物
US3840598A (en)	1974-10-08	4,4'-disubstituted-bis(benzamides)
CA1109880A (fr)	1981-09-29	N-(4-pyrazolidinyl) benzamides
CA1077953A (fr)	1980-05-20	Methode pour la production de nouveaux composes chimiques
EP0279633B1 (fr)	1993-04-07	Agents anticonvulsifs
HU198454B (en)	1989-10-30	Process for production of new derivatives of tetrahydrospiridin and medical compositions containing these compounds
SE431869B (sv)	1984-03-05	Forfarande for framstellning av n-(1-cyklohexyl-3-pyrrolidinyl)-bensamider med antiemetisk verkan
JPS61215361A (ja)	1986-09-25	抗痙攣剤
CA1105037A (fr)	1981-07-14	Traduction non-disponible
AT390948B (de)	1990-07-25	Verfahren zur herstellung von neuen benzamid-derivaten
CA1094070A (fr)	1981-01-20	Traduction non-disponible
US4163789A (en)	1979-08-07	Anti-psychotic (cycloalkenylalkylpiperidino) benzamides
US4161532A (en)	1979-07-17	N-(1'-ethyl-2'-oxo-5'-pyrrolidinylmethyl) benzamide compounds and derivatives, method of preparation and pharmaceutical preparations
CA2012313C (fr)	1998-10-06	Derives de l'acide thienylacetique, procede pour leur preparation, leur utilisation, produits pharmaceutiques contenant ceux-ci et leur preparation
US3597429A (en)	1971-08-03	Derivatives of tetrazolyl alkanoic acids
JPS6015616B2 (ja)	1985-04-20	Ｎ−２−（ピロリジニルメチル）置換ベンズアミド誘導体またはその塩類の製造法
US4143150A (en)	1979-03-06	Derivatives of oxanilic acid
US4153702A (en)	1979-05-08	Basically alkylated dithiosalicyclic acid amides and their use as medicaments
US3121723A (en)	1964-02-18	Lower alkyl n-(tertiary-amino-lower-alkyl) lower alkamates and quaternary ammonium salts thereof
AT366371B (de)	1982-04-13	Verfahren zur herstellung von neuen n-(4pyrazolidinyl)benzamiden, deren salzen und optischaktiven formen