CH626067A5 - Process for the preparation of 1-(lower aminoalkyl)-3,4-diphenyl-1H-pyrazoles - Google Patents
Process for the preparation of 1-(lower aminoalkyl)-3,4-diphenyl-1H-pyrazoles Download PDFInfo
- Publication number
- CH626067A5 CH626067A5 CH1568677A CH1568677A CH626067A5 CH 626067 A5 CH626067 A5 CH 626067A5 CH 1568677 A CH1568677 A CH 1568677A CH 1568677 A CH1568677 A CH 1568677A CH 626067 A5 CH626067 A5 CH 626067A5
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- diphenyl
- group
- compounds
- dimethylamino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 11
- 239000002253 acid Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 11
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 8
- 239000000935 antidepressant agent Substances 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- -1 amino, methylamino, dimethylamino Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000000730 antalgic agent Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 4
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 2
- 239000007868 Raney catalyst Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- MQWYZELNDPRANJ-UHFFFAOYSA-N 4,5-diphenyl-1h-pyrazole Chemical compound C1=NNC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 MQWYZELNDPRANJ-UHFFFAOYSA-N 0.000 description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
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- 239000000126 substance Substances 0.000 description 5
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- 241000699670 Mus sp. Species 0.000 description 4
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- 239000000725 suspension Substances 0.000 description 4
- 238000002211 ultraviolet spectrum Methods 0.000 description 4
- PUXUEPFDKXBXMV-UHFFFAOYSA-N 3-(3,4-diphenylpyrazol-1-yl)propanenitrile Chemical compound N=1N(CCC#N)C=C(C=2C=CC=CC=2)C=1C1=CC=CC=C1 PUXUEPFDKXBXMV-UHFFFAOYSA-N 0.000 description 3
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- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 2
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- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
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- 238000010998 test method Methods 0.000 description 2
- 229960005333 tetrabenazine Drugs 0.000 description 2
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
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- VBSTXRUAXCTZBQ-UHFFFAOYSA-N 1-hexyl-4-phenylpiperazine Chemical compound C1CN(CCCCCC)CCN1C1=CC=CC=C1 VBSTXRUAXCTZBQ-UHFFFAOYSA-N 0.000 description 1
- WVUCESKLWMCJOE-UHFFFAOYSA-N 2-(3,4-diphenylpyrazol-1-yl)-n,n-diethylethanamine;hydrochloride Chemical group Cl.N=1N(CCN(CC)CC)C=C(C=2C=CC=CC=2)C=1C1=CC=CC=C1 WVUCESKLWMCJOE-UHFFFAOYSA-N 0.000 description 1
- HJLBUFXLUGRAIN-UHFFFAOYSA-N 2-(3,5-diphenylpyrazol-1-yl)-n,n-diethylethanamine Chemical compound CCN(CC)CCN1N=C(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 HJLBUFXLUGRAIN-UHFFFAOYSA-N 0.000 description 1
- YOBCADXVWSICRP-UHFFFAOYSA-N 2-(3,5-diphenylpyrazol-1-yl)ethanamine Chemical compound NCCN1N=C(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 YOBCADXVWSICRP-UHFFFAOYSA-N 0.000 description 1
- XGJZYXZSZKPQKF-UHFFFAOYSA-N 2-(3-phenylpyrazol-1-yl)ethanamine Chemical class NCCN1C=CC(C=2C=CC=CC=2)=N1 XGJZYXZSZKPQKF-UHFFFAOYSA-N 0.000 description 1
- VYWYYJYRVSBHJQ-UHFFFAOYSA-N 3,5-dinitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 VYWYYJYRVSBHJQ-UHFFFAOYSA-N 0.000 description 1
- JXHKUYQCEJILEI-UHFFFAOYSA-N 3,5-diphenyl-1h-pyrazole Chemical compound C=1C(C=2C=CC=CC=2)=NNC=1C1=CC=CC=C1 JXHKUYQCEJILEI-UHFFFAOYSA-N 0.000 description 1
- DYBIAQJVTNNTBC-UHFFFAOYSA-N 3-(3,4-diphenylpyrazol-1-yl)-n,n-diethylpropan-1-amine;hydrochloride Chemical compound Cl.N=1N(CCCN(CC)CC)C=C(C=2C=CC=CC=2)C=1C1=CC=CC=C1 DYBIAQJVTNNTBC-UHFFFAOYSA-N 0.000 description 1
- LSLIDHDYMCWJRJ-UHFFFAOYSA-N 3-(3,4-diphenylpyrazol-1-yl)-n,n-dimethylpropan-1-amine;dihydrochloride Chemical compound Cl.Cl.N=1N(CCCN(C)C)C=C(C=2C=CC=CC=2)C=1C1=CC=CC=C1 LSLIDHDYMCWJRJ-UHFFFAOYSA-N 0.000 description 1
- BXZHZQAPZWGQAH-UHFFFAOYSA-N 3-(3,4-diphenylpyrazol-1-yl)-n-methylpropan-1-amine;hydrochloride Chemical compound Cl.N=1N(CCCNC)C=C(C=2C=CC=CC=2)C=1C1=CC=CC=C1 BXZHZQAPZWGQAH-UHFFFAOYSA-N 0.000 description 1
- YEEUAVDZLNTQJK-UHFFFAOYSA-N 3-(3,5-diphenylpyrazol-1-yl)propan-1-amine Chemical compound NCCCN1N=C(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 YEEUAVDZLNTQJK-UHFFFAOYSA-N 0.000 description 1
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- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- UPDHOTIATMFGCI-UHFFFAOYSA-N butylarsonic acid Chemical compound CCCC[As](O)(O)=O UPDHOTIATMFGCI-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 1
- 235000019416 cholic acid Nutrition 0.000 description 1
- 229960002471 cholic acid Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001427 coherent effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- LRBQNJMCXXYXIU-QWKBTXIPSA-N gallotannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@H]2[C@@H]([C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-QWKBTXIPSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000002788 histamine agent Substances 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229940045996 isethionic acid Drugs 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- GCCQLYLPTCJCCN-UHFFFAOYSA-N n,n-dimethyl-2-(4-methyl-3-phenylpyrazol-1-yl)ethanamine Chemical compound CN(C)CCN1C=C(C)C(C=2C=CC=CC=2)=N1 GCCQLYLPTCJCCN-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 239000000196 tragacanth Substances 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
- 230000009466 transformation Effects 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
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75231676A | 1976-12-20 | 1976-12-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH626067A5 true CH626067A5 (en) | 1981-10-30 |
Family
ID=25025781
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1568677A CH626067A5 (en) | 1976-12-20 | 1977-12-20 | Process for the preparation of 1-(lower aminoalkyl)-3,4-diphenyl-1H-pyrazoles |
| CH237981A CH627170A5 (en) | 1976-12-20 | 1981-04-08 | Process for the preparation of 1-(lower aminoalkyl)-3,4-diphenyl-1H-pyrazoles |
| CH237881A CH627451A5 (en) | 1976-12-20 | 1981-04-08 | Process for the preparation of 1-(lower aminoalkyl)-3,4-diphenyl-1H-pyrazoles |
| CH238081A CH627171A5 (en) | 1976-12-20 | 1981-04-08 | Process for the preparation of 1-(lower aminoalkyl)-3,4-diphenyl-1H-pyrazoles |
| CH254481A CH627172A5 (en) | 1976-12-20 | 1981-04-16 | Process for the preparation of 1-(lower aminoalkyl)-3,4-diphenyl-1H-pyrazoles |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH237981A CH627170A5 (en) | 1976-12-20 | 1981-04-08 | Process for the preparation of 1-(lower aminoalkyl)-3,4-diphenyl-1H-pyrazoles |
| CH237881A CH627451A5 (en) | 1976-12-20 | 1981-04-08 | Process for the preparation of 1-(lower aminoalkyl)-3,4-diphenyl-1H-pyrazoles |
| CH238081A CH627171A5 (en) | 1976-12-20 | 1981-04-08 | Process for the preparation of 1-(lower aminoalkyl)-3,4-diphenyl-1H-pyrazoles |
| CH254481A CH627172A5 (en) | 1976-12-20 | 1981-04-16 | Process for the preparation of 1-(lower aminoalkyl)-3,4-diphenyl-1H-pyrazoles |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS5377059A (fi) |
| AR (1) | AR214655A1 (fi) |
| AT (2) | AT363071B (fi) |
| AU (1) | AU511482B2 (fi) |
| BE (1) | BE862038A (fi) |
| CA (1) | CA1098527A (fi) |
| CH (5) | CH626067A5 (fi) |
| DE (1) | DE2756852A1 (fi) |
| DK (1) | DK146624C (fi) |
| ES (6) | ES465206A1 (fi) |
| FI (1) | FI66353C (fi) |
| FR (1) | FR2421887A1 (fi) |
| GB (1) | GB1565319A (fi) |
| HK (1) | HK36785A (fi) |
| IE (1) | IE46612B1 (fi) |
| IL (1) | IL53498A (fi) |
| LU (1) | LU78723A1 (fi) |
| MX (1) | MX4722E (fi) |
| NL (2) | NL7713811A (fi) |
| NO (1) | NO147108C (fi) |
| NZ (1) | NZ185811A (fi) |
| PH (1) | PH15728A (fi) |
| PT (1) | PT67431B (fi) |
| SE (1) | SE443560B (fi) |
| ZA (1) | ZA777163B (fi) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4965825A (en) | 1981-11-03 | 1990-10-23 | The Personalized Mass Media Corporation | Signal processing apparatus and methods |
| USRE47642E1 (en) | 1981-11-03 | 2019-10-08 | Personalized Media Communications LLC | Signal processing apparatus and methods |
| US7831204B1 (en) | 1981-11-03 | 2010-11-09 | Personalized Media Communications, Llc | Signal processing apparatus and methods |
| US4994482A (en) * | 1989-07-31 | 1991-02-19 | Bristol-Myers Squibb Company | Arylpyrazol derivatives as anti-platelet agents, compositions and use |
| FR2786188B1 (fr) * | 1998-11-24 | 2002-10-31 | Hoechst Marion Roussel Inc | Nouveaux derives de l'erythromycine, leur procede de preparation et leur applicaion comme medicaments |
-
1977
- 1977-11-28 CA CA291,869A patent/CA1098527A/en not_active Expired
- 1977-11-29 IE IE2418/77A patent/IE46612B1/en unknown
- 1977-11-29 NZ NZ185811A patent/NZ185811A/xx unknown
- 1977-11-30 IL IL53498A patent/IL53498A/xx unknown
- 1977-12-01 GB GB50129/77A patent/GB1565319A/en not_active Expired
- 1977-12-02 ZA ZA00777163A patent/ZA777163B/xx unknown
- 1977-12-06 AU AU31262/77A patent/AU511482B2/en not_active Expired
- 1977-12-08 MX MX776675U patent/MX4722E/es unknown
- 1977-12-09 PH PH20537A patent/PH15728A/en unknown
- 1977-12-13 NL NL7713811A patent/NL7713811A/xx not_active Application Discontinuation
- 1977-12-16 NO NO774338A patent/NO147108C/no unknown
- 1977-12-16 FR FR7738112A patent/FR2421887A1/fr active Granted
- 1977-12-16 AT AT0902077A patent/AT363071B/de active
- 1977-12-19 SE SE7714461A patent/SE443560B/sv not_active IP Right Cessation
- 1977-12-19 PT PT67431A patent/PT67431B/pt unknown
- 1977-12-19 DK DK566277A patent/DK146624C/da not_active IP Right Cessation
- 1977-12-19 ES ES465206A patent/ES465206A1/es not_active Expired
- 1977-12-19 FI FI773836A patent/FI66353C/fi not_active IP Right Cessation
- 1977-12-20 JP JP15349777A patent/JPS5377059A/ja active Granted
- 1977-12-20 BE BE1008592A patent/BE862038A/xx not_active IP Right Cessation
- 1977-12-20 CH CH1568677A patent/CH626067A5/fr not_active IP Right Cessation
- 1977-12-20 DE DE19772756852 patent/DE2756852A1/de active Granted
- 1977-12-20 LU LU78723A patent/LU78723A1/xx unknown
- 1977-12-20 AR AR270427A patent/AR214655A1/es active
-
1978
- 1978-09-14 ES ES473376A patent/ES473376A1/es not_active Expired
- 1978-09-14 ES ES473366A patent/ES473366A1/es not_active Expired
- 1978-09-14 ES ES473365A patent/ES473365A1/es not_active Expired
- 1978-09-14 ES ES473364A patent/ES473364A1/es not_active Expired
- 1978-09-14 ES ES473367A patent/ES473367A1/es not_active Expired
-
1980
- 1980-06-06 AT AT0299780A patent/AT363074B/de not_active IP Right Cessation
-
1981
- 1981-04-08 CH CH237981A patent/CH627170A5/fr not_active IP Right Cessation
- 1981-04-08 CH CH237881A patent/CH627451A5/fr not_active IP Right Cessation
- 1981-04-08 CH CH238081A patent/CH627171A5/fr not_active IP Right Cessation
- 1981-04-16 CH CH254481A patent/CH627172A5/fr not_active IP Right Cessation
-
1985
- 1985-05-09 HK HK367/85A patent/HK36785A/xx unknown
-
1990
- 1990-10-09 NL NL9002188A patent/NL9002188A/nl not_active Application Discontinuation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |