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 PDF

Info

Publication number: CH626067A5
Authority: CH; Switzerland
Prior art keywords: acid; diphenyl; group; compounds; dimethylamino
Prior art date: 1976-12-20

Application number

CH1568677A

Other languages

English (en)

French (fr)

Inventor

Denis Mahlon Bailey

Original Assignee

Sterling Drug 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.)

1976-12-20

Filing date

1977-12-20

Publication date

1981-10-30

1977-12-20 Application filed by Sterling Drug Inc filed Critical Sterling Drug Inc

1981-10-30 Publication of CH626067A5 publication Critical patent/CH626067A5/fr

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
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
230000000202 analgesic effect Effects 0.000 description 4
229940005513 antidepressants Drugs 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000004817 gas chromatography Methods 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
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
206010010904 Convulsion Diseases 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
229960004373 acetylcholine Drugs 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
230000029936 alkylation Effects 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
230000001430 anti-depressive effect Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
230000036461 convulsion Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
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
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-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
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
230000003187 abdominal effect Effects 0.000 description 2
229940035676 analgesics Drugs 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
238000010586 diagram Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
239000004310 lactic acid Substances 0.000 description 2
235000014655 lactic acid Nutrition 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
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
239000003960 organic solvent Substances 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
238000010998 test method Methods 0.000 description 2
229960005333 tetrabenazine Drugs 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
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
BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 1
AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
NAOLWIGVYRIGTP-UHFFFAOYSA-N 1,3,5-trihydroxyanthracene-9,10-dione Chemical compound C1=CC(O)=C2C(=O)C3=CC(O)=CC(O)=C3C(=O)C2=C1 NAOLWIGVYRIGTP-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
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
ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004380 Cholic acid Substances 0.000 description 1
AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 1
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
239000001263 FEMA 3042 Substances 0.000 description 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products 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-PPKXGCFTSA-N 0.000 description 1
SIOXPEMLGUPBBT-UHFFFAOYSA-N Picolinic acid Natural products OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
241000906446 Theraps Species 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
JACRWUWPXAESPB-QMMMGPOBSA-N Tropic acid Natural products OC[C@H](C(O)=O)C1=CC=CC=C1 JACRWUWPXAESPB-QMMMGPOBSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
229940000488 arsenic acid Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
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)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH1568677A 1976-12-20 1977-12-20 Process for the preparation of 1-(lower aminoalkyl)-3,4-diphenyl-1H-pyrazoles CH626067A5 (en)

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
CH238081A CH627171A5 (en)	1976-12-20	1981-04-08	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
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
CH238081A CH627171A5 (en)	1976-12-20	1981-04-08	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
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 (de)
AR (1)	AR214655A1 (de)
AT (2)	AT363071B (de)
AU (1)	AU511482B2 (de)
BE (1)	BE862038A (de)
CA (1)	CA1098527A (de)
CH (5)	CH626067A5 (de)
DE (1)	DE2756852A1 (de)
DK (1)	DK146624C (de)
ES (6)	ES465206A1 (de)
FI (1)	FI66353C (de)
FR (1)	FR2421887A1 (de)
GB (1)	GB1565319A (de)
HK (1)	HK36785A (de)
IE (1)	IE46612B1 (de)
IL (1)	IL53498A (de)
LU (1)	LU78723A1 (de)
MX (1)	MX4722E (de)
NL (2)	NL7713811A (de)
NO (1)	NO147108C (de)
NZ (1)	NZ185811A (de)
PH (1)	PH15728A (de)
PT (1)	PT67431B (de)
SE (1)	SE443560B (de)
ZA (1)	ZA777163B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
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
US7831204B1 (en)	1981-11-03	2010-11-09	Personalized Media Communications, Llc	Signal processing apparatus and methods
USRE47642E1 (en)	1981-11-03	2019-10-08	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 AT AT0902077A patent/AT363071B/de active
- 1977-12-16 NO NO774338A patent/NO147108C/no unknown
- 1977-12-16 FR FR7738112A patent/FR2421887A1/fr active Granted
- 1977-12-19 FI FI773836A patent/FI66353C/fi not_active IP Right Cessation
- 1977-12-19 PT PT67431A patent/PT67431B/pt unknown
- 1977-12-19 SE SE7714461A patent/SE443560B/sv not_active IP Right Cessation
- 1977-12-19 DK DK566277A patent/DK146624C/da not_active IP Right Cessation
- 1977-12-19 ES ES465206A patent/ES465206A1/es not_active Expired
- 1977-12-20 BE BE1008592A patent/BE862038A/xx not_active IP Right Cessation
- 1977-12-20 JP JP15349777A patent/JPS5377059A/ja active Granted
- 1977-12-20 CH CH1568677A patent/CH626067A5/fr not_active IP Right Cessation
- 1977-12-20 LU LU78723A patent/LU78723A1/xx unknown
- 1977-12-20 DE DE19772756852 patent/DE2756852A1/de active Granted
- 1977-12-20 AR AR270427A patent/AR214655A1/es active
1978
- 1978-09-14 ES ES473364A patent/ES473364A1/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 ES473367A patent/ES473367A1/es not_active Expired
- 1978-09-14 ES ES473376A patent/ES473376A1/es not_active Expired
1980
- 1980-06-06 AT AT0299780A patent/AT363074B/de not_active IP Right Cessation
1981
- 1981-04-08 CH CH238081A patent/CH627171A5/fr not_active IP Right Cessation
- 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
- 1981-04-16 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

Also Published As

Publication number	Publication date
FR2421887B1 (de)	1982-03-12
NL7713811A (nl)	1978-06-22
NO147108C (no)	1983-02-02
IL53498A (en)	1981-11-30
GB1565319A (en)	1980-04-16
CH627172A5 (en)	1981-12-31
IE46612B1 (en)	1983-08-10
NO774338L (no)	1978-06-21
DK146624B (da)	1983-11-21
DE2756852C2 (de)	1988-11-10
AU3126277A (en)	1979-06-14
ZA777163B (en)	1978-09-27
CH627170A5 (en)	1981-12-31
FI66353B (fi)	1984-06-29
DK146624C (da)	1984-05-07
CH627171A5 (en)	1981-12-31
MX4722E (es)	1982-08-13
IE46612L (en)	1978-06-20
ATA299780A (de)	1980-12-15
FR2421887A1 (fr)	1979-11-02
AT363074B (de)	1981-07-10
DK566277A (da)	1978-06-21
DE2756852A1 (de)	1978-06-22
AT363071B (de)	1981-07-10
PT67431A (en)	1978-01-01
PH15728A (en)	1983-03-18
IL53498A0 (en)	1978-01-31
JPS6145618B2 (de)	1986-10-08
LU78723A1 (de)	1978-07-11
AU511482B2 (en)	1980-08-21
BE862038A (fr)	1978-06-20
SE443560B (sv)	1986-03-03
PT67431B (en)	1979-05-23
FI66353C (fi)	1984-10-10
ES473365A1 (es)	1979-04-16
ES473366A1 (es)	1979-04-16
CH627451A5 (en)	1982-01-15
NO147108B (no)	1982-10-25
ES473364A1 (es)	1979-04-16
ATA902077A (de)	1980-12-15
AR214655A1 (es)	1979-07-13
SE7714461L (sv)	1978-06-21
HK36785A (en)	1985-05-17
NL9002188A (nl)	1991-03-01
ES473367A1 (es)	1979-05-01
NZ185811A (en)	1980-08-26
JPS5377059A (en)	1978-07-08
ES465206A1 (es)	1979-01-01
CA1098527A (en)	1981-03-31
FI773836A7 (fi)	1978-06-21
ES473376A1 (es)	1979-04-16

Legal Events

Date	Code	Title	Description
1991-08-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0042781B1 (de)	1985-03-06	1-(4- Chinolyl), 2- oder 3- (2- oder 3-piperidyl oder pyrrolidinyl)-Äthanon oder -Propanon, Verfahren zu seiner Herstellung und seine Anwendung als Arzneimittel
EP0373998A1 (de)	1990-06-20	Propenonoximether, Verfahren zu dessen Herstellung sowie diese enthaltende Arzneinmittel
EP0040591A1 (de)	1981-11-25	Pyridoxin-Derivate, Verfahren zu ihrer Herstellung und ihre therapeutische Verwendung
EP0740654A1 (de)	1996-11-06	Monoamin oxydase b hemmende verbidungen verfahren zu ihrer herstellung un ihrer verwendung
FR2496102A1 (fr)	1982-06-18	Benzopyranes 7-substitues, leur preparation et leur application en tant que medicaments
EP0566445B1 (de)	1996-02-07	Indan-1,3-Dion und Indan-1,2,3-Trionderivate, Verfahren zu ihrer Herstellung und ihre therapeutische Verwendung
EP0269599B1 (de)	1993-12-15	Substituierte 1H-Imidazole
BE1009852A3 (fr)	1997-10-07	Derives 1-[2(vinyl-substitues)]-3-4-dihydro-5h-2,3-benzodiazepine.
CH626067A5 (en)	1981-10-30	Process for the preparation of 1-(lower aminoalkyl)-3,4-diphenyl-1H-pyrazoles
FR2526434A1 (fr)	1983-11-10	Nouveaux azepino-indoles, leur preparation et leur utilisation comme medicaments
EP0117196B1 (de)	1986-07-30	N-Iminopyridinium-Betain-Derivate, ihre Herstellung und ihre Verwendung als Arzneimittel
US4182895A (en)	1980-01-08	1-Amino-lower-alkyl-3,4-diphenyl-1H-pyrazoles
CA2045849A1 (fr)	1991-12-30	Derives d'oxazolo pyridines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
EP0151140B1 (de)	1986-12-03	Salz von 2-piperazinopyrimidin, verfahren zu seiner herstellung und dieses enthaltende pharmazeutische zusammenstellungen
EP0220112B1 (de)	1992-04-08	Durch (omega-Amino)-alkanolgruppen substituierte aromatische Derivate mit Antimikrobenwirkung und diese enthaltende Zusammensetzungen
EP0061406B1 (de)	1984-06-13	Benzamido-alkyl-hydroxamsäurederivate, Verfahren zu ihrer Herstellung und pharmazeutische Mittel
EP0170549B1 (de)	1989-01-25	4,5,6,7-Tetrahydrofuro- oder 1H-Pyrrolo [2,3-c]pyridinderivate, ihre Herstellung und therapeutische Verwendung
DD144764A5 (de)	1980-11-05	Verfahren zur herstellung von r-n-(2-phenyl-2-hydroxyethyl)-3-phenylpropylaminen
EP0107536B1 (de)	1986-05-28	Benzo- und Thieno-1,2,3-triazin-4-one, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
FR2493313A1 (fr)	1982-05-07	Pyridinyl-amino-phenols, leur preparation et leur utilisation comme agents cardiotoniques
EP0244318A1 (de)	1987-11-04	N-[(Trimethoxy-2,4,6-benzoyl)-3-propyl]piperidin-Derivate, Verfahren zu ihrer Herstellung und deren Anwendung als Heilmittel
JPS6112689A (ja)	1986-01-21	環式アミド、その製法及び該化合物を含有する糖尿病及びガラクトース血症の合併症を治療又は予防するための製薬的組成物
BE629008A (de)
BE877327A (fr)	1979-12-28	Octahydro-pyrazolo (3,4-g) quinoleines et leur utilisation therapeutique
DE1468022C (de)