NL8001349A - Nieuwe mercaptoacyldihydropyrazoolderivaten, werkwijze voor de bereiding daarvan, farmaceutische preparaten die deze bevatten, alsmede werkwijze voor het behande- len van zoogdieren. - Google Patents
Nieuwe mercaptoacyldihydropyrazoolderivaten, werkwijze voor de bereiding daarvan, farmaceutische preparaten die deze bevatten, alsmede werkwijze voor het behande- len van zoogdieren. Download PDFInfo
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- NL8001349A NL8001349A NL8001349A NL8001349A NL8001349A NL 8001349 A NL8001349 A NL 8001349A NL 8001349 A NL8001349 A NL 8001349A NL 8001349 A NL8001349 A NL 8001349A NL 8001349 A NL8001349 A NL 8001349A
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- Netherlands
- Prior art keywords
- formula
- hydrogen
- alkyl
- compound according
- aryl
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 28
- 238000002360 preparation method Methods 0.000 title claims description 5
- 241000124008 Mammalia Species 0.000 title claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 3
- KEQTWHPMSVAFDA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical class C1NNC=C1 KEQTWHPMSVAFDA-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001447 alkali salts Chemical class 0.000 claims description 5
- 230000036772 blood pressure Effects 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 239000000047 product Substances 0.000 description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- -1 nitro, amino Chemical group 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 4
- VBNSXUOMQDHOKL-UHFFFAOYSA-N 3-phenyl-4,5-dihydro-1h-pyrazole-5-carboxylic acid Chemical compound N1C(C(=O)O)CC(C=2C=CC=CC=2)=N1 VBNSXUOMQDHOKL-UHFFFAOYSA-N 0.000 description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
- 101800000734 Angiotensin-1 Proteins 0.000 description 4
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- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 4
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
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- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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- 102000005862 Angiotensin II Human genes 0.000 description 3
- 101800000733 Angiotensin-2 Proteins 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
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- 229950006323 angiotensin ii Drugs 0.000 description 3
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- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
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- 238000010992 reflux Methods 0.000 description 3
- XEYWOETXQNDSED-UHFFFAOYSA-N s-(3-chloro-3-oxopropyl) ethanethioate Chemical compound CC(=O)SCCC(Cl)=O XEYWOETXQNDSED-UHFFFAOYSA-N 0.000 description 3
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- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
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- LOEWUOVQQXKRDS-UHFFFAOYSA-N 3-(4-methoxyphenyl)-4,5-dihydro-1h-pyrazole-5-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=NNC(C(O)=O)C1 LOEWUOVQQXKRDS-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
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- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
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- VQVQEUFKSRHRCT-AATRIKPKSA-N (e)-4-(4-chlorophenyl)-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)C1=CC=C(Cl)C=C1 VQVQEUFKSRHRCT-AATRIKPKSA-N 0.000 description 1
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- ZDPAWHACYDRYIW-UHFFFAOYSA-N 1-(4-fluorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(F)C=C1 ZDPAWHACYDRYIW-UHFFFAOYSA-N 0.000 description 1
- VAHWJEAMIHUISN-UHFFFAOYSA-N 2-(3-acetylsulfanylpropanoyl)-5-(2-methylphenyl)-3,4-dihydropyrazole-3-carboxylic acid Chemical compound C(C)(=O)SCCC(=O)N1N=C(CC1C(=O)O)C1=C(C=CC=C1)C VAHWJEAMIHUISN-UHFFFAOYSA-N 0.000 description 1
- PSTGHLQZLYEKDB-UHFFFAOYSA-N 2-(3-acetylsulfanylpropanoyl)-5-(3-chlorophenyl)-3,4-dihydropyrazole-3-carboxylic acid Chemical compound C(C)(=O)SCCC(=O)N1N=C(CC1C(=O)O)C1=CC(=CC=C1)Cl PSTGHLQZLYEKDB-UHFFFAOYSA-N 0.000 description 1
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 1
- HMROYASMQXLLPA-UHFFFAOYSA-N 3-(2-methylphenyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid Chemical compound CC1=C(C=CC=C1)C1=NNC(C1)C(=O)O HMROYASMQXLLPA-UHFFFAOYSA-N 0.000 description 1
- BABZLKSKIRICSX-UHFFFAOYSA-N 3-(3,4-dimethylphenyl)-4,5-dihydro-1h-pyrazole-5-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1=NNC(C(O)=O)C1 BABZLKSKIRICSX-UHFFFAOYSA-N 0.000 description 1
- FUVFAUBWEXSLEY-UHFFFAOYSA-N 3-(3,4-dimethylphenyl)prop-2-enoic acid Chemical compound CC1=CC=C(C=CC(O)=O)C=C1C FUVFAUBWEXSLEY-UHFFFAOYSA-N 0.000 description 1
- JHSUAABTVKYNDK-UHFFFAOYSA-N 3-(3-chlorophenyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid Chemical compound ClC=1C=C(C=CC=1)C1=NNC(C1)C(=O)O JHSUAABTVKYNDK-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- IEDKTEKUQAVTCB-UHFFFAOYSA-N 5-(2-methylphenyl)-2-(3-sulfanylpropanoyl)-3,4-dihydropyrazole-3-carboxylic acid Chemical compound SCCC(=O)N1N=C(CC1C(=O)O)C1=C(C=CC=C1)C IEDKTEKUQAVTCB-UHFFFAOYSA-N 0.000 description 1
- ISGYXALIWIQOTF-UHFFFAOYSA-N 5-(3-chlorophenyl)-2-(3-sulfanylpropanoyl)-3,4-dihydropyrazole-3-carboxylic acid Chemical compound SCCC(=O)N1N=C(CC1C(=O)O)C1=CC(=CC=C1)Cl ISGYXALIWIQOTF-UHFFFAOYSA-N 0.000 description 1
- QUUYOHQKLWWAFX-UHFFFAOYSA-N 5-(4-fluorophenyl)-2-(3-sulfanylpropanoyl)-3,4-dihydropyrazole-3-carboxylic acid Chemical compound SCCC(=O)N1C(C(=O)O)CC(C=2C=CC(F)=CC=2)=N1 QUUYOHQKLWWAFX-UHFFFAOYSA-N 0.000 description 1
- XEGYXCYHIUXTJP-UHFFFAOYSA-N 5-(4-hydroxyphenyl)-2-(3-sulfanylpropanoyl)-3,4-dihydropyrazole-3-carboxylic acid Chemical compound SCCC(=O)N1N=C(CC1C(=O)O)C1=CC=C(C=C1)O XEGYXCYHIUXTJP-UHFFFAOYSA-N 0.000 description 1
- VMQSKGFPGFMTBI-UHFFFAOYSA-N 5-(4-methoxyphenyl)-2-(3-sulfanylpropanoyl)-3,4-dihydropyrazole-3-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=NN(C(=O)CCS)C(C(O)=O)C1 VMQSKGFPGFMTBI-UHFFFAOYSA-N 0.000 description 1
- VAVDIAWVXWKQQM-UHFFFAOYSA-N 5-(4-methylphenyl)-2-(3-sulfanylpropanoyl)-3,4-dihydropyrazole-3-carboxylic acid Chemical compound SCCC(=O)N1N=C(CC1C(=O)O)C1=CC=C(C=C1)C VAVDIAWVXWKQQM-UHFFFAOYSA-N 0.000 description 1
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- 150000001721 carbon Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- ZQSIJRDFPHDXIC-UHFFFAOYSA-N daidzein Chemical class C1=CC(O)=CC=C1C1=COC2=CC(O)=CC=C2C1=O ZQSIJRDFPHDXIC-UHFFFAOYSA-N 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 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
- XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical class C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical class [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000003441 thioacyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000005406 washing 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
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1854879 | 1979-03-08 | ||
| US06/018,548 US4211786A (en) | 1979-03-08 | 1979-03-08 | Mercaptoacyldihydropyrazole carboxylic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8001349A true NL8001349A (nl) | 1980-09-10 |
Family
ID=21788501
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8001349A NL8001349A (nl) | 1979-03-08 | 1980-03-06 | Nieuwe mercaptoacyldihydropyrazoolderivaten, werkwijze voor de bereiding daarvan, farmaceutische preparaten die deze bevatten, alsmede werkwijze voor het behande- len van zoogdieren. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4211786A (online.php) |
| JP (1) | JPS55122766A (online.php) |
| AU (1) | AU534582B2 (online.php) |
| BE (1) | BE882133A (online.php) |
| CA (1) | CA1137497A (online.php) |
| CH (1) | CH645630A5 (online.php) |
| DE (1) | DE3008904A1 (online.php) |
| DK (1) | DK99980A (online.php) |
| FR (1) | FR2450820A1 (online.php) |
| GB (1) | GB2048850B (online.php) |
| IE (1) | IE49541B1 (online.php) |
| IT (1) | IT1127384B (online.php) |
| LU (1) | LU82223A1 (online.php) |
| NL (1) | NL8001349A (online.php) |
| SE (1) | SE450382B (online.php) |
| ZA (1) | ZA801016B (online.php) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA794723B (en) * | 1978-09-11 | 1980-08-27 | Univ Miami | Anti-hypertensive agents |
| US4331806A (en) * | 1979-07-30 | 1982-05-25 | E. R. Squibb & Sons, Inc. | Dithioacyldihydropyrazole carboxylic acid derivatives |
| US4288368A (en) * | 1979-07-30 | 1981-09-08 | E. R. Squibb & Sons, Inc. | Dithioacylproline derivatives |
| CA1156236A (en) * | 1979-10-25 | 1983-11-01 | George C. Rovnyak | Mercaptoacyldihydropyrazole carboxylic acid derivatives |
| US4266065A (en) * | 1980-04-14 | 1981-05-05 | E. R. Squibb & Sons, Inc. | Mercaptoacyldihydropyrazole carboxylic acid derivatives |
| US4254267A (en) * | 1979-10-25 | 1981-03-03 | E. R. Squibb & Sons, Inc. | Mercaptoacyldihydropyrazole carboxylic acid derivatives |
| US4692458A (en) * | 1980-03-05 | 1987-09-08 | University Of Miami | Anti-hypertensive agents |
| US4312990A (en) * | 1980-09-11 | 1982-01-26 | E. R. Squibb & Sons, Inc. | 1-Mercaptoacyl-3-[(aminosulfonyl) phenyl]-4,5-dihydro-1H-pyrazole-5-carboxylic acid |
| US4371526A (en) * | 1981-08-21 | 1983-02-01 | E. R. Squibb & Sons, Inc. | Phosphinylalkanoyl substituted 4,5-dihydropyrazole-5-carboxylic acid derivatives and hypotensive method and composition |
| JPS58133376U (ja) * | 1982-03-05 | 1983-09-08 | 吉原 靖人 | バツテイング練習用バツト |
| US4470973A (en) * | 1982-07-19 | 1984-09-11 | E. R. Squibb & Sons, Inc. | Substituted peptide compounds |
| US4742067A (en) * | 1982-07-22 | 1988-05-03 | E. R. Squibb & Sons, Inc. | Acylalkylaminocarbonyl substituted amino and imino acid compounds |
| US4621092A (en) * | 1982-07-22 | 1986-11-04 | E. R. Squibb & Sons, Inc. | Substituted proline compounds, composition and method of use |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4105776A (en) * | 1976-06-21 | 1978-08-08 | E. R. Squibb & Sons, Inc. | Proline derivatives and related compounds |
| US4046889A (en) * | 1976-02-13 | 1977-09-06 | E. R. Squibb & Sons, Inc. | Azetidine-2-carboxylic acid derivatives |
| US4053651A (en) * | 1976-05-10 | 1977-10-11 | E. R. Squibb & Sons, Inc. | Compounds and method for alleviating angiotensin related hypertension |
| ZA777062B (en) * | 1976-12-03 | 1979-02-28 | Squibb & Sons Inc | Derivatives of thiazolidinecarboxylic acids and related acids |
| US4129566A (en) * | 1978-02-15 | 1978-12-12 | E. R. Squibb & Sons, Inc. | Derivatives of dehydrocyclicimino acids |
-
1979
- 1979-03-08 US US06/018,548 patent/US4211786A/en not_active Expired - Lifetime
-
1980
- 1980-02-15 CA CA000345726A patent/CA1137497A/en not_active Expired
- 1980-02-22 AU AU55822/80A patent/AU534582B2/en not_active Ceased
- 1980-02-22 ZA ZA00801016A patent/ZA801016B/xx unknown
- 1980-03-03 IT IT48062/80A patent/IT1127384B/it active
- 1980-03-05 LU LU82223A patent/LU82223A1/de unknown
- 1980-03-06 IE IE449/80A patent/IE49541B1/en not_active IP Right Cessation
- 1980-03-06 NL NL8001349A patent/NL8001349A/nl not_active Application Discontinuation
- 1980-03-06 CH CH177180A patent/CH645630A5/de not_active IP Right Cessation
- 1980-03-07 DK DK99980A patent/DK99980A/da not_active Application Discontinuation
- 1980-03-07 DE DE19803008904 patent/DE3008904A1/de not_active Ceased
- 1980-03-07 BE BE0/199718A patent/BE882133A/fr not_active IP Right Cessation
- 1980-03-07 FR FR8005217A patent/FR2450820A1/fr active Granted
- 1980-03-07 SE SE8001818A patent/SE450382B/sv not_active IP Right Cessation
- 1980-03-07 GB GB8007914A patent/GB2048850B/en not_active Expired
- 1980-03-08 JP JP2971480A patent/JPS55122766A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IT1127384B (it) | 1986-05-21 |
| LU82223A1 (de) | 1980-09-24 |
| IE49541B1 (en) | 1985-10-30 |
| DE3008904A1 (de) | 1980-09-18 |
| FR2450820A1 (fr) | 1980-10-03 |
| AU5582280A (en) | 1980-09-11 |
| IT8048062A0 (it) | 1980-03-03 |
| SE450382B (sv) | 1987-06-22 |
| IE800449L (en) | 1980-09-08 |
| CA1137497A (en) | 1982-12-14 |
| JPS55122766A (en) | 1980-09-20 |
| FR2450820B1 (online.php) | 1983-04-22 |
| JPH0141628B2 (online.php) | 1989-09-06 |
| US4211786A (en) | 1980-07-08 |
| GB2048850B (en) | 1983-04-27 |
| CH645630A5 (de) | 1984-10-15 |
| BE882133A (fr) | 1980-09-08 |
| DK99980A (da) | 1980-09-09 |
| GB2048850A (en) | 1980-12-17 |
| AU534582B2 (en) | 1984-02-09 |
| SE8001818L (sv) | 1980-09-09 |
| ZA801016B (en) | 1981-02-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BV | The patent application has lapsed |