HU192023B - Process for production of 2,4-dihydro-5-/substituated phenyl/-4,4/double substituated/-3h-pirasole-3-ons - Google Patents
Process for production of 2,4-dihydro-5-/substituated phenyl/-4,4/double substituated/-3h-pirasole-3-ons Download PDFInfo
- Publication number
- HU192023B HU192023B HU841975A HU197584A HU192023B HU 192023 B HU192023 B HU 192023B HU 841975 A HU841975 A HU 841975A HU 197584 A HU197584 A HU 197584A HU 192023 B HU192023 B HU 192023B
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- HU
- Hungary
- Prior art keywords
- formula
- priority
- preparation
- phenyl
- dihydro
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 238000002360 preparation method Methods 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- -1 1-imidazolyl Chemical group 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 3
- ONJLHCGUQUGAOA-UHFFFAOYSA-N 4,4-dimethyl-3-[4-(1,2,4-triazol-1-yl)phenyl]-1h-pyrazol-5-one Chemical compound CC1(C)C(=O)NN=C1C1=CC=C(N2N=CN=C2)C=C1 ONJLHCGUQUGAOA-UHFFFAOYSA-N 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 2
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical group [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000001077 hypotensive effect Effects 0.000 claims 1
- 210000004165 myocardium Anatomy 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000003177 cardiotonic effect Effects 0.000 abstract description 3
- 239000002220 antihypertensive agent Substances 0.000 abstract description 2
- 229940030600 antihypertensive agent Drugs 0.000 abstract description 2
- 239000000496 cardiotonic agent Substances 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 18
- 239000007787 solid Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000036772 blood pressure Effects 0.000 description 5
- 230000002107 myocardial effect Effects 0.000 description 5
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229960001412 pentobarbital Drugs 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 206010020772 Hypertension Diseases 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 210000005240 left ventricle Anatomy 0.000 description 3
- WRGLZAJBHUOPFO-UHFFFAOYSA-N methyl 3-oxo-3-phenylpropanoate Chemical class COC(=O)CC(=O)C1=CC=CC=C1 WRGLZAJBHUOPFO-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- JNYGXLIZNLMWCF-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-4,4-dimethyl-1h-pyrazol-5-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=NNC(=O)C1(C)C JNYGXLIZNLMWCF-UHFFFAOYSA-N 0.000 description 2
- SLBCXLQHWKXNIC-UHFFFAOYSA-N 3-(4-imidazol-1-ylphenyl)-4,4-dimethyl-1h-pyrazol-5-one Chemical compound CC1(C)C(=O)NN=C1C1=CC=C(N2C=NC=C2)C=C1 SLBCXLQHWKXNIC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 210000000709 aorta Anatomy 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 210000001105 femoral artery Anatomy 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 230000002861 ventricular Effects 0.000 description 2
- ZDPAWHACYDRYIW-UHFFFAOYSA-N 1-(4-fluorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(F)C=C1 ZDPAWHACYDRYIW-UHFFFAOYSA-N 0.000 description 1
- FYLGZBNNVGZPIW-UHFFFAOYSA-N 1-[4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1CCC2(OCCO2)CC1 FYLGZBNNVGZPIW-UHFFFAOYSA-N 0.000 description 1
- HDXNSPHRJQVNJM-UHFFFAOYSA-N 3-[4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)phenyl]-4,4-dimethyl-1h-pyrazol-5-one Chemical compound CC1(C)C(=O)NN=C1C1=CC=C(N2CCC3(CC2)OCCO3)C=C1 HDXNSPHRJQVNJM-UHFFFAOYSA-N 0.000 description 1
- ABIDMAPNBMWJSD-UHFFFAOYSA-N 3-[4-(benzimidazol-1-yl)phenyl]-4,4-dimethyl-1h-pyrazol-5-one Chemical compound CC1(C)C(=O)NN=C1C1=CC=C(N2C3=CC=CC=C3N=C2)C=C1 ABIDMAPNBMWJSD-UHFFFAOYSA-N 0.000 description 1
- HXUIDZOMTRMIOE-UHFFFAOYSA-N 3-oxo-3-phenylpropionic acid Chemical class OC(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-N 0.000 description 1
- QRCHYGHUIAGFIJ-UHFFFAOYSA-N 4,4-dimethyl-3-[4-(4,5,6,7-tetrahydrobenzimidazol-1-yl)phenyl]-1h-pyrazol-5-one Chemical compound CC1(C)C(=O)NN=C1C1=CC=C(N2C=3CCCCC=3N=C2)C=C1 QRCHYGHUIAGFIJ-UHFFFAOYSA-N 0.000 description 1
- QENKQAZIVJLLCS-UHFFFAOYSA-N 4,4-dimethyl-3-phenyl-1h-pyrazol-5-one Chemical compound CC1(C)C(=O)NN=C1C1=CC=CC=C1 QENKQAZIVJLLCS-UHFFFAOYSA-N 0.000 description 1
- YJFMNQSLQFRSJR-UHFFFAOYSA-N 4-ethyl-3-(4-imidazol-1-ylphenyl)-4-methyl-1h-pyrazol-5-one Chemical compound CCC1(C)C(=O)NN=C1C1=CC=C(N2C=NC=C2)C=C1 YJFMNQSLQFRSJR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000005947 Dimethoate Substances 0.000 description 1
- 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 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- HBTCIXRKQDJBMS-UHFFFAOYSA-N methyl 2,2-dimethyl-3-oxo-3-phenylpropanoate Chemical class COC(=O)C(C)(C)C(=O)C1=CC=CC=C1 HBTCIXRKQDJBMS-UHFFFAOYSA-N 0.000 description 1
- DUMQFLGJMUWUPV-UHFFFAOYSA-N methyl 2-(3,4-dimethoxyphenyl)propanoate Chemical compound COC(=O)C(C)C1=CC=C(OC)C(OC)=C1 DUMQFLGJMUWUPV-UHFFFAOYSA-N 0.000 description 1
- HVQVHXKJOPBUNV-UHFFFAOYSA-N methyl 2-(4-imidazol-1-ylbenzoyl)-2-methylbutanoate Chemical compound C1=CC(C(=O)C(C)(C(=O)OC)CC)=CC=C1N1C=NC=C1 HVQVHXKJOPBUNV-UHFFFAOYSA-N 0.000 description 1
- KUSJBCBZGGAXBX-UHFFFAOYSA-N methyl 3-(3,4-dimethoxyphenyl)-3-oxopropanoate Chemical compound COC(=O)CC(=O)C1=CC=C(OC)C(OC)=C1 KUSJBCBZGGAXBX-UHFFFAOYSA-N 0.000 description 1
- BHGLGKIQCFIEPX-UHFFFAOYSA-N methyl 3-[4-(benzimidazol-1-yl)phenyl]-3-oxopropanoate Chemical compound C1=CC(C(=O)CC(=O)OC)=CC=C1N1C2=CC=CC=C2N=C1 BHGLGKIQCFIEPX-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011707 mineral Substances 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- 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
- C07D231/14—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
-
- 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
-
- 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
- C07D231/14—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/497,316 US4526982A (en) | 1983-05-23 | 1983-05-23 | 2,4-Dihydro-5-[(substituted)phenyl]-4,4-disubstituted-3H-pyrazol-3-ones |
| US06/586,430 US4550119A (en) | 1983-05-23 | 1984-03-12 | 2,4-Dihydro-5-[(substituted)phenyl]-4,4-disubstituted-3H-pyrazol-3-ones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT34971A HUT34971A (en) | 1985-05-28 |
| HU192023B true HU192023B (en) | 1987-04-28 |
Family
ID=27052456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU841975A HU192023B (en) | 1983-05-23 | 1984-05-22 | Process for production of 2,4-dihydro-5-/substituated phenyl/-4,4/double substituated/-3h-pirasole-3-ons |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4550119A (en, 2012) |
| EP (1) | EP0126651A3 (en, 2012) |
| KR (1) | KR840009298A (en, 2012) |
| AU (1) | AU567345B2 (en, 2012) |
| CA (1) | CA1215982A (en, 2012) |
| DK (1) | DK250984A (en, 2012) |
| ES (1) | ES8601143A1 (en, 2012) |
| FI (1) | FI842005A7 (en, 2012) |
| GR (1) | GR82359B (en, 2012) |
| HU (1) | HU192023B (en, 2012) |
| IL (1) | IL71841A (en, 2012) |
| NO (1) | NO842028L (en, 2012) |
| NZ (1) | NZ208244A (en, 2012) |
| PH (1) | PH19768A (en, 2012) |
| PT (1) | PT78623B (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3310197A1 (de) * | 1983-03-21 | 1984-09-27 | A. Nattermann & Cie GmbH, 5000 Köln | Substituierte 3-mercapto-pyridazine und deren 3-alkylthioderivate sowie verfahren zu ihrer herstellung |
| ZA859091B (en) * | 1984-12-24 | 1987-07-29 | Warner Lambert Co | Novel 6-substituted-2 (1h)-quinolinones and related compounds having use as cardiotonic,anti-hypertensive,and anti-thrombotic agents |
| US4840955A (en) * | 1984-12-24 | 1989-06-20 | Warner-Lambert Company | 6-substituted-2(1H)-quinolinones and related compounds having use as cardiotonic, antihypertensive, and antithrombotic agents |
| GB8502267D0 (en) * | 1985-01-30 | 1985-02-27 | Pfizer Ltd | Quinolone inotropic agents |
| USRE35801E (en) * | 1985-05-20 | 1998-05-19 | Mitsubishi Chemical Corporation | Prophylactic and therapeutic composition for circulatory disorders and method of treatment |
| DK169672B1 (da) * | 1985-05-20 | 1995-01-09 | Mitsubishi Chem Ind | Farmaceutiske præparater indeholdende pyrazolonderivater som aktiv bestanddel og anvendelsen af pyrazolonderivater til fremstilling af farmaceutiske præparater |
| US4666913A (en) * | 1985-11-22 | 1987-05-19 | William H. Rorer, Inc. | Hydroxy and aminothiazolyl-benzodiazinone compounds, cardiotonic compositions including the same, and their uses |
| DK40192D0 (da) * | 1992-03-26 | 1992-03-26 | Neurosearch As | Imidazolforbindelser, deres fremstilling og anvendelse |
| UA100019C2 (en) | 2007-05-16 | 2012-11-12 | Никомед Гмбх | Pyrazolone derivatives as pde4 inhibitors |
| AR074318A1 (es) | 2008-11-14 | 2011-01-05 | Nycomed Gmbh | Derivados heterociclicos de pirazolona, composiciones farmaceuticas que los contienen y uso de los mismos para el tratamiento de enfermedades de las vias respiratorias. |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL286908A (en, 2012) * | 1961-12-19 | |||
| GB962533A (en) * | 1962-04-24 | 1964-07-01 | Imp Chemical Industi Australia | Anthelmintic compositions |
| DE2828529A1 (de) * | 1978-06-29 | 1980-01-17 | Kali Chemie Pharma Gmbh | Neue 5-phenylpyrazol-derivate, verfahren zu deren herstellung und arzneimittel |
| SE8003277L (sv) * | 1979-05-04 | 1980-11-05 | Continental Pharma | Bensimidazolderivat, deras framstellning och anvendning samt kompositioner innehallande dessa derivat |
| FR2479219A1 (fr) * | 1980-04-01 | 1981-10-02 | Nativelle Sa Ets | Amino-alcoxy pyrazoles, procede pour leur preparation, et medicaments les contenant |
| FR2513996A1 (fr) * | 1981-10-02 | 1983-04-08 | Nativelle Sa Ets | Derives du pyrazole, procede pour leur preparation et application en therapeutique |
-
1984
- 1984-03-12 US US06/586,430 patent/US4550119A/en not_active Expired - Fee Related
- 1984-05-03 CA CA000453446A patent/CA1215982A/en not_active Expired
- 1984-05-15 IL IL71841A patent/IL71841A/xx not_active IP Right Cessation
- 1984-05-16 KR KR1019840002637A patent/KR840009298A/ko not_active Abandoned
- 1984-05-18 FI FI842005A patent/FI842005A7/fi not_active Application Discontinuation
- 1984-05-21 PT PT78623A patent/PT78623B/pt unknown
- 1984-05-21 AU AU28440/84A patent/AU567345B2/en not_active Ceased
- 1984-05-21 PH PH30705A patent/PH19768A/en unknown
- 1984-05-22 NZ NZ208244A patent/NZ208244A/xx unknown
- 1984-05-22 NO NO842028A patent/NO842028L/no unknown
- 1984-05-22 DK DK250984A patent/DK250984A/da not_active Application Discontinuation
- 1984-05-22 ES ES532689A patent/ES8601143A1/es not_active Expired
- 1984-05-22 GR GR74794A patent/GR82359B/el unknown
- 1984-05-22 HU HU841975A patent/HU192023B/hu unknown
- 1984-05-22 EP EP84303456A patent/EP0126651A3/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| AU2844084A (en) | 1984-11-29 |
| EP0126651A2 (en) | 1984-11-28 |
| CA1215982A (en) | 1986-12-30 |
| IL71841A (en) | 1987-10-20 |
| ES532689A0 (es) | 1985-10-16 |
| DK250984D0 (da) | 1984-05-22 |
| PH19768A (en) | 1986-06-27 |
| US4550119A (en) | 1985-10-29 |
| AU567345B2 (en) | 1987-11-19 |
| NZ208244A (en) | 1986-10-08 |
| NO842028L (no) | 1984-11-26 |
| FI842005A0 (fi) | 1984-05-18 |
| IL71841A0 (en) | 1984-09-30 |
| KR840009298A (ko) | 1984-12-26 |
| EP0126651A3 (en) | 1989-02-08 |
| GR82359B (en, 2012) | 1984-12-13 |
| HUT34971A (en) | 1985-05-28 |
| DK250984A (da) | 1984-11-24 |
| FI842005A7 (fi) | 1984-11-24 |
| PT78623B (en) | 1986-07-17 |
| PT78623A (en) | 1984-06-01 |
| ES8601143A1 (es) | 1985-10-16 |
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