SK284167B6 - Derivát arylalkylpyridazinónu, spôsob jeho prípravy, použitie derivátu arylalkylpyridazinónu, farmaceutický prostriedok, ktorý ho obsahuje, a spôsob prípravy farmaceutického prostriedku - Google Patents
Derivát arylalkylpyridazinónu, spôsob jeho prípravy, použitie derivátu arylalkylpyridazinónu, farmaceutický prostriedok, ktorý ho obsahuje, a spôsob prípravy farmaceutického prostriedku Download PDFInfo
- Publication number
- SK284167B6 SK284167B6 SK487-96A SK48796A SK284167B6 SK 284167 B6 SK284167 B6 SK 284167B6 SK 48796 A SK48796 A SK 48796A SK 284167 B6 SK284167 B6 SK 284167B6
- Authority
- SK
- Slovakia
- Prior art keywords
- tetrahydropyridazin
- ethyl
- chloride
- dimethoxyphenyl
- methoxyphenyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 11
- -1 methylenedioxy Chemical group 0.000 claims abstract description 259
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 239000000460 chlorine Substances 0.000 claims abstract description 11
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 11
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000011737 fluorine Substances 0.000 claims abstract description 7
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims abstract description 6
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims abstract description 6
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- YYLMPPQOOUHPPJ-UHFFFAOYSA-N n-[3-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC1=CC=CC(NC(C)=O)=C1 YYLMPPQOOUHPPJ-UHFFFAOYSA-N 0.000 claims description 2
- FCEFLSGAPFCWGS-UHFFFAOYSA-N n-[3-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]methanesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC1=CC=CC(NS(C)(=O)=O)=C1 FCEFLSGAPFCWGS-UHFFFAOYSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
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- NIHJXZMNNAHEEV-UHFFFAOYSA-N ethyl n-[4-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)CC(CC)C(C=2C=C(OC)C(OC)=CC=2)=N1 NIHJXZMNNAHEEV-UHFFFAOYSA-N 0.000 claims 1
- RQPOEGOXCVKURG-UHFFFAOYSA-N ethyl n-[4-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)CCC(C=2C=C(OC)C(OC)=CC=2)=N1 RQPOEGOXCVKURG-UHFFFAOYSA-N 0.000 claims 1
- VZVHHKYHUMMCRW-UHFFFAOYSA-N methyl n-[4-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)OC)C=C1 VZVHHKYHUMMCRW-UHFFFAOYSA-N 0.000 claims 1
- XDGXAZPROPKMKW-UHFFFAOYSA-N n-[4-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-2,2,2-trifluoroacetamide Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)C(F)(F)F)C=C1 XDGXAZPROPKMKW-UHFFFAOYSA-N 0.000 claims 1
- YMAJLELSVNAWDQ-UHFFFAOYSA-N n-[4-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]butanamide Chemical compound C1=CC(NC(=O)CCC)=CC=C1CN1C(=O)CC(CC)C(C=2C=C(OC)C(OC)=CC=2)=N1 YMAJLELSVNAWDQ-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 abstract description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 4
- 208000006673 asthma Diseases 0.000 abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 2
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract description 2
- 101100240516 Caenorhabditis elegans nhr-10 gene Proteins 0.000 abstract 1
- 230000000979 retarding effect Effects 0.000 abstract 1
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- 238000006243 chemical reaction Methods 0.000 description 20
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 10
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- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 8
- ZXUQEPZWVQIOJE-UHFFFAOYSA-N methyl 2-chloro-2-oxoacetate Chemical compound COC(=O)C(Cl)=O ZXUQEPZWVQIOJE-UHFFFAOYSA-N 0.000 description 8
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 8
- SHMNLEQWIMKCQA-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoyl chloride Chemical compound FC(F)(F)C(F)(F)C(Cl)=O SHMNLEQWIMKCQA-UHFFFAOYSA-N 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 7
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- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 6
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- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 4
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- KXSOQZRWQCSFJG-UHFFFAOYSA-N methyl 2-[3-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]anilino]-2-oxoacetate Chemical compound COC(=O)C(=O)NC1=CC=CC(CN2C(CCC(=N2)C=2C=C(OC)C(OC)=CC=2)=O)=C1 KXSOQZRWQCSFJG-UHFFFAOYSA-N 0.000 description 1
- GVAAJIYLDBOALI-UHFFFAOYSA-N methyl 2-[4-[2-[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]ethyl]anilino]-2-oxoacetate Chemical compound C1=CC(NC(=O)C(=O)OC)=CC=C1CCN1C(=O)CCC(C=2C=C(OC)C(OC)=CC=2)=N1 GVAAJIYLDBOALI-UHFFFAOYSA-N 0.000 description 1
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- HVQLONHFPXVKGM-UHFFFAOYSA-N methyl 2-[4-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]anilino]-2-oxoacetate Chemical compound C1=CC(NC(=O)C(=O)OC)=CC=C1CN1C(=O)CCC(C=2C=C(OC)C(OC)=CC=2)=N1 HVQLONHFPXVKGM-UHFFFAOYSA-N 0.000 description 1
- PNAAXTXDAXPPCR-UHFFFAOYSA-N methyl 2-[4-[[3-(3-cyclopentyloxy-4-methoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]anilino]-2-oxoacetate Chemical compound C1=CC(NC(=O)C(=O)OC)=CC=C1CN1C(=O)CCC(C=2C=C(OC3CCCC3)C(OC)=CC=2)=N1 PNAAXTXDAXPPCR-UHFFFAOYSA-N 0.000 description 1
- MTACDBARDPRQMY-UHFFFAOYSA-N methyl 2-[4-[[3-(3-ethoxy-4-methoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]anilino]-2-oxoacetate Chemical compound C1=C(OC)C(OCC)=CC(C=2CCC(=O)N(CC=3C=CC(NC(=O)C(=O)OC)=CC=3)N=2)=C1 MTACDBARDPRQMY-UHFFFAOYSA-N 0.000 description 1
- DRNAKASZNADFQV-UHFFFAOYSA-N methyl 2-[4-[[3-[3-(difluoromethoxy)-4-methoxyphenyl]-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]anilino]-2-oxoacetate Chemical compound N1=C(C=2C=C(OC(F)F)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)C(=O)OC)C=C1 DRNAKASZNADFQV-UHFFFAOYSA-N 0.000 description 1
- QVGFXSAKMWSHSR-UHFFFAOYSA-N methyl n-[3-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(CN2C(CCC(=N2)C=2C=C(OC)C(OC)=CC=2)=O)=C1 QVGFXSAKMWSHSR-UHFFFAOYSA-N 0.000 description 1
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- MNEDWOXTEZAZFU-UHFFFAOYSA-N n-[4-[[4-ethyl-3-[4-(fluoromethoxy)-3-methoxyphenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]methanesulfonamide Chemical compound N1=C(C=2C=C(OC)C(OCF)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NS(C)(=O)=O)C=C1 MNEDWOXTEZAZFU-UHFFFAOYSA-N 0.000 description 1
- ATQQEIMIJRRPOD-UHFFFAOYSA-N n-[4-[[4-ethyl-3-[4-(fluoromethoxy)-3-methoxyphenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]pentanamide Chemical compound C1=CC(NC(=O)CCCC)=CC=C1CN1C(=O)CC(CC)C(C=2C=C(OC)C(OCF)=CC=2)=N1 ATQQEIMIJRRPOD-UHFFFAOYSA-N 0.000 description 1
- WAAIEGWRDLGKMQ-UHFFFAOYSA-N n-[4-[[4-ethyl-3-[4-(fluoromethoxy)-3-methoxyphenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]propanamide Chemical compound N1=C(C=2C=C(OC)C(OCF)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)CC)C=C1 WAAIEGWRDLGKMQ-UHFFFAOYSA-N 0.000 description 1
- GXPGROZYCUDOBK-UHFFFAOYSA-N n-[4-[[4-ethyl-3-[4-methoxy-3-(trifluoromethoxy)phenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-2,2,3,3,3-pentafluoropropanamide Chemical compound N1=C(C=2C=C(OC(F)(F)F)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)C(F)(F)C(F)(F)F)C=C1 GXPGROZYCUDOBK-UHFFFAOYSA-N 0.000 description 1
- DKPLPSVBMQQUHZ-UHFFFAOYSA-N n-[4-[[4-ethyl-3-[4-methoxy-3-(trifluoromethoxy)phenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]hexanamide Chemical compound C1=CC(NC(=O)CCCCC)=CC=C1CN1C(=O)CC(CC)C(C=2C=C(OC(F)(F)F)C(OC)=CC=2)=N1 DKPLPSVBMQQUHZ-UHFFFAOYSA-N 0.000 description 1
- VTFROQVQLSWIEV-UHFFFAOYSA-N n-[4-[[4-ethyl-3-[4-methoxy-3-(trifluoromethoxy)phenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]pentanamide Chemical compound C1=CC(NC(=O)CCCC)=CC=C1CN1C(=O)CC(CC)C(C=2C=C(OC(F)(F)F)C(OC)=CC=2)=N1 VTFROQVQLSWIEV-UHFFFAOYSA-N 0.000 description 1
- JXTICDYPIKTUDJ-UHFFFAOYSA-N n-cyclopentyl-4-[2-[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]ethyl]benzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CCC1=CC=C(C(=O)NC2CCCC2)C=C1 JXTICDYPIKTUDJ-UHFFFAOYSA-N 0.000 description 1
- QKFHZKUWYFXLMS-UHFFFAOYSA-N n-cyclopentyl-4-[[4-ethyl-3-[3-(fluoromethoxy)-4-methoxyphenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]benzamide Chemical compound N1=C(C=2C=C(OCF)C(OC)=CC=2)C(CC)CC(=O)N1CC(C=C1)=CC=C1C(=O)NC1CCCC1 QKFHZKUWYFXLMS-UHFFFAOYSA-N 0.000 description 1
- IAARSOWFPQPFNS-UHFFFAOYSA-N n-cyclopentyl-4-[[4-ethyl-3-[3-methoxy-4-(trifluoromethoxy)phenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]benzamide Chemical compound N1=C(C=2C=C(OC)C(OC(F)(F)F)=CC=2)C(CC)CC(=O)N1CC(C=C1)=CC=C1C(=O)NC1CCCC1 IAARSOWFPQPFNS-UHFFFAOYSA-N 0.000 description 1
- YBOQYBKTBBEBIV-UHFFFAOYSA-N n-cyclopentyl-4-[[4-ethyl-3-[4-(fluoromethoxy)-3-methoxyphenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]benzamide Chemical compound N1=C(C=2C=C(OC)C(OCF)=CC=2)C(CC)CC(=O)N1CC(C=C1)=CC=C1C(=O)NC1CCCC1 YBOQYBKTBBEBIV-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 125000006504 o-cyanobenzyl group Chemical group [H]C1=C([H])C(C#N)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 229940116317 potato starch Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Curing Cements, Concrete, And Artificial Stone (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicinal Preparation (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19514568A DE19514568A1 (de) | 1995-04-20 | 1995-04-20 | Arylalkyl-pyridazinone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK48796A3 SK48796A3 (en) | 1997-02-05 |
| SK284167B6 true SK284167B6 (sk) | 2004-10-05 |
Family
ID=7759974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK487-96A SK284167B6 (sk) | 1995-04-20 | 1996-04-17 | Derivát arylalkylpyridazinónu, spôsob jeho prípravy, použitie derivátu arylalkylpyridazinónu, farmaceutický prostriedok, ktorý ho obsahuje, a spôsob prípravy farmaceutického prostriedku |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US6399611B1 (cs) |
| EP (1) | EP0738715B1 (cs) |
| JP (1) | JP4005157B2 (cs) |
| KR (1) | KR100428879B1 (cs) |
| CN (1) | CN1159299C (cs) |
| AT (1) | ATE231842T1 (cs) |
| AU (1) | AU705025B2 (cs) |
| CA (1) | CA2174472C (cs) |
| CZ (1) | CZ291868B6 (cs) |
| DE (2) | DE19514568A1 (cs) |
| DK (1) | DK0738715T3 (cs) |
| ES (1) | ES2191070T3 (cs) |
| HU (1) | HU226198B1 (cs) |
| NO (1) | NO307931B1 (cs) |
| PT (1) | PT738715E (cs) |
| RU (1) | RU2159236C2 (cs) |
| SI (1) | SI0738715T1 (cs) |
| SK (1) | SK284167B6 (cs) |
| TW (1) | TW475927B (cs) |
| UA (1) | UA43853C2 (cs) |
| ZA (1) | ZA963154B (cs) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19533975A1 (de) * | 1995-09-14 | 1997-03-20 | Merck Patent Gmbh | Arylalkyl-diazinone |
| JP4017214B2 (ja) | 1996-06-11 | 2007-12-05 | 興和創薬株式会社 | ５−フェニル−３−ピリダジノン誘導体 |
| CA2264685C (en) * | 1996-08-27 | 2002-10-15 | Kyoji Noda | 2-phenylmorpholin-5-one derivatives and pharmaceutical composition comprising the same |
| CN1173950C (zh) * | 1998-10-06 | 2004-11-03 | 大日本制药株式会社 | 2,3-二取代的吡啶衍生物、其制备方法、含有其的药物组合物和用于制备中的中间体 |
| DE19850701A1 (de) * | 1998-11-04 | 2000-05-11 | Merck Patent Gmbh | Benzoylpyridazine |
| NZ517166A (en) | 1999-08-21 | 2004-01-30 | Altana Pharma Ag | Synergistic combination of PDE inhibitors and beta 2 adrenoceptor agonists |
| RU2279428C2 (ru) * | 2000-09-18 | 2006-07-10 | Эйсай Ко., Лтд. | Производные пиридазинона и триазинона и их применение в качестве фармацевтических препаратов |
| DE10064997A1 (de) * | 2000-12-23 | 2002-06-27 | Merck Patent Gmbh | Benzoylpyridazine |
| CN1235589C (zh) * | 2001-02-12 | 2006-01-11 | 默克专利股份公司 | 4型磷酸二酯酶抑制剂在制备治疗心肌疾病药物中的应用 |
| US6872382B1 (en) | 2001-05-21 | 2005-03-29 | Alcon, Inc. | Use of selective PDE IV inhibitors to treat dry eye disorders |
| KR20040007583A (ko) * | 2001-05-23 | 2004-01-24 | 다나베 세이야꾸 가부시키가이샤 | 연골 질환의 재생치료용 조성물 |
| WO2002094321A1 (en) | 2001-05-23 | 2002-11-28 | Tanabe Seiyaku Co., Ltd. | Compositions for promoting healing of bone fracture |
| DE10150517A1 (de) * | 2001-10-12 | 2003-04-17 | Merck Patent Gmbh | Verwendung von Phosphodiesterase IV-Inhibitoren |
| US20040259863A1 (en) * | 2001-10-31 | 2004-12-23 | Hans-Michael Eggenweiler | Type 4 phosphodiesterase inhibitors and uses thereof |
| ES2195785B1 (es) * | 2002-05-16 | 2005-03-16 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| US7074959B2 (en) * | 2002-08-01 | 2006-07-11 | New Mexico Highlands University | Methods and systems for remediating hydrazine-contaminated equipment and/or surfaces |
| ES2211344B1 (es) * | 2002-12-26 | 2005-10-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| EP1624893A2 (en) | 2003-04-01 | 2006-02-15 | Applied Research Systems ARS Holding N.V. | Inhibitors of phosphodiesterases in infertility |
| WO2005075437A1 (en) * | 2004-02-04 | 2005-08-18 | Altana Pharma Ag | Pyridazinone derivatives and their use as pde4 inhibitors |
| ES2304692T3 (es) * | 2004-02-04 | 2008-10-16 | Nycomed Gmbh | Derivados de 2-(piperidin-4-il)-4,5-dihidro-2h-piridazin-3-ona como inhibidores de pde4. |
| ES2251867B1 (es) * | 2004-06-21 | 2007-06-16 | Laboratorios Almirall S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| MX2009006312A (es) * | 2006-12-14 | 2009-08-07 | Astellas Pharma Inc | Compuestos de acido policiclico utiles como antagonistas crth2 y agentes antialergicos. |
| US8466198B2 (en) * | 2008-09-02 | 2013-06-18 | Bruce Kneller | Compositions comprising creatine salts and methods of use thereof |
| EP2298090B1 (en) * | 2009-08-26 | 2016-01-13 | Jeffrey M. Golini | Pharmaceutical or nutraceutical composition |
| KR102520814B1 (ko) | 2016-03-16 | 2023-04-11 | 에이치 리 모피트 캔서 센터 앤드 리서어치 인스티튜트 아이엔씨 | 작동자 t 세포 기능 개선을 위한 세레브론에 대한 소분자 |
| WO2020014489A2 (en) | 2018-07-11 | 2020-01-16 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Dimeric immuno-modulatory compounds against cereblon-based mechanisms |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1604863A (cs) * | 1967-11-22 | 1972-04-17 | ||
| US3975388A (en) * | 1971-02-22 | 1976-08-17 | Bdh Pharmaceuticals Limited | Pyridazinones |
| GB1488330A (en) * | 1973-12-19 | 1977-10-12 | Smith Kline French Lab | Dihydropyridazinones |
| DE2845456A1 (de) | 1978-10-19 | 1980-08-14 | Merck Patent Gmbh | 6-arylpyridazin-3-one und verfahren zu ihrer herstellung |
| US4397854A (en) * | 1981-05-14 | 1983-08-09 | Warner-Lambert Company | Substituted 6-phenyl-3(2H)-pyridazinones useful as cardiotonic agents |
| SU1313346A3 (ru) * | 1981-09-17 | 1987-05-23 | Варнер-Ламберт,Компани (Фирма) | Способ получени замещенных 6-арил-3(2 @ )-пиридазинонов |
| US4734415A (en) * | 1982-08-13 | 1988-03-29 | Warner-Lambert Company | Substituted 4,5-dihydro-6-(substituted)-phenyl-3(2H)-pyridazinones and 6-(substituted) phenyl-3(2H)-pyridazinones |
| GR82072B (cs) * | 1983-05-11 | 1984-12-13 | Byk Gulden Lomberg Chem Fab | |
| US4666902A (en) * | 1983-06-20 | 1987-05-19 | Cassella Aktiengesellschaft | Tetrahydropyridazinone derivatives, processes for their preparation and their use |
| US4816454A (en) * | 1984-09-21 | 1989-03-28 | Cassella Aktiengesellschaft | 4,5-dihydro-3(2H)-pyridazinones and their pharmacological use |
| JPS61158969A (ja) * | 1984-12-24 | 1986-07-18 | ワーナー‐ランバート・コンパニー | ４，５‐ジヒドロ‐４，４‐ジアルキル‐６‐（置換）フエニル‐３（２ｈ）‐ピリダジノン類 |
| DE3704879A1 (de) * | 1987-02-17 | 1988-08-25 | Merck Patent Gmbh | Pyridazinonderivate |
| GB8903130D0 (en) | 1989-02-11 | 1989-03-30 | Orion Yhtymae Oy | Substituted pyridazinones |
| US5175161A (en) * | 1989-04-06 | 1992-12-29 | Sankyo Company, Limited | Occular hypotensive agents |
| KR910004574A (ko) * | 1989-08-10 | 1991-03-28 | 글락소 인크 | 강심 작용 및 베타 차단 작용을 갖는 피리다지논류 |
| DE4237656A1 (de) * | 1992-06-13 | 1993-12-16 | Merck Patent Gmbh | Benzimidazolderivate |
| JP2806192B2 (ja) * | 1992-11-02 | 1998-09-30 | 日本曹達株式会社 | 血小板凝集抑制剤 |
| DE19502699A1 (de) | 1995-01-28 | 1996-08-01 | Merck Patent Gmbh | Arylalkyl-thiadiazinone |
-
1995
- 1995-04-20 DE DE19514568A patent/DE19514568A1/de not_active Withdrawn
-
1996
- 1996-02-27 TW TW085102257A patent/TW475927B/zh not_active IP Right Cessation
- 1996-04-11 PT PT96105702T patent/PT738715E/pt unknown
- 1996-04-11 AT AT96105702T patent/ATE231842T1/de active
- 1996-04-11 DK DK96105702T patent/DK0738715T3/da active
- 1996-04-11 EP EP96105702A patent/EP0738715B1/de not_active Expired - Lifetime
- 1996-04-11 ES ES96105702T patent/ES2191070T3/es not_active Expired - Lifetime
- 1996-04-11 DE DE59610081T patent/DE59610081D1/de not_active Expired - Lifetime
- 1996-04-11 SI SI9630593T patent/SI0738715T1/xx unknown
- 1996-04-16 AU AU50711/96A patent/AU705025B2/en not_active Ceased
- 1996-04-17 SK SK487-96A patent/SK284167B6/sk unknown
- 1996-04-18 CA CA002174472A patent/CA2174472C/en not_active Expired - Fee Related
- 1996-04-18 CN CNB961051086A patent/CN1159299C/zh not_active Expired - Fee Related
- 1996-04-19 JP JP12078096A patent/JP4005157B2/ja not_active Expired - Fee Related
- 1996-04-19 CZ CZ19961132A patent/CZ291868B6/cs not_active IP Right Cessation
- 1996-04-19 HU HU9601034A patent/HU226198B1/hu not_active IP Right Cessation
- 1996-04-19 KR KR1019960011859A patent/KR100428879B1/ko not_active Expired - Fee Related
- 1996-04-19 US US08/634,830 patent/US6399611B1/en not_active Expired - Fee Related
- 1996-04-19 NO NO961578A patent/NO307931B1/no not_active IP Right Cessation
- 1996-04-19 RU RU96107677/04A patent/RU2159236C2/ru not_active IP Right Cessation
- 1996-04-19 ZA ZA963154A patent/ZA963154B/xx unknown
- 1996-04-19 UA UA96041565A patent/UA43853C2/uk unknown
-
2002
- 2002-04-08 US US10/117,217 patent/US6531473B2/en not_active Expired - Fee Related
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