DE2834624A1 - Neue 1,4-dihydropyridazin-3-carbonsaeurederivate, verfahren zu ihrer herstellung und verwendung als arzneimittel - Google Patents
Neue 1,4-dihydropyridazin-3-carbonsaeurederivate, verfahren zu ihrer herstellung und verwendung als arzneimittelInfo
- Publication number
- DE2834624A1 DE2834624A1 DE19782834624 DE2834624A DE2834624A1 DE 2834624 A1 DE2834624 A1 DE 2834624A1 DE 19782834624 DE19782834624 DE 19782834624 DE 2834624 A DE2834624 A DE 2834624A DE 2834624 A1 DE2834624 A1 DE 2834624A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- alkyl
- radical
- optionally
- stands
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 title abstract description 8
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- -1 Alkyl radical Chemical class 0.000 claims description 129
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052736 halogen Chemical group 0.000 claims description 27
- 150000002367 halogens Chemical group 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- 125000001544 thienyl group Chemical group 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000002541 furyl group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 12
- 150000002431 hydrogen Chemical group 0.000 claims description 11
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 150000005840 aryl radicals Chemical class 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 150000002429 hydrazines Chemical class 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 238000007127 saponification reaction Methods 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 230000009435 amidation Effects 0.000 claims description 4
- 238000007112 amidation reaction Methods 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 230000032050 esterification Effects 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 238000005809 transesterification reaction Methods 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- 210000002460 smooth muscle Anatomy 0.000 claims description 3
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 206010061218 Inflammation Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 7
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 6
- VVFXLJCJOPOIFO-UHFFFAOYSA-N 1,4-dihydropyridazine-3-carboxylic acid Chemical class OC(=O)C1=NNC=CC1 VVFXLJCJOPOIFO-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000812 cholinergic antagonist Substances 0.000 abstract description 4
- 230000002048 spasmolytic effect Effects 0.000 abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 57
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 159000000000 sodium salts Chemical class 0.000 description 36
- 238000002844 melting Methods 0.000 description 30
- 230000008018 melting Effects 0.000 description 30
- 150000002148 esters Chemical class 0.000 description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
- 235000019441 ethanol Nutrition 0.000 description 24
- 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 19
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
- 238000010898 silica gel chromatography Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 6
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 5
- HZVGMPJZVYBYEK-UHFFFAOYSA-N 1,4-dihydropyridazine Chemical class C1C=CNN=C1 HZVGMPJZVYBYEK-UHFFFAOYSA-N 0.000 description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 4
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- NTCNSIFTFKBJIN-UHFFFAOYSA-N 1,4-dihydropyridazine-3,5-dicarboxylic acid Chemical class OC(=O)C1=CNN=C(C(O)=O)C1 NTCNSIFTFKBJIN-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- CXNUYNNVHHAWPN-UHFFFAOYSA-N 4-carboxy-n,1-dihydroxy-3-(3-nitrophenyl)-1,5-dioxohexan-2-imine oxide Chemical compound CC(=O)C(C(O)=O)C(\C(C(O)=O)=[N+](/O)[O-])C1=CC=CC([N+]([O-])=O)=C1 CXNUYNNVHHAWPN-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- MDKLAOSKCVGSQH-UHFFFAOYSA-N diethyl 6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridazine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=NNC(C)=C(C(=O)OCC)C1C1=CC=CC([N+]([O-])=O)=C1 MDKLAOSKCVGSQH-UHFFFAOYSA-N 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
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- 229910052623 talc Inorganic materials 0.000 description 3
- 230000002792 vascular Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YXSNCCXAJNWTSO-UHFFFAOYSA-N 4-(3-chlorophenyl)-5-ethoxycarbonyl-6-methyl-1,4-dihydropyridazine-3-carboxylic acid Chemical compound CCOC(=O)C1=C(C)NN=C(C(O)=O)C1C1=CC=CC(Cl)=C1 YXSNCCXAJNWTSO-UHFFFAOYSA-N 0.000 description 2
- RYMXOSNDOSCBNY-UHFFFAOYSA-N 4-(3-chlorophenyl)-6-methyl-1,4-dihydropyridazine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=NNC(C)=C(C(O)=O)C1C1=CC=CC(Cl)=C1 RYMXOSNDOSCBNY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
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- 210000002345 respiratory system Anatomy 0.000 description 2
- 239000011435 rock Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000015424 sodium Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
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- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 1
- BKWQKVJYXODDAC-UHFFFAOYSA-N 1,2-dihydropyridazine Chemical compound N1NC=CC=C1 BKWQKVJYXODDAC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RNHZERMQWQTWSD-UHFFFAOYSA-N 1-cyclopentyloxy-n-hydroxy-1,5-dioxo-3-[2-(trifluoromethyl)phenyl]heptan-2-imine oxide Chemical compound C=1C=CC=C(C(F)(F)F)C=1C(CC(=O)CC)C(=[N+](O)[O-])C(=O)OC1CCCC1 RNHZERMQWQTWSD-UHFFFAOYSA-N 0.000 description 1
- PLWIJOQNBZESAZ-UHFFFAOYSA-N 1-ethoxy-4-ethoxycarbonyl-n-hydroxy-1,5-dioxo-3-(1h-pyrrol-2-yl)hexan-2-imine oxide Chemical compound CCOC(=O)C(C(C)=O)C(C(C(=O)OCC)=[N+](O)[O-])C1=CC=CN1 PLWIJOQNBZESAZ-UHFFFAOYSA-N 0.000 description 1
- BARMLROCTIMJIE-UHFFFAOYSA-N 1-ethoxy-4-ethoxycarbonyl-n-hydroxy-3-(2-nitrophenyl)-1,5-dioxohexan-2-imine oxide Chemical compound CCOC(=O)C(C(C)=O)C(C(C(=O)OCC)=[N+](O)[O-])C1=CC=CC=C1[N+]([O-])=O BARMLROCTIMJIE-UHFFFAOYSA-N 0.000 description 1
- OBOLDSBNWXMFJU-UHFFFAOYSA-N 1-ethoxy-4-ethoxycarbonyl-n-hydroxy-3-(3-nitrophenyl)-1,5-dioxohexan-2-imine oxide Chemical compound CCOC(=O)C(C(C)=O)C(C(C(=O)OCC)=[N+](O)[O-])C1=CC=CC([N+]([O-])=O)=C1 OBOLDSBNWXMFJU-UHFFFAOYSA-N 0.000 description 1
- LNXWPJTXAJRWHG-UHFFFAOYSA-N 1-ethoxy-n-hydroxy-3-(3-nitrophenyl)-1,5-dioxohexan-2-imine oxide Chemical compound CCOC(=O)C(=[N+](O)[O-])C(CC(C)=O)C1=CC=CC([N+]([O-])=O)=C1 LNXWPJTXAJRWHG-UHFFFAOYSA-N 0.000 description 1
- MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical group CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 description 1
- IBELBRDFPCFICX-UHFFFAOYSA-N 2-methoxyethylhydrazine Chemical compound COCCNN IBELBRDFPCFICX-UHFFFAOYSA-N 0.000 description 1
- NGSOWKPBNFOQCR-UHFFFAOYSA-N 2-methylpropylhydrazine Chemical compound CC(C)CNN NGSOWKPBNFOQCR-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- CASHMQRDJKEXTO-UHFFFAOYSA-N 3-(2-chloro-5-nitrophenyl)-n-hydroxy-1-methoxy-4-methoxycarbonyl-1,5-dioxohexan-2-imine oxide Chemical compound COC(=O)C(C(C)=O)C(C(C(=O)OC)=[N+](O)[O-])C1=CC([N+]([O-])=O)=CC=C1Cl CASHMQRDJKEXTO-UHFFFAOYSA-N 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- UDWXLZLRRVQONG-UHFFFAOYSA-M sodium hexanoate Chemical compound [Na+].CCCCCC([O-])=O UDWXLZLRRVQONG-UHFFFAOYSA-M 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 125000005853 β-dimethylaminoethyl group Chemical group 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (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)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782834624 DE2834624A1 (de) | 1978-08-08 | 1978-08-08 | Neue 1,4-dihydropyridazin-3-carbonsaeurederivate, verfahren zu ihrer herstellung und verwendung als arzneimittel |
| US06/058,590 US4280998A (en) | 1978-08-08 | 1979-07-18 | 1,4-Dihydropyridazine-3-carboxylic acid derivatives, a process for their preparation and their use as antihypertensives |
| EP79102712A EP0009560B1 (de) | 1978-08-08 | 1979-07-30 | Neue 1,4-Dihydropyridazin-3-carbonylverbindungen, Verfahren zu ihrer Herstellung, die Verbindungen zur Verwendung bei der Behandlung von Krankheiten, diese enthaltende Arzneimittel und Verfahren zur Herstellung der Arzneimittel |
| AT79102712T ATE1583T1 (de) | 1978-08-08 | 1979-07-30 | Neue 1,4-dihydropyridazin-3-carbonylverbindungen, verfahren zu ihrer herstellung, die verbindungen zur verwendung bei der behandlung von krankheiten, diese enthaltende arzneimittel und verfahren zur herstellung der arzneimittel. |
| DE7979102712T DE2963730D1 (en) | 1978-08-08 | 1979-07-30 | 1,4-dihydropyridazine-3-carbonyl compounds, process for their preparation, the compounds for use in curing diseases, medicaments containing them and process for the preparation of the medicaments |
| JP9952479A JPS5536484A (en) | 1978-08-08 | 1979-08-06 | Novel 1*44dihydropyridazinee33carboxylic acid derivative |
| ES483201A ES483201A1 (es) | 1978-08-08 | 1979-08-07 | Procedimiento para la obtencion de derivados de acido 1,4- dihidropiridazin-3-carboxilico |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782834624 DE2834624A1 (de) | 1978-08-08 | 1978-08-08 | Neue 1,4-dihydropyridazin-3-carbonsaeurederivate, verfahren zu ihrer herstellung und verwendung als arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2834624A1 true DE2834624A1 (de) | 1980-02-28 |
Family
ID=6046444
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782834624 Withdrawn DE2834624A1 (de) | 1978-08-08 | 1978-08-08 | Neue 1,4-dihydropyridazin-3-carbonsaeurederivate, verfahren zu ihrer herstellung und verwendung als arzneimittel |
| DE7979102712T Expired DE2963730D1 (en) | 1978-08-08 | 1979-07-30 | 1,4-dihydropyridazine-3-carbonyl compounds, process for their preparation, the compounds for use in curing diseases, medicaments containing them and process for the preparation of the medicaments |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE7979102712T Expired DE2963730D1 (en) | 1978-08-08 | 1979-07-30 | 1,4-dihydropyridazine-3-carbonyl compounds, process for their preparation, the compounds for use in curing diseases, medicaments containing them and process for the preparation of the medicaments |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4280998A (en, 2012) |
| EP (1) | EP0009560B1 (en, 2012) |
| JP (1) | JPS5536484A (en, 2012) |
| AT (1) | ATE1583T1 (en, 2012) |
| DE (2) | DE2834624A1 (en, 2012) |
| ES (1) | ES483201A1 (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1983000863A1 (en) * | 1981-09-11 | 1983-03-17 | Diamond Shamrock Corp | Antiinflammatory and analgetic 4-pyridylpyridazin(2h)-3-ones |
| FR2515652B1 (fr) * | 1981-11-03 | 1985-10-25 | Sandoz Sa | Nouveaux derives de la 1,4-dihydropyridazine, leur preparation et medicaments contenant ces derives |
| DE3431700A1 (de) * | 1984-08-29 | 1986-03-13 | Bayer Ag, 5090 Leverkusen | Neue 1,4-dihydro-pyridazin-derivate, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| GB8530602D0 (en) * | 1985-12-12 | 1986-01-22 | Fujisawa Pharmaceutical Co | Heterocyclic compounds |
| JPH0258603U (en, 2012) * | 1988-10-18 | 1990-04-26 |
-
1978
- 1978-08-08 DE DE19782834624 patent/DE2834624A1/de not_active Withdrawn
-
1979
- 1979-07-18 US US06/058,590 patent/US4280998A/en not_active Expired - Lifetime
- 1979-07-30 AT AT79102712T patent/ATE1583T1/de not_active IP Right Cessation
- 1979-07-30 DE DE7979102712T patent/DE2963730D1/de not_active Expired
- 1979-07-30 EP EP79102712A patent/EP0009560B1/de not_active Expired
- 1979-08-06 JP JP9952479A patent/JPS5536484A/ja active Granted
- 1979-08-07 ES ES483201A patent/ES483201A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0009560A1 (de) | 1980-04-16 |
| ATE1583T1 (de) | 1982-10-15 |
| US4280998A (en) | 1981-07-28 |
| DE2963730D1 (en) | 1982-11-04 |
| JPS5536484A (en) | 1980-03-14 |
| ES483201A1 (es) | 1980-05-16 |
| EP0009560B1 (de) | 1982-09-22 |
| JPS6317068B2 (en, 2012) | 1988-04-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |