JPS6225661B2 - - Google Patents
Info
- Publication number
- JPS6225661B2 JPS6225661B2 JP53111390A JP11139078A JPS6225661B2 JP S6225661 B2 JPS6225661 B2 JP S6225661B2 JP 53111390 A JP53111390 A JP 53111390A JP 11139078 A JP11139078 A JP 11139078A JP S6225661 B2 JPS6225661 B2 JP S6225661B2
- Authority
- JP
- Japan
- Prior art keywords
- ester
- dihydro
- pyridazine
- oxo
- acetyl
- 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.)
- Expired
Links
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 95
- -1 1,4-dihydropyridazine compound Chemical class 0.000 claims description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 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 claims description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 63
- 238000002844 melting Methods 0.000 description 36
- 230000008018 melting Effects 0.000 description 36
- 150000001875 compounds Chemical class 0.000 description 28
- 239000003814 drug Substances 0.000 description 23
- 239000003085 diluting agent Substances 0.000 description 21
- 229940079593 drug Drugs 0.000 description 16
- 239000000203 mixture Substances 0.000 description 13
- 239000000825 pharmaceutical preparation Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 239000008298 dragée Substances 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000006187 pill Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- HZVGMPJZVYBYEK-UHFFFAOYSA-N 1,4-dihydropyridazine Chemical class C1C=CNN=C1 HZVGMPJZVYBYEK-UHFFFAOYSA-N 0.000 description 3
- ZWVRKXFAQNZERD-UHFFFAOYSA-N 3-ethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridazine-5-carboxylic acid Chemical compound CCC1=NNC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 ZWVRKXFAQNZERD-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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000002921 anti-spasmodic effect Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- DKBFZSSBVYKEAF-UHFFFAOYSA-N ethyl 6-methylpyridazine-4-carboxylate Chemical compound CCOC(=O)C1=CN=NC(C)=C1 DKBFZSSBVYKEAF-UHFFFAOYSA-N 0.000 description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 235000010419 agar Nutrition 0.000 description 2
- 235000012216 bentonite Nutrition 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000002934 diuretic Substances 0.000 description 2
- HXSTXSIIJLVVTI-UHFFFAOYSA-N ethyl 2-acetyl-3-(3-nitrophenyl)-4-oxohexanoate Chemical compound CCOC(=O)C(C(C)=O)C(C(=O)CC)C1=CC=CC([N+]([O-])=O)=C1 HXSTXSIIJLVVTI-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000000865 liniment Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- YLYUZNISKXJBHU-UHFFFAOYSA-N methyl 2-acetyl-4-oxo-3,4-diphenylbutanoate Chemical compound C=1C=CC=CC=1C(C(C(=O)OC)C(C)=O)C(=O)C1=CC=CC=C1 YLYUZNISKXJBHU-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 210000002345 respiratory system Anatomy 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000007493 shaping process Methods 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 235000010487 tragacanth Nutrition 0.000 description 2
- 229940116362 tragacanth Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- BKWQKVJYXODDAC-UHFFFAOYSA-N 1,2-dihydropyridazine Chemical compound N1NC=CC=C1 BKWQKVJYXODDAC-UHFFFAOYSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SKYWPEOJFSQKOB-UHFFFAOYSA-N 1-[3-butyl-4-(3-methylsulfanylphenyl)-1,4-dihydropyridazin-5-yl]ethanone Chemical compound CCCCC1=NNC=C(C(C)=O)C1C1=CC=CC(SC)=C1 SKYWPEOJFSQKOB-UHFFFAOYSA-N 0.000 description 1
- OYEWMWQJKIURFP-UHFFFAOYSA-N 1-[4-(3-chlorophenyl)-3-ethyl-6-methyl-1,4-dihydropyridazin-5-yl]ethanone Chemical compound CCC1=NNC(C)=C(C(C)=O)C1C1=CC=CC(Cl)=C1 OYEWMWQJKIURFP-UHFFFAOYSA-N 0.000 description 1
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical class CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 1
- WCADNWYWINILQG-UHFFFAOYSA-N 2-(5-benzoyl-3-ethyl-6-methyl-1,4-dihydropyridazin-4-yl)benzonitrile Chemical compound CCC1=NNC(C)=C(C(=O)C=2C=CC=CC=2)C1C1=CC=CC=C1C#N WCADNWYWINILQG-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- RTBBACMUAYAWDW-UHFFFAOYSA-N 2-[1-(3,4-dichlorophenyl)-2-oxobutyl]cyclohexane-1,3-dione Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C(=O)CC)C1C(=O)CCCC1=O RTBBACMUAYAWDW-UHFFFAOYSA-N 0.000 description 1
- SPVUPXWCBVWEAD-UHFFFAOYSA-N 2-acetyl-3-(3-nitrophenyl)-4-oxohexanehydrazide Chemical compound NNC(=O)C(C(C)=O)C(C(=O)CC)C1=CC=CC([N+]([O-])=O)=C1 SPVUPXWCBVWEAD-UHFFFAOYSA-N 0.000 description 1
- OKGXLUUNABOIMT-UHFFFAOYSA-N 2-methylpropyl 2-acetyl-3-(2-nitrophenyl)-4-oxohexanoate Chemical compound CC(C)COC(=O)C(C(C)=O)C(C(=O)CC)C1=CC=CC=C1[N+]([O-])=O OKGXLUUNABOIMT-UHFFFAOYSA-N 0.000 description 1
- VPTLARAIYOGFDX-UHFFFAOYSA-N 3-acetyl-4-(3-nitrophenyl)heptane-2,5-dione Chemical compound CCC(=O)C(C(C(C)=O)C(C)=O)C1=CC=CC([N+]([O-])=O)=C1 VPTLARAIYOGFDX-UHFFFAOYSA-N 0.000 description 1
- NTJFXCVYLXZRHC-UHFFFAOYSA-N 3-acetyl-5-oxo-4-phenylundecanehydrazide Chemical compound CCCCCCC(=O)C(C(CC(=O)NN)C(C)=O)C1=CC=CC=C1 NTJFXCVYLXZRHC-UHFFFAOYSA-N 0.000 description 1
- XVMSHQYSKIYWRG-UHFFFAOYSA-N 3-benzoyl-4-[4-(trifluoromethyl)phenyl]heptane-2,5-dione Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(C(=O)CC)C(C(C)=O)C(=O)C1=CC=CC=C1 XVMSHQYSKIYWRG-UHFFFAOYSA-N 0.000 description 1
- MZCJUBWHRYFLKA-UHFFFAOYSA-N 3-ethyl-4-(3-nitrophenyl)-4,7-dihydro-1h-furo[3,4-c]pyridazin-5-one Chemical compound CCC1=NNC(COC2=O)=C2C1C1=CC=CC([N+]([O-])=O)=C1 MZCJUBWHRYFLKA-UHFFFAOYSA-N 0.000 description 1
- HQOWXMZUYJVOJO-UHFFFAOYSA-N C(CC)OC(C(C(C(C)=O)C1=C(C(=CC=C1)C)S)C(C)=O)=O Chemical compound C(CC)OC(C(C(C(C)=O)C1=C(C(=CC=C1)C)S)C(C)=O)=O HQOWXMZUYJVOJO-UHFFFAOYSA-N 0.000 description 1
- UIPCCSOKBDSRBC-UHFFFAOYSA-N CCOC(=O)C1=C(C)NN=C(C(F)(F)C(F)(F)F)C1C1=CC=CC([N+]([O-])=O)=C1 Chemical compound CCOC(=O)C1=C(C)NN=C(C(F)(F)C(F)(F)F)C1C1=CC=CC([N+]([O-])=O)=C1 UIPCCSOKBDSRBC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 239000005973 Carvone Substances 0.000 description 1
- 235000017788 Cydonia oblonga Nutrition 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 244000166124 Eucalyptus globulus Species 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 238000006987 Nef reaction Methods 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 230000003440 anti-fibrillation Effects 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 229940124575 antispasmodic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 229940097320 beta blocking agent Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000012241 calcium silicate Nutrition 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 206010007776 catatonia Diseases 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 150000005827 chlorofluoro hydrocarbons Chemical class 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- KUHUOMASZUDHKK-UHFFFAOYSA-N cyclohexyl 2-acetyl-3-(3-methylphenyl)-4-oxohexanoate Chemical compound C=1C=CC(C)=CC=1C(C(=O)CC)C(C(C)=O)C(=O)OC1CCCCC1 KUHUOMASZUDHKK-UHFFFAOYSA-N 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- DEYWCGIULYUSMB-UHFFFAOYSA-N ethyl 2-acetyl-3-(2-cyanophenyl)-4-oxononanoate Chemical compound CCCCCC(=O)C(C(C(C)=O)C(=O)OCC)C1=CC=CC=C1C#N DEYWCGIULYUSMB-UHFFFAOYSA-N 0.000 description 1
- UZCBBWOQUJDKIL-UHFFFAOYSA-N ethyl 2-acetyl-3-(2-nitrophenyl)-4-oxoheptanoate Chemical compound CCOC(=O)C(C(C)=O)C(C(=O)CCC)C1=CC=CC=C1[N+]([O-])=O UZCBBWOQUJDKIL-UHFFFAOYSA-N 0.000 description 1
- CVVWURBUBPQQAQ-UHFFFAOYSA-N ethyl 2-acetyl-3-(2-nitrophenyl)-4-oxohexanoate Chemical compound CCOC(=O)C(C(C)=O)C(C(=O)CC)C1=CC=CC=C1[N+]([O-])=O CVVWURBUBPQQAQ-UHFFFAOYSA-N 0.000 description 1
- RENCOQWWFGCOSA-UHFFFAOYSA-N ethyl 2-acetyl-4-oxo-3,4-diphenylbutanoate Chemical compound C=1C=CC=CC=1C(C(C(=O)OCC)C(C)=O)C(=O)C1=CC=CC=C1 RENCOQWWFGCOSA-UHFFFAOYSA-N 0.000 description 1
- XJBJULZWTWWDOI-UHFFFAOYSA-N ethyl 2-acetyl-4-oxo-3-phenylhexanoate Chemical compound CCOC(=O)C(C(C)=O)C(C(=O)CC)C1=CC=CC=C1 XJBJULZWTWWDOI-UHFFFAOYSA-N 0.000 description 1
- OIPDNKFVJQPXHU-UHFFFAOYSA-N ethyl 2-acetyl-4-oxo-3-phenylpentanoate Chemical compound CCOC(=O)C(C(C)=O)C(C(C)=O)C1=CC=CC=C1 OIPDNKFVJQPXHU-UHFFFAOYSA-N 0.000 description 1
- NIHYSSPYGQHDCE-UHFFFAOYSA-N ethyl 3,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridazine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)NN=C(C)C1C1=CC=CC([N+]([O-])=O)=C1 NIHYSSPYGQHDCE-UHFFFAOYSA-N 0.000 description 1
- KGDVIPAGJSVSJF-UHFFFAOYSA-N ethyl 3,6-dimethyl-4-phenyl-1,4-dihydropyridazine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)NN=C(C)C1C1=CC=CC=C1 KGDVIPAGJSVSJF-UHFFFAOYSA-N 0.000 description 1
- TWEPKQNPFRQGIU-UHFFFAOYSA-N ethyl 3-(2-butoxyethyl)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridazine-5-carboxylate Chemical compound CCCCOCCC1=NNC(C)=C(C(=O)OCC)C1C1=CC=CC([N+]([O-])=O)=C1 TWEPKQNPFRQGIU-UHFFFAOYSA-N 0.000 description 1
- SUKUCBQBBCIFEV-UHFFFAOYSA-N ethyl 3-(3-chlorophenyl)-4-oxo-2-propanoylpentanoate Chemical compound CCOC(=O)C(C(=O)CC)C(C(C)=O)C1=CC=CC(Cl)=C1 SUKUCBQBBCIFEV-UHFFFAOYSA-N 0.000 description 1
- LEORWWQIRIDHAG-UHFFFAOYSA-N ethyl 3-ethyl-4-(4-methoxyphenyl)-6-methyl-1,4-dihydropyridazine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)NN=C(CC)C1C1=CC=C(OC)C=C1 LEORWWQIRIDHAG-UHFFFAOYSA-N 0.000 description 1
- PAIBAIIQHCQEKY-UHFFFAOYSA-N ethyl 3-ethyl-6-methyl-4-(3-methylsulfonylphenyl)-1,4-dihydropyridazine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)NN=C(CC)C1C1=CC=CC(S(C)(=O)=O)=C1 PAIBAIIQHCQEKY-UHFFFAOYSA-N 0.000 description 1
- VTRLRJORLLQMCY-UHFFFAOYSA-N ethyl 3-ethyl-6-methyl-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridazine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)NN=C(CC)C1C1=CC=CC=C1C(F)(F)F VTRLRJORLLQMCY-UHFFFAOYSA-N 0.000 description 1
- XQRHXLRVQLEIEC-UHFFFAOYSA-N ethyl 3-ethyl-6-methyl-4-phenyl-1,4-dihydropyridazine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)NN=C(CC)C1C1=CC=CC=C1 XQRHXLRVQLEIEC-UHFFFAOYSA-N 0.000 description 1
- SNNBONWEPDNVHX-UHFFFAOYSA-N ethyl 4-(2-cyanophenyl)-3,6-dimethyl-1,4-dihydropyridazine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)NN=C(C)C1C1=CC=CC=C1C#N SNNBONWEPDNVHX-UHFFFAOYSA-N 0.000 description 1
- QDZRDQDJIFINAT-UHFFFAOYSA-N ethyl 4-(3-chlorophenyl)-3-hexyl-6-methyl-1,4-dihydropyridazine-5-carboxylate Chemical compound CCCCCCC1=NNC(C)=C(C(=O)OCC)C1C1=CC=CC(Cl)=C1 QDZRDQDJIFINAT-UHFFFAOYSA-N 0.000 description 1
- PQKGUECTOZFPSE-UHFFFAOYSA-N ethyl 4-oxohexanoate Chemical compound CCOC(=O)CCC(=O)CC PQKGUECTOZFPSE-UHFFFAOYSA-N 0.000 description 1
- YPTVYPIYVLYKEH-UHFFFAOYSA-N ethyl 6-(acetyloxymethyl)-3-ethyl-4-(3-nitrophenyl)-1,4-dihydropyridazine-5-carboxylate Chemical compound CCOC(=O)C1=C(COC(C)=O)NN=C(CC)C1C1=CC=CC([N+]([O-])=O)=C1 YPTVYPIYVLYKEH-UHFFFAOYSA-N 0.000 description 1
- QOTLNILUKMPMII-UHFFFAOYSA-N ethyl 6-methyl-3,4-diphenyl-1,4-dihydropyridazine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)NN=C(C=2C=CC=CC=2)C1C1=CC=CC=C1 QOTLNILUKMPMII-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 230000002964 excitative effect Effects 0.000 description 1
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- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 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
- XLYJABYWXDTQGH-UHFFFAOYSA-N hexyl 2-acetyl-3-(2-cyanophenyl)-4-oxohexanoate Chemical compound CCCCCCOC(=O)C(C(C)=O)C(C(=O)CC)C1=CC=CC=C1C#N XLYJABYWXDTQGH-UHFFFAOYSA-N 0.000 description 1
- VWRIGCKROFHTGW-UHFFFAOYSA-N hexyl 2-acetyl-3-(3-chlorophenyl)-4-oxo-4-phenylbutanoate Chemical compound C=1C=CC(Cl)=CC=1C(C(C(=O)OCCCCCC)C(C)=O)C(=O)C1=CC=CC=C1 VWRIGCKROFHTGW-UHFFFAOYSA-N 0.000 description 1
- UBCVCYJORGMROB-UHFFFAOYSA-N hexyl 3-ethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridazine-5-carboxylate Chemical compound CCCCCCOC(=O)C1=C(C)NN=C(CC)C1C1=CC=CC([N+]([O-])=O)=C1 UBCVCYJORGMROB-UHFFFAOYSA-N 0.000 description 1
- DDQLUDURUSYIRD-UHFFFAOYSA-N hexyl 4-(3-chlorophenyl)-6-methyl-3-phenyl-1,4-dihydropyridazine-5-carboxylate Chemical compound CCCCCCOC(=O)C1=C(C)NN=C(C=2C=CC=CC=2)C1C1=CC=CC(Cl)=C1 DDQLUDURUSYIRD-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
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- PMDCWPSWNAHCKC-UHFFFAOYSA-N methyl 2-acetyl-3-(2-chlorophenyl)-4-oxo-4-phenylbutanoate Chemical compound C=1C=CC=C(Cl)C=1C(C(C(=O)OC)C(C)=O)C(=O)C1=CC=CC=C1 PMDCWPSWNAHCKC-UHFFFAOYSA-N 0.000 description 1
- TYXMXDMPAKVALA-UHFFFAOYSA-N methyl 2-acetyl-3-(3,4-dichlorophenyl)-4-oxohexanoate Chemical compound COC(=O)C(C(C)=O)C(C(=O)CC)C1=CC=C(Cl)C(Cl)=C1 TYXMXDMPAKVALA-UHFFFAOYSA-N 0.000 description 1
- VULWFVSQFSDFRX-UHFFFAOYSA-N methyl 2-acetyl-3-(3-chlorophenyl)-6-methylsulfanyl-4-oxohexanoate Chemical compound CSCCC(=O)C(C(C(=O)OC)C(C)=O)C1=CC=CC(Cl)=C1 VULWFVSQFSDFRX-UHFFFAOYSA-N 0.000 description 1
- PGHSNWXEVOITCL-UHFFFAOYSA-N methyl 2-acetyl-3-(3-nitrophenyl)-4-oxo-6-phenylhexanoate Chemical compound C=1C=CC([N+]([O-])=O)=CC=1C(C(C(=O)OC)C(C)=O)C(=O)CCC1=CC=CC=C1 PGHSNWXEVOITCL-UHFFFAOYSA-N 0.000 description 1
- AYHBKYNMWUXLLI-UHFFFAOYSA-N methyl 2-acetyl-3-(3-nitrophenyl)-4-oxohexanoate Chemical compound COC(=O)C(C(C)=O)C(C(=O)CC)C1=CC=CC([N+]([O-])=O)=C1 AYHBKYNMWUXLLI-UHFFFAOYSA-N 0.000 description 1
- SGBWBOYYIYBPNR-UHFFFAOYSA-N methyl 2-acetyl-3-(4-methylsulfonylphenyl)-4-oxohexanoate Chemical compound COC(=O)C(C(C)=O)C(C(=O)CC)C1=CC=C(S(C)(=O)=O)C=C1 SGBWBOYYIYBPNR-UHFFFAOYSA-N 0.000 description 1
- YRZXXWBAZHPWIY-UHFFFAOYSA-N methyl 2-acetyl-4-(4,4-dimethyl-5h-1,3-oxazol-2-yl)-4-oxo-3-[2-(trifluoromethyl)phenyl]butanoate Chemical compound C=1C=CC=C(C(F)(F)F)C=1C(C(C(=O)OC)C(C)=O)C(=O)C1=NC(C)(C)CO1 YRZXXWBAZHPWIY-UHFFFAOYSA-N 0.000 description 1
- ZSDULTXCKSCHDF-UHFFFAOYSA-N methyl 2-acetyl-4-cyclohexyl-3-(2-nitrophenyl)-4-oxobutanoate Chemical compound C=1C=CC=C([N+]([O-])=O)C=1C(C(C(=O)OC)C(C)=O)C(=O)C1CCCCC1 ZSDULTXCKSCHDF-UHFFFAOYSA-N 0.000 description 1
- MRDAIUDLPDNALE-UHFFFAOYSA-N methyl 2-acetyl-4-oxo-3-[4-(trifluoromethoxy)phenyl]butanoate Chemical compound COC(=O)C(C(C)=O)C(C=O)C1=CC=C(OC(F)(F)F)C=C1 MRDAIUDLPDNALE-UHFFFAOYSA-N 0.000 description 1
- XPUIMJZNQCEDCW-UHFFFAOYSA-N methyl 2-benzoyl-3-(4-cyanophenyl)-4-oxohexanoate Chemical compound C=1C=C(C#N)C=CC=1C(C(=O)CC)C(C(=O)OC)C(=O)C1=CC=CC=C1 XPUIMJZNQCEDCW-UHFFFAOYSA-N 0.000 description 1
- XJPXJTCUWCLADA-UHFFFAOYSA-N methyl 3-(3-nitrophenyl)-4-oxo-2-propanoylpentanoate Chemical compound CCC(=O)C(C(=O)OC)C(C(C)=O)C1=CC=CC([N+]([O-])=O)=C1 XJPXJTCUWCLADA-UHFFFAOYSA-N 0.000 description 1
- FBYNSFPIOIQCQM-UHFFFAOYSA-N methyl 3-ethyl-4-(3-nitrophenyl)-6-phenyl-1,4-dihydropyridazine-5-carboxylate Chemical compound CCC1=NNC(C=2C=CC=CC=2)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 FBYNSFPIOIQCQM-UHFFFAOYSA-N 0.000 description 1
- HTUMLCGRDQYDHM-UHFFFAOYSA-N methyl 4-(3-chlorophenyl)-3-(2-ethoxyethyl)-6-methyl-1,4-dihydropyridazine-5-carboxylate Chemical compound CCOCCC1=NNC(C)=C(C(=O)OC)C1C1=CC=CC(Cl)=C1 HTUMLCGRDQYDHM-UHFFFAOYSA-N 0.000 description 1
- PXFGPQAICFSHAF-UHFFFAOYSA-N methyl 4-(3-chlorophenyl)-6-methyl-3-phenyl-1,4-dihydropyridazine-5-carboxylate Chemical compound COC(=O)C1=C(C)NN=C(C=2C=CC=CC=2)C1C1=CC=CC(Cl)=C1 PXFGPQAICFSHAF-UHFFFAOYSA-N 0.000 description 1
- DLZVZNAPRCRXEG-UHFFFAOYSA-N methyl 4-oxobutanoate Chemical compound COC(=O)CCC=O DLZVZNAPRCRXEG-UHFFFAOYSA-N 0.000 description 1
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- JTXZXNXUQAZFEW-UHFFFAOYSA-N propan-2-yl 2-acetyl-3-(3-nitrophenyl)-4-oxohexanoate Chemical compound CC(C)OC(=O)C(C(C)=O)C(C(=O)CC)C1=CC=CC([N+]([O-])=O)=C1 JTXZXNXUQAZFEW-UHFFFAOYSA-N 0.000 description 1
- RQQKWJQWNRNAGM-UHFFFAOYSA-N propan-2-yl 2-acetyl-4-oxo-3-(4-propan-2-ylphenyl)heptanoate Chemical compound CC(C)OC(=O)C(C(C)=O)C(C(=O)CCC)C1=CC=C(C(C)C)C=C1 RQQKWJQWNRNAGM-UHFFFAOYSA-N 0.000 description 1
- RUEXTNXWZKGHGW-UHFFFAOYSA-N propan-2-yl 3,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridazine-5-carboxylate Chemical compound CC(C)OC(=O)C1=C(C)NN=C(C)C1C1=CC=CC=C1[N+]([O-])=O RUEXTNXWZKGHGW-UHFFFAOYSA-N 0.000 description 1
- WJKPHVJJFPCIGV-UHFFFAOYSA-N propan-2-yl 3,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridazine-5-carboxylate Chemical compound CC(C)OC(=O)C1=C(C)NN=C(C)C1C1=CC=CC([N+]([O-])=O)=C1 WJKPHVJJFPCIGV-UHFFFAOYSA-N 0.000 description 1
- SXQWGCMVWKNCIG-UHFFFAOYSA-N propan-2-yl 3-ethyl-6-methyl-4-(2-nitrophenyl)-1,4-dihydropyridazine-5-carboxylate Chemical compound CCC1=NNC(C)=C(C(=O)OC(C)C)C1C1=CC=CC=C1[N+]([O-])=O SXQWGCMVWKNCIG-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- YMEVCYQKKWSYRM-UHFFFAOYSA-N propyl 3,6-diethyl-4-(2-nitrophenyl)-1,4-dihydropyridazine-5-carboxylate Chemical compound CCCOC(=O)C1=C(CC)NN=C(CC)C1C1=CC=CC=C1[N+]([O-])=O YMEVCYQKKWSYRM-UHFFFAOYSA-N 0.000 description 1
- GWFWSNFWVPMVTQ-UHFFFAOYSA-N propyl 3-(2-ethylsulfanylethyl)-6-methyl-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridazine-5-carboxylate Chemical compound CCCOC(=O)C1=C(C)NN=C(CCSCC)C1C1=CC=CC=C1C(F)(F)F GWFWSNFWVPMVTQ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011787 zinc oxide 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
- 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)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772741260 DE2741260A1 (de) | 1977-09-14 | 1977-09-14 | Neue 1,4-dihydropyridazine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5455585A JPS5455585A (en) | 1979-05-02 |
| JPS6225661B2 true JPS6225661B2 (en, 2012) | 1987-06-04 |
Family
ID=6018878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11139078A Granted JPS5455585A (en) | 1977-09-14 | 1978-09-12 | Novel 1*44 dihydropiridazine compound |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4360520A (en, 2012) |
| EP (1) | EP0001108B1 (en, 2012) |
| JP (1) | JPS5455585A (en, 2012) |
| AT (1) | AT357549B (en, 2012) |
| DE (2) | DE2741260A1 (en, 2012) |
| ES (1) | ES473316A1 (en, 2012) |
| IT (1) | IT1099056B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4590194A (en) * | 1981-10-05 | 1986-05-20 | Sterling Drug Inc. | 3-[methyl or dimethyl)amino]-6-(pyridinyl)pyridazines and their cardiotonic use |
| DE3501855A1 (de) * | 1985-01-22 | 1986-07-24 | Bayer Ag, 5090 Leverkusen | 5-aryl-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
| US4833150A (en) * | 1985-03-14 | 1989-05-23 | Nelson Research & Development Co. | 1,4-dihydropyridines |
| GB8530602D0 (en) * | 1985-12-12 | 1986-01-22 | Fujisawa Pharmaceutical Co | Heterocyclic compounds |
| US4849436A (en) * | 1986-03-11 | 1989-07-18 | Nelson Research & Development Co. | 1,4-dihydropyridines |
| GB8818791D0 (en) * | 1988-08-08 | 1988-09-07 | Ici Plc | Azole derivatives |
| BE1030959B1 (nl) | 2022-10-12 | 2024-05-14 | Olivier Bv | Ecologische gedompelde gevelsteen |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3022305A (en) * | 1957-06-17 | 1962-02-20 | Du Pont | Process for preparing pyridazine derivatives and novel fluorine-containing pyridazine derivatives |
| US4011212A (en) * | 1974-05-13 | 1977-03-08 | American Home Products Corporation | 22-cyano-24-norcholanes |
| AT334133B (de) * | 1974-12-17 | 1976-12-27 | Chemie Linz Ag | Herbizides mittel |
-
1977
- 1977-09-14 DE DE19772741260 patent/DE2741260A1/de not_active Withdrawn
-
1978
- 1978-09-06 DE DE7878100826T patent/DE2860659D1/de not_active Expired
- 1978-09-06 EP EP78100826A patent/EP0001108B1/de not_active Expired
- 1978-09-11 US US05/941,527 patent/US4360520A/en not_active Expired - Lifetime
- 1978-09-12 IT IT27564/78A patent/IT1099056B/it active
- 1978-09-12 JP JP11139078A patent/JPS5455585A/ja active Granted
- 1978-09-13 ES ES473316A patent/ES473316A1/es not_active Expired
- 1978-09-14 AT AT665078A patent/AT357549B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES473316A1 (es) | 1979-05-16 |
| EP0001108B1 (de) | 1981-04-29 |
| ATA665078A (de) | 1979-12-15 |
| US4360520A (en) | 1982-11-23 |
| EP0001108A1 (de) | 1979-03-21 |
| DE2860659D1 (en) | 1981-08-06 |
| IT1099056B (it) | 1985-09-18 |
| AT357549B (de) | 1980-07-10 |
| JPS5455585A (en) | 1979-05-02 |
| IT7827564A0 (it) | 1978-09-12 |
| DE2741260A1 (de) | 1979-03-22 |
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