IE51271B1 - Novel dihydropyridazinones,their preparation and therapeutic agents containing these compounds - Google Patents
Novel dihydropyridazinones,their preparation and therapeutic agents containing these compoundsInfo
- Publication number
- IE51271B1 IE51271B1 IE1284/81A IE128481A IE51271B1 IE 51271 B1 IE51271 B1 IE 51271B1 IE 1284/81 A IE1284/81 A IE 1284/81A IE 128481 A IE128481 A IE 128481A IE 51271 B1 IE51271 B1 IE 51271B1
- Authority
- IE
- Ireland
- Prior art keywords
- carbon atoms
- methyl
- pyridazinone
- dihydro
- phenyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 42
- 239000003814 drug Substances 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 229940124597 therapeutic agent Drugs 0.000 title description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 19
- 229940079593 drug Drugs 0.000 claims abstract description 4
- 230000009424 thromboembolic effect Effects 0.000 claims abstract description 4
- -1 triiluoromethyl Chemical group 0.000 claims description 118
- 125000004432 carbon atom Chemical group C* 0.000 claims description 73
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 239000000460 chlorine Substances 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 6
- 150000002513 isocyanates Chemical class 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
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- 125000000304 alkynyl group Chemical group 0.000 claims description 5
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- 239000011737 fluorine Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 235000001014 amino acid Nutrition 0.000 claims description 4
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- PYBZUWHTGDCWSL-UHFFFAOYSA-N 2-amino-1-phenyl-4h-pyridazin-3-one Chemical compound C1=CCC(=O)N(N)N1C1=CC=CC=C1 PYBZUWHTGDCWSL-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
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- KSGYMLDMYPAMFV-UHFFFAOYSA-N 3-phenyl-4,5-dihydro-1h-pyridazin-6-one Chemical class N1C(=O)CCC(C=2C=CC=CC=2)=N1 KSGYMLDMYPAMFV-UHFFFAOYSA-N 0.000 abstract description 4
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- 239000002220 antihypertensive agent Substances 0.000 abstract description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract description 2
- GNVMUORYQLCPJZ-UHFFFAOYSA-N carbamothioic s-acid Chemical group NC(S)=O GNVMUORYQLCPJZ-UHFFFAOYSA-N 0.000 abstract description 2
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- 238000006243 chemical reaction Methods 0.000 description 20
- GDMRFHZLKNYRRO-UHFFFAOYSA-N 3-(4-aminophenyl)-4-methyl-4,5-dihydro-1h-pyridazin-6-one Chemical compound CC1CC(=O)NN=C1C1=CC=C(N)C=C1 GDMRFHZLKNYRRO-UHFFFAOYSA-N 0.000 description 13
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 13
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
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- 239000002253 acid Substances 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
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- 229910052623 talc Inorganic materials 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- GXBSYUMCIFBIPI-UHFFFAOYSA-N cyclobutyl n-[4-(4-methyl-6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]carbamate Chemical compound CC1CC(=O)NN=C1C(C=C1)=CC=C1NC(=O)OC1CCC1 GXBSYUMCIFBIPI-UHFFFAOYSA-N 0.000 description 2
- RBNOANMZMPAQQP-UHFFFAOYSA-N cyclohexylmethyl n-[4-(4-methyl-6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]carbamate Chemical compound CC1CC(=O)NN=C1C(C=C1)=CC=C1NC(=O)OCC1CCCCC1 RBNOANMZMPAQQP-UHFFFAOYSA-N 0.000 description 2
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- 238000000354 decomposition reaction Methods 0.000 description 2
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- 125000006628 propoxycarbonylamino group Chemical group 0.000 description 1
- QQKDTTWZXHEGAQ-UHFFFAOYSA-N propyl carbonochloridate Chemical compound CCCOC(Cl)=O QQKDTTWZXHEGAQ-UHFFFAOYSA-N 0.000 description 1
- LEEQDBNTHRUXCJ-UHFFFAOYSA-N propyl n-[4-(4-methyl-6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]carbamate Chemical compound C1=CC(NC(=O)OCCC)=CC=C1C1=NNC(=O)CC1C LEEQDBNTHRUXCJ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- UVNFIGDPQSSDQS-UHFFFAOYSA-N s-(4-chlorophenyl) n-[4-(4-methyl-6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]carbamothioate Chemical compound CC1CC(=O)NN=C1C(C=C1)=CC=C1NC(=O)SC1=CC=C(Cl)C=C1 UVNFIGDPQSSDQS-UHFFFAOYSA-N 0.000 description 1
- LDQNOCNSVILFDQ-UHFFFAOYSA-N s-(4-cyanophenyl) n-[4-(4-methyl-6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]carbamothioate Chemical compound CC1CC(=O)NN=C1C(C=C1)=CC=C1NC(=O)SC1=CC=C(C#N)C=C1 LDQNOCNSVILFDQ-UHFFFAOYSA-N 0.000 description 1
- JKJGKNMSZMZPKX-UHFFFAOYSA-N s-(cyclobutylmethyl) n-[4-(4-methyl-6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]carbamothioate Chemical compound CC1CC(=O)NN=C1C(C=C1)=CC=C1NC(=O)SCC1CCC1 JKJGKNMSZMZPKX-UHFFFAOYSA-N 0.000 description 1
- YGKBSLYSDBTXLG-UHFFFAOYSA-N s-[3-(trifluoromethyl)phenyl] n-[4-(4-methyl-6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]carbamothioate Chemical compound CC1CC(=O)NN=C1C(C=C1)=CC=C1NC(=O)SC1=CC=CC(C(F)(F)F)=C1 YGKBSLYSDBTXLG-UHFFFAOYSA-N 0.000 description 1
- LFHWQVRZDHYSJU-UHFFFAOYSA-N s-benzyl n-[4-(4-methyl-6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]carbamothioate Chemical compound CC1CC(=O)NN=C1C(C=C1)=CC=C1NC(=O)SCC1=CC=CC=C1 LFHWQVRZDHYSJU-UHFFFAOYSA-N 0.000 description 1
- FZOUSCQSBPAXPT-UHFFFAOYSA-N s-butyl n-[4-(4-methyl-6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]carbamothioate Chemical compound C1=CC(NC(=O)SCCCC)=CC=C1C1=NNC(=O)CC1C FZOUSCQSBPAXPT-UHFFFAOYSA-N 0.000 description 1
- IHEAHQPFTOEHJA-UHFFFAOYSA-N s-cyclohexyl n-[4-(4-methyl-6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]carbamothioate Chemical compound CC1CC(=O)NN=C1C(C=C1)=CC=C1NC(=O)SC1CCCCC1 IHEAHQPFTOEHJA-UHFFFAOYSA-N 0.000 description 1
- QCMHWZUFWLOOGI-UHFFFAOYSA-N s-ethyl chloromethanethioate Chemical compound CCSC(Cl)=O QCMHWZUFWLOOGI-UHFFFAOYSA-N 0.000 description 1
- LQJJJJPCMLPIJH-UHFFFAOYSA-N s-phenyl n-[4-(4-methyl-6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]carbamothioate Chemical compound CC1CC(=O)NN=C1C(C=C1)=CC=C1NC(=O)SC1=CC=CC=C1 LQJJJJPCMLPIJH-UHFFFAOYSA-N 0.000 description 1
- NSCWFJYBAOBNIM-UHFFFAOYSA-N s-propan-2-yl n-[4-(4-methyl-6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]carbamothioate Chemical compound C1=CC(NC(=O)SC(C)C)=CC=C1C1=NNC(=O)CC1C NSCWFJYBAOBNIM-UHFFFAOYSA-N 0.000 description 1
- FYOPSYJKEHWOBR-UHFFFAOYSA-N s-propyl chloromethanethioate Chemical compound CCCSC(Cl)=O FYOPSYJKEHWOBR-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- SYRHIZPPCHMRIT-UHFFFAOYSA-N tin(4+) Chemical compound [Sn+4] SYRHIZPPCHMRIT-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 238000005303 weighing Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803022177 DE3022177A1 (de) | 1980-06-13 | 1980-06-13 | Neue dihydropyridazinone, verfahren zu ihrer herstellung und diese verbindung enthaltende therapeutische mittel |
| DE19803033702 DE3033702A1 (de) | 1980-09-08 | 1980-09-08 | Neue dihydropyridazinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende therapeutische mittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE811284L IE811284L (en) | 1981-12-13 |
| IE51271B1 true IE51271B1 (en) | 1986-11-26 |
Family
ID=25785986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1284/81A IE51271B1 (en) | 1980-06-13 | 1981-06-10 | Novel dihydropyridazinones,their preparation and therapeutic agents containing these compounds |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4415571A (en:Method) |
| EP (1) | EP0042513B1 (en:Method) |
| CA (1) | CA1163268A (en:Method) |
| DE (1) | DE3165383D1 (en:Method) |
| DK (1) | DK148536C (en:Method) |
| ES (1) | ES503007A0 (en:Method) |
| GR (1) | GR81309B (en:Method) |
| IE (1) | IE51271B1 (en:Method) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3302021A1 (de) * | 1983-01-22 | 1984-07-26 | Basf Ag, 6700 Ludwigshafen | 6-aryl-4,5-dihydro-3(2h)-pyridazinone, ihre herstellung und verwendung |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670158U (de) | 1953-11-05 | 1954-01-14 | Gustav Fey | Vorrichtung zur erfassung und verteilung von versand- und oder lagergut. |
| DE1670043C3 (de) * | 1966-01-07 | 1975-05-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von 3-(Aminophenyl)-pyridazon-(6)-derivaten |
| US3689652A (en) * | 1970-10-09 | 1972-09-05 | William Vincent Curran | Method of lowering blood pressure in mammals |
| IL37788A0 (en) | 1970-10-09 | 1971-12-29 | American Cyanamid Co | New pyridazinone compounds,their preparation and pharmaceutical compositions containing them |
| DE2123246C2 (de) * | 1971-05-11 | 1982-11-25 | Basf Ag, 6700 Ludwigshafen | 6-[p-(β-Phenyläthylaminoacetylamino)-phenyl]-4,5-dihydropyridazon-(3) |
| BE791539A (fr) | 1971-11-19 | 1973-05-17 | Basf Ag | Dihydropyridazones, leur preparation et leurs utilisations therapeutiques |
| US3888901A (en) * | 1972-07-20 | 1975-06-10 | American Cyanamid Co | Process of preparing 3-alkyl-3-(benzoyl)propionitriles |
| US3824271A (en) * | 1972-07-20 | 1974-07-16 | American Cyanamid Co | 3-alkyl-3-(benzoyl)propionitriles |
| DE2304977A1 (de) | 1973-02-01 | 1974-08-08 | Basf Ag | Neue dihydropyridazinone |
| US4011321A (en) * | 1973-12-19 | 1977-03-08 | Smith Kline & French Laboratories Limited | Pharmaceutical compositions and methods of inhibiting β-adrenergic receptors |
| DE2727481A1 (de) * | 1977-06-18 | 1979-01-11 | Basf Ag | Dihydropyridazone und dihydropyridazone enthaltende therapeutische mittel |
-
1981
- 1981-06-01 GR GR65114A patent/GR81309B/el unknown
- 1981-06-03 EP EP81104262A patent/EP0042513B1/de not_active Expired
- 1981-06-03 DE DE8181104262T patent/DE3165383D1/de not_active Expired
- 1981-06-04 CA CA000379001A patent/CA1163268A/en not_active Expired
- 1981-06-09 US US06/272,016 patent/US4415571A/en not_active Expired - Fee Related
- 1981-06-10 IE IE1284/81A patent/IE51271B1/en unknown
- 1981-06-12 DK DK257481A patent/DK148536C/da not_active IP Right Cessation
- 1981-06-12 ES ES503007A patent/ES503007A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4415571A (en) | 1983-11-15 |
| GR81309B (en:Method) | 1984-12-11 |
| DK257481A (da) | 1981-12-14 |
| ES8203854A1 (es) | 1982-04-01 |
| DK148536C (da) | 1986-01-06 |
| IE811284L (en) | 1981-12-13 |
| DK148536B (da) | 1985-07-29 |
| DE3165383D1 (en) | 1984-09-13 |
| CA1163268A (en) | 1984-03-06 |
| EP0042513A1 (de) | 1981-12-30 |
| ES503007A0 (es) | 1982-04-01 |
| EP0042513B1 (de) | 1984-08-08 |
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