PL85023B1 - - Google Patents
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- Publication number
- PL85023B1 PL85023B1 PL15148071A PL15148071A PL85023B1 PL 85023 B1 PL85023 B1 PL 85023B1 PL 15148071 A PL15148071 A PL 15148071A PL 15148071 A PL15148071 A PL 15148071A PL 85023 B1 PL85023 B1 PL 85023B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- hydrogen
- pyridazine
- group
- carbon atoms
- Prior art date
Links
- -1 alkyl radical Chemical class 0.000 claims description 61
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- WUYWHIAAQYQKPP-UHFFFAOYSA-N 4-(4-fluorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=C(F)C=C1 WUYWHIAAQYQKPP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N 2-butanol Substances CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 3
- UIUJIQZEACWQSV-UHFFFAOYSA-N succinic semialdehyde Chemical class OC(=O)CCC=O UIUJIQZEACWQSV-UHFFFAOYSA-N 0.000 claims 2
- HECCMMXKNZDUIU-UHFFFAOYSA-N 4-(4-chloro-3-methylphenyl)-4-oxobutanoic acid Chemical compound CC1=CC(C(=O)CCC(O)=O)=CC=C1Cl HECCMMXKNZDUIU-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- AHVASTJJVAYFPY-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=C(Cl)C=C1 AHVASTJJVAYFPY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000008101 lactose 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
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- VEKNDVUXPJNTKO-UHFFFAOYSA-N 1-[6-(3,4-dichlorophenyl)-4,5-dihydro-3h-pyridazin-2-yl]butan-2-ol Chemical compound CCC(O)CN1CCCC(C=2C=C(Cl)C(Cl)=CC=2)=N1 VEKNDVUXPJNTKO-UHFFFAOYSA-N 0.000 description 1
- YYSAKKZGEBXBJQ-UHFFFAOYSA-N 1-[6-(4-chloro-3-methylphenyl)-4,5-dihydro-3h-pyridazin-2-yl]butan-2-ol Chemical compound CCC(O)CN1CCCC(C=2C=C(C)C(Cl)=CC=2)=N1 YYSAKKZGEBXBJQ-UHFFFAOYSA-N 0.000 description 1
- AULZDVDDOZKZTN-UHFFFAOYSA-N 1-[6-(4-chlorophenyl)-5-methyl-4,5-dihydro-3h-pyridazin-2-yl]butan-2-ol Chemical compound CCC(O)CN1CCC(C)C(C=2C=CC(Cl)=CC=2)=N1 AULZDVDDOZKZTN-UHFFFAOYSA-N 0.000 description 1
- CMEQJPXCKNXIMV-UHFFFAOYSA-N 1-[6-[4-(trifluoromethyl)phenyl]-4,5-dihydro-3h-pyridazin-2-yl]butan-2-ol Chemical compound CCC(O)CN1CCCC(C=2C=CC(=CC=2)C(F)(F)F)=N1 CMEQJPXCKNXIMV-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- OOGIJSSRJQGXTD-UHFFFAOYSA-N 2-hydrazinylbutan-1-ol Chemical compound CCC(CO)NN OOGIJSSRJQGXTD-UHFFFAOYSA-N 0.000 description 1
- URVPGNYASAJNEJ-UHFFFAOYSA-N 2-methyl-3-oxo-3-pyridin-3-ylpropanoic acid Chemical compound OC(=O)C(C)C(=O)C1=CC=CN=C1 URVPGNYASAJNEJ-UHFFFAOYSA-N 0.000 description 1
- MSAKIUWZXWJSRV-UHFFFAOYSA-N 2-methyl-3-oxo-3-thiophen-2-ylpropanoic acid Chemical compound OC(=O)C(C)C(=O)C1=CC=CS1 MSAKIUWZXWJSRV-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- ITJYXMCBBGPWDH-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=C(Cl)C=C1Cl ITJYXMCBBGPWDH-UHFFFAOYSA-N 0.000 description 1
- DPCXOOJTAKKWIC-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=C(Cl)C(Cl)=C1 DPCXOOJTAKKWIC-UHFFFAOYSA-N 0.000 description 1
- GLNOAEGCWGDNDG-UHFFFAOYSA-N 4-oxo-4-[3-(trifluoromethyl)phenyl]butanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=CC(C(F)(F)F)=C1 GLNOAEGCWGDNDG-UHFFFAOYSA-N 0.000 description 1
- XBTRBFQQDDYMFC-UHFFFAOYSA-N 4-oxo-4-[4-(trifluoromethyl)phenyl]butanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=C(C(F)(F)F)C=C1 XBTRBFQQDDYMFC-UHFFFAOYSA-N 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 101100028482 Caenorhabditis elegans pal-1 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 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 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- 206010049816 Muscle tightness Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical class CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 210000005227 renal system Anatomy 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 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
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8897670A | 1970-11-12 | 1970-11-12 | |
| US16656571A | 1971-07-27 | 1971-07-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL85023B1 true PL85023B1 (OSRAM) | 1976-04-30 |
Family
ID=26779241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL15148071A PL85023B1 (OSRAM) | 1970-11-12 | 1971-11-10 |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5616148B1 (OSRAM) |
| DD (1) | DD95846A5 (OSRAM) |
| DK (1) | DK135121B (OSRAM) |
| ES (2) | ES396873A1 (OSRAM) |
| HU (1) | HU162865B (OSRAM) |
| PL (1) | PL85023B1 (OSRAM) |
-
1971
- 1971-11-10 ES ES396873A patent/ES396873A1/es not_active Expired
- 1971-11-10 DK DK550371A patent/DK135121B/da unknown
- 1971-11-10 HU HUSA002274 patent/HU162865B/hu unknown
- 1971-11-10 PL PL15148071A patent/PL85023B1/pl unknown
- 1971-11-10 JP JP8915171A patent/JPS5616148B1/ja active Pending
- 1971-11-11 DD DD15887571A patent/DD95846A5/xx unknown
-
1974
- 1974-03-16 ES ES424356A patent/ES424356A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK135121B (da) | 1977-03-07 |
| HU162865B (OSRAM) | 1973-04-28 |
| ES396873A1 (es) | 1975-03-01 |
| DD95846A5 (OSRAM) | 1973-02-20 |
| DK135121C (OSRAM) | 1977-08-08 |
| ES424356A1 (es) | 1976-10-16 |
| JPS5616148B1 (OSRAM) | 1981-04-14 |
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