NO773245L - Fremgangsmaate for fremstilling av nye triazolopyridaziner - Google Patents
Fremgangsmaate for fremstilling av nye triazolopyridazinerInfo
- Publication number
- NO773245L NO773245L NO773245A NO773245A NO773245L NO 773245 L NO773245 L NO 773245L NO 773245 A NO773245 A NO 773245A NO 773245 A NO773245 A NO 773245A NO 773245 L NO773245 L NO 773245L
- Authority
- NO
- Norway
- Prior art keywords
- hydrogen
- methyl
- trifluoromethyl
- group
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 145
- 238000002360 preparation method Methods 0.000 claims description 113
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 82
- 239000001257 hydrogen Substances 0.000 claims description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims description 67
- 229910052794 bromium Inorganic materials 0.000 claims description 49
- 239000002904 solvent Substances 0.000 claims description 42
- 238000010992 reflux Methods 0.000 claims description 41
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
- -1 nitro, amino, acetamido, carbamoyl Chemical group 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 239000000460 chlorine Substances 0.000 claims description 29
- 229910052801 chlorine Inorganic materials 0.000 claims description 28
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 27
- 239000011737 fluorine Substances 0.000 claims description 27
- 229910052731 fluorine Inorganic materials 0.000 claims description 27
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 25
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 14
- 241000124008 Mammalia Species 0.000 claims description 13
- 230000037396 body weight Effects 0.000 claims description 11
- 150000007513 acids Chemical class 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 230000001225 therapeutic effect Effects 0.000 claims description 6
- 206010020772 Hypertension Diseases 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- 150000002905 orthoesters Chemical class 0.000 claims description 5
- 150000001805 chlorine compounds Chemical class 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 238000013019 agitation Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 5
- 150000008064 anhydrides Chemical class 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- 208000001431 Psychomotor Agitation Diseases 0.000 claims 1
- 206010038743 Restlessness Diseases 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 163
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 138
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 131
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 123
- 239000013078 crystal Substances 0.000 description 120
- 239000007787 solid Substances 0.000 description 119
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 103
- 239000000243 solution Substances 0.000 description 89
- 239000000047 product Substances 0.000 description 88
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 74
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 70
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- 239000011541 reaction mixture Substances 0.000 description 63
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
- 235000019441 ethanol Nutrition 0.000 description 50
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 229960000583 acetic acid Drugs 0.000 description 41
- 238000003756 stirring Methods 0.000 description 35
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 description 32
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 31
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 28
- 239000000706 filtrate Substances 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- 238000001914 filtration Methods 0.000 description 27
- 239000000463 material Substances 0.000 description 27
- 239000003921 oil Substances 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 235000011054 acetic acid Nutrition 0.000 description 21
- 239000003208 petroleum Substances 0.000 description 21
- 239000012362 glacial acetic acid Substances 0.000 description 20
- 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
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 19
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 18
- 239000006071 cream Substances 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 239000003480 eluent Substances 0.000 description 15
- 238000001953 recrystallisation Methods 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 14
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 14
- 239000000391 magnesium silicate Substances 0.000 description 14
- 229910052919 magnesium silicate Inorganic materials 0.000 description 14
- 235000019792 magnesium silicate Nutrition 0.000 description 14
- 241000700159 Rattus Species 0.000 description 13
- 239000002244 precipitate Substances 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 235000008504 concentrate Nutrition 0.000 description 10
- 239000012141 concentrate Substances 0.000 description 10
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 9
- BUBRFWDEAVIFMV-UHFFFAOYSA-N 3-chloro-6-phenylpyridazine Chemical compound N1=NC(Cl)=CC=C1C1=CC=CC=C1 BUBRFWDEAVIFMV-UHFFFAOYSA-N 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 7
- 239000012065 filter cake Substances 0.000 description 7
- 239000005457 ice water Substances 0.000 description 7
- 229920002261 Corn starch Polymers 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 239000008120 corn starch Substances 0.000 description 6
- 229940099112 cornstarch Drugs 0.000 description 6
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 231100000252 nontoxic Toxicity 0.000 description 6
- 230000003000 nontoxic effect Effects 0.000 description 6
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 5
- 239000002249 anxiolytic agent Substances 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- DXGIRFAFSFKYCF-UHFFFAOYSA-N propanehydrazide Chemical compound CCC(=O)NN DXGIRFAFSFKYCF-UHFFFAOYSA-N 0.000 description 5
- 238000007363 ring formation reaction Methods 0.000 description 5
- 230000035939 shock Effects 0.000 description 5
- 239000006188 syrup Substances 0.000 description 5
- 235000020357 syrup Nutrition 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
- 230000000049 anti-anxiety effect Effects 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000004042 decolorization Methods 0.000 description 4
- 230000035622 drinking Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 4
- 239000002198 insoluble material Substances 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 230000007306 turnover Effects 0.000 description 4
- 239000008215 water for injection Substances 0.000 description 4
- YDLINUGLEXXXOL-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-6-chloropyridazine Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC=C(Cl)N=N1 YDLINUGLEXXXOL-UHFFFAOYSA-N 0.000 description 3
- FEDFSKWDQHFDNV-UHFFFAOYSA-N 3-[4-nitro-3-(trifluoromethyl)phenyl]-1h-pyridazin-6-one Chemical compound C1=C(C(F)(F)F)C([N+](=O)[O-])=CC=C1C1=NNC(=O)C=C1 FEDFSKWDQHFDNV-UHFFFAOYSA-N 0.000 description 3
- UTCVANDFQGNDKQ-UHFFFAOYSA-N 3-chloro-6-(2-chlorophenyl)pyridazine Chemical compound N1=NC(Cl)=CC=C1C1=CC=CC=C1Cl UTCVANDFQGNDKQ-UHFFFAOYSA-N 0.000 description 3
- VSJCZKWUVAOYPD-UHFFFAOYSA-N 3-chloro-6-(2-fluorophenyl)pyridazine Chemical compound FC1=CC=CC=C1C1=CC=C(Cl)N=N1 VSJCZKWUVAOYPD-UHFFFAOYSA-N 0.000 description 3
- MIZBDHFLBBSBFA-UHFFFAOYSA-N 3-chloro-6-(3,4-dichlorophenyl)pyridazine Chemical compound N1=NC(Cl)=CC=C1C1=CC=C(Cl)C(Cl)=C1 MIZBDHFLBBSBFA-UHFFFAOYSA-N 0.000 description 3
- QRFJVCQGPISREA-UHFFFAOYSA-N 3-chloro-6-(3-chlorophenyl)pyridazine Chemical compound ClC1=CC=CC(C=2N=NC(Cl)=CC=2)=C1 QRFJVCQGPISREA-UHFFFAOYSA-N 0.000 description 3
- ARQKIDKGCMDXKY-UHFFFAOYSA-N 3-chloro-6-(4-chlorophenyl)pyridazine Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(Cl)N=N1 ARQKIDKGCMDXKY-UHFFFAOYSA-N 0.000 description 3
- KSGYMLDMYPAMFV-UHFFFAOYSA-N 3-phenyl-4,5-dihydro-1h-pyridazin-6-one Chemical compound N1C(=O)CCC(C=2C=CC=CC=2)=N1 KSGYMLDMYPAMFV-UHFFFAOYSA-N 0.000 description 3
- 206010010904 Convulsion Diseases 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 230000004872 arterial blood pressure Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 3
- 239000003182 parenteral nutrition solution Substances 0.000 description 3
- 229960005152 pentetrazol Drugs 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- SEHSCBSQNGYKBH-UHFFFAOYSA-N 2,3-dimethyl-4-oxo-4-phenylbutanoic acid Chemical compound OC(=O)C(C)C(C)C(=O)C1=CC=CC=C1 SEHSCBSQNGYKBH-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- YRWWFLYKKZTALE-UHFFFAOYSA-N 3-(3-chlorophenyl)-1h-pyridazin-6-one Chemical compound ClC1=CC=CC(C2=NNC(=O)C=C2)=C1 YRWWFLYKKZTALE-UHFFFAOYSA-N 0.000 description 2
- PECLXFKVDLLXHC-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-methyl-1h-pyridazin-6-one Chemical compound N1C(=O)C(C)=CC(C=2C=C(Cl)C=CC=2)=N1 PECLXFKVDLLXHC-UHFFFAOYSA-N 0.000 description 2
- JJICVFGADMKYOH-UHFFFAOYSA-N 3-(3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)aniline Chemical compound N=1N2C(C)=NN=C2C=CC=1C1=CC=CC(N)=C1 JJICVFGADMKYOH-UHFFFAOYSA-N 0.000 description 2
- OGOKDAMJYJGOGG-UHFFFAOYSA-N 3-(4-bromophenyl)-6-chloro-4-methylpyridazine Chemical compound CC1=CC(Cl)=NN=C1C1=CC=C(Br)C=C1 OGOKDAMJYJGOGG-UHFFFAOYSA-N 0.000 description 2
- SWHBEWAGUFMFCG-UHFFFAOYSA-N 3-chloro-6-(3-fluorophenyl)pyridazine Chemical compound FC1=CC=CC(C=2N=NC(Cl)=CC=2)=C1 SWHBEWAGUFMFCG-UHFFFAOYSA-N 0.000 description 2
- IEIFRHAHAWOUJM-UHFFFAOYSA-N 3-chloro-6-(3-methylphenyl)pyridazine Chemical compound CC1=CC=CC(C=2N=NC(Cl)=CC=2)=C1 IEIFRHAHAWOUJM-UHFFFAOYSA-N 0.000 description 2
- MXWVARQFOWFFLN-UHFFFAOYSA-N 3-chloro-6-(4-chlorophenyl)-4-methylpyridazine Chemical compound N1=C(Cl)C(C)=CC(C=2C=CC(Cl)=CC=2)=N1 MXWVARQFOWFFLN-UHFFFAOYSA-N 0.000 description 2
- LYFFDJDAWPESSH-UHFFFAOYSA-N 3-chloro-6-(4-fluorophenyl)pyridazine Chemical compound C1=CC(F)=CC=C1C1=CC=C(Cl)N=N1 LYFFDJDAWPESSH-UHFFFAOYSA-N 0.000 description 2
- IHQWZEPMXYRPAE-UHFFFAOYSA-N 3-chloro-6-[2-chloro-5-(trifluoromethyl)phenyl]pyridazine Chemical compound FC(F)(F)C1=CC=C(Cl)C(C=2N=NC(Cl)=CC=2)=C1 IHQWZEPMXYRPAE-UHFFFAOYSA-N 0.000 description 2
- TVWOBKTURBXCNX-UHFFFAOYSA-N 3-chloro-6-[3-(trifluoromethyl)phenyl]pyridazine Chemical compound FC(F)(F)C1=CC=CC(C=2N=NC(Cl)=CC=2)=C1 TVWOBKTURBXCNX-UHFFFAOYSA-N 0.000 description 2
- HVQDTPPEBOALHZ-UHFFFAOYSA-N 3-chloro-6-[4-(trifluoromethyl)phenyl]pyridazine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(Cl)N=N1 HVQDTPPEBOALHZ-UHFFFAOYSA-N 0.000 description 2
- UKDBJXKGRKMNHV-UHFFFAOYSA-N 3-chloro-6-[4-fluoro-3-(trifluoromethyl)phenyl]pyridazine Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1C1=CC=C(Cl)N=N1 UKDBJXKGRKMNHV-UHFFFAOYSA-N 0.000 description 2
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- WAWREFIHVNQSMF-UHFFFAOYSA-N [5-(3-chlorophenyl)pyridin-2-yl]hydrazine Chemical compound C1=NC(NN)=CC=C1C1=CC=CC(Cl)=C1 WAWREFIHVNQSMF-UHFFFAOYSA-N 0.000 description 1
- AZCTXHPEZWKVGD-UHFFFAOYSA-N [6-(4-chlorophenyl)pyridazin-3-yl]hydrazine Chemical compound N1=NC(NN)=CC=C1C1=CC=C(Cl)C=C1 AZCTXHPEZWKVGD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
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- 239000006286 aqueous extract Substances 0.000 description 1
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- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
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- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
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- ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
- 229960004782 chlordiazepoxide Drugs 0.000 description 1
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- NKKMVIVFRUYPLQ-NSCUHMNNSA-N crotononitrile Chemical compound C\C=C\C#N NKKMVIVFRUYPLQ-NSCUHMNNSA-N 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
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- HOTCHIFVNVTGLD-UHFFFAOYSA-N ethyl 4-cyano-4-morpholin-4-yl-4-[4-(trifluoromethyl)phenyl]butanoate Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(C#N)(CCC(=O)OCC)N1CCOCC1 HOTCHIFVNVTGLD-UHFFFAOYSA-N 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
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- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
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- 239000000174 gluconic acid Substances 0.000 description 1
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- ZTOMUSMDRMJOTH-UHFFFAOYSA-N glutaronitrile Chemical compound N#CCCCC#N ZTOMUSMDRMJOTH-UHFFFAOYSA-N 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
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- 239000003701 inert diluent Substances 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
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- 230000000977 initiatory effect Effects 0.000 description 1
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- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000002642 intravenous therapy Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229960004194 lidocaine Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- OVWYEQOVUDKZNU-UHFFFAOYSA-N m-tolualdehyde Chemical compound CC1=CC=CC(C=O)=C1 OVWYEQOVUDKZNU-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- SFXVCOHTHWLESF-UHFFFAOYSA-N n-[3-(7-methyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2C(=CC3=NN=CN3N=2)C)=C1 SFXVCOHTHWLESF-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 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
- YLLIGHVCTUPGEH-UHFFFAOYSA-M potassium;ethanol;hydroxide Chemical compound [OH-].[K+].CCO YLLIGHVCTUPGEH-UHFFFAOYSA-M 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 229940116317 potato starch Drugs 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 239000002994 raw material Substances 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
- 235000019204 saccharin Nutrition 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000004208 shellac Substances 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
- 235000013874 shellac Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- LJRGBERXYNQPJI-UHFFFAOYSA-M sodium;3-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 LJRGBERXYNQPJI-UHFFFAOYSA-M 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
-
- 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
-
- 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
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/08—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/12—Halogen atoms or nitro radicals
-
- 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
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/14—Oxygen atoms
-
- 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
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/20—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Anesthesiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/725,597 US4230705A (en) | 1976-09-22 | 1976-09-22 | 6-Phenyl-1,2,4-triazolo[4,3-b]pyridazines and their uses in treating anxiety |
US73039576A | 1976-10-07 | 1976-10-07 | |
US73547576A | 1976-10-26 | 1976-10-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
NO773245L true NO773245L (no) | 1978-03-28 |
Family
ID=27419081
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO773245A NO773245L (no) | 1976-09-22 | 1977-09-21 | Fremgangsmaate for fremstilling av nye triazolopyridaziner |
Country Status (19)
Country | Link |
---|---|
JP (1) | JPS5340798A (fr) |
AR (2) | AR218036A1 (fr) |
AT (1) | AT360034B (fr) |
AU (1) | AU513760B2 (fr) |
BG (1) | BG29287A3 (fr) |
CA (1) | CA1080712A (fr) |
DD (1) | DD132586A5 (fr) |
DE (1) | DE2741763A1 (fr) |
DK (1) | DK417377A (fr) |
ES (3) | ES462543A1 (fr) |
FI (1) | FI772802A (fr) |
FR (1) | FR2442848A1 (fr) |
GB (1) | GB1589237A (fr) |
GR (1) | GR71699B (fr) |
LU (1) | LU78150A1 (fr) |
NL (1) | NL7710389A (fr) |
NO (1) | NO773245L (fr) |
PT (1) | PT67067B (fr) |
RO (1) | RO72226A (fr) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GR70309B (fr) * | 1979-10-29 | 1982-09-08 | Dow Chemical Co | |
FR2473522A1 (fr) * | 1980-01-16 | 1981-07-17 | Synthelabo | Nouveaux derives substitues de dihydro-2,3 imidazo(1,2-b)pyridazines et les medicaments, utiles notamment comme antidepresseurs, qui en contiennent |
EP0036711B1 (fr) * | 1980-03-22 | 1985-12-04 | Fbc Limited | Composés hétérocycliques pesticides, procédés pour leur préparation, compositions les contenant, et leur utilisation |
DE3217325A1 (de) * | 1982-05-08 | 1983-11-10 | Hoechst Ag, 6230 Frankfurt | 3-amino-6-aryl-1,2,4-triazolo(4,3-b)-pyridazine, ihre herstellung und ihre verwendung |
US4487930A (en) * | 1982-09-07 | 1984-12-11 | The Dow Chemical Company | 6-[(Cyclic amino)alkylamino]-tetrahydrotriazolo[3,4-a]phthalazines |
FR2562071B1 (fr) * | 1984-03-30 | 1986-12-19 | Sanofi Sa | Triazolo(4,3-b)pyridazines, procede pour leur preparation et compositions pharmaceutiques les contenant |
US4654343A (en) * | 1985-10-31 | 1987-03-31 | American Cyanamid Company | N-substituted-N[3-(1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]alkanamides, carbamates and ureas |
US4767765A (en) * | 1985-10-31 | 1988-08-30 | American Cyanamid Company | N-substituted-N-[3-(1,2,4-triazolo-[4,3-b]pyridazin-6-yl)phenyl]alkanamides, carbamates and ureas |
BR9710729A (pt) | 1996-07-25 | 1999-08-17 | Merck Sharp & Dohme | Composto composi-Æo farmac-utica utiliza-Æo de um composto e processo para o tratamento e/ou a preven-Æo da ansiedade e de convuls{es para a triagem de compostos ansioliticos nÆo-sedativos e para a prepara-Æo de um composto |
WO1999036423A1 (fr) * | 1998-01-14 | 1999-07-22 | Merck Sharp & Dohme Limited | Derives de triazolo-pyridazine utiles comme ligands des recepteurs gaba |
CZ290883B6 (cs) | 1998-01-21 | 2002-11-13 | Merck Sharp And Dohme Limited | Triazolopyridazinové deriváty, způsob jejich výroby a farmaceutický prostředek je obsahující |
GB9801208D0 (en) * | 1998-01-21 | 1998-03-18 | Merck Sharp & Dohme | Therapeutic agents |
GB9801202D0 (en) * | 1998-01-21 | 1998-03-18 | Merck Sharp & Dohme | Therapeutic agents |
GB9801210D0 (en) | 1998-01-21 | 1998-03-18 | Merck Sharp & Dohme | Therapeutic agents |
GB9801234D0 (en) | 1998-01-21 | 1998-03-18 | Merck Sharp & Dohme | Therapeutic agents |
GB9801397D0 (en) | 1998-01-22 | 1998-03-18 | Merck Sharp & Dohme | Therapeutic agents |
GB9801538D0 (en) | 1998-01-23 | 1998-03-25 | Merck Sharp & Dohme | Pharmaceutical product |
WO2005077953A1 (fr) * | 2004-02-18 | 2005-08-25 | Banyu Pharmaceutical Co., Ltd. | Dérivé azoté de noyau hétéroaromatique fusionné |
JP7105797B2 (ja) * | 2016-11-28 | 2022-07-25 | プラクシス プレシジョン メディシンズ, インコーポレイテッド | 化合物及びその使用方法 |
US11866439B2 (en) | 2018-05-30 | 2024-01-09 | Praxis Precision Medicines, Inc. | Ion channel modulators |
US11773099B2 (en) | 2019-05-28 | 2023-10-03 | Praxis Precision Medicines, Inc. | Compounds and their methods of use |
US11505554B2 (en) | 2019-05-31 | 2022-11-22 | Praxis Precision Medicines, Inc. | Substituted pyridines as ion channel modulators |
-
1977
- 1977-08-16 CA CA284,806A patent/CA1080712A/fr not_active Expired
- 1977-08-19 GR GR54197A patent/GR71699B/el unknown
- 1977-09-07 AR AR269126A patent/AR218036A1/es active
- 1977-09-16 DE DE19772741763 patent/DE2741763A1/de not_active Withdrawn
- 1977-09-20 BG BG037371A patent/BG29287A3/xx unknown
- 1977-09-20 RO RO7791618A patent/RO72226A/fr unknown
- 1977-09-20 LU LU78150A patent/LU78150A1/xx unknown
- 1977-09-21 AT AT677577A patent/AT360034B/de not_active IP Right Cessation
- 1977-09-21 DK DK417377A patent/DK417377A/da unknown
- 1977-09-21 NO NO773245A patent/NO773245L/no unknown
- 1977-09-21 AU AU28995/77A patent/AU513760B2/en not_active Expired
- 1977-09-22 NL NL7710389A patent/NL7710389A/xx not_active Application Discontinuation
- 1977-09-22 ES ES462543A patent/ES462543A1/es not_active Expired
- 1977-09-22 DD DD7700201157A patent/DD132586A5/xx unknown
- 1977-09-22 JP JP11344877A patent/JPS5340798A/ja active Pending
- 1977-09-22 FI FI772802A patent/FI772802A/fi not_active Application Discontinuation
- 1977-09-22 PT PT67067A patent/PT67067B/pt unknown
- 1977-09-22 FR FR7728639A patent/FR2442848A1/fr active Pending
- 1977-09-22 GB GB39619/77A patent/GB1589237A/en not_active Expired
-
1978
- 1978-12-18 AR AR274489A patent/AR217886A1/es active
-
1979
- 1979-02-16 ES ES477799A patent/ES477799A1/es not_active Expired
- 1979-02-16 ES ES477800A patent/ES477800A1/es not_active Expired
Also Published As
Publication number | Publication date |
---|---|
AR218036A1 (es) | 1980-05-15 |
DK417377A (da) | 1978-03-23 |
AT360034B (de) | 1980-12-10 |
DE2741763A1 (de) | 1978-03-23 |
CA1080712A (fr) | 1980-07-01 |
LU78150A1 (fr) | 1978-01-23 |
ES477799A1 (es) | 1980-04-01 |
PT67067B (en) | 1979-02-19 |
NL7710389A (nl) | 1978-03-28 |
GB1589237A (en) | 1981-05-07 |
RO72226A (fr) | 1982-09-09 |
GR71699B (fr) | 1983-06-21 |
ES477800A1 (es) | 1979-10-16 |
FR2442848A1 (fr) | 1980-06-27 |
FI772802A (fi) | 1978-03-23 |
ES462543A1 (es) | 1979-06-16 |
AU513760B2 (en) | 1980-12-18 |
PT67067A (en) | 1977-10-01 |
BG29287A3 (en) | 1980-10-15 |
DD132586A5 (de) | 1978-10-11 |
AU2899577A (en) | 1979-03-29 |
AR217886A1 (es) | 1980-04-30 |
ATA677577A (de) | 1980-05-15 |
JPS5340798A (en) | 1978-04-13 |
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