GB1562943A - Pyrazole derivatives and their manufacture and use - Google Patents
Pyrazole derivatives and their manufacture and use Download PDFInfo
- Publication number
- GB1562943A GB1562943A GB33042/76A GB3304276A GB1562943A GB 1562943 A GB1562943 A GB 1562943A GB 33042/76 A GB33042/76 A GB 33042/76A GB 3304276 A GB3304276 A GB 3304276A GB 1562943 A GB1562943 A GB 1562943A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- group
- acid
- pyrazolylacetic
- compound
- 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
- 150000003217 pyrazoles Chemical class 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 238000002844 melting Methods 0.000 claims description 93
- 230000008018 melting Effects 0.000 claims description 93
- 150000001875 compounds Chemical class 0.000 claims description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 40
- 239000002253 acid Substances 0.000 claims description 30
- 239000011541 reaction mixture Substances 0.000 claims description 30
- -1 alkali metal salt Chemical class 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- 150000002825 nitriles Chemical class 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 10
- 125000004494 ethyl ester group Chemical group 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 6
- KXKJVHXKYVXBMK-UHFFFAOYSA-N 2-(1,4-diphenylpyrazol-3-yl)acetic acid Chemical compound OC(=O)CC1=NN(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 KXKJVHXKYVXBMK-UHFFFAOYSA-N 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- DNZYLNQLPCWZJZ-UHFFFAOYSA-N 3-(bromomethyl)-1,4-diphenylpyrazole Chemical compound BrCC1=NN(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 DNZYLNQLPCWZJZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000443 aerosol Substances 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- MLIREBYILWEBDM-UHFFFAOYSA-N anhydrous cyanoacetic acid Natural products OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002775 capsule Substances 0.000 claims description 4
- WOSXKSUCXLDVPX-UHFFFAOYSA-N ethyl 2-[chloro(phenyl)hydrazinylidene]acetate Chemical compound C(C)OC(C=NN(C1=CC=CC=C1)Cl)=O WOSXKSUCXLDVPX-UHFFFAOYSA-N 0.000 claims description 4
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims description 4
- 239000002674 ointment Substances 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- PKQVABNQYHJNBF-UHFFFAOYSA-N 2-(1,4-diphenylpyrazol-3-yl)acetamide Chemical compound NC(=O)CC1=NN(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 PKQVABNQYHJNBF-UHFFFAOYSA-N 0.000 claims description 3
- VPOVNCMVSKIXCD-UHFFFAOYSA-N 2-(1,4-diphenylpyrazol-3-yl)acetonitrile Chemical compound N#CCC1=NN(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 VPOVNCMVSKIXCD-UHFFFAOYSA-N 0.000 claims description 3
- URDMYVGHYFEOOU-UHFFFAOYSA-N 2-[1-(4-methylphenyl)-4-phenylpyrazol-3-yl]acetamide Chemical compound C1=CC(C)=CC=C1N1N=C(CC(N)=O)C(C=2C=CC=CC=2)=C1 URDMYVGHYFEOOU-UHFFFAOYSA-N 0.000 claims description 3
- YRTOFCREFRGYGI-UHFFFAOYSA-N 2-[4-(3-methoxyphenyl)-1-phenylpyrazol-3-yl]acetic acid Chemical compound COC1=CC=CC(C=2C(=NN(C=2)C=2C=CC=CC=2)CC(O)=O)=C1 YRTOFCREFRGYGI-UHFFFAOYSA-N 0.000 claims description 3
- WIKXEJHQDUYKQZ-UHFFFAOYSA-N 2-[4-(4-aminophenyl)-1-phenylpyrazol-3-yl]acetic acid Chemical compound C1=CC(N)=CC=C1C1=CN(C=2C=CC=CC=2)N=C1CC(O)=O WIKXEJHQDUYKQZ-UHFFFAOYSA-N 0.000 claims description 3
- CKRAGYYDQJEQTF-UHFFFAOYSA-N 3-methylbutyl 2-[4-(4-nitrophenyl)-1-phenylpyrazol-3-yl]acetate Chemical compound CC(C)CCOC(=O)CC1=NN(C=2C=CC=CC=2)C=C1C1=CC=C([N+]([O-])=O)C=C1 CKRAGYYDQJEQTF-UHFFFAOYSA-N 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 239000007868 Raney catalyst Substances 0.000 claims description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 3
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 239000001569 carbon dioxide Substances 0.000 claims description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 2
- COTPSEFOMUXLAK-UHFFFAOYSA-N 2-[1-(2-fluorophenyl)-4-phenylpyrazol-3-yl]acetic acid Chemical compound OC(=O)CC1=NN(C=2C(=CC=CC=2)F)C=C1C1=CC=CC=C1 COTPSEFOMUXLAK-UHFFFAOYSA-N 0.000 claims description 2
- JRMBGQWZIYZBIO-UHFFFAOYSA-N 2-[1-(2-methylphenyl)-4-phenylpyrazol-3-yl]acetic acid Chemical compound CC1=CC=CC=C1N1N=C(CC(O)=O)C(C=2C=CC=CC=2)=C1 JRMBGQWZIYZBIO-UHFFFAOYSA-N 0.000 claims description 2
- XOZQXGIZSIWBCR-UHFFFAOYSA-N 2-[1-(3-chloro-4-fluorophenyl)-4-phenylpyrazol-3-yl]acetic acid Chemical compound OC(=O)CC1=NN(C=2C=C(Cl)C(F)=CC=2)C=C1C1=CC=CC=C1 XOZQXGIZSIWBCR-UHFFFAOYSA-N 0.000 claims description 2
- JQZFNSFLABDVBX-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)-4-phenylpyrazol-3-yl]acetic acid Chemical compound OC(=O)CC1=NN(C=2C=CC(Cl)=CC=2)C=C1C1=CC=CC=C1 JQZFNSFLABDVBX-UHFFFAOYSA-N 0.000 claims description 2
- IURAJQHBCIOEGE-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)-4-(4-methoxyphenyl)pyrazol-3-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=CN(C=2C=CC(F)=CC=2)N=C1CC(O)=O IURAJQHBCIOEGE-UHFFFAOYSA-N 0.000 claims description 2
- FILXXDANKCYMKH-UHFFFAOYSA-N 2-[1-(4-methylphenyl)-4-phenylpyrazol-3-yl]acetic acid Chemical compound C1=CC(C)=CC=C1N1N=C(CC(O)=O)C(C=2C=CC=CC=2)=C1 FILXXDANKCYMKH-UHFFFAOYSA-N 0.000 claims description 2
- OQDYUMGIDGLHAK-UHFFFAOYSA-N 2-[4-(4-nitrophenyl)-1-phenylpyrazol-3-yl]acetic acid Chemical compound OC(=O)CC1=NN(C=2C=CC=CC=2)C=C1C1=CC=C([N+]([O-])=O)C=C1 OQDYUMGIDGLHAK-UHFFFAOYSA-N 0.000 claims description 2
- SYBNULNADTWVSX-UHFFFAOYSA-N 3-(1,4-diphenylpyrazol-3-yl)propanoic acid Chemical compound OC(=O)CCC1=NN(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 SYBNULNADTWVSX-UHFFFAOYSA-N 0.000 claims description 2
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 150000001879 copper Chemical class 0.000 claims description 2
- XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- VVERUMZUZIFIQN-ZROIWOOFSA-N ethyl (2z)-2-chloro-2-[(4-fluorophenyl)hydrazinylidene]acetate Chemical compound CCOC(=O)C(\Cl)=N\NC1=CC=C(F)C=C1 VVERUMZUZIFIQN-ZROIWOOFSA-N 0.000 claims description 2
- OFEUHILZGTTZAU-UHFFFAOYSA-N ethyl 2-[1-(4-methylphenyl)-4-phenylpyrazol-3-yl]acetate Chemical compound CCOC(=O)CC1=NN(C=2C=CC(C)=CC=2)C=C1C1=CC=CC=C1 OFEUHILZGTTZAU-UHFFFAOYSA-N 0.000 claims description 2
- PNAXSVDCKPIQLL-UHFFFAOYSA-N ethyl 4-(4-aminophenyl)-1-(4-fluorophenyl)pyrazole-3-carboxylate Chemical compound CCOC(=O)C1=NN(C=2C=CC(F)=CC=2)C=C1C1=CC=C(N)C=C1 PNAXSVDCKPIQLL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- CLDWGXZGFUNWKB-UHFFFAOYSA-M silver;benzoate Chemical compound [Ag+].[O-]C(=O)C1=CC=CC=C1 CLDWGXZGFUNWKB-UHFFFAOYSA-M 0.000 claims description 2
- QRTVRLWLZTYQQO-UHFFFAOYSA-M sodium;3-(1,4-diphenylpyrazol-3-yl)propanoate Chemical compound [Na+].[O-]C(=O)CCC1=NN(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 QRTVRLWLZTYQQO-UHFFFAOYSA-M 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- 230000000875 corresponding effect Effects 0.000 claims 2
- IGBOXGVHHSLXPE-UHFFFAOYSA-N 2-(1h-pyrazol-5-yl)acetonitrile Chemical compound N#CCC=1C=CNN=1 IGBOXGVHHSLXPE-UHFFFAOYSA-N 0.000 claims 1
- ZUDUZUHCRRTSEX-UHFFFAOYSA-N 2-[1-(2-fluorophenyl)-4-phenylpyrazol-3-yl]acetonitrile Chemical compound FC1=CC=CC=C1N1N=C(CC#N)C(C=2C=CC=CC=2)=C1 ZUDUZUHCRRTSEX-UHFFFAOYSA-N 0.000 claims 1
- YXDHQAZLISFKIB-UHFFFAOYSA-N 2-[1-(4-methylphenyl)-4-phenylpyrazol-3-yl]acetonitrile Chemical compound C1=CC(C)=CC=C1N1N=C(CC#N)C(C=2C=CC=CC=2)=C1 YXDHQAZLISFKIB-UHFFFAOYSA-N 0.000 claims 1
- WMJZPMJTHUVWSW-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-1-phenylpyrazol-3-yl]acetic acid Chemical compound OC(=O)CC1=NN(C=2C=CC=CC=2)C=C1C1=CC=C(Cl)C=C1 WMJZPMJTHUVWSW-UHFFFAOYSA-N 0.000 claims 1
- XSBXXGTYBGVWFE-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-1-phenylpyrazol-3-yl]acetonitrile Chemical compound C1=CC(Cl)=CC=C1C1=CN(C=2C=CC=CC=2)N=C1CC#N XSBXXGTYBGVWFE-UHFFFAOYSA-N 0.000 claims 1
- JNPOKJPHLJXFMP-UHFFFAOYSA-N 2-[4-(4-methoxyphenyl)-1-phenylpyrazol-3-yl]acetonitrile Chemical compound C1=CC(OC)=CC=C1C1=CN(C=2C=CC=CC=2)N=C1CC#N JNPOKJPHLJXFMP-UHFFFAOYSA-N 0.000 claims 1
- CSERFIBDMLKTDO-UHFFFAOYSA-N 2-[4-phenyl-1-[4-(trifluoromethyl)phenyl]pyrazol-3-yl]acetic acid Chemical compound OC(=O)CC1=NN(C=2C=CC(=CC=2)C(F)(F)F)C=C1C1=CC=CC=C1 CSERFIBDMLKTDO-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
- 239000008298 dragée Substances 0.000 claims 1
- RWYKRIUYFOKIOP-UHFFFAOYSA-N ethyl 3-(1,4-diphenylpyrazol-3-yl)propanoate Chemical compound CCOC(=O)CCC1=NN(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 RWYKRIUYFOKIOP-UHFFFAOYSA-N 0.000 claims 1
- GASCHJCKOCMANU-UHFFFAOYSA-N ethyl 4-(1,4-diphenylpyrazol-3-yl)butanoate Chemical compound CCOC(=O)CCCC1=NN(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 GASCHJCKOCMANU-UHFFFAOYSA-N 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000012043 crude product Substances 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000013067 intermediate product Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 235000017550 sodium carbonate Nutrition 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000001117 sulphuric acid Substances 0.000 description 4
- 235000011149 sulphuric acid Nutrition 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- LEWDRFAKTLEBBM-UHFFFAOYSA-N ethyl 4-(4-aminophenyl)-1-phenylpyrazole-3-carboxylate Chemical compound CCOC(=O)C1=NN(C=2C=CC=CC=2)C=C1C1=CC=C(N)C=C1 LEWDRFAKTLEBBM-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 3
- 229910001923 silver oxide Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
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- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- LTPRVINQSYJPIR-NTEUORMPSA-N ethyl (2e)-2-chloro-2-[(2-chlorophenyl)hydrazinylidene]acetate Chemical compound CCOC(=O)C(\Cl)=N/NC1=CC=CC=C1Cl LTPRVINQSYJPIR-NTEUORMPSA-N 0.000 description 1
- DDJOIKUARWSPEQ-NTEUORMPSA-N ethyl (2e)-2-chloro-2-[(4-chlorophenyl)hydrazinylidene]acetate Chemical compound CCOC(=O)C(\Cl)=N/NC1=CC=C(Cl)C=C1 DDJOIKUARWSPEQ-NTEUORMPSA-N 0.000 description 1
- QNDYBLUTYVPPCI-UHFFFAOYSA-N ethyl 1,4-diphenylpyrazole-3-carboxylate Chemical compound CCOC(=O)C1=NN(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 QNDYBLUTYVPPCI-UHFFFAOYSA-N 0.000 description 1
- AJLJCSCXCNVCSQ-UHFFFAOYSA-N ethyl 1-(2-chlorophenyl)-4-phenylpyrazole-3-carboxylate Chemical compound CCOC(=O)C1=NN(C=2C(=CC=CC=2)Cl)C=C1C1=CC=CC=C1 AJLJCSCXCNVCSQ-UHFFFAOYSA-N 0.000 description 1
- RNOXVRLHCKCUON-UHFFFAOYSA-N ethyl 1-(2-methylphenyl)-4-phenylpyrazole-3-carboxylate Chemical compound CCOC(=O)C1=NN(C=2C(=CC=CC=2)C)C=C1C1=CC=CC=C1 RNOXVRLHCKCUON-UHFFFAOYSA-N 0.000 description 1
- RGNCKAOBXWIRII-UHFFFAOYSA-N ethyl 1-(3-fluorophenyl)-4-phenylpyrazole-3-carboxylate Chemical compound CCOC(=O)C1=NN(C=2C=C(F)C=CC=2)C=C1C1=CC=CC=C1 RGNCKAOBXWIRII-UHFFFAOYSA-N 0.000 description 1
- FFWCAMHWLQVUDW-UHFFFAOYSA-N ethyl 1-(4-fluorophenyl)-4-phenylpyrazole-3-carboxylate Chemical compound CCOC(=O)C1=NN(C=2C=CC(F)=CC=2)C=C1C1=CC=CC=C1 FFWCAMHWLQVUDW-UHFFFAOYSA-N 0.000 description 1
- RKCBIDVROMTGHF-UHFFFAOYSA-N ethyl 2-[(2-methylphenyl)hydrazinylidene]-4-morpholin-4-yl-3-phenylbut-3-enoate Chemical compound C1COCCN1C=C(C=1C=CC=CC=1)C(C(=O)OCC)=NNC1=CC=CC=C1C RKCBIDVROMTGHF-UHFFFAOYSA-N 0.000 description 1
- LAZFQMISVZTABK-UHFFFAOYSA-N ethyl 2-[(3,4-dichlorophenyl)hydrazinylidene]-4-morpholin-4-yl-3-phenylbut-3-enoate Chemical compound C(C)OC(C(C(C1=CC=CC=C1)=CN1CCOCC1)=NNC1=CC(=C(C=C1)Cl)Cl)=O LAZFQMISVZTABK-UHFFFAOYSA-N 0.000 description 1
- DQWDPPNSABWTEM-UHFFFAOYSA-N ethyl 2-[(4-chlorophenyl)hydrazinylidene]-4-morpholin-4-yl-3-phenylbut-3-enoate Chemical compound C(C)OC(C(C(C1=CC=CC=C1)=CN1CCOCC1)=NNC1=CC=C(C=C1)Cl)=O DQWDPPNSABWTEM-UHFFFAOYSA-N 0.000 description 1
- BOZFDJPSLATPSQ-UHFFFAOYSA-N ethyl 2-[(4-fluorophenyl)hydrazinylidene]-4-morpholin-4-yl-3-phenylbut-3-enoate Chemical compound C(C)OC(C(C(C1=CC=CC=C1)=CN1CCOCC1)=NNC1=CC=C(C=C1)F)=O BOZFDJPSLATPSQ-UHFFFAOYSA-N 0.000 description 1
- FLFRMUNZZFVJRG-UHFFFAOYSA-N ethyl 2-[(4-methylphenyl)hydrazinylidene]-4-morpholin-4-yl-3-phenylbut-3-enoate Chemical compound C1COCCN1C=C(C=1C=CC=CC=1)C(C(=O)OCC)=NNC1=CC=C(C)C=C1 FLFRMUNZZFVJRG-UHFFFAOYSA-N 0.000 description 1
- CJTBOQSRJXKXAA-UHFFFAOYSA-N ethyl 2-chloro-2-[(2-fluorophenyl)hydrazinylidene]acetate Chemical compound CCOC(=O)C(Cl)=NNC1=CC=CC=C1F CJTBOQSRJXKXAA-UHFFFAOYSA-N 0.000 description 1
- JHOCJALLQHWBON-UHFFFAOYSA-N ethyl 2-chloro-2-[(2-methylphenyl)hydrazinylidene]acetate Chemical compound CCOC(=O)C(Cl)=NNC1=CC=CC=C1C JHOCJALLQHWBON-UHFFFAOYSA-N 0.000 description 1
- XQMSUQFIHSSTAP-UHFFFAOYSA-N ethyl 2-chloro-2-[(3-fluorophenyl)hydrazinylidene]acetate Chemical compound CCOC(=O)C(Cl)=NNC1=CC=CC(F)=C1 XQMSUQFIHSSTAP-UHFFFAOYSA-N 0.000 description 1
- VVERUMZUZIFIQN-UHFFFAOYSA-N ethyl 2-chloro-2-[(4-fluorophenyl)hydrazinylidene]acetate Chemical compound CCOC(=O)C(Cl)=NNC1=CC=C(F)C=C1 VVERUMZUZIFIQN-UHFFFAOYSA-N 0.000 description 1
- RDULEYWUGKOCMR-UHFFFAOYSA-N ethyl 2-chloro-3-oxobutanoate Chemical compound CCOC(=O)C(Cl)C(C)=O RDULEYWUGKOCMR-UHFFFAOYSA-N 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- RVGVMZSUUBQBPA-UHFFFAOYSA-N ethyl 4-(4-chlorophenyl)-1-phenylpyrazole-3-carboxylate Chemical compound CCOC(=O)C1=NN(C=2C=CC=CC=2)C=C1C1=CC=C(Cl)C=C1 RVGVMZSUUBQBPA-UHFFFAOYSA-N 0.000 description 1
- QRQSPFMXJCVACO-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)-1-phenylpyrazole-3-carboxylate Chemical compound CCOC(=O)C1=NN(C=2C=CC=CC=2)C=C1C1=CC=C(OC)C=C1 QRQSPFMXJCVACO-UHFFFAOYSA-N 0.000 description 1
- UGPQCWPSCIGLLY-UHFFFAOYSA-N ethyl 4-(dimethylamino)-3-(4-nitrophenyl)-2-(phenylhydrazinylidene)but-3-enoate Chemical compound C(C)OC(C(C(C1=CC=C(C=C1)[N+](=O)[O-])=CN(C)C)=NNC1=CC=CC=C1)=O UGPQCWPSCIGLLY-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 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
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- MGNPLIACIXIYJE-UHFFFAOYSA-N n-fluoroaniline Chemical compound FNC1=CC=CC=C1 MGNPLIACIXIYJE-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 201000004700 rosacea Diseases 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 210000003934 vacuole Anatomy 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or 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
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2536003A DE2536003C2 (de) | 1975-08-08 | 1975-08-08 | Pyrazol-Derivate, ihre Herstellung und diese enthaltende pharmazeutische Derivate |
| DE19762633992 DE2633992A1 (de) | 1975-08-08 | 1976-07-26 | Neue pyrazol-derivate, ihre herstellung und verwendung |
| AU22014/77A AU514889B2 (en) | 1975-08-08 | 1977-02-07 | Pyrazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1562943A true GB1562943A (en) | 1980-03-19 |
Family
ID=40520846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB33042/76A Expired GB1562943A (en) | 1975-08-08 | 1976-08-09 | Pyrazole derivatives and their manufacture and use |
Country Status (11)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3203307A1 (de) * | 1982-01-27 | 1983-07-28 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Phosphonate, und diese enthaltende pharmazeutische verbindungen |
| US4826868A (en) * | 1986-05-29 | 1989-05-02 | Ortho Pharmaceutical Corporation | 1,5-Diaryl-3-substituted pyrazoles pharmaceutical compositions and use |
| AU611437B2 (en) * | 1987-05-29 | 1991-06-13 | Ortho Pharmaceutical Corporation | Pharmacologically active 2- and 3-substituted (1',5'-diaryl-3-pyrazolyl)-n-hydroxypropanamides and method for synthesizing the same |
| IT1226387B (it) * | 1988-07-08 | 1991-01-15 | Seuref Ag | Processo per la preparazione di acidi 1,4-diaril-3-pirazol-acetici |
| CN102186809A (zh) * | 2008-08-14 | 2011-09-14 | 拜尔农作物科学股份公司 | 杀虫性的4-苯基-1h-吡唑 |
| CN103929964A (zh) | 2011-09-23 | 2014-07-16 | 拜耳知识产权有限责任公司 | 4-取代的1-苯基吡唑-3-甲酸衍生物作为对抗非生物植物胁迫的活性物质的用途 |
| US9611263B2 (en) | 2013-10-08 | 2017-04-04 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE755924A (fr) * | 1969-09-12 | 1971-02-15 | Byk Gulden Lomberg Chem Fab | Derives d'acide pyrazole-4-acetique, leur procede de preparation et medicaments en contenant |
| DE2347015C2 (de) * | 1973-09-14 | 1985-12-12 | Schering AG, 1000 Berlin und 4709 Bergkamen | Neue Pyrazolyloxyessigsäurederivate, Verfahren zu ihrer Herstellung und diese enthaltende Mittel |
-
1976
- 1976-07-26 DE DE19762633992 patent/DE2633992A1/de active Granted
- 1976-08-06 BE BE169630A patent/BE844972A/xx not_active IP Right Cessation
- 1976-08-06 NL NLAANVRAGE7608810,A patent/NL188696C/xx not_active IP Right Cessation
- 1976-08-06 DK DK356676A patent/DK147973C/da not_active IP Right Cessation
- 1976-08-06 LU LU75548A patent/LU75548A1/xx unknown
- 1976-08-09 GB GB33042/76A patent/GB1562943A/en not_active Expired
- 1976-08-09 IE IE1758/76A patent/IE43659B1/en not_active IP Right Cessation
-
1977
- 1977-01-12 DD DD7700196901A patent/DD128130A5/xx not_active IP Right Cessation
- 1977-01-14 HU HU77SCHE592A patent/HU175423B/hu not_active IP Right Cessation
- 1977-02-07 CS CS773720A patent/CS216206B2/cs unknown
- 1977-02-07 CS CS77787A patent/CS216205B2/cs unknown
- 1977-02-07 AU AU22014/77A patent/AU514889B2/en not_active Expired
-
1979
- 1979-05-30 CS CS793721A patent/CS216207B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK147973C (da) | 1985-07-08 |
| BE844972A (fr) | 1977-02-07 |
| AU2201477A (en) | 1978-08-17 |
| DK147973B (da) | 1985-01-21 |
| LU75548A1 (enrdf_load_stackoverflow) | 1977-03-25 |
| DD128130A5 (de) | 1977-11-02 |
| DE2633992C2 (enrdf_load_stackoverflow) | 1988-04-28 |
| DK356676A (da) | 1977-02-09 |
| NL7608810A (nl) | 1977-02-10 |
| HU175423B (hu) | 1980-07-28 |
| NL188696C (nl) | 1992-09-01 |
| IE43659L (en) | 1977-02-08 |
| CS216207B2 (en) | 1982-10-29 |
| DE2633992A1 (de) | 1978-02-09 |
| NL188696B (nl) | 1992-04-01 |
| CS216205B2 (en) | 1982-10-29 |
| AU514889B2 (en) | 1981-03-05 |
| CS216206B2 (en) | 1982-10-29 |
| IE43659B1 (en) | 1981-04-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19950809 |