CS216205B2 - Method of making the derivatives of the 1,4-diphenylpyrazole - Google Patents
Method of making the derivatives of the 1,4-diphenylpyrazole Download PDFInfo
- Publication number
- CS216205B2 CS216205B2 CS77787A CS78777A CS216205B2 CS 216205 B2 CS216205 B2 CS 216205B2 CS 77787 A CS77787 A CS 77787A CS 78777 A CS78777 A CS 78777A CS 216205 B2 CS216205 B2 CS 216205B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- phenyl
- acid
- ethyl ester
- concentrated
- vacuo
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 8
- CYKVEARUNZRABH-UHFFFAOYSA-N 1,4-diphenylpyrazole Chemical compound C1=NN(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 CYKVEARUNZRABH-UHFFFAOYSA-N 0.000 title description 2
- -1 alkali metal cyanide Chemical class 0.000 claims abstract description 29
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 150000002825 nitriles Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 11
- 150000001735 carboxylic acids Chemical class 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 12
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- 239000003054 catalyst Substances 0.000 abstract description 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract description 3
- 125000005843 halogen group Chemical group 0.000 abstract description 2
- 230000007062 hydrolysis Effects 0.000 abstract description 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 2
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 208000018556 stomach disease Diseases 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- 239000002253 acid Substances 0.000 description 26
- 239000000243 solution Substances 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 235000002639 sodium chloride Nutrition 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 11
- 150000007513 acids Chemical class 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- 125000004494 ethyl ester group Chemical group 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 206010030113 Oedema Diseases 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 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 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 210000002683 foot Anatomy 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003217 pyrazoles Chemical class 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 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 description 3
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 150000002148 esters 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
- 238000011156 evaluation Methods 0.000 description 3
- 210000000548 hind-foot Anatomy 0.000 description 3
- 230000001939 inductive effect Effects 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 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
- 239000011780 sodium chloride Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 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 description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
- 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 description 2
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 201000009053 Neurodermatitis Diseases 0.000 description 2
- 206010036030 Polyarthritis Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000700157 Rattus norvegicus Species 0.000 description 2
- 208000007107 Stomach Ulcer Diseases 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ADOGROGGCKESLH-UHFFFAOYSA-N ethyl 1-(4-methylphenyl)-4-phenylpyrazole-3-carboxylate Chemical compound CCOC(=O)C1=NN(C=2C=CC(C)=CC=2)C=C1C1=CC=CC=C1 ADOGROGGCKESLH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000002496 gastric effect Effects 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
- 238000005259 measurement Methods 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- BJHKTGBBMIKJLI-UHFFFAOYSA-N (1,4-diphenylpyrazol-3-yl)methanol Chemical compound OCC1=NN(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 BJHKTGBBMIKJLI-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- WRQUNZOBPUNVCX-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)-4-phenylpyrazol-3-yl]acetic acid Chemical compound OC(=O)CC1=NN(C=2C=CC(F)=CC=2)C=C1C1=CC=CC=C1 WRQUNZOBPUNVCX-UHFFFAOYSA-N 0.000 description 1
- 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 description 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 description 1
- FTZQXOJYPFINKJ-UHFFFAOYSA-N 2-fluoroaniline Chemical compound NC1=CC=CC=C1F FTZQXOJYPFINKJ-UHFFFAOYSA-N 0.000 description 1
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 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 description 1
- VUWBFEYSOONJRC-UHFFFAOYSA-N 3-(4-chlorophenyl)-4-methyl-1h-pyrazole-5-carboxylic acid Chemical compound CC1=C(C(O)=O)NN=C1C1=CC=C(Cl)C=C1 VUWBFEYSOONJRC-UHFFFAOYSA-N 0.000 description 1
- NPSAOSSFAVJWMD-UHFFFAOYSA-N 3-(bromomethyl)-1-(3-fluorophenyl)-4-phenylpyrazole Chemical compound FC1=CC=CC(N2N=C(CBr)C(=C2)C=2C=CC=CC=2)=C1 NPSAOSSFAVJWMD-UHFFFAOYSA-N 0.000 description 1
- PMBNSTCZHRWXDK-UHFFFAOYSA-N 3-(bromomethyl)-1-(4-fluorophenyl)-4-phenylpyrazole Chemical compound C1=CC(F)=CC=C1N1N=C(CBr)C(C=2C=CC=CC=2)=C1 PMBNSTCZHRWXDK-UHFFFAOYSA-N 0.000 description 1
- XMMABLUUSNBNOF-UHFFFAOYSA-N 3-(bromomethyl)-1-(4-methylphenyl)-4-phenylpyrazole Chemical compound C1=CC(C)=CC=C1N1N=C(CBr)C(C=2C=CC=CC=2)=C1 XMMABLUUSNBNOF-UHFFFAOYSA-N 0.000 description 1
- QVHCMCZPYKSZTO-UHFFFAOYSA-N 3-(chloromethyl)-4-(4-methoxyphenyl)-1-phenylpyrazole Chemical compound C1=CC(OC)=CC=C1C1=CN(C=2C=CC=CC=2)N=C1CCl QVHCMCZPYKSZTO-UHFFFAOYSA-N 0.000 description 1
- QZVQQUVWFIZUBQ-UHFFFAOYSA-N 3-fluoroaniline Chemical compound NC1=CC=CC(F)=C1 QZVQQUVWFIZUBQ-UHFFFAOYSA-N 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- GNCPEYHWRLOUID-UHFFFAOYSA-N 4-(1,4-diphenylpyrazol-3-yl)butanoic acid Chemical compound OC(=O)CCCC1=NN(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 GNCPEYHWRLOUID-UHFFFAOYSA-N 0.000 description 1
- DRLPQHUSIRTYBM-UHFFFAOYSA-N 4-(1-phenylethenyl)morpholine Chemical compound C=1C=CC=CC=1C(=C)N1CCOCC1 DRLPQHUSIRTYBM-UHFFFAOYSA-N 0.000 description 1
- WOPXPLSSEMQCLL-UHFFFAOYSA-N 4-(4-chlorophenyl)-1-phenylpyrazole-3-carboxylic acid Chemical compound OC(=O)C1=NN(C=2C=CC=CC=2)C=C1C1=CC=C(Cl)C=C1 WOPXPLSSEMQCLL-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- ITDKGJIKBWSABM-UHFFFAOYSA-M 4-methylbenzenediazonium;chloride Chemical compound [Cl-].CC1=CC=C([N+]#N)C=C1 ITDKGJIKBWSABM-UHFFFAOYSA-M 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 229920000856 Amylose Polymers 0.000 description 1
- 241000209200 Bromus Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 208000009386 Experimental Arthritis Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010064000 Lichenoid keratosis Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 208000008350 Pruritus Vulvae Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 241001303601 Rosacea Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 206010056530 Vulvovaginal pruritus Diseases 0.000 description 1
- AEAAPRWWGCHQQZ-UHFFFAOYSA-N [1-(2-fluorophenyl)-4-phenylpyrazol-3-yl]methanol Chemical compound OCC1=NN(C=2C(=CC=CC=2)F)C=C1C1=CC=CC=C1 AEAAPRWWGCHQQZ-UHFFFAOYSA-N 0.000 description 1
- RQTRPHFIPVQJHA-UHFFFAOYSA-N [1-(3-fluorophenyl)-4-phenylpyrazol-3-yl]methanol Chemical compound OCC1=NN(C=2C=C(F)C=CC=2)C=C1C1=CC=CC=C1 RQTRPHFIPVQJHA-UHFFFAOYSA-N 0.000 description 1
- JNMNPILBXCITOV-UHFFFAOYSA-N [1-(4-chlorophenyl)-4-phenylpyrazol-3-yl]methanol Chemical compound OCC1=NN(C=2C=CC(Cl)=CC=2)C=C1C1=CC=CC=C1 JNMNPILBXCITOV-UHFFFAOYSA-N 0.000 description 1
- CZGXKIWHPNPOPB-UHFFFAOYSA-N [1-(4-fluorophenyl)-4-phenylpyrazol-3-yl]methanol Chemical compound OCC1=NN(C=2C=CC(F)=CC=2)C=C1C1=CC=CC=C1 CZGXKIWHPNPOPB-UHFFFAOYSA-N 0.000 description 1
- YISIZVPTQIWUJZ-UHFFFAOYSA-N [1-(4-methylphenyl)-4-phenylpyrazol-3-yl]methanol Chemical compound C1=CC(C)=CC=C1N1N=C(CO)C(C=2C=CC=CC=2)=C1 YISIZVPTQIWUJZ-UHFFFAOYSA-N 0.000 description 1
- DEXSTOXKQPIGOQ-UHFFFAOYSA-N [4-(4-chlorophenyl)-1-phenylpyrazol-3-yl]methanol Chemical compound OCC1=NN(C=2C=CC=CC=2)C=C1C1=CC=C(Cl)C=C1 DEXSTOXKQPIGOQ-UHFFFAOYSA-N 0.000 description 1
- RUJGMOUMONYMEC-UHFFFAOYSA-N [4-(4-methoxyphenyl)-1-phenylpyrazol-3-yl]methanol Chemical compound C1=CC(OC)=CC=C1C1=CN(C=2C=CC=CC=2)N=C1CO RUJGMOUMONYMEC-UHFFFAOYSA-N 0.000 description 1
- JFQKNBNHEGNFEH-UHFFFAOYSA-N [4-phenyl-1-[3-(trifluoromethyl)phenyl]pyrazol-3-yl]methanol Chemical compound OCC1=NN(C=2C=C(C=CC=2)C(F)(F)F)C=C1C1=CC=CC=C1 JFQKNBNHEGNFEH-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 208000026816 acute arthritis Diseases 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 238000011861 anti-inflammatory therapy Methods 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- GLNADSQYFUSGOU-UHFFFAOYSA-J chembl1640 Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(N=NC3=CC=C(C=C3C)C=3C=C(C(=CC=3)N=NC=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)C)=C(O)C2=C1N GLNADSQYFUSGOU-UHFFFAOYSA-J 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
- 229940112669 cuprous oxide Drugs 0.000 description 1
- WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 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 description 1
- GPUAZRANRJWSPM-UHFFFAOYSA-N ethyl 1-(2-fluorophenyl)-4-phenylpyrazole-3-carboxylate Chemical compound CCOC(=O)C1=NN(C=2C(=CC=CC=2)F)C=C1C1=CC=CC=C1 GPUAZRANRJWSPM-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
- IZJHYJDZIJLTOD-UHFFFAOYSA-N ethyl 2-chloro-2-[(4-methylphenyl)hydrazinylidene]acetate Chemical compound CCOC(=O)C(Cl)=NNC1=CC=C(C)C=C1 IZJHYJDZIJLTOD-UHFFFAOYSA-N 0.000 description 1
- HXRVSIPGGUOVJA-UHFFFAOYSA-N ethyl 2-chloro-2-[[3-(trifluoromethyl)phenyl]hydrazinylidene]acetate Chemical compound CCOC(=O)C(Cl)=NNC1=CC=CC(C(F)(F)F)=C1 HXRVSIPGGUOVJA-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
- HAWMBAQHMKMRSO-UHFFFAOYSA-N ethyl 4-morpholin-4-yl-3-phenyl-2-(phenylhydrazinylidene)but-3-enoate Chemical compound C(C)OC(C(C(=CN1CCOCC1)C1=CC=CC=C1)=NNC1=CC=CC=C1)=O HAWMBAQHMKMRSO-UHFFFAOYSA-N 0.000 description 1
- GWUMGJCJIJTFDG-UHFFFAOYSA-N ethyl 4-phenyl-1-[3-(trifluoromethyl)phenyl]pyrazole-3-carboxylate Chemical compound CCOC(=O)C1=NN(C=2C=C(C=CC=2)C(F)(F)F)C=C1C1=CC=CC=C1 GWUMGJCJIJTFDG-UHFFFAOYSA-N 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 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
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 201000011486 lichen planus Diseases 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 208000030428 polyarticular arthritis Diseases 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 201000004700 rosacea Diseases 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ORTCURDWAOEPHC-UHFFFAOYSA-M sodium 2-(1,4-diphenylpyrazol-3-yl)acetate Chemical compound [Na+].[O-]C(=O)CC1=NN(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 ORTCURDWAOEPHC-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 210000002784 stomach Anatomy 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
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 229940005605 valeric acid Drugs 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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (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)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS77787A CS216205B2 (en) | 1975-08-08 | 1977-02-07 | Method of making the derivatives of the 1,4-diphenylpyrazole |
| CS793721A CS216207B2 (en) | 1975-08-08 | 1979-05-30 | Method of making the derivatives of the 1,4-diphenylpyrazole |
Applications Claiming Priority (4)
| 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 |
| CS77787A CS216205B2 (en) | 1975-08-08 | 1977-02-07 | Method of making the derivatives of the 1,4-diphenylpyrazole |
| AU22014/77A AU514889B2 (en) | 1975-08-08 | 1977-02-07 | Pyrazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS216205B2 true CS216205B2 (en) | 1982-10-29 |
Family
ID=40520846
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS77787A CS216205B2 (en) | 1975-08-08 | 1977-02-07 | Method of making the derivatives of the 1,4-diphenylpyrazole |
| CS773720A CS216206B2 (en) | 1975-08-08 | 1977-02-07 | Method of making the derivatives of the diphenylpyrazole |
| CS793721A CS216207B2 (en) | 1975-08-08 | 1979-05-30 | Method of making the derivatives of the 1,4-diphenylpyrazole |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS773720A CS216206B2 (en) | 1975-08-08 | 1977-02-07 | Method of making the derivatives of the diphenylpyrazole |
| CS793721A CS216207B2 (en) | 1975-08-08 | 1979-05-30 | Method of making the derivatives of the 1,4-diphenylpyrazole |
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 |
| AU2009281457A1 (en) * | 2008-08-14 | 2010-02-18 | Bayer Cropscience Ag | Insecticidal 4-phenyl-1H-pyrazoles |
| 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 |
| WO2015054283A1 (en) * | 2013-10-08 | 2015-04-16 | 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 DK DK356676A patent/DK147973C/da not_active IP Right Cessation
- 1976-08-06 BE BE169630A patent/BE844972A/xx not_active IP Right Cessation
- 1976-08-06 LU LU75548A patent/LU75548A1/xx unknown
- 1976-08-06 NL NLAANVRAGE7608810,A patent/NL188696C/xx not_active IP Right Cessation
- 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 CS77787A patent/CS216205B2/cs unknown
- 1977-02-07 AU AU22014/77A patent/AU514889B2/en not_active Expired
- 1977-02-07 CS CS773720A patent/CS216206B2/cs unknown
-
1979
- 1979-05-30 CS CS793721A patent/CS216207B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2201477A (en) | 1978-08-17 |
| HU175423B (hu) | 1980-07-28 |
| DK147973B (da) | 1985-01-21 |
| AU514889B2 (en) | 1981-03-05 |
| DK147973C (da) | 1985-07-08 |
| GB1562943A (en) | 1980-03-19 |
| BE844972A (fr) | 1977-02-07 |
| CS216207B2 (en) | 1982-10-29 |
| LU75548A1 (enrdf_load_stackoverflow) | 1977-03-25 |
| NL188696B (nl) | 1992-04-01 |
| DK356676A (da) | 1977-02-09 |
| IE43659L (en) | 1977-02-08 |
| IE43659B1 (en) | 1981-04-22 |
| NL7608810A (nl) | 1977-02-10 |
| NL188696C (nl) | 1992-09-01 |
| DE2633992C2 (enrdf_load_stackoverflow) | 1988-04-28 |
| DE2633992A1 (de) | 1978-02-09 |
| DD128130A5 (de) | 1977-11-02 |
| CS216206B2 (en) | 1982-10-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4490371A (en) | N,N-Disubstituted-(2-oxo-1,2,3,5-tetrahydroimidazo-[2,1-B]quinazolinyl)oxyalkylamides | |
| US4110337A (en) | Triazolobenzodiazepines | |
| US4621089A (en) | Pyrazolopyridine derivatives and their use in treating inflammation and allergic conditions | |
| JPH0133470B2 (enrdf_load_stackoverflow) | ||
| US4670432A (en) | Pyrazolopyridine derivatives useful in treating inflammation and allergic conditions | |
| JP3122792B2 (ja) | 新規な活性化合物 | |
| US4239901A (en) | Pyrazol-1-ylphenylacetic acids | |
| CS216205B2 (en) | Method of making the derivatives of the 1,4-diphenylpyrazole | |
| US3468939A (en) | 4- and 5-aryl-1-naphthaleneacetic acid compounds | |
| US4472433A (en) | Phenoxyphenyl acetic acids and their medicinal use | |
| US4325964A (en) | Phenylamidine derivatives | |
| JPS6037099B2 (ja) | 新規ピラゾ−ル誘導体及びその製造法 | |
| JPH03190872A (ja) | 新規なチオフェン誘導体 | |
| JP2939280B2 (ja) | フッ素置換メトキシキノロンカルボン酸誘導体 | |
| JPH10512579A (ja) | 新規の９Ｈ−ピリド［３，４−ｂ］インドール−誘導体 | |
| DE3872576T2 (de) | Leukotrienantagonisten. | |
| US3974176A (en) | Halogen pyrazoles derivatives, a method for producing these halogen pyrazole derivatives and medicaments containing them | |
| US4243665A (en) | 2-Heterocyclylalkyl-6-methoxy-naphthalenes | |
| US4624949A (en) | Dibenzo[b,d]thiopyran derivatives, pharmaceutical composition and use | |
| SU873871A3 (ru) | Способ получени производных фенилуксусной кислоты | |
| JPS62149672A (ja) | ４Ｈ−ベンゾ〔４，５〕シクロヘプタ〔１，２−ｂ〕チオフエン誘導体 | |
| JPS59186962A (ja) | イミダゾリン誘導体およびそれを含有する医薬 | |
| IL34468A (en) | Acidic salt salts of the history of indonopyridine, their preparation and pharmaceutical preparations containing them | |
| US4156000A (en) | Cyclopenta[b]thiophene derivatives | |
| FI57592C (fi) | Analogifoerfarande foer framstaellning av terapeutiskt aktiva 5-(3-fenoxibensyl)-1h-tetrazoler |