CH622250A5 - - Google Patents
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- Publication number
- CH622250A5 CH622250A5 CH1599575A CH1599575A CH622250A5 CH 622250 A5 CH622250 A5 CH 622250A5 CH 1599575 A CH1599575 A CH 1599575A CH 1599575 A CH1599575 A CH 1599575A CH 622250 A5 CH622250 A5 CH 622250A5
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- indazole
- formula
- trifluoromethyl
- carboxylic acid
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 36
- -1 nitro, amino Chemical group 0.000 claims description 34
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 11
- 235000019253 formic acid Nutrition 0.000 claims description 11
- YDTDKKULPWTHRV-UHFFFAOYSA-N 1H-indazol-3-amine Chemical class C1=CC=C2C(N)=NNC2=C1 YDTDKKULPWTHRV-UHFFFAOYSA-N 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004442 acylamino group Chemical group 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 5
- ZQEIOHDJCAINLJ-UHFFFAOYSA-N 3-aminoindazole-3-carboxylic acid Chemical class C1=CC=C2C(N)(C(O)=O)N=NC2=C1 ZQEIOHDJCAINLJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 230000008018 melting Effects 0.000 description 53
- 238000002844 melting Methods 0.000 description 53
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 241000700159 Rattus Species 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 241001465754 Metazoa Species 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 12
- FFYPMLJYZAEMQB-UHFFFAOYSA-N diethyl pyrocarbonate Chemical compound CCOC(=O)OC(=O)OCC FFYPMLJYZAEMQB-UHFFFAOYSA-N 0.000 description 11
- 235000019441 ethanol Nutrition 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- ZFTFAPZRGNKQPU-UHFFFAOYSA-L carboxylato carbonate Chemical compound [O-]C(=O)OC([O-])=O ZFTFAPZRGNKQPU-UHFFFAOYSA-L 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 10
- ZXZTZRVCWTWKCH-UHFFFAOYSA-N 5-(trifluoromethyl)-1h-indazol-3-amine Chemical compound C1=C(C(F)(F)F)C=C2C(N)=NNC2=C1 ZXZTZRVCWTWKCH-UHFFFAOYSA-N 0.000 description 9
- BPTYMRSBTUERSW-UHFFFAOYSA-N 6-chloro-1h-indazol-3-amine Chemical compound ClC1=CC=C2C(N)=NNC2=C1 BPTYMRSBTUERSW-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 210000002683 foot Anatomy 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- 230000001754 anti-pyretic effect Effects 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 230000000202 analgesic effect Effects 0.000 description 7
- ZMPFPQFXUYYHSJ-UHFFFAOYSA-N 6-(trifluoromethyl)-1h-indazol-3-amine Chemical compound FC(F)(F)C1=CC=C2C(N)=NNC2=C1 ZMPFPQFXUYYHSJ-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 125000004494 ethyl ester group Chemical group 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 5
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 5
- HVSPPLIBICHWSB-UHFFFAOYSA-N 4-(trifluoromethyl)-1h-indazol-3-amine Chemical compound C1=CC(C(F)(F)F)=C2C(N)=NNC2=C1 HVSPPLIBICHWSB-UHFFFAOYSA-N 0.000 description 5
- 235000010418 carrageenan Nutrition 0.000 description 5
- 229920001525 carrageenan Polymers 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 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 4
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 4
- QPLXQNVPEHUPTR-UHFFFAOYSA-N 4-chloro-1H-indazol-3-amine Chemical compound C1=CC(Cl)=C2C(N)=NNC2=C1 QPLXQNVPEHUPTR-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 206010030113 Oedema Diseases 0.000 description 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 4
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 230000036760 body temperature Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 210000003169 central nervous system Anatomy 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 125000004663 dialkyl amino group Chemical group 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- CYYYIVVNEIXBKM-UHFFFAOYSA-N 3-amino-1h-indazole-5-carbonitrile Chemical compound C1=C(C#N)C=C2C(N)=NNC2=C1 CYYYIVVNEIXBKM-UHFFFAOYSA-N 0.000 description 3
- ZRBIRODWUCDBLY-UHFFFAOYSA-N 5-(trifluoromethyl)-1h-indazole-3,7-diamine Chemical compound C1=C(C(F)(F)F)C=C2C(N)=NNC2=C1N ZRBIRODWUCDBLY-UHFFFAOYSA-N 0.000 description 3
- RLNKCXFTRPDGAP-UHFFFAOYSA-N 7-(trifluoromethyl)-1h-indazol-3-amine Chemical compound C1=CC=C2C(N)=NNC2=C1C(F)(F)F RLNKCXFTRPDGAP-UHFFFAOYSA-N 0.000 description 3
- YNUURDFRONKMMP-UHFFFAOYSA-N 7-nitro-5-(trifluoromethyl)-1h-indazol-3-amine Chemical compound C1=C(C(F)(F)F)C=C2C(N)=NNC2=C1[N+]([O-])=O YNUURDFRONKMMP-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 230000003501 anti-edematous effect Effects 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 239000002221 antipyretic Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- YAGCIXJCAUGCGI-UHFFFAOYSA-N butoxycarbonyl butyl carbonate Chemical compound CCCCOC(=O)OC(=O)OCCCC YAGCIXJCAUGCGI-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- SQNFRGVSWXVJTJ-UHFFFAOYSA-N ethyl 3-aminoindazole-2-carboxylate Chemical compound C1=CC=CC2=C(N)N(C(=O)OCC)N=C21 SQNFRGVSWXVJTJ-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 230000008707 rearrangement Effects 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZEDPQIJYJCPIRM-UHFFFAOYSA-N 2,3-dimethylbenzonitrile Chemical compound CC1=CC=CC(C#N)=C1C ZEDPQIJYJCPIRM-UHFFFAOYSA-N 0.000 description 2
- QSACPWSIIRFHHR-UHFFFAOYSA-N 2,6-dimethylbenzonitrile Chemical compound CC1=CC=CC(C)=C1C#N QSACPWSIIRFHHR-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
- LBUPLFJQXQEYDT-UHFFFAOYSA-N 4,7-dichloro-1h-indazol-3-amine Chemical compound C1=CC(Cl)=C2C(N)=NNC2=C1Cl LBUPLFJQXQEYDT-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- SWZRTDLKPZAFDT-UHFFFAOYSA-N 5-nitro-1h-indazol-3-amine Chemical compound C1=C([N+]([O-])=O)C=C2C(N)=NNC2=C1 SWZRTDLKPZAFDT-UHFFFAOYSA-N 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
- WUWYYSMJEGBXJL-UHFFFAOYSA-N 6-chloro-n,n-dimethyl-1h-indazol-3-amine Chemical compound ClC1=CC=C2C(N(C)C)=NNC2=C1 WUWYYSMJEGBXJL-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- GZDFHIJNHHMENY-UHFFFAOYSA-N Dimethyl dicarbonate Chemical compound COC(=O)OC(=O)OC GZDFHIJNHHMENY-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- 206010037660 Pyrexia Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000004816 dichlorobenzenes Chemical class 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 235000010300 dimethyl dicarbonate Nutrition 0.000 description 2
- 229940113088 dimethylacetamide Drugs 0.000 description 2
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- YNLKWPAMJWFQTB-UHFFFAOYSA-N ethyl 3,7-diamino-5-(trifluoromethyl)indazole-2-carboxylate Chemical compound NC1=CC(C(F)(F)F)=CC2=C(N)N(C(=O)OCC)N=C21 YNLKWPAMJWFQTB-UHFFFAOYSA-N 0.000 description 2
- QPNBETJYGQOBNK-UHFFFAOYSA-N ethyl 3-amino-5-(ethoxycarbonylamino)indazole-1-carboxylate Chemical compound CCOC(=O)NC1=CC=C2N(C(=O)OCC)N=C(N)C2=C1 QPNBETJYGQOBNK-UHFFFAOYSA-N 0.000 description 2
- UGXOEWBGAICBHP-UHFFFAOYSA-N ethyl 3-amino-5-(trifluoromethyl)indazole-1-carboxylate Chemical compound FC(F)(F)C1=CC=C2N(C(=O)OCC)N=C(N)C2=C1 UGXOEWBGAICBHP-UHFFFAOYSA-N 0.000 description 2
- HXVNAFZATKDCQT-UHFFFAOYSA-N ethyl 3-amino-5-(trifluoromethyl)indazole-2-carboxylate Chemical compound C1=CC(C(F)(F)F)=CC2=C(N)N(C(=O)OCC)N=C21 HXVNAFZATKDCQT-UHFFFAOYSA-N 0.000 description 2
- CLWMVTQOGTXMIA-UHFFFAOYSA-N ethyl 3-amino-6-chloroindazole-1-carboxylate Chemical compound C1=C(Cl)C=C2N(C(=O)OCC)N=C(N)C2=C1 CLWMVTQOGTXMIA-UHFFFAOYSA-N 0.000 description 2
- UVAXVHRHEUHJJK-UHFFFAOYSA-N ethyl 3-amino-6-chloroindazole-2-carboxylate Chemical compound C1=C(Cl)C=CC2=C(N)N(C(=O)OCC)N=C21 UVAXVHRHEUHJJK-UHFFFAOYSA-N 0.000 description 2
- MIKBUCCDOOVIMQ-UHFFFAOYSA-N ethyl 6-chloro-3-(dimethylamino)indazole-1-carboxylate Chemical compound C1=C(Cl)C=C2N(C(=O)OCC)N=C(N(C)C)C2=C1 MIKBUCCDOOVIMQ-UHFFFAOYSA-N 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- FCVFXSHIKIITAJ-UHFFFAOYSA-N methyl 3-amino-5-(trifluoromethyl)indazole-2-carboxylate Chemical compound C1=CC(C(F)(F)F)=CC2=C(N)N(C(=O)OC)N=C21 FCVFXSHIKIITAJ-UHFFFAOYSA-N 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical class CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- VZCVKAIITHUUIJ-UHFFFAOYSA-N n-[5-(trifluoromethyl)-1h-indazol-3-yl]formamide Chemical compound FC(F)(F)C1=CC=C2NN=C(NC=O)C2=C1 VZCVKAIITHUUIJ-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
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- 239000008187 granular material Substances 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([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
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- URMZNKZRXMLCQA-UHFFFAOYSA-N methyl 3-amino-4-(trifluoromethyl)indazole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC)N=C(N)C2=C1C(F)(F)F URMZNKZRXMLCQA-UHFFFAOYSA-N 0.000 description 1
- PRXDPXWCRZZANM-UHFFFAOYSA-N methyl 3-amino-4-chloroindazole-2-carboxylate Chemical compound C1=CC=C(Cl)C2=C(N)N(C(=O)OC)N=C21 PRXDPXWCRZZANM-UHFFFAOYSA-N 0.000 description 1
- RHNHZZJVHSIFSH-UHFFFAOYSA-N methyl 3-amino-5-(trifluoromethyl)indazole-1-carboxylate Chemical compound FC(F)(F)C1=CC=C2N(C(=O)OC)N=C(N)C2=C1 RHNHZZJVHSIFSH-UHFFFAOYSA-N 0.000 description 1
- GUSXMGLDONQZKF-UHFFFAOYSA-N methyl 3-amino-5-cyanoindazole-2-carboxylate Chemical compound C1=CC(C#N)=CC2=C(N)N(C(=O)OC)N=C21 GUSXMGLDONQZKF-UHFFFAOYSA-N 0.000 description 1
- RCVKOTDDPFBOOM-UHFFFAOYSA-N methyl 3-amino-6-chloroindazole-1-carboxylate Chemical compound C1=C(Cl)C=C2N(C(=O)OC)N=C(N)C2=C1 RCVKOTDDPFBOOM-UHFFFAOYSA-N 0.000 description 1
- PVKQIUATGHWTPS-UHFFFAOYSA-N methyl 3-aminoindazole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC)N=C(N)C2=C1 PVKQIUATGHWTPS-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-N methyl hydrogen carbonate Chemical class COC(O)=O CXHHBNMLPJOKQD-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- HYNKVGHPJRHDMR-UHFFFAOYSA-N n,n-dimethyl-1h-indazol-3-amine Chemical compound C1=CC=C2C(N(C)C)=NNC2=C1 HYNKVGHPJRHDMR-UHFFFAOYSA-N 0.000 description 1
- WIWOGKHWCFGIJI-UHFFFAOYSA-N n,n-dimethyl-5-(trifluoromethyl)-1h-indazol-3-amine Chemical compound C1=C(C(F)(F)F)C=C2C(N(C)C)=NNC2=C1 WIWOGKHWCFGIJI-UHFFFAOYSA-N 0.000 description 1
- DTGTVHOEAJUCNV-UHFFFAOYSA-N n-(1h-indazol-3-yl)formamide Chemical compound C1=CC=C2C(NC=O)=NNC2=C1 DTGTVHOEAJUCNV-UHFFFAOYSA-N 0.000 description 1
- CKJASMQLNKTQIV-UHFFFAOYSA-N n-(3-amino-1h-indazol-5-yl)-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=CC=C2NN=C(N)C2=C1 CKJASMQLNKTQIV-UHFFFAOYSA-N 0.000 description 1
- OWPZTVIPDASKEH-UHFFFAOYSA-N n-(3-amino-1h-indazol-5-yl)acetamide Chemical compound CC(=O)NC1=CC=C2NN=C(N)C2=C1 OWPZTVIPDASKEH-UHFFFAOYSA-N 0.000 description 1
- ODNUDOVOVFEZFC-UHFFFAOYSA-N n-(3-amino-1h-indazol-5-yl)formamide Chemical compound C1=C(NC=O)C=C2C(N)=NNC2=C1 ODNUDOVOVFEZFC-UHFFFAOYSA-N 0.000 description 1
- XVNPFBZCDIAZJH-UHFFFAOYSA-N n-(3-amino-5-cyano-1h-indazol-7-yl)formamide Chemical compound C1=C(C#N)C=C2C(N)=NNC2=C1NC=O XVNPFBZCDIAZJH-UHFFFAOYSA-N 0.000 description 1
- VCOFYXZSTMAJJI-UHFFFAOYSA-N n-(3-amino-7-formamido-1h-indazol-5-yl)formamide Chemical compound C1=C(NC=O)C=C2C(N)=NNC2=C1NC=O VCOFYXZSTMAJJI-UHFFFAOYSA-N 0.000 description 1
- AEWJVRSPWHVSCC-UHFFFAOYSA-N n-(5-ethyl-1h-indazol-3-yl)formamide Chemical compound CCC1=CC=C2NN=C(NC=O)C2=C1 AEWJVRSPWHVSCC-UHFFFAOYSA-N 0.000 description 1
- MGDNHIJGIWHQBL-UHFFFAOYSA-N n-ethyl-n-methylacetamide Chemical compound CCN(C)C(C)=O MGDNHIJGIWHQBL-UHFFFAOYSA-N 0.000 description 1
- SDEZUJWLTFBSMR-UHFFFAOYSA-N n-methyl-1h-indazol-3-amine Chemical compound C1=CC=C2C(NC)=NNC2=C1 SDEZUJWLTFBSMR-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229940127240 opiate Drugs 0.000 description 1
- 230000037040 pain threshold Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- VFNMMLCUAXGPPH-UHFFFAOYSA-N propan-2-yl 3-amino-5-(trifluoromethyl)indazole-1-carboxylate Chemical compound FC(F)(F)C1=CC=C2N(C(=O)OC(C)C)N=C(N)C2=C1 VFNMMLCUAXGPPH-UHFFFAOYSA-N 0.000 description 1
- PBHKWJXDCQXJEB-UHFFFAOYSA-N propan-2-yl 3-amino-5-(trifluoromethyl)indazole-2-carboxylate Chemical compound C1=CC(C(F)(F)F)=CC2=C(N)N(C(=O)OC(C)C)N=C21 PBHKWJXDCQXJEB-UHFFFAOYSA-N 0.000 description 1
- AHIHJODVQGBOND-UHFFFAOYSA-N propan-2-yl hydrogen carbonate Chemical class CC(C)OC(O)=O AHIHJODVQGBOND-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- DEFISFGOVQSEPX-UHFFFAOYSA-N propyl 5-chloro-3-(dimethylamino)indazole-1-carboxylate Chemical compound ClC1=CC=C2N(C(=O)OCCC)N=C(N(C)C)C2=C1 DEFISFGOVQSEPX-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FOWDZVNRQHPXDO-UHFFFAOYSA-N propyl hydrogen carbonate Chemical class CCCOC(O)=O FOWDZVNRQHPXDO-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000008117 stearic acid 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
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2458965A DE2458965C3 (de) | 1974-12-13 | 1974-12-13 | 3-Amino-indazol-N-carbonsäure-Derivate, Verfahren zu ihrer Herstellung sowie sie enthaltende Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH622250A5 true CH622250A5 (OSRAM) | 1981-03-31 |
Family
ID=5933305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1599575A CH622250A5 (OSRAM) | 1974-12-13 | 1975-12-09 |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4051252A (OSRAM) |
| JP (1) | JPS5182266A (OSRAM) |
| AT (1) | AT343653B (OSRAM) |
| BE (1) | BE836528A (OSRAM) |
| CA (1) | CA1059523A (OSRAM) |
| CH (1) | CH622250A5 (OSRAM) |
| CS (1) | CS189731B2 (OSRAM) |
| DD (1) | DD125484A5 (OSRAM) |
| DE (1) | DE2458965C3 (OSRAM) |
| DK (1) | DK137082C (OSRAM) |
| ES (1) | ES443429A1 (OSRAM) |
| FI (1) | FI753493A7 (OSRAM) |
| FR (1) | FR2293928A1 (OSRAM) |
| GB (1) | GB1490306A (OSRAM) |
| HK (1) | HK52580A (OSRAM) |
| HU (1) | HU173557B (OSRAM) |
| IE (1) | IE42208B1 (OSRAM) |
| IL (1) | IL48642A (OSRAM) |
| KE (1) | KE3078A (OSRAM) |
| LU (1) | LU73993A1 (OSRAM) |
| NL (1) | NL7514521A (OSRAM) |
| NO (1) | NO145382C (OSRAM) |
| PL (1) | PL99858B1 (OSRAM) |
| SE (1) | SE419645B (OSRAM) |
| SU (1) | SU604487A3 (OSRAM) |
| YU (1) | YU315275A (OSRAM) |
| ZA (1) | ZA757777B (OSRAM) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4431657A (en) * | 1982-05-24 | 1984-02-14 | Ayerst, Mckenna & Harrison Inc. | Analgesic compositions consisting of 2H-benzothieno[3,2-c]pyrazol-3-amine derivatives |
| KR20010086657A (ko) * | 2000-03-02 | 2001-09-15 | 성재갑 | 아미노인다졸 유도체 및 이를 함유하는 싸이클린 의존키나아제 저해제 조성물 |
| KR20030030005A (ko) * | 2000-09-15 | 2003-04-16 | 버텍스 파마슈티칼스 인코포레이티드 | 단백질 키나제 억제제로서 유용한 피라졸 화합물 |
| US6660731B2 (en) | 2000-09-15 | 2003-12-09 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| US7473691B2 (en) * | 2000-09-15 | 2009-01-06 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| EP1698627A1 (en) * | 2000-09-15 | 2006-09-06 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| CN1926132B (zh) * | 2000-09-15 | 2010-12-29 | 沃泰克斯药物股份有限公司 | 可用作蛋白激酶抑制剂的吡唑化合物 |
| EP1345927B1 (en) | 2000-12-21 | 2006-05-17 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| KR100406634B1 (ko) * | 2001-03-12 | 2003-11-20 | 주식회사 엘지생명과학 | 3,5-디아미노인다졸 유도체, 그의 제조방법 및 사이클린의존성 키나아제 저해제로서의 그의 용도 |
| DE60238999D1 (de) | 2001-09-26 | 2011-03-03 | Pfizer Italia Srl | Aminoindazolderivate mit kinaseinhibierender wirkung, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen |
| PL372198A1 (en) * | 2002-02-06 | 2005-07-11 | Vertex Pharmaceuticals Incorporated | Heteroaryl compounds useful as inhibitors of gsk-3 |
| FR2836915B1 (fr) * | 2002-03-11 | 2008-01-11 | Aventis Pharma Sa | Derives d'aminoindazoles, procede de preparation et intermediaires de ce procede a titre de medicaments et compositions pharmaceutiques les renfermant |
| WO2003078427A1 (en) | 2002-03-15 | 2003-09-25 | Vertex Pharmaceuticals, Inc. | Azolylaminoazines as inhibitors of protein kinases |
| BR0311291A (pt) | 2002-05-17 | 2005-03-29 | Pharmacia Italia Spa | Derivados de aminoindazol ativos como inibidores da cinase, processo para sua preparação e composições farmacêuticas compreendendo os mesmos |
| MY141867A (en) * | 2002-06-20 | 2010-07-16 | Vertex Pharma | Substituted pyrimidines useful as protein kinase inhibitors |
| KR20050032105A (ko) | 2002-08-02 | 2005-04-06 | 버텍스 파마슈티칼스 인코포레이티드 | Ｇｓｋ-3의 억제제로서 유용한 피라졸 조성물 |
| WO2004041285A1 (en) * | 2002-10-31 | 2004-05-21 | Amgen Inc. | Antiinflammation agents |
| US7601718B2 (en) | 2003-02-06 | 2009-10-13 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of protein kinases |
| CA2548172A1 (en) * | 2003-12-04 | 2005-06-23 | Vertex Pharmaceuticals Incorporated | Quinoxalines useful as inhibitors of protein kinases |
| DE102004005172A1 (de) | 2004-02-02 | 2005-08-18 | Aventis Pharma Deutschland Gmbh | Indazolderivate als Inhibitoren der Hormon Sensitiven Lipase |
| ATE542814T1 (de) | 2005-08-18 | 2012-02-15 | Vertex Pharma | Pyrazinkinaseinhibitoren |
| WO2007056163A2 (en) | 2005-11-03 | 2007-05-18 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines useful as kinase inhibitors |
| KR101118932B1 (ko) * | 2006-04-14 | 2012-02-27 | 아보트 러보러터리즈 | 바닐로이드 서브타입 1(ｖｒ1) 수용체를 억제하는 인다졸릴우레아의 제조방법 |
| WO2008057940A1 (en) | 2006-11-02 | 2008-05-15 | Vertex Pharmaceuticals Incorporated | Aminopyridines and aminopyrimidines useful as inhibitors of protein kinases |
| DE602007007985D1 (de) | 2006-12-19 | 2010-09-02 | Vertex Pharma | Als inhibitoren von proteinkinasen geeignete aminopyrimidine |
| CA2679884A1 (en) | 2007-03-09 | 2008-09-18 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines useful as inhibitors of protein kinases |
| RU2009137390A (ru) | 2007-03-09 | 2011-04-20 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Аминопиримидины, пригодные в качестве ингибиторов протеинкиназ |
| AU2008226461A1 (en) | 2007-03-09 | 2008-09-18 | Vertex Pharmaceuticals Incorporated | Aminopyridines useful as inhibitors of protein kinases |
| EP2146982A2 (en) | 2007-04-13 | 2010-01-27 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines useful as kinase inhibitors |
| EP2155730A2 (en) * | 2007-05-02 | 2010-02-24 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines useful as kinase inhibitors |
| EP2152694A2 (en) * | 2007-05-02 | 2010-02-17 | Vertex Pharmaceuticals Incorporated | Thiazoles and pyrazoles useful as kinase inhibitors |
| CA2694381A1 (en) | 2007-05-02 | 2008-11-13 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines useful as kinase inhibitors |
| CN101687852A (zh) * | 2007-05-24 | 2010-03-31 | 沃泰克斯药物股份有限公司 | 可用作激酶抑制剂的噻唑类和吡唑类化合物 |
| CN101790532B (zh) | 2007-07-31 | 2013-11-20 | 沃泰克斯药物股份有限公司 | 5-氟-1H-吡唑并[3，4-b]吡啶-3-胺及其衍生物的制备方法 |
| JP2012501971A (ja) * | 2008-09-03 | 2012-01-26 | バーテックス ファーマシューティカルズ インコーポレイテッド | 共結晶および共結晶を含む薬学的処方物 |
| DE102009004245A1 (de) | 2009-01-09 | 2010-07-15 | Bayer Schering Pharma Aktiengesellschaft | Neue anellierte, Heteroatom-verbrückte Pyrazol- und Imidazol-Derivate und ihre Verwendung |
| SI2890684T1 (en) | 2012-07-24 | 2018-06-29 | Bial-Portela & Ca, S.A. | THE CLOTHING MACHINE AND THEIR USE AS ENCLOSURE INHIBITORS |
| EP2882712A2 (en) * | 2012-07-27 | 2015-06-17 | BIAL - Portela & Cª S.A. | Process for the synthesis of substituted urea compounds |
| LT3024825T (lt) | 2013-07-24 | 2017-12-11 | Bial - Portela & C, S.A. | Imidazolo karboksamidai ir jų panaudojimas kaip faah inhibitorių |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3133081A (en) * | 1964-05-12 | J-aminoindazole derivatives | ||
| CH397698A (de) * | 1961-09-08 | 1965-08-31 | Siegfried Ag | Verfahren zur Herstellung neuer 1-Carbamyl-indazole |
| US3274203A (en) * | 1963-05-31 | 1966-09-20 | Du Pont | 1-carbamyl and thiocarbamyl-3-amino-4-nonsubstituted and substituted pyrazoles |
| NL6707299A (OSRAM) * | 1966-07-16 | 1968-01-17 | ||
| DE1770649A1 (de) * | 1968-06-15 | 1971-11-11 | Bayer Ag | Substituierte 3-Amino-indazole |
-
1974
- 1974-12-13 DE DE2458965A patent/DE2458965C3/de not_active Expired
-
1975
- 1975-10-28 GB GB44299/75A patent/GB1490306A/en not_active Expired
- 1975-11-24 US US05/634,914 patent/US4051252A/en not_active Expired - Lifetime
- 1975-11-27 CA CA240,662A patent/CA1059523A/en not_active Expired
- 1975-11-28 NO NO754024A patent/NO145382C/no unknown
- 1975-12-02 CS CS758165A patent/CS189731B2/cs unknown
- 1975-12-08 SU SU752195302A patent/SU604487A3/ru active
- 1975-12-09 CH CH1599575A patent/CH622250A5/de not_active IP Right Cessation
- 1975-12-10 IL IL48642A patent/IL48642A/xx unknown
- 1975-12-11 FI FI753493A patent/FI753493A7/fi not_active Application Discontinuation
- 1975-12-11 SE SE7513990A patent/SE419645B/xx unknown
- 1975-12-11 AT AT939775A patent/AT343653B/de not_active IP Right Cessation
- 1975-12-11 PL PL1975185475A patent/PL99858B1/pl unknown
- 1975-12-11 DD DD190061A patent/DD125484A5/xx unknown
- 1975-12-11 JP JP50146940A patent/JPS5182266A/ja active Pending
- 1975-12-11 HU HU75BA3349A patent/HU173557B/hu unknown
- 1975-12-11 BE BE162651A patent/BE836528A/xx unknown
- 1975-12-11 LU LU73993A patent/LU73993A1/xx unknown
- 1975-12-12 NL NL7514521A patent/NL7514521A/xx not_active Application Discontinuation
- 1975-12-12 FR FR7538124A patent/FR2293928A1/fr active Granted
- 1975-12-12 YU YU03152/75A patent/YU315275A/xx unknown
- 1975-12-12 IE IE2714/75A patent/IE42208B1/en unknown
- 1975-12-12 DK DK567275A patent/DK137082C/da active
- 1975-12-12 ES ES443429A patent/ES443429A1/es not_active Expired
- 1975-12-12 ZA ZA757777A patent/ZA757777B/xx unknown
-
1980
- 1980-08-29 KE KE3078A patent/KE3078A/xx unknown
- 1980-09-18 HK HK525/80A patent/HK52580A/xx unknown
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| PL | Patent ceased | ||
| PL | Patent ceased |