SU604487A3 - Способ получени производных 3-аминоиндазолкарбоновой кислоты - Google Patents

Способ получени производных 3-аминоиндазолкарбоновой кислоты

Info

Publication number: SU604487A3
Authority: SU; USSR - Soviet Union
Prior art keywords: amino; acid; mol; carboxylic acid; ester
Prior art date: 1974-12-13

Application number

SU752195302A

Other languages

English (en)

Russian (ru)

Inventor

Майер Карл-Генрих

Петерзен Зигфрид

Клауке Эрих

Хоффмайстер Фридрих

Вуттке Вольфганг

Original Assignee

Байер Аг, (Фирма)

Priority date (The priority date 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 date listed.)

1974-12-13

Filing date

1975-12-08

Publication date

1978-04-25

1975-12-08 Application filed by Байер Аг, (Фирма) filed Critical Байер Аг, (Фирма)

1978-04-25 Application granted granted Critical

1978-04-25 Publication of SU604487A3 publication Critical patent/SU604487A3/ru

Links

238000000034 method Methods 0.000 title claims description 3
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 title 1
239000002253 acid Substances 0.000 claims description 37
125000000217 alkyl group Chemical group 0.000 claims description 7
230000003993 interaction Effects 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
YDTDKKULPWTHRV-UHFFFAOYSA-N 1H-indazol-3-amine Chemical compound C1=CC=C2C(N)=NNC2=C1 YDTDKKULPWTHRV-UHFFFAOYSA-N 0.000 claims description 3
239000011230 binding agent Substances 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
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 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims 3
239000001257 hydrogen Substances 0.000 claims 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
125000003282 alkyl amino group Chemical group 0.000 claims 2
125000005843 halogen group Chemical group 0.000 claims 2
241001331845 Equus asinus x caballus Species 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
125000004093 cyano group Chemical group *C#N 0.000 claims 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
150000002391 heterocyclic compounds Chemical class 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
238000006243 chemical reaction Methods 0.000 description 29
-1 3-amino-5trifluoromethyl-7 - isopropylaminoindazole Chemical compound 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
125000004494 ethyl ester group Chemical group 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 8
150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
BPTYMRSBTUERSW-UHFFFAOYSA-N 6-chloro-1h-indazol-3-amine Chemical compound ClC1=CC=C2C(N)=NNC2=C1 BPTYMRSBTUERSW-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
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 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 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
238000003756 stirring Methods 0.000 description 3
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
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 2
FWOPJXVQGMZKEP-UHFFFAOYSA-N 3-methyl-2h-indazole Chemical compound C1=CC=CC2=C(C)NN=C21 FWOPJXVQGMZKEP-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
QPLXQNVPEHUPTR-UHFFFAOYSA-N 4-chloro-1H-indazol-3-amine Chemical compound C1=CC(Cl)=C2C(N)=NNC2=C1 QPLXQNVPEHUPTR-UHFFFAOYSA-N 0.000 description 2
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 2
JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 2
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 2
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 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-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
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
239000002956 ash Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000005660 chlorination reaction Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000013078 crystal Substances 0.000 description 2
WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000003682 fluorination reaction Methods 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
150000003222 pyridines Chemical class 0.000 description 2
239000007858 starting material Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
GHFKCBWRZWDFKB-UHFFFAOYSA-N 1h-indazole-3,5-diamine Chemical compound C1=C(N)C=C2C(N)=NNC2=C1 GHFKCBWRZWDFKB-UHFFFAOYSA-N 0.000 description 1
QSACPWSIIRFHHR-UHFFFAOYSA-N 2,6-dimethylbenzonitrile Chemical compound CC1=CC=CC(C)=C1C#N QSACPWSIIRFHHR-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
CGXGSYJFRZNFAI-UHFFFAOYSA-N 2-chloro-3-(trichloromethyl)benzonitrile Chemical compound ClC1=C(C#N)C=CC=C1C(Cl)(Cl)Cl CGXGSYJFRZNFAI-UHFFFAOYSA-N 0.000 description 1
FFBTVTWIUALRIO-UHFFFAOYSA-N 2-chloro-6-(trichloromethyl)benzonitrile Chemical compound ClC1=CC=CC(C(Cl)(Cl)Cl)=C1C#N FFBTVTWIUALRIO-UHFFFAOYSA-N 0.000 description 1
DFPYRBFQHBGIKI-UHFFFAOYSA-N 2-chloro-6-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC=CC(Cl)=C1C#N DFPYRBFQHBGIKI-UHFFFAOYSA-N 0.000 description 1
MGOLNIXAPIAKFM-UHFFFAOYSA-N 2-isocyanato-2-methylpropane Chemical compound CC(C)(C)N=C=O MGOLNIXAPIAKFM-UHFFFAOYSA-N 0.000 description 1
GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
RFXALSFABPTLOY-UHFFFAOYSA-N 3-amino-5-chloro-n,n-dimethylindazole-1-carboxamide Chemical compound ClC1=CC=C2N(C(=O)N(C)C)N=C(N)C2=C1 RFXALSFABPTLOY-UHFFFAOYSA-N 0.000 description 1
WVVVMFDTENGKDM-UHFFFAOYSA-N 3-amino-7-nitro-1h-indazole-5-carbonitrile Chemical compound C1=C(C#N)C=C2C(N)=NNC2=C1[N+]([O-])=O WVVVMFDTENGKDM-UHFFFAOYSA-N 0.000 description 1
PEKCNRHPARPAHY-UHFFFAOYSA-N 3-amino-n,n-diethyl-5-methylindazole-1-carboxamide Chemical compound CC1=CC=C2N(C(=O)N(CC)CC)N=C(N)C2=C1 PEKCNRHPARPAHY-UHFFFAOYSA-N 0.000 description 1
QJJHWZXKLKDVJO-UHFFFAOYSA-N 3-aminoindazole-2-carboxylic acid Chemical compound C1=CC=CC2=C(N)N(C(O)=O)N=C21 QJJHWZXKLKDVJO-UHFFFAOYSA-N 0.000 description 1
HISBRTASAMYBQI-UHFFFAOYSA-N 3-methylindazole-1-carboxylic acid Chemical compound C1=CC=C2C(C)=NN(C(O)=O)C2=C1 HISBRTASAMYBQI-UHFFFAOYSA-N 0.000 description 1
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 1
ZUQOBHTUMCEQBG-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 ZUQOBHTUMCEQBG-UHFFFAOYSA-N 0.000 description 1
LIESSZYHGOCKPM-UHFFFAOYSA-N 4-methyl-7-propoxy-1h-indazol-3-amine Chemical compound CCCOC1=CC=C(C)C2=C1NN=C2N LIESSZYHGOCKPM-UHFFFAOYSA-N 0.000 description 1
CHIKJKNEGGLWAU-UHFFFAOYSA-N 5,7-dinitro-1h-indazol-3-amine Chemical compound C1=C([N+]([O-])=O)C=C2C(N)=NNC2=C1[N+]([O-])=O CHIKJKNEGGLWAU-UHFFFAOYSA-N 0.000 description 1
PLTWTHVTVXZIJR-UHFFFAOYSA-N 5-(trifluoromethyl)indazole-2,7-diamine Chemical compound NC1=CC(C(F)(F)F)=CC2=CN(N)N=C12 PLTWTHVTVXZIJR-UHFFFAOYSA-N 0.000 description 1
QCSQTZOPSNFNNX-UHFFFAOYSA-N 5-chloro-1h-indazol-3-amine Chemical compound C1=C(Cl)C=C2C(N)=NNC2=C1 QCSQTZOPSNFNNX-UHFFFAOYSA-N 0.000 description 1
YHMZEHSVPWGDDU-UHFFFAOYSA-N 5-ethoxy-1h-indazol-3-amine Chemical compound CCOC1=CC=C2NN=C(N)C2=C1 YHMZEHSVPWGDDU-UHFFFAOYSA-N 0.000 description 1
XCFCLXZHHWTVSS-UHFFFAOYSA-N 5-ethyl-6-propan-2-yl-1h-indazol-3-amine Chemical compound C1=C(C(C)C)C(CC)=CC2=C1NN=C2N XCFCLXZHHWTVSS-UHFFFAOYSA-N 0.000 description 1
ILHKBAOVOCDCSN-UHFFFAOYSA-N 5-n-methyl-1h-indazole-3,5-diamine Chemical compound CNC1=CC=C2NN=C(N)C2=C1 ILHKBAOVOCDCSN-UHFFFAOYSA-N 0.000 description 1
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 1
ONOMDYCVCWMQRN-UHFFFAOYSA-N 5-propan-2-yl-1h-indazol-3-amine Chemical compound CC(C)C1=CC=C2NN=C(N)C2=C1 ONOMDYCVCWMQRN-UHFFFAOYSA-N 0.000 description 1
BWHYEMMKOZBXKJ-UHFFFAOYSA-N 6-butyl-1h-indazol-3-amine Chemical compound CCCCC1=CC=C2C(N)=NNC2=C1 BWHYEMMKOZBXKJ-UHFFFAOYSA-N 0.000 description 1
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 1
JKOGFRGFWFEFNT-UHFFFAOYSA-N 6-fluoro-1h-indazol-3-amine Chemical compound FC1=CC=C2C(N)=NNC2=C1 JKOGFRGFWFEFNT-UHFFFAOYSA-N 0.000 description 1
HNOSKPXFWPKCPP-UHFFFAOYSA-N 6-methoxy-1h-indazol-3-amine Chemical compound COC1=CC=C2C(N)=NNC2=C1 HNOSKPXFWPKCPP-UHFFFAOYSA-N 0.000 description 1
LOXFRCAHUDJGFF-UHFFFAOYSA-N 7-n-butyl-5-(trifluoromethyl)-1h-indazole-3,7-diamine Chemical compound CCCCNC1=CC(C(F)(F)F)=CC2=C1NN=C2N LOXFRCAHUDJGFF-UHFFFAOYSA-N 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
ANLNUEIBIDNZMR-UHFFFAOYSA-N ClC1=CC=C2C(=CNC2=C1)N(C)C Chemical compound ClC1=CC=C2C(=CNC2=C1)N(C)C ANLNUEIBIDNZMR-UHFFFAOYSA-N 0.000 description 1
ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-N 0.000 description 1
235000002918 Fraxinus excelsior Nutrition 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
NGBSMPKFVQQLQJ-UHFFFAOYSA-N N-butyl-1H-indazol-3-amine Chemical compound C(CCC)NC1=NNC2=CC=CC=C12 NGBSMPKFVQQLQJ-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
XDFCIPNJCBUZJN-UHFFFAOYSA-N barium(2+) Chemical compound [Ba+2] XDFCIPNJCBUZJN-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
RGTXVXDNHPWPHH-UHFFFAOYSA-N butane-1,3-diamine Chemical compound CC(N)CCN RGTXVXDNHPWPHH-UHFFFAOYSA-N 0.000 description 1
CQMCIXZEONCDDH-UHFFFAOYSA-N butyl 3-amino-1h-indazole-5-carboxylate Chemical compound CCCCOC(=O)C1=CC=C2NN=C(N)C2=C1 CQMCIXZEONCDDH-UHFFFAOYSA-N 0.000 description 1
IFUMRBQXOOVRDP-UHFFFAOYSA-N butyl 3-formamidoindazole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OCCCC)N=C(NC=O)C2=C1 IFUMRBQXOOVRDP-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 1
150000004816 dichlorobenzenes Chemical class 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
FFYPMLJYZAEMQB-UHFFFAOYSA-N diethyl pyrocarbonate Chemical compound CCOC(=O)OC(=O)OCC FFYPMLJYZAEMQB-UHFFFAOYSA-N 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
BTXJXEHDKRWNMK-UHFFFAOYSA-N ethyl 3-amino-4-(trifluoromethyl)indazole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OCC)N=C(N)C2=C1C(F)(F)F BTXJXEHDKRWNMK-UHFFFAOYSA-N 0.000 description 1
YDKDPCUQIWVJOV-UHFFFAOYSA-N ethyl 3-amino-5,6-dimethoxyindazole-2-carboxylate Chemical compound C1=C(OC)C(OC)=CC2=C(N)N(C(=O)OCC)N=C21 YDKDPCUQIWVJOV-UHFFFAOYSA-N 0.000 description 1
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 1
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 1
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 1
238000001914 filtration Methods 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000005462 imide group Chemical group 0.000 description 1
DIDJZJDDXQPTLN-UHFFFAOYSA-N indazole-1-carboxylic acid Chemical compound C1=CC=C2N(C(=O)O)N=CC2=C1 DIDJZJDDXQPTLN-UHFFFAOYSA-N 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
150000002537 isoquinolines Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
MKARNSWMMBGSHX-UHFFFAOYSA-N m-xylylamine Natural products CC1=CC(C)=CC(N)=C1 MKARNSWMMBGSHX-UHFFFAOYSA-N 0.000 description 1
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 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
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000000203 mixture Substances 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
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 1
GQSVAVWMNZLSQR-UHFFFAOYSA-N n-methyl-5-(trifluoromethyl)-1h-indazol-3-amine Chemical compound C1=C(C(F)(F)F)C=C2C(NC)=NNC2=C1 GQSVAVWMNZLSQR-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-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
125000005493 quinolyl group Chemical group 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 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
239000002966 varnish Substances 0.000 description 1
239000008096 xylene Substances 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)

SU752195302A 1974-12-13 1975-12-08 Способ получени производных 3-аминоиндазолкарбоновой кислоты SU604487A3 (ru)

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
SU604487A3 true SU604487A3 (ru)	1978-04-25

Family

ID=5933305

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU752195302A SU604487A3 (ru)	1974-12-13	1975-12-08	Способ получени производных 3-аминоиндазолкарбоновой кислоты

Country Status (27)

Country	Link
US (1)	US4051252A (2)
JP (1)	JPS5182266A (2)
AT (1)	AT343653B (2)
BE (1)	BE836528A (2)
CA (1)	CA1059523A (2)
CH (1)	CH622250A5 (2)
CS (1)	CS189731B2 (2)
DD (1)	DD125484A5 (2)
DE (1)	DE2458965C3 (2)
DK (1)	DK137082C (2)
ES (1)	ES443429A1 (2)
FI (1)	FI753493A7 (2)
FR (1)	FR2293928A1 (2)
GB (1)	GB1490306A (2)
HK (1)	HK52580A (2)
HU (1)	HU173557B (2)
IE (1)	IE42208B1 (2)
IL (1)	IL48642A (2)
KE (1)	KE3078A (2)
LU (1)	LU73993A1 (2)
NL (1)	NL7514521A (2)
NO (1)	NO145382C (2)
PL (1)	PL99858B1 (2)
SE (1)	SE419645B (2)
SU (1)	SU604487A3 (2)
YU (1)	YU315275A (2)
ZA (1)	ZA757777B (2)

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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
US7473691B2 (en) *	2000-09-15	2009-01-06	Vertex Pharmaceuticals Incorporated	Pyrazole compounds useful as protein kinase inhibitors
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KR100406634B1 (ko) *	2001-03-12	2003-11-20	주식회사 엘지생명과학	3,5-디아미노인다졸 유도체, 그의 제조방법 및 사이클린의존성 키나아제 저해제로서의 그의 용도
WO2003028720A1 (en)	2001-09-26	2003-04-10	Pharmacia Italia S.P.A.	Aminoindazole derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions containing them
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AU2003218215A1 (en)	2002-03-15	2003-09-29	Vertex Pharmaceuticals, Inc.	Azolylaminoazines as inhibitors of protein kinases
JP4751063B2 (ja)	2002-05-17	2011-08-17	ファイザーイタリアソシエタアレスポンサビリタリミタータ	キナーゼ阻害剤として活性のアミノインダゾール誘導体、それらの調製方法、及びそれらを含む薬学的組成物
MY141867A (en) *	2002-06-20	2010-07-16	Vertex Pharma	Substituted pyrimidines useful as protein kinase inhibitors
DK1532145T3 (da)	2002-08-02	2007-01-15	Vertex Pharma	Pyrazolpræparater der er anvendelige som inhibitorer af GSK-3
JP2006512313A (ja) *	2002-10-31	2006-04-13	アムジェンインコーポレイテッド	抗炎症剤
WO2004072029A2 (en)	2003-02-06	2004-08-26	Vertex Pharmaceuticals Incorporated	Pyrazolopyridazines useful as inhibitors of protein kinases
AU2004297235A1 (en) *	2003-12-04	2005-06-23	Vertex Pharmaceuticals Incorporated	Quinoxalines useful as inhibitors of protein kinases
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AU2006279376B2 (en)	2005-08-18	2011-04-14	Vertex Pharmaceuticals Incoporated	Pyrazine kinase inhibitors
EP1954277B1 (en) *	2005-11-03	2017-01-18	Vertex Pharmaceuticals Incorporated	Aminopyrimidines useful as kinase inhibitors
BRPI0709963A2 (pt) *	2006-04-14	2011-08-02	Abbott Lab	processo para a preparação de indazolil uréias que inibem receptores de subtipo 1 de vanilóide (vr1)
MX2009004807A (es)	2006-11-02	2009-06-15	Vertex Pharma	Aminopiridinas y aminopirimidinas utiles como inhibidores de proteina cinasa.
NZ577768A (en)	2006-12-19	2012-01-12	Vertex Pharma	Aminopyrimidines useful as inhibitors of protein kinases
ATE526328T1 (de)	2007-03-09	2011-10-15	Vertex Pharma	Als inhibitoren von proteinkinasen geeignete aminopyrimidine
MX2009009592A (es)	2007-03-09	2009-11-10	Vertex Pharma	Aminopiridinas utiles como inhibidores de proteinas cinasas.
MX2009009590A (es)	2007-03-09	2009-11-10	Vertex Pharma	Aminopirimidinas utiles como inhibidores de proteinas cinasas.
AU2008240313A1 (en)	2007-04-13	2008-10-23	Aj Park	Aminopyrimidines useful as kinase inhibitors
JP5389786B2 (ja)	2007-05-02	2014-01-15	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	キナーゼ阻害として有用なアミノピリミジン
CN101679387A (zh) *	2007-05-02	2010-03-24	沃泰克斯药物股份有限公司	可用作激酶抑制剂的氨基嘧啶类化合物
AU2008247592A1 (en)	2007-05-02	2008-11-13	Vertex Pharmaceuticals Incorporated	Thiazoles and pyrazoles useful as kinase inhibitors
MX2009012719A (es) *	2007-05-24	2010-02-04	Vertex Pharma	Tiazoles y pirazoles utiles como inhibidores de cinasa.
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
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DE102009004245A1 (de)	2009-01-09	2010-07-15	Bayer Schering Pharma Aktiengesellschaft	Neue anellierte, Heteroatom-verbrückte Pyrazol- und Imidazol-Derivate und ihre Verwendung
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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
US3277100A (en) *	1963-05-31	1966-10-04	Du Pont	Novel substituted pyrazoles
NL6707299A (2) *	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 BE BE162651A patent/BE836528A/xx unknown
- 1975-12-11 HU HU75BA3349A patent/HU173557B/hu unknown
- 1975-12-11 DD DD190061A patent/DD125484A5/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 LU LU73993A patent/LU73993A1/xx unknown
- 1975-12-11 JP JP50146940A patent/JPS5182266A/ja active Pending
- 1975-12-11 PL PL1975185475A patent/PL99858B1/pl unknown
- 1975-12-11 AT AT939775A patent/AT343653B/de not_active IP Right Cessation
- 1975-12-12 FR FR7538124A patent/FR2293928A1/fr active Granted
- 1975-12-12 ZA ZA757777A patent/ZA757777B/xx unknown
- 1975-12-12 ES ES443429A patent/ES443429A1/es not_active Expired
- 1975-12-12 IE IE2714/75A patent/IE42208B1/en unknown
- 1975-12-12 YU YU03152/75A patent/YU315275A/xx unknown
- 1975-12-12 NL NL7514521A patent/NL7514521A/xx not_active Application Discontinuation
- 1975-12-12 DK DK567275A patent/DK137082C/da active
1980
- 1980-08-29 KE KE3078A patent/KE3078A/xx unknown
- 1980-09-18 HK HK525/80A patent/HK52580A/xx unknown

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2345070C2 (ru) *	2002-03-11	2009-01-27	Авентис Фарма С.А.	Производные аминоиндазолов в качестве лекарственных средств, способ их получения и содержащие их фармацевтические композиции

Also Published As

Publication number	Publication date
DE2458965A1 (de)	1976-06-16
KE3078A (en)	1980-10-03
AT343653B (de)	1978-06-12
SE419645B (sv)	1981-08-17
FR2293928B1 (2)	1979-09-21
PL99858B1 (pl)	1978-08-31
JPS5182266A (en)	1976-07-19
DE2458965C3 (de)	1979-10-11
GB1490306A (en)	1977-11-02
FR2293928A1 (fr)	1976-07-09
ATA939775A (de)	1977-10-15
IL48642A0 (en)	1976-02-29
ZA757777B (en)	1976-11-24
AU8717075A (en)	1977-06-09
HU173557B (hu)	1979-06-28
YU315275A (en)	1982-02-28
CA1059523A (en)	1979-07-31
FI753493A7 (2)	1976-06-14
DE2458965B2 (de)	1979-02-22
DK137082C (da)	1978-06-19
DK137082B (da)	1978-01-16
IE42208L (en)	1976-06-13
ES443429A1 (es)	1977-04-16
HK52580A (en)	1980-09-26
LU73993A1 (2)	1976-11-11
CH622250A5 (2)	1981-03-31
US4051252A (en)	1977-09-27
NO754024L (2)	1976-06-15
SE7513990L (sv)	1976-06-14
BE836528A (fr)	1976-06-11
DK567275A (da)	1976-06-14
NO145382C (no)	1982-03-10
DD125484A5 (2)	1977-04-20
NL7514521A (nl)	1976-06-15
NO145382B (no)	1981-11-30
IL48642A (en)	1979-12-30
CS189731B2 (en)	1979-04-30
IE42208B1 (en)	1980-06-18

Publication	Publication Date	Title
SU604487A3 (ru)	1978-04-25	Способ получени производных 3-аминоиндазолкарбоновой кислоты
JP2002541134A (ja)	2002-12-03	置換アニリン化合物
NO314456B1 (no)	2003-03-24	Fremgangsmåter og mellomprodukter nyttige for å fremstille antifolater
IE46269B1 (en)	1983-04-20	Isoxazole derivatives,process for their manufacture and preparations containing these compounds
US4994599A (en)	1991-02-19	Intermediates for producing quinolone-3-carboxylic acids
US4045429A (en)	1977-08-30	4-(4-Hydroxy- or acetoxy-3-carbomethoxyphenylazo)-benzenesulphonyl chloride
RO121211B1 (ro)	2007-01-30	Procedeu de preparare a 4-(heteroaril-metil)-1(2h)-ftalazinonelor
US4225716A (en)	1980-09-30	Process for the manufacture of 2,6-dichloropyridine derivatives
US3382246A (en)	1968-05-07	Certain 3-(2'-pyridyl)-4(3h)-quinazolones
US4895950A (en)	1990-01-23	5-halogeno-6-amino-nicotinic acid halides
JPH0841030A (ja)	1996-02-13	１−（ヘテロ）アリール−３−ヒドロキシピラゾールの製造方法
IE46102B1 (en)	1983-02-23	5-methylisoxazole-4-carboxylic acid anilides having pharmaceutical activity
JP4502280B2 (ja)	2010-07-14	スルファミンカルボン酸誘導体の製造方法
US2904553A (en)	1959-09-15	Tfflocarbonic acid esters and their
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SU604487A3 - Способ получени производных 3-аминоиндазолкарбоновой кислоты - Google Patents

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