MXPA06004043A

MXPA06004043A - 2h-[1,2,4]triazolo[4,3-a]pirazinas sustituidas como inhibidores de la glucogeno sintetasa cinasa 3.

2h-[1,2,4]triazolo[4,3-a]pirazinas sustituidas como inhibidores de la glucogeno sintetasa cinasa 3.

Info

Publication number: MXPA06004043A
Authority: MX; Mexico
Prior art keywords: independently; optionally substituted; tert; butyl; pyrazin
Prior art date: 2003-10-10

Application number

MXPA06004043A

Other languages

English (en)

Spanish (es)

Inventor

John William Benbow

Original Assignee

Pfizer Prod Inc

Priority date

2003-10-10

Filing date

2004-09-27

Publication date

2006-06-28

2004-09-27 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2006-06-28 Publication of MXPA06004043A publication Critical patent/MXPA06004043A/es

Links

239000003112 inhibitor Substances 0.000 title claims description 28
SETPVHMQKAXDMY-UHFFFAOYSA-N 2,3-dihydro-[1,2,4]triazolo[4,3-a]pyrazine Chemical class C1=NC=CN2CNN=C21 SETPVHMQKAXDMY-UHFFFAOYSA-N 0.000 title 1
101150090422 gsk-3 gene Proteins 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 134
239000000651 prodrug Substances 0.000 claims abstract description 51
229940002612 prodrug Drugs 0.000 claims abstract description 51
150000003839 salts Chemical class 0.000 claims abstract description 30
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
-1 methylenedioxy Chemical group 0.000 claims description 109
125000000217 alkyl group Chemical group 0.000 claims description 90
239000000203 mixture Substances 0.000 claims description 75
125000003118 aryl group Chemical group 0.000 claims description 57
229910052736 halogen Inorganic materials 0.000 claims description 56
150000002367 halogens Chemical class 0.000 claims description 52
125000003545 alkoxy group Chemical group 0.000 claims description 45
125000001072 heteroaryl group Chemical group 0.000 claims description 42
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 36
125000004093 cyano group Chemical group *C#N 0.000 claims description 30
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 24
LAQJGAKLLZAETL-UHFFFAOYSA-N 2h-pyrazin-3-one Chemical compound O=C1CN=CC=N1 LAQJGAKLLZAETL-UHFFFAOYSA-N 0.000 claims description 23
125000000753 cycloalkyl group Chemical group 0.000 claims description 19
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
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125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 12
239000003795 chemical substances by application Substances 0.000 claims description 12
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125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
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RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 claims description 2
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CJOFXWAVKWHTFT-XSFVSMFZSA-N fluvoxamine Chemical compound COCCCC\C(=N/OCCN)C1=CC=C(C(F)(F)F)C=C1 CJOFXWAVKWHTFT-XSFVSMFZSA-N 0.000 claims description 2
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QOIGKGMMAGJZNZ-UHFFFAOYSA-N gepirone Chemical compound O=C1CC(C)(C)CC(=O)N1CCCCN1CCN(C=2N=CC=CN=2)CC1 QOIGKGMMAGJZNZ-UHFFFAOYSA-N 0.000 claims description 2
229960001952 metrifonate Drugs 0.000 claims description 2
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RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 claims description 2
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WNUQCGWXPNGORO-NRFANRHFSA-N sonepiprazole Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1CCN(CC[C@H]2C3=CC=CC=C3CCO2)CC1 WNUQCGWXPNGORO-NRFANRHFSA-N 0.000 claims description 2
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NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 claims description 2
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125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
POLAUOGHQIDJOL-UHFFFAOYSA-N 3-[(6-tert-butyl-3-oxo-2h-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)amino]propanenitrile Chemical compound N#CCCNC1=NC(C(C)(C)C)=CN2C(=O)NN=C21 POLAUOGHQIDJOL-UHFFFAOYSA-N 0.000 claims 1
ZVICCLKJAFIQPK-UHFFFAOYSA-N 5-methyl-6-propan-2-yl-8-(2-pyridin-3-ylethylamino)-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound C12=NNC(=O)N2C(C)=C(C(C)C)N=C1NCCC1=CC=CN=C1 ZVICCLKJAFIQPK-UHFFFAOYSA-N 0.000 claims 1
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