JP2007504243A5 - - Google Patents
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- JP2007504243A5 JP2007504243A5 JP2006525454A JP2006525454A JP2007504243A5 JP 2007504243 A5 JP2007504243 A5 JP 2007504243A5 JP 2006525454 A JP2006525454 A JP 2006525454A JP 2006525454 A JP2006525454 A JP 2006525454A JP 2007504243 A5 JP2007504243 A5 JP 2007504243A5
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- JP
- Japan
- Prior art keywords
- alkyl
- amino
- alkoxy
- substituted
- mono
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- -1 tri-substituted phenyl Chemical group 0.000 claims 276
- 229910052736 halogen Inorganic materials 0.000 claims 148
- 125000000753 cycloalkyl group Chemical group 0.000 claims 128
- 150000002367 halogens Chemical class 0.000 claims 125
- 150000001875 compounds Chemical class 0.000 claims 115
- 150000003839 salts Chemical class 0.000 claims 115
- 125000001424 substituent group Chemical group 0.000 claims 104
- 125000004093 cyano group Chemical group *C#N 0.000 claims 99
- 229930195733 hydrocarbon Natural products 0.000 claims 84
- 125000000217 alkyl group Chemical group 0.000 claims 62
- 229910052739 hydrogen Inorganic materials 0.000 claims 62
- 239000001257 hydrogen Substances 0.000 claims 62
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 48
- 150000002431 hydrogen Chemical class 0.000 claims 47
- 125000003282 alkyl amino group Chemical group 0.000 claims 43
- 239000004215 Carbon black (E152) Substances 0.000 claims 40
- 125000005843 halogen group Chemical group 0.000 claims 38
- 125000004076 pyridyl group Chemical group 0.000 claims 36
- 125000004043 oxo group Chemical group O=* 0.000 claims 35
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 34
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 29
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 29
- 125000001072 heteroaryl group Chemical class 0.000 claims 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 26
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 25
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 25
- 150000002430 hydrocarbons Chemical class 0.000 claims 25
- 229910052760 oxygen Inorganic materials 0.000 claims 24
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 22
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 22
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 21
- 125000003545 alkoxy group Chemical group 0.000 claims 21
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 21
- 229910052757 nitrogen Inorganic materials 0.000 claims 20
- 125000002393 azetidinyl group Chemical group 0.000 claims 19
- 125000005047 dihydroimidazolyl group Chemical group N1(CNC=C1)* 0.000 claims 19
- 125000002757 morpholinyl group Chemical group 0.000 claims 19
- 125000004193 piperazinyl group Chemical group 0.000 claims 19
- 125000003386 piperidinyl group Chemical group 0.000 claims 19
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 19
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims 19
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 19
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 19
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 18
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 17
- 125000003118 aryl group Chemical group 0.000 claims 16
- 229910052717 sulfur Inorganic materials 0.000 claims 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 11
- 108010056643 Corticotropin-Releasing Hormone Receptors Proteins 0.000 claims 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 10
- 125000005842 heteroatom Chemical group 0.000 claims 10
- 239000001301 oxygen Substances 0.000 claims 10
- 210000004027 cell Anatomy 0.000 claims 9
- 125000004663 dialkyl amino group Chemical group 0.000 claims 9
- 125000003373 pyrazinyl group Chemical group 0.000 claims 9
- 125000004103 aminoalkyl group Chemical group 0.000 claims 8
- 125000002541 furyl group Chemical group 0.000 claims 8
- 125000001188 haloalkyl group Chemical group 0.000 claims 8
- 125000000842 isoxazolyl group Chemical group 0.000 claims 8
- 125000002971 oxazolyl group Chemical group 0.000 claims 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims 8
- 229920006395 saturated elastomer Polymers 0.000 claims 8
- 125000000335 thiazolyl group Chemical group 0.000 claims 8
- 125000001544 thienyl group Chemical group 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000001425 triazolyl group Chemical group 0.000 claims 7
- 125000006165 cyclic alkyl group Chemical group 0.000 claims 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 6
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims 6
- 238000006467 substitution reaction Methods 0.000 claims 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 5
- 125000004122 cyclic group Chemical group 0.000 claims 5
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims 5
- 238000000338 in vitro Methods 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 239000000243 solution Substances 0.000 claims 5
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims 5
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 5
- 150000003457 sulfones Chemical class 0.000 claims 5
- 150000003462 sulfoxides Chemical class 0.000 claims 5
- 239000011593 sulfur Substances 0.000 claims 5
- 125000005942 tetrahydropyridyl group Chemical group 0.000 claims 5
- 125000001589 carboacyl group Chemical group 0.000 claims 4
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims 4
- 238000002360 preparation method Methods 0.000 claims 4
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 3
- 125000005432 dialkylcarboxamide group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 238000001525 receptor binding assay Methods 0.000 claims 3
- 125000006413 ring segment Chemical group 0.000 claims 3
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 2
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims 2
- USDIRSJFHPHMAS-UHFFFAOYSA-N ClC1=NC=C(C=2C1=NC=CN=2)F Chemical compound ClC1=NC=C(C=2C1=NC=CN=2)F USDIRSJFHPHMAS-UHFFFAOYSA-N 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- 108010052164 Sodium Channels Proteins 0.000 claims 2
- 102000018674 Sodium Channels Human genes 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 239000012085 test solution Substances 0.000 claims 2
- 238000005406 washing Methods 0.000 claims 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims 1
- JIFOURNCJACCCO-UHFFFAOYSA-N 1-(1,3-dimethoxypropan-2-yl)-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrazolo[3,4-b]pyrazine Chemical compound CC=1N=C2N(C(COC)COC)N=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC JIFOURNCJACCCO-UHFFFAOYSA-N 0.000 claims 1
- CFUVRYWPAMHGFL-UHFFFAOYSA-N 1-(1,3-dimethoxypropan-2-yl)-6-ethyl-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3-methylpyrazolo[3,4-b]pyrazine Chemical compound CCC1=NC=2N(C(COC)COC)N=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1OC CFUVRYWPAMHGFL-UHFFFAOYSA-N 0.000 claims 1
- OBFRJIYJGOMGEP-UHFFFAOYSA-N 1-[3-(6-ethyl-3-methyl-1-pentan-3-ylpyrazolo[3,4-b]pyrazin-5-yl)-6-propan-2-ylpyridin-2-yl]-n,n-dimethylpyrrolidin-3-amine Chemical compound CCC=1N=C2N(C(CC)CC)N=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1N1CCC(N(C)C)C1 OBFRJIYJGOMGEP-UHFFFAOYSA-N 0.000 claims 1
- JMMZEWGMUIBGDU-UHFFFAOYSA-N 1-benzyl-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrazolo[3,4-b]pyrazine Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=N1)C)=NC2=C1N(CC=1C=CC=CC=1)N=C2C JMMZEWGMUIBGDU-UHFFFAOYSA-N 0.000 claims 1
- KVGGSTUZMLEFFK-UHFFFAOYSA-N 2-[6-ethyl-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3-methylpyrazolo[3,4-b]pyrazin-1-yl]-3-methoxypropan-1-ol Chemical compound CCC1=NC=2N(C(CO)COC)N=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1OC KVGGSTUZMLEFFK-UHFFFAOYSA-N 0.000 claims 1
- WJJMQBQGTHXSJX-UHFFFAOYSA-N 2-[[3-(6-ethyl-3-methyl-1-pentan-3-ylpyrazolo[3,4-b]pyrazin-5-yl)-6-propan-2-ylpyridin-2-yl]-methylamino]ethanol Chemical compound CCC=1N=C2N(C(CC)CC)N=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1N(C)CCO WJJMQBQGTHXSJX-UHFFFAOYSA-N 0.000 claims 1
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims 1
- BUDHDLJHCYFGNX-UHFFFAOYSA-N 3-(1-benzyl-6-ethyl-3-methylpyrazolo[3,4-b]pyrazin-5-yl)-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound N1=C(C)C=2N=C(C=3C(=NC(=CC=3)C(C)C)NC)C(CC)=NC=2N1CC1=CC=CC=C1 BUDHDLJHCYFGNX-UHFFFAOYSA-N 0.000 claims 1
- FTYWNDYCCNDEFZ-UHFFFAOYSA-N 3-(1-butan-2-yl-6-ethyl-3-methylpyrazolo[3,4-b]pyrazin-5-yl)-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CCC=1N=C2N(C(C)CC)N=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NC FTYWNDYCCNDEFZ-UHFFFAOYSA-N 0.000 claims 1
- ZMZJUIOHRNZPIQ-UHFFFAOYSA-N 3-(3,6-dimethyl-1-pentan-3-ylpyrazolo[3,4-b]pyrazin-5-yl)-n,n-dimethyl-6-propan-2-ylpyridin-2-amine Chemical class CC=1N=C2N(C(CC)CC)N=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1N(C)C ZMZJUIOHRNZPIQ-UHFFFAOYSA-N 0.000 claims 1
- DRTUJIXMLFTIHD-UHFFFAOYSA-N 3-(3,6-dimethyl-1-pentan-3-ylpyrazolo[3,4-b]pyrazin-5-yl)-n-methyl-6-propan-2-ylpyridin-2-amine Chemical class CC=1N=C2N(C(CC)CC)N=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NC DRTUJIXMLFTIHD-UHFFFAOYSA-N 0.000 claims 1
- AVJYVWPFLPYXRZ-UHFFFAOYSA-N 3-(6-ethyl-3-methyl-1-pentan-3-ylpyrazolo[3,4-b]pyrazin-5-yl)-n,n-dimethyl-6-propan-2-ylpyridin-2-amine Chemical compound CCC=1N=C2N(C(CC)CC)N=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1N(C)C AVJYVWPFLPYXRZ-UHFFFAOYSA-N 0.000 claims 1
- OZMVZEAPSPBOTR-UHFFFAOYSA-N 3-(6-ethyl-3-methyl-1-pentan-3-ylpyrazolo[3,4-b]pyrazin-5-yl)-n-(2-methoxyethyl)-6-propan-2-ylpyridin-2-amine Chemical compound CCC=1N=C2N(C(CC)CC)N=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NCCOC OZMVZEAPSPBOTR-UHFFFAOYSA-N 0.000 claims 1
- PUNCRTBOJKCWFC-UHFFFAOYSA-N 3-(6-ethyl-3-methyl-1-pentan-3-ylpyrazolo[3,4-b]pyrazin-5-yl)-n-(3-piperidin-1-ylpropyl)-6-propan-2-ylpyridin-2-amine Chemical compound CCC=1N=C2N(C(CC)CC)N=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NCCCN1CCCCC1 PUNCRTBOJKCWFC-UHFFFAOYSA-N 0.000 claims 1
- TWVVREXPWXIGFH-UHFFFAOYSA-N 3-(6-ethyl-3-methyl-1-pentan-3-ylpyrazolo[3,4-b]pyrazin-5-yl)-n-(oxolan-2-ylmethyl)-6-propan-2-ylpyridin-2-amine Chemical compound CCC=1N=C2N(C(CC)CC)N=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NCC1CCCO1 TWVVREXPWXIGFH-UHFFFAOYSA-N 0.000 claims 1
- KKPHSQPAGFZWBS-UHFFFAOYSA-N 3-(6-ethyl-3-methyl-1-pentan-3-ylpyrazolo[3,4-b]pyrazin-5-yl)-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CCC=1N=C2N(C(CC)CC)N=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NC KKPHSQPAGFZWBS-UHFFFAOYSA-N 0.000 claims 1
- XWAOLOLIBVUZCF-UHFFFAOYSA-N 3-[1-(1,1-diethoxybutan-2-yl)-6-ethyl-3-methylpyrazolo[3,4-b]pyrazin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CCC=1N=C2N(C(CC)C(OCC)OCC)N=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NC XWAOLOLIBVUZCF-UHFFFAOYSA-N 0.000 claims 1
- RSVRQSRFOBRMHK-UHFFFAOYSA-N 3-[1-(1,3-dimethoxypropan-2-yl)-6-ethyl-3-methylpyrazolo[3,4-b]pyrazin-5-yl]-n,n-dimethyl-6-propan-2-ylpyridin-2-amine Chemical compound CCC1=NC=2N(C(COC)COC)N=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1N(C)C RSVRQSRFOBRMHK-UHFFFAOYSA-N 0.000 claims 1
- PZJJWCLPVPMFRF-UHFFFAOYSA-N 3-[1-(1,3-dimethoxypropan-2-yl)-6-ethyl-3-methylpyrazolo[3,4-b]pyrazin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CCC1=NC=2N(C(COC)COC)N=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1NC PZJJWCLPVPMFRF-UHFFFAOYSA-N 0.000 claims 1
- CIMAAIMUGNKMAO-UHFFFAOYSA-N 3-[6-ethyl-1-(1-methoxybutan-2-yl)-3-methylpyrazolo[3,4-b]pyrazin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CCC=1N=C2N(C(COC)CC)N=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NC CIMAAIMUGNKMAO-UHFFFAOYSA-N 0.000 claims 1
- FFCKMZDPHGHDRN-UHFFFAOYSA-N 3-[6-ethyl-1-(1-methoxypropan-2-yl)-3-methylpyrazolo[3,4-b]pyrazin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CCC1=NC=2N(C(C)COC)N=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1NC FFCKMZDPHGHDRN-UHFFFAOYSA-N 0.000 claims 1
- YLWZRYDNZWRUQD-UHFFFAOYSA-N 3-[6-ethyl-3-methyl-1-(1-morpholin-4-ylbutan-2-yl)pyrazolo[3,4-b]pyrazin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound N1=C(C)C2=NC(C=3C(=NC(=CC=3)C(C)C)NC)=C(CC)N=C2N1C(CC)CN1CCOCC1 YLWZRYDNZWRUQD-UHFFFAOYSA-N 0.000 claims 1
- SAQMOSWKTMUTJQ-UHFFFAOYSA-N 4-[2-[6-ethyl-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3-methylpyrazolo[3,4-b]pyrazin-1-yl]-3-methoxypropyl]morpholine Chemical compound CCC1=NC=2N(C(COC)CN3CCOCC3)N=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1OC SAQMOSWKTMUTJQ-UHFFFAOYSA-N 0.000 claims 1
- KPRZMBJIBABYFU-UHFFFAOYSA-N 4-[3-(3,6-dimethyl-1-pentan-3-ylpyrazolo[3,4-b]pyrazin-5-yl)-6-propan-2-ylpyridin-2-yl]morpholine Chemical compound CC=1N=C2N(C(CC)CC)N=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1N1CCOCC1 KPRZMBJIBABYFU-UHFFFAOYSA-N 0.000 claims 1
- FYNJTFSJMRNADD-UHFFFAOYSA-N 5-(1,5-dimethyl-3-pentan-3-ylpyrazolo[3,4-b]pyridin-6-yl)-3-methoxy-6-methyl-n-pentan-3-ylpyrazin-2-amine Chemical compound N1=C(OC)C(NC(CC)CC)=NC(C)=C1C(C(=C1)C)=NC2=C1C(C(CC)CC)=NN2C FYNJTFSJMRNADD-UHFFFAOYSA-N 0.000 claims 1
- UOPJLQPVWYXERQ-UHFFFAOYSA-N 5-(2-chloro-4-methoxyphenyl)-6-ethyl-3-methyl-1-pentan-3-ylpyrazolo[3,4-b]pyrazine Chemical compound CCC=1N=C2N(C(CC)CC)N=C(C)C2=NC=1C1=CC=C(OC)C=C1Cl UOPJLQPVWYXERQ-UHFFFAOYSA-N 0.000 claims 1
- NYQIDMBKPDTHQM-UHFFFAOYSA-N 5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethyl-1-pentan-3-ylpyrazolo[3,4-b]pyrazine Chemical compound CC=1N=C2N(C(CC)CC)N=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC NYQIDMBKPDTHQM-UHFFFAOYSA-N 0.000 claims 1
- XDWUNABFOGIJOS-UHFFFAOYSA-N 5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethyl-1-propan-2-ylpyrazolo[3,4-b]pyrazine Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=N1)C)=NC2=C1N(C(C)C)N=C2C XDWUNABFOGIJOS-UHFFFAOYSA-N 0.000 claims 1
- LOMFKMCPDJJTGM-UHFFFAOYSA-N 5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-n,3-dimethyl-1-pentan-3-ylpyrazolo[3,4-b]pyrazin-6-amine Chemical compound CNC=1N=C2N(C(CC)CC)N=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC LOMFKMCPDJJTGM-UHFFFAOYSA-N 0.000 claims 1
- CSROFRAFISMKIB-UHFFFAOYSA-N 5-(3,6-dimethyl-1-pentan-3-ylpyrazolo[3,4-b]pyrazin-5-yl)-4-methoxy-n,n-dimethylpyridin-2-amine Chemical class CC=1N=C2N(C(CC)CC)N=C(C)C2=NC=1C1=CN=C(N(C)C)C=C1OC CSROFRAFISMKIB-UHFFFAOYSA-N 0.000 claims 1
- AULRDTJMIJDNIP-UHFFFAOYSA-N 5-(3,6-dimethyl-1-pentan-3-ylpyrazolo[3,4-b]pyrazin-5-yl)-n,n,4-triethylpyridin-2-amine Chemical class CC=1N=C2N(C(CC)CC)N=C(C)C2=NC=1C1=CN=C(N(CC)CC)C=C1CC AULRDTJMIJDNIP-UHFFFAOYSA-N 0.000 claims 1
- DYRLLDGYNJSVQQ-UHFFFAOYSA-N 5-(3,6-dimethyl-1-pentan-3-ylpyrazolo[3,4-b]pyrazin-5-yl)-n,n-dimethyl-4-propan-2-yloxypyridin-2-amine Chemical class CC=1N=C2N(C(CC)CC)N=C(C)C2=NC=1C1=CN=C(N(C)C)C=C1OC(C)C DYRLLDGYNJSVQQ-UHFFFAOYSA-N 0.000 claims 1
- IDTORXIZLZZSAQ-UHFFFAOYSA-N 5-(5-ethyl-1-methyl-3-propan-2-ylpyrazolo[3,4-b]pyridin-6-yl)-3-methoxy-6-methyl-n-pentan-3-ylpyrazin-2-amine Chemical compound N1=C(OC)C(NC(CC)CC)=NC(C)=C1C(C(=C1)CC)=NC2=C1C(C(C)C)=NN2C IDTORXIZLZZSAQ-UHFFFAOYSA-N 0.000 claims 1
- CTPZWLJHXYJILO-UHFFFAOYSA-N 5-(6-ethyl-3-methyl-1-pentan-3-ylpyrazolo[3,4-b]pyrazin-5-yl)-n,n-dimethyl-4-propan-2-yloxypyridin-2-amine Chemical compound CCC=1N=C2N(C(CC)CC)N=C(C)C2=NC=1C1=CN=C(N(C)C)C=C1OC(C)C CTPZWLJHXYJILO-UHFFFAOYSA-N 0.000 claims 1
- RITBHLKMBVDJPA-UHFFFAOYSA-N 5-[2-(azetidin-1-yl)-6-propan-2-ylpyridin-3-yl]-3,6-dimethyl-1-pentan-3-ylpyrazolo[3,4-b]pyrazine Chemical compound CC=1N=C2N(C(CC)CC)N=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1N1CCC1 RITBHLKMBVDJPA-UHFFFAOYSA-N 0.000 claims 1
- QWNWRFNUXKHGAA-UHFFFAOYSA-N 5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethyl-1-pentan-3-ylpyrazolo[3,4-b]pyrazine Chemical compound CC=1N=C2N(C(CC)CC)N=C(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC QWNWRFNUXKHGAA-UHFFFAOYSA-N 0.000 claims 1
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- 2004-09-03 WO PCT/US2004/028663 patent/WO2005028480A2/en not_active Ceased
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- 2004-09-03 US US10/933,700 patent/US20050070542A1/en not_active Abandoned
- 2004-09-03 AU AU2004274403A patent/AU2004274403A1/en not_active Abandoned
- 2004-09-03 JP JP2006525454A patent/JP2007504243A/ja active Pending
- 2004-09-03 EP EP04788563A patent/EP1675858A2/en not_active Withdrawn
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