JP2007504243A - ５−アリール−ピラゾロ［４，３−ｄ］ピリミジン類、ピリジン類、ピラジン類及び関連化合物 - Google Patents

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Publication number

JP2007504243A

JP2007504243A JP2006525454A JP2006525454A JP2007504243A JP 2007504243 A JP2007504243 A JP 2007504243A JP 2006525454 A JP2006525454 A JP 2006525454A JP 2006525454 A JP2006525454 A JP 2006525454A JP 2007504243 A JP2007504243 A JP 2007504243A

Authority

JP

Japan

Prior art keywords

alkyl

amino

substituted

alkoxy

mono

Prior art date

2003-09-03

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.)

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 346
• 150000003230 pyrimidines Chemical class 0.000 title abstract description 9
• 150000003216 pyrazines Chemical class 0.000 title 1
• 150000003222 pyridines Chemical class 0.000 title 1
• 238000000034 method Methods 0.000 claims abstract description 138
• 108010056643 Corticotropin-Releasing Hormone Receptors Proteins 0.000 claims abstract description 58
• 230000027455 binding Effects 0.000 claims abstract description 41
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 36
• 208000035475 disorder Diseases 0.000 claims abstract description 24
• 108091005471 CRHR1 Proteins 0.000 claims abstract description 14
• 208000019901 Anxiety disease Diseases 0.000 claims abstract description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
• 208000030814 Eating disease Diseases 0.000 claims abstract description 10
• 208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 10
• 235000014632 disordered eating Nutrition 0.000 claims abstract description 10
• -1 tri-substituted phenyl Chemical group 0.000 claims description 485
• 229910052736 halogen Inorganic materials 0.000 claims description 195
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 188
• 150000002367 halogens Chemical class 0.000 claims description 171
• 125000000217 alkyl group Chemical group 0.000 claims description 166
• 229930195733 hydrocarbon Natural products 0.000 claims description 151
• 150000003839 salts Chemical class 0.000 claims description 146
• 125000001424 substituent group Chemical group 0.000 claims description 134
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 125
• 229910052739 hydrogen Inorganic materials 0.000 claims description 104
• 239000001257 hydrogen Substances 0.000 claims description 103
• 239000000203 mixture Substances 0.000 claims description 76
• 150000002431 hydrogen Chemical class 0.000 claims description 71
• 238000012360 testing method Methods 0.000 claims description 66
• 239000004215 Carbon black (E152) Substances 0.000 claims description 63
• 239000000243 solution Substances 0.000 claims description 63
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 62
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 60
• 125000001072 heteroaryl group Chemical class 0.000 claims description 56
• 229910052760 oxygen Inorganic materials 0.000 claims description 56
• 125000004076 pyridyl group Chemical group 0.000 claims description 55
• 150000002430 hydrocarbons Chemical class 0.000 claims description 53
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
• 125000003282 alkyl amino group Chemical group 0.000 claims description 51
• 125000005843 halogen group Chemical group 0.000 claims description 50
• 229910052757 nitrogen Inorganic materials 0.000 claims description 50
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 48
• 125000004043 oxo group Chemical group O=* 0.000 claims description 48
• 210000004027 cell Anatomy 0.000 claims description 45
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 41
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 40
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 40
• 229910052717 sulfur Inorganic materials 0.000 claims description 40
• 125000003118 aryl group Chemical group 0.000 claims description 38
• 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 description 38
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 36
• 125000003545 alkoxy group Chemical group 0.000 claims description 36
• 238000002360 preparation method Methods 0.000 claims description 35
• 125000004432 carbon atom Chemical group C* 0.000 claims description 34
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 33
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 31
• 238000000338 in vitro Methods 0.000 claims description 29
• 229920006395 saturated elastomer Polymers 0.000 claims description 27
• 230000000694 effects Effects 0.000 claims description 26
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 24
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 24
• 125000002757 morpholinyl group Chemical group 0.000 claims description 24
• 125000004193 piperazinyl group Chemical group 0.000 claims description 24
• 125000003386 piperidinyl group Chemical group 0.000 claims description 24
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 24
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 23
• 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 23
• 125000005842 heteroatom Chemical group 0.000 claims description 23
• 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims description 22
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 22
• 125000002393 azetidinyl group Chemical group 0.000 claims description 21
• 125000005047 dihydroimidazolyl group Chemical group N1(CNC=C1)* 0.000 claims description 21
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 21
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 21
• 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 description 20
• 229910052799 carbon Inorganic materials 0.000 claims description 20
• 125000001188 haloalkyl group Chemical group 0.000 claims description 19
• 239000001301 oxygen Substances 0.000 claims description 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 description 19
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 18
• 125000001544 thienyl group Chemical group 0.000 claims description 18
• 125000002541 furyl group Chemical group 0.000 claims description 17
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 16
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 16
• 125000002971 oxazolyl group Chemical group 0.000 claims description 16
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 16
• 125000000335 thiazolyl group Chemical group 0.000 claims description 16
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
• 125000004429 atom Chemical group 0.000 claims description 15
• 125000000623 heterocyclic group Chemical group 0.000 claims description 15
• 241001465754 Metazoa Species 0.000 claims description 13
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 13
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 12
• 125000001425 triazolyl group Chemical group 0.000 claims description 12
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
• 125000004414 alkyl thio group Chemical group 0.000 claims description 11
• 125000004122 cyclic group Chemical group 0.000 claims description 11
• 150000003462 sulfoxides Chemical class 0.000 claims description 11
• 108010052164 Sodium Channels Proteins 0.000 claims description 10
• 102000018674 Sodium Channels Human genes 0.000 claims description 10
• 125000006165 cyclic alkyl group Chemical group 0.000 claims description 10
• 201000010099 disease Diseases 0.000 claims description 10
• GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 10
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 10
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 10
• 239000011593 sulfur Substances 0.000 claims description 10
• 125000001589 carboacyl group Chemical group 0.000 claims description 9
• 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims description 9
• 238000001727 in vivo Methods 0.000 claims description 9
• 150000003457 sulfones Chemical class 0.000 claims description 9
• 125000005942 tetrahydropyridyl group Chemical group 0.000 claims description 9
• 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 description 8
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 8
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
• 238000006467 substitution reaction Methods 0.000 claims description 8
• 229910052727 yttrium Inorganic materials 0.000 claims description 7
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
• 125000005432 dialkylcarboxamide group Chemical group 0.000 claims description 6
• 125000006413 ring segment Chemical group 0.000 claims description 6
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 6
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 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 description 4
• SCFLYACWYMJURL-UHFFFAOYSA-N 5-[2-methoxy-4-(trifluoromethoxy)phenyl]-6-methyl-1-pentan-3-ylpyrazolo[3,4-b]pyrazine Chemical compound CC=1N=C2N(C(CC)CC)N=CC2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC SCFLYACWYMJURL-UHFFFAOYSA-N 0.000 claims description 4
• BRZNXTNBNXQMGU-UHFFFAOYSA-N 6-ethyl-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-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(C(C)C)N=C1OC BRZNXTNBNXQMGU-UHFFFAOYSA-N 0.000 claims description 4
• CHEDQUJEAKPKCQ-UHFFFAOYSA-N 6-ethyl-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3-methyl-1-propan-2-ylpyrazolo[3,4-b]pyrazine Chemical compound CCC1=NC=2N(C(C)C)N=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1OC CHEDQUJEAKPKCQ-UHFFFAOYSA-N 0.000 claims description 4
• 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 4
• 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 description 4
• 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 4
• 125000005945 imidazopyridyl group Chemical group 0.000 claims description 4
• 238000001525 receptor binding assay Methods 0.000 claims description 4
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• YTCLZHORLMANMB-UHFFFAOYSA-N 5-ethyl-6-[2-methoxy-4-(trifluoromethoxy)phenyl]-1-methyl-3-pentan-3-ylpyrazolo[3,4-b]pyridine Chemical compound CCC=1C=C2C(C(CC)CC)=NN(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC YTCLZHORLMANMB-UHFFFAOYSA-N 0.000 claims description 3
• HYURDKIHMQOXOZ-UHFFFAOYSA-N 6-methoxy-5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3-methyl-1-pentan-3-ylpyrazolo[3,4-b]pyrazine Chemical compound COC=1N=C2N(C(CC)CC)N=C(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC HYURDKIHMQOXOZ-UHFFFAOYSA-N 0.000 claims description 3
• 208000000103 Anorexia Nervosa Diseases 0.000 claims description 3
• 208000020925 Bipolar disease Diseases 0.000 claims description 3
• 206010006550 Bulimia nervosa Diseases 0.000 claims description 3
• 208000008589 Obesity Diseases 0.000 claims description 3
• 208000028683 bipolar I disease Diseases 0.000 claims description 3
• 238000001514 detection method Methods 0.000 claims description 3
• UGPBBCNSDNHARL-UHFFFAOYSA-N n-[2-[6-ethyl-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3-methylpyrazolo[3,4-b]pyrazin-1-yl]-3-methoxypropyl]cyclobutanamine Chemical compound CCC1=NC=2N(C(CNC3CCC3)COC)N=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1OC UGPBBCNSDNHARL-UHFFFAOYSA-N 0.000 claims description 3
• SPVZHHINVCWERL-UHFFFAOYSA-N n-[2-[6-ethyl-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3-methylpyrazolo[3,4-b]pyrazin-1-yl]propyl]cyclobutanamine Chemical compound CCC1=NC=2N(C(C)CNC3CCC3)N=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1OC SPVZHHINVCWERL-UHFFFAOYSA-N 0.000 claims description 3
• 235000020824 obesity Nutrition 0.000 claims description 3
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
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