JP5671236B2 - ホスホジエステラーゼ阻害剤としてのピラゾロ（３，４−ｂ）ピリジン誘導体 - Google Patents

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Publication number

JP5671236B2

JP5671236B2 JP2009553263A JP2009553263A JP5671236B2 JP 5671236 B2 JP5671236 B2 JP 5671236B2 JP 2009553263 A JP2009553263 A JP 2009553263A JP 2009553263 A JP2009553263 A JP 2009553263A JP 5671236 B2 JP5671236 B2 JP 5671236B2

Authority

JP

Japan

Prior art keywords

compound

pyrazolo

oxa

ethyl

azaspiro

Prior art date

2007-03-14

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.)

Expired - Fee Related

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• 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 title description 2
• 239000002571 phosphodiesterase inhibitor Substances 0.000 title description 2
• 150000005230 pyrazolo[3,4-b]pyridines Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims description 1704
• -1 1-oxa-2-azaspiro [4.4] non-2-en-3-yl Chemical group 0.000 claims description 429
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 152
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 137
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 135
• 125000000217 alkyl group Chemical group 0.000 claims description 98
• 238000002360 preparation method Methods 0.000 claims description 67
• 238000006243 chemical reaction Methods 0.000 claims description 63
• NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Natural products OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 58
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 57
• 229910052736 halogen Inorganic materials 0.000 claims description 48
• 125000003118 aryl group Chemical group 0.000 claims description 45
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 42
• 239000001257 hydrogen Substances 0.000 claims description 42
• 229910052739 hydrogen Inorganic materials 0.000 claims description 42
• 125000000623 heterocyclic group Chemical group 0.000 claims description 40
• NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims description 39
• 229960004979 fampridine Drugs 0.000 claims description 37
• 125000001072 heteroaryl group Chemical group 0.000 claims description 36
• 238000000034 method Methods 0.000 claims description 36
• VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims description 35
• 150000002367 halogens Chemical class 0.000 claims description 35
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 34
• 150000001412 amines Chemical class 0.000 claims description 29
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 26
• 125000004432 carbon atom Chemical group C* 0.000 claims description 25
• 150000003839 salts Chemical class 0.000 claims description 24
• 238000004519 manufacturing process Methods 0.000 claims description 23
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 21
• 125000003545 alkoxy group Chemical group 0.000 claims description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 18
• 239000012453 solvate Substances 0.000 claims description 17
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 16
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 14
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 125000006239 protecting group Chemical group 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 229910052717 sulfur Inorganic materials 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 125000004429 atom Chemical group 0.000 claims description 10
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 10
• 230000007062 hydrolysis Effects 0.000 claims description 10
• 238000006460 hydrolysis reaction Methods 0.000 claims description 10
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 10
• 229920006395 saturated elastomer Polymers 0.000 claims description 10
• 150000001204 N-oxides Chemical class 0.000 claims description 9
• 238000010438 heat treatment Methods 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• LFFBLXGLSVUNCU-UHFFFAOYSA-N 3-[4-(cyclohexylamino)-1-ethylpyrazolo[3,4-b]pyridin-5-yl]-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carboxylic acid Chemical compound N=1OC2(CCC(CC2)C(O)=O)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCCCC1 LFFBLXGLSVUNCU-UHFFFAOYSA-N 0.000 claims description 7
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 7
• ZNFZKLZYIWAINB-UHFFFAOYSA-N 1-ethyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)-n-(2h-tetrazol-5-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCCCC2)CC=1C1=CN=C2N(CC)N=CC2=C1NC=1N=NNN=1 ZNFZKLZYIWAINB-UHFFFAOYSA-N 0.000 claims description 6
• MLKUXEUXLXZRIW-UHFFFAOYSA-N 1-ethyl-5-(5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)-n-(2h-tetrazol-5-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCC2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1=NN=NN1 MLKUXEUXLXZRIW-UHFFFAOYSA-N 0.000 claims description 6
• WMLAXUQNIMKNOY-UHFFFAOYSA-N 1-ethyl-n-(oxan-4-yl)-5-[8-(2h-tetrazol-5-yl)-1-oxa-2-azaspiro[4.5]dec-2-en-3-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCC(CC2)C=2NN=NN=2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 WMLAXUQNIMKNOY-UHFFFAOYSA-N 0.000 claims description 6
• JEQLNHRWXLRVHS-UHFFFAOYSA-N 1-oxa-7-azaspiro[3.4]oct-6-ene-2-carboxylic acid Chemical compound O1C(C(=O)O)CC11CN=CC1 JEQLNHRWXLRVHS-UHFFFAOYSA-N 0.000 claims description 6
• FVOWSQAKARXCSJ-UHFFFAOYSA-N 7-[4-(cyclohexylamino)-1-ethylpyrazolo[3,4-b]pyridin-5-yl]-5-oxa-6-azaspiro[3.4]oct-6-ene-2-carboxamide Chemical compound N=1OC2(CC(C2)C(N)=O)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCCCC1 FVOWSQAKARXCSJ-UHFFFAOYSA-N 0.000 claims description 6
• ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 6
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 6
• TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims description 6
• ZIQKZQQAOSZFCA-UHFFFAOYSA-N n-cyclohexyl-1-ethyl-5-[2-(2h-tetrazol-5-yl)-5-oxa-6-azaspiro[3.4]oct-6-en-7-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CC(C2)C=2NN=NN=2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCCCC1 ZIQKZQQAOSZFCA-UHFFFAOYSA-N 0.000 claims description 6
• 229910052698 phosphorus Inorganic materials 0.000 claims description 6
• 239000011574 phosphorus Substances 0.000 claims description 6
• DEEWYTJMOOJNBK-UHFFFAOYSA-N 1-ethyl-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)-n-(2h-tetrazol-5-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCCC2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1=NN=NN1 DEEWYTJMOOJNBK-UHFFFAOYSA-N 0.000 claims description 5
• JFNPQHWGYOMASF-UHFFFAOYSA-N 2-methyloct-6-enamide Chemical compound CC(CCCC=CC)C(=O)N JFNPQHWGYOMASF-UHFFFAOYSA-N 0.000 claims description 5
• PZFJUACXAVTYCR-UHFFFAOYSA-N 3-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1-oxa-2-azaspiro[4.5]dec-2-en-8-ol Chemical compound N=1OC2(CCC(O)CC2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 PZFJUACXAVTYCR-UHFFFAOYSA-N 0.000 claims description 5
• YQHLBGCEOFVNRI-UHFFFAOYSA-N 3-[4-(cyclohexylamino)-1-ethylpyrazolo[3,4-b]pyridin-5-yl]-1-oxa-2-azaspiro[4.5]dec-2-en-8-ol Chemical compound N=1OC2(CCC(O)CC2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCCCC1 YQHLBGCEOFVNRI-UHFFFAOYSA-N 0.000 claims description 5
• GNWLJMQPQWNRAW-UHFFFAOYSA-N 3-[4-(cyclohexylamino)-1-ethylpyrazolo[3,4-b]pyridin-5-yl]-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carboxamide Chemical compound N=1OC2(CCC(CC2)C(N)=O)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCCCC1 GNWLJMQPQWNRAW-UHFFFAOYSA-N 0.000 claims description 5
• DQXSINZAPNJLPW-UHFFFAOYSA-N 7-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-5-oxa-6-azaspiro[3.4]oct-6-en-2-ol Chemical compound N=1OC2(CC(O)C2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 DQXSINZAPNJLPW-UHFFFAOYSA-N 0.000 claims description 5
• RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 claims description 5
• 239000001099 ammonium carbonate Substances 0.000 claims description 5
• 235000012501 ammonium carbonate Nutrition 0.000 claims description 5
• PVJUEQVHBIFETG-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]-5-(5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound C1=CC(OC)=CC=C1CN1C2=NC=C(C=3CC4(CCC4)ON=3)C(NC3CCOCC3)=C2C=N1 PVJUEQVHBIFETG-UHFFFAOYSA-N 0.000 claims description 4
• JJISQWLMMLKYIE-UHFFFAOYSA-N 1-oxa-2-azaspiro[4.5]dec-2-ene-8-carboxylic acid Chemical compound C1CC(C(=O)O)CCC11ON=CC1 JJISQWLMMLKYIE-UHFFFAOYSA-N 0.000 claims description 4
• HZJBYJQUGDNCQI-UHFFFAOYSA-N 3-[4-(cyclohexylamino)-1-ethylpyrazolo[3,4-b]pyridin-5-yl]-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carbonitrile Chemical compound N=1OC2(CCC(CC2)C#N)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCCCC1 HZJBYJQUGDNCQI-UHFFFAOYSA-N 0.000 claims description 4
• LBQUIYPYQXKGEC-UHFFFAOYSA-N 7-[4-(cyclohexylamino)-1-ethylpyrazolo[3,4-b]pyridin-5-yl]-5-oxa-6-azaspiro[3.4]oct-6-ene-2-carbonitrile Chemical compound N=1OC2(CC(C2)C#N)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCCCC1 LBQUIYPYQXKGEC-UHFFFAOYSA-N 0.000 claims description 4
• KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 4
• 238000003328 mesylation reaction Methods 0.000 claims description 4
• BDHHZQLMLPTXGC-UHFFFAOYSA-N n-cyclohexyl-1-ethyl-5-(1-oxa-2,8-diazaspiro[4.5]dec-2-en-3-yl)pyrazolo[3,4-b]pyridin-4-amine;hydrochloride Chemical compound Cl.N=1OC2(CCNCC2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCCCC1 BDHHZQLMLPTXGC-UHFFFAOYSA-N 0.000 claims description 4
• PZHUBHQXCJHHLB-UHFFFAOYSA-N 1-(cyclopropylmethyl)-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N1=CC2=C(NC3CCOCC3)C(C=3CC4(CCCC4)ON=3)=CN=C2N1CC1CC1 PZHUBHQXCJHHLB-UHFFFAOYSA-N 0.000 claims description 3
• SBGGPVSBKJWNLG-UHFFFAOYSA-N 1-(cyclopropylmethyl)-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N1=CC2=C(NC3CCOCC3)C(C=3CC4(ON=3)CCCCC4)=CN=C2N1CC1CC1 SBGGPVSBKJWNLG-UHFFFAOYSA-N 0.000 claims description 3
• IGMPWTRPXGOCHS-UHFFFAOYSA-N 1-(cyclopropylmethyl)-5-(5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N1=CC2=C(NC3CCOCC3)C(C=3CC4(CCC4)ON=3)=CN=C2N1CC1CC1 IGMPWTRPXGOCHS-UHFFFAOYSA-N 0.000 claims description 3
• GYFPTAYEBLSOGG-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound C1=CC(OC)=CC=C1CN1C2=NC=C(C=3CC4(CCCC4)ON=3)C(NC3CCOCC3)=C2C=N1 GYFPTAYEBLSOGG-UHFFFAOYSA-N 0.000 claims description 3
• LXCJOEZUGGCDIV-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound C1=CC(OC)=CC=C1CN1C2=NC=C(C=3CC4(ON=3)CCCCC4)C(NC3CCOCC3)=C2C=N1 LXCJOEZUGGCDIV-UHFFFAOYSA-N 0.000 claims description 3
• HAVHTLDFDUYFRU-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]-n-(oxan-4-yl)-5-(2-phenylmethoxy-5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound C1=CC(OC)=CC=C1CN1C2=NC=C(C=3CC4(CC(C4)OCC=4C=CC=CC=4)ON=3)C(NC3CCOCC3)=C2C=N1 HAVHTLDFDUYFRU-UHFFFAOYSA-N 0.000 claims description 3
• FXWCIVCUNGBMOK-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]-n-(oxan-4-yl)-5-[2-(phenylmethoxymethyl)-5-oxa-6-azaspiro[3.4]oct-6-en-7-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound C1=CC(OC)=CC=C1CN1C2=NC=C(C=3CC4(CC(COCC=5C=CC=CC=5)C4)ON=3)C(NC3CCOCC3)=C2C=N1 FXWCIVCUNGBMOK-UHFFFAOYSA-N 0.000 claims description 3
• AXZYIQDVDKWBGB-UHFFFAOYSA-N 1-[3-[4-(cyclohexylamino)-1-ethylpyrazolo[3,4-b]pyridin-5-yl]-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]ethanone Chemical compound N=1OC2(CCN(CC2)C(C)=O)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCCCC1 AXZYIQDVDKWBGB-UHFFFAOYSA-N 0.000 claims description 3
• XQRAHBXMZNTQMW-UHFFFAOYSA-N 1-butyl-5-(5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCC2)CC=1C1=CN=C2N(CCCC)N=CC2=C1NC1CCOCC1 XQRAHBXMZNTQMW-UHFFFAOYSA-N 0.000 claims description 3
• MENNUEDHXUHZOW-UHFFFAOYSA-N 1-cyclopentyl-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound C1CCCC1N1C2=NC=C(C=3CC4(CCCC4)ON=3)C(NC3CCOCC3)=C2C=N1 MENNUEDHXUHZOW-UHFFFAOYSA-N 0.000 claims description 3
• YMIYGXSCWRBZGA-UHFFFAOYSA-N 1-cyclopentyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound C1CCCC1N1C2=NC=C(C=3CC4(ON=3)CCCCC4)C(NC3CCOCC3)=C2C=N1 YMIYGXSCWRBZGA-UHFFFAOYSA-N 0.000 claims description 3
• CBJXSYDXPOWJOP-UHFFFAOYSA-N 1-ethyl-3-methyl-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCCC2)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CCOCC1 CBJXSYDXPOWJOP-UHFFFAOYSA-N 0.000 claims description 3
• JUYLBPKKTFJJIS-UHFFFAOYSA-N 1-ethyl-3-methyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCCCC2)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CCOCC1 JUYLBPKKTFJJIS-UHFFFAOYSA-N 0.000 claims description 3
• ZGDOJPHJVMSVIC-UHFFFAOYSA-N 1-ethyl-3-methyl-5-(5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCC2)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CCOCC1 ZGDOJPHJVMSVIC-UHFFFAOYSA-N 0.000 claims description 3
• PHVPHRJULHFNEF-UHFFFAOYSA-N 1-ethyl-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)-n-(1,2,4-triazin-3-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCCC2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1=NC=CN=N1 PHVPHRJULHFNEF-UHFFFAOYSA-N 0.000 claims description 3
• ASMWLGBIOREDJQ-UHFFFAOYSA-N 1-ethyl-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)-n-(1,2,4-triazin-5-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCCC2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1=CN=NC=N1 ASMWLGBIOREDJQ-UHFFFAOYSA-N 0.000 claims description 3
• UURAWHVLDGPHEK-UHFFFAOYSA-N 1-ethyl-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)-n-(1,2,4-triazol-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCCC2)CC=1C1=CN=C2N(CC)N=CC2=C1NN1C=NN=C1 UURAWHVLDGPHEK-UHFFFAOYSA-N 0.000 claims description 3
• UFKSYNRZBZDMGM-UHFFFAOYSA-N 1-ethyl-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCCC2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(C)C)CC1 UFKSYNRZBZDMGM-UHFFFAOYSA-N 0.000 claims description 3
• HKDBWBKWDRPSPJ-UHFFFAOYSA-N 1-ethyl-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCCC2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 HKDBWBKWDRPSPJ-UHFFFAOYSA-N 0.000 claims description 3
• ZZLNQJZHTPLNJU-UHFFFAOYSA-N 1-ethyl-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)-n-piperidin-4-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCCC2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCNCC1 ZZLNQJZHTPLNJU-UHFFFAOYSA-N 0.000 claims description 3
• CKTXTEHCGBRNPG-UHFFFAOYSA-N 1-ethyl-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)-n-pyrazin-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCCC2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1=CN=CC=N1 CKTXTEHCGBRNPG-UHFFFAOYSA-N 0.000 claims description 3
• WEBBKLMVBKDTMU-UHFFFAOYSA-N 1-ethyl-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)-n-pyridin-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCCC2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1=CC=CC=N1 WEBBKLMVBKDTMU-UHFFFAOYSA-N 0.000 claims description 3
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• HLDGIASLLBAGBM-UHFFFAOYSA-N 3-[4-(cyclohexylamino)-1-ethylpyrazolo[3,4-b]pyridin-5-yl]-n-methyl-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carboxamide Chemical compound N=1OC2(CCC(CC2)C(=O)NC)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCCCC1 HLDGIASLLBAGBM-UHFFFAOYSA-N 0.000 claims description 3
• NTIZHSUHOCODBE-UHFFFAOYSA-N 3-[4-[(4-carboxycyclohexyl)amino]-1-ethyl-3-methylpyrazolo[3,4-b]pyridin-5-yl]-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carboxylic acid Chemical compound N=1OC2(CCC(CC2)C(O)=O)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CCC(C(O)=O)CC1 NTIZHSUHOCODBE-UHFFFAOYSA-N 0.000 claims description 3
• UCSDKOFCALOSHG-UHFFFAOYSA-N 3-[4-[(4-carboxycyclohexyl)amino]-1-ethylpyrazolo[3,4-b]pyridin-5-yl]-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carboxylic acid Chemical compound N=1OC2(CCC(CC2)C(O)=O)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCC(C(O)=O)CC1 UCSDKOFCALOSHG-UHFFFAOYSA-N 0.000 claims description 3
• ZYUFYQLRIBZSOR-UHFFFAOYSA-N 3-[[1-ethyl-3-methyl-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)pyrazolo[3,4-b]pyridin-4-yl]amino]cyclobutane-1-carboxylic acid Chemical compound N=1OC2(CCCC2)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CC(C(O)=O)C1 ZYUFYQLRIBZSOR-UHFFFAOYSA-N 0.000 claims description 3
• OFHRSRDKFXNNPG-UHFFFAOYSA-N 3-[[1-ethyl-3-methyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)pyrazolo[3,4-b]pyridin-4-yl]amino]cyclobutane-1-carboxylic acid Chemical compound N=1OC2(CCCCC2)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CC(C(O)=O)C1 OFHRSRDKFXNNPG-UHFFFAOYSA-N 0.000 claims description 3
• ZCYPGFUSSSQITG-UHFFFAOYSA-N 3-[[1-ethyl-3-methyl-5-(5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)pyrazolo[3,4-b]pyridin-4-yl]amino]cyclobutane-1-carboxylic acid Chemical compound N=1OC2(CCC2)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CC(C(O)=O)C1 ZCYPGFUSSSQITG-UHFFFAOYSA-N 0.000 claims description 3
• KWSLKXOMBGDOGL-UHFFFAOYSA-N 3-[[1-ethyl-3-methyl-5-[2-(propanoylamino)-5-oxa-6-azaspiro[3.4]oct-6-en-7-yl]pyrazolo[3,4-b]pyridin-4-yl]amino]cyclobutane-1-carboxylic acid Chemical compound C1C(NC(=O)CC)CC21ON=C(C=1C(=C3C(C)=NN(CC)C3=NC=1)NC1CC(C1)C(O)=O)C2 KWSLKXOMBGDOGL-UHFFFAOYSA-N 0.000 claims description 3
• LVIKXZDERZQDIU-UHFFFAOYSA-N 3-[[1-ethyl-5-(2-hydroxy-5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)-3-methylpyrazolo[3,4-b]pyridin-4-yl]amino]cyclobutane-1-carboxylic acid Chemical compound N=1OC2(CC(O)C2)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CC(C(O)=O)C1 LVIKXZDERZQDIU-UHFFFAOYSA-N 0.000 claims description 3
• IGHORDRHHKKZJZ-UHFFFAOYSA-N 3-[[1-ethyl-5-(8-hydroxy-1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)pyrazolo[3,4-b]pyridin-4-yl]amino]cyclobutane-1-carboxylic acid Chemical compound N=1OC2(CCC(O)CC2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CC(C(O)=O)C1 IGHORDRHHKKZJZ-UHFFFAOYSA-N 0.000 claims description 3
• KPDHDBQWOXOGPG-UHFFFAOYSA-N 3-[[5-(2-acetamido-5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)-1-ethyl-3-methylpyrazolo[3,4-b]pyridin-4-yl]amino]cyclobutane-1-carboxylic acid Chemical compound N=1OC2(CC(C2)NC(C)=O)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CC(C(O)=O)C1 KPDHDBQWOXOGPG-UHFFFAOYSA-N 0.000 claims description 3
• PGZJBOKWFLDJTE-UHFFFAOYSA-N 3-[[5-(2-amino-5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)-1-ethyl-3-methylpyrazolo[3,4-b]pyridin-4-yl]amino]cyclobutane-1-carboxylic acid Chemical compound N=1OC2(CC(N)C2)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CC(C(O)=O)C1 PGZJBOKWFLDJTE-UHFFFAOYSA-N 0.000 claims description 3
• KIXZJKIEIOOZQP-UHFFFAOYSA-N 3-[[5-(2-cyano-5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)-1-ethyl-3-methylpyrazolo[3,4-b]pyridin-4-yl]amino]cyclobutane-1-carboxylic acid Chemical compound N=1OC2(CC(C2)C#N)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CC(C(O)=O)C1 KIXZJKIEIOOZQP-UHFFFAOYSA-N 0.000 claims description 3
• SQVOMTDANVBANE-UHFFFAOYSA-N 3-[[5-(2-cyano-5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)-1-ethylpyrazolo[3,4-b]pyridin-4-yl]amino]cyclobutane-1-carboxylic acid Chemical compound N=1OC2(CC(C2)C#N)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CC(C(O)=O)C1 SQVOMTDANVBANE-UHFFFAOYSA-N 0.000 claims description 3
• ZBZDITMBKILWII-UHFFFAOYSA-N 3-[[5-(8-carbamoyl-1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)-1-ethylpyrazolo[3,4-b]pyridin-4-yl]amino]cyclobutane-1-carboxylic acid Chemical compound N=1OC2(CCC(CC2)C(N)=O)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CC(C(O)=O)C1 ZBZDITMBKILWII-UHFFFAOYSA-N 0.000 claims description 3
• XYAVXVGQZABIEL-UHFFFAOYSA-N 4-[[1-ethyl-3-methyl-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)pyrazolo[3,4-b]pyridin-4-yl]amino]cyclohexane-1-carboxylic acid Chemical compound N=1OC2(CCCC2)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CCC(C(O)=O)CC1 XYAVXVGQZABIEL-UHFFFAOYSA-N 0.000 claims description 3
• KQBIZFDBTIEOAK-UHFFFAOYSA-N 4-[[1-ethyl-3-methyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)pyrazolo[3,4-b]pyridin-4-yl]amino]cyclohexane-1-carboxylic acid Chemical compound N=1OC2(CCCCC2)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CCC(C(O)=O)CC1 KQBIZFDBTIEOAK-UHFFFAOYSA-N 0.000 claims description 3
• AWHQDYOFKUYUNZ-UHFFFAOYSA-N 4-[[1-ethyl-3-methyl-5-(5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)pyrazolo[3,4-b]pyridin-4-yl]amino]cyclohexane-1-carboxylic acid Chemical compound N=1OC2(CCC2)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CCC(C(O)=O)CC1 AWHQDYOFKUYUNZ-UHFFFAOYSA-N 0.000 claims description 3
• CBXUPDVQNWMCFS-UHFFFAOYSA-N 4-[[1-ethyl-3-methyl-5-[2-(methylcarbamoyl)-5-oxa-6-azaspiro[3.4]oct-6-en-7-yl]pyrazolo[3,4-b]pyridin-4-yl]amino]cyclohexane-1-carboxylic acid Chemical compound N=1OC2(CC(C2)C(=O)NC)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CCC(C(O)=O)CC1 CBXUPDVQNWMCFS-UHFFFAOYSA-N 0.000 claims description 3
• HTSPFHXLQCIYJT-UHFFFAOYSA-N 4-[[1-ethyl-3-methyl-5-[8-(methylcarbamoyl)-1-oxa-2-azaspiro[4.5]dec-2-en-3-yl]pyrazolo[3,4-b]pyridin-4-yl]amino]cyclohexane-1-carboxylic acid Chemical compound N=1OC2(CCC(CC2)C(=O)NC)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CCC(C(O)=O)CC1 HTSPFHXLQCIYJT-UHFFFAOYSA-N 0.000 claims description 3
• YSHJSIVBZYQTQO-UHFFFAOYSA-N 4-[[1-ethyl-3-methyl-5-[8-(propanoylamino)-1-oxa-2-azaspiro[4.5]dec-2-en-3-yl]pyrazolo[3,4-b]pyridin-4-yl]amino]cyclohexane-1-carboxylic acid Chemical compound C1CC(NC(=O)CC)CCC11ON=C(C=2C(=C3C(C)=NN(CC)C3=NC=2)NC2CCC(CC2)C(O)=O)C1 YSHJSIVBZYQTQO-UHFFFAOYSA-N 0.000 claims description 3
• UFHRLQXLDNCYQN-UHFFFAOYSA-N 4-[[1-ethyl-5-(2-hydroxy-5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)-3-methylpyrazolo[3,4-b]pyridin-4-yl]amino]cyclohexane-1-carboxylic acid Chemical compound N=1OC2(CC(O)C2)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CCC(C(O)=O)CC1 UFHRLQXLDNCYQN-UHFFFAOYSA-N 0.000 claims description 3
• UIBYFWAHRIBZPE-UHFFFAOYSA-N 4-[[1-ethyl-5-(8-hydroxy-1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)pyrazolo[3,4-b]pyridin-4-yl]amino]cyclohexane-1-carboxylic acid Chemical compound N=1OC2(CCC(O)CC2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCC(C(O)=O)CC1 UIBYFWAHRIBZPE-UHFFFAOYSA-N 0.000 claims description 3
• CGPLMIXJJVJOSU-UHFFFAOYSA-N 4-[[1-ethyl-5-(8-methoxy-1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)pyrazolo[3,4-b]pyridin-4-yl]amino]cyclohexane-1-carboxylic acid Chemical compound N=1OC2(CCC(CC2)OC)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCC(C(O)=O)CC1 CGPLMIXJJVJOSU-UHFFFAOYSA-N 0.000 claims description 3
• CBYBBQGERQVJQH-UHFFFAOYSA-N 4-[[1-ethyl-5-[2-(ethylcarbamoyl)-5-oxa-6-azaspiro[3.4]oct-6-en-7-yl]-3-methylpyrazolo[3,4-b]pyridin-4-yl]amino]cyclohexane-1-carboxylic acid Chemical compound C1C(C(=O)NCC)CC21ON=C(C=1C(=C3C(C)=NN(CC)C3=NC=1)NC1CCC(CC1)C(O)=O)C2 CBYBBQGERQVJQH-UHFFFAOYSA-N 0.000 claims description 3
• QDBNXZVVAGHTRE-UHFFFAOYSA-N 4-[[1-ethyl-5-[8-(ethylcarbamoyl)-1-oxa-2-azaspiro[4.5]dec-2-en-3-yl]-3-methylpyrazolo[3,4-b]pyridin-4-yl]amino]cyclohexane-1-carboxylic acid Chemical compound C1CC(C(=O)NCC)CCC11ON=C(C=2C(=C3C(C)=NN(CC)C3=NC=2)NC2CCC(CC2)C(O)=O)C1 QDBNXZVVAGHTRE-UHFFFAOYSA-N 0.000 claims description 3
• VQNGQFCOGVEGHI-UHFFFAOYSA-N 4-[[5-(2-carbamoyl-5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)-1-ethyl-3-methylpyrazolo[3,4-b]pyridin-4-yl]amino]cyclohexane-1-carboxylic acid Chemical compound N=1OC2(CC(C2)C(N)=O)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CCC(C(O)=O)CC1 VQNGQFCOGVEGHI-UHFFFAOYSA-N 0.000 claims description 3
• YTCHCTWWODHXOJ-UHFFFAOYSA-N 4-[[5-(2-carbamoyl-5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)-1-ethylpyrazolo[3,4-b]pyridin-4-yl]amino]cyclohexane-1-carboxylic acid Chemical compound N=1OC2(CC(C2)C(N)=O)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCC(C(O)=O)CC1 YTCHCTWWODHXOJ-UHFFFAOYSA-N 0.000 claims description 3
• OJRQLMUUVTVELN-UHFFFAOYSA-N 4-[[5-(2-cyano-5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)-1-ethyl-3-methylpyrazolo[3,4-b]pyridin-4-yl]amino]cyclohexane-1-carboxylic acid Chemical compound N=1OC2(CC(C2)C#N)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CCC(C(O)=O)CC1 OJRQLMUUVTVELN-UHFFFAOYSA-N 0.000 claims description 3
• XVYRGABPKZHYST-UHFFFAOYSA-N 4-[[5-(2-cyano-5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)-1-ethylpyrazolo[3,4-b]pyridin-4-yl]amino]cyclohexane-1-carboxylic acid Chemical compound N=1OC2(CC(C2)C#N)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCC(C(O)=O)CC1 XVYRGABPKZHYST-UHFFFAOYSA-N 0.000 claims description 3
• GTHSHAZXVCHSHJ-UHFFFAOYSA-N 4-[[5-(8-acetamido-1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)-1-ethyl-3-methylpyrazolo[3,4-b]pyridin-4-yl]amino]cyclohexane-1-carboxylic acid Chemical compound N=1OC2(CCC(CC2)NC(C)=O)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CCC(C(O)=O)CC1 GTHSHAZXVCHSHJ-UHFFFAOYSA-N 0.000 claims description 3
• BBCQRUAZUVLJMR-UHFFFAOYSA-N 4-[[5-(8-amino-1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)-1-ethyl-3-methylpyrazolo[3,4-b]pyridin-4-yl]amino]cyclohexane-1-carboxylic acid Chemical compound N=1OC2(CCC(N)CC2)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CCC(C(O)=O)CC1 BBCQRUAZUVLJMR-UHFFFAOYSA-N 0.000 claims description 3
• WFASOWPGQHGRDY-UHFFFAOYSA-N 4-[[5-(8-amino-1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)-1-ethylpyrazolo[3,4-b]pyridin-4-yl]amino]cyclohexane-1-carboxylic acid Chemical compound N=1OC2(CCC(N)CC2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCC(C(O)=O)CC1 WFASOWPGQHGRDY-UHFFFAOYSA-N 0.000 claims description 3
• CIILTBAAFOELMI-UHFFFAOYSA-N 4-[[5-(8-carbamoyl-1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)-1-ethyl-3-methylpyrazolo[3,4-b]pyridin-4-yl]amino]cyclohexane-1-carboxylic acid Chemical compound N=1OC2(CCC(CC2)C(N)=O)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CCC(C(O)=O)CC1 CIILTBAAFOELMI-UHFFFAOYSA-N 0.000 claims description 3
• SMOSWOHLBJVHHB-UHFFFAOYSA-N 4-[[5-(8-ethoxy-1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)-1-ethylpyrazolo[3,4-b]pyridin-4-yl]amino]cyclohexane-1-carboxylic acid Chemical compound C1CC(OCC)CCC11ON=C(C=2C(=C3C=NN(CC)C3=NC=2)NC2CCC(CC2)C(O)=O)C1 SMOSWOHLBJVHHB-UHFFFAOYSA-N 0.000 claims description 3
• RIUHDDWKKIFDDQ-UHFFFAOYSA-N 5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)-n-(oxan-4-yl)-1-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCCC2)CC=1C1=CN=C2N(C(C)C)N=CC2=C1NC1CCOCC1 RIUHDDWKKIFDDQ-UHFFFAOYSA-N 0.000 claims description 3
• BZJXFAPKHFPWOL-UHFFFAOYSA-N 5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)-n-(oxan-4-yl)-1-propylpyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCCC2)CC=1C1=CN=C2N(CCC)N=CC2=C1NC1CCOCC1 BZJXFAPKHFPWOL-UHFFFAOYSA-N 0.000 claims description 3
• YXXGQMRJSOKODH-UHFFFAOYSA-N 5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)-n-(oxan-4-yl)-1-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCCCC2)CC=1C1=CN=C2N(C(C)C)N=CC2=C1NC1CCOCC1 YXXGQMRJSOKODH-UHFFFAOYSA-N 0.000 claims description 3
• OACURABESMMQKA-UHFFFAOYSA-N 5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)-n-(oxan-4-yl)-1h-pyrazolo[3,4-b]pyridin-4-amine Chemical compound C1C(C=2C(=C3C=NNC3=NC=2)NC2CCOCC2)=NOC11CCCCC1 OACURABESMMQKA-UHFFFAOYSA-N 0.000 claims description 3
• QLVSSTBIEQAWED-UHFFFAOYSA-N 5-(2-ethoxy-5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)-1-ethyl-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound C1C(OCC)CC21ON=C(C=1C(=C3C=NN(CC)C3=NC=1)NC1CCOCC1)C2 QLVSSTBIEQAWED-UHFFFAOYSA-N 0.000 claims description 3
• IQXZEVXJPIPQBA-UHFFFAOYSA-N 5-(5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)-n-(oxan-4-yl)-1-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCC2)CC=1C1=CN=C2N(C(C)C)N=CC2=C1NC1CCOCC1 IQXZEVXJPIPQBA-UHFFFAOYSA-N 0.000 claims description 3
• IFDXQBMAEOUVHI-UHFFFAOYSA-N 5-(5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)-n-(oxan-4-yl)-1-propylpyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCC2)CC=1C1=CN=C2N(CCC)N=CC2=C1NC1CCOCC1 IFDXQBMAEOUVHI-UHFFFAOYSA-N 0.000 claims description 3
• GHOBQQMKHXQKJL-UHFFFAOYSA-N 5-(5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)-n-(oxan-4-yl)-1h-pyrazolo[3,4-b]pyridin-4-amine Chemical compound C1CCC21ON=C(C=1C(=C3C=NNC3=NC=1)NC1CCOCC1)C2 GHOBQQMKHXQKJL-UHFFFAOYSA-N 0.000 claims description 3
• CUOABBOYZKRIDB-UHFFFAOYSA-N 5-[2-(aminomethyl)-5-oxa-6-azaspiro[3.4]oct-6-en-7-yl]-1-ethyl-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CC(CN)C2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 CUOABBOYZKRIDB-UHFFFAOYSA-N 0.000 claims description 3
• QBLFCFZYHKWAEJ-UHFFFAOYSA-N 5-[2-(ethoxymethyl)-5-oxa-6-azaspiro[3.4]oct-6-en-7-yl]-1-ethyl-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound C1C(COCC)CC21ON=C(C=1C(=C3C=NN(CC)C3=NC=1)NC1CCOCC1)C2 QBLFCFZYHKWAEJ-UHFFFAOYSA-N 0.000 claims description 3
• ZUOUNEZWPTYOQF-UHFFFAOYSA-N 7-[1-ethyl-3-methyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-5-oxa-6-azaspiro[3.4]oct-6-en-2-ol Chemical compound N=1OC2(CC(O)C2)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CCOCC1 ZUOUNEZWPTYOQF-UHFFFAOYSA-N 0.000 claims description 3
• RTBBPFYYKHXNEY-UHFFFAOYSA-N 7-[1-ethyl-3-methyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-5-oxa-6-azaspiro[3.4]oct-6-ene-2-carbonitrile Chemical compound N=1OC2(CC(C2)C#N)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CCOCC1 RTBBPFYYKHXNEY-UHFFFAOYSA-N 0.000 claims description 3
• SAUOHRROLLLSHW-UHFFFAOYSA-N 7-[1-ethyl-3-methyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-5-oxa-6-azaspiro[3.4]oct-6-ene-2-carboxamide Chemical compound N=1OC2(CC(C2)C(N)=O)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CCOCC1 SAUOHRROLLLSHW-UHFFFAOYSA-N 0.000 claims description 3
• OZUJBUPJMYOSMD-UHFFFAOYSA-N 7-[1-ethyl-3-methyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-5-oxa-6-azaspiro[3.4]oct-6-ene-2-carboxylic acid Chemical compound N=1OC2(CC(C2)C(O)=O)CC=1C1=CN=C2N(CC)N=C(C)C2=C1NC1CCOCC1 OZUJBUPJMYOSMD-UHFFFAOYSA-N 0.000 claims description 3
• HPMRQIJYOPRJQX-UHFFFAOYSA-N 7-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-5-oxa-6-azaspiro[3.4]oct-6-en-2-amine Chemical compound N=1OC2(CC(N)C2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 HPMRQIJYOPRJQX-UHFFFAOYSA-N 0.000 claims description 3
• DYTFKEFWANZBQA-UHFFFAOYSA-N 7-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-5-oxa-6-azaspiro[3.4]oct-6-ene-2-carbonitrile Chemical compound N=1OC2(CC(C2)C#N)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 DYTFKEFWANZBQA-UHFFFAOYSA-N 0.000 claims description 3
• AATZSBIXYVDCLC-UHFFFAOYSA-N 7-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-5-oxa-6-azaspiro[3.4]oct-6-ene-2-carboxamide Chemical compound N=1OC2(CC(C2)C(N)=O)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 AATZSBIXYVDCLC-UHFFFAOYSA-N 0.000 claims description 3
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