JP2010521451A5 - - Google Patents
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- JP2010521451A5 JP2010521451A5 JP2009553263A JP2009553263A JP2010521451A5 JP 2010521451 A5 JP2010521451 A5 JP 2010521451A5 JP 2009553263 A JP2009553263 A JP 2009553263A JP 2009553263 A JP2009553263 A JP 2009553263A JP 2010521451 A5 JP2010521451 A5 JP 2010521451A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- pyrazolo
- oxa
- azaspiro
- ethyl
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 515
- -1 1-oxa-2-azaspiro [4.4] non-2-en-3-yl Chemical group 0.000 claims 89
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 43
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 35
- 125000000217 alkyl group Chemical group 0.000 claims 24
- NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Natural products OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 20
- 238000000034 method Methods 0.000 claims 17
- 238000004519 manufacturing process Methods 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 125000005843 halogen group Chemical group 0.000 claims 13
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 12
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims 12
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims 11
- 229960004979 fampridine Drugs 0.000 claims 11
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims 10
- 230000003301 hydrolyzing effect Effects 0.000 claims 8
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000006239 protecting group Chemical group 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 3
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims 3
- 230000001590 oxidative effect Effects 0.000 claims 3
- 229910052698 phosphorus Inorganic materials 0.000 claims 3
- 239000011574 phosphorus Substances 0.000 claims 3
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- JFNPQHWGYOMASF-UHFFFAOYSA-N 2-methyloct-6-enamide Chemical compound CC(CCCC=CC)C(=O)N JFNPQHWGYOMASF-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 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 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- WREXZTSEBLTXAX-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]-n-(oxan-4-yl)-5-(4,9,12-trioxa-3-azadispiro[4.2.4^{8}.2^{5}]tetradec-2-en-2-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound C1=CC(OC)=CC=C1CN1C2=NC=C(C=3CC4(ON=3)CCC3(CC4)OCCO3)C(NC3CCOCC3)=C2C=N1 WREXZTSEBLTXAX-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- LFUHYQRYXVUOLV-UHFFFAOYSA-N 1-ethyl-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)-n-pyridin-3-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCCC2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1=CC=CN=C1 LFUHYQRYXVUOLV-UHFFFAOYSA-N 0.000 claims 1
- NNJDRYKVEUFUHG-UHFFFAOYSA-N 1-ethyl-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)-n-pyridin-4-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCCC2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1=CC=NC=C1 NNJDRYKVEUFUHG-UHFFFAOYSA-N 0.000 claims 1
- IZTRKCIWIGVZKE-UHFFFAOYSA-N 1-ethyl-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)-n-pyrimidin-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCCC2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1=NC=CC=N1 IZTRKCIWIGVZKE-UHFFFAOYSA-N 0.000 claims 1
- CWTRIHWOUYCONO-UHFFFAOYSA-N 1-ethyl-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)-n-pyrimidin-5-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCCC2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1=CN=CN=C1 CWTRIHWOUYCONO-UHFFFAOYSA-N 0.000 claims 1
- OKOGEYGAUZXTFL-UHFFFAOYSA-N 1-ethyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)-n-(1,2,4-triazin-3-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCCCC2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1=NC=CN=N1 OKOGEYGAUZXTFL-UHFFFAOYSA-N 0.000 claims 1
- KKSJLCWBELXIPP-UHFFFAOYSA-N 1-ethyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)-n-(1,2,4-triazin-5-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCCCC2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1=CN=NC=N1 KKSJLCWBELXIPP-UHFFFAOYSA-N 0.000 claims 1
- PGJALNZVFZCADV-UHFFFAOYSA-N 1-ethyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)-n-(1,2,4-triazol-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCCCC2)CC=1C1=CN=C2N(CC)N=CC2=C1NN1C=NN=C1 PGJALNZVFZCADV-UHFFFAOYSA-N 0.000 claims 1
- DETSAEAHDBMFRP-UHFFFAOYSA-N 1-ethyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)-n-(1-propan-2-ylpiperidin-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC2(CCCCC2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(C)C)CC1 DETSAEAHDBMFRP-UHFFFAOYSA-N 0.000 claims 1
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- 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 1
- KNJXXFJHUBTDOO-UHFFFAOYSA-N 3-[[1-ethyl-5-(2-hydroxy-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(CC(O)C2)CC=1C1=CN=C2N(CC)N=CC2=C1NC1CC(C(O)=O)C1 KNJXXFJHUBTDOO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
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- 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 1
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| WO2007031838A1 (en) * | 2005-09-16 | 2007-03-22 | Ranbaxy Laboratories Limited | Substituted pyrazolo [3,4-b] pyridines as phosphodiesterase inhibitors |
| US7723330B2 (en) * | 2006-03-07 | 2010-05-25 | Array Biopharma Inc. | Heterobicyclic pyrazole compounds and methods of use |
| US20110053931A1 (en) * | 2006-06-08 | 2011-03-03 | John Gaudino | Quinoline compounds and methods of use |
| DE602007013573D1 (de) * | 2006-08-16 | 2011-05-12 | Hoffmann La Roche | Nicht-nukleosidische reverse-transkriptase-hemmer |
| EP2346867A1 (en) * | 2008-09-19 | 2011-07-27 | Ranbaxy Laboratories Limited | Phosphodiestarase inhibitors |
| DK2509609T3 (da) | 2009-12-08 | 2014-11-10 | Univ Vanderbilt | Forbedrede fremgangsmåder og sammensætninger for venehøst og autotransplantation |
| US10034861B2 (en) * | 2016-07-04 | 2018-07-31 | H. Lundbeck A/S | 1H-pyrazolo[4,3-b]pyridines as PDE1 inhibitors |
| WO2018049271A1 (en) * | 2016-09-09 | 2018-03-15 | Flx Bio, Inc. | Chemokine receptor modulators and uses thereof |
| JOP20190126A1 (ar) | 2016-12-22 | 2019-05-28 | H Lundbeck As | بيرازولو [3، 4-b] بيريدينات وإيميدازو [1، 5-b] بيريدازينات على هيئة مثبطات PDE1 |
| EA037544B1 (ru) * | 2017-04-04 | 2021-04-12 | Х. Лундбекк А/С | ПРИМЕНЕНИЕ 1H-ПИРАЗОЛО[4,3-b]ПИРИДИНОВ В КАЧЕСТВЕ ИНГИБИТОРОВ PDE1 |
| RU2020118913A (ru) * | 2017-12-14 | 2022-01-14 | Х. Лундбекк А/С (H. Lundbeck A/S) | Виды комбинированного лечения, предусматривающего введение 1h-пиразолo[4,3-b]пиридинов |
| AR113926A1 (es) | 2017-12-14 | 2020-07-01 | H Lundbeck As | Derivados de 1h-pirazolo[4,3-b]piridinas |
| US10766893B2 (en) | 2017-12-20 | 2020-09-08 | H. Lundbeck A/S | 1H-pyrazolo[4,3-b]pyridines as PDE1 inhibitors |
| TW201927784A (zh) * | 2017-12-20 | 2019-07-16 | 丹麥商Ｈ 朗德貝克公司 | 作為pde1抑制劑之大環 |
| US11535611B2 (en) | 2017-12-20 | 2022-12-27 | H. Lundbeck A/S | Pyrazolo[3,4-B]pyridines and imidazo[1,5-B]pyridazines as PDE1 inhibitors |
| CN113200997B (zh) * | 2021-05-07 | 2023-10-03 | 上海合全医药有限公司 | 2,5-二氧杂-8-氮杂螺[3.5]壬烷及其盐的合成方法 |
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-
2008
- 2008-03-14 SI SI200830590T patent/SI2124944T1/sl unknown
- 2008-03-14 EP EP08737621A patent/EP2124944B1/en not_active Not-in-force
- 2008-03-14 ES ES08737621T patent/ES2382715T3/es active Active
- 2008-03-14 JP JP2009553263A patent/JP5671236B2/ja not_active Expired - Fee Related
- 2008-03-14 PL PL08737621T patent/PL2124944T3/pl unknown
- 2008-03-14 MX MX2009009793A patent/MX2009009793A/es active IP Right Grant
- 2008-03-14 EA EA200970852A patent/EA018670B9/ru not_active IP Right Cessation
- 2008-03-14 AT AT08737621T patent/ATE545417T1/de active
- 2008-03-14 NZ NZ579645A patent/NZ579645A/en not_active IP Right Cessation
- 2008-03-14 KR KR1020097021120A patent/KR101568884B1/ko not_active Expired - Fee Related
- 2008-03-14 US US12/531,043 patent/US8420666B2/en not_active Expired - Fee Related
- 2008-03-14 PT PT08737621T patent/PT2124944E/pt unknown
- 2008-03-14 HR HRP20120361AT patent/HRP20120361T1/hr unknown
- 2008-03-14 AP AP2009004977A patent/AP2453A/xx active
- 2008-03-14 CN CN201310379773.0A patent/CN103497185A/zh active Pending
- 2008-03-14 CN CN200880014410A patent/CN101801376A/zh active Pending
- 2008-03-14 AU AU2008224541A patent/AU2008224541B2/en not_active Ceased
- 2008-03-14 DK DK08737621.6T patent/DK2124944T3/da active
- 2008-03-14 WO PCT/IB2008/050943 patent/WO2008111010A1/en not_active Ceased
- 2008-03-14 CA CA2680625A patent/CA2680625C/en not_active Expired - Fee Related
-
2009
- 2009-09-15 ZA ZA200906418A patent/ZA200906418B/xx unknown
-
2012
- 2012-04-26 CY CY20121100403T patent/CY1112805T1/el unknown
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