JP2012509332A5 - - Google Patents
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- JP2012509332A5 JP2012509332A5 JP2011537547A JP2011537547A JP2012509332A5 JP 2012509332 A5 JP2012509332 A5 JP 2012509332A5 JP 2011537547 A JP2011537547 A JP 2011537547A JP 2011537547 A JP2011537547 A JP 2011537547A JP 2012509332 A5 JP2012509332 A5 JP 2012509332A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- pyrrolo
- quinolin
- pyrimidin
- amine
- 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 description 98
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- -1 sulfo, sulfonate ester Chemical class 0.000 claims description 37
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 29
- 125000001475 halogen functional group Chemical group 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 208000002193 Pain Diseases 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 9
- 208000023504 respiratory system disease Diseases 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000012453 solvate Substances 0.000 claims description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- 208000020925 Bipolar disease Diseases 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 208000037765 diseases and disorders Diseases 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 230000001404 mediated effect Effects 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 230000000155 isotopic effect Effects 0.000 claims description 7
- NMPMKPIPOOEJHL-UHFFFAOYSA-N n-[6-(cyclohexylmethyl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1C2=NC=NC(NC=3C=C4C=CC=CC4=NC=3)=C2CN1CC1CCCCC1 NMPMKPIPOOEJHL-UHFFFAOYSA-N 0.000 claims description 7
- VPAOHQFKKUUFMF-UHFFFAOYSA-N n-[6-(cyclopentylmethyl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1C2=NC=NC(NC=3C=C4C=CC=CC4=NC=3)=C2CN1CC1CCCC1 VPAOHQFKKUUFMF-UHFFFAOYSA-N 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 239000000651 prodrug Substances 0.000 claims description 7
- 229940002612 prodrug Drugs 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 208000023275 Autoimmune disease Diseases 0.000 claims description 6
- 208000018737 Parkinson disease Diseases 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 206010015037 epilepsy Diseases 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- OXHWXFLJSBMMDH-UHFFFAOYSA-N methyl 5-[[4-(quinolin-3-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidin-6-yl]sulfonyl]furan-2-carboxylate Chemical compound O1C(C(=O)OC)=CC=C1S(=O)(=O)N1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 OXHWXFLJSBMMDH-UHFFFAOYSA-N 0.000 claims description 6
- URLCMVOXBIWZSE-UHFFFAOYSA-N n-(6-benzyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl)quinolin-3-amine Chemical compound C1C2=NC=NC(NC=3C=C4C=CC=CC4=NC=3)=C2CN1CC1=CC=CC=C1 URLCMVOXBIWZSE-UHFFFAOYSA-N 0.000 claims description 6
- UEJPDSPEIFFZQJ-UHFFFAOYSA-N n-[6-(1,3-benzodioxol-4-ylmethyl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1C2=NC=NC(NC=3C=C4C=CC=CC4=NC=3)=C2CN1CC1=CC=CC2=C1OCO2 UEJPDSPEIFFZQJ-UHFFFAOYSA-N 0.000 claims description 6
- MATKADOETFQELG-UHFFFAOYSA-N n-[6-(1-cyclohexylethyl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1C2=NC=NC(NC=3C=C4C=CC=CC4=NC=3)=C2CN1C(C)C1CCCCC1 MATKADOETFQELG-UHFFFAOYSA-N 0.000 claims description 6
- CMXGMWHUWHCCOI-UHFFFAOYSA-N n-[6-(2,3-dihydro-1-benzofuran-7-ylmethyl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1C2=NC=NC(NC=3C=C4C=CC=CC4=NC=3)=C2CN1CC1=CC=CC2=C1OCC2 CMXGMWHUWHCCOI-UHFFFAOYSA-N 0.000 claims description 6
- GDOTUCVLCYDLRT-UHFFFAOYSA-N n-[6-(2-ethylbutyl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1=CC=CC2=CC(NC=3N=CN=C4CN(CC4=3)CC(CC)CC)=CN=C21 GDOTUCVLCYDLRT-UHFFFAOYSA-N 0.000 claims description 6
- OKJYGWDMPXAUFC-UHFFFAOYSA-N n-[6-(2-methylphenyl)sulfonyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound CC1=CC=CC=C1S(=O)(=O)N1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 OKJYGWDMPXAUFC-UHFFFAOYSA-N 0.000 claims description 6
- IQORHRFPUBHURL-UHFFFAOYSA-N n-[6-(2-phenylethyl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1C2=NC=NC(NC=3C=C4C=CC=CC4=NC=3)=C2CN1CCC1=CC=CC=C1 IQORHRFPUBHURL-UHFFFAOYSA-N 0.000 claims description 6
- VZXCBUPBKYCWKB-UHFFFAOYSA-N n-[6-(2-phenylpropyl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1C2=NC=NC(NC=3C=C4C=CC=CC4=NC=3)=C2CN1CC(C)C1=CC=CC=C1 VZXCBUPBKYCWKB-UHFFFAOYSA-N 0.000 claims description 6
- RGZDSVSGHDVWSN-UHFFFAOYSA-N n-[6-(oxan-4-ylmethyl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1C2=NC=NC(NC=3C=C4C=CC=CC4=NC=3)=C2CN1CC1CCOCC1 RGZDSVSGHDVWSN-UHFFFAOYSA-N 0.000 claims description 6
- NGQJKDAKDWGKAR-UHFFFAOYSA-N n-[6-(pyridin-4-ylmethyl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1C2=NC=NC(NC=3C=C4C=CC=CC4=NC=3)=C2CN1CC1=CC=NC=C1 NGQJKDAKDWGKAR-UHFFFAOYSA-N 0.000 claims description 6
- BXJPVBCVFWTXJF-UHFFFAOYSA-N n-[6-(thian-4-ylmethyl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1C2=NC=NC(NC=3C=C4C=CC=CC4=NC=3)=C2CN1CC1CCSCC1 BXJPVBCVFWTXJF-UHFFFAOYSA-N 0.000 claims description 6
- DMBHWVWCCASGGF-UHFFFAOYSA-N n-[6-[(2,3-dimethylphenyl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound CC1=CC=CC(CN2CC3=C(NC=4C=C5C=CC=CC5=NC=4)N=CN=C3C2)=C1C DMBHWVWCCASGGF-UHFFFAOYSA-N 0.000 claims description 6
- QTHXXCNBQIQMPH-UHFFFAOYSA-N n-[6-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound S1C(C)=NC(C)=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 QTHXXCNBQIQMPH-UHFFFAOYSA-N 0.000 claims description 6
- WELWHSBMCYLXFM-UHFFFAOYSA-N n-[6-[(2,5-dimethylphenyl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound CC1=CC=C(C)C(CN2CC3=C(NC=4C=C5C=CC=CC5=NC=4)N=CN=C3C2)=C1 WELWHSBMCYLXFM-UHFFFAOYSA-N 0.000 claims description 6
- MAJXXFOPDXBGFL-UHFFFAOYSA-N n-[6-[(2-chlorophenyl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound ClC1=CC=CC=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 MAJXXFOPDXBGFL-UHFFFAOYSA-N 0.000 claims description 6
- RWKRDZSYHQTBCD-UHFFFAOYSA-N n-[6-[(2-ethoxyphenyl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound CCOC1=CC=CC=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 RWKRDZSYHQTBCD-UHFFFAOYSA-N 0.000 claims description 6
- VQPCFLJHJHFYIK-UHFFFAOYSA-N n-[6-[(2-ethyl-4-methyl-1,3-thiazol-5-yl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound S1C(CC)=NC(C)=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 VQPCFLJHJHFYIK-UHFFFAOYSA-N 0.000 claims description 6
- KZMLNIBVCWOQKC-UHFFFAOYSA-N n-[6-[(2-ethylphenyl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound CCC1=CC=CC=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 KZMLNIBVCWOQKC-UHFFFAOYSA-N 0.000 claims description 6
- WKPPAJLOBSSZMO-UHFFFAOYSA-N n-[6-[(2-fluorophenyl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound FC1=CC=CC=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 WKPPAJLOBSSZMO-UHFFFAOYSA-N 0.000 claims description 6
- MMJNAXYWDNGLHG-UHFFFAOYSA-N n-[6-[(2-methoxyphenyl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound COC1=CC=CC=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 MMJNAXYWDNGLHG-UHFFFAOYSA-N 0.000 claims description 6
- GJMHDILRWAOXOP-UHFFFAOYSA-N n-[6-[(2-methylphenyl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound CC1=CC=CC=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 GJMHDILRWAOXOP-UHFFFAOYSA-N 0.000 claims description 6
- QHEHZWJTPUYWPO-UHFFFAOYSA-N n-[6-[(2-methylpyridin-3-yl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound CC1=NC=CC=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 QHEHZWJTPUYWPO-UHFFFAOYSA-N 0.000 claims description 6
- AIXRTPJXNXUODG-UHFFFAOYSA-N n-[6-[(2-methylsulfanylphenyl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound CSC1=CC=CC=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 AIXRTPJXNXUODG-UHFFFAOYSA-N 0.000 claims description 6
- AOHLUGDMUDZXLC-UHFFFAOYSA-N n-[6-[(3-methylfuran-2-yl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1=COC(CN2CC3=C(NC=4C=C5C=CC=CC5=NC=4)N=CN=C3C2)=C1C AOHLUGDMUDZXLC-UHFFFAOYSA-N 0.000 claims description 6
- LOZKIHJPBQFNCA-UHFFFAOYSA-N n-[6-[(3-methylpyridin-4-yl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound CC1=CN=CC=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 LOZKIHJPBQFNCA-UHFFFAOYSA-N 0.000 claims description 6
- YHHXDPDCIUYATI-UHFFFAOYSA-N n-[6-[(4-methyl-1,3-thiazol-5-yl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound N1=CSC(CN2CC3=C(NC=4C=C5C=CC=CC5=NC=4)N=CN=C3C2)=C1C YHHXDPDCIUYATI-UHFFFAOYSA-N 0.000 claims description 6
- DHAOQKJDAGLULX-UHFFFAOYSA-N n-[6-[[2-(trifluoromethoxy)phenyl]methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound FC(F)(F)OC1=CC=CC=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 DHAOQKJDAGLULX-UHFFFAOYSA-N 0.000 claims description 6
- NTVBZYKBURUSPE-UHFFFAOYSA-N n-[6-[[2-(trifluoromethyl)phenyl]methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound FC(F)(F)C1=CC=CC=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 NTVBZYKBURUSPE-UHFFFAOYSA-N 0.000 claims description 6
- TWPDIGQSOSWRLR-UHFFFAOYSA-N n-[6-[[3-(trifluoromethoxy)phenyl]methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound FC(F)(F)OC1=CC=CC(CN2CC3=C(NC=4C=C5C=CC=CC5=NC=4)N=CN=C3C2)=C1 TWPDIGQSOSWRLR-UHFFFAOYSA-N 0.000 claims description 6
- 230000000926 neurological effect Effects 0.000 claims description 6
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 6
- 125000004001 thioalkyl group Chemical group 0.000 claims description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
- YLKIPCIXTBPALX-UHFFFAOYSA-N n-[6-[[3-(trifluoromethyl)phenyl]methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound FC(F)(F)C1=CC=CC(CN2CC3=C(NC=4C=C5C=CC=CC5=NC=4)N=CN=C3C2)=C1 YLKIPCIXTBPALX-UHFFFAOYSA-N 0.000 claims description 5
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- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
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- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
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- CETZFAWYTOVKPB-UHFFFAOYSA-N n-[6-[(2,3-difluorophenyl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound FC1=CC=CC(CN2CC3=C(NC=4C=C5C=CC=CC5=NC=4)N=CN=C3C2)=C1F CETZFAWYTOVKPB-UHFFFAOYSA-N 0.000 claims description 4
- STJXKAVMFCGHSK-UHFFFAOYSA-N n-[6-[(2-cyclopropylphenyl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1C2=NC=NC(NC=3C=C4C=CC=CC4=NC=3)=C2CN1CC1=CC=CC=C1C1CC1 STJXKAVMFCGHSK-UHFFFAOYSA-N 0.000 claims description 4
- MMJMOQZQCNABKD-UHFFFAOYSA-N n-[6-[(3-methylphenyl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound CC1=CC=CC(CN2CC3=C(NC=4C=C5C=CC=CC5=NC=4)N=CN=C3C2)=C1 MMJMOQZQCNABKD-UHFFFAOYSA-N 0.000 claims description 4
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- JVZSYPHUAVFKEG-UHFFFAOYSA-N n-[6-[(1,5-dimethylpyrazol-4-yl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1=NN(C)C(C)=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 JVZSYPHUAVFKEG-UHFFFAOYSA-N 0.000 claims description 2
- AMJHWWUFRPQZEX-UHFFFAOYSA-N n-[6-[(1-methylpiperidin-4-yl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1CN(C)CCC1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 AMJHWWUFRPQZEX-UHFFFAOYSA-N 0.000 claims description 2
- FJYFJDZWVBGKHN-UHFFFAOYSA-N n-[6-[(2,4-dimethyl-1,3-thiazol-5-yl)sulfonyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound S1C(C)=NC(C)=C1S(=O)(=O)N1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 FJYFJDZWVBGKHN-UHFFFAOYSA-N 0.000 claims description 2
- ZLJJTNOEGVFXLO-UHFFFAOYSA-N n-[6-[(2,4-dimethylphenyl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound CC1=CC(C)=CC=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 ZLJJTNOEGVFXLO-UHFFFAOYSA-N 0.000 claims description 2
- WIOYCYMSGLPTIG-UHFFFAOYSA-N n-[6-[(2,6-dimethylphenyl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound CC1=CC=CC(C)=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 WIOYCYMSGLPTIG-UHFFFAOYSA-N 0.000 claims description 2
- NLEQZIRXVSIEQL-UHFFFAOYSA-N n-[6-[(2-chloro-1,3-thiazol-5-yl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound S1C(Cl)=NC=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 NLEQZIRXVSIEQL-UHFFFAOYSA-N 0.000 claims description 2
- KONPHTMKWWMXIE-UHFFFAOYSA-N n-[6-[(2-methyl-1,3-thiazol-4-yl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound S1C(C)=NC(CN2CC3=C(NC=4C=C5C=CC=CC5=NC=4)N=CN=C3C2)=C1 KONPHTMKWWMXIE-UHFFFAOYSA-N 0.000 claims description 2
- BEMGVSBLAMGLJJ-UHFFFAOYSA-N n-[6-[(2-methyl-1,3-thiazol-5-yl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound S1C(C)=NC=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 BEMGVSBLAMGLJJ-UHFFFAOYSA-N 0.000 claims description 2
- VBCOYQQVNQZDFL-UHFFFAOYSA-N n-[6-[(2-methylfuran-3-yl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound O1C=CC(CN2CC3=C(NC=4C=C5C=CC=CC5=NC=4)N=CN=C3C2)=C1C VBCOYQQVNQZDFL-UHFFFAOYSA-N 0.000 claims description 2
- SAMPCPJNRMNVDN-UHFFFAOYSA-N n-[6-[(2-methylpyrazol-3-yl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound CN1N=CC=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 SAMPCPJNRMNVDN-UHFFFAOYSA-N 0.000 claims description 2
- JLVGQTYJFXPELZ-UHFFFAOYSA-N n-[6-[(2-propan-2-yloxyphenyl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound CC(C)OC1=CC=CC=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 JLVGQTYJFXPELZ-UHFFFAOYSA-N 0.000 claims description 2
- XSNPCMGGUJXIES-UHFFFAOYSA-N n-[6-[(2-propoxyphenyl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound CCCOC1=CC=CC=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 XSNPCMGGUJXIES-UHFFFAOYSA-N 0.000 claims description 2
- PMXRHPRGDVTDQY-UHFFFAOYSA-N n-[6-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound CC1=NOC(C)=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 PMXRHPRGDVTDQY-UHFFFAOYSA-N 0.000 claims description 2
- DJNNELPNCGBWNU-UHFFFAOYSA-N n-[6-[(3-methyloxetan-3-yl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1C2=NC=NC(NC=3C=C4C=CC=CC4=NC=3)=C2CN1CC1(C)COC1 DJNNELPNCGBWNU-UHFFFAOYSA-N 0.000 claims description 2
- GWOFPFUEIXYQHH-UHFFFAOYSA-N n-[6-[(3-methylpyridin-2-yl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound CC1=CC=CN=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 GWOFPFUEIXYQHH-UHFFFAOYSA-N 0.000 claims description 2
- SIHXRDFFGNSHLP-UHFFFAOYSA-N n-[6-[(4-methyl-1,3-thiazol-2-yl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound CC1=CSC(CN2CC3=C(NC=4C=C5C=CC=CC5=NC=4)N=CN=C3C2)=N1 SIHXRDFFGNSHLP-UHFFFAOYSA-N 0.000 claims description 2
- BZKOBOOGPBXJTE-UHFFFAOYSA-N n-[6-[5-(1,3-oxazol-5-yl)thiophen-2-yl]sulfonyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1C2=NC=NC(NC=3C=C4C=CC=CC4=NC=3)=C2CN1S(=O)(=O)C(S1)=CC=C1C1=CN=CO1 BZKOBOOGPBXJTE-UHFFFAOYSA-N 0.000 claims description 2
- AEVNMMWAYRKSJV-UHFFFAOYSA-N n-[6-[[2-methyl-6-(trifluoromethyl)pyridin-3-yl]methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical class CC1=NC(C(F)(F)F)=CC=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 AEVNMMWAYRKSJV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- NKXAYZVDQUSFES-UHFFFAOYSA-N n-cyclohexyl-4-(quinolin-3-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxamide Chemical compound C1C2=NC=NC(NC=3C=C4C=CC=CC4=NC=3)=C2CN1C(=O)NC1CCCCC1 NKXAYZVDQUSFES-UHFFFAOYSA-N 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical class C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- AXIUFDZXPKAKMV-UHFFFAOYSA-N tert-butyl 4-(quinolin-3-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate Chemical compound C1=CC=CC2=CC(NC=3N=CN=C4CN(CC4=3)C(=O)OC(C)(C)C)=CN=C21 AXIUFDZXPKAKMV-UHFFFAOYSA-N 0.000 claims description 2
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- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims 1
- 208000001647 Renal Insufficiency Diseases 0.000 claims 1
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11629208P | 2008-11-19 | 2008-11-19 | |
| US61/116,292 | 2008-11-19 | ||
| US13960008P | 2008-12-20 | 2008-12-20 | |
| US61/139,600 | 2008-12-20 | ||
| PCT/US2009/064757 WO2010059610A1 (en) | 2008-11-19 | 2009-11-17 | 6, 7 -dihydro- 5h- pyrrolo [3, 4-d] pyrimidin-4-yl] -quinolin-3 -ylamine compounds useful as faah modulators and uses thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012509332A JP2012509332A (ja) | 2012-04-19 |
| JP2012509332A5 true JP2012509332A5 (https=) | 2012-11-22 |
| JP5539376B2 JP5539376B2 (ja) | 2014-07-02 |
Family
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| JP2011537547A Expired - Fee Related JP5539376B2 (ja) | 2008-11-19 | 2009-11-17 | Ｆａａｈ調整因子として有用な６，７−ジヒドロ−５ｈ−ピロロ［３，４−ｄ］ピリミジン−４−イル］キノリン−３−イルアミン化合物およびその使用 |
Country Status (5)
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| US (1) | US20110257208A1 (https=) |
| EP (1) | EP2364316A1 (https=) |
| JP (1) | JP5539376B2 (https=) |
| CA (1) | CA2744343A1 (https=) |
| WO (1) | WO2010059610A1 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011085216A2 (en) | 2010-01-08 | 2011-07-14 | Ironwood Pharmaceuticals, Inc. | Use of faah inhibitors for treating parkinson's disease and restless legs syndrome |
| WO2011123719A2 (en) | 2010-03-31 | 2011-10-06 | Ironwood Pharmaceuticals, Inc. | Use of faah inhibitors for treating abdominal, visceral and pelvic pain |
| HRP20201384T1 (hr) | 2014-01-01 | 2020-11-27 | Medivation Technologies Llc | Spojevi i postupci njihove upotrebe |
| CN119053595A (zh) | 2022-03-28 | 2024-11-29 | 尼坎治疗公司 | 作为细胞周期蛋白依赖性激酶2抑制剂的磺酰氨基衍生物 |
| WO2025188951A1 (en) * | 2024-03-06 | 2025-09-12 | Ovid Therapeutics Inc. | Fused amino pyrimidine compounds for treatment of seizure disorders |
| WO2025188974A1 (en) * | 2024-03-06 | 2025-09-12 | Ovid Therapeutics Inc. | Fused amino pyrimidine compounds for treatment of autism spectrum disorder, obsessive compulsive disorder and tics |
| WO2025188976A1 (en) * | 2024-03-06 | 2025-09-12 | Ovid Therapeutics Inc. | Fused amino pyrimidine compounds for treatment of neurodegenerative disorders |
| WO2025188973A1 (en) * | 2024-03-06 | 2025-09-12 | Ovid Therapeutics Inc. | Fused amino pyrimidine compounds for treatment of 22q11.2 deletion/duplication syndromes |
| US20260048062A1 (en) * | 2024-03-06 | 2026-02-19 | Ovid Therapeutics Inc. | Fused amino pyrimidine compounds for treatment of psychosis and psychotic disorders |
| WO2025188953A1 (en) * | 2024-03-06 | 2025-09-12 | Ovid Therapeutics Inc. | Fused amino pyrimidine compounds for treatment of neuropathic and neuro-inflammatory pain |
| WO2025188977A1 (en) * | 2024-03-06 | 2025-09-12 | Ovid Therapeutics Inc. | Fused amino pyrimidine compounds for treatment of addiction and insomnia |
| US20250281500A1 (en) * | 2024-03-06 | 2025-09-11 | Ovid Therapeutics Inc. | Fused amino pyrimidine compounds and pridopidine for treatment of huntington’s disease |
| US20250281498A1 (en) * | 2024-03-06 | 2025-09-11 | Ovid Therapeutics Inc. | Fused amino pyrimidine compounds for treatment of synucleinopathies and tdp-43 proteinopathies |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1230225A2 (en) * | 1999-11-01 | 2002-08-14 | Eli Lilly And Company | Pharmaceutically active 4-substituted pyrimidine derivatives |
| EP1317450B1 (en) * | 2000-09-15 | 2006-11-22 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| WO2008021456A2 (en) * | 2006-08-16 | 2008-02-21 | Cytovia, Inc. | N-aryl-5,7-dihydrofuro[3,4-d]pyrimidin-4-amines and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| CA2676715A1 (en) * | 2007-02-12 | 2008-08-21 | Merck & Co., Inc. | Piperazine derivatives for treatment of ad and related conditions |
| WO2009011904A1 (en) * | 2007-07-19 | 2009-01-22 | Renovis, Inc. | Compounds useful as faah modulators and uses thereof |
| CN102227422A (zh) * | 2008-09-30 | 2011-10-26 | 阿斯利康(瑞典)有限公司 | 杂环jak激酶抑制剂 |
-
2009
- 2009-11-17 CA CA2744343A patent/CA2744343A1/en not_active Abandoned
- 2009-11-17 WO PCT/US2009/064757 patent/WO2010059610A1/en not_active Ceased
- 2009-11-17 EP EP09793640A patent/EP2364316A1/en not_active Withdrawn
- 2009-11-17 US US13/130,051 patent/US20110257208A1/en not_active Abandoned
- 2009-11-17 JP JP2011537547A patent/JP5539376B2/ja not_active Expired - Fee Related
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