JP2012509332A5 - - Google Patents
Download PDFInfo
- Publication number
- 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
Links
- 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
- 208000004296 neuralgia Diseases 0.000 claims description 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 5
- 208000021722 neuropathic pain Diseases 0.000 claims description 5
- 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
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- 206010063409 Acarodermatitis Diseases 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
- 208000000094 Chronic Pain Diseases 0.000 claims description 4
- 208000006561 Cluster Headache Diseases 0.000 claims description 4
- 208000030814 Eating disease Diseases 0.000 claims description 4
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 4
- 208000010412 Glaucoma Diseases 0.000 claims description 4
- 206010019233 Headaches Diseases 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 206010061218 Inflammation Diseases 0.000 claims description 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
- 206010065390 Inflammatory pain Diseases 0.000 claims description 4
- 208000019695 Migraine disease Diseases 0.000 claims description 4
- 208000008238 Muscle Spasticity Diseases 0.000 claims description 4
- 206010028813 Nausea Diseases 0.000 claims description 4
- 208000012902 Nervous system disease Diseases 0.000 claims description 4
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims description 4
- 208000025966 Neurological disease Diseases 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- 208000003251 Pruritus Diseases 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 4
- 241000447727 Scabies Species 0.000 claims description 4
- 206010043269 Tension headache Diseases 0.000 claims description 4
- 208000008548 Tension-Type Headache Diseases 0.000 claims description 4
- 206010047700 Vomiting Diseases 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- 230000001154 acute effect Effects 0.000 claims description 4
- 208000005298 acute pain Diseases 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 201000009961 allergic asthma Diseases 0.000 claims description 4
- 201000010105 allergic rhinitis Diseases 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 230000036506 anxiety Effects 0.000 claims description 4
- 206010003246 arthritis Diseases 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 150000001540 azides Chemical class 0.000 claims description 4
- 208000028683 bipolar I disease Diseases 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 208000018912 cluster headache syndrome Diseases 0.000 claims description 4
- 208000010877 cognitive disease Diseases 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 235000014632 disordered eating Nutrition 0.000 claims description 4
- 206010014599 encephalitis Diseases 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 231100000869 headache Toxicity 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 230000002757 inflammatory effect Effects 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- 150000002632 lipids Chemical class 0.000 claims description 4
- 206010027599 migraine Diseases 0.000 claims description 4
- 208000010125 myocardial infarction Diseases 0.000 claims description 4
- HDAHKFVWINEYID-UHFFFAOYSA-N n-[6-(1h-indol-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=C1NC=C2 HDAHKFVWINEYID-UHFFFAOYSA-N 0.000 claims description 4
- DFFRZMMWRYVPBV-UHFFFAOYSA-N n-[6-(3-methylbutyl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1=CC=CC2=CC(NC=3N=CN=C4CN(CC4=3)CCC(C)C)=CN=C21 DFFRZMMWRYVPBV-UHFFFAOYSA-N 0.000 claims description 4
- 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
- 230000008693 nausea Effects 0.000 claims description 4
- 230000004770 neurodegeneration Effects 0.000 claims description 4
- 230000003959 neuroinflammation Effects 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 230000000241 respiratory effect Effects 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 208000005687 scabies Diseases 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- 208000019116 sleep disease Diseases 0.000 claims description 4
- 208000018198 spasticity Diseases 0.000 claims description 4
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 4
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- 150000003456 sulfonamides Chemical class 0.000 claims description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 208000004371 toothache Diseases 0.000 claims description 4
- 230000008673 vomiting Effects 0.000 claims description 4
- WPHOUWKOUQMIDP-UHFFFAOYSA-N 2-chloro-4-[(5-methyl-1h-pyrazol-3-yl)amino]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid Chemical compound N1C(C)=CC(NC=2C=3CN(CC=3N=C(Cl)N=2)C(O)=O)=N1 WPHOUWKOUQMIDP-UHFFFAOYSA-N 0.000 claims description 3
- WPNYOUZVWRUBTR-UHFFFAOYSA-N 2-chloro-4-[3-(dimethylamino)-5-methoxyanilino]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid Chemical compound CN(C)C1=CC(OC)=CC(NC=2C=3CN(CC=3N=C(Cl)N=2)C(O)=O)=C1 WPNYOUZVWRUBTR-UHFFFAOYSA-N 0.000 claims description 3
- AQDJBCDVWZZKAJ-UHFFFAOYSA-N 4-(5-tert-butyl-2-methylanilino)-2-[4-(4-methoxyphenyl)piperazin-1-yl]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2N=C(NC=3C(=CC=C(C=3)C(C)(C)C)C)C=3CN(CC=3N=2)C(O)=O)CC1 AQDJBCDVWZZKAJ-UHFFFAOYSA-N 0.000 claims description 3
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 3
- 206010069632 Bladder dysfunction Diseases 0.000 claims description 3
- 201000004624 Dermatitis Diseases 0.000 claims description 3
- 208000034347 Faecal incontinence Diseases 0.000 claims description 3
- 208000014540 Functional gastrointestinal disease Diseases 0.000 claims description 3
- 206010020751 Hypersensitivity Diseases 0.000 claims description 3
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 3
- 206010046543 Urinary incontinence Diseases 0.000 claims description 3
- 208000026935 allergic disease Diseases 0.000 claims description 3
- 230000001363 autoimmune Effects 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 201000007637 bowel dysfunction Diseases 0.000 claims description 3
- 208000015114 central nervous system disease Diseases 0.000 claims description 3
- 230000003111 delayed effect Effects 0.000 claims description 3
- 230000009610 hypersensitivity Effects 0.000 claims description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 230000027939 micturition Effects 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- OCYUDLLSFWBUTB-UHFFFAOYSA-N n-(5-tert-butyl-2-methylphenyl)-2-[4-(4-methoxyphenyl)piperazin-1-yl]-6-methylsulfonyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2N=C(NC=3C(=CC=C(C=3)C(C)(C)C)C)C=3CN(CC=3N=2)S(C)(=O)=O)CC1 OCYUDLLSFWBUTB-UHFFFAOYSA-N 0.000 claims description 3
- GQGKAYQOCFXYLK-UHFFFAOYSA-N n-[6-[(3-methoxyphenyl)methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound COC1=CC=CC(CN2CC3=C(NC=4C=C5C=CC=CC5=NC=4)N=CN=C3C2)=C1 GQGKAYQOCFXYLK-UHFFFAOYSA-N 0.000 claims description 3
- AUHAJHZEHLPERZ-UHFFFAOYSA-N n-[6-[[2-(difluoromethoxy)phenyl]methyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound FC(F)OC1=CC=CC=C1CN1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 AUHAJHZEHLPERZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 210000002307 prostate Anatomy 0.000 claims description 3
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 208000036273 reactive airway disease Diseases 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- MWXCMAMFVKPIAB-UHFFFAOYSA-N (2,4-dimethyl-1,3-thiazol-5-yl)-[4-(quinolin-3-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidin-6-yl]methanone Chemical compound S1C(C)=NC(C)=C1C(=O)N1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 MWXCMAMFVKPIAB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004463 2,4-dimethyl-thiazol-5-yl group Chemical group CC=1SC(=C(N1)C)* 0.000 claims description 2
- JAKPSIHJIICGQS-UHFFFAOYSA-N 2-(azepan-1-yl)-1-[4-(quinolin-3-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidin-6-yl]ethanone Chemical compound C1C2=NC=NC(NC=3C=C4C=CC=CC4=NC=3)=C2CN1C(=O)CN1CCCCCC1 JAKPSIHJIICGQS-UHFFFAOYSA-N 0.000 claims description 2
- VWJTZPIPBDLDMU-UHFFFAOYSA-N 2-piperidin-1-yl-1-[4-(quinolin-3-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidin-6-yl]ethanone Chemical compound C1C2=NC=NC(NC=3C=C4C=CC=CC4=NC=3)=C2CN1C(=O)CN1CCCCC1 VWJTZPIPBDLDMU-UHFFFAOYSA-N 0.000 claims description 2
- LDSNHRPELMFACU-UHFFFAOYSA-N 2-pyrrolidin-1-yl-1-[4-(quinolin-3-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidin-6-yl]ethanone Chemical compound C1C2=NC=NC(NC=3C=C4C=CC=CC4=NC=3)=C2CN1C(=O)CN1CCCC1 LDSNHRPELMFACU-UHFFFAOYSA-N 0.000 claims description 2
- WITJHZRCLVXYCA-UHFFFAOYSA-N 3h-1,2-benzodioxepine Chemical class C1=CCOOC2=CC=CC=C21 WITJHZRCLVXYCA-UHFFFAOYSA-N 0.000 claims description 2
- KQEGVJZXNYPBLY-UHFFFAOYSA-N 4-[4-(quinolin-3-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidin-6-yl]butan-1-ol Chemical compound C1=CC=CC2=CC(NC=3N=CN=C4CN(CC4=3)CCCCO)=CN=C21 KQEGVJZXNYPBLY-UHFFFAOYSA-N 0.000 claims description 2
- 208000020084 Bone disease Diseases 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical group CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
- 150000005528 benzodioxoles Chemical class 0.000 claims description 2
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- PQIHHBPAEPMKTE-UHFFFAOYSA-N methyl 2-methyl-5-[[4-(quinolin-3-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidin-6-yl]sulfonyl]furan-3-carboxylate Chemical compound O1C(C)=C(C(=O)OC)C=C1S(=O)(=O)N1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 PQIHHBPAEPMKTE-UHFFFAOYSA-N 0.000 claims description 2
- FKRXKUGKGYCEGN-UHFFFAOYSA-N n-(2,4-dimethyl-1,3-thiazol-5-yl)-4-(quinolin-3-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxamide Chemical compound S1C(C)=NC(C)=C1NC(=O)N1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 FKRXKUGKGYCEGN-UHFFFAOYSA-N 0.000 claims description 2
- JHODPUGXTPQSKP-UHFFFAOYSA-N n-(6-benzylsulfonyl-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)CC1=CC=CC=C1 JHODPUGXTPQSKP-UHFFFAOYSA-N 0.000 claims description 2
- AGLWWAKTGWSEDK-UHFFFAOYSA-N n-(6-butan-2-yl-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl)quinolin-3-amine Chemical compound C1=CC=CC2=CC(NC=3N=CN=C4CN(CC4=3)C(C)CC)=CN=C21 AGLWWAKTGWSEDK-UHFFFAOYSA-N 0.000 claims description 2
- TVSJNUISMPIPIK-UHFFFAOYSA-N n-(6-butyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl)quinolin-3-amine Chemical compound C1=CC=CC2=CC(NC=3N=CN=C4CN(CC4=3)CCCC)=CN=C21 TVSJNUISMPIPIK-UHFFFAOYSA-N 0.000 claims description 2
- GEYRNFCTFKVABI-UHFFFAOYSA-N n-(6-cyclobutyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl)quinolin-3-amine Chemical compound C1CCC1N1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 GEYRNFCTFKVABI-UHFFFAOYSA-N 0.000 claims description 2
- RIPANCXYWIEXOF-UHFFFAOYSA-N n-(6-cycloheptyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl)quinolin-3-amine Chemical compound C1C(C(=NC=N2)NC=3C=C4C=CC=CC4=NC=3)=C2CN1C1CCCCCC1 RIPANCXYWIEXOF-UHFFFAOYSA-N 0.000 claims description 2
- MDJWBVYCOZVCDY-UHFFFAOYSA-N n-(6-cyclohexyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl)quinolin-3-amine Chemical compound C1C(C(=NC=N2)NC=3C=C4C=CC=CC4=NC=3)=C2CN1C1CCCCC1 MDJWBVYCOZVCDY-UHFFFAOYSA-N 0.000 claims description 2
- ZDGTXZCZZCMDCT-UHFFFAOYSA-N n-(6-cyclohexylsulfonyl-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)C1CCCCC1 ZDGTXZCZZCMDCT-UHFFFAOYSA-N 0.000 claims description 2
- HEPXZSAFSQULGQ-UHFFFAOYSA-N n-(6-cyclopentyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl)quinolin-3-amine Chemical compound C1CCCC1N1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 HEPXZSAFSQULGQ-UHFFFAOYSA-N 0.000 claims description 2
- OFQIFIRPICEJLR-UHFFFAOYSA-N n-(6-cyclopentylsulfonyl-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)C1CCCC1 OFQIFIRPICEJLR-UHFFFAOYSA-N 0.000 claims description 2
- SZPTYZSZHKHSMB-UHFFFAOYSA-N n-(6-ethyl-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)=CN=C21 SZPTYZSZHKHSMB-UHFFFAOYSA-N 0.000 claims description 2
- PPPBZQMYSLJHBO-UHFFFAOYSA-N n-(6-pentan-2-yl-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl)quinolin-3-amine Chemical compound C1=CC=CC2=CC(NC=3N=CN=C4CN(CC4=3)C(C)CCC)=CN=C21 PPPBZQMYSLJHBO-UHFFFAOYSA-N 0.000 claims description 2
- LHPBHMIYNQHODL-UHFFFAOYSA-N n-(6-pentyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl)quinolin-3-amine Chemical compound C1=CC=CC2=CC(NC=3N=CN=C4CN(CC4=3)CCCCC)=CN=C21 LHPBHMIYNQHODL-UHFFFAOYSA-N 0.000 claims description 2
- RTJCGMFJSUAXEG-UHFFFAOYSA-N n-(6-propan-2-yl-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl)quinolin-3-amine Chemical compound C1=CC=CC2=CC(NC=3N=CN=C4CN(CC4=3)C(C)C)=CN=C21 RTJCGMFJSUAXEG-UHFFFAOYSA-N 0.000 claims description 2
- MTVUTKQZHIDUNW-UHFFFAOYSA-N n-(6-propyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl)quinolin-3-amine Chemical compound C1=CC=CC2=CC(NC=3N=CN=C4CN(CC4=3)CCC)=CN=C21 MTVUTKQZHIDUNW-UHFFFAOYSA-N 0.000 claims description 2
- CBPHGSKWPDZFTJ-UHFFFAOYSA-N n-(cyclohexylmethyl)-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)NCC1CCCCC1 CBPHGSKWPDZFTJ-UHFFFAOYSA-N 0.000 claims description 2
- ZBHBDQMASSYGAF-UHFFFAOYSA-N n-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-4-(quinolin-3-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxamide Chemical compound S1C(C)=NC(C)=C1CNC(=O)N1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 ZBHBDQMASSYGAF-UHFFFAOYSA-N 0.000 claims description 2
- CMGQFNBUJLUYDE-UHFFFAOYSA-N n-[6-(1,3-thiazol-2-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=NC=CS1 CMGQFNBUJLUYDE-UHFFFAOYSA-N 0.000 claims description 2
- XFWMSEQQFLCWGQ-UHFFFAOYSA-N n-[6-(1,3-thiazol-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=CSC=N1 XFWMSEQQFLCWGQ-UHFFFAOYSA-N 0.000 claims description 2
- WYUQUIJQTCPKJF-UHFFFAOYSA-N n-[6-(1,3-thiazol-5-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=CN=CS1 WYUQUIJQTCPKJF-UHFFFAOYSA-N 0.000 claims description 2
- WJPCTEAQERTMRF-UHFFFAOYSA-N n-[6-(1-cyclobutylethyl)-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)C1CCC1 WJPCTEAQERTMRF-UHFFFAOYSA-N 0.000 claims description 2
- IJLGUCCVIIHGJI-UHFFFAOYSA-N n-[6-(2,2,2-trifluoroethyl)-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(F)(F)F)=CN=C21 IJLGUCCVIIHGJI-UHFFFAOYSA-N 0.000 claims description 2
- UXDITVUAJDFDDC-UHFFFAOYSA-N n-[6-(2,2-dimethylpropyl)-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(C)(C)C)=CN=C21 UXDITVUAJDFDDC-UHFFFAOYSA-N 0.000 claims description 2
- BMZKBWKAHPLKEI-UHFFFAOYSA-N n-[6-(2,4-difluorophenyl)sulfonyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound FC1=CC(F)=CC=C1S(=O)(=O)N1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 BMZKBWKAHPLKEI-UHFFFAOYSA-N 0.000 claims description 2
- DMPIYOSAHISXHP-UHFFFAOYSA-N n-[6-(2-chlorophenyl)sulfonyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound ClC1=CC=CC=C1S(=O)(=O)N1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 DMPIYOSAHISXHP-UHFFFAOYSA-N 0.000 claims description 2
- MXLGUUWMBKYOQC-UHFFFAOYSA-N n-[6-(2-methoxyphenyl)sulfonyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound COC1=CC=CC=C1S(=O)(=O)N1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 MXLGUUWMBKYOQC-UHFFFAOYSA-N 0.000 claims description 2
- PPFMKSCANOQUFI-UHFFFAOYSA-N n-[6-(2-methylbutyl)-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(C)CC)=CN=C21 PPFMKSCANOQUFI-UHFFFAOYSA-N 0.000 claims description 2
- VBVQOUCYQYKYRU-UHFFFAOYSA-N n-[6-(2-methylpropyl)-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(C)C)=CN=C21 VBVQOUCYQYKYRU-UHFFFAOYSA-N 0.000 claims description 2
- FSDTYBRZLNEJJC-UHFFFAOYSA-N n-[6-(2-methylpyrazol-3-yl)sulfonyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound CN1N=CC=C1S(=O)(=O)N1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 FSDTYBRZLNEJJC-UHFFFAOYSA-N 0.000 claims description 2
- YLFJCBXEEOHOMW-UHFFFAOYSA-N n-[6-(2-phenylethylsulfonyl)-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)CCC1=CC=CC=C1 YLFJCBXEEOHOMW-UHFFFAOYSA-N 0.000 claims description 2
- WMAZBWXVLXEOPY-UHFFFAOYSA-N n-[6-(3,3,3-trifluoropropyl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1=CC=CC2=CC(NC=3N=CN=C4CN(CC4=3)CCC(F)(F)F)=CN=C21 WMAZBWXVLXEOPY-UHFFFAOYSA-N 0.000 claims description 2
- BRVKYOMVIRPLRT-UHFFFAOYSA-N n-[6-(3,3-dimethylbutyl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1=CC=CC2=CC(NC=3N=CN=C4CN(CC4=3)CCC(C)(C)C)=CN=C21 BRVKYOMVIRPLRT-UHFFFAOYSA-N 0.000 claims description 2
- BNKAZTYSIZSABU-UHFFFAOYSA-N n-[6-(3-methylbutan-2-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1=CC=CC2=CC(NC=3N=CN=C4CN(CC4=3)C(C)C(C)C)=CN=C21 BNKAZTYSIZSABU-UHFFFAOYSA-N 0.000 claims description 2
- PKHQWQLMXMMCNX-UHFFFAOYSA-N n-[6-(3-methylthiophen-2-yl)sulfonyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1=CSC(S(=O)(=O)N2CC3=C(NC=4C=C5C=CC=CC5=NC=4)N=CN=C3C2)=C1C PKHQWQLMXMMCNX-UHFFFAOYSA-N 0.000 claims description 2
- WMCJYWUGYVHQJI-UHFFFAOYSA-N n-[6-(4,4-dimethylpentan-2-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1=CC=CC2=CC(NC=3N=CN=C4CN(CC4=3)C(CC(C)(C)C)C)=CN=C21 WMCJYWUGYVHQJI-UHFFFAOYSA-N 0.000 claims description 2
- AWBJYDLMGQUZGG-UHFFFAOYSA-N n-[6-(benzenesulfonyl)-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)C1=CC=CC=C1 AWBJYDLMGQUZGG-UHFFFAOYSA-N 0.000 claims description 2
- HSUBPDSOOAPXPK-UHFFFAOYSA-N n-[6-(cyclobutylmethyl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1C2=NC=NC(NC=3C=C4C=CC=CC4=NC=3)=C2CN1CC1CCC1 HSUBPDSOOAPXPK-UHFFFAOYSA-N 0.000 claims description 2
- DHEIBNIGOARORF-UHFFFAOYSA-N n-[6-(cyclopropylmethyl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1C2=NC=NC(NC=3C=C4C=CC=CC4=NC=3)=C2CN1CC1CC1 DHEIBNIGOARORF-UHFFFAOYSA-N 0.000 claims description 2
- IWUUHFDQZMYLDC-UHFFFAOYSA-N n-[6-(oxan-3-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)=C2CN1CC1CCCOC1 IWUUHFDQZMYLDC-UHFFFAOYSA-N 0.000 claims description 2
- QBAZAWJFWWYYRP-UHFFFAOYSA-N n-[6-(oxetan-3-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1OCC1N1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 QBAZAWJFWWYYRP-UHFFFAOYSA-N 0.000 claims description 2
- YGORJUPDMNFEEE-UHFFFAOYSA-N n-[6-(oxolan-3-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)=C2CN1CC1CCOC1 YGORJUPDMNFEEE-UHFFFAOYSA-N 0.000 claims description 2
- XKMHCMZOISUWHN-UHFFFAOYSA-N n-[6-(quinolin-4-ylmethyl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound C1=CC=C2C(CN3CC4=C(NC=5C=C6C=CC=CC6=NC=5)N=CN=C4C3)=CC=NC2=C1 XKMHCMZOISUWHN-UHFFFAOYSA-N 0.000 claims description 2
- 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
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 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
- 201000006370 kidney failure Diseases 0.000 claims 1
- FFQSDSUMXOLVPN-UHFFFAOYSA-N n-[6-[2-(trifluoromethoxy)phenyl]sulfonyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound FC(F)(F)OC1=CC=CC=C1S(=O)(=O)N1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 FFQSDSUMXOLVPN-UHFFFAOYSA-N 0.000 claims 1
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 description 9
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 0 CC1(*)/C=N/C=C/*(CN(C2)Cc3c2c(Nc2cc(cccc4)c4nc2)ncn3)/C=C1 Chemical compound CC1(*)/C=N/C=C/*(CN(C2)Cc3c2c(Nc2cc(cccc4)c4nc2)ncn3)/C=C1 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000006217 methyl sulfide group Chemical group [H]C([H])([H])S* 0.000 description 3
- 102100027297 Fatty acid 2-hydroxylase Human genes 0.000 description 2
- 101000937693 Homo sapiens Fatty acid 2-hydroxylase Proteins 0.000 description 2
- 101000918494 Homo sapiens Fatty-acid amide hydrolase 1 Proteins 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
- 206010000117 Abnormal behaviour Diseases 0.000 description 1
- 206010012335 Dependence Diseases 0.000 description 1
- 229940096895 Dopamine D2 receptor agonist Drugs 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 239000002288 dopamine 2 receptor stimulating agent Substances 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- ZLWPFJYFMGAWHW-UHFFFAOYSA-N n-[6-(2-fluorophenyl)sulfonyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]quinolin-3-amine Chemical compound FC1=CC=CC=C1S(=O)(=O)N1CC2=C(NC=3C=C4C=CC=CC4=NC=3)N=CN=C2C1 ZLWPFJYFMGAWHW-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
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 (enExample) | 2012-11-22 |
| JP5539376B2 JP5539376B2 (ja) | 2014-07-02 |
Family
ID=41786362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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)
| Country | Link |
|---|---|
| US (1) | US20110257208A1 (enExample) |
| EP (1) | EP2364316A1 (enExample) |
| JP (1) | JP5539376B2 (enExample) |
| CA (1) | CA2744343A1 (enExample) |
| WO (1) | WO2010059610A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130150346A1 (en) | 2010-01-08 | 2013-06-13 | Quest Ventures Ltd. | 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 |
| CN109045032A (zh) | 2014-01-01 | 2018-12-21 | 麦迪威森技术有限责任公司 | 氨基吡啶类化合物和使用方法 |
| KR20240167846A (ko) | 2022-03-28 | 2024-11-28 | 니캉 테라퓨틱스 인코포레이티드 | 사이클린 의존적 키나제 2 억제제로서의 설폰아미도 유도체 |
| US20260048062A1 (en) * | 2024-03-06 | 2026-02-19 | Ovid Therapeutics Inc. | Fused amino pyrimidine compounds for treatment of psychosis and psychotic disorders |
| WO2025188973A1 (en) * | 2024-03-06 | 2025-09-12 | Ovid Therapeutics Inc. | Fused amino pyrimidine compounds for treatment of 22q11.2 deletion/duplication syndromes |
| 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 |
| WO2025188977A1 (en) * | 2024-03-06 | 2025-09-12 | Ovid Therapeutics Inc. | Fused amino pyrimidine compounds for treatment of addiction and insomnia |
| US20250281497A1 (en) * | 2024-03-06 | 2025-09-11 | Ovid Therapeutics Inc. | Fused amino pyrimidine compounds for treatment of seizure disorders |
| WO2025188952A1 (en) * | 2024-03-06 | 2025-09-12 | Ovid Therapeutics Inc. | Fused amino pyrimidine compounds for treatment of synucleinopathies and tdp-43 proteinopathies |
| WO2025188953A1 (en) * | 2024-03-06 | 2025-09-12 | Ovid Therapeutics Inc. | Fused amino pyrimidine compounds for treatment of neuropathic and neuro-inflammatory pain |
| US20250281500A1 (en) * | 2024-03-06 | 2025-09-11 | Ovid Therapeutics Inc. | Fused amino pyrimidine compounds and pridopidine for treatment of huntington’s disease |
| US20260048063A1 (en) * | 2024-03-06 | 2026-02-19 | Ovid Therapeutics Inc. | Fused amino pyrimidine compounds for treatment of neurodegenerative disorders |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU1071301A (en) * | 1999-11-01 | 2001-05-14 | Eli Lilly And Company | Pharmaceutical compounds |
| ES2266258T3 (es) * | 2000-09-15 | 2007-03-01 | Vertex Pharmaceuticals Incorporated | Compuestos de pirazol utiles como inhibidores de proteina cinasas. |
| 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 |
| EP2121633A2 (en) * | 2007-02-12 | 2009-11-25 | 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 |
| RU2011116928A (ru) * | 2008-09-30 | 2012-11-20 | Астразенека Аб (Se) | Гетероциклические ингибиторы jак киназы |
-
2009
- 2009-11-17 WO PCT/US2009/064757 patent/WO2010059610A1/en not_active Ceased
- 2009-11-17 US US13/130,051 patent/US20110257208A1/en not_active Abandoned
- 2009-11-17 EP EP09793640A patent/EP2364316A1/en not_active Withdrawn
- 2009-11-17 JP JP2011537547A patent/JP5539376B2/ja not_active Expired - Fee Related
- 2009-11-17 CA CA2744343A patent/CA2744343A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4287146B2 (ja) | トリアゾロ［４，５−ｄ］ピリミジン誘導体およびプリン作用性レセプターアンタゴニストとしてのこれらの使用 | |
| US8906914B2 (en) | Ethylene diamine modulators of fatty acid hydrolase | |
| JP4346269B2 (ja) | Ａ２ａレセプターアンタゴニストとしてのチエノおよびフロピリミジン誘導体 | |
| CN104327084B (zh) | Bcr‑abl的小分子豆蔻酸酯抑制剂及其使用方法 | |
| KR101962488B1 (ko) | 치환된 디아미노카르복스아미드 및 디아미노카르보니트릴 피리미딘, 그의 조성물, 및 그를 사용하는 치료 방법 | |
| US7098333B2 (en) | Pyrrolo[2,3-d]pyrimidine and their use as purinergic receptor antagonists | |
| JP4284069B2 (ja) | プリン作動性レセプターアンタゴニストとしてのプリン誘導体 | |
| JP2011500657A (ja) | 組合せ０５９ | |
| JP2021500340A5 (enExample) | ||
| JP2012502986A5 (enExample) | ||
| IL226912A (en) | The history of triazole, their preparation and their pharmaceutical preparations | |
| RU2008132802A (ru) | Новые производные тиофена в качестве агонистов рецептора s1p1/edg1 | |
| JP2008538544A (ja) | 新規ピリミジン化合物、それらの調製のためのプロセスおよびそれらを含む組成物 | |
| JP2004517861A (ja) | プリン作動性レセプターアンタゴニストとしてのピラゾロ［３，４−ｄ］ピリミジン誘導体およびそれらの使用 | |
| CA2672591A1 (en) | Treating agent of uropathy | |
| JP2016519659A (ja) | 軟骨形成を誘導するための化合物及び方法 | |
| JP2008511670A5 (enExample) | ||
| CN108368060B (zh) | 一类嘧啶类衍生物激酶抑制剂 | |
| ZA200606243B (en) | Imidazolo-5-yl-2-anilinopyrimidines as agents for the inhibition of cell proliferation | |
| JP2004513966A (ja) | チエノピリミジン類の使用 | |
| JP2002533318A (ja) | イオンチャネル調節剤 | |
| CN101959855A (zh) | 氮杂环丁烷衍生化合物、其制备方法和其治疗用途 | |
| WO2019034153A1 (zh) | 一种化合物，其药物组合物及其用途及应用 | |
| JP2009523842A (ja) | ナトリウムチャネルモジュレーターとしてのピリジン誘導体 | |
| CN111892592B (zh) | Jak激酶抑制剂及其用途 |