CA2744343A1

CA2744343A1 - 6, 7 -dihydro- 5h- pyrrolo [3, 4-d] pyrimidin-4-yl] -quinolin-3 -ylamine compounds useful as faah modulators and uses thereof

6, 7 -dihydro- 5h- pyrrolo [3, 4-d] pyrimidin-4-yl] -quinolin-3 -ylamine compounds useful as faah modulators and uses thereof Download PDF

Info

Publication number: CA2744343A1
Authority: CA; Canada
Prior art keywords: dihydro; pyrrolo; quinolin; pyrimidin; amine
Prior art date: 2008-11-19
Legal status : Abandoned

Application number

CA2744343A

Other languages

English (en)

French (fr)

Inventor

Matthew Duncton

Donogh John Roger O'mahony

Matthew Cox

Current Assignee

Evotec US Inc

Original Assignee

Renovis Inc

Priority date

2008-11-19

Filing date

2009-11-17

Publication date

2010-05-27

2009-11-17 Application filed by Renovis Inc filed Critical Renovis Inc

2010-05-27 Publication of CA2744343A1 publication Critical patent/CA2744343A1/en

Status Abandoned legal-status Critical Current

Links

125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 title description 3
101150042613 FA2H gene Proteins 0.000 title 1
101150008770 FAAH gene Proteins 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 479
208000002193 Pain Diseases 0.000 claims abstract description 40
238000011282 treatment Methods 0.000 claims abstract description 34
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 33
230000036407 pain Effects 0.000 claims abstract description 32
208000019901 Anxiety disease Diseases 0.000 claims abstract description 19
230000036506 anxiety Effects 0.000 claims abstract description 19
208000008238 Muscle Spasticity Diseases 0.000 claims abstract description 17
208000018198 spasticity Diseases 0.000 claims abstract description 17
208000018737 Parkinson disease Diseases 0.000 claims abstract description 16
206010061218 Inflammation Diseases 0.000 claims abstract description 14
230000004054 inflammatory process Effects 0.000 claims abstract description 14
241000124008 Mammalia Species 0.000 claims abstract description 13
208000030814 Eating disease Diseases 0.000 claims abstract description 12
208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 12
235000014632 disordered eating Nutrition 0.000 claims abstract description 12
206010012335 Dependence Diseases 0.000 claims abstract description 10
208000010412 Glaucoma Diseases 0.000 claims abstract description 10
208000024827 Alzheimer disease Diseases 0.000 claims abstract description 9
208000010877 cognitive disease Diseases 0.000 claims abstract description 8
230000002265 prevention Effects 0.000 claims abstract description 8
-1 azido, carboxy Chemical group 0.000 claims description 237
125000003118 aryl group Chemical group 0.000 claims description 138
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 93
125000000217 alkyl group Chemical group 0.000 claims description 91
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 91
125000001424 substituent group Chemical group 0.000 claims description 84
125000003545 alkoxy group Chemical group 0.000 claims description 78
238000000034 method Methods 0.000 claims description 75
125000001072 heteroaryl group Chemical group 0.000 claims description 68
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 66
125000003710 aryl alkyl group Chemical group 0.000 claims description 56
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 48
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 48
125000001188 haloalkyl group Chemical group 0.000 claims description 42
201000010099 disease Diseases 0.000 claims description 38
125000003226 pyrazolyl group Chemical group 0.000 claims description 36
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
125000003396 thiol group Chemical group [H]S* 0.000 claims description 35
229910052739 hydrogen Inorganic materials 0.000 claims description 34
150000003839 salts Chemical class 0.000 claims description 33
125000002252 acyl group Chemical group 0.000 claims description 32
125000000335 thiazolyl group Chemical group 0.000 claims description 32
125000004076 pyridyl group Chemical group 0.000 claims description 31
125000004438 haloalkoxy group Chemical group 0.000 claims description 30
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 29
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 29
208000035475 disorder Diseases 0.000 claims description 28
239000001257 hydrogen Substances 0.000 claims description 28
239000012453 solvate Substances 0.000 claims description 28
125000002541 furyl group Chemical group 0.000 claims description 27
239000000651 prodrug Substances 0.000 claims description 27
229940002612 prodrug Drugs 0.000 claims description 27
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 26
229910052731 fluorine Inorganic materials 0.000 claims description 25
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 25
125000001113 thiadiazolyl group Chemical group 0.000 claims description 25
125000001544 thienyl group Chemical group 0.000 claims description 25
230000000694 effects Effects 0.000 claims description 24
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 24
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 23
125000004093 cyano group Chemical group *C#N 0.000 claims description 23
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 23
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 20
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
125000001715 oxadiazolyl group Chemical group 0.000 claims description 19
125000000168 pyrrolyl group Chemical group 0.000 claims description 19
JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 18
108010081348 HRT1 protein Hairy Proteins 0.000 claims description 18
102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 18
125000004442 acylamino group Chemical group 0.000 claims description 18
229910052801 chlorine Inorganic materials 0.000 claims description 18
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 17
230000000155 isotopic effect Effects 0.000 claims description 17
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 16
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 16
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
230000001404 mediated effect Effects 0.000 claims description 16
208000037765 diseases and disorders Diseases 0.000 claims description 15
125000002883 imidazolyl group Chemical group 0.000 claims description 15
208000023275 Autoimmune disease Diseases 0.000 claims description 14
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 14
125000002971 oxazolyl group Chemical group 0.000 claims description 14
125000003107 substituted aryl group Chemical group 0.000 claims description 14
125000003342 alkenyl group Chemical group 0.000 claims description 13
125000003368 amide group Chemical group 0.000 claims description 13
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 13
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 13
125000000304 alkynyl group Chemical group 0.000 claims description 12
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 12
125000005553 heteroaryloxy group Chemical group 0.000 claims description 12
125000002757 morpholinyl group Chemical group 0.000 claims description 12
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
125000004193 piperazinyl group Chemical group 0.000 claims description 12
125000003386 piperidinyl group Chemical group 0.000 claims description 12
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 12
229910006069 SO3H Inorganic materials 0.000 claims description 11
RMGVZKRVHHSUIM-UHFFFAOYSA-N dithionic acid Chemical compound OS(=O)(=O)S(O)(=O)=O RMGVZKRVHHSUIM-UHFFFAOYSA-N 0.000 claims description 11
206010015037 epilepsy Diseases 0.000 claims description 11
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 11
125000006217 methyl sulfide group Chemical group [H]C([H])([H])S* 0.000 claims description 11
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 11
208000015122 neurodegenerative disease Diseases 0.000 claims description 11
150000003456 sulfonamides Chemical class 0.000 claims description 11
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 11
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 10
208000003251 Pruritus Diseases 0.000 claims description 10
206010047700 Vomiting Diseases 0.000 claims description 10
230000006399 behavior Effects 0.000 claims description 10
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 10
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 10
125000001041 indolyl group Chemical group 0.000 claims description 10
150000002632 lipids Chemical class 0.000 claims description 10
208000004296 neuralgia Diseases 0.000 claims description 10
208000023504 respiratory system disease Diseases 0.000 claims description 10
208000019116 sleep disease Diseases 0.000 claims description 10
229940124530 sulfonamide Drugs 0.000 claims description 10
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 9
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 9
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 9
208000021722 neuropathic pain Diseases 0.000 claims description 9
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 9
125000005017 substituted alkenyl group Chemical group 0.000 claims description 9
125000004426 substituted alkynyl group Chemical group 0.000 claims description 9
208000006673 asthma Diseases 0.000 claims description 8
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
238000001727 in vivo Methods 0.000 claims description 8
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 8
201000006417 multiple sclerosis Diseases 0.000 claims description 8
208000010125 myocardial infarction Diseases 0.000 claims description 8
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 8
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 8
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 8
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 8
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 8
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 8
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 8
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 8
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 8
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 8
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 8
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 8
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 8
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 8
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 8
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 8
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 8
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 8
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 8
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 8
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 8
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 8
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 8
125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
125000001425 triazolyl group Chemical group 0.000 claims description 8
206010065390 Inflammatory pain Diseases 0.000 claims description 7
206010028813 Nausea Diseases 0.000 claims description 7
206010028980 Neoplasm Diseases 0.000 claims description 7
201000011510 cancer Diseases 0.000 claims description 7
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 7
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 7
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 7
230000008693 nausea Effects 0.000 claims description 7
230000004770 neurodegeneration Effects 0.000 claims description 7
201000000980 schizophrenia Diseases 0.000 claims description 7
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
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 6
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 6
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 6
208000008589 Obesity Diseases 0.000 claims description 6
206010003246 arthritis Diseases 0.000 claims description 6
208000017169 kidney disease Diseases 0.000 claims description 6
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