EA025186B1 - НОВЫЕ 4-(ЗАМЕЩЕННЫЙ АМИНО)-7Н-ПИРРОЛО[2,3-d]ПИРИМИДИНЫ В КАЧЕСТВЕ ИНГИБИТОРОВ LRRK2 - Google Patents

Info

Publication number

EA025186B1

EA025186B1 EA201492125A EA201492125A EA025186B1 EA 025186 B1 EA025186 B1 EA 025186B1 EA 201492125 A EA201492125 A EA 201492125A EA 201492125 A EA201492125 A EA 201492125A EA 025186 B1 EA025186 B1 EA 025186B1

Authority

EA

Eurasian Patent Office

Prior art keywords

pyrrolo

pyrimidin

morpholin

benzonitrile

pyrimidine

Prior art date

2012-06-29

Links

• Espacenet
• Global Dossier
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• 229940124786 LRRK2 inhibitor Drugs 0.000 title 1
• -1 4,5-disubstituted-7H-pyrrolo[2,3-d]pyrimidine Chemical class 0.000 claims abstract description 432
• 150000001875 compounds Chemical class 0.000 claims abstract description 221
• 150000003839 salts Chemical class 0.000 claims abstract description 67
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 27
• 208000018737 Parkinson disease Diseases 0.000 claims abstract description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 880
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 406
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 366
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 304
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 110
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 49
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 38
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
• 229910052757 nitrogen Inorganic materials 0.000 claims description 32
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 31
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 28
• 125000005842 heteroatom Chemical group 0.000 claims description 28
• FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims description 23
• OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 22
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 18
• 108091000080 Phosphotransferase Proteins 0.000 claims description 18
• 102000020233 phosphotransferase Human genes 0.000 claims description 18
• 239000001257 hydrogen Substances 0.000 claims description 17
• 229910052739 hydrogen Inorganic materials 0.000 claims description 17
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• 150000002367 halogens Chemical class 0.000 claims description 15
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 14
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 13
• BIWOSRSKDCZIFM-UHFFFAOYSA-N piperidin-3-ol Chemical compound OC1CCCNC1 BIWOSRSKDCZIFM-UHFFFAOYSA-N 0.000 claims description 13
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• 239000003814 drug Substances 0.000 claims description 10
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 8
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 6
• BVOCPVIXARZNQN-UHFFFAOYSA-N nipecotamide Chemical compound NC(=O)C1CCCNC1 BVOCPVIXARZNQN-UHFFFAOYSA-N 0.000 claims description 6
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• CUPOOAWTRIURFT-UHFFFAOYSA-N thiophene-2-carbonitrile Chemical compound N#CC1=CC=CS1 CUPOOAWTRIURFT-UHFFFAOYSA-N 0.000 claims description 6
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 5
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 5
• 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims description 4
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000004486 1-methylpiperidin-3-yl group Chemical group CN1CC(CCC1)* 0.000 claims description 3
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 3
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 3
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• 239000005711 Benzoic acid Substances 0.000 claims description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
• 235000010233 benzoic acid Nutrition 0.000 claims description 3
• 239000000460 chlorine Substances 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 3
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 3
• HAASCECTXNYFCI-UHFFFAOYSA-N morpholine-2-carbonitrile Chemical compound N#CC1CNCCO1 HAASCECTXNYFCI-UHFFFAOYSA-N 0.000 claims description 3
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 3
• ZGNXATVKGIJQGC-UHFFFAOYSA-N piperidine-3-carbonitrile Chemical compound N#CC1CCCNC1 ZGNXATVKGIJQGC-UHFFFAOYSA-N 0.000 claims description 3
• 125000003386 piperidinyl group Chemical group 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims description 3
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
• WOWULVZMWDEPKC-UHFFFAOYSA-N 4-[5-(2-chloro-3-fluoro-6-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CC=C(F)C(Cl)=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 WOWULVZMWDEPKC-UHFFFAOYSA-N 0.000 claims description 2
• 210000004901 leucine-rich repeat Anatomy 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 2
• PLQIAEXRNLFVCU-UHFFFAOYSA-N 1-[5-(2-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]piperidin-3-ol Chemical compound COC1=CC=CC=C1C1=CNC2=NC=NC(N3CC(O)CCC3)=C12 PLQIAEXRNLFVCU-UHFFFAOYSA-N 0.000 claims 1
• MRABRFBCPPKJLC-UHFFFAOYSA-N 1-[5-(3-fluoro-5-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]piperidin-3-ol Chemical compound COC1=CC(F)=CC(C=2C3=C(N4CC(O)CCC4)N=CN=C3NC=2)=C1 MRABRFBCPPKJLC-UHFFFAOYSA-N 0.000 claims 1
• BEHWSSWEKOLCEQ-UHFFFAOYSA-N 1-[5-(3-fluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]piperidin-3-ol Chemical compound C1C(O)CCCN1C1=NC=NC2=C1C(C=1C=C(F)C=CC=1)=CN2 BEHWSSWEKOLCEQ-UHFFFAOYSA-N 0.000 claims 1
• PQXAADSTABWHNC-UHFFFAOYSA-N 1-[5-(5-methylpyridin-3-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]piperidin-3-ol Chemical compound CC1=CN=CC(C=2C3=C(N4CC(O)CCC4)N=CN=C3NC=2)=C1 PQXAADSTABWHNC-UHFFFAOYSA-N 0.000 claims 1
• AFVZXTFKZIXUDK-UHFFFAOYSA-N 2-fluoro-3-(2-methyl-4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound C=12C(C=3C(=C(C#N)C=CC=3)F)=CNC2=NC(C)=NC=1N1CCOCC1 AFVZXTFKZIXUDK-UHFFFAOYSA-N 0.000 claims 1
• QYKISUPBXOHKOJ-UHFFFAOYSA-N 2-fluoro-3-(4-pyrrolidin-1-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound FC1=C(C#N)C=CC=C1C1=CNC2=NC=NC(N3CCCC3)=C12 QYKISUPBXOHKOJ-UHFFFAOYSA-N 0.000 claims 1
• WXQULZKGDNSDIT-UHFFFAOYSA-N 2-fluoro-3-[4-(3-hydroxypiperidin-1-yl)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1C(O)CCCN1C1=NC=NC2=C1C(C=1C(=C(C#N)C=CC=1)F)=CN2 WXQULZKGDNSDIT-UHFFFAOYSA-N 0.000 claims 1
• AHNKWHJBFLDDJQ-UHFFFAOYSA-N 2-fluoro-3-[4-(4-fluoropiperidin-1-yl)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1CC(F)CCN1C1=NC=NC2=C1C(C=1C(=C(C#N)C=CC=1)F)=CN2 AHNKWHJBFLDDJQ-UHFFFAOYSA-N 0.000 claims 1
• GTPYPGWTKZAMCX-UHFFFAOYSA-N 2-fluoro-3-[4-[2-(3-methyl-1,2,4-oxadiazol-5-yl)morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound CC1=NOC(C2OCCN(C2)C=2C=3C(C=4C(=C(C#N)C=CC=4)F)=CNC=3N=CN=2)=N1 GTPYPGWTKZAMCX-UHFFFAOYSA-N 0.000 claims 1
• TYXCXAZJXKGUQS-UHFFFAOYSA-N 2-fluoro-3-[4-[2-(5-methyl-1,2,4-oxadiazol-3-yl)morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound O1C(C)=NC(C2OCCN(C2)C=2C=3C(C=4C(=C(C#N)C=CC=4)F)=CNC=3N=CN=2)=N1 TYXCXAZJXKGUQS-UHFFFAOYSA-N 0.000 claims 1
• ZKHFKYILMCNJCH-UHFFFAOYSA-N 2-fluoro-3-[4-[2-(methoxymethyl)morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1COC(COC)CN1C1=NC=NC2=C1C(C=1C(=C(C#N)C=CC=1)F)=CN2 ZKHFKYILMCNJCH-UHFFFAOYSA-N 0.000 claims 1
• BHTWDJBVZQBRKP-UHFFFAOYSA-N 3-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 BHTWDJBVZQBRKP-UHFFFAOYSA-N 0.000 claims 1
• ZAYWYRLGHFAOON-UHFFFAOYSA-N 3-(6-methyl-4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound C=12C(C=3C=C(C=CC=3)C#N)=C(C)NC2=NC=NC=1N1CCOCC1 ZAYWYRLGHFAOON-UHFFFAOYSA-N 0.000 claims 1
• VLEUCSFUIAUHLA-UHFFFAOYSA-N 3-[4-(4,4-difluoropiperidin-1-yl)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-2-fluorobenzonitrile Chemical compound FC1=C(C#N)C=CC=C1C1=CNC2=NC=NC(N3CCC(F)(F)CC3)=C12 VLEUCSFUIAUHLA-UHFFFAOYSA-N 0.000 claims 1
• ILZPYTXOIXLWFM-UHFFFAOYSA-N 4-(4-fluoropiperidin-1-yl)-5-(2-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound COC1=CC=CC=C1C1=CNC2=NC=NC(N3CCC(F)CC3)=C12 ILZPYTXOIXLWFM-UHFFFAOYSA-N 0.000 claims 1
• NTJLGQBTTOSVMD-UHFFFAOYSA-N 4-(azetidin-1-yl)-5-(5-fluoro-2-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound COC1=CC=C(F)C=C1C1=CNC2=NC=NC(N3CCC3)=C12 NTJLGQBTTOSVMD-UHFFFAOYSA-N 0.000 claims 1
• RGWYNOKIZOFIMS-UHFFFAOYSA-N 4-[5-(1,3-dimethylpyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound CC1=NN(C)C=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 RGWYNOKIZOFIMS-UHFFFAOYSA-N 0.000 claims 1
• ICEVOSIVNSAQIF-UHFFFAOYSA-N 4-[5-(1-ethylpyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1=NN(CC)C=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 ICEVOSIVNSAQIF-UHFFFAOYSA-N 0.000 claims 1
• VNWKCLDQBNSJJO-UHFFFAOYSA-N 4-[5-(1-methylpyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1=NN(C)C=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 VNWKCLDQBNSJJO-UHFFFAOYSA-N 0.000 claims 1
• ZQFMADILMOIBBC-UHFFFAOYSA-N 4-[5-(2,6-difluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound FC1=CC=CC(F)=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 ZQFMADILMOIBBC-UHFFFAOYSA-N 0.000 claims 1
• UGVUXLJRIDUDEE-UHFFFAOYSA-N 4-[5-(2-fluoro-6-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CC=CC(F)=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 UGVUXLJRIDUDEE-UHFFFAOYSA-N 0.000 claims 1
• KISKHUBNHHURGR-UHFFFAOYSA-N 4-[5-(3-methyl-1,2-thiazol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound S1N=C(C)C=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 KISKHUBNHHURGR-UHFFFAOYSA-N 0.000 claims 1
• HGQLMWSXVBEIIO-UHFFFAOYSA-N 4-[5-(4-methoxypyridin-3-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CC=NC=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 HGQLMWSXVBEIIO-UHFFFAOYSA-N 0.000 claims 1
• QHRIVPDHKSYQOS-UHFFFAOYSA-N 4-[5-(4-methyl-1,3-thiazol-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound CC1=CSC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=N1 QHRIVPDHKSYQOS-UHFFFAOYSA-N 0.000 claims 1
• MRUMVMHGGHIFEY-UHFFFAOYSA-N 4-[5-(4-methylpyridin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound CC1=CC=NC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 MRUMVMHGGHIFEY-UHFFFAOYSA-N 0.000 claims 1
• MASZEHUSSZSJSB-UHFFFAOYSA-N 4-[5-(5-chloropyridin-3-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound ClC1=CN=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 MASZEHUSSZSJSB-UHFFFAOYSA-N 0.000 claims 1
• QPWYSUWXPGZSOH-UHFFFAOYSA-N 4-[5-(5-methylpyridin-3-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound CC1=CN=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 QPWYSUWXPGZSOH-UHFFFAOYSA-N 0.000 claims 1
• KUQRUOBHXPBUPN-UHFFFAOYSA-N 4-[5-(6-methoxypyrazin-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CN=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=N1 KUQRUOBHXPBUPN-UHFFFAOYSA-N 0.000 claims 1
• MMXALXCYCNOIET-UHFFFAOYSA-N 5-(2-methoxyphenyl)-4-pyrrolidin-1-yl-7h-pyrrolo[2,3-d]pyrimidine Chemical compound COC1=CC=CC=C1C1=CNC2=NC=NC(N3CCCC3)=C12 MMXALXCYCNOIET-UHFFFAOYSA-N 0.000 claims 1
• PYYFMDJYNIMQLA-UHFFFAOYSA-N 5-(3-fluoro-5-methoxyphenyl)-4-(4-fluoropiperidin-1-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound COC1=CC(F)=CC(C=2C3=C(N4CCC(F)CC4)N=CN=C3NC=2)=C1 PYYFMDJYNIMQLA-UHFFFAOYSA-N 0.000 claims 1
• YABCYQHQVZEFNM-UHFFFAOYSA-N 5-(3-fluorophenyl)-4-pyrrolidin-1-yl-7h-pyrrolo[2,3-d]pyrimidine Chemical compound FC1=CC=CC(C=2C3=C(N4CCCC4)N=CN=C3NC=2)=C1 YABCYQHQVZEFNM-UHFFFAOYSA-N 0.000 claims 1
• HWFMTSYUBSDCPK-UHFFFAOYSA-N 5-(5-fluoro-2-methoxyphenyl)-4-(3-fluoropiperidin-1-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound COC1=CC=C(F)C=C1C1=CNC2=NC=NC(N3CC(F)CCC3)=C12 HWFMTSYUBSDCPK-UHFFFAOYSA-N 0.000 claims 1
• CNKMORSUWBKGDA-UHFFFAOYSA-N 5-(5-fluoro-2-methoxyphenyl)-4-(4-fluoropiperidin-1-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound COC1=CC=C(F)C=C1C1=CNC2=NC=NC(N3CCC(F)CC3)=C12 CNKMORSUWBKGDA-UHFFFAOYSA-N 0.000 claims 1
• YISDXRANPXBQIV-UHFFFAOYSA-N 6-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)pyridine-2-carbonitrile Chemical compound N#CC1=CC=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=N1 YISDXRANPXBQIV-UHFFFAOYSA-N 0.000 claims 1
• CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims 1
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 1
• 201000010099 disease Diseases 0.000 abstract description 11
• 208000011231 Crohn disease Diseases 0.000 abstract description 10
• 208000015122 neurodegenerative disease Diseases 0.000 abstract description 8
• 206010028980 Neoplasm Diseases 0.000 abstract description 7
• 208000024827 Alzheimer disease Diseases 0.000 abstract description 6
• 201000011510 cancer Diseases 0.000 abstract description 5
• 206010024229 Leprosy Diseases 0.000 abstract description 4
• 230000004770 neurodegeneration Effects 0.000 abstract description 4
• 102000009784 Leucine-Rich Repeat Serine-Threonine Protein Kinase-2 Human genes 0.000 abstract 1
• 108010020246 Leucine-Rich Repeat Serine-Threonine Protein Kinase-2 Proteins 0.000 abstract 1
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