KR20150027267A - LRRK2 억제제로서의 4-(치환된-아미노)-7H-피롤로[2,3-d]피리미딘 - Google Patents
LRRK2 억제제로서의 4-(치환된-아미노)-7H-피롤로[2,3-d]피리미딘 Download PDFInfo
- Publication number
- KR20150027267A KR20150027267A KR20157002334A KR20157002334A KR20150027267A KR 20150027267 A KR20150027267 A KR 20150027267A KR 20157002334 A KR20157002334 A KR 20157002334A KR 20157002334 A KR20157002334 A KR 20157002334A KR 20150027267 A KR20150027267 A KR 20150027267A
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- KR
- South Korea
- Prior art keywords
- pyrrolo
- pyrimidin
- morpholin
- benzonitrile
- pyrimidine
- 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.)
- Ceased
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- 229940124786 LRRK2 inhibitor Drugs 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 204
- 150000003839 salts Chemical class 0.000 claims abstract description 74
- 208000018737 Parkinson disease Diseases 0.000 claims abstract description 26
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 150
- -1 hydroxy, methyl Chemical group 0.000 claims description 145
- 238000000034 method Methods 0.000 claims description 82
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 49
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 49
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 45
- 229910052757 nitrogen Inorganic materials 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 125000005842 heteroatom Chemical group 0.000 claims description 35
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 33
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 19
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 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 description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 7
- XDKNFILIFBZPKD-UHFFFAOYSA-N 4-[5-(3,4-dihydro-2h-pyran-5-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1CCOC=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 XDKNFILIFBZPKD-UHFFFAOYSA-N 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Chemical group 0.000 claims description 7
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
- 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 description 6
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 102100022404 E3 ubiquitin-protein ligase Midline-1 Human genes 0.000 claims description 6
- 101710102210 E3 ubiquitin-protein ligase Midline-1 Proteins 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- PFFIEMXZEROLOA-LBPRGKRZSA-N 3-[4-[(2s)-2-methylmorpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1CO[C@@H](C)CN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 PFFIEMXZEROLOA-LBPRGKRZSA-N 0.000 claims description 5
- ONPUDLCOMXVDQL-UHFFFAOYSA-N 3-[6-(difluoromethyl)-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(F)F)NC2=NC=NC=1N1CCOCC1 ONPUDLCOMXVDQL-UHFFFAOYSA-N 0.000 claims description 5
- 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 description 5
- FALGNGIGJAIJGO-UHFFFAOYSA-N [3-[4-(dimethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]phenyl]methanol Chemical compound C1=2C(N(C)C)=NC=NC=2NC=C1C1=CC=CC(CO)=C1 FALGNGIGJAIJGO-UHFFFAOYSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- XTVZGNYXKQQSKT-UHFFFAOYSA-N 1-[5-(1-methylpyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]piperidin-3-ol Chemical compound C1=NN(C)C=C1C1=CNC2=NC=NC(N3CC(O)CCC3)=C12 XTVZGNYXKQQSKT-UHFFFAOYSA-N 0.000 claims description 4
- YIDVVQGSCVWPGO-UHFFFAOYSA-N 2-fluoro-3-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound FC1=C(C#N)C=CC=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 YIDVVQGSCVWPGO-UHFFFAOYSA-N 0.000 claims description 4
- WTEXXJFJXIFNLJ-NSHDSACASA-N 2-fluoro-3-[4-[(2s)-2-methylmorpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1CO[C@@H](C)CN1C1=NC=NC2=C1C(C=1C(=C(C#N)C=CC=1)F)=CN2 WTEXXJFJXIFNLJ-NSHDSACASA-N 0.000 claims description 4
- XTIGQBGLUHGYQF-UHFFFAOYSA-N 3-(2-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)=CNC2=NC(C)=NC=1N1CCOCC1 XTIGQBGLUHGYQF-UHFFFAOYSA-N 0.000 claims description 4
- JZYGFRYCZUEFLK-UHFFFAOYSA-N 3-(4-piperidin-1-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2C3=C(N4CCCCC4)N=CN=C3NC=2)=C1 JZYGFRYCZUEFLK-UHFFFAOYSA-N 0.000 claims description 4
- SAOVTENLRUIQAM-UHFFFAOYSA-N 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=CC=4)C#N)=CNC=3N=CN=2)=N1 SAOVTENLRUIQAM-UHFFFAOYSA-N 0.000 claims description 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
- XJYBPVJUBUUJKF-UHFFFAOYSA-N 4-[5-(1h-pyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1COCCN1C1=NC=NC2=C1C(C1=CNN=C1)=CN2 XJYBPVJUBUUJKF-UHFFFAOYSA-N 0.000 claims description 4
- IGWCOHZVLMWAFD-UHFFFAOYSA-N 4-[5-(2,3-difluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound FC1=CC=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1F IGWCOHZVLMWAFD-UHFFFAOYSA-N 0.000 claims description 4
- ZWDUUSQSMVRZHV-UHFFFAOYSA-N 4-[5-(2-fluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound FC1=CC=CC=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 ZWDUUSQSMVRZHV-UHFFFAOYSA-N 0.000 claims description 4
- QLEJWVRFNQGYNT-UHFFFAOYSA-N 4-[5-(3,6-dihydro-2h-pyran-5-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1OCCC=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 QLEJWVRFNQGYNT-UHFFFAOYSA-N 0.000 claims description 4
- AXVWXYOCYXZGCZ-UHFFFAOYSA-N 4-[5-(3-fluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound FC1=CC=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 AXVWXYOCYXZGCZ-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- JWNOQCCPFZXUTN-UHFFFAOYSA-N 4-[5-(5-chloro-2-fluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound FC1=CC=C(Cl)C=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 JWNOQCCPFZXUTN-UHFFFAOYSA-N 0.000 claims description 4
- BDANSBILGUASKD-UHFFFAOYSA-N 4-[5-(5-fluoro-2-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CC=C(F)C=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 BDANSBILGUASKD-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- JMOMEVFJRJVJNY-ZDUSSCGKSA-N [3-[4-[(3s)-3-methylpiperidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]phenyl]methanol Chemical compound C1[C@@H](C)CCCN1C1=NC=NC2=C1C(C=1C=C(CO)C=CC=1)=CN2 JMOMEVFJRJVJNY-ZDUSSCGKSA-N 0.000 claims description 4
- QYEXQVOFWXSVBI-UHFFFAOYSA-N 3-[4-[2-(1h-pyrazol-5-yl)morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2C3=C(N4CC(OCC4)C4=NNC=C4)N=CN=C3NC=2)=C1 QYEXQVOFWXSVBI-UHFFFAOYSA-N 0.000 claims description 3
- INGQNVFEYJPJFN-UHFFFAOYSA-N 3-[4-[2-(3-methyl-1,2-oxazol-5-yl)morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound O1N=C(C)C=C1C1OCCN(C=2C=3C(C=4C=C(C=CC=4)C#N)=CNC=3N=CN=2)C1 INGQNVFEYJPJFN-UHFFFAOYSA-N 0.000 claims description 3
- MMCZXHZCSBHBOJ-UHFFFAOYSA-N 4-[5-[3-(1,2,4-oxadiazol-3-yl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1COCCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C1=NOC=N1)=CN2 MMCZXHZCSBHBOJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 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
- CZUHAOMXATZIIC-JTQLQIEISA-N (2s)-2-methyl-4-[5-(1-methylpyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1CO[C@@H](C)CN1C1=NC=NC2=C1C(C1=CN(C)N=C1)=CN2 CZUHAOMXATZIIC-JTQLQIEISA-N 0.000 claims description 2
- FXWRFSPVQWGHIR-LBPRGKRZSA-N (2s)-2-methyl-4-[5-(5-methylpyridin-3-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1CO[C@@H](C)CN1C1=NC=NC2=C1C(C=1C=C(C)C=NC=1)=CN2 FXWRFSPVQWGHIR-LBPRGKRZSA-N 0.000 claims description 2
- VGTLBPASJCZAFD-LBPRGKRZSA-N (2s)-4-[5-(2-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]-2-methylmorpholine Chemical compound COC1=CC=CC=C1C1=CNC2=NC=NC(N3C[C@H](C)OCC3)=C12 VGTLBPASJCZAFD-LBPRGKRZSA-N 0.000 claims description 2
- WZOCVLIZBXKCIZ-NSHDSACASA-N (2s)-4-[5-(3-fluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]-2-methylmorpholine Chemical compound C1CO[C@@H](C)CN1C1=NC=NC2=C1C(C=1C=C(F)C=CC=1)=CN2 WZOCVLIZBXKCIZ-NSHDSACASA-N 0.000 claims description 2
- ZFXOQGPDYHYOLS-NSHDSACASA-N (2s)-4-[5-(5-fluoro-2-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]-2-methylmorpholine Chemical compound COC1=CC=C(F)C=C1C1=CNC2=NC=NC(N3C[C@H](C)OCC3)=C12 ZFXOQGPDYHYOLS-NSHDSACASA-N 0.000 claims description 2
- XUDFUERXQXOOMM-UHFFFAOYSA-N 1,5-dimethyl-4-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)pyrrole-2-carbonitrile Chemical compound C1=C(C#N)N(C)C(C)=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 XUDFUERXQXOOMM-UHFFFAOYSA-N 0.000 claims description 2
- SWBMTULEVBPEDZ-UHFFFAOYSA-N 1-(5-phenyl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-3-carboxamide Chemical compound C1C(C(=O)N)CCCN1C1=NC=NC2=C1C(C=1C=CC=CC=1)=CN2 SWBMTULEVBPEDZ-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 description 2
- KJJOMGASMNZRSR-UHFFFAOYSA-N 1-[5-(3-cyanophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]piperidine-3-carbonitrile Chemical compound C1C(C#N)CCCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 KJJOMGASMNZRSR-UHFFFAOYSA-N 0.000 claims description 2
- FFFVFLJBIVJUEA-UHFFFAOYSA-N 1-[5-(3-cyanophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]piperidine-3-carboxamide Chemical compound C1C(C(=O)N)CCCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 FFFVFLJBIVJUEA-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- OAGXISWXYQYLEZ-UHFFFAOYSA-N 1-[5-[3-(hydroxymethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]piperidine-3-carbonitrile Chemical compound OCC1=CC=CC(C=2C3=C(N4CC(CCC4)C#N)N=CN=C3NC=2)=C1 OAGXISWXYQYLEZ-UHFFFAOYSA-N 0.000 claims description 2
- OZNNCYFDQWZWPW-UHFFFAOYSA-N 1-methyl-4-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)imidazole-2-carbonitrile Chemical compound N1=C(C#N)N(C)C=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 OZNNCYFDQWZWPW-UHFFFAOYSA-N 0.000 claims description 2
- IYQTYHISVSPMSU-UHFFFAOYSA-N 1-methyl-4-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)pyrrole-2-carbonitrile Chemical compound C1=C(C#N)N(C)C=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 IYQTYHISVSPMSU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- LXODCZJCWAAMGA-UHFFFAOYSA-N 2-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound N#CC1=CC=CC=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 LXODCZJCWAAMGA-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- ZRJIYGGDPFWFFW-NSHDSACASA-N 2-fluoro-3-[4-[(3s)-3-fluoropyrrolidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1[C@@H](F)CCN1C1=NC=NC2=C1C(C=1C(=C(C#N)C=CC=1)F)=CN2 ZRJIYGGDPFWFFW-NSHDSACASA-N 0.000 claims description 2
- IGANZPRDUTWWRQ-LBPRGKRZSA-N 2-fluoro-3-[4-[(3s)-3-methylpiperidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1[C@@H](C)CCCN1C1=NC=NC2=C1C(C=1C(=C(C#N)C=CC=1)F)=CN2 IGANZPRDUTWWRQ-LBPRGKRZSA-N 0.000 claims description 2
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Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261666299P | 2012-06-29 | 2012-06-29 | |
| US61/666,299 | 2012-06-29 | ||
| US201361820828P | 2013-05-08 | 2013-05-08 | |
| US61/820,828 | 2013-05-08 | ||
| PCT/IB2013/055039 WO2014001973A1 (en) | 2012-06-29 | 2013-06-19 | NOVEL 4-(SUBSTITUTED-AMINO)-7H-PYRROLO[2,3-d]PYRIMIDINES AS LRRK2 INHIBITORS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20150027267A true KR20150027267A (ko) | 2015-03-11 |
Family
ID=49029142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR20157002334A Ceased KR20150027267A (ko) | 2012-06-29 | 2013-06-19 | LRRK2 억제제로서의 4-(치환된-아미노)-7H-피롤로[2,3-d]피리미딘 |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US9156845B2 (enExample) |
| EP (2) | EP3255049A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2019221566A1 (ko) * | 2018-05-18 | 2019-11-21 | 재단법인 대구경북첨단의료산업진흥재단 | 외상성 뇌손상 또는 뇌졸중의 예방 또는 치료용 약학적 조성물 |
| WO2020040591A1 (ko) * | 2018-08-23 | 2020-02-27 | 재단법인 대구경북첨단의료산업진흥재단 | Lrrk 키나아제 저해제를 유효성분으로 함유하는 피리미딘 유도체의 신규용도 |
| WO2025170397A1 (ko) * | 2024-02-07 | 2025-08-14 | 노보렉스 주식회사 | Lrrk2 단백질 키나제 도메인 억제제로서 신규한 화합물 |
| KR20250123656A (ko) * | 2024-02-07 | 2025-08-18 | 노보렉스 주식회사 | Lrrk2 단백질 키나제 도메인 억제제로서 신규한 화합물 |
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