TWI482774B - 作爲ＬＲＲＫ２抑制劑之新穎４－（經取代胺基）－７Ｈ－吡咯并［２，３－ｄ］嘧啶類 - Google Patents

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Publication number

TWI482774B

TWI482774B TW102122705A TW102122705A TWI482774B TW I482774 B TWI482774 B TW I482774B TW 102122705 A TW102122705 A TW 102122705A TW 102122705 A TW102122705 A TW 102122705A TW I482774 B TWI482774 B TW I482774B

Authority

TW

Taiwan

Prior art keywords

pyrrolo

pyrimidin

pyrimidine

benzonitrile

methyl

Prior art date

2012-06-29

Links

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• 229940124786 LRRK2 inhibitor Drugs 0.000 title description 6
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 417
• -1 5-methyl-1,2,4-oxadiazol-3-yl Chemical group 0.000 claims description 271
• 150000001875 compounds Chemical class 0.000 claims description 205
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 196
• 229960001802 phenylephrine Drugs 0.000 claims description 113
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 82
• 150000003839 salts Chemical class 0.000 claims description 68
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 44
• 229910052757 nitrogen Inorganic materials 0.000 claims description 41
• 125000005842 heteroatom Chemical group 0.000 claims description 28
• 208000018737 Parkinson disease Diseases 0.000 claims description 27
• 229910052760 oxygen Inorganic materials 0.000 claims description 23
• 229910052717 sulfur Inorganic materials 0.000 claims description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
• 229910052739 hydrogen Inorganic materials 0.000 claims description 19
• 125000001072 heteroaryl group Chemical group 0.000 claims description 17
• 239000001257 hydrogen Substances 0.000 claims description 17
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 16
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 15
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 15
• FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims description 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 12
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 11
• 239000003814 drug Substances 0.000 claims description 10
• SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 claims description 10
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 125000005843 halogen group Chemical group 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 239000003937 drug carrier Substances 0.000 claims description 8
• KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 7
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
• 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 6
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 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 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
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 239000010200 folin Substances 0.000 claims description 4
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• JLOZHIGASXYVKY-UHFFFAOYSA-N 3-[4-(dimethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1=2C(N(C)C)=NC=NC=2NC=C1C1=CC=CC(C#N)=C1 JLOZHIGASXYVKY-UHFFFAOYSA-N 0.000 claims description 3
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=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
• 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 3
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 3
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
• 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 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• 125000001475 halogen functional group Chemical group 0.000 claims description 3
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
• BIWOSRSKDCZIFM-UHFFFAOYSA-N piperidin-3-ol Chemical compound OC1CCCNC1 BIWOSRSKDCZIFM-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
• GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-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
• 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
• 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
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 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
• 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 description 2
• WRCUUITXMHZHGJ-UHFFFAOYSA-N 3-(4-pyrrolidin-1-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2C3=C(N4CCCC4)N=CN=C3NC=2)=C1 WRCUUITXMHZHGJ-UHFFFAOYSA-N 0.000 claims description 2
• VIRVQRWTXFSQOS-UHFFFAOYSA-N 3-[4-(3,3-difluoropiperidin-1-yl)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1C(F)(F)CCCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 VIRVQRWTXFSQOS-UHFFFAOYSA-N 0.000 claims description 2
• ZIIYDYQRAOEXTB-UHFFFAOYSA-N 3-[4-(3,3-dimethylpiperidin-1-yl)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1C(C)(C)CCCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 ZIIYDYQRAOEXTB-UHFFFAOYSA-N 0.000 claims description 2
• GCHHHYMKNXQPDG-UHFFFAOYSA-N 3-[4-(3-aminopiperidin-1-yl)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1C(N)CCCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 GCHHHYMKNXQPDG-UHFFFAOYSA-N 0.000 claims description 2
• AVJKBMZZZJEKJL-UHFFFAOYSA-N 3-[4-(3-fluoropiperidin-1-yl)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1C(F)CCCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 AVJKBMZZZJEKJL-UHFFFAOYSA-N 0.000 claims description 2
• CTQLDDHACGXLAE-UHFFFAOYSA-N 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=CC=1)C#N)=CN2 CTQLDDHACGXLAE-UHFFFAOYSA-N 0.000 claims description 2
• DXUWKWSSIFZNNG-UHFFFAOYSA-N 3-[4-(4-hydroxypiperidin-1-yl)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1CC(O)CCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 DXUWKWSSIFZNNG-UHFFFAOYSA-N 0.000 claims description 2
• ZVNIBXSYPFDNBB-UHFFFAOYSA-N 3-[4-(4-oxopiperidin-1-yl)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1CC(=O)CCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 ZVNIBXSYPFDNBB-UHFFFAOYSA-N 0.000 claims description 2
• CHQSECXFXGQREC-UHFFFAOYSA-N 3-[4-(diethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1=2C(N(CC)CC)=NC=NC=2NC=C1C1=CC=CC(C#N)=C1 CHQSECXFXGQREC-UHFFFAOYSA-N 0.000 claims description 2
• HBMHDXNCFKHMQO-UHFFFAOYSA-N 3-[4-[(1-methylpiperidin-3-yl)amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1N(C)CCCC1NC1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 HBMHDXNCFKHMQO-UHFFFAOYSA-N 0.000 claims description 2
• BDJRDQDPISRMLT-ZDUSSCGKSA-N 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=CC=1)C#N)=CN2 BDJRDQDPISRMLT-ZDUSSCGKSA-N 0.000 claims description 2
• CTQLDDHACGXLAE-AWEZNQCLSA-N 3-[4-[(3s)-3-hydroxypiperidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1[C@@H](O)CCCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 CTQLDDHACGXLAE-AWEZNQCLSA-N 0.000 claims description 2
• XHHPXPWBWLLEJU-LBPRGKRZSA-N 3-[4-[(3s)-3-methylpiperidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzamide Chemical compound C1[C@@H](C)CCCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C(N)=O)=CN2 XHHPXPWBWLLEJU-LBPRGKRZSA-N 0.000 claims description 2
• WAKBGPGJEVOMFS-LBPRGKRZSA-N 3-[4-[(3s)-3-methylpiperidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzoic acid Chemical compound C1[C@@H](C)CCCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C(O)=O)=CN2 WAKBGPGJEVOMFS-LBPRGKRZSA-N 0.000 claims description 2
• JVZPSXHVFCDWFE-LBPRGKRZSA-N 3-[4-[(3s)-3-methylpiperidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]phenol Chemical compound C1[C@@H](C)CCCN1C1=NC=NC2=C1C(C=1C=C(O)C=CC=1)=CN2 JVZPSXHVFCDWFE-LBPRGKRZSA-N 0.000 claims description 2
• OKUUUFUWBALHGR-LBPRGKRZSA-N 3-[4-[(3s)-3-methylpyrrolidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1[C@@H](C)CCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 OKUUUFUWBALHGR-LBPRGKRZSA-N 0.000 claims description 2
• ORWMMNXXXMHXIQ-UHFFFAOYSA-N 3-[4-[3-(5-methyl-1,3,4-oxadiazol-2-yl)piperidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound O1C(C)=NN=C1C1CN(C=2C=3C(C=4C=C(C=CC=4)C#N)=CNC=3N=CN=2)CCC1 ORWMMNXXXMHXIQ-UHFFFAOYSA-N 0.000 claims description 2
• KGZIFOHLKHKAGT-UHFFFAOYSA-N 3-[4-[4-(1h-imidazol-2-yl)piperidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2C3=C(N4CCC(CC4)C=4NC=CN=4)N=CN=C3NC=2)=C1 KGZIFOHLKHKAGT-UHFFFAOYSA-N 0.000 claims description 2
• FUQOJXSIFZAUKX-UHFFFAOYSA-N 3-[4-[4-(1h-pyrazol-5-yl)piperidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2C3=C(N4CCC(CC4)C4=NNC=C4)N=CN=C3NC=2)=C1 FUQOJXSIFZAUKX-UHFFFAOYSA-N 0.000 claims description 2
• 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
• HZOIUUMKYGXMKG-UHFFFAOYSA-N 4-(4-fluoropiperidin-1-yl)-5-(1-methylpyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1=NN(C)C=C1C1=CNC2=NC=NC(N3CCC(F)CC3)=C12 HZOIUUMKYGXMKG-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• OJIYMEIFXMQAHK-NSHDSACASA-N 4-[(3s)-3-methylpiperidin-1-yl]-5-(1-methylpyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1[C@@H](C)CCCN1C1=NC=NC2=C1C(C1=CN(C)N=C1)=CN2 OJIYMEIFXMQAHK-NSHDSACASA-N 0.000 claims description 2
• HXQMKRWPVZHMNI-LBPRGKRZSA-N 4-[(3s)-3-methylpiperidin-1-yl]-5-(1h-pyrrolo[3,2-b]pyridin-6-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1[C@@H](C)CCCN1C1=NC=NC2=C1C(C=1C=C3NC=CC3=NC=1)=CN2 HXQMKRWPVZHMNI-LBPRGKRZSA-N 0.000 claims description 2
• LYJFMIVHZQICEH-LBPRGKRZSA-N 4-[(3s)-3-methylpiperidin-1-yl]-5-(5-methylpyridin-3-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1[C@@H](C)CCCN1C1=NC=NC2=C1C(C=1C=C(C)C=NC=1)=CN2 LYJFMIVHZQICEH-LBPRGKRZSA-N 0.000 claims description 2
• QQYKHLNTISFLOD-TXEJJXNPSA-N 4-[(3s,5r)-3,5-dimethylpiperidin-1-yl]-5-(1-methylpyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1[C@@H](C)C[C@@H](C)CN1C1=NC=NC2=C1C(C1=CN(C)N=C1)=CN2 QQYKHLNTISFLOD-TXEJJXNPSA-N 0.000 claims description 2
• KMYQVQCPFIBPJU-ZDUSSCGKSA-N 4-methoxy-3-[4-[(3s)-3-methylpiperidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound COC1=CC=C(C#N)C=C1C1=CNC2=NC=NC(N3C[C@@H](C)CCC3)=C12 KMYQVQCPFIBPJU-ZDUSSCGKSA-N 0.000 claims description 2
• WWWWAOILKADNLQ-LBPRGKRZSA-N 5-(1h-indazol-5-yl)-4-[(3s)-3-methylpiperidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1[C@@H](C)CCCN1C1=NC=NC2=C1C(C=1C=C3C=NNC3=CC=1)=CN2 WWWWAOILKADNLQ-LBPRGKRZSA-N 0.000 claims description 2
• ZIMZASTWEGEPSP-LBPRGKRZSA-N 5-(2-fluorophenyl)-4-[(3s)-3-methylpiperidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1[C@@H](C)CCCN1C1=NC=NC2=C1C(C=1C(=CC=CC=1)F)=CN2 ZIMZASTWEGEPSP-LBPRGKRZSA-N 0.000 claims description 2
• 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 description 2
• FCQGLPMXRIMRIK-UHFFFAOYSA-N 5-(2-methoxyphenyl)-n,n-dimethyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound COC1=CC=CC=C1C1=CNC2=NC=NC(N(C)C)=C12 FCQGLPMXRIMRIK-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• HEWGOSXSILHLLQ-UHFFFAOYSA-N 5-(3-fluoro-5-methoxyphenyl)-n,n-dimethyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound COC1=CC(F)=CC(C=2C3=C(N(C)C)N=CN=C3NC=2)=C1 HEWGOSXSILHLLQ-UHFFFAOYSA-N 0.000 claims description 2
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