JP6189948B2 - ＬＲＲＫ２阻害薬としての新規な４−（置換アミノ）−７Ｈ−ピロロ［２，３−ｄ］ピリミジン - Google Patents

Info

Publication number

JP6189948B2

JP6189948B2 JP2015519416A JP2015519416A JP6189948B2 JP 6189948 B2 JP6189948 B2 JP 6189948B2 JP 2015519416 A JP2015519416 A JP 2015519416A JP 2015519416 A JP2015519416 A JP 2015519416A JP 6189948 B2 JP6189948 B2 JP 6189948B2

Authority

JP

Japan

Prior art keywords

pyrrolo

morpholin

pyrimidine

pyrimidin

methyl

Prior art date

2012-06-29

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.)

Expired - Fee Related

Links

• Espacenet
• Global Dossier
• Discuss

• -1 4- (substituted amino) -7H-pyrrolo [2,3-d] pyrimidines Chemical class 0.000 title claims description 114
• 229940124786 LRRK2 inhibitor Drugs 0.000 title description 6
• 150000001875 compounds Chemical class 0.000 claims description 215
• 150000003839 salts Chemical class 0.000 claims description 68
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 47
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 35
• 229910052757 nitrogen Inorganic materials 0.000 claims description 30
• 125000005842 heteroatom Chemical group 0.000 claims description 27
• 208000018737 Parkinson disease Diseases 0.000 claims description 25
• 229910052760 oxygen Inorganic materials 0.000 claims description 22
• 229910052717 sulfur Inorganic materials 0.000 claims description 20
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims description 17
• 239000001257 hydrogen Substances 0.000 claims description 15
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
• 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 12
• 125000005843 halogen group Chemical group 0.000 claims description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• 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 10
• 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 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 10
• 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 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 239000003937 drug carrier Substances 0.000 claims description 9
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 5
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 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
• 125000001309 chloro group Chemical group Cl* 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 3
• 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 3
• 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 description 3
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
• 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 3
• 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 3
• 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 3
• 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 3
• ONFLVQULIQDDSN-UHFFFAOYSA-N 4-[5-(3-chlorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound ClC1=CC=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 ONFLVQULIQDDSN-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• WLBWMAISCIFWAN-UHFFFAOYSA-N 4-[5-(5-bromopyridin-3-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound BrC1=CN=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 WLBWMAISCIFWAN-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• CZUHAOMXATZIIC-SNVBAGLBSA-N (2r)-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-SNVBAGLBSA-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
• 125000006582 (C5-C6) heterocycloalkyl group Chemical group 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
• 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
• PFFIEMXZEROLOA-GFCCVEGCSA-N 3-[4-[(2r)-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-GFCCVEGCSA-N 0.000 claims description 2
• XRIIKVLOTOSHOP-LBPRGKRZSA-N 3-[4-[(3s)-3-methylmorpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C[C@H]1COCCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 XRIIKVLOTOSHOP-LBPRGKRZSA-N 0.000 claims description 2
• QYMXFRIVGZZMAD-UHFFFAOYSA-N 3-[4-[2-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound O1C(C)=NC(CC2OCCN(C2)C=2C=3C(C=4C=C(C=CC=4)C#N)=CNC=3N=CN=2)=N1 QYMXFRIVGZZMAD-UHFFFAOYSA-N 0.000 claims description 2
• QGBBQZOBGGTKLP-UHFFFAOYSA-N 3-chloro-5-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound ClC1=CC(C#N)=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 QGBBQZOBGGTKLP-UHFFFAOYSA-N 0.000 claims description 2
• GAMPREVSPQKZEE-UHFFFAOYSA-N 3-methoxy-5-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound COC1=CC(C#N)=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 GAMPREVSPQKZEE-UHFFFAOYSA-N 0.000 claims description 2
• FAMMXMXUDBKFET-UHFFFAOYSA-N 3-methyl-5-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound CC1=CC(C#N)=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 FAMMXMXUDBKFET-UHFFFAOYSA-N 0.000 claims description 2
• BISAHRSNHGARQL-UHFFFAOYSA-N 4-(5-imidazo[1,2-b]pyridazin-3-yl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)morpholine Chemical compound C1COCCN1C1=NC=NC2=C1C(C=1N3N=CC=CC3=NC=1)=CN2 BISAHRSNHGARQL-UHFFFAOYSA-N 0.000 claims description 2
• OCXIEZDHSFMBOX-UHFFFAOYSA-N 4-(5-isoquinolin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)morpholine Chemical compound C1COCCN1C1=NC=NC2=C1C(C=1C3=CC=CC=C3C=NC=1)=CN2 OCXIEZDHSFMBOX-UHFFFAOYSA-N 0.000 claims description 2
• MUOUHNBOXJIELS-UHFFFAOYSA-N 4-(5-phenyl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)morpholine Chemical compound C1COCCN1C1=NC=NC2=C1C(C=1C=CC=CC=1)=CN2 MUOUHNBOXJIELS-UHFFFAOYSA-N 0.000 claims description 2
• UZSUNCZXHIZLKQ-UHFFFAOYSA-N 4-(5-pyridin-3-yl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)morpholine Chemical compound C1COCCN1C1=NC=NC2=C1C(C=1C=NC=CC=1)=CN2 UZSUNCZXHIZLKQ-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• CZDNODODMNYBAC-UHFFFAOYSA-N 4-[5-(1-methylpyrazol-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound CN1C=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=N1 CZDNODODMNYBAC-UHFFFAOYSA-N 0.000 claims description 2
• WCIXCVUKGLJANE-UHFFFAOYSA-N 4-[5-(2,4-difluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound FC1=CC(F)=CC=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 WCIXCVUKGLJANE-UHFFFAOYSA-N 0.000 claims description 2
• PXYVAWXCGMFHEJ-UHFFFAOYSA-N 4-[5-(2,5-difluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound FC1=CC=C(F)C(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 PXYVAWXCGMFHEJ-UHFFFAOYSA-N 0.000 claims description 2
• 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 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
• QSEOKDHHFXGCDV-UHFFFAOYSA-N 4-[5-(2-chloro-5-methylphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound CC1=CC=C(Cl)C(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 QSEOKDHHFXGCDV-UHFFFAOYSA-N 0.000 claims description 2
• VAMWIRPKQLTAMA-UHFFFAOYSA-N 4-[5-(2-chlorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound ClC1=CC=CC=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 VAMWIRPKQLTAMA-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• OICKVPGRZUWXPB-UHFFFAOYSA-N 4-[5-(2-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CC=CC=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 OICKVPGRZUWXPB-UHFFFAOYSA-N 0.000 claims description 2
• KIEKMNYAWLEJNU-UHFFFAOYSA-N 4-[5-(3,5-difluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound FC1=CC(F)=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 KIEKMNYAWLEJNU-UHFFFAOYSA-N 0.000 claims description 2
• LZEFYMNXDMEWJB-UHFFFAOYSA-N 4-[5-(3-fluoro-5-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CC(F)=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 LZEFYMNXDMEWJB-UHFFFAOYSA-N 0.000 claims description 2
• FGDZZZPJSRHPSU-UHFFFAOYSA-N 4-[5-(3-fluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]-2-(5-methyl-1,2,4-oxadiazol-3-yl)morpholine Chemical compound O1C(C)=NC(C2OCCN(C2)C=2C=3C(C=4C=C(F)C=CC=4)=CNC=3N=CN=2)=N1 FGDZZZPJSRHPSU-UHFFFAOYSA-N 0.000 claims description 2
• QZZMUIJVVAGHJA-UHFFFAOYSA-N 4-[5-(3-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CC=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 QZZMUIJVVAGHJA-UHFFFAOYSA-N 0.000 claims description 2
• JMAPTHRNJHOVDP-UHFFFAOYSA-N 4-[5-(3-methylphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound CC1=CC=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 JMAPTHRNJHOVDP-UHFFFAOYSA-N 0.000 claims description 2
• YSHZFIKJKZMGKM-UHFFFAOYSA-N 4-[5-(3-methylsulfanylphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound CSC1=CC=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 YSHZFIKJKZMGKM-UHFFFAOYSA-N 0.000 claims description 2
• TZWUTAYHWCWNFP-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1=CC(F)=CC=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 TZWUTAYHWCWNFP-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• RDWJLLROTWAZQP-UHFFFAOYSA-N 4-[5-(5-chloro-2-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CC=C(Cl)C=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 RDWJLLROTWAZQP-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• BGKRVFNWCIAJLP-UHFFFAOYSA-N 4-[5-(5-fluoro-2-methylphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound CC1=CC=C(F)C=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 BGKRVFNWCIAJLP-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• UNUXAPUQXDNFJP-UHFFFAOYSA-N 4-fluoro-3-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound FC1=CC=C(C#N)C=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 UNUXAPUQXDNFJP-UHFFFAOYSA-N 0.000 claims description 2
• WMQMVSJGFSPNGK-UHFFFAOYSA-N 4-methoxy-3-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound COC1=CC=C(C#N)C=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 WMQMVSJGFSPNGK-UHFFFAOYSA-N 0.000 claims description 2
• AKFLJDSVSOFZFA-UHFFFAOYSA-N [2-fluoro-3-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl]methanol Chemical compound OCC1=CC=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1F AKFLJDSVSOFZFA-UHFFFAOYSA-N 0.000 claims description 2
• BZLDSVLRJULHNF-UHFFFAOYSA-N [2-fluoro-5-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl]methanol Chemical compound C1=C(F)C(CO)=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 BZLDSVLRJULHNF-UHFFFAOYSA-N 0.000 claims description 2
• WSFKANMHWWIKSD-UHFFFAOYSA-N [3-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl]methanol Chemical compound OCC1=CC=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 WSFKANMHWWIKSD-UHFFFAOYSA-N 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 120
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 87
• 239000000047 product Substances 0.000 description 76
• 239000000243 solution Substances 0.000 description 72
• 238000003786 synthesis reaction Methods 0.000 description 64
• 230000015572 biosynthetic process Effects 0.000 description 63
• 238000000034 method Methods 0.000 description 63
• 239000011541 reaction mixture Substances 0.000 description 62
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 54
• 239000000203 mixture Substances 0.000 description 52
• 239000007787 solid Substances 0.000 description 47
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
• 101000941879 Homo sapiens Leucine-rich repeat serine/threonine-protein kinase 2 Proteins 0.000 description 45
• 102100032693 Leucine-rich repeat serine/threonine-protein kinase 2 Human genes 0.000 description 45
• 238000005481 NMR spectroscopy Methods 0.000 description 45
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 39
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 37
• 239000002904 solvent Substances 0.000 description 35
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 34
• 238000006243 chemical reaction Methods 0.000 description 32
• 229920006395 saturated elastomer Polymers 0.000 description 28
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
• 238000000746 purification Methods 0.000 description 27
• 239000003921 oil Substances 0.000 description 24
• 239000003208 petroleum Substances 0.000 description 23
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 22
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 22
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 22
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
• 229910052799 carbon Inorganic materials 0.000 description 20
• 238000002360 preparation method Methods 0.000 description 20
• 229910052938 sodium sulfate Inorganic materials 0.000 description 20
• 235000011152 sodium sulphate Nutrition 0.000 description 20
• 239000012044 organic layer Substances 0.000 description 19
• 239000011780 sodium chloride Substances 0.000 description 19
• XXGYVFAKVLKYMQ-UHFFFAOYSA-N 2-[(4-chloro-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)methoxy]ethyl-trimethylsilane Chemical compound N1=CN=C2N(COCC[Si](C)(C)C)C=C(I)C2=C1Cl XXGYVFAKVLKYMQ-UHFFFAOYSA-N 0.000 description 18
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 18
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 18
• 125000001424 substituent group Chemical group 0.000 description 18
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
• 238000002953 preparative HPLC Methods 0.000 description 15
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
• 239000003112 inhibitor Substances 0.000 description 14
• 150000001721 carbon Chemical group 0.000 description 13
• 208000035475 disorder Diseases 0.000 description 13
• 239000003480 eluent Substances 0.000 description 13
• IATWZUFIKKEFOI-UHFFFAOYSA-N 3-(4-chloro-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound C1=2C(Cl)=NC=NC=2NC=C1C1=CC=CC(C#N)=C1 IATWZUFIKKEFOI-UHFFFAOYSA-N 0.000 description 12
• 208000024827 Alzheimer disease Diseases 0.000 description 12
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 12
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 229910052796 boron Inorganic materials 0.000 description 12
• 238000004587 chromatography analysis Methods 0.000 description 12
• 239000000741 silica gel Substances 0.000 description 12
• 229910002027 silica gel Inorganic materials 0.000 description 12
• DEDJDGOXYKQVAP-UHFFFAOYSA-N 2-[(5-iodo-4-morpholin-4-ylpyrrolo[2,3-d]pyrimidin-7-yl)methoxy]ethyl-trimethylsilane Chemical compound N1=CN=C2N(COCC[Si](C)(C)C)C=C(I)C2=C1N1CCOCC1 DEDJDGOXYKQVAP-UHFFFAOYSA-N 0.000 description 11
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 11
• 230000000694 effects Effects 0.000 description 11
• 235000019253 formic acid Nutrition 0.000 description 11
• 229910000027 potassium carbonate Inorganic materials 0.000 description 11
• 125000006413 ring segment Chemical group 0.000 description 11
• 238000010898 silica gel chromatography Methods 0.000 description 11
• 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 10
• 241000124008 Mammalia Species 0.000 description 10
• 239000002585 base Substances 0.000 description 10
• 239000003814 drug Substances 0.000 description 10
• 125000000592 heterocycloalkyl group Chemical group 0.000 description 10
• 230000035772 mutation Effects 0.000 description 10
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 9
• 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 description 9
• 125000004429 atom Chemical group 0.000 description 9
• 201000010099 disease Diseases 0.000 description 9
• 239000002552 dosage form Substances 0.000 description 9
• 238000009472 formulation Methods 0.000 description 9
• 239000000651 prodrug Substances 0.000 description 9
• 229940002612 prodrug Drugs 0.000 description 9
• 208000020016 psychiatric disease Diseases 0.000 description 9
• 208000011231 Crohn disease Diseases 0.000 description 8
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
• 238000006069 Suzuki reaction reaction Methods 0.000 description 8
• 125000004432 carbon atom Chemical group C* 0.000 description 8
• 125000000753 cycloalkyl group Chemical group 0.000 description 8
• 125000001072 heteroaryl group Chemical group 0.000 description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
• 230000005764 inhibitory process Effects 0.000 description 8
• 239000000126 substance Substances 0.000 description 8
• 239000000758 substrate Substances 0.000 description 8
• 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 description 7
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
• 208000012902 Nervous system disease Diseases 0.000 description 7
• 208000025966 Neurological disease Diseases 0.000 description 7
• 239000002253 acid Substances 0.000 description 7
• 239000013543 active substance Substances 0.000 description 7
• 239000003795 chemical substances by application Substances 0.000 description 7
• 208000015122 neurodegenerative disease Diseases 0.000 description 7
• 125000006239 protecting group Chemical group 0.000 description 7
• 230000035484 reaction time Effects 0.000 description 7
• 238000010992 reflux Methods 0.000 description 7
• 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 description 6
• 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 description 6
• 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 description 6
• 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 description 6
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
• 102000006378 Catechol O-methyltransferase Human genes 0.000 description 6
• 108020002739 Catechol O-methyltransferase Proteins 0.000 description 6
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
• 108091000080 Phosphotransferase Proteins 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 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 description 6
• 229910021529 ammonia Inorganic materials 0.000 description 6
• 125000003118 aryl group Chemical group 0.000 description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
• 229940079593 drug Drugs 0.000 description 6
• 239000001301 oxygen Substances 0.000 description 6
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
• 102000020233 phosphotransferase Human genes 0.000 description 6
• 230000002829 reductive effect Effects 0.000 description 6
• 229940076279 serotonin Drugs 0.000 description 6
• 239000003826 tablet Substances 0.000 description 6
• AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 6
• FVMRAGGGAKJPDX-AWEZNQCLSA-N 2-[[5-iodo-4-[(3s)-3-methylpiperidin-1-yl]pyrrolo[2,3-d]pyrimidin-7-yl]methoxy]ethyl-trimethylsilane Chemical compound C1[C@@H](C)CCCN1C1=NC=NC2=C1C(I)=CN2COCC[Si](C)(C)C FVMRAGGGAKJPDX-AWEZNQCLSA-N 0.000 description 5
• 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 description 5
• JVHTUXUZMDJHIR-UHFFFAOYSA-N 4-chloro-5-(1-methylpyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1=NN(C)C=C1C1=CNC2=NC=NC(Cl)=C12 JVHTUXUZMDJHIR-UHFFFAOYSA-N 0.000 description 5
• HUYFCWFTAOFDQD-UHFFFAOYSA-N 5-bromo-4-chloro-7-(4-methylphenyl)sulfonylpyrrolo[2,3-d]pyrimidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=NC=NC(Cl)=C2C(Br)=C1 HUYFCWFTAOFDQD-UHFFFAOYSA-N 0.000 description 5
• TXAZMYBMOFJBSQ-AWEZNQCLSA-N 5-bromo-7-(4-methylphenyl)sulfonyl-4-[(3s)-3-methylpiperidin-1-yl]pyrrolo[2,3-d]pyrimidine Chemical compound C1[C@@H](C)CCCN1C1=NC=NC2=C1C(Br)=CN2S(=O)(=O)C1=CC=C(C)C=C1 TXAZMYBMOFJBSQ-AWEZNQCLSA-N 0.000 description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
• HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 5
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
• 239000007864 aqueous solution Substances 0.000 description 5
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 5
• 229910000024 caesium carbonate Inorganic materials 0.000 description 5
• 239000003054 catalyst Substances 0.000 description 5
• 239000003153 chemical reaction reagent Substances 0.000 description 5
• 125000004122 cyclic group Chemical group 0.000 description 5
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 5
• QNXXNOAXMRJFPK-UHFFFAOYSA-N formic acid 4-[5-(1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound OC=O.C1CN(CCO1)c1ncnc2[nH]cc(-c3cn[nH]c3)c12 QNXXNOAXMRJFPK-UHFFFAOYSA-N 0.000 description 5
• 239000000543 intermediate Substances 0.000 description 5
• 239000010410 layer Substances 0.000 description 5
• 150000007524 organic acids Chemical class 0.000 description 5
• 235000005985 organic acids Nutrition 0.000 description 5
• 238000012746 preparative thin layer chromatography Methods 0.000 description 5
• 229940044551 receptor antagonist Drugs 0.000 description 5
• 239000002464 receptor antagonist Substances 0.000 description 5
• 238000004007 reversed phase HPLC Methods 0.000 description 5
• 102200092160 rs34637584 Human genes 0.000 description 5
• 239000007921 spray Substances 0.000 description 5
• 239000011593 sulfur Substances 0.000 description 5
• 239000000725 suspension Substances 0.000 description 5
• 208000024891 symptom Diseases 0.000 description 5
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
• CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 4
• YYSLAWXDXHVRHU-UHFFFAOYSA-N 1-(oxan-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CN(C2OCCCC2)N=C1 YYSLAWXDXHVRHU-UHFFFAOYSA-N 0.000 description 4
• IEPMBXMCDYITET-UHFFFAOYSA-N 2-(3-methyl-1,2-oxazol-5-yl)morpholine Chemical compound O1N=C(C)C=C1C1OCCNC1 IEPMBXMCDYITET-UHFFFAOYSA-N 0.000 description 4
• HWKSQZFJUUYAMP-UHFFFAOYSA-N 2-[(4-chloro-5-iodo-6-methylpyrrolo[2,3-d]pyrimidin-7-yl)methoxy]ethyl-trimethylsilane Chemical compound N1=CN=C2N(COCC[Si](C)(C)C)C(C)=C(I)C2=C1Cl HWKSQZFJUUYAMP-UHFFFAOYSA-N 0.000 description 4
• IRCWCVKNJVCQJS-UHFFFAOYSA-N 2-[(5-iodo-2-methyl-4-morpholin-4-ylpyrrolo[2,3-d]pyrimidin-7-yl)methoxy]ethyl-trimethylsilane Chemical compound C=12C(I)=CN(COCC[Si](C)(C)C)C2=NC(C)=NC=1N1CCOCC1 IRCWCVKNJVCQJS-UHFFFAOYSA-N 0.000 description 4
• DLEUEHVWRALCEO-UHFFFAOYSA-N 2-[[4-chloro-5-(1-methylpyrazol-4-yl)pyrrolo[2,3-d]pyrimidin-7-yl]methoxy]ethyl-trimethylsilane Chemical compound C1=NN(C)C=C1C1=CN(COCC[Si](C)(C)C)C2=NC=NC(Cl)=C12 DLEUEHVWRALCEO-UHFFFAOYSA-N 0.000 description 4
• LXXVQQJWZBIICY-UHFFFAOYSA-N 3-(4-chloro-7h-pyrrolo[2,3-d]pyrimidin-5-yl)oxan-3-ol Chemical compound C=1NC2=NC=NC(Cl)=C2C=1C1(O)CCCOC1 LXXVQQJWZBIICY-UHFFFAOYSA-N 0.000 description 4
• ORFVTYVOAVAUBV-UHFFFAOYSA-N 3-[4-chloro-6-methyl-7-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C12=C(Cl)N=CN=C2N(COCC[Si](C)(C)C)C(C)=C1C1=CC=CC(C#N)=C1 ORFVTYVOAVAUBV-UHFFFAOYSA-N 0.000 description 4
• ZYKWKRXHROCPTA-UHFFFAOYSA-N 3-[7-(hydroxymethyl)-6-methyl-4-morpholin-4-ylpyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C12=C(N3CCOCC3)N=CN=C2N(CO)C(C)=C1C1=CC=CC(C#N)=C1 ZYKWKRXHROCPTA-UHFFFAOYSA-N 0.000 description 4
• 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 description 4
• LLTRAEBZNNXPBC-UHFFFAOYSA-N 4-benzyl-2-(3-methyl-1,2-oxazol-5-yl)morpholine Chemical compound O1N=C(C)C=C1C1OCCN(CC=2C=CC=CC=2)C1 LLTRAEBZNNXPBC-UHFFFAOYSA-N 0.000 description 4
• PLKRSMDMXVKCAM-UHFFFAOYSA-N 4-chloro-5-iodo-2-methyl-7h-pyrrolo[2,3-d]pyrimidine Chemical compound CC1=NC(Cl)=C2C(I)=CNC2=N1 PLKRSMDMXVKCAM-UHFFFAOYSA-N 0.000 description 4
• RSSKPRIVOUJMKM-UHFFFAOYSA-N 4-chloro-5-iodo-7-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-d]pyrimidine-6-carbaldehyde Chemical compound N1=CN=C2N(COCC[Si](C)(C)C)C(C=O)=C(I)C2=C1Cl RSSKPRIVOUJMKM-UHFFFAOYSA-N 0.000 description 4
• VOIAXWPHJWJDNJ-UHFFFAOYSA-N 5-iodo-4-morpholin-4-yl-7-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-d]pyrimidine-6-carbaldehyde Chemical compound N1=CN=C2N(COCC[Si](C)(C)C)C(C=O)=C(I)C2=C1N1CCOCC1 VOIAXWPHJWJDNJ-UHFFFAOYSA-N 0.000 description 4
• GPEYZJOCRPGGLW-UHFFFAOYSA-N 6-[7-(hydroxymethyl)-4-morpholin-4-ylpyrrolo[2,3-d]pyrimidin-5-yl]pyridine-2-carbonitrile Chemical compound C12=C(N3CCOCC3)N=CN=C2N(CO)C=C1C1=CC=CC(C#N)=N1 GPEYZJOCRPGGLW-UHFFFAOYSA-N 0.000 description 4
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
• 102000010111 Ezrin/radixin/moesin Human genes 0.000 description 4
• 108050001788 Ezrin/radixin/moesin Proteins 0.000 description 4
• 208000022559 Inflammatory bowel disease Diseases 0.000 description 4
• UEQUQVLFIPOEMF-UHFFFAOYSA-N Mianserin Chemical compound C1C2=CC=CC=C2N2CCN(C)CC2C2=CC=CC=C21 UEQUQVLFIPOEMF-UHFFFAOYSA-N 0.000 description 4
• 102000010909 Monoamine Oxidase Human genes 0.000 description 4
• 108010062431 Monoamine oxidase Proteins 0.000 description 4
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
• LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 4
• 206010028980 Neoplasm Diseases 0.000 description 4
• YNHIGQDRGKUECZ-UHFFFAOYSA-L PdCl2(PPh3)2 Substances [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 4
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 4
• 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 4
• CFMUBXRVBJVJIO-UHFFFAOYSA-N [3-[4-(dimethylamino)-7-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-d]pyrimidin-5-yl]phenyl]methanol Chemical compound C1=2C(N(C)C)=NC=NC=2N(COCC[Si](C)(C)C)C=C1C1=CC=CC(CO)=C1 CFMUBXRVBJVJIO-UHFFFAOYSA-N 0.000 description 4
• WEYNTKPJEUKUTE-UHFFFAOYSA-N [4-morpholin-4-yl-5-(1h-pyrazol-4-yl)pyrrolo[2,3-d]pyrimidin-7-yl]methanol Chemical compound C12=C(N3CCOCC3)N=CN=C2N(CO)C=C1C=1C=NNC=1 WEYNTKPJEUKUTE-UHFFFAOYSA-N 0.000 description 4
• DZBXUWSFODPGDX-UHFFFAOYSA-N [5-(1-methylpyrazol-4-yl)-4-morpholin-4-ylpyrrolo[2,3-d]pyrimidin-7-yl]methanol Chemical compound C1=NN(C)C=C1C1=CN(CO)C2=NC=NC(N3CCOCC3)=C12 DZBXUWSFODPGDX-UHFFFAOYSA-N 0.000 description 4
• 125000000217 alkyl group Chemical group 0.000 description 4
• 239000000908 ammonium hydroxide Substances 0.000 description 4
• 210000004556 brain Anatomy 0.000 description 4
• 229910052794 bromium Inorganic materials 0.000 description 4
• 208000010877 cognitive disease Diseases 0.000 description 4
• 238000010511 deprotection reaction Methods 0.000 description 4
• 235000014632 disordered eating Nutrition 0.000 description 4
• LZWLLMFYVGUUAL-UHFFFAOYSA-L ditert-butyl(cyclopenta-1,3-dien-1-yl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.CC(C)(C)P(C(C)(C)C)C1=CC=C[CH-]1.CC(C)(C)P(C(C)(C)C)C1=CC=C[CH-]1 LZWLLMFYVGUUAL-UHFFFAOYSA-L 0.000 description 4
• 206010013663 drug dependence Diseases 0.000 description 4
• 238000002474 experimental method Methods 0.000 description 4
• QORVDGQLPPAFRS-XPSHAMGMSA-N galantamine hydrobromide Chemical compound Br.O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 QORVDGQLPPAFRS-XPSHAMGMSA-N 0.000 description 4
• 238000010438 heat treatment Methods 0.000 description 4
• 230000002401 inhibitory effect Effects 0.000 description 4
• 210000004072 lung Anatomy 0.000 description 4
• 208000020816 lung neoplasm Diseases 0.000 description 4
• LDDHMLJTFXJGPI-UHFFFAOYSA-N memantine hydrochloride Chemical compound Cl.C1C(C2)CC3(C)CC1(C)CC2(N)C3 LDDHMLJTFXJGPI-UHFFFAOYSA-N 0.000 description 4
• CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 4
• 230000037361 pathway Effects 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 4
• MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 description 4
• 150000003384 small molecules Chemical class 0.000 description 4
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
• 235000017557 sodium bicarbonate Nutrition 0.000 description 4
• 229910000029 sodium carbonate Inorganic materials 0.000 description 4
• 238000003756 stirring Methods 0.000 description 4
• 238000006467 substitution reaction Methods 0.000 description 4
• APEKRESCNJNALD-UHFFFAOYSA-N trimethyl-[2-[[4-morpholin-4-yl-5-(1h-pyrazol-4-yl)pyrrolo[2,3-d]pyrimidin-7-yl]methoxy]ethyl]silane Chemical compound C12=C(N3CCOCC3)N=CN=C2N(COCC[Si](C)(C)C)C=C1C=1C=NNC=1 APEKRESCNJNALD-UHFFFAOYSA-N 0.000 description 4
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
• UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical group CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 4
• AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 3
• MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 3
• QWGGHPHJMPOSRL-UHFFFAOYSA-N 2-[(4-chloro-5-iodo-2-methylpyrrolo[2,3-d]pyrimidin-7-yl)methoxy]ethyl-trimethylsilane Chemical compound CC1=NC(Cl)=C2C(I)=CN(COCC[Si](C)(C)C)C2=N1 QWGGHPHJMPOSRL-UHFFFAOYSA-N 0.000 description 3
• UQRRQWLLOMPUSF-UHFFFAOYSA-N 2-[[4-chloro-5-[1-(oxan-2-yl)pyrazol-4-yl]pyrrolo[2,3-d]pyrimidin-7-yl]methoxy]ethyl-trimethylsilane Chemical compound C12=C(Cl)N=CN=C2N(COCC[Si](C)(C)C)C=C1C(=C1)C=NN1C1CCCCO1 UQRRQWLLOMPUSF-UHFFFAOYSA-N 0.000 description 3
• BNHGUHMMGBYCNR-UHFFFAOYSA-N 3-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)oxan-3-ol Chemical compound C=1NC2=NC=NC(N3CCOCC3)=C2C=1C1(O)CCCOC1 BNHGUHMMGBYCNR-UHFFFAOYSA-N 0.000 description 3
• SNKZJIOFVMKAOJ-UHFFFAOYSA-N 3-Aminopropanesulfonate Chemical compound NCCCS(O)(=O)=O SNKZJIOFVMKAOJ-UHFFFAOYSA-N 0.000 description 3
• OCVWQSSLXDPQBU-UHFFFAOYSA-N 3-[2-methyl-4-morpholin-4-yl-7-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C=12C(C=3C=C(C=CC=3)C#N)=CN(COCC[Si](C)(C)C)C2=NC(C)=NC=1N1CCOCC1 OCVWQSSLXDPQBU-UHFFFAOYSA-N 0.000 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 description 3
• FMHJQSUFZKEPTQ-UHFFFAOYSA-N 3-[6-methyl-4-morpholin-4-yl-7-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C12=C(N3CCOCC3)N=CN=C2N(COCC[Si](C)(C)C)C(C)=C1C1=CC=CC(C#N)=C1 FMHJQSUFZKEPTQ-UHFFFAOYSA-N 0.000 description 3
• IDPYRTCOKCLNHC-UHFFFAOYSA-N 5-iodo-n,n-dimethyl-7-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound CN(C)C1=NC=NC2=C1C(I)=CN2COCC[Si](C)(C)C IDPYRTCOKCLNHC-UHFFFAOYSA-N 0.000 description 3
• PMYXTHDNCFQJBG-UHFFFAOYSA-N 6-[4-morpholin-4-yl-7-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-d]pyrimidin-5-yl]pyridine-2-carbonitrile Chemical compound C12=C(N3CCOCC3)N=CN=C2N(COCC[Si](C)(C)C)C=C1C1=CC=CC(C#N)=N1 PMYXTHDNCFQJBG-UHFFFAOYSA-N 0.000 description 3
• CFOSURHAGGGJBD-UHFFFAOYSA-N 7-(4-methylphenyl)sulfonyl-4-(3-methylpiperidin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-d]pyrimidine Chemical compound C1C(C)CCCN1C1=NC=NC2=C1C(B1OC(C)(C)C(C)(C)O1)=CN2S(=O)(=O)C1=CC=C(C)C=C1 CFOSURHAGGGJBD-UHFFFAOYSA-N 0.000 description 3
• JJTNLWSCFYERCK-UHFFFAOYSA-N 7h-pyrrolo[2,3-d]pyrimidine Chemical compound N1=CN=C2NC=CC2=C1 JJTNLWSCFYERCK-UHFFFAOYSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• ODKSFYDXXFIFQN-UHFFFAOYSA-N Arginine Chemical compound OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 3
• 206010006187 Breast cancer Diseases 0.000 description 3
• 208000026310 Breast neoplasm Diseases 0.000 description 3
• JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 3
• 206010012289 Dementia Diseases 0.000 description 3
• 208000030814 Eating disease Diseases 0.000 description 3
• 208000019454 Feeding and Eating disease Diseases 0.000 description 3
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
• 102000013446 GTP Phosphohydrolases Human genes 0.000 description 3
• 241000282412 Homo Species 0.000 description 3
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
• 208000008839 Kidney Neoplasms Diseases 0.000 description 3
• WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 3
• WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 3
• 206010024229 Leprosy Diseases 0.000 description 3
• 208000019022 Mood disease Diseases 0.000 description 3
• 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 3
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 3
• 102000003729 Neprilysin Human genes 0.000 description 3
• 108090000028 Neprilysin Proteins 0.000 description 3
• DPWPWRLQFGFJFI-UHFFFAOYSA-N Pargyline Chemical compound C#CCN(C)CC1=CC=CC=C1 DPWPWRLQFGFJFI-UHFFFAOYSA-N 0.000 description 3
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• 208000000236 Prostatic Neoplasms Diseases 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• KPHSPCBQZHYDTR-UHFFFAOYSA-N [3-[4-(dimethylamino)-7-(hydroxymethyl)pyrrolo[2,3-d]pyrimidin-5-yl]phenyl]methyl 2,2,2-trifluoroacetate Chemical compound C1=2C(N(C)C)=NC=NC=2N(CO)C=C1C1=CC=CC(COC(=O)C(F)(F)F)=C1 KPHSPCBQZHYDTR-UHFFFAOYSA-N 0.000 description 3
• 239000004480 active ingredient Substances 0.000 description 3
• DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 3
• 150000001412 amines Chemical class 0.000 description 3
• KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 3
• 238000003556 assay Methods 0.000 description 3
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
• 238000009739 binding Methods 0.000 description 3
• 239000000812 cholinergic antagonist Substances 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 238000001816 cooling Methods 0.000 description 3
• 239000013078 crystal Substances 0.000 description 3
• XWAIAVWHZJNZQQ-UHFFFAOYSA-N donepezil hydrochloride Chemical compound [H+].[Cl-].O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 XWAIAVWHZJNZQQ-UHFFFAOYSA-N 0.000 description 3
• 206010015037 epilepsy Diseases 0.000 description 3
• 239000000706 filtrate Substances 0.000 description 3
• SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 3
• BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 3
• 239000000499 gel Substances 0.000 description 3
• 229910052736 halogen Inorganic materials 0.000 description 3
• 150000002367 halogens Chemical class 0.000 description 3
• 150000002431 hydrogen Chemical class 0.000 description 3
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
• CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 3
• 238000001802 infusion Methods 0.000 description 3
• 238000001990 intravenous administration Methods 0.000 description 3
• 229910052740 iodine Inorganic materials 0.000 description 3
• 210000003734 kidney Anatomy 0.000 description 3
• 229960004502 levodopa Drugs 0.000 description 3
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
• 238000004949 mass spectrometry Methods 0.000 description 3
• 150000007522 mineralic acids Chemical class 0.000 description 3
• YHXISWVBGDMDLQ-UHFFFAOYSA-N moclobemide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCCN1CCOCC1 YHXISWVBGDMDLQ-UHFFFAOYSA-N 0.000 description 3
• AUHNJVJCKGTCPI-UHFFFAOYSA-N n,n-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=2C(N(C)C)=NC=NC=2N(COCC[Si](C)(C)C)C=C1B1OC(C)(C)C(C)(C)O1 AUHNJVJCKGTCPI-UHFFFAOYSA-N 0.000 description 3
• 230000004770 neurodegeneration Effects 0.000 description 3
• 230000000626 neurodegenerative effect Effects 0.000 description 3
• 231100000252 nontoxic Toxicity 0.000 description 3
• 230000003000 nontoxic effect Effects 0.000 description 3
• 239000002674 ointment Substances 0.000 description 3
• 229910052763 palladium Inorganic materials 0.000 description 3
• 238000007911 parenteral administration Methods 0.000 description 3
• 239000000546 pharmaceutical excipient Substances 0.000 description 3
• 229920000642 polymer Polymers 0.000 description 3
• 239000000018 receptor agonist Substances 0.000 description 3
• 229940044601 receptor agonist Drugs 0.000 description 3
• 229960003946 selegiline Drugs 0.000 description 3
• 230000011664 signaling Effects 0.000 description 3
• 208000011117 substance-related disease Diseases 0.000 description 3
• 238000003419 tautomerization reaction Methods 0.000 description 3
• 238000012360 testing method Methods 0.000 description 3
• 238000004809 thin layer chromatography Methods 0.000 description 3
• MIQPIUSUKVNLNT-UHFFFAOYSA-N tolcapone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC(O)=C(O)C([N+]([O-])=O)=C1 MIQPIUSUKVNLNT-UHFFFAOYSA-N 0.000 description 3
• 238000011200 topical administration Methods 0.000 description 3
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
• RXOZSBOFDQYFRX-UHFFFAOYSA-N trimethyl-[2-[[4-morpholin-4-yl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-d]pyrimidin-7-yl]methoxy]ethyl]silane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CN(COCC[Si](C)(C)C)C2=NC=NC(N3CCOCC3)=C12 RXOZSBOFDQYFRX-UHFFFAOYSA-N 0.000 description 3
• ABYZSBXBWWOSQK-UHFFFAOYSA-N trimethyl-[2-[[4-morpholin-4-yl-5-[1-(oxan-2-yl)pyrazol-4-yl]pyrrolo[2,3-d]pyrimidin-7-yl]methoxy]ethyl]silane Chemical compound C12=C(N3CCOCC3)N=CN=C2N(COCC[Si](C)(C)C)C=C1C(=C1)C=NN1C1CCCCO1 ABYZSBXBWWOSQK-UHFFFAOYSA-N 0.000 description 3
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
• OYPPVKRFBIWMSX-SXGWCWSVSA-N zimeldine Chemical compound C=1C=CN=CC=1C(=C/CN(C)C)\C1=CC=C(Br)C=C1 OYPPVKRFBIWMSX-SXGWCWSVSA-N 0.000 description 3
• SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 2
• GJJFMKBJSRMPLA-HIFRSBDPSA-N (1R,2S)-2-(aminomethyl)-N,N-diethyl-1-phenyl-1-cyclopropanecarboxamide Chemical compound C=1C=CC=CC=1[C@@]1(C(=O)N(CC)CC)C[C@@H]1CN GJJFMKBJSRMPLA-HIFRSBDPSA-N 0.000 description 2
• XDBHWPLGGBLUHH-UHFFFAOYSA-N (3-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C#N)=C1 XDBHWPLGGBLUHH-UHFFFAOYSA-N 0.000 description 2
• ZEUITGRIYCTCEM-KRWDZBQOSA-N (S)-duloxetine Chemical compound C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)=CC=CS1 ZEUITGRIYCTCEM-KRWDZBQOSA-N 0.000 description 2
• UCNGGGYMLHAMJG-UHFFFAOYSA-N 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole Chemical compound C1=NN(C)C=C1B1OC(C)(C)C(C)(C)O1 UCNGGGYMLHAMJG-UHFFFAOYSA-N 0.000 description 2
• HHFYTUCPPVTOES-UHFFFAOYSA-N 2-[(5-iodopyrrolo[2,3-d]pyrimidin-7-yl)methoxy]ethyl-trimethylsilane Chemical compound N1=CN=C2N(COCC[Si](C)(C)C)C=C(I)C2=C1 HHFYTUCPPVTOES-UHFFFAOYSA-N 0.000 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• NNOQAGZHQSZVEV-UHFFFAOYSA-N 3-[4-chloro-7-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C12=C(Cl)N=CN=C2N(COCC[Si](C)(C)C)C=C1C1=CC=CC(C#N)=C1 NNOQAGZHQSZVEV-UHFFFAOYSA-N 0.000 description 2
• HCUDUGCVOIKARC-UHFFFAOYSA-N 3-[4-chloro-7-(hydroxymethyl)pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C12=C(Cl)N=CN=C2N(CO)C=C1C1=CC=CC(C#N)=C1 HCUDUGCVOIKARC-UHFFFAOYSA-N 0.000 description 2
• NYBATJQRPVYHQE-UHFFFAOYSA-N 3-[4-morpholin-4-yl-7-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C12=C(N3CCOCC3)N=CN=C2N(COCC[Si](C)(C)C)C=C1C1=CC=CC(C#N)=C1 NYBATJQRPVYHQE-UHFFFAOYSA-N 0.000 description 2
• RDHBVAXWJKDFSK-UHFFFAOYSA-N 3-[6-(difluoromethyl)-4-morpholin-4-yl-7-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C12=C(N3CCOCC3)N=CN=C2N(COCC[Si](C)(C)C)C(C(F)F)=C1C1=CC=CC(C#N)=C1 RDHBVAXWJKDFSK-UHFFFAOYSA-N 0.000 description 2
• UCFSYHMCKWNKAH-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OBOC1(C)C UCFSYHMCKWNKAH-UHFFFAOYSA-N 0.000 description 2
• ATIUQIBTYSVBQP-UHFFFAOYSA-N 4-benzyl-2-(3-methyl-1,2-oxazol-5-yl)morpholin-2-ol Chemical compound O1N=C(C)C=C1C1(O)OCCN(CC=2C=CC=CC=2)C1 ATIUQIBTYSVBQP-UHFFFAOYSA-N 0.000 description 2
• XKFPYPQQHFEXRZ-UHFFFAOYSA-N 5-methyl-N'-(phenylmethyl)-3-isoxazolecarbohydrazide Chemical compound O1C(C)=CC(C(=O)NNCC=2C=CC=CC=2)=N1 XKFPYPQQHFEXRZ-UHFFFAOYSA-N 0.000 description 2
• JICJBGPOMZQUBB-UHFFFAOYSA-N 7-[(3-chloro-6-methyl-5,5-dioxido-6,11-dihydrodibenzo[c,f][1,2]thiazepin-11-yl)amino]heptanoic acid Chemical compound O=S1(=O)N(C)C2=CC=CC=C2C(NCCCCCCC(O)=O)C2=CC=C(Cl)C=C21 JICJBGPOMZQUBB-UHFFFAOYSA-N 0.000 description 2
• 102000013455 Amyloid beta-Peptides Human genes 0.000 description 2
• 108010090849 Amyloid beta-Peptides Proteins 0.000 description 2
• 208000019901 Anxiety disease Diseases 0.000 description 2
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 2
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
• KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
• 208000032841 Bulimia Diseases 0.000 description 2
• 206010006550 Bulimia nervosa Diseases 0.000 description 2
• 239000004215 Carbon black (E152) Substances 0.000 description 2
• 208000005145 Cerebral amyloid angiopathy Diseases 0.000 description 2
• GDLIGKIOYRNHDA-UHFFFAOYSA-N Clomipramine Chemical compound C1CC2=CC=C(Cl)C=C2N(CCCN(C)C)C2=CC=CC=C21 GDLIGKIOYRNHDA-UHFFFAOYSA-N 0.000 description 2
• 208000028698 Cognitive impairment Diseases 0.000 description 2
• RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
• 229940081615 DOPA decarboxylase inhibitor Drugs 0.000 description 2
• HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 2
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
• XIQVNETUBQGFHX-UHFFFAOYSA-N Ditropan Chemical compound C=1C=CC=CC=1C(O)(C(=O)OCC#CCN(CC)CC)C1CCCCC1 XIQVNETUBQGFHX-UHFFFAOYSA-N 0.000 description 2
• 102000004190 Enzymes Human genes 0.000 description 2
• 108090000790 Enzymes Proteins 0.000 description 2
• YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
• KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
• 108010026288 GTP Phosphohydrolases Proteins 0.000 description 2
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical class NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
• VPNYRYCIDCJBOM-UHFFFAOYSA-M Glycopyrronium bromide Chemical compound [Br-].C1[N+](C)(C)CCC1OC(=O)C(O)(C=1C=CC=CC=1)C1CCCC1 VPNYRYCIDCJBOM-UHFFFAOYSA-M 0.000 description 2
• XKMLYUALXHKNFT-UUOKFMHZSA-N Guanosine-5'-triphosphate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XKMLYUALXHKNFT-UUOKFMHZSA-N 0.000 description 2
• BXNJHAXVSOCGBA-UHFFFAOYSA-N Harmine Chemical compound N1=CC=C2C3=CC=C(OC)C=C3NC2=C1C BXNJHAXVSOCGBA-UHFFFAOYSA-N 0.000 description 2
• NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
• RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 2
• NYMGNSNKLVNMIA-UHFFFAOYSA-N Iproniazid Chemical compound CC(C)NNC(=O)C1=CC=NC=C1 NYMGNSNKLVNMIA-UHFFFAOYSA-N 0.000 description 2
• YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 2
• 239000002147 L01XE04 - Sunitinib Substances 0.000 description 2
• IWMCPJZTADUIFX-UHFFFAOYSA-N LRRK2-IN-1 Chemical compound C=1C=C(NC=2N=C3N(C)C4=CC=CC=C4C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)N(CC1)CCC1N1CCN(C)CC1 IWMCPJZTADUIFX-UHFFFAOYSA-N 0.000 description 2
• 108010006444 Leucine-Rich Repeat Proteins Proteins 0.000 description 2
• 102000001291 MAP Kinase Kinase Kinase Human genes 0.000 description 2
• 102000043136 MAP kinase family Human genes 0.000 description 2
• 108091054455 MAP kinase family Proteins 0.000 description 2
• 108060006687 MAP kinase kinase kinase Proteins 0.000 description 2
• 206010026749 Mania Diseases 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• RLJFTICUTYVZDG-UHFFFAOYSA-N Methiothepine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2CC1N1CCN(C)CC1 RLJFTICUTYVZDG-UHFFFAOYSA-N 0.000 description 2
• 208000019695 Migraine disease Diseases 0.000 description 2
• 208000007101 Muscle Cramp Diseases 0.000 description 2
• 208000008238 Muscle Spasticity Diseases 0.000 description 2
• HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 2
• KYYIDSXMWOZKMP-UHFFFAOYSA-N O-desmethylvenlafaxine Chemical compound C1CCCCC1(O)C(CN(C)C)C1=CC=C(O)C=C1 KYYIDSXMWOZKMP-UHFFFAOYSA-N 0.000 description 2
• 208000037273 Pathologic Processes Diseases 0.000 description 2
• RMUCZJUITONUFY-UHFFFAOYSA-N Phenelzine Chemical compound NNCCC1=CC=CC=C1 RMUCZJUITONUFY-UHFFFAOYSA-N 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• 241000243142 Porifera Species 0.000 description 2
• 208000027030 Premenstrual dysphoric disease Diseases 0.000 description 2
• 206010036618 Premenstrual syndrome Diseases 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
• 208000029808 Psychomotor disease Diseases 0.000 description 2
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
• XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 description 2
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
• 208000005392 Spasm Diseases 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 description 2
• 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 description 2
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
• 229910052771 Terbium Inorganic materials 0.000 description 2
• 206010044565 Tremor Diseases 0.000 description 2
• HWHLPVGTWGOCJO-UHFFFAOYSA-N Trihexyphenidyl Chemical group C1CCCCC1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 HWHLPVGTWGOCJO-UHFFFAOYSA-N 0.000 description 2
• HGTDLKXUWVKLQX-UHFFFAOYSA-N [3-(hydroxymethyl)phenyl]boronic acid Chemical compound OCC1=CC=CC(B(O)O)=C1 HGTDLKXUWVKLQX-UHFFFAOYSA-N 0.000 description 2
• 239000002671 adjuvant Substances 0.000 description 2
• 239000000443 aerosol Substances 0.000 description 2
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
• VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 2
• 229960003805 amantadine Drugs 0.000 description 2
• 235000019270 ammonium chloride Nutrition 0.000 description 2
• RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
• 230000036506 anxiety Effects 0.000 description 2
• 238000000065 atmospheric pressure chemical ionisation Methods 0.000 description 2
• RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 2
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 description 2
• 230000008901 benefit Effects 0.000 description 2
• PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 2
• JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical class C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 2
• CPFJLLXFNPCTDW-BWSPSPBFSA-N benzatropine mesylate Chemical compound CS([O-])(=O)=O.O([C@H]1C[C@H]2CC[C@@H](C1)[NH+]2C)C(C=1C=CC=CC=1)C1=CC=CC=C1 CPFJLLXFNPCTDW-BWSPSPBFSA-N 0.000 description 2
• 125000004602 benzodiazinyl group Chemical group N1=NC(=CC2=C1C=CC=C2)* 0.000 description 2
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
• MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 2
• 230000037396 body weight Effects 0.000 description 2
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
• 208000029028 brain injury Diseases 0.000 description 2
• 210000000481 breast Anatomy 0.000 description 2
• 125000001246 bromo group Chemical group Br* 0.000 description 2
• 230000005587 bubbling Effects 0.000 description 2
• 239000000872 buffer Substances 0.000 description 2
• 210000004899 c-terminal region Anatomy 0.000 description 2
• XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
• MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 2
• 239000002775 capsule Substances 0.000 description 2
• QTAOMKOIBXZKND-PPHPATTJSA-N carbidopa Chemical compound O.NN[C@@](C(O)=O)(C)CC1=CC=C(O)C(O)=C1 QTAOMKOIBXZKND-PPHPATTJSA-N 0.000 description 2
• 229960004205 carbidopa Drugs 0.000 description 2
• 239000000969 carrier Substances 0.000 description 2
• 208000026106 cerebrovascular disease Diseases 0.000 description 2
• 239000000460 chlorine Substances 0.000 description 2
• 150000001805 chlorine compounds Chemical group 0.000 description 2
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical class C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 2
• 229960001231 choline Drugs 0.000 description 2
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 2
• 238000011260 co-administration Methods 0.000 description 2
• 230000008878 coupling Effects 0.000 description 2
• 238000010168 coupling process Methods 0.000 description 2
• 238000005859 coupling reaction Methods 0.000 description 2
• 239000006071 cream Substances 0.000 description 2
• 238000002425 crystallisation Methods 0.000 description 2
• 230000008025 crystallization Effects 0.000 description 2
• NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 2
• GUBNMFJOJGDCEL-UHFFFAOYSA-N dicyclomine hydrochloride Chemical compound [Cl-].C1CCCCC1C1(C(=O)OCC[NH+](CC)CC)CCCCC1 GUBNMFJOJGDCEL-UHFFFAOYSA-N 0.000 description 2
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical class CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
• HUPFGZXOMWLGNK-UHFFFAOYSA-N diflunisal Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C(=CC(F)=CC=2)F)=C1 HUPFGZXOMWLGNK-UHFFFAOYSA-N 0.000 description 2
• 229940043279 diisopropylamine Drugs 0.000 description 2
• ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
• 239000000534 dopa decarboxylase inhibitor Substances 0.000 description 2
• 231100000673 dose–response relationship Toxicity 0.000 description 2
• ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 2
• 239000012039 electrophile Substances 0.000 description 2
• 239000000839 emulsion Substances 0.000 description 2
• JRURYQJSLYLRLN-BJMVGYQFSA-N entacapone Chemical compound CCN(CC)C(=O)C(\C#N)=C\C1=CC(O)=C(O)C([N+]([O-])=O)=C1 JRURYQJSLYLRLN-BJMVGYQFSA-N 0.000 description 2
• 229960003337 entacapone Drugs 0.000 description 2
• 229940088598 enzyme Drugs 0.000 description 2
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
• LZPBLUATTGKZBH-UHFFFAOYSA-L fenoprofen calcium Chemical compound O.O.[Ca+2].[O-]C(=O)C(C)C1=CC=CC(OC=2C=CC=CC=2)=C1.[O-]C(=O)C(C)C1=CC=CC(OC=2C=CC=CC=2)=C1 LZPBLUATTGKZBH-UHFFFAOYSA-L 0.000 description 2
• 238000001914 filtration Methods 0.000 description 2
• 239000000796 flavoring agent Substances 0.000 description 2
• QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 2
• 235000013355 food flavoring agent Nutrition 0.000 description 2
• 239000012634 fragment Substances 0.000 description 2
• 229960003692 gamma aminobutyric acid Drugs 0.000 description 2
• 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
• 210000001035 gastrointestinal tract Anatomy 0.000 description 2
• 230000014509 gene expression Effects 0.000 description 2
• 208000016354 hearing loss disease Diseases 0.000 description 2
• 201000005787 hematologic cancer Diseases 0.000 description 2
• 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 2
• 125000000623 heterocyclic group Chemical group 0.000 description 2
• 229930195733 hydrocarbon Natural products 0.000 description 2
• 150000002430 hydrocarbons Chemical class 0.000 description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
• 229960001680 ibuprofen Drugs 0.000 description 2
• XZZXIYZZBJDEEP-UHFFFAOYSA-N imipramine hydrochloride Chemical compound [Cl-].C1CC2=CC=CC=C2N(CCC[NH+](C)C)C2=CC=CC=C21 XZZXIYZZBJDEEP-UHFFFAOYSA-N 0.000 description 2
• 239000007943 implant Substances 0.000 description 2
• 238000000338 in vitro Methods 0.000 description 2
• 125000001041 indolyl group Chemical group 0.000 description 2
• 230000006698 induction Effects 0.000 description 2
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
• 125000005438 isoindazolyl group Chemical group 0.000 description 2
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 2
• 238000002955 isolation Methods 0.000 description 2
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• 210000004901 leucine-rich repeat Anatomy 0.000 description 2
• TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 description 2
• 239000002502 liposome Substances 0.000 description 2
• 239000007788 liquid Substances 0.000 description 2
• 239000008297 liquid dosage form Substances 0.000 description 2
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
• 238000004519 manufacturing process Methods 0.000 description 2
• 239000000463 material Substances 0.000 description 2
• 229960003194 meglumine Drugs 0.000 description 2
• 229960004640 memantine Drugs 0.000 description 2
• 229910052751 metal Inorganic materials 0.000 description 2
• 239000002184 metal Substances 0.000 description 2
• 210000000274 microglia Anatomy 0.000 description 2
• 206010027599 migraine Diseases 0.000 description 2
• 229960004644 moclobemide Drugs 0.000 description 2
• 239000003607 modifier Substances 0.000 description 2
• 239000002808 molecular sieve Substances 0.000 description 2
• 239000006199 nebulizer Substances 0.000 description 2
• 210000002569 neuron Anatomy 0.000 description 2
• 229960002748 norepinephrine Drugs 0.000 description 2
• SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 2
• QVYRGXJJSLMXQH-UHFFFAOYSA-N orphenadrine Chemical compound C=1C=CC=C(C)C=1C(OCCN(C)C)C1=CC=CC=C1 QVYRGXJJSLMXQH-UHFFFAOYSA-N 0.000 description 2
• 229960001779 pargyline Drugs 0.000 description 2
• 229960002296 paroxetine Drugs 0.000 description 2
• 230000008506 pathogenesis Effects 0.000 description 2
• 230000009054 pathological process Effects 0.000 description 2
• 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 2
• 230000000144 pharmacologic effect Effects 0.000 description 2
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 2
• HZOTZTANVBDFOF-PBCQUBLHSA-N physostigmine salicylate Chemical compound OC(=O)C1=CC=CC=C1O.C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C HZOTZTANVBDFOF-PBCQUBLHSA-N 0.000 description 2
• 239000006187 pill Substances 0.000 description 2
• HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 2
• BIWOSRSKDCZIFM-UHFFFAOYSA-N piperidin-3-ol Chemical compound OC1CCCNC1 BIWOSRSKDCZIFM-UHFFFAOYSA-N 0.000 description 2
• 125000003386 piperidinyl group Chemical group 0.000 description 2
• 229910000160 potassium phosphate Inorganic materials 0.000 description 2
• 235000011009 potassium phosphates Nutrition 0.000 description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
• 230000008569 process Effects 0.000 description 2
• 239000003380 propellant Substances 0.000 description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 210000002307 prostate Anatomy 0.000 description 2
• 108090000623 proteins and genes Proteins 0.000 description 2
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 2
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 2
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
• RUOKEQAAGRXIBM-GFCCVEGCSA-N rasagiline Chemical compound C1=CC=C2[C@H](NCC#C)CCC2=C1 RUOKEQAAGRXIBM-GFCCVEGCSA-N 0.000 description 2
• 238000001953 recrystallisation Methods 0.000 description 2
• 102200092223 rs33939927 Human genes 0.000 description 2
• 201000000980 schizophrenia Diseases 0.000 description 2
• STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 2
• 208000012672 seasonal affective disease Diseases 0.000 description 2
• VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 2
• 230000001568 sexual effect Effects 0.000 description 2
• RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 2
• 208000019116 sleep disease Diseases 0.000 description 2
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
• QHJLLDJTVQAFAN-UHFFFAOYSA-M sodium meclofenamate monohydrate Chemical compound O.[Na+].CC1=CC=C(Cl)C(NC=2C(=CC=CC=2)C([O-])=O)=C1Cl QHJLLDJTVQAFAN-UHFFFAOYSA-M 0.000 description 2
• GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
• 239000007909 solid dosage form Substances 0.000 description 2
• 239000012453 solvate Substances 0.000 description 2
• 239000012086 standard solution Substances 0.000 description 2
• 239000007858 starting material Substances 0.000 description 2
• WINHZLLDWRZWRT-ATVHPVEESA-N sunitinib Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C WINHZLLDWRZWRT-ATVHPVEESA-N 0.000 description 2
• 229960001796 sunitinib Drugs 0.000 description 2
• 229940118176 surmontil Drugs 0.000 description 2
• 239000000375 suspending agent Substances 0.000 description 2
• 238000010189 synthetic method Methods 0.000 description 2
• 229960001685 tacrine Drugs 0.000 description 2
• GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 2
• 229940124597 therapeutic agent Drugs 0.000 description 2
• 230000001225 therapeutic effect Effects 0.000 description 2
• 125000001984 thiazolidinyl group Chemical group 0.000 description 2
• 229960005138 tianeptine Drugs 0.000 description 2
• QAXBVGVYDCAVLV-UHFFFAOYSA-N tiletamine Chemical compound C=1C=CSC=1C1(NCC)CCCCC1=O QAXBVGVYDCAVLV-UHFFFAOYSA-N 0.000 description 2
• 229960004603 tolcapone Drugs 0.000 description 2
• 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 2
• PHLBKPHSAVXXEF-UHFFFAOYSA-N trazodone Chemical compound ClC1=CC=CC(N2CCN(CCCN3C(N4C=CC=CC4=N3)=O)CC2)=C1 PHLBKPHSAVXXEF-UHFFFAOYSA-N 0.000 description 2
• 229960001032 trihexyphenidyl Drugs 0.000 description 2
• YDGHCKHAXOUQOS-BTJKTKAUSA-N trimipramine maleate Chemical compound [O-]C(=O)\C=C/C([O-])=O.C1CC2=CC=CC=C2[NH+](CC(C[NH+](C)C)C)C2=CC=CC=C21 YDGHCKHAXOUQOS-BTJKTKAUSA-N 0.000 description 2
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
• 229960000281 trometamol Drugs 0.000 description 2
• MDYOLVRUBBJPFM-UHFFFAOYSA-N tropolone Chemical compound OC1=CC=CC=CC1=O MDYOLVRUBBJPFM-UHFFFAOYSA-N 0.000 description 2
• PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 2
• 235000012431 wafers Nutrition 0.000 description 2
• 239000000080 wetting agent Substances 0.000 description 2
• 229910052725 zinc Chemical class 0.000 description 2
• 239000011701 zinc Chemical class 0.000 description 2
• DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 1
• OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 1
• MMAYTCMMKJYIAM-RUGRQLENSA-N (-)-voacangine Chemical compound C([C@H]1C[C@@H]([C@H]2[C@]3(C1)C(=O)OC)CC)N2CCC1=C3NC2=CC=C(OC)C=C12 MMAYTCMMKJYIAM-RUGRQLENSA-N 0.000 description 1
• IGLYMJRIWWIQQE-QUOODJBBSA-N (1S,2R)-2-phenylcyclopropan-1-amine (1R,2S)-2-phenylcyclopropan-1-amine Chemical compound N[C@H]1C[C@@H]1C1=CC=CC=C1.N[C@@H]1C[C@H]1C1=CC=CC=C1 IGLYMJRIWWIQQE-QUOODJBBSA-N 0.000 description 1
• KTGRHKOEFSJQNS-BDQAORGHSA-N (1s)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile;oxalic acid Chemical compound OC(=O)C(O)=O.C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 KTGRHKOEFSJQNS-BDQAORGHSA-N 0.000 description 1
• KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 1
• TWHNMSJGYKMTRB-KXYUELECSA-N (2r,3r)-2,3-dihydroxybutanedioic acid;2-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-methylphenol Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C)C=2)O)=CC=CC=C1 TWHNMSJGYKMTRB-KXYUELECSA-N 0.000 description 1
• RDJGLLICXDHJDY-NSHDSACASA-N (2s)-2-(3-phenoxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-NSHDSACASA-N 0.000 description 1
• NRNSHPCDKHOUOE-SNVBAGLBSA-N (2s)-2-amino-2-[(3,4-dihydroxyphenyl)methyl]-3-fluoropropanoic acid Chemical compound FC[C@@](N)(C(O)=O)CC1=CC=C(O)C(O)=C1 NRNSHPCDKHOUOE-SNVBAGLBSA-N 0.000 description 1
• 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 description 1
• LQMMFVPUIVBYII-YFKPBYRVSA-N (2s)-2-methylmorpholine Chemical compound C[C@H]1CNCCO1 LQMMFVPUIVBYII-YFKPBYRVSA-N 0.000 description 1
• JQQWDYJWDCIVKQ-QUCCMNQESA-N (3r,4s)-3-(4-benzyl-4-hydroxypiperidin-1-yl)-3,4-dihydro-2h-chromene-4,7-diol Chemical compound C1CN([C@H]2[C@H](C3=CC=C(O)C=C3OC2)O)CCC1(O)CC1=CC=CC=C1 JQQWDYJWDCIVKQ-QUCCMNQESA-N 0.000 description 1
• DIJAKMCTWBGMNQ-RGMNGODLSA-N (3s)-3-methylpiperidine;hydrochloride Chemical compound Cl.C[C@H]1CCCNC1 DIJAKMCTWBGMNQ-RGMNGODLSA-N 0.000 description 1
• LBJYPLZODCWHKE-GOSISDBHSA-N (4r)-4-cyclopropyl-8-fluoro-5-[6-(trifluoromethyl)pyridin-3-yl]sulfonyl-1,4-dihydropyrazolo[4,3-c]quinoline Chemical compound C1([C@H]2N(C3=CC=C(C=C3C=3NN=CC=32)F)S(=O)(=O)C=2C=NC(=CC=2)C(F)(F)F)CC1 LBJYPLZODCWHKE-GOSISDBHSA-N 0.000 description 1
• DQNMZSIJHFEYTM-LEWJYISDSA-N (4s,5r)-3-[3-(azepan-1-yl)propyl]-4-(2-methylpropyl)-5-phenyl-1,3-oxazolidin-2-one Chemical compound O([C@@H]([C@@H]1CC(C)C)C=2C=CC=CC=2)C(=O)N1CCCN1CCCCCC1 DQNMZSIJHFEYTM-LEWJYISDSA-N 0.000 description 1
• GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
• WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 description 1
• RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 description 1
• SYTBZMRGLBWNTM-SNVBAGLBSA-N (R)-flurbiprofen Chemical compound FC1=CC([C@H](C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-SNVBAGLBSA-N 0.000 description 1
• RKUNBYITZUJHSG-FXUDXRNXSA-N (S)-atropine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@H]3CC[C@@H](C2)N3C)=CC=CC=C1 RKUNBYITZUJHSG-FXUDXRNXSA-N 0.000 description 1
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
• YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 description 1
• LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
• 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 1
• VOJUXHHACRXLTD-UHFFFAOYSA-N 1,4-dihydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC(O)=C21 VOJUXHHACRXLTD-UHFFFAOYSA-N 0.000 description 1
• RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• CKAKVKWRMCAYJD-UHFFFAOYSA-N 1-(3-ethylphenyl)-1-methyl-2-naphthalen-1-ylguanidine;hydrochloride Chemical compound Cl.CCC1=CC=CC(N(C)C(N)=NC=2C3=CC=CC=C3C=CC=2)=C1 CKAKVKWRMCAYJD-UHFFFAOYSA-N 0.000 description 1
• BJBMICJVJIETOV-UHFFFAOYSA-N 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole Chemical compound O1C(C)(C)C(C)(C)OB1N1N=CC=C1 BJBMICJVJIETOV-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• MAYQIFVKVAUMPD-UHFFFAOYSA-N 1-(benzenesulfonyl)-2-methyl-4-piperazin-1-ylbenzimidazole Chemical compound CC1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1 MAYQIFVKVAUMPD-UHFFFAOYSA-N 0.000 description 1
• QEMSVZNTSXPFJA-HNAYVOBHSA-N 1-[(1s,2s)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]-4-phenylpiperidin-4-ol Chemical compound C1([C@H](O)[C@H](C)N2CCC(O)(CC2)C=2C=CC=CC=2)=CC=C(O)C=C1 QEMSVZNTSXPFJA-HNAYVOBHSA-N 0.000 description 1
• WSEQXVZVJXJVFP-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCCN(C)C)C1=CC=C(F)C=C1 WSEQXVZVJXJVFP-UHFFFAOYSA-N 0.000 description 1
• WIHMBLDNRMIGDW-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile;hydron;bromide Chemical compound [Br-].O1CC2=CC(C#N)=CC=C2C1(CCC[NH+](C)C)C1=CC=C(F)C=C1 WIHMBLDNRMIGDW-UHFFFAOYSA-N 0.000 description 1
• MLBHFBKZUPLWBD-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]-2-propanamine Chemical compound CC(N)CC1=CC=CC(C(F)(F)F)=C1 MLBHFBKZUPLWBD-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• 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 description 1
• 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 description 1
• 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 description 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 description 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 description 1
• 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 description 1
• VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
• VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical compound CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• 125000004486 1-methylpiperidin-3-yl group Chemical group CN1CC(CCC1)* 0.000 description 1
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
• IPDWABJNXLNLRA-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)C(O)C(O)C(O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O IPDWABJNXLNLRA-UHFFFAOYSA-N 0.000 description 1
• YBAWYTYNMZWMMJ-UHFFFAOYSA-N 2-(6-fluoro-1h-indol-3-yl)-n-[[3-(2,2,3,3-tetrafluoropropoxy)phenyl]methyl]ethanamine Chemical compound FC(F)C(F)(F)COC1=CC=CC(CNCCC=2C3=CC=C(F)C=C3NC=2)=C1 YBAWYTYNMZWMMJ-UHFFFAOYSA-N 0.000 description 1
• XNIOWJUQPMKCIJ-UHFFFAOYSA-N 2-(benzylamino)ethanol Chemical compound OCCNCC1=CC=CC=C1 XNIOWJUQPMKCIJ-UHFFFAOYSA-N 0.000 description 1
• BPXKZEMBEZGUAH-UHFFFAOYSA-N 2-(chloromethoxy)ethyl-trimethylsilane Chemical compound C[Si](C)(C)CCOCCl BPXKZEMBEZGUAH-UHFFFAOYSA-N 0.000 description 1
• LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
• URVCCOOEISXCHF-UHFFFAOYSA-N 2-[(2-iodopyrrolo[2,3-d]pyrimidin-7-yl)methoxy]ethyl-trimethylsilane Chemical compound IC=1N=CC2=C(N=1)N(C=C2)COCC[Si](C)(C)C URVCCOOEISXCHF-UHFFFAOYSA-N 0.000 description 1
• LFWHFZJPXXOYNR-RQZCQDPDSA-N 2-[(3e)-6-fluoro-2-methyl-3-[(4-methylsulfanylphenyl)methylidene]inden-1-yl]acetic acid Chemical compound C1=CC(SC)=CC=C1\C=C/1C2=CC=C(F)C=C2C(CC(O)=O)=C\1C LFWHFZJPXXOYNR-RQZCQDPDSA-N 0.000 description 1
• RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 1
• UEBBYLJZCHTLEG-UTKZUKDTSA-N 2-[[(1r,2s)-6-methoxy-1-phenyl-1,2,3,4-tetrahydronaphthalen-2-yl]methyl-methylamino]acetic acid Chemical compound C1([C@@H]2C3=CC=C(C=C3CC[C@@H]2CN(C)CC(O)=O)OC)=CC=CC=C1 UEBBYLJZCHTLEG-UTKZUKDTSA-N 0.000 description 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 description 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 description 1
• GTPYPGWTKZAMCX-OAHLLOKOSA-N 2-fluoro-3-[4-[(2r)-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([C@@H]2OCCN(C2)C=2C=3C(C=4C(=C(C#N)C=CC=4)F)=CNC=3N=CN=2)=N1 GTPYPGWTKZAMCX-OAHLLOKOSA-N 0.000 description 1
• GTPYPGWTKZAMCX-HNNXBMFYSA-N 2-fluoro-3-[4-[(2s)-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([C@H]2OCCN(C2)C=2C=3C(C=4C(=C(C#N)C=CC=4)F)=CNC=3N=CN=2)=N1 GTPYPGWTKZAMCX-HNNXBMFYSA-N 0.000 description 1
• 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 description 1
• 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 description 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 description 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 description 1
• PPBWDPPUKPVDQL-UHFFFAOYSA-N 2-methyl-3-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound CC1=C(C#N)C=CC=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 PPBWDPPUKPVDQL-UHFFFAOYSA-N 0.000 description 1
• LAEVHNHECWJRFL-UHFFFAOYSA-N 2-methyl-5-(4-morpholin-4-yl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)pyrazole-3-carbonitrile Chemical compound C1=C(C#N)N(C)N=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 LAEVHNHECWJRFL-UHFFFAOYSA-N 0.000 description 1
• LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
• WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• OFKWWALNMPEOSZ-UHFFFAOYSA-N 3-(hydrazinylmethyl)phenol Chemical compound NNCC1=CC=CC(O)=C1 OFKWWALNMPEOSZ-UHFFFAOYSA-N 0.000 description 1
• IXICFQPOLVNLBK-UHFFFAOYSA-N 3-[4-(1h-pyrazol-4-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2C3=C(NC4=CNN=C4)N=CN=C3NC=2)=C1 IXICFQPOLVNLBK-UHFFFAOYSA-N 0.000 description 1
• RFDOWEJYIPXXRM-UHFFFAOYSA-N 3-[4-(2,2-dimethylmorpholin-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1COC(C)(C)CN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 RFDOWEJYIPXXRM-UHFFFAOYSA-N 0.000 description 1
• YWMMOZWNNJVCTG-UHFFFAOYSA-N 3-[4-(2-ethylmorpholin-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1COC(CC)CN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 YWMMOZWNNJVCTG-UHFFFAOYSA-N 0.000 description 1
• RQRXAEJJSVVQHF-UHFFFAOYSA-N 3-[4-(2-morpholin-4-ylethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2C3=C(NCCN4CCOCC4)N=CN=C3NC=2)=C1 RQRXAEJJSVVQHF-UHFFFAOYSA-N 0.000 description 1
• RZRWSNMIDNLNTM-UHFFFAOYSA-N 3-[4-(2-oxa-9-azaspiro[4.5]decan-9-yl)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2C3=C(N4CC5(COCC5)CCC4)N=CN=C3NC=2)=C1 RZRWSNMIDNLNTM-UHFFFAOYSA-N 0.000 description 1
• MAXRJKNDOJGUOO-UHFFFAOYSA-N 3-[4-(2-pyrimidin-4-ylmorpholin-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2C3=C(N4CC(OCC4)C=4N=CN=CC=4)N=CN=C3NC=2)=C1 MAXRJKNDOJGUOO-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• FOIRQTHDJDRMKY-UHFFFAOYSA-N 3-[4-(3,3-difluoropyrrolidin-1-yl)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1C(F)(F)CCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 FOIRQTHDJDRMKY-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• 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 description 1
• 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 description 1
• 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 description 1
• XDLWXDDVQIGMJO-UHFFFAOYSA-N 3-[4-(3-methoxypiperidin-1-yl)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1C(OC)CCCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 XDLWXDDVQIGMJO-UHFFFAOYSA-N 0.000 description 1
• RRUCJMTTXOEWQO-UHFFFAOYSA-N 3-[4-(3-oxo-2,7-diazaspiro[4.5]decan-7-yl)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1NC(=O)CC21CN(C=1C=3C(C=4C=C(C=CC=4)C#N)=CNC=3N=CN=1)CCC2 RRUCJMTTXOEWQO-UHFFFAOYSA-N 0.000 description 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 description 1
• QSSCZIVWHWTPLQ-UHFFFAOYSA-N 3-[4-(4,4-difluoropiperidin-1-yl)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1CC(F)(F)CCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 QSSCZIVWHWTPLQ-UHFFFAOYSA-N 0.000 description 1
• GNJXZANIHLYXSG-UHFFFAOYSA-N 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=CC=1)C#N)=CN2 GNJXZANIHLYXSG-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• YKKOQHHGVRLNIF-UHFFFAOYSA-N 3-[4-(4-methylpiperidin-1-yl)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1CC(C)CCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 YKKOQHHGVRLNIF-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• UQVOQPAIMMMRAM-UHFFFAOYSA-N 3-[4-(6-oxa-3-azabicyclo[3.1.1]heptan-3-yl)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2C3=C(N4CC5CC(O5)C4)N=CN=C3NC=2)=C1 UQVOQPAIMMMRAM-UHFFFAOYSA-N 0.000 description 1
• HEZSSKBBLQBTMF-UHFFFAOYSA-N 3-[4-(9-methyl-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1CN(C)CCC21OCCN(C=1C=3C(C=4C=C(C=CC=4)C#N)=CNC=3N=CN=1)C2 HEZSSKBBLQBTMF-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• JQMHPASIGUDQDB-UHFFFAOYSA-N 3-[4-(dimethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-2-fluorobenzonitrile Chemical compound C1=2C(N(C)C)=NC=NC=2NC=C1C1=CC=CC(C#N)=C1F JQMHPASIGUDQDB-UHFFFAOYSA-N 0.000 description 1
• RNFUZCRIGVXDNJ-UHFFFAOYSA-N 3-[4-(dimethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-4-fluorobenzonitrile Chemical compound C1=2C(N(C)C)=NC=NC=2NC=C1C1=CC(C#N)=CC=C1F RNFUZCRIGVXDNJ-UHFFFAOYSA-N 0.000 description 1
• RSAHPQFMIGMKRC-UHFFFAOYSA-N 3-[4-(dimethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1C1=CNC2=NC=NC(N(C)C)=C12 RSAHPQFMIGMKRC-UHFFFAOYSA-N 0.000 description 1
• HSYAZHAPKUYSIM-UHFFFAOYSA-N 3-[4-(dimethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-5-fluorobenzonitrile Chemical compound C1=2C(N(C)C)=NC=NC=2NC=C1C1=CC(F)=CC(C#N)=C1 HSYAZHAPKUYSIM-UHFFFAOYSA-N 0.000 description 1
• DMBPKDDBYKIOKU-UHFFFAOYSA-N 3-[4-(dimethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-5-methoxybenzonitrile Chemical compound COC1=CC(C#N)=CC(C=2C3=C(N(C)C)N=CN=C3NC=2)=C1 DMBPKDDBYKIOKU-UHFFFAOYSA-N 0.000 description 1
• KUPZVVVTRUKMHE-UHFFFAOYSA-N 3-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1=2C(NC)=NC=NC=2NC=C1C1=CC=CC(C#N)=C1 KUPZVVVTRUKMHE-UHFFFAOYSA-N 0.000 description 1
• PPIDYHAZFFBKOT-OAHLLOKOSA-N 3-[4-[(2r)-2-(methoxymethyl)morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1CO[C@@H](COC)CN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 PPIDYHAZFFBKOT-OAHLLOKOSA-N 0.000 description 1
• PPIDYHAZFFBKOT-HNNXBMFYSA-N 3-[4-[(2s)-2-(methoxymethyl)morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1CO[C@H](COC)CN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 PPIDYHAZFFBKOT-HNNXBMFYSA-N 0.000 description 1
• CTQLDDHACGXLAE-CQSZACIVSA-N 3-[4-[(3r)-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-CQSZACIVSA-N 0.000 description 1
• WVOMGQLDVCJODR-CYBMUJFWSA-N 3-[4-[(3r)-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=CC=1)C#N)=CN2 WVOMGQLDVCJODR-CYBMUJFWSA-N 0.000 description 1
• OKUUUFUWBALHGR-GFCCVEGCSA-N 3-[4-[(3r)-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-GFCCVEGCSA-N 0.000 description 1
• 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 description 1
• 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 description 1
• 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 description 1
• ZGKSOMYBGWFPQQ-LBPRGKRZSA-N 3-[4-[(3s)-3-methylpiperidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzenesulfonamide Chemical compound C1[C@@H](C)CCCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)S(N)(=O)=O)=CN2 ZGKSOMYBGWFPQQ-LBPRGKRZSA-N 0.000 description 1
• 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 description 1
• WVOMGQLDVCJODR-ZDUSSCGKSA-N 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=CC=1)C#N)=CN2 WVOMGQLDVCJODR-ZDUSSCGKSA-N 0.000 description 1
• 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 description 1
• 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 description 1
• CHDYFKIOVVSYLO-OKILXGFUSA-N 3-[4-[(3s,5r)-3,5-dimethylpiperidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1C1=CNC2=NC=NC(N3C[C@H](C)C[C@H](C)C3)=C12 CHDYFKIOVVSYLO-OKILXGFUSA-N 0.000 description 1
• NERVYHZAYISIMC-UHFFFAOYSA-N 3-[4-[2-(1,2-oxazol-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)C=4ON=CC=4)N=CN=C3NC=2)=C1 NERVYHZAYISIMC-UHFFFAOYSA-N 0.000 description 1
• TUPFGHYCHSDHDW-UHFFFAOYSA-N 3-[4-[2-(1,3-thiazol-2-yl)morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2C3=C(N4CC(OCC4)C=4SC=CN=4)N=CN=C3NC=2)=C1 TUPFGHYCHSDHDW-UHFFFAOYSA-N 0.000 description 1
• SZESNRCIFHHUGA-UHFFFAOYSA-N 3-[4-[2-(3-cyclopropyl-1,2,4-oxadiazol-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)C=4ON=C(N=4)C4CC4)N=CN=C3NC=2)=C1 SZESNRCIFHHUGA-UHFFFAOYSA-N 0.000 description 1
• CZQDUHIXGSFBGB-UHFFFAOYSA-N 3-[4-[2-(3-hydroxyphenyl)morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound OC1=CC=CC(C2OCCN(C2)C=2C=3C(C=4C=C(C=CC=4)C#N)=CNC=3N=CN=2)=C1 CZQDUHIXGSFBGB-UHFFFAOYSA-N 0.000 description 1
• YSXZVUXTUVKHPF-UHFFFAOYSA-N 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=CC=4)C#N)=CNC=3N=CN=2)=N1 YSXZVUXTUVKHPF-UHFFFAOYSA-N 0.000 description 1
• WYGOKSXLCGKFHF-UHFFFAOYSA-N 3-[4-[2-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2C3=C(N4CC(OCC4)C=4N=C(ON=4)C4CC4)N=CN=C3NC=2)=C1 WYGOKSXLCGKFHF-UHFFFAOYSA-N 0.000 description 1
• OVLGSAZYDZSQMN-UHFFFAOYSA-N 3-[4-[2-(cyanomethyl)morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1COC(CC#N)CN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 OVLGSAZYDZSQMN-UHFFFAOYSA-N 0.000 description 1
• PPIDYHAZFFBKOT-UHFFFAOYSA-N 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=CC=1)C#N)=CN2 PPIDYHAZFFBKOT-UHFFFAOYSA-N 0.000 description 1
• YXNMHCJGLJBGCK-UHFFFAOYSA-N 3-[4-[2-[(3-cyanophenoxy)methyl]morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound N#CC1=CC=CC(OCC2OCCN(C2)C=2C=3C(C=4C=C(C=CC=4)C#N)=CNC=3N=CN=2)=C1 YXNMHCJGLJBGCK-UHFFFAOYSA-N 0.000 description 1
• KPOYYDYAIZZVSV-UHFFFAOYSA-N 3-[4-[2-[(dimethylamino)methyl]morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1COC(CN(C)C)CN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 KPOYYDYAIZZVSV-UHFFFAOYSA-N 0.000 description 1
• MACFGBHDXKXMCB-UHFFFAOYSA-N 3-[4-[2-[[5-(difluoromethyl)-1,2,4-oxadiazol-3-yl]methyl]morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound O1C(C(F)F)=NC(CC2OCCN(C2)C=2C=3C(C=4C=C(C=CC=4)C#N)=CNC=3N=CN=2)=N1 MACFGBHDXKXMCB-UHFFFAOYSA-N 0.000 description 1
• KJNNWYBAOPXVJY-UHFFFAOYSA-N 3-[4-[2-butyl-1-[4-(4-chlorophenoxy)phenyl]imidazol-4-yl]phenoxy]-n,n-diethylpropan-1-amine Chemical compound CCCCC1=NC(C=2C=CC(OCCCN(CC)CC)=CC=2)=CN1C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 KJNNWYBAOPXVJY-UHFFFAOYSA-N 0.000 description 1
• PJPNUCDUTMFJAC-UHFFFAOYSA-N 3-[4-[3-(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(N4CC(CCC4)C=4NC=CN=4)N=CN=C3NC=2)=C1 PJPNUCDUTMFJAC-UHFFFAOYSA-N 0.000 description 1
• UBMJBDJEXHOQAA-UHFFFAOYSA-N 3-[4-[3-(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(N4CC(CCC4)C4=NNC=C4)N=CN=C3NC=2)=C1 UBMJBDJEXHOQAA-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• SGDNLMNAWOAVJR-UHFFFAOYSA-N 3-[4-[3-(methoxymethyl)piperidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1C(COC)CCCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 SGDNLMNAWOAVJR-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• 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 description 1
• NZMIMYYOIMLCGU-UHFFFAOYSA-N 3-[4-[4-fluoro-4-(hydroxymethyl)piperidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1CC(CO)(F)CCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 NZMIMYYOIMLCGU-UHFFFAOYSA-N 0.000 description 1
• UUUKPLOXHGVXRE-UHFFFAOYSA-N 3-[6-formyl-4-morpholin-4-yl-7-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C12=C(N3CCOCC3)N=CN=C2N(COCC[Si](C)(C)C)C(C=O)=C1C1=CC=CC(C#N)=C1 UUUKPLOXHGVXRE-UHFFFAOYSA-N 0.000 description 1
• PTFROQWWLWEYKP-UHFFFAOYSA-N 3-amino-3-[5-(3-cyanophenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-N,N-dimethylpropanamide Chemical compound C(#N)C=1C=C(C=CC=1)C1=CNC=2N=CN=C(C=21)C(N)CC(=O)N(C)C PTFROQWWLWEYKP-UHFFFAOYSA-N 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 description 1
• ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 1
• WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 1
• XMIIGOLPHOKFCH-UHFFFAOYSA-M 3-phenylpropionate Chemical compound [O-]C(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-M 0.000 description 1
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
• RGEQUVWPMKHSRY-UHFFFAOYSA-N 4-(3-fluoropiperidin-1-yl)-5-(1-methylpyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1=NN(C)C=C1C1=CNC2=NC=NC(N3CC(F)CCC3)=C12 RGEQUVWPMKHSRY-UHFFFAOYSA-N 0.000 description 1
• CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
• 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 description 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 description 1
• XXYOOXZHWJEEHQ-UHFFFAOYSA-N 4-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)-1h-pyridin-2-one Chemical compound C1=CNC(=O)C=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 XXYOOXZHWJEEHQ-UHFFFAOYSA-N 0.000 description 1
• RAEFZMMRMAQKHT-UHFFFAOYSA-N 4-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)thiophene-2-carbonitrile Chemical compound S1C(C#N)=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 RAEFZMMRMAQKHT-UHFFFAOYSA-N 0.000 description 1
• UJEUJDBAYJPPLN-UHFFFAOYSA-N 4-(5-imidazo[2,1-b][1,3]thiazol-5-yl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)morpholine Chemical compound C1COCCN1C1=NC=NC2=C1C(C=1N3C=CSC3=NC=1)=CN2 UJEUJDBAYJPPLN-UHFFFAOYSA-N 0.000 description 1
• DDZHVRFUDGVWMJ-UHFFFAOYSA-N 4-(5-pyrazolo[1,5-a]pyridin-3-yl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)morpholine Chemical compound C1COCCN1C1=NC=NC2=C1C(C1=C3C=CC=CN3N=C1)=CN2 DDZHVRFUDGVWMJ-UHFFFAOYSA-N 0.000 description 1
• ZONYIIVYWCZHAS-UHFFFAOYSA-N 4-(5-pyrazolo[1,5-a]pyrimidin-3-yl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)morpholine Chemical compound C1COCCN1C1=NC=NC2=C1C(C1=C3N=CC=CN3N=C1)=CN2 ZONYIIVYWCZHAS-UHFFFAOYSA-N 0.000 description 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 description 1
• CJNIPZKAWCOYRR-NSHDSACASA-N 4-[(3s)-3-fluoropyrrolidin-1-yl]-5-(2-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound COC1=CC=CC=C1C1=CNC2=NC=NC(N3C[C@@H](F)CC3)=C12 CJNIPZKAWCOYRR-NSHDSACASA-N 0.000 description 1
• 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 description 1
• AJXZFJQZUDXGFM-LBPRGKRZSA-N 4-[(3s)-3-methylpiperidin-1-yl]-5-(1h-pyrrolo[2,3-b]pyridin-5-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1[C@@H](C)CCCN1C1=NC=NC2=C1C(C=1C=C3C=CN=C3NC=1)=CN2 AJXZFJQZUDXGFM-LBPRGKRZSA-N 0.000 description 1
• 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 description 1
• 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 description 1
• AMGLEELZBJNIIZ-ZDUSSCGKSA-N 4-[(3s)-3-methylpiperidin-1-yl]-5-phenyl-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1[C@@H](C)CCCN1C1=NC=NC2=C1C(C=1C=CC=CC=1)=CN2 AMGLEELZBJNIIZ-ZDUSSCGKSA-N 0.000 description 1
• OLOPFQBPHVBUAY-LBPRGKRZSA-N 4-[(3s)-3-methylpiperidin-1-yl]-5-pyridin-3-yl-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1[C@@H](C)CCCN1C1=NC=NC2=C1C(C=1C=NC=CC=1)=CN2 OLOPFQBPHVBUAY-LBPRGKRZSA-N 0.000 description 1
• 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 description 1
• DJYBFRXIESTXBV-LBPRGKRZSA-N 4-[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=CC(=CC=1)C(N)=O)=CN2 DJYBFRXIESTXBV-LBPRGKRZSA-N 0.000 description 1
• MOSVQOBFLZHZNS-LBPRGKRZSA-N 4-[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=CC(O)=CC=1)=CN2 MOSVQOBFLZHZNS-LBPRGKRZSA-N 0.000 description 1
• UFGFEUGHLUNUTL-UHFFFAOYSA-N 4-[5-(1-methylpyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]-2-[(6-methylpyridin-3-yl)oxymethyl]morpholine Chemical compound C1=NC(C)=CC=C1OCC1OCCN(C=2C=3C(C4=CN(C)N=C4)=CNC=3N=CN=2)C1 UFGFEUGHLUNUTL-UHFFFAOYSA-N 0.000 description 1
• PVMURCNOAKOEIY-UHFFFAOYSA-N 4-[5-(1-methylpyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]thiomorpholine Chemical compound C1=NN(C)C=C1C1=CNC2=NC=NC(N3CCSCC3)=C12 PVMURCNOAKOEIY-UHFFFAOYSA-N 0.000 description 1
• YDRMVAPJCHICGE-UHFFFAOYSA-N 4-[5-(3-cyanophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine-2-carbonitrile Chemical compound C1COC(C#N)CN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 YDRMVAPJCHICGE-UHFFFAOYSA-N 0.000 description 1
• SURQEPAOBKWDSC-UHFFFAOYSA-N 4-[5-(5-fluoro-2-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]-2-(5-methyl-1,2,4-oxadiazol-3-yl)morpholine Chemical compound COC1=CC=C(F)C=C1C1=CNC2=NC=NC(N3CC(OCC3)C=3N=C(C)ON=3)=C12 SURQEPAOBKWDSC-UHFFFAOYSA-N 0.000 description 1
• OWQJWDZUYOCCTM-UHFFFAOYSA-N 4-[5-(6-methylimidazo[2,1-b][1,3]thiazol-5-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound CC=1N=C2SC=CN2C=1C(C=12)=CNC2=NC=NC=1N1CCOCC1 OWQJWDZUYOCCTM-UHFFFAOYSA-N 0.000 description 1
• NFJFKJKNVKJOOR-UHFFFAOYSA-N 4-[6-methyl-5-(1-methylpyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C=12C(C3=CN(C)N=C3)=C(C)NC2=NC=NC=1N1CCOCC1 NFJFKJKNVKJOOR-UHFFFAOYSA-N 0.000 description 1
• HVBSAKJJOYLTQU-UHFFFAOYSA-M 4-aminobenzenesulfonate Chemical compound NC1=CC=C(S([O-])(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-M 0.000 description 1
• HCFJHJBEGJJOMO-UHFFFAOYSA-N 4-chloro-2-methyl-7h-pyrrolo[2,3-d]pyrimidine Chemical compound CC1=NC(Cl)=C2C=CNC2=N1 HCFJHJBEGJJOMO-UHFFFAOYSA-N 0.000 description 1
• BPTCCCTWWAUJRK-UHFFFAOYSA-N 4-chloro-7h-pyrrolo[2,3-d]pyrimidine Chemical compound ClC1=NC=NC2=C1C=CN2 BPTCCCTWWAUJRK-UHFFFAOYSA-N 0.000 description 1
• NRPQELCNMADTOZ-OAQYLSRUSA-N 4-cyano-n-[(2r)-2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]propyl]-n-pyridin-2-ylbenzamide Chemical compound C([C@@H](C)N1CCN(CC1)C=1C=2OCCOC=2C=CC=1)N(C=1N=CC=CC=1)C(=O)C1=CC=C(C#N)C=C1 NRPQELCNMADTOZ-OAQYLSRUSA-N 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 1
• KMYQVQCPFIBPJU-UHFFFAOYSA-N 4-methoxy-3-[4-(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(N3CC(C)CCC3)=C12 KMYQVQCPFIBPJU-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
• BVJKIJWYMMWEGO-LBPRGKRZSA-N 5-(1h-indazol-4-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=3C=NNC=3C=CC=1)=CN2 BVJKIJWYMMWEGO-LBPRGKRZSA-N 0.000 description 1
• 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 description 1
• SLHUEJGOPQQROH-NSHDSACASA-N 5-(2-chloro-5-methylpyridin-3-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(=NC=C(C)C=1)Cl)=CN2 SLHUEJGOPQQROH-NSHDSACASA-N 0.000 description 1
• QBRZGGWZMVWKAL-UHFFFAOYSA-N 5-(2-fluoro-6-methoxyphenyl)-n,n-dimethyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound COC1=CC=CC(F)=C1C1=CNC2=NC=NC(N(C)C)=C12 QBRZGGWZMVWKAL-UHFFFAOYSA-N 0.000 description 1
• 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 description 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 description 1
• 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 description 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 description 1
• 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 description 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 description 1
• DBAPKCRYCKRGER-UHFFFAOYSA-N 5-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)thiophene-2-carbonitrile Chemical compound S1C(C#N)=CC=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 DBAPKCRYCKRGER-UHFFFAOYSA-N 0.000 description 1
• VPDCXVHVQYRNQA-UHFFFAOYSA-N 5-(5-chloro-2-methoxyphenyl)-n,n-dimethyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound COC1=CC=C(Cl)C=C1C1=CNC2=NC=NC(N(C)C)=C12 VPDCXVHVQYRNQA-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
• BUEFNMDRBNJXBV-NSHDSACASA-N 5-(5-fluoro-2-methoxyphenyl)-4-[(3s)-3-fluoropyrrolidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound COC1=CC=C(F)C=C1C1=CNC2=NC=NC(N3C[C@@H](F)CC3)=C12 BUEFNMDRBNJXBV-NSHDSACASA-N 0.000 description 1
• XZUOESLVSZMYCZ-UHFFFAOYSA-N 5-(5-fluoro-2-methoxyphenyl)-n,n-dimethyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound COC1=CC=C(F)C=C1C1=CNC2=NC=NC(N(C)C)=C12 XZUOESLVSZMYCZ-UHFFFAOYSA-N 0.000 description 1
• GJCDCQIHBGSBQM-NSHDSACASA-N 5-(6-fluoro-5-methylpyridin-3-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=C(C)C(F)=NC=1)=CN2 GJCDCQIHBGSBQM-NSHDSACASA-N 0.000 description 1
• QNWOSJAGFSUDFE-UHFFFAOYSA-N 5-(aminooxymethyl)-2-bromophenol Chemical compound NOCC1=CC=C(Br)C(O)=C1 QNWOSJAGFSUDFE-UHFFFAOYSA-N 0.000 description 1
• MXUNKHLAEDCYJL-UHFFFAOYSA-N 5-(hydroxymethyl)-3-(3-methylphenyl)-1,3-oxazolidin-2-one Chemical compound CC1=CC=CC(N2C(OC(CO)C2)=O)=C1 MXUNKHLAEDCYJL-UHFFFAOYSA-N 0.000 description 1
• HLHHFQYQMDENFH-LBPRGKRZSA-N 5-[4-[(3s)-3-methylpiperidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-2,3-dihydroisoindol-1-one Chemical compound C1[C@@H](C)CCCN1C1=NC=NC2=C1C(C=1C=C3CNC(=O)C3=CC=1)=CN2 HLHHFQYQMDENFH-LBPRGKRZSA-N 0.000 description 1
• OXLMTRZWMHIZBY-UHFFFAOYSA-N 5-bromo-4-chloro-7h-pyrrolo[2,3-d]pyrimidine Chemical compound ClC1=NC=NC2=C1C(Br)=CN2 OXLMTRZWMHIZBY-UHFFFAOYSA-N 0.000 description 1
• QQWUGDVOUVUTOY-UHFFFAOYSA-N 5-chloro-N2-[2-methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-(2-propan-2-ylsulfonylphenyl)pyrimidine-2,4-diamine Chemical compound COC1=CC(N2CCC(CC2)N2CCN(C)CC2)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1S(=O)(=O)C(C)C QQWUGDVOUVUTOY-UHFFFAOYSA-N 0.000 description 1
• YNFMDHPLZLCRAS-UHFFFAOYSA-N 5-phenyl-4-pyrrolidin-1-yl-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1CCCN1C1=NC=NC2=C1C(C=1C=CC=CC=1)=CN2 YNFMDHPLZLCRAS-UHFFFAOYSA-N 0.000 description 1
• FCBQJNCAKZSIAH-UHFFFAOYSA-N 6-[2-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]ethylsulfinyl]-3h-1,3-benzoxazol-2-one Chemical compound C1=CC(F)=CC=C1CC1CCN(CCS(=O)C=2C=C3OC(=O)NC3=CC=2)CC1 FCBQJNCAKZSIAH-UHFFFAOYSA-N 0.000 description 1
• BGQYGARAMFXWSE-LBPRGKRZSA-N 6-[4-[(3s)-3-methylpiperidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-2,3-dihydroisoindol-1-one Chemical compound C1[C@@H](C)CCCN1C1=NC=NC2=C1C(C=1C=C3C(=O)NCC3=CC=1)=CN2 BGQYGARAMFXWSE-LBPRGKRZSA-N 0.000 description 1
• HNEBPTAKURBYRM-UHFFFAOYSA-N 6-bromopyridine-2-carbonitrile Chemical compound BrC1=CC=CC(C#N)=N1 HNEBPTAKURBYRM-UHFFFAOYSA-N 0.000 description 1
• FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
• 229930000680 A04AD01 - Scopolamine Natural products 0.000 description 1
• 206010065040 AIDS dementia complex Diseases 0.000 description 1
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• 229940100578 Acetylcholinesterase inhibitor Drugs 0.000 description 1
• 208000031261 Acute myeloid leukaemia Diseases 0.000 description 1
• 208000017194 Affective disease Diseases 0.000 description 1
• 241001251200 Agelas Species 0.000 description 1
• 208000008811 Agoraphobia Diseases 0.000 description 1
• 208000007848 Alcoholism Diseases 0.000 description 1
• 208000000044 Amnesia Diseases 0.000 description 1
• 208000031091 Amnestic disease Diseases 0.000 description 1
• 208000029197 Amphetamine-Related disease Diseases 0.000 description 1
• 108010043324 Amyloid Precursor Protein Secretases Proteins 0.000 description 1
• 102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 description 1
• 206010059245 Angiopathy Diseases 0.000 description 1
• 239000004475 Arginine Chemical class 0.000 description 1
• XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
• XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 1
• 229930003347 Atropine Natural products 0.000 description 1
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 1
• 206010003805 Autism Diseases 0.000 description 1
• 208000020706 Autistic disease Diseases 0.000 description 1
• XEAOPVUAMONVLA-QGZVFWFLSA-N Avagacestat Chemical compound C=1C=C(Cl)C=CC=1S(=O)(=O)N([C@H](CCC(F)(F)F)C(=O)N)CC(C(=C1)F)=CC=C1C=1N=CON=1 XEAOPVUAMONVLA-QGZVFWFLSA-N 0.000 description 1
• CKWAABXVOKTZGV-UHFFFAOYSA-N B(O)O.CN(C=O)C Chemical compound B(O)O.CN(C=O)C CKWAABXVOKTZGV-UHFFFAOYSA-N 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• 102100021257 Beta-secretase 1 Human genes 0.000 description 1
• 241000283690 Bos taurus Species 0.000 description 1
• 208000002381 Brain Hypoxia Diseases 0.000 description 1
• 206010048962 Brain oedema Diseases 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
• CLGWUCNXOBLWFM-UHFFFAOYSA-N CZC-25146 Chemical compound COC1=CC(N2CCOCC2)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1NS(C)(=O)=O CLGWUCNXOBLWFM-UHFFFAOYSA-N 0.000 description 1
• WZLSMINROHSYAA-LBPRGKRZSA-N C[C@H]1CN(CCO1)C=1C2=C(N=CN1)NC=C2C2=C(C#N)C=CC=C2 Chemical compound C[C@H]1CN(CCO1)C=1C2=C(N=CN1)NC=C2C2=C(C#N)C=CC=C2 WZLSMINROHSYAA-LBPRGKRZSA-N 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• 229940127291 Calcium channel antagonist Drugs 0.000 description 1
• 241000282472 Canis lupus familiaris Species 0.000 description 1
• 241000283707 Capra Species 0.000 description 1
• OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
• 206010065559 Cerebral arteriosclerosis Diseases 0.000 description 1
• 206010008111 Cerebral haemorrhage Diseases 0.000 description 1
• 108091006146 Channels Proteins 0.000 description 1
• 229920001661 Chitosan Polymers 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• 208000019888 Circadian rhythm sleep disease Diseases 0.000 description 1
• QCDFBFJGMNKBDO-UHFFFAOYSA-N Clioquinol Chemical compound C1=CN=C2C(O)=C(I)C=C(Cl)C2=C1 QCDFBFJGMNKBDO-UHFFFAOYSA-N 0.000 description 1
• 208000022497 Cocaine-Related disease Diseases 0.000 description 1
• 102000008186 Collagen Human genes 0.000 description 1
• 108010035532 Collagen Proteins 0.000 description 1
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
• 229920000742 Cotton Polymers 0.000 description 1
• 208000020406 Creutzfeldt Jacob disease Diseases 0.000 description 1
• 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 description 1
• 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 description 1
• 229920000858 Cyclodextrin Polymers 0.000 description 1
• 102000004127 Cytokines Human genes 0.000 description 1
• 108090000695 Cytokines Proteins 0.000 description 1
• 229930182843 D-Lactic acid Natural products 0.000 description 1
• RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
• RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
• AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 1
• JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 description 1
• 206010011878 Deafness Diseases 0.000 description 1
• 206010012218 Delirium Diseases 0.000 description 1
• 208000024254 Delusional disease Diseases 0.000 description 1
• 208000020401 Depressive disease Diseases 0.000 description 1
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
• 239000012848 Dextrorphan Substances 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
• 208000007590 Disorders of Excessive Somnolence Diseases 0.000 description 1
• 208000026331 Disruptive, Impulse Control, and Conduct disease Diseases 0.000 description 1
• 201000010374 Down Syndrome Diseases 0.000 description 1
• 206010013754 Drug withdrawal syndrome Diseases 0.000 description 1
• 208000012661 Dyskinesia Diseases 0.000 description 1
• 208000014094 Dystonic disease Diseases 0.000 description 1
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
• 241000283086 Equidae Species 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• 102100020903 Ezrin Human genes 0.000 description 1
• 241000282326 Felis catus Species 0.000 description 1
• 206010016654 Fibrosis Diseases 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• 208000010235 Food Addiction Diseases 0.000 description 1
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
• 208000001914 Fragile X syndrome Diseases 0.000 description 1
• 201000011240 Frontotemporal dementia Diseases 0.000 description 1
• 108091006109 GTPases Proteins 0.000 description 1
• 208000001613 Gambling Diseases 0.000 description 1
• 229920002148 Gellan gum Polymers 0.000 description 1
• 208000011688 Generalised anxiety disease Diseases 0.000 description 1
• 201000004311 Gilles de la Tourette syndrome Diseases 0.000 description 1
• 239000009429 Ginkgo biloba extract Substances 0.000 description 1
• 102000018899 Glutamate Receptors Human genes 0.000 description 1
• 108010027915 Glutamate Receptors Proteins 0.000 description 1
• 239000004471 Glycine Chemical class 0.000 description 1
• 102000010726 Glycine Plasma Membrane Transport Proteins Human genes 0.000 description 1
• 108010063380 Glycine Plasma Membrane Transport Proteins Proteins 0.000 description 1
• AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
• 208000031886 HIV Infections Diseases 0.000 description 1
• 102000006354 HLA-DR Antigens Human genes 0.000 description 1
• 108010058597 HLA-DR Antigens Proteins 0.000 description 1
• RERZNCLIYCABFS-UHFFFAOYSA-N Harmaline hydrochloride Natural products C1CN=C(C)C2=C1C1=CC=C(OC)C=C1N2 RERZNCLIYCABFS-UHFFFAOYSA-N 0.000 description 1
• 101000894895 Homo sapiens Beta-secretase 1 Proteins 0.000 description 1
• 208000023105 Huntington disease Diseases 0.000 description 1
• ZRJBHWIHUMBLCN-SEQYCRGISA-N Huperzine A Natural products N1C(=O)C=CC2=C1C[C@H]1/C(=C/C)[C@]2(N)CC(C)=C1 ZRJBHWIHUMBLCN-SEQYCRGISA-N 0.000 description 1
• 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
• 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
• STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 1
• 238000004566 IR spectroscopy Methods 0.000 description 1
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
• 208000030990 Impulse-control disease Diseases 0.000 description 1
• 102000004877 Insulin Human genes 0.000 description 1
• 108090001061 Insulin Proteins 0.000 description 1
• 102100021496 Insulin-degrading enzyme Human genes 0.000 description 1
• 108090000828 Insulysin Proteins 0.000 description 1
• 102000014150 Interferons Human genes 0.000 description 1
• 108010050904 Interferons Proteins 0.000 description 1
• 229930194542 Keto Natural products 0.000 description 1
• 238000005577 Kumada cross-coupling reaction Methods 0.000 description 1
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical class NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
• SNDPXSYFESPGGJ-UHFFFAOYSA-N L-norVal-OH Natural products CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 description 1
• MKXZASYAUGDDCJ-SZMVWBNQSA-N LSM-2525 Chemical compound C1CCC[C@H]2[C@@]3([H])N(C)CC[C@]21C1=CC(OC)=CC=C1C3 MKXZASYAUGDDCJ-SZMVWBNQSA-N 0.000 description 1
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
• 108010020246 Leucine-Rich Repeat Serine-Threonine Protein Kinase-2 Proteins 0.000 description 1
• 102000009784 Leucine-Rich Repeat Serine-Threonine Protein Kinase-2 Human genes 0.000 description 1
• 102220577984 Leucine-rich repeat serine/threonine-protein kinase 2_I2020T_mutation Human genes 0.000 description 1
• 102220578195 Leucine-rich repeat serine/threonine-protein kinase 2_M2397T_mutation Human genes 0.000 description 1
• 102220596654 Leucine-rich repeat serine/threonine-protein kinase 2_R1441C_mutation Human genes 0.000 description 1
• 102220596659 Leucine-rich repeat serine/threonine-protein kinase 2_R1441H_mutation Human genes 0.000 description 1
• 102220577884 Leucine-rich repeat serine/threonine-protein kinase 2_Y1699C_mutation Human genes 0.000 description 1
• JAQUASYNZVUNQP-USXIJHARSA-N Levorphanol Chemical compound C1C2=CC=C(O)C=C2[C@]23CCN(C)[C@H]1[C@@H]2CCCC3 JAQUASYNZVUNQP-USXIJHARSA-N 0.000 description 1
• 208000009829 Lewy Body Disease Diseases 0.000 description 1
• 201000002832 Lewy body dementia Diseases 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
• 239000004472 Lysine Chemical class 0.000 description 1
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Chemical class NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
• 208000036626 Mental retardation Diseases 0.000 description 1
• FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 1
• 102000016193 Metabotropic glutamate receptors Human genes 0.000 description 1
• 108010010914 Metabotropic glutamate receptors Proteins 0.000 description 1
• UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
• PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 1
• 208000016285 Movement disease Diseases 0.000 description 1
• 241000699666 Mus <mouse, genus> Species 0.000 description 1
• 241000699660 Mus musculus Species 0.000 description 1
• 241000699670 Mus sp. Species 0.000 description 1
• 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 1
• 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 1
• 208000010428 Muscle Weakness Diseases 0.000 description 1
• 206010028372 Muscular weakness Diseases 0.000 description 1
• STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 1
• RTHCYVBBDHJXIQ-UHFFFAOYSA-N N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine Chemical compound C=1C=CC=CC=1C(CCNC)OC1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-UHFFFAOYSA-N 0.000 description 1
• CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
• 238000006411 Negishi coupling reaction Methods 0.000 description 1
• 208000036110 Neuroinflammatory disease Diseases 0.000 description 1
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
• 206010057852 Nicotine dependence Diseases 0.000 description 1
• 229940123925 Nicotinic receptor agonist Drugs 0.000 description 1
• 208000010577 Niemann-Pick disease type C Diseases 0.000 description 1
• 102000008299 Nitric Oxide Synthase Human genes 0.000 description 1
• 108010021487 Nitric Oxide Synthase Proteins 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• DITOENWBJBNZSL-UHFFFAOYSA-N O-methyl-hippeastrine Natural products C1=C2C3C4N(C)CCC4=CC(OC)C3OC(=O)C2=CC2=C1OCO2 DITOENWBJBNZSL-UHFFFAOYSA-N 0.000 description 1
• 208000008589 Obesity Diseases 0.000 description 1
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
• FELGMEQIXOGIFQ-UHFFFAOYSA-N Ondansetron Chemical compound CC1=NC=CN1CC1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FELGMEQIXOGIFQ-UHFFFAOYSA-N 0.000 description 1
• 241000283973 Oryctolagus cuniculus Species 0.000 description 1
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
• 229940076380 PDE9 inhibitor Drugs 0.000 description 1
• 206010033701 Papillary thyroid cancer Diseases 0.000 description 1
• AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 description 1
• 241001494479 Pecora Species 0.000 description 1
• 229920002230 Pectic acid Polymers 0.000 description 1
• 229940121836 Phosphodiesterase 1 inhibitor Drugs 0.000 description 1
• 229940121828 Phosphodiesterase 2 inhibitor Drugs 0.000 description 1
• 229940123263 Phosphodiesterase 3 inhibitor Drugs 0.000 description 1
• 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 description 1
• 229940123333 Phosphodiesterase 5 inhibitor Drugs 0.000 description 1
• 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 1
• 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 1
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
• PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 description 1
• 208000000609 Pick Disease of the Brain Diseases 0.000 description 1
• 239000002202 Polyethylene glycol Substances 0.000 description 1
• 239000004372 Polyvinyl alcohol Substances 0.000 description 1
• 201000009916 Postpartum depression Diseases 0.000 description 1
• 241000288906 Primates Species 0.000 description 1
• 102000029797 Prion Human genes 0.000 description 1
• 108091000054 Prion Proteins 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
• XLBIBBZXLMYSFF-UHFFFAOYSA-M Propantheline bromide Chemical compound [Br-].C1=CC=C2C(C(=O)OCC[N+](C)(C(C)C)C(C)C)C3=CC=CC=C3OC2=C1 XLBIBBZXLMYSFF-UHFFFAOYSA-M 0.000 description 1
• 206010060862 Prostate cancer Diseases 0.000 description 1
• 102000001253 Protein Kinase Human genes 0.000 description 1
• 208000028017 Psychotic disease Diseases 0.000 description 1
• LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 1
• 102100022127 Radixin Human genes 0.000 description 1
• 206010038389 Renal cancer Diseases 0.000 description 1
• 208000006265 Renal cell carcinoma Diseases 0.000 description 1
• 206010071390 Resting tremor Diseases 0.000 description 1
• 208000017442 Retinal disease Diseases 0.000 description 1
• 206010038923 Retinopathy Diseases 0.000 description 1
• FTALBRSUTCGOEG-UHFFFAOYSA-N Riluzole Chemical compound C1=C(OC(F)(F)F)C=C2SC(N)=NC2=C1 FTALBRSUTCGOEG-UHFFFAOYSA-N 0.000 description 1
• NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 description 1
• 241000283984 Rodentia Species 0.000 description 1
• RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 1
• 229940124639 Selective inhibitor Drugs 0.000 description 1
• 206010039966 Senile dementia Diseases 0.000 description 1
• 201000001880 Sexual dysfunction Diseases 0.000 description 1
• ZRJBHWIHUMBLCN-UHFFFAOYSA-N Shuangyiping Natural products N1C(=O)C=CC2=C1CC1C(=CC)C2(N)CC(C)=C1 ZRJBHWIHUMBLCN-UHFFFAOYSA-N 0.000 description 1
• 208000000453 Skin Neoplasms Diseases 0.000 description 1
• 208000010340 Sleep Deprivation Diseases 0.000 description 1
• 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
• 206010041250 Social phobia Diseases 0.000 description 1
• 229920002125 Sokalan® Polymers 0.000 description 1
• 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• 241000282887 Suidae Species 0.000 description 1
• ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
• 208000009205 Tinnitus Diseases 0.000 description 1
• 208000025569 Tobacco Use disease Diseases 0.000 description 1
• 208000000323 Tourette Syndrome Diseases 0.000 description 1
• 208000016620 Tourette disease Diseases 0.000 description 1
• 208000031674 Traumatic Acute Stress disease Diseases 0.000 description 1
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
• 239000007983 Tris buffer Substances 0.000 description 1
• YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
• 208000007930 Type C Niemann-Pick Disease Diseases 0.000 description 1
• 206010046543 Urinary incontinence Diseases 0.000 description 1
• 201000004810 Vascular dementia Diseases 0.000 description 1
• 102000013814 Wnt Human genes 0.000 description 1
• 108050003627 Wnt Proteins 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• JGAGHIIOCADQOV-CTNGQTDRSA-N [(3ar,8bs)-3,4,8b-trimethyl-2,3a-dihydro-1h-pyrrolo[2,3-b]indol-7-yl] n-(2-methylphenyl)carbamate Chemical compound CN([C@@H]1[C@@](C2=C3)(C)CCN1C)C2=CC=C3OC(=O)NC1=CC=CC=C1C JGAGHIIOCADQOV-CTNGQTDRSA-N 0.000 description 1
• PBHFNBQPZCRWQP-QUCCMNQESA-N [(3ar,8bs)-3,4,8b-trimethyl-2,3a-dihydro-1h-pyrrolo[2,3-b]indol-7-yl] n-phenylcarbamate Chemical compound CN([C@@H]1[C@@](C2=C3)(C)CCN1C)C2=CC=C3OC(=O)NC1=CC=CC=C1 PBHFNBQPZCRWQP-QUCCMNQESA-N 0.000 description 1
• YYBNDIVPHIWTPK-KYJQVDHRSA-N [(3as,8bs)-3,4,8b-trimethyl-1,2,3,3a-tetrahydropyrrolo[2,3-b]indol-3-ium-7-yl] n-methylcarbamate;sulfate Chemical compound [O-]S([O-])(=O)=O.C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CC[NH+]2C.C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CC[NH+]2C YYBNDIVPHIWTPK-KYJQVDHRSA-N 0.000 description 1
• ZOBDWFRKFSPCRB-UNMCSNQZSA-N [(4as,9as)-2,4a,9-trimethyl-4,9a-dihydro-3h-oxazino[6,5-b]indol-6-yl] n-(2-ethylphenyl)carbamate Chemical compound CCC1=CC=CC=C1NC(=O)OC1=CC=C(N(C)[C@@H]2[C@@]3(C)CCN(C)O2)C3=C1 ZOBDWFRKFSPCRB-UNMCSNQZSA-N 0.000 description 1
• CLTLWPSRLYCESA-UHFFFAOYSA-N [1-(5-phenyl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-yl]methanol Chemical compound C1CC(CO)CCN1C1=NC=NC2=C1C(C=1C=CC=CC=1)=CN2 CLTLWPSRLYCESA-UHFFFAOYSA-N 0.000 description 1
• WBJOXEMWHITGBW-UHFFFAOYSA-N [4-[5-(1-methylpyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholin-2-yl]methanol Chemical compound C1=NN(C)C=C1C1=CNC2=NC=NC(N3CC(CO)OCC3)=C12 WBJOXEMWHITGBW-UHFFFAOYSA-N 0.000 description 1
• 230000002159 abnormal effect Effects 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• AFCGFAGUEYAMAO-UHFFFAOYSA-N acamprosate Chemical compound CC(=O)NCCCS(O)(=O)=O AFCGFAGUEYAMAO-UHFFFAOYSA-N 0.000 description 1
• 229960004047 acamprosate Drugs 0.000 description 1
• 238000009825 accumulation Methods 0.000 description 1
• IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 230000001154 acute effect Effects 0.000 description 1
• 208000026345 acute stress disease Diseases 0.000 description 1
• WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
• 238000009098 adjuvant therapy Methods 0.000 description 1
• 239000000695 adrenergic alpha-agonist Substances 0.000 description 1
• 229940013181 advil Drugs 0.000 description 1
• 230000032683 aging Effects 0.000 description 1
• 238000013019 agitation Methods 0.000 description 1
• 239000000556 agonist Substances 0.000 description 1
• 201000007930 alcohol dependence Diseases 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 229940060515 aleve Drugs 0.000 description 1
• 229940072056 alginate Drugs 0.000 description 1
• 235000010443 alginic acid Nutrition 0.000 description 1
• 229920000615 alginic acid Polymers 0.000 description 1
• 125000001931 aliphatic group Chemical group 0.000 description 1
• 229910052783 alkali metal Inorganic materials 0.000 description 1
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
• 125000003545 alkoxy group Chemical group 0.000 description 1
• 150000001347 alkyl bromides Chemical class 0.000 description 1
• 150000001350 alkyl halides Chemical class 0.000 description 1
• AEMOLEFTQBMNLQ-BKBMJHBISA-N alpha-D-galacturonic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-BKBMJHBISA-N 0.000 description 1
• AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
• CJCSPKMFHVPWAR-JTQLQIEISA-N alpha-methyl-L-dopa Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 CJCSPKMFHVPWAR-JTQLQIEISA-N 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 230000007791 alzheimer disease like pathology Effects 0.000 description 1
• 229960000836 amitriptyline Drugs 0.000 description 1
• 230000006986 amnesia Effects 0.000 description 1
• 229940025141 anafranil Drugs 0.000 description 1
• 239000002269 analeptic agent Substances 0.000 description 1
• 229940072359 anaprox Drugs 0.000 description 1
• 150000001450 anions Chemical class 0.000 description 1
• 208000022531 anorexia Diseases 0.000 description 1
• 229940089918 ansaid Drugs 0.000 description 1
• 239000005557 antagonist Substances 0.000 description 1
• 230000001773 anti-convulsant effect Effects 0.000 description 1
• 239000001961 anticonvulsive agent Substances 0.000 description 1
• 229960003965 antiepileptics Drugs 0.000 description 1
• 239000000164 antipsychotic agent Substances 0.000 description 1
• 230000006907 apoptotic process Effects 0.000 description 1
• BFNCJMURTMZBTE-UHFFFAOYSA-N aptiganel Chemical compound CCC1=CC=CC(N(C)C(N)=NC=2C3=CC=CC=C3C=CC=2)=C1 BFNCJMURTMZBTE-UHFFFAOYSA-N 0.000 description 1
• 229950001180 aptiganel Drugs 0.000 description 1
• 229960003121 arginine Drugs 0.000 description 1
• 229910052786 argon Inorganic materials 0.000 description 1
• 229940039856 aricept Drugs 0.000 description 1
• 150000001502 aryl halides Chemical class 0.000 description 1
• 229940072107 ascorbate Drugs 0.000 description 1
• 235000010323 ascorbic acid Nutrition 0.000 description 1
• 239000011668 ascorbic acid Substances 0.000 description 1
• 229940009098 aspartate Drugs 0.000 description 1
• 239000012298 atmosphere Substances 0.000 description 1
• 229960005370 atorvastatin Drugs 0.000 description 1
• FQCKMBLVYCEXJB-MNSAWQCASA-L atorvastatin calcium Chemical compound [Ca+2].C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC([O-])=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1.C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC([O-])=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 FQCKMBLVYCEXJB-MNSAWQCASA-L 0.000 description 1
• 229940022802 atropen Drugs 0.000 description 1
• 229960000396 atropine Drugs 0.000 description 1
• 230000002238 attenuated effect Effects 0.000 description 1
• 230000004900 autophagic degradation Effects 0.000 description 1
• PCCNIENXBRUYFK-UHFFFAOYSA-O azanium;cerium(4+);pentanitrate Chemical compound [NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PCCNIENXBRUYFK-UHFFFAOYSA-O 0.000 description 1
• 125000002785 azepinyl group Chemical group 0.000 description 1
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 description 1
• 125000002393 azetidinyl group Chemical group 0.000 description 1
• 229940031774 azilect Drugs 0.000 description 1
• 229950001863 bapineuzumab Drugs 0.000 description 1
• 230000004888 barrier function Effects 0.000 description 1
• IALVDLPLCLFBCF-CHWSQXEVSA-N befloxatone Chemical compound O=C1O[C@@H](COC)CN1C1=CC=C(OCC[C@@H](O)C(F)(F)F)C=C1 IALVDLPLCLFBCF-CHWSQXEVSA-N 0.000 description 1
• 229950000017 befloxatone Drugs 0.000 description 1
• 230000006399 behavior Effects 0.000 description 1
• 230000003542 behavioural effect Effects 0.000 description 1
• 229940088007 benadryl Drugs 0.000 description 1
• BNQDCRGUHNALGH-UHFFFAOYSA-N benserazide Chemical compound OCC(N)C(=O)NNCC1=CC=C(O)C(O)=C1O BNQDCRGUHNALGH-UHFFFAOYSA-N 0.000 description 1
• 229960000911 benserazide Drugs 0.000 description 1
• 229940090012 bentyl Drugs 0.000 description 1
• 229960000686 benzalkonium chloride Drugs 0.000 description 1
• 229960001081 benzatropine Drugs 0.000 description 1
• GIJXKZJWITVLHI-PMOLBWCYSA-N benzatropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(C=1C=CC=CC=1)C1=CC=CC=C1 GIJXKZJWITVLHI-PMOLBWCYSA-N 0.000 description 1
• 229940077388 benzenesulfonate Drugs 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
• 229940092714 benzenesulfonic acid Drugs 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 125000005605 benzo group Chemical group 0.000 description 1
• BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
• 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004600 benzothiopyranyl group Chemical group S1C(C=CC2=C1C=CC=C2)* 0.000 description 1
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
• 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 1
• 229940024774 benztropine mesylate Drugs 0.000 description 1
• HDYQLGLEPPGPEV-UHFFFAOYSA-N benzyl 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)OCC1=CC=CC=C1 HDYQLGLEPPGPEV-UHFFFAOYSA-N 0.000 description 1
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
• CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
• 102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
• 108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
• 239000002876 beta blocker Substances 0.000 description 1
• 229940097320 beta blocking agent Drugs 0.000 description 1
• XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
• 229950010365 bicifadine Drugs 0.000 description 1
• OFYVIGTWSQPCLF-NWDGAFQWSA-N bicifadine Chemical compound C1=CC(C)=CC=C1[C@@]1(CNC2)[C@H]2C1 OFYVIGTWSQPCLF-NWDGAFQWSA-N 0.000 description 1
• 239000000227 bioadhesive Substances 0.000 description 1
• 238000004166 bioassay Methods 0.000 description 1
• 208000028683 bipolar I disease Diseases 0.000 description 1
• 208000022257 bipolar II disease Diseases 0.000 description 1
• 230000008499 blood brain barrier function Effects 0.000 description 1
• 210000001218 blood-brain barrier Anatomy 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
• 239000004327 boric acid Substances 0.000 description 1
• 125000005620 boronic acid group Chemical group 0.000 description 1
• 208000006752 brain edema Diseases 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 239000000480 calcium channel blocker Substances 0.000 description 1
• 159000000007 calcium salts Chemical class 0.000 description 1
• 201000011510 cancer Diseases 0.000 description 1
• 125000002837 carbocyclic group Chemical group 0.000 description 1
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
• KPWSJANDNDDRMB-QAQDUYKDSA-N cariprazine Chemical compound C1C[C@@H](NC(=O)N(C)C)CC[C@@H]1CCN1CCN(C=2C(=C(Cl)C=CC=2)Cl)CC1 KPWSJANDNDDRMB-QAQDUYKDSA-N 0.000 description 1
• 229960005123 cariprazine Drugs 0.000 description 1
• 239000012876 carrier material Substances 0.000 description 1
• 150000001768 cations Chemical class 0.000 description 1
• RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 description 1
• 229960000590 celecoxib Drugs 0.000 description 1
• 229940047493 celexa Drugs 0.000 description 1
• 210000004027 cell Anatomy 0.000 description 1
• 230000030833 cell death Effects 0.000 description 1
• 230000033077 cellular process Effects 0.000 description 1
• 210000003169 central nervous system Anatomy 0.000 description 1
• 238000012512 characterization method Methods 0.000 description 1
• FFPXPXOAFQCNBS-MRVPVSSYSA-N chembl1513993 Chemical compound N1=CC=2C(=O)NC(C[C@@H](C)C(F)(F)F)=NC=2N1C1=CC=CC=C1Cl FFPXPXOAFQCNBS-MRVPVSSYSA-N 0.000 description 1
• RVEJWGYZBXCGGM-DNVCBOLYSA-N chembl2179094 Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)C)N1CC1=CC=CC=C1 RVEJWGYZBXCGGM-DNVCBOLYSA-N 0.000 description 1
• 239000007810 chemical reaction solvent Substances 0.000 description 1
• 239000012320 chlorinating reagent Substances 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 1
• 229960002023 chloroprocaine Drugs 0.000 description 1
• 239000000544 cholinesterase inhibitor Substances 0.000 description 1
• 229960001653 citalopram Drugs 0.000 description 1
• 238000003776 cleavage reaction Methods 0.000 description 1
• 229960005228 clioquinol Drugs 0.000 description 1
• 229960004606 clomipramine Drugs 0.000 description 1
• 230000002566 clonic effect Effects 0.000 description 1
• 201000006145 cocaine dependence Diseases 0.000 description 1
• 229940110456 cocoa butter Drugs 0.000 description 1
• 235000019868 cocoa butter Nutrition 0.000 description 1
• 229940097480 cogentin Drugs 0.000 description 1
• 230000001149 cognitive effect Effects 0.000 description 1
• 206010009887 colitis Diseases 0.000 description 1
• 229920001436 collagen Polymers 0.000 description 1
• 108010002212 colostrinine Proteins 0.000 description 1
• 238000013270 controlled release Methods 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 229910052802 copper Inorganic materials 0.000 description 1
• 239000010949 copper Substances 0.000 description 1
• 239000003246 corticosteroid Substances 0.000 description 1
• 229960001334 corticosteroids Drugs 0.000 description 1
• 239000012043 crude product Substances 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 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 1
• HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 229940029644 cymbalta Drugs 0.000 description 1
• 230000003436 cytoskeletal effect Effects 0.000 description 1
• 229940022769 d- lactic acid Drugs 0.000 description 1
• 206010061428 decreased appetite Diseases 0.000 description 1
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 230000002950 deficient Effects 0.000 description 1
• 239000007933 dermal patch Substances 0.000 description 1
• 238000013461 design Methods 0.000 description 1
• 229960003914 desipramine Drugs 0.000 description 1
• 229960001623 desvenlafaxine Drugs 0.000 description 1
• 238000001514 detection method Methods 0.000 description 1
• 229940076405 detrol Drugs 0.000 description 1
• 239000011903 deuterated solvents‎ Substances 0.000 description 1
• 229910052805 deuterium Inorganic materials 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• 230000018109 developmental process Effects 0.000 description 1
• SSQJFGMEZBFMNV-PMACEKPBSA-N dexanabinol Chemical compound C1C(CO)=CC[C@@H]2C(C)(C)OC3=CC(C(C)(C)CCCCCC)=CC(O)=C3[C@H]21 SSQJFGMEZBFMNV-PMACEKPBSA-N 0.000 description 1
• 229960001985 dextromethorphan Drugs 0.000 description 1
• JAQUASYNZVUNQP-PVAVHDDUSA-N dextrorphan Chemical compound C1C2=CC=C(O)C=C2[C@@]23CCN(C)[C@@H]1[C@H]2CCCC3 JAQUASYNZVUNQP-PVAVHDDUSA-N 0.000 description 1
• 229950006878 dextrorphan Drugs 0.000 description 1
• PBGGNZZGJIKBMJ-UHFFFAOYSA-N di(propan-2-yl)azanide Chemical compound CC(C)[N-]C(C)C PBGGNZZGJIKBMJ-UHFFFAOYSA-N 0.000 description 1
• 150000008050 dialkyl sulfates Chemical class 0.000 description 1
• 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 description 1
• KXZOIWWTXOCYKR-UHFFFAOYSA-M diclofenac potassium Chemical compound [K+].[O-]C(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl KXZOIWWTXOCYKR-UHFFFAOYSA-M 0.000 description 1
• 229960004515 diclofenac potassium Drugs 0.000 description 1
• 229960001193 diclofenac sodium Drugs 0.000 description 1
• KPHWPUGNDIVLNH-UHFFFAOYSA-M diclofenac sodium Chemical compound [Na+].[O-]C(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl KPHWPUGNDIVLNH-UHFFFAOYSA-M 0.000 description 1
• CURUTKGFNZGFSE-UHFFFAOYSA-N dicyclomine Chemical compound C1CCCCC1C1(C(=O)OCCN(CC)CC)CCCCC1 CURUTKGFNZGFSE-UHFFFAOYSA-N 0.000 description 1
• 229940043237 diethanolamine Drugs 0.000 description 1
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
• CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 1
• 229960000616 diflunisal Drugs 0.000 description 1
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
• 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
• 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
• 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 description 1
• 238000007865 diluting Methods 0.000 description 1
• 239000003085 diluting agent Substances 0.000 description 1
• VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
• 229950010286 diolamine Drugs 0.000 description 1
• 229960000520 diphenhydramine Drugs 0.000 description 1
• DKGJFKPIUSHDIT-UHFFFAOYSA-L disodium;propane-1,3-disulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)CCCS([O-])(=O)=O DKGJFKPIUSHDIT-UHFFFAOYSA-L 0.000 description 1
• 229940099170 ditropan Drugs 0.000 description 1
• LBOJYSIDWZQNJS-CVEARBPZSA-N dizocilpine Chemical compound C12=CC=CC=C2[C@]2(C)C3=CC=CC=C3C[C@H]1N2 LBOJYSIDWZQNJS-CVEARBPZSA-N 0.000 description 1
• 229950004794 dizocilpine Drugs 0.000 description 1
• 229940048879 dl tartaric acid Drugs 0.000 description 1
• 229940110377 dl- arginine Drugs 0.000 description 1
• 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
• 229940043264 dodecyl sulfate Drugs 0.000 description 1
• 229940072701 dolobid Drugs 0.000 description 1
• 229940072340 dolophine Drugs 0.000 description 1
• ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Natural products O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 description 1
• 229960003135 donepezil hydrochloride Drugs 0.000 description 1
• 229960003638 dopamine Drugs 0.000 description 1
• 239000003210 dopamine receptor blocking agent Substances 0.000 description 1
• 239000003136 dopamine receptor stimulating agent Substances 0.000 description 1
• 239000000221 dopamine uptake inhibitor Substances 0.000 description 1
• 210000005064 dopaminergic neuron Anatomy 0.000 description 1
• ODQWQRRAPPTVAG-UHFFFAOYSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 ODQWQRRAPPTVAG-UHFFFAOYSA-N 0.000 description 1
• 229960005426 doxepin Drugs 0.000 description 1
• 239000013583 drug formulation Substances 0.000 description 1
• 229940112141 dry powder inhaler Drugs 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 229960002866 duloxetine Drugs 0.000 description 1
• 238000010410 dusting Methods 0.000 description 1
• 230000004064 dysfunction Effects 0.000 description 1
• 208000010118 dystonia Diseases 0.000 description 1
• 229940098766 effexor Drugs 0.000 description 1
• 229940011681 elavil Drugs 0.000 description 1
• 229940084238 eldepryl Drugs 0.000 description 1
• 229950005627 embonate Drugs 0.000 description 1
• 229940071670 emsam Drugs 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 238000003821 enantio-separation Methods 0.000 description 1
• 238000005516 engineering process Methods 0.000 description 1
• 150000002085 enols Chemical class 0.000 description 1
• HKSZLNNOFSGOKW-UHFFFAOYSA-N ent-staurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(C)O1 HKSZLNNOFSGOKW-UHFFFAOYSA-N 0.000 description 1
• 239000002702 enteric coating Substances 0.000 description 1
• 238000009505 enteric coating Methods 0.000 description 1
• 229950004685 eprodisate Drugs 0.000 description 1
• WSEQXVZVJXJVFP-FQEVSTJZSA-N escitalopram Chemical compound C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-FQEVSTJZSA-N 0.000 description 1
• 229960004341 escitalopram Drugs 0.000 description 1
• 150000002148 esters Chemical class 0.000 description 1
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
• 125000004494 ethyl ester group Chemical group 0.000 description 1
• PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
• SFNALCNOMXIBKG-UHFFFAOYSA-N ethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCO SFNALCNOMXIBKG-UHFFFAOYSA-N 0.000 description 1
• 229940012017 ethylenediamine Drugs 0.000 description 1
• 230000005284 excitation Effects 0.000 description 1
• 229940108366 exelon Drugs 0.000 description 1
• 230000001747 exhibiting effect Effects 0.000 description 1
• 239000000284 extract Substances 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 231100000040 eye damage Toxicity 0.000 description 1
• 239000003889 eye drop Substances 0.000 description 1
• 229940012356 eye drops Drugs 0.000 description 1
• 108010055671 ezrin Proteins 0.000 description 1
• 230000002349 favourable effect Effects 0.000 description 1
• 229960001582 fenfluramine Drugs 0.000 description 1
• 229960001419 fenoprofen Drugs 0.000 description 1
• 239000000835 fiber Substances 0.000 description 1
• 230000004761 fibrosis Effects 0.000 description 1
• 239000010408 film Substances 0.000 description 1
• 239000012065 filter cake Substances 0.000 description 1
• GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
• 229910052731 fluorine Inorganic materials 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 229960002464 fluoxetine Drugs 0.000 description 1
• 229960002390 flurbiprofen Drugs 0.000 description 1
• 229960004038 fluvoxamine Drugs 0.000 description 1
• CJOFXWAVKWHTFT-XSFVSMFZSA-N fluvoxamine Chemical compound COCCCC\C(=N/OCCN)C1=CC=C(C(F)(F)F)C=C1 CJOFXWAVKWHTFT-XSFVSMFZSA-N 0.000 description 1
• 239000006260 foam Substances 0.000 description 1
• 235000003599 food sweetener Nutrition 0.000 description 1
• WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
• 239000012458 free base Substances 0.000 description 1
• 238000007710 freezing Methods 0.000 description 1
• 230000008014 freezing Effects 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 125000000524 functional group Chemical group 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 1
• 229960002024 galantamine hydrobromide Drugs 0.000 description 1
• 229950000264 ganstigmine Drugs 0.000 description 1
• 229950002508 gantenerumab Drugs 0.000 description 1
• 239000000216 gellan gum Substances 0.000 description 1
• 235000010492 gellan gum Nutrition 0.000 description 1
• 208000029364 generalized anxiety disease Diseases 0.000 description 1
• 230000002068 genetic effect Effects 0.000 description 1
• 229940068052 ginkgo biloba extract Drugs 0.000 description 1
• 235000020686 ginkgo biloba extract Nutrition 0.000 description 1
• 229940050410 gluconate Drugs 0.000 description 1
• 239000000174 gluconic acid Substances 0.000 description 1
• 235000012208 gluconic acid Nutrition 0.000 description 1
• 229940097042 glucuronate Drugs 0.000 description 1
• 229930195712 glutamate Natural products 0.000 description 1
• 230000036252 glycation Effects 0.000 description 1
• 235000011187 glycerol Nutrition 0.000 description 1
• 229960002449 glycine Drugs 0.000 description 1
• 229940015042 glycopyrrolate Drugs 0.000 description 1
• 150000004820 halides Chemical class 0.000 description 1
• 230000003400 hallucinatory effect Effects 0.000 description 1
• 230000002140 halogenating effect Effects 0.000 description 1
• 239000007902 hard capsule Substances 0.000 description 1
• VJHLDRVYTQNASM-UHFFFAOYSA-N harmine Natural products CC1=CN=CC=2NC3=CC(=CC=C3C=21)OC VJHLDRVYTQNASM-UHFFFAOYSA-N 0.000 description 1
• 210000002216 heart Anatomy 0.000 description 1
• MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
• 125000005553 heteroaryloxy group Chemical group 0.000 description 1
• FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 238000004128 high performance liquid chromatography Methods 0.000 description 1
• 229960001340 histamine Drugs 0.000 description 1
• 230000013632 homeostatic process Effects 0.000 description 1
• ZRJBHWIHUMBLCN-YQEJDHNASA-N huperzine A Chemical compound N1C(=O)C=CC2=C1C[C@H]1\C(=C/C)[C@]2(N)CC(C)=C1 ZRJBHWIHUMBLCN-YQEJDHNASA-N 0.000 description 1
• 229920002674 hyaluronan Polymers 0.000 description 1
• 229960003160 hyaluronic acid Drugs 0.000 description 1
• 150000004677 hydrates Chemical class 0.000 description 1
• 239000000017 hydrogel Substances 0.000 description 1
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
• ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• ZUFVXZVXEJHHBN-UHFFFAOYSA-N hydron;1,2,3,4-tetrahydroacridin-9-amine;chloride Chemical compound [Cl-].C1=CC=C2C([NH3+])=C(CCCC3)C3=NC2=C1 ZUFVXZVXEJHHBN-UHFFFAOYSA-N 0.000 description 1
• 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
• 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
• 229930005342 hyoscyamine Natural products 0.000 description 1
• 229960003210 hyoscyamine Drugs 0.000 description 1
• 206010020765 hypersomnia Diseases 0.000 description 1
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 1
• 125000002632 imidazolidinyl group Chemical group 0.000 description 1
• 125000002636 imidazolinyl group Chemical group 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 125000001841 imino group Chemical group [H]N=* 0.000 description 1
• 229960004801 imipramine Drugs 0.000 description 1
• BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
• 229960002102 imipramine hydrochloride Drugs 0.000 description 1
• 230000028993 immune response Effects 0.000 description 1
• 210000000987 immune system Anatomy 0.000 description 1
• 208000026278 immune system disease Diseases 0.000 description 1
• 229960003444 immunosuppressant agent Drugs 0.000 description 1
• 239000003018 immunosuppressive agent Substances 0.000 description 1
• 238000001727 in vivo Methods 0.000 description 1
• 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 description 1
• 238000011534 incubation Methods 0.000 description 1
• 229940089536 indocin Drugs 0.000 description 1
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
• 229960000905 indomethacin Drugs 0.000 description 1
• 239000003701 inert diluent Substances 0.000 description 1
• 230000002757 inflammatory effect Effects 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 206010022437 insomnia Diseases 0.000 description 1
• 229940125396 insulin Drugs 0.000 description 1
• 230000010354 integration Effects 0.000 description 1
• 229940047124 interferons Drugs 0.000 description 1
• 238000001361 intraarterial administration Methods 0.000 description 1
• 238000007917 intracranial administration Methods 0.000 description 1
• 201000005851 intracranial arteriosclerosis Diseases 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000010255 intramuscular injection Methods 0.000 description 1
• 239000007927 intramuscular injection Substances 0.000 description 1
• 238000007912 intraperitoneal administration Methods 0.000 description 1
• 239000007928 intraperitoneal injection Substances 0.000 description 1
• 238000007913 intrathecal administration Methods 0.000 description 1
• 238000007915 intraurethral administration Methods 0.000 description 1
• 238000010253 intravenous injection Methods 0.000 description 1
• 238000007914 intraventricular administration Methods 0.000 description 1
• 125000002346 iodo group Chemical group I* 0.000 description 1
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
• 150000002500 ions Chemical class 0.000 description 1
• 229950010499 ipenoxazone Drugs 0.000 description 1
• 229940070023 iproniazide Drugs 0.000 description 1
• 208000028867 ischemia Diseases 0.000 description 1
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
• 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
• 125000005990 isobenzothienyl group Chemical group 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 229960002672 isocarboxazid Drugs 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 125000005969 isothiazolinyl group Chemical group 0.000 description 1
• 125000000842 isoxazolyl group Chemical group 0.000 description 1
• 229940039412 ketalar Drugs 0.000 description 1
• 229960003299 ketamine Drugs 0.000 description 1
• 125000000468 ketone group Chemical group 0.000 description 1
• 201000010982 kidney cancer Diseases 0.000 description 1
• 238000000021 kinase assay Methods 0.000 description 1
• 229940043355 kinase inhibitor Drugs 0.000 description 1
• 229940001447 lactate Drugs 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 229940099563 lactobionic acid Drugs 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 229950007396 lecozotan Drugs 0.000 description 1
• 229960003406 levorphanol Drugs 0.000 description 1
• 210000004558 lewy body Anatomy 0.000 description 1
• 229940054157 lexapro Drugs 0.000 description 1
• 239000003446 ligand Substances 0.000 description 1
• 229960003907 linezolid Drugs 0.000 description 1
• 229940002661 lipitor Drugs 0.000 description 1
• 229940057995 liquid paraffin Drugs 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
• GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
• 229960002813 lofepramine Drugs 0.000 description 1
• SAPNXPWPAUFAJU-UHFFFAOYSA-N lofepramine Chemical compound C12=CC=CC=C2CCC2=CC=CC=C2N1CCCN(C)CC(=O)C1=CC=C(Cl)C=C1 SAPNXPWPAUFAJU-UHFFFAOYSA-N 0.000 description 1
• 239000006210 lotion Substances 0.000 description 1
• PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 1
• 229960004844 lovastatin Drugs 0.000 description 1
• QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 1
• 239000007937 lozenge Substances 0.000 description 1
• 201000005202 lung cancer Diseases 0.000 description 1
• 235000018977 lysine Nutrition 0.000 description 1
• 229960003646 lysine Drugs 0.000 description 1
• 208000002780 macular degeneration Diseases 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 159000000003 magnesium salts Chemical class 0.000 description 1
• 230000014759 maintenance of location Effects 0.000 description 1
• 208000024714 major depressive disease Diseases 0.000 description 1
• 229940049920 malate Drugs 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
• 229940110127 marplan Drugs 0.000 description 1
• 238000005259 measurement Methods 0.000 description 1
• 230000001404 mediated effect Effects 0.000 description 1
• 239000012528 membrane Substances 0.000 description 1
• 206010027175 memory impairment Diseases 0.000 description 1
• 230000002503 metabolic effect Effects 0.000 description 1
• 239000002207 metabolite Substances 0.000 description 1
• FJQXCDYVZAHXNS-UHFFFAOYSA-N methadone hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 FJQXCDYVZAHXNS-UHFFFAOYSA-N 0.000 description 1
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• IYETZZCWLLUHIJ-UHFFFAOYSA-N methyl-(1-phenylpropan-2-yl)-prop-2-ynylazanium;chloride Chemical compound Cl.C#CCN(C)C(C)CC1=CC=CC=C1 IYETZZCWLLUHIJ-UHFFFAOYSA-N 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 229950006793 metitepine Drugs 0.000 description 1
• 229960003955 mianserin Drugs 0.000 description 1
• 244000005706 microflora Species 0.000 description 1
• 239000011859 microparticle Substances 0.000 description 1
• 208000027061 mild cognitive impairment Diseases 0.000 description 1
• 229960000600 milnacipran Drugs 0.000 description 1
• 239000002480 mineral oil Substances 0.000 description 1
• 235000010446 mineral oil Nutrition 0.000 description 1
• 239000003595 mist Substances 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 125000002950 monocyclic group Chemical group 0.000 description 1
• 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 description 1
• 125000002757 morpholinyl group Chemical group 0.000 description 1
• 229940072709 motrin Drugs 0.000 description 1
• 210000004877 mucosa Anatomy 0.000 description 1
• 210000003205 muscle Anatomy 0.000 description 1
• 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• FOOIQIOXWVFTPW-UHFFFAOYSA-N n,n-dimethyl-5-(1-methylpyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=2C(N(C)C)=NC=NC=2NC=C1C=1C=NN(C)C=1 FOOIQIOXWVFTPW-UHFFFAOYSA-N 0.000 description 1
• IHLCQCDRRQEAQS-UHFFFAOYSA-N n,n-dimethyl-5-phenyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=2C(N(C)C)=NC=NC=2NC=C1C1=CC=CC=C1 IHLCQCDRRQEAQS-UHFFFAOYSA-N 0.000 description 1
• QXQSUBKWSHMXDP-INIZCTEOSA-N n-[(2s)-5-(6-fluoropyridin-3-yl)-2,3-dihydro-1h-inden-2-yl]propane-2-sulfonamide Chemical compound C([C@@H](CC1=C2)NS(=O)(=O)C(C)C)C1=CC=C2C1=CC=C(F)N=C1 QXQSUBKWSHMXDP-INIZCTEOSA-N 0.000 description 1
• TTYKUKSFWHEBLI-DLBZAZTESA-N n-[(3s,4s)-4-[4-(5-cyanothiophen-2-yl)phenoxy]oxolan-3-yl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)N[C@H]1COC[C@H]1OC1=CC=C(C=2SC(=CC=2)C#N)C=C1 TTYKUKSFWHEBLI-DLBZAZTESA-N 0.000 description 1
• PILCQJJJAFRKHO-UHFFFAOYSA-N n-[1-(5-chloro-2,3-dimethoxyphenyl)ethyl]-2-methylsulfonyl-5-piperazin-1-ylaniline;hydrochloride Chemical compound Cl.COC1=CC(Cl)=CC(C(C)NC=2C(=CC=C(C=2)N2CCNCC2)S(C)(=O)=O)=C1OC PILCQJJJAFRKHO-UHFFFAOYSA-N 0.000 description 1
• AORYJHIFGADLFZ-UHFFFAOYSA-N n-[1-[5-(3-cyanophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]piperidin-4-yl]acetamide Chemical compound C1CC(NC(=O)C)CCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 AORYJHIFGADLFZ-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• GFZZSWWUDZIVCS-UHFFFAOYSA-N n-cyclopropyl-n-methyl-5-(1-methylpyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound N=1C=NC=2NC=C(C3=CN(C)N=C3)C=2C=1N(C)C1CC1 GFZZSWWUDZIVCS-UHFFFAOYSA-N 0.000 description 1
• 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 229940089466 nalfon Drugs 0.000 description 1
• 229940033872 namenda Drugs 0.000 description 1
• KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
• 229940090008 naprosyn Drugs 0.000 description 1
• 229960002009 naproxen Drugs 0.000 description 1
• CDBRNDSHEYLDJV-FVGYRXGTSA-M naproxen sodium Chemical compound [Na+].C1=C([C@H](C)C([O-])=O)C=CC2=CC(OC)=CC=C21 CDBRNDSHEYLDJV-FVGYRXGTSA-M 0.000 description 1
• 229960003940 naproxen sodium Drugs 0.000 description 1
• 229940087524 nardil Drugs 0.000 description 1
• 238000009099 neoadjuvant therapy Methods 0.000 description 1
• OGZQTTHDGQBLBT-UHFFFAOYSA-N neramexane Chemical compound CC1(C)CC(C)(C)CC(C)(N)C1 OGZQTTHDGQBLBT-UHFFFAOYSA-N 0.000 description 1
• 229950004543 neramexane Drugs 0.000 description 1
• 230000003959 neuroinflammation Effects 0.000 description 1
• 230000003961 neuronal insult Effects 0.000 description 1
• 239000004090 neuroprotective agent Substances 0.000 description 1
• 239000000181 nicotinic agonist Substances 0.000 description 1
• 239000002353 niosome Substances 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 150000002825 nitriles Chemical class 0.000 description 1
• DLWSRGHNJVLJAH-UHFFFAOYSA-N nitroflurbiprofen Chemical compound FC1=CC(C(C(=O)OCCCCO[N+]([O-])=O)C)=CC=C1C1=CC=CC=C1 DLWSRGHNJVLJAH-UHFFFAOYSA-N 0.000 description 1
• 229940079063 norflex Drugs 0.000 description 1
• 229940087480 norpramin Drugs 0.000 description 1
• 235000020824 obesity Nutrition 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 239000006186 oral dosage form Substances 0.000 description 1
• 239000013110 organic ligand Substances 0.000 description 1
• 238000006053 organic reaction Methods 0.000 description 1
• 229960003941 orphenadrine Drugs 0.000 description 1
• BHDLTOUYJMTTTM-UHFFFAOYSA-N oxan-3-ol Chemical compound OC1CCCOC1 BHDLTOUYJMTTTM-UHFFFAOYSA-N 0.000 description 1
• URUUZIAJVSGYRC-UHFFFAOYSA-N oxan-3-one Chemical compound O=C1CCCOC1 URUUZIAJVSGYRC-UHFFFAOYSA-N 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 125000003585 oxepinyl group Chemical group 0.000 description 1
• 125000003566 oxetanyl group Chemical group 0.000 description 1
• 125000003544 oxime group Chemical group 0.000 description 1
• 229960005434 oxybutynin Drugs 0.000 description 1
• 125000004430 oxygen atom Chemical group O* 0.000 description 1
• MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
• LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
• PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
• 229940023569 palmate Drugs 0.000 description 1
• 208000019906 panic disease Diseases 0.000 description 1
• 229940014662 pantothenate Drugs 0.000 description 1
• 235000019161 pantothenic acid Nutrition 0.000 description 1
• 239000011713 pantothenic acid Substances 0.000 description 1
• 201000010279 papillary renal cell carcinoma Diseases 0.000 description 1
• 208000002851 paranoid schizophrenia Diseases 0.000 description 1
• 229940026768 parcopa Drugs 0.000 description 1
• 239000006201 parenteral dosage form Substances 0.000 description 1
• 230000036961 partial effect Effects 0.000 description 1
• 239000002245 particle Substances 0.000 description 1
• 230000001717 pathogenic effect Effects 0.000 description 1
• YZPOQCQXOSEMAZ-UHFFFAOYSA-N pbt2 Chemical compound ClC1=CC(Cl)=C(O)C2=NC(CN(C)C)=CC=C21 YZPOQCQXOSEMAZ-UHFFFAOYSA-N 0.000 description 1
• 230000035515 penetration Effects 0.000 description 1
• 235000019371 penicillin G benzathine Nutrition 0.000 description 1
• 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 235000019271 petrolatum Nutrition 0.000 description 1
• 229950010883 phencyclidine Drugs 0.000 description 1
• JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
• 229960000964 phenelzine Drugs 0.000 description 1
• 150000002989 phenols Chemical class 0.000 description 1
• 229940049953 phenylacetate Drugs 0.000 description 1
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
• WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
• 239000002570 phosphodiesterase III inhibitor Substances 0.000 description 1
• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 1
• 239000002590 phosphodiesterase V inhibitor Substances 0.000 description 1
• 150000003904 phospholipids Chemical class 0.000 description 1
• 229910052698 phosphorus Inorganic materials 0.000 description 1
• 239000011574 phosphorus Substances 0.000 description 1
• 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
• 230000000704 physical effect Effects 0.000 description 1
• 229960001697 physostigmine Drugs 0.000 description 1
• PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 description 1
• 229960002516 physostigmine salicylate Drugs 0.000 description 1
• 229960001847 physostigmine sulfate Drugs 0.000 description 1
• 229940075930 picrate Drugs 0.000 description 1
• OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
• 229960002508 pindolol Drugs 0.000 description 1
• 229960005095 pioglitazone Drugs 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 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 description 1
• 229950010765 pivalate Drugs 0.000 description 1
• IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
• 239000004584 polyacrylic acid Substances 0.000 description 1
• 229920001223 polyethylene glycol Polymers 0.000 description 1
• 229920001296 polysiloxane Polymers 0.000 description 1
• 229920002451 polyvinyl alcohol Polymers 0.000 description 1
• 229950003486 ponezumab Drugs 0.000 description 1
• 208000028173 post-traumatic stress disease Diseases 0.000 description 1
• 230000001144 postural effect Effects 0.000 description 1
• 159000000001 potassium salts Chemical class 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• 230000003518 presynaptic effect Effects 0.000 description 1
• 229940014148 pristiq Drugs 0.000 description 1
• 229940099209 probanthine Drugs 0.000 description 1
• MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
• 229960004919 procaine Drugs 0.000 description 1
• 108090000765 processed proteins & peptides Proteins 0.000 description 1
• 230000007425 progressive decline Effects 0.000 description 1
• 230000000750 progressive effect Effects 0.000 description 1
• MGNVWUDMMXZUDI-UHFFFAOYSA-N propane-1,3-disulfonic acid Chemical compound OS(=O)(=O)CCCS(O)(=O)=O MGNVWUDMMXZUDI-UHFFFAOYSA-N 0.000 description 1
• 108060006633 protein kinase Proteins 0.000 description 1
• 235000018102 proteins Nutrition 0.000 description 1
• 102000004169 proteins and genes Human genes 0.000 description 1
• 229940035613 prozac Drugs 0.000 description 1
• SCHKZZSVELPJKU-UHFFFAOYSA-N prx-03140 Chemical compound O=C1N(C(C)C)C=2SC=CC=2C(O)=C1C(=O)NCCCN1CCCCC1 SCHKZZSVELPJKU-UHFFFAOYSA-N 0.000 description 1
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
• 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
• 125000002755 pyrazolinyl group Chemical group 0.000 description 1
• 125000005412 pyrazyl group Chemical group 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical group [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
• OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 description 1
• 230000006824 pyrimidine synthesis Effects 0.000 description 1
• 150000003230 pyrimidines Chemical class 0.000 description 1
• 125000000714 pyrimidinyl group Chemical group 0.000 description 1
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
• 125000001422 pyrrolinyl group Chemical group 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 238000003908 quality control method Methods 0.000 description 1
• 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
• 238000010791 quenching Methods 0.000 description 1
• ZRJBHWIHUMBLCN-BMIGLBTASA-N rac-huperzine A Natural products N1C(=O)C=CC2=C1C[C@@H]1C(=CC)[C@@]2(N)CC(C)=C1 ZRJBHWIHUMBLCN-BMIGLBTASA-N 0.000 description 1
• 230000002285 radioactive effect Effects 0.000 description 1
• 108010048484 radixin Proteins 0.000 description 1
• 229960000245 rasagiline Drugs 0.000 description 1
• 229940051845 razadyne Drugs 0.000 description 1
• 239000000376 reactant Substances 0.000 description 1
• 239000003087 receptor blocking agent Substances 0.000 description 1
• 102000027426 receptor tyrosine kinases Human genes 0.000 description 1
• 108091008598 receptor tyrosine kinases Proteins 0.000 description 1
• 102000005962 receptors Human genes 0.000 description 1
• 108020003175 receptors Proteins 0.000 description 1
• 238000011084 recovery Methods 0.000 description 1
• 230000036454 renin-angiotensin system Effects 0.000 description 1
• 238000011160 research Methods 0.000 description 1
• 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
• 238000012552 review Methods 0.000 description 1
• JUQLTPCYUFPYKE-UHFFFAOYSA-N ritanserin Chemical compound CC=1N=C2SC=CN2C(=O)C=1CCN(CC1)CCC1=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 JUQLTPCYUFPYKE-UHFFFAOYSA-N 0.000 description 1
• 229950009626 ritanserin Drugs 0.000 description 1
• NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 description 1
• 229960000311 ritonavir Drugs 0.000 description 1
• 229960004136 rivastigmine Drugs 0.000 description 1
• 229940106905 robinul Drugs 0.000 description 1
• 102200092172 rs33949390 Human genes 0.000 description 1
• 102220010566 rs74163686 Human genes 0.000 description 1
• NEMGRZFTLSKBAP-LBPRGKRZSA-N safinamide Chemical compound C1=CC(CN[C@@H](C)C(N)=O)=CC=C1OCC1=CC=CC(F)=C1 NEMGRZFTLSKBAP-LBPRGKRZSA-N 0.000 description 1
• 229950002652 safinamide Drugs 0.000 description 1
• YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
• 229960001860 salicylate Drugs 0.000 description 1
• 239000000523 sample Substances 0.000 description 1
• HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
• 230000007017 scission Effects 0.000 description 1
• 229960002646 scopolamine Drugs 0.000 description 1
• CXYRUNPLKGGUJF-RAFJPFSSSA-M scopolamine methobromide Chemical compound [Br-].C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)C)=CC=CC=C1 CXYRUNPLKGGUJF-RAFJPFSSSA-M 0.000 description 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 230000028327 secretion Effects 0.000 description 1
• 229960003678 selegiline hydrochloride Drugs 0.000 description 1
• 238000013207 serial dilution Methods 0.000 description 1
• 229960002073 sertraline Drugs 0.000 description 1
• BLFQGGGGFNSJKA-XHXSRVRCSA-N sertraline hydrochloride Chemical compound Cl.C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 BLFQGGGGFNSJKA-XHXSRVRCSA-N 0.000 description 1
• 231100000872 sexual dysfunction Toxicity 0.000 description 1
• 229960002855 simvastatin Drugs 0.000 description 1
• 229940001089 sinemet Drugs 0.000 description 1
• 208000020685 sleep-wake disease Diseases 0.000 description 1
• AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 239000012312 sodium hydride Substances 0.000 description 1
• 229910000104 sodium hydride Inorganic materials 0.000 description 1
• 235000010265 sodium sulphite Nutrition 0.000 description 1
• JGMJQSFLQWGYMQ-UHFFFAOYSA-M sodium;2,6-dichloro-n-phenylaniline;acetate Chemical compound [Na+].CC([O-])=O.ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1 JGMJQSFLQWGYMQ-UHFFFAOYSA-M 0.000 description 1
• 239000007901 soft capsule Substances 0.000 description 1
• 229950007874 solanezumab Drugs 0.000 description 1
• 208000018198 spasticity Diseases 0.000 description 1
• 238000004611 spectroscopical analysis Methods 0.000 description 1
• DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 1
• 229950001675 spiperone Drugs 0.000 description 1
• 210000000952 spleen Anatomy 0.000 description 1
• 238000010561 standard procedure Methods 0.000 description 1
• HKSZLNNOFSGOKW-FYTWVXJKSA-N staurosporine Chemical compound C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1[C@H]1C[C@@H](NC)[C@@H](OC)[C@]4(C)O1 HKSZLNNOFSGOKW-FYTWVXJKSA-N 0.000 description 1
• CGPUWJWCVCFERF-UHFFFAOYSA-N staurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(OC)O1 CGPUWJWCVCFERF-UHFFFAOYSA-N 0.000 description 1
• 239000012258 stirred mixture Substances 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 238000010254 subcutaneous injection Methods 0.000 description 1
• 239000007929 subcutaneous injection Substances 0.000 description 1
• WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 239000002511 suppository base Substances 0.000 description 1
• 230000009747 swallowing Effects 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 description 1
• 229960001367 tartaric acid Drugs 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 229940000238 tasmar Drugs 0.000 description 1
• 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
• 238000002560 therapeutic procedure Methods 0.000 description 1
• 125000002769 thiazolinyl group Chemical group 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• 125000003777 thiepinyl group Chemical group 0.000 description 1
• 125000002053 thietanyl group Chemical group 0.000 description 1
• 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 description 1
• 208000030045 thyroid gland papillary carcinoma Diseases 0.000 description 1
• 229960004523 tiletamine Drugs 0.000 description 1
• 231100000886 tinnitus Toxicity 0.000 description 1
• 210000001519 tissue Anatomy 0.000 description 1
• 238000003354 tissue distribution assay Methods 0.000 description 1
• 229940041597 tofranil Drugs 0.000 description 1
• 229960002309 toloxatone Drugs 0.000 description 1
• OOGJQPCLVADCPB-HXUWFJFHSA-N tolterodine Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C)C=2)O)=CC=CC=C1 OOGJQPCLVADCPB-HXUWFJFHSA-N 0.000 description 1
• 229960004045 tolterodine Drugs 0.000 description 1
• 239000006208 topical dosage form Substances 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• 239000012049 topical pharmaceutical composition Substances 0.000 description 1
• 231100000331 toxic Toxicity 0.000 description 1
• 230000002588 toxic effect Effects 0.000 description 1
• 229960003570 tramiprosate Drugs 0.000 description 1
• 229940035321 transderm scop Drugs 0.000 description 1
• 238000000844 transformation Methods 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 238000011830 transgenic mouse model Methods 0.000 description 1
• 229960003741 tranylcypromine Drugs 0.000 description 1
• 229950005135 traxoprodil Drugs 0.000 description 1
• 229960003991 trazodone Drugs 0.000 description 1
• 125000001425 triazolyl group Chemical group 0.000 description 1
• GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
• ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
• WUHSWAJJIXAIGL-UHFFFAOYSA-N trimethyl-[2-(pyrrolo[2,3-d]pyrimidin-7-ylmethoxy)ethyl]silane Chemical compound N1=CN=C2N(COCC[Si](C)(C)C)C=CC2=C1 WUHSWAJJIXAIGL-UHFFFAOYSA-N 0.000 description 1
• AWCQRXQAKUSEBJ-UHFFFAOYSA-N trimethyl-[2-[[5-(1-methylpyrazol-4-yl)-4-morpholin-4-ylpyrrolo[2,3-d]pyrimidin-7-yl]methoxy]ethyl]silane Chemical compound C1=NN(C)C=C1C1=CN(COCC[Si](C)(C)C)C2=NC=NC(N3CCOCC3)=C12 AWCQRXQAKUSEBJ-UHFFFAOYSA-N 0.000 description 1
• DJGMAJUNGLCGPI-UHFFFAOYSA-N trimethyl-[2-[[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-d]pyrimidin-7-yl]methoxy]ethyl]silane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CN(COCC[Si](C)(C)C)C2=NC=NC=C12 DJGMAJUNGLCGPI-UHFFFAOYSA-N 0.000 description 1
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
• 229960002431 trimipramine Drugs 0.000 description 1
• ZSCDBOWYZJWBIY-UHFFFAOYSA-N trimipramine Chemical compound C1CC2=CC=CC=C2N(CC(CN(C)C)C)C2=CC=CC=C21 ZSCDBOWYZJWBIY-UHFFFAOYSA-N 0.000 description 1
• 229910052722 tritium Inorganic materials 0.000 description 1
• 230000001228 trophic effect Effects 0.000 description 1
• ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
• 210000004291 uterus Anatomy 0.000 description 1
• BDIAUFOIMFAIPU-UHFFFAOYSA-N valepotriate Natural products CC(C)CC(=O)OC1C=C(C(=COC2OC(=O)CC(C)C)COC(C)=O)C2C11CO1 BDIAUFOIMFAIPU-UHFFFAOYSA-N 0.000 description 1
• 108010084171 vanutide cridificar Proteins 0.000 description 1
• 229960004688 venlafaxine Drugs 0.000 description 1
• 230000028973 vesicle-mediated transport Effects 0.000 description 1
• 210000001835 viscera Anatomy 0.000 description 1
• CKWXDLJHOHJWOX-UHFFFAOYSA-N voacangine hydroxyindolenine Natural products CCC1CC2N3CCC4(O)C(=Nc5ccc(OC)cc45)C2(CC1C3)C(=O)OC CKWXDLJHOHJWOX-UHFFFAOYSA-N 0.000 description 1
• 229940063674 voltaren Drugs 0.000 description 1
• 239000003643 water by type Substances 0.000 description 1
• 239000003871 white petrolatum Substances 0.000 description 1
• 238000010626 work up procedure Methods 0.000 description 1
• 229960002791 zimeldine Drugs 0.000 description 1
• 229940072168 zocor Drugs 0.000 description 1
• 229940020965 zoloft Drugs 0.000 description 1
• 229940083488 zonalon Drugs 0.000 description 1
• 229940061740 zyvox Drugs 0.000 description 1
• XZVHHLNLLVICFA-SNVBAGLBSA-N α-difluoromethyl-dopa Chemical compound FC(F)[C@](C(O)=O)(N)CC1=CC=C(O)C(O)=C1 XZVHHLNLLVICFA-SNVBAGLBSA-N 0.000 description 1