JP4981232B2 - ジアザビシクロ系中枢神経系活性薬剤 - Google Patents

Info

Publication number

JP4981232B2

JP4981232B2 JP2001578437A JP2001578437A JP4981232B2 JP 4981232 B2 JP4981232 B2 JP 4981232B2 JP 2001578437 A JP2001578437 A JP 2001578437A JP 2001578437 A JP2001578437 A JP 2001578437A JP 4981232 B2 JP4981232 B2 JP 4981232B2

Authority

JP

Japan

Prior art keywords

pyridinyl

diazabicyclo

cis

group

pyrrole

Prior art date

2000-04-27

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

• 210000003169 central nervous system Anatomy 0.000 title description 11
• 239000013543 active substance Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 415
• -1 nitro, 5-tetrazolyl Chemical group 0.000 claims description 164
• 229910052739 hydrogen Inorganic materials 0.000 claims description 120
• 239000001257 hydrogen Substances 0.000 claims description 118
• 125000000217 alkyl group Chemical group 0.000 claims description 108
• 229910052736 halogen Inorganic materials 0.000 claims description 62
• 150000002367 halogens Chemical class 0.000 claims description 62
• 150000002431 hydrogen Chemical class 0.000 claims description 61
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 57
• 125000003545 alkoxy group Chemical group 0.000 claims description 43
• 150000003839 salts Chemical class 0.000 claims description 41
• 238000011282 treatment Methods 0.000 claims description 39
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 33
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 31
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 27
• 125000000304 alkynyl group Chemical group 0.000 claims description 26
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
• 230000036407 pain Effects 0.000 claims description 26
• 208000002193 Pain Diseases 0.000 claims description 25
• 125000003342 alkenyl group Chemical group 0.000 claims description 25
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 25
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 24
• 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 24
• 125000001188 haloalkyl group Chemical group 0.000 claims description 23
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
• 208000035475 disorder Diseases 0.000 claims description 21
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims description 19
• 241000124008 Mammalia Species 0.000 claims description 18
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 17
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 16
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 15
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 15
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 15
• 125000004414 alkyl thio group Chemical group 0.000 claims description 15
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 15
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 15
• 125000004967 formylalkyl group Chemical group 0.000 claims description 15
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 14
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 13
• 125000005358 mercaptoalkyl group Chemical group 0.000 claims description 13
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 12
• SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 11
• 229960002715 nicotine Drugs 0.000 claims description 11
• 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 11
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 11
• 239000003937 drug carrier Substances 0.000 claims description 10
• SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 10
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 8
• 208000024827 Alzheimer disease Diseases 0.000 claims description 7
• 208000018737 Parkinson disease Diseases 0.000 claims description 7
• 230000003957 neurotransmitter release Effects 0.000 claims description 6
• OGULMRQWNAMFPB-GMSGAONNSA-N (1r,5s)-6-(5-bromopyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound BrC1=CN=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 OGULMRQWNAMFPB-GMSGAONNSA-N 0.000 claims description 5
• BWQKEWGYFNUHHX-VXNVDRBHSA-N (1r,5s)-6-(6-bromo-5-methoxypyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1=C(Br)C(OC)=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 BWQKEWGYFNUHHX-VXNVDRBHSA-N 0.000 claims description 5
• RZYCOPGGQSSESS-VXNVDRBHSA-N (1r,5s)-6-(6-chloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound C1=NC(Cl)=CC=C1N1[C@@H]2CNC[C@@H]2C1 RZYCOPGGQSSESS-VXNVDRBHSA-N 0.000 claims description 5
• XHYQJTGLPJMMEB-PSASIEDQSA-N (1r,5s)-6-pyridin-3-yl-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1([C@@H]2CNC[C@@H]2C1)C1=CC=CN=C1 XHYQJTGLPJMMEB-PSASIEDQSA-N 0.000 claims description 5
• IQCDZVRYLPBQRD-CABZTGNLSA-N (1s,6r)-7-(5-methoxypyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound COC1=CN=CC(N2[C@H]3CNCC[C@H]3C2)=C1 IQCDZVRYLPBQRD-CABZTGNLSA-N 0.000 claims description 5
• OSOHWFWLNDUPPP-WPRPVWTQSA-N (1s,6r)-7-(6-chloropyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound C1=NC(Cl)=CC=C1N1[C@H]2CNCC[C@H]2C1 OSOHWFWLNDUPPP-WPRPVWTQSA-N 0.000 claims description 5
• QZPCTRNKBFDOCH-AOOOYVTPSA-N (3as,6ar)-5-(6-chloropyridin-3-yl)-2-methyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole Chemical compound C([C@@H]1CN(C[C@@H]1C1)C)N1C1=CC=C(Cl)N=C1 QZPCTRNKBFDOCH-AOOOYVTPSA-N 0.000 claims description 5
• 229940123445 Tricyclic antidepressant Drugs 0.000 claims description 5
• KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 5
• 239000003029 tricyclic antidepressant agent Substances 0.000 claims description 5
• IWMPNPIMHCIYMC-HZGVNTEJSA-N (1r,5s)-6-(5,6-dichloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1=C(Cl)C(Cl)=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 IWMPNPIMHCIYMC-HZGVNTEJSA-N 0.000 claims description 4
• GCTVZTULKNGORX-PSASIEDQSA-N (1r,5s)-6-(6-chloro-5-methylpyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1=C(Cl)C(C)=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 GCTVZTULKNGORX-PSASIEDQSA-N 0.000 claims description 4
• YHOMDZMYCWJHFA-WPRPVWTQSA-N (1s,6r)-4-(6-chloropyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound C1=NC(Cl)=CC=C1N1C[C@@H]2NC[C@@H]2CC1 YHOMDZMYCWJHFA-WPRPVWTQSA-N 0.000 claims description 4
• UXNFBEZSLURUHM-ONGXEEELSA-N (1s,6r)-7-(6-chloro-5-methylpyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound N1=C(Cl)C(C)=CC(N2[C@H]3CNCC[C@H]3C2)=C1 UXNFBEZSLURUHM-ONGXEEELSA-N 0.000 claims description 4
• NHOKDBHEVHBXTJ-ONGXEEELSA-N (1s,6r)-7-pyridin-3-yl-4,7-diazabicyclo[4.2.0]octane Chemical compound N1([C@H]2CNCC[C@H]2C1)C1=CC=CN=C1 NHOKDBHEVHBXTJ-ONGXEEELSA-N 0.000 claims description 4
• FZHVWHFLHSHANF-SCZZXKLOSA-N (3ar,6ar)-1-(6-chloropyridin-3-yl)-3,3a,4,5,6,6a-hexahydro-2h-pyrrolo[2,3-c]pyrrole Chemical compound C1=NC(Cl)=CC=C1N1[C@H]2CNC[C@H]2CC1 FZHVWHFLHSHANF-SCZZXKLOSA-N 0.000 claims description 4
• DQHQCRQWOJTKBG-SCZZXKLOSA-N (3ar,6ar)-5-(6-chloropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound C1=NC(Cl)=CC=C1N1C[C@@H]2NCC[C@@H]2C1 DQHQCRQWOJTKBG-SCZZXKLOSA-N 0.000 claims description 4
• VUGNXGAJCUBYBO-DTORHVGOSA-N 5-[(3as,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrol-5-yl]pyridin-3-ol Chemical compound OC1=CN=CC(N2C[C@H]3CNC[C@H]3C2)=C1 VUGNXGAJCUBYBO-DTORHVGOSA-N 0.000 claims description 4
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 4
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 4
• 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
• 208000000323 Tourette Syndrome Diseases 0.000 claims description 4
• 208000016620 Tourette disease Diseases 0.000 claims description 4
• 239000001961 anticonvulsive agent Substances 0.000 claims description 4
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 4
• 201000000980 schizophrenia Diseases 0.000 claims description 4
• RZYCOPGGQSSESS-CBAPKCEASA-N (1s,5r)-6-(6-chloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound C1=NC(Cl)=CC=C1N1[C@H]2CNC[C@H]2C1 RZYCOPGGQSSESS-CBAPKCEASA-N 0.000 claims description 3
• XHYQJTGLPJMMEB-WPRPVWTQSA-N (1s,5r)-6-pyridin-3-yl-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1([C@H]2CNC[C@H]2C1)C1=CC=CN=C1 XHYQJTGLPJMMEB-WPRPVWTQSA-N 0.000 claims description 3
• ZUQWAAYYWZDXPL-IONNQARKSA-N (1s,5s)-3-(6-chloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound C1=NC(Cl)=CC=C1N1C[C@H]2NC[C@H]2C1 ZUQWAAYYWZDXPL-IONNQARKSA-N 0.000 claims description 3
• VXCWOKWPZDBULP-XVKPBYJWSA-N (1s,6r)-7-(5,6-dichloropyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound N1=C(Cl)C(Cl)=CC(N2[C@H]3CNCC[C@H]3C2)=C1 VXCWOKWPZDBULP-XVKPBYJWSA-N 0.000 claims description 3
• NBPGBNNVEWLKEW-KOLCDFICSA-N (3ar,6ar)-1-pyridin-3-yl-3,3a,4,5,6,6a-hexahydro-2h-pyrrolo[2,3-c]pyrrole Chemical compound C([C@@H]1CNC[C@@H]11)CN1C1=CC=CN=C1 NBPGBNNVEWLKEW-KOLCDFICSA-N 0.000 claims description 3
• ZJLSTXGOFNDPFN-YPMHNXCESA-N (3ar,6ar)-5-(5-ethenylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound C=CC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 ZJLSTXGOFNDPFN-YPMHNXCESA-N 0.000 claims description 3
• OUNUIZLSDCKVGG-PWSUYJOCSA-N (3ar,6ar)-5-(5-methylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound CC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 OUNUIZLSDCKVGG-PWSUYJOCSA-N 0.000 claims description 3
• SLNSBOHQJODUJZ-SCZZXKLOSA-N (3ar,6ar)-5-(6-bromo-5-methoxypyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound N1=C(Br)C(OC)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 SLNSBOHQJODUJZ-SCZZXKLOSA-N 0.000 claims description 3
• KEKVMZXOMNEOQP-KOLCDFICSA-N (3ar,6ar)-5-(6-bromo-5-methylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound N1=C(Br)C(C)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 KEKVMZXOMNEOQP-KOLCDFICSA-N 0.000 claims description 3
• QCAHYIYDXVYFOH-AOOOYVTPSA-N (3as,6ar)-5-(5-methoxypyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound COC1=CN=CC(N2C[C@H]3CNC[C@H]3C2)=C1 QCAHYIYDXVYFOH-AOOOYVTPSA-N 0.000 claims description 3
• SCDHSPWBVXFHFI-PWSUYJOCSA-N 5-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]pyridine-3-carbonitrile Chemical compound N#CC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 SCDHSPWBVXFHFI-PWSUYJOCSA-N 0.000 claims description 3
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
• 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 3
• ZUQWAAYYWZDXPL-APPZFPTMSA-N (1r,5r)-3-(6-chloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound C1=NC(Cl)=CC=C1N1C[C@@H]2NC[C@@H]2C1 ZUQWAAYYWZDXPL-APPZFPTMSA-N 0.000 claims description 2
• BSDFRUMXKRLPJN-NXEZZACHSA-N (1r,5r)-4-pyridin-3-yl-4,7-diazabicyclo[3.2.0]heptane Chemical compound C([C@H]1NC[C@@H]21)CN2C1=CC=CN=C1 BSDFRUMXKRLPJN-NXEZZACHSA-N 0.000 claims description 2
• LVRYCPLQUQOATD-RKDXNWHRSA-N (1r,5r)-7-(6-chloropyridin-3-yl)-4,7-diazabicyclo[3.2.0]heptane Chemical compound C1=NC(Cl)=CC=C1N1[C@@H]2CCN[C@@H]2C1 LVRYCPLQUQOATD-RKDXNWHRSA-N 0.000 claims description 2
• CIYRARKCUJBDET-ZYHUDNBSSA-N (1r,5s)-6-(5-ethynylpyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound C#CC1=CN=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 CIYRARKCUJBDET-ZYHUDNBSSA-N 0.000 claims description 2
• IBEGQZNIXSCPIN-LDYMZIIASA-N (1r,5s)-6-(5-methoxypyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound COC1=CN=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 IBEGQZNIXSCPIN-LDYMZIIASA-N 0.000 claims description 2
• VXCWOKWPZDBULP-GMSGAONNSA-N (1r,6s)-7-(5,6-dichloropyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound N1=C(Cl)C(Cl)=CC(N2[C@@H]3CNCC[C@@H]3C2)=C1 VXCWOKWPZDBULP-GMSGAONNSA-N 0.000 claims description 2
• UXNFBEZSLURUHM-MWLCHTKSSA-N (1r,6s)-7-(6-chloro-5-methylpyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound N1=C(Cl)C(C)=CC(N2[C@@H]3CNCC[C@@H]3C2)=C1 UXNFBEZSLURUHM-MWLCHTKSSA-N 0.000 claims description 2
• NHOKDBHEVHBXTJ-MWLCHTKSSA-N (1r,6s)-7-pyridin-3-yl-4,7-diazabicyclo[4.2.0]octane Chemical compound N1([C@@H]2CNCC[C@@H]2C1)C1=CC=CN=C1 NHOKDBHEVHBXTJ-MWLCHTKSSA-N 0.000 claims description 2
• IWMPNPIMHCIYMC-RCOVLWMOSA-N (1s,5r)-6-(5,6-dichloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1=C(Cl)C(Cl)=CC(N2[C@H]3CNC[C@H]3C2)=C1 IWMPNPIMHCIYMC-RCOVLWMOSA-N 0.000 claims description 2
• GIAHXLMUQPRJBC-JQWIXIFHSA-N (1s,5r)-6-(5-ethenylpyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound C=CC1=CN=CC(N2[C@H]3CNC[C@H]3C2)=C1 GIAHXLMUQPRJBC-JQWIXIFHSA-N 0.000 claims description 2
• CIYRARKCUJBDET-JQWIXIFHSA-N (1s,5r)-6-(5-ethynylpyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound C#CC1=CN=CC(N2[C@H]3CNC[C@H]3C2)=C1 CIYRARKCUJBDET-JQWIXIFHSA-N 0.000 claims description 2
• IBEGQZNIXSCPIN-KWQFWETISA-N (1s,5r)-6-(5-methoxypyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound COC1=CN=CC(N2[C@H]3CNC[C@H]3C2)=C1 IBEGQZNIXSCPIN-KWQFWETISA-N 0.000 claims description 2
• WBDWMCKZWXJEHV-ONGXEEELSA-N (1s,5r)-6-(6-bromo-5-ethenylpyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound C1=C(C=C)C(Br)=NC=C1N1[C@H]2CNC[C@H]2C1 WBDWMCKZWXJEHV-ONGXEEELSA-N 0.000 claims description 2
• GCTVZTULKNGORX-WPRPVWTQSA-N (1s,5r)-6-(6-chloro-5-methylpyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1=C(Cl)C(C)=CC(N2[C@H]3CNC[C@H]3C2)=C1 GCTVZTULKNGORX-WPRPVWTQSA-N 0.000 claims description 2
• MBQYQLWSBRANKQ-IMTBSYHQSA-N (1s,5s)-3-(5,6-dichloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1=C(Cl)C(Cl)=CC(N2C[C@H]3NC[C@H]3C2)=C1 MBQYQLWSBRANKQ-IMTBSYHQSA-N 0.000 claims description 2
• UYZGGVMCTYTMRJ-WCBMZHEXSA-N (1s,5s)-3-pyridin-3-yl-3,6-diazabicyclo[3.2.0]heptane Chemical compound C([C@H]1NC[C@H]1C1)N1C1=CC=CN=C1 UYZGGVMCTYTMRJ-WCBMZHEXSA-N 0.000 claims description 2
• FDOUKQXLQIXJFX-ONGXEEELSA-N (1s,6r)-4-pyridin-3-yl-4,7-diazabicyclo[4.2.0]octane Chemical compound C([C@@H]1NC[C@@H]1CC1)N1C1=CC=CN=C1 FDOUKQXLQIXJFX-ONGXEEELSA-N 0.000 claims description 2
• QULYNSGTKPCWSF-XCBNKYQSSA-N (3ar,6ar)-5-(5,6-dichloropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound N1=C(Cl)C(Cl)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 QULYNSGTKPCWSF-XCBNKYQSSA-N 0.000 claims description 2
• SUMBPLBCXUNGMO-KCJUWKMLSA-N (3ar,6ar)-5-(5-bromopyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound BrC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 SUMBPLBCXUNGMO-KCJUWKMLSA-N 0.000 claims description 2
• KWZWPEDWONELEI-YPMHNXCESA-N (3ar,6ar)-5-(5-ethylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound CCC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 KWZWPEDWONELEI-YPMHNXCESA-N 0.000 claims description 2
• FDUANQGPNHRGGA-YPMHNXCESA-N (3ar,6ar)-5-(5-ethynylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound C#CC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 FDUANQGPNHRGGA-YPMHNXCESA-N 0.000 claims description 2
• YSAVCILVSULFGD-SKDRFNHKSA-N (3ar,6ar)-5-(5-methoxypyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound COC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 YSAVCILVSULFGD-SKDRFNHKSA-N 0.000 claims description 2
• ZCIPXINQRZWYCD-XCBNKYQSSA-N (3ar,6ar)-5-(6-bromo-5-chloropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound N1=C(Br)C(Cl)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 ZCIPXINQRZWYCD-XCBNKYQSSA-N 0.000 claims description 2
• JCSPUVOHNHERBJ-PWSUYJOCSA-N (3ar,6ar)-5-(6-bromo-5-ethenylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound C1=C(C=C)C(Br)=NC=C1N1C[C@@H]2NCC[C@@H]2C1 JCSPUVOHNHERBJ-PWSUYJOCSA-N 0.000 claims description 2
• RUEPBFNTOSWZAB-KOLCDFICSA-N (3ar,6ar)-5-(6-chloro-5-methylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound N1=C(Cl)C(C)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 RUEPBFNTOSWZAB-KOLCDFICSA-N 0.000 claims description 2
• HMWDILXJWAOEJT-KOLCDFICSA-N (3ar,6ar)-5-pyridin-3-yl-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound C([C@H]1CCN[C@H]1C1)N1C1=CC=CN=C1 HMWDILXJWAOEJT-KOLCDFICSA-N 0.000 claims description 2
• OHWQUEIYHPZQPN-TXEJJXNPSA-N (3ar,6as)-5-(5-propoxypyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound CCCOC1=CN=CC(N2C[C@H]3CNC[C@H]3C2)=C1 OHWQUEIYHPZQPN-TXEJJXNPSA-N 0.000 claims description 2
• GGWINWDBVWLKNK-AOOOYVTPSA-N (3ar,6as)-5-(6-chloro-5-methylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound N1=C(Cl)C(C)=CC(N2C[C@H]3CNC[C@H]3C2)=C1 GGWINWDBVWLKNK-AOOOYVTPSA-N 0.000 claims description 2
• VPFXUOCTXHVJCT-DTORHVGOSA-N (3as,6ar)-5-(6-chloro-5-methoxypyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound N1=C(Cl)C(OC)=CC(N2C[C@H]3CNC[C@H]3C2)=C1 VPFXUOCTXHVJCT-DTORHVGOSA-N 0.000 claims description 2
• FZHVWHFLHSHANF-WCBMZHEXSA-N (3as,6as)-1-(6-chloropyridin-3-yl)-3,3a,4,5,6,6a-hexahydro-2h-pyrrolo[2,3-c]pyrrole Chemical compound C1=NC(Cl)=CC=C1N1[C@@H]2CNC[C@@H]2CC1 FZHVWHFLHSHANF-WCBMZHEXSA-N 0.000 claims description 2
• NBPGBNNVEWLKEW-GXSJLCMTSA-N (3as,6as)-1-pyridin-3-yl-3,3a,4,5,6,6a-hexahydro-2h-pyrrolo[2,3-c]pyrrole Chemical compound C([C@H]1CNC[C@H]11)CN1C1=CC=CN=C1 NBPGBNNVEWLKEW-GXSJLCMTSA-N 0.000 claims description 2
• QULYNSGTKPCWSF-OIBJUYFYSA-N (3as,6as)-5-(5,6-dichloropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound N1=C(Cl)C(Cl)=CC(N2C[C@H]3NCC[C@H]3C2)=C1 QULYNSGTKPCWSF-OIBJUYFYSA-N 0.000 claims description 2
• SUMBPLBCXUNGMO-GZMMTYOYSA-N (3as,6as)-5-(5-bromopyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound BrC1=CN=CC(N2C[C@H]3NCC[C@H]3C2)=C1 SUMBPLBCXUNGMO-GZMMTYOYSA-N 0.000 claims description 2
• YSAVCILVSULFGD-JOYOIKCWSA-N (3as,6as)-5-(5-methoxypyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound COC1=CN=CC(N2C[C@H]3NCC[C@H]3C2)=C1 YSAVCILVSULFGD-JOYOIKCWSA-N 0.000 claims description 2
• RUEPBFNTOSWZAB-GXSJLCMTSA-N (3as,6as)-5-(6-chloro-5-methylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound N1=C(Cl)C(C)=CC(N2C[C@H]3NCC[C@H]3C2)=C1 RUEPBFNTOSWZAB-GXSJLCMTSA-N 0.000 claims description 2
• DQHQCRQWOJTKBG-WCBMZHEXSA-N (3as,6as)-5-(6-chloropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound C1=NC(Cl)=CC=C1N1C[C@H]2NCC[C@H]2C1 DQHQCRQWOJTKBG-WCBMZHEXSA-N 0.000 claims description 2
• HMWDILXJWAOEJT-GXSJLCMTSA-N (3as,6as)-5-pyridin-3-yl-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound C([C@@H]1CCN[C@@H]1C1)N1C1=CC=CN=C1 HMWDILXJWAOEJT-GXSJLCMTSA-N 0.000 claims description 2
• YEUYAIVZZOYQGC-KOLCDFICSA-N (4ar,7ar)-6-(6-chloropyridin-3-yl)-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridine Chemical compound C1=NC(Cl)=CC=C1N1C[C@@H]2NCCC[C@@H]2C1 YEUYAIVZZOYQGC-KOLCDFICSA-N 0.000 claims description 2
• WBIYGACFBGCOKV-PWSUYJOCSA-N 2-[5-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-2-bromopyridin-3-yl]acetonitrile Chemical compound C1=C(CC#N)C(Br)=NC=C1N1C[C@@H]2NCC[C@@H]2C1 WBIYGACFBGCOKV-PWSUYJOCSA-N 0.000 claims description 2
• KQMSAFWRVJCRPS-PSASIEDQSA-N 2-bromo-5-[(1r,5s)-3,6-diazabicyclo[3.2.0]heptan-6-yl]pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(Br)=NC=C1N1[C@@H]2CNC[C@@H]2C1 KQMSAFWRVJCRPS-PSASIEDQSA-N 0.000 claims description 2
• KLNHDAVAIWEDTG-BETUJISGSA-N 3-[(3ar,6as)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrol-5-yl]quinoline Chemical compound C1=CC=CC2=CC(N3C[C@H]4CNC[C@H]4C3)=CN=C21 KLNHDAVAIWEDTG-BETUJISGSA-N 0.000 claims description 2
• KGHKOOLJKCBUSS-KOLCDFICSA-N 5-[(1r,5r)-3,6-diazabicyclo[3.2.0]heptan-3-yl]pyridine-3-carbonitrile Chemical compound N#CC1=CN=CC(N2C[C@@H]3NC[C@@H]3C2)=C1 KGHKOOLJKCBUSS-KOLCDFICSA-N 0.000 claims description 2
• GPXAWLDGWSBLKM-MWLCHTKSSA-N 5-[(1r,5s)-3,6-diazabicyclo[3.2.0]heptan-6-yl]pyridine-3-carbonitrile Chemical compound N#CC1=CN=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 GPXAWLDGWSBLKM-MWLCHTKSSA-N 0.000 claims description 2
• YKOUMOZMCMIKMG-ZYHUDNBSSA-N 5-[(1r,6s)-4,7-diazabicyclo[4.2.0]octan-7-yl]pyridine-3-carbonitrile Chemical compound N#CC1=CN=CC(N2[C@@H]3CNCC[C@@H]3C2)=C1 YKOUMOZMCMIKMG-ZYHUDNBSSA-N 0.000 claims description 2
• YKOUMOZMCMIKMG-JQWIXIFHSA-N 5-[(1s,6r)-4,7-diazabicyclo[4.2.0]octan-7-yl]pyridine-3-carbonitrile Chemical compound N#CC1=CN=CC(N2[C@H]3CNCC[C@H]3C2)=C1 YKOUMOZMCMIKMG-JQWIXIFHSA-N 0.000 claims description 2
• MMCDYLWYKBYYMX-KCJUWKMLSA-N 5-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-2-bromopyridine-3-carbonitrile Chemical compound C1=C(C#N)C(Br)=NC=C1N1C[C@@H]2NCC[C@@H]2C1 MMCDYLWYKBYYMX-KCJUWKMLSA-N 0.000 claims description 2
• JJRVGUPFYLTYGR-PWSUYJOCSA-N 5-[(3ar,6ar)-3,3a,4,5,6,6a-hexahydro-2h-pyrrolo[2,3-c]pyrrol-1-yl]pyridine-3-carbonitrile Chemical compound N#CC1=CN=CC(N2[C@H]3CNC[C@H]3CC2)=C1 JJRVGUPFYLTYGR-PWSUYJOCSA-N 0.000 claims description 2
• IZNGUHXSMKBUJT-GZMMTYOYSA-N 5-[(3as,6as)-3,3a,4,5,6,6a-hexahydro-2h-pyrrolo[2,3-c]pyrrol-1-yl]pyridin-3-ol Chemical compound OC1=CN=CC(N2[C@@H]3CNC[C@@H]3CC2)=C1 IZNGUHXSMKBUJT-GZMMTYOYSA-N 0.000 claims description 2
• WZWFSJDVABFXKU-CMPLNLGQSA-N C([C@@H]1CCN[C@@H]1C1)CN1C1=CC=CN=C1 Chemical compound C([C@@H]1CCN[C@@H]1C1)CN1C1=CC=CN=C1 WZWFSJDVABFXKU-CMPLNLGQSA-N 0.000 claims description 2
• GZQLLEREELILKV-KOLCDFICSA-N C([C@@H]1CN(C[C@@H]11)C)CN1C1=CC=C(Cl)N=C1 Chemical compound C([C@@H]1CN(C[C@@H]11)C)CN1C1=CC=C(Cl)N=C1 GZQLLEREELILKV-KOLCDFICSA-N 0.000 claims description 2
• WADIUSKZZWETGD-KCJUWKMLSA-N [5-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-2-bromopyridin-3-yl]methanol Chemical compound N1=C(Br)C(CO)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 WADIUSKZZWETGD-KCJUWKMLSA-N 0.000 claims description 2
• GPXAWLDGWSBLKM-ONGXEEELSA-N a-366,833 Chemical compound N#CC1=CN=CC(N2[C@H]3CNC[C@H]3C2)=C1 GPXAWLDGWSBLKM-ONGXEEELSA-N 0.000 claims description 2
• 230000001773 anti-convulsant effect Effects 0.000 claims description 2
• 229960003965 antiepileptics Drugs 0.000 claims description 2
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 3
• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims 2
• IQCDZVRYLPBQRD-BXKDBHETSA-N (1r,6s)-7-(5-methoxypyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound COC1=CN=CC(N2[C@@H]3CNCC[C@@H]3C2)=C1 IQCDZVRYLPBQRD-BXKDBHETSA-N 0.000 claims 1
• YETODIXQMRZKEG-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropyrrolo[2,3-c]pyrrole Chemical compound C1NCC2NCCC21 YETODIXQMRZKEG-UHFFFAOYSA-N 0.000 claims 1
• ISZLKMRXFZKNAQ-UHFFFAOYSA-N 1,2-diazabicyclo[3.2.0]heptane Chemical compound N1CCC2CCN21 ISZLKMRXFZKNAQ-UHFFFAOYSA-N 0.000 claims 1
• 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 1
• 206010048010 Withdrawal syndrome Diseases 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 228
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 219
• 239000000047 product Substances 0.000 description 199
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 197
• CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 188
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 184
• 229910000069 nitrogen hydride Inorganic materials 0.000 description 181
• 239000000243 solution Substances 0.000 description 174
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 159
• 238000000034 method Methods 0.000 description 158
• 239000000203 mixture Substances 0.000 description 158
• 230000002829 reductive effect Effects 0.000 description 112
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 102
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 91
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 91
• 235000019439 ethyl acetate Nutrition 0.000 description 76
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 75
• 239000007787 solid Substances 0.000 description 71
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
• 238000000921 elemental analysis Methods 0.000 description 58
• 238000004364 calculation method Methods 0.000 description 57
• 238000005160 1H NMR spectroscopy Methods 0.000 description 55
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 55
• 238000005481 NMR spectroscopy Methods 0.000 description 54
• 235000019441 ethanol Nutrition 0.000 description 53
• 239000003921 oil Substances 0.000 description 52
• 235000019198 oils Nutrition 0.000 description 52
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 50
• 239000000377 silicon dioxide Substances 0.000 description 49
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
• 229910052681 coesite Inorganic materials 0.000 description 48
• 229910052906 cristobalite Inorganic materials 0.000 description 48
• 229910052682 stishovite Inorganic materials 0.000 description 48
• 229910052905 tridymite Inorganic materials 0.000 description 48
• 239000000706 filtrate Substances 0.000 description 42
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 37
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 34
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 34
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 31
• 239000003814 drug Substances 0.000 description 29
• 239000012267 brine Substances 0.000 description 26
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 26
• 238000003756 stirring Methods 0.000 description 26
• 229940079593 drug Drugs 0.000 description 25
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 23
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 22
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 21
• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 21
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 20
• 239000011541 reaction mixture Substances 0.000 description 20
• 230000000694 effects Effects 0.000 description 19
• 239000012458 free base Substances 0.000 description 19
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 19
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 18
• 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 description 18
• 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 description 18
• 239000002858 neurotransmitter agent Substances 0.000 description 18
• 238000000746 purification Methods 0.000 description 18
• 239000000126 substance Substances 0.000 description 18
• 239000012043 crude product Substances 0.000 description 17
• 239000012074 organic phase Substances 0.000 description 17
• 229910052763 palladium Inorganic materials 0.000 description 17
• 239000003054 catalyst Substances 0.000 description 16
• 238000001311 chemical methods and process Methods 0.000 description 16
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
• 238000001914 filtration Methods 0.000 description 15
• 239000000651 prodrug Substances 0.000 description 15
• 229940002612 prodrug Drugs 0.000 description 15
• 239000001530 fumaric acid Substances 0.000 description 14
• 239000007864 aqueous solution Substances 0.000 description 13
• MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group 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 13
• 238000010992 reflux Methods 0.000 description 13
• NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 12
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 12
• 239000012230 colorless oil Substances 0.000 description 12
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 12
• 238000010438 heat treatment Methods 0.000 description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
• 125000003118 aryl group Chemical group 0.000 description 11
• 230000001242 postsynaptic effect Effects 0.000 description 11
• 230000005062 synaptic transmission Effects 0.000 description 11
• 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 10
• CWUSSMOAVKKWJU-OCAPTIKFSA-N (3ar,6as)-5-(5,6-dichloropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound N1=C(Cl)C(Cl)=CC(N2C[C@H]3CNC[C@H]3C2)=C1 CWUSSMOAVKKWJU-OCAPTIKFSA-N 0.000 description 10
• PEAOEIWYQVXZMB-UHFFFAOYSA-N 5-bromo-2-chloropyridine Chemical compound ClC1=CC=C(Br)C=N1 PEAOEIWYQVXZMB-UHFFFAOYSA-N 0.000 description 10
• 239000002253 acid Substances 0.000 description 10
• 210000004027 cell Anatomy 0.000 description 10
• 239000013078 crystal Substances 0.000 description 10
• 239000000284 extract Substances 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• 102000005962 receptors Human genes 0.000 description 10
• 108020003175 receptors Proteins 0.000 description 10
• 230000001225 therapeutic effect Effects 0.000 description 10
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 9
• 239000005909 Kieselgur Substances 0.000 description 9
• 241001465754 Metazoa Species 0.000 description 9
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• 239000012298 atmosphere Substances 0.000 description 9
• 238000006243 chemical reaction Methods 0.000 description 9
• 150000002148 esters Chemical class 0.000 description 9
• 239000007924 injection Substances 0.000 description 9
• 238000002347 injection Methods 0.000 description 9
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
• 238000012360 testing method Methods 0.000 description 9
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 9
• 150000001412 amines Chemical class 0.000 description 8
• 125000004432 carbon atom Chemical group C* 0.000 description 8
• JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 8
• 239000003446 ligand Substances 0.000 description 8
• 239000012528 membrane Substances 0.000 description 8
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
• 239000012044 organic layer Substances 0.000 description 8
• 239000002904 solvent Substances 0.000 description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
• SOSPMXMEOFGPIM-UHFFFAOYSA-N 3,5-dibromopyridine Chemical compound BrC1=CN=CC(Br)=C1 SOSPMXMEOFGPIM-UHFFFAOYSA-N 0.000 description 7
• 239000007832 Na2SO4 Substances 0.000 description 7
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 7
• IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 7
• 239000002585 base Substances 0.000 description 7
• 239000003795 chemical substances by application Substances 0.000 description 7
• HEDRZPFGACZZDS-MICDWDOJSA-N deuterated chloroform Substances [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
• 125000000623 heterocyclic group Chemical group 0.000 description 7
• 230000002401 inhibitory effect Effects 0.000 description 7
• 229940011051 isopropyl acetate Drugs 0.000 description 7
• 239000002502 liposome Substances 0.000 description 7
• 239000012280 lithium aluminium hydride Substances 0.000 description 7
• 229910052757 nitrogen Inorganic materials 0.000 description 7
• 239000002244 precipitate Substances 0.000 description 7
• 239000011734 sodium Substances 0.000 description 7
• 229910000029 sodium carbonate Inorganic materials 0.000 description 7
• 229910052938 sodium sulfate Inorganic materials 0.000 description 7
• 108091006146 Channels Proteins 0.000 description 6
• UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 6
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
• 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 6
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• 238000002441 X-ray diffraction Methods 0.000 description 6
• 238000010521 absorption reaction Methods 0.000 description 6
• 229940035676 analgesics Drugs 0.000 description 6
• 239000000730 antalgic agent Substances 0.000 description 6
• 230000015572 biosynthetic process Effects 0.000 description 6
• 239000000872 buffer Substances 0.000 description 6
• 239000003153 chemical reaction reagent Substances 0.000 description 6
• 229960003638 dopamine Drugs 0.000 description 6
• 239000012065 filter cake Substances 0.000 description 6
• 150000002430 hydrocarbons Chemical class 0.000 description 6
• 238000001727 in vivo Methods 0.000 description 6
• 238000002844 melting Methods 0.000 description 6
• 230000008018 melting Effects 0.000 description 6
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 6
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 6
• 229940005483 opioid analgesics Drugs 0.000 description 6
• 239000000546 pharmaceutical excipient Substances 0.000 description 6
• 239000000843 powder Substances 0.000 description 6
• 229920006395 saturated elastomer Polymers 0.000 description 6
• 238000000926 separation method Methods 0.000 description 6
• 229910052708 sodium Inorganic materials 0.000 description 6
• 238000003786 synthesis reaction Methods 0.000 description 6
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
• 239000006260 foam Substances 0.000 description 5
• GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 5
• 235000019341 magnesium sulphate Nutrition 0.000 description 5
• KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 5
• 229910000027 potassium carbonate Inorganic materials 0.000 description 5
• 230000003518 presynaptic effect Effects 0.000 description 5
• 239000000741 silica gel Substances 0.000 description 5
• 229910002027 silica gel Inorganic materials 0.000 description 5
• 239000000725 suspension Substances 0.000 description 5
• 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 5
• ZPAUUYOZUOKYRA-FLMPKHPASA-N (e)-but-2-enedioic acid;(1r,5s)-6-(6-chloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound OC(=O)\C=C\C(O)=O.C1=NC(Cl)=CC=C1N1[C@@H]2CNC[C@@H]2C1 ZPAUUYOZUOKYRA-FLMPKHPASA-N 0.000 description 4
• NTYRHVKKVDBMKC-DDSSZZOXSA-N (e)-but-2-enedioic acid;(1r,5s)-6-pyridin-3-yl-3,6-diazabicyclo[3.2.0]heptane Chemical compound OC(=O)\C=C\C(O)=O.N1([C@@H]2CNC[C@@H]2C1)C1=CC=CN=C1 NTYRHVKKVDBMKC-DDSSZZOXSA-N 0.000 description 4
• QWLGCWXSNYKKDO-UHFFFAOYSA-N 2-chloro-5-iodopyridine Chemical compound ClC1=CC=C(I)C=N1 QWLGCWXSNYKKDO-UHFFFAOYSA-N 0.000 description 4
• 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 4
• YTSKHJMMNFPBBZ-UHFFFAOYSA-N 5-bromo-2-chloro-3-methylpyridine Chemical compound CC1=CC(Br)=CN=C1Cl YTSKHJMMNFPBBZ-UHFFFAOYSA-N 0.000 description 4
• 206010001497 Agitation Diseases 0.000 description 4
• 206010012289 Dementia Diseases 0.000 description 4
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
• 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 4
• 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 4
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
• OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 4
• 229960004373 acetylcholine Drugs 0.000 description 4
• 230000009471 action Effects 0.000 description 4
• 150000001299 aldehydes Chemical class 0.000 description 4
• 150000001414 amino alcohols Chemical class 0.000 description 4
• 125000003277 amino group Chemical group 0.000 description 4
• 230000000202 analgesic effect Effects 0.000 description 4
• 239000008346 aqueous phase Substances 0.000 description 4
• XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 4
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 4
• 210000004556 brain Anatomy 0.000 description 4
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
• 230000001713 cholinergic effect Effects 0.000 description 4
• 201000010099 disease Diseases 0.000 description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
• 235000019253 formic acid Nutrition 0.000 description 4
• 238000009472 formulation Methods 0.000 description 4
• 239000010410 layer Substances 0.000 description 4
• 239000007788 liquid Substances 0.000 description 4
• 230000014759 maintenance of location Effects 0.000 description 4
• 230000001537 neural effect Effects 0.000 description 4
• 231100000252 nontoxic Toxicity 0.000 description 4
• 230000003000 nontoxic effect Effects 0.000 description 4
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 4
• IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 4
• 229920001223 polyethylene glycol Polymers 0.000 description 4
• 125000001424 substituent group Chemical group 0.000 description 4
• 229910052717 sulfur Inorganic materials 0.000 description 4
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
• 125000003396 thiol group Chemical class [H]S* 0.000 description 4
• JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 4
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
• 239000000080 wetting agent Substances 0.000 description 4
• WNQHCICGYPNPJA-DTORHVGOSA-N (3as,6ar)-5-(6-chloropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound C1=NC(Cl)=CC=C1N1C[C@H]2CNC[C@H]2C1 WNQHCICGYPNPJA-DTORHVGOSA-N 0.000 description 3
• KOMXDDRATCALPT-AOOOYVTPSA-N (3as,6ar)-5-pyridin-3-yl-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound C([C@H]1CNC[C@H]1C1)N1C1=CC=CN=C1 KOMXDDRATCALPT-AOOOYVTPSA-N 0.000 description 3
• YLTJVIIEHKBRPA-UHFFFAOYSA-N (6-aminopyridin-2-yl)-(1-methylpiperidin-4-yl)methanone Chemical compound C1CN(C)CCC1C(=O)C1=CC=CC(N)=N1 YLTJVIIEHKBRPA-UHFFFAOYSA-N 0.000 description 3
• QFCMBRXRVQRSSF-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropyrrolo[3,4-c]pyrrole Chemical compound C1NCC2CNCC21 QFCMBRXRVQRSSF-UHFFFAOYSA-N 0.000 description 3
• WPHUUIODWRNJLO-UHFFFAOYSA-N 2-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1S(Cl)(=O)=O WPHUUIODWRNJLO-UHFFFAOYSA-N 0.000 description 3
• FZWUIWQMJFAWJW-UHFFFAOYSA-N 3-bromo-5-methoxypyridine Chemical compound COC1=CN=CC(Br)=C1 FZWUIWQMJFAWJW-UHFFFAOYSA-N 0.000 description 3
• 208000030507 AIDS Diseases 0.000 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
• 208000019901 Anxiety disease Diseases 0.000 description 3
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
• 102000009660 Cholinergic Receptors Human genes 0.000 description 3
• 108010009685 Cholinergic Receptors Proteins 0.000 description 3
• 208000011231 Crohn disease Diseases 0.000 description 3
• 206010013654 Drug abuse Diseases 0.000 description 3
• 208000030814 Eating disease Diseases 0.000 description 3
• 208000010228 Erectile Dysfunction Diseases 0.000 description 3
• 208000019454 Feeding and Eating disease Diseases 0.000 description 3
• 206010061218 Inflammation Diseases 0.000 description 3
• 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 3
• 206010026749 Mania Diseases 0.000 description 3
• 208000019695 Migraine disease Diseases 0.000 description 3
• 206010036618 Premenstrual syndrome Diseases 0.000 description 3
• 241000700159 Rattus Species 0.000 description 3
• 206010046543 Urinary incontinence Diseases 0.000 description 3
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
• 239000002671 adjuvant Substances 0.000 description 3
• 235000010443 alginic acid Nutrition 0.000 description 3
• 229920000615 alginic acid Polymers 0.000 description 3
• 208000022531 anorexia Diseases 0.000 description 3
• 230000036506 anxiety Effects 0.000 description 3
• 230000008901 benefit Effects 0.000 description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
• 230000005540 biological transmission Effects 0.000 description 3
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 3
• 239000002775 capsule 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
• 238000002425 crystallisation Methods 0.000 description 3
• 230000008025 crystallization Effects 0.000 description 3
• 125000004122 cyclic group Chemical group 0.000 description 3
• 125000000753 cycloalkyl group Chemical group 0.000 description 3
• 238000000354 decomposition reaction Methods 0.000 description 3
• 206010061428 decreased appetite Diseases 0.000 description 3
• 235000014632 disordered eating Nutrition 0.000 description 3
• 239000006185 dispersion Substances 0.000 description 3
• 239000003995 emulsifying agent Substances 0.000 description 3
• 206010015037 epilepsy Diseases 0.000 description 3
• 229960002870 gabapentin Drugs 0.000 description 3
• 235000011187 glycerol Nutrition 0.000 description 3
• 125000005842 heteroatom Chemical group 0.000 description 3
• 238000004128 high performance liquid chromatography Methods 0.000 description 3
• 230000007062 hydrolysis Effects 0.000 description 3
• 238000006460 hydrolysis reaction Methods 0.000 description 3
• 201000001881 impotence Diseases 0.000 description 3
• 238000000338 in vitro Methods 0.000 description 3
• 230000002757 inflammatory effect Effects 0.000 description 3
• 230000004054 inflammatory process Effects 0.000 description 3
• 238000007912 intraperitoneal administration Methods 0.000 description 3
• 150000002500 ions Chemical class 0.000 description 3
• 230000007794 irritation Effects 0.000 description 3
• 239000008101 lactose Substances 0.000 description 3
• 150000002632 lipids Chemical class 0.000 description 3
• 238000005259 measurement Methods 0.000 description 3
• 230000001404 mediated effect Effects 0.000 description 3
• 206010027175 memory impairment Diseases 0.000 description 3
• 206010027599 migraine Diseases 0.000 description 3
• 229960005181 morphine Drugs 0.000 description 3
• RPZAAFUKDPKTKP-UHFFFAOYSA-N n-(methoxymethyl)-1-phenyl-n-(trimethylsilylmethyl)methanamine Chemical compound COCN(C[Si](C)(C)C)CC1=CC=CC=C1 RPZAAFUKDPKTKP-UHFFFAOYSA-N 0.000 description 3
• 210000005036 nerve Anatomy 0.000 description 3
• 230000004770 neurodegeneration Effects 0.000 description 3
• 230000004112 neuroprotection Effects 0.000 description 3
• 150000007524 organic acids Chemical class 0.000 description 3
• 239000012071 phase Substances 0.000 description 3
• 239000006187 pill Substances 0.000 description 3
• 229910052697 platinum Inorganic materials 0.000 description 3
• 238000002360 preparation method Methods 0.000 description 3
• 239000003755 preservative agent Substances 0.000 description 3
• 230000008569 process Effects 0.000 description 3
• 238000011160 research Methods 0.000 description 3
• 208000019116 sleep disease Diseases 0.000 description 3
• 230000005586 smoking cessation Effects 0.000 description 3
• 239000012279 sodium borohydride Substances 0.000 description 3
• 229910000033 sodium borohydride Inorganic materials 0.000 description 3
• 239000011780 sodium chloride Substances 0.000 description 3
• KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 3
• 229910000080 stannane Inorganic materials 0.000 description 3
• 239000011550 stock solution Substances 0.000 description 3
• 208000011117 substance-related disease Diseases 0.000 description 3
• 208000011580 syndromic disease Diseases 0.000 description 3
• 239000006188 syrup Substances 0.000 description 3
• 235000020357 syrup Nutrition 0.000 description 3
• 239000003826 tablet Substances 0.000 description 3
• 210000001519 tissue Anatomy 0.000 description 3
• 150000003613 toluenes Chemical class 0.000 description 3
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
• 229910052727 yttrium Inorganic materials 0.000 description 3
• PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
• UYIUNJSSOQVGBS-UONRGADFSA-N (1r,5r)-7-(6-chloropyridin-3-yl)-4,7-diazabicyclo[3.2.0]heptane;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.CC1=CC=C(S(O)(=O)=O)C=C1.C1=NC(Cl)=CC=C1N1[C@@H]2CCN[C@@H]2C1 UYIUNJSSOQVGBS-UONRGADFSA-N 0.000 description 2
• RQYLYBKBTQKNMZ-GMSGAONNSA-N (1r,5s)-6-(5-azidopyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound [N-]=[N+]=NC1=CN=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 RQYLYBKBTQKNMZ-GMSGAONNSA-N 0.000 description 2
• AXDUZGSNAQMXLT-AXQPOKSYSA-N (1r,5s)-6-(5-bromopyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.BrC1=CN=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 AXDUZGSNAQMXLT-AXQPOKSYSA-N 0.000 description 2
• WQKRIRSAUKKPKU-NKPZAKOOSA-N (1s,6r)-4-(6-chloropyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.CC1=CC=C(S(O)(=O)=O)C=C1.C1=NC(Cl)=CC=C1N1C[C@@H]2NC[C@@H]2CC1 WQKRIRSAUKKPKU-NKPZAKOOSA-N 0.000 description 2
• PXXBNOWYKAESNH-NKPZAKOOSA-N (1s,6r)-7-(6-chloropyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.CC1=CC=C(S(O)(=O)=O)C=C1.C1=NC(Cl)=CC=C1N1[C@H]2CNCC[C@H]2C1 PXXBNOWYKAESNH-NKPZAKOOSA-N 0.000 description 2
• JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
• NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
• HICHVKKXKFJWOW-QJVKKXMWSA-N (3ar,6ar)-5-(5,6-dichloropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole;hydrochloride Chemical compound Cl.N1=C(Cl)C(Cl)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 HICHVKKXKFJWOW-QJVKKXMWSA-N 0.000 description 2
• WZXVMYJSUYIOKU-IEQXMABBSA-N (3ar,6ar)-5-(5-bromopyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole;dihydrochloride Chemical compound Cl.Cl.BrC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 WZXVMYJSUYIOKU-IEQXMABBSA-N 0.000 description 2
• XWJWZQOEIQRJPI-FZIZHOOBSA-N (3ar,6ar)-5-(5-ethenylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole;dihydrochloride Chemical compound Cl.Cl.C=CC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 XWJWZQOEIQRJPI-FZIZHOOBSA-N 0.000 description 2
• VWVOQSIZVRDLRN-QVJGMPPOSA-N (3ar,6ar)-5-(5-methoxypyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole;dihydrochloride Chemical compound Cl.Cl.COC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 VWVOQSIZVRDLRN-QVJGMPPOSA-N 0.000 description 2
• RHKQJAYQDBHCHR-SFGLUTOSSA-N (3ar,6ar)-5-(6-bromo-5-methylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole;dihydrochloride Chemical compound Cl.Cl.N1=C(Br)C(C)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 RHKQJAYQDBHCHR-SFGLUTOSSA-N 0.000 description 2
• XBOWJZPWRVADDI-XQKZEKTMSA-N (3ar,6ar)-5-(6-chloro-5-methylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole;hydrochloride Chemical compound Cl.N1=C(Cl)C(C)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 XBOWJZPWRVADDI-XQKZEKTMSA-N 0.000 description 2
• KQHIAPDXGBAFSK-WAZPLGGWSA-N (3ar,6ar)-5-(6-chloropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole;dihydrochloride Chemical compound Cl.Cl.C1=NC(Cl)=CC=C1N1C[C@@H]2NCC[C@@H]2C1 KQHIAPDXGBAFSK-WAZPLGGWSA-N 0.000 description 2
• VPKHOFPOKYUPHH-SFGLUTOSSA-N (3ar,6ar)-5-pyridin-3-yl-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole;dihydrochloride Chemical compound Cl.Cl.C([C@H]1CCN[C@H]1C1)N1C1=CC=CN=C1 VPKHOFPOKYUPHH-SFGLUTOSSA-N 0.000 description 2
• GUZUKHDQICFNFX-PHIMTYICSA-N (3ar,6as)-5-(5-ethoxypyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound CCOC1=CN=CC(N2C[C@H]3CNC[C@H]3C2)=C1 GUZUKHDQICFNFX-PHIMTYICSA-N 0.000 description 2
• HICHVKKXKFJWOW-XQRIHRDZSA-N (3as,6as)-5-(5,6-dichloropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole;hydrochloride Chemical compound Cl.N1=C(Cl)C(Cl)=CC(N2C[C@H]3NCC[C@H]3C2)=C1 HICHVKKXKFJWOW-XQRIHRDZSA-N 0.000 description 2
• OXRWNXOEHVDHOX-IBYXRORRSA-N (3as,6as)-5-(5-bromopyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.BrC1=CN=CC(N2C[C@H]3NCC[C@H]3C2)=C1 OXRWNXOEHVDHOX-IBYXRORRSA-N 0.000 description 2
• XBOWJZPWRVADDI-QLSWKGBWSA-N (3as,6as)-5-(6-chloro-5-methylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole;hydrochloride Chemical compound Cl.N1=C(Cl)C(C)=CC(N2C[C@H]3NCC[C@H]3C2)=C1 XBOWJZPWRVADDI-QLSWKGBWSA-N 0.000 description 2
• KQHIAPDXGBAFSK-UQZKZZBYSA-N (3as,6as)-5-(6-chloropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole;dihydrochloride Chemical compound Cl.Cl.C1=NC(Cl)=CC=C1N1C[C@H]2NCC[C@H]2C1 KQHIAPDXGBAFSK-UQZKZZBYSA-N 0.000 description 2
• KZGZKDWLMIHZTD-QLSWKGBWSA-N (3as,6as)-5-pyridin-3-yl-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.C([C@@H]1CCN[C@@H]1C1)N1C1=CC=CN=C1 KZGZKDWLMIHZTD-QLSWKGBWSA-N 0.000 description 2
• HJMWZYIKOPVUFB-UHFFFAOYSA-N (4-chlorophenyl)-piperidin-1-yldiazene Chemical compound C1=CC(Cl)=CC=C1N=NN1CCCCC1 HJMWZYIKOPVUFB-UHFFFAOYSA-N 0.000 description 2
• BMQCGDUOAYFWIO-RPWWDZGESA-N (e)-but-2-enedioic acid;(1r,6s)-7-(6-chloropyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound OC(=O)\C=C\C(O)=O.OC(=O)\C=C\C(O)=O.C1=NC(Cl)=CC=C1N1[C@@H]2CNCC[C@@H]2C1 BMQCGDUOAYFWIO-RPWWDZGESA-N 0.000 description 2
• ZPAUUYOZUOKYRA-FTZFTMOLSA-N (e)-but-2-enedioic acid;(1s,5r)-6-(6-chloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound OC(=O)\C=C\C(O)=O.C1=NC(Cl)=CC=C1N1[C@H]2CNC[C@H]2C1 ZPAUUYOZUOKYRA-FTZFTMOLSA-N 0.000 description 2
• NTYRHVKKVDBMKC-XXKWJKJXSA-N (e)-but-2-enedioic acid;(1s,5r)-6-pyridin-3-yl-3,6-diazabicyclo[3.2.0]heptane Chemical compound OC(=O)\C=C\C(O)=O.N1([C@H]2CNC[C@H]2C1)C1=CC=CN=C1 NTYRHVKKVDBMKC-XXKWJKJXSA-N 0.000 description 2
• YKXHWBLCEXDOCR-JBECICKSSA-N (e)-but-2-enedioic acid;(1s,5s)-3-(6-chloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound OC(=O)\C=C\C(O)=O.C1=NC(Cl)=CC=C1N1C[C@H]2NC[C@H]2C1 YKXHWBLCEXDOCR-JBECICKSSA-N 0.000 description 2
• INZFROXUUYJFTB-XXKWJKJXSA-N (e)-but-2-enedioic acid;(1s,6r)-4-(6-chloropyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound OC(=O)\C=C\C(O)=O.C1=NC(Cl)=CC=C1N1C[C@@H]2NC[C@@H]2CC1 INZFROXUUYJFTB-XXKWJKJXSA-N 0.000 description 2
• PASKJJGPVQGRTN-BNEOOWBWSA-N (e)-but-2-enedioic acid;5-[(1s,6r)-4,7-diazabicyclo[4.2.0]octan-7-yl]pyridine-3-carbonitrile Chemical compound OC(=O)\C=C\C(O)=O.N#CC1=CN=CC(N2[C@H]3CNCC[C@H]3C2)=C1 PASKJJGPVQGRTN-BNEOOWBWSA-N 0.000 description 2
• OZTPQWRLHLQVBD-UHFFFAOYSA-N 1,2,3,4-tetrahydro-2,7-naphthyridine Chemical compound C1=NC=C2CNCCC2=C1 OZTPQWRLHLQVBD-UHFFFAOYSA-N 0.000 description 2
• VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
• 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 2
• XSHFSZAXOOQKQS-UHFFFAOYSA-N 2,3-dichloro-5-iodopyridine Chemical compound ClC1=CC(I)=CN=C1Cl XSHFSZAXOOQKQS-UHFFFAOYSA-N 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• YVFKDAIIAXSEFK-UHFFFAOYSA-N 2-amino-3-(2-aminoethyl)hexanedioic acid Chemical compound NCCC(C(N)C(O)=O)CCC(O)=O YVFKDAIIAXSEFK-UHFFFAOYSA-N 0.000 description 2
• IMYYCZADDHYKLF-UHFFFAOYSA-N 2-azaniumyl-2-(4-hydroxycyclohexyl)acetate Chemical compound OC(=O)C(N)C1CCC(O)CC1 IMYYCZADDHYKLF-UHFFFAOYSA-N 0.000 description 2
• RLHRYJJOKQQNFP-UHFFFAOYSA-N 2-benzamido-2-(4-oxocyclohexyl)acetic acid Chemical compound C1CC(=O)CCC1C(C(=O)O)NC(=O)C1=CC=CC=C1 RLHRYJJOKQQNFP-UHFFFAOYSA-N 0.000 description 2
• LSSPXHUYLWXIIH-UHFFFAOYSA-N 2-benzamido-2-(7-oxoazepan-4-yl)acetic acid Chemical compound C1CNC(=O)CCC1C(C(=O)O)NC(=O)C1=CC=CC=C1 LSSPXHUYLWXIIH-UHFFFAOYSA-N 0.000 description 2
• YOWQWFMSQCOSBA-UHFFFAOYSA-N 2-methoxypropene Chemical compound COC(C)=C YOWQWFMSQCOSBA-UHFFFAOYSA-N 0.000 description 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
• JMTMWFZXOIWTLX-UHFFFAOYSA-N 2-pyridin-2-yloxypyridine Chemical class C=1C=CC=NC=1OC1=CC=CC=N1 JMTMWFZXOIWTLX-UHFFFAOYSA-N 0.000 description 2
• YSHKYZAWTWKQKK-UHFFFAOYSA-N 3-bromo-5-phenylmethoxypyridine Chemical compound BrC1=CN=CC(OCC=2C=CC=CC=2)=C1 YSHKYZAWTWKQKK-UHFFFAOYSA-N 0.000 description 2
• 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
• 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 2
• REODJSKVYHWCRS-HSTMFJOWSA-N 4-methylbenzenesulfonic acid;(1r,5r)-4-pyridin-3-yl-4,7-diazabicyclo[3.2.0]heptane Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.CC1=CC=C(S(O)(=O)=O)C=C1.C([C@H]1NC[C@@H]21)CN2C1=CC=CN=C1 REODJSKVYHWCRS-HSTMFJOWSA-N 0.000 description 2
• ZOIXFSXGAIVUID-HSTMFJOWSA-N 4-methylbenzenesulfonic acid;(1r,5r)-7-pyridin-3-yl-4,7-diazabicyclo[3.2.0]heptane Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.CC1=CC=C(S(O)(=O)=O)C=C1.N1([C@@H]2CCN[C@@H]2C1)C1=CC=CN=C1 ZOIXFSXGAIVUID-HSTMFJOWSA-N 0.000 description 2
• HIOWHTOPHCHYGG-UQZKZZBYSA-N 4-methylbenzenesulfonic acid;(1s,5s)-3-pyridin-3-yl-3,6-diazabicyclo[3.2.0]heptane Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.CC1=CC=C(S(O)(=O)=O)C=C1.C([C@H]1NC[C@H]1C1)N1C1=CC=CN=C1 HIOWHTOPHCHYGG-UQZKZZBYSA-N 0.000 description 2
• VUUFVZBBGWQHDJ-NZHTYBOASA-N 4-methylbenzenesulfonic acid;(1s,6r)-7-pyridin-3-yl-4,7-diazabicyclo[4.2.0]octane Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.CC1=CC=C(S(O)(=O)=O)C=C1.N1([C@H]2CNCC[C@H]2C1)C1=CC=CN=C1 VUUFVZBBGWQHDJ-NZHTYBOASA-N 0.000 description 2
• QUTYKIXIUDQOLK-PRJMDXOYSA-N 5-O-(1-carboxyvinyl)-3-phosphoshikimic acid Chemical compound O[C@H]1[C@H](OC(=C)C(O)=O)CC(C(O)=O)=C[C@H]1OP(O)(O)=O QUTYKIXIUDQOLK-PRJMDXOYSA-N 0.000 description 2
• SIJUVFFCMJGCMM-DQNKZQNQSA-N 5-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-2-bromopyridine-3-carbonitrile;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.C1=C(C#N)C(Br)=NC=C1N1C[C@@H]2NCC[C@@H]2C1 SIJUVFFCMJGCMM-DQNKZQNQSA-N 0.000 description 2
• FTFFHWWIPOQCBC-UHFFFAOYSA-N 5-bromopyridine-3-carbonitrile Chemical compound BrC1=CN=CC(C#N)=C1 FTFFHWWIPOQCBC-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 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 2
• 229920001817 Agar Polymers 0.000 description 2
• 101100477360 Arabidopsis thaliana IPSP gene Proteins 0.000 description 2
• BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
• SABNXZGXKJUVBC-HCGIDSDESA-N CC1=CC=C(S(O)(=O)=O)C=C1.CC1=CC=C(S(O)(=O)=O)C=C1.CC1=CC=C(S(O)(=O)=O)C=C1.C([C@@H]1NC[C@@H]1CC1)N1C1=CC=CN=C1 Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.CC1=CC=C(S(O)(=O)=O)C=C1.CC1=CC=C(S(O)(=O)=O)C=C1.C([C@@H]1NC[C@@H]1CC1)N1C1=CC=CN=C1 SABNXZGXKJUVBC-HCGIDSDESA-N 0.000 description 2
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
• 239000004215 Carbon black (E152) Substances 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
• TZULSCLUWZPFLT-VWXHXBRYSA-N Cl.Cl.C([C@@H]1CCN[C@@H]1C1)CN1C1=CC=CN=C1 Chemical compound Cl.Cl.C([C@@H]1CCN[C@@H]1C1)CN1C1=CC=CN=C1 TZULSCLUWZPFLT-VWXHXBRYSA-N 0.000 description 2
• PUEVTTMNTBHYQJ-TZTYKVLHSA-N Cl.Cl.Cl.CC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 Chemical compound Cl.Cl.Cl.CC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 PUEVTTMNTBHYQJ-TZTYKVLHSA-N 0.000 description 2
• 241000557626 Corvus corax Species 0.000 description 2
• ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 2
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
• 108010010803 Gelatin Proteins 0.000 description 2
• 241000282412 Homo Species 0.000 description 2
• KOTOUBGHZHWCCJ-UHFFFAOYSA-N IPSP Chemical compound CCS(=O)CSP(=S)(OC(C)C)OC(C)C KOTOUBGHZHWCCJ-UHFFFAOYSA-N 0.000 description 2
• PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• 241000699666 Mus <mouse, genus> Species 0.000 description 2
• PSDCLIQUBHYQIP-UHFFFAOYSA-N N=1C(C=CC2=CC=NC(C=12)=O)=O Chemical compound N=1C(C=CC2=CC=NC(C=12)=O)=O PSDCLIQUBHYQIP-UHFFFAOYSA-N 0.000 description 2
• 244000061176 Nicotiana tabacum Species 0.000 description 2
• 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
• 229910019142 PO4 Inorganic materials 0.000 description 2
• 244000025272 Persea americana Species 0.000 description 2
• 235000008673 Persea americana Nutrition 0.000 description 2
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
• 239000002202 Polyethylene glycol Substances 0.000 description 2
• 102000004659 Presynaptic Receptors Human genes 0.000 description 2
• 108010003717 Presynaptic Receptors Proteins 0.000 description 2
• IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• 229920002472 Starch Polymers 0.000 description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 229960001138 acetylsalicylic acid Drugs 0.000 description 2
• 230000036982 action potential Effects 0.000 description 2
• 230000004913 activation Effects 0.000 description 2
• 230000010933 acylation Effects 0.000 description 2
• 238000005917 acylation reaction Methods 0.000 description 2
• 239000008272 agar Substances 0.000 description 2
• 239000000556 agonist Substances 0.000 description 2
• 229940072056 alginate Drugs 0.000 description 2
• 150000001336 alkenes Chemical class 0.000 description 2
• 150000001345 alkine derivatives Chemical class 0.000 description 2
• 230000029936 alkylation Effects 0.000 description 2
• 238000005804 alkylation reaction Methods 0.000 description 2
• 208000026935 allergic disease Diseases 0.000 description 2
• 150000001408 amides Chemical class 0.000 description 2
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
• 229910021529 ammonia Inorganic materials 0.000 description 2
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 2
• 230000003502 anti-nociceptive effect Effects 0.000 description 2
• 229940125681 anticonvulsant agent Drugs 0.000 description 2
• HJJPJSXJAXAIPN-UHFFFAOYSA-N arecoline Chemical compound COC(=O)C1=CCCN(C)C1 HJJPJSXJAXAIPN-UHFFFAOYSA-N 0.000 description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
• DXZDEAJXVCLRLE-UHFFFAOYSA-N azepin-2-one Chemical compound O=C1C=CC=CC=N1 DXZDEAJXVCLRLE-UHFFFAOYSA-N 0.000 description 2
• 230000006399 behavior Effects 0.000 description 2
• 230000003542 behavioural effect Effects 0.000 description 2
• 239000000440 bentonite Substances 0.000 description 2
• 229910000278 bentonite Inorganic materials 0.000 description 2
• SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
• ZLTOMYVCMSDSRD-GDBMZVCRSA-N benzyl (1s,5s)-6-(6-chloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate Chemical compound C1=NC(Cl)=CC=C1N1[C@@H]2CN(C(=O)OCC=3C=CC=CC=3)C[C@@H]2C1 ZLTOMYVCMSDSRD-GDBMZVCRSA-N 0.000 description 2
• JUZMKGYDAATEET-NVXWUHKLSA-N benzyl (1s,5s)-6-pyridin-3-yl-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate Chemical compound C([C@H]1N(C[C@H]1C1)C=2C=NC=CC=2)N1C(=O)OCC1=CC=CC=C1 JUZMKGYDAATEET-NVXWUHKLSA-N 0.000 description 2
• HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
• 125000002619 bicyclic group Chemical group 0.000 description 2
• 230000027455 binding Effects 0.000 description 2
• 239000011230 binding agent Substances 0.000 description 2
• 229920002988 biodegradable polymer Polymers 0.000 description 2
• 239000004621 biodegradable polymer Substances 0.000 description 2
• 230000033228 biological regulation Effects 0.000 description 2
• 229910052799 carbon Inorganic materials 0.000 description 2
• 230000003197 catalytic effect Effects 0.000 description 2
• 239000003638 chemical reducing agent Substances 0.000 description 2
• OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
• 238000000576 coating method 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
• 230000003111 delayed effect Effects 0.000 description 2
• 150000002009 diols Chemical class 0.000 description 2
• 239000002552 dosage form Substances 0.000 description 2
• 238000010828 elution Methods 0.000 description 2
• 239000000839 emulsion Substances 0.000 description 2
• 238000001704 evaporation Methods 0.000 description 2
• 230000008020 evaporation Effects 0.000 description 2
• 239000000945 filler Substances 0.000 description 2
• 239000008273 gelatin Substances 0.000 description 2
• 229920000159 gelatin Polymers 0.000 description 2
• 235000019322 gelatine Nutrition 0.000 description 2
• 235000011852 gelatine desserts Nutrition 0.000 description 2
• 239000008187 granular material Substances 0.000 description 2
• 210000002064 heart cell Anatomy 0.000 description 2
• XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
• BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
• 229930195733 hydrocarbon Natural products 0.000 description 2
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
• 238000011065 in-situ storage Methods 0.000 description 2
• 239000003701 inert diluent Substances 0.000 description 2
• 230000005764 inhibitory process Effects 0.000 description 2
• 238000007689 inspection Methods 0.000 description 2
• 230000003993 interaction Effects 0.000 description 2
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
• 238000002955 isolation Methods 0.000 description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
• 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 2
• 239000000787 lecithin Substances 0.000 description 2
• 235000010445 lecithin Nutrition 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
• 238000004519 manufacturing process Methods 0.000 description 2
• 239000011159 matrix material Substances 0.000 description 2
• IBIKHMZPHNKTHM-RDTXWAMCSA-N merck compound 25 Chemical compound C1C[C@@H](C(O)=O)[C@H](O)CN1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CC1 IBIKHMZPHNKTHM-RDTXWAMCSA-N 0.000 description 2
• 150000007522 mineralic acids Chemical class 0.000 description 2
• 230000037230 mobility Effects 0.000 description 2
• 125000002950 monocyclic group Chemical group 0.000 description 2
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• 210000001640 nerve ending Anatomy 0.000 description 2
• 210000002569 neuron Anatomy 0.000 description 2
• 238000006386 neutralization reaction Methods 0.000 description 2
• 150000002825 nitriles Chemical class 0.000 description 2
• 239000002674 ointment Substances 0.000 description 2
• 239000004006 olive oil Substances 0.000 description 2
• 235000008390 olive oil Nutrition 0.000 description 2
• 210000003463 organelle Anatomy 0.000 description 2
• 235000005985 organic acids Nutrition 0.000 description 2
• 125000001979 organolithium group Chemical group 0.000 description 2
• 229910052760 oxygen Inorganic materials 0.000 description 2
• 239000001301 oxygen Substances 0.000 description 2
• 230000000144 pharmacologic effect Effects 0.000 description 2
• 235000021317 phosphate Nutrition 0.000 description 2
• 150000003904 phospholipids Chemical class 0.000 description 2
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
• 230000001766 physiological effect Effects 0.000 description 2
• 229960005235 piperonyl butoxide Drugs 0.000 description 2
• 229920000642 polymer Polymers 0.000 description 2
• AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 description 2
• 229960001233 pregabalin Drugs 0.000 description 2
• 238000001953 recrystallisation Methods 0.000 description 2
• 230000004044 response Effects 0.000 description 2
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
• 210000002027 skeletal muscle Anatomy 0.000 description 2
• 208000020685 sleep-wake disease Diseases 0.000 description 2
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
• 239000012312 sodium hydride Substances 0.000 description 2
• 229910000104 sodium hydride Inorganic materials 0.000 description 2
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
• 239000007909 solid dosage form Substances 0.000 description 2
• 239000008247 solid mixture Substances 0.000 description 2
• 239000003381 stabilizer Substances 0.000 description 2
• 235000019698 starch Nutrition 0.000 description 2
• KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
• 235000000346 sugar Nutrition 0.000 description 2
• 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
• 229940124530 sulfonamide Drugs 0.000 description 2
• 150000003456 sulfonamides Chemical class 0.000 description 2
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
• 230000006103 sulfonylation Effects 0.000 description 2
• 238000005694 sulfonylation reaction Methods 0.000 description 2
• 239000011593 sulfur Substances 0.000 description 2
• 239000000829 suppository Substances 0.000 description 2
• 239000000375 suspending agent Substances 0.000 description 2
• 210000002182 synaptic membrane Anatomy 0.000 description 2
• LRCPRHFAAYJMHG-RKDXNWHRSA-N tert-butyl (3s,4s)-3-amino-4-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@H](CO)[C@H](N)C1 LRCPRHFAAYJMHG-RKDXNWHRSA-N 0.000 description 2
• HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
• 238000002560 therapeutic procedure Methods 0.000 description 2
• 238000011200 topical administration Methods 0.000 description 2
• 230000001988 toxicity Effects 0.000 description 2
• 231100000419 toxicity Toxicity 0.000 description 2
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
• 239000003981 vehicle Substances 0.000 description 2
• 239000003039 volatile agent Substances 0.000 description 2
• 239000001993 wax Substances 0.000 description 2
• 239000008096 xylene Substances 0.000 description 2
• GXFZCDMWGMFGFL-KKXMJGKMSA-N (+)-Tubocurarine chloride hydrochloride Chemical compound [Cl-].[Cl-].C([C@H]1[N+](C)(C)CCC=2C=C(C(=C(OC3=CC=C(C=C3)C[C@H]3C=4C=C(C(=CC=4CC[NH+]3C)OC)O3)C=21)O)OC)C1=CC=C(O)C3=C1 GXFZCDMWGMFGFL-KKXMJGKMSA-N 0.000 description 1
• LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
• RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 description 1
• RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 description 1
• YCEMQEOVBUUXAV-VXGBXAGGSA-N (1r,5r)-7-benzyl-4,7-diazabicyclo[3.2.0]heptane Chemical compound N1([C@@H]2CCN[C@@H]2C1)CC1=CC=CC=C1 YCEMQEOVBUUXAV-VXGBXAGGSA-N 0.000 description 1
• XXPJARVZQPEZNZ-IAGOWNOFSA-N (1r,5r)-7-benzyl-4-pyridin-3-yl-4,7-diazabicyclo[3.2.0]heptane Chemical compound C([C@@H]1[C@H]2CN1CC=1C=CC=CC=1)CN2C1=CC=CN=C1 XXPJARVZQPEZNZ-IAGOWNOFSA-N 0.000 description 1
• XLWRHIFAGPGATJ-NXEZZACHSA-N (1r,5r)-7-pyridin-3-yl-4,7-diazabicyclo[3.2.0]heptane Chemical compound N1([C@@H]2CCN[C@@H]2C1)C1=CC=CN=C1 XLWRHIFAGPGATJ-NXEZZACHSA-N 0.000 description 1
• LPHNATBYCLFLSS-GMSGAONNSA-N (1r,5s)-6-(5-fluoropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound FC1=CN=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 LPHNATBYCLFLSS-GMSGAONNSA-N 0.000 description 1
• IHJRTAKNNJCUEJ-HZGVNTEJSA-N (1r,5s)-6-(6-chloro-5-fluoropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1=C(Cl)C(F)=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 IHJRTAKNNJCUEJ-HZGVNTEJSA-N 0.000 description 1
• IJZBDKKZKRRESD-MWLCHTKSSA-N (1r,5s)-6-(6-methylpyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound C1=NC(C)=CC=C1N1[C@@H]2CNC[C@@H]2C1 IJZBDKKZKRRESD-MWLCHTKSSA-N 0.000 description 1
• WYMGCHPOMQGPPC-GMSGAONNSA-N (1r,6r)-8-(5,6-dichloropyridin-3-yl)-4,8-diazabicyclo[4.2.0]octane Chemical compound N1=C(Cl)C(Cl)=CC(N2[C@@H]3CCNC[C@@H]3C2)=C1 WYMGCHPOMQGPPC-GMSGAONNSA-N 0.000 description 1
• DLRFLULJVWWCSZ-LDYMZIIASA-N (1r,6r)-8-(5-fluoropyridin-3-yl)-4,8-diazabicyclo[4.2.0]octane Chemical compound FC1=CN=CC(N2[C@@H]3CCNC[C@@H]3C2)=C1 DLRFLULJVWWCSZ-LDYMZIIASA-N 0.000 description 1
• JWSLQARRYMGCLR-GMSGAONNSA-N (1r,6r)-8-(6-chloro-5-fluoropyridin-3-yl)-4,8-diazabicyclo[4.2.0]octane Chemical compound N1=C(Cl)C(F)=CC(N2[C@@H]3CCNC[C@@H]3C2)=C1 JWSLQARRYMGCLR-GMSGAONNSA-N 0.000 description 1
• GJTHFVDGFBSCBN-MWLCHTKSSA-N (1r,6r)-8-(6-chloro-5-methylpyridin-3-yl)-4,8-diazabicyclo[4.2.0]octane Chemical compound N1=C(Cl)C(C)=CC(N2[C@@H]3CCNC[C@@H]3C2)=C1 GJTHFVDGFBSCBN-MWLCHTKSSA-N 0.000 description 1
• WWYKDUOHHPBKIY-PSASIEDQSA-N (1r,6r)-8-(6-chloropyridin-3-yl)-4,8-diazabicyclo[4.2.0]octane Chemical compound C1=NC(Cl)=CC=C1N1[C@@H]2CCNC[C@@H]2C1 WWYKDUOHHPBKIY-PSASIEDQSA-N 0.000 description 1
• WIXKDPXGNKHZCO-ZYHUDNBSSA-N (1r,6r)-8-(6-methylpyridin-3-yl)-4,8-diazabicyclo[4.2.0]octane Chemical compound C1=NC(C)=CC=C1N1[C@@H]2CCNC[C@@H]2C1 WIXKDPXGNKHZCO-ZYHUDNBSSA-N 0.000 description 1
• QJFNVWSQRAPGRC-MWLCHTKSSA-N (1r,6r)-8-pyridin-3-yl-4,8-diazabicyclo[4.2.0]octane Chemical compound N1([C@@H]2CCNC[C@@H]2C1)C1=CC=CN=C1 QJFNVWSQRAPGRC-MWLCHTKSSA-N 0.000 description 1
• QCYBDVYWRLOUDA-LDYMZIIASA-N (1r,7r)-4-(5,6-dichloropyridin-3-yl)-4,8-diazabicyclo[5.2.0]nonane Chemical compound N1=C(Cl)C(Cl)=CC(N2CC[C@H]3NC[C@H]3CC2)=C1 QCYBDVYWRLOUDA-LDYMZIIASA-N 0.000 description 1
• DEVIIHJYELEBMM-BXKDBHETSA-N (1r,7r)-4-(5-fluoropyridin-3-yl)-4,8-diazabicyclo[5.2.0]nonane Chemical compound FC1=CN=CC(N2CC[C@H]3NC[C@H]3CC2)=C1 DEVIIHJYELEBMM-BXKDBHETSA-N 0.000 description 1
• YJUZQSBUSFLCKS-LDYMZIIASA-N (1r,7r)-4-(6-chloro-5-fluoropyridin-3-yl)-4,8-diazabicyclo[5.2.0]nonane Chemical compound N1=C(Cl)C(F)=CC(N2CC[C@H]3NC[C@H]3CC2)=C1 YJUZQSBUSFLCKS-LDYMZIIASA-N 0.000 description 1
• KJFVHLQKCFXUGR-ZYHUDNBSSA-N (1r,7r)-4-(6-chloro-5-methylpyridin-3-yl)-4,8-diazabicyclo[5.2.0]nonane Chemical compound N1=C(Cl)C(C)=CC(N2CC[C@H]3NC[C@H]3CC2)=C1 KJFVHLQKCFXUGR-ZYHUDNBSSA-N 0.000 description 1
• CRESACQLOFWVCM-MWLCHTKSSA-N (1r,7r)-4-(6-chloropyridin-3-yl)-4,8-diazabicyclo[5.2.0]nonane Chemical compound C1=NC(Cl)=CC=C1N1CC[C@H]2NC[C@H]2CC1 CRESACQLOFWVCM-MWLCHTKSSA-N 0.000 description 1
• FBSVUZOBEZCQNO-DGCLKSJQSA-N (1r,7r)-4-(6-methylpyridin-3-yl)-4,8-diazabicyclo[5.2.0]nonane Chemical compound C1=NC(C)=CC=C1N1CC[C@H]2NC[C@H]2CC1 FBSVUZOBEZCQNO-DGCLKSJQSA-N 0.000 description 1
• SZCLDOIFQHFHCT-ZYHUDNBSSA-N (1r,7r)-4-pyridin-3-yl-4,8-diazabicyclo[5.2.0]nonane Chemical compound C([C@H]1NC[C@H]1CC1)CN1C1=CC=CN=C1 SZCLDOIFQHFHCT-ZYHUDNBSSA-N 0.000 description 1
• OGULMRQWNAMFPB-XVKPBYJWSA-N (1s,5r)-6-(5-bromopyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound BrC1=CN=CC(N2[C@H]3CNC[C@H]3C2)=C1 OGULMRQWNAMFPB-XVKPBYJWSA-N 0.000 description 1
• BWQKEWGYFNUHHX-CBAPKCEASA-N (1s,5r)-6-(6-bromo-5-methoxypyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1=C(Br)C(OC)=CC(N2[C@H]3CNC[C@H]3C2)=C1 BWQKEWGYFNUHHX-CBAPKCEASA-N 0.000 description 1
• NKPTYRUOSBCXRH-OIBJUYFYSA-N (1s,5s)-3-(5-fluoropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound FC1=CN=CC(N2C[C@H]3NC[C@H]3C2)=C1 NKPTYRUOSBCXRH-OIBJUYFYSA-N 0.000 description 1
• CRMZRQMQANKWHE-IMTBSYHQSA-N (1s,5s)-3-(6-chloro-5-fluoropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1=C(Cl)C(F)=CC(N2C[C@H]3NC[C@H]3C2)=C1 CRMZRQMQANKWHE-IMTBSYHQSA-N 0.000 description 1
• IGIZQHWJMCRTGE-WCBMZHEXSA-N (1s,5s)-3-(6-chloro-5-methylpyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1=C(Cl)C(C)=CC(N2C[C@H]3NC[C@H]3C2)=C1 IGIZQHWJMCRTGE-WCBMZHEXSA-N 0.000 description 1
• IJXOAWKUNFLXFM-GXSJLCMTSA-N (1s,5s)-3-(6-methylpyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound C1=NC(C)=CC=C1N1C[C@H]2NC[C@H]2C1 IJXOAWKUNFLXFM-GXSJLCMTSA-N 0.000 description 1
• PDNPYVGEHRTDKO-XVKPBYJWSA-N (1s,6r)-4-(5,6-dichloropyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound N1=C(Cl)C(Cl)=CC(N2C[C@@H]3NC[C@@H]3CC2)=C1 PDNPYVGEHRTDKO-XVKPBYJWSA-N 0.000 description 1
• VRIYWCYUXQMBTC-JQWIXIFHSA-N (1s,6r)-4-(5-methylpyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound CC1=CN=CC(N2C[C@@H]3NC[C@@H]3CC2)=C1 VRIYWCYUXQMBTC-JQWIXIFHSA-N 0.000 description 1
• PMXNVFZCROFMMO-XVKPBYJWSA-N (1s,6r)-4-(6-chloro-5-fluoropyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound N1=C(Cl)C(F)=CC(N2C[C@@H]3NC[C@@H]3CC2)=C1 PMXNVFZCROFMMO-XVKPBYJWSA-N 0.000 description 1
• NYHCAFZZTFTEHK-ONGXEEELSA-N (1s,6r)-4-(6-chloro-5-methylpyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound N1=C(Cl)C(C)=CC(N2C[C@@H]3NC[C@@H]3CC2)=C1 NYHCAFZZTFTEHK-ONGXEEELSA-N 0.000 description 1
• SFZROGZKWMLIIO-JQWIXIFHSA-N (1s,6r)-4-(6-methylpyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound C1=NC(C)=CC=C1N1C[C@@H]2NC[C@@H]2CC1 SFZROGZKWMLIIO-JQWIXIFHSA-N 0.000 description 1
• RAPANLXWTPJZKU-KWQFWETISA-N (1s,6r)-7-(5-fluoropyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound FC1=CN=CC(N2[C@H]3CNCC[C@H]3C2)=C1 RAPANLXWTPJZKU-KWQFWETISA-N 0.000 description 1
• MIYKMZBHGJTGHB-XVKPBYJWSA-N (1s,6r)-7-(6-chloro-5-fluoropyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound N1=C(Cl)C(F)=CC(N2[C@H]3CNCC[C@H]3C2)=C1 MIYKMZBHGJTGHB-XVKPBYJWSA-N 0.000 description 1
• KWGMTUKJOCWDBH-JQWIXIFHSA-N (1s,6r)-7-(6-methylpyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound C1=NC(C)=CC=C1N1[C@H]2CNCC[C@H]2C1 KWGMTUKJOCWDBH-JQWIXIFHSA-N 0.000 description 1
• VFBIVKIYFDEEFE-QNTKWALQSA-N (1s,6r)-7-benzyl-4,7-diazabicyclo[4.2.0]octane;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.N1([C@H]2CNCC[C@H]2C1)CC1=CC=CC=C1 VFBIVKIYFDEEFE-QNTKWALQSA-N 0.000 description 1
• LVKODCKNVBBJSA-WMZOPIPTSA-N (1s,6r)-7-benzyl-4-pyridin-3-yl-4,7-diazabicyclo[4.2.0]octane Chemical compound C([C@H]1CN([C@H]1C1)CC=2C=CC=CC=2)CN1C1=CC=CN=C1 LVKODCKNVBBJSA-WMZOPIPTSA-N 0.000 description 1
• AMXTXSUKEIIVAW-KWQFWETISA-N (1s,7r)-5-(5,6-dichloropyridin-3-yl)-5,8-diazabicyclo[5.2.0]nonane Chemical compound N1=C(Cl)C(Cl)=CC(N2C[C@@H]3NC[C@@H]3CCC2)=C1 AMXTXSUKEIIVAW-KWQFWETISA-N 0.000 description 1
• GOMDSULKVXSPNX-CABZTGNLSA-N (1s,7r)-5-(5-fluoropyridin-3-yl)-5,8-diazabicyclo[5.2.0]nonane Chemical compound FC1=CN=CC(N2C[C@@H]3NC[C@@H]3CCC2)=C1 GOMDSULKVXSPNX-CABZTGNLSA-N 0.000 description 1
• FLUPOMDKNWPKQI-KWQFWETISA-N (1s,7r)-5-(6-chloro-5-fluoropyridin-3-yl)-5,8-diazabicyclo[5.2.0]nonane Chemical compound N1=C(Cl)C(F)=CC(N2C[C@@H]3NC[C@@H]3CCC2)=C1 FLUPOMDKNWPKQI-KWQFWETISA-N 0.000 description 1
• QLCHEHPORVLLIS-JQWIXIFHSA-N (1s,7r)-5-(6-chloro-5-methylpyridin-3-yl)-5,8-diazabicyclo[5.2.0]nonane Chemical compound N1=C(Cl)C(C)=CC(N2C[C@@H]3NC[C@@H]3CCC2)=C1 QLCHEHPORVLLIS-JQWIXIFHSA-N 0.000 description 1
• MODMHOBWFCOZDT-ONGXEEELSA-N (1s,7r)-5-(6-chloropyridin-3-yl)-5,8-diazabicyclo[5.2.0]nonane Chemical compound C1=NC(Cl)=CC=C1N1C[C@@H]2NC[C@@H]2CCC1 MODMHOBWFCOZDT-ONGXEEELSA-N 0.000 description 1
• DBZXVWMYIVWMAE-AAEUAGOBSA-N (1s,7r)-5-(6-methylpyridin-3-yl)-5,8-diazabicyclo[5.2.0]nonane Chemical compound C1=NC(C)=CC=C1N1C[C@@H]2NC[C@@H]2CCC1 DBZXVWMYIVWMAE-AAEUAGOBSA-N 0.000 description 1
• DBYFOXPUXHKGDD-JQWIXIFHSA-N (1s,7r)-5-pyridin-3-yl-5,8-diazabicyclo[5.2.0]nonane Chemical compound C([C@@H]1NC[C@@H]1CCC1)N1C1=CC=CN=C1 DBYFOXPUXHKGDD-JQWIXIFHSA-N 0.000 description 1
• JLDHXHPQMBNKMC-BQBZGAKWSA-N (2s,3s)-3-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CC[C@H](O)[C@H]1C(O)=O JLDHXHPQMBNKMC-BQBZGAKWSA-N 0.000 description 1
• BYDOZJQQICNGSG-BNOWGMLFSA-N (3ar,6ar)-1-[(1r)-1-phenylethyl]-3,3a,4,5,6,6a-hexahydro-2h-pyrrolo[3,4-b]pyrrole Chemical compound C1([C@H](N2[C@H]3CNC[C@H]3CC2)C)=CC=CC=C1 BYDOZJQQICNGSG-BNOWGMLFSA-N 0.000 description 1
• LODPYENASSOOBD-OLZOCXBDSA-N (3ar,6ar)-1-benzyl-3,3a,4,5,6,6a-hexahydro-2h-pyrrolo[2,3-c]pyrrole Chemical compound N1([C@H]2CNC[C@H]2CC1)CC1=CC=CC=C1 LODPYENASSOOBD-OLZOCXBDSA-N 0.000 description 1
• NCSDFKQTTXROLF-MDYRTPRTSA-N (3ar,6ar)-5-(4-nitrophenyl)sulfonyl-1-[(1r)-1-phenylethyl]-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole Chemical compound C([C@H]1CCN([C@H]1C1)[C@H](C)C=2C=CC=CC=2)N1S(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 NCSDFKQTTXROLF-MDYRTPRTSA-N 0.000 description 1
• JKMYLFCKBHONIF-BVIGSMAQSA-N (3ar,6ar)-5-(6-bromo-5-chloropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.N1=C(Br)C(Cl)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 JKMYLFCKBHONIF-BVIGSMAQSA-N 0.000 description 1
• DWTZVDYZXFFTFH-SKDRFNHKSA-N (3ar,6ar)-5-[6-bromo-5-(methoxymethyl)pyridin-3-yl]-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound N1=C(Br)C(COC)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 DWTZVDYZXFFTFH-SKDRFNHKSA-N 0.000 description 1
• UBQWFBOLOFJCDH-PHIMTYICSA-N (3ar,6as)-2-methyl-5-pyridin-3-yl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole Chemical compound C([C@@H]1CN(C[C@@H]1C1)C)N1C1=CC=CN=C1 UBQWFBOLOFJCDH-PHIMTYICSA-N 0.000 description 1
• MXQPYUGJHDHNBG-DTORHVGOSA-N (3ar,6as)-5-(5-fluoropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound FC1=CN=CC(N2C[C@H]3CNC[C@H]3C2)=C1 MXQPYUGJHDHNBG-DTORHVGOSA-N 0.000 description 1
• FISPSGRYTNKFIR-PHIMTYICSA-N (3ar,6as)-5-(6-methylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound C1=NC(C)=CC=C1N1C[C@H]2CNC[C@H]2C1 FISPSGRYTNKFIR-PHIMTYICSA-N 0.000 description 1
• DEARFOHLLIJAOI-AOOOYVTPSA-N (3ar,6as)-5-[5-(2,2,2-trifluoroethoxy)pyridin-3-yl]-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound FC(F)(F)COC1=CN=CC(N2C[C@H]3CNC[C@H]3C2)=C1 DEARFOHLLIJAOI-AOOOYVTPSA-N 0.000 description 1
• AOBSJQWEYXEPBK-BETUJISGSA-N (3ar,6as)-5-benzyl-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound C([C@H]1CNC[C@H]1C1)N1CC1=CC=CC=C1 AOBSJQWEYXEPBK-BETUJISGSA-N 0.000 description 1
• NGULOZCNWLGSBP-GHMZBOCLSA-N (3ar,7ar)-4-(5,6-dichloropyridin-3-yl)-1,2,3,3a,5,6,7,7a-octahydropyrrolo[3,2-b]pyridine Chemical compound N1=C(Cl)C(Cl)=CC(N2[C@@H]3CCN[C@@H]3CCC2)=C1 NGULOZCNWLGSBP-GHMZBOCLSA-N 0.000 description 1
• RWSWISZCTDWWBO-VXGBXAGGSA-N (3ar,7ar)-4-(5-fluoropyridin-3-yl)-1,2,3,3a,5,6,7,7a-octahydropyrrolo[3,2-b]pyridine Chemical compound FC1=CN=CC(N2[C@@H]3CCN[C@@H]3CCC2)=C1 RWSWISZCTDWWBO-VXGBXAGGSA-N 0.000 description 1
• IIOLSYQMSNRKBK-GHMZBOCLSA-N (3ar,7ar)-4-(6-chloro-5-fluoropyridin-3-yl)-1,2,3,3a,5,6,7,7a-octahydropyrrolo[3,2-b]pyridine Chemical compound N1=C(Cl)C(F)=CC(N2[C@@H]3CCN[C@@H]3CCC2)=C1 IIOLSYQMSNRKBK-GHMZBOCLSA-N 0.000 description 1
• XPLNLPRRNKYWAZ-VXGBXAGGSA-N (3ar,7ar)-4-(6-chloro-5-methylpyridin-3-yl)-1,2,3,3a,5,6,7,7a-octahydropyrrolo[3,2-b]pyridine Chemical compound N1=C(Cl)C(C)=CC(N2[C@@H]3CCN[C@@H]3CCC2)=C1 XPLNLPRRNKYWAZ-VXGBXAGGSA-N 0.000 description 1
• SISOZSQETXBELK-GHMZBOCLSA-N (3ar,7ar)-4-(6-chloropyridin-3-yl)-1,2,3,3a,5,6,7,7a-octahydropyrrolo[3,2-b]pyridine Chemical compound C1=NC(Cl)=CC=C1N1[C@@H]2CCN[C@@H]2CCC1 SISOZSQETXBELK-GHMZBOCLSA-N 0.000 description 1
• GWQBVFJNCPLJTI-CHWSQXEVSA-N (3ar,7ar)-4-(6-methylpyridin-3-yl)-1,2,3,3a,5,6,7,7a-octahydropyrrolo[3,2-b]pyridine Chemical compound C1=NC(C)=CC=C1N1[C@@H]2CCN[C@@H]2CCC1 GWQBVFJNCPLJTI-CHWSQXEVSA-N 0.000 description 1
• MSGSLDBBIVJNAI-VXGBXAGGSA-N (3ar,7ar)-4-pyridin-3-yl-1,2,3,3a,5,6,7,7a-octahydropyrrolo[3,2-b]pyridine Chemical compound C([C@@H]1[C@H]2CCN1)CCN2C1=CC=CN=C1 MSGSLDBBIVJNAI-VXGBXAGGSA-N 0.000 description 1
• MPPOKNKISDHROJ-BXKDBHETSA-N (3ar,8as)-7-(5,6-dichloropyridin-3-yl)-2,3,3a,4,5,6,8,8a-octahydro-1h-pyrrolo[2,3-c]azepine Chemical compound N1=C(Cl)C(Cl)=CC(N2C[C@H]3NCC[C@H]3CCC2)=C1 MPPOKNKISDHROJ-BXKDBHETSA-N 0.000 description 1
• NTMCUPPKVJWWSP-ZWNOBZJWSA-N (3ar,8as)-7-(5-fluoropyridin-3-yl)-2,3,3a,4,5,6,8,8a-octahydro-1h-pyrrolo[2,3-c]azepine Chemical compound FC1=CN=CC(N2C[C@H]3NCC[C@H]3CCC2)=C1 NTMCUPPKVJWWSP-ZWNOBZJWSA-N 0.000 description 1
• PYYGTBIEVCBRAC-BXKDBHETSA-N (3ar,8as)-7-(6-chloro-5-fluoropyridin-3-yl)-2,3,3a,4,5,6,8,8a-octahydro-1h-pyrrolo[2,3-c]azepine Chemical compound N1=C(Cl)C(F)=CC(N2C[C@H]3NCC[C@H]3CCC2)=C1 PYYGTBIEVCBRAC-BXKDBHETSA-N 0.000 description 1
• HHZXLUJZWCPALE-DGCLKSJQSA-N (3ar,8as)-7-(6-chloro-5-methylpyridin-3-yl)-2,3,3a,4,5,6,8,8a-octahydro-1h-pyrrolo[2,3-c]azepine Chemical compound N1=C(Cl)C(C)=CC(N2C[C@H]3NCC[C@H]3CCC2)=C1 HHZXLUJZWCPALE-DGCLKSJQSA-N 0.000 description 1
• UCKZTIZEMVTGGU-ZYHUDNBSSA-N (3ar,8as)-7-(6-chloropyridin-3-yl)-2,3,3a,4,5,6,8,8a-octahydro-1h-pyrrolo[2,3-c]azepine Chemical compound C1=NC(Cl)=CC=C1N1C[C@H]2NCC[C@H]2CCC1 UCKZTIZEMVTGGU-ZYHUDNBSSA-N 0.000 description 1
• FYGMDRKVDIHRGZ-TZMCWYRMSA-N (3ar,8as)-7-(6-methylpyridin-3-yl)-2,3,3a,4,5,6,8,8a-octahydro-1h-pyrrolo[2,3-c]azepine Chemical compound C1=NC(C)=CC=C1N1C[C@H]2NCC[C@H]2CCC1 FYGMDRKVDIHRGZ-TZMCWYRMSA-N 0.000 description 1
• MZYLXNDLYJNWNL-DGCLKSJQSA-N (3ar,8as)-7-pyridin-3-yl-2,3,3a,4,5,6,8,8a-octahydro-1h-pyrrolo[2,3-c]azepine Chemical compound C([C@@H]1CCN[C@@H]1C1)CCN1C1=CC=CN=C1 MZYLXNDLYJNWNL-DGCLKSJQSA-N 0.000 description 1
• SVJQHYYJQQYSHU-BUQWBUBUSA-N (3as,6ar)-5-(5-methoxypyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole;dihydrochloride Chemical compound Cl.Cl.COC1=CN=CC(N2C[C@H]3CNC[C@H]3C2)=C1 SVJQHYYJQQYSHU-BUQWBUBUSA-N 0.000 description 1
• COFHBZBIKPEYNP-PHIMTYICSA-N (3as,6ar)-5-benzyl-3a,4,6,6a-tetrahydropyrrolo[3,4-c]pyrrole-1,3-dione Chemical compound C([C@H]1C(=O)NC([C@H]1C1)=O)N1CC1=CC=CC=C1 COFHBZBIKPEYNP-PHIMTYICSA-N 0.000 description 1
• BYDOZJQQICNGSG-KWCYVHTRSA-N (3as,6as)-1-[(1r)-1-phenylethyl]-3,3a,4,5,6,6a-hexahydro-2h-pyrrolo[3,4-b]pyrrole Chemical compound C1([C@H](N2[C@@H]3CNC[C@@H]3CC2)C)=CC=CC=C1 BYDOZJQQICNGSG-KWCYVHTRSA-N 0.000 description 1
• NCSDFKQTTXROLF-OXFYSEKESA-N (3as,6as)-5-(4-nitrophenyl)sulfonyl-1-[(1r)-1-phenylethyl]-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrole Chemical compound C([C@@H]1CCN([C@@H]1C1)[C@H](C)C=2C=CC=CC=2)N1S(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 NCSDFKQTTXROLF-OXFYSEKESA-N 0.000 description 1
• SKVYNAUBAUHZKE-PKKHVXKMSA-N (3as,6as)-5-(5-methoxypyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.COC1=CN=CC(N2C[C@H]3NCC[C@H]3C2)=C1 SKVYNAUBAUHZKE-PKKHVXKMSA-N 0.000 description 1
• KQCSGXPUXCJWRX-GZMMTYOYSA-N (3as,7ar)-5-(5,6-dichloropyridin-3-yl)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,2-c]pyridine Chemical compound N1=C(Cl)C(Cl)=CC(N2C[C@@H]3CCN[C@@H]3CC2)=C1 KQCSGXPUXCJWRX-GZMMTYOYSA-N 0.000 description 1
• FYKLQIYNGNMSFD-IUCAKERBSA-N (3as,7ar)-5-(5,6-dichloropyridin-3-yl)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,4-c]pyridine Chemical compound N1=C(Cl)C(Cl)=CC(N2C[C@@H]3CNC[C@@H]3CC2)=C1 FYKLQIYNGNMSFD-IUCAKERBSA-N 0.000 description 1
• GSMPEMQHEGWOHE-JOYOIKCWSA-N (3as,7ar)-5-(5-fluoropyridin-3-yl)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,2-c]pyridine Chemical compound FC1=CN=CC(N2C[C@@H]3CCN[C@@H]3CC2)=C1 GSMPEMQHEGWOHE-JOYOIKCWSA-N 0.000 description 1
• DVWMQQLOIAODGU-UWVGGRQHSA-N (3as,7ar)-5-(5-fluoropyridin-3-yl)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,4-c]pyridine Chemical compound FC1=CN=CC(N2C[C@@H]3CNC[C@@H]3CC2)=C1 DVWMQQLOIAODGU-UWVGGRQHSA-N 0.000 description 1
• WSYFMYKZOLWLSD-GZMMTYOYSA-N (3as,7ar)-5-(6-chloro-5-fluoropyridin-3-yl)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,2-c]pyridine Chemical compound N1=C(Cl)C(F)=CC(N2C[C@@H]3CCN[C@@H]3CC2)=C1 WSYFMYKZOLWLSD-GZMMTYOYSA-N 0.000 description 1
• DHYKAKGWYYCJMC-IUCAKERBSA-N (3as,7ar)-5-(6-chloro-5-fluoropyridin-3-yl)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,4-c]pyridine Chemical compound N1=C(Cl)C(F)=CC(N2C[C@@H]3CNC[C@@H]3CC2)=C1 DHYKAKGWYYCJMC-IUCAKERBSA-N 0.000 description 1
• VAVFCDBRWCRUOC-CMPLNLGQSA-N (3as,7ar)-5-(6-chloro-5-methylpyridin-3-yl)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,2-c]pyridine Chemical compound N1=C(Cl)C(C)=CC(N2C[C@@H]3CCN[C@@H]3CC2)=C1 VAVFCDBRWCRUOC-CMPLNLGQSA-N 0.000 description 1
• QYRBHWSSAMDGHP-QWRGUYRKSA-N (3as,7ar)-5-(6-chloro-5-methylpyridin-3-yl)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,4-c]pyridine Chemical compound N1=C(Cl)C(C)=CC(N2C[C@@H]3CNC[C@@H]3CC2)=C1 QYRBHWSSAMDGHP-QWRGUYRKSA-N 0.000 description 1
• DVKQABJHRNBSDE-GXSJLCMTSA-N (3as,7ar)-5-(6-chloropyridin-3-yl)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,2-c]pyridine Chemical compound C1=NC(Cl)=CC=C1N1C[C@@H]2CCN[C@@H]2CC1 DVKQABJHRNBSDE-GXSJLCMTSA-N 0.000 description 1
• ANLNMDONIHDNAT-UWVGGRQHSA-N (3as,7ar)-5-(6-chloropyridin-3-yl)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,4-c]pyridine Chemical compound C1=NC(Cl)=CC=C1N1C[C@@H]2CNC[C@@H]2CC1 ANLNMDONIHDNAT-UWVGGRQHSA-N 0.000 description 1
• LNBVLMANTHIXBV-WCQYABFASA-N (3as,7ar)-5-(6-methylpyridin-3-yl)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,2-c]pyridine Chemical compound C1=NC(C)=CC=C1N1C[C@@H]2CCN[C@@H]2CC1 LNBVLMANTHIXBV-WCQYABFASA-N 0.000 description 1
• MPBWQGNSOFEQIN-RYUDHWBXSA-N (3as,7ar)-5-(6-methylpyridin-3-yl)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,4-c]pyridine Chemical compound C1=NC(C)=CC=C1N1C[C@@H]2CNC[C@@H]2CC1 MPBWQGNSOFEQIN-RYUDHWBXSA-N 0.000 description 1
• SRIQRGIGQGVSLC-CMPLNLGQSA-N (3as,7ar)-5-pyridin-3-yl-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,2-c]pyridine Chemical compound C([C@@H]1CCN[C@@H]1CC1)N1C1=CC=CN=C1 SRIQRGIGQGVSLC-CMPLNLGQSA-N 0.000 description 1
• LVTBJDSIVXNLOV-QWRGUYRKSA-N (3as,7ar)-5-pyridin-3-yl-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,4-c]pyridine Chemical compound C([C@@H]1CNC[C@@H]1CC1)N1C1=CC=CN=C1 LVTBJDSIVXNLOV-QWRGUYRKSA-N 0.000 description 1
• ORYAVRSXZVCUDV-JOYOIKCWSA-N (3as,8ar)-6-(5,6-dichloropyridin-3-yl)-2,3,3a,4,5,7,8,8a-octahydro-1h-pyrrolo[2,3-d]azepine Chemical compound N1=C(Cl)C(Cl)=CC(N2CC[C@H]3NCC[C@H]3CC2)=C1 ORYAVRSXZVCUDV-JOYOIKCWSA-N 0.000 description 1
• UNSSLKPFSTVODC-GXFFZTMASA-N (3as,8ar)-6-(5-fluoropyridin-3-yl)-2,3,3a,4,5,7,8,8a-octahydro-1h-pyrrolo[2,3-d]azepine Chemical compound FC1=CN=CC(N2CC[C@H]3NCC[C@H]3CC2)=C1 UNSSLKPFSTVODC-GXFFZTMASA-N 0.000 description 1
• BZFNONWLZJYWAQ-JOYOIKCWSA-N (3as,8ar)-6-(6-chloro-5-fluoropyridin-3-yl)-2,3,3a,4,5,7,8,8a-octahydro-1h-pyrrolo[2,3-d]azepine Chemical compound N1=C(Cl)C(F)=CC(N2CC[C@H]3NCC[C@H]3CC2)=C1 BZFNONWLZJYWAQ-JOYOIKCWSA-N 0.000 description 1
• UKPNNHOZLBQFDV-WCQYABFASA-N (3as,8ar)-6-(6-chloro-5-methylpyridin-3-yl)-2,3,3a,4,5,7,8,8a-octahydro-1h-pyrrolo[2,3-d]azepine Chemical compound N1=C(Cl)C(C)=CC(N2CC[C@H]3NCC[C@H]3CC2)=C1 UKPNNHOZLBQFDV-WCQYABFASA-N 0.000 description 1
• WWZXCKXCPNFNPS-CMPLNLGQSA-N (3as,8ar)-6-(6-chloropyridin-3-yl)-2,3,3a,4,5,7,8,8a-octahydro-1h-pyrrolo[2,3-d]azepine Chemical compound C1=NC(Cl)=CC=C1N1CC[C@H]2NCC[C@H]2CC1 WWZXCKXCPNFNPS-CMPLNLGQSA-N 0.000 description 1
• ISCKSCKSRNGERF-GXTWGEPZSA-N (3as,8ar)-6-(6-methylpyridin-3-yl)-2,3,3a,4,5,7,8,8a-octahydro-1h-pyrrolo[2,3-d]azepine Chemical compound C1=NC(C)=CC=C1N1CC[C@H]2NCC[C@H]2CC1 ISCKSCKSRNGERF-GXTWGEPZSA-N 0.000 description 1
• DNYVCGHKEGTDNQ-WCQYABFASA-N (3as,8ar)-6-pyridin-3-yl-2,3,3a,4,5,7,8,8a-octahydro-1h-pyrrolo[2,3-d]azepine Chemical compound C([C@@H]1CCN[C@@H]1CC1)CN1C1=CC=CN=C1 DNYVCGHKEGTDNQ-WCQYABFASA-N 0.000 description 1
• GQKOAWHXFKIRMM-WCFLWFBJSA-N (3s,4s)-3-[[(1s)-1-phenylethyl]amino]piperidine-1,4-dicarboxylic acid Chemical compound N([C@@H](C)C=1C=CC=CC=1)[C@@H]1CN(C(O)=O)CC[C@@H]1C(O)=O GQKOAWHXFKIRMM-WCFLWFBJSA-N 0.000 description 1
• LNJNYZUUTWCJRC-KCJUWKMLSA-N (4ar,7ar)-1-(5,6-dichloropyridin-3-yl)-2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine Chemical compound N1=C(Cl)C(Cl)=CC(N2[C@H]3CNC[C@H]3CCC2)=C1 LNJNYZUUTWCJRC-KCJUWKMLSA-N 0.000 description 1
• PYXNQNJNAGBBCK-SKDRFNHKSA-N (4ar,7ar)-1-(5-fluoropyridin-3-yl)-2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine Chemical compound FC1=CN=CC(N2[C@H]3CNC[C@H]3CCC2)=C1 PYXNQNJNAGBBCK-SKDRFNHKSA-N 0.000 description 1
• ZJMVACHVQVNKOA-KCJUWKMLSA-N (4ar,7ar)-1-(6-chloro-5-fluoropyridin-3-yl)-2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine Chemical compound N1=C(Cl)C(F)=CC(N2[C@H]3CNC[C@H]3CCC2)=C1 ZJMVACHVQVNKOA-KCJUWKMLSA-N 0.000 description 1
• VDDGZOKRYUPHEA-PWSUYJOCSA-N (4ar,7ar)-1-(6-chloro-5-methylpyridin-3-yl)-2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine Chemical compound N1=C(Cl)C(C)=CC(N2[C@H]3CNC[C@H]3CCC2)=C1 VDDGZOKRYUPHEA-PWSUYJOCSA-N 0.000 description 1
• XKBATZFRVPAUPF-KOLCDFICSA-N (4ar,7ar)-1-(6-chloropyridin-3-yl)-2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine Chemical compound C1=NC(Cl)=CC=C1N1[C@H]2CNC[C@H]2CCC1 XKBATZFRVPAUPF-KOLCDFICSA-N 0.000 description 1
• XQTPMJANKMYKPS-YPMHNXCESA-N (4ar,7ar)-1-(6-methylpyridin-3-yl)-2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine Chemical compound C1=NC(C)=CC=C1N1[C@H]2CNC[C@H]2CCC1 XQTPMJANKMYKPS-YPMHNXCESA-N 0.000 description 1
• MFHAOMBSDYEWTK-PWSUYJOCSA-N (4ar,7ar)-1-pyridin-3-yl-2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine Chemical compound C([C@H]1[C@@H]2CNC1)CCN2C1=CC=CN=C1 MFHAOMBSDYEWTK-PWSUYJOCSA-N 0.000 description 1
• ZRDHUIBTFTYXSF-PWSUYJOCSA-N (4ar,7ar)-6-pyridin-3-yl-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridine Chemical compound C([C@@H]1NCCC[C@@H]1C1)N1C1=CC=CN=C1 ZRDHUIBTFTYXSF-PWSUYJOCSA-N 0.000 description 1
• IWYDHOAUDWTVEP-SSDOTTSWSA-M (R)-mandelate Chemical compound [O-]C(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-M 0.000 description 1
• IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 description 1
• IWYDHOAUDWTVEP-ZETCQYMHSA-N (S)-mandelic acid Chemical compound OC(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-N 0.000 description 1
• 229930182840 (S)-nicotine Natural products 0.000 description 1
• OCOFKYFBCXTERD-XXKWJKJXSA-N (e)-but-2-enedioic acid;(1s,6r)-7-(6-chloropyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound OC(=O)\C=C\C(O)=O.C1=NC(Cl)=CC=C1N1[C@H]2CNCC[C@H]2C1 OCOFKYFBCXTERD-XXKWJKJXSA-N 0.000 description 1
• PASKJJGPVQGRTN-KCNVDIGLSA-N (e)-but-2-enedioic acid;5-[(1r,6s)-4,7-diazabicyclo[4.2.0]octan-7-yl]pyridine-3-carbonitrile Chemical compound OC(=O)\C=C\C(O)=O.N#CC1=CN=CC(N2[C@@H]3CNCC[C@@H]3C2)=C1 PASKJJGPVQGRTN-KCNVDIGLSA-N 0.000 description 1
• OSANFONRYANBRD-WLHGVMLRSA-N (e)-but-2-enedioic acid;octane Chemical compound CCCCCCCC.OC(=O)\C=C\C(O)=O OSANFONRYANBRD-WLHGVMLRSA-N 0.000 description 1
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
• FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 description 1
• GLUABPSZMHYCNO-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropyrrolo[3,2-b]pyrrole Chemical compound N1CCC2NCCC21 GLUABPSZMHYCNO-UHFFFAOYSA-N 0.000 description 1
• DGDYEWHHLLKNRD-UHFFFAOYSA-N 1,2,3,4-tetrahydroazepin-7-one Chemical compound O=C1NCCCC=C1 DGDYEWHHLLKNRD-UHFFFAOYSA-N 0.000 description 1
• PDGKMPLHZMPYBV-UHFFFAOYSA-N 1,2,3,6a-tetrahydropyrrolo[3,4-c]pyrrole Chemical compound N1=CC2CNCC2=C1 PDGKMPLHZMPYBV-UHFFFAOYSA-N 0.000 description 1
• 125000005871 1,3-benzodioxolyl group Chemical group 0.000 description 1
• BOMUADPKDXMXIH-UHFFFAOYSA-M 1,3-bis(1-methylquinolin-1-ium-6-yl)urea;methyl sulfate Chemical compound COS([O-])(=O)=O.COS([O-])(=O)=O.C[N+]1=CC=CC2=CC(NC(=O)NC=3C=C4C=CC=[N+](C4=CC=3)C)=CC=C21 BOMUADPKDXMXIH-UHFFFAOYSA-M 0.000 description 1
• 229940058015 1,3-butylene glycol Drugs 0.000 description 1
• JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 1
• VSOSXKMEQPYESP-UHFFFAOYSA-N 1,6-naphthyridine Chemical compound C1=CN=CC2=CC=CN=C21 VSOSXKMEQPYESP-UHFFFAOYSA-N 0.000 description 1
• JNEJHGZIUNFUBG-BNOWGMLFSA-N 1-[(3ar,6ar)-1-[(1r)-1-phenylethyl]-2,3,3a,4,6,6a-hexahydropyrrolo[3,4-b]pyrrol-5-yl]-2,2,2-trifluoroethanone Chemical compound C1([C@H](N2[C@H]3CN(C[C@H]3CC2)C(=O)C(F)(F)F)C)=CC=CC=C1 JNEJHGZIUNFUBG-BNOWGMLFSA-N 0.000 description 1
• JNEJHGZIUNFUBG-KWCYVHTRSA-N 1-[(3as,6as)-1-[(1r)-1-phenylethyl]-2,3,3a,4,6,6a-hexahydropyrrolo[3,4-b]pyrrol-5-yl]-2,2,2-trifluoroethanone Chemical compound C1([C@H](N2[C@@H]3CN(C[C@@H]3CC2)C(=O)C(F)(F)F)C)=CC=CC=C1 JNEJHGZIUNFUBG-KWCYVHTRSA-N 0.000 description 1
• 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
• WCTXJAXKORIYNA-UHFFFAOYSA-N 1-o-tert-butyl 4-o-ethyl 3-oxopiperidine-1,4-dicarboxylate Chemical compound CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CC1=O WCTXJAXKORIYNA-UHFFFAOYSA-N 0.000 description 1
• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
• 125000006017 1-propenyl group Chemical group 0.000 description 1
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
• LFDGRWDETVOGDT-UHFFFAOYSA-N 1h-pyrrole;hydrochloride Chemical compound Cl.C=1C=CNC=1 LFDGRWDETVOGDT-UHFFFAOYSA-N 0.000 description 1
• XLKDJOPOOHHZAN-UHFFFAOYSA-N 1h-pyrrolo[2,3-c]pyridine Chemical compound C1=NC=C2NC=CC2=C1 XLKDJOPOOHHZAN-UHFFFAOYSA-N 0.000 description 1
• XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 description 1
• SRSKXJVMVSSSHB-UHFFFAOYSA-N 1h-pyrrolo[3,2-c]pyridine Chemical compound N1=CC=C2NC=CC2=C1 SRSKXJVMVSSSHB-UHFFFAOYSA-N 0.000 description 1
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
• QKWWDTYDYOFRJL-UHFFFAOYSA-N 2,2-dimethoxyethanamine Chemical compound COC(CN)OC QKWWDTYDYOFRJL-UHFFFAOYSA-N 0.000 description 1
• YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
• IJVGODUTGYOVKR-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-pyrrolo[3,2-b]pyridine Chemical compound N1CCCC2NCCC21 IJVGODUTGYOVKR-UHFFFAOYSA-N 0.000 description 1
• JMWPSCUIQIMVQH-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-pyrrolo[3,4-c]pyridine Chemical compound C1NCCC2CNCC21 JMWPSCUIQIMVQH-UHFFFAOYSA-N 0.000 description 1
• 125000003660 2,3-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• SSNMISUJOQAFRR-UHFFFAOYSA-N 2,6-naphthyridine Chemical compound N1=CC=C2C=NC=CC2=C1 SSNMISUJOQAFRR-UHFFFAOYSA-N 0.000 description 1
• HCMMECMKVPHMDE-UHFFFAOYSA-N 2,7-naphthyridine Chemical compound C1=NC=C2C=NC=CC2=C1 HCMMECMKVPHMDE-UHFFFAOYSA-N 0.000 description 1
• BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical group FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
• RFEBVEWGRABHPU-MRVPVSSYSA-N 2-[[(1r)-1-phenylethyl]azaniumyl]acetate Chemical compound OC(=O)CN[C@H](C)C1=CC=CC=C1 RFEBVEWGRABHPU-MRVPVSSYSA-N 0.000 description 1
• 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 description 1
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
• QHLLSQQQAYMXAK-UHFFFAOYSA-N 2-benzyl-3a,4,5,6,7,7a-hexahydropyrrolo[3,4-c]pyridine-1,3-dione Chemical compound O=C1C2CCNCC2C(=O)N1CC1=CC=CC=C1 QHLLSQQQAYMXAK-UHFFFAOYSA-N 0.000 description 1
• IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
• VPJXQGSRWJZDOB-UHFFFAOYSA-O 2-carbamoyloxyethyl(trimethyl)azanium Chemical compound C[N+](C)(C)CCOC(N)=O VPJXQGSRWJZDOB-UHFFFAOYSA-O 0.000 description 1
• 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
• JHARVUVBTAAPLA-UHFFFAOYSA-N 2-chloro-4-methyl-3-nitropyridine Chemical compound CC1=CC=NC(Cl)=C1[N+]([O-])=O JHARVUVBTAAPLA-UHFFFAOYSA-N 0.000 description 1
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
• 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
• 229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
• WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-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
• RPZVZCUMJDFFTE-UHFFFAOYSA-N 3-bromo-5-propoxypyridine Chemical compound CCCOC1=CN=CC(Br)=C1 RPZVZCUMJDFFTE-UHFFFAOYSA-N 0.000 description 1
• ZGIKWINFUGEQEO-UHFFFAOYSA-N 3-bromoquinoline Chemical compound C1=CC=CC2=CC(Br)=CN=C21 ZGIKWINFUGEQEO-UHFFFAOYSA-N 0.000 description 1
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
• 125000003469 3-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 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
• FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• LJCWONGJFPCTTL-UHFFFAOYSA-N 4-hydroxyphenylglycine Chemical compound OC(=O)C(N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-UHFFFAOYSA-N 0.000 description 1
• IBKMZYWDWWIWEL-UHFFFAOYSA-N 4-methylpyridin-3-amine Chemical compound CC1=CC=NC=C1N IBKMZYWDWWIWEL-UHFFFAOYSA-N 0.000 description 1
• JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 description 1
• RLNJDOSAGVFXQU-HOTGVXAUSA-N 4-o-benzyl 7-o-tert-butyl (1s,6r)-4,7-diazabicyclo[4.2.0]octane-4,7-dicarboxylate Chemical compound C([C@H]1CN([C@H]1C1)C(=O)OC(C)(C)C)CN1C(=O)OCC1=CC=CC=C1 RLNJDOSAGVFXQU-HOTGVXAUSA-N 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
• DHAPEAFRILEWCS-JQWIXIFHSA-N 5-[(1s,6r)-4,7-diazabicyclo[4.2.0]octan-4-yl]pyridine-3-carbonitrile Chemical compound N#CC1=CN=CC(N2C[C@@H]3NC[C@@H]3CC2)=C1 DHAPEAFRILEWCS-JQWIXIFHSA-N 0.000 description 1
• MJIVIYRHMBKPHN-QGMICOJFSA-N 5-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]pyridine-3-carbonitrile;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.N#CC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 MJIVIYRHMBKPHN-QGMICOJFSA-N 0.000 description 1
• JJRVGUPFYLTYGR-CMPLNLGQSA-N 5-[(3as,6as)-3,3a,4,5,6,6a-hexahydro-2h-pyrrolo[2,3-c]pyrrol-1-yl]pyridine-3-carbonitrile Chemical compound N#CC1=CN=CC(N2[C@@H]3CNC[C@@H]3CC2)=C1 JJRVGUPFYLTYGR-CMPLNLGQSA-N 0.000 description 1
• LXCSZZBDTLNNQB-JTQLQIEISA-N 5-[[(1S)-1-phenylethyl]amino]-3,6-dihydro-2H-pyridine-1,4-dicarboxylic acid Chemical compound C1(=CC=CC=C1)[C@H](C)NC1=C(CCN(C1)C(=O)O)C(=O)O LXCSZZBDTLNNQB-JTQLQIEISA-N 0.000 description 1
• COFHBZBIKPEYNP-UHFFFAOYSA-N 5-benzyl-3a,4,6,6a-tetrahydropyrrolo[3,4-c]pyrrole-1,3-dione Chemical compound C1C2C(=O)NC(=O)C2CN1CC1=CC=CC=C1 COFHBZBIKPEYNP-UHFFFAOYSA-N 0.000 description 1
• GFJMOZYIDADKLJ-UHFFFAOYSA-N 5-bromo-2-chloro-3-methoxypyridine Chemical compound COC1=CC(Br)=CN=C1Cl GFJMOZYIDADKLJ-UHFFFAOYSA-N 0.000 description 1
• KVDIPLHFSIUSIK-UHFFFAOYSA-N 5-bromo-2-chloropyridin-3-ol Chemical compound OC1=CC(Br)=CN=C1Cl KVDIPLHFSIUSIK-UHFFFAOYSA-N 0.000 description 1
• HXPMRPRBABWPKL-UHFFFAOYSA-N 5-bromo-3-methyl-1h-pyridin-2-one Chemical compound CC1=CC(Br)=CN=C1O HXPMRPRBABWPKL-UHFFFAOYSA-N 0.000 description 1
• KBLGGRWUEVCNPY-UHFFFAOYSA-N 5-bromo-3-methylpyridin-2-amine Chemical compound CC1=CC(Br)=CN=C1N KBLGGRWUEVCNPY-UHFFFAOYSA-N 0.000 description 1
• YOQRXZIMSKLRCY-UHFFFAOYSA-N 5-bromonicotinamide Chemical compound NC(=O)C1=CN=CC(Br)=C1 YOQRXZIMSKLRCY-UHFFFAOYSA-N 0.000 description 1
• VNYBIBSZZDAEOK-UHFFFAOYSA-N 5-bromopyridin-3-ol Chemical compound OC1=CN=CC(Br)=C1 VNYBIBSZZDAEOK-UHFFFAOYSA-N 0.000 description 1
• UUEUWKVPXODVMJ-UHFFFAOYSA-N 5-bromopyridine-3-carbonitrile phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O.BrC1=CN=CC(C#N)=C1 UUEUWKVPXODVMJ-UHFFFAOYSA-N 0.000 description 1
• 125000006043 5-hexenyl group Chemical group 0.000 description 1
• RZYCOPGGQSSESS-UHFFFAOYSA-N 6-(6-chloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound C1=NC(Cl)=CC=C1N1C2CNCC2C1 RZYCOPGGQSSESS-UHFFFAOYSA-N 0.000 description 1
• CWWCTIYOOFSTKG-LDYMZIIASA-N 6-[(1r,5s)-3,6-diazabicyclo[3.2.0]heptan-6-yl]furo[3,2-b]pyridine Chemical compound N1=C2C=COC2=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 CWWCTIYOOFSTKG-LDYMZIIASA-N 0.000 description 1
• NLNLYTQHNWFDNT-BXKDBHETSA-N 6-[(1r,6r)-4,8-diazabicyclo[4.2.0]octan-8-yl]furo[3,2-b]pyridine Chemical compound N1=C2C=COC2=CC(N2[C@@H]3CCNC[C@@H]3C2)=C1 NLNLYTQHNWFDNT-BXKDBHETSA-N 0.000 description 1
• HGPZXIDSRXWOMT-ZYHUDNBSSA-N 6-[(1r,7r)-4,8-diazabicyclo[5.2.0]nonan-4-yl]furo[3,2-b]pyridine Chemical compound C([C@H]1NC[C@H]1CC1)CN1C1=CN=C(C=CO2)C2=C1 HGPZXIDSRXWOMT-ZYHUDNBSSA-N 0.000 description 1
• QHCHOFCMFBHGDP-GZMMTYOYSA-N 6-[(1s,5s)-3,6-diazabicyclo[3.2.0]heptan-3-yl]furo[3,2-b]pyridine Chemical compound N1=C2C=COC2=CC(N2C[C@H]3NC[C@H]3C2)=C1 QHCHOFCMFBHGDP-GZMMTYOYSA-N 0.000 description 1
• DQAHXLSLFYGDDC-CABZTGNLSA-N 6-[(1s,6r)-4,7-diazabicyclo[4.2.0]octan-4-yl]furo[3,2-b]pyridine Chemical compound N1=C2C=COC2=CC(N2C[C@@H]3NC[C@@H]3CC2)=C1 DQAHXLSLFYGDDC-CABZTGNLSA-N 0.000 description 1
• KFLYQBOKLKNANM-CABZTGNLSA-N 6-[(1s,6r)-4,7-diazabicyclo[4.2.0]octan-7-yl]furo[3,2-b]pyridine Chemical compound N1=C2C=COC2=CC(N2[C@H]3CNCC[C@H]3C2)=C1 KFLYQBOKLKNANM-CABZTGNLSA-N 0.000 description 1
• OLLGOIWIWCTIIH-GWCFXTLKSA-N 6-[(1s,7r)-5,8-diazabicyclo[5.2.0]nonan-5-yl]furo[3,2-b]pyridine Chemical compound C1CC[C@H]2CN[C@H]2CN1C1=CN=C(C=CO2)C2=C1 OLLGOIWIWCTIIH-GWCFXTLKSA-N 0.000 description 1
• BYSSTXQZDLJWLA-AOOOYVTPSA-N 6-[(3ar,6as)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrol-5-yl]furo[3,2-b]pyridine Chemical compound N1=C2C=COC2=CC(N2C[C@H]3CNC[C@H]3C2)=C1 BYSSTXQZDLJWLA-AOOOYVTPSA-N 0.000 description 1
• KOILAMPZABYPRC-DGCLKSJQSA-N 6-[(3ar,7ar)-1,2,3,3a,5,6,7,7a-octahydropyrrolo[3,2-b]pyridin-4-yl]furo[3,2-b]pyridine Chemical compound N1=C2C=COC2=CC(N2CCC[C@@H]3[C@H]2CCN3)=C1 KOILAMPZABYPRC-DGCLKSJQSA-N 0.000 description 1
• BSMANOWPIXPXAT-BXUZGUMPSA-N 6-[(3ar,8as)-2,3,3a,4,5,6,8,8a-octahydro-1h-pyrrolo[2,3-c]azepin-7-yl]furo[3,2-b]pyridine Chemical compound C([C@@H]1CCN[C@@H]1C1)CCN1C1=CN=C(C=CO2)C2=C1 BSMANOWPIXPXAT-BXUZGUMPSA-N 0.000 description 1
• LBMIZQSULCGOEA-CMPLNLGQSA-N 6-[(3as,7ar)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,2-c]pyridin-5-yl]furo[3,2-b]pyridine Chemical compound N1=C2C=COC2=CC(N2C[C@@H]3CCN[C@@H]3CC2)=C1 LBMIZQSULCGOEA-CMPLNLGQSA-N 0.000 description 1
• DRIWNKCANPXTHZ-QWRGUYRKSA-N 6-[(3as,7ar)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,4-c]pyridin-5-yl]furo[3,2-b]pyridine Chemical compound N1=C2C=COC2=CC(N2C[C@@H]3CNC[C@@H]3CC2)=C1 DRIWNKCANPXTHZ-QWRGUYRKSA-N 0.000 description 1
• UYOKUTLVJRJYEO-WCQYABFASA-N 6-[(3as,8ar)-2,3,3a,4,5,7,8,8a-octahydro-1h-pyrrolo[2,3-d]azepin-6-yl]furo[3,2-b]pyridine Chemical compound C([C@@H]1CCN[C@@H]1CC1)CN1C1=CN=C(C=CO2)C2=C1 UYOKUTLVJRJYEO-WCQYABFASA-N 0.000 description 1
• AYJVSKJYFCBXHI-MFKMUULPSA-N 6-[(4ar,7ar)-2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridin-1-yl]furo[3,2-b]pyridine Chemical compound N1=C2C=COC2=CC(N2CCC[C@H]3[C@@H]2CNC3)=C1 AYJVSKJYFCBXHI-MFKMUULPSA-N 0.000 description 1
• WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
• XHYQJTGLPJMMEB-UHFFFAOYSA-N 6-pyridin-3-yl-3,6-diazabicyclo[3.2.0]heptane Chemical compound C1C2CNCC2N1C1=CC=CN=C1 XHYQJTGLPJMMEB-UHFFFAOYSA-N 0.000 description 1
• 206010000087 Abdominal pain upper Diseases 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• 208000007848 Alcoholism Diseases 0.000 description 1
• 239000005995 Aluminium silicate Substances 0.000 description 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
• 241000416162 Astragalus gummifer Species 0.000 description 1
• 102000007527 Autoreceptors Human genes 0.000 description 1
• 108010071131 Autoreceptors Proteins 0.000 description 1
• 238000006237 Beckmann rearrangement reaction Methods 0.000 description 1
• FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-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
• JKKQNKLKJZOJBB-UHFFFAOYSA-N C(C)O.BrC=1C=NC=C(C1)OCC Chemical compound C(C)O.BrC=1C=NC=C(C1)OCC JKKQNKLKJZOJBB-UHFFFAOYSA-N 0.000 description 1
• AZQBPXDZPZPTQP-VXGBXAGGSA-N C([C@H]1CCNC[C@H]1CC1)N1C1=CC=CN=C1 Chemical compound C([C@H]1CCNC[C@H]1CC1)N1C1=CC=CN=C1 AZQBPXDZPZPTQP-VXGBXAGGSA-N 0.000 description 1
• YTJLRSUNQSRYPV-PWSUYJOCSA-N C1=NC(C)=CC=C1N1C[C@@H]2NCC[C@@H]2C1 Chemical compound C1=NC(C)=CC=C1N1C[C@@H]2NCC[C@@H]2C1 YTJLRSUNQSRYPV-PWSUYJOCSA-N 0.000 description 1
• TZSDAJRMFREETH-CHWSQXEVSA-N C1=NC(C)=CC=C1N1C[C@H]2CCNC[C@H]2CC1 Chemical compound C1=NC(C)=CC=C1N1C[C@H]2CCNC[C@H]2CC1 TZSDAJRMFREETH-CHWSQXEVSA-N 0.000 description 1
• VEKXUTMWUGWABO-WCQYABFASA-N C1=NC(C)=CC=C1N1C[C@H]2NCC[C@H]2CC1 Chemical compound C1=NC(C)=CC=C1N1C[C@H]2NCC[C@H]2CC1 VEKXUTMWUGWABO-WCQYABFASA-N 0.000 description 1
• RRSWMWSQRRLIIS-PWSUYJOCSA-N C1=NC(C)=CC=C1N1[C@H]2CNC[C@H]2CC1 Chemical compound C1=NC(C)=CC=C1N1[C@H]2CNC[C@H]2CC1 RRSWMWSQRRLIIS-PWSUYJOCSA-N 0.000 description 1
• LOAOMRSCWAUOLL-GHMZBOCLSA-N C1=NC(Cl)=CC=C1N1C[C@H]2CCNC[C@H]2CC1 Chemical compound C1=NC(Cl)=CC=C1N1C[C@H]2CCNC[C@H]2CC1 LOAOMRSCWAUOLL-GHMZBOCLSA-N 0.000 description 1
• BVFIBUJCNCDDNR-GXSJLCMTSA-N C1=NC(Cl)=CC=C1N1C[C@H]2NCC[C@H]2CC1 Chemical compound C1=NC(Cl)=CC=C1N1C[C@H]2NCC[C@H]2CC1 BVFIBUJCNCDDNR-GXSJLCMTSA-N 0.000 description 1
• HZNMTBOKLMJXDI-HUUCEWRRSA-N CC(C)(C)OC(=O)N[C@H]1C[C@H](CN1C(=O)OCC2=CC=CC=C2)CO Chemical compound CC(C)(C)OC(=O)N[C@H]1C[C@H](CN1C(=O)OCC2=CC=CC=C2)CO HZNMTBOKLMJXDI-HUUCEWRRSA-N 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
• 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
• 241001111317 Chondrodendron tomentosum Species 0.000 description 1
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
• KFVKTLUZUGGDKC-FQDOXHKTSA-N Cl.Cl.C1=CC=CC2=CC(N3C[C@H]4CNC[C@H]4C3)=CN=C21 Chemical compound Cl.Cl.C1=CC=CC2=CC(N3C[C@H]4CNC[C@H]4C3)=CN=C21 KFVKTLUZUGGDKC-FQDOXHKTSA-N 0.000 description 1
• 229940126062 Compound A Drugs 0.000 description 1
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
• 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
• 239000008709 Curare Substances 0.000 description 1
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 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
• 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
• QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
• HDWLUGYOLUHEMN-UHFFFAOYSA-N Dinobuton Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)OC(C)C HDWLUGYOLUHEMN-UHFFFAOYSA-N 0.000 description 1
• 206010052804 Drug tolerance Diseases 0.000 description 1
• 102000004190 Enzymes Human genes 0.000 description 1
• 108090000790 Enzymes Proteins 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• YHDUAHJZENXNEP-KCJUWKMLSA-N FC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 Chemical compound FC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 YHDUAHJZENXNEP-KCJUWKMLSA-N 0.000 description 1
• QCSLHKBLBSQXIY-GHMZBOCLSA-N FC1=CN=CC(N2C[C@H]3CCNC[C@H]3CC2)=C1 Chemical compound FC1=CN=CC(N2C[C@H]3CCNC[C@H]3CC2)=C1 QCSLHKBLBSQXIY-GHMZBOCLSA-N 0.000 description 1
• JUXGUNVOLPMFNG-JOYOIKCWSA-N FC1=CN=CC(N2C[C@H]3NCC[C@H]3CC2)=C1 Chemical compound FC1=CN=CC(N2C[C@H]3NCC[C@H]3CC2)=C1 JUXGUNVOLPMFNG-JOYOIKCWSA-N 0.000 description 1
• RINRLWOMLQDAEG-KCJUWKMLSA-N FC1=CN=CC(N2[C@H]3CNC[C@H]3CC2)=C1 Chemical compound FC1=CN=CC(N2[C@H]3CNC[C@H]3CC2)=C1 RINRLWOMLQDAEG-KCJUWKMLSA-N 0.000 description 1
• 239000004606 Fillers/Extenders Substances 0.000 description 1
• 108091006027 G proteins Proteins 0.000 description 1
• 102000030782 GTP binding Human genes 0.000 description 1
• 108091000058 GTP-Binding Proteins 0.000 description 1
• 206010017577 Gait disturbance Diseases 0.000 description 1
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Polymers OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
• 239000007818 Grignard reagent Substances 0.000 description 1
• 238000007341 Heck reaction Methods 0.000 description 1
• NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
• SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 1
• 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
• 206010021113 Hypothermia Diseases 0.000 description 1
• 102000004310 Ion Channels Human genes 0.000 description 1
• 108090000862 Ion Channels Proteins 0.000 description 1
• 239000003810 Jones reagent Substances 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
• 206010023644 Lacrimation increased Diseases 0.000 description 1
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
• 240000007472 Leucaena leucocephala Species 0.000 description 1
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
• 229910010082 LiAlH Inorganic materials 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 240000003183 Manihot esculenta Species 0.000 description 1
• 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
• 206010027646 Miosis Diseases 0.000 description 1
• 241000699670 Mus sp. Species 0.000 description 1
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
• BFDWWMRWLXGJNX-UHFFFAOYSA-N N-[(4-ethylphenyl)diazenyl]-N-methylacetamide Chemical compound CCC1=CC=C(N=NN(C)C(C)=O)C=C1 BFDWWMRWLXGJNX-UHFFFAOYSA-N 0.000 description 1
• VKHOXRYUAOQHRN-VXGBXAGGSA-N N1=C(Cl)C(C)=CC(N2C[C@H]3CCNC[C@H]3CC2)=C1 Chemical compound N1=C(Cl)C(C)=CC(N2C[C@H]3CCNC[C@H]3CC2)=C1 VKHOXRYUAOQHRN-VXGBXAGGSA-N 0.000 description 1
• FULBMGFQPTYUEV-CMPLNLGQSA-N N1=C(Cl)C(C)=CC(N2C[C@H]3NCC[C@H]3CC2)=C1 Chemical compound N1=C(Cl)C(C)=CC(N2C[C@H]3NCC[C@H]3CC2)=C1 FULBMGFQPTYUEV-CMPLNLGQSA-N 0.000 description 1
• LTNVMIPLNNLUDU-KOLCDFICSA-N N1=C(Cl)C(C)=CC(N2[C@H]3CNC[C@H]3CC2)=C1 Chemical compound N1=C(Cl)C(C)=CC(N2[C@H]3CNC[C@H]3CC2)=C1 LTNVMIPLNNLUDU-KOLCDFICSA-N 0.000 description 1
• PGJRAHMSGFOGOZ-NXEZZACHSA-N N1=C(Cl)C(Cl)=CC(N2C[C@H]3CCNC[C@H]3CC2)=C1 Chemical compound N1=C(Cl)C(Cl)=CC(N2C[C@H]3CCNC[C@H]3CC2)=C1 PGJRAHMSGFOGOZ-NXEZZACHSA-N 0.000 description 1
• MAHWNRWRZPGLNW-GZMMTYOYSA-N N1=C(Cl)C(Cl)=CC(N2C[C@H]3NCC[C@H]3CC2)=C1 Chemical compound N1=C(Cl)C(Cl)=CC(N2C[C@H]3NCC[C@H]3CC2)=C1 MAHWNRWRZPGLNW-GZMMTYOYSA-N 0.000 description 1
• UQJAMRMJVZFBQB-XCBNKYQSSA-N N1=C(Cl)C(Cl)=CC(N2[C@H]3CNC[C@H]3CC2)=C1 Chemical compound N1=C(Cl)C(Cl)=CC(N2[C@H]3CNC[C@H]3CC2)=C1 UQJAMRMJVZFBQB-XCBNKYQSSA-N 0.000 description 1
• TVLILICOWPMJEF-XCBNKYQSSA-N N1=C(Cl)C(F)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 Chemical compound N1=C(Cl)C(F)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 TVLILICOWPMJEF-XCBNKYQSSA-N 0.000 description 1
• ACIIZSOLSIYIOG-NXEZZACHSA-N N1=C(Cl)C(F)=CC(N2C[C@H]3CCNC[C@H]3CC2)=C1 Chemical compound N1=C(Cl)C(F)=CC(N2C[C@H]3CCNC[C@H]3CC2)=C1 ACIIZSOLSIYIOG-NXEZZACHSA-N 0.000 description 1
• WFTAKVMVZVYDAD-GZMMTYOYSA-N N1=C(Cl)C(F)=CC(N2C[C@H]3NCC[C@H]3CC2)=C1 Chemical compound N1=C(Cl)C(F)=CC(N2C[C@H]3NCC[C@H]3CC2)=C1 WFTAKVMVZVYDAD-GZMMTYOYSA-N 0.000 description 1
• MBGYBSKNPANADU-XCBNKYQSSA-N N1=C(Cl)C(F)=CC(N2[C@H]3CNC[C@H]3CC2)=C1 Chemical compound N1=C(Cl)C(F)=CC(N2[C@H]3CNC[C@H]3CC2)=C1 MBGYBSKNPANADU-XCBNKYQSSA-N 0.000 description 1
• HJBBFCSTHHWMFX-GXFFZTMASA-N N1=C2C=COC2=CC(N2CC[C@@H]3CCN[C@@H]3C2)=C1 Chemical compound N1=C2C=COC2=CC(N2CC[C@@H]3CCN[C@@H]3C2)=C1 HJBBFCSTHHWMFX-GXFFZTMASA-N 0.000 description 1
• ISRQHWYJTYHUQL-SKDRFNHKSA-N N1=C2C=COC2=CC(N2CC[C@@H]3CNC[C@@H]32)=C1 Chemical compound N1=C2C=COC2=CC(N2CC[C@@H]3CNC[C@@H]32)=C1 ISRQHWYJTYHUQL-SKDRFNHKSA-N 0.000 description 1
• HAGZJNYYOZUCMQ-VXGBXAGGSA-N N1=C2C=COC2=CC(N2C[C@H]3CCNC[C@H]3CC2)=C1 Chemical compound N1=C2C=COC2=CC(N2C[C@H]3CCNC[C@H]3CC2)=C1 HAGZJNYYOZUCMQ-VXGBXAGGSA-N 0.000 description 1
• XMCQGQXUXGKGRF-SKDRFNHKSA-N N1=C2C=COC2=CC(N2C[C@H]3CCN[C@H]3C2)=C1 Chemical compound N1=C2C=COC2=CC(N2C[C@H]3CCN[C@H]3C2)=C1 XMCQGQXUXGKGRF-SKDRFNHKSA-N 0.000 description 1
• 229910020889 NaBH3 Inorganic materials 0.000 description 1
• 229910019093 NaOCl Inorganic materials 0.000 description 1
• 238000006411 Negishi coupling reaction Methods 0.000 description 1
• 208000028389 Nerve injury Diseases 0.000 description 1
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
• 102000003840 Opioid Receptors Human genes 0.000 description 1
• 108090000137 Opioid Receptors Proteins 0.000 description 1
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
• CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
• 208000027089 Parkinsonian disease Diseases 0.000 description 1
• 206010034010 Parkinsonism Diseases 0.000 description 1
• 229910002666 PdCl2 Inorganic materials 0.000 description 1
• 235000019483 Peanut oil Nutrition 0.000 description 1
• 229920002230 Pectic acid Polymers 0.000 description 1
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
• 229920002732 Polyanhydride Polymers 0.000 description 1
• 239000004698 Polyethylene Substances 0.000 description 1
• 229920002873 Polyethylenimine Polymers 0.000 description 1
• 229920000954 Polyglycolide Polymers 0.000 description 1
• 229920001710 Polyorthoester Polymers 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
• 239000007868 Raney catalyst Substances 0.000 description 1
• 229910000564 Raney nickel Inorganic materials 0.000 description 1
• 208000034189 Sclerosis Diseases 0.000 description 1
• 206010070834 Sensitisation Diseases 0.000 description 1
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
• DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
• 244000061456 Solanum tuberosum Species 0.000 description 1
• 235000002595 Solanum tuberosum Nutrition 0.000 description 1
• 208000007107 Stomach Ulcer Diseases 0.000 description 1
• 229930006000 Sucrose Natural products 0.000 description 1
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
• 238000006069 Suzuki reaction reaction Methods 0.000 description 1
• 208000001871 Tachycardia Diseases 0.000 description 1
• ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• 206010044565 Tremor Diseases 0.000 description 1
• 208000025865 Ulcer Diseases 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
• 239000002250 absorbent Substances 0.000 description 1
• 230000002745 absorbent Effects 0.000 description 1
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
• 239000012346 acetyl chloride Substances 0.000 description 1
• 238000010306 acid treatment Methods 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
• 239000004480 active ingredient Substances 0.000 description 1
• YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
• WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
• 239000000783 alginic acid Substances 0.000 description 1
• 229960001126 alginic acid Drugs 0.000 description 1
• 150000004781 alginic acids Chemical class 0.000 description 1
• 229910052783 alkali metal Inorganic materials 0.000 description 1
• 150000001340 alkali metals Chemical class 0.000 description 1
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
• 239000002168 alkylating agent Substances 0.000 description 1
• 229940100198 alkylating agent Drugs 0.000 description 1
• BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 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
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-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
• AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 235000012211 aluminium silicate Nutrition 0.000 description 1
• 239000000908 ammonium hydroxide Substances 0.000 description 1
• 230000036592 analgesia Effects 0.000 description 1
• 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
• 239000003242 anti bacterial agent Substances 0.000 description 1
• 230000000844 anti-bacterial effect Effects 0.000 description 1
• 230000001430 anti-depressive effect Effects 0.000 description 1
• 239000003429 antifungal agent Substances 0.000 description 1
• 229940121375 antifungal agent Drugs 0.000 description 1
• 239000008365 aqueous carrier Substances 0.000 description 1
• 239000012736 aqueous medium Substances 0.000 description 1
• 229940009098 aspartate Drugs 0.000 description 1
• 230000002567 autonomic effect Effects 0.000 description 1
• 210000003050 axon Anatomy 0.000 description 1
• 125000002785 azepinyl group Chemical group 0.000 description 1
• 125000002393 azetidinyl group Chemical group 0.000 description 1
• 125000004069 aziridinyl group Chemical group 0.000 description 1
• 125000003828 azulenyl group Chemical group 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
• CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 229940050390 benzoate Drugs 0.000 description 1
• 125000000928 benzodioxinyl group Chemical group O1C(=COC2=C1C=CC=C2)* 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
• 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 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
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
• NDTSRXAMMQDVSW-UHFFFAOYSA-N benzthiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1N=C2CSCC1=CC=CC=C1 NDTSRXAMMQDVSW-UHFFFAOYSA-N 0.000 description 1
• BCONCMOUSFKNCK-NEPJUHHUSA-N benzyl (1r,5r)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate Chemical compound C([C@@H]1NC[C@@H]1C1)N1C(=O)OCC1=CC=CC=C1 BCONCMOUSFKNCK-NEPJUHHUSA-N 0.000 description 1
• ZLTOMYVCMSDSRD-HOCLYGCPSA-N benzyl (1r,5r)-6-(6-chloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate Chemical compound C1=NC(Cl)=CC=C1N1[C@H]2CN(C(=O)OCC=3C=CC=CC=3)C[C@H]2C1 ZLTOMYVCMSDSRD-HOCLYGCPSA-N 0.000 description 1
• JUZMKGYDAATEET-RDJZCZTQSA-N benzyl (1r,5r)-6-pyridin-3-yl-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate Chemical compound C([C@@H]1N(C[C@@H]1C1)C=2C=NC=CC=2)N1C(=O)OCC1=CC=CC=C1 JUZMKGYDAATEET-RDJZCZTQSA-N 0.000 description 1
• BCONCMOUSFKNCK-NWDGAFQWSA-N benzyl (1s,5s)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate Chemical compound C([C@H]1NC[C@H]1C1)N1C(=O)OCC1=CC=CC=C1 BCONCMOUSFKNCK-NWDGAFQWSA-N 0.000 description 1
• RUJMOMNAFIWOQR-RHSMWYFYSA-N benzyl (1s,5s)-6-(5-bromopyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate Chemical compound BrC1=CN=CC(N2[C@@H]3CN(C[C@@H]3C2)C(=O)OCC=2C=CC=CC=2)=C1 RUJMOMNAFIWOQR-RHSMWYFYSA-N 0.000 description 1
• SIMMBCGJYDFCPB-WMZOPIPTSA-N benzyl (1s,6r)-7-(2-nitrophenyl)sulfonyl-4,7-diazabicyclo[4.2.0]octane-4-carboxylate Chemical compound [O-][N+](=O)C1=CC=CC=C1S(=O)(=O)N1[C@H]2CN(C(=O)OCC=3C=CC=CC=3)CC[C@H]2C1 SIMMBCGJYDFCPB-WMZOPIPTSA-N 0.000 description 1
• UVYCLXXPQAPHKR-GJZGRUSLSA-N benzyl (3r,4r)-3-(hydroxymethyl)-4-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidine-1-carboxylate Chemical compound C1[C@@H](CO)[C@@H](NC(=O)OC(C)(C)C)CN1C(=O)OCC1=CC=CC=C1 UVYCLXXPQAPHKR-GJZGRUSLSA-N 0.000 description 1
• UVYCLXXPQAPHKR-HUUCEWRRSA-N benzyl (3s,4s)-3-(hydroxymethyl)-4-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidine-1-carboxylate Chemical compound C1[C@H](CO)[C@H](NC(=O)OC(C)(C)C)CN1C(=O)OCC1=CC=CC=C1 UVYCLXXPQAPHKR-HUUCEWRRSA-N 0.000 description 1
• FQFDLNYJBIFCOO-HZPDHXFCSA-N benzyl (3s,4s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-(methylsulfonyloxymethyl)pyrrolidine-1-carboxylate Chemical compound C1[C@H](COS(C)(=O)=O)[C@H](NC(=O)OC(C)(C)C)CN1C(=O)OCC1=CC=CC=C1 FQFDLNYJBIFCOO-HZPDHXFCSA-N 0.000 description 1
• YXCPNFNWSNFFFZ-VXGBXAGGSA-N benzyl (3s,4s)-3-amino-4-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound C1[C@H](CO)[C@H](N)CN1C(=O)OCC1=CC=CC=C1 YXCPNFNWSNFFFZ-VXGBXAGGSA-N 0.000 description 1
• DGXDJFOLOURKNO-CHWSQXEVSA-N benzyl (3s,4s)-3-amino-4-(methylsulfonyloxymethyl)pyrrolidine-1-carboxylate Chemical compound C1[C@@H](N)[C@@H](COS(=O)(=O)C)CN1C(=O)OCC1=CC=CC=C1 DGXDJFOLOURKNO-CHWSQXEVSA-N 0.000 description 1
• ABCSSQLKCLZNHO-UHFFFAOYSA-N benzyl carbonochloridate;benzyl n-(2,2-dimethoxyethyl)carbamate Chemical compound ClC(=O)OCC1=CC=CC=C1.COC(OC)CNC(=O)OCC1=CC=CC=C1 ABCSSQLKCLZNHO-UHFFFAOYSA-N 0.000 description 1
• JEGCOCKTVYVGSS-UHFFFAOYSA-N benzyl n-(2,2-dimethoxyethyl)-n-prop-2-enylcarbamate Chemical compound COC(OC)CN(CC=C)C(=O)OCC1=CC=CC=C1 JEGCOCKTVYVGSS-UHFFFAOYSA-N 0.000 description 1
• XUEMBLJTQGDMMM-UHFFFAOYSA-N benzyl n-(2-oxoethyl)-n-prop-2-enylcarbamate Chemical compound C=CCN(CC=O)C(=O)OCC1=CC=CC=C1 XUEMBLJTQGDMMM-UHFFFAOYSA-N 0.000 description 1
• USNPGPXWVWTJSS-RIYZIHGNSA-N benzyl n-[(2e)-2-hydroxyiminoethyl]-n-prop-2-enylcarbamate Chemical compound O\N=C\CN(CC=C)C(=O)OCC1=CC=CC=C1 USNPGPXWVWTJSS-RIYZIHGNSA-N 0.000 description 1
• HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 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
• 230000000903 blocking effect Effects 0.000 description 1
• 239000008280 blood Substances 0.000 description 1
• 210000004369 blood Anatomy 0.000 description 1
• 230000036760 body temperature Effects 0.000 description 1
• MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
• 244000309464 bull Species 0.000 description 1
• 235000019437 butane-1,3-diol Nutrition 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
• 239000011575 calcium Substances 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• 229910000019 calcium carbonate Inorganic materials 0.000 description 1
• 235000010216 calcium carbonate Nutrition 0.000 description 1
• 239000001110 calcium chloride Substances 0.000 description 1
• 229910001628 calcium chloride Inorganic materials 0.000 description 1
• 239000001506 calcium phosphate Substances 0.000 description 1
• CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
• 239000008116 calcium stearate Substances 0.000 description 1
• 235000013539 calcium stearate Nutrition 0.000 description 1
• MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical class C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
• 229960004484 carbachol Drugs 0.000 description 1
• 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
• 125000004623 carbolinyl group Chemical group 0.000 description 1
• 150000001721 carbon Chemical group 0.000 description 1
• 239000001768 carboxy methyl cellulose Substances 0.000 description 1
• 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
• 150000001735 carboxylic acids Chemical class 0.000 description 1
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
• 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
• 239000000969 carrier Substances 0.000 description 1
• 239000004359 castor oil Substances 0.000 description 1
• 235000019438 castor oil Nutrition 0.000 description 1
• 150000001768 cations Chemical class 0.000 description 1
• 208000015114 central nervous system disease Diseases 0.000 description 1
• 238000005119 centrifugation Methods 0.000 description 1
• 229960000541 cetyl alcohol Drugs 0.000 description 1
• 229960004926 chlorobutanol Drugs 0.000 description 1
• QOPVNWQGBQYBBP-UHFFFAOYSA-N chloroethyl chloroformate Chemical compound CC(Cl)OC(Cl)=O QOPVNWQGBQYBBP-UHFFFAOYSA-N 0.000 description 1
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
• 239000000064 cholinergic agonist Substances 0.000 description 1
• 238000013375 chromatographic separation Methods 0.000 description 1
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
• 229940001468 citrate Drugs 0.000 description 1
• 239000004927 clay Substances 0.000 description 1
• 239000011248 coating agent Substances 0.000 description 1
• 229940110456 cocoa butter Drugs 0.000 description 1
• 235000019868 cocoa butter Nutrition 0.000 description 1
• 238000004440 column chromatography Methods 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
• 235000005687 corn oil Nutrition 0.000 description 1
• 239000002285 corn oil Substances 0.000 description 1
• 235000012343 cottonseed oil Nutrition 0.000 description 1
• 239000002385 cottonseed oil Substances 0.000 description 1
• 229940111134 coxibs Drugs 0.000 description 1
• 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 1
• 229940027564 cytisine Drugs 0.000 description 1
• 230000001086 cytosolic effect Effects 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
• 230000013872 defecation Effects 0.000 description 1
• 230000007812 deficiency Effects 0.000 description 1
• 230000001934 delay Effects 0.000 description 1
• 230000001419 dependent effect Effects 0.000 description 1
• 230000000994 depressogenic effect Effects 0.000 description 1
• 238000013461 design Methods 0.000 description 1
• 150000008050 dialkyl sulfates Chemical class 0.000 description 1
• 150000004985 diamines Chemical class 0.000 description 1
• 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 description 1
• 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
• WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
• NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
• 229940038472 dicalcium phosphate Drugs 0.000 description 1
• 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
• KJOZJSGOIJQCGA-UHFFFAOYSA-N dichloromethane;2,2,2-trifluoroacetic acid Chemical compound ClCCl.OC(=O)C(F)(F)F KJOZJSGOIJQCGA-UHFFFAOYSA-N 0.000 description 1
• 235000005911 diet Nutrition 0.000 description 1
• 230000037213 diet Effects 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
• 239000003085 diluting agent Substances 0.000 description 1
• 238000010790 dilution Methods 0.000 description 1
• 239000012895 dilution Substances 0.000 description 1
• 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
• VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
• 125000000532 dioxanyl group Chemical group 0.000 description 1
• SXZIXHOMFPUIRK-UHFFFAOYSA-N diphenylmethanimine Chemical compound C=1C=CC=CC=1C(=N)C1=CC=CC=C1 SXZIXHOMFPUIRK-UHFFFAOYSA-N 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 238000004821 distillation Methods 0.000 description 1
• 239000012153 distilled water Substances 0.000 description 1
• 125000005883 dithianyl group Chemical group 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
• 231100000673 dose–response relationship Toxicity 0.000 description 1
• 239000008298 dragée Substances 0.000 description 1
• 239000006196 drop Substances 0.000 description 1
• 238000009510 drug design Methods 0.000 description 1
• 210000001198 duodenum Anatomy 0.000 description 1
• 230000004064 dysfunction Effects 0.000 description 1
• 239000012039 electrophile Substances 0.000 description 1
• 230000008030 elimination Effects 0.000 description 1
• 238000003379 elimination reaction Methods 0.000 description 1
• 230000001804 emulsifying effect Effects 0.000 description 1
• 238000003821 enantio-separation Methods 0.000 description 1
• 238000005516 engineering process Methods 0.000 description 1
• 239000003623 enhancer Substances 0.000 description 1
• 239000002702 enteric coating Substances 0.000 description 1
• 238000009505 enteric coating Methods 0.000 description 1
• BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
• UQOMEAWPKSISII-UHFFFAOYSA-N ethyl 1-benzyl-3-oxopiperidine-4-carboxylate;hydron;chloride Chemical compound Cl.C1C(=O)C(C(=O)OCC)CCN1CC1=CC=CC=C1 UQOMEAWPKSISII-UHFFFAOYSA-N 0.000 description 1
• PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
• IQQODTFRDRREIO-UHFFFAOYSA-N ethyl n-(2-oxoethyl)-n-prop-2-enylcarbamate Chemical compound CCOC(=O)N(CC=C)CC=O IQQODTFRDRREIO-UHFFFAOYSA-N 0.000 description 1
• 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 230000005284 excitation Effects 0.000 description 1
• 230000002964 excitative effect Effects 0.000 description 1
• 230000029142 excretion Effects 0.000 description 1
• 238000002474 experimental method Methods 0.000 description 1
• 239000003885 eye ointment Substances 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 238000003818 flash chromatography Methods 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 235000003599 food sweetener Nutrition 0.000 description 1
• 210000002683 foot Anatomy 0.000 description 1
• FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 description 1
• 239000003205 fragrance Substances 0.000 description 1
• 230000006870 function Effects 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 201000005917 gastric ulcer Diseases 0.000 description 1
• 210000001035 gastrointestinal tract Anatomy 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• 210000004907 gland Anatomy 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• 235000001727 glucose Nutrition 0.000 description 1
• 229930195712 glutamate Natural products 0.000 description 1
• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
• 229940075507 glyceryl monostearate Drugs 0.000 description 1
• 150000002334 glycols Chemical class 0.000 description 1
• 150000004795 grignard reagents Chemical class 0.000 description 1
• 230000026781 habituation Effects 0.000 description 1
• 150000004820 halides Chemical class 0.000 description 1
• 125000005843 halogen group Chemical group 0.000 description 1
• 230000036541 health Effects 0.000 description 1
• 230000003862 health status Effects 0.000 description 1
• MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
• FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
• 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
• 210000000548 hind-foot Anatomy 0.000 description 1
• 150000004677 hydrates Chemical class 0.000 description 1
• 150000007857 hydrazones Chemical class 0.000 description 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
• ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
• 230000002102 hyperpolarization Effects 0.000 description 1
• 230000002631 hypothermal effect Effects 0.000 description 1
• 239000005457 ice water Substances 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
• 150000002466 imines Chemical class 0.000 description 1
• 230000006872 improvement Effects 0.000 description 1
• 238000010348 incorporation Methods 0.000 description 1
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 208000027866 inflammatory disease Diseases 0.000 description 1
• 238000001802 infusion Methods 0.000 description 1
• 239000003112 inhibitor Substances 0.000 description 1
• 230000036734 inhibitory postsynaptic potential Effects 0.000 description 1
• 239000007972 injectable composition Substances 0.000 description 1
• 208000014674 injury Diseases 0.000 description 1
• 229960000367 inositol Drugs 0.000 description 1
• 230000003834 intracellular effect Effects 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 239000007927 intramuscular injection Substances 0.000 description 1
• 238000010255 intramuscular injection Methods 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound 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
• 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 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
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• 239000007951 isotonicity adjuster Substances 0.000 description 1
• 125000003965 isoxazolidinyl group Chemical group 0.000 description 1
• 125000003971 isoxazolinyl group Chemical group 0.000 description 1
• 125000000842 isoxazolyl group Chemical group 0.000 description 1
• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
• 150000002576 ketones Chemical class 0.000 description 1
• 230000004317 lacrimation Effects 0.000 description 1
• 229940067606 lecithin Drugs 0.000 description 1
• 239000004973 liquid crystal related substance Substances 0.000 description 1
• 239000008297 liquid dosage form Substances 0.000 description 1
• 239000012669 liquid formulation Substances 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
• 229910001629 magnesium chloride Inorganic materials 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• 208000024714 major depressive disease Diseases 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 238000001819 mass spectrum Methods 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 230000010534 mechanism of action Effects 0.000 description 1
• 239000002609 medium Substances 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• 230000003340 mental effect Effects 0.000 description 1
• 210000001259 mesencephalon Anatomy 0.000 description 1
• 229910052751 metal Inorganic materials 0.000 description 1
• 239000002184 metal Substances 0.000 description 1
• 238000001465 metallisation Methods 0.000 description 1
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
• 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
• 239000004530 micro-emulsion Substances 0.000 description 1
• 244000005700 microbiome Species 0.000 description 1
• 239000003094 microcapsule Substances 0.000 description 1
• 229940016286 microcrystalline cellulose Drugs 0.000 description 1
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
• 239000008108 microcrystalline cellulose Substances 0.000 description 1
• 230000005012 migration Effects 0.000 description 1
• 238000013508 migration Methods 0.000 description 1
• 230000003547 miosis Effects 0.000 description 1
• 239000011259 mixed solution Substances 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 239000002808 molecular sieve Substances 0.000 description 1
• 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
• CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
• 125000002757 morpholinyl group Chemical group 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
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 description 1
• 125000003136 n-heptyl 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])* 0.000 description 1
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
• 239000007922 nasal spray Substances 0.000 description 1
• 229940097496 nasal spray Drugs 0.000 description 1
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 230000008764 nerve damage Effects 0.000 description 1
• 210000000653 nervous system Anatomy 0.000 description 1
• 239000000842 neuromuscular blocking agent Substances 0.000 description 1
• 235000001968 nicotinic acid Nutrition 0.000 description 1
• 239000011664 nicotinic acid Substances 0.000 description 1
• 231100000344 non-irritating Toxicity 0.000 description 1
• FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 1
• 230000009871 nonspecific binding Effects 0.000 description 1
• OIPZNTLJVJGRCI-UHFFFAOYSA-M octadecanoyloxyaluminum;dihydrate Chemical compound O.O.CCCCCCCCCCCCCCCCCC(=O)O[Al] OIPZNTLJVJGRCI-UHFFFAOYSA-M 0.000 description 1
• 239000003605 opacifier Substances 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 239000000668 oral spray Substances 0.000 description 1
• 229940041678 oral spray Drugs 0.000 description 1
• 150000002895 organic esters Chemical class 0.000 description 1
• 125000005963 oxadiazolidinyl group Chemical group 0.000 description 1
• 125000005882 oxadiazolinyl group Chemical group 0.000 description 1
• 125000001715 oxadiazolyl group Chemical group 0.000 description 1
• 125000000160 oxazolidinyl group Chemical group 0.000 description 1
• 125000005968 oxazolinyl group Chemical group 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 150000002923 oximes Chemical class 0.000 description 1
• 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
• 230000008050 pain signaling Effects 0.000 description 1
• PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
• 239000012188 paraffin wax Substances 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 239000002245 particle Substances 0.000 description 1
• 230000037361 pathway Effects 0.000 description 1
• 239000000312 peanut oil Substances 0.000 description 1
• 239000008188 pellet Substances 0.000 description 1
• 230000035515 penetration Effects 0.000 description 1
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
• 230000002093 peripheral effect Effects 0.000 description 1
• 210000001428 peripheral nervous system Anatomy 0.000 description 1
• 230000035699 permeability Effects 0.000 description 1
• JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
• 239000000825 pharmaceutical preparation Substances 0.000 description 1
• 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
• 229960003742 phenol Drugs 0.000 description 1
• 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
• 125000005954 phenoxathiinyl group Chemical group 0.000 description 1
• 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
• WQMOWDRIXRBJBW-UHFFFAOYSA-N phenyl(piperidin-1-yl)diazene Chemical compound C1CCCCN1N=NC1=CC=CC=C1 WQMOWDRIXRBJBW-UHFFFAOYSA-N 0.000 description 1
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• 150000008105 phosphatidylcholines Chemical class 0.000 description 1
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 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
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 125000003386 piperidinyl group Chemical group 0.000 description 1
• 229950010765 pivalate Drugs 0.000 description 1
• 229920000573 polyethylene Polymers 0.000 description 1
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 238000001556 precipitation Methods 0.000 description 1
• 230000002335 preservative effect Effects 0.000 description 1
• 230000002265 prevention Effects 0.000 description 1
• 150000003141 primary amines Chemical class 0.000 description 1
• 230000002035 prolonged effect Effects 0.000 description 1
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
• UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
• 239000003380 propellant Substances 0.000 description 1
• 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 150000003180 prostaglandins Chemical class 0.000 description 1
• 125000006239 protecting group Chemical group 0.000 description 1
• 102000004169 proteins and genes Human genes 0.000 description 1
• 108090000623 proteins and genes Proteins 0.000 description 1
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
• 125000002755 pyrazolinyl group Chemical group 0.000 description 1
• 125000003226 pyrazolyl group Chemical group 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• 125000004076 pyridyl group Chemical group 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
• SJSABZBUTDSWMJ-UHFFFAOYSA-N pyrrolo[3,4-c]pyridine-1,3-dione Chemical compound N1=CC=C2C(=O)NC(=O)C2=C1 SJSABZBUTDSWMJ-UHFFFAOYSA-N 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
• 230000005855 radiation Effects 0.000 description 1
• 239000002994 raw material Substances 0.000 description 1
• 239000000018 receptor agonist Substances 0.000 description 1
• 229940044601 receptor agonist Drugs 0.000 description 1
• 210000000664 rectum Anatomy 0.000 description 1
• 238000006798 ring closing metathesis reaction Methods 0.000 description 1
• 150000003333 secondary alcohols Chemical class 0.000 description 1
• 150000003335 secondary amines Chemical class 0.000 description 1
• 230000003248 secreting effect Effects 0.000 description 1
• 230000028327 secretion Effects 0.000 description 1
• 230000008313 sensitization Effects 0.000 description 1
• 238000013207 serial dilution Methods 0.000 description 1
• 239000008159 sesame oil Substances 0.000 description 1
• 235000011803 sesame oil Nutrition 0.000 description 1
• 150000004760 silicates Chemical class 0.000 description 1
• RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
• 235000012239 silicon dioxide Nutrition 0.000 description 1
• 230000000391 smoking effect Effects 0.000 description 1
• 210000000329 smooth muscle myocyte Anatomy 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
• 235000017281 sodium acetate Nutrition 0.000 description 1
• 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
• WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
• 239000001509 sodium citrate Substances 0.000 description 1
• NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
• SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
• 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
• 235000010288 sodium nitrite Nutrition 0.000 description 1
• 239000012453 solvate Substances 0.000 description 1
• 230000000392 somatic effect Effects 0.000 description 1
• 239000004334 sorbic acid Substances 0.000 description 1
• 235000010199 sorbic acid Nutrition 0.000 description 1
• 229940075582 sorbic acid Drugs 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 241000894007 species Species 0.000 description 1
• 210000000278 spinal cord Anatomy 0.000 description 1
• 238000013222 sprague-dawley male rat Methods 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 230000006641 stabilisation Effects 0.000 description 1
• 238000011105 stabilization Methods 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000008223 sterile water Substances 0.000 description 1
• 239000003206 sterilizing agent Substances 0.000 description 1
• 210000002784 stomach Anatomy 0.000 description 1
• 238000003860 storage Methods 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 239000007929 subcutaneous injection Substances 0.000 description 1
• 238000010254 subcutaneous injection Methods 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
• 239000001384 succinic acid Substances 0.000 description 1
• AXOIZCJOOAYSMI-UHFFFAOYSA-N succinylcholine Chemical compound C[N+](C)(C)CCOC(=O)CCC(=O)OCC[N+](C)(C)C AXOIZCJOOAYSMI-UHFFFAOYSA-N 0.000 description 1
• 229940032712 succinylcholine Drugs 0.000 description 1
• 239000005720 sucrose Substances 0.000 description 1
• 150000005846 sugar alcohols Polymers 0.000 description 1
• 150000008163 sugars Chemical class 0.000 description 1
• 125000002653 sulfanylmethyl group Chemical group [H]SC([H])([H])[*] 0.000 description 1
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
• 230000001629 suppression Effects 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 208000024891 symptom Diseases 0.000 description 1
• 210000000225 synapse Anatomy 0.000 description 1
• 230000000946 synaptic effect Effects 0.000 description 1
• 230000006794 tachycardia Effects 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 235000012222 talc Nutrition 0.000 description 1
• 229940095064 tartrate 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
• WFUBKOZDTGFCJO-HTQZYQBOSA-N tert-butyl (1r,5r)-4,7-diazabicyclo[3.2.0]heptane-4-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@H]2NC[C@@H]12 WFUBKOZDTGFCJO-HTQZYQBOSA-N 0.000 description 1
• IKKDUYDJXCENOS-VXGBXAGGSA-N tert-butyl (1r,5r)-7-(6-chloropyridin-3-yl)-4,7-diazabicyclo[3.2.0]heptane-4-carboxylate Chemical compound C([C@@H]1[C@H]2CCN1C(=O)OC(C)(C)C)N2C1=CC=C(Cl)N=C1 IKKDUYDJXCENOS-VXGBXAGGSA-N 0.000 description 1
• QYAYEQNJXBSCAW-HUUCEWRRSA-N tert-butyl (1r,5r)-7-benzyl-4,7-diazabicyclo[3.2.0]heptane-4-carboxylate Chemical compound C([C@@H]1[C@H]2CCN1C(=O)OC(C)(C)C)N2CC1=CC=CC=C1 QYAYEQNJXBSCAW-HUUCEWRRSA-N 0.000 description 1
• JKNUCHVBHOSJED-CHWSQXEVSA-N tert-butyl (1r,5r)-7-pyridin-3-yl-4,7-diazabicyclo[3.2.0]heptane-4-carboxylate Chemical compound C([C@@H]1[C@H]2CCN1C(=O)OC(C)(C)C)N2C1=CC=CN=C1 JKNUCHVBHOSJED-CHWSQXEVSA-N 0.000 description 1
• QUHUQFUNVDCSCL-ZYHUDNBSSA-N tert-butyl (1r,5s)-3-(6-chloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane-6-carboxylate Chemical compound C([C@@H]1CN([C@@H]1C1)C(=O)OC(C)(C)C)N1C1=CC=C(Cl)N=C1 QUHUQFUNVDCSCL-ZYHUDNBSSA-N 0.000 description 1
• FYJPTXIDNMZVBS-TZMCWYRMSA-N tert-butyl (1r,6s)-7-(2-nitrophenyl)sulfonyl-4,7-diazabicyclo[4.2.0]octane-4-carboxylate Chemical compound C([C@H]1CCN(C[C@H]11)C(=O)OC(C)(C)C)N1S(=O)(=O)C1=CC=CC=C1[N+]([O-])=O FYJPTXIDNMZVBS-TZMCWYRMSA-N 0.000 description 1
• HYCRVGBNHOUYBV-JSGCOSHPSA-N tert-butyl (1s,6r)-7-pyridin-3-yl-4,7-diazabicyclo[4.2.0]octane-4-carboxylate Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)OC(C)(C)C)N1C1=CC=CN=C1 HYCRVGBNHOUYBV-JSGCOSHPSA-N 0.000 description 1
• LGEWGFOMLJQHLL-VHSXEESVSA-N tert-butyl (4as,7as)-2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]2CNC[C@@H]12 LGEWGFOMLJQHLL-VHSXEESVSA-N 0.000 description 1
• CXJWLLXWCAVZNN-UHFFFAOYSA-N tert-butyl 2,3-dihydropyrrolo[2,3-c]pyridine-1-carboxylate Chemical compound C1=NC=C2N(C(=O)OC(C)(C)C)CCC2=C1 CXJWLLXWCAVZNN-UHFFFAOYSA-N 0.000 description 1
• HSXLTLXVJGPLHG-UHFFFAOYSA-N tert-butyl 2-hydroxy-2,3-dihydropyrrolo[2,3-c]pyridine-1-carboxylate Chemical compound C1=NC=C2N(C(=O)OC(C)(C)C)C(O)CC2=C1 HSXLTLXVJGPLHG-UHFFFAOYSA-N 0.000 description 1
• FQJRZOYTUCCBQR-UHFFFAOYSA-N tert-butyl 2-methylheptanoate Chemical compound CCCCCC(C)C(=O)OC(C)(C)C FQJRZOYTUCCBQR-UHFFFAOYSA-N 0.000 description 1
• ULXATPSIGBJTPI-UHFFFAOYSA-N tert-butyl 3-hydroxy-4-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CO)C(O)C1 ULXATPSIGBJTPI-UHFFFAOYSA-N 0.000 description 1
• DIHCQPPXAIYZOO-UHFFFAOYSA-N tert-butyl n-(4-methylpyridin-3-yl)carbamate Chemical compound CC1=CC=NC=C1NC(=O)OC(C)(C)C DIHCQPPXAIYZOO-UHFFFAOYSA-N 0.000 description 1
• 150000003512 tertiary amines Chemical class 0.000 description 1
• 239000012085 test solution Substances 0.000 description 1
• CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
• 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
• 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
• QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
• 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
• 150000003536 tetrazoles Chemical class 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• 229940124597 therapeutic agent Drugs 0.000 description 1
• 230000004797 therapeutic response Effects 0.000 description 1
• 125000005304 thiadiazolidinyl group Chemical group 0.000 description 1
• 125000005305 thiadiazolinyl group Chemical group 0.000 description 1
• 125000001984 thiazolidinyl group Chemical group 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
• 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
• BJBUEDPLEOHJGE-IMJSIDKUSA-N trans-3-hydroxy-L-proline Chemical compound O[C@H]1CC[NH2+][C@@H]1C([O-])=O BJBUEDPLEOHJGE-IMJSIDKUSA-N 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 238000000844 transformation Methods 0.000 description 1
• 229910052723 transition metal Inorganic materials 0.000 description 1
• 150000003624 transition metals Chemical class 0.000 description 1
• 230000008733 trauma Effects 0.000 description 1
• 238000011269 treatment regimen Methods 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• 125000001425 triazolyl group Chemical group 0.000 description 1
• QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
• SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
• CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical compound C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
• 125000005455 trithianyl group Chemical group 0.000 description 1
• 230000036269 ulceration Effects 0.000 description 1
• 235000015112 vegetable and seed oil Nutrition 0.000 description 1
• 239000008158 vegetable oil Substances 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 238000005406 washing Methods 0.000 description 1
• 238000005303 weighing Methods 0.000 description 1
• 230000037303 wrinkles Effects 0.000 description 1
• 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1