JP2002370976A - うつ病及び不安のための併合療法 - Google Patents

Info

Publication number

JP2002370976A

JP2002370976A JP2002141515A JP2002141515A JP2002370976A JP 2002370976 A JP2002370976 A JP 2002370976A JP 2002141515 A JP2002141515 A JP 2002141515A JP 2002141515 A JP2002141515 A JP 2002141515A JP 2002370976 A JP2002370976 A JP 2002370976A

Authority

JP

Japan

Prior art keywords

dichlorophenoxy

methylamine

alkyl

formula

compound

Prior art date

2001-05-23

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.)

Withdrawn

Links

• Espacenet
• Global Dossier
• Discuss

• 208000019901 Anxiety disease Diseases 0.000 title claims abstract description 91
• 230000036506 anxiety Effects 0.000 title claims abstract description 85
• 238000002648 combination therapy Methods 0.000 title description 3
• 238000011282 treatment Methods 0.000 claims abstract description 66
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 54
• 239000000203 mixture Substances 0.000 claims abstract description 49
• 229940087102 Dopamine D3 receptor agonist Drugs 0.000 claims abstract description 33
• 239000002298 dopamine 3 receptor stimulating agent Substances 0.000 claims abstract description 33
• 241000124008 Mammalia Species 0.000 claims abstract description 17
• 150000001875 compounds Chemical class 0.000 claims description 181
• 150000003839 salts Chemical class 0.000 claims description 83
• -1 cyano, nitro, amino, Hydroxy, carbonyl Chemical group 0.000 claims description 77
• 229910052739 hydrogen Inorganic materials 0.000 claims description 50
• 208000020401 Depressive disease Diseases 0.000 claims description 49
• 239000001257 hydrogen Substances 0.000 claims description 49
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 45
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 29
• 229910052757 nitrogen Inorganic materials 0.000 claims description 28
• 125000005842 heteroatom Chemical group 0.000 claims description 24
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 23
• 229910052799 carbon Inorganic materials 0.000 claims description 20
• 125000001153 fluoro group Chemical group F* 0.000 claims description 20
• 125000001624 naphthyl group Chemical group 0.000 claims description 19
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
• 239000013543 active substance Substances 0.000 claims description 17
• 125000000217 alkyl group Chemical group 0.000 claims description 17
• 125000005843 halogen group Chemical group 0.000 claims description 16
• 230000000694 effects Effects 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 125000001424 substituent group Chemical group 0.000 claims description 14
• 150000002431 hydrogen Chemical class 0.000 claims description 13
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• 239000003937 drug carrier Substances 0.000 claims description 11
• 239000001301 oxygen Substances 0.000 claims description 11
• 229910052717 sulfur Inorganic materials 0.000 claims description 11
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
• 150000001721 carbon Chemical group 0.000 claims description 9
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• 229920006395 saturated elastomer Polymers 0.000 claims description 8
• 239000011593 sulfur Substances 0.000 claims description 8
• 230000027455 binding Effects 0.000 claims description 7
• 125000001072 heteroaryl group Chemical group 0.000 claims description 7
• 125000000623 heterocyclic group Chemical group 0.000 claims description 7
• 125000003282 alkyl amino group Chemical group 0.000 claims description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
• HYLYTRKKGFVHIE-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-fluorophenyl]-n-methylethanamine Chemical compound CNC(C)C1=CC(F)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 HYLYTRKKGFVHIE-UHFFFAOYSA-N 0.000 claims description 5
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
• XQFSLGJDGVQPGP-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenoxy)-5-fluorophenyl]pyrrolidine Chemical compound C1CCNC1C1=CC(F)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 XQFSLGJDGVQPGP-UHFFFAOYSA-N 0.000 claims description 4
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 125000002837 carbocyclic group Chemical group 0.000 claims description 4
• 125000004434 sulfur atom Chemical group 0.000 claims description 4
• 125000004429 atom Chemical group 0.000 claims description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
• NPJYROQKHDJYRQ-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-4,5-dimethylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C)=C(C)C=C1OC1=CC=C(Cl)C(Cl)=C1 NPJYROQKHDJYRQ-UHFFFAOYSA-N 0.000 claims description 2
• SOCXCXJYEMOKAM-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-4-(1,2,4-triazol-1-yl)phenyl]-n-methylethanamine Chemical compound CNC(C)C1=CC=C(N2N=CN=C2)C=C1OC1=CC=C(Cl)C(Cl)=C1 SOCXCXJYEMOKAM-UHFFFAOYSA-N 0.000 claims description 2
• LLVVRQNZUNMHJV-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-4-(furan-2-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC=C(C=2OC=CC=2)C=C1OC1=CC=C(Cl)C(Cl)=C1 LLVVRQNZUNMHJV-UHFFFAOYSA-N 0.000 claims description 2
• AAQZZAVVFRIEOD-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-4-(trifluoromethyl)phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=C(C(F)(F)F)C=C1OC1=CC=C(Cl)C(Cl)=C1 AAQZZAVVFRIEOD-UHFFFAOYSA-N 0.000 claims description 2
• BWBOBCUPLKYBOV-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-4-methoxyphenyl]-n,n-dimethylmethanamine Chemical compound COC1=CC=C(CN(C)C)C(OC=2C=C(Cl)C(Cl)=CC=2)=C1 BWBOBCUPLKYBOV-UHFFFAOYSA-N 0.000 claims description 2
• KBGXEJXXNBUUKO-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-4-phenylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC=C(C=2C=CC=CC=2)C=C1OC1=CC=C(Cl)C(Cl)=C1 KBGXEJXXNBUUKO-UHFFFAOYSA-N 0.000 claims description 2
• SFTJBUCEUIKDJD-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-4-thiophen-3-ylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC=C(C2=CSC=C2)C=C1OC1=CC=C(Cl)C(Cl)=C1 SFTJBUCEUIKDJD-UHFFFAOYSA-N 0.000 claims description 2
• IQGWBOYXUSLCFT-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(1,2,4-triazol-4-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(N2C=NN=C2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 IQGWBOYXUSLCFT-UHFFFAOYSA-N 0.000 claims description 2
• QLTUAGOAYVRRPQ-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(1,3-thiazol-2-yl)phenyl]-n-methylethanamine Chemical compound CNC(C)C1=CC(C=2SC=CN=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 QLTUAGOAYVRRPQ-UHFFFAOYSA-N 0.000 claims description 2
• APMXCCUBPMTTLK-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(1,3-thiazol-2-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2SC=CN=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 APMXCCUBPMTTLK-UHFFFAOYSA-N 0.000 claims description 2
• MRHLSXLWXQUUIW-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(4-methylphenyl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2C=CC(C)=CC=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 MRHLSXLWXQUUIW-UHFFFAOYSA-N 0.000 claims description 2
• JMPDXZXUFVZHHI-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(furan-2-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2OC=CC=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 JMPDXZXUFVZHHI-UHFFFAOYSA-N 0.000 claims description 2
• ULJOCBVUVYUVEY-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(triazol-2-yl)phenyl]-n-methylethanamine Chemical compound CNC(C)C1=CC(N2N=CC=N2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 ULJOCBVUVYUVEY-UHFFFAOYSA-N 0.000 claims description 2
• MGHGKQQYNNPDLG-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(triazol-2-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(N2N=CC=N2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 MGHGKQQYNNPDLG-UHFFFAOYSA-N 0.000 claims description 2
• YJHCOYWCYPKAQN-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(trifluoromethyl)phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC(C(F)(F)F)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 YJHCOYWCYPKAQN-UHFFFAOYSA-N 0.000 claims description 2
• MCCUQEYBDREHCZ-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-fluorophenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC(F)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 MCCUQEYBDREHCZ-UHFFFAOYSA-N 0.000 claims description 2
• SHXLCIMINLRWNL-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-methoxyphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(OC)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 SHXLCIMINLRWNL-UHFFFAOYSA-N 0.000 claims description 2
• ARYNSJMHZVVGNH-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-methylphenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC(C)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 ARYNSJMHZVVGNH-UHFFFAOYSA-N 0.000 claims description 2
• JPBFWBNMQFVEEC-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-pyridin-3-ylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2C=NC=CC=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 JPBFWBNMQFVEEC-UHFFFAOYSA-N 0.000 claims description 2
• JERYDYFQMRCTFJ-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-pyridin-4-ylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2C=CN=CC=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 JERYDYFQMRCTFJ-UHFFFAOYSA-N 0.000 claims description 2
• MFVLUIJGQADSJH-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-thiophen-2-ylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2SC=CC=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 MFVLUIJGQADSJH-UHFFFAOYSA-N 0.000 claims description 2
• QFDTVBGMNGXZGK-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)phenyl]-n,n-dimethylethanamine Chemical compound CN(C)C(C)C1=CC=CC=C1OC1=CC=C(Cl)C(Cl)=C1 QFDTVBGMNGXZGK-UHFFFAOYSA-N 0.000 claims description 2
• HJIWIMXZBPSSTO-UHFFFAOYSA-N 1-[2-(3-chloro-4-fluorophenoxy)-5-fluorophenyl]-n-methylmethanamine Chemical compound CNCC1=CC(F)=CC=C1OC1=CC=C(F)C(Cl)=C1 HJIWIMXZBPSSTO-UHFFFAOYSA-N 0.000 claims description 2
• PMXOUAJLQYBUOO-UHFFFAOYSA-N 1-[2-(4-chlorophenoxy)-5-fluorophenyl]-n-methylmethanamine Chemical compound CNCC1=CC(F)=CC=C1OC1=CC=C(Cl)C=C1 PMXOUAJLQYBUOO-UHFFFAOYSA-N 0.000 claims description 2
• MNHWUSSFFCLNEP-UHFFFAOYSA-N 1-[2-(4-chlorophenoxy)phenyl]-n-methylethanamine Chemical compound CNC(C)C1=CC=CC=C1OC1=CC=C(Cl)C=C1 MNHWUSSFFCLNEP-UHFFFAOYSA-N 0.000 claims description 2
• FZCQKTZYKUFNAJ-UHFFFAOYSA-N 1-[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]pyrazol-3-amine Chemical compound CNCC1=CC(N2N=C(N)C=C2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 FZCQKTZYKUFNAJ-UHFFFAOYSA-N 0.000 claims description 2
• KGEKHVCIFGADFG-UHFFFAOYSA-N 1-[4-chloro-2-(3,4-dichlorophenoxy)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC=C(Cl)C=C1OC1=CC=C(Cl)C(Cl)=C1 KGEKHVCIFGADFG-UHFFFAOYSA-N 0.000 claims description 2
• TYLANFGUNBMRFO-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenoxy)-5-fluorophenyl]-1-methylpyrrolidine Chemical compound CN1CCCC1C1=CC(F)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 TYLANFGUNBMRFO-UHFFFAOYSA-N 0.000 claims description 2
• QFWNAKAETMKRTM-UHFFFAOYSA-N 3-(3,4-dichlorophenoxy)-4-(methylaminomethyl)benzonitrile Chemical compound CNCC1=CC=C(C#N)C=C1OC1=CC=C(Cl)C(Cl)=C1 QFWNAKAETMKRTM-UHFFFAOYSA-N 0.000 claims description 2
• ZPJJDPPFWWSPPB-UHFFFAOYSA-N 4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)benzonitrile Chemical compound CNCC1=CC(C#N)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 ZPJJDPPFWWSPPB-UHFFFAOYSA-N 0.000 claims description 2
• GQNWCHJJMVQERW-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]phenyl]acetamide Chemical compound CNCC1=CC(C=2C=C(NC(C)=O)C=CC=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 GQNWCHJJMVQERW-UHFFFAOYSA-N 0.000 claims description 2
• KZLLRXARLPOUMH-UHFFFAOYSA-N n-[4-(3,4-dichlorophenoxy)-3-[(dimethylamino)methyl]phenyl]acetamide Chemical compound CN(C)CC1=CC(NC(C)=O)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 KZLLRXARLPOUMH-UHFFFAOYSA-N 0.000 claims description 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
• XNKUKCFVELTTTO-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-4,5-dimethoxyphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(OC)=C(OC)C=C1OC1=CC=C(Cl)C(Cl)=C1 XNKUKCFVELTTTO-UHFFFAOYSA-N 0.000 claims 1
• DKXDRPCDKRMICS-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-4-methoxyphenyl]-n-methylmethanamine Chemical compound CNCC1=CC=C(OC)C=C1OC1=CC=C(Cl)C(Cl)=C1 DKXDRPCDKRMICS-UHFFFAOYSA-N 0.000 claims 1
• WKOZOESISFTQMB-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(5-methylthiophen-2-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2SC(C)=CC=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 WKOZOESISFTQMB-UHFFFAOYSA-N 0.000 claims 1
• KCRBGCHPNCBUCW-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-phenylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2C=CC=CC=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 KCRBGCHPNCBUCW-UHFFFAOYSA-N 0.000 claims 1
• GKVABNNXZNUTSR-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-thiophen-3-ylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C2=CSC=C2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 GKVABNNXZNUTSR-UHFFFAOYSA-N 0.000 claims 1
• LWHZIZQQEKJCCP-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)phenyl]-n-methylethanamine Chemical compound CNC(C)C1=CC=CC=C1OC1=CC=C(Cl)C(Cl)=C1 LWHZIZQQEKJCCP-UHFFFAOYSA-N 0.000 claims 1
• WJHPAIHCWWZGFM-UHFFFAOYSA-N 1-[2-(4-chlorophenoxy)-5-fluorophenyl]-n-methylethanamine Chemical compound CNC(C)C1=CC(F)=CC=C1OC1=CC=C(Cl)C=C1 WJHPAIHCWWZGFM-UHFFFAOYSA-N 0.000 claims 1
• XAGZJIQIVXSURR-UHFFFAOYSA-N 1-[4-(trifluoromethyl)phenyl]piperidin-2-one Chemical compound C1=CC(C(F)(F)F)=CC=C1N1C(=O)CCCC1 XAGZJIQIVXSURR-UHFFFAOYSA-N 0.000 claims 1
• WJQHBBMQIFJYHD-UHFFFAOYSA-N 1-[4-bromo-2-(3,4-dichlorophenoxy)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC=C(Br)C=C1OC1=CC=C(Cl)C(Cl)=C1 WJQHBBMQIFJYHD-UHFFFAOYSA-N 0.000 claims 1
• HGYIZARFFWEFEA-UHFFFAOYSA-N CC(C(C=C(C(CCN1C(C=C2)=CC(CNC)=C2OC(C=C2)=CC(Cl)=C2Cl)C1=O)C=C1)=C1OC(C=C1)=CC(Cl)=C1Cl)NC Chemical compound CC(C(C=C(C(CCN1C(C=C2)=CC(CNC)=C2OC(C=C2)=CC(Cl)=C2Cl)C1=O)C=C1)=C1OC(C=C1)=CC(Cl)=C1Cl)NC HGYIZARFFWEFEA-UHFFFAOYSA-N 0.000 claims 1
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
• 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 96
• 230000000407 monoamine reuptake Effects 0.000 abstract description 22
• 230000001225 therapeutic effect Effects 0.000 abstract description 4
• 230000003449 preventive effect Effects 0.000 abstract 2
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 42
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 34
• SYJXFKPQNSDJLI-HKEUSBCWSA-N neamine Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](N)C[C@@H]1N SYJXFKPQNSDJLI-HKEUSBCWSA-N 0.000 description 32
• 208000035475 disorder Diseases 0.000 description 26
• 239000000543 intermediate Substances 0.000 description 26
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
• 238000003786 synthesis reaction Methods 0.000 description 22
• 239000003814 drug Substances 0.000 description 21
• 239000003112 inhibitor Substances 0.000 description 21
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 20
• 238000006243 chemical reaction Methods 0.000 description 17
• 201000010099 disease Diseases 0.000 description 16
• 239000002253 acid Substances 0.000 description 15
• 229940044601 receptor agonist Drugs 0.000 description 14
• 239000000018 receptor agonist Substances 0.000 description 14
• 102000004073 Dopamine D3 Receptors Human genes 0.000 description 13
• 108090000525 Dopamine D3 Receptors Proteins 0.000 description 13
• 239000002585 base Substances 0.000 description 13
• 230000015572 biosynthetic process Effects 0.000 description 13
• 229940124597 therapeutic agent Drugs 0.000 description 13
• 239000000243 solution Substances 0.000 description 12
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
• 210000004027 cell Anatomy 0.000 description 11
• 229940126403 monoamine reuptake inhibitor Drugs 0.000 description 11
• 239000000126 substance Substances 0.000 description 11
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
• 150000001299 aldehydes Chemical group 0.000 description 10
• 229960003638 dopamine Drugs 0.000 description 10
• 239000002904 solvent Substances 0.000 description 10
• XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 10
• SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 9
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
• 241001465754 Metazoa Species 0.000 description 9
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 9
• 229960002748 norepinephrine Drugs 0.000 description 9
• 208000019906 panic disease Diseases 0.000 description 9
• 238000002360 preparation method Methods 0.000 description 9
• 239000003826 tablet Substances 0.000 description 9
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
• 206010034912 Phobia Diseases 0.000 description 8
• 239000000460 chlorine Substances 0.000 description 8
• 239000000839 emulsion Substances 0.000 description 8
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 7
• 239000002249 anxiolytic agent Substances 0.000 description 7
• 239000003153 chemical reaction reagent Substances 0.000 description 7
• 125000004122 cyclic group Chemical group 0.000 description 7
• UHSKFQJFRQCDBE-UHFFFAOYSA-N ropinirole Chemical compound CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2 UHSKFQJFRQCDBE-UHFFFAOYSA-N 0.000 description 7
• 229940076279 serotonin Drugs 0.000 description 7
• KORNTPPJEAJQIU-KJXAQDMKSA-N Cabaser Chemical compound C1=CC([C@H]2C[C@H](CN(CC=C)[C@@H]2C2)C(=O)N(CCCN(C)C)C(=O)NCC)=C3C2=CNC3=C1 KORNTPPJEAJQIU-KJXAQDMKSA-N 0.000 description 6
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• 230000000949 anxiolytic effect Effects 0.000 description 6
• 125000003118 aryl group Chemical group 0.000 description 6
• 150000003857 carboxamides Chemical class 0.000 description 6
• 150000002576 ketones Chemical class 0.000 description 6
• 150000003951 lactams Chemical class 0.000 description 6
• 150000002825 nitriles Chemical class 0.000 description 6
• 231100000252 nontoxic Toxicity 0.000 description 6
• 230000003000 nontoxic effect Effects 0.000 description 6
• FASDKYOPVNHBLU-ZETCQYMHSA-N pramipexole Chemical compound C1[C@@H](NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-ZETCQYMHSA-N 0.000 description 6
• 230000009467 reduction Effects 0.000 description 6
• 238000006722 reduction reaction Methods 0.000 description 6
• 201000001716 specific phobia Diseases 0.000 description 6
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
• 241000282412 Homo Species 0.000 description 5
• 206010033664 Panic attack Diseases 0.000 description 5
• 206010041250 Social phobia Diseases 0.000 description 5
• 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 5
• 229930006000 Sucrose Natural products 0.000 description 5
• 239000007983 Tris buffer Substances 0.000 description 5
• 150000001412 amines Chemical class 0.000 description 5
• 239000000872 buffer Substances 0.000 description 5
• 239000003795 chemical substances by application Substances 0.000 description 5
• 229910052801 chlorine Inorganic materials 0.000 description 5
• 239000002552 dosage form Substances 0.000 description 5
• 208000024714 major depressive disease Diseases 0.000 description 5
• 125000006239 protecting group Chemical group 0.000 description 5
• 239000011734 sodium Substances 0.000 description 5
• 239000005720 sucrose Substances 0.000 description 5
• 238000012360 testing method Methods 0.000 description 5
• 210000001519 tissue Anatomy 0.000 description 5
• 230000009466 transformation Effects 0.000 description 5
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• 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 4
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
• 239000000935 antidepressant agent Substances 0.000 description 4
• 229940005513 antidepressants Drugs 0.000 description 4
• 229940005530 anxiolytics Drugs 0.000 description 4
• 230000008901 benefit Effects 0.000 description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
• 229910052794 bromium Inorganic materials 0.000 description 4
• 229960004596 cabergoline Drugs 0.000 description 4
• ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 4
• 239000003085 diluting agent Substances 0.000 description 4
• 208000024732 dysthymic disease Diseases 0.000 description 4
• 238000002347 injection Methods 0.000 description 4
• 239000007924 injection Substances 0.000 description 4
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
• 239000000463 material Substances 0.000 description 4
• 239000002609 medium Substances 0.000 description 4
• 208000015238 neurotic disease Diseases 0.000 description 4
• 239000003921 oil Substances 0.000 description 4
• 235000019198 oils Nutrition 0.000 description 4
• 239000006187 pill Substances 0.000 description 4
• 230000002265 prevention Effects 0.000 description 4
• 230000002829 reductive effect Effects 0.000 description 4
• 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 4
• 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 4
• 239000008247 solid mixture Substances 0.000 description 4
• 239000004094 surface-active agent Substances 0.000 description 4
• 239000000725 suspension Substances 0.000 description 4
• 210000003568 synaptosome Anatomy 0.000 description 4
• 230000001960 triggered effect Effects 0.000 description 4
• 239000003981 vehicle Substances 0.000 description 4
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
• 229940094659 Dopamine reuptake inhibitor Drugs 0.000 description 3
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
• 208000019022 Mood disease Diseases 0.000 description 3
• 241000700159 Rattus Species 0.000 description 3
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
• 150000007513 acids Chemical class 0.000 description 3
• 230000009471 action Effects 0.000 description 3
• 239000004480 active ingredient Substances 0.000 description 3
• 239000007864 aqueous solution Substances 0.000 description 3
• 239000007900 aqueous suspension Substances 0.000 description 3
• 238000003556 assay Methods 0.000 description 3
• 125000002618 bicyclic heterocycle group Chemical group 0.000 description 3
• 239000002775 capsule Substances 0.000 description 3
• 239000003638 chemical reducing agent Substances 0.000 description 3
• 125000001309 chloro group Chemical group Cl* 0.000 description 3
• 239000000221 dopamine uptake inhibitor Substances 0.000 description 3
• 229940079593 drug Drugs 0.000 description 3
• 238000005516 engineering process Methods 0.000 description 3
• 150000002148 esters Chemical class 0.000 description 3
• 239000011737 fluorine Substances 0.000 description 3
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
• 238000011534 incubation Methods 0.000 description 3
• 239000012442 inert solvent Substances 0.000 description 3
• 239000007788 liquid Substances 0.000 description 3
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
• 239000000546 pharmaceutical excipient Substances 0.000 description 3
• 208000019899 phobic disease Diseases 0.000 description 3
• 150000003904 phospholipids Chemical class 0.000 description 3
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
• 239000000843 powder Substances 0.000 description 3
• 229960003089 pramipexole Drugs 0.000 description 3
• 229940002612 prodrug Drugs 0.000 description 3
• 239000000651 prodrug Substances 0.000 description 3
• 229960001879 ropinirole Drugs 0.000 description 3
• 239000008159 sesame oil Substances 0.000 description 3
• 235000011803 sesame oil Nutrition 0.000 description 3
• 229910052708 sodium Inorganic materials 0.000 description 3
• 239000006228 supernatant Substances 0.000 description 3
• 150000003536 tetrazoles Chemical class 0.000 description 3
• 238000000844 transformation Methods 0.000 description 3
• KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 2
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
• QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 2
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
• 208000008811 Agoraphobia Diseases 0.000 description 2
• 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 2
• 208000020925 Bipolar disease Diseases 0.000 description 2
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
• 108010078791 Carrier Proteins Proteins 0.000 description 2
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
• 208000007590 Disorders of Excessive Somnolence Diseases 0.000 description 2
• 108010010803 Gelatin Proteins 0.000 description 2
• 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 2
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
• 101000879758 Homo sapiens Sjoegren syndrome nuclear autoantigen 1 Proteins 0.000 description 2
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
• 240000007472 Leucaena leucocephala Species 0.000 description 2
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
• 229910019142 PO4 Inorganic materials 0.000 description 2
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
• 235000019483 Peanut oil Nutrition 0.000 description 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
• 229920002873 Polyethylenimine Polymers 0.000 description 2
• 206010036618 Premenstrual syndrome Diseases 0.000 description 2
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
• 206010039897 Sedation Diseases 0.000 description 2
• 201000001880 Sexual dysfunction Diseases 0.000 description 2
• 102100037330 Sjoegren syndrome nuclear autoantigen 1 Human genes 0.000 description 2
• 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 2
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
• 102100033928 Sodium-dependent dopamine transporter Human genes 0.000 description 2
• 229920002472 Starch Polymers 0.000 description 2
• 238000010521 absorption reaction Methods 0.000 description 2
• 230000002378 acidificating effect Effects 0.000 description 2
• 230000010933 acylation Effects 0.000 description 2
• 238000005917 acylation reaction Methods 0.000 description 2
• 230000006978 adaptation Effects 0.000 description 2
• 239000000556 agonist Substances 0.000 description 2
• 235000010443 alginic acid Nutrition 0.000 description 2
• 229920000615 alginic acid Polymers 0.000 description 2
• 229910052783 alkali metal Inorganic materials 0.000 description 2
• 125000003342 alkenyl group Chemical group 0.000 description 2
• 229940025084 amphetamine Drugs 0.000 description 2
• 230000001430 anti-depressive effect Effects 0.000 description 2
• 229940049706 benzodiazepine Drugs 0.000 description 2
• YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
• 239000007853 buffer solution Substances 0.000 description 2
• RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
• 239000001506 calcium phosphate Substances 0.000 description 2
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
• 239000000969 carrier Substances 0.000 description 2
• 239000003054 catalyst Substances 0.000 description 2
• 150000001768 cations Chemical class 0.000 description 2
• 229960003920 cocaine Drugs 0.000 description 2
• 235000012343 cottonseed oil Nutrition 0.000 description 2
• 239000002385 cottonseed oil Substances 0.000 description 2
• 150000003950 cyclic amides Chemical class 0.000 description 2
• USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
• 239000012055 enteric layer Substances 0.000 description 2
• 229950008087 etrabamine Drugs 0.000 description 2
• 238000002474 experimental method Methods 0.000 description 2
• 235000019197 fats Nutrition 0.000 description 2
• 239000000945 filler Substances 0.000 description 2
• 238000001914 filtration Methods 0.000 description 2
• 238000009472 formulation Methods 0.000 description 2
• 230000006870 function Effects 0.000 description 2
• 229920000159 gelatin Polymers 0.000 description 2
• 239000008273 gelatin Substances 0.000 description 2
• 235000019322 gelatine Nutrition 0.000 description 2
• 235000011852 gelatine desserts Nutrition 0.000 description 2
• 239000011521 glass Substances 0.000 description 2
• 239000008103 glucose Substances 0.000 description 2
• 235000011187 glycerol Nutrition 0.000 description 2
• 239000000380 hallucinogen Substances 0.000 description 2
• 238000004128 high performance liquid chromatography Methods 0.000 description 2
• 150000002430 hydrocarbons Chemical group 0.000 description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
• 206010020765 hypersomnia Diseases 0.000 description 2
• 239000003326 hypnotic agent Substances 0.000 description 2
• 230000000147 hypnotic effect Effects 0.000 description 2
• 238000000338 in vitro Methods 0.000 description 2
• 238000001727 in vivo Methods 0.000 description 2
• 239000004615 ingredient Substances 0.000 description 2
• 206010022437 insomnia Diseases 0.000 description 2
• 229910052740 iodine Inorganic materials 0.000 description 2
• 239000011630 iodine Substances 0.000 description 2
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
• 239000008101 lactose Substances 0.000 description 2
• 229910052744 lithium Inorganic materials 0.000 description 2
• 239000012280 lithium aluminium hydride Substances 0.000 description 2
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
• 235000019359 magnesium stearate Nutrition 0.000 description 2
• 230000002503 metabolic effect Effects 0.000 description 2
• 210000003205 muscle Anatomy 0.000 description 2
• 238000002663 nebulization Methods 0.000 description 2
• 239000006186 oral dosage form Substances 0.000 description 2
• 239000003960 organic solvent Substances 0.000 description 2
• 239000000312 peanut oil Substances 0.000 description 2
• 239000008188 pellet Substances 0.000 description 2
• 230000000144 pharmacologic effect Effects 0.000 description 2
• JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 2
• 229950010883 phencyclidine Drugs 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
• 239000010452 phosphate Substances 0.000 description 2
• 239000002798 polar solvent Substances 0.000 description 2
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
• 230000002028 premature Effects 0.000 description 2
• 239000000047 product Substances 0.000 description 2
• RXWNCPJZOCPEPQ-NVWDDTSBSA-N puromycin Chemical compound C1=CC(OC)=CC=C1C[C@H](N)C(=O)N[C@H]1[C@@H](O)[C@H](N2C3=NC=NC(=C3N=C2)N(C)C)O[C@@H]1CO RXWNCPJZOCPEPQ-NVWDDTSBSA-N 0.000 description 2
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
• XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
• 230000007115 recruitment Effects 0.000 description 2
• 230000029058 respiratory gaseous exchange Effects 0.000 description 2
• 230000004044 response Effects 0.000 description 2
• 238000012552 review Methods 0.000 description 2
• 102220240796 rs553605556 Human genes 0.000 description 2
• 229940125723 sedative agent Drugs 0.000 description 2
• 239000000932 sedative agent Substances 0.000 description 2
• 231100000872 sexual dysfunction Toxicity 0.000 description 2
• 239000012279 sodium borohydride Substances 0.000 description 2
• 229910000033 sodium borohydride Inorganic materials 0.000 description 2
• 239000007787 solid Substances 0.000 description 2
• 239000003549 soybean oil Substances 0.000 description 2
• 235000012424 soybean oil Nutrition 0.000 description 2
• 239000008107 starch Substances 0.000 description 2
• 235000019698 starch Nutrition 0.000 description 2
• 239000000829 suppository Substances 0.000 description 2
• 239000000375 suspending agent Substances 0.000 description 2
• 208000024891 symptom Diseases 0.000 description 2
• 239000000454 talc Substances 0.000 description 2
• 229910052623 talc Inorganic materials 0.000 description 2
• 238000002560 therapeutic procedure Methods 0.000 description 2
• 229930192474 thiophene Natural products 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
• 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
• 208000016261 weight loss Diseases 0.000 description 2
• 230000004580 weight loss Effects 0.000 description 2
• XDIYNQZUNSSENW-UUBOPVPUSA-N (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O XDIYNQZUNSSENW-UUBOPVPUSA-N 0.000 description 1
• LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
• NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
• BLYMJBIZMIGWFK-HNNXBMFYSA-N (7s)-7-(dipropylamino)-5,6,7,8-tetrahydronaphthalen-2-ol Chemical compound C1=C(O)C=C2C[C@@H](N(CCC)CCC)CCC2=C1 BLYMJBIZMIGWFK-HNNXBMFYSA-N 0.000 description 1
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 1
• BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
• YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
• CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
• KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
• BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
• JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 1
• OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
• FWIKQRIGKMEJCZ-UHFFFAOYSA-N 1,5,5-trimethyl-3-[3-(methylaminomethyl)-4-naphthalen-2-yloxyphenyl]imidazolidine-2,4-dione Chemical compound C=1C=C(OC=2C=C3C=CC=CC3=CC=2)C(CNC)=CC=1N1C(=O)N(C)C(C)(C)C1=O FWIKQRIGKMEJCZ-UHFFFAOYSA-N 0.000 description 1
• UBHFJRNWKGLSAW-UHFFFAOYSA-N 1-(5-imidazol-1-yl-2-naphthalen-2-yloxyphenyl)-n,n-dimethylmethanamine Chemical compound C=1C=C(OC=2C=C3C=CC=CC3=CC=2)C(CN(C)C)=CC=1N1C=CN=C1 UBHFJRNWKGLSAW-UHFFFAOYSA-N 0.000 description 1
• WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
• ONXYECUKUIZIBT-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-4-(trifluoromethyl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC=C(C(F)(F)F)C=C1OC1=CC=C(Cl)C(Cl)=C1 ONXYECUKUIZIBT-UHFFFAOYSA-N 0.000 description 1
• YMZHLLFBCASHHB-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-4-thiophen-2-ylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC=C(C=2SC=CC=2)C=C1OC1=CC=C(Cl)C(Cl)=C1 YMZHLLFBCASHHB-UHFFFAOYSA-N 0.000 description 1
• CBVMSOILTQVWFP-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(1-methyltetrazol-5-yl)phenyl]-n,n-dimethylethanamine Chemical compound CN(C)C(C)C1=CC(C=2N(N=NN=2)C)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 CBVMSOILTQVWFP-UHFFFAOYSA-N 0.000 description 1
• WXXHYSUXKJDTST-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(2,4-dimethyl-1,3-oxazol-5-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C2=C(N=C(C)O2)C)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 WXXHYSUXKJDTST-UHFFFAOYSA-N 0.000 description 1
• PEPTYCHVMFPBAC-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(2,4-dimethyl-1,3-thiazol-5-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C2=C(N=C(C)S2)C)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 PEPTYCHVMFPBAC-UHFFFAOYSA-N 0.000 description 1
• JABQUIZMMQYOSN-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(2,5-dimethyl-1,3-oxazol-4-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C2=C(OC(C)=N2)C)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 JABQUIZMMQYOSN-UHFFFAOYSA-N 0.000 description 1
• ZWZQQLDJGYCSNM-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(2-methyl-1,3-oxazol-4-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2N=C(C)OC=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 ZWZQQLDJGYCSNM-UHFFFAOYSA-N 0.000 description 1
• LYRAGSVEZOIZJQ-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(2h-tetrazol-5-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2NN=NN=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 LYRAGSVEZOIZJQ-UHFFFAOYSA-N 0.000 description 1
• PKHRKDRVHZSLNS-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(3-methyl-1,2,4-triazol-1-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(N2N=C(C)N=C2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 PKHRKDRVHZSLNS-UHFFFAOYSA-N 0.000 description 1
• YBRZJOAUFIOPTO-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2N=C(C)ON=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 YBRZJOAUFIOPTO-UHFFFAOYSA-N 0.000 description 1
• OXRNPVDIOGPJKD-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(5-methyl-1,2,4-thiadiazol-3-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2N=C(C)SN=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 OXRNPVDIOGPJKD-UHFFFAOYSA-N 0.000 description 1
• WDOHSBCURHURPV-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(triazol-1-yl)phenyl]-n-methylethanamine Chemical compound CNC(C)C1=CC(N2N=NC=C2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 WDOHSBCURHURPV-UHFFFAOYSA-N 0.000 description 1
• VXVOMNFSZSXTSE-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(trifluoromethyl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C(F)(F)F)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 VXVOMNFSZSXTSE-UHFFFAOYSA-N 0.000 description 1
• IBQGQTKTKQIZKP-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-fluoro-4-methoxyphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(F)=C(OC)C=C1OC1=CC=C(Cl)C(Cl)=C1 IBQGQTKTKQIZKP-UHFFFAOYSA-N 0.000 description 1
• ZCVNOEOEWIYCOB-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-fluorophenyl]-n-methylcyclopentan-1-amine Chemical compound C=1C(F)=CC=C(OC=2C=C(Cl)C(Cl)=CC=2)C=1C1(NC)CCCC1 ZCVNOEOEWIYCOB-UHFFFAOYSA-N 0.000 description 1
• FTANDNLTKJAUPS-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-methylsulfanylphenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC(SC)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 FTANDNLTKJAUPS-UHFFFAOYSA-N 0.000 description 1
• GPMJGIFHVAAPIF-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-methylsulfanylphenyl]-n-methylethanamine Chemical compound CNC(C)C1=CC(SC)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 GPMJGIFHVAAPIF-UHFFFAOYSA-N 0.000 description 1
• JXTAAJFTLZKFRN-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-methylsulfanylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(SC)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 JXTAAJFTLZKFRN-UHFFFAOYSA-N 0.000 description 1
• CHTPKHGDXWZUTL-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-methylsulfonylphenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC(S(C)(=O)=O)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 CHTPKHGDXWZUTL-UHFFFAOYSA-N 0.000 description 1
• RXGFZYPOCJFADA-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-methylsulfonylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(S(C)(=O)=O)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 RXGFZYPOCJFADA-UHFFFAOYSA-N 0.000 description 1
• GYCBKZNSUCHHNE-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-propan-2-ylsulfonylphenyl]-n-methylethanamine Chemical compound CNC(C)C1=CC(S(=O)(=O)C(C)C)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 GYCBKZNSUCHHNE-UHFFFAOYSA-N 0.000 description 1
• BQNFBRSSJAIQIR-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-propan-2-ylsulfonylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(S(=O)(=O)C(C)C)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 BQNFBRSSJAIQIR-UHFFFAOYSA-N 0.000 description 1
• NLTGIMKNKKMQPE-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-pyridin-2-ylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2N=CC=CC=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 NLTGIMKNKKMQPE-UHFFFAOYSA-N 0.000 description 1
• IJFUTQNLVKKPAV-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-pyrimidin-2-ylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2N=CC=CN=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 IJFUTQNLVKKPAV-UHFFFAOYSA-N 0.000 description 1
• XPCSVKMLDOUARP-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-pyrimidin-4-ylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C=2N=CN=CC=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 XPCSVKMLDOUARP-UHFFFAOYSA-N 0.000 description 1
• QLVUBIIDSKNVLZ-UHFFFAOYSA-N 1-[2-(4-chloro-3-fluorophenoxy)-5-fluorophenyl]-n-methylmethanamine Chemical compound CNCC1=CC(F)=CC=C1OC1=CC=C(Cl)C(F)=C1 QLVUBIIDSKNVLZ-UHFFFAOYSA-N 0.000 description 1
• SKSRGBRYENNADJ-UHFFFAOYSA-N 1-[2-(4-chlorophenoxy)-4,5-dimethylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C)=C(C)C=C1OC1=CC=C(Cl)C=C1 SKSRGBRYENNADJ-UHFFFAOYSA-N 0.000 description 1
• RBBPLEJTJYWGTE-UHFFFAOYSA-N 1-[2-(4-chlorophenoxy)-5-(1,2,4-triazol-4-yl)phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC(N2C=NN=C2)=CC=C1OC1=CC=C(Cl)C=C1 RBBPLEJTJYWGTE-UHFFFAOYSA-N 0.000 description 1
• MJXYTTAAIBVYCB-UHFFFAOYSA-N 1-[2-(4-chlorophenoxy)-5-(1-methylpyrrol-3-yl)phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC(C2=CN(C)C=C2)=CC=C1OC1=CC=C(Cl)C=C1 MJXYTTAAIBVYCB-UHFFFAOYSA-N 0.000 description 1
• IFULASKOIFNZJK-UHFFFAOYSA-N 1-[2-(4-chlorophenoxy)-5-(1-methyltetrazol-5-yl)phenyl]-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC(C=2N(N=NN=2)C)=CC=C1OC1=CC=C(Cl)C=C1 IFULASKOIFNZJK-UHFFFAOYSA-N 0.000 description 1
• RJUGAADERBRBOK-UHFFFAOYSA-N 1-[2-(4-chlorophenoxy)-5-(3,5-dimethyl-1,2,4-triazol-1-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(N2C(=NC(C)=N2)C)=CC=C1OC1=CC=C(Cl)C=C1 RJUGAADERBRBOK-UHFFFAOYSA-N 0.000 description 1
• LCRBMOQQJGVBOI-UHFFFAOYSA-N 1-[2-(4-chlorophenoxy)-5-propan-2-ylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C(C)C)=CC=C1OC1=CC=C(Cl)C=C1 LCRBMOQQJGVBOI-UHFFFAOYSA-N 0.000 description 1
• RQDLNRGGJROPPR-UHFFFAOYSA-N 1-[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]-3-methyl-1,3-diazinan-2-one Chemical compound CNCC1=CC(N2C(N(C)CCC2)=O)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 RQDLNRGGJROPPR-UHFFFAOYSA-N 0.000 description 1
• CCSCGUWEJSYZNZ-UHFFFAOYSA-N 1-[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]-3-methylimidazolidin-2-one Chemical compound CNCC1=CC(N2C(N(C)CC2)=O)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 CCSCGUWEJSYZNZ-UHFFFAOYSA-N 0.000 description 1
• CBFOMONXEQWNRB-UHFFFAOYSA-N 1-[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]piperidin-2-one Chemical compound CNCC1=CC(N2C(CCCC2)=O)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 CBFOMONXEQWNRB-UHFFFAOYSA-N 0.000 description 1
• WJYRLEWZANLZLM-UHFFFAOYSA-N 1-[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]pyrrolidin-2-one Chemical compound CNCC1=CC(N2C(CCC2)=O)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 WJYRLEWZANLZLM-UHFFFAOYSA-N 0.000 description 1
• QGLOKMBXFYKGID-UHFFFAOYSA-N 1-[4-(3,4-dichlorophenoxy)-3-[1-(methylamino)ethyl]phenyl]pyrrolidin-2-one Chemical compound CNC(C)C1=CC(N2C(CCC2)=O)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 QGLOKMBXFYKGID-UHFFFAOYSA-N 0.000 description 1
• XVMVPJRUNSOPIM-UHFFFAOYSA-N 1-[4-chloro-2-(3,4-dichlorophenoxy)-5-methylsulfonylphenyl]-n-methylmethanamine Chemical compound CNCC1=CC(S(C)(=O)=O)=C(Cl)C=C1OC1=CC=C(Cl)C(Cl)=C1 XVMVPJRUNSOPIM-UHFFFAOYSA-N 0.000 description 1
• NAEMAYGHANEAJP-UHFFFAOYSA-N 1-[4-chloro-2-(4-chlorophenoxy)-5-fluorophenyl]-n-methylmethanamine Chemical compound CNCC1=CC(F)=C(Cl)C=C1OC1=CC=C(Cl)C=C1 NAEMAYGHANEAJP-UHFFFAOYSA-N 0.000 description 1
• FJBCXFCOHTUVAN-UHFFFAOYSA-N 1-[5-chloro-2-(3,4-dichlorophenoxy)phenyl]-n-methylpropan-1-amine Chemical compound CCC(NC)C1=CC(Cl)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 FJBCXFCOHTUVAN-UHFFFAOYSA-N 0.000 description 1
• WIRTYVYQEXTSIB-UHFFFAOYSA-N 1-[5-fluoro-2-(4-fluoro-3-methoxyphenoxy)phenyl]-n,n-dimethylmethanamine Chemical compound C1=C(F)C(OC)=CC(OC=2C(=CC(F)=CC=2)CN(C)C)=C1 WIRTYVYQEXTSIB-UHFFFAOYSA-N 0.000 description 1
• PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 description 1
• KPFYMIPQCXAYKS-UHFFFAOYSA-N 1-methyl-3-[3-(methylaminomethyl)-4-naphthalen-2-yloxyphenyl]-1,3-diazinan-2-one Chemical compound C=1C=C(OC=2C=C3C=CC=CC3=CC=2)C(CNC)=CC=1N1CCCN(C)C1=O KPFYMIPQCXAYKS-UHFFFAOYSA-N 0.000 description 1
• JGPJINZMHOSMII-UHFFFAOYSA-N 1-methyl-3-[3-(methylaminomethyl)-4-naphthalen-2-yloxyphenyl]imidazolidin-2-one Chemical compound C=1C=C(OC=2C=C3C=CC=CC3=CC=2)C(CNC)=CC=1N1CCN(C)C1=O JGPJINZMHOSMII-UHFFFAOYSA-N 0.000 description 1
• BOMHEGKEVBTRBL-UHFFFAOYSA-N 1-methyl-3-[3-(methylaminomethyl)-4-naphthalen-2-yloxyphenyl]imidazolidine-2,4-dione Chemical compound C=1C=C(OC=2C=C3C=CC=CC3=CC=2)C(CNC)=CC=1N1C(=O)CN(C)C1=O BOMHEGKEVBTRBL-UHFFFAOYSA-N 0.000 description 1
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
• SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
• XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
• PTHWEAVZUFLNTB-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenoxy)-5-fluorophenyl]-1,2-dimethylpiperidine Chemical compound CN1CCCCC1(C)C1=CC(F)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 PTHWEAVZUFLNTB-UHFFFAOYSA-N 0.000 description 1
• PKDAKELWMBRZFQ-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenoxy)-5-fluorophenyl]-1,5-dimethylpyrrolidine Chemical compound CN1C(C)CCC1C1=CC(F)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 PKDAKELWMBRZFQ-UHFFFAOYSA-N 0.000 description 1
• OXYPLWPQQDDYFW-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenoxy)-5-fluorophenyl]-1-methylpiperidine Chemical compound CN1CCCCC1C1=CC(F)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 OXYPLWPQQDDYFW-UHFFFAOYSA-N 0.000 description 1
• ZKWNWOMNZUTWAF-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenoxy)-5-fluorophenyl]piperidine Chemical compound C1CCCNC1C1=CC(F)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 ZKWNWOMNZUTWAF-UHFFFAOYSA-N 0.000 description 1
• SJTQXWBXLFJXNA-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenoxy)-5-methylsulfanylphenyl]-n-methylpropan-2-amine Chemical compound CNC(C)(C)C1=CC(SC)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 SJTQXWBXLFJXNA-UHFFFAOYSA-N 0.000 description 1
• WOYXTNYWFYWXFO-UHFFFAOYSA-N 2-[3-(trifluoromethyl)anilino]pyridine-3-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CN=C1NC1=CC=CC(C(F)(F)F)=C1 WOYXTNYWFYWXFO-UHFFFAOYSA-N 0.000 description 1
• 125000001698 2H-pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
• ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
• CFCFNOBVEQYCRG-UHFFFAOYSA-N 3-[2-(3,4-dichlorophenoxy)-5-fluorophenyl]-4-methylmorpholine Chemical compound CN1CCOCC1C1=CC(F)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 CFCFNOBVEQYCRG-UHFFFAOYSA-N 0.000 description 1
• LFTUZGHRTOFCPA-UHFFFAOYSA-N 3-[2-(3,4-dichlorophenoxy)-5-fluorophenyl]-4-methylthiomorpholine Chemical compound CN1CCSCC1C1=CC(F)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 LFTUZGHRTOFCPA-UHFFFAOYSA-N 0.000 description 1
• VCWUFWSDFBJEQI-UHFFFAOYSA-N 3-[3-(methylaminomethyl)-4-naphthalen-2-yloxyphenyl]-1,3-oxazolidin-2-one Chemical compound C=1C=C(OC=2C=C3C=CC=CC3=CC=2)C(CNC)=CC=1N1CCOC1=O VCWUFWSDFBJEQI-UHFFFAOYSA-N 0.000 description 1
• ZFRYGKBVPCZLJN-UHFFFAOYSA-N 3-[3-(methylaminomethyl)-4-naphthalen-2-yloxyphenyl]-1,3-oxazolidine-2,4-dione Chemical compound C=1C=C(OC=2C=C3C=CC=CC3=CC=2)C(CNC)=CC=1N1C(=O)COC1=O ZFRYGKBVPCZLJN-UHFFFAOYSA-N 0.000 description 1
• CRLPHIQRZBJONV-UHFFFAOYSA-N 3-[3-(methylaminomethyl)-4-naphthalen-2-yloxyphenyl]-1,3-thiazolidin-2-one Chemical compound C=1C=C(OC=2C=C3C=CC=CC3=CC=2)C(CNC)=CC=1N1CCSC1=O CRLPHIQRZBJONV-UHFFFAOYSA-N 0.000 description 1
• BXMDAAMKQKMCDJ-UHFFFAOYSA-N 3-[3-(methylaminomethyl)-4-naphthalen-2-yloxyphenyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=C(OC=2C=C3C=CC=CC3=CC=2)C(CNC)=CC=1N1C(=O)CSC1=O BXMDAAMKQKMCDJ-UHFFFAOYSA-N 0.000 description 1
• UCPFVAVDWQJACV-UHFFFAOYSA-N 3-[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]-1,3-oxazolidin-2-one Chemical compound CNCC1=CC(N2C(OCC2)=O)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 UCPFVAVDWQJACV-UHFFFAOYSA-N 0.000 description 1
• QZHYCJAXBITRRZ-UHFFFAOYSA-N 3-[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]-1,3-thiazolidin-2-one Chemical compound CNCC1=CC(N2C(SCC2)=O)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 QZHYCJAXBITRRZ-UHFFFAOYSA-N 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
• NVXGKVLUJXXCLR-UHFFFAOYSA-N 4-(3,4-dichlorophenoxy)-3-[(dimethylamino)methyl]-n,n-dimethylaniline Chemical compound CN(C)CC1=CC(N(C)C)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 NVXGKVLUJXXCLR-UHFFFAOYSA-N 0.000 description 1
• YZHISSCBAUQDOP-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)-3-(1-methylpyrrolidin-2-yl)phenyl]-2-methylpyrimidine Chemical compound CN1CCCC1C1=CC(C=2N=C(C)N=CC=2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 YZHISSCBAUQDOP-UHFFFAOYSA-N 0.000 description 1
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
• 125000001826 4H-pyranyl group Chemical group O1C(=CCC=C1)* 0.000 description 1
• FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
• BLYMJBIZMIGWFK-UHFFFAOYSA-N 7-(dipropylamino)-5,6,7,8-tetrahydronaphthalen-2-ol Chemical compound C1=C(O)C=C2CC(N(CCC)CCC)CCC2=C1 BLYMJBIZMIGWFK-UHFFFAOYSA-N 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• 235000019489 Almond oil Nutrition 0.000 description 1
• 208000024827 Alzheimer disease Diseases 0.000 description 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
• 208000000103 Anorexia Nervosa Diseases 0.000 description 1
• 241000416162 Astragalus gummifer Species 0.000 description 1
• 241000283690 Bos taurus Species 0.000 description 1
• 208000032841 Bulimia Diseases 0.000 description 1
• 206010006550 Bulimia nervosa Diseases 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• 241000282472 Canis lupus familiaris Species 0.000 description 1
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
• OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
• 206010008479 Chest Pain Diseases 0.000 description 1
• 229920002261 Corn starch Polymers 0.000 description 1
• 241000699802 Cricetulus griseus Species 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
• DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-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
• RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
• HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 1
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
• 229920002307 Dextran Polymers 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
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
• 108010044266 Dopamine Plasma Membrane Transport Proteins Proteins 0.000 description 1
• 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
• 208000027534 Emotional disease Diseases 0.000 description 1
• 241000588724 Escherichia coli Species 0.000 description 1
• 241000282326 Felis catus Species 0.000 description 1
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
• 239000004471 Glycine Substances 0.000 description 1
• 235000010469 Glycine max Nutrition 0.000 description 1
• 241000238631 Hexapoda Species 0.000 description 1
• 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
• 206010020710 Hyperphagia Diseases 0.000 description 1
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
• WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
• LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
• ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
• 229930182816 L-glutamine Natural products 0.000 description 1
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 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
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
• 238000005481 NMR spectroscopy Methods 0.000 description 1
• 229910002651 NO3 Inorganic materials 0.000 description 1
• 206010028813 Nausea Diseases 0.000 description 1
• 206010029333 Neurosis Diseases 0.000 description 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
• 102000008092 Norepinephrine Plasma Membrane Transport Proteins Human genes 0.000 description 1
• 108010049586 Norepinephrine Plasma Membrane Transport Proteins Proteins 0.000 description 1
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
• WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
• 206010033557 Palpitations Diseases 0.000 description 1
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
• 239000004743 Polypropylene Substances 0.000 description 1
• 229920001214 Polysorbate 60 Polymers 0.000 description 1
• 206010062519 Poor quality sleep Diseases 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
• 239000007868 Raney catalyst Substances 0.000 description 1
• NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
• 229910000564 Raney nickel Inorganic materials 0.000 description 1
• PPTYJKAXVCCBDU-UHFFFAOYSA-N Rohypnol Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1F PPTYJKAXVCCBDU-UHFFFAOYSA-N 0.000 description 1
• XDXHAEQXIBQUEZ-UHFFFAOYSA-N Ropinirole hydrochloride Chemical compound Cl.CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2 XDXHAEQXIBQUEZ-UHFFFAOYSA-N 0.000 description 1
• 235000019485 Safflower oil Nutrition 0.000 description 1
• 101710150104 Sensory rhodopsin-1 Proteins 0.000 description 1
• 244000000231 Sesamum indicum Species 0.000 description 1
• 229920001800 Shellac Polymers 0.000 description 1
• DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
• 101710114615 Sodium-dependent dopamine transporter Proteins 0.000 description 1
• 244000061456 Solanum tuberosum Species 0.000 description 1
• 235000002595 Solanum tuberosum Nutrition 0.000 description 1
• 235000021355 Stearic acid Nutrition 0.000 description 1
• 208000013200 Stress disease Diseases 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• 239000004809 Teflon Substances 0.000 description 1
• 229920006362 Teflon® Polymers 0.000 description 1
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
• LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• 208000031674 Traumatic Acute Stress disease Diseases 0.000 description 1
• 229940123445 Tricyclic antidepressant Drugs 0.000 description 1
• 201000004810 Vascular dementia Diseases 0.000 description 1
• 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 1
• 206010052428 Wound Diseases 0.000 description 1
• 208000027418 Wounds and injury Diseases 0.000 description 1
• 240000008042 Zea mays Species 0.000 description 1
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
• NJVHJTQSGGRHGP-UHFFFAOYSA-K [Li].[Al+3].[Cl-].[Cl-].[Cl-] Chemical compound [Li].[Al+3].[Cl-].[Cl-].[Cl-] NJVHJTQSGGRHGP-UHFFFAOYSA-K 0.000 description 1
• 150000001241 acetals Chemical class 0.000 description 1
• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
• 125000002252 acyl group Chemical group 0.000 description 1
• 208000012826 adjustment disease Diseases 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 229940072056 alginate Drugs 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
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
• 239000008168 almond oil Substances 0.000 description 1
• AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [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
• 238000004458 analytical method Methods 0.000 description 1
• 201000002426 animal phobia Diseases 0.000 description 1
• 150000001450 anions Chemical class 0.000 description 1
• 208000022531 anorexia Diseases 0.000 description 1
• 239000005557 antagonist Substances 0.000 description 1
• 239000012736 aqueous medium Substances 0.000 description 1
• 239000003125 aqueous solvent Substances 0.000 description 1
• 208000025748 atypical depressive disease Diseases 0.000 description 1
• VJBCNMFKFZIXHC-UHFFFAOYSA-N azanium;2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)quinoline-3-carboxylate Chemical compound N.N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O VJBCNMFKFZIXHC-UHFFFAOYSA-N 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
• 230000003542 behavioural effect Effects 0.000 description 1
• RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 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
• 229940077388 benzenesulfonate Drugs 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=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
• 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
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
• 239000011230 binding agent Substances 0.000 description 1
• 208000028683 bipolar I disease Diseases 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
• 230000037396 body weight Effects 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 210000004556 brain Anatomy 0.000 description 1
• 125000001246 bromo group Chemical group Br* 0.000 description 1
• SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 description 1
• 229960001058 bupropion Drugs 0.000 description 1
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
• 229960001948 caffeine Drugs 0.000 description 1
• VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 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
• 229910000389 calcium phosphate Inorganic materials 0.000 description 1
• 235000011089 carbon dioxide Nutrition 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• 239000001768 carboxy methyl cellulose Substances 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
• 229920002301 cellulose acetate Polymers 0.000 description 1
• 210000003169 central nervous system Anatomy 0.000 description 1
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
• 230000027288 circadian rhythm Effects 0.000 description 1
• 238000000576 coating method Methods 0.000 description 1
• 239000003240 coconut oil Substances 0.000 description 1
• 235000019864 coconut oil Nutrition 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 238000004891 communication Methods 0.000 description 1
• 239000012141 concentrate Substances 0.000 description 1
• 235000009508 confectionery Nutrition 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 230000036461 convulsion Effects 0.000 description 1
• 235000005822 corn Nutrition 0.000 description 1
• 235000005687 corn oil Nutrition 0.000 description 1
• 239000002285 corn oil Substances 0.000 description 1
• 239000008120 corn starch Substances 0.000 description 1
• 206010061428 decreased appetite Diseases 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 230000003111 delayed effect Effects 0.000 description 1
• 230000003001 depressive effect Effects 0.000 description 1
• 229960003914 desipramine Drugs 0.000 description 1
• 230000001627 detrimental effect Effects 0.000 description 1
• 229910052805 deuterium Inorganic materials 0.000 description 1
• 238000011161 development Methods 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
• 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
• 229940038472 dicalcium phosphate Drugs 0.000 description 1
• GRTGGSXWHGKRSB-UHFFFAOYSA-N dichloromethyl methyl ether Chemical compound COC(Cl)Cl GRTGGSXWHGKRSB-UHFFFAOYSA-N 0.000 description 1
• GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
• 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
• 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
• 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 description 1
• 125000000532 dioxanyl group Chemical group 0.000 description 1
• LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• 208000002173 dizziness Diseases 0.000 description 1
• 239000003136 dopamine receptor stimulating agent Substances 0.000 description 1
• 229940005501 dopaminergic agent Drugs 0.000 description 1
• 206010013663 drug dependence Diseases 0.000 description 1
• 210000001198 duodenum Anatomy 0.000 description 1
• 239000000975 dye Substances 0.000 description 1
• 239000008157 edible vegetable oil Substances 0.000 description 1
• 239000002895 emetic Substances 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 230000001804 emulsifying effect Effects 0.000 description 1
• 230000007368 endocrine function Effects 0.000 description 1
• 239000002702 enteric coating Substances 0.000 description 1
• 230000032050 esterification Effects 0.000 description 1
• 238000005886 esterification reaction Methods 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• 150000002170 ethers Chemical class 0.000 description 1
• 230000001605 fetal effect Effects 0.000 description 1
• 239000012467 final product Substances 0.000 description 1
• 239000012054 flavored emulsion Substances 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 235000020375 flavoured syrup Nutrition 0.000 description 1
• 230000010006 flight Effects 0.000 description 1
• UQSQSQZYBQSBJZ-UHFFFAOYSA-M fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 235000003599 food sweetener Nutrition 0.000 description 1
• 239000013022 formulation composition Substances 0.000 description 1
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
• 230000022244 formylation Effects 0.000 description 1
• 238000006170 formylation reaction Methods 0.000 description 1
• 125000000524 functional group Chemical group 0.000 description 1
• 125000003838 furazanyl group Chemical group 0.000 description 1
• 239000007789 gas Substances 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• 229940050410 gluconate Drugs 0.000 description 1
• 239000008187 granular material Substances 0.000 description 1
• 150000004820 halides Chemical class 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 210000001320 hippocampus Anatomy 0.000 description 1
• 239000008240 homogeneous mixture Substances 0.000 description 1
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
• 238000005984 hydrogenation reaction Methods 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
• 125000002632 imidazolidinyl group Chemical group 0.000 description 1
• 125000002636 imidazolinyl group Chemical group 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 238000011065 in-situ storage Methods 0.000 description 1
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 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
• 239000011261 inert gas Substances 0.000 description 1
• 230000002401 inhibitory effect Effects 0.000 description 1
• 230000005764 inhibitory process Effects 0.000 description 1
• 208000014674 injury Diseases 0.000 description 1
• 229940028435 intralipid Drugs 0.000 description 1
• 238000010253 intravenous injection Methods 0.000 description 1
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
• 125000002346 iodo group Chemical group I* 0.000 description 1
• 230000007794 irritation Effects 0.000 description 1
• FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 1
• 125000005956 isoquinolyl group Chemical group 0.000 description 1
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
• 125000000842 isoxazolyl group Chemical group 0.000 description 1
• 239000003446 ligand Substances 0.000 description 1
• 239000002960 lipid emulsion Substances 0.000 description 1
• 229910000103 lithium hydride Inorganic materials 0.000 description 1
• 230000007774 longterm Effects 0.000 description 1
• 239000007937 lozenge Substances 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
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 240000004308 marijuana Species 0.000 description 1
• 238000005259 measurement Methods 0.000 description 1
• 230000007246 mechanism Effects 0.000 description 1
• 229960003194 meglumine Drugs 0.000 description 1
• 201000003995 melancholia Diseases 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 235000010981 methylcellulose Nutrition 0.000 description 1
• 239000008108 microcrystalline cellulose Substances 0.000 description 1
• 229940016286 microcrystalline cellulose Drugs 0.000 description 1
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 229940101972 mirapex Drugs 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
• 239000002808 molecular sieve Substances 0.000 description 1
• 239000002899 monoamine oxidase inhibitor Substances 0.000 description 1
• 230000036651 mood Effects 0.000 description 1
• 230000001095 motoneuron effect Effects 0.000 description 1
• YDSVAKPJAOSZJA-UHFFFAOYSA-N n-methyl-4,5,6,7-tetrahydro-1,3-benzothiazol-6-amine Chemical compound C1C(NC)CCC2=C1SC=N2 YDSVAKPJAOSZJA-UHFFFAOYSA-N 0.000 description 1
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
• 229920001206 natural gum Polymers 0.000 description 1
• 230000008693 nausea Effects 0.000 description 1
• 210000001577 neostriatum Anatomy 0.000 description 1
• 101150006061 neur gene Proteins 0.000 description 1
• 208000025319 neurotic depression Diseases 0.000 description 1
• 230000019818 neurotransmitter uptake Effects 0.000 description 1
• 230000007935 neutral effect Effects 0.000 description 1
• KFBKRCXOTTUAFS-UHFFFAOYSA-N nickel;triphenylphosphane Chemical compound [Ni].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 KFBKRCXOTTUAFS-UHFFFAOYSA-N 0.000 description 1
• 125000002560 nitrile group Chemical group 0.000 description 1
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
• 229960001073 nomifensine Drugs 0.000 description 1
• XXPANQJNYNUNES-UHFFFAOYSA-N nomifensine Chemical compound C12=CC=CC(N)=C2CN(C)CC1C1=CC=CC=C1 XXPANQJNYNUNES-UHFFFAOYSA-N 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• 229940005483 opioid analgesics Drugs 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 239000008203 oral pharmaceutical composition Substances 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 125000002524 organometallic group Chemical group 0.000 description 1
• 210000001672 ovary Anatomy 0.000 description 1
• 125000000160 oxazolidinyl group Chemical group 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 125000003566 oxetanyl group Chemical group 0.000 description 1
• 125000000466 oxiranyl group Chemical group 0.000 description 1
• MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 239000004031 partial agonist Substances 0.000 description 1
• 230000036961 partial effect Effects 0.000 description 1
• 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
• 239000008024 pharmaceutical diluent Substances 0.000 description 1
• 239000002953 phosphate buffered saline Substances 0.000 description 1
• 229910052698 phosphorus Inorganic materials 0.000 description 1
• 239000011574 phosphorus Substances 0.000 description 1
• FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 125000003386 piperidinyl group Chemical group 0.000 description 1
• 125000003367 polycyclic group Chemical group 0.000 description 1
• 229920001223 polyethylene glycol Polymers 0.000 description 1
• 229920001155 polypropylene Polymers 0.000 description 1
• 208000028173 post-traumatic stress disease Diseases 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 229910000027 potassium carbonate Inorganic materials 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 229960002652 pramipexole dihydrochloride Drugs 0.000 description 1
• 230000002035 prolonged effect Effects 0.000 description 1
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
• 229940001470 psychoactive drug Drugs 0.000 description 1
• 239000004089 psychotropic agent Substances 0.000 description 1
• 230000000506 psychotropic effect Effects 0.000 description 1
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
• 229950010131 puromycin Drugs 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
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• 125000005493 quinolyl group Chemical group 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
• 239000002516 radical scavenger Substances 0.000 description 1
• 239000002287 radioligand Substances 0.000 description 1
• 102000005962 receptors Human genes 0.000 description 1
• 108020003175 receptors Proteins 0.000 description 1
• 230000000306 recurrent effect Effects 0.000 description 1
• 238000006268 reductive amination reaction Methods 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 238000011160 research Methods 0.000 description 1
• 230000000241 respiratory effect Effects 0.000 description 1
• 238000006798 ring closing metathesis reaction Methods 0.000 description 1
• 229960002349 ropinirole hydrochloride Drugs 0.000 description 1
• 235000005713 safflower oil Nutrition 0.000 description 1
• 239000003813 safflower oil Substances 0.000 description 1
• 208000012672 seasonal affective disease Diseases 0.000 description 1
• 230000036280 sedation Effects 0.000 description 1
• 230000000697 serotonin reuptake Effects 0.000 description 1
• 239000003772 serotonin uptake inhibitor Substances 0.000 description 1
• 229960002073 sertraline Drugs 0.000 description 1
• VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 1
• 239000004208 shellac Substances 0.000 description 1
• ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
• 229940113147 shellac Drugs 0.000 description 1
• 235000013874 shellac Nutrition 0.000 description 1
• 150000004760 silicates Chemical class 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
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
• 229920001027 sodium carboxymethylcellulose Polymers 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
• 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
• 239000008279 sol Substances 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 239000008347 soybean phospholipid Substances 0.000 description 1
• 241000894007 species Species 0.000 description 1
• 230000009870 specific binding Effects 0.000 description 1
• 125000003003 spiro group Chemical group 0.000 description 1
• 238000013222 sprague-dawley male rat Methods 0.000 description 1
• 238000012453 sprague-dawley rat model Methods 0.000 description 1
• 238000010561 standard procedure Methods 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 210000002784 stomach Anatomy 0.000 description 1
• 238000003860 storage Methods 0.000 description 1
• 238000010254 subcutaneous injection Methods 0.000 description 1
• 239000007929 subcutaneous injection Substances 0.000 description 1
• 208000011117 substance-related disease Diseases 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• 239000000758 substrate Substances 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
• 150000003457 sulfones Chemical class 0.000 description 1
• 230000035900 sweating Effects 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 230000002195 synergetic effect Effects 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 230000009885 systemic effect Effects 0.000 description 1
• 235000012222 talc Nutrition 0.000 description 1
• 229940095064 tartrate Drugs 0.000 description 1
• VQMNWIMYFHHFMC-UHFFFAOYSA-N tert-butyl 4-hydroxyindole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC(C)(C)C)C=CC2=C1O VQMNWIMYFHHFMC-UHFFFAOYSA-N 0.000 description 1
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
• 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• 125000001113 thiadiazolyl 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
• 125000005503 thioxanyl group Chemical group 0.000 description 1
• 238000003354 tissue distribution assay Methods 0.000 description 1
• 235000010487 tragacanth Nutrition 0.000 description 1
• 239000000196 tragacanth Substances 0.000 description 1
• 229940116362 tragacanth Drugs 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• 125000001425 triazolyl group Chemical group 0.000 description 1
• 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
• 238000010200 validation analysis Methods 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 238000005303 weighing Methods 0.000 description 1
• 239000004563 wettable powder Substances 0.000 description 1
• 239000002023 wood Substances 0.000 description 1