JP2002371059A

JP2002371059A - メラニン凝集ホルモン拮抗剤

メラニン凝集ホルモン拮抗剤

Info

Publication number: JP2002371059A
Authority: JP; Japan
Prior art keywords: substituent; group; ring; nitrogen; compound
Prior art date: 2000-05-16
Legal status : Withdrawn

Application number

JP2001145691A

Other languages

English (en)

Japanese (ja)

Other versions

JP2002371059A5 (enExample

Inventor

Yuji Ishihara

雄二石原

Atsushi Terauchi

淳寺内

Nobuhiro Suzuki

伸宏鈴木

Shiro Takekawa

志郎竹河

Kazuyoshi Aso

和義麻生

Current Assignee

Takeda Pharmaceutical Co Ltd

Original Assignee

Takeda Chemical Industries Ltd

Priority date

2000-05-16

Filing date

2001-05-15

Publication date

2002-12-26

2001-05-15 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

2001-05-15 Priority to JP2001145691A priority Critical patent/JP2002371059A/ja

2002-12-26 Publication of JP2002371059A publication Critical patent/JP2002371059A/ja

2008-06-26 Publication of JP2002371059A5 publication Critical patent/JP2002371059A5/ja

Status Withdrawn legal-status Critical Current

Links

239000003667 hormone antagonist Substances 0.000 title claims abstract description 10
150000001875 compounds Chemical class 0.000 claims abstract description 508
125000001424 substituent group Chemical group 0.000 claims abstract description 380
150000003839 salts Chemical class 0.000 claims abstract description 71
125000005843 halogen group Chemical group 0.000 claims abstract description 58
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 56
125000004122 cyclic group Chemical group 0.000 claims abstract description 46
125000004429 atom Chemical group 0.000 claims abstract description 39
125000006850 spacer group Chemical group 0.000 claims abstract description 34
239000003795 chemical substances by application Substances 0.000 claims abstract description 29
208000008589 Obesity Diseases 0.000 claims abstract description 28
235000020824 obesity Nutrition 0.000 claims abstract description 28
125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 16
-1 biphenylyl Chemical group 0.000 claims description 508
125000000217 alkyl group Chemical group 0.000 claims description 160
125000000623 heterocyclic group Chemical group 0.000 claims description 73
229910052757 nitrogen Inorganic materials 0.000 claims description 73
125000003118 aryl group Chemical group 0.000 claims description 71
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 71
238000000034 method Methods 0.000 claims description 70
125000004433 nitrogen atom Chemical group N* 0.000 claims description 58
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 53
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 45
101800002739 Melanin-concentrating hormone Proteins 0.000 claims description 44
239000003814 drug Substances 0.000 claims description 36
238000004519 manufacturing process Methods 0.000 claims description 30
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 26
239000008194 pharmaceutical composition Substances 0.000 claims description 26
125000002950 monocyclic group Chemical group 0.000 claims description 25
229940079593 drug Drugs 0.000 claims description 22
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
125000003277 amino group Chemical group 0.000 claims description 14
201000010099 disease Diseases 0.000 claims description 14
229940002612 prodrug Drugs 0.000 claims description 14
239000000651 prodrug Substances 0.000 claims description 14
ORRDHOMWDPJSNL-UHFFFAOYSA-N melanin concentrating hormone Chemical compound N1C(=O)C(C(C)C)NC(=O)C(CCCNC(N)=N)NC(=O)CNC(=O)C(C(C)C)NC(=O)C(CCSC)NC(=O)C(NC(=O)C(CCCNC(N)=N)NC(=O)C(NC(=O)C(NC(=O)C(N)CC(O)=O)C(C)O)CCSC)CSSCC(C(=O)NC(CC=2C3=CC=CC=C3NC=2)C(=O)NC(CCC(O)=O)C(=O)NC(C(C)C)C(O)=O)NC(=O)C2CCCN2C(=O)C(CCCNC(N)=N)NC(=O)C1CC1=CC=C(O)C=C1 ORRDHOMWDPJSNL-UHFFFAOYSA-N 0.000 claims description 13
102000047659 melanin-concentrating hormone Human genes 0.000 claims description 13
229940124597 therapeutic agent Drugs 0.000 claims description 12
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 9
125000006618 5- to 10-membered aromatic heterocyclic group Chemical group 0.000 claims description 8
241000124008 Mammalia Species 0.000 claims description 8
230000000069 prophylactic effect Effects 0.000 claims description 8
206010012601 diabetes mellitus Diseases 0.000 claims description 7
125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 claims description 6
125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 5
206010003210 Arteriosclerosis Diseases 0.000 claims description 5
208000011775 arteriosclerosis disease Diseases 0.000 claims description 5
206010020772 Hypertension Diseases 0.000 claims description 4
230000001887 anti-feedant effect Effects 0.000 claims description 4
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 4
125000002015 acyclic group Chemical group 0.000 claims description 3
SPCXCXWTBGVFJF-UHFFFAOYSA-N 4,5-dihydro-3h-azepine Chemical compound C1CC=CN=CC1 SPCXCXWTBGVFJF-UHFFFAOYSA-N 0.000 claims 1
125000005647 linker group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 186
239000002904 solvent Substances 0.000 description 170
238000005160 1H NMR spectroscopy Methods 0.000 description 118
239000000843 powder Substances 0.000 description 109
239000000243 solution Substances 0.000 description 77
238000006243 chemical reaction Methods 0.000 description 71
239000000203 mixture Substances 0.000 description 70
230000008018 melting Effects 0.000 description 67
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 66
238000002425 crystallisation Methods 0.000 description 66
230000008025 crystallization Effects 0.000 description 66
238000002844 melting Methods 0.000 description 66
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 63
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 62
235000002639 sodium chloride Nutrition 0.000 description 59
125000003545 alkoxy group Chemical group 0.000 description 58
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
230000002829 reductive effect Effects 0.000 description 49
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 45
125000002887 hydroxy group Chemical group [H]O* 0.000 description 43
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
229910052739 hydrogen Inorganic materials 0.000 description 40
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 34
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 33
102400001132 Melanin-concentrating hormone Human genes 0.000 description 31
239000002585 base Substances 0.000 description 31
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 30
239000000460 chlorine Substances 0.000 description 30
OYJXTOVLKZDGFK-UHFFFAOYSA-N ethanol;2-propan-2-yloxypropane Chemical compound CCO.CC(C)OC(C)C OYJXTOVLKZDGFK-UHFFFAOYSA-N 0.000 description 30
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 30
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 28
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 28
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
229910052801 chlorine Inorganic materials 0.000 description 28
150000002430 hydrocarbons Chemical group 0.000 description 28
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 28
238000005481 NMR spectroscopy Methods 0.000 description 27
238000000921 elemental analysis Methods 0.000 description 26
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 25
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
125000003710 aryl alkyl group Chemical group 0.000 description 25
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 25
229910052794 bromium Inorganic materials 0.000 description 25
239000012458 free base Substances 0.000 description 25
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 23
239000005557 antagonist Substances 0.000 description 23
239000011737 fluorine Substances 0.000 description 23
229910052731 fluorine Inorganic materials 0.000 description 23
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
239000001257 hydrogen Substances 0.000 description 21
235000011121 sodium hydroxide Nutrition 0.000 description 21
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 19
239000013078 crystal Substances 0.000 description 19
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 19
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 18
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
238000006482 condensation reaction Methods 0.000 description 18
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 17
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 17
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 16
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 16
239000003921 oil Substances 0.000 description 16
235000019198 oils Nutrition 0.000 description 16
125000004430 oxygen atom Chemical group O* 0.000 description 16
238000006722 reduction reaction Methods 0.000 description 16
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 15
125000002252 acyl group Chemical group 0.000 description 15
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 15
239000012442 inert solvent Substances 0.000 description 15
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
238000004440 column chromatography Methods 0.000 description 14
238000001816 cooling Methods 0.000 description 14
125000005842 heteroatom Chemical group 0.000 description 14
230000003287 optical effect Effects 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
150000002367 halogens Chemical class 0.000 description 13
239000000126 substance Substances 0.000 description 13
229910052717 sulfur Inorganic materials 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
108020004414 DNA Proteins 0.000 description 12
101000581402 Homo sapiens Melanin-concentrating hormone receptor 1 Proteins 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
125000005431 alkyl carboxamide group Chemical group 0.000 description 12
150000001408 amides Chemical class 0.000 description 12
239000012267 brine Substances 0.000 description 12
239000002299 complementary DNA Substances 0.000 description 12
229910052736 halogen Inorganic materials 0.000 description 12
102000047277 human MCHR1 Human genes 0.000 description 12
229910000027 potassium carbonate Inorganic materials 0.000 description 12
235000011181 potassium carbonates Nutrition 0.000 description 12
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 11
239000002253 acid Substances 0.000 description 11
UYYVQUKNAJEDST-UHFFFAOYSA-N n-[2-(3,4-dihydro-2h-1,4-benzoxazin-6-yl)ethyl]-n-propylpropan-1-amine;hydrochloride Chemical compound Cl.O1CCNC2=CC(CCN(CCC)CCC)=CC=C21 UYYVQUKNAJEDST-UHFFFAOYSA-N 0.000 description 11
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 11
238000002360 preparation method Methods 0.000 description 11
238000010898 silica gel chromatography Methods 0.000 description 11
235000017557 sodium bicarbonate Nutrition 0.000 description 11
229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
238000003786 synthesis reaction Methods 0.000 description 11
125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 10
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 10
239000007864 aqueous solution Substances 0.000 description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 10
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
239000003054 catalyst Substances 0.000 description 10
125000004093 cyano group Chemical group *C#N 0.000 description 10
238000005886 esterification reaction Methods 0.000 description 10
238000001704 evaporation Methods 0.000 description 10
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 10
125000004043 oxo group Chemical group O=* 0.000 description 10
125000003386 piperidinyl group Chemical group 0.000 description 10
238000003756 stirring Methods 0.000 description 10
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
239000004215 Carbon black (E152) Substances 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
125000004423 acyloxy group Chemical group 0.000 description 9
125000000753 cycloalkyl group Chemical group 0.000 description 9
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 9
238000006297 dehydration reaction Methods 0.000 description 9
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 9
229930195733 hydrocarbon Natural products 0.000 description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
125000006239 protecting group Chemical group 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
230000035484 reaction time Effects 0.000 description 9
229920006395 saturated elastomer Polymers 0.000 description 9
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 description 8
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 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
102000004877 Insulin Human genes 0.000 description 8
108090001061 Insulin Proteins 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
229910052783 alkali metal Inorganic materials 0.000 description 8
125000004390 alkyl sulfonyl group Chemical group 0.000 description 8
125000005530 alkylenedioxy group Chemical group 0.000 description 8
239000003849 aromatic solvent Substances 0.000 description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 8
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 8
150000008282 halocarbons Chemical class 0.000 description 8
229940125396 insulin Drugs 0.000 description 8
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 8
150000002825 nitriles Chemical class 0.000 description 8
229910052760 oxygen Inorganic materials 0.000 description 8
239000001301 oxygen Substances 0.000 description 8
125000003367 polycyclic group Chemical group 0.000 description 8
125000005750 substituted cyclic group Chemical group 0.000 description 8
125000004434 sulfur atom Chemical group 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
ZBFKVMTXHJBNHZ-UHFFFAOYSA-N 4-oxo-4-[3-(2,2,2-trifluoroacetyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl]butanoic acid Chemical compound C1CN(C(=O)C(F)(F)F)CCC2=CC(C(=O)CCC(=O)O)=CC=C21 ZBFKVMTXHJBNHZ-UHFFFAOYSA-N 0.000 description 7
125000005914 C6-C14 aryloxy group Chemical group 0.000 description 7
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
229960000583 acetic acid Drugs 0.000 description 7
229910052784 alkaline earth metal Inorganic materials 0.000 description 7
238000007112 amidation reaction Methods 0.000 description 7
150000001413 amino acids Chemical class 0.000 description 7
125000005199 aryl carbonyloxy group Chemical group 0.000 description 7
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
239000004210 ether based solvent Substances 0.000 description 7
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 7
150000002431 hydrogen Chemical class 0.000 description 7
239000005453 ketone based solvent Substances 0.000 description 7
125000004193 piperazinyl group Chemical group 0.000 description 7
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 7
125000000719 pyrrolidinyl group Chemical group 0.000 description 7
229910000029 sodium carbonate Inorganic materials 0.000 description 7
235000017550 sodium carbonate Nutrition 0.000 description 7
150000003462 sulfoxides Chemical class 0.000 description 7
239000011593 sulfur Substances 0.000 description 7
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 6
LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 6
HQXKYBKBKFNTII-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-(2,3-dihydro-1h-isoindol-5-yl)butane-1,4-dione Chemical compound C1=CC(Cl)=CC=C1C1CCN(C(=O)CCC(=O)C=2C=C3CNCC3=CC=2)CC1 HQXKYBKBKFNTII-UHFFFAOYSA-N 0.000 description 6
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 6
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 description 6
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
150000001340 alkali metals Chemical class 0.000 description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 description 6
125000005115 alkyl carbamoyl group Chemical group 0.000 description 6
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 6
125000002102 aryl alkyloxo group Chemical group 0.000 description 6
125000005116 aryl carbamoyl group Chemical group 0.000 description 6
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 6
239000011630 iodine Substances 0.000 description 6
229910052740 iodine Inorganic materials 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 6
235000011118 potassium hydroxide Nutrition 0.000 description 6
125000004076 pyridyl group Chemical group 0.000 description 6
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
238000012216 screening Methods 0.000 description 6
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
QIXORTWTAVZFFR-UHFFFAOYSA-N 2,2,2-trifluoro-1-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)ethanone Chemical compound C1CN(C(=O)C(F)(F)F)CCC2=CC=CC=C21 QIXORTWTAVZFFR-UHFFFAOYSA-N 0.000 description 5
208000002249 Diabetes Complications Diseases 0.000 description 5
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
101000581407 Rattus norvegicus Melanin-concentrating hormone receptor 1 Proteins 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
125000004442 acylamino group Chemical group 0.000 description 5
125000005236 alkanoylamino group Chemical group 0.000 description 5
125000003342 alkenyl group Chemical group 0.000 description 5
235000001014 amino acid Nutrition 0.000 description 5
229940024606 amino acid Drugs 0.000 description 5
230000003042 antagnostic effect Effects 0.000 description 5
239000000883 anti-obesity agent Substances 0.000 description 5
239000002830 appetite depressant Substances 0.000 description 5
125000005018 aryl alkenyl group Chemical group 0.000 description 5
125000004391 aryl sulfonyl group Chemical group 0.000 description 5
150000001721 carbon Chemical group 0.000 description 5
238000005859 coupling reaction Methods 0.000 description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000003480 eluent Substances 0.000 description 5
230000032050 esterification Effects 0.000 description 5
150000002148 esters Chemical group 0.000 description 5
WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 5
125000000524 functional group Chemical group 0.000 description 5
230000014509 gene expression Effects 0.000 description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
229910052987 metal hydride Inorganic materials 0.000 description 5
150000004681 metal hydrides Chemical class 0.000 description 5
150000007524 organic acids Chemical class 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 5
229910000028 potassium bicarbonate Inorganic materials 0.000 description 5
239000011736 potassium bicarbonate Substances 0.000 description 5
235000015497 potassium bicarbonate Nutrition 0.000 description 5
229940086066 potassium hydrogencarbonate Drugs 0.000 description 5
125000004742 propyloxycarbonyl group Chemical group 0.000 description 5
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
229910052723 transition metal Inorganic materials 0.000 description 5
150000003624 transition metals Chemical class 0.000 description 5
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 description 4
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 4
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 4
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 4
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
125000002373 5 membered heterocyclic group Chemical group 0.000 description 4
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 4
206010012655 Diabetic complications Diseases 0.000 description 4
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 4
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
239000005456 alcohol based solvent Substances 0.000 description 4
150000001342 alkaline earth metals Chemical class 0.000 description 4
125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 4
125000002947 alkylene group Chemical group 0.000 description 4
206010003246 arthritis Diseases 0.000 description 4
125000002619 bicyclic group Chemical group 0.000 description 4
230000033228 biological regulation Effects 0.000 description 4
239000000872 buffer Substances 0.000 description 4
SKKTUOZKZKCGTB-UHFFFAOYSA-N butyl carbamate Chemical compound CCCCOC(N)=O SKKTUOZKZKCGTB-UHFFFAOYSA-N 0.000 description 4
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
238000010511 deprotection reaction Methods 0.000 description 4
235000005911 diet Nutrition 0.000 description 4
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000009472 formulation Methods 0.000 description 4
238000010575 fractional recrystallization Methods 0.000 description 4
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 4
239000005457 ice water Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
235000010355 mannitol Nutrition 0.000 description 4
125000001624 naphthyl group Chemical group 0.000 description 4
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 4
238000000926 separation method Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 4
229930192474 thiophene Natural products 0.000 description 4
AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical compound N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 description 4
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 3
125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 description 3
BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 3
YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 3
FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 3
MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 3
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 3
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 3
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 3
SXBOFEGFGHKWRX-UHFFFAOYSA-N 2-amino-1-[4-(2-methoxyphenyl)piperazin-1-yl]ethanone;dihydrochloride Chemical compound Cl.Cl.COC1=CC=CC=C1N1CCN(C(=O)CN)CC1 SXBOFEGFGHKWRX-UHFFFAOYSA-N 0.000 description 3
PIXMYJIJMMPBQY-UHFFFAOYSA-N 2-amino-1-[4-(2-methylphenyl)piperidin-1-yl]ethanone;hydrochloride Chemical compound Cl.CC1=CC=CC=C1C1CCN(C(=O)CN)CC1 PIXMYJIJMMPBQY-UHFFFAOYSA-N 0.000 description 3
NZICTXXANBRCMT-UHFFFAOYSA-N 2-amino-1-[4-(4-chlorophenyl)piperidin-1-yl]ethanone;hydrochloride Chemical compound Cl.C1CN(C(=O)CN)CCC1C1=CC=C(Cl)C=C1 NZICTXXANBRCMT-UHFFFAOYSA-N 0.000 description 3
GIACWQJJIMNILB-UHFFFAOYSA-N 2-amino-1-[4-(4-fluorophenyl)piperazin-1-yl]ethanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(=O)CN)CCN1C1=CC=C(F)C=C1 GIACWQJJIMNILB-UHFFFAOYSA-N 0.000 description 3
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 3
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 3
LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 3
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 3
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
KPJMKEOLALLMDY-UHFFFAOYSA-N 3-(4-hydroxy-3-nitrophenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=C(O)C([N+]([O-])=O)=C1 KPJMKEOLALLMDY-UHFFFAOYSA-N 0.000 description 3
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 3
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 3
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 3
NJBQIOKBFXTYIA-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)piperidin-1-yl]-1-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butan-1-one Chemical compound C1=CC(Cl)=CC=C1C1CCN(CCCC(=O)C=2C=C3CCNCCC3=CC=2)CC1 NJBQIOKBFXTYIA-UHFFFAOYSA-N 0.000 description 3
FPWNLURCHDRMHC-UHFFFAOYSA-N 4-chlorobiphenyl Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC=C1 FPWNLURCHDRMHC-UHFFFAOYSA-N 0.000 description 3
GUCPYIYFQVTFSI-UHFFFAOYSA-N 4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1 GUCPYIYFQVTFSI-UHFFFAOYSA-N 0.000 description 3
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 3
CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
229940122199 Insulin secretagogue Drugs 0.000 description 3
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 3
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 3
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 3
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 3
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
229930006000 Sucrose Natural products 0.000 description 3
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 3
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
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 3
230000002378 acidificating effect Effects 0.000 description 3
125000005196 alkyl carbonyloxy group Chemical group 0.000 description 3
125000001118 alkylidene group Chemical group 0.000 description 3
125000000304 alkynyl group Chemical group 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 description 3
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 3
150000003863 ammonium salts Chemical class 0.000 description 3
125000005161 aryl oxy carbonyl group Chemical group 0.000 description 3
125000005279 aryl sulfonyloxy group Chemical group 0.000 description 3
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
239000001768 carboxy methyl cellulose Substances 0.000 description 3
238000010531 catalytic reduction reaction Methods 0.000 description 3
210000004978 chinese hamster ovary cell Anatomy 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
125000000392 cycloalkenyl group Chemical group 0.000 description 3
230000037213 diet Effects 0.000 description 3
125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 3
125000006202 diisopropylaminoethyl group Chemical group [H]C([H])([H])C([H])(N(C([H])([H])C([H])([H])*)C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 3
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 3
238000006266 etherification reaction Methods 0.000 description 3
MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 3
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 3
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
150000007529 inorganic bases Chemical class 0.000 description 3
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 3
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 3
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 description 3
GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
JJYKJUXBWFATTE-UHFFFAOYSA-N mosher's acid Chemical compound COC(C(O)=O)(C(F)(F)F)C1=CC=CC=C1 JJYKJUXBWFATTE-UHFFFAOYSA-N 0.000 description 3
YNTOKMNHRPSGFU-UHFFFAOYSA-N n-Propyl carbamate Chemical compound CCCOC(N)=O YNTOKMNHRPSGFU-UHFFFAOYSA-N 0.000 description 3
239000002773 nucleotide Substances 0.000 description 3
125000003729 nucleotide group Chemical group 0.000 description 3
238000006053 organic reaction Methods 0.000 description 3
235000006408 oxalic acid Nutrition 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 3
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 3
239000010452 phosphate Substances 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
SAALQYKUFCIMHR-UHFFFAOYSA-N propan-2-ol;2-propan-2-yloxypropane Chemical compound CC(C)O.CC(C)OC(C)C SAALQYKUFCIMHR-UHFFFAOYSA-N 0.000 description 3
238000000746 purification Methods 0.000 description 3
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 3
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 3
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 3
230000009467 reduction Effects 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
235000019333 sodium laurylsulphate Nutrition 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
239000005720 sucrose Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
SOMDCVZTMLWKKV-DQZFIDPSSA-N (2s)-2-amino-3-hydroxypropanoic acid;(2s,3s)-2-amino-3-methylpentanoic acid Chemical compound OC[C@H](N)C(O)=O.CC[C@H](C)[C@H](N)C(O)=O SOMDCVZTMLWKKV-DQZFIDPSSA-N 0.000 description 2
QBHBHOSRLDPIHG-UHFFFAOYSA-N (4-hydroxy-3-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(O)C([N+]([O-])=O)=C1 QBHBHOSRLDPIHG-UHFFFAOYSA-N 0.000 description 2
NOKHSGUJEWXYLK-UHFFFAOYSA-N (4-nitrophenyl) 3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC(=O)N1C2=CC=CC=C2CCC1 NOKHSGUJEWXYLK-UHFFFAOYSA-N 0.000 description 2
125000006591 (C2-C6) alkynylene group Chemical group 0.000 description 2
RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 description 2
ODIYSGAEEJRHKE-AATRIKPKSA-N (e)-n,n-dimethyl-3-(2,3,4,5-tetrahydro-1h-1-benzazepin-8-yl)prop-2-en-1-amine Chemical compound C1CCCNC2=CC(/C=C/CN(C)C)=CC=C21 ODIYSGAEEJRHKE-AATRIKPKSA-N 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
RXBYRTSOWREATF-UHFFFAOYSA-N 1,2,3,4-tetrahydroacridine Chemical compound C1=CC=C2C=C(CCCC3)C3=NC2=C1 RXBYRTSOWREATF-UHFFFAOYSA-N 0.000 description 2
125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 description 2
CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 2
125000005837 1,2-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([*:2])C1([H])[H] 0.000 description 2
FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 2
AVNWRUHCAZGGRO-UHFFFAOYSA-N 1-(1-acetyl-2,3,4,5-tetrahydro-1-benzazepin-8-yl)-3-chloropropan-1-one Chemical compound CC(=O)N1CCCCC2=CC=C(C(=O)CCCl)C=C12 AVNWRUHCAZGGRO-UHFFFAOYSA-N 0.000 description 2
VNFBCFSIWFVDRX-UHFFFAOYSA-N 1-(3-acetyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-4-[4-(4-chlorophenyl)piperidin-1-yl]butan-1-one Chemical compound C1=C2CCN(C(=O)C)CCC2=CC=C1C(=O)CCCN(CC1)CCC1C1=CC=C(Cl)C=C1 VNFBCFSIWFVDRX-UHFFFAOYSA-N 0.000 description 2
JWYOPCINNSNSNL-UHFFFAOYSA-N 1-(3-acetyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-4-[4-(4-chlorophenyl)piperidin-1-yl]butane-1,4-dione Chemical compound C1=C2CCN(C(=O)C)CCC2=CC=C1C(=O)CCC(=O)N(CC1)CCC1C1=CC=C(Cl)C=C1 JWYOPCINNSNSNL-UHFFFAOYSA-N 0.000 description 2
GBPGFTISZWVWAM-UHFFFAOYSA-N 1-(3-acetyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-4-chlorobutan-1-one Chemical compound C1CN(C(=O)C)CCC2=CC=C(C(=O)CCCCl)C=C21 GBPGFTISZWVWAM-UHFFFAOYSA-N 0.000 description 2
HVDIFZZTVMCHLT-UHFFFAOYSA-N 1-(3-benzyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-4-[4-(4-chlorophenyl)piperidin-1-yl]butane-1,4-dione Chemical compound C1=CC(Cl)=CC=C1C1CCN(C(=O)CCC(=O)C=2C=C3CCN(CC=4C=CC=CC=4)CCC3=CC=2)CC1 HVDIFZZTVMCHLT-UHFFFAOYSA-N 0.000 description 2
BCAGZFZTIMYPLR-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-(1,2,3,4-tetrahydroisoquinolin-7-yl)butane-1,4-dione Chemical compound C1=CC(Cl)=CC=C1C1CCN(C(=O)CCC(=O)C=2C=C3CNCCC3=CC=2)CC1 BCAGZFZTIMYPLR-UHFFFAOYSA-N 0.000 description 2
TYANQXWLRXMAJK-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-(2,3,4,5-tetrahydro-1h-2-benzazepin-8-yl)butane-1,4-dione Chemical compound C1=CC(Cl)=CC=C1C1CCN(C(=O)CCC(=O)C=2C=C3CNCCCC3=CC=2)CC1 TYANQXWLRXMAJK-UHFFFAOYSA-N 0.000 description 2
BDPAOYXGJJVLCG-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione Chemical compound C1=CC(Cl)=CC=C1C1CCN(C(=O)CCC(=O)C=2C=C3CCNCCC3=CC=2)CC1 BDPAOYXGJJVLCG-UHFFFAOYSA-N 0.000 description 2
PMJDLGXCYJSEDH-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)butane-1,4-dione Chemical compound C1=C2CCN(C)CCC2=CC=C1C(=O)CCC(=O)N(CC1)CCC1C1=CC=C(Cl)C=C1 PMJDLGXCYJSEDH-UHFFFAOYSA-N 0.000 description 2
HPCQZJPBHNTFRG-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-(3-propan-2-yl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)butane-1,4-dione Chemical compound C1=C2CCN(C(C)C)CCC2=CC=C1C(=O)CCC(=O)N(CC1)CCC1C1=CC=C(Cl)C=C1 HPCQZJPBHNTFRG-UHFFFAOYSA-N 0.000 description 2
SRGYOURUKONTFE-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-(3-propyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)butane-1,4-dione Chemical compound C1=C2CCN(CCC)CCC2=CC=C1C(=O)CCC(=O)N(CC1)CCC1C1=CC=C(Cl)C=C1 SRGYOURUKONTFE-UHFFFAOYSA-N 0.000 description 2
WLGNHIXLJUOGHE-UHFFFAOYSA-N 1-[7-[3-[4-(4-methoxyphenyl)piperidin-1-yl]propoxy]-1,2,4,5-tetrahydro-3-benzazepin-3-yl]ethanone Chemical compound C1=CC(OC)=CC=C1C1CCN(CCCOC=2C=C3CCN(CCC3=CC=2)C(C)=O)CC1 WLGNHIXLJUOGHE-UHFFFAOYSA-N 0.000 description 2
PMGMDDQASWCRMH-UHFFFAOYSA-N 1-[7-[3-[4-(4-methylphenyl)piperidin-1-yl]propoxy]-1,2,4,5-tetrahydro-3-benzazepin-3-yl]ethanone Chemical compound C1=C2CCN(C(=O)C)CCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(C)C=C1 PMGMDDQASWCRMH-UHFFFAOYSA-N 0.000 description 2
XJMNSMPTPZVLJI-UHFFFAOYSA-N 1-[8-[3-[4-(4-methoxyphenyl)piperidin-1-yl]propoxy]-1,3,4,5-tetrahydro-2-benzazepin-2-yl]ethanone Chemical compound C1=CC(OC)=CC=C1C1CCN(CCCOC=2C=C3CN(CCCC3=CC=2)C(C)=O)CC1 XJMNSMPTPZVLJI-UHFFFAOYSA-N 0.000 description 2
NIWYGNDPYHVHKJ-UHFFFAOYSA-N 1-[8-[3-[4-(4-methylphenyl)piperidin-1-yl]propoxy]-1,3,4,5-tetrahydro-2-benzazepin-2-yl]ethanone Chemical compound C1=C2CN(C(=O)C)CCCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(C)C=C1 NIWYGNDPYHVHKJ-UHFFFAOYSA-N 0.000 description 2
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 2
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 2
125000000579 2,2-diphenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 2
HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 2
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 description 2
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 2
ZHBIWFGGIKFSHZ-UHFFFAOYSA-N 3-(4-chlorophenyl)propan-1-ol Chemical compound OCCCC1=CC=C(Cl)C=C1 ZHBIWFGGIKFSHZ-UHFFFAOYSA-N 0.000 description 2
SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
UKYMMHXYTXOTFT-UHFFFAOYSA-N 4-(dimethylamino)-1-(1,2,3,4-tetrahydroquinolin-6-yl)butan-1-one Chemical compound N1CCCC2=CC(C(=O)CCCN(C)C)=CC=C21 UKYMMHXYTXOTFT-UHFFFAOYSA-N 0.000 description 2
ASIGWAMOEPENOF-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)piperidin-1-yl]-1-(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)butan-1-one Chemical compound C1=C2CCN(C)CCC2=CC=C1C(=O)CCCN(CC1)CCC1C1=CC=C(Cl)C=C1 ASIGWAMOEPENOF-UHFFFAOYSA-N 0.000 description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
WCSZRRMKILFMKB-UHFFFAOYSA-N 4-oxo-4-[2-(2,2,2-trifluoroacetyl)-3,4-dihydro-1h-isoquinolin-7-yl]butanoic acid Chemical compound C1CN(C(=O)C(F)(F)F)CC2=CC(C(=O)CCC(=O)O)=CC=C21 WCSZRRMKILFMKB-UHFFFAOYSA-N 0.000 description 2
FZVRVHIDUGOAEB-UHFFFAOYSA-N 4-oxo-n-(3-phenylpropyl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)NCCCC1=CC=CC=C1 FZVRVHIDUGOAEB-UHFFFAOYSA-N 0.000 description 2
DDDHECIQUMWHIG-UHFFFAOYSA-N 4-oxo-n-(pyridin-4-ylmethyl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)NCC1=CC=NC=C1 DDDHECIQUMWHIG-UHFFFAOYSA-N 0.000 description 2
KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 2
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
239000005541 ACE inhibitor Substances 0.000 description 2
ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 2
229940077274 Alpha glucosidase inhibitor Drugs 0.000 description 2
229940123413 Angiotensin II antagonist Drugs 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
102100034159 Beta-3 adrenergic receptor Human genes 0.000 description 2
229940123208 Biguanide Drugs 0.000 description 2
241000283690 Bos taurus Species 0.000 description 2
125000003601 C2-C6 alkynyl group Chemical group 0.000 description 2
229940127291 Calcium channel antagonist Drugs 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
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
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 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
241000282412 Homo Species 0.000 description 2
101000976075 Homo sapiens Insulin Proteins 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
229940122355 Insulin sensitizer Drugs 0.000 description 2
DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 2
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 2
102000016267 Leptin Human genes 0.000 description 2
108010092277 Leptin Proteins 0.000 description 2
239000004472 Lysine Substances 0.000 description 2
238000006683 Mannich reaction Methods 0.000 description 2
ZPXSCAKFGYXMGA-UHFFFAOYSA-N Mazindol Chemical compound N12CCN=C2C2=CC=CC=C2C1(O)C1=CC=C(Cl)C=C1 ZPXSCAKFGYXMGA-UHFFFAOYSA-N 0.000 description 2
238000006751 Mitsunobu reaction Methods 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical compound CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
229940127315 Potassium Channel Openers Drugs 0.000 description 2
108010007568 Protamines Proteins 0.000 description 2
102000007327 Protamines Human genes 0.000 description 2
229940123924 Protein kinase C inhibitor Drugs 0.000 description 2
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
229940100389 Sulfonylurea Drugs 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
UOVHUKALBVIUIA-ONEGZZNKSA-N [4-(4-chlorophenyl)phenyl]-[5-[(e)-3-(dimethylamino)prop-1-enyl]-2,3-dihydroindol-1-yl]methanone Chemical compound C1CC2=CC(/C=C/CN(C)C)=CC=C2N1C(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1 UOVHUKALBVIUIA-ONEGZZNKSA-N 0.000 description 2
NHENIDFQHLFNCW-HWKANZROSA-N [4-(4-chlorophenyl)phenyl]-[6-[(e)-3-(dimethylamino)prop-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CCC2=CC(/C=C/CN(C)C)=CC=C2N1C(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1 NHENIDFQHLFNCW-HWKANZROSA-N 0.000 description 2
MSMPLXRSOJIFRU-GQCTYLIASA-N [4-(4-chlorophenyl)phenyl]-[6-[(e)-3-piperidin-1-ylprop-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(C(=O)N2C3=CC=C(\C=C\CN4CCCCC4)C=C3CCC2)C=C1 MSMPLXRSOJIFRU-GQCTYLIASA-N 0.000 description 2
GNUVBNXJOYFDAO-ZZXKWVIFSA-N [4-(4-chlorophenyl)phenyl]-[6-[(e)-4-(dimethylamino)but-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CCC2=CC(/C=C/CCN(C)C)=CC=C2N1C(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1 GNUVBNXJOYFDAO-ZZXKWVIFSA-N 0.000 description 2
PYGUNRFYGSTNSM-VOTSOKGWSA-N [5-[(e)-3-(dimethylamino)prop-1-enyl]-2,3-dihydroindol-1-yl]-(4-phenylphenyl)methanone Chemical compound C1CC2=CC(/C=C/CN(C)C)=CC=C2N1C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 PYGUNRFYGSTNSM-VOTSOKGWSA-N 0.000 description 2
YSQIEXYEOUHZRG-SNAWJCMRSA-N [5-[(e)-3-(dimethylamino)prop-1-enyl]-2,3-dihydroindol-1-yl]-[4-[(4-methoxyphenyl)methoxy]phenyl]methanone Chemical compound C1=CC(OC)=CC=C1COC1=CC=C(C(=O)N2C3=CC=C(\C=C\CN(C)C)C=C3CC2)C=C1 YSQIEXYEOUHZRG-SNAWJCMRSA-N 0.000 description 2
238000000862 absorption spectrum Methods 0.000 description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
239000012042 active reagent Substances 0.000 description 2
239000000048 adrenergic agonist Substances 0.000 description 2
229940126157 adrenergic receptor agonist Drugs 0.000 description 2
239000003288 aldose reductase inhibitor Substances 0.000 description 2
229940090865 aldose reductase inhibitors used in diabetes Drugs 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
239000003888 alpha glucosidase inhibitor Substances 0.000 description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
238000005576 amination reaction Methods 0.000 description 2
239000002333 angiotensin II receptor antagonist Substances 0.000 description 2
229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 2
125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
230000001430 anti-depressive effect Effects 0.000 description 2
239000000935 antidepressant agent Substances 0.000 description 2
229940005513 antidepressants Drugs 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
235000006708 antioxidants Nutrition 0.000 description 2
239000002249 anxiolytic agent Substances 0.000 description 2
230000036528 appetite Effects 0.000 description 2
235000019789 appetite Nutrition 0.000 description 2
125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
125000001769 aryl amino group Chemical group 0.000 description 2
235000003704 aspartic acid Nutrition 0.000 description 2
159000000009 barium salts Chemical class 0.000 description 2
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 2
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
229940092714 benzenesulfonic acid Drugs 0.000 description 2
CYKIHIBNSFRKQP-UHFFFAOYSA-N benzo[f][1]benzothiole Chemical compound C1=CC=C2C=C(SC=C3)C3=CC2=C1 CYKIHIBNSFRKQP-UHFFFAOYSA-N 0.000 description 2
SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
108010014502 beta-3 Adrenergic Receptors Proteins 0.000 description 2
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 2
150000004283 biguanides Chemical class 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 2
STXLEBDCAKUIQT-UHFFFAOYSA-N butanamide;2,2,2-trifluoroacetic acid Chemical compound CCCC(N)=O.OC(=O)C(F)(F)F STXLEBDCAKUIQT-UHFFFAOYSA-N 0.000 description 2
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
159000000007 calcium salts Chemical class 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 description 2
KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 2
WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 2
150000001925 cycloalkenes Chemical class 0.000 description 2
OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 2
SUYVUBYJARFZHO-RRKCRQDMSA-N dATP Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@H]1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1 SUYVUBYJARFZHO-RRKCRQDMSA-N 0.000 description 2
RGWHQCVHVJXOKC-SHYZEUOFSA-N dCTP Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OP(O)(O)=O)[C@@H](O)C1 RGWHQCVHVJXOKC-SHYZEUOFSA-N 0.000 description 2
HAAZLUGHYHWQIW-KVQBGUIXSA-N dGTP Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@H]1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1 HAAZLUGHYHWQIW-KVQBGUIXSA-N 0.000 description 2
NHVNXKFIZYSCEB-XLPZGREQSA-N dTTP Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)C1 NHVNXKFIZYSCEB-XLPZGREQSA-N 0.000 description 2
PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Chemical compound CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 description 2
238000011161 development Methods 0.000 description 2
ZWWWLCMDTZFSOO-UHFFFAOYSA-N diethoxyphosphorylformonitrile Chemical compound CCOP(=O)(C#N)OCC ZWWWLCMDTZFSOO-UHFFFAOYSA-N 0.000 description 2
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 2
239000007884 disintegrant Substances 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
YQBRPZBLROENTD-UHFFFAOYSA-N ethyl 3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OCC)CCCC2=C1 YQBRPZBLROENTD-UHFFFAOYSA-N 0.000 description 2
YHVGNPDEZVHBKY-UHFFFAOYSA-N ethyl 6-[3-(dimethylamino)propanoyl]-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound CN(C)CCC(=O)C1=CC=C2N(C(=O)OCC)CCCC2=C1 YHVGNPDEZVHBKY-UHFFFAOYSA-N 0.000 description 2
TUYBNCXSBVRODK-UHFFFAOYSA-N ethyl 6-[3-(dimethylamino)propyl]-3,4-dihydro-2h-quinoline-1-carboxylate;hydrochloride Chemical compound Cl.CN(C)CCCC1=CC=C2N(C(=O)OCC)CCCC2=C1 TUYBNCXSBVRODK-UHFFFAOYSA-N 0.000 description 2
125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 2
125000006125 ethylsulfonyl group Chemical group 0.000 description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
229940125753 fibrate Drugs 0.000 description 2
229960002464 fluoxetine Drugs 0.000 description 2
150000002244 furazanes Chemical class 0.000 description 2
210000004211 gastric acid Anatomy 0.000 description 2
230000036252 glycation Effects 0.000 description 2
UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 2
229940093915 gynecological organic acid Drugs 0.000 description 2
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
239000001863 hydroxypropyl cellulose Substances 0.000 description 2
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
PBGKTOXHQIOBKM-FHFVDXKLSA-N insulin (human) Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3NC=NC=3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CN=CN1 PBGKTOXHQIOBKM-FHFVDXKLSA-N 0.000 description 2
239000010410 layer Substances 0.000 description 2
NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 description 2
229940039781 leptin Drugs 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
229940031703 low substituted hydroxypropyl cellulose Drugs 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
159000000003 magnesium salts Chemical class 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
230000003211 malignant effect Effects 0.000 description 2
IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
229960000299 mazindol Drugs 0.000 description 2
108020004999 messenger RNA Proteins 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
229940017219 methyl propionate Drugs 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
235000010981 methylcellulose Nutrition 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
WPGGHFDDFPHPOB-BBWFWOEESA-N mitiglinide Chemical compound C([C@@H](CC(=O)N1C[C@@H]2CCCC[C@@H]2C1)C(=O)O)C1=CC=CC=C1 WPGGHFDDFPHPOB-BBWFWOEESA-N 0.000 description 2
125000002757 morpholinyl group Chemical group 0.000 description 2
MERQOEMRZFRSOZ-UHFFFAOYSA-N n,n-dimethyl-3-(1,2,3,4-tetrahydroquinolin-6-yl)propan-1-amine;dihydrochloride Chemical compound Cl.Cl.N1CCCC2=CC(CCCN(C)C)=CC=C21 MERQOEMRZFRSOZ-UHFFFAOYSA-N 0.000 description 2
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
125000005476 oxopyrrolidinyl group Chemical group 0.000 description 2
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
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 2
210000000496 pancreas Anatomy 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 2
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
230000004962 physiological condition Effects 0.000 description 2
HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 2
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
108090000765 processed proteins & peptides Proteins 0.000 description 2
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
239000003881 protein kinase C inhibitor Substances 0.000 description 2
USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 2
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 2
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 2
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 2
125000000714 pyrimidinyl group Chemical group 0.000 description 2
125000000168 pyrrolyl group Chemical group 0.000 description 2
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
230000001105 regulatory effect Effects 0.000 description 2
229920002477 rna polymer Polymers 0.000 description 2
239000004001 serotonin 1D antagonist Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
125000005504 styryl group Chemical group 0.000 description 2
125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 2
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 2
238000012546 transfer Methods 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 2
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000005406 washing Methods 0.000 description 2
229910052727 yttrium Inorganic materials 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 1
VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 description 1
RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 description 1
XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 description 1
ZBOYJODMIAUJHH-SANMLTNESA-N (2s)-1-[[2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound C=1C(OC)=C(CN2[C@@H](CCCC2)C(O)=O)C(OC)=CC=1OCC(C=1C)=CC=CC=1C1=CC=CC=C1 ZBOYJODMIAUJHH-SANMLTNESA-N 0.000 description 1
WAAPEIZFCHNLKK-UFBFGSQYSA-N (2s,4s)-6-fluoro-2',5'-dioxospiro[2,3-dihydrochromene-4,4'-imidazolidine]-2-carboxamide Chemical compound C([C@H](OC1=CC=C(F)C=C11)C(=O)N)[C@@]21NC(=O)NC2=O WAAPEIZFCHNLKK-UFBFGSQYSA-N 0.000 description 1
ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 1
MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
DIWRORZWFLOCLC-HNNXBMFYSA-N (3s)-7-chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound N([C@H](C(NC1=CC=C(Cl)C=C11)=O)O)=C1C1=CC=CC=C1Cl DIWRORZWFLOCLC-HNNXBMFYSA-N 0.000 description 1
NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 1
GMVPRGQOIOIIMI-UHFFFAOYSA-N (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(O)=O GMVPRGQOIOIIMI-UHFFFAOYSA-N 0.000 description 1
125000003161 (C1-C6) alkylene group Chemical group 0.000 description 1
IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
GQYFLYMQQJOPQB-BMRADRMJSA-N (e)-1-[1-[4-(4-chlorophenyl)benzoyl]-3,4-dihydro-2h-quinolin-6-yl]-3-(dimethylamino)prop-2-en-1-one Chemical compound C1CCC2=CC(C(=O)/C=C/N(C)C)=CC=C2N1C(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1 GQYFLYMQQJOPQB-BMRADRMJSA-N 0.000 description 1
ZBYRASCATLQYOT-CAPFRKAQSA-N (e)-1-[1-[4-(4-chlorophenyl)benzoyl]-3,4-dihydro-2h-quinolin-6-yl]-3-piperidin-1-ylprop-2-en-1-one Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(C(=O)N2C3=CC=C(C=C3CCC2)C(=O)\C=C\N2CCCCC2)C=C1 ZBYRASCATLQYOT-CAPFRKAQSA-N 0.000 description 1
KYGVLUVYSCSWDM-BQYQJAHWSA-N (e)-1-[4-(4-chlorophenyl)piperidin-1-yl]-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)but-2-ene-1,4-dione Chemical compound C1=CC(Cl)=CC=C1C1CCN(C(=O)\C=C\C(=O)C=2C=C3CCNCCC3=CC=2)CC1 KYGVLUVYSCSWDM-BQYQJAHWSA-N 0.000 description 1
VBVXNAOKMUGRAT-MDZDMXLPSA-N (e)-1-[4-(4-chlorophenyl)piperidin-1-yl]-4-(3-propan-2-yl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)but-2-ene-1,4-dione Chemical compound C1=C2CCN(C(C)C)CCC2=CC=C1C(=O)\C=C\C(=O)N(CC1)CCC1C1=CC=C(Cl)C=C1 VBVXNAOKMUGRAT-MDZDMXLPSA-N 0.000 description 1
YAKQGVSFEFAING-BQYQJAHWSA-N (e)-1-[4-(4-chlorophenyl)piperidin-1-yl]-4-[3-(2,2,2-trifluoroacetyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl]but-2-ene-1,4-dione Chemical compound C1=C2CCN(C(=O)C(F)(F)F)CCC2=CC=C1C(=O)\C=C\C(=O)N(CC1)CCC1C1=CC=C(Cl)C=C1 YAKQGVSFEFAING-BQYQJAHWSA-N 0.000 description 1
BETWIFJTPNJLNN-ONEGZZNKSA-N (e)-3-(2,3-dihydro-1h-indol-5-yl)-n,n-dimethylprop-2-en-1-amine Chemical compound CN(C)C\C=C\C1=CC=C2NCCC2=C1 BETWIFJTPNJLNN-ONEGZZNKSA-N 0.000 description 1
ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
108091032973 (ribonucleotides)n+m Proteins 0.000 description 1
MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
LRGZZEOWQURWFK-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7-octahydroisoquinoline Chemical compound C1NCCC2CCCC=C21 LRGZZEOWQURWFK-UHFFFAOYSA-N 0.000 description 1
ZCZVGQCBSJLDDS-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,8-naphthyridine Chemical compound C1=CC=C2CCCNC2=N1 ZCZVGQCBSJLDDS-UHFFFAOYSA-N 0.000 description 1
WXRSSOIHEAVYLL-UHFFFAOYSA-N 1,2,3,4-tetrahydrocinnoline Chemical compound C1=CC=C2NNCCC2=C1 WXRSSOIHEAVYLL-UHFFFAOYSA-N 0.000 description 1
JBHCHNYONQSXLP-UHFFFAOYSA-N 1,2,3,4-tetrahydrophenanthridine Chemical compound N1=CC2=CC=CC=C2C2=C1CCCC2 JBHCHNYONQSXLP-UHFFFAOYSA-N 0.000 description 1
IMSHIOJKUPGIOQ-UHFFFAOYSA-N 1,2,3,4-tetrahydrophenazine Chemical compound C1=CC=C2N=C(CCCC3)C3=NC2=C1 IMSHIOJKUPGIOQ-UHFFFAOYSA-N 0.000 description 1
STIWEDICJHIFJT-UHFFFAOYSA-N 1,2,3,4-tetrahydrophthalazine Chemical compound C1=CC=C2CNNCC2=C1 STIWEDICJHIFJT-UHFFFAOYSA-N 0.000 description 1
JQIZHNLEFQMDCQ-UHFFFAOYSA-N 1,2,3,4-tetrahydropyridazine Chemical compound C1CC=CNN1 JQIZHNLEFQMDCQ-UHFFFAOYSA-N 0.000 description 1
OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 description 1
PKORYTIUMAOPED-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinazoline Chemical compound C1=CC=C2NCNCC2=C1 PKORYTIUMAOPED-UHFFFAOYSA-N 0.000 description 1
HORKYAIEVBUXGM-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoxaline Chemical compound C1=CC=C2NCCNC2=C1 HORKYAIEVBUXGM-UHFFFAOYSA-N 0.000 description 1
125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
IOEPOEDBBPRAEI-UHFFFAOYSA-N 1,2-dihydroisoquinoline Chemical compound C1=CC=C2CNC=CC2=C1 IOEPOEDBBPRAEI-UHFFFAOYSA-N 0.000 description 1
CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 description 1
CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 description 1
125000005838 1,3-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:2])C([H])([H])C1([H])[*:1] 0.000 description 1
DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical compound C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 description 1
VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 1
NABUFFLEHQEQPH-UHFFFAOYSA-N 1-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)ethanone Chemical compound C1CN(C(=O)C)CCC2=CC=CC=C21 NABUFFLEHQEQPH-UHFFFAOYSA-N 0.000 description 1
MIDPOZWCMVDFNV-UHFFFAOYSA-N 1-(1-acetyl-2,3,4,5-tetrahydro-1-benzazepin-8-yl)-3-(dimethylamino)propan-1-one Chemical compound C1CCCN(C(C)=O)C2=CC(C(=O)CCN(C)C)=CC=C21 MIDPOZWCMVDFNV-UHFFFAOYSA-N 0.000 description 1
YEMCZYVINHZKOO-UHFFFAOYSA-N 1-(1-acetyl-2,3-dihydroindol-5-yl)-3-(dimethylamino)propan-1-one Chemical compound CN(C)CCC(=O)C1=CC=C2N(C(C)=O)CCC2=C1 YEMCZYVINHZKOO-UHFFFAOYSA-N 0.000 description 1
APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
GAIRNNQNGAMPMW-UHFFFAOYSA-N 1-(2,3,4,5-tetrahydro-1-benzazepin-1-yl)ethanone Chemical compound CC(=O)N1CCCCC2=CC=CC=C12 GAIRNNQNGAMPMW-UHFFFAOYSA-N 0.000 description 1
RNTCWULFNYNFGI-UHFFFAOYSA-N 1-(2,3-dihydroindol-1-yl)ethanone Chemical compound C1=CC=C2N(C(=O)C)CCC2=C1 RNTCWULFNYNFGI-UHFFFAOYSA-N 0.000 description 1
NHUNRKQDOMBJHS-UHFFFAOYSA-N 1-(2,6-dimethylmorpholin-4-yl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C(C)OC(C)CN1C(=O)CCC(=O)C1=CC=C(CCNCC2)C2=C1 NHUNRKQDOMBJHS-UHFFFAOYSA-N 0.000 description 1
IUNUZIKNJIUMQN-UHFFFAOYSA-N 1-(2-benzyl-1,3-dihydroisoindol-5-yl)-4-[4-(4-chlorophenyl)piperidin-1-yl]butane-1,4-dione Chemical compound C1=CC(Cl)=CC=C1C1CCN(C(=O)CCC(=O)C=2C=C3CN(CC=4C=CC=CC=4)CC3=CC=2)CC1 IUNUZIKNJIUMQN-UHFFFAOYSA-N 0.000 description 1
XNZVOPPEZMRLCA-UHFFFAOYSA-N 1-(2-benzyl-3,4-dihydro-1h-isoquinolin-7-yl)-4-[4-(4-chlorophenyl)piperidin-1-yl]butane-1,4-dione Chemical compound C1=CC(Cl)=CC=C1C1CCN(C(=O)CCC(=O)C=2C=C3CN(CC=4C=CC=CC=4)CCC3=CC=2)CC1 XNZVOPPEZMRLCA-UHFFFAOYSA-N 0.000 description 1
VNZLQLYBRIOLFZ-UHFFFAOYSA-N 1-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCNCC1 VNZLQLYBRIOLFZ-UHFFFAOYSA-N 0.000 description 1
REQZDPKTZDRXOL-UHFFFAOYSA-N 1-(2-phenylpiperidin-1-yl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione Chemical compound C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)N1CCCCC1C1=CC=CC=C1 REQZDPKTZDRXOL-UHFFFAOYSA-N 0.000 description 1
POQOAVFHWYRFGN-UHFFFAOYSA-N 1-(2-phenylpiperidin-1-yl)-4-[3-(2,2,2-trifluoroacetyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl]butane-1,4-dione Chemical compound C1=C2CCN(C(=O)C(F)(F)F)CCC2=CC=C1C(=O)CCC(=O)N1CCCCC1C1=CC=CC=C1 POQOAVFHWYRFGN-UHFFFAOYSA-N 0.000 description 1
ARYGXGVUUKTPHJ-UHFFFAOYSA-N 1-(3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-2-yl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CNCCC2=CC(C(=O)CCC(=O)N3CC4CCCCC4CC3)=CC=C21 ARYGXGVUUKTPHJ-UHFFFAOYSA-N 0.000 description 1
YSUUSXJJFAQFBX-UHFFFAOYSA-N 1-(3,4-dihydro-1h-isoquinolin-2-yl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CNCCC2=CC(C(=O)CCC(=O)N3CC4=CC=CC=C4CC3)=CC=C21 YSUUSXJJFAQFBX-UHFFFAOYSA-N 0.000 description 1
RPNDVWJAMQZOBU-UHFFFAOYSA-N 1-(3,5-dimethylpiperidin-1-yl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C(C)CC(C)CN1C(=O)CCC(=O)C1=CC=C(CCNCC2)C2=C1 RPNDVWJAMQZOBU-UHFFFAOYSA-N 0.000 description 1
BOHGBEJMIHMDQC-UHFFFAOYSA-N 1-(3-benzoyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-4-[4-(4-chlorophenyl)piperidin-1-yl]butane-1,4-dione Chemical compound C1=CC(Cl)=CC=C1C1CCN(C(=O)CCC(=O)C=2C=C3CCN(CCC3=CC=2)C(=O)C=2C=CC=CC=2)CC1 BOHGBEJMIHMDQC-UHFFFAOYSA-N 0.000 description 1
CBNRPAIKOARKOP-UHFFFAOYSA-N 1-(4-benzhydrylpiperazin-1-yl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)N(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 CBNRPAIKOARKOP-UHFFFAOYSA-N 0.000 description 1
ZTSMKTMFOLEDPI-UHFFFAOYSA-N 1-(4-benzylpiperazin-1-yl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)N(CC1)CCN1CC1=CC=CC=C1 ZTSMKTMFOLEDPI-UHFFFAOYSA-N 0.000 description 1
YQHUWRDKEPPBLO-UHFFFAOYSA-N 1-(4-benzylpiperidin-1-yl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)N(CC1)CCC1CC1=CC=CC=C1 YQHUWRDKEPPBLO-UHFFFAOYSA-N 0.000 description 1
JYQMAQVVIMGHIM-UHFFFAOYSA-N 1-(4-chlorophenyl)piperidine Chemical compound C1=CC(Cl)=CC=C1N1CCCCC1 JYQMAQVVIMGHIM-UHFFFAOYSA-N 0.000 description 1
FGDTWGFIKCHCLO-UHFFFAOYSA-N 1-(4-chlorophenyl)piperidine;hydrochloride Chemical compound Cl.C1=CC(Cl)=CC=C1N1CCCCC1 FGDTWGFIKCHCLO-UHFFFAOYSA-N 0.000 description 1
COPFMBASTWVFAX-UHFFFAOYSA-N 1-(4-ethylpiperazin-1-yl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CN(CC)CCN1C(=O)CCC(=O)C1=CC=C(CCNCC2)C2=C1 COPFMBASTWVFAX-UHFFFAOYSA-N 0.000 description 1
AVJKDKWRVSSJPK-UHFFFAOYSA-N 1-(4-fluorophenyl)piperazine Chemical compound C1=CC(F)=CC=C1N1CCNCC1 AVJKDKWRVSSJPK-UHFFFAOYSA-N 0.000 description 1
FVHWMJOVLDFKOR-UHFFFAOYSA-N 1-(4-hydroxypiperidin-1-yl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CC(O)CCN1C(=O)CCC(=O)C1=CC=C(CCNCC2)C2=C1 FVHWMJOVLDFKOR-UHFFFAOYSA-N 0.000 description 1
QWXMHNCGYLWWGE-UHFFFAOYSA-N 1-(4-phenylpiperazin-1-yl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)N(CC1)CCN1C1=CC=CC=C1 QWXMHNCGYLWWGE-UHFFFAOYSA-N 0.000 description 1
YBRVGQWTNQNOKQ-UHFFFAOYSA-N 1-(4-piperidin-1-ylpiperidin-1-yl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)N(CC1)CCC1N1CCCCC1 YBRVGQWTNQNOKQ-UHFFFAOYSA-N 0.000 description 1
WIMXLVARHZJUFG-UHFFFAOYSA-N 1-(4-pyridin-2-ylpiperazin-1-yl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)N(CC1)CCN1C1=CC=CC=N1 WIMXLVARHZJUFG-UHFFFAOYSA-N 0.000 description 1
WHCPXKVOSYKWBH-UHFFFAOYSA-N 1-(4-pyrimidin-2-ylpiperazin-1-yl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)N(CC1)CCN1C1=NC=CC=N1 WHCPXKVOSYKWBH-UHFFFAOYSA-N 0.000 description 1
XODZSJBRBFKBIN-UHFFFAOYSA-N 1-(4-pyrrolidin-1-ylpiperidin-1-yl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)N(CC1)CCC1N1CCCC1 XODZSJBRBFKBIN-UHFFFAOYSA-N 0.000 description 1
KMXPHBJUGYLXDM-UHFFFAOYSA-N 1-(7-hydroxy-6,6-dimethyl-7,8-dihydropyrano[2,3-f][2,1,3]benzoxadiazol-8-yl)piperidin-2-one Chemical compound OC1C(C)(C)OC2=CC3=NON=C3C=C2C1N1CCCCC1=O KMXPHBJUGYLXDM-UHFFFAOYSA-N 0.000 description 1
XMWGTKZEDLCVIG-UHFFFAOYSA-N 1-(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=CC2=C1 XMWGTKZEDLCVIG-UHFFFAOYSA-N 0.000 description 1
QWAOZOIAELHURW-JIDHJSLPSA-N 1-[(2s)-2-[(2,6-dimethylanilino)methyl]pyrrolidin-1-yl]-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC=CC(C)=C1NC[C@H]1N(C(=O)CCC(=O)C=2C=C3CCNCCC3=CC=2)CCC1 QWAOZOIAELHURW-JIDHJSLPSA-N 0.000 description 1
BOVGTQGAOIONJV-BETUJISGSA-N 1-[(3ar,6as)-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl]-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1C[C@H]2CCC[C@H]2C1 BOVGTQGAOIONJV-BETUJISGSA-N 0.000 description 1
ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
IKNQYJNMZZPUMT-UHFFFAOYSA-N 1-[1-[4-(4-chlorophenyl)benzoyl]-3,4-dihydro-2h-quinolin-6-yl]-4-(dimethylamino)butan-1-one Chemical compound C1CCC2=CC(C(=O)CCCN(C)C)=CC=C2N1C(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1 IKNQYJNMZZPUMT-UHFFFAOYSA-N 0.000 description 1
ABIMVRIAEBVDER-UHFFFAOYSA-N 1-[1-[4-(4-chlorophenyl)benzoyl]-3,4-dihydro-2h-quinolin-6-yl]ethanone Chemical compound C1CCC2=CC(C(=O)C)=CC=C2N1C(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1 ABIMVRIAEBVDER-UHFFFAOYSA-N 0.000 description 1
VDTWKXAPIQBOMO-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)-4,6-di(propan-2-yl)-3-propylphenyl]ethanol Chemical compound CCCC1=C(C(C)C)C=C(C(C)C)C(C(C)O)=C1C1=CC=C(F)C=C1 VDTWKXAPIQBOMO-UHFFFAOYSA-N 0.000 description 1
CLCNUCNLAOKRNM-UHFFFAOYSA-N 1-[2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)N1CCCC1CN1CCCC1 CLCNUCNLAOKRNM-UHFFFAOYSA-N 0.000 description 1
PFHHNDRKGZOWPW-UHFFFAOYSA-N 1-[3-(dimethylamino)pyrrolidin-1-yl]-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C(N(C)C)CCN1C(=O)CCC(=O)C1=CC=C(CCNCC2)C2=C1 PFHHNDRKGZOWPW-UHFFFAOYSA-N 0.000 description 1
JKVVUGCCEYSAJO-UHFFFAOYSA-N 1-[4-(2-hydroxyethyl)piperidin-1-yl]-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CC(CCO)CCN1C(=O)CCC(=O)C1=CC=C(CCNCC2)C2=C1 JKVVUGCCEYSAJO-UHFFFAOYSA-N 0.000 description 1
XKXHTTDOCCOSFL-UHFFFAOYSA-N 1-[4-(2-methoxyphenyl)piperazin-1-yl]-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC=C1N1CCN(C(=O)CCC(=O)C=2C=C3CCNCCC3=CC=2)CC1 XKXHTTDOCCOSFL-UHFFFAOYSA-N 0.000 description 1
DXCLJKBWMHJCGJ-UHFFFAOYSA-N 1-[4-(2-methylphenyl)piperidin-1-yl]-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione Chemical compound CC1=CC=CC=C1C1CCN(C(=O)CCC(=O)C=2C=C3CCNCCC3=CC=2)CC1 DXCLJKBWMHJCGJ-UHFFFAOYSA-N 0.000 description 1
MEPIECIOHQKPBN-UHFFFAOYSA-N 1-[4-(3-methylphenyl)piperidin-1-yl]-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione Chemical compound CC1=CC=CC(C2CCN(CC2)C(=O)CCC(=O)C=2C=C3CCNCCC3=CC=2)=C1 MEPIECIOHQKPBN-UHFFFAOYSA-N 0.000 description 1
HAFYTONSUMYDSD-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CN(C(=O)CCC(=O)C=2C=C3CCNCCC3=CC=2)CCC1(O)C1=CC=C(Cl)C=C1 HAFYTONSUMYDSD-UHFFFAOYSA-N 0.000 description 1
GBRLTMGDXAZZSR-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-(2-ethyl-1,3-dihydroisoindol-5-yl)butane-1,4-dione Chemical compound C1=C2CN(CC)CC2=CC=C1C(=O)CCC(=O)N(CC1)CCC1C1=CC=C(Cl)C=C1 GBRLTMGDXAZZSR-UHFFFAOYSA-N 0.000 description 1
SPBKVSPKMXCKQG-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-(2-ethyl-3,4-dihydro-1h-isoquinolin-7-yl)butane-1,4-dione Chemical compound C1=C2CN(CC)CCC2=CC=C1C(=O)CCC(=O)N(CC1)CCC1C1=CC=C(Cl)C=C1 SPBKVSPKMXCKQG-UHFFFAOYSA-N 0.000 description 1
JANKNKBSFCUPDP-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-(2-methyl-1,3,4,5-tetrahydro-2-benzazepin-8-yl)butane-1,4-dione Chemical compound C1=C2CN(C)CCCC2=CC=C1C(=O)CCC(=O)N(CC1)CCC1C1=CC=C(Cl)C=C1 JANKNKBSFCUPDP-UHFFFAOYSA-N 0.000 description 1
ONMBXBSBXQPXJW-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-(2-methyl-1,3-dihydroisoindol-5-yl)butane-1,4-dione Chemical compound C1=C2CN(C)CC2=CC=C1C(=O)CCC(=O)N(CC1)CCC1C1=CC=C(Cl)C=C1 ONMBXBSBXQPXJW-UHFFFAOYSA-N 0.000 description 1
SSQYIZYCBVUKNB-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)butane-1,4-dione Chemical compound C1=C2CN(C)CCC2=CC=C1C(=O)CCC(=O)N(CC1)CCC1C1=CC=C(Cl)C=C1 SSQYIZYCBVUKNB-UHFFFAOYSA-N 0.000 description 1
BDMXDNIBLYPLNN-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-(2-propan-2-yl-1,3-dihydroisoindol-5-yl)butane-1,4-dione Chemical compound C1=C2CN(C(C)C)CC2=CC=C1C(=O)CCC(=O)N(CC1)CCC1C1=CC=C(Cl)C=C1 BDMXDNIBLYPLNN-UHFFFAOYSA-N 0.000 description 1
WUNTZNOVFRYHOS-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-(2-propan-2-yl-3,4-dihydro-1h-isoquinolin-7-yl)butane-1,4-dione Chemical compound C1=C2CN(C(C)C)CCC2=CC=C1C(=O)CCC(=O)N(CC1)CCC1C1=CC=C(Cl)C=C1 WUNTZNOVFRYHOS-UHFFFAOYSA-N 0.000 description 1
QFSBWEIXQDDOQM-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-(3-cyclohexyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)butane-1,4-dione Chemical compound C1=CC(Cl)=CC=C1C1CCN(C(=O)CCC(=O)C=2C=C3CCN(CCC3=CC=2)C2CCCCC2)CC1 QFSBWEIXQDDOQM-UHFFFAOYSA-N 0.000 description 1
FETAVKMSJRJBIT-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-(3-cyclopentyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)butane-1,4-dione Chemical compound C1=CC(Cl)=CC=C1C1CCN(C(=O)CCC(=O)C=2C=C3CCN(CCC3=CC=2)C2CCCC2)CC1 FETAVKMSJRJBIT-UHFFFAOYSA-N 0.000 description 1
YKKXTSZLNAOYED-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-(3-ethyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)butane-1,4-dione Chemical compound C1=C2CCN(CC)CCC2=CC=C1C(=O)CCC(=O)N(CC1)CCC1C1=CC=C(Cl)C=C1 YKKXTSZLNAOYED-UHFFFAOYSA-N 0.000 description 1
GUBYDENBIWXPRJ-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-(3-phenacyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)butane-1,4-dione Chemical compound C1=CC(Cl)=CC=C1C1CCN(C(=O)CCC(=O)C=2C=C3CCN(CC(=O)C=4C=CC=CC=4)CCC3=CC=2)CC1 GUBYDENBIWXPRJ-UHFFFAOYSA-N 0.000 description 1
AKXNLCKFHZNNAS-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-(4-prop-1-ynyl-2,3,4,5-tetrahydro-1h-3-benzazepin-8-yl)butane-1,4-dione Chemical compound C1=C2CCNC(C#CC)CC2=CC=C1C(=O)CCC(=O)N(CC1)CCC1C1=CC=C(Cl)C=C1 AKXNLCKFHZNNAS-UHFFFAOYSA-N 0.000 description 1
GUWJMHKDUXVBRA-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-[2-(2,2,2-trifluoroacetyl)-1,3,4,5-tetrahydro-2-benzazepin-8-yl]butane-1,4-dione Chemical compound C1=C2CN(C(=O)C(F)(F)F)CCCC2=CC=C1C(=O)CCC(=O)N(CC1)CCC1C1=CC=C(Cl)C=C1 GUWJMHKDUXVBRA-UHFFFAOYSA-N 0.000 description 1
XQEYLNIMHISASD-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-[2-(2,2,2-trifluoroacetyl)-1,3-dihydroisoindol-5-yl]butane-1,4-dione Chemical compound C1=C2CN(C(=O)C(F)(F)F)CC2=CC=C1C(=O)CCC(=O)N(CC1)CCC1C1=CC=C(Cl)C=C1 XQEYLNIMHISASD-UHFFFAOYSA-N 0.000 description 1
WQXCQBLLBYSEJB-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-[2-(2,2,2-trifluoroacetyl)-3,4-dihydro-1h-isoquinolin-7-yl]butane-1,4-dione Chemical compound C1=C2CN(C(=O)C(F)(F)F)CCC2=CC=C1C(=O)CCC(=O)N(CC1)CCC1C1=CC=C(Cl)C=C1 WQXCQBLLBYSEJB-UHFFFAOYSA-N 0.000 description 1
VZMWSTQJBHAPLA-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-[3-(2,2,2-trifluoroacetyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl]butane-1,4-dione Chemical compound C1=C2CCN(C(=O)C(F)(F)F)CCC2=CC=C1C(=O)CCC(=O)N(CC1)CCC1C1=CC=C(Cl)C=C1 VZMWSTQJBHAPLA-UHFFFAOYSA-N 0.000 description 1
UHJAGTZQGTUAFK-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-[3-(2-methylpropyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl]butane-1,4-dione Chemical compound C1=C2CCN(CC(C)C)CCC2=CC=C1C(=O)CCC(=O)N(CC1)CCC1C1=CC=C(Cl)C=C1 UHJAGTZQGTUAFK-UHFFFAOYSA-N 0.000 description 1
QANUPFLMTAXBHT-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-[3-(2-oxopropyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl]butane-1,4-dione Chemical compound C1=C2CCN(CC(=O)C)CCC2=CC=C1C(=O)CCC(=O)N(CC1)CCC1C1=CC=C(Cl)C=C1 QANUPFLMTAXBHT-UHFFFAOYSA-N 0.000 description 1
WGIUBROTZJVLFO-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-[3-(2-pyrrol-1-ylethyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl]butane-1,4-dione Chemical compound C1=CC(Cl)=CC=C1C1CCN(C(=O)CCC(=O)C=2C=C3CCN(CCN4C=CC=C4)CCC3=CC=2)CC1 WGIUBROTZJVLFO-UHFFFAOYSA-N 0.000 description 1
FPCCAYNEOYVFMY-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-[3-(cyclohexylmethyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl]butane-1,4-dione Chemical compound C1=CC(Cl)=CC=C1C1CCN(C(=O)CCC(=O)C=2C=C3CCN(CC4CCCCC4)CCC3=CC=2)CC1 FPCCAYNEOYVFMY-UHFFFAOYSA-N 0.000 description 1
AMLALZHFPOMAKU-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-[3-(oxolan-2-ylmethyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl]butane-1,4-dione Chemical compound C1=CC(Cl)=CC=C1C1CCN(C(=O)CCC(=O)C=2C=C3CCN(CC4OCCC4)CCC3=CC=2)CC1 AMLALZHFPOMAKU-UHFFFAOYSA-N 0.000 description 1
INSMKAINXKQZQC-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-[3-[(2-methylphenyl)methyl]-1,2,4,5-tetrahydro-3-benzazepin-7-yl]butane-1,4-dione Chemical compound CC1=CC=CC=C1CN1CCC2=CC(C(=O)CCC(=O)N3CCC(CC3)C=3C=CC(Cl)=CC=3)=CC=C2CC1 INSMKAINXKQZQC-UHFFFAOYSA-N 0.000 description 1
PPGHUMKEJQLTDT-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-[3-[(3-methylphenyl)methyl]-1,2,4,5-tetrahydro-3-benzazepin-7-yl]butane-1,4-dione Chemical compound CC1=CC=CC(CN2CCC3=CC(=CC=C3CC2)C(=O)CCC(=O)N2CCC(CC2)C=2C=CC(Cl)=CC=2)=C1 PPGHUMKEJQLTDT-UHFFFAOYSA-N 0.000 description 1
TWMMBWDKRSYPJH-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)piperidin-1-yl]-4-[3-[(4-methylphenyl)methyl]-1,2,4,5-tetrahydro-3-benzazepin-7-yl]butane-1,4-dione Chemical compound C1=CC(C)=CC=C1CN1CCC2=CC(C(=O)CCC(=O)N3CCC(CC3)C=3C=CC(Cl)=CC=3)=CC=C2CC1 TWMMBWDKRSYPJH-UHFFFAOYSA-N 0.000 description 1
INUZXEKBHTWJDR-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)piperidin-1-yl]-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione Chemical compound C1=CC(F)=CC=C1C1CCN(C(=O)CCC(=O)C=2C=C3CCNCCC3=CC=2)CC1 INUZXEKBHTWJDR-UHFFFAOYSA-N 0.000 description 1
VBOZGHIWAJCGNW-UHFFFAOYSA-N 1-[4-(4-methoxyphenyl)piperidin-1-yl]-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione Chemical compound C1=CC(OC)=CC=C1C1CCN(C(=O)CCC(=O)C=2C=C3CCNCCC3=CC=2)CC1 VBOZGHIWAJCGNW-UHFFFAOYSA-N 0.000 description 1
AYUKIPYHSRBRPZ-UHFFFAOYSA-N 1-[4-(4-methylphenyl)piperidin-1-yl]-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione Chemical compound C1=CC(C)=CC=C1C1CCN(C(=O)CCC(=O)C=2C=C3CCNCCC3=CC=2)CC1 AYUKIPYHSRBRPZ-UHFFFAOYSA-N 0.000 description 1
SCRXMROORKREKA-UHFFFAOYSA-N 1-[4-(4-methylphenyl)piperidin-1-yl]-4-(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)butane-1,4-dione Chemical compound C1=C2CCN(C)CCC2=CC=C1C(=O)CCC(=O)N(CC1)CCC1C1=CC=C(C)C=C1 SCRXMROORKREKA-UHFFFAOYSA-N 0.000 description 1
JPOHNMLUWRLQKL-UHFFFAOYSA-N 1-[4-(4-methylphenyl)piperidin-1-yl]-4-(3-propan-2-yl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)butane-1,4-dione;hydrochloride Chemical compound Cl.C1=C2CCN(C(C)C)CCC2=CC=C1C(=O)CCC(=O)N(CC1)CCC1C1=CC=C(C)C=C1 JPOHNMLUWRLQKL-UHFFFAOYSA-N 0.000 description 1
ORXSYJIRGNXMLA-KQGICBIGSA-N 1-[4-[(e)-3-phenylprop-2-enyl]piperazin-1-yl]-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)N(CC1)CCN1C\C=C\C1=CC=CC=C1 ORXSYJIRGNXMLA-KQGICBIGSA-N 0.000 description 1
COMXWQDPDNCIIB-UHFFFAOYSA-N 1-[4-oxo-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanoyl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1C(=O)CCC(=O)C1=CC=C(CCNCC2)C2=C1 COMXWQDPDNCIIB-UHFFFAOYSA-N 0.000 description 1
YSNBNAKYLPDFFJ-UHFFFAOYSA-N 1-[5-[3-(dimethylamino)-1-hydroxypropyl]-2,3-dihydroindol-1-yl]ethanone Chemical compound CN(C)CCC(O)C1=CC=C2N(C(C)=O)CCC2=C1 YSNBNAKYLPDFFJ-UHFFFAOYSA-N 0.000 description 1
GHBVHQZNWXPLFY-UHFFFAOYSA-N 1-[7-[3-[4-(2,4-difluorophenyl)piperidin-1-yl]propoxy]-1,2,4,5-tetrahydro-3-benzazepin-3-yl]ethanone Chemical compound C1=C2CCN(C(=O)C)CCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(F)C=C1F GHBVHQZNWXPLFY-UHFFFAOYSA-N 0.000 description 1
NVXUJONFXMQENL-UHFFFAOYSA-N 1-[7-[3-[4-(2-methylphenyl)piperidin-1-yl]propoxy]-1,2,4,5-tetrahydro-3-benzazepin-3-yl]ethanone Chemical compound C1=C2CCN(C(=O)C)CCC2=CC=C1OCCCN(CC1)CCC1C1=CC=CC=C1C NVXUJONFXMQENL-UHFFFAOYSA-N 0.000 description 1
IHDDFFLNNWYFCQ-UHFFFAOYSA-N 1-[7-[3-[4-(3-fluorophenyl)piperidin-1-yl]propoxy]-1,2,4,5-tetrahydro-3-benzazepin-3-yl]ethanone Chemical compound C1=C2CCN(C(=O)C)CCC2=CC=C1OCCCN(CC1)CCC1C1=CC=CC(F)=C1 IHDDFFLNNWYFCQ-UHFFFAOYSA-N 0.000 description 1
NCGUIRZSOVFKEM-UHFFFAOYSA-N 1-[7-[3-[4-(3-methylphenyl)piperidin-1-yl]propoxy]-1,2,4,5-tetrahydro-3-benzazepin-3-yl]ethanone Chemical compound C1=C2CCN(C(=O)C)CCC2=CC=C1OCCCN(CC1)CCC1C1=CC=CC(C)=C1 NCGUIRZSOVFKEM-UHFFFAOYSA-N 0.000 description 1
UVIDRZYOCXKLFU-UHFFFAOYSA-N 1-[7-[3-[4-(4-chlorophenyl)piperidin-1-yl]propoxy]-1,2,4,5-tetrahydro-3-benzazepin-3-yl]-2-methylpropan-1-one Chemical compound C1=C2CCN(C(=O)C(C)C)CCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(Cl)C=C1 UVIDRZYOCXKLFU-UHFFFAOYSA-N 0.000 description 1
KTYTYSRNCBIVNY-UHFFFAOYSA-N 1-[7-[3-[4-(4-chlorophenyl)piperidin-1-yl]propoxy]-1,2,4,5-tetrahydro-3-benzazepin-3-yl]ethanone Chemical compound C1=C2CCN(C(=O)C)CCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(Cl)C=C1 KTYTYSRNCBIVNY-UHFFFAOYSA-N 0.000 description 1
SLIWYNKHWQYIGR-UHFFFAOYSA-N 1-[7-[3-[4-(4-fluorophenyl)piperidin-1-yl]propoxy]-1,2,4,5-tetrahydro-3-benzazepin-3-yl]ethanone Chemical compound C1=C2CCN(C(=O)C)CCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(F)C=C1 SLIWYNKHWQYIGR-UHFFFAOYSA-N 0.000 description 1
PBHYEKZHMLESRJ-UHFFFAOYSA-N 1-[7-[3-[4-(4-methoxyphenyl)piperidin-1-yl]propoxy]-1,2,4,5-tetrahydro-3-benzazepin-3-yl]-2-methylpropan-1-one Chemical compound C1=CC(OC)=CC=C1C1CCN(CCCOC=2C=C3CCN(CCC3=CC=2)C(=O)C(C)C)CC1 PBHYEKZHMLESRJ-UHFFFAOYSA-N 0.000 description 1
OABQBMTZWKZIBD-VOTSOKGWSA-N 1-[8-[(e)-3-(dimethylamino)prop-1-enyl]-2,3,4,5-tetrahydro-1-benzazepin-1-yl]ethanone Chemical compound C1CCCN(C(C)=O)C2=CC(/C=C/CN(C)C)=CC=C21 OABQBMTZWKZIBD-VOTSOKGWSA-N 0.000 description 1
DUJTWCCFZIELFW-UHFFFAOYSA-N 1-[8-[3-[4-(2,4-difluorophenyl)piperidin-1-yl]propoxy]-1,3,4,5-tetrahydro-2-benzazepin-2-yl]ethanone Chemical compound C1=C2CN(C(=O)C)CCCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(F)C=C1F DUJTWCCFZIELFW-UHFFFAOYSA-N 0.000 description 1
LNAWQMAUJUIALE-UHFFFAOYSA-N 1-[8-[3-[4-(3-fluorophenyl)piperidin-1-yl]propoxy]-1,3,4,5-tetrahydro-2-benzazepin-2-yl]ethanone Chemical compound C1=C2CN(C(=O)C)CCCC2=CC=C1OCCCN(CC1)CCC1C1=CC=CC(F)=C1 LNAWQMAUJUIALE-UHFFFAOYSA-N 0.000 description 1
AKGRYODZXHLDEB-UHFFFAOYSA-N 1-[8-[3-[4-(3-methylphenyl)piperidin-1-yl]propoxy]-1,3,4,5-tetrahydro-2-benzazepin-2-yl]ethanone Chemical compound C1=C2CN(C(=O)C)CCCC2=CC=C1OCCCN(CC1)CCC1C1=CC=CC(C)=C1 AKGRYODZXHLDEB-UHFFFAOYSA-N 0.000 description 1
SVKOSHJAMSHZPX-UHFFFAOYSA-N 1-[8-[3-[4-(4-chlorophenyl)piperidin-1-yl]propoxy]-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-2-methylpropan-1-one Chemical compound C1=C2CN(C(=O)C(C)C)CCCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(Cl)C=C1 SVKOSHJAMSHZPX-UHFFFAOYSA-N 0.000 description 1
TXUHPSXMOSYTQC-UHFFFAOYSA-N 1-[8-[3-[4-(4-fluorophenyl)piperidin-1-yl]propoxy]-1,3,4,5-tetrahydro-2-benzazepin-2-yl]ethanone Chemical compound C1=C2CN(C(=O)C)CCCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(F)C=C1 TXUHPSXMOSYTQC-UHFFFAOYSA-N 0.000 description 1
LIGRFGUTYUZFBG-UHFFFAOYSA-N 1-[8-[3-[4-(4-methoxyphenyl)piperidin-1-yl]propoxy]-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-2-methylpropan-1-one Chemical compound C1=CC(OC)=CC=C1C1CCN(CCCOC=2C=C3CN(CCCC3=CC=2)C(=O)C(C)C)CC1 LIGRFGUTYUZFBG-UHFFFAOYSA-N 0.000 description 1
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
WDHIVCODFOHIBY-UHFFFAOYSA-N 1-morpholin-4-yl-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)N1CCOCC1 WDHIVCODFOHIBY-UHFFFAOYSA-N 0.000 description 1
125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
OBCLXVPUABDMCI-UHFFFAOYSA-N 1-piperidin-1-yl-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butane-1,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)N1CCCCC1 OBCLXVPUABDMCI-UHFFFAOYSA-N 0.000 description 1
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 description 1
UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
ORFVKIQYRLNLFK-UHFFFAOYSA-N 2,2,2-trifluoro-1-(1,3,4,5-tetrahydro-2-benzazepin-2-yl)ethanone Chemical compound C1N(C(=O)C(F)(F)F)CCCC2=CC=CC=C21 ORFVKIQYRLNLFK-UHFFFAOYSA-N 0.000 description 1
PFDUTIDPFATCMI-UHFFFAOYSA-N 2,2,2-trifluoro-1-isoindol-2-ylethanone Chemical compound C1=CC=CC2=CN(C(=O)C(F)(F)F)C=C21 PFDUTIDPFATCMI-UHFFFAOYSA-N 0.000 description 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 description 1
MAOODNQRFAGJFV-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-2-benzazepin-8-ol;hydrobromide Chemical compound Br.C1CCNCC2=CC(O)=CC=C21 MAOODNQRFAGJFV-UHFFFAOYSA-N 0.000 description 1
MWVMYAWMFTVYED-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCCC2=CC=CC=C21 MWVMYAWMFTVYED-UHFFFAOYSA-N 0.000 description 1
CFTOTSJVQRFXOF-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole Chemical compound N1C2=CC=CC=C2C2=C1CNCC2 CFTOTSJVQRFXOF-UHFFFAOYSA-N 0.000 description 1
XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 description 1
LCXSFEMSLWDBJG-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-thioxanthene Chemical compound C1C2=CC=CC=C2SC2=C1CCCC2 LCXSFEMSLWDBJG-UHFFFAOYSA-N 0.000 description 1
HRCMXYXVAWHBTH-UHFFFAOYSA-N 2,3-dihydro-1,3-benzoxazole Chemical compound C1=CC=C2OCNC2=C1 HRCMXYXVAWHBTH-UHFFFAOYSA-N 0.000 description 1
KEQTWHPMSVAFDA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical compound C1NNC=C1 KEQTWHPMSVAFDA-UHFFFAOYSA-N 0.000 description 1
VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 1
VUPXKQHLZATXTR-UHFFFAOYSA-N 2,4-diphenyl-1,3-oxazole Chemical compound C=1OC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 VUPXKQHLZATXTR-UHFFFAOYSA-N 0.000 description 1
FFMBYMANYCDCMK-UHFFFAOYSA-N 2,5-dihydro-1h-imidazole Chemical compound C1NCN=C1 FFMBYMANYCDCMK-UHFFFAOYSA-N 0.000 description 1
QCCHBHSAIQIQGO-UHFFFAOYSA-N 2,7-difluorospiro[fluorene-9,5'-imidazolidine]-2',4'-dione Chemical compound C12=CC(F)=CC=C2C2=CC=C(F)C=C2C21NC(=O)NC2=O QCCHBHSAIQIQGO-UHFFFAOYSA-N 0.000 description 1
CHZXTOCAICMPQR-UHFFFAOYSA-N 2-(2-bromoethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCBr)C(=O)C2=C1 CHZXTOCAICMPQR-UHFFFAOYSA-N 0.000 description 1
KSHXAAXEJWSEND-UHFFFAOYSA-N 2-(4-chlorophenoxy)ethanamine Chemical compound NCCOC1=CC=C(Cl)C=C1 KSHXAAXEJWSEND-UHFFFAOYSA-N 0.000 description 1
GFHQSRIMUNIWRS-UHFFFAOYSA-N 2-(4-hydroxy-3-nitrophenyl)-n,n-dipropylacetamide Chemical compound CCCN(CCC)C(=O)CC1=CC=C(O)C([N+]([O-])=O)=C1 GFHQSRIMUNIWRS-UHFFFAOYSA-N 0.000 description 1
DVTYJMQWZHKOTG-UHFFFAOYSA-N 2-(Trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CN(C(=O)C(F)(F)F)CCC2=C1 DVTYJMQWZHKOTG-UHFFFAOYSA-N 0.000 description 1
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
CILPHQCEVYJUDN-VWYCJHECSA-N 2-[(1s,2s,5r)-5-methyl-2-propan-2-ylcyclohexyl]oxyacetic acid Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1OCC(O)=O CILPHQCEVYJUDN-VWYCJHECSA-N 0.000 description 1
VRPJIFMKZZEXLR-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)NCC(O)=O VRPJIFMKZZEXLR-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
LQQWLNCZSIDJEC-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)propyl]isoindole-1,3-dione Chemical compound C1=CC(Cl)=CC=C1CCCN1C(=O)C2=CC=CC=C2C1=O LQQWLNCZSIDJEC-UHFFFAOYSA-N 0.000 description 1
VWWMGPCUZVOLLK-UHFFFAOYSA-N 2-[4-[(2-cyclopropyl-7-methylimidazo[4,5-b]pyridin-3-yl)methyl]phenyl]benzoic acid Chemical compound C1CC1C1=NC=2C(C)=CC=NC=2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O VWWMGPCUZVOLLK-UHFFFAOYSA-N 0.000 description 1
NSVFSAJIGAJDMR-UHFFFAOYSA-N 2-[benzyl(phenyl)amino]ethyl 5-(5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound CC=1NC(C)=C(C(=O)OCCN(CC=2C=CC=CC=2)C=2C=CC=CC=2)C(C=2C=C(C=CC=2)[N+]([O-])=O)C=1P1(=O)OCC(C)(C)CO1 NSVFSAJIGAJDMR-UHFFFAOYSA-N 0.000 description 1
YGZFYDFBHIDIBH-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]icosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCC(CO)N(CCO)CCO YGZFYDFBHIDIBH-UHFFFAOYSA-N 0.000 description 1
DVOVBGJJSFSOPZ-UHFFFAOYSA-N 2-acetamidopropanamide Chemical compound NC(=O)C(C)NC(C)=O DVOVBGJJSFSOPZ-UHFFFAOYSA-N 0.000 description 1
UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
RUYACOIKDYMHBL-UHFFFAOYSA-N 2-benzyl-8-[3-[4-(4-chlorophenyl)piperidin-1-yl]propoxy]-1,3,4,5-tetrahydro-2-benzazepine Chemical compound C1=CC(Cl)=CC=C1C1CCN(CCCOC=2C=C3CN(CC=4C=CC=CC=4)CCCC3=CC=2)CC1 RUYACOIKDYMHBL-UHFFFAOYSA-N 0.000 description 1
125000005999 2-bromoethyl group Chemical group 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
FVTWJXMFYOXOKK-UHFFFAOYSA-N 2-fluoroacetamide Chemical compound NC(=O)CF FVTWJXMFYOXOKK-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
MNWSGMTUGXNYHJ-UHFFFAOYSA-N 2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(N)=O MNWSGMTUGXNYHJ-UHFFFAOYSA-N 0.000 description 1
OUXIVFUIHLGDOJ-UHFFFAOYSA-N 2-methyl-1-[7-[3-[4-(4-methylphenyl)piperidin-1-yl]propoxy]-1,2,4,5-tetrahydro-3-benzazepin-3-yl]propan-1-one Chemical compound C1=C2CCN(C(=O)C(C)C)CCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(C)C=C1 OUXIVFUIHLGDOJ-UHFFFAOYSA-N 0.000 description 1
MTFBXGLXQSCNTH-UHFFFAOYSA-N 2-methyl-1-[8-[3-[4-(4-methylphenyl)piperidin-1-yl]propoxy]-1,3,4,5-tetrahydro-2-benzazepin-2-yl]propan-1-one Chemical compound C1=C2CN(C(=O)C(C)C)CCCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(C)C=C1 MTFBXGLXQSCNTH-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
MPJOJCZVGBOVOV-UHFFFAOYSA-N 2-phenylbenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C1=CC=CC=C1 MPJOJCZVGBOVOV-UHFFFAOYSA-N 0.000 description 1
VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 1
FHLZGJKCZSRVAH-UHFFFAOYSA-N 2-propan-2-yl-8-[3-[4-[3-(trifluoromethyl)phenyl]piperidin-1-yl]propoxy]-1,3,4,5-tetrahydro-2-benzazepine Chemical compound C1=C2CN(C(C)C)CCCC2=CC=C1OCCCN(CC1)CCC1C1=CC=CC(C(F)(F)F)=C1 FHLZGJKCZSRVAH-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
YRLORWPBJZEGBX-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazine Chemical compound C1=CC=C2NCCOC2=C1 YRLORWPBJZEGBX-UHFFFAOYSA-N 0.000 description 1
CZRAWWBYKYRGHO-UHFFFAOYSA-N 3,4-dihydro-2h-quinolin-1-yl-(4-phenylpiperidin-1-yl)methanone Chemical compound C1CCC2=CC=CC=C2N1C(=O)N(CC1)CCC1C1=CC=CC=C1 CZRAWWBYKYRGHO-UHFFFAOYSA-N 0.000 description 1
ZLUUPCCXIKTEBG-UHFFFAOYSA-N 3,4-dihydro-2h-quinoline-1-carboxylic acid Chemical compound C1=CC=C2N(C(=O)O)CCCC2=C1 ZLUUPCCXIKTEBG-UHFFFAOYSA-N 0.000 description 1
BCSVCWVQNOXFGL-UHFFFAOYSA-N 3,4-dihydro-4-oxo-3-((5-trifluoromethyl-2-benzothiazolyl)methyl)-1-phthalazine acetic acid Chemical compound O=C1C2=CC=CC=C2C(CC(=O)O)=NN1CC1=NC2=CC(C(F)(F)F)=CC=C2S1 BCSVCWVQNOXFGL-UHFFFAOYSA-N 0.000 description 1
HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
RQHQOQMQHIANPO-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[3-[(3-propan-2-yl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)oxy]propyl]propan-1-amine Chemical compound C1=C2CCN(C(C)C)CCC2=CC=C1OCCCNCCCC1=CC=C(Cl)C=C1 RQHQOQMQHIANPO-UHFFFAOYSA-N 0.000 description 1
RVLNDSYSQLMPRC-UHFFFAOYSA-N 3-(4-chlorophenyl)propan-1-amine Chemical compound NCCCC1=CC=C(Cl)C=C1 RVLNDSYSQLMPRC-UHFFFAOYSA-N 0.000 description 1
BBSLOKZINKEUCR-UHFFFAOYSA-N 3-(4-chlorophenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=C(Cl)C=C1 BBSLOKZINKEUCR-UHFFFAOYSA-N 0.000 description 1
AEIMFLFBFOFLAF-UHFFFAOYSA-N 3-(4-naphthalen-2-ylsulfonyl-2,3-dihydro-1,4-benzoxazin-6-yl)-n-(pyridin-4-ylmethyl)propan-1-amine;dihydrochloride Chemical compound Cl.Cl.C=1C=C2C=CC=CC2=CC=1S(=O)(=O)N(C1=C2)CCOC1=CC=C2CCCNCC1=CC=NC=C1 AEIMFLFBFOFLAF-UHFFFAOYSA-N 0.000 description 1
AEDQNOLIADXSBB-UHFFFAOYSA-N 3-(dodecylazaniumyl)propanoate Chemical compound CCCCCCCCCCCCNCCC(O)=O AEDQNOLIADXSBB-UHFFFAOYSA-N 0.000 description 1
IYNJMNAHVQRMKT-UHFFFAOYSA-N 3-benzyl-7-[3-[4-(4-chlorophenyl)piperidin-1-yl]propoxy]-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1=CC(Cl)=CC=C1C1CCN(CCCOC=2C=C3CCN(CC=4C=CC=CC=4)CCC3=CC=2)CC1 IYNJMNAHVQRMKT-UHFFFAOYSA-N 0.000 description 1
INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 description 1
HJBLUNHMOKFZQX-UHFFFAOYSA-N 3-hydroxy-1,2,3-benzotriazin-4-one Chemical compound C1=CC=C2C(=O)N(O)N=NC2=C1 HJBLUNHMOKFZQX-UHFFFAOYSA-N 0.000 description 1
QLILRKBRWXALIE-UHFFFAOYSA-N 3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1 QLILRKBRWXALIE-UHFFFAOYSA-N 0.000 description 1
ZBRDJMFLJXFIGJ-UHFFFAOYSA-N 3-phenyl-1,2-oxazole Chemical compound O1C=CC(C=2C=CC=CC=2)=N1 ZBRDJMFLJXFIGJ-UHFFFAOYSA-N 0.000 description 1
FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 description 1
YAJFOKCTADGFTD-UHFFFAOYSA-N 3-propan-2-yl-7-[3-[4-[3-(trifluoromethyl)phenyl]piperidin-1-yl]propoxy]-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1=C2CCN(C(C)C)CCC2=CC=C1OCCCN(CC1)CCC1C1=CC=CC(C(F)(F)F)=C1 YAJFOKCTADGFTD-UHFFFAOYSA-N 0.000 description 1
JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 description 1
UVRZFBNVDIHBKO-UHFFFAOYSA-N 4-(4-chlorophenyl)-1-[3-(4-naphthalen-2-ylsulfonyl-2,3-dihydro-1,4-benzoxazin-6-yl)propyl]piperidin-4-ol;hydrochloride Chemical compound Cl.C1CN(CCCC=2C=C3N(CCOC3=CC=2)S(=O)(=O)C=2C=C3C=CC=CC3=CC=2)CCC1(O)C1=CC=C(Cl)C=C1 UVRZFBNVDIHBKO-UHFFFAOYSA-N 0.000 description 1
CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
FIMRRWLTRBEAOM-UHFFFAOYSA-N 4-(4-chlorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(Cl)C=C1 FIMRRWLTRBEAOM-UHFFFAOYSA-N 0.000 description 1
JOWMTYWOBJALGB-UHFFFAOYSA-N 4-(4-methylcyclohexyl)-4-oxobutanoic acid Chemical compound CC1CCC(C(=O)CCC(O)=O)CC1 JOWMTYWOBJALGB-UHFFFAOYSA-N 0.000 description 1
QBQLYIISSRXYKL-UHFFFAOYSA-N 4-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-1,2-oxazolidine-3,5-dione Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC1C(=O)NOC1=O QBQLYIISSRXYKL-UHFFFAOYSA-N 0.000 description 1
FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 description 1
KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
CDIIZULDSLKBKV-UHFFFAOYSA-N 4-chlorobutanoyl chloride Chemical compound ClCCCC(Cl)=O CDIIZULDSLKBKV-UHFFFAOYSA-N 0.000 description 1
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
229960000549 4-dimethylaminophenol Drugs 0.000 description 1
125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
JSSRVWMUGJSSJX-UHFFFAOYSA-N 4-naphthalen-2-ylsulfonyl-6-[3-(4-phenylpiperidin-1-yl)propyl]-2,3-dihydro-1,4-benzoxazine;hydrochloride Chemical compound Cl.C=1C=C2C=CC=CC2=CC=1S(=O)(=O)N(C1=C2)CCOC1=CC=C2CCCN(CC1)CCC1C1=CC=CC=C1 JSSRVWMUGJSSJX-UHFFFAOYSA-N 0.000 description 1
KUJVGPCGUWYMSX-UHFFFAOYSA-N 4-naphthalen-2-ylsulfonyl-6-[3-(4-piperidin-1-ylpiperidin-1-yl)propyl]-2,3-dihydro-1,4-benzoxazine;dihydrochloride Chemical compound Cl.Cl.C=1C=C2C=CC=CC2=CC=1S(=O)(=O)N(C1=C2)CCOC1=CC=C2CCCN(CC1)CCC1N1CCCCC1 KUJVGPCGUWYMSX-UHFFFAOYSA-N 0.000 description 1
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
ISCNDLZBLJLFKR-UHFFFAOYSA-N 4-oxo-4-[2-(2,2,2-trifluoroacetyl)-1,3,4,5-tetrahydro-2-benzazepin-8-yl]butanoic acid Chemical compound C1CCN(C(=O)C(F)(F)F)CC2=CC(C(=O)CCC(=O)O)=CC=C21 ISCNDLZBLJLFKR-UHFFFAOYSA-N 0.000 description 1
CAYREEXJYDPAGP-UHFFFAOYSA-N 4-oxo-n,n-bis(pyridin-2-ylmethyl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)N(CC=1N=CC=CC=1)CC1=CC=CC=N1 CAYREEXJYDPAGP-UHFFFAOYSA-N 0.000 description 1
ZGZLHMCVYFEUNW-UHFFFAOYSA-N 4-oxo-n,n-bis(pyridin-3-ylmethyl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)N(CC=1C=NC=CC=1)CC1=CC=CN=C1 ZGZLHMCVYFEUNW-UHFFFAOYSA-N 0.000 description 1
RZCGAPCROSZIAH-UHFFFAOYSA-N 4-oxo-n-(2-phenoxyethyl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)NCCOC1=CC=CC=C1 RZCGAPCROSZIAH-UHFFFAOYSA-N 0.000 description 1
CCMVGRCLNRSDRE-UHFFFAOYSA-N 4-oxo-n-(2-phenoxyethyl)-4-(3-propan-2-yl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)butanamide Chemical compound C1=C2CCN(C(C)C)CCC2=CC=C1C(=O)CCC(=O)NCCOC1=CC=CC=C1 CCMVGRCLNRSDRE-UHFFFAOYSA-N 0.000 description 1
JVAJYKXQMLKRON-UHFFFAOYSA-N 4-oxo-n-(2-piperidin-1-ylethyl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)NCCN1CCCCC1 JVAJYKXQMLKRON-UHFFFAOYSA-N 0.000 description 1
DNCPBHYLNKGPRQ-UHFFFAOYSA-N 4-oxo-n-(2-pyrrolidin-1-ylethyl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)NCCN1CCCC1 DNCPBHYLNKGPRQ-UHFFFAOYSA-N 0.000 description 1
IICOOYOXVXJOIO-UHFFFAOYSA-N 4-oxo-n-(4-phenylbutan-2-yl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide;hydrochloride Chemical compound Cl.C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)NC(C)CCC1=CC=CC=C1 IICOOYOXVXJOIO-UHFFFAOYSA-N 0.000 description 1
GDIIGRIHTFHMHU-UHFFFAOYSA-N 4-oxo-n-(4-phenylbutyl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)NCCCCC1=CC=CC=C1 GDIIGRIHTFHMHU-UHFFFAOYSA-N 0.000 description 1
QNGZKOIREKNXIG-UHFFFAOYSA-N 4-oxo-n-(pyridin-2-ylmethyl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)NCC1=CC=CC=N1 QNGZKOIREKNXIG-UHFFFAOYSA-N 0.000 description 1
ZPBWLGRTXVDLFT-UHFFFAOYSA-N 4-oxo-n-(pyridin-3-ylmethyl)-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)NCC1=CC=CN=C1 ZPBWLGRTXVDLFT-UHFFFAOYSA-N 0.000 description 1
XKUVZPBMZFEKFF-UHFFFAOYSA-N 4-oxo-n-[3-(2-oxopyrrolidin-1-yl)propyl]-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)NCCCN1CCCC1=O XKUVZPBMZFEKFF-UHFFFAOYSA-N 0.000 description 1
ZSOJCXALONOUKQ-UHFFFAOYSA-N 4-oxo-n-prop-2-ynyl-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C1CNCCC2=CC(C(=O)CCC(=O)NCC#C)=CC=C21 ZSOJCXALONOUKQ-UHFFFAOYSA-N 0.000 description 1
NFFXEUUOMTXWCX-UHFFFAOYSA-N 5-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-methoxy-n-[[4-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound C1=C(C(=O)NCC=2C=CC(=CC=2)C(F)(F)F)C(OC)=CC=C1CC1SC(=O)NC1=O NFFXEUUOMTXWCX-UHFFFAOYSA-N 0.000 description 1
IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
IETKPTYAGKZLKY-UHFFFAOYSA-N 5-[[4-[(3-methyl-4-oxoquinazolin-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=CC=C2C(=O)N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O IETKPTYAGKZLKY-UHFFFAOYSA-N 0.000 description 1
ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 1
NTKMCTMYLXLNCJ-UHFFFAOYSA-N 6-(3-iodopropyl)-4-naphthalen-2-ylsulfonyl-2,3-dihydro-1,4-benzoxazine Chemical compound C1=CC=CC2=CC(S(=O)(=O)N3CCOC4=CC=C(C=C43)CCCI)=CC=C21 NTKMCTMYLXLNCJ-UHFFFAOYSA-N 0.000 description 1
CZIWDQZOOYKJJD-UHFFFAOYSA-N 6-[3-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]propyl]-4-naphthalen-2-ylsulfonyl-2,3-dihydro-1,4-benzoxazine;dihydrochloride Chemical compound Cl.Cl.C1=CC=CC2=CC(S(=O)(N3C4=CC(CCCN5CCN(CC=6C=C7OCOC7=CC=6)CC5)=CC=C4OCC3)=O)=CC=C21 CZIWDQZOOYKJJD-UHFFFAOYSA-N 0.000 description 1
PEFMFSYFQBXBCU-UHFFFAOYSA-N 7-[3-[4-(2,4-difluorophenyl)piperidin-1-yl]propoxy]-3-propan-2-yl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1=C2CCN(C(C)C)CCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(F)C=C1F PEFMFSYFQBXBCU-UHFFFAOYSA-N 0.000 description 1
PLEWTIUVBIMRNF-UHFFFAOYSA-N 7-[3-[4-(2-methylphenyl)piperidin-1-yl]propoxy]-3-propan-2-yl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1=C2CCN(C(C)C)CCC2=CC=C1OCCCN(CC1)CCC1C1=CC=CC=C1C PLEWTIUVBIMRNF-UHFFFAOYSA-N 0.000 description 1
XUHLCUXMBMHJTB-UHFFFAOYSA-N 7-[3-[4-(3-methylphenyl)piperidin-1-yl]propoxy]-3-propan-2-yl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1=C2CCN(C(C)C)CCC2=CC=C1OCCCN(CC1)CCC1C1=CC=CC(C)=C1 XUHLCUXMBMHJTB-UHFFFAOYSA-N 0.000 description 1
UCUBSBJCXHPIEP-UHFFFAOYSA-N 7-[3-[4-(4-chlorophenyl)piperidin-1-yl]propoxy]-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1=CC(Cl)=CC=C1C1CCN(CCCOC=2C=C3CCNCCC3=CC=2)CC1 UCUBSBJCXHPIEP-UHFFFAOYSA-N 0.000 description 1
MWNRWBSJAWVPRV-UHFFFAOYSA-N 7-[3-[4-(4-chlorophenyl)piperidin-1-yl]propoxy]-3-cyclopentyl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1=CC(Cl)=CC=C1C1CCN(CCCOC=2C=C3CCN(CCC3=CC=2)C2CCCC2)CC1 MWNRWBSJAWVPRV-UHFFFAOYSA-N 0.000 description 1
BMQVWWSBGRSKIY-UHFFFAOYSA-N 7-[3-[4-(4-chlorophenyl)piperidin-1-yl]propoxy]-3-methyl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1=C2CCN(C)CCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(Cl)C=C1 BMQVWWSBGRSKIY-UHFFFAOYSA-N 0.000 description 1
GJHWINMHUABKAD-UHFFFAOYSA-N 7-[3-[4-(4-chlorophenyl)piperidin-1-yl]propoxy]-3-methylsulfonyl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1=C2CCN(S(=O)(=O)C)CCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(Cl)C=C1 GJHWINMHUABKAD-UHFFFAOYSA-N 0.000 description 1
ZJMIWSLBEMBKOH-UHFFFAOYSA-N 7-[3-[4-(4-chlorophenyl)piperidin-1-yl]propoxy]-3-propan-2-yl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1=C2CCN(C(C)C)CCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(Cl)C=C1 ZJMIWSLBEMBKOH-UHFFFAOYSA-N 0.000 description 1
XKTLPDFSWIFIEO-UHFFFAOYSA-N 7-[3-[4-(4-chlorophenyl)piperidin-1-yl]propoxy]-n-ethyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1=C2CCN(C(=O)NCC)CCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(Cl)C=C1 XKTLPDFSWIFIEO-UHFFFAOYSA-N 0.000 description 1
CIRIDGWRKRTLOU-UHFFFAOYSA-N 7-[3-[4-(4-fluorophenyl)piperidin-1-yl]propoxy]-3-propan-2-yl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1=C2CCN(C(C)C)CCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(F)C=C1 CIRIDGWRKRTLOU-UHFFFAOYSA-N 0.000 description 1
OOQKLYLAGKNSDC-UHFFFAOYSA-N 7-[3-[4-(4-methoxyphenyl)piperidin-1-yl]propoxy]-3-methylsulfonyl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1=CC(OC)=CC=C1C1CCN(CCCOC=2C=C3CCN(CCC3=CC=2)S(C)(=O)=O)CC1 OOQKLYLAGKNSDC-UHFFFAOYSA-N 0.000 description 1
SBUHHQURCAUYNM-UHFFFAOYSA-N 7-[3-[4-(4-methoxyphenyl)piperidin-1-yl]propoxy]-3-propan-2-yl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1=CC(OC)=CC=C1C1CCN(CCCOC=2C=C3CCN(CCC3=CC=2)C(C)C)CC1 SBUHHQURCAUYNM-UHFFFAOYSA-N 0.000 description 1
XLUVZTPIPHZHOK-UHFFFAOYSA-N 7-[3-[4-(4-methylphenyl)piperidin-1-yl]propoxy]-3-methylsulfonyl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1=CC(C)=CC=C1C1CCN(CCCOC=2C=C3CCN(CCC3=CC=2)S(C)(=O)=O)CC1 XLUVZTPIPHZHOK-UHFFFAOYSA-N 0.000 description 1
PMTXWGJYVQCLIW-UHFFFAOYSA-N 7-[3-[4-(4-methylphenyl)piperidin-1-yl]propoxy]-3-propan-2-yl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1=C2CCN(C(C)C)CCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(C)C=C1 PMTXWGJYVQCLIW-UHFFFAOYSA-N 0.000 description 1
SNZSSCZJMVIOCR-UHFFFAOYSA-N 7-azabicyclo[2.2.1]heptane Chemical compound C1CC2CCC1N2 SNZSSCZJMVIOCR-UHFFFAOYSA-N 0.000 description 1
XBWAZCLHZCFCGK-UHFFFAOYSA-N 7-chloro-1-methyl-5-phenyl-3,4-dihydro-2h-1,4-benzodiazepin-1-ium;chloride Chemical compound [Cl-].C12=CC(Cl)=CC=C2[NH+](C)CCN=C1C1=CC=CC=C1 XBWAZCLHZCFCGK-UHFFFAOYSA-N 0.000 description 1
BUCORZSTKDOEKQ-UHFFFAOYSA-N 7-chloro-4-hydroxy-N-methyl-5-phenyl-3H-1,4-benzodiazepin-2-imine Chemical compound C=12C=C(Cl)C=CC2=NC(=NC)CN(O)C=1C1=CC=CC=C1 BUCORZSTKDOEKQ-UHFFFAOYSA-N 0.000 description 1
FAAZMFZFDSHHPT-UHFFFAOYSA-N 8-[3-[4-(2,4-difluorophenyl)piperidin-1-yl]propoxy]-2-propan-2-yl-1,3,4,5-tetrahydro-2-benzazepine Chemical compound C1=C2CN(C(C)C)CCCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(F)C=C1F FAAZMFZFDSHHPT-UHFFFAOYSA-N 0.000 description 1
BZDGROOMLZKKMB-UHFFFAOYSA-N 8-[3-[4-(2-methylphenyl)piperidin-1-yl]propoxy]-2-propan-2-yl-1,3,4,5-tetrahydro-2-benzazepine Chemical compound C1=C2CN(C(C)C)CCCC2=CC=C1OCCCN(CC1)CCC1C1=CC=CC=C1C BZDGROOMLZKKMB-UHFFFAOYSA-N 0.000 description 1
FIOJBRXQJVWRSK-UHFFFAOYSA-N 8-[3-[4-(3-methylphenyl)piperidin-1-yl]propoxy]-2-propan-2-yl-1,3,4,5-tetrahydro-2-benzazepine Chemical compound C1=C2CN(C(C)C)CCCC2=CC=C1OCCCN(CC1)CCC1C1=CC=CC(C)=C1 FIOJBRXQJVWRSK-UHFFFAOYSA-N 0.000 description 1
SCKSYGMBVDCKIZ-UHFFFAOYSA-N 8-[3-[4-(4-chlorophenyl)piperidin-1-yl]propoxy]-2-methylsulfonyl-1,3,4,5-tetrahydro-2-benzazepine Chemical compound C1=C2CN(S(=O)(=O)C)CCCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(Cl)C=C1 SCKSYGMBVDCKIZ-UHFFFAOYSA-N 0.000 description 1
AULFGWLEKRXATM-UHFFFAOYSA-N 8-[3-[4-(4-chlorophenyl)piperidin-1-yl]propoxy]-3-cyclopentyl-2,3,4,5-tetrahydro-1h-2-benzazepine Chemical compound C1=CC(Cl)=CC=C1C1CCN(CCCOC=2C=C3CNC(CCC3=CC=2)C2CCCC2)CC1 AULFGWLEKRXATM-UHFFFAOYSA-N 0.000 description 1
CZVWIBVPWIBMHK-UHFFFAOYSA-N 8-[3-[4-(4-chlorophenyl)piperidin-1-yl]propoxy]-3-propan-2-yl-2,3,4,5-tetrahydro-1h-2-benzazepine Chemical compound C1=C2CNC(C(C)C)CCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(Cl)C=C1 CZVWIBVPWIBMHK-UHFFFAOYSA-N 0.000 description 1
OQVIORATQBDUFQ-UHFFFAOYSA-N 8-[3-[4-(4-chlorophenyl)piperidin-1-yl]propoxy]-n-ethyl-1,3,4,5-tetrahydro-2-benzazepine-2-carboxamide Chemical compound C1=C2CN(C(=O)NCC)CCCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(Cl)C=C1 OQVIORATQBDUFQ-UHFFFAOYSA-N 0.000 description 1
PWCXEMKOJIWWNS-UHFFFAOYSA-N 8-[3-[4-(4-fluorophenyl)piperidin-1-yl]propoxy]-2-propan-2-yl-1,3,4,5-tetrahydro-2-benzazepine Chemical compound C1=C2CN(C(C)C)CCCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(F)C=C1 PWCXEMKOJIWWNS-UHFFFAOYSA-N 0.000 description 1
CDDSNGZWHZXFOO-UHFFFAOYSA-N 8-[3-[4-(4-methoxyphenyl)piperidin-1-yl]propoxy]-2-methylsulfonyl-1,3,4,5-tetrahydro-2-benzazepine Chemical compound C1=CC(OC)=CC=C1C1CCN(CCCOC=2C=C3CN(CCCC3=CC=2)S(C)(=O)=O)CC1 CDDSNGZWHZXFOO-UHFFFAOYSA-N 0.000 description 1
ISDFGAPOUVSILO-UHFFFAOYSA-N 8-[3-[4-(4-methoxyphenyl)piperidin-1-yl]propoxy]-2-propan-2-yl-1,3,4,5-tetrahydro-2-benzazepine Chemical compound C1=CC(OC)=CC=C1C1CCN(CCCOC=2C=C3CN(CCCC3=CC=2)C(C)C)CC1 ISDFGAPOUVSILO-UHFFFAOYSA-N 0.000 description 1
ZSFMYBBPPAMDDY-UHFFFAOYSA-N 8-[3-[4-(4-methylphenyl)piperidin-1-yl]propoxy]-2-methylsulfonyl-1,3,4,5-tetrahydro-2-benzazepine Chemical compound C1=CC(C)=CC=C1C1CCN(CCCOC=2C=C3CN(CCCC3=CC=2)S(C)(=O)=O)CC1 ZSFMYBBPPAMDDY-UHFFFAOYSA-N 0.000 description 1
MVPBLTIYSKPNEC-UHFFFAOYSA-N 8-[3-[4-(4-methylphenyl)piperidin-1-yl]propoxy]-2-propan-2-yl-1,3,4,5-tetrahydro-2-benzazepine Chemical compound C1=C2CN(C(C)C)CCCC2=CC=C1OCCCN(CC1)CCC1C1=CC=C(C)C=C1 MVPBLTIYSKPNEC-UHFFFAOYSA-N 0.000 description 1
PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 1
ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 1
208000004611 Abdominal Obesity Diseases 0.000 description 1
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229930024421 Adenine Natural products 0.000 description 1
GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
FHHHOYXPRDYHEZ-COXVUDFISA-N Alacepril Chemical compound CC(=O)SC[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 FHHHOYXPRDYHEZ-COXVUDFISA-N 0.000 description 1
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 1
101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 1
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
XPCFTKFZXHTYIP-PMACEKPBSA-N Benazepril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C2=CC=CC=C2CC1)=O)CC1=CC=CC=C1 XPCFTKFZXHTYIP-PMACEKPBSA-N 0.000 description 1
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
206010004716 Binge eating Diseases 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 description 1
VMIYHDSEFNYJSL-UHFFFAOYSA-N Bromazepam Chemical compound C12=CC(Br)=CC=C2NC(=O)CN=C1C1=CC=CC=N1 VMIYHDSEFNYJSL-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
208000032841 Bulimia Diseases 0.000 description 1
239000002083 C09CA01 - Losartan Substances 0.000 description 1
239000004072 C09CA03 - Valsartan Substances 0.000 description 1
239000002947 C09CA04 - Irbesartan Substances 0.000 description 1
125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 description 1
ZYUZLEUJKZZXNN-UHFFFAOYSA-N C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 Chemical group C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 ZYUZLEUJKZZXNN-UHFFFAOYSA-N 0.000 description 1
SSUFDOMYCBCHML-UHFFFAOYSA-N CCCCC[S](=O)=O Chemical group CCCCC[S](=O)=O SSUFDOMYCBCHML-UHFFFAOYSA-N 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
GHOSNRCGJFBJIB-UHFFFAOYSA-N Candesartan cilexetil Chemical compound C=12N(CC=3C=CC(=CC=3)C=3C(=CC=CC=3)C3=NNN=N3)C(OCC)=NC2=CC=CC=1C(=O)OC(C)OC(=O)OC1CCCCC1 GHOSNRCGJFBJIB-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
241000700198 Cavia Species 0.000 description 1
206010065941 Central obesity Diseases 0.000 description 1
241000282693 Cercopithecidae Species 0.000 description 1
RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 1
101150065749 Churc1 gene Proteins 0.000 description 1
BMOVQUBVGICXQN-UHFFFAOYSA-N Clinofibrate Chemical compound C1=CC(OC(C)(CC)C(O)=O)=CC=C1C1(C=2C=CC(OC(C)(CC)C(O)=O)=CC=2)CCCCC1 BMOVQUBVGICXQN-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
TVZCRIROJQEVOT-CABCVRRESA-N Cromakalim Chemical compound N1([C@@H]2C3=CC(=CC=C3OC([C@H]2O)(C)C)C#N)CCCC1=O TVZCRIROJQEVOT-CABCVRRESA-N 0.000 description 1
229920002785 Croscarmellose sodium Polymers 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-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
102000053602 DNA Human genes 0.000 description 1
239000004287 Dehydroacetic acid Substances 0.000 description 1
FDJCVHVKXFIEPJ-JCNFZFLDSA-N Delapril hydrochloride Chemical compound Cl.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N(CC(O)=O)C1CC2=CC=CC=C2C1)CC1=CC=CC=C1 FDJCVHVKXFIEPJ-JCNFZFLDSA-N 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
208000007342 Diabetic Nephropathies Diseases 0.000 description 1
208000032131 Diabetic Neuropathies Diseases 0.000 description 1
206010012689 Diabetic retinopathy Diseases 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
239000005947 Dimethoate Substances 0.000 description 1
102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
208000030814 Eating disease Diseases 0.000 description 1
108010061435 Enalapril Proteins 0.000 description 1
241000283086 Equidae Species 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
241001302160 Escherichia coli str. K-12 substr. DH10B Species 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
208000019454 Feeding and Eating disease Diseases 0.000 description 1
102100023374 Forkhead box protein M1 Human genes 0.000 description 1
238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
FAEKWTJYAYMJKF-QHCPKHFHSA-N GlucoNorm Chemical compound C1=C(C(O)=O)C(OCC)=CC(CC(=O)N[C@@H](CC(C)C)C=2C(=CC=CC=2)N2CCCCC2)=C1 FAEKWTJYAYMJKF-QHCPKHFHSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
HNSCCNJWTJUGNQ-UHFFFAOYSA-N Glyclopyramide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC(=O)NN1CCCC1 HNSCCNJWTJUGNQ-UHFFFAOYSA-N 0.000 description 1
229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
101000907578 Homo sapiens Forkhead box protein M1 Proteins 0.000 description 1
101000841267 Homo sapiens Long chain 3-hydroxyacyl-CoA dehydrogenase Proteins 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
208000031226 Hyperlipidaemia Diseases 0.000 description 1
206010020710 Hyperphagia Diseases 0.000 description 1
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 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
208000026350 Inborn Genetic disease Diseases 0.000 description 1
AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
229910010082 LiAlH Inorganic materials 0.000 description 1
229940127470 Lipase Inhibitors Drugs 0.000 description 1
229940086609 Lipase inhibitor Drugs 0.000 description 1
SIKWOTFNWURSAY-UHFFFAOYSA-N Lipstatin Natural products CCCCCCC1C(CC(CC=CCC=CCCCCC)C(=O)OC(CC(C)C)NC=O)OC1=O SIKWOTFNWURSAY-UHFFFAOYSA-N 0.000 description 1
108010007859 Lisinopril Proteins 0.000 description 1
102100029107 Long chain 3-hydroxyacyl-CoA dehydrogenase Human genes 0.000 description 1
101150106280 Mchr1 gene Proteins 0.000 description 1
108010047068 Melanin-concentrating hormone receptor Proteins 0.000 description 1
108700036626 Melanin-concentrating hormone receptor 1 Proteins 0.000 description 1
102100027375 Melanin-concentrating hormone receptor 1 Human genes 0.000 description 1
FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical class NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
IBAQFPQHRJAVAV-ULAWRXDQSA-N Miglitol Chemical compound OCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO IBAQFPQHRJAVAV-ULAWRXDQSA-N 0.000 description 1
241001024304 Mino Species 0.000 description 1
PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 1
208000019022 Mood disease Diseases 0.000 description 1
HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
QXJNXHHYWMWUJI-UHFFFAOYSA-N N-[2-[4-(4-chlorophenyl)sulfonyl-2,3-dihydro-1,4-benzoxazin-6-yl]ethyl]-N-propylpropan-1-amine oxalic acid Chemical compound OC(=O)C(O)=O.C12=CC(CCN(CCC)CCC)=CC=C2OCCN1S(=O)(=O)C1=CC=C(Cl)C=C1 QXJNXHHYWMWUJI-UHFFFAOYSA-N 0.000 description 1
206010029333 Neurosis Diseases 0.000 description 1
ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
REMYAXWVMMRUTJ-UHFFFAOYSA-N OC(=O)C(O)=O.C1=CC=CC2=CC(S(=O)(=O)N3CCOC4=CC=C(C=C43)CCCNCCC)=CC=C21 Chemical compound OC(=O)C(O)=O.C1=CC=CC2=CC(S(=O)(=O)N3CCOC4=CC=C(C=C43)CCCNCCC)=CC=C21 REMYAXWVMMRUTJ-UHFFFAOYSA-N 0.000 description 1
IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
UQGKUQLKSCSZGY-UHFFFAOYSA-N Olmesartan medoxomil Chemical compound C=1C=C(C=2C(=CC=CC=2)C2=NNN=N2)C=CC=1CN1C(CCC)=NC(C(C)(C)O)=C1C(=O)OCC=1OC(=O)OC=1C UQGKUQLKSCSZGY-UHFFFAOYSA-N 0.000 description 1
AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
102400000050 Oxytocin Human genes 0.000 description 1
101800000989 Oxytocin Proteins 0.000 description 1
XNOPRXBHLZRZKH-UHFFFAOYSA-N Oxytocin Natural products N1C(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CC(C)C)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C(C(C)CC)NC(=O)C1CC1=CC=C(O)C=C1 XNOPRXBHLZRZKH-UHFFFAOYSA-N 0.000 description 1
AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 description 1
241001494479 Pecora Species 0.000 description 1
208000007683 Pediatric Obesity Diseases 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 1
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 1
102100038239 Protein Churchill Human genes 0.000 description 1
ODHCTXKNWHHXJC-GSVOUGTGSA-N Pyroglutamic acid Natural products OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
241000700159 Rattus Species 0.000 description 1
229940123934 Reductase inhibitor Drugs 0.000 description 1
RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
201000001880 Sexual dysfunction Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
JLRNKCZRCMIVKA-UHFFFAOYSA-N Simfibrate Chemical compound C=1C=C(Cl)C=CC=1OC(C)(C)C(=O)OCCCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 JLRNKCZRCMIVKA-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
241000282887 Suidae Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
201000008736 Systemic mastocytosis Diseases 0.000 description 1
OTFDPNXIVHBTKW-UHFFFAOYSA-N Tiapride hydrochloride Chemical compound [Cl-].CC[NH+](CC)CCNC(=O)C1=CC(S(C)(=O)=O)=CC=C1OC OTFDPNXIVHBTKW-UHFFFAOYSA-N 0.000 description 1
JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
VXFJYXUZANRPDJ-WTNASJBWSA-N Trandopril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@H]2CCCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 VXFJYXUZANRPDJ-WTNASJBWSA-N 0.000 description 1
241000009298 Trigla lyra Species 0.000 description 1
QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Chemical compound CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 description 1
108010004977 Vasopressins Proteins 0.000 description 1
102000002852 Vasopressins Human genes 0.000 description 1
FZNCGRZWXLXZSZ-CIQUZCHMSA-N Voglibose Chemical compound OCC(CO)N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O FZNCGRZWXLXZSZ-CIQUZCHMSA-N 0.000 description 1
NHFMANXEIQVUNZ-UHFFFAOYSA-N [1-[4-(2-methoxyphenyl)piperazin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl] carbamate Chemical compound COC1=CC=CC=C1N1CCN(C(=O)C(OC(N)=O)C(C)(C)C)CC1 NHFMANXEIQVUNZ-UHFFFAOYSA-N 0.000 description 1
YWGIVHDFWPLFCB-UHFFFAOYSA-N [1-[4-(4-fluorophenyl)piperazin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl] carbamate Chemical compound C1CN(C(=O)C(OC(N)=O)C(C)(C)C)CCN1C1=CC=C(F)C=C1 YWGIVHDFWPLFCB-UHFFFAOYSA-N 0.000 description 1
OUULNEJFSDHECE-UHFFFAOYSA-N [4-(4-chlorophenyl)phenyl]-[6-[3-(dimethylamino)-1-hydroxypropyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CCC2=CC(C(O)CCN(C)C)=CC=C2N1C(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1 OUULNEJFSDHECE-UHFFFAOYSA-N 0.000 description 1
TYVXESOHQJWOAX-HWKANZROSA-N [4-(4-chlorophenyl)piperazin-1-yl]-[6-[(e)-3-(dimethylamino)prop-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CCC2=CC(/C=C/CN(C)C)=CC=C2N1C(=O)N(CC1)CCN1C1=CC=C(Cl)C=C1 TYVXESOHQJWOAX-HWKANZROSA-N 0.000 description 1
WMHOLUJEDLCUSW-HWKANZROSA-N [4-(4-chlorophenyl)piperidin-1-yl]-[6-[(e)-3-(dimethylamino)prop-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CCC2=CC(/C=C/CN(C)C)=CC=C2N1C(=O)N(CC1)CCC1C1=CC=C(Cl)C=C1 WMHOLUJEDLCUSW-HWKANZROSA-N 0.000 description 1
APJKKUUDABMFIU-HWKANZROSA-N [4-(4-chlorophenyl)piperidin-1-yl]-[6-[(e)-3-pyrrolidin-1-ylprop-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C1CCN(C(=O)N2C3=CC=C(\C=C\CN4CCCC4)C=C3CCC2)CC1 APJKKUUDABMFIU-HWKANZROSA-N 0.000 description 1
ICZWNHIUIIAHTK-HWKANZROSA-N [4-(4-fluorophenyl)piperidin-1-yl]-[6-[(e)-3-pyrrolidin-1-ylprop-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C1CCN(C(=O)N2C3=CC=C(\C=C\CN4CCCC4)C=C3CCC2)CC1 ICZWNHIUIIAHTK-HWKANZROSA-N 0.000 description 1
YHXIXBLNCLGACP-GQCTYLIASA-N [4-(4-methylphenyl)piperidin-1-yl]-[6-[(e)-3-pyrrolidin-1-ylprop-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(C)=CC=C1C1CCN(C(=O)N2C3=CC=C(\C=C\CN4CCCC4)C=C3CCC2)CC1 YHXIXBLNCLGACP-GQCTYLIASA-N 0.000 description 1
IIMDMIVFENRBQK-ONEGZZNKSA-N [4-[(4-chlorophenyl)methoxy]phenyl]-[5-[(e)-3-(dimethylamino)prop-1-enyl]-2,3-dihydroindol-1-yl]methanone Chemical compound C1CC2=CC(/C=C/CN(C)C)=CC=C2N1C(=O)C(C=C1)=CC=C1OCC1=CC=C(Cl)C=C1 IIMDMIVFENRBQK-ONEGZZNKSA-N 0.000 description 1
QOXNTOUGOYCRDK-HWKANZROSA-N [5-(4-fluorophenyl)pyridin-2-yl]-[6-[(e)-3-pyrrolidin-1-ylprop-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C1=CC=C(C(=O)N2C3=CC=C(\C=C\CN4CCCC4)C=C3CCC2)N=C1 QOXNTOUGOYCRDK-HWKANZROSA-N 0.000 description 1
YMHQEEGBMMNKCH-GQCTYLIASA-N [5-(4-methylphenyl)pyridin-2-yl]-[6-[(e)-3-pyrrolidin-1-ylprop-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(C)=CC=C1C1=CC=C(C(=O)N2C3=CC=C(\C=C\CN4CCCC4)C=C3CCC2)N=C1 YMHQEEGBMMNKCH-GQCTYLIASA-N 0.000 description 1
IKLPRHXKOOSRFL-SNAWJCMRSA-N [5-[(e)-3-(dimethylamino)prop-1-enyl]-2,3-dihydroindol-1-yl]-[4-[(4-methylphenyl)methoxy]phenyl]methanone Chemical compound C1CC2=CC(/C=C/CN(C)C)=CC=C2N1C(=O)C(C=C1)=CC=C1OCC1=CC=C(C)C=C1 IKLPRHXKOOSRFL-SNAWJCMRSA-N 0.000 description 1
OBIYJVKXHMFFCL-HWKANZROSA-N [6-(4-chlorophenyl)pyridin-3-yl]-[6-[(e)-3-(dimethylamino)prop-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CCC2=CC(/C=C/CN(C)C)=CC=C2N1C(=O)C(C=N1)=CC=C1C1=CC=C(Cl)C=C1 OBIYJVKXHMFFCL-HWKANZROSA-N 0.000 description 1
JGUPMUZXBYTMLC-HWKANZROSA-N [6-(4-chlorophenyl)pyridin-3-yl]-[6-[(e)-3-pyrrolidin-1-ylprop-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(C(=O)N2C3=CC=C(\C=C\CN4CCCC4)C=C3CCC2)C=N1 JGUPMUZXBYTMLC-HWKANZROSA-N 0.000 description 1
MBKQRWFFKDRORV-ZZXKWVIFSA-N [6-(4-chlorophenyl)pyridin-3-yl]-[6-[(e)-4-(dimethylamino)but-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CCC2=CC(/C=C/CCN(C)C)=CC=C2N1C(=O)C(C=N1)=CC=C1C1=CC=C(Cl)C=C1 MBKQRWFFKDRORV-ZZXKWVIFSA-N 0.000 description 1
VNUUDAGADNNXQH-LZCJLJQNSA-N [6-(4-chlorophenyl)pyridin-3-yl]-[6-[(e)-4-pyrrolidin-1-ylbut-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(C(=O)N2C3=CC=C(\C=C\CCN4CCCC4)C=C3CCC2)C=N1 VNUUDAGADNNXQH-LZCJLJQNSA-N 0.000 description 1
XELYTHNBKIEWDU-HWKANZROSA-N [6-(4-fluorophenyl)pyridin-3-yl]-[6-[(e)-3-pyrrolidin-1-ylprop-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C1=CC=C(C(=O)N2C3=CC=C(\C=C\CN4CCCC4)C=C3CCC2)C=N1 XELYTHNBKIEWDU-HWKANZROSA-N 0.000 description 1
ZDPOHBFIMRHYOT-LZCJLJQNSA-N [6-(4-fluorophenyl)pyridin-3-yl]-[6-[(e)-4-pyrrolidin-1-ylbut-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C1=CC=C(C(=O)N2C3=CC=C(\C=C\CCN4CCCC4)C=C3CCC2)C=N1 ZDPOHBFIMRHYOT-LZCJLJQNSA-N 0.000 description 1
UZBOWWKVGWBJBQ-GQCTYLIASA-N [6-(4-methylphenyl)pyridin-3-yl]-[6-[(e)-3-pyrrolidin-1-ylprop-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(C)=CC=C1C1=CC=C(C(=O)N2C3=CC=C(\C=C\CN4CCCC4)C=C3CCC2)C=N1 UZBOWWKVGWBJBQ-GQCTYLIASA-N 0.000 description 1
CVVGZFXZMJDXPF-FARCUNLSSA-N [6-(4-methylphenyl)pyridin-3-yl]-[6-[(e)-4-pyrrolidin-1-ylbut-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(C)=CC=C1C1=CC=C(C(=O)N2C3=CC=C(\C=C\CCN4CCCC4)C=C3CCC2)C=N1 CVVGZFXZMJDXPF-FARCUNLSSA-N 0.000 description 1
KGFGDJNCSTWQAO-HWKANZROSA-N [6-[(e)-3-(dimethylamino)prop-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]-[4-(4-fluorophenyl)piperazin-1-yl]methanone Chemical compound C1CCC2=CC(/C=C/CN(C)C)=CC=C2N1C(=O)N(CC1)CCN1C1=CC=C(F)C=C1 KGFGDJNCSTWQAO-HWKANZROSA-N 0.000 description 1
NRACFKXRKVCPAD-HWKANZROSA-N [6-[(e)-3-(dimethylamino)prop-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]-[4-(4-fluorophenyl)piperidin-1-yl]methanone Chemical compound C1CCC2=CC(/C=C/CN(C)C)=CC=C2N1C(=O)N(CC1)CCC1C1=CC=C(F)C=C1 NRACFKXRKVCPAD-HWKANZROSA-N 0.000 description 1
BLHOLVCDMRHQGR-GQCTYLIASA-N [6-[(e)-3-(dimethylamino)prop-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]-[4-(4-methylphenyl)piperazin-1-yl]methanone Chemical compound C1CCC2=CC(/C=C/CN(C)C)=CC=C2N1C(=O)N(CC1)CCN1C1=CC=C(C)C=C1 BLHOLVCDMRHQGR-GQCTYLIASA-N 0.000 description 1
FVIBWNJCQJWWCY-GQCTYLIASA-N [6-[(e)-3-(dimethylamino)prop-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]-[4-(4-methylphenyl)piperidin-1-yl]methanone Chemical compound C1CCC2=CC(/C=C/CN(C)C)=CC=C2N1C(=O)N(CC1)CCC1C1=CC=C(C)C=C1 FVIBWNJCQJWWCY-GQCTYLIASA-N 0.000 description 1
SQUNRDNNEWLZKH-HWKANZROSA-N [6-[(e)-3-(dimethylamino)prop-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]-[6-(4-fluorophenyl)pyridin-3-yl]methanone Chemical compound C1CCC2=CC(/C=C/CN(C)C)=CC=C2N1C(=O)C(C=N1)=CC=C1C1=CC=C(F)C=C1 SQUNRDNNEWLZKH-HWKANZROSA-N 0.000 description 1
GAZTZPKDWRNADT-GQCTYLIASA-N [6-[(e)-3-(dimethylamino)prop-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]-[6-(4-methylphenyl)pyridin-3-yl]methanone Chemical compound C1CCC2=CC(/C=C/CN(C)C)=CC=C2N1C(=O)C(C=N1)=CC=C1C1=CC=C(C)C=C1 GAZTZPKDWRNADT-GQCTYLIASA-N 0.000 description 1
HJNPCFRIMHWSEG-ZZXKWVIFSA-N [6-[(e)-4-(dimethylamino)but-1-enyl]-3,4-dihydro-2h-quinolin-1-yl]-[6-(4-fluorophenyl)pyridin-3-yl]methanone Chemical compound C1CCC2=CC(/C=C/CCN(C)C)=CC=C2N1C(=O)C(C=N1)=CC=C1C1=CC=C(F)C=C1 HJNPCFRIMHWSEG-ZZXKWVIFSA-N 0.000 description 1
RWNWOIGDDMPZRG-UHFFFAOYSA-N [6-[2-(dipropylamino)ethyl]-2,3-dihydro-1,4-benzoxazin-4-yl]-naphthalen-2-ylmethanone;hydrochloride Chemical compound Cl.C1=CC=CC2=CC(C(=O)N3CCOC4=CC=C(C=C43)CCN(CCC)CCC)=CC=C21 RWNWOIGDDMPZRG-UHFFFAOYSA-N 0.000 description 1
LEVKKZKUBVUNQB-UHFFFAOYSA-N [6-[3-(dimethylamino)propyl]-3,4-dihydro-2h-quinolin-1-yl]-(4-phenylphenyl)methanone Chemical compound C1CCC2=CC(CCCN(C)C)=CC=C2N1C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 LEVKKZKUBVUNQB-UHFFFAOYSA-N 0.000 description 1
CWQBIOOJOGNXBC-UHFFFAOYSA-N [7-[2-(dimethylamino)ethoxy]-6-methoxy-3,4-dihydro-2h-quinolin-1-yl]-[4-[2-methyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methanone Chemical compound C1=2C=C(OCCN(C)C)C(OC)=CC=2CCCN1C(=O)C(C=C1)=CC=C1C(C(=C1)C)=CC=C1C1=NOC(C)=N1 CWQBIOOJOGNXBC-UHFFFAOYSA-N 0.000 description 1
BUSSFZKUJHXAKO-UHFFFAOYSA-N [7-[3-(dimethylamino)propyl]-6-methoxy-3,4-dihydro-2h-quinolin-1-yl]-[4-[2-methyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methanone Chemical compound C1=2C=C(CCCN(C)C)C(OC)=CC=2CCCN1C(=O)C(C=C1)=CC=C1C(C(=C1)C)=CC=C1C1=NOC(C)=N1 BUSSFZKUJHXAKO-UHFFFAOYSA-N 0.000 description 1
OWJNLZMOWBGLIG-UHFFFAOYSA-N [7-[3-[4-(4-chlorophenyl)piperidin-1-yl]propoxy]-1,2,4,5-tetrahydro-3-benzazepin-3-yl]-phenylmethanone Chemical compound C1=CC(Cl)=CC=C1C1CCN(CCCOC=2C=C3CCN(CCC3=CC=2)C(=O)C=2C=CC=CC=2)CC1 OWJNLZMOWBGLIG-UHFFFAOYSA-N 0.000 description 1
GWAFENKWUCCPSQ-HRNDJLQDSA-N [8-[(e)-3-(dimethylamino)prop-1-enyl]-2,3,4,5-tetrahydro-1-benzazepin-1-yl]-(4-phenylphenyl)methanone;hydrochloride Chemical compound Cl.C12=CC(/C=C/CN(C)C)=CC=C2CCCCN1C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 GWAFENKWUCCPSQ-HRNDJLQDSA-N 0.000 description 1
RFGPNLBLDYFOOU-UHFFFAOYSA-N [8-[3-(dimethylamino)propyl]-2,3,4,5-tetrahydro-1-benzazepin-1-yl]-(4-phenylphenyl)methanone;hydrochloride Chemical compound Cl.C12=CC(CCCN(C)C)=CC=C2CCCCN1C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 RFGPNLBLDYFOOU-UHFFFAOYSA-N 0.000 description 1
ZUXHQSJVYVCHOE-UHFFFAOYSA-N [8-[3-[4-(4-chlorophenyl)piperidin-1-yl]propoxy]-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-phenylmethanone Chemical compound C1=CC(Cl)=CC=C1C1CCN(CCCOC=2C=C3CN(CCCC3=CC=2)C(=O)C=2C=CC=CC=2)CC1 ZUXHQSJVYVCHOE-UHFFFAOYSA-N 0.000 description 1
230000005856 abnormality Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
229960002632 acarbose Drugs 0.000 description 1
XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
PAAZCQANMCYGAW-UHFFFAOYSA-N acetic acid;2,2,2-trifluoroacetic acid Chemical compound CC(O)=O.OC(=O)C(F)(F)F PAAZCQANMCYGAW-UHFFFAOYSA-N 0.000 description 1
229960001466 acetohexamide Drugs 0.000 description 1
VGZSUPCWNCWDAN-UHFFFAOYSA-N acetohexamide Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 VGZSUPCWNCWDAN-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
239000012190 activator Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
229960000643 adenine Drugs 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
229950007884 alacepril Drugs 0.000 description 1
MKOMESMZHZNBIZ-UHFFFAOYSA-M alagebrium Chemical compound [Cl-].CC1=C(C)SC=[N+]1CC(=O)C1=CC=CC=C1 MKOMESMZHZNBIZ-UHFFFAOYSA-M 0.000 description 1
235000004279 alanine Nutrition 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000004450 alkenylene group Chemical group 0.000 description 1
125000003302 alkenyloxy group Chemical group 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000004448 alkyl carbonyl group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229960004538 alprazolam Drugs 0.000 description 1
VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 1
229960000711 alprostadil Drugs 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
125000000539 amino acid group Chemical group 0.000 description 1
HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 1
HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 description 1
229960000528 amlodipine Drugs 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
229940125713 antianxiety drug Drugs 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
230000000949 anxiolytic effect Effects 0.000 description 1
229940005530 anxiolytics Drugs 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 1
125000004657 aryl sulfonyl amino group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
235000009582 asparagine Nutrition 0.000 description 1
229960001230 asparagine Drugs 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
229960005370 atorvastatin Drugs 0.000 description 1
150000001537 azepanes Chemical class 0.000 description 1
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
230000006399 behavior Effects 0.000 description 1
229960004530 benazepril Drugs 0.000 description 1
229960000686 benzalkonium chloride Drugs 0.000 description 1
UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 1
229960001950 benzethonium chloride Drugs 0.000 description 1
MXMZCLLIUQEKSN-UHFFFAOYSA-N benzimidazoline Chemical compound C1=CC=C2NCNC2=C1 MXMZCLLIUQEKSN-UHFFFAOYSA-N 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
229960002903 benzyl benzoate Drugs 0.000 description 1
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
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
229960000516 bezafibrate Drugs 0.000 description 1
IIBYAHWJQTYFKB-UHFFFAOYSA-N bezafibrate Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1 IIBYAHWJQTYFKB-UHFFFAOYSA-N 0.000 description 1
208000014679 binge eating disease Diseases 0.000 description 1
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 1
230000037396 body weight Effects 0.000 description 1
229910000085 borane Inorganic materials 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
229960002729 bromazepam Drugs 0.000 description 1
IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 1
OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 1
RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 1
RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 1
229960004111 buformin Drugs 0.000 description 1
XSEUMFJMFFMCIU-UHFFFAOYSA-N buformin Chemical compound CCCC\N=C(/N)N=C(N)N XSEUMFJMFFMCIU-UHFFFAOYSA-N 0.000 description 1
244000309464 bull Species 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
229910000024 caesium carbonate Inorganic materials 0.000 description 1
239000000480 calcium channel blocker Substances 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
LEMUFSYUPGXXCM-JNEQYSBXSA-N caninsulin Chemical compound [Zn].C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC3N=CN=C3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)O)C(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1C=NC=N1 LEMUFSYUPGXXCM-JNEQYSBXSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229960000830 captopril Drugs 0.000 description 1
FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
229940105329 carboxymethylcellulose Drugs 0.000 description 1
229940084030 carboxymethylcellulose calcium Drugs 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
229960005110 cerivastatin Drugs 0.000 description 1
SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 description 1
230000008859 change Effects 0.000 description 1
238000000451 chemical ionisation Methods 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
229960004782 chlordiazepoxide Drugs 0.000 description 1
229960004926 chlorobutanol Drugs 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
229960001761 chlorpropamide Drugs 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
HHHKFGXWKKUNCY-FHWLQOOXSA-N cilazapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N2[C@@H](CCCN2CCC1)C(O)=O)=O)CC1=CC=CC=C1 HHHKFGXWKKUNCY-FHWLQOOXSA-N 0.000 description 1
229960005025 cilazapril Drugs 0.000 description 1
RRGUKTPIGVIEKM-UHFFFAOYSA-N cilostazol Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCC1=NN=NN1C1CCCCC1 RRGUKTPIGVIEKM-UHFFFAOYSA-N 0.000 description 1
229960004588 cilostazol Drugs 0.000 description 1
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
229950003072 clinofibrate Drugs 0.000 description 1
229960001214 clofibrate Drugs 0.000 description 1
KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 1
ZIXNZOBDFKSQTC-UHFFFAOYSA-N cloxazolam Chemical compound C12=CC(Cl)=CC=C2NC(=O)CN2CCOC21C1=CC=CC=C1Cl ZIXNZOBDFKSQTC-UHFFFAOYSA-N 0.000 description 1
229960003932 cloxazolam Drugs 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
238000007796 conventional method Methods 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
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
229960001681 croscarmellose sodium Drugs 0.000 description 1
235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
150000001924 cycloalkanes Chemical class 0.000 description 1
125000002993 cycloalkylene group Chemical group 0.000 description 1
125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
DZFSTAUMUPHORN-NRFANRHFSA-N cyclohexyl-[[4-[2-[[(2s)-2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]phenoxy]methyl]phosphinic acid Chemical compound C([C@H](O)COC=1C=CC(O)=CC=1)NCCC(C=C1)=CC=C1OCP(O)(=O)C1CCCCC1 DZFSTAUMUPHORN-NRFANRHFSA-N 0.000 description 1
125000004956 cyclohexylene group Chemical group 0.000 description 1
125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
229940104302 cytosine Drugs 0.000 description 1
SUYVUBYJARFZHO-UHFFFAOYSA-N dATP Natural products C1=NC=2C(N)=NC=NC=2N1C1CC(O)C(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1 SUYVUBYJARFZHO-UHFFFAOYSA-N 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
235000019258 dehydroacetic acid Nutrition 0.000 description 1
229940061632 dehydroacetic acid Drugs 0.000 description 1
239000003405 delayed action preparation Substances 0.000 description 1
238000013461 design Methods 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
208000033679 diabetic kidney disease Diseases 0.000 description 1
229960003529 diazepam Drugs 0.000 description 1
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
230000000378 dietary effect Effects 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
235000014632 disordered eating Nutrition 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
235000005686 eating Nutrition 0.000 description 1
230000020595 eating behavior Effects 0.000 description 1
229950003102 efonidipine Drugs 0.000 description 1
229950000269 emiglitate Drugs 0.000 description 1
229960000873 enalapril Drugs 0.000 description 1
GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
CHNUOJQWGUIOLD-NFZZJPOKSA-N epalrestat Chemical compound C=1C=CC=CC=1\C=C(/C)\C=C1/SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-NFZZJPOKSA-N 0.000 description 1
229950010170 epalrestat Drugs 0.000 description 1
CHNUOJQWGUIOLD-UHFFFAOYSA-N epalrestate Natural products C=1C=CC=CC=1C=C(C)C=C1SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-UHFFFAOYSA-N 0.000 description 1
229940023064 escherichia coli Drugs 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
SSQPWTVBQMWLSZ-AAQCHOMXSA-N ethyl (5Z,8Z,11Z,14Z,17Z)-icosapentaenoate Chemical compound CCOC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC SSQPWTVBQMWLSZ-AAQCHOMXSA-N 0.000 description 1
NWWORXYTJRPSMC-QKPAOTATSA-N ethyl 4-[2-[(2r,3r,4r,5s)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]ethoxy]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1OCCN1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)C1 NWWORXYTJRPSMC-QKPAOTATSA-N 0.000 description 1
YIBTVFIOOJILFJ-UHFFFAOYSA-N ethyl 6-(3-chloropropanoyl)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound ClCCC(=O)C1=CC=C2N(C(=O)OCC)CCCC2=C1 YIBTVFIOOJILFJ-UHFFFAOYSA-N 0.000 description 1
MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
238000009207 exercise therapy Methods 0.000 description 1
230000004634 feeding behavior Effects 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 1
239000007941 film coated tablet Substances 0.000 description 1
229960004930 fludiazepam Drugs 0.000 description 1
ROYOYTLGDLIGBX-UHFFFAOYSA-N fludiazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F ROYOYTLGDLIGBX-UHFFFAOYSA-N 0.000 description 1
RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
229960003765 fluvastatin Drugs 0.000 description 1
229960004038 fluvoxamine Drugs 0.000 description 1
CJOFXWAVKWHTFT-XSFVSMFZSA-N fluvoxamine Chemical compound COCCCC\C(=N/OCCN)C1=CC=C(C(F)(F)F)C=C1 CJOFXWAVKWHTFT-XSFVSMFZSA-N 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
229940013688 formic acid Drugs 0.000 description 1
239000012634 fragment Substances 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
208000016361 genetic disease Diseases 0.000 description 1
230000002068 genetic effect Effects 0.000 description 1
238000010353 genetic engineering Methods 0.000 description 1
229960004580 glibenclamide Drugs 0.000 description 1
229960000346 gliclazide Drugs 0.000 description 1
229960004346 glimepiride Drugs 0.000 description 1
WIGIZIANZCJQQY-RUCARUNLSA-N glimepiride Chemical compound O=C1C(CC)=C(C)CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N[C@@H]2CC[C@@H](C)CC2)C=C1 WIGIZIANZCJQQY-RUCARUNLSA-N 0.000 description 1
239000008103 glucose Substances 0.000 description 1
229930195712 glutamate Natural products 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
229950002888 glyclopyramide Drugs 0.000 description 1
QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
UPZJLQCUYUTZIE-UHFFFAOYSA-N hydron;4-phenylpiperidine;chloride Chemical compound Cl.C1CNCCC1C1=CC=CC=C1 UPZJLQCUYUTZIE-UHFFFAOYSA-N 0.000 description 1
229920001477 hydrophilic polymer Polymers 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
229940071676 hydroxypropylcellulose Drugs 0.000 description 1
239000005555 hypertensive agent Substances 0.000 description 1
230000002267 hypothalamic effect Effects 0.000 description 1
210000003016 hypothalamus Anatomy 0.000 description 1
229960001680 ibuprofen Drugs 0.000 description 1
229960002600 icosapent ethyl Drugs 0.000 description 1
229960001195 imidapril Drugs 0.000 description 1
KLZWOWYOHUKJIG-BPUTZDHNSA-N imidapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1C(N(C)C[C@H]1C(O)=O)=O)CC1=CC=CC=C1 KLZWOWYOHUKJIG-BPUTZDHNSA-N 0.000 description 1
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
229960004801 imipramine Drugs 0.000 description 1
229950007327 imirestat Drugs 0.000 description 1
238000003018 immunoassay Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
238000000752 ionisation method Methods 0.000 description 1
229960002198 irbesartan Drugs 0.000 description 1
YCPOHTHPUREGFM-UHFFFAOYSA-N irbesartan Chemical compound O=C1N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2[N]N=NN=2)C(CCCC)=NC21CCCC2 YCPOHTHPUREGFM-UHFFFAOYSA-N 0.000 description 1
GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
239000007951 isotonicity adjuster Substances 0.000 description 1
210000003127 knee Anatomy 0.000 description 1
238000011813 knockout mouse model Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
OQMAKWGYQLJJIA-CUOOPAIESA-N lipstatin Chemical compound CCCCCC[C@H]1[C@H](C[C@H](C\C=C/C\C=C/CCCCC)OC(=O)[C@H](CC(C)C)NC=O)OC1=O OQMAKWGYQLJJIA-CUOOPAIESA-N 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
229960002394 lisinopril Drugs 0.000 description 1
CZRQXSDBMCMPNJ-ZUIPZQNBSA-N lisinopril dihydrate Chemical compound O.O.C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 CZRQXSDBMCMPNJ-ZUIPZQNBSA-N 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
229960004391 lorazepam Drugs 0.000 description 1
229960004773 losartan Drugs 0.000 description 1
KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 description 1
229960004844 lovastatin Drugs 0.000 description 1
PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 1
QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
229960003511 macrogol Drugs 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
ANEBWFXPVPTEET-UHFFFAOYSA-N manidipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN2CCN(CC2)C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ANEBWFXPVPTEET-UHFFFAOYSA-N 0.000 description 1
229960003963 manidipine Drugs 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
208000008585 mastocytosis Diseases 0.000 description 1
239000000463 material Substances 0.000 description 1
229960002225 medazepam Drugs 0.000 description 1
102000006953 melanin-concentrating hormone receptor activity proteins Human genes 0.000 description 1
BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 description 1
229960004640 memantine Drugs 0.000 description 1
AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 1
XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
229960003105 metformin Drugs 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
WVJKHCGMRZGIJH-UHFFFAOYSA-N methanetriamine Chemical compound NC(N)N WVJKHCGMRZGIJH-UHFFFAOYSA-N 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
238000006063 methoxycarbonylation reaction Methods 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
229960002900 methylcellulose Drugs 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
SOHCYNFHNYKSTM-UHFFFAOYSA-N methylsulfinylmethane;oxolane Chemical class CS(C)=O.C1CCOC1 SOHCYNFHNYKSTM-UHFFFAOYSA-N 0.000 description 1
VLPIATFUUWWMKC-UHFFFAOYSA-N mexiletine Chemical compound CC(N)COC1=C(C)C=CC=C1C VLPIATFUUWWMKC-UHFFFAOYSA-N 0.000 description 1
229960001070 mexiletine hydrochloride Drugs 0.000 description 1
239000003094 microcapsule Substances 0.000 description 1
229960001110 miglitol Drugs 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
229960003365 mitiglinide Drugs 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 1
ACTNHJDHMQSOGL-UHFFFAOYSA-N n',n'-dibenzylethane-1,2-diamine Chemical compound C=1C=CC=CC=1CN(CCN)CC1=CC=CC=C1 ACTNHJDHMQSOGL-UHFFFAOYSA-N 0.000 description 1
CZFNISFYDPIDNM-UHFFFAOYSA-N n,n-dimethylformamide;oxolane Chemical compound CN(C)C=O.C1CCOC1 CZFNISFYDPIDNM-UHFFFAOYSA-N 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
HBOMNFSZMMXJME-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-4-oxo-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C1CNCCC2=CC(C(=O)CCC(=O)NCC=3C=C4OCOC4=CC=3)=CC=C21 HBOMNFSZMMXJME-UHFFFAOYSA-N 0.000 description 1
IXPNAPICBSZZIC-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-4-oxo-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)NC(CC1)CCN1CC1=CC=CC=C1 IXPNAPICBSZZIC-UHFFFAOYSA-N 0.000 description 1
ROANDDZZWQPARM-UHFFFAOYSA-N n-(1-benzylpyrrolidin-3-yl)-4-oxo-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)NC(C1)CCN1CC1=CC=CC=C1 ROANDDZZWQPARM-UHFFFAOYSA-N 0.000 description 1
AJPQDCDVRWKCBX-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-4-oxo-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C1CNCCC2=CC(C(=O)CCC(=O)NC3CC4=CC=CC=C4C3)=CC=C21 AJPQDCDVRWKCBX-UHFFFAOYSA-N 0.000 description 1
AGRSYKDSEWRXBS-UHFFFAOYSA-N n-(2-anilinoethyl)-4-oxo-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)NCCNC1=CC=CC=C1 AGRSYKDSEWRXBS-UHFFFAOYSA-N 0.000 description 1
GGQIAERQKHVVCA-UHFFFAOYSA-N n-(2-morpholin-4-ylethyl)-4-oxo-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)NCCN1CCOCC1 GGQIAERQKHVVCA-UHFFFAOYSA-N 0.000 description 1
ZBFRCAHQRVGQAB-UHFFFAOYSA-N n-(3,3-diphenylpropyl)-4-oxo-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)NCCC(C=1C=CC=CC=1)C1=CC=CC=C1 ZBFRCAHQRVGQAB-UHFFFAOYSA-N 0.000 description 1
OAHQBWWXUMUYIR-UHFFFAOYSA-N n-(3-morpholin-4-ylpropyl)-4-oxo-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)NCCCN1CCOCC1 OAHQBWWXUMUYIR-UHFFFAOYSA-N 0.000 description 1
KFTYNYHJHKCRKU-UHFFFAOYSA-N n-(3-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC([N+]([O-])=O)=C1 KFTYNYHJHKCRKU-UHFFFAOYSA-N 0.000 description 1
RGQXWNSJEUGMND-UHFFFAOYSA-N n-(cyclohexylmethyl)-4-oxo-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)NCC1CCCCC1 RGQXWNSJEUGMND-UHFFFAOYSA-N 0.000 description 1
LUQZFLSXNIZZNZ-UHFFFAOYSA-N n-[1-[4-oxo-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanoyl]pyrrolidin-3-yl]acetamide Chemical compound C1C(NC(=O)C)CCN1C(=O)CCC(=O)C1=CC=C(CCNCC2)C2=C1 LUQZFLSXNIZZNZ-UHFFFAOYSA-N 0.000 description 1
UAWPPYNKDANBRD-UHFFFAOYSA-N n-[2-(1h-indol-3-yl)ethyl]-4-oxo-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C1CNCCC2=CC(C(=O)CCC(=O)NCCC=3C4=CC=CC=C4NC=3)=CC=C21 UAWPPYNKDANBRD-UHFFFAOYSA-N 0.000 description 1
OVGCWIODCUGRIO-UHFFFAOYSA-N n-[2-[3-(4-methoxyphenyl)-3,4-dihydro-2h-1,4-benzoxazin-6-yl]ethyl]-n-propylpropan-1-amine;hydrochloride Chemical compound Cl.N1C2=CC(CCN(CCC)CCC)=CC=C2OCC1C1=CC=C(OC)C=C1 OVGCWIODCUGRIO-UHFFFAOYSA-N 0.000 description 1
BCJFFZPSSKJLCM-UHFFFAOYSA-N n-[2-[4-(2-methoxyphenyl)piperazin-1-yl]-2-oxoethyl]-2,3,4,5-tetrahydro-1h-2-benzazepine-8-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC=C1N1CCN(C(=O)CNC(=O)C=2C=C3CNCCCC3=CC=2)CC1 BCJFFZPSSKJLCM-UHFFFAOYSA-N 0.000 description 1
BPFOMYSZWJIUBN-UHFFFAOYSA-N n-[2-[4-(2-methoxyphenyl)piperazin-1-yl]-2-oxoethyl]-2,3,4,5-tetrahydro-1h-3-benzazepine-7-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC=C1N1CCN(C(=O)CNC(=O)C=2C=C3CCNCCC3=CC=2)CC1 BPFOMYSZWJIUBN-UHFFFAOYSA-N 0.000 description 1
REGSRKWZRDDYCU-UHFFFAOYSA-N n-[2-[4-(2-methylphenyl)piperidin-1-yl]-2-oxoethyl]-2,3,4,5-tetrahydro-1h-2-benzazepine-8-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC=CC=C1C1CCN(C(=O)CNC(=O)C=2C=C3CNCCCC3=CC=2)CC1 REGSRKWZRDDYCU-UHFFFAOYSA-N 0.000 description 1
PAKSFPJFMFKRGW-UHFFFAOYSA-N n-[2-[4-(2-methylphenyl)piperidin-1-yl]-2-oxoethyl]-2,3,4,5-tetrahydro-1h-3-benzazepine-7-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC=CC=C1C1CCN(C(=O)CNC(=O)C=2C=C3CCNCCC3=CC=2)CC1 PAKSFPJFMFKRGW-UHFFFAOYSA-N 0.000 description 1
ZFNZXWMVEAMVBM-UHFFFAOYSA-N n-[2-[4-(4-chlorophenyl)piperidin-1-yl]-2-oxoethyl]-2,3,4,5-tetrahydro-1h-2-benzazepine-8-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(Cl)=CC=C1C1CCN(C(=O)CNC(=O)C=2C=C3CNCCCC3=CC=2)CC1 ZFNZXWMVEAMVBM-UHFFFAOYSA-N 0.000 description 1
GRQGVZAQJGOOSU-UHFFFAOYSA-N n-[2-[4-(4-chlorophenyl)piperidin-1-yl]-2-oxoethyl]-2,3,4,5-tetrahydro-1h-3-benzazepine-7-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(Cl)=CC=C1C1CCN(C(=O)CNC(=O)C=2C=C3CCNCCC3=CC=2)CC1 GRQGVZAQJGOOSU-UHFFFAOYSA-N 0.000 description 1
LLJHEZLDBQOBOK-UHFFFAOYSA-N n-[2-[4-(4-fluorophenyl)piperazin-1-yl]-2-oxoethyl]-2,3,4,5-tetrahydro-1h-2-benzazepine-8-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(F)=CC=C1N1CCN(C(=O)CNC(=O)C=2C=C3CNCCCC3=CC=2)CC1 LLJHEZLDBQOBOK-UHFFFAOYSA-N 0.000 description 1
ASXJHOZNHPRIOB-UHFFFAOYSA-N n-[2-[4-(4-fluorophenyl)piperazin-1-yl]-2-oxoethyl]-2,3,4,5-tetrahydro-1h-3-benzazepine-7-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(F)=CC=C1N1CCN(C(=O)CNC(=O)C=2C=C3CCNCCC3=CC=2)CC1 ASXJHOZNHPRIOB-UHFFFAOYSA-N 0.000 description 1
RBXNOTFIWSYLFF-UHFFFAOYSA-N n-[2-[4-(naphthalen-1-ylmethyl)-2,3-dihydro-1,4-benzoxazin-6-yl]ethyl]-n-propylpropan-1-amine;hydrochloride Chemical compound Cl.C1=CC=C2C(CN3CCOC4=CC=C(C=C43)CCN(CCC)CCC)=CC=CC2=C1 RBXNOTFIWSYLFF-UHFFFAOYSA-N 0.000 description 1
VSNFSXDTPOARDY-UHFFFAOYSA-N n-[2-[4-(naphthalen-2-ylmethyl)-2,3-dihydro-1,4-benzoxazin-6-yl]ethyl]-n-propylpropan-1-amine;hydrochloride Chemical compound Cl.C1=CC=CC2=CC(CN3CCOC4=CC=C(C=C43)CCN(CCC)CCC)=CC=C21 VSNFSXDTPOARDY-UHFFFAOYSA-N 0.000 description 1
ISWYPWVINLRXGH-UHFFFAOYSA-N n-[3-(4-chlorophenyl)propyl]-4-oxo-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C1=CC(Cl)=CC=C1CCCNC(=O)CCC(=O)C1=CC=C(CCNCC2)C2=C1 ISWYPWVINLRXGH-UHFFFAOYSA-N 0.000 description 1
KDGMUHMWPKKMFB-UHFFFAOYSA-N n-[4-[7-[3-(dimethylamino)propoxy]-2,3,4,5-tetrahydro-1-benzazepine-1-carbonyl]phenyl]-2-methylbenzamide Chemical compound C1CCCC2=CC(OCCCN(C)C)=CC=C2N1C(=O)C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C KDGMUHMWPKKMFB-UHFFFAOYSA-N 0.000 description 1
BNNYPKRZHKTAFG-UHFFFAOYSA-N n-benzhydryl-4-oxo-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)NC(C=1C=CC=CC=1)C1=CC=CC=C1 BNNYPKRZHKTAFG-UHFFFAOYSA-N 0.000 description 1
XNDQSXPWQVMLPL-UHFFFAOYSA-N n-butyl-4-oxo-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C1CNCCC2=CC(C(=O)CCC(=O)NCCCC)=CC=C21 XNDQSXPWQVMLPL-UHFFFAOYSA-N 0.000 description 1
XVZZXRZYKWOQIO-UHFFFAOYSA-N n-cyclopropyl-4-oxo-4-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)butanamide Chemical compound C=1C=C2CCNCCC2=CC=1C(=O)CCC(=O)NC1CC1 XVZZXRZYKWOQIO-UHFFFAOYSA-N 0.000 description 1
ZUSSTQCWRDLYJA-UHFFFAOYSA-N n-hydroxy-5-norbornene-2,3-dicarboximide Chemical compound C1=CC2CC1C1C2C(=O)N(O)C1=O ZUSSTQCWRDLYJA-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
DASJFYAPNPUBGG-UHFFFAOYSA-N naphthalene-1-sulfonyl chloride Chemical compound C1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=C1 DASJFYAPNPUBGG-UHFFFAOYSA-N 0.000 description 1
OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 1
OELFLUMRDSZNSF-BRWVUGGUSA-N nateglinide Chemical compound C1C[C@@H](C(C)C)CC[C@@H]1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-BRWVUGGUSA-N 0.000 description 1
229960000698 nateglinide Drugs 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
208000015238 neurotic disease Diseases 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229960001783 nicardipine Drugs 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
HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
229960001597 nifedipine Drugs 0.000 description 1
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 description 1
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
229960001199 olmesartan medoxomil Drugs 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
229960001243 orlistat Drugs 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
VCCZBYPHZRWKFY-XIKOKIGWSA-N oxazolam Chemical compound C1([C@]23C4=CC(Cl)=CC=C4NC(=O)CN2C[C@H](O3)C)=CC=CC=C1 VCCZBYPHZRWKFY-XIKOKIGWSA-N 0.000 description 1
229950006124 oxazolam Drugs 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
XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 description 1
229960001723 oxytocin Drugs 0.000 description 1
229960002296 paroxetine Drugs 0.000 description 1
239000008188 pellet Substances 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
FDJABJJEKWDNQO-UHFFFAOYSA-N pentane;propan-2-one Chemical compound CC(C)=O.CCCCC FDJABJJEKWDNQO-UHFFFAOYSA-N 0.000 description 1
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
DIXJUXSGSZCZCO-UHFFFAOYSA-N phenazine;10h-phenothiazine Chemical compound C1=CC=CC2=NC3=CC=CC=C3N=C21.C1=CC=C2NC3=CC=CC=C3SC2=C1 DIXJUXSGSZCZCO-UHFFFAOYSA-N 0.000 description 1
229960003243 phenformin Drugs 0.000 description 1
ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 1
229950000688 phenothiazine Drugs 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
229940067157 phenylhydrazine Drugs 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
125000005633 phthalidyl group Chemical group 0.000 description 1
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
239000006187 pill Substances 0.000 description 1
229960003890 pimagedine Drugs 0.000 description 1
229960005095 pioglitazone Drugs 0.000 description 1
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
229960002797 pitavastatin Drugs 0.000 description 1
VGYFMXBACGZSIL-MCBHFWOFSA-N pitavastatin Chemical compound OC(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 VGYFMXBACGZSIL-MCBHFWOFSA-N 0.000 description 1
230000001817 pituitary effect Effects 0.000 description 1
229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 1
239000013612 plasmid Substances 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
UZJBOHHDWXQTEF-UHFFFAOYSA-N pocl3 pyridine Chemical compound ClP(Cl)(Cl)=O.C1=CC=NC=C1 UZJBOHHDWXQTEF-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
229910000343 potassium bisulfate Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
TZIRZGBAFTZREM-MKAGXXMWSA-N pramlintide Chemical compound C([C@@H](C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H]1NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CCCCN)CSSC1)[C@@H](C)O)C(C)C)C1=CC=CC=C1 TZIRZGBAFTZREM-MKAGXXMWSA-N 0.000 description 1
229960003611 pramlintide Drugs 0.000 description 1
108010029667 pramlintide Proteins 0.000 description 1
229960002965 pravastatin Drugs 0.000 description 1
TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
238000004262 preparative liquid chromatography Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
239000013615 primer Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
AMLFJZRZIOZGPW-UHFFFAOYSA-N prop-1-en-1-amine Chemical compound CC=CN AMLFJZRZIOZGPW-UHFFFAOYSA-N 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 1
229950008679 protamine sulfate Drugs 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
YOXCYXPIIFUVDQ-UHFFFAOYSA-N pyridine;thionyl dichloride Chemical compound ClS(Cl)=O.C1=CC=NC=C1 YOXCYXPIIFUVDQ-UHFFFAOYSA-N 0.000 description 1
SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000006215 rectal suppository Substances 0.000 description 1
235000018770 reduced food intake Nutrition 0.000 description 1
238000001028 reflection method Methods 0.000 description 1
229960002354 repaglinide Drugs 0.000 description 1
238000011160 research Methods 0.000 description 1
238000012827 research and development Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
229960004586 rosiglitazone Drugs 0.000 description 1
LALFOYNTGMUKGG-BGRFNVSISA-L rosuvastatin calcium Chemical compound [Ca+2].CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O.CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O LALFOYNTGMUKGG-BGRFNVSISA-L 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 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
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
231100000872 sexual dysfunction Toxicity 0.000 description 1
UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 1
229960004425 sibutramine Drugs 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229960004058 simfibrate Drugs 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
229960002855 simvastatin Drugs 0.000 description 1
RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
229940032147 starch Drugs 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
229960004084 temocapril Drugs 0.000 description 1
FIQOFIRCTOWDOW-BJLQDIEVSA-N temocapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C[C@H](SC1)C=1SC=CC=1)=O)CC1=CC=CC=C1 FIQOFIRCTOWDOW-BJLQDIEVSA-N 0.000 description 1
BFSMEUZIFDZIFM-UHFFFAOYSA-N tert-butyl 8-hydroxy-1,3,4,5-tetrahydro-2-benzazepine-2-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC2=CC=C(O)C=C21 BFSMEUZIFDZIFM-UHFFFAOYSA-N 0.000 description 1
MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 1
DNXJECSBZXVFLB-UHFFFAOYSA-N tert-butyl n-[2-[4-(4-fluorophenyl)piperazin-1-yl]-2-oxoethyl]carbamate Chemical compound C1CN(C(=O)CNC(=O)OC(C)(C)C)CCN1C1=CC=C(F)C=C1 DNXJECSBZXVFLB-UHFFFAOYSA-N 0.000 description 1
ZXLDQJLIBNPEFJ-UHFFFAOYSA-N tetrahydro-beta-carboline Natural products C1CNC(C)C2=C1C1=CC=C(OC)C=C1N2 ZXLDQJLIBNPEFJ-UHFFFAOYSA-N 0.000 description 1
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
229940113082 thymine Drugs 0.000 description 1
229960005344 tiapride Drugs 0.000 description 1
229960002277 tolazamide Drugs 0.000 description 1
OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 description 1
229960005371 tolbutamide Drugs 0.000 description 1
LUBHDINQXIHVLS-UHFFFAOYSA-N tolrestat Chemical compound OC(=O)CN(C)C(=S)C1=CC=CC2=C(C(F)(F)F)C(OC)=CC=C21 LUBHDINQXIHVLS-UHFFFAOYSA-N 0.000 description 1
229960003069 tolrestat Drugs 0.000 description 1
239000012929 tonicity agent Substances 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
229960002051 trandolapril Drugs 0.000 description 1
238000010361 transduction Methods 0.000 description 1
230000026683 transduction Effects 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
229960001641 troglitazone Drugs 0.000 description 1
GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
239000006216 vaginal suppository Substances 0.000 description 1
229960004699 valsartan Drugs 0.000 description 1
SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 description 1
229960003726 vasopressin Drugs 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
229960001729 voglibose Drugs 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
SXONDGSPUVNZLO-UHFFFAOYSA-N zenarestat Chemical compound O=C1N(CC(=O)O)C2=CC(Cl)=CC=C2C(=O)N1CC1=CC=C(Br)C=C1F SXONDGSPUVNZLO-UHFFFAOYSA-N 0.000 description 1
229950006343 zenarestat Drugs 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
229950005346 zopolrestat Drugs 0.000 description 1