TWI460176B - 吲哚化合物 - Google Patents

Info

Publication number

TWI460176B

TWI460176B TW096138971A TW96138971A TWI460176B TW I460176 B TWI460176 B TW I460176B TW 096138971 A TW096138971 A TW 096138971A TW 96138971 A TW96138971 A TW 96138971A TW I460176 B TWI460176 B TW I460176B

Authority

TW

Taiwan

Prior art keywords

group

compound

optionally substituted

alkyl

methyl

Prior art date

2006-10-19

Links

• Espacenet
• Global Dossier
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• -1 Indole compound Chemical class 0.000 title claims description 364
• SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title 1
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title 1
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 418
• 125000001424 substituent group Chemical group 0.000 claims description 186
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 125
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 119
• 125000005843 halogen group Chemical group 0.000 claims description 111
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 96
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 94
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 78
• 125000000217 alkyl group Chemical group 0.000 claims description 70
• 150000003839 salts Chemical class 0.000 claims description 63
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 50
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 46
• 150000001412 amines Chemical class 0.000 claims description 44
• 206010012601 diabetes mellitus Diseases 0.000 claims description 30
• 125000004076 pyridyl group Chemical group 0.000 claims description 26
• 239000003814 drug Substances 0.000 claims description 25
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 24
• 125000002757 morpholinyl group Chemical group 0.000 claims description 21
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 16
• 208000008589 Obesity Diseases 0.000 claims description 15
• 235000020824 obesity Nutrition 0.000 claims description 15
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 12
• 125000001544 thienyl group Chemical group 0.000 claims description 12
• 238000004519 manufacturing process Methods 0.000 claims description 7
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
• 229940124828 glucokinase activator Drugs 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
• KTFDYVNEGTXQCV-UHFFFAOYSA-N 2-Thiophenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CS1 KTFDYVNEGTXQCV-UHFFFAOYSA-N 0.000 claims description 3
• WUSORUOKYAMODH-UHFFFAOYSA-N 2-[2-[7-[methyl(thiophen-2-ylsulfonyl)amino]-5-(trifluoromethoxy)-1h-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl]acetamide Chemical compound C=1C=CSC=1S(=O)(=O)N(C)C(C=1N2)=CC(OC(F)(F)F)=CC=1C=C2C1=NCC(CC(N)=O)S1 WUSORUOKYAMODH-UHFFFAOYSA-N 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• VMLXKJNHVAVBTR-UHFFFAOYSA-N n-(difluoromethyl)-n-[2-[5-(morpholin-4-ylmethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1h-indol-7-yl]thiophene-2-sulfonamide Chemical compound C=1C=CSC=1S(=O)(=O)N(C(F)F)C(C=1N2)=CC=CC=1C=C2C(S1)=NCC1CN1CCOCC1 VMLXKJNHVAVBTR-UHFFFAOYSA-N 0.000 claims description 3
• 238000006243 chemical reaction Methods 0.000 description 161
• 125000006615 aromatic heterocyclic group Chemical group 0.000 description 137
• 239000002904 solvent Substances 0.000 description 99
• 239000002585 base Substances 0.000 description 90
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 77
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 72
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 70
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 69
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 67
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
• 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 58
• 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 58
• 239000008103 glucose Substances 0.000 description 58
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
• 235000002639 sodium chloride Nutrition 0.000 description 52
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 50
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 50
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 49
• 239000000203 mixture Substances 0.000 description 49
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 47
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 47
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 47
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 45
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 44
• 125000001183 hydrocarbyl group Chemical group 0.000 description 44
• 125000000623 heterocyclic group Chemical group 0.000 description 42
• 238000000034 method Methods 0.000 description 42
• 125000003118 aryl group Chemical group 0.000 description 41
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 39
• 125000003545 alkoxy group Chemical group 0.000 description 39
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 36
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 36
• 229910052731 fluorine Inorganic materials 0.000 description 35
• 125000001153 fluoro group Chemical group F* 0.000 description 35
• 239000000243 solution Substances 0.000 description 35
• 108010021582 Glucokinase Proteins 0.000 description 33
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 32
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 31
• 235000019441 ethanol Nutrition 0.000 description 31
• 230000035484 reaction time Effects 0.000 description 31
• USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 30
• 125000003277 amino group Chemical group 0.000 description 29
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 28
• 150000001335 aliphatic alkanes Chemical class 0.000 description 28
• 239000003638 chemical reducing agent Substances 0.000 description 28
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 28
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 28
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 27
• 125000002950 monocyclic group Chemical group 0.000 description 27
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 25
• 239000003795 chemical substances by application Substances 0.000 description 25
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 25
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 25
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 24
• 210000004369 blood Anatomy 0.000 description 24
• 239000008280 blood Substances 0.000 description 24
• 125000004093 cyano group Chemical group *C#N 0.000 description 24
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 23
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 23
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 22
• 229910052757 nitrogen Inorganic materials 0.000 description 22
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
• 238000002360 preparation method Methods 0.000 description 22
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 21
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 21
• 150000002170 ethers Chemical class 0.000 description 21
• 125000001425 triazolyl group Chemical group 0.000 description 21
• 125000005915 C6-C14 aryl group Chemical group 0.000 description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 20
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 20
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 19
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 19
• 125000003710 aryl alkyl group Chemical group 0.000 description 19
• 235000019439 ethyl acetate Nutrition 0.000 description 19
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 19
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 19
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 18
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 18
• 239000013078 crystal Substances 0.000 description 18
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 18
• 125000002541 furyl group Chemical group 0.000 description 18
• 239000001257 hydrogen Substances 0.000 description 18
• 229910052739 hydrogen Inorganic materials 0.000 description 18
• 229930195734 saturated hydrocarbon Natural products 0.000 description 18
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
• UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 17
• 229910052801 chlorine Inorganic materials 0.000 description 17
• 238000006722 reduction reaction Methods 0.000 description 17
• 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 16
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 16
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
• 235000011054 acetic acid Nutrition 0.000 description 16
• 239000003377 acid catalyst Substances 0.000 description 16
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 16
• 125000001309 chloro group Chemical group Cl* 0.000 description 16
• 235000019253 formic acid Nutrition 0.000 description 16
• 229940124597 therapeutic agent Drugs 0.000 description 16
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
• 125000002883 imidazolyl group Chemical group 0.000 description 15
• VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 15
• 150000007524 organic acids Chemical class 0.000 description 15
• 125000005530 alkylenedioxy group Chemical group 0.000 description 14
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 14
• 125000004433 nitrogen atom Chemical group N* 0.000 description 14
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 14
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 13
• 239000003112 inhibitor Substances 0.000 description 13
• 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 13
• 229910052751 metal Inorganic materials 0.000 description 13
• 239000002184 metal Substances 0.000 description 13
• 125000003386 piperidinyl group Chemical group 0.000 description 13
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
• 239000011541 reaction mixture Substances 0.000 description 13
• BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 13
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 12
• 150000001298 alcohols Chemical class 0.000 description 12
• 230000000694 effects Effects 0.000 description 12
• 238000001990 intravenous administration Methods 0.000 description 12
• 235000005985 organic acids Nutrition 0.000 description 12
• 239000003054 catalyst Substances 0.000 description 11
• 229930195733 hydrocarbon Natural products 0.000 description 11
• 150000002430 hydrocarbons Chemical group 0.000 description 11
• 229910000027 potassium carbonate Inorganic materials 0.000 description 11
• 235000011181 potassium carbonates Nutrition 0.000 description 11
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
• 239000002253 acid Substances 0.000 description 10
• 229910052783 alkali metal Inorganic materials 0.000 description 10
• 229910000085 borane Inorganic materials 0.000 description 10
• DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 10
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
• 150000008282 halocarbons Chemical class 0.000 description 10
• 238000002844 melting Methods 0.000 description 10
• 230000008018 melting Effects 0.000 description 10
• 229910052987 metal hydride Inorganic materials 0.000 description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 10
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
• 125000000335 thiazolyl group Chemical group 0.000 description 10
• 125000004568 thiomorpholinyl group Chemical group 0.000 description 10
• 206010006895 Cachexia Diseases 0.000 description 9
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
• 229940000425 combination drug Drugs 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
• 150000002148 esters Chemical class 0.000 description 9
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 9
• 230000003914 insulin secretion Effects 0.000 description 9
• 150000002825 nitriles Chemical class 0.000 description 9
• 229940002612 prodrug Drugs 0.000 description 9
• 239000000651 prodrug Substances 0.000 description 9
• FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 9
• 125000003226 pyrazolyl group Chemical group 0.000 description 9
• 125000003831 tetrazolyl group Chemical group 0.000 description 9
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
• XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 8
• 230000005856 abnormality Effects 0.000 description 8
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 8
• 125000004429 atom Chemical group 0.000 description 8
• 125000002393 azetidinyl group Chemical group 0.000 description 8
• 150000007530 organic bases Chemical class 0.000 description 8
• 125000006239 protecting group Chemical group 0.000 description 8
• 125000002755 pyrazolinyl group Chemical group 0.000 description 8
• 229910000029 sodium carbonate Inorganic materials 0.000 description 8
• 235000017550 sodium carbonate Nutrition 0.000 description 8
• 239000007858 starting material Substances 0.000 description 8
• UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 8
• 229940086542 triethylamine Drugs 0.000 description 8
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 7
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 7
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
• 210000002237 B-cell of pancreatic islet Anatomy 0.000 description 7
• 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 description 7
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