PH26766A - Thiazole derivatives and pharmaceutical composition containing said compound - Google Patents
Thiazole derivatives and pharmaceutical composition containing said compound Download PDFInfo
- Publication number
- PH26766A PH26766A PH40861A PH40861A PH26766A PH 26766 A PH26766 A PH 26766A PH 40861 A PH40861 A PH 40861A PH 40861 A PH40861 A PH 40861A PH 26766 A PH26766 A PH 26766A
- Authority
- PH
- Philippines
- Prior art keywords
- mixture
- amino
- compound
- thiazole
- give
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 111
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
- 150000007979 thiazole derivatives Chemical class 0.000 title description 9
- -1 nitro, amino Chemical group 0.000 claims abstract description 94
- 150000003839 salts Chemical class 0.000 claims abstract description 55
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 36
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 18
- 125000005843 halogen group Chemical group 0.000 claims abstract description 14
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 3
- 239000004480 active ingredient Substances 0.000 claims abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000001589 carboacyl group Chemical group 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 45
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 9
- 125000002252 acyl group Chemical group 0.000 abstract description 6
- 125000003118 aryl group Chemical group 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 5
- 125000004442 acylamino group Chemical group 0.000 abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
- 239000003937 drug carrier Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 201
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 120
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 110
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 91
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 90
- 238000003756 stirring Methods 0.000 description 85
- 239000007787 solid Substances 0.000 description 67
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 64
- 239000011541 reaction mixture Substances 0.000 description 64
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- 238000006243 chemical reaction Methods 0.000 description 59
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 56
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 54
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 53
- 238000001914 filtration Methods 0.000 description 51
- 239000000243 solution Substances 0.000 description 51
- 239000002244 precipitate Substances 0.000 description 46
- 239000002904 solvent Substances 0.000 description 46
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 43
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 42
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
- 239000000741 silica gel Substances 0.000 description 33
- 229910002027 silica gel Inorganic materials 0.000 description 33
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 28
- 235000017557 sodium bicarbonate Nutrition 0.000 description 28
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 27
- 235000019341 magnesium sulphate Nutrition 0.000 description 27
- 238000001816 cooling Methods 0.000 description 26
- 239000002253 acid Substances 0.000 description 24
- 238000004440 column chromatography Methods 0.000 description 24
- 235000011054 acetic acid Nutrition 0.000 description 21
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 21
- 235000011181 potassium carbonates Nutrition 0.000 description 21
- 229910000027 potassium carbonate Inorganic materials 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 241000699670 Mus sp. Species 0.000 description 14
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- 239000005457 ice water Substances 0.000 description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 230000002411 adverse Effects 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 238000010792 warming Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 239000002246 antineoplastic agent Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 238000011765 DBA/2 mouse Methods 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 230000002140 halogenating effect Effects 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 150000002443 hydroxylamines Chemical class 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- LHWHLINDRWCHSN-UHFFFAOYSA-N n-(5-bromo-1,3-thiazol-2-yl)acetamide Chemical compound CC(=O)NC1=NC=C(Br)S1 LHWHLINDRWCHSN-UHFFFAOYSA-N 0.000 description 4
- YLRXYIGXXMJPOP-UHFFFAOYSA-N n-(5-chloro-1,3-thiazol-2-yl)acetamide Chemical compound CC(=O)NC1=NC=C(Cl)S1 YLRXYIGXXMJPOP-UHFFFAOYSA-N 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- AXBVSRMHOPMXBA-UHFFFAOYSA-N 4-nitrothiophenol Chemical compound [O-][N+](=O)C1=CC=C(S)C=C1 AXBVSRMHOPMXBA-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 230000001518 anti-nephritic effect Effects 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 229960004857 mitomycin Drugs 0.000 description 3
- 201000008383 nephritis Diseases 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 206010043554 thrombocytopenia Diseases 0.000 description 3
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- FHTDDANQIMVWKZ-UHFFFAOYSA-N 1h-pyridine-4-thione Chemical compound SC1=CC=NC=C1 FHTDDANQIMVWKZ-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-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
- XBDGDAQTSPPQAL-UHFFFAOYSA-N 5-(1h-imidazol-2-ylsulfanyl)-1,3-thiazol-2-amine Chemical compound S1C(N)=NC=C1SC1=NC=CN1 XBDGDAQTSPPQAL-UHFFFAOYSA-N 0.000 description 2
- MRIJQSOIHVDNLA-UHFFFAOYSA-N 5-(4-aminophenyl)sulfanyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC=C1SC1=CC=C(N)C=C1 MRIJQSOIHVDNLA-UHFFFAOYSA-N 0.000 description 2
- SKNZYVZWFOSLLC-UHFFFAOYSA-N 5-pyridin-4-ylsulfanyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC=C1SC1=CC=NC=C1 SKNZYVZWFOSLLC-UHFFFAOYSA-N 0.000 description 2
- DCPSTSVLRXOYGS-UHFFFAOYSA-N 6-amino-1h-pyrimidine-2-thione Chemical compound NC1=CC=NC(S)=N1 DCPSTSVLRXOYGS-UHFFFAOYSA-N 0.000 description 2
- 102000009027 Albumins Human genes 0.000 description 2
- 108010088751 Albumins Proteins 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 241000206607 Porphyra umbilicalis Species 0.000 description 2
- 102000007562 Serum Albumin Human genes 0.000 description 2
- 108010071390 Serum Albumin Proteins 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000003356 anti-rheumatic effect Effects 0.000 description 2
- 230000002917 arthritic effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
- 208000024908 graft versus host disease Diseases 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 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
- 150000007522 mineralic acids Chemical class 0.000 description 2
- JLCDWEXOPUCWQA-UHFFFAOYSA-N n-[4-[(2-formamido-1,3-thiazol-4-yl)methylsulfanyl]phenyl]formamide Chemical compound S1C(NC=O)=NC(CSC=2C=CC(NC=O)=CC=2)=C1 JLCDWEXOPUCWQA-UHFFFAOYSA-N 0.000 description 2
- KZYGZLIHDNUQDU-UHFFFAOYSA-N n-[4-[(4-nitrophenyl)sulfanylmethyl]-1,3-thiazol-2-yl]formamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1SCC1=CSC(NC=O)=N1 KZYGZLIHDNUQDU-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- SOGUKVNWIVUCMA-UHFFFAOYSA-N (2-amino-1,3-thiazol-4-yl)-(4-nitrophenyl)methanone Chemical compound S1C(N)=NC(C(=O)C=2C=CC(=CC=2)[N+]([O-])=O)=C1 SOGUKVNWIVUCMA-UHFFFAOYSA-N 0.000 description 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 1
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-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
- JSQPGNJFQUOEPA-UHFFFAOYSA-N 2-chloroethaneperoxoic acid Chemical compound OOC(=O)CCl JSQPGNJFQUOEPA-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- GUIUCBALKSVLSZ-UHFFFAOYSA-N 3-chloro-1-(4-nitrophenyl)propane-1,2-dione Chemical compound [O-][N+](=O)C1=CC=C(C(=O)C(=O)CCl)C=C1 GUIUCBALKSVLSZ-UHFFFAOYSA-N 0.000 description 1
- MARYDOMJDFATPK-UHFFFAOYSA-N 3-hydroxy-1h-pyridine-2-thione Chemical compound OC1=CC=CN=C1S MARYDOMJDFATPK-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
- JFEIBBLIEMLTJL-UHFFFAOYSA-N 4-[(2-amino-1,3-thiazol-5-yl)sulfanyl]phenol Chemical compound S1C(N)=NC=C1SC1=CC=C(O)C=C1 JFEIBBLIEMLTJL-UHFFFAOYSA-N 0.000 description 1
- INNOTKNFFHFMQL-UHFFFAOYSA-N 4-[(4-aminophenyl)sulfanylmethyl]-5-chloro-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(CSC=2C=CC(N)=CC=2)=C1Cl INNOTKNFFHFMQL-UHFFFAOYSA-N 0.000 description 1
- HYRFFAYNEPHSMD-UHFFFAOYSA-N 4-[(4-aminophenyl)sulfinylmethyl]-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(CS(=O)C=2C=CC(N)=CC=2)=C1 HYRFFAYNEPHSMD-UHFFFAOYSA-N 0.000 description 1
- LKDGPNLAUXLAAK-UHFFFAOYSA-N 4-[(4-aminophenyl)sulfonylmethyl]-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(CS(=O)(=O)C=2C=CC(N)=CC=2)=C1 LKDGPNLAUXLAAK-UHFFFAOYSA-N 0.000 description 1
- AGOWMJFPYPUNRF-UHFFFAOYSA-N 4-[(4-nitrophenyl)sulfanylmethyl]-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(CSC=2C=CC(=CC=2)[N+]([O-])=O)=C1 AGOWMJFPYPUNRF-UHFFFAOYSA-N 0.000 description 1
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 1
- NIFAOMSJMGEFTQ-UHFFFAOYSA-N 4-methoxybenzenethiol Chemical compound COC1=CC=C(S)C=C1 NIFAOMSJMGEFTQ-UHFFFAOYSA-N 0.000 description 1
- QRICMJIFKNUFGT-UHFFFAOYSA-N 4-methyl-5-[(4-nitrophenyl)methyl]-1,3-thiazol-2-amine Chemical compound N1=C(N)SC(CC=2C=CC(=CC=2)[N+]([O-])=O)=C1C QRICMJIFKNUFGT-UHFFFAOYSA-N 0.000 description 1
- SYJSLLQWSIHKKR-UHFFFAOYSA-N 4-methyl-5-pyridin-2-ylsulfanyl-1,3-thiazol-2-amine Chemical compound N1=C(N)SC(SC=2N=CC=CC=2)=C1C SYJSLLQWSIHKKR-UHFFFAOYSA-N 0.000 description 1
- BXAVKNRWVKUTLY-UHFFFAOYSA-N 4-sulfanylphenol Chemical compound OC1=CC=C(S)C=C1 BXAVKNRWVKUTLY-UHFFFAOYSA-N 0.000 description 1
- WVGHYAJLXSMXPF-UHFFFAOYSA-N 5-(4-aminophenyl)sulfinyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC=C1S(=O)C1=CC=C(N)C=C1 WVGHYAJLXSMXPF-UHFFFAOYSA-N 0.000 description 1
- KNTSHQYSZLXVSM-UHFFFAOYSA-N 5-(4-aminopyrimidin-2-yl)sulfanyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC=C1SC1=NC=CC(N)=N1 KNTSHQYSZLXVSM-UHFFFAOYSA-N 0.000 description 1
- HUSCQWZPKFWILI-UHFFFAOYSA-N 5-(4-methoxyphenyl)sulfanyl-1,3-thiazol-2-amine Chemical compound C1=CC(OC)=CC=C1SC1=CN=C(N)S1 HUSCQWZPKFWILI-UHFFFAOYSA-N 0.000 description 1
- SDUBXOMNMUMRQT-UHFFFAOYSA-N 5-(4-methylpyrimidin-2-yl)sulfanyl-1,3-thiazol-2-amine Chemical compound CC1=CC=NC(SC=2SC(N)=NC=2)=N1 SDUBXOMNMUMRQT-UHFFFAOYSA-N 0.000 description 1
- ROYXOYGGUFKXGS-UHFFFAOYSA-N 5-(4-nitrophenyl)sulfanyl-1,3-thiazol-2-amine Chemical class S1C(N)=NC=C1SC1=CC=C([N+]([O-])=O)C=C1 ROYXOYGGUFKXGS-UHFFFAOYSA-N 0.000 description 1
- SGDKTJPVCKQTHK-UHFFFAOYSA-N 5-bromo-2-fluoro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC(Br)=CN=C1F SGDKTJPVCKQTHK-UHFFFAOYSA-N 0.000 description 1
- QDFZHFCNGXKPJU-UHFFFAOYSA-N 5-pyridin-2-ylsulfinyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC=C1S(=O)C1=CC=CC=N1 QDFZHFCNGXKPJU-UHFFFAOYSA-N 0.000 description 1
- GLMVXPXJSIRYDN-UHFFFAOYSA-N 5-pyridin-3-ylsulfinyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC=C1S(=O)C1=CC=CN=C1 GLMVXPXJSIRYDN-UHFFFAOYSA-N 0.000 description 1
- GOODPCCXPDYFSP-UHFFFAOYSA-N 5-pyridin-3-ylsulfonyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC=C1S(=O)(=O)C1=CC=CN=C1 GOODPCCXPDYFSP-UHFFFAOYSA-N 0.000 description 1
- FJPGOARRTGGOAK-UHFFFAOYSA-N 5-pyridin-4-ylsulfinyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC=C1S(=O)C1=CC=NC=C1 FJPGOARRTGGOAK-UHFFFAOYSA-N 0.000 description 1
- ZFGVHIOWIYRDOB-UHFFFAOYSA-N 5-pyrimidin-2-ylsulfanyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC=C1SC1=NC=CC=N1 ZFGVHIOWIYRDOB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-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
- 208000008822 Ankylosis Diseases 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 101100203601 Caenorhabditis elegans sor-3 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229910021555 Chromium Chloride Inorganic materials 0.000 description 1
- MQWAIHYBJZHYTH-UHFFFAOYSA-N Cl.Cc1ncsc1N Chemical compound Cl.Cc1ncsc1N MQWAIHYBJZHYTH-UHFFFAOYSA-N 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 102000000503 Collagen Type II Human genes 0.000 description 1
- 108010041390 Collagen Type II Proteins 0.000 description 1
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 208000009386 Experimental Arthritis Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 description 1
- 206010023198 Joint ankylosis 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
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 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
- 239000012448 Lithium borohydride Substances 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 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
- IPCRBOOJBPETMF-UHFFFAOYSA-N N-acetylthiourea Chemical compound CC(=O)NC(N)=S IPCRBOOJBPETMF-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
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 description 1
- 206010043561 Thrombocytopenic purpura Diseases 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000000702 anti-platelet effect Effects 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical class C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- SIOVKLKJSOKLIF-UHFFFAOYSA-N bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)OC(C)=N[Si](C)(C)C SIOVKLKJSOKLIF-UHFFFAOYSA-N 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
- WYYQVWLEPYFFLP-UHFFFAOYSA-K chromium(3+);triacetate Chemical compound [Cr+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WYYQVWLEPYFFLP-UHFFFAOYSA-K 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 1
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000020176 deacylation Effects 0.000 description 1
- 238000005947 deacylation reaction Methods 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000000499 gel Substances 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
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 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 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 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
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Inorganic materials Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 230000000951 immunodiffusion Effects 0.000 description 1
- 230000001965 increasing effect Effects 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 150000004966 inorganic peroxy acids Chemical class 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229940031703 low substituted hydroxypropyl cellulose Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910012375 magnesium hydride Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- VDCLSGXZVUDARN-UHFFFAOYSA-N molecular bromine;pyridine;hydrobromide Chemical compound Br.BrBr.C1=CC=NC=C1 VDCLSGXZVUDARN-UHFFFAOYSA-N 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- NSBNSZAXNUGWDJ-UHFFFAOYSA-O monopyridin-1-ium tribromide Chemical compound Br[Br-]Br.C1=CC=[NH+]C=C1 NSBNSZAXNUGWDJ-UHFFFAOYSA-O 0.000 description 1
- BSIRERMABQPXIJ-UHFFFAOYSA-N n-(5-pyridin-4-ylsulfanyl-1,3-thiazol-2-yl)acetamide Chemical compound S1C(NC(=O)C)=NC=C1SC1=CC=NC=C1 BSIRERMABQPXIJ-UHFFFAOYSA-N 0.000 description 1
- YLVAJMXHCTYFQK-UHFFFAOYSA-N n-(5-pyrimidin-2-ylsulfanyl-1,3-thiazol-2-yl)acetamide Chemical compound S1C(NC(=O)C)=NC=C1SC1=NC=CC=N1 YLVAJMXHCTYFQK-UHFFFAOYSA-N 0.000 description 1
- IAWQHJBMHBLBEN-UHFFFAOYSA-N n-[4-(chloromethyl)-1,3-thiazol-2-yl]formamide Chemical compound ClCC1=CSC(NC=O)=N1 IAWQHJBMHBLBEN-UHFFFAOYSA-N 0.000 description 1
- XRXOHGHYAPSJAV-UHFFFAOYSA-N n-[4-(hydroxymethyl)-1,3-thiazol-2-yl]acetamide Chemical compound CC(=O)NC1=NC(CO)=CS1 XRXOHGHYAPSJAV-UHFFFAOYSA-N 0.000 description 1
- ACRKCWFJDZKGIJ-UHFFFAOYSA-N n-[4-(pyridin-4-ylsulfanylmethyl)-1,3-thiazol-2-yl]formamide Chemical compound S1C(NC=O)=NC(CSC=2C=CN=CC=2)=C1 ACRKCWFJDZKGIJ-UHFFFAOYSA-N 0.000 description 1
- HGZBYRWRDGLWLN-UHFFFAOYSA-N n-[4-[(2-amino-1,3-thiazol-5-yl)sulfanyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1SC1=CN=C(N)S1 HGZBYRWRDGLWLN-UHFFFAOYSA-N 0.000 description 1
- LSIHHSBYXRFAAA-UHFFFAOYSA-N n-[4-[(4-aminophenyl)sulfanylmethyl]-1,3-thiazol-2-yl]formamide Chemical compound C1=CC(N)=CC=C1SCC1=CSC(NC=O)=N1 LSIHHSBYXRFAAA-UHFFFAOYSA-N 0.000 description 1
- ZBDNQWQMSKJGSW-UHFFFAOYSA-N n-[4-[(4-nitrophenyl)sulfanylmethyl]-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(CSC=2C=CC(=CC=2)[N+]([O-])=O)=C1 ZBDNQWQMSKJGSW-UHFFFAOYSA-N 0.000 description 1
- FQELCZDDZJLVCU-UHFFFAOYSA-N n-[5-(1-methylimidazol-2-yl)sulfanyl-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC=C1SC1=NC=CN1C FQELCZDDZJLVCU-UHFFFAOYSA-N 0.000 description 1
- JMWYHCSCABWKOY-UHFFFAOYSA-N n-[5-(1-methyltetrazol-5-yl)sulfanyl-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC=C1SC1=NN=NN1C JMWYHCSCABWKOY-UHFFFAOYSA-N 0.000 description 1
- VVOQVSGYCSEURF-UHFFFAOYSA-N n-[5-(4-methoxyphenyl)sulfanyl-1,3-thiazol-2-yl]acetamide Chemical compound C1=CC(OC)=CC=C1SC1=CN=C(NC(C)=O)S1 VVOQVSGYCSEURF-UHFFFAOYSA-N 0.000 description 1
- HGWAIWDCZJHBBG-UHFFFAOYSA-N n-[5-(4-methylpyrimidin-2-yl)sulfanyl-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC=C1SC1=NC=CC(C)=N1 HGWAIWDCZJHBBG-UHFFFAOYSA-N 0.000 description 1
- YKTLZNQOOIRKMH-UHFFFAOYSA-N n-[5-(4-nitrophenyl)sulfanyl-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC=C1SC1=CC=C([N+]([O-])=O)C=C1 YKTLZNQOOIRKMH-UHFFFAOYSA-N 0.000 description 1
- XVHDXLCRZFRXSO-UHFFFAOYSA-N n-[5-(4-nitrophenyl)sulfanyl-1,3-thiazol-2-yl]propanamide Chemical compound S1C(NC(=O)CC)=NC=C1SC1=CC=C([N+]([O-])=O)C=C1 XVHDXLCRZFRXSO-UHFFFAOYSA-N 0.000 description 1
- VTQFQIIUWABUIC-UHFFFAOYSA-N n-[5-[(6-oxo-1h-pyrimidin-2-yl)sulfanyl]-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC=C1SC1=NC=CC(O)=N1 VTQFQIIUWABUIC-UHFFFAOYSA-N 0.000 description 1
- SDMRNRDAPWKAQJ-UHFFFAOYSA-N n-[5-chloro-4-(pyridin-4-ylsulfanylmethyl)-1,3-thiazol-2-yl]formamide Chemical compound S1C(NC=O)=NC(CSC=2C=CN=CC=2)=C1Cl SDMRNRDAPWKAQJ-UHFFFAOYSA-N 0.000 description 1
- MIHKDEWBESXPGS-UHFFFAOYSA-N n-carbamothioylformamide Chemical compound NC(=S)NC=O MIHKDEWBESXPGS-UHFFFAOYSA-N 0.000 description 1
- VVWCJSVUWOIXAD-UHFFFAOYSA-N n-carbamothioylpropanamide Chemical compound CCC(=O)NC(N)=S VVWCJSVUWOIXAD-UHFFFAOYSA-N 0.000 description 1
- LWFWUJCJKPUZLV-UHFFFAOYSA-N n-trimethylsilylacetamide Chemical compound CC(=O)N[Si](C)(C)C LWFWUJCJKPUZLV-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluenecarboxylic acid Natural products CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000004968 peroxymonosulfuric acids Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 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
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 201000001474 proteinuria Diseases 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- FFWJHVGUAKWTKW-UHFFFAOYSA-N pyridine-3-thiol Chemical compound SC1=CC=CN=C1 FFWJHVGUAKWTKW-UHFFFAOYSA-N 0.000 description 1
- BSGNUSYRRYIFLP-UHFFFAOYSA-N pyridine-3-thiol;hydrochloride Chemical compound Cl.SC1=CC=CN=C1 BSGNUSYRRYIFLP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 210000004989 spleen cell Anatomy 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
- WQEVDHBJGNOKKO-UHFFFAOYSA-K vanadic acid Chemical compound O[V](O)(O)=O WQEVDHBJGNOKKO-UHFFFAOYSA-K 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/54—Nitrogen and either oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB898918045A GB8918045D0 (en) | 1989-08-07 | 1989-08-07 | Thiazole derivatives,processes for production thereof and pharmaceutical compositions comprising the same |
| GB909003930A GB9003930D0 (en) | 1990-02-21 | 1990-02-21 | Thiazole derivatives,processes for production thereof and pharmaceutical compositions comprising the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26766A true PH26766A (en) | 1992-09-28 |
Family
ID=26295715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH40861A PH26766A (en) | 1989-08-07 | 1990-07-19 | Thiazole derivatives and pharmaceutical composition containing said compound |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP0412404B1 (fi) |
| JP (1) | JPH0368567A (fi) |
| KR (1) | KR910004582A (fi) |
| CN (1) | CN1027370C (fi) |
| AT (1) | ATE133667T1 (fi) |
| AU (1) | AU635758B2 (fi) |
| CA (1) | CA2022731A1 (fi) |
| DE (1) | DE69025104T2 (fi) |
| DK (1) | DK0412404T3 (fi) |
| ES (1) | ES2082805T3 (fi) |
| FI (1) | FI96857C (fi) |
| GR (1) | GR3019009T3 (fi) |
| HK (1) | HK151596A (fi) |
| HU (2) | HUT57752A (fi) |
| IE (1) | IE902679A1 (fi) |
| IL (1) | IL95281A (fi) |
| NO (1) | NO179638C (fi) |
| PH (1) | PH26766A (fi) |
| PT (1) | PT94925B (fi) |
| RU (2) | RU2010026C1 (fi) |
| TW (1) | TW205041B (fi) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU644281B2 (en) * | 1991-04-24 | 1993-12-02 | Sumitomo Pharmaceuticals Company, Limited | Novel thiazole derivatives |
| FR2677021B1 (fr) * | 1991-05-31 | 1993-10-01 | Upsa Laboratoires | Nouveaux derives de thiazole antagonistes des recepteurs a l'angiotensine ii; leurs procedes de preparation, compositions pharmaceutiques les contenant. |
| DE4119756A1 (de) * | 1991-06-15 | 1992-12-17 | Basf Ag | Aminoalkylsubstituierte 5-mercaptothiazole, ihre herstellung und verwendung |
| AT402926B (de) * | 1994-12-05 | 1997-09-25 | Hafslund Nycomed Pharma | Heterocyclische amide, verfahren zu ihrer herstellung und verwendung |
| IL117620A0 (en) * | 1995-03-27 | 1996-07-23 | Fujisawa Pharmaceutical Co | Heterocyclic compounds processes for the preparation thereof and pharmaceutical compositions containing the same |
| TW513418B (en) * | 1996-07-31 | 2002-12-11 | Otsuka Pharma Co Ltd | Thiazole derivatives, their production and use |
| US6262096B1 (en) | 1997-11-12 | 2001-07-17 | Bristol-Myers Squibb Company | Aminothiazole inhibitors of cyclin dependent kinases |
| US6214852B1 (en) | 1998-10-21 | 2001-04-10 | Bristol-Myers Squibb Company | N-[5-[[[5-alkyl-2-oxazolyl]methyl]thio]-2-thiazolyl]-carboxamide inhibitors of cyclin dependent kinases |
| US6414156B2 (en) | 1998-10-21 | 2002-07-02 | Bristol-Myers Squibb Company | Process for preparing azacycloalkanoylaminothiazoles |
| GB9823871D0 (en) * | 1998-10-30 | 1998-12-23 | Pharmacia & Upjohn Spa | 2-Amino-thiazole derivatives, process for their preparation, and their use as antitumour agents |
| PT1169038E (pt) | 1999-04-15 | 2012-10-26 | Bristol Myers Squibb Co | Inibidores cíclicos da proteína tirosina cinase |
| US7125875B2 (en) | 1999-04-15 | 2006-10-24 | Bristol-Myers Squibb Company | Cyclic protein tyrosine kinase inhibitors |
| US6392053B2 (en) | 1999-12-15 | 2002-05-21 | Bristol-Myers Squibb Company | Process for preparing arylacetylaminothiazoles |
| US6515004B1 (en) | 1999-12-15 | 2003-02-04 | Bristol-Myers Squibb Company | N-[5-[[[5-alkyl-2-oxazolyl]methyl]thio]-2-thiazolyl]-carboxamide inhibitors of cyclin dependent kinases |
| EP1313729B1 (en) | 2000-08-17 | 2007-03-21 | Lumera Corporation | Design and synthesis of thiophene derived nlo materials for electro-optic applications |
| CA2433018A1 (en) | 2000-12-21 | 2002-06-27 | Joel C. Barrish | Thiazolyl inhibitors of tec family tyrosine kinases |
| EP1724270A3 (en) | 2001-07-19 | 2007-01-03 | Pfizer Italia S.r.l. | Phenylacetamido-thiazole derivatives, process for their preparation and their use as antitumor agents |
| ES2416304T3 (es) | 2002-01-18 | 2013-07-31 | Astellas Pharma Inc. | Derivado de 2-acilaminotiazol o sal del mismo |
| EP1647553A4 (en) | 2003-07-17 | 2008-12-31 | Astellas Pharma Inc | 2-ACYLAMINOTHIAZOL DERIVATIVE OR SALT THEREOF |
| JP4774995B2 (ja) * | 2005-01-12 | 2011-09-21 | アステラス製薬株式会社 | アシルアミノチアゾール誘導体を有効成分とする医薬組成物 |
| US8841334B2 (en) | 2006-05-31 | 2014-09-23 | Abbvie Inc. | Compounds as cannabinoid receptor ligands and uses thereof |
| CA2647598A1 (en) | 2006-05-31 | 2007-12-06 | Abbott Laboratories | Compounds as cannabinoid receptor ligands and uses thereof |
| AU2007266535A1 (en) | 2006-05-31 | 2007-12-06 | Abbott Laboratories | Thiazole compounds as cannabinoid receptor ligands and uses thereof |
| WO2008028094A1 (en) | 2006-08-31 | 2008-03-06 | Abbott Laboratories | Compounds as cb2 cannabinoid receptor ligands |
| WO2008028093A1 (en) | 2006-08-31 | 2008-03-06 | Abbott Laboratories | Compounds as cb2 cannabinoid receptor ligands |
| CN101765594A (zh) | 2007-03-28 | 2010-06-30 | 雅培制药有限公司 | 作为大麻素受体配体的1,3-噻唑-2(3h)-亚基化合物 |
| US7872033B2 (en) | 2007-04-17 | 2011-01-18 | Abbott Laboratories | Compounds as cannabinoid receptor ligands |
| US8735434B2 (en) | 2007-05-18 | 2014-05-27 | Abbvie Inc. | Compounds as cannabinoid receptor ligands |
| US9193713B2 (en) | 2007-10-12 | 2015-11-24 | Abbvie Inc. | Compounds as cannabinoid receptor ligands |
| TWI437986B (zh) * | 2008-01-31 | 2014-05-21 | R Tech Ueno Ltd | 噻唑衍生物及使用該衍生物作為ｖａｐ－１抑制劑之用途 |
| JP2011513495A (ja) | 2008-03-11 | 2011-04-28 | アボット・ラボラトリーズ | カンナビノイド受容体リガンドとしての新規な化合物 |
| US8846730B2 (en) | 2008-09-08 | 2014-09-30 | Abbvie Inc. | Compounds as cannabinoid receptor ligands |
| US8188135B2 (en) | 2008-09-16 | 2012-05-29 | Abbott Laboratories | Compounds as cannabinoid receptor ligands |
| PA8854001A1 (es) | 2008-12-16 | 2010-07-27 | Abbott Lab | Compuestos novedosos como ligandos de receptores de canabinoides |
| CN101768130B (zh) * | 2008-12-30 | 2012-07-04 | 天津药物研究院 | 含氨甲基五元芳香杂环4-羧酸类衍生物、其制备方法和用途 |
| CN101768155B (zh) * | 2008-12-30 | 2012-09-05 | 天津药物研究院 | 一类含(氨甲基-五元芳香杂环-4-羰基)-吡咯烷-2-羧酸的衍生物、其制备方法和用途 |
| CN104151262B (zh) * | 2014-07-07 | 2016-02-24 | 浙江大学 | 4,5-二取代-2-氨基噻唑化合物及其制备方法 |
| CN104163802B (zh) * | 2014-07-08 | 2016-04-27 | 浙江大学 | 2-氨基噻唑-4-甲酸乙酯的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB951885A (en) * | 1961-05-13 | 1964-03-11 | Sankyo Co | A new process for the preparation of thiazole compounds |
| US4649146A (en) * | 1983-01-31 | 1987-03-10 | Fujisawa Pharmaceutical Co., Ltd. | Thiazole derivatives and pharmaceutical composition comprising the same |
-
1990
- 1990-07-16 TW TW079105854A patent/TW205041B/zh active
- 1990-07-19 PH PH40861A patent/PH26766A/en unknown
- 1990-07-23 IE IE267990A patent/IE902679A1/en unknown
- 1990-07-31 DK DK90114628.2T patent/DK0412404T3/da active
- 1990-07-31 AT AT90114628T patent/ATE133667T1/de not_active IP Right Cessation
- 1990-07-31 DE DE69025104T patent/DE69025104T2/de not_active Expired - Fee Related
- 1990-07-31 ES ES90114628T patent/ES2082805T3/es not_active Expired - Lifetime
- 1990-07-31 AU AU60045/90A patent/AU635758B2/en not_active Ceased
- 1990-07-31 EP EP90114628A patent/EP0412404B1/en not_active Expired - Lifetime
- 1990-08-03 IL IL9528190A patent/IL95281A/en not_active IP Right Cessation
- 1990-08-06 HU HU904912A patent/HUT57752A/hu unknown
- 1990-08-06 RU SU904830691A patent/RU2010026C1/ru active
- 1990-08-06 PT PT94925A patent/PT94925B/pt not_active IP Right Cessation
- 1990-08-06 NO NO903438A patent/NO179638C/no unknown
- 1990-08-06 CA CA002022731A patent/CA2022731A1/en not_active Abandoned
- 1990-08-06 JP JP2208833A patent/JPH0368567A/ja active Pending
- 1990-08-06 FI FI903879A patent/FI96857C/fi not_active IP Right Cessation
- 1990-08-06 KR KR1019900012081A patent/KR910004582A/ko not_active Application Discontinuation
- 1990-08-06 CN CN90106739A patent/CN1027370C/zh not_active Expired - Fee Related
-
1991
- 1991-11-22 RU SU915010232A patent/RU2048468C1/ru active
-
1995
- 1995-06-22 HU HU95P/P00375P patent/HU211557A9/hu unknown
-
1996
- 1996-02-15 GR GR960400408T patent/GR3019009T3/el unknown
- 1996-08-08 HK HK151596A patent/HK151596A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0412404A2 (en) | 1991-02-13 |
| PT94925B (pt) | 1997-04-30 |
| CN1049337A (zh) | 1991-02-20 |
| NO903438D0 (no) | 1990-08-06 |
| JPH0368567A (ja) | 1991-03-25 |
| PT94925A (pt) | 1991-04-18 |
| FI903879A0 (fi) | 1990-08-06 |
| HU211557A9 (en) | 1995-12-28 |
| NO179638C (no) | 1996-11-20 |
| DE69025104D1 (de) | 1996-03-14 |
| DE69025104T2 (de) | 1996-07-04 |
| FI96857B (fi) | 1996-05-31 |
| DK0412404T3 (da) | 1996-02-26 |
| CN1027370C (zh) | 1995-01-11 |
| HU904912D0 (en) | 1991-01-28 |
| HUT57752A (en) | 1991-12-30 |
| AU6004590A (en) | 1991-02-07 |
| FI96857C (fi) | 1996-09-10 |
| KR910004582A (ko) | 1991-03-29 |
| AU635758B2 (en) | 1993-04-01 |
| RU2048468C1 (ru) | 1995-11-20 |
| EP0412404A3 (en) | 1991-06-12 |
| ES2082805T3 (es) | 1996-04-01 |
| IL95281A0 (en) | 1991-06-30 |
| IE902679A1 (en) | 1991-02-27 |
| NO903438L (no) | 1991-02-08 |
| HK151596A (en) | 1996-08-16 |
| GR3019009T3 (en) | 1996-05-31 |
| NO179638B (no) | 1996-08-12 |
| ATE133667T1 (de) | 1996-02-15 |
| EP0412404B1 (en) | 1996-01-31 |
| IL95281A (en) | 1996-06-18 |
| CA2022731A1 (en) | 1991-02-08 |
| RU2010026C1 (ru) | 1994-03-30 |
| TW205041B (fi) | 1993-05-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PH26766A (en) | Thiazole derivatives and pharmaceutical composition containing said compound | |
| JP3885116B2 (ja) | 蛋白チロシンキナーゼ媒介細胞増殖を抑制するためのピリド［２，３−ｄ］ピリミジン類 | |
| EP0443568B1 (en) | Fused thiophene derivatives, their production and use | |
| EP0224919B1 (en) | new thiazole compounds, processes for the preparation thereof and pharmaceutical composition comprising the same | |
| US8410282B2 (en) | Compounds as adenosine A1 receptor antagonists | |
| JPH05155871A (ja) | ２−アシルアミノ−５−チアゾール誘導体、製法および組成物 | |
| WO1996030370A2 (en) | Thiazole and thiadiazole derivatives, their preparation and pharmaceutical compositions useful in the treatment of thrombocytopenia | |
| SE445642B (sv) | Antiallergiskt och antiastmatiskt verksamma azolopyrimidinoner samt forfarande for deras framstellning | |
| US5369107A (en) | Thiazole derivatives, processes for production thereof and pharmaceutical compositions comprising the same | |
| IE912073A1 (en) | Pharmaceutical compounds | |
| EP0761658A1 (en) | Azole-phenyl urea derivatives as ACAT inhibitors and their production | |
| JPH11503121A (ja) | アミジン誘導体 | |
| EP0555480A1 (en) | Novel thiazole derivative | |
| EP0032058A1 (en) | Thiazole derivatives, processes for the preparation thereof and pharmaceutical composition comprising the same | |
| US5284661A (en) | Fused thiophene derivatives, their production and use | |
| US5071864A (en) | Aminoalkyl-substituted 2-aminothiazoles and therapeutic agents containing them | |
| JP2531329B2 (ja) | 新規化合物 | |
| HUT71352A (en) | Heterocyclic derivatives | |
| FI60011B (fi) | Foerfarande foer framstaellning av antiflogistiska och blodplaettars aggregering haemmande 4-hydroxi-2h-nafto/2,1-e/-tiazin-3-karboxamid-1,1-dioxider | |
| SU1042620A3 (ru) | Способ получени замещенных N-(5-тетразолил)-1-кето-1- @ -тиазол(3,2- @ )пиримидин-2-карбоксамидов или их солей и его вариант | |
| EP0397169B1 (en) | Novel benzothiazole derivatives | |
| KR860000106B1 (ko) | 피리미딘 유도체의 제조방법 | |
| JPH05112559A (ja) | ４−アミノ−５−ピリミジンカルボン酸誘導体 | |
| JPH09295974A (ja) | アゾール誘導体、その用途及びその製造方法並びにその使用方法 | |
| JPS5951544B2 (ja) | チアジン誘導体 |