HRP980645A2 - Thiazole derivatives - Google Patents

Thiazole derivatives Download PDF

Info

Publication number: HRP980645A2
Authority: HR; Croatia
Prior art keywords: amino; phenyl; thiazole; carbonyl; methyl
Prior art date: 1998-01-02

Application number

HR98100006.0A

Other languages

English (en)

Croatian (hr)

Inventor

Thomas Weller

Original Assignee

Hoffmann La Roche

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-01-02

Filing date

1998-12-29

Publication date

1999-10-31

1998-12-29 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1999-10-31 Publication of HRP980645A2 publication Critical patent/HRP980645A2/hr

Links

150000007979 thiazole derivatives Chemical class 0.000 title description 5
-1 alkyl-O-CO- Chemical group 0.000 claims description 230
150000001875 compounds Chemical class 0.000 claims description 174
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 102
238000000034 method Methods 0.000 claims description 98
239000001257 hydrogen Substances 0.000 claims description 64
229910052739 hydrogen Inorganic materials 0.000 claims description 64
125000000217 alkyl group Chemical group 0.000 claims description 61
150000002148 esters Chemical class 0.000 claims description 50
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 44
125000000753 cycloalkyl group Chemical group 0.000 claims description 33
125000001424 substituent group Chemical group 0.000 claims description 30
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 25
238000006243 chemical reaction Methods 0.000 claims description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
150000001412 amines Chemical class 0.000 claims description 23
125000003710 aryl alkyl group Chemical group 0.000 claims description 22
125000003545 alkoxy group Chemical group 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 21
206010028980 Neoplasm Diseases 0.000 claims description 20
229910052736 halogen Inorganic materials 0.000 claims description 20
150000002367 halogens Chemical group 0.000 claims description 19
238000011321 prophylaxis Methods 0.000 claims description 19
125000003118 aryl group Chemical group 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
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102100022337 Integrin alpha-V Human genes 0.000 claims description 17
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
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150000001370 alpha-amino acid derivatives Chemical group 0.000 claims description 5
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 5
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QDGAVODICPCDMU-UHFFFAOYSA-N 2-amino-3-[3-[bis(2-chloroethyl)amino]phenyl]propanoic acid Chemical group OC(=O)C(N)CC1=CC=CC(N(CCCl)CCCl)=C1 QDGAVODICPCDMU-UHFFFAOYSA-N 0.000 claims description 4
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AUVANWMAELELBU-UHFFFAOYSA-N ethyl 3-[3-[[2-(diaminomethylideneamino)-1,3-thiazole-4-carbonyl]amino]propanoylamino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CCNC(=O)C1=CSC(NC(N)=N)=N1 AUVANWMAELELBU-UHFFFAOYSA-N 0.000 description 3
WUQOWMVMOZXSFC-UHFFFAOYSA-N ethyl 3-[3-[[2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carbonyl]amino]propanoylamino]propanoate Chemical compound CCOC(=O)CCNC(=O)CCNC(=O)C=1SC(NC(N)=N)=NC=1C WUQOWMVMOZXSFC-UHFFFAOYSA-N 0.000 description 3
SEBKZAJINKUAOT-UHFFFAOYSA-N ethyl 3-[[2-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-3-pyridin-3-ylpropanoate Chemical compound C=1C=CN=CC=1C(CC(=O)OCC)NC(=O)CNC(=O)C(N=1)=CSC=1NC(=O)NCC1=CC=CC=C1 SEBKZAJINKUAOT-UHFFFAOYSA-N 0.000 description 3
ZZNPSQNHIMITTK-UHFFFAOYSA-N ethyl 3-[[2-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]propanoate Chemical compound CCOC(=O)CCNC(=O)CNC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 ZZNPSQNHIMITTK-UHFFFAOYSA-N 0.000 description 3
KQWWVLVLVYYYDT-UHFFFAOYSA-N ethyl 3-oxohexanoate Chemical compound CCCC(=O)CC(=O)OCC KQWWVLVLVYYYDT-UHFFFAOYSA-N 0.000 description 3
RUUIDGWMIRMESR-UHFFFAOYSA-N ethyl 6-amino-3-phenylhexanoate;hydrochloride Chemical compound Cl.CCOC(=O)CC(CCCN)C1=CC=CC=C1 RUUIDGWMIRMESR-UHFFFAOYSA-N 0.000 description 3
238000004108 freeze drying Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
230000008611 intercellular interaction Effects 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
239000012948 isocyanate Substances 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
125000006501 nitrophenyl group Chemical group 0.000 description 3
BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
210000002826 placenta Anatomy 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000002464 receptor antagonist Substances 0.000 description 3
229940044551 receptor antagonist Drugs 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000011877 solvent mixture Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 2
CPVUCJNHCBIRME-AXDSSHIGSA-N (2s)-2-[3-[[2-[[2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carbonyl]amino]acetyl]amino]-4-oxopiperidin-1-yl]butanoic acid Chemical compound C1N([C@@H](CC)C(O)=O)CCC(=O)C1NC(=O)CNC(=O)C1=C(C)N=C(NC(N)=N)S1 CPVUCJNHCBIRME-AXDSSHIGSA-N 0.000 description 2
AKZXPYXTNXTEIN-NSHDSACASA-N (2s)-2-[[2-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NC(=O)CNC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 AKZXPYXTNXTEIN-NSHDSACASA-N 0.000 description 2
AGIHLPSIUJXHTC-SFHVURJKSA-N (3s)-3-[[2-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-4-(3-methoxyanilino)-4-oxobutanoic acid Chemical compound COC1=CC=CC(NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)C=2N=C(NC(=O)NCC=3C=CC=CC=3)SC=2)=C1 AGIHLPSIUJXHTC-SFHVURJKSA-N 0.000 description 2
DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical group C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
ZTTOLMMWPFRFBL-UHFFFAOYSA-N 1-[5-(3-aminophenyl)-4-methyl-1,3-thiazol-2-yl]-3-benzylurea Chemical compound S1C(C=2C=C(N)C=CC=2)=C(C)N=C1NC(=O)NCC1=CC=CC=C1 ZTTOLMMWPFRFBL-UHFFFAOYSA-N 0.000 description 2
KSKLHQQKAFMWSA-VOTSOKGWSA-N 1-nitro-4-[(e)-2-nitroprop-1-enyl]benzene Chemical compound [O-][N+](=O)C(/C)=C/C1=CC=C([N+]([O-])=O)C=C1 KSKLHQQKAFMWSA-VOTSOKGWSA-N 0.000 description 2
FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 2
KZUWZSWBLZKXCW-UHFFFAOYSA-N 2-(diaminomethylideneamino)-1,3-thiazole-4-carboxylic acid;hydrate Chemical compound O.NC(=N)NC1=NC(C(O)=O)=CS1 KZUWZSWBLZKXCW-UHFFFAOYSA-N 0.000 description 2
IRZHUMRBBAVGOA-UHFFFAOYSA-N 2-(diaminomethylideneamino)-4-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound S1C(NC(=N)N)=NC(C=2C=CC=CC=2)=C1C(O)=O IRZHUMRBBAVGOA-UHFFFAOYSA-N 0.000 description 2
RLWFSZLVYWBFLQ-UHFFFAOYSA-N 2-(diaminomethylideneamino)-4-propyl-1,3-thiazole-5-carboxylic acid;hydrochloride Chemical compound Cl.CCCC=1N=C(NC(N)=N)SC=1C(O)=O RLWFSZLVYWBFLQ-UHFFFAOYSA-N 0.000 description 2
WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 2
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 2
GESCRYMIVGRTSQ-UHFFFAOYSA-N 2-[4-methyl-5-(3-nitrophenyl)-1,3-thiazol-2-yl]guanidine Chemical compound N1=C(NC(N)=N)SC(C=2C=C(C=CC=2)[N+]([O-])=O)=C1C GESCRYMIVGRTSQ-UHFFFAOYSA-N 0.000 description 2
KGWAMNLTYBAKKR-UHFFFAOYSA-N 2-[4-methyl-5-(4-nitrophenyl)-1,3-thiazol-2-yl]guanidine Chemical compound N1=C(NC(N)=N)SC(C=2C=CC(=CC=2)[N+]([O-])=O)=C1C KGWAMNLTYBAKKR-UHFFFAOYSA-N 0.000 description 2
JJHQIPNHNMSMHY-UHFFFAOYSA-N 2-[5-(3-nitrophenyl)-4-pentyl-1,3-thiazol-2-yl]guanidine Chemical compound N1=C(NC(N)=N)SC(C=2C=C(C=CC=2)[N+]([O-])=O)=C1CCCCC JJHQIPNHNMSMHY-UHFFFAOYSA-N 0.000 description 2
CAEJWTVYERMTKE-UHFFFAOYSA-N 2-[5-(4-aminophenyl)-4-methyl-1,3-thiazol-2-yl]guanidine;hydrochloride Chemical compound Cl.N1=C(NC(N)=N)SC(C=2C=CC(N)=CC=2)=C1C CAEJWTVYERMTKE-UHFFFAOYSA-N 0.000 description 2
CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
MXALCEDZNIXINZ-UHFFFAOYSA-N 3-(3-bromophenyl)-5-[3-[2-(diaminomethylideneamino)-4-methyl-1,3-thiazol-5-yl]anilino]-5-oxopentanoic acid Chemical compound N1=C(NC(N)=N)SC(C=2C=C(NC(=O)CC(CC(O)=O)C=3C=C(Br)C=CC=3)C=CC=2)=C1C MXALCEDZNIXINZ-UHFFFAOYSA-N 0.000 description 2
SOXXOBPEIHYWML-UHFFFAOYSA-N 3-(4-chlorophenyl)-4-[[3-[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]benzoyl]amino]butanoic acid Chemical compound S1C(NC(=N)N)=NC(C=2C=C(C=CC=2)C(=O)NCC(CC(O)=O)C=2C=CC(Cl)=CC=2)=C1 SOXXOBPEIHYWML-UHFFFAOYSA-N 0.000 description 2
MQNOBLNURKSHLO-UHFFFAOYSA-N 3-(4-chlorophenyl)-4-[[4-[2-(diaminomethylideneamino)-4-methyl-1,3-thiazol-5-yl]benzoyl]amino]butanoic acid Chemical compound N1=C(NC(N)=N)SC(C=2C=CC(=CC=2)C(=O)NCC(CC(O)=O)C=2C=CC(Cl)=CC=2)=C1C MQNOBLNURKSHLO-UHFFFAOYSA-N 0.000 description 2
OICULAYEQLSDJL-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-[3-[2-(diaminomethylideneamino)-4-methyl-1,3-thiazol-5-yl]anilino]-5-oxopentanoic acid Chemical compound N1=C(NC(N)=N)SC(C=2C=C(NC(=O)CC(CC(O)=O)C=3C=CC(Cl)=CC=3)C=CC=2)=C1C OICULAYEQLSDJL-UHFFFAOYSA-N 0.000 description 2
NJENIZRAKPLSLH-UHFFFAOYSA-N 3-(benzylcarbamoyl)-6-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]hexanoic acid Chemical compound C=1C=CC=CC=1CNC(=O)C(CC(=O)O)CCCNC(=O)C(N=1)=CSC=1NC(=O)NCC1=CC=CC=C1 NJENIZRAKPLSLH-UHFFFAOYSA-N 0.000 description 2
NDBROMODXPTBHM-UHFFFAOYSA-N 3-[(3-nitrophenyl)sulfonylamino]-3-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(CC(=O)O)NS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 NDBROMODXPTBHM-UHFFFAOYSA-N 0.000 description 2
QSYRZEDXNGNAEV-UHFFFAOYSA-N 3-[2-(diaminomethylideneamino)-4-methyl-1,3-thiazol-5-yl]benzoic acid Chemical compound N1=C(NC(N)=N)SC(C=2C=C(C=CC=2)C(O)=O)=C1C QSYRZEDXNGNAEV-UHFFFAOYSA-N 0.000 description 2
HGFXIRVZLZCCMN-UHFFFAOYSA-N 3-[3-[[2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carbonyl]amino]propanoylamino]propanoic acid;hydrochloride Chemical compound Cl.CC=1N=C(NC(N)=N)SC=1C(=O)NCCC(=O)NCCC(O)=O HGFXIRVZLZCCMN-UHFFFAOYSA-N 0.000 description 2
RZUFNLWRYJVCDX-UHFFFAOYSA-N 3-[4-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]phenyl]-3-(butylsulfonylamino)propanoic acid Chemical compound C1=CC(C(CC(O)=O)NS(=O)(=O)CCCC)=CC=C1NC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 RZUFNLWRYJVCDX-UHFFFAOYSA-N 0.000 description 2
WZXKUMRRXWYQQN-UHFFFAOYSA-N 3-[[2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carbonyl]amino]benzoic acid Chemical compound N1=C(NC(N)=N)SC(C(=O)NC=2C=C(C=CC=2)C(O)=O)=C1C WZXKUMRRXWYQQN-UHFFFAOYSA-N 0.000 description 2
TVVKELLZNMVCFD-UHFFFAOYSA-N 3-[[2-[[2-(4,5-dihydro-1h-imidazol-2-ylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-3-pyridin-3-ylpropanoic acid;hydrochloride Chemical compound Cl.C=1C=CN=CC=1C(CC(=O)O)NC(=O)CNC(=O)C(N=1)=CSC=1N=C1NCCN1 TVVKELLZNMVCFD-UHFFFAOYSA-N 0.000 description 2
IRLFVURPOSATGF-UHFFFAOYSA-N 3-[[2-[[2-(aminomethyl)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-3-phenylpropanoic acid;hydrochloride Chemical compound Cl.S1C(CN)=NC(C(=O)NCC(=O)NC(CC(O)=O)C=2C=CC=CC=2)=C1 IRLFVURPOSATGF-UHFFFAOYSA-N 0.000 description 2
UOHGGUPPYZIUOI-UHFFFAOYSA-N 3-[[2-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]propanoic acid Chemical compound OC(=O)CCNC(=O)CNC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 UOHGGUPPYZIUOI-UHFFFAOYSA-N 0.000 description 2
YIHSCCAMUMKRDW-UHFFFAOYSA-N 3-[[2-[[2-(benzylcarbamoylamino)-5-methyl-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-3-phenylpropanoic acid Chemical compound N=1C(C(=O)NCC(=O)NC(CC(O)=O)C=2C=CC=CC=2)=C(C)SC=1NC(=O)NCC1=CC=CC=C1 YIHSCCAMUMKRDW-UHFFFAOYSA-N 0.000 description 2
DQNRDOUHLWZVGP-UHFFFAOYSA-N 3-[[2-[[2-(benzylcarbamoylamino)-5-phenyl-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-3-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(CC(=O)O)NC(=O)CNC(=O)C(=C(S1)C=2C=CC=CC=2)N=C1NC(=O)NCC1=CC=CC=C1 DQNRDOUHLWZVGP-UHFFFAOYSA-N 0.000 description 2
IKQVWQQLUPNCGF-UHFFFAOYSA-N 3-[[2-[[2-(diaminomethylideneamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-3-phenylpropanoic acid Chemical compound S1C(NC(=N)N)=NC(C(=O)NCC(=O)NC(CC(O)=O)C=2C=CC=CC=2)=C1 IKQVWQQLUPNCGF-UHFFFAOYSA-N 0.000 description 2
VPOYANXPTLRJKA-UHFFFAOYSA-N 3-[[2-[[2-(diaminomethylideneamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]propanoic acid Chemical compound NC(=N)NC1=NC(C(=O)NCC(=O)NCCC(O)=O)=CS1 VPOYANXPTLRJKA-UHFFFAOYSA-N 0.000 description 2
WVKRECUEKCTMBV-UHFFFAOYSA-N 3-[[2-[[2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carbonyl]amino]acetyl]amino]-3-phenylpropanoic acid;hydrochloride Chemical compound Cl.N1=C(N=C(N)N)SC(C(=O)NCC(=O)NC(CC(O)=O)C=2C=CC=CC=2)=C1C WVKRECUEKCTMBV-UHFFFAOYSA-N 0.000 description 2
OWIFJBJFQNXCDB-UHFFFAOYSA-N 3-[[2-[[2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carbonyl]amino]acetyl]amino]propanoic acid Chemical compound CC=1N=C(NC(N)=N)SC=1C(=O)NCC(=O)NCCC(O)=O OWIFJBJFQNXCDB-UHFFFAOYSA-N 0.000 description 2
PUOVBSYIBMCLRU-UHFFFAOYSA-N 3-[[2-[[2-(diaminomethylideneamino)-5-methyl-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-3-phenylpropanoic acid Chemical compound S1C(NC(N)=N)=NC(C(=O)NCC(=O)NC(CC(O)=O)C=2C=CC=CC=2)=C1C PUOVBSYIBMCLRU-UHFFFAOYSA-N 0.000 description 2
XVGBXCSFDUPSJN-UHFFFAOYSA-N 3-[[2-[cyclopropyl-[2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carbonyl]amino]acetyl]amino]-3-phenylpropanoic acid Chemical compound N1=C(NC(N)=N)SC(C(=O)N(CC(=O)NC(CC(O)=O)C=2C=CC=CC=2)C2CC2)=C1C XVGBXCSFDUPSJN-UHFFFAOYSA-N 0.000 description 2
SBSOZVYLFZMSCB-UHFFFAOYSA-N 3-[[3-[2-(diaminomethylideneamino)-4-methyl-1,3-thiazol-5-yl]phenyl]carbamoylamino]-3-phenylpropanoic acid Chemical compound N1=C(NC(N)=N)SC(C=2C=C(NC(=O)NC(CC(O)=O)C=3C=CC=CC=3)C=CC=2)=C1C SBSOZVYLFZMSCB-UHFFFAOYSA-N 0.000 description 2
BHFOOSJXWACGEV-UHFFFAOYSA-N 3-[[3-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]benzoyl]amino]propanoic acid Chemical compound OC(=O)CCNC(=O)C1=CC=CC(NC(=O)C=2N=C(NC(=O)NCC=3C=CC=CC=3)SC=2)=C1 BHFOOSJXWACGEV-UHFFFAOYSA-N 0.000 description 2
XEGOANUSJSYKIF-UHFFFAOYSA-N 3-[[3-[[2-(diaminomethylideneamino)-1,3-thiazole-4-carbonyl]amino]benzoyl]amino]-3-phenylpropanoic acid Chemical compound S1C(NC(=N)N)=NC(C(=O)NC=2C=C(C=CC=2)C(=O)NC(CC(O)=O)C=2C=CC=CC=2)=C1 XEGOANUSJSYKIF-UHFFFAOYSA-N 0.000 description 2
CDUDBPWVBYOVMQ-UHFFFAOYSA-N 3-[[3-[[2-(diaminomethylideneamino)-1,3-thiazole-4-carbonyl]amino]benzoyl]amino]propanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.S1C(N=C(N)N)=NC(C(=O)NC=2C=C(C=CC=2)C(=O)NCCC(O)=O)=C1 CDUDBPWVBYOVMQ-UHFFFAOYSA-N 0.000 description 2
BQTKMPKZIRIHEJ-UHFFFAOYSA-N 3-[[3-[[2-(diaminomethylideneamino)-1,3-thiazole-5-carbonyl]amino]benzoyl]amino]-3-phenylpropanoic acid Chemical compound S1C(NC(=N)N)=NC=C1C(=O)NC1=CC=CC(C(=O)NC(CC(O)=O)C=2C=CC=CC=2)=C1 BQTKMPKZIRIHEJ-UHFFFAOYSA-N 0.000 description 2
RCNDZQHVHPCCAS-UHFFFAOYSA-N 3-[[3-[[2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carbonyl]amino]-4-methoxybenzoyl]amino]-3-phenylpropanoic acid;hydrochloride Chemical compound Cl.COC1=CC=C(C(=O)NC(CC(O)=O)C=2C=CC=CC=2)C=C1NC(=O)C=1SC(NC(N)=N)=NC=1C RCNDZQHVHPCCAS-UHFFFAOYSA-N 0.000 description 2
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ICBMPFRCOMEPKL-UHFFFAOYSA-N 3-[[3-[[4-methyl-2-(methylcarbamoylamino)-1,3-thiazole-5-carbonyl]amino]benzoyl]amino]-3-pyridin-3-ylpropanoic acid Chemical compound S1C(NC(=O)NC)=NC(C)=C1C(=O)NC1=CC=CC(C(=O)NC(CC(O)=O)C=2C=NC=CC=2)=C1 ICBMPFRCOMEPKL-UHFFFAOYSA-N 0.000 description 2
PUCQXGRPPOEIAH-UHFFFAOYSA-N 3-amino-3-[4-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]phenyl]propanoic acid Chemical compound C1=CC(C(CC(O)=O)N)=CC=C1NC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 PUCQXGRPPOEIAH-UHFFFAOYSA-N 0.000 description 2
QPEJHSFTZVMSJH-UHFFFAOYSA-N 3-amino-5-hydroxybenzoic acid Chemical compound NC1=CC(O)=CC(C(O)=O)=C1 QPEJHSFTZVMSJH-UHFFFAOYSA-N 0.000 description 2
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 2
RHVPXMYSDUMWCV-UHFFFAOYSA-N 3-phenyl-3-[[2-[[2-(2-phenylethylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]propanoic acid Chemical compound C=1C=CC=CC=1C(CC(=O)O)NC(=O)CNC(=O)C(N=1)=CSC=1NC(=O)NCCC1=CC=CC=C1 RHVPXMYSDUMWCV-UHFFFAOYSA-N 0.000 description 2
ISYSZVJGTADPKE-UHFFFAOYSA-N 3-phenyl-3-[[2-[[2-(phenylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]propanoic acid Chemical compound C=1C=CC=CC=1C(CC(=O)O)NC(=O)CNC(=O)C(N=1)=CSC=1NC(=O)NC1=CC=CC=C1 ISYSZVJGTADPKE-UHFFFAOYSA-N 0.000 description 2
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DSPQPSYCMIMDRI-UHFFFAOYSA-N diethyl 2-(3-azido-2-oxopropyl)butanedioate Chemical compound CCOC(=O)CC(C(=O)OCC)CC(=O)CN=[N+]=[N-] DSPQPSYCMIMDRI-UHFFFAOYSA-N 0.000 description 2
KDYGRRJEHAZMTH-UHFFFAOYSA-N diethyl 2-(3-bromo-2-oxopropyl)butanedioate Chemical compound CCOC(=O)CC(CC(=O)CBr)C(=O)OCC KDYGRRJEHAZMTH-UHFFFAOYSA-N 0.000 description 2
XNFJIAUTENROSE-UHFFFAOYSA-N diethyl 2-[3-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]-2-oxopropyl]butanedioate Chemical compound CCOC(=O)CC(C(=O)OCC)CC(=O)CNC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 XNFJIAUTENROSE-UHFFFAOYSA-N 0.000 description 2
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QGHZWHGVXLIALP-UHFFFAOYSA-N ethyl 2-(diaminomethylideneamino)-4-phenyl-1,3-thiazole-5-carboxylate;hydrobromide Chemical compound Br.S1C(NC(N)=N)=NC(C=2C=CC=CC=2)=C1C(=O)OCC QGHZWHGVXLIALP-UHFFFAOYSA-N 0.000 description 2
FUIRJYVCEQYVMH-UHFFFAOYSA-N ethyl 2-(diaminomethylideneamino)-4-propyl-1,3-thiazole-5-carboxylate;hydrobromide Chemical compound Br.CCCC=1N=C(NC(N)=N)SC=1C(=O)OCC FUIRJYVCEQYVMH-UHFFFAOYSA-N 0.000 description 2
JJMPHQKGNFNAEJ-UHFFFAOYSA-N ethyl 2-(pyridin-2-ylmethylcarbamoylamino)-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(NC(=O)NCC=2N=CC=CC=2)=N1 JJMPHQKGNFNAEJ-UHFFFAOYSA-N 0.000 description 2
RAZNNERIXCQWAK-UHFFFAOYSA-N ethyl 2-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]acetate Chemical compound CCOC(=O)CNC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 RAZNNERIXCQWAK-UHFFFAOYSA-N 0.000 description 2
QSOBILXJDUDYOI-UHFFFAOYSA-N ethyl 2-[[2-(diaminomethylideneamino)-1,3-thiazole-4-carbonyl]amino]acetate Chemical compound CCOC(=O)CNC(=O)C1=CSC(NC(N)=N)=N1 QSOBILXJDUDYOI-UHFFFAOYSA-N 0.000 description 2
WZHUPCREDVWLKC-UHFFFAOYSA-N ethyl 2-amino-4-methyl-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N)=NC=1C WZHUPCREDVWLKC-UHFFFAOYSA-N 0.000 description 2
VQVSVDPSZLALAR-UHFFFAOYSA-N ethyl 3-[(3-amino-4-methoxybenzoyl)amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)C1=CC=C(OC)C(N)=C1 VQVSVDPSZLALAR-UHFFFAOYSA-N 0.000 description 2
VSTKLGKQQSVKBV-UHFFFAOYSA-N ethyl 3-[4-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OCC)=CC=C1NC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 VSTKLGKQQSVKBV-UHFFFAOYSA-N 0.000 description 2
VWLHAXXQRUHAGI-UHFFFAOYSA-N ethyl 3-[[2-[[2-(4,5-dihydro-1h-imidazol-2-ylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-3-pyridin-3-ylpropanoate Chemical compound C=1C=CN=CC=1C(CC(=O)OCC)NC(=O)CNC(=O)C(N=1)=CSC=1N=C1NCCN1 VWLHAXXQRUHAGI-UHFFFAOYSA-N 0.000 description 2
UNTGBSIBMLUOJT-UHFFFAOYSA-N ethyl 3-[[2-[[2-(benzylcarbamoylamino)-5-methyl-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CNC(=O)C(=C(S1)C)N=C1NC(=O)NCC1=CC=CC=C1 UNTGBSIBMLUOJT-UHFFFAOYSA-N 0.000 description 2
OKDGEWZVSODHBT-UHFFFAOYSA-N ethyl 3-[[2-[[2-(benzylcarbamoylamino)-5-phenyl-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CNC(=O)C(=C(S1)C=2C=CC=CC=2)N=C1NC(=O)NCC1=CC=CC=C1 OKDGEWZVSODHBT-UHFFFAOYSA-N 0.000 description 2
FUIWVGYYUHLXKX-UHFFFAOYSA-N ethyl 3-[[2-[[2-(butylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-3-phenylpropanoate Chemical compound S1C(NC(=O)NCCCC)=NC(C(=O)NCC(=O)NC(CC(=O)OCC)C=2C=CC=CC=2)=C1 FUIWVGYYUHLXKX-UHFFFAOYSA-N 0.000 description 2
APEVNZFNQCVULB-UHFFFAOYSA-N ethyl 3-[[2-[[2-(diaminomethylideneamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]propanoate Chemical compound CCOC(=O)CCNC(=O)CNC(=O)C1=CSC(NC(N)=N)=N1 APEVNZFNQCVULB-UHFFFAOYSA-N 0.000 description 2
NUQOJDMPHAHUDE-UHFFFAOYSA-N ethyl 3-[[3-[2-(diaminomethylideneamino)-4-methyl-1,3-thiazol-5-yl]phenyl]carbamoylamino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)NC(C=1)=CC=CC=1C=1SC(NC(N)=N)=NC=1C NUQOJDMPHAHUDE-UHFFFAOYSA-N 0.000 description 2
XPGDTTHMZKFRLK-UHFFFAOYSA-N ethyl 3-[[3-[[2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carbonyl]amino]-4-methoxybenzoyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)C(C=1)=CC=C(OC)C=1NC(=O)C=1SC(NC(N)=N)=NC=1C XPGDTTHMZKFRLK-UHFFFAOYSA-N 0.000 description 2
DZWWOPIZZZYBMK-UHFFFAOYSA-N ethyl 3-[[3-[[2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carbonyl]amino]-5-phenylmethoxybenzoyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)C(C=C(OCC=1C=CC=CC=1)C=1)=CC=1NC(=O)C=1SC(NC(N)=N)=NC=1C DZWWOPIZZZYBMK-UHFFFAOYSA-N 0.000 description 2
PNYRHDQKDJXHKL-UHFFFAOYSA-N ethyl 3-[[3-[[2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carbonyl]amino]benzoyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)C(C=1)=CC=CC=1NC(=O)C=1SC(NC(N)=N)=NC=1C PNYRHDQKDJXHKL-UHFFFAOYSA-N 0.000 description 2
OHXQJZIBASKGJY-UHFFFAOYSA-N ethyl 3-amino-3-pyridin-3-ylpropanoate;hydrochloride Chemical compound Cl.CCOC(=O)CC(N)C1=CC=CN=C1 OHXQJZIBASKGJY-UHFFFAOYSA-N 0.000 description 2
OHKUPVSLSSODPK-UHFFFAOYSA-N ethyl 3-phenyl-3-[[2-[[2-(2-phenylethylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]propanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CNC(=O)C(N=1)=CSC=1NC(=O)NCCC1=CC=CC=C1 OHKUPVSLSSODPK-UHFFFAOYSA-N 0.000 description 2
NXCIRGCOCWVPNI-UHFFFAOYSA-N ethyl 3-phenyl-3-[[2-[[2-(phenylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]propanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CNC(=O)C(N=1)=CSC=1NC(=O)NC1=CC=CC=C1 NXCIRGCOCWVPNI-UHFFFAOYSA-N 0.000 description 2
VUYNTIDSHCJIKF-UHFFFAOYSA-N ethyl 4,4-dimethyl-3-oxopentanoate Chemical compound CCOC(=O)CC(=O)C(C)(C)C VUYNTIDSHCJIKF-UHFFFAOYSA-N 0.000 description 2
VNUOWLZIQBNXQW-UHFFFAOYSA-N ethyl 4-cyclopentyl-2-(diaminomethylideneamino)-1,3-thiazole-5-carboxylate;hydrobromide Chemical compound Br.S1C(NC(N)=N)=NC(C2CCCC2)=C1C(=O)OCC VNUOWLZIQBNXQW-UHFFFAOYSA-N 0.000 description 2
AFIBNEJBLRTYBI-UHFFFAOYSA-N ethyl 4-methyl-2-(methylcarbamoylamino)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(NC(=O)NC)=NC=1C AFIBNEJBLRTYBI-UHFFFAOYSA-N 0.000 description 2
KTOHWXGEDHQJKZ-UHFFFAOYSA-N ethyl 6-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]-3-phenylhexanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)CCCNC(=O)C(N=1)=CSC=1NC(=O)NCC1=CC=CC=C1 KTOHWXGEDHQJKZ-UHFFFAOYSA-N 0.000 description 2
HYRBHZVUVJHQHT-UHFFFAOYSA-N ethyl 6-[[2-(diaminomethylideneamino)-1,3-thiazole-4-carbonyl]amino]-3-phenylhexanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)CCCNC(=O)C1=CSC(NC(N)=N)=N1 HYRBHZVUVJHQHT-UHFFFAOYSA-N 0.000 description 2
WTNNCKXVWCKEOY-UHFFFAOYSA-N ethyl 6-amino-3-(benzylcarbamoyl)hexanoate;hydrochloride Chemical compound Cl.CCOC(=O)CC(CCCN)C(=O)NCC1=CC=CC=C1 WTNNCKXVWCKEOY-UHFFFAOYSA-N 0.000 description 2
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NRCGBQGWJVCFKA-UHFFFAOYSA-N ethyl 7-[[2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carbonyl]amino]-3-phenylheptanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)CCCCNC(=O)C=1SC(NC(N)=N)=NC=1C NRCGBQGWJVCFKA-UHFFFAOYSA-N 0.000 description 2
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KENWYBHLJTVSSQ-UHFFFAOYSA-N methyl 6-[3-[2-(diaminomethylideneamino)-4-methyl-1,3-thiazol-5-yl]anilino]-6-oxohexanoate Chemical compound COC(=O)CCCCC(=O)NC1=CC=CC(C2=C(N=C(NC(N)=N)S2)C)=C1 KENWYBHLJTVSSQ-UHFFFAOYSA-N 0.000 description 2
CMZYXUJPIPZCBS-UHFFFAOYSA-N methyl 6-[4-[2-(diaminomethylideneamino)-4-methyl-1,3-thiazol-5-yl]anilino]-6-oxohexanoate Chemical compound C1=CC(NC(=O)CCCCC(=O)OC)=CC=C1C1=C(C)N=C(NC(N)=N)S1 CMZYXUJPIPZCBS-UHFFFAOYSA-N 0.000 description 2
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239000000975 dye Substances 0.000 description 1
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
OCLXJTCGWSSVOE-UHFFFAOYSA-N ethanol etoh Chemical compound CCO.CCO OCLXJTCGWSSVOE-UHFFFAOYSA-N 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
PKBGMHHQJHFTGT-UHFFFAOYSA-N ethyl 2-(4,5-dihydro-1h-imidazol-2-ylamino)-1,3-thiazole-4-carboxylate;hydrobromide Chemical compound Br.CCOC(=O)C1=CSC(N=C2NCCN2)=N1 PKBGMHHQJHFTGT-UHFFFAOYSA-N 0.000 description 1
RZQDWFWACMUXFR-UHFFFAOYSA-N ethyl 2-(benzylcarbamoylamino)-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 RZQDWFWACMUXFR-UHFFFAOYSA-N 0.000 description 1
GHDUSFQFGFGLRA-UHFFFAOYSA-N ethyl 2-(benzylcarbamoylamino)-1,3-thiazole-5-carboxylate Chemical compound C(C1=CC=CC=C1)NC(NC=1SC(=CN=1)C(=O)OCC)=O GHDUSFQFGFGLRA-UHFFFAOYSA-N 0.000 description 1
VPMRGFCOSZORMN-UHFFFAOYSA-N ethyl 2-(benzylcarbamoylamino)-4-methyl-1,3-thiazole-5-carboxylate Chemical compound CC1=C(C(=O)OCC)SC(NC(=O)NCC=2C=CC=CC=2)=N1 VPMRGFCOSZORMN-UHFFFAOYSA-N 0.000 description 1
LBSBQVAGEVSBQP-UHFFFAOYSA-N ethyl 2-(diaminomethylideneamino)-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(N=C(N)N)=N1 LBSBQVAGEVSBQP-UHFFFAOYSA-N 0.000 description 1
LIBLLNBLKAGOQW-UHFFFAOYSA-N ethyl 2-(diaminomethylideneamino)-1,3-thiazole-4-carboxylate;hydrobromide Chemical compound Br.CCOC(=O)C1=CSC(NC(N)=N)=N1 LIBLLNBLKAGOQW-UHFFFAOYSA-N 0.000 description 1
IIZWYNDWOXSKNC-UHFFFAOYSA-N ethyl 2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C=1SC(NC(N)=N)=NC=1C IIZWYNDWOXSKNC-UHFFFAOYSA-N 0.000 description 1
IDFOGVMOZOTGAT-UHFFFAOYSA-N ethyl 2-(phenoxycarbonylamino)-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(NC(=O)OC=2C=CC=CC=2)=N1 IDFOGVMOZOTGAT-UHFFFAOYSA-N 0.000 description 1
OJLOWWJZAOEGDR-UHFFFAOYSA-N ethyl 2-(pyridin-2-ylamino)-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(NC=2N=CC=CC=2)=N1 OJLOWWJZAOEGDR-UHFFFAOYSA-N 0.000 description 1
RDULEYWUGKOCMR-UHFFFAOYSA-N ethyl 2-chloro-3-oxobutanoate Chemical compound CCOC(=O)C(Cl)C(C)=O RDULEYWUGKOCMR-UHFFFAOYSA-N 0.000 description 1
OKOLWYZIKJHXIH-UHFFFAOYSA-N ethyl 3-(3-aminopropanoylamino)propanoate;hydrochloride Chemical compound Cl.CCOC(=O)CCNC(=O)CCN OKOLWYZIKJHXIH-UHFFFAOYSA-N 0.000 description 1
PTABRRLBRPELAW-UHFFFAOYSA-N ethyl 3-(4-aminophenyl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound CCOC(=O)CC(NC(=O)OC(C)(C)C)C1=CC=C(N)C=C1 PTABRRLBRPELAW-UHFFFAOYSA-N 0.000 description 1
RZBSJOJRYOOOBI-UHFFFAOYSA-N ethyl 3-[(2-aminoacetyl)amino]-3-pyridin-3-ylpropanoate;hydrochloride Chemical compound Cl.CCOC(=O)CC(NC(=O)CN)C1=CC=CN=C1 RZBSJOJRYOOOBI-UHFFFAOYSA-N 0.000 description 1
BWLGVFDSSAHWTK-UHFFFAOYSA-N ethyl 3-[(3-aminophenyl)sulfonylamino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NS(=O)(=O)C1=CC=CC(N)=C1 BWLGVFDSSAHWTK-UHFFFAOYSA-N 0.000 description 1
BZTPNTVTJQTRRS-UHFFFAOYSA-N ethyl 3-[(3-nitrophenyl)sulfonylamino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 BZTPNTVTJQTRRS-UHFFFAOYSA-N 0.000 description 1
JUWWGUMUVCLNGE-UHFFFAOYSA-N ethyl 3-[3-[[2-(diaminomethylideneamino)-1,3-thiazole-4-carbonyl]amino]propanoylamino]propanoate Chemical compound CCOC(=O)CCNC(=O)CCNC(=O)C1=CSC(NC(N)=N)=N1 JUWWGUMUVCLNGE-UHFFFAOYSA-N 0.000 description 1
VJOCSWOFCWONAL-UHFFFAOYSA-N ethyl 3-[3-[[2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carbonyl]amino]propanoylamino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CCNC(=O)C=1SC(NC(N)=N)=NC=1C VJOCSWOFCWONAL-UHFFFAOYSA-N 0.000 description 1
IZCVFLFCTYRCKU-UHFFFAOYSA-N ethyl 3-[4-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]phenyl]-3-(butylsulfonylamino)propanoate Chemical compound C1=CC(C(CC(=O)OCC)NS(=O)(=O)CCCC)=CC=C1NC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 IZCVFLFCTYRCKU-UHFFFAOYSA-N 0.000 description 1
RWEAHKOVFIYHMM-UHFFFAOYSA-N ethyl 3-[4-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]phenyl]-3-(propanoylamino)propanoate Chemical compound C1=CC(C(NC(=O)CC)CC(=O)OCC)=CC=C1NC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 RWEAHKOVFIYHMM-UHFFFAOYSA-N 0.000 description 1
RTHSBBQUGWDWFK-UHFFFAOYSA-N ethyl 3-[[2-(phenylmethoxycarbonylamino)acetyl]amino]-3-pyridin-3-ylpropanoate Chemical compound C=1C=CN=CC=1C(CC(=O)OCC)NC(=O)CNC(=O)OCC1=CC=CC=C1 RTHSBBQUGWDWFK-UHFFFAOYSA-N 0.000 description 1
QUPORJZPLDYZKG-UHFFFAOYSA-N ethyl 3-[[2-[[2-(diaminomethylideneamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CNC(=O)C1=CSC(NC(N)=N)=N1 QUPORJZPLDYZKG-UHFFFAOYSA-N 0.000 description 1
KOUGBMOUDNAJCR-UHFFFAOYSA-N ethyl 3-[[2-[[2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carbonyl]amino]acetyl]amino]propanoate Chemical compound CCOC(=O)CCNC(=O)CNC(=O)C=1SC(NC(N)=N)=NC=1C KOUGBMOUDNAJCR-UHFFFAOYSA-N 0.000 description 1
NNEPQQGEAOSJIT-UHFFFAOYSA-N ethyl 3-[[2-[[2-(diaminomethylideneamino)-5-(3-nitrophenyl)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CNC(=O)C=1N=C(NC(N)=N)SC=1C1=CC=CC([N+]([O-])=O)=C1 NNEPQQGEAOSJIT-UHFFFAOYSA-N 0.000 description 1
SPVHDETYCRKNHJ-UHFFFAOYSA-N ethyl 3-[[2-[[2-(diaminomethylideneamino)-5-phenyl-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CNC(=O)C=1N=C(NC(N)=N)SC=1C1=CC=CC=C1 SPVHDETYCRKNHJ-UHFFFAOYSA-N 0.000 description 1
LSLFCBDGSPYHLD-UHFFFAOYSA-N ethyl 3-[[3-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylmethoxybenzoyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)C(C=1)=CC(NC(=O)OC(C)(C)C)=CC=1OCC1=CC=CC=C1 LSLFCBDGSPYHLD-UHFFFAOYSA-N 0.000 description 1
ZHWSPOBJRJAOBV-UHFFFAOYSA-N ethyl 3-[[5-amino-2-(2-methoxyethoxy)benzoyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)C1=CC(N)=CC=C1OCCOC ZHWSPOBJRJAOBV-UHFFFAOYSA-N 0.000 description 1
PKEUKYSOLMJRJY-UHFFFAOYSA-N ethyl 3-amino-3-(4-nitrophenyl)propanoate Chemical compound CCOC(=O)CC(N)C1=CC=C([N+]([O-])=O)C=C1 PKEUKYSOLMJRJY-UHFFFAOYSA-N 0.000 description 1
GGANVLPLTUQZIF-UHFFFAOYSA-N ethyl 3-amino-3-pyridin-3-ylpropanoate;dihydrochloride Chemical compound Cl.Cl.CCOC(=O)CC(N)C1=CC=CN=C1 GGANVLPLTUQZIF-UHFFFAOYSA-N 0.000 description 1
MUDKQMLLCRJCEY-UHFFFAOYSA-N ethyl 3-cyclopentyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1CCCC1 MUDKQMLLCRJCEY-UHFFFAOYSA-N 0.000 description 1
OTKSIQOLKQEHMS-UHFFFAOYSA-N ethyl 3-phenyl-3-[3-(phenylmethoxycarbonylamino)propanoylamino]propanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CCNC(=O)OCC1=CC=CC=C1 OTKSIQOLKQEHMS-UHFFFAOYSA-N 0.000 description 1
GKPMCXGANOJOEV-UHFFFAOYSA-N ethyl 3-phenyl-3-[[2-(phenylmethoxycarbonylamino)acetyl]amino]propanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CNC(=O)OCC1=CC=CC=C1 GKPMCXGANOJOEV-UHFFFAOYSA-N 0.000 description 1
AZKRCSZYRXHRRY-UHFFFAOYSA-N ethyl 3-phenyl-3-[[2-[[2-(pyridin-2-ylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]propanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CNC(=O)C(N=1)=CSC=1NC1=CC=CC=N1 AZKRCSZYRXHRRY-UHFFFAOYSA-N 0.000 description 1
GGPHAOCGDDDDPS-UHFFFAOYSA-N ethyl 4-(2-amino-1,3-thiazol-4-yl)butanoate;hydrobromide Chemical compound Br.CCOC(=O)CCCC1=CSC(N)=N1 GGPHAOCGDDDDPS-UHFFFAOYSA-N 0.000 description 1
VZNBHLPEGALHOD-UHFFFAOYSA-N ethyl 4-[2-(benzylcarbamoylamino)-1,3-thiazol-4-yl]butanoate Chemical compound CCOC(=O)CCCC1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 VZNBHLPEGALHOD-UHFFFAOYSA-N 0.000 description 1
OHLRLMWUFVDREV-UHFFFAOYSA-N ethyl 4-chloro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CCl OHLRLMWUFVDREV-UHFFFAOYSA-N 0.000 description 1
QDWQJOXKKDTKDF-UHFFFAOYSA-N ethyl 4-methyl-2-(1,4,5,6-tetrahydropyrimidin-2-ylamino)-1,3-thiazole-5-carboxylate;hydrochloride Chemical compound Cl.CC1=C(C(=O)OCC)SC(N=C2NCCCN2)=N1 QDWQJOXKKDTKDF-UHFFFAOYSA-N 0.000 description 1
LSQDOEMPCMFDNM-UHFFFAOYSA-N ethyl 5-[3-[2-(diaminomethylideneamino)-4-methyl-1,3-thiazol-5-yl]anilino]-5-oxo-3-phenylpentanoate;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CC(=O)OCC)CC(=O)NC(C=1)=CC=CC=1C=1SC(NC(N)=N)=NC=1C LSQDOEMPCMFDNM-UHFFFAOYSA-N 0.000 description 1
SWFBUDHMLDCJAH-UHFFFAOYSA-N ethyl 5-oxo-6-[[2-(pyridin-2-ylmethylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]hexanoate Chemical compound CCOC(=O)CCCC(=O)CNC(=O)C1=CSC(NC(=O)NCC=2N=CC=CC=2)=N1 SWFBUDHMLDCJAH-UHFFFAOYSA-N 0.000 description 1
ULKLFVHWBJDORS-UHFFFAOYSA-N ethyl 6-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]-5-oxohexanoate Chemical compound CCOC(=O)CCCC(=O)CNC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 ULKLFVHWBJDORS-UHFFFAOYSA-N 0.000 description 1
UHLXSUPRMDBURL-UHFFFAOYSA-N ethyl 6-amino-3-benzyl-2-carbamoylhexanoate;hydrochloride Chemical compound Cl.CCOC(=O)C(C(N)=O)C(CCCN)CC1=CC=CC=C1 UHLXSUPRMDBURL-UHFFFAOYSA-N 0.000 description 1
MKKOGMDVCNTLLH-UHFFFAOYSA-N ethyl 6-amino-3-phenylhexanoate Chemical compound CCOC(=O)CC(CCCN)C1=CC=CC=C1 MKKOGMDVCNTLLH-UHFFFAOYSA-N 0.000 description 1
FIDGUPGOBSGZAT-UHFFFAOYSA-N ethyl 7-amino-3-phenylheptanoate Chemical compound CCOC(=O)CC(CCCCN)C1=CC=CC=C1 FIDGUPGOBSGZAT-UHFFFAOYSA-N 0.000 description 1
MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
229940117360 ethyl pyruvate Drugs 0.000 description 1
125000006125 ethylsulfonyl group Chemical group 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000011790 ferrous sulphate Substances 0.000 description 1
235000003891 ferrous sulphate Nutrition 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000008103 glucose Substances 0.000 description 1
150000002311 glutaric acids Chemical class 0.000 description 1
239000010439 graphite Substances 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004446 heteroarylalkyl group Chemical group 0.000 description 1
125000005842 heteroatom Chemical group 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
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 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
125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
102000018358 immunoglobulin Human genes 0.000 description 1
239000003547 immunosorbent Substances 0.000 description 1
238000011534 incubation Methods 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000008011 inorganic excipient Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000009545 invasion Effects 0.000 description 1
229960004903 invert sugar Drugs 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
229910000359 iron(II) sulfate Inorganic materials 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
238000002955 isolation Methods 0.000 description 1
125000005956 isoquinolyl group Chemical group 0.000 description 1
GDBQQVLCIARPGH-ULQDDVLXSA-N leupeptin Chemical compound CC(C)C[C@H](NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C=O)CCCN=C(N)N GDBQQVLCIARPGH-ULQDDVLXSA-N 0.000 description 1
108010052968 leupeptin Proteins 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000000873 masking effect Effects 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 description 1
IOVAQDNTCZXXEL-KRWDZBQOSA-N methyl (2s)-6-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate Chemical compound CC(C)(C)OC(=O)N[C@H](C(=O)OC)CCCCNC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 IOVAQDNTCZXXEL-KRWDZBQOSA-N 0.000 description 1
ZIKPYNINGZXCQW-UHFFFAOYSA-N methyl 2-(benzylcarbamoylamino)-5-methyl-1,3-thiazole-4-carboxylate Chemical compound S1C(C)=C(C(=O)OC)N=C1NC(=O)NCC1=CC=CC=C1 ZIKPYNINGZXCQW-UHFFFAOYSA-N 0.000 description 1
ZTBGQHIFGHSDIQ-UHFFFAOYSA-N methyl 2-(diaminomethylideneamino)-5-(3-nitrophenyl)-1,3-thiazole-4-carboxylate;hydrochloride Chemical compound Cl.N1=C(NC(N)=N)SC(C=2C=C(C=CC=2)[N+]([O-])=O)=C1C(=O)OC ZTBGQHIFGHSDIQ-UHFFFAOYSA-N 0.000 description 1
QGSWLUWVMUHGKD-UHFFFAOYSA-N methyl 2-(diaminomethylideneamino)-5-methyl-1,3-thiazole-4-carboxylate Chemical compound COC(=O)C=1N=C(NC(N)=N)SC=1C QGSWLUWVMUHGKD-UHFFFAOYSA-N 0.000 description 1
RQTLRHXKBMDFDN-UHFFFAOYSA-N methyl 2-(diaminomethylideneamino)-5-phenyl-1,3-thiazole-4-carboxylate Chemical compound N1=C(NC(N)=N)SC(C=2C=CC=CC=2)=C1C(=O)OC RQTLRHXKBMDFDN-UHFFFAOYSA-N 0.000 description 1
ZPFCEYUYBJVUED-UHFFFAOYSA-N methyl 2-amino-5-methyl-1,3-thiazole-4-carboxylate Chemical compound COC(=O)C=1N=C(N)SC=1C ZPFCEYUYBJVUED-UHFFFAOYSA-N 0.000 description 1
SIBQGZFJHNZQFH-SOFGYWHQSA-N methyl 3-[(e)-2-nitroprop-1-enyl]benzoate Chemical compound COC(=O)C1=CC=CC(\C=C(/C)[N+]([O-])=O)=C1 SIBQGZFJHNZQFH-SOFGYWHQSA-N 0.000 description 1
KEGHUPOMXKZHFC-UHFFFAOYSA-N methyl 3-[2-(diaminomethylideneamino)-4-methyl-1,3-thiazol-5-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C2=C(N=C(NC(N)=N)S2)C)=C1 KEGHUPOMXKZHFC-UHFFFAOYSA-N 0.000 description 1
RWGRTQSJMNLWAS-BQYQJAHWSA-N methyl 4-[(e)-2-nitroprop-1-enyl]benzoate Chemical compound COC(=O)C1=CC=C(\C=C(/C)[N+]([O-])=O)C=C1 RWGRTQSJMNLWAS-BQYQJAHWSA-N 0.000 description 1
DOLUSFMSYUAOIM-UHFFFAOYSA-N methyl 4-[2-(diaminomethylideneamino)-4-methyl-1,3-thiazol-5-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=C(C)N=C(NC(N)=N)S1 DOLUSFMSYUAOIM-UHFFFAOYSA-N 0.000 description 1
FEIOASZZURHTHB-UHFFFAOYSA-N methyl 4-formylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1 FEIOASZZURHTHB-UHFFFAOYSA-N 0.000 description 1
AYCRPDUURWNGHV-UHFFFAOYSA-N methyl 5-(3-aminophenyl)-2-(diaminomethylideneamino)-1,3-thiazole-4-carboxylate;hydrochloride Chemical compound Cl.N1=C(NC(N)=N)SC(C=2C=C(N)C=CC=2)=C1C(=O)OC AYCRPDUURWNGHV-UHFFFAOYSA-N 0.000 description 1
FTKXTSVTTHFNFH-UHFFFAOYSA-N methyl 5-[3-[2-(diaminomethylideneamino)-4-methyl-1,3-thiazol-5-yl]anilino]-5-oxo-4-(phenylmethoxycarbonylamino)pentanoate Chemical compound C=1C=CC(C2=C(N=C(NC(N)=N)S2)C)=CC=1NC(=O)C(CCC(=O)OC)NC(=O)OCC1=CC=CC=C1 FTKXTSVTTHFNFH-UHFFFAOYSA-N 0.000 description 1
TZJVWRXHKAXSEA-UHFFFAOYSA-N methyl 6-aminohexanoate Chemical compound COC(=O)CCCCCN TZJVWRXHKAXSEA-UHFFFAOYSA-N 0.000 description 1
125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
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BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
ZJXHVYSDMUKUCA-UHFFFAOYSA-N tert-butyl 3-aminopropanoate Chemical compound CC(C)(C)OC(=O)CCN ZJXHVYSDMUKUCA-UHFFFAOYSA-N 0.000 description 1
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QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
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150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1

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- 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
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- 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
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- 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
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- C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
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Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
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Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Physical Education & Sports Medicine (AREA)
Oncology (AREA)
Rheumatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Communicable Diseases (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Biophysics (AREA)
Dermatology (AREA)
Urology & Nephrology (AREA)
Heart & Thoracic Surgery (AREA)
Immunology (AREA)
Ophthalmology & Optometry (AREA)
Virology (AREA)
Cardiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
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HR98100006.0A 1998-01-02 1998-12-29 Thiazole derivatives HRP980645A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP98100006		1998-01-02

Publications (1)

Publication Number	Publication Date
HRP980645A2 true HRP980645A2 (en)	1999-10-31

Family

ID=8231229

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR98100006.0A HRP980645A2 (en)	1998-01-02	1998-12-29	Thiazole derivatives

Country Status (29)

Country	Link
US (3)	US6100282A (de)
JP (1)	JP3113237B2 (de)
KR (1)	KR100312901B1 (de)
CN (1)	CN1080720C (de)
AR (1)	AR014949A1 (de)
AT (1)	ATE233746T1 (de)
AU (1)	AU720618B2 (de)
BR (1)	BR9900006A (de)
CA (1)	CA2257328C (de)
CO (1)	CO4990934A1 (de)
DE (1)	DE69811844T2 (de)
DK (1)	DK0928790T3 (de)
ES (1)	ES2193471T3 (de)
HR (1)	HRP980645A2 (de)
HU (1)	HUP9803040A3 (de)
ID (1)	ID21936A (de)
IL (1)	IL127785A (de)
MA (1)	MA26591A1 (de)
NO (1)	NO312067B1 (de)
NZ (2)	NZ333590A (de)
PE (1)	PE20000061A1 (de)
PL (1)	PL330619A1 (de)
PT (1)	PT928790E (de)
RU (1)	RU2218337C2 (de)
SG (1)	SG74686A1 (de)
TR (1)	TR199802765A2 (de)
UY (1)	UY25334A1 (de)
YU (1)	YU61398A (de)
ZA (1)	ZA9811925B (de)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6919366B2 (en) *	1998-05-22	2005-07-19	Avanir Pharmaceuticals	Benzimidazole derivatives as modulators of IgE
US6911462B2 (en) *	1998-05-22	2005-06-28	Avanir Pharmaceuticals	Benzimidazole compounds for regulating IgE
IL142090A0 (en)	1998-10-22	2002-03-10	Hoffmann La Roche	Thiazole derivatives
GB9826174D0 (en) *	1998-11-30	1999-01-20	Celltech Therapeutics Ltd	Chemical compounds
WO2001004103A1 (en)	1999-07-13	2001-01-18	F. Hoffmann-La Roche Ag	Benzazepinones and quinazolines
US6759425B2 (en) *	1999-10-21	2004-07-06	Avanir Pharmaceuticals	Benzimidazole compounds for modulating IgE and inhibiting cellular proliferation
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1998
- 1998-12-22 US US09/218,567 patent/US6100282A/en not_active Expired - Fee Related
- 1998-12-24 ES ES98124670T patent/ES2193471T3/es not_active Expired - Lifetime
- 1998-12-24 AT AT98124670T patent/ATE233746T1/de not_active IP Right Cessation
- 1998-12-24 NZ NZ333590A patent/NZ333590A/xx unknown
- 1998-12-24 DK DK98124670T patent/DK0928790T3/da active
- 1998-12-24 PT PT98124670T patent/PT928790E/pt unknown
- 1998-12-24 DE DE69811844T patent/DE69811844T2/de not_active Expired - Fee Related
- 1998-12-24 NZ NZ333591A patent/NZ333591A/xx unknown
- 1998-12-28 NO NO19986159A patent/NO312067B1/no unknown
- 1998-12-29 AR ARP980106723A patent/AR014949A1/es not_active Application Discontinuation
- 1998-12-29 PE PE1998001293A patent/PE20000061A1/es not_active Application Discontinuation
- 1998-12-29 HR HR98100006.0A patent/HRP980645A2/hr not_active Application Discontinuation
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- 1998-12-30 SG SG1998005978A patent/SG74686A1/en unknown
- 1998-12-30 MA MA25411A patent/MA26591A1/fr unknown
- 1998-12-30 CO CO98077476A patent/CO4990934A1/es unknown
- 1998-12-30 PL PL98330619A patent/PL330619A1/xx not_active Application Discontinuation
- 1998-12-30 CA CA002257328A patent/CA2257328C/en not_active Expired - Fee Related
- 1998-12-30 AU AU96144/98A patent/AU720618B2/en not_active Ceased
- 1998-12-30 HU HU9803040A patent/HUP9803040A3/hu unknown
- 1998-12-30 YU YU61398A patent/YU61398A/sh unknown
- 1998-12-30 TR TR1998/02765A patent/TR199802765A2/xx unknown
- 1998-12-31 KR KR1019980063364A patent/KR100312901B1/ko not_active Expired - Fee Related
- 1998-12-31 CN CN98125982A patent/CN1080720C/zh not_active Expired - Fee Related
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1999
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2000
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2001
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Also Published As

Publication number	Publication date
CO4990934A1 (es)	2000-12-26
MA26591A1 (fr)	2004-12-20
DK0928790T3 (da)	2003-06-30
TR199802765A3 (tr)	1999-07-21
US6344562B1 (en)	2002-02-05
BR9900006A (pt)	2000-04-11
KR100312901B1 (ko)	2002-01-15
CA2257328A1 (en)	1999-07-02
HU9803040D0 (en)	1999-02-01
PL330619A1 (en)	1999-07-05
HUP9803040A3 (en)	2001-04-28
JP2000053664A (ja)	2000-02-22
ATE233746T1 (de)	2003-03-15
UY25334A1 (es)	2001-01-31
RU2218337C2 (ru)	2003-12-10
US6320054B1 (en)	2001-11-20
DE69811844D1 (de)	2003-04-10
IL127785A0 (en)	1999-10-28
US20020010316A1 (en)	2002-01-24
TR199802765A2 (xx)	1999-07-21
CA2257328C (en)	2006-05-09
YU61398A (sh)	2001-12-26
AR014949A1 (es)	2001-04-11
NZ333591A (en)	2000-05-26
NO986159L (no)	1999-07-05
HK1020953A1 (en)	2000-05-26
AU9614498A (en)	1999-07-22
IL127785A (en)	2004-09-27
NO986159D0 (no)	1998-12-28
ZA9811925B (en)	2000-06-29
CN1080720C (zh)	2002-03-13
CN1224718A (zh)	1999-08-04
HUP9803040A2 (hu)	2000-04-28
KR19990066925A (ko)	1999-08-16
SG74686A1 (en)	2000-08-22
PE20000061A1 (es)	2000-02-09
AU720618B2 (en)	2000-06-08
NO312067B1 (no)	2002-03-11
DE69811844T2 (de)	2003-12-04
ID21936A (id)	1999-08-12
ES2193471T3 (es)	2003-11-01
NZ333590A (en)	2000-05-26
US6100282A (en)	2000-08-08
JP3113237B2 (ja)	2000-11-27
PT928790E (pt)	2003-07-31

Legal Events

Date	Code	Title
1999-10-31	A1OB	Publication of a patent application
2000-04-26	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
2005-01-04	ODBC	Application rejected

Publication	Publication Date	Title
EP0928790B1 (de)	2003-03-05	Thiazole Derivate
CA2257328C (en)	2006-05-09	Thiazole derivatives
CZ207298A3 (cs)	1998-11-11	Fenylthiazolové deriváty, způsob výroby a farmaceutický prostředek
SK56798A3 (en)	1998-12-02	Protease inhibitors, pharmaceutical composition containing them and their use
DE69034202T2 (de)	2006-06-22	Zwischenprodukte zur Herstellung von non-peptiden retroviralproteasehemmenden Verbindungen
EP0928793B1 (de)	2002-05-15	Thiazol-Derivate
JP3530137B2 (ja)	2004-05-24	チアゾール誘導体
CA2257322C (en)	2003-11-04	Thiazole derivatives
CZ437098A3 (cs)	2000-01-12	Deriváty thiazolu
MXPA99000215A (en)	2000-06-01	Derivatives of tia
MXPA99000216A (en)	2000-06-01	Derivatives of tia
MXPA01004000A (en)	2001-11-21	Thiazole-derivatives