PT1480962E - Derivados 5-feniltiazole e sua utilização como inibidores da pi3 cinase - Google Patents
Derivados 5-feniltiazole e sua utilização como inibidores da pi3 cinase Download PDFInfo
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- PT1480962E PT1480962E PT03709730T PT03709730T PT1480962E PT 1480962 E PT1480962 E PT 1480962E PT 03709730 T PT03709730 T PT 03709730T PT 03709730 T PT03709730 T PT 03709730T PT 1480962 E PT1480962 E PT 1480962E
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- Prior art keywords
- methyl
- phenyl
- thiazol
- alkyl
- optionally substituted
- Prior art date
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- ZLLOWHFKKIOINR-UHFFFAOYSA-N 5-phenyl-1,3-thiazole Chemical class S1C=NC=C1C1=CC=CC=C1 ZLLOWHFKKIOINR-UHFFFAOYSA-N 0.000 title 1
- 239000002935 phosphatidylinositol 3 kinase inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 266
- -1 hydroxy, amino Chemical group 0.000 claims description 230
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 190
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 158
- 229910052757 nitrogen Inorganic materials 0.000 claims description 126
- 238000000034 method Methods 0.000 claims description 102
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 95
- 229910052760 oxygen Inorganic materials 0.000 claims description 95
- 239000001301 oxygen Substances 0.000 claims description 95
- 125000005842 heteroatom Chemical group 0.000 claims description 93
- 229910052739 hydrogen Inorganic materials 0.000 claims description 92
- 239000001257 hydrogen Substances 0.000 claims description 88
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 83
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 82
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 69
- 229910052717 sulfur Chemical group 0.000 claims description 69
- 239000011593 sulfur Chemical group 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 65
- 229910052736 halogen Inorganic materials 0.000 claims description 56
- 150000002825 nitriles Chemical group 0.000 claims description 55
- 238000006243 chemical reaction Methods 0.000 claims description 50
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 47
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 46
- 150000002367 halogens Chemical class 0.000 claims description 39
- 239000000460 chlorine Substances 0.000 claims description 38
- 238000002360 preparation method Methods 0.000 claims description 36
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 33
- 150000003839 salts Chemical group 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 29
- 239000004202 carbamide Substances 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 27
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 150000002431 hydrogen Chemical group 0.000 claims description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 14
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 13
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 229910021529 ammonia Inorganic materials 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 10
- PPPPSVLHEUSSRU-UHFFFAOYSA-N 1-[2-(5-ethyl-1,3-oxazol-2-yl)ethyl]-3-[5-(3-fluoro-4-methylsulfonylphenyl)-4-methyl-1,3-thiazol-2-yl]urea Chemical compound O1C(CC)=CN=C1CCNC(=O)NC1=NC(C)=C(C=2C=C(F)C(=CC=2)S(C)(=O)=O)S1 PPPPSVLHEUSSRU-UHFFFAOYSA-N 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 8
- 208000023504 respiratory system disease Diseases 0.000 claims description 8
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 8
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 125000001246 bromo group Chemical group Br* 0.000 claims description 7
- 229940088679 drug related substance Drugs 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- SQWAXHGWLCYBIN-UHFFFAOYSA-N n-[5-(3-imidazol-1-yl-4-methylsulfonylphenyl)-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C)=C1C1=CC=C(S(C)(=O)=O)C(N2C=NC=C2)=C1 SQWAXHGWLCYBIN-UHFFFAOYSA-N 0.000 claims description 7
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 claims description 6
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 6
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 6
- LDOAOALGKACOAW-UHFFFAOYSA-N n-[5-(4-fluoro-3-methylsulfonylphenyl)-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C)=C1C1=CC=C(F)C(S(C)(=O)=O)=C1 LDOAOALGKACOAW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 5
- PPRAGLSLHZTNBC-UHFFFAOYSA-N [5-(3-fluoro-4-methylsulfonylphenyl)-4-methyl-1,3-thiazol-2-yl]urea Chemical compound N1=C(NC(N)=O)SC(C=2C=C(F)C(=CC=2)S(C)(=O)=O)=C1C PPRAGLSLHZTNBC-UHFFFAOYSA-N 0.000 claims description 5
- 239000000739 antihistaminic agent Substances 0.000 claims description 5
- 229940124630 bronchodilator Drugs 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- WPZBZYXQEWNADH-UHFFFAOYSA-N n-[5-(4-amino-3-chlorophenyl)-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C)=C1C1=CC=C(N)C(Cl)=C1 WPZBZYXQEWNADH-UHFFFAOYSA-N 0.000 claims description 5
- BLAWDMXWPWLUSS-UHFFFAOYSA-N n-[5-(4-fluoro-3-methoxyphenyl)-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound C1=C(F)C(OC)=CC(C2=C(N=C(NC(C)=O)S2)C)=C1 BLAWDMXWPWLUSS-UHFFFAOYSA-N 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- NPWIUHZOQLKPPT-UHFFFAOYSA-N 1-ethyl-3-[5-(4-methoxy-3-sulfamoylphenyl)-4-methyl-1,3-thiazol-2-yl]urea Chemical compound S1C(NC(=O)NCC)=NC(C)=C1C1=CC=C(OC)C(S(N)(=O)=O)=C1 NPWIUHZOQLKPPT-UHFFFAOYSA-N 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- ZANZUBVWAYFCMR-UHFFFAOYSA-N ethyl 2-[[4-methyl-5-(4-methylsulfonylphenyl)-1,3-thiazol-2-yl]carbamoylamino]acetate Chemical compound S1C(NC(=O)NCC(=O)OCC)=NC(C)=C1C1=CC=C(S(C)(=O)=O)C=C1 ZANZUBVWAYFCMR-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 230000002140 halogenating effect Effects 0.000 claims description 4
- KONGCPZIQBNFFO-UHFFFAOYSA-N n-[5-(3,5-dichloro-4-sulfamoylphenyl)-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C)=C1C1=CC(Cl)=C(S(N)(=O)=O)C(Cl)=C1 KONGCPZIQBNFFO-UHFFFAOYSA-N 0.000 claims description 4
- OHIBLPNNUVWNGN-UHFFFAOYSA-N n-[5-(4-methoxy-3-methylsulfonylphenyl)-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound C1=C(S(C)(=O)=O)C(OC)=CC=C1C1=C(C)N=C(NC(C)=O)S1 OHIBLPNNUVWNGN-UHFFFAOYSA-N 0.000 claims description 4
- KKWCKZYYHPBBGW-UHFFFAOYSA-N n-[5-[4-(dimethylsulfamoyl)phenyl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1C1=C(C)N=C(NC(C)=O)S1 KKWCKZYYHPBBGW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims description 3
- PWZVZMGWOACAPW-UHFFFAOYSA-N 1-ethyl-3-[5-[3-(2-hydroxyethylsulfamoyl)-4-methoxyphenyl]-4-methyl-1,3-thiazol-2-yl]urea Chemical compound S1C(NC(=O)NCC)=NC(C)=C1C1=CC=C(OC)C(S(=O)(=O)NCCO)=C1 PWZVZMGWOACAPW-UHFFFAOYSA-N 0.000 claims description 3
- BQVLJQOSFIPPLC-UHFFFAOYSA-N 3-[[5-[4-(dimethylsulfamoyl)phenyl]-4-methyl-1,3-thiazol-2-yl]carbamoylamino]propanoic acid Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1C1=C(C)N=C(NC(=O)NCCC(O)=O)S1 BQVLJQOSFIPPLC-UHFFFAOYSA-N 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
- 208000011231 Crohn disease Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 206010040070 Septic Shock Diseases 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- IDCWVFZQXFUTTD-UHFFFAOYSA-N n-[4-methyl-5-[4-(methylsulfamoyl)phenyl]-1,3-thiazol-2-yl]acetamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1C1=C(C)N=C(NC(C)=O)S1 IDCWVFZQXFUTTD-UHFFFAOYSA-N 0.000 claims description 3
- BJTKETLLPYADQV-UHFFFAOYSA-N n-[5-[3-[2-(dimethylamino)ethylsulfamoyl]-4-methoxyphenyl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound C1=C(S(=O)(=O)NCCN(C)C)C(OC)=CC=C1C1=C(C)N=C(NC(C)=O)S1 BJTKETLLPYADQV-UHFFFAOYSA-N 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 229940080818 propionamide Drugs 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 230000036303 septic shock Effects 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- 238000002054 transplantation Methods 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- UGIYMTKVJXUVNJ-UHFFFAOYSA-N 1-(2-cyanoethyl)-3-[5-(3-fluoro-4-methylsulfonylphenyl)-4-methyl-1,3-thiazol-2-yl]urea Chemical compound N1=C(NC(=O)NCCC#N)SC(C=2C=C(F)C(=CC=2)S(C)(=O)=O)=C1C UGIYMTKVJXUVNJ-UHFFFAOYSA-N 0.000 claims description 2
- MLVZDFPXEVDJHT-UHFFFAOYSA-N 1-(2-cyanoethyl)-3-[5-(3-imidazol-1-yl-4-methylsulfonylphenyl)-4-methyl-1,3-thiazol-2-yl]urea Chemical compound N1=C(NC(=O)NCCC#N)SC(C=2C=C(C(=CC=2)S(C)(=O)=O)N2C=NC=C2)=C1C MLVZDFPXEVDJHT-UHFFFAOYSA-N 0.000 claims description 2
- PDTSKFRVTLPRLM-UHFFFAOYSA-N 1-(4-hydroxybutyl)-3-[5-(3-imidazol-1-yl-4-methylsulfonylphenyl)-4-methyl-1,3-thiazol-2-yl]urea Chemical compound N1=C(NC(=O)NCCCCO)SC(C=2C=C(C(=CC=2)S(C)(=O)=O)N2C=NC=C2)=C1C PDTSKFRVTLPRLM-UHFFFAOYSA-N 0.000 claims description 2
- CBIMMMJEDROKSF-UHFFFAOYSA-N 1-[5-(3-fluoro-4-methylsulfonylphenyl)-4-methyl-1,3-thiazol-2-yl]-3-[2-(5-methyl-1,3-oxazol-2-yl)ethyl]urea Chemical compound O1C(C)=CN=C1CCNC(=O)NC1=NC(C)=C(C=2C=C(F)C(=CC=2)S(C)(=O)=O)S1 CBIMMMJEDROKSF-UHFFFAOYSA-N 0.000 claims description 2
- XXPMOUWNALRVOS-UHFFFAOYSA-N 1-[5-(4-chloro-3-methylsulfonylphenyl)-4-methyl-1,3-thiazol-2-yl]-3-propan-2-ylurea Chemical compound S1C(NC(=O)NC(C)C)=NC(C)=C1C1=CC=C(Cl)C(S(C)(=O)=O)=C1 XXPMOUWNALRVOS-UHFFFAOYSA-N 0.000 claims description 2
- IVOCCUBEMNZBRL-UHFFFAOYSA-N 1-[5-[3-[2-(dimethylamino)ethyl-methylamino]-4-methylsulfonylphenyl]-4-methyl-1,3-thiazol-2-yl]-3-ethylurea Chemical compound S1C(NC(=O)NCC)=NC(C)=C1C1=CC=C(S(C)(=O)=O)C(N(C)CCN(C)C)=C1 IVOCCUBEMNZBRL-UHFFFAOYSA-N 0.000 claims description 2
- KLOPRCJFTAMUMQ-UHFFFAOYSA-N 1-butyl-3-[5-(4-chloro-3-methylsulfonylphenyl)-4-methyl-1,3-thiazol-2-yl]urea Chemical compound S1C(NC(=O)NCCCC)=NC(C)=C1C1=CC=C(Cl)C(S(C)(=O)=O)=C1 KLOPRCJFTAMUMQ-UHFFFAOYSA-N 0.000 claims description 2
- ISCVJALAVAXARV-UHFFFAOYSA-N 2-(diethylamino)-n-(4-methyl-5-phenyl-1,3-thiazol-2-yl)acetamide Chemical compound S1C(NC(=O)CN(CC)CC)=NC(C)=C1C1=CC=CC=C1 ISCVJALAVAXARV-UHFFFAOYSA-N 0.000 claims description 2
- CWTIGYSNISDUHL-UHFFFAOYSA-N 2-[[4-methyl-5-(4-methylsulfonylphenyl)-1,3-thiazol-2-yl]carbamoylamino]acetic acid Chemical compound N1=C(NC(=O)NCC(O)=O)SC(C=2C=CC(=CC=2)S(C)(=O)=O)=C1C CWTIGYSNISDUHL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
- CUFNRUNDKUWONG-UHFFFAOYSA-N 4-(2-acetamido-4-methyl-1,3-thiazol-5-yl)-2,6-dibromobenzenesulfonic acid Chemical compound S1C(NC(=O)C)=NC(C)=C1C1=CC(Br)=C(S(O)(=O)=O)C(Br)=C1 CUFNRUNDKUWONG-UHFFFAOYSA-N 0.000 claims description 2
- 101100134927 Gallus gallus COR8 gene Proteins 0.000 claims description 2
- 101100533877 Hypocrea jecorina (strain QM6a) sor8 gene Chemical group 0.000 claims description 2
- 230000001387 anti-histamine Effects 0.000 claims description 2
- IHRXPONHDXFADW-UHFFFAOYSA-N ethyl 4-[[4-methyl-5-[4-methylsulfonyl-3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]carbamoylamino]butanoate Chemical compound S1C(NC(=O)NCCCC(=O)OCC)=NC(C)=C1C1=CC=C(S(C)(=O)=O)C(C(F)(F)F)=C1 IHRXPONHDXFADW-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- DNBSFXNLTUCKCZ-UHFFFAOYSA-N n-(4-methyl-5-phenyl-1,3-thiazol-2-yl)-2-piperidin-1-ylacetamide Chemical compound S1C(C=2C=CC=CC=2)=C(C)N=C1NC(=O)CN1CCCCC1 DNBSFXNLTUCKCZ-UHFFFAOYSA-N 0.000 claims description 2
- AAFCPZDYHNNDLG-UHFFFAOYSA-N n-[4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C=2C=C(C=CC=2)C(F)(F)F)=C1 AAFCPZDYHNNDLG-UHFFFAOYSA-N 0.000 claims description 2
- PFWZOMDQGFWIKD-UHFFFAOYSA-N n-[4-methyl-5-(3-methylsulfonylphenyl)-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C)=C1C1=CC=CC(S(C)(=O)=O)=C1 PFWZOMDQGFWIKD-UHFFFAOYSA-N 0.000 claims description 2
- MDSWJBKGNABXGN-UHFFFAOYSA-N n-[4-methyl-5-[3-(2-methylimidazol-1-yl)-4-methylsulfonylphenyl]-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C)=C1C1=CC=C(S(C)(=O)=O)C(N2C(=NC=C2)C)=C1 MDSWJBKGNABXGN-UHFFFAOYSA-N 0.000 claims description 2
- FWUILGRVGSPAOL-UHFFFAOYSA-N n-[4-methyl-5-[3-(4-methylimidazol-1-yl)-4-methylsulfonylphenyl]-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C)=C1C1=CC=C(S(C)(=O)=O)C(N2C=C(C)N=C2)=C1 FWUILGRVGSPAOL-UHFFFAOYSA-N 0.000 claims description 2
- HGIYHJGEDZWRAI-UHFFFAOYSA-N n-[4-methyl-5-[4-methylsulfonyl-3-(1,2,4-triazol-1-yl)phenyl]-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C)=C1C1=CC=C(S(C)(=O)=O)C(N2N=CN=C2)=C1 HGIYHJGEDZWRAI-UHFFFAOYSA-N 0.000 claims description 2
- AVTAWKOBIFGNGY-UHFFFAOYSA-N n-[4-methyl-5-[4-methylsulfonyl-3-(2-propylimidazol-1-yl)phenyl]-1,3-thiazol-2-yl]acetamide Chemical compound CCCC1=NC=CN1C1=CC(C2=C(N=C(NC(C)=O)S2)C)=CC=C1S(C)(=O)=O AVTAWKOBIFGNGY-UHFFFAOYSA-N 0.000 claims description 2
- BIMGXQPYQGOJMS-UHFFFAOYSA-N n-[5-(3,4-dimethoxyphenyl)-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=C(C)N=C(NC(C)=O)S1 BIMGXQPYQGOJMS-UHFFFAOYSA-N 0.000 claims description 2
- KZOOIFCUGFZMMO-UHFFFAOYSA-N n-[5-(3,5-dichlorophenyl)-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C)=C1C1=CC(Cl)=CC(Cl)=C1 KZOOIFCUGFZMMO-UHFFFAOYSA-N 0.000 claims description 2
- WEIVNCCWFUUTHO-UHFFFAOYSA-N n-[5-(3,5-difluoro-4-methylsulfonylphenyl)-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C)=C1C1=CC(F)=C(S(C)(=O)=O)C(F)=C1 WEIVNCCWFUUTHO-UHFFFAOYSA-N 0.000 claims description 2
- CPDASYVBDNZTSW-UHFFFAOYSA-N n-[5-(3-bromo-4-methylsulfonylphenyl)-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C)=C1C1=CC=C(S(C)(=O)=O)C(Br)=C1 CPDASYVBDNZTSW-UHFFFAOYSA-N 0.000 claims description 2
- JKTIFEDMWIOIIM-UHFFFAOYSA-N n-[5-(3-chloro-4-methylsulfonylphenyl)-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C)=C1C1=CC=C(S(C)(=O)=O)C(Cl)=C1 JKTIFEDMWIOIIM-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0204765A GB0204765D0 (en) | 2002-02-28 | 2002-02-28 | Organic compounds |
| GB0229626A GB0229626D0 (en) | 2002-12-19 | 2002-12-19 | Organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT1480962E true PT1480962E (pt) | 2011-12-15 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT03709730T PT1480962E (pt) | 2002-02-28 | 2003-02-27 | Derivados 5-feniltiazole e sua utilização como inibidores da pi3 cinase |
| PT101745289T PT2311818E (pt) | 2002-02-28 | 2003-02-27 | Combinação de um composto de 5-feniltiazole como inibidor de quinase pi3 com um fármaco anti-inflamatório, broncodilatador ou anti-histamínico |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT101745289T PT2311818E (pt) | 2002-02-28 | 2003-02-27 | Combinação de um composto de 5-feniltiazole como inibidor de quinase pi3 com um fármaco anti-inflamatório, broncodilatador ou anti-histamínico |
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