NO329175B1 - 5-fenyltiazolderivater, fremgangsmate for fremstilling derav, anvendelse av en slik forbindelse samt farmasoytisk sammensetning inneholdende forbindelsen - Google Patents
5-fenyltiazolderivater, fremgangsmate for fremstilling derav, anvendelse av en slik forbindelse samt farmasoytisk sammensetning inneholdende forbindelsen Download PDFInfo
- Publication number
- NO329175B1 NO329175B1 NO20044095A NO20044095A NO329175B1 NO 329175 B1 NO329175 B1 NO 329175B1 NO 20044095 A NO20044095 A NO 20044095A NO 20044095 A NO20044095 A NO 20044095A NO 329175 B1 NO329175 B1 NO 329175B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- optionally substituted
- hydroxy
- methyl
- phenyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 264
- 238000000034 method Methods 0.000 title claims description 105
- 238000002360 preparation method Methods 0.000 title claims description 28
- 230000008569 process Effects 0.000 title claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- ZLLOWHFKKIOINR-UHFFFAOYSA-N 5-phenyl-1,3-thiazole Chemical class S1C=NC=C1C1=CC=CC=C1 ZLLOWHFKKIOINR-UHFFFAOYSA-N 0.000 title 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 188
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 169
- 229910052757 nitrogen Inorganic materials 0.000 claims description 124
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 94
- 239000001301 oxygen Substances 0.000 claims description 94
- 229910052760 oxygen Inorganic materials 0.000 claims description 94
- 125000005842 heteroatom Chemical group 0.000 claims description 93
- 239000001257 hydrogen Substances 0.000 claims description 93
- 229910052739 hydrogen Inorganic materials 0.000 claims description 93
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 91
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 90
- -1 hydroxy, amino Chemical group 0.000 claims description 82
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 76
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 69
- 150000002825 nitriles Chemical group 0.000 claims description 68
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 67
- 239000005864 Sulphur Chemical group 0.000 claims description 62
- 229910052736 halogen Inorganic materials 0.000 claims description 61
- 150000002367 halogens Chemical group 0.000 claims description 61
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 56
- 238000006243 chemical reaction Methods 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 41
- 150000003839 salts Chemical group 0.000 claims description 35
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 31
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 29
- 150000002431 hydrogen Chemical class 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 24
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 17
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 229910021529 ammonia Inorganic materials 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 12
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 208000023504 respiratory system disease Diseases 0.000 claims description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 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 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 125000000565 sulfonamide group Chemical group 0.000 claims description 7
- 239000011593 sulfur Chemical group 0.000 claims description 7
- 229910052717 sulfur Chemical group 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 6
- 206010020751 Hypersensitivity Diseases 0.000 claims description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- ADUCIDRRGKFELT-UHFFFAOYSA-N 2-(dimethylamino)-n-(4-methyl-5-phenyl-1,3-thiazol-2-yl)acetamide Chemical compound S1C(NC(=O)CN(C)C)=NC(C)=C1C1=CC=CC=C1 ADUCIDRRGKFELT-UHFFFAOYSA-N 0.000 claims description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 4
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 3
- VBIGFUARFCCVEH-UHFFFAOYSA-N 4-(triazin-4-yl)morpholine Chemical compound C1COCCN1C1=CC=NN=N1 VBIGFUARFCCVEH-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
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 206010040070 Septic Shock Diseases 0.000 claims description 3
- 208000006011 Stroke Diseases 0.000 claims description 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 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 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000008177 pharmaceutical agent Substances 0.000 claims description 3
- 230000002062 proliferating effect Effects 0.000 claims description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 3
- 208000037803 restenosis Diseases 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 230000036303 septic shock Effects 0.000 claims description 3
- 150000003536 tetrazoles Chemical class 0.000 claims description 3
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 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
- 150000003852 triazoles Chemical class 0.000 claims description 3
- 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
- LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 claims description 2
- 208000025747 Rheumatic disease Diseases 0.000 claims description 2
- 230000007815 allergy Effects 0.000 claims description 2
- RXKVISPWRJYKMW-UHFFFAOYSA-N ethyl 3-[[5-[4-(dimethylsulfamoyl)phenyl]-4-methyl-1,3-thiazol-2-yl]carbamoylamino]propanoate Chemical compound S1C(NC(=O)NCCC(=O)OCC)=NC(C)=C1C1=CC=C(S(=O)(=O)N(C)C)C=C1 RXKVISPWRJYKMW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 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
- ZASMRPOKAYRYIC-UHFFFAOYSA-N n-[4-methyl-5-(4-sulfamoylphenyl)-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C)=C1C1=CC=C(S(N)(=O)=O)C=C1 ZASMRPOKAYRYIC-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
- NGCCPCSWRNFKDP-UHFFFAOYSA-N n-[4-methyl-5-[3-(4-methylpyrazol-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(N2N=CC(C)=C2)=C1 NGCCPCSWRNFKDP-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
- CCRGRSVYYUEDDI-UHFFFAOYSA-N n-[4-methyl-5-[4-methylsulfonyl-3-(2-propan-2-ylimidazol-1-yl)phenyl]-1,3-thiazol-2-yl]acetamide Chemical compound CC(C)C1=NC=CN1C1=CC(C2=C(N=C(NC(C)=O)S2)C)=CC=C1S(C)(=O)=O CCRGRSVYYUEDDI-UHFFFAOYSA-N 0.000 claims description 2
- GOHKFNRLRAIJSO-UHFFFAOYSA-N n-[5-[3-(2-hydroxyethylsulfamoyl)-4-methoxyphenyl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound C1=C(S(=O)(=O)NCCO)C(OC)=CC=C1C1=C(C)N=C(NC(C)=O)S1 GOHKFNRLRAIJSO-UHFFFAOYSA-N 0.000 claims description 2
- IWWYVZGQGNAVGJ-UHFFFAOYSA-N n-[5-[3-(2-hydroxyethylsulfamoyl)phenyl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C)=C1C1=CC=CC(S(=O)(=O)NCCO)=C1 IWWYVZGQGNAVGJ-UHFFFAOYSA-N 0.000 claims description 2
- XYHBQMRMZRNBLJ-UHFFFAOYSA-N n-[5-[3-(3-methoxypropylsulfamoyl)phenyl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound COCCCNS(=O)(=O)C1=CC=CC(C2=C(N=C(NC(C)=O)S2)C)=C1 XYHBQMRMZRNBLJ-UHFFFAOYSA-N 0.000 claims description 2
- GWQFCWCAMPUMAL-UHFFFAOYSA-N n-[5-[3-[2-(diethylamino)ethylamino]-4-methylsulfonylphenyl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound C1=C(S(C)(=O)=O)C(NCCN(CC)CC)=CC(C2=C(N=C(NC(C)=O)S2)C)=C1 GWQFCWCAMPUMAL-UHFFFAOYSA-N 0.000 claims description 2
- OOXQSFKKHRJLHH-UHFFFAOYSA-N n-[5-[4-(methanesulfonamido)phenyl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical group S1C(NC(=O)C)=NC(C)=C1C1=CC=C(NS(C)(=O)=O)C=C1 OOXQSFKKHRJLHH-UHFFFAOYSA-N 0.000 claims description 2
- DTYKXMLKBRSXBG-UHFFFAOYSA-N n-[5-[4-methoxy-3-(2-pyrrolidin-1-ylethylsulfamoyl)phenyl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound COC1=CC=C(C2=C(N=C(NC(C)=O)S2)C)C=C1S(=O)(=O)NCCN1CCCC1 DTYKXMLKBRSXBG-UHFFFAOYSA-N 0.000 claims description 2
- GBYQAIDAIROSTK-UHFFFAOYSA-N n-[5-[4-methoxy-3-(3-methoxypropylsulfamoyl)phenyl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound C1=C(OC)C(S(=O)(=O)NCCCOC)=CC(C2=C(N=C(NC(C)=O)S2)C)=C1 GBYQAIDAIROSTK-UHFFFAOYSA-N 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- JBMBQKGRQNOBOT-UHFFFAOYSA-N 2-[[5-[4-(dimethylsulfamoyl)phenyl]-4-methyl-1,3-thiazol-2-yl]carbamoylamino]acetic acid Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1C1=C(C)N=C(NC(=O)NCC(O)=O)S1 JBMBQKGRQNOBOT-UHFFFAOYSA-N 0.000 claims 1
- BIRRMKFFEKIFJS-UHFFFAOYSA-N n-[4-methyl-5-(4-methylsulfonylphenyl)-1,3-thiazol-2-yl]-2-(tetrazol-1-yl)acetamide Chemical compound S1C(C=2C=CC(=CC=2)S(C)(=O)=O)=C(C)N=C1NC(=O)CN1C=NN=N1 BIRRMKFFEKIFJS-UHFFFAOYSA-N 0.000 claims 1
- PSOJPFFVVSQMDS-UHFFFAOYSA-N n-[4-methyl-5-(4-methylsulfonylphenyl)-1,3-thiazol-2-yl]-2-pyridin-3-ylacetamide Chemical compound S1C(C=2C=CC(=CC=2)S(C)(=O)=O)=C(C)N=C1NC(=O)CC1=CC=CN=C1 PSOJPFFVVSQMDS-UHFFFAOYSA-N 0.000 claims 1
- LJCHOADLHCXSEA-UHFFFAOYSA-N n-[4-methyl-5-(4-methylsulfonylphenyl)-1,3-thiazol-2-yl]-2-pyridin-4-ylacetamide Chemical compound S1C(C=2C=CC(=CC=2)S(C)(=O)=O)=C(C)N=C1NC(=O)CC1=CC=NC=C1 LJCHOADLHCXSEA-UHFFFAOYSA-N 0.000 claims 1
- CDPSHQONYNLIBI-UHFFFAOYSA-N n-[4-methyl-5-(4-methylsulfonylphenyl)-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C)=C1C1=CC=C(S(C)(=O)=O)C=C1 CDPSHQONYNLIBI-UHFFFAOYSA-N 0.000 claims 1
- OBBWWEJDTXUNJB-UHFFFAOYSA-N n-[4-methyl-5-[3-(3-morpholin-4-ylpropylsulfamoyl)phenyl]-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C)=C1C1=CC=CC(S(=O)(=O)NCCCN2CCOCC2)=C1 OBBWWEJDTXUNJB-UHFFFAOYSA-N 0.000 claims 1
- KBHOLSMKJDPRKT-UHFFFAOYSA-N n-[4-methyl-5-[3-(4-methylpiperazin-1-yl)sulfonylphenyl]-1,3-thiazol-2-yl]acetamide Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=CC(C2=C(N=C(NC(C)=O)S2)C)=C1 KBHOLSMKJDPRKT-UHFFFAOYSA-N 0.000 claims 1
- BOMMHZMZVVNFDK-UHFFFAOYSA-N n-[4-methyl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C)=C1C1=CC=CC(C(F)(F)F)=C1 BOMMHZMZVVNFDK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- LLSZDFCMBAPLKH-UHFFFAOYSA-N n-[4-methyl-5-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C)=C1C1=CC=C(C(F)(F)F)C=C1 LLSZDFCMBAPLKH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
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- 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
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- 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
- C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
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- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
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- 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
- C07D417/10—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 carbon chain containing aromatic rings
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- 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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GB0229626A GB0229626D0 (en) | 2002-12-19 | 2002-12-19 | Organic compounds |
PCT/EP2003/002036 WO2003072557A1 (en) | 2002-02-28 | 2003-02-27 | 5-phenylthiazole derivatives and use as pi3 kinase inhibitors |
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NO20044095A NO329175B1 (no) | 2002-02-28 | 2004-09-27 | 5-fenyltiazolderivater, fremgangsmate for fremstilling derav, anvendelse av en slik forbindelse samt farmasoytisk sammensetning inneholdende forbindelsen |
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