OA12963A - Novel chemical compounds. - Google Patents

Novel chemical compounds. Download PDF

Info

Publication number: OA12963A
Authority: OA; OAPI
Prior art keywords: ylmethylene; thiazolidin; phenylimino; dihydro; thiazol
Prior art date: 2002-11-22

Application number

OA1200500154A

Other languages

English (en)

Inventor

Masaichi Hasegawa

Hideyuki Sato

Jun TANG

Original Assignee

Smithkline Beecham Corp

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.)

2002-11-22

Filing date

2003-11-18

Publication date

2006-10-13

2003-11-18 Application filed by Smithkline Beecham Corp filed Critical Smithkline Beecham Corp

2006-10-13 Publication of OA12963A publication Critical patent/OA12963A/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 99
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 20
201000010099 disease Diseases 0.000 claims abstract description 17
230000000694 effects Effects 0.000 claims abstract description 12
230000002401 inhibitory effect Effects 0.000 claims abstract description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 48
229910052736 halogen Inorganic materials 0.000 claims description 33
150000002367 halogens Chemical group 0.000 claims description 33
239000001257 hydrogen Substances 0.000 claims description 33
229910052739 hydrogen Inorganic materials 0.000 claims description 33
150000002431 hydrogen Chemical group 0.000 claims description 32
-1 Benzoicacid N'-[5-(2,3-dihydro-benzofuran-5-ylmethylene)-4-oxo-4,5-dihydro-thiazol-2-yl]-hydrazide 5-Benzo[1,2,5]thiadiazol-5-ylmethylene-2-(2,3,4-trifluoro-phenylamino)-thiazol-4-one Chemical compound 0.000 claims description 26
125000000217 alkyl group Chemical group 0.000 claims description 22
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
239000008194 pharmaceutical composition Substances 0.000 claims description 18
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
229910006074 SO2NH2 Inorganic materials 0.000 claims description 12
125000001841 imino group Chemical group [H]N=* 0.000 claims description 11
239000003085 diluting agent Substances 0.000 claims description 10
239000000546 pharmaceutical excipient Substances 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
206010065553 Bone marrow failure Diseases 0.000 claims description 8
241000124008 Mammalia Species 0.000 claims description 8
201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 8
206010033661 Pancytopenia Diseases 0.000 claims description 8
208000024389 cytopenia Diseases 0.000 claims description 8
239000003937 drug carrier Substances 0.000 claims description 8
230000000925 erythroid effect Effects 0.000 claims description 8
HKXHMLKRTGODRT-UHFFFAOYSA-N 2-(2-chloroanilino)-5-[(2-oxochromen-6-yl)methylidene]-1,3-thiazol-4-one Chemical compound ClC1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(OC(=O)C=C2)C2=C1 HKXHMLKRTGODRT-UHFFFAOYSA-N 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 6
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
OVHGJDOCDAMKTG-UHFFFAOYSA-N 2-(2-methylsulfanylanilino)-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound CSC1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(N=CC=C2)C2=C1 OVHGJDOCDAMKTG-UHFFFAOYSA-N 0.000 claims description 5
YNJOEMDKWQEARA-UHFFFAOYSA-N 2-[2,4-dichloro-5-[[4-oxo-5-(quinolin-6-ylmethylidene)-1,3-thiazol-2-yl]amino]phenoxy]acetic acid Chemical compound C1=C(Cl)C(OCC(=O)O)=CC(N=C2SC(C(=O)N2)=CC=2C=C3C=CC=NC3=CC=2)=C1Cl YNJOEMDKWQEARA-UHFFFAOYSA-N 0.000 claims description 5
210000000777 hematopoietic system Anatomy 0.000 claims description 5
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 claims description 3
SJCVUBKFMNLKNH-UHFFFAOYSA-N 1-[[5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-4-oxo-1,3-thiazol-2-yl]amino]-3-phenylurea Chemical compound N=1C(=O)C(=CC=2C=C3CCOC3=CC=2)SC=1NNC(=O)NC1=CC=CC=C1 SJCVUBKFMNLKNH-UHFFFAOYSA-N 0.000 claims description 3
SRDGYKQKWIQUGB-UHFFFAOYSA-N 2-(2,6-dichloroanilino)-5-[(2-methoxypyridin-3-yl)methylidene]-1,3-thiazol-4-one Chemical compound COC1=NC=CC=C1C=C1C(=O)N=C(NC=2C(=CC=CC=2Cl)Cl)S1 SRDGYKQKWIQUGB-UHFFFAOYSA-N 0.000 claims description 3
GDRMNTFZVIQOBU-UHFFFAOYSA-N 2-(2-bromoanilino)-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound BrC1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(N=CC=C2)C2=C1 GDRMNTFZVIQOBU-UHFFFAOYSA-N 0.000 claims description 3
PIOZRFOSBSXDQS-UHFFFAOYSA-N 2-(2-bromoanilino)-5-[(3,4-diaminophenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=C(N)C(N)=CC=C1C=C1C(=O)N=C(NC=2C(=CC=CC=2)Br)S1 PIOZRFOSBSXDQS-UHFFFAOYSA-N 0.000 claims description 3
SXQCFGHYESQTLV-UHFFFAOYSA-N 2-(2-bromoanilino)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=C(O)C(OC)=CC(C=C2C(N=C(NC=3C(=CC=CC=3)Br)S2)=O)=C1 SXQCFGHYESQTLV-UHFFFAOYSA-N 0.000 claims description 3
TVCRMIHVSUPCBA-UHFFFAOYSA-N 2-(2-bromoanilino)-5-[(5-pyridin-2-ylthiophen-2-yl)methylidene]-1,3-thiazol-4-one Chemical compound BrC1=CC=CC=C1NC(S1)=NC(=O)C1=CC1=CC=C(C=2N=CC=CC=2)S1 TVCRMIHVSUPCBA-UHFFFAOYSA-N 0.000 claims description 3
GWOKZFNBGFQXEJ-UHFFFAOYSA-N 2-(2-chloro-5-fluoroanilino)-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound FC1=CC=C(Cl)C(N=C2SC(C(=O)N2)=CC=2C=C3C=CC=NC3=CC=2)=C1 GWOKZFNBGFQXEJ-UHFFFAOYSA-N 0.000 claims description 3
YJSBQIJOLWMMHY-UHFFFAOYSA-N 2-(2-chloro-5-fluoroanilino)-5-[(3-fluoro-4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=C(F)C(O)=CC=C1C=C(S1)C(=O)NC1=NC1=CC(F)=CC=C1Cl YJSBQIJOLWMMHY-UHFFFAOYSA-N 0.000 claims description 3
DFCWVGVVXKQZLU-UHFFFAOYSA-N 2-(2-chloro-5-nitroanilino)-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(NC=2SC(C(=O)N=2)=CC=2C=C3C=CC=NC3=CC=2)=C1 DFCWVGVVXKQZLU-UHFFFAOYSA-N 0.000 claims description 3
KCNYITTZCXIVRV-UHFFFAOYSA-N 2-(2-chloroanilino)-5-[(3-fluoro-4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=C(F)C(O)=CC=C1C=C(S1)C(=O)NC1=NC1=CC=CC=C1Cl KCNYITTZCXIVRV-UHFFFAOYSA-N 0.000 claims description 3
HROXESYKDDDRDE-UHFFFAOYSA-N 2-(2-chloroanilino)-5-[(4-methoxyphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=CC(OC)=CC=C1C=C1C(=O)N=C(NC=2C(=CC=CC=2)Cl)S1 HROXESYKDDDRDE-UHFFFAOYSA-N 0.000 claims description 3
NCUXQKKLXYTAQV-UHFFFAOYSA-N 2-(5-amino-2-chloroanilino)-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound NC1=CC=C(Cl)C(NC=2SC(C(=O)N=2)=CC=2C=C3C=CC=NC3=CC=2)=C1 NCUXQKKLXYTAQV-UHFFFAOYSA-N 0.000 claims description 3
YMMCZMKMBHMOCP-UHFFFAOYSA-N 2-(cyclohexylamino)-5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-1,3-thiazol-4-one Chemical compound S1C(=CC=2C=C3CCOC3=CC=2)C(=O)NC1=NC1CCCCC1 YMMCZMKMBHMOCP-UHFFFAOYSA-N 0.000 claims description 3
FAIDCLADJUCIEJ-UHFFFAOYSA-N 2-(naphthalen-1-ylamino)-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound C1=CC=C2C(N=C3NC(C(S3)=CC=3C=C4C=CC=NC4=CC=3)=O)=CC=CC2=C1 FAIDCLADJUCIEJ-UHFFFAOYSA-N 0.000 claims description 3
LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 claims description 3
BGIOOZLTFRLJFX-UHFFFAOYSA-N 5-(1,3-benzothiazol-6-ylmethylidene)-2-(2,6-dichloroanilino)-1,3-thiazol-4-one Chemical compound ClC1=CC=CC(Cl)=C1N=C(NC1=O)SC1=CC1=CC=C(N=CS2)C2=C1 BGIOOZLTFRLJFX-UHFFFAOYSA-N 0.000 claims description 3
LSEIJMMQMSIIHW-UHFFFAOYSA-N 5-(1,3-benzothiazol-6-ylmethylidene)-2-(2-chloroanilino)-1,3-thiazol-4-one Chemical compound ClC1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(N=CS2)C2=C1 LSEIJMMQMSIIHW-UHFFFAOYSA-N 0.000 claims description 3
HMPGPXKJSANJSV-UHFFFAOYSA-N 5-(2,1,3-benzothiadiazol-5-ylmethylidene)-2-(2,6-dichloroanilino)-1,3-thiazol-4-one Chemical compound ClC1=CC=CC(Cl)=C1NC(S1)=NC(=O)C1=CC1=CC2=NSN=C2C=C1 HMPGPXKJSANJSV-UHFFFAOYSA-N 0.000 claims description 3
QKIMYAFLXQGKGC-UHFFFAOYSA-N 5-(2,1,3-benzoxadiazol-5-ylmethylidene)-2-(2-bromoanilino)-1,3-thiazol-4-one Chemical compound BrC1=CC=CC=C1NC(S1)=NC(=O)C1=CC1=CC2=NON=C2C=C1 QKIMYAFLXQGKGC-UHFFFAOYSA-N 0.000 claims description 3
RGCOBTHQLMYNSE-UHFFFAOYSA-N 5-(2,1,3-benzoxadiazol-5-ylmethylidene)-2-(2-nitroanilino)-1,3-thiazol-4-one Chemical compound [O-][N+](=O)C1=CC=CC=C1NC(S1)=NC(=O)C1=CC1=CC2=NON=C2C=C1 RGCOBTHQLMYNSE-UHFFFAOYSA-N 0.000 claims description 3
YCAQTHIDBNIVRV-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-(2-fluoroanilino)-1,3-thiazol-4-one Chemical compound FC1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(OCC2)C2=C1 YCAQTHIDBNIVRV-UHFFFAOYSA-N 0.000 claims description 3
AQBZPOMLIXGKMH-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-(piperidin-1-ylamino)-1,3-thiazol-4-one Chemical compound S1C(=CC=2C=C3CCOC3=CC=2)C(=O)N=C1NN1CCCCC1 AQBZPOMLIXGKMH-UHFFFAOYSA-N 0.000 claims description 3
MKNCBJKHPMAYDN-UHFFFAOYSA-N 5-(quinolin-6-ylmethylidene)-2-(2,3,4-trifluoroanilino)-1,3-thiazol-4-one Chemical compound FC1=C(F)C(F)=CC=C1NC(S1)=NC(=O)C1=CC1=CC=C(N=CC=C2)C2=C1 MKNCBJKHPMAYDN-UHFFFAOYSA-N 0.000 claims description 3
XWGICUGRIRKTAR-UHFFFAOYSA-N 5-(quinolin-6-ylmethylidene)-2-[2-(trifluoromethyl)anilino]-1,3-thiazol-4-one Chemical compound FC(F)(F)C1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(N=CC=C2)C2=C1 XWGICUGRIRKTAR-UHFFFAOYSA-N 0.000 claims description 3
239000000969 carrier Substances 0.000 claims description 3
CQMJIMNBQHFSGT-UHFFFAOYSA-N n'-[4-chloro-3-[[4-oxo-5-(quinolin-6-ylmethylidene)-1,3-thiazol-2-yl]amino]phenyl]ethanimidamide;hydrochloride Chemical compound Cl.CC(=N)NC1=CC=C(Cl)C(NC=2SC(C(=O)N=2)=CC=2C=C3C=CC=NC3=CC=2)=C1 CQMJIMNBQHFSGT-UHFFFAOYSA-N 0.000 claims description 3
YMYXOXZEFSEVLK-UHFFFAOYSA-N n'-[4-oxo-5-(quinolin-6-ylmethylidene)-1,3-thiazol-2-yl]benzohydrazide Chemical compound N=1C(=O)C(=CC=2C=C3C=CC=NC3=CC=2)SC=1NNC(=O)C1=CC=CC=C1 YMYXOXZEFSEVLK-UHFFFAOYSA-N 0.000 claims description 3
SHXHWOPEFBMMKJ-ZSOIEALJSA-N (5z)-2-(2-chloroanilino)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=C([N+]([O-])=O)C(O)=CC=C1\C=C/1C(=O)N=C(NC=2C(=CC=CC=2)Cl)S\1 SHXHWOPEFBMMKJ-ZSOIEALJSA-N 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
IUKRVEKIIMLFHP-UHFFFAOYSA-N 2-(2,3-dimethylanilino)-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound CC1=CC=CC(N=C2SC(C(=O)N2)=CC=2C=C3C=CC=NC3=CC=2)=C1C IUKRVEKIIMLFHP-UHFFFAOYSA-N 0.000 claims description 2
WTXCTIAIASNBBY-UHFFFAOYSA-N 2-(2,6-dichloroanilino)-5-[(2-oxochromen-6-yl)methylidene]-1,3-thiazol-4-one Chemical compound ClC1=CC=CC(Cl)=C1NC(S1)=NC(=O)C1=CC1=CC=C(OC(=O)C=C2)C2=C1 WTXCTIAIASNBBY-UHFFFAOYSA-N 0.000 claims description 2
VIXVBMOJVIWSHX-UHFFFAOYSA-N 2-(2,6-dichloroanilino)-5-[(3-fluoro-4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=C(F)C(O)=CC=C1C=C(S1)C(=O)NC1=NC1=C(Cl)C=CC=C1Cl VIXVBMOJVIWSHX-UHFFFAOYSA-N 0.000 claims description 2
WBDCUAJMKUWGCL-UHFFFAOYSA-N 2-(2,6-dichloroanilino)-5-[[4-(1,2,4-triazol-1-yl)phenyl]methylidene]-1,3-thiazol-4-one Chemical compound ClC1=CC=CC(Cl)=C1NC(S1)=NC(=O)C1=CC1=CC=C(N2N=CN=C2)C=C1 WBDCUAJMKUWGCL-UHFFFAOYSA-N 0.000 claims description 2
ZMKDBVLGOUMDNV-UHFFFAOYSA-N 2-(2-bromo-6-fluoroanilino)-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound FC1=CC=CC(Br)=C1NC(S1)=NC(=O)C1=CC1=CC=C(N=CC=C2)C2=C1 ZMKDBVLGOUMDNV-UHFFFAOYSA-N 0.000 claims description 2
SBMUSODKGJAUBZ-UHFFFAOYSA-N 2-(2-chloroanilino)-5-(quinoxalin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound ClC1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(N=CC=N2)C2=C1 SBMUSODKGJAUBZ-UHFFFAOYSA-N 0.000 claims description 2
QVGNNTDUNPSZJY-UHFFFAOYSA-N 2-(2-chloroanilino)-5-[(1-methyl-6-oxopyridin-3-yl)methylidene]-1,3-thiazol-4-one Chemical compound C1=CC(=O)N(C)C=C1C=C(S1)C(=O)NC1=NC1=CC=CC=C1Cl QVGNNTDUNPSZJY-UHFFFAOYSA-N 0.000 claims description 2
AZRXSULNBSVQHE-UHFFFAOYSA-N 2-(2-chloroanilino)-5-[(3-chloro-4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=C(Cl)C(O)=CC=C1C=C(S1)C(=O)NC1=NC1=CC=CC=C1Cl AZRXSULNBSVQHE-UHFFFAOYSA-N 0.000 claims description 2
OVZIDDOBFQWANM-UHFFFAOYSA-N 2-(2-chloroanilino)-5-[(3-fluoro-4-methoxyphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=C(F)C(OC)=CC=C1C=C(S1)C(=O)NC1=NC1=CC=CC=C1Cl OVZIDDOBFQWANM-UHFFFAOYSA-N 0.000 claims description 2
PTIYTUSMMOTQIO-UHFFFAOYSA-N 2-(2-chloroanilino)-5-[(4-hydroxy-2-methoxyphenyl)methylidene]-1,3-thiazol-4-one Chemical compound COC1=CC(O)=CC=C1C=C(S1)C(=O)NC1=NC1=CC=CC=C1Cl PTIYTUSMMOTQIO-UHFFFAOYSA-N 0.000 claims description 2
CEYSJUACBKYCKN-UHFFFAOYSA-N 2-(2-chloroanilino)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-thiazolone Chemical compound C1=C(O)C(OC)=CC(C=C2C(N=C(NC=3C(=CC=CC=3)Cl)S2)=O)=C1 CEYSJUACBKYCKN-UHFFFAOYSA-N 0.000 claims description 2
ZRYHAXCSONNMSH-UHFFFAOYSA-N 2-(2-chloroanilino)-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=CC(O)=CC=C1C=C1C(=O)N=C(NC=2C(=CC=CC=2)Cl)S1 ZRYHAXCSONNMSH-UHFFFAOYSA-N 0.000 claims description 2
DVNYEXNJFOCAJB-UHFFFAOYSA-N 2-(2-chloroanilino)-5-[(6-methoxypyridin-3-yl)methylidene]-1,3-thiazol-4-one Chemical compound C1=NC(OC)=CC=C1C=C1C(=O)N=C(NC=2C(=CC=CC=2)Cl)S1 DVNYEXNJFOCAJB-UHFFFAOYSA-N 0.000 claims description 2
NOLPLICPHLALDC-UHFFFAOYSA-N 2-(2-chloroanilino)-5-[(6-oxo-1h-pyridin-3-yl)methylidene]-1,3-thiazol-4-one Chemical compound ClC1=CC=CC=C1N=C(NC1=O)SC1=CC1=CNC(=O)C=C1 NOLPLICPHLALDC-UHFFFAOYSA-N 0.000 claims description 2
FBVKAPKJUVAQGV-UHFFFAOYSA-N 2-(2-methoxy-6-methylanilino)-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound COC1=CC=CC(C)=C1NC(S1)=NC(=O)C1=CC1=CC=C(N=CC=C2)C2=C1 FBVKAPKJUVAQGV-UHFFFAOYSA-N 0.000 claims description 2
OLUCGVIJCPYPMP-UHFFFAOYSA-N 2-(2-methoxyanilino)-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound COC1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(N=CC=C2)C2=C1 OLUCGVIJCPYPMP-UHFFFAOYSA-N 0.000 claims description 2
RBYSUZKKJAVNEO-UHFFFAOYSA-N 2-(2-methylanilino)-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound CC1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(N=CC=C2)C2=C1 RBYSUZKKJAVNEO-UHFFFAOYSA-N 0.000 claims description 2
PIRMWBYJEUIZHC-UHFFFAOYSA-N 2-(2-nitroanilino)-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound [O-][N+](=O)C1=CC=CC=C1NC(S1)=NC(=O)C1=CC1=CC=C(N=CC=C2)C2=C1 PIRMWBYJEUIZHC-UHFFFAOYSA-N 0.000 claims description 2
KBHLLKVBFLXVNP-UHFFFAOYSA-N 2-(4-bromo-2-chloroanilino)-5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-1,3-thiazol-4-one Chemical compound ClC1=CC(Br)=CC=C1N=C(NC1=O)SC1=CC1=CC=C(OCC2)C2=C1 KBHLLKVBFLXVNP-UHFFFAOYSA-N 0.000 claims description 2
YBXFNZSFYCNPEU-UHFFFAOYSA-N 2-[(4-tert-butyl-1,3-thiazol-2-yl)amino]-5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-1,3-thiazol-4-one Chemical compound CC(C)(C)C1=CSC(NC=2SC(C(=O)N=2)=CC=2C=C3CCOC3=CC=2)=N1 YBXFNZSFYCNPEU-UHFFFAOYSA-N 0.000 claims description 2
BCJMJGLAYMJXAF-UHFFFAOYSA-N 3-chloro-4-[[5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-4-oxo-1,3-thiazol-2-yl]amino]benzoic acid Chemical compound ClC1=CC(C(=O)O)=CC=C1N=C(NC1=O)SC1=CC1=CC=C(OCC2)C2=C1 BCJMJGLAYMJXAF-UHFFFAOYSA-N 0.000 claims description 2
SVZBIZXAGNXFAT-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-ylmethylidene)-2-(2-chloroanilino)-1,3-thiazol-4-one Chemical compound ClC1=CC=CC=C1NC(S1)=NC(=O)C1=CC1=CC=C(OCO2)C2=C1 SVZBIZXAGNXFAT-UHFFFAOYSA-N 0.000 claims description 2
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QPMDWIOUHQWKHV-ODZAUARKSA-M potassium;(z)-4-hydroxy-4-oxobut-2-enoate Chemical compound [K+].OC(=O)\C=C/C([O-])=O QPMDWIOUHQWKHV-ODZAUARKSA-M 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
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238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
VUAOIXANWIFYCU-UHFFFAOYSA-N quinoline-6-carbaldehyde Chemical compound N1=CC=CC2=CC(C=O)=CC=C21 VUAOIXANWIFYCU-UHFFFAOYSA-N 0.000 description 1
238000001959 radiotherapy Methods 0.000 description 1
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230000002441 reversible effect Effects 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
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ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
230000011664 signaling Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
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238000009491 slugging Methods 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
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235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
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URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229940048181 sodium sulfide nonahydrate Drugs 0.000 description 1
ABBQHOQBGMUPJH-UHFFFAOYSA-N sodium;2-hydroxybenzoic acid Chemical compound [Na+].OC(=O)C1=CC=CC=C1O ABBQHOQBGMUPJH-UHFFFAOYSA-N 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
WMDLZMCDBSJMTM-UHFFFAOYSA-M sodium;sulfanide;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[SH-] WMDLZMCDBSJMTM-UHFFFAOYSA-M 0.000 description 1
238000000527 sonication Methods 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
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238000007920 subcutaneous administration Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
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239000000375 suspending agent Substances 0.000 description 1
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125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
229940100611 topical cream Drugs 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
229940100615 topical ointment Drugs 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
230000026683 transduction Effects 0.000 description 1
238000010361 transduction Methods 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
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238000005292 vacuum distillation Methods 0.000 description 1
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NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
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210000005253 yeast cell Anatomy 0.000 description 1
229930195724 β-lactose Natural products 0.000 description 1
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/08—Plasma substitutes; Perfusion solutions; Dialytics or haemodialytics; Drugs for electrolytic or acid-base disorders, e.g. hypovolemic shock
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—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 only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/08—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 alicyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—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 three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
Hematology (AREA)
Physical Education & Sports Medicine (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Peptides Or Proteins (AREA)
Thiazole And Isothizaole Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

OA1200500154A 2002-11-22 2003-11-18 Novel chemical compounds. OA12963A (en)

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US42838402P	2002-11-22	2002-11-22

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Country Status (30)

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US (1)	US7767701B2 (de)
EP (1)	EP1567112B1 (de)
JP (1)	JP2006509765A (de)
KR (1)	KR20050085115A (de)
CN (1)	CN100579978C (de)
AP (1)	AP1967A (de)
AR (1)	AR045407A1 (de)
AT (1)	ATE411302T1 (de)
AU (1)	AU2003298693B2 (de)
BR (1)	BR0316502A (de)
CA (1)	CA2507256A1 (de)
CY (1)	CY1108655T1 (de)
DE (1)	DE60324178D1 (de)
DK (1)	DK1567112T3 (de)
EA (1)	EA008865B1 (de)
EC (1)	ECSP055808A (de)
ES (1)	ES2315566T3 (de)
IS (1)	IS2659B (de)
MA (1)	MA27701A1 (de)
MX (1)	MXPA05005406A (de)
MY (1)	MY140132A (de)
NO (1)	NO20052928L (de)
NZ (1)	NZ539873A (de)
OA (1)	OA12963A (de)
PL (1)	PL377564A1 (de)
PT (1)	PT1567112E (de)
SI (1)	SI1567112T1 (de)
TW (1)	TWI309648B (de)
UA (1)	UA80572C2 (de)
WO (1)	WO2004047760A2 (de)

Families Citing this family (36)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MXPA04005939A (es)	2002-01-22	2005-01-25	Warner Lambert Co	2-(piridin-2-ilamino)-pirido[2,3-d]pirimidin-7-onas.
AU2004255934B2 (en) *	2003-07-11	2010-02-25	Warner-Lambert Company Llc	Isethionate salt of a selective CDK4 inhibitor
ES2328146T3 (es) *	2003-07-28	2009-11-10	Merck Serono Sa	2-imino-4-(tio)oxo-5-policiclovinilazolinas para su uso como inhibidores de p13 quinasas.
USRE43833E1 (en)	2003-11-21	2012-11-27	Actelion Pharmaceuticals Ltd.	Thiazolidin-4-one derivatives
USRE43728E1 (en)	2003-11-21	2012-10-09	Actelion Pharmaceuticals Ltd.	Thiazolidin-4-one derivatives
EP1718642A4 (de) *	2004-02-25	2010-11-24	Glaxosmithkline Llc	Neue chemische verbindungen
AR050253A1 (es)	2004-06-24	2006-10-11	Smithkline Beecham Corp	Compuesto derivado de indazol carboxamida, composicion que lo comprende y su uso para la preparacion de un medicamento
ES2317238T3 (es) *	2004-07-01	2009-04-16	F. Hoffmann-La Roche Ag	Quinolina-tiazolinonas con actividad antiproliferante cdk-1.
MXPA06015028A (es)	2004-07-01	2007-02-08	Hoffmann La Roche	Tiazolinas cinolinas no sustituidas.
US7253285B2 (en)	2004-09-17	2007-08-07	Hoffmann-La Roche Inc.	Thiazolinone 4-monosubstituted quinolines
US7241893B2 (en) *	2004-09-17	2007-07-10	Hoffman-La Roche Inc.	Thiazolinone 2-substituted quinolines
ZA200702435B (en) *	2004-10-12	2008-06-25	Serono Lab	PI3 Kinase gamma inhibitors for the treatment of anaemia
US7268231B2 (en)	2004-10-14	2007-09-11	Hoffmann-La Roche Inc.	1,5-Naphthyridine azolinone
KR100875870B1 (ko) *	2004-10-14	2008-12-26	에프. 호프만-라 로슈 아게	항암제로서의 신규 아자인돌 티아졸리논
CN101039939B (zh) *	2004-10-14	2010-07-07	霍夫曼-拉罗奇有限公司	作为cdk1抑制剂的喹唑啉基亚甲基噻唑啉酮类
US7304074B2 (en) *	2005-04-05	2007-12-04	Hoffmann-La Roche Inc.	Substituted 1,5-naphthyridine azolinones
TW200716132A (en) *	2005-05-03	2007-05-01	Smithkline Beecham Corp	Novel chemical compounds
US20090203692A1 (en) *	2005-05-23	2009-08-13	Smithkline Beecham Corporation	Novel chemical compounds
JP2008543769A (ja) *	2005-06-08	2008-12-04	スミスクライン・ビーチャム・コーポレイション	（５ｚ）−５−（６−キノキサリニルメチリデン）−２−［（２，４，６−トリクロロフェニル）アミノ］−１，３−チアゾール−４（５ｈ）−オン
PE20070083A1 (es) *	2005-06-08	2007-01-27	Smithkline Beecham Corp	(5z)-5-(6-quinoxalinilmetilideno)-2-[(2,6-diclorofenil)amino]-1,3-tiazol-4(5h)-ona
TW200745066A (en)	2005-09-16	2007-12-16	Torrent Pharmaceuticals Ltd	Novel PTP1B inhibitors
JP2009514984A (ja) *	2005-11-08	2009-04-09	スミスクライン・ビーチャム・コーポレイション	新規化合物
JP2009528383A (ja) *	2006-03-02	2009-08-06	スミスクライン・ビーチャム・コーポレイション	Ｐｉ３キナーゼ阻害剤として用いるためのチアゾロン
WO2007103758A2 (en) *	2006-03-02	2007-09-13	Smithkline Beecham Corporation	Thiazolones for use as pi3 kinase inhibitors
KR100752757B1 (ko) *	2006-04-05	2007-08-29	한국과학기술연구원	2-페닐이미노-1,3-티아졸린을 포함하는 미백 조성물
MX2008013668A (es) *	2006-04-25	2009-01-27	Cleveland Clinic Foundation	Agentes antivirales que activan la arnasa l.
TWI460166B (zh) *	2006-11-23	2014-11-11	Actelion Pharmaceuticals Ltd	製備２-亞胺基-四氫噻唑-４-酮衍生物之新穎方法
US8912340B2 (en)	2006-11-23	2014-12-16	Actelion Pharmaceuticals Ltd.	Process for the preparation of 2-imino-thiazolidin-4-one derivatives
US20100286041A1 (en) *	2007-03-22	2010-11-11	Smithkline Beecham Corporation	(5z)-5-(6-quinoxalinylmethylidene)-2-[(2,6-dichlorophenyl)amino]-1,3-thiazol-4(5h)-one
CN101274918A (zh) *	2007-03-30	2008-10-01	中国科学院上海药物研究所	一类取代五元杂环化合物,其制备方法和医学用途
WO2010122979A1 (ja)	2009-04-20	2010-10-28	Ｓｂｉバイオテック株式会社	チアゾリジノン誘導体
US9745323B2 (en)	2012-07-30	2017-08-29	Kyoto University	Compound and pharmaceutical composition for neuropsychological disorder or malignant tumor
SMT202000298T1 (it)	2012-08-17	2020-07-08	Actelion Pharmaceuticals Ltd	Processo per la produzione di (2z,5z)-5-(3-cloro-4((r)-2,3-diidrossipropossi) benziliden)-2-(propilimmino)-3-(o-tolil)tiazolidin-4-one e intermedio usato in detto processo
RU2521390C1 (ru) *	2013-03-14	2014-06-27	Общество с ограниченной ответственностью "Тиацен"	Производное роданина и средство для профилактики опухолевых заболеваний
PL3148990T3 (pl) *	2014-05-28	2022-05-30	Universität Bern	Związki tiazolidynonu i ich zastosowanie w leczeniu zaburzeń psychiatrycznych neurologicznych i stanów zapalnych, w szczególności stanów zapalnych układu nerwowego
CN104370852B (zh) *	2014-11-26	2016-04-20	山东大学	一种噻唑烷酮类化合物及其在制备治疗铁紊乱相关疾病药物中的应用

Family Cites Families (44)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1604530A (de) *	1967-06-06	1971-11-29
JPS5545648A (en)	1978-09-29	1980-03-31	Teikoku Hormone Mfg Co Ltd	2-formyldibenzazepin derivative and its preparation
HU188852B (en) *	1983-03-16	1986-05-28	Richter Gedeon Vegyeszeti Gyar Rt,Hu	Process for producing thiazolidine derivatives active against gastric ulcer and intestinal ulcer
SU1611216A3 (ru) *	1986-12-29	1990-11-30	Пфайзер Инк (Фирма)	Способ получени производных тиазолидиндиона или их фармацевтически приемлемых солей с щелочными металлами
US4971996A (en)	1987-03-11	1990-11-20	Kanegafuchi Kagaku Kogyo Kabushiki Kaisha	Hydroxystyrene compounds which are useful as tyrosine kinase inhibitors
JPH0197926A (ja)	1987-10-09	1989-04-17	Idemitsu Kosan Co Ltd	有機非線型光学材料
DD270072A1 (de)	1988-03-14	1989-07-19	Univ Halle Wittenberg	Verfahren zur herstellung von 5-aryliden- hoch 2-thiazolin-4-onen
US5306822A (en)	1988-05-25	1994-04-26	Warner-Lambert Company	Arylmethylenyl derivatives of oxazolidinone
US5145753A (en)	1989-09-12	1992-09-08	Mitsubishi Jukogyo Kabushiki Kaisha	Solid electrolyte fuel cell
US5053420A (en)	1989-10-13	1991-10-01	Pershadsingh Harrihar A	Thiazolidine derivatives for the treatment of hypertension
GB9004483D0 (en)	1990-02-28	1990-04-25	Erba Carlo Spa	New aryl-and heteroarylethenylene derivatives and process for their preparation
US5143928A (en)	1990-03-27	1992-09-01	Warner-Lambert Company	3,5-di-tertiarybutyl-4-hydroxyphenylmethylene derivatives of 2-substituted thiazolidinones, oxazolidinones, and imidazolidinones as antiinflammatory agents
JPH052200A (ja)	1990-09-28	1993-01-08	Toshiba Corp	有機非線形光学材料
CA2444071C (en) *	1991-02-08	2008-10-07	Wellstat Therapeutics Corporation	Oxypurine nucleosides and their congeners, and acyl derivatives thereof, for improvement of hematopoiesis
JP3155050B2 (ja)	1991-02-28	2001-04-09	富士通株式会社	荷電粒子ビームを用いた露光方法
EP0554834B1 (de)	1992-02-03	1998-06-03	Fuji Photo Film Co., Ltd.	Verfahren zur Dispergierung eines Farbstoffs und ein Farbstoff enthaltendes photographisches Silberhalogenidmaterial
JP2835246B2 (ja)	1992-06-02	1998-12-14	富士写真フイルム株式会社	ハロゲン化銀写真感光材料
NZ248573A (en)	1992-09-10	1996-02-27	Lilly Co Eli	5-arylmethyl (and methylidene) thiazolidin-4-one derivatives; their preparation and pharmaceutical compositions
EP0587230B1 (de)	1992-09-11	2003-11-26	Agfa-Gevaert	Photographisches Element,das einen Filterfarbstoff enthält, für Schnellverarbeitungs-Verwendungen
EP0587229B1 (de)	1992-09-11	2002-05-08	Agfa-Gevaert	Photographisches Element,das einen Filterfarbstoff enthält, für Schnellverarbeitungs-Verwendungen
JPH06128234A (ja)	1992-10-19	1994-05-10	Fuji Photo Film Co Ltd	不斉炭素原子を有する化合物およびそれからなる非線形光学材料
US5554767A (en)	1993-05-21	1996-09-10	Warner-Lambert Company	Alpha-mercaptoacrylic acid derivatives having calpain inhibitory activity
US6251928B1 (en)	1994-03-16	2001-06-26	Eli Lilly And Company	Treatment of alzheimer's disease employing inhibitors of cathepsin D
JP3871354B2 (ja)	1994-07-29	2007-01-24	株式会社フジモト・コーポレーション	新規な２−（ｎ−シアノイミノ）チアゾリジン−４−オン誘導体
JPH08109176A (ja)	1994-10-07	1996-04-30	Torii Yakuhin Kk	イソローダニンｎ酢酸誘導体
IL117208A0 (en)	1995-02-23	1996-06-18	Nissan Chemical Ind Ltd	Indole type thiazolidines
JP3923079B2 (ja) *	1995-07-31	2007-05-30	塩野義製薬株式会社	ホスホリパーゼａ２阻害活性を有するピロリジン誘導体
US5618835A (en)	1996-02-01	1997-04-08	The Procter & Gamble Company	Dihydrobenzofuran and related compounds useful as anti-inflammatory agents
JPH09255669A (ja)	1996-03-22	1997-09-30	Hisamitsu Pharmaceut Co Inc	新規なベンジリデン誘導体
US5958957A (en)	1996-04-19	1999-09-28	Novo Nordisk A/S	Modulators of molecules with phosphotyrosine recognition units
UY24886A1 (es)	1997-02-18	2001-08-27	Smithkline Beecham Plc	Tiazolidindiona
US6011031A (en)	1997-05-30	2000-01-04	Dr. Reddy's Research Foundation	Azolidinediones useful for the treatment of diabetes, dyslipidemia and hypertension: process for their preparation and pharmaceutical compositions containing them
US6211209B1 (en) *	1997-08-08	2001-04-03	Warner-Lambert Company	Method of inhibiting connective tissue degradation
WO1999059586A1 (en)	1998-05-19	1999-11-25	Regents Of The University Of California	Thiazolidine and oxazolidine derivatives for the treatment of acute myocardial infarction and inhibition of cardiomyocyte apoptosis
WO2000018748A1 (en)	1998-09-30	2000-04-06	Roche Diagnostics Gmbh	Rhodanine derivatives for the treatment and prevention of metabolic bone disorders
US6221613B1 (en)	1998-12-31	2001-04-24	Synaptic Pharmaceutical Corporation	DNA encoding a human melanin concentrating hormone receptor (MCH1) and uses thereof
US6689491B1 (en)	1999-02-08	2004-02-10	Fuji Photo Film Co., Ltd.	Luminescent device material, luminescent device using the same, and amine compound
WO2001002394A1 (en)	1999-07-01	2001-01-11	Geron Corporation	Substituted indole compounds and their use for the treatment of cancer
JP2001348520A (ja)	2000-04-03	2001-12-18	Fuji Photo Film Co Ltd	メチン化合物、固体微粒子分散物、インクジェット用記録液、およびインクジェット記録方法
EP1299362A4 (de)	2000-07-05	2004-11-03	Synaptic Pharma Corp	Selektive rezeptorantagonisten des melaninkonzentrierenden hormons-1 (mch1) und ihre anwendung
US6410734B1 (en)	2000-07-17	2002-06-25	Wyeth	2-substituted thiazolidinones as beta-3 adrenergic receptor agonists
DE10115227A1 (de)	2001-03-28	2002-12-19	Bayer Ag	Optischer Datenträger enthaltend in der Informationsschicht eine lichtabsorbierende Verbindung mit mehreren chromophoren Zentren
US6452014B1 (en)	2000-12-22	2002-09-17	Geron Corporation	Telomerase inhibitors and methods of their use
AR037714A1 (es)	2001-12-06	2004-12-01	Maxia Pharmaceuticals Inc	Derivados de tiazolidinona y oxazolidinona 2-sustituidos para la inhibicion de fosfatasas y el tratamiento de cancer

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Also Published As

Publication number	Publication date
EP1567112A2 (de)	2005-08-31
WO2004047760A2 (en)	2004-06-10
PT1567112E (pt)	2009-01-08
AR045407A1 (es)	2005-10-26
AP2005003304A0 (en)	2005-06-30
AP1967A (en)	2009-03-10
BR0316502A (pt)	2005-10-04
PL377564A1 (pl)	2006-02-06
CY1108655T1 (el)	2014-04-09
IS7879A (is)	2005-06-02
IS2659B (is)	2010-08-15
NO20052928D0 (no)	2005-06-15
KR20050085115A (ko)	2005-08-29
ATE411302T1 (de)	2008-10-15
AU2003298693B2 (en)	2010-09-30
DE60324178D1 (de)	2008-11-27
NO20052928L (no)	2005-08-17
NZ539873A (en)	2008-09-26
EP1567112A4 (de)	2006-11-15
US7767701B2 (en)	2010-08-03
MXPA05005406A (es)	2005-08-03
SI1567112T1 (sl)	2009-02-28
CN100579978C (zh)	2010-01-13
DK1567112T3 (da)	2009-02-09
ECSP055808A (es)	2005-09-20
JP2006509765A (ja)	2006-03-23
EP1567112B1 (de)	2008-10-15
EA008865B1 (ru)	2007-08-31
TWI309648B (en)	2009-05-11
MY140132A (en)	2009-11-30
MA27701A1 (fr)	2006-01-02
UA80572C2 (en)	2007-10-10
US20060293338A1 (en)	2006-12-28
HK1083443A1 (en)	2006-07-07
CA2507256A1 (en)	2004-06-10
WO2004047760A3 (en)	2004-10-21
EA200500856A1 (ru)	2005-10-27
CN1742010A (zh)	2006-03-01
AU2003298693A1 (en)	2004-06-18
TW200418819A (en)	2004-10-01
ES2315566T3 (es)	2009-04-01

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