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
MJEOOEQTXHSDKO-UHFFFAOYSA-N 5-(2,1,3-benzothiadiazol-5-ylmethylidene)-2-(2-chloro-5-fluoroanilino)-1,3-thiazol-4-one Chemical compound FC1=CC=C(Cl)C(N=C2SC(C(=O)N2)=CC2=CC3=NSN=C3C=C2)=C1 MJEOOEQTXHSDKO-UHFFFAOYSA-N 0.000 claims description 2
GYOFCYHSKUCRQZ-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-(2,4,6-trimethylanilino)-1,3-thiazol-4-one Chemical compound CC1=CC(C)=CC(C)=C1N=C(NC1=O)SC1=CC1=CC=C(OCC2)C2=C1 GYOFCYHSKUCRQZ-UHFFFAOYSA-N 0.000 claims description 2
VYNWEIBKZBBVJX-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-(2-methylanilino)-1,3-thiazol-4-one Chemical compound CC1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(OCC2)C2=C1 VYNWEIBKZBBVJX-UHFFFAOYSA-N 0.000 claims description 2
WEYQVIXVEQEUIU-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-(2-methylsulfanylanilino)-1,3-thiazol-4-one Chemical compound CSC1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(OCC2)C2=C1 WEYQVIXVEQEUIU-UHFFFAOYSA-N 0.000 claims description 2
UKBZERKCSICJCY-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-(2-methylsulfinylanilino)-1,3-thiazol-4-one Chemical compound CS(=O)C1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(OCC2)C2=C1 UKBZERKCSICJCY-UHFFFAOYSA-N 0.000 claims description 2
IAYSASOKGMRVCF-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-[2-(dimethylamino)ethylamino]-1,3-thiazol-4-one Chemical compound S1C(NCCN(C)C)=NC(=O)C1=CC1=CC=C(OCC2)C2=C1 IAYSASOKGMRVCF-UHFFFAOYSA-N 0.000 claims description 2
IXIZMBMCSXPLMU-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-[3-(dimethylamino)propylamino]-1,3-thiazol-4-one Chemical compound S1C(NCCCN(C)C)=NC(=O)C1=CC1=CC=C(OCC2)C2=C1 IXIZMBMCSXPLMU-UHFFFAOYSA-N 0.000 claims description 2
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 2
239000005711 Benzoic acid Substances 0.000 claims description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
ZNBKMGSOEFOPFL-UHFFFAOYSA-N 2-[2-chloro-5-(trifluoromethyl)anilino]-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound FC(F)(F)C1=CC=C(Cl)C(N=C2SC(C(=O)N2)=CC=2C=C3C=CC=NC3=CC=2)=C1 ZNBKMGSOEFOPFL-UHFFFAOYSA-N 0.000 claims 4
LXPBNJBMBSTCBK-UHFFFAOYSA-N 2-[(2,6-difluoroanilino)methylidene]-5-(quinolin-6-ylmethylidene)-1,3-thiazolidin-4-one Chemical compound FC1=CC=CC(F)=C1NC=C(NC1=O)SC1=CC1=CC=C(N=CC=C2)C2=C1 LXPBNJBMBSTCBK-UHFFFAOYSA-N 0.000 claims 3
238000004519 manufacturing process Methods 0.000 claims 3
CJXKRXBAWWCSQH-UHFFFAOYSA-N 2-(2-bromoanilino)-5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-1,3-thiazol-4-one Chemical compound BrC1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(OCC2)C2=C1 CJXKRXBAWWCSQH-UHFFFAOYSA-N 0.000 claims 2
KHPOVQBGFLBLBZ-UHFFFAOYSA-N 2-(2-bromoanilino)-5-[[3-(4-methylphenyl)-2,1-benzoxazol-5-yl]methylidene]-1,3-thiazol-4-one Chemical compound C1=CC(C)=CC=C1C1=C2C=C(C=C3C(N=C(NC=4C(=CC=CC=4)Br)S3)=O)C=CC2=NO1 KHPOVQBGFLBLBZ-UHFFFAOYSA-N 0.000 claims 2
VJAHLUZNTNLKQU-UHFFFAOYSA-N 2-(2-chloro-4-fluoro-5-methylanilino)-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound C1=C(F)C(C)=CC(N=C2SC(C(=O)N2)=CC=2C=C3C=CC=NC3=CC=2)=C1Cl VJAHLUZNTNLKQU-UHFFFAOYSA-N 0.000 claims 2
YOXHGYVOEADWIF-UHFFFAOYSA-N 2-(2-chloro-5-fluoroanilino)-5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-1,3-thiazol-4-one Chemical compound FC1=CC=C(Cl)C(N=C2SC(C(=O)N2)=CC=2C=C3CCOC3=CC=2)=C1 YOXHGYVOEADWIF-UHFFFAOYSA-N 0.000 claims 2
YWCUQXVCWZJPFY-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)anilino]-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound ClC1=CC(C(F)(F)F)=CC=C1N=C(NC1=O)SC1=CC1=CC=C(N=CC=C2)C2=C1 YWCUQXVCWZJPFY-UHFFFAOYSA-N 0.000 claims 2
LMOFTKZIXDCKHL-UHFFFAOYSA-N 2-[4-(methylsulfonylmethyl)anilino]-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound C1=CC(CS(=O)(=O)C)=CC=C1NC(S1)=NC(=O)C1=CC1=CC=C(N=CC=C2)C2=C1 LMOFTKZIXDCKHL-UHFFFAOYSA-N 0.000 claims 2
QMTFHSFHCNURTF-UHFFFAOYSA-N 2-[4-[(4-methylpiperazin-1-yl)methyl]anilino]-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1NC(S1)=NC(=O)C1=CC1=CC=C(N=CC=C2)C2=C1 QMTFHSFHCNURTF-UHFFFAOYSA-N 0.000 claims 2
RTKYDPGKYSVFFT-UHFFFAOYSA-N 3-[[4-oxo-5-(quinolin-6-ylmethylidene)-1,3-thiazol-2-yl]amino]benzamide Chemical compound NC(=O)C1=CC=CC(NC=2SC(C(=O)N=2)=CC=2C=C3C=CC=NC3=CC=2)=C1 RTKYDPGKYSVFFT-UHFFFAOYSA-N 0.000 claims 2
KXGHSOUKRYJHGW-UHFFFAOYSA-N 3-[[4-oxo-5-(quinolin-6-ylmethylidene)-1,3-thiazol-2-yl]amino]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(NC=2SC(C(=O)N=2)=CC=2C=C3C=CC=NC3=CC=2)=C1 KXGHSOUKRYJHGW-UHFFFAOYSA-N 0.000 claims 2
VXJSCDKCPNETQI-UHFFFAOYSA-N 4-chloro-3-[[4-oxo-5-(quinolin-6-ylmethylidene)-1,3-thiazol-2-yl]amino]benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C(N=C2SC(C(=O)N2)=CC=2C=C3C=CC=NC3=CC=2)=C1 VXJSCDKCPNETQI-UHFFFAOYSA-N 0.000 claims 2
IIHXDPRLFRZEQG-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-(2-methoxyanilino)-1,3-thiazol-4-one Chemical compound COC1=CC=CC=C1NC(S1)=NC(=O)C1=CC1=CC=C(OCC2)C2=C1 IIHXDPRLFRZEQG-UHFFFAOYSA-N 0.000 claims 2
NYSIWPJIULZPCZ-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-(3-imidazol-1-ylpropylamino)-1,3-thiazol-4-one Chemical compound S1C(=CC=2C=C3CCOC3=CC=2)C(=O)N=C1NCCCN1C=CN=C1 NYSIWPJIULZPCZ-UHFFFAOYSA-N 0.000 claims 2
BLTWRBXFEIHSMD-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-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(OCC2)C2=C1 BLTWRBXFEIHSMD-UHFFFAOYSA-N 0.000 claims 2
CLAUYFUUESHZGI-UHFFFAOYSA-N 5-(quinolin-6-ylmethylidene)-2-(2,4,6-trimethylanilino)-1,3-thiazol-4-one Chemical compound CC1=CC(C)=CC(C)=C1N=C(NC1=O)SC1=CC1=CC=C(N=CC=C2)C2=C1 CLAUYFUUESHZGI-UHFFFAOYSA-N 0.000 claims 2
LYHOFPRPWDSAAB-UHFFFAOYSA-N methyl 3-chloro-4-[[5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-4-oxo-1,3-thiazol-2-yl]amino]benzoate Chemical compound ClC1=CC(C(=O)OC)=CC=C1N=C(NC1=O)SC1=CC1=CC=C(OCC2)C2=C1 LYHOFPRPWDSAAB-UHFFFAOYSA-N 0.000 claims 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 2
YPNYHCTVVNRGFU-UHFFFAOYSA-N 2-(2,6-dichloroanilino)-5-(1h-pyrrolo[2,3-b]pyridin-2-ylmethylidene)-1,3-thiazol-4-one Chemical compound ClC1=CC=CC(Cl)=C1NC(S1)=NC(=O)C1=CC1=CC2=CC=CN=C2N1 YPNYHCTVVNRGFU-UHFFFAOYSA-N 0.000 claims 1
RBMYZLOAIMVAJF-UHFFFAOYSA-N 2-(2,6-dichloroanilino)-5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-1,3-thiazol-4-one Chemical compound ClC1=CC=CC(Cl)=C1N=C(NC1=O)SC1=CC1=CC=C(OCC2)C2=C1 RBMYZLOAIMVAJF-UHFFFAOYSA-N 0.000 claims 1
YEBLRTZBIRRDLW-UHFFFAOYSA-N 2-[2-(3-chlorophenyl)ethylamino]-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound ClC1=CC=CC(CCNC=2SC(C(=O)N=2)=CC=2C=C3C=CC=NC3=CC=2)=C1 YEBLRTZBIRRDLW-UHFFFAOYSA-N 0.000 claims 1
URGRVVMIWYGKLP-UHFFFAOYSA-N 2-[3-(methylsulfonylmethyl)anilino]-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound CS(=O)(=O)CC1=CC=CC(NC=2SC(C(=O)N=2)=CC=2C=C3C=CC=NC3=CC=2)=C1 URGRVVMIWYGKLP-UHFFFAOYSA-N 0.000 claims 1
WKXDUMMKYUVSQW-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(S1)=NC(=O)C1=CC1=CC=C(N=CC=C2)C2=C1 WKXDUMMKYUVSQW-UHFFFAOYSA-N 0.000 claims 1
AGJORFGENDORBO-UHFFFAOYSA-N 4-[[4-oxo-5-(quinolin-6-ylmethylidene)-1,3-thiazol-2-yl]amino]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1NC(S1)=NC(=O)C1=CC1=CC=C(N=CC=C2)C2=C1 AGJORFGENDORBO-UHFFFAOYSA-N 0.000 claims 1
AWLUKGDKBKLSAP-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-(2-nitroanilino)-1,3-thiazol-4-one Chemical compound [O-][N+](=O)C1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(OCC2)C2=C1 AWLUKGDKBKLSAP-UHFFFAOYSA-N 0.000 claims 1
ZHUMEWPDPSQSSS-UHFFFAOYSA-N 5-[[2-(2-chloroanilino)-4-oxo-1,3-thiazol-5-ylidene]methyl]-3h-1,3-benzoxazol-2-one Chemical compound ClC1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(OC(=O)N2)C2=C1 ZHUMEWPDPSQSSS-UHFFFAOYSA-N 0.000 claims 1
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
229960004365 benzoic acid Drugs 0.000 claims 1
KAPWTUNBBNKNKW-UHFFFAOYSA-N n'-[5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-4-oxo-1,3-thiazol-2-yl]benzohydrazide Chemical compound N=1C(=O)C(=CC=2C=C3CCOC3=CC=2)SC=1NNC(=O)C1=CC=CC=C1 KAPWTUNBBNKNKW-UHFFFAOYSA-N 0.000 claims 1
238000000034 method Methods 0.000 abstract description 29
102000004169 proteins and genes Human genes 0.000 abstract description 14
108090000623 proteins and genes Proteins 0.000 abstract description 14
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 178
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 104
238000005160 1H NMR spectroscopy Methods 0.000 description 101
239000000203 mixture Substances 0.000 description 59
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
239000007787 solid Substances 0.000 description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
239000000243 solution Substances 0.000 description 23
235000002639 sodium chloride Nutrition 0.000 description 15
210000004027 cell Anatomy 0.000 description 14
238000009472 formulation Methods 0.000 description 14
150000003839 salts Chemical class 0.000 description 14
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 14
239000000843 powder Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 12
238000004128 high performance liquid chromatography Methods 0.000 description 12
238000001819 mass spectrum Methods 0.000 description 12
206010028980 Neoplasm Diseases 0.000 description 11
238000001914 filtration Methods 0.000 description 10
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
201000011510 cancer Diseases 0.000 description 9
239000003814 drug Substances 0.000 description 9
230000008569 process Effects 0.000 description 9
238000010992 reflux Methods 0.000 description 9
239000000725 suspension Substances 0.000 description 9
239000003826 tablet Substances 0.000 description 9
229940079593 drug Drugs 0.000 description 8
239000000047 product Substances 0.000 description 8
238000011282 treatment Methods 0.000 description 8
108091007914 CDKs Proteins 0.000 description 7
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 6
208000017667 Chronic Disease Diseases 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000003921 oil Substances 0.000 description 6
108090000765 processed proteins & peptides Proteins 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
102100023114 Dual specificity tyrosine-phosphorylation-regulated kinase 3 Human genes 0.000 description 5
102100032826 Homeodomain-interacting protein kinase 3 Human genes 0.000 description 5
101001049991 Homo sapiens Dual specificity tyrosine-phosphorylation-regulated kinase 3 Proteins 0.000 description 5
101001066389 Homo sapiens Homeodomain-interacting protein kinase 3 Proteins 0.000 description 5
230000005784 autoimmunity Effects 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
239000007788 liquid Substances 0.000 description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
240000004808 Saccharomyces cerevisiae Species 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000000576 coating method Methods 0.000 description 4
239000006071 cream Substances 0.000 description 4
239000008187 granular material Substances 0.000 description 4
238000011065 in-situ storage Methods 0.000 description 4
239000000314 lubricant Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
239000008107 starch Substances 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
102000054300 EC 2.7.11.- Human genes 0.000 description 3
108700035490 EC 2.7.11.- Proteins 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
229910004373 HOAc Inorganic materials 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 3
238000003556 assay Methods 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
238000002512 chemotherapy Methods 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
239000011248 coating agent Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
208000035475 disorder Diseases 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
230000003394 haemopoietic effect Effects 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
239000006072 paste Substances 0.000 description 3
230000026731 phosphorylation Effects 0.000 description 3
238000006366 phosphorylation reaction Methods 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
230000019491 signal transduction Effects 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000000758 substrate Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
210000001519 tissue Anatomy 0.000 description 3
238000011200 topical administration Methods 0.000 description 3
239000001993 wax Substances 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
KISWVXRQTGLFGD-UHFFFAOYSA-N 2-[[2-[[6-amino-2-[[2-[[2-[[5-amino-2-[[2-[[1-[2-[[6-amino-2-[(2,5-diamino-5-oxopentanoyl)amino]hexanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-(diaminomethylideneamino)p Chemical compound C1CCN(C(=O)C(CCCN=C(N)N)NC(=O)C(CCCCN)NC(=O)C(N)CCC(N)=O)C1C(=O)NC(CO)C(=O)NC(CCC(N)=O)C(=O)NC(CCCN=C(N)N)C(=O)NC(CO)C(=O)NC(CCCCN)C(=O)NC(C(=O)NC(CC(C)C)C(O)=O)CC1=CC=C(O)C=C1 KISWVXRQTGLFGD-UHFFFAOYSA-N 0.000 description 2
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 2
ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
102000008130 Cyclic AMP-Dependent Protein Kinases Human genes 0.000 description 2
102000016736 Cyclin Human genes 0.000 description 2
108050006400 Cyclin Proteins 0.000 description 2
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
239000006144 Dulbecco’s modiﬁed Eagle's medium Substances 0.000 description 2
102000005720 Glutathione transferase Human genes 0.000 description 2
108010070675 Glutathione transferase Proteins 0.000 description 2
101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 2
108010001336 Horseradish Peroxidase Proteins 0.000 description 2
102100032535 L-seryl-tRNA(Sec) kinase Human genes 0.000 description 2
101710088843 L-seryl-tRNA(Sec) kinase Proteins 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
102100033254 Tumor suppressor ARF Human genes 0.000 description 2
235000010419 agar Nutrition 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
239000008112 carboxymethyl-cellulose Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000003086 colorant Substances 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
230000001351 cycling effect Effects 0.000 description 2
238000000132 electrospray ionisation Methods 0.000 description 2
210000003013 erythroid precursor cell Anatomy 0.000 description 2
IWUXJCHIHHGRFR-UHFFFAOYSA-N ethanethioamide;hydrochloride Chemical compound Cl.CC(N)=S IWUXJCHIHHGRFR-UHFFFAOYSA-N 0.000 description 2
239000012467 final product Substances 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
239000006260 foam Substances 0.000 description 2
235000013355 food flavoring agent Nutrition 0.000 description 2
239000000499 gel Substances 0.000 description 2
RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
230000003834 intracellular effect Effects 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
150000002540 isothiocyanates Chemical class 0.000 description 2
239000002502 liposome Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
230000001404 mediated effect Effects 0.000 description 2
238000002156 mixing Methods 0.000 description 2
DQMWMUMCNOJLSI-UHFFFAOYSA-N n-carbamothioylbenzamide Chemical compound NC(=S)NC(=O)C1=CC=CC=C1 DQMWMUMCNOJLSI-UHFFFAOYSA-N 0.000 description 2
239000002674 ointment Substances 0.000 description 2
ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
230000001105 regulatory effect Effects 0.000 description 2
KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000007921 spray Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
235000000346 sugar Nutrition 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
230000007704 transition Effects 0.000 description 2
125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 2
239000002691 unilamellar liposome Substances 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
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 1
AWPKXPUZILRUDJ-UHFFFAOYSA-N (2,6-difluorophenyl)thiourea Chemical compound NC(=S)NC1=C(F)C=CC=C1F AWPKXPUZILRUDJ-UHFFFAOYSA-N 0.000 description 1
GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
ODUZJBKKYBQIBX-UHFFFAOYSA-N 2,6-difluoroaniline Chemical compound NC1=C(F)C=CC=C1F ODUZJBKKYBQIBX-UHFFFAOYSA-N 0.000 description 1
BBXNBCLPBOSLIR-UHFFFAOYSA-N 2-(2-methoxy-6-methylanilino)-5-[(6-oxo-1h-pyridin-3-yl)methylidene]-1,3-thiazol-4-one Chemical compound COC1=CC=CC(C)=C1NC(S1)=NC(=O)C1=CC1=CNC(=O)C=C1 BBXNBCLPBOSLIR-UHFFFAOYSA-N 0.000 description 1
125000000301 2-(3-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
OJSNJDIKPXJLER-UHFFFAOYSA-N 2-(benzylamino)-5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-1,3-thiazol-4-one Chemical compound S1C(=CC=2C=C3CCOC3=CC=2)C(=O)N=C1NCC1=CC=CC=C1 OJSNJDIKPXJLER-UHFFFAOYSA-N 0.000 description 1
BQSAXVDWXNYZHS-UHFFFAOYSA-N 2-[2,4-dichloro-5-(2-methoxyethoxy)anilino]-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound C1=C(Cl)C(OCCOC)=CC(N=C2SC(C(=O)N2)=CC=2C=C3C=CC=NC3=CC=2)=C1Cl BQSAXVDWXNYZHS-UHFFFAOYSA-N 0.000 description 1
NZZJGWOUWVLUTP-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)anilino]-5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-1,3-thiazol-4-one Chemical compound ClC1=CC(C(F)(F)F)=CC=C1N=C(NC1=O)SC1=CC1=CC=C(OCC2)C2=C1 NZZJGWOUWVLUTP-UHFFFAOYSA-N 0.000 description 1
VWUFOZAFKYOZJB-UHFFFAOYSA-N 2-chloro-5-fluoroaniline Chemical compound NC1=CC(F)=CC=C1Cl VWUFOZAFKYOZJB-UHFFFAOYSA-N 0.000 description 1
KWIXNFOTNVKIGM-UHFFFAOYSA-N 2-chloro-5-nitroaniline Chemical compound NC1=CC([N+]([O-])=O)=CC=C1Cl KWIXNFOTNVKIGM-UHFFFAOYSA-N 0.000 description 1
YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
ALKYHXVLJMQRLQ-UHFFFAOYSA-M 3-carboxynaphthalen-2-olate Chemical compound C1=CC=C2C=C(C([O-])=O)C(O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-M 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
RIGCHTPIPGOSMZ-UHFFFAOYSA-N 4-[[[5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-4-oxo-1,3-thiazol-2-yl]amino]methyl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CNC(S1)=NC(=O)C1=CC1=CC=C(OCC2)C2=C1 RIGCHTPIPGOSMZ-UHFFFAOYSA-N 0.000 description 1
PECKLIXQHBFLKD-UHFFFAOYSA-N 4-amino-5h-1,3-thiazol-2-one Chemical compound NC1=NC(=O)SC1 PECKLIXQHBFLKD-UHFFFAOYSA-N 0.000 description 1
229960000549 4-dimethylaminophenol Drugs 0.000 description 1
HLPBVILXCXEBDO-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-ylmethylidene)-2-(2-bromoanilino)-1,3-thiazol-4-one Chemical compound BrC1=CC=CC=C1NC(S1)=NC(=O)C1=CC1=CC=C(OCO2)C2=C1 HLPBVILXCXEBDO-UHFFFAOYSA-N 0.000 description 1
BKNFIEUDGAGBEV-UHFFFAOYSA-N 5-(2,1,3-benzothiadiazol-5-ylmethylidene)-2-(2-bromoanilino)-1,3-thiazol-4-one Chemical compound BrC1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC2=NSN=C2C=C1 BKNFIEUDGAGBEV-UHFFFAOYSA-N 0.000 description 1
MYSFMQDHUPZJSW-UHFFFAOYSA-N 5-(2,1,3-benzothiadiazol-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=NSN=C2C=C1 MYSFMQDHUPZJSW-UHFFFAOYSA-N 0.000 description 1
SOSZGECNJCGYTG-UHFFFAOYSA-N 5-[(3-fluoro-4-hydroxyphenyl)methylidene]-2-(2-methylanilino)-1,3-thiazol-4-one Chemical compound CC1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(O)C(F)=C1 SOSZGECNJCGYTG-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
229920000936 Agarose Polymers 0.000 description 1
102000009027 Albumins Human genes 0.000 description 1
108010088751 Albumins Proteins 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
GUBGYTABKSRVRQ-DCSYEGIMSA-N Beta-Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-DCSYEGIMSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
206010065687 Bone loss Diseases 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
101001018362 Bos taurus Myelin basic protein Proteins 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
102000000844 Cell Surface Receptors Human genes 0.000 description 1
108010001857 Cell Surface Receptors Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 description 1
108020004635 Complementary DNA Proteins 0.000 description 1
108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 description 1
108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 description 1
102100036239 Cyclin-dependent kinase 2 Human genes 0.000 description 1
102100036252 Cyclin-dependent kinase 4 Human genes 0.000 description 1
102000003903 Cyclin-dependent kinases Human genes 0.000 description 1
108090000266 Cyclin-dependent kinases Proteins 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
241000275449 Diplectrum formosum Species 0.000 description 1
101100224482 Drosophila melanogaster PolE1 gene Proteins 0.000 description 1
241000792859 Enema Species 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
241000237858 Gastropoda Species 0.000 description 1
241000206672 Gelidium Species 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
108010024636 Glutathione Proteins 0.000 description 1
208000031886 HIV Infections Diseases 0.000 description 1
208000037357 HIV infectious disease Diseases 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
206010061598 Immunodeficiency Diseases 0.000 description 1
208000029462 Immunodeficiency disease Diseases 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
206010025323 Lymphomas Diseases 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
229920000715 Mucilage Polymers 0.000 description 1
102000047918 Myelin Basic Human genes 0.000 description 1
101710107068 Myelin basic protein Proteins 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
229910003204 NH2 Inorganic materials 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
229910004874 Na2S 9H2O Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
108091034117 Oligonucleotide Proteins 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
208000030852 Parasitic disease Diseases 0.000 description 1
102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 1
108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 1
108091000080 Phosphotransferase Proteins 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
208000008601 Polycythemia Diseases 0.000 description 1
229920001710 Polyorthoester Polymers 0.000 description 1
229920001213 Polysorbate 20 Polymers 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
230000018199 S phase Effects 0.000 description 1
206010040070 Septic Shock Diseases 0.000 description 1
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229920002253 Tannate Polymers 0.000 description 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
239000004473 Threonine Substances 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
229920004890 Triton X-100 Polymers 0.000 description 1
239000013504 Triton X-100 Substances 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 1
SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 1
230000001594 aberrant effect Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
TTWYZDPBDWHJOR-IDIVVRGQSA-L adenosine triphosphate disodium Chemical compound [Na+].[Na+].C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O TTWYZDPBDWHJOR-IDIVVRGQSA-L 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000000539 amino acid group Chemical group 0.000 description 1
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
229960001040 ammonium chloride Drugs 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
230000000692 anti-sense effect Effects 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
239000008122 artificial sweetener Substances 0.000 description 1
235000021311 artificial sweeteners Nutrition 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000011324 bead Substances 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
235000012216 bentonite Nutrition 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
210000002960 bfu-e Anatomy 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
238000010170 biological method Methods 0.000 description 1
229920001400 block copolymer Polymers 0.000 description 1
238000007664 blowing Methods 0.000 description 1
210000001185 bone marrow Anatomy 0.000 description 1
210000002798 bone marrow cell Anatomy 0.000 description 1
239000012267 brine Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
229940105329 carboxymethylcellulose Drugs 0.000 description 1
230000022131 cell cycle Effects 0.000 description 1
230000025084 cell cycle arrest Effects 0.000 description 1
230000012820 cell cycle checkpoint Effects 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
238000000451 chemical ionisation Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229940090805 clavulanate Drugs 0.000 description 1
HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 description 1
230000005757 colony formation Effects 0.000 description 1
230000001332 colony forming effect Effects 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
ACYGYJFTZSAZKR-UHFFFAOYSA-J dicalcium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Ca+2].[Ca+2].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O ACYGYJFTZSAZKR-UHFFFAOYSA-J 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
239000001177 diphosphate Substances 0.000 description 1
XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
235000011180 diphosphates Nutrition 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 1
POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000009510 drug design Methods 0.000 description 1
238000007876 drug discovery Methods 0.000 description 1
229940009662 edetate Drugs 0.000 description 1
229960001484 edetic acid Drugs 0.000 description 1
239000012636 effector Substances 0.000 description 1
229950005627 embonate Drugs 0.000 description 1
239000007920 enema Substances 0.000 description 1
229940079360 enema for constipation Drugs 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
210000002615 epidermis Anatomy 0.000 description 1
210000003743 erythrocyte Anatomy 0.000 description 1
230000010437 erythropoiesis Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
229950000206 estolate Drugs 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
238000010265 fast atom bombardment Methods 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000010419 fine particle Substances 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
239000012530 fluid Substances 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
229940050411 fumarate Drugs 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
102000034356 gene-regulatory proteins Human genes 0.000 description 1
108091006104 gene-regulatory proteins Proteins 0.000 description 1
229960001731 gluceptate Drugs 0.000 description 1
KWMLJOLKUYYJFJ-VFUOTHLCSA-N glucoheptonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O KWMLJOLKUYYJFJ-VFUOTHLCSA-N 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
239000008103 glucose Substances 0.000 description 1
229930195712 glutamate Natural products 0.000 description 1
229940049906 glutamate Drugs 0.000 description 1
229960003180 glutathione Drugs 0.000 description 1
239000003102 growth factor Substances 0.000 description 1
239000000122 growth hormone Substances 0.000 description 1
235000015220 hamburgers Nutrition 0.000 description 1
230000035876 healing Effects 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
239000000017 hydrogel Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
239000008309 hydrophilic cream Substances 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
150000002466 imines Chemical group 0.000 description 1
230000007813 immunodeficiency Effects 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
238000000021 kinase assay Methods 0.000 description 1
229940001447 lactate Drugs 0.000 description 1
229940099584 lactobionate Drugs 0.000 description 1
JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 description 1
229940070765 laurate Drugs 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
239000003446 ligand Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
229940049920 malate Drugs 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000012528 membrane Substances 0.000 description 1
239000001525 mentha piperita l. herb oil Substances 0.000 description 1
LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
LRMHVVPPGGOAJQ-UHFFFAOYSA-N methyl nitrate Chemical compound CO[N+]([O-])=O LRMHVVPPGGOAJQ-UHFFFAOYSA-N 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
239000002324 mouth wash Substances 0.000 description 1
210000003643 myeloid progenitor cell Anatomy 0.000 description 1
DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
BXGTVNLGPMZLAZ-UHFFFAOYSA-N n'-ethylmethanediimine;hydrochloride Chemical compound Cl.CCN=C=N BXGTVNLGPMZLAZ-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000007923 nasal drop Substances 0.000 description 1
229940100662 nasal drops Drugs 0.000 description 1
229940097496 nasal spray Drugs 0.000 description 1
239000007922 nasal spray Substances 0.000 description 1
235000021096 natural sweeteners Nutrition 0.000 description 1
208000004235 neutropenia Diseases 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([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 description 1
229940014662 pantothenate Drugs 0.000 description 1
235000019161 pantothenic acid Nutrition 0.000 description 1
239000011713 pantothenic acid Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000011236 particulate material Substances 0.000 description 1
235000010603 pastilles Nutrition 0.000 description 1
230000007170 pathology Effects 0.000 description 1
235000019477 peppermint oil Nutrition 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
238000003566 phosphorylation assay Methods 0.000 description 1
102000020233 phosphotransferase Human genes 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
229920000747 poly(lactic acid) Polymers 0.000 description 1
229920002721 polycyanoacrylate Polymers 0.000 description 1
239000004626 polylactic acid Substances 0.000 description 1
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
229920006324 polyoxymethylene Polymers 0.000 description 1
229920001184 polypeptide Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
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
230000002335 preservative effect Effects 0.000 description 1
238000003825 pressing Methods 0.000 description 1
208000037920 primary disease Diseases 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
239000011253 protective coating Substances 0.000 description 1
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
102000005962 receptors Human genes 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
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
229940081974 saccharin Drugs 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000002821 scintillation proximity assay Methods 0.000 description 1
238000007789 sealing Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
230000036303 septic shock Effects 0.000 description 1
239000004208 shellac Substances 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
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
210000003491 skin Anatomy 0.000 description 1
238000009491 slugging Methods 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
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
210000000130 stem cell Anatomy 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
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
238000001356 surgical procedure Methods 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
229950002757 teoclate Drugs 0.000 description 1
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
229940124597 therapeutic agent Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
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
241000701447 unidentified baculovirus Species 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003643 water by type Substances 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
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)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Hematology (AREA)
Diabetes (AREA)
Physical Education & Sports Medicine (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

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

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US42838402P	2002-11-22	2002-11-22

Publications (1)

Publication Number	Publication Date
OA12963A true OA12963A (en)	2006-10-13

Family

ID=32393394

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200500154A OA12963A (en)	2002-11-22	2003-11-18	Novel chemical compounds.

Country Status (30)

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

Families Citing this family (36)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES2251677T3 (es)	2002-01-22	2006-05-01	Warner-Lambert Company Llc	2-(piridin-2-ilamino)-pirido(2,3-d)pirimidin-7-onas.
ATE412650T1 (de) *	2003-07-11	2008-11-15	Warner Lambert Co	Isethionat salz eines selektiven cdk4 inhibitors
DE602004022170D1 (de) *	2003-07-28	2009-09-03	Merck Serono Sa Coinsins	2-imino-4-(thio)oxo-5-polycyclovinylazoline zur verwendung als pi3-kinase-inhibtoren
USRE43833E1 (en)	2003-11-21	2012-11-27	Actelion Pharmaceuticals Ltd.	Thiazolidin-4-one derivatives
PT1689726E (pt)	2003-11-21	2010-12-09	Actelion Pharmaceuticals Ltd	Derivados de 5-(benz-(z)-ilideno)-tiazolidin-4-ona como agentes imunossupressores
JP2007523957A (ja) *	2004-02-25	2007-08-23	スミスクライン・ビーチャム・コーポレイション	新規化学化合物
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
MXPA06015026A (es) *	2004-07-01	2007-02-08	Hoffmann La Roche	Nuevas quinolinas de tiazolinonas con actividad antiproliferante de las cinasas dependientes de ciclina 1 (cdk1).
EP1765817A1 (en)	2004-07-01	2007-03-28	F.Hoffmann-La Roche Ag	Thiazolinone unsubstituted quinolines
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
AU2005293556A1 (en) *	2004-10-12	2006-04-20	Merck Serono Sa	PI3 Kinase gamma inhibitors for the treatment of anaemia
PL1805175T3 (pl) *	2004-10-14	2008-08-29	Hoffmann La Roche	Nowe azaindolotiazolinony jako środki przeciwrakowe
MX2007004276A (es) *	2004-10-14	2007-05-16	Hoffmann La Roche	1,5-naftiridin-azolidinonas que tienen actividad antiproliferativa de cdk-1.
RU2405782C2 (ru) *	2004-10-14	2010-12-10	Ф.Хоффманн-Ля Рош Аг	Хиназолинилметилентиазолиноны в качестве cdk-1 ингибиторов
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
JP2008545690A (ja) *	2005-05-23	2008-12-18	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
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
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
TW200745066A (en)	2005-09-16	2007-12-16	Torrent Pharmaceuticals Ltd	Novel PTP1B inhibitors
US20080262027A1 (en) *	2005-11-08	2008-10-23	Duffy Kevin J	Novel Chemical Compounds
US20100216801A1 (en) *	2006-03-02	2010-08-26	Dashyant Dhanak	Thiazolones for use as pi3 kinase inhibitors
EP1993535A4 (en) *	2006-03-02	2011-04-20	Glaxosmithkline Llc	THIAZOLONE AS A PI3 KINASE INHIBITOR
KR100752757B1 (ko) *	2006-04-05	2007-08-29	한국과학기술연구원	2-페닐이미노-1,3-티아졸린을 포함하는 미백 조성물
KR20090007609A (ko) *	2006-04-25	2009-01-19	더 클리브랜드 클리닉 파운데이션	ＲＮａｓｅＬ을 활성화시키는 항-바이러스 제제
US8912340B2 (en)	2006-11-23	2014-12-16	Actelion Pharmaceuticals Ltd.	Process for the preparation of 2-imino-thiazolidin-4-one derivatives
US8263780B2 (en) *	2006-11-23	2012-09-11	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
KR20120024619A (ko)	2009-04-20	2012-03-14	에스비아이 바이오테크 가부시키가이샤	티아졸리디논 유도체
CN104520303B (zh)	2012-07-30	2017-04-12	国立大学法人京都大学	关于精神神经疾病或恶性肿瘤的化合物及医药组合物
MX350891B (es)	2012-08-17	2017-09-22	Actelion Pharmaceuticals Ltd	Proceso para la preparacion de (2z,5z)-5-(3-cloro-4-((r)-2,3-dihid roxipropoxi) bencilideno)-2-(propilimino)-3-(o-tolil) tiazolidin-4-ona y el intermediario usado en dicho proceso.
RU2521390C1 (ru) *	2013-03-14	2014-06-27	Общество с ограниченной ответственностью "Тиацен"	Производное роданина и средство для профилактики опухолевых заболеваний
ES2910455T3 (es) *	2014-05-28	2022-05-12	Univ Bern	Compuestos de tiazolidinona y su uso en el tratamiento de condiciones psiquiátricas o trastornos neurológicos e inflamación, en particular neuroinflamación
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 (no) *	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
JP2539504B2 (ja)	1987-03-11	1996-10-02	鐘淵化学工業株式会社	ヒドロキシスチレン誘導体
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
IL100874A (en) *	1991-02-08	1996-01-19	Pro Neuron Inc	Oxypurine nucleosides and related compounds for use as medicaments their preparation and pharmaceutical compositions containing them
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
DE69318863T2 (de)	1992-02-03	1998-09-24	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
EP0915090A1 (en) *	1992-09-10	1999-05-12	Eli Lilly And Company	Compounds useful as hypoglycemic agents and for treating Alzheimer's disease
EP0587229B1 (en)	1992-09-11	2002-05-08	Agfa-Gevaert	Photographic element containing a filter dye for rapid processing applications
EP0587230B1 (en)	1992-09-11	2003-11-26	Agfa-Gevaert	Photographic element containing a filter dye for rapid processing applications
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
CA2227829A1 (en) *	1995-07-31	1997-02-13	Shionogi & Co., Ltd.	Pyrrolidine derivatives having phospholipase a2 inhibitory activity
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
AU6062900A (en)	1999-07-01	2001-01-22	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 (en)	2000-07-05	2004-11-03	Synaptic Pharma Corp	SELECTIVE RECEPTOR ANTAGONISTS OF MELANINE CONCENTRATING HORMON-1 (MCH1) AND THEIR USE
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
TW200304375A (en) *	2001-12-06	2003-10-01	Maxia Pharmaceuticals Inc	2-Substituted thiazolidinone and oxazolidinone derivatives for the inhibition of phosphatases and the treatment of cancer

2003
- 2003-11-18 MX MXPA05005406A patent/MXPA05005406A/es active IP Right Grant
- 2003-11-18 EP EP03796448A patent/EP1567112B1/en not_active Expired - Lifetime
- 2003-11-18 JP JP2004555721A patent/JP2006509765A/ja not_active Ceased
- 2003-11-18 NZ NZ539873A patent/NZ539873A/en not_active IP Right Cessation
- 2003-11-18 SI SI200331463T patent/SI1567112T1/sl unknown
- 2003-11-18 US US10/535,690 patent/US7767701B2/en not_active Expired - Fee Related
- 2003-11-18 PL PL377564A patent/PL377564A1/pl not_active Application Discontinuation
- 2003-11-18 UA UAA200504788A patent/UA80572C2/uk unknown
- 2003-11-18 DE DE60324178T patent/DE60324178D1/de not_active Expired - Lifetime
- 2003-11-18 CN CN200380109119A patent/CN100579978C/zh not_active Expired - Fee Related
- 2003-11-18 DK DK03796448T patent/DK1567112T3/da active
- 2003-11-18 PT PT03796448T patent/PT1567112E/pt unknown
- 2003-11-18 ES ES03796448T patent/ES2315566T3/es not_active Expired - Lifetime
- 2003-11-18 KR KR1020057009243A patent/KR20050085115A/ko not_active Ceased
- 2003-11-18 AT AT03796448T patent/ATE411302T1/de active
- 2003-11-18 OA OA1200500154A patent/OA12963A/en unknown
- 2003-11-18 EA EA200500856A patent/EA008865B1/ru not_active IP Right Cessation
- 2003-11-18 BR BR0316502-7A patent/BR0316502A/pt not_active IP Right Cessation
- 2003-11-18 WO PCT/US2003/037658 patent/WO2004047760A2/en not_active Ceased
- 2003-11-18 CA CA002507256A patent/CA2507256A1/en not_active Abandoned
- 2003-11-18 AP AP2005003304A patent/AP1967A/xx active
- 2003-11-18 AU AU2003298693A patent/AU2003298693B2/en not_active Ceased
- 2003-11-20 TW TW092132476A patent/TWI309648B/zh not_active IP Right Cessation
- 2003-11-20 AR ARP030104299A patent/AR045407A1/es not_active Application Discontinuation
- 2003-11-20 MY MYPI20034473A patent/MY140132A/en unknown
2005
- 2005-05-20 EC EC2005005808A patent/ECSP055808A/es unknown
- 2005-05-27 MA MA28303A patent/MA27701A1/fr unknown
- 2005-06-02 IS IS7879A patent/IS2659B/is unknown
- 2005-06-15 NO NO20052928A patent/NO20052928L/no not_active Application Discontinuation
2008
- 2008-12-29 CY CY20081101499T patent/CY1108655T1/el unknown

Also Published As

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

Publication	Publication Date	Title
EP1567112B1 (en)	2008-10-15	THIAZOLIDIN-4-ONES FOR INHIBITING hYAK3 PROTEINS
CN107207479B (zh)	2020-11-20	作为磷脂酰肌醇3-激酶δ抑制剂的取代嘧啶类化合物及其应用
EP2590950A1 (en)	2013-05-15	N-cyclyl-3 - (cyclylcarbonylaminomethyl) benzamide derivatives as rho kinase inhibitors
PT1689726E (pt)	2010-12-09	Derivados de 5-(benz-(z)-ilideno)-tiazolidin-4-ona como agentes imunossupressores
JP2021529746A (ja)	2021-11-04	心臓サルコメア阻害剤
WO2009010871A2 (en)	2009-01-22	Pyrazole derivatives as antagonists of adenosine a3 receptor
JP2016505040A (ja)	2016-02-18	アルドース還元酵素阻害剤およびその使用
CN108779110A (zh)	2018-11-09	磷脂酰肌醇3-激酶γ的新颖抑制剂
US20070249599A1 (en)	2007-10-25	Novel Chemical Compounds
WO2012054367A1 (en)	2012-04-26	Rho kinase inhibitors
US20080214455A1 (en)	2008-09-04	Novel Chemical Compounds
US20060178384A1 (en)	2006-08-10	Novel chemical compounds
JP2007517886A (ja)	2007-07-05	新規な化学化合物
US7550598B2 (en)	2009-06-23	Kinase inhibitors
WO2005068458A2 (en)	2005-07-28	Five-membered heterocyclic compounds as inhibitors of src family protein kinase
US20090203692A1 (en)	2009-08-13	Novel chemical compounds
US20080261974A1 (en)	2008-10-23	Novel Chemical Compounds
JP2006519234A (ja)	2006-08-24	新規化合物
HK1083443B (en)	2009-07-10	Thiazolidin-4-ones for inhibiting hyak3 proteins
EP4422753A1 (en)	2024-09-04	Imidazolone derivatives as inhibitors of protein kinases in particular dyrk1a, clk1 and/or clk4
JP2009514984A (ja)	2009-04-09	新規化合物