CA2704711C - Thiazolopyrimidine p13k inhibitor compounds and methods of use - Google Patents
Thiazolopyrimidine p13k inhibitor compounds and methods of use Download PDFInfo
- Publication number
- CA2704711C CA2704711C CA2704711A CA2704711A CA2704711C CA 2704711 C CA2704711 C CA 2704711C CA 2704711 A CA2704711 A CA 2704711A CA 2704711 A CA2704711 A CA 2704711A CA 2704711 C CA2704711 C CA 2704711C
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- CA
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- Prior art keywords
- pyrimidin
- compound
- morpholinothiazolo
- amine
- group
- Prior art date
- Legal status (The legal status 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 status listed.)
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 261
- 238000000034 method Methods 0.000 title claims abstract description 139
- 239000003112 inhibitor Substances 0.000 title description 13
- 150000008634 thiazolopyrimidines Chemical class 0.000 title description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 47
- 150000003839 salts Chemical class 0.000 claims abstract description 38
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 37
- 238000011282 treatment Methods 0.000 claims abstract description 33
- 201000011510 cancer Diseases 0.000 claims abstract description 28
- 108091007960 PI3Ks Proteins 0.000 claims abstract description 20
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 9
- 230000001404 mediated effect Effects 0.000 claims abstract 2
- -1 C3-C12 carbocyclyl Chemical group 0.000 claims description 119
- 125000000623 heterocyclic group Chemical group 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 125000001072 heteroaryl group Chemical group 0.000 claims description 43
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 43
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 125000002619 bicyclic group Chemical group 0.000 claims description 28
- 208000035475 disorder Diseases 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 23
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 23
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 23
- 229910052794 bromium Inorganic materials 0.000 claims description 21
- 125000000304 alkynyl group Chemical group 0.000 claims description 19
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 18
- 230000000694 effects Effects 0.000 claims description 17
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 16
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 16
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 14
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
- 239000003085 diluting agent Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
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- 125000004193 piperazinyl group Chemical group 0.000 claims description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 8
- 125000002757 morpholinyl group Chemical group 0.000 claims description 8
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- 125000003386 piperidinyl group Chemical group 0.000 claims description 8
- 125000006413 ring segment Chemical group 0.000 claims description 8
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
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- 125000002950 monocyclic group Chemical group 0.000 claims description 6
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- 125000001041 indolyl group Chemical group 0.000 claims description 5
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
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- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- MZFFDQURQNGOPA-UHFFFAOYSA-N 5-(7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-yl)pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(N=CS2)C2=N1 MZFFDQURQNGOPA-UHFFFAOYSA-N 0.000 claims description 3
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims description 3
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- 206010001233 Adenoma benign Diseases 0.000 claims description 3
- 208000010667 Carcinoma of liver and intrahepatic biliary tract Diseases 0.000 claims description 3
- 206010073069 Hepatic cancer Diseases 0.000 claims description 3
- 208000017604 Hodgkin disease Diseases 0.000 claims description 3
- 206010023347 Keratoacanthoma Diseases 0.000 claims description 3
- 206010025323 Lymphomas Diseases 0.000 claims description 3
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- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
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- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
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- 210000000813 small intestine Anatomy 0.000 claims description 3
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- 210000001550 testis Anatomy 0.000 claims description 3
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- 210000002105 tongue Anatomy 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- 208000010576 undifferentiated carcinoma Diseases 0.000 claims description 3
- 208000010570 urinary bladder carcinoma Diseases 0.000 claims description 3
- ZIOBGZDFMKCKGZ-UHFFFAOYSA-N 2-amino-2-methylpropanamide Chemical compound CC(C)(N)C(N)=O ZIOBGZDFMKCKGZ-UHFFFAOYSA-N 0.000 claims description 2
- DRYMMXUBDRJPDS-UHFFFAOYSA-N 2-hydroxy-2-methylpropanamide Chemical group CC(C)(O)C(N)=O DRYMMXUBDRJPDS-UHFFFAOYSA-N 0.000 claims description 2
- TZGPACAKMCUCKX-UHFFFAOYSA-N 2-hydroxyacetamide Chemical compound NC(=O)CO TZGPACAKMCUCKX-UHFFFAOYSA-N 0.000 claims description 2
- MTEZLAATISORQK-UHFFFAOYSA-N 2-methoxyacetamide Chemical group COCC(N)=O MTEZLAATISORQK-UHFFFAOYSA-N 0.000 claims description 2
- DARMXCIKWOEHNQ-UHFFFAOYSA-N 5-[7-morpholin-4-yl-2-(6-morpholin-4-ylpyridin-3-yl)-[1,3]thiazolo[5,4-d]pyrimidin-5-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(N=C(S2)C=3C=NC(=CC=3)N3CCOCC3)C2=N1 DARMXCIKWOEHNQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- SXQFCVDSOLSHOQ-UHFFFAOYSA-N lactamide Chemical group CC(O)C(N)=O SXQFCVDSOLSHOQ-UHFFFAOYSA-N 0.000 claims description 2
- FABZXXJETVNBBX-UHFFFAOYSA-N n-(hydrazinecarbonyl)acetamide Chemical compound CC(=O)NC(=O)NN FABZXXJETVNBBX-UHFFFAOYSA-N 0.000 claims description 2
- 230000000069 prophylactic effect Effects 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 229910004749 OS(O)2 Inorganic materials 0.000 claims 2
- GHIWCRRQTAWFDI-ZDUSSCGKSA-N (2s)-1-[4-[[5-(2-aminopyrimidin-5-yl)-7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-2-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=NC2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2S1 GHIWCRRQTAWFDI-ZDUSSCGKSA-N 0.000 claims 1
- KMKVSCJQCXIOFU-KRWDZBQOSA-N (2s)-2-hydroxy-1-[4-[(7-morpholin-4-yl-5-quinolin-3-yl-[1,3]thiazolo[5,4-d]pyrimidin-2-yl)methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=NC2=C(N3CCOCC3)N=C(C=3C=C4C=CC=CC4=NC=3)N=C2S1 KMKVSCJQCXIOFU-KRWDZBQOSA-N 0.000 claims 1
- NAVFVILLJQALAO-AWEZNQCLSA-N (2s)-2-hydroxy-1-[4-[[5-[2-(methylamino)pyrimidin-5-yl]-7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-2-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1=NC(NC)=NC=C1C1=NC(N2CCOCC2)=C(N=C(CN2CCN(CC2)C(=O)[C@H](C)O)S2)C2=N1 NAVFVILLJQALAO-AWEZNQCLSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 claims 1
- HKUALZOSZZIXFL-UHFFFAOYSA-N 2-[4-[5-(2-aminopyrimidin-5-yl)-7-morpholin-4-yl-[1,3]thiazolo[4,5-d]pyrimidin-2-yl]piperazin-1-yl]ethanol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=N2)N3CCN(CCO)CC3)C2=N1 HKUALZOSZZIXFL-UHFFFAOYSA-N 0.000 claims 1
- WQXWWQQZDJXVNO-UHFFFAOYSA-N 2-[5-(2-aminopyrimidin-5-yl)-7-morpholin-4-yl-[1,3]thiazolo[4,5-d]pyrimidin-2-yl]propan-2-ol Chemical compound C=12SC(C(C)(O)C)=NC2=NC(C=2C=NC(N)=NC=2)=NC=1N1CCOCC1 WQXWWQQZDJXVNO-UHFFFAOYSA-N 0.000 claims 1
- BKVQEYGHPGUWQD-UHFFFAOYSA-N 2-[5-(2-aminopyrimidin-5-yl)-7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-2-yl]propan-2-ol Chemical compound N1=C2SC(C(C)(O)C)=NC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 BKVQEYGHPGUWQD-UHFFFAOYSA-N 0.000 claims 1
- WBJWLCXGPNDRNE-UHFFFAOYSA-N 4-[2-(3-methylsulfonylphenyl)-5-(1h-pyrrolo[2,3-b]pyridin-5-yl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]morpholine Chemical compound CS(=O)(=O)C1=CC=CC(C=2SC3=NC(=NC(=C3N=2)N2CCOCC2)C=2C=C3C=CNC3=NC=2)=C1 WBJWLCXGPNDRNE-UHFFFAOYSA-N 0.000 claims 1
- ZWRGXXOESNIQAX-UHFFFAOYSA-N 4-[2-[(4-methylsulfonylpiperazin-1-yl)methyl]-5-quinolin-3-yl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=NC2=C(N3CCOCC3)N=C(C=3C=C4C=CC=CC4=NC=3)N=C2S1 ZWRGXXOESNIQAX-UHFFFAOYSA-N 0.000 claims 1
- XWMPLWQFKDVMEW-UHFFFAOYSA-N 4-[5-(1h-indazol-4-yl)-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=NC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 XWMPLWQFKDVMEW-UHFFFAOYSA-N 0.000 claims 1
- YYVPTELQQDKFEH-UHFFFAOYSA-N 4-[5-(1h-indazol-4-yl)-2-methylsulfanyl-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]morpholine Chemical compound C=12SC(SC)=NC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1N1CCOCC1 YYVPTELQQDKFEH-UHFFFAOYSA-N 0.000 claims 1
- AIZJZJLEDOHHKD-UHFFFAOYSA-N 5-(2,7-dimorpholin-4-yl-[1,3]thiazolo[4,5-d]pyrimidin-5-yl)pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=N2)N3CCOCC3)C2=N1 AIZJZJLEDOHHKD-UHFFFAOYSA-N 0.000 claims 1
- UMSVIVMHIYAPKM-UHFFFAOYSA-N 5-(2-aminopyrimidin-5-yl)-7-morpholin-4-yl-n-(2-morpholin-4-ylethyl)-[1,3]thiazolo[4,5-d]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(NCCN2CCOCC2)=N2)C2=N1 UMSVIVMHIYAPKM-UHFFFAOYSA-N 0.000 claims 1
- YQLKXXRYRSSZRK-UHFFFAOYSA-N 5-(2-aminopyrimidin-5-yl)-7-morpholin-4-yl-n-(4-morpholin-4-ylphenyl)-[1,3]thiazolo[5,4-d]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(N=C(NC=2C=CC(=CC=2)N2CCOCC2)S2)C2=N1 YQLKXXRYRSSZRK-UHFFFAOYSA-N 0.000 claims 1
- CGYKLGPAIOWHQT-UHFFFAOYSA-N 5-(2-aminopyrimidin-5-yl)-7-morpholin-4-yl-n-phenyl-[1,3]thiazolo[5,4-d]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(N=C(NC=2C=CC=CC=2)S2)C2=N1 CGYKLGPAIOWHQT-UHFFFAOYSA-N 0.000 claims 1
- WHLWCBZDOTZYRU-UHFFFAOYSA-N 5-(2-aminopyrimidin-5-yl)-n-(2-methylsulfonylethyl)-7-morpholin-4-yl-[1,3]thiazolo[4,5-d]pyrimidin-2-amine Chemical compound C=12SC(NCCS(=O)(=O)C)=NC2=NC(C=2C=NC(N)=NC=2)=NC=1N1CCOCC1 WHLWCBZDOTZYRU-UHFFFAOYSA-N 0.000 claims 1
- SXCBYWYHMBCUDQ-UHFFFAOYSA-N 5-(2-aminopyrimidin-5-yl)-n-(4-methylsulfonylphenyl)-7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC1=NC2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2S1 SXCBYWYHMBCUDQ-UHFFFAOYSA-N 0.000 claims 1
- WQSMDTDOYOBTOL-UHFFFAOYSA-N 5-(6-aminopyridin-3-yl)-7-morpholin-4-yl-n-phenyl-[1,3]thiazolo[4,5-d]pyrimidin-2-amine Chemical compound C1=NC(N)=CC=C1C1=NC(N2CCOCC2)=C(SC(NC=2C=CC=CC=2)=N2)C2=N1 WQSMDTDOYOBTOL-UHFFFAOYSA-N 0.000 claims 1
- AUQJUYJSLJLZJN-UHFFFAOYSA-N 5-(6-aminopyridin-3-yl)-n-methyl-n-(1-methylpiperidin-4-yl)-7-morpholin-4-yl-[1,3]thiazolo[4,5-d]pyrimidin-2-amine Chemical compound N=1C2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2SC=1N(C)C1CCN(C)CC1 AUQJUYJSLJLZJN-UHFFFAOYSA-N 0.000 claims 1
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- VDRORYMZHVKZHC-UHFFFAOYSA-N 5-[2-(3-methylsulfonylphenyl)-7-morpholin-4-yl-[1,3]thiazolo[4,5-d]pyrimidin-5-yl]pyrimidin-2-amine Chemical compound CS(=O)(=O)C1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3N=2)C=2C=NC(N)=NC=2)=C1 VDRORYMZHVKZHC-UHFFFAOYSA-N 0.000 claims 1
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- WPJUQICNCRUAIN-UHFFFAOYSA-N 5-[2-(4-methoxypyridin-3-yl)-7-morpholin-4-yl-[1,3]thiazolo[4,5-d]pyrimidin-5-yl]pyridin-2-amine Chemical compound COC1=CC=NC=C1C1=NC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 WPJUQICNCRUAIN-UHFFFAOYSA-N 0.000 claims 1
- BSSCCGPVFYKTDF-UHFFFAOYSA-N 5-[2-(4-methoxypyridin-3-yl)-7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-yl]pyrimidin-2-amine Chemical compound COC1=CC=NC=C1C1=NC2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2S1 BSSCCGPVFYKTDF-UHFFFAOYSA-N 0.000 claims 1
- DTLARHYDABOITR-UHFFFAOYSA-N 5-[2-(4-methylsulfonylpiperazin-1-yl)-7-morpholin-4-yl-[1,3]thiazolo[4,5-d]pyrimidin-5-yl]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1C1=NC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 DTLARHYDABOITR-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| US60/974,708 | 2007-09-24 | ||
| PCT/US2008/077394 WO2009042607A1 (en) | 2007-09-24 | 2008-09-23 | Thiazolopyrimidine p13k inhibitor compounds and methods of use |
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| CA2704711A1 CA2704711A1 (en) | 2009-04-02 |
| CA2704711C true CA2704711C (en) | 2016-07-05 |
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| ES (1) | ES2399774T3 (OSRAM) |
| WO (1) | WO2009042607A1 (OSRAM) |
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| US7754208B2 (en) | 2001-01-17 | 2010-07-13 | Trubion Pharmaceuticals, Inc. | Binding domain-immunoglobulin fusion proteins |
| HUE026303T2 (hu) | 2005-07-25 | 2016-06-28 | Emergent Product Dev Seattle | B-sejt csökkentés CD37-specifikus és CD20-specifikus kapcsoló molekulák alkalmazásával |
| CN105837690A (zh) | 2006-06-12 | 2016-08-10 | 新兴产品开发西雅图有限公司 | 具有效应功能的单链多价结合蛋白 |
| JP5539190B2 (ja) * | 2007-06-12 | 2014-07-02 | エフ．ホフマン−ラ ロシュ アーゲー | チアゾロピリミジン類及びホスファチジルイノシトール−３キナーゼのインヒビターとしてのそれらの使用 |
| ES2399774T3 (es) * | 2007-09-24 | 2013-04-03 | Genentech, Inc. | Compuestos de tiazolopirimidina inhibidores de PI3K y métodos de uso |
| GB0721095D0 (en) * | 2007-10-26 | 2007-12-05 | Piramed Ltd | Pharmaceutical compounds |
| US9029411B2 (en) | 2008-01-25 | 2015-05-12 | Millennium Pharmaceuticals, Inc. | Thiophenes and uses thereof |
| AU2009234277B2 (en) | 2008-04-11 | 2014-12-04 | Aptevo Research And Development Llc | CD37 immunotherapeutic and combination with bifunctional chemotherapeutic thereof |
| CN102066365A (zh) * | 2008-06-19 | 2011-05-18 | 米伦纽姆医药公司 | 噻吩或噻唑衍生物和其作为pi3k抑制剂的用途 |
| KR20110046514A (ko) * | 2008-07-31 | 2011-05-04 | 제넨테크, 인크. | 피리미딘 화합물, 조성물 및 사용 방법 |
| TWI378933B (en) | 2008-10-14 | 2012-12-11 | Daiichi Sankyo Co Ltd | Morpholinopurine derivatives |
| US9090601B2 (en) | 2009-01-30 | 2015-07-28 | Millennium Pharmaceuticals, Inc. | Thiazole derivatives |
| US9139589B2 (en) | 2009-01-30 | 2015-09-22 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| US8796314B2 (en) | 2009-01-30 | 2014-08-05 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| CA2754890C (en) * | 2009-03-13 | 2018-01-16 | Piet Herdewijn | Bicyclic heterocycles |
| MY160454A (en) | 2009-04-30 | 2017-03-15 | Glaxo Group Ltd | Oxazole substituted indazoles as pi3-kinase inhibitors |
| US8410095B2 (en) * | 2009-05-20 | 2013-04-02 | Glaxosmithkline Llc | Thiazolopyrimidinone derivatives as PI3 kinase inhibitors |
| WO2010135493A2 (en) * | 2009-05-20 | 2010-11-25 | Emory University | Alzheimer's disease imaging agents |
| EP2451811A1 (en) * | 2009-05-27 | 2012-05-16 | F. Hoffmann-La Roche AG | Bicyclic indole-pyrimidine pi3k inhibitor compounds selective for p110 delta, and methods of use |
| CA2761445A1 (en) * | 2009-05-27 | 2010-12-02 | Genentech, Inc. | Bicyclic pyrimidine pi3k inhibitor compounds selective for p110 delta, and methods of use |
| CN102480961A (zh) * | 2009-06-24 | 2012-05-30 | 健泰科生物技术公司 | 与含氧杂环稠合的嘧啶化合物、组合物和使用方法 |
| MX2012005463A (es) * | 2009-11-12 | 2012-09-12 | Hoffmann La Roche | Compuestos de purina n/9 sustituida, composiciones y metodos de uso. |
| BR112012011147A2 (pt) * | 2009-11-12 | 2021-09-08 | F.Hoffmann-La Roche Ag | Composto, composição farmacêutica e uso de um composto. |
| AR079814A1 (es) | 2009-12-31 | 2012-02-22 | Otsuka Pharma Co Ltd | Compuestos heterociclicos, composiciones farmaceuticas que los contienen y sus usos |
| EP3399026B1 (en) | 2010-06-14 | 2024-06-26 | The Scripps Research Institute | Reprogramming of cells to a new fate |
| CN103003279B (zh) | 2010-07-14 | 2015-09-23 | 弗·哈夫曼-拉罗切有限公司 | 对PI3K P110δ具有选择性的嘌呤化合物及其使用方法 |
| MA34797B1 (fr) | 2010-08-11 | 2014-01-02 | Millennium Pharm Inc | Hétéroaryles et leurs utilisations |
| US9062038B2 (en) | 2010-08-11 | 2015-06-23 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| JP2013533318A (ja) | 2010-08-11 | 2013-08-22 | ミレニアム ファーマシューティカルズ， インコーポレイテッド | ヘテロアリールおよびその使用 |
| JP5822934B2 (ja) | 2010-09-15 | 2015-11-25 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | アザベンゾチアゾール化合物、組成物及び使用方法 |
| PH12013500723A1 (en) | 2010-10-13 | 2017-08-23 | Millennium Pharm Inc | Heteroaryls and uses thereof |
| CA2817785A1 (en) | 2010-11-19 | 2012-05-24 | Toby Blench | Pyrazolopyridines and pyrazolopyridines and their use as tyk2 inhibitors |
| EP3053925A1 (en) | 2010-12-16 | 2016-08-10 | F. Hoffmann-La Roche AG | Tricyclic pi3k inhibitor compounds and methods of use |
| AU2012267556B9 (en) | 2011-06-09 | 2017-05-11 | Rhizen Pharmaceuticals Sa | Novel compounds as modulators of GPR-119 |
| JP6121658B2 (ja) * | 2011-06-29 | 2017-04-26 | 大塚製薬株式会社 | 治療用化合物、及び関連する使用の方法 |
| KR20160027218A (ko) | 2012-05-23 | 2016-03-09 | 에프. 호프만-라 로슈 아게 | 내배엽 및 간세포를 수득하고 사용하는 조성물 및 방법 |
| TW201410657A (zh) | 2012-08-02 | 2014-03-16 | Endo Pharmaceuticals Inc | 經取代胺基－嘧啶衍生物 |
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| CN104557872B (zh) * | 2013-10-16 | 2017-05-24 | 上海璎黎药业有限公司 | 稠合杂环化合物、其制备方法、药物组合物和用途 |
| WO2017053469A2 (en) | 2015-09-21 | 2017-03-30 | Aptevo Research And Development Llc | Cd3 binding polypeptides |
| TW201813963A (zh) | 2016-09-23 | 2018-04-16 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| TW201825465A (zh) | 2016-09-23 | 2018-07-16 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| TW201815787A (zh) | 2016-09-23 | 2018-05-01 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
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| US3773919A (en) | 1969-10-23 | 1973-11-20 | Du Pont | Polylactide-drug mixtures |
| BE759493A (fr) | 1969-11-26 | 1971-05-25 | Thomae Gmbh Dr K | Nouvelles 2-(5-nitro-2-furyl)-thieno(3,2-d) pyrimidines et procedes pour les fabriquer |
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- 2008-09-23 EP EP08832932A patent/EP2207781B1/en active Active
- 2008-09-23 US US12/236,317 patent/US7893059B2/en active Active
- 2008-09-23 JP JP2010526059A patent/JP5736171B2/ja active Active
- 2008-09-23 CA CA2704711A patent/CA2704711C/en not_active Expired - Fee Related
- 2008-09-23 CN CN2008801184715A patent/CN101932587A/zh active Pending
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Also Published As
| Publication number | Publication date |
|---|---|
| ES2399774T3 (es) | 2013-04-03 |
| JP2010540458A (ja) | 2010-12-24 |
| US8158626B2 (en) | 2012-04-17 |
| WO2009042607A1 (en) | 2009-04-02 |
| US20110112085A1 (en) | 2011-05-12 |
| CN101932587A (zh) | 2010-12-29 |
| EP2207781A1 (en) | 2010-07-21 |
| US20090118275A1 (en) | 2009-05-07 |
| US7893059B2 (en) | 2011-02-22 |
| JP5736171B2 (ja) | 2015-06-17 |
| CA2704711A1 (en) | 2009-04-02 |
| EP2207781B1 (en) | 2012-11-28 |
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