JP2013541536A5 - - Google Patents
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- JP2013541536A5 JP2013541536A5 JP2013531796A JP2013531796A JP2013541536A5 JP 2013541536 A5 JP2013541536 A5 JP 2013541536A5 JP 2013531796 A JP2013531796 A JP 2013531796A JP 2013531796 A JP2013531796 A JP 2013531796A JP 2013541536 A5 JP2013541536 A5 JP 2013541536A5
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- JP
- Japan
- Prior art keywords
- substituted
- compound
- unsubstituted
- formula
- hydrogen
- 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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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 49
- 239000002904 solvent Substances 0.000 claims description 47
- 239000012453 solvate Substances 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 150000002367 halogens Chemical class 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 31
- 229940126062 Compound A Drugs 0.000 claims description 29
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 29
- 239000002585 base Substances 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 238000002441 X-ray diffraction Methods 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- -1 monohydrochloride compound Chemical class 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical class [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 125000002015 acyclic group Chemical group 0.000 claims description 6
- 238000005755 formation reaction Methods 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 229940124530 sulfonamide Drugs 0.000 claims description 5
- 150000003456 sulfonamides Chemical class 0.000 claims description 5
- 206010009944 Colon cancer Diseases 0.000 claims description 4
- 208000008770 Multiple Hamartoma Syndrome Diseases 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000003849 aromatic solvent Substances 0.000 claims description 4
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 239000003759 ester based solvent Substances 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 claims description 4
- 150000004682 monohydrates Chemical class 0.000 claims description 4
- 230000009826 neoplastic cell growth Effects 0.000 claims description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 4
- 239000003880 polar aprotic solvent Substances 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 claims description 3
- PBIMIGNDTBRRPI-UHFFFAOYSA-N trifluoro borate Chemical compound FOB(OF)OF PBIMIGNDTBRRPI-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 claims description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 201000007815 Bannayan-Riley-Ruvalcaba syndrome Diseases 0.000 claims description 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 2
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 208000012609 Cowden disease Diseases 0.000 claims description 2
- 201000002847 Cowden syndrome Diseases 0.000 claims description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
- 206010061968 Gastric neoplasm Diseases 0.000 claims description 2
- 206010017993 Gastrointestinal neoplasms Diseases 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- 206010025323 Lymphomas Diseases 0.000 claims description 2
- 208000034578 Multiple myelomas Diseases 0.000 claims description 2
- 206010033128 Ovarian cancer Diseases 0.000 claims description 2
- 108091007960 PI3Ks Proteins 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 206010039491 Sarcoma Diseases 0.000 claims description 2
- 208000033781 Thyroid carcinoma Diseases 0.000 claims description 2
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 2
- 201000003761 Vaginal carcinoma Diseases 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 210000004100 adrenal gland Anatomy 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 210000004556 brain Anatomy 0.000 claims description 2
- 210000000481 breast Anatomy 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 210000001072 colon Anatomy 0.000 claims description 2
- 208000029742 colonic neoplasm Diseases 0.000 claims description 2
- 201000002758 colorectal adenoma Diseases 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 208000021045 exocrine pancreatic carcinoma Diseases 0.000 claims description 2
- 208000005017 glioblastoma Diseases 0.000 claims description 2
- 150000004795 grignard reagents Chemical class 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims description 2
- 210000003734 kidney Anatomy 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 210000004185 liver Anatomy 0.000 claims description 2
- 210000004072 lung Anatomy 0.000 claims description 2
- 201000005296 lung carcinoma Diseases 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 210000001672 ovary Anatomy 0.000 claims description 2
- 210000000496 pancreas Anatomy 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 230000037361 pathway Effects 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 230000002062 proliferating effect Effects 0.000 claims description 2
- 210000002307 prostate Anatomy 0.000 claims description 2
- 201000001514 prostate carcinoma Diseases 0.000 claims description 2
- 201000004240 prostatic hypertrophy Diseases 0.000 claims description 2
- 208000020615 rectal carcinoma Diseases 0.000 claims description 2
- 210000000664 rectum Anatomy 0.000 claims description 2
- 210000002784 stomach Anatomy 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 201000002510 thyroid cancer Diseases 0.000 claims description 2
- 208000013077 thyroid gland carcinoma Diseases 0.000 claims description 2
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical group CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 claims description 2
- 210000003932 urinary bladder Anatomy 0.000 claims description 2
- 210000001215 vagina Anatomy 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims 4
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- 230000036571 hydration Effects 0.000 claims 1
- 238000006703 hydration reaction Methods 0.000 claims 1
- 0 CC*C1NC(N2CCOCC2)=NC(C)=C1* Chemical compound CC*C1NC(N2CCOCC2)=NC(C)=C1* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38872110P | 2010-10-01 | 2010-10-01 | |
| US61/388,721 | 2010-10-01 | ||
| US201161494915P | 2011-06-09 | 2011-06-09 | |
| US61/494,915 | 2011-06-09 | ||
| PCT/US2011/053808 WO2012044727A2 (en) | 2010-10-01 | 2011-09-29 | Manufacturing process for pyrimidine derivatives |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015246502A Division JP2016106091A (ja) | 2010-10-01 | 2015-12-17 | ピリミジン誘導体の製造プロセス |
| JP2015246501A Division JP2016128414A (ja) | 2010-10-01 | 2015-12-17 | ピリミジン誘導体の製造プロセス |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013541536A JP2013541536A (ja) | 2013-11-14 |
| JP2013541536A5 true JP2013541536A5 (enExample) | 2014-11-13 |
| JP5998145B2 JP5998145B2 (ja) | 2016-09-28 |
Family
ID=44773179
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013531796A Active JP5998145B2 (ja) | 2010-10-01 | 2011-09-29 | ピリミジン誘導体の製造プロセス |
| JP2015246502A Pending JP2016106091A (ja) | 2010-10-01 | 2015-12-17 | ピリミジン誘導体の製造プロセス |
| JP2015246501A Pending JP2016128414A (ja) | 2010-10-01 | 2015-12-17 | ピリミジン誘導体の製造プロセス |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015246502A Pending JP2016106091A (ja) | 2010-10-01 | 2015-12-17 | ピリミジン誘導体の製造プロセス |
| JP2015246501A Pending JP2016128414A (ja) | 2010-10-01 | 2015-12-17 | ピリミジン誘導体の製造プロセス |
Country Status (30)
| Country | Link |
|---|---|
| US (3) | US9181215B2 (enExample) |
| EP (2) | EP2621908A2 (enExample) |
| JP (3) | JP5998145B2 (enExample) |
| KR (2) | KR20130119928A (enExample) |
| CN (3) | CN104987321A (enExample) |
| AR (1) | AR083213A1 (enExample) |
| AU (4) | AU2011308856B2 (enExample) |
| BR (1) | BR112013007123B1 (enExample) |
| CA (1) | CA2813333C (enExample) |
| CL (2) | CL2013000850A1 (enExample) |
| CO (1) | CO6700837A2 (enExample) |
| DK (1) | DK3040333T3 (enExample) |
| EC (1) | ECSP13012596A (enExample) |
| ES (1) | ES2699951T3 (enExample) |
| GT (1) | GT201300080A (enExample) |
| HU (1) | HUE041326T2 (enExample) |
| IL (3) | IL225113A (enExample) |
| LT (1) | LT3040333T (enExample) |
| MX (1) | MX354482B (enExample) |
| MY (1) | MY160785A (enExample) |
| NZ (1) | NZ608285A (enExample) |
| PE (1) | PE20140002A1 (enExample) |
| PH (2) | PH12013500579A1 (enExample) |
| PL (1) | PL3040333T3 (enExample) |
| PT (1) | PT3040333T (enExample) |
| RU (2) | RU2015150728A (enExample) |
| SG (1) | SG188439A1 (enExample) |
| SI (1) | SI3040333T1 (enExample) |
| TW (1) | TWI540133B (enExample) |
| WO (1) | WO2012044727A2 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140040770A (ko) | 2011-07-01 | 2014-04-03 | 노파르티스 아게 | 암 치료에 사용하기 위한 cdk4/6 억제제 및 pi3k 억제제를 포함하는 조합 요법 |
| PH12014500682A1 (en) | 2011-09-27 | 2014-05-12 | Novartis Ag | 3-pyrimidin-4-yl-oxazolidin-2-ones as inhibitors of mutant idh |
| UY34632A (es) | 2012-02-24 | 2013-05-31 | Novartis Ag | Compuestos de oxazolidin- 2- ona y usos de los mismos |
| ES2605638T3 (es) * | 2012-10-23 | 2017-03-15 | Novartis Ag | Proceso Mejorado para fabricar 5-(2,6-di-4-morfolinil-4-pirimidinil)-4-trifluorometilpiridin-2-amina |
| US9296733B2 (en) | 2012-11-12 | 2016-03-29 | Novartis Ag | Oxazolidin-2-one-pyrimidine derivative and use thereof for the treatment of conditions, diseases and disorders dependent upon PI3 kinases |
| WO2014141104A1 (en) | 2013-03-14 | 2014-09-18 | Novartis Ag | 3-pyrimidin-4-yl-oxazolidin-2-ones as inhibitors of mutant idh |
| US9318944B2 (en) | 2013-04-29 | 2016-04-19 | Rockwell Automation Technologies, Inc. | Methods and apparatus for active front end filter capacitor degradation detection |
| US9294005B2 (en) | 2013-10-01 | 2016-03-22 | Rockwell Automation Technologies, Inc. | Method and apparatus for detecting AFE filter capacitor degradation |
| RU2663999C2 (ru) * | 2013-10-16 | 2018-08-14 | Шанхай Инли Фармасьютикал Ко., Лтд | Конденсированное гетероциклическое соединение, способ его получения, его фармацевтическая композиция и применения |
| RU2688665C2 (ru) * | 2014-04-22 | 2019-05-22 | Университет Базель | Новый способ получения производных триазина, пиримидина и пиридина |
| CN105085476B (zh) * | 2014-11-24 | 2018-03-09 | 苏州晶云药物科技有限公司 | 5‑[2,6‑二(4‑吗啉基)‑4‑嘧啶基]‑4‑(三氟甲基)‑2‑吡啶胺二盐酸盐的晶型及其制备方法 |
| CN107001348B (zh) * | 2014-12-17 | 2019-10-11 | 上海海雁医药科技有限公司 | 2-吗啉-4,6-二取代的嘧啶衍生物、其制法与医药上的用途 |
| US9481665B2 (en) * | 2015-03-13 | 2016-11-01 | Yong Xu | Process for preparing PI3K inhibitor buparsilib |
| EP3273959A1 (en) | 2015-03-25 | 2018-01-31 | Novartis Ag | Pharmaceutical combinations |
| CN105001151B (zh) * | 2015-08-28 | 2017-07-14 | 苏州明锐医药科技有限公司 | 布帕尼西中间体及其制备方法 |
| CN106543140A (zh) * | 2015-09-21 | 2017-03-29 | 苏州晶云药物科技有限公司 | 5-[2,6-二(4-吗啉基)-4-嘧啶基]-4-(三氟甲基)-2-吡啶胺盐酸盐的晶型及其制备方法 |
| PL3978500T3 (pl) * | 2015-12-16 | 2024-03-11 | Genentech, Inc. | Sposób wytwarzania tricyklicznych związków inhibitorów pi3k |
| CN106905294A (zh) * | 2016-07-08 | 2017-06-30 | 苏州科睿思制药有限公司 | 5‑[2,6‑二(4‑吗啉基)‑4‑嘧啶基]‑4‑(三氟甲基)‑2‑吡啶胺的晶型及其制备方法 |
| CN107793394A (zh) * | 2017-08-03 | 2018-03-13 | 上海厚璞生物科技有限公司 | 一种生产选择性pi3k抑制剂的系列关键中间体 |
| CN110016142B (zh) * | 2019-04-30 | 2021-08-03 | 合肥工业大学 | 一种含嘧啶硼酸结构的硅油及其制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6124476A (en) | 1998-04-17 | 2000-09-26 | Symyx Technologies, Inc. | Catalyst ligands, catalyst compositions, catalyst metal complexes and processes for cross-coupling aromatic boron compounds with aromatic halogens or perfluoroalkylsulfonates |
| CN1735598A (zh) * | 2002-11-11 | 2006-02-15 | 拜耳医药保健股份公司 | 作为ip受体拮抗剂的苯基或杂芳基氨基烷烃衍生物 |
| CA2507100C (en) | 2002-11-21 | 2012-10-09 | Chiron Corporation | 2,4,6-trisubstituted pyrimidines as phosphotidylinositol (pi) 3-kinase inhibitors and their use in the treatment of cancer |
| JO2660B1 (en) * | 2006-01-20 | 2012-06-17 | نوفارتيس ايه جي | Pi-3 inhibitors and methods of use |
| EP2057140B1 (en) | 2006-08-24 | 2012-08-08 | AstraZeneca AB | Morpholino pyrimidine derivatives useful in the treatment of proliferative disorders |
| MX2009008341A (es) * | 2007-02-06 | 2009-08-12 | Novartis Ag | Inhibidores de cinasa de pi3 y metodos para su uso. |
| WO2009066084A1 (en) * | 2007-11-21 | 2009-05-28 | F. Hoffmann-La Roche Ag | 2 -morpholinopyrimidines and their use as pi3 kinase inhibitors |
| JP2012526772A (ja) * | 2009-05-15 | 2012-11-01 | ノバルティス アーゲー | ホスホイノシチド３−キナーゼ阻害剤および抗糖尿病性化合物の組合せ剤 |
-
2011
- 2011-09-29 PE PE2013000654A patent/PE20140002A1/es active IP Right Grant
- 2011-09-29 MY MYPI2013000811A patent/MY160785A/en unknown
- 2011-09-29 RU RU2015150728A patent/RU2015150728A/ru unknown
- 2011-09-29 CA CA2813333A patent/CA2813333C/en active Active
- 2011-09-29 PH PH1/2013/500579A patent/PH12013500579A1/en unknown
- 2011-09-29 KR KR1020137011172A patent/KR20130119928A/ko not_active Ceased
- 2011-09-29 AR ARP110103595A patent/AR083213A1/es unknown
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