JP2013532668A5 - - Google Patents
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- Publication number
- JP2013532668A5 JP2013532668A5 JP2013520993A JP2013520993A JP2013532668A5 JP 2013532668 A5 JP2013532668 A5 JP 2013532668A5 JP 2013520993 A JP2013520993 A JP 2013520993A JP 2013520993 A JP2013520993 A JP 2013520993A JP 2013532668 A5 JP2013532668 A5 JP 2013532668A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- ethyl
- methylamino
- substituted methylene
- monosubstituted
- 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.)
- Granted
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 48
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 28
- 239000012453 solvate Substances 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 12
- 230000001419 dependent effect Effects 0.000 claims 11
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 10
- 239000000651 prodrug Substances 0.000 claims 10
- 229940002612 prodrug Drugs 0.000 claims 10
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims 6
- -1 methyl-substituted methylene Chemical group 0.000 claims 5
- 125000004434 sulfur atom Chemical group 0.000 claims 5
- 230000033115 angiogenesis Effects 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 4
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 201000004624 Dermatitis Diseases 0.000 claims 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 2
- 208000032612 Glial tumor Diseases 0.000 claims 2
- 206010018338 Glioma Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 208000007766 Kaposi sarcoma Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 206010033645 Pancreatitis Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 206010038933 Retinopathy of prematurity Diseases 0.000 claims 2
- 206010039710 Scleroderma Diseases 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 206010064930 age-related macular degeneration Diseases 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 208000010668 atopic eczema Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 201000011066 hemangioma Diseases 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 206010020718 hyperplasia Diseases 0.000 claims 2
- 230000003463 hyperproliferative effect Effects 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
- 208000002780 macular degeneration Diseases 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 210000002307 prostate Anatomy 0.000 claims 2
- 208000037803 restenosis Diseases 0.000 claims 2
- 208000017520 skin disease Diseases 0.000 claims 2
- 230000005747 tumor angiogenesis Effects 0.000 claims 2
- FLGUGRAWIWHCJF-MRXNPFEDSA-N 2-ethyl-4-[[(1s)-1-(3-fluorophenyl)-2-(methylamino)ethyl]amino]quinazoline-8-carboxamide Chemical compound C1([C@@H](CNC)NC=2N=C(N=C3C(C(N)=O)=CC=CC3=2)CC)=CC=CC(F)=C1 FLGUGRAWIWHCJF-MRXNPFEDSA-N 0.000 claims 1
- SKSIVYGMKXKZAL-MRXNPFEDSA-N 2-ethyl-4-[[(1s)-1-(4-fluorophenyl)-2-(methylamino)ethyl]amino]quinazoline-8-carboxamide Chemical compound C1([C@@H](CNC)NC=2N=C(N=C3C(C(N)=O)=CC=CC3=2)CC)=CC=C(F)C=C1 SKSIVYGMKXKZAL-MRXNPFEDSA-N 0.000 claims 1
- DMIFTASZHIOFDS-MRXNPFEDSA-N 2-ethyl-4-[[(1s)-2-(methylamino)-1-phenylethyl]amino]quinazoline-8-carboxamide Chemical compound C1([C@@H](CNC)NC=2N=C(N=C3C(C(N)=O)=CC=CC3=2)CC)=CC=CC=C1 DMIFTASZHIOFDS-MRXNPFEDSA-N 0.000 claims 1
- POFQBVKRYMOMRR-MRXNPFEDSA-N 2-methyl-4-[[(1s)-2-(methylamino)-1-phenylethyl]amino]quinazoline-8-carboxamide Chemical compound C1([C@H](NC=2C3=CC=CC(=C3N=C(C)N=2)C(N)=O)CNC)=CC=CC=C1 POFQBVKRYMOMRR-MRXNPFEDSA-N 0.000 claims 1
- KDWHIHJILMZLQT-MRXNPFEDSA-N 4-[(2s)-3-(azetidin-1-yl)-2-(3-chlorophenyl)propyl]-2-ethylquinazoline-8-carboxamide Chemical compound C([C@@H](CC=1N=C(N=C2C(C(N)=O)=CC=CC2=1)CC)C=1C=C(Cl)C=CC=1)N1CCC1 KDWHIHJILMZLQT-MRXNPFEDSA-N 0.000 claims 1
- GICHDAPJTGXHJB-MRXNPFEDSA-N 4-[(2s)-3-(azetidin-1-yl)-2-(3-chlorophenyl)propyl]-2-methylquinazoline-8-carboxamide Chemical compound C([C@@H](CC=1N=C(N=C2C(C(N)=O)=CC=CC2=1)C)C=1C=C(Cl)C=CC=1)N1CCC1 GICHDAPJTGXHJB-MRXNPFEDSA-N 0.000 claims 1
- DVDSKHYUBCNSOF-MRXNPFEDSA-N 4-[(2s)-3-(azetidin-1-yl)-2-(3-fluorophenyl)propyl]-2-ethylquinazoline-8-carboxamide Chemical compound C([C@@H](CC=1N=C(N=C2C(C(N)=O)=CC=CC2=1)CC)C=1C=C(F)C=CC=1)N1CCC1 DVDSKHYUBCNSOF-MRXNPFEDSA-N 0.000 claims 1
- FNHYSUBXBFOTCI-MRXNPFEDSA-N 4-[(2s)-3-(azetidin-1-yl)-2-(3-fluorophenyl)propyl]-2-methylquinazoline-8-carboxamide Chemical compound C([C@@H](CC=1N=C(N=C2C(C(N)=O)=CC=CC2=1)C)C=1C=C(F)C=CC=1)N1CCC1 FNHYSUBXBFOTCI-MRXNPFEDSA-N 0.000 claims 1
- LJTQGHLIYHSMOX-MRXNPFEDSA-N 4-[(2s)-3-(azetidin-1-yl)-2-(4-chlorophenyl)propyl]-2-ethylquinazoline-8-carboxamide Chemical compound C([C@@H](CC=1N=C(N=C2C(C(N)=O)=CC=CC2=1)CC)C=1C=CC(Cl)=CC=1)N1CCC1 LJTQGHLIYHSMOX-MRXNPFEDSA-N 0.000 claims 1
- LPMREZWHAIEKQZ-MRXNPFEDSA-N 4-[(2s)-3-(azetidin-1-yl)-2-(4-chlorophenyl)propyl]-2-methylquinazoline-8-carboxamide Chemical compound C([C@@H](CC=1N=C(N=C2C(C(N)=O)=CC=CC2=1)C)C=1C=CC(Cl)=CC=1)N1CCC1 LPMREZWHAIEKQZ-MRXNPFEDSA-N 0.000 claims 1
- TVXPEQKGAHYKQO-MRXNPFEDSA-N 4-[(2s)-3-(azetidin-1-yl)-2-(4-fluorophenyl)propyl]-2-ethylquinazoline-8-carboxamide Chemical compound C([C@@H](CC=1N=C(N=C2C(C(N)=O)=CC=CC2=1)CC)C=1C=CC(F)=CC=1)N1CCC1 TVXPEQKGAHYKQO-MRXNPFEDSA-N 0.000 claims 1
- OSVXDIAAYFUGBW-MRXNPFEDSA-N 4-[(2s)-3-(azetidin-1-yl)-2-(4-fluorophenyl)propyl]-2-methylquinazoline-8-carboxamide Chemical compound C([C@@H](CC=1N=C(N=C2C(C(N)=O)=CC=CC2=1)C)C=1C=CC(F)=CC=1)N1CCC1 OSVXDIAAYFUGBW-MRXNPFEDSA-N 0.000 claims 1
- PSVWDJSMYZACCK-QGZVFWFLSA-N 4-[(2s)-3-(azetidin-1-yl)-2-phenylpropyl]-2-ethylquinazoline-8-carboxamide Chemical compound C([C@@H](CC=1N=C(N=C2C(C(N)=O)=CC=CC2=1)CC)C=1C=CC=CC=1)N1CCC1 PSVWDJSMYZACCK-QGZVFWFLSA-N 0.000 claims 1
- KVZQADFWZCYYQV-QGZVFWFLSA-N 4-[(2s)-3-(azetidin-1-yl)-2-phenylpropyl]-2-methylquinazoline-8-carboxamide Chemical compound C([C@@H](CC=1N=C(N=C2C(C(N)=O)=CC=CC2=1)C)C=1C=CC=CC=1)N1CCC1 KVZQADFWZCYYQV-QGZVFWFLSA-N 0.000 claims 1
- GZSKSABPMQXDBI-MRXNPFEDSA-N 4-[[(1s)-1-(3-chlorophenyl)-2-(methylamino)ethyl]amino]-2-ethylquinazoline-8-carboxamide Chemical compound C1([C@@H](CNC)NC=2N=C(N=C3C(C(N)=O)=CC=CC3=2)CC)=CC=CC(Cl)=C1 GZSKSABPMQXDBI-MRXNPFEDSA-N 0.000 claims 1
- TUGQXVDVBAIMQT-MRXNPFEDSA-N 4-[[(1s)-1-(3-chlorophenyl)-2-(methylamino)ethyl]amino]-2-methylquinazoline-8-carboxamide Chemical compound C1([C@H](NC=2C3=CC=CC(=C3N=C(C)N=2)C(N)=O)CNC)=CC=CC(Cl)=C1 TUGQXVDVBAIMQT-MRXNPFEDSA-N 0.000 claims 1
- GDZSUVPAQIUIGI-CQSZACIVSA-N 4-[[(1s)-1-(3-fluorophenyl)-2-(methylamino)ethyl]amino]-2-(trifluoromethyl)quinazoline-8-carboxamide Chemical compound C1([C@H](NC=2C3=CC=CC(=C3N=C(N=2)C(F)(F)F)C(N)=O)CNC)=CC=CC(F)=C1 GDZSUVPAQIUIGI-CQSZACIVSA-N 0.000 claims 1
- DSLKQMBMFBKGRK-MRXNPFEDSA-N 4-[[(1s)-1-(3-fluorophenyl)-2-(methylamino)ethyl]amino]-2-methylquinazoline-8-carboxamide Chemical compound C1([C@H](NC=2C3=CC=CC(=C3N=C(C)N=2)C(N)=O)CNC)=CC=CC(F)=C1 DSLKQMBMFBKGRK-MRXNPFEDSA-N 0.000 claims 1
- NMCWJLCHHFXWFC-MRXNPFEDSA-N 4-[[(1s)-1-(4-chlorophenyl)-2-(methylamino)ethyl]amino]-2-ethylquinazoline-8-carboxamide Chemical compound C1([C@@H](CNC)NC=2N=C(N=C3C(C(N)=O)=CC=CC3=2)CC)=CC=C(Cl)C=C1 NMCWJLCHHFXWFC-MRXNPFEDSA-N 0.000 claims 1
- NDQZVNOJBBXGOJ-MRXNPFEDSA-N 4-[[(1s)-1-(4-chlorophenyl)-2-(methylamino)ethyl]amino]-2-methylquinazoline-8-carboxamide Chemical compound C1([C@H](NC=2C3=CC=CC(=C3N=C(C)N=2)C(N)=O)CNC)=CC=C(Cl)C=C1 NDQZVNOJBBXGOJ-MRXNPFEDSA-N 0.000 claims 1
- PYWWWUCMNVNQOM-QGZVFWFLSA-N 4-[[(1s)-1-(4-chlorophenyl)-2-(methylamino)ethyl]amino]-2-propan-2-ylquinazoline-8-carboxamide Chemical compound C1([C@H](NC=2C3=CC=CC(=C3N=C(N=2)C(C)C)C(N)=O)CNC)=CC=C(Cl)C=C1 PYWWWUCMNVNQOM-QGZVFWFLSA-N 0.000 claims 1
- SWJLPMOSDVXEPJ-MRXNPFEDSA-N 4-[[(1s)-1-(4-fluorophenyl)-2-(methylamino)ethyl]amino]-2-methylquinazoline-8-carboxamide Chemical compound C1([C@H](NC=2C3=CC=CC(=C3N=C(C)N=2)C(N)=O)CNC)=CC=C(F)C=C1 SWJLPMOSDVXEPJ-MRXNPFEDSA-N 0.000 claims 1
- 125000000815 N-oxide group Chemical group 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36896410P | 2010-07-29 | 2010-07-29 | |
| US61/368,964 | 2010-07-29 | ||
| PCT/EP2011/003272 WO2012013282A1 (en) | 2010-07-29 | 2011-07-01 | Bicyclic azaheterocyclic carboxamides as inhibitors of the kinase p70s6k |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013532668A JP2013532668A (ja) | 2013-08-19 |
| JP2013532668A5 true JP2013532668A5 (cg-RX-API-DMAC10.html) | 2014-08-14 |
| JP5894157B2 JP5894157B2 (ja) | 2016-03-23 |
Family
ID=44532723
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013520993A Expired - Fee Related JP5894157B2 (ja) | 2010-07-29 | 2011-07-01 | キナーゼp70S6Kの阻害剤としての二環式アザ複素環式カルボキサミド |
Country Status (18)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8563573B2 (en) | 2007-11-02 | 2013-10-22 | Vertex Pharmaceuticals Incorporated | Azaindole derivatives as CFTR modulators |
| US8802868B2 (en) | 2010-03-25 | 2014-08-12 | Vertex Pharmaceuticals Incorporated | Solid forms of (R)-1(2,2-difluorobenzo[D][1,3]dioxo1-5-yl)-N-(1-(2,3-dihydroxypropyl-6-fluoro-2-(1-hydroxy-2-methylpropan2-yl)-1H-Indol-5-yl)-Cyclopropanecarboxamide |
| EP3381899B1 (en) | 2010-04-22 | 2021-01-06 | Vertex Pharmaceuticals Incorporated | Intermediate compound for process of producing cycloalkylcarboxamido-indole compounds |
| WO2012016001A1 (en) * | 2010-07-29 | 2012-02-02 | Merck Patent Gmbh | Cyclic amine azaheterocyclic carboxamides |
| KR101894116B1 (ko) * | 2010-11-24 | 2018-08-31 | 메르크 파텐트 게엠베하 | 퀴나졸린 카르복사미드 아제티딘 |
| EP2755965B1 (en) | 2011-09-12 | 2017-07-26 | Merck Patent GmbH | Novel imidazole amines as modulators of kinase activity |
| CN103930407B (zh) | 2011-09-12 | 2019-02-26 | 默克专利有限公司 | 用作激酶活性调节剂的氨基嘧啶衍生物 |
| ES2620119T3 (es) | 2012-11-16 | 2017-06-27 | Merck Patent Gmbh | Derivados heterocíclicos novedosos como moduladores de la actividad de quinasa |
| CA2890345A1 (en) | 2012-11-16 | 2014-05-22 | Merck Patent Gmbh | Imidazol-piperidinyl derivatives as modulators of kinase activity |
| WO2014085528A1 (en) * | 2012-11-29 | 2014-06-05 | Merck Patent Gmbh | Azaquinazoline carboxamide derivatives |
| HK1218756A1 (zh) | 2013-03-11 | 2017-03-10 | 默克专利有限公司 | 用作激酶活性调节剂的6-[4-(1h-咪唑-2-基)哌啶-1-基]嘧啶-4-胺衍生物 |
| CN103232401B (zh) * | 2013-04-12 | 2015-11-04 | 浙江工业大学 | 一种4-芳硫基喹唑啉类化合物的合成方法 |
| CN103254141B (zh) * | 2013-04-26 | 2016-02-24 | 浙江工业大学 | 4-[4-(2-二丙氨基乙酰氨基)苯胺基]-6-取代喹唑啉类化合物及制备和应用 |
| AU2015240094B2 (en) | 2014-04-03 | 2020-07-30 | Merck Patent Gmbh | Combinations of cancer therapeutics |
| JP6543268B2 (ja) | 2014-04-15 | 2019-07-10 | バーテックス ファーマシューティカルズ インコーポレイテッドVertex Pharmaceuticals Incorporated | 嚢胞性線維症膜コンダクタンス調節因子が媒介する疾患を処置するための医薬組成物 |
| EP4138779A4 (en) * | 2020-04-21 | 2024-05-22 | University of Massachusetts | Methods and compositions for treatment of age-related macular degeneration |
| EP4243819A1 (en) | 2020-11-16 | 2023-09-20 | Merck Patent GmbH | Kinase inhibitor combinations for cancer treatment |
| WO2023039068A1 (en) * | 2021-09-08 | 2023-03-16 | Neubase Therapeutics, Inc. | Compositions and methods for synthesis of peptide nucleic acid intermediates |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9613021D0 (en) * | 1996-06-21 | 1996-08-28 | Pharmacia Spa | Bicyclic 4-aralkylaminopyrimidine derivatives as tyrosine kinase inhibitors |
| AR016817A1 (es) * | 1997-08-14 | 2001-08-01 | Smithkline Beecham Plc | Derivados de fenilurea o feniltiourea, procedimiento para su preparacion, coleccion de compuestos, compuestos intermediarios, composicion farmaceutica,metodo de tratamiento y uso de dichos compuestos para la manufactura de un medicamento |
| KR100774855B1 (ko) * | 2000-04-27 | 2007-11-08 | 아스텔라스세이야쿠 가부시키가이샤 | 축합 헤테로아릴 유도체 |
| TW200306819A (en) | 2002-01-25 | 2003-12-01 | Vertex Pharma | Indazole compounds useful as protein kinase inhibitors |
| JPWO2004014861A1 (ja) * | 2002-08-09 | 2005-12-02 | 杏林製薬株式会社 | 4−置換キノリン−8−カルボン酸アミド誘導体とその薬理上許容される付加塩 |
| AU2003252314A1 (en) * | 2002-08-09 | 2004-02-25 | Kyorin Pharmaceutical Co., Ltd. | 4-substituted quinazoline-8-carboxyamide derivative and pharmaceutically acceptable addition salt thereof |
| JP2006522124A (ja) | 2003-04-03 | 2006-09-28 | バーテックス ファーマシューティカルズ インコーポレイテッド | プロテインキナーゼのインヒビターとして有用な組成物 |
| CN100412066C (zh) | 2003-09-30 | 2008-08-20 | Irm责任有限公司 | 用作蛋白激酶抑制剂的化合物和组合物 |
| JP4800216B2 (ja) | 2003-10-24 | 2011-10-26 | エグゼリクシス, インコーポレイテッド | p70S6キナーゼモジュレーターおよび使用方法 |
| CA2546117A1 (en) | 2003-11-21 | 2005-06-16 | Novartis Ag | 1h-imidazoquinoline derivatives as protein kinase inhibitors |
| CA2546920A1 (en) | 2003-12-09 | 2005-06-23 | Joel Moss | Methods for suppressing an immune response or treating a proliferative disorder |
| CA2563699C (en) | 2004-04-23 | 2014-03-25 | Exelixis, Inc. | Kinase modulators and method of use |
| AU2005251735A1 (en) * | 2004-06-04 | 2005-12-22 | Amphora Discovery Corporation | Quinoline- and isoquinoline-based compounds exhibiting ATP-utilizing enzyme inhibitory activity, and compositions, and uses thereof |
| JP5274842B2 (ja) | 2004-12-28 | 2013-08-28 | エグゼリクシス, インコーポレイテッド | 免疫疾患、炎症疾患および増殖疾患の処置のためのセリン−スレオニンキナーゼモジュレーター(p70S6K、Akt−1およびAkt−2)としての[1H−ピペラゾ[3,4−d]ピリミジン−4−イル]−ピペラジンまたは[1H−ピペラゾ[3,4−d]ピリミジン−4−イル]−ピペラジン化合物 |
| GB0501999D0 (en) | 2005-02-01 | 2005-03-09 | Sentinel Oncology Ltd | Pharmaceutical compounds |
| WO2006136821A1 (en) | 2005-06-22 | 2006-12-28 | Astex Therapeutics Limited | Pharmaceutical compounds |
| UA99284C2 (ru) | 2007-05-11 | 2012-08-10 | Елі Ліллі Енд Компані | ИНГИБИТОРЫ р70 S6-КИНАЗЫ |
| KR101699991B1 (ko) * | 2009-02-11 | 2017-01-26 | 메르크 파텐트 게엠베하 | 신규의 아미노 아자헤테로시클릭 카르복사미드 |
-
2011
- 2011-01-07 UA UAA201302432A patent/UA110113C2/uk unknown
- 2011-07-01 CA CA2806610A patent/CA2806610C/en active Active
- 2011-07-01 EP EP11738160.8A patent/EP2598492B1/en active Active
- 2011-07-01 ES ES11738160.8T patent/ES2557383T3/es active Active
- 2011-07-01 EA EA201300186A patent/EA023132B1/ru not_active IP Right Cessation
- 2011-07-01 AU AU2011285247A patent/AU2011285247B2/en not_active Ceased
- 2011-07-01 JP JP2013520993A patent/JP5894157B2/ja not_active Expired - Fee Related
- 2011-07-01 KR KR1020137005466A patent/KR101852644B1/ko not_active Expired - Fee Related
- 2011-07-01 NZ NZ604379A patent/NZ604379A/en not_active IP Right Cessation
- 2011-07-01 CN CN201180037284.6A patent/CN103003250B/zh not_active Expired - Fee Related
- 2011-07-01 BR BR112013002090A patent/BR112013002090A2/pt active Search and Examination
- 2011-07-01 US US13/703,276 patent/US8710044B2/en active Active
- 2011-07-01 WO PCT/EP2011/003272 patent/WO2012013282A1/en not_active Ceased
- 2011-07-01 MX MX2013001054A patent/MX2013001054A/es active IP Right Grant
- 2011-07-01 SG SG2013004965A patent/SG187166A1/en unknown
- 2011-07-29 AR ARP110102741A patent/AR082414A1/es active IP Right Grant
-
2012
- 2012-12-31 IL IL224072A patent/IL224072A/en active IP Right Grant
-
2013
- 2013-01-28 CL CL2013000263A patent/CL2013000263A1/es unknown