CA2776028C - Pyrrolo[2,3-d]pyrimidine compounds - Google Patents
Pyrrolo[2,3-d]pyrimidine compounds Download PDFInfo
- Publication number
- CA2776028C CA2776028C CA2776028A CA2776028A CA2776028C CA 2776028 C CA2776028 C CA 2776028C CA 2776028 A CA2776028 A CA 2776028A CA 2776028 A CA2776028 A CA 2776028A CA 2776028 C CA2776028 C CA 2776028C
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- pyrrolo
- pyrimidin
- trans
- cyclohexyl
- 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.)
- Expired - Fee Related
Links
- 150000004943 pyrrolo[2,3-d]pyrimidines Chemical class 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 263
- 108010024121 Janus Kinases Proteins 0.000 claims abstract description 58
- 102000015617 Janus Kinases Human genes 0.000 claims abstract description 58
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
- -1 cyano, phenyl Chemical group 0.000 claims description 245
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 190
- 229910052739 hydrogen Inorganic materials 0.000 claims description 188
- 239000001257 hydrogen Substances 0.000 claims description 188
- 150000003839 salts Chemical class 0.000 claims description 122
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 113
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 109
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 99
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 94
- 125000001424 substituent group Chemical group 0.000 claims description 90
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 87
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 77
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 70
- 125000003118 aryl group Chemical group 0.000 claims description 66
- 125000000623 heterocyclic group Chemical group 0.000 claims description 54
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 53
- 125000005843 halogen group Chemical group 0.000 claims description 52
- 238000011282 treatment Methods 0.000 claims description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 42
- 125000004076 pyridyl group Chemical group 0.000 claims description 41
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 41
- 125000001153 fluoro group Chemical group F* 0.000 claims description 39
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
- 230000001404 mediated effect Effects 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 125000004043 oxo group Chemical group O=* 0.000 claims description 23
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 21
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 125000004193 piperazinyl group Chemical group 0.000 claims description 19
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 17
- 208000006673 asthma Diseases 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 206010052779 Transplant rejections Diseases 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 13
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 13
- 230000005764 inhibitory process Effects 0.000 claims description 13
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 13
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 13
- 201000006417 multiple sclerosis Diseases 0.000 claims description 13
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 13
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 13
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 11
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 208000023275 Autoimmune disease Diseases 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 208000035475 disorder Diseases 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 206010012601 diabetes mellitus Diseases 0.000 claims description 9
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 210000000056 organ Anatomy 0.000 claims description 9
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 8
- 206010020751 Hypersensitivity Diseases 0.000 claims description 7
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
- 230000001363 autoimmune Effects 0.000 claims description 7
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 7
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 7
- IZXWMVPZODQBRB-UHFFFAOYSA-N piperidine-3,4-diol Chemical compound OC1CCNCC1O IZXWMVPZODQBRB-UHFFFAOYSA-N 0.000 claims description 7
- 125000003386 piperidinyl group Chemical group 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 6
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- 230000007815 allergy Effects 0.000 claims description 6
- 125000002393 azetidinyl group Chemical group 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
- 208000032839 leukemia Diseases 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
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- 230000001684 chronic effect Effects 0.000 claims description 5
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- YWEMBZPSYGFVOH-UHFFFAOYSA-N 3-methyl-4-(phenylmethoxycarbonylamino)benzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1NC(=O)OCC1=CC=CC=C1 YWEMBZPSYGFVOH-UHFFFAOYSA-N 0.000 claims description 4
- CNUBKBHAGWYWKC-QAQDUYKDSA-N C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1CCC(CO)CC1 Chemical compound C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1CCC(CO)CC1 CNUBKBHAGWYWKC-QAQDUYKDSA-N 0.000 claims description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
- 208000011231 Crohn disease Diseases 0.000 claims description 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
- 208000034578 Multiple myelomas Diseases 0.000 claims description 4
- 208000033759 Prolymphocytic T-Cell Leukemia Diseases 0.000 claims description 4
- 206010060862 Prostate cancer Diseases 0.000 claims description 4
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 4
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 4
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 4
- 206010040047 Sepsis Diseases 0.000 claims description 4
- 208000026651 T-cell prolymphocytic leukemia Diseases 0.000 claims description 4
- 210000001744 T-lymphocyte Anatomy 0.000 claims description 4
- 206010046851 Uveitis Diseases 0.000 claims description 4
- 230000001154 acute effect Effects 0.000 claims description 4
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- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- DFVBZOPVGGDURA-UYSNPLJNSA-N (3r)-1-[[4-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl]methylsulfonyl]piperidin-3-ol Chemical compound N=1C=NC=2NC=CC=2C=1N(C)C(CC1)CCC1CS(=O)(=O)N1CCC[C@@H](O)C1 DFVBZOPVGGDURA-UYSNPLJNSA-N 0.000 claims description 3
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 206010025135 lupus erythematosus Diseases 0.000 claims description 3
- 125000006626 methoxycarbonylamino group Chemical group 0.000 claims description 3
- 230000003612 virological effect Effects 0.000 claims description 3
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 42
- FNYKNWAPYCCIQE-VNHLFDKOSA-N C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1CCC(C)(O)C1 Chemical compound C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1CCC(C)(O)C1 FNYKNWAPYCCIQE-VNHLFDKOSA-N 0.000 claims 4
- QMHIFZZTSBMKGF-NXOAAHMSSA-N C1[C@H](CO)[C@@H](C)CN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 Chemical compound C1[C@H](CO)[C@@H](C)CN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 QMHIFZZTSBMKGF-NXOAAHMSSA-N 0.000 claims 4
- 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 4
- RRWIERVKMPBTBE-HPFXQQBRSA-N (3r)-1-[[(1s,3r,4s)-3-methyl-4-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl]methylsulfonyl]piperidin-3-ol Chemical compound C([C@@H]1C[C@H]([C@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)C)S(=O)(=O)N1CCC[C@@H](O)C1 RRWIERVKMPBTBE-HPFXQQBRSA-N 0.000 claims 2
- RRWIERVKMPBTBE-CVYDXHPNSA-N (3s)-1-[[(1s,3r,4s)-3-methyl-4-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl]methylsulfonyl]piperidin-3-ol Chemical compound C([C@@H]1C[C@H]([C@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)C)S(=O)(=O)N1CCC[C@H](O)C1 RRWIERVKMPBTBE-CVYDXHPNSA-N 0.000 claims 2
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- SRPNJZWTHJDMHK-CTWPCTMYSA-N [(3r)-1-[[4-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl]methylsulfonyl]piperidin-3-yl] 2,2-dimethylpropanoate Chemical compound N=1C=NC=2NC=CC=2C=1N(C)C(CC1)CCC1CS(=O)(=O)N1CCC[C@@H](OC(=O)C(C)(C)C)C1 SRPNJZWTHJDMHK-CTWPCTMYSA-N 0.000 claims 2
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- UCALNVLMEPQUKV-SOAGJPPSSA-N diethyl [(3r)-1-[[4-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl]methylsulfonyl]piperidin-3-yl] phosphate Chemical compound C1[C@H](OP(=O)(OCC)OCC)CCCN1S(=O)(=O)CC1CCC(N(C)C=2C=3C=CNC=3N=CN=2)CC1 UCALNVLMEPQUKV-SOAGJPPSSA-N 0.000 claims 2
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 2
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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| AU2010227225A1 (en) | 2009-03-23 | 2011-09-15 | Glenmark Pharmaceuticals, S.A. | Furopyrimidinedione derivatives as TRPA1 modulators |
| CA2767253A1 (en) | 2009-07-06 | 2011-01-13 | Ontorii, Inc. | Novel nucleic acid prodrugs and methods of use thereof |
| TW201111385A (en) * | 2009-08-27 | 2011-04-01 | Biocryst Pharm Inc | Heterocyclic compounds as janus kinase inhibitors |
| CA2782720A1 (en) * | 2009-12-18 | 2011-06-23 | Pfizer Inc. | Pyrrolo[2,3-d]pyrimidine compounds |
| WO2012039448A1 (ja) * | 2010-09-24 | 2012-03-29 | 株式会社キラルジェン | 不斉補助基 |
| CN103796657B (zh) | 2011-07-19 | 2017-07-11 | 波涛生命科学有限公司 | 合成官能化核酸的方法 |
| TWI601727B (zh) | 2011-08-12 | 2017-10-11 | 日產化學工業股份有限公司 | 三環雜環化合物及ｊａｋ（傑納斯激酶）抑制劑 |
| WO2014010250A1 (en) | 2012-07-13 | 2014-01-16 | Chiralgen, Ltd. | Asymmetric auxiliary group |
| CA2879066C (en) | 2012-07-13 | 2019-08-13 | Shin Nippon Biomedical Laboratories, Ltd. | Chiral nucleic acid adjuvant |
| JP6453212B2 (ja) | 2012-07-13 | 2019-01-16 | ウェイブ ライフ サイエンシズ リミテッドＷａｖｅ Ｌｉｆｅ Ｓｃｉｅｎｃｅｓ Ｌｔｄ． | キラル制御 |
| MY173845A (en) * | 2012-07-17 | 2020-02-24 | Glaxosmithkline Ip No 2 Ltd | Indolecarbonitriles as selective androgen receptor modulators |
| CN103896946B (zh) * | 2012-12-28 | 2018-04-03 | 浙江导明医药科技有限公司 | 用于预防及治疗多种自身免疫疾病的新化合物 |
| EP2951590A1 (en) | 2013-02-04 | 2015-12-09 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for assaying jak2 activity in red blood cells and uses thereof |
| ES2755130T3 (es) | 2013-02-08 | 2020-04-21 | Nissan Chemical Corp | Compuesto de pirrolopiridina tricíclico, e inhibidor de JAK |
| EP2958921B1 (en) | 2013-02-22 | 2017-09-20 | Pfizer Inc | Pyrrolo [2, 3 -d]pyrimidine derivatives as inhibitors of janus kinases (jak) |
| MY182237A (en) | 2013-05-02 | 2021-01-18 | Hoffmann La Roche | Pyrrolo[2,3-d]pyrimidine derivatives as cb2 receptor agonists |
| JPWO2015108046A1 (ja) | 2014-01-15 | 2017-03-23 | 株式会社新日本科学 | 抗アレルギー作用を有するキラル核酸アジュバンド及び抗アレルギー剤 |
| JPWO2015108048A1 (ja) | 2014-01-15 | 2017-03-23 | 株式会社新日本科学 | 抗腫瘍作用を有するキラル核酸アジュバンド及び抗腫瘍剤 |
| WO2015108047A1 (ja) | 2014-01-15 | 2015-07-23 | 株式会社新日本科学 | 免疫誘導活性を有するキラル核酸アジュバンド及び免疫誘導活性剤 |
| KR20230152178A (ko) | 2014-01-16 | 2023-11-02 | 웨이브 라이프 사이언시스 리미티드 | 키랄 디자인 |
| EP2924026A1 (en) | 2014-03-28 | 2015-09-30 | Novartis Tiergesundheit AG | Aminosulfonylmethylcyclohexanes as JAK inhibitors |
| MY182812A (en) | 2014-05-14 | 2021-02-05 | Nissan Chemical Ind Ltd | Tricyclic compound and jak inhibitor |
| EP3180344B1 (en) | 2014-08-12 | 2019-09-18 | Pfizer Inc | Pyrrolo[2,3-d]pyrimidine derivatives useful for inhibiting janus kinase |
| EP3416965B1 (en) * | 2016-02-16 | 2020-10-07 | Zoetis Services LLC | Process for preparing 7h-pyrrolo [2,3-d]pyrimidine compounds |
| CN107098908B (zh) * | 2016-02-23 | 2021-01-08 | 欣凯医药科技(上海)有限公司 | 一种吡咯并嘧啶类化合物的制备方法和应用 |
| WO2018167283A1 (en) | 2017-03-17 | 2018-09-20 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for the diagnosis and treatment of pancreatic ductal adenocarcinoma associated neural remodeling |
| US20200088732A1 (en) | 2017-04-13 | 2020-03-19 | INSERM (Institut National de la Santé et de la Recherche Mèdicale) | Methods for the diagnosis and treatment of pancreatic ductal adenocarcinoma |
| WO2020092015A1 (en) | 2018-11-02 | 2020-05-07 | University Of Rochester | Therapeutic mitigation of epithelial infection |
| KR102857917B1 (ko) * | 2019-01-30 | 2025-09-10 | 펠리카메드 바이오테크놀로지 컴퍼니 리미티드 | Jak 억제제 및 그 제조 방법 |
| IL264854A (en) * | 2019-02-14 | 2020-08-31 | Bahat Anat | Spt5 inhibitors and methods of use thereof |
| WO2021003084A1 (en) * | 2019-07-01 | 2021-01-07 | Ligang Qian | P2x7r antagonists |
| PL4021452T3 (pl) * | 2019-08-26 | 2024-05-06 | Chemwerth Inc | Podstawione związki (7h-pirolo[2,3-d]pirymidyn-4-ylo)aminowe przydatne jako inhibitory jak1 |
| US20220372135A1 (en) | 2019-09-27 | 2022-11-24 | Disc Medicine, Inc. | Methods for treating myelofibrosis and related conditions |
| IL297437A (en) | 2020-05-13 | 2022-12-01 | Disc Medicine Inc | Anti-hemojuvelin (hjv) antibodies for treating myelofibrosis |
| CN115246833B (zh) * | 2021-04-27 | 2024-08-13 | 洛阳惠中兽药有限公司 | 一种奥拉替尼化合物及其中间体化合物的制备方法 |
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| CZ20004727A3 (cs) | 1998-06-19 | 2002-03-13 | Pfizer Products Inc. | Deriváty pyrrolo[2,3-d] pyrimidinu |
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| AU777911B2 (en) | 1999-12-10 | 2004-11-04 | Pfizer Products Inc. | Pyrrolo(2,3-d)pyrimidine compounds |
| UA74370C2 (uk) * | 2000-06-26 | 2005-12-15 | Пфайзер Продактс Інк. | Піроло(2,3-d)піримідинові сполуки як імуносупресори |
| US7301023B2 (en) | 2001-05-31 | 2007-11-27 | Pfizer Inc. | Chiral salt resolution |
| BR0316470A (pt) | 2002-11-21 | 2005-10-11 | Pfizer Prod Inc | Derivados de 3-amino-piperadina e métodos de preparação |
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| CN105348203B (zh) | 2005-06-08 | 2018-09-18 | 里格尔药品股份有限公司 | 抑制jak途径的组合物和方法 |
| CN102127078A (zh) | 2005-07-14 | 2011-07-20 | 安斯泰来制药株式会社 | Janus激酶3的杂环类抑制剂 |
| PL1913000T3 (pl) | 2005-07-29 | 2012-05-31 | Pfizer Prod Inc | Pochodne pirolo[2,3-d]pirymidyny, ich związki pośrednie i synteza |
| ES2401192T3 (es) | 2005-09-30 | 2013-04-17 | Vertex Pharmceuticals Incorporated | Deazapurinas útiles como inhibidores de janus cinasas |
| DK1951684T3 (en) | 2005-11-01 | 2016-10-24 | Targegen Inc | BIARYLMETAPYRIMIDIN kinase inhibitors |
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| CA2644809A1 (en) * | 2006-03-02 | 2007-09-07 | Astellas Pharma Inc. | 17 .beta. hsd type 5 inhibitor |
| WO2009049028A1 (en) | 2007-10-09 | 2009-04-16 | Targegen Inc. | Pyrrolopyrimidine compounds and their use as janus kinase modulators |
| WO2009115084A2 (de) | 2008-03-20 | 2009-09-24 | Schebo Biotech Ag | Neue pyrrolopyrimidin-derivate und deren verwendungen |
| RU2493157C2 (ru) * | 2008-08-20 | 2013-09-20 | Пфайзер Инк. | ПРОИЗВОДНЫЕ ПИРРОЛО[2,3-d]ПИРИМИДИНА |
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