JP2014504258A5 - - Google Patents
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- JP2014504258A5 JP2014504258A5 JP2013533912A JP2013533912A JP2014504258A5 JP 2014504258 A5 JP2014504258 A5 JP 2014504258A5 JP 2013533912 A JP2013533912 A JP 2013533912A JP 2013533912 A JP2013533912 A JP 2013533912A JP 2014504258 A5 JP2014504258 A5 JP 2014504258A5
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- JP
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- carbon atoms
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- Prior art date
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 464
- 150000001875 compounds Chemical class 0.000 claims description 282
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 232
- 125000000217 alkyl group Chemical group 0.000 claims description 194
- 229910052739 hydrogen Inorganic materials 0.000 claims description 98
- 239000001257 hydrogen Substances 0.000 claims description 97
- 238000000034 method Methods 0.000 claims description 95
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 72
- 150000001721 carbon Chemical group 0.000 claims description 66
- 229910052799 carbon Inorganic materials 0.000 claims description 66
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 54
- 239000008194 pharmaceutical composition Substances 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 41
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 36
- 239000000651 prodrug Substances 0.000 claims description 31
- 229940002612 prodrug Drugs 0.000 claims description 31
- 239000012453 solvate Substances 0.000 claims description 31
- 210000004027 cell Anatomy 0.000 claims description 30
- 229910052717 sulfur Inorganic materials 0.000 claims description 29
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 239000001301 oxygen Substances 0.000 claims description 23
- 239000011593 sulfur Substances 0.000 claims description 23
- QAPXLUZMMFIIBI-UHFFFAOYSA-N 1,1,3,3-tetrafluoropropan-2-one Chemical compound FC(F)C(=O)C(F)F QAPXLUZMMFIIBI-UHFFFAOYSA-N 0.000 claims description 18
- HKIPCXRNASWFRU-UHFFFAOYSA-N 1,3-difluoropropan-2-one Chemical compound FCC(=O)CF HKIPCXRNASWFRU-UHFFFAOYSA-N 0.000 claims description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 claims description 18
- -1 monofluoromethyl Chemical group 0.000 claims description 18
- 230000003287 optical effect Effects 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 17
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 17
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 17
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 12
- 210000002540 macrophage Anatomy 0.000 claims description 12
- 150000002431 hydrogen Chemical group 0.000 claims description 11
- 102000006815 folate receptor Human genes 0.000 claims description 10
- 108020005243 folate receptor Proteins 0.000 claims description 10
- 101001116987 Homo sapiens Proton-coupled folate transporter Proteins 0.000 claims description 7
- 102000046517 human SLC46A1 Human genes 0.000 claims description 7
- 208000023275 Autoimmune disease Diseases 0.000 claims description 6
- 102100035139 Folate receptor alpha Human genes 0.000 claims description 6
- 101001023230 Homo sapiens Folate receptor alpha Proteins 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 108020003175 receptors Proteins 0.000 claims description 6
- 102000005962 receptors Human genes 0.000 claims description 6
- 230000008685 targeting Effects 0.000 claims description 6
- 102000037909 Folate transporters Human genes 0.000 claims description 5
- 108091006783 Folate transporters Proteins 0.000 claims description 5
- 108090000790 Enzymes Proteins 0.000 claims description 4
- 102000004190 Enzymes Human genes 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 150000004677 hydrates Chemical class 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
- 102000002114 Reduced Folate Carrier Human genes 0.000 claims description 2
- 108050009454 Reduced Folate Carrier Proteins 0.000 claims description 2
- 231100000433 cytotoxic Toxicity 0.000 claims description 2
- 230000001472 cytotoxic effect Effects 0.000 claims description 2
- 230000001066 destructive effect Effects 0.000 claims description 2
- 230000002757 inflammatory effect Effects 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 230000002934 lysing effect Effects 0.000 claims description 2
- 230000007524 negative regulation of DNA replication Effects 0.000 claims description 2
- 230000037361 pathway Effects 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 210000001179 synovial fluid Anatomy 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 210000001519 tissue Anatomy 0.000 claims description 2
- 208000024719 uterine cervix neoplasm Diseases 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/902,310 US20110082158A1 (en) | 2008-10-01 | 2010-10-12 | Selective proton coupled folate transporter and folate receptor, and garftase and/or other folate metabolizing enzymes inhibitor compounds and methods of using the same |
| US12/902,310 | 2010-10-12 | ||
| PCT/US2011/055584 WO2012051105A2 (en) | 2010-10-12 | 2011-10-10 | Selective proton coupled folate transporter and folate receptor, and garftase and/or other folate metabolizing enzymes inhibitor compounds and methods of using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2014504258A JP2014504258A (ja) | 2014-02-20 |
| JP2014504258A5 true JP2014504258A5 (enExample) | 2014-11-27 |
Family
ID=45938910
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013533912A Pending JP2014504258A (ja) | 2010-10-12 | 2011-10-10 | 選択的プロトン共役葉酸輸送体および葉酸受容体ならびにＧＡＲＦＴａｓｅおよび／または他の葉酸代謝酵素のインヒビター化合物、ならびにその使用方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20110082158A1 (enExample) |
| EP (1) | EP2627332A4 (enExample) |
| JP (1) | JP2014504258A (enExample) |
| CA (1) | CA2813743C (enExample) |
| WO (1) | WO2012051105A2 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016089879A1 (en) * | 2014-12-01 | 2016-06-09 | Endocyte, Inc. | Conjugates of garftase inhibitors |
| CA2964140A1 (en) * | 2014-12-02 | 2016-06-09 | Eli Lilly And Company | 1 -oxo-1,2-dihydroisoquinolin-7-yl-(5-substituted-thiophen-2-yl)-sulfonamide compounds, formulations containing those compounds, and their use as aicarft inhibitors in the treatment of cancers |
| AR103297A1 (es) | 2014-12-30 | 2017-05-03 | Forma Therapeutics Inc | Pirrolo y pirazolopirimidinas como inhibidores de la proteasa 7 específica de ubiquitina |
| MA41291A (fr) | 2014-12-30 | 2017-11-07 | Forma Therapeutics Inc | Dérivés de la pyrrolotriazinone et de l'imidazotriazinone en tant qu'inhibiteurs de la protéase spécifique de l'ubiquitine n° 7 (usp7) pour le traitement d'un cancer |
| JP2018504431A (ja) | 2015-02-05 | 2018-02-15 | フォーマ セラピューティクス，インコーポレイテッド | ユビキチン特異的プロテアーゼ７阻害物質としてのチエノピリミジノン |
| JP2018504430A (ja) | 2015-02-05 | 2018-02-15 | フォーマ セラピューティクス，インコーポレイテッド | ユビキチン特異的プロテアーゼ７阻害物質としてのキナゾリノン及びアザキナゾリノン |
| HK1248221A1 (zh) | 2015-02-05 | 2018-10-12 | Forma Therapeutics, Inc. | 异噻唑啉酮类，吡唑并嘧啶酮类和吡咯并嘧啶酮作为泛蛋白特异性蛋白酶7抑制剂 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991000092A1 (en) * | 1989-06-13 | 1991-01-10 | Smithkline Beecham Corporation | Inhibition of interleukin-1 and tumor necrosis factor production by monocytes and/or macrophages |
| JPH03173890A (ja) * | 1989-09-21 | 1991-07-29 | Takeda Chem Ind Ltd | ピロロ［２，３―ｄ］ピリミジン誘導体，その製造法，用途及び中間体 |
| US5248775A (en) * | 1989-12-11 | 1993-09-28 | The Trustees Of Princeton University | Pyrrolo(2,3-d)pyrimidines |
| US4996206A (en) * | 1989-12-11 | 1991-02-26 | The Trustees Of Princeton University | N-(pyrrolo[2,3-d]pyrimidin-3-ylacyl)-glutamic acid derivatives |
| JPH04117381A (ja) * | 1989-12-20 | 1992-04-17 | Takeda Chem Ind Ltd | 縮合複素環化合物，その製造法，用途及び中間体 |
| EP0438261A3 (en) * | 1990-01-16 | 1992-02-26 | Takeda Chemical Industries, Ltd. | Condensed heterocyclic glutamic acid derivatives, their production and use |
| JPH0578362A (ja) * | 1990-01-16 | 1993-03-30 | Takeda Chem Ind Ltd | 縮合複素環化合物，その製造法，用途及び中間体 |
| US5939420A (en) * | 1991-04-08 | 1999-08-17 | Duquesne University Of The Holy Ghost | Pyrrolo 2,3d!derivatives |
| JP3144903B2 (ja) * | 1991-08-21 | 2001-03-12 | エーザイ株式会社 | 縮合ピリミジン誘導体 |
| JPH06172358A (ja) * | 1991-12-27 | 1994-06-21 | Takeda Chem Ind Ltd | 縮合ピリミジン誘導体、その製造法および用途 |
| EP0923287A4 (en) * | 1996-08-30 | 2001-08-01 | Lilly Co Eli | NON-CLASSIC PYRROLO (2,3-D) PYRIMIDINE ANTIFOLATE |
| WO2000013688A1 (en) * | 1998-09-04 | 2000-03-16 | Agouron Pharmaceuticals, Inc. | Compounds useful as aicarft inhibitors |
| EP1424336A4 (en) * | 2001-09-03 | 2004-11-10 | Takeda Chemical Industries Ltd | 1,3-BENZOTHIAZINE DERIVATIVES AND THEIR USE |
| AU2003258061A1 (en) * | 2002-08-02 | 2004-02-23 | Salmedix, Inc. | Therapeutic inhibitionof protein kinases in cancer cells |
| US20050165029A1 (en) * | 2004-01-13 | 2005-07-28 | Ambit Biosciences Corporation | Pyrrolopyrimidine derivatives and analogs and their use in the treatment and prevention of diseases |
| US8030319B2 (en) * | 2005-02-10 | 2011-10-04 | Duquesne University Of The Holy Ghost | Methods for treating cancer and other pathological proliferating disorders by inhibiting mitosis using pyrrolo[2 3-d]pyrimidines |
| CN101195625A (zh) * | 2007-12-06 | 2008-06-11 | 上海交通大学 | 用于抗肿瘤药物抗叶酸剂及其盐和中间体 |
| US8252804B2 (en) * | 2008-10-01 | 2012-08-28 | Duquesne University Of The Holy Spirit | Selective proton coupled folate transporter and folate receptor, and GARFTase inhibitor compounds and methods of using the same |
-
2010
- 2010-10-12 US US12/902,310 patent/US20110082158A1/en not_active Abandoned
-
2011
- 2011-10-10 CA CA2813743A patent/CA2813743C/en active Active
- 2011-10-10 EP EP11833198.2A patent/EP2627332A4/en not_active Withdrawn
- 2011-10-10 JP JP2013533912A patent/JP2014504258A/ja active Pending
- 2011-10-10 WO PCT/US2011/055584 patent/WO2012051105A2/en not_active Ceased
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