JP2013542223A5 - - Google Patents
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- Publication number
- JP2013542223A5 JP2013542223A5 JP2013536669A JP2013536669A JP2013542223A5 JP 2013542223 A5 JP2013542223 A5 JP 2013542223A5 JP 2013536669 A JP2013536669 A JP 2013536669A JP 2013536669 A JP2013536669 A JP 2013536669A JP 2013542223 A5 JP2013542223 A5 JP 2013542223A5
- Authority
- JP
- Japan
- Prior art keywords
- alkylene
- aryl
- alkyl
- group
- branched
- 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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- 125000000217 alkyl group Chemical group 0.000 claims description 146
- 125000002947 alkylene group Chemical group 0.000 claims description 124
- 125000003118 aryl group Chemical group 0.000 claims description 120
- 150000001875 compounds Chemical class 0.000 claims description 54
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 52
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 47
- 125000001072 heteroaryl group Chemical group 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 27
- 229920006395 saturated elastomer Polymers 0.000 claims description 26
- 201000010099 disease Diseases 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 239000000651 prodrug Substances 0.000 claims description 18
- 229940002612 prodrug Drugs 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 102000004452 Arginase Human genes 0.000 claims description 16
- 108700024123 Arginases Proteins 0.000 claims description 16
- 102100030356 Arginase-2, mitochondrial Human genes 0.000 claims description 14
- 101710186578 Arginase-2, mitochondrial Proteins 0.000 claims description 14
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 13
- 125000004450 alkenylene group Chemical group 0.000 claims description 13
- 125000004419 alkynylene group Chemical group 0.000 claims description 13
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 13
- 125000000732 arylene group Chemical group 0.000 claims description 13
- 125000004104 aryloxy group Chemical group 0.000 claims description 13
- 229910052796 boron Inorganic materials 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 230000000694 effects Effects 0.000 claims description 12
- 125000004043 oxo group Chemical group O=* 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- 230000002265 prevention Effects 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 210000004027 cell Anatomy 0.000 claims description 6
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 5
- 201000001881 impotence Diseases 0.000 claims description 5
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- BXGZDYTYKYZJJN-UHFFFAOYSA-N 1-amino-2-(3-boronopropyl)cyclohexane-1-carboxylic acid Chemical compound OC(=O)C1(N)CCCCC1CCCB(O)O BXGZDYTYKYZJJN-UHFFFAOYSA-N 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 206010016654 Fibrosis Diseases 0.000 claims description 2
- 206010020772 Hypertension Diseases 0.000 claims description 2
- 206010063837 Reperfusion injury Diseases 0.000 claims description 2
- 210000001744 T-lymphocyte Anatomy 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 230000004064 dysfunction Effects 0.000 claims description 2
- 230000004761 fibrosis Effects 0.000 claims description 2
- 208000012947 ischemia reperfusion injury Diseases 0.000 claims description 2
- 208000017169 kidney disease Diseases 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 230000029663 wound healing Effects 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 9
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 description 12
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 125000001188 haloalkyl group Chemical group 0.000 description 6
- 241000124008 Mammalia Species 0.000 description 3
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 2
- 238000003419 tautomerization reaction Methods 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000938605 Crocodylia Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000283903 Ovis aries Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40676010P | 2010-10-26 | 2010-10-26 | |
| US61/406,760 | 2010-10-26 | ||
| PCT/US2011/056844 WO2012058065A1 (en) | 2010-10-26 | 2011-10-19 | Boronates as arginase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013542223A JP2013542223A (ja) | 2013-11-21 |
| JP2013542223A5 true JP2013542223A5 (enExample) | 2014-12-04 |
| JP5909239B2 JP5909239B2 (ja) | 2016-04-26 |
Family
ID=44913403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013536669A Active JP5909239B2 (ja) | 2010-10-26 | 2011-10-19 | アルギナーゼ阻害剤としてのボロネート |
Country Status (19)
| Country | Link |
|---|---|
| US (5) | US9233985B2 (enExample) |
| EP (3) | EP3034509B1 (enExample) |
| JP (1) | JP5909239B2 (enExample) |
| CN (2) | CN103249737B (enExample) |
| AU (1) | AU2011320732B2 (enExample) |
| BR (1) | BR112013010099B1 (enExample) |
| CA (1) | CA2815536C (enExample) |
| DK (1) | DK2632927T3 (enExample) |
| ES (2) | ES2568680T3 (enExample) |
| HK (1) | HK1223104A1 (enExample) |
| HR (1) | HRP20160305T1 (enExample) |
| HU (1) | HUE027317T2 (enExample) |
| IL (1) | IL225926A (enExample) |
| MX (1) | MX336381B (enExample) |
| PL (1) | PL2632927T3 (enExample) |
| RS (1) | RS54750B1 (enExample) |
| SI (1) | SI2632927T1 (enExample) |
| SM (1) | SMT201600141B (enExample) |
| WO (1) | WO2012058065A1 (enExample) |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX348422B (es) | 2010-04-22 | 2017-06-12 | Mars Inc | Inhibidores de arginasa y sus aplicaciones terapeuticas. |
| EP2603514B1 (en) | 2010-08-10 | 2018-07-18 | Rempex Pharmaceuticals, Inc. | Cyclic boronic acid ester derivatives and therapeutic uses thereof |
| DK2632927T3 (en) | 2010-10-26 | 2016-04-11 | Mars Inc | Boronates AS ARGINSASEINHIBITORER |
| CA2870526C (en) * | 2012-04-18 | 2020-05-05 | Mars, Incorporated | Ring constrained analogs as arginase inhibitors |
| JP2016509594A (ja) | 2013-01-04 | 2016-03-31 | レンペックス・ファーマシューティカルズ・インコーポレイテッド | ボロン酸誘導体及びその治療的使用 |
| US11624093B2 (en) | 2014-04-24 | 2023-04-11 | Dana-Farber Cancer Institute, Inc. | Tumor suppressor and oncogene biomarkers predictive of anti-immune checkpoint inhibitor response |
| US9687497B1 (en) | 2014-05-05 | 2017-06-27 | Rempex Pharmaceuticals, Inc. | Salts and polymorphs of cyclic boronic acid ester derivatives and therapeutic uses thereof |
| RS59488B1 (sr) | 2014-05-05 | 2019-12-31 | Rempex Pharmaceuticals Inc | Sinteza boronatnih soli i njihove upotrebe |
| MX2016015093A (es) | 2014-05-19 | 2017-03-27 | Rempex Pharmaceuticals Inc | Derivados de acido boronico y sus usos terapeuticos. |
| EA201692301A1 (ru) | 2014-07-01 | 2017-06-30 | Ремпекс Фармасьютикалз, Инк. | Производные бороновой кислоты и их терапевтическое применение |
| US10662205B2 (en) | 2014-11-18 | 2020-05-26 | Qpex Biopharma, Inc. | Cyclic boronic acid ester derivatives and therapeutic uses thereof |
| PL410665A1 (pl) | 2014-12-29 | 2016-07-04 | Oncoarendi Therapeutics Spółka Z Ograniczoną Odpowiedzialnością | Inhibitory arginazy oraz ich zastosowania terapeutyczne |
| US20180051041A1 (en) | 2015-03-17 | 2018-02-22 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| US10143699B2 (en) | 2015-06-23 | 2018-12-04 | Calithera Biosciences, Inc. | Compositions and methods for inhibiting arginase activity |
| SG10201912736UA (en) | 2015-10-01 | 2020-02-27 | Potenza Therapeutics Inc | Anti-tigit antigen-binding proteins and methods of use thereof |
| US10065974B2 (en) * | 2015-10-30 | 2018-09-04 | Calithera Biosciences, Inc. | Compositions and methods for inhibiting arginase activity |
| PL417066A1 (pl) * | 2016-05-04 | 2017-11-06 | Oncoarendi Therapeutics Spółka Z Ograniczoną Odpowiedzialnością | Inhibitory arginazy oraz ich zastosowania terapeutyczne |
| EP3478693B1 (en) | 2016-06-30 | 2021-07-21 | Qpex Biopharma, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| EP3538111B1 (en) * | 2016-11-08 | 2022-01-19 | Calithera Biosciences, Inc. | Arginase inhibitor combination therapies |
| ES2970715T3 (es) * | 2016-12-22 | 2024-05-30 | Prec Pharmaceuticals Inc | Composiciones y métodos para inhibir la actividad de la arginasa |
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| AU2018265873A1 (en) | 2017-05-12 | 2019-11-28 | Calithera Biosciences, Inc. | Method of preparing (3R,4S)-3-acetamido-4-allyl-N-(tert-butyl)pyrrolidine-3-carboxamide |
| JP7377545B2 (ja) | 2017-10-11 | 2023-11-10 | キューペックス バイオファーマ， インコーポレイテッド | ボロン酸誘導体およびその合成 |
| CN111491937A (zh) * | 2017-12-22 | 2020-08-04 | 广东新契生物医药科技有限公司 | 作为精氨酸酶抑制剂的杂环化合物 |
| CR20200418A (es) | 2018-02-17 | 2020-10-27 | Astrazeneca Ab | Inhibidores de orginasa y sus mètodos de uso antecedentes |
| KR102656571B1 (ko) * | 2018-03-05 | 2024-04-11 | 아르커스 바이오사이언시즈 인코포레이티드 | 아르기나아제 억제제 |
| US12215116B2 (en) * | 2018-03-13 | 2025-02-04 | Merck Sharp & Dohme Llc | Arginase inhibitors and methods of use |
| PL3774843T3 (pl) * | 2018-03-29 | 2022-11-14 | Molecure Sa | Dipeptydowe pochodne piperydyny |
| CA3097127A1 (en) | 2018-04-20 | 2019-10-24 | Qpex Biopharma, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| CN111770756B (zh) * | 2018-04-27 | 2023-03-31 | 四川科伦博泰生物医药股份有限公司 | 非天然氨基酸类衍生物、包含其的药物组合物及其制备方法和用途 |
| WO2019218904A1 (zh) * | 2018-05-18 | 2019-11-21 | 四川科伦博泰生物医药股份有限公司 | 非天然氨基酸类衍生物、其制备方法及用途 |
| WO2019245890A1 (en) | 2018-06-20 | 2019-12-26 | Merck Sharp & Dohme Corp. | Arginase inhibitors and methods of use |
| WO2020102646A2 (en) * | 2018-11-16 | 2020-05-22 | Arcus Biosciences, Inc. | Inhibitors of arg1 and/or arg2 |
| US11034669B2 (en) | 2018-11-30 | 2021-06-15 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| US12240867B2 (en) | 2018-12-18 | 2025-03-04 | Merck Sharp & Dohme Llc | Arginase inhibitors and methods of use |
| EP3917936A4 (en) * | 2019-02-06 | 2022-12-14 | Guangdong Newopp Biopharmaceuticals Co., Ltd. | ALKYBORONIC ACIDS AS ARGINASE INHIBITORS |
| PT3921033T (pt) | 2019-02-08 | 2023-10-11 | Astrazeneca Ab | Inibidores de arginase e métodos de utilização dos mesmos |
| AU2020319132B2 (en) * | 2019-07-23 | 2023-09-07 | Astrazeneca Ab | Arginase inhibitors and methods of use thereof |
| CN110734456A (zh) * | 2019-11-06 | 2020-01-31 | 南京谷睿生物科技有限公司 | 一种化合物及其制备方法和医药上的应用 |
| EP4087583A4 (en) * | 2020-01-07 | 2024-01-24 | Merck Sharp & Dohme LLC | Arginase inhibitors and methods of use |
| WO2021257863A1 (en) | 2020-06-19 | 2021-12-23 | Incyte Corporation | Pyrrolotriazine compounds as jak2 v617f inhibitors |
| WO2021257857A1 (en) | 2020-06-19 | 2021-12-23 | Incyte Corporation | Naphthyridinone compounds as jak2 v617f inhibitors |
| US11767323B2 (en) | 2020-07-02 | 2023-09-26 | Incyte Corporation | Tricyclic pyridone compounds as JAK2 V617F inhibitors |
| WO2022006457A1 (en) | 2020-07-02 | 2022-01-06 | Incyte Corporation | Tricyclic urea compounds as jak2 v617f inhibitors |
| WO2022046989A1 (en) | 2020-08-27 | 2022-03-03 | Incyte Corporation | Tricyclic urea compounds as jak2 v617f inhibitors |
| US11919908B2 (en) | 2020-12-21 | 2024-03-05 | Incyte Corporation | Substituted pyrrolo[2,3-d]pyrimidine compounds as JAK2 V617F inhibitors |
| TW202228720A (zh) | 2020-12-22 | 2022-08-01 | 波蘭商昂科艾倫迪治療法股份公司 | 精胺酸酶抑制劑及其使用方法 |
| WO2022182839A1 (en) | 2021-02-25 | 2022-09-01 | Incyte Corporation | Spirocyclic lactams as jak2 v617f inhibitors |
| WO2023283332A1 (en) * | 2021-07-07 | 2023-01-12 | Emory University | Uses of arginase inhibitors for managing kidney disease and cardiovascular conditions |
| US20250099408A1 (en) | 2022-01-21 | 2025-03-27 | Sammy Oyoo OPIYO | Improved suramin methods and compositions |
| JP2025509672A (ja) | 2022-03-17 | 2025-04-11 | インサイト・コーポレイション | Ｊａｋ２ ｖ６１７ｆ阻害剤としての三環式尿素化合物 |
| US20240190876A1 (en) | 2022-10-21 | 2024-06-13 | Incyte Corporation | Tricyclic Urea Compounds As JAK2 V617F Inhibitors |
| CN121079299A (zh) | 2023-03-13 | 2025-12-05 | 因赛特公司 | 作为激酶抑制剂的双环脲 |
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| PL417066A1 (pl) | 2016-05-04 | 2017-11-06 | Oncoarendi Therapeutics Spółka Z Ograniczoną Odpowiedzialnością | Inhibitory arginazy oraz ich zastosowania terapeutyczne |
| ES2970715T3 (es) | 2016-12-22 | 2024-05-30 | Prec Pharmaceuticals Inc | Composiciones y métodos para inhibir la actividad de la arginasa |
| AU2018265873A1 (en) | 2017-05-12 | 2019-11-28 | Calithera Biosciences, Inc. | Method of preparing (3R,4S)-3-acetamido-4-allyl-N-(tert-butyl)pyrrolidine-3-carboxamide |
-
2011
- 2011-10-19 DK DK11779904.9T patent/DK2632927T3/en active
- 2011-10-19 HU HUE11779904A patent/HUE027317T2/en unknown
- 2011-10-19 MX MX2013004491A patent/MX336381B/es unknown
- 2011-10-19 EP EP16150285.1A patent/EP3034509B1/en active Active
- 2011-10-19 RS RS20160243A patent/RS54750B1/sr unknown
- 2011-10-19 JP JP2013536669A patent/JP5909239B2/ja active Active
- 2011-10-19 EP EP20162218.0A patent/EP3719024A1/en active Pending
- 2011-10-19 BR BR112013010099-0A patent/BR112013010099B1/pt not_active IP Right Cessation
- 2011-10-19 WO PCT/US2011/056844 patent/WO2012058065A1/en not_active Ceased
- 2011-10-19 EP EP11779904.9A patent/EP2632927B1/en active Active
- 2011-10-19 CN CN201180057717.4A patent/CN103249737B/zh not_active Expired - Fee Related
- 2011-10-19 AU AU2011320732A patent/AU2011320732B2/en not_active Ceased
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