AU2015327346B2 - Boronic acid derivatives - Google Patents
Boronic acid derivatives Download PDFInfo
- Publication number
- AU2015327346B2 AU2015327346B2 AU2015327346A AU2015327346A AU2015327346B2 AU 2015327346 B2 AU2015327346 B2 AU 2015327346B2 AU 2015327346 A AU2015327346 A AU 2015327346A AU 2015327346 A AU2015327346 A AU 2015327346A AU 2015327346 B2 AU2015327346 B2 AU 2015327346B2
- Authority
- AU
- Australia
- Prior art keywords
- ethyl
- amino
- boronic acid
- acetyl
- benzofuran
- 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.)
- Ceased
Links
- 150000001642 boronic acid derivatives Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 446
- 238000011282 treatment Methods 0.000 claims abstract description 17
- 101001136986 Homo sapiens Proteasome subunit beta type-8 Proteins 0.000 claims abstract description 13
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- 208000002250 Hematologic Neoplasms Diseases 0.000 claims abstract description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
- -1 monocyclic hydrocarbon Chemical class 0.000 claims description 377
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 168
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 142
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 136
- 238000000034 method Methods 0.000 claims description 115
- 239000000203 mixture Substances 0.000 claims description 91
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 89
- 150000003839 salts Chemical class 0.000 claims description 89
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 86
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 69
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 52
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 49
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 43
- 239000012453 solvate Substances 0.000 claims description 41
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 39
- 239000004480 active ingredient Substances 0.000 claims description 31
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 30
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 22
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
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- VMWJCFLUSKZZDX-UHFFFAOYSA-N n,n-dimethylmethanamine Chemical compound [CH2]N(C)C VMWJCFLUSKZZDX-UHFFFAOYSA-N 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 15
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 13
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- 229930195733 hydrocarbon Natural products 0.000 claims description 12
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- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/69—Boron compounds
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| EP14003392 | 2014-10-01 | ||
| PCT/EP2015/002008 WO2016050359A1 (en) | 2014-10-01 | 2015-10-01 | Boronic acid derivatives |
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| AU2015327346A1 AU2015327346A1 (en) | 2017-05-18 |
| AU2015327346B2 true AU2015327346B2 (en) | 2019-12-05 |
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| AU2015327411B2 (en) | 2014-10-01 | 2020-01-02 | Merck Patent Gmbh | Boronic acid derivatives |
| CA2963198A1 (en) | 2014-10-01 | 2016-04-07 | Merck Patent Gmbh | Boronic acid derivatives |
| JP6662865B2 (ja) | 2014-10-01 | 2020-03-11 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | ボロン酸誘導体 |
| WO2019038250A1 (en) | 2017-08-24 | 2019-02-28 | Merck Patent Gmbh | Boronic acid derivatives |
| CN112469480A (zh) * | 2018-07-26 | 2021-03-09 | 默克专利股份公司 | 硼酸衍生物 |
| CN113135943A (zh) * | 2020-01-19 | 2021-07-20 | 首药控股(北京)有限公司 | 硼酸衍生物 |
| CN113135944A (zh) * | 2020-01-19 | 2021-07-20 | 首药控股(北京)有限公司 | 硼酸衍生物 |
| US20250340577A1 (en) * | 2021-03-02 | 2025-11-06 | Case Western Reserve University | Beta-lactomase inhibitors and uses thereof |
| WO2022243155A1 (en) * | 2021-05-19 | 2022-11-24 | Syngenta Crop Protection Ag | Weed control method |
| IL310390A (en) | 2021-07-29 | 2024-03-01 | Merck Patent Gmbh | Crystalline forms of [(1r)-2-(1-benzofuran-3-yl)-1-{[(1s,2r,4r)-7- oxabicyclo[2.2.1]heptan-2-yl]formamido}ethyl]boronic acid, adducts thereof, and processes to obtain |
| KR20240090392A (ko) * | 2021-10-14 | 2024-06-21 | 쇼우야오 홀딩스 (베이징) 코., 엘티디. | 보론산 유도체 |
| WO2023232830A1 (en) | 2022-06-02 | 2023-12-07 | Merck Patent Gmbh | Boronic acid adducts |
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| WO2013092979A1 (en) * | 2011-12-22 | 2013-06-27 | Ares Trading S.A. | Alpha-amino boronic acid derivatives, selective immunoproteasome inhibitors |
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| IL111175A0 (en) * | 1993-10-07 | 1994-12-29 | Du Pont Merck Pharma | Electrophilic peptide analogs as inhibitors of trypsin-like serine proteases and pharmaceutical compositions containing them |
| EP1196436A2 (en) * | 1999-07-07 | 2002-04-17 | Bristol-Myers Squibb Pharma Company | Peptide boronic acid inhibitors of hepatitis c virus protease |
| US7271186B1 (en) | 2002-12-09 | 2007-09-18 | Northwestern University | Nanomolar β-lactamase inhibitors |
| EA201000774A1 (ru) * | 2007-11-13 | 2010-12-30 | Новартис Интернэшнл Фармасьютикл Лтд. | Ингибиторы бета-лактамазы |
| AR075090A1 (es) * | 2008-09-29 | 2011-03-09 | Millennium Pharm Inc | Derivados de acido 1-amino-2-ciclobutiletilboronico inhibidores de proteosoma,utiles como agentes anticancerigenos, y composiciones farmaceuticas que los comprenden. |
| AU2015327411B2 (en) | 2014-10-01 | 2020-01-02 | Merck Patent Gmbh | Boronic acid derivatives |
| CA2963198A1 (en) | 2014-10-01 | 2016-04-07 | Merck Patent Gmbh | Boronic acid derivatives |
| JP6662865B2 (ja) | 2014-10-01 | 2020-03-11 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | ボロン酸誘導体 |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013092979A1 (en) * | 2011-12-22 | 2013-06-27 | Ares Trading S.A. | Alpha-amino boronic acid derivatives, selective immunoproteasome inhibitors |
Non-Patent Citations (1)
| Title |
|---|
| NESS STEVEN ET AL, "Structure-Based Design Guides the Improved Efficacy of Deacylation Transition State Analogue Inhibitors of TEM-1 .beta.-Lactamase", BIOCHEMISTRY, vol. 39, no. 18, pages 5312 - 5321 * |
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| JP2017536335A (ja) | 2017-12-07 |
| MX2017004046A (es) | 2017-06-19 |
| CN107001390B (zh) | 2020-11-27 |
| SG11201702623TA (en) | 2017-04-27 |
| US10294246B2 (en) | 2019-05-21 |
| CN107001390A (zh) | 2017-08-01 |
| MX370336B (es) | 2019-12-10 |
| WO2016050359A1 (en) | 2016-04-07 |
| JP6835711B2 (ja) | 2021-02-24 |
| IL251301B (en) | 2022-02-01 |
| AU2015327346A1 (en) | 2017-05-18 |
| RU2017115188A (ru) | 2018-11-06 |
| EP3201207B1 (en) | 2021-02-24 |
| BR112017006420A2 (pt) | 2017-12-19 |
| ES2873000T3 (es) | 2021-11-03 |
| RU2017115188A3 (enExample) | 2019-03-29 |
| KR20170062517A (ko) | 2017-06-07 |
| KR102450583B1 (ko) | 2022-10-04 |
| IL251301A0 (en) | 2017-05-29 |
| US20180105539A1 (en) | 2018-04-19 |
| EP3201207A1 (en) | 2017-08-09 |
| CA2963205A1 (en) | 2016-04-07 |
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