SA518400742B1 - مشتقات حمض بورونيك واستخداماتها العلاجية - Google Patents
مشتقات حمض بورونيك واستخداماتها العلاجية Download PDFInfo
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- SA518400742B1 SA518400742B1 SA518400742A SA518400742A SA518400742B1 SA 518400742 B1 SA518400742 B1 SA 518400742B1 SA 518400742 A SA518400742 A SA 518400742A SA 518400742 A SA518400742 A SA 518400742A SA 518400742 B1 SA518400742 B1 SA 518400742B1
- Authority
- SA
- Saudi Arabia
- Prior art keywords
- alkyl
- atoms
- compound
- group
- aryl
- Prior art date
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- 150000001642 boronic acid derivatives Chemical class 0.000 title abstract description 4
- 230000001225 therapeutic effect Effects 0.000 title description 6
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- -1 for example Substances 0.000 claims abstract description 105
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- 125000004429 atom Chemical group 0.000 claims description 150
- 125000003118 aryl group Chemical group 0.000 claims description 101
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 69
- 125000003545 alkoxy group Chemical group 0.000 claims description 64
- 125000004122 cyclic group Chemical group 0.000 claims description 61
- 229910052736 halogen Inorganic materials 0.000 claims description 58
- 150000003839 salts Chemical class 0.000 claims description 58
- 125000000623 heterocyclic group Chemical group 0.000 claims description 50
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- 125000001424 substituent group Chemical group 0.000 claims description 36
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- 239000001257 hydrogen Substances 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 125000003342 alkenyl group Chemical group 0.000 claims description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
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- 229940079593 drug Drugs 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
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- 238000013461 design Methods 0.000 claims description 4
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- UNJFKXSSGBWRBZ-BJCIPQKHSA-N ceftibuten Chemical group S1C(N)=NC(C(=C\CC(O)=O)\C(=O)N[C@@H]2C(N3C(=CCS[C@@H]32)C(O)=O)=O)=C1 UNJFKXSSGBWRBZ-BJCIPQKHSA-N 0.000 claims description 3
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- 241000405961 Scomberomorus regalis Species 0.000 claims 1
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- 108020004999 messenger RNA Proteins 0.000 claims 1
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- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 42
- 239000003208 petroleum Substances 0.000 description 39
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
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- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 30
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- 125000002947 alkylene group Chemical group 0.000 description 28
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- WZPBZJONDBGPKJ-VEHQQRBSSA-N aztreonam Chemical compound O=C1N(S([O-])(=O)=O)[C@@H](C)[C@@H]1NC(=O)C(=N/OC(C)(C)C(O)=O)\C1=CSC([NH3+])=N1 WZPBZJONDBGPKJ-VEHQQRBSSA-N 0.000 description 25
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- 238000011282 treatment Methods 0.000 description 23
- 238000003818 flash chromatography Methods 0.000 description 22
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 22
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- WZPBZJONDBGPKJ-UHFFFAOYSA-N Antibiotic SQ 26917 Natural products O=C1N(S(O)(=O)=O)C(C)C1NC(=O)C(=NOC(C)(C)C(O)=O)C1=CSC(N)=N1 WZPBZJONDBGPKJ-UHFFFAOYSA-N 0.000 description 14
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- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 14
- 239000011575 calcium Substances 0.000 description 13
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- DMJNNHOOLUXYBV-PQTSNVLCSA-N meropenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)S[C@@H]1CN[C@H](C(=O)N(C)C)C1 DMJNNHOOLUXYBV-PQTSNVLCSA-N 0.000 description 13
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
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- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 150000003512 tertiary amines Chemical class 0.000 description 1
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- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
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- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
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- VAMSVIZLXJOLHZ-QWFSEIHXSA-N tigemonam Chemical compound O=C1N(OS(O)(=O)=O)C(C)(C)[C@@H]1NC(=O)C(=N/OCC(O)=O)\C1=CSC(N)=N1 VAMSVIZLXJOLHZ-QWFSEIHXSA-N 0.000 description 1
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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
- C07F5/05—Cyclic compounds having at least one ring containing boron but no carbon in the ring
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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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
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- A—HUMAN NECESSITIES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
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- A—HUMAN NECESSITIES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
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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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
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| US201662357165P | 2016-06-30 | 2016-06-30 | |
| PCT/US2017/039787 WO2018005662A1 (en) | 2016-06-30 | 2017-06-28 | Boronic acid derivatives and therapeutic uses thereof |
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| RS60310B1 (sr) | 2010-08-10 | 2020-07-31 | Rempex Pharmaceuticals Inc | Ciklični derivati estra boronske kiseline, postupak za pripremu injihove terapeutske upotrebe |
| EP2943204B1 (en) | 2013-01-10 | 2019-03-13 | Venatorx Pharmaceuticals Inc | Beta-lactamase inhibitors |
| PT3154989T (pt) | 2014-06-11 | 2021-05-18 | Venatorx Pharmaceuticals Inc | Inibidores de beta-lactamase |
| WO2016081297A1 (en) | 2014-11-18 | 2016-05-26 | Rempex Pharmaceuticals, Inc. | Cyclic boronic acid ester derivatives and therapeutic uses thereof |
| US20180051041A1 (en) | 2015-03-17 | 2018-02-22 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| CN108472284A (zh) | 2015-09-11 | 2018-08-31 | 维纳拓尔斯制药公司 | β-内酰胺酶抑制剂 |
| ES2894251T3 (es) * | 2016-06-30 | 2022-02-14 | Qpex Biopharma Inc | Derivados de ácido borónico y usos terapéuticos de los mismos |
| JOP20190188A1 (ar) | 2017-02-01 | 2019-08-01 | Rempex Pharmaceuticals Inc | جهاز وعملية تدفق مستمرة لإنتاج مشتق حمض بورونيك |
| MA47743A (fr) | 2017-03-06 | 2020-01-15 | Venatorx Pharmaceuticals Inc | Formes solides et compositions de combinaison comprenant un inhibiteur de bêta-lactamase et leurs utilisations |
| EP3630783A4 (en) | 2017-05-26 | 2021-03-03 | Venatorx Pharmaceuticals, Inc. | PENICILLIN-BINDING PROTEIN INHIBITORS |
| US11332485B2 (en) | 2017-05-26 | 2022-05-17 | VenatoRx Pharmaceuticals, Inc. | Penicillin-binding protein inhibitors |
| MX2020003495A (es) * | 2017-10-11 | 2020-09-18 | Qpex Biopharma Inc | Derivados de acido boronico y sintesis de los mismos. |
| US12016868B2 (en) * | 2018-04-20 | 2024-06-25 | Qpex Biopharma, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| EP3802551A4 (en) | 2018-05-25 | 2022-03-02 | Venatorx Pharmaceuticals, Inc. | Penicillin-binding protein inhibitors |
| CN113382713A (zh) * | 2018-11-29 | 2021-09-10 | 维纳拓尔斯制药公司 | 包含β-内酰胺酶抑制剂的组合式组合物及其用途 |
| PL3986419T3 (pl) | 2019-06-19 | 2025-09-08 | Qpex Biopharma, Inc. | Pochodne kwasu boronowego i ich zastosowania terapeutyczne |
| TW202123945A (zh) * | 2019-09-13 | 2021-07-01 | 日商鹽野義製藥股份有限公司 | 具有抗菌作用的醫藥組成物 |
| EP4049680A4 (en) * | 2019-10-25 | 2024-01-10 | Sumitomo Pharma Co., Ltd. | NEW SUBSTITUTED CONDENSED RING CONNECTION |
| WO2021188700A1 (en) * | 2020-03-18 | 2021-09-23 | Qpex Biopharma, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| BR112022022367A2 (pt) | 2020-05-05 | 2023-01-10 | Qpex Biopharma Inc | Derivados e síntese de ácido borônico, formas polimórficas e usos terapêuticos dos mesmos |
| JP2023538645A (ja) * | 2020-08-20 | 2023-09-08 | フェーノ・セラピューティクス・カンパニー・リミテッド | ボロン酸化合物 |
| EP4319760A4 (en) * | 2021-04-05 | 2025-01-08 | Qpex Biopharma, Inc. | CEFTIBUTENE DOSAGE REGIMEN |
| JP2024514055A (ja) | 2021-04-13 | 2024-03-28 | 上海拓界生物医薬科技有限公司 | β－ラクタマーゼ阻害剤としてのホウ酸誘導体 |
| CN113150022B (zh) * | 2021-04-23 | 2022-12-06 | 四川大学 | 3-取代五元环状硼酸酯衍生物及其药物组合物和制药用途 |
| WO2023066292A1 (zh) * | 2021-10-19 | 2023-04-27 | 上海济煜医药科技有限公司 | 三环类硼酸衍生物及其制备方法和应用 |
| WO2023155869A1 (zh) * | 2022-02-18 | 2023-08-24 | 辉诺生物医药科技（杭州）有限公司 | 新的硼酸类化合物的晶型及其制备方法 |
| CN114716465B (zh) * | 2022-05-06 | 2024-05-24 | 上海中医药大学 | 一种双环硼酸酯类化合物的制备方法及其应用 |
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| WO2025111328A1 (en) | 2023-11-21 | 2025-05-30 | VenatoRx Pharmaceuticals, Inc. | Citrate coordination complex of an orally-delivered beta-lactamase inhibitor and uses thereof |
| WO2025119216A1 (zh) * | 2023-12-04 | 2025-06-12 | 珠海联邦制药股份有限公司 | 硼酸类β-内酰胺酶抑制剂及其制备方法和应用 |
| WO2026067428A1 (zh) * | 2024-09-30 | 2026-04-02 | 科睿迪(南京)医药科技有限公司 | 硼酸衍生物及其制备方法和应用 |
Family Cites Families (126)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3686398A (en) * | 1970-07-20 | 1972-08-22 | Chevron Res | 10,9-boroxarophenanthrene as fungicides |
| US4194047A (en) | 1975-11-21 | 1980-03-18 | Merck & Co., Inc. | Substituted N-methylene derivatives of thienamycin |
| US4260543A (en) | 1978-07-03 | 1981-04-07 | Merck & Co., Inc. | Crystalline N-formimidoyl thienamycin |
| US4409214A (en) | 1979-11-19 | 1983-10-11 | Fujisawa Pharmaceutical, Co., Ltd. | 7-Acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof |
| US4353807A (en) | 1981-03-24 | 1982-10-12 | Mobil Oil Corporation | Lubricants and fuels containing boroxarophenanthrene compounds |
| FR2573070B1 (fr) | 1984-11-13 | 1987-01-30 | Rhone Poulenc Sante | Procede de preparation de composes carbonyles |
| US4783443A (en) | 1986-03-03 | 1988-11-08 | The University Of Chicago | Amino acyl cephalosporin derivatives |
| CA1283404C (en) | 1986-07-01 | 1991-04-23 | Shigeru Sanai | Cephalosporin compounds, processes for their preparation and antibacterial agents |
| NZ220764A (en) | 1986-07-02 | 1989-09-27 | Shionogi & Co | Crystalline form of 7beta((z)-2-(2-aminothiazol-4-yl)-4- carboxybut-2-enoylamino)-3-cephem-4-carboxylic acid and pharmaceutical compositions |
| ZA893284B (en) | 1988-05-04 | 1990-03-28 | Igen Inc | Peptide analogs and their use as haptens to elicit catalytic antibodies |
| US5442100A (en) | 1992-08-14 | 1995-08-15 | The Procter & Gamble Company | β-aminoalkyl and β-N-peptidylaminoalkyl boronic acids |
| US5888998A (en) | 1997-04-24 | 1999-03-30 | Synphar Laboratories, Inc. | 2-oxo-1-azetidine sulfonic acid derivatives as potent β-lactamase inhibitors |
| AU8140898A (en) | 1997-06-13 | 1998-12-30 | Northwestern University | Inhibitors of beta-lactamases and uses therefor |
| US6184363B1 (en) | 1997-06-13 | 2001-02-06 | Northwestern University | Inhibitors of β-lactamases and uses therefor |
| WO2000035904A1 (en) | 1998-12-16 | 2000-06-22 | Northwestern University | INHIBITORS OF β-LACTAMASES AND USES THEREFOR |
| AU2190400A (en) | 1998-12-16 | 2000-07-03 | Northwestern University | Inhibitors of beta-lactamases and uses therefor |
| TR200200795T2 (tr) | 1999-09-25 | 2002-07-22 | Smithkline Beecham P. L. C. | 5-HT1B antagonistleri olarak piperazin türevleri |
| JP2003513890A (ja) | 1999-10-28 | 2003-04-15 | メルク エンド カムパニー インコーポレーテッド | 新規なコハク酸系メタロ−β−ラクタマーゼ阻害薬およびそれの細菌感染治療での使用 |
| WO2002022137A1 (en) | 2000-09-12 | 2002-03-21 | Shoichet Brian K | β-LACTAM ANALOGS AND USES THEREFOR |
| ATE298750T1 (de) | 2000-09-14 | 2005-07-15 | Pantherix Ltd | 3-(heteroarylacetamido)-2-oxo-azetidin-1- sulfonsäure derivate als antibakterielle mittel |
| AU2002243508A1 (en) | 2001-01-10 | 2002-07-24 | Bristol-Myers Squibb Company Patent Department | Alpha-aminoboronic acids prepared by novel synthetic methods |
| DE10118698A1 (de) | 2001-04-17 | 2002-11-07 | Jerini Ag | Verfahren zur Immobilisierung und damit hergestellte Anordnungen von Verbindungen auf einer planaren Oberfläche |
| AU2002360732A1 (en) * | 2001-12-26 | 2003-07-24 | Guilford Pharmaceuticals | Change inhibitors of dipeptidyl peptidase iv |
| FR2835186B1 (fr) | 2002-01-28 | 2006-10-20 | Aventis Pharma Sa | Nouveaux composes heterocycliques, actifs comme inhibiteurs de beta-lactamases |
| JP2003229277A (ja) | 2002-02-04 | 2003-08-15 | Matsushita Electric Ind Co Ltd | 発光素子材料およびそれを用いた発光素子並びに装置 |
| AUPS065102A0 (en) | 2002-02-20 | 2002-03-14 | Unisearch Limited | Fluorous acetalation |
| AU2003261974A1 (en) | 2002-09-11 | 2004-04-30 | Kureha Chemical Industry Company, Limited | Amine compounds and use thereof |
| AU2003268752A1 (en) | 2002-10-30 | 2004-05-25 | Sumitomo Chemical Company, Limited | High-molecular compounds and polymerer light emitting devices made by using the same |
| US7439253B2 (en) | 2002-12-06 | 2008-10-21 | Novexel | Heterocyclic compounds, their preparation and their use as medicaments, in particular as antibacterials and beta-lactamase inhibitors |
| US7271186B1 (en) | 2002-12-09 | 2007-09-18 | Northwestern University | Nanomolar β-lactamase inhibitors |
| MXPA05006798A (es) | 2002-12-20 | 2006-03-09 | Migenix Corp | Ligandos de adenina nucleotido translocasa (ant) y composiciones y metodos relacionados a estos. |
| TW200418791A (en) | 2003-01-23 | 2004-10-01 | Bristol Myers Squibb Co | Pharmaceutical compositions for inhibiting proteasome |
| JP4233365B2 (ja) | 2003-03-25 | 2009-03-04 | 三井化学株式会社 | アザジオール錯体化合物、及び該化合物を用いる光記録媒体 |
| US7842941B2 (en) | 2003-10-06 | 2010-11-30 | Sumitomo Chemical Company, Limited | Aromatic compound |
| BRPI0415185A (pt) | 2003-10-10 | 2006-11-28 | Pfizer Prod Inc | 2h-[1,2,4]triazol[4,3-a]pirazinas substituìdas como inibidores da gsk-3 |
| SG134333A1 (en) * | 2003-11-12 | 2007-08-29 | Phenomix Corp | Heterocyclic boronic acid compounds |
| TW200600494A (en) | 2004-03-08 | 2006-01-01 | Chugai Pharmaceutical Co Ltd | Bisphenyl compounds useful as vitamin d3 receptor agonists |
| US20060019116A1 (en) | 2004-07-22 | 2006-01-26 | Eastman Kodak Company | White electroluminescent device with anthracene derivative host |
| TW200618820A (en) | 2004-11-05 | 2006-06-16 | Alza Corp | Liposome formulations of boronic acid compounds |
| US20060178357A1 (en) | 2005-02-10 | 2006-08-10 | Buynak John D | Chphalosporin-derived mercaptans as inhibitors of serine and metallo-beta-lactamases |
| EP2343304B1 (en) | 2005-02-16 | 2015-06-10 | Anacor Pharmaceuticals, Inc. | Biocidal boronophthalide compounds |
| US7612203B2 (en) | 2005-02-22 | 2009-11-03 | Teva Pharmaceutical Industries Ltd. | Rosuvastatin and salts thereof free of rosuvastatin alkylether and a process for the preparation thereof |
| WO2006101779A2 (en) | 2005-03-15 | 2006-09-28 | The University Of Chicago | Non-aqueous electrolytes for lithium ion batteries |
| US7825139B2 (en) * | 2005-05-25 | 2010-11-02 | Forest Laboratories Holdings Limited (BM) | Compounds and methods for selective inhibition of dipeptidyl peptidase-IV |
| TW200734311A (en) | 2005-11-21 | 2007-09-16 | Astrazeneca Ab | New compounds |
| CA2783572C (en) | 2005-12-07 | 2016-08-09 | Basilea Pharmaceutica Ag | Useful combinations of monobactam antibiotics with beta-lactamase inhibitors |
| PT1988779E (pt) | 2006-02-16 | 2015-09-04 | Anacor Pharmaceuticals Inc | Moléculas pequenas contendo boro como agentes antiinflamatórios |
| AU2007300531A1 (en) | 2006-09-27 | 2008-04-03 | Merck Sharp & Dohme Corp. | Novel inhibitors of beta-lactamase |
| RU2488394C2 (ru) | 2007-03-23 | 2013-07-27 | Базилеа Фармацойтика Аг | Комбинированные лекарственные средства для лечения бактериальных инфекций |
| EP2181103B1 (en) * | 2007-07-23 | 2015-08-05 | The Board Of Trustees Of The University Of Illinois | System for controlling the reactivity of boronic acids |
| BRPI0816382A2 (pt) * | 2007-09-06 | 2015-02-24 | Merck Sharp & Dohme | Composto, composição, e, métodos para ativar a guanilato ciclase solúvel e para tratar ou previnir doenças |
| GB0719366D0 (en) | 2007-10-03 | 2007-11-14 | Smithkline Beecham Corp | Compounds |
| JP2011504468A (ja) | 2007-11-13 | 2011-02-10 | プロテズ・ファーマシューティカルズ・インコーポレイテッド | β−ラクタマーゼ阻害剤 |
| US20100120715A1 (en) | 2007-11-13 | 2010-05-13 | Burns Christopher J | Beta-lactamase inhibitors |
| ES2533826T3 (es) | 2008-01-18 | 2015-04-15 | Merck Sharp & Dohme Corp. | Inhibidores de beta-lactamasa |
| US8129398B2 (en) | 2008-03-19 | 2012-03-06 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| EP2285384A4 (en) | 2008-05-12 | 2012-04-25 | Anacor Pharmaceuticals Inc | BORN SMALL MOLECULES |
| CN102098918A (zh) | 2008-05-13 | 2011-06-15 | 帕纳德制药公司 | 用于治疗癌症和神经退行性疾病的生物活性化合物 |
| US20120046242A1 (en) | 2008-12-24 | 2012-02-23 | Massachusetts Institute Of Technology | Molecular activators of the wnt/beta-catenin pathway |
| WO2010097675A1 (en) | 2009-02-27 | 2010-09-02 | Dhanuka Laboratories Ltd. | An improved preparation process for cefpodoxime proxetil |
| EP2406233B1 (en) * | 2009-03-09 | 2013-11-13 | Bristol-Myers Squibb Company | Aza pyridone analogs useful as melanin concentrating hormone receptor-1 antagonists |
| US20100292185A1 (en) | 2009-05-12 | 2010-11-18 | Burns Christopher J | Beta-lactamase inhibitors |
| WO2010144338A1 (en) | 2009-06-08 | 2010-12-16 | Abraxis Bioscience, Llc | Triazine derivatives and their therapeutical applications |
| MX2012001156A (es) | 2009-07-28 | 2012-05-08 | Anacor Pharmaceuticals Inc | Moleculas que contienen boro trisustituidas. |
| EP2539348A4 (en) | 2010-02-26 | 2013-07-24 | Gary Igor Dmitrienko | CEPHALOSPORIN DERIVATIVES AS BETA LACTAMASE HEMMER AND COMPOSITIONS THEREFOR AND METHOD FOR THEIR USE |
| MX2012011298A (es) | 2010-03-31 | 2012-11-06 | Millennium Pharm Inc | Derivados del acido 1-amino-2-ciclopropiletilboronico. |
| US20110288063A1 (en) | 2010-05-19 | 2011-11-24 | Naeja Pharmaceutical Inc. | Novel fused bridged bicyclic heteroaryl substituted 6-alkylidene penems as potent beta-lactamase inhibitors |
| US8822516B2 (en) | 2010-06-10 | 2014-09-02 | Technion Research & Development Foundation Limited | Process for the preparation of iodides |
| RS60310B1 (sr) | 2010-08-10 | 2020-07-31 | Rempex Pharmaceuticals Inc | Ciklični derivati estra boronske kiseline, postupak za pripremu injihove terapeutske upotrebe |
| HRP20160305T1 (hr) | 2010-10-26 | 2016-07-01 | Mars, Incorporated | Borati kao inhibitori arginaze |
| WO2012067664A1 (en) | 2010-11-18 | 2012-05-24 | Glaxo Group Limited | Compounds |
| EP2487159A1 (en) | 2011-02-11 | 2012-08-15 | MSD Oss B.V. | RorgammaT inhibitors |
| EP2508506A1 (en) | 2011-04-08 | 2012-10-10 | LEK Pharmaceuticals d.d. | Preparation of sitagliptin intermediates |
| CN102320960A (zh) | 2011-08-02 | 2012-01-18 | 安徽东健化工科技有限公司 | 一种6-氟水杨酸的制备方法 |
| US9012491B2 (en) | 2011-08-31 | 2015-04-21 | Rempex Pharmaceuticals, Inc. | Heterocyclic boronic acid ester derivatives and therapeutic uses thereof |
| WO2013053372A1 (en) | 2011-10-13 | 2013-04-18 | Therabor Pharmaceuticals | Boronic acid inhibitors of beta-lactamases |
| WO2013056163A1 (en) | 2011-10-14 | 2013-04-18 | The Regents Of The University Of California | Beta-lactamase inhibitors |
| SG11201403254QA (en) | 2011-12-22 | 2014-07-30 | Ares Trading Sa | Alpha-amino boronic acid derivatives, selective immunoproteasome inhibitors |
| EP2802593A1 (en) | 2012-01-09 | 2014-11-19 | The University of Tromsoe | Therapeutic boron-containing compounds |
| EP2615080A1 (en) | 2012-01-12 | 2013-07-17 | LEK Pharmaceuticals d.d. | Preparation of Optically Pure ß-Amino Acid Type Active Pharmaceutical Ingredients and Intermediates thereof |
| EP2814483A2 (en) | 2012-02-15 | 2014-12-24 | Rempex Pharmaceuticals, Inc. | Methods of treating bacterial infections |
| US9156858B2 (en) | 2012-05-23 | 2015-10-13 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| US10561675B2 (en) | 2012-06-06 | 2020-02-18 | Rempex Pharmaceuticals, Inc. | Cyclic boronic acid ester derivatives and therapeutic uses thereof |
| CN105026407B (zh) * | 2012-12-07 | 2017-09-08 | 维纳拓尔斯制药公司 | β‑内酰胺酶抑制剂 |
| KR20150103269A (ko) | 2013-01-04 | 2015-09-09 | 렘펙스 파머수티클스 인코퍼레이티드 | 보론산 유도체 및 그의 치료적 용도 |
| US9101638B2 (en) | 2013-01-04 | 2015-08-11 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| KR20150103270A (ko) | 2013-01-04 | 2015-09-09 | 렘펙스 파머수티클스 인코퍼레이티드 | 보론산 유도체 및 그의 치료적 용도 |
| US9241947B2 (en) | 2013-01-04 | 2016-01-26 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| EP2943204B1 (en) | 2013-01-10 | 2019-03-13 | Venatorx Pharmaceuticals Inc | Beta-lactamase inhibitors |
| WO2014151958A1 (en) | 2013-03-14 | 2014-09-25 | VenatoRx Pharmaceuticals, Inc. | Beta-lactamase inhibitors |
| US9127024B2 (en) | 2013-03-15 | 2015-09-08 | Intrexon Corporation | Boron-containing diacylhydrazines |
| SI3140310T1 (sl) | 2014-05-05 | 2020-01-31 | Rempex Pharmaceuticals, Inc. | Sinteza boronatnih soli in njihova uporaba |
| EP3139930B1 (en) | 2014-05-05 | 2024-08-14 | Melinta Therapeutics, Inc. | Salts and polymorphs of cyclic boronic acid ester derivatives and therapeutic uses thereof |
| WO2015179308A1 (en) | 2014-05-19 | 2015-11-26 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| PT3154989T (pt) | 2014-06-11 | 2021-05-18 | Venatorx Pharmaceuticals Inc | Inibidores de beta-lactamase |
| US9511142B2 (en) | 2014-06-11 | 2016-12-06 | VenatoRx Pharmaceuticals, Inc. | Beta-lactamase inhibitors |
| EA201692301A1 (ru) | 2014-07-01 | 2017-06-30 | Ремпекс Фармасьютикалз, Инк. | Производные бороновой кислоты и их терапевтическое применение |
| WO2016065282A1 (en) | 2014-10-24 | 2016-04-28 | The Regents Of The University Of Michigan | Nasal formulation, nasal kit, and method for enhancing nasal nitric oxide (no) levels |
| WO2016081297A1 (en) | 2014-11-18 | 2016-05-26 | Rempex Pharmaceuticals, Inc. | Cyclic boronic acid ester derivatives and therapeutic uses thereof |
| WO2016116892A1 (en) | 2015-01-24 | 2016-07-28 | Wockhardt Limited | Antibacterial compositions |
| US20180051041A1 (en) | 2015-03-17 | 2018-02-22 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| ES2942329T3 (es) | 2015-04-24 | 2023-05-31 | Melinta Therapeutics Inc | Régimen de dosificación de vaborbactam y meropenem para el tratamiento de infecciones bacterianas en sujetos con función renal reducida |
| WO2017100537A1 (en) | 2015-12-10 | 2017-06-15 | VenatoRx Pharmaceuticals, Inc. | Beta-lactamase inhibitors |
| ES2894251T3 (es) | 2016-06-30 | 2022-02-14 | Qpex Biopharma Inc | Derivados de ácido borónico y usos terapéuticos de los mismos |
| AU2017295866A1 (en) | 2016-07-14 | 2019-01-17 | Achaogen, Inc. | Combination of ceftibuten and clavulanic acid for use in the treatment of bacterial infections |
| CN106397455B (zh) | 2016-08-30 | 2018-08-31 | 山东罗欣药业集团恒欣药业有限公司 | 一种抗感染药物头孢布烯晶体化合物及其组合物 |
| CN106397454B (zh) | 2016-08-30 | 2018-08-24 | 山东罗欣药业集团股份有限公司 | 一种抗感染药物头孢布烯晶型化合物及其组合物 |
| CN114591223B (zh) | 2016-09-16 | 2025-01-24 | 恩塔西斯治疗有限公司 | β-内酰胺酶抑制剂化合物 |
| CN106432271A (zh) | 2016-09-21 | 2017-02-22 | 临沂草之美医药科技有限公司 | 一种治疗外科手术感染的药物头孢布烯晶体化合物 |
| CN106420617A (zh) | 2016-09-21 | 2017-02-22 | 临沂草之美医药科技有限公司 | 一种治疗外科手术感染的药物头孢布烯粉针剂 |
| CN106432272A (zh) | 2016-09-21 | 2017-02-22 | 临沂草之美医药科技有限公司 | 一种制备治疗外科手术感染的药物头孢布烯晶体化合物的方法 |
| CN106397457A (zh) | 2016-09-21 | 2017-02-15 | 临沂草之美医药科技有限公司 | 一种治疗外科手术感染的药物头孢布烯晶体化合物 |
| CN106432270A (zh) | 2016-09-21 | 2017-02-22 | 临沂草之美医药科技有限公司 | 一种制备治疗外科手术感染的药物头孢布烯晶体化合物的方法 |
| CN106420760A (zh) | 2016-09-21 | 2017-02-22 | 临沂草之美医药科技有限公司 | 一种治疗外科手术感染的药物头孢布烯组合物 |
| US10085999B1 (en) | 2017-05-10 | 2018-10-02 | Arixa Pharmaceuticals, Inc. | Beta-lactamase inhibitors and uses thereof |
| MX2020003495A (es) | 2017-10-11 | 2020-09-18 | Qpex Biopharma Inc | Derivados de acido boronico y sintesis de los mismos. |
| WO2019093450A1 (ja) | 2017-11-10 | 2019-05-16 | 塩野義製薬株式会社 | ジアザビシクロオクタン誘導体 |
| US12016868B2 (en) | 2018-04-20 | 2024-06-25 | Qpex Biopharma, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| CN109293678A (zh) | 2018-11-20 | 2019-02-01 | 湖北凌晟药业有限公司 | 一种头孢布烯的制备方法 |
| CN113382713A (zh) | 2018-11-29 | 2021-09-10 | 维纳拓尔斯制药公司 | 包含β-内酰胺酶抑制剂的组合式组合物及其用途 |
| PL3986419T3 (pl) | 2019-06-19 | 2025-09-08 | Qpex Biopharma, Inc. | Pochodne kwasu boronowego i ich zastosowania terapeutyczne |
| MX2022002537A (es) | 2019-08-29 | 2022-03-22 | Arixa Pharmaceuticals Inc | Combinaciones administradas via oral de antibioticos beta-lactama y derivados de avibactam para tratar infecciones bacterianas. |
| WO2021188700A1 (en) | 2020-03-18 | 2021-09-23 | Qpex Biopharma, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| BR112022022367A2 (pt) | 2020-05-05 | 2023-01-10 | Qpex Biopharma Inc | Derivados e síntese de ácido borônico, formas polimórficas e usos terapêuticos dos mesmos |
| EP4319760A4 (en) | 2021-04-05 | 2025-01-08 | Qpex Biopharma, Inc. | CEFTIBUTENE DOSAGE REGIMEN |
| EP4362950A4 (en) | 2021-07-01 | 2025-08-13 | Qpex Biopharma Inc | CRYSTALLINE FORMS OF CEFTIBUTEN |
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