KR20150103269A - 보론산 유도체 및 그의 치료적 용도 - Google Patents
보론산 유도체 및 그의 치료적 용도 Download PDFInfo
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- KR20150103269A KR20150103269A KR1020157021053A KR20157021053A KR20150103269A KR 20150103269 A KR20150103269 A KR 20150103269A KR 1020157021053 A KR1020157021053 A KR 1020157021053A KR 20157021053 A KR20157021053 A KR 20157021053A KR 20150103269 A KR20150103269 A KR 20150103269A
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- 150000001642 boronic acid derivatives Chemical class 0.000 title abstract description 13
- 230000001225 therapeutic effect Effects 0.000 title description 5
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- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims abstract description 12
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- 125000000217 alkyl group Chemical group 0.000 claims description 208
- 125000003118 aryl group Chemical group 0.000 claims description 84
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 71
- 229910052736 halogen Inorganic materials 0.000 claims description 59
- 150000002367 halogens Chemical class 0.000 claims description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims description 57
- 229930186147 Cephalosporin Natural products 0.000 claims description 56
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- 150000003839 salts Chemical class 0.000 claims description 54
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- WZPBZJONDBGPKJ-VEHQQRBSSA-N aztreonam Chemical group 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 claims description 46
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 42
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 31
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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 claims description 22
- 125000000304 alkynyl group Chemical group 0.000 claims description 22
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 18
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- ZSKVGTPCRGIANV-ZXFLCMHBSA-N imipenem Chemical compound C1C(SCC\N=C\N)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 ZSKVGTPCRGIANV-ZXFLCMHBSA-N 0.000 claims description 15
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- 229910052796 boron Inorganic materials 0.000 claims description 13
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- VAAUVRVFOQPIGI-SPQHTLEESA-N ceftriaxone Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=NC(=O)C(=O)NN1C VAAUVRVFOQPIGI-SPQHTLEESA-N 0.000 claims description 13
- 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 claims description 13
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- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims description 12
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 241000124008 Mammalia Species 0.000 claims description 12
- TYMABNNERDVXID-DLYFRVTGSA-N Panipenem Chemical compound C([C@@H]1[C@H](C(N1C=1C(O)=O)=O)[C@H](O)C)C=1S[C@H]1CCN(C(C)=N)C1 TYMABNNERDVXID-DLYFRVTGSA-N 0.000 claims description 12
- 241000589516 Pseudomonas Species 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 239000003242 anti bacterial agent Substances 0.000 claims description 12
- AVAACINZEOAHHE-VFZPANTDSA-N doripenem 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](CNS(N)(=O)=O)C1 AVAACINZEOAHHE-VFZPANTDSA-N 0.000 claims description 12
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- 239000003937 drug carrier Substances 0.000 claims description 12
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- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 claims description 11
- 229960000484 ceftazidime Drugs 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- JETQIUPBHQNHNZ-NJBDSQKTSA-N (2s,5r,6r)-3,3-dimethyl-7-oxo-6-[[(2r)-2-phenyl-2-sulfoacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound C1([C@H](C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)S(O)(=O)=O)=CC=CC=C1 JETQIUPBHQNHNZ-NJBDSQKTSA-N 0.000 claims description 10
- LZKPUSJSJVEXAW-WDXSGGTDSA-N (4s,5r,6s)-3-[7-[1-(2-amino-2-oxoethyl)pyridin-1-ium-3-carbonyl]imidazo[5,1-b][1,3]thiazol-2-yl]-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C([O-])=O)=O)[C@H](O)C)C(SC1=2)=CN1C=NC=2C(=O)C1=CC=C[N+](CC(N)=O)=C1 LZKPUSJSJVEXAW-WDXSGGTDSA-N 0.000 claims description 10
- 241000606125 Bacteroides Species 0.000 claims description 10
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 10
- 241000191940 Staphylococcus Species 0.000 claims description 10
- KLFSEZJCLYBFKQ-WXYNYTDUSA-N [(3s)-3-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1,5-dihydroxy-4-oxopyridin-2-yl)methoxyimino]acetyl]amino]-2,2-dimethyl-4-oxoazetidin-1-yl] hydrogen sulfate Chemical compound O=C1N(OS(O)(=O)=O)C(C)(C)[C@@H]1NC(=O)C(\C=1N=C(N)SC=1)=N/OCC1=CC(=O)C(O)=CN1O KLFSEZJCLYBFKQ-WXYNYTDUSA-N 0.000 claims description 10
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- PFOLLRNADZZWEX-FFGRCDKISA-N bacampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)[C@H](C(S3)(C)C)C(=O)OC(C)OC(=O)OCC)=CC=CC=C1 PFOLLRNADZZWEX-FFGRCDKISA-N 0.000 claims description 10
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
- MZAGXDHQGXUDDX-JSRXJHBZSA-N (e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/C(N)=O MZAGXDHQGXUDDX-JSRXJHBZSA-N 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
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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 claims description 9
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 claims description 7
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- CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical compound O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 claims description 7
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- ZBHXIWJRIFEVQY-IHMPYVIRSA-N ceftiofur Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC(=O)C1=CC=CO1 ZBHXIWJRIFEVQY-IHMPYVIRSA-N 0.000 claims description 7
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- ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 claims description 7
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
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- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 6
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
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- 125000004104 aryloxy group Chemical group 0.000 claims description 6
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Classifications
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—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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- A61K31/395—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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- 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
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
- A61K31/546—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine containing further heterocyclic rings, e.g. cephalothin
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- A—HUMAN NECESSITIES
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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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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- 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
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- Medicinal Preparation (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
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| WO2013033461A1 (en) | 2011-08-31 | 2013-03-07 | Rempex Pharmaceuticals, Inc. | Heterocyclic boronic acid ester derivatives and therapeutic uses thereof |
| US9642896B1 (en) | 2011-11-14 | 2017-05-09 | Yale University | Compositions and methods for modulating coagulation |
| US10561675B2 (en) | 2012-06-06 | 2020-02-18 | Rempex Pharmaceuticals, Inc. | Cyclic boronic acid ester derivatives and therapeutic uses thereof |
| KR102147420B1 (ko) | 2012-12-07 | 2020-08-25 | 베나토알엑스 파마슈티컬스, 인크. | 베타-락타마제 억제제 |
| BR112015016002A2 (pt) | 2013-01-04 | 2017-07-11 | Rempex Pharmaceuticals Inc | compostos, composições farmacêuticas, complexos químicos e respectivos usos e método para tratar ou prevenir infecção bacteriana |
| CA2894891A1 (en) | 2013-01-04 | 2014-07-10 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| US9241947B2 (en) | 2013-01-04 | 2016-01-26 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| US9403850B2 (en) | 2013-01-10 | 2016-08-02 | VenatoRx Pharmaceuticals, Inc. | Beta-lactamase inhibitors |
| WO2014151958A1 (en) | 2013-03-14 | 2014-09-25 | VenatoRx Pharmaceuticals, Inc. | Beta-lactamase inhibitors |
| ES2750805T3 (es) | 2014-05-05 | 2020-03-27 | Rempex Pharmaceuticals Inc | Síntesis de sales de boronato y usos de las mismas |
| WO2015171398A1 (en) | 2014-05-05 | 2015-11-12 | Rempex Pharmaceuticals, Inc. | Salts and polymorphs of cyclic boronic acid ester derivatives and therapeutic uses thereof |
| EA201691988A1 (ru) * | 2014-05-19 | 2017-06-30 | Ремпекс Фармасьютикалз, Инк. | Производные бороновой кислоты и их терапевтическое применение |
| PL3154989T3 (pl) * | 2014-06-11 | 2021-10-18 | VenatoRx Pharmaceuticals, Inc. | Inhibitory beta-laktamaz |
| US9511142B2 (en) | 2014-06-11 | 2016-12-06 | VenatoRx Pharmaceuticals, Inc. | Beta-lactamase inhibitors |
| US10206937B2 (en) | 2014-07-01 | 2019-02-19 | Qpex Biopharma, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| WO2016081297A1 (en) | 2014-11-18 | 2016-05-26 | Rempex Pharmaceuticals, Inc. | Cyclic boronic acid ester derivatives and therapeutic uses thereof |
| WO2016149393A1 (en) | 2015-03-17 | 2016-09-22 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| WO2016165019A1 (en) * | 2015-04-14 | 2016-10-20 | B-Organic Films Corp. | Antiviral and antibacteria agents based on quaternary ammonium compound complexed with boric acid and its derivatives |
| EP3347008B1 (en) * | 2015-09-11 | 2022-03-09 | Venatorx Pharmaceuticals, Inc. | Beta-lactamase inhibitors |
| WO2017100537A1 (en) | 2015-12-10 | 2017-06-15 | VenatoRx Pharmaceuticals, Inc. | Beta-lactamase inhibitors |
| CN105801610B (zh) * | 2016-04-19 | 2018-05-18 | 武汉维舜医药科技有限公司 | 新型广谱β-内酰胺酶抑制剂 |
| WO2017190043A1 (en) * | 2016-04-29 | 2017-11-02 | University Of Kansas | Cephalosporin-type compounds |
| AU2017290060B2 (en) | 2016-06-30 | 2021-07-22 | Qpex Biopharma, Inc | Boronic acid derivatives and therapeutic uses thereof |
| US10889600B2 (en) | 2016-08-04 | 2021-01-12 | VenatoRx Pharmaceuticals, Inc. | Boron-containing compounds |
| JOP20190188A1 (ar) * | 2017-02-01 | 2019-08-01 | Rempex Pharmaceuticals Inc | جهاز وعملية تدفق مستمرة لإنتاج مشتق حمض بورونيك |
| PL3592362T3 (pl) | 2017-03-06 | 2025-06-23 | VenatoRx Pharmaceuticals, Inc. | Postacie stałe i kompozycje skojarzone zawierające inhibitor beta-laktamaz i ich zastosowania |
| WO2018218154A1 (en) | 2017-05-26 | 2018-11-29 | VenatoRx Pharmaceuticals, Inc. | Penicillin-binding protein inhibitors |
| CN110959008A (zh) * | 2017-05-26 | 2020-04-03 | 维纳拓尔斯制药公司 | 青霉素结合蛋白抑制剂 |
| EP3687565A1 (en) | 2017-09-27 | 2020-08-05 | Alexion Pharmaceuticals, Inc. | Methods of improving cardiovascular function and treating cardiovascular disease using a recombinant ectonucleotide pyrophosphatase phosphodiesterase (npp1) |
| BR112020007138B1 (pt) | 2017-10-11 | 2023-03-21 | Qpex Biopharma, Inc | Derivados de ácido borônico, métodos de síntese, composição farmacêutica e uso dos mesmos |
| EP3781576B1 (en) | 2018-04-20 | 2024-06-12 | Qpex Biopharma, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| EP3786168A4 (en) | 2018-04-27 | 2022-03-23 | Sumitomo Dainippon Pharma Co., Ltd. | OXO-SUBSTITUTED COMPOUND |
| CN112469725A (zh) | 2018-05-25 | 2021-03-09 | 维纳拓尔斯制药公司 | 青霉素结合蛋白抑制剂 |
| KR20210097758A (ko) * | 2018-11-29 | 2021-08-09 | 베나토알엑스 파마슈티컬스, 인크. | 베타-락타마제 억제제를 포함하는 조합 조성물 및 이의 용도 |
| CA3135614A1 (en) * | 2019-04-02 | 2020-10-08 | VenatoRx Pharmaceuticals, Inc. | Solid forms of an orally-delivered beta-lactamase inhibitor and uses thereof |
| PH12022550983A1 (en) | 2019-10-25 | 2023-10-09 | Sumitomo Pharma Co Ltd | Novel substituted condensed ring compound |
| EP4301466A4 (en) * | 2021-03-02 | 2025-08-20 | Univ Case Western Reserve | BETA-LACTAMASE INHIBITORS AND THEIR USES |
| 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 |
| 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 |
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2014
- 2014-01-02 CA CA2894891A patent/CA2894891A1/en not_active Abandoned
- 2014-01-02 CN CN201480003981.3A patent/CN104994844A/zh active Pending
- 2014-01-02 BR BR112015016001A patent/BR112015016001A2/pt not_active IP Right Cessation
- 2014-01-02 WO PCT/US2014/010106 patent/WO2014107535A1/en not_active Ceased
- 2014-01-02 JP JP2015551761A patent/JP2016509594A/ja active Pending
- 2014-01-02 EA EA201591003A patent/EA201591003A1/ru unknown
- 2014-01-02 US US14/146,671 patent/US9642869B2/en not_active Expired - Fee Related
- 2014-01-02 AU AU2014204045A patent/AU2014204045B2/en not_active Expired - Fee Related
- 2014-01-02 EP EP14735173.8A patent/EP2941246A4/en not_active Withdrawn
- 2014-01-02 MX MX2015008628A patent/MX2015008628A/es unknown
- 2014-01-02 KR KR1020157021053A patent/KR20150103269A/ko not_active Withdrawn
- 2014-01-03 TW TW103100234A patent/TW201431866A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2014204045B2 (en) | 2018-10-18 |
| CA2894891A1 (en) | 2014-07-10 |
| TW201431866A (zh) | 2014-08-16 |
| AU2014204045A1 (en) | 2015-07-16 |
| WO2014107535A1 (en) | 2014-07-10 |
| EP2941246A1 (en) | 2015-11-11 |
| US20140194385A1 (en) | 2014-07-10 |
| BR112015016001A2 (pt) | 2017-07-11 |
| US9642869B2 (en) | 2017-05-09 |
| EA201591003A1 (ru) | 2015-12-30 |
| EP2941246A4 (en) | 2016-12-21 |
| MX2015008628A (es) | 2015-09-23 |
| CN104994844A (zh) | 2015-10-21 |
| JP2016509594A (ja) | 2016-03-31 |
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