KR20170024087A - 보론산 유도체 및 그의 치료적 용도 - Google Patents

보론산 유도체 및 그의 치료적 용도 Download PDF

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Publication number: KR20170024087A
Authority: KR; South Korea
Prior art keywords: alkyl; optionally substituted; compound; group; halogen
Prior art date: 2014-07-01
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

KR1020177002769A

Other languages

English (en)

Korean (ko)

Inventor

라자 케이. 레디

토마스 글린카

맥심 토트로브

스콧 헤커

올가 로드니

Original Assignee

렘펙스 파머수티클스 인코퍼레이티드

Priority date (The priority date 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 date listed.)

2014-07-01

Filing date

2015-06-29

Publication date

2017-03-06

2015-06-29 Application filed by 렘펙스 파머수티클스 인코퍼레이티드 filed Critical 렘펙스 파머수티클스 인코퍼레이티드

2017-03-06 Publication of KR20170024087A publication Critical patent/KR20170024087A/ko

Status Withdrawn legal-status Critical Current

Links

150000001642 boronic acid derivatives Chemical class 0.000 title abstract description 9
230000001225 therapeutic effect Effects 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 588
238000000034 method Methods 0.000 claims abstract description 200
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 33
239000003814 drug Substances 0.000 claims abstract description 28
125000000217 alkyl group Chemical group 0.000 claims description 228
-1 substituted Chemical class 0.000 claims description 208
206010057190 Respiratory tract infections Diseases 0.000 claims description 130
125000000623 heterocyclic group Chemical group 0.000 claims description 110
125000003118 aryl group Chemical group 0.000 claims description 107
229910052736 halogen Inorganic materials 0.000 claims description 101
150000002367 halogens Chemical class 0.000 claims description 100
125000001424 substituent group Chemical group 0.000 claims description 78
125000004093 cyano group Chemical group *C#N 0.000 claims description 65
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 64
125000004452 carbocyclyl group Chemical group 0.000 claims description 57
125000003396 thiol group Chemical group [H]S* 0.000 claims description 56
125000005843 halogen group Chemical group 0.000 claims description 55
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 53
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 50
150000001412 amines Chemical group 0.000 claims description 47
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 45
125000002947 alkylene group Chemical group 0.000 claims description 43
150000003839 salts Chemical class 0.000 claims description 42
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 41
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 35
239000003795 chemical substances by application Substances 0.000 claims description 35
125000000304 alkynyl group Chemical group 0.000 claims description 31
229910052739 hydrogen Inorganic materials 0.000 claims description 29
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 29
229910052757 nitrogen Inorganic materials 0.000 claims description 25
239000001257 hydrogen Substances 0.000 claims description 23
229940079593 drug Drugs 0.000 claims description 21
125000001072 heteroaryl group Chemical group 0.000 claims description 20
239000000546 pharmaceutical excipient Substances 0.000 claims description 19
238000011282 treatment Methods 0.000 claims description 19
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 18
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125000004429 atom Chemical group 0.000 claims description 18
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 16
229910052799 carbon Inorganic materials 0.000 claims description 16
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 15
239000000460 chlorine Substances 0.000 claims description 15
150000002771 monosaccharide derivatives Chemical class 0.000 claims description 15
125000006545 (C1-C9) alkyl group Chemical group 0.000 claims description 14
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125000005842 heteroatom Chemical group 0.000 claims description 14
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208000022362 bacterial infectious disease Diseases 0.000 claims description 13
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 13
150000003852 triazoles Chemical class 0.000 claims description 13
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 12
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 12
150000002772 monosaccharides Chemical class 0.000 claims description 12
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 11
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 11
125000004104 aryloxy group Chemical group 0.000 claims description 11
239000003782 beta lactam antibiotic agent Substances 0.000 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
239000000126 substance Substances 0.000 claims description 11
125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims description 10
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 10
241000124008 Mammalia Species 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
241000606125 Bacteroides Species 0.000 claims description 9
229930186147 Cephalosporin Natural products 0.000 claims description 9
241000589516 Pseudomonas Species 0.000 claims description 9
229910052796 boron Inorganic materials 0.000 claims description 9
150000001735 carboxylic acids Chemical class 0.000 claims description 9
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150000001780 cephalosporins Chemical class 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 9
125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 8
125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 claims description 8
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 8
239000003242 anti bacterial agent Substances 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical group CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 7
WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 claims description 7
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 7
229960003644 aztreonam Drugs 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
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 7
229960002182 imipenem Drugs 0.000 claims description 7
208000015181 infectious disease Diseases 0.000 claims description 7
229960003194 meglumine Drugs 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
150000003536 tetrazoles Chemical class 0.000 claims description 7
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 7
241000894006 Bacteria Species 0.000 claims description 6
241000606790 Haemophilus Species 0.000 claims description 6
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 6
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 6
241000191940 Staphylococcus Species 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
229960000484 ceftazidime Drugs 0.000 claims description 6
ORFOPKXBNMVMKC-DWVKKRMSSA-N ceftazidime Chemical compound S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC(C)(C)C(O)=O)C=2N=C(N)SC=2)CC=1C[N+]1=CC=CC=C1 ORFOPKXBNMVMKC-DWVKKRMSSA-N 0.000 claims description 6
235000019371 penicillin G benzathine Nutrition 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 6
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 5
241000589876 Campylobacter Species 0.000 claims description 5
241000606768 Haemophilus influenzae Species 0.000 claims description 5
241000606860 Pasteurella Species 0.000 claims description 5
229940121375 antifungal agent Drugs 0.000 claims description 5
239000003429 antifungal agent Substances 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
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 5
229960000895 doripenem Drugs 0.000 claims description 5
229940047650 haemophilus influenzae Drugs 0.000 claims description 5
125000002883 imidazolyl group Chemical group 0.000 claims description 5
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 5
229960002260 meropenem Drugs 0.000 claims description 5
229940056360 penicillin g Drugs 0.000 claims description 5
YWKJNRNSJKEFMK-PQFQYKRASA-N (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-(5,6,7,8-tetrahydroquinolin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound N([C@@H]1C(N2C(=C(C[N+]=3C=4CCCCC=4C=CC=3)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 YWKJNRNSJKEFMK-PQFQYKRASA-N 0.000 claims description 4
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
241000589291 Acinetobacter Species 0.000 claims description 4
241000607528 Aeromonas hydrophila Species 0.000 claims description 4
241000606219 Bacteroides uniformis Species 0.000 claims description 4
241000588914 Enterobacter Species 0.000 claims description 4
241000194032 Enterococcus faecalis Species 0.000 claims description 4
241000590002 Helicobacter pylori Species 0.000 claims description 4
241000588748 Klebsiella Species 0.000 claims description 4
241000589242 Legionella pneumophila Species 0.000 claims description 4
229930195708 Penicillin V Natural products 0.000 claims description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
241000589517 Pseudomonas aeruginosa Species 0.000 claims description 4
241000607142 Salmonella Species 0.000 claims description 4
241000607720 Serratia Species 0.000 claims description 4
241000607768 Shigella Species 0.000 claims description 4
241000191967 Staphylococcus aureus Species 0.000 claims description 4
241000191963 Staphylococcus epidermidis Species 0.000 claims description 4
241000193998 Streptococcus pneumoniae Species 0.000 claims description 4
241000607734 Yersinia <bacteria> Species 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 4
AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin 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=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims description 4
229950009592 cefquinome Drugs 0.000 claims description 4
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 4
229960005229 ceftiofur Drugs 0.000 claims description 4
229940032049 enterococcus faecalis Drugs 0.000 claims description 4
229940037467 helicobacter pylori Drugs 0.000 claims description 4
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125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
229940056367 penicillin v Drugs 0.000 claims description 4
BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 claims description 4
229940031000 streptococcus pneumoniae Drugs 0.000 claims description 4
125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
125000000858 thiocyanato group Chemical group *SC#N 0.000 claims description 4
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 4
229950010206 tigemonam Drugs 0.000 claims description 4
229940124586 β-lactam antibiotics Drugs 0.000 claims description 4
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 3
FMZXNVLFJHCSAF-DNVCBOLYSA-N (6R,7R)-3-[(4-carbamoyl-1-pyridin-1-iumyl)methyl]-8-oxo-7-[(1-oxo-2-thiophen-2-ylethyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1=CC(C(=O)N)=CC=[N+]1CC1=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CC=3SC=CC=3)[C@H]2SC1 FMZXNVLFJHCSAF-DNVCBOLYSA-N 0.000 claims description 3
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241000588807 Bordetella Species 0.000 claims description 3
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UQLLWWBDSUHNEB-CZUORRHYSA-N Cefaprin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CSC1=CC=NC=C1 UQLLWWBDSUHNEB-CZUORRHYSA-N 0.000 claims description 3
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241000193403 Clostridium Species 0.000 claims description 3
241000588724 Escherichia coli Species 0.000 claims description 3
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241000606822 Haemophilus parahaemolyticus Species 0.000 claims description 3
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241000588747 Klebsiella pneumoniae Species 0.000 claims description 3
241000186364 Mycobacterium intracellulare Species 0.000 claims description 3
241000187479 Mycobacterium tuberculosis Species 0.000 claims description 3
241001135232 Odoribacter splanchnicus Species 0.000 claims description 3
201000005702 Pertussis Diseases 0.000 claims description 3
241000588770 Proteus mirabilis Species 0.000 claims description 3
241000588767 Proteus vulgaris Species 0.000 claims description 3
241000168225 Pseudomonas alcaligenes Species 0.000 claims description 3
241000589776 Pseudomonas putida Species 0.000 claims description 3
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
125000005631 S-sulfonamido group Chemical group 0.000 claims description 3
241000191984 Staphylococcus haemolyticus Species 0.000 claims description 3
241000191980 Staphylococcus intermedius Species 0.000 claims description 3
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150000001408 amides Chemical group 0.000 claims description 3
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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 3
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239000002260 anti-inflammatory agent Substances 0.000 claims description 3
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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 3
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FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 claims description 3
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JIRBAUWICKGBFE-MNRDOXJOSA-N carindacillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(=O)OC=1C=C2CCCC2=CC=1)C1=CC=CC=C1 JIRBAUWICKGBFE-MNRDOXJOSA-N 0.000 claims description 3
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QYIYFLOTGYLRGG-GPCCPHFNSA-N cefaclor Chemical compound C1([C@H](C(=O)N[C@@H]2C(N3C(=C(Cl)CS[C@@H]32)C(O)=O)=O)N)=CC=CC=C1 QYIYFLOTGYLRGG-GPCCPHFNSA-N 0.000 claims description 3
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DZMVCVMFETWNIU-LDYMZIIASA-N ceftezole Chemical compound O=C([C@@H](NC(=O)CN1N=NN=C1)[C@H]1SC2)N1C(C(=O)O)=C2CSC1=NN=CS1 DZMVCVMFETWNIU-LDYMZIIASA-N 0.000 claims description 3
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JFPVXVDWJQMJEE-IZRZKJBUSA-N cefuroxime Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 JFPVXVDWJQMJEE-IZRZKJBUSA-N 0.000 claims description 3
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 3
125000001810 isothiocyanato group Chemical group *N=C=S 0.000 claims description 3
125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 3
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 3
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Classifications

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- A61K31/69—Boron compounds
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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
- A—HUMAN NECESSITIES
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- 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
- A61K31/41—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
- 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
- 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
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
- 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

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CA (1)	CA2952968A1 (2)
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Families Citing this family (39)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RS60310B1 (sr)	2010-08-10	2020-07-31	Rempex Pharmaceuticals Inc	Ciklični derivati estra boronske kiseline, postupak za pripremu injihove terapeutske upotrebe
KR20150103269A (ko)	2013-01-04	2015-09-09	렘펙스 파머수티클스 인코퍼레이티드	보론산 유도체 및 그의 치료적 용도
EP2943204B1 (en) *	2013-01-10	2019-03-13	Venatorx Pharmaceuticals Inc	Beta-lactamase inhibitors
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
US9511142B2 (en)	2014-06-11	2016-12-06	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
WO2017100537A1 (en)	2015-12-10	2017-06-15	VenatoRx Pharmaceuticals, Inc.	Beta-lactamase inhibitors
CN106008446A (zh) *	2016-04-29	2016-10-12	广州药本君安医药科技股份有限公司	呫吨酮衍生物及呫吨酮和其衍生物的制备方法与用途
ES2894251T3 (es) *	2016-06-30	2022-02-14	Qpex Biopharma Inc	Derivados de ácido borónico y usos terapéuticos de los mismos
FR3053968A1 (fr) *	2016-07-13	2018-01-19	Biomerieux	Reactifs pour la protection reversible de molecules biologiques
EP3494121B1 (en)	2016-08-04	2021-10-06	Venatorx Pharmaceuticals, Inc.	Boron-containing compounds
GB201613946D0 (en)	2016-08-15	2016-09-28	Univ Oslo	Compounds
JOP20190188A1 (ar)	2017-02-01	2019-08-01	Rempex Pharmaceuticals Inc	جهاز وعملية تدفق مستمرة لإنتاج مشتق حمض بورونيك
TW201841642A (zh) *	2017-04-28	2018-12-01	日商大日本住友製藥股份有限公司	雜環衍生物
US11332485B2 (en)	2017-05-26	2022-05-17	VenatoRx Pharmaceuticals, Inc.	Penicillin-binding protein inhibitors
EP3630783A4 (en)	2017-05-26	2021-03-03	Venatorx Pharmaceuticals, Inc.	PENICILLIN-BINDING PROTEIN INHIBITORS
WO2019009369A1 (ja) *	2017-07-06	2019-01-10	大日本住友製薬株式会社	イミン誘導体
WO2019009370A1 (ja) *	2017-07-06	2019-01-10	大日本住友製薬株式会社	アミド誘導体
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
CA3098433A1 (en) *	2018-04-27	2019-10-31	Sumitomo Dainippon Pharma Co., Ltd.	Oxo-substituted compound
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
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
JP7550421B2 (ja) *	2019-10-25	2024-09-13	住友ファーマ株式会社	オキソ置換化合物からなる医薬
BR112022010924A2 (pt)	2019-12-06	2022-09-06	Vertex Pharma	Tetra-hidrofuranos substituídos como moduladores de canais de sódio
CN110938015B (zh) *	2019-12-06	2022-10-25	重庆工商大学	一种叠氮基取代的水杨酸衍生物的制备方法
BR112022022367A2 (pt)	2020-05-05	2023-01-10	Qpex Biopharma Inc	Derivados e síntese de ácido borônico, formas polimórficas e usos terapêuticos dos mesmos
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
SMT202500481T1 (it)	2021-06-04	2026-01-12	Vertex Pharma	N-(idrossialchil(etero)aril)tetraidrofuran carbossammidi come modulatori di canali del sodio
CN117343088A (zh) *	2022-07-05	2024-01-05	福安药业集团重庆三禾兴医药科技有限公司	一类7-((五元杂环)甲基)-8-羧酸-苯并环硼酸酯类衍生物及其用途
US20250099495A1 (en) *	2023-09-22	2025-03-27	City University Of Hong Kong	Methods of inhibiting klebsiella pneumoniae carbapenemase-2
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

Family Cites Families (110)

* Cited by examiner, † Cited by third party
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
US4758557A (en)	1985-06-26	1988-07-19	Meiji Seika Kaisha, Ltd.	Cephalosporin derivatives and bactericides containing the same
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
US5028601A (en)	1987-04-30	1991-07-02	Meiji Saika Kaisha, Ltd.	Cephalosporin compounds and antibacterial agents
EP0333082A3 (en)	1988-03-15	1991-05-02	Takeda Chemical Industries, Ltd.	Cephem compounds, their production and use
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
GB9601680D0 (en)	1996-01-27	1996-03-27	Pfizer Ltd	Therapeutic agents
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
TR200101903T2 (tr)	1999-01-02	2001-11-21	Aventis Pharma Deutschland Gmbh	Yeni malonik asit türevleri, bunların preparasyon işlemleri.
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
AU2004224807A1 (en)	2003-03-24	2004-10-07	Axikin Pharmaceuticals, Inc.	2-phenoxy- and 2-phenylsulfomamide derivatives with CCR3 antagonistic activity for the treatment of asthma and other inflammatory or immunological disorders
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
CA2530014A1 (en)	2003-08-27	2005-03-10	Eli Lilly And Company	Treatment of learning disabilities and motor skills disorder with norepinephrine reuptake inhibitors
JP2005089383A (ja)	2003-09-18	2005-04-07	Bayer Cropscience Ag	新規チアジアゾール含有ジフルオロアルケン類及び有害生物防除剤としての利用
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
KR100648133B1 (ko)	2005-04-25	2006-11-23	일동제약주식회사	펩티드 데포르밀라제 저해제로서 신규의 히드록사믹 산유도체 및 그 제조방법
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
GB0719366D0 (en)	2007-10-03	2007-11-14	Smithkline Beecham Corp	Compounds
US20100120715A1 (en) *	2007-11-13	2010-05-13	Burns Christopher J	Beta-lactamase inhibitors
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
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
US20110039895A1 (en)	2008-04-30	2011-02-17	Glaxo Smith Kline LLC., a corporation	Prolyl hydroxylase 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
WO2010030811A2 (en)	2008-09-10	2010-03-18	Achaogen, Inc.	CARBACEPHEM β-LACTAM ANTIBIOTICS
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
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.
CN102153553A (zh)	2010-02-11	2011-08-17	山东轩竹医药科技有限公司	含有氨基磺酰胺基氮杂环丁烷的口服碳青霉烯化合物
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.
FR2959061B1 (fr)	2010-04-20	2012-05-11	Commissariat Energie Atomique	Substrat fonctionnalise et ses applications
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
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
ITTO20111013A1 (it)	2011-11-03	2013-05-04	Dac Srl	Composti farmaceutici
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
WO2013160810A2 (en)	2012-04-24	2013-10-31	Hetero Research Foundation	Novel betulinic acid derivatives as hiv inhibitors
EP2844249A4 (en)	2012-05-02	2016-03-09	Univ Kansas State	MACROCYCLIC AND PEPTIDOMIMETIC COMPOUNDS AS VIRUZIDES AGAINST 3C OR 3C LIKE PROTEASES OF PICORNIVERS, CALICIVIRES AND CORONA VIRUSES
MX2014014109A (es)	2012-05-23	2016-03-31	Savira Pharmaceuticals Gmbh	Derivados de 7-oxo-4,7-dihidro-pirazolo[1,5-a]pirimidina que son utiles en el tratamiento, mejora o prevencion de una enfermedad viral.
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
US9101638B2 (en)	2013-01-04	2015-08-11	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
KR20150103269A (ko)	2013-01-04	2015-09-09	렘펙스 파머수티클스 인코퍼레이티드	보론산 유도체 및 그의 치료적 용도
KR20150103270A (ko)	2013-01-04	2015-09-09	렘펙스 파머수티클스 인코퍼레이티드	보론산 유도체 및 그의 치료적 용도
US8999885B2 (en)	2013-01-09	2015-04-07	General Electric Company	Methods of activating charcoal resulting from biomass gasification
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
US20160039879A1 (en)	2013-03-15	2016-02-11	S&T Global Inc.	Novel cyclosporin derivatives and uses thereof
EP3139930B1 (en)	2014-05-05	2024-08-14	Melinta Therapeutics, Inc.	Salts and polymorphs of cyclic boronic acid ester derivatives and therapeutic uses thereof
SI3140310T1 (sl)	2014-05-05	2020-01-31	Rempex Pharmaceuticals, Inc.	Sinteza boronatnih soli in njihova uporaba
WO2015179308A1 (en)	2014-05-19	2015-11-26	Rempex Pharmaceuticals, Inc.	Boronic acid derivatives and therapeutic uses thereof
US9511142B2 (en)	2014-06-11	2016-12-06	VenatoRx Pharmaceuticals, Inc.	Beta-lactamase inhibitors
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
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

2015
- 2015-06-29 EA EA201692301A patent/EA201692301A1/ru unknown
- 2015-06-29 CN CN201580039809.8A patent/CN106536529B/zh active Active
- 2015-06-29 AU AU2015284307A patent/AU2015284307A1/en not_active Abandoned
- 2015-06-29 KR KR1020177002769A patent/KR20170024087A/ko not_active Withdrawn
- 2015-06-29 US US15/323,081 patent/US10206937B2/en active Active
- 2015-06-29 WO PCT/US2015/038364 patent/WO2016003929A1/en not_active Ceased
- 2015-06-29 JP JP2016575893A patent/JP6700203B2/ja active Active
- 2015-06-29 CA CA2952968A patent/CA2952968A1/en not_active Abandoned
- 2015-06-29 EP EP15815718.0A patent/EP3164406B1/en active Active
- 2015-06-29 MX MX2016016666A patent/MX2016016666A/es unknown
2016
- 2016-12-15 ZA ZA2016/08682A patent/ZA201608682B/en unknown

Also Published As

Publication number	Publication date
JP6700203B2 (ja)	2020-05-27
JP2017526636A (ja)	2017-09-14
MX2016016666A (es)	2017-08-08
EP3164406C0 (en)	2024-12-25
CA2952968A1 (en)	2016-01-07
EA201692301A1 (ru)	2017-06-30
WO2016003929A1 (en)	2016-01-07
EP3164406A4 (en)	2018-04-04
CN106536529B (zh)	2019-09-27
CN106536529A (zh)	2017-03-22
EP3164406B1 (en)	2024-12-25
EP3164406A1 (en)	2017-05-10
AU2015284307A1 (en)	2017-02-02
US10206937B2 (en)	2019-02-19
US20170136047A1 (en)	2017-05-18
ZA201608682B (en)	2019-06-26

Legal Events

Date

Code

Title

Description

2017-01-31

PA0105

International application

Patent event date: 20170131

Patent event code: PA01051R01D

Comment text: International Patent Application