SK2462003A3 - 3-(Heteroaryl acetamido)-2-oxo-azetidine-1-sulfonic acids derivatives as antibacterial agents - Google Patents

3-(Heteroaryl acetamido)-2-oxo-azetidine-1-sulfonic acids derivatives as antibacterial agents Download PDF

Info

Publication number: SK2462003A3
Authority: SK; Slovakia
Prior art keywords: compound; formula; hydrogen; acetamido; pharmaceutically acceptable
Prior art date: 2000-09-14

Application number

SK246-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Ronald George Micetich

Samarendra Nath Maiti

Charles Fiakpui

George Thomas

Andhe V Narender Reddy

Sameeh M Salama

Rajeshwar Singh

Original Assignee

Pantherix Ltd

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.)

2000-09-14

Filing date

2001-09-14

Publication date

2003-09-11

2001-09-14 Application filed by Pantherix Ltd filed Critical Pantherix Ltd

2003-09-11 Publication of SK2462003A3 publication Critical patent/SK2462003A3/sk

Links

239000003242 anti bacterial agent Substances 0.000 title description 9
230000003287 optical effect Effects 0.000 claims abstract description 12
150000001875 compounds Chemical class 0.000 claims description 54
-1 2,5-dihydroxy-4-oxo-1,4-dihydropyridin-2-ylcarbonyl Chemical group 0.000 claims description 20
239000000203 mixture Substances 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 13
239000000243 solution Substances 0.000 claims description 13
238000000034 method Methods 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 8
239000007924 injection Substances 0.000 claims description 8
238000002347 injection Methods 0.000 claims description 8
150000001768 cations Chemical class 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
208000035143 Bacterial infection Diseases 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
208000022362 bacterial infectious disease Diseases 0.000 claims description 6
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
NSRVGDULUQOEBX-UHFFFAOYSA-N 3-amino-2-oxoazetidine-1-sulfonic acid Chemical compound NC1CN(S(O)(=O)=O)C1=O NSRVGDULUQOEBX-UHFFFAOYSA-N 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 5
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125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
239000000829 suppository Substances 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
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150000002367 halogens Chemical class 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
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239000008194 pharmaceutical composition Substances 0.000 claims description 3
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
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125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
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239000003937 drug carrier Substances 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
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239000011737 fluorine Substances 0.000 claims description 2
239000008103 glucose Substances 0.000 claims description 2
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000006239 protecting group Chemical group 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
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125000001841 imino group Chemical group [H]N=* 0.000 description 25
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
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238000005481 NMR spectroscopy Methods 0.000 description 7
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RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
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GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
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 5
238000006243 chemical reaction Methods 0.000 description 5
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VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
239000000376 reactant Substances 0.000 description 4
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
206010034133 Pathogen resistance Diseases 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
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FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 3
239000012528 membrane Substances 0.000 description 3
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ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
KEGFZKKQEBALIJ-UHFFFAOYSA-N 3,4-dihydroxy-1h-pyridin-2-one Chemical group OC=1C=CNC(=O)C=1O KEGFZKKQEBALIJ-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
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HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
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229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical group COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
229940041009 monobactams Drugs 0.000 description 1
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CIAOJLKEFVPKRX-UHFFFAOYSA-N octadecapotassium;fluoro(dioxido)borane Chemical compound [K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[O-]B([O-])F.[O-]B([O-])F.[O-]B([O-])F.[O-]B([O-])F.[O-]B([O-])F.[O-]B([O-])F.[O-]B([O-])F.[O-]B([O-])F.[O-]B([O-])F CIAOJLKEFVPKRX-UHFFFAOYSA-N 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
239000003002 pH adjusting agent Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
244000052769 pathogen Species 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical compound OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000004208 shellac Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
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UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide-pyridine complex Substances O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
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235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
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DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000005271 tributylamino group Chemical group 0.000 description 1
229940126085 β‑Lactamase Inhibitor Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
- 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
- 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
- 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

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SK246-2003A 2000-09-14 2001-09-14 3-(Heteroaryl acetamido)-2-oxo-azetidine-1-sulfonic acids derivatives as antibacterial agents SK2462003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US23261700P	2000-09-14	2000-09-14
PCT/IB2001/002115 WO2002022613A1 (en)	2000-09-14	2001-09-14	3-(heteroaryl acetamido)-2-oxo-azetidine-1-sulfonic acids derivatives as antibacterial agents

Publications (1)

Publication Number	Publication Date
SK2462003A3 true SK2462003A3 (en)	2003-09-11

Family

ID=22873854

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK246-2003A SK2462003A3 (en)	2000-09-14	2001-09-14	3-(Heteroaryl acetamido)-2-oxo-azetidine-1-sulfonic acids derivatives as antibacterial agents

Country Status (23)

Country	Link
US (1)	US6916803B2 (xx)
EP (1)	EP1322648B1 (xx)
JP (1)	JP2004509122A (xx)
KR (1)	KR100854810B1 (xx)
CN (1)	CN1189469C (xx)
AT (1)	ATE298750T1 (xx)
AU (2)	AU2002212614B2 (xx)
BR (1)	BR0113861A (xx)
CA (1)	CA2422375C (xx)
CZ (1)	CZ304586B6 (xx)
DE (1)	DE60111757T2 (xx)
DK (1)	DK1322648T3 (xx)
ES (1)	ES2244666T3 (xx)
HK (1)	HK1054377A1 (xx)
HU (1)	HUP0301025A3 (xx)
IL (2)	IL154593A0 (xx)
NO (1)	NO324946B1 (xx)
NZ (1)	NZ524292A (xx)
PL (1)	PL218196B1 (xx)
PT (1)	PT1322648E (xx)
SK (1)	SK2462003A3 (xx)
WO (1)	WO2002022613A1 (xx)
ZA (1)	ZA200302085B (xx)

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US9012491B2 (en)	2011-08-31	2015-04-21	Rempex Pharmaceuticals, Inc.	Heterocyclic boronic acid ester derivatives and therapeutic uses thereof
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US9156858B2 (en)	2012-05-23	2015-10-13	Rempex Pharmaceuticals, Inc.	Boronic acid derivatives and therapeutic uses thereof
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CN102757405B (zh) *	2012-07-25	2014-04-16	山东理工大学	含噻二唑的香兰素衍生物、其制备方法及其用途
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EA201591004A1 (ru)	2013-01-04	2016-02-29	Ремпекс Фармасьютикалз, Инк.	Производные бороновой кислоты и их терапевтическое применение
US9101638B2 (en)	2013-01-04	2015-08-11	Rempex Pharmaceuticals, Inc.	Boronic acid derivatives and therapeutic uses thereof
CA2894891A1 (en)	2013-01-04	2014-07-10	Rempex Pharmaceuticals, Inc.	Boronic acid derivatives and therapeutic uses thereof
RS59488B1 (sr)	2014-05-05	2019-12-31	Rempex Pharmaceuticals Inc	Sinteza boronatnih soli i njihove upotrebe
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MX2016015093A (es)	2014-05-19	2017-03-27	Rempex Pharmaceuticals Inc	Derivados de acido boronico y sus usos terapeuticos.
EA201692301A1 (ru)	2014-07-01	2017-06-30	Ремпекс Фармасьютикалз, Инк.	Производные бороновой кислоты и их терапевтическое применение
US10662205B2 (en)	2014-11-18	2020-05-26	Qpex Biopharma, Inc.	Cyclic boronic acid ester derivatives and therapeutic uses thereof
US10364257B2 (en)	2014-12-19	2019-07-30	Rempex Pharmaceuticals, Inc.	Apparatus and continuous flow process for production of boronic acid derivatives
WO2016149393A1 (en)	2015-03-17	2016-09-22	Rempex Pharmaceuticals, Inc.	Boronic acid derivatives and therapeutic uses thereof
BR112018077015B1 (pt)	2016-06-30	2022-05-03	Qpex Biopharma, Inc	Derivados de ácido borônico e usos terapêuticos dos mesmos
CN107641119B (zh) *	2016-07-21	2019-11-08	中国科学院上海药物研究所	单环β-内酰胺-铁载体轭合物及其制备方法和用途
MA47110A (fr)	2016-12-21	2019-10-30	Aicuris Gmbh & Co Kg	Polythérapie avec des composés de ss-lactame substitués par amidine et des inhibiteurs de ss-lactamase pour des infections par des souches bactériennes résistantes aux antibiotiques
BR112020007138B1 (pt)	2017-10-11	2023-03-21	Qpex Biopharma, Inc	Derivados de ácido borônico, métodos de síntese, composição farmacêutica e uso dos mesmos
WO2019144969A1 (zh)	2018-01-29	2019-08-01	南京明德新药研发股份有限公司	用于治疗细菌感染的单环β-内酰胺化合物
EP3781576B1 (en)	2018-04-20	2024-06-12	Qpex Biopharma, Inc.	Boronic acid derivatives and therapeutic uses thereof
JP7179185B2 (ja)	2018-12-18	2022-11-28	メッドシャインディスカバリーインコーポレイテッド	医薬の製造おける単環式β－ラクタム化合物の使用
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US11040987B2 (en)	2019-09-11	2021-06-22	Tennor Therapeutics Limited	Penam derivatives for treating bacterial infections
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EP4079305A4 (en)	2019-12-19	2024-01-10	Shenzhen Optimum Biological Technology Co., Ltd	APPLICATION OF A COMPOUND IN THE PREPARATION OF DRUG
CN113754651B (zh) *	2020-06-02	2023-04-18	中国医学科学院医药生物技术研究所	一种β-内酰胺化合物、其用途及其制备方法
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2001
- 2001-09-14 CN CNB018157319A patent/CN1189469C/zh not_active Expired - Fee Related
- 2001-09-14 ES ES01980829T patent/ES2244666T3/es not_active Expired - Lifetime
- 2001-09-14 AT AT01980829T patent/ATE298750T1/de active
- 2001-09-14 PL PL360537A patent/PL218196B1/pl unknown
- 2001-09-14 US US10/363,222 patent/US6916803B2/en not_active Expired - Fee Related
- 2001-09-14 IL IL15459301A patent/IL154593A0/xx active IP Right Grant
- 2001-09-14 CZ CZ2003-606A patent/CZ304586B6/cs not_active IP Right Cessation
- 2001-09-14 HU HU0301025A patent/HUP0301025A3/hu unknown
- 2001-09-14 DE DE60111757T patent/DE60111757T2/de not_active Expired - Lifetime
- 2001-09-14 SK SK246-2003A patent/SK2462003A3/sk unknown
- 2001-09-14 KR KR1020037003718A patent/KR100854810B1/ko not_active IP Right Cessation
- 2001-09-14 BR BR0113861-8A patent/BR0113861A/pt active Search and Examination
- 2001-09-14 PT PT01980829T patent/PT1322648E/pt unknown
- 2001-09-14 JP JP2002526866A patent/JP2004509122A/ja active Pending
- 2001-09-14 NZ NZ524292A patent/NZ524292A/en unknown
- 2001-09-14 ZA ZA200302085A patent/ZA200302085B/en unknown
- 2001-09-14 CA CA2422375A patent/CA2422375C/en not_active Expired - Fee Related
- 2001-09-14 AU AU2002212614A patent/AU2002212614B2/en not_active Ceased
- 2001-09-14 AU AU1261402A patent/AU1261402A/xx active Pending
- 2001-09-14 WO PCT/IB2001/002115 patent/WO2002022613A1/en active IP Right Grant
- 2001-09-14 EP EP01980829A patent/EP1322648B1/en not_active Expired - Lifetime
- 2001-09-14 DK DK01980829T patent/DK1322648T3/da active
2003
- 2003-02-24 IL IL154593A patent/IL154593A/en not_active IP Right Cessation
- 2003-03-13 NO NO20031162A patent/NO324946B1/no not_active IP Right Cessation
- 2003-09-03 HK HK03106287A patent/HK1054377A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
DE60111757D1 (de)	2005-08-04
US6916803B2 (en)	2005-07-12
US20040019203A1 (en)	2004-01-29
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