CA2815821C - Monobactams useful for treating bacterial infections - Google Patents
Monobactams useful for treating bacterial infections Download PDFInfo
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- CA2815821C CA2815821C CA2815821A CA2815821A CA2815821C CA 2815821 C CA2815821 C CA 2815821C CA 2815821 A CA2815821 A CA 2815821A CA 2815821 A CA2815821 A CA 2815821A CA 2815821 C CA2815821 C CA 2815821C
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- 208000035143 Bacterial infection Diseases 0.000 title claims abstract description 15
- 208000022362 bacterial infectious disease Diseases 0.000 title claims abstract description 15
- 229940041009 monobactams Drugs 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims description 225
- 229910052739 hydrogen Inorganic materials 0.000 claims description 96
- 239000001257 hydrogen Substances 0.000 claims description 96
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 81
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 65
- 229910052799 carbon Inorganic materials 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 239000003814 drug Substances 0.000 claims description 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 13
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 13
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 9
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 8
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- JLNPLWTWFIPBPD-IINYFYTJSA-N 2-[[1-(2-amino-1,3-thiazol-4-yl)-2-[[(2S,3R)-2-[[(1,5-dihydroxy-4-oxopyridin-2-yl)methylcarbamoylamino]methyl]-4-oxo-1-sulfoazetidin-3-yl]amino]-2-oxoethylidene]amino]oxy-2-methylpropanoic acid Chemical compound C([C@H]1[C@H](C(N1S(O)(=O)=O)=O)NC(=O)C(=NOC(C)(C)C(O)=O)C=1N=C(N)SC=1)NC(=O)NCC1=CC(=O)C(O)=CN1O JLNPLWTWFIPBPD-IINYFYTJSA-N 0.000 claims 1
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- KHVCOYGKHDJPBZ-WDCZJNDASA-N tetrahydrooxazine Chemical compound OC[C@H]1ONC[C@@H](O)[C@@H]1O KHVCOYGKHDJPBZ-WDCZJNDASA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229960004089 tigecycline Drugs 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 238000003354 tissue distribution assay Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000002132 β-lactam antibiotic Substances 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
- 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
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41757510P | 2010-11-29 | 2010-11-29 | |
| US61/417,575 | 2010-11-29 | ||
| PCT/IB2011/055104 WO2012073138A1 (en) | 2010-11-29 | 2011-11-15 | Monobactams |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2815821A1 CA2815821A1 (en) | 2012-06-07 |
| CA2815821C true CA2815821C (en) | 2015-07-07 |
Family
ID=45315854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2815821A Expired - Fee Related CA2815821C (en) | 2010-11-29 | 2011-11-15 | Monobactams useful for treating bacterial infections |
Country Status (17)
| Country | Link |
|---|---|
| US (3) | US20120302542A1 (enExample) |
| EP (1) | EP2646436B1 (enExample) |
| JP (1) | JP5777725B2 (enExample) |
| KR (1) | KR101514587B1 (enExample) |
| CN (1) | CN103228652B (enExample) |
| AR (1) | AR084001A1 (enExample) |
| AU (1) | AU2011336209B2 (enExample) |
| CA (1) | CA2815821C (enExample) |
| DK (1) | DK2646436T3 (enExample) |
| ES (1) | ES2542431T3 (enExample) |
| IL (1) | IL226052A0 (enExample) |
| MX (1) | MX2013005994A (enExample) |
| SG (1) | SG190007A1 (enExample) |
| TW (1) | TW201247661A (enExample) |
| UY (1) | UY33754A (enExample) |
| WO (1) | WO2012073138A1 (enExample) |
| ZA (1) | ZA201304479B (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9988373B2 (en) | 2013-12-26 | 2018-06-05 | Shionogi & Co., Ltd. | Nitrogen-containing six-membered cyclic derivatives and pharmaceutical composition comprising the same |
| MA39777B1 (fr) | 2014-03-24 | 2019-03-29 | Novartis Ag | Composes organiques de la famille des monobactams pour le traitement d'infections bactériennes |
| RU2754180C2 (ru) * | 2015-09-23 | 2021-08-30 | Новартис Аг | Соли и твердые формы монобактамного антибиотика |
| CN105481812B (zh) * | 2015-11-30 | 2020-04-21 | 重庆天奕恒化科技有限公司 | 一种5-苄氧基-4-氧代-4h-吡喃-2-羧酸的制备方法 |
| EP3390357B1 (en) * | 2015-12-15 | 2021-11-10 | Merck Sharp & Dohme Corp. | Biaryl monobactam compounds for the treatment of bacterial infections |
| KR102408800B1 (ko) | 2016-03-07 | 2022-06-13 | 머크 샤프 앤드 돔 코포레이션 | 비시클릭 아릴 모노박탐 화합물 및 박테리아 감염의 치료를 위한 그의 사용 방법 |
| US10047077B2 (en) | 2016-04-13 | 2018-08-14 | Skyline Antiinfectives, Inc. | Deuterated O-sulfated beta-lactam hydroxamic acids and deuterated N-sulfated beta-lactams |
| 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 |
| JP7235718B2 (ja) | 2017-08-02 | 2023-03-08 | ノバルティス アーゲー | モノバクタム系抗生物質およびその中間体を製造するための化学的方法 |
| KR102425959B1 (ko) | 2017-10-02 | 2022-07-27 | 머크 샤프 앤드 돔 코포레이션 | 박테리아 감염의 치료를 위한 크로만 모노박탐 화합물 |
| US10513504B2 (en) | 2018-03-08 | 2019-12-24 | Apotex Inc. | Processes for the preparation of apalutamide and intermediates thereof |
| US12516049B2 (en) | 2019-11-22 | 2026-01-06 | Suzhou Erye Pharmaceutical Co., Ltd | Sulfonylurea ring substituted monocyclic β-lactam antibiotics |
| FI4069691T3 (fi) | 2019-12-06 | 2024-11-13 | Vertex Pharma | Substituoituja tetrahydrofuraaneja natriumkanavien modulaattoreina |
| CN111303144B (zh) * | 2019-12-13 | 2020-11-27 | 苏州信诺维医药科技有限公司 | 一种治疗细菌感染的化合物 |
| AU2022250095B2 (en) | 2021-03-31 | 2023-11-23 | Fedora Pharmaceuticals Inc. | Lactivicin compounds, their preparation and use as antibacterial agents |
| US12528804B2 (en) | 2021-03-31 | 2026-01-20 | Fedora Pharmaceuticals Inc. | Lactivicin compounds, their preparation and use as antibacterial agents |
| WO2022235077A1 (ko) * | 2021-05-07 | 2022-11-10 | 한국생명공학연구원 | 신규 사이드로포어 화합물 및 이를 이용한 금속 나노입자 복합체 |
| CR20230586A (es) | 2021-06-04 | 2024-05-07 | Vertex Pharma | N-(hydroxyalquil (hetero)aril) tetrahidrofurano carboxamidas como moduladores de canales de sodio |
| AU2022391635B2 (en) | 2021-11-18 | 2025-10-02 | Merck Sharp & Dohme Llc | Chromane amidine monobactam antibiotics |
| JP7671398B2 (ja) * | 2021-11-18 | 2025-05-01 | メルク・シャープ・アンド・ドーム・エルエルシー | クロマンアミジンモノバクタム抗生物質 |
| JP2025513455A (ja) | 2022-04-22 | 2025-04-24 | バーテックス ファーマシューティカルズ インコーポレイテッド | 疼痛の治療のためのヘテロアリール化合物 |
| CN115304594B (zh) * | 2022-10-12 | 2023-02-14 | 苏州二叶制药有限公司 | 磺酰脲环取代的化合物的盐型及其晶型 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR880701238A (ko) * | 1986-05-23 | 1988-07-26 | 로버트 에이 아르미티즈 | N-1 치환 설포닐아미노카르보닐,c-4 치환 모노박탐 |
| SI1965798T1 (sl) | 2005-12-07 | 2012-01-31 | Basilea Pharmaceutica Ag | Uporabni monobaktamski antibiotiki |
| AU2008232262B2 (en) | 2007-03-28 | 2013-02-14 | Apotex Inc. | Fluorinated derivatives of deferiprone |
| MX2011006541A (es) * | 2008-12-19 | 2011-07-20 | Pfizer | Monocarbamas. |
-
2011
- 2011-11-15 ES ES11794237.5T patent/ES2542431T3/es active Active
- 2011-11-15 SG SG2013031752A patent/SG190007A1/en unknown
- 2011-11-15 KR KR1020137016718A patent/KR101514587B1/ko not_active Expired - Fee Related
- 2011-11-15 CA CA2815821A patent/CA2815821C/en not_active Expired - Fee Related
- 2011-11-15 MX MX2013005994A patent/MX2013005994A/es active IP Right Grant
- 2011-11-15 AU AU2011336209A patent/AU2011336209B2/en not_active Ceased
- 2011-11-15 DK DK11794237.5T patent/DK2646436T3/en active
- 2011-11-15 CN CN201180057264.5A patent/CN103228652B/zh not_active Expired - Fee Related
- 2011-11-15 WO PCT/IB2011/055104 patent/WO2012073138A1/en not_active Ceased
- 2011-11-15 JP JP2013541445A patent/JP5777725B2/ja not_active Expired - Fee Related
- 2011-11-15 EP EP11794237.5A patent/EP2646436B1/en not_active Not-in-force
- 2011-11-24 TW TW100143172A patent/TW201247661A/zh unknown
- 2011-11-25 AR ARP110104404A patent/AR084001A1/es not_active Application Discontinuation
- 2011-11-28 UY UY0001033754A patent/UY33754A/es not_active Application Discontinuation
- 2011-11-29 US US13/306,581 patent/US20120302542A1/en not_active Abandoned
-
2013
- 2013-02-27 US US13/778,670 patent/US20130252935A1/en not_active Abandoned
- 2013-04-29 IL IL226052A patent/IL226052A0/en unknown
- 2013-06-18 ZA ZA2013/04479A patent/ZA201304479B/en unknown
-
2015
- 2015-01-29 US US14/608,826 patent/US20150148326A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| HK1184462A1 (en) | 2014-01-24 |
| IL226052A0 (en) | 2013-06-27 |
| MX2013005994A (es) | 2013-07-15 |
| KR20130112054A (ko) | 2013-10-11 |
| EP2646436A1 (en) | 2013-10-09 |
| AU2011336209B2 (en) | 2015-03-19 |
| AR084001A1 (es) | 2013-04-17 |
| JP2013544276A (ja) | 2013-12-12 |
| DK2646436T3 (en) | 2015-06-29 |
| WO2012073138A1 (en) | 2012-06-07 |
| JP5777725B2 (ja) | 2015-09-09 |
| CN103228652A (zh) | 2013-07-31 |
| SG190007A1 (en) | 2013-06-28 |
| TW201247661A (en) | 2012-12-01 |
| ES2542431T3 (es) | 2015-08-05 |
| UY33754A (es) | 2012-06-29 |
| AU2011336209A1 (en) | 2013-05-30 |
| EP2646436B1 (en) | 2015-05-27 |
| US20150148326A1 (en) | 2015-05-28 |
| KR101514587B1 (ko) | 2015-04-22 |
| US20120302542A1 (en) | 2012-11-29 |
| ZA201304479B (en) | 2014-03-26 |
| CN103228652B (zh) | 2015-02-18 |
| CA2815821A1 (en) | 2012-06-07 |
| US20130252935A1 (en) | 2013-09-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20130424 |
|
| MKLA | Lapsed |
Effective date: 20171115 |