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)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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 (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015099107A1 (ja) | 2013-12-26 | 2015-07-02 | 塩野義製薬株式会社 | 含窒素６員環誘導体およびそれらを含有する医薬組成物 |
| SMT201900218T1 (it) | 2014-03-24 | 2019-05-10 | Novartis Ag | Composti organici di monobattami, per il trattamento di infezioni batteriche |
| EA037569B1 (ru) | 2015-09-23 | 2021-04-15 | Новартис Аг | Соли монобактамного антибиотика и их применение |
| 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 |
| KR20180093925A (ko) * | 2015-12-15 | 2018-08-22 | 머크 샤프 앤드 돔 코포레이션 | 박테리아 감염을 치료하기 위한 비아릴 모노박탐 화합물 및 그의 사용 방법 |
| CN108778273B (zh) | 2016-03-07 | 2022-06-17 | 默沙东公司 | 二环芳基单环β-内酰胺化合物及其用于治疗细菌感染的用途的方法 |
| 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 |
| US11414411B2 (en) | 2017-08-02 | 2022-08-16 | Novartis Ag | Chemical process for manufacturing monobactam antibiotic and intermediates thereof |
| CN111201021B (zh) | 2017-10-02 | 2024-08-23 | 默沙东有限责任公司 | 用于治疗细菌感染的苯并二氢吡喃单环β-内酰胺类化合物 |
| US10513504B2 (en) | 2018-03-08 | 2019-12-24 | Apotex Inc. | Processes for the preparation of apalutamide and intermediates thereof |
| KR102786898B1 (ko) * | 2019-11-22 | 2025-03-25 | 쑤저우 얼예 파마슈티칼 컴퍼니 리미티드 | 설포닐우레아 고리 치환 모노시클릭 β-락탐계 항생제 |
| DK4069691T3 (da) | 2019-12-06 | 2024-10-28 | Vertex Pharma | Substituerede tetrahydrofuraner som modulatorer af natriumkanaler |
| 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 |
| MX2023011616A (es) | 2021-03-31 | 2023-10-30 | Fedora Pharmaceuticals Inc | Compuestos de lactivicina, su preparacion y uso como agentes antibacterianos. |
| KR102781293B1 (ko) * | 2021-05-07 | 2025-03-17 | 한국생명공학연구원 | 신규 사이드로포어 화합물 및 이를 이용한 금속 나노입자 복합체 |
| US11827627B2 (en) | 2021-06-04 | 2023-11-28 | Vertex Pharmaceuticals Incorporated | N-(hydroxyalkyl (hetero)aryl) tetrahydrofuran carboxamides as modulators of sodium channels |
| TWI829432B (zh) | 2021-11-18 | 2024-01-11 | 美商默沙東有限責任公司 | 用於治療細菌感染之唍脒單環內醯胺（ｍｏｎｏｂａｃｔａｍ）化合物 |
| 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 |
| WO2023205463A1 (en) | 2022-04-22 | 2023-10-26 | Vertex Pharmaceuticals Incorporated | Heteroaryl compounds for the treatment of pain |
| 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 |
|---|---|---|---|---|
| JPH01502660A (ja) * | 1986-05-23 | 1989-09-14 | ジ・アップジョン・カンパニー | Ｎ―１置換スルホニルアミノカルボニル、ｃ―４置換モノバクタム類 |
| CA2629570C (en) | 2005-12-07 | 2012-11-27 | Basilea Pharmaceutica Ag | Useful combinations of monobactam antibiotics with beta-lactamase inhibitors |
| MX2009010407A (es) | 2007-03-28 | 2009-12-01 | Apotex Technologies Inc | Derivados fluorados de deferiprona. |
| EP2379546A1 (en) * | 2008-12-19 | 2011-10-26 | Pfizer Inc. | Monocarbams |
-
2011
- 2011-11-15 EP EP11794237.5A patent/EP2646436B1/en not_active Not-in-force
- 2011-11-15 KR KR1020137016718A patent/KR101514587B1/ko not_active Expired - Fee Related
- 2011-11-15 CN CN201180057264.5A patent/CN103228652B/zh not_active Expired - Fee Related
- 2011-11-15 MX MX2013005994A patent/MX2013005994A/es active IP Right Grant
- 2011-11-15 CA CA2815821A patent/CA2815821C/en not_active Expired - Fee Related
- 2011-11-15 ES ES11794237.5T patent/ES2542431T3/es active Active
- 2011-11-15 DK DK11794237.5T patent/DK2646436T3/en active
- 2011-11-15 AU AU2011336209A patent/AU2011336209B2/en not_active Ceased
- 2011-11-15 SG SG2013031752A patent/SG190007A1/en unknown
- 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
- 2011-11-24 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 |
|---|---|
| JP2013544276A (ja) | 2013-12-12 |
| ES2542431T3 (es) | 2015-08-05 |
| CA2815821A1 (en) | 2012-06-07 |
| AU2011336209B2 (en) | 2015-03-19 |
| HK1184462A1 (en) | 2014-01-24 |
| UY33754A (es) | 2012-06-29 |
| CN103228652B (zh) | 2015-02-18 |
| EP2646436A1 (en) | 2013-10-09 |
| CN103228652A (zh) | 2013-07-31 |
| KR20130112054A (ko) | 2013-10-11 |
| EP2646436B1 (en) | 2015-05-27 |
| ZA201304479B (en) | 2014-03-26 |
| WO2012073138A1 (en) | 2012-06-07 |
| KR101514587B1 (ko) | 2015-04-22 |
| IL226052A0 (en) | 2013-06-27 |
| AU2011336209A1 (en) | 2013-05-30 |
| DK2646436T3 (en) | 2015-06-29 |
| MX2013005994A (es) | 2013-07-15 |
| US20150148326A1 (en) | 2015-05-28 |
| JP5777725B2 (ja) | 2015-09-09 |
| AR084001A1 (es) | 2013-04-17 |
| US20120302542A1 (en) | 2012-11-29 |
| SG190007A1 (en) | 2013-06-28 |
| US20130252935A1 (en) | 2013-09-26 |
| TW201247661A (en) | 2012-12-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20130424 |
|
| MKLA | Lapsed |
Effective date: 20171115 |