KR20130105659A - 광범위 스펙트럼 항생제 아릴로마이신 유사체 - Google Patents
광범위 스펙트럼 항생제 아릴로마이신 유사체 Download PDFInfo
- Publication number
- KR20130105659A KR20130105659A KR1020137009510A KR20137009510A KR20130105659A KR 20130105659 A KR20130105659 A KR 20130105659A KR 1020137009510 A KR1020137009510 A KR 1020137009510A KR 20137009510 A KR20137009510 A KR 20137009510A KR 20130105659 A KR20130105659 A KR 20130105659A
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- KR
- South Korea
- Prior art keywords
- alkyl
- staphylococcus
- aryl
- arylomycin
- groups
- Prior art date
- 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.)
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- 230000003115 biocidal effect Effects 0.000 title claims abstract description 22
- 108010087967 type I signal peptidase Proteins 0.000 claims abstract description 229
- 238000000034 method Methods 0.000 claims abstract description 134
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- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 35
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 30
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- 229940088710 antibiotic agent Drugs 0.000 claims abstract description 25
- 238000011282 treatment Methods 0.000 claims abstract description 25
- YFSXYWAZCKMYJN-JBBOGOJTSA-N chembl1231055 Chemical compound C=1C=C(O)C2=CC=1C[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N(C)C(=O)CNC(=O)[C@@H](C)NC(=O)[C@@H](CO)N(C)C(=O)CCCCCCCCC(C)C)C1=CC=C(O)C2=C1 YFSXYWAZCKMYJN-JBBOGOJTSA-N 0.000 claims abstract description 10
- 108010047091 arylomycin A2 Proteins 0.000 claims abstract description 7
- YFSXYWAZCKMYJN-UHFFFAOYSA-N arylomycin A2 Natural products C=1C=C(O)C2=CC=1CC(C(O)=O)NC(=O)C(C)NC(=O)C(N(C)C(=O)CNC(=O)C(C)NC(=O)C(CO)N(C)C(=O)CCCCCCCCC(C)C)C1=CC=C(O)C2=C1 YFSXYWAZCKMYJN-UHFFFAOYSA-N 0.000 claims abstract description 7
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- 125000003118 aryl group Chemical group 0.000 claims description 96
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 80
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- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 55
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- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 48
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 47
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 46
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- 125000004429 atom Chemical group 0.000 claims description 44
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- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- 125000005842 heteroatom Chemical group 0.000 claims description 28
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 27
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- 238000009396 hybridization Methods 0.000 claims description 26
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 21
- 125000001153 fluoro group Chemical group F* 0.000 claims description 20
- 125000002950 monocyclic group Chemical group 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 125000004122 cyclic group Chemical group 0.000 claims description 18
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical group NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
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- 238000001514 detection method Methods 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 16
- JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims description 16
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 15
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 15
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- 150000001721 carbon Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
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- 125000004001 thioalkyl group Chemical group 0.000 claims description 12
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- 238000006467 substitution reaction Methods 0.000 claims description 11
- 150000001408 amides Chemical group 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 244000005700 microbiome Species 0.000 claims description 10
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 9
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
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- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 241000194025 Streptococcus oralis Species 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
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- 239000012453 solvate Substances 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
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- 125000006413 ring segment Chemical group 0.000 claims description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
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- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
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Classifications
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- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- C07K9/001—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence having less than 12 amino acids and not being part of a ring structure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- 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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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Immunology (AREA)
- Gastroenterology & Hepatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Enzymes And Modification Thereof (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38298810P | 2010-09-15 | 2010-09-15 | |
| US61/382,988 | 2010-09-15 | ||
| PCT/US2011/049967 WO2012036907A2 (en) | 2010-09-15 | 2011-08-31 | Broad spectrum antibiotic arylomycin analogs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20130105659A true KR20130105659A (ko) | 2013-09-25 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020137009510A Withdrawn KR20130105659A (ko) | 2010-09-15 | 2011-08-31 | 광범위 스펙트럼 항생제 아릴로마이신 유사체 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9187524B2 (https=) |
| EP (1) | EP2616093A4 (https=) |
| JP (1) | JP2013539751A (https=) |
| KR (1) | KR20130105659A (https=) |
| CN (1) | CN103209700A (https=) |
| BR (1) | BR112013006265A2 (https=) |
| CA (1) | CA2811295A1 (https=) |
| MX (1) | MX2013003035A (https=) |
| RU (1) | RU2013112483A (https=) |
| WO (1) | WO2012036907A2 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112013006265A2 (pt) | 2010-09-15 | 2016-06-07 | Scripps Research Inst | espectros antibióticos gerais análogos a arilomicina |
| US10501493B2 (en) | 2011-05-27 | 2019-12-10 | Rqx Pharmaceuticals, Inc. | Broad spectrum antibiotics |
| TWI642684B (zh) * | 2011-05-27 | 2018-12-01 | Ｒｑｘ製藥股份有限公司 | 廣效性抗生素 |
| CA2867448A1 (en) * | 2012-03-14 | 2013-09-19 | Floyd E. Romesberg | Broad spectrum antibiotic arylomycin analogs |
| KR20150088292A (ko) * | 2012-11-21 | 2015-07-31 | 알큐엑스 파마슈티컬스, 인크. | 광범위한 마크로사이클릭 항생제 |
| CN103103261A (zh) * | 2013-01-05 | 2013-05-15 | 张国新 | 检测幽门螺杆菌对克拉霉素耐药性试剂盒及制备方法 |
| WO2015179441A2 (en) * | 2014-05-20 | 2015-11-26 | Rqx Pharmaceuticals, Inc. | Macrocyclic broad spectrum antibiotics |
| AU2015339039B2 (en) * | 2014-10-31 | 2019-11-28 | Temple University -- Of The Commonwealth System Of Higher Education | Synergistic compositions for treating microbial infections |
| US11072635B2 (en) | 2015-11-20 | 2021-07-27 | Rqx Pharmaceuticals, Inc. | Macrocyclic broad spectrum antibiotics |
| WO2017214534A1 (en) | 2016-06-10 | 2017-12-14 | The Scripps Research Institute | Synthesis of the arylomycin macrocyclic core |
| AU2018222093B2 (en) * | 2017-02-15 | 2022-03-31 | Genentech, Inc. | Macrocyclic broad spectrum antibiotics |
| EP3388445A1 (en) * | 2017-04-10 | 2018-10-17 | F. Hoffmann-La Roche AG | Peptide macrocycles and use thereof in the treatment of bacterial infections |
| JP7078807B2 (ja) | 2019-05-28 | 2022-05-31 | エフ．ホフマン－ラ ロシュ アーゲー | 大環状広域スペクトル抗生物質 |
| CN116023430B (zh) * | 2022-12-20 | 2025-11-25 | 中国药科大学 | 2-(2-(2-苯甲酰氨基)乙酰胺)苯甲酸类衍生物及其制备方法和用途 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0862638A1 (en) * | 1995-11-03 | 1998-09-09 | E.I. Du Pont De Nemours And Company | Positive selection vector for bacillus sp. |
| US6951840B2 (en) * | 2001-08-31 | 2005-10-04 | Eli Lilly And Company | Lipoglycopeptide antibiotics |
| DE102005014245A1 (de) | 2005-03-30 | 2006-10-05 | Aicuris Gmbh & Co. Kg | Antibakterielle Amid-Makrozyklen V |
| CN102939095A (zh) | 2010-03-09 | 2013-02-20 | 默沙东公司 | 增强β-内酰胺抗菌药物的活性的桥联脂糖肽类 |
| BR112013006265A2 (pt) | 2010-09-15 | 2016-06-07 | Scripps Research Inst | espectros antibióticos gerais análogos a arilomicina |
| TWI642684B (zh) * | 2011-05-27 | 2018-12-01 | Ｒｑｘ製藥股份有限公司 | 廣效性抗生素 |
| CA2867448A1 (en) | 2012-03-14 | 2013-09-19 | Floyd E. Romesberg | Broad spectrum antibiotic arylomycin analogs |
-
2011
- 2011-08-31 BR BR112013006265A patent/BR112013006265A2/pt not_active IP Right Cessation
- 2011-08-31 RU RU2013112483/04A patent/RU2013112483A/ru not_active Application Discontinuation
- 2011-08-31 WO PCT/US2011/049967 patent/WO2012036907A2/en not_active Ceased
- 2011-08-31 EP EP11825668.4A patent/EP2616093A4/en not_active Withdrawn
- 2011-08-31 US US13/821,195 patent/US9187524B2/en not_active Expired - Fee Related
- 2011-08-31 JP JP2013529181A patent/JP2013539751A/ja not_active Ceased
- 2011-08-31 CA CA2811295A patent/CA2811295A1/en not_active Abandoned
- 2011-08-31 MX MX2013003035A patent/MX2013003035A/es not_active Application Discontinuation
- 2011-08-31 KR KR1020137009510A patent/KR20130105659A/ko not_active Withdrawn
- 2011-08-31 CN CN2011800550186A patent/CN103209700A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA2811295A1 (en) | 2012-03-22 |
| US9187524B2 (en) | 2015-11-17 |
| EP2616093A4 (en) | 2014-02-26 |
| WO2012036907A2 (en) | 2012-03-22 |
| BR112013006265A2 (pt) | 2016-06-07 |
| CN103209700A (zh) | 2013-07-17 |
| JP2013539751A (ja) | 2013-10-28 |
| RU2013112483A (ru) | 2014-10-20 |
| EP2616093A2 (en) | 2013-07-24 |
| WO2012036907A3 (en) | 2012-08-09 |
| MX2013003035A (es) | 2013-12-16 |
| US20130281360A1 (en) | 2013-10-24 |
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