JP2004527530A - ペプチドデホルミラーゼ阻害物質 - Google Patents
ペプチドデホルミラーゼ阻害物質 Download PDFInfo
- Publication number
- JP2004527530A JP2004527530A JP2002579414A JP2002579414A JP2004527530A JP 2004527530 A JP2004527530 A JP 2004527530A JP 2002579414 A JP2002579414 A JP 2002579414A JP 2002579414 A JP2002579414 A JP 2002579414A JP 2004527530 A JP2004527530 A JP 2004527530A
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- JP
- Japan
- Prior art keywords
- hydroxyacetamide
- group
- hydroxy
- acetamide
- diiodophenyl
- 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.)
- Pending
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- 239000000081 peptide deformylase inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 150000001408 amides Chemical group 0.000 claims description 6
- 150000001412 amines Chemical group 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- KKTHMPAJCDVKBJ-UHFFFAOYSA-N 2-(3,5-dichloro-4-methoxyphenyl)-n-hydroxyacetamide Chemical compound COC1=C(Cl)C=C(CC(=O)NO)C=C1Cl KKTHMPAJCDVKBJ-UHFFFAOYSA-N 0.000 claims description 4
- SMNAANDQAOLROJ-UHFFFAOYSA-N 2-(3,5-dichloro-4-phenoxyphenyl)-n-hydroxyacetamide Chemical compound ClC1=CC(CC(=O)NO)=CC(Cl)=C1OC1=CC=CC=C1 SMNAANDQAOLROJ-UHFFFAOYSA-N 0.000 claims description 4
- WQMVCLNJMNIZON-UHFFFAOYSA-N 2-(3,5-diiodo-4-phenoxyphenyl)-n-hydroxyacetamide Chemical compound IC1=CC(CC(=O)NO)=CC(I)=C1OC1=CC=CC=C1 WQMVCLNJMNIZON-UHFFFAOYSA-N 0.000 claims description 4
- MWVYYUXWRATDHP-UHFFFAOYSA-N 2-(4-amino-3,5-diiodophenyl)-n-hydroxyacetamide Chemical compound NC1=C(I)C=C(CC(=O)NO)C=C1I MWVYYUXWRATDHP-UHFFFAOYSA-N 0.000 claims description 4
- VQOWOIXHPJYOAJ-UHFFFAOYSA-N 2-[4-[4-[2-(diethylamino)ethoxy]phenoxy]-3,5-diiodophenyl]-n-hydroxyacetamide Chemical compound C1=CC(OCCN(CC)CC)=CC=C1OC1=C(I)C=C(CC(=O)NO)C=C1I VQOWOIXHPJYOAJ-UHFFFAOYSA-N 0.000 claims description 4
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- 150000001735 carboxylic acids Chemical group 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- USLUOOGWHDRFFN-UHFFFAOYSA-N n-hydroxy-2-[4-(4-hydroxyphenoxy)-3,5-diiodophenyl]acetamide Chemical compound IC1=CC(CC(=O)NO)=CC(I)=C1OC1=CC=C(O)C=C1 USLUOOGWHDRFFN-UHFFFAOYSA-N 0.000 claims description 4
- HSIALXIYDPTUSI-UHFFFAOYSA-N n-hydroxy-2-[4-(4-hydroxyphenoxy)-3-iodophenyl]acetamide Chemical compound IC1=CC(CC(=O)NO)=CC=C1OC1=CC=C(O)C=C1 HSIALXIYDPTUSI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- BDBFKEFBGHYVRI-UHFFFAOYSA-N 2-(3,5-diiodo-4-methoxyphenyl)-n-hydroxyacetamide Chemical compound COC1=C(I)C=C(CC(=O)NO)C=C1I BDBFKEFBGHYVRI-UHFFFAOYSA-N 0.000 claims description 3
- SGUQHLKFZZCQGA-UHFFFAOYSA-N 2-(3,5-diiodo-4-phenylmethoxyphenyl)-n-hydroxyacetamide Chemical compound IC1=CC(CC(=O)NO)=CC(I)=C1OCC1=CC=CC=C1 SGUQHLKFZZCQGA-UHFFFAOYSA-N 0.000 claims description 3
- KYJMRQVYZISFBB-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-hydroxyphenyl)-n-hydroxyacetamide Chemical compound CC(C)(C)C1=CC(CC(=O)NO)=CC(C(C)(C)C)=C1O KYJMRQVYZISFBB-UHFFFAOYSA-N 0.000 claims description 3
- XBRDWTYULANWRV-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-methoxyphenyl)-n-hydroxyacetamide Chemical compound COC1=C(C(C)(C)C)C=C(CC(=O)NO)C=C1C(C)(C)C XBRDWTYULANWRV-UHFFFAOYSA-N 0.000 claims description 3
- CDAGXQJXQNAKBU-UHFFFAOYSA-N 2-[3-chloro-4-(cyclopropylmethoxy)phenyl]-n-hydroxyacetamide Chemical compound ClC1=CC(CC(=O)NO)=CC=C1OCC1CC1 CDAGXQJXQNAKBU-UHFFFAOYSA-N 0.000 claims description 3
- CLAPXZCWNKDKFD-UHFFFAOYSA-N 2-[4-(ethylamino)-3,5-diiodophenyl]-n-hydroxyacetamide Chemical compound CCNC1=C(I)C=C(CC(=O)NO)C=C1I CLAPXZCWNKDKFD-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- INFZLXMDXXPQGA-UHFFFAOYSA-N n-hydroxy-2-(3,4,5-trimethoxyphenyl)acetamide Chemical compound COC1=CC(CC(=O)NO)=CC(OC)=C1OC INFZLXMDXXPQGA-UHFFFAOYSA-N 0.000 claims description 3
- UEJPVKVKTCZGFP-UHFFFAOYSA-N n-hydroxy-2-(3-iodo-4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(CC(=O)NO)C=C1I UEJPVKVKTCZGFP-UHFFFAOYSA-N 0.000 claims description 3
- MEBKBOJNQHJGCA-UHFFFAOYSA-N n-hydroxy-2-(4-hydroxy-3,5-diiodophenyl)acetamide Chemical compound ONC(=O)CC1=CC(I)=C(O)C(I)=C1 MEBKBOJNQHJGCA-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 206010057190 Respiratory tract infections Diseases 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
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- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
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- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
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- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 abstract description 3
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- 239000000243 solution Substances 0.000 description 19
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- 150000003839 salts Chemical class 0.000 description 11
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- ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 6
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 5
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- 235000018417 cysteine Nutrition 0.000 description 1
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- AJZKCIXHBRHMKK-UHFFFAOYSA-N ethyl 2-(4-amino-3,5-diiodophenyl)acetate Chemical compound CCOC(=O)CC1=CC(I)=C(N)C(I)=C1 AJZKCIXHBRHMKK-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28161301P | 2001-04-05 | 2001-04-05 | |
| PCT/US2002/010506 WO2002081426A1 (en) | 2001-04-05 | 2002-04-04 | Peptide deformylase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004527530A true JP2004527530A (ja) | 2004-09-09 |
| JP2004527530A5 JP2004527530A5 (enExample) | 2005-12-22 |
Family
ID=23078046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002579414A Pending JP2004527530A (ja) | 2001-04-05 | 2002-04-04 | ペプチドデホルミラーゼ阻害物質 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US20040267015A1 (enExample) |
| EP (1) | EP1383729A4 (enExample) |
| JP (1) | JP2004527530A (enExample) |
| WO (1) | WO2002081426A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012112447A2 (en) * | 2011-02-14 | 2012-08-23 | Dana-Farber Cancer Institute, Inc. | Histone deacetylase inhibitors and methods of use thereof |
| CN109020825B (zh) * | 2017-06-12 | 2021-03-19 | 重庆医科大学 | 抗流感病毒化合物及其制备方法 |
| KR20200128096A (ko) | 2018-03-02 | 2020-11-11 | 오레곤 헬스 앤드 사이언스 유니버시티 | 소분자 핵 수용체 조절제의 아미드 전구약물 |
| AU2019397067A1 (en) | 2018-12-12 | 2021-07-22 | Autobahn Therapeutics, Inc. | Novel thyromimetics |
| AU2020232205A1 (en) | 2019-03-01 | 2021-10-21 | Autobahn Therapeutics, Inc. | Novel thyromimetics |
| US12466781B2 (en) | 2019-11-29 | 2025-11-11 | Autobahn Therapeutics, Inc. | Thyromimetics |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE689347A (enExample) * | 1965-12-09 | 1967-04-14 | Madan Ag | |
| US4052514A (en) * | 1971-03-26 | 1977-10-04 | The Boots Company Limited | Trihalosubstituted biphenylyl propionic acids |
| US4792560A (en) * | 1985-04-03 | 1988-12-20 | Rorer Pharmaceutical Corporation | Quinoline hydroxamates and their use as modulators of arachidonic acid metabolic pathways |
| NO179246C (no) * | 1991-11-20 | 1996-09-04 | Sankyo Co | Aromatiske amino-alkoholderivater og mellomprodukter til fremstilling derav |
| GB9810464D0 (en) * | 1998-05-16 | 1998-07-15 | British Biotech Pharm | Hydroxamic acid derivatives |
| WO2001038561A1 (en) * | 1999-11-29 | 2001-05-31 | Questcor Pharmaceuticals, Inc. | Methods of use of peptide deformylase inhibitors as novel antibacterial agents |
-
2002
- 2002-04-04 WO PCT/US2002/010506 patent/WO2002081426A1/en not_active Ceased
- 2002-04-04 US US10/473,104 patent/US20040267015A1/en not_active Abandoned
- 2002-04-04 EP EP02721667A patent/EP1383729A4/en not_active Withdrawn
- 2002-04-04 JP JP2002579414A patent/JP2004527530A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP1383729A4 (en) | 2006-04-19 |
| US20040267015A1 (en) | 2004-12-30 |
| WO2002081426A1 (en) | 2002-10-17 |
| EP1383729A1 (en) | 2004-01-28 |
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