JP2004531580A5 - - Google Patents
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- Publication number
- JP2004531580A5 JP2004531580A5 JP2003508705A JP2003508705A JP2004531580A5 JP 2004531580 A5 JP2004531580 A5 JP 2004531580A5 JP 2003508705 A JP2003508705 A JP 2003508705A JP 2003508705 A JP2003508705 A JP 2003508705A JP 2004531580 A5 JP2004531580 A5 JP 2004531580A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- formamide
- benzyl
- dichloro
- hydroxyformamide
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 150000001408 amides Chemical group 0.000 claims 4
- 150000001412 amines Chemical group 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 208000035143 Bacterial infection Diseases 0.000 claims 3
- 150000001298 alcohols Chemical group 0.000 claims 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- ZKCSWVNCJKSLPD-UHFFFAOYSA-N n-[(3-chloro-5-methoxy-4-phenoxyphenyl)methyl]-n-hydroxyformamide Chemical compound COC1=CC(CN(O)C=O)=CC(Cl)=C1OC1=CC=CC=C1 ZKCSWVNCJKSLPD-UHFFFAOYSA-N 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 150000001735 carboxylic acids Chemical group 0.000 claims 2
- 150000002170 ethers Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- LWEVMMBCHJTLPP-UHFFFAOYSA-N n-[(3,5-dichloro-4-methoxyphenyl)methyl]-n-hydroxyformamide Chemical compound COC1=C(Cl)C=C(CN(O)C=O)C=C1Cl LWEVMMBCHJTLPP-UHFFFAOYSA-N 0.000 claims 2
- ZFMWABBNBCTDLB-UHFFFAOYSA-N n-[(3,5-dichlorophenyl)methyl]-n-hydroxyformamide Chemical compound O=CN(O)CC1=CC(Cl)=CC(Cl)=C1 ZFMWABBNBCTDLB-UHFFFAOYSA-N 0.000 claims 2
- KEPYVYIXGYQBFB-UHFFFAOYSA-N n-[[3,5-dichloro-4-(2-hydroxyethoxy)phenyl]methyl]-n-hydroxyformamide Chemical compound OCCOC1=C(Cl)C=C(CN(O)C=O)C=C1Cl KEPYVYIXGYQBFB-UHFFFAOYSA-N 0.000 claims 2
- FOBRWHCNQFDXKR-UHFFFAOYSA-N n-[[3,5-dichloro-4-(2-thiophen-2-ylethoxy)phenyl]methyl]-n-hydroxyformamide Chemical compound ClC1=CC(CN(O)C=O)=CC(Cl)=C1OCCC1=CC=CS1 FOBRWHCNQFDXKR-UHFFFAOYSA-N 0.000 claims 2
- NAFAKAITJPWZCX-UHFFFAOYSA-N n-hydroxy-n-[[4-methoxy-3,5-di(propan-2-yl)phenyl]methyl]formamide Chemical compound COC1=C(C(C)C)C=C(CN(O)C=O)C=C1C(C)C NAFAKAITJPWZCX-UHFFFAOYSA-N 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- JODCAPZFKMTZIO-UHFFFAOYSA-N 2-[2-butoxy-3-chloro-5-[[formyl(hydroxy)amino]methyl]phenoxy]-n-methylacetamide Chemical compound CCCCOC1=C(Cl)C=C(CN(O)C=O)C=C1OCC(=O)NC JODCAPZFKMTZIO-UHFFFAOYSA-N 0.000 claims 1
- HZBJZTSIXIZDEN-UHFFFAOYSA-N 2-[2-butoxy-5-[[formyl(hydroxy)amino]methyl]-3-iodophenoxy]-n-methylacetamide Chemical compound CCCCOC1=C(I)C=C(CN(O)C=O)C=C1OCC(=O)NC HZBJZTSIXIZDEN-UHFFFAOYSA-N 0.000 claims 1
- -1 2-acetylaminoethyl Chemical group 0.000 claims 1
- ZCPSMHHSOQNGPO-UHFFFAOYSA-N 2-butoxy-3-chloro-n-(2,3-dihydroxypropyl)-5-[[formyl(hydroxy)amino]methyl]benzamide Chemical compound CCCCOC1=C(Cl)C=C(CN(O)C=O)C=C1C(=O)NCC(O)CO ZCPSMHHSOQNGPO-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010057190 Respiratory tract infections Diseases 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000002843 carboxylic acid group Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 150000004820 halides Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 150000003951 lactams Chemical group 0.000 claims 1
- LFLKCEXHVDSOSP-UHFFFAOYSA-N methyl 2-butoxy-3-chloro-5-[[formyl(hydroxy)amino]methyl]benzoate Chemical compound CCCCOC1=C(Cl)C=C(CN(O)C=O)C=C1C(=O)OC LFLKCEXHVDSOSP-UHFFFAOYSA-N 0.000 claims 1
- BDGPRJKXISVNCV-UHFFFAOYSA-N n-[(3,5-dichloro-4-cyclohexyloxyphenyl)methyl]-n-hydroxyformamide Chemical compound ClC1=CC(CN(O)C=O)=CC(Cl)=C1OC1CCCCC1 BDGPRJKXISVNCV-UHFFFAOYSA-N 0.000 claims 1
- YGWANUNUOGHLBT-UHFFFAOYSA-N n-[(3,5-dichloro-4-hexan-3-yloxyphenyl)methyl]-n-hydroxyformamide Chemical compound CCCC(CC)OC1=C(Cl)C=C(CN(O)C=O)C=C1Cl YGWANUNUOGHLBT-UHFFFAOYSA-N 0.000 claims 1
- SPLYPHFUBGHHGU-UHFFFAOYSA-N n-[(4-butoxy-2,3-dichloro-5-methoxyphenyl)methyl]-n-hydroxyformamide Chemical compound CCCCOC1=C(Cl)C(Cl)=C(CN(O)C=O)C=C1OC SPLYPHFUBGHHGU-UHFFFAOYSA-N 0.000 claims 1
- JHZKUFWBFOZPSV-UHFFFAOYSA-N n-[(4-butoxy-3,5-dichlorophenyl)methyl]-n-hydroxyformamide Chemical compound CCCCOC1=C(Cl)C=C(CN(O)C=O)C=C1Cl JHZKUFWBFOZPSV-UHFFFAOYSA-N 0.000 claims 1
- OUVXLJYIKQLMED-UHFFFAOYSA-N n-[(4-butoxy-3-chloro-5-hydroxyphenyl)methyl]-n-hydroxyformamide Chemical compound CCCCOC1=C(O)C=C(CN(O)C=O)C=C1Cl OUVXLJYIKQLMED-UHFFFAOYSA-N 0.000 claims 1
- HEHHWHGTAKMZMG-UHFFFAOYSA-N n-[(4-butoxy-3-chloro-5-methoxyphenyl)methyl]-n-hydroxyformamide Chemical compound CCCCOC1=C(Cl)C=C(CN(O)C=O)C=C1OC HEHHWHGTAKMZMG-UHFFFAOYSA-N 0.000 claims 1
- VEKZQCLHSNRFPW-UHFFFAOYSA-N n-[(4-butoxy-3-iodo-5-methoxyphenyl)methyl]-n-hydroxyformamide Chemical compound CCCCOC1=C(I)C=C(CN(O)C=O)C=C1OC VEKZQCLHSNRFPW-UHFFFAOYSA-N 0.000 claims 1
- LRZFRIOXSNNOIE-UHFFFAOYSA-N n-[2-butoxy-5-[[formyl(hydroxy)amino]methyl]-3-iodophenyl]acetamide Chemical compound CCCCOC1=C(I)C=C(CN(O)C=O)C=C1NC(C)=O LRZFRIOXSNNOIE-UHFFFAOYSA-N 0.000 claims 1
- LWXDTDHMFUSZPX-UHFFFAOYSA-N n-[[3,5-dichloro-4-(4-methoxyphenoxy)phenyl]methyl]-n-hydroxyformamide Chemical compound C1=CC(OC)=CC=C1OC1=C(Cl)C=C(CN(O)C=O)C=C1Cl LWXDTDHMFUSZPX-UHFFFAOYSA-N 0.000 claims 1
- OKIFBKIWUPECGB-UHFFFAOYSA-N n-[[3,5-dichloro-4-(pyridin-4-ylmethoxy)phenyl]methyl]-n-hydroxyformamide Chemical compound ClC1=CC(CN(O)C=O)=CC(Cl)=C1OCC1=CC=NC=C1 OKIFBKIWUPECGB-UHFFFAOYSA-N 0.000 claims 1
- YBGSAGVXKGFXQU-JTQLQIEISA-N n-[[3,5-dichloro-4-[(3s)-1-methyl-2,5-dioxopyrrolidin-3-yl]oxyphenyl]methyl]-n-hydroxyformamide Chemical compound O=C1N(C)C(=O)C[C@@H]1OC1=C(Cl)C=C(CN(O)C=O)C=C1Cl YBGSAGVXKGFXQU-JTQLQIEISA-N 0.000 claims 1
- NQCWKPFCFHLBQA-UHFFFAOYSA-N n-[[3,5-dichloro-4-[2-(2-oxopyrrolidin-1-yl)ethoxy]phenyl]methyl]-n-hydroxyformamide Chemical compound ClC1=CC(CN(O)C=O)=CC(Cl)=C1OCCN1C(=O)CCC1 NQCWKPFCFHLBQA-UHFFFAOYSA-N 0.000 claims 1
- DQJXTRDDAANMBO-UHFFFAOYSA-N n-[[3-chloro-4-(3,4-dichlorophenoxy)-5-methoxyphenyl]methyl]-n-hydroxyformamide Chemical compound COC1=CC(CN(O)C=O)=CC(Cl)=C1OC1=CC=C(Cl)C(Cl)=C1 DQJXTRDDAANMBO-UHFFFAOYSA-N 0.000 claims 1
- FFEAKDRRFGXCNV-UHFFFAOYSA-N n-[[4-butoxy-3-iodo-5-(methylamino)phenyl]methyl]-n-hydroxyformamide Chemical compound CCCCOC1=C(I)C=C(CN(O)C=O)C=C1NC FFEAKDRRFGXCNV-UHFFFAOYSA-N 0.000 claims 1
- IHPQTSHIGXTDSC-UHFFFAOYSA-N n-hydroxy-n-[(3-iodo-5-methoxy-4-phenoxyphenyl)methyl]formamide Chemical compound COC1=CC(CN(O)C=O)=CC(I)=C1OC1=CC=CC=C1 IHPQTSHIGXTDSC-UHFFFAOYSA-N 0.000 claims 1
- VDDFKKSLJDMBRA-UHFFFAOYSA-N n-hydroxy-n-[[3-iodo-5-methoxy-4-(2-methoxyethoxy)phenyl]methyl]formamide Chemical compound COCCOC1=C(I)C=C(CN(O)C=O)C=C1OC VDDFKKSLJDMBRA-UHFFFAOYSA-N 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000001113 thiadiazolyl 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
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28161101P | 2001-04-05 | 2001-04-05 | |
| PCT/US2002/010648 WO2003002522A1 (en) | 2001-04-05 | 2002-04-04 | Peptide deformylase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004531580A JP2004531580A (ja) | 2004-10-14 |
| JP2004531580A5 true JP2004531580A5 (enExample) | 2005-12-22 |
| JP4220377B2 JP4220377B2 (ja) | 2009-02-04 |
Family
ID=23078034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003508705A Expired - Fee Related JP4220377B2 (ja) | 2001-04-05 | 2002-04-04 | ペプチドデホルミラーゼ阻害物質 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6967220B2 (enExample) |
| EP (1) | EP1383736B1 (enExample) |
| JP (1) | JP4220377B2 (enExample) |
| AT (1) | ATE433953T1 (enExample) |
| DE (1) | DE60232650D1 (enExample) |
| ES (1) | ES2328563T3 (enExample) |
| WO (1) | WO2003002522A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1664000A1 (en) * | 2003-09-12 | 2006-06-07 | Arpida A/S | Isoxazoles as peptide deformylase inhibitors |
| WO2007040289A1 (en) * | 2005-10-05 | 2007-04-12 | Promeditech Inc. | Deformylase inhibitor, process for the preparation thereof, and composition comprising the same |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS563344B2 (enExample) * | 1971-12-29 | 1981-01-24 | ||
| GB8531838D0 (en) * | 1985-12-30 | 1986-02-05 | Wellcome Found | Aryl derivatives |
| NZ505675A (en) * | 1998-02-07 | 2002-11-26 | British Biotech Pharm | N-alkylamide substituted hydroxamic acid derivatives are used as antibacterial agents |
| AR028075A1 (es) * | 2000-05-05 | 2003-04-23 | Smithkline Beecham Corp | Inhibidores de la peptido-desformilasa |
| AR029916A1 (es) * | 2000-05-05 | 2003-07-23 | Smithkline Beecham Corp | N-formil-n-hidroxi-ariloxi alquilaminas y metodos para tratar infecciones bacterianas |
-
2002
- 2002-04-04 DE DE60232650T patent/DE60232650D1/de not_active Expired - Lifetime
- 2002-04-04 WO PCT/US2002/010648 patent/WO2003002522A1/en not_active Ceased
- 2002-04-04 JP JP2003508705A patent/JP4220377B2/ja not_active Expired - Fee Related
- 2002-04-04 AT AT02770378T patent/ATE433953T1/de not_active IP Right Cessation
- 2002-04-04 EP EP02770378A patent/EP1383736B1/en not_active Expired - Lifetime
- 2002-04-04 US US10/473,060 patent/US6967220B2/en not_active Expired - Fee Related
- 2002-04-04 ES ES02770378T patent/ES2328563T3/es not_active Expired - Lifetime
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