JP4220377B2 - 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
- JP4220377B2 JP4220377B2 JP2003508705A JP2003508705A JP4220377B2 JP 4220377 B2 JP4220377 B2 JP 4220377B2 JP 2003508705 A JP2003508705 A JP 2003508705A JP 2003508705 A JP2003508705 A JP 2003508705A JP 4220377 B2 JP4220377 B2 JP 4220377B2
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- formamide
- benzyl
- butoxy
- dichloro
- 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.)
- Expired - Fee Related
Links
- 239000000081 peptide deformylase inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 62
- -1 2-acetylaminoethyl Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 7
- 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 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 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 description 4
- 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 description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 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 description 3
- 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 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 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 description 2
- 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 description 2
- 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 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000003951 lactams Chemical class 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 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 description 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 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 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 125000005556 thienylene group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 20
- 239000003112 inhibitor Substances 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 239000003039 volatile agent Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000002953 preparative HPLC Methods 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000001408 amides Chemical group 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 5
- 241000588724 Escherichia coli Species 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 150000001412 amines Chemical group 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
- 101710181812 Methionine aminopeptidase Proteins 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 108010026809 Peptide deformylase Proteins 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
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- 238000009472 formulation Methods 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- KDGKTJGPFXIBEB-UHFFFAOYSA-N n-hydroxyformamide Chemical compound ONC=O KDGKTJGPFXIBEB-UHFFFAOYSA-N 0.000 description 4
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- 235000019198 oils Nutrition 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 108090000765 processed proteins & peptides Proteins 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 4
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- 102100021418 Peptide deformylase, mitochondrial Human genes 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000001298 alcohols Chemical group 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
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- 125000004122 cyclic group Chemical group 0.000 description 3
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- 230000000694 effects Effects 0.000 description 3
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- SQKUSGDAQJJKBT-UHFFFAOYSA-N 2,6-dichloro-4-(hydroxymethyl)phenol Chemical compound OCC1=CC(Cl)=C(O)C(Cl)=C1 SQKUSGDAQJJKBT-UHFFFAOYSA-N 0.000 description 2
- SZSLTJRSHCOYNP-UHFFFAOYSA-N 3-amino-4-butoxy-5-iodobenzaldehyde Chemical compound CCCCOC1=C(N)C=C(C=O)C=C1I SZSLTJRSHCOYNP-UHFFFAOYSA-N 0.000 description 2
- SWBBWWCRHKXGAH-UHFFFAOYSA-N 4-butoxy-3-chloro-5-methoxybenzaldehyde Chemical compound CCCCOC1=C(Cl)C=C(C=O)C=C1OC SWBBWWCRHKXGAH-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229930182817 methionine Natural products 0.000 description 2
- RAMMTXADNVWMKU-UHFFFAOYSA-N n-[(3,5-dichloro-4-hydroxyphenyl)methyl]-n-phenylmethoxyformamide Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1CN(C=O)OCC1=CC=CC=C1 RAMMTXADNVWMKU-UHFFFAOYSA-N 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/38—2-Pyrrolones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/416—2,5-Pyrrolidine-diones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Detergent Compositions (AREA)
- Enzymes And Modification Thereof (AREA)
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 JP2004531580A5 (enExample) | 2005-12-22 |
| JP4220377B2 true 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
Also Published As
| Publication number | Publication date |
|---|---|
| JP2004531580A (ja) | 2004-10-14 |
| US20040106795A1 (en) | 2004-06-03 |
| ATE433953T1 (de) | 2009-07-15 |
| WO2003002522A8 (en) | 2003-01-30 |
| ES2328563T3 (es) | 2009-11-16 |
| EP1383736A4 (en) | 2006-04-19 |
| WO2003002522A3 (en) | 2003-09-12 |
| EP1383736B1 (en) | 2009-06-17 |
| DE60232650D1 (de) | 2009-07-30 |
| WO2003002522A1 (en) | 2003-01-09 |
| EP1383736A2 (en) | 2004-01-28 |
| US6967220B2 (en) | 2005-11-22 |
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