JP2002515427A - 抗菌剤としてのヒドロキサム酸誘導体 - Google Patents
抗菌剤としてのヒドロキサム酸誘導体Info
- Publication number
- JP2002515427A JP2002515427A JP2000549233A JP2000549233A JP2002515427A JP 2002515427 A JP2002515427 A JP 2002515427A JP 2000549233 A JP2000549233 A JP 2000549233A JP 2000549233 A JP2000549233 A JP 2000549233A JP 2002515427 A JP2002515427 A JP 2002515427A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- hydrogen
- phenyl
- group
- alkenyl
- 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.)
- Withdrawn
Links
- 239000003242 anti bacterial agent Substances 0.000 title claims description 10
- 239000002253 acid Substances 0.000 title claims description 8
- 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 title description 6
- -1 hydroxy, mercapto Chemical class 0.000 claims abstract description 134
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 63
- 239000001257 hydrogen Substances 0.000 claims abstract description 58
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 46
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 42
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 30
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 125000005843 halogen group Chemical group 0.000 claims abstract description 12
- 239000004599 antimicrobial Substances 0.000 claims abstract description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 5
- 125000002346 iodo group Chemical group I* 0.000 claims abstract description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 230000000845 anti-microbial effect Effects 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 3
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 239000004475 Arginine Substances 0.000 claims description 3
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims description 3
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 3
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 3
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims description 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 3
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 3
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 3
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 3
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004472 Lysine Substances 0.000 claims description 3
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 3
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims description 3
- 239000004473 Threonine Substances 0.000 claims description 3
- 235000001014 amino acid Nutrition 0.000 claims description 3
- 229940024606 amino acid Drugs 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 3
- 235000009697 arginine Nutrition 0.000 claims description 3
- 235000009582 asparagine Nutrition 0.000 claims description 3
- 229960001230 asparagine Drugs 0.000 claims description 3
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 235000018417 cysteine Nutrition 0.000 claims description 3
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 235000013922 glutamic acid Nutrition 0.000 claims description 3
- 239000004220 glutamic acid Substances 0.000 claims description 3
- 235000014304 histidine Nutrition 0.000 claims description 3
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 3
- 208000015181 infectious disease Diseases 0.000 claims description 3
- 235000018977 lysine Nutrition 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 235000004400 serine Nutrition 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 235000008521 threonine Nutrition 0.000 claims description 3
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 2
- 208000035143 Bacterial infection Diseases 0.000 claims description 2
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims description 2
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- 235000006109 methionine Nutrition 0.000 claims description 2
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- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004344 phenylpropyl group Chemical group 0.000 claims description 2
- 239000004474 valine Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 2
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical compound COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 claims 1
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- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims 1
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- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 7
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Classifications
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
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- 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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4453—Non condensed piperidines, e.g. piperocaine only substituted in position 1, e.g. propipocaine, diperodon
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- A61K31/16—Amides, e.g. hydroxamic acids
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- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
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- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
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- 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
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- 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
- A61K31/4402—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 2, e.g. pheniramine, bisacodyl
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- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Emergency Medicine (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9810464.9A GB9810464D0 (en) | 1998-05-16 | 1998-05-16 | Hydroxamic acid derivatives |
| GB9810464.9 | 1998-05-16 | ||
| PCT/GB1999/001541 WO1999059568A1 (en) | 1998-05-16 | 1999-05-14 | Hydroxamic acid derivatives as antibacterials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002515427A true JP2002515427A (ja) | 2002-05-28 |
| JP2002515427A5 JP2002515427A5 (enExample) | 2006-07-13 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000549233A Withdrawn JP2002515427A (ja) | 1998-05-16 | 1999-05-14 | 抗菌剤としてのヒドロキサム酸誘導体 |
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| Country | Link |
|---|---|
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| EP (2) | EP1079819B1 (enExample) |
| JP (1) | JP2002515427A (enExample) |
| KR (1) | KR100634089B1 (enExample) |
| CN (1) | CN1300210A (enExample) |
| AT (1) | ATE347356T1 (enExample) |
| AU (1) | AU754063B2 (enExample) |
| BR (1) | BR9910488A (enExample) |
| CA (1) | CA2332713C (enExample) |
| CY (1) | CY1106452T1 (enExample) |
| DE (1) | DE69934309T2 (enExample) |
| DK (1) | DK1079819T3 (enExample) |
| ES (1) | ES2278444T3 (enExample) |
| GB (2) | GB9810464D0 (enExample) |
| HU (1) | HUP0102290A3 (enExample) |
| IL (2) | IL139059A0 (enExample) |
| NO (1) | NO20005782L (enExample) |
| NZ (1) | NZ507560A (enExample) |
| PL (1) | PL344438A1 (enExample) |
| PT (1) | PT1079819E (enExample) |
| TR (1) | TR200003376T2 (enExample) |
| WO (1) | WO1999059568A1 (enExample) |
| ZA (1) | ZA200006131B (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL137312A (en) * | 1998-02-07 | 2005-12-18 | Vernalis Oxford Ltd | Pharmaceutical anti-bacterial compositions comprising n-formyl hydroxylamine derivatives and severalsuch derivatives |
| GB9810464D0 (en) * | 1998-05-16 | 1998-07-15 | British Biotech Pharm | Hydroxamic acid derivatives |
| ATE293600T1 (de) * | 1999-08-10 | 2005-05-15 | Vernalis Oxford Ltd | Antibakterielle mittel |
| WO2001040198A2 (fr) * | 1999-11-30 | 2001-06-07 | Aventis Pharma S.A. | Derives macrocycliques de l'acide hydroxamique et leur utilisation en tant qu'antimicrobiens |
| FR2801591B1 (fr) * | 1999-11-30 | 2002-03-01 | Aventis Pharma Sa | Derives macrocycliques de l'acide hydroxamique, leur preparation et les compositions qui les contiennent |
| JP2003534239A (ja) * | 1999-12-17 | 2003-11-18 | ヴァージコア・インコーポレーテッド | 新規なスクシナート化合物、組成物、並びに使用及び調製方法 |
| GB9929979D0 (en) * | 1999-12-17 | 2000-02-09 | Darwin Discovery Ltd | Hydroxamic acid derivatives |
| WO2002028829A2 (en) * | 2000-09-25 | 2002-04-11 | Questcor Pharmaceuticals, Inc. | Peptide deformylase inhibitors |
| WO2002041886A1 (en) * | 2000-11-23 | 2002-05-30 | British Biotech Pharmaceuticals Ltd | Ydroxamic acid or n-formyl hydroxylamine derivatives as inhibitors of bakterial polypeptide deformylase for treating microbial infections |
| US6660741B2 (en) * | 2001-03-19 | 2003-12-09 | Sloan-Kettering Institute For Cancer Research | Asymmetric synthesis of (S,S,R)-(-)-actinonin and its analogs and uses therefor |
| WO2002081426A1 (en) * | 2001-04-05 | 2002-10-17 | Smithkline Beecham Corporation | Peptide deformylase inhibitors |
| GB0128943D0 (en) | 2001-12-04 | 2002-01-23 | Novo Pharmaceuticals De Ltd | Bacterial enzyme inhibitors |
| JP4190862B2 (ja) * | 2001-12-18 | 2008-12-03 | シャープ株式会社 | 表示装置およびその駆動方法 |
| GB0208579D0 (en) * | 2002-04-13 | 2002-05-22 | British Biotech Pharm | Antibacterial agents |
| DE10320453A1 (de) * | 2003-05-08 | 2004-11-25 | Morphochem AG Aktiengesellschaft für kombinatorische Chemie | Neue Bioisostere von Actinonin |
| ES2582555T3 (es) * | 2007-11-29 | 2016-09-13 | Inolex Investment Corporation | Conservantes para composiciones cosméticas, de tocador y farmacéuticas |
| DE102011088962A1 (de) * | 2011-12-19 | 2013-06-20 | Beiersdorf Ag | Wirkstoffkombinationen aus einer oder mehreren Carbonsäuren, insbesondereHydroxycarbonsäuren, und einer oder mehreren physiologisch unbedenklichen Hydroxamsäure sowie kosmetische oder dermatologische Zubereitungen, solcheWirkstoffkombinationen enthaltend |
| US10829440B2 (en) | 2015-06-12 | 2020-11-10 | Brown University | Antibacterial compounds and methods of making and using same |
| CN111787800B (zh) * | 2017-06-29 | 2022-11-25 | 金伯利-克拉克环球有限公司 | 包含二异羟肟酸的抗微生物组合物及用其抑制微生物生长的方法 |
| CN108672095A (zh) * | 2018-05-04 | 2018-10-19 | 广东省资源综合利用研究所 | γ-羟基烷基羟肟酸及其制备方法与应用 |
| US11555010B2 (en) | 2019-07-25 | 2023-01-17 | Brown University | Diamide antimicrobial agents |
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| GB1028921A (en) * | 1962-01-23 | 1966-05-11 | Ranjeet Bhagwan Singh | New antibiotic |
| US4303662A (en) * | 1980-11-24 | 1981-12-01 | E. R. Squibb & Sons, Inc. | Carboxyacyl, mercapto and acylmercapto derivatives of heterobicyclo compounds |
| JPH0670019B2 (ja) * | 1989-07-21 | 1994-09-07 | 明治製菓株式会社 | 新抗生物質ｓｆ２１９７ｃ物質およびその製造法 |
| GB8919251D0 (en) * | 1989-08-24 | 1989-10-04 | British Bio Technology | Compounds |
| JPH03157372A (ja) * | 1989-11-13 | 1991-07-05 | Yamanouchi Pharmaceut Co Ltd | Ｙｌ―０１８６９ｐ物質及びその製造法 |
| WO1992022523A2 (en) * | 1991-06-14 | 1992-12-23 | Research Corporation Technologies, Inc. | Peptide derivatives of collagenase inhibitor |
| GB9223904D0 (en) | 1992-11-13 | 1993-01-06 | British Bio Technology | Inhibition of cytokine production |
| NZ271893A (en) * | 1993-08-23 | 1997-11-24 | Immunex Corp | Inhibitors of tnf-alpha secretion |
| JP3157372B2 (ja) | 1993-11-29 | 2001-04-16 | 三洋電機株式会社 | フィルタ |
| DK0766664T3 (da) * | 1994-06-22 | 2000-07-31 | British Biotech Pharm | Metalloproteinaseinhibitorer |
| US5532265A (en) * | 1994-11-30 | 1996-07-02 | The Board Of Trustees Of The Leland Stanford Junior University | Treatment of central nervous system inflammatory disease with matrix metalloprotease inhibitors |
| GB9507799D0 (en) * | 1995-04-18 | 1995-05-31 | British Biotech Pharm | Metalloproteinase inhibitors |
| US6281245B1 (en) * | 1996-10-28 | 2001-08-28 | Versicor, Inc. | Methods for solid-phase synthesis of hydroxylamine compounds and derivatives, and combinatorial libraries thereof |
| EP0942746B1 (en) * | 1996-12-06 | 2005-03-16 | Fonden Til Fremme Af Eksperimentel Cancerforskning | Inhibition of invasive remodelling |
| ZA9711121B (en) * | 1996-12-13 | 1998-06-23 | Handelman Joseph H | Reduction of hair growth. |
| IL137312A (en) * | 1998-02-07 | 2005-12-18 | Vernalis Oxford Ltd | Pharmaceutical anti-bacterial compositions comprising n-formyl hydroxylamine derivatives and severalsuch derivatives |
| GB9810464D0 (en) * | 1998-05-16 | 1998-07-15 | British Biotech Pharm | Hydroxamic acid derivatives |
-
1998
- 1998-05-16 GB GBGB9810464.9A patent/GB9810464D0/en not_active Ceased
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1999
- 1999-05-14 CN CN99806057A patent/CN1300210A/zh active Pending
- 1999-05-14 CA CA002332713A patent/CA2332713C/en not_active Expired - Fee Related
- 1999-05-14 AT AT99922317T patent/ATE347356T1/de not_active IP Right Cessation
- 1999-05-14 ES ES99922317T patent/ES2278444T3/es not_active Expired - Lifetime
- 1999-05-14 EP EP99922317A patent/EP1079819B1/en not_active Expired - Lifetime
- 1999-05-14 HU HU0102290A patent/HUP0102290A3/hu unknown
- 1999-05-14 JP JP2000549233A patent/JP2002515427A/ja not_active Withdrawn
- 1999-05-14 PT PT99922317T patent/PT1079819E/pt unknown
- 1999-05-14 US US09/700,424 patent/US6441042B1/en not_active Expired - Fee Related
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- 1999-05-14 IL IL13905999A patent/IL139059A0/xx not_active IP Right Cessation
- 1999-05-14 DE DE69934309T patent/DE69934309T2/de not_active Expired - Fee Related
- 1999-05-14 TR TR2000/03376T patent/TR200003376T2/xx unknown
- 1999-05-14 BR BR9910488-1A patent/BR9910488A/pt not_active Application Discontinuation
- 1999-05-14 GB GB0024789A patent/GB2353708A/en not_active Withdrawn
- 1999-05-14 KR KR1020007012819A patent/KR100634089B1/ko not_active Expired - Fee Related
- 1999-05-14 EP EP06009622A patent/EP1754477A3/en not_active Withdrawn
- 1999-05-14 WO PCT/GB1999/001541 patent/WO1999059568A1/en not_active Ceased
- 1999-05-14 AU AU39421/99A patent/AU754063B2/en not_active Ceased
- 1999-05-14 NZ NZ507560A patent/NZ507560A/xx unknown
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2000
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- 2000-10-30 ZA ZA200006131A patent/ZA200006131B/en unknown
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- 2002-06-26 US US10/179,227 patent/US6992190B2/en not_active Expired - Fee Related
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