AU672810B2 - Hydroxamic acid derivatives and their use as anti-inflammatory compounds - Google Patents
Hydroxamic acid derivatives and their use as anti-inflammatory compounds Download PDFInfo
- Publication number
- AU672810B2 AU672810B2 AU47170/93A AU4717093A AU672810B2 AU 672810 B2 AU672810 B2 AU 672810B2 AU 47170/93 A AU47170/93 A AU 47170/93A AU 4717093 A AU4717093 A AU 4717093A AU 672810 B2 AU672810 B2 AU 672810B2
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- Australia
- Prior art keywords
- methylprop
- enyl
- formula
- salt
- compound
- 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.)
- Ceased
Links
- 150000001875 compounds Chemical class 0.000 title claims description 111
- 239000002253 acid Substances 0.000 title claims description 41
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- 230000003110 anti-inflammatory effect Effects 0.000 title description 5
- 150000003839 salts Chemical class 0.000 claims description 57
- 239000012453 solvate Substances 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- -1 {3-[3-(4-cyanophenoxy)phenyl]-1-methylprop-2-enyl}-1-hydroxyurea Chemical compound 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 15
- 238000011321 prophylaxis Methods 0.000 claims description 14
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- RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 claims description 10
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
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- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000001732 thrombotic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Oncology (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Nutrition Science (AREA)
- Communicable Diseases (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929215921A GB9215921D0 (en) | 1992-07-27 | 1992-07-27 | Anti-inflammatory compounds |
| GB9215921 | 1992-07-27 | ||
| PCT/GB1993/001585 WO1994002448A1 (en) | 1992-07-27 | 1993-07-27 | Hydroxamic acid derivatives and their use as anti-inflammatory compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU4717093A AU4717093A (en) | 1994-02-14 |
| AU672810B2 true AU672810B2 (en) | 1996-10-17 |
Family
ID=10719360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU47170/93A Ceased AU672810B2 (en) | 1992-07-27 | 1993-07-27 | Hydroxamic acid derivatives and their use as anti-inflammatory compounds |
Country Status (10)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ283564B6 (cs) * | 1993-11-26 | 1998-05-13 | Pfizer Inc. | 3-Aryl-2-isoxazolin-5-hydroxamové kyseliny a farmaceutické prostředky na jejich bázi |
| MX9603943A (es) * | 1994-03-09 | 1997-04-30 | Pfizer | Compuestos de isoxazolina como inhibidores de 5-lipooxigenasa. |
| CA2210905A1 (en) * | 1995-02-02 | 1996-08-08 | Nikken Chemicals Co., Ltd. | N-hydroxyurea derivatives |
| PT888127E (pt) | 1996-02-13 | 2002-05-31 | Searle & Co | Combinacoes tendo efeitos imunossupresores contendo inibidores de cilcooxigenase-2 e inibidores de 5-lipoxigenase |
| ATE223732T1 (de) | 1996-02-13 | 2002-09-15 | Searle & Co | Arzneimittelkombinationen mit immunosuppressiven wirkungen welche cyclooxygenase-2 inhibitoren und leukotrien lta4 hydrase-inhibitoren enthalten |
| DE69733338T2 (de) | 1996-02-13 | 2006-03-16 | G.D. Searle & Co., Chicago | Zubereitungen, enthaltend einen cyclooxygenase-2-inhibitor und einen leukotrien-b4-rezeptor-antagonisten |
| UA65542C2 (uk) * | 1996-06-25 | 2004-04-15 | Сефалон, Інк. | Спосіб пригнічення надлишкового продукування фактора некрозу пухлин альфа , спосіб полегшення шкідливих ефектів надлишкового продукування фактора некрозу пухлин альфа та спосіб лікування запального стану або захворювання, пов'язаного з фактором некрозу пухлин. |
| SK170599A3 (en) * | 1997-07-31 | 2000-05-16 | Abbott Lab | N-hydroxyformamide derivatives as inhibitors of matrix metalloproteinases |
| US6294573B1 (en) | 1997-08-06 | 2001-09-25 | Abbott Laboratories | Reverse hydroxamate inhibitors of matrix metalloproteinases |
| US6235786B1 (en) | 1997-08-06 | 2001-05-22 | Abbott Laboratories | Reverse hydroxamate inhibitors of matrix metalloproteinases |
| US6288261B1 (en) | 1998-12-18 | 2001-09-11 | Abbott Laboratories | Inhibitors of matrix metalloproteinases |
| WO2000044712A1 (en) * | 1999-01-27 | 2000-08-03 | Abbott Laboratories | N-hydroxyformamide derivatives as inhibitors of matrix metalloproteinases |
| SE0103325D0 (sv) | 2001-10-04 | 2001-10-04 | Astrazeneca Ab | Novel compounds |
| WO2009099174A1 (ja) | 2008-02-07 | 2009-08-13 | Kyorin Pharmaceutical Co., Ltd. | アミノアルコール誘導体を有効成分とする炎症性腸疾患の治療剤又は予防剤 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0196184A2 (en) * | 1985-03-16 | 1986-10-01 | The Wellcome Foundation Limited | Aryl derivatives |
| EP0299761A1 (en) * | 1987-07-15 | 1989-01-18 | The Wellcome Foundation Limited | Anti-inflammatory aryl derivatives |
| WO1992010469A1 (en) * | 1990-12-11 | 1992-06-25 | Pfizer Inc. | Hydroxamic acid derivatives which inhibit lipoxygenase |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU647177B2 (en) * | 1990-07-25 | 1994-03-17 | Abbott Laboratories | Acetylenic urea derivatives having lipoxygenase inhibitory activity |
-
1992
- 1992-07-27 GB GB929215921A patent/GB9215921D0/en active Pending
-
1993
- 1993-07-26 ZA ZA935378A patent/ZA935378B/xx unknown
- 1993-07-26 TW TW082105933A patent/TW246670B/zh active
- 1993-07-26 MX MX9304503A patent/MX9304503A/es unknown
- 1993-07-26 IL IL106472A patent/IL106472A0/xx unknown
- 1993-07-27 CA CA002141214A patent/CA2141214A1/en not_active Abandoned
- 1993-07-27 JP JP6504325A patent/JPH07509462A/ja active Pending
- 1993-07-27 AU AU47170/93A patent/AU672810B2/en not_active Ceased
- 1993-07-27 EP EP93917925A patent/EP0652864A1/en not_active Withdrawn
- 1993-07-27 WO PCT/GB1993/001585 patent/WO1994002448A1/en not_active Application Discontinuation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0196184A2 (en) * | 1985-03-16 | 1986-10-01 | The Wellcome Foundation Limited | Aryl derivatives |
| EP0299761A1 (en) * | 1987-07-15 | 1989-01-18 | The Wellcome Foundation Limited | Anti-inflammatory aryl derivatives |
| WO1992010469A1 (en) * | 1990-12-11 | 1992-06-25 | Pfizer Inc. | Hydroxamic acid derivatives which inhibit lipoxygenase |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0652864A1 (en) | 1995-05-17 |
| GB9215921D0 (en) | 1992-09-09 |
| CA2141214A1 (en) | 1994-02-03 |
| TW246670B (enrdf_load_stackoverflow) | 1995-05-01 |
| IL106472A0 (en) | 1993-11-15 |
| WO1994002448A1 (en) | 1994-02-03 |
| JPH07509462A (ja) | 1995-10-19 |
| AU4717093A (en) | 1994-02-14 |
| MX9304503A (es) | 1994-04-29 |
| ZA935378B (en) | 1995-01-26 |
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