NO125272B - - Google Patents
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- Publication number
- NO125272B NO125272B NO4515/68A NO451568A NO125272B NO 125272 B NO125272 B NO 125272B NO 4515/68 A NO4515/68 A NO 4515/68A NO 451568 A NO451568 A NO 451568A NO 125272 B NO125272 B NO 125272B
- Authority
- NO
- Norway
- Prior art keywords
- biphenylyl
- acid
- solution
- methanol
- hydroxybutyrohydroxamic
- Prior art date
Links
- -1 4-(p-biphenylyl)-3-hydroxybutyrohydroxamic acid Chemical compound 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
- MKOMGFPEFYKIGZ-UHFFFAOYSA-N 3-hydroxy-4-(2-phenylphenyl)butanoic acid Chemical compound OC(=O)CC(O)CC1=CC=CC=C1C1=CC=CC=C1 MKOMGFPEFYKIGZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 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 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 description 3
- 239000002260 anti-inflammatory agent Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 239000001103 potassium chloride Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 206010015150 Erythema Diseases 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 231100000321 erythema Toxicity 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- CCBCHURBDSNSTJ-UHFFFAOYSA-N n-hydroxybutanamide Chemical compound CCCC(=O)NO CCBCHURBDSNSTJ-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB51987/67A GB1171670A (en) | 1967-11-15 | 1967-11-15 | Derivatives of 4-Aryl-3-Hydroxybutyric Acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO125272B true NO125272B (da) | 1972-08-14 |
Family
ID=10462202
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4515/68A NO125272B (da) | 1967-11-15 | 1968-11-14 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3641123A (da) |
| AT (1) | AT283330B (da) |
| BE (1) | BE723917A (da) |
| BR (1) | BR6804068D0 (da) |
| CH (1) | CH507206A (da) |
| DK (1) | DK124536B (da) |
| FR (1) | FR1591547A (da) |
| GB (1) | GB1171670A (da) |
| IE (1) | IE32535B1 (da) |
| NL (1) | NL6816143A (da) |
| NO (1) | NO125272B (da) |
| SE (1) | SE363503B (da) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1382267A (en) * | 1970-05-05 | 1975-01-29 | Rorer Inc William H | Phenylalkanoic acid derivatives |
| US4061668A (en) * | 1974-12-06 | 1977-12-06 | Societa Italo-Britannica L. Manetti - H. Roberts & C. | Process for the preparation of 2-(4-isobutylphenyl)-propiohydroxamic acid |
| US4109013A (en) * | 1974-12-20 | 1978-08-22 | Klinge Pharma Gmbh & Co. | Substituted propanol-(2) derivatives of hydroxamic acids and the use thereof as hypolipemic drugs |
| US4173652A (en) * | 1976-12-18 | 1979-11-06 | Akzona Incorporated | Pharmaceutical hydroxamic acid compositions and uses thereof |
| NL7614113A (nl) * | 1976-12-18 | 1978-06-20 | Akzo Nv | Hydroxamzuren. |
| FR2433505A1 (fr) * | 1978-08-18 | 1980-03-14 | Soissonnais Sucrerie | Procede de fabrication des acides phenoxylactiques, de leurs derives et produits obtenus |
| GB2185479B (en) * | 1986-01-20 | 1990-03-14 | Chinese Acad Med Science | Novel amides, pharmacologically active compositions thereof, processes for the preparation thereof and their medical use |
| US8242282B2 (en) | 2010-05-18 | 2012-08-14 | Taipei Medical University | Histone deacetylase inhibitors |
| CN102267923B (zh) * | 2010-06-04 | 2015-07-15 | 台北医学大学 | 组蛋白去乙酰化酶抑制剂 |
-
1967
- 1967-11-15 GB GB51987/67A patent/GB1171670A/en not_active Expired
-
1968
- 1968-10-31 IE IE1309/68A patent/IE32535B1/xx unknown
- 1968-11-12 AT AT1099568A patent/AT283330B/de not_active IP Right Cessation
- 1968-11-13 NL NL6816143A patent/NL6816143A/xx unknown
- 1968-11-14 FR FR1591547D patent/FR1591547A/fr not_active Expired
- 1968-11-14 NO NO4515/68A patent/NO125272B/no unknown
- 1968-11-14 BE BE723917D patent/BE723917A/xx unknown
- 1968-11-14 BR BR204068/68A patent/BR6804068D0/pt unknown
- 1968-11-15 SE SE15526/68A patent/SE363503B/xx unknown
- 1968-11-15 US US776264A patent/US3641123A/en not_active Expired - Lifetime
- 1968-11-15 DK DK557868AA patent/DK124536B/da unknown
- 1968-11-15 CH CH1708268A patent/CH507206A/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH507206A (de) | 1971-05-15 |
| BR6804068D0 (pt) | 1973-01-11 |
| GB1171670A (en) | 1969-11-26 |
| US3641123A (en) | 1972-02-08 |
| DK124536B (da) | 1972-10-30 |
| BE723917A (da) | 1969-04-16 |
| IE32535B1 (en) | 1973-09-05 |
| NL6816143A (da) | 1969-05-19 |
| AT283330B (de) | 1970-08-10 |
| SE363503B (da) | 1974-01-21 |
| FR1591547A (da) | 1970-04-27 |
| IE32535L (en) | 1969-05-15 |
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