BE648892A - - Google Patents
Info
- Publication number
- BE648892A BE648892A BE648892A BE648892A BE648892A BE 648892 A BE648892 A BE 648892A BE 648892 A BE648892 A BE 648892A BE 648892 A BE648892 A BE 648892A BE 648892 A BE648892 A BE 648892A
- Authority
- BE
- Belgium
- Prior art keywords
- acid
- acids
- substituted
- condensed
- hydroxylamine
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 47
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 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 claims description 14
- 150000007513 acids Chemical class 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims description 6
- FPOQLQZHRCEVOT-UHFFFAOYSA-N N-hydroxy-2-phenylacetamide Chemical class ONC(=O)CC1=CC=CC=C1 FPOQLQZHRCEVOT-UHFFFAOYSA-N 0.000 claims description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- NUWNUNRECZGDII-UHFFFAOYSA-N n-hydroxy-2-phenoxyacetamide Chemical class ONC(=O)COC1=CC=CC=C1 NUWNUNRECZGDII-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- -1 p-isoamyl phenylacethydroxamic acid p-n-propylphenylacethydroxamic acid Chemical compound 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 229910001868 water Inorganic materials 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229910015400 FeC13 Inorganic materials 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- SOQZMRZFFNHBLK-UHFFFAOYSA-N 2-(4-tert-butylphenoxy)-N-hydroxyacetamide Chemical compound CC(C)(C)C1=CC=C(OCC(=O)NO)C=C1 SOQZMRZFFNHBLK-UHFFFAOYSA-N 0.000 description 2
- QKJPXROEIJPNHG-UHFFFAOYSA-N 2-(4-tert-butylphenyl)acetonitrile Chemical compound CC(C)(C)C1=CC=C(CC#N)C=C1 QKJPXROEIJPNHG-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- 238000007265 chloromethylation reaction Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 230000000871 hypocholesterolemic effect Effects 0.000 description 2
- HXVTYMWVMVKVTF-UHFFFAOYSA-N methyl 2-(4-tert-butylphenyl)acetate Chemical compound COC(=O)CC1=CC=C(C(C)(C)C)C=C1 HXVTYMWVMVKVTF-UHFFFAOYSA-N 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 229940127557 pharmaceutical product Drugs 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 230000002936 tranquilizing effect Effects 0.000 description 2
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 1
- WAXIFMGAKWIFDQ-UHFFFAOYSA-N 1-tert-butyl-4-(chloromethyl)benzene Chemical compound CC(C)(C)C1=CC=C(CCl)C=C1 WAXIFMGAKWIFDQ-UHFFFAOYSA-N 0.000 description 1
- TXCTURVQEPLVTE-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-n-hydroxyacetamide Chemical compound CC(C)(C)C1=CC=C(CC(=O)NO)C=C1 TXCTURVQEPLVTE-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- UTDXUMYKIRMAOH-UHFFFAOYSA-N N-hydroxy-2-(4-propylphenyl)acetamide Chemical compound C(CC)C1=CC=C(C=C1)CC(=O)NO UTDXUMYKIRMAOH-UHFFFAOYSA-N 0.000 description 1
- 241000080683 Seila Species 0.000 description 1
- 206010000269 abscess Diseases 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001741 anti-phlogistic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- XKOOVHYJLVRPNR-UHFFFAOYSA-N ethyl 2-(4-tert-butylphenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C(C(C)(C)C)C=C1 XKOOVHYJLVRPNR-UHFFFAOYSA-N 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- OIWYKTQRGOGUJE-UHFFFAOYSA-N n-hydroxy-2-[4-(2-methylpropoxy)phenyl]acetamide Chemical compound CC(C)COC1=CC=C(CC(=O)NO)C=C1 OIWYKTQRGOGUJE-UHFFFAOYSA-N 0.000 description 1
- KXWBJMRKTBNVNY-UHFFFAOYSA-N n-hydroxy-2-[4-(2-methylpropyl)phenyl]acetamide Chemical compound CC(C)CC1=CC=C(CC(=O)NO)C=C1 KXWBJMRKTBNVNY-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000020095 red wine Nutrition 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE648892A BE648892A (d) | 1964-06-05 | 1964-06-05 | |
| NL6406688A NL6406688A (d) | 1964-06-05 | 1964-06-12 | |
| GB23882/67A GB1110520A (en) | 1964-06-05 | 1965-05-25 | Arylacetic acid amides |
| GB22074/65A GB1102867A (en) | 1964-06-05 | 1965-05-25 | Substituted acethydroxamic acids and processes of preparation thereof |
| BR169972/65A BR6569972D0 (pt) | 1964-06-05 | 1965-05-27 | Processo para preparacao de novos acidos hidroxamicos |
| DE19651618708 DE1618708A1 (de) | 1964-06-05 | 1965-06-01 | Verfahren zur Herstellung von substituierten Phenylacetamiden |
| DE19651768406 DE1768406C (de) | 1964-06-05 | 1965-06-01 | Phenylacetylhydroxamsäuren. Ausscheidung aus: 1280254 |
| DEM65418A DE1280254B (de) | 1964-06-05 | 1965-06-01 | Verfahren zur Herstellung von Phenylacetylhydroxamsaeuren |
| FR19261A FR1484624A (fr) | 1964-06-05 | 1965-06-02 | Procédés de préparation d'acides acéthydroxamiques substitués et d'amides correspondants |
| AT505665A AT262973B (de) | 1964-06-05 | 1965-06-03 | Verfahren zur Herstellung neuer substituierter Phenylacethydroxamsäuren |
| DK280465AA DK117353B (da) | 1964-06-05 | 1965-06-03 | Fremgangsmåde til fremstilling af substituerede arylacethydroxamsyrer. |
| AT778266A AT263756B (de) | 1964-06-05 | 1965-06-03 | Verfahren zur Herstellung neuer substituierter Phenylacetamide |
| SE7271/65A SE345260B (d) | 1964-06-05 | 1965-06-03 | |
| ES0313832A ES313832A1 (es) | 1964-06-05 | 1965-06-04 | Procedimiento para preparar acidos arilacetohidroxamicos sustituidos. |
| CS3630A CS161685B2 (d) | 1964-06-05 | 1965-06-04 | |
| OA52053A OA02009A (fr) | 1964-06-05 | 1965-06-04 | Procédés de préparation d'acide acéthydroxamiques substitués et d'amides correspondants. |
| FI651347A FI51806C (fi) | 1964-06-05 | 1965-06-05 | Menetelmä lääkinnässä ja lääkkeiden valmistuksessa käytettävien substi tuoitujen fenyyliasethydroksaamihappojen valmistamiseksi. |
| NL656507265A NL143132B (nl) | 1964-06-05 | 1965-06-08 | Werkwijze ter bereiding van een geneesmiddel, gevormd geneesmiddel en werkwijze ter bereiding van de daarbij te gebruiken geneeskrachtige verbindingen. |
| US751710A US3479396A (en) | 1964-06-05 | 1968-08-12 | Substituted arylacetohydroxamic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE648892A BE648892A (d) | 1964-06-05 | 1964-06-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE648892A true BE648892A (d) | 1964-10-01 |
Family
ID=3846608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE648892A BE648892A (d) | 1964-06-05 | 1964-06-05 |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE648892A (d) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7879911B2 (en) | 2007-02-01 | 2011-02-01 | Johnson Alan T | Hydroxamic acid derivatives of phenoxy-acetic acids and analogs useful as therapeutic agents for treating anthrax poisoning |
| CN115974688A (zh) * | 2023-02-02 | 2023-04-18 | 滕州市悟通香料有限责任公司 | 一种对叔丁基苯乙酸甲酯的合成方法 |
-
1964
- 1964-06-05 BE BE648892A patent/BE648892A/fr unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7879911B2 (en) | 2007-02-01 | 2011-02-01 | Johnson Alan T | Hydroxamic acid derivatives of phenoxy-acetic acids and analogs useful as therapeutic agents for treating anthrax poisoning |
| CN115974688A (zh) * | 2023-02-02 | 2023-04-18 | 滕州市悟通香料有限责任公司 | 一种对叔丁基苯乙酸甲酯的合成方法 |
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