NO135902B - - Google Patents
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- Publication number
- NO135902B NO135902B NO2235/73A NO223573A NO135902B NO 135902 B NO135902 B NO 135902B NO 2235/73 A NO2235/73 A NO 2235/73A NO 223573 A NO223573 A NO 223573A NO 135902 B NO135902 B NO 135902B
- Authority
- NO
- Norway
- Prior art keywords
- ether
- mixture
- added
- hours
- general formula
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 27
- 230000003287 optical effect Effects 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 150000007925 phenylethylamine derivatives Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 89
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 55
- 239000000203 mixture Substances 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
- 238000010992 reflux Methods 0.000 description 15
- 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 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 235000019253 formic acid Nutrition 0.000 description 10
- 239000012259 ether extract Substances 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 7
- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229960001582 fenfluramine Drugs 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- -1 trifluoromethoxyphenyl Chemical group 0.000 description 4
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical class C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 3
- TXDQJVBNHPYFMC-UHFFFAOYSA-N 1-[3-(trifluoromethylsulfanyl)phenyl]propan-2-one Chemical compound CC(=O)CC1=CC=CC(SC(F)(F)F)=C1 TXDQJVBNHPYFMC-UHFFFAOYSA-N 0.000 description 3
- YQKRUFNUEZALSH-UHFFFAOYSA-N 3-(trifluoromethyl)thiobenzaldehyde Chemical compound FC(F)(F)C1=CC=CC(C=S)=C1 YQKRUFNUEZALSH-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000578 anorexic effect Effects 0.000 description 3
- 230000005587 bubbling Effects 0.000 description 3
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- YONLFQNRGZXBBF-KBPBESRZSA-N (2s,3s)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@H](C(=O)O)[C@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-KBPBESRZSA-N 0.000 description 2
- HHOFGCVQXFDPQA-UHFFFAOYSA-N 1-(2-nitroprop-1-enyl)-3-(trifluoromethylsulfanyl)benzene Chemical compound [O-][N+](=O)C(C)=CC1=CC=CC(SC(F)(F)F)=C1 HHOFGCVQXFDPQA-UHFFFAOYSA-N 0.000 description 2
- KNAYQGVZGNYISX-UHFFFAOYSA-N 1-[3-(trifluoromethylsulfanyl)phenyl]propan-2-amine Chemical compound CC(N)CC1=CC=CC(SC(F)(F)F)=C1 KNAYQGVZGNYISX-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- 208000008589 Obesity Diseases 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000004872 arterial blood pressure Effects 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 235000020824 obesity Nutrition 0.000 description 2
- WGSVFWFSJDAYBM-BQYQJAHWSA-N phenyl-2-nitropropene Chemical compound [O-][N+](=O)C(/C)=C/C1=CC=CC=C1 WGSVFWFSJDAYBM-BQYQJAHWSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 230000009291 secondary effect Effects 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- IDVDLPPCDIMEMC-UHFFFAOYSA-N 1-(2-nitroprop-1-enyl)-3-(trifluoromethoxy)benzene Chemical compound [O-][N+](=O)C(C)=CC1=CC=CC(OC(F)(F)F)=C1 IDVDLPPCDIMEMC-UHFFFAOYSA-N 0.000 description 1
- WGSVFWFSJDAYBM-UHFFFAOYSA-N 2-nitroprop-1-enylbenzene Chemical class [O-][N+](=O)C(C)=CC1=CC=CC=C1 WGSVFWFSJDAYBM-UHFFFAOYSA-N 0.000 description 1
- AKVXSWRHCXDNEA-UHFFFAOYSA-N 3-(fluoromethoxy)benzaldehyde Chemical compound FCOC1=CC=CC(C=O)=C1 AKVXSWRHCXDNEA-UHFFFAOYSA-N 0.000 description 1
- FQEVHRCPXFKJHF-UHFFFAOYSA-N 3-(trifluoromethoxy)benzaldehyde Chemical compound FC(F)(F)OC1=CC=CC(C=O)=C1 FQEVHRCPXFKJHF-UHFFFAOYSA-N 0.000 description 1
- DCZAPXGEZYVQNX-UHFFFAOYSA-N 3-(trifluoromethoxy)benzonitrile Chemical compound FC(F)(F)OC1=CC=CC(C#N)=C1 DCZAPXGEZYVQNX-UHFFFAOYSA-N 0.000 description 1
- OQVKGSDRYMYQKF-UHFFFAOYSA-N 3-(trifluoromethyl)benzenecarbothioic s-acid Chemical compound OC(=S)C1=CC=CC(C(F)(F)F)=C1 OQVKGSDRYMYQKF-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000002891 anorexigenic effect Effects 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960001270 d- tartaric acid Drugs 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- RMECOAGRPWRBCA-UHFFFAOYSA-N n-ethyl-1-[3-(trifluoromethoxy)phenyl]propan-2-amine Chemical compound CCNC(C)CC1=CC=CC(OC(F)(F)F)=C1 RMECOAGRPWRBCA-UHFFFAOYSA-N 0.000 description 1
- XJRONEFNAOXUBC-UHFFFAOYSA-N n-methyl-1-[3-(trifluoromethylsulfanyl)phenyl]propan-2-amine Chemical compound CNC(C)CC1=CC=CC(SC(F)(F)F)=C1 XJRONEFNAOXUBC-UHFFFAOYSA-N 0.000 description 1
- JNBRDKSMCQCAGB-UHFFFAOYSA-N n-propyl-1-[3-(trifluoromethylsulfanyl)phenyl]propan-2-amine Chemical compound CCCNC(C)CC1=CC=CC(SC(F)(F)F)=C1 JNBRDKSMCQCAGB-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 210000001147 pulmonary artery Anatomy 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- HNONSDNCRNUTCT-UHFFFAOYSA-N tiflorex Chemical compound CCNC(C)CC1=CC=CC(SC(F)(F)F)=C1 HNONSDNCRNUTCT-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- 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
- C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/32—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to an acyclic carbon atom of the carbon skeleton
-
- 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
-
- 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
- C07C45/44—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reduction and hydrolysis of nitriles
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7219515A FR2186248B1 (sr) | 1972-05-31 | 1972-05-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO135902B true NO135902B (sr) | 1977-03-14 |
| NO135902C NO135902C (sr) | 1977-06-22 |
Family
ID=9099408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2235/73A NO135902C (sr) | 1972-05-31 | 1973-05-29 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3965190A (sr) |
| JP (3) | JPS5037177B2 (sr) |
| AT (1) | AT325018B (sr) |
| AU (2) | AU474952B2 (sr) |
| BE (1) | BE800207A (sr) |
| CA (1) | CA1010904A (sr) |
| CH (1) | CH568267A5 (sr) |
| DE (1) | DE2360318C3 (sr) |
| DK (1) | DK140833B (sr) |
| ES (2) | ES439815A1 (sr) |
| FR (1) | FR2186248B1 (sr) |
| GB (3) | GB1415473A (sr) |
| IE (1) | IE37652B1 (sr) |
| LU (1) | LU67689A1 (sr) |
| NL (1) | NL150436B (sr) |
| NO (1) | NO135902C (sr) |
| SE (1) | SE402456B (sr) |
| ZA (1) | ZA733623B (sr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2272990A1 (en) * | 1974-05-28 | 1975-12-26 | Synthelabo | 1-(Trifluoromethylthio-phenyl)-2-(substd.)amino propane prepn. - in 4 stages from trifluoromethylthio-aniline |
| FR2283673A1 (fr) * | 1974-09-06 | 1976-04-02 | Synthelabo | Nouveaux derives de m-trifluoromethylthio phenethylamine, leurs sels, leur preparation et les medicaments qui en contiennent |
| JPS522486U (sr) * | 1975-06-24 | 1977-01-08 | ||
| US4038415A (en) * | 1975-08-07 | 1977-07-26 | Nelson Research & Development Company | Prostaglandin dehydrogenase inhibiting agents |
| FR2447907A1 (fr) * | 1979-02-05 | 1980-08-29 | Synthelabo | Derives de phenyl-1 amino-2 propane et leur application en therapeutique |
| JPS5947068U (ja) * | 1982-09-21 | 1984-03-28 | タキゲン製造株式会社 | 軸方向ピンタンブラ錠 |
| JPS5972366A (ja) * | 1982-10-19 | 1984-04-24 | 株式会社サンポウロツク | 軸方向ピンタンブラ錠 |
| US4562292A (en) * | 1983-08-18 | 1985-12-31 | The Regents Of The University Of California | Trifluoromethylketone sulfides and reversible enzyme inhibition therewith |
| JPS61141920U (sr) * | 1985-02-20 | 1986-09-02 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1047082A (en) | 1963-02-01 | 1966-11-02 | Pfizer & Co C | Thyronine derivatives |
| US3748361A (en) * | 1971-04-28 | 1973-07-24 | Exxon Research Engineering Co | Halo-substituted oxime carbamates |
| US3763142A (en) * | 1971-11-09 | 1973-10-02 | Sandoz Ag | Thiazolodiazepines |
-
1972
- 1972-05-31 FR FR7219515A patent/FR2186248B1/fr not_active Expired
-
1973
- 1973-05-18 DE DE2360318A patent/DE2360318C3/de not_active Expired
- 1973-05-25 GB GB896475A patent/GB1415473A/en not_active Expired
- 1973-05-25 GB GB893575A patent/GB1415472A/en not_active Expired
- 1973-05-25 GB GB2508073A patent/GB1415471A/en not_active Expired
- 1973-05-28 ZA ZA733623A patent/ZA733623B/xx unknown
- 1973-05-29 BE BE131666A patent/BE800207A/xx not_active IP Right Cessation
- 1973-05-29 NO NO2235/73A patent/NO135902C/no unknown
- 1973-05-29 LU LU67689A patent/LU67689A1/xx unknown
- 1973-05-29 SE SE7307595A patent/SE402456B/xx unknown
- 1973-05-30 AT AT476273A patent/AT325018B/de not_active IP Right Cessation
- 1973-05-30 DK DK300673AA patent/DK140833B/da unknown
- 1973-05-30 CA CA172,728A patent/CA1010904A/en not_active Expired
- 1973-05-30 CH CH787973A patent/CH568267A5/xx not_active IP Right Cessation
- 1973-05-30 US US05/365,181 patent/US3965190A/en not_active Expired - Lifetime
- 1973-05-30 NL NL737307572A patent/NL150436B/xx unknown
- 1973-05-31 IE IE804/73A patent/IE37652B1/xx unknown
- 1973-05-31 JP JP48061409A patent/JPS5037177B2/ja not_active Expired
- 1973-06-04 AU AU56463/73A patent/AU474952B2/en not_active Expired
-
1975
- 1975-05-26 JP JP50062832A patent/JPS5123232A/ja active Pending
- 1975-05-26 JP JP50062833A patent/JPS5123231A/ja active Pending
- 1975-07-29 ES ES439815A patent/ES439815A1/es not_active Expired
- 1975-07-29 ES ES439816A patent/ES439816A1/es not_active Expired
-
1976
- 1976-07-09 AU AU15789/76A patent/AU1578976A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL150436B (nl) | 1976-08-16 |
| AT325018B (de) | 1975-09-25 |
| FR2186248B1 (sr) | 1975-11-28 |
| AU1578976A (en) | 1976-10-14 |
| DE2360318B2 (de) | 1977-10-27 |
| FR2186248A1 (sr) | 1974-01-11 |
| LU67689A1 (sr) | 1973-12-10 |
| BE800207A (fr) | 1973-11-29 |
| NL7307572A (sr) | 1973-12-04 |
| JPS5123231A (sr) | 1976-02-24 |
| IE37652B1 (en) | 1977-09-14 |
| ES439815A1 (es) | 1977-04-16 |
| AU5646373A (en) | 1974-12-05 |
| DE2360317B2 (de) | 1977-07-07 |
| DE2360318A1 (de) | 1974-05-16 |
| AU474952B2 (en) | 1976-08-05 |
| DE2360317A1 (de) | 1974-05-16 |
| US3965190A (en) | 1976-06-22 |
| DE2360318C3 (de) | 1978-06-29 |
| GB1415473A (en) | 1975-11-26 |
| JPS5037177B2 (sr) | 1975-12-01 |
| DK140833C (sr) | 1980-06-02 |
| ES439816A1 (es) | 1977-04-16 |
| ZA733623B (en) | 1974-04-24 |
| JPS4961129A (sr) | 1974-06-13 |
| SE402456B (sv) | 1978-07-03 |
| IE37652L (en) | 1973-11-30 |
| NO135902C (sr) | 1977-06-22 |
| CH568267A5 (sr) | 1975-10-31 |
| JPS5123232A (sr) | 1976-02-24 |
| DK140833B (da) | 1979-11-26 |
| GB1415472A (en) | 1975-11-26 |
| CA1010904A (en) | 1977-05-24 |
| GB1415471A (en) | 1975-11-26 |
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