IE46007B1 - Alkali metal salts of 3-substituted 2-phenyl-5-hydroxy-alkanoic acids and new psychostimulant drugs containing said salts - Google Patents
Alkali metal salts of 3-substituted 2-phenyl-5-hydroxy-alkanoic acids and new psychostimulant drugs containing said saltsInfo
- Publication number
- IE46007B1 IE46007B1 IE2476/77A IE247677A IE46007B1 IE 46007 B1 IE46007 B1 IE 46007B1 IE 2476/77 A IE2476/77 A IE 2476/77A IE 247677 A IE247677 A IE 247677A IE 46007 B1 IE46007 B1 IE 46007B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound according
- alkali metal
- oxo
- acid
- hydroxy
- Prior art date
Links
- 229910052783 alkali metal Inorganic materials 0.000 title claims description 16
- -1 Alkali metal salts Chemical class 0.000 title claims description 13
- 239000002253 acid Substances 0.000 title claims description 5
- 150000003839 salts Chemical class 0.000 title description 5
- 150000007513 acids Chemical class 0.000 title 1
- 229940127250 psychostimulant medication Drugs 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 12
- 230000008569 process Effects 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- QFEORWQMMZNZDB-UHFFFAOYSA-N 5-hydroxy-2,3-diphenylhexanoic acid Chemical compound C=1C=CC=CC=1C(CC(O)C)C(C(O)=O)C1=CC=CC=C1 QFEORWQMMZNZDB-UHFFFAOYSA-N 0.000 claims description 10
- TYZJSDDKJONZHL-UHFFFAOYSA-N 5-oxo-2,3-diphenylhexanoic acid Chemical compound C=1C=CC=CC=1C(CC(=O)C)C(C(O)=O)C1=CC=CC=C1 TYZJSDDKJONZHL-UHFFFAOYSA-N 0.000 claims description 8
- 239000003368 psychostimulant agent Substances 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- 206010062519 Poor quality sleep Diseases 0.000 claims description 5
- 125000004494 ethyl ester group Chemical group 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 4
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000001965 increasing effect Effects 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
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- 230000008020 evaporation Effects 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 230000001131 transforming effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- LNRZCHCAPUVAOP-UHFFFAOYSA-N 2,2-diphenylhexanoic acid Chemical compound C=1C=CC=CC=1C(C(O)=O)(CCCC)C1=CC=CC=C1 LNRZCHCAPUVAOP-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 claims 1
- 101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
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- 238000004458 analytical method Methods 0.000 description 6
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- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 2
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- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
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- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 2
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- YTVDJIQHJKUWMU-UHFFFAOYSA-N 5-oxo-2,3-diphenylhexanenitrile Chemical compound C=1C=CC=CC=1C(CC(=O)C)C(C#N)C1=CC=CC=C1 YTVDJIQHJKUWMU-UHFFFAOYSA-N 0.000 description 1
- OKRVHEHNCFHKNU-UHFFFAOYSA-N 6-methyl-3,4-diphenyloxan-2-one Chemical compound O=C1OC(C)CC(C=2C=CC=CC=2)C1C1=CC=CC=C1 OKRVHEHNCFHKNU-UHFFFAOYSA-N 0.000 description 1
- 206010000117 Abnormal behaviour Diseases 0.000 description 1
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- 101100114358 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cog-6 gene Proteins 0.000 description 1
- RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 1
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- 206010039424 Salivary hypersecretion Diseases 0.000 description 1
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
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- 231100000403 acute toxicity Toxicity 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
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- 229960004046 apomorphine Drugs 0.000 description 1
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- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
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- 239000012267 brine Substances 0.000 description 1
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- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
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- 235000011152 sodium sulphate Nutrition 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/38—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/48—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Psychiatry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7636942A FR2373281A2 (fr) | 1976-12-08 | 1976-12-08 | Nouveaux medicaments psychostimulants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE46007L IE46007L (en) | 1978-06-08 |
| IE46007B1 true IE46007B1 (en) | 1983-01-26 |
Family
ID=9180803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2476/77A IE46007B1 (en) | 1976-12-08 | 1977-12-06 | Alkali metal salts of 3-substituted 2-phenyl-5-hydroxy-alkanoic acids and new psychostimulant drugs containing said salts |
Country Status (11)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MA18559A1 (fr) * | 1978-09-05 | 1980-04-01 | Hoechst Lab | Nouveaux derives d'acides carboxyliques 6-alcools, halogenes, leurs procedes de preparation et medicaments les contenant |
-
1976
- 1976-12-08 FR FR7636942A patent/FR2373281A2/fr active Granted
-
1977
- 1977-12-05 BE BE1008561A patent/BE861477R/xx active
- 1977-12-05 DE DE19772754049 patent/DE2754049A1/de not_active Withdrawn
- 1977-12-06 GB GB50753/77A patent/GB1580709A/en not_active Expired
- 1977-12-06 IE IE2476/77A patent/IE46007B1/en unknown
- 1977-12-07 ES ES465193A patent/ES465193A1/es not_active Expired
- 1977-12-07 CA CA000292553A patent/CA1136645A/fr not_active Expired
- 1977-12-07 ZA ZA00777298A patent/ZA777298B/xx unknown
- 1977-12-08 AU AU31379/77A patent/AU509849B2/en not_active Expired
- 1977-12-08 JP JP14802277A patent/JPS5373538A/ja active Granted
- 1977-12-09 IT IT30538/77A patent/IT1092268B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| ZA777298B (en) | 1978-10-25 |
| CA1136645A (fr) | 1982-11-30 |
| JPS5373538A (en) | 1978-06-30 |
| BE861477R (fr) | 1978-06-05 |
| IT1092268B (it) | 1985-07-06 |
| JPS6129939B2 (enrdf_load_html_response) | 1986-07-10 |
| IE46007L (en) | 1978-06-08 |
| GB1580709A (en) | 1980-12-03 |
| DE2754049A1 (de) | 1978-06-15 |
| FR2373281A2 (fr) | 1978-07-07 |
| ES465193A1 (es) | 1978-10-01 |
| FR2373281B2 (enrdf_load_html_response) | 1979-03-30 |
| AU3137977A (en) | 1979-06-14 |
| AU509849B2 (en) | 1980-05-29 |
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