GB1041989A - A process of preparing 1-(2-dimethylaminoethyl)-1-phenylindene and 1-[2-(methylamino) ethyl]-1-phenylindene - Google Patents
A process of preparing 1-(2-dimethylaminoethyl)-1-phenylindene and 1-[2-(methylamino) ethyl]-1-phenylindeneInfo
- Publication number
- GB1041989A GB1041989A GB28248/65A GB2824865A GB1041989A GB 1041989 A GB1041989 A GB 1041989A GB 28248/65 A GB28248/65 A GB 28248/65A GB 2824865 A GB2824865 A GB 2824865A GB 1041989 A GB1041989 A GB 1041989A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenylindene
- phenyl
- alkyl
- indenes
- decarboxylation
- 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.)
- Expired
Links
- KAQPNQMPHIRKJJ-UHFFFAOYSA-N n,n-dimethyl-2-(1-phenylinden-1-yl)ethanamine Chemical compound C1=CC2=CC=CC=C2C1(CCN(C)C)C1=CC=CC=C1 KAQPNQMPHIRKJJ-UHFFFAOYSA-N 0.000 title 1
- HUGLAQUJRPXQOX-UHFFFAOYSA-N n-methyl-2-(1-phenylinden-1-yl)ethanamine Chemical compound C1=CC2=CC=CC=C2C1(CCNC)C1=CC=CC=C1 HUGLAQUJRPXQOX-UHFFFAOYSA-N 0.000 title 1
- DDDMJDJOLKFWEV-UHFFFAOYSA-N 2-(2-phenyl-1H-inden-1-yl)ethanamine Chemical class C1(=CC=CC=C1)C=1C(C2=CC=CC=C2C=1)CCN DDDMJDJOLKFWEV-UHFFFAOYSA-N 0.000 abstract 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 238000006114 decarboxylation reaction Methods 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 150000007522 mineralic acids Chemical class 0.000 abstract 2
- 150000007524 organic acids Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- -1 2-dimethylaminoethyl halide Chemical class 0.000 abstract 1
- ILASZRLOZFHWOJ-UHFFFAOYSA-N 3-phenyl-1h-indene Chemical compound C12=CC=CC=C2CC=C1C1=CC=CC=C1 ILASZRLOZFHWOJ-UHFFFAOYSA-N 0.000 abstract 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 abstract 1
- 239000001828 Gelatine Substances 0.000 abstract 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 abstract 1
- 229910013698 LiNH2 Inorganic materials 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- QTADGTYUHGACBH-UHFFFAOYSA-N N,N-dimethyl-1-(1-phenyl-1H-inden-2-yl)ethanamine Chemical compound CN(C(C)C=1C(C2=CC=CC=C2C1)C1=CC=CC=C1)C QTADGTYUHGACBH-UHFFFAOYSA-N 0.000 abstract 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 abstract 1
- 229910018954 NaNH2 Inorganic materials 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001339 alkali metal compounds Chemical class 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229920000159 gelatin Polymers 0.000 abstract 1
- 235000019322 gelatine Nutrition 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 239000008101 lactose Substances 0.000 abstract 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16B—DEVICES FOR FASTENING OR SECURING CONSTRUCTIONAL ELEMENTS OR MACHINE PARTS TOGETHER, e.g. NAILS, BOLTS, CIRCLIPS, CLAMPS, CLIPS OR WEDGES; JOINTS OR JOINTING
- F16B12/00—Jointing of furniture or the like, e.g. hidden from exterior
- F16B12/44—Leg joints; Corner joints
- F16B12/48—Non-metal leg connections
Landscapes
- Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Mechanical Engineering (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Phenyl-aminoethyl-indenes of the formula <FORM:1041989/C2/1> wherein R is H or CH3 are made by converting 3-phenylindene into its alkali-metal compound by reaction with a strong alkali, e.g. NaNH2, NaH, LiNH2, butyl lithium or sodium triphenylmethyl and reacting either with a 2-dimethylaminoethyl halide or other reactive ester of 2-dimethylaminoethanol, or with an alkyl N-haloethyl-N-methyl carbamate and subjecting the resulting alkyl-N-(b -1-phenyl-indene-(1)-ylethyl)-N-methyl carbamate I to hydrolysis and decarboxylation. Alternatively I is obtained by reacting 1-dimethylaminoethyl-1-phenylindene with an alkyl haloformate and is subjected to hydrolysis and decarboxylation to give a product wherein R = H. The products may be converted into their salts with organic and inorganic acids.ALSO:Pharmaceutical preparations having antidepressant action comprise phenyl-aminoethyl -indenes of the formula <FORM:1041989/A5-A6/1> wherein R = H or CH3, or their pharmaceutically acceptable addition salts with inorganic or organic acids, in a form suitable for oral or parenteral administration e.g. as a sterile aqueous solution for injection or as a blend with lactose and magnesium stearale, encapsulated in gelatine.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39767364A | 1964-09-15 | 1964-09-15 | |
| US457837A US3360435A (en) | 1964-09-15 | 1965-05-21 | Treatment of depressed states |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1041989A true GB1041989A (en) | 1966-09-07 |
Family
ID=27015954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28248/65A Expired GB1041989A (en) | 1964-09-15 | 1965-07-02 | A process of preparing 1-(2-dimethylaminoethyl)-1-phenylindene and 1-[2-(methylamino) ethyl]-1-phenylindene |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3360435A (en) |
| BE (1) | BE667739A (en) |
| BR (1) | BR6571638D0 (en) |
| CH (2) | CH463486A (en) |
| DE (1) | DE1543216B1 (en) |
| ES (1) | ES315465A1 (en) |
| FR (2) | FR1482826A (en) |
| GB (1) | GB1041989A (en) |
| IL (1) | IL23869A (en) |
| NL (1) | NL6509895A (en) |
| SE (2) | SE322770B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE371190B (en) * | 1972-03-24 | 1974-11-11 | Kabi Ab |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2798888A (en) * | 1952-08-12 | 1957-07-09 | Ciba Pharm Prod Inc | Indene and indane compounds and their production |
| NL282517A (en) * | 1961-08-31 |
-
1965
- 1965-05-21 US US457837A patent/US3360435A/en not_active Expired - Lifetime
- 1965-07-02 IL IL23869A patent/IL23869A/en unknown
- 1965-07-02 GB GB28248/65A patent/GB1041989A/en not_active Expired
- 1965-07-17 ES ES0315465A patent/ES315465A1/en not_active Expired
- 1965-07-26 SE SE9813/65A patent/SE322770B/xx unknown
- 1965-07-27 DE DE19651543216 patent/DE1543216B1/en active Pending
- 1965-07-28 BR BR171638/65A patent/BR6571638D0/en unknown
- 1965-07-29 CH CH1068665A patent/CH463486A/en unknown
- 1965-07-29 CH CH1114968A patent/CH473760A/en not_active IP Right Cessation
- 1965-07-30 FR FR26746A patent/FR1482826A/en not_active Expired
- 1965-07-30 NL NL6509895A patent/NL6509895A/xx unknown
- 1965-07-30 BE BE667739D patent/BE667739A/xx unknown
- 1965-07-30 FR FR26747A patent/FR4646M/fr not_active Expired
-
1968
- 1968-06-28 SE SE08871/68A patent/SE332171B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH463486A (en) | 1968-10-15 |
| US3360435A (en) | 1967-12-26 |
| ES315465A1 (en) | 1966-06-01 |
| SE332171B (en) | 1971-02-01 |
| BE667739A (en) | 1966-01-31 |
| FR1482826A (en) | 1967-06-02 |
| IL23869A (en) | 1970-09-17 |
| DE1543216B1 (en) | 1972-11-09 |
| BR6571638D0 (en) | 1973-08-14 |
| NL6509895A (en) | 1966-03-16 |
| CH473760A (en) | 1969-06-15 |
| SE322770B (en) | 1970-04-20 |
| FR4646M (en) | 1966-12-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1489780A (en) | Process of preparing a stable composition containing a compound of the prostaglandin e group | |
| BG49615A3 (en) | Method for preparing of derivatives of 3- substituted tiomethylcephalosporine or their ethyl, or diphenylethyl esters, or their salts | |
| GB1041989A (en) | A process of preparing 1-(2-dimethylaminoethyl)-1-phenylindene and 1-[2-(methylamino) ethyl]-1-phenylindene | |
| GB1174349A (en) | Novel 2-Anilinomethylimidazoline Derivatives and process for the preparation thereof | |
| GB1100754A (en) | New pyrazole derivatives | |
| GB630712A (en) | Process of preparing intermediates useful in the preparation of penicill amine | |
| SU382613A1 (en) | ||
| IE35323B1 (en) | Tropane-3-ol derivatives and processes for their preparation | |
| GB1114018A (en) | Process for producing 4-hydroxycyclohexanecarboxylic acid and derivatives thereof | |
| US2718519A (en) | Process of preparing 6-methyl-delta6-desoxymorphine | |
| GB922187A (en) | Phenothiazines and their preparation | |
| GB1044615A (en) | Basic thymyl ethers and process for their manufacture | |
| SU440060A1 (en) | Method for preparing 3-aminogomoadamantane hydrochloride | |
| GB1329733A (en) | Derivatives of isonipecotic acid and a process for their prepa- ration | |
| GB782469A (en) | Anti-t.b. factor | |
| Horii et al. | Photochemical reaction of the cyclic enamide, 1-methyl-1, 2, 3, 4, 5, 6, 7, 8-octahydro-2-quinolone | |
| GB942664A (en) | Improved methods of producing dimethyl ª -ketoadipate and dimethyl ª -methyl ª -ketoadipate | |
| GB1376500A (en) | Alkyl-iodo ethers their preparation and pharmaceutical compositions containing them | |
| ES392293A1 (en) | Process for the preparation of {8 3-(4-phenyl)-1-(2h)-3,6-dihydro-pyridyl{9 -propoxy or propylthio-anilides or derivatives thereof | |
| GB1057447A (en) | Quinolyl-aminoethanols and process for the preparation thereof | |
| GB1063183A (en) | Iodonium salts and conversion products thereof | |
| GB1397807A (en) | Process for preparing alpha-keto esters | |
| SU1610818A1 (en) | 3-(3-hydroxyaminopropyl)-4-hydroxybutyrate sodium showing antinecrotic and cardiotropic activity | |
| GB190428997A (en) | Process of Treating Creosote and Product of the same. | |
| GB851658A (en) | Production of methylheptenone |