GB916789A - Therapeutic resin complexes - Google Patents
Therapeutic resin complexesInfo
- Publication number
- GB916789A GB916789A GB10299/59A GB1029959A GB916789A GB 916789 A GB916789 A GB 916789A GB 10299/59 A GB10299/59 A GB 10299/59A GB 1029959 A GB1029959 A GB 1029959A GB 916789 A GB916789 A GB 916789A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- prepared
- nitropropane
- methyl
- hydroxy
- 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
- 239000011347 resin Substances 0.000 title abstract 7
- 229920005989 resin Polymers 0.000 title abstract 7
- 230000001225 therapeutic effect Effects 0.000 title abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract 5
- 239000003729 cation exchange resin Substances 0.000 abstract 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 5
- HZYOZOFLFAXDFR-UHFFFAOYSA-N 2-methyl-2-nitro-1-phenylpropan-1-ol Chemical compound [O-][N+](=O)C(C)(C)C(O)C1=CC=CC=C1 HZYOZOFLFAXDFR-UHFFFAOYSA-N 0.000 abstract 4
- 229920002125 Sokalan® Polymers 0.000 abstract 4
- 150000001412 amines Chemical class 0.000 abstract 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 4
- -1 3,4-methylenedioxy group Chemical group 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- ABRWESLGGMHKEA-UHFFFAOYSA-N n-tert-butylaniline Chemical compound CC(C)(C)NC1=CC=CC=C1 ABRWESLGGMHKEA-UHFFFAOYSA-N 0.000 abstract 3
- QYCHNFIOUYTIEC-UHFFFAOYSA-N (1-chloro-2-methyl-2-nitropropyl)benzene Chemical compound [O-][N+](=O)C(C)(C)C(Cl)C1=CC=CC=C1 QYCHNFIOUYTIEC-UHFFFAOYSA-N 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- QFTWUVJQXPFWNM-UHFFFAOYSA-N 2-amino-2-methyl-1-phenylpropan-1-ol Chemical compound CC(C)(N)C(O)C1=CC=CC=C1 QFTWUVJQXPFWNM-UHFFFAOYSA-N 0.000 abstract 2
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 abstract 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract 2
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 2
- 150000001450 anions Chemical class 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000001555 benzenes Chemical class 0.000 abstract 2
- 229910052736 halogen Chemical group 0.000 abstract 2
- 150000002367 halogens Chemical group 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- MTEWAFVECQBILW-UHFFFAOYSA-N n-tert-butylcyclohexanamine Chemical compound CC(C)(C)NC1CCCCC1 MTEWAFVECQBILW-UHFFFAOYSA-N 0.000 abstract 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- OJTKLJUNTHGXRY-UHFFFAOYSA-N (2-methyl-2-nitropropyl)benzene Chemical compound [O-][N+](=O)C(C)(C)CC1=CC=CC=C1 OJTKLJUNTHGXRY-UHFFFAOYSA-N 0.000 abstract 1
- LKMXYTFESDLNMI-UHFFFAOYSA-N 1-(3-aminophenyl)-2-methyl-2-nitropropan-1-ol Chemical class [O-][N+](=O)C(C)(C)C(O)C1=CC=CC(N)=C1 LKMXYTFESDLNMI-UHFFFAOYSA-N 0.000 abstract 1
- FHHDYPZTOJAZGX-UHFFFAOYSA-N 1-chloro-2-methyl-1-phenylpropan-2-amine Chemical compound CC(C)(N)C(Cl)C1=CC=CC=C1 FHHDYPZTOJAZGX-UHFFFAOYSA-N 0.000 abstract 1
- DVCNIIFQWVIZDA-UHFFFAOYSA-N 2,2-bis(methylamino)-1-phenylethanol Chemical compound C1(=CC=CC=C1)C(C(NC)NC)O DVCNIIFQWVIZDA-UHFFFAOYSA-N 0.000 abstract 1
- FHWZAIWJHOEIFH-UHFFFAOYSA-N 2-chloro-1-N,1-N'-dimethyl-2-phenylethane-1,1-diamine Chemical compound C1(=CC=CC=C1)C(C(NC)NC)Cl FHWZAIWJHOEIFH-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 241000790917 Dioxys <bee> Species 0.000 abstract 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- 229910000019 calcium carbonate Inorganic materials 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- FAQBDCPZTMJQOP-UHFFFAOYSA-N n-tert-butylcyclopentanamine Chemical compound CC(C)(C)NC1CCCC1 FAQBDCPZTMJQOP-UHFFFAOYSA-N 0.000 abstract 1
- 150000002828 nitro derivatives Chemical class 0.000 abstract 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002245 particle Substances 0.000 abstract 1
- 239000006187 pill Substances 0.000 abstract 1
- 229910003446 platinum oxide Inorganic materials 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/58—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
- A61K47/585—Ion exchange resins, e.g. polystyrene sulfonic acid resin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/01—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to acyclic carbon atoms
- C07C205/03—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C205/04—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/08—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to acyclic carbon atoms
- C07C205/09—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/14—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to acyclic carbon atoms
- C07C205/16—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to acyclic carbon atoms of a carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/44—Preparation of metal salts or ammonium salts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises a complex of phenyl-t-butylamine or cyclohexyl-t-butylamine with a cross-linked sulphonic acid cation exchange resin and a process for preparing a resin complex of the general formula: <FORM:0916789/IV(a)/1> in which R1 and R11 represent hydrogen, Y a benzene nucleus or a cyclopentyl or cyclohexyl ring, R represents hydrogen or halogen, a hydroxyl, C1-6 alkoxy, C1-6 alkyl, amino, or 3,4-methylenedioxy group, X and X1, which are the same or different, represent C1-6 alkyl, aryl, aralkyl or alkaryl groups, and A represents the anion of a sulphonic acid cation exchange resin, which comprises reducing the corresponding nitro compound to the amine in the presence of a sulphonic acid cation exchange resin or, when the amine is phenyl-t-butylamine, reacting 1-phenyl-1-hydroxy-2-methyl-2-nitropropane with thionyl chloride and catalytically reducing the 1-phenyl-1-chloro-2-methyl-2-nitropropane in the presence of a sulphonic acid cation exchange resin. The complex may also be prepared by adsorbing the amine directly on the resin. Suitable resins are Duolite C-20, IR-120, and XE-69. ("Duolite" is a Registered Trade Mark). Specifications 577,707, 824,337 and U.S.A. Specifications 2,204,539, 2,238,159 and 2,729,607 are referred to.ALSO:Phenyl-t-butylamine is prepared either by reducing 1 - phenyl - 1 - hydroxy - 2 - methyl-2-aminopropane with red phosphorus and hydriodic acid or by hydrogenating 2-phenyl2-chloro-1,1-dimethylethylamine in the presence of palladinized calcium carbonate. Using Adams platinum oxide, alone, palladium on charcoal or Raney nickel as catalysts cyclohexyl-t-butylamine is prepared. Cyclopentyl-t-butylamine is similarly prepared. 1 - Phenyl - 1 - hydroxy-2-methyl-2-aminopropane is prepared by condensing benzaldehyde with 2-nitropropane to give 1-phenyl-1-hydroxy-2-methyl-2-nitropropane which is reduced with zinc and acetic acid. 1 - Phenyl-1-chloro-2-methyl-2-nitropropane is prepared by reacting 1-phenyl-1-hydroxy-2-methyl-2-nitropropane with thionyl chloride. Similarly are prepared from the appropriate benzaldehyde and nitropropane m-tolyl-, m-chlorophenyl- and m-aminophenyl-1-hydroxy2-methyl-2-nitropropanes which with thionyl chloride give the corresponding -1-chloro compounds. 2-Nitro-2,2-dimethyl-1-phenylethane is prepared either by reduction of 1-phenyl-1-hydroxy-2-methyl-2-nitropropane or by condensing benzyl chloride with 2-nitropropane. Similarly are prepared 2-nitro-2,2-dimethyl-1-m-tolyl-, -m-chlorophenyl- and -m-aminophenylethanes. 1-Phenyl - 1 - chloro-2,2-dimethylaminoethane is prepared from 1-phenyl-1-hydroxy-2,2-dimethylaminoethane and thionyl chloride. Specifications 577,707, 824,337 and U.S.A. Specifications 2,204,539, 2,238,159 and 2,729,607 are referred to.ALSO:Therapeutic compositions having appetite-suppressing properties comprise a pharmaceutical carrier and from 2 to 150 milligrams per dosage unit of an amine, present as a resin complex having the general formula <FORM:0916789/VI/1> in which Y represents a benzene nucleus or a saturated five-membered or six-membered carbon ring; R represents hydrogen, halogen, hydroxyl, amino, C1-6 alkoxyl, C1-6 alkyl or 3,4-methylene dioxy; X and X1 represent the same or different C1-6 alkyl, aralkyl, alkaryl or aryl groups; R1 and R11 are hydrogen atoms or C1-6 alkyl p groups and A represents the anion of a sulphonic acid cation exchange resin. Preferably the cross linkage and particle size of the resin are such that a dosage unit of the composition is therapeutically effective for a period of not less than 8 hrs. upon oral administration. Suitable resins include Duolite C-20 ("Duolite" is a Registered Trade Mark), IR-120 and XE-69. Preferred compositions are tablets, capsules or pills which may contain a single daily dose unit, smaller units for multiple doses or larger units for division into single doses. Specifications 577,707, 824,337 and U.S.A. Specifications 2,204,539, 2,238,159 and 2,729,607 are referred to.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US726010A US2990332A (en) | 1958-04-02 | 1958-04-02 | Pharmaceutical preparations comprising cation exchange resin adsorption compounds and treatment therewith |
| US753093A US3084099A (en) | 1958-08-04 | 1958-08-04 | Therapeutic amine-resin complex composition and method of using same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB916789A true GB916789A (en) | 1963-01-30 |
Family
ID=27111252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB10299/59A Expired GB916789A (en) | 1958-04-02 | 1959-03-25 | Therapeutic resin complexes |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE577279A (en) |
| CH (1) | CH391186A (en) |
| DK (1) | DK104116C (en) |
| FR (1) | FR465M (en) |
| GB (1) | GB916789A (en) |
| NL (2) | NL128079C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2332990A1 (en) * | 1975-11-27 | 1977-06-24 | Nicholas Ind Ltd | PREPARATION OF ETHYLAMINE DERIVATIVES |
| EP0356035A3 (en) * | 1988-08-12 | 1991-04-03 | Astra Aktiebolag | Arylkalkyl-amines and -amides having anticonvulsant and neuroprotective properties |
-
0
- NL NL237722D patent/NL237722A/xx unknown
- NL NL128079D patent/NL128079C/xx active
-
1959
- 1959-03-25 GB GB10299/59A patent/GB916789A/en not_active Expired
- 1959-04-01 BE BE577279A patent/BE577279A/en unknown
- 1959-04-02 DK DK115259AA patent/DK104116C/en active
- 1959-04-02 CH CH7151159A patent/CH391186A/en unknown
-
1960
- 1960-08-30 FR FR837135A patent/FR465M/fr active Active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2332990A1 (en) * | 1975-11-27 | 1977-06-24 | Nicholas Ind Ltd | PREPARATION OF ETHYLAMINE DERIVATIVES |
| EP0356035A3 (en) * | 1988-08-12 | 1991-04-03 | Astra Aktiebolag | Arylkalkyl-amines and -amides having anticonvulsant and neuroprotective properties |
| WO1991011995A1 (en) * | 1988-08-12 | 1991-08-22 | Fisons Corporation | Arylalkyl-amines and -amides having anticonvulsant and neuroprotective properties |
| AU654802B2 (en) * | 1988-08-12 | 1994-11-24 | Astra Aktiebolag | Arylalkyl-amines and -amides having anticonvulsant and neuroprotective properties |
Also Published As
| Publication number | Publication date |
|---|---|
| NL128079C (en) | |
| FR465M (en) | 1961-05-02 |
| NL237722A (en) | |
| BE577279A (en) | 1959-10-01 |
| DK104116C (en) | 1966-04-04 |
| CH391186A (en) | 1965-04-30 |
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