US3642993A - Pharmaceutical composition containing 2-methyl - 5 - phenyl - 1 2-dihydro-3h-2-benzazepine for treatment of a condition associated with anxiety or tension - Google Patents
Pharmaceutical composition containing 2-methyl - 5 - phenyl - 1 2-dihydro-3h-2-benzazepine for treatment of a condition associated with anxiety or tension Download PDFInfo
- Publication number
- US3642993A US3642993A US16961A US3642993DA US3642993A US 3642993 A US3642993 A US 3642993A US 16961 A US16961 A US 16961A US 3642993D A US3642993D A US 3642993DA US 3642993 A US3642993 A US 3642993A
- Authority
- US
- United States
- Prior art keywords
- methyl
- benzazepine
- anxiety
- dihydro
- tension
- 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 - Lifetime
Links
- 208000019901 Anxiety disease Diseases 0.000 title abstract description 6
- 230000036506 anxiety Effects 0.000 title abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 5
- 239000000203 mixture Substances 0.000 abstract description 16
- 150000003839 salts Chemical class 0.000 abstract description 8
- 239000003937 drug carrier Substances 0.000 abstract description 6
- 230000004970 emotional disturbance Effects 0.000 abstract description 5
- -1 2-METHYL-5PHENYL-1,2-DIHYDRO-3H-BENZAZEPINE Chemical compound 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 20
- 239000002775 capsule Substances 0.000 description 8
- 239000008187 granular material Substances 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 239000006188 syrup Substances 0.000 description 5
- 235000020357 syrup Nutrition 0.000 description 5
- 229920002261 Corn starch Polymers 0.000 description 4
- 235000019759 Maize starch Nutrition 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 229960002216 methylparaben Drugs 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 2
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 235000012735 amaranth Nutrition 0.000 description 1
- 239000004178 amaranth Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- CEYULKASIQJZGP-UHFFFAOYSA-L disodium;2-(carboxymethyl)-2-hydroxybutanedioate Chemical compound [Na+].[Na+].[O-]C(=O)CC(O)(C(=O)O)CC([O-])=O CEYULKASIQJZGP-UHFFFAOYSA-L 0.000 description 1
- YGLLICRFEVEWOZ-UHFFFAOYSA-L disodium;3-carboxy-1-[(3-carboxy-2-oxidonaphthalen-1-yl)methyl]naphthalen-2-olate Chemical compound [Na+].[Na+].C1=CC=C2C(CC3=C4C=CC=CC4=CC(=C3O)C([O-])=O)=C(O)C(C([O-])=O)=CC2=C1 YGLLICRFEVEWOZ-UHFFFAOYSA-L 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 239000006215 rectal suppository Substances 0.000 description 1
- 229940100618 rectal suppository Drugs 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 230000004799 sedative–hypnotic effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- UJMBCXLDXJUMFB-GLCFPVLVSA-K tartrazine Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-GLCFPVLVSA-K 0.000 description 1
- 235000012756 tartrazine Nutrition 0.000 description 1
- 239000004149 tartrazine Substances 0.000 description 1
- 229960000943 tartrazine Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
Definitions
- the utility of the composition is to relieve conditions associated with anxiety, tension or the emotional disturbances.
- This invention relates to therapeutic compositions.
- non-toxic pharmaceutically acceptable salts thereof have a useful effect on the central nervous system.
- they have a sedative-hypnotic efi'ect and may be used in the treatment of conditions associated with anxiety, tension or other emotional disturbances.
- mice and rats In small animal species such as mice and rats the administration of an oral dose of 2550 mg. in the form of the hydrochloride produced moderate to marked depression which was devoid of associated stimulant activity, the duration of action exceeding 4 hours.
- the invention therefore provides a pharmaceutical composition
- a pharmaceutical composition comprising a compound of Formula I above, or a non-toxic pharmaceutically acceptable salt in association with a pharmaceutical carrier.
- pharmaceutical carrier does not extend to common solvents as normally used but is intended to extend to such solvents when they have been particularly adapted for pharmaceutical use, for example by being rendered sterile or non-pyrogenic. It is also to be made clear that the invention extends to such solvents when they are used in a particular form for administration such as in capsules and the like.
- compositions may be prepared by techniques well known in the pharmaceutical art. Suitable dosage forms include capsules pressed or coated, tablets, syrups and aqueous suspensions. The compositions may also be presented in rectal suppository form. They may alsocontain other active ingredients. Preferably the composition is in unit dosage form which expression as used herein means a physically discrete unit containing a predetermined dose of the active ingredient in association with a ice pharmaceutically acceptable carrier or excipient. The unit dosage form may contain from 25-500 mg. of the active ingredient.
- the daily dose of the active ingredient may be from 0.5 mg./kg. 20 mg./ kg. depending on the clinical state of patient and response to therapy.
- the compound may be prepared by methods described by Harcourt and Brooks in J. Chem. Soc. 1969 (C) 625.
- the salts may be made from the base or from other salts by conventional methods.
- EXAMPLE 1 Capsules To prepare 10,000 capsules each containing 5 mg. of Compound I.Mix together 50 g. Compound I and 850 g. of dried micro-crystalline cellulose B.-P.C. Fill the powder into hard gelatin capsules size No. 4 so that each capsule contains mg. of the mixture.
- the tablets may be film coated or sugar coated if required.
- the tablets may be film coated or sugar coated if required.
- a pharmaceutical composition for relieving a condition associated with anxiety, tension or the like emotional disturbances comprising in unit dosage form from -500 mg. of 2-methyl-5-phenyl-1,Z-dihydro-3H-2-benzazepine, or a pharmaceutically acceptable salt thereof, in association with a pharmaceutical carrier.
- composition as claimed in claim 1 in the form of a pressed or coated capsule, a tablet, a syrup or an aqueous suspension.
- a method of treating a patient to relieve a condition associated with anxiety, tension or like emotional disturbances which comprises administering to said )patient an effective dose of 2rmethyl-5-phenyl-l,2;-dihydro-3H-2-benzazepine or a pharmaceutically acceptable salt thereof.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A PHARMACEUTICAL COMPOSITION COMPRISING 2-METHYL-5PHENYL-1,2-DIHYDRO-3H-BENZAZEPINE, OR A PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, IN ASSOCIATION WITH A PHARMACEUTICAL CARRIER. THE UTILITY OF THE COMPOSITION IS TO RELIEVE CONDITIONS ASSOCIATED WITH ANXIETY, TENSION OR THE EMOTIONAL DISTURBANCES.
Description
United States Patent 36,028/ 69 Int. Cl. A61v 27/00 US. Cl. 424--244 4 Claims ABSTRACT OF THE DISCLOSURE A pharmaceutical composition comprising 2-methyl-5- phenyl-1,2-dihydro-3H-benzazepine, or a pharmaceutically acceptable salt thereof, in association with a pharmaceutical carrier.
The utility of the composition is to relieve conditions associated with anxiety, tension or the emotional disturbances.
This invention relates to therapeutic compositions. We have found, according to the invention, that 2- methyl 5 phenyl-1,2-dihydro-3H-Z-benzazepine of the formula:
and non-toxic pharmaceutically acceptable salts thereof have a useful effect on the central nervous system. In particular they have a sedative-hypnotic efi'ect and may be used in the treatment of conditions associated with anxiety, tension or other emotional disturbances.
In small animal species such as mice and rats the administration of an oral dose of 2550 mg. in the form of the hydrochloride produced moderate to marked depression which was devoid of associated stimulant activity, the duration of action exceeding 4 hours.
The invention therefore provides a pharmaceutical composition comprising a compound of Formula I above, or a non-toxic pharmaceutically acceptable salt in association with a pharmaceutical carrier.
The term pharmaceutical carrier as used herein does not extend to common solvents as normally used but is intended to extend to such solvents when they have been particularly adapted for pharmaceutical use, for example by being rendered sterile or non-pyrogenic. It is also to be made clear that the invention extends to such solvents when they are used in a particular form for administration such as in capsules and the like.
The compositions may be prepared by techniques well known in the pharmaceutical art. Suitable dosage forms include capsules pressed or coated, tablets, syrups and aqueous suspensions. The compositions may also be presented in rectal suppository form. They may alsocontain other active ingredients. Preferably the composition is in unit dosage form which expression as used herein means a physically discrete unit containing a predetermined dose of the active ingredient in association with a ice pharmaceutically acceptable carrier or excipient. The unit dosage form may contain from 25-500 mg. of the active ingredient.
The daily dose of the active ingredient may be from 0.5 mg./kg. 20 mg./ kg. depending on the clinical state of patient and response to therapy.
The compound may be prepared by methods described by Harcourt and Brooks in J. Chem. Soc. 1969 (C) 625. The salts may be made from the base or from other salts by conventional methods.
The following examples illustrate the invention (where reference is made to Compound I this is the compound of Formula I above).
EXAMPLE 1 Capsules To prepare 10,000 capsules each containing 5 mg. of Compound I.Mix together 50 g. Compound I and 850 g. of dried micro-crystalline cellulose B.-P.C. Fill the powder into hard gelatin capsules size No. 4 so that each capsule contains mg. of the mixture.
To prepare 10,000 capsules each containing 10 mg. of Compound I.Mix together g. Compound I and 1,100 g. of dried micro-crystalline cellulose B.P.C. Fill the powder into hard gelatin capsules size No. 3 so that each capsule contains mg. of the mixture.
EXAMPLE 2 Tablets To prepare 20,000 tablets each containing 50 mg. of Compound I.--Mix together 1 kg. Compound I, 2.47 kg. of lactose and 250 g. of maize starch and suflicient of a 1% aqueous solution of sodium carboxymethylcellulose to produce a damp cohesive mass. Granulate the damp mass by passing through a suitable comminuting mill and dry the granules at 50 C. in a fluidised bed dryer. Mix the dried granules with 250 g. of dried maize starch and 30 g. of magnesium stearate. Compress the lubricated granules on a suitable tableting machine to produce biconvex tablets in diameter and each weighing about 200 mg.
The tablets may be film coated or sugar coated if required.
To prepare 20,000 tablets each containing 200 mg. of Compound I.-Mix together 4.0 kg. compound I, 2.9 kg. lactose and 500 g. of maize starch and suflicient of a 1% aqueous solution of sodium carboxymethylcellulose to produce a damp cohesive mass. Granulate the damp mass by passing through a suitable comminuting mill and dry the granules at 50 C. in a fluidised bed dryer. and 50 g. magnesium stearate. Compress the lubricated Mix the dried granules with 500 g. of dried maize starch granules on a suitable tableting machine to produce biconvex in diameter and each weighing about 400 mg.
The tablets may be film coated or sugar coated if required.
EXAMPLE 3 Syrup To prepare a syrup suitable for oral administration containing Compound I HCl equivalent to 100 mg. of Compound I per 5 ml.--Heat 6 litres of distilled water to 70 C. and in it dissolve 15 g. of methyl parahydroxybenzoate and 2 g. of propyl parahydroxybenzoate followed by 5 kg. of sucrose. Cool the syrup to 40 C. and dissolve 3 g. of sodium saccharin, 50 g. of citric acid, 20 g. of sodium acid citrate, 30 ml. of lemon flavour, 10 g. of tartrazine and 231 g. of compound I, HCl. When solution is complete make up to 10 litres with distilled water.
3 EXAMPLE 4 Suspension To prepare an aqueous suspension suitable for oral administration containing Compound I pamoate equivalent to 50 mg. of Compound I per 5 ml.--Dissolve 100 g. of compound I in 1 litre of distilled water by the addition of the requisite amount of hydrochloric acid. In a separate litre of water dissolve 160 g. of disodium pamoate. Mix together these two solutions to produce a suspension of Compound I pamoate.
Heat to 70 C. 6 litres of distilled water and in it dissolve 15 g. of methyl parahydroxybenzoate and 2 g. of propyl parahydroxybenzoate. Mix together 4 kg. of sucrose and 20 g. of Carbopol 934 and add this to the hot solution prepared earlier. When the sucrose has dissolved and the Carbopol has been well dispersed add sufiicient of a freshly prepared 10% aqueous solution of sodium hydroxide to raise the pH to 7.0. Continue stirring until a smooth gel has formed ensuring that the stirrer does not entrain any air into the gel. Cool the gel to 40 C. and carefully dissolve in the gel 30 ml. of a suitable flavour and 5 g. of amaranth. Add the suspension of Compound I pamoate and mix carefully until a homogeneous product has been produced. Make up to 10 litres with further distilled water.
What is claimed is:
1. A pharmaceutical composition for relieving a condition associated with anxiety, tension or the like emotional disturbances comprising in unit dosage form from -500 mg. of 2-methyl-5-phenyl-1,Z-dihydro-3H-2-benzazepine, or a pharmaceutically acceptable salt thereof, in association with a pharmaceutical carrier.
2. A composition as claimed in claim 1 in the form of a pressed or coated capsule, a tablet, a syrup or an aqueous suspension.
3. A method of treating a patient to relieve a condition associated with anxiety, tension or like emotional disturbances which comprises administering to said )patient an effective dose of 2rmethyl-5-phenyl-l,2;-dihydro-3H-2-benzazepine or a pharmaceutically acceptable salt thereof.
4. A method as claimed in claim 3 in which the dose is given in the form of unit dose, each dose containing from 25-500 mg. of active ingredient to provide a daily dose of from 05-20 mg./kg. body weight.
References Cited J. Chem. Soc., 1969 (C), PP. 625-627.
STANLEY J. FRIEDMAN, Primary Examiner
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB36028/69A GB1242963A (en) | 1969-07-17 | 1969-07-17 | Novel benzazepine derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3642993A true US3642993A (en) | 1972-02-15 |
Family
ID=10384167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US16961A Expired - Lifetime US3642993A (en) | 1969-07-17 | 1970-03-05 | Pharmaceutical composition containing 2-methyl - 5 - phenyl - 1 2-dihydro-3h-2-benzazepine for treatment of a condition associated with anxiety or tension |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3642993A (en) |
| BE (1) | BE747121A (en) |
| FR (1) | FR2054638B1 (en) |
| NL (1) | NL7003348A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070021408A1 (en) * | 2005-07-15 | 2007-01-25 | Amr Technology, Inc. | Aryl-and heteroaryl-substituted tetrahydrobenzazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3225031A (en) * | 1963-07-22 | 1965-12-21 | Schering Corp | Phenyl-benzazepines and methods for their manufacture |
-
1970
- 1970-03-05 US US16961A patent/US3642993A/en not_active Expired - Lifetime
- 1970-03-09 NL NL7003348A patent/NL7003348A/xx unknown
- 1970-03-10 FR FR707008513A patent/FR2054638B1/fr not_active Expired
- 1970-03-10 BE BE747121D patent/BE747121A/en unknown
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070021408A1 (en) * | 2005-07-15 | 2007-01-25 | Amr Technology, Inc. | Aryl-and heteroaryl-substituted tetrahydrobenzazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| WO2007011820A2 (en) | 2005-07-15 | 2007-01-25 | Amr Technology, Inc. | Aryl-and heteroaryl-substituted tetrahydrobenzazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| US20080207595A9 (en) * | 2005-07-15 | 2008-08-28 | Amr Technology, Inc. | Aryl-and heteroaryl-substituted tetrahydrobenzazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| US20110046114A1 (en) * | 2005-07-15 | 2011-02-24 | Albany Molecular Research, Inc. | Aryl- and heteroaryl-substituted tetrahydrobenzazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| US7956050B2 (en) | 2005-07-15 | 2011-06-07 | Albany Molecular Research, Inc. | Aryl- and heteroaryl-substituted tetrahydrobenzazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| US8791101B2 (en) | 2005-07-15 | 2014-07-29 | Albany Molecular Research, Inc. | Aryl- and heteroaryl-substituted tetrahydrobenzazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| US9403776B2 (en) | 2005-07-15 | 2016-08-02 | Albany Molecular Research, Inc. | Aryl- and heteroaryl-substituted tetrahydrobenzazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2054638A1 (en) | 1971-04-23 |
| FR2054638B1 (en) | 1973-08-10 |
| BE747121A (en) | 1970-09-10 |
| NL7003348A (en) | 1971-01-19 |
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