US5266599A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Use of (+)-1-[(3,4,5-trimethoxy)-benzyloxymethyl]-1-phenyl-N,N-dimethyl-n-propylamine to increase gastric discharge in a subject
Assignee: Jouveinal SA
•
Filing: 1992-08-19
•
Granted: 1993-11-30
•
Expires: 2012-08-19
Abstract
Abstract (+)-1-[(3,4,5-trimethoxy)-benzyloxymethyl]-1-phenyl-N,N-dimethyl-n-pro pylamine of formula <IMAGE> is a medicament of use in gastroenterology.
Inventors
- 👤 Gilbert G. Aubard
- 👤 Alain P. Calvet
- 👤 Agnes Grouhel
- 👤 Henri Jacobelli
- 👤 Jean-Louis Junien
- 👤 Xavier B. Pascaud
- 👤 Francois J. Roman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 00:39
CPC Classifications
C; C07; C07C; C07C217/00; C07C217/02; C07C217/48
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
40 words
A method of stimulating gastric emptying in an animal in the essential absence of any analgesic effect which comprises administering to an animal an effective dosage of crystallized (+)-1-[(3,4,5-trimethoxy)-benzyloxymethyl]-1-phenyl-N,N-dimethyl-N-propylamine having the formula ##STR4## or its pharmaceutically acceptable acid addition salt.
Claim 2
Independent Claim
40 words
A method of stimulating gastric emptying in an animal in the essential absence of any analgesic effect which comprises administering to an animal an effective dosage of crystallized (+)-1-[(3,4,5-trimethoxy)-benzyloxymethyl]-1-phenyl-N,N-dimethyl-N-propylamine having the formula ##STR4## or its pharmaceutically acceptable acid addition salt.
Claim 3
Dependent Claim
11 words
The method of claim 1 wherein the salt is (+)-1-[(3,4,5-trimethoxy)-benzyloxymethyl]-1-phenyl-N,N-dimethyl-N-propylamine D-(-)-tartrate.
Claim 4
Dependent Claim
42 words
A process for normalizing the gastrointestinal tract of a patient treated with an analgesic compound comprising administering to said patient in an amount effective to normalize the gastrointestinal tract crystallized (+)-1-[(3,4,5-trimethoxy)-benzyloxymethyl]-1-phenyl-N,N-dimethyl-N-propylamine having the formula ##STR5## or its pharmaceutically acceptable acid addition salt.
Claim 5
Dependent Claim
42 words
A process for normalizing the gastrointestinal tract of a patient treated with an analgesic compound comprising administering to said patient in an amount effective to normalize the gastrointestinal tract crystallized (+)-1-[(3,4,5-trimethoxy)-benzyloxymethyl]-1-phenyl-N,N-dimethyl-N-propylamine having the formula ##STR5## or its pharmaceutically acceptable acid addition salt.
Claim 6
Independent Claim
68 words
A method for increasing gastric discharge in a subject which comprises administering to the subject a medicament consisting essentially of the (+) enantiomer of 1-[(3,4,5-trimethoxy)-benzyloxymethyl]-1-phenyl-N,N-dimethyl-n-propylamine or a pharmaceutically acceptable acid addition salt thereof in a crystallized form and in an amount which is therapeutically effective to increase the gastric discharge of solids from the subject and to provide antispasmodic activity while substantially avoiding the generation of analgesic activity.
Claim 7
Independent Claim
68 words
A method for increasing gastric discharge in a subject which comprises administering to the subject a medicament consisting essentially of the (+) enantiomer of 1-[(3,4,5-trimethoxy)-benzyloxymethyl]-1-phenyl-N,N-dimethyl-n-propylamine or a pharmaceutically acceptable acid addition salt thereof in a crystallized form and in an amount which is therapeutically effective to increase the gastric discharge of solids from the subject and to provide antispasmodic activity while substantially avoiding the generation of analgesic activity.
Claim 8
Dependent Claim
24 words
The method of claim 4 which further comprises forming the acid addition salt by reaction with an optically active enantiomer of an organic acid.
Claim 9
Dependent Claim
18 words
The method of claim 4 which further comprises forming the acid addition salt by reaction with D(-)tartaric acid.
Claim 10
Dependent Claim
28 words
The method of claim 4 which further comprises preparing the (+) enantiomer by forming a metallic alcoholate of (+)-2-dimethylamino-2-phenyl-n-butanol and condensing the alcoholate with a 3,4,5-trimethoxy benzyl halide.
Claim 11
Dependent Claim
53 words
The method of claim 4 which further comprises preparing the (+) enantiomer by forming diastereomers of racemic 1-[(3,4,5-trimethoxy-benzyloxymethyl]-1-phenyl-N,N-dimethyl-n-propylamine with a (+) enantiomer of an organic acid, removing the (-) enantiomer of the amine by crystallization and separation from the remaining filtrate and treating the filtrate to obtain the (+) enantiomer of the amine.
Claim 12
Dependent Claim
50 words
The method of claim 4 which further comprises preparing the (+) enantiomer by forming diastereomers of racemic 1-(3,4,5-trimethoxy)-benzyloxymethyl]-1-phenyl-N,N-dimethyl-n-propylamine with a L-(+)-tartaric acid, removing the (-) enantiomer of the amine by crystallization and subsequent separation from the remaining filtrate and treating the filtrate to obtain the (+) enantiomer of the amine.
Claim 13
Independent Claim
32 words
The method of one of claims 7, 8 or 9 which further comprises forming the acid addition salt by reaction with D(-)tartaric acid to purify the (+) enantiomer salt of the amine.
Claim 14
Dependent Claim
27 words
The method of claim 4 which further comprises administering the medicament at a daily therapeutic dose of between about 5 and 1000 mg of the (+) enantiomer.
Claim 15
Dependent Claim
22 words
The method of claim 4 which further comprises preparing the medicament in the form of a tablet, capsule, suppository, solution or suspension.
Claim 16
Dependent Claim
21 words
The method of claim 12 wherein the (+) enantiomer constitutes at least about 5 to 80% by weight of the medicament.
Claim 17
Dependent Claim
32 words
The method of claim 12 wherein the medicament is in the form of an aqueous solution or suspension with the (+) enantiomer constitutes at least about 0.1 to 20% by weight thereof.
Claim 18
Dependent Claim
50 words
The method of claim 4 wherein the gastric discharge is increased by at least about 4 times as much as the corresponding (-) enantiomer of the amine and wherein the D 50 toxicity of the (+) enantiomer is less than one-half that of the corresponding (-) enantiomer of the amine.
Claim 19
Independent Claim
91 words
A method for normalizing the activity of the gastrointestinal tract of a subject who has been treated with analgesic compounds, which comprises administering to the subject a medicament consisting essentially of the (+) enantiomer of 1-[(3,4,5-trimethoxy)-benzyloxymethyl]-1-phenyl-N,N-dimethyl-n-propylamine or a pharmaceutically acceptable acid addition salt thereof in a crystallized form and in an amount which is therapeutically effective to increase the gastric discharge of solids from the subject and to provide antispasmodic activity so that the effects of the analgesic compounds are reduced and the gastrointestinal tract activity is substantially returned to normal.
Claim 20
Independent Claim
91 words
A method for normalizing the activity of the gastrointestinal tract of a subject who has been treated with analgesic compounds, which comprises administering to the subject a medicament consisting essentially of the (+) enantiomer of 1-[(3,4,5-trimethoxy)-benzyloxymethyl]-1-phenyl-N,N-dimethyl-n-propylamine or a pharmaceutically acceptable acid addition salt thereof in a crystallized form and in an amount which is therapeutically effective to increase the gastric discharge of solids from the subject and to provide antispasmodic activity so that the effects of the analgesic compounds are reduced and the gastrointestinal tract activity is substantially returned to normal.
Claim 21
Dependent Claim
24 words
The method of claim 16 which further comprises forming the acid addition salt by reaction with an optically active enantiomer of an organic acid.
Claim 22
Dependent Claim
18 words
The method of claim 16 which further comprises forming the acid addition salt by reaction with D(-)tartaric acid.
Claim 23
Dependent Claim
28 words
The method of claim 16 which further comprises preparing the (+) enantiomer by forming a metallic alcoholate of (+)-2-dimethylamine-2-phenyl-n-butanol and condensing the alcoholate with a 3,4,5-trimethoxy benzyl halide.
Claim 24
Dependent Claim
53 words
The method of claim 16 which further comprises preparing the (+) enantiomer by forming diastereomers of racemic 1-[(3,4,5-trimethoxy)-benzyloxymethyl]-1-phenyl-N,N-dimethyl-n-propylamine with a (+) enantiomer of an organic acid, removing the (-) enantiomer of the amine by crystallization and separation from the remaining filtrate and treating the filtrate to obtain the (+) enantiomer of the amine.
Claim 25
Dependent Claim
50 words
The method of claim 16 which further comprises preparing the (+) enantiomer by forming diastereomers of racemic 1-[(3,4,5-trimethoxy)-benzyloxymethyl]-1-phenyl-N,N-dimethyl-n-propylamine with a L-(+)-tartaric acid, removing the (-) enantiomer of the amine by crystallization and subsequent separation from the remaining filtrate and treating the filtrate to obtain the (+) enantiomer of the amine.
Claim 26
Independent Claim
32 words
The method of one of claims 19, 20 or 21 which further comprises forming the acid addition salt by reaction with D(-)tartaric acid to purify the (+) enantiomer salt of the amine.
Claim 27
Dependent Claim
27 words
The method of claim 16 which further comprises administering the medicament at a daily therapeutic dose of between about 5 and 1000 mg of the (+) enantiomer.
Claim 28
Dependent Claim
22 words
The method of claim 23 which further comprises preparing the medicament in the form of a tablet, capsule, suppository, solution or suspension.
Claim 29
Dependent Claim
21 words
The method of claim 24 wherein the (+) enantiomer constitutes at least about 5 to 80% by weight of the medicament.
Claim 30
Dependent Claim
32 words
The method of claim 24 wherein the medicament is in the form of an aqueous solution or suspension with the (+) enantiomer constitutes at least about 0.1 to 20% by weight thereof.
Claim 31
Dependent Claim
50 words
The method of claim 16 wherein the gastric discharge is increased by at least about 4 times as much as the corresponding (-) enantiomer of the amine and wherein the D 50 toxicity of the (+) enantiomer is less than one-half that of the corresponding (-) enantiomer of the amine.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1996-11-29 | 1997-05-31 | 1997-11-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-11-29 | 2001-05-31 | 2001-11-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-11-29 | 2005-05-31 | 2005-11-30 | $7700.00 | Window Closed / Lapsed |