US5266599A — Use of (+)-1-[(3,4,5-trimethoxy)-benzyloxymethyl]…

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.

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

Use of (+)-1-[(3,4,5-trimethoxy)-benzyloxymethyl]-1-phenyl-N,N-dimethyl-n-propylamine to increase gastric discharge in a subject

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