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Claims for Patent: 5,010,090

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Claims for Patent: 5,010,090

Title: N-(butenyl substituted) azaheterocyclic carboxylic acids
Abstract:1-Aminobut-3-en derivatives having optionally substituted furanyl, thienyl, pyridyl and/or pyrrolyl in the 4-position and 3-carboxypiperidin-1-yl, 3-carboxytetrahydropyrid-1-yl or 3 carboxymethylpyrrolidin-1-yl in the 1-position potentiate GABA-ergic neurotransmission.
Inventor(s): Gronvald; Frederik C. (Vedbaek, DK), Braestrup; Claus (Roskilde, DK)
Assignee: Novo Nordisk A/S. (Bagsvaerd, DK)
Application Number:07/254,557
Patent Claims: 1. A compound of formula I ##STR9## wherein R.sup.1 and R.sup.2 are the same or different and each represents a substituted or unsubstituted, thien-2-yl, thien-3-yl, pyrrol-2-yl or pyrrol-3-yl wherein the substitution is with at least one of C.sub.1-7 alkyl, bromo, chloro, or fluoro and at least one of said R.sup.1 and R.sup.2 is thien-2-yl substituted at least at the 3-position or pyrrol-2-yl substituted at least at the 1-position with C.sub.1-7 -alkyl, chloro, bromo, or fluoro, and wherein R.sup.3 represents 3-carboxypiperidin-1-yl, 3-carboxy-1,2,5,6-tetrahydropyridin-1-yl or 3-carboxymethylpyrrolidin-1-yl, and pharmaceutically acceptable salts thereof.

2. A compound of formula I ##STR10## wherein R.sup.1 is 3-methylthien-2-yl, R.sup.2 is 3-methylthien-2-yl and R.sup.1 is nipecotic acid, and pharmaceutically acceptable salts thereof.

3. A compound of formula I ##STR11## wherein R.sup.1 is thien-2-yl, R.sup.2 is 3-methylthien-2-yl and R.sup.3 is guvacine, and pharmaceutically acceptable salts thereof.

4. A compound of formula I ##STR12## wherein R.sup.1 is thien-2-yl, R.sup.2 is 3-methylthien-2-yl and R.sup.3 is nipecotic acid, and pharmaceutically acceptable salts thereof.

5. A compound of formula I ##STR13## wherein R.sup.1 is 3-methylthien-2-yl, R.sup.2 is 3-methylthien-2-yl and R.sup.3 is guvacine, and pharmaceutically acceptable salts thereof.

6. A compound according to the following formula ##STR14## wherein R.sup.1 and R.sup.2 are the same or different and each represents thienyl or pyrrolyl and wherein R.sup.3 represents 3-carboxypiperidin-1-yl, 3-carboxy-1,2,5,6-tetrahydropyridin-1-yl or 3-carboxymethylpyrrolidin-1-yl, selected from the following:

N-(4,4-Bis(3-methylthien-2-yl)but-3-enyl)guvacine,

N-(4,4-Bis(3-methylthien-2-yl)but-3-enyl)nipecotic acid,

N-(4,4-Bis(3-methylthien-2-yl)but-3-enyl)-.beta.-homoproline,

N-(4-(3-Methylthien-2-yl)-4-(thien-2-yl)but-3-enyl)guvacine,

N-(4-(3-Methylthien-2-yl)-4-(thien-2-yl)but-3-enyl)nipecotic acid,

N-(4-(3-Methylthien-2-yl)-4-(thien-2-yl)but-3-enyl)-.beta.-homoproline

N-(4-(N-methylpyrrol-2-yl)-4-(thien-2-yl)but-3-enyl)guvacine,

N-(4-(N-methylpyrrol-2-yl)-4-(thien-2-yl)but-3-enyl)nipecotic acid,

N-(4-(N-methylpyrrol-2-yl)-4-(thien-2-yl)but-3-enyl)-.beta.-homoproline,

N-(4,4-Bis(N-methylpyrrol-2-yl)but-3-enyl)guvacine,

N-(4,4-Bis(N-methylpyrrol-2-yl)but-3-enyl)nipecotic acid,

N-(4,4-Bis(N-methylpyrrol-2-yl)but-3-enyl)-.beta.-homoproline

N-(4-(3-Bromothien-2-yl)-4-(thien-2-yl)but-3-enyl)-nipecotic acid, and

pharmaceutically acceptable salts thereof.

7. A compound of formula I ##STR15## wherein R.sup.1 and R.sup.2 are the same or different and each represents thienyl, or pyrrolyl, and wherein R.sup.3 represents 3-carboxypiperdin-1-yl,3-carboxy-1,2,5,6-tetrahydropyridin-1-yl or 3-carboxymethyl-pyrrolidin-1-yl, selected from the following:

N-(4,4-Bis(3-Methylthien-2-yl)but-3-enyl)nipecotic acid,

N-(4,4-Bis(4-Methylthien-2-yl)but-3-enyl)nipecotic acid,

N-(4,4-Bis(5-Methylthien-2-yl)but-3-enyl)nipecotic acid,

N-(b 4-(3-Methylthien-2-yl)-4-(4-Methylthien-2-yl)but-3-enyl)nipecotic acid,

N-(4-(3-Methylthien-2-yl)-4-(4-Methylthien-2-yl)but-3-enyl)guvacine,

N-(4-(3-Methylthien-2-yl)-4-(thien-2-yl)but-3-enyl)nipecotic acid,

N-(4-(3-Methylthien-2-yl)-4-(4-thien-2-yl)but-3-enyl)guvacine,

N-(4,4-Bis(N-methylpyrrol-2-yl))but-3-enyl)nipecotic acid,

N-(4,4-Bis(5-chloro-4-methylpyrrol-2-yl))but-3-enyl)nipecotic acid,

N-(4-(3-Methylthien-2-yl)-4-(thien-2-yl)but-3-enyl)-.beta.-homoproline, and

pharmaceutically acceptable salts thereof.

8. Pharmaceutical compositions containing effective amounts of a compound according to the formula I ##STR16## wherein R.sup.1 and R.sup.2 are the same or different and each represents a substituted or unsubstituted thien-2-yl, thien-3-yl, pyrrol-2-yl or pyrrol-3-yl wherein the substitution is with at least one of C.sub.1-7 alkyl, bromo, chloro, or fluoro and at least one of said R.sup.1 and R.sup.2 is thien 2-yl substituted at least at the 3-position or pyrrol-2-yl substituted at least at the 1-position with C.sub.1-7 -alkyl, chloro bromo, or fluoro and wherein R.sup.3 represents 3-carboxypiperidin-1-yl, 3-carboxy-1,2,5,6-tetrahydropyridin-1-yl or 3-carboxymethyl-pyrrolidin-1-yl, and pharmaceutically acceptable salts thereof.

9. Compositions according to claim 8, characterized in that they contain therein a therapeutically effective dose of from about 25 mg to about 1 g of the compound.

10. A method of inhibiting uptake of .gamma.-amino butyric acid in a subject in need of such a treatment comprising the step of administering to said subject a therapeutically effective dose of a compound according to the formula ##STR17## wherein R.sup.1 and R.sup.2 are the same or different and each represents a substituted or unsubstituted thien-2-yl, thien-3-yl, pyrrol-2-yl or pyrrol-3-yl wherein the substitution is with at least one of C.sub.1-7 alkyl, bromo, chloro, or fluoro and at least one of said R.sup.1 and R.sup.2 is thien-2-yl substituted at least at the 3-position or pyrrol-2-yl substituted at least at the 1-position with C.sub.1-7 -alkyl, chloro, bromo, or fluoro and wherein R.sup.3 represents 3-carboxypiperidin-1-yl, 3-carboxy-1,2,5,6-tetrahydropyridin-l-yl or 3-carboxymethylpyrrolidin-1-yl, and pharmaceutically acceptable salts thereof.
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