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Generated: August 17, 2017

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Title: Process and intermediates for manufacture of 3-(5-amino-1-carboxypentylamino)-tetrahydro-1-benzazepin-2-one-1-acetic acid
Abstract:The invention concerns a novel process for the preparation of 3-(5-amino-1-carboxypentylamino)-tetrahydro-1-benzazepin-2-one-1-acetic acid by opening, preferably under acidic conditions, the caprolactam ring in a compound of formula II ##STR1## wherein COR represents carboxy or esterified carboxy, and hydrolyzing the esterified carboxy group if present. The preparation of the starting materials of formula II is described.
Inventor(s): Bach; Joseph (Parsippany, NJ), Boyer; Stephen K. (Far Hills, NJ)
Assignee: Ciba-Geigy Corporation (Ardsley, NY)
Filing Date:Oct 18, 1984
Application Number:06/662,313
Claims:1. A process for the preparation of a compound of the formula ##STR7## wherein R.sup.1 represents 4-aminobutyl, COR.sup.2 and COR.sup.3 represent carboxy; or a pharmaceutically acceptable salt thereof; which comprises ring opening the monocyclic lactam in a compound of the formula ##STR8## wherein COR represents carboxy or esterified carboxy, and hydrolysis of the esterified carboxy group when COR represents esterified carboxy; esterified carboxy comprising lower alkoxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl substituted in the phenyl ring by lower alkyl, halogen or lower alkoxy, or pyridylmethoxycarbonyl.

2. A process according to claim 1 wherein COR in a compound of formula II represents carboxy or lower alkoxycarbonyl.

3. A process according to claim 1 carried out under acidic conditions.

4. A process according to claim 1 carried out with a mineral acid, a lower alkylsulfonic acid or an acidic ion exchange resin.

5. A process according to claim 1 carried out with a mineral acid.

6. A process according to claim 1 carried out with an acidic ion exchange resin.

7. A process according to claim 1 for the preparation of the compound of the formula Ia ##STR9## wherein R.sup.1 represents 4-aminobutyl, COR.sup.2 and COR.sup.3 represent carboxy; or a pharmaceutically acceptable salt thereof; which comprises ring opening the monocyclic lactam in a compound of formula IIa ##STR10## wherein COR represents carboxy or esterified carboxy, as defined in claim 1 and hydrolysis of the esterified carboxy group when COR represents esterified carboxy.

8. A process according to claim 7 wherein COR in a compound of formula IIa represents carboxy or lower alkoxycarbonyl.

9. A process, according to claim 1 for the preparation of 3-[(5-amino-1-carboxy-(1S)-pentyl)amino]-1-carboxymethyl-2,3,4,5-tetrahydr o-1H-1-(3S)-benzazepin-2-one or a pharmaceutically acceptable salt thereof, which comprises reacting 1-ethoxycarbonylmethyl-3-[(2-oxo-(3S)-hexahydro-1H-azepin-3-yl)-amino]-2,3 ,4,5-tetrahydro-1H-1-(3S)-benzazepin-2-one with a strong mineral acid.

10. A process according to claim 9 carried out with aqueous hydrochloric acid.

11. A process according to claim 9 carried out with aqueous hydrochloric acid at elevated temperature.

12. A compound of the formula ##STR11## wherein COR represents carboxy; or COR represents esterified carboxy comprising lower alkoxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl substituted in the phenyl ring by lower alkyl, halogen or lower alkoxy, or pyridylmethoxycarbonyl; or an acceptable salt thereof.

13. A compound according to claim 12 wherein COR represents carboxy or lower alkoxycarbonyl; or an acceptable salt thereof.

14. A compound according to claim 12 of the formula ##STR12## wherein COR represents carboxy or esterified carboxy; as defined in claim 12 or an acceptable salt thereof.

15. A compound according to claim 14 wherein COR represents carboxy or lower alkoxycarbonyl; or an acceptable salt thereof.

16. A compound according to claim 15, wherein COR in formula IIa is ethoxycarbonyl, being 1-ethoxycarbonylmethyl-3-[(2-oxo-(3S)-hexahydro-1H-azepin-3-yl)-amino]-2,3 ,4,5-tetrahydro-1H-1-(3S)-benzazepin-2-one; or an acid addition salt thereof.
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