Claims
- 1. A process for preparing a pyrrolo[1,2-a]-azepinone of the formula: ##STR15## in which R.sub.3 denotes hydrogen or halogen, and either
- (A) R denotes benzyl or phenylthio in each of which the phenyl is unsubstituted or substituted by a halogen, hydroxy, alkyl, alkyloxy or alkylthio, and R.sub.1 and R.sub.2, which may be identical or different, each denote alkyl which is unsubstituted or sustituted by a dialkylamino in which the alkyls are separate or are joined to form, with the nitrogen atom to which they are linked, 1-pyrrolidinyl, piperidino, morpholino or 1-piperazinyl substituted by an alkyl, or alternatively R.sub.1 and R.sub.2 form, together with the nitrogen atom to which they are linked, 1-pyrrolidinyl, piperidino, morpholino or 1-piperazinyl, substituted by an alkyl, alkenyl of 2 to 4 carbon atoms, benzyl or phenethyl, the phenyl portions of the said benzyl or phenethyl being unsubstituted or substituted by a halogen, alkyl, alkyloxy, alkylthio, trifluoromethyl, carboxy, carboxylalkyl, alkyloxycarbony, alkyloxycarbonylalkyl, hydroxyalkyl, or alkylcarbonyloxyalkyl in which the alkylcarbonyl portion contains 2 to 18 carbon atoms in a straight or branched chain, or
- (B) R denotes phenyl or phenyl substituted by a halogen, hydroxy, alkyl, alkyloxy or alkylthio, and R.sub.1 and R.sub.2 form, together with the nitrogen atom to which they are linked, a piperazino or homopiperazino ring substituted by,
- an alkenyl of 2 to 4 carbon atoms, or
- a benzyl or phenethyl in each of which the phenyl portion is unsubstituted or substituted by a halogen, alkyl alkyloxy, alkylthio, trifluoromethyl, carboxy, carboxyalkyl, alkyloxycarbonyl, alkyloxycarbonylalkyl, hydroxyalkyl, or alkylcarbonyloxyalkyl in which the alkylcarbonyl portion contains 2 to 18 carbon atoms in a straight or branched chain, the aforesaid alkyl radicals and alkyl portions containing, except where otherwise stated, 1 to 4 carbon atoms each in a straight or branched chain, and the pharmaceutically acceptable salts thereof, which comprises rearranging a compound of the formula: ##STR16## in which the symbols R and R.sub.3 are as defined above and R.sub.1 and R.sub.2 are as defined above except that they do not form, with the nitrogen atom to which they are linked, a piperazino or homopiperazino ring substituted by a benzyl or phenethyl in each of which the phenyl is substituted by a carboxy, carboxyalkyl, hydroxyalkyl or alkylcarbonyloxyalkyl in which the alkylcarbonyl contains 2 to 18 carbon atoms in a straight or branched chain, to produce a compound of formula (I) in which the symbols are as defined above, except that R.sub.1 and R.sub.2 do not form, with the nitrogen atom to which they are linked, a piperazino or homopiperazino ring substituted by a benzyl or phenethyl in each of which the phenyl is substituted by a carboxy, carboxyalkyl, hydroxyalkyl, or alkylcarbonyloxyalkyl in which the alkylcarbonyl contains 2 to 18 carbon atoms is a straight or branched chain: isolating the product obtained andt then, if a product of formula (I) in which R and R.sub.3 are as defined above and R.sub.1 and R.sub.2 form, with the nitrogen atom to which they are linked, a piperazino or homopiperazino ring substituted by a benzyl or phenethyl in each of which the phenyl is substituted by a carboxy, carboxyalkyl or hydroxyalkyl is required, converting the corresponding product of formula (I), in which R and R.sub.3 are as defined above and R.sub.1 and R.sub.2 form, with the nitrogen atom to which they are linked, a piperazino or homopiperazino ring substituted by a benzyl or phenethyl in each of which the phenyl is substituted by an alkyloxycarbonyl or alkyloxycarbonylalkyl, into a corresponding acid or alcohol, and if required, acylating the alcohol obtained to produce a product of formula (I) in which R and R.sub.3 are as defined above and R.sub.1 and R.sub.2 form, with the nitrogen atom to which they are linked, a piperazino or homopiperazino ring substituted by a benzyl or phenethyl in each of which the phenyl is substituted by an alkylcarbonyloxyalkyl in which the alkylcarbonyl contains 2 to 18 carbon atoms in a straight or branched chain:
- and isolating the product and if required converting it into a pharmaceutically acceptable salt."
Priority Claims (1)
Number |
Date |
Country |
Kind |
8503840 |
Mar 1985 |
FRX |
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Parent Case Info
This is a division of application Ser. No. 839,101, filed Mar. 13, 1986, now U.S. Pat. No. 4,769,366.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
3239528 |
Bebenburg et al. |
Mar 1966 |
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4148895 |
Lattrell et al. |
Apr 1979 |
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Non-Patent Literature Citations (2)
Entry |
Jones et al., CA97-23610r, "Azonia-azulene Salts", Part 5, Synthesis of 5H-pyrrolo[1,2-a]azepine and of 7H-pyrrolo-[1,2-a]azepine-7-one. |
Jones et al., J. C. S. Perkin I, 1982, (4), pp. 1123-1130. |
Divisions (1)
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Number |
Date |
Country |
Parent |
839101 |
Mar 1986 |
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