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EP0470490A1 Expired / Lapsed EP ⏱️ 0.0 years remaining

Substituted pyrroles

Assignee: F Hoffmann La Roche AG
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Filing: 1991-07-30
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Granted: —
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Expires: 2011-07-30
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Abstract

Abstract Compounds of the formula wherein R 1 and R 3 together form a bond and R 2 represents hydrogen or R 1 and R 2 together form a bond and R 3 represents hydrogen; R 4 , R 5 , R 6 and R 7 each independently represent hydrogen, halogen, alkyl, haloalkyl, alkoxy, nitro, amino, alkanoylamino, aroylamino, alkylthio or alkylsulphonyl; R 8 represents hydrogen, alkyl or aralkyl; X represents -N(R 9 )- or -CHN(R 10 ,R 11 )- in which R 9 , R 10 and R 11 each represent hydrogen, alkyl, aralkyl or alkanoyl; m stands for 0-2 and n stands for 1-3, with the proviso that the sum of m and n is 1-3; p stands fo 0-4 and q stands for 0-4, with the proviso that the sum of p and q is 2-4 when X represents -N(R 9 )-, that the sum of p and q is 1-5 when X represents -CHN(R 10 ,R 11 )- and R 1 and R 2 together form a bond, that the sum of p and q is 0-4 when X represents -CHN(R 10 ,R 11 )- and R 1 and R 3 together form a bond and that p stands for 1-4 when X represents -N(R 9 )-, R 1 and R 3 together represent a bond and m stands for 0, as well as pharmaceutically acceptable salts of acidic compounds of formula I with bases and of basic compounds of formula I with acids, are useful in the control or prevention of inflammatory, immunological, oncological, bronchopulmonary, dermatological or cardiovascular disorders or for the treatment of asthma, AIDS or diabetic complications or for the stimulation of hair growth. They can be prepared from correspondingly substituted furandiones.

Inventors

  • 👤 Peter David Davis
  • 👤 Christopher Huw Hill
  • 👤 Geoffrey Lawton

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-04 10:30
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/12; C07D471/20; C07D471/02; C07D471/04; A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/435; A61P; A61P11/00; A61P11/08; A61P17/00; A61P29/00; A61P3/00; A61P3/08; A61P3/10; A61P31/00; A61P31/12; A61P31/14; A61P31/18; A61P35/00; A61P7/00; A61P7/02; A61P9/00; A61P9/08; A61P9/10; C07D471/10; C07D471/14

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 418 words
A process for the manufacture of compounds of the general formula wherein R 1 and R 3 together form a bond and R 2 represents hydrogen or R 1 and R 2 together form a bond and R 3 represents hydrogen; R 4 , R 5 , R 6 and R 7 each independently represent hydrogen, halogen, alkyl, haloalkyl, alkoxy, nitro, amino, alkanoylamino, aroylamino, alkylthio or alkylsulphonyl; R 8 represents hydrogen, alkyl or aralkyl; X represents -N(R 9 )- or -CHN(R 10 ,R 11 )- in which R 9 , R 10 and R11 each represent hydrogen, alkyl, aralkyl or alkanoyl; m stands for 0-2 and n stands for 1-3, with the proviso that the sum of m and n is 1-3; p stands for 0-4 and q stands for 0-4, with the proviso that the sum of p and q is 2-4 when X represents -N(R 9 )-, that the sum of p and q is 1-5 when X represents -CHN-(R 10 ,R 11 )- and R 1 and R 2 together form a bond, that the sum of p and q is 0-4 when X represents -CHN-(R 10 ,R 11 )- and R 1 and R 3 together form a bond and that p stands for 1-4 when X represents -N(R 9 )-, R 1 and R 3 together represent a bond and m stands for 0, as well as pharmaceutically acceptable salts of acidic compounds of formula I with bases and of basic compounds of formula I with acids, which process comprises (a) reacting a compound of the general formula wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , m, n, p and q have the significance given in claim 1 and X' represents -N(R 9' )- or -CHN(R 10' ,R 11' )- in which R 9 ', R 10' and R 11' each represent hydrogen, alkyl, aralkyl, alkanoyl, alkoxycarbonyl or aryloxycarbonyl, with ammonia under pressure or with hexamethyldisilazane and methanol and, where required, cleaving off any alkoxycarbonyl or aralkoxycarbonyl group(s) present in the reaction product, or (b) for the manufacture of a compound of formula I in which R 8 represents hydrogen, debenzylating a compound of formula I in which R 8 represents benzyl, (c) if desired, converting an acidic compound of formula I into a pharmaceutically acceptable salt with a base or converting a basic compound of formula I into a pharmaceutically acceptable salt with an acid.
Claim 2
Dependent Claim 36 words
A process according to claim 1, wherein R 1 and R 3 together form a bond and R 2 represents hydrogen, X represents -N(R 9 )- and m, n, p and q each stand for 1.
Claim 3
Dependent Claim 38 words
A process according to claim 1, wherein R 1 and R 2 together form a bond and R 3 represents hydrogen, X represents -N(R 9 )-, m, n and q stand for 1 and p stands for 2.
Claim 4
Dependent Claim 27 words
A process according to any one of claims 1 to 3, wherein R 4 , R 5 , R 6 , and R 7 each represent hydrogen.
Claim 5
Dependent Claim 18 words
A process according to any one of claims 1 to 4, wherein R 8 represents alkyl, preferably methyl.
Claim 6
Dependent Claim 22 words
A process according to any one of claims 1 to 5, wherein R 9 represents hydrogen or alkyl, preferably hydrogen or methyl.
Claim 7
Dependent Claim 29 words
A process according to claim 1 or any one of claims 4 to 6, wherein R 10 and R 11 each represent hydrogen or each represent alkyl, preferably methyl.
Claim 8
Dependent Claim 24 words
A process according to claim 1, wherein a product of the following group is prepared: 3-[6,7,8,9-Tetrahydrospiro[pyrido(1,2-a]indole-8,3'-pyrrolidin]-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione, cis-3-[2,3,3a,4,11,11 a-Hexahydro-2-methyl-1 H-pyrrolo[3',4':4,5]pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1 H-pyrrole-2,5-dione, trans-3-[2,3,3a,4,11,11 a-Hexahydro-2-methyl-1 H-pyrrolo[3',4':4,5]pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-l H-pyrrole-2,5-dione.
Claim 9
Dependent Claim 72 words
A process for the manufacture of a medicament, especially an antiinflammatory, immunological, oncological, bronchopulmonary, dermatological or cardiovascular medicament or a medicament for the treatment of asthma, AIDS or diabetic complications or for the stimulation of hair growth, which process comprises bringing a compound according to any one of claims 1-8 into a galenical administration form together with a therapeutically inert carrier material and, if desired, one or more other therapeutically active substances.
Claim 10
Dependent Claim 43 words
The use of a compound according to any one of claims 1 to 8 for the manufacture of a medicament against inflamma-tory, immunological, oncological, bronchopulmonary, dermato-logical or cardiovascular disorders or against asthma, AIDS or diabetic complications or for the stimulation of hair growth.
Claim 11
Dependent Claim 73 words
Compounds of the general formula wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , m, n, p and q have the significance given in claim 1 and X' represents -N(R 9' )- or -CHN(R 10' ,R 11' )- in which R 9' , R 10' and R 11' each represent hydrogen, alkyl, aralkyl, alkanoyl, alkoxycarbonyl or aryloxycarbonyl.

References Cited (Backward Citations)

EP0328026A1 Cited
EP0384349A1 Cited
EP0397060A2 Cited

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