KR890013002A - Substituted pyrroles - Google Patents

Abstract

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Description

Substituted pyrroles

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Claims (16)

A pharmaceutically acceptable salt with the following pyrrole of general formula (I) and the base of the acidic compound of general formula (I), and a pharmaceutically acceptable salt with the acid of the basic compound of general formula (I). Wherein R ¹ is hydrogen, alkyl, aryl, aralkyl, alkoxyalkyl, hydroxyalkyl, haloalkyl, aminoalkyl, monoalkylaminoalkyl, dialkylaminoalkyl, trialkylaminoalkyl, aminoalkylaminoalkyl, azido Alkyl, acylaminoalkyl, acylthioalkyl, alkylsulfonylaminoalkyl, arylsulfonylaminoalkyl, mercaptoalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylsulfonyloxyalkyl, alkylcarbonyloxy Alkyl, cyanoalkyl, amidinoalkyl, isothiocyanatoalkyl, glucopyranosyl, carboxyalkyl, alkoxycarbonylalkyl, aminocarbonylalkyl, hydroxyalkylthioalkyl, mercaptoalkylthioalkyl, arylthioalkyl or Carboxyalkylthioalkyl or the following general formula (a), (b), (c) or (d) group [Wherein, Het is a heterocyclyl group, W is NH, S or one bond, T is NH or S and V is O, S, NH, NNO ₂ , NCN or CHNO ₂ and Z is alkylthio , Amino, monoalkylamino or dialkylamino, Im is 1-imidazolyl, Ar is aryl and n is 2 to 6; R ² is hydrogen, alkyl, aralkyl, alkoxyalkyl, hydroxyalkyl, haloalkyl, aminoalkyl, monoalkylaminoalkyl, dialkylaminoalkyl, acylaminoalkyl, alkylsulfonylaminoalkyl, allylsulfonylaminoalkyl, mer Captoalkyl, alkylnioalkyl, carboxyalkyl, alkoxycarbonylalkyl, aminocarbonylalkyl, alkylthio or alkylsulfinyl; R ³ is a carbocyclic or heterocyclic aromatic group; R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently hydrogen, halogen, alkyl, hydroxy, alkoxy, aryloxy, haloalkyl, nitro, amino, acylamino, monoalkylamino, diarachylamino, alkylthio, Alkylsulfinyl or alkylsulfonyl; One of X and Y is O and the other is O, S, (H, OH) or (H, H); Provided that R ² is hydrogen, R ³ is 3-indolyl or 6-hydroxy-3-indolyl, R ⁴ , R ⁵ and R ⁷ are each hydrogen, R ⁶ is hydrogen or hydroxy and X and Y When are both O and R ² is hydrogen, R ³ is 3-indolyl, R ⁴ , R ⁵ and R ⁶ and R ⁷ are each hydrogen, X is (H, H) and Y is O, ¹ has a different group from hydrogen. The compound of claim 1, wherein R ¹ is hydrogen, alkyl, aralkyl, alkoxyalkyl, hydroxyalkyl haloalkyl, aminoalkyl, monoalkylaminoalkyl, dialkylaminoalkyl, azidoalkyl, acylaminoalkyl, alkylsulfonylamino Alkyl, arylsulfonylaminoalkyl, mercaptoalkyl, alkylthioalkyl, glucopyranosyl, carboxyalkyl, alkoxycarbonylalkyl, aminocarbonylalkyl, hydroxyalkylthioalkyl, mercaptoalkylthioalkyl, arylthioalkyl or carboxy Alkylthioalkyl. The compound of claim 2, wherein R ¹ is alkyl or aminoalkyl. The compound of claim 1, wherein R ¹ is isothiocyanatoalkyl, or a group of formula (b) wherein T is S and V is NH, Z is amino, or T is NH and V is NH or NNO ^- and Z is amino. The compound of any one of claims 1-4, wherein R ² is hydrogen. 6. The compound of claim 1, wherein R ³ is phenyl monosubstituted with halogen, alkyl, alkoxy, haloalkyl, nitro, amino, alkylthio, alkylsulfinyl or alkylsulfonyl. The compound of any one of claims 1-5, wherein R ³ is a group of formula (VII). Wherein R ^{1 ′} , R ^{2 ′} , R ^{5 ′} , R ^{6 ′} and R ^{7 ′} are as defined for R ¹ , R ² , R ⁴ , R ⁵ , R ⁶ and R ⁷ in claim 1. 8. The compound of claim 1, wherein R ⁴ , R ⁵ , R ⁶ and R ⁷ are each hydrogen. 9. The compound of claim ¹ , wherein R ¹ is methyl, 3-aminopropyl, 3-isothiocyanatopropyl or a group of formula (b), wherein T is S and V is NH , Z is amino and n is 3 or T is NH, V is NH or NNO ₂ , Z is amino and n is 3], R ² is hydrogen, R ³ is chlorine, bromine, methyl, Methoxy, trifluoromethyl, nitro, amino, methylsulfinyl or methylsulfonyl or a group of formula ^{IV in} claim ⁵ wherein R ¹ ′ is methyl and R ² ′, R ⁴ ′ , R ⁵ ′, R ⁶ ′ and R ⁷ ′ are each monosubstituted phenyl, and R ⁴ , R ⁵ , R ⁶ and R ⁷ are each hydrogen. Pyrrole consisting of the following compounds; 3- (2-chlorophenyl) -4- (1-methyl-3-indolyl) -1H-pyrrole-2,5-dione, 3- (2-nitrophenyl) -4- (1-methyl-3- Indolyl) -1H-pyrrole-2,5-dione, 3,4-bis (1-methyl-3-yldolyl) -1H-pyrrole-2,5-dione, 3- [1- (3-aminopropyl ) -3-indolyl) -4- (1-methyl-3-indolyl] -1H-pyrrole-2,5-dione, 1- [1- [3- (amidinothio) propyl-3-indoleyl ] -4- (1-methyl-3-indolyl) -1H-pyrrole-2,5-dione, 3- (1-methyl-3-indolyl) -4- [1-3- (2-nitrogu Anidino-propyl] -3-indolyl) -1H-pyrrole-2,5-dione, and 3- [1- (3-isothiocyanatopropyl) -3-indolyl) -4- (1- Methyl-3-indolyl) -1H-pyrrole-2,5-dione. The compound according to claim 1, for use as a therapeutically active substance, in particular as an anti-inflammatory, immunological, bronchial and cardiovascular active substance. (a) reacting a compound of formula (II) with ammonia under pressure or hexamethyldisilazane and methanol to produce a compound of formula (I) wherein X and Y are both O; or (b) Reacting a compound of III) with a compound of formula IV to prepare a compound of formula I wherein R ¹ is hydrogen and X and Y are both O, or (c) a compound of formula Reacting with an alkali metal derivative of benzimidazole to prepare a compound of formula (I) wherein R ³ is 1-benzimidazolyl and X and Y are both O, or (d) a formula of which both X and Y are 0 Reacting a compound of (I) with a sulfiding agent to produce a compound of formula (I) wherein one of X and Y is O and the other is S, or (e) general formula (I) wherein X and Y are both O Is reduced to a metal hydride complex to produce a compound of formula (I) wherein one of X and Y is O and the other is (H, OH), or (f) Catalytically hydrogenating a compound of formula (I), the other of which is (H, OH), to prepare a compound of formula (I), wherein one of X and Y is O and the other is (H, H), or Or (g) appropriately N-substituting a compound of formula (I) wherein R ¹ is hydrogen to prepare a compound of formula (I) wherein R ¹ is alkyl, aralkyl, alkoxyalkyl or hydroxyalkyl, and (h ) Optionally, reactively modify the reactive substituents present in the compound of general formula (I) obtained, and (i) optionally also remove the acidic compound of general formula (I) with a pharmaceutically acceptable base. A process for preparing a compound according to any one of claims 1 to 10, characterized in that it is converted to a salt or a basic compound of formula (I) to a pharmaceutically acceptable salt with an acid. Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are as defined in claim 1, Hal is halogen and R ⁸ is as defined in claim 1 as R ³ . Or bromine. A medicament, in particular an anti-inflammatory, immunological, bronchial or cardiovascular agent, containing the compound according to any one of claims 1 to 10 and a therapeutically inert carrier material. Use of a compound according to any one of claims 1 to 10 for the manufacture of a medicament for inflammatory, immunological, bronchial lung or cardiovascular disease. The compound according to any one of claims 1 to 10, prepared by the method of claim 12 or by a method that is clearly chemically equivalent thereto. The compounds, medicaments and uses described herein, in particular with reference to Examples. ※ Note: The disclosure is based on the initial application.