KR920016400A - Benzyloxyphenyl derivatives - Google Patents

Abstract

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Description

Benzyloxyphenyl derivatives

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Claims (9)

The compound of formula (I) in free form or, if present, in salt form Wherein R ₁ , R ₂ and R ₃ are independently of each other hydrogen, hydroxy, alkoxy, acyloxy, halogen or benzyloxy, wherein two of the substituents in adjacent positions are also aliphatic with the carbon atom to which they are attached , May form a heteroaliphatic, aromatic or heteroaromatic ring, R ₁ ′ is hydrogen, or R ₁ and R ₁ ′ in adjacent positions form an aromatic ring with the carbon atom to which they are attached, R ₂ And R ₃ are as defined above; R ₄ and R ₄ ′ independently of one another are hydrogen, alkyl, alkenyl, cyano, carboxy, alkoxycarbonyl, —CONR ₇ R ₈ , wherein R ₇ and R ₈ Are independently of each other hydrogen, alkyl, phenyl, or benzyl, or together with the nitrogen atom to which they are attached form a 5- or 6-membered saturated ring) or optionally hydroxy-, alkoxy- or halogen-substituted Phenyl or Is one of R ₄ , and R ₄ ′ is hydrogen, and the other forms an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring with R ₃ and three carbon atoms separating them; R ₅ is hydroxy, acyloxy, alkoxy, benzyloxy, amino, acylamino, or general formula Wherein each substituent is as defined above. R ₆ is carboxy alcoholcarbonyl, benzyloxycarbonyl, phenoxycarbonyl, alkenyloxycarbonyl, -CONR ₇ R ₈ , wherein R ₇ and R ₈ are as defined above) or cyano; R ₉ are both hydrogen or together with the carbon atom to which they are attached form an aromatic ring; Provided that at least one of R ₁ , R ₂ and R ₃ is not hydrogen or chlorine. The compound of claim ₁ , wherein R ₁ , R ₂ and R ₃ are not halogen, and the benzyloxy moiety is R ₆ . or A compound of formula (I) in free form or, if present, in salt form, at the position. The compound of claim 1, wherein R ₁ is hydrogen or alkoxy having 1 to 4 carbon atoms, or methylenedioxy with R _2, and R ₁ ′ is hydrogen, or R ₁ and R ₁ ′ in adjacent positions are attached. Together with the carbon atom to form a phenyl ring; R ₂ is hydroxy, alkoxy or acetoxy having 1 to 4 carbon atoms, or methylenedioxy together with R ₁ ; R ₃ is hydrogen, hydroxy or alkoxy having 1 to 4 carbon atoms; R ₄ and R ₄ ′ are hydrogen; R ₅ is hydroxy, acetoxy, alkoxy having 1 to 4 carbon atoms, amino, acetylamino, 2,5-dimethoxybenzyloxy or 3-acetoxybenzyloxy; R ₆ is carboxy, alkoxycarbonyl, cyano or —CONR ₇ R ₈ having a total of 2 to 5 carbon atoms, wherein R ₇ and R ₈ are independently of each other hydrogen, alkyl or benzyl having 1 to 4 carbon atoms, or Forms a piperidino with the attached nitrogen atom) and R ₉ are both hydrogen or together with the carbon atom to which they are attached form a phenyl ring; Provided that at least one of R ₁ , R _2, and R ₃ is not hydrogen or in free form or, if present, in salt form. The compound of claim ₁ , wherein R ₁ , R ₂ , R _3, and R ₄ are as defined in claim 1; R ₁ ′ and R ₉ are hydrogen; R ₅ is hydroxy, benzyloxy, alkoxy or acyloxy R ₅ is as defined in claim 1 except for carboxy and cyano; Provided that at least one of R ₁ , R ₂ , and R ₃ is not hydrogen or in free form or, if present, in salt form. The compound of claim 1, which is 5- (2,5-dimethoxybenzyloxy) -2-hydroxybenzoic acid methyl ester. The compound of claim 1 further comprising: 5- (2,5-dimethoxybenzyloxy) -2-hydroxybenzoic acid methyl ester; or 5- (2,5-dimethoxybenzyloxy) -2-hydroxybenzoic acid; Or 5- (2,5-dimethoxybenzyloxy) -2-hydroxybenzoic acid amide; or 5- (2,5-dimethoxybenzyloxy) -2-hydroxybenzoanitrile; or 5- (2,5 Dimethoxybenzyloxy) -2-methoxybenzoic acid methyl ester; Or 5- (2,5-dimethoxybenzyloxy) -2-hydroxybenzoic acid methyl ester; or R ₁ , R ₁ ′, R ₄ , R ₄ ′ and two R ₉ are all H and R ₂ , R The position of the benzyloxy moiety relative to ₃ , R ₅ , R ₆ and R ₆ is a compound of formula (I): 5-OCH ₂ , OCH ₂ , OH, COOCH ₃ and 4,3-OCH ₃ , OCH ₃ , OH, COOCH ₃ and 5,3-OCH ₃ , OCH ₃ , OH, COOCH ₃ , and 4,5-OCH ₃ , OCH ₃ , OH, COOCH ₃ and 3,5-OCH ₃ , OCH ₃ , OH , COOCH ₃ and 6,5-OCH ₃ , OCH ₃ , NHCOCH ₃ , COOCH ₃ and 5,5-OCH ₃ , OCH ₃ , NH ₃ , COOCH ₃ and 5,3-OH, H ₃ , OH ₃ , COOCH ₃ And 5,5-OCH ₃ , OH ₃ , OH ₃ , COOCH ₃ and 5,5-OCH ₃ , OCH ₃ , OH ₃ , CONHCH ₂ C ₆ H ₅ and 5,5-OCH ₃ , OCH ₃ , OH, 1 -piperidyl-carbonyl and _{5,5-OCH 3, OCH 3,} OH, CONHCH 3 and _{5,5-OCH 3, OCH 3,} 2-5- di -OCH _3-benzyloxy, 5,3 COOCH ₃ and -OCOCH ₃ , H, 3-acetoxybenzyloxy, COOCH ₃ and 5, or 3-OCOCH ₂ , H, OH, COOCH ₃ and 5; Or R ₁ ′ R ₄ , R ₄ ′ and R ₉ are all H, R ₅ is OH, R ₆ is COOCH ₃ , the position of the benzyloxy residue relative to R ₆ is 5-position, R ₁ , R ₂ And a compound of formula (I) wherein R ₃ is as follows; 3,4-OCH ₃ O-, 3,4-OCH ₃ O- and H, or 4-OCH ₃ , 3-OCH ₃ and OCH ₃ ; Or R ₃ is OCH ₃ , R ₄ and R ₄ ′ are H, R ₅ is COOCH ₃ , the position of the benzyloxy residue relative to R ₆ is 5-position, R ₁ ′, R ₁ , R ₂ and Both R ₅ are each compound of formula (I): H, H, 5-OCH ₃ and but-1,3-diene-1,4-diyl, or 4,5- (but-1 A compound of formula (I) in free form or, where present, in salt form, which is, 3-diene-1,4-diyl, 3-OCH ₂ , H and H. Reacting a compound of the general formula (II) with a compound of the general formula (III) in protected form, if desired; if the resulting compound is in protected form, S) is suitably removed and / or the resulting compound of formula (I) is converted to another compound of formula (I); A process for the preparation of a compound of formula (I) according to claim 1 comprising recovering the compound in the free form or, if present, in the salt form. Wherein R ₁ , R ₁ ′, R ₂ , R ₃ , R ₄ , R ₄ ′, R ₅ , R ₆ , and R ₉ are as defined in claim 1, and X is a leaving group. 8. The method of claim 7, wherein the reaction is carried out in the presence of triphenylphosphine and azodicarboxylic acid alkyl ester. A pharmaceutical composition comprising the compound according to claim 1 in free form or, if present, in pharmaceutically acceptable salt form with at least one pharmaceutically acceptable carrier or diluent. ※ Note: This is to be disclosed by the original application.