Diamine compounds

Claim 1

A process for preparing a compound of the formula I wherein R¹ represents a C₆₋₁₀ aryl group optionally substituted by one, two or three substituents independently selected from halogen, hydroxy, trifluoromethyl, cyano, nitro, amino, aminocarbonyl, carboxy, sulphonic acid, (C₁₋₆ alkoxy)carbonyl, C₁₋₆ alkyl sulphide, C₁₋₆ alkyl sulphoxide, C₁₋₆ alkyl sulphone, C₁₋₆ alkanoyl, C₁₋₆ alkoxy, C₃₋₆ alkenyloxy, C₃₋₆ alkynyloxy, C₁₋₆ acylamino, C₁₋₆ acylmethylamino, C₁₋₆ alkyl, C₁₋₆ monoalkylamino, (C₁₋₆ monoalkylamino)carbonyl, and a group of formula II in which A is -CO- or a single bond and R⁶ and R⁷ which may be the same or different each represent a C₁₋₆ alkyl group or R⁶ and R⁷ together with the intervening nitrogen atom represents a cyclic amine with 4 to 7 ring atoms and where appropriate the oxides thereof), or R¹ represents a heterocyclic moiety comprising a 5-or 6- membered heterocyclic ring containing one or two heteroatoms independently selected from oxygen, nitrogen and sulphur, the ring optionally being fused with a benzene ring and the heterocyclic and/or benzene ring being optionally substituted on carbon by one or more substituents selected from amino, halogen, hydroxy (and keto-tautomers thereof) C₁₋₆ alkyl, C₁₋₆ alkoxy, C₃₋₆ alkenyloxy and C₃₋₆ alkynyloxy any nitrogen heteroatom optionally carrying an oxygen atom or a hydroxy or C₁₋₃ alkyl group; X represents a single bond, -CH₂-, -OCH₂-, -SCH₂-, -SOCH₂-, -SO₂CH₂- or -CH₂-CH₂-; R² represents hydrogen or C₁₋₃ alkyl; R³ represents an alkyl, cycloalkyl or cycloalkylmethyl group having up to 7 carbon atoms, the cycloalkyl moiety where present, having 3 to 6 carbon atoms, said group optionally being substituted by one or more substituents selected from hydroxy, amino, amidino, guanidino, aminocarbonyl, carboxy, C₁₋₆ alkoxy, (C₁₋₆ alkoxy)carbonyl, (C₃₋₆ alkenyloxy)carbonyl, (C₃₋₆ alkynyloxy)carbonyl, C₁₋₆ alkanoyloxy, C₁₋₆ alkylsulphide, C₁₋₆ alkylsulphoxide, C₁₋₆ alkylsulphone, C₁₋₆ (monoalkylamino)carbonyl, C₁₋₆ acylamino, C₁₋₆ acylmethylamino, C₁₋₆ monoalkylamino, a group of formula II (as herein defined); or R³ represents the group -B-R¹ a in which B represents -CH₂-, -CH(CH₃)- or a single bond and R¹ a represents an optionally substituted C₆₋₁₀ carbocyclic aryl group as defined for R¹; or R³ represents the group -D-R b in which D represents a single bond, -CH 2- , -CH(CH₃)-, -CH₂-O-, -CH(CH₃)-O-, -CH₂-S-, -CH(CH₃)-S-, -CH₂-NH- or -CH(CH₃)-NH- and R b represents a 4-to 6-membered heterocyclic ring containing up to 4 heteroatoms selected from oxygen, sulphur and nitrogen, the heterocyclic ring optionally being substituted on nitrogen or sulphur by oxygen or on nitrogen by hydroxy or C₁₋₃ alkyl and/or the ring optionally being substituted on carbon by one or more substituents selected from amino, hydroxy, thio (and their tautomers), cyano, halogen, C₁₋₃ alkoxy, C₁₋₃ monoalkylamino, C₁₋₃ acylamino, C₁₋₃ acylmethylamino, C₁₋₃ alkylthio and the group of formula II as herein defined; and R⁴ and R⁵, which may be the same or different, each represents a C₃₋₅ alkenyl, C₃₋₅ alkynyl, C₁₋₆ alkyl, or C₄₋₇ cycloalkylalkyl group; or R⁴ and R⁵ together with the intervening nitrogen atom represent a 4-7-membered heterocyclic ring which optionally contains a further heteroatom selected from oxygen and sulphur] or a racemate thereof, and the salts of said compound or racemate, which comprises:- a) reacting a compound of the formula IV R¹-X-Y (in which R¹ and X are as hereinbefore defined and Y represents an acid or an activated derivative thereof), with a compound of formula V (in which R², R³, R⁴ and R⁵ are as hereinbefore defined) or a racemate thereof, optionally in protected form, and where necessary deprotecting the compound thus obtained to form a compound of formula I or racemate thereof b) for the preparation of a compound of formula I in which R² is hydrogen, selectively reducing a compound of formula III, wherein R¹,R³,R⁴,R⁵ and X are as hereinbefore defined, or a racemate thereof optionally in protected form and where neccesary deprotecting the compound thus obtained to form a compound of formula I or racemate thereof c) for the preparation of a compound of formula I in which R³ represents a moiety containing one or more free hydroxy groups or a free amino group, hydrolysing a corresponding compound in which R³ represents a moiety containing one or more acyloxy or alkoxy groups or an acylamino group. d) for the preparation of a compound of formula I in which R³ represents a moiety which contains the C₁₋₆ alkanoyloxy group, the selective C₁₋₆ alkanoylation of a corresponding compound of the present invention in which R³ represents a moiety which contains a hydroxy group e) for the preparation of a compound of formula I in which X, R¹ and/or R³ contains a -SO₂-moiety, oxidising a corresponding compound of the present invention in which X, R¹ and/or R³ contains an -S- or -SO₂-moiety f) for the preparation of a compound of formula I in which X, R¹ and/or R³ contains a -SO- moiety, oxidising a corresponding compound of the present invention in which X, R¹ and/or R³ contains an -S- moiety g) for the preparation of a compound of formula I in which R¹ and/or R³ contains a C₁₋₆ alkoxy, C₃₋₆ alkenyloxy or C₃₋₆ alkynyloxy group, alkylating, alkenylating or alkynylating a corresponding compound of the present invention in which R¹ and/or R³ contains a hydroxy group h) for the preparation of a compound of formula I in which R¹ and/or R³ represents a moiety containing an acylamino group, acylating a corresponding compound of the present invention in which R¹ and/or R³ represent a moiety containing an amine group and, whereafter, when the compound of formula I or a racemate thereof is obtained in the form of a base and a salt is required, reacting said compound of formula I obtained with an acid to form the salt.