- Male oral contraceptive N-alkylimidazole derivatives, compositions, and method of use therefor
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A compound useful as antifungal, antibacterial and antiprotozoal agents and as spermicides have the formula STR1 and the acid addition salts thereof wherein Z is oxygen or sulfur; m is 0, 1, 2 or 3; n is 1, 2 or 3; R1 is hydrogen; alkyl; cycloalkyl; cycloalkyl-lower-alkyl; optionally substituted phenyl; phenyl-lower-alkyl; monocyclic heteroaromatic ring; monocyclic heteroaromatic-lower-alkyl; naphthyl; or naphthyl-lower-alkyl. A and B are independently hydrogen, halo, lower alkyl or lower alkoxy and either one of A or B may be nitro, amino or alkanoylamino; Q is (a) NR2 R3 or (b) NR4 C(X)YR5 wherein X is oxygen or sulfur; Y is oxygen, sulfur, NR6 or a bond; R2 is hydrogen; alkyl; cycloalkyl; cycloalkyl-lower-alkyl; optionally substituted phenyl or optionally substituted phenyl-lower-alkyl; R3 is hydrogen or lower alkyl; or R2 and R3 together with N is a five or six membered optionally substituted ring; R4 and R6 are independently hydrogen or lower alkyl; R5 is lower alkyl; cycloalkyl; phenyl; or optionally substituted phenyl or phenyl-lower-alkyl.
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- β-Adrenergic blocking agents: Substituted phenylalkanolamines. Effect of side-chain length on β-blocking potency in vitro
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The synthesis of a group of potential β-blockers bearing a new 5-ethoxysalicylamide substituent on nitrogen is described. These compounds were tested for β-adrenergic blocking potency in vitro and compared with analogous compounds bearing a tert-butyl group on nitrogen. The new N-substituent increased the β-blocking potency substantially. In a series of five homologous compounds of the type Ar(CH2)(n)CHOHCH2NHR (R = 5-ethoxysalicylamide; n = 0-4), two maxima of β-blocking potency were found for n = 0 and 2. Moreover, the carbon isostere of the corresponding (aryloxy)propanolamine still proved to be a very potent β-blocker. The ether oxygen in the side chain is therefore not an absolute requirement for activity. Structure-activity relationships are discussed.
- Fuhrer,Ostermayer,Zimmermann,Meier,Mueller
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p. 831 - 836
(2007/10/02)
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- Derivatives of thienyl- and furyl-substituted N-butyl and N-phenyl imidazoles
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The compounds of the present invention are represented by the formula STR1 wherein R1 and R2 are the same or different and are optionally substituted furyl or thienyl the substituents independently selected from the group halo, C1 to C6 alkyl and C1 to C6 alkoxy or optionally substituted phenyl the substituents independently selected from the group halo, C1 to C4 alkyl, C1 to C4 alkoxy and trifluoromethyl; X is oxygen or sulfur; m is the integer 0; and n is the integer 2 or 3; and the antimicrobial acid addition salts thereof, with the proviso that when either R1 or R2 is said optionally substituted phenyl the other R1 or R2 is said optionally substituted furyl or thienyl. The compounds are useful for combatting fungi, bacteria and protozoa. They also have spermatocidal and spermatostatic activity.
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- Derivatives of substituted N-alkyl imidazoles and compositions and methods containing the same
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Compounds of the formula STR1 wherein R1 is phenethyl and R2 is phenyl, each of said phenethyl or phenyl independently being unsubstituted or substituted in the phenyl ring by from 1 to 3 substituents selected from the group consisting of halo, lower alkyl and lower alkoxy with the proviso that at least one of R1 and R2 be substituted by lower alkoxy; X is oxygen or sulfur; and the antimicrobial acid addition salts thereof are useful as antifungal, antibacterial and antiprotozoal agents.
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