International Flavors & Fragrances Inc.

Hoechst Roussel Pharmaceuticals

Hoechst Marion Roussel

Salvatore M Brucato

Mark A Sprecker

Marie R Hanna

Robert P Belko

Charles E Beck

Lawrence L Martin

Joseph F Payack

Novel 4,5-dihydro-4-heteroaryl-3H-1,3-benzodiazepines, intermediates, processes for the preparation thereof, and methods for treating depression, inhibiting convulsions and treating anxiety utilizing compounds and compositions thereof are disclosed.

4-heteroaryl-1,3-benzodiazepines and

Described are alkyl-substituted tetra- or hexahydrobenzopyran derivatives defined according to one of the generic structures: ##STR1## wherein Z is a moiety in the alternative either ##STR2## wherein in the moiety having the structure: ##STR3## R' is methyl or ethyl and in the moiety having the structure: ##STR4## one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds; wherein R.sub.1 and R.sub.2 taken separately represent hydrogen or C.sub.1 -C.sub.3 lower alkyl (with the proviso that R.sub.1 and R.sub.2 are not both hydrogen) or R.sub.1 and R.sub.2 taken together complete a C.sub.5 or C.sub.6 cycloalkyl moiety; and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, hair preparations, cosmetic powders and perfumed polymers. Also described are synthesis processes for preparing such alkyl-substituted tetra- or hexahydrobenzopyran derivatives by means of reacting isopulegol or an isomer thereof with an acetal or ketal.

Process for preparing alkyl substituted tetra- or hexahydrobenzopyran

Alkyl-substituted tetra- or hexahydrobenzopyran derivatives,

Described are alkyl-substituted tetra- or hexahydrobenzopyran derivatives defined according to one of the generic structures: ##STR1## wherein Z is a moiety in the alternative either ##STR2## wherein in the moiety having the structure: ##STR3## R' is methyl or ethyl and in the moiety having the structure: ##STR4## one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds; wherein R.sub.1 and R.sub.2 taken separately represent hydrogen or C.sub.1 -C.sub.3 lower alkyl (with the proviso that R.sub.1 and R.sub.2 are not both hydrogen) or R.sub.1 and R.sub.2 taken together complete a C.sub.5 or C.sub.6 cycloalkyl moiety; and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, hair preparations, cosmetic powder and perfumed polymers. Also described are synthesis processes for preparing such alkyl-substituted tetra- or hexahydrobenzopyran derivatives by means of reacting isopulegol or an isomer thereof with an acetal or ketal.

Described are 2,4-disubstituted and 2,2,4-trisubstituted tetrahydropyranyl-4-ethers defined according to the generic structure: ##STR1## wherein R' represents methyl or ethyl; R.sub.1 and R.sub.2 taken alone are the same or different hydrogen, phenyl, C.sub.1 -C.sub.8 alkyl or C.sub.2 -C.sub.8 alkenyl (with the proviso that R.sub.1 and R.sub.2 are not both hydrogen) and R.sub.1 and R.sub.2 taken together represent C.sub.5 -C.sub.12 cycloalkyl or alkyl cycloalkyl, and reaction products containing said 2,4-disubstituted and 2,2,4-trisubstituted tetrahydropyranyl-4-ethers taken alone or taken further together in admixture with compounds defined according to the generic structure: ##STR2## wherein in the compounds defined according to the structure: ##STR3## one of the dashed lines in the moiety: ##STR4## represents a carbon-carbon double bond and each of the other dashed lines represent carbon-carbon single bonds; and R.sub.1 ' and R.sub.2 ' taken alone or taken together are defined in the same manner that R.sub.1 and R.sub.2 are defined, supra; and organoleptic uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to bleach compositions, solid or liquid anionic, cationic, nonionic or zwitterionic detergents, perfume polymers, fabric softener compositions, fabric softener articles, cosmetic powders and hair preparations.

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Carteret, NJ, United States of America

Salvatore M Brucato