Compounds of formula (I):

##STR00001##

where R.sup.1, R.sup.2, R.sup.3, R.sup.4a, R.sup.4b, R.sup.5, R.sup.6 and R.sup.7 are defined herein, or stereoisomers or pharmaceutically acceptable salts thereof, are described herein. Such compounds have activity as SHIP1 modulators, and thus may be used to treat any of a variety of diseases, disorders or conditions that would benefit from SHIP1 modulation. Compositions comprising a compound of formula (I) in combination with a pharmaceutically acceptable carrier or diluent are also disclosed, as are methods of SHIP1 modulation by administration of such compounds to an animal in need thereof.

Compounds of formula (I):

##STR00001##

where R.sup.1, R.sup.2, R.sup.3, R.sup.4a, R.sup.4b, R.sup.5, R.sup.6 and R.sup.7 are defined herein, or stereoisomers or pharmaceutically acceptable salts thereof, are described herein. Such compounds have activity as SHIP1 modulators, and thus may be used to treat any of a variety of diseases, disorders or conditions that would benefit from SHIP1 modulation. Compositions comprising a compound of formula (I) in combination with a pharmaceutically acceptable carrier or diluent are also disclosed, as are methods of SHIP1 modulation by administration of such compounds to an animal in need thereof.

Provided is a method of purifying a terpenoid amino alcohol derivative, including providing a crude terpenoid amino alcohol derivative; performing an acid/base crystallization process of the crude terpenoid amino alcohol derivative to obtain an organic salt; and reacting the organic salt with NaOH and toluene to obtain a purified terpenoid amino alcohol derivative. Also provided is a method of preparing p-mentha-2,8-diene-1-ol from the purified terpenoid amino alcohol derivative.

Provided is a method of purifying a terpenoid amino alcohol derivative, including providing a crude terpenoid amino alcohol derivative; performing an acid/base crystallization process of the crude terpenoid amino alcohol derivative to obtain an organic salt; and reacting the organic salt with NaOH and toluene to obtain a purified terpenoid amino alcohol derivative. Also provided is a method of preparing p-mentha-2,8-diene-1-ol from the purified terpenoid amino alcohol derivative.

The present invention is directed to .sup.13C and/or .sup.2H isotope enhanced ambroxol (“isotope enhanced ambroxol”) and its use in the treatment of autophagy infections, especially mycobacterial and other infections, disease states and/or conditions of the lung, such as tuberculosis, especially including drug resistant and multiple drug resistant tuberculosis. Pharmaceutical compositions comprising isotope enhanced ambroxol, alone or in combination with an additional bioactive agent are useful against an autophagy mediated disease state and/or condition, for example, a Mycobacterium infection, Chronic Obstructive Pulmonary Disease (COPD), asthma, pulmonary fibrosis, cystic fibrosis, Sjogren's disease and lung cancer. Methods of treating autophagy disease states and/or conditions, especially including autophagy disease states or conditions which occur principally in the lungs of a patient represent a further embodiment of the present invention. Methods of synthesizing compounds according to the present invention are disclosed herein.

The present invention is directed to .sup.13C and/or .sup.2H isotope enhanced ambroxol (“isotope enhanced ambroxol”) and its use in the treatment of autophagy infections, especially mycobacterial and other infections, disease states and/or conditions of the lung, such as tuberculosis, especially including drug resistant and multiple drug resistant tuberculosis. Pharmaceutical compositions comprising isotope enhanced ambroxol, alone or in combination with an additional bioactive agent are useful against an autophagy mediated disease state and/or condition, for example, a Mycobacterium infection, Chronic Obstructive Pulmonary Disease (COPD), asthma, pulmonary fibrosis, cystic fibrosis, Sjogren's disease and lung cancer. Methods of treating autophagy disease states and/or conditions, especially including autophagy disease states or conditions which occur principally in the lungs of a patient represent a further embodiment of the present invention. Methods of synthesizing compounds according to the present invention are disclosed herein.

A process for producing a compound of the formula (T)

##STR00001##

involves at least reacting a compound of the formula (U)

##STR00002##

with hydrogen and water in the presence of at least one homogeneous transition metal catalyst TMC 1.

A process for producing a compound of the formula (T)

##STR00001##

involves at least reacting a compound of the formula (U)

##STR00002##

with hydrogen and water in the presence of at least one homogeneous transition metal catalyst TMC 1.

A process for producing a compound of the formula (I)

##STR00001##

involves at least reacting a compound of the formula (II)

##STR00002##

with hydrogen and water in the presence of at least one homogeneous transition metal catalyst TMC 1.

A process for producing a compound of the formula (I)

##STR00001##

involves at least reacting a compound of the formula (II)

##STR00002##

with hydrogen and water in the presence of at least one homogeneous transition metal catalyst TMC 1.