213250-59-0

A method for producing highly pure p-toluic acid by a simple solid-liquid separation operation using as a raw material a substance inducible from a biomass resource and suitable for fermentation production by a microorganism is disclosed. The method for producing p-toluic acid includes: a dehydration reaction step of dehydrating Compound(s) (1)-(4), which are substances inducible from biomass resources and suitable for fermentation production by microorganisms; and a solid-liquid separation step of recovering a solid produced by this dehydration reaction by a simple solid-liquid separation operation.

Disclosed are 2-methylene analogs of vitamin D3 and related compounds, their biological activities, and various pharmaceutical uses for these analogs. Particularly disclosed are 1α-hydroxy-2-methylene-vitamin D3, (20S)-1α-hydroxy-2-m

In an attempt to prepare Vitamin D analogues that are superagonists, (20R)- and (20S)-isomers of 1α-hydroxy-2-methyleneVitamin D3 and 1α,25-dihydroxy-2-methyleneVitamin D3 have been synthesized. To prepare the desired A-ring dienyne

The synthesis of two new A-ring precursors, useful for the convergent assembly of 2α-ethyl and 2β-ethyl derivatives of 19-nor-1α,25- dihydroxyvitamin D3, is described. These building blocks were prepared in 14 steps from quinic acid, which led to a new and practical synthesis of 2α-ethyl-14-epi-19-nor-20-epi-23-yne-1,25(OH) 2D3, an analog that shows a remarkably low calcemic effect in mice, while retaining the ability to promote cell differentiation and to inhibit cell proliferation in a number of human cancer cell lines. Two new phosphanone building blocks, useful for the stereocontrolled synthesis of 2-ethyl-substituted 19-nor analogs of 1α,25-dihydroxyvitamin D 3, were prepared from quinic acid. This route offers an attractive practical solution for the introduction of these synthetically challenging but highly interesting A-ring modifications. Copyright

The present invention relates to the treatment of ostogenesis imperfecta by adminstering to a patient in need thereof a 2-alkylidene-19-nor-vitamin D derivative, optionally with a bisphosphonate. Particularly, the present invention relates to the treatmen

Methods for treating and preventing obesity, inhibiting adipocyte differentiation, inhibiting increased SCD-1 gene transcription, and/or reducing body fat in a subject include administering at least one analog of 1α,25-dihydroxyvitamin D3 or 1α

The present invention relates to methods of treating or preventing a second hip fracture, the methods comprising administering to a patient in need thereof a 2-alkylidene-19-nor-vitamin D derivative. Particularly, the present invention relates to methods

Various compounds such as those having the formula I and XIV where the variables have the values described herein antagonize the vitamin D receptor and are useful in treating conditions such as asthma and in preparing medicaments for use in antagonizing the vitamin D receptor or treating conditions such as asthma

The present invention relates to pharmaceutical compositions and methods of treatment comprising administering to a patient in need thereof a combination of a 2-alkylidene-19-nor-vitamin D derivative and an estrogen agonistlantagonist or a pharmaceuticall

The present invention relates to methods of treating osteopenia or male osteoporosis, the methods comprising administering to a patient in need thereof a 2-alkylidene-19-nor-vitamin D derivative. Particularly, the present invention relates to methods of t

The present invention relates to methods of treating osteosarcoma, the methods comprising administering to a patient in need thereof a 2-alkylidene-19-nor-vitamin D derivative. Particularly, the present invention relates to methods of treating osteosarcom

The present invention relates to methods of treating hypogonadism or andropause, the methods comprising administering to a patient in need thereof a 2-alkylidene-19-nor-vitamin D derivative. Particularly, the present invention relates to methods of treati

The present invention relates to methods of treating frailty, muscle damage or sarcopenia, the methods comprising administering to a patient in need thereof a 2-alkylidene-19-nor-vitamin D derivative. Particularly, the present invention relates to methods

The present invention relates to methods of enhancing peak bone mass in adolescence, the methods comprising administering to a patient in need thereof a 2-alkylidene-19-nor-vitamin D derivative. Particularly, the present invention relates to methods of en

The present invention relates to methods of treating anorexia or low bone mass in females exhibiting aggressive athletic behavior, the methods comprising administering to a patient in need thereof a 2-alkylidene-19-nor-vitamin D derivative. Particularly,

The present invention relates to pharmaceutical compositions and methods of treatment comprising administering to a patient in need thereof a combination of a 2-alkylidene-19-nor-vitamin D derivative and an estrogen, or a pharmaceutically acceptable salt

The present invention relates to pharmaceutical compositions and methods of treatment comprising administering to a patient in need thereof a combination of a 2-alkylidene-19-nor-vitamin D derivatives and a bone morphogenetic protein or active fragment or

The present invention relates to pharmaceutical compositions and methods of treatment comprising administering to a patient in need thereof a combination of a 2-alkylidene-19-nor-vitamin D derivative and parathyroid hormone or an active fragment or varian

The present invention relates to pharmaceutical compositions and methods of treatment comprising administering to a patient in need thereof a combination of a 2-alkylidene-19-nor-vitamin D derivative and a bisphosphonate. Particularly, the present invention relates to pharmaceutical compositions and methods of treatment comprising administering to a patient in need thereof 2-methylene-19-nor-20(S)-1α, 25-dihydroxyvitamin D3and a bisphosphonate.

The present invention relates to pharmaceutical compositions and methods of treatment comprising administering to a patient in need thereof a combination of a 2-alkylidene-19-nor-vitamin D derivative and a cyclooxgenase-2 inhibitor, or a pharmaceutically acceptable salt or prodrug thereof. Particularly, the present invention relates to pharmaceutical compositions and methods of treatment comprising administering to a patient in need thereof 2-methylene-19-nor-20(S)-10,25-dihydroxyvitamin D3 and a cyclooxgenase-2 inhibitor, or a pharmaceutically acceptable salt or prodrug thereof.

The present invention relates to pharmaceutical compositions and methods of treatment comprising administering to a patient in need thereof a combination of a 2-alkylidene-19-nor-vitamin D derivative and an EP2 or EP4 selective agonist or a pharmaceutically acceptable salt or prodrug thereof. Particularly, the present invention relates to pharmaceutical compositions and methods comprising administering to a patient in need thereof 2-methylene-19-nor-20(S)-1α,25-dihydroxyvitamin D3 and an EP2 or EP4 selective agonist or a pharmaceutically acceptable salt or prodrug thereof.

The present invention relates to pharmaceutical compositions and methods of treatment comprising administering to a patient in need thereof a combination of a 2-alkylidene-19-nor-vitamin D derivative and a growth hormone secretagogue or a pharmaceutically

The present invention relates to methods of treating osteopenia or male osteoporosis, the methods comprising administering to a patient in need thereof a 2- alkylidene-19-nor-vitamin D derivative. Particularly, the present invention relates to methods of

The present invention relates to methods of treating hypocalcemic tetany or hypoparathyroidism, the methods comprising administering to a patient in need thereof a 2-alkylidene-1 9-nor-vitamin D derivative. Particularly, the present invention relates to m

The present invention relates to pharmaceutical compositions and methods of treatment comprising administering to a patient in need thereof a combination of a 2-alkylidene-19-nor-vitamin D derivative and an aromatase inhibitor. Particularly, the present i

This invention provides a novel class of vitamin D related compounds, namely, the 2-alkylidene-19-nor-vitamin D derivatives, as well as a general method for their chemical synthesis. The compounds have the formula: where Y1and Y2, which may be the same or different, are each selected from the group consisting of hydrogen and a hydroxy-protecting group, R6and R8, which may be the same or different, are each selected from hydrogen, alkyl, hydroxyalkyl and fluoroalkyl, or when taken together represent the group —(CH2)x— where x is an integer from 2 to 5, and where the group R represents any of the typical side chains known for vitamin D type compounds. These 2-substituted compounds are characterized by relatively high intestinal calcium transport activity and relatively high bone calcium mobilization activity resulting in novel therapeutic agents for the treatment of diseases where bone formation is desired, particularly low bone turnover osteoporosis. These compounds also exhibit pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as anti-cancer agents and for the treatment of diseases such as psoriasis.

This invention provides a novel class of vitamin D related compounds, namely, 2-alkyl-19-nor-vitamin D derivatives, as well as a general method for their chemical synthesis. The compounds have the formula: where Y1and Y2, which may b

This invention provides a novel class of vitamin D related compounds, namely, the 2-alkyl-19-nor-vitamin D derivatives, as well as a general method for their chemical synthesis. The compounds have the formula: where Y1 and Y2, which may be the same or different, are each selected from the group consisting of hydrogen and a hydroxy-protecting group, R6 is selected from the group consisting of alkyl, hydroxyalkyl and fluoroalkyl, and where the group R represents any of the typical side chains known for vitamin D type compounds. These 2-substituted compounds, especially the 2 alpha -methyl and the 2 alpha -methyl-20S derivatives, are characterized by relatively low intestinal calcium transport activity and high bone calcium mobilization activity resulting in novel therapeutic agents for the treatment of diseases where bone formation is desired, particularly low bone turnover osteoporosis. These compounds also exhibit pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as anti-cancer agents and for the treatment of diseases such as psoriasis.

This invention provides a novel class of vitamin D related compounds, namely, the 2-alkyl-19-nor-vitamin D derivatives, as well as a general method for their chemical synthesis. The compounds have the formula: STR1 where Y1 and Y2, w

This invention provides a novel class of vitamin D related compounds, namely, the 2-alkylidene-19-nor-vitamin D derivatives, as well as a general method for their chemical synthesis. The compounds have the formula: STR1 where Y1 and Y2/su

New highly active isomers of the natural hormone 1alpha, 25-dihydroxyvitamin D3 possessing an exomethylene group at the 2-position were prepared in a convergent manner, starting with (-)-quinic acid and the corresponding (20R)- and (20S)-25-hydroxy Grundm