Patent classifications
C07J9/00
OXYSTEROLS AND METHODS OF USE THEREOF
Compounds are provided according to Formula (I):
##STR00001##
and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein R.sup.2, R.sup.3, R.sup.4, R.sup.5, and R.sup.6 are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.
PROCESS FOR ISOLATION OF STEROLS AND A FRACTION RICH IN FATTY ACIDS AND RESIN ACIDS
The invention relates to a process for recovering sterols and a fraction rich in fatty acids and resin acids from tall oil pitch, said process comprising a) saponifying the tall oil pitch with an alkali to hydrolyse esters included in the pitch to free alcohols and organic acids in salt form, b) acidulating the saponified pitch with a mineral acid to convert the organic acids in salt form into free organic acids and to form an organic phase and an aqueous phase; wherein mineral acid is provided in an amount to produce an aqueous phase with a pH value of at most 3.8, c) separating the aqueous phase with a pH value of at most 3.8 from the organic phase, d) evaporation fractionating the organic phase in a thin film evaporator to obtain a distillate rich in fatty acids and resin acids and a bottom fraction rich in sterols, e) evaporation fractionating the bottom fraction to obtain a distillate rich in sterols, and f) subjecting the sterols in the sterol-rich distillate to crystallisation purification, wherein the process excludes a step of adding alkali between step c) and step d).
PROCESS FOR ISOLATION OF STEROLS AND A FRACTION RICH IN FATTY ACIDS AND RESIN ACIDS
The invention relates to a process for recovering sterols and a fraction rich in fatty acids and resin acids from tall oil pitch, said process comprising a) saponifying the tall oil pitch with an alkali to hydrolyse esters included in the pitch to free alcohols and organic acids in salt form, b) acidulating the saponified pitch with a mineral acid to convert the organic acids in salt form into free organic acids and to form an organic phase and an aqueous phase; wherein mineral acid is provided in an amount to produce an aqueous phase with a pH value of at most 3.8, c) separating the aqueous phase with a pH value of at most 3.8 from the organic phase, d) evaporation fractionating the organic phase in a thin film evaporator to obtain a distillate rich in fatty acids and resin acids and a bottom fraction rich in sterols, e) evaporation fractionating the bottom fraction to obtain a distillate rich in sterols, and f) subjecting the sterols in the sterol-rich distillate to crystallisation purification, wherein the process excludes a step of adding alkali between step c) and step d).
PRODUCTION METHOD OF TELOMERASE ACTIVATORS AND TELOMERASE ACTIVATORS OBTAINED BY THIS METHOD
A method for producing telomerase activators which provide to obtain new/novel molecules (metabolites) from saponin group compounds by using biotransformation with endophytic fungi and telomerase activators obtained by this method. Included is the elucidation of chemical structures and investigation of the effects of telomerase enzyme activation in cells. These molecules have the potential to be used in diseases and/or conditions that can be treated/ameliorated by telomerase activation and associated with telomere shortening (For example; HIV, degenerative diseases, acute and chronic wound healing, ex vivo cell therapies and stem cell proliferation due to increment in vitro and ex-vivo replicative capacity of cells).
NOVEL METHOD FOR SYNTHESIZING 25-OH CHOLESTEROL/CALCIFEDIOL FROM PHYTOSTEROL
The present invention discloses novel method for synthesizing vegan 25-OH cholesterol/Calcifediol from inexpensive crude phytosterol. According to the method, Phytosterols are reacted to form corresponding i-steroid through tosylation and methanolysis. i-steroid on reductive ozonolysis to C-22 alcohol and conversion via C-22 tosylate to C-22 iodide in good yield. Coupling of C-22 tosylate with Grignard reagent of 4-bromo-2-methyl-2-[(trimethylsilyl)oxy]butane followed by deprotection yielded 25-OH cholesterol. In a process variant, nickel mediated conjugate addition of C-22 iodide to an electron deficient alkene ethyl acrylate and treating corresponding ester with methyl magnesium bromide as means of installing the side chain of 25-OH cholesterol in high yield. Further bromination reaction of 25-OH cholesterol diacetate followed by dehydrobromination using TBAF yielded 25-OH 7-dehydrocholesterol. Further photo reaction of 25-OH 7-dehydrocholesterol in to previtamin D3 using high or medium pressure mercury lamp and subsequent thermal reaction of previtamin D3 to 25-OH vitamin D3 (Calcifediol) in good yield.
NOVEL METHOD FOR SYNTHESIZING 25-OH CHOLESTEROL/CALCIFEDIOL FROM PHYTOSTEROL
The present invention discloses novel method for synthesizing vegan 25-OH cholesterol/Calcifediol from inexpensive crude phytosterol. According to the method, Phytosterols are reacted to form corresponding i-steroid through tosylation and methanolysis. i-steroid on reductive ozonolysis to C-22 alcohol and conversion via C-22 tosylate to C-22 iodide in good yield. Coupling of C-22 tosylate with Grignard reagent of 4-bromo-2-methyl-2-[(trimethylsilyl)oxy]butane followed by deprotection yielded 25-OH cholesterol. In a process variant, nickel mediated conjugate addition of C-22 iodide to an electron deficient alkene ethyl acrylate and treating corresponding ester with methyl magnesium bromide as means of installing the side chain of 25-OH cholesterol in high yield. Further bromination reaction of 25-OH cholesterol diacetate followed by dehydrobromination using TBAF yielded 25-OH 7-dehydrocholesterol. Further photo reaction of 25-OH 7-dehydrocholesterol in to previtamin D3 using high or medium pressure mercury lamp and subsequent thermal reaction of previtamin D3 to 25-OH vitamin D3 (Calcifediol) in good yield.
SMALL MOLECULE MODULATORS OF GUT BACTERIAL BILE ACID METABOLISM
Described herein are methods and compositions related to inhibiting bile salt hydrolase (BSH) and uses thereof. Provided herein is a method for treating a metabolic disorder (e.g., diabetes, obesity), gastrointestinal disease (e.g., a gastrointestinal infection; inflammatory bowel disease (IBD); appendicitis; Crohn's disease (CD); ulcerative colitis (UC); gastritis; enteritis; esophagitis; pancreatitis; diabetes; hepatitis; liver diseases (e.g., Non-alcoholic Fatty Liver Disease (NAFLD); non-alcoholic steatohepatitis (NASH); hepatitis A; hepatitis B; hepatitis C; autoimmune hepatitis; and cirrhosis of the liver) gastroesophageal reflux disease (GERD); celiac disease; diverticulitis; food intolerance; ulcer; infectious colitis; irritable bowel syndrome; leaky gut; and cancer), cancer (e.g., cancer of the digestive system, liver cancer), or an inflammatory disease (e.g., Crohn's disease, inflammatory bowel disease, ulcerative colitis, pancreatitis, hepatitis, appendicitis, gastritis, diverticulitis, celiac disease, food intolerance, enteritis, ulcer, gastroesophageal reflux disease (GERD), psoriatic arthritis, psoriasis, and rheumatoid arthritis) in a subject in need thereof comprising administering to a subject a compound of Formulae (I)-(XVIII).
Process for isolation of sterols and a fraction rich in fatty acids and resin acids
The invention relates to a process for recovering sterols and a fraction rich in fatty acids and resin acids from tall oil pitch, said process comprising a) saponifying the tall oil pitch with an alkali to hydrolyse esters included in the pitch to free alcohols and organic acids in salt form, b) acidulating the saponified pitch with a mineral acid to convert the organic acids in salt form into free organic acids and to form an organic phase and an aqueous phase; wherein mineral acid is provided in an amount to produce an aqueous phase with a pH value of at most 3.8, c) separating the aqueous phase with a pH value of at most 3.8 from the organic phase, d) evaporation fractionating the organic phase in a thin film evaporator to obtain a distillate rich in fatty acids and resin acids and a bottom fraction rich in sterols, e) evaporation fractionating the bottom fraction to obtain a distillate rich in sterols, and f) subjecting the sterols in the sterol-rich distillate to crystallisation purification, wherein the process excludes a step of adding alkali between step c) and step d).
Process for isolation of sterols and a fraction rich in fatty acids and resin acids
The invention relates to a process for recovering sterols and a fraction rich in fatty acids and resin acids from tall oil pitch, said process comprising a) saponifying the tall oil pitch with an alkali to hydrolyse esters included in the pitch to free alcohols and organic acids in salt form, b) acidulating the saponified pitch with a mineral acid to convert the organic acids in salt form into free organic acids and to form an organic phase and an aqueous phase; wherein mineral acid is provided in an amount to produce an aqueous phase with a pH value of at most 3.8, c) separating the aqueous phase with a pH value of at most 3.8 from the organic phase, d) evaporation fractionating the organic phase in a thin film evaporator to obtain a distillate rich in fatty acids and resin acids and a bottom fraction rich in sterols, e) evaporation fractionating the bottom fraction to obtain a distillate rich in sterols, and f) subjecting the sterols in the sterol-rich distillate to crystallisation purification, wherein the process excludes a step of adding alkali between step c) and step d).
(17-)-3-oxoandrost-4-en-17-yl dodecanoate compositions and methods of preparation and use
Disclosed are bioavailable solid state (17-β)-3-Oxoandrost-4-en-17-yl dodecanoate compositions and methods of use in administration to mammals in need of thereof. The (17-β)-3-Oxoandrost-4-en-17-yl dodecanoate is preferably provided in a solid state crystalline form having a plurality of peaks corresponding to the peaks shown in FIG. 2, a plurality of crystallites ranging in size from about 40 nm to about 60 nm based as identified via powder x-ray diffraction spectra, and a melting point in the range of about 51° C. to about 63° C. The compositions may be provided in oral or injectable administration form for the treatment of conditions such as in need of testosterone therapy. An exemplary chemical structure of a (17-β)-3-Oxoandrost-4-en-17-yl dodecanoate composition disclosed herein is as follows: ##STR00001##