38562-01-5

Usage

Uses

Used in Pharmaceutical Industry:
Prostaglandin F2a tris salt is used as an oxytocic and abortifacient agent for inducing luteolysis in cows, sows, and mares. It is administered as a single injection via intramuscular (im) or subcutaneous (sc) routes, with the recommended dosage rate being 25 mg for cows, 10 mg for sows, and 5 mg for mares. Due to its extremely short half-life of only a few minutes, it is rapidly absorbed from the injection site and almost completely cleared following one or two passages through the liver and/or lungs.
Used in Research and Development:
Prostaglandin F2a tris salt is used as a biological research tool for studying the roles and interactions of prostaglandins in various physiological processes. Its close relationship with Prostaglandin E2 (PGE2) makes it an important compound for understanding the biosynthesis and functions of primary prostaglandins, as well as the role of Phospholipase A2 (PLA2) in the biosynthesis of PGF2α.
Brand Name:
Prostin F2 Alpha (Pharmacia & Upjohn) is the brand name for Prostaglandin F2a tris salt, which is used in the pharmaceutical industry for its oxytocic and abortifacient properties.

Originator

Prostin F2A,Upjohn,UK,1972

Indications

Dinoprost tromethamine salt (Prostaglandin F2α tromethamine salt) is an orally active, potent prostaglandin F (PGF) receptor (FP receptor) agonist. Dinoprost tromethamine salt is a luteolytic hormone produced locally in the endometrial luminal epithelium and corpus luteum (CL). Dinoprost tromethamine salt plays a key role in the onset and progression of labour.

Manufacturing Process

A solution of tris(hydroxymethyl)aminomethane (1.645 grams) in 3.0 ml of water at 60°C is added with vigorous stirring to a solution of PGF2α, (5.00 grams) in 700 ml of acetonitrile which has just been ought to its boiling point. The vessel which contained the aqueous amine solution is rinsed with three 0.66 ml portions of water, each rinsing being added with vigorous stirring to the acetonitrile solution. The mixture is then cooled to 25°C by immersion of the vessel in cool water. At the cloud point, the vessel wall (glass) below the liquid surface is scratched vigorously with a glass rod. The mixture is then maintained at 25°C for 24 hours. The resulting crystals are collected by filtration under nitrogen, washed on the filter with 50 ml of acetonitrile, and then dried by passing nitrogen at 50°C through the filter cake for one hour. Drying is completed in an oven at 70°C for 8 hours to give 5.965 grams of the tris(hydroxymethyl)aminomethane salt of PGF2α in free flowing crystalline form; MP 100°-101°C.

Therapeutic Function

Smooth muscle stimulant

Biochem/physiol Actions

Prostaglandin F2α is induced by uterine-produced oxytocin and acts on the corpus luteum to cause luteolysis and inhibit progesterone production.

Safety Profile

Poison by intraperitoneal, subcutaneous, intravenous, and intramuscular routes. Moderately toxic by ingestion. Human reproductive effects by intervagmal route: terminates pregnancy, effects on fertility. Experimental teratogenic and reproductive effects. When heated to decomposition it emits toxic fumes of NOx. See also other prostaglandin entries.

InChI:InChI=1/C20H34O5.C4H11NO3/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25;5-4(1-6,2-7)3-8/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25);6-8H,1-3,5H2/b7-4+,13-12+;/t15-,16+,17+,18-,19+;/m0./s1

Upstream product

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• 60623-67-8 (-)-7α-Hydroxy-3-oxo-6β-<3-oxo-1(E)-octenyl>-cis-2-oxabicyclo<3.3.0>octane 
• 32233-40-2 (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 26054-67-1 (-)-7α-hydroxy-6β-(3α-hydroxy-1E-octenyl)-cis-2-oxabicyclo<3.3.0>octan-3-one 
• 551-11-1 dinoprost 
• 77-86-1 2-amino-2-hydroxymethyl-1,3-propanediol 
• 62961-72-2 Corey aldehyde 
• 142-62-1 hexanoic acid 
• 106-70-7 methyl hexanoate 
• 36969-89-8 dimethyl 2-oxoheptylphosphonate 
• 306768-62-7 (S)-3-((S)-2-(4,4-pentamethylene-3-(4-(3-(2-methylphenyl)ureido)benzyl)-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl)acetylamino)-3-(4-methoxyphenyl)propionic acid 
• 306768-56-9 (3S)-(3,4-dimethoxyphenyl)-3-[(2S)-{2,4-dioxo-1-[4-(3-phenylureido)benzyl]-1,3-diazaspiro[4.5]dec-3-yl}-4-methylpentanoylamino]propionic acid 
• 306768-54-7 (S)-3-((S)-2-(4,4-pentamethylene-3-(4-(3-phenylureido)benzyl)-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl)acetylamino)-3-(2,4-dimethoxyphenyl)propionic acid 
• 306768-52-5 (S)-3-((S)-2-(4,4-pentamethylene-3-(4-(3-phenylureido)benzyl)-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl)acetylamino)-3-(4-methoxyphenyl)propionic acid 

Relevant academic research and scientific papers

Of the trometamol prostaglandin F2 α synthesis method (by machine translation)

The invention discloses a of the trometamol prostaglandin F2 α synthesis method, as the compound (-) - Corey lactone diol as raw materials, through the oxidation reaction to obtain lactone aldehyde, lactone aldehydechain after the weidiWeidi Greecehuo Naer reaction with - the lower side of the splicing an olefin, the olefin double-carbonyl after reduction to obtain the alcohol, with puncture ylide - wittich reaction the upper side of the obtained prostaglandin F2 α, then the prostaglandin F2 α of the trometamol after crystallization by dissolving of the trometamol prostaglandin F2 α. The synthesis method, without noble metal catalyst, there is little side reaction, high yield, low cost, less pollution, is suitable for industrial production. (by machine translation)

Novel inhibitors of chymase

The present invention is directed to a compound of formula (I), methods for preparing these compounds, compositions, intermediates and derivatives thereof, and methods for treating inflammatory and serine protease mediated disorders.

Spiroimidazolidine derivatives, their preparation, their use and pharmaceutical preparations formed therefrom

The present invention relates to spiroimidazolidine derivatives of the formula I in which E, V, W, X, R1and R2have the meanings indicated in the claims. The compounds of the formula I are valuable pharmaceutical active compounds which are suitable, for example, for the therapy and prophylaxis of inflammatory disorders, such as, for example, rheumatoid arthritis, or allergic disorders. The compounds of the formula I are also inhibitors of the adhesion and migration of leukocytes and/or antagonists of the adhesion receptor VLA-4 belonging to the integrins group. They are generally suitable for the therapy and prophylaxis of illnesses which are caused by an undesired extent of leukocyte adhesion and/or leukocyte migration or are associated therewith or in which cell-cell or cell-matrix interactions which are based on interactions of VLA-4 receptors with their ligands play a part. The invention also relates to processes for the preparation of the compounds of the formula I, pharmaceutical preparations which contain compounds of the formula I, and methods for treating these disorders.

Diagnostic uses of 2-substituted adenosine carboxamides

The present invention discloses a method for measuring myocardial function in a mammal in need of such measurement by: a) administering 2-substituted adenosine carboxamide derivatives at a dosage rate of less than 1 μg/kg/min, preferably between about 0.01 and 1 μg/kg/min; and then: b) performing a technique on the mammal to detect myocardial function. The method can be used to diagnose myocardial dysfunction by electrophysiologic analysis or by imaging the vasculature of the heart, especially under conditions that simulate stress.

Cyclopentane 1-hydroxy alkyl or alkenyl-2-one or 2-hydroxy derivatives as therapeutic agents

The present invention provides a novel compound represented by the general formula I; wherein R is H or COR3;R1 is H, R2, phenyl, or COR3, wherein R2 is C1-C5 lower alkyl and R3 is R2 or phenyl;Z is CH2 or O;Y is OH or OCOR3;x is 0 or 1; andX is C1-C5 n-alkyl, C3-C7 cycloalkyl, phenyl, furanyl, thienyl or substituted derivatives thereof, wherein the substituents maybe selected from the group consisting of C1-C5 alkyl, halogen, CF3, CN, NO2, NR42, CO2R4 and OR4 wherein R4 is hydrogen or C1-C5 alkyl and dotted lines represent the presence or absence of a double bond and wavy lines represent a cis or trans bond. These novel compounds are especially useful for treating elevated intraocular pressure (ocular hypertension) and glaucoma.

N-arylsulfonylamino acid omega-amides

Compounds of the formula I: stereoisomeric forms, and physiologically tolerable salts thereof are suitable for the production of pharmaceuticals for the therapy and prophylaxis of disorders involving matrix-degrading metalloproteinases.

PYRROLYLPHENYL-SUBSTITUTED HYDROXAMIC ACID DERIVATIVES

Disclosed are the pyrrolylphenyl-substituted hydroxamic acid derivatives of the formula wherein R represents hydrogen, lower alkyl, halogen or lower alkoxy; R1 and R2 independently represent hydrogen, lower alkyl or aryl; Y represents a direct bond, lower alkylene, lower alkenylene, lower alkadienylene, (thio, sulfinyl or sulfonyl)-lower alkylene or oxy-lower alkylene; Z represents wherein R3 represents hydrogen or acyl; R4 represents lower alkyl, C3-C7-cycloalkyl, aryl or aryl-lower alkyl; or Z represents wherein R3 represents hydrogen or acyl; R5 represents lower alkyl, C3-C7-cycloalkyl, aryl, aryl-lower alkyl, amino or N-(mono-or di-lower alkyl)-amino; R6 and R7 represent hydrogen or lower alkyl; and pharmaceutically acceptable salts thereof provided that R3 represents hydrogen; which are useful as selective lipoxygenase inhibitors, methods for preparation thereof, pharmaceutical compositions comprising said compounds, and a method of inhibiting lipoxygenase and of treating diseases in mammals which are responsive to lipoxygenase inhibition using said compounds and pharmaceutical compositions comprising said compounds of the invention.

Tromethamine salt of 1-methyl-beta-oxo-alpha-(phenylcarbamoyl)-2-pyrrolepropionitrile

The present invention is concerned with the novel pharmaceutically acceptable tromethamine salt of 1-methyl-beta-oxo-alpha-(phenylcarbamoyl)-2-pyrrolepropionitrile of the formula II STR1 pharmaceutical compositions comprising said salt and a method of treating inflammatory and arthritic conditions in mammals by administering said salt to mammals in need of such treatment.

2-substituted adenosine 5'-carboxamides as antihypertensive agents

The compounds of the formula I STR1 wherein R represents hydrogen or lower alkyl; R 1 represents C 3 -C 6 -cycloalkyl optionally substituted by lower alkyl, C 3 -C 6 -cycloalkyl-lower alkyl optionally substituted by lower alkyl, bicycloalkyl, bicycloalkyl-lower alkyl, aryl, aryl-lower alkyl, aryl-C 3 -C 6 -cycloalkyl, 9-fluorenyl, diaryl-lower alkyl, 9-fluorenyl-lower alkyl, cycloalkenyl-lower alkyl, bicycloalkenyl-lower alkyl, tetrahydropyranyl-lower alkyl, tetrahydrothiopyranyl-lower alkyl or adamantyl-lower alkyl; or R 1 represents a bicyclic benzo-fused 5- or 6-membered saturated carbocyclic radical or a benzo-fused 5- or 6-membered saturated heterocyclic radical containing a heteroatom selected from oxygen and sulfur which is directly attached to the fused benzene ring, any said bicyclic radical being unsubstituted or substituted on the benzo portion by lower alkyl, lower alkoxy, hydroxy, halogen or trifluoromethyl, or by a substituent -W-Z in which W represents a direct bond, lower alkylene, lower alkenylene, thio-lower alkylene or oxy-lower alkylene and Z represents cyano, carboxy or carboxy derivatized in the form of a pharmaceutically acceptable ester or amide, or R 1 represents any said bicyclic radical substituted-lower alkyl; or R 1 represents aryl-hydroxy-lower alkyl; R 2 represents hydrogen, lower alkyl or aryl-lower alkyl; R 3 represents hydrogen or hydroxy; R 4 represents hydrogen, lower alkyl, aryl-lower alkyl, C 3 -C 6 -cycloalkyl or hydroxy-lower alkyl; aryl represents an optionally substituted carbocyclic aromatic radical, being preferably 1- or 2-naphthyl, phenyl, or naphthyl or phenyl substituted by one to three of lower alkyl, lower alkoxy, hydroxy, halogen or trifluoromethyl, or naphthyl or phenyl substituted by a substitutent -W-Z in which W represents a direct bond, lower alkylene, lower alkenylene, thio-lower alkylene or oxy-lower alkylene and Z represents cyano, carboxy or carboxy derivatized in the form of a pharmaceutically acceptable ester or amide; or aryl represents a heterocyclic aromatic radical, being preferably pyridyl or thienyl, each optionally substituted as described above for phenyl; pharmaceutically acceptable ester derivatives thereof in which free hydroxy groups are esterified in the form of a pharmaceutically acceptable ester; and pharmaceutically acceptable salts thereof; their preparation; and their use as adenosine-2 receptor agonists are disclosed.

Pyrrole-2-acetylamino acid derivative compounds

Novel pyrrole-2-acetylamino compounds of the formula: STR1 and salts thereof, wherein R" is H, alkyl, (CH2)n CO2 H, CH2 CH2 SCH3, (CH2)4 NH2 or (CH2)2 CONH2 ; and n is 1 or 2, which have the same analgesic and antiinflammatory utility as zomepirac, but with reduced liability toward gastrointestinal irritation, and esters of the compounds of the above formula which are useful as intermediates to make said compounds.