C07D307/58

Andrographolide compound and method for treatment or prevention of fibrotic disease using the same

A compound represented by formula I or II. R.sub.1 and R.sub.2 are at each occurrence selected from the group consisting of hydrogen, methyl, phenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,4,5-trimethoxyphenyl, 2-hydroxyphenyl, 3-hydroxyphenyl, 4-hydroxyphenyl, 2-fluorophenyl, 2-chlorophenyl, 2-bromophenyl, 3-fluorophenyl, 3-chlorophenyl, 3-bromophenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 2-fluoro-3-methoxyphenyl, 3-methoxy-4-chlorophenyl, 2,4-difluorophenyl, 2,4-dichlorophenyl, 2,4-dibromophenyl, 2-fluoro-4-chlorophenyl, 2-bromo-4-chlorophenyl, 3-fluoro-4-chlorophenyl, 3-bromo-4-chlorophenyl, 3,4-difluorophenyl, 3,4-dichlorophenyl, 3,4-dibromophenyl, 2-chloro-4-fluorophenyl, 2-bromo-4-fluorophenyl, 3-chloro-4-fluorophenyl, 3-bromo-4-fluorophenyl, 2-fluoro-4-bromophenyl, 2-chloro-4-bromobenzene group, 3-fluoro-4-bromophenyl, 3-chloro-4-bromophenyl, 2,3,4-trichlorophenyl, 2-methoxy-4-chlorophenyl, 2-hydroxy-4-chlorophenyl, 2-hydroxy-4-methoxyphenyl, 3-fluoro-4-(4-methylpiperazinyl)phenyl, 4-(N,N-dimethylamino)phenyl, and 3-fluoro-4-(4-morpholinyl)phenyl. R.sub.3 and R.sub.4 are hydrogen, or R.sub.3 and R.sub.4 are at each occurrence selected from the group consisting of —CH.sub.2CH.sub.2COOH, —CH.sub.2CH.sub.2CH.sub.2CH.sub.2COOH, —CH.sub.2CH═CHCH.sub.2COOH, and —CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2COOH; or R.sub.3 and R.sub.4 are —COR.sub.5, and R.sub.5 is selected from the group consisting of 3-pyridyl, —CH.sub.2CH.sub.2COOH, —CH.sub.2CH.sub.2CH.sub.2CH.sub.2COOH, —CH.sub.2CH═CHCH.sub.2COOH, and —CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2COOH.

Andrographolide compound and method for treatment or prevention of fibrotic disease using the same

A compound represented by formula I or II. R.sub.1 and R.sub.2 are at each occurrence selected from the group consisting of hydrogen, methyl, phenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,4,5-trimethoxyphenyl, 2-hydroxyphenyl, 3-hydroxyphenyl, 4-hydroxyphenyl, 2-fluorophenyl, 2-chlorophenyl, 2-bromophenyl, 3-fluorophenyl, 3-chlorophenyl, 3-bromophenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 2-fluoro-3-methoxyphenyl, 3-methoxy-4-chlorophenyl, 2,4-difluorophenyl, 2,4-dichlorophenyl, 2,4-dibromophenyl, 2-fluoro-4-chlorophenyl, 2-bromo-4-chlorophenyl, 3-fluoro-4-chlorophenyl, 3-bromo-4-chlorophenyl, 3,4-difluorophenyl, 3,4-dichlorophenyl, 3,4-dibromophenyl, 2-chloro-4-fluorophenyl, 2-bromo-4-fluorophenyl, 3-chloro-4-fluorophenyl, 3-bromo-4-fluorophenyl, 2-fluoro-4-bromophenyl, 2-chloro-4-bromobenzene group, 3-fluoro-4-bromophenyl, 3-chloro-4-bromophenyl, 2,3,4-trichlorophenyl, 2-methoxy-4-chlorophenyl, 2-hydroxy-4-chlorophenyl, 2-hydroxy-4-methoxyphenyl, 3-fluoro-4-(4-methylpiperazinyl)phenyl, 4-(N,N-dimethylamino)phenyl, and 3-fluoro-4-(4-morpholinyl)phenyl. R.sub.3 and R.sub.4 are hydrogen, or R.sub.3 and R.sub.4 are at each occurrence selected from the group consisting of —CH.sub.2CH.sub.2COOH, —CH.sub.2CH.sub.2CH.sub.2CH.sub.2COOH, —CH.sub.2CH═CHCH.sub.2COOH, and —CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2COOH; or R.sub.3 and R.sub.4 are —COR.sub.5, and R.sub.5 is selected from the group consisting of 3-pyridyl, —CH.sub.2CH.sub.2COOH, —CH.sub.2CH.sub.2CH.sub.2CH.sub.2COOH, —CH.sub.2CH═CHCH.sub.2COOH, and —CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2COOH.

A METHOD FOR DIRECTLY CONSTRUCTING HIGHLY OPTICALLY ACTIVE TETRASUBSTITUTED ALLENIC ACID COMPOUNDS
20220064096 · 2022-03-03 · ·

The present invention discloses a method for directly constructing highly optically active tetrasubstituted allenic acid compounds, i.e., a one-step process for directly constructing highly optically active axially chiral tetrasubstituted allenic acid compounds by using tertiary propargyl alcohol, carbon monoxide and water as reactants in an organic solvent in the presence of palladium catalyst, chiral diphosphine ligand, monophosphine ligand and organic phosphoric acid. The method of the present invention has the following advantages: operations are simple, raw materials and reagents are readily available, the reaction conditions are mild, the substrate has high universality, the functional group has good compatibility, and the reaction has high enantioselectivity (90%˜>99% ee). The highly optically active allenic acid compounds obtained by the present invention can be used as an important intermediate to construct γ-butyrolactone compounds containing tetrasubstituted chiral quaternary carbon centers, tetrasubstituted allenic alcohol and other compounds.

ENANTIOSELECTIVE SYNTHESIS OF BRIVARACETAM AND INTERMEDIATES THEREOF

The present invention relates to an improved and economical process for enantioselective synthesis and purification of a novel key intermediate of Brivaracetam. Further, the present invention also relates to a process for the preparation of a chirally pure Brivaracetam of formula I utilizing the said intermediate.

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MODIFIED ORGANOMETALLIC FRAMEWORK AND CATALYST FOR HYDROGENATION REACTION INCLUDING SAME

The present disclosure relates to an organometallic framework modified using a compound having a hydroxyl group (—OH), a catalyst for a hydrogenation reaction including the same, and a method of manufacturing the same. The catalyst according to the present disclosure has high activity to the hydrogenation reaction even at a low temperature of 30 to 40° C., thus making low-grade waste heat usable.

MODIFIED ORGANOMETALLIC FRAMEWORK AND CATALYST FOR HYDROGENATION REACTION INCLUDING SAME

The present disclosure relates to an organometallic framework modified using a compound having a hydroxyl group (—OH), a catalyst for a hydrogenation reaction including the same, and a method of manufacturing the same. The catalyst according to the present disclosure has high activity to the hydrogenation reaction even at a low temperature of 30 to 40° C., thus making low-grade waste heat usable.

Method for producing ϵ-caprolactam

A method produces ε-caprolactam through adipamide as an intermediate, and characteristically includes a lactamization step of reacting adipamide, formed from a material compound, with hydrogen and ammonia in the presence of a catalyst containing: a metal oxide mainly containing an oxide(s) of one or more metallic elements selected from the group consisting of metallic elements of group 5 and groups 7 to 14 in the 4th to 6th periods of the periodic table; and a metal and/or a metal compound having a hydrogenation ability.

Plant growth regulator compounds

The present invention relates to relates to novel strigolactone derivatives of formula (I), to processes for preparing these derivatives including intermediate compounds, to seeds comprising these derivatives, to plant growth regulator or seed germination promoting compositions comprising these derivatives and to methods of using these derivatives in controlling the growth of plants and/or promoting the germination of seeds. ##STR00001##

Plant growth regulator compounds

The present invention relates to relates to novel strigolactone derivatives of formula (I), to processes for preparing these derivatives including intermediate compounds, to seeds comprising these derivatives, to plant growth regulator or seed germination promoting compositions comprising these derivatives and to methods of using these derivatives in controlling the growth of plants and/or promoting the germination of seeds. ##STR00001##

PURIFIED FORMS OF ROFECOXIB, METHODS OF MANUFACTURE AND USE

The subject matter disclosed herein relates to rofecoxib, also known as TRM-201 or RXB-201, its method of manufacture, and use. In certain aspects, the highly pure or substantially pure rofecoxib as provided herein has a favorable purity profile and is the active ingredient in a pharmaceutical composition that is administered to treat or prevent a number of conditions, including pain associated with a condition caused by a bleeding disorder.