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Benzoxazine and benzothiazine derivatives and parmaceutical compositions containing them

A derivative and benzo-based technology, applied in the field of benzoxazine and benzothiazine derivatives and pharmaceutical compositions containing them, can solve problems such as high CVD risk, and achieve the effect of reducing total cholesterol

Inactive Publication Date: 2005-03-16
DR REDDYS LAB LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Patients with glucose intolerance / insulin resistance in addition to hyperlipidemia have higher CVD risk

Method used

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  • Benzoxazine and benzothiazine derivatives and parmaceutical compositions containing them
  • Benzoxazine and benzothiazine derivatives and parmaceutical compositions containing them
  • Benzoxazine and benzothiazine derivatives and parmaceutical compositions containing them

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0230] According to another embodiment of the present invention, the compound of general formula (I)——Y represents oxygen; W represents -O-aryl-(CR 10 R 11 )o-NR 12 -; all other symbols as defined above - may be prepared by means of a process comprising:

[0231] Use a solvent such as CH 2 Cl 2 、CHCl 3 , chlorobenzene, benzene, THF, in the presence of catalysts such as p-toluenesulfonic acid, methanesulfonic acid, TFA, TfOH, BF 3 -OEt 2 etc., make formula (IIIi) compound

[0232]

[0233] where n and p are integers 0-6, G 1 for NH 2 or formyl, all other symbols are as defined above,

[0234] Reaction with a compound of formula (IIIh),

[0235]

[0236] where q is an integer 0-6, G 2 for NH 2 or formyl, all other symbols are as defined above. The reaction can also be performed using activated molecular sieves. The reaction temperature may be in the range of 10°C to 100°C, preferably in the range of 10°C to 60°C. Na(CN)BH can be used in solvents such as meth...

preparation example 1

[0333] Ethyl 2-ethoxy-3-(4-aminophenyl)propionate

[0334]

[0335] step (i)

[0336]From triethyl 2-ethoxyphosphonoacetate (26.5g, 1.5eq, 99.3mmol) and NaH (50% oil) (5.3g, 2eq, 132.4mmol) in THF (350ml) at 0°C Preparation of Wittig salts. To this was added solid 4-nitrobenzaldehyde (10 g, 1 eq, 66.2 mmol) in portions at 0° C., and the resulting solution was stirred at RT for 16 hours. The reaction mixture was diluted with ethyl acetate and washed with aqueous NH 4 Cl wash. The crude product contained the Z and E stereoisomers of ethyl 4-nitro-2-ethoxycinnamate (11 g).

[0337] step (ii)

[0338] At RT, in ethyl acetate (150ml), ethyl 4-nitro-2-ethoxycinnamate obtained in step (i) was washed with Pd (10%) / C-H 2 (60 psi) (11 g) was hydrogenated and purified by chromatography eluting with ethyl acetate / hexanes to afford the title compound as a viscous oil (9.41 g, 60% yield).

[0339] 1 H NMR (200MHz, CDCl 3 )δ: 1.16(t, J=7.0Hz, 3H), 1.22(t, J=7.0Hz, 3H), 2.90(d,

...

preparation example 2

[0345] 3-(3,4-Dihydro-2H-benzo[b][1,4]oxazin-4-yl)propyl bromide

[0346]

[0347] 3,4-Dihydro-2H-benzo[b][1,4]oxazine (3.0g, 1eq, 22.2mmol), 1,3-dibromopropane (22.5ml, 10eq, 222mmol) and anhydrous A mixture of sodium carbonate (7.05g, 3eq, 66.6mmol) in anhydrous DMF (200ml) was heated at 70°C for 16 hours. The reaction mixture was diluted with ethyl acetate, washed with water and brine. The residue was chromatographed eluting with ethyl acetate and hexanes to afford the title compound as a liquid (2.6 g, 47%).

[0348] 1 H NMR (200MHz, CDCl 3 )δ: 2.10-2.30(m, 2H), 3.37(t, J=4.4Hz, 2H), 3.40-3.56(m, 4H), 4.25(t, J=4.3Hz, 2H), 6.60-6.90(m , aromatic, 4H).

[0349] Mass m / z(CI): 255(M( 79 Br)), 256(M( 79 Br)+1), 257(M(Br 81 )), 258(M(Br 81 )+1)

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PUM

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Abstract

The present invention relates to novel antidiabetic, hypolipidemic, antiobesity and hypocholesterolemic compounds of formula (I) their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them, to a process for preparing such compounds. More particularly, the present invention relates to novel alkyl carboxylic acids of the general, their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them, to a process for preparing such compounds. The present invention also relates to processes for the preparation of the compounds of formula (I), novel intermediates, processes for their preparation, their use in the preparation of the above said compounds and their use as antidiabetic, hypolipidemic, antiobesity and hypocholesterolemic compounds.

Description

field of invention [0001] The present invention relates to novel antidiabetic, hypolipidemic, therapeutic obesity and hypocholesterolemic compounds, their derivatives, their analogs, their tautomeric forms, their stereoisomers, and their polymorphs Compounds, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them, relate to methods for preparing such compounds. More precisely, the present invention relates to a novel class of alkyl carboxylic acids, their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their Pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them relate to processes for preparing such compounds. [0002] The present invention also relates to novel intermediates, their preparation methods, their use in the preparation of the above-mentioned compoun...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/08A61K9/10A61K9/14A61K9/20A61K9/48A61K31/538A61K31/5415A61P1/04A61P1/14A61P1/18A61P3/04A61P3/06A61P3/10A61P9/10A61P9/12A61P13/12A61P15/00A61P17/06A61P19/10A61P21/04A61P25/28A61P29/00A61P35/00A61P43/00C07B61/00C07C227/04C07C227/18C07C229/34C07C229/42C07D265/36C07D279/16
CPCC07C229/42C07D279/16C07D265/36C07C229/34A61P1/04A61P1/14A61P1/18A61P13/12A61P15/00A61P17/06A61P19/10A61P21/04A61P25/28A61P29/00A61P3/04A61P35/00A61P3/06A61P43/00A61P9/10A61P9/12A61P3/10
Inventor D·布尼亚S·K·达斯G·R·马达范J·伊克巴勒R·查克拉巴蒂
Owner DR REDDYS LAB LTD
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