Vitamin D analogues

A compound and composition technology, applied in the field of new practical industrial products, can solve the problems of no effect on calcium metabolism and only retention of differentiation characteristics, etc.

Inactive Publication Date: 2009-08-05
GALDERMA RES & DEV SNC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Structural analogs of vitamin D are currently synthesized, some of which retain only differentiation properties and have no effect on calcium metabolism

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0189] {5-[4,(1-Ethyl-1-hydroxypropyl)biphenyl-3-yloxymethyl]-2-hydroxymethylphenyl}methanol

[0190] a) Dimethyl 4-hydroxymethylphthalate

[0191] 1,2,4-Benzenetricarboxylic anhydride (50 g, 260 mmol) was dissolved in 800 mL of anhydrous dioxane. BH3·THF (260 mmol, 1 eq.) was added dropwise using a dropping funnel at room temperature over about 1 h 30 min. Stirring was continued for 12 hours, and then the reaction solution was poured into a mixture of 600 mL of saturated ammonium chloride solution and 2 L of dichloromethane. After standing to separate the phases, the organic phase was dried and the solvent was evaporated under reduced pressure. To the obtained residue was added 5 mL of sulfuric acid, then dissolved in 1 L of methanol and heated to reflux. After refluxing for 18 hours, the reaction solution was cooled to room temperature and poured directly into a water / ether mixture (1L / 2L). After standing to separate the phases, the aqueous phase was back-extracted wit...

Embodiment 2

[0212] {2-Hydroxymethyl-5-[4'-(1-hydroxy-1-methylethyl)-biphenyl-3-yloxymethyl]phenyl}methanol

[0213] In a manner similar to Example 1(j), 3'-[3,4-bis(benzoyloxymethyl)benzyloxy Ethyl]-biphenyl-4-carboxylate (700mg, 1.16mmol) was purified by silica column chromatography to obtain a white solid (melting point 88-90°C) (m=405mg, Y=93%).

[0214] 1 HNMR (CDCl 3 ): 1.60(6H,s), 2.4(1H,bs), 3.95(2H,bs), 4.70(2H,s), 4.71(2H,s), 5.09(2H,s), 6.92(1H,dd, J 1 =2.5Hz,J 2 =7.2Hz), 7.17-7.19(2H, m), 7.30-7.38(3H, m), 7.43(1H, s), 7.54(4H, s). 13 C(DEPT)32.1(2CH 3 ), 64.1 (CH 2 ), 64.3 (CH 2 ), 70.0 (CH 2 ), 72.7 (C IV ), 113.8(CH), 114.1(CH), 120.3(CH), 125.3(2CH), 127.3(2CH), 127.7(CH), 129.1(CH), 130.2(CH), 130.3(CH), 137.5(C IV ), 139.6 (C IV ), 139.9 (C IV ), 140.5 (C IV ), 142.8 (C IV ), 149.0 (C IV ), 159.4 (C IV ).

Embodiment 3

[0216] {5-[4'-(1-Ethyl-1-hydroxypropyl)-2'-methylbiphenyl-3-yloxymethyl]-2-hydroxymethylphenyl} Methanol

[0217] (a) Ethyl 3'-hydroxy-2-methylbiphenyl-4-carboxylate

[0218] In a manner analogous to Example 1(h), 2 g (13.3 mmol) of 3-methoxymethoxy-phenylboronic acid were reacted with 1.9 g (8.9 mmol) of 3-methyl-4-bromobenzoic acid to obtain 1.6 g (74%) of desired product.

[0219] (b) 3'-[3,4-bis(benzoyloxymethyl)benzyloxy]-2-methylbiphenyl-4-carboxylic acid methyl ester

[0220] In a manner similar to Example 1(j), 1.6 g (6.6 mmol) of 3'-hydroxyl-2-methylbiphenyl-4-ethyl formate was mixed with 3.47 g (7.9 mmol) of 3,4-bis( Benzoyloxymethyl)benzyl bromide was reacted to obtain 3.7 g (94%) of 3'-[3,4-bis(1-phenylformyloxymethyl)-benzyloxy]-2-methyl Methyl biphenyl-4-carboxylate.

[0221] (c) {5-[4'-(1-ethyl-1-hydroxypropyl)-2'-methylbiphenyl-3-yloxymethyl]-2-hydroxymethylphenyl}methanol

[0222] In a manner similar to Example 1(j), 3'-[3,4-bis(benzoyloxymethyl)-benz...

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Abstract

The present invention relates to novel triaromatic compounds of the following general formula (I) and processes for their preparation and their use in human medicine or veterinary medicine (in the fields of dermatology, oncology and autoimmune diseases, especially in the field of organ or tissue transplantation) application in pharmaceutical or cosmetic compositions.

Description

[0001] This application is a divisional application of the PCT / FR00 / 03249 invention patent application entitled "Vitamin D Analogs" filed on November 22, 2000. The parent application obtained the Chinese patent application number 00818458.5. technical field [0002] The present invention relates to a novel practical industrial product, namely vitamin D analogues belonging to triaromatic compounds. The invention also relates to processes for their preparation, to their use in human or veterinary pharmaceutical compositions, or in cosmetic compositions. [0003] The compounds according to the invention have significant activity on cell proliferation and differentiation and are especially useful in the local and systemic treatment of skin diseases (or other diseases) involving keratinization disorders, diseases involving an inflammatory component and / or an immunoallergic component and Benign or malignant hyperplasia of tissues of ectodermal origin (skin, epithelium). These compo...

Claims

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Application Information

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IPC IPC(8): C07D213/30C07D333/16A61K31/4418A61K31/381A61P17/00A61P37/08A61P1/02A61P11/00A61P27/02A61P15/12A61K8/00A61K8/30A61K8/49A61K8/67A61K31/045A61K31/047A61K31/085A61K31/10A61K31/38A61K31/435A61P3/02A61P3/14A61P5/00A61P9/00A61P9/10A61P17/02A61P17/06A61P17/08A61P17/10A61P17/12A61P17/14A61P19/02A61P19/08A61P19/10A61P29/00A61P35/00A61P37/02A61P37/04A61Q5/00A61Q5/12A61Q7/00A61Q17/00A61Q19/00A61Q19/08C07C33/26C07C43/23C07C323/19C07C323/21C07D207/46C07D213/79C07D333/56
CPCA61Q19/00C07C323/19C07C33/26A61Q7/00A61K8/67C07C43/23A61Q19/08A61Q5/00A61P1/02A61P11/00A61P15/12A61P17/00A61P17/02A61P17/06A61P17/08A61P17/10A61P17/12A61P17/14A61P19/02A61P19/08A61P19/10A61P27/02A61P29/00A61P3/02A61P3/14A61P35/00A61P37/02A61P37/04A61P37/06A61P37/08A61P5/00A61P9/00A61P9/10
Inventor J·-M·伯纳多T·比亚达蒂
Owner GALDERMA RES & DEV SNC
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