Preparation and utility of substituted carboxylic acid compounds

A compound and mixture technology, applied in the fields of application, anhydride/acid/halide active ingredients, botany equipment and methods, etc., can solve problems such as adverse events and complex applications

Inactive Publication Date: 2009-08-19
AUSPEX PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, their use in polypharmacy is necessarily complicated and has proven potential for adverse events

Method used

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  • Preparation and utility of substituted carboxylic acid compounds
  • Preparation and utility of substituted carboxylic acid compounds
  • Preparation and utility of substituted carboxylic acid compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0322] d 13 -2-(4-Isobutyl-phenyl)-propionic acid (d 13 - ibuprofen)

[0323]

[0324] D in thick wall pressure pipe 2 A mixture of ibuprofen (206 mg, 1.00 mmol) in O (5 mL) was treated with 10% Pd / C (20 mg) and washed with N 2 Bubble deoxygenation. Sodium formate (102 mg, 1.5 equiv) was added and the tube was then capped and surrounded by a blast shield. The temperature was raised to 160°C and held for 24 hours. After cooling to ambient temperature, the tube was uncapped, then the reaction mixture was diluted with diethyl ether, and 1 N HCl (2 eq.) was added. Separate the organic layer, anhydrous MgSO 4 Drying and concentration under reduced pressure gave a white solid (163 mg). This operation was repeated for 143 mg of the above product to give a white solid (127 mg, 66% for two steps). 1 H NMR (300MHz, CDCl 3 , 4-chloro-1-methoxy-2-nitrobenzene was used as internal standard) 7.12 (d, 2H), 7.23 (d, 2H).

Embodiment 2

[0326] d 17 -2-(4-Isobutyl-phenyl)-propionic acid (d 17 - ibuprofen)

[0327]

[0328] Prepared according to Sajiki, 2005. d in a closed tube under hydrogen pressure in the presence of 5% Pt / C (20 wt% of substrate) 13 - ibuprofen in D 2 O heated to 180 ° C.

Embodiment 3

[0330] 2-(6-Hydroxynaphthalen-2-yl)-propionic acid

[0331]

[0332] A mixture of naproxen (1.15 g, 5.00 mmol) in glacial acetic acid (10 mL) was treated with 48% aqueous HBr (2.5 mL) and heated to 150 °C for 3 hours. Most of the solvent and acid were distilled off, and the mixture was cooled to room temperature. The resulting solid was washed with H 2 O (20 mL), stirred for 30 minutes, filtered, and washed with H 2 Washed with O and hexane, and dried under reduced pressure to give an off-white solid (1.038 g, 4.80 mmol, 96%). 1 H NMR (300MHz, acetone-d 6 ) 1.63 (d, 3H), 3.62 (s, 3H), 3.90 (q, 2H), 7.18 (m, 2H), 7.41 (m, 1H), 7.67 (m, 1H), 7.78 (m, 2H).

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Abstract

The present disclosure is directed to modulators of cyclooxygenase (COX) enzymes and pharmaceutically acceptable salts and prodrugs thereof, the chemical synthesis thereof, and the medical use of such compounds for the treatment and / or management of the severity and duration of non-specific pain, tension-type pain, headache, migraine, lower back pain, sciatica, dental pain, muscular pain, pain associated with acute soft tissue injuries, bursitis, tendonitis, lumbago, periarthritis, tennis elbow, sprains, strains, muscular problems associated with sports injuries, muscular problems associated with accidents, period pain, primary dysmenorrhoea, acute sore throat pain, osteoarthritis, rheumatoid arthritis, cancer, any disorder requiring analgesic response, any disorder requiring anti- inflammatory response, any disorder requiring antipyretic response, any conditions mediated by cyclooxygenase, cystic fibrosis, dementia, Alzheimer's disease, and / or conditions mediated by levels of beta-amyloid are described.

Description

[0001] related application [0002] This application claims the benefit of US Provisional Patent Application No. 60 / 809,107, filed May 26, 2006, and US Provisional Patent Application No. 60 / 841,367, filed August 30, 2006. field of invention [0003] The present invention relates to modulators of cyclooxygenase (COX) and pharmaceutically acceptable salts and prodrugs thereof, their chemical synthesis, and describe the use of such compounds in the treatment and / or management of non-specific pain, tension-type pain, Headache, migraine, lower back pain, sciatica, toothache, muscle pain, pain associated with acute soft tissue injury, bursitis, tendinitis, low back pain, periarthritis, tennis elbow, Sprain, strain, muscle problems related to sports injuries, muscle problems related to accidents, period pain, primary menstrual pain, acute sore throat, osteoarthritis, rheumatoid arthritis , cancer, any condition requiring an analgesic response, any condition requiring an anti-inflamm...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N37/10A61K31/19A61K9/20
Inventor T·G·甘特S·萨沙S·H·吴
Owner AUSPEX PHARMA INC
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