Classifications

• • C—CHEMISTRY; METALLURGY
  • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
  • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
  • C12P7/00—Preparation of oxygen-containing organic compounds
  • C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P11/00—Drugs for disorders of the respiratory system
  • A61P11/10—Expectorants
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P11/00—Drugs for disorders of the respiratory system
  • A61P11/14—Antitussive agents

Definitions

• the present invention relates to pharmaceutical compositions having mucolytic and central antitussive activities containing as the active ingredient (-)- trans-sobrerol, namely 1R-trans-5-hydroxy- ⁇ , ⁇ ,4-trimethyl-3-cyclohexene-1-methanol, of formula (I).
• Sobrerol is a well-known drug and it has been used in therapy for a long time because of its mucolytic activity.
• Sobrerol has two asymmetric carbon atoms, therefore it is normally used in the form of a mixture of two diastereoisomer pairs of enantiomers, whose pharmacological properties have never been studied up to now.
• the invention provides pharmaceutical compositions containing (-)trans-sobrerol as the active ingredient, said compositions being useful in the tre- atment of acute and chronic bronchopulmonary patholo-gies, like bronchitis, pneumonia, bronchopneumonia, bronchiectasis and, generally, all those conditions where soothing the tussive symptomatology and/or regu- lating mucus secretion are desirable.
• compositions of the invention can be prepared according to well-known techniques and excipients, like those described in Remington's Pharmaceutical Sciences Handbook, Mack Pub. Co., N.Y., USA 17 th Ed.
• Suitable administration forms are tablets, capsu- les, sachets, syrups, solutions for the parenteral or aerosol administrations, nasal drops and the like.
• the single dose of active ingredient will range from 10 to 500 mg, while general posology will depend on several factors (pathology, patient conditions) : for instance, for an adult weighing about 70 kg a 100 to 1000 mg/day administration can be provided, optionally divided in several administrations.
• (-)-Trans-sobrerol can be prepared by means of known methods like those described in the above mentioned reference, or conventional methods for the asymmetric synthesis, the isomer separation and the optical resolution.
• a suitable method consists in using 1- ⁇ -pinene oxide as starting material.
• (-)-Trans-sobrerol may also be prepared by microbiological conversion of ⁇ -pinene and ⁇ -pinene epoxide, using a strain of Pseudomonas fluorescens, according to the following method:
• the microorganism used for producing (-)-trans-sobrerol is Pseudomonas fluorescens, whose taxonomic properties have been controlled by the National Collection of Industrial Bacteria (NCIMB, Torry Research Station, Aberdeen, UK).
• Pseudomonas fluorescens is being kept in plates with "nutrient" agar at 30°C.
• the cultures are used to inoculate Erlenmeyer flasks (250 ml) containing 50 ml of the culture medium disclosed in Table 1, and glucose (0.5% by volume) as a sole source of carbon.
• the flasks are then incubated in an orbitant mixer at 150 rpm and

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• Health & Medical Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• General Health & Medical Sciences (AREA)
• Public Health (AREA)
• General Chemical & Material Sciences (AREA)
• Pharmacology & Pharmacy (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Animal Behavior & Ethology (AREA)
• Bioinformatics & Cheminformatics (AREA)
• Veterinary Medicine (AREA)
• Medicinal Chemistry (AREA)
• Wood Science & Technology (AREA)
• Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
• Pulmonology (AREA)
• Zoology (AREA)
• Microbiology (AREA)
• Biotechnology (AREA)
• Biochemistry (AREA)
• General Engineering & Computer Science (AREA)
• Genetics & Genomics (AREA)
• Epidemiology (AREA)
• Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Medicinal Preparation (AREA)
• Preparation Of Compounds By Using Micro-Organisms (AREA)

Applications Claiming Priority (2)

Publications (1)

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Cited By (5)

Citations (3)

• 1990
  • 1990-08-22 CH CH2728/90A patent/CH681060A5/de not_active IP Right Cessation
• 1991
  • 1991-08-12 WO PCT/EP1991/001530 patent/WO1992003128A1/en not_active Ceased
  • 1991-08-12 EP EP91914459A patent/EP0496858A1/en not_active Withdrawn
  • 1991-08-12 AU AU83274/91A patent/AU8327491A/en not_active Abandoned
  • 1991-08-12 JP JP3513874A patent/JPH05502892A/ja active Pending

Patent Citations (3)

Non-Patent Citations (3)

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