WO1992003128A1 - Compositions pharmaceutiques a activite mucolytique et antitussive contenant du (-)-trans-sobrerol - Google Patents

Compositions pharmaceutiques a activite mucolytique et antitussive contenant du (-)-trans-sobrerol Download PDF

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Publication number
WO1992003128A1
WO1992003128A1 PCT/EP1991/001530 EP9101530W WO9203128A1 WO 1992003128 A1 WO1992003128 A1 WO 1992003128A1 EP 9101530 W EP9101530 W EP 9101530W WO 9203128 A1 WO9203128 A1 WO 9203128A1
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WO
WIPO (PCT)
Prior art keywords
sobrerol
trans
mucolytic
pharmaceutical compositions
antitussive activity
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
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PCT/EP1991/001530
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English (en)
Inventor
Guillermo Bleichner
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Riace Ets
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Riace Ets
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Publication of WO1992003128A1 publication Critical patent/WO1992003128A1/fr
Anticipated expiration legal-status Critical
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    • 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)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Medicinal Preparation (AREA)

Abstract

L'invention décrit les caractéristiques pharmacologiques de 1R-trans-5-hydroxy-alpha,alpha,4-triméthyle-3-cyclohexène-1-méthanol et les compositions pharmaceutiques le contenant en tant qu'ingrédient actif.
PCT/EP1991/001530 1990-08-22 1991-08-12 Compositions pharmaceutiques a activite mucolytique et antitussive contenant du (-)-trans-sobrerol Ceased WO1992003128A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH2728/90-1 1990-08-22
CH2728/90A CH681060A5 (fr) 1990-08-22 1990-08-22

Publications (1)

Publication Number Publication Date
WO1992003128A1 true WO1992003128A1 (fr) 1992-03-05

Family

ID=4240272

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1991/001530 Ceased WO1992003128A1 (fr) 1990-08-22 1991-08-12 Compositions pharmaceutiques a activite mucolytique et antitussive contenant du (-)-trans-sobrerol

Country Status (5)

Country Link
EP (1) EP0496858A1 (fr)
JP (1) JPH05502892A (fr)
AU (1) AU8327491A (fr)
CH (1) CH681060A5 (fr)
WO (1) WO1992003128A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20030047503A (ko) * 2001-12-11 2003-06-18 진양제약주식회사 소브레롤·아세트아미노펜 복합 건조시럽제 및 액제
CN102911890A (zh) * 2011-08-05 2013-02-06 烟台海上传奇生物科技有限公司 可代谢己烯雌酚的假单胞菌及其应用
WO2017043935A1 (fr) * 2015-09-09 2017-03-16 한국생명공학연구원 Composition pour prévenir ou traiter des maladies liées à une faiblesse musculaire comprenant du sobrerol
WO2019002889A1 (fr) * 2017-06-30 2019-01-03 Industrial Technology Research Institute Procédé de traitement d'une maladie neurologique auto-immune et/ou d'une maladie neurodégénérative et formules pharmaceutiques pour une forme galénique liquide et une forme galénique à libération contrôlée
WO2025155109A1 (fr) * 2024-01-17 2025-07-24 주식회사 뉴롤메드 Composition pour le traitement d'un dysfonctionnement cognitif

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE764323A (fr) * 1970-04-17 1971-08-16 Corvi Camillo Spa Procede pour la preparation du sobrerol emploi pharmaceutique, du sobrerol ainsi obtenu
EP0170839A2 (fr) * 1984-08-08 1986-02-12 CAMILLO CORVI S.p.A. Mélange de composés diastéréoisomères obtenus à partir de la (-)-5-(1-hydroxy-1-méthyléthyle)-2-méthyle-2-cyclohexène-1-one ayant une activité mucosécrétolytique. Procédé de préparation et compositions pharmaceutiques les contenant
DD262874A1 (de) * 1987-07-31 1988-12-14 Akad Wissenschaften Ddr Verfahren zur mikrobiellen transformation von alpha-pinenen zu verbenolen

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE764323A (fr) * 1970-04-17 1971-08-16 Corvi Camillo Spa Procede pour la preparation du sobrerol emploi pharmaceutique, du sobrerol ainsi obtenu
EP0170839A2 (fr) * 1984-08-08 1986-02-12 CAMILLO CORVI S.p.A. Mélange de composés diastéréoisomères obtenus à partir de la (-)-5-(1-hydroxy-1-méthyléthyle)-2-méthyle-2-cyclohexène-1-one ayant une activité mucosécrétolytique. Procédé de préparation et compositions pharmaceutiques les contenant
DD262874A1 (de) * 1987-07-31 1988-12-14 Akad Wissenschaften Ddr Verfahren zur mikrobiellen transformation von alpha-pinenen zu verbenolen

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Applied Microbiology and Biotechnology, volume 23, no. 3/4, January 1986, Springer-Verlag, S.J. Wright et al.: "Microbial oxidation of alpha-pinene by serratia marcescens", pages 224-227, see the whole article *
Patentjoernaal, December 1978, page 131, & ZA, A, 77/7442 (CAMILLO CORVI S.P.A.) *
Zeitschrift der Chemie, volume 28, no. 3, 1988, L. Weber et al.: "Mikrobielle oxydation von alpha-pinen mit acetobacter methanolicus", pages 98-99, see the whole article *

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20030047503A (ko) * 2001-12-11 2003-06-18 진양제약주식회사 소브레롤·아세트아미노펜 복합 건조시럽제 및 액제
CN102911890A (zh) * 2011-08-05 2013-02-06 烟台海上传奇生物科技有限公司 可代谢己烯雌酚的假单胞菌及其应用
CN102911890B (zh) * 2011-08-05 2014-06-04 烟台海上传奇生物科技有限公司 可代谢己烯雌酚的假单胞菌及其应用
US10765642B2 (en) 2015-09-09 2020-09-08 Korea Research Institute Of Bioscience And Biotechnology Composition for preventing or treating muscle weakness-related diseases comprising sobrerol
WO2017043935A1 (fr) * 2015-09-09 2017-03-16 한국생명공학연구원 Composition pour prévenir ou traiter des maladies liées à une faiblesse musculaire comprenant du sobrerol
CN108601755A (zh) * 2015-09-09 2018-09-28 韩国生命工学研究院 用于预防或治疗肌无力相关疾病的、包含水合蒎醇的组合物
CN108601755B (zh) * 2015-09-09 2021-08-10 韩国生命工学研究院 用于预防或治疗肌无力相关疾病的、包含水合蒎醇的组合物
CN111107843A (zh) * 2017-06-30 2020-05-05 财团法人工业技术研究院 用于治疗自体免疫神经疾病及/或神经退化性疾病的方法以及用于液体剂型与控制释放剂型的药物制剂
WO2019002889A1 (fr) * 2017-06-30 2019-01-03 Industrial Technology Research Institute Procédé de traitement d'une maladie neurologique auto-immune et/ou d'une maladie neurodégénérative et formules pharmaceutiques pour une forme galénique liquide et une forme galénique à libération contrôlée
US11400054B2 (en) 2017-06-30 2022-08-02 Industrial Technology Research Institute Method for treating an autoimmune neurological disease and/or neurodegenerative disease and pharmaceutical formulations for a liquid dosage form and a controlled release dosage form
US20220249395A1 (en) * 2017-06-30 2022-08-11 Industrial Technology Research Institute Pharmaceutical formulations for a liquid dosage form and a controlled release dosage form
TWI779059B (zh) * 2017-06-30 2022-10-01 財團法人工業技術研究院 化合物用於製備治療自體免疫神經疾病及/或神經退化性疾病之藥物的用途
CN111107843B (zh) * 2017-06-30 2024-01-09 财团法人工业技术研究院 化合物用于制备治疗自体免疫神经疾病及/或神经退化性疾病的药物的用途以及其液体剂型与控释剂型的药物制剂
TWI830180B (zh) * 2017-06-30 2024-01-21 財團法人工業技術研究院 化合物之液體劑型的醫藥配方
WO2025155109A1 (fr) * 2024-01-17 2025-07-24 주식회사 뉴롤메드 Composition pour le traitement d'un dysfonctionnement cognitif

Also Published As

Publication number Publication date
CH681060A5 (fr) 1993-01-15
AU8327491A (en) 1992-03-17
EP0496858A1 (fr) 1992-08-05
JPH05502892A (ja) 1993-05-20

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