CH681060A5 - - Google Patents

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Publication number
CH681060A5
CH681060A5 CH2728/90A CH272890A CH681060A5 CH 681060 A5 CH681060 A5 CH 681060A5 CH 2728/90 A CH2728/90 A CH 2728/90A CH 272890 A CH272890 A CH 272890A CH 681060 A5 CH681060 A5 CH 681060A5
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Switzerland
Prior art keywords
sep
sobrerol
trans
head col
title
Prior art date
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CH2728/90A
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German (de)
Inventor
Guillermo Bleichner
Original Assignee
Riace Ets
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Application filed by Riace Ets filed Critical Riace Ets
Priority to CH2728/90A priority Critical patent/CH681060A5/de
Priority to EP91914459A priority patent/EP0496858A1/en
Priority to JP3513874A priority patent/JPH05502892A/en
Priority to PCT/EP1991/001530 priority patent/WO1992003128A1/en
Priority to AU83274/91A priority patent/AU8327491A/en
Publication of CH681060A5 publication Critical patent/CH681060A5/de

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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

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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)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (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)
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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

Pharmacological characteristics of 1R-trans-5-hydroxy- alpha , alpha ,4-trimethyl-3-cyclohexene-1-methanol and pharmaceutical compositions containing it as the active ingredient are described.

Description

       

  
 



  Gegenstand der Erfindung sind mukolytisch- und zentralantitusisch-aktive pharmazeutische Zusammensetzungen, die als Hauptaktivanteil (-)-trans-Sobrerol (1R-trans-5-hydroxy- alpha , alpha ,4-trimethyl-3-cyklohexen-1-methanol) enthalten. 



  Sobrerol ist ein bekanntes pharmazeutisches Mukolytikum, das in der Therapie schon lange wegen seiner mukolytischen Wirkung angewendet wird. 



  Sobrerol, dessen Formel nachstehend angegeben ist, besteht aus zwei asymmetrischen Kohlenstoffatomen und stellt daher ein Gemisch aus zwei diastereoisomeren und enantiomeren Paaren dar, von dem sich ergeben hat, dass bislang seine pharmakologischen Eigenschaften noch nicht untersucht wurden. 
EMI1.1
 



  Die chemisch-physikalischen Eigenschaften der Sobrerol-Enantiomere wurden jedoch untersucht (Congr. Int. Technol. Pharm. 1989 Vol. I 232-40, Chem Abstr. 112 (8) 62485). 



  Man hat nun festgestellt, dass das (-)-trans-Sobrerol des Enantiomers in bezug auf das Razematsobrerol günstige pharmakologische Eigenschaften besitzt, und es sich insbesondere durch eine geringere Toxizität  und eine völlig überraschende antitoxische Wirkung auf zentralem Niveau auszeichnet, was bislang beim Razematsobrerol weder beschrieben wurde noch bekannt war. 



  Die Erfindung gibt somit pharmazeutische Zusammensetzungen an, die als Hauptwirkstoff (-)-trans-Sobrerol enthalten, das für die pathologische Behandlung von akuten und chronischen, bronchopulmonaren Erkrankungen wie Bronchitis, Lungenentzündungen, Bronchopneumonien, Bronchiektroven und ganz allgemein, von allen solchen Fällen in denen eine Sedierung symptomatologischen Hustens und/oder eine Regelung der Schleimausscheidung gewünscht wird, anwendbar ist. 



  Die Zusammensetzungen gemäss der Erfindung können durch Anwendung bekannter Techniken bzw. Bindetechniken hergestellt werden, wie etwa jener, wie sie beschrieben sind in Remingtons Pharmaceutical Science Handbook, Mack Pub. Co., N.Y., USA, 17a Ed. 



  Geeignete Verabreichungsformen sind Kapseln, Tabletten, Pulver in Tütchen, Sirupe, parenteral oder in Form von Aerosolen verabreichbare Lösungen, Nasentropfen und dergleichen. Die Einheitsdosis der Hauptwirksubstanz kann zwischen 10 bis 500 mg variieren, wogegen die allgemeine Posologie von mehreren Faktoren abhängt (Pathologie, Zustand des Patienten): bei einem Erwachsenen mit einem Gewicht von 70 kg kann man im allgemeinen 100 bis 1000 mg pro Tag verabreichen, eventuell aufgeteilt auf mehrere Male. 



  (-)-trans-Sobrerol kann mit bekannten Verfahren hergestellt werden, wie beispielsweise jenen, die in der erstgenannten Veröffentlichung beschrieben wurden, oder  mit den konventionellen asymmetrischen Syntheseverfahren, der Isomertrennung und optischen Ausflösung. Ein bekanntes Verfahren sieht die Verwendung von 1- alpha -Pinenoxyd als Ausgangsstoff vor. 



  Nützliche Hinweise zur Herstellung von (-)-trans-Sobrerol finden sich beispielsweise in Helv. Chim. Acta 1987, 70(1), 71-8. 



  Nachstehend werden die Ergebnisse pharmakologischer Tests im Vergleich zu Razematsobrerol angegeben. 
<tb><TABLE> Columns=4 
<tb>Title: Akute Toxizität 
<tb>Head Col 01 AL=L: Verbindung 
<tb>Head Col 02 AL=L: DL 50 i.p.
bei Mäusen 
<tb>Head Col 03 AL=L: DL 50 oral
bei Mäusen 
<tb>Head Col 04 AL=L: DL 50 e.v.
bei Mäusen 
<tb> <SEP>(-)-trans-Sobrerol <SEP>5000 mg/kg <SEP>5000 mg/kg 
<tb> <SEP>Razematsobrerol <SEP>2550 mg/kg <SEP>1100 mg/kg 
<tb></TABLE> 
<tb><TABLE> Columns=4 
<tb>Title: Mukolytische Wirksamkeit
(Mawatarimethode: Mawatari H.

  Kagashima Daigaku-Zesshi 27,561; 1976) 
<tb>Head Col 01 AL=L: Verbindung 
<tb>Head Col 02 AL=L: Anzahl Tiere 
<tb>Head Col 03 AL=L: Verabreichte Dosis
mg/kg/os 
<tb>Head Col 04 AL=L: % Durchmesser von Fl Na
in bezug auf Kontrollen 
<tb> <SEP>(-)-trans-Sobrerol <SEP>10 <SEP>500 <SEP>46,4 
<tb> <SEP>Razematsobrerol <SEP>10 <SEP>500 <SEP>33,4 
<tb></TABLE> 
<tb><TABLE> Columns=5 
<tb>Title: Antitoxische Wirksamkeit 
<tb>Head Col 01 AL=L: Behandlung 
<tb>Head Col 02 AL=L: Anzahl Tiere 
<tb>Head Col 03 AL=L: Dosis
mg/kg/ip 
<tb>Head Col 04 to 05 AL=L: Huster 
<tb>SubHead Col 04 AL=L>Mittel: 
<tb>SubHead Col 05 AL=L>% Verhinderung verglichen mit Kontrollen: 
<tb> <SEP>Kontrollen <SEP>12 <SEP>- <SEP>12,4 <SEP>- 
<tb> <SEP>Rezematsobrerol <SEP>12 <SEP>250 <SEP>9,8 <SEP>20,9 
<tb> <SEP>(-)-trans-Sobrerol <SEP>12 <SEP>250 <SEP>3,7 <SEP>70,2 
<tb></TABLE> 


 Studenttest 
 



  Die nachfolgenden Beispiele dienen zur Illustration der Erfindung 
<tb><TABLE> Columns=5 
<tb>Title: 1) Kapseln 
<tb>Head Col 03 AL=L: A 
<tb>Head Col 04 AL=L: B 
<tb>Head Col 05 AL=L: C 
<tb> <SEP>(-)-trans-Sobrerol <SEP>mg <SEP>100 <SEP>200 <SEP>300 
<tb> <SEP>Laktose <SEP>mg <SEP>12 <SEP>24 <SEP>36 
<tb> <SEP>Malzdextrin <SEP>mg <SEP>6 <SEP>16 <SEP>24 
<tb> <SEP>Polyvinylpirrolidon <SEP>mg <SEP>7 <SEP>14 <SEP>21 
<tb> <SEP>Magnesiumsstearat <SEP>mg <SEP>2 <SEP>4 <SEP>6 
<tb></TABLE> 
<tb><TABLE> Columns=5 
<tb>Title: 2) Suppositorien 
<tb> <SEP>(-)-trans-Sobrerol <SEP>mg <SEP>20 <SEP>100 <SEP>200 
<tb> <SEP>Glyzeride <SEP>mg <SEP>800 <SEP>1000 <SEP>1600 
<tb></TABLE> 
<tb><TABLE> Columns=5 
<tb>Title:

   3) Pulver 
<tb> <SEP>(-)-trans-Sobrerol <SEP>mg <SEP>100 <SEP>200 <SEP>300 
<tb> <SEP>Aromate <SEP>mg <SEP>110 <SEP>220 <SEP>330 
<tb> <SEP>Zitronensäure <SEP>mg <SEP>5 <SEP>10 <SEP>15 
<tb> <SEP>Saccharin <SEP>mg <SEP>4 <SEP>8 <SEP>12 
<tb> <SEP>Aspartam <SEP>mg <SEP>5 <SEP>10 <SEP>15 
<tb> <SEP>Polysorbat 20 <SEP>mg <SEP>1,5 <SEP>3 <SEP>4,5 
<tb> <SEP>Sorbitol <SEP>mg <SEP>750 <SEP>1500 <SEP>2250 
<tb></TABLE> 
<tb><TABLE> Columns=4 
<tb>Title: 4) Sirup 
<tb> 
<tb>Head Col 01 to 04 AL=L: 100 ml Sirup enthalten 
<tb> <SEP>(-)-trans-Sobrerol <SEP>mg <SEP>1000 <SEP>2000 
<tb> <SEP>Saccharose <SEP>mg <SEP>40 <SEP>40 
<tb> <SEP>Methyl-p-Hydroxibenzoat <SEP>mg <SEP>200 <SEP>200 
<tb> <SEP>Balsamaroma <SEP>mg <SEP>200 <SEP>200 
<tb> <SEP>Reinwasser q.b.

   <SEP>ml <SEP>100 <SEP>100 
<tb></TABLE> 
<tb><TABLE> Columns=4 
<tb>Title: 5) Elixier 
<tb>Head Col 01 to 04 AL=L: 100 ml Elixier enthalten 
<tb> <SEP>(-)-trans-Sobrerol <SEP>mg <SEP>1000 <SEP>2000 
<tb> <SEP>Saccharose <SEP>mg <SEP>40 <SEP>40 
<tb> <SEP>Äthylalkohol <SEP>mg <SEP>10 000 <SEP>10 000 
<tb> <SEP>Balsamextrakt <SEP>mg <SEP>1000 <SEP>1000 
<tb> <SEP>Methyl-p-Hydroxibenzoat <SEP>mg <SEP>100 <SEP>100 
<tb> <SEP>Reinwasser q.b. <SEP>ml <SEP>100 <SEP>100 
<tb></TABLE> 
<tb><TABLE> Columns=4 
<tb>Title: 6) Ampullen 
<tb> <SEP>(-)-trans-Sobrerol <SEP>mg <SEP>30 <SEP>60 
<tb> <SEP>Reinwasser q.b. <SEP>ml <SEP>2 <SEP>4 
<tb></TABLE> 
<tb><TABLE> Columns=4 
<tb>Title: 7) Aerosolampulle 
<tb> <SEP>(-)-trans-Sobrerol <SEP>mg <SEP>30 
<tb> <SEP>Reinwasser q.b. <SEP>ml <SEP>3 <SEP>3 
<tb></TABLE> 



  
 



  The invention relates to mucolytically and centrally antitusically active pharmaceutical compositions which contain (-) - trans-sobrerol (1R-trans-5-hydroxy-alpha, alpha, 4-trimethyl-3-cyclohexene-1-methanol) as the main active component.



  Sobrerol is a well-known pharmaceutical mucolytic that has been used in therapy for a long time because of its mucolytic effect.



  Sobrerol, the formula of which is given below, consists of two asymmetric carbon atoms and is therefore a mixture of two diastereoisomeric and enantiomeric pairs, which has been shown to have so far not been studied for its pharmacological properties.
EMI1.1
 



  However, the chemical-physical properties of the sobrerol enantiomers were examined (Congr. Int. Technol. Pharm. 1989 Vol. I 232-40, Chem Abstr. 112 (8) 62485).



  It has now been found that the (-) - trans-sobrerol of the enantiomer has favorable pharmacological properties with respect to the razematsobrerol, and it is characterized in particular by a lower toxicity and a completely surprising antitoxic effect at a central level, which has hitherto neither been the case with the razematsobrerol was described was still known.



  The invention thus provides pharmaceutical compositions containing (-) - trans-sobrerol as the main active ingredient, which is suitable for the pathological treatment of acute and chronic bronchopulmonary diseases such as bronchitis, pneumonia, bronchopneumonia, bronchiectroven and in general, of all such cases in which sedation of symptomatological cough and / or regulation of mucus excretion is applicable.



  The compositions according to the invention can be made using known techniques or binding techniques, such as those described in Remington's Pharmaceutical Science Handbook, Mack Pub. Co., N.Y., USA, 17a Ed.



  Suitable forms of administration are capsules, tablets, powders in sachets, syrups, parenterally or in the form of aerosols administrable solutions, nasal drops and the like. The unit dose of the main active substance can vary between 10 to 500 mg, whereas the general posology depends on several factors (pathology, patient's condition): in an adult weighing 70 kg, it is generally possible to administer 100 to 1000 mg per day, possibly divided into several times.



  (-) - Trans-sobrerol can be prepared by known methods, such as those described in the former publication, or by the conventional asymmetric synthesis methods, isomer separation and optical resolution. A known method provides for the use of 1-alpha -pine oxide as the starting material.



  Helv. Chim, for example, provides useful information on the production of (-) - trans-sobrerol. Acta 1987, 70 (1), 71-8.



  The results of pharmacological tests compared to razematsobrerol are given below.
<tb> <TABLE> Columns = 4
<tb> Title: Acute toxicity
<tb> Head Col 01 AL = L: connection
<tb> Head Col 02 AL = L: DL 50 i.p.
in mice
<tb> Head Col 03 AL = L: DL 50 oral
in mice
<tb> Head Col 04 AL = L: DL 50 e.v.
in mice
<tb> <SEP> (-) - trans-sobrerol <SEP> 5000 mg / kg <SEP> 5000 mg / kg
<tb> <SEP> Razematsobrerol <SEP> 2550 mg / kg <SEP> 1100 mg / kg
<tb> </TABLE>
<tb> <TABLE> Columns = 4
<tb> Title: Mucolytic effectiveness
(Mawatari method: Mawatari H.

  Kagashima Daigaku-Zesshi 27.561; 1976)
<tb> Head Col 01 AL = L: connection
<tb> Head Col 02 AL = L: number of animals
<tb> Head Col 03 AL = L: dose administered
mg / kg / os
<tb> Head Col 04 AL = L:% diameter of Fl Na
in terms of controls
<tb> <SEP> (-) - trans-sobrerol <SEP> 10 <SEP> 500 <SEP> 46.4
<tb> <SEP> Razematsobrerol <SEP> 10 <SEP> 500 <SEP> 33.4
<tb> </TABLE>
<tb> <TABLE> Columns = 5
<tb> Title: Antitoxic effectiveness
<tb> Head Col 01 AL = L: treatment
<tb> Head Col 02 AL = L: number of animals
<tb> Head Col 03 AL = L: dose
mg / kg / ip
<tb> Head Col 04 to 05 AL = L: Huster
<tb> SubHead Col 04 AL = L> Medium:
<tb> SubHead Col 05 AL = L>% prevention compared to controls:
<tb> <SEP> controls <SEP> 12 <SEP> - <SEP> 12.4 <SEP> -
<tb> <SEP> Rezematsobrerol <SEP> 12 <SEP> 250 <SEP> 9.8 <SEP> 20.9
<tb> <SEP> (-) - trans-sobrerol <SEP> 12 <SEP> 250 <SEP> 3.7 <SEP> 70.2
<tb> </TABLE>


 Student test
 



  The following examples serve to illustrate the invention
<tb> <TABLE> Columns = 5
<tb> Title: 1) capsules
<tb> Head Col 03 AL = L: A
<tb> Head Col 04 AL = L: B
<tb> Head Col 05 AL = L: C
<tb> <SEP> (-) - trans-sobrerol <SEP> mg <SEP> 100 <SEP> 200 <SEP> 300
<tb> <SEP> lactose <SEP> mg <SEP> 12 <SEP> 24 <SEP> 36
<tb> <SEP> malt dextrin <SEP> mg <SEP> 6 <SEP> 16 <SEP> 24
<tb> <SEP> polyvinylpyrrolidone <SEP> mg <SEP> 7 <SEP> 14 <SEP> 21
<tb> <SEP> Magnesium stearate <SEP> mg <SEP> 2 <SEP> 4 <SEP> 6
<tb> </TABLE>
<tb> <TABLE> Columns = 5
<tb> Title: 2) suppositories
<tb> <SEP> (-) - trans-sobrerol <SEP> mg <SEP> 20 <SEP> 100 <SEP> 200
<tb> <SEP> Glyceride <SEP> mg <SEP> 800 <SEP> 1000 <SEP> 1600
<tb> </TABLE>
<tb> <TABLE> Columns = 5
<tb> Title:

   3) powder
<tb> <SEP> (-) - trans-sobrerol <SEP> mg <SEP> 100 <SEP> 200 <SEP> 300
<tb> <SEP> Aromate <SEP> mg <SEP> 110 <SEP> 220 <SEP> 330
<tb> <SEP> citric acid <SEP> mg <SEP> 5 <SEP> 10 <SEP> 15
<tb> <SEP> Saccharin <SEP> mg <SEP> 4 <SEP> 8 <SEP> 12
<tb> <SEP> Aspartame <SEP> mg <SEP> 5 <SEP> 10 <SEP> 15
<tb> <SEP> polysorbate 20 <SEP> mg <SEP> 1.5 <SEP> 3 <SEP> 4.5
<tb> <SEP> Sorbitol <SEP> mg <SEP> 750 <SEP> 1500 <SEP> 2250
<tb> </TABLE>
<tb> <TABLE> Columns = 4
<tb> Title: 4) Syrup
<tb>
<tb> Head Col 01 to 04 AL = L: 100 ml syrup included
<tb> <SEP> (-) - trans-sobrerol <SEP> mg <SEP> 1000 <SEP> 2000
<tb> <SEP> sucrose <SEP> mg <SEP> 40 <SEP> 40
<tb> <SEP> Methyl p-hydroxibenzoate <SEP> mg <SEP> 200 <SEP> 200
<tb> <SEP> Balsam Flavor <SEP> mg <SEP> 200 <SEP> 200
<tb> <SEP> pure water q.b.

   <SEP> ml <SEP> 100 <SEP> 100
<tb> </TABLE>
<tb> <TABLE> Columns = 4
<tb> Title: 5) Elixir
<tb> Head Col 01 to 04 AL = L: 100 ml elixir included
<tb> <SEP> (-) - trans-sobrerol <SEP> mg <SEP> 1000 <SEP> 2000
<tb> <SEP> sucrose <SEP> mg <SEP> 40 <SEP> 40
<tb> <SEP> ethyl alcohol <SEP> mg <SEP> 10,000 <SEP> 10,000
<tb> <SEP> balsam extract <SEP> mg <SEP> 1000 <SEP> 1000
<tb> <SEP> Methyl p-hydroxibenzoate <SEP> mg <SEP> 100 <SEP> 100
<tb> <SEP> pure water q.b. <SEP> ml <SEP> 100 <SEP> 100
<tb> </TABLE>
<tb> <TABLE> Columns = 4
<tb> Title: 6) Ampoules
<tb> <SEP> (-) - trans-sobrerol <SEP> mg <SEP> 30 <SEP> 60
<tb> <SEP> pure water q.b. <SEP> ml <SEP> 2 <SEP> 4
<tb> </TABLE>
<tb> <TABLE> Columns = 4
<tb> Title: 7) Aerosol ampoule
<tb> <SEP> (-) - trans-sobrerol <SEP> mg <SEP> 30
<tb> <SEP> pure water q.b. <SEP> ml <SEP> 3 <SEP> 3
<tb> </TABLE>

Claims (2)

1. Pharmazeutische Präparate mit mukolytischer und hustenreizlindernder Wirkung enthaltend als Hauptwirkmittel (-)-trans-Sobrerol in einem Gemisch mit einem pharmazeutisch annehmbaren Träger.         1. Pharmaceutical preparations with mucolytic and antitussive effects containing as main active ingredient (-) - trans-sobrerol in a mixture with a pharmaceutically acceptable carrier. 2. Verwendung von (-)-trans-Sobrerol zur Herstellung eines pharmazeutischen Präparates mit mukolytischer und hustenreizlindernder Wirkung nach Anspruch 1. 2. Use of (-) - trans-sobrerol for the production of a pharmaceutical preparation with mucolytic and antitussive effect according to claim 1.  
CH2728/90A 1990-08-22 1990-08-22 CH681060A5 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CH2728/90A CH681060A5 (en) 1990-08-22 1990-08-22
EP91914459A EP0496858A1 (en) 1990-08-22 1991-08-12 Pharmaceutical compositions with mucolytic and antitussive activity containing (-)-trans-sobrerol
JP3513874A JPH05502892A (en) 1990-08-22 1991-08-12 Pharmaceutical composition with mucolytic activity and antitussive activity containing (-)-trans-sobrerol
PCT/EP1991/001530 WO1992003128A1 (en) 1990-08-22 1991-08-12 Pharmaceutical compositions with mucolytic and antitussive activity containing (-)-trans-sobrerol
AU83274/91A AU8327491A (en) 1990-08-22 1991-08-12 Pharmaceutical compositions with mucolytic and antitussive activity containing (-)-trans-sobrerol

Applications Claiming Priority (1)

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

Publications (1)

Publication Number Publication Date
CH681060A5 true CH681060A5 (en) 1993-01-15

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Country Status (5)

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EP (1) EP0496858A1 (en)
JP (1) JPH05502892A (en)
AU (1) AU8327491A (en)
CH (1) CH681060A5 (en)
WO (1) WO1992003128A1 (en)

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KR20030047503A (en) * 2001-12-11 2003-06-18 진양제약주식회사 Sobrerol ·acetaminophen combined dry syrup and solution
CN102911890B (en) * 2011-08-05 2014-06-04 烟台海上传奇生物科技有限公司 Pseudomonas capable of metabolizing diethylstilbestrol and application thereof
CN108601755B (en) * 2015-09-09 2021-08-10 韩国生命工学研究院 Composition for preventing or treating myasthenia-related diseases comprising pinol hydrate
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

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Publication number Priority date Publication date Assignee Title
CH568951A5 (en) * 1970-04-17 1975-11-14 Corvi Camillo Spa
IT1180220B (en) * 1984-08-08 1987-09-23 Corvi Camillo Spa MIXTURE OF DIASTEREOISOMER COMPOUNDS, OBTAINED FROM (-) - 5- (1-HYDROXY-1-METHYL ETHYL) -2-METHYL-2-CYCLOESEN-1-ONE, HAVING MUCOSECRETOLYTIC ACTIVITY, PROCEDURE FOR ITS PREPARATION AND PHARMACEUTICAL COMPOSITIONS THAT CONTAIN
DD262874A1 (en) * 1987-07-31 1988-12-14 Akad Wissenschaften Ddr PROCESS FOR MICROBIAL TRANSFORMATION OF ALPHA PINENES TO VERBENOLES

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Publication number Publication date
JPH05502892A (en) 1993-05-20
WO1992003128A1 (en) 1992-03-05
EP0496858A1 (en) 1992-08-05
AU8327491A (en) 1992-03-17

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