GB1468758A - Industrial process for the synthesis of 2,6-dihydroxy-cineole through pinol from highly pure sobrerol products thus obtained and use thereof in pharmaceutical field - Google Patents
Industrial process for the synthesis of 2,6-dihydroxy-cineole through pinol from highly pure sobrerol products thus obtained and use thereof in pharmaceutical fieldInfo
- Publication number
- GB1468758A GB1468758A GB2409074A GB2409074A GB1468758A GB 1468758 A GB1468758 A GB 1468758A GB 2409074 A GB2409074 A GB 2409074A GB 2409074 A GB2409074 A GB 2409074A GB 1468758 A GB1468758 A GB 1468758A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pinol
- cineole
- dihydroxy
- sobrerol
- synthesis
- 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.)
- Expired
Links
- SKBXVAOMEVOTGJ-UHFFFAOYSA-N xi-Pinol Chemical compound CC1=CCC2C(C)(C)OC1C2 SKBXVAOMEVOTGJ-UHFFFAOYSA-N 0.000 title abstract 7
- OMDMTHRBGUBUCO-IUCAKERBSA-N (1s,5s)-5-(2-hydroxypropan-2-yl)-2-methylcyclohex-2-en-1-ol Chemical compound CC1=CC[C@H](C(C)(C)O)C[C@@H]1O OMDMTHRBGUBUCO-IUCAKERBSA-N 0.000 title abstract 4
- 229960005233 cineole Drugs 0.000 title abstract 3
- 229960000230 sobrerol Drugs 0.000 title abstract 2
- OMDMTHRBGUBUCO-UHFFFAOYSA-N trans-sobrerol Natural products CC1=CCC(C(C)(C)O)CC1O OMDMTHRBGUBUCO-UHFFFAOYSA-N 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 239000011707 mineral Substances 0.000 abstract 2
- 150000007522 mineralic acids Chemical class 0.000 abstract 2
- 150000007524 organic acids Chemical class 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 230000001989 choleretic effect Effects 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- -1 pinol epoxide Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Gastroenterology & Hepatology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Steroid Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
1468758 Preparation of 2,6-dihydroxycineole CAMILLO CORVI SpA 30 May 1974 [12 June 1973 10 April 1974] 24090/74 Heading C2C Very pure 2,6-dihydroxy-cineole is prepared by reacting very pure sobrerol with a mineral or organic acid to give pinol, reacting the pinol with a peracid to give pinol epoxide of at least 98% purity and hydrolysing this in aqueous or aqueous/alcoholic solution using a mineral or organic acid. The processes may be illustrated by the reaction sequence: Pharmaceutical compositions having choleretic activity comprise the 2,6-dihydroxy-cineole prepared by the above process together with a suitable carrier or diluent.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2512773 | 1973-06-12 | ||
| IT2120574 | 1974-04-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1468758A true GB1468758A (en) | 1977-03-30 |
Family
ID=26327823
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4347676A Expired GB1469921A (en) | 1973-06-12 | 1974-05-30 | Industrial processes for the synthesis of 2,6-dibromocineole and 2,6-dihydroxycineole products thus obtained and use thereof in the pharmaceutical field |
| GB2409074A Expired GB1468758A (en) | 1973-06-12 | 1974-05-30 | Industrial process for the synthesis of 2,6-dihydroxy-cineole through pinol from highly pure sobrerol products thus obtained and use thereof in pharmaceutical field |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4347676A Expired GB1469921A (en) | 1973-06-12 | 1974-05-30 | Industrial processes for the synthesis of 2,6-dibromocineole and 2,6-dihydroxycineole products thus obtained and use thereof in the pharmaceutical field |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5944316B2 (en) |
| AR (2) | AR202410A1 (en) |
| CH (1) | CH605965A5 (en) |
| DE (2) | DE2462947C2 (en) |
| ES (1) | ES427240A1 (en) |
| GB (2) | GB1469921A (en) |
| NL (3) | NL176745C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4554366A (en) * | 1982-09-13 | 1985-11-19 | Shell Oil Company | Certain substituted, 7-oxabicyclo[2.2.1]heptan-2-ols and -2-ones as intermediates |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4542244A (en) * | 1982-09-13 | 1985-09-17 | Shell Oil Company | Oxabicycloalkane herbicides |
-
1974
- 1974-05-28 AR AR253955A patent/AR202410A1/en active
- 1974-05-30 CH CH746374A patent/CH605965A5/xx not_active IP Right Cessation
- 1974-05-30 GB GB4347676A patent/GB1469921A/en not_active Expired
- 1974-05-30 GB GB2409074A patent/GB1468758A/en not_active Expired
- 1974-06-11 DE DE2462947A patent/DE2462947C2/en not_active Expired
- 1974-06-11 DE DE2428039A patent/DE2428039C3/en not_active Expired
- 1974-06-12 NL NLAANVRAGE7407862,A patent/NL176745C/en not_active IP Right Cessation
- 1974-06-12 JP JP49066122A patent/JPS5944316B2/en not_active Expired
-
1975
- 1975-04-18 AR AR258428A patent/AR202506A1/en active
-
1976
- 1976-05-14 ES ES427240A patent/ES427240A1/en not_active Expired
-
1984
- 1984-11-14 NL NL8403477A patent/NL8403477A/en not_active Application Discontinuation
- 1984-11-14 NL NL8403481A patent/NL8403481A/en not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4554366A (en) * | 1982-09-13 | 1985-11-19 | Shell Oil Company | Certain substituted, 7-oxabicyclo[2.2.1]heptan-2-ols and -2-ones as intermediates |
Also Published As
| Publication number | Publication date |
|---|---|
| AR202506A1 (en) | 1975-06-13 |
| ES427240A1 (en) | 1976-09-01 |
| DE2428039B2 (en) | 1980-10-30 |
| GB1469921A (en) | 1977-04-06 |
| NL8403481A (en) | 1985-03-01 |
| NL8403477A (en) | 1985-03-01 |
| NL7407862A (en) | 1974-12-16 |
| DE2462947C2 (en) | 1986-08-28 |
| JPS5944316B2 (en) | 1984-10-29 |
| NL176745B (en) | 1985-01-02 |
| DE2428039C3 (en) | 1981-12-24 |
| NL176745C (en) | 1985-06-03 |
| CH605965A5 (en) | 1978-10-13 |
| DE2428039A1 (en) | 1975-01-09 |
| AR202410A1 (en) | 1975-06-06 |
| JPS5035155A (en) | 1975-04-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |