GB1194238A - Therapeutically Active Substituted Saturated and Mono- and Polyunsaturated Alkyl-Glycerylethers - Google Patents
Therapeutically Active Substituted Saturated and Mono- and Polyunsaturated Alkyl-GlycerylethersInfo
- Publication number
- GB1194238A GB1194238A GB57149/67A GB5714967A GB1194238A GB 1194238 A GB1194238 A GB 1194238A GB 57149/67 A GB57149/67 A GB 57149/67A GB 5714967 A GB5714967 A GB 5714967A GB 1194238 A GB1194238 A GB 1194238A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- prepared
- formula
- ethoxy
- methoxy
- 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
- 229920006395 saturated elastomer Polymers 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 7
- JGHSBPIZNUXPLA-UHFFFAOYSA-N 2-hydroxyhexadecanoic acid Chemical compound CCCCCCCCCCCCCCC(O)C(O)=O JGHSBPIZNUXPLA-UHFFFAOYSA-N 0.000 abstract 4
- 150000002632 lipids Chemical class 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- -1 2-ethoxy Chemical group 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- DPRAYRYQQAXQPE-UHFFFAOYSA-N 2-bromohexadecanoic acid Chemical compound CCCCCCCCCCCCCCC(Br)C(O)=O DPRAYRYQQAXQPE-UHFFFAOYSA-N 0.000 abstract 1
- PYTRBIZZZGFMSI-UHFFFAOYSA-N 2-ethoxyhexadecan-1-ol Chemical compound CCCCCCCCCCCCCCC(CO)OCC PYTRBIZZZGFMSI-UHFFFAOYSA-N 0.000 abstract 1
- KURWIEWPUMFWKP-UHFFFAOYSA-N 2-methoxyhexadecan-1-ol Chemical compound CCCCCCCCCCCCCCC(CO)OC KURWIEWPUMFWKP-UHFFFAOYSA-N 0.000 abstract 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 241000251476 Chimaera monstrosa Species 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 241001423892 Somniosus microcephalus Species 0.000 abstract 1
- 241000251778 Squalus acanthias Species 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 239000003463 adsorbent Substances 0.000 abstract 1
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 230000003217 anti-cancerogenic effect Effects 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 239000000470 constituent Substances 0.000 abstract 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- FZNMMDGZAGNHMH-UHFFFAOYSA-N ethyl 2-bromohexadecanoate Chemical compound CCCCCCCCCCCCCCC(Br)C(=O)OCC FZNMMDGZAGNHMH-UHFFFAOYSA-N 0.000 abstract 1
- OJXNMAAXQUQSHU-UHFFFAOYSA-N ethyl 2-ethoxyhexadecanoate Chemical compound CCCCCCCCCCCCCCC(OCC)C(=O)OCC OJXNMAAXQUQSHU-UHFFFAOYSA-N 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 238000001640 fractional crystallisation Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 abstract 1
- RXHIZFMFPLHZDT-UHFFFAOYSA-N hexadecyl 4-methylbenzenesulfonate Chemical compound CCCCCCCCCCCCCCCCOS(=O)(=O)C1=CC=C(C)C=C1 RXHIZFMFPLHZDT-UHFFFAOYSA-N 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- 210000004185 liver Anatomy 0.000 abstract 1
- IQHRUOSDBAXDKA-UHFFFAOYSA-N methyl 2-methoxyhexadecanoate Natural products CCCCCCCCCCCCCCC(OC)C(=O)OC IQHRUOSDBAXDKA-UHFFFAOYSA-N 0.000 abstract 1
- 230000001035 methylating effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 235000016709 nutrition Nutrition 0.000 abstract 1
- 230000035764 nutrition Effects 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 abstract 1
- 235000012239 silicon dioxide Nutrition 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
- C07C43/135—Saturated ethers containing hydroxy or O-metal groups having more than one ether bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,194,238. Alkyl-α-glyceryl ethers. ASTRA NUTRITION A.B. 15 Dec., 1967 [16 Dec., 1966], No. 57149/67. Heading C2C. The invention comprises compounds of the Formula (I) where R<SP>1</SP> and R<SP>2</SP> are the same or different and represent hydrogen or aliphatic acyl groups of at most 24 carbon atoms, one of R<SP>3</SP> and R<SP>4</SP> is hydrogen and the other is an alkoxy or alkenyloxy group of at most 7 carbon atoms and R<SP>5</SP> represents a straight or branched, saturated or mono- or poly-unsaturated aliphatic group of 4 to 21 carbon atoms. They are extracted from naturally occurring lipid products containing α-glyceryl ethers, such as liver oils from Greenland shark, dog-fish, rat-fish, by distributing the lipid product, preferably after prepurification by removal of hydrocarbons and saponifiable constituents, between two media forming separate phases comprising an operation consisting of a preferably repeated extraction using two partially miscible liquids or chromatography of the lipid product in a solvent on a solid adsorbent such as silicic acid or deactivated aluminium oxide or treating the lipid product in a solvent with a substance capable of forming inclusion compounds with some part of the glyceryl ether mixture or by fractional crystallization from a polar solvent. Compounds of Formula (I) may be prepared by reacting a compound of the formula with a compound of the formula wherein R<SP>3#1</SP>, R<SP>4#1</SP> and R<SP>5#1</SP> represent R<SP>3</SP>, R<SP>4</SP> or R<SP>5</SP> respectively or an atom or group capable of being transformed into R<SP>3</SP>, R<SP>4</SP> or R<SP>5</SP> respectively by methods known in the literature, R<SP>7</SP> represents an oxygen atom, a carbon-carbon bond or the group where R<SP>a</SP> represents hydrogen or alkyl, R<SP>b</SP> represents alkyl or aryl and R<SP>a</SP> and R<SP>b</SP> together may form a ring which may contain a hetero atom and X and Y are a pair representing the pairs of groups (a) hal, and -OM, (b) arylsulphonyl and -OM, (c) alkylsulphonyl and -OM, and (d) hydroxy and hydroxy, where that means halogen, preferably chlorine or bromine, and M is a positively charged atom or group, preferably K, Na or Li, to form a compound of the formula whereafter if any of R<SP>3#1</SP> , R<SP>4#1</SP> and R<SP>5#1</SP> differ from R<SP>3</SP>, R<SP>4</SP> and R<SP>5</SP> respectively, the differing groups are transformed into the predetermined group and whereafter the group is transformed to the group CH 2 OR<SP>1</SP>, CHOR<SP>2</SP>- by methods known in the literature. 2-Methoxy (or 2-ethoxy) hexadecyl p-toluenesulphonate is prepared by reacting p-toluenesulphonyl chloride with 2-methoxy (or 2- ethoxy) hexadecanol. 2 - Methoxy - hexadecanol - 1 is prepared by reducing with lithium aluminium hydride methyl 2-methoxy-hexadecanoate which is prepared by methylating 2-hydroxyhexadecanoic acid. 2 - Hydroxy - hexadecanoic acid is prepared by hydrolysing 2-bromohexadecanoic acid. 2 - Ethoxy - hexadecanol - 1 is prepared by reducing ethyl - 2 - ethoxy - hexadecanoate which is prepared from ethyl 2-bromohexadecanoate and sodium ethoxide. Pharmaceutical compositions comprising as active ingredient a compound of Formula (I) together with a pharmaceutically acceptable carrier are administered orally or parenterally and have anti-biotic and anti-carcinogenic activity.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE17305/66A SE347433B (en) | 1966-12-16 | 1966-12-16 | |
| US05/553,683 US4046914A (en) | 1966-12-16 | 1975-02-27 | Therapeutically active substituted saturated and mono-and polyunsaturated alkyl-glycerylethers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1194238A true GB1194238A (en) | 1970-06-10 |
Family
ID=26656095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB57149/67A Expired GB1194238A (en) | 1966-12-16 | 1967-12-15 | Therapeutically Active Substituted Saturated and Mono- and Polyunsaturated Alkyl-Glycerylethers |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS4910724B1 (en) |
| DE (1) | DE1643615C3 (en) |
| FI (1) | FI52332C (en) |
| FR (1) | FR1583764A (en) |
| GB (1) | GB1194238A (en) |
| NL (1) | NL160164C (en) |
| SE (1) | SE347433B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998052550A1 (en) * | 1997-05-22 | 1998-11-26 | Interhealth Ab | Pharmaceutical composition and use thereof |
| US11478008B2 (en) * | 2016-04-29 | 2022-10-25 | Universidad Autónoma de Madrid | Formulations comprising ratfish liver oil or a product of an enzymatic or chemical glycerolysis processing of ratfish liver oil and supercritical rosemary extract and uses thereof |
-
1966
- 1966-12-16 SE SE17305/66A patent/SE347433B/xx unknown
-
1967
- 1967-12-14 DE DE1643615A patent/DE1643615C3/en not_active Expired
- 1967-12-15 GB GB57149/67A patent/GB1194238A/en not_active Expired
- 1967-12-15 NL NL6717165.A patent/NL160164C/en active
- 1967-12-15 FI FI673357A patent/FI52332C/en active
- 1967-12-16 JP JP42080307A patent/JPS4910724B1/ja active Pending
-
1968
- 1968-03-14 FR FR1583764D patent/FR1583764A/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998052550A1 (en) * | 1997-05-22 | 1998-11-26 | Interhealth Ab | Pharmaceutical composition and use thereof |
| US11478008B2 (en) * | 2016-04-29 | 2022-10-25 | Universidad Autónoma de Madrid | Formulations comprising ratfish liver oil or a product of an enzymatic or chemical glycerolysis processing of ratfish liver oil and supercritical rosemary extract and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4910724B1 (en) | 1974-03-12 |
| DE1643615B2 (en) | 1979-01-25 |
| SE347433B (en) | 1972-08-07 |
| DE1643615C3 (en) | 1979-09-20 |
| FR1583764A (en) | 1969-12-05 |
| DE1643615A1 (en) | 1971-07-01 |
| NL6717165A (en) | 1968-06-17 |
| FI52332B (en) | 1977-05-02 |
| FI52332C (en) | 1977-08-10 |
| NL160164C (en) | 1979-10-15 |
| NL160164B (en) | 1979-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |