GB395007A - Curative specifics containing sulphonated derivatives of santalene or caryophyllene - Google Patents
Curative specifics containing sulphonated derivatives of santalene or caryophylleneInfo
- Publication number
- GB395007A GB395007A GB27671/31A GB2767131A GB395007A GB 395007 A GB395007 A GB 395007A GB 27671/31 A GB27671/31 A GB 27671/31A GB 2767131 A GB2767131 A GB 2767131A GB 395007 A GB395007 A GB 395007A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oil
- water
- esters
- derivatives
- caryophyllene
- 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
- NPNUFJAVOOONJE-ZIAGYGMSSA-N β-(E)-Caryophyllene Chemical class C1CC(C)=CCCC(=C)[C@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-ZIAGYGMSSA-N 0.000 title abstract 10
- NVEQFIOZRFFVFW-UHFFFAOYSA-N 9-epi-beta-caryophyllene oxide Chemical class C=C1CCC2OC2(C)CCC2C(C)(C)CC21 NVEQFIOZRFFVFW-UHFFFAOYSA-N 0.000 title abstract 5
- FAMPSKZZVDUYOS-UHFFFAOYSA-N alpha-Caryophyllene Chemical class CC1=CCC(C)(C)C=CCC(C)=CCC1 FAMPSKZZVDUYOS-UHFFFAOYSA-N 0.000 title abstract 5
- NPNUFJAVOOONJE-UHFFFAOYSA-N beta-cariophyllene Chemical class C1CC(C)=CCCC(=C)C2CC(C)(C)C21 NPNUFJAVOOONJE-UHFFFAOYSA-N 0.000 title abstract 5
- NPNUFJAVOOONJE-UONOGXRCSA-N caryophyllene Chemical class C1CC(C)=CCCC(=C)[C@@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-UONOGXRCSA-N 0.000 title abstract 5
- 229940117948 caryophyllene Drugs 0.000 title abstract 5
- 150000000116 santalene derivatives Chemical class 0.000 title 1
- 239000003921 oil Substances 0.000 abstract 8
- 235000019198 oils Nutrition 0.000 abstract 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 8
- 150000002148 esters Chemical class 0.000 abstract 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 4
- 150000003873 salicylate salts Chemical class 0.000 abstract 4
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 3
- 229930195733 hydrocarbon Natural products 0.000 abstract 3
- 150000002430 hydrocarbons Chemical class 0.000 abstract 3
- LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical class CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 abstract 2
- 239000001306 (7E,9E,11E,13E)-pentadeca-7,9,11,13-tetraen-1-ol Substances 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 235000019483 Peanut oil Nutrition 0.000 abstract 2
- LSIXBBPOJBJQHN-DTORHVGOSA-N Santene Natural products C1C[C@@H]2C(C)=C(C)[C@H]1C2 LSIXBBPOJBJQHN-DTORHVGOSA-N 0.000 abstract 2
- 150000001242 acetic acid derivatives Chemical class 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 159000000011 group IA salts Chemical class 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 238000007689 inspection Methods 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 abstract 2
- 239000000312 peanut oil Substances 0.000 abstract 2
- 239000010671 sandalwood oil Substances 0.000 abstract 2
- 229930013258 santalene Natural products 0.000 abstract 2
- 229930004725 sesquiterpene Natural products 0.000 abstract 2
- 150000004354 sesquiterpene derivatives Chemical class 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- 239000000725 suspension Substances 0.000 abstract 2
- KWFJIXPIFLVMPM-UHFFFAOYSA-N α-santalene Chemical compound C1C2C3(C)C2CC1C3(C)CCC=C(C)C KWFJIXPIFLVMPM-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- -1 acetates Chemical compound 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
Classifications
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Sulphonates of the sesquiterpenes santalene or caryophyllene are prepared by adding concentrated sulphuric acid to a mixture of the hydrocarbon with acetic anhydride. Water is added to the mixture after reaction and the whole neutralized by alkali and the oil layer removed. The alkaline sulphonate is extracted from the aqueous solution with chloroform, the chloroform evaporated, the residue redissolved in water and extracted with ether to remove any remaining oil, and the aqueous solution evaporated to dryness. The Specification as open to inspection under Sect. 91 relates also to the use of esters of santalol, such as acetates, oleates, valerianates and salicylates, and the mono-santallic esters of succinic, phthalic and camphoric acids, and similar esters of caryophyllenic alcohol; of the alkaline salts and esters of the acids found in the resinous portion of oil of copaive, viz., illurinic, b -metacopaivic, p-copaivic, and homoparacopaivic acids; and of derivatives of the hydrocarbons santene and caryophyllene formed by introduction into the nucleus or side chain of groups such as nitro, nitrous, amine, or hydroxyl. The method of manufacture of the foregoing compounds is not described. The various derivatives may be administered in water or oil or insoluble derivatives may be rendered soluble in water by association with the sulphonates or salicylates. The prior use of suspension of sandal wood oil in water, or of solutions of the oil in peanut oil is referred to. This subject-matter does not appear in the Specification as accepted.ALSO:Sulphonates of the sesquiterpenes santalene and caryophyllene are prepared for use in medicine by injection or local application. The Specification as open to inspection under Sect. 91 relates also to the use of esters of santalol or of caryophallenic alcohol such as acetates, oleates, valerianates, and salicylates and the mono esters of succinic, phthalic, and camphoric acids, of alkaline salts or esters of various acids found in the resinous portion of oil of copsiva, and of derivatives of the hydrocarbons santene and caryophyllene obtained by the introduction of various substituents, such as nitro, nitrous, amine or hydroxyl, into the nucleus or side chain. The various derivatives may be administered in water or oil, and insoluble derivatives may be rendered soluble in water by association with the sulphonates or salicylates. The prior use of suspensions of sandal wood oil in water, or of solutions of the oil in peanut oil is referred to. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BR395007X | 1930-10-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB395007A true GB395007A (en) | 1933-07-05 |
Family
ID=3949189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27671/31A Expired GB395007A (en) | 1930-10-04 | 1931-10-05 | Curative specifics containing sulphonated derivatives of santalene or caryophyllene |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB395007A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002078719A1 (en) * | 2001-03-28 | 2002-10-10 | F.P.L. Pharma Inc. | Antitumor methods and compositions comprising sesquiterpene derivatives |
| WO2003020371A3 (en) * | 2001-09-05 | 2003-07-17 | F P L Pharma Inc | Potentiator composition comprising a terpene for enhancing a therapeutical effect of antitumoral agents in the treatment of cancer |
-
1931
- 1931-10-05 GB GB27671/31A patent/GB395007A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002078719A1 (en) * | 2001-03-28 | 2002-10-10 | F.P.L. Pharma Inc. | Antitumor methods and compositions comprising sesquiterpene derivatives |
| WO2003020371A3 (en) * | 2001-09-05 | 2003-07-17 | F P L Pharma Inc | Potentiator composition comprising a terpene for enhancing a therapeutical effect of antitumoral agents in the treatment of cancer |
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