GB1426370A - - Google Patents
Info
- Publication number
- GB1426370A GB1426370A GB5053273A GB5053273A GB1426370A GB 1426370 A GB1426370 A GB 1426370A GB 5053273 A GB5053273 A GB 5053273A GB 5053273 A GB5053273 A GB 5053273A GB 1426370 A GB1426370 A GB 1426370A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloride
- oleanolyl
- acetyl
- oct
- reaction
- 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
- RIXNFYQZWDGQAE-DFHVBEEKSA-N (4as,6ar,6as,6br,8ar,10s,12ar,14bs)-10-acetyloxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid Chemical compound C([C@H]1C2=CC[C@H]34)C(C)(C)CC[C@]1(C(O)=O)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](OC(=O)C)C1(C)C RIXNFYQZWDGQAE-DFHVBEEKSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 abstract 1
- MIJYXULNPSFWEK-GTOFXWBISA-N 3beta-hydroxyolean-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C MIJYXULNPSFWEK-GTOFXWBISA-N 0.000 abstract 1
- JKLISIRFYWXLQG-UHFFFAOYSA-N Epioleonolsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4CCC3C21C JKLISIRFYWXLQG-UHFFFAOYSA-N 0.000 abstract 1
- YBRJHZPWOMJYKQ-UHFFFAOYSA-N Oleanolic acid Natural products CC1(C)CC2C3=CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(C1)C(=O)O YBRJHZPWOMJYKQ-UHFFFAOYSA-N 0.000 abstract 1
- MIJYXULNPSFWEK-UHFFFAOYSA-N Oleanolinsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C MIJYXULNPSFWEK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 125000002843 carboxylic acid group Chemical group 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000002763 monocarboxylic acids Chemical class 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 229940100243 oleanolic acid Drugs 0.000 abstract 1
- RIXNFYQZWDGQAE-UHFFFAOYSA-N oleanolic acid acetate Natural products C12CC=C3C4CC(C)(C)CCC4(C(O)=O)CCC3(C)C1(C)CCC1C2(C)CCC(OC(=O)C)C1(C)C RIXNFYQZWDGQAE-UHFFFAOYSA-N 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- HZLWUYJLOIAQFC-UHFFFAOYSA-N prosapogenin PS-A Natural products C12CC(C)(C)CCC2(C(O)=O)CCC(C2(CCC3C4(C)C)C)(C)C1=CCC2C3(C)CCC4OC1OCC(O)C(O)C1O HZLWUYJLOIAQFC-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1426370 Oleanolic acid amides BIOREX LABORATORIES Ltd 10 Oct 1974 [31 Oct 1973] 50532/73 Heading C2U The invention comprises compounds of formula (wherein R is H or an acyl radical of a mono- or polycarboxylic acid, any carboxylic acid groups therein being free, esterified, or salified with a non-toxic organic or inorganic base), and their preparation from 3-esters of oleanolyl chloride with monocarboxylic acids, by reaction with N-methylpiperazine optionally followed by 3- hydrolysis and, if desired 3-esterification. 3-O-Acetyl-oleanolyl chloride is prepared from 3-O-acetyl-oleanolic acid by reaction with thionyl chloride. Antiinflammatory compositions for oral and parenteral administration comprise a compound I and a carrier.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5053273A GB1426370A (en) | 1973-10-31 | 1973-10-31 | |
| DE19742450353 DE2450353A1 (en) | 1973-10-31 | 1974-10-23 | OLEANCARBONIC ACID DERIVATIVES, THE PROCESS FOR THEIR MANUFACTURING AND PHARMACEUTICAL PRODUCTS CONTAINING THESE COMPOUNDS |
| JP49125335A JPS5077380A (en) | 1973-10-31 | 1974-10-29 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5053273A GB1426370A (en) | 1973-10-31 | 1973-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1426370A true GB1426370A (en) | 1976-02-25 |
Family
ID=10456256
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5053273A Expired GB1426370A (en) | 1973-10-31 | 1973-10-31 |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5077380A (en) |
| DE (1) | DE2450353A1 (en) |
| GB (1) | GB1426370A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020259205A1 (en) * | 2019-06-27 | 2020-12-30 | 中国药科大学 | DERIVATIVES OF OLEANOLIC ACID AND δ-OLEANOLIC ACID AND MEDICAL USE THEREOF |
-
1973
- 1973-10-31 GB GB5053273A patent/GB1426370A/en not_active Expired
-
1974
- 1974-10-23 DE DE19742450353 patent/DE2450353A1/en not_active Withdrawn
- 1974-10-29 JP JP49125335A patent/JPS5077380A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020259205A1 (en) * | 2019-06-27 | 2020-12-30 | 中国药科大学 | DERIVATIVES OF OLEANOLIC ACID AND δ-OLEANOLIC ACID AND MEDICAL USE THEREOF |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2450353A1 (en) | 1975-05-07 |
| JPS5077380A (en) | 1975-06-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |