ES2190776B1 - NEW 2-HYDROXY-6E-HYDROXYMYNESTEROIDS. PROCEDURE OF OBTAINING AND ITS APPLICATION AS CYTOTOXIC AGENTS. - Google Patents
NEW 2-HYDROXY-6E-HYDROXYMYNESTEROIDS. PROCEDURE OF OBTAINING AND ITS APPLICATION AS CYTOTOXIC AGENTS.Info
- Publication number
- ES2190776B1 ES2190776B1 ES200300931A ES200300931A ES2190776B1 ES 2190776 B1 ES2190776 B1 ES 2190776B1 ES 200300931 A ES200300931 A ES 200300931A ES 200300931 A ES200300931 A ES 200300931A ES 2190776 B1 ES2190776 B1 ES 2190776B1
- Authority
- ES
- Spain
- Prior art keywords
- sub
- side chain
- hydroxy
- cytotoxic agents
- hydroxymynesteroids
- 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 - Fee Related
Links
Landscapes
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
2-Hidroxi-6E-hidroximinoesteroides con fórmula I -en donde R{sub,1} puede ser H, OH, ceto, o alquilo (C{sub,1}-C{sub,11}) lineal o ramificado; R{sub,2} puede ser H, OH, alquilo (C{sub,1}- C{sub,11}) lineal o ramificado y ----- representa un doble enlace opcional-, preparación y uso como agentes citotóxicos: De particular interés son 3: enlace sencillo entre 1-2, R{sub,1}=ceto, {al}-OH en 2, R{sub,2} es la cadena lateral de colesterol; 4: enlace sencillo entre 1-2, R{sub,1}=ceto, {be}-OH en 2, R{sub,2} es la cadena lateral de colesterol; (5) enlace sencillo entre 1-2, R{sub,1}={al}-OH, {al}-OH en 2, R{sub,2} es la cadena lateral de colesterol; (6) enlace sencillo entre 1-2, R{sub,1}={be}-OH, {be}-OH en 2 y R{sub,2} es la cadena lateral de colesterol; (7) doble enlace entre 1-2, R{sub,1}=ceto y R{sub,2} es la cadena lateral de colesterol. A partir de colesterol mediante tosilación, epoxidación, eliminación, dihidroxilación, diacetilación y hidroximinación se obtienen 5 y 6 los cuales son oxidados a 3, 4 y 7.2-Hydroxy-6E-hydroxythinosteroids with formula I -in where R {sub, 1} may be H, OH, keto, or linear or branched (C {sub, 1} -C {sub, 11}) alkyl; R {sub, 2} can be H, OH, linear or branched (C {sub, 1} -C {sub, 11}) alkyl and ----- represents an optional double bond-, preparation and use as cytotoxic agents : Of particular interest are 3: single bond between 1-2, R {sub, 1} = keto, {al} -OH in 2, R {sub, 2} is the cholesterol side chain; 4: single bond between 1-2, R {sub, 1} = keto, {be} -OH in 2, R {sub, 2} is the cholesterol side chain; (5) single bond between 1-2, R {sub, 1} = {al} -OH, {al} -OH in 2, R {sub, 2} is the cholesterol side chain; (6) single bond between 1-2, R {sub, 1} = {be} -OH, {be} -OH at 2 and R {sub, 2} is the cholesterol side chain; (7) double bond between 1-2, R {sub, 1} = keto and R {sub, 2} is the cholesterol side chain. From cholesterol by tosylation, epoxidation, elimination, dihydroxylation, diacetylation and hydroximination, 5 and 6 are obtained which are oxidized at 3, 4 and 7.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200101747A ES2190348B1 (en) | 2001-07-19 | 2001-07-19 | NEW 6E-HYDROXYMINESTEROIDS: ITS PROCEDURE FOR OBTAINING MEDIANT SYNTHESIS FROM COMMERCIAL STEROIDS, AND ITS APPLICATION AS CYTOTOXIC AGENTS. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2190776A1 ES2190776A1 (en) | 2003-08-01 |
| ES2190776B1 true ES2190776B1 (en) | 2005-10-01 |
Family
ID=27589288
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES200300931A Expired - Fee Related ES2190776B1 (en) | 2001-07-19 | 2001-07-19 | NEW 2-HYDROXY-6E-HYDROXYMYNESTEROIDS. PROCEDURE OF OBTAINING AND ITS APPLICATION AS CYTOTOXIC AGENTS. |
| ES200101747A Expired - Fee Related ES2190348B1 (en) | 2001-07-19 | 2001-07-19 | NEW 6E-HYDROXYMINESTEROIDS: ITS PROCEDURE FOR OBTAINING MEDIANT SYNTHESIS FROM COMMERCIAL STEROIDS, AND ITS APPLICATION AS CYTOTOXIC AGENTS. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES200101747A Expired - Fee Related ES2190348B1 (en) | 2001-07-19 | 2001-07-19 | NEW 6E-HYDROXYMINESTEROIDS: ITS PROCEDURE FOR OBTAINING MEDIANT SYNTHESIS FROM COMMERCIAL STEROIDS, AND ITS APPLICATION AS CYTOTOXIC AGENTS. |
Country Status (1)
| Country | Link |
|---|---|
| ES (2) | ES2190776B1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2894968B1 (en) * | 2005-12-20 | 2008-02-22 | Trophos Sa | NOVEL CHOLEST-4-EN-3-ONE OXIME DERIVATIVES, PHARMACEUTICAL COMPOSITIONS COMPRISING THEM, AND PROCESS FOR PREPARING THE SAME |
-
2001
- 2001-07-19 ES ES200300931A patent/ES2190776B1/en not_active Expired - Fee Related
- 2001-07-19 ES ES200101747A patent/ES2190348B1/en not_active Expired - Fee Related
Non-Patent Citations (6)
| Title |
|---|
| AKHREM, A.A.; LAKHVICH, F.A.; KHRIPACH, V.A.; KOVGANKO, N.V. Beckmann rearrangement of 2alpha,3alpha-diacetoxycholest-4-en-6- one oxime. Zhurnal Organicheskoi Khimii, (1985), 21 (4), páginas 802-4, ISSN: 0514-7492, (resumen) HCAPLUS [en línea] [recuperado el 03.04.2003]. Recuperado de STN International, Columbus, Ohio (EE.UU.), Nº de acceso 1985:505206. * |
| GERVAIS, MIREILLE; TAN, LIAT. 6-Hydroximinoandrostenedione, a new specific inhibitor of estrogen biosynthesis and its effect on T47D human breast cancer cells. Anticancer Research, 1993, Vol. 13, Nº 2, páginas 383-8, ISSN 0250-7005. * |
| HOLLAND, HERBERT L. y col. Synthesis of 6-hydroximino-3-oxo steroids, a new class of aromatase inhibitor. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-organic Chemistry (1972-1999), (1992), (5), 585-7, ISSN: 0300-922X. Compuestos con RN 140421-64-3 y RN 140421-63-2, página 585, compuestos 6 y 7; páginas 585-586, esquemas 1,2. * |
| NJAR, VINCENT C.O. y col. Synthesis of 6alpha,7alpha- and 6beta,7beta-aziridinoandrost-4-ene-3,17-diones and related compounds: potential aromatase inhibitors. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-organic Chemistry, (1995), (8), 985-91, ISSN: 0300-922X. * |
| RODRIGUEZ, JAIME y col. Isolation and synthesis of the first natural 6-hydroximino-4-en-3-one-steroids from the sponges Cinachyrella spp. Tetrahedron Letters, 1997, Vol. 38, Nº 10, páginas 1833-1836, ISSN 0040-4039. * |
| SIGINOME, HIROSHI y col. Photoinduced molecular transformations. Part 149. Stereospecific photoadditions and photorearrangements of the oximes of some steroidal alpha,beta-unsaturated cyclic ketones and their deuterio derivatives. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-organic Chemistry, (1994), (21), 3239-50, ISSN: 0300-922X. Compuesto con RN 110612-22-1, página 3241, compuesto 32. * |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2190348B1 (en) | 2005-02-01 |
| ES2190348A1 (en) | 2003-07-16 |
| ES2190776A1 (en) | 2003-08-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EA200800886A1 (en) | METHOD OF OBTAINING 1-H-IMIDAZO [4,5-C] Pyridine and their analogs | |
| EA200300337A1 (en) | POLYARILKARBOXAMIDES APPLICABLE AS AN AGENTS REDUCING THE CONTENT OF LIPIDS | |
| NO20030374D0 (en) | Cyclopentanoindoles, preparations containing such compounds and treatment methods | |
| UY27522A1 (en) | PDE9 INHIBITORS FOR TREATMENT OF CARDIOVASCULAR DISORDERS | |
| GT200200069A (en) | DERIVATIVES OF MERCAPTOACETILAMIDE, PROCEDURE FOR PREPARATION AND USE | |
| EA200600621A1 (en) | DERIVATIVES OF TETRAHYDRONAPTALINE, METHOD OF THEIR PRODUCTION AND THEIR USE AS ANTI-INFLAMMATORY MEANS | |
| HK1111168A1 (en) | A PROCESS FOR THE PREPARATION OF 17-HYDROXY-6 ß,7ß,15 ß,16 ß - BISMETHYLENE-17a-PREGN-4-ENE-3-ONE-21-CARBOXYLIC ACID Y-LACTONE AND KEY-INTERMEDIATES FOR THIS PROCESS | |
| CY1110098T1 (en) | INDUSTRIAL METHOD FOR PREPARING THE 17-HYDROXY-6-BETA, 7-BETA, 15-BETA, 16-BETA-DIS-METHYLENO-3-OXO-17-HYP-17-HYP ACID AND INTERIOR KEYS FOR THIS METHOD | |
| ATE289810T1 (en) | ECTEINASCIDINE DERIVATIVES | |
| DE602005011267D1 (en) | BENZOFURAN AND BENZOTHIOPHONE DERIVATIVES SUITABLE FOR THE TREATMENT OF CARDIOVASCULAR DISEASES | |
| NO994822D0 (en) | Immunotolerant prothrombin complex preparation | |
| ATE297209T1 (en) | PODOPHYLLOTOXIN COMPOSITIONS | |
| DK1377164T3 (en) | Erythropoietin ameliorates chemotherapy-induced toxicity in vivo | |
| AR030735A1 (en) | A PROCEDURE FOR THE PRODUCTION OF A NATURAL CHAMPINON EXTRACT | |
| ITRM20010476A1 (en) | HUMAN CORNEAL EPITHELIUM SHEETS RECONSTRUCTED AND METHOD FOR THEIR OBTAINING. | |
| MEP18708A (en) | Process for the production of beraprost and its salts | |
| ES2190776B1 (en) | NEW 2-HYDROXY-6E-HYDROXYMYNESTEROIDS. PROCEDURE OF OBTAINING AND ITS APPLICATION AS CYTOTOXIC AGENTS. | |
| IL150561A0 (en) | Method for the preparation of 5-cyanophthalide | |
| EA199900790A1 (en) | METHODS OF OBTAINING PESTICIDAL INTERMEDIATE COMPOUNDS | |
| DE602006014001D1 (en) | Preparation of 2-aminothiazole-5-carboxylic acid derivatives | |
| BR0110996A (en) | Method for preparing citalopram; compound; intermediate and its pharmaceutical composition | |
| ITMI20030578A1 (en) | PROCESS AND INTERMEDIATES FOR THE PREPARATION OF EMTRICITABINE | |
| ES528774A0 (en) | PROCEDURE FOR THE PREPARATION OF ANILINE DERIVATIVES. | |
| NO20033049D0 (en) | Process for the preparation of (+/-) trans-4-p-fluorophenyl-3-hydroxymethyl-1 | |
| EA200200162A1 (en) | LIPEPEPIPEPTIDES DEACYLATION METHOD |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EC2A | Search report published |
Date of ref document: 20030801 Kind code of ref document: A1 |
|
| FG2A | Definitive protection |
Ref document number: 2190776B1 Country of ref document: ES |
|
| FD2A | Announcement of lapse in spain |
Effective date: 20211026 |