CAS: 53-39-4; (1S,3As,3Br,5As,9As,9Bs,11As)-1-Hydroxy-1,9A,11A-Trimethyl-2,3,3A,3B,4,5,5A,6,9,9B,10,11-Dodecahydroindeno[4,5-H]Isochromen-7-One

上下游产品

mestanolone 17α-methyl-1,3-seco-2-nor-5α-androstane-1,3,17α-triol 17β-hydroxy-17α-methyl-1,3-seco-2-nor-5α-androstane-1,3-diacid 1,3-dimethylester (3S,3aS,5aS,6S,7S,9aS,9bS)-7-Carboxymethyl-3-hydroxy-3,3a,6-trimethyl-dodecahydro-cyclopenta[a]naphthalene-6-carboxylic acid17,17-dimethyl-18-nor-2-oxa-5α-androst-13(14)-en-3-one

美雄诺龙置于lithium Carbonate,臭氧,Pyridinium Hydrobromide Perbromide,Lithium Bromide,Sodium Hydroxide体系中,用 甲醇,乙醇,水,N,N-二甲基甲酰胺 作为反应溶剂,化学反应 24.0H,反应生成 氧甲氢龙
参考文献:Development Of A Commercial Process To Produce Oxandrolone
标题:Development Of A Commercial Process To Produce Oxandrolone
摘要:A Manufacturing Scale Process For The Preparation Of The Anabolic Steroid Oxandrolone Was Developed. Key Elements Included The Following: The Bromination Of Methylandrostanolone With Perbromide To Give The 2-Bromoketone In Ca. 80% Yield With Minimal Dehydration,Subsequent Elimination Of The Bromide With Li2Co3/libr To Give The 2-Enone In Ca. 70% Yield With Minimal Formation Of Methyltestosterone,And An Ozonolysis Procedure To Give The Penultimate Intermediate In Ca. 90% Yield. The Overall Yield From Methylandrostanolone To Oxandrolone Using The Described Process Was 45% As Compared To The Original Searle Yield Of 8%.
DOI:10.1021/op060231B

专利信息

专利号:US-6448413-B1
优先权日:1999-06-10
标题:Process for the synthesis of a-nor-seco compounds with sterane skeleton
发明人：SANTA CSABA; TUBA ZOLTAN; MAHO SANDOR; SZELES JANOS; BALOGH GABOR; BRLIK JANOS; TRISCHLER FERENC; SZILAGYI GABRIELLA; BAKCSI ERIKA
权利人:RICHTER GEDEON VEGYESZET
摘要:The invention relates to a new process for the synthesis of 17β-hydroxy-17α-methyl-1,3-seco-2-nor-5α-androstane-3-acid derivatives of formula (I) n wherein the meaning of Z is carboxyl or formyl group and n to the new secoindoxylidene carboxylic acid derivatives of formula (II) n wherein R 1 and R 2 independently are C 1 -C 4 alkyl or alkoxy group, hydrogen or halogen atom—which are intermediates for preparing the compounds of formula (I). n The 17β-hydroxy-17α-methyl-1,3-seco-2-nor-5α-androstane-3-acid derivatives of formula (I) are intermediates in the synthesis of oxandrolon (17β-hydroxy-17α-methyl-2-oxa-5α-androstane-3-one), which is used as anabolic in therapy.

专利号:US-6583298-B1
优先权日:1999-06-10
标 题:Process for the synthesis of 17β-hydroxy-17α-methyl-2-oxa-5α-androstane-3-one
发明人：SANTA CSABA; TUBA ZOLTAN; MAHO SANDOR; SZELES JANOS; FERENCZI KATALIN; HORVATH PETER; LANCOS KRISZTINA; MESTER TAMAS; TROMPLER ARPAD
权利人:RICHTER GEDEON VEGYESZET
摘要:The invention relates to a new process for the synthesis of 17β-hydroxy-17α-methyl-2-oxa-5α-androstane-3-one of formula (I). The process according to the invention is as follows: the 17β-hydroxy-17α-ethyl-1,3-seco-2-nor-5α-androstane-1,3-diacid of formula (III) is transformed into the ring-closed 17β-hydroxy-17α-methyl-1,3-seco-2-nor-5α-androstane-1,3-diacid anhydride of formula (II) in an inert solvent or without solvent with a C 2 -C 3 alkan acid anhydride or a substituted carbodiimide of formula R 1 —Nâ•?Câ•?N—R 2 — wherein R 1 and R 2 independently are C 1 -C 6 alkyl group, C 1 -C 6 alkyl group substituted by tertiary or quaternary amino group or 1-3 phenyl group, C 5 -C 6 cycloalkyl group, aryl group substituted by 1-3 methoxy, tertiary amino, nitro, C 1 -C 4 alkyl group or 1-3 halogen atom—and the obtained compound of formula (II) is reduced regioselectively by a complex alkali metal hydride in an inert solvent The new 17β-hydroxy-17α-methyl-1,3-seco-2-nor-5α-androstane-1,3-diacid anhydride of ormula (II) is also the subject of the invention.

专利号:US-2003032817-A1
优先权日:2001-05-15
标题:Process for the synthesis of oxandrolone
发明人：CABAJ JOHN E; KAIRYS DAVID L; ZIZELMAN PAUL M
摘要:A process is disclosed for synthesizing oxandrolone 1 involving the bromination of compound 2 to obtain compound 3, followed by the highly selective de-bromination of compound 3 to obtain compound 4, followed by the oxidation of compound 4 to obtain compound 6, and finally the reduction of compound 6 to obtain oxandrolone 1.

专利号:US-7009063-B2
优先权日:2001-12-11
标题:Process for the production of oxandrolone
发明人：DESAI SHAILESHKUMAR RAMANLAL; RAY JR DAVID WAYNE; SAYED YOUSRY A
权利人:BARR LAB INC
摘要:The present invention relates to a process for the synthesis of oxandrolone from mestanolone. The process comprises the steps of: (a) oxidizing mestanolone to form 17β-hydroxy-17α-methyl-5α-androst-1-en-3-one; (b) hydroxylating the 17β-hydroxy-17α-methyl-5α-androst-1-en-3-one to form 1α, 2α, 17β-trihydroxy-17α-methylandrostan-3-one; (c) cleaving the 1α, 2α, 17β-trihydroxy-17α-methylandrostan-3-one to form 17β-hydroxy-17α-methyl-1-oxo-1,2,-seco-A-nor-5α-androstan-2-oic acid; and (d) reducing the 17β-hydroxy-17α-methyl-1-oxo-1,2,-seco-A-nor-5α-androstan-2-oic acid to form oxandrolone.

专利号:US-10413555-B2
优先权日:2014-11-25
标题:Treatment of skin atrophy with a combination of triiodothyroacetic acid (TRIAC) and dehydroepiandrosterone (DHEA)
发明人：FAERGEMANN JAN; JOHANNSSON GUDMUNDUR; OHLSSON CLAES; BATCHELLER DEREK GREGORY; JOHNSSON JÖRGEN; TÖRNELL JAN
权利人:TROPHEA DEV AB
摘要:The aim of the present study was to investigate the effect of a combination of triiodothyroacetic acid (TRIAC) and dehydroepiandrosterone (DHEA) compared with TRIAC, DHEA or placebo alone on corticosteroid induced effect on collagen synthesis in humans. Six healthy male human volunteers aged 40-65 participated. Four areas of abdominal skin were pre-treated for 3 weeks with betamethasone valerate cream. The same areas were then treated with one of the following alternatives in the same cream vehicle: TRIAC, DHEA, TRIAC+DHEA and placebo for 2 weeks. Then suction blisters were raised in each of these areas with a vacuum pump. The blister fluid from each area was collected and frozen until analysis. Analysis of amino terminal propeptide of human type I procollagen (PINP) in suction blister fluid was performed using a commercially available immunoassay (Orion Diagnostics) kit. This study has for the first time shown that a combination of TRIAC and DHEA could effectively stimulate collagen synthesis in skin pretreated with betamethasone valerate demonstrated by an increase in PINP, and that the combination was more effective than TRIAC or DHEA alone. This combination could be used to effectively treat skin atrophy in corticosteroid induced skin atrophy. It could also be used to treat skin atrophy due to other circumstances such as e. g. sun damaged skin and skin atrophy due to high age. Another interesting application would be to combine TRIAC and DHEA with a potent corticosteroid in order to prevent corticosteroid induced skin atrophy. If this combination still is effective in the treatment of eczema and psoriasis and without the risk of skin atrophy this combination will be a major breakthrough for the use of potent topical corticosteroids.

专利号:US-6333317-B1
优先权日:1997-03-28
标 题:Regulation of amyloid precursor protein (APP) expression by administration of an estrogenic compound
发明人：LEE ROBERT K K; WURTMAN RICHARD J
权利人:MASSACHUSETTS INST TECHNOLOGY
摘要:It has been discovered that lipophilic hormones that interact with cytosolic or nuclear receptors regulate APP expression and synthesis, through modification of APP mRNA stability and/or regulation of APP gene transcription and translation activities. These studies demonstrate that the treatment of brain cells with estrone or 17β-estradiol results in a reduction in the level of APP holoprotein expression, without a concomitant change in the total level of cell protein. The reduction in the level of APP holoprotein caused by estrone or 17β-estradiol is also expected to reduce the production of neurotoxic APP fragments. In as much as estrogen deficiency in postmenopausal women is associated with a higher incidence of Alzheimer's disease, this discovery opens the possibility that estrogen therapy may prevent some of the neurodegenerative and cognitive changes associated with Alzheimer's disease, aging and other disease conditions associated with such neurodegenerative and cognitive decline.