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United States Patent (19) 11, 3,956,316 Uskokovic Et Al

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United States Patent (19) 11, 3,956,316 Uskokovic Et Al United States Patent (19) 11, 3,956,316 Uskokovic et al. (45 May 11, 1976 54 -SUBSTITUTED-DESA-PREGNANES AND 58 Field of Search.......... 260/340.5, 340.9, 488 B, DERVATIVES THEREOF 2601586 E, 476 C, 455 R, 340.7, 389, 345.8, 3459 75 Inventors: Milan Radoje Uskokovic, Montclair; Thomas Henry Williams, Cedar Grove, both of N.J. 56 References Cited UNITED STATES PATENTS (73) Assignee: Hoffmann-La Roche Inc., Nutley, N.J. 3, 138,59 6/1964 Nomine et al................... 260/586 E 3, 55,660 fl964 Nomine ct al................... 26O1586 E 22 Fied: Dec. 26, 1973 3,296,283 fl'967 Cross............................... 26O1586 E 21 Appl. No.: 427,753 Primary Examiner-Lorraine A. Weinberger Related U.S. Application Data Assistant Examiner-Michael Shippen 60 Continuation of Ser. No. 306,496, Nov. 4, 1972, Attorney, Agent, or Firm-Samuel L. Welt; Bernard S. Pat. No. 3,830,831, which is a continuation of Ser. Leon; Richard A. Gaither No. 736,569, Junc 3, 1968, abandoned, which is a division of Ser. No. 499,094, Oct. 20, 1965, Pat. No. 57 ABSTRACT 3,574,761, which is a continuation-in-part of Ser. N. This invention is directed to l l -substituted-desA 400,206, Sept. 29, 1964, Pat. No. 3,412,107. pregnanes and derivatives thereof which are useful as intermediates in the production of 9g, 10a-known ste 52 U.S. Cl........................... 260/340.5; 260/340.7; roids of the pregnane series. These latter compounds 260/340.9; 260/345.8; 260/345.9; 260/455 can be utilized as progestational and salt-retaining R; 260/476 C; 260/488 B; 260/586 E agents. 51 Int. C.’............... C07D 317/44; C07D 317f72; CO7C 49/38; CO7C 69/14 S Claims, No Drawings 3,956,316 1. 2 11-sUBSTITUTED-DESA-PREGNANES AND It is also an object of this invention to provide novel DERVATIVES THEREOF 99,10a-steroids. The novel intermediates and processes of this inven RELATED APPLICATIONS tion are valuable and provide a new synthetic route This application is a continuation of application Ser, completely of a classical chemical nature, i.e. involving No. 306,496, filed November 14, 1972, now U.S. Pat. no photochemical reaction, for converting steroids No. 3,380,831, entitled "11-SUBSTITUTED-DESA having the normal configuration into steroidal com PREGNANES AND DERIVATIVES THEREOF", pounds possessing the unnatural 96,10a-configuration. which is a continuation of application Ser. No. O In one aspect, the novel intermediates and processes 736,569, filed June 13, 1968, now abandoned, entitled of this invention enable the preparation of 96,10a 'l-SUBSTITUTED-DESA-PREGNANES AND DE steroids of the androstane series of the formula RIVATIVES THEREOF", which is a division of appli wherein R is, individually, selected from the group cation Ser. No. 499,094, filed Oct. 20, 1965, now U.S. consisting of hydroxy and lower alkanoyloxy; R is, Pat. No. 3,574,761, entitled “INTERMEDIATES AND 5 individually, hydrogen or lower alkyl and R and PROCESSES", which is a continuation-in-part of appli R, taken together, are selected from the group cation Ser. No. 400,206, filed Sept. 29, 1964, now U.S. consisting of (176-OH, 17a-lower alkanoic acid Pat. No. 3,412, 107, entitled "INTERMEDIATES AND lactone) and oxo; R is selected from the group PROCESSES'. consisting of hydrogen, lower alkyl, hydroxy and lower alkanoyloxy; Y is selected from the group DETALED DESCRIPTION OF THE INVENTION consisting of hydrogen and lower alkyl and X is a This invention relates to novel chemical intermedi substituent in the 6- or 7-position selected from the ates and processes useful in the preparation of steroids. group consisting of hydrogen, lower alkyl, lower Natural steroids possess a 9o, 106-stereochemical con alkvlthio, lower alkanoylthio and halogen. figuration. Steroidal compounds possessing the unnatu Compounds of formula I are useful as anabolic agents. ral 9p, 10a-configuration represent a pharmaceutically 25 Other 9p,10o-androstanes, the preparation of which valuable class of compounds which, even though nu is enabled by the intermediates and processes of this merous members are known in the art, cannot be ob invention, are of the formulae tained by totally classical chemical means. In fact, the only known methods for obtaining steroids possessing 30 the unnatural 9p,10or-configuration involve at least one photochemical reaction. Such photochemical reactions involve irradiation with ultraviolet light of strong inten sity for long periods of time and, in comparison with purely chemical reactions, are very inefficient and give only small yields. 35 It is an object of the present invention to provide intermediates and processes which enable the prepara tion of 93,10a-steroids without the necessity of pro ceeding through a photochemical reaction. It is also an 40 object of this invention to provide novel intermediates and processes which will enable the further exploration of steroids having the unnatural 99,0a-configuration. lower alkenyl Rs I 3,956,316 3 wherein R, Ra, Y and X have the same meaning as term lower alkenyl comprehends.groups such as vinyl above. Compounds of formula III are useful as and the like, and the term lower alkynyl comprehends progestational agents and compounds of formula ll groups such as ethinyl and the like. Halogen compre are useful as anti-androgenic agents. hends all four halogens, i.e. iodine, bromine, chlorine In another embodiment of this invention, the novel and fluorine. compounds and intermediates provided by this inven The expression (1743-OH, 17a-lower alkanoic acid tion enable the preparation of 96,10o-steroids of the lactone)' refers to a configuration on the C-17 carbon l 7 (3-pregnane series of the formula atom illustrated as follows: - wherein W is lower alkylene, e.g. polymethylenes such as ethylene, propylene or the like. With respect to substituents in the 6- and 7-position, Y preferred compounds are those having hydrogen or lower alkyl in 6- or 7-position, and those having halo wherein Y and X have the same meaning as above; gen in the 7-position. Ra is selected from the group consisting of hydro In one aspect, this invention comprises a method for gen, lower alkyl, fluoro, hydroxy and lower al the preparation of 96,10a-androstanes of formulae kanoyloxy, R is selected from the group consisting 30 I-III and of 96, 10a-17 3-pregnanes of formulae IV-V of hydrogen and halogen; and R is selected from which comprises the hydrogenation of desA-androst-9- the group consisting of hydrogen, lower alkyl, hy en-5-ones or of desA-176-pregn-9-en-5-ones to droxy and halogen. 9£3, 10.6-desA-androstan-5-ones or 9(3,106-desA-17 g Compounds of formula IV are useful as progestational pregnan-5-ones, respectively, followed by condensa agents. 35 tion with a lower alkyl vinylketone with methyl or ethyl Other 9{3, 10a-steroids of the 17 g-pregnane series, vinyl ketone preferred (as well as substitutes therefor preparable from the novel compounds and process of such as 1-tertiary amino-3-butanone, 1-tertiary amino this invention, are of the formula 3-pentanone and quaternary ammonium salts thereof), l-Q-butan-3-one, l-Q-butan-3-one lower alkylene ketal, l-O-butan-3-ol, esterified l-Q-butan-3-ol, l-Q- butan-3-ol ether, 1,3dichlorobut-2-ene, 1,3-dichloro pent-2-ene, l-pentan-3-one, l-Q-pentan-3-one lower alkylene ketal, l-Q-pentan-3-ol, esterified 1-Q-pentan 3-ol or l-Q-pentan-3-ol ether, which condensation yields the desired 9ps, 10a-steroids. The symbol Q is is bromine, chlorine or iodine, with the former two being preferred. This invention also provides a number of different methods for the preparation of said desA androst-9-en-5-one or desA-17f8-pregn-9-en-5-one starting materials from natural steroids. In one embodiment, a steroid of the 3-oxo-androst 4-ene or 3-oxo-l79-pregn-4-ene series is subjected to an oxidative ring opening of the A-ring yielding a 5 oxo-3,5-seco-A-norandrostan-3-oic acid or a 5-oxo 3,5-seco-A-nor-17g-pregnan-3-oic acid, which 3-oic Y acid can then be converted to a mixture of a 10a-desA androstan-5-one and a 10g-desA-androstan-5-one or a wherein R'a, Rs. Y and X have the same meaning as mixture of a 10a-desA-17 3-pregnan-5-one and a 106 above. desA-17 3-pregnan-5-one. The conversion of the 3-oic Compounds of formula V are useful as salt-retaining 60 acid to the desA-compound can be effected either by agents, i.e. are useful in the treatment of Addison's pyrolysis of a salt of said 3-oic acid or via the enol disease. lactone, i.e. a 4-oxoandrost-5-en-3-one or a 4-oxo- 7f8 As used herein, the term lower alkyl comprehends pregn-5-en-3-one, which upon reaction with a Grignard both straight and branched chain saturated hydrocar reagent gives an aldol, which in turn can be converted bon groups, such as methyl, ethyl, propyl, isopropyl 65 into the desired desA-compound. The desA-compound and the like. Similarly, the term lower alkanoyl com can then be converted into the starting material desA prehends groups such as acetyl and the like, and the androst-9-en-5-one or desA-17 (3-pregn-9-en-5-one via term lower alkanoyloxy comprehends groups e.g.
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