Title:
METHODS OF MAKING THE 4-N-BUTYLCYCLOHEXANOIC AND THE UNDECANOIC ACID ESTERS OF (7 ALPHA, 11 BETA)-DIMETHYL-17 BETA-HYDROXY-4-ESTREN-3-ONE AND THEIR MEDICAL USE
Document Type and Number:
WIPO Patent Application WO2001074839
Kind Code:
A3
Abstract:
Methods of using 7 alpha ,11 beta -dimethyl-17 beta -hydroxy-4-estren-3-one bucyclate (I) and 7 alpha ,11 beta -dimethyl-17 beta -hydroxyestr-4-en-3-one 17-undecanoate (II) for various hormonal therapies, dosage forms comprising 7 alpha ,11 beta -dimethyl-17 beta -hydroxy-4-estren-3-one bucyclate and 7 alpha ,11 beta -dimethyl-17 beta -hydroxyestr-4-en-3-one 17-undecanoate, and processes for their preparation.
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Inventors:
BLYE RICHARD P (US)
KIM HYUN K (US)
KIM HYUN K (US)
Application Number:
PCT/US2001/010293
Publication Date:
June 13, 2002
Filing Date:
March 30, 2001
Export Citation:
Assignee:
US GOV HEALTH & HUMAN SERV (US)
BLYE RICHARD P (US)
KIM HYUN K (US)
BLYE RICHARD P (US)
KIM HYUN K (US)
International Classes:
A61K9/10; A61K31/56; A61K31/565; A61K9/08; A61K31/566; A61K31/57; A61P5/26; A61P5/30; A61P15/00; A61P15/10; A61P15/16; A61P21/06; C07B61/00; C07J1/00; C07J21/00; C07J71/00; (IPC1-7): A61K31/565; A61P15/16; A61P5/26
Domestic Patent References:
| WO1999026962A1 | 1999-06-03 |
Other References:
DAVIDSON D W ET AL: "Increasing circulating androgens with oral testosterone undecanoate in eugonadal men", CHEMICAL ABSTRACTS + INDEXES, AMERICAN CHEMICAL SOCIETY. COLUMBUS, US, vol. 13, no. 107, 28 September 1987 (1987-09-28), pages 91, XP002082921, ISSN: 0009-2258
TAEUBER U ET AL: "ABSOLUTE BIOAVAILABILITY OF TESTOSTERONE AFTER ORAL ADMINISTRATION OF TESTOSTERONE-UNDECANOATE AND TESTOSTERONE.", EUR J DRUG METAB PHARMACOKINET, (1986) 11 (2), 145-150., XP001056949
PARTSCH, CARL-JOACHIM ET AL: "Injectable testosterone undecanoate has more favourable pharmacokinetics and pharmacodynamics than testosterone enanthate.", EUROPEAN JOURNAL OF ENDOCRINOLOGY, (1995) VOL. 132, NO. 4, PP. 514-519., XP001057806
ZITZMANN, M. ET AL: "Hormone substitution in male hypogonadism.", MOLECULAR AND CELLULAR ENDOCRINOLOGY, (MARCH 30, 2000) VOL. 161, NO. 1-2, PP. 73-88., XP001057049
NIESCHLAG E ET AL: "PLASMA ANDROGEN LEVELS IN MEN AFTER ORAL ADMINISTRATION OF TESTOSTERONE OR TESTOSTERONE UNDECANOATE.", ACTA ENDOCRINOL, (1975) 79 (2), 366-374., XP001056933
"The Merck Index, 11th Edition", 1989, MERCK & CO., INC., RAHWAY, N.J., USA, XP002191464
"Rote Liste", 1996, ECV EDITIO CANTOR, AULENDORF/WÜRTT, XP002191465
MONDER, CARL (1) ET AL: "Studies on the metabolism of testosterone trans-4-n-butylcyclohexanoic acid in the cynomolgus monkey, Macaca fascicularis.", JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, (1994) VOL. 50, NO. 5-6, PP. 305-311., XP001056954
MONDER, C. (1) ET AL: "Metabolism of testosterone trans-4-n-butylcyclohexyl carboxylate, a high potency androgen, in rodents and primates: In vitro studies.", JOURNAL OF ENDOCRINOLOGY, (1994) VOL. 140, NO. 3, PP. 465-473., XP001056952
TAEUBER U ET AL: "ABSOLUTE BIOAVAILABILITY OF TESTOSTERONE AFTER ORAL ADMINISTRATION OF TESTOSTERONE-UNDECANOATE AND TESTOSTERONE.", EUR J DRUG METAB PHARMACOKINET, (1986) 11 (2), 145-150., XP001056949
PARTSCH, CARL-JOACHIM ET AL: "Injectable testosterone undecanoate has more favourable pharmacokinetics and pharmacodynamics than testosterone enanthate.", EUROPEAN JOURNAL OF ENDOCRINOLOGY, (1995) VOL. 132, NO. 4, PP. 514-519., XP001057806
ZITZMANN, M. ET AL: "Hormone substitution in male hypogonadism.", MOLECULAR AND CELLULAR ENDOCRINOLOGY, (MARCH 30, 2000) VOL. 161, NO. 1-2, PP. 73-88., XP001057049
NIESCHLAG E ET AL: "PLASMA ANDROGEN LEVELS IN MEN AFTER ORAL ADMINISTRATION OF TESTOSTERONE OR TESTOSTERONE UNDECANOATE.", ACTA ENDOCRINOL, (1975) 79 (2), 366-374., XP001056933
"The Merck Index, 11th Edition", 1989, MERCK & CO., INC., RAHWAY, N.J., USA, XP002191464
"Rote Liste", 1996, ECV EDITIO CANTOR, AULENDORF/WÜRTT, XP002191465
MONDER, CARL (1) ET AL: "Studies on the metabolism of testosterone trans-4-n-butylcyclohexanoic acid in the cynomolgus monkey, Macaca fascicularis.", JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, (1994) VOL. 50, NO. 5-6, PP. 305-311., XP001056954
MONDER, C. (1) ET AL: "Metabolism of testosterone trans-4-n-butylcyclohexyl carboxylate, a high potency androgen, in rodents and primates: In vitro studies.", JOURNAL OF ENDOCRINOLOGY, (1994) VOL. 140, NO. 3, PP. 465-473., XP001056952
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