18 Norsteroids as selectively active estrogens

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Cyclopentanohydrophenanthrene ring system doai

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C552S613000, C552S625000, C552S628000, C552S629000, C552S630000

Reexamination Certificate

active

06958327

ABSTRACT:
The invention relates to novel 18-norsteroids (gonatrienes) of general formula (I), wherein R1, R2, R3, R6, R7, R8, R9, R11, R11′, R14, R15, R15′, R16, R17and R17′have the meaning cited in the description, and to the use of said compounds as pharmaceutical active ingredients. Said compounds exhibit a high affinity in vitro for estrogen receptor preparations of rat prostate and in an estrogen receptor preparation of rat uterus. Said compounds exhibit in vivo preferential activity on bones as compared to the uterus and/or significant activity with regard to stimulating the expression of 5HT2a-receptors and transporter molecules. The invention also relates to the production of said compounds, therapeutic use and galenic form of said compounds contained in the novel compounds of invention. The invention also relates to utilization of steroids based on the gonatriene molecular skeleton in order to treat estrogen deficiency-induced diseases and disorders, in addition to the use of said gonatriene structural component in the total structure of compounds which dissociate to produce enhanced estrogen activity in bone as compared to the uterus

REFERENCES:
patent: 3016389 (1962-01-01), Johns
patent: 3407219 (1968-10-01), Chinn
patent: 3574197 (1971-04-01), Prezewowsky et al.
patent: 3578829 (1971-05-01), Stein et al.
patent: 3755384 (1973-08-01), Browne et al.
patent: 4605649 (1986-08-01), Liehr
patent: 4705783 (1987-11-01), Crowe et al.
patent: 1298974 (1972-12-01), None
patent: WO 0063228 (2000-10-01), None
William Johns, “Retropinacol Rearrangement of Estradiol 3-methyl Ether.” J. Organic Chemistry, 26, pp. 4583-4591, 1961.
Ivanova, et al., “Some Chemical Transformations or methyl ether of cis-18-nor-delta-9(11)-estra-15, 17-dione” Chemical Abstracts, vol. 63, No. 5, Abstract No. 5705c, (1965).
W.F. Johns, , “Retropinacol Rearrangement of Estradiol 3-Methyl Ether”; Journal of Organic Chemistry, Bd. 26, 1961, pp. 4583-4591, p. 4584; Examples 19, 20.
R. A. Edgren, et al., “Estrogenic Effects of 18-nor-17-beta.estradiol and 18-nore-estrone”, Chemical Abstracts vol. 55, No. 6, Abstract No. 5754f (1961).
W.F. Johns, “Synthesis of 18,19-Dinor Steroids”; Journal of the American Chemical Society., Bd. 80, Nr. 23, (1958), pp. 6456-6457.
Kanazawa, Gilchi; “Clinical Effect of a Contraceptive, Sophia 32”, Chemical Abstracts, Acceptance No. 72:18893 (1969).
Haihnel, Roland, et al.: “Specificity of the Estrogen Receptor of Human Uterus”; J. Steroid Biochem (1973), 4(1), 21-31.
Haihnel, Ronald, et al.: “Steroid Specificity of the Estrogen Receptor of Human Breast Carcinoma”; J. Steroid Biochem, (1974), 5(2), 119-22.
Kuhl, Alexander, et al.: 17.alpha.-(r-Chlorobenzoyloxy)-3-methoxy-13.alpha.-gona-1, 3, 5(10)-triene, ACTA Crystallogr., Sect. C: Cryst; Struct. Commun. (1998), C54(4), 521-523.
M. M. Coombs: “Potentially Carinogenic Cyclopenta'alphenanthrenes(1,2-cyclopenten ophenanthranes). Part 1. A New Synthesis of 15, 16-Dihydro-17-oxo--cyclopenta'alphenanth rene and the Phenanthrene Analogue of 18-Norestrone Methyl Ether”, Journal of the Chemical Society, Section C: Organic Chemistry., Nr. 10,(1966), 955-962.
Li Jonathan, J. et al., “Carcinogenic Activities of Various Steroidal and Nonsterioidal Estrogens in the Hamster Kindney: Relation to Hormonal Activity and Cell Proliferation”, Cancer Research, Bd. 55, Nr. 19 (1995), pp. 4347-4351.
Dence Carmen S., et al: Carbon-11-labeled Estrogens as Potential Imaging Agents for Breast Tumors; Nuclear Medicine and Biology, Bd. 23, Nr. 4 (1996), pp. 491-496.
Lobaccaro Carole, et al: “Steroidal Affinity Labels of the Estrogen Receptor: 3. Estradiol 11-beta-n-alkyl Derivatives Bearing a Terminal Electrophilic Group: Antiestrogenic and Cytotoxic Properties”; Journal of Medicinal Chemicstry, Bd. 40, Nr. 14 (1997), pp. 2217-2227.
Napolitano, et al.: “11.beta.-Substituted Estradiol Derivatives; Potential High-Affinity Carbo-11-Labeled Probes for the Estrogen Receptor: A Structure-Affinity Relationship Study”; Journal of Medicinal Chemistry, Bd. 38, Nr. 3 (1995), pp. 429-434.
Tedesco, R., et al., “7alpha,11beta-disubstituted Estrogens: Probes for the Shape of the Ligand Binding Pocket in the Estrogen Receptor”; Bioorganic & Medicinal Chemistry Letters, Bd. 7, Nr. 22, (1997), pp. 2919-2924.
Anstead, G., M. ,et al., “The Estradiol Pharmacophore: Ligand Structure-Estrogen Receptor Binding Afinity Relationships and a Model for the Receptor Binding Site”; Steroids, Structure, Function, and Regulation, Bd. 62, Nr. 3, 1. (1997), pp. 268-303.
R. B. Gabbard, et al., “Structure Activity Relationships of Estrogens.” Effects of 14-Dehydrogenation and Axial Methyl Grops at c-7, c-9 and c-11; Steroids: Structure, Function, and Regulation, Bd. 41, Nr. 6, (1983), pp. 791-805.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

18 Norsteroids as selectively active estrogens does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with 18 Norsteroids as selectively active estrogens, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 18 Norsteroids as selectively active estrogens will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3437854

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.