Modified, hydroxy-substituted aromatic structures having...

Organic compounds -- part of the class 532-570 series – Organic compounds – Cyclopentanohydrophenanthrene ring system containing

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C514S180000, C552S502000

Reexamination Certificate

active

06844456

ABSTRACT:
The present invention is directed to modified, hydroxy-bearing aromatic ring structures having cytoprotective activity. More specifically, in a first embodiment the present invention is directed to phenolic compounds, and in particular steriods (e.g., estrogens), wherein a non-fused polycyclic, hydrophobic substituent is attached to the hydroxy-substituted A-ring thereof. The present invention is further directed to a process for conferring cytoprotection to a population of cells involving the administration of the compound.

REFERENCES:
patent: 3472885 (1969-10-01), Bucourt et al.
patent: 4330540 (1982-05-01), Zeelen
patent: 4617298 (1986-10-01), Bodor et al.
patent: 4786647 (1988-11-01), Simpkins et al.
patent: 5552395 (1996-09-01), Gemmill, Jr. et al.
patent: 5554601 (1996-09-01), Simpkins et al.
patent: 5554604 (1996-09-01), Bonfils et al.
patent: 5679668 (1997-10-01), Bonfils et al.
patent: 5824672 (1998-10-01), Simpkins et al.
patent: 5843934 (1998-12-01), Simpkins
patent: 5859001 (1999-01-01), Simpkins et al.
patent: 5877169 (1999-03-01), Simpkins
patent: 5914325 (1999-06-01), Droescher et al.
patent: 5939407 (1999-08-01), Landfield
patent: 5972923 (1999-10-01), Simpkins et al.
patent: 6080735 (2000-06-01), Schwartz et al.
patent: 6172056 (2001-01-01), Droescher et al.
patent: 6197833 (2001-03-01), Simpkins et al.
patent: 6207658 (2001-03-01), Simpkins et al.
patent: 6245756 (2001-06-01), Patchev et al.
patent: 6265147 (2001-07-01), Mobley et al.
patent: 6436917 (2002-08-01), Droescher et al.
patent: 1 167 837 (1984-05-01), None
patent: 199 17 930 (2000-10-01), None
patent: 0 069 424 (1983-01-01), None
patent: 1 298 587 (1972-12-01), None
patent: WO 9513076 (1995-05-01), None
patent: WO 9703661 (1997-02-01), None
patent: WO 9926630 (1999-06-01), None
patent: WO 0063228 (2000-10-01), None
patent: WO 0110430 (2001-02-01), None
P.S. Green et al. “ENT-Estradiol Exerts Neuroprotective Effects in vitro and in vivo” Society for Neuroscience Abstracts, vol. 25, No. 1/2 (Oct. 23, 1999) p. 1849.
C. Behl et al. “Neuroprotection against oxidative stress by estrogens: structure-activity relationship” Molecular Pharmacology, vol. 51, No. 4 (1997) pp. 535-541.
Ismail et al. “Synthesis and Biological Evaluation of Some Novel 2-(pyrimidin-4-yl)estradiol Derivatives” Eur. J. Med. Chem., vol. 30, No. 5 (1995) pp. 423-427.
Omar et al. “Synthesis, Binding Affinities and Uterotrophic Activity of Some 2-Substituted Estradiol and Ring-A-Fused Pyrone Derivatives” Eur. J. Med. Chem., vol. 29, No. 1 (1994) pp. 25-32.
Akhter et al., Saftey Study of Tirilazad Mesylate in Patients With Acute Ischmeic Stroke (STIPAS) Stroke, vol. 25, No. 2 (1994) p. 418-423.
A. Allais et al. “3-(β-Dialkylaminoethoxy)estra-1,3,5(10)-trienes” Chemical Abstracts, vol. 70, No. 25; Abstract No. 115418e (1969) p. 381.
K. Barnikol-Oettler et al. “Preparation of Estradiol 3-methyl Ether” Chemical Abstracts, vol. 160, No. 25, Abstract No. 106:214199c (1987).
C. Behl et al. “17-βEstradiol Protects Neurons from Oxidative Stress-Induced Cell Death in vitro” Biochemical and Biophysical Research Communications, vol. 216, No. 2 (1995) pp. 473-482.
G.C. Buzby et al. “Totally Synthetic Steriod Hormones. XIII. The Chemical Resolution of Some Racemic Estrane, 13β-Ethylgonane, and 13β-n-Propylgonane Derivatives and the Preparation of Some Estrane and 13β-Ethylgonne Derivatives of Unnatural Configuration” Journal of Medicinal Chemistry, vol. 10 (1967) pp. 199-204.
T. Fan et al. “ZYC-13, the enantiomer of 1,3,5(10)-estratriene 3-OL, exerts neuroprotective effects in vitro and in vivo” Presented at the 26th Soc. for Neuroscience Meeting, Nov. 4, 2000 to Nov. 9, 2000.
Y. Goodman et al. “Estrogens Attenuate and Corticosterone Exacerbates Excitotoxicity, Oxidative Injury, and Amyloid β-Peptide Toxicity in Hippocampal Neurons” Journal of Neurochemistry, vol. 66, No. 5 (1996) pp. 1836-1844.
P. Green et al. “The Nonfeminizing Enantiomer of 17β-Estradiol Protective Effects in Neuronal Cultures and a Rat Model of Cerebral Ischemia” Endocrinology, vol. 142, No. 1 (2001) pp. 400-406.
Hall et al. “Sex Differences in Postischemic Neuronal Necrosis in Gerbils” j. Cer. Blood Flow Metab., vol. 11 (1991) p. 292-298.
H. Kaneko et al. “The Synthesis of 2- and 4-Alkoxymethylestrogenes” Chem. Pharm. Bull., vol. 12, No. 2 (1964) pp. 196-203.
M. A. Levitt et al. “Reduction of Infarct Size During Myocardial Ischemia and Reperfusion by Lazaroid U-74500A, a Nonglucocorticoid 21-Aminosteriod” J. of Cardiovascular Pharmacology, vol. 23, No. 1 (1994) pp. 136-140.
W. Lunn et al. “The Adamantyl Carbonium Ion as a Dehydrogenating Agent, its Reactions with Estrone” Tetrahedron Letters, vol. 24, No. 23 (1968) pp. 6773-6776.
C. Miller et al. “In vitro antioxidant effects of estrogens with a hindered 3-OH function on the copper-induced oxidation of low density lipoprotein” Steroids, vol. 61 (1996) pp. 305-308.
Mooradian “Antioxidant Properties of Steroids” J. Steroid Boichem. Molec. Biol., vol. 45, No. 6 (1993) pp. 509-511.
M. Nakano et al. “Novel and Potent Biological Antioxidants on Membrane Phospholipid Peroxidation: 2-Hydroxy Estrone and 2-Hydrox Estradiol” Bochemical and Biophycial Research Communications, vol. 142, No. 3 (1987) pp. 919-924.
E. Niki et al. “Antioxidants in Relation to Lipid Peroxidation” Chemistry and Physics of Lipids, vol. 44, Nos. 2-4 (1987) pp. 227-253.
T. Patton et al. “Estrogens. IV. The Synthesis of 2- and 4-Alkylestrones” Journal of Organic Chemistry, vol. 27, No. 3 (1962) pp. 910-914.
E. J. Perez et al. “762.7—Structure-Activity Relationship of Estratrienes Against Glutamate Toxicity in a Mouse Hippocampal Cell Line” Presented at the 26th Soc. for Neuroscience Meeting, Nov. 4, 2000 to Nov. 9, 2000.
L. Prokai et al. “Synthesis and Biological Evaluation of 17β-Alkoxyestra-1,3,5(10)-trienes as Potential Neuroprotectants Against Oxidative Stress” J. Med. Chem., vol. 44, No. 1 (2001) pp. 110-114.
W. Romer et al. “Novel estrogens and their radical scavenging effects, iron-chelating, and total antioxidative actives: 17α-substituted analogs of Δ9(11)-dehydro-17β-estradiol” Steroids, vol. 62 (1997) pp. 688-694.
W. Romer et al. “Novel “scavestrogens” and their radical scavenging effects, iron-chelating, and total antioxidative actives: Δ8,9-dehydro derivatives of 17-α-estradiol and 17β-estradiol” Steroids, vol. 62 (1997) pp. 304-310.
A.G. Schering, “Preparation of ent-steroids as Selectively Effective Estrogens” Chemical Abstracts, vol. 133, No. 21, Abstract No. 133:296594x (2000) p. 766-767.
A. Seelig et al. “A method to determine the ability of drugs to diffuse through the blood-brain barrier” Proc. Natl. Acad. Sci. USA, vol. 91 (1994) pp. 68-72.
L. Tietze et al. “Synthesis of new 16-spirosteroids” Steroids, vol. 59 (1994) pp. 305-309.
J. Wilson et al. “U83836E Reduces Secondary Brain Injury in a Rabbit Model of Cryogenic Trauma” Journal of Trauma, vol. 39, No. 3 (1995) pp. 473-479.
A. Wunderli et al. “Geometry of the Activated Complex of the Thermal and Charge-Induced Aromatic Para to Ortho Claisen Rearrangement” Helvetica Chimica Acta, vol. 56 (1973) pp. 989-1011.
S. Xia et al. “A Novel Estrogen Analog, Inactive at the Estrogen Receptor, is Neuroprotective” Presented at the 26th Soc. for Neuroscience Meeting, Nov. 4, 2000 to Nov. 9, 2000.
S-H. Yang et al. “Neuroprotective Effects of a Novel Non-Recptor Binding Estrogen Analogue During Stroke” Presented at the 26th Soc. for Neuroscience Meeting, Nov. 4, 2000 to Nov. 9, 2000.

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

Modified, hydroxy-substituted aromatic structures having... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Modified, hydroxy-substituted aromatic structures having..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Modified, hydroxy-substituted aromatic structures having... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3378678

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