Tetrahydroquinoline derivatives

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C514S311000, C514S314000

Reexamination Certificate

active

07858794

ABSTRACT:
The present invention relates to tetrahydroquinoline derivatives having gene formula (I) or a pharmaceutically acceptable salt thereof, wherein R1and R2are H or Me; R3is H, hydroxy, (1-4C)alkoxy, (di)(1-4C)alkylamino(2-4C)alkoxy or (2-6)heterocycloakl(2-4C)alkoxy; R4is H, OH, (1-4C)alkoxy or R7; R5is H, OH, (1-4C)alkoxy or R7, with the proviso that if R4is H, R5is not H, OH or (1-4C)alkoxy and that if R5is H, R4is not H, OH or (1-4C)alkoxy; R6is (2-5C)heteroaryl, (6C)aryl, (3-8C)cycloalkyl, (2 6C)heterocycloalkyl or (1-6C)alkyl; R7is amino, (di)(1-4C)alkylamino, (6C)arylcarbonylamino, (6C)arylcarbonyloxy, (2-5C) heteroarylcarbonylamino, (2-5C)heteroarylcarbonyloxy, R8-(2-4C)alkylamino, R8-(2-4C)alkoxy, R9-methylamino or R9-methoxy; R8is hydroxy, amino, (-14C)alkoxy, (di)(1-4C)alkylamino, (2-6C)heterocycloalkyl, (2-6C) heterocycloalkylcarbonylamino, (di)(1-4C)alkylaminocarbonylamino, (1-4C)alkoxycarbonylamino and R9is aminocarbonyl, (di)(1-4C)alkylaminocarbonyl, (2-5C)heteroaryl or (6C)aryl. The present invention also relates to pharmaceutical compositions comprising said derivatives and the use of these derivatives to regulate fertility.

REFERENCES:
patent: 2686182 (1954-08-01), Hopff et al.
patent: 6200963 (2001-03-01), Wrobel et al.
patent: 2004/0236109 (2004-11-01), Van Straten et al.
patent: 2006/0142334 (2006-01-01), Timmers
patent: 2006/0167047 (2006-07-01), Timmers et al.
patent: 0303 306 (1989-02-01), None
patent: WO 96/19458 (1996-06-01), None
patent: WO 00/08015 (2000-02-01), None
patent: WO 03/004028 (2003-01-01), None
The Chemistry of Heterocyclic compounds: Quinolines Part 1, Jones, Gurnos editor Wiley: New York, 1977 p. 104-117.
Nicole C. R. van Straten et. al. “Identification of Substituted 6-Amino-4-phenyltetrahydroquinoline Derivatives: Potent Antagonists for the Follicle-Stimulating Hormone Receptor” Journal of Medicinal Chemistry 2005, 48, 1697-1700.
M. Ram Sairam and Hanumanthappa Krishnamurthy “The Role of Follicle-Stimulating Hormone in Spermatogenesis: Lessons from Knockout Animal Models” Archives of Medical Research 32 (2001) 601-608.
Terry Kenakin and Ongun Onaran “The ligand paradox between affinity and efficacy: can you be there and not make a difference?” TRENDS in Pharmacological Sciences 2002, 23, 275-280.
Guo, Tao “Small molecule agonists and antagonists for the LH and FSH receptors.” Expert Opinion on Therapeutic Patents 2005 15(11) 1555-1564.
Dorwald F. A. Side Reactions in Organic Synthesis, 2005, Wiley: VCH, Weinheim p. IX of Preface p. 1-15.
Alfredo Ulloa-Aguirre et. al. “Role of the intracellular domains of the human FSH receptor in G□S protein coupling and receptor expression.” Molecular and Cellular Endocrinology 2007, 260-262, 153-162.
International Search Report, No. PCT/EP03/51025, Jun. 14, 2004.
Ronald L. Atkins et al., “Substituted Coumarins and Azacoumarins. Synthesis and Fluorescent Properties,” J. Org. Chem., vol. 43, No. 10, pp. 1975-1980 (1978).
Jay V. Johnson et al., “2,4-Diamino-5-benzylpyrimidines and Analogues as Antibacterial Agents. 12.1,2-Dihydroquinolymethyl Analogues with High Activity and Specificity for Bacterial Dihydrofolate Reductase,” J. Med. Chem. vol. 32, pp. 1942-1949 (1989).
James P. Edwards et al., “5-Aryl-1,2-dihydro-5H-chromeno[3,4-f]quinolines as Potent, Orally Active, Nonsteroidal Progesterone Receptor Agonists: The Effect of D-Ring Substituents,” J. Med. Chem. vol. 41, pp. 303-310 (1998).
Lawrence G. Hamann et al., “Synthesis and Biological Activity of a Novel Series of Nonsteroidal, Peripherally Selective Androgen Receptor Antagonists Derived from 1,2-Dihydrophyridono[5,6-g]quinolines,” J. Med. Chem, vol. 41, pp. 623-639 (1998).
Maria-Elena Theoclitou et al, “Novel facile synthesis of 2,2,4 substituted 1,2-dihydroquinolines via a modified Skraup reaction,” Tetrahedron Letters 43, pp. 3907-3910 (2002).
Jennifer H. Dorrington et al., “Effects of FSH on Gonadal Functions,” Recent Progress in Hormone Research, Vo. 35, pp. 301-342 (1979).
“Gonadotropin Therapy: New Trends and Insights,” Int J. Fertil, vol. 33, pp. 85-97 (1988).
Richard M. Sharpe “Intratesticular Control of Steroidogenesis,” Clinical Endocrinology, vol. 33, pp. 787-807 (1990).
Jane H. Morse et al., “Heterogeneity of Proteins in Commercial Preparations of Human Chorionic Gonadotropin (hCG) Demonstrated by Western Blotting,” American Journal of Reproductive Immunology and Microbiology, vol. 17 pp. 134-140 (1988).
Wiebe Olijive et al., “Molecular biology and biochemistry of human recombinant follicle stimulating hormone (Puregon®),” Molecular Human Reproduction, vol. 2, No. 5, pp. 371-382 (1996).
Daniel Navot et al., “The Use of Follicle-Stimulating Hormone for Controlled Ovarian Hyperstimulation in in Vitro Fertilization,” vol. 4, pp. 3-13 (1988).
“Successful in-vitro fertilisation and embryo transfer after treatment with recombinant human FSH,” The Lancet, vol. 339, pp. 1170-1171 (1992).
CAS 327981-38-4.
CAS 360760-14-1.
CAS 299418-67-0.
CAS 299970-20-0.
Chemical Abstracts, vol. 79, No. 9, Sep. 3, 1973, Columbux, Ohio, US; abstract No. 53152; Lugovik, B. A. et al: “Structure of compounds obtained from the interaction of 1, 2-dihydroquinolines with alkylbenzenes”.
Chemical Abstracts, vol. 77, No. 25, Dec. 18, 1972, Columbus, Ohio, US: abstract No. 164415, Lugovik, B.A.et al: “Reaction of 1, 2-dihydroqunolines with benzene and halobenzenes”.
Chemical Abstracts, vol. 105, No. 7, Aug. 18, 1986, Columbus, Ohio, US; abstract No. 56990, Shmyreva, Zh. V. et al: “Modification of anion exchanger Fuolite A 368 PR for the covalent immobilization of glucoamylase”.
Chemical Abstracts, “Ambinter Screening Collection”, May 31, 2001.
Chemical Abstracts, Columbus Ohio, “VITAS-M Screening Collection”, Mar. 22, 2001.
Atanes et. al., “Synthesis of 7-Substituted Dehydronoraporphines, with some Biogenetic Considerations,”Tetrahedron 50(1994) 11257-11266.
Barmettler et. al., “Acid-Catalyzed [3,3]-Sigmatropic Rearrangements ofN-Propargylanilines,”Helv. Chim. Acta 73(1990) 1515-1573.
Bonnat et. al., “The Solid Phase Synthesis of a Guanidinium Based ‘Tweezer’ Receptor,”Tetrahedron Lett. 37(1996) 5409-5412.
Bouyssou et. al., “Synthesis of 7- and 5,7-Substituted-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinolines: Convenient Precursors of Quinolone Antibacterial Agents,”J. Heterocycl. Chem. 29(1992) 895-898.
Cerfontain et al., “The Positional Reactivity Order in the Sulfur Trioxide Sulfonation of Benzene and Naphthalene Derivatives Containing an Electron-Withdrawing Substituent,”Recl. Trav. Chim. Pays-Bas, 113 (1994) 403-410.
Coppock, A., “New Synthesis of Aryl Esters of Aromatic Acids,”J. Org. Chem. 22(1957) 325-326.
Edwards et. al., “Lewis-acid Catalyzed Reaction of 2-1sopropenylaniline with Ketones: Improved Synthesis of 2,2,4-Trisubstituted 1,2-Dihydroquinolines,”Tetrahedron Lett. 39(1998) 5139-5142.
Hayler et. al., “The Design and Synthesis of Thrombin Inhibitors: The Introduction of In Vivo Efficacy and Oral Bioavailability into Benzthiazolylalanine Inhibitors,”Bioorg. Med. Chem. Lett. 10(2000) 1567-1570.
Jia et al., “Expression of Human Luteinizing Hormone (LH) Receptor: Interaction with LH and Chorionic Gonadotropin from Human but not Equine, Rat, and Ovine Species,”Mol. Endo. 5(1991) 759-768.
Knoevenagel, E., “Information on the Ketone Anils, I: Preparation of Aliphatic Ketone Anils and Alkaline Hydrolysis of Ketone Anil Iodoalkylates,” Ber. Dtsch. Chen. Gesellschaft 54 (1921) 1722-1730 (English-language translation attached.).
Lin et. al., “Substitution Reaction of Tetracyanoethylene with Acetone-Anils,”J. Chin. Chem. Soc. 43(1996) 497-501.
Lugovik et. al., Dokl. Akad. Nauk SSSR, 170:340

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

Tetrahydroquinoline derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Tetrahydroquinoline derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Tetrahydroquinoline derivatives will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-4165563

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