Tricyclic androgen receptor modulator compounds and methods

This invention relates to non-steroidal tricyclic compounds that are modulators of androgen receptors and to methods for making and using such compounds.

Saved in:
Bibliographic Details
Main Authors Zhi, Lin, Van Oeveren, Cornelis Arjan
Format Patent
LanguageEnglish
Published 01.06.2010
Online AccessGet full text

Cover

Abstract This invention relates to non-steroidal tricyclic compounds that are modulators of androgen receptors and to methods for making and using such compounds.
AbstractList This invention relates to non-steroidal tricyclic compounds that are modulators of androgen receptors and to methods for making and using such compounds.
Author Van Oeveren, Cornelis Arjan
Zhi, Lin
Author_xml – sequence: 1
  givenname: Lin
  surname: Zhi
  fullname: Zhi, Lin
– sequence: 2
  givenname: Cornelis Arjan
  surname: Van Oeveren
  fullname: Van Oeveren, Cornelis Arjan
BookMark eNrjYmDJy89L5WSwDinKTK5MzslMVkjMSynKT0_NUyhKTU4tKMkvUsjNTynNSQSxkvNzC_JL81KKQaoUclNLMvJTinkYWNMSc4pTeaE0N4OCm2uIs4duaXFBYklqXklxfHpRIogyMDc3Mre0MDAmQgkA0xAyzA
ContentType Patent
CorporateAuthor Ligand Pharmaceuticals Incorporated
CorporateAuthor_xml – name: Ligand Pharmaceuticals Incorporated
DBID EFH
DatabaseName USPTO Issued Patents
DatabaseTitleList
Database_xml – sequence: 1
  dbid: EFH
  name: USPTO Issued Patents
  url: http://www.uspto.gov/patft/index.html
  sourceTypes: Open Access Repository
DeliveryMethod fulltext_linktorsrc
ExternalDocumentID 07727980
GroupedDBID EFH
ID FETCH-uspatents_grants_077279803
IEDL.DBID EFH
IngestDate Sun Mar 05 22:33:04 EST 2023
IsOpenAccess true
IsPeerReviewed false
IsScholarly false
Language English
LinkModel DirectLink
MergedId FETCHMERGED-uspatents_grants_077279803
OpenAccessLink https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7727980
ParticipantIDs uspatents_grants_07727980
PatentNumber 7727980
PublicationCentury 2000
PublicationDate 20100601
PublicationDateYYYYMMDD 2010-06-01
PublicationDate_xml – month: 06
  year: 2010
  text: 20100601
  day: 01
PublicationDecade 2010
PublicationYear 2010
References Derwent citing Russian patent, SU 241441 published Apr. 1969, for: "Methyl beta-aminoethyl pyrrolo quinoline prodn.-by reacting hydrazino-quinoline with methyl-chloropropyl ketone in alcohol."
(96/19458) 19960600
Tan, Skin Therapy Letter, vol. 6, num 5, pp. 1-8, 2001.
Edwards, et al., "Preparation, resolution, and biological evaluation of 5-aryl-1,2-dihydro-5H-chromeno[3,4-f]quinolines potent, orally active, nonsteroidalprogesterone receptor agonists," J Med Chem., 41(15)2779-85.(1998).
Bolognese et al., "Photochemistry of Ommochromes and Related Compounds," J. Heterocyclic Chem. 25: 979-983 (1988).
(2 126 811) 19721200
Bolognese et al., "Oxidation of 3-Hydroxykynurenine. A Reexamination," J. Heterocyclic Chem. 25: 1247-1250 (1988).
Zhi et al., "Development of progesterone receptor antagonist from 1,2-dihydrochromeno [3,4-f]quinoline agonist pharmacophore," Bioorg. Med. Chem. Lett. 13(12):2075-2078 (2003).
Jones et al. (5696130) 19971200
Shirota et al., "Antiandrogenic natural Diels-Alder-type adducts from Brosimum rubescens," J. Nat. Prod. 60(10):997-1002 (1997).
Lancelot et al., "Pyrido[2,3-h]pyrrolo[1,2-α]quinoxalines," Chem. Pharm. Bull. 31: 3160-3167 (1983) [Article in French, English abstract on first page of article].
Higuchi, et al., "4-Alkyl- and 3,4-dialkyl-1,2,3,4-tetrahydro-8-pyridono[5,6-g]quinolinespotent, nonsteroidal androgen receptor agonists," Bioorg Med Chem Lett., 9(9):1335-40.(1999).
Ohta, "Juvenile Hormone Antagonists," Kagakuto Seibufsu, 17(2): 92-94 (1979).
Rosen, et al., "Intracellular receptors and signal transducers and activators of transcriptionsuperfamilies novel targets for small-molecule drug discovery," J Med Chem., 38(25):4855-74. (1995).
Willard et al. , "Potential Diuretic-β-Adrenergic Blocking Agents: Synthesis of 3-[2-[1,1-Dimethylethyl)amino]-1-hydroxyethyl]-1,4-dioxino[2,3-g]quinolines," J.Org. Chem. 46: 3846-3852 (1981).
Yamashkin et al., "Reactivities of 5-, 6-, and 7-(enamino)indoles in the synthesis of pyrroloquinolines," Chem. Heterocyc. Cmpd. (Translation of Khim. Geterotsikl. Soedin.) 34(9):1050-1065 (1998).
Coghlan et al. (6380207) 20020400
Jones et al. (5688808) 19971100
Zhi et al. (7071205) 20060700
Zhi, et al., "5-Aryl-1,2-dihydrochromeno[3,4-f]quinolines a novel class of nonsteroidalhuman progesterone receptor agonists," J Med Chem., 41(3):291-302. (1998).
Poot et al. (3928686) 19751200
(07-013017) 19950100
Liska, CA 74:41539, abstract only of Tet Letters, vol. 53, pp. 4657-4660, 1970.
Zouboulis, dermatology, vol. 206, pp. 37-53, 2003.
Walsh, et al., "Inhibition of extratesticular stimuli to prostatic growth in the castrated rat by antiandrogens," Endrocrinology 86: 624 (1970).
(WO 00/31081) 20000600
Edwards et al. (6534516) 20030300
Zhi et al. (2004/0152717) 20040800
Negro-Vilar, "Selective androgen receptor modulators (SARMs) a novel approach to androgentherapy for the new millennium," .J Clin Endocrinol Metab., 84(10)3459-62. (1999).
Hayatsu et al. (4623638) 19861100
(2004/033460) 20040400
Ishii et al., "Formation of Hydroxanthommatin-Derived Radical in the Oxidation of 3-Hydroxykynurenine," Archives of Biochemistry and Biophysics 294(2): 616-622 (1992).
Zhi et al., "5-Alkyl 1,2-dihydrochromeno[3,4-f]quinolines: a novel class of nonsteroidal progesterone receptor modulators," Bioorg. Med. Chem. Lett. 8(23):3365-3370 (1998).
Dalton et al. (6569896) 20030500
(99/58486) 19991100
Mcllroy, et al., "Effects of Proteinase Inhibitors on Adenylate Cyclase," Biochem. J., 188: 423-435 (1980).
Jones et al. (6093821) 20000700
Morgan, CA 26:41810, abstract only of J of Chem Soc, pp. 1910-1912, 1932.
(2005/090282) 20050900
Certified English translation of: Ohta, "Juvenile Hormone Antagonists," Kagakuto Seibufsu, 17(2): 92-94 (1979).
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., 41(3)303-10 (1998).
Hayatsu et al. (4460475) 19840700
Yoshikawa T., "Synthesis of 4,6-diaminoquinoline derivatives. I. Synthesis of pyrrolo (f) quinoline derivatives," Yakugaku Zasshi (1961)81: 1317-22 (Abstract).
Edwards et al. (6180794) 20010100
Akhvlediani et al., "Chichibabin reaction in a series of angular pyrroloquinolines," Zhurnal Organicheskoi Khimii (1981), 17(7), 1542-6. (Chemical Abstract).
Edwards, J., et al., "Nonsteroidal Androgen Receptor Agonists Based on 4-(Trifluoromethyl)-2H-Pyrano[3,2-g]Quinolin-2-One," Biooreanic & Medicinal Chemistrv Letters, 9: 1003-1008 (1999).
Fujisaki, S., et al., "Halogenation Using N-Halogenocompounds. I. Effect of Amines on ortho Bromination of Phenols with NBS," Bull. Chem.Soc. Jpn., 66: 1576-1579 (1993).
Jones et al. (5688810) 19971100
(96/20914) 19960700
Daniell, abstract only of J of Urology, vol. 163, Issue 1, pp. 181-186, Jan. 2000.
Robaire, Bio of Reporduction, vol. 31, pp. 221-230, 1984.
Higuchi et al. (2002/0183314) 20021200
Castillo, P. and J.C. Rodriguez-Ubis, "A high-yield method for the methylenation of o-dihydroxyaromatic compounds: synthesis of methylenedioxycoumarins," Synthesis pp. 839-840 (1986).
Kawamori et al., "Effects of heterocyclic amines with mammary gland carcinogenic potential on estrogenic response of uterus in ovariectomized rats," Cancer Letters 162: 31-37 (2001).
Jones et al. (6696459) 20040200
Chemical Abstracts vol. 131, No. 213835, (1999) for: [Yamashkin et al. Chemistry of Heterocyclic Compounds (New York)(Translation of Khimiya Geterotsiklicheskikh Soedinenii) (1999), Volume Date 1998, 34(9), 1050-1065.]
(2004/033461) 20040400
Yin, et al., "Key structural features of nonsteroidal ligands for binding and activation of the androgen receptor," Molecular Pharmacology, 63 (1), 211-223 (2003).
(2005/018573) 20050300
Dey, CA 21:3199, abstract only of Quart j Indian Chem Soc, vol. 3, pp. 166-176, 1926.
(2009/082437) 20090700
Hamann, L., et al., "Synthesis and Biological Activity of a Novel Series of Nonsteroidal, Peripherally Selective Androgen Receptor Antagonists Derived from I ,2-Dihydropyridono[5,6-glquinolines," J. Med. A, Chem 41: 623-639 (1998).
Higuchi, R., et al., "4-Alkyl-and 3,4-Dialkyl-1,2,3,4-Tetrahydro-8-Pyridono[5,6-g]Quinolines: Potent, Nonsteroidal Androgen Receptor Agonists,"Bioorganic&Medicinal Chemistrv Letters, 9: 1335-1340 (1999).
Luke, et al., "The Male Sex Accessory Tissues; Structure, Androgen Action, and Physiology," The Physiology of Reproduction, 1435-1487 (1994).
(97/49709) 19971200
Lawson, et al., "Androgen responsiveness of the pituitary gonadotrope cell line LbetaT2," J Endocrinol., 170(3)601-7.(2001).
Rosen and Negro-Vilar, "Novel, non-steroidal, selective androgen receptor modulators (SARMs) with anabolic activity in bone and muscle and improved safety profile," Journal of Musculoskeletal Neuronal Interactions, 2(3):222-224 (2002).
Yudin LG et al., "Nitropyrroloquinolines," Khimiya Geterotsikicheskikh Soedinenii (1979)10: 1381-5.
(94/23068) 19941000
Berger et al., "Interaction of glucocorticoid analogues with the human glucocorticoid receptor," J. Steroid Biochemistry and Molecular Biology 41(3-8): 733-738 (1992).
(548608) 19770200
Evans et al. (4981784) 19910100
Coghlan et al. (6506766) 20030100
(03-282445) 19911200
Zhi, et al., "Switching androgen receptor antagonists to agonists by modifying C-ringsubstituents on piperidino[3,2-g]quinolinone," Bioorg Med Chem Lett., 9(7):1009-12. (1999).
Gross (5179202) 19930100
(50-25595) 19750300
Miner and Tyree, "Drug discovery and the intracellular receptor family," Vitam Horm., 62:253-80. (2001).
Mustafa et al., "Photochemical reaction in sunlight. Experiments with benzo[k]quinoline-5,6-quinone, monoamine and monoxmine derivatives in sunlight and in dark," J. A. Chem. Soc. 81:3409-3413 (1959).
(2003-520231) 20030700
Schimitschek et al., "New laser dyes with blue-green emission," Opt. Commun. 16:313-316 (1976).
Certified English Translation of German patent DE 2 126 811, published Dec. 14, 1972, entitled "Flourescent pigments dyes-of the coumarin series for synthetic fibres and plastics,". Inventor: Scheuerrmann. [27 pages].
(2004/033459) 20040400
Singh, Curr Med Chem, VOI 7, pp. 211-247, 2000.
Sperry, et al., "Farnesol oxidation in insects: evidence that the biosynthesis of insect juvenile hormone is mediated by a specific alcohol oxidase," Insect Biochem. Mol. Biol., 31(2): 171-178(2001).
(50-19777) 19750300
Singh et al., "Androgen receptor antagonists (antiandrogens): structure-activity relationships," Curr. Med. Chem. 7(2): 211-247 (2000).
(02/066475) 20020800
(2427409) 19750100
Claman et al., "SOGC clinical practice guidelines. Hirsutism: evaluation and treatment," J Obstet Gynaecol Can. 24(1):62-7 (2002).
(89/07441) 19890800
LaMontagne et al., "Antimalarials. 13. 5-Alkoxy Analogues of 4-Methylprimaquine," J. Med. Chem. 25: 964-968 (1982).
Zhi, L. and Martinborough, E. Chapter 17. Selective androgen receptor modulators (SARMs) Annual Reports in Medicinal Chemistry, vol. 36:169-180 (2001).
Jones et al. (6448405) 20020900
Jones et al. (5011697) 19910400
(WO 90/08529) 19900800
Meriggiola, J of andrology, vol. 24, vol. 4, pp. 466-483, 2003.
Simenthal et al., "Transcriptional Activation and Nuclear Targeting Signals of the Human Androgen Receptor," The Journal of Biological Chemistry 266(1): 510-518 (1991).
Jones et al. (6121450) 20000900
Zhi, et al., "5-Aryl-1,2,3,4-tetrahydrochromeno[3,4-f]quinolin-3-ones as a novel class ofnonsteroidal progesterone receptor agonists effect of A-ring modification," .J Med Chem., 42(8):1466-72.(1999).
Jones, G., Comprehensive Heterocyclic Chemistry, Katritzky, A.R.; Rees, C.W., eds. Pergamon, New York, 1984, vol. 2, Chap. 2.08, pp. 421-426.
Zhi et al. (6964973) 20051100
(01/16133) 20010300
Chapman NB et al., "Some substitution reactions of thieno[3,2-f]quinoline," Journal of the Chemical Society (Section)C: Organic (1970)17: 2334-9.
Chemical Abstracts vol. 110, No. 75273 (1989) [Gryanznov AP., "Reactivity of 1H-pyrrolo [2.3-f]-3H-pyrrolo[3.2-f] quinolines and their derivatives," lzvestiya Timiryazevskoi Sel 'skokhozyaistvennoi Akademii, 3: 185-90 (1988)].
Jones et al. (5693646) 199
References_xml – year: 19961200
  ident: 96/41013
– year: 20000700
  ident: 6093821
  contributor:
    fullname: Jones et al.
– year: 20030300
  ident: 6534516
  contributor:
    fullname: Edwards et al.
– year: 19911200
  ident: 5071773
  contributor:
    fullname: Evans et al.
– year: 20020300
  ident: 6358948
  contributor:
    fullname: Zhang et al.
– year: 20020700
  ident: 2002/0094983
  contributor:
    fullname: Zhang et al.
– year: 20040200
  ident: 6696459
  contributor:
    fullname: Jones et al.
– year: 19930100
  ident: 5179202
  contributor:
    fullname: Gross
– year: 19690400
  ident: 241441
– year: 19971200
  ident: 2259031
– year: 19971200
  ident: 5693646
  contributor:
    fullname: Jones et al.
– year: 19960600
  ident: 96/19458
– year: 19861100
  ident: 4623638
  contributor:
    fullname: Hayatsu et al.
– year: 19960700
  ident: 96/20914
– year: 20040600
  ident: 2004/045518
– year: 20000200
  ident: 6030967
  contributor:
    fullname: Marui et al.
– year: 19971100
  ident: 5688808
  contributor:
    fullname: Jones et al.
– year: 20000100
  ident: 6017924
  contributor:
    fullname: Edwards et al.
– year: 19750300
  ident: 50-25595
– year: 20010300
  ident: 01/16139
– year: 19961100
  ident: 5576324
  contributor:
    fullname: Kyotani et al.
– year: 20020900
  ident: 02/068427
– year: 19910100
  ident: 4981784
  contributor:
    fullname: Evans et al.
– year: 19971000
  ident: 5677336
  contributor:
    fullname: Jones et al.
– year: 20040800
  ident: 2004/0152717
  contributor:
    fullname: Zhi et al.
– year: 20051200
  ident: 2005/0288350
  contributor:
    fullname: Zhi et al.
– year: 19750300
  ident: 50-19777
– year: 19941000
  ident: 94/23068
– year: 20040400
  ident: 2004/033460
– year: 20030500
  ident: 6569896
  contributor:
    fullname: Dalton et al.
– year: 20021000
  ident: 6462038
  contributor:
    fullname: Higuchi et al.
– year: 20020400
  ident: 6380207
  contributor:
    fullname: Coghlan et al.
– year: 19971200
  ident: 5696127
  contributor:
    fullname: Jones et al.
– year: 19991100
  ident: 5994544
  contributor:
    fullname: Jones et al.
– year: 20051100
  ident: 6964973
  contributor:
    fullname: Zhi et al.
– year: 20050900
  ident: 2005/090282
– year: 20030800
  ident: 2003/0149268
  contributor:
    fullname: Hamann et al.
– year: 20021200
  ident: 2002/0183346
  contributor:
    fullname: Zhi et al.
– year: 20020800
  ident: 02/066475
– year: 20050300
  ident: 2005/018573
– year: 19950100
  ident: 07-013017
– year: 19890800
  ident: 89/07441
– year: 20040400
  ident: 2004/033459
– year: 20030500
  ident: 6566372
  contributor:
    fullname: Zhi et al.
– year: 20030300
  ident: 2003/0055094
  contributor:
    fullname: Sun et al.
– year: 19971200
  ident: 5696130
  contributor:
    fullname: Jones et al.
– year: 19910400
  ident: 5011697
  contributor:
    fullname: Jones et al.
– year: 20040400
  ident: 2004/033461
– year: 19990800
  ident: 0933350
– year: 20000900
  ident: 6121450
  contributor:
    fullname: Jones et al.
– year: 20010700
  ident: WO 01/52841
– year: 19971200
  ident: 5696133
  contributor:
    fullname: Jones et al.
– year: 20030100
  ident: 6506766
  contributor:
    fullname: Coghlan et al.
– year: 20000600
  ident: WO 00/31081
– year: 19881000
  ident: 4777052
  contributor:
    fullname: Weisburger et al.
– year: 19930400
  ident: 0638571
– year: 19770200
  ident: 548608
– year: 19970400
  ident: 97/12853
– year: 20020100
  ident: 6340704
  contributor:
    fullname: Marui et al.
– year: 19911200
  ident: 03-282445
– year: 19751200
  ident: 3928686
  contributor:
    fullname: Poot et al.
– year: 20010100
  ident: 6180794
  contributor:
    fullname: Edwards et al.
– year: 20060700
  ident: 7071205
  contributor:
    fullname: Zhi et al.
– year: 20010300
  ident: 01/16133
– year: 20030700
  ident: 2003-520231
– year: 20031200
  ident: 6667313
  contributor:
    fullname: Hanmann et al.
– year: 19721200
  ident: 2 126 811
– year: 19961100
  ident: 96/36230
– year: 20040700
  ident: 2004/0147530
  contributor:
    fullname: Zhi et al.
– year: 19750100
  ident: 2427409
– year: 20070500
  ident: 7214690
  contributor:
    fullname: Higuchi et al.
– year: 19900800
  ident: WO 90/08529
– year: 19971100
  ident: 5688810
  contributor:
    fullname: Jones et al.
– year: 19990200
  ident: 11-29471
– year: 20040900
  ident: 2004/0186132
  contributor:
    fullname: Jones et al.
– year: 20000500
  ident: 3047434
– year: 20020900
  ident: 6448405
  contributor:
    fullname: Jones et al.
– year: 20010300
  ident: 01/16108
– year: 19971200
  ident: 5693647
  contributor:
    fullname: Jones et al.
– year: 19751100
  ident: 3919238
  contributor:
    fullname: Spencer et al.
– year: 20090700
  ident: 2009/082437
– year: 20021200
  ident: 2002/0183314
  contributor:
    fullname: Higuchi et al.
– year: 19840700
  ident: 4460475
  contributor:
    fullname: Hayatsu et al.
– year: 19991100
  ident: 99/58486
– year: 20000300
  ident: 00/12502
– year: 19971200
  ident: 97/49709
– year: 20031000
  ident: 2003/0186970
  contributor:
    fullname: Higuchi et al.
Score 2.771472
Snippet This invention relates to non-steroidal tricyclic compounds that are modulators of androgen receptors and to methods for making and using such compounds.
SourceID uspatents
SourceType Open Access Repository
Title Tricyclic androgen receptor modulator compounds and methods
URI https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7727980
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV3PS8MwFH7MIagnRcX5ixy8RmObdgk7jpUiKDtM2G2kTeLFtaPpGP73vtfK8KK3kISXkEde3ku-fA_gwcvYFhgpc6Lu5TIVlqtUaq6iceoT-axMB8Z8fUvzd_myTJYDyPd_Yda4jfgG5xIet2HT1h24Es17r3jekz8TR2BF7AO76rM2dm79E3qJY60weD9QgqB9syw_gSMUgS5b1YZfh0Z2CofzrvYMBq46h8kCTc5XiXKZIZYA1BxDc-Nw9Iata0t5tLBEGG9KdRSoF-sTPIcLYNlsMc35fqTVR0MIlpX4mVF8CUOM5N0VMF3q0hurvU6EtLHTXkaFiZzXJboNIhnB6E8x1_-03cBx_6hNlwO3MGybrbvDs7It7ruF-AZSB3Xt
link.rule.ids 230,309,783,805,888,64367
linkProvider USPTO
linkToPdf http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV1LT8QgEJ5sVuPjpFHj-uTgFa0tZUs8qk19bXpYk701tIAXt92Ubjb-ewdqNl70RoDMECbMA4ZvAK4Mi1SJkTJ10L2U8UDRhDNBk3DMTcxuE-mTMd8mPHtnz7N4NoBs_RdmjseILnAt9nppF13jkytRvfeCpz34s8MIrB36wKr-bKTKlblBL3EsEgzeN9DGch-SpdkubCMRdNrqzv4yG-kebOa-dx8Guj6Auykqna8KKRPpcAJQdgQVjkb-LZk3ylXSwpbL8nbFjqybRfoSz_YQSPo4vc_omlPx0bocliL4WVN0BEOM5fUxEFGJykgljIgDpiItDAtLGWojKnQcgngEoz_JnPwzdglb-UNavD5NXk5hp3_hdjcFZzDs2qU-R8PZlRd-T74BRdt46g
openUrl ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Apatent&rft.title=Tricyclic+androgen+receptor+modulator+compounds+and+methods&rft.inventor=Zhi%2C+Lin&rft.inventor=Van+Oeveren%2C+Cornelis+Arjan&rft.number=7727980&rft.date=2010-06-01&rft.externalDBID=n%2Fa&rft.externalDocID=07727980