The Substituent On The Ring Nitrogen Of The Five-membered Hetero Ring Contains A Bicyclo Carbocyclic Ring System Patents (Class 548/576)
  • Patent number: 10399939
    Abstract: Described herein are tetrahydronaphthalene compounds with estrogen receptor modulation activity or function having the Formula I structure: and stereoisomers, tautomers, or pharmaceutically acceptable salts thereof, and with the substituents and structural features described herein. Also described are pharmaceutical compositions and medicaments that include the Formula I compounds, as well as methods of using such estrogen receptor modulators, alone and in combination with other therapeutic agents, for treating diseases or conditions that are mediated or dependent upon estrogen receptors.
    Type: Grant
    Filed: November 8, 2016
    Date of Patent: September 3, 2019
    Assignee: Genentech, Inc.
    Inventors: Jun Liang, Daniel Fred Ortwine, Xiaojing Wang, Jason Zbieg
  • Patent number: 8937188
    Abstract: A solid crystalline form of 1-(2-[4-(6-methoxy-3,4-dihydronaphthalene-1-y) phenoxy]ethyl)pyrrolidine, and a preparing process thereof are provided. The aforesaid compound is a key intermediate in the synthesis of lasofoxifene. A process for preparing lasofoxifene, a process for purifying lasofoxifene tartrate, and a crystalline form of lasofoxifene tartrate are also provided.
    Type: Grant
    Filed: April 27, 2010
    Date of Patent: January 20, 2015
    Assignee: Glenmark Generics Ltd.
    Inventors: Mubeen Ahmed Khan, Nikhil Rasiklal Trivedi, Nagan Nirmalan Kandasamy, Dayaghan Gangadhar Patil, Vipin Kumar Pandey, Sukumar Sinha
  • Publication number: 20130137746
    Abstract: Described herein are compounds that are estrogen receptor modulators. Also described are pharmaceutical compositions and medicaments that include the compounds described herein, as well as methods of using such estrogen receptor modulators, alone and in combination with other compounds, for treating diseases or conditions that are mediated or dependent upon estrogen receptors.
    Type: Application
    Filed: June 15, 2011
    Publication date: May 30, 2013
    Applicant: ARAGON PHARMACEUTICALS, INC.
    Inventors: Steven P. Govek, Nicholas D. Smith
  • Publication number: 20120045648
    Abstract: A solid crystalline form of 1-(2-[4-(6-methoxy-3,4-dihydronaphthalene-1-y) phenoxy]ethyl)pyrrolidine, and a preparing process thereof are provided. The aforesaid compound is a key intermediate in the synthesis of lasofoxifene. A process for preparing lasofoxifene, a process for purifying lasofoxifene tartrate, and a crystalline form of lasofoxifene tartrate are also provided.
    Type: Application
    Filed: April 27, 2010
    Publication date: February 23, 2012
    Applicant: GLENMARK GENERRICS LTD
    Inventors: Mubeen Ahmed Khan, Nikhil Rasiklal Trivedi, Nagan Nirmalan Kandasamy, Dayaghan Gangadhar Patil, Vipin Kumar Pandey
  • Publication number: 20110009439
    Abstract: Compounds of formula (Ia): wherein R1, R2, R3, R4a, R4b, R5, and R6 are defined herein, as well as other indene derivatives are disclosed herein. Pharmaceutical compositions containing the compounds and methods of using the compounds are also disclosed.
    Type: Application
    Filed: February 23, 2010
    Publication date: January 13, 2011
    Applicant: AQUINOX PHARMACEUTICALS INC.
    Inventors: Jeffery R. Raymond, Kang Han, Yuanlin Zhou, Yuehua He, Bradley Noren, James Gee Ken Yee
  • Publication number: 20100317712
    Abstract: Compounds of this formula are useful for preventing breast cancer.
    Type: Application
    Filed: August 20, 2010
    Publication date: December 16, 2010
    Inventors: Kimberly O. Cameron, Paul A. Dasilva-Jardine, Hua Zhu Ke, Robert L. Rosati
  • Publication number: 20100256394
    Abstract: A method of preparing (?)-cis-(5R,6S)-6-phenyl-5-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-5,6,7,8-tetrahydronaphthalen-2-ol D-tartrate-lasofoxifene of formula 1, comprising the following steps a) Preparation of cis-1-{2-[4-(2-phenyl-6-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-phenoxy]ethyl}pyrrolidine of formula (3) by alkylation of cis-1-(4-hydroxyphenyl)-2-phenyl-6-methoxy-1,2,3,4-tetrahydronaphthalene with 1-(2-chloroethyl)pyrrolidine base or its salt, b) Deprotection of the hydroxyl group in the substance of formula (3) by the effect of hydrobromic acid generating cis-6-phenyl-5-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-5,6,7,8-tetrahydronaphthalen-2-ol hydrobromide of formula (2a), c) Conversion of the substance of formula (2a) into cis-6-phenyl-5-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-5,6,7,8-tetrahydronaphthalen-2-ol of formula (2b), d) Preparation of lasofoxifene of formula (1) by conversion into the corresponding diasteroisomer by reaction with D-tartaric acid and crystallization.
    Type: Application
    Filed: May 28, 2008
    Publication date: October 7, 2010
    Inventors: Petr Lustig, Ludmila Hejtmankova
  • Publication number: 20100160648
    Abstract: This invention provides an improved process for preparing cis-6-phenyl-5-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-2-methoxy-5,6,7,8-tetrahydronaphthalene hydrochloride which is an intermediate for the preparation of (?)-cis-6-phenyl-5-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-5,6,7,8-tetrahydronaphthalene-2-ol which is useful for the treatment of osteoporosis.
    Type: Application
    Filed: June 12, 2006
    Publication date: June 24, 2010
    Inventors: Geraldine Patricia Taber, Richard Shelton Lehner
  • Patent number: 7582653
    Abstract: Novel mercaptophenyl naphthyl methane compounds, their pharmaceutically acceptable salts and compositions comprised thereof are useful for the prevention or treatment of various medical indications associated with estrogen dependent diseases or syndromes related to osteoporosis, bone loss, bone formation, cardiovascular disorders, neurodegenerative disorders, menopausal disorders, physiological disorders, diabetes disorders, prostatic carcinoma, cancer of breast, cancer of uterus, cancer of the cervix and cancer of the colon, threatened or habitual abortion, obesity, ovarian development or function, post-partum lactation and depression.
    Type: Grant
    Filed: June 15, 2007
    Date of Patent: September 1, 2009
    Assignee: Council of Scientific & Industrial Research
    Inventors: Sangita, Atul Kumar, Man Mohan Singh, Girish Kumar Jain, Puvvada Sri Ramanchandra Murthy, Suprabhat Ray
  • Publication number: 20090062374
    Abstract: The present application describes deuterium-enriched lasofoxifene, pharmaceutically acceptable salt forms thereof, and methods of treating using the same.
    Type: Application
    Filed: August 25, 2008
    Publication date: March 5, 2009
    Applicant: PROTIA, LLC
    Inventor: Anthony W. Czarnik
  • Publication number: 20080227814
    Abstract: The present invention relates to a selective estrogen receptor modulator selected from the group consisting of: (I) or a pharmaceutical salt thereof; useful, e.g., for treating endometriosis and uterine leiomyoma.
    Type: Application
    Filed: January 18, 2005
    Publication date: September 18, 2008
    Inventors: Jeffrey Alan Dodge, Scott Alan Frank, Ronald Jay Hinklin, Owen Brendan Wallace
  • Patent number: 6812244
    Abstract: The instant invention provides novel substituted naphthyl compounds, intermediates, compositions, pharmaceutical formulations, and methods of use.
    Type: Grant
    Filed: May 27, 2003
    Date of Patent: November 2, 2004
    Assignee: Eli Lilly and Company
    Inventors: Henry Uhlman Bryant, Thomas Alan Crowell, Charles David Jones, Alan David Palkowitz
  • Patent number: 6610705
    Abstract: The invention relates to novel diaryl naphthyl methane compounds having general formula I as shown herein below, and said compounds useful in the treatment of esterogen related disease or syndrome, Pharmaceutical compositions comprising said novel methane derivatives, process for the preparation of the novel methane derivatives and methods for the treatment of esterogen related diseases or syndrome.
    Type: Grant
    Filed: March 31, 2000
    Date of Patent: August 26, 2003
    Assignee: Council of Scientific and Industrial Research
    Inventors: Neeta Srivastava, Arvinder Grover
  • Patent number: 6599920
    Abstract: This invention relates to the field of pharmaceutical and organic chemistry and provides naphthalene compounds, intermediates, formulations, and methods.
    Type: Grant
    Filed: August 26, 1997
    Date of Patent: July 29, 2003
    Assignee: Eli Lilly and Company
    Inventors: Henry Uhlman Bryant, Thomas Alan Crowell, Charles David Jones
  • Publication number: 20020183554
    Abstract: This invention encompasses novel methods of preparing sibutramine and sibutramine derivatives, and stereomerically pure sibutramine derivatives in particular. Examples of sibutramine derivatives include, but are not limited to, sibutramine metabolites such as desmethylsibutramine and didesmethylsibutramine. The invention further encompasses novel compounds useful in the synthesis of sibutramine derivatives.
    Type: Application
    Filed: April 12, 2002
    Publication date: December 5, 2002
    Inventors: Chris Hugh Senanayake, Zhengxu Han, Dhileepkumar Krishnamurthy, Derek Pflum
  • Patent number: 6455572
    Abstract: This invention relates to compounds that are mammalian metabolites of (−)-cis-6-phenyl-5-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-5,6,7,8-tetrahydro-naphthalene-2-ol. The compounds of the invention can be used as standards for analytical assays or as intermediates for the further chemical synthesis or biosynthesis of chemical entities. The invention also relates to pharmaceutical compositions for the treatment of disease and methods of treating disease.
    Type: Grant
    Filed: April 4, 2001
    Date of Patent: September 24, 2002
    Assignee: Pfizer Inc.
    Inventors: Wesley W. Day, Kim A. Johnson, Chandra A. Prakash, James F. Eggler
  • Patent number: 6444688
    Abstract: The instant invention provides compounds of formula I wherein R1 is OH, O—C(O)—(C1-C6 alkyl), O—C(O)—O(C1-C6 alkyl), O—C(O)—Ar, or O—C(O)—O—Ar; R2 is H, OH, O(C1-C6 alkyl), O—C(O)—(C1-C6 alkyl), O—C(O)—O(C1-C6 alkyl), O—C(O)—Ar, O—C(O)—O—Ar, O—SO2—(C4-C6 alkyl), chloro, fluoro, or bromo; V is S, O, or CH2CH2; W is CHOH, C(O), or CH2; X is (CH2)n; R3 and R4 each, independently, are H, C1-C6 alkyl, C(O)—(C1-C6 alkyl), C(O)—NH—(C1-C6 alkyl), C(O)—Ar, or together with the nitrogen to which they are attached form a 5- or 6-membered imide or cyclic amide; n is 1, 2, or 3; and Ar is optionally substituted phenyl; povided that at least one of R3 and R4 contains a carbonyl functional group, and their use in the treatment of estrogen deficiency pathologies.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: September 3, 2002
    Assignee: Eli Lilly and Company
    Inventors: Jeffrey A. Dodge, Charles D. Jones, Kristin Marron, James P. Sluka, Mark G. Stocksdale
  • Patent number: 6410564
    Abstract: The present invention provides a compound of formula I wherein R1 is —H, —OH, —O(C1-C4 alkyl) , —OCOC6H5, —OCO(C1-C6 alkyl), or —OSO2 (C4-C6 alkyl); R2 is —H, —OH, —O(C1-C4 alkyl), —OCOC6H5, —OCO(C1-C6 alkyl) or —OSO2 (C4-C6 alkyl); n is 2 or 3; and R3 is 1-piperidinyl, 1-pyrrolidinyl, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidinyl, 4-morpholino, dimethylamino, diethylamino, or 1-hexamethyleneimino; or a pharmaceutically acceptable salt thereof. Compounds of formula I are useful in treating osteoporosis, cardiovascular related pathological conditions, and estrogen-dependent cancer.
    Type: Grant
    Filed: April 21, 1995
    Date of Patent: June 25, 2002
    Assignee: Eli Lilly and Company
    Inventors: Henry U. Bryant, George J. Cullinan, Jeffrey A. Dodge, Kennan J. Fahey, Charles D. Jones, Charles W. Lugar, Brian S. Muehl
  • Patent number: 5998442
    Abstract: The invention provides benzo[b]thiophene compounds, formulations, and methods of inhibiting bone loss or bone resorption, particularly osteoporosis, and cardiovascular-related pathological conditions including hyperlipidemia and related cardiovascular pathologies.
    Type: Grant
    Filed: August 27, 1997
    Date of Patent: December 7, 1999
    Assignee: Eli Lilly and Company
    Inventors: Stephen Sung Yong Cho, Timothy Alan Grese, Lewis Dale Pennington
  • Patent number: 5998401
    Abstract: A class of substituted phenoxy naphthalene compounds of the structure: ##STR1## where n is 2 or 3; R.sup.1 is hydrogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, phenoxycarbonyl, C.sub.1 -C.sub.6 alkoxycarbonyl, or C.sub.2 -C.sub.6 alkoxy-sulfonyl; R.sup.2 is is hydrogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, phenoxycarbonyl, C.sub.1 -C.sub.6 alkoxycarbonyl, or C.sub.2 -C.sub.6 alkoxy-sulfonyl, or halo; and R.sup.3 is 1-piperidinyl, 1-pyrollidinyl, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidinyl, 4-morpholino, dimethylamino, diethylamino, diisopropylamino, or 1-hexamethyleneimino; are useful in the treatment of pathological conditions associated with post-menopause including osteoporosis, endometriosis, uterine fibroid disease, cardiovascular disease (particularly hyperlipidemia), and hormonally-dependent cancers (particularly breast and uterine cancer).
    Type: Grant
    Filed: February 28, 1995
    Date of Patent: December 7, 1999
    Assignee: Eli Lilly and Company
    Inventor: Alan D. Palkowitz
  • Patent number: 5959103
    Abstract: The invention provides naphthofluorene compounds, intermediates, formulations, processes, and methods of inhibiting bone loss or bone resorption, particularly osteoporosis, cardiovascular-related pathological conditions, including hyperlipidemia, and estrogen-dependent cancer.
    Type: Grant
    Filed: September 30, 1998
    Date of Patent: September 28, 1999
    Assignee: Eli Lilly and Company
    Inventors: Henry Uhlman Bryant, Jeffrey Alan Dodge, Charles Willis Lugar, III
  • Patent number: 5952350
    Abstract: The invention provides a compound of formula I: ##STR1## or a pharmaceutically acceptable salt or solvate thereof; pharmaceutical compositions containing a compound of formula I, and methods of using a compound of formula I for inhibiting bone loss or bone resorption, particularly osteoporosis, and cardiovascular-related pathological conditions including hyperlipidemia, and estrogen dependent cancer.
    Type: Grant
    Filed: October 23, 1997
    Date of Patent: September 14, 1999
    Assignee: Eli Lilly and Company
    Inventors: George Joseph Cullinan, Brian Stephen Muehl
  • Patent number: 5948809
    Abstract: (-)Cis-6(S)-phenyl-5(R)-?4-(2-pyrrolidin-1-yl ethoxy)phenyl!-5,6,7,8-tetrahydro-naphthalen-2-ol D-tartrate, pharmaceutical compositions comprising this compound, and an advantageous process for preparing the compound.
    Type: Grant
    Filed: April 28, 1998
    Date of Patent: September 7, 1999
    Assignee: Pfizer Inc
    Inventors: Charles K. Chiu, Morgan Meltz
  • Patent number: 5811421
    Abstract: The present invention provides compounds of formula ##STR1## wherein R.sup.1 is --H, --OH, --O(C.sub.1 -C.sub.4 alkyl), --OCOC.sub.6 H.sub.5, --OCO(C.sub.1 -C.sub.6 alkyl), or --OSO.sub.2 (C.sub.4 -C.sub.6 alkyl);R.sup.2 is C.sub.1 -C.sub.6 alkyl or C.sub.5 -C.sub.7 cycloalkyl which is optionally substituted with 1 to 3 substitutents selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, hydroxy, amino, nitro, and halo;X is --CH(OH)-- or --CH.sub.2 --;M is --CH.sub.2 CH.sub.2 -- or --CH.dbd.CH--;n is 2 or 3; andR.sup.3 is 1-piperidinyl, 1-pyrrolidinyl, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidinyl, 4-morpholino, dimethylamino, diethylamino, or 1-hexamethyleneimino; or a pharmaceutically acceptable salt thereof. Also provided are methods of using the compounds of the present invention for the treatment of various medical indications associated with post-menopausal syndrome, uterine fibroid disease, endometriosis, and aortal smooth muscle cell proliferation.
    Type: Grant
    Filed: July 16, 1996
    Date of Patent: September 22, 1998
    Assignee: Eli Lilly and Company
    Inventors: Jeffrey Alan Dodge, Kennan Joseph Fahey, Charles David Jones, Charles Willis Lugar, III
  • Patent number: 5700947
    Abstract: This invention is directed to nitric esters of derivatives of propionic acid, 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetic acid, 5-benzoyl-1,2-dihydro-3H-pyrrolo?1,2-a!pyrrole-1-carboxylic acid, 6-methoxy-2-napthylacetic acid, characterized in that they have the following general formula: ##STR1## These nitric ester derivatives may be formulated into pharmaceutical compositions and administered for their anti-inflammatory and/or analgesic activity.
    Type: Grant
    Filed: April 5, 1996
    Date of Patent: December 23, 1997
    Assignee: NICOX S.A.
    Inventor: Piero Del Soldato
  • Patent number: 5691353
    Abstract: The present invention provides a compound of formula I ##STR1## wherein R.sub.1 is H, OH, halo, OCO(C.sub.1 -C.sub.6 alkyl), OCO(aryl), OSO.sub.2 (C.sub.4 -C.sub.6 alkyl), OCOO(C.sub.1 -C.sub.6 alkyl), OCOO(aryl), OCONH (C.sub.1 -C.sub.6 alkyl), or OCON(C.sub.1 -C.sub.6 alkyl).sub.2 ;R.sub.2 is aryl, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, or 4-cyclohexanol;R.sub.3 is O(CH.sub.2).sub.2 or O(CH.sub.2).sub.3 ;R.sub.4 and R.sub.5 are optionally CO(CH.sub.2).sub.3,CO(CH.sub.2).sub.4, C.sub.1 -C.sub.6 alkyl, or R.sub.4 and R.sub.5 combine to form, with the nitrogen to which they are attached, piperidine, morpholine, pyrollidine, 3-methylpyrollidine, 3,3-dimethylpyrollidine, 3,4-dimethylpyrollidine, azepine, or pipecoline;R.sub.6 is>CH(C.sub.1 -C.sub.5 alkyl), >CH(C.sub.2 -C.sub.5 alkenyl), >C.dbd.CH(C.sub.1 -C.sub.5 alkyl), >CH(aryl), >C(OH)(C.sub.1 -C.sub.5 alkyl), >C(OH)(C.sub.2 -C.sub.5 alkenyl), C(OH)aryl;and phamaceutically acceptable salts thereof.
    Type: Grant
    Filed: December 5, 1995
    Date of Patent: November 25, 1997
    Assignee: Eli Lilly and Company
    Inventors: Henry U. Bryant, Jeffrey A. Dodge
  • Patent number: 5484795
    Abstract: The present invention provides a compound of formula I ##STR1## wherein R.sup.1 is --H, --OH, --O(C.sub.1 -C.sub.4 alkyl), --OCOC.sub.6 H.sub.5, --OCO(C.sub.1 -C.sub.6 alkyl), or --OSO.sub.2 (C.sub.4 -C.sub.6 alkyl);R.sup.2 is --H, --OH, --O(C.sub.1 -C.sub.4 alkyl), --OCOC.sub.6 H.sub.5, --OCO(C.sub.1 -C.sub.6 alkyl) or --OSO.sub.2 (C.sub.4 -C.sub.6 alkyl);n is 2 or 3; andR.sup.3 is 1-piperidinyl, 1-pyrrolidinyl, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidinyl, 4-morpholino, dimethylamino, diethylamino, or 1-hexamethyleneimino; or a pharmaceutically acceptable salt thereof, for treating restenosis.
    Type: Grant
    Filed: April 21, 1995
    Date of Patent: January 16, 1996
    Assignee: Eli Lilly and Company
    Inventors: Henry U. Bryant, George J. Cullinan, Jeffrey A. Dodge, Kennan J. Fahey, Charles D. Jones, Charles W. Lugar, Brian S. Muehl
  • Patent number: 5484796
    Abstract: The present invention provides a compound of formula I ##STR1## wherein R.sup.1 is --H, --OH, --O(C.sub.1 -C.sub.4 alkyl), --OCOC.sub.6 H.sub.5, --OCO(C.sub.1 -C.sub.6 alkyl), or --OSO.sub.2 (C.sub.4 -C.sub.6 alkyl);R.sup.2 is --H, --OH, --O(C.sub.1 -C.sub.4 alkyl), --OCOC.sub.6 H.sub.5, --OCO(C.sub.1 -C.sub.6 alkyl) or --OSO.sub.2 (C.sub.4 -C.sub.6 alkyl);n is 2 or 3; andR.sup.3 is 1-piperidinyl, 1-pyrrolidinyl, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidinyl, 4-morpholino, dimethylamino, diethylamino, or 1-hexamethyleneimino; or a pharmaceutically acceptable salt thereof, for inhibiting aortal smooth muscle cell proliferation.
    Type: Grant
    Filed: April 21, 1995
    Date of Patent: January 16, 1996
    Assignee: Eli Lilly and Company
    Inventors: Henry U. Bryant, George J. Cullinan, Jeffrey A. Dodge, Kennan J. Fahey, Charles D. Jones, Charles W. Lugar, Brian S. Muehl
  • Patent number: 5272144
    Abstract: Aryloxy- and heteroaryloxy-alkylene derivatives of amines of formula ##STR1## wherein each of A and B is a group of formula (i) to (iii): ##STR2## wherein Y is --O--, --S-- or --NR-- in which R is hydrogen or C.sub.1 -C.sub.6 alkyl; each of R.sub.3, R.sub.4, R.sub.5 and R.sub.6 is independently:a) hydrogen, halogen, hydroxy, cyano or nitro;b) C.sub.1 -C.sub.6 alkyl unsubstituted or substituted by halogen,c) C.sub.1 -C.sub.6 alkoxy or C.sub.1 -C.sub.6 alkylthio;d) C.sub.1 -C.sub.6 alkyl-sulfonyl;e) a substituted amine group --NR.sub.7 R.sub.8 ;f) a --COR.sub.12 group; org) two adjacent groups of R.sub.3, R.sub.4, R.sub.5 and R.sub.6, taken together, form a C.sub.1 -C.sub.4 alkylenedioxy group;each of R.sub.1 and R.sub.2 independently is hydrogen, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 alkenyl or C.sub.1 -C.sub.6 alkyl unsubstituted or substituted by phenyl; or R.sub.1 and R.sub.
    Type: Grant
    Filed: June 13, 1991
    Date of Patent: December 21, 1993
    Assignee: Farmitalia Carlo Erba s.r.l.
    Inventors: Piero Melloni, Philippe Dostert, Arturo D. Torre, Alberto Bonsignori
  • Patent number: 5250562
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 each independently are lower-alkyl; or together are alkylene with 3-5 C-atoms in a straight chain; one of the residues R.sup.3 and R.sup.4 is hydrogen and the other is hydrogen or lower-alkyl; R.sup.6 and R.sup.7 are hydrogen or lower-alkyl; R.sup.5 and R.sup.8 are hydrogen, lower-alkyl, lower-alkoxy or halogen; X signifies --O--, --S--, --SO--, --SO.sub.2 -- or --NR.sup.9 ; R.sup.9 is hydrogen, lower-alkyl or acyl; Y is --S(O).sub.m R.sup.10 or --NHet and, where X is --NR.sup.9 --, --S--, --SO-- or --SO.sub.2 --, also --N(R.sup.11).sub.2 or --OR.sup.12 ; R.sup.10 is lower-alkyl; R.sup.11 and R.sup.12 are hydrogen, lower-alkyl or acyl; --NHet is a 5-8 membered, saturated or unsaturated, monocyclic heterocycle attached via a N-atom; n is 2, 3 or 4 and m is 0, 1 or 2, are described. The compounds of formula I are useful as agents for the treatment of disorders such as neoplasms, dermatoses or ageing of the skin.
    Type: Grant
    Filed: February 3, 1992
    Date of Patent: October 5, 1993
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Peter Mohr, Ekkehard Weiss
  • Patent number: 5149714
    Abstract: The present invention provides novel aryloxy indanamines of the formula ##STR1## wherein n, p and q are each independently 0, 1 or 2,Y and X are each independently lower alkyl, lower alkoxy, hydroxy, CF.sub.3, halogeno or when p or q are 2 and each of the Y or each of the X groups are on adjacent aryl carbon atoms, both of the X or both of the Y groups can be taken together to form a methylenedioxy moiety,R.sub.1 and R.sub.2 are each independently hydrogen, lower alkyl, aralkyl, or R.sub.1 and R.sub.2 taken together with the nitrogen to which they are attached are pyrrolidino, morpholino, piperidino, piperazino, or 4-methylpiperazino,or an acid addition salt thereof, which are useful as antidepressants and as inhibitors of synaptic norepinephrine and serotonin uptake.
    Type: Grant
    Filed: August 15, 1990
    Date of Patent: September 22, 1992
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventor: Jules Freedman
  • Patent number: 5128362
    Abstract: The present invention provides compounds of the formula ##STR1## or a pharmaceutically acceptable salt thereof wherein R.sub.1 is selected from hydrogen, halo, lower alkyl, lower alkoxy, or thioalkoxy; and R.sub.2 is lower alkoxy; or R.sub.1 and R.sub.2 together form a methylenedioxy or ethylenedioxy ring; R.sub.3 and R.sub.4 are independently selected from hydrogen, hydroxy, lower alkyl, lower alkoxy, lower alkylthio, (lower alkyl)amino, (lower alkylsulfonyl)amino, and halo; and R.sub.7 is selected from the group consisting of 2- or 3-thienyl, 2- or 3-furyl, and ##STR2## where R.sub.13 and R.sub.14 are independently selected from the group consisting of hydrogen, hydroxy, halogen, amino, lower alkyl, lower alkoxy, lower alkylthio, methylenedioxy, or ethylenedioxy.The compounds of the present invention selectively inhibit .alpha..sub.2 -adrenergic receptors as well as inhibit the uptake of biogenic amines and are thus useful in the treatment of certain cardiovascular and psychiatric disorders.
    Type: Grant
    Filed: January 25, 1990
    Date of Patent: July 7, 1992
    Assignee: Abbott Laboratories
    Inventors: John F. DeBernardis, Robert E. Zelle, Fatima Z. Basha
  • Patent number: 4996215
    Abstract: A new piperidine compound is pharmacologically effective for treatment of the arrythmia and is defined by the formula: ##STR1## in which R.sup.1 is a lower alkyl or a tolyl, R.sup.2 is hydrogen, hydroxyl, a lower alkoxy or a lower alkyl, R.sup.3 is hydrogen, a lower alkyl, a lower alkenyl, a cycloalkyl or a cycloalkylalkyl, X is --CO--, --CH.sub.2 -- or --CHOH--, g is an integer of 1 to 3, h is an integer of 1 to 3, Y is hydrogen, a lower alkyl, a lower alkenyl, cyano, --CH.sub.2 COOR, R being hydrogen or a lower alkyl, a cycloalkyl, a cycloalkylalkyl, ##STR2## l being 1 or 2, --A--B, A being --(CH.sub.2).sub.
    Type: Grant
    Filed: September 15, 1989
    Date of Patent: February 26, 1991
    Assignee: Eisai Co., Ltd.
    Inventors: Hitoshi Oinuma, Motosuke Yamanaka, Kazutoshi Miyake, Tomonori Hoshiko, Norio Minami, Tadao Shoji, Yoshiharu Daiku, Kohei Sawada, Kenichi Nomoto
  • Patent number: 4933346
    Abstract: Compounds I are described ##STR1## with R.sup.1 equal to (cyclo)alk(en)yl or ##STR2## R.sup.2 /R.sup.3 equal to phenyl or phenylalkyl, A equal to ##STR3## m equal to 2-4, and n equal to 1-4.Compounds I and their salts are calcium antagonists.
    Type: Grant
    Filed: May 10, 1988
    Date of Patent: June 12, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Ruger, Hansjorg Urbach, Joachim Kaiser
  • Patent number: 4824968
    Abstract: Aromatic sulfonamides with a saturated heterocycle fused thereto are carbonic anhydrase inhibitors useful in the treatment of elevated intraocular pressure.
    Type: Grant
    Filed: June 26, 1987
    Date of Patent: April 25, 1989
    Assignee: Merck & Co., Inc.
    Inventors: Gerald S. Ponticello, J. Mark Wiggins
  • Patent number: 4732896
    Abstract: New aromatic derivatives having an activity antagonistic to calcium and corresponding to formula: ##STR1## in which: A represents a chain having any one of the following structures: ##STR2## Ar represents a group of structure: ##STR3## n takes the value 1 or 2 when R is different from H; m takes the value 2 or 3.
    Type: Grant
    Filed: June 26, 1985
    Date of Patent: March 22, 1988
    Assignee: Delalande S.A.
    Inventors: Guy R. Bourgery, Alain P. Lacour, Bernard M. Pourrias, Raphael Santamaria
  • Patent number: 4678855
    Abstract: Benzenesulfonamides with a substituted-alkyl-S(O).sub.n -substituent are carbonic anhydrase inhibitors useful in the treatment of elevated intraocular pressure.
    Type: Grant
    Filed: October 9, 1985
    Date of Patent: July 7, 1987
    Assignee: Merck & Co., Inc.
    Inventor: Kenneth L. Shepard
  • Patent number: 4504663
    Abstract: The present invention concerns novel heterocyclic aminoalcoyl derivatives having the formula: ##STR1## wherein n=1, 2 or 3; A represents a nitrogen atom or the CH group, X=CH.sub.2 or CH.sub.2 O; R represents a phenyl nucleus possibly substituted; NR.sub.1 R.sub.2 =amino, methylamino, N,N-dialkylamino or an heterocyclic radical; and R.sub.3 =H, halogen, alkyl, alkyloxy or methoxy.These derivatives are useful as drugs, especially as analgesics and antidepressants.
    Type: Grant
    Filed: November 15, 1983
    Date of Patent: March 12, 1985
    Assignee: Delalande S.A.
    Inventors: Gerard H. Moinet, Philippe L. Dostert, Guy R. Bourgery
  • Patent number: 4431851
    Abstract: The present invention concerns compounds of the formula ##STR1## wherein n=1, 2 or 3; and R' represents phenyl or orthofluorophenyl. Said compounds are used as intermediates in the preparation of heterocyclic aminoalkyl derivatives which are useful as analgesics and antidepressants.
    Type: Grant
    Filed: March 8, 1983
    Date of Patent: February 14, 1984
    Assignee: Delalande S.A.
    Inventors: Gerard H. Moinet, Philippe L. Dostert, Guy R. Bourgery
  • Patent number: 4342762
    Abstract: The invention relates to novel basic ethers of the general formula /I/ and pharmaceutically acceptable acid addition salts and quaternary salts thereof, ##STR1## wherein R.sup.1 and R.sup.2 may be the same or different and represent a C.sub.1-5 alkyl group or a C.sub.3-6 cycloalkyl group or they form, together with the adjacent nitrogen atom, a heterocyclic ring containing 4-7 carbon atoms and optionally a further hetero atom, e.g. an oxygen, sulfur or nitrogen atom, and this latter may be optionally substituted by a C.sub.1-3 alkyl, benzyl or phenyl group,R represents a phenyl, phenyl-/C.sub.1-3 alkyl/ or thienyl group optionally substituted by one or more halogen or C.sub.1-3 alkoxy substituent/s/,A represents a C.sub.2-5 straight or branched alkylene chain, and represents a valence bond of .alpha. or .beta. configuration.
    Type: Grant
    Filed: December 11, 1980
    Date of Patent: August 3, 1982
    Assignee: Egyt Gyogyszervegyeszeti Gyar
    Inventors: Zoltan Budai, Laszlo Magdanyi, Aranka Lay nee Konya, Tibor Mezei, Katalin Grasser, Lujza Petocz, Ibolya Kosoczky
  • Patent number: RE39419
    Abstract: This invention relates to compounds that are mammalian metabolites of (?)-cis-6-phenyl-5-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-5,6,7,8-tetrahydro-naphthalene-2-ol. The compounds of the invention can be used as standards for analytical assays or as intermediates for the further chemical synthesis or biosynthesis of chemical entities. The invention also relates to pharmaceutical compositions for the treatment of disease and methods of treating disease.
    Type: Grant
    Filed: May 30, 2003
    Date of Patent: December 5, 2006
    Assignee: Pfizer Inc.
    Inventors: Wesley W. Day, Kim A. Johnson, Chandra A. Prakash, James F. Eggler