3-Aryloxy-3-phenylpropylamines and acid addition salts thereof are useful in blocking uptake of monoamines by brain neurons, and are thus effective in treating disorders of sleep, sexual performance, appetite, muscular function, and pituitary function. |
Citations|
| US2683742 | Feb 23, 1951 | Jul 13, 1954 | | ATENT OFFICE | | US3106564 | Aug 21, 1958 | Oct 8, 1963 | | Z-PHENOXX-Z-PHENYLETHYL | | US3132179 | Aug 27, 1959 | May 5, 1964 | | CHOOC | | US3253040 | Dec 10, 1962 | May 24, 1966 | | PROCESS FOR THE PRODUCTION OF PRIMARY
J-HYDROCARBYLOXYPROPYLAMENES | | US3562330 | Jul 18, 1968 | Feb 9, 1971 | | PHENOXY-X. AND S-PHENYL-BUTYL AND
-PENTYL-AMINES AND SALTS | | US4018895 | Sep 17, 1975 | Apr 19, 1977 | Eli Lilly and Company | Aryloxyphenylpropylamines in treating depression | | US4194009 | Sep 15, 1976 | Mar 18, 1980 | Eli Lilly and Company | Aryloxyphenylpropylamines for obtaining a psychotropic effect | | US4313896 | Mar 9, 1981 | Feb 2, 1982 | Eli Lilly and Company | Aryloxyphenylpropylamines | | US4314081 | Jan 10, 1974 | Feb 2, 1982 | Eli Lilly and Company | Arloxyphenylpropylamines |
Referenced by|
| US4692469 | Apr 4, 1986 | Sep 8, 1987 | CIBA-GEIGY Corporation | Propylamine derivatives | | US4824868 | Jul 17, 1987 | Apr 25, 1989 | Ciba-Geigy Corporation Ciba-Geigy Corporation | Propylamine derivatives useful for the treatment of dementia | | US4895845 | Sep 15, 1986 | Jan 23, 1990 | | Method of assisting weight loss | | US4940585 | Feb 17, 1989 | Jul 10, 1990 | | Method for the treatment of nicotine withdrawal syndrome | | US4956388 | Jan 12, 1990 | Sep 11, 1990 | Eli Lilly and Company | 3-aryloxy-3-substituted propanamines | | US5104899 | Aug 13, 1990 | Apr 14, 1992 | Sepracor, Inc. | Methods and compositions for treating depression using optically pure fluoxetine | | US5114976 | Nov 5, 1990 | May 19, 1992 | | Method for treating certain psychiatric disorders and certain psychiatric symptoms | | US5229417 | Dec 5, 1991 | Jul 20, 1993 | Hoechst-Roussel Pharmaceuticals Incorporated | 2-(3-phenylpropyl)hydrazines and method of treating personality disorders | | US5238959 | Apr 20, 1992 | Aug 24, 1993 | Eli Lilly and Company | 3-phenyloxy-3-phenyl propanamines | | US5250571 | Apr 21, 1992 | Oct 5, 1993 | Eli Lilly and Company | (S)-norfluoxetine in method of inhibiting serotonin uptake | | US5250572 | Apr 21, 1992 | Oct 5, 1993 | Eli Lilly and Company | (R)-norfluoxetine in method for occupying serotonin IC receptors | | US5268468 | May 24, 1993 | Dec 7, 1993 | Hoechst-Roussel Pharmaceuticals Incorporated | N-nitrosophenoxybenzenepropanamine and N-1-chloroethyl carbamate intermediates | | US5281624 | Sep 27, 1991 | Jan 25, 1994 | Eli Lilly and Company | N-alkyl-3-phenyl-3-(2-substituted phenoxy) propylamines and pharmaceutical use thereof | | US5283263 | Apr 17, 1992 | Feb 1, 1994 | | Method for treating certain psychiatric disorders and certain psychiatric symptoms | | US5397122 | Feb 28, 1994 | Mar 14, 1995 | | Golf club swing connecting device | | US5525705 | Jan 31, 1995 | Jun 11, 1996 | Eli Lilly and Company | Anti-obesity proteins | | US5527788 | Jan 18, 1994 | Jun 18, 1996 | Louisiana State Univ. Medical Center Foundation | Method and composition for treating obesity comprising dehydroepiandrosterone (DHEA), or a derivative thereof, and an anorectic agent | | US5532336 | Jan 31, 1995 | Jul 2, 1996 | Eli Lilly and Company | Anti-obesity proteins | | US5552522 | Jan 31, 1995 | Sep 3, 1996 | Eli Lilly and Company | Anti-obesity proteins | | US5552523 | Feb 6, 1995 | Sep 3, 1996 | Eli Lilly and Company | Anti-obesity proteins | | US5552524 | Feb 6, 1995 | Sep 3, 1996 | Eli Lilly and Company | Anti-obesity proteins | | US5554727 | Feb 6, 1995 | Sep 10, 1996 | Eli Lilly and Company | Anti-obesity proteins | | US5563243 | Jan 31, 1995 | Oct 8, 1996 | Eli Lilly and Company | Anti-obesity proteins | | US5563244 | Jan 31, 1995 | Oct 8, 1996 | Eli Lilly and Company | Anti-obesity proteins | | US5563245 | Jan 31, 1995 | Oct 8, 1996 | Eli Lilly and Company | Anti-obesity proteins | | US5567678 | Jan 31, 1995 | Oct 22, 1996 | Eli Lilly and Company | Anti-obesity proteins | | US5567803 | Feb 6, 1995 | Oct 22, 1996 | Eli Lilly and Company | Anti-obesity proteins | | US5569744 | Feb 6, 1995 | Oct 29, 1996 | Eli Lilly and Company | Anti-obesity proteins | | US5574133 | Jan 31, 1995 | Nov 12, 1996 | Eli Lilly and Company | Anti-obesity proteins | | US5580954 | Jan 31, 1995 | Dec 3, 1996 | Eli Lilly and Company | Anti-obesity proteins | | US5589511 | Apr 15, 1994 | Dec 31, 1996 | Sepracor Inc. | Method for treating migraine headaches using optically pure S(+) fluoxetine | | US5589512 | Jan 25, 1994 | Dec 31, 1996 | | Method for treating borderline personality disorder with serotonin re-uptake blockers | | US5594101 | Mar 3, 1995 | Jan 14, 1997 | Eli Lilly and Company | Anti-obesity proteins | | US5594104 | Feb 6, 1995 | Jan 14, 1997 | Eli Lilly and Company | Anti-obesity proteins | | US5605886 | May 17, 1995 | Feb 25, 1997 | Eli Lilly and Company | Anti-obesity proteins | | US5648396 | Jun 7, 1995 | Jul 15, 1997 | Sepracor Inc. | Methods for treating depression and other disorders using optically pure R (-) fluoxetine and monoamine oxidase inhibitor | | US5691309 | Feb 6, 1995 | Nov 25, 1997 | Eli Lilly and Company | Anti-obesity proteins | | US5708035 | May 22, 1995 | Jan 13, 1998 | Sepracor Inc. McLean Hospital | Methods of use and compositions of R(-) fluoxetine | | US5719266 | Mar 17, 1995 | Feb 17, 1998 | Eli Lilly and Company | Anti-obesity proteins | | US5744501 | Mar 11, 1997 | Apr 28, 1998 | | Method for treating late luteal phase dysphoric disorder | | US5789449 | Sep 19, 1996 | Aug 4, 1998 | | Treatment of symptoms associated with premenstrual disorders | | US5795880 | Dec 30, 1996 | Aug 18, 1998 | Louisiana State University Medical Center Foundation | Method and composition for treating obesity and related disorders in animals comprising dehydroepiandrosterone (DHEA), or a derivative thereof, and an anorectic agent | | US5830500 | Jul 22, 1996 | Nov 3, 1998 | Pentech Pharmaceuticals, Inc. | Low dose fluoxetine tablet | | US5851995 | Aug 4, 1997 | Dec 22, 1998 | Eli Lilly and Company | Anti-obesity proteins | | US5910319 | May 29, 1997 | Jun 8, 1999 | Eli Lilly and Company | Fluoxetine enteric pellets and methods for their preparation and use | | US5936124 | Jun 22, 1998 | Aug 10, 1999 | Sepacor Inc. | Fluoxetine process from benzoylpropionic acid | | US5985322 | Mar 10, 1999 | Nov 16, 1999 | Eli Lilly and Company | Method for the treatment of CNS disorders | | US6017965 | Dec 11, 1996 | Jan 25, 2000 | NPS Pharmaceuticals, Inc. | Compounds active at a novel site on receptor-operated calcium channels useful for treatment of neurological disorders and diseases | | US6025517 | Aug 3, 1998 | Feb 15, 2000 | Sepracor Inc. | Fluoxetine process from benzoylacetonitrile | | US6028224 | May 24, 1999 | Feb 22, 2000 | Sepracor Inc. | Fluoxetine process from benzoylpropionic acid | | US6203817 | Jun 5, 1998 | Mar 20, 2001 | ALZA Corporation | Reduction of skin reactions caused by transdermal drug delivery | | US6258853 | Jan 31, 2001 | Jul 10, 2001 | | Form a of fluoxetine hydrochloride | | US6273260 | Mar 8, 2000 | Aug 14, 2001 | Eli Lilly and Company | Pharmaceutical packaging system | | US6310250 | Jan 31, 2001 | Oct 30, 2001 | | Form A of fluoxetine hydrochloride | | US6310251 | Jan 31, 2001 | Oct 30, 2001 | | Form a of fluoxetine hydrochloride | | US6313350 | Jan 31, 2001 | Nov 6, 2001 | | Form a of fluoxetine hydrochloride | | US6316672 | Jan 31, 2001 | Nov 13, 2001 | | Form a of fluoxetine hydrochloride | | US6395509 | May 26, 1995 | May 28, 2002 | Eli Lilly and Company | DNA encoding Rhesus ob protein | | US6492556 | Nov 5, 2001 | Dec 10, 2002 | | Form A of fluoxetine hydrochloride | | US6512010 | Jul 14, 1997 | Jan 28, 2003 | Alza Corporation | Formulations for the administration of fluoxetine | | US6982251 | Jun 11, 2002 | Jan 3, 2006 | Schering Corporation | Substituted 2-azetidinones useful as hypocholesterolemic agents | | US7011844 | Nov 22, 2002 | Mar 14, 2006 | Alza Corporation | Formulations for the administration of fluoxetine | | US7030106 | May 1, 2002 | Apr 18, 2006 | Schering Corporation | Sterol absorption inhibitor compositions | | US7034059 | Jun 28, 2002 | Apr 25, 2006 | Sepracor Inc. | Methods of using norfluoxetine | | US7053080 | Sep 19, 2002 | May 30, 2006 | Schering Corporation | Methods and therapeutic combinations for the treatment of obesity using sterol absorption inhibitors | | US7071181 | Sep 19, 2002 | Jul 4, 2006 | Schering Corporation | Methods and therapeutic combinations for the treatment of diabetes using sterol absorption inhibitors | | US7132415 | Sep 19, 2002 | Nov 7, 2006 | Schering Corporation | Methods and therapeutic combinations for the treatment of xanthoma using sterol absorption inhibitors | | US7189755 | Feb 10, 2004 | Mar 13, 2007 | Palatin Technologies, Inc. | Pyrrolidine melanocortin-specific compounds | | US7192944 | Mar 3, 2004 | Mar 20, 2007 | Schering Corp. | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof | | US7208486 | Mar 3, 2004 | Apr 24, 2007 | Schering Corporation | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof | | US7235543 | Mar 3, 2004 | Jun 26, 2007 | Schering Corporation | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof | | US7268166 | Feb 13, 2006 | Sep 11, 2007 | NPS Pharmaceuticals, Inc. | Compounds active at a novel site on receptor-operated calcium channels useful for treatment of neurological disorders and diseases | | US7326707 | Jan 21, 2004 | Feb 5, 2008 | Palatin Technologies Incorporated | Bicyclic melanocortin-specific compounds | | US7326733 | Jun 2, 2003 | Feb 5, 2008 | The Forsyth Institute | Methods for increasing bone density | | US7354923 | Jan 21, 2004 | Apr 8, 2008 | Palatin Technologies, Inc. | Piperazine melanocortin-specific compounds | | US7368562 | Feb 13, 2007 | May 6, 2008 | Schering Corporation | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof | | US7368563 | Feb 13, 2007 | May 6, 2008 | Schering Corporation | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof | | US7378518 | Feb 20, 2007 | May 27, 2008 | Schering Corporation | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof | | US7417039 | Jan 25, 2002 | Aug 26, 2008 | Schering Corporation | Use of substituted azetidinone compounds for the treatment of sitosterolemia | | US7456184 | Apr 30, 2004 | Nov 25, 2008 | Palatin Technologies Inc. | Melanocortin receptor-specific compounds | | US7459442 | Apr 24, 2008 | Dec 2, 2008 | Schering Corporation | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof | | US7560449 | Nov 4, 2003 | Jul 14, 2009 | Schering Corporation | Methods and therapeutic combinations for the treatment of demyelination | | US7601753 | Mar 1, 2007 | Oct 13, 2009 | Palatin Technologies, Inc. | Pyrrolidine melanocortin-specific compounds | | US7612058 | Nov 29, 2004 | Nov 3, 2009 | Schering Corporation | Methods for inhibiting sterol absorption | | US7655658 | Jan 21, 2005 | Feb 2, 2010 | Palatin Technologies, Inc. | Thieno [2,3-D]pyrimidine-2,4-dione melanocortin-specific compounds | | US7709484 | Apr 19, 2005 | May 4, 2010 | Palatin Technologies, Inc. | Substituted melanocortin receptor-specific piperazine compounds | | US7718802 | Apr 5, 2005 | May 18, 2010 | Palatin Technologies, Inc. | Substituted melanocortin receptor-specific piperazine compounds | | US7727990 | Aug 11, 2006 | Jun 1, 2010 | Palatin Technologies, Inc. | Melanocortin receptor-specific piperazine and keto-piperazine compounds | | US7727991 | Aug 11, 2006 | Jun 1, 2010 | Palatin Technologies, Inc. | Substituted melanocortin receptor-specific single acyl piperazine compounds | | US7732413 | Apr 24, 2008 | Jun 8, 2010 | Schering Corporation | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof | | US7732451 | Jan 14, 2005 | Jun 8, 2010 | Palatin Technologies, Inc. | Naphthalene-containing melanocortin receptor-specific small molecule | | US7741289 | Apr 22, 2008 | Jun 22, 2010 | Schering Corporation | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof | | US7807678 | Feb 10, 2004 | Oct 5, 2010 | Palatin Technologies, Inc. | Peptidomimetics of biologically active metallopeptides | | US7834017 | Aug 10, 2007 | Nov 16, 2010 | Palatin Technologies, Inc. | Diamine-containing, tetra-substituted piperazine compounds having identical 1- and 4-substituents | | US7964601 | Jun 2, 2008 | Jun 21, 2011 | Palatin Technologies, Inc. | Melanocortin receptor-specific compounds | | US7968548 | Aug 11, 2006 | Jun 28, 2011 | Palatin Technologies, Inc. | Melanocortin receptor-specific piperazine compounds with diamine groups | | USRE39030 | Jan 28, 2002 | Mar 21, 2006 | Eli Lilly and Company | Fluoxetine enteric pellets and methods for their preparation and use |
Claims1. A method of treating animals suffering from an appetite disorder comprising administering to said animal an effective amount of a compound of the formula ##STR7## wherein each R' is independently hydrogen or methyl; wherein R is naphthyl or ##STR8## wherein R" and R"' are halo, trifluoromethyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkyloxy or C.sub.3 -C.sub.4 alkenyl; and - wherein n and m are 0, 1 or 2; and acid addition salts thereof formed with pharmaceutically-acceptable acids.
2. A method according to claim 1 employing N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine or a pharmaceutically-acceptable acid addition salt thereof. 3. The method of claim 2 employing N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine hydrochloride. 4. A method of blocking the uptake of monoamines by brain neurons in animals comprising administering to said animal a monoamine blocking amount of a compound of the formula ##STR9## wherein each R' is independently hydrogen or methyl; wherein R is naphthyl or ##STR10## wherein R" and R"' are halo, trifluoromethyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkyloxy or C.sub.3 -C.sub.4 alkenyl; and - wherein n and m are 0, 1 or 2; and acid addition salts thereof formed with pharmaceutically-acceptable acids.
5. A method according to claim 4 wherein the monoamine to be blocked is serotonin. 6. A method according to claim 5 employing N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine or a pharmaceutically-acceptable acid addition salt thereof. 7. The method of claim 6 employing N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine hydrochloride. 8. The method of claim 5 employing N-methyl-3-(o-methylphenoxy)-3-phenylpropylamine or a pharmaceutically-acceptable acid addition salt thereof. 9. The method of claim 5 employing N-methyl-3-(o-methylphenoxy)-3-phenylpropylamine hydrochloride. |