Nitrogen Or Divalent Chalcogen Double Bonded Directly To Carbocyclic Ring Of The Pentacyclo Ring System (e.g., Morphinones, Etc.) Patents (Class 546/45)
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Publication number: 20080161570Abstract: Methods for the synthesis of 4,5-epoxy-morphinaniums using dimethyl formamide and resolution of the diastereomeric products by means of HPLC.Type: ApplicationFiled: November 19, 2007Publication date: July 3, 2008Applicant: Progenerics Pharmaceuticals, Inc.Inventors: Julio Perez, Amy Qi Han, Alfred A. Avey
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Publication number: 20080146804Abstract: Disclosed are methods for making aldehydes and ketones comprising allowing the corresponding primary or secondary alcohol to react in the presence of trichoroisocyanuric acid, a compound of formula R1SR2 and a base. In one embodiment, the alcohol is a compound of formula (I): wherein R3 is a protecting group. Also disclosed are methods for making 3-O-protected morphine dienol carboxylates comprising allowing a compound of formula (I) to oxidize in the presence of a chlorine-containing compound and a compound of formula R1SR2; and allowing the product of the oxidation step to react with an acylating agent.Type: ApplicationFiled: February 4, 2005Publication date: June 19, 2008Applicant: EURO-CELTIQUE S.A.Inventor: Andreas Stumpf
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Publication number: 20080146601Abstract: Improved analgesic oxymorphone hydrochloride contains less than 10 ppm of alpha, beta unsaturated ketones and pharmaceutical preparations comprising such oxymorphone hydrochloride. The oxymorphone hydrochloride is produced by reducing a starting material oxymorphone hydrochloride using gaseous hydrogen and under specified acidity, solvent system and temperature conditions. A specific polymorph of oxymorphone hydrochloride may be obtained by hydration.Type: ApplicationFiled: October 3, 2007Publication date: June 19, 2008Applicant: Johnson Matthey Public Limited CompanyInventors: Jen-Sen Dung, Emo M. Keskeny, James J. Mencel
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Publication number: 20080139814Abstract: The present invention is directed to processes for preparing oxycodone base and oxycodone hydrochloride compositions having less than 10 ppm of 14-hydroxycodeinone.Type: ApplicationFiled: December 4, 2007Publication date: June 12, 2008Inventors: D. Phillip Cox, Yong Zhang, Wen-Chun Zhang, Karen E. James
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Publication number: 20080132703Abstract: The present invention is directed to a process for using n-butanol to prepare an oxycodone base compositions having reduced levels of impurities such as 14-hydroxycodeinone and DHDHC.Type: ApplicationFiled: December 4, 2007Publication date: June 5, 2008Inventors: D. Phillip Cox, Yong Zhang
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Publication number: 20080125592Abstract: Methods are provided which include converting oripavine to other opiates, including converting oripavine to naltrexone, buprenorphine, 14-hydroxymorphinone and/or converting 14-hydroxymorphinone to oxymorphone. Purification and salt formation are optionally included.Type: ApplicationFiled: October 16, 2007Publication date: May 29, 2008Applicant: PENICK CORPORATIONInventor: Bao-Shan Huang
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Patent number: 7348430Abstract: The present invention includes a process for the manufacture of dihydrothebaine, dihydrocodeinone enol acetate, hydrocodone, and analogs thereof by reacting dihydrocodeine or analogs thereof with benzophenone in the presence of potassium tert-alkylate in a hydrocarbon solvent to generate a reaction mixture containing an enolate of the corresponding ketone, followed by addition of the reaction mixture to the electrophilic agent and isolation of the product.Type: GrantFiled: January 21, 2005Date of Patent: March 25, 2008Assignee: Acura Pharmaceuticals, Inc.Inventors: Igor R. Likhotvorik, Joseph J. Lisowski
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Publication number: 20080045558Abstract: The present disclosure is directed to modulators of opiate- and/or NMDA receptors and pharmaceutically acceptable salts and prodrugs thereof, the chemical synthesis thereof, and the use of such compounds for the treatment and/or management of pain, anxiety, neurodegeneration, drug dependence, coughing, muscular tension, and/or glaucoma and any other condition in which it is beneficial to modulate an opiate- and/or NMDA receptor.Type: ApplicationFiled: August 16, 2007Publication date: February 21, 2008Applicant: AUSPEX PHARMACEUTICALS, INC.Inventors: Thomas G. GANT, Sepehr SARSHAR
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Patent number: 7323565Abstract: A method for the catalytic conversion of codeine, morphine or analogs thereof into hydrocodone, hydromorphone or analogs thereof utilizing a transition metal complex of a tertiary phosphine halide as catalyst.Type: GrantFiled: November 5, 2003Date of Patent: January 29, 2008Assignee: Mallinckrodt Inc.Inventors: Peter Xianqi Wang, Carl Ray White
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Patent number: 7321038Abstract: A method for the catalytic conversion of codeine, morphine or analogs thereof into hydrocodone, hydromorphone or analogs thereof utilizing a transition metal catalyst of the formula [M(PR3R4R5)nXm]p; wherein R1 is H, alkyl, aryl or acyl; M is a Group VIII transition metal; R3, R4 and R5 are selected from the group consisting of alkyl, aryl, alkoxyl, phenoxyl and combinations thereof; X is a halide or an anion; n is 1, 2, 3 or 4; m is 1 or 2; and p is at least 1.Type: GrantFiled: October 25, 2004Date of Patent: January 22, 2008Assignee: Mallinckrodt Inc.Inventors: Peter Xianqi Wang, Carl Ray White
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Patent number: 7285665Abstract: A process for the preparation of a quaternary derivative of the morphinan alkaloid, the process comprising contacting a tertiary N-substituted morphinan alkaloid with an alkyl halide in an anhydrous solvent system, wherein the solvent system comprises an aprotic dipolar solvent with the aprotic dipolar solvent constituting at least 25 wt. % of the solvent system.Type: GrantFiled: November 5, 2003Date of Patent: October 23, 2007Assignee: Mallinckrodt Inc.Inventors: Gary L. Cantrell, Robert E. Halvachs
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Patent number: 7199129Abstract: The present disclosure concerns compounds of formula (I) and pharmaceutically acceptable salts, hydrates, solvates, pharmaceutically acceptable derivatives, pro-drugs, tautomers and/or isomers thereof.Type: GrantFiled: August 9, 2002Date of Patent: April 3, 2007Assignees: Monash University, Neuro Therapeutics LimitedInventors: William Roy Jackson, Kamani Rupika Subasinghe
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Patent number: 7164021Abstract: Novel compounds which selectively bind to the ?-opioid receptor have been designed. These compounds have greater selectivity, improved water (blood) solubility, and enhanced therapeutic value as analgesics. Because agonists with selectivity for the ?-opioid receptor have shown promise in providing enhanced analgesis without the addictive properties, the compounds of the present invention are better than morphine, naltrindole (NTI), spiroindanyloxymorphone (SIOM), and other known ?-opioid receptor selectors as analgesics.Type: GrantFiled: September 18, 2003Date of Patent: January 16, 2007Assignee: The Curators of The University of MissouriInventors: William J. Welsh, Seong Jae Yu, Anil Nair
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Patent number: 7153966Abstract: A process for preparing oxycodone or an oxycodone salt, wherein the oxycodone or oxycodone salt has low levels of impurities (especially 14-hydroxycodeinone) is disclosed. The process comprises the steps of: a) preparing a mixture comprising oxycodone and a solvent and adjusting the pH of the mixture to less than 6; and subsequently b) exposing the mixture to hydrogenation reagents for a period of at least 1 hour.Type: GrantFiled: September 23, 2005Date of Patent: December 26, 2006Assignee: Johnson Matthey Public Limited CompanyInventors: Michael Lawrence Casner, Jen-Sen Dung, Erno M. Keskeny, Jin Luo
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Patent number: 7129248Abstract: In certain embodiments the invention is directed to a process for preparing an oxycodone hydrochloride composition having less than 25 ppm of 14-hydroxycodeinone.Type: GrantFiled: March 30, 2005Date of Patent: October 31, 2006Assignee: Euro-Celtique, S.A.Inventors: Robert Chapman, Lonn S. Rider, Qi Hong, Donald Kyle, Robert Kupper
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Patent number: 7071336Abstract: Oxycodone is manufactured in high yields and with a high purity using a composition including a thebaine component into 14-hydroxycodeinone and then reduction of 14-hydroxycodeinone to oxycodone.Type: GrantFiled: July 16, 2004Date of Patent: July 4, 2006Assignee: Acura PharmaceuticalsInventors: Charles Auxilium Francis, Zhaiwei Lin, Christopher Arne Kaldahl, Kazimierz Grzegorz Antczak, Vijai Kumar
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Patent number: 7060708Abstract: The present invention relates to active agent delivery systems and more specifically to compositions that comprise amino acids, as single amino acids or peptides, covalently attached to active agents and methods for administering conjugated active agent compositions.Type: GrantFiled: May 29, 2002Date of Patent: June 13, 2006Assignee: New River Pharmaceuticals Inc.Inventors: Thomas Piccariello, Randal J. Kirk, Travis Mickle
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Patent number: 6946556Abstract: A one-pot process for preparing opioid analgesics such as hydrocodone, hydromorphone, and analogues thereof by reacting codeine, morphine, and analogues thereof with hydrogen in a solvent system of benzophenone and neutral solvent in the presence of a metal catalyst followed by oxidation in the presence of potassium tert-alkylate.Type: GrantFiled: May 21, 2004Date of Patent: September 20, 2005Assignee: Acura Pharmaceuticals, Inc.Inventors: Igor Likhotvorik, Joseph J. Lisowski
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Patent number: 6864370Abstract: Oxycodone is manufactured in high yields and with a high purity using codeine or a salt of codeine as the starting material. The manufacturing process involves the following steps: (a) codeine or a codeine salt (e.g.Type: GrantFiled: June 5, 2003Date of Patent: March 8, 2005Inventors: Zhaiwei Lin, Charles Auxilium Francis, Christopher Arne Kaldahl, Kazimierz Grzegorz Antczak, Vijai Kumar
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Publication number: 20040242616Abstract: The present disclosure concerns compounds of formula (I) and pharmaceutically acceptable salts, hydrates, solvates, pharmaceutically acceptable derivatives, pro-drugs, tautomers and/or isomers thereof. The disclosure also relates to processes for the preparation of compounds according to formula (I), pharmaceutical or veterinary compositions containing such compounds or methods of treatment and/or prophylaxis of a condition or symptom that is inhibited, reduced or alleviated by opioid receptor activation.Type: ApplicationFiled: June 21, 2004Publication date: December 2, 2004Inventors: William Roy Jackson, Kamani Rupika Subasinghe
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Patent number: 6825205Abstract: This invention relates to N-substituted hydromorphones of Formula I: or a pharmaceutically acceptable salt thereof, wherein R is C1-6 alkyl. These compounds act as &mgr; opioid receptor agonists. The invention is also directed to the use of compounds of Formula I for the treatment, prevention or amelioration of both acute and chronic pain.Type: GrantFiled: September 24, 2003Date of Patent: November 30, 2004Assignee: Euro-Celtique S.A.Inventor: Donald J. Kyle
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Patent number: 6784186Abstract: This invention relates to novel structural analogues and derivatives of compounds with general analgesic or related pharmacological activity. In particular the invention relates to derivatives of opioid compounds, particularly morphine and related compounds, in which an opioid compound is linked via the nitrogen at position 17 to a spacer group, which in turn is linked to a charged group, or a pharmaceutically acceptable salt thereof. In particularly preferred embodiments the opioid compound is morphine, codeine, or buprenorphine.Type: GrantFiled: November 20, 2000Date of Patent: August 31, 2004Inventors: Roy W. Jackson, Kamani R. Subasinghe, Alan L. A. Boura
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Patent number: 6740641Abstract: Glucoside and glucuronide derivatives of hydromorphone, dihydromorphine, and dihydroisomorphine and pharmaceutically acceptable salts thereof; pharmaceutical compositions comprising a glucoside or glucuronide derivative of hydromorphone, dihydromorphine, or dihydroisomorphine or a pharmaceutically acceptable salt thereof; and methods for treating or preventing pain in a patient comprising administering to a patient in need thereof a glucoside or glucuronide derivative of hydromorphone, dihydromorphine, or dihydroisomorphine or a pharmaceutically acceptable salt thereof are disclosed.Type: GrantFiled: July 22, 2002Date of Patent: May 25, 2004Assignee: Euro-Celtique, S.A.Inventors: Feng Gao, Jahanara Miotto
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Publication number: 20040067973Abstract: This invention relates to N-substituted hydromorphones of Formula I: 1Type: ApplicationFiled: September 24, 2003Publication date: April 8, 2004Applicant: Euro-Celtique S.A.Inventor: Donald J. Kyle
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Publication number: 20040058946Abstract: One aspect of the present invention relates to compositions and methods for discouraging improper use of habit-forming and addictive drugs, such as oxycodone. In a preferred embodiment, a habit-forming or addictive drug is chemically modified to block its physiological activity until the drug is transformed to a physiologically active form in the mammalian gastrointestinal tract.Type: ApplicationFiled: July 3, 2003Publication date: March 25, 2004Inventors: Stephen L. Buchwald, Timothy M. Swager, Roman V. Rariy
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Patent number: 6696457Abstract: Heterocycle condensed morphinoid derivatives of formula (I) have therapeutic utility as analgesics, in collagen disease, as anti-allergic and anti-inflammatory agents, brain cell protectants, in gastritis, diarrhoea, cardiovascular and respiratory diseases, cough, mental illness, epilepsy, for the preservation of organs during transplant operations, and for the treatment of those pathological conditions which customarily can be treated with agonists of the delta opioid receptor.Type: GrantFiled: April 2, 2002Date of Patent: February 24, 2004Assignees: SmithKline Beecham p.l.c., SmithKline Beecham S.p.A.Inventors: Stephen Edward Clarke, Giulio Dondio, Luca Francesco Raveglia, Silvano Ronzoni
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Publication number: 20030157565Abstract: Novel haptens, which can be conjugated to form immunogens, are of formula I, II or III 1Type: ApplicationFiled: December 20, 2002Publication date: August 21, 2003Applicant: RANDOX LABORATORIES LTD.Inventors: John Victor Lamont, Robert Ivan McConnell, Stephen Peter Fitzgerald, El Ouard Benchikh, Andrew Philip Lowry
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Publication number: 20030153096Abstract: A water-soluble reference standard is useful for immunoassays of a lipophilic drugs.Type: ApplicationFiled: January 25, 2002Publication date: August 14, 2003Inventors: Min Li, Robert S. Wu, Jane S.C. Tsai
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Patent number: 6589960Abstract: A method for the preparation of a ketone from a narcotic alkaloid having an allyl alcohol moiety is disclosed. The method includes mixing the narcotic alkaloid with an acid in the presence of a catalyst wherein the method is carried out in the substantial absence of hydrogen gas. The method is useful for preparing hydromorphone and hydrocodone compositions having novel impurity profiles. Compositions comprising hydromorphone and hydrocodone are also disclosed.Type: GrantFiled: September 27, 2002Date of Patent: July 8, 2003Assignee: Abbott LaboratoriesInventors: William H. Harclerode, Robert Gault, Mark D. Sandison
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Patent number: 6559159Abstract: Structurally novel kappa opioid receptor antagonists are provided and the use of these antagonists in treatment of disease states that are ameliorated by binding of the kappa opioid receptor such as heroin or cocaine addictions.Type: GrantFiled: February 1, 2001Date of Patent: May 6, 2003Assignee: Research Triangle InstituteInventors: F. Ivy Carroll, James B. Thomas, S. Wayne Mascarella
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Patent number: 6512117Abstract: A method for the preparation of a ketone from a narcotic alkaloid having an allyl alcohol moiety is disclosed. The method includes mixing the narcotic alkaloid with an acid in the presence of a catalyst wherein the method is carried out in the substantial absence of hydrogen gas. The method is useful for preparing hydromorphone and hydrocodone compositions having novel impurity profiles. Compositions comprising hydromorphone and hydrocodone are also disclosed.Type: GrantFiled: November 9, 2000Date of Patent: January 28, 2003Assignee: Abbott LaboratoriesInventors: William H. Harclerode, Robert Gault, Mark D. Sandison
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Patent number: 6469170Abstract: A method for the preparation of oxycodone, and salts thereof, from codeine comprising oxidation of codeine to codeinone, formation of an dienolsilyl ether congener of codeinone in strong amine base, oxidation of the dienolsilyl ether congener using peracetic acid, and hydrogenation of the resulting 14-hydroxycodeinone product.Type: GrantFiled: May 21, 2002Date of Patent: October 22, 2002Assignee: Boehringer Ingelheim Chemicals, Inc.Inventors: Fang-Ting Chiu, Young S. Lo
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Patent number: 6440987Abstract: This invention provides an antipuritic comprising an opiate &kgr; receptor agonist as an effective component, a new morphian quaternary ammonium salt derivative and a new morphian-N-oxide derivative which are useful in treating puritus complicated with some diseases.Type: GrantFiled: October 4, 2001Date of Patent: August 27, 2002Assignee: Toray Industries, Inc.Inventors: Hiroshi Nagase, Takashi Endoh, Toshiaki Tanaka, Kuniaki Kawamura
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Patent number: 6403798Abstract: A method for the preparation of oxycodone, and salts thereof, from codeine comprising oxidation of codeine to codeinone, formation of an dienolsilyl ether congener of codeinone in strong amine base, oxidation of the dienolsilyl ether congener using peracetic acid, and hydrogenation of the resulting 14-hydroxycodeinone product.Type: GrantFiled: February 26, 2001Date of Patent: June 11, 2002Assignee: Boehringer Ingelheim Chemicals, Inc.Inventors: Fang-Ting Chiu, Young S. Lo
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Patent number: 6376221Abstract: There is disclosed an improved poppy straw of a stably reproducing Papaver somniferum for the extraction of thebaine and/or oripavine, the threshed straw having thebaine and oripavine constituting about 50% by weight or greater of the alkaloid combination consisting of morphine, codeine, thebaine and oripavine.Type: GrantFiled: August 31, 1999Date of Patent: April 23, 2002Assignee: Tasmanian Alkaloids Pty. Ltd.Inventors: Anthony John Fist, Christopher James Byrne, Wayne Lyle Gerlach
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Patent number: 6365594Abstract: Heterocycle-condensed morphinoid derivatives of formula (I), or solvates or salts thereof, are potent and selective delta opioid agonists and antagonists and are useful as i.a. analgesics. Pharmaceutical compositions containing such compounds, the use of such compounds as therapeutic agents, a method of treatment comprising the administration of such compounds, and a process for the preparation of such compounds are also described.Type: GrantFiled: February 22, 1999Date of Patent: April 2, 2002Assignee: SmithKline Beecham S.p.A.Inventors: Giulio Dondio, Silvano Ronzoni, Pier Andrea Gatti, Davide Graziani
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Patent number: 6365742Abstract: A process for the preparation of thebaine, its salts such as the bitartrate, and analogues thereof, together with a novel intermediate useful in said process are disclosed. Thebaine bitartrate is itself useful in the preparation of oxycodone; analogues are useful in the preparation of analogous 14-hydroxymorphinones.Type: GrantFiled: May 15, 2000Date of Patent: April 2, 2002Assignee: Johnson Matthey Public Limited CompanyInventors: Bogdan Mudryk, Chester Sapino, Jen-Sen Dung, Alice Sebastian
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Patent number: 6359111Abstract: A compound comprising a ligand portion which has binding affinity for an opioid receptor, and a therapeutically or diagnostically effective group selected from radionuclide chelating agents, fluorochromes, toxins, drugs, polyboron moieties, proteins, biological response modifiers, chemical moieties capable of binding to other molecules of interest, and radioisotopes selected from therapeutically effective alpha and beta emitters, and diagnostically effective gamma emitters. The compound may be used in a method of treating cancer, and in a method of imaging opioid receptors either inside or outside of the central nervous system.Type: GrantFiled: May 27, 1999Date of Patent: March 19, 2002Assignee: NeoRx CorporationInventors: Damon L. Meyer, Sudhakar Kasina
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Patent number: 6316461Abstract: This invention provides an antipruritc comprising an opiate &kgr; receptor agonist as an effective component, a new morphinan quaternary ammonium salt derivative and a new morphinan-N-oxide derivative which are useful in treating pruritus complicated with some diseases.Type: GrantFiled: July 13, 2000Date of Patent: November 13, 2001Assignee: Toray Industries, Inc.Inventors: Hiroshi Nagase, Jun Utsumi, Takashi Endoh, Toshiaki Tanaka, Junzo Kamei, Kuniaki Kawamura
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Publication number: 20010018519Abstract: A novel process for the preparation of codeinone and analogues thereof comprising the oxidation of a compound of formula, 1Type: ApplicationFiled: April 17, 2001Publication date: August 30, 2001Applicant: Johnson Matthey Public Limited CompanyInventor: Alice Sebastian
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Patent number: 6277859Abstract: A morphinan derivative or its pharmacologically allowed acid addition salt represented with compound I, an analgesic and diuretic having its derivative or its salt as the active ingredient, and its production process are described. The compound of the present invention possesses strong analgesic activity and diuretic action as a highly selective &kgr;-opioid agonist, allowing it to be used as a useful analgesic and diuretic.Type: GrantFiled: March 31, 2000Date of Patent: August 21, 2001Assignee: Toray Industries, Inc.Inventors: Hiroshi Nagase, Koji Kawai, Kuniaki Kawamura, Jun Hayakawa, Takashi Endoh
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Publication number: 20010005754Abstract: A method for the preparation of oxycodone, and salts thereof, from codeine comprising oxidation of codeine to codeinone, formation of an dienolsilyl ether congener of codeinone in strong amine base, oxidation of the dienolsilyl ether congener using peracetic acid, and hydrogenation of the resulting 14-hydroxycodeinone product.Type: ApplicationFiled: February 26, 2001Publication date: June 28, 2001Inventors: Fang-Ting Chiu, Young S. Lo
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Patent number: 6235906Abstract: A novel process for the preparation of codeinone and analogues thereof comprising the oxidation of a compound of formula, or a salt thereof, wherein R1 is lower alkyl or a group wherein R4 is lower alkyl, lower alkyl substituted by halogen or phenyl, phenyl or substituted phenyl; and R2 is lower alkyl, allyl or lower alkyl substituted by cycloalkyl, characterized in that the oxidation is carried out in an acidic environment is disclosed.Type: GrantFiled: March 17, 1999Date of Patent: May 22, 2001Assignee: Johnson Matthey Public Limited CompanyInventor: Alice Sebastian
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Patent number: 6225321Abstract: The nalbuphine polyester derivative is related to a novel long acting agent. The nalbuphine polyester derivative is R—[CO-NAL]n wherein n is an integer from 2-4 and, in which the R is selected from a saturated or nonsaturated, substituted or unsubstituted, aliphatic or aromatic group having 1 to 40 carbon atoms. The process for producing the derivative includes esterifying nalbuphine with a saturated or unsaturated fatty acid or a halogen compound of the fatty acid with an acid anhydride. A pharmaceutical composition contains the derivative and a pharmaceutically acceptable carrier, which can be administered to an animal or person for treating pain.Type: GrantFiled: June 5, 1997Date of Patent: May 1, 2001Inventors: Oliver Yoa-Pu Hu, Shung-Tai Ho, Fangchen Lee
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Patent number: 6194422Abstract: The present invention provides imino aza-anthracyclinones and a method of treating amyloidoses using the same.Type: GrantFiled: July 27, 1999Date of Patent: February 27, 2001Assignee: Pharmacia & Upjohn SpAInventors: Michele Caruso, Daniela Faiardi, Tiziano Bandiera, Jacqueline Lansen, Antonino Suarato
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Patent number: 6187783Abstract: A novel phenanthridinium derivative represented by general formula (A): wherein R1 is a substituted or unsubstituted lower aliphatic hydrocarbon group; R is an aliphatic hydrocarbon chain having 2 to 6 carbon atoms which may optionally be substituted with a substituent selected from the group consisting of a lower alkyl group, a halogen and a hydroxy group; each of Y and Z independently represents a hydrogen, a hydroxy or a lower alkoxy group; or Y and Z are combined together to form methylenedioxy or a phenyl ring; and, X− is an acid residue or a hydrogen acid residue, exhibits an antitumor activity and has resistance to chemical reduction as well as biological metabolic reactions and is thus advantageous for use as a medicine.Type: GrantFiled: May 20, 1999Date of Patent: February 13, 2001Assignee: Nippon Kayaku Kabushiki KaishaInventors: Akira Masuda, Masato Suwa, Masanobu Suzuki
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Patent number: 6177438Abstract: A morphinan derivative or its pharmaceutically acceptable acid addition salt represented with, for example, and an analgesic, diuretic, antitussive and brain cell protector having its derivative or its salt as the active ingredient are described. The compound of the present invention possesses strong analgesic activity, diuretic action and antitussive action as a highly selective &kgr;-opioid agonist, allowing it to be used as a useful analgesic, diuretic and antitussive. On the other hand, the compound of the present invention also possesses remarkable cerebro-neuroprotective activity, thus allowing it be used as a useful cerebro-neuroprotective agents.Type: GrantFiled: November 21, 1996Date of Patent: January 23, 2001Assignee: Toray Industries, Inc.Inventors: Hiroshi Nagase, Jun Hayakawa, Kuniaki Kawamura, Koji Kawai, Takashi Endoh
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Patent number: 6166211Abstract: The present invention pertains to a process for the preparation of the 10-keto analogs of morphinan compounds. In the case of compounds having a 3-hydroxyl group, the 3-methyl ether protected analog is synthesized by selective phenolic methylation in the presence of the basic amino group. When nalbuphine, morphine, or codeine is used as the starting material, the additional 6-hydroxyl group is protected using acetylation. The protected analog is selectively oxidized by treatment with cerium ammonium nitrate to provide the 10-(S)-hydroxy adduct. The 10-(S)-hydroxy adduct is further oxidized to the 10-keto analog. Any protecting groups that were added prior to oxidation are cleaved subsequent to oxidation to form the desired 10-ketomorphinan.Type: GrantFiled: March 7, 2000Date of Patent: December 26, 2000Assignee: Endo Pharmaceuticals, Inc.Inventors: Gary A. Cain, Spencer Drummond, Jr.
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Patent number: 6136817Abstract: New morphinane derivatives of the formula ##STR1## their pharmaceutically acceptable salts, a process for their preparation and their use in the manufacture of pharmaceutical preparations.Type: GrantFiled: August 22, 1995Date of Patent: October 24, 2000Assignee: Astra ABInventor: Helmut Schmidhammer
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Patent number: 6124310Abstract: The present invention provides compounds of formulae (I) and (II), where X in formula (I) represents a group cleavable by a nitroreductase or carboxypeptidase enzyme. Enzymatic activation of the compounds provide pharmaceutical compounds which may be used for the treatment of neoplastic disease.Type: GrantFiled: April 17, 1998Date of Patent: September 26, 2000Assignee: Mewburn EllisInventors: William Alexander Denny, Michael Patrick Hay, William Robert Wilson