CS214738B2 - Method for the production of racemic and optically active derivatives of 2-pyrrolidone - Google Patents

Method for the production of racemic and optically active derivatives of 2-pyrrolidone Download PDF

Info

Publication number
CS214738B2
CS214738B2 CS751860A CS186075A CS214738B2 CS 214738 B2 CS214738 B2 CS 214738B2 CS 751860 A CS751860 A CS 751860A CS 186075 A CS186075 A CS 186075A CS 214738 B2 CS214738 B2 CS 214738B2
Authority
CS
Czechoslovakia
Prior art keywords
formula
pyrrolidone
group
alkyl
solvent
Prior art date
Application number
CS751860A
Other languages
Czech (cs)
English (en)
Inventor
Ralph Schmiechen
Reinhard Horowsky
Dieter Palenschat
Gert Paschelke
Helmut Wachtel
Wolfgang Kehr
Original Assignee
Schering Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Schering Ag filed Critical Schering Ag
Priority to CS802586A priority Critical patent/CS214739B2/cs
Publication of CS214738B2 publication Critical patent/CS214738B2/cs

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24Oxygen or sulfur atoms
    • C07D207/262-Pyrrolidones
    • C07D207/2732-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
    • C07D207/277Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/18Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00Carboxylic acid nitriles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00Compounds having —CHO groups
    • C07C47/52Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24Oxygen or sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24Oxygen or sulfur atoms
    • C07D207/262-Pyrrolidones
CS751860A 1974-03-20 1975-03-19 Method for the production of racemic and optically active derivatives of 2-pyrrolidone CS214738B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CS802586A CS214739B2 (cs) 1974-03-20 1980-04-14 Způsob výroby racemických a opticky aktivních derivátů 2-pyrrolidonu

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2413935A DE2413935A1 (de) 1974-03-20 1974-03-20 4-(polyalkoxy-phenyl)-2-pyrrolidone

Publications (1)

Publication Number Publication Date
CS214738B2 true CS214738B2 (en) 1982-05-28

Family

ID=5910915

Family Applications (1)

Application Number Title Priority Date Filing Date
CS751860A CS214738B2 (en) 1974-03-20 1975-03-19 Method for the production of racemic and optically active derivatives of 2-pyrrolidone

Country Status (20)

Country Link
US (1) US4012495A (de)
JP (1) JPS6011028B2 (de)
AT (1) AT347931B (de)
BE (1) BE826923A (de)
CA (1) CA1069517A (de)
CH (1) CH621338A5 (de)
CS (1) CS214738B2 (de)
DD (1) DD119229A5 (de)
DE (1) DE2413935A1 (de)
DK (1) DK139965C (de)
ES (1) ES435750A1 (de)
FR (1) FR2264531B1 (de)
GB (1) GB1498705A (de)
HU (1) HU174074B (de)
IE (1) IE40865B1 (de)
IL (1) IL46883A (de)
NL (1) NL7503367A (de)
SE (1) SE402010B (de)
SU (1) SU649312A3 (de)
YU (1) YU40258B (de)

Families Citing this family (114)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4193926A (en) 1974-03-20 1980-03-18 Schering Aktiengesellschaft 4-(Polyalkoxy phenyl)-2-pyrrolidones
DE2541855A1 (de) * 1975-09-18 1977-03-31 Schering Ag 4-(polyalkoxy-phenyl)-2-pyrrolidone ii
CU21107A3 (es) * 1978-02-10 1988-02-01 Hoffmann La Roche Pyrrolidines derivatives
IL57266A (en) 1978-06-12 1982-12-31 Mundipharma Ag Production of pyrrolidin-2-ones and of 3-pyrrolin-2-ones
IT1131959B (it) * 1979-08-09 1986-06-25 Hoffmann La Roche Derivati pirrolidinici
GB2123288A (en) * 1982-07-16 1984-02-01 Wellcome Found Anti-thrombotic agent
US4584313A (en) * 1984-05-07 1986-04-22 Warner-Lambert Company (Substituted-phenyl)-5-oxo-2-pyrrolidinepropanoic acids and esters thereof, and use for reversing electroconvulsive shock-induced amnesia
US4548947A (en) * 1984-05-07 1985-10-22 Warner-Lambert Company 1-(Substituted-aryl)-dihydro-1H-pyrrolizine-3,5-[2H,6H-]diones and use for reversing amnesia
US5783591A (en) * 1984-10-19 1998-07-21 Schering Aktiengesellschaft Administration of oxazolidinone and pyrolidinone compounds for the treatment of inflammation
DE3438839A1 (de) * 1984-10-19 1986-04-24 Schering AG, 1000 Berlin und 4709 Bergkamen Pharmazeutische praeparate
HU215433B (hu) * 1986-04-29 2000-05-28 Pfizer Inc. Eljárás új 2-oxo-5-fenil-pirimidin-származékok előállítására
US5459145A (en) * 1988-01-19 1995-10-17 Pfizer Inc. Calcium independent camp phosphodiesterase inhibitor antidepressant
FI875101A (fi) * 1986-12-03 1988-06-04 Tanabe Seiyaku Co Laktamderivat och preparat innehaollande dessa.
US4971959A (en) * 1987-04-14 1990-11-20 Warner-Lambert Company Trisubstituted phenyl analogs having activity for congestive heart failure
US5274002A (en) * 1987-04-14 1993-12-28 Warner-Lambert Company Trisubstituted phenyl analogs having activity for congestive heart failure
US4960457A (en) * 1988-12-27 1990-10-02 Ici Americas Inc. Substituted 1,3-diphenyl pyrrolidones and their use as herbicides
DD295358A5 (de) * 1989-06-28 1991-10-31 �����@������������������k�� Verfahren zur racemattrennung von 4-aryl-2-oxo-pyrrolidin-3-carbonsaeure-estern
JP2578001B2 (ja) * 1989-12-11 1997-02-05 明治製菓株式会社 抗痴呆薬
DE3943385A1 (de) * 1989-12-27 1991-07-04 Schering Ag Mittel zur transdermalen applikation enthaltend rolipram
DD299058A5 (de) * 1990-01-31 1992-03-26 Arzneimittelwerk Dresden Gmbh,De Verfahren zur herstellung von n-acyl-4-phenyl-pyrrolidin-2-onen mit cerebroprotektiver wirkung
GB9009395D0 (en) * 1990-04-26 1990-06-20 Orion Yhtymae Oy Cyclic hydroxamic acids and their use
AU8292091A (en) * 1990-08-03 1992-03-02 Smithkline Beecham Corporation Tnf inhibitors
DE4032055A1 (de) * 1990-10-05 1992-04-09 Schering Ag Verfahren zur herstellung von optisch aktiven 4-aryl-2-pyrrolidinonen
US5547979A (en) * 1992-03-30 1996-08-20 Smithkline Beecham TNF inhibition
US5395935A (en) * 1992-05-08 1995-03-07 Pfizer Inc. Endo-bicyclo[2.2.1]heptan-2-ol and derived pharmaceutical agents
GB9212673D0 (en) * 1992-06-15 1992-07-29 Celltech Ltd Chemical compounds
GB9222253D0 (en) * 1992-10-23 1992-12-09 Celltech Ltd Chemical compounds
US5622977A (en) * 1992-12-23 1997-04-22 Celltech Therapeutics Limited Tri-substituted (aryl or heteroaryl) derivatives and pharmaceutical compositions containing the same
GB9226830D0 (en) * 1992-12-23 1993-02-17 Celltech Ltd Chemical compounds
GB9304919D0 (en) * 1993-03-10 1993-04-28 Celltech Ltd Chemical compounds
GB9304920D0 (en) * 1993-03-10 1993-04-28 Celltech Ltd Chemical compounds
GB9312853D0 (en) 1993-06-22 1993-08-04 Euro Celtique Sa Chemical compounds
US5477611A (en) * 1993-09-20 1995-12-26 Tessera, Inc. Method of forming interface between die and chip carrier
US5665754A (en) * 1993-09-20 1997-09-09 Glaxo Wellcome Inc. Substituted pyrrolidines
EP0738268B1 (de) * 1993-12-22 2004-03-03 Celltech R&D Limited Trisubstituierte phenyl-derivate, verfahren zu deren herstellung und deren verwendung als phosphodiesterase (typ iv) hemmstoffe
GB9326173D0 (en) * 1993-12-22 1994-02-23 Celltech Ltd Chemical compounds and process
CA2143143A1 (en) * 1994-03-08 1995-09-09 Toshihiko Tanaka 3-phenylpyrrolidine derivatives
US5338739A (en) * 1994-03-10 1994-08-16 Hoechst-Roussel Pharmaceuticals Inc. (Pyrrolidinyl)phenyl carbamates, compositions and use
US5786354A (en) * 1994-06-21 1998-07-28 Celltech Therapeutics, Limited Tri-substituted phenyl derivatives and processes for their preparation
US6245774B1 (en) 1994-06-21 2001-06-12 Celltech Therapeutics Limited Tri-substituted phenyl or pyridine derivatives
GB9412571D0 (en) 1994-06-22 1994-08-10 Celltech Ltd Chemical compounds
GB9412573D0 (en) * 1994-06-22 1994-08-10 Celltech Ltd Chemical compounds
GB9412672D0 (en) * 1994-06-23 1994-08-10 Celltech Ltd Chemical compounds
US5922751A (en) 1994-06-24 1999-07-13 Euro-Celtique, S.A. Aryl pyrazole compound for inhibiting phosphodiesterase IV and methods of using same
US5591776A (en) * 1994-06-24 1997-01-07 Euro-Celtique, S.A. Pheynl or benzyl-substituted rolipram-based compounds for and method of inhibiting phosphodiesterase IV
US5665737B1 (en) * 1994-10-12 1999-02-16 Euro Celtique Sa Substituted benzoxazoles
US6025361A (en) 1994-12-13 2000-02-15 Euro-Celtique, S.A. Trisubstituted thioxanthines
EP0814809B1 (de) 1994-12-13 2003-08-13 Euroceltique S.A. Arylthioxanthine
AU706159B2 (en) * 1995-02-10 1999-06-10 Schering Aktiengesellschaft Pharmaceutical preparations for TNF inhibition
US6268373B1 (en) 1995-06-07 2001-07-31 Euro-Celtique S.A. Trisubstituted thioxanthines
US6166041A (en) 1995-10-11 2000-12-26 Euro-Celtique, S.A. 2-heteroaryl and 2-heterocyclic benzoxazoles as PDE IV inhibitors for the treatment of asthma
DE19540475A1 (de) * 1995-10-20 1997-04-24 Schering Ag Chirale Methylphenyloxazolidinone
GB9523675D0 (en) 1995-11-20 1996-01-24 Celltech Therapeutics Ltd Chemical compounds
GB9526245D0 (en) * 1995-12-21 1996-02-21 Celltech Therapeutics Ltd Chemical compounds
GB9526243D0 (en) * 1995-12-21 1996-02-21 Celltech Therapeutics Ltd Chemical compounds
GB9526246D0 (en) * 1995-12-21 1996-02-21 Celltech Therapeutics Ltd Chemical compounds
US6075016A (en) 1996-04-10 2000-06-13 Euro-Celtique S.A. 6,5-fused aromatic ring systems having enhanced phosphodiesterase IV inhibitory activity
GB9608435D0 (en) * 1996-04-24 1996-06-26 Celltech Therapeutics Ltd Chemical compounds
US5864037A (en) 1996-06-06 1999-01-26 Euro-Celtique, S.A. Methods for the synthesis of chemical compounds having PDE-IV inhibitory activity
JP4017214B2 (ja) 1996-06-11 2007-12-05 興和創薬株式会社 5−フェニル−3−ピリダジノン誘導体
DE69730980T2 (de) 1996-07-31 2006-02-23 Nikken Chemicals Co., Ltd. 6-phenyltetrahydro-1,3-oxazin-2-on derivate und medizinische zusammensetzungen, die sie enthalten
CA2264685C (en) 1996-08-27 2002-10-15 Kyoji Noda 2-phenylmorpholin-5-one derivatives and pharmaceutical composition comprising the same
US5744473A (en) * 1996-09-16 1998-04-28 Euro-Celtique, S.A. PDE IV inhibitors: "bis-compounds"
GB9619284D0 (en) * 1996-09-16 1996-10-30 Celltech Therapeutics Ltd Chemical compounds
GB9622363D0 (en) * 1996-10-28 1997-01-08 Celltech Therapeutics Ltd Chemical compounds
GB9625184D0 (en) * 1996-12-04 1997-01-22 Celltech Therapeutics Ltd Chemical compounds
US6057329A (en) * 1996-12-23 2000-05-02 Celltech Therapeutics Limited Fused polycyclic 2-aminopyrimidine derivatives
GB9705361D0 (en) 1997-03-14 1997-04-30 Celltech Therapeutics Ltd Chemical compounds
GB9713087D0 (en) * 1997-06-20 1997-08-27 Celltech Therapeutics Ltd Chemical compounds
US6235736B1 (en) 1997-06-24 2001-05-22 Nikken Chemicals Co., Ltd. 3-anilino-2-cycloalkenone derivatives
DE69824632T2 (de) 1997-11-12 2005-06-09 Mitsubishi Chemical Corp. Purinderivate und medikamente, welche dieselben als aktiven bestandteil enthalten
US7378400B2 (en) 1999-02-01 2008-05-27 University Of Virginia Patent Foundation Method to reduce an inflammatory response from arthritis
US7427606B2 (en) 1999-02-01 2008-09-23 University Of Virginia Patent Foundation Method to reduce inflammatory response in transplanted tissue
US6232297B1 (en) * 1999-02-01 2001-05-15 University Of Virginia Patent Foundation Methods and compositions for treating inflammatory response
WO2000068231A1 (fr) * 1999-05-11 2000-11-16 Mitsubishi Chemical Corporation Dihydrate derive de purine, medicaments le contenant comme principe actif et intermediaire utilise dans sa preparation
GB9914258D0 (en) * 1999-06-18 1999-08-18 Celltech Therapeutics Ltd Chemical compounds
JP5038568B2 (ja) 1999-08-21 2012-10-03 ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング 協力剤の組合せ物
GB9924862D0 (en) * 1999-10-20 1999-12-22 Celltech Therapeutics Ltd Chemical compounds
DE60125026T2 (de) * 2000-03-23 2007-06-28 Takeda Pharmaceutical Co. Ltd. Fluorisochinolinderivate, verfahren zu ihrer herstellung und ihre anwendung
PL367130A1 (en) * 2001-05-29 2005-02-21 Schering Aktiengesellschaft Cdk inhibiting pyrimidines, production thereof and their use as medicaments
DE60237244D1 (de) * 2001-07-16 2010-09-16 Merck Patent Gmbh Photostabile organische Sonnenschutzmittel mit antioxidativen Eigenschaften
JP4514452B2 (ja) * 2001-10-01 2010-07-28 ユニバーシティ オブ バージニア パテント ファウンデーション A2aアゴニスト活性を有する2−プロピルアデノシン・アナログおよびその組成物
RU2340600C2 (ru) * 2001-10-16 2008-12-10 Мемори Фармасьютиклз Корпорейшн Производные 4-(4-алкокси-3-гидроксифенил)-2-пирролидона в качестве ингибиторов pde-4 для лечения неврологических синдромов
WO2003086408A1 (en) * 2002-04-10 2003-10-23 University Of Virginia Patent Foundation Use of a2a adenosine receptor agonists for the treatment of inflammatory diseases
AU2003281691A1 (en) * 2002-07-26 2004-02-16 Takeda Pharmaceutical Company Limited Furoisoquinoline derivative and use thereof
US7495016B2 (en) * 2002-10-21 2009-02-24 Irm Llc Pyrrolidones with anti-HIV activity
US7772188B2 (en) 2003-01-28 2010-08-10 Ironwood Pharmaceuticals, Inc. Methods and compositions for the treatment of gastrointestinal disorders
BRPI0409229A (pt) 2003-04-01 2006-03-28 Applied Research Systems inibidores das fosfodiesterases na infertilidade
EP1613590A2 (de) 2003-04-16 2006-01-11 Memory Pharmaceutical Corporation 4-(3,4-disubstituiertes phenyl)-pyrrolidin-2-on-verbindungen als phosphodiesterase 4 inhibitoren
JP2006523719A (ja) * 2003-04-18 2006-10-19 メモリー・ファーマシューティカルズ・コーポレイション ホスホジエステラーゼ4抑制剤としてのピラゾール誘導体
AU2004234355A1 (en) * 2003-04-25 2004-11-11 Icos Corporation Method of preparing a ring compound having two adjacent chiral centers
CN1953968B (zh) * 2004-05-17 2012-10-10 大塚制药株式会社 噻唑化合物及其用途
US7576069B2 (en) 2004-08-02 2009-08-18 University Of Virginia Patent Foundation 2-polycyclic propynyl adenosine analogs having A2A agonist activity
CN101068825B (zh) 2004-08-02 2013-05-08 弗吉尼亚大学专利基金会 具有a2a激动剂活性的具有修饰的5'-核糖基团的2-丙炔基腺苷类似物
US7442687B2 (en) 2004-08-02 2008-10-28 The University Of Virginia Patent Foundation 2-polycyclic propynyl adenosine analogs having A2A agonist activity
WO2006044528A1 (en) 2004-10-15 2006-04-27 Memory Pharmaceuticals Corporation Pyrazole derivatives as phosphodiesterase 4 inhibitors
EP1802615A1 (de) * 2004-10-20 2007-07-04 Memory Pharmaceuticals Corporation Phosphodiesterase-4-inhibitoren
WO2007120972A2 (en) * 2006-02-10 2007-10-25 University Of Virginia Patent Foundation Method to treat sickle cell disease
US8188063B2 (en) * 2006-06-19 2012-05-29 University Of Virginia Patent Foundation Use of adenosine A2A modulators to treat spinal cord injury
US7879802B2 (en) 2007-06-04 2011-02-01 Synergy Pharmaceuticals Inc. Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders
US8969514B2 (en) 2007-06-04 2015-03-03 Synergy Pharmaceuticals, Inc. Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases
US8058259B2 (en) 2007-12-20 2011-11-15 University Of Virginia Patent Foundation Substituted 4-{3-[6-amino-9-(3,4-dihydroxy-tetrahydro-furan-2-yl)-9H-purin-2-yl]-prop-2-ynyl}-piperidine-1-carboxylic acid esters as A2AR agonists
EP3239170B1 (de) 2008-06-04 2019-03-20 Synergy Pharmaceuticals Inc. Für die behandlung von gastrointestinalen erkrankungen, entzündungen, krebs und anderen erkrankungen geeignete agonisten von guanylatcyclase
EP3241839B1 (de) 2008-07-16 2019-09-04 Bausch Health Ireland Limited Zur behandlung von erkrankungen des magen-darm-trakts, entzündlichen erkrankungen, krebs und anderen erkrankungen geeignete agonisten von guanylatcyclase
WO2010075086A2 (en) * 2008-12-15 2010-07-01 Auspex Pharmaceuticals, Inc. Pyrrolidinone inhibitors of pde-4
US9616097B2 (en) 2010-09-15 2017-04-11 Synergy Pharmaceuticals, Inc. Formulations of guanylate cyclase C agonists and methods of use
CN108676076A (zh) 2011-03-01 2018-10-19 辛纳吉制药公司 制备鸟苷酸环化酶c激动剂的方法
ES2395801B1 (es) 2011-06-23 2014-06-06 María Carmen PARDINA PALLEJÀ "pentoxifilina por vía transvaginal para el tratamiento de la infertilidad"
US9545446B2 (en) 2013-02-25 2017-01-17 Synergy Pharmaceuticals, Inc. Agonists of guanylate cyclase and their uses
US9708367B2 (en) 2013-03-15 2017-07-18 Synergy Pharmaceuticals, Inc. Agonists of guanylate cyclase and their uses
CA2905435A1 (en) 2013-03-15 2014-09-25 Synergy Pharmaceuticals Inc. Compositions useful for the treatment of gastrointestinal disorders
JP6606491B2 (ja) 2013-06-05 2019-11-13 シナジー ファーマシューティカルズ インコーポレイテッド グアニル酸シクラーゼcの超高純度アゴニスト、その作成および使用方法
IL280864B2 (en) 2013-08-09 2024-03-01 Ardelyx Inc Compounds and methods for inhibiting phosphate transport
WO2020237096A1 (en) 2019-05-21 2020-11-26 Ardelyx, Inc. Combination for lowering serum phosphate in a patient

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1516776A (fr) 1966-07-21 1968-03-15 Rhone Poulenc Sa Nouveaux dérivés du pyrrole et leur préparation
GB1350582A (en) * 1970-07-24 1974-04-18 Ucb Sa Cerivatives of 2-pyrrolidinone

Also Published As

Publication number Publication date
CA1069517A (en) 1980-01-08
ATA210975A (de) 1978-06-15
DD119229A5 (de) 1976-04-12
SU649312A3 (ru) 1979-02-25
ES435750A1 (es) 1976-12-16
AU7931075A (en) 1976-09-23
DK139965C (da) 1979-10-29
DE2413935A1 (de) 1975-10-16
YU63275A (en) 1982-06-30
YU40258B (en) 1985-10-31
JPS50157360A (de) 1975-12-19
AT347931B (de) 1979-01-25
DK139965B (da) 1979-05-28
DK110675A (de) 1975-09-21
BE826923A (fr) 1975-09-22
SE402010B (sv) 1978-06-12
HU174074B (hu) 1979-10-28
CH621338A5 (de) 1981-01-30
US4012495A (en) 1977-03-15
DE2413935C2 (de) 1988-05-26
IE40865B1 (en) 1979-08-29
GB1498705A (en) 1978-01-25
IE40865L (en) 1975-09-20
NL7503367A (nl) 1975-09-23
IL46883A0 (en) 1975-05-22
FR2264531A1 (de) 1975-10-17
IL46883A (en) 1979-09-30
FR2264531B1 (de) 1978-07-28
SE7503157L (sv) 1975-11-28
JPS6011028B2 (ja) 1985-03-22

Similar Documents

Publication Publication Date Title
CS214738B2 (en) Method for the production of racemic and optically active derivatives of 2-pyrrolidone
US4153713A (en) 4-(Polyalkoxyphenyl)-2-pyrrolidones (II)
US4193926A (en) 4-(Polyalkoxy phenyl)-2-pyrrolidones
US4837235A (en) Indole and indazole keto sulphones as leukotriene antagonists
US3799932A (en) Gamma-piperidinobutyrophenones
US4248884A (en) 2-Pyrrolidine methanol derivatives utilizable as medicaments
US3665010A (en) Substituted phenylacetic acids and esters thereof
US4567180A (en) Carboximide derivative and medicines containing same
US4148796A (en) γ-Piperidinobutyrophenones
AU646349B2 (en) Novel N-alkylated 1, 4-dihydropyridinedicarboxylic acid esters
US2995566A (en) Preparation of tryptamine derivatives
EP0106276B1 (de) 1,4-Dihydropyridin-Derivate
US4946862A (en) Thiophene derivative and process for preparing the same
US4663319A (en) 3-(1,3-dithiol-2-ylidene)-2,4-dioxopyrrolidines, -piperidines, and -hexahydroazepines and use thereof against hepatic diseases
US5364860A (en) Naphthyridine compounds which inhibit tyrosine kinase and their pharmaceutical compositions
US4806560A (en) Imidazo[4,5-b]pyridin-2-one derivatives
NO158019B (no) Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazolinderivater.
FR2707984A1 (fr) Nouvelles pipérazines substituées, leur procédé de préparation et les compositions les contenant.
US4906640A (en) 3-sulfonyl-3,7-diazabicyclo[3,3,1]nonane compounds and medicaments containing said compounds
CS214739B2 (cs) Způsob výroby racemických a opticky aktivních derivátů 2-pyrrolidonu
EP0090275A2 (de) Isoxazole (5,4-b) Pyridine
US4162252A (en) Process for preparing 3-[(benzamidopiperid-1-yl)alkyl] indoles
US3968142A (en) Hydronaphthalene carboxylic acids and derivatives
IE67059B1 (en) A process for the preparation of a 1,4-dihydropyridine derivative namely (-)-2-{[2-(aminoethoxy)ethoxy]methyl}-4-(2,3-dichlorophenyl)-3-ethoxy-carbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine and its salts
US4639453A (en) Substituted 1-(4-amino-6,7-dialkoxyquinazolinyl)-4 cyclohexenyl derivatives of piperazine and homopiperazine, processes for their preparation and their use, formulations containing these compounds and intermediates