CA2105707A1 - Substituted cyclohexane derivatives for the treatment of diseases - Google Patents

Substituted cyclohexane derivatives for the treatment of diseases

Info

Publication number
CA2105707A1
CA2105707A1 CA002105707A CA2105707A CA2105707A1 CA 2105707 A1 CA2105707 A1 CA 2105707A1 CA 002105707 A CA002105707 A CA 002105707A CA 2105707 A CA2105707 A CA 2105707A CA 2105707 A1 CA2105707 A1 CA 2105707A1
Authority
CA
Canada
Prior art keywords
glucose
alkyl
phenyl
solution
preparation
Prior art date
Legal status (The legal status 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 status listed.)
Abandoned
Application number
CA002105707A
Other languages
English (en)
French (fr)
Inventor
Horst Hemmerle
Peter Schindler
Roland Utz
Robert Rippel
Andreas Herling
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2105707A1 publication Critical patent/CA2105707A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/36—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/013—Esters of alcohols having the esterified hydroxy group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/55—Acids; Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/383—Cycloaliphatic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4018—Esters of cycloaliphatic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Diabetes (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Emergency Medicine (AREA)
  • Epidemiology (AREA)
  • Obesity (AREA)
  • Endocrinology (AREA)
  • Hematology (AREA)
  • Pulmonology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Transceivers (AREA)
  • Mobile Radio Communication Systems (AREA)
  • Pyridine Compounds (AREA)
CA002105707A 1992-09-09 1993-09-08 Substituted cyclohexane derivatives for the treatment of diseases Abandoned CA2105707A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4230156 1992-09-09
DEP4230156.4 1992-09-09

Publications (1)

Publication Number Publication Date
CA2105707A1 true CA2105707A1 (en) 1994-03-10

Family

ID=6467599

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002105707A Abandoned CA2105707A1 (en) 1992-09-09 1993-09-08 Substituted cyclohexane derivatives for the treatment of diseases

Country Status (22)

Country Link
US (1) US5451573A (enExample)
EP (1) EP0587087B1 (enExample)
JP (1) JPH06211737A (enExample)
KR (1) KR100299205B1 (enExample)
CN (1) CN1042329C (enExample)
AT (1) ATE181237T1 (enExample)
AU (1) AU662836B2 (enExample)
CA (1) CA2105707A1 (enExample)
CZ (1) CZ284995B6 (enExample)
DE (1) DE59309649D1 (enExample)
DK (1) DK0587087T3 (enExample)
ES (1) ES2135429T3 (enExample)
FI (1) FI933902A7 (enExample)
GR (1) GR3030953T3 (enExample)
HU (1) HUT64843A (enExample)
IL (1) IL106935A (enExample)
NO (1) NO179671C (enExample)
PH (1) PH30278A (enExample)
PL (1) PL300328A1 (enExample)
RU (1) RU2131248C1 (enExample)
TW (1) TW255880B (enExample)
ZA (1) ZA936610B (enExample)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4404848A1 (de) * 1994-02-16 1995-08-17 Hoechst Ag Substituierte Cyclohexanolester, ihre Verwendung zur Behandlung von Krankheiten und pharmazeutische Präparate
DE4408082A1 (de) * 1994-03-10 1995-09-14 Hoechst Ag Substituierte Propan-Derivate, Verfahren zu ihrer Herstellung und die Anwendung der Verbindungen zur Behandlung von Krankheiten
DE4416433A1 (de) * 1994-05-10 1995-11-16 Hoechst Ag Cyclohexan-Derivate, Verfahren zu ihrer Herstellung und die Verwendung der Verbindungen zur Behandlung von Krankheiten
AR012449A1 (es) * 1997-04-18 2000-10-18 Hoechst Marion Roussell Deutschland Gmbh Kodaistatinas a, b, c y d, proceso para su produccion, y su uso.
JP4810558B2 (ja) * 1997-08-08 2011-11-09 江崎グリコ株式会社 リン酸化糖およびその製造方法
DE19740080A1 (de) * 1997-09-12 1999-03-18 Hoechst Marion Roussel De Gmbh Neue Phthalaldehyd-Derivate, Verfahren zu deren Herstellung und deren Verwendung
BR9912200A (pt) * 1998-06-24 2001-11-20 Aventis Pharma Gmbh Mumbaistatina, processo para sua produção e seuuso como produto farmacêutico
EP1248763B1 (en) * 1999-10-25 2014-06-25 Sanofi-Aventis Deutschland GmbH Aromatic di-keto derivatives as glucose-6-phosphate translocase inhibitors
PE20021091A1 (es) * 2001-05-25 2003-02-04 Aventis Pharma Gmbh Derivados de fenilurea sustituidos con carbonamida y procedimiento para su preparacion
AU2005250487B2 (en) 2004-06-03 2012-03-29 Eisai R&D Management Co., Ltd Intermediates for the preparation of analogs of halichondrin B
CN101010276B (zh) * 2004-07-26 2011-01-12 中外制药株式会社 环己烷衍生物、其前体药物及其盐、以及含有它的糖尿病治疗药
EP2200992B1 (en) 2007-10-03 2014-02-26 Eisai R&D Management Co., Ltd. Intermediates and methods for the synthesis of halichondrin b analogs
JP6001857B2 (ja) 2008-04-04 2016-10-05 エーザイ・アール・アンド・ディー・マネジメント株式会社 ハリコンドリンｂ類似体
US20100112098A1 (en) * 2008-10-31 2010-05-06 Naturex, S.A. Effects of a decaffeinated green coffee extract on body weight control by regulation of glucose metabolism
BR112012018232B8 (pt) 2010-01-26 2023-01-10 Eisai R&D Man Co Ltd Compostos derivados de furo [3,2-b] pirano úteis na síntese de análogos de halicondrina b e métodos de sintetização de er-80402 e de eribulina
RU2710545C2 (ru) 2013-11-04 2019-12-27 Эйсай Ар Энд Ди Менеджмент Ко., Лтд. Реакции макроциклизации и промежуточные соединения и другие фрагменты, пригодные в получении аналогов халихондрина b
MX384292B (es) 2013-12-06 2025-03-14 Eisai R&D Man Co Ltd Metodos utiles en la sintesis de analogos de halicondrina b.
RU2739034C2 (ru) 2015-05-07 2020-12-21 Эйсай Ар Энд Ди Менеджмент Ко., Лтд. Реакции макроциклизации и промежуточное соединение и другие фрагменты, полезные в синтезе макролидов галихондринов
KR20180107243A (ko) 2016-02-12 2018-10-01 에자이 알앤드디 매니지먼트 가부시키가이샤 에리불린의 합성에서의 중간체 및 관련된 합성 방법
US11136335B2 (en) 2016-06-30 2021-10-05 Eisai R&D Management Co., Ltd. Prins reaction and intermediates useful in the synthesis of halichondrin macrolides and analogs thereof
EP3737673B1 (en) 2018-01-03 2024-03-06 Eisai R&D Management Co., Ltd. Process for preparing halichondrin macrolides and analogs thereof by a prins reaction, and intermediates of this process

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60192555A (ja) * 1984-03-13 1985-10-01 Osaka Chem Lab 抗アレルギ−食品
JPS60243016A (ja) * 1984-05-17 1985-12-03 Tsumura Juntendo Inc 抗インフルエンザウイルス剤
EP0464858A1 (en) * 1984-05-23 1992-01-08 Green Cross Corporation A lipoxygenase inhibitor
DE3603576A1 (de) * 1986-02-06 1987-08-13 Code Kaffee Handel Verwendung von gerbstoffen und/oder chlorogensaeure sowie nahrungs-, genuss- und/oder arzneimittel mit gerbstoff- und/oder chlorogensaeurezusatz

Also Published As

Publication number Publication date
NO179671B (no) 1996-08-19
CN1042329C (zh) 1999-03-03
TW255880B (enExample) 1995-09-01
KR940006580A (ko) 1994-04-25
NO179671C (no) 1996-11-27
DK0587087T3 (da) 1999-12-06
JPH06211737A (ja) 1994-08-02
GR3030953T3 (en) 1999-11-30
NO933201D0 (no) 1993-09-08
HUT64843A (en) 1994-03-28
HU9302527D0 (en) 1993-11-29
RU2131248C1 (ru) 1999-06-10
HK1011934A1 (en) 1999-07-23
IL106935A (en) 1997-07-13
CZ284995B6 (cs) 1999-04-14
CN1086806A (zh) 1994-05-18
NO933201L (no) 1994-03-10
PL300328A1 (en) 1994-03-21
US5451573A (en) 1995-09-19
KR100299205B1 (ko) 2001-11-22
ZA936610B (en) 1994-03-28
EP0587087A1 (de) 1994-03-16
ATE181237T1 (de) 1999-07-15
FI933902A0 (fi) 1993-09-07
CZ186793A3 (en) 1994-03-16
PH30278A (en) 1997-02-20
AU662836B2 (en) 1995-09-14
EP0587087B1 (de) 1999-06-16
IL106935A0 (en) 1993-12-28
DE59309649D1 (de) 1999-07-22
AU4617093A (en) 1994-03-17
FI933902L (fi) 1994-03-10
FI933902A7 (fi) 1994-03-10
ES2135429T3 (es) 1999-11-01

Similar Documents

Publication Publication Date Title
CA2105707A1 (en) Substituted cyclohexane derivatives for the treatment of diseases
US4931458A (en) Heterocyclic rodenticidal compounds, compositions containing the compounds, and methods of use
RU2126378C1 (ru) Замещенные производные циклогексана
US5166171A (en) 6-phenoxymethyl-4-hydroxytetrahydropyran-2-ones and 6-thiphenoxymethyl-4-hydroxytetrahydropyran-2-ones and the corresponding dihydroxycarboxylic acid derivatives, salts and esters, and in treating hypercholesterolemia
NO152091B (no) Analogifremgangsmaate ved fremstilling av antiinflammatorisk virksomme 5-substituerte 2,3-difenylthiofener
US4220648A (en) Antidiabetic 1,2-dihydro-2-oxo-6-neopentyl-nicotinic acids
EP1742927B1 (en) Butanoic acid derivatives, processes for the preparation thereof, pharmaceutical compositions comprising them, and therapeutic applications threreof
Hiebl et al. Synthesis, antiretrovirus effects and phosphorylation kinetics of 3'-isocyano-3'-deoxythymidine and 3'-isocyano-2', 3'-dideoxyuridine
US4219483A (en) 4-Pyrone prostaglandin antagonists
AU2014237600A1 (en) Bicyclic pyrrole derivatives useful as agonists of GPR120
CA1290335C (en) Pharmaceutical compounds
US4275069A (en) Anti-diabetic 1,2-dihydro-2-oxo-6-alkyl-nicotinic acids
PL112931B1 (en) Process for preparing novel 1,5-substituted derivativesof pyrrolidone
US4579585A (en) N'-[4-(1-Fluoromethyl-ethyl)phenyl]-urea derivatives
US4308209A (en) β-Lactones of 2-hydroxy-cyclopentane-carboxylic acids
US4021450A (en) Thiophene derivatives and their preparation
US4454336A (en) Derivatives of 3-(formylmethylthio)-propanoate
US4501894A (en) Heterocyclic alcohols and their derivatives
JPS6232760B2 (enExample)
US4151187A (en) Intermediates for prostaglandin synthesis
US4853401A (en) Spiro-hydantoins as aldose reductase inhibitors
JPH06279439A (ja) 新規化合物及びその製造法
US4058619A (en) Thiophene derivatives having antilipolytic activity
IE63298B1 (en) Novel 6-phenoxymethyl-4-hydroxytetrahydropyran-2-ones and 6-thiophenoxymethyl-4-hydroxytetrahydropyran-2-ones and the corresponding dihydroxycarboxylic acid derivatives,salts and esters,processes for the preparation of these compounds,their use as pharmaceuticals,pharmaceutical preparations and novel phenols and thiophenols
CA1268472A (en) Intermediates for the preparation of pyrrolidine derivatives

Legal Events

Date Code Title Description
EEER Examination request
FZDE Discontinued