GB1495189A - 4-oxo-4h-benzopyran derivatives and process for their preparation - Google Patents

4-oxo-4h-benzopyran derivatives and process for their preparation

Info

Publication number
GB1495189A
GB1495189A GB37553/75A GB3755375A GB1495189A GB 1495189 A GB1495189 A GB 1495189A GB 37553/75 A GB37553/75 A GB 37553/75A GB 3755375 A GB3755375 A GB 3755375A GB 1495189 A GB1495189 A GB 1495189A
Authority
GB
United Kingdom
Prior art keywords
formula
optionally substituted
alkyl
hydrogen
oxo
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.)
Expired
Application number
GB37553/75A
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.)
Pfizer Ltd
Original Assignee
Pfizer Ltd
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 Pfizer Ltd filed Critical Pfizer Ltd
Priority to GB37553/75A priority Critical patent/GB1495189A/en
Priority to DE19762640617 priority patent/DE2640617A1/en
Priority to JP51108684A priority patent/JPS5257182A/en
Priority to BE170560A priority patent/BE846109A/en
Priority to DK411976A priority patent/DK411976A/en
Priority to FR7627339A priority patent/FR2329269A1/en
Priority to NL7610059A priority patent/NL7610059A/en
Priority to LU75770A priority patent/LU75770A1/xx
Priority to US05/795,652 priority patent/US4117149A/en
Publication of GB1495189A publication Critical patent/GB1495189A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/116—Heterocyclic compounds
    • A23K20/121—Heterocyclic compounds containing oxygen or sulfur as hetero atom
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/34—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only
    • C07D311/36—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only not hydrogenated in the hetero ring, e.g. isoflavones

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Husbandry (AREA)
  • Zoology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Food Science & Technology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pyrane Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1495189 Process for preparation of 4-oxo-4H- benzopyrans and some of which are novel PFIZER Ltd 10 Sept 1976 [12 Sept 1975] 37553/75 Heading C2C The invention comprises a process for preparing compounds of the Formula I wherein R<SP>1</SP> is optionally substituted aryl, heteroaryl, cycloalkyl, optionally substituted aralkyl, alkoxy or optionally substituted aryloxy or aryl sulphonyl, R<SP>2</SP> is hydrogen or alkyl and the ring A is optionally substituted with, one or more halogen, hydroxy, alkyl or alkoxy, wherein alkyl groups have 1 to 4 carbon atoms, in which a compound of the Formula II is reacted with an N,N-dialkyl or N-alkyl N-aryl amide of formic or a C 2-5 alkanoic acid and a strong acid chloride in the presence of boron trifluoride etherate, followed in the case where ring A is substituted with one or more hydroxyl groups and an amide of a C 2-5 alkanoic acid is used, by hydrolysis of the resulting o-acylated product. Novel compounds of the Formula I are (1) those in which R 2 is hydrogen, R<SP>1</SP> is 4-isopropylphenyl, 4-bromophenyl, p-tolyl, 3-chlorophenyl, p-biphenyl or 4-methane sulphonylphenyl and A is substituted in the 5- and 7-position by hydroxy, and (ii) those in which R<SP>2</SP> is hydrogen and R<SP>1</SP> and ring A are as in Formula I other than those in which R<SP>1</SP> is phenyl, substituted phenyl or heteroaryl. 5,7 - Diacetyloxy - 3 - p - fluorophenyl - 2- methyl-4-oxo-4H-benzopyran was prepared from the 5,7-dihydroxy compound for identification purposes. Pharmaceutical compositions of the novel compounds I with usual excipients are growth promotors and improve feed efficiency when administered orally or parenterally. Implants, feed additives and feed concentrates are particularly mentioned.
GB37553/75A 1975-09-12 1975-09-12 4-oxo-4h-benzopyran derivatives and process for their preparation Expired GB1495189A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
GB37553/75A GB1495189A (en) 1975-09-12 1975-09-12 4-oxo-4h-benzopyran derivatives and process for their preparation
DE19762640617 DE2640617A1 (en) 1975-09-12 1976-09-09 PROCESS FOR THE PRODUCTION OF 4-OXO-4H-BENZOPYRAN DERIVATIVES, 4-OXO-4H-BENZOPYRAN DERIVATIVES AND THEIR USE IN FEED
JP51108684A JPS5257182A (en) 1975-09-12 1976-09-10 Preparation method of 44oxoo4h benzopyran derivatives
BE170560A BE846109A (en) 1975-09-12 1976-09-10 NEW DERIVATIVES OF 4-OXO-4H-BENZOPYRAN, THEIR PROCESS FOR PREPARATION AND THEIR APPLICATION TO ANIMAL FEEDING
DK411976A DK411976A (en) 1975-09-12 1976-09-10 BENZOPYRANE DERIVATIVES AND THEIR MANUFACTURE AND USE
FR7627339A FR2329269A1 (en) 1975-09-12 1976-09-10 NEW DERIVATIVES OF 4-OXO-4H-BENZOPYRANE, THEIR PREPARATION PROCESS AND THEIR APPLICATION TO ANIMAL FEEDING
NL7610059A NL7610059A (en) 1975-09-12 1976-09-10 PROCESS FOR THE PREPARATION OF 4-OXO-4H-BENZO-PYRAND DERIVATIVES.
LU75770A LU75770A1 (en) 1975-09-12 1976-09-10
US05/795,652 US4117149A (en) 1975-09-12 1977-05-10 4-oxo-4h-benzopyrans as animal growth promotants

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB37553/75A GB1495189A (en) 1975-09-12 1975-09-12 4-oxo-4h-benzopyran derivatives and process for their preparation

Publications (1)

Publication Number Publication Date
GB1495189A true GB1495189A (en) 1977-12-14

Family

ID=10397333

Family Applications (1)

Application Number Title Priority Date Filing Date
GB37553/75A Expired GB1495189A (en) 1975-09-12 1975-09-12 4-oxo-4h-benzopyran derivatives and process for their preparation

Country Status (8)

Country Link
JP (1) JPS5257182A (en)
BE (1) BE846109A (en)
DE (1) DE2640617A1 (en)
DK (1) DK411976A (en)
FR (1) FR2329269A1 (en)
GB (1) GB1495189A (en)
LU (1) LU75770A1 (en)
NL (1) NL7610059A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1210341A1 (en) * 1999-09-06 2002-06-05 Novogen Research Pty. Ltd. Compositions and therapeutic methods involving isoflavones and analogues thereof
US6987098B2 (en) 1992-05-19 2006-01-17 Novogen Research Pty. Ltd. Health supplement
US7033621B1 (en) 1997-04-28 2006-04-25 Novogen, Inc. Isoflavone compositions produced from legumes
US7202273B2 (en) 1996-08-30 2007-04-10 Novogen Research Pty Ltd Therapeutic methods and compositions involving isoflavones
US7312344B2 (en) 2001-03-08 2007-12-25 Novogen Research Pty Limited Dimeric isoflavones
AU2004202747B2 (en) * 1999-09-06 2008-04-24 Novogen Research Pty Ltd Compositions and therapeutic methods involving isoflavones and analogues thereof

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991015483A1 (en) * 1990-04-06 1991-10-17 Chinoin Gyógyszer És Vegyészeti Termékek Gyára Rt An improved process for the preparation of substituted isoflavone derivatives
FR2693724B1 (en) * 1992-07-17 1994-10-07 Lipha Use of benzopyran or benzothiopyran compounds for the induction of the expression of genes for the nodulation of bacteria of the genus Rhizobium associated with legumes.
GB9621757D0 (en) * 1996-10-18 1996-12-11 Ciba Geigy Ag Phenyl-substituted bicyclic heterocyclyl derivatives and their use
US5981775A (en) * 1998-09-16 1999-11-09 Board Of Trustees Operating Michigan State University Process for the preparation of isoflavones
SK14762001A3 (en) * 1999-04-16 2002-10-08 Astrazeneca Ab Estrogen receptor-beta ligands

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6987098B2 (en) 1992-05-19 2006-01-17 Novogen Research Pty. Ltd. Health supplement
US7045155B2 (en) 1992-05-19 2006-05-16 Novogen Research Pty Ltd. Dietary supplements comprising soy hypocotyls containing at least one isoflavone
USRE40792E1 (en) 1992-05-19 2009-06-23 Novogen Research Pty Ltd Health supplements containing phyto-oestrogens, analogues or metabolites thereof
US7202273B2 (en) 1996-08-30 2007-04-10 Novogen Research Pty Ltd Therapeutic methods and compositions involving isoflavones
US7033621B1 (en) 1997-04-28 2006-04-25 Novogen, Inc. Isoflavone compositions produced from legumes
EP1210341A1 (en) * 1999-09-06 2002-06-05 Novogen Research Pty. Ltd. Compositions and therapeutic methods involving isoflavones and analogues thereof
EP1210341A4 (en) * 1999-09-06 2003-06-11 Novogen Res Pty Ltd Compositions and therapeutic methods involving isoflavones and analogues thereof
EP1721903A1 (en) * 1999-09-06 2006-11-15 Novogen Research Pty. Ltd. Compositions and therapeutic methods involving isoflavones and analogues thereof
AU2004202747B2 (en) * 1999-09-06 2008-04-24 Novogen Research Pty Ltd Compositions and therapeutic methods involving isoflavones and analogues thereof
US7488494B2 (en) 1999-09-06 2009-02-10 Novogen Research Pty Ltd. Compositions and therapeutic methods involving isoflavones and analogues thereof
US7312344B2 (en) 2001-03-08 2007-12-25 Novogen Research Pty Limited Dimeric isoflavones

Also Published As

Publication number Publication date
DE2640617A1 (en) 1977-03-17
NL7610059A (en) 1977-03-15
DK411976A (en) 1977-03-13
LU75770A1 (en) 1978-05-12
JPS5257182A (en) 1977-05-11
FR2329269A1 (en) 1977-05-27
BE846109A (en) 1977-03-10

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee