GB1495189A - 4-oxo-4h-benzopyran derivatives and process for their preparation - Google Patents
4-oxo-4h-benzopyran derivatives and process for their preparationInfo
- 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
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)
- Obesity (AREA)
- Medicinal Chemistry (AREA)
- Zoology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Animal Husbandry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Food Science & Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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.
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 |
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 |
LU75770A LU75770A1 (en) | 1975-09-12 | 1976-09-10 | |
JP51108684A JPS5257182A (en) | 1975-09-12 | 1976-09-10 | Preparation method of 44oxoo4h benzopyran derivatives |
DK411976A DK411976A (en) | 1975-09-12 | 1976-09-10 | BENZOPYRANE DERIVATIVES AND THEIR MANUFACTURE AND USE |
NL7610059A NL7610059A (en) | 1975-09-12 | 1976-09-10 | PROCESS FOR THE PREPARATION OF 4-OXO-4H-BENZO-PYRAND 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 |
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)
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU631860B2 (en) * | 1990-04-06 | 1992-12-10 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara | 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 |
CN1358091A (en) * | 1999-04-16 | 2002-07-10 | 阿斯特拉曾尼卡有限公司 | Estrogen receptor-beta ligands |
-
1975
- 1975-09-12 GB GB37553/75A patent/GB1495189A/en not_active Expired
-
1976
- 1976-09-09 DE DE19762640617 patent/DE2640617A1/en not_active Withdrawn
- 1976-09-10 DK DK411976A patent/DK411976A/en unknown
- 1976-09-10 FR FR7627339A patent/FR2329269A1/en not_active Withdrawn
- 1976-09-10 BE BE170560A patent/BE846109A/en unknown
- 1976-09-10 JP JP51108684A patent/JPS5257182A/en active Pending
- 1976-09-10 NL NL7610059A patent/NL7610059A/en not_active Application Discontinuation
- 1976-09-10 LU LU75770A patent/LU75770A1/xx unknown
Cited By (11)
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 |
---|---|
JPS5257182A (en) | 1977-05-11 |
LU75770A1 (en) | 1978-05-12 |
FR2329269A1 (en) | 1977-05-27 |
BE846109A (en) | 1977-03-10 |
NL7610059A (en) | 1977-03-15 |
DK411976A (en) | 1977-03-13 |
DE2640617A1 (en) | 1977-03-17 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PCNP | Patent ceased through non-payment of renewal fee |