GB1506076A

GB1506076A – Chroman-4-ones
– Google Patents

GB1506076A – Chroman-4-ones
– Google Patents
Chroman-4-ones

Info

Publication number
GB1506076A

GB1506076A
GB32672/76A
GB3267276A
GB1506076A
GB 1506076 A
GB1506076 A
GB 1506076A
GB 32672/76 A
GB32672/76 A
GB 32672/76A
GB 3267276 A
GB3267276 A
GB 3267276A
GB 1506076 A
GB1506076 A
GB 1506076A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
alkyl
dialkylamino
alkoxycarbonyl
aralkyl
Prior art date
1975-08-07
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
GB32672/76A
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.)

Bayer AG

Original Assignee
Bayer 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.)
1975-08-07
Filing date
1976-08-05
Publication date
1978-04-05

1975-08-07
Priority claimed from DE19752535338
external-priority
patent/DE2535338A1/en

1976-03-20
Priority claimed from DE19762611910
external-priority
patent/DE2611910A1/en

1976-08-05
Application filed by Bayer AG
filed
Critical
Bayer AG

1978-04-05
Publication of GB1506076A
publication
Critical
patent/GB1506076A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

Classifications

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07D—HETEROCYCLIC COMPOUNDS

C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 – C07D459/00, C07D463/00, C07D477/00 or C07D489/00

C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 – C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings

C07D491/10—Spiro-condensed systems

A—HUMAN NECESSITIES

A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING

A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds

A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms

A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom

A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings

A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom

A—HUMAN NECESSITIES

A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING

A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds

A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

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

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

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

C07D311/38—2,3-Dihydro derivatives, e.g. isoflavanones

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

C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems

Abstract

1506076 2,3 – Dihydro – 4H – benzo[b]pyran- 4-ones BAYER AG 5 Aug 1976 [7 Aug 1975 27 Feb 1976 20 March 1976] 32672/76 Heading C2C The invention comprises compounds (X), (XI), (XII) and (XIII) and the preparation of compounds (I) by reacting a compound (II) with a carbonyl compound R1COCHR2R3 (III) in the presence of an amine R9NHR10 (IV) or with the corresponding enamine NR9R10-C(R1)=CR2R3 (VIII) or animal CH(R2)(R3)CH(NR9R10) 2 (IX), wherein; in the above formulae R1-R4 are hydrogen or optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, alkoxycarbonyl, carboxyl or aminoalkyl, or R2-R4 are amino or dialkylamino, or R1 and R2 can be joined to form a carbocyclic or heterocyclic ring; R5-R8 are hydrogen, halogen, hydroxyl, nitro, cyano, carboxyl or optionally substituted alkyl, cycloalkyl, aryl, aralkyl, alkoxy, aralkoxy, aryloxy, alkoxycarbonyl, amino, alkylamino, dialkylamino or acylamino ; R9 and R10 are alkyl or may be joined to form, with the nitrogen atom, a ring; m is an integer of 4-12; n is an integer of 1-18; R19 is hydrogen, amino, alkylamino or dialkylamino or a group -COOR20 (where R20 is hydrogen or alkyl) ; R21 is hydrogen or C 1-18 alkyl; R22 is optionally substituted aryl, aralkyl, alkoxycarbonyl or dialkylamino or a group -R24NR25R26 or -COOR27 (where R24 is alkylene; and R25-R27 are hydrogen or alkyl); R23 is hydrogen or alkyl; R28 is C 1-18 alkenyl or C 1-6 carboxyalkyl; R29 is hydrogen or C 1-6 alkyl; R30 is hydrogen or methyl; R31 is hydroxyl, halogen or methyl; and R32 and R33 are hydrogen or methyl. Examples describe the preparation of inter alia, 2,5,7,8-tetromethyl- 6 – hydroxyl – 2 – (41,81,121 – trimethyltridecanyl) chroman – 4 – one (4 – keto – α – tocopherol) and 2,5,7,8 – tetramethyl – 6 – hydroxy – 2 – (41,81,121– trimethyltrideca – 31,71,111 – trienyl)chroman- 4-one (4-keto-a-tocotrienol). The compounds of the invention are stated to have pharmaceutical (vitamin), herbicidal and antioxidant properties.

GB32672/76A
1975-08-07
1976-08-05
Chroman-4-ones

Expired

GB1506076A
(en)

Applications Claiming Priority (2)

Application Number
Priority Date
Filing Date
Title

DE19752535338

DE2535338A1
(en)

1975-08-07
1975-08-07
Substd. chroman (4) ones prodn. – by reacting (2)-hydroxy-acetophenones and ketootkk ketones in presence of sec. amines

DE19762611910

DE2611910A1
(en)

1976-03-20
1976-03-20
Substd. chroman (4) ones prodn. – by reacting (2)-hydroxy-acetophenones and ketootkk ketones in presence of sec. amines

Publications (1)

Publication Number
Publication Date

GB1506076A
true

GB1506076A
(en)

1978-04-05

Family
ID=25769252
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB32672/76A
Expired

GB1506076A
(en)

1975-08-07
1976-08-05
Chroman-4-ones

Country Status (12)

Country
Link

US
(2)

US4479007A
(en)

JP
(1)

JPS5219670A
(en)

AU
(1)

AU505176B2
(en)

CA
(1)

CA1097362A
(en)

CH
(1)

CH619701A5
(en)

DK
(1)

DK355776A
(en)

ES
(1)

ES450536A1
(en)

FR
(1)

FR2320300A1
(en)

GB
(1)

GB1506076A
(en)

IT
(1)

IT1062656B
(en)

NL
(1)

NL7608777A
(en)

SE
(1)

SE425736B
(en)

Cited By (6)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US4515975A
(en)

*

1980-11-24
1985-05-07
Basf Aktiengesellschaft
Chroman derivatives and their preparation

US4782176A
(en)

*

1983-01-24
1988-11-01
Hoffmann-La Roche Inc.
Phenoxycarboxylic acids

EP0543417A1
(en)

*

1991-11-22
1993-05-26
Lipogenics, Incorporated
Tocotrienols and tocotrienol-like compounds and methods for their use

EP0732329A4
(en)

*

1993-12-07
1996-07-24
Koichi Shudo
Chroman derivative

US6187811B1
(en)

1998-10-28
2001-02-13
Lipogenics, Inc.
Methods for treating benign prostatic hyperplasia using tocotrienols

CN110615784A
(en)

*

2019-10-25
2019-12-27
南开大学
Synthesis and application of lactone analogue with flavone skeleton

Families Citing this family (12)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

DK173350B1
(en)

1985-02-26
2000-08-07
Sankyo Co

Thiazolidine derivatives, their preparation and pharmaceutical composition containing them

JPH0193019A
(en)

*

1987-10-01
1989-04-12
Toubu Denki Kk
Protector

AU628331B2
(en)

*

1988-05-06
1992-09-17
Merck Patent Gesellschaft Mit Beschrankter Haftung
Chroman derivatives

JPH0366669A
(en)

*

1989-08-03
1991-03-22
Shionogi & Co Ltd
Heterocyclic compound

ZA93436B
(en)

*

1992-01-24
1993-08-25
Chugai Pharmaceutical Co Ltd
Benzopyran derivatives

GB9807779D0
(en)

*

1998-04-09
1998-06-10
Ciba Geigy Ag
Organic compounds

DE10044091A1
(en)

*

2000-09-07
2002-04-04
Merck Patent Gmbh

chromanone

TW200930291A
(en)

*

2002-04-29
2009-07-16
Bayer Cropscience Ag
Pesticidal heterocycles

EP3016939B1
(en)

*

2013-07-05
2017-03-29
DSM IP Assets B.V.
Formation of chiral 4-chromanones using chiral pyrrolidines in the presence of acids

EP3016942B1
(en)

*

2013-07-05
2017-03-01
DSM IP Assets B.V.
Formation of chiral 4-chromanones using chiral pyrrolidines

EP3016941B1
(en)

2013-07-05
2017-03-22
DSM IP Assets B.V.
Formation of chiral 4-chromanones using chiral pyrrolidines in the presence of ureas or thioureas

JP6365904B2
(en)

*

2013-07-05
2018-08-01
ディーエスエム アイピー アセッツ ビー．ブイ．

Formation of chiral 4-chromanones using chiral pyrrolidines in the presence of phenols or thiophenols

Family Cites Families (16)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US3553093A
(en)

*

1965-03-19
1971-01-05
Xerox Corp
Color photoelectrophoretic imaging process

US3467676A
(en)

*

1967-04-05
1969-09-16
American Home Prod
5-hydroxy-2,2,7-trialkylchroman-4-ones and derivatives

US3706764A
(en)

*

1969-04-16
1972-12-19
Yoshitomi Pharmaceutical
Phenethylaminomethyl-chromanones and- thiochromanones

US3704323A
(en)

*

1969-12-23
1972-11-28
Squibb & Sons Inc
Indane derivatives

FR2081596A1
(en)

*

1970-03-31
1971-12-10
Serdex
3-phenethylamino methyl chromones – as antidepressant psychoanaleptic agents

US3707476A
(en)

*

1970-10-30
1972-12-26
Colgate Palmolive Co
3-alkanol derivatives of 4h(1)benzopyrano(3,4-d)isoxazoles

GB1357633A
(en)

*

1971-03-02
1974-06-26
Beecham Group Ltd
Chromanone basic ether derivatives

US3699128A
(en)

*

1971-05-26
1972-10-17
Warner Lambert Co
3-methylsulfinyl and 3-methylsulfonyl-4-chromanones

JPS4826766A
(en)

*

1972-08-11
1973-04-09

JPS50148341A
(en)

*

1974-04-19
1975-11-27

US4151179A
(en)

*

1975-03-12
1979-04-24
Fisons Limited
2-(4H-1-Benzopyran-6-yl)propionic acids

US4065574A
(en)

*

1975-08-29
1977-12-27
The Upjohn Company
New method for controlling fungi using 4-chromone, 4-chromanone, 4-chromone oxime and 4-chromanone oxime compounds

BR7606195A
(en)

*

1975-09-17
1977-06-14
Cornell Res Foundation Inc

PROCESS TO TREAT INSECTS TO INHIBIT JUVENILE HORMONAL ACTIVITY, AND PROCESS TO PRODUCE A CHROMENE COMPOUND

US4060619A
(en)

*

1976-01-14
1977-11-29
Ayerst Mckenna And Harrison Ltd.
1,4-Dihydro-4-oxo-benzothiopyrano (4,3-b)pyridine-2-carboxylates and derivatives

US4168271A
(en)

*

1977-04-13
1979-09-18
Scm Corporation
Unsaturated vitamin E intermediates–dehydro and didehydro α-tocopherols

US4162326A
(en)

*

1978-09-27
1979-07-24
Stauffer Chemical Company
Insect control agents

1976

1976-08-03
CH
CH991776A
patent/CH619701A5/de
not_active
IP Right Cessation

1976-08-05
CA
CA258,469A
patent/CA1097362A/en
not_active
Expired

1976-08-05
GB
GB32672/76A
patent/GB1506076A/en
not_active
Expired

1976-08-05
SE
SE7608799A
patent/SE425736B/en
unknown

1976-08-05
IT
IT50771/76A
patent/IT1062656B/en
active

1976-08-05
JP
JP51092839A
patent/JPS5219670A/en
active
Pending

1976-08-06
DK
DK355776A
patent/DK355776A/en
not_active
Application Discontinuation

1976-08-06
FR
FR7624181A
patent/FR2320300A1/en
active
Granted

1976-08-06
ES
ES450536A
patent/ES450536A1/en
not_active
Expired

1976-08-06
NL
NL7608777A
patent/NL7608777A/en
not_active
Application Discontinuation

1976-08-09
AU
AU16674/76A
patent/AU505176B2/en
not_active
Expired

1979

1979-07-23
US
US06/059,860
patent/US4479007A/en
not_active
Expired – Lifetime

1982

1982-01-07
US
US06/337,802
patent/US4415741A/en
not_active
Expired – Fee Related

Cited By (16)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US4515975A
(en)

*

1980-11-24
1985-05-07
Basf Aktiengesellschaft
Chroman derivatives and their preparation

US4782176A
(en)

*

1983-01-24
1988-11-01
Hoffmann-La Roche Inc.
Phenoxycarboxylic acids

US6143770A
(en)

*

1991-11-22
2000-11-07
Lipogenics, Inc.
Tocotrienols and tocotrienol-like compounds and methods for their use

EP0543417A1
(en)

*

1991-11-22
1993-05-26
Lipogenics, Incorporated
Tocotrienols and tocotrienol-like compounds and methods for their use

WO1993009777A1
(en)

*

1991-11-22
1993-05-27
Lipogenics, Inc.
Tocotrienols and tocotrienol-like compounds and methods for their use

AU670557B2
(en)

*

1991-11-22
1996-07-25
Lipogenics, Inc.
Tocotrienols and tocotrienol-like compounds and methods for their use

US6239171B1
(en)

1991-11-22
2001-05-29
Lipogenics, Inc.
Tocotrienols and tocotrienol-like compounds and methods for their use

US5591772A
(en)

*

1991-11-22
1997-01-07
Lipogenics, Inc.
Tocotrienols and tocotrienol-like compounds and methods for their use

US6204290B1
(en)

1991-11-22
2001-03-20
Lipogenics, Inc.
Tocotrienols and tocotrienol-like compounds and methods for their use

US5821264A
(en)

*

1991-11-22
1998-10-13
Lipogenics, Inc.
Tocotrienols and tocotrienol-like compounds and methods for their use

EP0732329A4
(en)

*

1993-12-07
1996-07-24
Koichi Shudo
Chroman derivative

US5719180A
(en)

*

1993-12-07
1998-02-17
Koichi Shudo
Chroman derivatives having vitamin E-like activities

EP0732329A1
(en)

*

1993-12-07
1996-09-18
Shudo, Koichi, Prof. Dr.
Chroman derivative

US6187811B1
(en)

1998-10-28
2001-02-13
Lipogenics, Inc.
Methods for treating benign prostatic hyperplasia using tocotrienols

CN110615784A
(en)

*

2019-10-25
2019-12-27
南开大学
Synthesis and application of lactone analogue with flavone skeleton

CN110615784B
(en)

*

2019-10-25
2022-10-25
南开大学
Synthesis and application of lactone analogue with flavone skeleton

Also Published As

Publication number
Publication date

AU1667476A
(en)

1978-02-16

SE7608799L
(en)

1977-02-08

NL7608777A
(en)

1977-02-09

CA1097362A
(en)

1981-03-10

ES450536A1
(en)

1977-11-16

US4415741A
(en)

1983-11-15

FR2320300A1
(en)

1977-03-04

SE425736B
(en)

1982-11-01

AU505176B2
(en)

1979-11-08

IT1062656B
(en)

1984-10-20

FR2320300B1
(en)

1979-07-27

US4479007A
(en)

1984-10-23

JPS5219670A
(en)

1977-02-15

CH619701A5
(en)

1980-10-15

DK355776A
(en)

1977-02-08

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Legal Events

Date
Code
Title
Description

1978-07-19
PS
Patent sealed [section 19, patents act 1949]

1986-04-03
PCNP
Patent ceased through non-payment of renewal fee

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