GB1398096A – Substituted xanthone carboxylic acid compounds
– Google Patents
GB1398096A – Substituted xanthone carboxylic acid compounds
– Google Patents
Substituted xanthone carboxylic acid compounds
Info
Publication number
GB1398096A
GB1398096A
GB3253172A
GB3253172A
GB1398096A
GB 1398096 A
GB1398096 A
GB 1398096A
GB 3253172 A
GB3253172 A
GB 3253172A
GB 3253172 A
GB3253172 A
GB 3253172A
GB 1398096 A
GB1398096 A
GB 1398096A
Authority
GB
United Kingdom
Prior art keywords
give
xanthone
carboxylic acid
cycloalkylthio
alkylthio
Prior art date
1971-08-23
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
GB3253172A
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.)
Syntex USA LLC
Original Assignee
Syntex USA LLC
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.)
1971-08-23
Filing date
1972-07-12
Publication date
1975-06-18
1972-07-12
Application filed by Syntex USA LLC
filed
Critical
Syntex USA LLC
1975-06-18
Publication of GB1398096A
publication
Critical
patent/GB1398096A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
Classifications
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
A61K31/33—Heterocyclic compounds
A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
A—HUMAN NECESSITIES
A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
A61P37/00—Drugs for immunological or allergic disorders
A61P37/08—Antiallergic agents
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
C07D311/78—Ring systems having three or more relevant rings
C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
C07D311/82—Xanthenes
C07D311/84—Xanthenes 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 in position 9
C07D311/86—Oxygen atoms, e.g. xanthones
Abstract
1398096 Xanthone carbozylic acids SYNTEX (USA) Inc 12 July 1972 [23 Aug 1971] 32531/72 Heading C2C The invention comprises compounds of the formula wherein one X is H and the other is in which n is 1 or 2 and R is lower alkyl or cycloalkyl; and pharmaceutically acceptable, non-toxic esters, amides and salts thereof. They may be obtained by (1) oxidizing a 5- or 7-(alkylthio or cycloalkylthio)-xanthone-2-carboxylic acid or an ester thereof with peracid, optionally followed by hydrolysis to give the corresponding 5- or 7-alkylsulphinyl- or cycloalkylsulphinyl – xanthone – 2 – carboxylic acids or the alkyl esters thereof; or (2) oxidizing a 5- or 7-(alkylthio- or cycloalkylthio)-xanthone- 2-carboxylic acid or an ester thereof with H 2 O 2 , optionally followed by hydrolysis to give the corresponding 5- or 7-alkylsulphonyl- or cycloalkylsulphonyl – xanthone – 2 – carboxylic acids or the alkyl esters thereof, or (3) optionally converting a product of steps (1) or (2) to its corresponding pharmaceutically acceptable, non-toxic ester, amide or salt. Examples are given for the preparation of these compounds. Compounds of the above formula are useful for inhibiting the effects of allergic reactions, also as smooth muscle relaxants and as vasodilators. The compositions containing these compounds optionally together with other pharmaceutical agents, e.g. antibiotics and hormonal agents, may be administered orally, topically, parenterally, or by inhalation and in the form of either solid, liquid or gaseous doses including tablets, suspensions and aerosols. The 5- or 7-(alkylthio- or cycloalkylthio)- xanthone-2-carboxylic acids or esters thereof may be obtained by a process which comprises (1) condensing an o- or p-(alkylthio or cycloalkylthio)phenol with a 1,3-dicarboalkoxy- or dicarbocycloalkoxy-4-halobenzene in the presence of Cu 2 O to give the corresponding 1,3- dicarboalkoxy or dicarbocycloalkoxy-4-(o- or p-alkylthio- or cycloalkylthio-phenyloxy)-benzene, base hydrolysing the latter to give the corresponding 1,3-dicarboxy-4-(o- or p-alkylthio- or cycloalkylthio-phenyloxy)-benzene, and cyclizing the latter to give the corresponding 5- or 7-(alkylthio- or cycloalkylthio)-xanthone- 2-carboxylic acid; or (2) condensing a o- or psubstituted phenol wherein the substituent is OH, (C 1 -C 5 )alkoxy or cycloalkoxy with a 1,3- dicarboalkoxy or dicarbocycloalkoxy-4-halobenzene in the presence of Cu 2 O to give the corresponding 1,3-dicarboalkoxy- or dicarbocycloalkoxy-4-(o- or p-substituted phenyloxy)- benzene, base hydrolysing the latter to give the corresponding 1,3-dicarboxy-4-(o- or p-substituted phenyloxy)-benzene, and cyclizing the latter to give the corresponding 5- or 7-substituted xanthone-2-carboxylic acid; or (3) condensing a o- or p-substituted phenol wherein the substituent is as in (2) with a 1,3-dimethyl- 4-halobenzene to give the corresponding 1,3- dimethyl-4-(o- or p-substituted phenyloxy)- benzene, oxidizing the latter to give the corresponding 1,3-dicarboxy-4-(o- or psubstituted phenyloxy)-benzene, and cyclizing the latter to give the corresponding 5- or 7-substituted xanthone-2-carboxylic acid; and (4) converting any 5- or 7-(C 1 -C 5 )alkoxy or cycloalkoxy xanthone-2-carboxylic acid of steps (2) and (3) to the corresponding 5- or 7-hydroxy compound; and (5) converting any 5- or 7-hydroxy-xanthone-2-carboxylic acid of steps (2), (3) and (4) to its (C 1 -C 5 )alkyl or cycloalkyl ester; and (6) treating a 5- or 7-hydroxy-xanthone-2-carboxylic acid ester of step (5) with a dialkylthiocarbamyl chloride in the presence of a base, rearranging the product thereof, and base hydrolysing the rearranged product thereof to give the corresponding 5- or 7-mercaptoxanthone-2-carboxylic acids; and (7) treating a product of step (6) with an alkyl halide in the presence of base optionally followed by hydrolysis to give the required compounds.
GB3253172A
1971-08-23
1972-07-12
Substituted xanthone carboxylic acid compounds
Expired
GB1398096A
(en)
Applications Claiming Priority (1)
Application Number
Priority Date
Filing Date
Title
US00174261A
US3801598A
(en)
1971-08-23
1971-08-23
Substituted xanthone carboxylic acid compounds
Publications (1)
Publication Number
Publication Date
GB1398096A
true
GB1398096A
(en)
1975-06-18
Family
ID=22635489
Family Applications (4)
Application Number
Title
Priority Date
Filing Date
GB4069974A
Expired
GB1398100A
(en)
1971-08-23
1972-07-12
Preparation of xanthone carboxylic acid derivatives
GB3851574A
Expired
GB1398099A
(en)
1971-08-23
1972-07-12
Substituted xanthone carboxylic acid compounds
GB3253172A
Expired
GB1398096A
(en)
1971-08-23
1972-07-12
Substituted xanthone carboxylic acid compounds
GB3831474A
Expired
GB1398098A
(en)
1971-08-23
1972-07-12
Chlorosulphonylxanthone carboxylic acids
Family Applications Before (2)
Application Number
Title
Priority Date
Filing Date
GB4069974A
Expired
GB1398100A
(en)
1971-08-23
1972-07-12
Preparation of xanthone carboxylic acid derivatives
GB3851574A
Expired
GB1398099A
(en)
1971-08-23
1972-07-12
Substituted xanthone carboxylic acid compounds
Family Applications After (1)
Application Number
Title
Priority Date
Filing Date
GB3831474A
Expired
GB1398098A
(en)
1971-08-23
1972-07-12
Chlorosulphonylxanthone carboxylic acids
Country Status (21)
Country
Link
US
(2)
US3801598A
(en)
JP
(2)
JPS5344472B2
(en)
AR
(3)
AR206284A1
(en)
AT
(3)
AT320644B
(en)
AU
(1)
AU470740B2
(en)
BE
(1)
BE787843A
(en)
CA
(2)
CA1023752A
(en)
CH
(1)
CH585218A5
(en)
DE
(3)
DE2265113C3
(en)
DK
(2)
DK52675A
(en)
ES
(6)
ES404788A1
(en)
FI
(2)
FI780958A
(en)
FR
(1)
FR2150308B1
(en)
GB
(4)
GB1398100A
(en)
HK
(1)
HK26576A
(en)
IL
(1)
IL39885A
(en)
MY
(1)
MY7600087A
(en)
NL
(1)
NL7209618A
(en)
NO
(4)
NO137198C
(en)
SE
(2)
SE387944B
(en)
ZA
(1)
ZA724754B
(en)
Families Citing this family (6)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US3919211A
(en)
*
1973-02-12
1975-11-11
American Home Prod
9-Oxoxanthene-N,N{40 -bis(substituted)-2,7-disulfonamides
IL47519A
(en)
*
1974-07-09
1979-03-12
Roussel Uclaf
7-sulphinimidoyl(sulphimidoyl)-xanthone-2-carboxylic acid derivatives, their preparation and pharmaceutical compositions containing them
US4232040A
(en)
*
1978-03-08
1980-11-04
Syntex (U.S.A.) Inc.
Compositions for and a method of preventing diabetic complications
US4250097A
(en)
*
1978-03-08
1981-02-10
Syntex (U.S.A.) Inc.
Compositions for and a method of preventing diabetic complications
JPS5996856U
(en)
*
1982-12-20
1984-06-30
日本電気株式会社
solid-state imaging device
AU2014233555B2
(en)
*
2007-05-10
2016-11-03
Dogwood Pharmaceuticals, Inc.
Derivatives of fluorene, anthracene, xanthene, dibenzosuberone and acridine and uses thereof
Family Cites Families (1)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
BE759292A
(en)
*
1969-11-27
1971-05-24
Allen & Hanburys Ltd
XANTHONE DERIVATIVES, THEIR PREPARATION AND THEIR USE
0
BE
BE787843D
patent/BE787843A/en
unknown
1971
1971-08-23
US
US00174261A
patent/US3801598A/en
not_active
Expired – Lifetime
1972
1972-01-01
AR
AR243025A
patent/AR206284A1/en
active
1972-07-12
GB
GB4069974A
patent/GB1398100A/en
not_active
Expired
1972-07-12
DE
DE2265113A
patent/DE2265113C3/en
not_active
Expired
1972-07-12
AU
AU44457/72A
patent/AU470740B2/en
not_active
Expired
1972-07-12
DE
DE2234255A
patent/DE2234255C3/en
not_active
Expired
1972-07-12
DE
DE19722265052
patent/DE2265052A1/en
active
Pending
1972-07-12
IL
IL39885A
patent/IL39885A/en
unknown
1972-07-12
CA
CA146,891A
patent/CA1023752A/en
not_active
Expired
1972-07-12
NL
NL7209618A
patent/NL7209618A/xx
not_active
Application Discontinuation
1972-07-12
JP
JP6984372A
patent/JPS5344472B2/ja
not_active
Expired
1972-07-12
ES
ES404788A
patent/ES404788A1/en
not_active
Expired
1972-07-12
FR
FR7225354A
patent/FR2150308B1/fr
not_active
Expired
1972-07-12
ZA
ZA724754A
patent/ZA724754B/en
unknown
1972-07-12
NO
NO72494A
patent/NO137198C/en
unknown
1972-07-12
GB
GB3851574A
patent/GB1398099A/en
not_active
Expired
1972-07-12
AT
AT599472A
patent/AT320644B/en
not_active
IP Right Cessation
1972-07-12
CH
CH1045472A
patent/CH585218A5/xx
not_active
IP Right Cessation
1972-07-12
GB
GB3253172A
patent/GB1398096A/en
not_active
Expired
1972-07-12
GB
GB3831474A
patent/GB1398098A/en
not_active
Expired
1972-07-12
AT
AT95274A
patent/AT325612B/en
not_active
IP Right Cessation
1972-07-12
AT
AT95174A
patent/AT325043B/en
not_active
IP Right Cessation
1972-07-14
SE
SE7209194A
patent/SE387944B/en
unknown
1973
1973-03-19
NO
NO1090/73A
patent/NO137202C/en
unknown
1973-03-19
NO
NO1089/73A
patent/NO137201C/en
unknown
1973-07-30
AR
AR249337A
patent/AR201284A1/en
active
1973-07-30
AR
AR249336A
patent/AR218596A1/en
active
1973-11-08
US
US413979A
patent/US3891766A/en
not_active
Expired – Lifetime
1974
1974-11-14
CA
CA213,670A
patent/CA1011747A/en
not_active
Expired
1975
1975-02-13
DK
DK52675*BA
patent/DK52675A/da
unknown
1975-03-12
ES
ES435558A
patent/ES435558A1/en
not_active
Expired
1975-03-12
ES
ES435555A
patent/ES435555A1/en
not_active
Expired
1975-03-12
ES
ES435556A
patent/ES435556A1/en
not_active
Expired
1975-03-12
ES
ES435559A
patent/ES435559A1/en
not_active
Expired
1975-03-12
ES
ES435557A
patent/ES435557A1/en
not_active
Expired
1975-09-29
SE
SE7510877A
patent/SE7510877L/en
unknown
1976
1976-05-06
HK
HK265/76*UA
patent/HK26576A/en
unknown
1976-06-04
DK
DK247676A
patent/DK247676A/en
unknown
1976-09-16
NO
NO76763176A
patent/NO137597C/en
unknown
1976-12-30
MY
MY87/76A
patent/MY7600087A/en
unknown
1977
1977-04-21
JP
JP4631477A
patent/JPS537674A/en
active
Pending
1978
1978-03-29
FI
FI780958A
patent/FI780958A/en
not_active
Application Discontinuation
1978-12-20
FI
FI783924A
patent/FI783924A/en
unknown
Also Published As
Publication number
Publication date
DK247676A
(en)
1976-06-04
DE2234255B2
(en)
1979-06-13
AR201284A1
(en)
1975-02-28
DE2265052A1
(en)
1976-01-08
US3891766A
(en)
1975-06-24
JPS5344472B2
(en)
1978-11-29
FR2150308B1
(en)
1976-07-02
AR218596A1
(en)
1980-06-30
AU4445772A
(en)
1974-01-17
ES435558A1
(en)
1976-12-16
NO137597C
(en)
1978-03-21
CH585218A5
(en)
1977-02-28
BE787843A
(en)
1973-02-22
NO137202C
(en)
1978-01-18
AT325043B
(en)
1975-09-25
FI780958A
(en)
1978-03-29
DE2234255A1
(en)
1973-03-08
NO137198C
(en)
1978-01-18
DE2234255C3
(en)
1980-02-14
ES435556A1
(en)
1976-12-16
JPS4829778A
(en)
1973-04-19
ES435557A1
(en)
1976-12-16
NL7209618A
(en)
1973-02-27
MY7600087A
(en)
1976-12-31
FR2150308A1
(en)
1973-04-06
ES404788A1
(en)
1975-11-16
SE387944B
(en)
1976-09-20
GB1398099A
(en)
1975-06-18
IL39885A
(en)
1976-01-30
FI783924A
(en)
1978-12-20
AT325612B
(en)
1975-10-27
ES435559A1
(en)
1976-12-16
GB1398100A
(en)
1975-06-18
AU470740B2
(en)
1976-03-25
AT320644B
(en)
1975-02-25
SE7510877L
(en)
1975-09-29
ZA724754B
(en)
1974-02-27
ES435555A1
(en)
1977-07-01
US3801598A
(en)
1974-04-02
IL39885A0
(en)
1972-09-28
DE2265113A1
(en)
1976-04-22
NO137202B
(en)
1977-10-10
DE2265113B2
(en)
1979-10-31
CA1011747A
(en)
1977-06-07
JPS537674A
(en)
1978-01-24
CA1023752A
(en)
1978-01-03
NO763176L
(en)
1973-02-26
AR206284A1
(en)
1976-07-15
GB1398098A
(en)
1975-06-18
NO137198B
(en)
1977-10-10
NO137201C
(en)
1978-01-18
NO137201B
(en)
1977-10-10
NO137597B
(en)
1977-12-12
DK52675A
(en)
1975-08-04
HK26576A
(en)
1976-05-14
DE2265113C3
(en)
1980-07-10
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Legal Events
Date
Code
Title
Description
1975-10-29
PS
Patent sealed [section 19, patents act 1949]
1982-02-10
PCNP
Patent ceased through non-payment of renewal fee
