GB1398724A - Disubstituted xanthone carboxylic acid compounds - Google Patents
Disubstituted xanthone carboxylic acid compoundsInfo
- Publication number
- GB1398724A GB1398724A GB4737374A GB4737374A GB1398724A GB 1398724 A GB1398724 A GB 1398724A GB 4737374 A GB4737374 A GB 4737374A GB 4737374 A GB4737374 A GB 4737374A GB 1398724 A GB1398724 A GB 1398724A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- product
- carboxylic acid
- cycloalkyl
- compounds
- 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
- C07D311/78—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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pulmonology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
1398724 Disubstituted xanthone-carboxylic acid compounds SYNTEX (USA) Inc 12 July 1972 [12 Jan 1972 5 June 1972] 47373/74 Divided out of 1398722 Heading C2C The invention comprises compounds of the formula wherein either the X groups are identical and are -S(O) n -R groups where n is 1 or 2 and R is C 1 -C 5 alkyl or C 3 -C 5 cycloalkyl; or one X group is C 1 -C 5 alkyl or alkoxy, or C 3 -C 5 cycloalkyl or cycloalkoxy and the other X group is -S(O) n -R as above; and non-toxic esters, amides and salts thereof. They may be obtained by oxidizing a compound of one of the formulµ wherein R<SP>13</SP>, R<SP>17</SP> and R<SP>19</SP> are C 1 -C 5 alkyl or C 3 -C 5 cycloalkyl, and R<SP>16</SP> and R<SP>18</SP> are C 1 -C 5 alkyl or alkoxy, or C 3 -C 5 cycloalkyl or cycloalkoxy; or an alkyl ester thereof with a peracid or H 2 O 2 optionally followed by hydrolysis, and optionally converting the products into their non-toxic esters, amides or salts. Examples are given for the production of the compounds. Pharmaceutical compositions comprise the compounds of Formula I above which may be administered orally, topically, parenterally or by inhalation in conventional forms, optionally together with other pharmaceutical agents. They are useful for inhibiting the effects of allergic reactions, also as smooth muscle relaxants and as vasodilators. The compounds of formula (5) above are prepared by condensing a o,p-di(alkyl [or cycloalkyl] thio)phenol with a 1,3-dicarboalkoxy-4- halobenzene, in the presence of cuprous oxide, base hydrolysing the product thereof, cyclizing the hydrolysed product, optionally followed by esterification, or by the process which comprises alkylating 5,7 - dimercaptoxanthone - 2 - carboxylic acid optionally followed by hydrolysis, said 5,7 - dimercaptoxanthone - 2 - carboxylic acid being optionally prepared by: condensing o,p - dimethoxyphenol with a 1,3 - dicarboalkoxy - 4 - halobenzene, base hydrolysing the product thereof, cyclizing the hydrolysed product, hydrolysing the cyclized product to give the corresponding 5,7-dihydroxy-xanthone-2- carboxylic acid, esterifying the latter, treating the ester with a dialkylthiocarbamoyl chloride; rearranging the product thereof, base hydrolysing the rearranged product to give the 5,7- dimercaptoxanthone - 2 - carboxylic acid and treating the latter with chlorine under acidic conditions or by reducing 5,7-dimercaptoxanthone-2-carboxylic acid to the corresponding xanthene compound, treating the latter with chlorine under acidic conditions followed by oxidation. The compounds of formulµ (24) and (29) above are prepared by condensing a o-alkyl-, cycloalkyl-, cycloalkoxy or -alkoxy-p-(alkylthio)phenol or a o-alkylthio-p-alkyl- or cycloalkoxy-phenol with a 1,3-dicarboalkoxy-4-halobenzene, base hydrolysing the product thereof, and cyclizing the hydrolysed product.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00217287A US3849565A (en) | 1972-01-12 | 1972-01-12 | Disubstituted xanthone carboxylic acid compounds for inhibiting asthma |
| US25985272A | 1972-06-05 | 1972-06-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1398724A true GB1398724A (en) | 1975-06-25 |
Family
ID=26911795
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4737574A Expired GB1398725A (en) | 1972-01-12 | 1972-07-12 | Disubstituted xanthone carboxylic acid compounds |
| GB4737374A Expired GB1398724A (en) | 1972-01-12 | 1972-07-12 | Disubstituted xanthone carboxylic acid compounds |
| GB4736974A Expired GB1398723A (en) | 1972-01-12 | 1972-07-12 | Chlorosulphonyl-xanthone-2-carboxylic acids |
| GB3253472A Expired GB1398722A (en) | 1972-01-12 | 1972-07-12 | Disbustistuted xanthone carboxylic acid compounds |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4737574A Expired GB1398725A (en) | 1972-01-12 | 1972-07-12 | Disubstituted xanthone carboxylic acid compounds |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4736974A Expired GB1398723A (en) | 1972-01-12 | 1972-07-12 | Chlorosulphonyl-xanthone-2-carboxylic acids |
| GB3253472A Expired GB1398722A (en) | 1972-01-12 | 1972-07-12 | Disbustistuted xanthone carboxylic acid compounds |
Country Status (15)
| Country | Link |
|---|---|
| JP (4) | JPS5347107B2 (en) |
| AR (5) | AR202889A1 (en) |
| AT (2) | AT327897B (en) |
| AU (1) | AU465362B2 (en) |
| BE (1) | BE793749A (en) |
| CA (1) | CA1014167A (en) |
| CH (4) | CH586694A5 (en) |
| DE (1) | DE2265054A1 (en) |
| ES (6) | ES404790A1 (en) |
| FR (1) | FR2167490B1 (en) |
| GB (4) | GB1398725A (en) |
| IL (1) | IL39891A (en) |
| NL (1) | NL7209629A (en) |
| NO (3) | NO137199C (en) |
| SE (1) | SE387946B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE1010719A3 (en) | 1996-10-28 | 1998-12-01 | Dsm Nv | Process for the preparation of hydroxylammonium. |
Family Cites Families (1)
| 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 BE793749D patent/BE793749A/en unknown
-
1972
- 1972-07-12 NL NL7209629A patent/NL7209629A/xx not_active Application Discontinuation
- 1972-07-12 CH CH1177576A patent/CH586694A5/xx not_active IP Right Cessation
- 1972-07-12 CH CH1177376A patent/CH586692A5/xx not_active IP Right Cessation
- 1972-07-12 IL IL39891A patent/IL39891A/en unknown
- 1972-07-12 GB GB4737574A patent/GB1398725A/en not_active Expired
- 1972-07-12 ES ES404790A patent/ES404790A1/en not_active Expired
- 1972-07-12 AR AR243026A patent/AR202889A1/en active
- 1972-07-12 AU AU44458/72A patent/AU465362B2/en not_active Expired
- 1972-07-12 AT AT860574*7A patent/AT327897B/en not_active IP Right Cessation
- 1972-07-12 FR FR7225352A patent/FR2167490B1/fr not_active Expired
- 1972-07-12 GB GB4737374A patent/GB1398724A/en not_active Expired
- 1972-07-12 JP JP6985272A patent/JPS5347107B2/ja not_active Expired
- 1972-07-12 NO NO2495/72A patent/NO137199C/en unknown
- 1972-07-12 GB GB4736974A patent/GB1398723A/en not_active Expired
- 1972-07-12 AT AT860674*7A patent/AT327898B/en not_active IP Right Cessation
- 1972-07-12 CH CH1177476A patent/CH586693A5/xx not_active IP Right Cessation
- 1972-07-12 CH CH1045772A patent/CH588483A5/xx not_active IP Right Cessation
- 1972-07-12 DE DE19722265054 patent/DE2265054A1/en active Pending
- 1972-07-12 GB GB3253472A patent/GB1398722A/en not_active Expired
- 1972-07-12 SE SE7209197A patent/SE387946B/en unknown
-
1973
- 1973-01-01 AR AR249068A patent/AR208274A1/en active
- 1973-03-19 NO NO1092/73A patent/NO137204C/en unknown
- 1973-03-19 NO NO1091/73A patent/NO137203C/en unknown
- 1973-07-13 AR AR249071A patent/AR202188A1/en active
-
1974
- 1974-11-14 CA CA213,708A patent/CA1014167A/en not_active Expired
-
1975
- 1975-01-01 AR AR259804A patent/AR206878A1/en active
- 1975-01-01 AR AR258182A patent/AR206919A1/en active
- 1975-01-03 ES ES433553A patent/ES433553A1/en not_active Expired
- 1975-01-03 ES ES433554A patent/ES433554A1/en not_active Expired
- 1975-01-03 ES ES433555A patent/ES433555A1/en not_active Expired
- 1975-01-03 ES ES433552A patent/ES433552A1/en not_active Expired
- 1975-02-26 ES ES435108A patent/ES435108A1/en not_active Expired
-
1977
- 1977-06-01 JP JP6457077A patent/JPS5350170A/en active Pending
- 1977-06-01 JP JP6457277A patent/JPS5350172A/en active Pending
- 1977-06-01 JP JP6457177A patent/JPS5350171A/en active Pending
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 429A | Application made for amendment of specification (sect. 29/1949) | ||
| 429H | Application (made) for amendment of specification now open to opposition (sect. 29/1949) | ||
| 429D | Case decided by the comptroller ** specification amended (sect. 29/1949) | ||
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |