GB1138242A - Nitrogen-containing heterocyclic compounds and processes for their production - Google Patents
Nitrogen-containing heterocyclic compounds and processes for their productionInfo
- Publication number
- GB1138242A GB1138242A GB1476366A GB1476366A GB1138242A GB 1138242 A GB1138242 A GB 1138242A GB 1476366 A GB1476366 A GB 1476366A GB 1476366 A GB1476366 A GB 1476366A GB 1138242 A GB1138242 A GB 1138242A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- acid
- give
- group
- phthalide
- 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
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Indole Compounds (AREA)
- Central Air Conditioning (AREA)
Abstract
1,138,242. 1,2,8,9-Tetraazaphenalene derivatives. J. R. GEIGY A.G. 4 April, 1966 [5 April, 1965], No. 14763/66. Heading C2C. Novel compounds of the tautomeric formulµ and acid addition salts thereof, wherein X is O or S, and R 1 is H, C 1-6 alkyl or aryl, may be prepared either by heating a compound of formula wherein R 2 is H or C 1-6 alkyl, one of the radicals A and B is -CHO or a group of equivalent oxidative state, and the other is -COOH or a group of equivalent oxidative state, whereby the two vicinal COOH groups can be linked to form an anhydride or a CHO group can be linked with a vicinal COOH group to form a lactone, with at least two equimolecular amounts of hydrazine hydrate until ring-closure is complete, and if desired converting the OH group of the product to SH by treatment with at least an equimolar amount of P 2 S 5 followed by optional conversion of the OH or SH group to an acid addition salt; or alternatively by heating a compound of the formula wherein R 1 is as defined and R 4 is Cl, Br, OH or C 1-6 alkoxy with at least an equimolar amount of hydrazine hydrate and optionally treating the product with P 2 S 5 and/or an acid as above. 3-Dibromomethylphthalic anhydride is prepared by bromination of 3-methylphthalic anhydride with N-bromosuccinimide. This product is hydrolysed to give 3-hydroxy-7-carboxyphthalide and its tautomer 3-aldehydo-phthalic acid. It is also hydrolysed to give 7-carboxyphthalide, which is subsequently treated with POCl 5 or SOCl 2 to give 7-chlorocarbonyl-phthalide, which is in turn brominated with N-bromosuccinimide to give 7-chlorocarbonyl-3-bromophthalide. 2 - Carbomethoxy - 6 - dibromomethyl - benzoic acid is prepared by bromination of 2-carbomethoxy - 6 - methyl - benzoic acid, which has been itself prepared by esterification of 3-methylphthalic acid. 8 - Carboxy " 1 - (2H) - phthalazinone is prepared by refluxing with hydrazine hydrate either 3 - dibromomethylphthalic anhydride, or 7 - chlorocarbonyl - 3 - bromo - phthalide. Esters of this acid are made either by treatment thereof with a diazoalkane, or by treatment with SOCl 2 , followed by reaction of the intermediate product with an alkanol (EtOH and MeOH exemplified). The ethyl esters of this acid are N-alkylated with Et 2 SO 4 or Me 2 SO 4 . 8 - Carbethoxy - 1(2H) - phthalazinone is prepared by alcoholysing 7-chlorocarbonylphthalide with EtOH to give 7-carbethoxy-phthalide which is then brominated to give 3-bromo-7- carbethoxy phthalide, which is finally reacted with hydrazine hydrate. 2 - Phenyl - 8 - carboxy - 1(2H) - phthalazinone is prepared by reacting phenylhydrazine with 3-hydroxy-7-carboxy-phthalide. Pharmaceutical compositions having hypotensive and sedative action comprise at least one compound of the first formula given above or a physiologically acceptable salt thereof, together with at least one pharmaceutically acceptable inert carrier. They may take the forms of tablets, capsules, suspensions, solutions, syrups, powders &c., and may be administered orally or parenterally.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US44576265A | 1965-04-05 | 1965-04-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1138242A true GB1138242A (en) | 1968-12-27 |
Family
ID=23770102
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1476466A Expired GB1144881A (en) | 1965-04-05 | 1966-04-04 | Tetraazaphenalene compounds and processes for their production |
GB1476266A Expired GB1138753A (en) | 1965-04-05 | 1966-04-04 | Nitrogen-containing heterocyclic compounds and processes for their production |
GB1476366A Expired GB1138242A (en) | 1965-04-05 | 1966-04-04 | Nitrogen-containing heterocyclic compounds and processes for their production |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1476466A Expired GB1144881A (en) | 1965-04-05 | 1966-04-04 | Tetraazaphenalene compounds and processes for their production |
GB1476266A Expired GB1138753A (en) | 1965-04-05 | 1966-04-04 | Nitrogen-containing heterocyclic compounds and processes for their production |
Country Status (12)
Country | Link |
---|---|
AT (3) | AT259568B (en) |
BE (3) | BE679047A (en) |
CH (3) | CH483432A (en) |
DE (3) | DE1695066A1 (en) |
DK (3) | DK119504B (en) |
ES (5) | ES325110A1 (en) |
FR (1) | FR5595M (en) |
GB (3) | GB1144881A (en) |
IL (3) | IL25524A (en) |
NL (3) | NL6604483A (en) |
NO (3) | NO118492B (en) |
SE (6) | SE323689B (en) |
-
1966
- 1966-04-04 GB GB1476466A patent/GB1144881A/en not_active Expired
- 1966-04-04 NL NL6604483A patent/NL6604483A/xx unknown
- 1966-04-04 NO NO162451A patent/NO118492B/no unknown
- 1966-04-04 NL NL6604482A patent/NL6604482A/xx unknown
- 1966-04-04 IL IL2552466A patent/IL25524A/en unknown
- 1966-04-04 AT AT318466A patent/AT259568B/en active
- 1966-04-04 IL IL2552566A patent/IL25525A/en unknown
- 1966-04-04 GB GB1476266A patent/GB1138753A/en not_active Expired
- 1966-04-04 NL NL6604484A patent/NL6604484A/xx unknown
- 1966-04-04 ES ES0325110A patent/ES325110A1/en not_active Expired
- 1966-04-04 DE DE19661695066 patent/DE1695066A1/en active Pending
- 1966-04-04 ES ES0325111A patent/ES325111A1/en not_active Expired
- 1966-04-04 SE SE448766A patent/SE323689B/xx unknown
- 1966-04-04 ES ES0325113A patent/ES325113A1/en not_active Expired
- 1966-04-04 AT AT318566A patent/AT265297B/en active
- 1966-04-04 DE DE19661695065 patent/DE1695065A1/en active Pending
- 1966-04-04 GB GB1476366A patent/GB1138242A/en not_active Expired
- 1966-04-04 NO NO16245066A patent/NO121495B/no unknown
- 1966-04-04 SE SE448566A patent/SE323688B/xx unknown
- 1966-04-04 DE DE19661695064 patent/DE1695064A1/en active Pending
- 1966-04-04 DK DK174666A patent/DK119504B/en unknown
- 1966-04-04 DK DK174866A patent/DK120240B/en unknown
- 1966-04-04 AT AT318366A patent/AT264530B/en active
- 1966-04-04 SE SE448666A patent/SE317387B/xx unknown
- 1966-04-04 ES ES0325112A patent/ES325112A1/en not_active Expired
- 1966-04-04 SE SE1195568A patent/SE318284B/xx unknown
- 1966-04-04 ES ES0325109A patent/ES325109A1/en not_active Expired
- 1966-04-04 IL IL2552666A patent/IL25526A/en unknown
- 1966-04-04 DK DK174766A patent/DK119313B/en unknown
- 1966-04-04 SE SE242470A patent/SE350263B/xx unknown
- 1966-04-04 NO NO16245266A patent/NO118493B/no unknown
- 1966-04-05 CH CH486066A patent/CH483432A/en not_active IP Right Cessation
- 1966-04-05 CH CH486266A patent/CH481122A/en not_active IP Right Cessation
- 1966-04-05 CH CH486166A patent/CH475994A/en not_active IP Right Cessation
- 1966-04-05 BE BE679047D patent/BE679047A/xx unknown
- 1966-04-05 BE BE679046D patent/BE679046A/xx unknown
- 1966-04-05 BE BE679045D patent/BE679045A/xx unknown
- 1966-07-04 FR FR68073A patent/FR5595M/fr not_active Expired
-
1970
- 1970-02-25 SE SE02423/70A patent/SE350262B/xx unknown
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
IE36797B1 (en) | Derivatives of benzodiazepines | |
SU991945A3 (en) | Process for preparing derivatives of mercaptoimidazole or their salts | |
US4188486A (en) | 2-Substituted benzimidazole compounds | |
IE33124B1 (en) | New heterocyclic carboxylic acids their derivatives and use | |
EP0043858B1 (en) | Hetero ring-substituted oxoalkanoic acid derivatives | |
RU2149872C1 (en) | Pyridylthio-compounds for control of helicobacter bacterium | |
JPS62187462A (en) | 5, 6-dialkoxyquinazoline derivative | |
IE37795L (en) | Quinaldamide derivatives | |
US3472848A (en) | 3-hydroxy and 3-mercapto-pyrazinoyl-guanidines,corresponding ethers and thioethers and processes for their preparation | |
SU1456018A3 (en) | Method of producing derivatives of thieno-(2,3-d)-imidazole | |
US3227716A (en) | Therapeutically-active dibenzocycloheptane derivatives | |
IL25448A (en) | 2-nitro-imidazole derivatives and process for the manufacture thereof | |
GB1138242A (en) | Nitrogen-containing heterocyclic compounds and processes for their production | |
US4192880A (en) | 2-Substituted benzimidazole compounds | |
SU1033003A3 (en) | Process for preparing derivatives of 4-pyrimidone or their pharmaceutically acceptable acid addition salts | |
DK156222B (en) | METHOD OF ANALOGY FOR THE PREPARATION OF SUBSTITUTED THIAZOLOOE3,2-AAAPYRIMIDINES OR SALTS OR ISOMERS OR ISOMER MIXTURES THEREOF | |
US5684006A (en) | Isoxazole and pyrazole derivatives as dopamine receptor subtype ligands | |
JPS6191185A (en) | Novel oxadiazolyl-1,4-dihydropyridine derivative | |
JPH0365349B2 (en) | ||
IE37043B1 (en) | Novel pyrimidinones | |
US5763453A (en) | Condensed indan derivatives and salts thereof | |
JPH01319487A (en) | Imidazo(2,1-b)benzothiazole derivative and anti-ulcer agent containing the same derivative as active ingredient | |
PL91000B1 (en) | Process for the manufacture of indole derivatives [gb1407658a] | |
US3390150A (en) | Process for the preparation of 1-(beta-hydroxyethyl)-5-nitroimidazole-2-carboxylic acid gamma-lactone | |
HU176942B (en) | Process for preparing 2,3-disubstituted tetrahydro-pyrrolo!1,2-a!-pyrimidines |