ES308570A1 - New pyridobenzothiadiazepine derivatives and process for producing same - Google Patents
New pyridobenzothiadiazepine derivatives and process for producing sameInfo
- Publication number
- ES308570A1 ES308570A1 ES0308570A ES308570A ES308570A1 ES 308570 A1 ES308570 A1 ES 308570A1 ES 0308570 A ES0308570 A ES 0308570A ES 308570 A ES308570 A ES 308570A ES 308570 A1 ES308570 A1 ES 308570A1
- Authority
- ES
- Spain
- Prior art keywords
- formula
- prepared
- compound
- chlorine
- hydrogen
- 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
- MNIASYGCMZJLPA-UHFFFAOYSA-N pyrido[2,3-i][1,2,3]benzothiadiazepine Chemical class S1N=NC=CC2=C1C1=C(C=C2)N=CC=C1 MNIASYGCMZJLPA-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 3
- -1 methylene dioxy group Chemical group 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 abstract 2
- HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical class OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- LYESTQKHIPXVIK-UHFFFAOYSA-N 4-chloro-2-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1S(Cl)(=O)=O LYESTQKHIPXVIK-UHFFFAOYSA-N 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000005002 aryl methyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000002934 diuretic Substances 0.000 abstract 1
- 230000001882 diuretic effect Effects 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/96—Sulfur atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Novel compounds of the formula <FORM:1048868/C2/1> wherein R1 and R2, in the 7, 8 or 9 position, either independently of each other represent hydrogen, chlorine, bromine, the tri-fluoromethyl group or alkyl or alkoxy radicals containing 1 to 5 carbon atoms or taken together can also represent the methylene dioxy group are prepared by treating compounds of the formula <FORM:1048868/C2/2> wherein R1 and R2 have the above significance with a condensing agent either selected from thionyl chloride, phosphorus pentachloride and phosphorus trichloride when R3 is hydrogen or selected from butyl lithium and sodium hydride when R3 is an aryl, arylmethyl or C1 to C4 alkyl radical. Pharmaceutical compositions having diuretic and hypotensive activity and which may be administered orally contain as the active ingredient at least one compound of the first general-formula above. Substituted pipecolinic acid corresponding to the second general formula above wherein R3 represents hydrogen is prepared by condensing a compound of the formula <FORM:1048868/C2/3> wherein Hal represents chlorine or bromine and R1 and R2 have the above significance with a suitable ester of pipecolinic acid, reducing the nitro group in the resulting 2-nitrobenzenesulphonyl - pipecolinic ester by, for example, catalytic hydrogenation to give the corresponding amino compound which is then saponified to give the desired starting material. 4 - Chloro - 6 - nitrobenzenesulphonyl chloride is prepared by reacting 4,41-dichloro-6,61-dinitrophenyl-disulphide with chlorine gas.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34054264A | 1964-01-27 | 1964-01-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES308570A1 true ES308570A1 (en) | 1965-06-01 |
Family
ID=23333836
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0308570A Expired ES308570A1 (en) | 1964-01-27 | 1965-01-26 | New pyridobenzothiadiazepine derivatives and process for producing same |
| ES0308569A Expired ES308569A1 (en) | 1964-01-27 | 1965-01-26 | Procedure for the preparation of new N-heterociclic compounds. (Machine-translation by Google Translate, not legally binding) |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0308569A Expired ES308569A1 (en) | 1964-01-27 | 1965-01-26 | Procedure for the preparation of new N-heterociclic compounds. (Machine-translation by Google Translate, not legally binding) |
Country Status (7)
| Country | Link |
|---|---|
| AT (2) | AT251590B (en) |
| BE (2) | BE658844A (en) |
| CH (2) | CH443321A (en) |
| ES (2) | ES308570A1 (en) |
| FR (2) | FR4416M (en) |
| GB (2) | GB1048868A (en) |
| NL (3) | NL6500953A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3506646A (en) * | 1966-06-27 | 1970-04-14 | American Home Prod | Process for the preparation of 7h-pyrido (1,2-b)(1,2,5)benzothiadiazepine 5,5 - dioxides and pyrrolo(1,2-b)(1,2,5)benzothiadiazepine 5,5-dioxides |
-
0
- NL NL123600D patent/NL123600C/xx active
-
1964
- 1964-12-31 CH CH1688164A patent/CH443321A/en unknown
- 1964-12-31 CH CH1688064A patent/CH441345A/en unknown
-
1965
- 1965-01-26 ES ES0308570A patent/ES308570A1/en not_active Expired
- 1965-01-26 AT AT65365A patent/AT251590B/en active
- 1965-01-26 GB GB3287/65A patent/GB1048868A/en not_active Expired
- 1965-01-26 NL NL6500953A patent/NL6500953A/xx unknown
- 1965-01-26 ES ES0308569A patent/ES308569A1/en not_active Expired
- 1965-01-26 BE BE658844D patent/BE658844A/xx unknown
- 1965-01-26 GB GB3288/65A patent/GB1048869A/en not_active Expired
- 1965-01-26 BE BE658845D patent/BE658845A/xx unknown
- 1965-01-26 NL NL6500954A patent/NL6500954A/xx unknown
- 1965-01-26 AT AT65465A patent/AT250972B/en active
- 1965-04-24 FR FR14530A patent/FR4416M/fr not_active Expired
- 1965-04-24 FR FR14529A patent/FR4415M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH441345A (en) | 1967-08-15 |
| GB1048868A (en) | 1966-11-23 |
| BE658845A (en) | 1965-07-26 |
| NL123600C (en) | |
| CH443321A (en) | 1967-09-15 |
| ES308569A1 (en) | 1965-07-01 |
| GB1048869A (en) | 1966-11-23 |
| NL6500954A (en) | 1965-07-28 |
| FR4416M (en) | 1966-09-12 |
| FR4415M (en) | 1966-09-12 |
| NL6500953A (en) | 1965-07-28 |
| AT250972B (en) | 1966-12-12 |
| AT251590B (en) | 1967-01-10 |
| BE658844A (en) | 1965-07-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IE791945L (en) | Indoles. | |
| FI810389L (en) | FRAMEWORK FOR IMMEDIATE SUBSTITUTION | |
| ES431515A1 (en) | 2-Heteroaryl-methyl)-5,9{62 -dialkyl-6,7-benzomorphans and salts thereof | |
| IE41528L (en) | Furfuryl-benzomorphane derivatives. | |
| ES308570A1 (en) | New pyridobenzothiadiazepine derivatives and process for producing same | |
| ATE59387T1 (en) | 1,3-DIOXANE-4-YLALENE ACID. | |
| ES427115A1 (en) | Novel benzoylphenylacetic acid derivatives | |
| ES449777A1 (en) | Substituted pyrimido-quinoline derivatives and pharmaceutical compositions containing them | |
| ES468486A1 (en) | 1-(3-(3,4,5-trimethoxyphenoxy)-2-hydroxypropyl)-4-aryl piperazine derivatives | |
| GB1504707A (en) | 1-aryl-2-oxo-2,4,5,6,7,7a-hexahydroindoles | |
| ES304833A1 (en) | Imidazole derivatives | |
| ES8106714A1 (en) | 1,2,4-Oxadiazine derivatives, process for their preparation and pharmaceutical compositions containing them | |
| ES421518A1 (en) | Novel benzodiazepine derivatives and preparation thereof | |
| GB1488412A (en) | Imidazo(1,2-a)quinolines | |
| GB1036419A (en) | A process for the manufacture of isoquinoline derivatives | |
| GB1282405A (en) | Piperidine spiro compounds and pharmaceutical preparations thereof | |
| GB1170194A (en) | 5-Substituted 4,5-Dihydro-1,3,4-Thiadiazole-2-Thiols, Salts thereof and their production | |
| GB1018807A (en) | Novel tetrahydro-pyridine derivatives and the manufacture thereof | |
| ES8207535A1 (en) | A procedure for the preparation of imidazodiacepine derivatives (Machine-translation by Google Translate, not legally binding) | |
| JPS5479201A (en) | Preparation of aldehydes |