GB687760A - Improvements relating to the preparation of heterocyclic sulphonamides - Google Patents
Improvements relating to the preparation of heterocyclic sulphonamidesInfo
- Publication number
- GB687760A GB687760A GB6980/51A GB698051A GB687760A GB 687760 A GB687760 A GB 687760A GB 6980/51 A GB6980/51 A GB 6980/51A GB 698051 A GB698051 A GB 698051A GB 687760 A GB687760 A GB 687760A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphonamide
- thiadiazole
- acetylamino
- dimethyl
- triazole
- 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
- -1 heterocyclic sulphonamides Chemical class 0.000 title abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- YOGFGFKRNRQDMF-UHFFFAOYSA-N n-(1,3,4-thiadiazol-2-yl)acetamide Chemical compound CC(=O)NC1=NN=CS1 YOGFGFKRNRQDMF-UHFFFAOYSA-N 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- SDYMYAFSQACTQP-UHFFFAOYSA-N 1,3-benzothiazole-2-sulfonamide Chemical compound C1=CC=C2SC(S(=O)(=O)N)=NC2=C1 SDYMYAFSQACTQP-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- BZKPWHYZMXOIDC-UHFFFAOYSA-N acetazolamide Chemical compound CC(=O)NC1=NN=C(S(N)(=O)=O)S1 BZKPWHYZMXOIDC-UHFFFAOYSA-N 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- 229910052799 carbon Chemical group 0.000 abstract 2
- 238000005660 chlorination reaction Methods 0.000 abstract 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 2
- OVOBOOXCCBSRSX-UHFFFAOYSA-N 1,3,4-thiadiazole-2,5-disulfonamide Chemical compound NS(=O)(=O)C1=NN=C(S(N)(=O)=O)S1 OVOBOOXCCBSRSX-UHFFFAOYSA-N 0.000 abstract 1
- BKQJQGVEAVLYDW-UHFFFAOYSA-N 1-methylimidazole-2-sulfonamide Chemical compound CN1C=CN=C1S(N)(=O)=O BKQJQGVEAVLYDW-UHFFFAOYSA-N 0.000 abstract 1
- ZSWKHJHMCUCZMD-UHFFFAOYSA-N 1-methyltetrazole-5-sulfonamide Chemical compound CN1N=NN=C1S(N)(=O)=O ZSWKHJHMCUCZMD-UHFFFAOYSA-N 0.000 abstract 1
- YIFYAJKPQNLXKX-UHFFFAOYSA-N 1-phenylimidazole-2-sulfonamide Chemical compound NS(=O)(=O)C1=NC=CN1C1=CC=CC=C1 YIFYAJKPQNLXKX-UHFFFAOYSA-N 0.000 abstract 1
- VSAQUMIDDSODLX-UHFFFAOYSA-N 1-phenyltetrazole-5-sulfonamide Chemical compound NS(=O)(=O)C1=NN=NN1C1=CC=CC=C1 VSAQUMIDDSODLX-UHFFFAOYSA-N 0.000 abstract 1
- WXJWETDFIWKUHH-UHFFFAOYSA-N 1h-1,2,4-triazole-5-sulfonamide Chemical compound NS(=O)(=O)C=1N=CNN=1 WXJWETDFIWKUHH-UHFFFAOYSA-N 0.000 abstract 1
- XRGHQBXKSHAQRB-UHFFFAOYSA-N 1h-benzimidazole-2-sulfonamide Chemical compound C1=CC=C2NC(S(=O)(=O)N)=NC2=C1 XRGHQBXKSHAQRB-UHFFFAOYSA-N 0.000 abstract 1
- PMTLRCDQMKXMRZ-UHFFFAOYSA-N 1h-imidazole-2-sulfonamide Chemical compound NS(=O)(=O)C1=NC=CN1 PMTLRCDQMKXMRZ-UHFFFAOYSA-N 0.000 abstract 1
- JRDPRXWPTQTRLO-UHFFFAOYSA-N 4,6-dimethylpyrimidine-2-sulfonamide Chemical compound CC1=CC(C)=NC(S(N)(=O)=O)=N1 JRDPRXWPTQTRLO-UHFFFAOYSA-N 0.000 abstract 1
- SJDMOSPRBBRSNN-UHFFFAOYSA-N 4-phenyl-1,2,4-triazole-3,5-disulfonamide Chemical compound NS(=O)(=O)C1=NN=C(S(N)(=O)=O)N1C1=CC=CC=C1 SJDMOSPRBBRSNN-UHFFFAOYSA-N 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- VGMVBPQOACUDRU-UHFFFAOYSA-N 5-amino-1,3,4-thiadiazole-2-sulfonamide Chemical compound NC1=NN=C(S(N)(=O)=O)S1 VGMVBPQOACUDRU-UHFFFAOYSA-N 0.000 abstract 1
- TZHICOZZSDYQDD-UHFFFAOYSA-N 5-chloropyrimidine-2-sulfonamide Chemical compound NS(=O)(=O)C1=NC=C(Cl)C=N1 TZHICOZZSDYQDD-UHFFFAOYSA-N 0.000 abstract 1
- IPZKOCFYORORNC-UHFFFAOYSA-N 5-oxo-4-phenyl-1h-1,2,4-triazole-3-sulfonamide Chemical compound NS(=O)(=O)C1=NN=C(O)N1C1=CC=CC=C1 IPZKOCFYORORNC-UHFFFAOYSA-N 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- AYSYSOQSKKDJJY-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]pyridine Chemical compound C1=CC=CN2C=NN=C21 AYSYSOQSKKDJJY-UHFFFAOYSA-N 0.000 abstract 1
- ACCQHQNXQXBKLK-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]pyridine-3-sulfonamide Chemical compound C1=CC=CN2C(S(=O)(=O)N)=NN=C21 ACCQHQNXQXBKLK-UHFFFAOYSA-N 0.000 abstract 1
- PFRUBEOIWWEFOL-UHFFFAOYSA-N [N].[S] Chemical group [N].[S] PFRUBEOIWWEFOL-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000011260 aqueous acid Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 229940125782 compound 2 Drugs 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- XTIHOBZPEKJCRA-UHFFFAOYSA-N pyrazine-2-sulfonamide Chemical compound NS(=O)(=O)C1=CN=CC=N1 XTIHOBZPEKJCRA-UHFFFAOYSA-N 0.000 abstract 1
- WJJBIYLGJUVNJX-UHFFFAOYSA-N pyrimidine-2-sulfonamide Chemical compound NS(=O)(=O)C1=NC=CC=N1 WJJBIYLGJUVNJX-UHFFFAOYSA-N 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D233/84—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 2
- C07D235/28—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D241/18—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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 to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 2
- C07D277/70—Sulfur atoms
- C07D277/76—Sulfur atoms attached to a second hetero atom
- C07D277/80—Sulfur atoms attached to a second hetero atom to a nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US687760XA | 1950-04-04 | 1950-04-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB687760A true GB687760A (en) | 1953-02-18 |
Family
ID=22084635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6980/51A Expired GB687760A (en) | 1950-04-04 | 1951-03-22 | Improvements relating to the preparation of heterocyclic sulphonamides |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE502319A (enrdf_load_stackoverflow) |
| DE (1) | DE915809C (enrdf_load_stackoverflow) |
| FR (2) | FR1034958A (enrdf_load_stackoverflow) |
| GB (1) | GB687760A (enrdf_load_stackoverflow) |
| NL (1) | NL77246C (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2597478A1 (fr) * | 1986-04-21 | 1987-10-23 | Esteve Labor Dr | Benzimidazoles et imidazopyridines sulfonamides, leur preparation et leur application en tant que medicaments. |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2744907A (en) * | 1954-01-27 | 1956-05-08 | American Cyanamid Co | Production of heterocyclic sulfonyl chlorides |
| US2868800A (en) * | 1954-10-13 | 1959-01-13 | Upjohn Co | 6-ethoxybenzothiazole-2-sulfonamide |
| DE1024973B (de) * | 1955-07-15 | 1958-02-27 | Schering Ag | Verfahren zur Herstellung von 2-Acylamino-1, 3, 4-thiodiazol-5-sulfonacylamiden |
| DE1103341B (de) * | 1957-04-04 | 1961-03-30 | Omikron Gagliardi Societa Di F | Verfahren zur Herstellung von heterocyclischen Sulfohalogeniden |
| IT1176613B (it) * | 1984-08-14 | 1987-08-18 | Ravizza Spa | Derivati piperazinici farmacologicamente attivi e processo per la loro preparazione |
-
0
- NL NL77246D patent/NL77246C/xx active
- BE BE502319D patent/BE502319A/xx unknown
-
1951
- 1951-03-22 GB GB6980/51A patent/GB687760A/en not_active Expired
- 1951-03-30 DE DEA13119A patent/DE915809C/de not_active Expired
- 1951-04-02 FR FR1034958D patent/FR1034958A/fr not_active Expired
-
1955
- 1955-06-16 FR FR55543A patent/FR72707E/fr not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2597478A1 (fr) * | 1986-04-21 | 1987-10-23 | Esteve Labor Dr | Benzimidazoles et imidazopyridines sulfonamides, leur preparation et leur application en tant que medicaments. |
| EP0246126A1 (fr) * | 1986-04-21 | 1987-11-19 | Laboratorios Del Dr. Esteve, S.A. | Benzimidazoles et imidazopyridines sulfonamides, leur préparation et leur application en tant que médicaments |
| US4933338A (en) * | 1986-04-21 | 1990-06-12 | Laboratorios Del Dr. Esteve, S.A. | Benzimidazolesulfonamides and their application as drugs |
Also Published As
| Publication number | Publication date |
|---|---|
| DE915809C (de) | 1954-07-29 |
| FR72707E (fr) | 1960-04-28 |
| BE502319A (enrdf_load_stackoverflow) | |
| FR1034958A (fr) | 1953-08-10 |
| NL77246C (enrdf_load_stackoverflow) |
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