GB946864A - Method for the production of 3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxides - Google Patents
Method for the production of 3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxidesInfo
- Publication number
- GB946864A GB946864A GB1616960A GB1616960A GB946864A GB 946864 A GB946864 A GB 946864A GB 1616960 A GB1616960 A GB 1616960A GB 1616960 A GB1616960 A GB 1616960A GB 946864 A GB946864 A GB 946864A
- Authority
- GB
- United Kingdom
- Prior art keywords
- treating
- aliphatic hydrocarbon
- group
- formula
- alkyl
- 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
- OKXYPUDKVYVJDI-UHFFFAOYSA-N 3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical class C1=CC=C2S(=O)(=O)NCNC2=C1 OKXYPUDKVYVJDI-UHFFFAOYSA-N 0.000 title 1
- -1 monocyclic aliphatic hydrocarbon Chemical class 0.000 abstract 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical group 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002950 monocyclic group Chemical group 0.000 abstract 2
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- SUHSQRWBSWMOJY-UHFFFAOYSA-N 2,2-dimethoxyethylcyclopentane Chemical compound COC(CC1CCCC1)OC SUHSQRWBSWMOJY-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- LEEWRICIBNMZRW-UHFFFAOYSA-M [Br-].[Mg+]CC1CCCC1 Chemical compound [Br-].[Mg+]CC1CCCC1 LEEWRICIBNMZRW-UHFFFAOYSA-M 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- DTMHTVJOHYTUHE-UHFFFAOYSA-N thiocyanogen Chemical compound N#CSSC#N DTMHTVJOHYTUHE-UHFFFAOYSA-N 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 1
Classifications
-
- 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
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
- C07D285/18—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines
- C07D285/20—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems
- C07D285/22—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D285/24—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom
- C07D285/26—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom substituted in position 6 or 7 by sulfamoyl or substituted sulfamoyl radicals
- C07D285/28—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom substituted in position 6 or 7 by sulfamoyl or substituted sulfamoyl radicals with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached in position 3
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
-
- 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
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
- C07D285/18—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines
- C07D285/20—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems
- C07D285/22—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D285/24—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom
- C07D285/26—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom substituted in position 6 or 7 by sulfamoyl or substituted sulfamoyl radicals
- C07D285/30—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom substituted in position 6 or 7 by sulfamoyl or substituted sulfamoyl radicals with hydrocarbon radicals, substituted by hetero atoms, attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
3:4 - Dihydro - 1:2:4 - benzothiadiazine - 1:1 - dioxides of the formula: <FORM:0946864/C2/1> in which R1 is halogen, e.g. Cl or Br, or CF3, R2 is hydrogen or a C1-6 aliphatic hydrocarbon radical, a C3-6 monocyclic aliphatic hydrocarbon, e.g. cycloalkyl or cycloalkenyl, radical, an alkyl group substituted by a C3-6 monocyclic aliphatic hydrocarbon radical or a phenyl, phenylalkyl or phenylalkyl radical, all of which radicals may optionally bear halogen, nitro or esterified or etherified hydroxy or mercapto substituents, R3 and R4 are hydrogen or alkyl, phenyl, phenylalkyl or C3-6 monocyclic aliphatic hydrocarbon groups or alkyl groups substituted by a C3-6 monocyclic aliphatic hydrocarbon group, or R3 and R4 form with the N-atom of the sulphamoyl group a heterocyclic ring such as piperidine, pyrrolidine or morpholine and R5 is a hydrogen atom or a C1-6 alkyl or alkenyl group, are prepared by treating a disulphide of the formula: <FORM:0946864/C2/2> wherein X is an amino group and Y is a substituted or unsubstituted sulphamyl group or X and Y together with the two carbon atoms of the benzene ring form a dihydrothiadiazine ring (optionally bearing substituents R2 and R5), with oxidising and sulphonyl halide forming agents, e.g. (a) with hydrogen peroxide to give a sulphinic acid which is then treated with an aqueous solution of a halogen, (b) with an excess of hydrogen peroxide to give a suplhonic acid which is halogenated with an inorganic acid halide, or (c) in one step by treating the compound of formula II with chlorine; treating the 2 - sulphamoyl-aniline - 4 - sulphonyl halide if formed i.e. in the case where X is amino and Y is sulphamoyl with an aldehyde R2CHO to effect cyclization and condensing the resulting 3,4 - dihydrobenzo -thiadiazine - 7 - sulphonyl halide with ammonia or an amine R3-NH-R4. Bis - (6 - R1 - 3,4 - dihydro - 1,2,4 - benzothiadiazine - 1,1 - dioxide-7) - disulphides corresponding to the formula II wherein X and Y form a dihydrothiadiazine ring, are prepared by treating a 5 - R1 - 2 - sulphamyl - aniline with thiocyanogen in acetic acid, treating the resulting 4-thiocyanate with ammonia to give a bis-(2-R1-4-amino-5-sulphamyl - phenyl) - disulphide and condensing with an aldehyde R2CHO. Cyclopentyl - acetaldehyde - dimethylacetal is made by reaction of methylorthoformate with cyclopentylmethyl magnesium bromide. Specifications 847,064, 861,367 and 863,474 are referred to.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1616960A GB946864A (en) | 1960-05-06 | 1960-05-06 | Method for the production of 3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxides |
| CH506161A CH393341A (en) | 1960-05-06 | 1961-05-01 | Process for the preparation of substituted 3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxydes |
| DK184864A DK104349C (en) | 1960-05-06 | 1961-05-05 | Process for the preparation of substituted 3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide derivatives. |
| DK185961A DK105274C (en) | 1960-05-06 | 1961-05-05 | Process for the preparation of substituted 3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide derivatives. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1616960A GB946864A (en) | 1960-05-06 | 1960-05-06 | Method for the production of 3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxides |
| DEL0038926 | 1961-05-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB946864A true GB946864A (en) | 1964-01-15 |
Family
ID=25985420
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1616960A Expired GB946864A (en) | 1960-05-06 | 1960-05-06 | Method for the production of 3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB946864A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999042456A3 (en) * | 1998-02-18 | 1999-10-07 | Neurosearch As | Novel compounds and their use as positive ampa receptor modulators |
| US6943159B1 (en) | 1998-02-18 | 2005-09-13 | Neurosearch A/S | Compounds and their use as positive AMPA receptor modulators |
-
1960
- 1960-05-06 GB GB1616960A patent/GB946864A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999042456A3 (en) * | 1998-02-18 | 1999-10-07 | Neurosearch As | Novel compounds and their use as positive ampa receptor modulators |
| US6943159B1 (en) | 1998-02-18 | 2005-09-13 | Neurosearch A/S | Compounds and their use as positive AMPA receptor modulators |
| US7235548B2 (en) | 1998-02-18 | 2007-06-26 | Neurosearch A/S | Compounds and their use as positive AMPA receptor modulators |
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