GB861367A - 3:4-dihydro-1:2:4-benzothiadiazine-1:1-dioxides - Google Patents
3:4-dihydro-1:2:4-benzothiadiazine-1:1-dioxidesInfo
- Publication number
- GB861367A GB861367A GB7209/59A GB720959A GB861367A GB 861367 A GB861367 A GB 861367A GB 7209/59 A GB7209/59 A GB 7209/59A GB 720959 A GB720959 A GB 720959A GB 861367 A GB861367 A GB 861367A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- benzothiadiazine
- carbon atoms
- hydrogen
- dihydro
- 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
-
- 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
-
- 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
-
- 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
-
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D417/06—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 carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises 3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxides of the formula <FORM:0861367/IV (b)/1> and N-acyl derivatives and salts of these compounds, in which R1, R3, R5 and R6 are eac hydrogen or alkyl, R2 is hydrogen, an aliphatic hydrocarbon radical of 1-8 carbon atoms, a cycloalkyl, cycloalkenyl, phenyl or phenylalkyl radical or a monocyclic heterocyclic or heterocyclic-alkyl radical containing one oxygen, nitrogen or sulphur atom in the ring, e.g. furan, pyridine or thiophene, all these radicals being optionally substituted by halogen atoms, free, esterified or etherified hydroxyl or mercapto groups, nitro, acylamino, mono-alkyl-, di-alkyl-or N : N-alkylene-amino groups wherein the alkylene group has 4 or 5 carbon atoms and may be interrupted by a hetero-atom, carboxyl groups or alkyl groups of 1-5 carbon atoms, R4 is a halogen atom or an alkoxy, alkyl or haloalkyl group of 1-5 carbon atoms and when R2, R3, R5 and R6 are hydrogen and R4\t is chlorine, R1 may be an alkyl or acyl group. The compounds are prepared either by reacting a 2-sulphamoyl aniline of the formula <FORM:0861367/IV (b)/2> p in which R11 and R31 stand for hydrogen or alkyl with an aldehyde R2CHO or a functional derivative thereof, preferably in the presence of a mineral acid, and, if desired, alkylating or acylating the product, or by hydrogenating the 3,4-positions of the corresponding benzothiadiazine 1,1-dioxides preferably by means of a di-metal hydride such as an alkali metal borohydride, and if desired alkylating or acylating the product. The compounds are used pharmaceutically as diuretics and natriuretics. Preferred products include the 3-propyl-, 3-butyl-, 3-chloromethyl-, 3-ethoxymethyl-, 3-phenoxymethyl-, 3-benzyl-, 3-b -phenethyl-, 3-cyclohexen-31-yl-, 2-methyl- and 4-methyl-6-chloro - 7 - sulphamoyl - 3,4 - dihydro - 1,2,4-benzothiadiazine - 1,1 - dioxide, 6 - trifluoromethyl - 7 - sulphamoyl - 3,4 - dihydro - 1,2,4-benzothiadiazine-1,1-dioxide and 2-methyl-6-chloro - 7 - methylsulphamoyl - 3,4 - dihydro-1,2,4 - benzothiadiazine - 1,1 - dioxide. Many other products are specified. 2-Sulphamoyl anilines of the formula given above, which are used as starting materials are made by the reacting aniline or an N-alkyl aniline, bearing a substituent R4 in the m-position with a halogenosulphonic acid, e.g. chlorosulphonic acid and treating the resulting disulphonyl chloride chloride with ammonia or an amine.ALSO:Diuretic and natriuretic preparations comprise benzothiadiazine compounds of the formula <FORM:0861367/VI/1> or salts or N-acyl derivatives thereof, wherein R1, R3, R5 and R6 are hydrogen or alkyl, R2 is hydrogen, an aliphatic hydrocarbon radical of 1-8 carbon atoms, a cycloalkyl, cycloalkenyl, phenyl or phenylalkyl radical or a monocyclic heterocyclic or heterocyclic-alkyl radical containing one oxygen, nitrogen or sulphur atom in the ring, e.g. furan, pyridine or thiophene, all these radicals being optionally substituted by halogen atoms, free, esterified or etherified hydroxyl or mercapto groups, nitro, acyl-amino, mono-alkyl-, di-alkyl- or N : N-alkylene-amino groups, wherein the alkylene group has 4 or 5 carbon atoms and may be interrupted by a hetero atom, carboxyl groups or alkyl groups of 1-5 carbon atoms, R4 is a halogen atom or an alkoxy, alkyl or haloalkyl group of 1-5 carbon atoms, and when R2, R3, R5 and R6 are hydrogen and R4 is chlorine, R1 may be an alkyl or acyl group (see Group IV (b)), in admixture or conjunction with a pharmaceutical carrier for oral or parenteral administration. The preparations may take the form of tablets, dragees, capsules, solutions, suspensions or emulsions and may contain other therapeutic substances, for example, hypotensive agents such as Rauwolfia or Veratrum alkaloids, e.g. reserpine, rescinnamine, deserpidine, germine or protoveratrine, or hydralazine or ganglionic blockers such as chlorisondamine. An example describes the preparation of tablets containing 3 - butyl - 6 - chloro - 7 - sulphamoyl - 3,4 - dihydro - 1,2,4 - benzothiadiazine - 1,1 - dioxide.
Applications Claiming Priority (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US71845258A | 1958-03-03 | 1958-03-03 | |
US72724258A | 1958-04-09 | 1958-04-09 | |
US74058258A | 1958-06-09 | 1958-06-09 | |
US75162058A | 1958-07-29 | 1958-07-29 | |
US76448258A | 1958-09-29 | 1958-09-29 | |
DEC0024177 | 1959-02-27 | ||
DEC0024178 | 1959-02-27 | ||
DEC0024176 | 1959-02-27 | ||
DEC0028408 | 1959-02-27 | ||
DEC0028409 | 1959-02-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB861367A true GB861367A (en) | 1961-02-22 |
Family
ID=27579177
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB7209/59A Expired GB861367A (en) | 1958-03-03 | 1959-03-02 | 3:4-dihydro-1:2:4-benzothiadiazine-1:1-dioxides |
Country Status (6)
Country | Link |
---|---|
CH (4) | CH371454A (en) |
DE (4) | DE1112079B (en) |
FR (2) | FR1217929A (en) |
GB (1) | GB861367A (en) |
MY (1) | MY6200051A (en) |
OA (2) | OA01178A (en) |
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3200117A (en) * | 1962-10-03 | 1965-08-10 | Hoffmann La Roche | Derivatives of 1, 2, 4-benzothiadiazine-7-sulfonamide-1, 1-dioxide |
WO1999042456A2 (en) * | 1998-02-18 | 1999-08-26 | Neurosearch A/S | Novel compounds and their use as positive ampa receptor modulators |
WO2004017964A1 (en) | 2002-08-19 | 2004-03-04 | Pfizer Products Inc. | Combination therapy for hyperproliferative diseases |
US6943159B1 (en) | 1998-02-18 | 2005-09-13 | Neurosearch A/S | Compounds and their use as positive AMPA receptor modulators |
WO2007062314A2 (en) | 2005-11-23 | 2007-05-31 | Bristol-Myers Squibb Company | Heterocyclic cetp inhibitors |
WO2008070496A2 (en) | 2006-12-01 | 2008-06-12 | Bristol-Myers Squibb Company | N- ( (3-benzyl) -2, 2- (bis-phenyl) -propan-1-amine derivatives as cetp inhibitors for the treatment of atherosclerosis and cardiovascular diseases |
US7732413B2 (en) | 2003-03-07 | 2010-06-08 | Schering Corporation | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof |
US7741289B2 (en) | 2003-03-07 | 2010-06-22 | Schering Corporation | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof |
WO2011069038A2 (en) | 2009-12-03 | 2011-06-09 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
EP2392567A1 (en) | 2005-10-21 | 2011-12-07 | Bristol-Myers Squibb Company | Benzothiazine derivatives and their use as lxr modulators |
WO2013138352A1 (en) | 2012-03-15 | 2013-09-19 | Synergy Pharmaceuticals Inc. | Formulations of guanylate cyclase c agonists and methods of use |
WO2014151200A2 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Compositions useful for the treatment of gastrointestinal disorders |
WO2014151206A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
WO2014170786A1 (en) | 2013-04-17 | 2014-10-23 | Pfizer Inc. | N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases |
EP2810951A2 (en) | 2008-06-04 | 2014-12-10 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
WO2014197720A2 (en) | 2013-06-05 | 2014-12-11 | Synergy Pharmaceuticals, Inc. | Ultra-pure agonists of guanylate cyclase c, method of making and using same |
EP2998314A1 (en) | 2007-06-04 | 2016-03-23 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
WO2016055901A1 (en) | 2014-10-08 | 2016-04-14 | Pfizer Inc. | Substituted amide compounds |
EP3241839A1 (en) | 2008-07-16 | 2017-11-08 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
WO2020150473A2 (en) | 2019-01-18 | 2020-07-23 | Dogma Therapeutics, Inc. | Pcsk9 inhibitors and methods of use thereof |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2642140C2 (en) * | 1976-09-20 | 1982-10-28 | Degussa Ag, 6000 Frankfurt | Process for the production of benzoyl cyanide |
DE8700284U1 (en) * | 1987-01-07 | 1987-04-30 | Ernst Reiner GmbH & Co KG, 7743 Furtwangen | Post date stamp |
-
1958
- 1958-12-16 FR FR781736A patent/FR1217929A/en not_active Expired
-
1959
- 1959-02-19 CH CH6978359A patent/CH371454A/en unknown
- 1959-02-19 CH CH18063A patent/CH376514A/en unknown
- 1959-02-19 CH CH18463A patent/CH387642A/en unknown
- 1959-02-19 CH CH18163A patent/CH377365A/en unknown
- 1959-02-27 DE DEC18496A patent/DE1112079B/en active Pending
- 1959-02-27 DE DE19591445005 patent/DE1445005A1/en active Pending
- 1959-02-27 DE DE19591445574 patent/DE1445574A1/en active Pending
- 1959-02-27 DE DE19591445007 patent/DE1445007A1/en active Pending
- 1959-03-02 GB GB7209/59A patent/GB861367A/en not_active Expired
- 1959-03-03 FR FR788246A patent/FR1264468A/en not_active Expired
-
1962
- 1962-12-30 MY MY51/62A patent/MY6200051A/en unknown
-
1964
- 1964-12-31 OA OA51359A patent/OA01178A/en unknown
-
1965
- 1965-06-29 OA OA52080A patent/OA03826A/en unknown
Cited By (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3200117A (en) * | 1962-10-03 | 1965-08-10 | Hoffmann La Roche | Derivatives of 1, 2, 4-benzothiadiazine-7-sulfonamide-1, 1-dioxide |
US7235548B2 (en) | 1998-02-18 | 2007-06-26 | Neurosearch A/S | Compounds and their use as positive AMPA receptor modulators |
WO1999042456A2 (en) * | 1998-02-18 | 1999-08-26 | Neurosearch A/S | Novel compounds and their use as positive ampa receptor modulators |
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 |
WO2004017964A1 (en) | 2002-08-19 | 2004-03-04 | Pfizer Products Inc. | Combination therapy for hyperproliferative diseases |
US7732413B2 (en) | 2003-03-07 | 2010-06-08 | Schering Corporation | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof |
US7741289B2 (en) | 2003-03-07 | 2010-06-22 | Schering Corporation | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof |
EP2392567A1 (en) | 2005-10-21 | 2011-12-07 | Bristol-Myers Squibb Company | Benzothiazine derivatives and their use as lxr modulators |
WO2007062314A2 (en) | 2005-11-23 | 2007-05-31 | Bristol-Myers Squibb Company | Heterocyclic cetp inhibitors |
WO2008070496A2 (en) | 2006-12-01 | 2008-06-12 | Bristol-Myers Squibb Company | N- ( (3-benzyl) -2, 2- (bis-phenyl) -propan-1-amine derivatives as cetp inhibitors for the treatment of atherosclerosis and cardiovascular diseases |
EP2998314A1 (en) | 2007-06-04 | 2016-03-23 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
EP2810951A2 (en) | 2008-06-04 | 2014-12-10 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
EP3241839A1 (en) | 2008-07-16 | 2017-11-08 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
EP2923706A1 (en) | 2009-12-03 | 2015-09-30 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia |
WO2011069038A2 (en) | 2009-12-03 | 2011-06-09 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
WO2013138352A1 (en) | 2012-03-15 | 2013-09-19 | Synergy Pharmaceuticals Inc. | Formulations of guanylate cyclase c agonists and methods of use |
EP3708179A1 (en) | 2012-03-15 | 2020-09-16 | Bausch Health Ireland Limited | Formulations of guanylate cyclase c agonists and methods of use |
EP4309673A2 (en) | 2012-03-15 | 2024-01-24 | Bausch Health Ireland Limited | Formulations of guanylate cyclase c agonists and methods of use |
WO2014151206A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
WO2014151200A2 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Compositions useful for the treatment of gastrointestinal disorders |
WO2014170786A1 (en) | 2013-04-17 | 2014-10-23 | Pfizer Inc. | N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases |
WO2014197720A2 (en) | 2013-06-05 | 2014-12-11 | Synergy Pharmaceuticals, Inc. | Ultra-pure agonists of guanylate cyclase c, method of making and using same |
WO2016055901A1 (en) | 2014-10-08 | 2016-04-14 | Pfizer Inc. | Substituted amide compounds |
WO2020150473A2 (en) | 2019-01-18 | 2020-07-23 | Dogma Therapeutics, Inc. | Pcsk9 inhibitors and methods of use thereof |
Also Published As
Publication number | Publication date |
---|---|
CH377365A (en) | 1964-05-15 |
CH376514A (en) | 1964-04-15 |
CH371454A (en) | 1963-08-31 |
DE1445006B2 (en) | 1975-05-07 |
DE1445008A1 (en) | 1968-10-24 |
OA03826A (en) | 1971-12-24 |
DE1445007A1 (en) | 1968-10-24 |
FR1217929A (en) | 1960-05-06 |
CH387642A (en) | 1965-02-15 |
MY6200051A (en) | 1962-12-31 |
OA01178A (en) | 1969-01-25 |
DE1112079B (en) | 1961-08-03 |
DE1445574A1 (en) | 1969-01-16 |
DE1445005A1 (en) | 1968-10-24 |
FR1264468A (en) | 1961-06-23 |
DE1445006A1 (en) | 1968-10-24 |
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