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GB795174A - Heterocyclic sulphonamides - Google Patents

Heterocyclic sulphonamides

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Publication number
GB795174A
GB795174AGB27101/55AGB2710155AGB795174AGB 795174 AGB795174 AGB 795174AGB 27101/55 AGB27101/55 AGB 27101/55AGB 2710155 AGB2710155 AGB 2710155AGB 795174 AGB795174 AGB 795174A
Authority
GB
United Kingdom
Prior art keywords
sulphenamide
sulphonamides
thiadiazole
heterocyclic
sulphonamide
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
Application number
GB27101/55A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Upjohn CofiledCriticalUpjohn Co
Publication of GB795174ApublicationCriticalpatent/GB795174A/en
Expiredlegal-statusCriticalCurrent

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Abstract

The invention comprises C-polyheterocyclic sulphonamides, i.e those containing 2 or more hetero atoms in the heterocycle, containing a sulphur atom in the alpha position to the sulphonamide group and/or having the heterocycle at least partly reduced; compounds of the formula R-SO2NR1R11 wherein -NR1R11 is a primary, secondary or tertiary amido group and R is a partially or wholly reduced thiazole, oxazole, imidazole, pyrimidine, pyrazine, pyridazine, oxazine, thiazine or thiadiazole radical; 6-ethoxybenzothiazole-2-sulphonamide; 4-phenyl-5-thiono-4 : 5-dihydro-1 : 3 : 4 - thiadiazole - 2 - sulphonamide; 6 - carboxamidobenzothiazole - 2 - sulphonamides and 6 - carboxamido - 4 - hydroxy - pyrimidine-2-sulphonamides containing from 1 to 8 carbon atoms in the carboxamido radical; and the preparation of C-heterocyclic sulphonamides in general by the oxidative condensation of a C-heterocyclic thiol and ammonia or a primary or secondary amine followed by oxidation of the resulting sulphenamide. In a modification of this process the sulphenamide is prepared by reacting a C-heterocyclic thiol with an N-chloramine. Preferably, the oxidative condensation is brought about with the aid of a hypohalite or a halogen in aqueous alkaline solution, with addition of a water-miscible solvent, e.g. ethanol or dioxan, if necessary, the temperature preferably being kept below 30 DEG C. and advantageously at 0 DEG to 10 DEG C. Acid oxidation or a two-stage process via the disulphide may also be used. The oxidation of the sulphenamides to the sulphonamides is advantageously achieved with aqueous potassium permanganate in a suitable solvent, although other oxidizing agents such as alkaline hydrogen peroxide and sodium peroxide, hydrogen peroxide in acetic acid, chromic acid, nitric acid or permanganic acid can also be used, at temperatures normally between 0 DEG and 50 DEG C. In examples: (1) 6-ethoxybenzothiazole-2-thiol in sodium hydroxide solution reacts with sodium hypochlorite solution and ammonium hydroxide at a low temperature to give 6-ethoxybenzothiazole-2-sulphenamide which on permanganate oxidation gives the corresponding sulphonamide; (2) 6-acetamidobenzothiazole-2-sulphenamide, the corresponding 4- and 6-propionamido-, 4- and 6-valeramido-, 4- and 6-caprylamido-, 4- and 6-benzamido- and 4-carboxy-6-benzamido-compounds, and the sulphonamides corresponding to all these sulphenamides are similarly prepared; (3) 4-phenyl-5-thiono-4 : 5-dihydro-1 : 3 : 4-thiadiazole-2-sulphenamide is prepared either as in (1) or by treating the corresponding disulphide with alcoholic ammonia and is then oxidized as in (1) to the corresponding sulphonamide; 4 : 4 : 6-trimethyl-1 : 2 : 3 : 4-tetrahydropyrimidine-2-, 4 : 5-dihydrothiazole-2-, 4-methyl - 4 : 5 - dihydrothiazole - 2 -, 5 : 5- di-methyl - 4 : 5 - dihydrothiazole - 2 -, 5 - ethyl - 5 - methyl - 4 : 5 - dihydrothiazole - 2 -, imidazoline-2- and 2 : 4-diketo-1 : 2 : 3 : 4-tetrahydropyrimidine-6-sulphonamides are similarly prepared; (4) 6-acetamido-4-acetoxypyrimidine 2-thiol (prepared from 6-amino-4-hydroxypyrimidine-2-thiol and acetic anhydride in pyridine) is reacted as in (1) to give 6-acetamido-4-hydroxypyrimidine-2-sulphenamide and this is oxidized as in (1) to the corresponding sulphonamide; the 6-propionamido-, 6-valeramido-, 6-caprylamido- and 6-benzamido-compounds are similarly obtained; (5) 5-acetamido-1 : 3 : 4-thiadiazole-2-sulphenamide and the corresponding sulphonamide, and the corresponding 5-propionamido-, 5-valeramido-, 5-caprylamido- and 5-benzamido-compounds are prepared as in (1). Reference is also made to the preparation of sulphonamides from thiols containing other heterocyclic radicals with one, two or more hetero atoms, not reduced or wholly or partly reduced, substituted or unsubstituted, which may be fused with one or more homo or heterocyclic rings. Specific reference is made to isoxazole, pteridine, purine, pyrrole, isoxazoline, pyrrolidine, tetrazole, triazole, pyridine, thiophene, furan, pyran, thiapyran, benzimidazole, naphthothiazole, benzoxazole, quinoline, and pyrido[2 : 1-c-]-s-triazole, in addition to the rings referred to above, to dithiols such as 1 : 2 : 4-thiadiazole-3 : 5- and -2 : 5-dithiols, to alkyl, aryl, aralkyl, alkoxy, carboxamido, halogen, thiono, oxo and hydroxy substituents in the heterocyclic rings and these and nitro groups in the fused-on aromatic rings, to N-alkyl-, N : N-dialkyl-, N-2-aminoethyl-, N-cycloalkyl-, N-alkyl-N-cycloalkyl-, N-2-pyridyl-, N-2-thiazolyl-, N-2-pyrimidyl-, N-phenyl-, N-methyl-N-phenyl-, N-2-thienyl-, N-thenyl-, N-2-furyl-, N-tolyl-, N-benzyl- and N-phenylethyl-sulphonamides and to sulphonamides in which the amide nitrogen forms part of a heterocycle such as piperidine, pyrrolidine, piperazine and morpholine and alkyl substituted derivatives thereof. Specification 377,730, [Group IV], is referred to.ALSO:Heterocyclic sulphenamides wherein the sulphenamide group is attached to a carbon atom of the heterocycle are used as vulcanization accelerators in the compounding and vulcanization of rubber. Specific reference is made to the use of 6-ethoxybenzothiazole-2-sulphenamide, 6-acetamidobenzothiazole-2-sulphenamide, 4-phenyl-5-thiono-4 : 5-dihydro-1 : 3 : 4-thiadiazole-2-sulphenamide and 5-acetamido-1 : 3 : 4-thiadiazole-2-sulphenamide as vulcanization accelerators.
GB27101/55A1954-10-131955-09-22Heterocyclic sulphonamidesExpiredGB795174A (en)

Applications Claiming Priority (1)

Application NumberPriority DateFiling DateTitle
US795174XA1954-10-131954-10-13

Publications (1)

Publication NumberPublication Date
GB795174Atrue GB795174A (en)1958-05-21

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ID=22151064

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Application NumberTitlePriority DateFiling Date
GB27101/55AExpiredGB795174A (en)1954-10-131955-09-22Heterocyclic sulphonamides

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GB (1)GB795174A (en)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication numberPriority datePublication dateAssigneeTitle
US3478030A (en)*1966-06-271969-11-11Abbott LabBenzamide substituted anilino aminopyrimidines
US3839303A (en)*1971-01-181974-10-01Monsanto CoInhibiting premature vulcanization with aminothiopyrimidines
JPS544379B1 (en)*1971-01-181979-03-06
US4483864A (en)*1983-02-041984-11-20University Of Iowa Research FoundationNon-classical topical treatment for glaucoma
US4975449A (en)*1983-02-041990-12-04University Of Iowa Research FoundationTopical treatment of glaucoma with 2-benzothiazolesulfonamide derivative
US5079305A (en)*1989-09-051992-01-07Monsanto CompanyRubber compositions comprising sulfenimide accelerators
US5374689A (en)*1992-06-051994-12-20Monsanto CompanyRubber compositions containing 2-pyrazine sulfenamides
WO2004017964A1 (en)2002-08-192004-03-04Pfizer Products Inc.Combination therapy for hyperproliferative diseases
US6878703B2 (en)2000-11-212005-04-12Sankyo Company, LimitedPharmaceutical composition
WO2007062314A2 (en)2005-11-232007-05-31Bristol-Myers Squibb CompanyHeterocyclic cetp inhibitors
CN100387584C (en)*2005-07-052008-05-14杭州保灵有限公司 A kind of preparation method of methazolamide
WO2008070496A2 (en)2006-12-012008-06-12Bristol-Myers Squibb CompanyN- ( (3-benzyl) -2, 2- (bis-phenyl) -propan-1-amine derivatives as cetp inhibitors for the treatment of atherosclerosis and cardiovascular diseases
WO2008089521A1 (en)2007-01-252008-07-31Verva Pharmaceuticals LtdInsulin sensitisers and methods of treatment
EP2392567A1 (en)2005-10-212011-12-07Bristol-Myers Squibb CompanyBenzothiazine derivatives and their use as lxr modulators
WO2014170786A1 (en)2013-04-172014-10-23Pfizer Inc.N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases
WO2015012205A1 (en)2013-07-232015-01-29第一三共株式会社Medicine for preventing or treating hypertension
WO2016055901A1 (en)2014-10-082016-04-14Pfizer Inc.Substituted amide compounds
WO2020150473A2 (en)2019-01-182020-07-23Dogma Therapeutics, Inc.Pcsk9 inhibitors and methods of use thereof

Cited By (20)

* Cited by examiner, † Cited by third party
Publication numberPriority datePublication dateAssigneeTitle
US3478030A (en)*1966-06-271969-11-11Abbott LabBenzamide substituted anilino aminopyrimidines
US3839303A (en)*1971-01-181974-10-01Monsanto CoInhibiting premature vulcanization with aminothiopyrimidines
JPS544379B1 (en)*1971-01-181979-03-06
US4483864A (en)*1983-02-041984-11-20University Of Iowa Research FoundationNon-classical topical treatment for glaucoma
US4636515A (en)*1983-02-041987-01-13University Of Iowa Research FoundationNon-classical topical treatment for glaucoma
US4975449A (en)*1983-02-041990-12-04University Of Iowa Research FoundationTopical treatment of glaucoma with 2-benzothiazolesulfonamide derivative
US5079305A (en)*1989-09-051992-01-07Monsanto CompanyRubber compositions comprising sulfenimide accelerators
US5374689A (en)*1992-06-051994-12-20Monsanto CompanyRubber compositions containing 2-pyrazine sulfenamides
US6878703B2 (en)2000-11-212005-04-12Sankyo Company, LimitedPharmaceutical composition
WO2004017964A1 (en)2002-08-192004-03-04Pfizer Products Inc.Combination therapy for hyperproliferative diseases
CN100387584C (en)*2005-07-052008-05-14杭州保灵有限公司 A kind of preparation method of methazolamide
EP2392567A1 (en)2005-10-212011-12-07Bristol-Myers Squibb CompanyBenzothiazine derivatives and their use as lxr modulators
WO2007062314A2 (en)2005-11-232007-05-31Bristol-Myers Squibb CompanyHeterocyclic cetp inhibitors
WO2008070496A2 (en)2006-12-012008-06-12Bristol-Myers Squibb CompanyN- ( (3-benzyl) -2, 2- (bis-phenyl) -propan-1-amine derivatives as cetp inhibitors for the treatment of atherosclerosis and cardiovascular diseases
WO2008089521A1 (en)2007-01-252008-07-31Verva Pharmaceuticals LtdInsulin sensitisers and methods of treatment
WO2014170786A1 (en)2013-04-172014-10-23Pfizer Inc.N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases
WO2015012205A1 (en)2013-07-232015-01-29第一三共株式会社Medicine for preventing or treating hypertension
WO2016055901A1 (en)2014-10-082016-04-14Pfizer Inc.Substituted amide compounds
WO2020150473A2 (en)2019-01-182020-07-23Dogma Therapeutics, Inc.Pcsk9 inhibitors and methods of use thereof
EP4470609A2 (en)2019-01-182024-12-04Astrazeneca ABPcsk9 inhibitors and methods of use thereof

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