US3207758A - Certain 2-(benzenesulfonamido)-5-alkoxypyrimidines - Google Patents
Certain 2-(benzenesulfonamido)-5-alkoxypyrimidines Download PDFInfo
- Publication number
- US3207758A US3207758A US118534A US11853461A US3207758A US 3207758 A US3207758 A US 3207758A US 118534 A US118534 A US 118534A US 11853461 A US11853461 A US 11853461A US 3207758 A US3207758 A US 3207758A
- Authority
- US
- United States
- Prior art keywords
- sulfonamido
- pyrimidine
- benzene
- methylbenzene
- ethoxy
- 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 - Lifetime
Links
Classifications
-
- 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
- C07D239/69—Benzenesulfonamido-pyrimidines
Definitions
- the present invention relates to sulfonamides and more particularly to 2 benzene sulfonamido S-alkoxypyrimidines.
- sulfonamides are obtained with an intensive and long lasting blood sugar depressant activity, when 2-amino-S-aIkoXy-pyrimidines, in which the alkyl residue has a straight or branched chain and possesses 2 to 5 carbon atoms, are reacted in the presence of acid binding agents with benzene sulfochloride or with benzene sulfochlorides which are substituted in the benzene nucleus by lower alkyl and/or alkoxy residues and/or halogen atoms, or when the reaction products of the Vilsmeier reaction between alkoxyacetaldehyde acetals or between 1,2-dialkoxyethylenes, in which the alkyl residue has a straight or branched chain and possesses 2 to 5 carbon atoms, and N,N-disubstituted formamides and inorganic acid chlorides, are condensed in the presence of basic condensation agents, with benzene sulfonyl
- the 2-amino-5-alkoxy-pyrimidines employed as starting materials for the first mentioned method of execution can be prepared by the process described in the copending application Serial No. 54,836, filed September 9, 1960, and now abandoned.
- Tertiary organic bases such as pyridine or triethylamine, are the preferred suitable acid-binding agents.
- Dimethyl formamide is the preferred suitable N,N- disubstituted formamide in the sense of the second method of execution, and phosgene is the preferred suitable inorganic acid chloride.
- the condensation is carried out within a temperature range of 50-200 C., preferably in an aliphatic alcohol; alkali metal alcoholates or alkali metal hydroxides are particularly suitable as condensation agents.
- the 2 benzene-sulfonamido-5-alkoxy-pyrimidines obtained according to the process lead to a distinctly exhibited and long lasting depression of the blood sugar level upon administration to experimental animals (rabbit, dog).
- a single oral administration of 250 mg./ kg. of 2 (4 methylbenzene sulfonamido) 5 npropoxy-pyrimidine to a rabbit with normal metabolism 3,207,758 Patented Sept. 21, 1965 can achieve a 54% depression in the blood sugar level within the first 6 hours.
- the depression in the blood sugar level is still maintained to the same extent 24 hours after the start of the experiment.
- a maximum depression in the blood sugar level of 45% can be obtained in 5 hours under the same experimental conditions with 250 mg./kg. of N-(4-aminobenzenesulfonyl -N-n-butyl-urea.
- the Z-benzene-sulfonamido-5-alkoxy-pyrimidines have a superior effect compared with the Z-sulfanilamido-S- alkoxy-pyrimidines with 2 to 4 carbon atoms in the alkyl residue, as known from the copending application Serial No. 54,853, filed September 9, 1960, and now abandoned. Moreover, they are also distinguished by their lack of undesirable bacteriostatic properties.
- Example 1 14 g. (0.1 mole) of 2-amino-S-ethQXy-pyrimidine are dissolved in ml. of pyridine. 17.5 g. (0.1 mole) of benzene sulfochloride are added dropwise with stirring and on cooling by ice/common salt. The temperature is allowed to rise gradually, and it is stirred oveinight at room temperature. After heating to 100 C. bath temperature for one hour, the pyridine is distilled oil in vacuo, the residue is digested with dilute hydrochloric acid on the Water bath, and after cooling with ice, it is filtered off with suction.
- 2-(4-methyl'benzene-sul fonamido) 5 isopnopoxy-pyrimidine of M .P. 186187 C. from Z amino-Sdsopropoxypyrimidine and p-toluene sulfochloride;
- Example 2 80 g. (0.25 mole) of ethoxy-acetaldehyde diethylacetal are brought to reaction in 300 ml. of methylene chloride with 73 g. of dimethyl formamide and g. of phosgene in analogy to the directions stated by Z. Arnold and F. Srm (Coll. Czechoslovak Chem. Commun. 23 (1958), 452). After neutralization with a methanol solution of sodium methylate and evaporation of the solvent in vacuo there are obtained 82.5 g. of an oily reaction product, which is added dropwise to a suspension of 96 g.
- 2-benzenesulfonamido-5-n-propoXy-pyrimidine of MI. 181182 C. starting from n-propoXy-acetaldehyde di-npropyl-acetal, by Vilsmeier-Haak reaction with dimethyl formamide and phosgene, and by condensation of the reaction product With benzene-sulfonylguanidine.
- X is a member selected from the group consisting of hydrogen, chlorine, methyl and methoxy; and R is a member selected from the group consisting of ethyl, propyl, isopropyl and butyl.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF0031592 | 1960-07-06 | ||
DEF0031983 | 1960-08-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3207758A true US3207758A (en) | 1965-09-21 |
Family
ID=25974711
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US118534A Expired - Lifetime US3207758A (en) | 1960-07-06 | 1961-06-21 | Certain 2-(benzenesulfonamido)-5-alkoxypyrimidines |
Country Status (5)
Country | Link |
---|---|
US (1) | US3207758A (de) |
CH (2) | CH437311A (de) |
DE (2) | DE1302650C2 (de) |
FR (1) | FR2757M (de) |
GB (1) | GB913716A (de) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3293259A (en) * | 1965-08-13 | 1966-12-20 | American Home Prod | Certain 1-arylsulfonyl-1, 2, 4-triazoles |
US3331841A (en) * | 1961-02-22 | 1967-07-18 | Schering Ag | Certain derivatives of 2-amino-5-alkoxypyrimidine |
US3980781A (en) * | 1966-03-31 | 1976-09-14 | Imperial Chemical Industries Limited | Fungicidal composition and method containing 2-amino-pyrimidines |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2535635A (en) * | 1948-05-06 | 1950-12-26 | American Cyanamid Co | Substituted pyrimidines and preparation of the same |
US2563725A (en) * | 1949-05-10 | 1951-08-07 | American Cyanamid Co | Phenolsulfonamides |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3037977A (en) * | 1958-10-25 | 1962-06-05 | Basf Ag | Production of compounds of the pyrimidine series |
-
1960
- 1960-07-06 DE DE19601302650D patent/DE1302650C2/de not_active Expired
- 1960-08-26 DE DE19601445028 patent/DE1445028B1/de active Pending
-
1961
- 1961-05-23 CH CH272566A patent/CH437311A/de unknown
- 1961-05-23 CH CH598661A patent/CH431536A/de unknown
- 1961-06-21 US US118534A patent/US3207758A/en not_active Expired - Lifetime
- 1961-07-29 GB GB23622/61A patent/GB913716A/en not_active Expired
-
1962
- 1962-12-17 FR FR918862A patent/FR2757M/fr not_active Expired
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2535635A (en) * | 1948-05-06 | 1950-12-26 | American Cyanamid Co | Substituted pyrimidines and preparation of the same |
US2563725A (en) * | 1949-05-10 | 1951-08-07 | American Cyanamid Co | Phenolsulfonamides |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3331841A (en) * | 1961-02-22 | 1967-07-18 | Schering Ag | Certain derivatives of 2-amino-5-alkoxypyrimidine |
US3293259A (en) * | 1965-08-13 | 1966-12-20 | American Home Prod | Certain 1-arylsulfonyl-1, 2, 4-triazoles |
US3980781A (en) * | 1966-03-31 | 1976-09-14 | Imperial Chemical Industries Limited | Fungicidal composition and method containing 2-amino-pyrimidines |
Also Published As
Publication number | Publication date |
---|---|
CH431536A (de) | 1967-03-15 |
DE1302650C2 (de) | 1974-02-07 |
CH437311A (de) | 1967-06-15 |
GB913716A (en) | 1962-12-28 |
FR2757M (fr) | 1964-08-31 |
DE1445028B1 (de) | 1970-03-26 |
DE1302650B (de) | 1973-07-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3732225A (en) | Pyrazolo(3,4-d)pyrimidine derivatives | |
JPH0714925B2 (ja) | ヘテロアリールオキシアセトアミドの製法 | |
US2913454A (en) | Certain cycloalkanotriazoles, process and intermediates | |
US3300488A (en) | Nu, nu'-bis [4-halogenated-5-alkyl-3-isoxazolylsulfamoyl)-phenyl]-ureas | |
US3920653A (en) | 1-Aminouracil compounds and herbicidal compositions | |
US5693800A (en) | N-(2-amino-4,6-dichloropyrimidine-5-yl) formamide and a process for its preparation | |
US3847914A (en) | 4-amino-1,2,4-triazine-5-one,and a process for their production | |
US3207758A (en) | Certain 2-(benzenesulfonamido)-5-alkoxypyrimidines | |
US3076817A (en) | New j-amino-thiophene-z | |
KR920006782B1 (ko) | 피리미딘 유도체 | |
IL145888A (en) | Process for the preparation of converted pyrimidines | |
US3180866A (en) | Substituted sulfapyrimidine derivatives | |
US4175184A (en) | Manufacture of 2,1,3-thiadiazin-4-one-2,2-dioxide derivatives | |
US2698326A (en) | S-aminomethylpyrimtoines | |
US3328395A (en) | 6-halo-2-amino substituted-4-sulfanilamido-pyrimidine compounds | |
US3840551A (en) | 4-substituted-alkyl-1,3,4-thiadiazolon-(5)-yl-(2)-urea compounds | |
US5446154A (en) | Process for the preparation of aminotriazine derivatives | |
US3311614A (en) | Heterocyclic amides and methods for their production | |
US3037977A (en) | Production of compounds of the pyrimidine series | |
US4738960A (en) | 1,3,4-Thiadiazole derivatives and pharmaceutical preparations useful as inhibitors for histamine-H2 receptors | |
KR860001568B1 (ko) | 선택적 설폰화 방법에 의한 페닐렌디아민 유도체의 제조 방법 | |
US2980678A (en) | Pyrimidines | |
US5288867A (en) | Process for the preparation of 2-hydroxy-4,6-diaryl-1,3,5-triazines | |
US4581175A (en) | N'-acylhydrazine-N-thiocarboxylic acid O-carbamoylmethyl esters | |
US3091610A (en) | Sulfa compounds and processes |