GB797794A - Improvements relating to sulphonamides of benzoic acid esters - Google Patents
Improvements relating to sulphonamides of benzoic acid estersInfo
- Publication number
- GB797794A GB797794A GB184/57A GB18457A GB797794A GB 797794 A GB797794 A GB 797794A GB 184/57 A GB184/57 A GB 184/57A GB 18457 A GB18457 A GB 18457A GB 797794 A GB797794 A GB 797794A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- benzoic acid
- chloride
- ester
- 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
- 150000001558 benzoic acid derivatives Chemical class 0.000 title 1
- 150000003456 sulfonamides Chemical class 0.000 title 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- HWAQOZGATRIYQG-UHFFFAOYSA-N 4-sulfobenzoic acid Chemical compound OC(=O)C1=CC=C(S(O)(=O)=O)C=C1 HWAQOZGATRIYQG-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- UCAGLBKTLXCODC-UHFFFAOYSA-N carzenide Chemical compound NS(=O)(=O)C1=CC=C(C(O)=O)C=C1 UCAGLBKTLXCODC-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- KDNIOKSLVIGAAN-UHFFFAOYSA-N 2-sulfamoylbenzoic acid Chemical compound NS(=O)(=O)C1=CC=CC=C1C(O)=O KDNIOKSLVIGAAN-UHFFFAOYSA-N 0.000 abstract 1
- JYJUMAFOXPQPAU-UHFFFAOYSA-N 4-chlorosulfonylbenzoyl chloride Chemical compound ClC(=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JYJUMAFOXPQPAU-UHFFFAOYSA-N 0.000 abstract 1
- SOSVTEHBZNSARP-UHFFFAOYSA-N 4-sulfamoylbenzoyl chloride Chemical compound NS(=O)(=O)C1=CC=C(C(Cl)=O)C=C1 SOSVTEHBZNSARP-UHFFFAOYSA-N 0.000 abstract 1
- 239000005711 Benzoic acid Substances 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 230000029142 excretion Effects 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 125000003386 piperidinyl group Chemical group 0.000 abstract 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical group ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- 238000005809 transesterification reaction Methods 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises esters of sulphamoyl benzoic acid of the formula <FORM:0797794/IV (b)/1> wherein R and R1 are hydrogen atoms or alkyl groups, together having from 4 to 10 carbon atoms, R1 and R2 are each a hydrogen atom or an alkyl, cyclohexyl or benzyl group or together with the nitrogen atom form a morpholine or piperidine ring, and their preparation by (a) trans-esterification of a lower alkyl ester of a p-sulphamoylbenzoic acid, such as the methyl or ethyl ester, with an aminoalcohol; (b) reacting a p-sulphamoylbenzoyl chloride with an aminoalcohol; (c) reacting a salt of a p-sulphamoyl benzoic acid with an amino-alkyl halide; or (d) esterifying the dichloride of p-sulpho-benzoic acid with an amino-alcohol followed by treatment with an amine to convert the sulphonyl chloride group to the amide. Examples describe the preparation of p-N : N-di-n-propylsulphamoyl-benzoic acid b - cyclohexylaminoethyl and b -benzylaminoethyl esters; p-N : N-diethylsulphamoylbenzoic acid b - dimethylaminoethyl ester; p-N : N-dibutylsulphamoylbenzoic acid b -diethylaminoethyl ester and p-N-ethyl - N - butyl - sulphamoylbenzoic acid b -morpholinoethyl ester. The products are used therapeutically to retard the excretion of drugs. Starting materials. p - N : N - Di - n - propylsulphamoylbenzoyl chloride is made by the action of thionyl chloride on the free acid. p-Chlorosulphonylbenzoyl chloride is made by the action of phosphorus pentachloride on the potassium salt of p-sulphobenzoic acid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE797794X | 1956-01-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB797794A true GB797794A (en) | 1958-07-09 |
Family
ID=20339807
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB184/57A Expired GB797794A (en) | 1956-01-18 | 1957-01-02 | Improvements relating to sulphonamides of benzoic acid esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB797794A (en) |
-
1957
- 1957-01-02 GB GB184/57A patent/GB797794A/en not_active Expired
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