You’re using a public version of DrugPatentWatch with 5 free searches available | Register to unlock more free searches. CREATE FREE ACCOUNT

Last Updated: March 28, 2024

Claims for Patent: 3,669,966


✉ Email this page to a colleague

« Back to Dashboard


Summary for Patent: 3,669,966
Title: PYRAZINE DERIVATIVES AND PROCESS FOR THEIR PREPARATION
Abstract:Pyrazine derivatives wherein a pyrazine ring is introduced into benzenesulphonyl-urea compounds, typified by the compound are disclosed. These compounds have hypoglycemic properties and are useful in the treatment of diabetic conditions.
Inventor(s): Ambrogi; Vittorio (Bresso, IT), Logemann; Willy (Milan, IT)
Assignee: Carlo Erba S.p.A. (Milan, IT)
Application Number:05/022,389
Patent Claims: 1. A compound of the formula

wherein R.sub.1, R.sub.2 and R.sub.3 are independently selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy and amino, and R.sub.4 is selected from the group consisting of lower alkyl and cycloaliphatic of five to eight carbon atoms.

2. The compound as claimed in claim 1, wherein said cycloaliphatic radical is a cycloalkyl radical of five to six carbon atoms.

3. The compound as claimed in claim 1 wherein said compound is N-{ 4-[.beta.-(pyrazine-2-carboxy-amido)-ethyl]-benzene-sulphonyl} -N'-cyclo-hexyl-urea.

4. The compound as claimed in claim 1 wherein said compound is N-{4-[.beta.-(6-methoxy-pyrazine-2-carboxy-amido)-ethyl]-benzene-sulphonyl } -N'-cyclo-hexyl-urea.

5. The compound as claimed in claim 1 wherein said compound is N-{4-[.beta.-(6-chloro-pyrazine-2-carboxy-amido)-ethyl]-benzene-sulphonyl} -N'-cyclo-hexyl-urea.

6. The compound as claimed in claim 1 wherein said compound is N-{ 4-[.beta.-(5-methyl-pyrazine-2-carboxy-amido)-ethyl]-benzene-sulphonyl} -N'-cyclo-hexyl-urea.

7. The compound as claimed in claim 1 wherein said compound is N-{ 4-[.beta.-(2,3-dimethyl-pyrazine-5-carboxy-amido)-ethyl]-benzene-sulphonyl } N-'-cyclo-hexyl-urea.

8. The compound as claimed in claim 1 wherein said compound is N-{ 4-[.beta.-(3-chloro-pyrazine-2-carboxy-amido)-ethyl]-benzene-sulphony} -N'-cyclo-hexyl-urea.

9. The compound as claimed in claim 1 wherein said compound is N-{ 4-[.beta. -(2-chloro-5,6-dimethyl-pyrazine-3-carboxy-amido)-ethyl]-benzene -sulphonyl} -N'-cyclo-hexyl-urea.

10. The compound as claimed in claim 1 wherein said compound is N-{ 4-[.beta.-(3-methoxy-pyrazine-2-carboxy-amido)-ethyl]-benzene-sulphonyl} -N'-cyclo-hexyl-urea.

11. The compound as claimed in claim 1 wherein said compound is N-{ 4-[.beta.-(6-methyl-pyrazine-2-carboxy-amido)-ethyl]-benzene-sulphonyl} -N'-cyclo-hexyl-urea.

12. The compound as claimed in claim 1 wherein said compound is N-{ 4-[.beta.-(5-methoxy-pyrazine-2-carboxy-amido)-ethyl]-benzene-sulphonyl} -N'-cyclo-hexyl-urea.

13. Process for the preparation of a compound of the formula

wherein R.sub.1, R.sub.2 and R.sub.3 are independently selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, hydroxy, amino, acetylamino and phenyl, wherein the lower alkyl, lower alkoxy and phenyl radicals may be substituted by at least one member selected from the group consisting of halogen, lower alkyl, lower alkoxy, R.sub.4 is selected from the group consisting of lower alkyl, lower alkenyl and cycloaliphatic of five to eight carbon atoms, wherein the cycloaliphatic radical may be substituted by at least one member selected from the group consisting of lower alkyl and lower alkoxy, said process comprising reacting at a temperature of 0.degree. to 200 .degree. C. a first compound of the formula

wherein R.sub.5 is an isocyanate or amino group or a urethane or urea residue with a second compound of the formula R.sub.4 Y wherein Y is an amine or an isocyanate radical.

14. The process as claimed in claim 13 wherein R.sub.5 is selected from the group consisting of

15. Process for the preparation of a compound of the formula

wherein R.sub.1, R.sub.2 and R.sub.3 are independently selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, hydroxy, amino, acetylamino and phenyl, wherein the lower alkyl, lower alkoxy and phenyl radicals may be substituted by at least one member selected from the group consisting of halogen, lower alkyl, lower alkoxy, R.sub.4 is selected from the group consisting of lower alkyl, lower alkenyl and cycloaliphatic of five to eight carbon atoms, wherein the cycloaliphatic radical may be substituted by at least one member selected from the group consisting of lower alkyl and lower alkoxy, said process comprising reacting at temperature of 0.degree. to 160 .degree. C. a first compound of the formula

wherein X is a carboxy group, an acid halide or a mixed anhydride, with a compound of the formula

Make Better Decisions: Try a trial or see plans & pricing

Drugs may be covered by multiple patents or regulatory protections. All trademarks and applicant names are the property of their respective owners or licensors. Although great care is taken in the proper and correct provision of this service, thinkBiotech LLC does not accept any responsibility for possible consequences of errors or omissions in the provided data. The data presented herein is for information purposes only. There is no warranty that the data contained herein is error free. thinkBiotech performs no independent verification of facts as provided by public sources nor are attempts made to provide legal or investing advice. Any reliance on data provided herein is done solely at the discretion of the user. Users of this service are advised to seek professional advice and independent confirmation before considering acting on any of the provided information. thinkBiotech LLC reserves the right to amend, extend or withdraw any part or all of the offered service without notice.