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Details for Patent: 5,539,102

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Details for Patent: 5,539,102

Title: Production method for sulfamide
Abstract:The method for producing a sulfamide according to the present invention includes the step of reacting an alcohol and an oxycarbonylsulfamide compound in the presence of a trivalent phosphorus compound and an azodicarboxylic acid derivative. In one embodiment, the sulfamide is represented by Formula I, the alcohol is represented by Formula II, and the oxycarbonylsulfamide compound is represented by Formula III: wherein R.sup.1 and R.sup.2 are independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, aryl, a heterocyclic group, and alkyl substituted with the heterocyclic group, respectively, said heterocyclic group being selected from the group consisting of pyranosyl, furanosyl, piperidinyl, pyrrolidinyl, an azetidinone ring, a cephem ring, a penem ring, and a carbapenem ring; R.sup.3 is selected from the group consisting of alkyl, alkenyl, alkynyl, aralkyl, a heterocyclic group, alkyl substituted with the heterocyclic group, and pyrrolidinylmethyl, said heterocyclic group being selected from the group consisting of pyranosyl, furanosyl, piperidinyl, pyrrolidinyl, an azetidinone ring, a cephem ring, a penem ring, and a carbapenem ring; wherein R.sup.3 is defined as above; wherein R.sup.1 and R.sup.2 are defined as above; and R.sup.4 is a carboxy protecting group.
Inventor(s): Sendo; Yuji (Itami, JP), Kii; Makoto (Amagasaki, JP), Nishitani; Yasuhiro (Izumi, JP), Irie; Tadashi (Suita, JP), Nishino; Yutaka (Neyagawa, JP)
Assignee: Shionogi Seiyaku Kabushiki Kaisha (Osaka, JP)
Filing Date:Feb 18, 1993
Application Number:08/019,105
Claims:1. A method for producing a sulfamide, comprising the step of reacting an alcohol and an oxycarbonylsulfamide compound in the presence of a trivalent phosphorus compound and an azodicarboxylic acid derivative,

wherein the sulfamide is represented by formula I, the alcohol is represented by Formula II, the oxycarbonylsulfamide compound is represented by Formula III, and the trivalent phosphorus compound is trialkylphosphine, triarylphosphine, or phosphite:

wherein R.sup.1 and R.sup.2 are independently selected from the group consisting of hydrogen, alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 9 carbon atoms, alkenyl, alkynyl, aralkyl having 7 to 14 carbon atoms, aryl having 10 or less carbon atoms, a heterocyclic group, and alkyl substituted with the heterocyclic group, respectively, said heterocyclic group being selected from the group consisting of pyranosyl, furanosyl, piperidinyl, pyrrolidinyl, a cephem ring, a penem ring, and a carbapenem ring; R.sup.3 is selected from the group consisting of alkyl having 1 to 6 carbon atoms, aralkyl having 7 to 14 carbon atoms, alkyl substituted with a heterocyclic group, and pyrrolidinylmethyl, said heterocyclic group being selected from the group consisting of pyranosyl, furanosyl, piperidinyl, pyrrolidinyl, thienyl, a cephem ring, a penem ring, and a carbapenem ring;

wherein R.sup.3 is defined as above;

wherein R.sup.1 and R.sup.2 are defined as above; and R.sup.4 is a carboxy protecting group.

2. A method according to claim 1 further comprising the step of removing --COOR.sup.4.

3. A method for producing a sulfamide comprising the step of reacting an alcohol and an oxycarbonylsulfamide compound in the presence of a trivalent phosphorus compound and an azodicarboxylic acid derivative, wherein the sulfamide is represented by Formula IV, the alcohol is represented by Formula II, the oxycarbonylsulfamide compound is represented by Formula III, and the trivalent phosphorus compound is trialkylphosphine, triarylphosphine, or phosphite:

wherein R.sup.1 and R.sup.2 are independently selected from the group consisting of hydrogen, alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 9 carbon atoms, alkenyl, alkynyl, aralkyl having 7 to 14 carbon atoms, aryl having 10 or less carbon atoms, heterocyclic group, and alkyl substituted with a heterocyclic group, respectively, said heterocyclic group being selected from the group consisting of pyranosyl, furanosyl, piperidinyl, pyrrolidinyl, a cephem ring, a penem ring, and a carbapenem ring; R.sup.3 is selected from the group consisting of alkyl having 1 to 6 carbon atoms, aralkyl having 7 to 14 carbon atoms, alkyl substituted with a heterocyclic group, and pyrrolidinylmethyl, said heterocyclic group being selected from the group consisting of pyranosyl, furanosyl, piperidinyl, pyrrolidinyl, thienyl, a cephem ring, a penem ring, and a carbapenem ring; and R.sup.4 is a carboxy protecting group;

wherein R.sup.3 is defined as above;

wherein R.sup.1, R.sup.2 and R.sup.4 are defined as above.

4. The method according to claim 3,

wherein R.sup.1 and R.sup.2 are independently selected from the group consisting of hydrogen, phenyl, and alkyl substituted with a heterocyclic group, respectively, said heterocyclic group being selected from the group consisting of pyranosyl, furanosyl, piperidinyl, pyrrolidinyl, a cephem ring, a penem ring, and a carbapenem ring; R.sup.3 is selected from the group consisting of t-butyl, phenylmethyl, aralkyl having 7 to 14 carbon atoms, alkyl substituted with a heterocyclic group, and pyrrolidinylmethyl, said heterocyclic group being selected from the group consisting of pyranosyl, furanosyl, piperidinyl, pyrrolidinyl, thienyl, a cephem ring, a penem ring, and a carbapenem ring; and R.sup.4 is a carboxy protecting group.

5. The method according to claim 1, wherein the alcohol is a primary alcohol.

6. The method according to claim 3, wherein the alcohol is a primary alcohol.

7. The method according to claim 4, wherein the alcohol is a primary alcohol.

8. The method according to claim 1, wherein the trivalent phosphorous compound is triethylphosphine, tributylphosphine, triphenylphoshine, tritolylphosphine, methyl phosphite, ethyl phosphite or phenyl phosphite.

9. The method according to claim 3, wherein the trivalent phosphorous compound is triethylphosphine, tributylphosphine, triphenylphoshine, tritolylphosphine, methyl phosphite, ethyl phosphite or phenyl phosphite.

10. The method according to claim 4, wherein the trivalent phosphorous compound is triethylphosphine, tributylphosphine, triphenylphoshine, tritolylphosphine, methyl phosphite, ethyl phosphite or phenyl phosphite.

11. The method according to claim 1, wherein the azodicarboxylic acid derivative is alkyl azodicarboxylate, azodicarboxamide, bisdialkylamide of azodicarboxylic acid or 1,1'-(azodicarbonyl)dialkyleneamine.

12. The method according to claim 3, wherein the azodicarboxylic acid derivative is alkyl azodicarboxylate, azodicarboxamide, bisdialkylamide of azodicarboxylic acid or 1,1'-(azodicarbonyl)dialkyleneamine.

13. The method according to claim 4, wherein the azodicarboxylic acid derivative is alkyl azodicarboxylate, azodicarboxamide, bisdialkylamide of azodicarboxylic acid or 1,1'-(azodicarbonyl)dialkyleneamine.

14. The method according to claim 1, wherein the azodicarboxylic acid derivative is methyl azodicarboxylate, ethyl azodicarboxylate, isopropyl azodicarboxylate, azodinitrile, azodicarboxamide, bisdimethylamide of azodicarboxylic acid, bisdiethylamide of azodicarboxylic acid, 1,1'-(azodicarbonyl)dipyrrolidine and 1,1'-(azodicarbonyl)dipiperidine.

15. The method according to claim 3, wherein the azodicarboxylic acid derivative is methyl azodicarboxylate, ethyl azodicarboxylate, isopropyl azodicarboxylate, azodinitrile, azodicarboxamide, bisdimethylamide of azodicarboxylic acid, bisdiethylamide of azodicarboxylic acid, 1,1'-(azodicarbonyl)dipyrrolidine and 1,1'-(azodicarbonyl)dipiperidine.

16. The method according to claim 4, wherein the azodicarboxylic acid derivative is methyl azodicarboxylate, ethyl azodicarboxylate, isopropyl azodicarboxylate, azodinitrile, azodicarboxamide, bisdimethylamide of azodicarboxylic acid, bisdiethylamide of azodicarboxylic acid, 1,1'-(azodicarbonyl)dipyrrolidine and 1,1'-(azodicarbonyl)dipiperidine.

17. The method according to claim 3,

wherein R.sup.1 and R.sup.2 are independently selected from the group consisting of hydrogen, phenyl, paranitrobenzyl, benzyl and alkyl substituted with a heterocyclic group, said heterocyclic group consisting of cephem ring, and a carbapenem ring; R.sup.3 is selected from the group consisting of t-butyl, phenylmethyl, pyrrolidinylmethyl, thienylmethyl, methyl substituted with a cephem ring, and methyl substituted with a carbapenem ring; and R.sup.4 is a carboxy protecting group.
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