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US 2006/0128767 A1Published application
Methods of preparing sulfinamides and sulfoxides
AssigneeApsinterm LLC
InventorsChris Senanayake, Zhengxu Han, Dhileepkumar Krishnamurthy, Derek Pflum, Harold Wilkinson
Life of this patent
Estimating the term…
Abstract
This invention encompasses novel methods of preparing sulfinamides and sulfoxides, particularly stereomerically pure sulfinamides and sulfoxides. The invention further encompasses novel compounds from which sulfinamides and sulfoxides can be prepared.
Claims30
A compound of Formula 3:
- wherein n is 0 to 3;
- L is COmR3 or SOmR3, wherein m is 0 to 3;
- R1 and R2 together form a cyclic structure or each of R1 and R2 is independently substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocycle;
- R1′ and R2′ together form a cyclic structure or each of R1′ and R2′ is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocycle;
- Ra and Rb together form a cyclic structure or each of Ra and Rb is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocycle;
- and R3 is a polymer bound alkyl, aryl or heteroalkyl, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted ether, substituted or unsubstituted ester, substituted or unsubstituted ketone, substituted or unsubstituted phosphonate, substituted or unsubstituted phosphonic acid ester, substituted or unsubstituted phosphinoyl, substituted or unsubstituted sulfide, substituted or unsubstituted sulfone, substituted or unsubstituted sulfinyl imine, substituted or unsubstituted heterocycle, or —NR4R5, wherein R4 and R5 together with the nitrogen atom to which they are attached form a heterocycle or each of R4 and R5 is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, substituted or unsubstituted ether, substituted or unsubstituted sulfide, or substituted or unsubstituted heterocycle.
3 more elements
A method of preparing pantoprazole or a derivative, prodrug, salt, solvate, clathrate, or stereomerically pure form thereof, which comprises contacting a compound of Formula 11:
- wherein R1 and R2 together form a cyclic structure or each of R1 and R2 is independently substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocycle;
- R1′ and R2′ together form a cyclic structure or each of R1′ and R2′ is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocycle;
- and Prot is a protecting group;
- with a compound of Formula 12:
- wherein M is Al, Ba, Li, Na, K, Mg, Mn, Zn, Cd, In, Cu, or is of the formula CdZ, BaZ, MgZ, ZnZ, AlZ2, MnZ, InZ, or CuZ, and Z is Cl, Br, L aryl, aralkyl, or heterocycle;
- under conditions suitable for the formation of a compound of Formula 13:
- and optionally contacting the compound of Formula 13 with a reagent capable of replacing Prot with a hydrogen atom or a cation.
4 more elements
A method of preparing lansoprazole or a derivative, prodrug, salt, solvate, clathrate, or stereomerically pure form thereof, which comprises contacting a compound of Formula 15:
- wherein R1 and R2 together form a cyclic structure or each of R1 and R2 is independently substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocycle;
- R1′ and R2′ together form a cyclic structure or each of R1′ and R2′ is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocycle;
- and Prot is a protecting group;
- with a compound of Formula 16:
- wherein M is Al, Ba, Li, Na, K, Mg, Mn, Zn, Cd, In, Cu, or is of the formula CdZ, BaZ, MgZ, ZnZ, AlZ2, MnZ, InZ, or CuZ, and Z is Cl, Br, L aryl, aralkyl, or heterocycle;
- under conditions suitable for the formation of a compound of Formula 17:
- and optionally contacting the compound of Formula 17 with a reagent capable of replacing Prot with a hydrogen atom or a cation.
4 more elements
A method of preparing omeprazole or a derivative, prodrug, salt, solvate, clathrate, or stereomerically pure form thereof, which comprises contacting a compound of Formula 19:
- wherein R1 and R2 together form a cyclic structure or each of R1 and R2 is independently substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocycle;
- R1′ and R2′ together form a cyclic structure or each of R1′ and R2′ is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocycle;
- and Prot is a protecting group;
- with a compound of Formula 20:
- wherein M is Al, Ba, Li, Na, K, Mg, Mn, Zn, Cd, In, Cu, or is of the formula CdZ, BaZ, MgZ, ZnZ, AlZ, MnZ, InZ′, or CuZ, and Z is Cl, Br, 1, aryl, aralkyl, or heterocycle;
- under conditions suitable for the formation of a compound of Formula 21:
- and optionally contacting the compound of Formula 21 with a reagent capable of replacing Prot with a hydrogen atom or a cation.
4 more elements
A method of preparing rabeprazole or a derivative, prodrug, salt, solvate, clathrate, or stereomerically pure form thereof, which comprises contacting a compound of Formula 15:
- wherein R1 and R2 together form a cyclic structure or each of R1 and R2 is independently substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocycle;
- R1′ and R2′ together form a cyclic structure or each of R1′ and R2′ is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocycle;
- and Prot is a protecting group;
- with a compound of Formula 23:
- wherein M is Al, Ba, Li, Na, K, Mg, Mn, Zn, Cd, In, Cu, or is of the formula CdZ, BaZ, MgZ, ZnZ, AlZ2, MnZ, InZ, or CuZ, and Z is Cl, Br, L aryl, aralkyl, or heterocycle;
- under conditions suitable for the formation of a compound of Formula 24:
- and optionally contacting the compound of Formula 24 with a reagent capable of replacing Prot with a hydrogen atom or a cation.
4 more elements
A compound of Formula 7:
- or a salt, solvate, clathrate, or stereomerically pure form thereof, wherein R3 is independently substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, substituted or unsubstituted ether, substituted or unsubstituted sulfide, substituted or unsubstituted heterocycle, or —NR4R5, wherein R4 and R5 together with the nitrogen atom to which they are attached form a heterocycle or each of R4 and R5 is independently hydrogen, is independently substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, substituted or unsubstituted ether, substituted or unsubstituted sulfide, or substituted or unsubstituted heterocycle;
- each R10 is independently substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, substituted or unsubstituted ether, substituted or unsubstituted sulfide, a primary, secondary, or tertiary amine, a heterocycle, or a halogen atom;
- n is an integer of 1 to 4;
- and m is an integer of 0 to 4.
1 more element
A compound of Formula 25:
- or a salt, solvate, clathrate, or stereomerically pure form thereof, wherein R1 and R2 together form a cyclic structure or each of R1 and R2 is independently substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocycle;
- R3 is substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, substituted or unsubstituted ether, substituted or unsubstituted sulfide, substituted or unsubstituted heterocycle, or —NR4R5, wherein R4 and R5 together with the nitrogen atom to which they are attached form a heterocycle or each of R4 and R5 is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, substituted or unsubstituted ether, substituted or unsubstituted sulfide, or substituted or unsubstituted heterocycle;
- each R11 is independently substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, substituted or unsubstituted ether, substituted or unsubstituted sulfide, a primary, secondary, or tertiary amine, a heterocycle, or a halogen atom;
- R12 is substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, substituted or unsubstituted ether, substituted or unsubstituted sulfide, or substituted or unsubstituted heterocycle, or is a sulfoxide;
- and r is an integer from 0 to 4.
2 more elements
Dependencies are inferred from the claim text.