Methods of preparing didesmethylsibutramine and other sibutramine derivatives
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07C-209/62
C07C-211/17
C07C-251/06
출원번호
US-0643941
(2003-08-20)
발명자
/ 주소
Senanayake, Chris Hugh
Han, Zhengxu
Krishnamurthy, Dhileepkumar
Pflum, Derek
출원인 / 주소
Sepracor Inc.
대리인 / 주소
Jones Day
인용정보
피인용 횟수 :
2인용 특허 :
33
초록▼
This invention encompasses novel methods of preparing sibutramine and sibutramine derivatives, and stereomerically pure sibutramine derivatives in particular. Examples of sibutramine derivatives include, but are not limited to, sibutramine metabolites such as desmethylsibutramine and didesmethylsibu
This invention encompasses novel methods of preparing sibutramine and sibutramine derivatives, and stereomerically pure sibutramine derivatives in particular. Examples of sibutramine derivatives include, but are not limited to, sibutramine metabolites such as desmethylsibutramine and didesmethylsibutramine. The invention further encompasses novel compounds useful in the synthesis of sibutramine derivatives.
대표청구항▼
1. A method of preparing a compound of Formula 1: or a pharmaceutically acceptable salt, solvate, clatbrate, hydrate, or prodrug thereof, wherein R1 is substituted or unsubstituted alkyl; and each R2 and R3 is independently hydrogen or substituted or unsubstituted alkyl, which comprises contacting a
1. A method of preparing a compound of Formula 1: or a pharmaceutically acceptable salt, solvate, clatbrate, hydrate, or prodrug thereof, wherein R1 is substituted or unsubstituted alkyl; and each R2 and R3 is independently hydrogen or substituted or unsubstituted alkyl, which comprises contacting a compound of Formula 2: wherein X is independently 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; with a reagent capable of cleaving a nitrogen-sulfur bond under conditions suitable for the formation of the compound of Formula 1. 2. The method of claim 1, wherein the compounds of formulas 1 and 2 are stereomerically pure.3. The method of claim 1, wherein the compound of Formula 1 is provided as a pharmaceutically acceptable salt.4. The method of claim 3, wherein the compound of Formula 1 is provided as an acetic, benzenesulfonic, benzoic, camphorsulfonic, citric, ethenesulfonic, fumaric, gluconic, glutamic, hydrobromic, hydrochloric, isethionic, lactic, maleic, malic, mandelic, methanesulfonic, mucic, nitric, pamoic, pantothenic, phosphoric, succinic, sulfuric, tartaric, or p-toluenesulfonic salt.5. The method of claim 1, wherein R1 is lower alkyl, optionally substituted with one or more hydroxyl groups.6. The method of claim 5, wherein R1 is CH2CH(CH3)(CH2OR4), CH(OCH2OCH3)CH(CH3)2, CH2CH(CH3)2, CH2C(CH3)2OR4,or CH2C(OR4)(CH2OR4)CH3, wherein R4 is alkyl, heteroalkyl, heteroaryl, aryl, hydrogen, acyl, carbonate, carbamate, ester, or urea.7. The method of claim 1, wherein R2 is not the same as R3.8. The method of claim 1, wherein R2 and R3 are both hydrogen.9. The method of claim 1, wherein R2 is methyl and R3 is hydrogen.10. The method of claim 1, wherein X is substituted or unsubstituted aralkyl, substituted or unsubstituted heterocycle, substituted or unsubstituted heteroalkyl, or substituted or unsubstituted heteroaryl.11. The method of claim 1, wherein X is alkyl.12. The method of claim 1, wherein x is aryl.
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