The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.
The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.
Patent No.:
Date of Patent:
Feb. 19, 2013
Filed:
May. 04, 2009
Divya Lal Saksena, Mumbai, IN;
Digamber Shripati Pawar, Mumbai, IN;
Nikhil Umesh Mohe, Mumbai, IN;
Nilesh Dagdu Patil, Mumbai, IN;
Chandrakesan Muralidharan, Mumbai, IN;
Lester Lobo, Mumbai, IN;
Radhakrishnan Venkatasubramanian Tarur, Mumbai, IN;
Divya Lal Saksena, Mumbai, IN;
Digamber Shripati Pawar, Mumbai, IN;
Nikhil Umesh Mohe, Mumbai, IN;
Nilesh Dagdu Patil, Mumbai, IN;
Chandrakesan Muralidharan, Mumbai, IN;
Lester Lobo, Mumbai, IN;
Radhakrishnan Venkatasubramanian Tarur, Mumbai, IN;
USV, Ltd., Mumbai, IN;
Abstract
This invention relates a process for preparing octreotide and derivatives thereof. The starting material, Cys(Trt)-2-Chlorotrityl resin is coupled with various amino acids to obtain a protected heptapeptide of formula (2): Boc-D-Phe-Cys(Trt)-Phe-D-Trp-Lys(Boc)-Thr(OBut)-Cys(Trt)-2-Chlorotrityl resin. The linear protected peptide of formula (2) is cleaved from the support using TFA5TIS and water to yield linear protected peptide of formula (3) Boc-D-Phe-Cys(Trt)-Phe-D-Trp-Lys(Boc)-Thr(OBut)-Cys(Trt)-OH Linear protected heptapeptide of formula (3) is deprotected to yield heptapeptide of formula (6): D-Phe-Cys-Phe-D-Tip-Lys-Thr-Cys-OH; which is cyclized using hydrogen peroxide and to the cyclic peptide of formula (7) D-Phe-Cys-Phe-D-Trp-Lys-Thr-Cys-OH; threoninol is coupled at C terminal to yield octreotide. Alternatively threoninol is coupled to the heptapeptide of formula (3) to yield protected octapeptide of formula (4) Boc-D-Phe-Cys(Trt)-Phe-D-Trp-Lys(Boc)-Thr(OBut)-Cys(Trt)-Thr-OL which is subsequently deprotected to yield linear octapeptide of formula (5) D-Phe-Cys-Phe-D-Trp-Lys-Thr-Cys-Thr-OL and cyclized with hydrogen peroxide to yield cyclic octreotide with a yield of >95%.