Top > Search of International Patents > Cyclic peptide compound or pharmacologically acceptable salt thereof and method for producing same

Cyclic peptide compound or pharmacologically acceptable salt thereof and method for producing same commons

Foreign code F140007866
File No. KG0093-US01
Posted date May 7, 2014
Country United States of America
Application number 201113808772
Gazette No. 20130109833
Gazette No. 8653235
Date of filing Jul 6, 2011
Gazette Date May 2, 2013
Gazette Date Feb 18, 2014
International application number JP2011065521
International publication number WO2012005313
Date of international filing Jul 6, 2011
Date of international publication Jan 12, 2012
Priority data
  • P2010-155576 (Jul 8, 2010) JP
  • 2011WO-JP65521 (Jul 6, 2011) WO
Title Cyclic peptide compound or pharmacologically acceptable salt thereof and method for producing same commons
Abstract (US8653235)
Provided are a cyclic peptide compound or a pharmacologically acceptable salt thereof capable of inhibiting parakeratosis of skin, and a method for producing the same.
This method comprises subjecting a cyclic peptide compound of Formula (I): or a pharmacologically acceptable salt thereof, wherein Xaa1 and Xaa5 are each optionally substituted Ser, optionally substituted Thr, or optionally substituted Tyr; Xaa2 is optionally substituted Ile, optionally substituted Val, or optionally substituted Leu; Xaa3 and Xaa4 are each optionally substituted Asn, optionally substituted Gln, optionally substituted Asp, or optionally substituted Glu; and R1 is a group of Formula (II): -CO-(CH2)n-NH-(II), or Formula (III): -NH-(CH2)n-CO-(III), wherein n is the same as defined above, and in Formula (I), the linkage between Cys and Cys is a peptide bond or a disulfide bond, and the other linkages are peptide bonds, to cyclization with a compound of Formula (IV): Cys-R1-Xaa1-Xaa2-Xaa3-Xaa4-Xaa5-Cys(IV), wherein, Xaa1, Xaa2, Xaa3, Xaa4, Xaa5, and R1 are the same as defined above.
Scope of claims [claim1]
1. A cyclic peptide compound represented by Formula (I):

or a pharmacologically acceptable salt thereof, wherein Xaa1 and Xaa5 are each independently optionally substituted seryl, optionally substituted threonyl, or optionally substituted tyrosinyl;
Xaa2 is optionally substituted isoleucyl, optionally substituted valyl, or optionally substituted leucyl;
Xaa3 and Xaa4 are each independently optionally substituted asparaginyl, optionally substituted glutaminyl, optionally substituted aspartyl, or optionally substituted glutamyl;
Cys is cysteinyl; and
R1is a group represented by either Formula (II):
-- CO -- (CH2)n -- NH -- (II)
wherein n is an integer of 1 to 10, or Formula (III):
-- NH -- (CH2)n -- CO -- (III)
wherein n is an integer of 1 to 10; and in Formula (I), the linkage between Cys and Cys is a peptide bond or a disulfide bond, and the other linkages are peptide bonds.
[claim2]
2. The cyclic peptide compound or a pharmacologically acceptable salt thereof according to claim 1, wherein in Formula (I), Xaa1 is seryl, Xaa2 is isoleucyl, Xaa3 is glutamyl, Xaa4 is glutaminyl, Xaa5 is seryl, and R1 is a group represented by Formula (III) wherein n is 1.
[claim3]
3. The cyclic peptide compound or a pharmacologically acceptable salt thereof according to claim 1 or 2, wherein in Formula (I), Cys and Cys are linked through a disulfide bond.
[claim4]
4. A method for producing a cyclic peptide compound represented by Formula (I):

or a pharmacologically acceptable salt thereof, wherein Xaa1 and Xaa5 are each independently optionally substituted seryl, optionally substituted threonyl, or optionally substituted tyrosinyl;
Xaa2 is optionally substituted isoleucyl, optionally substituted valyl, or optionally substituted leucyl;
Xaa3 and Xaa4 are each independently optionally substituted asparaginyl, optionally substituted glutaminyl, optionally substituted aspartyl, or optionally substituted glutamyl;
Cys is cysteinyl; and
R1 is a group represented by either Formula (II):
-- CO -- (CH2)n -- NH -- (II),
wherein n is an integer of 1 to 10, or Formula (III):
-- NH -- (CH2)n -- CO -- (III)
wherein n is an integer of 1 to 10; and in Formula (I), the linkage between Cys and Cys is a peptide bond or a disulfide bond, and the other linkages are peptide bonds, the method comprising cyclizing a compound represented by Formula (IV):
Cys-R1-Xaa1-Xaa2-Xaa3-Xaa4-Xaa5-Cys (IV),
wherein Xaa1, Xaa2, Xaa3, Xaa4, Xaa5, Cys, and R1 are the same as Xaa1, Xaa2, Xaa3, Xaa4, Xaa5, Cys, and R1 of Formula (I).
[claim5]
5. The production method according to claim 4, wherein the cyclic peptide compound is a compound represented by Formula (I) wherein Xaa1 is seryl, Xaa2 is isoleucyl, Xaa3 is glutamyl, Xaa4 is glutaminyl, Xaa5 is seryl, and R1 is a group represented by Formula (III) wherein n is 1, and wherein a compound used as a starting material is a compound represented by Formula (IV) wherein Xaa1 is seryl, Xaa2 is isoleucyl, Xaa3 is glutamyl, Xaa4 is glutaminyl, Xaa5 is seryl, and R1 is a group represented by Formula (III).
[claim6]
6. The production method according to claim 4 or 5, wherein the cyclic peptide compound is a compound in which Cys and Cys of Formula (I) are linked through a disulfide bond, and wherein the cyclization is performed by oxidative crosslinking of the thiol groups of the cysteines at both ends of the compound represented by Formula (IV).
[claim7]
7. The cyclic peptide compound or a pharmacologically acceptable salt thereof according to claim 1, wherein in Formula (I), Xaa1 is seryl, Xaa2 is isoleucyl, Xaa3 is glutamyl, Xaa4 is glutaminyl, Xaa5 is seryl, and R1 is a group represented by Formula (III) wherein n is 5 or 8.
[claim8]
8. A pharmaceutical composition comprising the cyclic peptide compound or a pharmacologically acceptable salt thereof of claim 1 as an active ingredient, the pharmaceutical composition being in an oral dosage form.
[claim9]
9. A method for treating diseases or disorders induced by epimorphin or resulting from overexpression of epimorphin, comprising a step of administering orally the cyclic peptide compound or a pharmacologically acceptable salt thereof of claim 1 to a patient with disease or disorders induced by epimorphin or resulting from overexpression of epimorphin, wherein the disease or disorders induced by epimorphin or resulting from overexpression of epimorphin are chronic arteriosclerosis obliterans, Buerger's disease, or damaged organs.
[claim10]
10. The production method according to claim 4,
wherein the cyclic peptide compound is a compound represented by Formula (I) wherein Xaa1 is seryl, Xaa2 is isoleucyl, Xaa3 is glutamyl, Xaa4 is glutaminyl, Xaa5 is seryl, and R1 is a group represented by Formula (III) wherein n is 5 or 8, and
wherein a compound used as a starting material is a compound represented by Formula (IV) wherein Xaa1 is seryl, Xaa2 is isoleucyl, Xaa3 is glutamyl, Xaa4 is glutaminyl, Xaa5 is seryl, and R1 is a group represented by Formula (III).
  • Inventor, and Inventor/Applicant
  • HIRAI YOHEI
  • OKUGAWA YOJI
  • KWANSEI GAKUIN
IPC(International Patent Classification)
Please contact us by E-mail or facsimile if you have any interests on this patent.

PAGE TOP

close
close
close
close
close
close