IP Library › Granted Patent US 7,811,989

Granted Patent B2

US 7,811,989 · App. 10/542,227 · Granted Oct 12, 2010

Peptide YY analogs

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Quick Facts

Patent No.: US 7,811,989
App. No.: 10/542,227
Granted: Oct 12, 2010
Kind: B2

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Abstract

The invention provides analogs of PYY. The invention also provides compositions and methods useful for controlling biological activities such as cell proliferation, nutrient transport, lipolysis, and intestinal water and electrolyte secretion.

Claims (170)

1. A compound wherein said compound is:

((2,3,4,5,6-F)Phe 20 )hPYY(3-36)NH 2 ; (SEQ ID NO. 31)

((2,3,4,5,6-F)Phe 21 )hPYY(3-36)NH 2 ; (SEQ ID NO. 32)

Ac-((2,3,4,5,6-F)Phe 26 )hPYY(22-36)NH 2 ; (SEQ ID NO. 33)

Ac-((2,3,4,5,6-F)Phe 26 )hPYY(24-36)NH 2 ; (SEQ ID NO. 34)

((2,3,4,5,6-F)Phe 26 )hPYY(3-36)NH 2 ; (SEQ ID NO. 35)

Ac-((2,3,4,5,6-F)Phe 27 )hPYY(22-36)NH 2 ; (SEQ ID NO. 36)

Ac-((2,3,4,5,6-F)Phe 27 )hPYY(24-36)NH 2 ; (SEQ ID NO. 37)

((2,3,4,5,6-F)Phe 27 )hPYY(3-36)NH 2 ; (SEQ ID NO. 38)

Ac-((2,3,4,5,6-F)Phe 36 )hPYY(22-36)NH 2 ; (SEQ ID NO. 39)

Ac-((2,3,4,5,6-F)Phe 36 )hPYY(24-36)NH 2 ; (SEQ ID NO. 40)

((2,3,4,5,6-F)Phe 36 )hPYY(3-36)NH 2 ; (SEQ ID NO. 41)

((3,4,5-F)Phe 20 )hPYY(3-36)NH 2 ; (SEQ ID NO. 42)

((3,4,5-F)Phe 21 )hPYY(3-36)NH 2 ; (SEQ ID NO. 43)

Ac-((3,4,5-F)Phe 26 )hPYY(22-36)NH 2 ; (SEQ ID NO. 44)

Ac-((3,4,5-F)Phe 26 )hPYY(24-36)NH 2 ; (SEQ ID NO. 45)

((3,4,5-F)Phe 26 )hPYY(3-36)NH 2 ; (SEQ ID NO. 46)

Ac-((3,4,5-F)Phe 27 )hPYY(22-36)NH 2 ; (SEQ ID NO. 15)

Ac-((3,4,5-F)Phe 27 )hPYY(24-36)NH 2 ; (SEQ ID NO. 47)

((3,4,5-F)Phe 27 )hPYY(3-36)NH 2 ; (SEQ ID NO. 12)

Ac-((3,4,5-F)Phe 36 )hPYY(22-36)NH 2 ; (SEQ ID NO. 48)

Ac-((3,4,5-F)Phe 36 )hPYY(24-36)NH 2 ; (SEQ ID NO. 49)

((3,4,5-F)Phe 36 )hPYY(3-36)NH 2 ; (SEQ ID NO. 50)

Ac-(D2Pal 26 )hPYY(22-36)NH 2 ; (SEQ ID NO. 26)

Ac-(2Pal 26 )hPYY(22-36)NH 2 ; (SEQ ID NO. 27)

Ac-(2Pal 26 , Leu 31 )hPPY(24-36)NH 2 ; (SEQ ID NO. 18)

Ac-(3Pal 26 )hPYY(22-36)NH 2 ; (SEQ ID NO. 14)

(3Pal 26 )hPYY(3-36)NH 2 ; (SEQ ID NO. 5)

Ac-(3Pal 26 , Leu 31 )hPPY(24-36)NH 2 ; (SEQ ID NO. 16)

Ac-(4Pal 26 )hPYY(22-36)NH 2 ; (SEQ ID NO. 13)

Ac-(4Pal 26 , Leu 31 )hPPY(24-36)NH 2 ; (SEQ ID NO. 17)

Ac-(A5c 22 )hPYY(22-36)NH 2 (SEQ ID NO. 4)

Ac-(A5c 31 )hPYY(22-36)NH 2 ; (SEQ ID NO. 24)

Ac-(A5c 31 )hPYY(24-36)NH 2 ; (SEQ ID NO. 51)

(A5c 31 )hPYY(3-36)NH 2 (SEQ ID NO. 3)

(A6c 10 )hPYY(3-36)NH 2 ; (SEQ ID NO. 52)

(A6c 11 )hPYY(3-36)NH 2 ; (SEQ ID NO. 53)

(A6c 12 )hPYY(3-36)NH 2 ; (SEQ ID NO. 54)

(A6c 13 )hPYY(3-36)NH 2 ; (SEQ ID NO. 55)

(A6c 15 )hPYY(3-36)NH 2 ; (SEQ ID NO. 56)

(A6c 16 )hPYY(3-36)NH 2 ; (SEQ ID NO. 57)

(A6c 17 )hPYY(3-36)NH 2 ; (SEQ ID NO. 58)

(A6c 18 )hPYY(3-36)NH 2 ; (SEQ ID NO. 59)

(A6c 20 )hPYY(3-36)NH 2 ; (SEQ ID NO. 60)

(A6c 21 )hPYY(3-36)NH 2 ; (SEQ ID NO. 61)

Ac-(A6c 22 )hPYY(22-36)NH 2 ; (SEQ ID NO. 62)

(A6c 22 )hPYY(3-36)NH 2 ; (SEQ ID NO. 63)

Ac-(A6c 24 )hPYY(22-36)NH 2 ; (SEQ ID NO. 25)

Ac-(A6c 24 )hPYY(24-36)NH 2 ; (SEQ ID NO. 64)

(A6C 24 )hPYY(3-36)NH 2 ; (SEQ ID NO. 10)

Ac-(A6c 24 , Leu 31 )hPYY(24-36)NH 2 ; (SEQ ID NO. 28)

Ac-(A6c 27 )hPYY(22-36)NH 2 ; (SEQ ID NO. 65)

Ac-(A6c 27 )hPYY(24-36)NH 2 ; (SEQ ID NO. 66)

(A6c 27 )hPYY(3-36)NH 2 ; (SEQ ID NO. 67)

Ac-(A6c 28 )hPYY(22-36)NH 2 ; (SEQ ID NO. 23)

Ac-(A6c 28 )hPYY(24-36)NH 2 ; (SEQ ID NO. 68)

(A6c 28 )hPYY(3-36)NH 2 ; (SEQ ID NO. 8)

Ac-(A6c 28 , Leu 31 )hPYY(24-36)NH 2 ; (SEQ ID NO. 29)

Ac-(A6c 29 )hPYY(22-36)NH 2 ; (SEQ ID NO. 69)

Ac-(A6c 29 )hpYY(24-36)NH 2 ; (SEQ ID NO. 70)

(A6c 29 )hPYY(3-36)NH 2 ; (SEQ ID NO. 71)

(A6c 3 )hPYY(3-36)NH 2 ; (SEQ ID NO. 72)

Ac-(A6c 30 )hPYY(22-36)NH 2 ; (SEQ ID NO. 22)

Ac-(A6c 30 )hPYY(24-36)NH 2 ; (SEQ ID NO. 73)

(A6c 30 )hPYY(3-36)NH 2 ; (SEQ ID NO. 9)

Ac-(A6c 31 )hPYY(22-36)NH 2 ; (SEQ ID NO. 21)

Ac-(A6c 31 )hPYY(24-36)NH 2 ; (SEQ ID NO. 30)

(A6c 31 )hPYY(3-36)NH 2 ; (SEQ ID NO. 74)

Ac-(A6c 32 )hPYY(22-36)NH 2 ; (SEQ ID NO. 75)

Ac-(A6c 32 )hPYY(24-36)NH 2 ; (SEQ ID NO. 76)

(A6c 32 )hPYY(3-36)NH 2 ; (SEQ ID NO. 77)

(A6c 6 )hPYY(3-36)NH 2 ; (SEQ ID NO. 78)

(A6c 7 )hPYY(3-36)NH 2 ; (SEQ ID NO. 79)

(A6c 9 )hPYY(3-36)NH 2 ; (SEQ ID NO. 80)

(Act 12 )hPYY(3-36)NH 2 ; (SEQ ID NO. 81)

(Act 13 )hPYY(3-36)NH 2 ; (SEQ ID NO. 82)

Ac-(Act 23 )hPYY(22-36)NH 2 ; (SEQ ID NO. 83)

(Act 23 )hPYY(3-36)NH 2 ; (SEQ ID NO. 84)

Ac-(Act 32 )hPYY(22-36)NH 2 ; (SEQ ID NO. 85)

Ac-(Act 32 )hPYY(24-36)NH 2 ; (SEQ ID NO. 86)

(Act 32 )hPYY(3-36)NH 2 ; (SEQ ID NO. 87)

(Act 7 )hPYY(3-36)NH 2 ; (SEQ ID NO. 88)

Ac-(Aib 22 )hPYY(22-36)NH 2 ; (SEQ ID NO. 89)

(Aib 22 )hPYY(3-36)NH 2 ; (SEQ ID NO. 11)

(Apc 19 )hPYY(3-36)NH 2 ; (SEQ ID NO. 90)

Ac-(Apc 25 )hPYY(22-36)NH 2 ; (SEQ ID NO. 91)

Ac-(Apc 25 )hPYY(24-36)NH 2 ; (SEQ ID NO. 92)

(Apc 25 )hPYY(3-36)NH 2 ; (SEQ ID NO. 93)

Ac-(Apc 26 )hPYY(22-36)NH 2 ; (SEQ ID NO. 94)

Ac-(Apc 26 )hPYY(24-36)NH 2 ; (SEQ ID NO. 95)

(Apc 26 )hPYY(3-36)NH 2 ; (SEQ ID NO. 96)

Ac-(Apc 33 )hPYY(22-36)NH 2 ; (SEQ ID NO. 97)

Ac-(Apc 33 )hPYY(24-36)NH 2 ; (SEQ ID NO. 98)

(Apc 33 )hPYY(3-36)NH 2 ; (SEQ ID NO. 99)

Ac-(Apc 34 )hPYY(22-36)NH 2 ; (SEQ ID NO. 100)

Ac-(Apc 34 )hPYY(24-36)NH 2 ; (SEQ ID NO. 101)

(Apc 34 )hPYY(3-36)NH 2 ; (SEQ ID NO. 102)

Ac-(Apc 35 )hPYY(22-36)NH 2 ; (SEQ ID NO. 103)

Ac-(Apc 35 )hPYY(24-36)NH 2 ; (SEQ ID NO. 104)

(Apc 35 )hPYY(3-36)NH 2 ; (SEQ ID NO. 7)

Ac-(Apc 36 )hPYY(22-36)NH 2 ; (SEQ ID NO. 105)

Ac-(Apc 36 )hPYY(24-36)NH 2 ; (SEQ ID NO. 106)

(Apc 36 )hPYY(3-36)NH 2 ; (SEQ ID NO. 107)

(Apc 4 )hPYY(3-36)NH 2 ; (SEQ ID NO. 108)

(Taz 26 )hPYY(3-36)NH 2 ; (SEQ ID NO. 6)

Ac-(Taz 26 )hPYY(22-36)NH 2 ; or (SEQ ID NO. 20)

Ac-(Taz 26 , Leu 31 )hPPY(24-36)NH 2 ; (SEQ ID NO. 19) or a pharmaceutically acceptable salt thereof.

2. A compound according to claim 1 , wherein said compound is:

[A5C 31 ]hPYY(3-36)NH 2 (SEQ ID NO. 3)

Ac-[A5C 22 ]hPYY(22-36)NH 2 (SEQ ID NO. 4)

[3Pal 26 ]hPYY(3-36)NH 2 ; (SEQ ID NO. 5)

[Taz 26 ]hPYY(3-36)NH 2 ; (SEQ ID NO. 6)

[Apc 35 ]hPYY(3-36)NH 2 ; (SEQ ID NO. 7)

[A6C 28 ]hPYY(3-36)NH 2 ; (SEQ ID NO. 8)

[A6C 30 ]hPYY(3-36)NH 2 ; (SEQ ID NO. 9)

[A6C 24 ]hPYY(3-36)NH 2 ; (SEQ ID NO. 10)

[Aib 22 ]hPYY(3-36)NH 2 ; (SEQ ID NO. 11)

[((3,4,5-F)Phe) 27 ]hPYY(3-36)NH 2 ; (SEQ ID NO. 12)

Ac-[4Pal 26 ]hPYY(22-36)NH 2 ; (SEQ ID NO. 13)

Ac-[3Pal 26 ]hPYY(22-36)NH 2 ; (SEQ ID NO. 14)

Ac-[((3,4,5-F)Phe) 27 ]hPYY(22-36)NH 2 ; (SEQ ID NO. 15)

Ac-(3Pal 26 , Leu 31 )hPPY(24-36)NH 2 ; (SEQ ID NO. 16)

Ac-(4Pal 26 , Leu 31 )hPPY(24-36)NH 2 ; (SEQ ID NO. 17)

Ac-(2Pal 26 , Leu 31 )hPPY(24-36)NH 2 ; (SEQ ID NO. 18)

Ac-(Taz 26 , Leu 31 )hPPY(24-36)NH 2 ; (SEQ ID NO. 19)

Ac-[Taz 26 ]hPYY(22-36)NH 2 ; (SEQ ID NO. 20)

Ac-[A6c 31 ]hPYY(22-36)NH 2 ; (SEQ ID NO. 21)

Ac-[A6c 30 ]hPYY(22-36)NH 2 ; (SEQ ID NO. 22)

Ac-[A6c 28 ]hPYY(22-36)NH 2 ; (SEQ ID NO. 23)

Ac-[A5c 31 ]hPYY(22-36)NH 2 ; (SEQ ID NO. 24)

Ac-[A6C 24 ]hPYY(22-36)NH 2 ; (SEQ ID NO. 25)

Ac-[D2Pal 26 ]hPYY(22-36)NH 2 ; (SEQ ID NO. 26)

Ac-[2Pal 26 ]hPYY(22-36)NH 2 ; (SEQ ID NO. 27)

Ac-[A6C 24 , Leu 31 ]hPYY(24-36)NH 2 ; (SEQ ID NO. 28)

Ac-[A6C 28 , Leu 31 ]hPYY(24-36)NH 2 ; (SEQ ID NO. 29)

Ac-[A6C 31 ]hPYY(24-36)NH 2 ; or (SEQ ID NO. 30)

Ac-(A6c 24 )hPYY(24-36)NH 2 ; (SEQ ID NO. 64) or a pharmaceutically acceptable salt thereof.

3. A compound according to claim 2 , wherein said compound is:

[A5C 31 ]hPYY(3-36)NH 2 (SEQ ID NO. 3)

[3Pal 26 ]hPYY(3-36)NH 2 ; (SEQ ID NO. 5)

[Taz 26 ]hPYY(3-36)NH 2 ; (SEQ ID NO. 6)

[A6C 28 ]hPYY(3-36)NH 2 ; (SEQ ID NO. 8)

[A6C 24 ]hPYY(3-36)NH 2 ; (SEQ ID NO. 10)

[Aib 22 ]hPYY(3-36)NH 2 ; (SEQ ID NO. 11)

[((3,4,5-F)Phe) 27 ]hPYY(3-36)NH 2 ; (SEQ ID NO. 12)

Ac-[4Pal 26 ]hPYY(22-36)NH 2 ; (SEQ ID NO. 13)

Ac-[3Pal 26 ]hPYY(22-36)NH 2 ; (SEQ ID NO. 14)

Ac-(3Pal 26 , Leu 31 )hPPY(24-36)NH 2 ; or (SEQ ID NO. 16)

Ac-(4Pal 26 , Leu 31 )hPPY(24-36)NH 2 ; (SEQ ID NO. 17) or a pharmaceutically acceptable salt thereof.

4. A compound according to claim 2 , wherein said compound is:

[A5C 31 ]hPYY(3-36)NH 2 (SEQ ID NO. 3)

[3Pal 26 ]hPYY(3-36)NH 2 ; (SEQ ID NO. 5)

[Taz 26 ]hPYY(3-36)NH 2 ; (SEQ ID NO. 6)

[Apc 35 ]hPYY(3-36)NH 2 ; (SEQ ID NO. 7)

[A6C 28 ]hPYY(3-36)NH 2 ; (SEQ ID NO. 8)

[A6C 24 ]hPYY(3-36)NH 2 ; (SEQ ID NO. 10)

[Aib 22 ]hPYY(3-36)NH 2 ; (SEQ ID NO. 11)

Ac-[4Pal 26 ]hPYY(22-36)NH 2 ; (SEQ ID NO. 13)

Ac-[3Pal 26 ]hPYY(22-36)NH 2 ; (SEQ ID NO. 14)

Ac-(3Pal 26 , Leu 31 )hPPY(24-36)NH 2 ; or (SEQ ID NO. 16)

Ac-(4Pal 26 , Leu 31 )hPPY(24-36)NH 2 ; (SEQ ID NO. 17) or a pharmaceutically acceptable salt thereof.

5. A compound according to claim 2 , wherein said compound is:

[A5C 31 ]hPYY(3-36)NH 2 (SEQ ID NO. 3)

[3Pal 26 ]hPYY(3-36)NH 2 ; (SEQ ID NO. 5)

[A6C 28 ]hPYY(3-36)NH 2 ; (SEQ ID NO. 8)

[A6C 24 ]hPYY(3-36)NH 2 ; (SEQ ID NO. 10)

Ac-[4Pal 26 ]hPYY(22-36)NH 2 ; or (SEQ ID NO. 13)

Ac-(A6c 24 )hPYY(24-36)NH 2 ; (SEQ ID NO. 64) or a pharmaceutically acceptable salt thereof.

6. A pharmaceutical composition comprising a compound according to any one of claims 1 - 5 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

7. A method of decreasing excess intestinal water and electrolyte secretion in a mammal in need thereof, said method comprising administering to said mammal an effective amount of a compound according to any one of claims 1 - 5 , or a pharmaceutically acceptable salt thereof.

Assignments (5)

CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNOR NAME PREVIOUSLY RECORDED ON REEL 296336 FRAME 0777. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jan 5, 2016

From: SOCIETE DE CONSEILS DE RECHERCHES ET D'APPLICATIONS SCIENTIFIQUES, S.A.S.

To: IPSEN PHARMA S.A.S.

Reel/Frame 037430/0194 →

CORRECTIVE ASSIGNMENT TO CORRECT THE ADDRESS PREVIOUSLY RECORDED ON REEL 023034 FRAME 0251. ASSIGNOR(S) HEREBY CONFIRMS THE ADDRESS SHOULD BE 65 QUAI GEORGES GORSE, 92100 BOULOGNE-BILLANCOURT, FRANCE. Recorded Jan 16, 2013

From: SOCIETE DE CONSEILS DE RECHERCHES ET D'APPLICATION SCIENTIFIQUES (S.C.R.A.S.)

To: IPSEN PHARMA S.A.S.

Reel/Frame 029636/0777 →

CHANGE OF NAME Recorded Jul 31, 2009

From: SOCIETE DE CONSEILS DE RECHERCHES ET D'APPLICATION SCIENTIFIQUES (S.C.R.A.S.)

To: IPSEN PHARMA S.A.S.

Reel/Frame 023034/0251 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 3, 2005

From: BIOMEASURE, INCORPORATED

To: SOCIETE DE CONSEILS DE RECHERCHES ET D'APPLICATIONS SCIENTIFIQUES, S.A.S.

Reel/Frame 017291/0302 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 22, 2005

From: DONG, ZHENG XIN

To: BIOMEASURE, INCORPORATED

Reel/Frame 017010/0329 →