IP Library Granted Patent US 7,572,883
Granted Patent B2
US 7,572,883 · App. 11/434,273 · Granted Aug 11, 2009

Somatostatin-dopamine chimeric analogs

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Quick Facts
Patent No.
US 7,572,883
App. No.
11/434,273
Granted
Aug 11, 2009
Kind
B2
Abstract

Disclosed is a series of somatostatin-dopamine chimeric analogs which retain both somatostatin and dopamine activity in vivo. An example is: 6-n-propyl-8β-ergolinglmethylthioacetyl-D-Phe-c(Cys-Tyr-D-Trp-Lys-Abu-Cys)-Thr-NH 2

Claims (34)

1. A compound of the formula (II),

wherein:

X is H, Cl, Br, I, F, —CN, or C 1-5 alkyl;

R1 is C 1-4 alkyl, H, allyl, alkenyl or —CN;

R2 and R3, each are, independently H or absent, provided that R2 and R3 are not both absent;

R4 is H or —CH 3 ;

R5 is C 1-5 alkyl group, or a group of the formula of —(CH 2 ) r N(CH 3 ) q ;

Y is —O—, —C(O)—, —S—, —SC(O)—, —OC(O)—, —N(R6)-C(O)—, —N(R7)-, or —N(R8)-(CH 2 ) s —C(O)—;

R6, R7, R8, R9 and R10 each is, independently, H or C 1-5 alkyl;

L is —(CH 2 ) p —C(O)—, when Y is —S—, —O— or —N(R7)-;

L is —C(O)—(CR9R10) q -C(O)—, when Y is —N(R7)-, —O—, or —S—;

L is -(Doc) t -, when Y is —C(O)—, SC(O)—, —OC(O)—, —N(R8)-(CH 2 ) s -C(O)—, or —N(R6)-C(O)—;

m is 0 or 1;

n is 2-10;

r is 1-8;

q is 2-4;

p is 1-10;

s is 1-10;

t is 1-10; and

z is somatostatin analog or a moiety comprising —H, —OH, (C 1 -C 6 )alkoxy, arylalkoxy, —NH 2 , or —NR9R10;

or a pharmaceutically acceptable salt thereof.

2. A compound of the formula:

or a pharmaceutically acceptable salt thereof.

3. A compound according to the formula:

or a pharmaceutically acceptable salt thereof.

4. A compound according to the formula:

Ethyl-[6-methyl-8β-ergolinylmethyl]thioacetate;

Ethyl-(6-n-propyl-8β-ergolinyl)methylthioacetate; or

or a pharmaceutically acceptable salt thereof.

5. A pharmaceutical composition comprising a compound according to any of claims 1 - 4 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

6. A compound according to claim 1 , wherein z is a moiety comprising —H, —OH, (C 1 -C 6 )alkoxy, arylalkoxy, —NH 2 , or —NR9R10; or a pharmaceutically acceptable salt thereof.

7. A compound according to claim 6 , wherein z is a moiety comprising —H, —OH, (C 1 -C 6 )alkoxy, or benzyl; or a pharmaceutically acceptable salt thereof.

8. A compound according to claim 6 , wherein said compound is according to the formula:

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 Jun 26, 2006
From: BIOMEASURE, INCORPORATED
To: SOCIETE DE CONSEILS DE RECHERCHES ET D'APPLICATIONS SCIENTIFIQUES, S.A.S.
Reel/Frame 018033/0579 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 20, 2006
From: CULLER, MICHAEL DEWITT; DONG, ZHENG XIN; KIM, SUN H.; MOREAU, JACQUES-PIERRE
To: BIOMEASURE, INCORPORATED
Reel/Frame 018008/0285 →