Heptapeptide analogs of somatostatin

Details Heptapeptide analogs of somatostatin Heptapeptide analogs of somatostatin

C - Chemistry, Metallurgy

07

K

530/7.26, 167/10

C07K 14/655 (2006.01) A61K 38/00 (2006.01)

Patent

CA 1333647

Heptapeptide analogs of somatastatin which inhibit secretion of growth hormone. More particularly the invention relates to a heptapeptide of the formula A1 -A2 -A3 -A4 -A5 -Cys-A6 -A7, wherein A1 is SH-CH2-CH(Q)-CO- or SH-CH(Q)-CO- (where Q is H or a C1 -C8 alkyl group); A2 is o-, m-, or p- substituted X-Phe or D-X-Phe (where X is H, halogen, NH2, NO2, OH, C1 -C3 alkyl, or C1 -C3 alkoxy); A3 is X-Trp, D-X-Trp, .alpha.-N-methyl-X-Trp, or .alpha.-N-methyl-D-X-Trp (where X is a substituent on the benzene ring and is H, halogen, NH2, NO2, OH, C1 -C3 alkyl, or C1 -C3 alkoxy); A4 is Lys, .alpha.-N- methyl-Lys, or .epsilon.-N-R1 -Lys (where R1 is C1 -C3 alkyl); A5 is Val or Thr; A6 is Image where Z is H or CH3 and T is H, CH2OH, CH2CH2OH, CH2CH2CH2OH, CH(CH3)OH, isobutyl, benzyl (substituted in the o-, m, or p- positions with H, halogen, NH2, NO2, OH, C1 -C3 alkyl, or C1 -C3 alkoxy), CH2-.beta.-naphthyl (substituted on the naphthyl ring with H, halogen, NH2, NO2, OH, C1 -C3 alkyl, or C1 -C3, alkoxy), or CH2- pyridyl (substituted on the pyridyl ring with H, halogen, NH2, NO2, OH, C1 -C3 alkyl, or C1 -C3 alkoxy); and A7 is Image (where R2 is H or C1 -C3 alkyl), CH2OH, CH2OCR3 (where R3 is C1 -C3 alkyl, C8 -C12 aralkyl, or phenoxy), or Image (where R4 is H or C1 -C3 alkyl and R5 is H, C1 -C3 alkyl, phenyl, or C7 -C10 aralkyl); or a pharmaceutically acceptable salt thereof.

556023

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