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Novel derivatives of arginine vasopressin antagonists
| Details |
Inventors: Manning, Maurice; Sawyer, Wilbur H.;
Assignee: Medical College of Ohio (Toledo, OH); Trustees of Columbia University (New York, NY)
Primary Examiner: Phillips; Delbert R.
Assistant Examiner:
Attorney, Agent or Firm: Emch, Schaffer, Schaub & Porcello Co.
Compounds acting as antagonists of the antidiuretic/and or vasopressor activity of arginine vasopressin are those of the formula ##STR1## wherein n is 4 or 5; X is (D- or L-)Tyr(R), D-Phe, D-Val, D-Leu, D-Ile, D-Nva, D-Nle, D-Cha, D-Abu, D-Thr, D-Asn, D-Met or D-Gln; Y is Val, Ile, Thr, Ala, Lys, Cha, Nva, Met, Nle, Orn, Ser, Asn, Gln, Phe, Tyr, Gly, Abu or Leu; Z is (D- or L-) Arg, Orn or Lys; Q is Arg(NH.sub.2), Ser(NH.sub.2), (D- or L-)Ala(NH.sub.2), Gly, OH or NH.sub.2 and R is methyl, ethyl, propyl or butyl; provided that, when Y is Gln or Val, R may also be H. Further compounds are those wherein Q is NH(CH.sub.2).sub.3-6 NH.sub.2, NH(CH.sub.2).sub.2-6 OH, NHalk or NHbzl, provided that when Y is Val, Q is other than NHalk or NHbzl. Other compounds are those wherein Q is M-P, wherein M is Gly, (D- or L-)beta-Ala, (D- or L-)Ala, Sar, Orn, Val, Phe, Ile, Thr, Pro, Tyr, Arg or Ser and P is NHalk, NHbzl, NH(CH.sub.2).sub.2-6 OH, NH(CH.sub.2).sub.2-6 NH.sub.2 or OH, provided that when M is Gly, P is other than OH, and that when M is (D-or L-)beta-Ala, P is also NH.sub.2. Further compounds include decapeptides wherein Q is M-A-P', wherein M and A are selected independently from Gly, (D- or L-)beta-Ala, (D-or L-)Ala, Sar, Orn, Val, Phe, Ile, Thr, Pro, Tyr, Arg or Ser and P' is OH, NH.sub.2, NHalk, NH(CH.sub.2).sub.2-6 NH.sub.2, NHbzl or NH(CH.sub.2).sub.2-6 OH. Additional compounds include those wherein X is D-Tyr. |
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DETAILED DESCRIPTION Compounds of the invention, or comparison compounds of the prior art, are derivatives of arginine vasopressin.
Amino acids are in the L-form, unless otherwise indicated.
Each symbol, except for that of the 9-terminal substituent, is for the acyl (--C.
dbd.
O--) residue of the designated amino acid.
For example, 9-OH represents a compound with a completed --COOH group of the amino acid residue at the 8-position and is, therefore, a desglycinamide compound.
The correlation between full names and abbreviations is: AVP, arginine vasopressin; AVP-acid, deamido-arginine vasopressin, alternatively, vasopressinoic acid; desGly.
sup.
9 -AVP, 9-desglycine-argoinine vasopressin; desGly(NH.
sub.
2).
sup.
9 AVP, 9-desglycinamide-arginine vasopressin; d(CH.
sub.
2).
sub.
5 AVP, [1-(beta-mercapto-beta,beta-cyclopentamethylenepropionic acid)]-arginine vasopressin; d(CH.
sub.
2).
sub.
5 VDAVP, [1-(beta-mercapto-beta,beta-cyclopentamethylenepropionic acid), 4-valine, 8-D-arginine]vasopressin; d(CH.
sub.
2).
sub.
5 Tyr(Me)VDAVP, [1-(beta-mercapto-beta,beta-cyclopentamethylenepropionic acid), 2-O-methyltyrosine, 4-valine, 8-D-arginine]vasopressin; d(CH.
sub.
2).
sub.
5 -D-TyrVDAVP, [1-(beta-mercapto-beta,beta-cyclopentamethylenepropionic acid), 2-D-tyrosine, 4-valine, 8-D-arginine]vasopressin; d(CH.
sub.
2).
sub.
5 -D-TyrVAVP, [1-(beta-mercapto-beta,beta-cyclopentamethylenepropionic acid), 2-D-tyrosine, 4-valine]-arginine vasopressin; d(CH.
sub.
2).
sub.
5 Tyr(Me)AVP, [1-(beta-mercapto-beta,beta-cyclopentamethylenepropionic acid), 2-O-methyltyrosine]-arginine vasopressin; desGly.
sup.
9 d(CH.
sub.
2).
sub.
5 AVP, [1-(beta-mercapto-beta,beta-cyclopentamethylenepropionic acid), 9-desglycine]-arginine vasopressin; desGly(NH.
sub.
2).
sup.
9 d(CH.
sub.
2).
sub.
5 AVP, [1-(beta-mercapto-beta,beta-cyclopentamethylenepropionic acid), 9-desglycinamide]-arginine vasopressin; d(CH.
sub.
2).
sub.
5 [D-Phe.
sup.
2 ]VAVP, [1-(beta-mercapto-beta,beta-cyclopentamethylenepropionic acid), 2-D-phenylalanine, 4-valine]-arginine vasopressin; desGly.
sup.
9 d(CH
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I/O Systems 
