University of Toledo U.S. Patents

This collection includes United States patents for inventions by UT faculty, students and staff that list UT/MCO/MUO as the original assignee (owner). These patents include those assigned to the University of Toledo as well as to the Medical College of Ohio/Medical University of Ohio prior to the merger in 2006. Only granted patents, not patent applications, are included. Use the 'Search within this Series' box to search for keywords in the authors, titles, or abstracts of the patents.

The University of Toledo, Technology Transfer Website

Linear derivatives of arginine vasopressin antagonists
Compounds acting as antagonists of the antidiuretic/and or vasopressor activity of arginine vasopressin are those of the formula A--CH2 CO--D--Tyr(R)--Phe--Y--Asn--T--U--Z--Qwherein A is a-adamantyl, cyclohexyl, cyclopentyl, 1-mercaptocyclohexyl, 1-mercaptocyclopentyl, 1-ethyl-1-mercaptopropyl, yclohexylmethyl, cyclopentylmethyl, methyl, isopropyl, tert-butyl or phenyl; R is alkyl of 1-4 carbon atoms; Y is Val, Ile, Thr, Ala, Lys, Cha, Nva, Met, Nle, Orn, Ser, Asn, Gln, Phe, Tyr, Gly, Abu or Leu; T is Pen, Abu, Orn, Oys, Arg, Ala, Cha or Thr; U is Pro, Arg, Lys or Orn or a single bond; Z is (d-or L-) Arg, Orn or Lys and Q is Gly(NH2), Arg (NH2), Orn(NH2), Lys (NH2), (D- or L-)Ala(NH2), Ser(NH2), Val(NH2), Phe(NH2), Ile(NH2), Thr(NH2), Pro(NH2), Tyr(NH2), NH2, OH, NHR, NGbzl, NH(CH2)p NH2 or NH(CH2)p OH, wherein R is as above and p is an integer from 2 to 6. Compounds wherein T is Cys have similar activity.
Novel derivatives of arginine vasopressin antagonists
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(NH2), Ser(NH2), (D- or L-)Ala(NH2), Gly, OH or NH2 and R is methyl, ethyl, propyl or butyl; provided that, when Y is Gln or Val, R may also be H.
Novel derivatives of arginine vasopressin antagonists
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-lle, D-Nva, D-Nle, D-Cha, D-Abu, D-Thr, D-Asn, D-Met or D-Gln; Y is Val, lle, 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(NH2), Ser(NH2), (D- or L-)Ala(NH2), Gly, OH or NH2 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 Orn(NH2), NHCH2 CH2 NH2, Val(NH2), Phe(NH2), lle(NH2), Thr(NH2), Pro(NH2) or Tyr(NH2).
Antagonists of the antidiuretic action of arginine vasopressin
Compounds acting as antagonists of the antidiuretic activity of arginine vasopressin are those of the formula ##STR1## wherein X is (D- or L-)Tyr(R), D-Tyr, D-Phe, D-Val, D-Leu D-Ile, D-Arg, D-Gln, D-Asn, D-NVa, D-Nle, D-Cha, D-Abu, D-Thr or D-Met; R is methyl, ethyl, propyl or butyl and Z is D- or L-Arg. Also acting as antagonists of the antidiuretic action of arginine vasopressin are compounds of the formula ##STR2## wherein X and Z are as above and n is 4 or 5. Other antagonists of the antidiuretic action of arginine vasopressin are of the formula ##STR3## wherein X and n are as above and Z' is (D- or L-)Orn or (D- or L-)Lys. Other antagonists of the antidiuretic action of arginine vasopressin are of the formula ##STR4## wherein X is above, W is D-Pro, ?3 -Pro or HO-Pro; Z" is (D- or L-)Arg, (D- or L-)Lys or (D- or L-)Orn and n is 4 or 5; provided that when X is (D- or L-)Tyr(R) and n is 5, W is HO-Pro or D-Pro and that when X is D-Gln or D-Asn and n is 5, W is also Pro.
Novel antagonists of the antidiuretic and/or vasopressor action of arginine vasopressin
Compounds acting as antagonists of the antidiuretic activity of arginine vasopressin are those of the formula ##STR1## wherein X is methyl, ethyl, n-propyl, isopropyl or butyl; Tyr is D- or L-; W is Pro or ?3 -Pro; and Z is L- or D- Arg. Related compounds in which X is H, methyl or ethyl; W is Pro and Val at the 4-position is replaced by Gln- have antivasopressor activity against arginine vasopressin. Compounds wherein D-Tyr is unetherified (X is H), W- is Pro and Z- is D- or L-Arg also act as antagonists of the antidiuretic activity of arginine vasopressin.