U.S. patents available from 1976 to present.
U.S. patent applications available from 2005 to present.

Methods of making ureas and guanidines including, terazosin, prazosin, doxazosin, tiodazosin, trimazosin, quinazosin and bunazosin (exemplary of 2-substituted quinazoline compounds), and meobentine, and bethanidine and intermediates therefor

Patent 6080860 Issued on June 27, 2000. Estimated Expiration Date: Icon_subject September 29, 2017. Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.

Patent References

3511836

Substituted guanidine compounds as antifibrillatory agents
Patent #: 3949089
Issued on: 04/06/1976
Inventor: Maxwell ,   et al.

Antihypertensive agents
Patent #: 4026894
Issued on: 05/31/1977
Inventor: Winn ,   et al.

Cyanocarboxamidines and quinazoline process
Patent #: 4138561
Issued on: 02/06/1979
Inventor: Crenshaw ,   et al.

1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-tetrahydrofuroyl)piperazine hydrochloride dihydrate
Patent #: 4251532
Issued on: 02/17/1981
Inventor: Roteman

Substituted 5,6-dialkoxyquinazoline derivatives Patent #: 4672116
Issued on: 06/09/1987
Inventor: Bandurco ,   et al.

Inventors

Assignee

Application

No. 939414 filed on 09/29/1997

US Classes:

544/291, Nitrogen bonded directly at 2- and 4-positions540/575, The nitrogens are in the 1,4-positions of the hetero ring544/284, Additional nitrogen containing unsaturated hetero ring (e.g., thiazole, etc.)544/367, Ring chalcogen in the five-membered hetero ring544/374, Ring chalcogen in the additional hetero ring544/377, Plural ring chalcogens in the bicyclo ring system544/379, The additional hetero ring is five-membered and unsaturated (e.g., thienyl piperazines, etc.)544/388, Chalcogen or acyclic nitrogen bonded directly to at least one of the -C(=X) groups544/390, Halogen or acyclic nitrogen bonded directly to the -C(=X)- group558/385, Phosphorus attached indirectly to the cyano group by nonionic bonding558/386, Chalcogen, nitrogen, or halogen bonded directly to the phosphorus by nonionic bonding558/413, Sulfur, double bonded to oxygen, attached indirectly to the cyano group by nonionic bonding558/417The carbonyl is bonded directly to two non-carbon atoms, or to a non-carbon atom and an additional carbonyl (e.g., carbamates, oxamides, etc.)

Examiners

Primary: Raymond, Richard L.

Attorney, Agent or Firm

Foreign Patent References

  • 1056831 CA. 06/12/1979
  • 1057754 CA. 07/12/1979
  • 1081229 CA. 07/12/1980
  • 1390015 EP. 04/12/1975
  • 1464583 EP. 02/12/1977
  • 2041932 EP. 09/12/1980
  • 0034471 EP. 02/12/1981
  • 0227451 EP. 07/12/1987
  • 0227450 EP. 07/12/1987
  • 2231571 EP. 11/12/1990
  • 2350101 FR. 04/12/1975
  • 2321890 FR. 08/12/1975
  • 2457911 DE. 06/12/1975
  • 2707068 DE. 09/12/1977
  • 2725019 DE. 12/12/1977
  • 181743 HU. 12/12/1992
  • 1156973 GB. 08/12/1969
  • 1390015 GB. 04/12/1975
  • 1390014 GB. 04/12/1975
  • 2021108 GB. 05/12/1979
  • PCT/CA93/00355 WO. 08/12/1993

International Classes

C07C 275/70
C07D 407/04
C07D 241/04

Foreign Application Priority Data

1992-08-31 CA

Abstract

Novel methods for the synthesis of substituted ureas and guanidines including Terazosin, Prazosin, Doxazosin, Tiodazosin, Trimazosin, Quinasin and Bunazosin (exemplary of 2-amino substituted Quinazolines), Meobentine and Bethanidine and novel intermediates suitable for use in such methods of synthesis are taught.

Other References

  • Synthetic Communications, vol. 18, No. 5, May 1988, U.S. pp. 525-530, A.V.N. Reddy, et al.: An Efficient Synthesis of 3,4-dihydro-4-imino-2(1H)-quinazolines'
  • Houben-Weyl: `Methoden der Organischen Chemie`, Band E4, 1983, pp. 352-364, published by Georg Thieme Verlag, Stuttgart, DE
  • Houben-Weyl: 'Methoden der Organischen Chemie', Band E4, 1983, pp. 608-619, published by Georg Thieme Velag, Stuttgart, DE
  • Althius, T.H. and Hess, H.J., "Synthesis and Identification of the Major Metabolites of Prazosin Formed in Dog and Rat", Journal of Medicinal Chemistry vol. 20 p. 146 (1977)
  • Reiter, J. and Pongo, L, "On Triazoles. V[1,2],Synthesis of 1-and 2-R1 -3-R2,R3 -Amino-5-amino-1,2,4-triazoles", Journal of Heterocyclic Chemistry vol. 23, p. 401 (1986)
  • Curd, F.H.S., Landquist, J.K. and Rose, F.L., "Synthetic Animalarials, Part XXXII. 2-p-Chloroanilino-4-ଲ-di-ethylaminoethylaminoquinazolines containing Various Substituents in the Quinazoline Nucleus", Journal of the Chemical Society, p. 1759 (1948
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