Nitrogen Bonded Directly At 2- And 4-positions Patents (Class 544/291)
  • Patent number: 5064833
    Abstract: 2,4-diaminoquinazoline compounds are inhibitors of the H.sup.+ K.sup.+ ATPase enzyme and useful for the treatment of diseases of the stomach based on excessive gastric acid secretion. A compound of the invention is 2-[2-methyl-4-fluorophenyl)amino]-4-(N-methylphenylamino)quinazoline.
    Type: Grant
    Filed: May 8, 1990
    Date of Patent: November 12, 1991
    Assignee: Smithkline Beecham Intercredit B.V.
    Inventors: Robert J. Ife, Thomas H. Brown, Colin A. Leach, David J. Keeling
  • Patent number: 5053411
    Abstract: This invention pertains to novel substituted N-aryl-N-[4-(1-heterocyclicalkyl)piperidinyl]amides useful as analgesics, and methods of administering analgesia, which comprises the systemic administration to mammals of such compounds, and pharmaceutical compositions containing such compounds, wherein the novel compounds have the general formula: ##STR1## including optically active isomeric forms, and the pharmaceutically acceptable acid addition salts thereof, wherein R, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are defined in the disclosure.
    Type: Grant
    Filed: April 20, 1989
    Date of Patent: October 1, 1991
    Assignee: Anaquest, Inc.
    Inventors: Jerome R. Bagley, Nhora L. Lalinde, Bao-Shan Huang, H. Kenneth Spencer
  • Patent number: 4948797
    Abstract: 2,2-Disubstituted 2,3-dihydro-1,4-benzodioxin derivatives of formula (I): ##STR1## and pharmaceutically acceptable salts thereof having in vitro high affinity and selectively for .alpha..sub.1 receptors and in vivo good and long lasting hypotensive activty, with negligible side-effects; processes for the preparation thereof and pharmaceutical compositions therefrom.
    Type: Grant
    Filed: November 9, 1988
    Date of Patent: August 14, 1990
    Assignee: Istituto Luso Farmaco d'Italia S.p.A.
    Inventors: Elso Manghisi, Aldo Salimbeni
  • Patent number: 4873330
    Abstract: Anhydrous, stable, crystalline .delta.-form of prazosin hydrochloride, having an infrared spectrum in potassium bromide of FIG. 1 having the following sharp absorption bands at 7.95.mu., 13.3.mu., and a triplet at 9.95.mu. and the x-ray diffractogram of FIG. 2 having sharp bands in 10.5.degree., 12.0.degree., 16.9.degree., and doublets in 24.5.degree. and 26.5.degree.. The .delta.-form of prazosin hydrochloride is prepared by removing the water of crystallization of prazosin hydrochloride hydrate by azeotropic distillation with selected organic solvents having a boiling point in the range of 55.degree.-160.degree. C. The .delta.-form of prazosin hydrochlorie is useful as a hypotensive agent.
    Type: Grant
    Filed: February 8, 1988
    Date of Patent: October 10, 1989
    Assignee: Orion-yhtyma Oy
    Inventor: Stig O. E. Lindholm
  • Patent number: 4818753
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is H, methyl, ethyl, or chloro and R.sup.2 is hydrocarbyl of 1-12 C are useful as antifungal agents. Compounds of this series wherein R.sup.2 is 7-12 C are novel. A new synthetic method for the compounds is also described.
    Type: Grant
    Filed: September 18, 1987
    Date of Patent: April 4, 1989
    Assignee: SRI International
    Inventors: William T. Colwell, Joseph I. DeGraw
  • Patent number: 4816455
    Abstract: A new anhydrous crystalline form of prazosine hydrochloride characterized by the following bands in the infra-red spectrum in potassium bromide is described:3445 cm.sup.-1 (2.90 .mu.m),1010 cm.sup.-1 (9.90 .mu.m) (duplet), and768 cm.sup.-1 (13.03 .mu.m).This new form is distinguished by its surprisingly great stability in storage compared with known polymorphous forms of prazosine.
    Type: Grant
    Filed: March 3, 1987
    Date of Patent: March 28, 1989
    Assignee: Heumann Pharma GmbH & Co.
    Inventors: Helmut Schickaneder, Ingomar Grafe, Kurt H. Ahrens
  • Patent number: 4795750
    Abstract: Quinazoline compounds of the general formula (I): ##STR1## in which (a) R is a hydrogen atom and R.sub.1 is an -(2-pyrrolidinon-1-yl)-alkyl group,(b) R is a methyl group and R.sub.1 is an -(mono- or dialkoxyphenyl)-alkyl group, p0 (c) R together with R.sub.1 forms a piperidine ring substituted with 2-keto-1-benzimidazolinyl radical in the 4-position of the piperidine group ring; or(d) R together with R.sub.1 forms a piperazine ring substituted with a hydroxyacyl group in the 4-position of the piperazine ring.
    Type: Grant
    Filed: December 4, 1986
    Date of Patent: January 3, 1989
    Assignee: Gerot-Pharmazeutika Gesellschaft
    Inventor: Ludwig H. Schlager
  • Patent number: 4775673
    Abstract: Substituted acylpiperazinoquinazolines of formula I ##STR1## wherein n is 0 or 1, R represents an alkyl group with 1 to 4 carbon atoms or a benzyl group, and R.sub.1 is a hydrogen atom, a methyl group or a phenyl group. Addition salts of these compounds with inorganic and organic acids are also disclosed. The compounds possess a significant antihypertensive activity. They can be prepared by the reaction of 2-halogeno quinazoline derivatives with the corresponding acylpiperazines, followed (if required) by neutralization of the respective base with a suitable acid to form its pharmaceutically convenient addition salt.The acid addition salts, especially hydrochlorides, are readily soluble in water and give stable, almost neutral aqueous solutions which can be used in parenteral (injectable) and peroral medicinal dosage forms.
    Type: Grant
    Filed: April 14, 1986
    Date of Patent: October 4, 1988
    Assignee: SPOFA, spojene podniky pro zdravotnickou vyrobu
    Inventors: Jan Koenig, Miroslav Rajsner, Vaclav Trcka, Sverluse Macova
  • Patent number: 4749705
    Abstract: New quinazoline derivatives are disclosed, as represented by the following formula: ##STR1## wherein A is hydrogen atom or lower alkyloxy group; R.sub.4 is hydrogen atom, a lower alkyl, lower alkyloxy or a halogen atom group. Y is hydrogen atom, lower alkyloxy, sulfamoyl or Y and R.sub.4, taken together, are joined to form --O--CH.sub.2 --CH.sub.2 --O--; Z is a 4-oxopiperidino, 4-thioxopiperidino, 4-oximepiperidino, 4-O-loweralkyl-oxime-piperidino, 4-O-(3-lower alkyl-2-hydroxypropyl)-oxime-piperidino, 4-O-(3-lower alkylamino-2-hydroxypropyl)-oxime-piperidino or 4-O-(3-N'-lower alkyl, N'-benzylamino-2-hydroxypropyl)-oxime-piperidino group. These compounds are useful as anti-hypertensive agents.
    Type: Grant
    Filed: February 13, 1987
    Date of Patent: June 7, 1988
    Assignee: Kotobuki Seiyaku Co., Ltd.
    Inventors: Tsuyoshi Tomiyama, Tomoyuki Kawai, Yumiko Ichikawa
  • Patent number: 4739055
    Abstract: Anhydrous, stable, crystalline .delta.-form of prazosin hydrochloride, having an infrared spectrum in potassium bromide of FIG. 1 having the following sharp absorption bands at 7.95.mu., 13.3.mu. and a triplet at 9.95.mu. and the x-ray diffractogram of FIG. 2 having sharp bands in 10.5.degree., 12.0.degree., 16.9.degree. and doublets in 24.5.degree. and 26.5.degree.. The .delta.-form of prazosin hydrochloride is prepared by removing the water of crystallization of prazosin hydrochloride hydrate by azeotropic distillation with selected organic solvents having a boiling point in the range of 55.degree.-160.degree. C. The .delta.-form of prazosin hydrochloride is useful as a hypotensive agent.
    Type: Grant
    Filed: October 15, 1984
    Date of Patent: April 19, 1988
    Assignee: Orion-yhtyma Oy
    Inventor: Stig O. E. Lindholm
  • Patent number: 4677219
    Abstract: An improved process for the preparation of 6-substituted-5-alkyl-2,4-quinazolinediamines, useful in the production of trimetrexate and similar antifolate agents, together with several novel intermediates are disclosed.
    Type: Grant
    Filed: July 17, 1986
    Date of Patent: June 30, 1987
    Assignee: Warner-Lambert Company
    Inventors: Ellen M. Berman, Mark J. Suto
  • Patent number: 4672116
    Abstract: Quinazoline derivatives having an oxy substituent in 5 and 6 positions are described. The novel quinazoline derivatives are useful as cardiotonic agents.
    Type: Grant
    Filed: December 20, 1985
    Date of Patent: June 9, 1987
    Assignee: Ortho Pharmaceutical Corporation
    Inventors: Victor T. Bandurco, Stanley C. Bell, John H. Dodd, Robert Falotico, Charles F. Schwender, Alfonso J. Tobia
  • Patent number: 4647684
    Abstract: The invention relates to a new multistage process for the production of 4-amino-6,7-dimethoxy-2-[4-(furo-2-yl)-piperazin-1-yl]-quinazoline corresponding to the following formula ##STR1## and physiologically compatible salts thereof, which gives better yields and uses less expensive and more reactive materials than known processes. The intermediate product formed in this process, N"-cyano-N'-(3,4-dimethoxyphenyl)-O-phenylisourea, shows antihypertensive activity on its own.
    Type: Grant
    Filed: March 16, 1984
    Date of Patent: March 3, 1987
    Assignee: Ludwig Heumann & Co. GmbH
    Inventors: Helmut Schickaneder, Kurt H. Ahrens
  • Patent number: 4639453
    Abstract: New substituted 1-(4-amino-6,7-dialkoxyquinazolinyl)-4-cyclohexenyl derivatives of piperazine and homopiperazine, of the general formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5, which can be identical or different, denote hydrogen, straight-chain or branched alkyl groups with in each case 1 to 6 carbon atoms, cyclic aliphatic radicals with in each case 5 to 7 carbon atoms, aromatic radicals or substituted aromatic radicals, which can be monosubstituted or polysubstituted by identical or different substituents from the group comprising halogen and lower alkyl groups with in each case 1 to 4 carbon atoms in the alkyl part, or denote aralkyl radicals, furanyl radicals or thienyl radicals, orR.sup.2 and R.sup.3 together denote the group --(CH.sub.2).sub.a --, wherein a is the number 4 or 5, orR.sup.3 and R.sup.4 together denote the group --(CH.sub.2).sub.b --, wherein b is the number 3, 4 or 5,R.sup.6 and R.sup.
    Type: Grant
    Filed: December 7, 1984
    Date of Patent: January 27, 1987
    Assignee: Beiersdorf Aktiengesellschaft
    Inventor: Werner Hansen
  • Patent number: 4607034
    Abstract: There are presented novel quinazoline derivatives, namely 2-(4-substituted-carbamoyl-piperazin-1-yl)quinazoline derivatives, 2-(4-substituted-carbamoyl-homopiperazin-1-yl)quinazoline derivatives, 2-(4-substituted-thiocarbamoyl-piperazin-1-yl)quinazoline derivatives and 2-(4-substituted-thiocarbamoyl-piperazin-1-yl)quinazoline derivatives, having excellent antihypertensive activities.
    Type: Grant
    Filed: October 21, 1980
    Date of Patent: August 19, 1986
    Assignee: Mitsubishi Yuka Pharmaceutical Co., Ltd.
    Inventors: Susumu Mizogami, Hidetoshi Hiranuma, Tetsuo Sekiya, Mitsuo Hanazuka
  • Patent number: 4578389
    Abstract: The invention relates to quinazoline derivatives corresponding to the following general formula ##STR1## in which R is a mono- to trisubstituted 5-ring heterocycle from the group comprising triazoles, oxadiazoles, thiazoles and imidazoles, the heterocycle being attached to the piperazine or homopiperazine ring by a carbon atom, and n has a value of 2 or 3, or R represents an N-cyanophenyl imidocarbonate group, and to physiologically compatible salts thereof, to processes for their production and to medicaments containing these compounds.
    Type: Grant
    Filed: September 10, 1984
    Date of Patent: March 25, 1986
    Assignee: Ludwig Heumann & Co. GmbH
    Inventors: Helmut Schickaneder, Istvan Szeleny, Peter Morsdorf, Kurt H. Ahrens
  • Patent number: 4550164
    Abstract: Isobutylene carbonate and certain 1-substituted piperazine compounds are reacted in a process that forms 2-methyl-2-hydroxypropyl 4-substituted piperazine-1-carboxylate compounds which are medicinal agents or synthetic intermediates for such agents. The features of the process allow the preparation of an essentially pure 2-methyl-2-hydroxypropyl carboxylate compound.
    Type: Grant
    Filed: April 24, 1981
    Date of Patent: October 29, 1985
    Assignee: Pfizer Inc.
    Inventors: Irving M. Goldman, Donald E. Kuhla, Constantine Sklavounos
  • Patent number: 4543356
    Abstract: This invention is directed to new quinazoline derivatives of the following formula having use in the treatment of symptoms associated with allergic manifestations. ##STR1## wherein R.sub.a.sup.1 and R.sub.b.sup.1 are C.sub.2 -C.sub.7 alkoxycarbonyl or R.sub.a.sup.1 and R.sub.b.sup.1 is linked together to form a group of the formula: ##STR2## R.sup.2 and R.sup.3 are hydrogen, C.sub.1 -C.sub.6 alkyl, halogen, nitro, amino, C.sub.1 -C.sub.6 alkoxy, phenoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkylpiperazinyl, C.sub.1 -C.sub.18 alkanoylamino, di(C.sub.1 -C.sub.6)alkanoylamino, C.sub.3 -C.sub.9 alkoxalylamino, C.sub.4 -C.sub.8 cycloalkylcarbonylamino, C.sub.3 -C.sub.7 cycloalkyl(C.sub.1 -C.sub.6)alkanoylamino, benzamido, phenyl(C.sub.1 -C.sub.6)alkanoylamino, C.sub.1 -C.sub.6 alkylsulfonylamino or di(C.sub.1 -C.sub.6)alkylamino which may be substituted with hydroxy,A.sup.1 is a group of the formula: ##STR3## in which R.sup.4 is hydrogen C.sub.1 -C.sub.6 alkyl, hydroxy, C.sub.1 -C.sub.6 alkoxy, C.sub.
    Type: Grant
    Filed: January 3, 1983
    Date of Patent: September 24, 1985
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Ikuo Ueda, Masayuki Kato, Masanobu Nagano
  • Patent number: 4539323
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2, which may be identical to or different from each other, are each independently hydrogen, straight or branched alkyl of 1 to 8 carbon atoms or arylmethyl; orR.sub.1 and R.sub.2, together with each other, are --(CH.sub.2).sub.4 or --(CH.sub.2).sub.5 --; andR.sub.3 and R.sub.4, which may be identical to or different from each other, are each independently hydrogen, straight or branched alkyl of 1 to 4 carbon atoms or arylmethyl; orR.sub.3 and R.sub.4, together with each other, are --CH.sub.3 -- or --CH.sub.2 --CH.sub.2 --;and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful for the treatment of cardiovascular diseases, especially hypertension.
    Type: Grant
    Filed: September 14, 1983
    Date of Patent: September 3, 1985
    Assignee: Boehringer Ingelheim KG
    Inventors: Anton Mentrup, Ernst-Otto Renth, Kurt Schromm, Wolfgang Hoefke, Wolfram Gaida
  • Patent number: 4495188
    Abstract: Acylaminoquinazoline derivatives of formula ##STR1## (in which: R.sup.1 represents a lower alkoxy group, a substituted or unsubstituted lower alkyl group, a cycloalkyl group, a lower alkenyl group, a vinyl group having an optionally substituted phenyl or furyl substituent, an optionally substituted phenyl group, a furyl group, an oxazolyl group, a methylthiooxadiazolyl group or a tetrahydrofuryl group;R.sup.2 represents a hydrogen atom or a lower alkyl group;R.sup.3 represents a lower alkyl group or an optionally substituted phenyl group;R.sup.4 represents a hydrogen atom or an acyloxy-substituted phenyl group;X represents a methylene group or a sulphur atom; andn is 2 or 3)and pharmaceutically acceptable acid addition salts thereof are valuable antihypertensive agents and inhibit the activity of the angiotension I-converting enzyme.
    Type: Grant
    Filed: November 24, 1981
    Date of Patent: January 22, 1985
    Assignee: Sankyo Company Limited
    Inventors: Yasunobu Sato, Hiroshi Fukumi, Hiroyuki Koike, Nobuaki Kitahara
  • Patent number: 4440769
    Abstract: 4-amino-6,7-dimethoxy-2-(4-phenylalkanoylpiperazin-1-yl) quinazolines having .alpha..sub.1 -adrenergic receptor antagonistic activity. These compounds are useful in the treatment of hypertension.
    Type: Grant
    Filed: February 11, 1983
    Date of Patent: April 3, 1984
    Assignee: Abbott Laboratories
    Inventors: John F. DeBernardis, Martin Winn
  • Patent number: 4435401
    Abstract: 2,4-Diaminoquinazoline compounds of the formula ##STR1## or a pharmaceutically acceptable salt thereof wherein R is a pyrimidinyl, pyrazinyl, pyridazinyl or triazinyl group linked to the piperazine ring by one of its carbon atoms, and optionally substituted by hydroxy, halogen, alkyl, aralkyl, alkoxy, aralkoxy, alkylthio, aryl, aryloxy and certain amino groups; their use as an antihypertensive agent and pharmaceutical compositions containing them.
    Type: Grant
    Filed: December 23, 1981
    Date of Patent: March 6, 1984
    Assignee: Pfizer Inc.
    Inventors: Simon F. Campbell, Rhona M. Plews
  • Patent number: 4429126
    Abstract: Quinazoline derivatives of the formulae: ##STR1## wherein A.sup.1 is ##STR2## A.sup.2 is ##STR3## R.sup.1 is hydrogen, carboxy or esterified carboxy, R.sub.a.sup.1 and R.sub.b.sup.1 are esterified carboxy,R.sup.2 and R.sup.3 are hydrogen, alkyl, halogen, nitro, amino, alkoxy, aryloxy, alkylthio, alkylpiperazinyl, acylamino or dialkylamino which may be substituted with hydroxy,R.sup.4 is hydrogen, alkyl, hydroxy, alkoxy, alkenyloxy, dialkylamino or 2,2-dialkoxycarbonylvinylaminoR.sub.a.sup.4 is hydrogen, alkyl, hydroxy, alkoxy, alkenyloxy or dialkylamino,R.sup.5 is alkyl or alkenyl, andR.sup.6 is carboxy or esterified carboxy.
    Type: Grant
    Filed: June 4, 1982
    Date of Patent: January 31, 1984
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Ikuo Ueda, Masayuki Kato, Masanobu Nagano
  • Patent number: 4426382
    Abstract: Novel piperazinylquinazoline and homopiperazinylquinazoline compounds which have useful antihypertensive activity and their use including pharmaceutical compositions containing said derivatives as the active antihypertensive component thereof. Said compounds have the following formula. ##STR1## wherein m is 2 or 3 and R is as defined in the specification.
    Type: Grant
    Filed: February 11, 1981
    Date of Patent: January 17, 1984
    Assignee: Sankyo Company Limited
    Inventors: Yasunobu Sato, Hiroshi Fukumi, Hiroyuki Koike, Hiroshi Nishino
  • Patent number: 4377581
    Abstract: 2,4-Diaminoquinazolines of the formula ##STR1## wherein Y.sup.1 is hydrogen or chloro, Y.sup.2 is OR, Y.sup.3 is hydrogen or OR such than when Y.sup.1 is hydrogen, Y.sup.3 is OR and when Y.sup.1 is chloro, Y.sup.3 is hydrogen or OR, and the pharmaceutically acceptable salts thereof; R represents an alkyl group having from one to three carbon atoms;taken separately, R.sup.1 and R.sup.2 are each hydrogen, alkyl having from one to five carbon atoms, cycloalkyl having from three to eight carbon atoms, alkenyl or alkynyl each having from three to five carbon atoms or hydroxy substituted alkyl having from two to five carbon atoms, when taken together with the nitrogen atom to which they are attached R.sup.1 and R.sup.2 form a substituted or unsubstituted heterocyclic group optionally containing an atom of oxygen, sulfur or a second atom of nitrogen as a ring member; their use as antihypertensive agents, pharmaceutical compositions containing them and intermediates for their production.
    Type: Grant
    Filed: April 10, 1981
    Date of Patent: March 22, 1983
    Assignee: Pfizer Inc.
    Inventors: Hans-Jurgen E. Hess, Jasjit S. Bindra, Praful K. Shah
  • Patent number: 4377580
    Abstract: Quinazoline derivatives of the formulae: ##STR1## wherein A.sup.1 is ##STR2## A.sup.2 is ##STR3## R.sup.1 is hydrogen, carboxy or esterified carboxy, R.sub.a.sup.1 and R.sub.b.sup.1 are esterified carboxy,R.sup.2 and R.sup.3 are hydrogen, alkyl, halogen, nitro, amino, alkoxy, aryloxy, alkylthio, alkylpiperazinyl, acylamino or dialkylamino which may be substituted with hydroxy,R.sup.4 is hydrogen, alkyl, hydroxy, alkoxy, alkenyloxy, dialkylamino or 2,2-dialkoxycarbonylvinylaminoR.sub.a.sup.4 is hydrogen, alkyl, hydroxy, alkoxy, alkenyloxy or dialkylamino,R.sup.5 is alkyl or alkenyl, andR.sup.6 is carboxy or esterified carboxy.
    Type: Grant
    Filed: November 25, 1980
    Date of Patent: March 22, 1983
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Ikuo Ueda, Masayuki Kato, Masanobu Nagano
  • Patent number: 4376858
    Abstract: 2,4-Diamino-5-methyl-6-[(3,4,5-trimethoxyanilino)methyl]quinazoline salts, pharmaceutical compositions containing said salts, methods of treating malaria, and bacterial infections employing said salts and compositions and methods for producing said salts.
    Type: Grant
    Filed: January 29, 1982
    Date of Patent: March 15, 1983
    Assignee: Warner Lambert Company
    Inventor: Norman L. Colbry
  • Patent number: 4351832
    Abstract: Herein is disclosed 2-(1-piperazinyl)-4-pyrimidinamine derivatives, acid addition salts thereof, processes for their preparation, methods of using the derivatives and pharmaceutical compositions of the derivatives. The derivatives are distinguished most readily by having novel substituents at position 4 of the piperazinyl radical, the substituents being selected from the group consisting of 2-thiazoylyl, oxazolo(4,5-b)pyridin-2-yl and optionally substituted 1-(lower alkyl)-1H-benzimidazol-2-yl. The derivatives are useful for treating hypertension in a mammal.
    Type: Grant
    Filed: March 20, 1981
    Date of Patent: September 28, 1982
    Assignee: American Home Products Corporation
    Inventors: Sumanas Rakhit, Jehan F. Bagli
  • Patent number: 4341893
    Abstract: Quinazoline derivatives of the formula (I): ##STR1## R=phenyl which is optionally substituted, furyl, thienyl or 5-alkylthio-1,3,4-oxadiazol-2-yl. These derivatives are useful as drugs, e.g. anti-hypertensive agents.
    Type: Grant
    Filed: May 9, 1977
    Date of Patent: July 27, 1982
    Assignee: Synthelabo
    Inventor: Philippe M. J. Manoury
  • Patent number: 4333937
    Abstract: Herein is disclosed 2-(1-piperazinyl)-4-pyrimidinamine derivatives, acid addition salts thereof, processes for their preparation, methods of using the derivatives and pharmaceutical compositions of the derivatives. The derivatives are distinguished most readily by having novel substituents at position 4 of the piperazinyl radical, the substituents being selected from the group consisting of optionally substituted 2-cycloheptimidazolyl, 1,4,5,6,7,8-hexahydrocycloheptimidazol-2-yl, 2-benzoxazolyl, benzthiazol-2-yl, 1H-2-benzimidazolyl and 1-oxo-2,4,6-cycloheptarien-2-yl. The derivatives are useful for treating hypertension in a mammal.
    Type: Grant
    Filed: April 18, 1980
    Date of Patent: June 8, 1982
    Assignee: American Home Products Corp.
    Inventors: Sumanas Rakhit, Jehan F. Bagli
  • Patent number: 4315007
    Abstract: Alkylenediamine amides corresponding to the general formula (I) ##STR1## in which R.sub.1 and R.sub.2 each represent, independently of one another, a hydrogen atom, an alkyl having 1 to 4 carbon atoms or the benzyl radical, n is equal to 2, 3 or 4 and R represents either a cycloalkyl radical having 3 to 6 carbon atoms, or a radical ##STR2## in which m is 0, 1 or 2, ##STR3## in which m is 0, 1 or 2 and p is 0, 1 or 2, and also their addition salts with pharmaceutically acceptable acids. These compounds may be prepared by reacting an aminoamide ##STR4## with a 4-amino-2-halogeno-6,7-dimethoxyquinazoline (II). The compounds are useful in treating cardiovascular disorders, and pharmaceutical compositions containing the compounds are also claimed.
    Type: Grant
    Filed: December 10, 1979
    Date of Patent: February 9, 1982
    Assignee: Synthelabo
    Inventor: Philippe M. Manoury
  • Patent number: 4309541
    Abstract: N-[1-(4-amino-2-quinazolinyl)-3 or 4-piperidinyl]-lactams, e.g., those of the formula ##STR1## and salts thereof are antihypertensive agents.
    Type: Grant
    Filed: April 9, 1980
    Date of Patent: January 5, 1982
    Assignee: Ciba-Geigy Corporation
    Inventor: Lincoln H. Werner
  • Patent number: 4287341
    Abstract: 2,4-Diaminoquinazolines of the formula ##STR1## wherein Y.sup.1 is hydrogen or chloro, Y.sup.2 is OR, Y.sup.3 is hydrogen or OR such that when Y.sup.1 is hydrogen, Y.sup.3 is OR and when Y.sup.1 is chloro, Y.sup.3 is hydrogen or OR, and the pharmaceutically acceptable salts thereof; R represents an alkyl group having from one to three carbon atoms;taken separately, R.sup.1 and R.sup.2 are each hydrogen, alkyl having from one to five carbon atoms, cycloalkyl having from three to eight carbon atoms, alkenyl or alkynyl each having from three to five carbon atoms or hydroxy substituted alkyl having from two to five carbon atoms, when taken together with the nitrogen atom to which they are attached R.sup.1 and R.sup.2 form a substituted or unsubstituted heterocyclic group optionally containing an atom of oxygen, sulfur or a second atom of nitrogen as a ring member; their use as antihypertensive agents, pharmaceutical compositions containing them and intermediates for their production.
    Type: Grant
    Filed: March 3, 1980
    Date of Patent: September 1, 1981
    Assignee: Pfizer Inc.
    Inventors: Hans-Jurgen E. Hess, Jasjit S. Bindra, Praful K. Shah
  • Patent number: 4279910
    Abstract: A series of novel 4-amino-6,7-di(lower alkoxy)-2-(4-substituted piperazino)quinazoline derivatives have been prepared, including their pharmaceutically acceptable acid addition salts. These derivatives all possess a benzo-oxacycloalkanoyl moiety located at the 4-position of the piperazine ring. Such compounds are useful in therapy as highly potent antihypertensive agents. 4-Amino-2-[4-(chroman-2-carbonyl)piperazino]-6,7-dimethoxyquinazoline represents a typical and preferred member compound. Methods for preparing all these compounds from known starting materials are provided and the principal synthetic route leading to the desired final products is described in some detail.
    Type: Grant
    Filed: April 15, 1980
    Date of Patent: July 21, 1981
    Assignee: Pfizer Inc.
    Inventor: Simon F. Campbell
  • Patent number: 4271300
    Abstract: An improved method is disclosed for producing antihypertensively active 6,7-dimethoxy-4-amino-2-[4-(2-furoyl)-1-piperazinyl] quinazoline hydrochloride, viz prazosine hydrochloride, by reacting methyl-N-(3,4-dimethoxy-6-cyano-phenyl)-[4-(2-furoyl)-1-piperazinyl]thiofo rmamidate with a large excess of ammonium chloride.
    Type: Grant
    Filed: January 9, 1980
    Date of Patent: June 2, 1981
    Assignee: Orion-yhtyma Oy
    Inventors: Erkki J. Honkanen, Aino K. Pippuri, Pekka J. Kairisalo, Heinrich Thaler, Maija K. Koivisto, Sirpa A. Tuomi
  • Patent number: 4256748
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1,R.sup.2,R.sup.3 and R.sup.4 are as hereinafter described, tautomers and salts thereof, are disclosed. The foregoing compounds inhibit the aggregation of blood platelets which renders them useful as therapeutic agents in the prophylaxis of thromboses. Furthermore, they are useful for the treatment and prophylaxis of cardiac insufficiency and cardiac failure, due to their inotropic activity without substantial tachycardia.
    Type: Grant
    Filed: June 20, 1979
    Date of Patent: March 17, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Madhukar S. Chodnekar, Ado Kaiser
  • Patent number: 4255429
    Abstract: N-[1-(4-amino-2-quinazolinyl)-3- or 4-piperidinyl]-lactams, e.g., those of the formula ##STR1## and salts thereof are antihypertensive agents.
    Type: Grant
    Filed: January 28, 1980
    Date of Patent: March 10, 1981
    Assignee: Ciba-Geigy Corporation
    Inventor: Lincoln H. Werner
  • Patent number: 4251532
    Abstract: An improved anti-hypertensive agent, the hydrochloride salt of 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-tetrahydrofuroyl)piperazine dihydrate.
    Type: Grant
    Filed: September 24, 1979
    Date of Patent: February 17, 1981
    Assignee: Abbott Laboratories
    Inventor: Robert Roteman
  • Patent number: 4243666
    Abstract: Regulators of the cardiovascular system and, in particular, in the treatment of hypertension having the formula ##STR1## wherein R is lower alkyl;X, is a 3- or 4-position substituent and is --(CH.sub.2).sub.n CONR.sup.1 R.sup.2, --O(CH.sub.2).sub.n CONR.sup.1 R.sup.2 or ##STR2## wherein n is 0, 1 or 2;R.sup.1 is hydrogen or lower alkyl, andR.sup.2 is lower alkyl; lower alkenyl, lower alkynyl, phenyl, substituted phenyl, C.sub.3 -C.sub.7 cycloalkyl; lower alkyl substituted by phenyl, substituted phenyl, C.sub.3 -C.sub.7 cycloalkyl, halogen, trifluoromethyl, hydroxy, lower alkoxy, lower alkoxycarbonyl, phenoxy, substituted phenoxy or --NR.sup.3 R.sup.4 wherein R.sup.3 and R.sup.4 each represent hydrogen, lower alkyl, lower alkanoyl or lower alkylsulfonyl; with the proviso that any O, N or halogen atom in R.sup.2 is separated by at least 2 carbon atoms from the nitrogen atom to which R.sup.2 is attached; orR.sup.1 and R.sup.
    Type: Grant
    Filed: May 14, 1979
    Date of Patent: January 6, 1981
    Assignee: Pfizer Inc.
    Inventors: Simon F. Campbell, John C. Danilewicz, Colin W. Greengrass, Rhona M. Plews
  • Patent number: 4237138
    Abstract: Regulators of the cardiovascular system and, in particular, in the treatment of hypertension having the formula ##STR1## pharmaceutically-acceptable bioprecursors thereof, and the pharmaceutically-acceptable acid addition salts thereof; wherein each of R.sup.1 and R.sup.2 is C.sub.1-4 alkyl or --CH.sub.2 CF.sub.3 ; alk is ethylene, monophenyl substituted ethylene, mono- and dimethyl substituted ethylene or monophenylmonomethyl substituted ethylene; and R.sup.3 is hydrogen, C.sub.1-4 alkyl, C.sub.3 -C.sub.6 cycloalkyl; phenyl or substituted phenyl; and methods for their preparation.
    Type: Grant
    Filed: April 16, 1979
    Date of Patent: December 2, 1980
    Assignee: Pfizer Inc.
    Inventors: Simon F. Campbell, John C. Danilewicz, Colin W. Greengrass
  • Patent number: 4230706
    Abstract: Quinazoline compounds of the formula: ##STR1## wherein A is ##STR2## wherein n is an integer of 1 or 2, or ##STR3## wherein X is O or CH.sub.2, and n and m are independently an integer of 1 or 2, and its non-toxic pharmaceutically acceptable salts, having an excellent antihypertensive activity without causing adverse effects such as orthostatic hypotension.
    Type: Grant
    Filed: March 19, 1979
    Date of Patent: October 28, 1980
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Isamu Maruyama, Shunji Aono, Junki Katsube
  • Patent number: 4188390
    Abstract: Compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof wherein R represents 6,7-di(lower alkoxy) or 6,7,8-tri(lower alkoxy);m is 1 or 2,X is --CHR.sup.1 -- or --CH.sub.2 CH.sub.2 --;each R.sup.1 and R.sup.0 may be the same or different and is hydrogen or lower alkyl;each of R.sup.2 and R.sup.3 is hydrogen, lower alkoxy, lower alkyl, halogen, lower alkanoyl, lower alkoxycarbonyl, --CONR.sup.4 R.sup.5 or --SO.sub.2 NR.sup.4 R.sup.5 wherein each of R.sup.4 and R.sup.5 is hydrogen or lower alkyl;processes for their preparation; and their use as regulators of the cardiovascular system, and particularly in the treatment of hypertension.
    Type: Grant
    Filed: October 18, 1978
    Date of Patent: February 12, 1980
    Assignee: Pfizer Inc.
    Inventor: Simon F. Campbell
  • Patent number: 4138561
    Abstract: Novel cyanocarboxamidines are disclosed. The new cyanocarboxamidines are particularly valuable as intermediates in the preparation of antihypertensive 4-amino-2-(4-substituted-piperazin-1-yl)-quinazolines.
    Type: Grant
    Filed: September 30, 1977
    Date of Patent: February 6, 1979
    Assignee: Bristol-Myers Company
    Inventors: Ronnie R. Crenshaw, George M. Luke, Richard A. Partyka
  • Patent number: 4128643
    Abstract: (2-Amino-4-quinazolinyl)-quanidines of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and n have the defined meanings, and their physiologically tolerable acid addition salts, process for preparing these compounds, pharmaceutical preparations containing them and their use as medicines.
    Type: Grant
    Filed: May 26, 1977
    Date of Patent: December 5, 1978
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wulf Merkel, Hans G. Alpermann, Karl Geisen, Norbert Kothe, Walter Ried
  • Patent number: 4101548
    Abstract: A series of novel 4-amino-2-(thiadiazole-carbonyl piperazinyl)-6,7-dimethoxyquinazolines is disclosed having antihypertensive properties. The thiadiazole substituent may be optionally substituted with alkyl or lower alkoxy carbonylamino groups. A representative embodiment of the invention is 4-amino-6,7-dimethoxy-2-[4-(5-ethoxy-carbonylamino-1,2,3-thiadiazole-4-car bonyl)-piperazin-1-yl]-quinazoline.
    Type: Grant
    Filed: February 22, 1977
    Date of Patent: July 18, 1978
    Assignee: Bristol-Myers Company
    Inventors: Ronnie R. Crenshaw, Richard A. Partyka
  • Patent number: 4092315
    Abstract: The invention relates to novel and valuable crystalline forms of the hypotensive agent prazosin hydrochloride. The anhydrous .alpha.-form is preferred because it is relatively non-hygroscopic and hence possesses important advantages in handling and formulation. The polyhydrate form of prazosin hydrochloride is preferred because of its low, uniform rate of dissolution.
    Type: Grant
    Filed: March 1, 1976
    Date of Patent: May 30, 1978
    Assignee: Pfizer Inc.
    Inventor: Ernest J. Bianco