1,2,4-benzothiadiazines Patents (Class 544/12)
  • Patent number: 4889851
    Abstract: A compound of the formula: ##STR1## wherein R' is phenyl, phenyl which is substituted with halogen, lower alkyl, lower alkoxy, halo lower alkyl, lower alkylamino, lower alkylthio, phenoxy, carboxy, lower alkoxycarbonyl, carboxy lower alkyl, lower alkoxycarbonyl, lower alkyl, cyclo lower alkyl; lower alkyl which is substituted with carboxy or lower alkoxyoxycarbonyl; or pyrimidinyl, pyridyl or pyridyl which is substituted with lower alkyl;A is lower alkylene;n is an integer of 0 or 1;R.sup.2 is lower alkyl;R.sup.3 is hydrogen; hydroxy; halogen; halo lower alkyl; lower alkyl; lower alkylamino; lower alkanoyl amino; lower alkanoyl lower alkylamino; lower alkoxy; lower alkoxy which is substituted with phenyl, phthalimido, pyranyl, amino, carboxy, lower alkoxycarbonyl, cyclo lower alkyl or cyclo lower alkyl which is substituted with amino lower alkyl or lower alkoxycarbonylamino lower alkyl; or cyclo lower alkyloxy or cyclo lower alkyloxy which is substituted with carboxy or lower alkoxycarbonyl;R.sup.
    Type: Grant
    Filed: November 5, 1987
    Date of Patent: December 26, 1989
    Assignee: Fujisawa Pharmaceutical Co, Ltd.
    Inventors: Teruo Oku, Eishiro Todo, Chiyoshi Kasahara, Katsuya Nakamura, Hiroshi Kayakiri
  • Patent number: 4883800
    Abstract: The invention relates to compounds having aldose reductase-inhibitory activity of the formula: ##STR1## in which R.sup.1 and R.sup.2 are each hydrogen, halogen, lower alkoxy or halo(lower)alkyl,R.sup.3 is phenyl(lower)alkyl which may have one or more substituent(s) selected from the group consisting of halogen, lower alkoxy, halo(lower)alkyl and lower alkyl,R.sup.4 is carboxy or protected carboxy,A is sulfur atom,Y is carbonyl, thiocarbonyl or sulfonyl andZ is lower alkylene,and pharmaceutically acceptable salts thereof, useful in treating diabetic complications.
    Type: Grant
    Filed: December 8, 1987
    Date of Patent: November 28, 1989
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Masashi Hashimoto, Teruo Oku, Yoshikuni Ito, Takayuki Namiki, Kozo Sawada, Chiyoshi Kasahara, Yukihisa Baba
  • Patent number: 4818756
    Abstract: The invention relates to substituted 2-pyrimidinyl-1-piperazine derivatives defined herein by formula (I), processes for their manufacture, compositions containing said substituted 2-pyrimidinyl-1-piperazine derivatives as active materials and the use of said compounds and compositions as agents effecting the central nervous system. Also included in the invention are intermediates of formula (VIII) for making the active formula (I) compounds.
    Type: Grant
    Filed: March 10, 1986
    Date of Patent: April 4, 1989
    Assignee: Troponwerke GmbH & Co., KG
    Inventors: Peter-Rudolf Seidel, Harald Horstmann, Jorg Traber, Wolfgang Dompert, Thomas Glaser, Teunis Schuurman
  • Patent number: 4749698
    Abstract: Compounds having the general structure ##STR1## and their pharmaceutically acceptable salts, wherein the substituents are defined herein, which exhibit antihypertensive activity.
    Type: Grant
    Filed: July 8, 1985
    Date of Patent: June 7, 1988
    Assignee: Rorer Pharmaceutical Corporation
    Inventors: Edward S. Neiss, John T. Suh, John R. Regan, Jerry W. Skiles, Jeffrey N. Barton, James J. Mencel, Paul Menard
  • Patent number: 4746676
    Abstract: Compounds having the general structure ##STR1## and their pharmaceutically acceptable salts, wherein the substituents are defined herein, which exhibit antihypertensive activity.
    Type: Grant
    Filed: September 12, 1984
    Date of Patent: May 24, 1988
    Assignee: Rorer Pharmaceutical Corporation
    Inventors: Edward S. Neiss, John T. Suh, John R. Regan, Jerry W. Skiles, Jeffrey N. Barton, Paul Menard
  • Patent number: 4734419
    Abstract: The invention relates to compounds of the formula: ##STR1## in which R.sup.1 and R.sup.2 are each hydrogen, halogen, lower alkoxy or halo(lower)alkyl,R.sup.3 is dihalophenyl, naphthyl(lower)alkyl, phenyl(lower)alkyl substituted by one or two substituent(s) selected from the group consisting of halogen, lower alkoxy, halo(lower)alkyl and lower alkyl, or thienyl(lower)alkyl,R.sup.4 is carboxy or protected carboxy,Y is carbonyl, thiocarbonyl or sulfonyl andZ is lower alkylene, and pharmaceutically acceptable salts thereof, useful in the treatment of diabetic complications.
    Type: Grant
    Filed: September 16, 1986
    Date of Patent: March 29, 1988
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Masashi Hashimoto, Teruo Oku, Yoshikuni Ito, Takayuki Namiki, Kozo Sawada, Chiyoshi Kasahara, Yukihisa Baba
  • Patent number: 4716161
    Abstract: A phenylpiperazine derivative according to the present invention has the following general formula [I]: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are independently hydrogen or alkoxy group having 1 to 3 carbon atoms, orR.sup.1 and R.sup.2 or R.sup.2 and R.sup.3 together with carbon atoms to which they are attached form --O(CH.sub.2).sub.m O-- wherein m is an integer of 1 to 3, oreither R.sup.1 or R.sup.2 is amine residue selected from the group consisting of --NH.sub.2 , --NHSO.sub.2 CH.sub.3, --NHCOCH.sub.3 and --NHCONH.sub.2 and the other is hydrogen or alkoxy group of 1 to 3 carbon atoms and R.sup.3 is hydrogen;R.sup.4 and R.sup.5 are independently hydrogen or alkyl group of 1 to 3 carbon atoms;Y is --CO-- or --SO.sub.2 -- provided that at least one of R.sup.1 and R.sup.2 is not hydrogen when Y is --CO--; andn is an integer of 2 to 4.An acid addition salt of the phenylpiperazine derivative having the general formula [I] is included in the present invention.
    Type: Grant
    Filed: April 3, 1985
    Date of Patent: December 29, 1987
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Harukazu Fukami, Ryoji Kikumoto, Kenichiro Nakao, Issei Nitta, Shinya Inoue
  • Patent number: 4696939
    Abstract: Compounds of the formula ##STR1## and their pharmaceutically acceptable salts, wherein the substituents are as defined herein, having antihypertensive activity.
    Type: Grant
    Filed: November 29, 1985
    Date of Patent: September 29, 1987
    Assignee: USV Pharmaceutical Corporation
    Inventors: John T. Suh, John J. Piwinski, Howard Jones, Edward S. Neiss
  • Patent number: 4681886
    Abstract: This invention is directed to substituted 4-phenoxy and 4-phenylthio prolines of the formula ##STR1## which possess useful hypotensive activity.
    Type: Grant
    Filed: April 25, 1983
    Date of Patent: July 21, 1987
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Rudiger D. Haugwitz, Peter W. Sprague
  • Patent number: 4666906
    Abstract: Compounds of the formula ##STR1## and their pharmaceutically acceptable salts, wherein the substituents are as defined herein, having antihypertensive activity.
    Type: Grant
    Filed: July 19, 1985
    Date of Patent: May 19, 1987
    Assignee: USV Pharmaceutical Corporation
    Inventors: John J. Piwinski, John T. Suh, Paul Menard, Howard Jones, Edward S. Neiss, John R. Regan
  • Patent number: 4634779
    Abstract: There are described novel dyes of the formulae ##STR1## in which R.sub.1 and R.sub.2 independently of one another are each hydrogen, unsubstituted or substituted alkyl, cycloalkyl, aralkyl or aryl, and R.sub.1 and R.sub.2 together with the nitrogen atom, and optionally with the inclusion of further hetero atoms, can also form a 5- to 7-membered heterocycle, or one of the radicals R.sub.1 or R.sub.2 can be linked with the carbon atom, in the o-position with respect to the amino group, of the ring A to form a fused-on, saturated, unsubstituted or substituted 5- or 6-membered ring,X is .dbd.NR.sub.3, .dbd.NCOR.sub.4, ##STR2## .dbd.NH or .dbd.O, wherein R.sub.3 is alkyl or unsubstituted or substituted phenyl,R.sub.4 is unsubstituted or substituted alkyl, aralkyl, aryl, vinyl, alkoxy, phenoxy or amino, andR.sub.5 is cyano, carbalkoxy, or unsubstituted or substituted carbonamide, andR.sub.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: January 6, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Mockli
  • Patent number: 4609738
    Abstract: There are described novel dyes of the formulae ##STR1## in which R.sub.1 and R.sub.2 independently of one another are each hydrogen, unsubstituted or substituted alkyl, cycloalkyl, aralkyl or aryl, and R.sub.1 and R.sub.2 together with the nitrogen atom, and optionally with the inclusion of further hetero atoms, can also form a 5- to 7-membered heterocycle, or one of the radicals R.sub.1 or R.sub.2 can be linked with the carbon atom, in the o-position with respect to the amino group, of the ring A to form a fused-on, saturated, unsubstituted or substituted 5- or 6-membered ring,X is .dbd.NR.sub.3, .dbd.NCOR.sub.4, ##STR2## .dbd.NH or .dbd.O, wherein R.sub.3 is alkyl or unsubstituted or substituted phenyl,R.sub.4 is unsubstituted or substituted alkyl, aralkyl, aryl, vinyl, alkoxy, phenoxy or amino, andR.sub.5 is cyano, carbalkoxy, or unsubstituted or substituted carbonamide, andR.sub.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: September 2, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Mockli
  • Patent number: 4585793
    Abstract: Certain novel heterocyclic compounds, aromatic thioesters, their preparation, and their use in inhibiting serine proteases with chymotrypsin-like and elastase-like specificity and in the treatment of diseases such as emphysema which involve tissue proteolysis.
    Type: Grant
    Filed: May 9, 1983
    Date of Patent: April 29, 1986
    Assignee: Georgia Tech Research Institute
    Inventor: James C. Powers
  • Patent number: 4578459
    Abstract: Heterocyclic compounds which are inhibitors of histamine activity, in particular, inhibitors of H-2 histamine receptors. A specific compound of this invention is 2-[2-(4-methyl-5-imidazolylmethylthio)ethylamino]-4-pyrimidone.
    Type: Grant
    Filed: June 8, 1984
    Date of Patent: March 25, 1986
    Assignee: SmithKline & French Laboratories Limited
    Inventors: Graham J. Durant, John C. Emmett, Charon R. Ganellin
  • Patent number: 4576941
    Abstract: Compounds of the formula ##STR1## and their pharmaceutically acceptable salts, wherein the substituents are as defined herein, having antihypertensive activity.
    Type: Grant
    Filed: February 29, 1984
    Date of Patent: March 18, 1986
    Assignee: USV Pharmaceutical Corp.
    Inventors: John T. Suh, John J. Piwinski, Howard Jones, Edward S. Neiss
  • Patent number: 4558044
    Abstract: Disclosed are compounds of the formulaR.sub.1 --Ar--(CH.sub.2).sub.a --X--(CH.sub.2).sub.b --NH--Hetwherein R.sub.1 is guanidino or substituted guanidino, Ar is furandiyl, thiophendiyl, phenylene, pyridinediyl, pyrimidinediyl, thiazolediyl, thiadiazolediyl or imidazolediyl; a is 0, 1 or 2; b is 2, 3, 4 or 5; and Het is a bicyclic heteroary group, and pharmaceutically acceptable salts, quaternized derivatives, N-oxides and solvates thereof. The compounds are useful for the treatment or prophylaxis of disorders relating to excess gastric acid secretion in mammals.
    Type: Grant
    Filed: September 29, 1983
    Date of Patent: December 10, 1985
    Assignee: Beecham Group p.l.c.
    Inventor: Francis D. King
  • Patent number: 4550171
    Abstract: There are described novel dyes of the formulae ##STR1## in which R.sub.1 and R.sub.2 independently of one another are each hydrogen, unsubstituted or substituted alkyl, cycloalkyl, aralkyl or aryl, and R.sub.1 and R.sub.2 together with the nitrogen atom, and optionally with the inclusion of further hetero atoms, can also form a 5- to 7-membered heterocycle, or one of the radicals R.sub.1 or R.sub.2 can be linked with the carbon atom, in the o-position with respect to the amino group, of the ring A to form a fused-on, saturated, unsubstituted or substituted 5- or 6-membered ring,X is .dbd.NR.sub.3, .dbd.NCOR.sub.4, ##STR2## .dbd.NH or .dbd.O, wherein R.sub.3 is alkyl or unsubstituted or substituted phenyl,R.sub.4 is unsubstituted or substituted alkyl, aralkyl, aryl, vinyl, alkoxy, phenoxy or amino, andR.sub.5 is cyano, carbalkoxy, or unsubstituted or substituted carbonamide, andR.sub.
    Type: Grant
    Filed: October 10, 1978
    Date of Patent: October 29, 1985
    Assignee: Ciba Geigy Corporation
    Inventor: Peter Mockli
  • Patent number: 4547579
    Abstract: There are described novel dyes of the formulae ##STR1## in which R.sub.1 and R.sub.2 independently of one another are each hydrogen, unsubstituted or substituted alkyl, cycloalkyl, aralkyl or aryl, and R.sub.1 and R.sub.2 together with the nitrogen atom, and optionally with the inclusion of further hetero atoms, can also form a 5- to 7-membered heterocycle, or one of the radicals R.sub.1 or R.sub.2 can be linked with the carbon atoms, in the o-position with respect to the amino group, of the ring A to form a fused-on, saturated, unsubstituted or substituted 5- or 6- membered ring,X is .dbd.NR.sub.3, .dbd.NCOR.sub.4, ##STR2## .dbd.NH or .dbd.O, wherein R.sub.3 is alkyl or unsubstituted or substituted phenyl,R.sub.4 is unsubstituted or substituted alkyl, aralkyl, aryl, vinyl, alkoxy, phenoxy or amino, andR.sub.5 is cyano, carbalkoxy, or unsubstituted or substituted carbonamide, andR.sub.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: October 15, 1985
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Mockli
  • Patent number: 4536501
    Abstract: Compounds of the formula ##STR1## are disclosed. They possess angiotensin converting enzyme inhibition activity and diuretic activity and are therefore useful as antihypertensive agents.
    Type: Grant
    Filed: March 30, 1984
    Date of Patent: August 20, 1985
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Joseph E. Sundeen, Rudiger D. Haugwitz, Peter W. Sprague
  • Patent number: 4442094
    Abstract: Compounds of the formula Het--O--CH.sub.2 --CHOR--CH.sub.2 --NH-aralkyl where Het is a 10 membered N-containing ring are disclosed. The compounds are useful as pharmaceuticals.
    Type: Grant
    Filed: February 22, 1982
    Date of Patent: April 10, 1984
    Assignee: Merck & Co., Inc.
    Inventors: Joseph G. Atkinson, John J. Baldwin, David E. McClure
  • Patent number: 4349673
    Abstract: Compounds of the formula Het--O--CH.sub.2 --CHOR--CH.sub.2 -NHaralkyl where Het is a 10 membered N-containing ring are disclosed. The compounds are useful as pharmaceuticals.
    Type: Grant
    Filed: December 23, 1980
    Date of Patent: September 14, 1982
    Assignees: Merck & Co., Inc., Merck Sharp & Dohme Corp.
    Inventors: Joseph G. Atkinson, John J. Baldwin, David E. McClure
  • Patent number: 4338435
    Abstract: Compounds having the formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently hydrogen, halogen, trifluoromethyl, aminosulfonyl, nitro, alkyl or alkoxy;R.sub.3 is hydrogen, alkyl, or phenylmethyl;R.sub.4 is hydrogen, alkyl, or phenyl, and R.sub.15 is alkyl, phenyl or phenylmethyl, or R.sub.4 and R.sub.15 together are --(CH.sub.2).sub.m -- wherein m is 1 or 2;R.sub.5,R.sub.6,R.sub.7,R.sub.8,R.sub.9,R.sub.10,R.sub.11,R.sub.12,R.sub.13 and R.sub.14 are each independently hydrogen, halogen, alkyl or phenyl;n.sub.1,n.sub.2,n.sub.3,n.sub.4 and n.sub.5 are each independently 0 or 1;with the proviso that if R.sub.4 and R.sub.15 together are --(CH.sub.2).sub.m -- the sum of n.sub.1, n.sub.2, n.sub.3, n.sub.4, n.sub.5 and m is 2 or 3;have diuretic activity.
    Type: Grant
    Filed: June 1, 1981
    Date of Patent: July 6, 1982
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Rudiger D. Haugwitz
  • Patent number: 4260744
    Abstract: Heterocyclic compounds which are inhibitors of histamine activity, in particular, inhibitors of H-2 histamine receptors. A specific compound of this invention is 2-[2-(4-methyl-5-imidazolylmethylthio)ethylamino]-4-pyrimidone.
    Type: Grant
    Filed: January 30, 1979
    Date of Patent: April 7, 1981
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, John C. Emmett, Charon R. Ganellin
  • Patent number: 4184039
    Abstract: Novel Benzothiadiazines which stimulate hair growth when applied intraperitoneally, orally or topically.
    Type: Grant
    Filed: December 1, 1977
    Date of Patent: January 15, 1980
    Inventors: Gianluigi Soldati, David A. Schlichting, Paul Finkelstein
  • Patent number: 4171361
    Abstract: 1-Substituted-3-amino-6,7-dialkoxy-1H-1,2,4-benzothiadiazine-1-oxides, useful as hypotensive agents.
    Type: Grant
    Filed: March 31, 1977
    Date of Patent: October 16, 1979
    Assignee: Eli Lilly and Company
    Inventors: Robert D. Dillard, Donald E. Pavey
  • Patent number: 4104381
    Abstract: Heterocyclic compounds which are inhibitors of histamine activity, in particular, inhibitors of H-2 histamine receptors. A specific compound of this invention is 2-[2-(4-methyl-5-imidazolylmethylthio)ethylamino]-4-pyrimidone.
    Type: Grant
    Filed: October 29, 1976
    Date of Patent: August 1, 1978
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham John Durant, John Colin Emmett, Charon Robin Ganellin
  • Patent number: 4100280
    Abstract: 1,3-Dialkyl-6,7-methoxy-1H-1,2,4-benzothiadiazine-1-oxides, useful as hypotensive agents.
    Type: Grant
    Filed: August 8, 1977
    Date of Patent: July 11, 1978
    Assignee: Eli Lilly and Company
    Inventors: Robert D. Dillard, Donald E. Pavey
  • Patent number: 4041028
    Abstract: Novel 2,3-disubstituted-1,2,4-benzothiadiazine 1,1-dioxides of the formula: ##STR1## wherein X is hydrogen or chlorine. The novel compositions have been obtained by an unexpected side chain chlorination and have been found to be useful in medicinal chemistry as antihypertensives.
    Type: Grant
    Filed: April 24, 1975
    Date of Patent: August 9, 1977
    Assignee: Carter-Wallace, Inc.
    Inventor: Gianluigi Soldati