Patents Assigned to Delmar Chemicals
  • Patent number: 10745373
    Abstract: The present invention relates to a process for preparing fluorescein quinoid form of Formula (I): Furthermore, the present invention relates to a new solid fluorescein form and a process for the preparation thereof. The present invention also relates to the use of said new solid fluorescein form in the synthesis of fluorescein quinoid form.
    Type: Grant
    Filed: July 31, 2019
    Date of Patent: August 18, 2020
    Assignee: Delmar Chemicals Inc.
    Inventors: Nicolas Tesson, Eduard Bugan, Nadejda Spassova, Alain Menard
  • Publication number: 20200039949
    Abstract: The present invention relates to a process for preparing fluorescein quinoid form of Formula (I): Furthermore, the present invention relates to a new solid fluorescein form and a process for the preparation thereof. The present invention also relates to the use of said new solid fluorescein form in the synthesis of fluorescein quinoid form.
    Type: Application
    Filed: July 31, 2019
    Publication date: February 6, 2020
    Applicant: Delmar Chemicals Inc.
    Inventors: Nicholas Tesson, Eduard Bugan, Nadejda Spassova
  • Patent number: 6512140
    Abstract: A process for the preparation of highly pure 1-(mercaptomethyl)-cyclopropaneacetic acid is described. Treatment of 1-(hydroxymethyl)-cyclopropaneacetonitrile with an acid provides the corresponding imino ester and/or halo-amide, which when reacted with thiourea provide the corresponding amide-isothiuronium salt. Hydrolysis of the amide-isothiuronium salt followed by an in situ oxidation allows the facile isolation and purification of 1-[1 -(carboxymethyl)-cyclopropanemethyldisulfanylmethyl]-cyclopropaneacetic acid (also known as 1-(mercaptomethyl)-cyclopropaneacetic acid disulfide). Reduction of the 1-(mercaptomethyl)-cyclopropaneacetic acid disulfide under mild conditions provides the 1-(mercaptomethyl)-cyclopropaneacetic acid with high purity.
    Type: Grant
    Filed: April 15, 2002
    Date of Patent: January 28, 2003
    Assignee: Delmar Chemicals Inc.
    Inventors: Lu Wei Liu, Yuan Wang, Hérika Marrugo, Sylvain Harper, David D. C. Quan, Zhihong (Nancy) Zhou, Gregory Bydlinski
  • Patent number: 5942625
    Abstract: Chloromethylpyridine hydrochlorides such as 3-chloromethylpyridine hydrochloride, an important pharmaceutical intermediate, are prepared in high yield and high purity by reacting the corresponding pyridyl carbinol with a slight excess of thionyl chloride, in solution in an inert solvent such as toluene. The pyridyl carbinol solution is added to the thionyl chloride gradually and under its surface, to prevent the formation of impurities. The product is recovered by applying vacuum or nitrogen purge to the reaction mixture to assist precipitation, followed by filtration and washing.
    Type: Grant
    Filed: November 6, 1998
    Date of Patent: August 24, 1999
    Assignee: Delmar Chemicals
    Inventors: Yuan Wang, Lu Wei Liu, Alexandre L'Heureux, Olivier Lepage, Diane Phelan
  • Patent number: 5068405
    Abstract: Halogenated N-sulfamyl propionamidine addition salts corresponding to the formula ##STR1## are provided, in which X represents halogen and A represents an acid selected from sulfuric acid, nitric acid, benzenesulfonic acid; toluenesulfonic acid; 2,4,5-trichlorobenzenesulfonic acid; trichloroacetic acid; trifluoroacetic acid or methanesulfonic acid. They are useful as intermediates in the preparation of famotidine. They are prepared by reacting a halogenated propionitrile with the respective acid.
    Type: Grant
    Filed: July 6, 1990
    Date of Patent: November 26, 1991
    Assignee: Delmar Chemicals Inc.
    Inventors: Michel Bekhazi, Josef Oren
  • Patent number: 4200759
    Abstract: The present invention relates to a process for the preparation of certain known imidazo[2,1-a]isoindoles of the general formula I: ##STR1## wherein X represents a hydrogen atom, a halogen atom or a lower alkoxy group. The said isoindoles, which may be prepared from novel lactams, have been shown to have utility as psychic energizers and anorectics.
    Type: Grant
    Filed: July 20, 1978
    Date of Patent: April 29, 1980
    Assignee: Delmar Chemicals, Limited
    Inventor: Robert A. Dickinson
  • Patent number: 4153789
    Abstract: The present invention is concerned with novel 2-unsubstituted-3-phenylindolines acid addition salts thereof. These compounds have been found to have valuable pharmacological properties indicative of possible utility, inter alia, of controlling coagulation of the blood and as hypoglycemic agents. The invention also provides novel processes for producing the novel compounds and pharmaceutical compositions containing same as active ingredients.
    Type: Grant
    Filed: March 20, 1978
    Date of Patent: May 8, 1979
    Assignee: Delmar Chemicals Limited
    Inventors: Rudolf Kubela, Vaclav Musil, Lise A. Hughes
  • Patent number: 4146629
    Abstract: The present invention is concerned with novel 4-aryl-3/4-amino/hydroxy-piperidine derivatives of the general formula I: ##STR1## wherein R.sub.1 represents hydrogen; lower alkyl; lower aralkyl; lower acyl; aminoalkyl, wherein the alkyl moiety contains 2 to 6 carbon atoms and the amino moiety may be mono- or dialkyl substituted --(CH.sub.2).sub.n --COOH; --(CH.sub.2).sub.n --OH; ##STR2## wherein X is hydrogen or halogen and n is 1, 2, 3 or 4; one of R.sub.2 and R.sub.3 represents a cyano, or a free amino group or a derivative thereof and the other represents a free or protected hydroxyl group; or R.sub.2 represents an azido group when R.sub.3 represents a free or protected hydroxyl group, or R .sub.2 and R.sub.3 together with their associated ring carbons represent an oxazepine ring, and Ar represents an aryl group which may be substituted by lower alkyl, lower alkoxy, halogen or CF.sub.3 , as well as addition salts thereof with organic or inorganic acids.
    Type: Grant
    Filed: September 12, 1977
    Date of Patent: March 27, 1979
    Assignee: Delmar Chemicals Limited
    Inventors: Rudolph Kubela, Jose M. Donascimento
  • Patent number: 4138494
    Abstract: The present invention is concerned with novel 2-unsubstituted-3-phenylindolines and acid addition salts thereof. These compounds have been found to have a valuable pharmacological property indicative of possible utility in controlling coagulation of the blood.
    Type: Grant
    Filed: November 15, 1976
    Date of Patent: February 6, 1979
    Assignee: Delmar Chemicals Limited
    Inventors: Rudolf Kubela, Vaclav Musil, Lise A. Hughes
  • Patent number: 4080330
    Abstract: The present invention is concerned with novel 2-unsubstituted-3-phenylindolines and acid addition salts thereof. These compounds have been found to have valuable pharmacological properties indicative of possible utility, inter alia, of controlling coagulation of the blood and as hypoglycemic agents. The invention also provides novel processes for producing the novel compounds and pharmaceutical compositions containing same as active ingredients.
    Type: Grant
    Filed: June 23, 1975
    Date of Patent: March 21, 1978
    Assignee: Delmar Chemicals Limited
    Inventors: Rudolf Kubela, Vaclav Musil, Lise A. Hughes
  • Patent number: 4048314
    Abstract: The present invention is concerned with novel 4-aryl-3/4-amino/hydroxy-piperidine derivatives of the general formula I: ##STR1## wherein R.sub.1 represents hydrogen; lower alkyl; lower aralkyl; lower acyl; aminoalkyl, wherein the alkyl moiety contains 2 to 6 carbon atoms and the amino moiety may be mono- or dialkyl substituted --(CH.sub.2).sub.n --COOH; --(CH.sub.2).sub.n --OH; ##STR2## wherein X is hydrogen or halogen and n is 1, 2, 3 or 4; one of R.sub.2 and R.sub.3 represents a cyano, or a free amino group or a derivative thereof and the other represents a free or protected hydroxyl group; or R.sub.2 represents an azido group when R.sub.3 represents a free or protected hydroxyl group, or R.sub.2 and R.sub.3 together with their associated ring carbons represent an oxazepine ring, and Ar represents an aryl group which may be substituted by lower alkyl, lower alkoxy, halogen or CF.sub.3, as well as addition salts thereof with organic or inorganic acids.
    Type: Grant
    Filed: December 17, 1974
    Date of Patent: September 13, 1977
    Assignee: Delmar Chemicals Limited
    Inventors: Rudolph Kubela, Jose Maria Do Nascimento
  • Patent number: 4042722
    Abstract: The present invention provides novel selenium containing additives for use as supplements in livestock feeds and processes for producing same. The novel supplements of the present invention use starch, especially wheat starch, as a carrier for the selenium-containing component and are remarkably homogeneous as regards distribution of the selenium content.
    Type: Grant
    Filed: November 11, 1974
    Date of Patent: August 16, 1977
    Assignee: Delmar Chemicals Limited
    Inventors: Gerald J. Dunne, John D. Harvey
  • Patent number: 3980674
    Abstract: The present invention is concerned with novel 7-oxabicyclo-[2.2.1]-5-heptene derivatives and a process for their production. These compounds are useful intermediates in the production of various pharmacologically active compounds.
    Type: Grant
    Filed: January 28, 1974
    Date of Patent: September 14, 1976
    Assignee: Delmar Chemicals Limited
    Inventors: Rudolf Kubela, Lise A. Hughes
  • Patent number: 3966761
    Abstract: This invention provides novel tertiary aminoindazole compounds of the following general formula: ##SPC1##Wherein R represents a hydrogen or halogen atom; R.sub.1 represents an alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted aralkyl group; R.sub.2 and R.sub.3 both represent a lower alkyl or aralkyl group and W represents a branched chain alkylene group, and salts, especially acid addition and quaternary ammonium salts thereof, and processes for making them. Such compounds are pharmacologically active in that they exhibit antiinflammatory and analgesic effects so the invention also provides pharmaceutical compositions containing one or more of these compounds as the active ingredient. They are also useful anti-microbial agents.
    Type: Grant
    Filed: February 7, 1974
    Date of Patent: June 29, 1976
    Assignee: Delmar Chemicals Limited
    Inventors: Ctirad Podesva, William T. Scott
  • Patent number: 3957776
    Abstract: Certain 2-substituted-4-substituted-1(2H)-phthalazinone compounds have hypotensive activity. Such compounds are used in pharmaceutical compositions. Processes of preparing them and the intermediate compounds are disclosed.
    Type: Grant
    Filed: February 28, 1973
    Date of Patent: May 18, 1976
    Assignee: Delmar Chemicals Limited
    Inventors: Ctirad Podesva, Lise A. Hughes
  • Patent number: 3957795
    Abstract: The present invention is concerned with novel cyclopentene and cyclopentane derivatives which have pharmacological, particularly analgesic and antiinflammatory activity, and are also useful intermediates in the preparation of other pharmacologically active compounds.
    Type: Grant
    Filed: January 28, 1974
    Date of Patent: May 18, 1976
    Assignee: Delmar Chemicals Limited
    Inventors: Rudolf Kubela, Lise A. Hughes
  • Patent number: 3953448
    Abstract: Novel 1,4-disubstituted piperazine compounds and pharmaceutical compositions incorporating such compounds in conjunction with orally, parenterally or rectally administrable pharmaceutically acceptable carriers are disclosed. These compounds have coronary vasodilating properties. Also disclosed are processes for preparing these compounds, and novel intermediate compounds used in such processes.
    Type: Grant
    Filed: December 7, 1972
    Date of Patent: April 27, 1976
    Assignee: Delmar Chemicals Limited
    Inventors: Ctirad Podesva, William T. Scott, David W. Henson