Patents Assigned to Delmar Chemicals
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Patent number: 10745373Abstract: 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: GrantFiled: July 31, 2019Date of Patent: August 18, 2020Assignee: Delmar Chemicals Inc.Inventors: Nicolas Tesson, Eduard Bugan, Nadejda Spassova, Alain Menard
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Publication number: 20200039949Abstract: 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: ApplicationFiled: July 31, 2019Publication date: February 6, 2020Applicant: Delmar Chemicals Inc.Inventors: Nicholas Tesson, Eduard Bugan, Nadejda Spassova
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Patent number: 6512140Abstract: 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: GrantFiled: April 15, 2002Date of Patent: January 28, 2003Assignee: Delmar Chemicals Inc.Inventors: Lu Wei Liu, Yuan Wang, Hérika Marrugo, Sylvain Harper, David D. C. Quan, Zhihong (Nancy) Zhou, Gregory Bydlinski
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Patent number: 5942625Abstract: 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: GrantFiled: November 6, 1998Date of Patent: August 24, 1999Assignee: Delmar ChemicalsInventors: Yuan Wang, Lu Wei Liu, Alexandre L'Heureux, Olivier Lepage, Diane Phelan
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Patent number: 5068405Abstract: 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: GrantFiled: July 6, 1990Date of Patent: November 26, 1991Assignee: Delmar Chemicals Inc.Inventors: Michel Bekhazi, Josef Oren
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Patent number: 4200759Abstract: 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: GrantFiled: July 20, 1978Date of Patent: April 29, 1980Assignee: Delmar Chemicals, LimitedInventor: Robert A. Dickinson
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Patent number: 4153789Abstract: 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: GrantFiled: March 20, 1978Date of Patent: May 8, 1979Assignee: Delmar Chemicals LimitedInventors: Rudolf Kubela, Vaclav Musil, Lise A. Hughes
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Patent number: 4146629Abstract: 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: GrantFiled: September 12, 1977Date of Patent: March 27, 1979Assignee: Delmar Chemicals LimitedInventors: Rudolph Kubela, Jose M. Donascimento
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Patent number: 4138494Abstract: 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: GrantFiled: November 15, 1976Date of Patent: February 6, 1979Assignee: Delmar Chemicals LimitedInventors: Rudolf Kubela, Vaclav Musil, Lise A. Hughes
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Patent number: 4080330Abstract: 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: GrantFiled: June 23, 1975Date of Patent: March 21, 1978Assignee: Delmar Chemicals LimitedInventors: Rudolf Kubela, Vaclav Musil, Lise A. Hughes
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Patent number: 4048314Abstract: 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: GrantFiled: December 17, 1974Date of Patent: September 13, 1977Assignee: Delmar Chemicals LimitedInventors: Rudolph Kubela, Jose Maria Do Nascimento
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Patent number: 4042722Abstract: 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: GrantFiled: November 11, 1974Date of Patent: August 16, 1977Assignee: Delmar Chemicals LimitedInventors: Gerald J. Dunne, John D. Harvey
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Patent number: 3980674Abstract: 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: GrantFiled: January 28, 1974Date of Patent: September 14, 1976Assignee: Delmar Chemicals LimitedInventors: Rudolf Kubela, Lise A. Hughes
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Patent number: 3966761Abstract: 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: GrantFiled: February 7, 1974Date of Patent: June 29, 1976Assignee: Delmar Chemicals LimitedInventors: Ctirad Podesva, William T. Scott
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Patent number: 3957776Abstract: 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: GrantFiled: February 28, 1973Date of Patent: May 18, 1976Assignee: Delmar Chemicals LimitedInventors: Ctirad Podesva, Lise A. Hughes
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Patent number: 3957795Abstract: 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: GrantFiled: January 28, 1974Date of Patent: May 18, 1976Assignee: Delmar Chemicals LimitedInventors: Rudolf Kubela, Lise A. Hughes
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Patent number: 3953448Abstract: 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: GrantFiled: December 7, 1972Date of Patent: April 27, 1976Assignee: Delmar Chemicals LimitedInventors: Ctirad Podesva, William T. Scott, David W. Henson