Patents Assigned to Gist-Brocades N.V.
-
Patent number: 4182870Abstract: An improved process for the preparation of 3-bromomethyl-3-cephem sulfoxide derivatives of the formula ##STR1## wherein R.sub.1 is an acylamido group and R.sub.2 is a group protecting the carboxy radical which are valuable intermediates for the preparation of various therapeutically useful cephalosporanic acid derivatives.Type: GrantFiled: August 30, 1978Date of Patent: January 8, 1980Assignee: Gist-Brocades N.V.Inventors: Cornelis A. Bruynes, Jan J. de Koning
-
Patent number: 4177189Abstract: An improved process for the preparation in high yields of a compound of the formula ##STR1## wherein R is an optionally substituted phenyl group, Y is selected from the group consisting of Me and a hydrocarbon, Me is a metal cation and E is selected from the group consisting of hydrogen and a metal cation comprising reacting a compound of the formula ##STR2## wherein Q is selected from the group consisting of hydrogen and a silyl protecting group, Rz is an optionally substituted phenyl with the proviso that any hydroxy group present on the phenyl are replaced by --OQz, wherein Qz is a silyl protecting group and Ez is a carboxyl protecting group, with a compound of the formula ##STR3## wherein Z is a halogen and X is selected from the group consisting of OY and Z at low temperatures under anhydrous conditions and carefully hydrolyzing the resulting product either with just enough water to remove protecting groups and hydrolyze the Z groups to hydroxy groups and, still under anhydrous conditions, reacting the cType: GrantFiled: May 22, 1978Date of Patent: December 4, 1979Assignee: Gist-Brocades N.V.Inventors: Piet J. Akkerboom, Geertruiida J. Lower, Willem J. Timp
-
Patent number: 4164446Abstract: Novel 18.xi.-, 19.xi.- and 20.xi.-hydroxy-prostaglandin derivatives of the formula I ##STR1## wherein the dotted line in the position 8-12 indicates the optional presence of a double bond, the waved lines in position 15 indicate that the hydroxyl group and the group R.sub.4 are either in .alpha.- or .beta.-position and Z represents a --CH.sub.2 CH.sub.2 -- or a cis --CH.dbd.CH--group, and wherein R represents one of the groups: ##STR2## (wherein the waved lines indicate that the hydroxyl groups are either in .alpha.- or .beta.-position and R.sub.1 represents a hydrogen atom, a methyl or ehtyl group), R.sub.2 represents either an oxygen atom or a hydrogen atom and an .alpha.- or .beta.-hydroxyl group, R.sub.3 represents a hydrogen atom or a hydroxyl group and R.sub.4 represents a hydrogen atom or a methyl group, with the proviso that when simultaneously, R.sub.1, R.sub.3 and R.sub.4 each represents a hydrogen atom, R.sub.Type: GrantFiled: September 9, 1977Date of Patent: August 14, 1979Assignee: Gist Brocades N.V.Inventors: Arthur F. Marx, Jean Doodewaard
-
Patent number: 4160829Abstract: 1,2,4-Oxadiazolylacetic acid derivatives. The derivatives include penicillin and cephalosporin amides which have antibiotic properties.Type: GrantFiled: May 9, 1977Date of Patent: July 10, 1979Assignee: Gist-Brocades N.V.Inventors: Robert Heijboer, Antoon VAN Harrewijn, Peter W. Henniger
-
Patent number: 4155813Abstract: Fermentation process, e.g. for the production of an oxidation product such as vinegar, which comprises continuously cultivating a bacterial strain, preferably in a vessel of elongated shape, in a medium containing the substrate to be fermented in the presence of a hydrous oxide of a metal selected from the group consisting of titanium, vanadium, zirconium, iron and tin and a chelated polyhydroxy support. The bacterial strain used in the process is preferably chelated or complexed with the hydrous metal oxide and the polyhydroxy support.Type: GrantFiled: February 14, 1977Date of Patent: May 22, 1979Assignee: Gist-Brocades N.V.Inventors: Sidney A. Barker, Roderick N. Greenshields, John D. Humphreys, John F. Kennedy
-
Patent number: 4152441Abstract: .alpha.,.alpha.-Diarylimidazole-2-methanols of the general formula ##STR1## wherein R.sub.1 -R.sub.10 are the same or different and each represents a hydrogen or halogen atom or a trifluoromethyl or tertiary butyl group, with at least one of said R.sub.1 -R.sub.10 being halogen, trifluoromethyl or tertiary butyl; R.sub.11 and R.sub.12 are the same or different and each represents a hydrogen atom, an alkyl group, a phenyl group or a halogen-or trifluoromethyl-substituted phenyl group; and R.sub.13 represents a hydrogen atom or a lower alkyl group, a lower alkoxymethyl group, a phenylalkyl group (optionally substituted in the phenyl moiety by one or more halogen atoms or alkyl or trifluoromethyl groups), an alkenyl group, a phenyl(lower)alkoxymethyl group (optionally substituted in the phenyl moiety by one or more halogen atoms or alkyl or trifluoromethyl groups) or a benzenesulfonyl group (in which the phenyl moiety is optionally substituted by one or more alkyl groups) are described.Type: GrantFiled: February 2, 1973Date of Patent: May 1, 1979Assignee: Gist-Brocades N.V.Inventors: Cornelis VAN DER Stelt, Petrus S. Hofman
-
Patent number: 4149535Abstract: A catheter holding device having longitudinally-extending walls defining an open-ended body with a main passage therethrough. At least a portion of the main passage is aligned with openings in forward and rear ends of the body. The portion of the walls adjacent the opening in the forward end of the body is adapted for receipt within a blood vessel or cavity. Another portion of the walls has a side opening allowing communication with the main passage. A side tube encompasses the side opening and extends from the body. Resilient material having a central passage therethrough is located within the side tube. The resilient material is designed to be compressed and grip a catheter which is passed through the material, into and through the main passage. A leading portion of the catheter projects beyond the forward end of the body. Clearance is left between at least one of the walls of the main passage and the catheter to allow simultaneous passage of liquids through both the main passage and the catheter.Type: GrantFiled: May 6, 1977Date of Patent: April 17, 1979Assignee: Gist-Brocades N.V.Inventor: Joy G. R. Volder
-
Patent number: 4148891Abstract: An antifungal preparation to be used in and on agricultural products such as fruit, vegetables, tubers, root-tubers, flower bulbs and rootstocks comprising an amount of polyene antibiotic, peferably natamycin, effective to prevent or inhibit mold growth on the agricultural products dissolved in a mixture of a lower alkanol, such as ethyl alcohol, and a lower alkanoic acid, such as acetic acid and agricultural products treated with this preparation and the method of treatment by submerging the agricultural products in the preparation or by pasting or spraying the preparation onto the agricultural products.Type: GrantFiled: March 6, 1978Date of Patent: April 10, 1979Assignee: Gist-Brocades N.V.Inventor: Dirk A. Smink
-
Patent number: 4132777Abstract: Antifungal compositions useful for the treatment of ringworm and other fungal infections comprising an antifungally effective amount of natamycin and a non-toxic, pharmaceutically acceptable organic acid compound and a suitable liquid carrier which compositions may be sprayed onto the animal, applied by a sponge or by other topical administration and concentrate comprising natamycin and the non-toxic, pharmaceutically acceptable organic acid compound in dry form.Type: GrantFiled: November 24, 1976Date of Patent: January 2, 1979Assignee: Gist-Brocades N.V.Inventors: Jan L. van Os, Engbert P. Oldenkamp, Dirk A. Smink
-
Patent number: 4130665Abstract: Therapeutically useful A-nor-androsta-3(5),16-dien-2-one derivatives of the general formula: ##STR1## wherein R.sub.1 and R.sub.2 each represent a hydrogen atom or a methyl group, process for their preparation by dehydrating in the 16-17 position a corresponding 17-hydroxy compound, and pharmaceutical compositions for the treatment of dermatological disorders, which comprise, as an active ingredient at least one of the A-nor-steroids as defined by formula I, are disclosed.Type: GrantFiled: March 28, 1978Date of Patent: December 19, 1978Assignee: Gist-Brocades N.V.Inventors: Arthur F. Marx, Cornelis Vos
-
Patent number: 4128547Abstract: A process for the preparation of 6-(D-.alpha.-amino-p-hydroxyphenylacetamido)-penicillanic acid or amoxicillin by reacting 6-aminopenicillanic acid with at least two equivalents of a silylating agent producing trimethylsilyl groups in an anhydrous, inert, water-insoluble organic solvent and reacting the resulting product at a temperature below -25.degree. C with an at least equimolar amount of a compound of the formula ##STR1## wherein R.sub.1 and R.sub.7 are lower alkoxy, R.sub.2 is lower alkyl and R.sub.3 is selected from the group consisting of lower alkyl and hydrogen previously prepared from the corresponding Dane salt and an acid chloride under anhydrous conditions in the presence of a tertiary amine in an inert, water-insoluble organic solvent.Type: GrantFiled: November 25, 1977Date of Patent: December 5, 1978Assignee: Gist-Brocades N.V.Inventors: Johannes K. van der Drift, Peter W. Henniger, Gerard J. VAN Veen
-
Patent number: 4075233Abstract: Therapeutically useful 16-dehydro-androstane derivatives of the general formula: ##STR1## processes for their preparation and pharmaceutical compositions for the treatment of dermatological disorders, which contain as active ingredient at least one of the 16-dehydro-androstane derivatives as defined by the above formula.Type: GrantFiled: July 15, 1976Date of Patent: February 21, 1978Assignee: Gist-Brocades N.V.Inventors: Arthur Friedrich Marx, Nicolaas Cornelis Maria Emanuel Barendse
-
Patent number: 4075337Abstract: R-sulfoxides of the formulae ##STR1## wherein ##STR2## represents an usual penicillin or cephalosporin amide group and X is selected from the group consisting of hydrogen, hydroxy, an alkanoyloxy and the residue of a nucleophilic agent and their salts and esters are prepared by oxidation of the corresponding penicillins and cephalosporins to convert the sulfur atom in the ring to a sulfoxide group and separating and isolating the penicillin- or cephalosporin R-sulfoxide so formed from the reaction mixture or by acylation of the free amino group of the intermediate 6-aminopenicillanic acid R-sulfoxide and 7-aminocephalosporanic acid R-sulfoxide and derivatives. A preferred straight oxidation method is the photosensitized oxygenation method.Type: GrantFiled: November 18, 1975Date of Patent: February 21, 1978Assignee: Gist-Brocades N.V.Inventors: Arthur Friedrich Marx, Jan Verwey, Peter Max Smid
-
Patent number: 4067986Abstract: Penicillanic acid derivatives of the formula ##STR1## wherein E is selected from the group consisting of hydrogen, a salt forming cation, and an ester forming residue which is known to improve the absorption characteristics of penicillanic compounds after oral administration to humans or animals, and Y is a group of the formula ##STR2## wherein Z.sub.1 and Z.sub.2 are individually selected from the group consisting of lower alkoxy, optionally substituted phenoxy, optionally substituted benzyl and benzyloxy group, optionally substituted lower alkyl, optionally substituted phenyl, hydroxy and -OM wherein M represents a salt forming cation, and hydrates of the said salts having antibacterial properties and their preparation and novel intermediates.Type: GrantFiled: October 20, 1975Date of Patent: January 10, 1978Assignee: Gist-Brocades N.V.Inventors: Cornelis Adrianus Bruynes, Johannes Karel Van der Drift
-
Patent number: 4062948Abstract: A new antibiotic (now called dihydromocimycin) being a yellow, salt-forming weak acid and its non-toxic, pharmaceutically acceptable salts produced by a novel microorganism called Streptomyces ramocissimus, a sample of which is deposited in the collection of "Centraal Bureau voor Schimmel-cultures" at Baarn, The Netherlands, under No. CBS 190.69, or mutants thereof, which antibiotic has antibacterial properties and has been found to be effective against Treponema dysentry, one of the most common swine diseases. Dihydromocimycin may also be converted into mocimycin which is an antibiotic which also possesses growth-promoting properties when added to animal feeds by a dehydrogenation reaction using selenium dioxide as the dehydrogenating agent. The dehydrogenation reaction may be carried out in the presence of a suitable organic solvent.Type: GrantFiled: September 11, 1975Date of Patent: December 13, 1977Assignee: Gist-Brocades N.V.Inventors: Cornelis Vos, Jacobus DEN Admirant, Jan Lambert VAN Os, Hendrik Marten Jongsma, Hermanus Jacobus Kooreman
-
Patent number: 4054595Abstract: Novel 18 -, 19 - and 20 -hydroxy-prostaglandin derivatives of the formula I ##STR1## wherein the dotted line in the position 8-12 indicates the optional presence of a double bond, the waved lines in position 15 indicate that the hydroxyl group and the group R.sub.4 are either in .alpha.- or .beta.-position and Z represents a -- CH.sub.2 CH.sub.2 -- or a cis -- CH=CH -- group, and wherein R represents one of the groups: ##STR2## (wherein the waved lines indicate that the hydroxyl groups are either in .alpha.- or .beta.-position and R.sub.1 represents a hydrogen atom, a methyl or ethyl group), R.sub.2 represents either an oxygen atom or a hydrogen atom and an .alpha.- or .beta.-hydroxyl group, R.sub.3 represents a hydrogen atom or a hydroxyl group and R.sub.4 represents a hydrogen atom or a methyl group, with the proviso that when simultaneously, R.sub.1, R.sub.3 and R.sub.4 each represents a hydrogen atom, R.sub.Type: GrantFiled: March 25, 1975Date of Patent: October 18, 1977Assignee: Gist-Brocades N.V.Inventors: Arthur Friedrich Marx, Jean Doodewaard
-
Patent number: 4049825Abstract: Diphenylmethoxyethylamines of the general formula ##STR1## in which R.sub.1 represents a fluorine, bromine or chlorine atom, R.sub.2 represents a hydrogen or fluorine atom and R.sub.3 represents a hydrogen, fluorine or chlorine atom, with the provisos that R.sub.3 is a hydrogen atom when R.sub.2 is a fluorine atom, R.sub.1 is a fluorine atom when R.sub.3 is a chlorine atom and R.sub.1 is a fluorine or bromine atom when R.sub.2 and R.sub.3 both are hydrogen atoms, and their non-toxic acid addition salts are disclosed. The compounds have dopaminergic properties and their use is indicated for treating the Parkinson syndrome. Compositions for such use are disclosed.Type: GrantFiled: October 20, 1976Date of Patent: September 20, 1977Assignee: Gist-Brocades N.V.Inventor: Johan Gootjes
-
Patent number: 4046761Abstract: Novel azetidine derivatives of the formula ##STR1## wherein R.sub.1 is an acylamido group, R.sub.2 is selected from the group consisting of ##STR2## wherein R.sub.4, R.sub.5 and R.sub.6 are individually selected from the group consisting of hydrogen, lower alkyl and lower alkenyl, n is 2 or 3 and -- in the case when formula IIB is a phenyl -- this group may carry 1 to 4 substituents selected from the group consisting of halogen, lower alkyl, lower alkenyl and phenyl, and R.sub.3 is lower alkyl optionally substituted with 1 or 2 phenyls which phenyl groups may be substituted with nitro and a process for their preparation and process for the preparation of cephalosporanic acid derivatives using the azetidines of formula I as intermediates.This is a division of Serial No. 547,948, filed Feb. 7, 1975 now Pat. No. 4,007,202.Type: GrantFiled: March 4, 1976Date of Patent: September 6, 1977Assignee: Gist-Brocades N.V.Inventors: Jan Verweij, Hong Sheng Tan
-
Patent number: 4035352Abstract: Novel 6-substituted amino-penicillanic acid anhydrides useful in the process for the preparation of 7-substituted amino-desacetoxycephalosporanic derivatives comprising converting a 6-substituted amino-penicillanic acid sulfoxide into an anhydride of a 6-substituted amino-penicillanic acid sulfoxide, heating the said acid anhydride intermediate at a temperature up to at most 160.degree. C in a dry inert organic solvent with an anhydrous acid which is capable of causing ring expansion of the penam ring to a .DELTA..sup.3 -cephem ring, in the presence of a silicon-containing compound capable of (a) removing water formed during the ring enlargement of the penam structure fast enough to prevent water hydrolysis of the acid anhydride moiety present and (b) forming neutral or basic products on hydrolysis, the aforesaid acid being strong enough not to be, or not to a substantial extent to be, silylated under the reaction conditions employed, and hydrolyzing the resulting compound in situ to form the .DELTA..sup.Type: GrantFiled: May 6, 1975Date of Patent: July 12, 1977Assignee: Gist-Brocades N.V.Inventors: Jan Verweij, Hong Sheng Tan, Hermanus Jacobus Kooreman
-
Patent number: 4024129Abstract: A process for the preparation of acylamido derivatives by reaction of a compound of the formula Z - N = C = O, wherein Z is an optionally substituted alkyl-, aryl- (preferably phenyl or naphthyl) or cycloalkyl or optionally substituted heterocyclic, preferably a penicillanic acid or a cephalosporanic acid nucleus, having carboxyl groups and an optionally present hydroxy group protected, with a carboxylic acid of the formula ##STR1## wherein Z.sup.1 is an optionally substituted hydrocarbon group, in the presence of a catalyst selected from the group consisting of substituted pyridines and their N-oxides, optionally substituted imidazoles or their N-oxides, optionally substituted benzimidazoles or their N-oxides, and optionally substituted imidazo [1,2-.alpha.] pyridines or their N-oxides.Type: GrantFiled: November 3, 1971Date of Patent: May 17, 1977Assignee: Gist-Brocades N.V.Inventors: Peter Wolfgang Henniger, Antoon Van Harrewijn