Patents by Inventor Sebastianus J. Halkes
Sebastianus J. Halkes has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 6288249Abstract: The invention relates to vitamin D analogs of general formula (I) wherein: R1 is a hydrogen atom or a substituent selected from the group consisting of hydroxy, CH2OH, CH2CH2OH, CH2CH2CH2OH, OCH3, OCH2OH, OCH2CH2OH and OCH2CH2CH2OH; R2 is a hydrogen atom or a substituent selected from the group consisting of OCH3, OCH2OH, CHm(CH2OH)n(CH2CH2OH)p, (CH2)qOH and O(CH2)rOH; wherein: m is 0 or 1, p, q and n are 0-3, r is 1-3 and m+n+p=3; with the proviso that R1 and/or R2 contain at least one OH group; R3 is a straight or branched, saturated or unsaturated aliphatic hydrocarbon of 6-13 C atoms which may be substituted with one or more substituents from the group hydroxy or fluoro. The invention further relates to methods of preparing these compounds, a pharmaceutical composition containing these compounds and to their use in pharmacotherapy and cosmetics.Type: GrantFiled: June 16, 1999Date of Patent: September 11, 2001Assignee: Kingdom of the NetherlandsInventors: Sebastianus J. Halkes, Jan Paul Van De Velde, Silvia Kanzler, Wolfgang Reischl
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Patent number: 6080878Abstract: The invention relates to a new method of preparing 16-dehydro vitamin D compounds having formula I ##STR1## wherein: R has the epi-configuration or the normal configuration and represents straight or branched C.sub.1-6 -alkyl, C.sub.2-6 -alkenyl, C.sub.3-6 -cycloalkyl, or an aromatic group optionally substituted with halogen, C.sub.1-3 -alkyl or alkoxy,Z is a saturated or unsaturated straight hydrocarbon group or oxahydrocarbon group containing 3-6 C-atoms which may be substituted with OH, F, alkyl (C.sub.1-3) or cycloalkyl (C.sub.3-5),R.sub.1 is hydrogen or an hydroxy protecting group,R.sub.2 is hydrogen or hydroxy, andA and B represent hydrogen or methyl, or together form the methylene group, to the new compounds having this formula and to new intermediates obtainable according to this process.Type: GrantFiled: April 29, 1998Date of Patent: June 27, 2000Assignee: Duphar International Research B.V.Inventors: Maria de los Angeles Rey, Antonio Mourino, Ana Fernandez-Gacio, Yagamare Fall, Sebastianus J. Halkes, Koen M. Halkes, Jan-Paul van de Velde, Jan Zorgdrager
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Patent number: 6075015Abstract: Vitamin D.sub.3 analogues of the formula (I): ##STR1## wherein R.sub.1 is hydrogen or hydroxy, R.sub.2 is (C.sub.1 -C.sub.3)alkyl, hydroxy(C.sub.1 -C.sub.3)alkyl, (C.sub.1 -C.sub.2)alkoxymethyl, (C.sub.2 -C.sub.3)alkenyl, or (C.sub.2 -C.sub.3)alkynyl, R.sub.3 is a branched or unbranched, saturated or unsaturated aliphatic 3- to 5- membered hydrocarbon or oxahydrocarbon biradical, having at least 3 atoms in the main chain and being optionally substituted with one or more substituents selected from epoxy, fluoro and hydroxy, R.sub.4 is sec. or tert. (C.sub.3 -C.sub.6)alkyl or (C.sub.3 -C.sub.6)cycloalkyl, A and B are each individually hydrogen or methyl, or A and B together from methylene.Type: GrantFiled: May 27, 1997Date of Patent: June 13, 2000Assignee: Duphar International Research B.V.Inventors: Jose P. Sestelo, Antonio Mourino, Jose L. Mascarenas, Sebastianus J. Halkes, Jan Zorgdrager, Gerhardus D. H. Dijkstra, Jan-Paul van de Velde
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Patent number: 6072062Abstract: The invention relates to a new vitamin D compound, substituted in the 18-position with an alkyl group, a hydroxy group, an alkoxy group, an alkenyl group, an alkynyl group, a fluorinated alkyl group or a fluorinated alkenyl group. The invention also relates to a method of preparing said vitamin D compound and to a lactone and a hydrindane intermediate.Type: GrantFiled: February 13, 1997Date of Patent: June 6, 2000Assignee: Duphar International Research B.V.Inventors: Maria J. Valles, Jose L. Mascarenas, Antonio Mourino, Sebastianus J. Halkes, Jan Zorgdrager
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Patent number: 5929056Abstract: The present invention relates to vitamin D compounds of the general formula ##STR1## wherein: R.sub.1 is a hydrogen atom or a hydroxy group;R.sub.2 is a (C.sub.1 -C.sub.3)alkyl group, a hydroxy(C.sub.1 -C.sub.3)alkyl group, a (C.sub.1 -C.sub.2)alkoxymethyl group or a (C.sub.2 -C.sub.3)alkenyl or alkynyl group;n is 1;R.sub.3 is a branched or non-branched, saturated or unsaturated, substituted or unsubstituted aliphatic (C.sub.3 -C.sub.7)hydrocarbon or oxyhydrocarbon biradical;R.sub.4 is a branched or straight (C.sub.1 -C.sub.6) alkyl group or a (C.sub.3 -C.sub.6)cycloalkyl group; andA and B are each individually hydrogen atoms or methyl groups, orA and B form together a methylene group.The present compounds find use in cosmetic application and in human and veterinary pharmacotherapeutic practice in the treatment of skin and bone diseases, diseases related to cell differentiation/cell proliferation, imbalance in the immune system and inflammatory diseases.Type: GrantFiled: December 11, 1995Date of Patent: July 27, 1999Assignee: Duphar International Research B.V.Inventors: Antonio Mourino, Jose Antonio Martinez, Maria de los Angeles Rey, Juan Granja, Sebastianus J. Halkes
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Patent number: 5637742Abstract: The invention relates to a new vitamin D compound, substituted in the 18-position with an alkyl group, a hydroxy group, an alkoxy group, an alkenyl group, an alkynyl group, a fluorinated alkyl group or a fluorinated alkenyl group.The invention also relates to a method of preparing said vitamin D compound and to a lactone and a hydrindane intermediate.Type: GrantFiled: November 1, 1994Date of Patent: June 10, 1997Assignee: Duphar International Research B.V.Inventors: Maria J. Valles, Jose L. Mascarenas, Antonio Mourino, Sebastianus J. Halkes, Jan Zorgdrager
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Patent number: 5449668Abstract: The invention relates to a new vitamin D compound of the general formula ##STR1## wherein: R.sub.1 is a hydrogen atom or a hydroxy group;R.sub.2 is a (C.sub.1 -C.sub.3)alkyl group, a hydroxy(C.sub.1 -C.sub.3)alkyl group, a (C.sub.1 -C.sub.2)alkoxymethyl group or a (C.sub.2 -C.sub.3)alkenyl or alkynyl group;R.sub.3 is a branched or non-branched, saturated or unsaturated aliphatic 3- to 5 -membered hydrocarbon or oxahydrocarbon biradical, having at least 3 atoms in the main chain and being optionally substituted with one or more substituents selected from epoxy, fluoro and hydroxy;R.sub.4 is a sec. or tert. (C.sub.3 -C.sub.6)alkyl group or a (C.sub.3 -C.sub.6)cycloalkyl group; andA and B are each individually hydrogen atoms or methyl groups, orA and B form together a methylene group.The invention further relates to a method of preparing these compounds and to their use in pharmacotherapy and cosmetics.Type: GrantFiled: June 4, 1993Date of Patent: September 12, 1995Assignee: Duphar International Research B.V.Inventors: Jose P. Sestelo, Antonio Mourino, Jose L. Mascarenas, Sebastianus J. Halkes, Jan Zorgdrager, Gerhardus D. H. Dijkstra, Jan-Paul van de Velde
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Patent number: 5403940Abstract: The invention relates to a new vitamin D compound, substituted in the 18-position with an alkyl group, a hydroxy group, an alkoxy group, an alkenyl group, an alkynyl group, a fluorinated alkyl group or a fluorinated alkenyl group.The invention also relates to a method of preparing said vitamin D compound and to a lactone and a hydrindane intermediate.Type: GrantFiled: January 12, 1994Date of Patent: April 4, 1995Assignee: Duphar International Research B.V.Inventors: Maria J. Valles, Jose L. Mascarenas, Antonio Mourino, Sebastianus J. Halkes, Jan Zorgdrager
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Patent number: 5395953Abstract: The invention relates to a method of preparing a compound having an alkyl or alkoxyalkyl side-chain with a terminal 2-hydroxyprop-2-yl group, by oxidizing a compound having a terminal isopropyl group in its side-chain with a dioxirane as the oxidant.Type: GrantFiled: August 20, 1993Date of Patent: March 7, 1995Assignee: Duphar International Research B.V.Inventors: Miguel A. Maestro, Antonio Mourino, Benjamin Borsje, Sebastianus J. Halkes
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Patent number: 5175217Abstract: The invention relates to a method for the photochemical conversion of tachysterol compounds into previtamin D compounds and of trans-vitamin D compounds into cis-vitamin D compounds under the influence of radiation, by exposing the tachysterol compound and trans-vitamin D compound, respectively, dissolved in a suitable solvent system, in the presence of a polymeric photosensitizer consisting of a polymer chain ("backbone") comprising covalently bound sensitizers suitable for the photochemical conversion, to light with a wavelength of preferably between approx. 300 and approx.Type: GrantFiled: August 23, 1990Date of Patent: December 29, 1992Assignee: Duphar International Research B.V.Inventors: Eric Goethals, Sebastianus J. Halkes, Robert B. Koolstra
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Patent number: 5110924Abstract: The invention relates to an adduct-aldehyde of the general formula ##STR1## wherein R is a hydrogen atom or an optionally etherified or esterified hydroxy group,R.sub.1 is an optionally etherified or esterified hydroxy group, andZ is a sulphonyl group or a group of the general formula ##STR2## wherein A and B are equal or different and represent C.sub.1 -C.sub.4 alkoxy groups, or wherein A and B together constitute a phenylimino group or a o-phenylene group.The invention also relates to a method of preparing said adduct-aldehyde and to the use of said aldehyde as an intermediate for the preparation of vitamin-D compounds.Type: GrantFiled: June 12, 1990Date of Patent: May 5, 1992Assignee: Duphar International Research B.V.Inventors: Sebastianus J. Halkes, Wilhelmus R. M. Overbeek
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Patent number: 5035783Abstract: The invention relates to a method for the photochemical conversion of tachysterol compounds into previtamin D compounds and of trans-vitamin D compounds into cis-vitamin D compounds under the influence of radiation, by exposing the tachysterol compound and trans-vitamin D compound, respectively, dissolved in a suitable solvent system, in the presence of a polymeric photosensitizer consisting of a polymer chain ("backbone") comprising covalently bound sensitizers suitable for the photochemical conversion, to light with a wavelength of preferably between approx. 300 and approx.Type: GrantFiled: December 7, 1989Date of Patent: July 30, 1991Assignee: Duphar International Research B.V.Inventors: Eric Goethals, Sebastianus J. Halkes, Robert B. Koolstra
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Patent number: 4539153Abstract: The invention relates to a method of preparing 1 .alpha.-hydroxyvitamin D or 1 .alpha.-hydroxy-previtamin D compounds by hydroxylating the 1 .alpha.-position of an adduct of a previtamin D compound with a suitable dienophile, in which adduct optionally present hydroxy group or hydroxy groups is or are protected, if desired, and after removal of the protecting group or groups, isolating the 1 .alpha.-hydroxyvitamin D or 1 .alpha.-hydroxy-previtamin D compound.The invention also relates to 1 .alpha.-hydroxy-previtamin D compounds.The invention further relates to an adduct of a previtamin D or tachysterol compound with a dienophile of the general formula ##STR1## in which A' and B' are equal and represent methoxy groups or ethoxy groups, or in which A' and B' together constitute a phenylimino or o-phenylene group.Type: GrantFiled: July 31, 1984Date of Patent: September 3, 1985Assignee: Duphar International Research B.V.Inventors: Maurits Vandewalle, Luc J. Vanmaele, Pierre J. De Clercq, Sebastianus J. Halkes, Wilhelmus R. M. Overbeek
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Patent number: RE36854Abstract: The invention relates to a new vitamin D compound of the general formula ##STR1## wherein: R.sub.1 is a hydrogen atom or a hydroxy group;R.sub.2 is a (C.sub.1 -C.sub.3)alkyl group, a hydroxy(C.sub.1 -C.sub.3)alkyl group, a (C.sub.1 -C.sub.2)alkoxymethyl group or a (C.sub.2 -C.sub.3)alkenyl or alkynyl group;R.sub.3 is a branched or non-branched, saturated or unsaturated aliphatic 3- to 5 -membered hydrocarbon or oxahydrocarbon biradical, having at least 3 atoms in the main chain and being optionally substituted with one or more substituents selected from epoxy, fluoro and hydroxy;R.sub.4 is a sec. or tert. (C.sub.3 -C.sub.6)alkyl group or a (C.sub.3 -C.sub.6)cycloalkyl group; andA and B are each individually hydrogen atoms or methyl groups, orA and B form together a methylene group.The invention further relates to a method of preparing these compounds and to their use in pharmacotherapy and cosmetics.Type: GrantFiled: September 15, 1997Date of Patent: September 5, 2000Assignee: Duphar International Research B.V.Inventors: Jose P. Sestelo, Antonio Mourino, Jose L. Mascarenas, Sebastianus J. Halkes, Jan Zorgdrager, Gerhardus D. H. Dijkstra, Jan-Paul van de Velde