Patents Examined by Kimberly J. Kestler
  • Patent number: 5420272
    Abstract: The invention provides compounds of the formula: ##STR1## wherein R, R.sup.3, R.sup.4, X and W are defined in the specification. These compounds are useful as antibiotic agents.
    Type: Grant
    Filed: August 13, 1992
    Date of Patent: May 30, 1995
    Assignee: American Cyanamid Company
    Inventors: Phaik-Eng Sum, Ving J. Lee, Joseph J. Hlavka, Raymond T. Testa
  • Patent number: 5418227
    Abstract: 14,16.beta.-Ethano-15.beta.,16.sup.1 -cyclo-14.beta.-estra-1,3,5(10)-trienes of general formula I ##STR1## in which R.sup.1 means a hydrogen atom, a C.sub.1 to C.sub.9 alkyl or C.sub.1 to C.sub.9 acyl radical,R.sup.2 means a hydrogen atom, a C.sub.1 to C.sub.9 alkyl radical, a C.sub.2 to C.sub.9 alkenyl or alkinyl radical andR.sup.3 means a hydroxy group or a C.sub.1 to C.sub.9 acyloxy radical, as well as a process for their production are described. The new compounds have high (peroral) effectiveness and are suitable for the production of pharmaceutical agents.
    Type: Grant
    Filed: November 15, 1993
    Date of Patent: May 23, 1995
    Assignee: Schering Aktiengesellschaft
    Inventors: James R. Bull, Walter Elger, Krzysztof Chwalisz, Karl-Heinrich Fritzemeier
  • Patent number: 5416227
    Abstract: The invention includes printing ink compositions containing an organic solution of a film-forming polymer and a dye salt of formula ##STR1## wherein R is a group of formula ##STR2## wherein R.sub.1 is C.sub.1 -.sub.4 alkyl, R.sub.2 and R.sub.3 are each independently of the other hydrogen, CH.sub.2 X, SO.sub.2 Y or NHCOZ, R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl and R.sub.5 is CH.sub.2 X, SO.sub.2 Y or NHCOZ, X is a NHCOR.sub.6 or NR.sub.7 SO.sub.2 R.sub.6 group, Y is NR.sub.8 R.sub.9 or N(R.sub.8).sub.2, and Z is C.sub.1 -C.sub.4 alkyl or NHR.sub.9, R.sub.6 is C.sub.1 -C.sub.4 alkyl, unsubstituted phenyl or phenyl which is substituted by C.sub.1 -C.sub.4 alkyl or halogen, R.sub.7 is hydrogen or C.sub.1 -C.sub.4 alkyl and R.sub.8 is hydrogen, C.sub.1 -C.sub.4 alkyl or a ##STR3## group, and R.sub.9 is hydrogen C.sub.1 -C.sub.4 alkyl or phenyl, and R', R" and R"' are alkyl radicals containing together 10 to 24 carbon atoms, or a mixture of such dye salts.
    Type: Grant
    Filed: February 14, 1994
    Date of Patent: May 16, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Martin Tanner, Dieter Mausezahl, Paul Lienhard, Robert von Arx
  • Patent number: 5414098
    Abstract: The invention provides new 24, 26, and/or 27 homologated vitamin D.sub.2 compounds, such as 26,27-dihomo-1.alpha.-hydroxyvitamin D.sub.2, 26,27-dihomo-1.alpha.-hydroxy-24-epi-vitamin D.sub.2, 26,27-dihomo-1.alpha.,25-dihydroxy-24-epi-vitamin D.sub.2 and certain hydroxy-protected derivatives thereof. The new epi compounds in particular exhibit a distinctive activity pattern comprising high potency in stimulating intestinal calcium transport and little or no activity in inducing bone calcium mobilization or the differentiation of undifferentiated cells in culture, thereby evincing utility in the treatment of diseases characterized by loss of bone mass. In contrast, the natural form exhibits no activity in either mobilizing calcium from bone or stimulating intestinal calcium transport. A process for preparing such compounds is also disclosed.
    Type: Grant
    Filed: December 3, 1992
    Date of Patent: May 9, 1995
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman
  • Patent number: 5411949
    Abstract: 23-Oxa-derivatives in the vitamin D series of formula I ##STR1## are described in which R.sup.1, R.sup.2 and R.sup.4 independently of one another mean a hydrogen atom or an acyl group with 1 to 9 carbon atoms,R.sup.3 each means a hydrogen atom or each a linear or branched alkyl group with 1 to 4 carbon atoms and X means an alkylene radical--(CH.sub.2).sub.n -- with n=1, 2, 3, and if n=1, R.sup.3 each cannot be a methyl or propyl group, as well as a process for their production.The compounds have proliferation-inhibiting and cell-differentiation effects and are suitable for the production of pharmaceutical agents.
    Type: Grant
    Filed: July 19, 1993
    Date of Patent: May 2, 1995
    Assignee: Schering Aktiengesellschaft
    Inventors: Gunter Neef, Andreas Steinmeyer, Gerald Kirsch, Katica Schwarz, Martin Haberey, Ruth Thieroff-Ekerdt, Petra Rach
  • Patent number: 5412091
    Abstract: A compound of the formula ##STR1## in which ##STR2## is either a 3-keto-.DELTA.4-system or a 3-keto -.DELTA.1,4-system or a 3-OR.sub.4 - .DELTA.5-system in which R.sub.4 is hydrogen or a protector group of hydroxy, R is methyl --CH.sub.2 OH or --CH.sub.2 OR', in which R' is a protector group of hydroxy, R.sub.1 and R'.sub.1 are individually selected from the group consisting of methyl, a branched alkyl not possessing hydrogen in the .beta. position of 5 to 8 carbon atoms, aryl of up to 10 carbon atoms, heteroaryl of up to 10 carbon atoms and at least one heteroatom chosen from nitrogen, sulfur and oxygen and benzyl, n and m, are individually numbers 0 or 1, R.sub.2 and R.sub.3 are hydrogen or R.sub.2 is fluorine and R.sub.3 is formyloxy or acetyloxy and the dotted lines in position 9(11) indicate the optional presence of a second bond which is useful for the preparation of compounds of formula A.
    Type: Grant
    Filed: July 1, 1993
    Date of Patent: May 2, 1995
    Assignee: Roussel Uclaf
    Inventors: Jean Boivin, Christine Chauvet, Samir Zard
  • Patent number: 5407928
    Abstract: This invention relates to 11.beta.-aryl-gona-4,9-dienes of the general formula I ##STR1## wherein the variables are defined in the specification. The compounds are progesterone antagonists and are suitable for inducing labor or an abortion.
    Type: Grant
    Filed: November 17, 1993
    Date of Patent: April 18, 1995
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Kasch, Gudrun Bertram, Kurt Ponsold, Gerd Schubert, Heidemarie Rohrig, Anatoli Kurischko, Bernd Menzenbach
  • Patent number: 5403832
    Abstract: A vitamin D.sub.3 analogue which includes a hydroxyalkyl substituent in the 1-position and a modified D-ring side chain is described. This novel compound is a potent anti-proliferative substance with activity comparable to that of calcitriol but with a vitamin D.sub.3 receptor binding rating of approximately 10.sup.-3 compared to that of calcitriol.
    Type: Grant
    Filed: August 2, 1994
    Date of Patent: April 4, 1995
    Assignee: The Johns Hopkins University
    Inventors: Gary H. Posner, Maria-Christina White
  • Patent number: 5403940
    Abstract: 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: Grant
    Filed: January 12, 1994
    Date of Patent: April 4, 1995
    Assignee: Duphar International Research B.V.
    Inventors: Maria J. Valles, Jose L. Mascarenas, Antonio Mourino, Sebastianus J. Halkes, Jan Zorgdrager
  • Patent number: 5401733
    Abstract: The invention relates to the compounds 1,25-dihydroxy-16-ene-24-oxo-cholecalciferol and 1,24,25-trihydroxy-16-ene-cholecalciferol which stimulate differentiation of HL-60 cells, rendering them useful as an agent for the treatment of neoplastic diseases such as leukemia, and also decrease proliferation of human keratinocytes, rendering them useful as an agent for the treatment of hyperproliferative disorders of the skin such as psoriasis.
    Type: Grant
    Filed: October 1, 1993
    Date of Patent: March 28, 1995
    Assignees: Hoffmann-La Roche Inc., Satyanarayama G. Reddy
    Inventors: John A. McLane, Satyanarayama G. Reddy, Milan R. Uskokovic
  • Patent number: 5401731
    Type: Grant
    Filed: August 30, 1993
    Date of Patent: March 28, 1995
    Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Productionsaktieselskab)
    Inventors: Martin J. Calverley, Ernst T. Binderup
  • Patent number: 5401732
    Type: Grant
    Filed: February 11, 1993
    Date of Patent: March 28, 1995
    Assignee: Leo Pharmaceutical Products Ltd. A/S Kemiske Fabrik Produkionsaktiese SKAB
    Inventors: Martin J. Calverley, Kai Hansen, Lise Binderup
  • Patent number: 5401729
    Abstract: The invention provides compounds of the formula: ##STR1## wherein R, R.sup.3, R.sup.4 and W are defined in the specification. These compounds are useful as antibiotic agents.
    Type: Grant
    Filed: February 24, 1994
    Date of Patent: March 28, 1995
    Assignee: American Cyanamid Company
    Inventors: Phaik-Eng Sum, Ving J. Lee, Raymond T. Testa
  • Patent number: 5399685
    Abstract: A process for the preparation of a compound of the formula ##STR1## wherein R.sub.1 is alkyl of 1 to 3 carbon atoms, R.sub.2 is alkyl of 1 to 12 carbon atoms, R.sub.3 is alkyl of 1 to 4 carbon atoms comprising reacting a compound of the formula ##STR2## wherein R.sub.4 is a remainder of an easily cleavable ether, K is a protected ketone function in the form of ketal, thioketal or mixed ketal and R.sub.1 has the above definition with a magnesium organic compound reagent of the formulaHalMg--CH.sub.2 --R.sub.2 Awherein Hal is a halogen and R.sub.2 is defined as above to obtain a compound of the formula ##STR3## wherein R.sub.1, R.sub.2 and K are defined as above, reacting the latter with an acylation agent to obtain a compound of the formula ##STR4## wherein R.sub.5 is alkyl of 1 to 6 carbon atoms or aryl of 6 to 10 carbon atoms and R.sub.1, R.sub.2 and K are defined as above, reacting the latter with an appropriate alkylation agent to obtain a compound of the formula ##STR5## wherein R.sub.1, R.sub.2, R.sub.
    Type: Grant
    Filed: June 11, 1993
    Date of Patent: March 21, 1995
    Assignee: Roussel-Uclaf
    Inventors: Jean Buendia, Veronique Crocq, Christian Masson, Denis Prat, Michel Vivat
  • Patent number: 5397775
    Abstract: Vitamin D.sub.2 analogs in which a cyclopentane ring is introduced onto the 25-carbon of the side chain of 1.alpha.,25-dihydroxyvitamin D.sub.2 and its 24-epimer. The compounds are characterized by a marked intestinal calcium transport activity while exhibiting much lower activity than 1.alpha.,25-dihydroxyvitamin D.sub.3 in their ability to mobilize calcium from bone. Because of their preferential calcemic activity, these compounds would be useful for the treatment of diseases where bone formation is desired, such as osteoporosis.
    Type: Grant
    Filed: June 2, 1993
    Date of Patent: March 14, 1995
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. De Luca, Naoshi Nakagawa
  • Patent number: 5395831
    Abstract: This invention relates to 8.alpha.-3-hydroxyestra- 1,3,5( 10),9( 11 )tetraen-17-one (.DELTA.9( 11 )-dehydro-8-isoestrone) (VI), ##STR1## to the process for its preparation, to pharmaceutical compositions containing said 8.alpha.-3-hydroxyestra- 1,3,5(10), 9(11)tetraen-17-one (.DELTA.9(11)-dehydro-8-isoestrone) (VI) and to the use of said 8.alpha.-3-hydroxyestra-1,3,5(10),9(11 )tetraen-17-one (A9( 11 )-dehydro-8-isoestrone) (VI) for modifying the balance between bone production and bone resorption, and as an antioxidant in a host animal, including man.
    Type: Grant
    Filed: April 8, 1994
    Date of Patent: March 7, 1995
    Assignee: American Home Products Corporation
    Inventors: Frederick O. Gemmill, Jr., Chester E. Orzech, Steven J. Adelman
  • Patent number: 5393898
    Abstract: Diacetylrhein which is substantially free of aloe-emodin components, is prepared by a process whereina) rhein-9-anthrone-8-glusoside containing aloe-emodin components is subjected to a liquid-liquid partitioning of the compounds obtained is carried out between a polar organic solvent which is only partly miscible with water and an aqueous phase,b) the rhein-9-anthrone-8-glucoside contained after the partitioning in the aqueous phase is oxidized to rhein-8-glucoside,c) the glucose residue in the 8-position of the rhein-8-glucoside is split off in an acidic medium and,d) the rhein obtained is acetylated and the diacetylrhein recovered.
    Type: Grant
    Filed: April 28, 1994
    Date of Patent: February 28, 1995
    Assignee: Madaus AG
    Inventors: Alfons Carcasona, Wolf Grimminger, Pentti Hietala, Helga Zaeske, Klaus Witthohn
  • Patent number: 5391755
    Abstract: A convergent synthesis of 19-nor-vitamin D compounds, specifically 19-nor-1.alpha.,25-dihydroxyvitamin D.sub.3, is disclosed. The synthesis can also readily be utilized for preparing other 1.alpha.-hydroxylated 19-nor-vitamin D compounds. The key step in the synthesis is a suitable application of Lythgoe's procedure i.e. a Horner-Wittig reaction of the lithium anion of a phosphine oxide with a Windaus Grundmann ketone to give, after any necessary deprotection, the desired 19-nor-vitamin D compound.
    Type: Grant
    Filed: January 13, 1994
    Date of Patent: February 21, 1995
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman, Rolf E. Swenson
  • Patent number: 5391775
    Abstract: The present invention provides a process for obtaining diacetylrhein, wherein diacetylrhein containing aloe-emodin components is subjected to a liquid-liquid partitioning between a polar organic solvent which is only partly miscible with water and an aqueous phase of pH 6.5. to 7.5 and the diacetylrhein is recovered and optionally recrystallised.The present invention is also concerned with diacetylrhein obtainable by this process and with pharmaceutical compositions containing it.
    Type: Grant
    Filed: April 29, 1994
    Date of Patent: February 21, 1995
    Assignee: Madaus AG
    Inventors: Alfons Carcasona, Wolf Grimminger, Pentti Heitala, Klaus Witthohn, Helga Zaeske
  • Patent number: 5391777
    Abstract: A method is provided for isolating 5,7-diene-containing steroids, particularly 3.beta.-ols and esters of 3.beta.-ols, from a sterol mixture. The method involves (1) treating the mixture with a dienophile or with an oxidizable dienophile precursor in combination with an oxidizing agent so as to provide a Diels-Alder adduct of the 5,7-diene to be isolated, followed by (2) removal of the adduct from the mixture and (3) regeneration of the 5,7-diene with a suitable reducing agent. The invention also encompasses subsequent purification steps and intermediate modification of the Diels-Alder intermediate, e.g., wherein chemical conversion of the Diels-Alder adduct is effected prior to regeneration of the 5,7-diene. Novel compounds which are Diels-Alder adducts of 5,7-diene-containing steroids are provided as well.
    Type: Grant
    Filed: November 12, 1993
    Date of Patent: February 21, 1995
    Assignee: SRI International
    Inventors: Masato Tanabe, John G. Johansson, Dennis Yasuda