Oxygen Bonded Directly At The 14- Or 15-position Patents (Class 552/563)
  • Patent number: 6080878
    Abstract: 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: Grant
    Filed: April 29, 1998
    Date of Patent: June 27, 2000
    Assignee: 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
  • Patent number: 6030962
    Abstract: This invention provides Vitamin D.sub.3 analogs of the Formula I ##STR1## wherein: X is H.sub.2 or CH.sub.2 ;Y is hydrogen, hydroxy or fluorine;Z is hydroxy;R.sub.1 and R.sub.2 are a (C.sub.1 -C.sub.4) alkyl or fluoroalkyl, or R.sub.1 and R.sub.2 together with C.sub.25 form a (C.sub.3 -C.sub.6) cycloalkyl or cyclofluoroalkyl;R.sub.3 and R.sub.4 are a (C.sub.1 -C.sub.4) alkyl or fluoroalkyl, or R.sub.3 and R.sub.4 together with C.sub.25, form a (C.sub.3 -C.sub.6)cycloalkyl or cyclofluoroalkyl;A is a single bond or a double bond;B.sub.1 is a single bond, an E-double bond, a Z-double bond or a triple bond; andB.sub.2 is a single bond, an E-double bond, a Z-double bond or a triple bond; and prodrugs thereof, intermediates and methods for preparation of these analogs, pharmaceutical compositions containing such analogs and methods for treatment of osteoporosis, hyperparathyroidism and autoimmune diseases.
    Type: Grant
    Filed: April 16, 1998
    Date of Patent: February 29, 2000
    Assignee: Synttex (U.S.A.) Inc.
    Inventors: Percy Sarwood Manchand, Milan Radoje Uskokovic
  • Patent number: 5756489
    Abstract: 18,19-dinor-vitamin D.sub.3 analogs in which the angular methyl group attached to carbon 13 of the CD-ring and the exocyclic methylene group attached to carbon 10 of the A-ring have been removed and replaced by a hydrogen atom. The 18,19-dinor vitamin D compounds are characterized by relatively high cell differentiation activity, and marked intestinal calcium transport activity while exhibiting lower activity than 1.alpha.,25-dihydroxyvitamin D.sub.3 in their ability to mobilize calcium from bone. These compounds would be useful for the treatment of diseases where bone formation is desired, such as osteoporosis, because of their preferential calcemic activity, and for the treatment of psoriasis due to their cell differentiation activity.
    Type: Grant
    Filed: April 16, 1997
    Date of Patent: May 26, 1998
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Rafal R. Sicinski, Kato L. Perlman
  • Patent number: 5710293
    Abstract: The present invention relates to a method of using a perchloric acid catalyzed reaction to make acyl derivatives of norprogesterone compounds and, in particular, 16-methylene-17.alpha.-hydroxy-19-norpregn-4-ene-3,20-dione.
    Type: Grant
    Filed: October 13, 1995
    Date of Patent: January 20, 1998
    Assignee: The Population Council, Center for Biomedical Research
    Inventor: Fang Li
  • Patent number: 5599806
    Abstract: The invention describes hydrazino and hydroxyamino-14.beta.-hydroxyandrostane derivatives having general formula (I): ##STR1## wherein the symbol means .alpha. or .beta. configuration and A, B, R.sup.1, R.sup.2, R.sup.3, and R.sup.4 have the meanings given in the description and their use in the treatment of cardiovascular disorders such as heart failure and hypertension.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: February 4, 1997
    Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.
    Inventors: Alberto Cerri, Giuseppe Bianchi, Patrizia Ferrari, Elena Folpini, Piero Melloni
  • Patent number: 5583127
    Abstract: Disclosed are 17-iminomethylalkenyl and 17-iminoalkyl-14.beta.-hydroxy-5.beta.-androstane derivatives of the formula (I): ##STR1## wherein the symbol means .alpha. or .beta. configuration or a Z or E configuration; A represents (CH.sub.2).sub.m or --(CH.dbd.CH).sub.n --; m represents an integer number from 1 to 6; n represents an integer number from 1 to 3; R.sup.2 represents hydrogen or hydroxy; R.sup.1 represents hydrogen, C.sub.2 -C.sub.4 alkyl unsubstituted or substituted by NR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5, which may be the same or different, represent hydrogen, C.sub.1 -C.sub.4 alkyl or R.sup.4 and R.sup.5 may form, when taken together with the nitrogen atom, a five- or six- membered heterocyclic ring optionally containing one or more heteroatoms selected from oxygen and nitrogen; R.sup.3 represents NHC(.dbd.X)NR.sup.6 R.sup.7 or OR.sup.8 wherein R.sup.6 and R.sup.7, which may be the same or different, represent hydrogen, methyl, or C.sub.2 -C.sub.4 alkyl unsubstituted or substituted by NR.
    Type: Grant
    Filed: December 23, 1994
    Date of Patent: December 10, 1996
    Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.
    Inventors: Alberto Cerri, Giuseppe Bianchi, Patrizia Ferrari, Elena Folpini, Piero Melloni
  • Patent number: 5444055
    Abstract: 17-hydroxyiminomethyl-14.beta.-hydroxy-5.beta.
    Type: Grant
    Filed: August 16, 1993
    Date of Patent: August 22, 1995
    Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.
    Inventors: Alberto Cerri, Luigi Bernardi, Giuseppe Bianchi, Monica Florio, Elena Folpini, Piero Melloni
  • Patent number: 5352808
    Abstract: A process for the preparation of a compound of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms optionally substituted by halogen or a nitrogen or oxygen function and alkenyl and alkynyl of 2 to 4 carbon atoms, R.sub.2 is alkyl of 1 to 4 carbon atoms and the A, B, C and D rings are optionally substituted by at least one member of the group consisting of optionally protected --OH or .dbd.0, halogen, alkyl and alkoxy of 1 to 4 carbon atoms and alkenyl and alkynyl of 2 to 4 carbon atoms comprising reacting a compound of the formula ##STR2## wherein R.sub.1 and R.sub.2 and the A, B, C and D rings are defined as above with an oxidizing agent in the presence of water and an at least partially water-miscible solvent to obtain a compound of the formula ##STR3## wherein R.sub.1 and R.sub.
    Type: Grant
    Filed: November 5, 1992
    Date of Patent: October 4, 1994
    Assignee: Roussel Uclaf
    Inventors: Jean Buendia, Michel Vivat
  • Patent number: 5093502
    Abstract: A process for the preparation of novel 14.alpha., 17.alpha.-dihydroxy-17.beta.-substituted steroids by reacting 14.alpha.-hydroxy-17-oxo-steroids with metal organic compounds and the use of the said novel steroids in the production of 14.alpha., 17.alpha.-methylenedioxy-pregnane derivatives.
    Type: Grant
    Filed: February 16, 1990
    Date of Patent: March 3, 1992
    Assignee: Akzo N.V.
    Inventors: Peter M. Smid, Willem J. Van Zoest, Pieter G. Weber, Arthur F. Marx
  • Patent number: 5028722
    Abstract: Novel 7.beta.-hydroxy-4-pregnene-3,20-dione derivatives are disclosed.The group of these compounds has possibility of being utilized as an intermediate for the synthesis of progesterone derivatives having ovulation-inhibiting activity. These compounds themselves have also cell differentiation activity for M1 cells.
    Type: Grant
    Filed: September 26, 1988
    Date of Patent: July 2, 1991
    Assignee: Snow Brand Milk Products Co., Ltd.
    Inventors: Makoto Yoshihama, Koji Tamura, Nobuo Miyata, Masamichi Nakakoshi