Patents by Inventor Klaus Annen

Klaus Annen 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).

  • Publication number: 20090012321
    Abstract: The present invention relates to a process for preparing 17?-acetoxy-6-methylenepregn-4-ene-3,20-dione (4) as an intermediate, and to processes for preparing medroxyprogesterone acetate (1) (17?-acetoxy-6?-methylpregn-4-ene-3,20-dione) and megestrol acetate (2) (17?-acetoxy-6-methylpregna-4,6-diene-3,20-dione) via this intermediate (4).
    Type: Application
    Filed: June 5, 2008
    Publication date: January 8, 2009
    Inventors: Klaus ANNEN, Thomas Linz, Karl-Heinz Neff, Rolf Bohlmann, Henry Laurent
  • Patent number: 4956482
    Abstract: Known pregnane derivatives are prepared by esterification of know androstane derivatives to give new esters of Formula III ##STR1## wherein in each case symbolizes a single bond or a double bond,n is 1 or 2,R.sub.1 is hydrogen or methyl,R.sub.2 is hydrogen or formyl, andR.sub.3 is chlorine, hydroxy or an alkanoyloxy group of up to 6 carbon atoms,and reaction of the latter with Ag(I) and formic acid.
    Type: Grant
    Filed: March 20, 1989
    Date of Patent: September 11, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Hofmeister, Klaus Annen, Henry Laurent, Rudolf Wiechert
  • Patent number: 4945064
    Abstract: Estrane and androstane derivatives of formula I ##STR1## wherein X is bromine, iodine, triphenyltin or trialkyltin of 1 to 6 carbon atoms per alkyl radical,Y represents two hydrogen atoms or methylene,Z represents two hydrogen atoms, oxo or alkylenedioxy of 2 to 6 carbon atoms andV is ethylene, vinylene, 1,3-propylene or cyclopropylene,R.sub.1 is hydrogen or a hydrocarbon radical of up to 8 hydrocarbon atoms, optionally interrupted by an oxa group or substituted by an oxo group,R.sub.2 is methyl or ethyl,R.sub.3 and R.sub.4 represent a carbon-carbon bond or R.sub.3 is hydrogen and R.sub.4 is hydrogen or methyl,.DELTA.symbolizes a 4(5)-double bond if Z signifies two hydrogen atoms or an oxo group; or a 5(6)-double bond or, for the estrane derivatives of formula I, also a 5(10)-double bond, if Z is alkylenedioxy,are pharmacologically effective substances or intermediates for preparation thereof.
    Type: Grant
    Filed: January 19, 1988
    Date of Patent: July 31, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Hofmeister, Henry Laurent, Paul E. Schulze, Klaus Annen, Rudolf Wiechert, Kunhard Pollow, Bernhard Manz, Hans-Joerg Grill
  • Patent number: 4912098
    Abstract: 6.alpha.-methylhydrocortisones of Formula I ##STR1## wherein R.sub.1 is alkanoyl of 2-6 carbon atoms or benzoyl andR.sub.2 is hydrogen or alkanoyl of 2-6 carbon atomshave valuable antiinflammatory properties.
    Type: Grant
    Filed: September 3, 1987
    Date of Patent: March 27, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Klaus Annen, Karl Petzoldt, Henry Laurent, Rudolf Wiechert, Helmut Hofmeister
  • Patent number: 4891365
    Abstract: 17-Substituted estradienes and estratrienes of Formula I ##STR1## wherein ##STR2## R is alkyl, alkenyl or cycloalkyl of up to 5 carbon atoms if ##STR3## R is hydrogen, alkyl, alkenyl or cycloalkyl of up to 5 carbon atoms if ##STR4## is a CC-single or CC-double bond, exhibit, an aldosterone-antagonistic activity and a strong gestagen potency.
    Type: Grant
    Filed: July 2, 1987
    Date of Patent: January 2, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Rudolf Wiechert, Sybille Beier, Walter Elger, Klaus Annen, Klaus Nickisch, Henry Laurent
  • Patent number: 4777165
    Abstract: 6.alpha.,16.beta.-Dimethyl corticoids of general Formula I ##STR1## wherein the bond .sub.-------- is a single bond or a double bond, andX is a hydrogen atom, a fluorine atom, a chlorine atom, or a bromine atom,Z is a hydrogen atom or, jointly with X, is a carbon-carbon bond,R.sub.1 is a formyl group, an alkanoyl group or alkoxyalkyl group of 2-8 carbon atoms, or a benzoyl group, andY is a hydrogen atom or a methyl group,are pharmacologically active compounds.
    Type: Grant
    Filed: June 17, 1987
    Date of Patent: October 11, 1988
    Assignee: Schering Aktiengesellschaft
    Inventors: Klaus Annen, Henry Laurent, Helmut Hofmeister, Rudolf Wiechert, Michael Topert
  • Patent number: 4708823
    Abstract: Known pregnane derivatives are prepared by esterificiation of known androstane derivatives to give new ester of Formula III ##STR1## wherein in each case symbolizes a single bond or a double bond,n is 1 or 2,R.sub.1 is hydrogen or methyl,R.sub.2 is hydrogen or formyl, andR.sub.3 is chlorine, hydroxy or an alkanoyloxy group of up to 6 carbon atoms,and reaction of the latter with Ag(I) and formic acid.
    Type: Grant
    Filed: September 17, 1985
    Date of Patent: November 24, 1987
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Hofmeister, Klaus Annen, Henry Laurent, Rudolf Wiechert
  • Patent number: 4701451
    Abstract: Compounds of Formula I ##STR1## wherein the bond is a single bond or a double bond,X is hydrogen, fluorine, chlorine, or bromine,R.sub.1 is formyl, alkanoyl or alkoxyalkyl each of which contains 2-8 carbon atoms, or benzoyl, andY is chlorine, hydroxy, formyl, alkanoyloxy of 2-8 carbon atoms, or benzoyloxy,have valuable anti-inflammatory properties.
    Type: Grant
    Filed: October 29, 1985
    Date of Patent: October 20, 1987
    Assignee: Schering Aktiengesellschaft
    Inventors: Klaus Annen, Henry Laurent, Helmut Hofmeister, Rudolf Wiechert, Michael Toepert, Hans Wendt
  • Patent number: 4670427
    Abstract: 1.alpha.,2.alpha.-methylene-6-methylene- and 6.alpha.-methylpregnenes of Formula I ##STR1## wherein A is ##STR2## and R is a hydrogen atom, an acyl group, or an alkoxymethyl groupare strong antiandrogens, and suitable for the topical treatment of seborrhea, acne, alopecia, and hirsutism.
    Type: Grant
    Filed: January 18, 1985
    Date of Patent: June 2, 1987
    Assignee: Schering Aktiengesellschaft
    Inventors: Klaus Annen, Henry Laurent, Walter Elger, Rudolf Wiechert, Helmut Hofmeister, Michael Topert
  • Patent number: 4645763
    Abstract: 6.alpha.-Methyl corticoids of formula I ##STR1## wherein is a single bond or a double bond, R is acyloxy of up to 8 carbon atoms, and X is chlorine, hydroxy, or acyloxy of up to 8 carbon atoms, are pharamacologically effective substances.
    Type: Grant
    Filed: November 22, 1983
    Date of Patent: February 24, 1987
    Assignee: Schering Aktiengesellschaft
    Inventors: Klaus Annen, Henry Laurent, Helmut Hofmeister, Rudolf Wiechert, Hans Wendt
  • Patent number: 4619922
    Abstract: 6.alpha.,16.alpha.-Dimethyl corticoids of general Formula I ##STR1## wherein the bond is a single bond or a double bond,X is a hydrogen atom, a fluorine atom, a chlorine atom, or a bromine atom,R.sub.1 is a formyl group, an alkanoyl group or alkoxyalkyl group of 2-8 carbon atoms, or a benzoyl group, andY is a hydrogen atom, a chlorine atom, a hydroxy group, a formyl group, an alkanoyloxy group of 2-8 carbon atoms, or a benzoyloxy group,are pharmacologically effective compounds.
    Type: Grant
    Filed: January 2, 1985
    Date of Patent: October 28, 1986
    Assignee: Schering Aktiengesellschaft
    Inventors: Klaus Annen, Henry Laurent, Helmut Hofmeister, Michael Topert
  • Patent number: 4609651
    Abstract: 11.beta.-Arylestradienes of general Formula I are disclosed ##STR1## wherein R.sup.2 is a hydrogen atom, a methyl group, or an ethyl group,R.sup.3 is a hydrogen atom or an acyl group,R.sup.1 and A-B have various meanings,which possess antigestagen and antimineralocorticoid activity.
    Type: Grant
    Filed: December 21, 1984
    Date of Patent: September 2, 1986
    Assignee: Schering Aktiengesellschaft
    Inventors: Ralph Rohde, Klaus Annen, Gunter Neef, Rudolf Wiechert, Sybille Beier, Walter Elger, David Henderson
  • Patent number: 4587236
    Abstract: 6.alpha.-Methylprednisolone derivatives of Formula I ##STR1## wherein R.sub.1 is 1-oxoalkyl of 2-6 carbon atoms or benzoyl andR.sub.2 is 1-oxoalkyl of 2-6 carbon atoms, are pharmacologically efficacious compounds, e.g., as antiinflammatories.
    Type: Grant
    Filed: October 27, 1983
    Date of Patent: May 6, 1986
    Assignee: Schering Aktiengesellschaft
    Inventors: Klaus Annen, Karl Petzoldt, Henry Laurent, Rudolf Wiechert, Helmut Hofmeister
  • Patent number: 4567002
    Abstract: 17-haloethynyl steroids of the partial formula ##STR1## wherein R.sub.1 is hydrogen or methyl,R.sub.2 is alkyl of 1-4 carbon atoms, acyl of 1-7 carbon atoms, trimethylsilyl, 2-tetrahydropyranyl, or nitrate,X is bromine or iodine, andV is methylene, ethylene, vinylene, ethylidene, vinylidene or cyclopropylene,can be prepared by treating an ethynyl steroid of the partial formula ##STR2## wherein R.sub.1, R.sub.2, and V are as defined above, in an inert solvent with a brominating agent or an iodinating agent in the presence of a silver salt. Certain new compounds are also provided.
    Type: Grant
    Filed: April 25, 1984
    Date of Patent: January 28, 1986
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Hofmeister, Henry Laurent, Klaus Annen, Rudolf Wiechert
  • Patent number: 4555507
    Abstract: Compounds of Formula I ##STR1## wherein the bond is a single bond or a double bond,X is hydrogen, flourine, chlorine, or bromine,R.sub.1 is formyl, alkanoyl or alkoxyalkyl each of which contains 2-8 carbon atoms, or benzoyl, andY is chlorine, hydroxy, formyl, alkanoyloxy of 2-8 carbon atoms, or benzoyloxy,have valuable anti-inflammatory properties.
    Type: Grant
    Filed: July 19, 1983
    Date of Patent: November 26, 1985
    Assignee: Schering Aktiengesellschaft
    Inventors: Klaus Annen, Henry Laurent, Helmut Hofmeister, Rudolf Wiechert, Michael Toepert, Hans Wendt
  • Patent number: 4550100
    Abstract: A process for preparing bromine- or iodine-unlabeled or radioactively labeled 17.alpha.-bromoethynyl- and 17.alpha.-iodoethynyl-17.beta.-hydroxy steroids of the androstane and estrane series of the partial formula ##STR1## wherein is a single bond or a double bond,V is a carbon-carbon bond or a methylene group,R is hydrogen or methyl, andX is bromine or iodine,from corresponding 17.alpha.-ethynyl-17.beta.-hydroxy steroids, comprises treating the starting steroid in an inert solvent with a brominating agent or an iodinating agent in the presence of a silver salt.The process enables production of old and new compounds having value as pharmacologically active compounds and also as diagnostic agents when the iodine or bromine is radioactive.
    Type: Grant
    Filed: November 16, 1983
    Date of Patent: October 29, 1985
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Hofmeister, Paul E. Schulze, Klaus Annen, Henry Laurent, Rudolf Wiechert
  • Patent number: 4536401
    Abstract: Compounds of the formula I ##STR1## wherein R.sub.1 is ##STR2## wherein R.sup.I and R.sup.II each independently is alkyl of 1-4 carbon atoms, or R.sup.I and R.sup.II together with the connecting N-atom form a 5- or 6-membered heterocyclic ring whose remaining atoms are all C-atoms, or which also includes and additional N-atom, an additional O or S atom or a combination thereof; ##STR3## wherein R.sup.I and R.sup.II are as defined above; --SR.sup.III, wherein R.sup.III is methyl, ethyl or phenyl; or--OR.sup.IV, wherein R.sup.IV is methyl, ethyl, propyl, methoxymethyl, allyl, or .beta.-dimethylaminoethyl;R.sub.2 is hydrogen, methyl, or ethyl; ##STR4## wherein the wavy lines mean that the substituent is in the .alpha.- or .beta.-position, and ##STR5## M is Na, K or Li; and R.sup.V, R.sup.VI, R.sup.VII and R.sup.VIII each independently is alkyl of 1-4 carbon atoms, have valuable pharmacological properties, e.g., a combination of antiprogestational and antimineralocorticordal effects.
    Type: Grant
    Filed: February 21, 1984
    Date of Patent: August 20, 1985
    Assignee: Schering Aktiengesellschaft
    Inventors: Guenter Neef, Gerhard Sauer, Rudolf Wiechert, Helmut Hofmeister, Ralph Rohde, Klaus Annen, Henry Laurent, Sybille Beier, Wolfgang Losert, Walter Elger, David Henderson
  • Patent number: 4464365
    Abstract: 11.beta.-Chloro-.DELTA..sup.15 -steroids of Formula I ##STR1## wherein R.sup.1 is hydrogen or acyl andR.sup.2 is ethynyl, chloroethynyl, or propynyl have strong progestational activity.
    Type: Grant
    Filed: April 18, 1983
    Date of Patent: August 7, 1984
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Hofmeister, Karl Petzoldt, Klaus Annen, Henry Laurent, Rudolf Wiechert, Yukeshige Nishino
  • Patent number: 4440684
    Abstract: A process for preparing 6-methyl-.DELTA..sup.4,6 -3-keto steroids of the formula ##STR1## comprises reacting a corresponding .DELTA..sup.4 -3-keto steroid with methoxymethyl acetate (CH.sub.3 --O--CH.sub.2 --OAc) in an inert solvent at temperatures above room temperature in the presence of an alkali metal acetate.
    Type: Grant
    Filed: February 4, 1983
    Date of Patent: April 3, 1984
    Assignee: Schering Aktiengesellschaft
    Inventors: Klaus Annen, Henry Laurent, Helmut Hofmeister, Rudolf Wiechert
  • Patent number: 4435390
    Abstract: Hydrocortisone derivatives of Formula I ##STR1## wherein is a single bond or a double bond,n is 1 or 2,R.sub.1 is hydrogen or methyl,R.sub.2 is alkyl of 1-6 carbon atoms, andR.sub.3 is hydrogen or 1-oxoalkyl (alkanoyl) of 2-6 carbon atoms,are pharmacologically active compounds, e.g., as antiinflammatories.
    Type: Grant
    Filed: August 18, 1982
    Date of Patent: March 6, 1984
    Assignee: Schering Aktiengesellschaft
    Inventors: Klaus Annen, Henry Laurent, Helmut Hofmeister, Rudolf Wiechert