Patents by Inventor Henry Laurent

Henry Laurent 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).

  • Patent number: 4673673
    Abstract: 17.alpha.-Alkyl-17.beta.-hydroxy-1.alpha.-methyl-4-androsten-3-ones of the formula ##STR1## wherein R is a straight-chain alkyl residue of 3-8 carbon atoms, i.e., C.sub.3-8 -n-alkyl, are pharmacologically active compounds distinguished by antiandrogenic activity, especially upon topical application.
    Type: Grant
    Filed: August 6, 1985
    Date of Patent: June 16, 1987
    Assignee: Schering Aktiengesellschaft
    Inventors: Henry Laurent, Rudolf Wiechert
  • 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: 4614616
    Abstract: A process for preparing a 3.beta.,7.beta.-dihydroxy-.DELTA..sup.5 -steroid of the formula ##STR1## wherein Q is ##STR2## and R.sub.1 is hydrogen, trimethylacetyl, tert-butyldimethylsilyl, dimethyl-2-(3-methylbutyl)silyl or tribenzylsilyl, comprises fermenting a 3.beta.-hydroxy-.DELTA..sup.5 -steroid of the formula ##STR3## wherein Q is as defined above, andR.sub.2 is hydrogen or alkanoyl of 2-6 carbon atoms, with a culture of Botryodiplodia malorum to obtain the corresponding 3.beta.,7.beta.-dihydroxy-.DELTA..sup.5 -steroid; and, optionally, reacting the resultant product with trimethylacetic anhydride, tert-butyldimethylsilyl chloride, dimethyl-2-(3-methylbutyl)silyl chloride, or tribenzylsilyl chloride.
    Type: Grant
    Filed: September 26, 1983
    Date of Patent: September 30, 1986
    Assignee: Schering Aktiengesellschaft
    Inventors: Karl Petzoldt, Rudolf Wiechert, Henry Laurent, Klaus Nickisch, Dieter Bittler
  • 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: 4587235
    Abstract: Androstane derivatives of Formula I ##STR1## wherein is a single bond or a double bond,R.sub.1 is methyl or ethyl,R.sub.2 is hydrogen or alkyl of 1-8 carbon atoms,--X-- is --(CH.sub.2).sub.n --, --CH.dbd.CH(CH.sub.2).sub.m --, or --C.tbd.C--(CH.sub.2).sub.m -- wherein n is 2 to 6 and m is 1 to 4,--A--B-- is --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH--, --CCl.dbd.CH--, ##STR2## --U--V< is --CH.sub.2 --CH<, --CH.dbd.C<, --C(OH).dbd.C<, or --CCl.dbd.C<, and--W--Y-- is --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --C(CH.sub.3).sub.2 --, or ##STR3## with the proviso that the compound is not 17.alpha.-(3-acetoxypropyl)-17.beta.-hydroxy-4,6-androstadien-3-one, are pharmacologically efficacious compounds, e.g., are sebum suppressive.
    Type: Grant
    Filed: June 27, 1984
    Date of Patent: May 6, 1986
    Assignee: Schering Aktiengesellschaft
    Inventors: Dieter Bittler, Henry Laurent, Klaus Nickisch, Rudolf Wiechert
  • Patent number: 4584288
    Abstract: 6,6-ethylene-15,16-methylene-3-oxo-17.alpha.-pregn-4-ene-21,17.alpha.-carbo lactones of general Formula I ##STR1## wherein ##STR2## is a CC-single of CC-double bond, R.sub.1 is a hydrogen atom or a methyl group,R.sub.2 is a methyl or ethyl group, and ##STR3## exhibit strong gestagen potency and an aldosterone-antagonistic activity.
    Type: Grant
    Filed: January 18, 1985
    Date of Patent: April 22, 1986
    Assignee: Schering Aktiengesellschaft
    Inventors: Klaus Nickish, Dieter Bittler, Henry Laurent, Rudolf Wiechert, Sybille Beier, Walter Elger
  • 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: 4559331
    Abstract: Novel 7.alpha.-substituted 3-oxo-17.alpha.-pregn-4-ene-21,17-carbolactones of the formula ##STR1## wherein ##STR2## is a CC single or CC double bond or the group ##STR3## R.sup.7 is the group SR', R' being a hydrogen atom or a straight-chain or branched alkyl residue of 1-6 carbon atoms optionally substituted by a hydroxy or acyloxy group, the group COOR" or the group COR" wherein R" is an alkyl group of 1-4 carbon atoms and ##STR4## is a CC single bond or the group ##STR5## have antialdosterone activity with reduced endocrinological side effects.
    Type: Grant
    Filed: August 17, 1984
    Date of Patent: December 17, 1985
    Assignee: Schering Aktiengesellschaft
    Inventors: Klaus Nickisch, Henry Laurent, Peter Esperling, Dieter Bittler, Rudolf Wiechert, Wolfgang Losert
  • 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: 4542128
    Abstract: 17.alpha.-Pregn-4-ene-3-oxo-21-carboxylic acid esters of Formula I ##STR1## wherein C.sub.1 C.sub.2 is a CC single or C.dbd.C double bond,--A--B--is ##STR2## --C--D--is ##STR3## and R is an alkyl or alkenyl residue of up to 6 carbon atoms,in addition to antialdosterone activity, exhibit greatly reduced antiandrogenic and progestational side effects.
    Type: Grant
    Filed: July 22, 1983
    Date of Patent: September 17, 1985
    Assignee: Schering Aktiengesellschaft
    Inventors: Dieter Bittler, Henry Laurent, Klaus Nickisch, Rudolf Weichert, Jorge Casals-Stenzel
  • Patent number: 4542024
    Abstract: New 15,16-methylene-17.alpha.-pregna-4,6-diene-21-carboxylic acid salts of formula I ##STR1## wherein R.sup.1 and R.sup.2 each alone is hydrogen or together they form an additional CC bond or a methylene group,M is an alkali metal,and the methylene group in the 15,16 position is in the .alpha. or .beta. position, in addition to having a strong antialdosterone effect, have reduced antiandrogenic and progestogenic side effects.
    Type: Grant
    Filed: July 13, 1984
    Date of Patent: September 17, 1985
    Assignee: Schering Aktiengesellschaft
    Inventors: Klaus Nickisch, Dieter Bittler, Henry Laurent, Rudolf Wiechert, Wolfgang Losert
  • 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: 4511565
    Abstract: 7.alpha.-acylthio-1.alpha.,2.alpha.-methylene-3-oxo-17.alpha.-pregn-4-ene-2 1,17-carbolactones of Formula I ##STR1## wherein ##STR2## and R is a lower saturated acyl radical of 2 to 4 carbon atoms,have a stronger antialdosterone effect and lower side effects than spironoloctone.
    Type: Grant
    Filed: October 28, 1983
    Date of Patent: April 16, 1985
    Assignee: Schering Aktiengesellschaft
    Inventors: Henry Laurent, Klaus Nickisch, Dieter Bittler, Rudolf Wiechert, Wolfgang Losert
  • Patent number: 4500522
    Abstract: 7.alpha.-acylthio-15,16-methylene-3-oxo-17.alpha.-pregna-1,4-diene-21,17-ca rbolactones of the formula ##STR1## wherein the 15,16-methylene group can be in the .alpha.- or .beta.-configuration, andR is a lower alkyl residue,have altialdosterone activity.They are prepared from corresponding .DELTA..sup.4 -unsaturated compounds by chemical or microbiological 1,2-dehydrogenation.
    Type: Grant
    Filed: July 22, 1983
    Date of Patent: February 19, 1985
    Assignee: Schering Aktiengesellschaft
    Inventors: Klaus Nickisch, Dieter Bittler, Henry Laurent, Rudolf Wiechert, Wolfgang Losert
  • Patent number: 4472310
    Abstract: The disclosure concerns 5.beta.-hydroxy-.DELTA..sup.6 -steroids of the general formula ##STR1## wherein R.sup.1 is hydrogen, acyl, lower alkyl, or the tetrahydropyranyl residue andR.sup.2, R.sup.3 individually are respectively hydrogen or jointly are methylene andX stands for oxygen, the groupings ##STR2## (wherein R.sup.4 means hydrogen or acyl) and ##STR3## (wherein R.sup.5 means hydrogen or lower alkyl) and a process for the preparation thereof by reacting corresponding 7.alpha.-chloro-5.beta.,6.beta.-epoxy steroids in an inert solvent with metallic zinc in a lower aliphatic carboxylic acid or dilute mineral acid at temperatures of between room temperature and 100.degree. C., preferably at 40.degree.-70.degree. C.The compounds producible by this method are intermediates for the preparation of 3-keto-.DELTA..sup.4 -6.beta.,7.beta.-methylene steroids constituting pharmacologically valuable compounds, for example aldosterone antagonists.
    Type: Grant
    Filed: March 11, 1982
    Date of Patent: September 18, 1984
    Assignee: Schering Aktiengesellschaft
    Inventors: Dieter Bittler, Henry Laurent, Klaus Nickisch, Robert Nickolson, Rudolf Wiechert
  • Patent number: 4464364
    Abstract: Novel 6.beta.,7.beta.-methylene-17.alpha.-pregn-4-ene-21,17-carbolactones of Formula I ##STR1## wherein R and R' each is hydrogen or jointly form a methylene group.These exhibit a good antimineralocorticoid effect with low side effects.
    Type: Grant
    Filed: June 9, 1983
    Date of Patent: August 7, 1984
    Assignee: Schering Aktiengesellschaft
    Inventors: Dieter Bittler, Henry Laurent, Rudolf Weichert, Jorge Casals-Stenzel, Ekkehard Schillinger
  • 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