Patents Represented by Attorney Charles A. Wendel
  • Patent number: 4158058
    Abstract: The invention relates to novel dibenzo[1,2;5,6]cyclohepta pyridine or -pyrrole derivatives, dibenzo[2,3;6,7]oxepino pyridine or pyrrole derivatives, dibenzo[2,3;6,7]thiepino pyridine or pyrrole derivatives and dibenzo[b,f]pyrido or pyrrolo azepine derivatives of general formula: ##STR1## as well as the pharmaceutically acceptable salts and nitrogen oxides thereof, whereinR.sub.1, r.sub.2, r.sub.3 and R.sub.4 each represent hydrogen, hydroxy, halogen, an alkyl (1-6 C) group, an alkoxy or alkylthio group in which the alkyl group contains 1-6 C-atoms, or a trifluoromethyl group,R.sub.5 represents hydrogen, an alkyl group with 1-6 carbon atoms or an aralkyl group with 7-10 carbon atoms,M is the number 1 or 2,X represents oxygen, sulphur, the group ##STR2## OR THE GROUP --CH.sub.2 -- and R.sub.6 represents hydrogen or a lower alkyl group (1-4 C),having CNS-depressant activity and excellent antihistamine and antiserotonin activities.
    Type: Grant
    Filed: June 26, 1978
    Date of Patent: June 12, 1979
    Assignee: Akzona Incorporated
    Inventor: Willem J. van der Burg
  • Patent number: 4158059
    Abstract: The invention relates to novel dibenzo[1,2;5,6] cyclohepta pyridine or -pyrrole derivatives, dibenzo[2,3;6,7] oxepino pyridine or pyrrole derivatives, dibenzo[2,3;6,7] thiepino pyridine or pyrrole derivatives and dibenzo[b,f] pyrido or pyrrolo azepine derivatives of general formula: ##STR1## as well as the pharmaceutically acceptable salts and nitrogen oxides thereof, whereinR.sub.1, r.sub.2, r.sub.3 and R.sub.4 each represent hydrogen, hydroxy, halogen, an alkyl (1-6 C) group, an alkoxy or alkylthio group in which the alkyl group contains 1-6 C-atoms, or a trifluoromethyl group,R.sub.5 represents hydrogen, an alkyl group with 1-6 carbon atoms or an aralkyl group with 7-10 carbon atoms,M is the number 1 or 2,X represents oxygen, sulphur, the group ##STR2## or the group --CH.sub.2 -- and R.sub.6 represents hydrogen or a lower alkyl group (1-4 C),having CNS-depressant activity and excellent antihistamine and antiserotonin activities.
    Type: Grant
    Filed: June 23, 1978
    Date of Patent: June 12, 1979
    Assignee: Akzona Incorporated
    Inventor: Willem J. van der Burg
  • Patent number: 4156694
    Abstract: The present invention relates to novel benzo(b) bicyclo[3.3.1]nones of the general formula I: ##STR1## and a salt or nitrogen oxide thereof, in which R.sub.1 and R.sub.2 stand for hydrogen, alkyl of 1-6 carbon atoms, alkenyl of 1-6 carbon atoms, an optionally substituted aralkyl group or an acyl group orR.sub.1 and R.sub.2 together with the nitrogen atom represent a heterocyclic 5- or 6-membered ringR.sub.3 is a free, etherified or esterified hydroxy,X and Y stand for hydrogen, hydroxy, halogen, alkyl or alkoxy of 1-6 C-atoms, nitro, CF.sub.3 or an acyloxy group, having valuable biological activities, particularly anorectic activity.
    Type: Grant
    Filed: December 30, 1977
    Date of Patent: May 29, 1979
    Assignee: Akzona Incorporated
    Inventors: Colin L. Hewett, David S. Savage, James Redpath, Thomas Sleigh, Duncan R. Rae
  • Patent number: 4154836
    Abstract: The invention relates to novel dibenzo[1,2;5,6]cyclohepta pyridine or -pyrrole derivatives, dibenzo[2,3;6,7]oxepino pyridine or pyrrole derivatives, dibenzo[2,3;6,7]thiepino pyridine or pyrrole derivatives and dibenzo[b,f]pyrido or pyrrolo azepine derivatives of general formula: ##STR1## as well as the pharmaceutically acceptable salts and nitrogen oxides thereof, whereinR.sub.1, r.sub.2, r.sub.3 and R.sub.4 each represent hydrogen, hydroxy, halogen, an alkyl (1-6 C) group, an alkoxy or alkylthio group in which the alkyl group contains 1-6 C-atoms, or a trifluoromethyl group,R.sub.5 represents hydrogen, an alkyl group with 1-6 carbon atoms or an aralkyl group with 7-10 carbon atoms,M is the number 1 or 2,X represents oxygen, sulphur, the group ##STR2## or the group --CH.sub.2 -- and R.sub.6 represents hydrogen or a lower alkyl group (1-4 C),having CNS-depressant activity and excellent antihistamine and antiserotonin activities.
    Type: Grant
    Filed: June 23, 1978
    Date of Patent: May 15, 1979
    Assignee: Akzona Incorporated
    Inventor: Willem J. van der Burg
  • Patent number: 4154820
    Abstract: A new and remarkably stable synthesized conjugated estrogen composition comprising one or more selected alkali metal synthetic conjugated estrogen sulfate salts and an effective amount of one or more suitable antioxidants has been found for use in novel and stable therapeutic preparations of a pH of not less than about 7 which are adapted to relieve, inter alia, complaints occurring in the menopausal syndrome and other female complaints. Preferably, the steroids are selected from the sodium and potassium salts of the group consisting of estrone, equilin, 17.alpha.-dihydroequilin, and mixtures or conjugates thereof. Most preferably, the preparations are so formulated so that sodium estrone sulfate, sodium equilin sulphate, and 17.alpha.-dihydroequilin sodium sulphate as conjugated estrogens are present in a weight ratio of about 6:3:1, respectively and administered in tablets containing 0.625 mg, 1.25 mg, or 2.5 mg of total conjugated estrogens.
    Type: Grant
    Filed: September 26, 1977
    Date of Patent: May 15, 1979
    Assignee: Akzona Incorporated
    Inventor: Johan R. A. Simoons
  • Patent number: 4152411
    Abstract: A new diagnostic labeled spine tool is disclosed for use in immunoassay techniques, e.g., determination of a component of the antigen-antibody reaction. The new tool is a labeled-spine material product of the formula ##STR1## where R is an organic group labeled with a radioisotope, fluorescent group, lysis-initiating compound, enzyme, or other suitable marker material; T.sub.1 and T.sub.2 are any of --CH.sub.3, ##STR2## --CH.sub.2 OH, --Ch.sub.2 SH, and --NH.sub.2 ; X is selected from the group consisting of (CH.sub.2).sub.m, where m is an integer from 0 to about 10, phenylene, hydroxyl-substituted phenylene, halogen-substituted phenylene, alkyl substituted phenylene or aminated phenylene groups;A is 0, 1 or 2;B is 2-a, with the proviso that there be at least two R groups in the product; andN is a number from 1 to about 100,000The new tool provides higher specific activity for labeled substances thus facilitating determination of the desired compound.
    Type: Grant
    Filed: July 27, 1977
    Date of Patent: May 1, 1979
    Assignee: Akzona Incorporated
    Inventor: Roy F. Schall, Jr.
  • Patent number: 4147783
    Abstract: The invention relates to an oral pharmaceutical preparation with androgenic activity on the basis of one or more esters of testosterone and/or 5.alpha.-dihydrotestosterone, the ester group of which has been derived exclusively from aliphatic carboxylic acids having 9-16 carbon atoms, preferably 10-12 carbon atoms in combination with a non-steroidal lipoid. The preparation may additionally contain a progestational steroid, an oestrogen or a precursor of an A-aromatic steroid.
    Type: Grant
    Filed: November 10, 1977
    Date of Patent: April 3, 1979
    Assignee: Akzona Incorporated
    Inventor: Johannes van der Vies
  • Patent number: 4145434
    Abstract: The invention relates to novel dibenzo?1,2;5,6! cyclophepta pyridine or -pyrrole derivatives, dibenzo?2,3;6,7! oxepino pyridine or pyrrole derivatives, dibenzo?2,3;6,7! thiepino pyridine or pyrrole derivatives and dibenzo?b,f! pyrido or pyrrole azepine derivatives of general formula: ##STR1## as well as the pharmaceutically acceptable salts and nitrogen oxides thereof, whereinR.sub.1, r.sub.2, r.sub.3 and R.sub.4 each represent hydrogen, hydroxy, halogen, an alkyl (1-6 C) group, an alkoxy or alkylthio group in which the alkyl group contains 1-6 C-atoms, or a trifluoromethyl group,R.sub.5 represents hydrogen, an alkyl group with 1-6 carbon atoms or an aralkyl group with 7-10 carbon atoms,M is the number 1 or 2,X represents oxygen, sulphur, the group ##STR2## or the group --CH.sub.2 -- and R.sub.6 represents hydrogen or a lower alkyl group (1-4 C), having CNS-depressant activity and excellent antihistamine and antiserotonin activities.
    Type: Grant
    Filed: May 18, 1977
    Date of Patent: March 20, 1979
    Assignee: Akzona Incorporated
    Inventor: Willem J. VAN DER Burg
  • Patent number: 4143136
    Abstract: A three-phase method of human female contraception wherein (1) starting on about the ninth to about the twelfth day of the female cycle (first cycle day being first menstruation day) an effective amount of at least one progestagenic substance is administered in daily or shorter intervals for about three to about six days followed at substantially similar intervals by (2) administration for about one to about three days starting from about the fourth to about the seventh day after the first phase of both an effective amount of the progestagenic substance(s), and a peptide possessing LHRF (Luteinizing Hormone Release Factor) activity, followed by (3) administration of an effective amount of the progestagenic substance(s) until the total time of the progestagenic substance administration with and without the LHRF compound is from about seven to about fifteen days.
    Type: Grant
    Filed: November 17, 1977
    Date of Patent: March 6, 1979
    Assignee: Akzona Incorporated
    Inventors: Evert De Jage, Jacob De Visser
  • Patent number: 4125718
    Abstract: The invention discloses novel compounds of the general formula: ##STR1## and salts thereof, in which X stands for oxygen, sulphur, the group >NR.sub.7 or the group --CR.sub.8 R.sub.9 --;R.sub.1, r.sub.2, r.sub.3 and R.sub.4 represent hydrogen, hydroxy, halogen, alkyl (1-6 C), alkoxy (1-6 C), alkylthio (1-6 C) or trifluoromethyl;R.sub.5 and R.sub.6 represent hydrogen, alkyl (1-6 C), aralkyl (7-10 C) or together in combination with the nitrogen atom a heterocyclic five- or six-membered ring;R.sub.7 stands for hydrogen or alkyl (1-4 C);R.sub.8 and R.sub.9 stand for hydrogen or methyl,n is the number 0, 1 or 2 andThe dotted line means an optional C--C bond,With valuable central nervous system (CNS) activities, especially antidepressant activity.
    Type: Grant
    Filed: November 15, 1977
    Date of Patent: November 14, 1978
    Assignee: Akzona Incorporated
    Inventor: Willem J. van der Burg
  • Patent number: 4110322
    Abstract: Biologically active novel peptide compounds are disclosed of the formulaA-L-B-D-Lys-L-Phe-Gly-(L or D)Lys-L-Pro-L-Val-Gly-L-Lys-L-Lys-Xor a pharmaceutically acceptable non-toxic functional derivative thereof; A is a N-terminal chain prolongation selected from the group consisting of (1) hydrogen and (2) N-acyl radicals derived from (a) alkyl carboxylic acids having from one to about six carbons, (b) aralkyl carboxylic acids having from seven to about ten carbons, (c) amino acids, (d) peptides, (e) the N-alkylcarbonyl or N-aralkylcarbonyl derivatives of the amino acids, and (f) the N-alkylcarbonyl or N-aralkylcarbonyl derivatives of the peptides; B is an amino-acid residue selected from the group consisting of Phe, Trp, Tyr, and --NH--CHR.sub.1 --CO--, wherein R.sub.1 is hydrogen or alkyl from one to about six carbons; and X is a member selected from the group consisting of hydroxy, esterified hydroxy radicals, unsubstituted amino radicals and substituted amino radicals.
    Type: Grant
    Filed: June 27, 1977
    Date of Patent: August 29, 1978
    Assignee: Akzona Incorporated
    Inventors: Hendrik M. Greven, David DE Wied
  • Patent number: 4107206
    Abstract: The present invention relates to novel biologically active tricyclic compounds of the general formula: ##STR1## and salts thereof, IN WHICHR.sub.1 and R.sub.2 stand for hydroge, alkyl or alkenyl, an optionally substituted aralkyl group or an acyl group orR.sub.1 + r.sub.2 together with the nitrogen atom represent a heterocyclic 5- or 6-membered ring, andX and Y stand for hydrogen, hydroxy, halogen, alkyl or alkoxy of 1-6 carbon atoms, nitro, trifluoromethyl or an acyloxy group,Which compounds have valuable biological activities, particularly anorectic activity.
    Type: Grant
    Filed: October 26, 1976
    Date of Patent: August 15, 1978
    Assignee: Akzona Incorporated
    Inventors: Colin Leslie Hewett, David Samuel Savage
  • Patent number: 4104371
    Abstract: Biologically active novel peptides and peptide-derivatives of the general formula: ##STR1## where A represents H-(L or D)Met, H-(L or D)Met(.fwdarw.O), H-(L or D)Met(.fwdarw.O.sub.2)desamino-Met, desamino-Met(.fwdarw.O),desamino-Met(.fwdarw.O.sub.2) or the group H.sub.2 N--B--CO--;B represents a branched or straight-chain alkylene (C.sub.1 -C.sub.6) or alkylidene (C.sub.1 -C.sub.6) group;Q represents the amino-acid residue --NH--CHR--CO--;R represents alkyl (C.sub.1 -C.sub.6), p-hydroxyphenylmethyl, 3-indolylmethyl or phenylmethyl;R.sub.1 and R.sub.2 represent hydrogen or an alkyl(1-6C) group, andZ represents N-(phenylalkyl)amino, N-(.beta.-indolylalkyl)amino, L-Trp-OH, L-Phe-OH, L-Trp-Gly-OH or L-Phe-Gly-OH, as well as the functional derivatives thereof.
    Type: Grant
    Filed: June 30, 1977
    Date of Patent: August 1, 1978
    Assignee: Akzona Incorporated
    Inventors: Hendrik Marie Greven, David DE Wied
  • Patent number: 4101675
    Abstract: The invention relates to compounds of the general formula: ##STR1## in which one double bond is present between the carbon atom of the quanidine moiety and one of the adjacent nitrogen atoms andR.sub.0 stands for hydrogen, halogen, hydroxy, alkoxy or alkyl (1 to 6 C),R.sub.1, r.sub.2 for halogen, hydroxy, alkyl (1 to 4 C) or alkoxy (1 to 4 C),R.sub.3, r.sub.3 ', r.sub.3 " for hydrogen or alkyl (1 to 4 C), on the understanding that one of the substituents R.sub.3, R.sub.3 ' or R.sub.3 " is absent because of the presence of the double bond,R.sub.4 for hydrogen, alkyl (1-4 C), hydroxy, alkoxy (1-4 C) or amino optionally substituted with one or two alkyl (1 to 4 C) groups,R.sub.5, r.sub.6 for hydrogen, alkyl (1-6 C), acyl or R.sub.5 + R.sub.6 together represent an alkylidene, cyclic alkylidene or aralkylidene group, as well as the acid addition salts thereof,Provided that, if R.sub.4 stands for methyl and R.sub.0, R.sub.3, R.sub.3 ", R.sub.5 and R.sub.6 for hydrogen, R.sub.1 and R.sub.
    Type: Grant
    Filed: January 29, 1976
    Date of Patent: July 18, 1978
    Assignee: Akzona Incorporated
    Inventor: Harm Jan Panneman
  • Patent number: 4098802
    Abstract: The invention relates to an oral pharmaceutical preparation with androgenic activity on the basis of one or more esters of testosterone and/or 5.alpha.-dihydrotestosterone, the ester group of which has been derived exclusively from aliphatic carboxylic acids having 9-16 carbon atoms, preferably 10-12 carbon atoms in combination with a non-steroidal lipoid. The preparation may additionally contain a progestational steroid, an oestrogen or a precursor of an A-aromatic steroid.
    Type: Grant
    Filed: May 28, 1976
    Date of Patent: July 4, 1978
    Assignee: Akzona Incorporated
    Inventor: Johannes van der Vies
  • Patent number: 4097338
    Abstract: The present invention relates to a rapid and sensitive method for the determination of a reduced coenzyme, particularly NADH, NADPH and derivatives thereof, in that the fluorescence of such a reduced coenzyme in an aqueous medium is measured in the presence simultaneously of an organic liquid miscible with water and a dipersion of one or more slightly soluble or insoluble substances.
    Type: Grant
    Filed: January 21, 1976
    Date of Patent: June 27, 1978
    Assignee: Akzona Incorporated
    Inventors: Aarne Ilmari Konttinen, Bastiaan Cornelis Goverde, Peter Silvester Lambertus Janssen
  • Patent number: 4076726
    Abstract: The invention relates to novel amidino-hydrazone derivatives of the general formula: ##STR1## in which the dotted lines mean one extra bond starting from the (guanidine-) carbon atom to one of the adjacent nitrogen atoms, andA stands for methylene, ethylene, propylene or butylene, which groups may optionally be substituted with alkyl (1-4 C),R stands for hydroxy, alkyl (1-4 C), alkylthio or alkoxy (1-4 C), halogen, trifluoromethyl, nitro, amino, hydroxymethyl, acyloxy or an alkylenedioxy group,N is the number 0, 1, 2, 3 or 4,R.sub.1, r.sub.4 and R.sub.5 represent hydrogen or alkyl (1-4 C), with the proviso that one of them is absent in view of the presence of the double bond,R.sub.2 and R.sub.3 stand for hydrogen, alkyl (1-4 C), aralkyl, aryl, hydroxy or amino, with the proviso thatR.sub.2 + r.sub.3 together may also represent a saturated or unsaturated alkylene group with 2 or 3 carbon atoms, orR.sub.3 + r.sub.
    Type: Grant
    Filed: May 21, 1975
    Date of Patent: February 28, 1978
    Assignee: Akzona Incorporated
    Inventors: Harm Jan Panneman, Antonius Hermanus Nicolaas Maria Bruins
  • Patent number: 4071623
    Abstract: The invention relates to a novel pharmaceutical preparation with oestrogenic activity adapted for oral administration comprising an oestradiol-17.beta.-ester, the ester group of which has been derived from aliphatic carboxylic acids having 9-16 carbon atoms, in combination with a non-steroidal lipoid. The preparation may additionally contain a progestational steroid or an androgen. The invention also relates to novel oestradiol-17.beta.-esters.
    Type: Grant
    Filed: May 17, 1976
    Date of Patent: January 31, 1978
    Assignee: Akzona Incorporated
    Inventor: Johannes van der Vies
  • Patent number: 4066744
    Abstract: Disclosed are a reagent and test slide used for serological detection of gonorrheal antibodies in human blood serum or synovial fluid. The reagent comprises latex particles having absorbed on their surfaces an inert protein, such as bovine serum albumin and a heat labile antigen derived from Neisseria gonorrhoeae bacteria exhibiting T.sub.1 colonial morphology. The reagent may be employed by several forms, for example, as a liquid suspension of the latex particles, or in the form of a dried deposit of the latex particles. Regardless of the form employed, the reagent is particularly useful as a routine screening test in hospitals and prenatal clinics to detect gonococcal infection in women and also in cases of complicated gonorrhea, e.g., gonorrheal arthritis where infection is not conveniently detectable by present means. The test slide may have dried thereon an absorbing antigen for heterophile antibodies.
    Type: Grant
    Filed: January 16, 1976
    Date of Patent: January 3, 1978
    Assignee: Akzona Incorporated
    Inventors: Richard T. Price, Rita C. Prodell
  • Patent number: 4062848
    Abstract: The invention relates to compounds of the general formula I: ##STR1## or a salt thereof, in which A represents a pyridine ring or a halogen substituted pyridine ring,R.sub.1 represents hydrogen, alkyl (1-6 C), alkoxy (1-6 C), alkylthio (1-6 C), halogen, OH, SH or CF.sub.3R.sub.2 represents hydrogen or a lower alkyl or aralkyl group andn and m may each be 1, 2 or 3 with the proviso that the sum of m and n must be 2, 3 or 4, having CNS activity, a pronounced antihistamine activity and little or no antiserotonin activity.
    Type: Grant
    Filed: March 23, 1976
    Date of Patent: December 13, 1977
    Assignee: Akzona Incorporated
    Inventor: Willem Jacob van der Burg