Patents Assigned to Endo Laboratories, Inc.
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Patent number: 4254134Abstract: 2-Amino- and 2-(substituted amino)-tetrahydro- and -cis-hexahydro-carbazoles useful for alleviating depression in mammals or as intermediate compounds thereto.Type: GrantFiled: March 17, 1978Date of Patent: March 3, 1981Assignee: Endo Laboratories, Inc.Inventor: Leonard J. Fliedner, Jr.
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Patent number: 4238607Abstract: The compounds are prepared by cyclizing compounds of formula II ##STR2## wherein R.sup.2 is R.sup.1 or acyl.Type: GrantFiled: July 9, 1979Date of Patent: December 9, 1980Assignee: Endo Laboratories Inc.Inventor: Parathasarathi Rajagopalan
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Patent number: 4217454Abstract: Process for the stereoselective reduction of certain amino-substituted indoles and amino-substituted indole-containing structures to trans-dihydroindoles comprising the sequential steps of (1) reacting a strong acid addition salt of such an indole with a borohydride in an appropriate solvent in the absence of acid, and (2) acidifying the step (1) reaction product by which it is reduced and hydrolyzed to form the corresponding trans-dihydroindole. Many dihydroindoles so produced, for example, the trans-2-(adamantylemethyl)-=2,3,4,4a,5,9b-hexahydro-5-phenyl-1H-pyrido[4,3 -b]indole, are useful as pharmaceutical materials, such as tranquilizers.Type: GrantFiled: July 26, 1978Date of Patent: August 12, 1980Assignee: Endo Laboratories, Inc.Inventor: Joel G. Berger
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Patent number: 4183936Abstract: The compounds are prepared by cyclizing compounds of formula II ##STR2## wherein R.sup.2 is R.sup.1 or acyl.Type: GrantFiled: June 16, 1978Date of Patent: January 15, 1980Assignee: Endo Laboratories, Inc.Inventor: Parthasarathi Rajagopalan
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Patent number: 4174453Abstract: Certain trans-2,3,4,4a,5,9b-hexahydro-1H-pyrido-[4,3-b]indoles are useful as analgesics and sedatives. Some are also useful as major (antipsychotics) and/or minor (anxiolytics) tranquilizers, muscle relaxants, or hypotensives. The compounds of this invention are made by (1) reaction of .DELTA..sup.4a,9b -tetrahydro precursors with borane/THF and (2) acidifying the reaction product by which it is reduced and hydrolyzed to form the corresponding trans-hexahydro compound.Type: GrantFiled: May 22, 1978Date of Patent: November 13, 1979Assignee: Endo Laboratories, Inc.Inventor: Joel G. Berger
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Patent number: 4141980Abstract: Certain 2-substituted trans-hexahydropyridoindoles are useful as major tranquilizers in warm-blooded animals or are useful as intermediates for producing such major tranquilizers.Type: GrantFiled: December 13, 1977Date of Patent: February 27, 1979Assignee: Endo Laboratories Inc.Inventor: Joel G. Berger
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Patent number: 4115577Abstract: The compounds are prepared by cyclizing compounds of formula II ##STR2## wherein R.sup.2 is R.sup.1 or acyl.Type: GrantFiled: December 28, 1976Date of Patent: September 19, 1978Assignee: Endo Laboratories, Inc.Inventor: Parthasarathi Rajagopalan
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Patent number: 4091102Abstract: Novel trans-hexahydropyrido[3,4-b]indoles and their suitable pharmaceutical salts useful for alleviating depression in mammals.Type: GrantFiled: June 22, 1976Date of Patent: May 23, 1978Assignee: Endo Laboratories, Inc.Inventor: Sonia Ruth Teller
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Patent number: 4070467Abstract: Certain 3-substituted trans-octahydro-pyrido-pyrrolo-benzazepines are useful as major tranquilizers in warm-blooded animals or are useful as intermediates for producing such major tranquilizers.Type: GrantFiled: April 8, 1976Date of Patent: January 24, 1978Assignee: Endo Laboratories, Inc.Inventor: Joel G. Berger
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Patent number: 4065453Abstract: The levorotatory enantiomer of molindone [3-ethyl-6,7-dihydro-2-methyl-5-(morpholinomethyl)-indol-4(5H)-one] has been isolated and found to have significantly greater antidepressant activity than the corresponding racemate.Type: GrantFiled: November 1, 1976Date of Patent: December 27, 1977Assignee: Endo Laboratories, Inc.Inventor: Michael Finizio
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Patent number: 4018930Abstract: Certain trans-1,2,3,4,4a,8,9,14a-octahydropyrido-[4',3':2,3]indolo[1,7-ab][1]benza zepines substituted at the 3-position with (a) certain unsaturated organic radicals, prepared by alkylation or acylation/reduction of the corresponding unsubstituted compound or (b) cis-2,3-dimethylcyclopropyl)methyl, prepared by hydrogenation of the corresponding 3-(2,3-dimethylcycloprop-2-en-1-yl)methyl compound. The compounds are useful as analgesics and sedative-tranquilizers.Type: GrantFiled: July 17, 1975Date of Patent: April 19, 1977Assignee: Endo Laboratories, Inc.Inventor: Joel G. Berger
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Patent number: 4013652Abstract: Compounds of the formula: ##STR1## where 2 THE R's are the same or different and are H or CH.sub.3, and one of them can be C.sub.2 -C.sub.9 alkyl or phenyl; R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.2l -C.sub.4 alkoxycarbonyl, or substituted C.sub.1 -C.sub.4 alkyl where the substituent is C.sub.3 -C.sub.6 cycloalkyl or phenyl; and Z is H, Cl or CH.sub.3 ; and their pharmaceutically suitable salts. The compounds are useful as sedatives; some of them also exhibit antidepressant activity.Type: GrantFiled: June 13, 1975Date of Patent: March 22, 1977Assignee: Endo Laboratories, Inc.Inventor: Parthasarathi Rajagopalan
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Patent number: 3991199Abstract: Certain trans-2,3,4,4a,5,9b-hexahydro-1H-pyrido-[4,3-b] indoles useful as analgesics and sedatives. Some are also useful as major (antipsychotics) and/or minor (anxiolytics) tranquilizers, muscle relaxants, or hypotensives. The compounds of this invention are made by borane/THF reduction of .DELTA..sup.4a,9b -tetrahydro precursors, followed where necessary by dealkylation, alkylation and/or acylation/reduction.Type: GrantFiled: November 8, 1974Date of Patent: November 9, 1976Assignee: Endo Laboratories, Inc.Inventor: Joel G. Berger
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Patent number: 3983123Abstract: Certain 3-substituted octahydropyridoindolobenzazepines and their addition salts with pharmaceutically acceptable acids produce a marked central nervous system depressant activity in warm-blooded animals. These compounds are stereoisomers of prior art 3-substituted octahydropyridoindolobenzazepines which have a central nervous system antidepressant activity.Type: GrantFiled: August 7, 1975Date of Patent: September 28, 1976Assignee: Endo Laboratories, Inc.Inventor: Charles De Witt Adams
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Patent number: 3959300Abstract: Certain novel 1,2,3,4,8,9-hexahydro-3-(substituted)pyrido[4',3':2,3]indolo[1,7-ab][1]-be nzazepines are useful as minor tranquilizers (anxiolytics) and/or major tranquilizers (antipsychotics). The minor tranquilizers are effective at non-ataxic doses, and are not likely to cause addiction when abused. A representative compound in this class is 3-(cyclopropylmethyl)-1,2,3,4,8,9-hexahydropyrido[4',3':2,3]indolo[1,7-ab] [1]benzazepine.Type: GrantFiled: June 14, 1974Date of Patent: May 25, 1976Assignee: Endo Laboratories, Inc.Inventor: Michael Finizio