Chalcogen Or Additional Nitrogen Attached Indirectly To Ring Carbon Of The Five-membered Hetero Ring By Acyclic Nonionic Bonding Patents (Class 548/507)
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Patent number: 4803218Abstract: Compounds useful as antihypertensive agents which are 3-aminoalkyl-1H-indole-5-urea or amide derivatives having the following formula: ##STR1## or a pharmaceutically acceptable acid addition salts thereof, wherein: R is C.sub.1-4 loweralkyl, C.sub.1-4 loweralkoxy, phenyl, ##STR2## pyrrolyl, pyridyl or is a substituted nitrogen represented by: ##STR3## wherein R.sub.1 is H or a C.sub.1-4 loweralkyl or phenyl or cycloalkyl; R.sub.2 is H or a C.sub.1-4 loweralkyl; Y is H or halo; R.sub.3 is H or a C.sub.1-4 loweralkyl; R.sub.4 is H or a C.sub.1-4 loweralkyl; R.sub.5 is H or a C.sub.1-4 loweralkyl or carboxymethyl or carboxytrifluoromethyl; R.sub.6 is H or a C.sub.1-4 loweralkyl, and R.sub.5 and R.sub.6 may also be taken together as an N-loweralkyl-pyrrolidinylidene group.Type: GrantFiled: September 29, 1982Date of Patent: February 7, 1989Assignee: McNeilab, Inc.Inventors: Kerry G. Stanley, Winston Ho
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Patent number: 4795757Abstract: Compounds of the formula: ##STR1## and pharmaceutically acceptable salts thereof, wherein: Ar is phenyl, naphthyl, heteroaryl, indole, or fused arylcycloalkyl optionally substituted with hydroxy, halo, CF.sub.3, NO.sub.2, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or aryloxy;A and A' are each hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxy or aryloxy;X is cyano, nitro, COOR, SR, SOR or SOOR;R is H, C.sub.1-6 alkyl or aryl;n n' and n" are each 0 to 4; andm, m' and m" are each 1 to 4, have calcium channel blocking activity.Type: GrantFiled: November 20, 1986Date of Patent: January 3, 1989Assignee: Rorer Pharmaceutical CorporationInventors: John R. Regan, Jeffrey N. Barton, John T. Suh, Jerry W. Skiles
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Patent number: 4774240Abstract: The invention relates to N-indolylethyl-sulphonic acid amides of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are defined in the specification and X is carboxyl, alkoxycarbonyl, cyano or carboxamido. These active compounds are useful in medicaments in combating thromboses, thromboembolisms, allergies or asthmatic disorders.Type: GrantFiled: April 14, 1986Date of Patent: September 27, 1988Assignee: Bayer AktiengesellschaftInventors: Horst Boshagen, Ulrich Rosentreter, Folker Lieb, Hermann Oediger, Friedel Seuter, Elisabeth Perzborn, Volker-Bernd Fiedler
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Patent number: 4772726Abstract: Melatonine is obtained by methylating N-acetyl serotonine in the 5-position. Mexamine is obtained by de-acetylating melatonine in a hot alkaline solution containing a water-insoluble alcohol and acidifying the alcohol phase with hydrochloric acid.Type: GrantFiled: October 31, 1986Date of Patent: September 20, 1988Assignee: Nestec S. A.Inventors: Raymond Bertholet, Pierre Hirsbrunner
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Patent number: 4748252Abstract: Indole derivatives characterized by having a 1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid nucleus bearing a substituent in position 1 and 4. The nucleus may be optionally substituted at position 8. The derivatives are useful anti-inflammatory and analgesic agents and methods and chemical intermediates for their preparation are also disclosed.Type: GrantFiled: January 28, 1987Date of Patent: May 31, 1988Assignee: American Home Products CorporationInventors: Eckhardt S. Ferdinandi, Dominick Mobilio, Joseph P. Sabatucci, Leslie G. Humber
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Patent number: 4740611Abstract: Disclosed are new compounds ##STR1## where each of R and R' have zero to 10 C atoms; R is H or hydrocarbyl; R' is H, hydrocarbyl, or hydrocarbyl substituted with hydrocarbylcarbonylamino, di(hydrocarbylcarbonyl)amino, hydrocarbylcarbonyl(hydrocarbyl)amino, formylamino, diformylamino and formyl(hydrocarbyl)amino, hydrocarbyloxy, hydrocarbylthio, formylthio, hydrocarbylcarbonylthio, hydrocarbyloxycarbonyl, hydrocarbyl carboxyl, hydrocarbylamino, dihydrocarbylamino, formyl, 3-indolyl, 3-(1-hydrocarbyl)indolyl, 3-(1-hydrocarbylcarbonyl)indolyl, 3-(1-formyl)indolyl, carbamoyl, hydrocarbylcarbamoyl, dihydrocarbylcarbamoyl, 5-imidazolyl, 5-(3-hydrocarbyl)imidazolyl, 5-(3-hydrocarbylcarbonyl)imidazolyl, or 5-(3-formyl)imidazolyl, and R" is phenyl or a C.sub.1 to C.sub.6 alkyl group; and methods of making such compounds.Type: GrantFiled: October 30, 1986Date of Patent: April 26, 1988Assignee: The Standard Oil CompanyInventors: Mark C. Cesa, James E. Rinz, Gilles Klopman, Teodora T. Kopp
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Patent number: 4738803Abstract: Derivatives having the general formula: ##STR1## in which the various radicals, A,B,X,R.sub.1, R.sub.2, R.sub.3 and n have indicated definitions. These compounds have in particular enkephalinase-inhibiting, antalgic, antidepressive, antidiarrhea and hypotensive activities.Type: GrantFiled: August 22, 1986Date of Patent: April 19, 1988Inventors: Bernard Roques, Jean-Charles Schwartz, Jeanne-Marie Lecomte
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Patent number: 4672067Abstract: Compounds are disclosed of formula (I) ##STR1## wherein R.sub.1 represents CHO, COR.sub.8, CO.sub.2 R.sub.8, CONR.sub.9 R.sub.10, CSNR.sub.9 R.sub.10 or SO.sub.2 NR.sub.9 R.sub.10, whereR.sub.8 represents alkyl, cycloalkyl, aryl or aralkyl,R.sub.9 represents hydrogen or alkyl, andR.sub.10 represents hydrogen or alkyl, cycloalkyl, aryl or aralkyl;R.sub.2, R.sub.3, R.sub.4, R.sub.6 and R.sub.7 each independently represents hydrogen or C.sub.1-3 alkyl;R.sub.5 represents hydrogen, or alkyl, cycloalkyl, alkenyl or aralkyl, orR.sub.4 and R.sub.5 together form an aralkylidene group or R.sub.4 and R.sub.5 together with the attached nitrogen atom form a saturated monocyclic 5- to 7-membered ring; andAlk represents C.sub.2-3 alkylene chain optionally substituted by not more than two C.sub.1-3 alkyl groups;and physiologically acceptable salts and solvates thereof.Type: GrantFiled: June 28, 1984Date of Patent: June 9, 1987Assignee: Glaxo Group LimitedInventors: Ian H. Coates, Keith Mills, Colin F. Webb, Michael D. Dowle, David E. Bays
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Patent number: 4636521Abstract: Compounds are disclosed of general formula (I) ##STR1## wherein R.sub.1 represents an alkyl, cycloalkyl, aryl or aralkyl group;R.sub.2, R.sub.3, R.sub.4, R.sub.6 and R.sub.7, which may be the same or different, each represents a hydrogen atom or a C.sub.1-3 alkyl group;R.sub.5 represents a hydrogen atom or an alkyl, cycloalkyl, alkenyl or an aralkyl group; or R.sub.4 and R.sub.5 together form an aralkylidene group or R.sub.4 and R.sub.5 together with the nitrogen atom to which they are attached form a saturated monocyclic 5- to 7-membered ring; Alk represents an alkylene chain containing two or three carbon atoms which may be unsubstituted or substituted by not more than two C.sub.1-3 alkyl groups; and physiologically acceptable salts, solvates and bioprecursors thereof. The compounds are described as potentially useful for the treatment of migraine and may be formulated as pharmaceutical compositions in conventional manner using one or more pharmaceutically acceptable carriers or excipients.Type: GrantFiled: June 29, 1984Date of Patent: January 13, 1987Assignee: Glaxo Group LimitedInventors: Ian H. Coates, Keith Mills, Colin F. Webb, Michael D. Dowle, David E. Bays
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Patent number: 4614807Abstract: 6,7-Dichloromelatonin and related compounds are ovulation inhibitors of the formula ##STR1## wherein R and R.sup.1 are individually F or Cl, R.sup.2 is C.sub.1-3 alkyl, including methyl, ethyl, n-propyl and isopropyl, and R.sup.3 is H or methyl.Type: GrantFiled: October 4, 1984Date of Patent: September 30, 1986Assignee: Eli Lilly and CompanyInventor: Michael E. Flaugh
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Patent number: 4582848Abstract: This disclosure relates to substituted indolamines, which exhibit anti-diabetic activity, having the formula: ##STR1## where m is an integer from 1 to 4,x represents hydrogen or --OHR represents Ar or ##STR2## and Ar represents ##STR3## R.sub.1 represents hydrogen, fluoro, chloro, lower alkyl or lower alkoxy, R.sub.2 and R.sub.3 each, independently, represent lower alkyl, orR.sub.2 and R.sub.3 together with N represent ##STR4## wherein n is 1, 2 or 3,R.sub.4 represents hydrogen or lower alkyl, andR.sub.5 represents hydrogen or lower alkyl, unsubstituted phenyl or phenyl substituted with fluoro, chloro, lower alkyl or lower alkoxy, oror pharmaceutically acceptable acid addition salts thereof.Type: GrantFiled: June 16, 1983Date of Patent: April 15, 1986Assignee: Sandoz, Inc.Inventor: Jeffrey Nadelson
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Patent number: 4562201Abstract: The present invention relates to new compounds of the formula ##STR1## where X is ##STR2## alkylene, or --S-- where R.sub.1 is hydrogen, alkyl, or aryl; W is hydrogen, hydroxy, amino, alkyloxy, aryloxy, O-alkyl, or O-aralkyl; (Y).sub.A is --CH.sub.2 NR.sub.2 R.sub.3 where R.sub.2 and R.sub.3 may be hydrogen, substituted alkyls, aryls, or together with N form a 5 to 7 membered heterocyclic group; and Ar is a substituted or unsubstituted aryl. These compounds are useful in the treatment of various cardiac arrhythmias.Type: GrantFiled: July 26, 1982Date of Patent: December 31, 1985Assignee: American Hospital Supply CorporationInventors: David M. Stout, William L. Matier
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Patent number: 4558150Abstract: Intermediates of the formula ##STR1## are disclosed. These compounds are useful in the preparation of amino thiol dipeptides possessing angiotensin converting enzyme inhibition activity and enkephalinase inhibition activity.Type: GrantFiled: December 10, 1984Date of Patent: December 10, 1985Assignee: E. R. Squibb & Sons, Inc.Inventors: Eric M. Gordon, Jollie D. Godfrey, Jr.
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Patent number: 4522824Abstract: The present invention relates to derivatives of tryptamine of formula: ##STR1## in which: R.sub.1 represents a CH.sub.2 OH group, a --C.tbd.N group, ##STR2## or a --COOR.sub.6 group in which R.sub.4, R.sub.5 and R.sub.6 denote a lower alkyl group or hydrogen;R.sub.2 represents hydrogen or a C.tbd.N group;R.sub.3 denotes hydrogen, a CH.sub.3 group or a CH.sub.2 OH group, and the addition salts of the products of formula I with the pharmaceutically acceptable, mineral or organic acids. It also relates to a process for preparing said compounds and to the drugs active on the cardiovascular system, containing said compounds.Type: GrantFiled: March 21, 1983Date of Patent: June 11, 1985Assignee: SanofiInventors: Jean Wagnon, Patrick Gautier, Jean-Pierre Gagnol
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Patent number: 4513142Abstract: A method of preparation of cationic dyestuffs having the formula ##STR1## wherein A, B, R, and R.sup.1 are defined in the specification carried out in the substantial absence of solvent and removing water formed in the reaction.Type: GrantFiled: August 30, 1982Date of Patent: April 23, 1985Assignee: Bayer AktiengesellschaftInventors: Roderich Raue, Volker Huhne, Hans-Peter Kuhlthau
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Patent number: 4506080Abstract: A process for the separation of serotonine from coffee wax wherein a solution of coffee wax is subjected to alkaline hydrolysis using a strong base in the presence of water in an inert atmosphere after which the reaction medium containing the serotonine is recovered characterized in that the solvent for the coffee wax is a compound having the general formula II:R--(OC.sub.2 H.sub.4).sub.x --OC.sub.n H.sub.2n OH IIwherein R is hydrogen or an alkyl group containing from 1 to 4 carbon atoms, x is 0 or 1 and n is an integer from 2 to 4 with the proviso that x cannot be 1 when n is 3 or 4. N-acetyl serotonine is prepared by acetylating serotonine to N, O-diacetyl serotonine and then selectively hydrolyzing the O-acetyl group. Melatonine is obtained by methylating N-acetyl serotonine in the 5-position. Mexamine is obtained by de-acetylating melatonine in a hot alkaline solution containing a water-insoluble alcohol and acidifying the alcohol phase with hydrochloric acid.Type: GrantFiled: July 1, 1983Date of Patent: March 19, 1985Assignee: Nestec S. A.Inventors: Raymond Bertholet, Pierre Hirsbrunner
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Patent number: 4495352Abstract: 1-Aryloxy-3-[(3-indolyl)-tert.-butyl]amino-2-propanols having a heterocyclic aryl-attached substituent or aryl-fused heterocyclic ring are antihypertensive agents having vasodilator and adrenergic .beta.-receptor blocking action.Type: GrantFiled: December 3, 1981Date of Patent: January 22, 1985Assignee: Mead Johnson & CompanyInventors: William E. Kreighbaum, William T. Comer
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Patent number: 4492694Abstract: 7-(3-Indolyl)glycylamido cephalosporins have good gram positive activity and favorable pharmacokinetics and are orally effective.Type: GrantFiled: April 12, 1983Date of Patent: January 8, 1985Assignee: Eli Lilly and CompanyInventors: Larry C. Blaszczak, Jan R. Turner
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Patent number: 4491664Abstract: A process for the production of an ergot alkaloid comprising intramolecularly cyclizing a 3-iminoethyl-4-trans-buta-1',3'-dienylindole to produce an 8-ergolene and as necessary converting the resultant ergolene into the desired ergot alkaloid.Type: GrantFiled: March 12, 1982Date of Patent: January 1, 1985Assignee: Sandoz Ltd.Inventor: Wolfgang Oppolzer
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Patent number: 4478750Abstract: A 1,2,3,4,5,6-hexahydro-6-phenyl-azepino[4,5-b]indole, or a pharmaceutically acceptable acid addition salt thereof is a useful neuroleptic, anti-depressant and anti-allergic agent.Type: GrantFiled: June 7, 1982Date of Patent: October 23, 1984Assignee: Sandoz Ltd.Inventor: Fulvio Gadient
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Patent number: 4452783Abstract: Aminoacid and peptide derivatives of the formula:A--NH--R.sub.1 --CO].sub.x [NH--R.sub.2 --CO].sub.y NH--R.sub.4 --COOHin which A, R.sub.1, R.sub.2, x and y have the meanings specified in claim 1 for formula I, and R4 is a residue of an .alpha.-aminoacid which, when A is 4-allyloxy-3-chloro-phenylacetyl and x and y are 0, contains at least 2 carbon atoms, and their physiologically acceptable salts and lower alkyl ester.These compounds and 4-allyloxy-3-chloro-phenylacetylglycine have anti-inflammatory activity and pharmaceutical compositions containing them are described.Type: GrantFiled: April 21, 1982Date of Patent: June 5, 1984Inventors: Robert E. Marks, James S. Burton, John A. Elvidge, Saresh Shah
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Patent number: 4404217Abstract: The present invention relates to the chemical products of general formula: ##STR1## in which R.sub.1 and R.sub.2 designate hydrogen; halogen, lower alkyl or lower alkoxy; R.sub.3 and R.sub.4 designate hydrogen, alkyl, alkoxy, halogen, nitro, acyl, alkylthio, alkylsulfinyl, alkylsulfonyl, a (CH.sub.2).sub.n COOR, (CH.sub.2).sub.2 CONHR, (CH.sub.2).sub.n NHCOOR or (CH.sub.2).sub.n NHCOR group; or R.sub.3 and R.sub.4 together form a heterocycle bonded to the benzene cycle; X.sub.1 is hydrogen, alkyl, hydroxymethyl or COOR and X.sub.2 is hydrogen or methyl; and to the pharmaceutically acceptable salts of said products. It also relates to a process for preparing said products and to the drugs active in particular on the cardiovascular system, containing at least one of said products.Type: GrantFiled: August 15, 1980Date of Patent: September 13, 1983Assignee: C. M. IndustriesInventors: Henri Demarne, Jean Wagnon
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Patent number: 4399289Abstract: Novel indole derivatives of the general formula I can be obtained by reacting, directly or indirectly, N,N-dimethyl-3-indolemethylamine with a Schiff base of the general formula II, ##STR1## in which R.sup.1 is cyano or methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl or butoxycarbonyl, and .phi. is phenyl. The successive hydrolysis of the indole derivatives of the general formula I in the presence of an acid and of a base gives tryptophane.Type: GrantFiled: March 26, 1981Date of Patent: August 16, 1983Assignee: Toray Industries, Inc.Inventors: Shinzo Imamura, Haruyo Sato, Hiroyoshi Kuramoto