Polycyclo Ring System Having The Hetero Ring As One Of The Cyclos Patents (Class 549/354)
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Patent number: 5231196Abstract: The present invention relates to an improvement in the process for preparing a calixarene derivative in which the rotation of its benzene units are hindered and which comprises replacing all or a part of the hydrogen atoms of the hydroxyl groups of a calixarene derivative represented by the general formula: ##STR1## and is characterized by conducting the reaction in the presence of an alkaline earth metal. According to the present invention, an asymmetric calixarene derivative having a "cone" conformation can be selectively prepared by virtue of the template effect of the metal.Type: GrantFiled: December 14, 1990Date of Patent: July 27, 1993Assignee: Daicel Chemical Industries, Ltd.Inventors: Seiji Shinkai, Tsutomu Matsuda, Takashi Arimura, Kirosuke Kawabata, Kozo Tachibana
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Patent number: 5225437Abstract: Novel 1,2,4-trioxanes which possess anti-malarial activity.Type: GrantFiled: January 23, 1992Date of Patent: July 6, 1993Assignee: The Johns Hopkins UniversityInventors: Gary Posner, Chang H. Oh
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Patent number: 5216178Abstract: Novel aminoalkylthiodibenzoxepins, physiologically tolerable acid addition salts thereof, a method of preparing same, pharmaceutical and veterinary preparations including same and methods of treating by administering same are disclosed. These compounds are useful as analgesic, antidepressant and anticonvulsant agents. A process for selectively reducing olefins by alkaline earth metals in loweralkanols is also disclosed.Type: GrantFiled: August 15, 1991Date of Patent: June 1, 1993Assignee: Hoechst-Roussel Pharmaceuticals IncorporatedInventors: Helen H. Ong, Vernon B. Anderson, James A. Profitt
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Patent number: 5192765Abstract: Amines of the following formula: ##STR1## where the variables are defined in the specification are useful in the treatment of diseases associated with altered motility and/or tone of smooth muscle.Type: GrantFiled: June 6, 1991Date of Patent: March 9, 1993Assignee: Pfizer Inc.Inventors: David Alker, Robert J. Bass, Peter E. Cross
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Patent number: 5175286Abstract: A dibenz[b,e]oxepin derivative represented by the formula (I) ##STR1## wherein R.sup.1 and R.sup.2 are each hydrogen, halogen, lower alkyl or alkoxy; one of R.sup.3 and R.sup.4 is lower alkoxy, and other is a group represented by the formula (II) ##STR2## wherein R.sup.5 is hydrogen or lower alkyl, A is hydroxyl, --O(CH.sub.2).sub.m --R.sup.6 (wherein m is an integer of 1-6, R.sup.6 is hydrogen, lower alkyl or alkoxy, cycloamino, or lower alkoxycarbonyl), cycloamino, di-lower alkylamino or --NH(CH.sub.2).sub.n --R.sup.7 (wherein n is an integer of 0-3, R.sup.7 is hydrogen, hydroxyl, phenyl, thiazole or cycloamino).Type: GrantFiled: March 8, 1991Date of Patent: December 29, 1992Assignee: Hisamitsu Pharmaceutical Co., Inc.Inventors: Masaru Saita, Hisataka Inoue, Terumi Hachiya, Mikio Nakashima, Shigenori Yahiro, Yasuaki Taniguchi, Yoshiki Deguchi, Shoji Hamanaka, Masayoshi Tsuji, Kanji Noda
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Patent number: 5151529Abstract: A series of new compounds, called "the phomactins" is provided and may be isolated from the culture broth of fungi of the genus Phoma, especially Phoma sp. SANK 11486 (No. FERM BP-2598). These compounds are platelet activating factor antagonists and may be used for the treatment of disorders for which known such agents may also be used.Type: GrantFiled: October 10, 1990Date of Patent: September 29, 1992Assignee: Sankyo Company, LimitedInventors: Aiya Sato, Michihiro Sugano, Kouhei Furuya, Takeshi Oshima, Harumitsu Kuwano, Tadashi Hata, Hideyuki Haruyama
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Patent number: 5140027Abstract: Novel aminoalkylthiodibenzoxepins, physiologically tolerable acid addition salts thereof, a method of preparing same, pharmaceutical and veterinary preparations including same and methods of treating by administering same are disclosed. These compounds are useful as analgesic, antidepressant and anticonvulsant agents. A process for selectively reducing olefins by alkaline earth metals in loweralkanols is also disclosed.Type: GrantFiled: May 14, 1990Date of Patent: August 18, 1992Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Helen H. Ong, Vernon B. Anderson, James A. Profitt
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Patent number: 5125954Abstract: The present invention relates to novel bicyclo ether derivatives, to compositions containing them, and to their method of use especially to control the growth of undesired vegetation in rice.Type: GrantFiled: November 2, 1990Date of Patent: June 30, 1992Assignee: E.I. Du Pont de Nemours and CompanyInventors: James E. Powell, Richard B. Phillips
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Patent number: 5122361Abstract: Novel CNS dopamine D-2 receptors, such as the compound 5-iodo-7-N-[(1-ethyl-2-pyrrolidinyl)methyl]carboxamide-2,3-dihydrobenzofur an, are disclosed. These compounds are useful as imaging agents for D-2 receptors in the human brain and exhibit good brain retention and in vivo stability.Type: GrantFiled: April 17, 1989Date of Patent: June 16, 1992Assignee: Trustees of the University of PennsylvaniaInventors: Hank F. Kung, Raymond Murphy
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Patent number: 5118701Abstract: Novel tricyclic compound represented by formula (I): ##STR1## possess a TXA.sub.2 biosynthesis inhibiting activity and/or a TXA.sub.2 receptor antagonizing activity, and are expected to have preventive and therapeutic effects on ischemic diseases, cerebro-vascular diseases, etc.Type: GrantFiled: November 14, 1990Date of Patent: June 2, 1992Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Etsuo Oshima, Hiroyuki Obase, Akira Karasawa, Kazuhiro Kubo, Ichiro Miki, Akio Ishii
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Patent number: 5116863Abstract: Novel dibenz[b,e]oxepin derivatives are employed in the treatment and control of allergic conditions such as allergic asthma and also employed in the treatment of inflammation.Type: GrantFiled: March 2, 1987Date of Patent: May 26, 1992Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Etsuo Oshima, Toshiaki Kumazawa, Shizuo Otaki, Hiroyuki Obase, Kenji Ohmori, Hidee Ishii, Haruhiko Manabe, Tadafumi Tamura, Katsuichi Shuto
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Patent number: 5075330Abstract: The present invention includes N-hydroxyamide, N-hydroxyurea, N-hydroxythioamide, and N-hydroxythiourea derivatives of fenamates, indomethacin, cicloprofen, oxepinac, and indoprofen as dual inhibitors or selective ihibitors of cyclooxygenase and 5-lipoxygenase.Type: GrantFiled: October 16, 1990Date of Patent: December 24, 1991Assignee: Warner-Lambert Co.Inventors: Thomas R. Belliotti, Wiaczeslaw A. Cetenko, David T. Connor, Daniel L. Flynn, Catherine R. Kostlan, James B. Kramer, Jagadish C. Sircar
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Patent number: 5043415Abstract: The application describes nitrogen-containing an oxacalixarene or calixarene derivative of formula I: ##STR1## wherein m'+m"=0-8n=0-8m'.gtoreq.1/2(m'+M")3.ltoreq.m'+m"+n.ltoreq.8if n=0, m'+m".gtoreq.4R.sup.3 is H, halogen, or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof and R.sup.3 may be the same or different on each aryl group;R.sup.1 and R.sup.15 which may be the same or different are H or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof;R.sup.2 is selected from:R.sup.4 which is H, or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof, ##STR2## wherein R.sup.5 and R.sup.6 which may be the same or different are H, or hydrocarbyl, aryl, hydrocarbylaryl, or a substituted derivative thereof,-OR.sup.1, wherein R.sup.1 is as defined aboveand R.sup.17 which is a residue of a hydrocarbyl, aryl, or hydrocarbylaryl group or of a substituted derivative thereof providing a bond to another oxacalixarene or calixarene derivative of formula I wherein R.Type: GrantFiled: September 23, 1988Date of Patent: August 27, 1991Assignee: Loctite (Ireland) Ltd.Inventors: Stephen J. Harris, Maureen G. MacManus, John Guthrie
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Patent number: 5008285Abstract: Novel (6,11-dihydro-11-oxodibenz[b,e]oxepinyl)pentanoic acids and derivatives thereof, intermediates and processes for the preparation thereof, and methods for suppressing arthritis-like inflammation utilizing compounds or compositions thereof are disclosed.Type: GrantFiled: November 1, 1989Date of Patent: April 16, 1991Assignee: Hoechst-Roussel Pharmaceuticals, Inc.Inventors: Lawrence L. Martin, Linda L. Setescak
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Patent number: 4999363Abstract: Novel tricyclic compound represented by formula ##STR1## possess a TXA.sub.2 biosynthesis inhibiting activity and/or a TXA.sub.2 receptor antagonizing activity, and are expected to have preventive and therapeutic effects on ischemic diseases, cerebro-vascular diseases, etc.Type: GrantFiled: June 6, 1989Date of Patent: March 12, 1991Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Etsuo Oshima, Hiroyuki Obase, Akira Karasawa, Kazuhiro Kubo, Ichiro Miki, Akio Ishii
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Patent number: 4943571Abstract: Novel aminoalkylthiodibenzoxepins, physiologically tolerable acid addition salts thereof, a method of preparing same, pharmaceutical and veterinary preparations including same and methods of treating by administering same are disclosed. These compounds are useful as analgesic, antidepressant and anticonvulsant agents. A process for selectively reducing olefins by alkaline earth metals in loweralkanols is also disclosed.Type: GrantFiled: April 10, 1989Date of Patent: July 24, 1990Assignee: Hoechst-Roussel Phamraceuticals Inc.Inventors: Helen H. Ong, Vernon B. Anderson, James A. Profitt
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Patent number: 4904688Abstract: The present invention deals with dibenzo-oxocin-, dibenzo-thiocin-, dibenzo-azocin- and dibenzocyclo-octenamine derivatives suitable for use as antipsychotic compounds without extra-pyrimidal side-effects.Type: GrantFiled: March 8, 1989Date of Patent: February 27, 1990Assignee: Akzo N.V.Inventors: Duncan R. Rae, James Cairns
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Patent number: 4889858Abstract: The present invention relates to compounds represented by the general formula (I): ##STR1## wherein R.sub.1 is H or methoxy, R.sub.2 is H, methoxy, OH or F, R.sub.3 is H or F, R.sub.4 is H or F at 7-, 8- or 9-position, and .circle.Ar is a benzene, thiophene or pyridine ring, provided that (i) at least two of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are H, (ii) R.sub.2 or R.sub.3 is F when R.sub.4 is F, (iii) R.sub.1, R.sub.3 and R.sub.4 are H when R.sub.2 is methoxy or OH, (iv) R.sub.2 and R.sub.3 are not simultaneously F, and (v) R.sub.2 and R.sub.3 are H or F, and both R.sub.1 and R.sub.4 are H when .circle.Ar is a thiophene or pyridine ring, or a physiologically acceptable acid addition salt thereof.Type: GrantFiled: February 17, 1988Date of Patent: December 26, 1989Assignee: Dainippon Pharmaceutical Co., Ltd.Inventors: Hitoshi Uno, Mikio Kurokawa, Fuminori Sato, Shunsuke Naruto, Yoshinobu Masuda
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Patent number: 4882351Abstract: Novel tricyclic compounds having a TXA.sub.2 -antagonizing activity represented by formula (I): ##STR1## which strongly antagonize an action of thromboxane A.sub.2 and are expected to have preventive and therapeutic effects on ischemica diseases, cerebro-vascular diseases, etc.Type: GrantFiled: October 11, 1988Date of Patent: November 21, 1989Assignee: Roussel UclafInventors: Etsuo Oshima, Hiroyuki Obase, Akira Karasawa, Kazuhiro Kubo, Ichiro Miki, Akio Ishii
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Patent number: 4871865Abstract: The present invention relates to compounds of formula I ##STR1## or a salt, ester or amide thereof; wherein R.sup.1 is --CH.sub.2 --CH.sub.2 --, CH.sub.2 --O-- or --O--CH.sub.2 --; R.sup.2 and R.sup.3 are the same or different and are each hydrogen, C.sub.1-4 alkyl or taken together with the nitrogen comprise a nitrogen-containing heterocyclic ring having four to six ring members; R.sup.4 is a single bond or a C.sub.1-7 bivalent aliphatic hydrocarbon group and may be joined to the aromatic ring system at the 2,3,8 or 9 positions; n is 0 to 3, and their use as anithistamine and antiasthma agents.Type: GrantFiled: August 7, 1986Date of Patent: October 3, 1989Assignee: Burroughs Wellcome Co.Inventors: O. William Lever, Jr., Harry J. Leighton
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Patent number: 4855461Abstract: Oxacalixarenes of general formula I: ##STR1## wherein m=0-7 and n=1-8 with the proviso that m+n.ltoreq.8;R is hydrogen, halogen, or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof, and R may be the same or different on each aryl group; andR' is hydrocarbyl, aryl, hydrocarbylaryl, hydrocarbyloxy, aryloxy or hydrocarbylaryloxy or a substituted derivative thereof.The invention also provides a method of preparing oxacalixarenes of formula I, and cyanoacrylate adhesive compositions including as accelerator an oxacalixarene of formula I.Type: GrantFiled: January 20, 1988Date of Patent: August 8, 1989Assignee: Loctite (Ireland) Ltd.Inventor: Stephen J. Harris
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Patent number: 4855462Abstract: N-(Arylalkyl) dibenzoxepin propanamines useful as antihistamines, such as 3-dibenz[b,e]oxepin-11(6H)-ylidene-N-methyl-N-[6-[4-(1,1-dimethylethyl)phe nyl]-6-oxohexyl]-1-propanamine hydrochloride.Type: GrantFiled: June 17, 1988Date of Patent: August 8, 1989Assignee: Pennwalt CorporationInventors: Ronald C. Griffith, James J. Napier
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Patent number: 4837227Abstract: Novel aminoalkylthiodibenzoxepins, physiologically tolerable acid addition salts thereof, a method of preparing same, pharmaceutical and veterinary preparations including same and methods of treating by administering same are disclosed. These compounds are useful as analgesic, antidepressant and anticonvulsant agents. A process for selectively reducing olefins by alkaline earth metals in loweralkanols is also disclosed.Type: GrantFiled: May 28, 1985Date of Patent: June 6, 1989Assignee: Hoechst-Roussel Pharmaceuticals, Inc.Inventors: Helen H. Ong, Vernon B. Anderson, James A. Profitt
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Patent number: 4816591Abstract: 6,11-Dihydrodibenz[b,e]oxepin-acetic acids and derivatives having the general formula ##STR1## are prepared by multi-steps sequences. X is C.dbd.O, CHCl, CHBr, CH.sub.2 or CHOR.sup.4 ; Y is alkyl or alkoxy of 1 to 4 carbon atoms, halogen or trifluoromethyl; n is 0, 1, 2 or 3; Z is COOR.sup.5, CH.sub.2 OR.sup.5, CONR.sub.2.sup.5 or CONHOR.sup.5 ; and R.sup.1 -R.sup.5 are hydrogen or alkyl of 1 to 4 carbon atoms.These compounds and the physiologically tolerable salts thereof are useful as antiinflammatory and analgesic agents.Type: GrantFiled: November 5, 1979Date of Patent: March 28, 1989Assignee: American Hoechst CorporationInventors: Grover C. Helsley, Arthur R. McFadden, David Hoffman
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Patent number: 4810723Abstract: A compound, in the form of a pure optical isomer or a racemate, which is a dibenzo[be]oxepinacetic acid of the general formula (I) ##STR1## in which R1, R2 and R3, which may be the same or different, each represent hydrogen or methyl, XX represents a carbon-carbon bond or two hydrogen atoms, and YY represents a carbon-carbon bond or two hydrogen atoms, or a pharmaceutically acceptable salt thereof has useful therapeutic properties, especially as an anti-inflammatory.Type: GrantFiled: December 21, 1987Date of Patent: March 7, 1989Assignee: SynthelaboInventors: Thomas Purcell, Luc Rivron, Lydia Zard
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Patent number: 4751238Abstract: This invention relates to substituted alkyl amine derivatives of 6,11-dihydro-11-oxodibenz[b,e]oxepins of the formula: ##STR1## where X is hydrogen, halogen, lower alkoxy, lower alkyl, nitro, hydroxyl and CF.sub.3 ; R is H, and lower alkyl, R.sub.1 is CH.sub.3 SO.sub.3 and ##STR2## where R.sub.2 and R.sub.3 are the same of different and are hydrogen, lower alkyl, mesyl (CH.sub.3 SO.sub.2 --), and cycloalkyl loweralkyl; ##STR3## and the pharmaceutically acceptable acid addition salts thereof.Type: GrantFiled: June 18, 1986Date of Patent: June 14, 1988Assignee: Hoechst-Roussel Pharmaceuticals, Inc.Inventors: Lawrence L. Martin, Linda L. Setescak
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Patent number: 4745198Abstract: The invention concerns novel 4-phenyl-1,3-dioxan-5-ylalkenoic acid derivatives of the formula I having cis relative stereochemistry at positions 4 and 5 of the dioxane ring and wherein Ra and Rb are variously hydrogen, alkyl, halogenoalkyl, alkenyl, and optionally substituted aryl or arylalkyl, Rc is hydroxy, alkoxy or alkanesulphonamido, n is 1 or 2, A is ethylene or vinylene, Y is (2-5C)polymethylene optionally substituted by alkyl, and benzene ring B is optionally substituted phenyl, or, when Rc is hydroxy, a salt thereof. The acid derivatives antagonize one or more of the actions of thromboxane A.sub.2 (TXA.sub.2) and are expected to be of value in those disease conditions in which TXA.sub.2 is involved. The invention also provides pharmaceutical compositions containing an acid derivative of formula I, and processes for their chemical production.Type: GrantFiled: November 12, 1985Date of Patent: May 17, 1988Assignee: Imperial Chemical Industries PLCInventors: Andrew G. Brewster, Peter W. R. Caulkett
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Patent number: 4701466Abstract: Compounds of general formula ##STR1## in which R.sub.1, taken separately, denotes a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group, andR.sub.2, taken separately, denotes a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group or a phenylthio or phenylsulphonyl group, or alternativelyR.sub.1 and R.sub.2 together form an ethano bridge or, together with the two carbon atoms 8 and 9, form a fused benzene ring,R.sub.3 denotes a hydrogen atom or a methyl group andR.sub.4 denotes a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group or a cation of a base which is acceptable in pharmacology, the group CH(R.sub.3)COOR.sub.4 being at position 2 or 3. have uses in treatment of inflammation, pain and undesirable platelet aggregation.Type: GrantFiled: April 10, 1986Date of Patent: October 20, 1987Assignee: SynthelaboInventors: Thomas Purcell, Lydia Zard
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Patent number: 4670041Abstract: Compounds of the formula ##STR1## wherein X is (--CR.sub.4 R.sub.4 --).sub.m in which m is 0 or 1;Y is (--CR.sub.5 R.sub.6 --).sub.n in which n is 0, 1 or 2;Z is (--CR.sub.7 R.sub.7 --).sub.p in which p is 1, 2, or 3; the sum of m+n+p is an integer of 2 to 5, inclusive;R.sub.2 and R.sub.3 each is H or alkyl, and the like;R.sub.1 is H or alkyl; andW is an unsaturated moiety, are useful as plant growth regulators and herbicides.Type: GrantFiled: September 13, 1982Date of Patent: June 2, 1987Assignee: E. I. du Pont de Nemours and CompanyInventors: George B. Payne, Samuel B. Soloway, James E. Powell, Steven A. Roman, Willy D. Kollmeyer
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Patent number: 4645758Abstract: The invention concerns:Novel dibenz/b,e/oxepin and dibenz/b,e/thiepin compounds having the general formula: ##STR1## wherein X is O or S,R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and are each selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower alkynyl, lower cycloalkyl, lower alkoxy, lower alkylthio, lower alkylsulphinyl, lower alkylsulponyl, halogen, trifluoromethyl, trifluoromethylthio, lower dialkylsulphonamido, nitro, hydroxy, cyano, carbamyl, carboxy, lower alkoxycarbonyl, amino, N-lower alkylamino, N,N-diloweralkylamino, lower acylamido, lower alkanesulfonamido and lower acyl and, when on adjacent carbon atoms at the positions 2 and 3 and/or 8 and 9, two of the substituents R.sup.1 and R.sup.2 or R.sup.3 and R.sup.4 taken together may form a methylenedioxy group;R.sup.5 and R.sup.Type: GrantFiled: January 17, 1986Date of Patent: February 24, 1987Inventors: Nils-Erik Willman, Bengt C. H. Sjogren, Lennart G. Nordh, Gustav L. Persson, Goran H. Sjoholm
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Patent number: 4604128Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: m is an integer selected from 1 to 4;n is zero or an integer selected from 1 to 4;X are selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, alkylthio, sulfamoyl, substituted sulfamoyl, amino, substituted amino, the group --(CH.sub.2).sub.p C(.dbd.A)Z in which p is zero or one A is oxygen or sulfur, and Z is hydrogen, hydroxy, alkoxy, alkylthio, alkyl, substituted alkyl, amino or substituted amino, the group --NHC(.dbd.B)NR.sup.7 R.sup.8 in which B is oxygen or sulfur and R.sup.7 and R.sup.8 are hydrogen or alkyl;R.sup.1 is selected from hydrogen, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl; andR.sup.4 is selected from hydrogen, halogen, alkyl, cyano and alkoxycarbonyl.Type: GrantFiled: September 10, 1985Date of Patent: August 5, 1986Assignee: ICI Australia LimitedInventors: Keith G. Watson, John D. Wishart, Graeme J. Farquharson, Graham J. Bird, Lindsay E. Cross
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Patent number: 4596804Abstract: A dibenz[b,e]oxepin compound having an antiallergic activity is represented by the following general formula: ##STR1## wherein R.sub.1 represents a cyano group, a 5-tetrazolyl group, a carbamoyl group or --CO.sub.2 R.sub.3 wherein R.sub.3 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a 1-(ethoxycarbonyloxy)ethyl group, and R.sub.2 represents a 4-alkylpiperazino group wherein the alkyl group has 1 to 5 carbon atoms, a 3-quinuclidinylamino group or --X--(CH.sub.2).sub.n --NR.sub.4 R.sub.5 wherein X represents --NH--, --S -- or --O--, R.sub.4 and R.sub.5 are same or different and each represents an alkyl group having 1 to 5 carbon atoms and n represents 2 or 3; and the pharmaceutically acceptable acid addition salts or metal salts thereof.Type: GrantFiled: June 26, 1984Date of Patent: June 24, 1986Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Hiroshi Takizawa, Yoshimasa Oiji, Kenji Ohmori, Katsuichi Shuto
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Patent number: 4585788Abstract: 6,11-Dihydrodibenz[b,e]oxepin-acetic acids and derivatives having the general formula ##STR1## are prepared by multi-step sequences. X is C.dbd.O, CHCl, CHBr, CH.sub.2 or CHOR.sup.4 ; Y is alkyl or alkoxy of 1 to 4 carbon atoms, halogen or trifluoromethyl; n is 0, 1, 2 or 3; Z is COOR.sup.5, CH.sub.2 OR.sup.5, CONR.sub.2.sup.5 or CONHOR.sup.5 ; and R.sup.1 -R.sup.5 are hydrogen or alkyl of 1 to 4 carbon atoms.These compounds and the physiologically tolerable salts thereof are useful as antiinflammatory and analgesic agents.Type: GrantFiled: April 10, 1974Date of Patent: April 29, 1986Assignee: American Hoechst CorporationInventors: Grover C. Helsley, Arthur R. McFadden, David Hoffman
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Patent number: 4576960Abstract: This invention relates to 6,11-dihydro-11-oxo-dibenz[b, e]oxepin derivatives of the formula ##STR1## where Y is hydrogen, alkyl, alkoxy, halogen and trifluoromethyl, n is 0, 1, 2 or 3; R.sub.9 is hydrogen and alkyl; R is ##STR2## where Hal is a halogen; ##STR3## where R.sub.10 is hydrogen, alkyl and benzyl of the formula ##STR4## where Z is hydrogen, alkyl, alkoxy, halogen, trifluoromethyl, nitro, and amino; where n is 0, 1, 2 or 3; p is 1 or 2; q is 0, 1 or 2; R.sub.1 to R.sub.7 are the same or different and are hydrogen and alkyl; and R.sub.8 is hydrogen, alkyl and phenyl; and R.sub.9 is hydrogen and alkyl, and where appropriate pharmaceutically acceptable acid or base addition salts thereof.Type: GrantFiled: April 4, 1983Date of Patent: March 18, 1986Assignee: Hoechst Roussel Pharmaceuticals IncorporatedInventors: Lawrence L. Martin, Linda L. Setescak
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Patent number: 4548929Abstract: Novel heterobicyclic compounds of Formula I, processes for preparing same and pesticidal compositions and methods are described.Type: GrantFiled: April 18, 1983Date of Patent: October 22, 1985Assignee: SDS Biotech CorporationInventors: Thomas A. Magee, Robert D. Battershell, Lawrence E. Limpel, Andrew W. Ho, Arthur W. Friedman, H. Glenn Corkins, William W. Brand, Russell Buchman, Louis Storace, Edmond R. Osgood
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Patent number: 4526891Abstract: This invention relates to compounds of the formula: ##STR1## where X is hydrogen, halogen, lower alkoxy, lower alkyl, nitro, hydroxyl and CF.sub.3 ; R is H, and lower alkyl, R.sub.1 is CH.sub.3 SO.sub.3 and ##STR2## where R.sub.2 and R.sub.3 are the same or different and are hydrogen, lower alkyl, mesyl (CH.sub.3 SO.sub.Type: GrantFiled: March 10, 1983Date of Patent: July 2, 1985Assignee: Hoechst Roussel Pharmaceuticals Inc.Inventors: Lawrence L. Martin, Linda L. Setescak
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Patent number: 4523022Abstract: The present invention concerns the novel, sugar-ring expansion for synthesis of novel analogs of spectinomycin or C-6' analogs of spectinomycin from known aminomethyldihydrospectinomycin and analogs thereof. Additionally, the invention concerns the novel synthesis of novel 7 membered sugar-ring analogs of dihydrospectinomycin and C-6' analogs thereof from novel 7 membered sugar-ring spectinomycin and C-6' analogs thereof by treatment with NaBH.sub.4.Type: GrantFiled: July 7, 1983Date of Patent: June 11, 1985Assignee: The Upjohn CompanyInventor: Richard C. Thomas
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Patent number: 4515946Abstract: This invention relates to 6,11-dihydro-11-oxo-dibenz[b,e]oxepin derivatives of the formula ##STR1## where Y is alkyl, alkoxy, halogen or trifluoromethyl, n is 0, 1, 2 or 3; R is ##STR2## where Hal is a halogen; ##STR3## where n is 0, 1, 2 or 3; p is 1 or 2; q is 0, 1, or 2; R.sup.1 to R.sup.7 are the same or different and are hydrogen and alkyl and R.sup.8 is hydrogen, alkyl and phenyl; and R.sup.9 is alkyl and the pharmaceutically acceptable acid addition salts thereof.Type: GrantFiled: December 23, 1981Date of Patent: May 7, 1985Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Lawrence L. Martin, Linda L. Setescak
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Patent number: 4499290Abstract: 10-oxytetracyclo[4.2.1.2.sup.3,8.0.sup.2,5 ]undecane and its lower alkyl-substituted congeners and their synthesis by contacting a tricyclo[4.2.1.0.sup.2,5.0]non-7-en-3-yl-methanol with a strong acid so that cyclization occurs. The compounds of this invention have desirable fragrance characteristics and their stability against oxidative deterioration during storage, transportation, and use enhances their usefulness as fragrance materials.Type: GrantFiled: October 24, 1983Date of Patent: February 12, 1985Assignee: Ethyl CorporationInventor: Lawrence H. Shepherd, Jr.
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Patent number: 4496557Abstract: Compounds corresponding to the general formula: ##STR1## in which X and Y identical or different, represent a hydrogen or a halogen atom, a lower alkyl, a lower alkoxy or a trifluormethyl group,A represents a methylene group, a direct bond or an imino--NR.sub.3 -- group in which R.sub.3 is a hydrogen atom or a lower alkyl or lower alkanoyl groupR.sub.1 and R.sub.2 identical or different, each represents a hydrogen atom or a lower alkyl group, or together with the nitrogen atom to which they are attached they form a pyrrolidino, piperidino or methyl-4 piperazine group, andn represents an integer from 1 to 3, in their racemic or optical isomeric forms, as well as their salts of addition with a therapeutically compatible mineral or organic acid.These compounds are useful as antidepressants.Type: GrantFiled: August 16, 1982Date of Patent: January 29, 1985Assignee: AdirInventors: Charles Malen, Jean-Claude Poignant
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Patent number: 4496582Abstract: There are described analgesic dibenz[b,f]oxepins having the general formula ##STR1## wherein n is an odd integer 1-7 inclusive; R is --CO.sub.2 R.sub.1 or --CH.sub.2 OR.sub.2 where R.sub.1 is H, C.sub.1-5 lower alkyl, aralkyl, ##STR2## R.sub.3 being C.sub.1-5 lower alkyl; X and Y are each independently hydrogen, halogen, trifluoromethyl, C.sub.1-5 lower alkoxy, C.sub.1-5 lower alkyl, C.sub.1-5 lower alkylthio, or hydroxy; and the dotted line may be a bond or nothing.Type: GrantFiled: December 12, 1983Date of Patent: January 29, 1985Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Helen H. Ong, Matthew J. Flynn
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Patent number: 4496447Abstract: Compounds of the formula ##STR1## wherein A, X, Z, R.sup.1, R.sup.2, R.sup.3, R.sup.4, n and m are defined hereinbelow are effective photoinitiators especially for the photopolymerization of ethylenically unsaturated compounds and for the curing of printing inks.Type: GrantFiled: December 21, 1982Date of Patent: January 29, 1985Assignee: Merck Patent Gesellschaft mit beschraenkter HaftungInventors: Jurgen Eichler, Claus Herz, Karl-Heinz Neisius, Gregor Wehner
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Patent number: 4417063Abstract: A method for the preparation of 6,11-dihydro-11-oxodibenz[b,e]oxepin-acetic acids having pharmaceutical activity is disclosed. Compounds represented by the formula: ##STR1## wherein R is OH or Cl are provided as intermediates. An aldehyde of the formula: ##STR2## wherein R.sub.1 is a lower alkyl, e.g., 1 to 4 carbon atoms, is reacted with chloroform and aqueous base to form an .alpha.-hydroxy dicarboxylic acid. Alternatively, the aldehyde can be converted to the corresponding cyanohydrin, which is then converted to the corresponding .alpha.-hydroxy dicarboxylic acid. The .alpha.-hydroxy dicarboxylic acid can also be prepared from reaction of a halogenated toluate of the formula: ##STR3## wherein X is Cl or Br with mandelic acid or a derivative thereof of the formula: ##STR4## wherein R.sub.3 and R.sub.4 are independently selected from hydrogen and alkyl of 1 to 4 carbon atoms. The .alpha.-hydroxy dicarboxylic acid is cyclized and then converted to the oxepin acetic acid by reduction. Alternatively, the .Type: GrantFiled: May 18, 1981Date of Patent: November 22, 1983Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Thomas B. K. Lee, George E. Lee, Gregory M. Jobin
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Patent number: 4396550Abstract: Novel dibenz [b,e] oxepin derivatives represented by the general formula: ##STR1## wherein R.sub.11 represents an alkyl group containing 1 to 5 carbon atoms, an alkoxy group containing 1 to 5 carbon atoms, a halogen atom, a cyclohexyl group or a phenyl group; and R.sub.21 represents ##STR2## wherein X represents a hydrogen atom, a hydroxy group, an amino group or a substituted aralkyl group containing 7 to 20 carbon atoms, and n represents 0 or an integer of 1 to 3 ##STR3## or (3) --NH--(CH.sub.2).sub.n --Y, wherein Y represents an alkylamino group containing 1 to 5 carbon atoms, an aralkyl group containing 7 to 20 carbon atoms, a substituted aralkyl group, an aralkyloxy group containing 7 to 20 carbon atoms, an aralkylamino group containing 7 to 20 carbon atoms, a heterocyclic ring or a substituted heterocyclic ring, and n has the same meaning as defined before; provided that when R.sub.Type: GrantFiled: April 21, 1981Date of Patent: August 2, 1983Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Hiroshi Takizawa, Osamu Morita, Yoshimasa Oiji, Tamotsu Hashimoto
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Patent number: 4356186Abstract: Novel acetic acid derivatives of the formula: ##STR1## wherein X is oxygen or sulfur; R.sub.1 is hydrogen or a lower alkyl; R.sub.2 is hydroxy, an alkoxy, an alkenyloxy, a cycloalkyloxy, an aryloxy, a substituted aryloxy, an aryl-lower alkoxy, a substituted aryl-lower alkoxy, an aryl-lower alkenyloxy, a substituted aryl-lower alkenyloxy, an .omega.-disubstituted amino-lower alkoxy, a lower alkoxycrbonyl-lower alkoxy, a lower alkoxy-lower alkoxy, a hydroxy-lower alkoxy-lower alkoxy, an acyl-lower alkoxy, or a group ##STR2## wherein R.sub.3 is hydrogen, hydroxy, a lower alkyl, an aryl-lower alkyl, a hydroxy-lower alkyl, or a carboxy-lower alkyl, R.sub.4 is hydrogen, a lower alkyl or a hydroxy-lower alkyl, or the R.sub.3 and R.sub.4 may combine together with the nitrogen atom to which they are joined to form a heterocyclic group; and the group --CH(R.sub.1)COR.sub.Type: GrantFiled: March 20, 1981Date of Patent: October 26, 1982Assignee: Dainippon Pharmaceutical Co., Ltd.Inventors: Hitoshi Uno, Mikio Kurokawa, Hideo Nakamura