Polycyclo Ring System Having The Hetero Ring As One Of The Cyclos Patents (Class 549/354)
  • Patent number: 5231196
    Abstract: 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: Grant
    Filed: December 14, 1990
    Date of Patent: July 27, 1993
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Seiji Shinkai, Tsutomu Matsuda, Takashi Arimura, Kirosuke Kawabata, Kozo Tachibana
  • Patent number: 5225437
    Abstract: Novel 1,2,4-trioxanes which possess anti-malarial activity.
    Type: Grant
    Filed: January 23, 1992
    Date of Patent: July 6, 1993
    Assignee: The Johns Hopkins University
    Inventors: Gary Posner, Chang H. Oh
  • Patent number: 5216178
    Abstract: 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: Grant
    Filed: August 15, 1991
    Date of Patent: June 1, 1993
    Assignee: Hoechst-Roussel Pharmaceuticals Incorporated
    Inventors: Helen H. Ong, Vernon B. Anderson, James A. Profitt
  • Patent number: 5192765
    Abstract: 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: Grant
    Filed: June 6, 1991
    Date of Patent: March 9, 1993
    Assignee: Pfizer Inc.
    Inventors: David Alker, Robert J. Bass, Peter E. Cross
  • Patent number: 5175286
    Abstract: 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: Grant
    Filed: March 8, 1991
    Date of Patent: December 29, 1992
    Assignee: 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
  • Patent number: 5151529
    Abstract: 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: Grant
    Filed: October 10, 1990
    Date of Patent: September 29, 1992
    Assignee: Sankyo Company, Limited
    Inventors: Aiya Sato, Michihiro Sugano, Kouhei Furuya, Takeshi Oshima, Harumitsu Kuwano, Tadashi Hata, Hideyuki Haruyama
  • Patent number: 5140027
    Abstract: 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: Grant
    Filed: May 14, 1990
    Date of Patent: August 18, 1992
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: Helen H. Ong, Vernon B. Anderson, James A. Profitt
  • Patent number: 5125954
    Abstract: 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: Grant
    Filed: November 2, 1990
    Date of Patent: June 30, 1992
    Assignee: E.I. Du Pont de Nemours and Company
    Inventors: James E. Powell, Richard B. Phillips
  • Patent number: 5122361
    Abstract: 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: Grant
    Filed: April 17, 1989
    Date of Patent: June 16, 1992
    Assignee: Trustees of the University of Pennsylvania
    Inventors: Hank F. Kung, Raymond Murphy
  • Patent number: 5118701
    Abstract: 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: Grant
    Filed: November 14, 1990
    Date of Patent: June 2, 1992
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Etsuo Oshima, Hiroyuki Obase, Akira Karasawa, Kazuhiro Kubo, Ichiro Miki, Akio Ishii
  • Patent number: 5116863
    Abstract: 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: Grant
    Filed: March 2, 1987
    Date of Patent: May 26, 1992
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Etsuo Oshima, Toshiaki Kumazawa, Shizuo Otaki, Hiroyuki Obase, Kenji Ohmori, Hidee Ishii, Haruhiko Manabe, Tadafumi Tamura, Katsuichi Shuto
  • Patent number: 5075330
    Abstract: 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: Grant
    Filed: October 16, 1990
    Date of Patent: December 24, 1991
    Assignee: 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
  • Patent number: 5043415
    Abstract: 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: Grant
    Filed: September 23, 1988
    Date of Patent: August 27, 1991
    Assignee: Loctite (Ireland) Ltd.
    Inventors: Stephen J. Harris, Maureen G. MacManus, John Guthrie
  • Patent number: 5008285
    Abstract: 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: Grant
    Filed: November 1, 1989
    Date of Patent: April 16, 1991
    Assignee: Hoechst-Roussel Pharmaceuticals, Inc.
    Inventors: Lawrence L. Martin, Linda L. Setescak
  • Patent number: 4999363
    Abstract: 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: Grant
    Filed: June 6, 1989
    Date of Patent: March 12, 1991
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Etsuo Oshima, Hiroyuki Obase, Akira Karasawa, Kazuhiro Kubo, Ichiro Miki, Akio Ishii
  • Patent number: 4943571
    Abstract: 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: Grant
    Filed: April 10, 1989
    Date of Patent: July 24, 1990
    Assignee: Hoechst-Roussel Phamraceuticals Inc.
    Inventors: Helen H. Ong, Vernon B. Anderson, James A. Profitt
  • Patent number: 4904688
    Abstract: 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: Grant
    Filed: March 8, 1989
    Date of Patent: February 27, 1990
    Assignee: Akzo N.V.
    Inventors: Duncan R. Rae, James Cairns
  • Patent number: 4889858
    Abstract: 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: Grant
    Filed: February 17, 1988
    Date of Patent: December 26, 1989
    Assignee: Dainippon Pharmaceutical Co., Ltd.
    Inventors: Hitoshi Uno, Mikio Kurokawa, Fuminori Sato, Shunsuke Naruto, Yoshinobu Masuda
  • Patent number: 4882351
    Abstract: 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: Grant
    Filed: October 11, 1988
    Date of Patent: November 21, 1989
    Assignee: Roussel Uclaf
    Inventors: Etsuo Oshima, Hiroyuki Obase, Akira Karasawa, Kazuhiro Kubo, Ichiro Miki, Akio Ishii
  • Patent number: 4871865
    Abstract: 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: Grant
    Filed: August 7, 1986
    Date of Patent: October 3, 1989
    Assignee: Burroughs Wellcome Co.
    Inventors: O. William Lever, Jr., Harry J. Leighton
  • Patent number: 4855461
    Abstract: 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: Grant
    Filed: January 20, 1988
    Date of Patent: August 8, 1989
    Assignee: Loctite (Ireland) Ltd.
    Inventor: Stephen J. Harris
  • Patent number: 4855462
    Abstract: 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: Grant
    Filed: June 17, 1988
    Date of Patent: August 8, 1989
    Assignee: Pennwalt Corporation
    Inventors: Ronald C. Griffith, James J. Napier
  • Patent number: 4837227
    Abstract: 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: Grant
    Filed: May 28, 1985
    Date of Patent: June 6, 1989
    Assignee: Hoechst-Roussel Pharmaceuticals, Inc.
    Inventors: Helen H. Ong, Vernon B. Anderson, James A. Profitt
  • Patent number: 4816591
    Abstract: 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: Grant
    Filed: November 5, 1979
    Date of Patent: March 28, 1989
    Assignee: American Hoechst Corporation
    Inventors: Grover C. Helsley, Arthur R. McFadden, David Hoffman
  • Patent number: 4810723
    Abstract: 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: Grant
    Filed: December 21, 1987
    Date of Patent: March 7, 1989
    Assignee: Synthelabo
    Inventors: Thomas Purcell, Luc Rivron, Lydia Zard
  • Patent number: 4751238
    Abstract: 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: Grant
    Filed: June 18, 1986
    Date of Patent: June 14, 1988
    Assignee: Hoechst-Roussel Pharmaceuticals, Inc.
    Inventors: Lawrence L. Martin, Linda L. Setescak
  • Patent number: 4745198
    Abstract: 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: Grant
    Filed: November 12, 1985
    Date of Patent: May 17, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Andrew G. Brewster, Peter W. R. Caulkett
  • Patent number: 4701466
    Abstract: 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: Grant
    Filed: April 10, 1986
    Date of Patent: October 20, 1987
    Assignee: Synthelabo
    Inventors: Thomas Purcell, Lydia Zard
  • Patent number: 4670041
    Abstract: 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: Grant
    Filed: September 13, 1982
    Date of Patent: June 2, 1987
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: George B. Payne, Samuel B. Soloway, James E. Powell, Steven A. Roman, Willy D. Kollmeyer
  • Patent number: 4645758
    Abstract: 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: Grant
    Filed: January 17, 1986
    Date of Patent: February 24, 1987
    Inventors: Nils-Erik Willman, Bengt C. H. Sjogren, Lennart G. Nordh, Gustav L. Persson, Goran H. Sjoholm
  • Patent number: 4604128
    Abstract: 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: Grant
    Filed: September 10, 1985
    Date of Patent: August 5, 1986
    Assignee: ICI Australia Limited
    Inventors: Keith G. Watson, John D. Wishart, Graeme J. Farquharson, Graham J. Bird, Lindsay E. Cross
  • Patent number: 4596804
    Abstract: 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: Grant
    Filed: June 26, 1984
    Date of Patent: June 24, 1986
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Hiroshi Takizawa, Yoshimasa Oiji, Kenji Ohmori, Katsuichi Shuto
  • Patent number: 4585788
    Abstract: 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: Grant
    Filed: April 10, 1974
    Date of Patent: April 29, 1986
    Assignee: American Hoechst Corporation
    Inventors: Grover C. Helsley, Arthur R. McFadden, David Hoffman
  • Patent number: 4576960
    Abstract: 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: Grant
    Filed: April 4, 1983
    Date of Patent: March 18, 1986
    Assignee: Hoechst Roussel Pharmaceuticals Incorporated
    Inventors: Lawrence L. Martin, Linda L. Setescak
  • Patent number: 4548929
    Abstract: Novel heterobicyclic compounds of Formula I, processes for preparing same and pesticidal compositions and methods are described.
    Type: Grant
    Filed: April 18, 1983
    Date of Patent: October 22, 1985
    Assignee: SDS Biotech Corporation
    Inventors: 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
  • Patent number: 4526891
    Abstract: 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: Grant
    Filed: March 10, 1983
    Date of Patent: July 2, 1985
    Assignee: Hoechst Roussel Pharmaceuticals Inc.
    Inventors: Lawrence L. Martin, Linda L. Setescak
  • Patent number: 4523022
    Abstract: 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: Grant
    Filed: July 7, 1983
    Date of Patent: June 11, 1985
    Assignee: The Upjohn Company
    Inventor: Richard C. Thomas
  • Patent number: 4515946
    Abstract: 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: Grant
    Filed: December 23, 1981
    Date of Patent: May 7, 1985
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: Lawrence L. Martin, Linda L. Setescak
  • Patent number: 4499290
    Abstract: 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: Grant
    Filed: October 24, 1983
    Date of Patent: February 12, 1985
    Assignee: Ethyl Corporation
    Inventor: Lawrence H. Shepherd, Jr.
  • Patent number: 4496557
    Abstract: 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: Grant
    Filed: August 16, 1982
    Date of Patent: January 29, 1985
    Assignee: Adir
    Inventors: Charles Malen, Jean-Claude Poignant
  • Patent number: 4496582
    Abstract: 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: Grant
    Filed: December 12, 1983
    Date of Patent: January 29, 1985
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: Helen H. Ong, Matthew J. Flynn
  • Patent number: 4496447
    Abstract: 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: Grant
    Filed: December 21, 1982
    Date of Patent: January 29, 1985
    Assignee: Merck Patent Gesellschaft mit beschraenkter Haftung
    Inventors: Jurgen Eichler, Claus Herz, Karl-Heinz Neisius, Gregor Wehner
  • Patent number: 4417063
    Abstract: 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: Grant
    Filed: May 18, 1981
    Date of Patent: November 22, 1983
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: Thomas B. K. Lee, George E. Lee, Gregory M. Jobin
  • Patent number: 4396550
    Abstract: 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: Grant
    Filed: April 21, 1981
    Date of Patent: August 2, 1983
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Hiroshi Takizawa, Osamu Morita, Yoshimasa Oiji, Tamotsu Hashimoto
  • Patent number: 4356186
    Abstract: 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: Grant
    Filed: March 20, 1981
    Date of Patent: October 26, 1982
    Assignee: Dainippon Pharmaceutical Co., Ltd.
    Inventors: Hitoshi Uno, Mikio Kurokawa, Hideo Nakamura