Plural Hetero Rings Patents (Class 549/414)
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Patent number: 4665092Abstract: Alkenes of the formula (I) and epoxides (II) used to make them are useful as anti-inflammatory and antiallergic pharmaceuticals: ##STR1## wherein R.sup.1 =H or CH.sub.3 ; R.sup.2 =phenyl, substituted phenyl, benzyl or a cysteinyl moiety; R.sup.4 and R.sup.5 =alkyl; n=O or 1; and R.sup.3 is as described.Type: GrantFiled: October 3, 1985Date of Patent: May 12, 1987Assignee: Ortho Pharmaceutical CorporationInventors: Michael P. Ferro, Michael P. Wachter
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Patent number: 4659844Abstract: The invention relates to new cyclic ethers which are substituted in the .alpha.-position by an isocyanide-dichloride group, of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and n have the meaning indicated in the description, and to a process for their preparation.Type: GrantFiled: July 25, 1985Date of Patent: April 21, 1987Assignee: Bayer AktiengesellschaftInventors: Tillmann Hassel, Hanns P. Muller, Horst Boshagen
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Patent number: 4649156Abstract: The present invention provides a novel 6-nitroprostaglandin derivatives of the formula (I) ##STR1## wherein A, n, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are as defined in claim 1.The 6-nitroprostaglandin derivatives is useful as medicines because of its excellent pharmacological activities including platelet aggregation inhibiting activity, blood pressure lowering activity and anti-ulcerous activity, and useful as intermediate for other pharmaceutically active compounds such as 6-oxoprostaglandin derivatives, prostaglandin E.sub.1 derivatives, etc.Type: GrantFiled: July 19, 1985Date of Patent: March 10, 1987Assignee: Teijin LimitedInventors: Toshio Tanaka, Atsuo Hazato, Seizi Kurozumi
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Patent number: 4639534Abstract: Procedure for isolating lithium pseudomonate from a crude preparation containing pseudomonic acid by extracting the crude preparation into a suitable organic solvent in which pseudomonic acid is soluble, treating the extract with a lithium alkanoic acid and separating the resulting crystalline non-hygroscopic lithium pseudomonate, the crude preparation containing pseudomonic acid being a culture medium on or in which pseudomonic acid producing strains of bacteria have been grown, such as Pseudomonas fluorescens.Type: GrantFiled: December 21, 1984Date of Patent: January 27, 1987Assignee: Beecham Group p.l.c.Inventor: Alan D. Curzons
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Patent number: 4638060Abstract: Antibacterial activity is exhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof.Type: GrantFiled: April 29, 1985Date of Patent: January 20, 1987Assignee: E. R. Squibb & Sons, Inc.Inventors: Joseph E. Sundeen, William H. Koster, Robert Zahler
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Patent number: 4638002Abstract: The invention relates to new 2,3,4-trinor-1,5-inter-m-phenylene-PGI.sub.2 derivatives of the formula (I) ##STR1## wherein A stands for carboxy, cyano, tetrazolyl or --COOR.sup.3 or --CONR.sup.1 R.sup.2 ;R.sup.3 is C.sub.1-4 alkyl or an equivalent of a pharmacologically acceptable cation:R.sup.1 and R.sup.2 each stands for hydrogen, phenyl; C.sub.1-5 alkyl, optionally substituted by carboxy, hydroxy, phenyl or C.sub.2-5 alkoxycarbonyl; or C.sub.1-4 alkylsulfonyl; orR.sup.1 and R.sup.2 together form an .alpha.,.omega.-alkylene chain containing 3-6 carbon atoms;B stands for oxygen or methylene;Y is optionally bromo-substituted vinylene or a --C.tbd.C-- group:R.sup.4 stands for hydrogen or tetrahydro-pyran-2-yl;R.sup.5 represents an alkyl group containing 5-9 carbon atoms, which can be optionally interrupted by one or more oxygen atom(s) or --CH.dbd.CH-- or --C.tbd.Type: GrantFiled: December 30, 1983Date of Patent: January 20, 1987Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.Inventors: Istvan Szekely, Sandor Botar, Krisztina Dolgos nee Kekesi, Bela Bertok, Antal Gajary, Tamas Szabolcsi, Gabor Kovacs, Marianna Lovasz nee Gaspar
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Patent number: 4624696Abstract: Cyclohexenone derivatives of the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the meanings stated in the description, herbicides which contain these compounds and a method for controlling undesirable plant growth.Type: GrantFiled: October 9, 1985Date of Patent: November 25, 1986Assignee: BASF AktiengesellschaftInventors: Michael Keil, Rainer Becker, Dieter Jahn, Dieter Kolassa, Ulrich Schirmer, Wolfgang Will, Bruno Wuerzer, Norbert Meyer
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Patent number: 4608385Abstract: Use of an N-phenylcarbamate of the formula: ##STR1## as a fungicidal agent against phytopathogenic fungi, particularly their strains resistant to benzimidazole thiophanate fungicides and/or cyclic imide fungicides.Type: GrantFiled: October 22, 1982Date of Patent: August 26, 1986Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroshi Noguchi, Toshiro Kato, Junya Takahashi, Yukio Ishiguri, Shigeo Yamamoto, Katsuzo Kamoshita
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Patent number: 4608435Abstract: New benzo-1,4-quinones and salts thereof with organic or inorganic acid and bases have the formula I ##STR1## wherein p is 1 or 2 and q is 0 or 1, provided that p+q is 1 or 2, R is a residue of formula II ##STR2## wherein Q is selected from the residues --CO.sub.2 R.sub.4, --CON(R.sub.4)(R.sub.5), --OR.sub.5, --OCOR.sub.7, --N(R.sub.8)(R.sub.9), --PO(OR.sub.10)([O].sub.x R.sub.11), --SO.sub.2 R.sub.12, --CN, Halogen, --NO.sub.2 or --COR.sub.13, n is an integer from 1 to 20, k is 1 or 2 and x is 0 or 1, and R.sub.1 to R.sub.5 and R.sub.7 to R.sub.13 are as defined in the specification.The compounds of formula I are useful in photographic materials such as bleaching inhibitors in films of photographic silver dye bleach materials.Type: GrantFiled: April 28, 1983Date of Patent: August 26, 1986Assignee: Ciba-Geigy AGInventor: Frederick H. Howell
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Patent number: 4606753Abstract: Novel oxabicycloalkane ether of the formula ##STR1## wherein X is a single bond or --C(CH.sub.3).sub.2 -- and Y is a single bond or --CH.sub.2 -- with the proviso that both X and Y are not a single bond; R is H or --C(O)R.sup.3 in which R.sup.3 is H or certain hydrocarbyl groups; R.sup.1 is certain hydrocarbyl groups, or certain derivatives thereof, such as esters or carbamoyl compounds; and R.sup.2 is cyano or certain unsaturated, aromatic, heterocyclic, cycloalkyl, cycloalkenyl or secondary alkyl group, are useful as herbicides or plant growth regulators.Type: GrantFiled: June 15, 1984Date of Patent: August 19, 1986Assignee: Shell Oil CompanyInventor: James E. Powell
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Patent number: 4607026Abstract: This invention relates to stereoisomeric forms and mixtures thereof of compounds of the formula ##STR1## having insecticidal, nematocidal, and acaricidal properties.Type: GrantFiled: September 29, 1982Date of Patent: August 19, 1986Assignee: Roussel UclafInventors: Jean Tessier, Andre Teche
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Patent number: 4594094Abstract: Oxacycloalkane-alpha-(thio)carboxylic acid derivatives of the formula ##STR1## wherein R.sup.1 and R.sup.2 are H or optionally-substituted alkyl; n is 0 or 1; X is O or S and Y is NR.sup.4 R.sup.5 or when X is O then Y is also OH or OR.sup.3 in which R.sup.3, R.sup.4 and R.sup.5 is H or an optionally-substituted hydrocarbyl group; and W is an optionally-substituted unsaturated, cycloalkyl, secondary alkyl, aromatic or heterocyclic group, are useful as plant growth regulators, herbicides, intermediates and the like.Type: GrantFiled: April 4, 1983Date of Patent: June 10, 1986Assignee: Shell Oil CompanyInventor: Willy D. Kollmeyer
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Patent number: 4579958Abstract: The present invention describes 5-fluoro-3-oxa-prostacyclin (PGI.sub.2) derivatives of Formula I. These compounds are useful for the treatment of platelet dysfunction, atherosclerosis, hypertension and tumor cell metastasis. Also disclosed is the process for preparing them and the appropriate intermediates. ##STR1## wherein R.sup.1 is: (a) Na, K, or 1/2 Ca, or other pharmaceutically acceptable cation(b) NR.sup.3.sub.2, where R.sup.3 .dbd.H, methyl, ethyl, isopropyl or a combination of these groups;(c) Alkyl of 1 to 6 carbon atoms, either branched or straight chain(d) Hydrogenwherein OH on carbon 15 is optionally on carbon 16; wherein X.dbd.H, OCH.sub.3 or OC.sub.2 H.sub.5 when neither C.sub.5 -C.sub.6 or C.sub.6 -C.sub.7 is a double bond and nothing if C.sub.5 -C.sub.6 or C.sub.6 -C.sub.7 is a double bond;wherein R.sup.Type: GrantFiled: December 23, 1983Date of Patent: April 1, 1986Assignee: G. D. Searle & Co.Inventors: Stevan W. Djuric, Leland J. Chinn, Kurt J. Rorig
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Patent number: 4567052Abstract: The invention relates to novel N-alkylated 3-phenyl-4-cyanopyrrole derivatives of the formula I ##STR1## wherein R.sub.1 and R.sub.2, each independently of the other, are hydrogen, halogen, methoxy or methylthio,R.sub.3 is hydrogen or C.sub.1 -C.sub.8 haloalkyl,Y is hydroxy, halogen or the --O--C(O)--R.sub.4 group, andR.sub.4 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 haloalkyl, C.sub.2 -C.sub.6 alkenyl, 2-tetrahydrofuryl, 2-tetrahydropyranyl, C.sub.1 -C.sub.6 alkoxycarbonyl or the --CH(R.sub.5)--XR.sub.6 group, whereinX is oxygen or sulfur,R.sub.5 is hydrogen or C.sub.1 -C.sub.3 alkyl, andR.sub.6 is C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkoxy)-C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, phenyl or phenyl which is substituted by halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, or C.sub.1 -C.sub.6 alkoxycarbonyl.Type: GrantFiled: June 8, 1984Date of Patent: January 28, 1986Assignee: Ciba-Geigy CorporationInventor: Robert Nyfeler
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Patent number: 4564620Abstract: Pharmaceutically useful compounds are 5,6,7-trinor-4,8-inter-m-phenylene PGI.sub.2 derivatives such as 5,6,7-trinor-4,8-inter-m-phenylene-13,14-didehydro PGI.sub.2, 5,6,7-trinor-4,8-inter-m-phenylene-16,16-dimethyl PGI.sub.2, 5,6,7-trinor-4,8-inter-m-phenylene-17-.alpha.-methyl-20-homo PGI.sub.2, 5,6,7-trinor-4,8-inter-m-phenylene-17,18,19,20-tetranor-16-phenoxy PGI.sub.2, 5,6,7-trinor-4,8-inter-m-phenylene-20-isopropylidene PGI.sub.2, 5,6,7-trinor-4,8-inter-(5-methyl-1,3-phenylene) PGI.sub.2, and 5,6,7-trinor-4,8-inter-m-phenylene-2,3-didehydro-16,17,18,19,20-pentanor-1 5-phenyl PGI.sub.2. They are useful in treatment of ulcers, thrombii and hypertension for example.Type: GrantFiled: January 3, 1984Date of Patent: January 14, 1986Assignee: Toray Industries, Inc.Inventors: Kiyotaka Ohno, Hiroshi Nagase, Mamoru Ishikawa, Kazuhisa Matsumoto, Shintaro Nishio
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Patent number: 4559407Abstract: There is described a novel process for the manufacture of hydroquinone derivatives of the formula ##STR1## wherein R represents an ether protecting group, and their conversion into d-.alpha.-tocopherol starting from compounds of the formula ##STR2## wherein R has the above significance.Type: GrantFiled: October 11, 1983Date of Patent: December 17, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Richard Barner, Josef Hubscher
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Patent number: 4554363Abstract: Process for the preparation of bicyclic ketones containing blocked hydroxy groups, of general Formula I ##STR1## wherein R.sub.1 is the residues --CH.sub.2 OR.sub.2 wherein R.sub.2 means benzyl, dimethyl-tert-butylsilyl, diphenyl-tert-butylsilyl, dimethylphenylsilyl, tribenzylsilyl, or tetrahydropyranyl, ##STR2## with R.sub.2 having the meanings given above, R.sub.4 meaning hydrogen or methyl, and R.sub.5 meaning a straight-chain or branched-chain, saturated or unsaturated alkyl residue which can contain fluorine, chlorine, 1,2-methylene, 1,1-trimethylene, or methoxy substitutents, or a CH.sub.2 --X-Aryl residue with X meaning CH.sub.2 or O and Aryl meaning phenyl or a heterocyclic residue, which residues can be substituted by methyl, methoxy, fluorine, chlorine, bromine, or trifluoromethyl, or ##STR3## with the meanings for R.sub.2, R.sub.4, and R.sub.5 as indicated above, and R.sub.3 having the meanings set forth for R.sub.2, it being possible for R.sub.3 to be identical to R.sub.2 or different from R.sub.Type: GrantFiled: June 23, 1983Date of Patent: November 19, 1985Assignee: Schering AktiengesellschaftInventor: Helmut Vorbrueggen
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Patent number: 4551472Abstract: Unsymmetrical N-substituted bis-carbamoyl sulfide compounds exhibit exceptional broad spectrum pesticidal activity coupled with extremely low mammalian toxicity and phytotoxicity.Type: GrantFiled: January 9, 1984Date of Patent: November 5, 1985Assignee: Union Carbide CorporationInventor: Themistocles D. J. D'Silva
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Patent number: 4549015Abstract: New hydroquinone ether compounds of formula I are described: ##STR1## wherein p is 1 or 2 and q is 0 or 1, provided that p+q is 1 or 2, R is a residue of formula II ##STR2## and R.sub.o, R.sub.oo, R.sub.1, R.sub.2, R.sub.3, Q, n and k are as defined in the specification.The new compounds are useful e.g. as stabilizers in photographic material.Type: GrantFiled: June 14, 1983Date of Patent: October 22, 1985Assignee: Ciba-Geigy AGInventor: Frederick H. Howell
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Patent number: 4537623Abstract: Herbicidal 2-(oxaheterocycle or thiaheterocycle)-5-amino-3-oxo-4-(substituted-phenyl)-2,3-dihydrofurans and derivatives thereof. The compounds generally exhibit both pre-emergence and post-emergence phytotoxicity and are useful as herbicides and also plant growth regulating agents at low dosages.Type: GrantFiled: March 29, 1984Date of Patent: August 27, 1985Assignee: Chevron Research CompanyInventor: Carl E. Ward
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Patent number: 4537989Abstract: A compound of the formula ##STR1## wherein X.sup.1 is a free or an esterified carboxyl group, or a group of the formula: ##STR2## (R.sup.a and R.sup.b are each independently a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.7 cycloalkyl group, a benzyl group, a phenyl group, a phenyl group substituted with a halogen atom or a C.sub.1 -C.sub.4 alkyl group, or, when taken together with the adjacent nitrogen atom to which they are attached, they represent a 5 to 7 membered saturated heterocyclic group), Y is a group of the formula: ##STR3## (R.sup.6 is a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group) or ##STR4## (R.sup.6 is as defined above), R.sup.1 is a hydrogen atom, a hydroxyl group or a protected hydroxyl group, R.sup.2 is a hydrogen atom or R.sup.1 and R.sup.2, when taken together, mean a single linkage to form a double bond between the carbon atoms which they are linked, R.sup.3 is a hydroxyl group or a protected hydroxyl group, R.sup.4 is a hydrogen atom or a C.sub.1 -C.sub.Type: GrantFiled: April 15, 1983Date of Patent: August 27, 1985Assignee: Sumitomo Chemical Company, LimitedInventors: Keiichi Ono, Akihiko Sugie, Masami Muraoka, Michihiro Yamamoto
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Patent number: 4525203Abstract: Compounds of the formula ##STR1## wherein X is a single bond or --C(CH.sub.3).sub.2 ; Y is a single bond or --CH.sub.2 -with the proviso that both X and Y are not a single bond, and Z is H or alkyl; each R is H, hydroxy, oxo, methylene, alkyl or alkoxy, or one pair of adjacent R groups form a carbon-carbon bond; and R.sup.1 is H or alkyl, are useful as herbicides or plant growth regulators.Type: GrantFiled: June 15, 1984Date of Patent: June 25, 1985Assignee: Shell Oil CompanyInventors: George B. Payne, James E. Powell
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Patent number: 4514406Abstract: A compound of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are, same or different, each a hydrogen atom, a C.sub.1 -C.sub.3 alkyl group optionally substituted with halogen, an alkoxyalkyl or alkylthioalkyl group of the formula: R.sub.7 --Z--(CH.sub.2).sub.q --, a C.sub.2 -C.sub.3 alkenyl group, a C.sub.2 -C.sub.4 alkynyl group, a C.sub.1 -C.sub.2 alkoxy group, a C.sub.1 -C.sub.2 alkylthio group, a phenyl group, a pyridyl group, a furyl group or a thienyl group, or R.sub.1 and R.sub.2 may be combined together to form a saturated or unsaturated 5- or 6-membered ring having 0 to 2 oxygen or sulfur atom(s) within the ring, R.sub.3 and R.sub.4 are, same or different, each a hydrogen atom or a methyl group, R.sub.5 is a methyl group or a halogen atom, R.sub.6 is a C.sub.1 -C.sub.4 alkyl group, a methoxy group, a halogen atom, a trifluoromethyl group or a nitro group, R.sub.Type: GrantFiled: February 16, 1983Date of Patent: April 30, 1985Assignee: Sumitomo Chemical Company, LimitedInventors: Tadashi Ohsumi, Makoto Hatakoshi, Hirosi Kisida
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Patent number: 4496721Abstract: Symmetrical N-substituted bis-carbamoyl sulfide compounds exhibit exceptional broad spectrum pesticidal activity coupled with extremely low mammalian toxicity and phytotoxicity.Type: GrantFiled: February 7, 1983Date of Patent: January 29, 1985Assignee: Union Carbide CorporationInventor: Themistocles D. J. D'Silva
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Patent number: 4484000Abstract: New hydroquinones having the formula: ##STR1## wherein p is 1 or 2 and q is 0 or 1, provided that p+q is 1 or 2; R is a residue of formula: ##STR2## wherein Q is selected from the residues --COZR.sub.4 wherein Z is 0 or NR.sub.5, --OX wherein X is R.sub.5 or --COR.sub.7, --NR.sub.8 R.sub.9, --PO(OR.sub.10)[O].sub.x R.sub.11 wherein x is 0 or 1, --SO.sub.2 R.sub.12 or --CN, and salts thereof with organic or inorganic acid bases.The groups, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, k and n are defined hereafter.These compounds are used as stabilizers in photographic materials.Type: GrantFiled: June 18, 1982Date of Patent: November 20, 1984Assignee: Ciba-Geigy AGInventor: Frederick H. Howell
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Patent number: 4479945Abstract: New inter-m-phenylene-PGI.sub.2 derivatives are prepared of the general formula I ##STR1## wherein R.sup.1 stands for hydrogen, alkyl containing 1 to 4 carbon atoms or a pharmaceutically acceptable primary, secondary, tertiary or quaternary ammonium cation or a metal cation,R.sup.2 and R.sup.3 stand independently on each other for hydrogen, alkanoly, aroyl or an acetal type or alkyl silyl type protecting group,R.sup.4 represents hydrogen or an alkyl group containing 1 to 4 carbon atoms,X stands for oxygen, or a--CH.sub.2 --group,Y stands for--C.tbd.C-- or a trans--CH.dbd.CW group, wherein W stands for chlorine, bromine or fluorine,Z represents an alkyl group having 6 to 9 carbon atoms, optionally substituted by one or more alkyl groups containing 1 to 4 carbon atoms or fluorine or it stands for an optionally substituted arylmethyl or aryloxy methyl group.The new compounds are active ingredients of pharmaceutical compositions having antiaggregatory activity.Type: GrantFiled: November 29, 1982Date of Patent: October 30, 1984Assignee: Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T.Inventors: Istv/a/ n Sz/e/ kely, S/a ndor Bot/a r, Marianna G. Lov/a/ sz, Krisztina K. Dolgos, G/a/ bor Kov/a/ cs, S/a/ ndor Vir/a/ g, Tam/a/ s Sz/u/ ts, Istv/a n R/a/ k/o/ czi, K/a/ roly Tihanyi, P/e/ ter K/o/ rm/o/ czy, P/a/ l Hadh/a/ zy, Istv/a n Stadler, Gy/o/ rgy Blask/o/, B/e/ la K/o/ szegi
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Patent number: 4476139Abstract: The antibiotic, L-681,217, having antibacterial and growth-permittant activity, is produced by fermentation of Streptomyces cattleya in a suitable nutrient media.Type: GrantFiled: September 29, 1982Date of Patent: October 9, 1984Assignee: Merck & Co., Inc.Inventors: August J. Kempf, Kenneth E. Wilson, Otto D. Hensens, Richard L. Monaghan, Sheldon B. Zimmerman, Eugene L. Dulaney
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Patent number: 4472428Abstract: Novel 5- or 7-monohalogenated or 5,7-dihalogenated .sup.6 -PGI.sub.1 and 5- or 7-monohalogenated or dihalogenated PGI.sub.2 (except 5-monofluorinated PGI.sub.2). The novel halogenated prostacyclins are useful for controlling vascular actions and also in organ transplantation, extra-corporeal circulation and the like. The present invention also provides processes for preparing the novel halogenated prostacyclins.Type: GrantFiled: December 4, 1981Date of Patent: September 18, 1984Assignee: Teijin LimitedInventors: Takeshi Toru, Kiyoshi Bannai, Takeo Oba, Toshio Tanaka, Noriaki Okamura, Kenzo Wantanabe, Seizi Kurozumi, Akira Ohtsu, Tatsuyuki Naruchi
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Patent number: 4463177Abstract: m-Hydroxyphenyl substituted compounds of formula ##STR1## where R is an organic radical and R.sup.1 is hydroen or an organic radical are prepared by dehydrohalogenating a compound of formula ##STR2## (where X is chlorine or bromine, and R and R.sup.1 have the above meanings). Preferred novel starting materials of formula (II) are of the formula ##STR3## (where R.sup.1 and X are as above, n is 2,3 or 4, R.sup.2 is hydrogen or lower alkyl and R.sup.3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, cycloalkyl(lower)alkyl or aryl(lower)alkyl).Type: GrantFiled: November 26, 1982Date of Patent: July 31, 1984Assignee: John Wyeth & Brother LimitedInventor: Robin G. Shepherd
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Patent number: 4451483Abstract: 2,3,4-trinor-1,5-inter-m-phenylene-prostacycline derivatives of the formula (I), ##STR1## wherein R.sup.1 is hydrogen, a C.sub.1-4 alkyl group, an alkali metal cation or a primary, secondary, tertiary or quaternary ammonium cation,R.sup.2 and R.sup.3 each represent hydrogen or a C.sub.1-4 alkanoyl, benzoyl, substituted benzoyl, tetrahydropyranyl, ethoxyethyl or tri-(C.sub.1-4 alkyl)-silyl group,R.sup.4 is hydrogen or a C.sub.1-4 alkyl group, andR.sup.5 is a hexyl, heptyl, phenoxymethyl or m-trifluoromethylphenoxymethyl group, orR.sup.5 represents a group of the general formula ##STR2## and in this latter formula Z is an amino group or an optionally halo-substituted C.sub.1-4 alkanoylamino, benzoylamino or tosylamino group, andR.sup.6 is a C.sub.Type: GrantFiled: April 9, 1982Date of Patent: May 29, 1984Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.Inventors: Istvan Szekely, Krisztina Kekesi, Mariann Lovasz nee Gaspar, Sandor Botar, Pal Hadhazy, Istvan Rakoczi, Laszlo Muszbek, Judit Skopal, Istvan Stadler, Karoly Horvath, Gabor Kovacs, Peter Kormoczy
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Patent number: 4439225Abstract: Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are H or alkyl; n is 0 or 1 and R is an unsaturated moiety, are useful as herbicides and plant growth regulators.Type: GrantFiled: June 14, 1982Date of Patent: March 27, 1984Assignee: Shell Oil CompanyInventor: Willy D. Kollmeyer
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Patent number: 4435583Abstract: Compounds of formula (I): ##STR1## wherein Y is halogen,R.sup.1 is hydrogen, a salt forming radical, alkyl or aralkyl,have antibacterial and/or antimycoplasmal activity.Type: GrantFiled: December 7, 1982Date of Patent: March 6, 1984Assignee: Beecham Group p.l.c.Inventors: Norman H. Rogers, Michael J. Crimmin
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Patent number: 4411911Abstract: Novel sulfonate derivatives represented by the formulaR.sub.1 SO.sub.3 CH.sub.2 CO(CH.sub.2).sub.n R.sub.2act to inhibit esterases and chymotripsin and are useful as antilipemic agents, anti-inflammatory agents, immunity controlling agents, etc.Type: GrantFiled: January 19, 1981Date of Patent: October 25, 1983Assignee: Taiho Pharmaceutical Company, LimitedInventors: Setsuro Fujii, Toshihiro Hamakawa, Kazuo Ogawa, Yoshiyuki Muranaka, Sadao Hashimoto
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Patent number: 4410712Abstract: There are provided antibiotics X-14873 A, G and H of the formulas ##STR1## wherein for X-14873A, R.sub.1 is CO.sub.2 H and R.sub.2 is ##STR2## for X-14873G, R.sub.1 is hydrogen and R.sub.2 is ##STR3## and for X-14873H, R.sub.1 is hydrogen and R.sub.2 is ##STR4## The compounds exhibit antibiotic activity. Also disclosed is a process to produce the above compounds.Type: GrantFiled: March 10, 1982Date of Patent: October 18, 1983Assignee: Hoffmann-La Roche Inc.Inventors: Chao-min Liu, Homer D. Tresner, John Westley
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Patent number: 4408059Abstract: Milbemycin and avermectin macrolides are synthesized by the cyclized linking of separately synthesized northern and southern hemisphere intermediates. The northern hemisphere intermediate is a spiroketal alkenyl aldehyde, and the southern hemisphere intermediate is an aryl alkenyl phosphine oxide anion.Type: GrantFiled: December 4, 1981Date of Patent: October 4, 1983Assignee: University Patents, Inc.Inventors: Amos B. Smith, III, Steven R. Schow
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Patent number: 4399147Abstract: Prostaglandin I.sub.2 analogues of the formula: ##STR1## [wherein X represents trans-vinylene or an ethylene group unsubstituted or substituted by a bromine atom at the C-5 position, Y represents trans-vinylene or ethylene, R.sup.1 represents hydrogen or an alkyl group containing from 1 to 12 carbon atoms, R.sup.2 represents hydrogen or methyl or ethyl, R.sup.3 represents a single bond or an alkylene group containing from 1 to 4 carbon atoms, R.sup.4 represents hydrogen, an alkyl group containing from 1 to 8 carbon atoms, a cycloalkyl group containing from 4 to 7 carbon atoms unsubstituted or substituted by at least one alkyl group containing from 1 to 8 carbon atoms, or a phenyl or phenoxy group unsubstituted or carrying at least one substituent selected from halogen atoms, the trifluoromethyl group and alkyl groups containing from 1 to 3 carbon atoms, and the wavy line attached to the carbon atoms in positions 6, 11 and 15 depicted in the formula represents .alpha.- or .beta.Type: GrantFiled: January 26, 1978Date of Patent: August 16, 1983Assignee: Ono Pharmaceutical Co. Ltd.Inventors: Masaki Hayashi, Yoshinobu Arai, Yoshitaka Konishi, Katsuichi Shimoji, Shuichi Ohuchida, Hirohisa Wakatsuka, Hiroyuki Ito
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Patent number: 4390707Abstract: A method for the preparation of cyclopentenones of the general formula (VIII): ##STR1## wherein n is 5-7, has been developed which proceeds via the acid catalyzed deprotection and rearrangement of novel substituted-.alpha.-hydroxymethylfurans of general formula (VII): ##STR2## wherein R is a hydroxyl protecting group, R.sub.1 and R.sub.2 are methyl or ethyl or together form --(CH.sub.2).sub.3 -- and n is as above described. Cyclopentenones of formula VIII are useful intermediates in prostaglandin analog synthesis.Type: GrantFiled: February 2, 1982Date of Patent: June 28, 1983Assignee: American Cyanamid CompanyInventor: Steven L. Peake
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Patent number: 4389410Abstract: Compounds of formula (II): ##STR1## wherein R is C.sub.1-20 alkyl; C.sub.3-8 cycloalkyl; C.sub.3-20 alkenyl; aralkyl; cycloalkylalkyl; heterocyclyl or heterocyclylalkyl; each being substituted with formyl; ##STR2## have activity against human and veterinary bacteria and mycoplasma. They may be produced by conventional methods and are used in conventional formulations.Type: GrantFiled: July 21, 1981Date of Patent: June 21, 1983Assignee: Beecham Group LimitedInventors: Peter J. O'Hanlon, Norman H. Rogers
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Patent number: 4374147Abstract: Compounds of formula (II): ##STR1## in which R represents a pharmaceutically acceptable ester-forming radical have antibacterial and antimycoplasmal activity. These compounds are produced by photo-oxidation of the corresponding 13-hydroxy compounds, optionally after having protected the glycol moiety.Type: GrantFiled: June 5, 1981Date of Patent: February 15, 1983Assignee: Beecham Group LimitedInventors: Kong Luk, Norman H. Rogers
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Patent number: 4367340Abstract: Compounds of the general formula I are disclosed as useful intermediates in the preparation of prostanoids: ##STR1## wherein A represents O or H, OR.sub.z ;R.sup.z represents hydrogen or a protecting group;R.sup.x represents hydrogen or a protecting group; andR.sup.y represents halogen, a substituted thio group, di-substituted amino group, or a group of the formula R.sup.2, and R.sup.2 represents a straight-or branched-chain alkyl alkenyl or alkynyl group which may optionally be substituted by one or more carboxyl, carboxylic acid ester, or free or protected hydroxyl, thiol, aldehyde or keto groups;with the provisos that R.sup.x is not hydrogen when A is O and R.sup.y is R.sup.2 ; and that when A is H, OR.sup.z R.sup.y is R.sup.2 and R.sup.x and R.sup.z are not both hydrogen.Processes for the preparation of these compounds and of 2-substituted 4-hydroxy-cyclopent-2-en-1-one derivatives are also disclosed.Type: GrantFiled: March 4, 1981Date of Patent: January 4, 1983Assignee: The Australian National UniversityInventors: Rodney W. Rickards, Melvyn Gill, Robert M. Christie
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Patent number: 4364950Abstract: 5-cyano-prostacyclins of the formula ##STR1## wherein R.sub.1 is OR.sub.2 or NHR.sub.3 ; R.sub.2 and R.sub.3 each independently is (a) H, (b) C.sub.1-10 -alkyl, (c) C.sub.1-10 -alkyl substituted by halo, C.sub.1-4 -alkoxy or phenyl, 1-naphthyl or 2-naphthyl, each optionally substituted as defined below, (d) C.sub.4-10 -cycloalkyl, (e) C.sub.4-10 -cycloalkyl substituted by C.sub.1-4 -alkyl, (f) phenyl, 1-naphthyl or 2-naphthyl, (g) phenyl, 1-naphthyl or 2-naphthyl substituted by 1-3 halogen atoms, phenyl, 1-3 alkyl groups of 1-4 C atoms each, or a chloromethyl-, fluoromethyl-, trifluoromethyl-, carboxyl-, hydroxy- or alkoxy-group of 1-4 C atoms, or (h) an aromatic, 5- or 6-membered heterocyclic ring containing one hetero atom which is O, N or S, the remaining atoms being carbon; R.sub.3 also possibly being an acyl group of a C.sub.Type: GrantFiled: November 2, 1981Date of Patent: December 21, 1982Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Helmut Vorbruggen, Bernd Raduchel, Jorge Casals-Stenzel, Ekkehard Schillinger, Michael H. Town
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Patent number: 4364951Abstract: Prostane derivatives of the formula ##STR1## wherein B is straight-chain or branched alkylene of 1-10 carbon atoms,A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH--, or --C.tbd.C--;W is hydroxymethylene or a ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position, and is optionally modified by replacement of the H atom with an ether or acyl group which is conventional for such replacements in prostaglandins and which is readily cleavable at physiological pH's;D and E together are a direct bond orD is straight-chain or branched alkylene of 1-10 carbon atoms, or, such an alkylene of 4-10 carbon atoms containing a double bond in the 2- or 3- position, all of which can optionally be substituted by fluorine, 1,2-methylene, 1,1-trimethylene, or methoxy;E is oxygen, sulfur, --C.tbd.C-- or a direct bond;R.sub.2 is C.sub.1-10, C.sub.2-10 alkenyl,each of which optionally is substituted phenyl, 1-naphthyl or 2-naphthyl, each of which is substituted as defined below; C.sub.Type: GrantFiled: November 2, 1981Date of Patent: December 21, 1982Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Helmut Vorbrueggen, Olaf Loge, Peter Vischer, Bernd Raduchel
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Patent number: 4362743Abstract: Compounds of formula (II): ##STR1## in which Y represents ##STR2## and R.sub.0 represents a C.sub.2-20 alkyl, C.sub.3-8 cycloalkyl, C.sub.4-20 alkenyl, arakyl, cycloalkylalkyl, heterocyclyl or heterocyclylalkyl group, which is substituted by a hydroxyiminohydrazono- or semicarbazono group, have activity against human and veterinary bacteria and mycoplasma. They may be produced by conventional methods and are used in conventional formulations.Type: GrantFiled: July 31, 1981Date of Patent: December 7, 1982Assignee: Beecham Group LimitedInventors: Norman H. Rogers, Peter J. O'Hanlon, Graham Walker
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Patent number: 4346228Abstract: 11-Oxoprostaglandin derivatives of the formula ##STR1## wherein R.sub.2 is a hydrogen atom or alkyl of 1-5 carbon atoms,R.sub.3 is alkyl of 1-5 carbon atoms, alkylaryl, cycloalkyl of 5-6 ring carbon atoms and a total of 5-10 carbon atoms; benzodioxol-2-yl, phenyl, naphthyl or phenyl or naphthyl substituted by phenyl, halogen, alkyl of 1-4 carbon atoms, chloromethyl, fluoromethyl, carboxyl or hydroxy;A is --CH.sub.2 --CH.sub.2 --, cis--CH.dbd.CH--, or trans--CH.dbd.CH--;B is --CH.sub.2 --CH.sub.2 -- or trans--CH.dbd.CH--,D and E collectively are a direct bond or D is alkylene of 1-5 carbon atoms and E is an oxygen or sulfur atom; esters thereof; readily cleavable 9,15 and 9,15 ethers thereof; methanesulfonylamides thereof, and physiologically acceptable salts thereof with bases; possess the activity of the corresponding natural prostaglandins with a surprisingly longer duration of effectiveness, greater selectivity, and better effects, and can be produced, e.g.Type: GrantFiled: April 15, 1976Date of Patent: August 24, 1982Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Eckehard Schillinger
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Patent number: 4341894Abstract: Sensitizers for photoconductive compositions and elements are disclosed. The sensitizers are 2,4,6 tri substituted pyrylium dye salts wherein at least one of said substituents is a 5 or 6 membered heterocyclic ring having at least one atom selected from the group consisting of N, O and S.Type: GrantFiled: April 26, 1979Date of Patent: July 27, 1982Assignee: Eastman Kodak CompanyInventors: Michael T. Regan, George A. Reynolds, Donald P. Specht, James A. VanAllan
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Patent number: 4340543Abstract: Sulfonium compounds represented by the formula ##STR1## have anticancer activity, immunostimulant activity and the like, and useful as the active components of drugs and agricultural chemicals.Type: GrantFiled: February 3, 1981Date of Patent: July 20, 1982Assignee: Taiho Pharmaceutical Company LimitedInventors: Akihide Koda, Mikio Hori, Mitsugi Yasumoto, Ichiro Yamawaki, Yuji Yamada, Katsuo Takikawa
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Patent number: 4338249Abstract: 16-Fluoro-prostaglandins and pharmaceutical compositions containing the same are prepared. They are useful, for example, as anti-ulcer agents.Type: GrantFiled: April 7, 1980Date of Patent: July 6, 1982Assignee: Farmitalia Carlo ErbaInventors: Renato Pellegata, Carmelo Gandolfi
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Patent number: 4330553Abstract: New PGI.sub.2 derivatives and a process for their preparation are disclosed of the formula (I) ##STR1## wherein Q is hydrogen, a pharmacologically acceptable cation, or lower alkyl;A is cis or trans --CH.dbd.CH--, --C.tbd.C--, or --CH.sub.2 --CH.sub.2 --;R.sup.13 is hydrogen or a C.sub.1 to C.sub.4 alkanoyl or is a blockinggroup of the formula R.sup.7 R.sup.8 R.sup.9 Si or ##STR2## wherein R.sup.7, R.sup.8 and R.sup.9 are the same or different and can be straight or branched chain alkyl groups having 1 to 4 carbon atoms and R.sup.10 and R.sup.11 are the same or different and can be hydrogen or methyl, and R.sup.12 represents methyl or ethyl, or is tetrahydropyran-2-yl;R.sup.4 is hydrogen or lower alkyl inthe .alpha. or .beta. steric position;R.sup.1 and R.sup.2 are each hydrogen or lower alkyl;Y is methylene, oxygen or an --NH-- group; andR.sup.3 is lower alkyl or phenyl which can be monosubstituted phenyl.Type: GrantFiled: November 10, 1980Date of Patent: May 18, 1982Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara R.T.Inventors: Vilmos Simonidesz, Agnes Papp nee Behr, Gabor Kovacs, Jozsef Ivanics, Julia Der nee Foldvary, Istvan Stadler, Istvan Pallagi