Two Rings Only Patents (Class 562/500)
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Patent number: 4219562Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an optionally halo-substituted hydroxcarbyl group, and X is --C(O)Cl, --C(O)Br or C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.Type: GrantFiled: March 8, 1979Date of Patent: August 26, 1980Assignee: Shell Oil CompanyInventor: Steven A. Roman
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Patent number: 4219565Abstract: A cyclopropane compound having the formula ##STR1## wherein R is a residue of certain alcohols; andR.sup.1 is hydrogen, or certain optionally halogenated hydrocarbyl groups,are highly active pesticides.Type: GrantFiled: June 26, 1979Date of Patent: August 26, 1980Assignee: Shell Oil CompanyInventor: Steven A. Roman
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Patent number: 4219563Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is a hydrocarbyl group, W is a chlorine or bromine atom or --OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.Type: GrantFiled: June 21, 1979Date of Patent: August 26, 1980Assignee: Shell Oil CompanyInventor: James E. Powell
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Patent number: 4218402Abstract: 2,2-Dimethyl-3-((oxyimino)methyl)cyclopropanecarboxylic acids are prepared by treating the mixed anhydride of acetic and caronaldehydic acids with an acid addition salt of a hydroxylamine or of a hydrocarbyloxylamine followed by hydrolysis of the oxyimino-substituted product thereby obtained.Type: GrantFiled: July 16, 1979Date of Patent: August 19, 1980Assignee: Shell Oil CompanyInventor: Steven A. Roman
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Patent number: 4215142Abstract: Prostaglandin E.sub.1 analogues of the general formula: ##STR1## [wherein Y represents ethylene or trans-vinylene, Z represents ethylene or trans-vinylene, R.sup.1 represents a hydrogen atom, an alkyl group containing from 1 to 12 carbon atoms, an aralkyl group containing from 7 to 12 carbon atoms, a cycloalkyl group containing from 4 to 7 carbon atoms and unsubstituted or substituted by at least one alkyl group containing from 1 to 6 carbon atoms, a phenyl group unsubstituted or substituted by at least one chlorine atom, trifluoromethyl group, alkyl group containing from 1 to 4 carbon atoms or phenyl group, a --C.sub.m H.sub.2m COOR.sup.5 group (wherein m represents an integer of from 1 to 12 and R.sup.5 represents a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms), a --C.sub.n H.sub.2n OR.sup.6 group (wherein R.sup.6 represents a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms and n represents an integer of from 2 to 12), or a ##STR2## group (wherein R.sup.7 and R.Type: GrantFiled: September 8, 1978Date of Patent: July 29, 1980Assignee: Ono Pharmaceutical Co. Ltd.Inventors: Masaki Hayashi, Katsuichi Shimoji, Yoshinobu Arai
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Patent number: 4211792Abstract: (1R,trans)-cyclopropane compounds, substantially free of other stereoisomers, and having the formula ##STR1## wherein X is chlorine, bromine or OR in whichR is hydrogen, a salt-forming cation, an alkyl group or residues of certain other alcohols; andR.sup.1 is certain optionally halogenated hydrocarbyl groups, are highly active pesticides or intermediates therefore.Type: GrantFiled: February 21, 1979Date of Patent: July 8, 1980Assignee: Shell Oil CompanyInventors: Steven A. Roman, Samuel B. Soloway
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Patent number: 4211789Abstract: (1R,cis)-cyclopropane compounds, substantially free of other stereoisomers, and having the formula ##STR1## wherein R is the residue of certain alcohols; andR.sup.1 is hydrogen, or certain optionally halogenated hydrocarbyl groups, are highly active pesticides.Type: GrantFiled: February 21, 1979Date of Patent: July 8, 1980Assignee: Shell Oil CompanyInventors: Steven A. Roman, Samuel B. Soloway
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Patent number: 4208428Abstract: The invention relates to prostaglandin analogues of the general formula: ##STR1## (wherein A represents a grouping of the formula: ##STR2## B represents an alkylene group containing from 1 to 7 carbon atoms or a group ##STR3## (wherein the group --(CH.sub.2).sub.n --may be attached to the ortho, meta or para position of the phenyl ring and m and n, which may be the same or different, each represent an integer from 1 to 5 inclusive, the sum of the integers represented by m and n being from 2 to 6 inclusive), X represents ethylene or cis-vinylene, Y represents ethylene or trans-vinylene, W represents ethylene or trans-vinylene, Z represents a halogen atom, and R.sup.1 represents a hydrogen atom or an alkyl group containing from 1 to 12 carbon atoms) and cyclodextrin clathrates of such acids and esters and, when R.sup.1 represents a hydrogen atom, non-toxic salts thereof, which possess characteristic prostaglandin-like properties.Type: GrantFiled: July 13, 1978Date of Patent: June 17, 1980Assignee: Ono Pharmaceutical Co. Ltd.Inventors: Masayasu Kurono, Nobuyuki Hamanaka, Shigeru Sakuyama, Takeshi Chiba, Hisao Nakai
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Patent number: 4202989Abstract: This disclosure describes novel 15-deoxy-16-hydroxy-16-substituted prostanoic acids and congeners thereof having utility as bronchodilators as hypotensive agents, and as agents for the control of excessive gastric secretion.Type: GrantFiled: August 1, 1977Date of Patent: May 13, 1980Assignee: American Cyanamid CompanyInventors: Middleton B. Floyd, Jr., Martin J. Weiss, Charles V. Grudzinskas, Sow-Mei L. Chen
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Patent number: 4202988Abstract: This disclosure describes derivatives, analogs, and congeners of prostanoic acid having a terminal cyclic moiety in the .beta.-chain which possess the pharmacological activities associated with the prostaglandins.Type: GrantFiled: March 30, 1977Date of Patent: May 13, 1980Assignee: American Cyanamid CompanyInventors: Allan Wissner, Martin J. Weiss, Karel F. Bernady
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Patent number: 4198521Abstract: This disclosure describes novel 15-deoxy-16-hydroxy-16-substituted prostanoic acids and congeners thereof having utility as bronchodilators, as hypotensive agents and as agents for the control of excessive gastric secretion.Type: GrantFiled: December 5, 1977Date of Patent: April 15, 1980Assignee: American Cyanamid CompanyInventors: Middleton B. Floyd, Jr., Martin J. Weiss, Charles V. Grudzinskas, Sow-Mei L. Chen
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Patent number: 4198430Abstract: Optionally active 13,14-dehydro-11-deoxy prostaglandins useful in inhibiting gastric secretions and as anti-asmthmatic agents are disclosed.Type: GrantFiled: March 8, 1976Date of Patent: April 15, 1980Assignee: Farmitalia Carlo Erba S.p.A.Inventors: Carmelo Gandolfi, Renato Pellegate, Franco Faustini, Angelo Fumagalli
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Patent number: 4197407Abstract: This disclosure describes derivatives, analogs, and congeners of prostanoic acid having a terminal cyclic moiety in the .beta.-chain which possess the pharmacological activities associated with the prostaglandins.Type: GrantFiled: March 30, 1977Date of Patent: April 8, 1980Assignee: American Cyanamid CompanyInventors: Allan Wissner, Martin J. Weiss, Karel F. Bernady
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Patent number: 4192950Abstract: This disclosure describes novel 15-deoxy-16-hydroxy-16-substituted prostanoic acids and congeners thereof having utility as bronchodilators as hypotensive agents, and as agents for the control of excessive gastric secretion.Type: GrantFiled: September 22, 1977Date of Patent: March 11, 1980Assignee: American Cyanamid CompanyInventors: Middleton B. Floyd, Jr., Martin J. Weiss, Charles V. Grudzinskas, Sow-Mei L. Chen
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Patent number: 4189597Abstract: This disclosure describes certain 11-(2-hydroxyethylthio)-9-keto-prostenoic acid E series derivatives, and their intermediates, useful as bronchodilators and inflammatory medeator release inhibitors.Type: GrantFiled: October 17, 1977Date of Patent: February 19, 1980Assignee: American Cyanamid CompanyInventors: Martin J. Weiss, Gerald J. Siuta
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Patent number: 4181674Abstract: The stereospecific alkylation of a novel 3-endo-protected hydroxyl-tricyclo[3,2,0,0.sup.2,7 ]heptan-6-one is described using a range of lithium-, copper or magnesium-containing organometallic reagents. This reaction provides a 5-endo-protected hydroxyl-bicyclo[2,2,1]-heptan-2-one system from which prostaglandin compounds of the F series having a protecting group at the 9-position hydroxyl group may readily be obtained by a sequence of reactions.Type: GrantFiled: December 2, 1976Date of Patent: January 1, 1980Assignee: Allen & Hanburys LimitedInventors: Roger F. Newton, Stanley M. Roberts, David K. Rainey, Michael J. Dimsdale
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Patent number: 4180677Abstract: This disclosure describes novel 15-hydroxy prostanoic acid derivatives having anti-ulcer, bronchodilator, and hypotensive activity.Type: GrantFiled: October 28, 1977Date of Patent: December 25, 1979Assignee: American Cyanamid CompanyInventors: Robert E. Schaub, Martin J. Weiss
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Patent number: 4180675Abstract: The present invention relates to 15-cycloalkyl-prostaglandins of the formula: ##STR1## wherein A represents a grouping of the formula: ##STR2## W represents ethylene or trans-vinylene, X represents ethylene or cis-vinylene, Y represents ethylene or trans-vinylene, R represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 12 carbon atoms, R.sup.1 represents a hydrogen atom or a methyl or ethyl group, R.sup.2 represents a straight- or branched-chain alkyl group containing from 2 to 8 carbon atoms or a phenyl group unsubstituted or substituted by an alkyl group containing from 1 to 3 carbon atoms, R.sup.3 represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 3 carbon atoms, and n represents 4 or 5 and cyclodextrin clathrates of such acids and esters and, when R represents a hydrogen atom, non-toxic salts thereof.These new compounds exhibit characteristic prostaglandin-like activities.Type: GrantFiled: December 5, 1977Date of Patent: December 25, 1979Assignee: Warner-Lambert CompanyInventors: Masaki Hayashi, Seiji Kori, Isao Ohyama, Sadahiko Iguchi, Takanori Okada
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Patent number: 4152524Abstract: This disclosure describes novel 15-hydroxy prostanoic acids and derivatives thereof useful as bronchodilators and hypotensive agents.Type: GrantFiled: January 6, 1977Date of Patent: May 1, 1979Assignee: American Cyanamid CompanyInventors: Robert E. Schaub, Martin J. Weiss
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Patent number: 4152527Abstract: The 15-substituted-.omega.-pentanorprostaglandins and various intermediates employed in their preparation. The novel prostaglandins of this invention have been found to have activity profiles comparable to the parent prostaglandins, but exhibit a greater tissue specificity of action.Type: GrantFiled: December 27, 1973Date of Patent: May 1, 1979Assignee: Pfizer Inc.Inventors: Hans-Jurgen E. Hess, Thomas K. Schaaf
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Patent number: 4139717Abstract: 1,3-Dicarbonyl compounds useful as medicines, agricultural chemicals, perfumes, and their intermediates are prepared by reacting a specific .alpha.,.beta.-unsaturated carbonyl compound with a specific organic copper lithium compound in the presence of an aprotic inert organic solvent, and then reacting the reaction product with an organic carboxylic acid halide or anhydride. In particular, novel 2-acyl-3-substituted cyclopentan-1-ones and 2-acyl-3-substituted cyclohexan-1-ones having important physiological activities are provided.Type: GrantFiled: January 4, 1977Date of Patent: February 13, 1979Assignee: Teijin LimitedInventors: Seizi Kurozumi, Takeshi Toru, Toshio Tanaka, Shuzi Miura, Makiko Kobayashi, Sachio Ishimoto
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Patent number: 4138582Abstract: Analogues of prostaglandins A, E, and F in which the C.sub.13 -C.sub.20 chain of the natural prostaglandins is replaced by a cycloalkenyl or a hydroxycycloalkenyl moiety such that vinylene radical and the hydroxyl group of the ring respectively retain their natural sequential positions at C.sub.13 -C.sub.14 and C.sub.15, inhibit aggregation of platelets in vitro and exhibit useful cardiovascular activity in vivo.Type: GrantFiled: June 6, 1977Date of Patent: February 6, 1979Assignee: Miles Laboratories, Inc.Inventors: Warren D. Woessner, William G. Biddlecom, Henry C. Arndt, George P. Peruzzotti, Charles J. Sih
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Patent number: 4138583Abstract: Analogues of prostaglandins A, E, and F in which the C.sub.13 -C.sub.20 chain of the natural prostaglandins is replaced by a cycloalkenyl or a hydroxycycloalkenyl moiety such that vinylene radical and the hydroxyl group of the ring respectively retain their natural sequential positions at C.sub.13 -C.sub.14 and C.sub.15, inhibit aggregation of platelets in vitro and exhibit useful cardiovascular activity in vivo.Type: GrantFiled: June 6, 1977Date of Patent: February 6, 1979Assignee: Miles Laboratories, Inc.Inventors: Warren D. Woessner, William G. Biddlecom, Henry C. Arndt, George P. Peruzzotti, Charles J. Sih
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Patent number: 4134911Abstract: A novel 3-endo-protected hydroxyl-tricyclo[3,2,0,0.sup.2,7 ]-heptan-6-one is described which can be alkylated stereospecifically to give a 5-endo-protected hydroxyl-bicyclo [2,2,1]heptan-2-one which may then be converted via a sequence of reactions into prostaglandins of the F-series having a protecting group at the 9-position. The synthesis of the tricyclo[3,2,0,0.sup.2,7 ]heptan-6-one is also described.Type: GrantFiled: December 2, 1976Date of Patent: January 16, 1979Assignee: Allen & Hanburys LimitedInventor: Stanley M. Roberts
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Patent number: 4131737Abstract: This disclosure describes novel 15-deoxy-16-hydroxy-16-substituted prostanoic acids and conomers thereof having utility as bronchodilators as hypotensive agents, and as agents for the control of excessive gastric secretion.Type: GrantFiled: March 30, 1977Date of Patent: December 26, 1978Assignee: American Cyanamid CompanyInventors: Middleton B. Floyd, Jr., Martin J. Weiss, Charles V. Gredeinskas, Sow-mei C. Chen
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Patent number: 4128720Abstract: Prostaglandins of the formula: ##STR1## wherein A represents a grouping of the formula: ##STR2## X represents ethylene or cis-vinylene, Y represents ethylene or trans-vinylene, R represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 12 carbon atoms, R.sup.1 represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 10 carbon atoms, R.sup.2 represents a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms, R.sup.3 represents a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms, a cycloalkyl group containing from 4 to 7 carbon atoms, or a grouping of the formula: ##STR3## wherein R.sup.4 and R.sup.5 each represents a hydrogen or halogen atom, a trifluoromethyl group or an alkyl group containing from 1 to 3 carbon atoms, or R.sup.2 and R.sup.Type: GrantFiled: February 11, 1976Date of Patent: December 5, 1978Assignee: Ono Pharmaceutical CompanyInventors: Masaki Hayashi, Seiji Kori, Hajimu Miyake
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Patent number: 4126634Abstract: Aminosulfonylcarboxylic acids and their manufacture from diamines and chlorosulfonylcarboxylic acids.Type: GrantFiled: August 1, 1977Date of Patent: November 21, 1978Assignee: BASF AktiengesellschaftInventors: Lucien Thil, Martin Fischer, Wolfgang Kindscher
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Patent number: 4117119Abstract: Prostaglandin analogues of the formula: ##STR1## wherein A represents a grouping of the formula: ##STR2## X represents trans-vinylene or ethylene and Y represents cis-vinylene or ethylene, R represents hydrogen or alkyl of 1 through 12 carbon atoms, R.sup.1, R.sup.2 and R.sup.3 represent hydrogen, or alkyl of 1 through 12 carbon atoms or an aryl group, with the proviso that at least one of the symbols R.sup.1, R.sup.2 and R.sup.3 represents an alkyl or aryl group, are new compounds possessing useful pharmacological properties; they are especially useful for the treatment of gastric ulceration.Type: GrantFiled: May 6, 1977Date of Patent: September 26, 1978Assignee: Ono Pharmaceutical CompanyInventors: Masayasu Kurono, Hisao Nakai, Takashi Muryobayashi
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Patent number: 4117014Abstract: Prostaglandin type compounds of the formula ##STR1## wherein X is --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH-cis or--C.tbd.C--; Y is CH.sub.2 or O; Q is--CH.sub.2 --CH.sub.2 --or --CH.dbd.CH--; Z is H, OH, CH.sub.3 or CH.sub.2 OH, R is a linear, branched or cyclo alkyl chain of 3 to 7 carbon atoms or certain other moieties, and R" and R'''are H or CH.sub.3. These compounds are prepared by essentially a one-step reaction from a new intermediate of the formula ##STR2## wherein Z, R, R" and Q have the above meaning and P is a removable protective group by condensation with a reactive moiety introducing the entire .alpha.-chain (R'''=CH.sub.3). If desired, the carbonyl function is subsequently reduced to W= --CH(OH)--. The intermediate is useful in making known and new PGEs useful as antihypertensives, gastric acid secretion inhibitors and smooth muscle stimulants.Type: GrantFiled: December 23, 1976Date of Patent: September 26, 1978Assignee: Abbott LaboratoriesInventors: Andre G. Pernet, Hiromasa Nakamoto, Naoyasu Ishizuka
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Patent number: 4115438Abstract: Novel bicycloalkyl analogues or derivatives of prostaglandin A, E and F are useful modifiers of smooth muscle activity. The compounds have valuable pharmacological properties as platelet antiaggregating agents and gastric antisecretory agents. The compounds are also valuable pharmacological agents for increasing femoral blood flow and decreasing blood pressure and heart rate.Type: GrantFiled: July 21, 1977Date of Patent: September 19, 1978Assignee: Miles Laboratories, Inc.Inventors: Warren Dexter Woessner, Charles John Sih, Harold Clinton Kluender, Henry Clifford Arndt, William Gerard Biddlecom