Plural Rings In Alcohol Moiety Patents (Class 560/255)
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Patent number: 4285867Abstract: Compounds having the formula ##STR1## wherein ##STR2## R.sub.1 is hydrogen, benzyl or alkanoyl, X is C.sub.2-4 alkylene; andZ-W is alkyl, phenylalkyl or pyridylalkyl which can have an oxygen atom as part of the alkyl chain and their use as CNS agents, antidiarrheals and antiemetics. Processes for their preparation and intermediates therefor are described.Type: GrantFiled: September 19, 1980Date of Patent: August 25, 1981Assignee: Pfizer Inc.Inventors: Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4283569Abstract: Compounds useful for pharmacological and medicinal purposes having the formulae ##STR1## wherein R is H, C.sub.1 -C.sub.5 alkanoyl; R.sub.1 is H, benzyl, C.sub.1 -C.sub.5 alkanoyl, P(O)(OH).sub.2, --CO(CH.sub.2).sub.2 COOH or a basic acyl group; each of R.sub.2 and R.sub.4 is H, C.sub.1 -C.sub.6 alkyl, phenyl, pyridyl or (CH.sub.2).sub.y C.sub.6 H.sub.5 ; y is 1-4; R.sub.3 is H or CH.sub.3 ; Z is C.sub.1 -C.sub.13 alkylene or --(alk.sub.1).sub.m --O--(alk.sub.2).sub.n --; each of (alk.sub.1) and (alk.sub.2) is C.sub.1 -C.sub.13 alkylene with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.2) is not greater than 13; each of m and n is 0 or 1; and W is H, pyridyl, phenyl, fluorophenyl or chlorophenyl; intermediates therefor and methods for their preparation and use.Type: GrantFiled: September 13, 1977Date of Patent: August 11, 1981Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4282250Abstract: The present invention provides a composition suitable for external application against skin injuries and diseases, such as ulcera, [e.g., Ulcus Cruris (indolent leg ulcer)], burns, scalds, open skin wounds, and the like, and having as its active ingredient a compound of the general formula ##STR1## wherein Y is hydrogen or --OX in which X represents hydrogen, a carboxylic acid residue, or a derivative of a carboxylic acid residue, and R.sub.1 and R.sub.2 are alkyl groups, e.g., lower alkyl groups such as methyl, and mixtures of these compounds. The most active of these ingredients is the compound of the above formula wherein X is the acetyl ester of the 3-methyl-3-hydroxy-butanecarboxylic acid residue. When mixtures of compounds including said most active compound of said general formula are employed against the aforesaid skin injuries and diseases, a synergistic effect is obtained.Type: GrantFiled: January 6, 1978Date of Patent: August 4, 1981Inventor: Vassilios P. Papageorgiou
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Patent number: 4282248Abstract: The present invention relates to novel compounds of the general formula ##STR1## wherein R.sup.1 is --H or --CO--alk, wherein alk is lower alkyl of 1 to 5 carbon atoms; R.sup.2 is 1,1-dimethylheptyl or 1,2-dimethylheptyl, Q is --CH.sub.3 when A------B is a single bond, and Q is --CH.sub.2 OR.sup.4 when A------B is a double bond, and R.sup.4 is --H or --CO--alk where alk is lower alkyl of 1 to inclusive 5 carbon atoms.The invention relates both to the isomeric mixtures and to the individual isomers of the above compounds. Furthermore the invention relates to pharmaceutical compositions containing a compound defined above as active ingredient. The pharmaceutical compositions are of value as central nervous system depressants, as sedatives, as tranquilizers, as anticonvulsant agents, as effective agents against migraine, for the treatment of glaucoma, as antidiarrheal agents and as antiinflammatory agents.Type: GrantFiled: July 23, 1979Date of Patent: August 4, 1981Inventors: Raphael Mechoulam, Naphtali Lander, Shabtay Dikstein
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Patent number: 4279930Abstract: A process for treating inflammation locally or topically by administering a compound of the formula: ##STR1## wherein M and M' are hydrogen, hydroxy, halogen, lower alkyl of from 1 to 3 carbon atoms, lower alkoxy of from 1 to 3 carbon atoms; NH.sub.2, RNH, R'.sub.2 N where R is lower alkyl of from 1 to 3 carbon atoms or lower acyl of from 1 to 3 carbon atoms and R' is lower alkyl of from 1 to 3 carbon atoms; X, Y and Z are hydrogen, hydroxy, halogen, lower alkoxy of from 1 to 3 carbon atoms or lower acyloxy of from 1 to 6 carbon atoms, in association with appropriate pharmaceutical carriers.Type: GrantFiled: September 14, 1979Date of Patent: July 21, 1981Assignee: The Upjohn CompanyInventors: Charles M. Hall, Eldridge M. Glenn
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Patent number: 4276430Abstract: Dihydroxybenzoic acid derivatives and compositions containing same are useful for topical application to the skin as well as for systemic administration. The compounds are especially effective for providing an analgesic, anti-pyretic, and anti-inflammatory effect.Type: GrantFiled: July 26, 1979Date of Patent: June 30, 1981Assignee: The Procter & Gamble CompanyInventors: Herbert H. Reller, Herbert C. Kretschmar
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Patent number: 4275068Abstract: Novel alkylene glycol derivatives of the formula (1) ##STR1## in which R.sup.1 is the hydrogen atom, an alkyl group having 1-4 C-atoms or an aryl group, R.sup.2 is the hydrogen atom or an alkyl group having 1-4 C-atoms, R.sup.3 is the hydrogen atom or a group of the formula ##STR2## in which Z is an alkyl residue, an optionally substituted aryl residue or a heterocyclic residue and R.sup.4 is a residue of the formula ##STR3## in which R.sup.5 is the hydrogen atom or chlorine atom, or the methyl group, exhibit an advantageous activity in regard of lowering the cholesterol and triglyceride level in the blood. Production of the novel derivatives by reduction of the corresponding acids, or by reacting a phenol of the formula ##STR4## and an alcohol of the formula ##STR5## optionally with subsequent esterification, is described.Type: GrantFiled: April 23, 1979Date of Patent: June 23, 1981Assignee: Siegfried AGInventors: Kurt Thiele, Quazi Ahmed, Ulrich Jahn, Rudolf Adrian
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Patent number: 4270005Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl of 1 to 5 carbon atoms or --CO--(CH.sub.2).sub.p --NR'R" wherein p is 0 or an integer from 1 to 4; each of R' and R" when taken individually is hydrogen or alkyl of 1 to 4 carbon atoms; R' and R" when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrollo, pyrrolidino, morpholino and N-alkylpiperazino having from 1 to 4 carbon atoms in the alkyl group;R.sub.2 is selected from hydrogen, alkanoyl of 1 to 6 carbon atoms and benzoyl;R.sub.3 is selected from hydrogen, methyl and ethyl;R.sub.4 is selected from hydrogen, alkyl of 1 to 6 carbon atoms and benzyl;Z is selected from:(a) alkylene having from one to nine carbon atoms;(b) --(alk.sub.1).sub.m --X--(alk.sub.2).sub.n -- wherein each of (alk.sub.1) and (alk.sub.2) is alkylene having from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.Type: GrantFiled: September 24, 1979Date of Patent: May 26, 1981Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4268523Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl of 1 to 5 carbon atoms or --CO--(CH.sub.2).sub.p --NR'R" wherein p is 0 or an integer from 1 to 4; each of R' and R" when taken individually is hydrogen or alkyl of 1 to 4 carbon atoms; R' and R" when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrollo, pyrrolidino, morpholino and N-alkylpiperazino having from 1 to 4 carbon atoms in the alkyl group;R.sub.2 is selected from hydrogen, alkanoyl of 1 to 6 carbon atoms and benzoyl;R.sub.3 is selected from hydrogen, methyl and ethyl;R.sub.4 is selected from hydrogen, alkyl of 1 to 6 carbon atoms and benzyl;Z is selected from:(a) alkylene having from one to nine carbon atoms;(b) -(alk.sub.1).sub.m -X-(alk.sub.2).sub.n - wherein each of (alk.sub.1) and (alk.sub.2) is alkylene having from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.Type: GrantFiled: September 24, 1979Date of Patent: May 19, 1981Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4268692Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl of 1 to 5 carbon atoms or --CO--(CH.sub.2).sub.p --NR'R" wherein p is 0 or an integer from 1 to 4; each of R' and R" when taken individually is hydrogen or alkyl of 1 to 4 carbon atoms; R' and R" when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrollo, pyrrolidino, morpholino and N-alkylpiperazino having from 1 to 4 carbon atoms in the alkyl group;R.sub.2 is selected from hydrogen, alkanoyl of 1 to 6 carbon atoms and benzoyl;R.sub.3 is selected from hydrogen, methyl and ethyl;R.sub.4 is selected from hydrogen, alkyl of 1 to 6 carbon atoms and benzyl;Z is selected from:(a) alkylene having from one to nine carbon atoms;(b) -(alk.sub.1).sub.m -X-(alk.sub.2).sub.n -wherein each of (alk.sub.1) and (alk.sub.2) is alkylene having from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.Type: GrantFiled: September 24, 1979Date of Patent: May 19, 1981Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4268688Abstract: This invention relates to a process for the preparation of optically active aldehydes by the asymmetric catalytic hydroformylation of olefins. The process comprises the hydroformylation of olefinically unsaturated prochiral compounds in the presence of an optically active coordination compound containing a metal which is selected from the group consisting of rhodium, iridium, and cobalt.This invention describes a generalized process for the asymmetric hydroformylation of a wide variety of olefins in which a preponderance of one optical isomer is produced. It is especially useful for the preparation of natural products which may require the presence of only one optical isomer for their utilization, for example, as flavors, fragrances, and medications.The catalyst systems for the process of this invention are formed in the presence of carbon monoxide and hydrogen, from coordination compounds consisting of a central metal atom, rhodium, iridium, or cobalt, and at least one optically active ligand, e.g.Type: GrantFiled: February 16, 1973Date of Patent: May 19, 1981Assignee: Monsanto CompanyInventors: Harold B. Tinker, Arthur J. Solodar
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Patent number: 4258207Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO, --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 15, 1979Date of Patent: March 24, 1981Assignee: Shell Oil CompanyInventor: Steven A. Roman
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Patent number: 4254285Abstract: The invention disclosed herein relates to pharmacologically active prostaglandin derivatives of the E, F, or A series having on the terminal methylene carbon of the alpha chain a substituent selected from the group consisting of: ##STR1## wherein R is an alkyl group and R.sub.15 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, di-C.sub.1 -C.sub.4 -alkylamino, and phenyl orphenyl substituted with one or more substituents selected from the group consisting of C.sub.1 -C.sub.4 alkyl, OR, SR, F, or Cl wherein R is as previously defined.Type: GrantFiled: January 16, 1979Date of Patent: March 3, 1981Assignee: American Cyanamid CompanyInventor: Allan Wissner
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Patent number: 4243660Abstract: The invention relates to a composite insect attractant for male cabbage moths (Mamestra brassicae) containing (Z)-11-hexadecenyl acetate and (Z)-11-heptadecenyl acetate as active agents in a weight ratio of 70 to 90:80 to 1, optionally along with a liquid or solid adjuvant. An insect trap can contain the composition which is used for attracting and trapping cabbage moth. Their mating is disrupted by air permeation techniques. (Z)-11-heptadecenyl acetate is a synergistically active new compound. The composition according to the invention produces a significantly stronger stimulating reaction on male cabbage moths than the known sex lure compositions.Type: GrantFiled: April 19, 1979Date of Patent: January 6, 1981Assignee: Egyt Gyogyszervegyeszeti GyarInventors: Csaba Szantay, Lajos Novak, Miklos Toth, Jozsef Balla, Bela Stefko, Attila Kis-Tamas
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Patent number: 4243682Abstract: 4-(6-Substituted naphthyl)butan-2-ols,-butan-2-ones,-pentan-2-ols and -pentan-2-ones bearing a fluoro group in the naphthyl ring, and pro-drugs thereof, are anti-inflammatory agents. A typical embodiment is 4-(4-fluoro-6-methoxy-2-naphthyl)-butan-2-one.Type: GrantFiled: October 23, 1978Date of Patent: January 6, 1981Assignee: Beecham Group LimitedInventors: Alexander C. Goudie, Laramie M. Gaster
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Patent number: 4238397Abstract: Hydroxyl-terminated liquid polymers having an aliphatic polymeric backbone and sulfide linkages near the terminal portions of the polymer molecule are prepared by polymerizing (1) at least one vinylidene monomer having at least one terminal CH.sub.2 .dbd.C< group per monomer molecule, together with (2) a mixture of at least one hydroxyl-containing disulfide and at least one hydroxyl-containing trisulfide. Use of the above disulfide-trisulfide mixture permits viscosity control during polymerization with substantially less disulfide required than if the disulfide alone were used, and the resulting polymers have less odor and discolor less upon heating than if the disulfide alone were used.Type: GrantFiled: May 18, 1979Date of Patent: December 9, 1980Assignee: The B. F. Goodrich CompanyInventor: Jack C. Gilles
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Patent number: 4236025Abstract: The present invention relates to novel 2-decarboxy-2-aminomethyl-6-keto-PG compounds, which are useful for inducing a variety of prostacyclin-like pharmacological effects. Accordingly, these compounds are useful pharmacological agents for the same purposes for which prostacyclin is employed.Type: GrantFiled: October 17, 1979Date of Patent: November 25, 1980Assignee: The Upjohn CompanyInventor: Udo F. Axen
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Patent number: 4235822Abstract: The present invention relates to novel 2-decarboxy-2-hydroxymethyl-6-keto-PG compounds, which are useful for inducing a variety of prostacyclin-like pharmacological effects. Accordingly, these compounds are useful pharmacological agents for the same purposes for which prostacyclin is employed.Type: GrantFiled: October 17, 1979Date of Patent: November 25, 1980Assignee: The Upjohn CompanyInventor: Udo F. Axen
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Patent number: 4233206Abstract: A process for the production of a colored polyolefin molded articles comprising adding to a polyolefin either a compound of the formula D--CH.sub.2 O.OC--R]).sub.n as a colorant wherein D is the residue of a common organic pigment, R is an alkyl, alkenyl or aryl group having up to 20 carbon atoms and n is an integer of 1-4, or a mixture of the compound of the above formula with at least one usual pigment, to form a mixture, and then molding the mixture thereby producing the desired colored articles. This invention also relates to the compound of said formula and to a mixture thereof with at least one common pigment.Type: GrantFiled: November 6, 1975Date of Patent: November 11, 1980Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Hiromitsu Katsura, Morihiko Endo, Takashi Kanno
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Patent number: 4225619Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is perfluoroalkyl of 1 to 8 carbon atoms or 2,2,3,3-tetrafluoro-cyclobutyl,R.sub.2 and R.sub.4, which may be identical to or different from each other, are each hydrogen, alkyl of 1 to 10 carbon atoms, aliphatic acyl of 2 to 18 carbon atoms, benzoyl, salicyloyl or phenylacetyl, andR.sub.3 and R.sub.5, which may be identical to or different from each other, are each alkyl of 3 to 18 carbon atoms, halogen, nitro, p-toluenesulfonyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclododecyl, methylcyclohexyl, dimethylcyclohexyl, benzyl, methylthio or ##STR2## where R.sub.1, R.sub.2 and R.sub.4 have the meanings previously defined,Q is --CH.sub.2 -- or --S--, andG is R.sub.5, as above defined, orQ is R.sub.3, as above defined, andG is --CH.sub.2 -- or --S--,R.sub.3 may, in addition, also be hydroxyl, methoxy, methyl or cyano, andR.sub.5 may also be methyl, orone of substituents R.sub.3 and R.sub.Type: GrantFiled: March 19, 1979Date of Patent: September 30, 1980Assignee: Boehringer Ingelheim GmBHInventors: Rolf Brickl, Hans Eberhardt, Karl-Richard Appel, Uwe Lechner, Walter Merk
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Patent number: 4207238Abstract: Hydroxyl-terminated liquid polymers having an aliphatic polymeric backbone and sulfide linkages near the terminal portions of the polymer molecule are prepared by polymerizing (1) at least one vinylidene monomer having at least one terminal CH.sub.2 .dbd.C< group per monomer molecule, together with (2) a mixture of at least one hydroxyl-containing disulfide and at least one hydroxyl-containing trisulfide. Use of the above disulfide-trisulfide mixture permits viscosity control during polymerization with substantially less disulfide required than if the disulfide alone were used, and the resulting polymers have less odor and discolor less upon heating than if the disulfide alone were used.Type: GrantFiled: September 1, 1977Date of Patent: June 10, 1980Assignee: The B. F. Goodrich CompanyInventor: Jack C. Gilles
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Patent number: 4202822Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.1 series.Type: GrantFiled: December 8, 1977Date of Patent: May 13, 1980Assignee: American Cyanamid CompanyInventor: Allan Wissner
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Patent number: 4202991Abstract: Bicycloalkane derivatives of the formula ##STR1## wherein n is 1 or 2, R.sub.1 is lower alkyl, Acyl is alkanoyl, and Y is --S--R.sub.2, --SO.sub.m --R.sub.2, or ##STR2## wherein m is 1 or 2, R.sub.2 is alkyl, R.sub.3 is hydrogen or lower alkyl, R.sub.4 is acyl or phenyl optionally substituted with lower alkoxy, benzyloxy or alkanoyloxy; and Z is nitro, lower alkoxycarbonyl, lower alkanoyl, lower alkylsulfinyl, or lower alkylsulfonyl are useful intermediates in the total synthesis of steroids. The compounds are prepared by reacting a corresponding compound lacking the CH.sub.2 Y substituent with formaldehyde and a mercaptan or sulfinic acid, followed if desired by oxidation and optional salt condensation.Type: GrantFiled: December 27, 1976Date of Patent: May 13, 1980Assignee: Schering AktiengesellschaftInventors: Gerhard Sauer, Helmut Hauser, Gregor Haffer, Juergen Ruppert, Ulrich Eder, Rudolf Wiechert
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Patent number: 4201869Abstract: A multi-step, stereospecific total synthesis of steroids is disclosed. The starting materials for this process are the relatively inexpensive and readily available m-alkoxy acetophenones. The process is suitable for the preparation of racemic or optically active, medicinally valuable steroids, particularly A-ring aromatic steroids. This process features an early optical resolution and a unique asymmetric induction which insures the correct stereochemistry of the final steroidal product.Type: GrantFiled: February 21, 1978Date of Patent: May 6, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Noal Cohen, Gabriel Saucy
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Patent number: 4201864Abstract: Compounds of formula (I): ##STR1## wherein: m is 1 or 2; n is 4 to 8; X is CO, protected CO, or CROH wherein R is hydrogen or C.sub.1-4 alkyl and wherein the OH moiety may be protected; R.sub.1 is hydrogen or CO.sub.2 R.sub.1 represents an ester group in which the R.sub.1 moiety contains from 1 to 12 carbon atoms; R.sub.3 is hydroxy, or protected hydroxy; R.sub.2 and R.sub.4 are separately hydrogen, C.sub.1-9 alkyl, C.sub.5-8 cycloalkyl, C.sub.5-8 cycloalkyl-C.sub.1-6 alkyl, phenyl, phenyl C.sub.1-6 alkyl, naphthyl, naphthyl C.sub.1-6 alkyl, any of which phenyl or naphthyl moieties may be substituted by one or more halogen, trifluoromethyl, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or nitro groups; or R.sub.2 and R.sub.4 taken with the carbon atom to which they are joined represent a C.sub.5-8 cycloalkyl group; and salts thereof; except that when one of R.sub.2 and R.sub.4 is hydrogen or C.sub.1-4 alkyl then the other of R.sub.2 and R.sub.4 cannot be hydrogen or C.sub.Type: GrantFiled: November 22, 1978Date of Patent: May 6, 1980Assignee: Beecham Group LimitedInventors: Frederick Cassidy, Gordon Wootton
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Patent number: 4197245Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the A.sub.1 series.Type: GrantFiled: December 8, 1977Date of Patent: April 8, 1980Assignee: American Cyanamid CompanyInventor: Allan Wissner
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Patent number: 4196215Abstract: Alkyne compounds of the formula ##STR1## wherein R.sup.1 is H, alkyl of up to 4 carbon atoms or phenyl; R.sup.2 is H, aliphatic acyl of up to 6 carbon atoms or aroyl of up to 11 carbon atoms; R.sup.3 and R.sup.4 are H, F, Cl or Br and n is 0 or 1, and physiologically acceptable metals salts thereof, have anti-inflammatory activity. These compounds can be made from compounds of the formula ##STR2## wherein Q is a functionally-modified hydroxy and R.sup.1, R.sup.3, R.sup.4 and n are as above by treatment with a solvolyzing agent.Type: GrantFiled: June 28, 1978Date of Patent: April 1, 1980Assignee: Merck Patent Gesellschaft mit beschraenkter HaftungInventors: Joachim Gante, Hans-Adolf Kurmeier, Dieter Orth, Erich Schacht, Albrecht Wild
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Patent number: 4194010Abstract: Acetals, enol acylates and enol ethers of the compound of the compound of the formula (I): ##STR1## notionally derivable from a C.sub.1-8 alcohol or C.sub.1-8 acid are useful anti-inflammatory agents.Type: GrantFiled: June 2, 1978Date of Patent: March 18, 1980Assignee: Beecham Group LimitedInventor: Alexander C. Goudie
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Patent number: 4193931Abstract: Novel 7-(substituted indanyl or naphthyl)-3-methyl-octa-2,4,6-triene derivatives useful as anti-tumor agents are disclosed.Type: GrantFiled: April 24, 1978Date of Patent: March 18, 1980Assignee: Hoffmann-La Roche Inc.Inventor: Peter Loeliger
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Patent number: 4190602Abstract: Monoacetals of aromatic diketones in which the acetal group is derived from primary mono- or dialkohols are useful as sensitizers in the photochemical polymerization or photochemical crosslinking of polymers. They are prepared from the diketones (benzils) by reaction with sulfites. The sulfites and the benzils may be formed immediately before the reaction in the same vessel without isolating these compounds. Most of the benzil monoacetals are new compounds.Type: GrantFiled: June 22, 1978Date of Patent: February 26, 1980Assignee: Ciba-Geigy CorporationInventors: Jean Brunisholz, Rudolf Kirchmayr
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Patent number: 4189409Abstract: A novel process is provided for preparing a methylenebis(2-hydroxy-4-alkoxybenzophenone), comprising forming a novel 2-hydroxy-4-alkoxyacyloxymethylbenzophenone by a reaction of a 2-hydroxy-4-alkoxybenzophenone with a carboxylic acid and formaldehyde, and causing the 2-hydroxy-4-alkoxyacyloxymethylbenzophenone to react with a 2-hydroxy-4-alkoxybenzophenone in the presence of an acid catalyst.Both the acyloxymethylhydroxyalkoxybenzophenone and methylenebis(2-hydroxy-4-alkoxybenxophenone) which are prepared according to this invention are useful to prevent-degradation of organic materials, particularly as light stabilizers for synthetic resins.Type: GrantFiled: July 14, 1978Date of Patent: February 19, 1980Assignee: Argus Chemical CorporationInventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata
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Patent number: 4188495Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl of 1 to 5 carbon atoms or --CO--(CH.sub.2).sub.p --NR'R" wherein p is 0 or an integer from 1 to 4; each of R' and R" when taken individually is hydrogen or alkyl of 1 to 4 carbon atoms; R' and R" when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrollo, pyrrolidino, morpholino and N-alkylpiperazino having from 1 to 4 carbon atoms in the alkyl group;R.sub.2 is selected from hydrogen, alkanoyl of 1 to 6 carbon atoms and benzoyl;R.sub.3 is selected from hydrogen, methyl and ethyl;R.sub.4 is selected from hydrogen, alkyl of 1 to 6 carbon atoms and benzyl;Z is selected from:(a) alkylene having from one to nine carbon atoms;(b) --(alk.sub.1).sub.m --X--(alk.sub.2).sub.n -- wherein each of (alk.sub.1) and (alk.sub.2) is alkylene having from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.Type: GrantFiled: November 14, 1977Date of Patent: February 12, 1980Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4188491Abstract: A process is disclosed for preparing arylpropionic acids of formula Ar--CH(CH.sub.3)--COOH, by reacting an aryl Grignard reagent with a metal pyruvate or with a pyruvamide, to form a hydroxy acid of formula Ar--C(OH)(CH.sub.3)--COOH or its amide, and converting the acid or amide to the product.Type: GrantFiled: March 24, 1978Date of Patent: February 12, 1980Assignee: The Boots Company LimitedInventors: John S. Nicholson, John L. Turner
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Patent number: 4186142Abstract: Novel cyclization substrates of the formula: ##STR1## wherein: (a) R.sub.1 is H or alkyl of one to four carbons;(b) R.sub.2 is H or alkyl of one to four carbons, with the proviso that R.sub.1 is H when R.sub.2 is alkyl; and with the proviso that P.sub.2 is H when R.sub.1 is alkyl;(c) R.sub.3 is a leaving group selected from the group consisting of OH, alkoxy of one to four carbons, alkoxyalkyoxy of from two to about four carbons, acyloxy of from about one to about seven carbons, and trialkylsilyloxy;(d) R.sub.4 is halogen, alkoxy of from one to four carbons, hydrocarbyl of from one to about four carbons, hydrocarbyl of from one to about four carbons substituted by one or more (1) halogens or (2) alkoxy moieties of from one to two carbons; and(e) R.sub.5 is H, alkyl of one to six carbons, hydroxy, or an esterified or estherified moiety of (1) less than eight carbons selected from the group consisting of alkoxy, trialkylsilyloxy, aralkyloxy, cyclo-alkoxy, and heterocyclo-oxy radicals; (2) .alpha.Type: GrantFiled: February 22, 1978Date of Patent: January 29, 1980Assignee: Akzona IncorporatedInventors: Filippus J. Zeelen, Marinus B. Groen
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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: 4180585Abstract: Acetals, enol acylates and enol ethers of the compound of the compound of the formula (I): ##STR1## notionally derivable from a C.sub.1-8 alcohol or C.sub.1-8 acid are useful anti-inflammatory agents.Type: GrantFiled: October 26, 1976Date of Patent: December 25, 1979Assignee: Beecham Group LimitedInventor: Alexander C. Goudie
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Patent number: 4178381Abstract: C-homoestratrienes of the formula ##STR1## wherein ##STR2## R.sub.1 and R.sub.2 are the same or different, and each is hydrogen, acyl, alkyl, cycloalkyl or tetrahydropyranyl; andR.sub.3 is hydrogen, ethynyl or chloroethynyl; possess very good estrogenic properties.Type: GrantFiled: December 4, 1978Date of Patent: December 11, 1979Assignee: Schering, AktiengesellschaftInventors: Gregor Haffer, Ulrich Eder, Gerhard Sauer, Rudolf Wiechert, Yukishige Nishino, Gunter Neef
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Patent number: 4172839Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.2 series.Type: GrantFiled: December 8, 1977Date of Patent: October 30, 1979Assignee: American Cyanamid CompanyInventor: Allan Wissner
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Patent number: 4170597Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the E.sub.2 series.Type: GrantFiled: December 8, 1977Date of Patent: October 9, 1979Assignee: American Cyanamid CompanyInventor: Allan Wissner
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Patent number: 4159991Abstract: .alpha.-Acyloxy-N,N'-diacylmalonamides of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are the same or different and are hydrogen, straight chain or branched alkyl radicals having from one to eleven carbon atoms, or hydrocarbon radicals with six to twelve carbon atoms and comprising at least one aromatic ring, are novel compounds prepared by the action of a mixture of carboxylic acids R.sub.3 COOH and R.sub.4 COOH upon an .alpha.-acyloxymalononitrile, R.sub.1 COO--C(CN).sub.2 --R.sub.2, in the presence of an acid catalyst and are useful as intermediates in organic synthesis and low temperature activators in bleaching or scouring compositions.Type: GrantFiled: August 22, 1977Date of Patent: July 3, 1979Assignee: Produits Chimiques Ugine KuhlmannInventors: Bernard Dubreux, Serve Y. Delavarenne, Jean-Pierre Schirmann
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Patent number: 4156694Abstract: The present invention relates to novel benzo(b) bicyclo[3.3.1]nones of the general formula I: ##STR1## and a salt or nitrogen oxide thereof, in which R.sub.1 and R.sub.2 stand for hydrogen, alkyl of 1-6 carbon atoms, alkenyl of 1-6 carbon atoms, an optionally substituted aralkyl group or an acyl group orR.sub.1 and R.sub.2 together with the nitrogen atom represent a heterocyclic 5- or 6-membered ringR.sub.3 is a free, etherified or esterified hydroxy,X and Y stand for hydrogen, hydroxy, halogen, alkyl or alkoxy of 1-6 C-atoms, nitro, CF.sub.3 or an acyloxy group, having valuable biological activities, particularly anorectic activity.Type: GrantFiled: December 30, 1977Date of Patent: May 29, 1979Assignee: Akzona IncorporatedInventors: Colin L. Hewett, David S. Savage, James Redpath, Thomas Sleigh, Duncan R. Rae
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Patent number: 4146385Abstract: The invention provides novel phenoxyalkylcarboxylic acids which are useful in therapy as metabolic regulators and in agriculture as selective herbicides.Type: GrantFiled: August 16, 1976Date of Patent: March 27, 1979Assignee: Societe de Recherches Industrielles S.O.R.I.Inventor: Bernard Majoie
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Patent number: 4145557Abstract: Novel 3-phenoxyphenylalkyl amines and the amides, alcohols, tetrazoles, and carbamates related thereto as well as novel intermediates useful in the preparation of such compounds. The compounds of this invention are useful as anti-inflammatory, analgesic, and antipyretic agents.Type: GrantFiled: February 14, 1977Date of Patent: March 20, 1979Assignee: Eli Lilly and CompanyInventor: Winston S. Marshall
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Patent number: 4136200Abstract: Phenylbutanol derivatives of the formula Z-C(CH.sub.3) (OH)-CH.sub.2 -Y wherein Z is 4-biphenyl or 4-phenoxyphenyl wherein the phenoxy group is unsubstituted or substituted by F, Cl or Br and Y is COOR.sup.2 or CH.sub.2 OR.sup.3 wherein R.sup.2 is H or alkyl of 1 to 6 carbon atoms and R.sup.3 is H or alkanoyl of 1 to 6 carbon atoms, and their physiologically acceptable salts, possess anti-inflammatory activity and are produced by (a) treating with a solvolyzing agent a compound of the formula Z-C(CH.sub.3) (OH)-CH.sub.2 -W or Z-CX(CH.sub.3)-CH.sub.Type: GrantFiled: June 28, 1977Date of Patent: January 23, 1979Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Erich Schacht, Werner Mehrhof, Albrecht Wild, Joachim Gante, Hans-Adolf Kurmeier
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Patent number: 4131746Abstract: (dl)-13-Substituted sulfinyl-prostaglandin-like [(dl)-2.alpha.-substituted-3.beta.-(1.alpha.-substituted sulfinyl-trans-2-alkenyl)-1-oxygenated cyclopentane and (dl)-2.alpha.-substituted-3.beta.-(1.alpha.-substituted sulfinyl-trans-2-alkenyl)-4-oxygenated-1-oxygenated cyclopentane] compounds exhibit prostaglandin-like biological properties and are also useful intermediates in the preparation of known prostaglandins.Type: GrantFiled: January 7, 1977Date of Patent: December 26, 1978Assignee: Syntex (USA) Inc.Inventors: Karl G. Untch, Gilbert J. Stork
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Patent number: 4124623Abstract: Prostaglandin analogs with the following cyclopentane ring structure: ##STR1## are disclosed along with intermediates useful in their preparation and processes for their preparation. These analogs are useful for some of the same pharamcological purposes as the prostaglandins, particularly and especially as blood platelet aggregation inhibitors.Type: GrantFiled: June 23, 1977Date of Patent: November 7, 1978Assignee: The Upjohn CompanyInventor: David C. Peterson
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Patent number: 4117234Abstract: Estrogenic steroids are synthesized by combining under conditions favoring the formation of a trans-olefin, a .gamma.-arylpropanal with a 5,5,8,8-tetraalkoxy Wittig reagent. After hydrolysis of the gem-diethers, the resulting dioxo is internally condensed to form a cyclopentenone. The ketone is reduced to an oxy group and the resulting 2-(6'-arylhex-3'-enyl-1)cyclopent-2-en-1-ol or derivative thereof is cyclized to the .DELTA..sup.13,17 -estrene, preferably 17-alkyl-.DELTA..sup.13,17 -estrene with the A ring aromatized. After epoxidation, the 17-alkyl derivative is rearranged to form the 13-alkyl-1,3,5(10)-estratien-17-one. New compounds are provided as intermediates and final products.Type: GrantFiled: September 24, 1976Date of Patent: September 26, 1978Assignee: The Board of Trustees of the Leland Stanford Junior UniversityInventors: William S. Johnson, Paul A. Bartlett
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Patent number: 4116981Abstract: There is provided a novel method of synthesizing certain tetracyclic quinones. In particular, there is provided a novel route to the synthesis of (+)-7-deoxydaunomycinone and analogs thereof which includes the provision of novel tetrahydronaphthoquinones and tetracyclic quinone intermediates. The compounds of the present invention are provided through a route comprising a Diels-Alder addition of certain isobenzofurans to certain novel tetrahydronaphthoquinones. The products of the synthetic route provided herein may be converted into compounds of known antibiotic and antineoplastic activity.Type: GrantFiled: May 2, 1977Date of Patent: September 26, 1978Assignees: Yuh-Geng Tsay, Research CorporationInventor: Andrew S. Kende
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Patent number: 4115456Abstract: Alkyne compounds of the formula ##STR1## wherein R.sup.1 is H, alkyl of up to 4 carbon atoms or phenyl; R.sup.2 is H, aliphatic acyl of up to 6 carbon atoms or aroyl of up to 11 carbon atoms; R.sup.3 and R.sup.4 are H, F, Cl or Br and n is 0 or 1, and physiologicaly acceptable metals salts thereof, have antiinflammatory activity. These compounds can be made from compounds of the formula ##STR2## wherein Q is a functionally-modified hydroxy and R.sup.1, R.sup.3, R.sup.4 and n are as above by treatment with a solvolyzing agent.Type: GrantFiled: June 18, 1976Date of Patent: September 19, 1978Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Joachim Gante, Hans-Adolf Kurmeier, Dieter Orth, Erich Schacht, Albrecht Wild
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Patent number: 4107197Abstract: Described are .alpha.-oxy(oxo) sulfides and ethers having the generic structure: ##STR1## wherein X is one of: ##STR2## Z is one of sulfur or oxygen; when R.sub.1 and R.sub.2 are taken separately, R.sub.1 is hydrogen or methyl, and R.sub.2 is methyl; and when R.sub.1 and R.sub.2 are taken together, R.sub.1 and R.sub.2 form phenyl moieties; and Y is one of C.sub.1 -C.sub.4 alkyl, C.sub.3 or C.sub.4 alkenyl, acetyl, methoxycarbonylmethyl, or 1,3-diethylacetonyl.Addition of one or more .alpha.Type: GrantFiled: March 31, 1977Date of Patent: August 15, 1978Assignee: International Flavors & Fragrances Inc.Inventors: William J. Evers, Howard H. Heinsohn, Jr.