Ring Nitrogen Is Shared By Five-membered Cyclo And Six-membered Cyclo (e.g., Vincamine, Etc.) Patents (Class 546/51)
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Patent number: 4432982Abstract: The invention relates to new polycyclic compounds substituted on the A-ring. More particularly, the invention concerns new polycyclic compounds of the formula (I) ##STR1## wherein R.sup.1 is methoxy or halogen andR.sup.2 is hydrogen; orR.sup.1 is hydrogen andR.sup.2 is halogen and acid addition salts thereof.Type: GrantFiled: February 4, 1982Date of Patent: February 21, 1984Assignee: Richter Gedeon Vegyeszeti Gyar Rt.Inventors: Csaba Szantay, Lajos Szabo, Gyorgy Kalaus, Mari Zajer nee Balazs, Lilla Forgach, Egon Karpati, Arpad Kiraly, Gyongyver Kiraly nee Soos, Laszlo Szporny, Bela Rosdy
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Patent number: 4424224Abstract: The invention relates to the new apovincaminol-3',4',5'-trimethoxy-benzoate and acid addition salts thereof.The new compound may be prepared by reacting apovincaminol or an acid addition salt thereof with 3,4,5-trimethoxy benzoic acid or a reactive derivative thereof capable of acylation and if desired converting the compound thus obtained into an acid addition salt.The new compound of the present invention can be used in therapy in the treatment of skin diseases attached to pathological cell proliferation and in the propylaxis of such diseases.Type: GrantFiled: February 4, 1982Date of Patent: January 3, 1984Assignee: Richter Gedeon Vegyeszeti Gyar RtInventors: Csaba Szantay, Lajos Szabo, Gyorgy Kalaus, Zsuzsanna Gyulai, Maria Zajer nee Balazs, Lilla Forgach, Egon Karpati, Arpad Kiraly, Gyongyver Kiraly nee Soos, Laszlo Szporny, Bela Rosdy
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Patent number: 4424223Abstract: The invention relates to the new 17,18-dehydro-apovincaminol-3',4',5'-trimethoxy-benzoate of formula (I) ##STR1## and acid addition salts thereof. According to another aspect of the invention there is provided a process for the preparation of these new compounds. Still another aspect of the invention is a pharmaceutical composition for treating psoriasis.Type: GrantFiled: February 4, 1982Date of Patent: January 3, 1984Assignee: Richter Gedeon Vegyeszeti Gyar RTInventors: Tibor Keve, Bela Zsadon, Gyorgy Fekete, Csaba Lorincz, Janos Galambos, Maria Zajer nee Balazs, Lilla Forgach, Egon Karpati, Arpad Kiraly, Gyongyver Kiraly nee Soos, Laszlo Szporny, Bela Rosdy
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Patent number: 4419359Abstract: The present invention relates to the compounds of the Formulae 1a and 1b and pharmaceutically acceptable acid addition salts thereof.The new 9-nitro-apovincaminol-3',4',5'-trimethoxybenzoate of the Formula 1a ##STR1## and the 11-nitro-apovincaminol-3',4',5'-trimethoxy-benzoate of the Formula 1b ##STR2## and pharmaceutically acceptable acid addition salts thereof can be prepared by nitrating the apovincaminol-3',4',5'-trimethoxy-benzoate of the Formula 11, ##STR3## if desired separating the mixture of the compounds of the Formulae 1a and 1b thus obtained into its components, if desired converting a compound of the Formula 1a or 1b thus obtained into pharmaceutically acceptable acid addition salts thereof.The new compounds of the present invention can be used in therapy in the treatment of psoriasis.Type: GrantFiled: February 4, 1982Date of Patent: December 6, 1983Assignee: Richter Gedeon Vegyeszeti Gyar RTInventors: Tibor Keve, Gyorgy Fekete, Csaba Lorincz, Janos Galambos, Bela Zsadon, Maria Zajer nee Balazs, Lilla Forgach, Egon Karpati, Arpad Kiraly, Gyongyver Kiraly nee Soos, Laszlo Szporny, Bela Rosdy
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Patent number: 4400514Abstract: The invention concerns a new process for the preparation of apovincaminic acid ester derivatives of the general formula (I) ##STR1## wherein R.sup.1 and R.sup.2 independently represent an alkyl group having 1 to 6 carbon atoms,and pharmaceutically acceptable salts thereof.According to the invention the apovincaminic acid ester derivatives of the general formula (I) are prepared by reacting the corresponding 9- and/or 10- and/or 11-halo-14-oxo-15-hydroxyimino-E-homo-eburnane derivatives with an alkanol of the general formula R.sup.1 --OH, wherein R.sup.1 is as defined above, and with a dehydrating concentrated acid, and subsequently reducing the 9- and/or 10- and/or 11-halo-apovincaminic acid esters obtained, selectively on the aromatic ring. Alternatively, the 9- and/or 10- and/or 11-halo-apovincaminic acid esters can also be used as starting materials.Type: GrantFiled: November 21, 1980Date of Patent: August 23, 1983Assignee: Richter Gedeon Vegyeszeti Gyar Rt.Inventors: Csaba Szantay, Lajos Szabo, Gyorgy Kalaus, Lajos Dancsi, Tibor Keve, Ferenc Drexler, Krisztina Mihalyfi
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Patent number: 4382936Abstract: A compound of the formula: ##STR1## wherein R.sup.1 is a C.sub.1 -C.sub.6 alkyl group and R is a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group, and their salts, which are useful as cerebral vasodilator; and a compound of the formula: ##STR2## wherein R.sup.2 is a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group, R.sup.3 is a hydrogen atom or the formula: --CO.sub.2 R.sup.1 (R.sup.1 is a C.sub.1 -C.sub.6 alkyl group) and W is an oxygen atom, an imino group or ##STR3## but not an imino group in case that R.sup.3 is a hydrogen atom, which are intermediates of the compound (I), useful per se as cerebral vasodilator and/or antihypertensive agents.Type: GrantFiled: April 30, 1981Date of Patent: May 10, 1983Assignee: Sumitomo Chemical Company, LimitedInventors: Junki Katsube, Keiichi Ono, Hajime Kawakami
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Patent number: 4379935Abstract: A process is taught for the synthesis of vincamine and related indole alkaloids, according to which, through only two steps and through a novel synthesis intermediate, namely the glycidic ester, having the formula ##STR1## wherein R" represents --COOCH.sub.3 or --COOCH.sub.2 CH.sub.3, 1-ethyl-1,2,3,4,5,6,7,12b-octahydroindole[2,3-a]quinolizine-1-carboxaldehy de is reacted with a haloester in the presence of a base and the glycidic ester is converted to vincamine or apovincamine or like esters by reaction with a Lewis acid or a mineral acid, the reaction products being subsequently separated by chromatography.Type: GrantFiled: July 30, 1981Date of Patent: April 12, 1983Assignee: Paolo Corvi MoraInventors: Silvano Paracchini, Paolo C. Mora
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Patent number: 4366157Abstract: A compound of the formula, ##STR1## wherein R.sup.1 is C.sub.1 -C.sub.6 alkyl group and R.sup.2 is aryl group, which is a medicine useful to treat cerebral arteriosclerosis, senile mental indolence and cerebral insufficiency.Type: GrantFiled: July 27, 1981Date of Patent: December 28, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Keiichi Ono, Hajime Kawakami, Junki Katsube
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Patent number: 4364947Abstract: This invention relates to novel vincamine derivatives useful as cerebral metabolic and circulatory regulators. The compounds have the following structural formula: ##STR1## wherein R.sub.1 is hydrogen or a hydroxyl group and R.sub.2 is an alkyl group.Type: GrantFiled: May 8, 1981Date of Patent: December 21, 1982Assignee: Nippon Zoki Pharmaceutical Co., Ltd.Inventor: Yoshio Toyomaki
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Patent number: 4362730Abstract: Vincamine saccharinate, a novel derivative of vincamine, and pharmaceutical compositions containing vincamine saccharinate are disclosed. The solubility of vincamine saccharinate in glycerol-ethanol mixtures and the superior taste characteristics of vincamine saccharinate allow the preparation of preferred pharmaceutical compositions in solution form which are suitable for oral administration, especially in the form of drops.Type: GrantFiled: July 16, 1981Date of Patent: December 7, 1982Assignee: Heinrich Mack Nachf. Chem-Pharm. FabrikInventors: Kurt Rader, Peter Stoss
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Patent number: 4356305Abstract: The invention relates to new halovincamone derivatives of the general formula (I), ##STR1## wherein R is a C.sub.1-6 alkyl group and X is halogen, and pharmaceutically acceptable acid addition salts and optically active isomers thereof. These compounds possess valuable vasodilating effect, and can be applied to advantage in the therapy.The new compounds defined above are prepared according to the invention so that a single epimer or an epimeric mixture of a racemic or optically active halogenated 14-oxo-15-hydroxy-E-homoeburnane derivative of the general formula (II), ##STR2## wherein R and X are as defined above, or an acid addition salt thereof is treated with an oxidizing agent, and, if desired, the resulting compound of the general formula (I) is converted into its pharmaceutically acceptable acid addition salt and/or resolved.Type: GrantFiled: August 5, 1980Date of Patent: October 26, 1982Assignee: Richter Gedeon Vegyeszeti Gyar Rt.Inventors: Csaba Szantay, Lajos Szabo, Gyorgy Kalaus, Lajos Dancsi, Tibor Keve, Ferenc Drexler
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Patent number: 4347249Abstract: The invention relates to new chemical compounds.They are compounds corresponding to formula Ia. ##STR1## in which: R'.sub.3 represents a hydrogen atom or a hydroxy radical; R'.sub.5 represents a hydrogen atom or a hydroxy radical; or R'.sub.3 and R'.sub.5 together represent an epoxy bridge or a double bond; R".sub.5 represents a hydrogen atom or an ethyl radical; R'.sub.7 and R'.sub.8 are the same or different and represent a hydrogen atom or a methyl, hydroxymethylene, alkoxymethylene, aryloxymethylene, aminomethylene, monoalkyl or dialkyl aminomethylene, acylmethylene, arylaminomethylene, hydroxyethyl aminomethylene, alkylthiomethylene, aryloxythiomethylene or cyanomethylene radical; R.sub.1 represents a hydrogen atom or an alkyl, formyl or acyl radical: R.sub.2 represents a hydrogen atom or an alkoxy radical; R.sub.7 represents an alkanoyloxy radical, the broken line representing an optional double bond.These compounds can be used as drugs.Type: GrantFiled: July 9, 1980Date of Patent: August 31, 1982Assignee: Agence Nationale de Valorisation de la Recherche (ANVAR)Inventors: Pierre Potier, Nicole Langlois, Yves Langlois, Ratremaniaina Z. Andriamialisoa, Pierre Mangeney
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Patent number: 4345082Abstract: The invention relates to new hydroxyamino-eburnane derivatives of the general formula (I), ##STR1## wherein R.sup.1 and R.sup.2 each stand for a C.sub.1-6 alkyl group, as well as to pharmaceutically acceptable acid addition salts and optically active isomers of these compounds.These new compounds can be applied as peripheral vasodilatating agents or can be converted into other compounds, e.g. vincamine and apovincamine derivatives of valuable therapeutical effects.The compounds of the general formula (I) are prepared according to the invention by reacting a hexahydro-indoloquinolisinium derivative of the general formula (II), ##STR2## wherein R.sup.2 is as defined above and X stands for an acid residue, with a methylenemalonic acid diester derivative of the general formula (III), ##STR3## wherein R.sup.Type: GrantFiled: May 29, 1980Date of Patent: August 17, 1982Assignee: Richter Gedeon Vegyeszeti Gyar Rt.Inventors: Csaba Szantay, Lajos Szabo, Gyorgy Kalaus, Janos Sapi, Lajos Dancsi, Tibor Keve, Maria Gazdac
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Patent number: 4316028Abstract: A compound of the formula: ##STR1## wherein R.sup.1 is a C.sub.1 -C.sub.6 alkyl group and R is a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group, and their salts, which are useful as cerebral vasodilator; and a compound of the formula: ##STR2## wherein R.sup.2 is a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group, R.sup.3 is a hydrogen atom or the formula: --CO.sub.2 R.sup.1 (R.sup.1 is a C.sub.1 -C.sub.6 alkyl group) and W is an oxygen atom, an imino group or ##STR3## but not an imino group in case that R.sup.3 is a hydrogen atom, which are intermediates of the compound (I), useful per se as cerebral vasodilator and/or antihypertensive agents.Type: GrantFiled: November 13, 1979Date of Patent: February 16, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Junki Katsube, Keiichi Ono, Hajime Kawakami
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Patent number: 4316029Abstract: Vincaminic acid derivatives of formula (A) ##STR1## useful in treating cerebral insufficiency, are prepared by reacting 1-ethyl-2,3,4,6,7,12-hexahydroindolo[2,3-a]quinolizine with the 2,4-DNP hydrazone of ethyl or methyl bromopyruvate followed by (i) reduction of the C.dbd.N bond and (ii) simultaneous cyclization with removal of the ketone-protecting group in either order.Type: GrantFiled: June 20, 1980Date of Patent: February 16, 1982Assignee: SynthelaboInventor: Guy Rossey
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Patent number: 4315011Abstract: The invention is directed to 1-alkyl-9-bromohexagydro indoloquinolizium salts and a method for their use to increase blood circulation and decrease in blood vessel resistance.Type: GrantFiled: July 10, 1979Date of Patent: February 9, 1982Assignee: Richter Gedeon Vegyeszeti Gyar Rt.Inventors: Csaba Szantay, Lajos Szabo, Gyoorgy Kalaus, Lajos Dancsi, Tibor Keve, Egon Karpati, Laszlo Szporny
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Patent number: 4307100Abstract: Compounds with antitumoral activity corresponding to the formula (I): ##STR1## wherein R'.sub.1 is a hydrogen atom or an alkoxy, acyl, formyl or haloacyl radical; R'.sub.2 is a hydrogen atom or an alkyl radical; R'.sub.3 and R".sub.3 are a hydrogen atom, hydroxyl radical or an alkanoyloxy radical, and together are a carbonyl group, and R'.sub.3 and R'.sub.5 together are an epoxy bridge or a double bond; R'.sub.4 is a hydrogen atom or an alkyloxycarbonyl, hydroxymethyl, alkanoyloxymethyl or acetamido radical; R'.sub.5 and R".sub.5 are a hydrogen atom or a hydroxyl, alkanoyloxyl, ethyl or 2-hydroxyethyl radical; R'.sub.6 is a hydrogen atom or an ethyl, 2-hydroxyethyl or acetyl radical; R.sub.1 is a hydrogen atom or an alkyl, formyl or acyl radical; R.sub.2 is a hydrogen atom or alkoxy radical; R.sub.3 is a hydrogen atom or a hydroxyl or alkanoyloxyl radical, and together with R.sub.4 is an epoxy bridge or a double bond; R.sub.4 is a hydrogen atom or a hydroxyl, alkanoyloxyl radical, and together with R.sub.Type: GrantFiled: August 20, 1979Date of Patent: December 22, 1981Assignee: Agence Nationale de Valorisation de la Recherche (ANVAR)Inventors: Nicole Langlois, Yves Langlois, Ratremaniaina Z. Andriamialisoa, Pierre Potieo, Pierre Mangeney
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Patent number: 4291038Abstract: New 20,21-dinoreburnamenine derivatives are disclosed which have the formula I ##STR1## wherein the hydroxyl in the 14-position of the molecule is in either of the two possible positions at the carbon atom in the 14-position to which the isomers A and B correspond and the hydrogens in the 3-position and the 16-position of the molecule are in cis- or in trans-position to each other, and their pharmaceutically acceptable acid addition salts, as well as pharmaceutical formulations thereof.The new compounds of formula I are prepared by reducing the corresponding 14-oxoderivatives. They are effective in favorably influencing the cerebral vascular circulation.Type: GrantFiled: April 7, 1980Date of Patent: September 22, 1981Assignee: Roussel UclafInventors: Andre Farcilli, Italo Medici, Robert Fournex, Fernando Barzaghi
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Patent number: 4285949Abstract: The new derivatives of vincamine according to this invention may be represented by the general formula ##STR1## in which R.sub.1 represents a halogen atom and R.sub.2 may represent a hydroxy group whereas R.sub.3 may represent a hydrogen atom, or R.sub.2 may form with R.sub.3 an additional bond.The compounds may be used to treat cardio-circulatory, cerebro-vascular and respiratory insufficiencies.Type: GrantFiled: December 11, 1978Date of Patent: August 25, 1981Assignee: Omnichem Societe AnonymeInventor: Jean A. A. J. Hannart
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Patent number: 4283536Abstract: This invention relates to the preparation of vincadifformine and related derivatives which are useful as starting material for the synthesis of among other alkaloids vincamine and other similar compounds possessing interesting psychopharmacologic properties.A tetrahydro-.beta.-carboline (II) is reacted with benzoyl chloride to provide a 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido-(3,4-b)-indole (III). Then compound (III) is reduced to give a 2-benzyl-1,2,3,4-tetrahydro-9H-pyrido-(3,4-b)-indole (IV). Thereafter, compound (IV) is transformed by t-butyl hypochlorite into a chloroindolenine derivative (V) which is immediately treated with a metal dialkylmalonate such as thallium t-butyl methyl malonate to give a dialkyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino-(4,5-b)-indole-5,5-dicarboxylate (VI). Compound (VI) is then partly decarboxylated into a alkyl 3-benzyl-1,2,3,4,5,6-hexahydro-(4,5-b) indole-5-carboxylate (VII).Type: GrantFiled: April 30, 1979Date of Patent: August 11, 1981Assignee: University of VermontInventor: Martin E. Kuehne
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Patent number: 4283401Abstract: A novel process for preparing 11-bromo-vincaminic acid esters of the general formula ##STR1## wherein R.sup.1 and R.sup.2 each stand independently from each other for a C.sub.1-6 alkyl group, comprising the steps of treating a 1-alkyl-1-alkoxycarbonylethyl-octahydroindolo-quinolisine of the general formula ##STR2## wherein R.sup.2 is as defined above and R.sup.3 stands for a C.sub.1-6 alkyl group, with a brominating agent and treating the resulting isomeric mixture of the bromo-derivatives with an alkaline agent or treating the corresponding 14-oxo-E-homo-eburnane being unsubstituted in ring A with a brominating agent and nitrosating the resulting 11-bromo-14-oxo-E-homo-eburnane of the general formula ##STR3## wherein R.sup.2 is as defined above, then subjecting the resulting 11-bromo-14-oxo-15-hydroxyimino-E-homoeburnanes to deoxyimination and treating the 14,15-dioxo-derivatives obtained with a base in an alcohol of the general formula R.sup.1 OH, wherein R.sup.1 is as defined above.Type: GrantFiled: July 11, 1979Date of Patent: August 11, 1981Assignee: Richter Gedeon Vegyeszeti Gyar RTInventors: Csaba Szantay, Lajos Szabo, Gyorgy Kalaus, Lajos Dancsi, Tibor Keve, Egon Karpati, Laszlo Szporny
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Patent number: 4278682Abstract: Vasodilating octahydro-indolo[2,3-a]quinolizine derivatives of the formula ##STR1## wherein Q is hydrogen or an A--CH.sub.2 --CH.sub.2 -- group and A is cyano or --COOR, wherein R is C.sub.1-6 alkyl.Type: GrantFiled: April 2, 1979Date of Patent: July 14, 1981Assignee: Richter Gedeon Vegyeszeti Gyar Rt.Inventors: Csaba Szantay, Lajos Szabo, Gyorgy Kalaus, Egon Karpati, Laszlo Szporny
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Patent number: 4267330Abstract: This invention relates to the preparation of vincadifformine and related derivatives which are useful as starting material for the synthesis of vincamine and other related compounds possessing interesting psychopharmacologic properties.A N-benzyl-tetrahydro-.gamma.-carboline compound (III) is halogenated with t-butyl hypochlorite to obtain a haloindolenine compound which is directly treated with a metal dialkyl malonate such as thallium dialkyl malonate to provide a dialkyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino (4,5-b) indole-5,5-dicarboxylate compound, said latter compound being hydrogenated to provide a dialkyl 1,2,3,4,5,6 hexahydroazepino (4,5-b) indole-5,5-dicarboxylate, said latter compound being condensed with a functionalized aldehyde, typically a haloaldehyde, to provide vincadifformine or a related derivative by passing through an intermediate compound being a salt of a dialkyl 3,3-(alkenyl)-1,2,3,4,5,6-hexahydroazepino(4,5-b) indolinium-(5,5)-dicarboxylate.Type: GrantFiled: August 24, 1978Date of Patent: May 12, 1981Assignee: Omnium Chimique Societe AnonymeInventor: Martin E. Kuehne
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Patent number: 4220774Abstract: The preparation of vincadifformine and some derivatives thereof for use as a starting material for synthesis of the corresponding vincamine derivatives or for synthesis of bisindole alkaloids having clinically important antitumor properties.Type: GrantFiled: October 26, 1978Date of Patent: September 2, 1980Assignee: Omnium ChimiqueInventor: Martin E. Kuehne
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Patent number: 4210584Abstract: Vindesine is prepared by converting 4-desacetyl VLB C-3 carboxhydrazide to the corresponding azide with a nitrite such as n-butyl nitrite in THF and then reacting the thus formed azide with triphenylphosphine to yield an intermediate acyl iminophosphorane, which compound is decomposed with acid to yield vindesine of high purity and in good yield.Type: GrantFiled: January 15, 1979Date of Patent: July 1, 1980Assignee: Eli Lilly and CompanyInventors: Gloria C. Paschal, Gerald L. Thompson
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Patent number: 4190658Abstract: Novel eburnamenine derivatives of the formula ##STR1## in the form of racemic mixtures or optically active isomers and their non-toxic, pharmaceutically acceptable acid addition salts which are oxygenators and cerebral vasoregulators of great value.Type: GrantFiled: July 17, 1978Date of Patent: February 26, 1980Assignee: Roussel UclafInventors: Julien Warnant, Andre Farcilli, Italo Medici
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Patent number: 4172077Abstract: Tumor inhibiting alkaloids are recovered from Vinca Rosea L. by a method which comprises extracting the dried leaves with a solvent selected from the group consisting of an alkanol having 1 to 5 carbon atoms, a mixture of an alkanol having 1 to 5 carbon atoms and a dilute, aqueous solution, benzene and benzene homologs; subsequently purifying the alkaloid extract obtained by a phase-change method between immiscible solvents, precipitating the main amount of dimeric alkaloids in form of their sulphuric acid addition salts, isolating leurosine, vincistine, vinblastine, desacetoxy-vinblastine, N-desmethyl-vinblastine and desacetyl-vinblastine from the salt mixture obtained, and then completing the separation and isolation of the remaining alkaloids by separation and isolation by adjusting the pH-value of the mother liquor, after precipitation and removal of the salt mixture, to 5.Type: GrantFiled: May 22, 1978Date of Patent: October 23, 1979Assignee: Richter Gedeon Vegyeszeti Gyar RTInventors: Karola Jovanovics, Gyorgy Fekete, Eszter Dezseri, Lajos Dancsi, Csaba Lorincz, Bela Szarvady, Gyorgy Dobo, Csaba Szantay, Lajos Szabo
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Patent number: 4167506Abstract: A group of novel polynuclear heterocyclic compounds having a diazaphenalene skeleton. These compounds assume orange to reddish violet colors according to the types of substituents on the diazaphenalene skeleton, and have excellent thermal stability and weatherability and good dispersibility in polymeric materials. They are useful as orange to reddish violet pigments, especially for coloring polymeric materials.Type: GrantFiled: September 13, 1977Date of Patent: September 11, 1979Assignee: Teijin LimitedInventors: Keizo Shimada, Toshiaki Harada, Masahiro Koga, Shizuo Nagahama, Hiroyoshi Minematsu, Hidetsugu Yoshida
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Patent number: 4163851Abstract: The new compound vincane of the formula ##STR1## is prepared by the reduction or reductive dehydratation, respectively, a compound of the formula ##STR2## wherein A.about.B represents the group --CH.dbd.CH-- or ##STR3## i.e. of vincamenine or of vincanol.Type: GrantFiled: July 6, 1977Date of Patent: August 7, 1979Assignee: Richter Gedeon Vegyeszeti Gyar RTInventors: Otto Clauder, Arpad Kiraly, Jozsef Kokosi, Egon Karpati, Laszlo Szporny
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Patent number: 4159269Abstract: 3-Spiro-5"-oxazolidine-2",4"-dione derivatives of Vinca alkaloids, useful as anti-tumor agents, synthesized from a C-3 carboxamide and a dialkyl carbonate.Type: GrantFiled: March 3, 1978Date of Patent: June 26, 1979Assignee: Eli Lilly and CompanyInventor: Jean C. Miller
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Patent number: 4154943Abstract: The invention relates to the preparation of vincadifformine.Tetrahydro-.beta.-carboline (II) is reacted with benzoyl chloride to provide 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido-[3,4b]-indole (III). Then compound (III) is reduced to give 2-benzyl-1,2,3,4-tetrahydro-9H-pyrido[3,4b]-indole (IV). Thereafter, compound (IV) is transformed by t-butyl hypochlorite into chloroindolenine derivative (V) which is immediately treated with thallium t-butyl methyl malonate to give t-butyl methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5,5-dicarboxylate (VI). Compound (VI) is then partly decarboxylated into methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5-carboxylate (VII). Compound (VII) is hydrogenated to give methyl 1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5-carboxylate (IX). In an alternative embodiment, compound (VI) can be hydrogenated to methyl t-butyl 1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5,5-dicarboxylate (VIII) which is then decarboxylated into compound (IX).Type: GrantFiled: December 29, 1977Date of Patent: May 15, 1979Assignee: University of VermontInventor: Martin E. Kuehne
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Patent number: 4152519Abstract: This invention relates to novel aspidospermidines being useful in synthesis and also exhibiting interesting physiological properties. A process for the preparation of the novel compounds is described and exemplified and examples of pharmaceutical compositions containing the novel compounds are given. Pharmacological test data are presented for a novel compound according to the invention.Type: GrantFiled: July 7, 1977Date of Patent: May 1, 1979Assignee: ParcorInventor: Alain Heymes
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Patent number: 4146643Abstract: Halo-, hydroxy-, alkyl- and alkoxy-vincamine derivatives are useful vigilance increasing agents.Type: GrantFiled: December 2, 1977Date of Patent: March 27, 1979Assignee: Sandoz Ltd.Inventor: Paul Pfaffli
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Patent number: 4145552Abstract: A process for preparing vincamine and related alkaloids, comprising reacting a compound of formula: ##STR1## (wherein R is H or methoxy and X and Y are hydrogen or together represent a double bond between the carbon atoms to which they are bonded) with a carbanion-forming agent in a reaction medium; then introducing oxygen into the reaction medium until saturation point, a reducing agent compatible with oxygen being added to the reaction medium before the medium ceases absorbing oxygen; acidifying the mixture and extracting therefrom a mixture of compounds ##STR2##Type: GrantFiled: July 5, 1977Date of Patent: March 20, 1979Assignee: ParcorInventor: Alain Heymes
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Patent number: 4140777Abstract: The invention relates to novel derivatives of vincamine and apovincamine having the formula ##STR1## WHICH ARE ENDOWED WITH ANALOGOUS PROPERTIES AS THE VINCAMINE AND APOVINCAMINE AS WELL AS WITH AN EXTENDED EFFECT. The invention relates also to the methods for the preparation of the above derivatives.Type: GrantFiled: May 31, 1977Date of Patent: February 20, 1979Assignee: Enrico Corvi MoraInventor: Davide Vegezzi