Abstract: Compounds of formula (I), wherein: R1 is —CN, —CH(CN)—R4, —CH═C(CN)—R4, —CH2—CH(CN)—R4, —C(═NOH)—NH2, —C(═NH)—NH2, —CH═C(NO2)—R4, —CH(CN)—R5, —CH(CH2NO2)—R5; 5-tetrazolyl, 2-(4,5-dihydrooxazolyl), 1,2,4-oxadiazolin-3-yl-5-one; R2 is hydrogen; R3 is hydrogen, OR6; R4 is hydrogen, C1-C6 linear or branched alkyl, CN, COOR7; R5 is hydrogen, OR8; R6 is hydrogen, C1-C6 linear or branched alkyl, (C6-C12) aryl (C1-C4) alkyl, (C1-C4) alkoxy (C1-C4) alkyl, (C1-C4) alkyl (C6-C12) aryl, (C6-C12) aryl (C2-C4) acyl, (C2-C4) acyl, amino (C1-C4) alkyl, amino (C2-C4) acyl, glycosyl; R7 is hydrogen, C1-C6 linear or branched alkyl, (C6-C12) aryl (C1-C4) alkyl, (C1-C4) alkoxy (C1-C4) alkyl, (C1-C4) alkyl (C6-C12) aryl; R8 has the same meanings of R6, independently of the latter. These compounds are active as topoisomerase I inhibitors and can be used as antitumor drugs.

Abstract: A process for preparing S type 2-substituted hydroxy-2-indolidinyl-butyric ester compound [II]: wherein R0 is residue of nitrogen-containing fused heterocyclic carboxylic acid having absolute configuration of “R”(in which the nitrogen atom is protected), R1 and R2 are lower alkyl group, and E is ester residue, which is useful as an intermediate for preparing camptothecin derivatives having antitumor activities, which comprises 2-ethylating 2-substituted hydroxy-2-indolidinylacetic ester compound [I]: wherein the symbols are as defined above.

Abstract: The present invention provides a short, convergent total synthesis of irinotecan and derivative compounds which comprises of a novel 4+1 radical annulation wherein the precursor is reacted with an aryl isonitrile having the formula wherein X is Br or I, and R4 is an alkyl group, an allyl group, a propargyl group or a benzyl group, and R16 is H, a C1-C6 alkoxy group, a group wherein p is an integer between 4 and 12, or a C1-C12 acyclic dialkylamino group. The present invention also provides novel chemical intermediates for such 4+1 radical annulations.

Abstract: Aromatic camptothecin ester compounds having the formula: are described as well as formulations containing the compounds. Methods of treating cancer and/or tumors are also disclosed.

Abstract: A novel phenanthridinium derivative represented by general formula (A): wherein R1 is a substituted or unsubstituted lower aliphatic hydrocarbon group; R is an aliphatic hydrocarbon chain having 2 to 6 carbon atoms which may optionally be substituted with a substituent selected from the group consisting of a lower alkyl group, a halogen and a hydroxy group; each of Y and Z independently represents a hydrogen, a hydroxy or a lower alkoxy group; or Y and Z are combined together to form methylenedioxy or a phenyl ring; and, X− is an acid residue or a hydrogen acid residue, exhibits an antitumor activity and has resistance to chemical reduction as well as biological metabolic reactions and is thus advantageous for use as a medicine.

Abstract: 20S-Camptothecin derivatives in which the 7-position bears as a substituent --CN, --CH(CN)R.sub.4, --CH.dbd.C(CN)R.sub.4, --C(.dbd.NOH)NH.sub.2, --C(.dbd.NH)NH.sub.2, --CH.dbd.C(NO.sub.2)R.sub.4, --CH(CN)R.sub.5, --CH(CH.sub.2 NO.sub.2)R.sub.5, tetrazol-5-yl, 4,5-dihydrooxazol-2-yl, or 1,2,4-oxadiazolin-3-yl-5-one. These compounds are active as topoisomerase I inhibitors, and can be used as antitumor drugs.

Abstract: The invention relates to novel racemic and optically active trans apovincaminic acid ester derivatives of formula (I), ##STR1## wherein R means hydrogen or a group (a), wherein Z stands for C.sub.1-4 alkyl, optionally substituted aryl, aralkyl, heteroaryl or 14-eburnameninyl group; and n is an integer of 2, 3 or 4, as well as therapeutically acceptable salts thereof. The invention further relates to pharmaceutical compositions containing these compounds as well as a process for the preparation of the above compounds and compositions, and in addition, to a method of treatment. The novel compounds of Formula (I) exhibit particularly antioxidant, antiischemic as well as antiamnesic effects and are useful for inhibiting lipid peroxidation and for protection from or treatment of ischemia and amnesia as well as for treating various degenerative neurological diseases, e.g. Alzheimer's disease.

Abstract: The present invention is directed compositions of the formula: ##STR1## wherein: D is a residue of biologically active moiety;X is an electron withdrawing group;Y and Y' are independently O or S;(n) is zero (0) or a positive integer, preferably from 1 to about 12;wherein: R.sub.1 and R.sub.2 are independently selected from the group consisting of H, C.sub.1-6 alkyls, aryls, substituted aryls, aralkyls, heteroalkyls, substituted heteroalkyls and substituted C.sub.1-6 alkyls;wherein: R.sub.3 is a substantially non-antigenic polymer, C.sub.1-12 straight or branched alkyl or substituted allyl, C.sub.5-8 cycloalkyl or substituted cycloalkyl, carboxyalkyl, carboalkoxy alkyl, dialkylaminoalkyl, phenylalkyl, phenylaryl or ##STR2## wherein: R.sub.4 and R.sub.5 are independently selected from the group consisting of H, C.sub.1-6 alkyls, aryls, substituted aryls, aralkyls, heteroalkyls, substituted heteroalkyls, and substituted C.sub.1-6 alkyls or jointly form a cyclic C.sub.5 -C.sub.7 ring.

Abstract: High molecular weight, water-soluble prodrugs of the formula: ##STR1## wherein: D is a biologically active moiety;M is X or Q;X is an electron withdrawing group;Q is a moiety containing a free electron pair positioned five or six atoms from Y';Y and Y' are oxygen or sulfur;R is a polyalkylene oxide; andZ is OH, C.sub.1-4 all moieties or ##STR2## are disclosed. In preferred embodiments, the prodrugs contain a polyethylene glycol having a molecular weight of at least about 20,000.

Abstract: This invention is concerned with 2-ureido-benzamide compounds of the formula (1) ##STR1## in which R.sup.1 is H, halogen atom, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy or (C.sub.1 -C.sub.4)dialkylamino and R.sup.2 is H, halogen atom, hydroxy, nitro, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, (C.sub.3 -C.sub.6) cycloalkylmethoxy, (C.sub.1 -C.sub.4) alkylthio, (C.sub.1 -C.sub.4) alkylsulfinyl, (C.sub.1 -C.sub.4)alkylsulfonyl or ##STR2## wherein j is an integer of from 0 to 2 and R.sup.3 and R.sup.4 are each independently H, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkanoyl, (C.sub.1 -C.sub.4)alkylsulfonyl or (C.sub.1 -C.sub.4)alkylcarbamoyl, NR.sup.3 R.sup.4 can to form a pyrrolidine, piperidine, morpholine, imidazole or pyrazole ring;X is a (C.sub.3 -C.sub.15)alkyl, (C.sub.3 -C.sub.6) cycloalkyl, (C.sub.3 -C.sub.6) cycloalkylmethyl, .omega.-(C.sub.1 -C.sub.4) alkoxy-(C.sub.1 -C.sub.4) alkyl group or ##STR3## wherein k is an integer of from 1 to 4 and R.sup.5 and R.sup.

Abstract: The present invention is directed compositions of the formula: ##STR1## wherein: D is a biologically active moiety;X is an electron withdrawing group;Y and Y' are independently O or S;R.sub.1 is selected from the group consisting of H, C.sub.1-6 alkyls, aryls, substituted aryls, aralkyls, heteroalkyls, substituted heteroalkyls and substituted C.sub.1-6 alkyls;(n) is an integer from 1 to about 12; andR.sub.2 is a polyalkylene oxide.In preferred embodiments, the prodrugs contain a polyethylene glycol having a molecular weight of at least about 20,000.

Abstract: A compound selected from those of general formula (I): ##STR1## wherein A represents a bivalent radical ##STR2## and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.6, R.sub.7, R.sub.8, R.sub.9 and Z are as defined in the description,the isomers and pharmaceutically-acceptable acid or base addition salts thereof, and medicinal products containing the same which are useful in the treatment of depression and anxiety.

Abstract: Water-soluble prodrugs of the formula: ##STR1## wherein: D is a biologically active nucleophile;M is X or Q;x is an electron withdrawing group;Q is a moiety containing a free electron pair positioned five or six atoms from Y';Y and Y' are oxygen or sulfur;R is a polyalkylene oxide; andZ is OH, C.sub.1-4 alkyl moieties or ##STR2## are disclosed.

Abstract: A compound selected from those of general formula (I): ##STR1## wherein A represents a bivalent radical selected from ##STR2## and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9 and Z are as defined in the description,the isomers and pharmaceutically-acceptable acid or base addition salts thereof, and medicinal products containing the same which are useful in the treatment of depression and anxiety.

Abstract: Derivatized drugs are prepared with a linker consisting of a malonate, wherein the drug is linked through a methylene to the 2-position carbon of the malonate.

Abstract: A compound in all racemic or optionally active forms selected from the group consisting of a compound of the formula ##STR1## where the substituents are defined as in the specification and their non-toxic, pharmaceutically acceptable acid addition salts having anti-anoxic activity and a novel process and intermediates for their preparation.

Abstract: A compound and all possible racemic or optically active isomer forms, selected from the group consisting of compound of the formula ##STR1## wherein the substituents are defined as set forth in the application as filed. Useful for treating cerebral insufficiencies of anoxic or ischemic origin.

Abstract: The invention is a de novo synthesis of the norcatharanthine moiety of navelbine. The synthesis includes condensing a Grignard reagent prepared from an amine-protected R(+)-piperidinyl methanol with an N-protected 2-methoxyoxalyl indole. The indole N-protecting group is removed to provide a 2-methoxyindole hydroxy ester which is coupled to vindoline. After removal of the amineprotecting group from the piperidinyl group, ring closure to the indole moiety provides dihydrodesethyl navelbine. Other derivatives and analogs of navelbine with potential clinical applications in cancer chemotherapy may be readily synthesized. The synthesis opens a route to a wide variety of navelbine modifications, including modifications at or near the tryptamine bridge.

Abstract: The invention relates to novel 15-nitro-2.beta.,3.beta.-dihydro- and 15-nitro-2.beta.,3.beta.,6,7-tetrahydrotabersonine derivatives of the formula (I), ##STR1## wherein R.sup.1 stands for hydrogen;R.sup.2 stands for hydrogen or a C.sub.1-6 alkyl group; and the symbolrepresents a single or double bond as well as their salts.The invention further relates to pharmaceutical compositions containing the above compounds as well as a process for the preparation of the above compounds of formula (I) and of the pharmaceutical compositions.The compounds of formula (I) exert a reducing or inhibitory effect on cerebral edema and show antihypoxic properties. Thus, they are useful for the prevention or treatment of brain injuries of various origin induced by hypoxia of the brain.

Abstract: New intermediate compounds are disclosed of the formula I, ##STR1## wherein R.sub.1 and R.sub.2 are independently alkyl having 1 to 4 carbon atoms,or acid-addition salts thereof of formula Ib, ##STR2## wherein X represents an acid residue, and a process for the preparation of the intermediate compounds.

Abstract: The invention concerns compounds of formula (I); ##STR1## in which R.sub.1, R.sub.2 and R.sub.3, identical or different, stand for hydrogen, halogen, alkyl or alkoxy (C.sub.1-5), hydroxy, trifluoromethyl, nitro, amino, alkylamino, dialkylamino, acylamino, R.sub.1, R.sub.2 and R.sub.3 being unable to stand for hydrogen simultaneously and in which (a) stands for (b), (c), or (d), all possible isomeric forms of said products of formula (I) being racemic or optically active, as well as their additional salts with acids, their preparation and the new intermediate products obtained, their application as drugs in particular nootropes, antidepressants, neuronal protectors, anti-anoxics, anti-ischemics, and the compositions containing them.

Abstract: A compound selected from the group consisting of a compound of the formula (I): ##STR1## in which R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, an alkyl of 1 to 5 carbon atoms, --(CH.sub.2).sub.n --OH in which n is between 2 and 5, an aryl or arylalkyl of 7 to 12 carbon atoms, these two radicals being optionally substituted, ##STR2## in which R.sub.3 is an alkyl of 7 to 12 carbon atoms, these two radicals being optionally substituted, with the proviso that R.sub.1 and R.sub.2 are not both aryl simultaneously, or R.sub.1 and R.sub.2 form, together with the nitrogen atom to which they are linked, a saturated or unsaturated heterocyclic which can contain a second heteroatom chosen from oxygen, sulphur and nitrogen optionally substituted by an alkyl of 1 to 5 carbon atoms, aryl, arylalkyl of 7 to 12 carbon atoms, these radicals being optionally substituted, R.sub.4 and R.sub.

Abstract: The present invention relates to the synthesis of dimer alkaloid compounds, particularly those of the Catharantus (Vinca) family, from an indole unit, such as cantharanthine, and a dihydroindole unit, such as vindoline. A multi-step process is disclosed including the steps of (1) of 1,4-reduction of a first dimeric iminium intermediate to an enamine compound by reaction with a 1,4-dihydropyridine compound; (2) oxidative transformation of the resulting enamine to a second iminium intermediate under controlled aeration; (3) reduction of the second iminium intermediate to form the target dimer alkaloid compounds. The entire process can be conducted in a one-pot operation to obtain the target compounds without isolation of the intermediates.

Abstract: This invention concerns a method for the production of dimeric alkaloids, characterized by reacting of catharanthine with vindoline in the presence of Fe.sup.3+ and (1) removing or inactivating the Fe.sup.3+ and allowing the reaction product to react with a reducing agent or (2) allowing presence of oxygen and a dicarboxylic acid or a derivative thereof in the reaction system and allowing the reaction product to react with a hydride source.In accordance with this invention, such dimeric alkaloid as vinblastine, leurosidin, and 3',4'-anhydrovinblastine which are useful as antineoplastic drugs can be produced in high yields.

Abstract: A compound selected from the group consisting of optically active isomers of a racemic compound of the formula ##STR1## wherein the 3-hydrogen and 16-hydrogen are trans and ##STR2## is selected from the group consisting of ##STR3## with the --OH being .alpha. or .beta. and their non-toxic, pharmaceutically acceptable acid addition salts having antidepressant activity and an affinity for alpha.sub.

Abstract: An apovincaminic acid derivative represented by the formula ##STR1## wherein n is an integer of from 2 to 11, and a pharmaceutically acceptable salt thereof are disclosed. These compounds are useful for therapy of cerebrovascular injuries, peripheral vessel injuries, angina pectoris, hypertension and senile dementia.

Abstract: A novel hexa-cyclic compound, a derivative of camptothecin, of the general formula: ##STR1## The compound is prepared from an aminoketone compound and a pyranoindolizine compound through Friedlaender reaction. It has an excellent antitumor activity and a high degree of safety, and can be applied as an antitumor medicine for curing tumors of various kinds.

Abstract: A new process for the stereospecific synthesis of alkaloids of the vinblastine and vincristine type including the synthesis of vinblastine and vincristine as well novel alkaloids which are active as anti-tumor agents.

Abstract: Vincaminic acid derivatives represented by the formula ##STR1## wherein R.sup.1 is a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or an alkoxyalkyl group having 2 to 6 carbon atoms, R.sup.2 is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkoxycarbonylallyl group having 3 to 8 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, a phenyl group, a phenyl group substituted by alkoxy groups each having 1 or 2 carbon atoms or a thienyl group, A is a hydroxy group, B is a hydrogen atom, or A and B together form a valence bond, and the acid addition salts thereof are disclosed. These compound are useful as thereapeutic effect on cerebovascular injuries.

Abstract: A process for preparing the ethyl ester of apovincaminic acid by reacting the apovincaminic acid with ethyl alcohol and in the presence of aminopyridine and trinitrobenzene derivatives. The product is useful as a cerebral vasodilator.

Abstract: A new process for the stereospecific synthesis of alkaloids of the vinblastine and vincristine type including the synthesis of vinblastine and vincristine as well novel alkaloids which are active as anti-tumor agents.

Abstract: The invention relates to the preparation of cis and trans stereoisomers of racemic and optically active eburnamenine derivatives of the general formula (Ia) ##STR1## or (Ib), ##STR2## wherein R.sub.1 stands for a C.sub.1-4 alkyl group; andR stands for hydrogen, a C.sub.1-6 alkyl group, a C.sub.2-6 alkenyl group, an acyl or substituted acyl group,as well as their acid addition salts, of which the trans compounds are novel.The invention also relates to the compounds of the general formula (IIIa) ##STR3## and (IIIb), ##STR4## wherein R.sub.1 and R' represent a C.sub.1-4 alkyl group. The compounds of the general formulae (Ia) and (Ib) possess a vasodilatory effect which is substantially higher than that of pentoxifyllin, a known peripheral vasodilator.

Abstract: Pharmaceutical compositions for combatting cancer comprising a compound of formula (I) ##STR1## (wherein R.sup.1 represents a hydrogen atom or a C.sub.1-4 alkyl, C.sub.2-4 alkenyl or C.sub.2-4 alkynyl group;R.sup.2 represents a hydrogen atom or a hydroxyl, C.sub.1-4 alkoxy or C.sub.2-4 alkanoyloxy group;R.sup.3 represents a hydrogen atom, or (when R.sup.2 is other than a hydrogen atom) optionally a hydroxyl, C.sub.1-4 alkoxy or C.sub.2-4 alkanoyloxy group, or R.sup.2 and R.sup.3 together represent a methylenedioxy group;R.sup.4 represents a hydrogen or halogen atom or a C.sub.1-3 alkyl group or a phenyl group optionally substituted by a halogen atom or a hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or C.sub.1-4 alkanoyloxy group; and the ring A represents a group of formula ##STR2## where R.sup.5 and R.sup.6 each represent a hydrogen atom or a hydroxyl, C.sub.1-4 alkoxy or C.sub.1-4 alkanoyloxy group,R.sup.7 and R.sup.8 each represents a hydrogen atom or a methyl group, and one of X, X.sup.1, X.sup.2 and X.sup.

Abstract: The invention relates to a new process for preparing novel racemic and optically active 9- or 11-nitroapovincaminic acid derivatives of the general formula (I) ##STR1## wherein R stands for a --CO--X group, wherein X means a halogen atom; orfor a --CO--OR.sup.1 group, wherein R.sup.1 means an optionally mono- or polysubstituted C.sub.1-10 aliphatic group, a C.sub.3-8 alicyclic group or an aromatic C.sub.6-14 hydrocarbyl group; orfor a --CO--NR.sup.2 R.sup.3 group, wherein R.sup.2 and R.sup.3 are the same or different and stand for a hydrogen atom or a C.sub.1-8 alkyl group optionally forming a saturated heterocycle together with the adjacent nitrogen atom and optionally with one or more further nitrogen atoms or other heteroatoms, and R.sup.3 may also represent an amino group when R.sup.2 stands for a hydrogen atom; orfor a cyano group,as well as their salts and pharmaceutical preparations containing these compounds.

Abstract: The invention relates to a new process for the preparation of 17,18-dehydro-apovincaminol-trimethoxy-benzoate of the formula (I) ##STR1## and acid addition salts thereof. According to the invention compound of the formula (I) is prepared starting from 17,18-dehydrovincamine of the formula (IIa) ##STR2## and/or 17,18-dehydro-epivincamine of formula (IIb) ##STR3## by reducing with a complex metal hydride, acylating the new hydroxy-vincaminol derivative obtained selectively with 3,4,5-trimethoxy-benzoic acid or a derivative thereof capable of acylation, optionally in the presence of a catalyst and/or an acid binding agent, and treating the corresponding acylated hydroxylderivative obtained with formic acid, in the presence of an acid chloride, and, if desired, converting the compound of formula (I) obtained into an acid addition salt thereof.

Abstract: A (+) citrate salt of vinpocetine, and a procedure for preparing the salt, is disclosed. The salt is useful as a medicinal agent in cerebral-vascular disorders and in neurological treatments relating to cerebral oxygenation, especially in elderly persons.

Abstract: The invention relates to new eburnane derivatives of the formula (I) ##STR1## wherein R.sup.1 is alkyl having from 1 to 6 carbon atoms, and acid addition salts thereof.The invention further relates to a process for the preparation of these compounds and pharmaceutical compositions containing them.Compounds of formula (I) show remarkable CNS-activity and are useful intermediates in the preparation of other, pharmaceutically active compounds.

Abstract: There is disclosed novel eburnamonine oxime, its derivatives and salts, process for the manufacture thereof and pharmaceutical agents containing the same. The compounds are represented by the following formula. ##STR1## wherein R is hydrogen, alkyl, alkoxyalkyl, or oxisilanylalkyl group or a group of ##STR2## R.sup.1 and R.sup.2 are same or different and respectively hydrogen, alkyl having 1 to 4 carbon atoms, aryl or aralkyl group, or R.sup.1 represents together with R.sup.2 and the neighboring nitrogen atom a non-substituted or substituted heterocyclic ring, and n is an integer of 2 or 3.

Abstract: The invention relates to new apovincaminol derivatives of the formula /I/ ##STR1## wherein R.sub.1 is hydrogen, nitro or halogen,R.sub.2 is a substituted or unsubstituted alkyl or phenyl group,R.sub.3 and R.sub.4 together form a valency bond or each independently represents hydrogen, hydroxyl or an --OR.sub.5 group, in whichR.sub.5 is substituted or unsubstituted alkanoyl or benzoyl group,with the proviso that if R.sub.2 stands for a 3,4,5-trimethoxyphenyl group and R.sub.1 is hydrogen, R.sub.3 and R.sub.4 together do not form a valency bond, or if R.sub.2 is a 3,4,5-trimethoxyphenyl group and R.sub.3 and R.sub.4 both are hydrogen, R.sub.1 is other than hydrogen, nitro or bromine, and acid addition salts thereof.The compounds may be used in the therapy of various skin diseases accompanied by a pathological cell proliferation, preferably psoriasis.

Abstract: A process is disclosed for the preparation of dimeric alkaloids of formula (II) ##STR1## wherein R stands for methyl or formyl, as well as acid addition salts thereof which comprises oxidizing the vinblastine of formula (III) ##STR2## with chromium (VI) oxide or bichromate or chromic acid alcohol ester in an inert solvent, converting the compound of formula (II), wherein R stands for methyl, so obtained to the acid addition salt and optionally further oxidizing the acid addition salt obtained with an oxidizing agent as defined above and optionally converting the compound of formula (II), wherein R stands for formyl, so obtained to the acid addition salt.

Abstract: The invention relates to new racemic and optically active apovincaminic acid derivatives of the general formula (I) ##STR1## wherein A is hydroxyl, halogen or a group --O--(CH.sub.2).sub.n --OR.sup.1 or --OMe, in whichR.sup.1 is alkyl having from one to 6 carbon atoms,n is an integer between 2 and 6,Me is an alkali metal,R.sup.2 stands for an alkyl group having from one to 6 carbon atoms, which may be identical with or different from R.sup.1,and the hydrogen in the 3-position and the R.sup.2 group have an .alpha.,.alpha.- and/or .beta.,.beta.- or .alpha.,.beta.- and/or .beta.,.alpha.-configuration, and pharmaceutically acceptable acid addition salts thereof, which are pharmaceutically active, e.g. show antihypoxial activity or are potent peripheral vasodilators. Their preparation and pharmaceutical composition containing them are also within the scope of the invention.

Abstract: The invention relates to new indolo[2,3-g]cyclopent[a]indolizine derivatives of the formulae (II) ##STR1## and/or (III) ##STR2## wherein W is alkoxycarbonyl having from one to four carbon atoms in the alkoxy moiety or cyano,R.sub.1 is hydrogen or alkyl having from one to four carbon atoms,G is a >CH.sub.2 or >C.dbd.O group, andX and Y each stands for hydrogen or together represent a C--C bond.According to another aspect of the invention there is provided a process for the preparation of the above compounds, which are pharmaceutically active, in particular, possess valuable gastric acid secretion inhibiting activity. Pharmaceutical compositions containing compounds of the formulae (II) and/or (III) are also within the scope of the invention.

Abstract: The invention relates to racemic or optically active eburnane derivatives of the formula (I), ##STR1## wherein R represents an alkyl group having 1 to 6 carbon atoms,A stands for hydroxyl andY is hydrogen, orA and Y together form an oxo group,and the configuration of the hydrogen in the 3-position and of R is .alpha.,.alpha. and/or .beta.,.beta. or .alpha.,.beta. and/or .beta.,.alpha.,and acid addition salts thereof.The new compounds possess valuable pharmaceutical properties, thus their certain representatives show antiallergic activity, while others are potent antidepressive, gastric secretion inhibiting and anticonvulsive agents. The compounds of the formula (I) and pharmaceutically acceptable acid addition salts thereof can therefore be employed as active ingredients of pharmaceutical compositions, which are also within the scope of the invention.

Abstract: The invention relates to optically active or racemic eburnane-oxime ethers of the formulae (Ia) and/or ##STR1## wherein R represents an alkyl group having 1 or 2 carbon atoms,R.sup.2 represents an alkyl group having 1 to 6 carbon atoms,and the configuration of the hydrogen in the 3-position and the R.sup.2 group is .alpha.,.alpha. and/or .beta.,.beta. or .alpha.,.beta. and/or .beta.,.alpha. and acid addition salts thereof.The new compounds show valuable pharmaceutical activities, thus are potent CNS-tranquillants, smooth muscle relaxants, sedatives and hypnotic agents, and can therefore be employed as active ingredients of pharmaceutical compositions, which are also within the scope of the present invention.

Abstract: Novel 20,21-dinoreburnamenines of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and .dbd.CH.sub.2, the wavy line connecting to the E ring being a single bond when R is hydrogen or alkyl of 1 to 4 carbon atoms or a double bond when R is .dbd.CH.sub.2 and the dotted line being possibly an endo carbon-carbon bond when R is hydrogen or alkyl of 1 to 4 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts in all their possible isomers forms, racemic mixtures and optical isomers having oxygenating and cerebral vasoregulating activity of great value and a novel process and intermediates for their preparation.

Abstract: 13a-ethyl-2,3,5,6,13a,13b-hexahydro-1H-indolo (3,2,1-de)pyrido (3,2,1-ij) (1,5) naphthiridin-12-phthalidile carboxylate, having the formula given below, and a procedure for its preparation, are described. ##STR1## The compound lends itself to the prevention and treatment of cerebrovascular affections and organic and functional syndromes caused by a deterioration of cerebral circulation.

Abstract: The invention relates to a new process for the preparation of apovincaminic acid esters. More particularly, the invention concerns a process for preparing racemic and optionally active vincaminic acid esters of the formula (I) ##STR1## in which R.sup.1 and R.sup.2 independently stand for alkyl having from one to 6 carbon atoms, and 14-epimers thereof.According to the invention an octahydroindolo[2,3-a]quinolizine-oxime ester of the formula (II) ##STR2## in which R.sup.1 and R.sup.2 have the same meaning as defined above, is reacted with an aqueous solution of sulfurous acid or a salt thereof at a temperature of 80.degree. to 110.degree. C. and the 14-epimeric mixture obtained is epimerized or separated in a known manner and if desired, the racemic vincaminic acid esters are resolved.

Abstract: The invention relates to a new process for the preparation of eburnamonine derivatives of the general Formula I ##STR1## (wherein R.sup.1 is an alkyl group having 1-6 carbon atoms) and optical and geometrical isomers thereof which comprises reacting a hydroxyimino-octahydro-indolo[2,3-a]quinolizine derivative of the general Formula II ##STR2## (wherein R.sup.1 is as stated above and R.sup.2 stands for an alkyl group having 1-6 carbon atoms being identical with or different from R.sup.1, or a hydrogen atom) or an acid addition salt thereof in an organic protic solvent or solvent mixture with an inorganic base, optionally under the addition of water or an aqueous mineral acid, at a temperature between 60.degree. C. and 200.degree. C.The compounds of the present invention are known drugs having blood pressure decreasing and cerebral vasodilatatory effect.

Abstract: 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.

Abstract: The present invention relates to the synthesis of dimer alkaloid compounds, particularly those of the Catharantus (Vinca) family, from an indole unit, such as cantharanthine, and a dihydroindole unit, such as vindoline. A multi-step process is disclosed including the steps of (1) of 1,4-reduction of a first dimeric iminium intermediate to an enamine compound by reaction with a 1,4-dihydropyridine compound; (2) oxidative transformation of the resulting enamine to a second iminium intermediate under controlled aeration; (3) reduction of the second iminium intermediate to form the target dimer alkaloid compounds. The entire process can be conducted in a one-pot operation to obtain the target compounds without isolation of the intermediates.