Abstract: The 17?-cyano-19-nor-androst-4-ene derivatives of the present invention possess gestagenic activity.

Abstract: A process for manufacturing a 5-formyl-pyridine-2,3-dicarboxylic acid ester (I) wherein Z is hydrogen or halogen; Z1 is hydrogen, halogen, cyano or nitro and R1, R2 are independently C1-C10-alkyl, comprising the steps of (i) reacting a compound of formula (II), wherein the symbols are as in formula (I), with a nitrosation agent (III) R3—O—N?O (III) wherein R3 is C1-C8-alkyl, in the presence of an alkali metal or alkaline earth metal alcoholates or carbonates in a polar aprotic solvent at a temperature of from ?45 to 40° C., to obtain an oxime compound (IV) where Z, Z1, R1 and R2 are as in formula (I), and (ii) reacting oxime compound (IV) with an aliphatic C1-C10-aldehyde in the presence of a Lewis acid at a temperature in the range of from 0 to 100° C. The compounds of formula (I) are useful intermediates in the synthesis of herbicidal imidazolinones, like imazamox.

Abstract: A process for manufacturing 5-chloromethyl-2,3-pyridine dicarboxylic acid anhydrides (I) wherein Z is hydrogen or halogen; Z1 is hydrogen, halogen, cyano or nitro; comprising the steps of (i) reacting a compound of formula (II), wherein the symbols have the meaning given in formula (I), with a chlorinating agent, optionally in the presence of a radical initiator in a solvent selected from halogenated hydrocarbons, and (ii) crystallizing the compound (I) formed in step (i) from a solvent selected from chlorobenzene, 1,2-dichlorobenzene, 1,3-dichlorobenzene, 1,4-dichlorobenzene, dichloroethane, trichloromethane, dichloromethane, toluene, xylenes, ethyl acetate, methyl tert.-butyl ether, and mixtures thereof. Compounds (I) are useful intermediates in the synthesis of herbicidal imidazolinones.

Abstract: A process for manufacturing 5,6-disubstituted-3-pyridylmethyl ammonium bromides (I), wherein Q is a tertiary aliphatic or cyclic, saturated, partially unsaturated or aromatic amine; Z is hydrogen or halogen; Z1 is hydrogen, halogen, cyano or nitro; Y and Y1 are each independently OR1, NR1R2, or when taken together YY1 is —O—, —S— or NR3—; R1 and R2 are each independently hydrogen, C1-C4 alkyl optionally substituted with C1-C4 alkoxy or phenyl optionally substituted with one to three C1-C4 alkyl groups, C1-C4 alkoxy groups or halogen atoms, or phenyl optionally substituted with one to three C1-C4 alkyl groups, C1-C4 alkoxy groups or halogen atoms; R3 is hydrogen or C1-C4 alkyl; comprises the steps of (i) reacting a compound of formula (II), wherein the symbols have the meaning given in formula (I), with bromine in the presence of a radical initiator in a solvent mixture comprising an aqueous phase and an organic phase, where the organic phase comprises a solvent selected from 1,2-dichloroethane,

Abstract: 2-[(1-cyanopropyl)carbamoyl]-5-chloromethyl nicotinic acids of formula (I) where Z is hydrogen or halogen; Z1 is hydrogen, halogen, cyano or nitro; R1 is C1-C4 alkyl; R2 is C1-C4 alkyl, C3-C6 cycloalkyl or R1 and R2, when taken together with the atom to which they are attached, represent a C3-C6 cycloalkyl group optionally substituted with methyl, and R3 is hydrogen or a cation preferably selected from the group consisting of alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium and organic ammonium; are useful intermediates for the synthesis of herbicidal imidazolinones.

Abstract: The invention relates to 17-hydroxy-19-nor-21-carboxylic acid-steroid ?-lactone derivatives with the chemical formula I, where R4, R6a, R6b, R7, R15, R16a, R16b, R18 and Z have the meanings stated in claim 1, and their solvates, hydrates, stereoisomers and salts. The invention further relates to the use of these derivatives for the production of a medicinal product for oral contraception and for the treatment of pre-, peri- and postmenopausal complaints and medicinal products that contain said derivatives. The derivatives according to the invention have a progestational and in preferred cases additionally an antimineralocorticoid and neutral to slightly androgenic action.

Abstract: The invention relates to 15,16-methylene-17-hydroxy-19-nor-21-carboxylic acid-steroid ?-lactone derivatives with the general chemical formula I, and R4, R6a, R6b, R7 and Z have the meanings stated in claim 1, and their solvates, hydrates, stereoisomers and salts. The invention further relates to the use of these derivatives for the production of a medicinal product for oral contraception and for the treatment of pre-, peri- and postmenopausal complaints and medicinal products that contain said derivatives. The derivatives according to the invention have a progestational and in preferred cases additionally an antimineralocorticoid and neutral to slightly androgenic action.

Abstract: The invention relates to 15,16-methylene-17-(1?-propenyl)-17-3?-oxidoestra-4-en-3-one derivatives with the general chemical formula I, where the Z, R4, R6a, R6b, R7 and R18 have the meanings stated in claim 1, and solvates, hydrates and salts thereof, including all crystal modifications and all stereoisomers of these compounds. The invention also relates to the use of these derivatives for the production of a drug for oral contraception and for the treatment of pre-, peri- and postmenopausal problems and drugs which contain such derivatives, in particular use in the aforesaid indications. The derivatives according to the invention have a progestational and in preferable cases also an antimineralcorticoid and neutral to slight androgenic activity.

Abstract: The invention relates to 17-(1?-propenyl)-17-3?-oxidoestra-4-en-3-one derivatives with the general chemical formula I, where the residues Z, R4, R6a, R6b, R7, R15, R16a, R16b and R18 have the meanings stated in Claim 1, and their solvates, hydrates and salts, including all stereoisomers of these compounds. The invention further relates to the use of these derivatives for the production of a medicinal product for oral contraception and for the treatment of pre-, peri- and postmenopausal complaints and medicinal products that contain said derivatives, and in particular application in the aforementioned indications. The derivatives according to the invention have a progestational and in preferred cases additionally an antimineralocorticoid and neutral to slightly androgenic action.

Abstract: The 15?,16?-methylene-17-hydroxy-19-nor-17-pregna-4-en-3-one-21-carboxylic acid ?-lactone derivatives of the present invention possess progestational efficacy. They have the general chemical formula I, in which Z is selected from the group comprising an oxygen atom, two hydrogen atoms, NOR and NNHSO2R, where R is hydrogen, C1-C10-alkyl, aryl or C7-C20-aralkyl, R4 is hydrogen or halogen, and moreover either: R6a, R6b together form methylene or 1,2-ethanediyl or R6a is hydrogen and R6b is selected from the group comprising hydrogen, C1-C10-alkyl, C2-C10-alkenyl or C2-C10-alkynyl, and R7 is selected from the group comprising hydrogen, C1-C10-alkyl, C3-C6-cycloalkyl, C2-C10-alkenyl or C2-C10-alkynyl, or: R6a is hydrogen and R6b and R7, together, denote a bond, an oxygen or form methylene, R18 represents hydrogen or C1-C3-alkyl and in addition include their solvates, hydrates, stereoisomers and salts.

Abstract: The present invention describes the novel 18-methyl-19-norandrost-4-ene 17,17-spiro ethers of the general formula I in which Z is an oxygen atom, two hydrogen atoms, a group ?NOR or ?NNHSO2R, where R is a hydrogen atom or a straight- or branched-chain alkyl group having 1 to 4 or 3 to 4 carbon atoms, R4 is a hydrogen atom, a halogen atom or a trifluoromethyl group, and R6 and/or R7 may have ? or ? configuration, and R6 and R7 are independently of one another a hydrogen atom or a straight- or branched-chain alkyl group having 1 to 4 or 3 to 4 carbon atoms or a straight- or branched-chain alkenyl group having 2 to 4 or 3 to 4 carbon atoms or a saturated cycloalkyl group having 3 to 5 carbon atoms or together are a methylene group or a double bond. The novel compounds have progestational and antimineralocorticoid activity.

Abstract: The 17?-cyano-19-androst-4-ene derivatives of the present invention possess gestagenic activity.

Abstract: The 17?-cyano-19-nor-androst-4-ene derivatives of the present invention possess gestagenic activity.

Abstract: The present invention describes the novel 18-methyl-19-norandrost-4-ene 17,17-spiro ethers of the general formula I in which Z is an oxygen atom, two hydrogen atoms, a group ?NOR or ?NNHSO2R, where R is a hydrogen atom or a straight- or branched-chain alkyl group having 1 to 4 or 3 to 4 carbon atoms, R4 is a hydrogen atom, a halogen atom or a trifluoromethyl group, and R6 and/or R7 may have a or a configuration, and R6 and R7 are independently of one another a hydrogen atom or a straight- or branched-chain alkyl group having 1 to 4 or 3 to 4 carbon atoms or a straight- or branched-chain alkenyl group having 2 to 4 or 3 to 4 carbon atoms or a saturated cycloalkyl group having 3 to 5 carbon atoms or together are a methylene group or a double bond. The novel compounds have progestational and antimineralocorticoid activity.

Abstract: The invention relates to the (stereoselective) hydrogenation of carbon-carbon double bonds in compounds having at least one such bond, e.g., isoprenoids, non-cyclic sesquiterpenes, tocomonoenols, tocodienols, tocotrienols or derivatives thereof, as well as to the (stereoselective) hydrogenation of parts/extracts of plant oils containing such tocotrienols or derivatives thereof, in the presence of a chiral Ir complex as the catalyst, whereby preferably one stereoisomer is manufactured in an excess.

Abstract: Compounds of formulae I and Ia, wherein X1 is secondary phosphino; R3 is hydrogen, a hydrocarbon radical having from 1 to 20 carbon atoms, a heterohydrocarbon radical, bonded via a carbon atom, having from 2 to 20 atoms and at least one hetero atom selected from the group O, S and NR, or ferrocenyl; R is H or C1-C4alkyl; each R4 individually or both R4 together are a hydrocarbon radical having from 1 to 20 carbon atoms; and R01 and R02 are each independently of the other a hydrogen atom or a hydrocarbon radical having from 1 to 20 carbon atoms, are chiral ligands for metal complexes with metals of sub-groups I and VIII, which are catalysts for asymmetric addition reactions, for example of hydrogen, to prochiral unsaturated organic compounds.

Abstract: Compounds of formulae I and Ia, wherein X1 is secondary phosphino; R3 is hydrogen, a hydrocarbon radical having from 1 to 20 carbon atoms, a heterohydrocarbon radical, bonded via a carbon atom, having from 2 to 20 atoms and at least one hetero atom selected from the group O, S and NR, or ferrocenyl; R is H or C1-C4alkyl; each R4 individually or both R4 together are a hydrocarbon radical having from 1 to 20 carbon atoms; and R01 and R02 are each independently of the other a hydrogen atom or a hydrocarbon radical having from 1 to 20 carbon atoms, are chiral ligands for metal complexes with metals of sub-groups I and VII, which are catalysts for asymmetric addition reactions, for example of hydrogen, to prochiral unsaturated organic compounds.

Abstract: Compounds of formulae I and Ia, 1

Abstract: Compounds of formulae I and Ia, 1