公开(公告)号：SE348457B

公开(公告)日：1972-09-04

申请号：SE754266

申请日：1966-06-02

Applicant: HOECHST AG

Inventor： EHRHART G ,  LINDNER E ,  HAERTFELDER G ,  OTT H

IPC: C07C217/62 ,  C07D213/38 ,  C07C91/16 ,  C07D31/28

Abstract: Compounds of the general Formula (I) (wherein R1 represents a phenyl, methoxyphenyl or 2-pyridyl group, R2 represents a hydrogen atom or a methyl group and R3 and R4 each represent a C1- 4 alkyl group) and their acid addition salts are prepared by standard methods, e.g. reducing a compound of the Formula (II) (wherein R represents a hydrogen atom) or a salt thereof, or condensing a compound of the Formula (III) with a compound of the Formula (IV) (wherein X represents and reducing the product, optionally followed in either case by salt formation. The preparation of starting materials of Formulae (II) and (IV) is described. The compounds of the invention are useful in the treatment of hypertonia, and may be administered in the form of pharmaceutical preparations containing them in association with a carrier.

公开(公告)号：FI44617B

公开(公告)日：1971-08-31

申请号：FI140566

申请日：1966-05-27

Applicant: HOECHST AG

Inventor： EHRHART G ,  LINDNER E ,  OTT H

IPC: A61K31/195 ,  C07C101/18

Abstract: The invention comprises compounds of formula wherein R represents an alkyl radical containing from 1 to 4 carbon atoms, and R1 and R2, which may be the same or different, each represent hydrogen, an alkyl radical containing from 1 to 4 carbon atoms or halogen, and salts thereof. The compounds may be made by (a) reacting with in which R1 represents a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms and reducing, simultaneously or subsequently, the reaction product, or (b) reacting in the presence of aldehyde of formula (C6H2)2CH-CH2-CHO or (C6H5)2C=CH-CHO and reducing, simultaneously or subsequently, the reaction product and hydrogenating any aliphatic C-C double linkage present, or (c) reacting (C6H5)2CH-CH2-CH2-Hal with wherein Hal represents a halogen atom and R3 represents a hydrogen atom or the benzyl radical, if desired or required in the presence of agents splitting off hydrogen halide, or (d) reacting diphenyl methane or diphenyl acetonitrile with a compound of formula in the presence of agents splitting off hydrogen halide and replacing the nitrile group which may be present in the reaction products by a hydrogen atom by heating with sodium amide in an inert organic solvent, and removing by catalytic hydrogenation the N-benzyl group which may be present, and if compounds of the general Formulae III, IV, VIII, and IX are used, in which R1 represents a hydrogen atom, esterifying the free carboxyl group by reaction with an alcohol containing from 1 to 4 carbon atoms, and, if desired, converting the basic compounds thus obtained into their salts by means of mineral or organic acids. Pharmaceutical compositions, for use in curing cardiac and circulatory disorders, comprise the above compounds, or salts, in admixture with a pharmaceutically suitable carrier. The compositions may be made up in the usual dosage unit forms for oral or parenteral administration, such as tablets, dragees, capsules, ampoules, solutions, emulsions or suspensions.

公开(公告)号：SE321217B

公开(公告)日：1970-03-02

申请号：SE754466

申请日：1966-06-02

Applicant: HOECHST AG

Inventor： EHRHART G ,  LINDNER E ,  OTT H

IPC: A61K31/135 ,  C07C87/02

Abstract: Novel 1-phenyl-3-aminopropane derivatives of the formula wherein R is hydrogen or methyl and each of R1 and R2 is hydrogen or C1- 4 alkyl, and their physiologically tolerable, acid-addition salts, are prepared by (a) reacting 1-phenyl-1-cyclohexen-(11)-yl-3-aminopropane with a ketone of the formula and simultaneously or subsequently reducing the C-N double bond in the condensation product obtained, or (b) reacting a 1-phenyl-1-cyclohexen - (11) - yl - 3 - aminopropane of the formula with a 1-phenyl-2-halopropane of the formula or (c) reacting a 1-phenyl-1-cyclohexen-(11)-yl-3-halopropane of the formula with a 1-phenyl-2-aminopropane of the formula or (d) reacting 3-phenyl-3-cyclohexen-(11)-yl-propionaldehyde with a 1-phenyl-2-aminopropane of the Formula (VI) wherein R is a hydrogen atom, and simultaneously or subsequently reducing the C-N double linkage in the condensation product obtained, or (e) reacting phenyl-cyclohexylidene-acetonitrile with a 1-phenyl - N - haloethyl - 2 - aminopropane of the formula wherein R1 is methyl, in the presence of an agent capable of binding a hydrohalic acid, and replacing the nitrile group in the compound obtained by a hydrogen atom either by heating the compound with sodium amide in an inert organic solvent or by hydrolysing it with a strong acid and heating the carboxy compound obtained, or (f) reducing a carboxylic acid amide of the formula by means of a complex metal hydride, and, if desired, methylating a compound obtained by any one of the methods (a) to (d) or (f) at the nitrogen atom by reacting it with a methylating agent and/or converting it into an acid addition salt by reaction with an acid. 3 - Phenyl - 3 - cyclohexen - (11) - yl - propionaldehyde is prepared by reacting phenyl-cyclohexylidene-acetonitrile with chloroacetal to form 3 - phenyl - 3 - cyclohexen - (11) - yl - 3-cyanopropionaldehyde-diethylacetal and treating this compound with sodium amide. Pharmaceutical compositions, having an action on the cardiac and vascular blood circulation, for oral or parenteral administration, comprise a compound of the invention together with a carrier.

公开(公告)号：FI40805B

公开(公告)日：1969-02-28

申请号：FI72663

申请日：1963-04-10

Applicant: HOECHST AG

Inventor： OTT H ,  EHRHART G ,  LINDNER E

IPC: C07C69/732 ,  C07C93/20

Abstract: The invention comprises compounds of the general formula (wherein AC represents a formyl, acetyl or propionyl group) and physiologically tolerable acid addition salts thereof, their preparation by acylating one of the four stereoisomers of 4, 4-diphenyl-6-dimethylaminoheptanol-(3) with a reactive derivative of mandelic acid, the free hydroxy group of which is converted into a formyloxy, acetyloxy or propionyloxy group either before or after the acylation, optionally followed by acid addition salt formation, and pharmaceutical preparations containing them. The compounds of the invention have a beneficial action on the heart and the blood circulation and some of them possess analgesic properties. They may be administered parenterally or orally in the form of pharmaceutical preparations (e.g. tablets or dragees) containing them in admixture or conjunction with a carrier.

公开(公告)号：FI45184B

公开(公告)日：1971-12-31

申请号：FI145166

申请日：1966-06-02

Applicant: HOECHST AG

Inventor： EHRHART G ,  LINDNER E ,  HAERTFELDER G ,  OTT H

IPC: C07C217/62 ,  C07D213/38 ,  C07C91/16

Abstract: Compounds of the general Formula (I) (wherein R1 represents a phenyl, methoxyphenyl or 2-pyridyl group, R2 represents a hydrogen atom or a methyl group and R3 and R4 each represent a C1- 4 alkyl group) and their acid addition salts are prepared by standard methods, e.g. reducing a compound of the Formula (II) (wherein R represents a hydrogen atom) or a salt thereof, or condensing a compound of the Formula (III) with a compound of the Formula (IV) (wherein X represents and reducing the product, optionally followed in either case by salt formation. The preparation of starting materials of Formulae (II) and (IV) is described. The compounds of the invention are useful in the treatment of hypertonia, and may be administered in the form of pharmaceutical preparations containing them in association with a carrier.

公开(公告)号：SE336345B

公开(公告)日：1971-07-05

申请号：SE1128467

申请日：1967-08-09

Applicant: HOECHST AG

Inventor： LEDITSCHKE H ,  EHRHART G ,  RUSCHIG H ,  MEIZNER W

IPC: C07D317/60 ,  C07D13/10

Abstract: (a) Subst. phenylacetamides of formula I R1 and R2 = sat. or unsat. C1-4 aliphatic hydrocarbon. (b) Pharmaceutical prepns. contng. I. (a) Saponification of subst. phenylacetonitriles (II) (b) Reaction of subst. phenylacetic acid III and its reactive functional derivs. with ammonia (c) Dehydration of ammonium salts of subst. phenylacetic acid III (d) Catalytic hydrogenation of cpds. of formula IV in which R3 = H- or benzyl. Sedatives.

公开(公告)号：NO122365B

公开(公告)日：1971-06-21

申请号：NO16324866

申请日：1966-06-01

Applicant: HOECHST AG

Inventor： EHRHART G ,  OTT H

IPC: A61K31/135

Abstract: Novel 1-phenyl-3-aminopropane derivatives of the formula wherein R is hydrogen or methyl and each of R1 and R2 is hydrogen or C1- 4 alkyl, and their physiologically tolerable, acid-addition salts, are prepared by (a) reacting 1-phenyl-1-cyclohexen-(11)-yl-3-aminopropane with a ketone of the formula and simultaneously or subsequently reducing the C-N double bond in the condensation product obtained, or (b) reacting a 1-phenyl-1-cyclohexen - (11) - yl - 3 - aminopropane of the formula with a 1-phenyl-2-halopropane of the formula or (c) reacting a 1-phenyl-1-cyclohexen-(11)-yl-3-halopropane of the formula with a 1-phenyl-2-aminopropane of the formula or (d) reacting 3-phenyl-3-cyclohexen-(11)-yl-propionaldehyde with a 1-phenyl-2-aminopropane of the Formula (VI) wherein R is a hydrogen atom, and simultaneously or subsequently reducing the C-N double linkage in the condensation product obtained, or (e) reacting phenyl-cyclohexylidene-acetonitrile with a 1-phenyl - N - haloethyl - 2 - aminopropane of the formula wherein R1 is methyl, in the presence of an agent capable of binding a hydrohalic acid, and replacing the nitrile group in the compound obtained by a hydrogen atom either by heating the compound with sodium amide in an inert organic solvent or by hydrolysing it with a strong acid and heating the carboxy compound obtained, or (f) reducing a carboxylic acid amide of the formula by means of a complex metal hydride, and, if desired, methylating a compound obtained by any one of the methods (a) to (d) or (f) at the nitrogen atom by reacting it with a methylating agent and/or converting it into an acid addition salt by reaction with an acid. 3 - Phenyl - 3 - cyclohexen - (11) - yl - propionaldehyde is prepared by reacting phenyl-cyclohexylidene-acetonitrile with chloroacetal to form 3 - phenyl - 3 - cyclohexen - (11) - yl - 3-cyanopropionaldehyde-diethylacetal and treating this compound with sodium amide. Pharmaceutical compositions, having an action on the cardiac and vascular blood circulation, for oral or parenteral administration, comprise a compound of the invention together with a carrier.

公开(公告)号：SE319476B

公开(公告)日：1970-01-19

申请号：SE1559265

申请日：1965-12-02

Applicant: HOECHST AG

Inventor： EHRHART G ,  OTT H ,  THER L ,  ALPERMANN H

IPC: C07D211/62 ,  C07D211/64 ,  C07D29/24

Abstract: Novel compounds of formula (I) where R i phenyl or cyclohexene-(1)-yl, R1 is phenyl or cyclohexyl and R2 is C1- 4 alkyl, and acid addition salts thereof are preparable by (a) condensing C6H5.CHR.CH2.CHO with a compound III with simultaneous or subsequent reduction; (b) reacting C6H5.CHR.CH2.CH2.Hal with III in the presence of an acid binder; (c) reacting diphenylmethane with V in the presence of an acid-binder; (d) hydrolysing the nitrile group in a compound of formula (I) in which COOR2 is replaced by CN, followed by esterification; or (e) treating VII with H2 and, if desired, converting resulting free bases into acid addition salts thereof. Cyclohexanone is condensed with benzyl cyanide to give phenyl-cyclohexylidene-acetonitrile. The latter compound and diphenyl acetonitrile are reacted with chloracetaldehyde diethylacetal to give the diethyl acetals of b - phenyl - b - cyclohexen - 1 - yl - b - cyanopropionaldehyd and b ,b -diphenyl-b -cyano-propionaldehyde respectively and the nitrile groups removed by heating with NaNH2 to give b - phenyl - b - cyclohexen - 1 - yl - propionaldehyde diethylacetal and b ,b -diphenylpropionaldehyde dietyl acetal respectively, from which b - phenyl - b - cyclohexen - 1 - yl - propionaldehyde and b ,b - diphenylpropionaldehyde are obtained by acid hydrolysis. 4 - Cyclohexyl - 4 - carbethoxypiperidine is prepared by catalytic hydrogenation of 4-phenyl - 4 - carbethoxypiperidine. The carbonate salt is also isolated. The compounds of formula (I) and their acid addition salts have analgesic properties and may be administered orally or parenterally.

公开(公告)号：SE301814B

公开(公告)日：1968-06-24

申请号：SE931964

申请日：1964-07-31

Applicant: HOECHST AG

Inventor： EHRHART G ,  LINDNER E ,  OTT H

IPC: C07C97/10

公开(公告)号：FI48467B

公开(公告)日：1974-07-01

申请号：FI8767

申请日：1967-01-13

Applicant: HOECHST AG

Inventor： EHRHART G ,  HAERTFELDER G ,  OTT H

IPC: C07D295/02 ,  C07D295/037 ,  C07D29/10