公开(公告)号：CS9104095A3

公开(公告)日：1992-04-15

申请号：CS409591

申请日：1991-12-27

Applicant: HOECHST AG

Inventor： URBACH HANSJORG DR ,  HENNING RAINER DR ,  TEETZ VOLKER DR ,  GEIGER ROLF PROF DR ,  BECKER REINHARD DR ,  GAUL HOLGER

IPC: A61K38/55 ,  A61K31/40 ,  A61K31/403 ,  A61K31/404 ,  A61K38/00 ,  A61P7/10 ,  A61P9/08 ,  A61P9/12 ,  C07D209/02 ,  C07D209/08 ,  C07D209/32 ,  C07D209/34 ,  C07D209/42 ,  C07D209/52 ,  C07D215/22 ,  C07D215/227 ,  C07K1/02 ,  C07K1/113 ,  C07K5/02 ,  C07K5/06

CPC classification number: C07D215/227 ,  A61K38/00 ,  C07D209/08 ,  C07D209/34 ,  C07D209/42 ,  C07D209/52 ,  C07K5/0222

公开(公告)号：FI80675B

公开(公告)日：1990-03-30

申请号：FI883456

申请日：1988-07-21

Applicant: HOECHST AG

Inventor： URBACH HANSJOERG ,  HENNING RAINER ,  TEETZ VOLKER ,  GEIGER ROLF ,  BECKER REINHARD ,  GAUL HOLGER

IPC: C07D20060101 ,  C07D209/42 ,  C07D209/52

公开(公告)号：HU194167B

公开(公告)日：1988-01-28

申请号：HU465382

申请日：1982-12-28

Applicant: HOECHST AG

Inventor： URBACH HANSJOERG ,  HENNING RAINER ,  GEIGER ROLF ,  TEETZ VOLKER ,  BECKER REINHARD ,  GAUL HOLGER

IPC: A61K38/55 ,  A61K31/40 ,  A61K31/403 ,  A61K31/404 ,  A61K38/00 ,  A61P7/10 ,  A61P9/08 ,  A61P9/12 ,  C07D209/02 ,  C07D209/08 ,  C07D209/32 ,  C07D209/34 ,  C07D209/42 ,  C07D209/52 ,  C07D215/22 ,  C07D215/227 ,  C07K1/02 ,  C07K1/113 ,  C07K5/02 ,  C07K5/06

Abstract: 1. Claims for the Contracting states ; BE, CH, DE, FR, GB, IT, Li, Lu, NL, SE A compound of the formula I see diagramm : EP0084164,P21,F7 in which the hydrogen atoms on the bridgehead C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n denotes 0, 1 or 2, R1 denotes methyl, R2 denotes hydrogen, (C1 -C4 )-alkyl or benzyl, Y denotes hydrogen or hydroxyl, Z denotes hydrogen or Y and Z together denote oxygen and X denotes phenyl, and its physiologically acceptable salts. 1. Claims for the Contracting state : Austria A process for the preparation of the compounds of the formula I see diagramm : EP0084164,P24,F4 in which the hydrogen atoms on the bridgehead C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n denotes 0, 1 or 2, R1 denotes methyl, R2 denotes hydrogen, (C1 -C4 )-alkyl or benzyl, Y denotes hydrogen or hydroxyl, Z denotes hydrogen or Y and Z together denote oxygen and X denotes phenyl, and its physiologically acceptable salts, which a) comprises reacting a compound of the formula II see diagramm : EP0084164,P24,F6 wherein R1 , R2 , X, Y and Z have the meanings as in formula I, with a compound of the formula III see diagramm : EP0084164,P25,F1 in which the H atoms on the C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n denotes 0, 1 or 2 and W denotes a radical which can be cleaved off by hydrogenolysis or by acid, and subsequently splitting off the radical W and, if appropriate, the radical R2 to form the free carboxyl groups, or b) for the preparation of compounds of the formula I, in which Y and Z together denote oxygen, comprises b1 ) reacting a compound of the formula IV see diagramm : EP0084164,P25,F3 in which the H atoms on the C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n and R1 have the meanings as in formula I and W has the meaning as in formula III, with a compound of the formula V, R2 O2 C-CH = CH-CO-X wherein R2 and X have the meanings as in formula I, and subsequently splitting off the radical W and, if appropriate, also the radical R2 to form the free carboxyl groups, or, b2 ) reacting a compound of the formula IV mentioned under b1 ) with a compound of the general formula VI, wherein R2 has the meaning as in formula I, and with a compound of the general formula VII OHC-CO2 R2 X-CO-CH3 wherein X has the meaning as in formula I, subsequently splitting off the radical W and, if appropriate, the radical R2 to form the free carboxyl group, or c) for the preparation of compounds of the formula I, in which Y and Z each denote hydrogen, comprises c1 ) reacting a compound of the formula IV mentioned under b1 ) with a compound of the formula VIII see diagramm : EP0084164,P25,F2 wherein R2 and X have the meanings as in formula I, reducing the Schiff's bases obtained and subsequently splitting off the radical W and, if appropriate, the radical R2 to form the free carboxyl groups, or c2 ) catalytically reducing a compound of the formula I in which Y and Z together denote oxygen, with hydrogen, or d) for the preparation of compounds of the formula I, in which Y denotes hydroxyl and Z denotes hydrogen, comprises reducing a compound of the formula I, in which Y and Z together denote oxygen, catalytically with hydrogen or with a reducing agent, such as sodium borohydride, and, if appropriate, converting the compounds obtained according to (a)-(d) into their physiologically acceptable salts.

公开(公告)号：NO156786C

公开(公告)日：1987-11-25

申请号：NO824394

申请日：1982-12-28

Applicant: HOECHST AG

Inventor： URBACH HANSJORG ,  HENNING RAINER ,  TEETZ VOLKER ,  GEIGER ROLF ,  BECKER REINHARD ,  GAUL HOLGER

IPC: A61K38/55 ,  A61K31/40 ,  A61K31/403 ,  A61K31/404 ,  A61K38/00 ,  A61P7/10 ,  A61P9/08 ,  A61P9/12 ,  C07D209/02 ,  C07D209/08 ,  C07D209/32 ,  C07D209/34 ,  C07D209/42 ,  C07D209/52 ,  C07D215/22 ,  C07D215/227 ,  C07K1/02 ,  C07K1/113 ,  C07K5/02 ,  C07K5/06 ,  C07D209/12

Abstract: 1. Claims for the Contracting states ; BE, CH, DE, FR, GB, IT, Li, Lu, NL, SE A compound of the formula I see diagramm : EP0084164,P21,F7 in which the hydrogen atoms on the bridgehead C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n denotes 0, 1 or 2, R1 denotes methyl, R2 denotes hydrogen, (C1 -C4 )-alkyl or benzyl, Y denotes hydrogen or hydroxyl, Z denotes hydrogen or Y and Z together denote oxygen and X denotes phenyl, and its physiologically acceptable salts. 1. Claims for the Contracting state : Austria A process for the preparation of the compounds of the formula I see diagramm : EP0084164,P24,F4 in which the hydrogen atoms on the bridgehead C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n denotes 0, 1 or 2, R1 denotes methyl, R2 denotes hydrogen, (C1 -C4 )-alkyl or benzyl, Y denotes hydrogen or hydroxyl, Z denotes hydrogen or Y and Z together denote oxygen and X denotes phenyl, and its physiologically acceptable salts, which a) comprises reacting a compound of the formula II see diagramm : EP0084164,P24,F6 wherein R1 , R2 , X, Y and Z have the meanings as in formula I, with a compound of the formula III see diagramm : EP0084164,P25,F1 in which the H atoms on the C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n denotes 0, 1 or 2 and W denotes a radical which can be cleaved off by hydrogenolysis or by acid, and subsequently splitting off the radical W and, if appropriate, the radical R2 to form the free carboxyl groups, or b) for the preparation of compounds of the formula I, in which Y and Z together denote oxygen, comprises b1 ) reacting a compound of the formula IV see diagramm : EP0084164,P25,F3 in which the H atoms on the C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n and R1 have the meanings as in formula I and W has the meaning as in formula III, with a compound of the formula V, R2 O2 C-CH = CH-CO-X wherein R2 and X have the meanings as in formula I, and subsequently splitting off the radical W and, if appropriate, also the radical R2 to form the free carboxyl groups, or, b2 ) reacting a compound of the formula IV mentioned under b1 ) with a compound of the general formula VI, wherein R2 has the meaning as in formula I, and with a compound of the general formula VII OHC-CO2 R2 X-CO-CH3 wherein X has the meaning as in formula I, subsequently splitting off the radical W and, if appropriate, the radical R2 to form the free carboxyl group, or c) for the preparation of compounds of the formula I, in which Y and Z each denote hydrogen, comprises c1 ) reacting a compound of the formula IV mentioned under b1 ) with a compound of the formula VIII see diagramm : EP0084164,P25,F2 wherein R2 and X have the meanings as in formula I, reducing the Schiff's bases obtained and subsequently splitting off the radical W and, if appropriate, the radical R2 to form the free carboxyl groups, or c2 ) catalytically reducing a compound of the formula I in which Y and Z together denote oxygen, with hydrogen, or d) for the preparation of compounds of the formula I, in which Y denotes hydroxyl and Z denotes hydrogen, comprises reducing a compound of the formula I, in which Y and Z together denote oxygen, catalytically with hydrogen or with a reducing agent, such as sodium borohydride, and, if appropriate, converting the compounds obtained according to (a)-(d) into their physiologically acceptable salts.

公开(公告)号：NO156786B

公开(公告)日：1987-08-17

申请号：NO824394

申请日：1982-12-28

Applicant: HOECHST AG

Inventor： URBACH HANSJOERG ,  HENNING RAINER ,  TEETZ VOLKER ,  GEIGER ROLF ,  BECKER REINHARD ,  GAUL HOLGER

IPC: A61K38/55 ,  A61K31/40 ,  A61K31/403 ,  A61K31/404 ,  A61K38/00 ,  A61P7/10 ,  A61P9/08 ,  A61P9/12 ,  C07D209/02 ,  C07D209/08 ,  C07D209/32 ,  C07D209/34 ,  C07D209/42 ,  C07D209/52 ,  C07D215/22 ,  C07D215/227 ,  C07K1/02 ,  C07K1/113 ,  C07K5/02 ,  C07K5/06 ,  C07D209/12

Abstract: 1. Claims for the Contracting states ; BE, CH, DE, FR, GB, IT, Li, Lu, NL, SE A compound of the formula I see diagramm : EP0084164,P21,F7 in which the hydrogen atoms on the bridgehead C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n denotes 0, 1 or 2, R1 denotes methyl, R2 denotes hydrogen, (C1 -C4 )-alkyl or benzyl, Y denotes hydrogen or hydroxyl, Z denotes hydrogen or Y and Z together denote oxygen and X denotes phenyl, and its physiologically acceptable salts. 1. Claims for the Contracting state : Austria A process for the preparation of the compounds of the formula I see diagramm : EP0084164,P24,F4 in which the hydrogen atoms on the bridgehead C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n denotes 0, 1 or 2, R1 denotes methyl, R2 denotes hydrogen, (C1 -C4 )-alkyl or benzyl, Y denotes hydrogen or hydroxyl, Z denotes hydrogen or Y and Z together denote oxygen and X denotes phenyl, and its physiologically acceptable salts, which a) comprises reacting a compound of the formula II see diagramm : EP0084164,P24,F6 wherein R1 , R2 , X, Y and Z have the meanings as in formula I, with a compound of the formula III see diagramm : EP0084164,P25,F1 in which the H atoms on the C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n denotes 0, 1 or 2 and W denotes a radical which can be cleaved off by hydrogenolysis or by acid, and subsequently splitting off the radical W and, if appropriate, the radical R2 to form the free carboxyl groups, or b) for the preparation of compounds of the formula I, in which Y and Z together denote oxygen, comprises b1 ) reacting a compound of the formula IV see diagramm : EP0084164,P25,F3 in which the H atoms on the C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n and R1 have the meanings as in formula I and W has the meaning as in formula III, with a compound of the formula V, R2 O2 C-CH = CH-CO-X wherein R2 and X have the meanings as in formula I, and subsequently splitting off the radical W and, if appropriate, also the radical R2 to form the free carboxyl groups, or, b2 ) reacting a compound of the formula IV mentioned under b1 ) with a compound of the general formula VI, wherein R2 has the meaning as in formula I, and with a compound of the general formula VII OHC-CO2 R2 X-CO-CH3 wherein X has the meaning as in formula I, subsequently splitting off the radical W and, if appropriate, the radical R2 to form the free carboxyl group, or c) for the preparation of compounds of the formula I, in which Y and Z each denote hydrogen, comprises c1 ) reacting a compound of the formula IV mentioned under b1 ) with a compound of the formula VIII see diagramm : EP0084164,P25,F2 wherein R2 and X have the meanings as in formula I, reducing the Schiff's bases obtained and subsequently splitting off the radical W and, if appropriate, the radical R2 to form the free carboxyl groups, or c2 ) catalytically reducing a compound of the formula I in which Y and Z together denote oxygen, with hydrogen, or d) for the preparation of compounds of the formula I, in which Y denotes hydroxyl and Z denotes hydrogen, comprises reducing a compound of the formula I, in which Y and Z together denote oxygen, catalytically with hydrogen or with a reducing agent, such as sodium borohydride, and, if appropriate, converting the compounds obtained according to (a)-(d) into their physiologically acceptable salts.

公开(公告)号：PH18918A

公开(公告)日：1985-11-06

申请号：PH28321

申请日：1982-12-27

Applicant: HOECHST AG

Inventor： URBACH HANSJORG ,  HENNING RAINER ,  GEIGER ROLF ,  TEETZ VOLKER ,  BECKER REINHARD ,  GAUL HOLGER

IPC: A61K38/55 ,  A61K31/40 ,  A61K31/403 ,  A61K31/404 ,  A61K38/00 ,  A61P7/10 ,  A61P9/08 ,  A61P9/12 ,  C07D209/02 ,  C07D209/08 ,  C07D209/32 ,  C07D209/34 ,  C07D209/42 ,  C07D209/52 ,  C07D215/22 ,  C07D215/227 ,  C07K1/02 ,  C07K1/113 ,  C07K5/02 ,  C07K5/06 ,  C07D211/00 ,  C07D211/06

Abstract: 1. Claims for the Contracting states ; BE, CH, DE, FR, GB, IT, Li, Lu, NL, SE A compound of the formula I see diagramm : EP0084164,P21,F7 in which the hydrogen atoms on the bridgehead C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n denotes 0, 1 or 2, R1 denotes methyl, R2 denotes hydrogen, (C1 -C4 )-alkyl or benzyl, Y denotes hydrogen or hydroxyl, Z denotes hydrogen or Y and Z together denote oxygen and X denotes phenyl, and its physiologically acceptable salts. 1. Claims for the Contracting state : Austria A process for the preparation of the compounds of the formula I see diagramm : EP0084164,P24,F4 in which the hydrogen atoms on the bridgehead C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n denotes 0, 1 or 2, R1 denotes methyl, R2 denotes hydrogen, (C1 -C4 )-alkyl or benzyl, Y denotes hydrogen or hydroxyl, Z denotes hydrogen or Y and Z together denote oxygen and X denotes phenyl, and its physiologically acceptable salts, which a) comprises reacting a compound of the formula II see diagramm : EP0084164,P24,F6 wherein R1 , R2 , X, Y and Z have the meanings as in formula I, with a compound of the formula III see diagramm : EP0084164,P25,F1 in which the H atoms on the C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n denotes 0, 1 or 2 and W denotes a radical which can be cleaved off by hydrogenolysis or by acid, and subsequently splitting off the radical W and, if appropriate, the radical R2 to form the free carboxyl groups, or b) for the preparation of compounds of the formula I, in which Y and Z together denote oxygen, comprises b1 ) reacting a compound of the formula IV see diagramm : EP0084164,P25,F3 in which the H atoms on the C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n and R1 have the meanings as in formula I and W has the meaning as in formula III, with a compound of the formula V, R2 O2 C-CH = CH-CO-X wherein R2 and X have the meanings as in formula I, and subsequently splitting off the radical W and, if appropriate, also the radical R2 to form the free carboxyl groups, or, b2 ) reacting a compound of the formula IV mentioned under b1 ) with a compound of the general formula VI, wherein R2 has the meaning as in formula I, and with a compound of the general formula VII OHC-CO2 R2 X-CO-CH3 wherein X has the meaning as in formula I, subsequently splitting off the radical W and, if appropriate, the radical R2 to form the free carboxyl group, or c) for the preparation of compounds of the formula I, in which Y and Z each denote hydrogen, comprises c1 ) reacting a compound of the formula IV mentioned under b1 ) with a compound of the formula VIII see diagramm : EP0084164,P25,F2 wherein R2 and X have the meanings as in formula I, reducing the Schiff's bases obtained and subsequently splitting off the radical W and, if appropriate, the radical R2 to form the free carboxyl groups, or c2 ) catalytically reducing a compound of the formula I in which Y and Z together denote oxygen, with hydrogen, or d) for the preparation of compounds of the formula I, in which Y denotes hydroxyl and Z denotes hydrogen, comprises reducing a compound of the formula I, in which Y and Z together denote oxygen, catalytically with hydrogen or with a reducing agent, such as sodium borohydride, and, if appropriate, converting the compounds obtained according to (a)-(d) into their physiologically acceptable salts.

公开(公告)号：GR78413B

公开(公告)日：1984-09-27

申请号：GR820170162

申请日：1982-12-23

Applicant: HOECHST AG

Inventor： URBACH HANSJORG DR ,  HENNING RAINER DR ,  TEETZ VOLKER DR ,  GEIGER ROLF PROF DR ,  BECKER REINHARD DR ,  GAUL HOLGER

IPC: A61K38/55 ,  A61K31/40 ,  A61K31/403 ,  A61K31/404 ,  A61K38/00 ,  A61P7/10 ,  A61P9/08 ,  A61P9/12 ,  C07D209/02 ,  C07D209/08 ,  C07D209/32 ,  C07D209/34 ,  C07D209/42 ,  C07D209/52 ,  C07D215/22 ,  C07D215/227 ,  C07K1/02 ,  C07K1/113 ,  C07K5/02 ,  C07K5/06

Abstract: 1. Claims for the Contracting states ; BE, CH, DE, FR, GB, IT, Li, Lu, NL, SE A compound of the formula I see diagramm : EP0084164,P21,F7 in which the hydrogen atoms on the bridgehead C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n denotes 0, 1 or 2, R1 denotes methyl, R2 denotes hydrogen, (C1 -C4 )-alkyl or benzyl, Y denotes hydrogen or hydroxyl, Z denotes hydrogen or Y and Z together denote oxygen and X denotes phenyl, and its physiologically acceptable salts. 1. Claims for the Contracting state : Austria A process for the preparation of the compounds of the formula I see diagramm : EP0084164,P24,F4 in which the hydrogen atoms on the bridgehead C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n denotes 0, 1 or 2, R1 denotes methyl, R2 denotes hydrogen, (C1 -C4 )-alkyl or benzyl, Y denotes hydrogen or hydroxyl, Z denotes hydrogen or Y and Z together denote oxygen and X denotes phenyl, and its physiologically acceptable salts, which a) comprises reacting a compound of the formula II see diagramm : EP0084164,P24,F6 wherein R1 , R2 , X, Y and Z have the meanings as in formula I, with a compound of the formula III see diagramm : EP0084164,P25,F1 in which the H atoms on the C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n denotes 0, 1 or 2 and W denotes a radical which can be cleaved off by hydrogenolysis or by acid, and subsequently splitting off the radical W and, if appropriate, the radical R2 to form the free carboxyl groups, or b) for the preparation of compounds of the formula I, in which Y and Z together denote oxygen, comprises b1 ) reacting a compound of the formula IV see diagramm : EP0084164,P25,F3 in which the H atoms on the C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n and R1 have the meanings as in formula I and W has the meaning as in formula III, with a compound of the formula V, R2 O2 C-CH = CH-CO-X wherein R2 and X have the meanings as in formula I, and subsequently splitting off the radical W and, if appropriate, also the radical R2 to form the free carboxyl groups, or, b2 ) reacting a compound of the formula IV mentioned under b1 ) with a compound of the general formula VI, wherein R2 has the meaning as in formula I, and with a compound of the general formula VII OHC-CO2 R2 X-CO-CH3 wherein X has the meaning as in formula I, subsequently splitting off the radical W and, if appropriate, the radical R2 to form the free carboxyl group, or c) for the preparation of compounds of the formula I, in which Y and Z each denote hydrogen, comprises c1 ) reacting a compound of the formula IV mentioned under b1 ) with a compound of the formula VIII see diagramm : EP0084164,P25,F2 wherein R2 and X have the meanings as in formula I, reducing the Schiff's bases obtained and subsequently splitting off the radical W and, if appropriate, the radical R2 to form the free carboxyl groups, or c2 ) catalytically reducing a compound of the formula I in which Y and Z together denote oxygen, with hydrogen, or d) for the preparation of compounds of the formula I, in which Y denotes hydroxyl and Z denotes hydrogen, comprises reducing a compound of the formula I, in which Y and Z together denote oxygen, catalytically with hydrogen or with a reducing agent, such as sodium borohydride, and, if appropriate, converting the compounds obtained according to (a)-(d) into their physiologically acceptable salts.

公开(公告)号：ZA829523B

公开(公告)日：1983-10-26

申请号：ZA829523

申请日：1982-12-28

Applicant: HOECHST AG

Inventor： URBACH HANSJOERG ,  HENNING RAINER ,  TEETZ VOLKER ,  BECKER REINHARD ,  GEIGER ROLF ,  GAUL HOLGER

IPC: A61K38/00 ,  C07D209/08 ,  C07D209/34 ,  C07D209/42 ,  C07D209/52 ,  C07D215/22 ,  C07D215/227 ,  C07D

公开(公告)号：DE3210701A1

公开(公告)日：1983-10-06

申请号：DE3210701

申请日：1982-03-24

Applicant: HOECHST AG

Inventor： TEETZ VOLKER DR ,  GAUL HOLGER

IPC: A61K38/00 ,  C07D209/08 ,  C07D209/34 ,  C07D209/42 ,  C07D209/52 ,  C07D215/22 ,  C07D215/227

Abstract: The invention relates to a process for the preparation of compounds of the formula I in which n represents an integer from 4 to 13 and R represents hydrogen, which is characterised in that enamines of cyclic ketones are reacted with N-acylated beta -halo- alpha -aminopropionic acid esters or with acrylic acid esters, then a ring closure is performed with acylamine and ester cleavage, and the intermediates of the formula VIIa or VIIb defined in the description resulting in this way are reduced to compounds of the formula I. The invention furthermore relates to intermediates of the formulae VIIa and VIIb.

公开(公告)号：FI824474L

公开(公告)日：1983-06-30

申请号：FI824474

申请日：1982-12-27

Applicant: HOECHST AG

Inventor： URBACH HANSJOERG ,  HENNING RAINER ,  TEETZ VOLKER ,  GEIGER ROLF ,  BECKER REINHARD ,  GAUL HOLGER

IPC: A61K38/55 ,  A61K31/40 ,  A61K31/403 ,  A61K31/404 ,  A61K38/00 ,  A61P7/10 ,  A61P9/08 ,  A61P9/12 ,  C07D209/02 ,  C07D209/08 ,  C07D209/32 ,  C07D209/34 ,  C07D209/42 ,  C07D209/52 ,  C07D215/22 ,  C07D215/227 ,  C07K1/02 ,  C07K1/113 ,  C07K5/02 ,  C07K5/06 ,  C07D

Abstract: 1. Claims for the Contracting states ; BE, CH, DE, FR, GB, IT, Li, Lu, NL, SE A compound of the formula I see diagramm : EP0084164,P21,F7 in which the hydrogen atoms on the bridgehead C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n denotes 0, 1 or 2, R1 denotes methyl, R2 denotes hydrogen, (C1 -C4 )-alkyl or benzyl, Y denotes hydrogen or hydroxyl, Z denotes hydrogen or Y and Z together denote oxygen and X denotes phenyl, and its physiologically acceptable salts. 1. Claims for the Contracting state : Austria A process for the preparation of the compounds of the formula I see diagramm : EP0084164,P24,F4 in which the hydrogen atoms on the bridgehead C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n denotes 0, 1 or 2, R1 denotes methyl, R2 denotes hydrogen, (C1 -C4 )-alkyl or benzyl, Y denotes hydrogen or hydroxyl, Z denotes hydrogen or Y and Z together denote oxygen and X denotes phenyl, and its physiologically acceptable salts, which a) comprises reacting a compound of the formula II see diagramm : EP0084164,P24,F6 wherein R1 , R2 , X, Y and Z have the meanings as in formula I, with a compound of the formula III see diagramm : EP0084164,P25,F1 in which the H atoms on the C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n denotes 0, 1 or 2 and W denotes a radical which can be cleaved off by hydrogenolysis or by acid, and subsequently splitting off the radical W and, if appropriate, the radical R2 to form the free carboxyl groups, or b) for the preparation of compounds of the formula I, in which Y and Z together denote oxygen, comprises b1 ) reacting a compound of the formula IV see diagramm : EP0084164,P25,F3 in which the H atoms on the C atoms 3a and (6+n)a have the trans configuration relative to one another and wherein n and R1 have the meanings as in formula I and W has the meaning as in formula III, with a compound of the formula V, R2 O2 C-CH = CH-CO-X wherein R2 and X have the meanings as in formula I, and subsequently splitting off the radical W and, if appropriate, also the radical R2 to form the free carboxyl groups, or, b2 ) reacting a compound of the formula IV mentioned under b1 ) with a compound of the general formula VI, wherein R2 has the meaning as in formula I, and with a compound of the general formula VII OHC-CO2 R2 X-CO-CH3 wherein X has the meaning as in formula I, subsequently splitting off the radical W and, if appropriate, the radical R2 to form the free carboxyl group, or c) for the preparation of compounds of the formula I, in which Y and Z each denote hydrogen, comprises c1 ) reacting a compound of the formula IV mentioned under b1 ) with a compound of the formula VIII see diagramm : EP0084164,P25,F2 wherein R2 and X have the meanings as in formula I, reducing the Schiff's bases obtained and subsequently splitting off the radical W and, if appropriate, the radical R2 to form the free carboxyl groups, or c2 ) catalytically reducing a compound of the formula I in which Y and Z together denote oxygen, with hydrogen, or d) for the preparation of compounds of the formula I, in which Y denotes hydroxyl and Z denotes hydrogen, comprises reducing a compound of the formula I, in which Y and Z together denote oxygen, catalytically with hydrogen or with a reducing agent, such as sodium borohydride, and, if appropriate, converting the compounds obtained according to (a)-(d) into their physiologically acceptable salts.