公开(公告)号：US3856910A

公开(公告)日：1974-12-24

申请号：US40914473

申请日：1973-10-24

Applicant: ROUSSEL UCLAF

Inventor： NEDELEC L ,  GUILLAUME J ,  ALLAIS A

IPC: C07D495/04 ,  C07D495/20 ,  A61K27/00

CPC classification number: C07D495/04

Abstract: Novel 4-(alkylaminoalkyl)-(4H)-thieno-(3,2-b)(f)-benzazepines of the formula
WHEREIN R1 and R2 are selected from the group consisting of hydrogen, halogen, -CF3, lower alkoxy optionally substituted, lower alkylthio, lower alkyl, optionally substituted sulfonamido, diloweralkylamino and acylamino wherein the acyl is derived from an organic carboxylic acid of one to 18 carbon atoms, R is selected from the group consisting of hydrogen and lower alkyl, A is alkylene of two to five carbon atoms, optionally substituted by lower alkyl, B is selected from the group consisting of hydrogen, lower alkyl and arloweralkyl, C is selected from the group consisting of lower alkyl and arloweralkyl and B and C taken together are alkylene of two to six carbon atoms optionally interrupted with one or two heteroatoms, Y is selected from the group consisting of hydrogen, hydroxy, lower alkoxy and lower alkanoyloxy, X is hydrogen and taken together with Y forms a carbon-carbon double bond, Z'' is selected from the group consisting of hydrogen and lower alkyl and Z is selected from the group consisting of hydrogen, lower alkyl and lower alkoxy and taken with Y forms a member of the group consisting of 0, lower alkylenedioxy, loweralkylenedithio and thioloweralkyleneoxy and their non-toxic, pharmaceutically acceptable acid addition salts having antidepressant activity with a large therapeutic index and their preparation and novel intermediates.

Abstract translation: 式WHEREIN R1和R2的新型4-（烷基氨基烷基） - [4H] - 噻吩并 - [3,2-b] [f] - 苯并氮杂选自氢，卤素，-CF 3，任选取代的低级烷氧基 ，低级烷硫基，低级烷基，任选取代的磺酰氨基，二低级烷基氨基和酰基氨基，其中酰基衍生自1至18个碳原子的有机羧酸，R选自氢和低级烷基，A是两个至 五个碳原子，任选被低级烷基取代，B选自氢，低级烷基和芳基烷基，C选自低级烷基和低级烷基，B和C一起为二至六碳的亚烷基 任选地被一个或两个杂原子中断的原子，Y选自氢，羟基，低级烷氧基和低级烷酰氧基，X是氢并与Y一起形成碳 - 碳双键，Z'选自 由氢和低级烷基组成的组，Z选自氢，低级烷基和低级烷氧基，Y取代为= 0，低级亚烷基二氧基，低级亚烷基二硫和硫代低级亚烷基氧基团的成员， 具有大的治疗指数的抗抑郁活性的有毒的药学上可接受的酸加成盐及其制备方法和新的中间体。

公开(公告)号：US3766248A

公开(公告)日：1973-10-16

申请号：US3766248D

申请日：1970-03-09

Applicant: ROUSSEL UCLAF

Inventor： NEDELEC L ,  BUCOURT R

IPC: C07D295/096 ,  C07D295/116 ,  C07D311/94 ,  C07J73/00 ,  C07C49/38 ,  C07C69/24 ,  C07C69/78

CPC classification number: C07D295/096 ,  C07C2603/16 ,  C07D295/116 ,  C07D311/94 ,  C07J73/003

Abstract: THIS INVENTION RELATES TO NOVEL SUBSTITUTED TRICYCLIC COMPOUNDS OF THE FORMULA

3-(X-O-),3A-R,7-(O=),6-(HO-CH2-)-1,2,7,8,9,9A-HEXAHYDRO-

3H-BENZ(E)INDENE

WHEREIN R IS ALKYL HAVING FROM 1 TO 6 CARBON ATOMS, X IS SELECTED FROM THE GROUP CONSISTING OF HYDROGEN, ALKYL HAVING FROM 1 TO 5 CARBON ATOMS, ALKENYL HAVING FROM 3 TO 5 CARBON ATOMS, ALKOXYALKYL HAVING FROM 2 TO 5 CARBON ATOMS, ARALKYL HAVING FROM 7 TO 11 CARBON ATOMS, CYCLOALKYLALKYL HAVING FROM 4 TO 11 CARBON ATOMS, ALKYLTHIOALKYL HAVING FROM 2 TO 5 CARBON ATOMS, CYCLOALKYL HAVING FROM 4 TO 7 CARBON ATOMS, AND THE ACYL OF AN ORGANIC CARBOXYLIC ACID HAVING FROM 1 TO 18 CARBON ATOMS, AS WELL AS THE PROCES OF PREPARING THE SAME. THESE COMPOUNDS ARE USEFUL AS INTERMEDIATES IN THE PREPARATION OF 2-OXA STEROIDS OF THE FORMULA

3-(O=),13-R,17-(X-O-)-2-OXAESTRA-4,9,11-TRIENE

WHICH HAVE AN ANABOLIC ACTION COUPLED WITH AN ANDROGENIC ACTION.

公开(公告)号：US3810885A

公开(公告)日：1974-05-14

申请号：US18648371

申请日：1971-10-04

Applicant: ROUSSEL UCLAF

Inventor： BUCOURT R ,  PIERDET A ,  GASC J ,  NEDELEC L

IPC: A61K31/565 ,  A61K31/566 ,  A61K31/567 ,  C07J1/00 ,  C07J41/00 ,  G03B27/62 ,  C07C173/00

CPC classification number: A61K31/567 ,  A61K31/565 ,  A61K31/566 ,  C07J1/00 ,  C07J41/0016 ,  G03B27/62

Abstract: NOVEL 12B-ALKYL-$4.9-GONADIENES OF THE FORMULA

12-X,13-R,17-(R1=)-GONA-4,9-DIEN-3-ONE

AND 12-ALKYL:$4.9.11-GONATREIENES OF THE FORMULA

12-X,13-R,17-(R1=)-GONA-4,9,11-TRIEN-3-ONE

WHEREIN R IS ALKYL OF 1 TO 3 CARBON ATOMS, X IS ALKYL OF 1 TO 3 CARBON ATOMS AND R1 IS SELECTED FROM THE GROUP CONSISTING OF

(R2-O-),(H-); (R2-O-),(R3-); AND (HO-),(R3-)

WHEREIN R2 IS SELECTED FROM THE GROUP CONSISTING OF HYDROCARBYL OF 1 TO 10 CARBON ATOMS AND ACYL OF AN ORGANIC CARBOXYLIC ACID OF 1 TO 18 CARBON ATOMS AND R3 IS SELECTED FROM THE GROUP CONSISTING OF SATURATED HYDROCARBON OF 1 TO 6 CARBON ATOMS AND UNSATURATED HYDROCARBON OF 2 TO 6 CARBON ATOMS WHICH COMPOUNDS POSESS HORMONAL PROPERTIES AND TO TWO NOVEL PROCESSES FOR THEIR PREPARATION AND NOVEL INTERMEDIATES THEREFOR.

公开(公告)号：US3752855A

公开(公告)日：1973-08-14

申请号：US3752855D

申请日：1971-02-03

Applicant: ROUSSEL UCLAF

Inventor： BUCOURT R ,  NEDELEC L

IPC: C07D295/096 ,  C07D295/116 ,  C07J73/00 ,  C07C49/00

CPC classification number: C07D295/096 ,  C07C2603/16 ,  C07D295/116 ,  C07J73/003

Abstract: 2 - OXA - 13B - R-17A-METHYL-$4,9,11-GONATRIENES OF THE FORMULA

3-(O=),17-(R''-O-),17-CH3-ESTRA-4,9,11-TRIENE WHERE C2

IS O AND C18 IS R

WHEREIN R IS SELECTED FROM THE GROUP CONSISTING OF METHYL AND ETHYL AND R'' IS SELECTED FROM THE GROUP CONSISTING OF HYDROGEN, SATURATED ALKYL OF 1 TO 5 CARBON ATOMS WHICH MAY CONTAIN A HETERO OXYGEN ATOM, UNSATURATED ALKYL OF 2 TO 5 CARBON ATOMS, CYCLOALKYL OF 3 TO 5 CARBON ATOMS WHICH MAY CONTAIN A HETERO OXYGEN ATOM, WITH THE PROVISO THAT R IS ETHYL WHEN R'' IS HYDROGEN WHICH COMPOUNDS POSSESS ANABOLIC AND ANDROGENIC ACTIVITY. THE INVENTION ALSO RELATES TO A NOVEL PROCESS AND NOVEL INTERMEDIATES FOR THE PREPARATION OF THE COMPOUNDS OF FORMULA I.

公开(公告)号：US3767676A

公开(公告)日：1973-10-23

申请号：US3767676D

申请日：1972-02-28

Applicant: ROUSSEL UCLAF

Inventor： NEDELEC L ,  GUILLAUME J ,  ALLAIS A

IPC: C07D223/16 ,  C07C205/56 ,  C07D333/28 ,  C07D333/50 ,  C07D333/80 ,  C07D495/00 ,  C07D495/04 ,  C07D495/20 ,  A61K27/00 ,  C07D63/18

CPC classification number: C07D495/04 ,  C07C205/56 ,  C07D333/28

Abstract: NOVEL 9,10-DIHYDRO-(4H)-THIENO-(3,2-B) (F)-BENZAZEPINES OF THE FORMULA

10-A,10-A'',R,R1,R2-9,10-DIHYDRO-4H-THIENO(3,2-B)(F)-

BENZAZEPINE

WHEREIN A AND A'' ARE INDIVIDUALLY SELECTED FROM THE GROUP CONSISTING OF LOWER ALKOXY AND LOWR ALKYLTHIO AND TAKEN TOGETHER ARE SELECTED FROM THE GROUP CONSISTING OF LOWER ALKYLENEDIOXY, LOWWE ALKYLENEDITHIO AND THIOLOWERALKYLENEOXY, R IS SELECTED FROM THE GROUP CONSISTING OF HYDROGEN AND LOWER ALKYL AND R1 AND R2 ARE INDIVIDUALLY SELECTED FROM THE GROUP CONSISTING OF HYDROGEN, HALOGEN, -CF3, OPTIONALLY SUBSTITUTED LOWER ALKOXY, LOWER ALKYLTHIO, OPTIONALLY SUBSTITUTED SULFONAMIDO, DILOWERALKYL AMINO, AND ACYLAMINO WHERE THE ACYL IS DERIVED FROM AN ORGANIC CARBOXYLIC ACID OF 1 TO 18 CARBON ATOMS WHICH ARE INTERMEDIATES FOR 4-(ALKYLAMINOALKYL)-(4H)-THIENO(3,2-B) (F)-BENZAZEPINES HAVING ANTIDEPRESSANT ACTIVITY AND THE PROCESS FOR THE THEIR PREPARATION AND NOVEL INTERMEDIATES.

公开(公告)号：US3714203A

公开(公告)日：1973-01-30

申请号：US3714203D

申请日：1969-07-07

Applicant: ROUSSEL UCLAF

Inventor： NEDELEC L ,  TORELLI V

IPC: B05B1/14 ,  B05B17/04 ,  C07D303/32 ,  C07D303/40 ,  C07J73/00 ,  C07D5/10

CPC classification number: C07D303/32 ,  C07D303/40 ,  C07J73/003

Abstract: 1-OXA-A-Nor steroids of the formula

WHEREIN R is selected from the group consisting of hydrogen, acyl of an organic carboxylic acid of one to 18 carbon atoms and alkyl of one to five carbon atoms which may be further substituted with an aryl, alkoxy and alkylthio which have antiandrogenic activity and their preparation and use.

Abstract translation: 1-OXA-A-型甾体，式WHEREIN R选自氢，1至18个碳原子的有机羧酸的酰基和1至5个碳原子的烷基，可以进一步被芳基取代 ，烷氧基和烷硫基，其具有抗雄激素活性及其制备和用途。

公开(公告)号：US3708474A

公开(公告)日：1973-01-02

申请号：US3708474D

申请日：1971-02-03

Applicant: ROUSSEL UCLAF

Inventor： NEDELEC L ,  GASC J

IPC: C07J1/00 ,  C07J75/00 ,  C07C169/22 ,  C07C173/00

CPC classification number: C07J1/00 ,  C07J75/00

Abstract: 2A,2B,17A A-TRIMETHYL - 13B - ALKYL-$4,9,11-GONATRIENE-17BOL-3-ONES OF THE FORMULA

2,2,17-TRI(H3C-),4-R1,7-R2,17-(Z-O-),18-R-GONA-4,9,11-

TRIEN-3-ONE

WHEREIN Z IS HYDROGEN, ALKYL OF 1 TO 6 CARBON ATOMS OR TETRAHYDROPYRANYL, R IS ALKYL OF 1 TO 4 CARBON ATOMS, R1 IS SELECTED FROM THE GROUP CONSISTING OF HYDROGEN, HYDROXY, LOWER ALKANOYLOXY OF 1 TO 7 CARBON ATOMS AND HALOGEN, AND R2 IS HYDROGEN ALKYL OF 1 TO 4 CARBON ATOMS HAVING ANTI-ANDROGENIC ACTIVITY AND THEIR PREPARATION.

公开(公告)号：US3787445A

公开(公告)日：1974-01-22

申请号：US3787445D

申请日：1972-02-28

Applicant: ROUSSEL UCLAF

Inventor： NEDELEC L ,  GUILLAUME J ,  ALLAIS A

IPC: C07D223/16 ,  A61K31/55 ,  C07D333/50 ,  C07D495/04 ,  C07D495/20 ,  A61K27/00 ,  C07D63/18

CPC classification number: C07D495/04

Abstract: NOVEL 4-(ALKYAMINOALKYL)-(4H)-THIENO-(3,2-B)(F)BENZAZEPINES OF THE FORMULA

4-(B-N(-C)-A-),9-X,9-Z'',10-Y,10-Z,R,R1,R2-9,10-DIHYDRO-

4H-THIENO(3,2-B)-4-BENZAZEPINE

WHEREIN R1 AND R2 ARE SELECTED FROM THE GROUP CONSISTING OF HYDROGE, HALOGEN, -CF3, LOWER ALOXY OPTIONALLY SUBSTITUTED, LOWER ALKYLTHIO, LOWER ALKYL, OPTIONALLY SUBSTITUTED SULFONAMIDE, DILOWERALKYLAMINO AND ACYLAMINO WHEREIN THE ACYL IS DERIVED FROM AN ORGANIC CARBOXYLIC ACID OF 1 TO 18 CARBON ATOMS, R IS SELECTED FROM THE GROUP CONSISTING OF HYDROGEN AND LOWER ALKYL, A IS ALKYLENE OF 2 TO 5 CARBON ATOMS, OPTIONALLY SUBSTITUTED BY LOWER ALKYL, B IS SELECTED FROM THE GROUP CONSISTING OF HYDROGEN, LOWER ALKYL AND ARLOWERALKYL, C IS SELECTED FROM THE GROUP CONSISTING OF LOWER ALKYL AND ARLOWERALKYL AND B AND C TAKEN TOGETHER ARE ALKYLENE OR 2 TO 6 CARBON TOMS OPTIONALLY INTERRUPTED WITH 1 OR 2 HETEROATOMS, Y IS SELECTED FROM THE GROUP CONSISTING OF HYDROGEN, HYDROXY, LOWER ALKOXY AND LOWER ALKANOYLOXY, X IS HYDROGEN AND TAKEN TOGETHER WITH Y FORMS A CARBON-CARBON DOUBLE BOND, Z'' IS SELECTED FROM THE GROUP CONSISTING OF HYDROGEN AND LOWER ALKYL AND Z IS SELECTED FROM THE GROUP CONSISTING OF HYDROGN, LOWER ALKYL AND LOWER ALKOXY AND TAKEN WITH Y FORMS A MEMBER OF THE GROUP CONSISTING OF =O, LOWER ALKYLENEDIOXY, LOWER ALKYLENEDITHIO AND THIOLOWERALKYLENEOXY AND THEIR NON-TOXIC, PHARMACEUTICALY ACCEPTABLE ACID ADDITION SALTS HAVING ANTIDEPRESSANT ACTIVITY WITH A LARGE THERAPEUTIC INDEX AND THEIR PREPARATION AND NOVEL INTERMEDIATES.

公开(公告)号：US3719691A

公开(公告)日：1973-03-06

申请号：US3719691D

申请日：1970-07-27

Applicant: ROUSSEL UCLAF

Inventor： BUCOURT R ,  NEDELEC L ,  GASC J

IPC: A61K31/567 ,  C07J1/00 ,  C07C167/14

CPC classification number: A61K31/567 ,  C07J1/00

Abstract: A novel process for the preparation of 7 Alpha -methyl-13 Beta R-17 Alpha -X-17 Beta -OY- Delta 4,9,11-gonatriene-3-ones of the formula

WHEREIN R is lower alkyl of one to four carbon atoms, X is saturated or unsaturated, substituted or unsubstituted, straight or branched aliphatic hydrocarbon of one to four carbon atoms and Y is selected from the group consisting of hydrogen and acyl of an organic carboxylic acid of one to 18 carbon atoms and novel intermediates formed therein.