Non-steroidal progesterone receptor modulators

1 . Compounds of the general formula I

R 1 and R 2 are independently of one another a hydrogen atom, a linear or nonlinear, branched or unbranched C 1 -C 5 -alkyl group, further forming together with the C atom of the chain a ring having a total of 3-7 members,

R 3 is a radical C≡C—R a , where

R a is a hydrogen or a C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 3 -C 10 -cycloalkyl, heterocycloalkyl optionally substituted one or more times, identically or differently, by K, or an aryl or heteroaryl optionally substituted one or more times, identically or differently by L,

K is a cyano, halogen, hydroxy, nitro, —C(O)R b , CO 2 R b , —O—R b , —S—R b , SO 2 NR c R d , —C(O)—NR c R d ,

—OC(O)—NR c R d , —C═NOR b —NR c R d or C 3 -C 10 -cycloalkyl, heterocycloalkyl optionally substituted one or more times, identically or differently, by M, or aryl or heteroaryl optionally substituted one or more times by L,

L is C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 1 -C 6 -perfluoroalkyl, C 1 -C 6 -perfluoroalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, (CH 2 ) p —C 3 -C 10 -cycloalkyl, (CH 2 ) p -heterocycloalkyl, (CH 2 ) p CN, (CH 2 ) p Hal, (CH 2 ) p NO 2 , (CH 2 ) p —C 6 -C 12 -aryl, (CH 2 ) p -heteroaryl,

—(CH 2 ) p PO 3 (R b ) 2 , —(CH 2 ) p NR c R d , —(CH 2 ) p NR e COR b , —(CH 2 ) p NR e CSR b , —(CH 2 ) p NR e S(O)R b , —(CH 2 ) p NR e S(O) 2 R b , —(CH 2 ) p NR e CONR c R d , —(CH 2 ) p NR e COOR b , —(CH 2 ) p NR e C(NH)NR c R d , —(CH 2 ) p NR e CSNR c R d , —(CH 2 ) p NR e S(O)NR c R d , —(CH 2 ) p NR e S(O) 2 NR c R d , —(CH 2 ) p COR b , —(CH 2 ) p CSR b , —(CH 2 ) p S(O)R b , —(CH 2 ) p S(O)(NH)R b , —(CH 2 ) p S(O) 2 R b , —(CH 2 ) p S(O) 2 NR c R d , —(CH 2 ) p SO 2 OR b , —(CH 2 ) p CO 2 R b , —(CH 2 ) p CONR c R d ,

—(CH 2 ) p CSNR c R d , —(CH 2 ) p OR b , —(CH 2 ) p SR b , —(CH 2 ) p CR b (OH)—R e , —(CH 2 ) p —C═NOR b ,

—O—(CH 2 ), —O—, —O—(CH 2 ), —CH 2 —, —O—CH═CH— or —(CH 2 ) n+2 —, where n is 1 or 2, and the terminal oxygen atoms and/or carbon atoms are linked to directly adjacent ring carbon atoms,

M is C 1 -C 6 -alkyl or a group —COR b , CO 2 R b , —O—R b , or —NR c R d , where

R b is a hydrogen or a C 1 -C 6 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 3 -C 10 -cycloalkyl, C 6 -C 12 -aryl or C 1 -C 3 -perfluoroalkyl and

R c and R d are independently of one another a hydrogen, C 1 -C 6 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 3 -C 10 -cycloalkyl, C 6 -C 12 -aryl, C(O)R b or a hydroxy group, where if

R c is a hydroxy group, then R d can only be a hydrogen, a C 1 -C 6 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 3 -C 10 -cycloalkyl or C 6 -C 12 -aryl and vice versa, and

R e is a hydrogen, C 1 -C 6 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 3 -C 10 -cycloalkyl or C 6 -C 12 -aryl, and p can be a number from 0-6,

or

R 3 is a radical C═C—R g R h , where

R g and R h are independently of one another a hydrogen or a C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl or C 2 -C 8 -alkynyl optionally substituted one or more times, identically or differently, by X, in which

X is a cyano, halogen, hydroxy, nitro, —C(O)R b , CO 2 R b , —O—R b , —C(O)—NR c R d , —NR c R d with the meanings already mentioned before for R b , R c and R d , and

R 4 is a hydrogen atom, a methyl or an ethyl group or a partly or completely fluorinated C 1 -C 3 -alkyl group,

A is a mono- or bicyclic carbocyclic or heterocyclic aromatic ring which may optionally be substituted one or more times by C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 1 -C 6 -perfluoroalkyl, C 1 -C 6 -perfluoroalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, (CH 2 ) p —C 3 -C 10 -cycloalkyl, (CH 2 ) p -heterocycloalkyl, (CH 2 ) p CN, (CH 2 ) p Hal, (CH 2 ) p NO 2 , (CH 2 ) p —C 6 -C 12 -aryl, (CH 2 ) p -heteroaryl, —(CH 2 ) p PO 3 (R b ) 2 , —(CH 2 ) p NR c R d , —(CH 2 ) p NR e COR b , —(CH 2 ) p NR e CSR b , —(CH 2 ) p NR e S(O)R b , —(CH 2 ) NR e S(O) 2 R b , —(CH 2 ) p NR e CONR c R d , —(CH 2 ) p NR e COOR b , —(CH 2 ) p NR e C(NH)NR c R d , —(CH 2 ) p NR e CSNR c R d , —(CH 2 ) p NR e S(O)NR c R d , —(CH 2 ) p NR e S(O) 2 NR c R d , (CH 2 ) p COR b , —(CH 2 ) p CSR b , —(CH 2 ) p S(O)R b , —(CH 2 ) p S(O)(NH)R b , —(CH 2 ) p S(O) 2 R b , —(CH 2 ) p S(O) 2 NR c R d , —(CH 2 ) p SO 2 OR b , —(CH 2 ) p CO 2 R b , —(CH 2 ) p CONR c R d , —(CH 2 ) p CSNR c R d , —(CH 2 ) p OR b , —(CH 2 ) p SR b , —(CH 2 ) p CR b (OH)—R d , —(CH 2 ) p —C═NOR b , —O—(CH 2 ), —O—, —O—(CH 2 ), —CH 2 —, —O—CH═CH— or —(CH 2 ) n+2 —, where n is 1 or 2, and the terminal oxygen atoms and/or carbon atoms are linked to directly adjacent ring carbon atoms, or

A is a radical —CO 2 R b , C(O)NR c R d , COR b ,

or

A is an alkenyl group —CR 5 ═CR 6 R 7 , where

R 5 , R 6 and R 7 are identical or different and are independently of one another hydrogen atoms, halogen atoms, aryl radicals or an unsubstituted or partly or completely fluorinated C 1 -C 5 -alkyl group, or

A is an alkynyl group —C≡CR 5 , with the meaning stated above for R 5 , and

B is a carbonyl or a CH 2 group

and their pharmaceutically acceptable salts.

2 . Compounds according to claim 1 , in which R 1 and R 2 are preferably a hydrogen atom, a methyl or ethyl group.

3 . Compounds according to claim 1 , in which R 1 and R 2 preferably form together with the C atom of the chain a ring having a total of 3-7 members.

4 . Compounds according to claim 1 , in which R 3 is preferably alkenyl, alkynyl, arylalkynyl, heteroarylalkynyl, cycloalkylalkynyl, heterocycloalkylalkynyl.

5 . Compounds according to claim 1 , in which R 3 is preferably a vinyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, hydroxypropynyl, hydroxybutynyl, 3-hydroxy-3-methylbutynyl, hydroxypentynyl, carboxypropynyl, t-butylcarboxypropynyl, phenylethynyl, (hydroxyphenyl)ethynyl, (methoxyphenyl)ethynyl, (dimethylaminophenyl)ethynyl, (methylphenyl)ethynyl, (cyanophenyl)ethynyl, (trifluoromethyl)ethynyl, (diphenyl)ethynyl, (nitrophenyl)ethynyl, (tert-butylphenyl)ethynyl, (acetylphenyl)ethynyl, (acetoxyphenyl)ethynyl, (carboxyphenyl)ethynyl or a benzylethynyl group.

6 . Compounds according to claim 1 , in which A is preferably an aromatic ring.

7 . Compounds according to claim 1 , in which A is preferably a phenyl or naphthyl radical.

8 . Compounds according to claim 7 , in which A is preferably an unsubstituted or optionally mono- or polysubstituted phenyl radical.

9 . Compounds according to claim 8 , where the phenyl radical is preferably substituted by one or two halogen atoms or one trifluoromethyl group.

10 . Compounds according to claim 9 , in which the halogen atoms are preferably chlorine and/or fluorine.

11 . Compounds according to claim 1 , in which A is preferably a phenyl ring substituted by —O—(CH 2 ) n —O— or —O—(CH 2 ) n —CH 2 —, where the respectively directly adjacent ring carbon atoms are linked.

12 . Compounds according to claim 1 , in which R 4 is a hydrogen atom, a methyl or a trifluoromethyl radical.

13 . Compounds according to claim 1 , namely

Racemic or

No.

enantiomer

R3

  1   2   3

rac −+

  4   5   6

rac +−

  7   8   9

rac +−

 10  11  12

rac +−

 13  14  15

rac +−

 16  17  18

rac +−

 19  20  21

rac +−

 22  23  24

rac +−

 25  26  27

rac +−

 28  29  30

rac +−

 31  32  33

rac +−

 34  35  36

rac +−

 37  38  39

rac +−

 40  41  42

rac +−

 43  44  45

rac +−

 46  47  48

rac +−

 49  50  51

rac +−

 52  53  54

rac −+

 55  56  57

rac +−

 58  59  60

rac +−

 61  62  63

rac +−

 64  65  66

rac +−

 67  68  69

rac +−

 70  71  72

rac +−

 73  74  75

rac +−

 76  77  78

rac +−

 79  80  81

rac +−

 82  83  84

rac +−

 85  86  87

rac +−

 88  89  90

rac +−

 91  92  93

rac +−

 94  95  96

rac +−

 97  98  99

rac +−

 100  191  102

rac +−

 103  104  105

rac +−

 106  107  108

rac −+

 109  110  111

rac +−

 112  113  114

rac +−

 115  116  117

rac +−

 118  119  120

rac +−

 121  122  123

rac +−

 124  125  126

rac +−

 127  128  129

rac +−

 130  131  132

rac +−

 133  134  135

rac +−

 136  137  138

rac +−

 139  140  141

rac +−

 142  143  144

rac +−

 145  146  147

rac +−

 148  149  150

rac +−

 151  152  153

rac +−

 154  155  156

rac +−

 157  158  159

rac +−

 160  161  162

rac +−

 163  164  165

rac +−

 166  167  168

rac +−

 169  170  171

rac −+

 172  173  174

rac +−

 175  176  177

rac +−

 178  179  180

rac +−

 181  182  183

rac +−

 184  185  186

rac +−

 187  188  189

rac +−

 190  191  192

rac +−

 193  194  195

rac +−

 196  197  198

rac +−

 199  200  201

rac +−

 202  203  204

rac +−

 205  206  207

rac +−

 208  209  210

rac +−

 211  212  213

rac +−

 214  215  216

rac +−

 217  218  219

rac +−

 220  221  222

rac +−

 223  224  225

rac +−

 226  227  228

rac +−

 229  230  231

rac +−

 232  233  234

rac −+

 235  236  237

rac +−

 238  239  240

rac +−

 241  242  243

rac +−

 244  245  246

rac +−

 247  248  249

rac +−

 250  251  252

rac +−

 253  254  255

rac +−

 256  257  258

rac +−

 259  260  261

rac +−

 262  263  264

rac +−

 265  266  267

rac +−

 268  269  270

rac +−

 271  272  273

rac +−

 274  275  276

rac +−

 277  278  279

rac +−

 280  281  282

rac +−

 283  284  285

rac +−

 286  287  288

rac +−

 289  290  291

rac +−

 292  293  294

rac +−

 295  296  297

rac −+

 298  299  300

rac +−

 301  302  303

rac +−

 304  305  306

rac +−

 307  308  309

rac +−

 310  311  312

rac +−

 313  314  315

rac +−

 316  317  317

rac +−

 319  320  321

rac +−

 322  323  324

rac +−

 325  326  327

rac +−

 328  329  330

rac +−

 331  332  333

rac +−

 334  335  336

rac +−

 337  338  339

rac +−

 340  341  342

rac +−

 343  344  345

rac +−

 346  347  348

rac +−

 349  350  351

rac +−

 352  353  354

rac +−

 355  356  357

rac +−

 358  359  360

rac −+

 361  362  363

rac +−

 364  365  366

rac +−

 367  368  369

rac +−

 370  371  372

rac +−

 373  374  375

rac +−

 376  377  378

rac +−

 379  380  381

rac +−

 382  383  384

rac +−

 385  386  387

rac +−

 388  389  390

rac +−

 391  392  393

rac +−

 394  395  396

rac +−

 397  398  399

rac +−

 400  401  402

rac +−

 403  404  405

rac +−

 406  407  408

rac +−

 409  410  411

rac +−

 412  413  414

rac +−

 415  416  417

rac +−

 418  419  420

rac +−

 421  422  423

rac −+

 424  425  426

rac +−

 427  428  429

rac +−

 430  431  432

rac +−

 433  434  435

rac +−

 436  437  438

rac +−

 439  440  441

rac +−

 442  443  444

rac +−

 445  446  447

rac +−

 448  449  450

rac +−

 451  452  453

rac +−

 454  455  456

rac +−

 457  458  459

rac +−

 460  461  462

rac +−

 463  464  465

rac +−

 466  467  468

rac +−

 469  470  471

rac +−

 472  473  474

rac +−

 475  476  477

rac +−

 478  479  480

rac +−

 481  482  483

rac +−

 484  485  486

rac −+

 487  488  489

rac +−

 490  491  492

rac +−

 493  494  495

rac +−

 496  497  498

rac +−

 499  500  501

rac +−

 502  503  504

rac +−

 505  506  507

rac +−

 508  509  510

rac +−

 511  512  513

rac +−

 514  515  516

rac +−

 517  518  519

rac +−

 520  521  522

rac +−

 523  524  525

rac +−

 526  527  528

rac +−

 529  530  531

rac +−

 532  533  534

rac +−

 535  536  537

rac +−

 538  539  540

rac +−

 541  542  543

rac +−

 544  545  546

rac +−

 547  548  549

rac −+

 550  551  552

rac +−

 553  554  555

rac +−

 556  557  558

rac +−

 559  560  561

rac +−

 562  563  564

rac +−

 565  566  567

rac +−

 568  569  570

rac +−

 571  572  573

rac +−

 574  575  576

rac +−

 577  578  579

rac +−

 580  581  582

rac +−

 583  584  585

rac +−

 586  587  588

rac +−

 589  590  591

rac +−

 592  593  594

rac +−

 595  596  597

rac +−

 598  599  600

rac +−

 601  602  603

rac +−

 604  605  606

rac +−

 607  608  609

rac +−

 610  611  612

rac −+

 613  614  615

rac +−

 616  617  618

rac +−

 619  620  621

rac +−

 622  623  624

rac +−

 625  626  627

rac +−

 628  629  630

rac +−

 631  632  633

rac +−

 634  635  636

rac +−

 637  638  639

rac +−

 640  641  642

rac +−

 643  644  645

rac +−

 646  647  648

rac +−

 649  650  651

rac +−

 652  653  654

rac +−

 655  656  657

rac +−

 658  659  660

rac +−

 661  662  663

rac +−

 664  665  666

rac +−

 667  668  669

rac +−

 670  671  672

rac +−

 673  674  675

rac −+

 676  677  678

rac +−

 679  680  681

rac +−

 682  683  684

rac +−

 685  686  687

rac +−

 688  689  690

rac +−

 691  692  693

rac +−

 694  695  696

rac +−

 697  698  699

rac +−

 700  701  702

rac +−

 703  704  705

rac +−

 706  707  708

rac +−

 709  710  711

rac +−

 712  713  714

rac +−

 715  716  717

rac +−

 718  719  720

rac +−

 721  722  723

rac +−

 724  725  726

rac +−

 727  728  729

rac +−

 730  731  732

rac +−

 733  734  735

rac +−

 736  737  738

rac −+

 739  740  741

rac +−

 742  743  744

rac +−

 745  746  747

rac +−

 748  749  750

rac +−

 751  752  753

rac +−

 754  755  756

rac +−

 757  758  759

rac +−

 760  761  762

rac +−

 763  764  765

rac +−

 766  767  768

rac +−

 769  770  771

rac +−

 772  773  774

rac +−

 775  776  777

rac +−

 778  779  780

rac +−

 781  782  783

rac +−

 784  785  786

rac +−

 787  788  789

rac +−

 790  791  792

rac +−

 793  794  795

rac +−

 796  797  798

rac +−

 799  800  801

rac −+

 802  803  804

rac +−

 805  806  807

rac +−

 808  809  810

rac +−

 811  812  813

rac +−

 814  815  816

rac +−

 817  818  819

rac +−

 820  821  822

rac +−

 823  824  825

rac +−

 826  827  828

rac +−

 829  830  831

rac +−

 832  833  834

rac +−

 835  836  837

rac +−

 838  839  840

rac +−

 841  842  843

rac +−

 844  845  846

rac +−

 847  848  849

rac +−

 850  851  852

rac +−

 853  854  855

rac +−

 856  857  858

rac +−

 859  860  861

rac +−

 862  863  864

rac −+

 865  866  867

rac +−

 868  869  870

rac +−

 871  872  873

rac +−

 874  875  876

rac +−

 877  878  879

rac +−

 880  881  882

rac +−

 883  884  885

rac +−

 886  887  888

rac +−

 889  890  891

rac +−

 892  893  894

rac +−

 895  896  897

rac +−

 898  899  900

rac +−

 901  902  903

rac +−

 904  905  906

rac +−

 907  908  909

rac +−

 910  911  912

rac +−

 913  914  915

rac +−

 916  917  918

rac +−

 919  920  921

rac +−

 922  923  924

rac +−

 925  926  927

rac −+

 928  929  930

rac +−

 931  932  933

rac +−

 934  935  936

rac +−

 937  938  939

rac +−

 940  941  942

rac +−

 943  944  945

rac +−

 946  947  948

rac +−

 949  950  951

rac +−

 952  953  954

rac +−

 955  956  957

rac +−

 958  959  960

rac +−

 961  962  963

rac +−

 964  965  966

rac +−

 967  968  969

rac +−

 970  971  972

rac +−

 973  974  975

rac +−

 976  977  978

rac +−

 979  980  981

rac +−

 982  983  984

rac +−

 985  986  987

rac +−

 988  989  990

rac −+

 991  992  993

rac +−

 994  995  996

rac +−

 997  998  999

rac +−

1000 1001 1002

rac +−

1003 1004 1005

rac +−

1006 1007 1008

rac +−

1009 1010 1011

rac +−

1012 1013 1014

rac +−

1015 1016 1017

rac +−

1018 1019 1020

rac +−

1021 1022 1023

rac +−

1024 1025 1026

rac +−

1027 1028 1029

rac +−

1030 1031 1032

rac +−

1033 1034 1035

rac +−

1036 1037 1038

rac +−

1039 1040 1041

rac +−

1042 1043 1044

rac +−

1045 1046 1047

rac +−

1048 1049 1050

rac +−

1051 1052 1053

rac −+

1054 1055 1056

rac +−

1057 1058 1059

rac +−

1060 1061 1062

rac +−

1063 1064 1065

rac +−

1066 1067 1068

rac +−

1069 1070 1071

rac +−

1072 1073 1074

rac +−

1075 1076 1077

rac +−

1078 1079 1080

rac +−

1081 1082 1083

rac +−

1084 1085 1086

rac +−

1087 1088 1089

rac +−

1090 1091 1092

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14 . Pharmaceutical composition comprising at least one compound of the general formula I according to claim 1 and, where appropriate, at least one further active ingredient together with pharmaceutically suitable excipients and/or carriers.

15 . Pharmaceutical composition according to claim 14 , where the further active ingredient is a SERM (selective estrogen receptor modulator), an aromatase inhibitor, an antiestrogen or a prostaglandin.

16 . Pharmaceutical composition according to claim 14 , where the active ingredient may be tamoxifen, 5-(4-{5-[(RS)-(4,4,5,5,5-pentafluoropentyl)sulphinyl]pentyloxy}phenyl) -6-phenyl-8,9-dihydro-7H-benzocyclohepten-2-ol, ICI 182 780 (7alpha-[9-(4,4,5,5-pentafluoropentylsulphinyl)nonyl]estra-1,3,5(10)-triene-3,17beta-diol), 11beta-fluoro-7alpha-[5-(methyl {3-[(4,4,5,5,5-pentafluoropentyl)sulphanyl]propyl}amino)pentyl]estra-1,3,5(10)-triene -3,17beta-diol, 11beta-fluoro-7alpha-{5-[methyl(7,7,8,8,9,9,10,10,10-nonafluorodecyl)amino]pentyl}estra-1,3,5(10)-triene-3,17beta-diol, 11beta-fluoro-17alpha-methyl -7alpha-{5-[methyl(8,8,9,9,9-pentafluorononyl)amino]pentyl}estra-1,3,5(10)-triene -3,17beta-diol, clomifen, raloxifen, fadrozole, formestane, letrozole, anastrozole or atamestane.

17 . Use of compounds according to claim 1 for producing a medicament.

18 . Use of compounds according to claim 17 for producing a medicament for the therapy and prophylaxis of gynaecological disorders such as endometriosis, leiomyomas of the uterus, dysfunctional bleeding and dysmenorrhoea.

19 . Use of compounds according to claim 17 for producing a medicament for the therapy and prophylaxis of hormone-dependent tumours.

20 . Use of compounds according to claim 17 for producing a medicament for the therapy and prophylaxis of breast carcinomas.

21 . Use of compounds according to claim 17 for producing a medicament for the therapy and prophylaxis of endometrial carcinoma.

22 . Use of compounds according to claim 17 for producing a medicament for the therapy and prophylaxis of ovarian carcinomas.

23 . Use of compounds according to claim 17 for producing a medicament for the therapy and prophylaxis of prostate carcinomas.

24 . Use of compounds according to claim 17 for producing a medicament for female hormone replacement therapy.

25 . Use of compounds according to claim 17 for female fertility control.

26 . Process for the selective addition of lithium alkynyl and magnesium haloalkynyl compounds onto a keto amide.