EA032311B1 - Тетрагидро-пиридо[3,4-b]индоловые модуляторы эстрогеновых рецепторов и их применение - Google Patents

Info

Publication number

EA032311B1

EA032311B1 EA201791239A EA201791239A EA032311B1 EA 032311 B1 EA032311 B1 EA 032311B1 EA 201791239 A EA201791239 A EA 201791239A EA 201791239 A EA201791239 A EA 201791239A EA 032311 B1 EA032311 B1 EA 032311B1

Authority

EA

Eurasian Patent Office

Prior art keywords

methyl

phenyl

fluoro

indol

azetidin

Prior art date

2014-12-18

Links

• Espacenet
• Global Dossier
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• 239000002834 estrogen receptor modulator Substances 0.000 title claims abstract description 6
• CFTOTSJVQRFXOF-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole Chemical compound N1C2=CC=CC=C2C2=C1CNCC2 CFTOTSJVQRFXOF-UHFFFAOYSA-N 0.000 title description 16
• -1 tetrahydro-pyrido[3,4-b]indol-1-yl compounds Chemical class 0.000 claims abstract description 354
• 150000001875 compounds Chemical class 0.000 claims abstract description 328
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 62
• 150000003839 salts Chemical class 0.000 claims abstract description 46
• 201000010099 disease Diseases 0.000 claims abstract description 36
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 25
• 230000000694 effects Effects 0.000 claims abstract description 23
• 108010038795 estrogen receptors Proteins 0.000 claims abstract description 20
• 230000001419 dependent effect Effects 0.000 claims abstract description 11
• 102000015694 estrogen receptors Human genes 0.000 claims abstract description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 286
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 97
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 96
• RERZNCLIYCABFS-UHFFFAOYSA-N harmaline Chemical compound C1CN=C(C)C2=C1C1=CC=C(OC)C=C1N2 RERZNCLIYCABFS-UHFFFAOYSA-N 0.000 claims description 82
• 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 80
• 206010028980 Neoplasm Diseases 0.000 claims description 70
• 201000011510 cancer Diseases 0.000 claims description 59
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 57
• JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims description 56
• HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims description 54
• 229910052740 iodine Inorganic materials 0.000 claims description 54
• 238000011282 treatment Methods 0.000 claims description 33
• 206010006187 Breast cancer Diseases 0.000 claims description 31
• 208000026310 Breast neoplasm Diseases 0.000 claims description 30
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 30
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 29
• 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 28
• 208000035475 disorder Diseases 0.000 claims description 26
• NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims description 23
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
• 125000000623 heterocyclic group Chemical group 0.000 claims description 23
• 125000003118 aryl group Chemical group 0.000 claims description 22
• 125000004432 carbon atom Chemical group C* 0.000 claims description 21
• 229920006395 saturated elastomer Polymers 0.000 claims description 21
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims description 17
• 229940088597 hormone Drugs 0.000 claims description 16
• 230000001225 therapeutic effect Effects 0.000 claims description 16
• 239000002246 antineoplastic agent Substances 0.000 claims description 15
• 239000005556 hormone Substances 0.000 claims description 15
• 229910052739 hydrogen Inorganic materials 0.000 claims description 15
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 15
• 125000004429 atom Chemical group 0.000 claims description 14
• 229940127089 cytotoxic agent Drugs 0.000 claims description 13
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
• 238000002560 therapeutic procedure Methods 0.000 claims description 13
• 229910052794 bromium Inorganic materials 0.000 claims description 12
• 239000003085 diluting agent Substances 0.000 claims description 12
• 102000005962 receptors Human genes 0.000 claims description 12
• 108020003175 receptors Proteins 0.000 claims description 12
• 125000006413 ring segment Chemical group 0.000 claims description 12
• 229960001603 tamoxifen Drugs 0.000 claims description 12
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
• 125000001072 heteroaryl group Chemical group 0.000 claims description 11
• VWUXBMIQPBEWFH-WCCTWKNTSA-N Fulvestrant Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3[C@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)CC2=C1 VWUXBMIQPBEWFH-WCCTWKNTSA-N 0.000 claims description 10
• 229960002258 fulvestrant Drugs 0.000 claims description 10
• FDPKMJDUXJFKOI-UHFFFAOYSA-N azetidin-3-amine Chemical compound NC1CNC1 FDPKMJDUXJFKOI-UHFFFAOYSA-N 0.000 claims description 9
• 125000002393 azetidinyl group Chemical group 0.000 claims description 8
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
• 125000003566 oxetanyl group Chemical group 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 229910052698 phosphorus Inorganic materials 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 7
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 7
• 206010014759 Endometrial neoplasm Diseases 0.000 claims description 7
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 7
• HWDVTQAXQJQROO-UHFFFAOYSA-N cyclopropylazanide Chemical compound [NH-]C1CC1 HWDVTQAXQJQROO-UHFFFAOYSA-N 0.000 claims description 7
• LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 7
• 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 7
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
• 125000006763 (C3-C9) cycloalkyl group Chemical group 0.000 claims description 6
• AGRIQBHIKABLPJ-UHFFFAOYSA-N 1-Pyrrolidinecarboxaldehyde Chemical compound O=CN1CCCC1 AGRIQBHIKABLPJ-UHFFFAOYSA-N 0.000 claims description 6
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• 206010014733 Endometrial cancer Diseases 0.000 claims description 6
• 206010033128 Ovarian cancer Diseases 0.000 claims description 6
• 206010060862 Prostate cancer Diseases 0.000 claims description 6
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• 229960003881 letrozole Drugs 0.000 claims description 6
• HPJKCIUCZWXJDR-UHFFFAOYSA-N letrozole Chemical compound C1=CC(C#N)=CC=C1C(N1N=CN=C1)C1=CC=C(C#N)C=C1 HPJKCIUCZWXJDR-UHFFFAOYSA-N 0.000 claims description 6
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
• 239000001301 oxygen Chemical group 0.000 claims description 6
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 6
• 239000011593 sulfur Substances 0.000 claims description 6
• 229960000575 trastuzumab Drugs 0.000 claims description 6
• BFYIZQONLCFLEV-DAELLWKTSA-N Aromasine Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)C2=C1 BFYIZQONLCFLEV-DAELLWKTSA-N 0.000 claims description 5
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 5
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
• 239000013543 active substance Substances 0.000 claims description 5
• 229960002932 anastrozole Drugs 0.000 claims description 5
• 125000002619 bicyclic group Chemical group 0.000 claims description 5
• 229960000255 exemestane Drugs 0.000 claims description 5
• 201000005202 lung cancer Diseases 0.000 claims description 5
• 208000020816 lung neoplasm Diseases 0.000 claims description 5
• 206010046766 uterine cancer Diseases 0.000 claims description 5
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
• ZQZFYGIXNQKOAV-OCEACIFDSA-N Droloxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=C(O)C=CC=1)\C1=CC=C(OCCN(C)C)C=C1 ZQZFYGIXNQKOAV-OCEACIFDSA-N 0.000 claims description 4
• 208000002495 Uterine Neoplasms Diseases 0.000 claims description 4
• YBBLVLTVTVSKRW-UHFFFAOYSA-N anastrozole Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2N=CN=C2)=C1 YBBLVLTVTVSKRW-UHFFFAOYSA-N 0.000 claims description 4
• 230000000903 blocking effect Effects 0.000 claims description 4
• 238000002512 chemotherapy Methods 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 125000002950 monocyclic group Chemical group 0.000 claims description 4
• 239000011574 phosphorus Chemical group 0.000 claims description 4
• 238000001959 radiotherapy Methods 0.000 claims description 4
• 238000001356 surgical procedure Methods 0.000 claims description 4
• ROBVIMPUHSLWNV-UHFFFAOYSA-N aminoglutethimide Chemical compound C=1C=C(N)C=CC=1C1(CC)CCC(=O)NC1=O ROBVIMPUHSLWNV-UHFFFAOYSA-N 0.000 claims description 3
• 229960003437 aminoglutethimide Drugs 0.000 claims description 3
• 229960000397 bevacizumab Drugs 0.000 claims description 3
• 125000004122 cyclic group Chemical group 0.000 claims description 3
• 229950004203 droloxifene Drugs 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 229910052736 halogen Inorganic materials 0.000 claims description 3
• 150000002367 halogens Chemical class 0.000 claims description 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
• 229960004622 raloxifene Drugs 0.000 claims description 3
• GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• CLPFFLWZZBQMAO-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1N2C=NC=C2CCC1 CLPFFLWZZBQMAO-UHFFFAOYSA-N 0.000 claims description 2
• DODQJNMQWMSYGS-QPLCGJKRSA-N 4-[(z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-1-phenylbut-1-en-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 DODQJNMQWMSYGS-QPLCGJKRSA-N 0.000 claims description 2
• 206010055113 Breast cancer metastatic Diseases 0.000 claims description 2
• IHGLINDYFMDHJG-UHFFFAOYSA-N [2-(4-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(OC)=CC=C1C(CCC1=CC=CC=C11)=C1C(=O)C(C=C1)=CC=C1OCCN1CCCC1 IHGLINDYFMDHJG-UHFFFAOYSA-N 0.000 claims description 2
• 238000004891 communication Methods 0.000 claims description 2
• 229950011548 fadrozole Drugs 0.000 claims description 2
• 229960004421 formestane Drugs 0.000 claims description 2
• OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 claims description 2
• RQZAXGRLVPAYTJ-GQFGMJRRSA-N megestrol acetate Chemical compound C1=C(C)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 RQZAXGRLVPAYTJ-GQFGMJRRSA-N 0.000 claims description 2
• 229960004296 megestrol acetate Drugs 0.000 claims description 2
• 229960002087 pertuzumab Drugs 0.000 claims description 2
• 229960004641 rituximab Drugs 0.000 claims description 2
• 229950000212 trioxifene Drugs 0.000 claims description 2
• XLMPPFTZALNBFS-INIZCTEOSA-N vorozole Chemical compound C1([C@@H](C2=CC=C3N=NN(C3=C2)C)N2N=CN=C2)=CC=C(Cl)C=C1 XLMPPFTZALNBFS-INIZCTEOSA-N 0.000 claims description 2
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 2
• 229940126214 compound 3 Drugs 0.000 claims 2
• 239000013256 coordination polymer Substances 0.000 claims 2
• IEXUMDBQLIVNHZ-YOUGDJEHSA-N (8s,11r,13r,14s,17s)-11-[4-(dimethylamino)phenyl]-17-hydroxy-17-(3-hydroxypropyl)-13-methyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C1=CC(N(C)C)=CC=C1[C@@H]1C2=C3CCC(=O)C=C3CC[C@H]2[C@H](CC[C@]2(O)CCCO)[C@@]2(C)C1 IEXUMDBQLIVNHZ-YOUGDJEHSA-N 0.000 claims 1
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
• JLERVPBPJHKRBJ-UHFFFAOYSA-N LY 117018 Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCC3)=CC=2)C2=CC=C(O)C=C2S1 JLERVPBPJHKRBJ-UHFFFAOYSA-N 0.000 claims 1
• IWEQQRMGNVVKQW-OQKDUQJOSA-N Toremifene citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 IWEQQRMGNVVKQW-OQKDUQJOSA-N 0.000 claims 1
• 239000004914 cyclooctane Substances 0.000 claims 1
• 230000003054 hormonal effect Effects 0.000 claims 1
• 208000018819 hormone-resistant breast carcinoma Diseases 0.000 claims 1
• 150000002460 imidazoles Chemical class 0.000 claims 1
• 229950011093 onapristone Drugs 0.000 claims 1
• KHRUFOVTDYNBBK-UHFFFAOYSA-N pyrrolidin-1-yl(pyrrol-1-yl)methanone Chemical compound C1=CC=CN1C(=O)N1CCCC1 KHRUFOVTDYNBBK-UHFFFAOYSA-N 0.000 claims 1
• 229960004167 toremifene citrate Drugs 0.000 claims 1
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• 238000000034 method Methods 0.000 abstract description 78
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• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 146
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 134
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 117
• XAXXTYXMWOFKLW-UHFFFAOYSA-N [C-]1=CC=[NH+]1 Chemical compound [C-]1=CC=[NH+]1 XAXXTYXMWOFKLW-UHFFFAOYSA-N 0.000 description 102
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
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• 210000004027 cell Anatomy 0.000 description 60
• 238000005481 NMR spectroscopy Methods 0.000 description 58
• 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 description 58
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• 239000000243 solution Substances 0.000 description 46
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 42
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 42
• 125000001424 substituent group Chemical group 0.000 description 42
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• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 37
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• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 24
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• GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 16
• 239000003886 aromatase inhibitor Substances 0.000 description 15
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 14
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