CA2695852C - Cyclic amine compounds - Google Patents
Cyclic amine compounds Download PDFInfo
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- CA2695852C CA2695852C CA2695852A CA2695852A CA2695852C CA 2695852 C CA2695852 C CA 2695852C CA 2695852 A CA2695852 A CA 2695852A CA 2695852 A CA2695852 A CA 2695852A CA 2695852 C CA2695852 C CA 2695852C
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- -1 Cyclic amine compounds Chemical class 0.000 title claims description 94
- 150000001875 compounds Chemical class 0.000 claims abstract description 303
- 125000001424 substituent group Chemical group 0.000 claims abstract description 154
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 83
- 125000005843 halogen group Chemical group 0.000 claims abstract description 76
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 68
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 67
- 150000003839 salts Chemical class 0.000 claims abstract description 58
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 34
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 25
- 150000001924 cycloalkanes Chemical class 0.000 claims abstract description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 104
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 53
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 37
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 27
- 239000008177 pharmaceutical agent Substances 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 22
- 150000001721 carbon Chemical group 0.000 claims description 21
- 210000003205 muscle Anatomy 0.000 claims description 21
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
- 210000002307 prostate Anatomy 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 238000011321 prophylaxis Methods 0.000 claims description 16
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 12
- 206010006895 Cachexia Diseases 0.000 claims description 11
- 208000036119 Frailty Diseases 0.000 claims description 11
- 206010003549 asthenia Diseases 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 11
- 230000037396 body weight Effects 0.000 claims description 10
- 208000001132 Osteoporosis Diseases 0.000 claims description 9
- 208000035475 disorder Diseases 0.000 claims description 9
- 206010058359 Hypogonadism Diseases 0.000 claims description 8
- 230000007423 decrease Effects 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 239000000849 selective androgen receptor modulator Substances 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003623 enhancer Substances 0.000 claims description 6
- 230000001965 increasing effect Effects 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 206010020880 Hypertrophy Diseases 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 229940124011 Androgen receptor agonist Drugs 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 210000001519 tissue Anatomy 0.000 claims description 4
- 206010002027 Amyotrophy Diseases 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 229940083324 Selective androgen receptor modulator Drugs 0.000 claims description 2
- DARLYICVLXBOGY-CPCISQLKSA-N 2-chloro-4-[(2s,3s)-3-hydroxy-2-methyl-5-oxopyrrolidin-1-yl]benzonitrile Chemical compound C[C@H]1[C@@H](O)CC(=O)N1C1=CC=C(C#N)C(Cl)=C1 DARLYICVLXBOGY-CPCISQLKSA-N 0.000 claims 2
- SHAOFUWVZYWFRX-HJIKLVIJSA-N 2-chloro-4-[(2s,3s,4s)-2-ethyl-3-hydroxy-4-methyl-5-oxopyrrolidin-1-yl]benzonitrile Chemical compound CC[C@H]1[C@@H](O)[C@H](C)C(=O)N1C1=CC=C(C#N)C(Cl)=C1 SHAOFUWVZYWFRX-HJIKLVIJSA-N 0.000 claims 2
- ROVSKDDUAFHOGB-WDEREUQCSA-N 2-chloro-4-[(4r,5s)-5-ethyl-3,3-difluoro-4-hydroxy-2-oxopyrrolidin-1-yl]benzonitrile Chemical compound CC[C@H]1[C@@H](O)C(F)(F)C(=O)N1C1=CC=C(C#N)C(Cl)=C1 ROVSKDDUAFHOGB-WDEREUQCSA-N 0.000 claims 2
- LJQBTMVNFWIQQC-RYUDHWBXSA-N 4-[(2s,3s)-2-ethyl-3-hydroxy-5-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound CC[C@H]1[C@@H](O)CC(=O)N1C1=CC=C(C#N)C(C(F)(F)F)=C1 LJQBTMVNFWIQQC-RYUDHWBXSA-N 0.000 claims 2
- SADHCJVAYWBWFE-CMPLNLGQSA-N 4-[(4r,5s)-5-ethyl-3,3-difluoro-4-hydroxy-2-oxopyrrolidin-1-yl]-2-methoxybenzonitrile Chemical compound CC[C@H]1[C@@H](O)C(F)(F)C(=O)N1C1=CC=C(C#N)C(OC)=C1 SADHCJVAYWBWFE-CMPLNLGQSA-N 0.000 claims 2
- 230000009471 action Effects 0.000 abstract description 17
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 16
- 125000004430 oxygen atom Chemical group O* 0.000 abstract description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 12
- 229910052717 sulfur Inorganic materials 0.000 abstract description 12
- 125000004434 sulfur atom Chemical group 0.000 abstract description 12
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 11
- 108010080146 androgen receptors Proteins 0.000 abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 7
- 125000006575 electron-withdrawing group Chemical group 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 102000001307 androgen receptors Human genes 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 312
- 239000000203 mixture Substances 0.000 description 154
- 239000000243 solution Substances 0.000 description 153
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 144
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 128
- 101150041968 CDC13 gene Proteins 0.000 description 95
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 95
- 238000002360 preparation method Methods 0.000 description 83
- 239000003814 drug Substances 0.000 description 82
- 238000005160 1H NMR spectroscopy Methods 0.000 description 80
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 78
- 230000002829 reductive effect Effects 0.000 description 78
- 229940079593 drug Drugs 0.000 description 77
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 74
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 68
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 66
- 235000002639 sodium chloride Nutrition 0.000 description 65
- 239000007787 solid Substances 0.000 description 65
- 238000006243 chemical reaction Methods 0.000 description 58
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 51
- 238000000034 method Methods 0.000 description 49
- 239000011541 reaction mixture Substances 0.000 description 49
- 238000010898 silica gel chromatography Methods 0.000 description 49
- 239000003480 eluent Substances 0.000 description 45
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 42
- 239000000284 extract Substances 0.000 description 42
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 41
- 229910000024 caesium carbonate Inorganic materials 0.000 description 41
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 39
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 39
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 33
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
- 239000012230 colorless oil Substances 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 239000000126 substance Substances 0.000 description 25
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 24
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 238000002347 injection Methods 0.000 description 24
- 239000007924 injection Substances 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
- 239000000546 pharmaceutical excipient Substances 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000000706 filtrate Substances 0.000 description 19
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 18
- 235000019441 ethanol Nutrition 0.000 description 18
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 238000000576 coating method Methods 0.000 description 17
- 229920006395 saturated elastomer Polymers 0.000 description 17
- 230000000694 effects Effects 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
- 239000003405 delayed action preparation Substances 0.000 description 15
- 239000003921 oil Substances 0.000 description 15
- 235000019198 oils Nutrition 0.000 description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 15
- AYQBMZNSJPVADT-UHFFFAOYSA-N 4-bromo-2-chlorobenzonitrile Chemical compound ClC1=CC(Br)=CC=C1C#N AYQBMZNSJPVADT-UHFFFAOYSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 239000003098 androgen Substances 0.000 description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 14
- 229940043279 diisopropylamine Drugs 0.000 description 14
- XLXSAKCOAKORKW-AQJXLSMYSA-N gonadorelin Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)NCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 XLXSAKCOAKORKW-AQJXLSMYSA-N 0.000 description 14
- 239000001257 hydrogen Substances 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- 239000000314 lubricant Substances 0.000 description 14
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 229910052731 fluorine Inorganic materials 0.000 description 13
- 125000001153 fluoro group Chemical group F* 0.000 description 13
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 13
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 13
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 13
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 12
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 12
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 12
- 229920002472 Starch Polymers 0.000 description 12
- 235000019270 ammonium chloride Nutrition 0.000 description 12
- 239000012298 atmosphere Substances 0.000 description 12
- 229920002678 cellulose Polymers 0.000 description 12
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 12
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 12
- 235000010355 mannitol Nutrition 0.000 description 12
- 229920001223 polyethylene glycol Polymers 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- 239000008107 starch Substances 0.000 description 12
- 235000019698 starch Nutrition 0.000 description 12
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- RBRTXKYFMXVIER-UHFFFAOYSA-N 4-iodo-2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC(I)=CC=C1C#N RBRTXKYFMXVIER-UHFFFAOYSA-N 0.000 description 11
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 11
- 206010028980 Neoplasm Diseases 0.000 description 11
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 11
- 239000002202 Polyethylene glycol Substances 0.000 description 11
- 150000001413 amino acids Chemical class 0.000 description 11
- 235000010980 cellulose Nutrition 0.000 description 11
- 239000001913 cellulose Substances 0.000 description 11
- 235000015165 citric acid Nutrition 0.000 description 11
- 239000013078 crystal Substances 0.000 description 11
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 11
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 11
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 11
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 11
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 11
- 239000003381 stabilizer Substances 0.000 description 11
- 238000001356 surgical procedure Methods 0.000 description 11
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 229930006000 Sucrose Natural products 0.000 description 10
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 239000000654 additive Substances 0.000 description 10
- 239000000556 agonist Substances 0.000 description 10
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 10
- 230000032050 esterification Effects 0.000 description 10
- 238000005886 esterification reaction Methods 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
- 229960004793 sucrose Drugs 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 229940024606 amino acid Drugs 0.000 description 9
- 235000001014 amino acid Nutrition 0.000 description 9
- 239000002246 antineoplastic agent Substances 0.000 description 9
- 201000011510 cancer Diseases 0.000 description 9
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 9
- XLXSAKCOAKORKW-UHFFFAOYSA-N gonadorelin Chemical compound C1CCC(C(=O)NCC(N)=O)N1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 XLXSAKCOAKORKW-UHFFFAOYSA-N 0.000 description 9
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| JP2007-299658 | 2007-11-19 | ||
| JP2007299658 | 2007-11-19 | ||
| PCT/JP2008/064500 WO2009020234A2 (en) | 2007-08-07 | 2008-08-06 | Pyrrolidin-2 -one derivatives as androgen receptor modulator |
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| CA2695852A1 CA2695852A1 (en) | 2009-02-12 |
| CA2695852C true CA2695852C (en) | 2017-01-03 |
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| US8268872B2 (en) * | 2008-02-22 | 2012-09-18 | Radius Health, Inc. | Selective androgen receptor modulators |
| MX2010009162A (es) | 2008-02-22 | 2010-12-21 | Radius Health Inc | Moduladores selectivos del receptor de androgeno. |
| AR071069A1 (es) * | 2008-03-26 | 2010-05-26 | Takeda Pharmaceutical | Derivados sustituidos de pirazol y su uso para la prevencion o el tratamiento de cancer |
| EP2531029B1 (en) | 2010-02-04 | 2016-10-19 | Radius Health, Inc. | Selective androgen receptor modulators |
| WO2011143469A1 (en) | 2010-05-12 | 2011-11-17 | Radius Health,Inc | Therapeutic regimens |
| US8642632B2 (en) | 2010-07-02 | 2014-02-04 | Radius Health, Inc. | Selective androgen receptor modulators |
| BR112013007685B1 (pt) | 2010-09-28 | 2021-11-09 | Radius Pharmaceuticals, Inc | Compostos moduladores de receptor andrógeno seletivos, composição farmacêutica compreendendo os referidos compostos, método de identificação de um composto capaz de modular um receptor andrógeno, usos de um composto ou da composição e processo para a preparação de um composto |
| US20150057452A1 (en) * | 2012-04-04 | 2015-02-26 | Catylix, Inc. | Selective androgen receptor modulators |
| CN104768544B (zh) | 2012-08-09 | 2017-06-16 | 迪纳米斯治疗公司 | 包括葡甲胺或其盐的组合物在制备减少或预防甘油三酯水平增加的药物中的应用 |
| JP6338583B2 (ja) * | 2012-09-21 | 2018-06-06 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | Ｃ−ｃ三重結合を有する化合物およびそれらの液晶混合物における使用。 |
| US9421264B2 (en) | 2014-03-28 | 2016-08-23 | Duke University | Method of treating cancer using selective estrogen receptor modulators |
| FI3834824T3 (fi) | 2014-03-28 | 2025-12-05 | Univ Duke | Estrogeenireseptoripositiivisen rintasyövän hoito selektiivisellä estrogeenireseptorin modulaattorilla |
| KR101597327B1 (ko) | 2014-04-24 | 2016-02-24 | 동아에스티 주식회사 | 옥사졸리딘계 화합물 및 이를 포함하는 선택적 안드로겐 수용체 효능제 |
| CN103951688B (zh) * | 2014-05-06 | 2016-04-20 | 成都安斯利生物医药有限公司 | 一种制备3,5-二氟-4-甲基苯硼酸的方法 |
| JP7221699B2 (ja) | 2016-06-22 | 2023-02-14 | エリプセス ファーマ エルティーディー | Ａｒ＋乳癌の治療方法 |
| KR102881465B1 (ko) | 2017-01-05 | 2025-11-04 | 래디어스 파마슈티컬스, 인코포레이티드 | Rad1901-2hcl의 다형 형태 |
| SG11202013177WA (en) | 2018-07-04 | 2021-01-28 | Radius Pharmaceuticals Inc | Polymorphic forms of rad 1901-2hcl |
| EP3908581A1 (en) | 2019-01-11 | 2021-11-17 | Grünenthal GmbH | Substituted pyrrolidine amides iii |
| KR20210127961A (ko) | 2019-02-12 | 2021-10-25 | 래디어스 파마슈티컬스, 인코포레이티드 | 방법 및 화합물 |
| CN110204505B (zh) * | 2019-05-31 | 2023-02-03 | 荆门医药工业技术研究院 | (s)-3-苄氧羰基-4-异丙基-2,5-恶唑烷二酮的制备工艺 |
| US20230012570A1 (en) * | 2019-11-20 | 2023-01-19 | Medshine Discovery Inc. | Bicyclic compound used as selective androgen receptor modulator |
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| DE4141399A1 (de) | 1991-12-16 | 1993-06-17 | Bayer Ag | 4-(substituierte)amino-3-arylpyrrolinon-derivate |
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| US6258833B1 (en) | 1999-12-23 | 2001-07-10 | Icos Corporation | Cyclic AMP-specific phosphodiesterase inhibitors |
| US7026500B2 (en) | 2000-08-24 | 2006-04-11 | University Of Tennessee Research Foundation | Halogenated selective androgen receptor modulators and methods of use thereof |
| JP2002088073A (ja) * | 2000-09-08 | 2002-03-27 | Yamanouchi Pharmaceut Co Ltd | 抗アンドロゲン剤 |
| FR2817472B1 (fr) | 2000-12-06 | 2003-01-03 | Oreal | Composition de teinture d'oxydation a base de 1-(4-aminophenyl)pyrrolidines substituees au moins en position 2 et 3 et procede de teinture de mise en oeuvre |
| PT1463497E (pt) | 2001-12-06 | 2011-12-20 | Gtx Inc | Tratamento do desgaste muscular com moduladores selectivos do receptor de androgénios |
| JP4316232B2 (ja) | 2001-12-28 | 2009-08-19 | 武田薬品工業株式会社 | アンドロゲン受容体拮抗剤 |
| US20050101657A1 (en) * | 2001-12-28 | 2005-05-12 | Takeda Chemical Industries Ltd. | Androgen receptor antagonists |
| US7022870B2 (en) | 2002-06-17 | 2006-04-04 | University Of Tennessee Research Foundation | N-bridged selective androgen receptor modulators and methods of use thereof |
| KR20050044902A (ko) | 2002-08-12 | 2005-05-13 | 다케다 야쿠힌 고교 가부시키가이샤 | 축합 벤젠 유도체 및 용도 |
| GB0402492D0 (en) | 2004-02-04 | 2004-03-10 | Pfizer Ltd | Pharmaceutically active compounds |
| US8519158B2 (en) * | 2004-03-12 | 2013-08-27 | Ligand Pharmaceuticals Incorporated | Androgen receptor modulator compounds and methods |
| EP1747193A1 (en) * | 2004-05-11 | 2007-01-31 | Pfizer Products Incorporated | Benzonitrile derivatives to treat musculoskeletal frailty |
| CN101248069A (zh) | 2004-05-17 | 2008-08-20 | 阿卡蒂亚药品公司 | 雄激素受体调节剂及用其治疗疾病的方法 |
| AU2005251781C1 (en) | 2004-06-07 | 2008-02-21 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and methods of use thereof |
| KR20070112775A (ko) | 2005-01-10 | 2007-11-27 | 아카디아 파마슈티칼스 인코포레이티드 | 선택적인 안드로겐 수용체 조절자로서의 아미노페닐 유도체 |
| TW200724139A (en) * | 2005-05-05 | 2007-07-01 | Warner Lambert Co | Androgen modulators |
| JP5089578B2 (ja) | 2005-05-13 | 2012-12-05 | イーライ リリー アンド カンパニー | 選択的なアンドロゲン受容体調節物質としての置換型ｎ−アリールピロリジン |
| CA2617256C (en) | 2005-08-01 | 2014-07-15 | Takeda Pharmaceutical Company Limited | Cyclic amine compound |
| US20090042857A1 (en) | 2006-02-20 | 2009-02-12 | Masuo Yamaoka | Novel Pharmaceutical |
| MX2009000714A (es) | 2006-07-19 | 2009-07-27 | Osurf | Moduladores de receptor de androgeno selectivos, analogos y derivados de los mismos. |
| CA2658558A1 (en) | 2006-07-26 | 2008-01-31 | Novartis Ag | Inhibitors of undecaprenyl pyrophosphate synthase |
| WO2008066117A1 (en) | 2006-11-30 | 2008-06-05 | Takeda Pharmaceutical Company Limited | Cyclic amine compound |
| EA017429B1 (ru) | 2007-08-07 | 2012-12-28 | Такеда Фармасьютикал Компани Лимитед | Циклические аминные соединения |
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