TWI483725B - 作為選擇性雄激素受體調節劑之新穎雜環衍生物 - Google Patents

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Publication number

TWI483725B

TWI483725B TW094140006A TW94140006A TWI483725B TW I483725 B TWI483725 B TW I483725B TW 094140006 A TW094140006 A TW 094140006A TW 94140006 A TW94140006 A TW 94140006A TW I483725 B TWI483725 B TW I483725B

Authority

TW

Taiwan

Prior art keywords

group

alkyl

phenyl

methyl

hydrogen

Prior art date

2004-11-16

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• 125000000623 heterocyclic group Chemical group 0.000 title claims description 9
• 239000000849 selective androgen receptor modulator Substances 0.000 title description 6
• -1 tert-butyl-dimethyl-decyl Chemical group 0.000 claims description 454
• 150000001875 compounds Chemical class 0.000 claims description 448
• 125000000217 alkyl group Chemical group 0.000 claims description 368
• 239000001257 hydrogen Substances 0.000 claims description 199
• 229910052739 hydrogen Inorganic materials 0.000 claims description 199
• 125000005843 halogen group Chemical group 0.000 claims description 134
• 150000002431 hydrogen Chemical class 0.000 claims description 124
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 69
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 66
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 56
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
• 125000003545 alkoxy group Chemical group 0.000 claims description 47
• 239000000460 chlorine Substances 0.000 claims description 47
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
• 229910052757 nitrogen Inorganic materials 0.000 claims description 44
• 239000000203 mixture Substances 0.000 claims description 43
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 41
• 150000003839 salts Chemical class 0.000 claims description 41
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 36
• 125000001424 substituent group Chemical group 0.000 claims description 34
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 34
• 229910052801 chlorine Inorganic materials 0.000 claims description 31
• 229910052760 oxygen Inorganic materials 0.000 claims description 29
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 28
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 26
• 229910052717 sulfur Inorganic materials 0.000 claims description 24
• 229910052799 carbon Inorganic materials 0.000 claims description 21
• 125000004076 pyridyl group Chemical group 0.000 claims description 17
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 17
• 229910052794 bromium Inorganic materials 0.000 claims description 15
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
• 239000003937 drug carrier Substances 0.000 claims description 14
• 229910052736 halogen Inorganic materials 0.000 claims description 14
• 150000002367 halogens Chemical class 0.000 claims description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
• XOFVFCWODMAWNV-UHFFFAOYSA-N 5-methyl-3-(trifluoromethyl)-1,4-dihydropyrazole-5-carboxylic acid Chemical compound OC(=O)C1(C)CC(C(F)(F)F)=NN1 XOFVFCWODMAWNV-UHFFFAOYSA-N 0.000 claims description 13
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
• 150000001335 aliphatic alkanes Chemical group 0.000 claims description 11
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
• 125000003282 alkyl amino group Chemical group 0.000 claims description 10
• RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims description 10
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
• 125000003342 alkenyl group Chemical group 0.000 claims description 9
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
• 238000006467 substitution reaction Methods 0.000 claims description 5
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• 150000004820 halides Chemical class 0.000 claims description 4
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 239000007983 Tris buffer Substances 0.000 claims description 3
• XOFVFCWODMAWNV-YFKPBYRVSA-N (5s)-5-methyl-3-(trifluoromethyl)-1,4-dihydropyrazole-5-carboxylic acid Chemical compound OC(=O)[C@]1(C)CC(C(F)(F)F)=NN1 XOFVFCWODMAWNV-YFKPBYRVSA-N 0.000 claims description 2
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 3
• 125000005037 alkyl phenyl group Chemical group 0.000 claims 3
• ZNPKAOCQMDJBIK-UHFFFAOYSA-N nitrocyanamide Chemical compound [O-][N+](=O)NC#N ZNPKAOCQMDJBIK-UHFFFAOYSA-N 0.000 claims 2
• HUEGXHVJCBCOAE-UHFFFAOYSA-N 5-ethyl-3-(trifluoromethyl)-1,4-dihydropyrazole-5-carboxylic acid Chemical compound CCC1(C(O)=O)CC(C(F)(F)F)=NN1 HUEGXHVJCBCOAE-UHFFFAOYSA-N 0.000 claims 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 184
• 239000007787 solid Substances 0.000 description 152
• 238000000034 method Methods 0.000 description 87
• 235000019439 ethyl acetate Nutrition 0.000 description 69
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 69
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 50
• 238000006243 chemical reaction Methods 0.000 description 43
• 239000011541 reaction mixture Substances 0.000 description 41
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 35
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 34
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 28
• 239000011734 sodium Substances 0.000 description 28
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 25
• 239000003960 organic solvent Substances 0.000 description 24
• 235000002639 sodium chloride Nutrition 0.000 description 23
• 239000002904 solvent Substances 0.000 description 22
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
• 239000012267 brine Substances 0.000 description 21
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 21
• 239000002585 base Substances 0.000 description 20
• 239000002253 acid Substances 0.000 description 19
• 239000012044 organic layer Substances 0.000 description 19
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
• 125000003118 aryl group Chemical group 0.000 description 18
• 239000012043 crude product Substances 0.000 description 18
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
• 239000000243 solution Substances 0.000 description 17
• 239000003921 oil Substances 0.000 description 16
• 235000019198 oils Nutrition 0.000 description 16
• 125000001072 heteroaryl group Chemical group 0.000 description 15
• 239000003826 tablet Substances 0.000 description 15
• 125000000592 heterocycloalkyl group Chemical group 0.000 description 14
• 238000002360 preparation method Methods 0.000 description 14
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 14
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 12
• 150000001412 amines Chemical group 0.000 description 12
• 102000001307 androgen receptors Human genes 0.000 description 12
• 108010080146 androgen receptors Proteins 0.000 description 12
• 238000004440 column chromatography Methods 0.000 description 12
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
• 235000019441 ethanol Nutrition 0.000 description 11
• 239000000725 suspension Substances 0.000 description 11
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
• 239000002775 capsule Substances 0.000 description 10
• 125000000753 cycloalkyl group Chemical group 0.000 description 10
• 125000005842 heteroatom Chemical group 0.000 description 10
• 239000003981 vehicle Substances 0.000 description 10
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
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• 210000002307 prostate Anatomy 0.000 description 9
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 9
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• 125000004432 carbon atom Chemical group C* 0.000 description 5
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