TW200813007A - Substituted pyrrole derivatives - Google Patents

Substituted pyrrole derivatives Download PDF

Info

Publication number: TW200813007A
Authority: TW; Taiwan
Prior art keywords: group; substituted; optionally substituted; cyanophenyl; cyano
Prior art date: 2006-06-13

Application number

TW096121111A

Other languages

English (en)

Chinese (zh)

Inventor

Mitsuhiro Ito

Nobuyuki Matsunaga

Masami Yamada

Takenori Hitaka

Satoshi Yamamoto

Original Assignee

Takeda Pharmaceutical

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2006-06-13

Filing date

2007-06-12

Publication date

2008-03-16

2007-06-12 Application filed by Takeda Pharmaceutical filed Critical Takeda Pharmaceutical

2008-03-16 Publication of TW200813007A publication Critical patent/TW200813007A/zh

Links

150000003233 pyrroles Chemical class 0.000 title abstract description 9
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 86
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 46
125000003396 thiol group Chemical class [H]S* 0.000 claims abstract description 43
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 41
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 37
125000002971 oxazolyl group Chemical group 0.000 claims abstract description 30
125000000335 thiazolyl group Chemical group 0.000 claims abstract description 17
125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 11
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 8
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract 2
-1 (1) thiazolyl Chemical group 0.000 claims description 278
150000001875 compounds Chemical class 0.000 claims description 194
125000000217 alkyl group Chemical group 0.000 claims description 132
150000003839 salts Chemical class 0.000 claims description 94
239000003814 drug Substances 0.000 claims description 85
229940079593 drug Drugs 0.000 claims description 71
238000000034 method Methods 0.000 claims description 61
239000002253 acid Substances 0.000 claims description 60
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 45
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 41
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 36
125000005843 halogen group Chemical group 0.000 claims description 36
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 34
239000000126 substance Substances 0.000 claims description 27
230000001419 dependent effect Effects 0.000 claims description 24
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 22
125000003118 aryl group Chemical group 0.000 claims description 22
150000001412 amines Chemical group 0.000 claims description 20
125000003277 amino group Chemical group 0.000 claims description 20
125000003342 alkenyl group Chemical group 0.000 claims description 19
239000002689 soil Substances 0.000 claims description 18
229940088597 hormone Drugs 0.000 claims description 17
239000005556 hormone Substances 0.000 claims description 17
229940002612 prodrug Drugs 0.000 claims description 16
239000000651 prodrug Substances 0.000 claims description 16
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 15
108010080146 androgen receptors Proteins 0.000 claims description 15
229940044551 receptor antagonist Drugs 0.000 claims description 15
239000002464 receptor antagonist Substances 0.000 claims description 15
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
125000004076 pyridyl group Chemical group 0.000 claims description 13
206010028980 Neoplasm Diseases 0.000 claims description 12
206010060862 Prostate cancer Diseases 0.000 claims description 12
208000000236 Prostatic Neoplasms Diseases 0.000 claims description 12
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 10
201000011510 cancer Diseases 0.000 claims description 10
125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 9
239000007789 gas Substances 0.000 claims description 8
125000001041 indolyl group Chemical group 0.000 claims description 8
150000002923 oximes Chemical class 0.000 claims description 8
125000003831 tetrazolyl group Chemical group 0.000 claims description 8
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 6
241000124008 Mammalia Species 0.000 claims description 6
238000006467 substitution reaction Methods 0.000 claims description 6
229940124597 therapeutic agent Drugs 0.000 claims description 6
102000001307 androgen receptors Human genes 0.000 claims description 5
230000003042 antagnostic effect Effects 0.000 claims description 5
125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 4
LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 4
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
125000003943 azolyl group Chemical group 0.000 claims description 4
125000004802 cyanophenyl group Chemical group 0.000 claims description 4
230000003449 preventive effect Effects 0.000 claims description 4
HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 claims description 3
125000004103 aminoalkyl group Chemical group 0.000 claims description 3
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 3
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000001425 triazolyl group Chemical group 0.000 claims description 3
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 2
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 2
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 2
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
239000005642 Oleic acid Substances 0.000 claims description 2
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 2
240000007594 Oryza sativa Species 0.000 claims description 2
235000007164 Oryza sativa Nutrition 0.000 claims description 2
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
230000002265 prevention Effects 0.000 claims description 2
235000009566 rice Nutrition 0.000 claims description 2
PCYWMDGJYQAMCR-UHFFFAOYSA-N 1h-pyrrole-3-carbonitrile Chemical compound N#CC=1C=CNC=1 PCYWMDGJYQAMCR-UHFFFAOYSA-N 0.000 claims 2
150000001454 anthracenes Chemical class 0.000 claims 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
PNAFRZGWUVQUKH-UHFFFAOYSA-N 1,3-thiazole-4-carbonitrile Chemical compound N#CC1=CSC=N1 PNAFRZGWUVQUKH-UHFFFAOYSA-N 0.000 claims 1
UPUWMQZUXFAUCJ-UHFFFAOYSA-N 2,5-dihydro-1,2-thiazole Chemical compound C1SNC=C1 UPUWMQZUXFAUCJ-UHFFFAOYSA-N 0.000 claims 1
BPMBNLJJRKCCRT-UHFFFAOYSA-N 4-phenylbenzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CC=CC=C1 BPMBNLJJRKCCRT-UHFFFAOYSA-N 0.000 claims 1
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 1
240000008570 Digitaria exilis Species 0.000 claims 1
235000005459 Digitaria exilis Nutrition 0.000 claims 1
229940123502 Hormone receptor antagonist Drugs 0.000 claims 1
235000010575 Pueraria lobata Nutrition 0.000 claims 1
239000004098 Tetracycline Substances 0.000 claims 1
230000003796 beauty Effects 0.000 claims 1
239000003183 carcinogenic agent Substances 0.000 claims 1
230000007717 exclusion Effects 0.000 claims 1
ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 claims 1
239000003689 hormone receptor blocking agent Substances 0.000 claims 1
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims 1
WLBNVSIQCFHAQB-UHFFFAOYSA-N methyl 1h-pyrrole-3-carboxylate Chemical compound COC(=O)C=1C=CNC=1 WLBNVSIQCFHAQB-UHFFFAOYSA-N 0.000 claims 1
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
150000002916 oxazoles Chemical class 0.000 claims 1
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims 1
229960002180 tetracycline Drugs 0.000 claims 1
229930101283 tetracycline Natural products 0.000 claims 1
235000019364 tetracycline Nutrition 0.000 claims 1
150000003536 tetrazoles Chemical class 0.000 claims 1
125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 1
125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
235000013311 vegetables Nutrition 0.000 claims 1
229940123407 Androgen receptor antagonist Drugs 0.000 abstract description 11
125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract description 11
239000003936 androgen receptor antagonist Substances 0.000 abstract description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 361
125000001424 substituent group Chemical group 0.000 description 143
235000019439 ethyl acetate Nutrition 0.000 description 136
239000000203 mixture Substances 0.000 description 131
239000000243 solution Substances 0.000 description 111
238000006243 chemical reaction Methods 0.000 description 94
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 82
238000002360 preparation method Methods 0.000 description 69
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 65
239000011541 reaction mixture Substances 0.000 description 59
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 57
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 57
238000005481 NMR spectroscopy Methods 0.000 description 53
239000000047 product Substances 0.000 description 53
239000013078 crystal Substances 0.000 description 48
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 43
239000002904 solvent Substances 0.000 description 43
239000003795 chemical substances by application Substances 0.000 description 39
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 37
239000002585 base Substances 0.000 description 36
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 35
235000019441 ethanol Nutrition 0.000 description 34
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 30
229920002678 cellulose Polymers 0.000 description 29
239000001913 cellulose Substances 0.000 description 29
235000010980 cellulose Nutrition 0.000 description 29
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 29
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 28
238000010898 silica gel chromatography Methods 0.000 description 28
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
239000012044 organic layer Substances 0.000 description 26
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 25
239000011248 coating agent Substances 0.000 description 25
102000005962 receptors Human genes 0.000 description 25
108020003175 receptors Proteins 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 23
GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 23
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 23
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 21
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000003921 oil Substances 0.000 description 21
235000019198 oils Nutrition 0.000 description 21
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 21
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 20
239000010949 copper Substances 0.000 description 20
239000010410 layer Substances 0.000 description 20
229910052751 metal Inorganic materials 0.000 description 20
239000002184 metal Substances 0.000 description 20
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 19
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 19
230000002411 adverse Effects 0.000 description 18
239000003960 organic solvent Substances 0.000 description 18
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 17
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 description 17
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 16
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 16
238000000576 coating method Methods 0.000 description 16
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 16
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 15
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 15
239000000843 powder Substances 0.000 description 15
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
238000001816 cooling Methods 0.000 description 14
238000001914 filtration Methods 0.000 description 14
229920000642 polymer Polymers 0.000 description 14
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
229910000104 sodium hydride Inorganic materials 0.000 description 14
239000012312 sodium hydride Substances 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
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 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
239000008187 granular material Substances 0.000 description 13
239000000546 pharmaceutical excipient Substances 0.000 description 13
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239000005557 antagonist Substances 0.000 description 12
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RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
229910052786 argon Inorganic materials 0.000 description 11
239000001768 carboxy methyl cellulose Substances 0.000 description 11
229910052801 chlorine Inorganic materials 0.000 description 11
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OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 11
229930195733 hydrocarbon Natural products 0.000 description 11
150000002430 hydrocarbons Chemical class 0.000 description 11
125000000468 ketone group Chemical group 0.000 description 11
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 11
229920006395 saturated elastomer Polymers 0.000 description 11
239000000725 suspension Substances 0.000 description 11
102100032187 Androgen receptor Human genes 0.000 description 10
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 10
239000004305 biphenyl Substances 0.000 description 10
239000012267 brine Substances 0.000 description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
229910052794 bromium Inorganic materials 0.000 description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 10
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GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
229960002066 vinorelbine Drugs 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
235000019166 vitamin D Nutrition 0.000 description 1
239000011710 vitamin D Substances 0.000 description 1
150000003710 vitamin D derivatives Chemical class 0.000 description 1
229940046008 vitamin d Drugs 0.000 description 1
150000003722 vitamin derivatives Chemical class 0.000 description 1
230000001755 vocal effect Effects 0.000 description 1
229960001771 vorozole Drugs 0.000 description 1
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 description 1
238000010792 warming Methods 0.000 description 1
239000004552 water soluble powder Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
229950009268 zinostatin Drugs 0.000 description 1
FYQZGCBXYVWXSP-STTFAQHVSA-N zinostatin stimalamer Chemical compound O1[C@H](C)[C@H](O)[C@H](O)[C@@H](NC)[C@H]1OC1C/2=C/C#C[C@H]3O[C@@]3([C@H]3OC(=O)OC3)C#CC\2=C[C@H]1OC(=O)C1=C(C)C=CC2=C(C)C=C(OC)C=C12 FYQZGCBXYVWXSP-STTFAQHVSA-N 0.000 description 1
229950009233 zinostatin stimalamer Drugs 0.000 description 1
XRASPMIURGNCCH-UHFFFAOYSA-N zoledronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CN1C=CN=C1 XRASPMIURGNCCH-UHFFFAOYSA-N 0.000 description 1
229960004276 zoledronic acid Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

TW096121111A 2006-06-13 2007-06-12 Substituted pyrrole derivatives TW200813007A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP2006163992		2006-06-13

Publications (1)

Publication Number	Publication Date
TW200813007A true TW200813007A (en)	2008-03-16

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ID=38832218

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TW096121111A TW200813007A (en)	2006-06-13	2007-06-12	Substituted pyrrole derivatives

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AR (1)	AR061439A1 (es)
PE (1)	PE20080938A1 (es)
TW (1)	TW200813007A (es)
WO (1)	WO2007145349A2 (es)

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ES2413504T3 (es)	2007-12-21	2013-07-16	Ligand Pharmaceuticals Inc.	Moduladores selectivos del receptor de andrógeno (SARM) y usos de los mismos
CN103102325B (zh) *	2013-01-16	2014-11-12	浙江大学宁波理工学院	一种2-溴代甲基-4-羧酸乙酯噻唑的合成方法
BR112021020864A2 (pt)	2019-04-19	2021-12-14	Ligand Pharm Inc	Formas cristalinas e métodos de produção de formas cristalinas de um composto

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WO2003057669A1 (fr) *	2001-12-28	2003-07-17	Takeda Chemical Industries, Ltd.	Antagonistes du recepteur androgene

2007
- 2007-06-12 WO PCT/JP2007/062194 patent/WO2007145349A2/en not_active Ceased
- 2007-06-12 AR ARP070102559A patent/AR061439A1/es not_active Application Discontinuation
- 2007-06-12 TW TW096121111A patent/TW200813007A/zh unknown
- 2007-06-12 PE PE2007000737A patent/PE20080938A1/es not_active Application Discontinuation

Also Published As

Publication number	Publication date
PE20080938A1 (es)	2008-09-02
WO2007145349A3 (en)	2008-04-03
AR061439A1 (es)	2008-08-27
WO2007145349A2 (en)	2007-12-21

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