JP2009515844A

JP2009515844A - １７アルファ−カルボネート置換基を有する１７ベータ−フルオロメトキシカルボニル−アンドロスタ−４−エン−３−オン化合物

１７アルファ−カルボネート置換基を有する１７ベータ−フルオロメトキシカルボニル−アンドロスタ−４−エン−３−オン化合物 Download PDF

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Publication number: JP2009515844A
Authority: JP; Japan
Prior art keywords: oxy; methyl; hydroxy; difluoro; diene
Prior art date: 2005-11-15
Legal status : Pending

Application number

JP2008539361A

Other languages

English (en)

Japanese (ja)

Other versions

JP2009515844A5 (https=

Inventor

ビガダイク，キース

ニーダム，デボラ

Current Assignee

Glaxo Group Ltd

Original Assignee

Glaxo Group Ltd

Priority date

2005-11-15

Filing date

2006-11-13

Publication date

2009-04-16

2006-11-13 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2009-04-16 Publication of JP2009515844A publication Critical patent/JP2009515844A/ja

2010-01-07 Publication of JP2009515844A5 publication Critical patent/JP2009515844A5/ja

Status Pending legal-status Critical Current

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150000001875 compounds Chemical class 0.000 claims abstract description 163
239000012453 solvate Substances 0.000 claims abstract description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 26
125000000217 alkyl group Chemical group 0.000 claims abstract description 16
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
239000001257 hydrogen Substances 0.000 claims abstract description 14
238000011282 treatment Methods 0.000 claims abstract description 14
238000002360 preparation method Methods 0.000 claims abstract description 12
239000003814 drug Substances 0.000 claims abstract description 11
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
150000002431 hydrogen Chemical class 0.000 claims abstract description 7
206010027654 Allergic conditions Diseases 0.000 claims abstract description 6
150000001602 bicycloalkyls Chemical group 0.000 claims abstract description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 6
238000004519 manufacturing process Methods 0.000 claims abstract description 4
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 3
206010061218 Inflammation Diseases 0.000 claims abstract description 3
229910052736 halogen Inorganic materials 0.000 claims abstract description 3
150000002367 halogens Chemical class 0.000 claims abstract description 3
230000004054 inflammatory process Effects 0.000 claims abstract description 3
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 3
-1 1-ethyl-2-methylpropyl Chemical group 0.000 claims description 157
238000000034 method Methods 0.000 claims description 69
239000000203 mixture Substances 0.000 claims description 49
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 39
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 31
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 30
ZQCAOHVYAHPGEW-SCZYCMLPSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydro-3h-cyclopenta[a]phenanthrene-17-carboxylic acid Chemical compound C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)C(O)=O)[C@@H]4[C@@H]3CCC2=C1 ZQCAOHVYAHPGEW-SCZYCMLPSA-N 0.000 claims description 25
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 20
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 15
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238000009472 formulation Methods 0.000 claims description 10
239000000443 aerosol Substances 0.000 claims description 9
BOJKULTULYSRAS-OTESTREVSA-N Andrographolide Chemical compound C([C@H]1[C@]2(C)CC[C@@H](O)[C@]([C@H]2CCC1=C)(CO)C)\C=C1/[C@H](O)COC1=O BOJKULTULYSRAS-OTESTREVSA-N 0.000 claims description 8
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 8
230000003110 anti-inflammatory effect Effects 0.000 claims description 7
125000003113 cycloheptyloxy group Chemical group C1(CCCCCC1)O* 0.000 claims description 7
125000004410 cyclooctyloxy group Chemical group C1(CCCCCCC1)O* 0.000 claims description 7
241001465754 Metazoa Species 0.000 claims description 5
150000008064 anhydrides Chemical class 0.000 claims description 5
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 5
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239000003085 diluting agent Substances 0.000 claims description 3
NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 3
150000001261 hydroxy acids Chemical class 0.000 claims description 3
239000003380 propellant Substances 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
239000000969 carrier Substances 0.000 claims description 2
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125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 104
239000000126 substance Substances 0.000 abstract 1
230000014759 maintenance of location Effects 0.000 description 89
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 88
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
239000000243 solution Substances 0.000 description 49
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238000006243 chemical reaction Methods 0.000 description 35
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239000002244 precipitate Substances 0.000 description 17
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