JP2010515760A5 - - Google Patents
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- JP2010515760A5 JP2010515760A5 JP2009545720A JP2009545720A JP2010515760A5 JP 2010515760 A5 JP2010515760 A5 JP 2010515760A5 JP 2009545720 A JP2009545720 A JP 2009545720A JP 2009545720 A JP2009545720 A JP 2009545720A JP 2010515760 A5 JP2010515760 A5 JP 2010515760A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- aryl
- compound according
- alkenyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims description 112
- 150000001875 compounds Chemical class 0.000 claims description 105
- -1 NH 2 Chemical group 0.000 claims description 72
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 37
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 125000003342 alkenyl group Chemical group 0.000 claims description 26
- 125000000304 alkynyl group Chemical group 0.000 claims description 24
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000003107 substituted aryl group Chemical group 0.000 claims description 22
- 229940002612 prodrug Drugs 0.000 claims description 21
- 239000000651 prodrug Substances 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 241001465754 Metazoa Species 0.000 claims description 16
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000002252 acyl group Chemical group 0.000 claims description 14
- 125000000539 amino acid group Chemical group 0.000 claims description 14
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 239000001177 diphosphate Substances 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 239000001226 triphosphate Substances 0.000 claims description 10
- 102000006992 Interferon-alpha Human genes 0.000 claims description 9
- 108010047761 Interferon-alpha Proteins 0.000 claims description 9
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 8
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 8
- 208000036142 Viral infection Diseases 0.000 claims description 8
- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000002264 triphosphate group Chemical group [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 claims description 8
- 230000009385 viral infection Effects 0.000 claims description 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 6
- 150000001413 amino acids Chemical class 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 235000011180 diphosphates Nutrition 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 6
- 229960000329 ribavirin Drugs 0.000 claims description 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 6
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 229940124683 HCV polymerase inhibitor Drugs 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 239000002246 antineoplastic agent Substances 0.000 claims description 4
- 239000003443 antiviral agent Substances 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- ISQVBYGGNVVVHB-UHFFFAOYSA-N cyclopentylmethanol Chemical compound OCC1CCCC1 ISQVBYGGNVVVHB-UHFFFAOYSA-N 0.000 claims description 3
- 150000004712 monophosphates Chemical group 0.000 claims description 3
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- OSBKZZCHLHZCDB-PBXRRBTRSA-N (2r,3r,4r)-2,3,4,5-tetrahydroxy-2-methylpentanal Chemical compound O=C[C@@](O)(C)[C@H](O)[C@H](O)CO OSBKZZCHLHZCDB-PBXRRBTRSA-N 0.000 claims description 2
- KDKMTIRSYIHSTB-MROZADKFSA-N (2r,3r,4r)-2,3,4,5-tetrahydroxypentanethial Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C=S KDKMTIRSYIHSTB-MROZADKFSA-N 0.000 claims description 2
- NJYXSKVOTDPOAT-LMVFSUKVSA-N (2r,3r,4r)-2-fluoro-3,4,5-trihydroxypentanal Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](F)C=O NJYXSKVOTDPOAT-LMVFSUKVSA-N 0.000 claims description 2
- SQXRWAVEVYDDBF-LMVFSUKVSA-N (2r,3r,4r)-2-fluoro-3,4,5-trihydroxypentanethial Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](F)C=S SQXRWAVEVYDDBF-LMVFSUKVSA-N 0.000 claims description 2
- NJYXSKVOTDPOAT-WDCZJNDASA-N (2s,3r,4r)-2-fluoro-3,4,5-trihydroxypentanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](F)C=O NJYXSKVOTDPOAT-WDCZJNDASA-N 0.000 claims description 2
- SQXRWAVEVYDDBF-WDCZJNDASA-N (2s,3r,4r)-2-fluoro-3,4,5-trihydroxypentanethial Chemical compound OC[C@@H](O)[C@@H](O)[C@H](F)C=S SQXRWAVEVYDDBF-WDCZJNDASA-N 0.000 claims description 2
- ANFWGLPWDSXJEH-CRCLSJGQSA-N (3s,4r)-3,4,5-trihydroxypentanethial Chemical compound OC[C@@H](O)[C@@H](O)CC=S ANFWGLPWDSXJEH-CRCLSJGQSA-N 0.000 claims description 2
- JBFNVLCLNHQXCH-CRCLSJGQSA-N (3s,4r)-3-fluoro-4,5-dihydroxypentanethial Chemical compound OC[C@@H](O)[C@@H](F)CC=S JBFNVLCLNHQXCH-CRCLSJGQSA-N 0.000 claims description 2
- LFRDGHVRPSURMV-YFKPBYRVSA-N (4s)-4,5-dihydroxypentanal Chemical compound OC[C@@H](O)CCC=O LFRDGHVRPSURMV-YFKPBYRVSA-N 0.000 claims description 2
- XFBDCPQESJYXPC-YFKPBYRVSA-N (4s)-4,5-dihydroxypentanethial Chemical compound OC[C@@H](O)CCC=S XFBDCPQESJYXPC-YFKPBYRVSA-N 0.000 claims description 2
- LPXOUBDTZSHIOQ-UHFFFAOYSA-N 1,2,4-triazine-5-carbonitrile Chemical compound N#CC1=CN=NC=N1 LPXOUBDTZSHIOQ-UHFFFAOYSA-N 0.000 claims description 2
- IJIHMDVMMUTJEJ-UHFFFAOYSA-N 1,2,4-triazine-5-carboxamide Chemical compound NC(=O)C1=CN=NC=N1 IJIHMDVMMUTJEJ-UHFFFAOYSA-N 0.000 claims description 2
- GERSIKCSWYDFSJ-UHFFFAOYSA-N 1,2,4-triazine-5-carboxylic acid Chemical compound OC(=O)C1=CN=NC=N1 GERSIKCSWYDFSJ-UHFFFAOYSA-N 0.000 claims description 2
- IWUCXVSUMQZMFG-RGDLXGNYSA-N 1-[(2s,3s,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide Chemical compound N1=C(C(=O)N)N=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 IWUCXVSUMQZMFG-RGDLXGNYSA-N 0.000 claims description 2
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical compound O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 claims description 2
- UADBLZFWTJHOJC-UHFFFAOYSA-N 2-(hydroxymethyl)cyclopentan-1-ol Chemical compound OCC1CCCC1O UADBLZFWTJHOJC-UHFFFAOYSA-N 0.000 claims description 2
- VQKBTEBRZHBIGE-BYPYZUCNSA-N 2-[(1s)-1,2-dihydroxyethyl]sulfanylacetaldehyde Chemical compound OC[C@@H](O)SCC=O VQKBTEBRZHBIGE-BYPYZUCNSA-N 0.000 claims description 2
- ASJSAQIRZKANQN-CRCLSJGQSA-N 2-deoxy-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)CC=O ASJSAQIRZKANQN-CRCLSJGQSA-N 0.000 claims description 2
- NGWKEVMCTIVMBA-UHFFFAOYSA-N 2-fluoro-4-(hydroxymethyl)pyrrolidin-3-ol Chemical compound OCC1CNC(F)C1O NGWKEVMCTIVMBA-UHFFFAOYSA-N 0.000 claims description 2
- DITIGNGDSVRJFX-UHFFFAOYSA-N 3-(hydroxymethyl)-4-methylidenecyclopentane-1,2-diol Chemical compound OCC1C(O)C(O)CC1=C DITIGNGDSVRJFX-UHFFFAOYSA-N 0.000 claims description 2
- DWROYQTVCUQGJR-UHFFFAOYSA-N 3-(hydroxymethyl)cyclopent-3-ene-1,2-diol Chemical compound OCC1=CCC(O)C1O DWROYQTVCUQGJR-UHFFFAOYSA-N 0.000 claims description 2
- BSQXZHMREYHKOM-UHFFFAOYSA-N 4-(hydroxymethyl)pyrrolidin-3-ol Chemical compound OCC1CNCC1O BSQXZHMREYHKOM-UHFFFAOYSA-N 0.000 claims description 2
- UKDQIWLEEJYIDQ-UHFFFAOYSA-N 4-(hydroxymethyl)pyrrolidine-2,3-diol Chemical compound OCC1CNC(O)C1O UKDQIWLEEJYIDQ-UHFFFAOYSA-N 0.000 claims description 2
- AAJXJLYUWKMQNO-UHFFFAOYSA-N 4-chloro-2-(1,2-oxazol-5-yl)phenol Chemical compound OC1=CC=C(Cl)C=C1C1=CC=NO1 AAJXJLYUWKMQNO-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 claims description 2
- 102000016928 DNA-directed DNA polymerase Human genes 0.000 claims description 2
- 108010014303 DNA-directed DNA polymerase Proteins 0.000 claims description 2
- 241001115402 Ebolavirus Species 0.000 claims description 2
- 241001466953 Echovirus Species 0.000 claims description 2
- 241000709661 Enterovirus Species 0.000 claims description 2
- 241000991587 Enterovirus C Species 0.000 claims description 2
- 208000005176 Hepatitis C Diseases 0.000 claims description 2
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 2
- 229940121740 Inosine monophosphate dehydrogenase inhibitor Drugs 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 101710118046 RNA-directed RNA polymerase Proteins 0.000 claims description 2
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims description 2
- 229940122055 Serine protease inhibitor Drugs 0.000 claims description 2
- 101710102218 Serine protease inhibitor Proteins 0.000 claims description 2
- 108010078233 Thymalfasin Proteins 0.000 claims description 2
- 102400000800 Thymosin alpha-1 Human genes 0.000 claims description 2
- 241000700647 Variola virus Species 0.000 claims description 2
- 241000700605 Viruses Species 0.000 claims description 2
- 241000710886 West Nile virus Species 0.000 claims description 2
- GAADRFVRUBFCML-UHFFFAOYSA-N [2-(hydroxymethyl)cyclobutyl]methanol Chemical compound OCC1CCC1CO GAADRFVRUBFCML-UHFFFAOYSA-N 0.000 claims description 2
- WUMYBFXWUJTWTB-UHFFFAOYSA-N [hydroxy(methoxy)phosphoryl] phosphono hydrogen phosphate Chemical compound COP(O)(=O)OP(O)(=O)OP(O)(O)=O WUMYBFXWUJTWTB-UHFFFAOYSA-N 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 claims description 2
- 230000001093 anti-cancer Effects 0.000 claims description 2
- 230000000340 anti-metabolite Effects 0.000 claims description 2
- 229940100197 antimetabolite Drugs 0.000 claims description 2
- 239000002256 antimetabolite Substances 0.000 claims description 2
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- LMYOLOWXQDLHKQ-UHFFFAOYSA-N cyclopent-2-en-1-ylmethanol Chemical compound OCC1CCC=C1 LMYOLOWXQDLHKQ-UHFFFAOYSA-N 0.000 claims description 2
- RGAPPBGFFPGONM-CRCLSJGQSA-N diazonio-[(2s,3s)-1,2-dihydroxy-5-sulfanylidenepentan-3-yl]azanide Chemical compound OC[C@@H](O)[C@H](CC=S)N=[N+]=[N-] RGAPPBGFFPGONM-CRCLSJGQSA-N 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 208000002672 hepatitis B Diseases 0.000 claims description 2
- 229940125697 hormonal agent Drugs 0.000 claims description 2
- 238000000338 in vitro Methods 0.000 claims description 2
- 238000001727 in vivo Methods 0.000 claims description 2
- 239000002348 inosinate dehydrogenase inhibitor Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- DZONTPIFZFRSGP-UHFFFAOYSA-N methyl triazine-5-carboxylate Chemical compound COC(=O)C1=CN=NN=C1 DZONTPIFZFRSGP-UHFFFAOYSA-N 0.000 claims description 2
- 229930014626 natural product Natural products 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000002777 nucleoside Substances 0.000 claims description 2
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- QOTUIIJRVXKSJU-UHFFFAOYSA-N pyrrolidin-3-ylmethanol Chemical compound OCC1CCNC1 QOTUIIJRVXKSJU-UHFFFAOYSA-N 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000003001 serine protease inhibitor Substances 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- NHKZSTHOYNWEEZ-AFCXAGJDSA-N taribavirin Chemical compound N1=C(C(=N)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NHKZSTHOYNWEEZ-AFCXAGJDSA-N 0.000 claims description 2
- 229950006081 taribavirin Drugs 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 2
- NZVYCXVTEHPMHE-ZSUJOUNUSA-N thymalfasin Chemical compound CC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O NZVYCXVTEHPMHE-ZSUJOUNUSA-N 0.000 claims description 2
- 229960004231 thymalfasin Drugs 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 230000003612 virological effect Effects 0.000 claims description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 5
- 235000011178 triphosphate Nutrition 0.000 claims 5
- MJMJUKHABPJQGX-CRCLSJGQSA-N (3s,4r)-3-fluoro-4,5-dihydroxypentanal Chemical compound OC[C@@H](O)[C@@H](F)CC=O MJMJUKHABPJQGX-CRCLSJGQSA-N 0.000 claims 1
- OIEIKVCEXBMETK-BYPYZUCNSA-N 2-[(1s)-1,2-dihydroxyethoxy]acetaldehyde Chemical compound OC[C@@H](O)OCC=O OIEIKVCEXBMETK-BYPYZUCNSA-N 0.000 claims 1
- WQSIEHZPHQVPFS-UHFFFAOYSA-N 3-fluoro-4-(hydroxymethyl)pyrrolidin-2-ol Chemical compound OCC1CNC(O)C1F WQSIEHZPHQVPFS-UHFFFAOYSA-N 0.000 claims 1
- 102000004163 DNA-directed RNA polymerases Human genes 0.000 claims 1
- 108090000626 DNA-directed RNA polymerases Proteins 0.000 claims 1
- 241000701076 Macacine alphaherpesvirus 1 Species 0.000 claims 1
- 230000001548 androgenic effect Effects 0.000 claims 1
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 1
- 238000000034 method Methods 0.000 description 14
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 8
- 0 CCCC(C(CC)(CC1)N)=C=CC(CO*C)C1O Chemical compound CCCC(C(CC)(CC1)N)=C=CC(CO*C)C1O 0.000 description 2
- BPZTVHFVZNQDRE-HCWXCVPCSA-N C[C@@H]1S[C@H](CO)C[C@H]1O Chemical compound C[C@@H]1S[C@H](CO)C[C@H]1O BPZTVHFVZNQDRE-HCWXCVPCSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- SZYJWAORZUSFHW-NTSWFWBYSA-N C=C1S[C@H](CO)C[C@@]1(C(F)(F)F)O Chemical compound C=C1S[C@H](CO)C[C@@]1(C(F)(F)F)O SZYJWAORZUSFHW-NTSWFWBYSA-N 0.000 description 1
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- NBIAJCFWHPLRMX-BGPJRJDNSA-N C[C@@H]([C@@H]1O)S[C@H](CO)[C@H]1O Chemical compound C[C@@H]([C@@H]1O)S[C@H](CO)[C@H]1O NBIAJCFWHPLRMX-BGPJRJDNSA-N 0.000 description 1
- AOOQTVGJBDRQBU-WDSKDSINSA-N C[C@@H]1S[C@H](CO)CC1 Chemical compound C[C@@H]1S[C@H](CO)CC1 AOOQTVGJBDRQBU-WDSKDSINSA-N 0.000 description 1
- AHYCTNVIMLVRSL-UHFFFAOYSA-N OCC1CC(O)N(F)C1 Chemical compound OCC1CC(O)N(F)C1 AHYCTNVIMLVRSL-UHFFFAOYSA-N 0.000 description 1
- USYKCURAQZSEQC-MOJAZDJTSA-N OC[C@H]([C@H]1O)S[C@@H](C2)[C@]12F Chemical compound OC[C@H]([C@H]1O)S[C@@H](C2)[C@]12F USYKCURAQZSEQC-MOJAZDJTSA-N 0.000 description 1
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2008
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- 2008-01-11 DK DK08727625.9T patent/DK2114980T3/da active
- 2008-01-11 NZ NZ578556A patent/NZ578556A/en not_active IP Right Cessation
- 2008-01-11 MX MX2009007333A patent/MX2009007333A/es active IP Right Grant
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- 2008-01-11 SI SI200830771T patent/SI2114980T1/sl unknown
- 2008-01-11 JP JP2009545720A patent/JP2010515760A/ja active Pending
- 2008-01-11 AU AU2008206406A patent/AU2008206406A1/en not_active Abandoned
- 2008-01-11 EP EP12168831A patent/EP2535345A1/en not_active Withdrawn
- 2008-01-11 NZ NZ598927A patent/NZ598927A/xx not_active IP Right Cessation
- 2008-01-11 CN CNA2008800038586A patent/CN101611046A/zh active Pending
- 2008-01-11 US US12/522,892 patent/US8440813B2/en active Active
- 2008-01-11 PT PT08727625T patent/PT2114980E/pt unknown
- 2008-01-11 HR HRP20120758AT patent/HRP20120758T1/hr unknown
- 2008-01-11 PL PL08727625T patent/PL2114980T3/pl unknown
- 2008-01-11 EP EP08727625A patent/EP2114980B1/en not_active Not-in-force
- 2008-01-11 ES ES08727625T patent/ES2390188T3/es active Active
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