DK2410844T3 - Inhibitors of hepatitis C virus replication - Google Patents
Inhibitors of hepatitis C virus replication Download PDFInfo
- Publication number
- DK2410844T3 DK2410844T3 DK10756840.4T DK10756840T DK2410844T3 DK 2410844 T3 DK2410844 T3 DK 2410844T3 DK 10756840 T DK10756840 T DK 10756840T DK 2410844 T3 DK2410844 T3 DK 2410844T3
- Authority
- DK
- Denmark
- Prior art keywords
- group
- alkyl
- independently selected
- methyl
- hydrogen
- Prior art date
Links
- 241000711549 Hepacivirus C Species 0.000 title claims description 106
- 239000003112 inhibitor Substances 0.000 title claims description 23
- 230000029812 viral genome replication Effects 0.000 title claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 151
- 229910052739 hydrogen Inorganic materials 0.000 claims description 71
- 239000001257 hydrogen Substances 0.000 claims description 71
- -1 -OR3a Chemical group 0.000 claims description 62
- 229910052757 nitrogen Inorganic materials 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 125000001424 substituent group Chemical group 0.000 claims description 56
- 150000002431 hydrogen Chemical class 0.000 claims description 52
- 125000005842 heteroatom Chemical group 0.000 claims description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 39
- 150000002367 halogens Chemical class 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 36
- 229910052717 sulfur Inorganic materials 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 229910052760 oxygen Inorganic materials 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 17
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 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 15
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 15
- 125000003386 piperidinyl group Chemical group 0.000 claims description 15
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 15
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 14
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- 125000004122 cyclic group Chemical group 0.000 claims description 10
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- 125000002619 bicyclic group Chemical group 0.000 claims description 8
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- HPZMZHFCAWVHHF-BCRBLDSWSA-N (2s)-1-(2-phenylacetyl)-n-[8-[[(2s)-1-(2-phenylacetyl)pyrrolidine-2-carbonyl]amino]-6,11-dihydro-5h-benzo[a]carbazol-3-yl]pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CCC1)C(=O)NC=1C=C2CCC=3C4=CC(NC(=O)[C@H]5N(CCC5)C(=O)CC=5C=CC=CC=5)=CC=C4NC=3C2=CC=1)C(=O)CC1=CC=CC=C1 HPZMZHFCAWVHHF-BCRBLDSWSA-N 0.000 claims 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 claims 1
- SLVYYZMCQYMPCI-ZGTCLIOFSA-N 1-[(2r)-2-(dimethylamino)-2-phenylacetyl]pyrrolidine-2-carboxamide Chemical compound O=C([C@H](N(C)C)C=1C=CC=CC=1)N1CCCC1C(N)=O SLVYYZMCQYMPCI-ZGTCLIOFSA-N 0.000 claims 1
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
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- 230000002401 inhibitory effect Effects 0.000 description 20
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 15
- 229910001868 water Inorganic materials 0.000 description 15
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- 229940124597 therapeutic agent Drugs 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 230000005764 inhibitory process Effects 0.000 description 12
- 230000010076 replication Effects 0.000 description 12
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- 208000024891 symptom Diseases 0.000 description 11
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
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- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
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- 229960004231 thymalfasin Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- JKNHZOAONLKYQL-UHFFFAOYSA-K tribromoindigane Chemical compound Br[In](Br)Br JKNHZOAONLKYQL-UHFFFAOYSA-K 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 229950002810 valopicitabine Drugs 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
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Classifications
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- 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
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- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
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- Nitrogen Condensed Heterocyclic Rings (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16395809P | 2009-03-27 | 2009-03-27 | |
| US24731809P | 2009-09-30 | 2009-09-30 | |
| PCT/US2010/028653 WO2010111483A1 (en) | 2009-03-27 | 2010-03-25 | Inhibitors of hepatitis c virus replication |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2410844T3 true DK2410844T3 (en) | 2016-07-04 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK10756840.4T DK2410844T3 (en) | 2009-03-27 | 2010-03-25 | Inhibitors of hepatitis C virus replication |
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