CA2812699A1

CA2812699A1 - Hepatitis c virus inhibitors

Hepatitis c virus inhibitors Download PDF

Info

Publication number: CA2812699A1
Authority: CA; Canada
Prior art keywords: mmol; anal; calcd; found; cond
Prior art date: 2010-09-24
Legal status : Abandoned

Application number

CA2812699A

Other languages

English (en)

French (fr)

Inventor

Makonen Belema

Piyasena Hewawasam

Current Assignee

Bristol Myers Squibb Co

Original Assignee

Bristol Myers Squibb Co

Priority date

2010-09-24

Filing date

2010-09-24

Publication date

2012-03-29

2010-09-24 Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co

2012-03-29 Publication of CA2812699A1 publication Critical patent/CA2812699A1/en

Status Abandoned legal-status Critical Current

Links

241000711549 Hepacivirus C Species 0.000 title abstract description 56
239000003112 inhibitor Substances 0.000 title description 37
239000000203 mixture Substances 0.000 claims abstract description 151
150000001875 compounds Chemical class 0.000 claims abstract description 132
238000000034 method Methods 0.000 claims abstract description 110
150000003839 salts Chemical class 0.000 claims description 82
239000003937 drug carrier Substances 0.000 claims description 9
208000015181 infectious disease Diseases 0.000 claims description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 13
101800001014 Non-structural protein 5A Proteins 0.000 abstract description 10
201000010099 disease Diseases 0.000 abstract description 8
230000002401 inhibitory effect Effects 0.000 abstract description 3
239000003443 antiviral agent Substances 0.000 abstract 1
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 333
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 304
229910001868 water Inorganic materials 0.000 description 291
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 202
238000005160 1H NMR spectroscopy Methods 0.000 description 201
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 189
239000002904 solvent Substances 0.000 description 187
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 186
239000000243 solution Substances 0.000 description 183
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 178
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 158
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 119
229910052739 hydrogen Inorganic materials 0.000 description 106
239000011541 reaction mixture Substances 0.000 description 100
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 95
239000007787 solid Substances 0.000 description 94
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 84
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 84
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 82
125000000217 alkyl group Chemical group 0.000 description 78
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-1 NS3 Proteins 0.000 description 65
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238000006243 chemical reaction Methods 0.000 description 55
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239000012267 brine Substances 0.000 description 51
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125000003118 aryl group Chemical group 0.000 description 46
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 45
239000002253 acid Substances 0.000 description 45
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 42
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101150041968 CDC13 gene Proteins 0.000 description 40
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239000012044 organic layer Substances 0.000 description 40
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238000003818 flash chromatography Methods 0.000 description 36
230000000840 anti-viral effect Effects 0.000 description 35
150000002431 hydrogen Chemical group 0.000 description 31
239000012074 organic phase Substances 0.000 description 31
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239000006260 foam Substances 0.000 description 28
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238000004007 reversed phase HPLC Methods 0.000 description 27
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125000000753 cycloalkyl group Chemical group 0.000 description 26
125000001424 substituent group Chemical group 0.000 description 26
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
125000003710 aryl alkyl group Chemical group 0.000 description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 description 24
238000004458 analytical method Methods 0.000 description 23
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238000003756 stirring Methods 0.000 description 23
125000000623 heterocyclic group Chemical group 0.000 description 22
229940079322 interferon Drugs 0.000 description 22
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239000000047 product Substances 0.000 description 22
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239000007821 HATU Substances 0.000 description 21
239000000725 suspension Substances 0.000 description 21
CEFVHPDFGLDQKU-YFKPBYRVSA-N (2s)-2-(methoxycarbonylamino)-3-methylbutanoic acid Chemical compound COC(=O)N[C@@H](C(C)C)C(O)=O CEFVHPDFGLDQKU-YFKPBYRVSA-N 0.000 description 20
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 20
108010050904 Interferons Proteins 0.000 description 20
102000014150 Interferons Human genes 0.000 description 20
239000008346 aqueous phase Substances 0.000 description 20
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 20
150000002148 esters Chemical class 0.000 description 20
229910052736 halogen Inorganic materials 0.000 description 20
150000002367 halogens Chemical class 0.000 description 20
230000014759 maintenance of location Effects 0.000 description 20
238000002953 preparative HPLC Methods 0.000 description 20
239000000523 sample Substances 0.000 description 20
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 19
125000001188 haloalkyl group Chemical group 0.000 description 19
235000017557 sodium bicarbonate Nutrition 0.000 description 19
229910000030 sodium bicarbonate Inorganic materials 0.000 description 19
229910052717 sulfur Chemical group 0.000 description 19
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 18
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
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230000015572 biosynthetic process Effects 0.000 description 17
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 17
238000010828 elution Methods 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
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239000010410 layer Substances 0.000 description 17
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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 description 14
125000003545 alkoxy group Chemical group 0.000 description 14
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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 description 14
238000003786 synthesis reaction Methods 0.000 description 14
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
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230000000694 effects Effects 0.000 description 13
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 13
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GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
229960000549 4-dimethylaminophenol Drugs 0.000 description 8
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239000000543 intermediate Substances 0.000 description 8
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NXFFJDQHYLNEJK-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)C)=CC(F)=CC=2C=2CCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 NXFFJDQHYLNEJK-UHFFFAOYSA-N 0.000 description 6
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