CA2812699A1

CA2812699A1 - Inhibiteurs du virus de l'hepatite c

Inhibiteurs du virus de l'hepatite c 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)

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/fr

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
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 73
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 72
-1 NS3 Proteins 0.000 description 65
229940093499 ethyl acetate Drugs 0.000 description 64
239000001257 hydrogen Substances 0.000 description 63
235000019439 ethyl acetate Nutrition 0.000 description 62
238000002360 preparation method Methods 0.000 description 59
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 56
238000006243 chemical reaction Methods 0.000 description 55
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 54
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
239000012267 brine Substances 0.000 description 51
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 51
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 48
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
239000005695 Ammonium acetate Substances 0.000 description 42
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
235000019257 ammonium acetate Nutrition 0.000 description 42
229940043376 ammonium acetate Drugs 0.000 description 42
101150041968 CDC13 gene Proteins 0.000 description 40
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 40
239000003921 oil Substances 0.000 description 40
239000012044 organic layer Substances 0.000 description 40
229910052757 nitrogen Inorganic materials 0.000 description 39
235000019198 oils Nutrition 0.000 description 39
238000000746 purification Methods 0.000 description 39
239000000741 silica gel Substances 0.000 description 38
229910002027 silica gel Inorganic materials 0.000 description 38
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
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 30
239000006260 foam Substances 0.000 description 28
230000002829 reductive effect Effects 0.000 description 28
229910052938 sodium sulfate Inorganic materials 0.000 description 28
235000011152 sodium sulphate Nutrition 0.000 description 28
239000013058 crude material Substances 0.000 description 27
238000004007 reversed phase HPLC Methods 0.000 description 27
239000007832 Na2SO4 Substances 0.000 description 26
125000000753 cycloalkyl group Chemical group 0.000 description 26
125000001424 substituent group Chemical group 0.000 description 26
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
229910003827 NRaRb Inorganic materials 0.000 description 25
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
239000003814 drug Substances 0.000 description 23
229910052943 magnesium sulfate Inorganic materials 0.000 description 23
235000019341 magnesium sulphate Nutrition 0.000 description 23
238000003756 stirring Methods 0.000 description 23
125000000623 heterocyclic group Chemical group 0.000 description 22
229940079322 interferon Drugs 0.000 description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 22
239000000047 product Substances 0.000 description 22
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 21
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
125000001072 heteroaryl group Chemical group 0.000 description 18
239000007788 liquid Substances 0.000 description 18
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 17
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
125000002887 hydroxy group Chemical group [H]O* 0.000 description 17
239000010410 layer Substances 0.000 description 17
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 16
101800001554 RNA-directed RNA polymerase Proteins 0.000 description 16
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239000000463 material Substances 0.000 description 16
239000008194 pharmaceutical composition Substances 0.000 description 16
PCRRPOJDJXDSHT-ZETCQYMHSA-N (2s)-2-(methoxycarbonylamino)-2-(oxan-4-yl)acetic acid Chemical compound COC(=O)N[C@H](C(O)=O)C1CCOCC1 PCRRPOJDJXDSHT-ZETCQYMHSA-N 0.000 description 15
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000006196 drop Substances 0.000 description 15
238000004128 high performance liquid chromatography Methods 0.000 description 15
239000012071 phase Substances 0.000 description 15
239000011734 sodium Substances 0.000 description 15
239000000126 substance Substances 0.000 description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
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
239000000706 filtrate Substances 0.000 description 14
229960000329 ribavirin Drugs 0.000 description 14
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
239000000872 buffer Substances 0.000 description 13
229910052799 carbon Inorganic materials 0.000 description 13
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
229920006395 saturated elastomer Polymers 0.000 description 13
239000003643 water by type Substances 0.000 description 13
239000005909 Kieselgur Substances 0.000 description 12
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 12
239000004480 active ingredient Substances 0.000 description 12
238000001816 cooling Methods 0.000 description 12
238000009472 formulation Methods 0.000 description 12
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125000002619 bicyclic group Chemical group 0.000 description 11
125000004432 carbon atom Chemical group C* 0.000 description 11
108010026228 mRNA guanylyltransferase Proteins 0.000 description 11
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239000008096 xylene Substances 0.000 description 11
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 10
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
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150000007513 acids Chemical class 0.000 description 10
150000001345 alkine derivatives Chemical class 0.000 description 10
125000005843 halogen group Chemical group 0.000 description 10
238000002347 injection Methods 0.000 description 10
239000007924 injection Substances 0.000 description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
101000956368 Trittame loki CRISP/Allergen/PR-1 Proteins 0.000 description 9
125000003342 alkenyl group Chemical group 0.000 description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
125000004093 cyano group Chemical group *C#N 0.000 description 9
239000000284 extract Substances 0.000 description 9
125000005842 heteroatom Chemical group 0.000 description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 9
229910052760 oxygen Inorganic materials 0.000 description 9
239000001301 oxygen Chemical group 0.000 description 9
229910052701 rubidium Inorganic materials 0.000 description 9
238000000926 separation method Methods 0.000 description 9
239000011593 sulfur Chemical group 0.000 description 9
239000003826 tablet Substances 0.000 description 9
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
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 8
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 8
239000000543 intermediate Substances 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
125000004433 nitrogen atom Chemical group N* 0.000 description 8
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 8
238000011282 treatment Methods 0.000 description 8
101710179624 Antiviral serine protease Proteins 0.000 description 7
FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 7
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
229910021529 ammonia Inorganic materials 0.000 description 7
150000001721 carbon Chemical group 0.000 description 7
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 7
230000006870 function Effects 0.000 description 7
239000005457 ice water Substances 0.000 description 7
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
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
125000004438 haloalkoxy group Chemical group 0.000 description 6
125000002883 imidazolyl group Chemical group 0.000 description 6
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000007858 starting material Substances 0.000 description 6
DVFXLNFDWATPMW-IWOKLKJTSA-N tert-butyldiphenylsilyl Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)C(C)(C)C)[C@@H](OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OC[C@@H]2[C@H](CC(O2)N2C3=NC=NC(N)=C3N=C2)OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)O)C1 DVFXLNFDWATPMW-IWOKLKJTSA-N 0.000 description 6
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QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 5
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HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
229910021595 Copper(I) iodide Inorganic materials 0.000 description 5
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CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 5
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239000002585 base Substances 0.000 description 5
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