NZ572367A

NZ572367A - Fused cyclic compounds as integrase inhibitors

Fused cyclic compounds as integrase inhibitors

Info

Publication number: NZ572367A
Authority: NZ; New Zealand
Prior art keywords: compound; alkyl; nmr; ppm; optionally substituted
Prior art date: 2006-05-16

Application number

NZ572367A

Other languages

English (en)

Inventor

Zhenhong R Cai

Salman Y Jabri

Haolun Jin

Rachael A Lansdown

Samuel E Metobo

Michael L Mish

Richard Pastor

Original Assignee

Gilead Sciences Inc

Priority date

2006-05-16

Filing date

2007-05-16

Publication date

2011-09-30

2007-05-16 Application filed by Gilead Sciences Inc filed Critical Gilead Sciences Inc

2011-09-30 Publication of NZ572367A publication Critical patent/NZ572367A/en

Links

239000002850 integrase inhibitor Substances 0.000 title description 5
229940124524 integrase inhibitor Drugs 0.000 title description 5
150000001923 cyclic compounds Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 392
239000003814 drug Substances 0.000 claims abstract description 28
208000030507 AIDS Diseases 0.000 claims abstract description 20
241000725303 Human immunodeficiency virus Species 0.000 claims abstract description 16
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
238000004519 manufacturing process Methods 0.000 claims abstract description 8
208000024891 symptom Diseases 0.000 claims abstract description 7
230000035755 proliferation Effects 0.000 claims abstract description 5
-1 dimethylamino, diethylamino Chemical group 0.000 claims description 359
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 118
239000000203 mixture Substances 0.000 claims description 102
150000003839 salts Chemical class 0.000 claims description 96
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
239000003795 chemical substances by application Substances 0.000 claims description 41
125000000217 alkyl group Chemical group 0.000 claims description 39
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 35
125000005843 halogen group Chemical group 0.000 claims description 33
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 31
238000011282 treatment Methods 0.000 claims description 30
125000004093 cyano group Chemical group *C#N 0.000 claims description 28
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
229910052794 bromium Inorganic materials 0.000 claims description 24
125000004076 pyridyl group Chemical group 0.000 claims description 24
229910052740 iodine Inorganic materials 0.000 claims description 23
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 23
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
125000002947 alkylene group Chemical group 0.000 claims description 16
125000001153 fluoro group Chemical group F* 0.000 claims description 16
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 15
229910052799 carbon Inorganic materials 0.000 claims description 15
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 14
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 13
108010002459 HIV Integrase Proteins 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 13
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
102100034343 Integrase Human genes 0.000 claims description 12
230000000840 anti-viral effect Effects 0.000 claims description 11
108010061833 Integrases Proteins 0.000 claims description 10
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
230000002401 inhibitory effect Effects 0.000 claims description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 8
230000005764 inhibitory process Effects 0.000 claims description 8
239000000546 pharmaceutical excipient Substances 0.000 claims description 8
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 7
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 7
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 7
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 7
239000002955 immunomodulating agent Substances 0.000 claims description 7
229940121354 immunomodulator Drugs 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
125000005960 1,4-diazepanyl group Chemical group 0.000 claims description 6
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
229960005475 antiinfective agent Drugs 0.000 claims description 6
239000004599 antimicrobial Substances 0.000 claims description 6
201000010099 disease Diseases 0.000 claims description 6
230000002584 immunomodulator Effects 0.000 claims description 6
KOAMXHRRVFDWRQ-UHFFFAOYSA-N 4,4-dimethyl-5h-1,3-oxazole Chemical compound CC1(C)COC=N1 KOAMXHRRVFDWRQ-UHFFFAOYSA-N 0.000 claims description 5
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
125000001589 carboacyl group Chemical group 0.000 claims description 4
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 3
FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 3
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
208000035475 disorder Diseases 0.000 claims description 3
238000002560 therapeutic procedure Methods 0.000 claims description 3
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
ZMSIFDIKIXVLDF-UHFFFAOYSA-N 2-methyl-1,3,4-oxadiazole Chemical compound CC1=NN=CO1 ZMSIFDIKIXVLDF-UHFFFAOYSA-N 0.000 claims description 2
229940122440 HIV protease inhibitor Drugs 0.000 claims description 2
229940122313 Nucleoside reverse transcriptase inhibitor Drugs 0.000 claims description 2
239000004030 hiv protease inhibitor Substances 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
IHCHOVVAJBADAH-UHFFFAOYSA-N n-[2-hydroxy-4-(1h-pyrazol-4-yl)phenyl]-6-methoxy-3,4-dihydro-2h-chromene-3-carboxamide Chemical compound C1C2=CC(OC)=CC=C2OCC1C(=O)NC(C(=C1)O)=CC=C1C=1C=NNC=1 IHCHOVVAJBADAH-UHFFFAOYSA-N 0.000 claims description 2
229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 claims description 2
239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 claims description 2
239000006186 oral dosage form Substances 0.000 claims description 2
239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 15
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 3
125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 2
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
230000001737 promoting effect Effects 0.000 claims 1
125000003118 aryl group Chemical group 0.000 abstract description 13
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract description 7
125000002619 bicyclic group Chemical group 0.000 abstract description 2
125000004043 oxo group Chemical group O=* 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 375
238000005481 NMR spectroscopy Methods 0.000 description 244
238000006243 chemical reaction Methods 0.000 description 201
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 170
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 163
229910001868 water Inorganic materials 0.000 description 158
239000000047 product Substances 0.000 description 154
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 136
235000019439 ethyl acetate Nutrition 0.000 description 135
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 132
101150041968 CDC13 gene Proteins 0.000 description 131
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 100
239000000243 solution Substances 0.000 description 100
229940093499 ethyl acetate Drugs 0.000 description 95
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 92
239000012267 brine Substances 0.000 description 86
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 86
238000004293 19F NMR spectroscopy Methods 0.000 description 80
239000012044 organic layer Substances 0.000 description 71
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 70
230000015572 biosynthetic process Effects 0.000 description 70
238000003786 synthesis reaction Methods 0.000 description 66
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 64
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 59
239000000651 prodrug Substances 0.000 description 58
229940002612 prodrug Drugs 0.000 description 58
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
238000000034 method Methods 0.000 description 57
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 53
239000007787 solid Substances 0.000 description 53
238000003756 stirring Methods 0.000 description 50
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 49
238000000746 purification Methods 0.000 description 49
125000002887 hydroxy group Chemical group [H]O* 0.000 description 40
239000000543 intermediate Substances 0.000 description 40
239000011541 reaction mixture Substances 0.000 description 39
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 37
150000003951 lactams Chemical class 0.000 description 37
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 36
239000012299 nitrogen atmosphere Substances 0.000 description 34
238000009472 formulation Methods 0.000 description 32
210000004027 cell Anatomy 0.000 description 31
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 31
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
239000004480 active ingredient Substances 0.000 description 30
229910052757 nitrogen Inorganic materials 0.000 description 30
239000012043 crude product Substances 0.000 description 29
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 28
239000000741 silica gel Substances 0.000 description 27
229910002027 silica gel Inorganic materials 0.000 description 27
125000006239 protecting group Chemical group 0.000 description 26
229920006395 saturated elastomer Polymers 0.000 description 26
238000004587 chromatography analysis Methods 0.000 description 25
238000010511 deprotection reaction Methods 0.000 description 24
150000002148 esters Chemical class 0.000 description 23
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 22
229910000104 sodium hydride Inorganic materials 0.000 description 22
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 22
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 20
239000007821 HATU Substances 0.000 description 20
238000012512 characterization method Methods 0.000 description 20
238000004128 high performance liquid chromatography Methods 0.000 description 20
150000001412 amines Chemical class 0.000 description 19
125000004432 carbon atom Chemical group C* 0.000 description 19
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
239000012298 atmosphere Substances 0.000 description 17
239000010410 layer Substances 0.000 description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 16
239000002253 acid Substances 0.000 description 16
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 15
229940079593 drug Drugs 0.000 description 15
229910052760 oxygen Inorganic materials 0.000 description 15
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 14
125000000623 heterocyclic group Chemical group 0.000 description 14
238000010898 silica gel chromatography Methods 0.000 description 14
229910052938 sodium sulfate Inorganic materials 0.000 description 14
235000011152 sodium sulphate Nutrition 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
238000007792 addition Methods 0.000 description 13
239000000463 material Substances 0.000 description 13
239000002480 mineral oil Substances 0.000 description 13
238000001035 drying Methods 0.000 description 12
235000010446 mineral oil Nutrition 0.000 description 12
125000001424 substituent group Chemical group 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
239000002585 base Substances 0.000 description 11
230000000875 corresponding effect Effects 0.000 description 11
238000001704 evaporation Methods 0.000 description 11
239000003921 oil Substances 0.000 description 11
210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 11
239000012312 sodium hydride Substances 0.000 description 11
229910052717 sulfur Inorganic materials 0.000 description 11
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 10
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
150000001408 amides Chemical class 0.000 description 10
238000004458 analytical method Methods 0.000 description 10
230000008020 evaporation Effects 0.000 description 10
125000001072 heteroaryl group Chemical group 0.000 description 10
150000003949 imides Chemical class 0.000 description 10
239000007788 liquid Substances 0.000 description 10
235000019198 oils Nutrition 0.000 description 10
239000012071 phase Substances 0.000 description 10
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 10
JVVRCYWZTJLJSG-UHFFFAOYSA-N 4-dimethylaminophenol Chemical compound CN(C)C1=CC=C(O)C=C1 JVVRCYWZTJLJSG-UHFFFAOYSA-N 0.000 description 9
229960000549 4-dimethylaminophenol Drugs 0.000 description 9
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-dimethylaminopyridine Substances CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 9
239000012448 Lithium borohydride Substances 0.000 description 9
235000019441 ethanol Nutrition 0.000 description 9
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 9
150000003009 phosphonic acids Chemical class 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
150000003254 radicals Chemical class 0.000 description 9
238000004007 reversed phase HPLC Methods 0.000 description 9
239000000126 substance Substances 0.000 description 9
238000010626 work up procedure Methods 0.000 description 9
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
108020004414 DNA Proteins 0.000 description 8
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
208000031886 HIV Infections Diseases 0.000 description 8
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 8
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
239000003153 chemical reaction reagent Substances 0.000 description 8
238000003776 cleavage reaction Methods 0.000 description 8
125000000524 functional group Chemical group 0.000 description 8
208000015181 infectious disease Diseases 0.000 description 8
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
230000007017 scission Effects 0.000 description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
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 7
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 7
102000004190 Enzymes Human genes 0.000 description 7
108090000790 Enzymes Proteins 0.000 description 7
239000012359 Methanesulfonyl chloride Substances 0.000 description 7
WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
238000013270 controlled release Methods 0.000 description 7
238000005859 coupling reaction Methods 0.000 description 7
239000012467 final product Substances 0.000 description 7
238000003818 flash chromatography Methods 0.000 description 7
239000003112 inhibitor Substances 0.000 description 7
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 7
229910052698 phosphorus Inorganic materials 0.000 description 7
239000000843 powder Substances 0.000 description 7
238000000926 separation method Methods 0.000 description 7
239000000725 suspension Substances 0.000 description 7
239000003039 volatile agent Substances 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
BVMWIXWOIGJRGE-UHFFFAOYSA-N NP(O)=O Chemical compound NP(O)=O BVMWIXWOIGJRGE-UHFFFAOYSA-N 0.000 description 6
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 6
125000003710 aryl alkyl group Chemical group 0.000 description 6
238000003556 assay Methods 0.000 description 6
229940125782 compound 2 Drugs 0.000 description 6
230000008878 coupling Effects 0.000 description 6
238000010168 coupling process Methods 0.000 description 6
239000006071 cream Substances 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
238000001727 in vivo Methods 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
230000010354 integration Effects 0.000 description 6
230000003834 intracellular effect Effects 0.000 description 6
150000002500 ions Chemical class 0.000 description 6
238000010791 quenching Methods 0.000 description 6
230000000171 quenching effect Effects 0.000 description 6
238000011084 recovery Methods 0.000 description 6
125000006413 ring segment Chemical group 0.000 description 6
125000000547 substituted alkyl group Chemical group 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
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229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
APPDFGHVJHZDKS-UHFFFAOYSA-M zinc;ethyl propanoate;bromide Chemical compound Br[Zn+].CCOC(=O)C[CH2-] APPDFGHVJHZDKS-UHFFFAOYSA-M 0.000 description 1