JP2005523912A5

JP2005523912A5 -

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Publication number: JP2005523912A5
Authority: JP; Japan
Prior art keywords: phosphonate; compound; acid; group; compounds
Prior art date: 2003-04-25
Legal status : Granted

Application number

JP2003587329A

Other languages

English (en)

Japanese (ja)

Other versions

JP4942915B2 (ja

JP2005523912A (ja

Filing date

2003-04-25

Publication date

2010-11-25

2003-04-25 Application filed filed Critical

2003-04-25 Priority claimed from PCT/US2003/012901 external-priority patent/WO2003090690A2/en

2005-08-11 Publication of JP2005523912A publication Critical patent/JP2005523912A/ja

2010-11-25 Publication of JP2005523912A5 publication Critical patent/JP2005523912A5/ja

2012-05-30 Application granted granted Critical

2012-05-30 Publication of JP4942915B2 publication Critical patent/JP4942915B2/ja

2023-04-25 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

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-1 hydroxy, methoxy, ethoxy, trifluoroethoxy, isopropoxy, phenoxy, benzyloxy Chemical group 0.000 claims description 485
150000001875 compounds Chemical class 0.000 claims description 286
239000000203 mixture Substances 0.000 claims description 102
150000001413 amino acids Chemical group 0.000 claims description 59
239000000651 prodrug Substances 0.000 claims description 58
229940002612 prodrug Drugs 0.000 claims description 58
239000003814 drug Substances 0.000 claims description 41
238000011282 treatment Methods 0.000 claims description 37
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 36
125000000217 alkyl group Chemical group 0.000 claims description 35
150000003839 salts Chemical class 0.000 claims description 29
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
239000000546 pharmaceutical excipient Substances 0.000 claims description 13
208000031886 HIV Infections Diseases 0.000 claims description 12
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
239000008194 pharmaceutical composition Substances 0.000 claims description 10
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 claims description 8
208000037357 HIV infectious disease Diseases 0.000 claims description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical group CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 6
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
150000004677 hydrates Chemical class 0.000 claims description 3
239000012050 conventional carrier Substances 0.000 claims description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 3
208000035475 disorder Diseases 0.000 claims 2
210000000265 leukocyte Anatomy 0.000 claims 2
238000006243 chemical reaction Methods 0.000 description 223
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical class [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 210
238000000034 method Methods 0.000 description 197
238000002360 preparation method Methods 0.000 description 158
239000000047 product Substances 0.000 description 137
150000001412 amines Chemical class 0.000 description 105
125000006239 protecting group Chemical group 0.000 description 74
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 68
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 62
150000002148 esters Chemical class 0.000 description 62
125000001424 substituent group Chemical group 0.000 description 62
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
239000002585 base Substances 0.000 description 59
230000000875 corresponding effect Effects 0.000 description 58
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
238000003786 synthesis reaction Methods 0.000 description 57
229940024606 amino acid Drugs 0.000 description 56
235000001014 amino acid Nutrition 0.000 description 56
125000003396 thiol group Chemical group [H]S* 0.000 description 52
150000001732 carboxylic acid derivatives Chemical class 0.000 description 51
239000000137 peptide hydrolase inhibitor Substances 0.000 description 48
239000002253 acid Substances 0.000 description 47
238000010511 deprotection reaction Methods 0.000 description 47
239000002243 precursor Substances 0.000 description 47
ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 46
239000004480 active ingredient Substances 0.000 description 45
108090000765 processed proteins & peptides Proteins 0.000 description 45
239000000126 substance Substances 0.000 description 44
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
239000000543 intermediate Substances 0.000 description 39
102000004196 processed proteins & peptides Human genes 0.000 description 38
238000009472 formulation Methods 0.000 description 37
150000001408 amides Chemical class 0.000 description 36
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 35
229920001184 polypeptide Polymers 0.000 description 35
230000015572 biosynthetic process Effects 0.000 description 34
229940079593 drug Drugs 0.000 description 33
229910052717 sulfur Inorganic materials 0.000 description 32
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 31
235000019441 ethanol Nutrition 0.000 description 31
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
239000002904 solvent Substances 0.000 description 30
108010010369 HIV Protease Proteins 0.000 description 29
241000725303 Human immunodeficiency virus Species 0.000 description 29
229910052799 carbon Inorganic materials 0.000 description 29
210000004027 cell Anatomy 0.000 description 28
125000000524 functional group Chemical group 0.000 description 28
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
125000004432 carbon atom Chemical group C* 0.000 description 27
125000003118 aryl group Chemical group 0.000 description 26
238000006460 hydrolysis reaction Methods 0.000 description 26
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 25
229910052757 nitrogen Inorganic materials 0.000 description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 25
102000004190 Enzymes Human genes 0.000 description 24
108090000790 Enzymes Proteins 0.000 description 24
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 24
229940124158 Protease/peptidase inhibitor Drugs 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 24
229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 24
229940088598 enzyme Drugs 0.000 description 24
230000007062 hydrolysis Effects 0.000 description 24
230000000694 effects Effects 0.000 description 23
239000003153 chemical reaction reagent Substances 0.000 description 22
238000005859 coupling reaction Methods 0.000 description 21
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 21
229910052760 oxygen Inorganic materials 0.000 description 21
239000003054 catalyst Substances 0.000 description 20
239000000243 solution Substances 0.000 description 20
239000011593 sulfur Chemical group 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
229910001868 water Inorganic materials 0.000 description 20
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 19
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 19
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 19
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 18
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 18
102000035195 Peptidases Human genes 0.000 description 18
108091005804 Peptidases Proteins 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 17
150000001721 carbon Chemical group 0.000 description 17
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
238000001727 in vivo Methods 0.000 description 16
150000007530 organic bases Chemical class 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 15
125000000623 heterocyclic group Chemical group 0.000 description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
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 15
229920006395 saturated elastomer Polymers 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
241000282414 Homo sapiens Species 0.000 description 14
230000002378 acidificating effect Effects 0.000 description 14
125000004185 ester group Chemical group 0.000 description 14
125000006413 ring segment Chemical group 0.000 description 14
230000009466 transformation Effects 0.000 description 14
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 14
102100034343 Integrase Human genes 0.000 description 13
125000003710 aryl alkyl group Chemical group 0.000 description 13
239000003795 chemical substances by application Substances 0.000 description 13
230000008878 coupling Effects 0.000 description 13
238000010168 coupling process Methods 0.000 description 13
125000005842 heteroatom Chemical group 0.000 description 13
150000002993 phenylalanine derivatives Chemical class 0.000 description 13
229910052698 phosphorus Inorganic materials 0.000 description 13
239000000758 substrate Substances 0.000 description 13
238000000844 transformation Methods 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
241001465754 Metazoa Species 0.000 description 12
108010092799 RNA-directed DNA polymerase Proteins 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
125000000539 amino acid group Chemical group 0.000 description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 12
238000003776 cleavage reaction Methods 0.000 description 12
229940125904 compound 1 Drugs 0.000 description 12
239000003112 inhibitor Substances 0.000 description 12
150000007529 inorganic bases Chemical class 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
239000003960 organic solvent Substances 0.000 description 12
239000001301 oxygen Substances 0.000 description 12
LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 12
230000002829 reductive effect Effects 0.000 description 12
238000000926 separation method Methods 0.000 description 12
239000003826 tablet Substances 0.000 description 12
150000003568 thioethers Chemical class 0.000 description 12
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
125000003342 alkenyl group Chemical group 0.000 description 11
150000002118 epoxides Chemical class 0.000 description 11
239000002207 metabolite Substances 0.000 description 11
229960005190 phenylalanine Drugs 0.000 description 11
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 11
235000008729 phenylalanine Nutrition 0.000 description 11
238000006722 reduction reaction Methods 0.000 description 11
230000007017 scission Effects 0.000 description 11
239000012279 sodium borohydride Substances 0.000 description 11
229910000033 sodium borohydride Inorganic materials 0.000 description 11
239000004365 Protease Substances 0.000 description 10
150000004657 carbamic acid derivatives Chemical class 0.000 description 10
229940125782 compound 2 Drugs 0.000 description 10
239000000194 fatty acid Substances 0.000 description 10
125000005647 linker group Chemical group 0.000 description 10
239000007788 liquid Substances 0.000 description 10
125000004437 phosphorous atom Chemical group 0.000 description 10
230000008569 process Effects 0.000 description 10
235000018102 proteins Nutrition 0.000 description 10
108090000623 proteins and genes Proteins 0.000 description 10
102000004169 proteins and genes Human genes 0.000 description 10
239000000376 reactant Substances 0.000 description 10
239000000523 sample Substances 0.000 description 10
230000001225 therapeutic effect Effects 0.000 description 10
NENLYAQPNATJSU-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline Chemical class C1NCCC2CCCCC21 NENLYAQPNATJSU-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
150000001414 amino alcohols Chemical class 0.000 description 9
239000000010 aprotic solvent Substances 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
125000004122 cyclic group Chemical group 0.000 description 9
239000012954 diazonium Substances 0.000 description 9
239000004030 hiv protease inhibitor Substances 0.000 description 9
230000003834 intracellular effect Effects 0.000 description 9
239000000463 material Substances 0.000 description 9
229910000027 potassium carbonate Inorganic materials 0.000 description 9
235000011181 potassium carbonates Nutrition 0.000 description 9
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
230000009467 reduction Effects 0.000 description 9
238000006467 substitution reaction Methods 0.000 description 9
239000000725 suspension Substances 0.000 description 9
210000001519 tissue Anatomy 0.000 description 9
QYYZXEPEVBXNNA-QGZVFWFLSA-N (1R)-2-acetyl-N-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]-5-methylsulfonyl-1,3-dihydroisoindole-1-carboxamide Chemical compound C(C)(=O)N1[C@H](C2=CC=C(C=C2C1)S(=O)(=O)C)C(=O)NC1=CC=C(C=C1)C(C(F)(F)F)(C(F)(F)F)O QYYZXEPEVBXNNA-QGZVFWFLSA-N 0.000 description 8
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 8
208000030507 AIDS Diseases 0.000 description 8
229910019142 PO4 Inorganic materials 0.000 description 8
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 8
241000700605 Viruses Species 0.000 description 8
150000007513 acids Chemical class 0.000 description 8
238000009903 catalytic hydrogenation reaction Methods 0.000 description 8
125000005843 halogen group Chemical group 0.000 description 8
125000004435 hydrogen atom Chemical class [H]* 0.000 description 8
239000012442 inert solvent Substances 0.000 description 8
239000004615 ingredient Substances 0.000 description 8
230000002401 inhibitory effect Effects 0.000 description 8
239000003921 oil Substances 0.000 description 8
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
235000019833 protease Nutrition 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
238000010992 reflux Methods 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
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 7
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 7
108010016626 Dipeptides Proteins 0.000 description 7
125000002947 alkylene group Chemical group 0.000 description 7
229940059260 amidate Drugs 0.000 description 7
125000003277 amino group Chemical class 0.000 description 7
150000008064 anhydrides Chemical class 0.000 description 7
SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 7
125000004429 atom Chemical group 0.000 description 7
150000001735 carboxylic acids Chemical class 0.000 description 7
ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
238000002648 combination therapy Methods 0.000 description 7
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210000001035 gastrointestinal tract Anatomy 0.000 description 7
238000000338 in vitro Methods 0.000 description 7
208000015181 infectious disease Diseases 0.000 description 7
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 7
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230000003287 optical effect Effects 0.000 description 7
210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 7
239000012071 phase Substances 0.000 description 7
235000021317 phosphate Nutrition 0.000 description 7
239000000843 powder Substances 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
239000004215 Carbon black (E152) Substances 0.000 description 6
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 6
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
230000000840 anti-viral effect Effects 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
244000309464 bull Species 0.000 description 6
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 6
229910000024 caesium carbonate Inorganic materials 0.000 description 6
239000000969 carrier Substances 0.000 description 6
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239000006071 cream Substances 0.000 description 6
238000006193 diazotization reaction Methods 0.000 description 6
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NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical group CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 6
239000000796 flavoring agent Substances 0.000 description 6
229930195733 hydrocarbon Natural products 0.000 description 6
238000005984 hydrogenation reaction Methods 0.000 description 6
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
230000004048 modification Effects 0.000 description 6
238000012986 modification Methods 0.000 description 6
239000002777 nucleoside Substances 0.000 description 6
150000003833 nucleoside derivatives Chemical class 0.000 description 6
230000003647 oxidation Effects 0.000 description 6
238000007254 oxidation reaction Methods 0.000 description 6
230000036961 partial effect Effects 0.000 description 6
150000002989 phenols Chemical class 0.000 description 6
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 6
239000003755 preservative agent Substances 0.000 description 6
235000019419 proteases Nutrition 0.000 description 6
229910000029 sodium carbonate Inorganic materials 0.000 description 6
239000003765 sweetening agent Substances 0.000 description 6
230000032258 transport Effects 0.000 description 6
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
229920002554 vinyl polymer Polymers 0.000 description 6
230000003612 virological effect Effects 0.000 description 6
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 5
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
108090000371 Esterases Proteins 0.000 description 5
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 5
229940122440 HIV protease inhibitor Drugs 0.000 description 5
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JP2003587329A 2002-04-26 2003-04-25 Ｈｉｖプロテアーゼ阻害剤化合物のホスホネートアナログの細胞蓄積 Expired - Lifetime JP4942915B2 (ja)