UA79470C2 - Indole, azaindole and related heterocyclic 4-alkenylpiperidine amides - Google Patents

Info

Publication number

UA79470C2

UA79470C2 UA20041210893A UA20041210893A UA79470C2 UA 79470 C2 UA79470 C2 UA 79470C2 UA 20041210893 A UA20041210893 A UA 20041210893A UA 20041210893 A UA20041210893 A UA 20041210893A UA 79470 C2 UA79470 C2 UA 79470C2

Authority

UA

Ukraine

Prior art keywords

group

heteroaryl

optionally substituted

item

compound according

Prior art date

2002-05-28

Links

• Espacenet
• Global Dossier
• Discuss

• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title description 65
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 title description 39
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title description 33
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title description 33
• 125000000623 heterocyclic group Chemical group 0.000 title description 24
• 150000001408 amides Chemical class 0.000 title description 17
• 150000001875 compounds Chemical class 0.000 claims abstract description 378
• 238000000034 method Methods 0.000 claims abstract description 250
• 208000030507 AIDS Diseases 0.000 claims abstract description 74
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 24
• 230000000840 anti-viral effect Effects 0.000 claims abstract description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
• 125000001072 heteroaryl group Chemical group 0.000 claims description 181
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 164
• -1 benzoimidazolyl Chemical group 0.000 claims description 153
• 125000000217 alkyl group Chemical group 0.000 claims description 93
• 229910052736 halogen Inorganic materials 0.000 claims description 88
• 150000002367 halogens Chemical class 0.000 claims description 86
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 74
• 125000001424 substituent group Chemical group 0.000 claims description 53
• 229910052739 hydrogen Inorganic materials 0.000 claims description 52
• 208000031886 HIV Infections Diseases 0.000 claims description 48
• 239000001257 hydrogen Substances 0.000 claims description 47
• 229910052740 iodine Inorganic materials 0.000 claims description 46
• 208000037357 HIV infectious disease Diseases 0.000 claims description 45
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 45
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 42
• 125000004076 pyridyl group Chemical group 0.000 claims description 42
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 39
• 125000002541 furyl group Chemical group 0.000 claims description 33
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 33
• 125000001544 thienyl group Chemical group 0.000 claims description 33
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 30
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 30
• 125000001425 triazolyl group Chemical group 0.000 claims description 30
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
• 125000002971 oxazolyl group Chemical group 0.000 claims description 27
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 27
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 27
• 125000002883 imidazolyl group Chemical group 0.000 claims description 26
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 25
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 25
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 25
• 125000000335 thiazolyl group Chemical group 0.000 claims description 25
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 24
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
• 150000003839 salts Chemical class 0.000 claims description 19
• 239000003112 inhibitor Substances 0.000 claims description 18
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
• 125000004193 piperazinyl group Chemical group 0.000 claims description 18
• 125000000304 alkynyl group Chemical group 0.000 claims description 17
• 229910052731 fluorine Inorganic materials 0.000 claims description 17
• 150000002431 hydrogen Chemical class 0.000 claims description 16
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
• 125000003545 alkoxy group Chemical group 0.000 claims description 15
• 239000003795 chemical substances by application Substances 0.000 claims description 15
• 229910052796 boron Inorganic materials 0.000 claims description 13
• 239000011737 fluorine Substances 0.000 claims description 12
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 12
• 241000700605 Viruses Species 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
• 125000004306 triazinyl group Chemical group 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
• 239000003443 antiviral agent Substances 0.000 claims description 7
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 6
• 239000002955 immunomodulating agent Substances 0.000 claims description 6
• 229940121354 immunomodulator Drugs 0.000 claims description 6
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
• 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 claims description 6
• 241000124008 Mammalia Species 0.000 claims description 5
• 125000004429 atom Chemical group 0.000 claims description 5
• 239000002835 hiv fusion inhibitor Substances 0.000 claims description 5
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
• JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 4
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 4
• XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 4
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 229960005475 antiinfective agent Drugs 0.000 claims description 3
• 239000004599 antimicrobial Substances 0.000 claims description 3
• 125000005872 benzooxazolyl group Chemical group 0.000 claims description 3
• 230000002584 immunomodulator Effects 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
• 125000004001 thioalkyl group Chemical group 0.000 claims description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 6
• 125000000168 pyrrolyl group Chemical group 0.000 claims 4
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
• 238000012876 topography Methods 0.000 claims 1
• 229940079593 drug Drugs 0.000 abstract description 14
• 239000003814 drug Substances 0.000 abstract description 14
• 239000000543 intermediate Substances 0.000 description 143
• 239000000203 mixture Substances 0.000 description 142
• 238000002360 preparation method Methods 0.000 description 140
• 238000006243 chemical reaction Methods 0.000 description 138
• 239000000243 solution Substances 0.000 description 104
• 239000002244 precipitate Substances 0.000 description 103
• 239000007787 solid Substances 0.000 description 91
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 73
• 239000002904 solvent Substances 0.000 description 72
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 68
• 241000282414 Homo sapiens Species 0.000 description 67
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 67
• 239000011541 reaction mixture Substances 0.000 description 63
• AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 58
• 239000002253 acid Substances 0.000 description 57
• 238000007429 general method Methods 0.000 description 55
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 52
• 230000015572 biosynthetic process Effects 0.000 description 52
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
• YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 46
• 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 description 45
• 239000003153 chemical reaction reagent Substances 0.000 description 44
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
• 239000000047 product Substances 0.000 description 38
• 235000019439 ethyl acetate Nutrition 0.000 description 35
• 238000003756 stirring Methods 0.000 description 34
• 238000003786 synthesis reaction Methods 0.000 description 34
• 125000003118 aryl group Chemical group 0.000 description 33
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 33
• 239000012044 organic layer Substances 0.000 description 32
• 239000012267 brine Substances 0.000 description 31
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 31
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 30
• 150000002475 indoles Chemical class 0.000 description 30
• 230000003993 interaction Effects 0.000 description 29
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
• 150000001412 amines Chemical class 0.000 description 26
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
• 239000007864 aqueous solution Substances 0.000 description 24
• 230000009466 transformation Effects 0.000 description 24
• 239000002585 base Substances 0.000 description 22
• 238000000746 purification Methods 0.000 description 22
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
• 239000000126 substance Substances 0.000 description 21
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 20
• 210000004027 cell Anatomy 0.000 description 20
• 238000005755 formation reaction Methods 0.000 description 20
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 20
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 19
• 238000009835 boiling Methods 0.000 description 19
• 238000005859 coupling reaction Methods 0.000 description 19
• 230000008569 process Effects 0.000 description 19
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
• 238000007792 addition Methods 0.000 description 18
• 238000010168 coupling process Methods 0.000 description 18
• 239000012074 organic phase Substances 0.000 description 18
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
• 230000008878 coupling Effects 0.000 description 17
• 150000002825 nitriles Chemical class 0.000 description 17
• 229910052757 nitrogen Inorganic materials 0.000 description 17
• 150000002148 esters Chemical class 0.000 description 16
• 229920006395 saturated elastomer Polymers 0.000 description 16
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 15
• 239000008346 aqueous phase Substances 0.000 description 15
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
• 239000010410 layer Substances 0.000 description 15
• 239000002243 precursor Substances 0.000 description 15
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 14
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 14
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
• 239000003054 catalyst Substances 0.000 description 14
• 238000003818 flash chromatography Methods 0.000 description 14
• 125000003277 amino group Chemical group 0.000 description 13
• 150000001732 carboxylic acid derivatives Chemical group 0.000 description 13
• 230000007062 hydrolysis Effects 0.000 description 13
• 238000006460 hydrolysis reaction Methods 0.000 description 13
• 229910052751 metal Inorganic materials 0.000 description 13
• 239000002184 metal Substances 0.000 description 13
• 230000003647 oxidation Effects 0.000 description 13
• 238000007254 oxidation reaction Methods 0.000 description 13
• 241000725303 Human immunodeficiency virus Species 0.000 description 12
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
• 239000012298 atmosphere Substances 0.000 description 12
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 12
• 239000000137 peptide hydrolase inhibitor Substances 0.000 description 12
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
• 238000006467 substitution reaction Methods 0.000 description 12
• 239000000725 suspension Substances 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
• 230000009467 reduction Effects 0.000 description 11
• 238000006722 reduction reaction Methods 0.000 description 11
• 238000000844 transformation Methods 0.000 description 11
• OVQAJYCAXPHYNV-UHFFFAOYSA-N 1-benzyl-3-methylpiperidin-4-one Chemical compound C1CC(=O)C(C)CN1CC1=CC=CC=C1 OVQAJYCAXPHYNV-UHFFFAOYSA-N 0.000 description 10
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
• 229910052794 bromium Inorganic materials 0.000 description 10
• 125000004432 carbon atom Chemical group C* 0.000 description 10
• 239000000460 chlorine Substances 0.000 description 10
• 239000000706 filtrate Substances 0.000 description 10
• 150000002576 ketones Chemical class 0.000 description 10
• 239000003921 oil Substances 0.000 description 10
• 239000012047 saturated solution Substances 0.000 description 10
• 239000000741 silica gel Substances 0.000 description 10
• 229910002027 silica gel Inorganic materials 0.000 description 10
• 229920002554 vinyl polymer Polymers 0.000 description 10
• 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 9
• AFAYKSMTDDLVNQ-UHFFFAOYSA-N 4-[bromo(phenyl)methylidene]piperidine-1-carboxylic acid Chemical compound OC(=O)N1CCC(CC1)=C(Br)c1ccccc1 AFAYKSMTDDLVNQ-UHFFFAOYSA-N 0.000 description 9
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
• 102100034343 Integrase Human genes 0.000 description 9
• 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 9
• 108010092799 RNA-directed DNA polymerase Proteins 0.000 description 9
• INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical class BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 9
• 229910052801 chlorine Inorganic materials 0.000 description 9
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 9
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
• 229910052727 yttrium Inorganic materials 0.000 description 9
• 241000283725 Bos Species 0.000 description 8
• 235000010469 Glycine max Nutrition 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
• 239000012043 crude product Substances 0.000 description 8
• 239000006260 foam Substances 0.000 description 8
• 239000002777 nucleoside Substances 0.000 description 8
• 150000003833 nucleoside derivatives Chemical class 0.000 description 8
• 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 8
• 239000011734 sodium Substances 0.000 description 8
• 238000010561 standard procedure Methods 0.000 description 8
• DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 description 7
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 7
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 7
• 208000007766 Kaposi sarcoma Diseases 0.000 description 7
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
• 150000007513 acids Chemical class 0.000 description 7
• 125000003368 amide group Chemical group 0.000 description 7
• 125000000524 functional group Chemical group 0.000 description 7
• 150000004820 halides Chemical class 0.000 description 7
• CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 description 7
• 229960001936 indinavir Drugs 0.000 description 7
• 239000012442 inert solvent Substances 0.000 description 7
• 208000015181 infectious disease Diseases 0.000 description 7
• 239000007788 liquid Substances 0.000 description 7
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
• 229910052700 potassium Inorganic materials 0.000 description 7
• 230000002829 reductive effect Effects 0.000 description 7
• 229910052720 vanadium Inorganic materials 0.000 description 7
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
• YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 6
• LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
• 244000068988 Glycine max Species 0.000 description 6
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