BRPI0311541B1 - Compostos de indol, azaindol e 4-alque-nil piperidina amidas heterocíclicas relacionadas e uso destes - Google Patents

Info

Publication number

BRPI0311541B1

BRPI0311541B1 BRPI0311541-0A BRPI0311541A BRPI0311541B1 BR PI0311541 B1 BRPI0311541 B1 BR PI0311541B1 BR PI0311541 A BRPI0311541 A BR PI0311541A BR PI0311541 B1 BRPI0311541 B1 BR PI0311541B1

Authority

BR

Brazil

Prior art keywords

scheme

chem

group

compounds

azaindole

Prior art date

2002-05-28

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 285
• -1 heterocyclic amides Chemical class 0.000 title abstract description 201
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title abstract description 66
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 title abstract description 51
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title abstract description 36
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title abstract description 36
• NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title abstract description 23
• 238000011282 treatment Methods 0.000 claims abstract description 24
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
• 238000002360 preparation method Methods 0.000 claims description 178
• 241000700605 Viruses Species 0.000 claims description 8
• 241000124008 Mammalia Species 0.000 claims description 3
• 238000000034 method Methods 0.000 abstract description 233
• 208000030507 AIDS Diseases 0.000 abstract description 79
• 239000003814 drug Substances 0.000 abstract description 19
• 229940079593 drug Drugs 0.000 abstract description 17
• 230000000840 anti-viral effect Effects 0.000 abstract description 12
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 171
• 238000006243 chemical reaction Methods 0.000 description 166
• 239000000203 mixture Substances 0.000 description 142
• 239000000543 intermediate Substances 0.000 description 136
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 135
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 103
• 239000000243 solution Substances 0.000 description 103
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 98
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 95
• 239000007787 solid Substances 0.000 description 91
• 239000002904 solvent Substances 0.000 description 77
• 125000001072 heteroaryl group Chemical group 0.000 description 68
• 238000005160 1H NMR spectroscopy Methods 0.000 description 67
• 235000019439 ethyl acetate Nutrition 0.000 description 65
• 238000005859 coupling reaction Methods 0.000 description 60
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 58
• 238000010168 coupling process Methods 0.000 description 55
• 238000007429 general method Methods 0.000 description 55
• 230000008878 coupling Effects 0.000 description 54
• 239000002253 acid Substances 0.000 description 53
• 125000000217 alkyl group Chemical group 0.000 description 50
• 125000005334 azaindolyl group Chemical class N1N=C(C2=CC=CC=C12)* 0.000 description 47
• 239000011734 sodium Substances 0.000 description 47
• 238000005481 NMR spectroscopy Methods 0.000 description 46
• 230000015572 biosynthetic process Effects 0.000 description 46
• 239000003153 chemical reaction reagent Substances 0.000 description 46
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 46
• 239000000460 chlorine Substances 0.000 description 44
• 125000003118 aryl group Chemical group 0.000 description 42
• 238000002953 preparative HPLC Methods 0.000 description 42
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 38
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 37
• 238000003786 synthesis reaction Methods 0.000 description 37
• 0 CCCC(CC)[C@](*(C)C)C1CCNCC1 Chemical compound CCCC(CC)[C@](*(C)C)C1CCNCC1 0.000 description 36
• 125000000623 heterocyclic group Chemical group 0.000 description 36
• 241000725303 Human immunodeficiency virus Species 0.000 description 35
• 238000003756 stirring Methods 0.000 description 34
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 34
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 33
• 150000001299 aldehydes Chemical class 0.000 description 32
• 239000012267 brine Substances 0.000 description 32
• 239000012044 organic layer Substances 0.000 description 32
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 32
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
• 208000031886 HIV Infections Diseases 0.000 description 31
• 229910052736 halogen Inorganic materials 0.000 description 30
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 29
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
• HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 29
• 208000037357 HIV infectious disease Diseases 0.000 description 28
• 150000002367 halogens Chemical class 0.000 description 28
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 28
• 229910052739 hydrogen Inorganic materials 0.000 description 28
• 150000002475 indoles Chemical class 0.000 description 28
• 208000015181 infectious disease Diseases 0.000 description 28
• 239000011541 reaction mixture Substances 0.000 description 28
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 27
• 150000001412 amines Chemical class 0.000 description 27
• 239000000047 product Substances 0.000 description 27
• ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 26
• 239000002585 base Substances 0.000 description 25
• 229910052801 chlorine Inorganic materials 0.000 description 24
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 23
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 23
• 229910052794 bromium Inorganic materials 0.000 description 23
• 229960002555 zidovudine Drugs 0.000 description 23
• 239000001257 hydrogen Substances 0.000 description 22
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 22
• 238000000746 purification Methods 0.000 description 22
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• 150000001408 amides Chemical class 0.000 description 21
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 20
• 229920006395 saturated elastomer Polymers 0.000 description 20
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 19
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
• 229920002472 Starch Polymers 0.000 description 19
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 19
• 125000001424 substituent group Chemical group 0.000 description 19
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 18
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 18
• 229910052757 nitrogen Inorganic materials 0.000 description 18
• 239000012074 organic phase Substances 0.000 description 18
• 239000008107 starch Substances 0.000 description 18
• 230000009466 transformation Effects 0.000 description 18
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 17
• 150000002825 nitriles Chemical class 0.000 description 17
• 239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 17
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 16
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 16
• 229910004298 SiO 2 Inorganic materials 0.000 description 16
• 125000000753 cycloalkyl group Chemical group 0.000 description 16
• 150000002148 esters Chemical class 0.000 description 16
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 16
• 125000005190 thiohydroxy group Chemical group 0.000 description 16
• BXVSAYBZSGIURM-UHFFFAOYSA-N 2-phenoxy-4h-1,3,2$l^{5}-benzodioxaphosphinine 2-oxide Chemical compound O1CC2=CC=CC=C2OP1(=O)OC1=CC=CC=C1 BXVSAYBZSGIURM-UHFFFAOYSA-N 0.000 description 15
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
• 125000003545 alkoxy group Chemical group 0.000 description 15
• 239000008346 aqueous phase Substances 0.000 description 15
• 210000004027 cell Anatomy 0.000 description 15
• 239000010410 layer Substances 0.000 description 15
• 239000002243 precursor Substances 0.000 description 15
• 239000003054 catalyst Substances 0.000 description 14
• 238000003818 flash chromatography Methods 0.000 description 14
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 14
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 13
• WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 description 13
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 13
• 239000003795 chemical substances by application Substances 0.000 description 13
• 125000004093 cyano group Chemical group *C#N 0.000 description 13
• 229910052731 fluorine Inorganic materials 0.000 description 13
• 238000005755 formation reaction Methods 0.000 description 13
• 230000014759 maintenance of location Effects 0.000 description 13
• 230000001404 mediated effect Effects 0.000 description 13
• 229910052751 metal Inorganic materials 0.000 description 13
• 239000002184 metal Substances 0.000 description 13
• 238000010992 reflux Methods 0.000 description 13
• 150000003839 salts Chemical class 0.000 description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 12
• 150000001204 N-oxides Chemical class 0.000 description 12
• 125000003277 amino group Chemical group 0.000 description 12
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 12
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 12
• AJDPNPAGZMZOMN-UHFFFAOYSA-N diethyl (4-oxo-1,2,3-benzotriazin-3-yl) phosphate Chemical compound C1=CC=C2C(=O)N(OP(=O)(OCC)OCC)N=NC2=C1 AJDPNPAGZMZOMN-UHFFFAOYSA-N 0.000 description 12
• 239000003112 inhibitor Substances 0.000 description 12
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
• 229910052763 palladium Inorganic materials 0.000 description 12
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• 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 12
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 11
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
• 229910052799 carbon Inorganic materials 0.000 description 11
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 11
• 150000004820 halides Chemical class 0.000 description 11
• 238000004811 liquid chromatography Methods 0.000 description 11
• 229910052744 lithium Inorganic materials 0.000 description 11
• 239000003921 oil Substances 0.000 description 11
• 239000000137 peptide hydrolase inhibitor Substances 0.000 description 11
• 238000000844 transformation Methods 0.000 description 11
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
• 244000309464 bull Species 0.000 description 10
• 239000000706 filtrate Substances 0.000 description 10
• 150000002576 ketones Chemical class 0.000 description 10
• DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 10
• 230000009467 reduction Effects 0.000 description 10
• 238000006722 reduction reaction Methods 0.000 description 10
• 239000000725 suspension Substances 0.000 description 10
• 125000001544 thienyl group Chemical group 0.000 description 10
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 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
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 9
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
• 239000007864 aqueous solution Substances 0.000 description 9
• INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical class BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 9
• 125000004432 carbon atom Chemical group C* 0.000 description 9
• 239000010949 copper Substances 0.000 description 9
• 230000007062 hydrolysis Effects 0.000 description 9
• 238000006460 hydrolysis reaction Methods 0.000 description 9
• 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 9
• 229960001936 indinavir Drugs 0.000 description 9
• 125000001786 isothiazolyl group Chemical group 0.000 description 9
• 125000000842 isoxazolyl group Chemical group 0.000 description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
• 125000003226 pyrazolyl group Chemical group 0.000 description 9
• 125000004076 pyridyl group Chemical group 0.000 description 9
• 239000000741 silica gel Substances 0.000 description 9
• 229910002027 silica gel Inorganic materials 0.000 description 9
• 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 9
• 125000003831 tetrazolyl group Chemical group 0.000 description 9
• 125000001113 thiadiazolyl group Chemical group 0.000 description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
• 102100034343 Integrase Human genes 0.000 description 8
• 229940122313 Nucleoside reverse transcriptase inhibitor Drugs 0.000 description 8
• 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 8
• 108010092799 RNA-directed DNA polymerase Proteins 0.000 description 8
• 238000006619 Stille reaction Methods 0.000 description 8
• 150000001336 alkenes Chemical class 0.000 description 8
• 229910052796 boron Inorganic materials 0.000 description 8
• 238000001816 cooling Methods 0.000 description 8
• 230000000694 effects Effects 0.000 description 8
• 125000002541 furyl group Chemical group 0.000 description 8
• 239000007789 gas Substances 0.000 description 8
• 150000002431 hydrogen Chemical class 0.000 description 8
• 125000002883 imidazolyl group Chemical group 0.000 description 8
• 239000012442 inert solvent Substances 0.000 description 8
• 229910052740 iodine Inorganic materials 0.000 description 8
• 239000007788 liquid Substances 0.000 description 8
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 8
• 125000001715 oxadiazolyl group Chemical group 0.000 description 8
• 125000002971 oxazolyl group Chemical group 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
• 125000002098 pyridazinyl group Chemical group 0.000 description 8
• 239000007858 starting material Substances 0.000 description 8
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 8
• NBRIZDGVBLBLLZ-UHFFFAOYSA-N tert-butyl 4-[bromo(phenyl)methylidene]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1=C(Br)C1=CC=CC=C1 NBRIZDGVBLBLLZ-UHFFFAOYSA-N 0.000 description 8
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 7
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 7
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
• 206010039491 Sarcoma Diseases 0.000 description 7
• WMHSRBZIJNQHKT-FFKFEZPRSA-N abacavir sulfate Chemical compound OS(O)(=O)=O.C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1.C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 WMHSRBZIJNQHKT-FFKFEZPRSA-N 0.000 description 7
• 230000010933 acylation Effects 0.000 description 7
• 238000005917 acylation reaction Methods 0.000 description 7
• 125000000304 alkynyl group Chemical group 0.000 description 7
• 239000003443 antiviral agent Substances 0.000 description 7
• 238000010276 construction Methods 0.000 description 7
• WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CC1 WHBIGIKBNXZKFE-UHFFFAOYSA-N 0.000 description 7
• XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 description 7
• 239000011737 fluorine Substances 0.000 description 7
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 7
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 7
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 7
• 239000000463 material Substances 0.000 description 7
• 230000003647 oxidation Effects 0.000 description 7
• 238000007254 oxidation reaction Methods 0.000 description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 description 7
• 235000019698 starch Nutrition 0.000 description 7
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 7
• 125000000335 thiazolyl group Chemical group 0.000 description 7
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