SK76093A3 - Aminediol protease inhibitors - Google Patents

Info

Publication number

SK76093A3

SK76093A3 SK76093A SK76093A SK76093A3 SK 76093 A3 SK76093 A3 SK 76093A3 SK 76093 A SK76093 A SK 76093A SK 76093 A SK76093 A SK 76093A SK 76093 A3 SK76093 A3 SK 76093A3

Authority

SK

Slovakia

Prior art keywords

compound

mmol

hydroxy

group

meoh

Prior art date

1992-07-20

Links

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• 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 title 1
• 239000000137 peptide hydrolase inhibitor Substances 0.000 title 1
• 238000000034 method Methods 0.000 claims abstract description 216
• 150000001875 compounds Chemical class 0.000 claims abstract description 173
• 239000000203 mixture Substances 0.000 claims abstract description 20
• -1 1,1-dimethylethyl ester Chemical class 0.000 claims description 112
• 229910052739 hydrogen Inorganic materials 0.000 claims description 68
• 238000002360 preparation method Methods 0.000 claims description 40
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
• 239000000243 solution Substances 0.000 claims description 24
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
• 125000000623 heterocyclic group Chemical group 0.000 claims description 16
• 239000007787 solid Substances 0.000 claims description 14
• 239000003795 chemical substances by application Substances 0.000 claims description 13
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 13
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 8
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
• 239000012267 brine Substances 0.000 claims description 3
• 239000002245 particle Substances 0.000 claims description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 3
• KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
• 229910004298 SiO 2 Inorganic materials 0.000 claims 6
• CELPHAGZKFMOMR-UHFFFAOYSA-N azanium;dichloromethane;methanol;hydroxide Chemical compound [NH4+].[OH-].OC.ClCCl CELPHAGZKFMOMR-UHFFFAOYSA-N 0.000 claims 6
• 238000003818 flash chromatography Methods 0.000 claims 6
• 238000002844 melting Methods 0.000 claims 6
• 230000008018 melting Effects 0.000 claims 6
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 5
• 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 claims 5
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 4
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 4
• GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 claims 4
• 239000000741 silica gel Substances 0.000 claims 4
• 229910002027 silica gel Inorganic materials 0.000 claims 4
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 3
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 claims 3
• 239000000463 material Substances 0.000 claims 3
• 239000003921 oil Substances 0.000 claims 3
• LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 claims 2
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 2
• 238000000921 elemental analysis Methods 0.000 claims 2
• 235000019439 ethyl acetate Nutrition 0.000 claims 2
• 229910052943 magnesium sulfate Inorganic materials 0.000 claims 2
• 235000019341 magnesium sulphate Nutrition 0.000 claims 2
• 239000012074 organic phase Substances 0.000 claims 2
• 238000012746 preparative thin layer chromatography Methods 0.000 claims 2
• 239000003039 volatile agent Substances 0.000 claims 2
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 1
• KNSPBSQWRKKAPI-UHFFFAOYSA-N 2,2-dimethylcyclohexan-1-one Chemical compound CC1(C)CCCCC1=O KNSPBSQWRKKAPI-UHFFFAOYSA-N 0.000 claims 1
• YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 claims 1
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims 1
• 238000004587 chromatography analysis Methods 0.000 claims 1
• 239000012230 colorless oil Substances 0.000 claims 1
• 239000012043 crude product Substances 0.000 claims 1
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims 1
• 239000010410 layer Substances 0.000 claims 1
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
• 239000012044 organic layer Substances 0.000 claims 1
• 229920000642 polymer Polymers 0.000 claims 1
• 238000002953 preparative HPLC Methods 0.000 claims 1
• DSXFPRKPFJRPIB-UHFFFAOYSA-N thiolan-3-one Chemical compound O=C1CCSC1 DSXFPRKPFJRPIB-UHFFFAOYSA-N 0.000 claims 1
• KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims 1
• 108091005804 Peptidases Proteins 0.000 abstract description 16
• 239000004365 Protease Substances 0.000 abstract description 15
• 230000001177 retroviral effect Effects 0.000 abstract description 11
• 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 abstract description 10
• 208000030507 AIDS Diseases 0.000 abstract description 8
• 208000031886 HIV Infections Diseases 0.000 abstract description 7
• 230000005764 inhibitory process Effects 0.000 abstract description 4
• 125000000217 alkyl group Chemical group 0.000 description 111
• 238000006243 chemical reaction Methods 0.000 description 95
• 239000001257 hydrogen Substances 0.000 description 67
• 125000003118 aryl group Chemical group 0.000 description 44
• 150000002924 oxiranes Chemical class 0.000 description 42
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 41
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 37
• 150000001412 amines Chemical class 0.000 description 37
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 32
• 229940024606 amino acid Drugs 0.000 description 28
• 235000001014 amino acid Nutrition 0.000 description 28
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 27
• 230000009467 reduction Effects 0.000 description 27
• 238000006722 reduction reaction Methods 0.000 description 27
• 125000003342 alkenyl group Chemical group 0.000 description 25
• 239000002585 base Substances 0.000 description 23
• 125000000753 cycloalkyl group Chemical group 0.000 description 23
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 23
• 108090000765 processed proteins & peptides Proteins 0.000 description 23
• 125000006239 protecting group Chemical group 0.000 description 23
• 125000003545 alkoxy group Chemical group 0.000 description 18
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 16
• 150000001414 amino alcohols Chemical class 0.000 description 15
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 14
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
• 238000003776 cleavage reaction Methods 0.000 description 14
• 230000007017 scission Effects 0.000 description 14
• 229910052757 nitrogen Inorganic materials 0.000 description 13
• 125000004043 oxo group Chemical group O=* 0.000 description 13
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
• 150000001336 alkenes Chemical class 0.000 description 12
• 125000004429 atom Chemical group 0.000 description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
• 230000008569 process Effects 0.000 description 12
• 230000002829 reductive effect Effects 0.000 description 12
• 150000001413 amino acids Chemical class 0.000 description 11
• 125000003277 amino group Chemical group 0.000 description 11
• 239000003153 chemical reaction reagent Substances 0.000 description 11
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 11
• 150000003839 salts Chemical class 0.000 description 11
• 239000011734 sodium Substances 0.000 description 11
• 125000001424 substituent group Chemical group 0.000 description 11
• 238000003786 synthesis reaction Methods 0.000 description 11
• 241000725303 Human immunodeficiency virus Species 0.000 description 10
• 239000000460 chlorine Substances 0.000 description 10
• 239000000543 intermediate Substances 0.000 description 10
• 229910052760 oxygen Inorganic materials 0.000 description 10
• 239000001301 oxygen Substances 0.000 description 10
• 241001430294 unidentified retrovirus Species 0.000 description 10
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 9
• 125000000304 alkynyl group Chemical group 0.000 description 9
• 125000004104 aryloxy group Chemical group 0.000 description 9
• 230000015572 biosynthetic process Effects 0.000 description 9
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
• 238000009833 condensation Methods 0.000 description 9
• 230000005494 condensation Effects 0.000 description 9
• 150000003944 halohydrins Chemical class 0.000 description 9
• 230000003647 oxidation Effects 0.000 description 9
• 238000007254 oxidation reaction Methods 0.000 description 9
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 8
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 8
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 8
• 229910052794 bromium Inorganic materials 0.000 description 8
• 229910052799 carbon Inorganic materials 0.000 description 8
• 125000004432 carbon atom Chemical group C* 0.000 description 8
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 description 8
• 239000011591 potassium Substances 0.000 description 8
• 229910052700 potassium Inorganic materials 0.000 description 8
• 238000006268 reductive amination reaction Methods 0.000 description 8
• 229910052708 sodium Inorganic materials 0.000 description 8
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 7
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 7
• 125000004414 alkyl thio group Chemical group 0.000 description 7
• 125000003710 aryl alkyl group Chemical group 0.000 description 7
• 150000001721 carbon Chemical group 0.000 description 7
• 125000004122 cyclic group Chemical group 0.000 description 7
• 150000002009 diols Chemical class 0.000 description 7
• 239000003814 drug Substances 0.000 description 7
• 150000002576 ketones Chemical class 0.000 description 7
• 125000002950 monocyclic group Chemical group 0.000 description 7
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• 241000700605 Viruses Species 0.000 description 6
• 238000007239 Wittig reaction Methods 0.000 description 6
• 125000002947 alkylene group Chemical group 0.000 description 6
• 229910021529 ammonia Inorganic materials 0.000 description 6
• 125000005110 aryl thio group Chemical group 0.000 description 6
• 125000004093 cyano group Chemical group *C#N 0.000 description 6
• 150000002148 esters Chemical class 0.000 description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
• 125000005843 halogen group Chemical group 0.000 description 6
• 239000008194 pharmaceutical composition Substances 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• 230000010076 replication Effects 0.000 description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
• 102000004190 Enzymes Human genes 0.000 description 5
• 108090000790 Enzymes Proteins 0.000 description 5
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
• 102100034343 Integrase Human genes 0.000 description 5
• 102000035195 Peptidases Human genes 0.000 description 5
• 206010038997 Retroviral infections Diseases 0.000 description 5
• 125000005199 aryl carbonyloxy group Chemical group 0.000 description 5
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 5
• 125000002837 carbocyclic group Chemical group 0.000 description 5
• MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 5
• 238000005859 coupling reaction Methods 0.000 description 5
• 239000003085 diluting agent Substances 0.000 description 5
• 125000005842 heteroatom Chemical group 0.000 description 5
• 125000004470 heterocyclooxy group Chemical group 0.000 description 5
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 5
• 230000002401 inhibitory effect Effects 0.000 description 5
• 229910052740 iodine Inorganic materials 0.000 description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
• 239000002243 precursor Substances 0.000 description 5
• 150000003141 primary amines Chemical class 0.000 description 5
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 5
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 5
• 229920006395 saturated elastomer Polymers 0.000 description 5
• 229910052717 sulfur Inorganic materials 0.000 description 5
• 239000011593 sulfur Substances 0.000 description 5
• 125000000335 thiazolyl group Chemical group 0.000 description 5
• 125000004665 trialkylsilyl group Chemical group 0.000 description 5
• IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
• 229910014033 C-OH Inorganic materials 0.000 description 4
• 229910014570 C—OH Inorganic materials 0.000 description 4
• 108020004414 DNA Proteins 0.000 description 4
• 108010010369 HIV Protease Proteins 0.000 description 4
• 102000006992 Interferon-alpha Human genes 0.000 description 4
• 108010047761 Interferon-alpha Proteins 0.000 description 4
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
• XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
• 125000002619 bicyclic group Chemical group 0.000 description 4
• SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
• 239000003638 chemical reducing agent Substances 0.000 description 4
• 229910052801 chlorine Inorganic materials 0.000 description 4
• 230000008878 coupling Effects 0.000 description 4
• 238000010168 coupling process Methods 0.000 description 4
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
• 229940079593 drug Drugs 0.000 description 4
• 125000002541 furyl group Chemical group 0.000 description 4
• 229910052736 halogen Inorganic materials 0.000 description 4
• 150000002367 halogens Chemical class 0.000 description 4
• 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
• 229910052744 lithium Inorganic materials 0.000 description 4
• 239000012280 lithium aluminium hydride Substances 0.000 description 4
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
• 238000004519 manufacturing process Methods 0.000 description 4
• 229910052751 metal Inorganic materials 0.000 description 4
• 239000002184 metal Substances 0.000 description 4
• GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 4
• NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 4
• 125000000160 oxazolidinyl group Chemical group 0.000 description 4
• 239000012286 potassium permanganate Substances 0.000 description 4
• 230000002265 prevention Effects 0.000 description 4
• JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
• 239000002904 solvent Substances 0.000 description 4
• 239000000725 suspension Substances 0.000 description 4
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
• 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 3
• UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 description 3
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 3
• IVRMZWNICZWHMI-UHFFFAOYSA-N Azide Chemical compound [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 3
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
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