CZ143793A3

CZ143793A3 - Aminediole inhibitors of protease

Aminediole inhibitors of protease Download PDF

Info

Publication number: CZ143793A3
Authority: CZ; Czechia
Prior art keywords: group; alkyl; hydrogen; compound; lower alkyl
Prior art date: 1992-07-20

Application number

CZ931437A

Other languages

Czech (cs)

English (en)

Inventor

Eric M Gordon

Joel C Barrish

Gregory S Bisacchi

Chong-Qing Sun

Joseph A Tino

Gregory D Vite

Robert Zahler

Original Assignee

Squibb & Sons Inc

Priority date

1992-07-20

Filing date

1993-07-19

Publication date

1995-02-15

1993-07-19 Application filed by Squibb & Sons Inc filed Critical Squibb & Sons Inc

1995-02-15 Publication of CZ143793A3 publication Critical patent/CZ143793A3/cs

Links

108091005804 Peptidases Proteins 0.000 title abstract description 13
239000004365 Protease Substances 0.000 title abstract description 12
102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 title abstract description 8
239000003112 inhibitor Substances 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 836
-1 or two of R 5 Chemical compound 0.000 claims description 164
125000000217 alkyl group Chemical group 0.000 claims description 129
229910052799 carbon Inorganic materials 0.000 claims description 119
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 98
229910052739 hydrogen Inorganic materials 0.000 claims description 93
239000001257 hydrogen Substances 0.000 claims description 77
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
125000003118 aryl group Chemical group 0.000 claims description 33
150000002431 hydrogen Chemical class 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 24
229910052717 sulfur Inorganic materials 0.000 claims description 24
125000003545 alkoxy group Chemical group 0.000 claims description 23
229910052760 oxygen Inorganic materials 0.000 claims description 21
125000003342 alkenyl group Chemical group 0.000 claims description 20
125000000753 cycloalkyl group Chemical group 0.000 claims description 18
125000004429 atom Chemical group 0.000 claims description 16
150000001413 amino acids Chemical class 0.000 claims description 15
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
125000000623 heterocyclic group Chemical group 0.000 claims description 15
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
239000001301 oxygen Substances 0.000 claims description 13
108090000765 processed proteins & peptides Proteins 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
239000011593 sulfur Substances 0.000 claims description 8
125000002837 carbocyclic group Chemical group 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
125000000468 ketone group Chemical group 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 2
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 2
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
125000005111 carboxyalkoxy group Chemical group 0.000 claims 1
238000000034 method Methods 0.000 abstract description 257
239000000203 mixture Substances 0.000 abstract description 208
208000031886 HIV Infections Diseases 0.000 abstract description 6
230000001177 retroviral effect Effects 0.000 abstract description 6
208000030507 AIDS Diseases 0.000 abstract description 5
230000005764 inhibitory process Effects 0.000 abstract description 5
238000002360 preparation method Methods 0.000 description 263
239000007787 solid Substances 0.000 description 174
238000006243 chemical reaction Methods 0.000 description 166
239000000243 solution Substances 0.000 description 165
239000000460 chlorine Substances 0.000 description 133
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 129
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 116
YRTFLDFDKPFNCJ-UHFFFAOYSA-N 1-[4-amino-2,6-di(propan-2-yl)phenyl]-3-[1-butyl-2-oxo-4-[3-(3-pyrrolidin-1-ylpropoxy)phenyl]-1,8-naphthyridin-3-yl]urea;dihydrochloride Chemical compound Cl.Cl.CC(C)C=1C=C(N)C=C(C(C)C)C=1NC(=O)NC=1C(=O)N(CCCC)C2=NC=CC=C2C=1C(C=1)=CC=CC=1OCCCN1CCCC1 YRTFLDFDKPFNCJ-UHFFFAOYSA-N 0.000 description 110
239000002253 acid Substances 0.000 description 107
238000004458 analytical method Methods 0.000 description 106
230000015572 biosynthetic process Effects 0.000 description 89
238000003786 synthesis reaction Methods 0.000 description 78
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 77
238000002844 melting Methods 0.000 description 74
230000008018 melting Effects 0.000 description 74
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 71
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 56
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
150000001412 amines Chemical class 0.000 description 54
235000019439 ethyl acetate Nutrition 0.000 description 54
239000011541 reaction mixture Substances 0.000 description 53
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 52
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 49
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 49
239000012267 brine Substances 0.000 description 48
229910052757 nitrogen Inorganic materials 0.000 description 48
239000000741 silica gel Substances 0.000 description 46
229910002027 silica gel Inorganic materials 0.000 description 46
239000011734 sodium Substances 0.000 description 44
229910001868 water Inorganic materials 0.000 description 44
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 42
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 41
150000002118 epoxides Chemical class 0.000 description 38
229920006395 saturated elastomer Polymers 0.000 description 38
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 37
239000006260 foam Substances 0.000 description 37
239000003921 oil Substances 0.000 description 35
235000019198 oils Nutrition 0.000 description 33
150000002500 ions Chemical class 0.000 description 30
239000012044 organic layer Substances 0.000 description 30
238000000921 elemental analysis Methods 0.000 description 29
239000000126 substance Substances 0.000 description 29
101100289061 Drosophila melanogaster lili gene Proteins 0.000 description 28
241000406668 Loxodonta cyclotis Species 0.000 description 28
238000009833 condensation Methods 0.000 description 28
239000010410 layer Substances 0.000 description 28
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
230000005494 condensation Effects 0.000 description 27
230000008569 process Effects 0.000 description 27
230000002829 reductive effect Effects 0.000 description 27
229940024606 amino acid Drugs 0.000 description 26
238000003756 stirring Methods 0.000 description 26
229910052740 iodine Inorganic materials 0.000 description 24
239000000047 product Substances 0.000 description 24
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 23
239000000284 extract Substances 0.000 description 23
230000009467 reduction Effects 0.000 description 23
238000006722 reduction reaction Methods 0.000 description 23
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
235000001014 amino acid Nutrition 0.000 description 22
239000002585 base Substances 0.000 description 22
101150052863 THY1 gene Proteins 0.000 description 21
239000002904 solvent Substances 0.000 description 21
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 21
RIZMRRKBZQXFOY-UHFFFAOYSA-N ethion Chemical compound CCOP(=S)(OCC)SCSP(=S)(OCC)OCC RIZMRRKBZQXFOY-UHFFFAOYSA-N 0.000 description 20
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 20
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 20
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
239000012230 colorless oil Substances 0.000 description 18
239000000725 suspension Substances 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
238000005481 NMR spectroscopy Methods 0.000 description 17
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
239000004927 clay Substances 0.000 description 17
238000003818 flash chromatography Methods 0.000 description 17
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 description 16
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
150000001299 aldehydes Chemical class 0.000 description 16
239000011575 calcium Substances 0.000 description 16
125000001309 chloro group Chemical group Cl* 0.000 description 16
239000003814 drug Substances 0.000 description 16
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 15
101100518501 Mus musculus Spp1 gene Proteins 0.000 description 15
150000001732 carboxylic acid derivatives Chemical class 0.000 description 15
238000004587 chromatography analysis Methods 0.000 description 15
150000002148 esters Chemical class 0.000 description 15
YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 14
238000010828 elution Methods 0.000 description 14
125000006239 protecting group Chemical group 0.000 description 14
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
238000003776 cleavage reaction Methods 0.000 description 13
239000000706 filtrate Substances 0.000 description 13
229910052700 potassium Inorganic materials 0.000 description 13
230000007017 scission Effects 0.000 description 13
229910052708 sodium Inorganic materials 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 12
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
239000012298 atmosphere Substances 0.000 description 11
125000004043 oxo group Chemical group O=* 0.000 description 11
239000011591 potassium Substances 0.000 description 11
239000011669 selenium Substances 0.000 description 11
HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 10
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 10
239000010936 titanium Substances 0.000 description 10
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
241000282414 Homo sapiens Species 0.000 description 9
150000007513 acids Chemical class 0.000 description 9
230000009471 action Effects 0.000 description 9
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 9
239000011651 chromium Substances 0.000 description 9
229940125904 compound 1 Drugs 0.000 description 9
125000004122 cyclic group Chemical group 0.000 description 9
238000001035 drying Methods 0.000 description 9
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
239000000377 silicon dioxide Substances 0.000 description 9
239000011701 zinc Substances 0.000 description 9
229910052725 zinc Inorganic materials 0.000 description 9
241000725303 Human immunodeficiency virus Species 0.000 description 8
241000234435 Lilium Species 0.000 description 8
241001024304 Mino Species 0.000 description 8
241000283080 Proboscidea <mammal> Species 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 8
230000002378 acidificating effect Effects 0.000 description 8
150000001336 alkenes Chemical class 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
239000003153 chemical reaction reagent Substances 0.000 description 8
229910052801 chlorine Inorganic materials 0.000 description 8
229940126214 compound 3 Drugs 0.000 description 8
238000001816 cooling Methods 0.000 description 8
239000012043 crude product Substances 0.000 description 8
229940079593 drug Drugs 0.000 description 8
229910052744 lithium Inorganic materials 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
239000000463 material Substances 0.000 description 8
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 8
238000004809 thin layer chromatography Methods 0.000 description 8
HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 7
QXOGPTXQGKQSJT-UHFFFAOYSA-N 1-amino-4-[4-(3,4-dimethylphenyl)sulfanylanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound Cc1ccc(Sc2ccc(Nc3cc(c(N)c4C(=O)c5ccccc5C(=O)c34)S(O)(=O)=O)cc2)cc1C QXOGPTXQGKQSJT-UHFFFAOYSA-N 0.000 description 7
241000282472 Canis lupus familiaris Species 0.000 description 7
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 7
OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 7
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
241000700605 Viruses Species 0.000 description 7
125000005196 alkyl carbonyloxy group Chemical group 0.000 description 7
229940126086 compound 21 Drugs 0.000 description 7
239000010779 crude oil Substances 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
150000004678 hydrides Chemical class 0.000 description 7
239000000543 intermediate Substances 0.000 description 7
TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 7
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 7
210000000056 organ Anatomy 0.000 description 7
239000003208 petroleum Substances 0.000 description 7
239000012071 phase Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical class [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 7
239000008279 sol Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
229910014033 C-OH Inorganic materials 0.000 description 6
BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 description 6
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 6
229910014570 C—OH Inorganic materials 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 6
AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 6
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
241000282320 Panthera leo Species 0.000 description 6
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