EA011399B1 - Трициклические соединения - ингибиторы интегразы вич, способ их получения (варианты), фармацевтическая композиция на их основе, способ ее получения и способы их использования в лечении болезней - Google Patents

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Publication number

EA011399B1

EA011399B1 EA200500660A EA200500660A EA011399B1 EA 011399 B1 EA011399 B1 EA 011399B1 EA 200500660 A EA200500660 A EA 200500660A EA 200500660 A EA200500660 A EA 200500660A EA 011399 B1 EA011399 B1 EA 011399B1

Authority

EA

Eurasian Patent Office

Prior art keywords

substituted

alkyl

aryl

group

compound according

Prior art date

2002-10-16

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 312
• 238000000034 method Methods 0.000 title claims abstract description 271
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 6
• 230000005764 inhibitory process Effects 0.000 title abstract description 6
• 230000008569 process Effects 0.000 title description 8
• 229940099797 HIV integrase inhibitor Drugs 0.000 title description 7
• 239000003084 hiv integrase inhibitor Substances 0.000 title description 7
• 201000010099 disease Diseases 0.000 title description 5
• 125000003118 aryl group Chemical group 0.000 claims abstract description 128
• 229940002612 prodrug Drugs 0.000 claims abstract description 104
• 239000000651 prodrug Substances 0.000 claims abstract description 104
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 71
• 125000001424 substituent group Chemical group 0.000 claims abstract description 34
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
• 108010002459 HIV Integrase Proteins 0.000 claims abstract description 15
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
• -1 cyclic lactam Chemical class 0.000 claims description 303
• UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical group [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 131
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 123
• 239000000203 mixture Substances 0.000 claims description 122
• 125000006239 protecting group Chemical group 0.000 claims description 117
• 150000002148 esters Chemical class 0.000 claims description 86
• 125000000217 alkyl group Chemical group 0.000 claims description 71
• 150000001412 amines Chemical class 0.000 claims description 63
• 230000015572 biosynthetic process Effects 0.000 claims description 59
• 229910052799 carbon Inorganic materials 0.000 claims description 52
• 229920006395 saturated elastomer Polymers 0.000 claims description 52
• 125000002947 alkylene group Chemical group 0.000 claims description 50
• 125000004122 cyclic group Chemical group 0.000 claims description 46
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 43
• 239000003153 chemical reaction reagent Substances 0.000 claims description 42
• 150000003839 salts Chemical class 0.000 claims description 37
• 229910019142 PO4 Inorganic materials 0.000 claims description 36
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical group [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 35
• 239000010452 phosphate Chemical group 0.000 claims description 35
• 125000003545 alkoxy group Chemical group 0.000 claims description 25
• 125000004432 carbon atom Chemical group C* 0.000 claims description 25
• 125000003282 alkyl amino group Chemical group 0.000 claims description 23
• 229910052794 bromium Inorganic materials 0.000 claims description 23
• 239000003795 chemical substances by application Substances 0.000 claims description 23
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 21
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 21
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
• IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 claims description 21
• 125000004450 alkenylene group Chemical group 0.000 claims description 20
• 125000004419 alkynylene group Chemical group 0.000 claims description 20
• 125000000623 heterocyclic group Chemical group 0.000 claims description 20
• 229910052740 iodine Inorganic materials 0.000 claims description 20
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 20
• 150000007942 carboxylates Chemical class 0.000 claims description 19
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 19
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 18
• 150000001356 alkyl thiols Chemical class 0.000 claims description 18
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
• 150000001350 alkyl halides Chemical class 0.000 claims description 15
• 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 14
• 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 14
• 150000008052 alkyl sulfonates Chemical class 0.000 claims description 14
• 239000003112 inhibitor Substances 0.000 claims description 14
• 229910052700 potassium Inorganic materials 0.000 claims description 14
• 125000004950 trifluoroalkyl group Chemical group 0.000 claims description 14
• 210000003819 peripheral blood mononuclear cell Anatomy 0.000 claims description 13
• KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 12
• 208000030507 AIDS Diseases 0.000 claims description 11
• 230000002401 inhibitory effect Effects 0.000 claims description 11
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
• 125000002619 bicyclic group Chemical group 0.000 claims description 10
• 150000003951 lactams Chemical class 0.000 claims description 8
• 229910052698 phosphorus Inorganic materials 0.000 claims description 8
• 229940124530 sulfonamide Drugs 0.000 claims description 8
• 150000003456 sulfonamides Chemical class 0.000 claims description 8
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
• 125000003368 amide group Chemical group 0.000 claims description 7
• 125000003107 substituted aryl group Chemical group 0.000 claims description 7
• 125000004665 trialkylsilyl group Chemical group 0.000 claims description 7
• BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 6
• 239000012453 solvate Substances 0.000 claims description 6
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
• UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 5
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
• 230000003834 intracellular effect Effects 0.000 claims description 5
• 239000002207 metabolite Substances 0.000 claims description 5
• 125000002950 monocyclic group Chemical group 0.000 claims description 5
• 150000003457 sulfones Chemical class 0.000 claims description 5
• 150000003462 sulfoxides Chemical class 0.000 claims description 5
• UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 5
• 208000031886 HIV Infections Diseases 0.000 claims description 4
• 125000005362 aryl sulfone group Chemical group 0.000 claims description 4
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
• 238000004891 communication Methods 0.000 claims description 4
• 150000002825 nitriles Chemical class 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
• 125000005208 trialkylammonium group Chemical group 0.000 claims description 4
• 241000124008 Mammalia Species 0.000 claims description 3
• 125000005360 alkyl sulfoxide group Chemical group 0.000 claims description 3
• 125000005361 aryl sulfoxide group Chemical group 0.000 claims description 3
• 125000005110 aryl thio group Chemical group 0.000 claims description 3
• ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 3
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 239000002955 immunomodulating agent Substances 0.000 claims description 3
• 229940121354 immunomodulator Drugs 0.000 claims description 3
• 210000000265 leukocyte Anatomy 0.000 claims description 3
• JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 claims description 2
• 208000037357 HIV infectious disease Diseases 0.000 claims description 2
• 229940122440 HIV protease inhibitor Drugs 0.000 claims description 2
• 229940122313 Nucleoside reverse transcriptase inhibitor Drugs 0.000 claims description 2
• 229960005475 antiinfective agent Drugs 0.000 claims description 2
• 239000004599 antimicrobial Substances 0.000 claims description 2
• 125000002837 carbocyclic group Chemical group 0.000 claims description 2
• 229910052731 fluorine Inorganic materials 0.000 claims description 2
• 239000004030 hiv protease inhibitor Substances 0.000 claims description 2
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 2
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 2
• 230000002584 immunomodulator Effects 0.000 claims description 2
• 230000003993 interaction Effects 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 claims description 2
• 239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 claims description 2
• 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims description 2
• 125000005189 alkyl hydroxy group Chemical group 0.000 claims 10
• 125000004849 alkoxymethyl group Chemical group 0.000 claims 2
• 239000003937 drug carrier Substances 0.000 claims 2
• DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 claims 1
• 102100031272 Calcineurin B homologous protein 2 Human genes 0.000 claims 1
• 241001510512 Chlamydia phage 2 Species 0.000 claims 1
• 101000777239 Homo sapiens Calcineurin B homologous protein 2 Proteins 0.000 claims 1
• 150000004703 alkoxides Chemical class 0.000 claims 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
• 150000002596 lactones Chemical class 0.000 claims 1
• 229940070891 pyridium Drugs 0.000 claims 1
• 239000000543 intermediate Substances 0.000 abstract description 38
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 17
• 239000001257 hydrogen Substances 0.000 abstract description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 4
• 150000002829 nitrogen Chemical class 0.000 abstract description 3
• 125000006413 ring segment Chemical group 0.000 abstract 1
• 239000000047 product Substances 0.000 description 199
• 238000006243 chemical reaction Methods 0.000 description 185
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 123
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 108
• 239000000243 solution Substances 0.000 description 107
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 96
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 86
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 84
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 81
• 238000005481 NMR spectroscopy Methods 0.000 description 59
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 57
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
• 239000002585 base Substances 0.000 description 50
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 49
• 238000002360 preparation method Methods 0.000 description 43
• 125000003710 aryl alkyl group Chemical group 0.000 description 36
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 34
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 34
• 239000007787 solid Substances 0.000 description 34
• 238000003786 synthesis reaction Methods 0.000 description 34
• 150000001408 amides Chemical class 0.000 description 33
• 150000005690 diesters Chemical class 0.000 description 33
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 31
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 31
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 30
• 239000011541 reaction mixture Substances 0.000 description 30
• 150000003008 phosphonic acid esters Chemical class 0.000 description 29
• 239000002253 acid Substances 0.000 description 28
• 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 28
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
• 229940059260 amidate Drugs 0.000 description 26
• 239000003814 drug Substances 0.000 description 26
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 25
• 239000002904 solvent Substances 0.000 description 25
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 24
• 239000000460 chlorine Substances 0.000 description 24
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
• 150000003009 phosphonic acids Chemical class 0.000 description 23
• 239000012044 organic layer Substances 0.000 description 21
• 125000002015 acyclic group Chemical group 0.000 description 20
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 20
• 229940079593 drug Drugs 0.000 description 20
• JRECPBYACBFQFW-UHFFFAOYSA-N 5h-quinoline-6,8-dione Chemical compound C1=CC=C2CC(=O)CC(=O)C2=N1 JRECPBYACBFQFW-UHFFFAOYSA-N 0.000 description 19
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
• 238000006460 hydrolysis reaction Methods 0.000 description 19
• 230000002829 reductive effect Effects 0.000 description 19
• 239000007858 starting material Substances 0.000 description 19
• 241000725303 Human immunodeficiency virus Species 0.000 description 18
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 18
• 230000007062 hydrolysis Effects 0.000 description 18
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 18
• 150000001721 carbon Chemical group 0.000 description 16
• 239000003054 catalyst Substances 0.000 description 16
• 210000004027 cell Anatomy 0.000 description 16
• 239000003480 eluent Substances 0.000 description 16
• 235000021317 phosphate Nutrition 0.000 description 16
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 15
• 150000001299 aldehydes Chemical class 0.000 description 15
• 239000012634 fragment Substances 0.000 description 15
• 125000004433 nitrogen atom Chemical group N* 0.000 description 15
• 229910000027 potassium carbonate Inorganic materials 0.000 description 15
• 125000004429 atom Chemical group 0.000 description 14
• 238000009472 formulation Methods 0.000 description 14
• 235000011181 potassium carbonates Nutrition 0.000 description 14
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 13
• 125000003342 alkenyl group Chemical group 0.000 description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 13
• NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 13
• 238000010992 reflux Methods 0.000 description 13
• 238000006467 substitution reaction Methods 0.000 description 13
• 238000004809 thin layer chromatography Methods 0.000 description 13
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• 239000012043 crude product Substances 0.000 description 12
• 125000000524 functional group Chemical group 0.000 description 12
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• 125000004185 ester group Chemical group 0.000 description 11
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
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• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
• 239000012299 nitrogen atmosphere Substances 0.000 description 11
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• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
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• 125000005997 bromomethyl group Chemical group 0.000 description 10
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• 125000005842 heteroatom Chemical group 0.000 description 10
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• 239000012442 inert solvent Substances 0.000 description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
• 229910052763 palladium Inorganic materials 0.000 description 10
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
• 238000000926 separation method Methods 0.000 description 10
• 150000003573 thiols Chemical class 0.000 description 10
• AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 10
• 101150072179 ATP1 gene Proteins 0.000 description 9
• 101100003366 Arabidopsis thaliana ATPA gene Proteins 0.000 description 9
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• 239000000969 carrier Substances 0.000 description 9
• 238000010511 deprotection reaction Methods 0.000 description 9
• 235000019439 ethyl acetate Nutrition 0.000 description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
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• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
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• QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 8
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
• 229960003767 alanine Drugs 0.000 description 8
• 235000004279 alanine Nutrition 0.000 description 8
• FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 8
• 239000003995 emulsifying agent Substances 0.000 description 8
• LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 8
• 125000004494 ethyl ester group Chemical group 0.000 description 8
• FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 8
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