TWI334417B - Azaindoles - Google Patents

Info

Publication number

TWI334417B

TWI334417B TW091113956A TW91113956A TWI334417B TW I334417 B TWI334417 B TW I334417B TW 091113956 A TW091113956 A TW 091113956A TW 91113956 A TW91113956 A TW 91113956A TW I334417 B TWI334417 B TW I334417B

Authority

TW

Taiwan

Prior art keywords

pyrrolo

pyridin

group

indol

methyl

Prior art date

2001-06-21

Links

• Espacenet
• Global Dossier
• Discuss

• 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 title description 7
• 150000001875 compounds Chemical class 0.000 claims description 587
• -1 aryl ketone Chemical class 0.000 claims description 258
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 252
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 239
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 225
• 125000000217 alkyl group Chemical group 0.000 claims description 186
• 239000002253 acid Substances 0.000 claims description 96
• 229910052739 hydrogen Inorganic materials 0.000 claims description 91
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 90
• 239000001257 hydrogen Substances 0.000 claims description 87
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 87
• 150000003839 salts Chemical class 0.000 claims description 78
• 125000003118 aryl group Chemical group 0.000 claims description 66
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 66
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 65
• 238000007639 printing Methods 0.000 claims description 62
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 61
• 230000002079 cooperative effect Effects 0.000 claims description 60
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 55
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 54
• 125000003545 alkoxy group Chemical group 0.000 claims description 52
• 150000001412 amines Chemical class 0.000 claims description 40
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 40
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 40
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 39
• TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Natural products OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims description 39
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 37
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
• MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 35
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 35
• 229910052799 carbon Inorganic materials 0.000 claims description 33
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 31
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 31
• 239000007789 gas Substances 0.000 claims description 31
• MVXVYAKCVDQRLW-UHFFFAOYSA-N azain Natural products C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 claims description 30
• 125000004076 pyridyl group Chemical group 0.000 claims description 30
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 26
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 25
• 239000000460 chlorine Substances 0.000 claims description 25
• WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 24
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
• 125000003277 amino group Chemical group 0.000 claims description 23
• 235000019260 propionic acid Nutrition 0.000 claims description 23
• 125000005843 halogen group Chemical group 0.000 claims description 22
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 21
• BHHMPZQRVWVAAR-UHFFFAOYSA-N 7-bromo-8-methylpyrido[2,3-b]pyrazine Chemical compound C1=CN=C2C(C)=C(Br)C=NC2=N1 BHHMPZQRVWVAAR-UHFFFAOYSA-N 0.000 claims description 20
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 19
• QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 18
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• 229960004063 propylene glycol Drugs 0.000 claims description 17
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 16
• DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 16
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 16
• 239000004146 Propane-1,2-diol Substances 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 14
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 14
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 13
• 238000003971 tillage Methods 0.000 claims description 13
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 12
• 150000002923 oximes Chemical class 0.000 claims description 12
• 150000002148 esters Chemical class 0.000 claims description 11
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 11
• IKVDMBQGHZVMRN-UHFFFAOYSA-N n-methyldecan-1-amine Chemical compound CCCCCCCCCCNC IKVDMBQGHZVMRN-UHFFFAOYSA-N 0.000 claims description 10
• FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 10
• IACBQUVFVZBFQO-UHFFFAOYSA-N 2-(decylamino)-2-methylpropan-1-ol Chemical compound CCCCCCCCCCNC(C)(C)CO IACBQUVFVZBFQO-UHFFFAOYSA-N 0.000 claims description 9
• HFTVJMFWJUFBNO-UHFFFAOYSA-N 5h-pyrrolo[2,3-b]pyrazine Chemical compound C1=CN=C2NC=CC2=N1 HFTVJMFWJUFBNO-UHFFFAOYSA-N 0.000 claims description 9
• 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 9
• PJNIZPXBKOEEGD-UHFFFAOYSA-N 2-(decylamino)ethanol Chemical compound CCCCCCCCCCNCCO PJNIZPXBKOEEGD-UHFFFAOYSA-N 0.000 claims description 8
• OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 8
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 8
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 8
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 8
• 150000002576 ketones Chemical class 0.000 claims description 8
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
• 239000000052 vinegar Substances 0.000 claims description 8
• 235000021419 vinegar Nutrition 0.000 claims description 8
• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 7
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 125000001475 halogen functional group Chemical group 0.000 claims description 7
• DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 7
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 7
• VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 6
• ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 claims description 6
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 6
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 150000002431 hydrogen Chemical group 0.000 claims description 6
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
• GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 claims description 6
• ASSOHGIOBRRHCW-UHFFFAOYSA-N 1-(decylamino)propan-2-ol Chemical compound CCCCCCCCCCNCC(C)O ASSOHGIOBRRHCW-UHFFFAOYSA-N 0.000 claims description 5
• 125000004414 alkyl thio group Chemical group 0.000 claims description 5
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
• 229910052707 ruthenium Inorganic materials 0.000 claims description 5
• XBDYBAVJXHJMNQ-UHFFFAOYSA-N 1,2,3,4-tetrahydroanthracene Chemical compound C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 claims description 4
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 4
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
• 229930182558 Sterol Natural products 0.000 claims description 4
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 235000003702 sterols Nutrition 0.000 claims description 4
• KELLLGDNFSNCIO-UHFFFAOYSA-N 2-(2-phenyl-1h-pyrrolo[2,3-b]pyridin-3-yl)acetonitrile Chemical compound N1C2=NC=CC=C2C(CC#N)=C1C1=CC=CC=C1 KELLLGDNFSNCIO-UHFFFAOYSA-N 0.000 claims description 3
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
• UIEJEXBQVZLMGC-UHFFFAOYSA-N 3-(decylamino)propane-1,2-diol Chemical compound CCCCCCCCCCNCC(O)CO UIEJEXBQVZLMGC-UHFFFAOYSA-N 0.000 claims description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• SOOQWPVTSIZPTI-UHFFFAOYSA-N 6-indol-1-yl-5h-pyrrolo[2,3-b]pyrazine Chemical compound C1=CN=C2NC(N3C4=CC=CC=C4C=C3)=CC2=N1 SOOQWPVTSIZPTI-UHFFFAOYSA-N 0.000 claims description 3
• UCDBLYHPJMMFMY-UHFFFAOYSA-N 8-bromoquinoline-4-carbonitrile Chemical compound C1=CN=C2C(Br)=CC=CC2=C1C#N UCDBLYHPJMMFMY-UHFFFAOYSA-N 0.000 claims description 3
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 3
• VAJKPVXZQQVHFN-UHFFFAOYSA-N OC(CNCCCCCCCCCC)(C)S Chemical compound OC(CNCCCCCCCCCC)(C)S VAJKPVXZQQVHFN-UHFFFAOYSA-N 0.000 claims description 3
• PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 3
• 125000001246 bromo group Chemical group Br* 0.000 claims description 3
• 239000004202 carbamide Substances 0.000 claims description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
• TWBYWOBDOCUKOW-UHFFFAOYSA-M isonicotinate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 claims description 3
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 3
• 229960005181 morphine Drugs 0.000 claims description 3
• 150000002825 nitriles Chemical class 0.000 claims description 3
• FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 3
• 229940124530 sulfonamide Drugs 0.000 claims description 3
• VFIDFFAQOVMDBB-UHFFFAOYSA-N 2-[3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]ethanol Chemical compound C12=CC=CC=C2N(CCO)C=C1C1=CC2=NC=CN=C2N1 VFIDFFAQOVMDBB-UHFFFAOYSA-N 0.000 claims description 2
• OGCFKNMRJGBFPU-UHFFFAOYSA-N 2-phenyl-3-prop-1-enyl-1h-pyrrolo[2,3-b]pyridine Chemical compound N1C2=NC=CC=C2C(C=CC)=C1C1=CC=CC=C1 OGCFKNMRJGBFPU-UHFFFAOYSA-N 0.000 claims description 2
• ALSYTSCUTDAYIU-UHFFFAOYSA-N 2-pyridin-3-yl-1h-pyrrolo[2,3-b]pyridine Chemical compound N1C2=NC=CC=C2C=C1C1=CC=CN=C1 ALSYTSCUTDAYIU-UHFFFAOYSA-N 0.000 claims description 2
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• JTVAIENGRBHJPO-UHFFFAOYSA-N 3-(decylamino)propan-1-ol Chemical compound CCCCCCCCCCNCCCO JTVAIENGRBHJPO-UHFFFAOYSA-N 0.000 claims description 2
• CNJGCQXKBAUFNA-UHFFFAOYSA-N 4-(3-methyl-1h-pyrrolo[2,3-b]pyridin-2-yl)benzoic acid Chemical compound N1C2=NC=CC=C2C(C)=C1C1=CC=C(C(O)=O)C=C1 CNJGCQXKBAUFNA-UHFFFAOYSA-N 0.000 claims description 2
• CVACBBRVBUGFQO-UHFFFAOYSA-N 6-(1h-indol-2-yl)-5h-pyrrolo[2,3-b]pyrazine Chemical compound C1=CN=C2NC(C3=CC4=CC=CC=C4N3)=CC2=N1 CVACBBRVBUGFQO-UHFFFAOYSA-N 0.000 claims description 2
• ONJMAXYFHBVNTH-UHFFFAOYSA-N 6-phenyl-5h-pyrrolo[2,3-b]pyrazine Chemical compound N1C2=NC=CN=C2C=C1C1=CC=CC=C1 ONJMAXYFHBVNTH-UHFFFAOYSA-N 0.000 claims description 2
• LVARNOHOOZOAGQ-UHFFFAOYSA-N 6-phenyl-7-propan-2-yl-5h-pyrrolo[2,3-b]pyrazine Chemical compound N1C2=NC=CN=C2C(C(C)C)=C1C1=CC=CC=C1 LVARNOHOOZOAGQ-UHFFFAOYSA-N 0.000 claims description 2
• 241000989913 Gunnera petaloidea Species 0.000 claims description 2
• MXROJUHFNKBVPW-UHFFFAOYSA-N N-(2-fluoroethyl)decan-1-amine Chemical compound CCCCCCCCCCNCCF MXROJUHFNKBVPW-UHFFFAOYSA-N 0.000 claims description 2
• 150000001408 amides Chemical class 0.000 claims description 2
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
• 125000005577 anthracene group Chemical group 0.000 claims description 2
• 229910052801 chlorine Inorganic materials 0.000 claims description 2
• 230000000052 comparative effect Effects 0.000 claims description 2
• 235000011187 glycerol Nutrition 0.000 claims description 2
• 125000002883 imidazolyl group Chemical group 0.000 claims description 2
• 125000000468 ketone group Chemical group 0.000 claims description 2
• 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
• 150000002602 lanthanoids Chemical class 0.000 claims description 2
• 239000000463 material Substances 0.000 claims description 2
• 150000004702 methyl esters Chemical class 0.000 claims description 2
• FILUFGAZMJGNEN-UHFFFAOYSA-N pent-1-en-3-yne Chemical group CC#CC=C FILUFGAZMJGNEN-UHFFFAOYSA-N 0.000 claims description 2
• ZXAPIQZSJHLLDS-UHFFFAOYSA-N tert-butyl pyridine-4-carboxylate Chemical compound CC(C)(C)OC(=O)C1=CC=NC=C1 ZXAPIQZSJHLLDS-UHFFFAOYSA-N 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 23
• 125000000000 cycloalkoxy group Chemical group 0.000 claims 13
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 12
• 125000003282 alkyl amino group Chemical group 0.000 claims 11
• 239000010949 copper Substances 0.000 claims 11
• 239000007983 Tris buffer Substances 0.000 claims 4
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 4
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims 4
• 125000005907 alkyl ester group Chemical group 0.000 claims 4
• TWBYWOBDOCUKOW-ZQBYOMGUSA-N pyridine-4-carboxylic acid Chemical compound O[14C](=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-ZQBYOMGUSA-N 0.000 claims 4
• PHYLEHPTWGIEHS-UHFFFAOYSA-N C(CCCCCCCCC)OCCNCCCCCCCCCC Chemical compound C(CCCCCCCCC)OCCNCCCCCCCCCC PHYLEHPTWGIEHS-UHFFFAOYSA-N 0.000 claims 3
• LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 claims 3
• 150000003573 thiols Chemical class 0.000 claims 3
• VUTBELPREDJDDH-UHFFFAOYSA-N 4-amino-5-hydroxymethyl-2-methylpyrimidine Chemical compound CC1=NC=C(CO)C(N)=N1 VUTBELPREDJDDH-UHFFFAOYSA-N 0.000 claims 2
• PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims 2
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
• 125000002757 morpholinyl group Chemical group 0.000 claims 2
• 235000008160 pyridoxine Nutrition 0.000 claims 2
• 239000011677 pyridoxine Substances 0.000 claims 2
• 125000005554 pyridyloxy group Chemical group 0.000 claims 2
• 239000011347 resin Substances 0.000 claims 2
• 229920005989 resin Polymers 0.000 claims 2
• PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims 2
• 235000021286 stilbenes Nutrition 0.000 claims 2
• 229940011671 vitamin b6 Drugs 0.000 claims 2
• IDFPQEHZYBXIFO-GFCCVEGCSA-N (R)-(4-fluoro-2-propylphenyl)-(1H-imidazol-2-yl)methanol Chemical compound CCCc1cc(F)ccc1[C@@H](O)c1ncc[nH]1 IDFPQEHZYBXIFO-GFCCVEGCSA-N 0.000 claims 1
• QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 1
• BNRANURXPKRRKP-UHFFFAOYSA-N 1-[tert-butyl-[(4-methylphenyl)methyl]amino]-3-(1H-indol-4-yloxy)propan-2-ol Chemical compound Cc1ccc(CN(CC(O)COc2cccc3[nH]ccc23)C(C)(C)C)cc1 BNRANURXPKRRKP-UHFFFAOYSA-N 0.000 claims 1
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