HRP20041154A2 - SUBSTITUTED 3-AMINO-THIENO[2,3-b] PYRIDINE-2-CARBO - Google Patents

Info

Publication number

HRP20041154A2

HRP20041154A2 HR20041154A HRP20041154A HRP20041154A2 HR P20041154 A2 HRP20041154 A2 HR P20041154A2 HR 20041154 A HR20041154 A HR 20041154A HR P20041154 A HRP20041154 A HR P20041154A HR P20041154 A2 HRP20041154 A2 HR P20041154A2

Authority

HR

Croatia

Prior art keywords

amino

thieno

pyridine

6alkyl

piperidin

Prior art date

2002-06-06

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• -1 1-piperazinyl Chemical group 0.000 claims description 232
• 150000001875 compounds Chemical class 0.000 claims description 138
• 239000000203 mixture Substances 0.000 claims description 98
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 87
• 238000006243 chemical reaction Methods 0.000 claims description 80
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 63
• 125000000623 heterocyclic group Chemical group 0.000 claims description 59
• 125000004076 pyridyl group Chemical group 0.000 claims description 47
• 238000000034 method Methods 0.000 claims description 46
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 39
• 125000000217 alkyl group Chemical group 0.000 claims description 39
• 125000001072 heteroaryl group Chemical group 0.000 claims description 33
• 239000002904 solvent Substances 0.000 claims description 29
• 150000002148 esters Chemical class 0.000 claims description 27
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
• 150000003839 salts Chemical class 0.000 claims description 26
• 238000011282 treatment Methods 0.000 claims description 26
• 125000003386 piperidinyl group Chemical group 0.000 claims description 25
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 24
• 125000001544 thienyl group Chemical group 0.000 claims description 22
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 150000002367 halogens Chemical class 0.000 claims description 21
• 125000003545 alkoxy group Chemical group 0.000 claims description 20
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 19
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 18
• 125000002541 furyl group Chemical group 0.000 claims description 17
• 125000004193 piperazinyl group Chemical group 0.000 claims description 17
• 230000002757 inflammatory effect Effects 0.000 claims description 16
• 206010028980 Neoplasm Diseases 0.000 claims description 15
• 125000002883 imidazolyl group Chemical group 0.000 claims description 15
• 238000002360 preparation method Methods 0.000 claims description 15
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 14
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
• 125000002757 morpholinyl group Chemical group 0.000 claims description 14
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 14
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 13
• JUIKUQOUMZUFQT-UHFFFAOYSA-N 2-bromoacetamide Chemical compound NC(=O)CBr JUIKUQOUMZUFQT-UHFFFAOYSA-N 0.000 claims description 12
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 11
• NFKLVUJJLJOREJ-UHFFFAOYSA-N 3-amino-6-(4-hydroxypiperidin-1-yl)thieno[2,3-b]pyridine-2,4-dicarboxylic acid Chemical compound C=1C(C(O)=O)=C2C(N)=C(C(O)=O)SC2=NC=1N1CCC(O)CC1 NFKLVUJJLJOREJ-UHFFFAOYSA-N 0.000 claims description 11
• 229910006074 SO2NH2 Inorganic materials 0.000 claims description 11
• 229910052731 fluorine Inorganic materials 0.000 claims description 11
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 10
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 10
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 230000001363 autoimmune Effects 0.000 claims description 8
• 125000003725 azepanyl group Chemical group 0.000 claims description 8
• 201000011510 cancer Diseases 0.000 claims 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 claims description 8
• 208000023275 Autoimmune disease Diseases 0.000 claims description 7
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 6
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 6
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 6
• 230000001154 acute effect Effects 0.000 claims description 6
• 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 6
• 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 6
• 208000027866 inflammatory disease Diseases 0.000 claims description 6
• 150000004702 methyl esters Chemical class 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
• 208000035475 disorder Diseases 0.000 claims description 5
• 125000001041 indolyl group Chemical group 0.000 claims description 5
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
• 125000005983 2,5-diazabicyclo[2.2.1]heptan-2-yl group Chemical group 0.000 claims description 4
• MTIAEVDFLNZWBL-UHFFFAOYSA-N 3-amino-6-(4-amino-4-cyanopiperidin-1-yl)-4-propylthieno[2,3-b]pyridine-2-carboxamide Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(CCC)=CC=1N1CCC(N)(C#N)CC1 MTIAEVDFLNZWBL-UHFFFAOYSA-N 0.000 claims description 4
• BZNUHRDIJQWTTQ-UHFFFAOYSA-N 3-amino-6-(4-aminopiperidin-1-yl)-4-(4-nitrophenyl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1CC(N)CCN1C1=CC(C=2C=CC(=CC=2)[N+]([O-])=O)=C(C(N)=C(S2)C(N)=O)C2=N1 BZNUHRDIJQWTTQ-UHFFFAOYSA-N 0.000 claims description 4
• JLBBNBJDNWXYBL-VOTSOKGWSA-N 3-amino-6-(4-aminopiperidin-1-yl)-4-[(e)-2-phenylethenyl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1CC(N)CCN1C1=CC(\C=C\C=2C=CC=CC=2)=C(C(N)=C(S2)C(N)=O)C2=N1 JLBBNBJDNWXYBL-VOTSOKGWSA-N 0.000 claims description 4
• OYWOGJOEDCLNEU-UHFFFAOYSA-N 3-amino-6-(4-oxopiperidin-1-yl)-4-propylthieno[2,3-b]pyridine-2-carboxamide Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(CCC)=CC=1N1CCC(=O)CC1 OYWOGJOEDCLNEU-UHFFFAOYSA-N 0.000 claims description 4
• DMJAFCNEDMCMCG-NSHDSACASA-N 3-amino-6-[4-[[(2s)-2-hydroxypropyl]amino]piperidin-1-yl]-4-propylthieno[2,3-b]pyridine-2-carboxamide Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(CCC)=CC=1N1CCC(NC[C@H](C)O)CC1 DMJAFCNEDMCMCG-NSHDSACASA-N 0.000 claims description 4
• 208000026310 Breast neoplasm Diseases 0.000 claims description 4
• 208000002193 Pain Diseases 0.000 claims description 4
• 125000004414 alkyl thio group Chemical group 0.000 claims description 4
• 208000006673 asthma Diseases 0.000 claims description 4
• 208000014674 injury Diseases 0.000 claims description 4
• 125000005961 oxazepanyl group Chemical group 0.000 claims description 4
• 125000005505 thiomorpholino group Chemical group 0.000 claims description 4
• KHBYHZRMMMNCRG-UHFFFAOYSA-N 3-amino-4-ethoxy-6-(4-hydroxypiperidin-1-yl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(OCC)=CC=1N1CCC(O)CC1 KHBYHZRMMMNCRG-UHFFFAOYSA-N 0.000 claims description 3
• BVVKINYXDIJKIT-UHFFFAOYSA-N 3-amino-6-(4-amino-4-methylpiperidin-1-yl)-4-ethoxythieno[2,3-b]pyridine-2-carboxamide Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(OCC)=CC=1N1CCC(C)(N)CC1 BVVKINYXDIJKIT-UHFFFAOYSA-N 0.000 claims description 3
• NEEKCMNGBAHAMC-UHFFFAOYSA-N 3-amino-6-(4-aminopiperidin-1-yl)-4-ethoxythieno[2,3-b]pyridine-2-carboxamide Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(OCC)=CC=1N1CCC(N)CC1 NEEKCMNGBAHAMC-UHFFFAOYSA-N 0.000 claims description 3
• LYXUMHUYBOQJLB-UHFFFAOYSA-N 3-amino-6-(4-aminopiperidin-1-yl)-4-methylsulfanylthieno[2,3-b]pyridine-2-carboxamide Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(SC)=CC=1N1CCC(N)CC1 LYXUMHUYBOQJLB-UHFFFAOYSA-N 0.000 claims description 3
• IADACRYWVHWRLA-UHFFFAOYSA-N 3-amino-6-(4-aminopiperidin-1-yl)-4-propan-2-yloxythieno[2,3-b]pyridine-2-carboxamide Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(OC(C)C)=CC=1N1CCC(N)CC1 IADACRYWVHWRLA-UHFFFAOYSA-N 0.000 claims description 3
• GGXPEWPWJNSCPI-UHFFFAOYSA-N 3-amino-6-(4-hydroxypiperidin-1-yl)-4-(3-hydroxypropyl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=1C(CCCO)=C2C(N)=C(C(=O)N)SC2=NC=1N1CCC(O)CC1 GGXPEWPWJNSCPI-UHFFFAOYSA-N 0.000 claims description 3
• NSUOUCFIOXVTFA-UHFFFAOYSA-N 3-amino-6-piperazin-1-yl-4-(trifluoromethyl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=1C(C(F)(F)F)=C2C(N)=C(C(=O)N)SC2=NC=1N1CCNCC1 NSUOUCFIOXVTFA-UHFFFAOYSA-N 0.000 claims description 3
• 206010006187 Breast cancer Diseases 0.000 claims description 3
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
• 206010025323 Lymphomas Diseases 0.000 claims description 3
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
• 239000003153 chemical reaction reagent Substances 0.000 claims description 3
• 230000006378 damage Effects 0.000 claims description 3
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 3
• 208000032839 leukemia Diseases 0.000 claims description 3
• 230000036210 malignancy Effects 0.000 claims description 3
• 208000010125 myocardial infarction Diseases 0.000 claims description 3
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 201000008482 osteoarthritis Diseases 0.000 claims description 3
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
• VXIVSQZSERGHQP-HQMMCQRPSA-N 2-chloroacetamide Chemical group N[14C](=O)CCl VXIVSQZSERGHQP-HQMMCQRPSA-N 0.000 claims description 2
• ALEHIGVCNCPFJF-UHFFFAOYSA-N 3-amino-4-(4-cyano-3-fluorophenyl)-6-(4-hydroxypiperidin-1-yl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C=12C(N)=C(C(=O)N)SC2=NC(N2CCC(O)CC2)=CC=1C1=CC=C(C#N)C(F)=C1 ALEHIGVCNCPFJF-UHFFFAOYSA-N 0.000 claims description 2
• NYRHABRBHITKBD-UHFFFAOYSA-N 3-amino-6-(1h-indol-3-ylmethylamino)-4-propylthieno[2,3-b]pyridine-2-carboxamide Chemical compound C1=CC=C2C(CNC=3C=C(C=4C(N)=C(C(N)=O)SC=4N=3)CCC)=CNC2=C1 NYRHABRBHITKBD-UHFFFAOYSA-N 0.000 claims description 2
• RWSSJVJKPTXJQL-UHFFFAOYSA-N 3-amino-6-(4-amino-3,3-dimethylcyclohexyl)-4-propylthieno[2,3-b]pyridine-2-carboxamide Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(CCC)=CC=1C1CCC(N)C(C)(C)C1 RWSSJVJKPTXJQL-UHFFFAOYSA-N 0.000 claims description 2
• GMYKFOPFZNINQR-UHFFFAOYSA-N 3-amino-6-(4-amino-3-hydroxypiperidin-1-yl)-4-propylthieno[2,3-b]pyridine-2-carboxamide Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(CCC)=CC=1N1CCC(N)C(O)C1 GMYKFOPFZNINQR-UHFFFAOYSA-N 0.000 claims description 2
• KDDWRPRQCHBICJ-UHFFFAOYSA-N 3-amino-6-(4-aminoazepan-1-yl)-4-propylthieno[2,3-b]pyridine-2-carboxamide Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(CCC)=CC=1N1CCCC(N)CC1 KDDWRPRQCHBICJ-UHFFFAOYSA-N 0.000 claims description 2
• DDXLMQIWDFWTFE-UHFFFAOYSA-N 3-amino-6-(4-aminopiperidin-1-yl)-4-(2,4-difluorophenyl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1CC(N)CCN1C1=CC(C=2C(=CC(F)=CC=2)F)=C(C(N)=C(S2)C(N)=O)C2=N1 DDXLMQIWDFWTFE-UHFFFAOYSA-N 0.000 claims description 2
• LKBQVRWZCUFPRC-UHFFFAOYSA-N 3-amino-6-(4-aminopiperidin-1-yl)-4-(2,5-difluorophenyl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1CC(N)CCN1C1=CC(C=2C(=CC=C(F)C=2)F)=C(C(N)=C(S2)C(N)=O)C2=N1 LKBQVRWZCUFPRC-UHFFFAOYSA-N 0.000 claims description 2
• FPBFUNNLBPPXDL-UHFFFAOYSA-N 3-amino-6-(4-aminopiperidin-1-yl)-4-(4-cyano-3-fluorophenyl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1CC(N)CCN1C1=CC(C=2C=C(F)C(C#N)=CC=2)=C(C(N)=C(S2)C(N)=O)C2=N1 FPBFUNNLBPPXDL-UHFFFAOYSA-N 0.000 claims description 2
• PMEHDKFOFXOLRY-VOTSOKGWSA-N 3-amino-6-(4-aminopiperidin-1-yl)-4-[(e)-2-(4-methylphenyl)ethenyl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1=CC(C)=CC=C1\C=C\C1=CC(N2CCC(N)CC2)=NC2=C1C(N)=C(C(N)=O)S2 PMEHDKFOFXOLRY-VOTSOKGWSA-N 0.000 claims description 2
• SFRFRKNOPPYTOS-UHFFFAOYSA-N 3-amino-6-(4-hydroxypiperidin-1-yl)-4-(4-methylsulfonylphenyl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(N2CCC(O)CC2)=NC2=C1C(N)=C(C(N)=O)S2 SFRFRKNOPPYTOS-UHFFFAOYSA-N 0.000 claims description 2
• FGNMZEZEQQMLDQ-UHFFFAOYSA-N 3-amino-6-[2-(aminomethyl)piperidin-1-yl]-4-propylthieno[2,3-b]pyridine-2-carboxamide Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(CCC)=CC=1N1CCCCC1CN FGNMZEZEQQMLDQ-UHFFFAOYSA-N 0.000 claims description 2
• ROKNIKLGTCUQSG-UHFFFAOYSA-N 3-amino-6-[4-(2-hydroxyethylamino)piperidin-1-yl]-4-propylthieno[2,3-b]pyridine-2-carboxamide Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(CCC)=CC=1N1CCC(NCCO)CC1 ROKNIKLGTCUQSG-UHFFFAOYSA-N 0.000 claims description 2
• UAAXDGAQLNVGJU-UHFFFAOYSA-N 3-amino-6-[4-(anilinocarbamoyl)piperazin-1-yl]-4-propylthieno[2,3-b]pyridine-2-carboxamide Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(CCC)=CC=1N(CC1)CCN1C(=O)NNC1=CC=CC=C1 UAAXDGAQLNVGJU-UHFFFAOYSA-N 0.000 claims description 2
• IXXUOEYLTTUTOD-UHFFFAOYSA-N 3-amino-6-[4-(carbamoylamino)piperidin-1-yl]-4-propylthieno[2,3-b]pyridine-2-carboxamide Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(CCC)=CC=1N1CCC(NC(N)=O)CC1 IXXUOEYLTTUTOD-UHFFFAOYSA-N 0.000 claims description 2
• CREAHTMWKXOTPH-UHFFFAOYSA-N 3-amino-6-[4-(methanesulfonamido)piperidin-1-yl]-4-propylthieno[2,3-b]pyridine-2-carboxamide Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(CCC)=CC=1N1CCC(NS(C)(=O)=O)CC1 CREAHTMWKXOTPH-UHFFFAOYSA-N 0.000 claims description 2
• ZAAYLLURXCAEMP-UHFFFAOYSA-N 3-amino-6-[4-[(2-hydroxy-2-phenylethyl)amino]piperidin-1-yl]-4-propylthieno[2,3-b]pyridine-2-carboxamide Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(CCC)=CC=1N(CC1)CCC1NCC(O)C1=CC=CC=C1 ZAAYLLURXCAEMP-UHFFFAOYSA-N 0.000 claims description 2
• UMLYAHRGHSFGGN-UHFFFAOYSA-N 3-amino-6-piperidin-4-yl-4-propylthieno[2,3-b]pyridine-2-carboxamide Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(CCC)=CC=1C1CCNCC1 UMLYAHRGHSFGGN-UHFFFAOYSA-N 0.000 claims description 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• SZTTUBLYHXHAML-UHFFFAOYSA-N 4-[2-[[1-(3-amino-2-carbamoyl-4-propylthieno[2,3-b]pyridin-6-yl)piperidin-4-yl]amino]-1-hydroxyethyl]benzoic acid Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(CCC)=CC=1N(CC1)CCC1NCC(O)C1=CC=C(C(O)=O)C=C1 SZTTUBLYHXHAML-UHFFFAOYSA-N 0.000 claims description 2
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
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• LBVMBECAHIBYAO-UHFFFAOYSA-N methyl 4-[3-amino-6-(4-aminopiperidin-1-yl)-2-carbamoylthieno[2,3-b]pyridin-4-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC(N2CCC(N)CC2)=NC2=C1C(N)=C(C(N)=O)S2 LBVMBECAHIBYAO-UHFFFAOYSA-N 0.000 claims description 2
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• 125000006187 phenyl benzyl group Chemical group 0.000 claims description 2
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• SLZQVXKKOAEGCQ-UHFFFAOYSA-N 3-amino-6-(4-aminopiperidin-1-yl)-4-(4-methylsulfonylphenyl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(N2CCC(N)CC2)=NC2=C1C(N)=C(C(N)=O)S2 SLZQVXKKOAEGCQ-UHFFFAOYSA-N 0.000 claims 1
• LZBBYYQKWSFFRD-UHFFFAOYSA-N 3-amino-6-(4-hydroxycyclohexyl)thieno[2,3-b]pyridine-2,4-dicarboxylic acid Chemical compound C=1C(C(O)=O)=C2C(N)=C(C(O)=O)SC2=NC=1C1CCC(O)CC1 LZBBYYQKWSFFRD-UHFFFAOYSA-N 0.000 claims 1
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• YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
• 125000000169 tricyclic heterocycle group Chemical group 0.000 description 1
• LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
• IHIXIJGXTJIKRB-UHFFFAOYSA-N trisodium vanadate Chemical compound [Na+].[Na+].[Na+].[O-][V]([O-])([O-])=O IHIXIJGXTJIKRB-UHFFFAOYSA-N 0.000 description 1
• 238000011144 upstream manufacturing Methods 0.000 description 1
• AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical class N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 description 1