CA2486061A1 - Using a selective inos inhibitor for the treatment of respiratory diseases and conditions - Google Patents

Info

Publication number

CA2486061A1

CA2486061A1 CA002486061A CA2486061A CA2486061A1 CA 2486061 A1 CA2486061 A1 CA 2486061A1 CA 002486061 A CA002486061 A CA 002486061A CA 2486061 A CA2486061 A CA 2486061A CA 2486061 A1 CA2486061 A1 CA 2486061A1

Authority

CA

Canada

Prior art keywords

alkyl

optionally substituted

group

amino

halo

Prior art date

2002-05-16

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
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• 208000023504 respiratory system disease Diseases 0.000 title claims abstract description 22
• 238000011282 treatment Methods 0.000 title claims abstract description 19
• 239000003112 inhibitor Substances 0.000 title description 38
• 101100396994 Drosophila melanogaster Inos gene Proteins 0.000 title 1
• 238000000034 method Methods 0.000 claims abstract description 93
• 229940124639 Selective inhibitor Drugs 0.000 claims abstract description 10
• 108010076864 Nitric Oxide Synthase Type II Proteins 0.000 claims abstract description 9
• 102000011779 Nitric Oxide Synthase Type II Human genes 0.000 claims abstract description 9
• 230000002265 prevention Effects 0.000 claims abstract description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 216
• 125000005843 halogen group Chemical group 0.000 claims description 151
• -1 heteroaralkoxy Chemical group 0.000 claims description 144
• 125000003545 alkoxy group Chemical group 0.000 claims description 135
• 238000006243 chemical reaction Methods 0.000 claims description 106
• 229910052739 hydrogen Inorganic materials 0.000 claims description 101
• 150000001875 compounds Chemical class 0.000 claims description 86
• 239000001257 hydrogen Substances 0.000 claims description 76
• 208000006673 asthma Diseases 0.000 claims description 75
• 150000002431 hydrogen Chemical group 0.000 claims description 65
• 125000000623 heterocyclic group Chemical group 0.000 claims description 59
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 57
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 57
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 53
• 229910052757 nitrogen Inorganic materials 0.000 claims description 50
• 150000003839 salts Chemical class 0.000 claims description 50
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 36
• 125000003118 aryl group Chemical group 0.000 claims description 34
• 206010006451 bronchitis Diseases 0.000 claims description 29
• 229910052799 carbon Inorganic materials 0.000 claims description 28
• 125000001072 heteroaryl group Chemical group 0.000 claims description 26
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
• 229940119568 Inducible nitric oxide synthase inhibitor Drugs 0.000 claims description 23
• 125000003107 substituted aryl group Chemical group 0.000 claims description 23
• 125000001188 haloalkyl group Chemical group 0.000 claims description 22
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 21
• 125000001424 substituent group Chemical group 0.000 claims description 19
• 125000000304 alkynyl group Chemical group 0.000 claims description 17
• 125000004429 atom Chemical group 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 150000002367 halogens Chemical class 0.000 claims description 16
• 206010006458 Bronchitis chronic Diseases 0.000 claims description 15
• 206010061218 Inflammation Diseases 0.000 claims description 15
• 239000004201 L-cysteine Substances 0.000 claims description 15
• 208000007451 chronic bronchitis Diseases 0.000 claims description 15
• 230000004054 inflammatory process Effects 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 15
• 230000000241 respiratory effect Effects 0.000 claims description 15
• 125000003342 alkenyl group Chemical group 0.000 claims description 13
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
• 125000005842 heteroatom Chemical group 0.000 claims description 13
• 210000004072 lung Anatomy 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 12
• 201000010099 disease Diseases 0.000 claims description 12
• 230000005764 inhibitory process Effects 0.000 claims description 12
• 229910052717 sulfur Inorganic materials 0.000 claims description 12
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
• 206010014561 Emphysema Diseases 0.000 claims description 10
• 125000004414 alkyl thio group Chemical group 0.000 claims description 10
• 230000001684 chronic effect Effects 0.000 claims description 10
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
• 230000001154 acute effect Effects 0.000 claims description 9
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
• 125000004442 acylamino group Chemical group 0.000 claims description 8
• 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 8
• 239000013566 allergen Substances 0.000 claims description 8
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 8
• 125000004104 aryloxy group Chemical group 0.000 claims description 8
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• CUGZEDSDRBMZMY-UHFFFAOYSA-N trihydrate;hydrochloride Chemical compound O.O.O.Cl CUGZEDSDRBMZMY-UHFFFAOYSA-N 0.000 claims description 8
• 230000003612 virological effect Effects 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 239000001301 oxygen Substances 0.000 claims description 7
• VQGCWTDMOOOHCH-PFPYCLJUSA-N (z,2s)-2-amino-7-(1-aminoethylideneamino)-6-fluorohept-5-enoic acid Chemical compound CC(=N)NC\C(F)=C\CC[C@H](N)C(O)=O VQGCWTDMOOOHCH-PFPYCLJUSA-N 0.000 claims description 6
• 206010003557 Asthma exercise induced Diseases 0.000 claims description 6
• 208000004657 Exercise-Induced Asthma Diseases 0.000 claims description 6
• 208000024695 exercise-induced bronchoconstriction Diseases 0.000 claims description 6
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
• 150000004682 monohydrates Chemical class 0.000 claims description 6
• VQGCWTDMOOOHCH-DKCNVOGISA-N (e,2s)-2-amino-7-(1-aminoethylideneamino)-6-fluorohept-5-enoic acid Chemical compound CC(=N)NC\C(F)=C/CC[C@H](N)C(O)=O VQGCWTDMOOOHCH-DKCNVOGISA-N 0.000 claims description 5
• 206010003504 Aspiration Diseases 0.000 claims description 5
• 206010035664 Pneumonia Diseases 0.000 claims description 5
• 206010040047 Sepsis Diseases 0.000 claims description 5
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
• 208000010444 Acidosis Diseases 0.000 claims description 4
• 206010001029 Acute pulmonary oedema Diseases 0.000 claims description 4
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 4
• 208000035939 Alveolitis allergic Diseases 0.000 claims description 4
• 241000272201 Columbiformes Species 0.000 claims description 4
• 201000003883 Cystic fibrosis Diseases 0.000 claims description 4
• 208000027445 Farmer Lung Diseases 0.000 claims description 4
• 208000003241 Fat Embolism Diseases 0.000 claims description 4
• 208000000203 Hyaline Membrane Disease Diseases 0.000 claims description 4
• 206010021143 Hypoxia Diseases 0.000 claims description 4
• 208000032571 Infant acute respiratory distress syndrome Diseases 0.000 claims description 4
• 208000034388 Mountain sickness acute Diseases 0.000 claims description 4
• 206010028974 Neonatal respiratory distress syndrome Diseases 0.000 claims description 4
• 208000010378 Pulmonary Embolism Diseases 0.000 claims description 4
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
• 208000027418 Wounds and injury Diseases 0.000 claims description 4
• 230000007950 acidosis Effects 0.000 claims description 4
• 208000026545 acidosis disease Diseases 0.000 claims description 4
• 208000018315 acute mountain sickness Diseases 0.000 claims description 4
• 125000002252 acyl group Chemical group 0.000 claims description 4
• 125000005354 acylalkyl group Chemical group 0.000 claims description 4
• 125000004423 acyloxy group Chemical group 0.000 claims description 4
• 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 4
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 4
• 125000003282 alkyl amino group Chemical group 0.000 claims description 4
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 4
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 4
• 125000005466 alkylenyl group Chemical group 0.000 claims description 4
• 125000000539 amino acid group Chemical group 0.000 claims description 4
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
• 125000003435 aroyl group Chemical group 0.000 claims description 4
• 125000005018 aryl alkenyl group Chemical group 0.000 claims description 4
• 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 4
• 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 4
• 125000001769 aryl amino group Chemical group 0.000 claims description 4
• 125000005141 aryl amino sulfonyl group Chemical group 0.000 claims description 4
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 4
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 4
• 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 4
• 125000005421 aryl sulfonamido group Chemical group 0.000 claims description 4
• 125000005110 aryl thio group Chemical group 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000001589 carboacyl group Chemical group 0.000 claims description 4
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
• 238000007675 cardiac surgery Methods 0.000 claims description 4
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
• 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 4
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
• 230000006378 damage Effects 0.000 claims description 4
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
• 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 4
• 208000022195 farmer lung disease Diseases 0.000 claims description 4
• 125000004967 formylalkyl group Chemical group 0.000 claims description 4
• 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 4
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 4
• 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 4
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 4
• 125000005241 heteroarylamino group Chemical group 0.000 claims description 4
• 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 4
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
• 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims description 4
• 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 4
• 125000005368 heteroarylthio group Chemical group 0.000 claims description 4
• 230000007954 hypoxia Effects 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 230000002401 inhibitory effect Effects 0.000 claims description 4
• 208000014674 injury Diseases 0.000 claims description 4
• 201000002652 newborn respiratory distress syndrome Diseases 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 230000009984 peri-natal effect Effects 0.000 claims description 4
• 208000004594 persistent fetal circulation syndrome Diseases 0.000 claims description 4
• 239000000651 prodrug Substances 0.000 claims description 4
• 229940002612 prodrug Drugs 0.000 claims description 4
• 229940048914 protamine Drugs 0.000 claims description 4
• 208000002815 pulmonary hypertension Diseases 0.000 claims description 4
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
• 239000011593 sulfur Substances 0.000 claims description 4
• 208000011580 syndromic disease Diseases 0.000 claims description 4
• 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 claims description 4
• KAXFOSOXUNYWRV-IYSWYEEDSA-N (2s)-2-amino-3-[(2r)-2-(1-aminoethylideneamino)propyl]sulfanylpropanoic acid Chemical compound CC(=N)N[C@H](C)CSC[C@@H](N)C(O)=O KAXFOSOXUNYWRV-IYSWYEEDSA-N 0.000 claims description 3
• KAXFOSOXUNYWRV-CAHLUQPWSA-N (2s)-2-amino-3-[(2s)-2-(1-aminoethylideneamino)propyl]sulfanylpropanoic acid Chemical compound CC(=N)N[C@@H](C)CSC[C@@H](N)C(O)=O KAXFOSOXUNYWRV-CAHLUQPWSA-N 0.000 claims description 3
• GPMLMWSFTHYNMU-VMKBVTSJSA-N (e,2r)-2-amino-7-(1-aminoethylideneamino)-6-fluoro-2-methylhept-5-enoic acid Chemical compound CC(=N)NC\C(F)=C/CC[C@@](C)(N)C(O)=O GPMLMWSFTHYNMU-VMKBVTSJSA-N 0.000 claims description 3
• GPMLMWSFTHYNMU-GOJXHPMJSA-N (e,2s)-2-amino-7-(1-aminoethylideneamino)-6-fluoro-2-methylhept-5-enoic acid Chemical compound CC(=N)NC\C(F)=C/CC[C@](C)(N)C(O)=O GPMLMWSFTHYNMU-GOJXHPMJSA-N 0.000 claims description 3
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 3
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 3
• 150000004683 dihydrates Chemical class 0.000 claims description 3
• ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 claims description 3
• 239000000236 nitric oxide synthase inhibitor Substances 0.000 claims description 3
• DHJNMQLRMOVIRR-VIFPVBQESA-N (2S)-2-[2-(1-aminoethylideneamino)ethylsulfanylmethoxy]-3-hydroxy-2-(methylamino)propanoic acid Chemical compound N=C(C)NCCSCO[C@@](NC)(CO)C(=O)O DHJNMQLRMOVIRR-VIFPVBQESA-N 0.000 claims description 2
• NWBJAUFHPXRBKI-QMMMGPOBSA-N (2r)-2-amino-3-[2-(1-aminoethylideneamino)ethylsulfanyl]-2-methylpropanoic acid Chemical compound CC(=N)NCCSC[C@](C)(N)C(O)=O NWBJAUFHPXRBKI-QMMMGPOBSA-N 0.000 claims description 2
• ZXQNVEYPDCBTLD-CYQMCQFNSA-N (2r)-2-amino-3-[2-(1-aminoethylideneamino)ethylsulfinyl]-2-methylpropanoic acid Chemical compound CC(=N)NCCS(=O)C[C@](C)(N)C(O)=O ZXQNVEYPDCBTLD-CYQMCQFNSA-N 0.000 claims description 2
• LOBRQMHOHPDZKT-JZGIKJSDSA-N (2r)-2-amino-3-[2-(1-aminoethylideneamino)ethylsulfonyl]-2-methylpropanoic acid;dihydrochloride Chemical compound Cl.Cl.CC(=N)NCCS(=O)(=O)C[C@](C)(N)C(O)=O LOBRQMHOHPDZKT-JZGIKJSDSA-N 0.000 claims description 2
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 2
• AWZAWNNQJYZQAS-CDAZIORVSA-N (e,2r)-2-amino-6-(1-aminoethylideneamino)-2-methylhex-4-enoic acid Chemical compound CC(=N)NC\C=C\C[C@@](C)(N)C(O)=O AWZAWNNQJYZQAS-CDAZIORVSA-N 0.000 claims description 2
• VQGCWTDMOOOHCH-HOOMWESVSA-N (e,2r)-2-amino-7-(1-aminoethylideneamino)-6-fluorohept-5-enoic acid Chemical compound CC(=N)NC\C(F)=C/CC[C@@H](N)C(O)=O VQGCWTDMOOOHCH-HOOMWESVSA-N 0.000 claims description 2
• GRHKBOWNVJMUAP-MRSNMJRISA-N (e,2s)-2-amino-6-[(2r)-7-amino-3,4,5,6-tetrahydro-2h-azepin-2-yl]hex-4-enoic acid Chemical compound OC(=O)[C@@H](N)C\C=C\C[C@H]1CCCCC(=N)N1 GRHKBOWNVJMUAP-MRSNMJRISA-N 0.000 claims description 2
• ZLBLGYXDADNGOG-DKCNVOGISA-N (e,2s)-2-amino-6-fluoro-7-[1-(hydroxyamino)ethylideneamino]hept-5-enoic acid Chemical compound ON=C(C)NC\C(F)=C/CC[C@H](N)C(O)=O ZLBLGYXDADNGOG-DKCNVOGISA-N 0.000 claims description 2
• GRHKBOWNVJMUAP-CVLTWBRKSA-N (z,2s)-2-amino-6-[(2r)-7-amino-3,4,5,6-tetrahydro-2h-azepin-2-yl]hex-4-enoic acid Chemical compound OC(=O)[C@@H](N)C\C=C/C[C@H]1CCCCC(=N)N1 GRHKBOWNVJMUAP-CVLTWBRKSA-N 0.000 claims description 2
• OSRZMBVYRBQGFG-UHFFFAOYSA-N 2-amino-6-(1-aminoethylideneamino)-2-methylhex-4-ynoic acid Chemical group CC(=N)NCC#CCC(C)(N)C(O)=O OSRZMBVYRBQGFG-UHFFFAOYSA-N 0.000 claims description 2
• RFEBDZANCVHDLP-UHFFFAOYSA-N 3-[(4-cyanophenyl)methylamino]-6-(trifluoromethyl)quinoxaline-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=C(C(F)(F)F)C=C2N=C1NCC1=CC=C(C#N)C=C1 RFEBDZANCVHDLP-UHFFFAOYSA-N 0.000 claims description 2
• NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 claims description 2
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• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
• 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 36
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
• 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
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• BGGZJBNSFJANAK-UHFFFAOYSA-N methyl 2-amino-2-methyl-7-(3-methyl-5-oxo-1,2,4-oxadiazol-4-yl)hept-5-enoate Chemical compound COC(=O)C(C)(N)CCC=CCN1C(C)=NOC1=O BGGZJBNSFJANAK-UHFFFAOYSA-N 0.000 description 1
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• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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• DBSKLZRMGLQODM-UHFFFAOYSA-M potassium 3-methyl-5-oxo-1,2,4-oxadiazole-2-carboxylate Chemical compound CC=1N(OC(N=1)=O)C(=O)[O-].[K+] DBSKLZRMGLQODM-UHFFFAOYSA-M 0.000 description 1
• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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• LJCNRYVRMXRIQR-UHFFFAOYSA-L potassium sodium tartrate Chemical compound [Na+].[K+].[O-]C(=O)C(O)C(O)C([O-])=O LJCNRYVRMXRIQR-UHFFFAOYSA-L 0.000 description 1
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• VFIZBHJTOHUOEK-UHFFFAOYSA-N s-ethylisothiourea Chemical compound CCSC(N)=N VFIZBHJTOHUOEK-UHFFFAOYSA-N 0.000 description 1
• 230000037390 scarring Effects 0.000 description 1
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• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
• WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
• QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
• HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
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• 229910001220 stainless steel Inorganic materials 0.000 description 1
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• TZRQZPMQUXEZMC-UHFFFAOYSA-N tert-butyl n-(2-bromoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCBr TZRQZPMQUXEZMC-UHFFFAOYSA-N 0.000 description 1
• FVQYBAASQSUZOP-UHFFFAOYSA-N tert-butyl n-(4-chlorobut-2-ynyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC#CCCl FVQYBAASQSUZOP-UHFFFAOYSA-N 0.000 description 1
• BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
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• GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
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• PIEPQKCYPFFYMG-UHFFFAOYSA-N tris acetate Chemical compound CC(O)=O.OCC(N)(CO)CO PIEPQKCYPFFYMG-UHFFFAOYSA-N 0.000 description 1
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