TW201035102A - Sulfonylated tetrahydroazolopyrazines and their use as medicinal products - Google Patents

Info

Publication number

TW201035102A

TW201035102A TW099105566A TW99105566A TW201035102A TW 201035102 A TW201035102 A TW 201035102A TW 099105566 A TW099105566 A TW 099105566A TW 99105566 A TW99105566 A TW 99105566A TW 201035102 A TW201035102 A TW 201035102A

Authority

TW

Taiwan

Prior art keywords

group

carbon atoms

methyl

tetrahydro

phenyl

Prior art date

2009-03-04

Links

• Espacenet
• Global Dossier
• Discuss

• WEXJJSPMIBHSKF-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-pyrrolo[2,3-b]pyrazine Chemical class N1CCNC2=C1C=CN2 WEXJJSPMIBHSKF-UHFFFAOYSA-N 0.000 title abstract description 11
• 229940126601 medicinal product Drugs 0.000 title abstract 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 102
• 238000002360 preparation method Methods 0.000 claims abstract description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 596
• -1 oxythio group Chemical group 0.000 claims description 374
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 267
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 197
• 125000000217 alkyl group Chemical group 0.000 claims description 186
• 125000003118 aryl group Chemical group 0.000 claims description 174
• 125000001424 substituent group Chemical group 0.000 claims description 164
• 125000001072 heteroaryl group Chemical group 0.000 claims description 155
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 147
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 144
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 130
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 116
• 125000002947 alkylene group Chemical group 0.000 claims description 113
• 239000000203 mixture Substances 0.000 claims description 110
• 239000002585 base Substances 0.000 claims description 108
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 102
• FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 73
• 125000004429 atom Chemical group 0.000 claims description 66
• 125000003277 amino group Chemical group 0.000 claims description 63
• 229910052731 fluorine Inorganic materials 0.000 claims description 61
• 229910052757 nitrogen Inorganic materials 0.000 claims description 61
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 58
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 58
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 56
• 125000004076 pyridyl group Chemical group 0.000 claims description 55
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 49
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 48
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 44
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 42
• 239000011737 fluorine Substances 0.000 claims description 42
• 125000003545 alkoxy group Chemical group 0.000 claims description 41
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 41
• 229910052799 carbon Inorganic materials 0.000 claims description 39
• OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 37
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 37
• 229910052801 chlorine Inorganic materials 0.000 claims description 36
• 229910052739 hydrogen Inorganic materials 0.000 claims description 36
• 239000001257 hydrogen Substances 0.000 claims description 36
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 34
• 239000000460 chlorine Substances 0.000 claims description 33
• 125000001544 thienyl group Chemical group 0.000 claims description 33
• 150000001721 carbon Chemical group 0.000 claims description 32
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 32
• 125000001425 triazolyl group Chemical group 0.000 claims description 32
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 31
• 125000002883 imidazolyl group Chemical group 0.000 claims description 31
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 31
• 125000000623 heterocyclic group Chemical group 0.000 claims description 30
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 29
• 239000007789 gas Substances 0.000 claims description 28
• 125000000335 thiazolyl group Chemical group 0.000 claims description 26
• 208000002193 Pain Diseases 0.000 claims description 23
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
• 125000000524 functional group Chemical group 0.000 claims description 22
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 21
• 125000002393 azetidinyl group Chemical group 0.000 claims description 21
• 125000001153 fluoro group Chemical group F* 0.000 claims description 21
• 125000003386 piperidinyl group Chemical group 0.000 claims description 21
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 21
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 20
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 20
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 20
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 19
• 125000004043 oxo group Chemical group O=* 0.000 claims description 19
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
• 229910052794 bromium Inorganic materials 0.000 claims description 18
• 125000001624 naphthyl group Chemical group 0.000 claims description 18
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• GXWNSJYVSIJRLS-UHFFFAOYSA-N 6-bromo-8-methylimidazo[1,2-a]pyrazine Chemical compound CC1=NC(Br)=CN2C=CN=C12 GXWNSJYVSIJRLS-UHFFFAOYSA-N 0.000 claims description 15
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 230000036407 pain Effects 0.000 claims description 15
• 125000004419 alkynylene group Chemical group 0.000 claims description 13
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
• 238000011282 treatment Methods 0.000 claims description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
• 125000004122 cyclic group Chemical group 0.000 claims description 12
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 12
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
• 239000000126 substance Substances 0.000 claims description 12
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 12
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 11
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 10
• 238000006467 substitution reaction Methods 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 9
• 201000010099 disease Diseases 0.000 claims description 9
• 125000002541 furyl group Chemical group 0.000 claims description 9
• 150000003839 salts Chemical class 0.000 claims description 9
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 9
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
• 125000004450 alkenylene group Chemical group 0.000 claims description 8
• 125000005529 alkyleneoxy group Chemical group 0.000 claims description 8
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
• 125000004891 1-methylpropylamino group Chemical group CC(CC)N* 0.000 claims description 7
• 150000001412 amines Chemical class 0.000 claims description 7
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 7
• 229910052740 iodine Inorganic materials 0.000 claims description 7
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 7
• 150000002576 ketones Chemical class 0.000 claims description 7
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 7
• 230000007823 neuropathy Effects 0.000 claims description 7
• 201000001119 neuropathy Diseases 0.000 claims description 7
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 7
• 208000033808 peripheral neuropathy Diseases 0.000 claims description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
• AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 6
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000000094 2-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 6
• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 6
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 6
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• 150000001923 cyclic compounds Chemical class 0.000 claims description 6
• 125000005842 heteroatom Chemical group 0.000 claims description 6
• 125000001041 indolyl group Chemical group 0.000 claims description 6
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 6
• 125000004434 sulfur atom Chemical group 0.000 claims description 6
• 125000003944 tolyl group Chemical group 0.000 claims description 6
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 5
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 5
• RSJKGSCJYJTIGS-UHFFFAOYSA-N N-undecane Natural products CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 5
• 208000008589 Obesity Diseases 0.000 claims description 5
• 206010040070 Septic Shock Diseases 0.000 claims description 5
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 5
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
• AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 5
• 239000011630 iodine Substances 0.000 claims description 5
• 235000020824 obesity Nutrition 0.000 claims description 5
• 150000002923 oximes Chemical group 0.000 claims description 5
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 230000036303 septic shock Effects 0.000 claims description 5
• IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 5
• 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 4
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
• 208000000094 Chronic Pain Diseases 0.000 claims description 4
• 201000004624 Dermatitis Diseases 0.000 claims description 4
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
• 208000005298 acute pain Diseases 0.000 claims description 4
• 125000005605 benzo group Chemical group 0.000 claims description 4
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 150000001924 cycloalkanes Chemical class 0.000 claims description 4
• 206010012601 diabetes mellitus Diseases 0.000 claims description 4
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
• 229940127557 pharmaceutical product Drugs 0.000 claims description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 230000010410 reperfusion Effects 0.000 claims description 4
• 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 claims description 4
• IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 claims description 4
• LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims description 3
• JCHJBEZBHANKGA-UHFFFAOYSA-N 1-methoxy-3,5-dimethylbenzene Chemical compound COC1=CC(C)=CC(C)=C1 JCHJBEZBHANKGA-UHFFFAOYSA-N 0.000 claims description 3
• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 3
• LUZDYPLAQQGJEA-UHFFFAOYSA-N 2-Methoxynaphthalene Chemical compound C1=CC=CC2=CC(OC)=CC=C21 LUZDYPLAQQGJEA-UHFFFAOYSA-N 0.000 claims description 3
• NEURYOYRKPFLKH-UHFFFAOYSA-N 2-chloro-1-isocyanato-4-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC=C(N=C=O)C(Cl)=C1 NEURYOYRKPFLKH-UHFFFAOYSA-N 0.000 claims description 3
• 239000005711 Benzoic acid Substances 0.000 claims description 3
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• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
• 208000019695 Migraine disease Diseases 0.000 claims description 3
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
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• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 3
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
• RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 3
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• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
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• KIPSRYDSZQRPEA-UHFFFAOYSA-N 2,2,2-trifluoroethanamine Chemical compound NCC(F)(F)F KIPSRYDSZQRPEA-UHFFFAOYSA-N 0.000 claims description 2
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• 150000001408 amides Chemical class 0.000 claims description 2
• 125000005427 anthranyl group Chemical group 0.000 claims description 2
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• 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 2
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
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• 229910052707 ruthenium Inorganic materials 0.000 claims description 2
• 238000003860 storage Methods 0.000 claims description 2
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
• 238000012546 transfer Methods 0.000 claims description 2
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• MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims 3
• OQJVXNHMUWQQEW-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrazine Chemical compound C1CNC=CN1 OQJVXNHMUWQQEW-UHFFFAOYSA-N 0.000 claims 2
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