TW201704206A - 環狀化合物 - Google Patents

Info

Publication number

TW201704206A

TW201704206A TW105114092A TW105114092A TW201704206A TW 201704206 A TW201704206 A TW 201704206A TW 105114092 A TW105114092 A TW 105114092A TW 105114092 A TW105114092 A TW 105114092A TW 201704206 A TW201704206 A TW 201704206A

Authority

TW

Taiwan

Prior art keywords

group

compound

mixture

acid

ethyl

Prior art date

2015-05-08

Links

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• 150000001923 cyclic compounds Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 188
• 150000003839 salts Chemical class 0.000 claims abstract description 57
• 206010063837 Reperfusion injury Diseases 0.000 claims abstract description 27
• 208000012947 ischemia reperfusion injury Diseases 0.000 claims abstract description 26
• 238000002512 chemotherapy Methods 0.000 claims abstract description 24
• 208000004296 neuralgia Diseases 0.000 claims abstract description 15
• 208000021722 neuropathic pain Diseases 0.000 claims abstract description 14
• 206010067125 Liver injury Diseases 0.000 claims abstract description 13
• 208000033808 peripheral neuropathy Diseases 0.000 claims abstract description 12
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 10
• 231100000753 hepatic injury Toxicity 0.000 claims abstract description 9
• 125000001424 substituent group Chemical group 0.000 claims description 90
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 65
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
• 239000003795 chemical substances by application Substances 0.000 claims description 33
• 238000002360 preparation method Methods 0.000 claims description 27
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 25
• LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 24
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
• HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 20
• 125000005843 halogen group Chemical group 0.000 claims description 19
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 15
• RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 14
• 208000023275 Autoimmune disease Diseases 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 11
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• 230000011664 signaling Effects 0.000 abstract description 13
• 230000002401 inhibitory effect Effects 0.000 abstract description 6
• 208000015114 central nervous system disease Diseases 0.000 abstract description 5
• 229940126585 therapeutic drug Drugs 0.000 abstract description 2
• 102000008233 Toll-Like Receptor 4 Human genes 0.000 abstract 2
• 108010060804 Toll-Like Receptor 4 Proteins 0.000 abstract 2
• 230000003449 preventive effect Effects 0.000 abstract 1
• -1 cyclohexane Alkene Chemical class 0.000 description 334
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 315
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 166
• 239000000203 mixture Substances 0.000 description 137
• 235000019439 ethyl acetate Nutrition 0.000 description 120
• 235000002639 sodium chloride Nutrition 0.000 description 109
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 105
• 238000000034 method Methods 0.000 description 92
• 239000003814 drug Substances 0.000 description 91
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 88
• 229940079593 drug Drugs 0.000 description 83
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 76
• 229920006395 saturated elastomer Polymers 0.000 description 70
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 66
• 239000011541 reaction mixture Substances 0.000 description 60
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 58
• 239000007788 liquid Substances 0.000 description 58
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
• 239000007864 aqueous solution Substances 0.000 description 53
• 239000000284 extract Substances 0.000 description 53
• 239000011780 sodium chloride Substances 0.000 description 52
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
• 238000005481 NMR spectroscopy Methods 0.000 description 44
• 238000001816 cooling Methods 0.000 description 43
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 41
• 125000003118 aryl group Chemical group 0.000 description 40
• 239000002904 solvent Substances 0.000 description 39
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 38
• 235000019341 magnesium sulphate Nutrition 0.000 description 38
• 239000007787 solid Substances 0.000 description 38
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 37
• 239000002585 base Substances 0.000 description 37
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
• 238000011282 treatment Methods 0.000 description 33
• 239000003153 chemical reaction reagent Substances 0.000 description 32
• 230000002829 reductive effect Effects 0.000 description 32
• 239000000243 solution Substances 0.000 description 32
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
• 239000003112 inhibitor Substances 0.000 description 29
• 238000006243 chemical reaction Methods 0.000 description 28
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 27
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 26
• 201000010099 disease Diseases 0.000 description 24
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 22
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 22
• 125000000623 heterocyclic group Chemical group 0.000 description 22
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
• 238000010898 silica gel chromatography Methods 0.000 description 21
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
• 239000002253 acid Substances 0.000 description 20
• 150000001412 amines Chemical class 0.000 description 20
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
• 125000000217 alkyl group Chemical group 0.000 description 18
• 125000002950 monocyclic group Chemical group 0.000 description 18
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 16
• 208000002193 Pain Diseases 0.000 description 16
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
• 238000002425 crystallisation Methods 0.000 description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
• 230000003287 optical effect Effects 0.000 description 16
• 229910052938 sodium sulfate Inorganic materials 0.000 description 16
• 235000011152 sodium sulphate Nutrition 0.000 description 16
• 206010057190 Respiratory tract infections Diseases 0.000 description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• 125000003396 thiol group Chemical group [H]S* 0.000 description 15
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 14
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 14
• 230000036407 pain Effects 0.000 description 14
• 239000000126 substance Substances 0.000 description 14
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 12
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
• 125000003277 amino group Chemical group 0.000 description 12
• 125000003710 aryl alkyl group Chemical group 0.000 description 12
• 229910052799 carbon Inorganic materials 0.000 description 12
• 230000008025 crystallization Effects 0.000 description 12
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 12
• 239000012071 phase Substances 0.000 description 12
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 11
• 230000037396 body weight Effects 0.000 description 11
• 238000004440 column chromatography Methods 0.000 description 11
• 239000000825 pharmaceutical preparation Substances 0.000 description 11
• 235000017557 sodium bicarbonate Nutrition 0.000 description 11
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
• 239000005557 antagonist Substances 0.000 description 10
• 229910052801 chlorine Inorganic materials 0.000 description 10
• 150000001925 cycloalkenes Chemical class 0.000 description 10
• 238000001914 filtration Methods 0.000 description 10
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
• 238000000926 separation method Methods 0.000 description 10
• 125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 description 9
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 9
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 9
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 9
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
• 229960005286 carbaryl Drugs 0.000 description 9
• CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 9
• 239000002934 diuretic Substances 0.000 description 9
• 238000004128 high performance liquid chromatography Methods 0.000 description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
• 229910000027 potassium carbonate Inorganic materials 0.000 description 9
• 230000002265 prevention Effects 0.000 description 9
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 8
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 8
• 230000001154 acute effect Effects 0.000 description 8
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
• 150000002148 esters Chemical class 0.000 description 8
• 150000002430 hydrocarbons Chemical group 0.000 description 8
• 229910052757 nitrogen Inorganic materials 0.000 description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 description 8
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
• 125000006413 ring segment Chemical group 0.000 description 8
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 7
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 7
• 125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 7
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 7
• 229910052751 metal Inorganic materials 0.000 description 7
• 239000002184 metal Substances 0.000 description 7
• 150000007524 organic acids Chemical class 0.000 description 7
• 102000005962 receptors Human genes 0.000 description 7
• 108020003175 receptors Proteins 0.000 description 7
• 239000011734 sodium Substances 0.000 description 7
• 229910052708 sodium Inorganic materials 0.000 description 7
• 229940083542 sodium Drugs 0.000 description 7
• 239000010902 straw Substances 0.000 description 7
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 6
• OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
• FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 6
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• 241000124008 Mammalia Species 0.000 description 6
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
• PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 6
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 6
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 150000001335 aliphatic alkanes Chemical class 0.000 description 6
• 150000001350 alkyl halides Chemical class 0.000 description 6
• 239000003242 anti bacterial agent Substances 0.000 description 6
• 239000002246 antineoplastic agent Substances 0.000 description 6
• 150000001721 carbon Chemical group 0.000 description 6
• 125000001309 chloro group Chemical group Cl* 0.000 description 6
• 229940030606 diuretics Drugs 0.000 description 6
• 230000005496 eutectics Effects 0.000 description 6
• 229910052731 fluorine Inorganic materials 0.000 description 6
• 125000005842 heteroatom Chemical group 0.000 description 6
• 238000006460 hydrolysis reaction Methods 0.000 description 6
• 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 description 6
• 150000007530 organic bases Chemical class 0.000 description 6
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 6
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
• 239000000047 product Substances 0.000 description 6
• ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
• 239000012279 sodium borohydride Substances 0.000 description 6
• 229910000033 sodium borohydride Inorganic materials 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• 229910052717 sulfur Inorganic materials 0.000 description 6
• 238000003786 synthesis reaction Methods 0.000 description 6
• ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 6
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
• 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 6
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 5
• VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical group NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 5
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
• 239000002841 Lewis acid Substances 0.000 description 5
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 5
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
• 206010040047 Sepsis Diseases 0.000 description 5
• 206010040070 Septic Shock Diseases 0.000 description 5
• 229940041181 antineoplastic drug Drugs 0.000 description 5
• 150000004945 aromatic hydrocarbons Chemical group 0.000 description 5
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 5
• 125000004744 butyloxycarbonyl group Chemical group 0.000 description 5
• 239000013078 crystal Substances 0.000 description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
• 125000004185 ester group Chemical group 0.000 description 5
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
• LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 5
• 125000001153 fluoro group Chemical group F* 0.000 description 5
• 235000019253 formic acid Nutrition 0.000 description 5
• 150000007517 lewis acids Chemical class 0.000 description 5
• 238000004519 manufacturing process Methods 0.000 description 5
• 239000000463 material Substances 0.000 description 5
• 150000007522 mineralic acids Chemical class 0.000 description 5
• 210000000056 organ Anatomy 0.000 description 5
• 229910052760 oxygen Inorganic materials 0.000 description 5
• 125000004430 oxygen atom Chemical group O* 0.000 description 5
• WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 5
• 150000004032 porphyrins Chemical class 0.000 description 5
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
• 125000004434 sulfur atom Chemical group 0.000 description 5
• 208000011580 syndromic disease Diseases 0.000 description 5
• 229930192474 thiophene Natural products 0.000 description 5
• 150000003722 vitamin derivatives Chemical class 0.000 description 5
• 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 description 4
• DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 4
• HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical class NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
• 239000005541 ACE inhibitor Substances 0.000 description 4
• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
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