IL91063A

IL91063A - 5,6,7,8-טטרהידרו - h4-תיאזולו ]b-4 ,5[ אזפנים, הכנתם ותכשירים המכילים אותם לעיכוב ליפואוקסיגנאזה ויצירת ליפופראוקסיד

5,6,7,8-טטרהידרו - h4-תיאזולו ]b-4 ,5[ אזפנים, הכנתם ותכשירים המכילים אותם לעיכוב ליפואוקסיגנאזה ויצירת ליפופראוקסיד

Info

Publication number: IL91063A
Authority: IL; Israel
Prior art keywords: group; compound; substituted; amino; thiazolo
Prior art date: 1988-07-22

Application number

IL9106389A

Other languages

English (en)

Other versions

IL91063A0 (en

Original Assignee

Takeda Chemical Industries Ltd

Priority date

1988-07-22

Filing date

1989-07-21

Publication date

1994-12-29

1989-07-21 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1990-02-09 Publication of IL91063A0 publication Critical patent/IL91063A0/xx

1994-12-29 Publication of IL91063A publication Critical patent/IL91063A/he

Links

230000015572 biosynthetic process Effects 0.000 title claims abstract description 33
230000002401 inhibitory effect Effects 0.000 title claims abstract description 24
102000003820 Lipoxygenases Human genes 0.000 title claims description 8
108090000128 Lipoxygenases Proteins 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title claims description 5
239000000203 mixture Substances 0.000 title description 72
150000001538 azepines Chemical class 0.000 title description 2
125000003118 aryl group Chemical group 0.000 claims abstract description 32
125000001931 aliphatic group Chemical group 0.000 claims abstract description 29
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
125000001589 carboacyl group Chemical group 0.000 claims abstract description 15
125000002252 acyl group Chemical group 0.000 claims abstract description 9
150000001875 compounds Chemical class 0.000 claims description 270
238000000034 method Methods 0.000 claims description 145
-1 nitro, amino Chemical group 0.000 claims description 138
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 70
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 35
125000000217 alkyl group Chemical group 0.000 claims description 33
125000001424 substituent group Chemical group 0.000 claims description 28
238000006243 chemical reaction Methods 0.000 claims description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 18
229910052736 halogen Inorganic materials 0.000 claims description 15
150000002367 halogens Chemical class 0.000 claims description 15
239000003795 chemical substances by application Substances 0.000 claims description 14
125000003342 alkenyl group Chemical group 0.000 claims description 13
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
125000000304 alkynyl group Chemical group 0.000 claims description 10
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 9
229920006395 saturated elastomer Polymers 0.000 claims description 9
125000004414 alkyl thio group Chemical group 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
125000004122 cyclic group Chemical group 0.000 claims description 5
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
125000002837 carbocyclic group Chemical group 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 2
230000008569 process Effects 0.000 claims description 2
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 1
PFGSHLUUDKSOKG-UHFFFAOYSA-N 2-[2-(2,3-dimethoxyphenyl)ethenyl]-5,6,7,8-tetrahydro-4h-[1,3]thiazolo[5,4-b]azepine Chemical compound COC1=CC=CC(C=CC=2SC=3NCCCCC=3N=2)=C1OC PFGSHLUUDKSOKG-UHFFFAOYSA-N 0.000 claims 1
SGZFKGOOQPVXCY-UHFFFAOYSA-N 2-[2-(2-methoxy-3-methylphenyl)ethenyl]-5,6,7,8-tetrahydro-4h-[1,3]thiazolo[5,4-b]azepine Chemical compound COC1=C(C)C=CC=C1C=CC(S1)=NC2=C1NCCCC2 SGZFKGOOQPVXCY-UHFFFAOYSA-N 0.000 claims 1
QDYZNDCOSOHBIK-UHFFFAOYSA-N 2-[2-(3,4,5-trimethoxyphenyl)ethenyl]-5,6,7,8-tetrahydro-4h-[1,3]thiazolo[5,4-b]azepine Chemical compound COC1=C(OC)C(OC)=CC(C=CC=2SC=3NCCCCC=3N=2)=C1 QDYZNDCOSOHBIK-UHFFFAOYSA-N 0.000 claims 1
ZEHJQOQWEYEYKN-UHFFFAOYSA-N 2-[2-(4-methoxy-3-methylphenyl)ethenyl]-5,6,7,8-tetrahydro-4h-[1,3]thiazolo[5,4-b]azepine Chemical compound C1=C(C)C(OC)=CC=C1C=CC(S1)=NC2=C1NCCCC2 ZEHJQOQWEYEYKN-UHFFFAOYSA-N 0.000 claims 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
WRDQLFOQEXCULO-UHFFFAOYSA-N 2h-[1,3]thiazolo[5,4-b]azepine Chemical class C1=CC=CC2=NCSC2=N1 WRDQLFOQEXCULO-UHFFFAOYSA-N 0.000 abstract description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 159
238000000921 elemental analysis Methods 0.000 description 134
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 103
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 95
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 93
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 93
101150041968 CDC13 gene Proteins 0.000 description 91
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 49
229910000041 hydrogen chloride Inorganic materials 0.000 description 49
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 41
230000003472 neutralizing effect Effects 0.000 description 40
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
239000000243 solution Substances 0.000 description 32
238000005755 formation reaction Methods 0.000 description 30
230000002829 reductive effect Effects 0.000 description 29
239000002904 solvent Substances 0.000 description 29
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 19
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 19
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
239000000741 silica gel Substances 0.000 description 16
229910002027 silica gel Inorganic materials 0.000 description 16
238000001816 cooling Methods 0.000 description 15
238000012360 testing method Methods 0.000 description 15
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
PJHKXESPJOFGOA-UHFFFAOYSA-N 1h-azepine;dihydrochloride Chemical compound Cl.Cl.N1C=CC=CC=C1 PJHKXESPJOFGOA-UHFFFAOYSA-N 0.000 description 11
230000005764 inhibitory process Effects 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
229940086542 triethylamine Drugs 0.000 description 11
239000002253 acid Substances 0.000 description 10
KUKJHGXXZWHSBG-GMPNNLDHSA-N 12-HHTrE Chemical compound CCCCCC(O)\C=C\C=C\C\C=C\CCCC(O)=O KUKJHGXXZWHSBG-GMPNNLDHSA-N 0.000 description 9
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
230000010410 reperfusion Effects 0.000 description 8
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
201000010099 disease Diseases 0.000 description 7
239000003814 drug Substances 0.000 description 7
229940073584 methylene chloride Drugs 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
AJUMGSLQADLWKL-UHFFFAOYSA-N 1h-azepine;hydrochloride Chemical compound Cl.N1C=CC=CC=C1 AJUMGSLQADLWKL-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
230000009471 action Effects 0.000 description 6
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 6
235000006408 oxalic acid Nutrition 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
BOWUOGIPSRVRSJ-UHFFFAOYSA-N 2-aminohexano-6-lactam Chemical compound NC1CCCCNC1=O BOWUOGIPSRVRSJ-UHFFFAOYSA-N 0.000 description 5
KGIJOOYOSFUGPC-CABOLEKPSA-N 5-HETE Natural products CCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](O)CCCC(O)=O KGIJOOYOSFUGPC-CABOLEKPSA-N 0.000 description 5
230000010933 acylation Effects 0.000 description 5
238000005917 acylation reaction Methods 0.000 description 5
125000003282 alkyl amino group Chemical group 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
230000002490 cerebral effect Effects 0.000 description 5
239000013078 crystal Substances 0.000 description 5
238000004821 distillation Methods 0.000 description 5
229940079593 drug Drugs 0.000 description 5
239000003112 inhibitor Substances 0.000 description 5
210000004623 platelet-rich plasma Anatomy 0.000 description 5
239000000843 powder Substances 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
MHJQKVZUHVVCRV-UHFFFAOYSA-N 2-phenyl-5,6,7,8-tetrahydro-4h-[1,3]thiazolo[5,4-b]azepine Chemical compound S1C=2NCCCCC=2N=C1C1=CC=CC=C1 MHJQKVZUHVVCRV-UHFFFAOYSA-N 0.000 description 4
VTQGYRVGBASLDF-UHFFFAOYSA-N 4-aminoazepan-2-one Chemical compound NC1CCCNC(=O)C1 VTQGYRVGBASLDF-UHFFFAOYSA-N 0.000 description 4
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
KGIJOOYOSFUGPC-MSFIICATSA-N 5-Hydroxyeicosatetraenoic acid Chemical compound CCCCCC=CCC=CCC=C\C=C\[C@@H](O)CCCC(O)=O KGIJOOYOSFUGPC-MSFIICATSA-N 0.000 description 4
206010008190 Cerebrovascular accident Diseases 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 4
108090000790 Enzymes Proteins 0.000 description 4
206010061218 Inflammation Diseases 0.000 description 4
241000699666 Mus <mouse, genus> Species 0.000 description 4
208000006011 Stroke Diseases 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
230000006399 behavior Effects 0.000 description 4
210000004369 blood Anatomy 0.000 description 4
239000008280 blood Substances 0.000 description 4
210000004556 brain Anatomy 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
206010008118 cerebral infarction Diseases 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
125000004093 cyano group Chemical group *C#N 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
229960002089 ferrous chloride Drugs 0.000 description 4
238000001914 filtration Methods 0.000 description 4
125000000623 heterocyclic group Chemical group 0.000 description 4
230000004054 inflammatory process Effects 0.000 description 4
NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 4
TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
125000004076 pyridyl group Chemical group 0.000 description 4
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 3
INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
229940100198 alkylating agent Drugs 0.000 description 3
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
230000008485 antagonism Effects 0.000 description 3
230000003078 antioxidant effect Effects 0.000 description 3
229940114079 arachidonic acid Drugs 0.000 description 3
235000021342 arachidonic acid Nutrition 0.000 description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
208000026106 cerebrovascular disease Diseases 0.000 description 3
230000008859 change Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
239000001530 fumaric acid Substances 0.000 description 3
210000002216 heart Anatomy 0.000 description 3
208000006454 hepatitis Diseases 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
150000002617 leukotrienes Chemical class 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
201000008383 nephritis Diseases 0.000 description 3
125000004043 oxo group Chemical group O=* 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
229910052698 phosphorus Inorganic materials 0.000 description 3
239000011574 phosphorus Substances 0.000 description 3
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
HJVAVGOPTDJYOJ-UHFFFAOYSA-N 2-amino-4,5-dimethoxybenzoic acid Chemical compound COC1=CC(N)=C(C(O)=O)C=C1OC HJVAVGOPTDJYOJ-UHFFFAOYSA-N 0.000 description 2
AXEVMSJERWWREB-UHFFFAOYSA-N 2-methyl-5-(5,6,7,8-tetrahydro-4h-[1,3]thiazolo[5,4-b]azepin-2-yl)benzonitrile Chemical compound C1=C(C#N)C(C)=CC=C1C(S1)=NC2=C1NCCCC2 AXEVMSJERWWREB-UHFFFAOYSA-N 0.000 description 2
QURCVMIEKCOAJU-UHFFFAOYSA-N 3-Hydroxy 4-Methoxy Cinnamic acid Chemical compound COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 2
XKFIFYROMAAUDL-UHFFFAOYSA-N 3-amino-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1N XKFIFYROMAAUDL-UHFFFAOYSA-N 0.000 description 2
NMJXONBGHJOWPZ-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydro-4h-[1,3]thiazolo[5,4-b]azepin-2-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C(S1)=NC2=C1NCCCC2 NMJXONBGHJOWPZ-UHFFFAOYSA-N 0.000 description 2
RDEYORKJEDLLDB-DQVHGTJVSA-N 5-Hydroperoxyeicosatetraenoic acid Chemical compound CCCCCCCCCCC\C=C\C=C\C(\OO)=C\C=C\C(O)=O RDEYORKJEDLLDB-DQVHGTJVSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 description 2
108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 2
206010003210 Arteriosclerosis Diseases 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
201000006474 Brain Ischemia Diseases 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
RAGYQTGMAGPCHM-UHFFFAOYSA-N CC(C)C1=CC=C(C=C1)C=CC(=O)C2CCCNC(=O)C2N Chemical compound CC(C)C1=CC=C(C=C1)C=CC(=O)C2CCCNC(=O)C2N RAGYQTGMAGPCHM-UHFFFAOYSA-N 0.000 description 2
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