TW201119651A - Pharmaceutical composition comprising indole compound - Google Patents
Pharmaceutical composition comprising indole compound Download PDFInfo
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- TW201119651A TW201119651A TW099136045A TW99136045A TW201119651A TW 201119651 A TW201119651 A TW 201119651A TW 099136045 A TW099136045 A TW 099136045A TW 99136045 A TW99136045 A TW 99136045A TW 201119651 A TW201119651 A TW 201119651A
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- alkyl
- alkoxy
- aryl
- hydrogen
- Prior art date
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- -1 indole compound Chemical class 0.000 title claims abstract description 44
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 35
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title abstract 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title abstract 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 127
- 201000010099 disease Diseases 0.000 claims abstract description 42
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 42
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 31
- 206010063837 Reperfusion injury Diseases 0.000 claims abstract description 25
- 230000017074 necrotic cell death Effects 0.000 claims abstract description 24
- 230000006378 damage Effects 0.000 claims abstract description 20
- 230000002265 prevention Effects 0.000 claims abstract description 18
- 230000036542 oxidative stress Effects 0.000 claims abstract description 15
- 208000027418 Wounds and injury Diseases 0.000 claims abstract description 14
- 208000014674 injury Diseases 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 206010021143 Hypoxia Diseases 0.000 claims abstract description 9
- 230000001146 hypoxic effect Effects 0.000 claims abstract description 8
- 239000002537 cosmetic Substances 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 76
- 229910052739 hydrogen Inorganic materials 0.000 claims description 65
- 239000001257 hydrogen Substances 0.000 claims description 64
- 150000002431 hydrogen Chemical group 0.000 claims description 54
- 125000000623 heterocyclic group Chemical group 0.000 claims description 51
- 125000003545 alkoxy group Chemical group 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical group 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 210000004185 liver Anatomy 0.000 claims description 21
- 150000002825 nitriles Chemical group 0.000 claims description 21
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 21
- 239000003642 reactive oxygen metabolite Substances 0.000 claims description 19
- 206010028851 Necrosis Diseases 0.000 claims description 17
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 16
- 101100339431 Arabidopsis thaliana HMGB2 gene Proteins 0.000 claims description 15
- 108700010013 HMGB1 Proteins 0.000 claims description 15
- 101150021904 HMGB1 gene Proteins 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000003282 alkyl amino group Chemical group 0.000 claims description 13
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
- 208000006011 Stroke Diseases 0.000 claims description 7
- 241000700605 Viruses Species 0.000 claims description 7
- 239000000872 buffer Substances 0.000 claims description 7
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 7
- 230000004065 mitochondrial dysfunction Effects 0.000 claims description 7
- 208000010125 myocardial infarction Diseases 0.000 claims description 7
- 239000007845 reactive nitrogen species Substances 0.000 claims description 7
- 230000010410 reperfusion Effects 0.000 claims description 7
- 206010036790 Productive cough Diseases 0.000 claims description 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 230000000747 cardiac effect Effects 0.000 claims description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 210000003802 sputum Anatomy 0.000 claims description 6
- 208000024794 sputum Diseases 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 230000001476 alcoholic effect Effects 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 230000006793 arrhythmia Effects 0.000 claims description 5
- 206010003119 arrhythmia Diseases 0.000 claims description 5
- 230000001404 mediated effect Effects 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 238000002271 resection Methods 0.000 claims description 5
- 238000002054 transplantation Methods 0.000 claims description 5
- 208000035143 Bacterial infection Diseases 0.000 claims description 4
- 206010061218 Inflammation Diseases 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 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 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 208000019622 heart disease Diseases 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- 208000019423 liver disease Diseases 0.000 claims description 4
- 230000001338 necrotic effect Effects 0.000 claims description 4
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 4
- 239000002689 soil Substances 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 3
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 3
- 208000007082 Alcoholic Fatty Liver Diseases 0.000 claims description 3
- 208000014644 Brain disease Diseases 0.000 claims description 3
- 208000005189 Embolism Diseases 0.000 claims description 3
- 206010016262 Fatty liver alcoholic Diseases 0.000 claims description 3
- 206010033799 Paralysis Diseases 0.000 claims description 3
- 208000026594 alcoholic fatty liver disease Diseases 0.000 claims description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
- 230000003412 degenerative effect Effects 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 208000010706 fatty liver disease Diseases 0.000 claims description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 208000006454 hepatitis Diseases 0.000 claims description 3
- 231100000283 hepatitis Toxicity 0.000 claims description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 2
- 241000894006 Bacteria Species 0.000 claims description 2
- 206010051290 Central nervous system lesion Diseases 0.000 claims description 2
- 208000035473 Communicable disease Diseases 0.000 claims description 2
- 206010010904 Convulsion Diseases 0.000 claims description 2
- 208000023105 Huntington disease Diseases 0.000 claims description 2
- 201000009035 MERRF syndrome Diseases 0.000 claims description 2
- 201000002169 Mitochondrial myopathy Diseases 0.000 claims description 2
- 206010069825 Myoclonic epilepsy and ragged-red fibres Diseases 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 206010040047 Sepsis Diseases 0.000 claims description 2
- 208000036142 Viral infection Diseases 0.000 claims description 2
- 230000001154 acute effect Effects 0.000 claims description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 2
- 125000005264 aryl amine group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 210000004204 blood vessel Anatomy 0.000 claims description 2
- 238000001354 calcination Methods 0.000 claims description 2
- 208000031169 hemorrhagic disease Diseases 0.000 claims description 2
- 208000023692 inborn mitochondrial myopathy Diseases 0.000 claims description 2
- 208000006443 lactic acidosis Diseases 0.000 claims description 2
- 201000008482 osteoarthritis Diseases 0.000 claims description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 230000001629 suppression Effects 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 125000004149 thio group Chemical group *S* 0.000 claims description 2
- 241000712461 unidentified influenza virus Species 0.000 claims description 2
- 208000019553 vascular disease Diseases 0.000 claims description 2
- 230000003612 virological effect Effects 0.000 claims description 2
- 230000000007 visual effect Effects 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 4
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims 3
- 102000055207 HMGB1 Human genes 0.000 claims 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 3
- 125000005336 allyloxy group Chemical group 0.000 claims 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 3
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical group CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims 2
- 150000004982 aromatic amines Chemical group 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- WFYHAKOLBICHEZ-UHFFFAOYSA-N 3-[2-(1,3-benzodioxol-5-yl)-2-oxoethyl]-5-bromo-3-hydroxy-1h-indol-2-one Chemical compound O=C1NC2=CC=C(Br)C=C2C1(O)CC(=O)C1=CC=C(OCO2)C2=C1 WFYHAKOLBICHEZ-UHFFFAOYSA-N 0.000 claims 1
- 208000008964 Chemical and Drug Induced Liver Injury Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 206010072268 Drug-induced liver injury Diseases 0.000 claims 1
- 239000005792 Geraniol Chemical group 0.000 claims 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Chemical group CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims 1
- 208000031886 HIV Infections Diseases 0.000 claims 1
- 208000037357 HIV infectious disease Diseases 0.000 claims 1
- 101100491995 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) aro-1 gene Proteins 0.000 claims 1
- 208000003251 Pruritus Diseases 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 150000008052 alkyl sulfonates Chemical class 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 150000001356 alkyl thiols Chemical class 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 230000030833 cell death Effects 0.000 claims 1
- 238000002512 chemotherapy Methods 0.000 claims 1
- 125000006612 decyloxy group Chemical group 0.000 claims 1
- 201000008865 drug-induced hepatitis Diseases 0.000 claims 1
- 230000007613 environmental effect Effects 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- 229940113087 geraniol Drugs 0.000 claims 1
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000007803 itching Effects 0.000 claims 1
- 229920005610 lignin Polymers 0.000 claims 1
- 125000002560 nitrile group Chemical group 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- JSGHQDAEHDRLOI-UHFFFAOYSA-N oxomalononitrile Chemical group N#CC(=O)C#N JSGHQDAEHDRLOI-UHFFFAOYSA-N 0.000 claims 1
- 125000004354 sulfur functional group Chemical group 0.000 claims 1
- 210000003470 mitochondria Anatomy 0.000 abstract description 5
- 230000004064 dysfunction Effects 0.000 abstract description 2
- 230000000302 ischemic effect Effects 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 87
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 45
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- 238000006243 chemical reaction Methods 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
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- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
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- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 7
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- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 6
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
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| KR101304772B1 (ko) * | 2011-04-11 | 2013-09-05 | 인제대학교 산학협력단 | ＮｅｃｒｏＸ―５를 유효성분으로 포함하는 미토콘드리아 기능 조절용 조성물 |
| WO2013115457A1 (ko) * | 2012-01-31 | 2013-08-08 | 인제대학교 산학협력단 | ＮｅｃｒｏＸ를 함유하는 암 전이 억제용 조성물 |
| KR101400346B1 (ko) * | 2012-01-31 | 2014-05-30 | 인제대학교 산학협력단 | ＮｅｃｒｏＸ를 함유하는 암 전이 억제용 조성물 |
| CN113967215A (zh) * | 2014-04-18 | 2022-01-25 | Lg 化学株式会社 | 用于预防或治疗脂肪肝疾病的组合物 |
| CA2953387C (en) * | 2014-06-30 | 2023-11-28 | The Regents Of The University Of California | Ketobutyrate compounds and compositions for treating age-related symptoms and diseases |
| KR101633703B1 (ko) * | 2014-12-30 | 2016-06-27 | 한국원자력의학원 | necro X-5를 유효성분으로 포함하는 방사선 조사에 의한 세포손상 예방 또는 치료용 조성물 |
| CN107434819B (zh) * | 2017-02-15 | 2020-03-17 | 河北医科大学第二医院 | 吲哚-tempo缀合物及其在保护远隔器官对抗缺血再灌注损伤中的用途 |
| CN111278807B (zh) | 2017-08-17 | 2022-07-22 | 凯瑞康宁生物工程（武汉）有限公司 | 活性氧清除剂衍生物的制备及用途 |
| CN111356699B (zh) | 2017-09-04 | 2022-08-23 | 凯瑞康宁生物工程（武汉）有限公司 | 活性氧清除剂的制备及用途 |
| KR20200069259A (ko) | 2018-12-06 | 2020-06-16 | 국립암센터 | nc886을 포함하는 암살상 바이러스 활성 증진 또는 생산 증진용 조성물 |
| US11795147B2 (en) | 2019-08-26 | 2023-10-24 | Boehringer Ingelheim International Gmbh | Modulators of complex I |
| US20240009202A1 (en) | 2020-08-19 | 2024-01-11 | Mitoimmune Therapeutics Inc. | Mitochondria-targeted antioxidant as agent for treating pathologic inflammation caused by mabc-r infection |
| US20240043409A1 (en) | 2021-04-12 | 2024-02-08 | Mitoimmune Therapeutics Inc. | Crystalline forms of 5-[(1,1-dioxido-4-thiomorpholinyl)methyl]-2-phenyl-n-(tetrahydro-2h-pyran-4-yl)-1h-indol-7-amine |
| EP4324829A4 (en) | 2021-04-12 | 2025-04-23 | MitoImmune Therapeutics Inc. | 5-[(1,1-DIOXIDO-4-THIOMORPHOLINYL)METHYL]-2-PHENYL-N-(TETRAHYDRO-2H-PYRAN-4-YL)-1H-INDOL-7-AMINE SULFATE AND A NEW CRYSTALLINE FORM THEREOF |
| WO2023182840A1 (ko) * | 2022-03-25 | 2023-09-28 | 주식회사 미토이뮨테라퓨틱스 | 항바이러스용 약학적 조성물 및 이의 용도 |
| DE102023204801A1 (de) * | 2023-05-23 | 2024-11-28 | Continental Reifen Deutschland Gmbh | Verbindung als Alterungsschutzmittel in Kautschukmischungen und Fahrzeugreifen |
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| US6420429B1 (en) * | 1997-12-23 | 2002-07-16 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Brain targeted low molecular weight hydrophobic antioxidant compounds |
| RU2182908C2 (ru) * | 1997-09-05 | 2002-05-27 | Лид Кемикал Ко., Лтд. | Стереоизомерные индольные соединения, способ их получения и их использование |
| EP1133487B1 (en) * | 1998-11-25 | 2004-09-15 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Antioxidants |
| IL130169A (en) * | 1999-05-27 | 2006-08-20 | Neurim Pharma 1991 | Indole derivatives, and pharmaceutical preparations, skin protection preparations, and cosmetics containing them |
| AR039209A1 (es) * | 2002-04-03 | 2005-02-09 | Novartis Ag | Derivados de indolilmaleimida |
| DE10217006A1 (de) * | 2002-04-16 | 2003-11-06 | Merck Patent Gmbh | Substituierte Indole |
| WO2006112549A1 (ja) * | 2005-04-20 | 2006-10-26 | Takeda Pharmaceutical Company Limited | 縮合複素環化合物 |
| JP2008538586A (ja) * | 2005-04-21 | 2008-10-30 | グレン エー． ゴールドスタイン， | 酸化ストレスに関連する疾患および病気の処置のためのｎ−アセチルシステインアミド（ｎａｃアミド） |
| US20070161609A1 (en) * | 2006-01-10 | 2007-07-12 | Charles Buck | Use of mitochondrially targeted antioxidant in treatment and prevention of drug-induced liver disease |
| KR20090018593A (ko) * | 2007-08-17 | 2009-02-20 | 주식회사 엘지생명과학 | 세포괴사 저해제로서의 인돌 및 인다졸 화합물 |
| RU2450001C2 (ru) * | 2007-12-20 | 2012-05-10 | Эл Джи Лайф Сайенсиз Лтд. | Активаторы глюкокиназы и фармацевтические композиции, содержащие их в качестве активного ингредиента |
| WO2009088192A2 (ko) * | 2008-01-04 | 2009-07-16 | Lg Life Sciences Ltd. | 세포, 조직 및 장기 보존 효과를 갖는 인돌 및 인다졸 유도체 |
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| MX338807B (es) | 2016-05-02 |
| TR201204895T1 (tr) | 2013-01-21 |
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| EP2493469A4 (en) | 2013-05-29 |
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| RU2557243C2 (ru) | 2015-07-20 |
| TW201414473A (zh) | 2014-04-16 |
| BR112012009894A2 (pt) | 2016-11-29 |
| KR20110046321A (ko) | 2011-05-04 |
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| JP2013508452A (ja) | 2013-03-07 |
| WO2011052950A2 (en) | 2011-05-05 |
| US20170165272A1 (en) | 2017-06-15 |
| CN102596198A (zh) | 2012-07-18 |
| TWI535440B (zh) | 2016-06-01 |
| US20120214804A1 (en) | 2012-08-23 |
| CN102596198B (zh) | 2016-01-27 |
| KR101325272B1 (ko) | 2013-11-05 |
| WO2011052950A3 (en) | 2011-11-24 |
| US10322135B2 (en) | 2019-06-18 |
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