EA014552B1 - 3,7-диамино-10н-фенотиазиновые соли и их применение - Google Patents
3,7-диамино-10н-фенотиазиновые соли и их применение Download PDFInfo
- Publication number
- EA014552B1 EA014552B1 EA200870384A EA200870384A EA014552B1 EA 014552 B1 EA014552 B1 EA 014552B1 EA 200870384 A EA200870384 A EA 200870384A EA 200870384 A EA200870384 A EA 200870384A EA 014552 B1 EA014552 B1 EA 014552B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- compound according
- compound
- independently
- compounds
- groups
- Prior art date
Links
- LZILOGCFZJDPTG-UHFFFAOYSA-N 10h-phenothiazine-3,7-diamine Chemical class C1=C(N)C=C2SC3=CC(N)=CC=C3NC2=C1 LZILOGCFZJDPTG-UHFFFAOYSA-N 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 224
- 150000003839 salts Chemical class 0.000 claims abstract description 43
- 238000011282 treatment Methods 0.000 claims abstract description 38
- 239000003814 drug Substances 0.000 claims abstract description 34
- 239000002253 acid Substances 0.000 claims abstract description 15
- 239000012453 solvate Substances 0.000 claims abstract description 12
- 208000034799 Tauopathies Diseases 0.000 claims abstract description 11
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 9
- 150000004677 hydrates Chemical class 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 61
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 49
- 201000010099 disease Diseases 0.000 claims description 48
- 108090000623 proteins and genes Proteins 0.000 claims description 32
- 102000004169 proteins and genes Human genes 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 230000004845 protein aggregation Effects 0.000 claims description 27
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 239000003085 diluting agent Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000003937 drug carrier Substances 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 230000002401 inhibitory effect Effects 0.000 claims description 10
- 230000002265 prevention Effects 0.000 claims description 10
- 238000002560 therapeutic procedure Methods 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 201000004792 malaria Diseases 0.000 claims description 8
- 229910052700 potassium Inorganic materials 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 208000005176 Hepatitis C Diseases 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 5
- 241000710886 West Nile virus Species 0.000 claims description 5
- 201000001441 melanoma Diseases 0.000 claims description 5
- 230000000626 neurodegenerative effect Effects 0.000 claims description 5
- 244000052769 pathogen Species 0.000 claims description 5
- 230000003612 virological effect Effects 0.000 claims description 5
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 4
- 208000000453 Skin Neoplasms Diseases 0.000 claims description 4
- 230000001580 bacterial effect Effects 0.000 claims description 4
- 201000000849 skin cancer Diseases 0.000 claims description 4
- 230000000415 inactivating effect Effects 0.000 claims description 3
- 241000711549 Hepacivirus C Species 0.000 claims description 2
- 230000001717 pathogenic effect Effects 0.000 claims description 2
- 208000030381 cutaneous melanoma Diseases 0.000 claims 2
- 201000003708 skin melanoma Diseases 0.000 claims 2
- 230000002829 reductive effect Effects 0.000 abstract description 28
- 229940079593 drug Drugs 0.000 abstract description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 4
- 150000002990 phenothiazines Chemical class 0.000 abstract description 4
- 239000000651 prodrug Substances 0.000 abstract description 4
- 229940002612 prodrug Drugs 0.000 abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 87
- 239000000203 mixture Substances 0.000 description 74
- 230000015572 biosynthetic process Effects 0.000 description 62
- 108010026424 tau Proteins Proteins 0.000 description 61
- 102000013498 tau Proteins Human genes 0.000 description 61
- 125000003277 amino group Chemical group 0.000 description 53
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 51
- 238000003786 synthesis reaction Methods 0.000 description 36
- 239000007787 solid Substances 0.000 description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
- -1 10H-phenothiazine compound Chemical class 0.000 description 28
- 239000000243 solution Substances 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- 230000000875 corresponding effect Effects 0.000 description 21
- 230000002776 aggregation Effects 0.000 description 20
- 238000004220 aggregation Methods 0.000 description 20
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 20
- 239000002244 precipitate Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000007864 aqueous solution Substances 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000012634 fragment Substances 0.000 description 15
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 15
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 14
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- 230000009467 reduction Effects 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- JEOGFTYLESYHAM-UHFFFAOYSA-N 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]ethanone Chemical compound C1=C(N(C)C)C=C2SC3=CC(N(C)C)=CC=C3N(C(C)=O)C2=C1 JEOGFTYLESYHAM-UHFFFAOYSA-N 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 12
- 238000010511 deprotection reaction Methods 0.000 description 12
- 230000035772 mutation Effects 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 11
- 206010012289 Dementia Diseases 0.000 description 10
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 10
- 239000005457 ice water Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000001575 pathological effect Effects 0.000 description 9
- 101150072179 ATP1 gene Proteins 0.000 description 8
- 101100003366 Arabidopsis thaliana ATPA gene Proteins 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 102100021649 Elongator complex protein 6 Human genes 0.000 description 8
- 101100065219 Homo sapiens ELP6 gene Proteins 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 101150105046 atpI gene Proteins 0.000 description 8
- 210000004369 blood Anatomy 0.000 description 8
- 239000008280 blood Substances 0.000 description 8
- 238000009826 distribution Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000003446 ligand Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- 239000000546 pharmaceutical excipient Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 7
- SVGWCDNHRGNKAU-UHFFFAOYSA-N 2-methylthionin-1-ium;chloride;trihydrate Chemical compound O.O.O.[Cl-].CC1=CC=CC=CC=C[SH+]1 SVGWCDNHRGNKAU-UHFFFAOYSA-N 0.000 description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000013058 crude material Substances 0.000 description 7
- 239000002552 dosage form Substances 0.000 description 7
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 235000010288 sodium nitrite Nutrition 0.000 description 7
- 238000006467 substitution reaction Methods 0.000 description 7
- 230000001225 therapeutic effect Effects 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 206010002022 amyloidosis Diseases 0.000 description 6
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 210000000936 intestine Anatomy 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 101000587820 Homo sapiens Selenide, water dikinase 1 Proteins 0.000 description 5
- 101000701815 Homo sapiens Spermidine synthase Proteins 0.000 description 5
- 102100031163 Selenide, water dikinase 1 Human genes 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- 229960000907 methylthioninium chloride Drugs 0.000 description 5
- 230000004770 neurodegeneration Effects 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 230000009885 systemic effect Effects 0.000 description 5
- ILRSRMBVKMECCY-UHFFFAOYSA-N 1-[3,7-bis(diethylamino)phenothiazin-10-yl]ethanone Chemical compound C1=C(N(CC)CC)C=C2SC3=CC(N(CC)CC)=CC=C3N(C(C)=O)C2=C1 ILRSRMBVKMECCY-UHFFFAOYSA-N 0.000 description 4
- KPYHKEZPEDJERZ-UHFFFAOYSA-N 10h-phenothiazine-1,2-diamine Chemical class C1=CC=C2NC3=C(N)C(N)=CC=C3SC2=C1 KPYHKEZPEDJERZ-UHFFFAOYSA-N 0.000 description 4
- KCSURCKZGJUTCH-UHFFFAOYSA-N 3,7-dinitro-10h-phenothiazine Chemical compound C1=C([N+]([O-])=O)C=C2SC3=CC([N+](=O)[O-])=CC=C3NC2=C1 KCSURCKZGJUTCH-UHFFFAOYSA-N 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
- 102000013455 Amyloid beta-Peptides Human genes 0.000 description 4
- 108010090849 Amyloid beta-Peptides Proteins 0.000 description 4
- 241000282693 Cercopithecidae Species 0.000 description 4
- 208000027089 Parkinsonian disease Diseases 0.000 description 4
- 206010034010 Parkinsonism Diseases 0.000 description 4
- 102000019355 Synuclein Human genes 0.000 description 4
- 108050006783 Synuclein Proteins 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 210000004556 brain Anatomy 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000007850 degeneration Effects 0.000 description 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 4
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 4
- 238000002372 labelling Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 208000015122 neurodegenerative disease Diseases 0.000 description 4
- 238000006396 nitration reaction Methods 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 229950000688 phenothiazine Drugs 0.000 description 4
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 4
- 229940067157 phenylhydrazine Drugs 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 208000011580 syndromic disease Diseases 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- FCOLCILVZULVQA-UHFFFAOYSA-N 1-(3,7-diaminophenothiazin-10-yl)ethanone Chemical compound NC1=CC=C2N(C(=O)C)C3=CC=C(N)C=C3SC2=C1 FCOLCILVZULVQA-UHFFFAOYSA-N 0.000 description 3
- CLXYGCPNHLXLPD-UHFFFAOYSA-N 3-nitro-10h-phenothiazine Chemical compound C1=CC=C2SC3=CC([N+](=O)[O-])=CC=C3NC2=C1 CLXYGCPNHLXLPD-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 206010003694 Atrophy Diseases 0.000 description 3
- 108020004414 DNA Proteins 0.000 description 3
- 101000979001 Homo sapiens Methionine aminopeptidase 2 Proteins 0.000 description 3
- 101000969087 Homo sapiens Microtubule-associated protein 2 Proteins 0.000 description 3
- 102100033468 Lysozyme C Human genes 0.000 description 3
- 102100023174 Methionine aminopeptidase 2 Human genes 0.000 description 3
- 241000288906 Primates Species 0.000 description 3
- 102000029797 Prion Human genes 0.000 description 3
- 108091000054 Prion Proteins 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 3
- 241000700605 Viruses Species 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000037444 atrophy Effects 0.000 description 3
- 210000000349 chromosome Anatomy 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000003745 diagnosis Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 3
- 150000002496 iodine Chemical class 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 150000007523 nucleic acids Chemical class 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 230000002797 proteolythic effect Effects 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- PVPBBTJXIKFICP-UHFFFAOYSA-N (7-aminophenothiazin-3-ylidene)azanium;chloride Chemical compound [Cl-].C1=CC(=[NH2+])C=C2SC3=CC(N)=CC=C3N=C21 PVPBBTJXIKFICP-UHFFFAOYSA-N 0.000 description 2
- SCRNYDIZOWXHBQ-UHFFFAOYSA-N (7-azaniumyl-10h-phenothiazin-3-yl)azanium;dichloride Chemical compound [Cl-].[Cl-].C1=C([NH3+])C=C2SC3=CC([NH3+])=CC=C3NC2=C1 SCRNYDIZOWXHBQ-UHFFFAOYSA-N 0.000 description 2
- VUWDHXCPXJCIJQ-UHFFFAOYSA-N 1-(3,7-dinitrophenothiazin-10-yl)ethanone Chemical compound [O-][N+](=O)C1=CC=C2N(C(=O)C)C3=CC=C([N+]([O-])=O)C=C3SC2=C1 VUWDHXCPXJCIJQ-UHFFFAOYSA-N 0.000 description 2
- 102100027831 14-3-3 protein theta Human genes 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- 206010007134 Candida infections Diseases 0.000 description 2
- 206010010356 Congenital anomaly Diseases 0.000 description 2
- 206010012735 Diarrhoea Diseases 0.000 description 2
- 241000283073 Equus caballus Species 0.000 description 2
- 108010049003 Fibrinogen Proteins 0.000 description 2
- 102000008946 Fibrinogen Human genes 0.000 description 2
- 206010016654 Fibrosis Diseases 0.000 description 2
- 201000011240 Frontotemporal dementia Diseases 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 102000004877 Insulin Human genes 0.000 description 2
- 108090001061 Insulin Proteins 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 102000029749 Microtubule Human genes 0.000 description 2
- 108091022875 Microtubule Proteins 0.000 description 2
- 108010014251 Muramidase Proteins 0.000 description 2
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- 108010071690 Prealbumin Proteins 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 102000009190 Transthyretin Human genes 0.000 description 2
- JAUPSVVTGFBHTN-UHFFFAOYSA-N [7-(dimethylazaniumyl)-10h-phenothiazin-3-yl]-dimethylazanium;dibromide Chemical compound [Br-].[Br-].C1=C([NH+](C)C)C=C2SC3=CC([NH+](C)C)=CC=C3NC2=C1 JAUPSVVTGFBHTN-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000004931 aggregating effect Effects 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 230000000890 antigenic effect Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 102000003799 beta-Synuclein Human genes 0.000 description 2
- 108090000182 beta-Synuclein Proteins 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 210000004899 c-terminal region Anatomy 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000002490 cerebral effect Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000007882 cirrhosis Effects 0.000 description 2
- 208000019425 cirrhosis of liver Diseases 0.000 description 2
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000000306 component Substances 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000034994 death Effects 0.000 description 2
- 231100000517 death Toxicity 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 230000006806 disease prevention Effects 0.000 description 2
- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 description 2
- 210000003743 erythrocyte Anatomy 0.000 description 2
- 210000003754 fetus Anatomy 0.000 description 2
- 229940012952 fibrinogen Drugs 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 229940125396 insulin Drugs 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 230000003834 intracellular effect Effects 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 2
- 150000004694 iodide salts Chemical group 0.000 description 2
- QTWZICCBKBYHDM-UHFFFAOYSA-N leucomethylene blue Chemical compound C1=C(N(C)C)C=C2SC3=CC(N(C)C)=CC=C3NC2=C1 QTWZICCBKBYHDM-UHFFFAOYSA-N 0.000 description 2
- 239000004325 lysozyme Substances 0.000 description 2
- 229960000274 lysozyme Drugs 0.000 description 2
- 235000010335 lysozyme Nutrition 0.000 description 2
- 210000005171 mammalian brain Anatomy 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 210000004379 membrane Anatomy 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 210000004688 microtubule Anatomy 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 108020004707 nucleic acids Proteins 0.000 description 2
- 102000039446 nucleic acids Human genes 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000000069 prophylactic effect Effects 0.000 description 2
- 230000017854 proteolysis Effects 0.000 description 2
- 230000010076 replication Effects 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- 231100001274 therapeutic index Toxicity 0.000 description 2
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 2
- 238000002054 transplantation Methods 0.000 description 2
- 238000011269 treatment regimen Methods 0.000 description 2
- XEEQGYMUWCZPDN-DOMZBBRYSA-N (-)-(11S,2'R)-erythro-mefloquine Chemical compound C([C@@H]1[C@@H](O)C=2C3=CC=CC(=C3N=C(C=2)C(F)(F)F)C(F)(F)F)CCCN1 XEEQGYMUWCZPDN-DOMZBBRYSA-N 0.000 description 1
- UOGZWWISWPADQM-SDVXZCCESA-N (1r,2r,3r,4s,6s)-2,3,6-trichloro-4,7-bis(dichloromethyl)-7-methylbicyclo[2.2.1]heptane Chemical compound Cl[C@H]1C[C@@]2(C(Cl)Cl)[C@@H](Cl)[C@H](Cl)[C@@H]1C2(C(Cl)Cl)C UOGZWWISWPADQM-SDVXZCCESA-N 0.000 description 1
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 1
- IGQIUOIGQKMPLI-UHFFFAOYSA-N 1-[3,7-bis(ethylamino)phenothiazin-10-yl]ethanone Chemical compound C1=C(NCC)C=C2SC3=CC(NCC)=CC=C3N(C(C)=O)C2=C1 IGQIUOIGQKMPLI-UHFFFAOYSA-N 0.000 description 1
- SARMGXPVOFNNNG-UHFFFAOYSA-N 1-[amino-(4-chloroanilino)methylidene]-2-propan-2-ylguanidine;hydron;chloride Chemical compound Cl.CC(C)N=C(N)N=C(N)NC1=CC=C(Cl)C=C1 SARMGXPVOFNNNG-UHFFFAOYSA-N 0.000 description 1
- WOGWYSWDBYCVDY-UHFFFAOYSA-N 2-chlorocyclohexa-2,5-diene-1,4-dione Chemical compound ClC1=CC(=O)C=CC1=O WOGWYSWDBYCVDY-UHFFFAOYSA-N 0.000 description 1
- DNECCZDSSLSZQV-UHFFFAOYSA-N 2-methylthionin-1-ium;iodide Chemical compound [I-].CC1=CC=CC=CC=C[SH+]1 DNECCZDSSLSZQV-UHFFFAOYSA-N 0.000 description 1
- GJOHLWZHWQUKAU-UHFFFAOYSA-N 5-azaniumylpentan-2-yl-(6-methoxyquinolin-8-yl)azanium;dihydrogen phosphate Chemical compound OP(O)(O)=O.OP(O)(O)=O.N1=CC=CC2=CC(OC)=CC(NC(C)CCCN)=C21 GJOHLWZHWQUKAU-UHFFFAOYSA-N 0.000 description 1
- 208000023769 AA amyloidosis Diseases 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000037259 Amyloid Plaque Diseases 0.000 description 1
- 108010079054 Amyloid beta-Protein Precursor Proteins 0.000 description 1
- 102000014303 Amyloid beta-Protein Precursor Human genes 0.000 description 1
- 206010002025 Amyloidosis senile Diseases 0.000 description 1
- 102100032187 Androgen receptor Human genes 0.000 description 1
- 208000028185 Angioedema Diseases 0.000 description 1
- 102000007592 Apolipoproteins Human genes 0.000 description 1
- 108010071619 Apolipoproteins Proteins 0.000 description 1
- 206010003591 Ataxia Diseases 0.000 description 1
- 102000014461 Ataxins Human genes 0.000 description 1
- 108010078286 Ataxins Proteins 0.000 description 1
- 101800001288 Atrial natriuretic factor Proteins 0.000 description 1
- 102400001282 Atrial natriuretic peptide Human genes 0.000 description 1
- 101800001890 Atrial natriuretic peptide Proteins 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 208000024806 Brain atrophy Diseases 0.000 description 1
- 208000014644 Brain disease Diseases 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 201000007120 C1 inhibitor deficiency Diseases 0.000 description 1
- ZZHCQLRXAWWKNO-UHFFFAOYSA-N C1=CC=CSC=CC=C1.I Chemical compound C1=CC=CSC=CC=C1.I ZZHCQLRXAWWKNO-UHFFFAOYSA-N 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 208000006154 Chronic hepatitis C Diseases 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- 108091029433 Conserved non-coding sequence Proteins 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- 102000012192 Cystatin C Human genes 0.000 description 1
- 108010061642 Cystatin C Proteins 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 206010013142 Disinhibition Diseases 0.000 description 1
- 201000010374 Down Syndrome Diseases 0.000 description 1
- 102000013138 Drug Receptors Human genes 0.000 description 1
- 108010065556 Drug Receptors Proteins 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 206010014561 Emphysema Diseases 0.000 description 1
- 208000032274 Encephalopathy Diseases 0.000 description 1
- 241000792859 Enema Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000289695 Eutheria Species 0.000 description 1
- 206010016202 Familial Amyloidosis Diseases 0.000 description 1
- 241000282324 Felis Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 102000004878 Gelsolin Human genes 0.000 description 1
- 108090001064 Gelsolin Proteins 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 241000282575 Gorilla Species 0.000 description 1
- 206010018910 Haemolysis Diseases 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 102100021519 Hemoglobin subunit beta Human genes 0.000 description 1
- 108091005904 Hemoglobin subunit beta Proteins 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 206010019860 Hereditary angioedema Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 101001018100 Homo sapiens Lysozyme C Proteins 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 241000282620 Hylobates sp. Species 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010022004 Influenza like illness Diseases 0.000 description 1
- 208000000913 Kidney Calculi Diseases 0.000 description 1
- 102000003855 L-lactate dehydrogenase Human genes 0.000 description 1
- 108700023483 L-lactate dehydrogenases Proteins 0.000 description 1
- 102000009664 Microtubule-Associated Proteins Human genes 0.000 description 1
- 108010020004 Microtubule-Associated Proteins Proteins 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 1
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 1
- 208000010428 Muscle Weakness Diseases 0.000 description 1
- 206010028289 Muscle atrophy Diseases 0.000 description 1
- 206010028372 Muscular weakness Diseases 0.000 description 1
- 206010029148 Nephrolithiasis Diseases 0.000 description 1
- 102100037591 Neuroserpin Human genes 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000282577 Pan troglodytes Species 0.000 description 1
- 241001504519 Papio ursinus Species 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 208000037273 Pathologic Processes Diseases 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 241000282405 Pongo abelii Species 0.000 description 1
- 102000015499 Presenilins Human genes 0.000 description 1
- 108010050254 Presenilins Proteins 0.000 description 1
- 208000024777 Prion disease Diseases 0.000 description 1
- 108010048233 Procalcitonin Proteins 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 102000001708 Protein Isoforms Human genes 0.000 description 1
- 108010029485 Protein Isoforms Proteins 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010038357 Renal amyloidosis Diseases 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 239000008156 Ringer's lactate solution Substances 0.000 description 1
- XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 102000008847 Serpin Human genes 0.000 description 1
- 108050000761 Serpin Proteins 0.000 description 1
- 102000054727 Serum Amyloid A Human genes 0.000 description 1
- 108700028909 Serum Amyloid A Proteins 0.000 description 1
- 102000019197 Superoxide Dismutase Human genes 0.000 description 1
- 108010012715 Superoxide dismutase Proteins 0.000 description 1
- 229940122777 Tau aggregation inhibitor Drugs 0.000 description 1
- 208000001435 Thromboembolism Diseases 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 102000004243 Tubulin Human genes 0.000 description 1
- 108090000704 Tubulin Proteins 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- QFHKZASDZUVDPT-UHFFFAOYSA-N [Cl-].CCC1=CC=CC=CC=C[SH+]1 Chemical compound [Cl-].CCC1=CC=CC=CC=C[SH+]1 QFHKZASDZUVDPT-UHFFFAOYSA-N 0.000 description 1
- NDEQAARTTAIOLN-UHFFFAOYSA-M [I-].[Na+].CI Chemical compound [I-].[Na+].CI NDEQAARTTAIOLN-UHFFFAOYSA-M 0.000 description 1
- 230000001594 aberrant effect Effects 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 238000001467 acupuncture Methods 0.000 description 1
- 231100000354 acute hepatitis Toxicity 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 102000003802 alpha-Synuclein Human genes 0.000 description 1
- 108090000185 alpha-Synuclein Proteins 0.000 description 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
- 108010080146 androgen receptors Proteins 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000004019 antithrombin Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229940106943 azor Drugs 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 239000012503 blood component Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical group N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 description 1
- ZEWYCNBZMPELPF-UHFFFAOYSA-J calcium;potassium;sodium;2-hydroxypropanoic acid;sodium;tetrachloride Chemical compound [Na].[Na+].[Cl-].[Cl-].[Cl-].[Cl-].[K+].[Ca+2].CC(O)C(O)=O ZEWYCNBZMPELPF-UHFFFAOYSA-J 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- NSQLIUXCMFBZME-MPVJKSABSA-N carperitide Chemical compound C([C@H]1C(=O)NCC(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CSSC[C@@H](C(=O)N1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(O)=O)=O)[C@@H](C)CC)C1=CC=CC=C1 NSQLIUXCMFBZME-MPVJKSABSA-N 0.000 description 1
- 238000000423 cell based assay Methods 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000007541 cellular toxicity Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 210000003710 cerebral cortex Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229960003677 chloroquine Drugs 0.000 description 1
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 1
- 239000000544 cholinesterase inhibitor Substances 0.000 description 1
- 208000037976 chronic inflammation Diseases 0.000 description 1
- 208000037893 chronic inflammatory disorder Diseases 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000011284 combination treatment Methods 0.000 description 1
- 238000000750 constant-initial-state spectroscopy Methods 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000001054 cortical effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 230000004452 decreased vision Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 210000001947 dentate gyrus Anatomy 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 229940039227 diagnostic agent Drugs 0.000 description 1
- 239000000032 diagnostic agent Substances 0.000 description 1
- NSNHWTBQMQIDCF-UHFFFAOYSA-N dihydrate;hydrochloride Chemical compound O.O.Cl NSNHWTBQMQIDCF-UHFFFAOYSA-N 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 229960003530 donepezil Drugs 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 229960003722 doxycycline Drugs 0.000 description 1
- XQTWDDCIUJNLTR-CVHRZJFOSA-N doxycycline monohydrate Chemical compound O.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@@H]1[C@H]2O XQTWDDCIUJNLTR-CVHRZJFOSA-N 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000007920 enema Substances 0.000 description 1
- 229940095399 enema Drugs 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 201000007891 familial visceral amyloidosis Diseases 0.000 description 1
- 230000002600 fibrillogenic effect Effects 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 229960003980 galantamine Drugs 0.000 description 1
- ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000001415 gene therapy Methods 0.000 description 1
- 230000005182 global health Effects 0.000 description 1
- 125000000404 glutamine group Chemical group N[C@@H](CCC(N)=O)C(=O)* 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000001631 haemodialysis Methods 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000003862 health status Effects 0.000 description 1
- 230000000322 hemodialysis Effects 0.000 description 1
- 230000008588 hemolysis Effects 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 208000010710 hepatitis C virus infection Diseases 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000009169 immunotherapy Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000000138 intercalating agent Substances 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])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])C([H])([H])[H] 0.000 description 1
- 235000021190 leftovers Nutrition 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 229960001962 mefloquine Drugs 0.000 description 1
- 229960004640 memantine Drugs 0.000 description 1
- LDDHMLJTFXJGPI-UHFFFAOYSA-N memantine hydrochloride Chemical compound Cl.C1C(C2)CC3(C)CC1(C)CC2(N)C3 LDDHMLJTFXJGPI-UHFFFAOYSA-N 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 208000005135 methemoglobinemia Diseases 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 230000020763 muscle atrophy Effects 0.000 description 1
- 201000000585 muscular atrophy Diseases 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 239000007783 nanoporous material Substances 0.000 description 1
- 229940097496 nasal spray Drugs 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 210000002682 neurofibrillary tangle Anatomy 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 108010080874 neuroserpin Proteins 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 231100000862 numbness Toxicity 0.000 description 1
- 229960000988 nystatin Drugs 0.000 description 1
- VQOXZBDYSJBXMA-NQTDYLQESA-N nystatin A1 Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 VQOXZBDYSJBXMA-NQTDYLQESA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000009054 pathological process Effects 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 238000002428 photodynamic therapy Methods 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 210000004180 plasmocyte Anatomy 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 238000002600 positron emission tomography Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 229960005179 primaquine Drugs 0.000 description 1
- CWCXERYKLSEGEZ-KDKHKZEGSA-N procalcitonin Chemical compound C([C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H](C(=O)N[C@@H](C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)NCC(O)=O)[C@@H](C)O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCSC)NC(=O)[C@H]1NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@@H](N)CSSC1)[C@@H](C)O)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 CWCXERYKLSEGEZ-KDKHKZEGSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000004393 prognosis Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 201000002212 progressive supranuclear palsy Diseases 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 229960001870 proguanil hydrochloride Drugs 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 230000006337 proteolytic cleavage Effects 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 210000002763 pyramidal cell Anatomy 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002824 redox indicator Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 229960004136 rivastigmine Drugs 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 102200036626 rs104893877 Human genes 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003001 serine protease inhibitor Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000008354 sodium chloride injection Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- KUUVQVSHGLHAKZ-UHFFFAOYSA-N thionine Chemical compound C=1C=CC=CSC=CC=1 KUUVQVSHGLHAKZ-UHFFFAOYSA-N 0.000 description 1
- 150000000552 thionines Chemical class 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 239000000083 urinary anti-infective agent Substances 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 244000052613 viral pathogen Species 0.000 description 1
- 230000003253 viricidal effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/5415—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with carbocyclic ring systems, e.g. phenothiazine, chlorpromazine, piroxicam
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/20—[b, e]-condensed with two six-membered rings with hydrogen atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B21/00—Thiazine dyes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Virology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Molecular Biology (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- AIDS & HIV (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Obesity (AREA)
- Rheumatology (AREA)
- Anesthesiology (AREA)
- Cardiology (AREA)
- Gastroenterology & Hepatology (AREA)
- Emergency Medicine (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78669006P | 2006-03-29 | 2006-03-29 | |
| PCT/GB2007/001103 WO2007110627A2 (en) | 2006-03-29 | 2007-03-28 | 3,7-diamino-10h-phenothiazine salts and their use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200870384A1 EA200870384A1 (ru) | 2009-04-28 |
| EA014552B1 true EA014552B1 (ru) | 2010-12-30 |
Family
ID=38421429
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200870384A EA014552B1 (ru) | 2006-03-29 | 2007-03-28 | 3,7-диамино-10н-фенотиазиновые соли и их применение |
Country Status (18)
| Country | Link |
|---|---|
| US (5) | US7888350B2 (enExample) |
| EP (1) | EP2013191B3 (enExample) |
| JP (3) | JP5520043B2 (enExample) |
| KR (1) | KR100983301B1 (enExample) |
| CN (5) | CN104529939B (enExample) |
| AT (1) | ATE478058T3 (enExample) |
| AU (1) | AU2007231124B2 (enExample) |
| CA (1) | CA2646163C (enExample) |
| DE (1) | DE602007008550D1 (enExample) |
| DK (1) | DK2013191T6 (enExample) |
| EA (1) | EA014552B1 (enExample) |
| ES (1) | ES2349322T7 (enExample) |
| HR (1) | HRP20100614T4 (enExample) |
| IL (2) | IL194516A (enExample) |
| MY (1) | MY143757A (enExample) |
| PL (1) | PL2013191T6 (enExample) |
| PT (1) | PT2013191E (enExample) |
| WO (1) | WO2007110627A2 (enExample) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101084204B (zh) | 2004-09-23 | 2012-12-05 | 卫思道制药有限公司 | 包括亚甲蓝(mtc)在内的二氨基吩噻嗪鎓化合物的化学合成和纯化方法 |
| DE602007008550D1 (de) | 2006-03-29 | 2010-09-30 | Wista Lab Ltd | 3,7-diamino-10h-phenothiazinsalze und ihre verwendung |
| AU2007231126B2 (en) | 2006-03-29 | 2012-11-01 | TauRx Therapeutics Management Ltd | Inhibitors of protein aggregation |
| US7956183B2 (en) | 2006-07-11 | 2011-06-07 | Wista Laboratories Ltd. | Methods of synthesis and/or purification of diaminophenothiazinium compounds |
| CA2686513C (en) * | 2007-04-03 | 2017-06-13 | Prosetta Bioconformatics Inc. | Diamino-benzothiazine derivatives as antiviral agents |
| PL2167095T3 (pl) * | 2007-06-19 | 2019-11-29 | Wista Lab Ltd | Związki fenotiazynowe do leczenia łagodnych zaburzeń poznawczych |
| FR2920775B1 (fr) | 2007-09-07 | 2009-11-06 | Pharma Hydro Dev P H D Soc Par | Nouveaux composes diaminophenothiazine, leur procede de preparation et leurs utilisations. |
| MY161656A (en) * | 2007-10-03 | 2017-04-28 | Wista Lab Ltd | Therapeutic use of diaminophenothiazines |
| PL3112358T3 (pl) * | 2008-12-10 | 2020-11-16 | Wista Laboratories Ltd. | 3,6-Dipodstawione sole ksantyliowe |
| EP3378856B1 (en) * | 2009-09-24 | 2020-12-02 | WisTa Laboratories Ltd. | Crystalline methylthioninium chloride hydrates |
| ES2659091T3 (es) | 2009-09-24 | 2018-03-13 | Wista Laboratories Ltd. | Pentahidrato de cloruro de metiltioninio, preparación y uso farmacéutico del mismo |
| US8828986B2 (en) | 2011-04-20 | 2014-09-09 | Prosetta Antiviral Inc. | Antiviral compounds |
| US8785434B2 (en) | 2010-04-30 | 2014-07-22 | Prosetta Antiviral Inc. | Antiviral compounds |
| CN103379901B (zh) | 2010-11-30 | 2018-04-03 | 维斯塔实验室有限公司 | 含有氯化甲基息奥宁的配方 |
| ES2714692T3 (es) | 2011-01-31 | 2019-05-29 | Tau Bio Logic Corp | Tratamiento de tauopatías |
| RS55237B1 (sr) | 2011-02-11 | 2017-02-28 | Wis Ta Laboratories Ltd | Fenotiazin diaminijum soli i njihova primena |
| US20130315825A1 (en) * | 2012-05-03 | 2013-11-28 | Washington University | Tricyclic heteroaromatic compounds as alpha-synuclein ligands |
| GB201512678D0 (en) * | 2015-07-20 | 2015-08-26 | Wista Lab Ltd | Methods of chemical synthesis |
| CN105541756B (zh) * | 2015-12-17 | 2018-02-09 | 陕西方舟制药有限公司 | 一种制备1‑(3,7‑双二甲氨基‑吩噻嗪‑10‑基)乙酮的方法 |
| ITUA20163526A1 (it) * | 2016-05-17 | 2017-11-17 | Icrom Spa | Procedimento per la preparazione di composti diamminofenotiazinici ad elevato grado di purezza |
| KR102475825B1 (ko) * | 2016-07-25 | 2022-12-08 | 위스타 레보레이토리스 리미티드 | 디아미노페노티아진 (diaminophenothiazines)의 투여 및 투여량 (dosage) |
| GB201614834D0 (en) * | 2016-09-01 | 2016-10-19 | Wista Lab Ltd | Treatment of dementia |
| GB201621817D0 (en) * | 2016-12-21 | 2017-02-01 | Wista Lab Ltd | Methods of chemical synthesis |
| CN107253936B (zh) * | 2017-06-23 | 2021-07-23 | 复旦大学 | 一类可用于次氯酸检测的荧光探针及其制备方法和应用 |
| CN108129418A (zh) * | 2017-12-22 | 2018-06-08 | 郑州大学 | 吩噻嗪-氨基二硫代甲酸酯衍生物及其制备方法和应用 |
| EP4364801B1 (en) | 2018-07-26 | 2025-11-12 | TauRx Therapeutics Management Ltd. | Optimised dosage of diaminophenothiazines in populations |
| CA3111000A1 (en) | 2018-09-05 | 2020-03-12 | Genting Taurx Diagnostic Centre Sdn Bhd | Network methods for neurodegenerative diseases |
| CN109223800A (zh) * | 2018-10-26 | 2019-01-18 | 辽宁大学 | 3,7-二对甲苯胺基-吩噻嗪-5-鎓碘化物与超声协同在抑制肿瘤细胞增殖中的应用 |
| CA3135170A1 (en) | 2019-04-05 | 2020-10-08 | Tauc3 Biologics Limited | Anti-tauc3 antibodies and uses thereof |
| GB201909454D0 (en) | 2019-07-01 | 2019-08-14 | Wista Lab Ltd | Enhancers |
| GB201909493D0 (en) | 2019-07-01 | 2019-08-14 | Wista Lab Ltd | Therapeutic interactions |
| GB201909506D0 (en) | 2019-07-02 | 2019-08-14 | Wista Lab Ltd | Synaptopathies |
| GB202006659D0 (en) | 2020-05-05 | 2020-06-17 | Wista Lab Ltd | Therapeutic treatments |
| CN116056724A (zh) | 2020-05-05 | 2023-05-02 | 维斯塔实验室有限公司 | 用于治疗covid-19的甲基硫堇鎓化合物 |
| MX2022013884A (es) | 2020-05-05 | 2022-11-30 | Wista Lab Ltd | Compuestos de metiltioninio para usarse en el tratamiento de hipoxemia. |
| GB202010652D0 (en) | 2020-07-10 | 2020-08-26 | Wista Lab Ltd | Anti-tau antibodies |
| DE102020212508A1 (de) * | 2020-10-02 | 2022-04-07 | Continental Reifen Deutschland Gmbh | Verbindung, Kautschukmischung enthaltend die Verbindung, Fahrzeugreifen, der die Kautschukmischung in wenigstens einem Bauteil aufweist, Verfahren zur Herstellung der Verbindung sowie Verwendung der Verbindung als Alterungsschutzmittel und/oder Antioxidationsmittel und/oder Antiozonant und/oder Farbstoff |
| GB202204185D0 (en) | 2022-03-24 | 2022-05-11 | Wista Lab Ltd | Oral treatment |
| CA3257856A1 (en) | 2022-05-31 | 2023-12-07 | Wista Lab Ltd | TREATMENT OF NEURODEGENERATIVE DISORDERS USING COMPOUNDS CONTAINING METHYLTHIONINIUM (MT) |
| CN120225180A (zh) | 2022-09-21 | 2025-06-27 | 维斯塔实验室有限公司 | 新型制剂及媒剂 |
| US12410394B2 (en) | 2023-01-06 | 2025-09-09 | Athergen, Inc. | Composition comprising nicotinamide mononucleotide and leucomethylene blue |
| KR20250154422A (ko) | 2023-03-03 | 2025-10-28 | 타우알엑스 쎄라퓨틱스 매니지먼트 리미티드 | 미세혈관 뇌질환 치료를 위한 디아미노페노티아진 |
| CN117447421A (zh) * | 2023-10-30 | 2024-01-26 | 上海沃凯生物技术有限公司 | 一种3,7-双-(二甲胺基)-吩噻嗪的合成方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5220009A (en) * | 1990-05-03 | 1993-06-15 | Yeda Research And Development Company Limited | Phenothiazinium salts and their use for disinfecting aqueous effluents |
| WO1996030766A1 (en) * | 1995-03-27 | 1996-10-03 | F. Hoffmann-La Roche Ag | Inhibition of tau-tau-association |
| WO2002055720A2 (en) * | 2001-01-15 | 2002-07-18 | Univ Aberdeen | Materials and methods relating to protein aggregation in neurodegenerative disease |
Family Cites Families (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE569430A (enExample) * | 1957-07-17 | |||
| US3641016A (en) * | 1968-02-16 | 1972-02-08 | Egyt Gyogyszervegyeszeti Gyar | Thionine derivatives |
| JPS52105931A (en) * | 1976-03-02 | 1977-09-06 | Mita Industrial Co Ltd | New leuco coloring matters and process for manufacture thereof |
| US4309255A (en) | 1980-09-10 | 1982-01-05 | International Business Machines Corporation | Electrochromic recording paper |
| US4647525A (en) * | 1984-10-01 | 1987-03-03 | Minnesota Mining And Manufacturing Company | Stabilized leuco phenazine dyes and their use in an imaging system |
| US4622395A (en) * | 1984-10-01 | 1986-11-11 | Minnesota Mining And Manufacturing Company | Phenoxazine and phenothiazine dyes and leuco forms thereof |
| GB8724412D0 (en) | 1987-10-19 | 1987-11-25 | Medical Res Council | Protein |
| US5571666A (en) * | 1988-10-28 | 1996-11-05 | Oklahoma Medical Research Foundation | Thiazine dyes used to inactivate HIV in biological fluids |
| CA2011116C (en) * | 1989-03-06 | 1999-11-16 | Murray A. Kaplan | Lyophilized bmy-28142 dihydrochloride for parenteral use |
| JPH0725786A (ja) | 1990-05-16 | 1995-01-27 | Univ Rockefeller | アルツハイマー病を伴うアミロイドーシスの治療 |
| AU2414092A (en) | 1991-08-01 | 1993-03-02 | Paul H. Voorheis | Diagnostic method for alzheimer's disease |
| WO1993003177A1 (en) | 1991-08-09 | 1993-02-18 | Massachusetts Institute Of Technology | Novel tau/neurofilament protein kinases |
| DE4140192C2 (de) | 1991-12-05 | 1996-02-29 | Alfatec Pharma Gmbh | Sol-gesteuerte Thermokolloidmatrix auf Gelatinebasis für perorale Retardformen |
| EP0911398B1 (en) | 1991-12-06 | 2008-06-11 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Phosphorylation epitopes of Tau protein for the diagnosis and treatment of Alzheimer's disease |
| JPH06289015A (ja) | 1993-03-30 | 1994-10-18 | Sunstar Inc | フェノチアジン系色源体安定化組成物 |
| GB9316727D0 (en) | 1993-08-12 | 1993-09-29 | Inst Of Psychiatry | Models of alzheimers's disease |
| GB9317193D0 (en) | 1993-08-18 | 1993-10-06 | Zeneca Ltd | Method |
| CA2196529A1 (en) | 1994-08-08 | 1996-02-22 | Peter Davies | Methods for treating and/or preventing alzheimer's disease using phenothiazines and/or thioxanthenes |
| DE4430091A1 (de) | 1994-08-25 | 1996-02-29 | Bayer Ag | Verwendung von N-substituierten Phenothiazinen |
| US5804601A (en) | 1995-04-10 | 1998-09-08 | Takeda Chemical Industries, Ltd. | Aromatic hydroxamic acid compounds, their production and use |
| US5693638A (en) * | 1996-02-23 | 1997-12-02 | Myers; Daniel | Method of treating a migraine headache |
| US6333322B1 (en) | 1996-03-13 | 2001-12-25 | Eisai Co., Ltd. | Nitrogen-containing tricyclic compounds and drugs containing the same |
| AU740547B2 (en) | 1997-01-21 | 2001-11-08 | American National Red Cross, The | Intracellular and extracellular decontamination of whole blood and blood components by amphiphilic phenothiazin-5-ium dyes plus light |
| WO1999062548A1 (en) | 1998-06-01 | 1999-12-09 | Advanced Research And Technology Institute | Methods and compositions for diagnosing tauopathies |
| FR2788436A1 (fr) | 1999-01-14 | 2000-07-21 | Pf Medicament | Composition d'un derive de phenothiazine |
| AU2001229619A1 (en) | 2000-01-21 | 2001-07-31 | Pharmacia And Upjohn Company | Transgenic mouse model of human neurodegenerative disease |
| GB0017060D0 (en) | 2000-07-11 | 2000-08-30 | Hunter Fleming Ltd | Production, stabilisation and use of reduced forms of pharmaceutical compounds |
| GB0100119D0 (en) | 2001-01-03 | 2001-02-14 | Univ Aberdeen | Materials and methods relating to protein aggregation in neurodegenerative disease |
| GB0106953D0 (en) | 2001-03-20 | 2001-05-09 | Univ Aberdeen | Neufofibrillary labels |
| US20020197258A1 (en) | 2001-06-22 | 2002-12-26 | Ghanbari Hossein A. | Compositions and methods for preventing protein aggregation in neurodegenerative diseases |
| GB0117326D0 (en) | 2001-07-16 | 2001-09-05 | Univ Aberdeen | Napthoquinone-type inhibitors of protein aggregation |
| US7410965B2 (en) | 2002-05-29 | 2008-08-12 | Gruenenthal Gmbh | Delayed release pharmaceutical composition containing 1-dimethyl-amino-3-(3-methoxyphenyl)-2-methyl-pentan-3-ol |
| US6953974B2 (en) * | 2003-08-26 | 2005-10-11 | Texas Instruments Incorporated | EEPROM device and method for providing lower programming voltage |
| GB0322756D0 (en) | 2003-09-29 | 2003-10-29 | Univ Aberdeen | Methods of chemical synthesis |
| JP2007512297A (ja) | 2003-11-28 | 2007-05-17 | フォトファーマイカ リミテッド | 生物活性メチレンブルー誘導体(2)における開発 |
| CN101084204B (zh) * | 2004-09-23 | 2012-12-05 | 卫思道制药有限公司 | 包括亚甲蓝(mtc)在内的二氨基吩噻嗪鎓化合物的化学合成和纯化方法 |
| EP2322517B1 (en) | 2004-09-23 | 2019-04-24 | WisTa Laboratories Ltd. | Methods of chemical synthesis and purification of diaminophenothiazinium compounds including methylthioninium chloride (mtc) |
| WO2007056439A1 (en) * | 2005-11-08 | 2007-05-18 | Collegium Pharmaceutical, Inc. | Salts of methylene blue and its derivatives |
| AU2007231126B2 (en) | 2006-03-29 | 2012-11-01 | TauRx Therapeutics Management Ltd | Inhibitors of protein aggregation |
| EP2853293B1 (en) | 2006-03-29 | 2017-11-22 | WisTa Laboratories Ltd. | Thioninium compounds and their use |
| DE602007008550D1 (de) | 2006-03-29 | 2010-09-30 | Wista Lab Ltd | 3,7-diamino-10h-phenothiazinsalze und ihre verwendung |
| US7956183B2 (en) | 2006-07-11 | 2011-06-07 | Wista Laboratories Ltd. | Methods of synthesis and/or purification of diaminophenothiazinium compounds |
| PL2167095T3 (pl) | 2007-06-19 | 2019-11-29 | Wista Lab Ltd | Związki fenotiazynowe do leczenia łagodnych zaburzeń poznawczych |
| MY161656A (en) | 2007-10-03 | 2017-04-28 | Wista Lab Ltd | Therapeutic use of diaminophenothiazines |
| RS55237B1 (sr) | 2011-02-11 | 2017-02-28 | Wis Ta Laboratories Ltd | Fenotiazin diaminijum soli i njihova primena |
| GB201614834D0 (en) | 2016-09-01 | 2016-10-19 | Wista Lab Ltd | Treatment of dementia |
| JP7317787B2 (ja) | 2020-10-19 | 2023-07-31 | トヨタ自動車株式会社 | 排ガス浄化装置 |
-
2007
- 2007-03-28 DE DE602007008550T patent/DE602007008550D1/de active Active
- 2007-03-28 KR KR1020087026537A patent/KR100983301B1/ko active Active
- 2007-03-28 HR HRP20100614TT patent/HRP20100614T4/hr unknown
- 2007-03-28 AT AT07732164T patent/ATE478058T3/de unknown
- 2007-03-28 CN CN201510002371.8A patent/CN104529939B/zh active Active
- 2007-03-28 PL PL07732164T patent/PL2013191T6/pl unknown
- 2007-03-28 ES ES07732164T patent/ES2349322T7/es active Active
- 2007-03-28 PT PT07732164T patent/PT2013191E/pt unknown
- 2007-03-28 WO PCT/GB2007/001103 patent/WO2007110627A2/en not_active Ceased
- 2007-03-28 CN CN201410269784.8A patent/CN104119294B/zh active Active
- 2007-03-28 EA EA200870384A patent/EA014552B1/ru unknown
- 2007-03-28 US US12/294,599 patent/US7888350B2/en active Active
- 2007-03-28 DK DK07732164.4T patent/DK2013191T6/en active
- 2007-03-28 CN CN200780020349.XA patent/CN101460472B/zh active Active
- 2007-03-28 CA CA2646163A patent/CA2646163C/en active Active
- 2007-03-28 JP JP2009502205A patent/JP5520043B2/ja active Active
- 2007-03-28 CN CN201510002365.2A patent/CN104606199B/zh active Active
- 2007-03-28 MY MYPI20083821A patent/MY143757A/en unknown
- 2007-03-28 EP EP07732164.4A patent/EP2013191B3/en active Active
- 2007-03-28 AU AU2007231124A patent/AU2007231124B2/en active Active
- 2007-03-28 CN CN201811196758.1A patent/CN109384741B/zh active Active
-
2008
- 2008-10-02 IL IL194516A patent/IL194516A/en active IP Right Grant
-
2013
- 2013-02-14 JP JP2013026635A patent/JP5814957B2/ja active Active
- 2013-11-14 JP JP2013236080A patent/JP2014055165A/ja active Pending
-
2014
- 2014-04-03 IL IL231890A patent/IL231890A/en active IP Right Grant
-
2015
- 2015-10-30 US US14/929,111 patent/US11344558B2/en active Active
-
2022
- 2022-02-02 US US17/591,306 patent/US11951110B2/en active Active
-
2024
- 2024-03-05 US US18/595,985 patent/US12324810B2/en active Active
-
2025
- 2025-05-02 US US19/197,925 patent/US20250325557A1/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5220009A (en) * | 1990-05-03 | 1993-06-15 | Yeda Research And Development Company Limited | Phenothiazinium salts and their use for disinfecting aqueous effluents |
| WO1996030766A1 (en) * | 1995-03-27 | 1996-10-03 | F. Hoffmann-La Roche Ag | Inhibition of tau-tau-association |
| WO2002055720A2 (en) * | 2001-01-15 | 2002-07-18 | Univ Aberdeen | Materials and methods relating to protein aggregation in neurodegenerative disease |
Non-Patent Citations (1)
| Title |
|---|
| ZHANG XIAN ET AL.: "METHYLENE BLUE PREVENTS NEURODEGENERATION CAUSED BY ROTENONE IN THE RETINA". NEUROTOXICITY RESEARCH, HARWOOD ACADEMIC PUBLISHERS, LAUSANNE, CH, vol. 9, no, 1, 2006, pages 47-57, KHR008079753, ISSN: 1029-8428, examples * |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EA014552B1 (ru) | 3,7-диамино-10н-фенотиазиновые соли и их применение | |
| US9174954B2 (en) | 3,7-diamino-10H-phenothiazine salts and their use | |
| CN101511803B (zh) | 二氨基吩噻嗪*化合物的合成和/或纯化方法 | |
| JP5592261B2 (ja) | ジアミノフェノチアジンの治療的使用 | |
| CN101460222B (zh) | 锍化合物及其用途 | |
| KR102194167B1 (ko) | 타우병증의 치료를 위한 의약으로서 3,6-이중치환된 크산틸륨 염 | |
| HK1261726B (en) | 3,7-diamino-10h-phenothiazine salts and their use | |
| HK1210047B (en) | 3,7-diamino-10h-phenothiazine salts and their use | |
| HK1261726A1 (en) | 3,7-diamino-10h-phenothiazine salts and their use | |
| HK1126480B (en) | 3, 7-diamino-10h-phenothiazine salts and their use | |
| HK1209417B (zh) | 3,7-二氨基-10h-吩噻嗪化合物盐及其用途 | |
| HK1199444B (zh) | 3,7-二氨基-10h-吩噻嗪化合物的制备方法 |