JP2012511560A5 - - Google Patents
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- JP2012511560A5 JP2012511560A5 JP2011540197A JP2011540197A JP2012511560A5 JP 2012511560 A5 JP2012511560 A5 JP 2012511560A5 JP 2011540197 A JP2011540197 A JP 2011540197A JP 2011540197 A JP2011540197 A JP 2011540197A JP 2012511560 A5 JP2012511560 A5 JP 2012511560A5
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- Japan
- Prior art keywords
- compound
- bis
- formula
- treatment
- saturated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000001875 compounds Chemical class 0.000 claims 91
- 238000011282 treatment Methods 0.000 claims 16
- 229920006395 saturated elastomer Polymers 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 238000000034 method Methods 0.000 claims 11
- 108010026424 tau Proteins Proteins 0.000 claims 11
- 102000013498 tau Proteins Human genes 0.000 claims 11
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 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 claims 8
- 230000007850 degeneration Effects 0.000 claims 6
- BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 208000024827 Alzheimer disease Diseases 0.000 claims 4
- 206010012289 Dementia Diseases 0.000 claims 4
- 201000010374 Down Syndrome Diseases 0.000 claims 4
- 201000002832 Lewy body dementia Diseases 0.000 claims 4
- 208000010577 Niemann-Pick disease type C Diseases 0.000 claims 4
- 208000027089 Parkinsonian disease Diseases 0.000 claims 4
- 206010034010 Parkinsonism Diseases 0.000 claims 4
- 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 claims 4
- 208000007930 Type C Niemann-Pick Disease Diseases 0.000 claims 4
- 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 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 229960004640 memantine Drugs 0.000 claims 4
- 208000036709 mucopolysaccharidosis type 3B Diseases 0.000 claims 4
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims 4
- NUMOZCKMSNMNGZ-UHFFFAOYSA-M xanthylium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C1=CC=CC2=CC3=CC=CC=C3[O+]=C21 NUMOZCKMSNMNGZ-UHFFFAOYSA-M 0.000 claims 4
- 229940126062 Compound A Drugs 0.000 claims 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 3
- 125000001931 aliphatic group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- -1 hexafluorophosphate Chemical compound 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- INCIMLINXXICKS-UHFFFAOYSA-M pyronin Y Chemical compound [Cl-].C1=CC(=[N+](C)C)C=C2OC3=CC(N(C)C)=CC=C3C=C21 INCIMLINXXICKS-UHFFFAOYSA-M 0.000 claims 3
- ZUTFXKDLQCQRKE-UHFFFAOYSA-N 2-n,2-n,8-n,8-n-tetramethylphenazin-5-ium-2,8-diamine;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C1=CC(N(C)C)=CC2=NC3=CC(N(C)C)=CC=C3[NH+]=C21 ZUTFXKDLQCQRKE-UHFFFAOYSA-N 0.000 claims 2
- BEQRSYYTAXIHOS-UHFFFAOYSA-N 2-n,2-n,8-n,8-n-tetramethylphenazine-2,8-diamine;hydrochloride Chemical compound Cl.C1=CC(N(C)C)=CC2=NC3=CC(N(C)C)=CC=C3N=C21 BEQRSYYTAXIHOS-UHFFFAOYSA-N 0.000 claims 2
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims 2
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims 2
- 101710137189 Amyloid-beta A4 protein Proteins 0.000 claims 2
- 101710151993 Amyloid-beta precursor protein Proteins 0.000 claims 2
- 102100022704 Amyloid-beta precursor protein Human genes 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- 229940122041 Cholinesterase inhibitor Drugs 0.000 claims 2
- NLJJQYLAORPFNI-UHFFFAOYSA-K Cl[Zn](Cl)Cl.C(C)N(C=1C=CC2=CC3=CC=C(C=C3[O+]=C2C1)N(CC)CC)CC Chemical compound Cl[Zn](Cl)Cl.C(C)N(C=1C=CC2=CC3=CC=C(C=C3[O+]=C2C1)N(CC)CC)CC NLJJQYLAORPFNI-UHFFFAOYSA-K 0.000 claims 2
- 101000891579 Homo sapiens Microtubule-associated protein tau Proteins 0.000 claims 2
- 208000009829 Lewy Body Disease Diseases 0.000 claims 2
- 102100040243 Microtubule-associated protein tau Human genes 0.000 claims 2
- 229940121743 Muscarinic receptor agonist Drugs 0.000 claims 2
- 206010068871 Myotonic dystrophy Diseases 0.000 claims 2
- ZJLIJGMBCGLMAN-UHFFFAOYSA-N N,N-dimethyl-2H-oxazin-2-ium-2-amine chloride Chemical compound [Cl-].CN(C)[NH+]1OC=CC=C1 ZJLIJGMBCGLMAN-UHFFFAOYSA-N 0.000 claims 2
- 229940099433 NMDA receptor antagonist Drugs 0.000 claims 2
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims 2
- 208000025820 Sanfilippo syndrome type B Diseases 0.000 claims 2
- 208000037065 Subacute sclerosing leukoencephalitis Diseases 0.000 claims 2
- 206010042297 Subacute sclerosing panencephalitis Diseases 0.000 claims 2
- 208000034799 Tauopathies Diseases 0.000 claims 2
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 2
- LCGAMMSHBVHDRY-UHFFFAOYSA-N [6-(dimethylamino)thioxanthen-3-ylidene]-dimethylazanium Chemical compound C1=CC(=[N+](C)C)C=C2SC3=CC(N(C)C)=CC=C3C=C21 LCGAMMSHBVHDRY-UHFFFAOYSA-N 0.000 claims 2
- SZBXPKZBJCWOGN-UHFFFAOYSA-M [6-(dimethylamino)thioxanthen-3-ylidene]-dimethylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C1=CC(=[N+](C)C)C=C2SC3=CC(N(C)C)=CC=C3C=C21 SZBXPKZBJCWOGN-UHFFFAOYSA-M 0.000 claims 2
- DZHSAHHDTRWUTF-SIQRNXPUSA-N amyloid-beta polypeptide 42 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(O)=O)[C@@H](C)CC)C(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C(C)C)C1=CC=CC=C1 DZHSAHHDTRWUTF-SIQRNXPUSA-N 0.000 claims 2
- 229940039856 aricept Drugs 0.000 claims 2
- 210000004227 basal ganglia Anatomy 0.000 claims 2
- 239000000544 cholinesterase inhibitor Substances 0.000 claims 2
- 210000000349 chromosome Anatomy 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 claims 2
- 208000017004 dementia pugilistica Diseases 0.000 claims 2
- 238000003745 diagnosis Methods 0.000 claims 2
- 229960003530 donepezil Drugs 0.000 claims 2
- 229940108366 exelon Drugs 0.000 claims 2
- 229960003980 galantamine Drugs 0.000 claims 2
- ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 claims 2
- CJFGBCWGOQRURQ-UHFFFAOYSA-N ginsenoside Mc Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OC(CO)C(O)C1O CJFGBCWGOQRURQ-UHFFFAOYSA-N 0.000 claims 2
- ZTQSADJAYQOCDD-UHFFFAOYSA-N ginsenoside-Rd2 Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O ZTQSADJAYQOCDD-UHFFFAOYSA-N 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 150000002500 ions Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 208000005340 mucopolysaccharidosis III Diseases 0.000 claims 2
- 208000011045 mucopolysaccharidosis type 3 Diseases 0.000 claims 2
- 208000012227 mucopolysaccharidosis type IIIB Diseases 0.000 claims 2
- 239000000472 muscarinic agonist Substances 0.000 claims 2
- 201000000585 muscular atrophy Diseases 0.000 claims 2
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 claims 2
- 229940033872 namenda Drugs 0.000 claims 2
- 230000009256 peri post natal development Effects 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 238000004393 prognosis Methods 0.000 claims 2
- 238000011321 prophylaxis Methods 0.000 claims 2
- 230000004845 protein aggregation Effects 0.000 claims 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims 2
- CXZRDVVUVDYSCQ-UHFFFAOYSA-M pyronin B Chemical compound [Cl-].C1=CC(=[N+](CC)CC)C=C2OC3=CC(N(CC)CC)=CC=C3C=C21 CXZRDVVUVDYSCQ-UHFFFAOYSA-M 0.000 claims 2
- BIOUTGSRJYRPFT-UHFFFAOYSA-N pyronin B(1+) Chemical compound C1=CC(=[N+](CC)CC)C=C2OC3=CC(N(CC)CC)=CC=C3C=C21 BIOUTGSRJYRPFT-UHFFFAOYSA-N 0.000 claims 2
- 229960004136 rivastigmine Drugs 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 230000009529 traumatic brain injury Effects 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- OIHZGFWAMWHYPA-UHFFFAOYSA-N xanthylium Chemical compound C1=CC=CC2=CC3=CC=CC=C3[O+]=C21 OIHZGFWAMWHYPA-UHFFFAOYSA-N 0.000 claims 2
- NQLPENYCOSFVSX-UHFFFAOYSA-N Cl.Cl.C1=C(N(CC)CC)C=C2OC3=CC(N(CC)CC)=CC=C3CC2=C1 Chemical compound Cl.Cl.C1=C(N(CC)CC)C=C2OC3=CC(N(CC)CC)=CC=C3CC2=C1 NQLPENYCOSFVSX-UHFFFAOYSA-N 0.000 claims 1
- 229910020366 ClO 4 Inorganic materials 0.000 claims 1
- PWRXRKRLQRNESS-UHFFFAOYSA-N [9-(2-carboxyethyl)-6-(dimethylamino)xanthen-3-ylidene]-dimethylazanium;chloride Chemical compound [Cl-].C1=CC(=[N+](C)C)C=C2OC3=CC(N(C)C)=CC=C3C(CCC(O)=O)=C21 PWRXRKRLQRNESS-UHFFFAOYSA-N 0.000 claims 1
- 230000002776 aggregation Effects 0.000 claims 1
- 238000004220 aggregation Methods 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 238000001514 detection method Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 238000002372 labelling Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 102000004169 proteins and genes Human genes 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 230000002441 reversible effect Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 0 CC**(*)C(*=CO*)=C[*@@](C)(*)*1C*CC1 Chemical compound CC**(*)C(*=CO*)=C[*@@](C)(*)*1C*CC1 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12128808P | 2008-12-10 | 2008-12-10 | |
| US61/121,288 | 2008-12-10 | ||
| PCT/GB2009/002865 WO2010067078A2 (en) | 2008-12-10 | 2009-12-10 | 3,6-disubstituted xanthylium salts as medicaments |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015042371A Division JP6148270B2 (ja) | 2008-12-10 | 2015-03-04 | ３，６−二置換キサンチリウム塩 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012511560A JP2012511560A (ja) | 2012-05-24 |
| JP2012511560A5 true JP2012511560A5 (enExample) | 2013-01-31 |
| JP5814125B2 JP5814125B2 (ja) | 2015-11-17 |
Family
ID=41716277
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011540197A Active JP5814125B2 (ja) | 2008-12-10 | 2009-12-10 | ３，６−二置換キサンチリウム塩 |
| JP2015042371A Active JP6148270B2 (ja) | 2008-12-10 | 2015-03-04 | ３，６−二置換キサンチリウム塩 |
| JP2016159662A Pending JP2017019823A (ja) | 2008-12-10 | 2016-08-16 | ３，６−二置換キサンチリウム塩 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015042371A Active JP6148270B2 (ja) | 2008-12-10 | 2015-03-04 | ３，６−二置換キサンチリウム塩 |
| JP2016159662A Pending JP2017019823A (ja) | 2008-12-10 | 2016-08-16 | ３，６−二置換キサンチリウム塩 |
Country Status (17)
| Country | Link |
|---|---|
| US (3) | US8658665B2 (enExample) |
| EP (4) | EP3112358B1 (enExample) |
| JP (3) | JP5814125B2 (enExample) |
| KR (6) | KR102358299B1 (enExample) |
| CN (2) | CN104367571A (enExample) |
| AU (1) | AU2009326173B2 (enExample) |
| BR (3) | BR122020004984B1 (enExample) |
| CA (3) | CA3176480A1 (enExample) |
| DK (3) | DK3689346T3 (enExample) |
| ES (3) | ES2799892T3 (enExample) |
| FI (1) | FI3689346T3 (enExample) |
| HK (1) | HK1207319A1 (enExample) |
| MX (3) | MX385354B (enExample) |
| PL (3) | PL3689346T3 (enExample) |
| PT (3) | PT2373660T (enExample) |
| SI (3) | SI3112358T1 (enExample) |
| WO (1) | WO2010067078A2 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2799892T3 (es) * | 2008-12-10 | 2020-12-22 | Wista Lab Ltd | Sales de xantilio 3,6-disustituidas |
| US8785434B2 (en) | 2010-04-30 | 2014-07-22 | Prosetta Antiviral Inc. | Antiviral compounds |
| US8828986B2 (en) | 2011-04-20 | 2014-09-09 | Prosetta Antiviral Inc. | Antiviral compounds |
| US20220288096A1 (en) * | 2013-05-07 | 2022-09-15 | Seelos Therapeutics, Inc. | Compositions and methods for treating an aggregation disease or disorder |
| US10493023B2 (en) | 2013-05-07 | 2019-12-03 | Seelos Therapeutics, Inc. | Treatment of protein aggregation myopathic and neurodegenerative diseases by parenteral administration of trehalose |
| WO2014196464A1 (ja) * | 2013-06-07 | 2014-12-11 | 株式会社Adeka | 着色感光性組成物及び新規化合物 |
| WO2016184911A1 (en) * | 2015-05-18 | 2016-11-24 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment of the neuropathology of patients suffering from myotonic dystrophy type 1 (dm1) |
| CN106009761B (zh) * | 2016-05-31 | 2017-08-15 | 延边大学 | 一种派洛宁染料的制备方法 |
| EP3357928B1 (en) | 2017-02-03 | 2021-01-06 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Novel dyes with phosphinic acid, phosphinate, phosphonate and phosphonamidate substituents as auxochromic groups and methods for preparing the same |
| CN108570032B (zh) * | 2017-03-09 | 2021-04-02 | 华东理工大学 | 新型罗丹明染料及其在抗致病菌中的应用 |
| WO2020019289A1 (zh) * | 2018-07-27 | 2020-01-30 | 华东理工大学 | 新型罗丹明染料及其在抗致病菌中的应用 |
| KR102496845B1 (ko) * | 2018-08-08 | 2023-02-08 | 서울대학교산학협력단 | 진단 지표로서 베타-아밀로이드 수준과 함께 혈장 타우 수준을 사용하는 알츠하이머병의 진단 및 치료 방법 |
| WO2021067243A1 (en) | 2019-10-01 | 2021-04-08 | Seelos Therapeutics, Inc. | Trehalose formulations and uses thereof |
| KR20220142451A (ko) * | 2020-01-24 | 2022-10-21 | 오레곤 헬스 앤드 사이언스 유니버시티 | 신경-특이적 영상화를 위한 옥사진-기재 형광단 화합물 |
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|---|---|---|---|---|
| DE65282C (de) | A. Leonhardt & Co. in Mühlheim i. H | Verfahren zur Ueberführung von Rhodaminfarbstoffen in gelbere Farbstoffe durch Oxydationsmittel | ||
| US2397423A (en) | 1943-03-17 | 1946-03-26 | Us Rubber Co | Parasiticidal preparations |
| US3284205A (en) * | 1963-09-17 | 1966-11-08 | Horizons Inc | Benzotriazole and heterocyclic ketimide activators for leuco compounds |
| US3620748A (en) | 1966-01-07 | 1971-11-16 | Horizons Research Inc | N-vinyl amine/halogen liberating composition sensitized with 9-vinyl carbazoles or polyacenes, or transannular peroxides of polyacenes |
| DE1915910A1 (de) * | 1969-03-28 | 1970-10-08 | Agfa Gevaert Ag | Spektral sensibilisierte photographische Direktpositiv-Emulsion |
| BE756085A (de) | 1969-09-12 | 1971-03-15 | Agfa Gevaert Nv | Spectraal gesensibiliseerd fotografisch materiaal |
| US3873940A (en) * | 1971-08-09 | 1975-03-25 | Eastman Kodak Co | Laser media containing rigidized dyes |
| US3932415A (en) * | 1972-04-17 | 1976-01-13 | Eastman Kodak Company | Pyrylium dyes having a fused rigidized nitrogen-containing ring |
| BE806408A (nl) | 1973-10-23 | 1974-04-23 | Oce Van Der Grinten Nv | Tonerpoeder voor het ontwikkelen van elektrostatische beelden |
| JPS52113738A (en) * | 1976-03-19 | 1977-09-24 | Canon Inc | Electrostatically developing toner |
| US4065315A (en) | 1976-04-26 | 1977-12-27 | Dynachem Corporation | Phototropic dye system and photosensitive compositions containing the same |
| CS193815B1 (en) | 1977-03-28 | 1979-11-30 | Jaroslav Senkyr | Fluid membranes in function of the ionto-convertors for the nitrate iont selective electrode |
| DE3322945A1 (de) * | 1983-06-25 | 1985-01-03 | Bayer Ag, 5090 Leverkusen | Laserfarbstoffe |
| JPS61165307A (ja) * | 1985-01-18 | 1986-07-26 | Asahi Chem Ind Co Ltd | ３，６−ジアミノキサンテン誘導体を含有する除草剤 |
| JPS62278571A (ja) | 1986-05-27 | 1987-12-03 | Ricoh Co Ltd | 静電荷像現像用トナ− |
| JPS63131148A (ja) | 1986-11-21 | 1988-06-03 | Ricoh Co Ltd | 静電潜像現像用乾式トナ− |
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