NZ336606A - Terbenzimidazoles useful for treating fungal infection and cancer (topoisomerase inhibitors) - Google Patents
Terbenzimidazoles useful for treating fungal infection and cancer (topoisomerase inhibitors)Info
- Publication number
- NZ336606A NZ336606A NZ336606A NZ33660698A NZ336606A NZ 336606 A NZ336606 A NZ 336606A NZ 336606 A NZ336606 A NZ 336606A NZ 33660698 A NZ33660698 A NZ 33660698A NZ 336606 A NZ336606 A NZ 336606A
- Authority
- NZ
- New Zealand
- Prior art keywords
- alkyl
- compound
- halogen
- halo
- topoisomerase
- Prior art date
Links
- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 26
- 201000011510 cancer Diseases 0.000 title claims abstract description 24
- 208000031888 Mycoses Diseases 0.000 title claims abstract description 16
- 206010017533 Fungal infection Diseases 0.000 title claims abstract description 15
- 239000003534 dna topoisomerase inhibitor Substances 0.000 title description 2
- 229940044693 topoisomerase inhibitor Drugs 0.000 title description 2
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
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- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 abstract description 25
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229940016590 sarkosyl Drugs 0.000 description 1
- 108700004121 sarkosyl Proteins 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000003007 single stranded DNA break Effects 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 206010040882 skin lesion Diseases 0.000 description 1
- 231100000444 skin lesion Toxicity 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000007892 solid unit dosage form Substances 0.000 description 1
- 210000001082 somatic cell Anatomy 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000012089 stop solution Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 229960001278 teniposide Drugs 0.000 description 1
- BWMISRWJRUSYEX-SZKNIZGXSA-N terbinafine hydrochloride Chemical compound Cl.C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 BWMISRWJRUSYEX-SZKNIZGXSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 201000005060 thrombophlebitis Diseases 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 101150051314 tin-10 gene Proteins 0.000 description 1
- 201000003875 tinea corporis Diseases 0.000 description 1
- 201000004647 tinea pedis Diseases 0.000 description 1
- 201000005882 tinea unguium Diseases 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- GYUURHMITDQTRU-UHFFFAOYSA-N tributyl(pyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=N1 GYUURHMITDQTRU-UHFFFAOYSA-N 0.000 description 1
- UNEPXPMBVGDXGH-UHFFFAOYSA-N tributyl(pyridin-4-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=NC=C1 UNEPXPMBVGDXGH-UHFFFAOYSA-N 0.000 description 1
- GZJNLVYEAQGOSJ-UHFFFAOYSA-N tributyl-(4-chlorophenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=C(Cl)C=C1 GZJNLVYEAQGOSJ-UHFFFAOYSA-N 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical class CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- JLEXUIVKURIPFI-UHFFFAOYSA-N tris phosphate Chemical compound OP(O)(O)=O.OCC(N)(CO)CO JLEXUIVKURIPFI-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- A61P31/10—Antimycotics
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/786,629 US5770617A (en) | 1996-03-20 | 1997-01-21 | Terbenzimidazoles useful as antifungal agents |
| PCT/US1998/001005 WO1998031673A1 (en) | 1997-01-21 | 1998-01-21 | Terbenzimidazoles useful for medical therapy (topoisomerase inhibitors) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ336606A true NZ336606A (en) | 2001-04-27 |
Family
ID=25139154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ336606A NZ336606A (en) | 1997-01-21 | 1998-01-21 | Terbenzimidazoles useful for treating fungal infection and cancer (topoisomerase inhibitors) |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5770617A (OSRAM) |
| EP (1) | EP0960103A1 (OSRAM) |
| JP (1) | JP2002513399A (OSRAM) |
| KR (1) | KR20000070359A (OSRAM) |
| AU (1) | AU746663B2 (OSRAM) |
| CA (1) | CA2278452A1 (OSRAM) |
| IL (1) | IL130572A0 (OSRAM) |
| NZ (1) | NZ336606A (OSRAM) |
| PL (1) | PL334662A1 (OSRAM) |
| WO (1) | WO1998031673A1 (OSRAM) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1299358A (zh) * | 1997-12-31 | 2001-06-13 | 新泽西州州立大学(拉特格斯) | 杂环拓扑异构酶毒性剂 |
| IL137351A0 (en) | 1998-02-12 | 2001-07-24 | Univ Rutgers | Heterocyclic topoisomerase poisons |
| EP1191948A2 (en) * | 1999-06-11 | 2002-04-03 | Neorx Corporation | High dose radionuclide complexes for bone marrow suppression |
| US7094885B2 (en) * | 1999-07-11 | 2006-08-22 | Neorx Corporation | Skeletal-targeted radiation to treat bone-associated pathologies |
| US6740650B2 (en) | 1999-10-29 | 2004-05-25 | Rutgers, The State University Of New Jersey | Heterocyclic cytotoxic agents |
| AU2002249935A1 (en) * | 2001-01-08 | 2002-08-19 | Neorx Corporation | Radioactively labelled conjugates of phosphonates |
| MXPA04004607A (es) * | 2001-11-14 | 2004-09-10 | Univ Rutgers | Agentes de venenos de topoisomerasa solubilizados. |
| AU2002352708A1 (en) | 2001-11-14 | 2003-05-26 | Edmond J. Lavoie | Cytotoxic agents |
| KR20050044491A (ko) * | 2001-11-14 | 2005-05-12 | 루트거스, 더 스테이트 유니버시티 | 가용화된 토포이소머라제 독 |
| WO2003047505A2 (en) * | 2001-11-14 | 2003-06-12 | Rutgers, The State University | Topoisomerase poison agents |
| AU2002364552A1 (en) | 2001-12-13 | 2003-06-30 | Dow Global Technologies Inc. | Treatment of osteomyelitis with radiopharmaceuticals |
| US6992089B2 (en) * | 2002-08-09 | 2006-01-31 | Rutgers, The University Of New Jersey | Nitro and amino substituted topoisomerase agents |
| AU2003265405A1 (en) * | 2002-08-09 | 2004-02-25 | Edmond J. Lavoie | Nitro and amino substituted heterocycles as topoisomerase i targeting agents |
| WO2004014918A1 (en) * | 2002-08-09 | 2004-02-19 | Rutgers, The State University | Nitro and amino substituted topoisomerase agents |
| WO2004044174A2 (en) * | 2002-11-12 | 2004-05-27 | Rutgers, The State University | Topoisomerase-targeting agents |
| GB0619325D0 (en) | 2006-09-30 | 2006-11-08 | Univ Strathclyde | New compounds |
| GB0821913D0 (en) | 2008-12-02 | 2009-01-07 | Price & Co | Antibacterial compounds |
| EP2403856B1 (en) | 2009-03-06 | 2012-12-19 | Rutgers, The State University of New Jersey | Methylenedioxybenzo [i]phenanthridine derivatives used to treat cancer |
| WO2010127363A1 (en) | 2009-05-01 | 2010-11-04 | Rutgers, The State University Of New Jersey | Toposiomerase inhibitors |
| HRP20160397T1 (hr) * | 2010-06-01 | 2016-08-12 | Summit Therapeutics Plc | Spojevi za liječenje clostridium difficile povezanih bolesti |
| WO2015042438A1 (en) * | 2013-09-19 | 2015-03-26 | The Florida International Board Of Trustees Modesto A. Maidique Campus | Selective inhibition of bacterial topoisomerase i |
| GB201506658D0 (en) | 2015-04-20 | 2015-06-03 | Cellcentric Ltd | Pharmaceutical compounds |
| GB201506660D0 (en) | 2015-04-20 | 2015-06-03 | Cellcentric Ltd | Pharmaceutical compounds |
| WO2017125944A1 (en) * | 2016-01-23 | 2017-07-27 | Jawaharlal Nehru University (Jnu) | Broad spectrum antibacterial activity of novel bisbenzimidazoles targeting topoisomerase ia and the synergistic composition of bisbenzimidazole with efflux pump inhibitors against pathogenic bacteria |
| US11091498B2 (en) | 2016-04-04 | 2021-08-17 | Rutgers, The State University Of New Jersey | Topoisomerase poisons |
| WO2019004254A1 (ja) | 2017-06-27 | 2019-01-03 | 株式会社Ｋｙｕｌｕｘ | 発光材料、化合物、遅延蛍光体および発光素子 |
| JP7267563B2 (ja) | 2017-06-27 | 2023-05-02 | 株式会社Kyulux | 発光材料、化合物、遅延蛍光体および発光素子 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9608476A (pt) * | 1995-05-17 | 1999-08-17 | Univ Rutgers | Composto processo para inibir o crescimento de uma célula tumoral de mam¡fero e composicão terapéutica |
| US5643935A (en) * | 1995-06-07 | 1997-07-01 | The University Of North Carolina At Chapel Hill | Method of combatting infectious diseases using dicationic bis-benzimidazoles |
-
1997
- 1997-01-21 US US08/786,629 patent/US5770617A/en not_active Expired - Lifetime
-
1998
- 1998-01-21 AU AU61327/98A patent/AU746663B2/en not_active Ceased
- 1998-01-21 IL IL13057298A patent/IL130572A0/xx unknown
- 1998-01-21 PL PL98334662A patent/PL334662A1/xx unknown
- 1998-01-21 EP EP98905972A patent/EP0960103A1/en not_active Ceased
- 1998-01-21 WO PCT/US1998/001005 patent/WO1998031673A1/en not_active Ceased
- 1998-01-21 NZ NZ336606A patent/NZ336606A/en unknown
- 1998-01-21 JP JP53462498A patent/JP2002513399A/ja not_active Ceased
- 1998-01-21 CA CA002278452A patent/CA2278452A1/en not_active Abandoned
- 1998-01-21 KR KR1019997006592A patent/KR20000070359A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| AU6132798A (en) | 1998-08-07 |
| EP0960103A1 (en) | 1999-12-01 |
| JP2002513399A (ja) | 2002-05-08 |
| KR20000070359A (ko) | 2000-11-25 |
| AU746663B2 (en) | 2002-05-02 |
| US5770617A (en) | 1998-06-23 |
| IL130572A0 (en) | 2000-06-01 |
| CA2278452A1 (en) | 1998-07-23 |
| WO1998031673A1 (en) | 1998-07-23 |
| PL334662A1 (en) | 2000-03-13 |
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Legal Events
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| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) |