SK8495A3 - Chiral 1-imidazoletanol derivatives, method of their production and intermediates on their production - Google Patents
Chiral 1-imidazoletanol derivatives, method of their production and intermediates on their production Download PDFInfo
- Publication number
- SK8495A3 SK8495A3 SK84-95A SK8495A SK8495A3 SK 8495 A3 SK8495 A3 SK 8495A3 SK 8495 A SK8495 A SK 8495A SK 8495 A3 SK8495 A3 SK 8495A3
- Authority
- SK
- Slovakia
- Prior art keywords
- chiral
- formula
- nitro
- imidazole
- hydroxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- 239000000543 intermediate Substances 0.000 title abstract description 9
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
- -1 hydroxy, methyl Chemical group 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 9
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- AMSDWLOANMAILF-UHFFFAOYSA-N 2-imidazol-1-ylethanol Chemical class OCCN1C=CN=C1 AMSDWLOANMAILF-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- LBKJNHPKYFYCLL-UHFFFAOYSA-N potassium;trimethyl(oxido)silane Chemical compound [K+].C[Si](C)(C)[O-] LBKJNHPKYFYCLL-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- SYFMSLVOHQZYEB-YFKPBYRVSA-N 2-nitro-1-[[(2s)-oxiran-2-yl]methyl]imidazole Chemical compound [O-][N+](=O)C1=NC=CN1C[C@@H]1OC1 SYFMSLVOHQZYEB-YFKPBYRVSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- ATZLNNCRLCUSCS-UHFFFAOYSA-N 3-[2-hydroxy-3-(2-nitroimidazol-1-yl)propyl]-1,3-oxazolidin-2-one Chemical compound C1=CN=C([N+]([O-])=O)N1CC(O)CN1CCOC1=O ATZLNNCRLCUSCS-UHFFFAOYSA-N 0.000 claims description 3
- SYFMSLVOHQZYEB-UHFFFAOYSA-N 2-nitro-1-(oxiran-2-ylmethyl)imidazole Chemical compound [O-][N+](=O)C1=NC=CN1CC1OC1 SYFMSLVOHQZYEB-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000003034 chemosensitisation Effects 0.000 abstract description 3
- 239000006114 chemosensitizer Substances 0.000 abstract description 2
- 125000005843 halogen group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- 239000000047 product Substances 0.000 description 38
- 239000000203 mixture Substances 0.000 description 31
- 239000007787 solid Substances 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
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- 241000699670 Mus sp. Species 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 6
- YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 description 5
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- 239000013078 crystal Substances 0.000 description 5
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 5
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- 238000012360 testing method Methods 0.000 description 5
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- 229940093915 gynecological organic acid Drugs 0.000 description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- SYFMSLVOHQZYEB-RXMQYKEDSA-N 2-nitro-1-[[(2r)-oxiran-2-yl]methyl]imidazole Chemical compound [O-][N+](=O)C1=NC=CN1C[C@H]1OC1 SYFMSLVOHQZYEB-RXMQYKEDSA-N 0.000 description 3
- LVXVRGPEXKQYPU-SNVBAGLBSA-N 3-[(2r)-3-(2-nitroimidazol-1-yl)-2-trimethylsilyloxypropyl]-1,3-oxazolidin-2-one Chemical compound C([C@H](O[Si](C)(C)C)CN1C(=NC=C1)[N+]([O-])=O)N1CCOC1=O LVXVRGPEXKQYPU-SNVBAGLBSA-N 0.000 description 3
- LVXVRGPEXKQYPU-JTQLQIEISA-N 3-[(2s)-3-(2-nitroimidazol-1-yl)-2-trimethylsilyloxypropyl]-1,3-oxazolidin-2-one Chemical compound C([C@@H](O[Si](C)(C)C)CN1C(=NC=C1)[N+]([O-])=O)N1CCOC1=O LVXVRGPEXKQYPU-JTQLQIEISA-N 0.000 description 3
- AUKCYOUETBBMFV-UHFFFAOYSA-N 3-trimethylsilyl-1,3-oxazolidin-2-one Chemical group C[Si](C)(C)N1CCOC1=O AUKCYOUETBBMFV-UHFFFAOYSA-N 0.000 description 3
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
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- 241001465754 Metazoa Species 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
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- 238000009835 boiling Methods 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
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- 201000011510 cancer Diseases 0.000 description 2
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- 229910052731 fluorine Inorganic materials 0.000 description 2
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- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 230000000637 radiosensitizating effect Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- AANLIOPOVSJZLY-RXMQYKEDSA-N (2s)-1-chloro-3-(2-nitroimidazol-1-yl)propan-2-ol Chemical compound ClC[C@@H](O)CN1C=CN=C1[N+]([O-])=O AANLIOPOVSJZLY-RXMQYKEDSA-N 0.000 description 1
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- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
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- ATZLNNCRLCUSCS-SSDOTTSWSA-N 3-[(2r)-2-hydroxy-3-(2-nitroimidazol-1-yl)propyl]-1,3-oxazolidin-2-one Chemical compound C([C@H](O)CN1C(=NC=C1)[N+]([O-])=O)N1CCOC1=O ATZLNNCRLCUSCS-SSDOTTSWSA-N 0.000 description 1
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
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- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/91—Nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US92320992A | 1992-07-31 | 1992-07-31 | |
| PCT/US1993/006973 WO1994015922A1 (en) | 1992-07-31 | 1993-07-26 | Novel process for preparing chiral [[(2-bromoethyl)amino]methyl]-2-nitro-1h-imidazol-1-ethanol and related compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK8495A3 true SK8495A3 (en) | 1995-08-09 |
Family
ID=25448313
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK84-95A SK8495A3 (en) | 1992-07-31 | 1993-07-26 | Chiral 1-imidazoletanol derivatives, method of their production and intermediates on their production |
Country Status (12)
| Country | Link |
|---|---|
| US (4) | US5342959A (cs) |
| EP (1) | EP0652870A1 (cs) |
| JP (1) | JPH07509489A (cs) |
| KR (1) | KR950702537A (cs) |
| AU (1) | AU4784293A (cs) |
| CA (1) | CA2136328A1 (cs) |
| CZ (1) | CZ10395A3 (cs) |
| FI (1) | FI950383A7 (cs) |
| HU (1) | HUT71347A (cs) |
| MX (1) | MX9304399A (cs) |
| SK (1) | SK8495A3 (cs) |
| WO (1) | WO1994015922A1 (cs) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX9304399A (es) * | 1992-07-31 | 1994-02-28 | Warner Lambert Co | Proceso novedoso para preparar [[2-bromoetil)-amino]metil]-2-nitro-1h-imidazol-1-etanol quiral y compuestos relacionados. |
| US6060604A (en) * | 1995-03-31 | 2000-05-09 | Florida State University | Pharmaceutical compounds comprising polyamines substituted with electron-affinic groups |
| US5965621A (en) * | 1995-08-17 | 1999-10-12 | Allergan | Methods and compositions for reducing or maintaining body weight in a mammal |
| US6331286B1 (en) | 1998-12-21 | 2001-12-18 | Photogen, Inc. | Methods for high energy phototherapeutics |
| US8974363B2 (en) * | 1997-12-11 | 2015-03-10 | Provectus Pharmatech, Inc. | Topical medicaments and methods for photodynamic treatment of disease |
| US20090117199A1 (en) * | 1998-08-06 | 2009-05-07 | Scott Timothy C | Method of treatment of cancer |
| US8557298B2 (en) * | 1998-08-06 | 2013-10-15 | Provectus Pharmatech, Inc. | Medicaments for chemotherapeutic treatment of disease |
| US20020001567A1 (en) * | 1998-12-21 | 2002-01-03 | Photogen, Inc. | Intracorporeal medicaments for high energy phototherapeutic treatment of disease |
| US8470296B2 (en) * | 1998-12-21 | 2013-06-25 | Provectus Pharmatech, Inc. | Intracorporeal medicaments for high energy phototherapeutic treatment of disease |
| US7384623B1 (en) | 1998-12-21 | 2008-06-10 | Provectus Pharmatech, Inc. | High energy phototherapeutic agents |
| AU2003300076C1 (en) | 2002-12-30 | 2010-03-04 | Angiotech International Ag | Drug delivery from rapid gelling polymer composition |
| EP1590440A4 (en) * | 2003-02-03 | 2009-03-18 | Palo Alto Inst Of Molecular Me | CELL-KILLING MOLECULES AND METHODS FOR THEIR USE |
| CN1314396C (zh) * | 2005-04-28 | 2007-05-09 | 南京圣和药业有限公司 | 左旋奥硝唑在制备抗厌氧菌感染药物的应用 |
| CN1332662C (zh) * | 2005-04-29 | 2007-08-22 | 南京圣和药业有限公司 | 左旋奥硝唑的静脉给药制剂及其制备方法 |
| CN1305469C (zh) * | 2005-07-08 | 2007-03-21 | 南京圣和药业有限公司 | 左旋奥硝唑在制备抗寄生虫感染的药物中的应用 |
| US7875602B2 (en) * | 2005-10-21 | 2011-01-25 | Sutter West Bay Hospitals | Camptothecin derivatives as chemoradiosensitizing agents |
| CN100368402C (zh) * | 2005-11-16 | 2008-02-13 | 沈阳中海生物技术开发有限公司 | 奥硝唑光学对映体的制备方法 |
| CN112774569B (zh) * | 2021-01-11 | 2022-04-08 | 江门市华熊新材料有限公司 | 含氟咪唑表面活性剂及其制备方法与应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE47132B1 (en) * | 1977-08-19 | 1983-12-28 | Roche Products Ltd | Novel nitroimidazoles and pharmaceutical preparations containing these as well as their manufacture |
| US4282232A (en) * | 1979-04-26 | 1981-08-04 | Research Corporation | Nitroimidazole radiosensitizers for hypoxic tumor cells and compositions thereof |
| ATE23041T1 (de) * | 1982-05-27 | 1986-11-15 | Nat Res Dev | Verbindungen anwendbar in strahlentherapie und chemotherapie. |
| US4946496A (en) * | 1982-06-01 | 1990-08-07 | E. I. Du Pont De Nemours And Company | Herbicidal diazoles |
| US5098921A (en) * | 1987-12-04 | 1992-03-24 | National Research Development Corporation | Nitro-substituted aromatic or hetero-aromatic compounds for use in cancer treatment |
| US4954515A (en) * | 1988-11-25 | 1990-09-04 | Warner-Lambert Company | Haloalkylaminomethyl-2-nitro-1H-imidazoles |
| MX9304399A (es) * | 1992-07-31 | 1994-02-28 | Warner Lambert Co | Proceso novedoso para preparar [[2-bromoetil)-amino]metil]-2-nitro-1h-imidazol-1-etanol quiral y compuestos relacionados. |
-
1993
- 1993-07-21 MX MX9304399A patent/MX9304399A/es unknown
- 1993-07-26 CZ CZ95103A patent/CZ10395A3/cs unknown
- 1993-07-26 SK SK84-95A patent/SK8495A3/sk unknown
- 1993-07-26 EP EP93918364A patent/EP0652870A1/en not_active Withdrawn
- 1993-07-26 WO PCT/US1993/006973 patent/WO1994015922A1/en not_active Ceased
- 1993-07-26 HU HU9500269A patent/HUT71347A/hu unknown
- 1993-07-26 JP JP6512556A patent/JPH07509489A/ja active Pending
- 1993-07-26 KR KR1019950700361A patent/KR950702537A/ko not_active Withdrawn
- 1993-07-26 CA CA002136328A patent/CA2136328A1/en not_active Abandoned
- 1993-07-26 AU AU47842/93A patent/AU4784293A/en not_active Abandoned
- 1993-08-05 US US08/102,658 patent/US5342959A/en not_active Expired - Fee Related
-
1994
- 1994-12-19 US US08/359,226 patent/US5481000A/en not_active Expired - Fee Related
-
1995
- 1995-01-27 FI FI950383A patent/FI950383A7/fi not_active Application Discontinuation
- 1995-05-18 US US08/443,548 patent/US5543527A/en not_active Expired - Fee Related
- 1995-05-23 US US08/447,463 patent/US5659048A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CZ10395A3 (en) | 1995-11-15 |
| US5659048A (en) | 1997-08-19 |
| JPH07509489A (ja) | 1995-10-19 |
| EP0652870A1 (en) | 1995-05-17 |
| US5342959A (en) | 1994-08-30 |
| US5481000A (en) | 1996-01-02 |
| CA2136328A1 (en) | 1994-07-21 |
| HUT71347A (en) | 1995-11-28 |
| US5543527A (en) | 1996-08-06 |
| WO1994015922A1 (en) | 1994-07-21 |
| HU9500269D0 (en) | 1995-03-28 |
| MX9304399A (es) | 1994-02-28 |
| FI950383A0 (fi) | 1995-01-27 |
| KR950702537A (ko) | 1995-07-29 |
| FI950383A7 (fi) | 1995-01-27 |
| AU4784293A (en) | 1994-08-15 |
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