CN1605586A - Alpha-substituted 2-methyl-5-nitroimidazole-1-ethanol derivatives - Google Patents
Alpha-substituted 2-methyl-5-nitroimidazole-1-ethanol derivatives Download PDFInfo
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- CN1605586A CN1605586A CN 200310100057 CN200310100057A CN1605586A CN 1605586 A CN1605586 A CN 1605586A CN 200310100057 CN200310100057 CN 200310100057 CN 200310100057 A CN200310100057 A CN 200310100057A CN 1605586 A CN1605586 A CN 1605586A
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- -1 Alpha-substituted 2-methyl-5-nitroimidazole-1-ethanol Chemical class 0.000 title abstract description 13
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- GCFBRXLSHGKWDP-XCGNWRKASA-N cefoperazone Chemical compound O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC(O)=CC=1)C(=O)N[C@@H]1C(=O)N2C(C(O)=O)=C(CSC=3N(N=NN=3)C)CS[C@@H]21 GCFBRXLSHGKWDP-XCGNWRKASA-N 0.000 description 1
- 229960005495 cefotetan Drugs 0.000 description 1
- SRZNHPXWXCNNDU-RHBCBLIFSA-N cefotetan Chemical compound N([C@]1(OC)C(N2C(=C(CSC=3N(N=NN=3)C)CS[C@@H]21)C(O)=O)=O)C(=O)C1SC(=C(C(N)=O)C(O)=O)S1 SRZNHPXWXCNNDU-RHBCBLIFSA-N 0.000 description 1
- 229960002682 cefoxitin Drugs 0.000 description 1
- 229960001991 ceftizoxime Drugs 0.000 description 1
- NNULBSISHYWZJU-LLKWHZGFSA-N ceftizoxime Chemical compound N([C@@H]1C(N2C(=CCS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 NNULBSISHYWZJU-LLKWHZGFSA-N 0.000 description 1
- 210000001175 cerebrospinal fluid Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- DHSUYTOATWAVLW-WFVMDLQDSA-N cilastatin Chemical compound CC1(C)C[C@@H]1C(=O)N\C(=C/CCCCSC[C@H](N)C(O)=O)C(O)=O DHSUYTOATWAVLW-WFVMDLQDSA-N 0.000 description 1
- 229960004912 cilastatin Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229960003324 clavulanic acid Drugs 0.000 description 1
- HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 description 1
- 229960002227 clindamycin Drugs 0.000 description 1
- KDLRVYVGXIQJDK-AWPVFWJPSA-N clindamycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@H](C)Cl)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 KDLRVYVGXIQJDK-AWPVFWJPSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 238000009112 empiric therapy Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 125000005908 glyceryl ester group Chemical group 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229960001375 lactose Drugs 0.000 description 1
- DBTMGCOVALSLOR-VPNXCSTESA-N laminarin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1O[C@@H]1[C@@H](O)C(O[C@H]2[C@@H]([C@@H](CO)OC(O)[C@@H]2O)O)O[C@H](CO)[C@H]1O DBTMGCOVALSLOR-VPNXCSTESA-N 0.000 description 1
- 229960000433 latamoxef Drugs 0.000 description 1
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- 239000002609 medium Substances 0.000 description 1
- 210000002752 melanocyte Anatomy 0.000 description 1
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- 239000003094 microcapsule Substances 0.000 description 1
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- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 210000002200 mouth mucosa Anatomy 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 210000003928 nasal cavity Anatomy 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960002292 piperacillin Drugs 0.000 description 1
- 229940104641 piperacillin / tazobactam Drugs 0.000 description 1
- WCMIIGXFCMNQDS-IDYPWDAWSA-M piperacillin sodium Chemical compound [Na+].O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC=CC=1)C(=O)N[C@@H]1C(=O)N2[C@@H](C([O-])=O)C(C)(C)S[C@@H]21 WCMIIGXFCMNQDS-IDYPWDAWSA-M 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 229940093916 potassium phosphate Drugs 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
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- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 1
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
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- 239000007940 sugar coated tablet Substances 0.000 description 1
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- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229960004659 ticarcillin Drugs 0.000 description 1
- OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
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- 239000000080 wetting agent Substances 0.000 description 1
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Medicine | Fragile plan bacterium | Prey viable bacteria porphyrin bacterium | Fusobacterium | Peptostreptococcus | Clostridium | No brood cell G bacillus |
Amoxicillin/clavulanate | +++ | +++ | +++ | +++ | +++ | +++ |
Ampicillin Trihydrate/Sulbactam | +++ | +++ | +++ | +++ | +++ | +++ |
Ticarcillin/clavulanic acid | +++ | +++ | +++ | +++ | +++ | +++ |
Piperacillin/tazobactam | +++ | ++/+++ | +++ | +++ | +++ | +++ |
Cefoperazone/Sulbactam | +++ | +++ | +++ | +++ | + | ++ |
Imipenum/cilastatin | +++ | +++ | +++ | +++ | +++ | +++ |
Paraxin | +++ | +++ | +++ | +++ | +++ | +++ |
Metronidazole | +++ | +++ | +++ | +++ | +++ | -/++ |
Clindamycin | ++ | ++/+++ | +++ | +++ | ++ | ++/+++ |
Penicillin G | - | -/+ | +++ | +++ | +++ | +++ |
Piperacillin | ++ | ++/+++ | +++ | +++ | +++ | +++ |
Cefoxitin | ++ | ++/+++ | +++ | +++ | ++ | +++ |
Cefotetan | ++ | ++/+ | ++ | +++ | ++ | ++ |
Ceftizoxime | ++ | ++/+++ | +++ | +++ | + | ++/+++ |
Latamoxef | ++ | +/+++ | ++ | +++ | ++ | ++ |
Compound (embodiment number) | ??????????MIC(μg/ml) | |
Fragile like bacillus | Peptostreptococcus | |
12345678 Ornidazoles | ????2 ????2 ????2 ????2 ????2 ????1 ????1 ????2 ????2 | ????0.5 ????1 ????1 ????1 ????0.5 ????0.5 ????0.25 ????0.5 ????0.5 |
Compound (embodiment number) | Oral ED 50(mg/kg) | Intravenously administrable ED 50(mg/kg) | ||
Fragile like bacillus | Peptostreptococcus | Fragile like bacillus | Peptostreptococcus | |
12345678 Ornidazoles | ????7 ????18 ????29 ????49 ????40 ????48 ????29 ????10 ????42 | ????16 ????16 ????18 ????30 ????25 ????29 ????12 ????12 ????20 | ????3.6 ????10 ????21 ????20 ????15 ????20 ????21 ????7 ????30 | ????7 ????10 ????15 ????9 ????8 ????10 ????5 ????8 ????10 |
Compound (embodiment) | Oral 2000mg/kg mortality ratio | Abdominal injection 2000mg/kg mortality ratio |
12345678 Ornidazoles | ????0 ????0 ????0 ????0 ????1 ????3 ????0 ????0 ????5 | ????3 ????2 ????2 ????0 ????3 ????5 ????0 ????0 ????7 |
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2003101000570A CN100344626C (en) | 2003-10-08 | 2003-10-08 | Application of alpha- (morpholine-1-yl) methyl-2-methyl-5-nitroimidazole-1-ethanol in preparation of anti-anaerobe drugs |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2003101000570A CN100344626C (en) | 2003-10-08 | 2003-10-08 | Application of alpha- (morpholine-1-yl) methyl-2-methyl-5-nitroimidazole-1-ethanol in preparation of anti-anaerobe drugs |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1605586A true CN1605586A (en) | 2005-04-13 |
CN100344626C CN100344626C (en) | 2007-10-24 |
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ID=34755805
Family Applications (1)
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CNB2003101000570A Expired - Lifetime CN100344626C (en) | 2003-10-08 | 2003-10-08 | Application of alpha- (morpholine-1-yl) methyl-2-methyl-5-nitroimidazole-1-ethanol in preparation of anti-anaerobe drugs |
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CN (1) | CN100344626C (en) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007079653A1 (en) * | 2006-01-06 | 2007-07-19 | Jiangsu Hansen Pharmaceutical Co., Ltd. | OPTICALLY PURE α-SUBSTITUTED 2-METHYL-5-NITROIMIDAZOLE-1-ETHANOL DERIVATIVES |
CN100387233C (en) * | 2006-06-09 | 2008-05-14 | 南京圣和药业有限公司 | Use of levo morpholine nidazole for preparing medicine for antiparasitic infection |
CN100427094C (en) * | 2005-12-13 | 2008-10-22 | 江苏豪森药业股份有限公司 | Application of alpha- (morpholine-1-yl) methyl-2-methyl-5-nitroimidazole-1-ethanol in preparation of anti-trichomonad and anti-amebiasis medicines |
CN1810815B (en) * | 2006-03-08 | 2011-03-16 | 陕西合成药业有限公司 | Nitroimidazole derivative for treatment |
CN1903846B (en) * | 2006-08-15 | 2011-07-13 | 杨成 | Ornidazole derivative used for therapy, its preparation method and use |
CN102199147A (en) * | 2011-03-19 | 2011-09-28 | 陕西合成药业有限公司 | Nitroimidazole derivative in therapy |
CN104829541A (en) * | 2015-05-05 | 2015-08-12 | 江苏豪森药业股份有限公司 | High selectivity and high purity method for preparing morinidazole |
CN104844522A (en) * | 2015-05-05 | 2015-08-19 | 江苏豪森药业股份有限公司 | Morinidazole crystal and preparation method and medical application thereof |
CN107365272A (en) * | 2016-05-12 | 2017-11-21 | 陕西合成药业股份有限公司 | A kind of novel imidazole class compound and preparation method thereof and application medically |
CN114907250A (en) * | 2021-02-06 | 2022-08-16 | 华创合成制药股份有限公司 | Deuterated morpholine ornidazole and application thereof |
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2003
- 2003-10-08 CN CNB2003101000570A patent/CN100344626C/en not_active Expired - Lifetime
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
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CN100427094C (en) * | 2005-12-13 | 2008-10-22 | 江苏豪森药业股份有限公司 | Application of alpha- (morpholine-1-yl) methyl-2-methyl-5-nitroimidazole-1-ethanol in preparation of anti-trichomonad and anti-amebiasis medicines |
WO2007079653A1 (en) * | 2006-01-06 | 2007-07-19 | Jiangsu Hansen Pharmaceutical Co., Ltd. | OPTICALLY PURE α-SUBSTITUTED 2-METHYL-5-NITROIMIDAZOLE-1-ETHANOL DERIVATIVES |
CN1810815B (en) * | 2006-03-08 | 2011-03-16 | 陕西合成药业有限公司 | Nitroimidazole derivative for treatment |
CN100387233C (en) * | 2006-06-09 | 2008-05-14 | 南京圣和药业有限公司 | Use of levo morpholine nidazole for preparing medicine for antiparasitic infection |
CN1903846B (en) * | 2006-08-15 | 2011-07-13 | 杨成 | Ornidazole derivative used for therapy, its preparation method and use |
CN102199147A (en) * | 2011-03-19 | 2011-09-28 | 陕西合成药业有限公司 | Nitroimidazole derivative in therapy |
CN104829541A (en) * | 2015-05-05 | 2015-08-12 | 江苏豪森药业股份有限公司 | High selectivity and high purity method for preparing morinidazole |
CN104844522A (en) * | 2015-05-05 | 2015-08-19 | 江苏豪森药业股份有限公司 | Morinidazole crystal and preparation method and medical application thereof |
CN104844522B (en) * | 2015-05-05 | 2017-07-25 | 江苏豪森药业集团有限公司 | Morpholine nitre azoles crystal and preparation method thereof and medical usage |
CN107365272A (en) * | 2016-05-12 | 2017-11-21 | 陕西合成药业股份有限公司 | A kind of novel imidazole class compound and preparation method thereof and application medically |
CN114907250A (en) * | 2021-02-06 | 2022-08-16 | 华创合成制药股份有限公司 | Deuterated morpholine ornidazole and application thereof |
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