JP2010538023A5 - - Google Patents
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- Publication number
- JP2010538023A5 JP2010538023A5 JP2010523259A JP2010523259A JP2010538023A5 JP 2010538023 A5 JP2010538023 A5 JP 2010538023A5 JP 2010523259 A JP2010523259 A JP 2010523259A JP 2010523259 A JP2010523259 A JP 2010523259A JP 2010538023 A5 JP2010538023 A5 JP 2010538023A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- alkyl
- dithiolopyrrolone
- pharmaceutically acceptable
- 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.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 16
- -1 dithiolopyrrolone compound Chemical class 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 4
- 125000006618 5- to 10-membered aromatic heterocyclic group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
- KDDABMWLWNRHGO-UHFFFAOYSA-N dithiolo[4,3-b]pyrrole 1-oxide Chemical class N1=CC=C2S(=O)SC=C21 KDDABMWLWNRHGO-UHFFFAOYSA-N 0.000 claims 5
- 150000007530 organic bases Chemical class 0.000 claims 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 210000000265 leukocyte Anatomy 0.000 claims 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 239000000010 aprotic solvent Substances 0.000 claims 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- 239000003513 alkali Substances 0.000 claims 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 210000000440 neutrophil Anatomy 0.000 claims 2
- 230000002093 peripheral effect Effects 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- FJDAWPHHQRPQHM-UHFFFAOYSA-N C=CS(NC(CC1)CN1S(C(C1=C2)=C(C(N)=O)NC1=CC=C2Br)(=O)=O)(=O)=O Chemical compound C=CS(NC(CC1)CN1S(C(C1=C2)=C(C(N)=O)NC1=CC=C2Br)(=O)=O)(=O)=O FJDAWPHHQRPQHM-UHFFFAOYSA-N 0.000 claims 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims 1
- LFAWYQWJAQRLPJ-UHFFFAOYSA-N [Cl].NC=O Chemical compound [Cl].NC=O LFAWYQWJAQRLPJ-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims 1
- 239000000920 calcium hydroxide Substances 0.000 claims 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims 1
- 238000002512 chemotherapy Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000011736 potassium bicarbonate Substances 0.000 claims 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims 1
- 235000015497 potassium bicarbonate Nutrition 0.000 claims 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 claims 1
- 238000001959 radiotherapy Methods 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 238000004809 thin layer chromatography Methods 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- 0 C*C(N(*)C1=C2SSC=C2N(*)C1=O)=O Chemical compound C*C(N(*)C1=C2SSC=C2N(*)C1=O)=O 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200710045600.X | 2007-09-05 | ||
| CN200710045600XA CN101381371B (zh) | 2007-09-05 | 2007-09-05 | 二硫杂环戊烯并吡咯酮类化合物及其制备方法和应用 |
| PCT/CN2008/072207 WO2009033396A1 (fr) | 2007-09-05 | 2008-08-29 | Composés dithiolopyrrolones, leur préparation et leur utilisation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010538023A JP2010538023A (ja) | 2010-12-09 |
| JP2010538023A5 true JP2010538023A5 (OSRAM) | 2013-01-24 |
| JP5186566B2 JP5186566B2 (ja) | 2013-04-17 |
Family
ID=40451580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010523259A Expired - Fee Related JP5186566B2 (ja) | 2007-09-05 | 2008-08-29 | ジチオロピロロン化合物類、それらの調製及び使用 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8258176B2 (OSRAM) |
| EP (1) | EP2192122B1 (OSRAM) |
| JP (1) | JP5186566B2 (OSRAM) |
| CN (1) | CN101381371B (OSRAM) |
| WO (1) | WO2009033396A1 (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102219724B (zh) * | 2010-05-17 | 2014-10-01 | 上海现代制药股份有限公司 | 吡咯酮类化合物及其制备方法和应用 |
| CN106310264B (zh) * | 2015-06-29 | 2019-05-10 | 上海医药工业研究院 | 包含二硫杂环戊烯并吡咯酮衍生物的组合物 |
| CN109535174B (zh) * | 2018-12-20 | 2020-06-12 | 桂林医学院 | 一种n-芳基二硫吡咯酮-吡喃酮杂合衍生物及其制备方法和应用 |
| CN110981888B (zh) * | 2019-11-28 | 2020-07-28 | 桂林医学院 | N-芳基二硫吡咯酮脲类和氨基酯类衍生物及其制备和应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2170498A (en) | 1985-02-04 | 1986-08-06 | Ici Plc | Processes for making fungicidal dithiolopyrrolones |
| JPS63284181A (ja) | 1987-05-14 | 1988-11-21 | Nippon Kayaku Co Ltd | ジチオロピロ−ル系化合物およびそれを有効成分とする農園芸用殺菌剤 |
| US6020360A (en) * | 1996-09-18 | 2000-02-01 | Webster; John M. | Anticancer property of dithiolopyrrolones |
| CA2212237A1 (en) * | 1997-09-05 | 1999-03-05 | John M. Webster | Novel antineoplastic agents |
| JPH11279179A (ja) | 1998-03-25 | 1999-10-12 | Nippon Kayaku Co Ltd | ジチオロピロール系化合物およびこれを有効成分とする農園芸用病害虫防除剤 |
| CA2421760A1 (en) | 2000-09-08 | 2002-03-14 | Massachusetts Institute Of Technology | G-csf analog compositions and methods |
| CN100347176C (zh) * | 2002-03-26 | 2007-11-07 | 天济药业（深圳）有限公司 | 具有治疗作用的新型二硫杂环戊烯并吡咯酮类化合物 |
| KR101377358B1 (ko) * | 2006-09-29 | 2014-03-27 | 웰리켐 바이오 테크 인크. | 디티올로피롤론 화합물 및 그의 치료 적용 |
-
2007
- 2007-09-05 CN CN200710045600XA patent/CN101381371B/zh not_active Expired - Fee Related
-
2008
- 2008-08-29 EP EP08800719.0A patent/EP2192122B1/en active Active
- 2008-08-29 WO PCT/CN2008/072207 patent/WO2009033396A1/zh not_active Ceased
- 2008-08-29 US US12/676,470 patent/US8258176B2/en not_active Expired - Fee Related
- 2008-08-29 JP JP2010523259A patent/JP5186566B2/ja not_active Expired - Fee Related
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