JP2008542376A5 - - Google Patents
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- Publication number
- JP2008542376A5 JP2008542376A5 JP2008514712A JP2008514712A JP2008542376A5 JP 2008542376 A5 JP2008542376 A5 JP 2008542376A5 JP 2008514712 A JP2008514712 A JP 2008514712A JP 2008514712 A JP2008514712 A JP 2008514712A JP 2008542376 A5 JP2008542376 A5 JP 2008542376A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- alkyl
- oxo
- thia
- azabicyclo
- 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.)
- Withdrawn
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- 229910052760 oxygen Inorganic materials 0.000 claims 76
- 229910052717 sulfur Inorganic materials 0.000 claims 58
- 229910052799 carbon Inorganic materials 0.000 claims 54
- 125000001072 heteroaryl group Chemical group 0.000 claims 42
- -1 substituted Chemical class 0.000 claims 36
- 159000000000 sodium salts Chemical class 0.000 claims 32
- 150000001721 carbon Chemical group 0.000 claims 30
- 125000005842 heteroatom Chemical group 0.000 claims 20
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 18
- 230000015572 biosynthetic process Effects 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 18
- 229920006395 saturated elastomer Polymers 0.000 claims 18
- 125000003003 spiro group Chemical group 0.000 claims 18
- FYZUENZXIZCLAZ-UHFFFAOYSA-N 2-methylhept-2-enoic acid Chemical compound CCCCC=C(C)C(O)=O FYZUENZXIZCLAZ-UHFFFAOYSA-N 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 125000003107 substituted aryl group Chemical group 0.000 claims 8
- 208000035143 Bacterial infection Diseases 0.000 claims 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims 6
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 6
- 208000022362 bacterial infectious disease Diseases 0.000 claims 6
- 239000003782 beta lactam antibiotic agent Substances 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 239000002132 β-lactam antibiotic Substances 0.000 claims 6
- 229940124586 β-lactam antibiotics Drugs 0.000 claims 6
- 239000000126 substance Substances 0.000 claims 5
- GRYKCKSOHDCZJF-YLBKJFSISA-N (5r,6z)-7-oxo-6-(4h-thieno[2,3]thiopyrano[2,4-b]pyridin-2-ylmethylidene)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C1SC2=NC=CC=C2C(S2)=C1C=C2/C=C1/C(=O)N2[C@@H]1SC=C2C(=O)O GRYKCKSOHDCZJF-YLBKJFSISA-N 0.000 claims 4
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 125000002619 bicyclic group Chemical group 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 238000001727 in vivo Methods 0.000 claims 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims 4
- OWKFKAWHZKUXBM-WSVPDTOYSA-N (5R,6Z)-6-[(7-methoxy-1,8,10-triazatricyclo[7.3.0.02,6]dodeca-2(6),7,9,11-tetraen-11-yl)methylidene]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound COC1=NC2=NC(\C=C/3C(N4C(=CS[C@@H]4\3)C(O)=O)=O)=CN2C2=C1CCC2 OWKFKAWHZKUXBM-WSVPDTOYSA-N 0.000 claims 2
- LVDAGEHCAGXUMS-VYLZPFMQSA-N (5R,6Z)-7-oxo-6-([1,3]thiazolo[3,2-a]benzimidazol-2-ylmethylidene)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound S1C2=NC3=CC=CC=C3N2C=C1/C=C1/C(=O)N2[C@@H]1SC=C2C(=O)O LVDAGEHCAGXUMS-VYLZPFMQSA-N 0.000 claims 2
- RITQDZWBRPLXHO-NUZRTGFDSA-N (5R,6Z)-7-oxo-6-[[7-(2-phenylmethoxyethoxy)-1,8,10-triazatricyclo[7.3.0.02,6]dodeca-2(6),7,9,11-tetraen-11-yl]methylidene]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound N1([C@@H]2SC=C1C(=O)O)C(=O)\C2=C\C(N=C1N=2)=CN1C=1CCCC=1C=2OCCOCC1=CC=CC=C1 RITQDZWBRPLXHO-NUZRTGFDSA-N 0.000 claims 2
- FNBVVWRNKCSCSF-JKLGPDONSA-N (5r,6e)-6-[(5-benzyl-6-oxobenzo[b][1,4]benzoxazepin-3-yl)methylidene]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound N1([C@@H]2SC=C1C(=O)O)C(=O)\C2=C/C(C=C12)=CC=C1OC1=CC=CC=C1C(=O)N2CC1=CC=CC=C1 FNBVVWRNKCSCSF-JKLGPDONSA-N 0.000 claims 2
- ZMVPSTWCZFOKMA-VYLZPFMQSA-N (5r,6z)-6-(1,2-dihydro-[1,3]thiazolo[3,2-a]benzimidazol-7-ylmethylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound N1([C@@H]2SC=C1C(=O)O)C(=O)\C2=C\C(C=C12)=CC=C1N=C1N2CCS1 ZMVPSTWCZFOKMA-VYLZPFMQSA-N 0.000 claims 2
- UIEWFJZVZVDQLA-IZIDJEDMSA-N (5r,6z)-6-(3,4-dihydro-2h-[1,3]thiazino[3,2-a]benzimidazol-7-ylmethylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound S1CCCN2C3=CC(/C=C4/C(=O)N5[C@@H]4SC=C5C(=O)O)=CC=C3N=C21 UIEWFJZVZVDQLA-IZIDJEDMSA-N 0.000 claims 2
- SBFSPMJWFBHKNG-UUKWBXHYSA-N (5r,6z)-6-(imidazo[1,2-a]quinolin-2-ylmethylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound N1=C2C=CC3=CC=CC=C3N2C=C1/C=C1/C(=O)N2[C@@H]1SC=C2C(=O)O SBFSPMJWFBHKNG-UUKWBXHYSA-N 0.000 claims 2
- SWNURUJCQSUVHE-MGDKSHQASA-N (5r,6z)-6-(imidazo[1,2-a]quinoxalin-2-ylmethylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound N1=C2C=NC3=CC=CC=C3N2C=C1/C=C1/C(=O)N2[C@@H]1SC=C2C(=O)O SWNURUJCQSUVHE-MGDKSHQASA-N 0.000 claims 2
- ZQZVENIYZGCSFN-VYLZPFMQSA-N (5r,6z)-6-(imidazo[2,1-b][1,3]benzothiazol-2-ylmethylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound N1=C2SC3=CC=CC=C3N2C=C1/C=C1/C(=O)N2[C@@H]1SC=C2C(=O)O ZQZVENIYZGCSFN-VYLZPFMQSA-N 0.000 claims 2
- VOFYPSOWJHHFAS-IZIDJEDMSA-N (5r,6z)-6-[(5-methyl-6,7,8,9-tetrahydro-[1,2,4]triazolo[1,5-a]quinazolin-2-yl)methylidene]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C1CCCC2=C1N1N=C(\C=C/3C(N4C(=CS[C@@H]4\3)C(O)=O)=O)N=C1N=C2C VOFYPSOWJHHFAS-IZIDJEDMSA-N 0.000 claims 2
- GVIJNDBUPIEBNV-VYLZPFMQSA-N (5r,6z)-6-[(5-methyl-7,8-dihydro-6h-cyclopenta[e][1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methylene]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound CC1=NC2=NC(\C=C/3C(N4C(=CS[C@@H]4\3)C(O)=O)=O)=NN2C2=C1CCC2 GVIJNDBUPIEBNV-VYLZPFMQSA-N 0.000 claims 2
- IAUJWOFPTCUPKI-WSVPDTOYSA-N (5r,6z)-6-{[7-(ethoxycarbonyl)-6,7,8,9-tetrahydropyrido[3,4-e][1,2,4]triazolo[1,5-a]pyrimidin-2-yl]methylene}-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C1=NC2=NC(\C=C/3C(N4C(=CS[C@@H]4\3)C(O)=O)=O)=NN2C2=C1CN(C(=O)OCC)CC2 IAUJWOFPTCUPKI-WSVPDTOYSA-N 0.000 claims 2
- WBVGDYUBKRMKNU-HMZQOCAUSA-N (5r,6z)-7-oxo-6-(5,6,7,8-tetrahydropyrazolo[5,1-b][1,3]benzoxazol-2-ylmethylidene)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C1CCCC2=C1OC1=CC(/C=C3/C(=O)N4[C@@H]3SC=C4C(=O)O)=NN12 WBVGDYUBKRMKNU-HMZQOCAUSA-N 0.000 claims 2
- YJHLAPIOTYDKSI-VYLZPFMQSA-N (5r,6z)-7-oxo-6-([1,3]thiazolo[3,2-a]benzimidazol-7-ylmethylidene)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound N1([C@@H]2SC=C1C(=O)O)C(=O)\C2=C\C(C=C12)=CC=C1N=C1N2C=CS1 YJHLAPIOTYDKSI-VYLZPFMQSA-N 0.000 claims 2
- AHICGCNKVSGCLQ-WSVPDTOYSA-N (5r,6z)-7-oxo-6-(spiro[1,3-dioxolane-2,7'-8,9-dihydro-6h-[1,2,4]triazolo[1,5-a]quinazoline]-2'-ylmethylidene)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound N1([C@@H]2SC=C1C(=O)O)C(=O)\C2=C\C(=NN1C=2CC3)N=C1N=CC=2CC13OCCO1 AHICGCNKVSGCLQ-WSVPDTOYSA-N 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 claims 2
- NPDLYUOYAGBHFB-WDSKDSINSA-N Asn-Arg Chemical compound NC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N NPDLYUOYAGBHFB-WDSKDSINSA-N 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 102000004190 Enzymes Human genes 0.000 claims 2
- 108090000790 Enzymes Proteins 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 150000003973 alkyl amines Chemical class 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 2
- 125000005325 aryloxy aryl group Chemical group 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- RLYFCCSEWJKCQN-LEPFTWFBSA-N chembl1162147 Chemical compound C1OCCC2=C1OC1=CC(/C=C3/C(=O)N4[C@@H]3SC=C4C(=O)O)=NN12 RLYFCCSEWJKCQN-LEPFTWFBSA-N 0.000 claims 2
- XFARUGBBAMTOCU-IBSXUBTNSA-N chembl1205614 Chemical compound C1CCC(SC2=N3)=C1N2C=C3/C=C1/C(=O)N2[C@@H]1SC=C2C(=O)O XFARUGBBAMTOCU-IBSXUBTNSA-N 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 2
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 2
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- GDDZRTPUGYRYNK-IZRWNGHKSA-M sodium;(5r,6z)-7-oxo-6-(5,6,7,8-tetrahydroimidazo[1,2][1,2,4]triazolo[2,4-a]pyridin-2-ylmethylidene)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound [Na+].C1CCCC2=NC3=NC(/C=C4/C(=O)N5[C@@H]4SC=C5C(=O)[O-])=CN3N21 GDDZRTPUGYRYNK-IZRWNGHKSA-M 0.000 claims 2
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- 0 C1CC*CC1 Chemical compound C1CC*CC1 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N C1CCCCC1 Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68622105P | 2005-06-01 | 2005-06-01 | |
| PCT/US2006/020410 WO2007030166A2 (en) | 2005-06-01 | 2006-05-25 | TRICYCLIC 6-ALKYLIDENE-PENEMS AS CLASS-D β-LACTAMASES INHIBITORS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008542376A JP2008542376A (ja) | 2008-11-27 |
| JP2008542376A5 true JP2008542376A5 (https=) | 2009-06-04 |
Family
ID=37836305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008514712A Withdrawn JP2008542376A (ja) | 2005-06-01 | 2006-05-25 | クラスＤのβラクタマーゼ阻害剤としての三環系６−アルキリデンペネム類 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US20060276446A1 (https=) |
| EP (1) | EP1885358A2 (https=) |
| JP (1) | JP2008542376A (https=) |
| CN (1) | CN101189010A (https=) |
| AR (1) | AR054467A1 (https=) |
| AU (1) | AU2006287938A1 (https=) |
| BR (1) | BRPI0611491A2 (https=) |
| CA (1) | CA2610478A1 (https=) |
| GT (1) | GT200600235A (https=) |
| MX (1) | MX2007015173A (https=) |
| PE (1) | PE20070010A1 (https=) |
| SV (1) | SV2007002555A (https=) |
| TW (1) | TW200716104A (https=) |
| WO (1) | WO2007030166A2 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR039475A1 (es) * | 2002-05-01 | 2005-02-23 | Wyeth Corp | 6-alquiliden-penems triciclicos como inhibidores de beta-lactamasa |
| AR039774A1 (es) * | 2002-05-01 | 2005-03-02 | Wyeth Corp | 6-alquiliden-penems biciclicos como inhibidores de beta-lactamasas |
| TW200716102A (en) * | 2005-06-01 | 2007-05-01 | Wyeth Corp | Bicyclic 6-alkylidene-penems as class-D β -lactamases inhibitors |
| US8945652B2 (en) | 2005-11-23 | 2015-02-03 | The Coca-Cola Company | High-potency sweetener for weight management and compositions sweetened therewith |
| US8524304B2 (en) * | 2005-11-23 | 2013-09-03 | The Coca-Cola Company | High-potency sweetener composition with probiotics/prebiotics and compositions sweetened therewith |
| US8512789B2 (en) * | 2005-11-23 | 2013-08-20 | The Coca-Cola Company | High-potency sweetener composition with dietary fiber and compositions sweetened therewith |
| JP2012121809A (ja) * | 2009-02-26 | 2012-06-28 | Eisai R & D Management Co Ltd | 多環式化合物の製造法およびその中間体 |
| US20110288063A1 (en) * | 2010-05-19 | 2011-11-24 | Naeja Pharmaceutical Inc. | Novel fused bridged bicyclic heteroaryl substituted 6-alkylidene penems as potent beta-lactamase inhibitors |
| CN104341345B (zh) * | 2014-10-24 | 2016-03-23 | 海门海康生物医药科技有限公司 | 一种2-甲氧基-6-酮-5,6,7,8-四氢喹啉的合成方法 |
| WO2020179859A1 (ja) | 2019-03-06 | 2020-09-10 | 第一三共株式会社 | ピロロピラゾール誘導体 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9507521A (pt) * | 1994-04-25 | 1997-09-16 | Smithkline Beecham Plc | Formulação farmacêutica método para o tratemento de infecções bacterianas em seres humanos e animais uso de uma formulação e processo para sua preparação |
| US20040132706A1 (en) * | 2001-10-05 | 2004-07-08 | Daniela Salvemini | Composition comprising a catalyst for the dismutation of superoxide and use of the composition for preventing and treating hypotension |
| AR039476A1 (es) * | 2002-05-01 | 2005-02-23 | Wyeth Corp | Proceso para preparar derivados de 6-alquiliden penem |
| AR039475A1 (es) * | 2002-05-01 | 2005-02-23 | Wyeth Corp | 6-alquiliden-penems triciclicos como inhibidores de beta-lactamasa |
| AR039774A1 (es) * | 2002-05-01 | 2005-03-02 | Wyeth Corp | 6-alquiliden-penems biciclicos como inhibidores de beta-lactamasas |
| US20040132708A1 (en) * | 2002-05-01 | 2004-07-08 | Wyeth | Process for preparing 6-alkylidene penem derivatives |
| TW200716102A (en) * | 2005-06-01 | 2007-05-01 | Wyeth Corp | Bicyclic 6-alkylidene-penems as class-D β -lactamases inhibitors |
-
2006
- 2006-05-22 TW TW095118171A patent/TW200716104A/zh unknown
- 2006-05-25 CN CNA2006800193154A patent/CN101189010A/zh active Pending
- 2006-05-25 WO PCT/US2006/020410 patent/WO2007030166A2/en not_active Ceased
- 2006-05-25 AU AU2006287938A patent/AU2006287938A1/en not_active Abandoned
- 2006-05-25 JP JP2008514712A patent/JP2008542376A/ja not_active Withdrawn
- 2006-05-25 BR BRPI0611491-1A patent/BRPI0611491A2/pt not_active IP Right Cessation
- 2006-05-25 MX MX2007015173A patent/MX2007015173A/es unknown
- 2006-05-25 CA CA002610478A patent/CA2610478A1/en not_active Abandoned
- 2006-05-25 EP EP06824758A patent/EP1885358A2/en not_active Withdrawn
- 2006-05-31 US US11/444,346 patent/US20060276446A1/en not_active Abandoned
- 2006-05-31 SV SV2006002555A patent/SV2007002555A/es unknown
- 2006-05-31 PE PE2006000563A patent/PE20070010A1/es not_active Application Discontinuation
- 2006-06-01 AR ARP060102292A patent/AR054467A1/es unknown
- 2006-06-01 GT GT200600235A patent/GT200600235A/es unknown
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