JP2004505953A5 - - Google Patents
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- Publication number
- JP2004505953A5 JP2004505953A5 JP2002518177A JP2002518177A JP2004505953A5 JP 2004505953 A5 JP2004505953 A5 JP 2004505953A5 JP 2002518177 A JP2002518177 A JP 2002518177A JP 2002518177 A JP2002518177 A JP 2002518177A JP 2004505953 A5 JP2004505953 A5 JP 2004505953A5
- Authority
- JP
- Japan
- Prior art keywords
- ring
- alkyl
- oxo
- membered
- compound according
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 42
- 229910052799 carbon Inorganic materials 0.000 claims description 39
- -1 hydroxy, amino Chemical group 0.000 claims description 32
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 27
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000004043 oxo group Chemical group O=* 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 16
- 150000001721 carbon Chemical group 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 14
- OBUUFWIMEGVAQS-UHFFFAOYSA-N Pleuromutenol Natural products CC1C(O)C(C)(C=C)CC(O)C2(C)C(C)CCC31C2C(=O)CC3 OBUUFWIMEGVAQS-UHFFFAOYSA-N 0.000 claims description 14
- 229960002771 retapamulin Drugs 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 8
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 8
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- STZYTFJPGGDRJD-NHUWBDDWSA-N retapamulin Chemical compound C([C@H]([C@@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]2C)OC(=O)CS[C@@H]3C[C@H]4CC[C@H](N4C)C3)C)C[C@]32[C@H]1C(=O)CC3 STZYTFJPGGDRJD-NHUWBDDWSA-N 0.000 claims description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 4
- 230000000306 recurrent effect Effects 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- FHINJVLCWVXUJL-UHFFFAOYSA-N thietane-2,4-dione Chemical compound O=C1CC(=O)S1 FHINJVLCWVXUJL-UHFFFAOYSA-N 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 2
- PYEZPBWTGJYSGM-UHFFFAOYSA-N 4-oxo-1,6,7,8-tetrahydropyrimido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound N1CCCN2C(=O)C(C(=O)O)=CN=C21 PYEZPBWTGJYSGM-UHFFFAOYSA-N 0.000 claims description 2
- ONIBWKKTOPOVIA-SCSAIBSYSA-N D-Proline Chemical compound OC(=O)[C@H]1CCCN1 ONIBWKKTOPOVIA-SCSAIBSYSA-N 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- 206010033078 Otitis media Diseases 0.000 claims description 2
- 208000004210 Pressure Ulcer Diseases 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- 230000001154 acute effect Effects 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 2
- 125000005276 alkyl hydrazino group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000002648 azanetriyl group Chemical group *N(*)* 0.000 claims description 2
- 230000001580 bacterial effect Effects 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 2
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 2
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 2
- 244000144972 livestock Species 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 230000000813 microbial effect Effects 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- JOHZPMXAZQZXHR-UHFFFAOYSA-N pipemidic acid Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CN=C1N1CCNCC1 JOHZPMXAZQZXHR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 2
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 2
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 2
- UVGCYMVPDRDDDT-UHFFFAOYSA-N pyrimido[4,5-c]pyridazine Chemical compound N1=CN=C2N=NC=CC2=C1 UVGCYMVPDRDDDT-UHFFFAOYSA-N 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 201000009890 sinusitis Diseases 0.000 claims description 2
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- MSTNYGQPCMXVAQ-RYUDHWBXSA-N (6S)-5,6,7,8-tetrahydrofolic acid Chemical compound C([C@H]1CNC=2N=C(NC(=O)C=2N1)N)NC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 MSTNYGQPCMXVAQ-RYUDHWBXSA-N 0.000 claims 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 1
- 206010062255 Soft tissue infection Diseases 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 206010040872 skin infection Diseases 0.000 claims 1
- 239000005460 tetrahydrofolate Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 description 7
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical class OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0018951.4A GB0018951D0 (en) | 2000-08-03 | 2000-08-03 | Novel compounds |
| PCT/EP2001/008949 WO2002012199A1 (en) | 2000-08-03 | 2001-08-02 | Heterocyclic mutilin esters and their use as antibacterials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004505953A JP2004505953A (ja) | 2004-02-26 |
| JP2004505953A5 true JP2004505953A5 (OSRAM) | 2008-07-31 |
Family
ID=9896832
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002518177A Pending JP2004505953A (ja) | 2000-08-03 | 2001-08-02 | ヘテロ環ムチリンエステル及び抗細菌剤としてのその使用 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6878704B2 (OSRAM) |
| EP (1) | EP1309565B1 (OSRAM) |
| JP (1) | JP2004505953A (OSRAM) |
| AT (1) | ATE391715T1 (OSRAM) |
| AU (1) | AU2001291725A1 (OSRAM) |
| DE (1) | DE60133561T2 (OSRAM) |
| ES (1) | ES2304395T3 (OSRAM) |
| GB (1) | GB0018951D0 (OSRAM) |
| WO (1) | WO2002012199A1 (OSRAM) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003077656A1 (en) * | 2002-03-15 | 2003-09-25 | Ciba Specialty Chemicals Holding Inc. | 4-aminopyrimidines and their use for the antimicrobial treatment of surfaces |
| GB0207495D0 (en) | 2002-03-28 | 2002-05-08 | Biochemie Gmbh | Organic compounds |
| JP4611020B2 (ja) * | 2002-07-24 | 2011-01-12 | ナブリバ・セラピユーテイクス・アクチエンゲゼルシヤフト | 抗菌剤としてのプレウロムチリン（ｐｌｅｕｒｏｍｕｔｉｌｉｎ）誘導体 |
| GB0218578D0 (en) * | 2002-08-09 | 2002-09-18 | Glaxo Group Ltd | Novel method |
| IL151342A (en) | 2002-08-19 | 2005-06-19 | Lycored Natural Prod Ind Ltd | Industrial process for working up tomatoes and products obtained therefrom |
| GB0308114D0 (en) * | 2003-04-08 | 2003-05-14 | Glaxo Group Ltd | Novel compounds |
| JPWO2006070671A1 (ja) * | 2004-12-27 | 2008-06-12 | 杏林製薬株式会社 | １２位置換ムチリン誘導体 |
| US7442818B2 (en) * | 2006-03-14 | 2008-10-28 | David Rubin | Method of making esters and catalysts therefore |
| WO2007120877A2 (en) * | 2006-04-14 | 2007-10-25 | Qd Vision, Inc. | Transfer surface for manufacturing a light emitting device |
| US8222407B2 (en) * | 2007-05-24 | 2012-07-17 | Kyorin Pharmaceutical Co., Ltd. | Mutilin derivative having heterocyclic aromatic ring carboxylic acid structure in substituent at 14-position |
| WO2011028492A2 (en) * | 2009-08-24 | 2011-03-10 | The Regents Of The University Of California | Sortase a inhibitors |
| TW201111385A (en) | 2009-08-27 | 2011-04-01 | Biocryst Pharm Inc | Heterocyclic compounds as janus kinase inhibitors |
| CN103649070B (zh) * | 2011-07-08 | 2016-05-18 | 先正达参股股份有限公司 | 用于制备硫杂环丁胺的方法 |
| CN104803926B (zh) * | 2015-03-25 | 2017-05-03 | 中国农业科学院兰州畜牧与兽药研究所 | 一种具有嘧啶侧链的截短侧耳素衍生物及其应用 |
| CN105399684A (zh) * | 2015-11-03 | 2016-03-16 | 中国农业科学院兰州畜牧与兽药研究所 | 一种截短侧耳素类化合物、制备方法、多晶型及多晶型的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997025309A1 (en) * | 1996-01-03 | 1997-07-17 | Smithkline Beecham Plc | Carbamoyloxy derivatives of mutiline and their use as antibacterials |
| GB9817029D0 (en) * | 1998-08-05 | 1998-09-30 | Smithkline Beecham Plc | Novel compounds |
| WO2000027790A1 (en) * | 1998-11-11 | 2000-05-18 | Smithkline Beecham P.L.C. | Mutilin compounds |
| AU3036200A (en) | 1998-12-18 | 2000-07-12 | Smithkline Beecham Plc | Mutilin 14-ester derivatives having antibacterial activity |
| GB9912657D0 (en) * | 1999-06-01 | 1999-07-28 | Smithkline Beecham Plc | Novel compounds |
-
2000
- 2000-08-03 GB GBGB0018951.4A patent/GB0018951D0/en not_active Ceased
-
2001
- 2001-08-02 JP JP2002518177A patent/JP2004505953A/ja active Pending
- 2001-08-02 EP EP01971856A patent/EP1309565B1/en not_active Expired - Lifetime
- 2001-08-02 US US10/343,596 patent/US6878704B2/en not_active Expired - Fee Related
- 2001-08-02 WO PCT/EP2001/008949 patent/WO2002012199A1/en not_active Ceased
- 2001-08-02 AT AT01971856T patent/ATE391715T1/de not_active IP Right Cessation
- 2001-08-02 ES ES01971856T patent/ES2304395T3/es not_active Expired - Lifetime
- 2001-08-02 AU AU2001291725A patent/AU2001291725A1/en not_active Abandoned
- 2001-08-02 DE DE60133561T patent/DE60133561T2/de not_active Expired - Lifetime
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