JP2011144183A5 - - Google Patents
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- Publication number
- JP2011144183A5 JP2011144183A5 JP2011033491A JP2011033491A JP2011144183A5 JP 2011144183 A5 JP2011144183 A5 JP 2011144183A5 JP 2011033491 A JP2011033491 A JP 2011033491A JP 2011033491 A JP2011033491 A JP 2011033491A JP 2011144183 A5 JP2011144183 A5 JP 2011144183A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- alkenyl
- heterocycle
- heteroaryl
- 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 232
- 125000000623 heterocyclic group Chemical group 0.000 claims description 61
- 125000003342 alkenyl group Chemical group 0.000 claims description 56
- 125000001072 heteroaryl group Chemical group 0.000 claims description 56
- 125000003118 aryl group Chemical group 0.000 claims description 54
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 45
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 45
- 125000000304 alkynyl group Chemical group 0.000 claims description 43
- 125000001188 haloalkyl group Chemical group 0.000 claims description 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
- -1 cycloalkenylalkyl Chemical group 0.000 claims description 33
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
- 125000004043 oxo group Chemical group O=* 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 25
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 16
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 16
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 10
- 125000004967 formylalkyl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 8
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims description 7
- 125000004686 alkyl sulfanyl alkyl group Chemical group 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 3
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 3
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 3
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 3
- 125000005182 hydroxyalkylcarbonyl group Chemical group 0.000 claims description 3
- ZUAZBUFOWFNGHG-UHFFFAOYSA-N 1-benzyl-3-[bis(methylsulfanyl)methylidene]pyridine-2,4-dione Chemical compound O=C1C(=C(SC)SC)C(=O)C=CN1CC1=CC=CC=C1 ZUAZBUFOWFNGHG-UHFFFAOYSA-N 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 22
- 150000002431 hydrogen Chemical class 0.000 claims 12
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- XTZSQOCPDRDISN-UHFFFAOYSA-N 3-[bis(methylsulfanyl)methylidene]-1-(1,3-dioxoisoindol-2-yl)quinoline-2,4-dione Chemical compound C12=CC=CC=C2C(=O)C(=C(SC)SC)C(=O)N1N1C(=O)C2=CC=CC=C2C1=O XTZSQOCPDRDISN-UHFFFAOYSA-N 0.000 claims 1
- KHWCLMYAYZYZTN-UHFFFAOYSA-N 3-[bis(methylsulfanyl)methylidene]-1-(3-methylbutyl)pyridine-2,4-dione Chemical compound CSC(SC)=C1C(=O)C=CN(CCC(C)C)C1=O KHWCLMYAYZYZTN-UHFFFAOYSA-N 0.000 claims 1
- RVSMFGSNSHGPSI-UHFFFAOYSA-N 3-[bis(methylsulfanyl)methylidene]-1-(cyclobutylamino)quinoline-2,4-dione Chemical compound C12=CC=CC=C2C(=O)C(=C(SC)SC)C(=O)N1NC1CCC1 RVSMFGSNSHGPSI-UHFFFAOYSA-N 0.000 claims 1
- JFGJNOCVZLBOHU-UHFFFAOYSA-N 3-[bis(methylsulfanyl)methylidene]-1-(cyclopropylmethylamino)quinoline-2,4-dione Chemical compound C12=CC=CC=C2C(=O)C(=C(SC)SC)C(=O)N1NCC1CC1 JFGJNOCVZLBOHU-UHFFFAOYSA-N 0.000 claims 1
- SALDWSVHHAJNFX-UHFFFAOYSA-N 3-[bis(methylsulfanyl)methylidene]-1-butyl-1,8-naphthyridine-2,4-dione Chemical compound C1=CN=C2N(CCCC)C(=O)C(=C(SC)SC)C(=O)C2=C1 SALDWSVHHAJNFX-UHFFFAOYSA-N 0.000 claims 1
- ICMGLRUYEQNHPF-UHFFFAOYSA-N Uraprene Chemical compound COC1=CC=CC=C1N1CCN(CCCNC=2N(C(=O)N(C)C(=O)C=2)C)CC1 ICMGLRUYEQNHPF-UHFFFAOYSA-N 0.000 claims 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 0 C*=C(*)N(*)C(C(C=O)=*)O Chemical compound C*=C(*)N(*)C(C(C=O)=*)O 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- OHYHOUNFCYTKFB-UHFFFAOYSA-N methyl tris(methylsulfanyl)methyl sulfate Chemical compound COS(=O)(=O)OC(SC)(SC)SC OHYHOUNFCYTKFB-UHFFFAOYSA-N 0.000 description 1
- CZMMOAYCABWKQZ-UHFFFAOYSA-N methylsulfanyl hydrogen sulfate Chemical compound CSOS(O)(=O)=O CZMMOAYCABWKQZ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/285,714 | 2002-11-01 | ||
| US10/285,714 US20040097492A1 (en) | 2002-11-01 | 2002-11-01 | Anti-infective agents |
| US10/410,853 US20040087577A1 (en) | 2002-11-01 | 2003-04-10 | Anti-infective agents |
| US10/410,853 | 2003-04-10 | ||
| US10/625,121 | 2003-07-23 | ||
| US10/625,121 US20040162285A1 (en) | 2002-11-01 | 2003-07-23 | Anti-infective agents |
| US10/679,881 | 2003-10-06 | ||
| US10/679,881 US20050075331A1 (en) | 2003-10-06 | 2003-10-06 | Anti-infective agents |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2005502238A Division JP4738172B2 (ja) | 2002-11-01 | 2003-10-31 | 抗感染薬 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011144183A JP2011144183A (ja) | 2011-07-28 |
| JP2011144183A5 true JP2011144183A5 (enExample) | 2012-05-17 |
| JP5250649B2 JP5250649B2 (ja) | 2013-07-31 |
Family
ID=43426110
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2005502238A Expired - Fee Related JP4738172B2 (ja) | 2002-11-01 | 2003-10-31 | 抗感染薬 |
| JP2011033491A Expired - Fee Related JP5250649B2 (ja) | 2002-11-01 | 2011-02-18 | 抗感染薬 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2005502238A Expired - Fee Related JP4738172B2 (ja) | 2002-11-01 | 2003-10-31 | 抗感染薬 |
Country Status (6)
| Country | Link |
|---|---|
| JP (2) | JP4738172B2 (enExample) |
| AT (1) | ATE493408T1 (enExample) |
| DE (1) | DE60335564D1 (enExample) |
| DK (1) | DK1560827T3 (enExample) |
| PT (1) | PT1560827E (enExample) |
| SI (1) | SI1560827T1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA100120C2 (en) * | 2007-04-03 | 2012-11-26 | Анадис Фармасьютикалз, Инк. | 5,6-dihydro-1h-pyridin-2-one compounds |
| GB0800855D0 (en) * | 2008-01-17 | 2008-02-27 | Syngenta Ltd | Herbicidal compounds |
| US20090257979A1 (en) * | 2008-04-15 | 2009-10-15 | Intermune, Inc. | Novel Inhibitors of Hepatitis C Virus Replication |
| WO2010049270A1 (de) * | 2008-10-29 | 2010-05-06 | Basf Se | Substituierte pyridine mit herbizider wirkung |
| CA2752443A1 (en) * | 2009-03-06 | 2010-09-10 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compounds |
| EP2560636A4 (en) * | 2010-04-23 | 2013-11-27 | Kineta Inc | ANTIVIRAL CONNECTIONS |
| US8815847B2 (en) * | 2011-06-07 | 2014-08-26 | Anadys Pharmaceuticals, Inc. | [1,2,4]thiadiazine 1,1-dioxide compounds for lowering serum uric acid |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1292310A1 (en) * | 2000-05-10 | 2003-03-19 | SmithKline Beecham Corporation | Novel anti-infectives |
| AR036081A1 (es) * | 2001-06-07 | 2004-08-11 | Smithkline Beecham Corp | Compuesto de 1,2-dihidroquinolina, su uso para preparar una composicion farmaceutica, metodos para prepararlo y compuestos del acido 2-aminobenzoico n-alquilado de utilidad como intermediarios en dichos metodos |
| WO2003059356A2 (en) * | 2001-10-30 | 2003-07-24 | Smithkline Beecham Corporation | Novel anti-infectives |
-
2003
- 2003-10-31 JP JP2005502238A patent/JP4738172B2/ja not_active Expired - Fee Related
- 2003-10-31 PT PT03768559T patent/PT1560827E/pt unknown
- 2003-10-31 DE DE60335564T patent/DE60335564D1/de not_active Expired - Lifetime
- 2003-10-31 SI SI200331953T patent/SI1560827T1/sl unknown
- 2003-10-31 AT AT03768559T patent/ATE493408T1/de active
- 2003-10-31 DK DK03768559.1T patent/DK1560827T3/da active
-
2011
- 2011-02-18 JP JP2011033491A patent/JP5250649B2/ja not_active Expired - Fee Related
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