JP2005527556A5 - - Google Patents
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- JP2005527556A5 JP2005527556A5 JP2003579825A JP2003579825A JP2005527556A5 JP 2005527556 A5 JP2005527556 A5 JP 2005527556A5 JP 2003579825 A JP2003579825 A JP 2003579825A JP 2003579825 A JP2003579825 A JP 2003579825A JP 2005527556 A5 JP2005527556 A5 JP 2005527556A5
- Authority
- JP
- Japan
- Prior art keywords
- independently
- compound according
- alkylene
- compound
- optionally substituted
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims 75
- 125000002947 alkylene group Chemical group 0.000 claims 33
- -1 piperazine-1,4-diyl group Chemical group 0.000 claims 15
- 125000004429 atom Chemical group 0.000 claims 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 8
- 125000000732 arylene group Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 241001465754 Metazoa Species 0.000 claims 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 3
- 102000003964 Histone deacetylase Human genes 0.000 claims 3
- 108090000353 Histone deacetylase Proteins 0.000 claims 3
- 125000001931 aliphatic group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000004452 carbocyclyl group Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 230000002062 proliferating effect Effects 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- KCOPAESEGCGTKM-UHFFFAOYSA-N 1,3-oxazol-4-one Chemical compound O=C1COC=N1 KCOPAESEGCGTKM-UHFFFAOYSA-N 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000001413 cellular effect Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- JTHRRMFZHSDGNJ-UHFFFAOYSA-N piperazine-2,3-dione Chemical compound O=C1NCCNC1=O JTHRRMFZHSDGNJ-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36933702P | 2002-04-03 | 2002-04-03 | |
| PCT/GB2003/001463 WO2003082288A1 (en) | 2002-04-03 | 2003-04-03 | Carbamic acid compounds comprising a piperazine linkage as hdac inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005527556A JP2005527556A (ja) | 2005-09-15 |
| JP2005527556A5 true JP2005527556A5 (https=) | 2006-05-25 |
| JP4606027B2 JP4606027B2 (ja) | 2011-01-05 |
Family
ID=28675576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003579825A Expired - Fee Related JP4606027B2 (ja) | 2002-04-03 | 2003-04-03 | Ｈｄａｃ阻害剤としてのピペラジン結合を有するカルバミン酸化合物 |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US7629343B2 (https=) |
| EP (1) | EP1492534B1 (https=) |
| JP (1) | JP4606027B2 (https=) |
| AT (1) | ATE399012T1 (https=) |
| AU (1) | AU2003229883B2 (https=) |
| BR (1) | BR0308908A (https=) |
| CA (1) | CA2479906C (https=) |
| DE (1) | DE60321775D1 (https=) |
| ES (1) | ES2309313T3 (https=) |
| MX (1) | MXPA04009490A (https=) |
| NO (1) | NO329942B1 (https=) |
| NZ (1) | NZ536116A (https=) |
| WO (1) | WO2003082288A1 (https=) |
Families Citing this family (79)
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| OA12793A (en) | 2002-03-13 | 2006-07-10 | Janssen Pharmaceutica Nv | Sulfonylamino-derivatives as novel inhibitors of histone deacetylase. |
| CA2479906C (en) * | 2002-04-03 | 2011-02-08 | Topotarget Uk Limited | Carbamic acid compounds comprising a piperazine linkage as hdac inhibitors |
| US7154002B1 (en) | 2002-10-08 | 2006-12-26 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
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2003
- 2003-04-03 CA CA2479906A patent/CA2479906C/en not_active Expired - Fee Related
- 2003-04-03 NZ NZ536116A patent/NZ536116A/en not_active IP Right Cessation
- 2003-04-03 AU AU2003229883A patent/AU2003229883B2/en not_active Ceased
- 2003-04-03 MX MXPA04009490A patent/MXPA04009490A/es active IP Right Grant
- 2003-04-03 EP EP03722719A patent/EP1492534B1/en not_active Expired - Lifetime
- 2003-04-03 US US10/509,732 patent/US7629343B2/en not_active Expired - Fee Related
- 2003-04-03 JP JP2003579825A patent/JP4606027B2/ja not_active Expired - Fee Related
- 2003-04-03 BR BR0308908-8A patent/BR0308908A/pt not_active IP Right Cessation
- 2003-04-03 DE DE60321775T patent/DE60321775D1/de not_active Expired - Lifetime
- 2003-04-03 ES ES03722719T patent/ES2309313T3/es not_active Expired - Lifetime
- 2003-04-03 WO PCT/GB2003/001463 patent/WO2003082288A1/en not_active Ceased
- 2003-04-03 AT AT03722719T patent/ATE399012T1/de not_active IP Right Cessation
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2004
- 2004-11-02 NO NO20044744A patent/NO329942B1/no not_active IP Right Cessation
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2008
- 2008-07-01 US US12/165,686 patent/US7981895B2/en not_active Expired - Lifetime
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2011
- 2011-07-18 US US13/184,869 patent/US20110275810A1/en not_active Abandoned
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