HUP0300359A2 - 2-Benzotiazolil-karbamid-származékok és protein kináz inhibitorként történő felhasználásuk és ezeket tartalmazó gyógyszerkészítmények - Google Patents
2-Benzotiazolil-karbamid-származékok és protein kináz inhibitorként történő felhasználásuk és ezeket tartalmazó gyógyszerkészítményekInfo
- Publication number
- HUP0300359A2 HUP0300359A2 HU0300359A HUP0300359A HUP0300359A2 HU P0300359 A2 HUP0300359 A2 HU P0300359A2 HU 0300359 A HU0300359 A HU 0300359A HU P0300359 A HUP0300359 A HU P0300359A HU P0300359 A2 HUP0300359 A2 HU P0300359A2
- Authority
- HU
- Hungary
- Prior art keywords
- heterocyclic
- alkyl
- aryl
- group
- alkenyl
- Prior art date
Links
- -1 2-benzothiazolyl urea derivatives Chemical class 0.000 title abstract 7
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 239000003909 protein kinase inhibitor Substances 0.000 title 1
- 229910052799 carbon Inorganic materials 0.000 abstract 4
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 125000000304 alkynyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000005343 heterocyclic alkyl group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 239000000651 prodrug Substances 0.000 abstract 2
- 229940002612 prodrug Drugs 0.000 abstract 2
- 101100006370 Arabidopsis thaliana CHX2 gene Proteins 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 101000687911 Homo sapiens Transcription factor SOX-3 Proteins 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 102000009516 Protein Serine-Threonine Kinases Human genes 0.000 abstract 1
- 108010009341 Protein Serine-Threonine Kinases Proteins 0.000 abstract 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 abstract 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 abstract 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 abstract 1
- 239000004473 Threonine Substances 0.000 abstract 1
- 102100024276 Transcription factor SOX-3 Human genes 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 230000033115 angiogenesis Effects 0.000 abstract 1
- 125000005018 aryl alkenyl group Chemical group 0.000 abstract 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 abstract 1
- 125000005015 aryl alkynyl group Chemical group 0.000 abstract 1
- 125000001769 aryl amino group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 201000011510 cancer Diseases 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 230000003463 hyperproliferative effect Effects 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 229910052717 sulfur Chemical group 0.000 abstract 1
- 239000011593 sulfur Chemical group 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 abstract 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 abstract 1
Classifications
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- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
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Abstract
A találmány tárgya (I) általános képletű 2-benzotiazolilkarbamid-származékok, racém-diasztereomer elegyei, optikailag aktív izomerjei,prodrugjai, izotópjai vagy gyógyászatilag elfogadható sói, ezekizomerjei, prodrugjai és izotópjai, ahol a szubsztituensek jelentéseaz alábbiakban megadott. A találmány szerinti vegyületekszerin/treonin és tirozin kináz inhibitorként hasznosíthatók.Különösen hasznosak olyan tirozin kinázok inhibitoraiként, amelyek atúlburjánzásos betegségek, különösen a rák, valamint az angiogenezisfolyamatában fontosak. A találmány kiterjed a vegyületeket tartalmazógyógyszerkészítményekre is. Q jelentése hidrogénatom vagyvegyértékvonal, amely X1-gyel együtt és a két nitrogénatommal együtt,amelyekhez Q és X1 kapcsolódik, és a C=Y csoporttal együtt, melyhez akét nitrogénatom kapcsolódik a) képletű csoportot képezhet, ahol Q1jelentése 1-6 szénatomos alkilcsoport; Y jelentése oxigén- vagykénatom; W jelentése hidrogén-, klór-, bróm-, jódatom, nitro-, ciano-,SCN, OCF3, -Xq-(C(R10)2)a-Y1q-(C(R10)2)a-Z1q képletű csoport vagyadott esetben szubsztituált alkil-, alkenil-, alkinil-, heterociklusosalkenil- vagy heterociklusos alkinilcsoport, R1 és R2 egymástólfüggetlenül hidrogén- vagy halogénatom, hidroxil-, nitro-,cianocsoport, vagy COOH, COOX3, SX3, SO2X3, SOX3, C(O)X3, NHC(O)X3,C(O)NHX3, NHSO2X3 vagy adott esetben szubsztituált alkil-, alkenil-,alkinil-, alkoxi-, aminocsoport, NHX3, NX3X3, alkil-amino-, aril-amino-, heterociklusos amino-, alkil-tio-, alkil-szulfanáto-, aril-,aril-oxi-, aril-alkil-, aril-alkenil-, aril-alkinil-, aril-alkoxi-,heterociklusos, heterociklusos oxi-, heterociklusos alkil-,heterociklusos alkenil-, heterociklusos alkinil-, heterociklusosalkoxi-, heterociklusos tio-, heterociklusos szulfinil-,heterociklusos szulfonil-, cikloalkil- vagy -(CH2)m-(CHX2)CN- csoport;R3 jelentése hidrogénatom vagy adott esetben szubsztituált karbonil-,alkil-, alkenil-, alkinil-, cikloalkil-, aril-, aril-alkil-,heterociklusos, heterociklusos alkil-, heterociklusos heterociklus,heterociklusos cikloalkil-, amino-, alkil-amino-, aril-amino-,alkoxi-, tio-alkoxi- vagy acilcsoport; vagy R3 és X1 a nitrogénatommalegyütt, melyhez kapcsolódik, képezhet f), g) vagy h) képletűcsoportot, ahol Z minden esetben egymástól függetlenül lehet oxo- vagyadott esetben szubsztituált -C(O)-(1-6 szénatomos alkil)-, -C(O)aril-,-C(O)N-(1-6 szénatomos alkil)-, -C(O)N-aril-, 1-6 szénatomos alkil-,2-6 szénatomos alkenil-, 2-6 szénatomos alkinil-, amino-, mono- vagydi-1-6 szénatomos alkil-amino-, -COO-(1-6 szénatomos alkil)-,piridil-, fenil-, fenil-(1-6 szénatomos alkil)- vagy fenil-(1-6szénatomos alkenil)-csoport. Ó
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US18084100P | 2000-02-07 | 2000-02-07 | |
PCT/US2001/003803 WO2001057008A1 (en) | 2000-02-07 | 2001-02-06 | 2-benzothiazolyl urea derivatives and their use as protein kinase inhibitors |
Publications (1)
Publication Number | Publication Date |
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HUP0300359A2 true HUP0300359A2 (hu) | 2003-06-28 |
Family
ID=22661941
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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HU0300359A HUP0300359A2 (hu) | 2000-02-07 | 2001-02-06 | 2-Benzotiazolil-karbamid-származékok és protein kináz inhibitorként történő felhasználásuk és ezeket tartalmazó gyógyszerkészítmények |
Country Status (18)
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US (1) | US7091227B2 (hu) |
EP (1) | EP1254123A1 (hu) |
JP (1) | JP2003521543A (hu) |
KR (1) | KR20020084116A (hu) |
CN (1) | CN1422262A (hu) |
AR (1) | AR030189A1 (hu) |
AU (1) | AU2001236698A1 (hu) |
BG (1) | BG107062A (hu) |
BR (1) | BR0108085A (hu) |
CA (1) | CA2398754A1 (hu) |
HU (1) | HUP0300359A2 (hu) |
IL (1) | IL151045A0 (hu) |
MX (1) | MXPA02007632A (hu) |
NO (1) | NO20023713L (hu) |
PL (1) | PL357099A1 (hu) |
SK (1) | SK12712002A3 (hu) |
WO (1) | WO2001057008A1 (hu) |
ZA (1) | ZA200206235B (hu) |
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FR2933982A1 (fr) * | 2008-07-18 | 2010-01-22 | Sanofi Aventis | Nouveaux derives imidazo°1,2-a!pyrimidine, leur procede de preparation, leur application a titre de medicaments, compositions pharmaceutiques et nouvelle utilisation notamment comme inhibiteurs de met |
FR2933981A1 (fr) * | 2008-07-18 | 2010-01-22 | Sanofi Aventis | NOUVEAUX DERIVES IMIDAZO°1,2-a!PYRIDINE, LEUR PROCEDE DE PREPARATION, LEUR APPLICATION A TITRE DE MEDICAMENTS, COMPOSITIONS PHARMACEUTIQUES ET NOUVELLE UTILISATION NOTAMMENT COMME INHIBITEURS DE MET |
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- 2001-02-06 JP JP2001556858A patent/JP2003521543A/ja not_active Withdrawn
- 2001-02-06 EP EP01908878A patent/EP1254123A1/en not_active Withdrawn
- 2001-02-06 BR BR0108085-7A patent/BR0108085A/pt not_active Application Discontinuation
- 2001-02-06 AU AU2001236698A patent/AU2001236698A1/en not_active Abandoned
- 2001-02-06 MX MXPA02007632A patent/MXPA02007632A/es unknown
- 2001-02-06 IL IL15104501A patent/IL151045A0/xx unknown
- 2001-02-06 HU HU0300359A patent/HUP0300359A2/hu unknown
- 2001-02-06 CN CN01807734A patent/CN1422262A/zh active Pending
- 2001-02-06 SK SK1271-2002A patent/SK12712002A3/sk unknown
- 2001-02-06 KR KR1020027010188A patent/KR20020084116A/ko not_active Application Discontinuation
- 2001-02-06 CA CA002398754A patent/CA2398754A1/en not_active Abandoned
- 2001-02-06 US US09/777,554 patent/US7091227B2/en not_active Expired - Lifetime
- 2001-02-06 WO PCT/US2001/003803 patent/WO2001057008A1/en not_active Application Discontinuation
- 2001-02-06 PL PL01357099A patent/PL357099A1/xx not_active Application Discontinuation
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- 2002-08-06 NO NO20023713A patent/NO20023713L/no not_active Application Discontinuation
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WO2001057008A1 (en) | 2001-08-09 |
IL151045A0 (en) | 2003-04-10 |
NO20023713L (no) | 2002-10-04 |
US20030153568A1 (en) | 2003-08-14 |
BG107062A (bg) | 2003-04-30 |
EP1254123A1 (en) | 2002-11-06 |
US7091227B2 (en) | 2006-08-15 |
JP2003521543A (ja) | 2003-07-15 |
KR20020084116A (ko) | 2002-11-04 |
SK12712002A3 (sk) | 2003-02-04 |
CA2398754A1 (en) | 2001-08-09 |
NO20023713D0 (no) | 2002-08-06 |
AR030189A1 (es) | 2003-08-13 |
CN1422262A (zh) | 2003-06-04 |
BR0108085A (pt) | 2003-03-18 |
ZA200206235B (en) | 2004-02-13 |
PL357099A1 (en) | 2004-07-12 |
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