JP2006505522A5 - - Google Patents
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- Publication number
- JP2006505522A5 JP2006505522A5 JP2004527723A JP2004527723A JP2006505522A5 JP 2006505522 A5 JP2006505522 A5 JP 2006505522A5 JP 2004527723 A JP2004527723 A JP 2004527723A JP 2004527723 A JP2004527723 A JP 2004527723A JP 2006505522 A5 JP2006505522 A5 JP 2006505522A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- benzimidazol
- oxy
- thiophene
- carboxamide
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- -1 and -N 3 R 5 is H Chemical group 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims description 5
- 125000006713 (C5-C10) cycloalkyl group Chemical group 0.000 claims description 3
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 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 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 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
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000004419 alkynylene group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- JSKUWFIZUALZLX-UHFFFAOYSA-N 5-(5,6-dimethoxy-1-benzimidazolyl)-3-[[2-(trifluoromethyl)phenyl]methoxy]-2-thiophenecarboxamide Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C(N)=O)=CC=1OCC1=CC=CC=C1C(F)(F)F JSKUWFIZUALZLX-UHFFFAOYSA-N 0.000 claims 1
- PEYXQVLQDBAPGS-UHFFFAOYSA-N 5-(5-aminobenzimidazol-1-yl)-3-[1-(2-chlorophenyl)ethoxy]thiophene-2-carboxamide Chemical compound C1=C(N2C3=CC=C(N)C=C3N=C2)SC(C(N)=O)=C1OC(C)C1=CC=CC=C1Cl PEYXQVLQDBAPGS-UHFFFAOYSA-N 0.000 claims 1
- ITAJXWHXKVYGCF-UHFFFAOYSA-N 5-(benzimidazol-1-yl)-3-[[2-(trifluoromethyl)phenyl]methoxy]thiophene-2-carboxamide Chemical compound NC(=O)C=1SC(N2C3=CC=CC=C3N=C2)=CC=1OCC1=CC=CC=C1C(F)(F)F ITAJXWHXKVYGCF-UHFFFAOYSA-N 0.000 claims 1
- GZQFYXXEKUGSDK-UHFFFAOYSA-N 5-[5-methoxy-6-(2-morpholin-4-ylethoxy)benzimidazol-1-yl]-3-[[2-(trifluoromethyl)phenyl]methoxy]thiophene-2-carboxamide Chemical compound C1=2C=C(OCCN3CCOCC3)C(OC)=CC=2N=CN1C(SC=1C(N)=O)=CC=1OCC1=CC=CC=C1C(F)(F)F GZQFYXXEKUGSDK-UHFFFAOYSA-N 0.000 claims 1
- GQCQDDNYYSRXJL-UHFFFAOYSA-N 5-[5-methoxy-6-[2-(4-methylpiperazin-1-yl)ethoxy]benzimidazol-1-yl]-3-[[2-(trifluoromethyl)phenyl]methoxy]thiophene-2-carboxamide Chemical compound C1=2C=C(OCCN3CCN(C)CC3)C(OC)=CC=2N=CN1C(SC=1C(N)=O)=CC=1OCC1=CC=CC=C1C(F)(F)F GQCQDDNYYSRXJL-UHFFFAOYSA-N 0.000 claims 1
- YEXNALRMYMPINB-UHFFFAOYSA-N 5-[6-(piperidin-4-ylmethoxy)benzimidazol-1-yl]-3-[[2-(trifluoromethyl)phenyl]methoxy]thiophene-2-carboxamide Chemical compound NC(=O)C=1SC(N2C3=CC(OCC4CCNCC4)=CC=C3N=C2)=CC=1OCC1=CC=CC=C1C(F)(F)F YEXNALRMYMPINB-UHFFFAOYSA-N 0.000 claims 1
- KRMSSGBQVGFASL-UHFFFAOYSA-N 5-[6-[3-(dimethylamino)propoxy]-5-methoxybenzimidazol-1-yl]-3-[[2-(trifluoromethyl)phenyl]methoxy]thiophene-2-carboxamide Chemical compound C1=2C=C(OCCCN(C)C)C(OC)=CC=2N=CN1C(SC=1C(N)=O)=CC=1OCC1=CC=CC=C1C(F)(F)F KRMSSGBQVGFASL-UHFFFAOYSA-N 0.000 claims 1
- RWSYDQSMNZDHSF-UHFFFAOYSA-N 5-[6-methoxy-5-[3-(2-oxopyrrolidin-1-yl)propoxy]benzimidazol-1-yl]-3-[[2-(trifluoromethyl)phenyl]methoxy]thiophene-2-carboxamide Chemical compound COC1=CC=2N(C=3SC(=C(OCC=4C(=CC=CC=4)C(F)(F)F)C=3)C(N)=O)C=NC=2C=C1OCCCN1CCCC1=O RWSYDQSMNZDHSF-UHFFFAOYSA-N 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- SQQWBSBBCSFQGC-JLHYYAGUSA-N ubiquinone-2 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CCC=C(C)C)=C(C)C1=O SQQWBSBBCSFQGC-JLHYYAGUSA-N 0.000 claims 1
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- KFJQMZJQSHCCFU-UHFFFAOYSA-N 5-(5,6-dimethoxybenzimidazol-1-yl)-3-hydroxythiophene-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=2C=C(OC)C(OC)=CC=2N=CN1C1=CC(O)=C(C(N)=O)S1 KFJQMZJQSHCCFU-UHFFFAOYSA-N 0.000 description 1
- JGIPUSNBUAZWRF-UHFFFAOYSA-N 5-(5-hydroxybenzimidazol-1-yl)-3-[(2-methylphenyl)methoxy]thiophene-2-carboxylic acid Chemical compound CC1=CC=CC=C1COC1=C(C(O)=O)SC(N2C3=CC=C(O)C=C3N=C2)=C1 JGIPUSNBUAZWRF-UHFFFAOYSA-N 0.000 description 1
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
- UHCHLTQBLNUYRT-UHFFFAOYSA-N CC(c(cccc1)c1Cl)Oc1c(C(N)=O)[s]c(-[n]2c(cc(c(OC)c3)OC)c3nc2)c1 Chemical compound CC(c(cccc1)c1Cl)Oc1c(C(N)=O)[s]c(-[n]2c(cc(c(OC)c3)OC)c3nc2)c1 UHCHLTQBLNUYRT-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40200802P | 2002-08-08 | 2002-08-08 | |
| PCT/US2003/024272 WO2004014899A1 (en) | 2002-08-08 | 2003-08-04 | Thiophene compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006505522A JP2006505522A (ja) | 2006-02-16 |
| JP2006505522A5 true JP2006505522A5 (https=) | 2006-07-13 |
Family
ID=31715769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004527723A Pending JP2006505522A (ja) | 2002-08-08 | 2003-08-04 | チオフェン化合物 |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US20060074119A1 (https=) |
| EP (1) | EP1546137A1 (https=) |
| JP (1) | JP2006505522A (https=) |
| KR (1) | KR20050071471A (https=) |
| CN (1) | CN1688576A (https=) |
| AU (1) | AU2003265348B2 (https=) |
| BR (1) | BR0313160A (https=) |
| CA (1) | CA2493908A1 (https=) |
| IL (1) | IL166328A0 (https=) |
| IS (1) | IS7657A (https=) |
| MA (1) | MA27427A1 (https=) |
| MX (1) | MXPA05001544A (https=) |
| NO (1) | NO20050525L (https=) |
| NZ (1) | NZ538134A (https=) |
| PL (1) | PL375532A1 (https=) |
| RU (1) | RU2296758C2 (https=) |
| WO (1) | WO2004014899A1 (https=) |
| ZA (1) | ZA200500864B (https=) |
Families Citing this family (92)
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-
2003
- 2003-08-04 MX MXPA05001544A patent/MXPA05001544A/es unknown
- 2003-08-04 AU AU2003265348A patent/AU2003265348B2/en not_active Ceased
- 2003-08-04 BR BR0313160-2A patent/BR0313160A/pt not_active IP Right Cessation
- 2003-08-04 US US10/522,958 patent/US20060074119A1/en not_active Abandoned
- 2003-08-04 CA CA002493908A patent/CA2493908A1/en not_active Abandoned
- 2003-08-04 KR KR1020057002244A patent/KR20050071471A/ko not_active Ceased
- 2003-08-04 RU RU2005102390/04A patent/RU2296758C2/ru not_active IP Right Cessation
- 2003-08-04 PL PL03375532A patent/PL375532A1/xx not_active Application Discontinuation
- 2003-08-04 EP EP03784888A patent/EP1546137A1/en not_active Ceased
- 2003-08-04 NZ NZ538134A patent/NZ538134A/en unknown
- 2003-08-04 JP JP2004527723A patent/JP2006505522A/ja active Pending
- 2003-08-04 WO PCT/US2003/024272 patent/WO2004014899A1/en not_active Ceased
- 2003-08-04 CN CNA038237555A patent/CN1688576A/zh active Pending
-
2005
- 2005-01-17 IL IL16632805A patent/IL166328A0/xx unknown
- 2005-01-20 IS IS7657A patent/IS7657A/is unknown
- 2005-01-28 ZA ZA200500864A patent/ZA200500864B/en unknown
- 2005-01-31 NO NO20050525A patent/NO20050525L/no not_active Application Discontinuation
- 2005-03-04 MA MA28130A patent/MA27427A1/fr unknown
-
2008
- 2008-05-01 US US12/113,224 patent/US20080269298A1/en not_active Abandoned
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