JP2008527013A5 - - Google Patents
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- Publication number
- JP2008527013A5 JP2008527013A5 JP2007551575A JP2007551575A JP2008527013A5 JP 2008527013 A5 JP2008527013 A5 JP 2008527013A5 JP 2007551575 A JP2007551575 A JP 2007551575A JP 2007551575 A JP2007551575 A JP 2007551575A JP 2008527013 A5 JP2008527013 A5 JP 2008527013A5
- Authority
- JP
- Japan
- Prior art keywords
- ring
- alkyl
- aryl
- het
- unsubstituted
- 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
- -1 benzimidazolinyl Chemical group 0.000 claims 59
- 125000003118 aryl group Chemical group 0.000 claims 44
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 39
- 125000000217 alkyl group Chemical group 0.000 claims 38
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 36
- 229910052736 halogen Inorganic materials 0.000 claims 18
- 150000002367 halogens Chemical class 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000004432 carbon atom Chemical group C* 0.000 claims 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 10
- 229910052731 fluorine Inorganic materials 0.000 claims 9
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000001544 thienyl group Chemical group 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 6
- 229910052794 bromium Inorganic materials 0.000 claims 6
- 125000002541 furyl group Chemical group 0.000 claims 6
- 125000001624 naphthyl group Chemical group 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000004434 sulfur atom Chemical group 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims 5
- 125000000335 thiazolyl group Chemical group 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 4
- 125000004193 piperazinyl group Chemical group 0.000 claims 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 3
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000005936 piperidyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims 2
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims 2
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 2
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 2
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims 2
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims 2
- 125000005955 1H-indazolyl group Chemical group 0.000 claims 2
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims 2
- 125000002785 azepinyl group Chemical group 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000004069 aziridinyl group Chemical group 0.000 claims 2
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 2
- 125000004623 carbolinyl group Chemical group 0.000 claims 2
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 2
- 125000000532 dioxanyl group Chemical group 0.000 claims 2
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000003838 furazanyl group Chemical group 0.000 claims 2
- 125000002636 imidazolinyl group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims 2
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims 2
- 125000005438 isoindazolyl group Chemical group 0.000 claims 2
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 2
- 125000003965 isoxazolidinyl group Chemical group 0.000 claims 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 2
- 125000004930 octahydroisoquinolinyl group Chemical group C1(NCCC2CCCC=C12)* 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims 2
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000002755 pyrazolinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 2
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 2
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 2
- 125000004306 triazinyl group Chemical group 0.000 claims 2
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims 2
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims 1
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 1
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims 1
- GYRPUQFEXCKEAV-UHFFFAOYSA-N 5-[4-(4-chlorophenyl)phenyl]sulfonyl-3,3a,4,6,7,7a-hexahydro-2h-furo[3,2-c]pyridine-4-carboxylic acid Chemical compound OC(=O)C1C2CCOC2CCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1 GYRPUQFEXCKEAV-UHFFFAOYSA-N 0.000 claims 1
- HFJKXRSYTVCITO-UHFFFAOYSA-N 5-[4-(4-cyanophenoxy)phenyl]sulfonyl-3,3a,4,6,7,7a-hexahydro-2h-furo[3,2-c]pyridine-4-carboxylic acid Chemical compound OC(=O)C1C2CCOC2CCN1S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(C#N)C=C1 HFJKXRSYTVCITO-UHFFFAOYSA-N 0.000 claims 1
- ZVWSCKYOZATDEW-UHFFFAOYSA-N 5-[4-(4-fluorophenoxy)phenyl]sulfonyl-3,3a,4,6,7,7a-hexahydro-2h-furo[3,2-c]pyridine-4-carboxylic acid Chemical compound OC(=O)C1C2CCOC2CCN1S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(F)C=C1 ZVWSCKYOZATDEW-UHFFFAOYSA-N 0.000 claims 1
- YYJXSGRCSXIZNH-UHFFFAOYSA-N 5-[4-(4-methylsulfonylphenoxy)phenyl]sulfonyl-3,3a,4,6,7,7a-hexahydro-2h-furo[3,2-c]pyridine-4-carboxylic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC1=CC=C(S(=O)(=O)N2C(C3CCOC3CC2)C(O)=O)C=C1 YYJXSGRCSXIZNH-UHFFFAOYSA-N 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims 1
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004932 phenoxathinyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005002500A DE102005002500A1 (de) | 2005-01-19 | 2005-01-19 | Tetrahydrofuranderivate als Inhibitoren von Matrix-Metalloproteinasen |
| DE102005002500.5 | 2005-01-19 | ||
| PCT/EP2006/000047 WO2006077013A1 (de) | 2005-01-19 | 2006-01-05 | Tetrahydrofuranderivate als inhibitoren von matrix-metalloproteinasen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008527013A JP2008527013A (ja) | 2008-07-24 |
| JP2008527013A5 true JP2008527013A5 (https=) | 2009-02-19 |
| JP4886704B2 JP4886704B2 (ja) | 2012-02-29 |
Family
ID=36124055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007551575A Expired - Fee Related JP4886704B2 (ja) | 2005-01-19 | 2006-01-05 | マトリックスメタロプロテイナーゼ阻害剤として使用するためのテトラヒドロフラン誘導体 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8039481B2 (https=) |
| EP (1) | EP1841772B1 (https=) |
| JP (1) | JP4886704B2 (https=) |
| KR (1) | KR101315788B1 (https=) |
| CN (1) | CN101107252B (https=) |
| AU (1) | AU2006207701B2 (https=) |
| BR (1) | BRPI0606493A2 (https=) |
| CA (1) | CA2601357C (https=) |
| DE (1) | DE102005002500A1 (https=) |
| IL (1) | IL184527A (https=) |
| MX (1) | MX2007008427A (https=) |
| WO (1) | WO2006077013A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR057959A1 (es) * | 2005-12-01 | 2007-12-26 | Elan Pharm Inc | 5-pirazolpiperidinas-(sustituidas) |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2164914C2 (ru) | 1995-11-13 | 2001-04-10 | Хехст Акциенгезелльшафт | ЦИКЛИЧЕСКИЕ И ГЕТЕРОЦИКЛИЧЕСКИЕ N-ЗАМЕЩЕННЫЕ α-ИМИНОГИДРОКСАМОВЫЕ И КАРБОНОВЫЕ КИСЛОТЫ |
| FR2748026B1 (fr) * | 1996-04-26 | 1998-06-05 | Adir | Nouveaux inhibiteurs de metalloproteases, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US5868587A (en) * | 1997-02-20 | 1999-02-09 | The Whitaker Corporation | Component mounting device |
| AU8766498A (en) * | 1997-08-04 | 1999-02-22 | Amgen, Inc. | Hydroxamic acid substituted fused heterocyclic metalloproteinase inhibitors |
| FR2795730B1 (fr) | 1999-07-01 | 2001-08-31 | Adir | Nouveaux inhibiteurs de metalloproteases, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2818643B1 (fr) * | 2000-12-22 | 2003-02-07 | Servier Lab | Nouveaux inhibiteurs de metalloproteases, leur procede de preparation et les compositions pharmaceutiques que les contiennent |
| FR2825705B1 (fr) | 2001-06-08 | 2005-05-20 | Aventis Pharma Sa | Nouveaux composes heterocycliques, leur preparation et leur utilisation comme medicaments, notamment comme anti-bacteriens |
| WO2003016248A2 (en) * | 2001-08-17 | 2003-02-27 | Bristol-Myers Squibb Company Patent Department | Bicyclic hydroxamates as inhibitors of matrix metalloproteinases and/or tnf-$g(a) converting enzyme (tace) |
| DE10209299A1 (de) * | 2002-03-02 | 2003-09-18 | Aventis Pharma Gmbh | Cyclische N-substituierte alpha-Iminocarbonsäuren zur selektiven Inhibierung von Kollagenase |
| CN1187332C (zh) * | 2002-04-26 | 2005-02-02 | 中国科学院上海有机化学研究所 | 四氢异喹啉羟肟酸磺酰胺类化合物、合成方法及其用途 |
| US7205315B2 (en) | 2003-09-27 | 2007-04-17 | Sanofi-Aventis Deutschland Gmbh | Bicyclic imino acid derivatives as inhibitors of matrix metalloproteinases |
| DE10344936A1 (de) * | 2003-09-27 | 2005-04-21 | Aventis Pharma Gmbh | Bicyclische Iminosäurederivate als Inhibitoren von Matrix-Metalloproteinasen |
| DE102004031620A1 (de) | 2004-06-30 | 2006-02-02 | Sanofi-Aventis Deutschland Gmbh | 4-Trifluormethoxyphenoxybenzol-4`-sulfonsäuren, Verfahren zu ihrer Herstellung und Verwendung in Arzneimitteln |
-
2005
- 2005-01-19 DE DE102005002500A patent/DE102005002500A1/de not_active Withdrawn
-
2006
- 2006-01-05 WO PCT/EP2006/000047 patent/WO2006077013A1/de not_active Ceased
- 2006-01-05 KR KR1020077016588A patent/KR101315788B1/ko not_active Expired - Fee Related
- 2006-01-05 JP JP2007551575A patent/JP4886704B2/ja not_active Expired - Fee Related
- 2006-01-05 AU AU2006207701A patent/AU2006207701B2/en not_active Ceased
- 2006-01-05 BR BRPI0606493-0A patent/BRPI0606493A2/pt not_active IP Right Cessation
- 2006-01-05 EP EP20060700401 patent/EP1841772B1/de not_active Expired - Lifetime
- 2006-01-05 MX MX2007008427A patent/MX2007008427A/es active IP Right Grant
- 2006-01-05 CN CN200680002746XA patent/CN101107252B/zh not_active Expired - Fee Related
- 2006-01-05 CA CA2601357A patent/CA2601357C/en not_active Expired - Fee Related
-
2007
- 2007-07-10 IL IL184527A patent/IL184527A/en not_active IP Right Cessation
- 2007-07-13 US US11/777,324 patent/US8039481B2/en not_active Expired - Fee Related
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