JP2012530081A5 - - Google Patents
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- Publication number
- JP2012530081A5 JP2012530081A5 JP2012515319A JP2012515319A JP2012530081A5 JP 2012530081 A5 JP2012530081 A5 JP 2012530081A5 JP 2012515319 A JP2012515319 A JP 2012515319A JP 2012515319 A JP2012515319 A JP 2012515319A JP 2012530081 A5 JP2012530081 A5 JP 2012530081A5
- Authority
- JP
- Japan
- Prior art keywords
- methylethyl
- oxy
- phenyl
- thiadiazol
- isoquinolinyl
- 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.)
- Withdrawn
Links
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- HOZSSWZKSCQQPY-UHFFFAOYSA-N 4-[6-[2-(3-cyano-4-propan-2-yloxyphenyl)-1,3-thiazol-5-yl]-5-ethyl-3,4-dihydro-1h-isoquinolin-2-yl]butanoic acid Chemical compound CCC1=C2CCN(CCCC(O)=O)CC2=CC=C1C(S1)=CN=C1C1=CC=C(OC(C)C)C(C#N)=C1 HOZSSWZKSCQQPY-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 206010025135 lupus erythematosus Diseases 0.000 claims 2
- 230000001575 pathological effect Effects 0.000 claims 2
- XBSKAZRTIYWPDS-UHFFFAOYSA-N 2-(3-chloro-4-propan-2-yloxyphenyl)-5-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)-1,3,4-thiadiazole Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NN=C(C=2C=C3CCNCCC3=CC=2)S1 XBSKAZRTIYWPDS-UHFFFAOYSA-N 0.000 claims 1
- CNWYBOVJIUYVNE-UHFFFAOYSA-N 2-(3-chloro-4-propan-2-yloxyphenyl)-5-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)-1,3-thiazole Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC=C(C=2C=C3CCNCCC3=CC=2)S1 CNWYBOVJIUYVNE-UHFFFAOYSA-N 0.000 claims 1
- PYRDBTPSMUQFPJ-UHFFFAOYSA-N 2-(3-chloro-4-propan-2-yloxyphenyl)-5-(2,3-dihydro-1h-isoindol-5-yl)-1,3,4-thiadiazole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(Cl)C(OC(C)C)=CC=C1C1=NN=C(C=2C=C3CNCC3=CC=2)S1 PYRDBTPSMUQFPJ-UHFFFAOYSA-N 0.000 claims 1
- MLDDRIFHQZBWFV-UHFFFAOYSA-N 2-propan-2-yloxy-5-[5-(1,2,3,4-tetrahydroisoquinolin-5-yl)-1,3,4-thiadiazol-2-yl]benzonitrile Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1C1=NN=C(C=2C=3CCNCC=3C=CC=2)S1 MLDDRIFHQZBWFV-UHFFFAOYSA-N 0.000 claims 1
- SAARRMVYKCRBBM-UHFFFAOYSA-N 2-propan-2-yloxy-5-[5-(1,2,3,4-tetrahydroisoquinolin-6-yl)-1,3,4-thiadiazol-2-yl]benzonitrile Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1C1=NN=C(C=2C=C3CCNCC3=CC=2)S1 SAARRMVYKCRBBM-UHFFFAOYSA-N 0.000 claims 1
- GOEKOPDTSMLSRO-UHFFFAOYSA-N 3-[5-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,3,4-thiadiazol-2-yl]-1,3-dihydroisoindol-2-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NN=C(C=2C=C3CN(CCC(O)=O)CC3=CC=2)S1 GOEKOPDTSMLSRO-UHFFFAOYSA-N 0.000 claims 1
- BFVYMCYGZXSCQF-UHFFFAOYSA-N 3-[6-[2-(3-cyano-4-propan-2-yloxyphenyl)-1,3-thiazol-5-yl]-5-ethyl-3,4-dihydro-1h-isoquinolin-2-yl]propanoic acid Chemical compound CCC1=C2CCN(CCC(O)=O)CC2=CC=C1C(S1)=CN=C1C1=CC=C(OC(C)C)C(C#N)=C1 BFVYMCYGZXSCQF-UHFFFAOYSA-N 0.000 claims 1
- HIYZNZOEFYXPOH-UHFFFAOYSA-N 3-[6-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,3,4-thiadiazol-2-yl]-5-ethyl-3,4-dihydro-1h-isoquinolin-2-yl]propanoic acid Chemical compound CCC1=C2CCN(CCC(O)=O)CC2=CC=C1C(S1)=NN=C1C1=CC=C(OC(C)C)C(Cl)=C1 HIYZNZOEFYXPOH-UHFFFAOYSA-N 0.000 claims 1
- YYSFXNOSSYJURL-UHFFFAOYSA-N 3-[6-[5-(3-cyano-4-propan-2-yloxyphenyl)-1,3,4-thiadiazol-2-yl]-5-methyl-3,4-dihydro-1h-isoquinolin-2-yl]propanoic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1C1=NN=C(C=2C(=C3CCN(CCC(O)=O)CC3=CC=2)C)S1 YYSFXNOSSYJURL-UHFFFAOYSA-N 0.000 claims 1
- KJSOQPSUYLGTOQ-UHFFFAOYSA-N 3-[6-[5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl]-5-ethyl-3,4-dihydro-1h-isoquinolin-2-yl]propanoic acid Chemical compound CCC1=C2CCN(CCC(O)=O)CC2=CC=C1C(S1)=NN=C1C1=CC=C(CC(C)C)C(C#N)=C1 KJSOQPSUYLGTOQ-UHFFFAOYSA-N 0.000 claims 1
- QGWQNVMOEUFEIR-UHFFFAOYSA-N 4-[6-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,3,4-thiadiazol-2-yl]-5-ethyl-3,4-dihydro-1h-isoquinolin-2-yl]butanoic acid Chemical compound CCC1=C2CCN(CCCC(O)=O)CC2=CC=C1C(S1)=NN=C1C1=CC=C(OC(C)C)C(Cl)=C1 QGWQNVMOEUFEIR-UHFFFAOYSA-N 0.000 claims 1
- VSMRHANQUBHRND-UHFFFAOYSA-N 4-[6-[5-(3-cyano-4-propan-2-yloxyphenyl)-1,3,4-thiadiazol-2-yl]-5-methyl-3,4-dihydro-1h-isoquinolin-2-yl]butanoic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1C1=NN=C(C=2C(=C3CCN(CCCC(O)=O)CC3=CC=2)C)S1 VSMRHANQUBHRND-UHFFFAOYSA-N 0.000 claims 1
- FMNVTIRPVUHEBF-UHFFFAOYSA-N 4-[7-[2-(3-chloro-4-propan-2-yloxyphenyl)-1,3-thiazol-5-yl]-1,2,4,5-tetrahydro-3-benzazepin-3-yl]butanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NC=C(C=2C=C3CCN(CCCC(O)=O)CCC3=CC=2)S1 FMNVTIRPVUHEBF-UHFFFAOYSA-N 0.000 claims 1
- AJWBTOCYYQDQMZ-UHFFFAOYSA-N 4-[7-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,3-thiazol-2-yl]-1,2,4,5-tetrahydro-3-benzazepin-3-yl]butanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=CN=C(C=2C=C3CCN(CCCC(O)=O)CCC3=CC=2)S1 AJWBTOCYYQDQMZ-UHFFFAOYSA-N 0.000 claims 1
- MDLAYHHUUJGHJV-UHFFFAOYSA-N 4-[7-[5-(3-cyano-4-propan-2-yloxyphenyl)-1,3,4-thiadiazol-2-yl]-1,2,4,5-tetrahydro-3-benzazepin-3-yl]butanoic acid;hydrochloride Chemical compound Cl.C1=C(C#N)C(OC(C)C)=CC=C1C1=NN=C(C=2C=C3CCN(CCCC(O)=O)CCC3=CC=2)S1 MDLAYHHUUJGHJV-UHFFFAOYSA-N 0.000 claims 1
- MHJITZGNDJOVPT-UHFFFAOYSA-N 5-(3-chloro-4-propan-2-yloxyphenyl)-2-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-yl)-1,3-thiazole Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=CN=C(C=2C=C3CCNCCC3=CC=2)S1 MHJITZGNDJOVPT-UHFFFAOYSA-N 0.000 claims 1
- LCDDMTDFELNROZ-UHFFFAOYSA-N 5-[5-(5-methyl-1,2,3,4-tetrahydroisoquinolin-6-yl)-1,3,4-thiadiazol-2-yl]-2-propan-2-yloxybenzonitrile Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1C1=NN=C(C=2C(=C3CCNCC3=CC=2)C)S1 LCDDMTDFELNROZ-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 102000011011 Sphingosine 1-phosphate receptors Human genes 0.000 claims 1
- 108050001083 Sphingosine 1-phosphate receptors Proteins 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000004069 aziridinyl group Chemical group 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 208000037976 chronic inflammation Diseases 0.000 claims 1
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 208000012947 ischemia reperfusion injury Diseases 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 201000001119 neuropathy Diseases 0.000 claims 1
- 230000007823 neuropathy Effects 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 208000019553 vascular disease Diseases 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0910691.5A GB0910691D0 (en) | 2009-06-19 | 2009-06-19 | Novel compounds |
| GB0910691.5 | 2009-06-19 | ||
| PCT/CN2010/000868 WO2010145202A1 (en) | 2009-06-19 | 2010-06-17 | Thiazole or thiadizaloe derivatives for use as sphingosine 1-phosphate 1 (s1p1) receptor agonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012530081A JP2012530081A (ja) | 2012-11-29 |
| JP2012530081A5 true JP2012530081A5 (https=) | 2013-07-18 |
Family
ID=40972522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012515319A Withdrawn JP2012530081A (ja) | 2009-06-19 | 2010-06-17 | スフィンゴシン１リン酸１（ｓ１ｐ１）受容体アゴニストとして用いるためのチアゾールまたはチアジアゾール誘導体 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20120094979A1 (https=) |
| EP (1) | EP2443112A4 (https=) |
| JP (1) | JP2012530081A (https=) |
| GB (1) | GB0910691D0 (https=) |
| WO (1) | WO2010145202A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201104153D0 (en) | 2011-03-11 | 2011-04-27 | Glaxo Group Ltd | Novel compounds |
| US9481659B2 (en) * | 2011-05-13 | 2016-11-01 | Celgene International Ii Sàrl | Selective heterocyclic sphingosine 1 phosphate receptor modulators |
| KR102069008B1 (ko) * | 2012-09-21 | 2020-02-11 | 메르크 파텐트 게엠베하 | C-c 삼중 결합을 갖는 화합물 및 액정 혼합물에서 이의 용도 |
| JP2018525429A (ja) * | 2015-08-28 | 2018-09-06 | アッヴィ・インコーポレイテッド | Ｓ１ｐ調節剤としての縮合複素環化合物 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1644367B1 (en) * | 2003-05-19 | 2015-10-14 | Novartis AG | Immunosuppressant compounds and compositions |
| EP1697333A4 (en) * | 2003-12-17 | 2009-07-08 | Merck & Co Inc | (3,4-DISUBSTITUTED) PROPANE ACID BOXYLATES AS AGONISTS OF THE S1P (EDG) RECEPTOR |
| AU2008240773B2 (en) * | 2007-04-19 | 2013-10-03 | Glaxo Group Limited | Oxadiazole substituted indazole derivatives for use as sphingosine 1-phosphate (S1P) agonists |
| JP2009249363A (ja) * | 2008-04-09 | 2009-10-29 | Astellas Pharma Inc | イソインドリン化合物 |
-
2009
- 2009-06-19 GB GBGB0910691.5A patent/GB0910691D0/en not_active Ceased
-
2010
- 2010-06-17 JP JP2012515319A patent/JP2012530081A/ja not_active Withdrawn
- 2010-06-17 WO PCT/CN2010/000868 patent/WO2010145202A1/en not_active Ceased
- 2010-06-17 EP EP10788598A patent/EP2443112A4/en not_active Withdrawn
- 2010-06-17 US US13/378,809 patent/US20120094979A1/en not_active Abandoned
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