JP2006505522A5 - - Google Patents
Download PDFInfo
- 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 (enExample) | 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 (enExample) |
| EP (1) | EP1546137A1 (enExample) |
| JP (1) | JP2006505522A (enExample) |
| KR (1) | KR20050071471A (enExample) |
| CN (1) | CN1688576A (enExample) |
| AU (1) | AU2003265348B2 (enExample) |
| BR (1) | BR0313160A (enExample) |
| CA (1) | CA2493908A1 (enExample) |
| IL (1) | IL166328A0 (enExample) |
| IS (1) | IS7657A (enExample) |
| MA (1) | MA27427A1 (enExample) |
| MX (1) | MXPA05001544A (enExample) |
| NO (1) | NO20050525L (enExample) |
| NZ (1) | NZ538134A (enExample) |
| PL (1) | PL375532A1 (enExample) |
| RU (1) | RU2296758C2 (enExample) |
| WO (1) | WO2004014899A1 (enExample) |
| ZA (1) | ZA200500864B (enExample) |
Families Citing this family (92)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6861422B2 (en) | 2003-02-26 | 2005-03-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Dihydropteridinones, processes for preparing them and their use as pharmaceutical compositions |
| MXPA06002018A (es) * | 2003-08-21 | 2006-05-31 | Osi Pharm Inc | Bencimidazolilo n-sustituidos inhibidores de c-kit. |
| WO2005037827A1 (en) * | 2003-10-16 | 2005-04-28 | Smithkline Beecham Corporation | Process for preparing benzimidazole thiophenes |
| AR046605A1 (es) * | 2003-10-27 | 2005-12-14 | S Bio Pte Ltd | Hidroxamatos unidos a biarilo; preparacion y aplicaciones farmaceuticas |
| EP1697384B1 (en) | 2003-12-18 | 2008-04-02 | Janssen Pharmaceutica N.V. | Pyrido- and pyrimidopyrimidine derivatives as anti-proliferative agents |
| JP2007519720A (ja) * | 2004-01-28 | 2007-07-19 | スミスクライン ビーチャム コーポレーション | チアゾール化合物 |
| GB0402809D0 (en) * | 2004-02-09 | 2004-03-10 | Glaxo Group Ltd | Chemical compounds |
| DE102004029784A1 (de) | 2004-06-21 | 2006-01-05 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue 2-Benzylaminodihydropteridinone, Verfahren zur deren Herstellung und deren Verwendung als Arzneimittel |
| DE102004033670A1 (de) | 2004-07-09 | 2006-02-02 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Pyridodihydropyrazinone, Verfahren zu Ihrer Herstellung und Ihre Verwendung als Arzneimittel |
| US20060074088A1 (en) | 2004-08-14 | 2006-04-06 | Boehringer Ingelheim International Gmbh | Dihydropteridinones for the treatment of cancer diseases |
| US7728134B2 (en) | 2004-08-14 | 2010-06-01 | Boehringer Ingelheim International Gmbh | Hydrates and polymorphs of 4[[(7R)-8-cyclopentyl-7-ethyl-5,6,7,8-tetrahydro-5-methyl-6-oxo-2-pteridinyl]amino]-3-methoxy-N-(1-methyl-4-piperidinyl)-benzamide, process for their manufacture and their use as medicament |
| US20060058311A1 (en) | 2004-08-14 | 2006-03-16 | Boehringer Ingelheim International Gmbh | Combinations for the treatment of diseases involving cell proliferation |
| US7759485B2 (en) | 2004-08-14 | 2010-07-20 | Boehringer Ingelheim International Gmbh | Process for the manufacture of dihydropteridinones |
| US20060035903A1 (en) | 2004-08-14 | 2006-02-16 | Boehringer Ingelheim International Gmbh | Storage stable perfusion solution for dihydropteridinones |
| EP1632493A1 (de) | 2004-08-25 | 2006-03-08 | Boehringer Ingelheim Pharma GmbH & Co.KG | Dihydropteridinonderivative, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| EP1630163A1 (de) | 2004-08-25 | 2006-03-01 | Boehringer Ingelheim Pharma GmbH & Co.KG | Dihydropteridinonderivative, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| AU2005278292B2 (en) | 2004-08-31 | 2011-09-08 | Msd K.K. | Novel substituted imidazole derivatives |
| JP4935357B2 (ja) | 2004-11-08 | 2012-05-23 | Ｍｓｄ株式会社 | 新規縮環イミダゾール誘導体 |
| DE102004058337A1 (de) | 2004-12-02 | 2006-06-14 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verfahren zur Herstellung von annelierten Piperazin-2-on Derivaten |
| NI200700147A (es) | 2004-12-08 | 2019-05-10 | Janssen Pharmaceutica Nv | Derivados de quinazolina inhibidores de cinasas dirigidos a multip |
| WO2006066172A1 (en) | 2004-12-17 | 2006-06-22 | Amgen, Inc. | Aminopyrimidine compounds and methods of use |
| AR055616A1 (es) | 2005-09-06 | 2007-08-29 | Smithkline Beecham Corp | Compuestos de tiofeno bencimidazol |
| CN101300251B (zh) * | 2005-09-06 | 2011-08-03 | 史密丝克莱恩比彻姆公司 | 作为plk抑制剂的苯并咪唑噻吩化合物 |
| EP1924572B1 (en) * | 2005-09-06 | 2009-12-30 | SmithKline Beecham Corporation | Regioselective process for preparing benzimidazole thiophenes |
| ATE459620T1 (de) * | 2005-09-06 | 2010-03-15 | Glaxosmithkline Llc | Benzimidazolthiophenverbindungen als plk- modulatoren |
| JP5498703B2 (ja) * | 2006-01-23 | 2014-05-21 | バーテックス ファーマシューティカルズ インコーポレイテッド | プロテインキナーゼのインヒビターとして有用なチオフェン−カルボキサミド |
| US7439358B2 (en) | 2006-02-08 | 2008-10-21 | Boehringer Ingelheim International Gmbh | Specific salt, anhydrous and crystalline form of a dihydropteridione derivative |
| US7504513B2 (en) * | 2006-02-27 | 2009-03-17 | Hoffman-La Roche Inc. | Thiazolyl-benzimidazoles |
| EP2418210A1 (en) | 2006-04-13 | 2012-02-15 | Vertex Pharmceuticals Incorporated | Thiophene-carboxamides useful as inhibitors of protein kinases |
| WO2007139795A1 (en) * | 2006-05-23 | 2007-12-06 | Vertex Pharmaceuticals Incorporated | Thiophene-carboxamides useful as inhibitors of protein kinases |
| JP2009538309A (ja) * | 2006-05-23 | 2009-11-05 | バーテックス ファーマシューティカルズ インコーポレイテッド | プロテインキナーゼのインヒビターとして有用なチオフェンカルボキサミド |
| JP2009539770A (ja) * | 2006-06-02 | 2009-11-19 | スミスクライン ビーチャム コーポレーション | Ｐｌｋに対する活性を有するベンゾイミダゾール置換チオフェン誘導体 |
| US7615643B2 (en) | 2006-06-02 | 2009-11-10 | Smithkline Beecham Corporation | Benzimidazole thiophene compounds |
| WO2007143506A2 (en) * | 2006-06-02 | 2007-12-13 | Smithkline Beecham Corporation | Substituted benzimidazole thiophene benzyl ether compounds |
| EP2044084B1 (en) | 2006-07-13 | 2016-02-17 | Janssen Pharmaceutica NV | Mtki quinazoline derivatives |
| US7538107B2 (en) | 2006-08-15 | 2009-05-26 | Wyeth | Oxazinan-2-one derivatives useful as PR modulators |
| WO2008021338A2 (en) | 2006-08-15 | 2008-02-21 | Wyeth | Tricyclic oxazolidone derivatives useful as pr modulators |
| WO2008021309A1 (en) | 2006-08-15 | 2008-02-21 | Wyeth | Imidazolidin-2-one derivatives useful as pr modulators |
| US7649007B2 (en) | 2006-08-15 | 2010-01-19 | Wyeth Llc | Oxazolidine derivatives as PR modulators |
| TW200815428A (en) | 2006-08-15 | 2008-04-01 | Wyeth Corp | Oxazolidone derivatives as PR modulators |
| EP2079733A2 (en) * | 2006-10-31 | 2009-07-22 | SmithKline Beecham Corporation | 5- and 6-substituted benzimidazole thiophene compounds |
| WO2008153701A1 (en) * | 2007-05-24 | 2008-12-18 | Schering Corporation | Compounds for inhibiting ksp kinesin activity |
| US8236954B2 (en) | 2007-06-26 | 2012-08-07 | Glaxosmithkline Llc | Processes for preparing benzimidazole thiophenes |
| WO2009003911A1 (en) * | 2007-06-29 | 2009-01-08 | 4Sc Ag | Thiophene-imidazopyridines |
| US8318731B2 (en) | 2007-07-27 | 2012-11-27 | Janssen Pharmaceutica Nv | Pyrrolopyrimidines |
| EP2185559A1 (en) | 2007-08-03 | 2010-05-19 | Boehringer Ingelheim International GmbH | Crystalline form of a dihydropteridione derivative |
| EP2217588A4 (en) * | 2007-11-02 | 2013-12-04 | Methylgene Inc | INHIBITORS OF HISTONE DEACETYLASE |
| WO2009094224A1 (en) | 2008-01-25 | 2009-07-30 | Millennium Pharmaceuticals, Inc. | Thiophenes and their use as phosphatidylinositol 3-kinase (pi3k) inhibitors |
| EP2100894A1 (en) | 2008-03-12 | 2009-09-16 | 4Sc Ag | Pyridopyrimidines used as Plk1 (polo-like kinase) inhibitors |
| UA103319C2 (en) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
| WO2010012745A2 (en) * | 2008-07-29 | 2010-02-04 | Boehringer Ingelheim International Gmbh | Benzimidazoles |
| JP2012512223A (ja) * | 2008-12-18 | 2012-05-31 | エフ．ホフマン−ラ ロシュ アーゲー | チアゾリル−ベンズイミダゾール類 |
| US9090601B2 (en) | 2009-01-30 | 2015-07-28 | Millennium Pharmaceuticals, Inc. | Thiazole derivatives |
| CA2750935A1 (en) | 2009-01-30 | 2010-08-12 | Millennium Pharmaceuticals, Inc. | Heteroaryls and their use as pi3k inhibitors |
| MY161598A (en) * | 2009-01-30 | 2017-04-28 | Glaxosmithkline Llc | Crystalline n-{ (1s)-2-amino-1-[(3-fluorophenyl)methyl]ethyl} -5-chloro-4-(4-chloro-1-methyl-1h-pyrazol-5-yl)-2-thiophenecarboxamide hydrochloride |
| US8796314B2 (en) | 2009-01-30 | 2014-08-05 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| CN102020643A (zh) | 2009-09-22 | 2011-04-20 | 上海恒瑞医药有限公司 | 二氢喋啶酮类衍生物、其制备方法及其在医药上的应用 |
| US20120329803A1 (en) | 2010-02-17 | 2012-12-27 | Boehringer Ingelheim International Gmbh | Dihydropteridinones, method for production and use thereof |
| PH12013500274A1 (en) | 2010-08-11 | 2013-03-04 | Millennium Pharm Inc | Heteroaryls and uses thereof |
| WO2012021611A1 (en) | 2010-08-11 | 2012-02-16 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| JP2013533318A (ja) | 2010-08-11 | 2013-08-22 | ミレニアム ファーマシューティカルズ， インコーポレイテッド | ヘテロアリールおよびその使用 |
| US8546566B2 (en) | 2010-10-12 | 2013-10-01 | Boehringer Ingelheim International Gmbh | Process for manufacturing dihydropteridinones and intermediates thereof |
| CA2814688A1 (en) | 2010-10-13 | 2012-04-19 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| US9358233B2 (en) | 2010-11-29 | 2016-06-07 | Boehringer Ingelheim International Gmbh | Method for treating acute myeloid leukemia |
| US9370535B2 (en) | 2011-05-17 | 2016-06-21 | Boehringer Ingelheim International Gmbh | Method for treatment of advanced solid tumors |
| CA3142817A1 (en) * | 2011-12-28 | 2013-07-04 | Global Blood Therapeutics, Inc. | Substituted benzaldehyde compounds and methods for their use in increasing tissue oxygenation |
| ES2790358T3 (es) | 2011-12-28 | 2020-10-27 | Global Blood Therapeutics Inc | Compuestos de heteroaril aldehído sustituido y métodos para su uso en el aumento de la oxigenación tisular |
| JP6453218B2 (ja) | 2012-08-24 | 2019-01-16 | ボード・オブ・リージエンツ，ザ・ユニバーシテイ・オブ・テキサス・システム | 疾患を治療するためのｈｉｆ活性の複素環式修飾物質 |
| EP2968299B1 (en) | 2013-03-15 | 2021-01-20 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US8952171B2 (en) | 2013-03-15 | 2015-02-10 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9458139B2 (en) | 2013-03-15 | 2016-10-04 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9422279B2 (en) | 2013-03-15 | 2016-08-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US10100043B2 (en) | 2013-03-15 | 2018-10-16 | Global Blood Therapeutics, Inc. | Substituted aldehyde compounds and methods for their use in increasing tissue oxygenation |
| US20140274961A1 (en) | 2013-03-15 | 2014-09-18 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9802900B2 (en) | 2013-03-15 | 2017-10-31 | Global Blood Therapeutics, Inc. | Bicyclic heteroaryl compounds and uses thereof for the modulation of hemoglobin |
| EP3919056B1 (en) | 2013-03-15 | 2024-08-28 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| CN112500338A (zh) * | 2013-03-15 | 2021-03-16 | 全球血液疗法股份有限公司 | 化合物及其用于调节血红蛋白的用途 |
| US10266551B2 (en) | 2013-03-15 | 2019-04-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| WO2015011236A1 (en) | 2013-07-26 | 2015-01-29 | Boehringer Ingelheim International Gmbh | Treatment of myelodysplastic syndrome |
| CN103408540B (zh) * | 2013-08-22 | 2016-05-18 | 中国药科大学 | 2-唑环取代噻吩类plk1抑制剂及其用途及其用途 |
| EP3039021A1 (en) | 2013-08-30 | 2016-07-06 | Ambit Biosciences Corporation | Biaryl acetamide compounds and methods of use thereof |
| EA202092627A1 (ru) | 2013-11-18 | 2021-09-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
| SG10201911662YA (en) | 2014-02-07 | 2020-02-27 | Global Blood Therapeutics Inc | Crystalline polymorphs of the free base of 2-hydroxy-6-((2-(1-isopropyl-1h-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyde |
| US9867831B2 (en) | 2014-10-01 | 2018-01-16 | Boehringer Ingelheim International Gmbh | Combination treatment of acute myeloid leukemia and myelodysplastic syndrome |
| EA201792028A1 (ru) | 2015-03-13 | 2018-04-30 | Форма Терапьютикс, Инк. | Альфа-цинамидные соединения и композиции как ингибиторы hdac8 |
| MA41841A (fr) | 2015-03-30 | 2018-02-06 | Global Blood Therapeutics Inc | Composés aldéhyde pour le traitement de la fibrose pulmonaire, de l'hypoxie, et de maladies auto-immunes et des tissus conjonctifs |
| HUE072191T2 (hu) | 2015-12-04 | 2025-10-28 | Global Blood Therapeutics Inc | A 2-hidoxi-6-((2-(1-izopropil-1H-pirazol-5-il)piridin-3-il)metoxi)benzaldehid adagolási rendje |
| TWI825524B (zh) | 2016-05-12 | 2023-12-11 | 美商全球血液治療公司 | 用於合成2-羥基-6-((2-(1-異丙基-1h-吡唑-5-基)-吡啶-3-基)甲氧基)苯甲醛之方法 |
| TWI778983B (zh) | 2016-10-12 | 2022-10-01 | 美商全球血液治療公司 | 包含2-羥基-6-((2-(1-異丙基-1h-吡唑-5-基)吡啶-3-基)甲氧基)-苯甲醛之片劑 |
| US11014884B2 (en) | 2018-10-01 | 2021-05-25 | Global Blood Therapeutics, Inc. | Modulators of hemoglobin |
| CR20210335A (es) | 2018-11-19 | 2021-09-14 | Global Blood Therapeutics Inc | Compuestos de 2-formil-3-hidroxifeniloximetilo capaces de modular la hemoglobina |
| CN119707936B (zh) * | 2025-02-25 | 2025-07-25 | 中南大学 | 一种2,4-二取代-5-氟嘧啶衍生物的盐的制备方法 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4859648A (en) * | 1984-12-28 | 1989-08-22 | Mobil Oil Corporation | Layered metal chalcogenides containing interspathic polymeric chalcogenides |
| FR2600000B1 (fr) * | 1986-06-13 | 1989-04-14 | Extramet Sa | Procede et dispositif de granulation d'un metal fondu |
| US4818270A (en) * | 1986-08-28 | 1989-04-04 | Monsanto Company | 2-(Heteroamino)-4,5-substituted-oxazole/thiazole compounds as herbicide antidotes, compositions and use |
| US4859684A (en) * | 1986-09-15 | 1989-08-22 | Janssen Pharmaceutica N.V. | (1H-imidazol-1-ylmethyl) substituted benzimidazole derivatives and use thereof in treating androgen dependent disorders |
| US5151424A (en) * | 1987-07-01 | 1992-09-29 | Janssen Pharmaceutica N.V. | Pharmacologically active (Bicyclic heterocyclyl)methyl and -hetero) substituted hexahydro-1H-azepines and pyrrolidines |
| US5342957A (en) * | 1988-11-29 | 1994-08-30 | Janssen Pharmaceutica N.V. | Benzimidazoles useful in treating epithelial disorders |
| US5643934A (en) * | 1991-03-28 | 1997-07-01 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz [CD]indoles |
| US5457102A (en) * | 1994-07-07 | 1995-10-10 | Janssen Pharmaceutica, N.V. | Pyrroloimidazolyl and imidazopyridinyl substituted 1H-benzimidazole derivatives |
| DE4329177A1 (de) * | 1993-08-30 | 1995-03-02 | Chemotherapeutisches Forschungsinstitut Georg Speyer Haus | Klonierung eines neuen Mitgliedes der Familie der Serin-Threonin-Kinasen |
| US5955613A (en) * | 1995-10-13 | 1999-09-21 | Neurogen Corporation | Certain pyrrolopyridine derivatives; novel CRF1 specific ligands |
| AU738304B2 (en) * | 1995-10-13 | 2001-09-13 | Neurogen Corporation | Certain pyrrolopyridine derivatives; novel CRF 1 specific ligands |
| CA2293508A1 (en) * | 1997-06-04 | 1998-12-10 | Louis Nickolaus Jungheim | Anti-viral compounds |
| US5990146A (en) * | 1997-08-20 | 1999-11-23 | Warner-Lambert Company | Benzimidazoles for inhibiting protein tyrosine kinase mediated cellular proliferation |
| US6162804A (en) * | 1997-09-26 | 2000-12-19 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| US6465484B1 (en) * | 1997-09-26 | 2002-10-15 | Merck & Co., Inc. | Angiogenesis inhibitors |
| JP3256513B2 (ja) * | 1998-02-11 | 2002-02-12 | ファイザー製薬株式会社 | ベンゾイミダゾールシクロオキシゲナーゼ−２阻害剤 |
| US6358738B1 (en) * | 1998-05-13 | 2002-03-19 | The President And Fellows Of Harvard College | Polo box therapeutic compositions, methods, and uses therefor |
| AU754050B2 (en) * | 1998-07-16 | 2002-10-31 | Sanofi-Aventis Deutschland Gmbh | Phosphinous and phosphonic acid derivatives used as medicaments |
| CA2341409A1 (en) * | 1998-08-31 | 2000-03-09 | Merck And Co., Inc. | Novel angiogenesis inhibitors |
| GB9914825D0 (en) * | 1999-06-24 | 1999-08-25 | Smithkline Beecham Spa | Novel compounds |
| US6642425B2 (en) * | 2002-03-05 | 2003-11-04 | Sasol North America Inc. | Reactive distillation process for the alkylation of aromatic hydrocarbons |
| US20040002524A1 (en) * | 2002-06-24 | 2004-01-01 | Richard Chesworth | Benzimidazole compounds and their use as estrogen agonists/antagonists |
-
2003
- 2003-08-04 BR BR0313160-2A patent/BR0313160A/pt not_active IP Right Cessation
- 2003-08-04 RU RU2005102390/04A patent/RU2296758C2/ru not_active IP Right Cessation
- 2003-08-04 CN CNA038237555A patent/CN1688576A/zh active Pending
- 2003-08-04 MX MXPA05001544A patent/MXPA05001544A/es unknown
- 2003-08-04 EP EP03784888A patent/EP1546137A1/en not_active Ceased
- 2003-08-04 AU AU2003265348A patent/AU2003265348B2/en not_active Ceased
- 2003-08-04 KR KR1020057002244A patent/KR20050071471A/ko not_active Ceased
- 2003-08-04 CA CA002493908A patent/CA2493908A1/en not_active Abandoned
- 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 PL PL03375532A patent/PL375532A1/xx not_active Application Discontinuation
- 2003-08-04 US US10/522,958 patent/US20060074119A1/en not_active Abandoned
-
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