RU2340612C2 - 2-имидазобензотиазолы как лиганды аденозинового рецептора - Google Patents
2-имидазобензотиазолы как лиганды аденозинового рецептора Download PDFInfo
- Publication number
- RU2340612C2 RU2340612C2 RU2005138546/04A RU2005138546A RU2340612C2 RU 2340612 C2 RU2340612 C2 RU 2340612C2 RU 2005138546/04 A RU2005138546/04 A RU 2005138546/04A RU 2005138546 A RU2005138546 A RU 2005138546A RU 2340612 C2 RU2340612 C2 RU 2340612C2
- Authority
- RU
- Russia
- Prior art keywords
- morpholin
- methoxy
- lower alkyl
- ylbenzothiazol
- imidazo
- Prior art date
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- 102000009346 Adenosine receptors Human genes 0.000 title claims 4
- 108050000203 Adenosine receptors Proteins 0.000 title claims 4
- 239000003446 ligand Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 42
- -1 2,3-dihydrobenzo[1,4]dioxin-6-yl Chemical group 0.000 claims abstract 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 21
- 239000001257 hydrogen Substances 0.000 claims abstract 21
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 9
- 150000002431 hydrogen Chemical class 0.000 claims abstract 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 7
- 150000002367 halogens Chemical class 0.000 claims abstract 6
- 125000002757 morpholinyl group Chemical group 0.000 claims abstract 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 3
- 125000001424 substituent group Chemical group 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims 18
- 239000002253 acid Substances 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 229940079593 drug Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- LOTODFAYJKCGTA-UHFFFAOYSA-N 1-[2-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl]ethanone Chemical compound C1=2SC(C=3NC=4CCN(CC=4N=3)C(C)=O)=NC=2C(OC)=CC=C1N1CCOCC1 LOTODFAYJKCGTA-UHFFFAOYSA-N 0.000 claims 1
- RKVMKTMNCRTUAN-UHFFFAOYSA-N 2-(1H-imidazol-2-yl)-4-methoxy-7-phenyl-1,3-benzothiazole Chemical compound C1=2SC(C=3NC=CN=3)=NC=2C(OC)=CC=C1C1=CC=CC=C1 RKVMKTMNCRTUAN-UHFFFAOYSA-N 0.000 claims 1
- CPZBOZXTCGQPTA-UHFFFAOYSA-N 2-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-n,n-dimethyl-1h-imidazo[4,5-b]pyridin-5-amine Chemical compound C1=2SC(C=3NC4=NC(=CC=C4N=3)N(C)C)=NC=2C(OC)=CC=C1N1CCOCC1 CPZBOZXTCGQPTA-UHFFFAOYSA-N 0.000 claims 1
- JLJXVSYDMOPZCO-UHFFFAOYSA-N 2-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-n-methyl-n-(oxan-4-ylmethyl)-1h-imidazo[4,5-b]pyridin-5-amine Chemical compound C1=2SC(C=3NC4=NC(=CC=C4N=3)N(C)CC3CCOCC3)=NC=2C(OC)=CC=C1N1CCOCC1 JLJXVSYDMOPZCO-UHFFFAOYSA-N 0.000 claims 1
- MCWZVRUTVKDXTP-UHFFFAOYSA-N 4-[2-(1,4,5,6,7,8-hexahydroimidazo[4,5-d]azepin-2-yl)-4-methoxy-1,3-benzothiazol-7-yl]morpholine;hydrochloride Chemical compound Cl.C1=2SC(C=3NC=4CCNCCC=4N=3)=NC=2C(OC)=CC=C1N1CCOCC1 MCWZVRUTVKDXTP-UHFFFAOYSA-N 0.000 claims 1
- JJMGFAPUFNRORX-UHFFFAOYSA-N 4-[2-(1H-imidazol-2-yl)-4-methoxy-1,3-benzothiazol-7-yl]morpholine Chemical compound C1=2SC(C=3NC=CN=3)=NC=2C(OC)=CC=C1N1CCOCC1 JJMGFAPUFNRORX-UHFFFAOYSA-N 0.000 claims 1
- ZWTUYJVMJRKVGS-UHFFFAOYSA-N 4-[2-(1h-benzimidazol-2-yl)-4-methoxy-1,3-benzothiazol-7-yl]morpholine Chemical compound C1=2SC(C=3NC4=CC=CC=C4N=3)=NC=2C(OC)=CC=C1N1CCOCC1 ZWTUYJVMJRKVGS-UHFFFAOYSA-N 0.000 claims 1
- DEDWAJWHTHYOPL-UHFFFAOYSA-N 4-[2-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-1h-imidazo[4,5-b]pyridin-5-yl]morpholine Chemical compound C1=2SC(C=3NC4=NC(=CC=C4N=3)N3CCOCC3)=NC=2C(OC)=CC=C1N1CCOCC1 DEDWAJWHTHYOPL-UHFFFAOYSA-N 0.000 claims 1
- XUOVAUCUYVGDJH-UHFFFAOYSA-N 4-[2-(5-chloro-1h-imidazo[4,5-b]pyridin-2-yl)-4-methoxy-1,3-benzothiazol-7-yl]morpholine Chemical compound C1=2SC(C=3NC4=NC(Cl)=CC=C4N=3)=NC=2C(OC)=CC=C1N1CCOCC1 XUOVAUCUYVGDJH-UHFFFAOYSA-N 0.000 claims 1
- QHUYXCIFGWHKFR-UHFFFAOYSA-N 4-[2-[5-(1-benzothiophen-3-yl)-1h-imidazol-2-yl]-4-methoxy-1,3-benzothiazol-7-yl]morpholine Chemical compound C1=2SC(C=3NC(=CN=3)C=3C4=CC=CC=C4SC=3)=NC=2C(OC)=CC=C1N1CCOCC1 QHUYXCIFGWHKFR-UHFFFAOYSA-N 0.000 claims 1
- VZFJOYYSZBFATF-UHFFFAOYSA-N 4-[2-[5-(2,3-dihydro-1,4-benzodioxin-6-yl)-1h-imidazol-2-yl]-4-methoxy-1,3-benzothiazol-7-yl]morpholine Chemical compound C1=2SC(C=3NC=C(N=3)C=3C=C4OCCOC4=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 VZFJOYYSZBFATF-UHFFFAOYSA-N 0.000 claims 1
- WCPASYXMFPDFMD-UHFFFAOYSA-N 4-[2-[5-chloro-3-(methoxymethyl)imidazo[4,5-b]pyridin-2-yl]-4-methoxy-1,3-benzothiazol-7-yl]morpholine Chemical compound N=1C2=CC=C(Cl)N=C2N(COC)C=1C(SC1=2)=NC1=C(OC)C=CC=2N1CCOCC1 WCPASYXMFPDFMD-UHFFFAOYSA-N 0.000 claims 1
- SDPFXDDRMKBXGN-UHFFFAOYSA-N 4-[4-methoxy-2-(4,5,6,7-tetrahydro-1h-benzimidazol-2-yl)-1,3-benzothiazol-7-yl]morpholine Chemical compound C1=2SC(C=3NC=4CCCCC=4N=3)=NC=2C(OC)=CC=C1N1CCOCC1 SDPFXDDRMKBXGN-UHFFFAOYSA-N 0.000 claims 1
- XLPWIYNXNLVLDO-UHFFFAOYSA-N 4-[4-methoxy-2-(4,5,6,7-tetrahydro-3h-imidazo[4,5-c]pyridin-2-yl)-1,3-benzothiazol-7-yl]morpholine;hydrochloride Chemical compound Cl.C1=2SC(C=3NC=4CCNCC=4N=3)=NC=2C(OC)=CC=C1N1CCOCC1 XLPWIYNXNLVLDO-UHFFFAOYSA-N 0.000 claims 1
- RYQSBPPHUGFSAI-UHFFFAOYSA-N 4-[4-methoxy-2-(5-methyl-1h-imidazo[4,5-b]pyridin-2-yl)-1,3-benzothiazol-7-yl]morpholine Chemical compound C1=2SC(C=3NC4=NC(C)=CC=C4N=3)=NC=2C(OC)=CC=C1N1CCOCC1 RYQSBPPHUGFSAI-UHFFFAOYSA-N 0.000 claims 1
- GNEQITUHPPAZOL-UHFFFAOYSA-N 4-[4-methoxy-2-(5-phenyl-1h-imidazol-2-yl)-1,3-benzothiazol-7-yl]morpholine Chemical compound C1=2SC(C=3NC=C(N=3)C=3C=CC=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 GNEQITUHPPAZOL-UHFFFAOYSA-N 0.000 claims 1
- WDKUTAMKSXNAHK-UHFFFAOYSA-N 4-[4-methoxy-2-(5-pyrrolidin-1-yl-1h-imidazo[4,5-b]pyridin-2-yl)-1,3-benzothiazol-7-yl]morpholine Chemical compound C1=2SC(C=3NC4=NC(=CC=C4N=3)N3CCCC3)=NC=2C(OC)=CC=C1N1CCOCC1 WDKUTAMKSXNAHK-UHFFFAOYSA-N 0.000 claims 1
- QWLMFYMXRDPUQE-UHFFFAOYSA-N 4-[4-methoxy-2-(5-thiophen-2-yl-1h-imidazol-2-yl)-1,3-benzothiazol-7-yl]morpholine Chemical compound C1=2SC(C=3NC=C(N=3)C=3SC=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 QWLMFYMXRDPUQE-UHFFFAOYSA-N 0.000 claims 1
- MQTWZZUUNLFRBL-UHFFFAOYSA-N 4-[4-methoxy-2-(5-thiophen-3-yl-1h-imidazol-2-yl)-1,3-benzothiazol-7-yl]morpholine Chemical compound C1=2SC(C=3NC=C(N=3)C3=CSC=C3)=NC=2C(OC)=CC=C1N1CCOCC1 MQTWZZUUNLFRBL-UHFFFAOYSA-N 0.000 claims 1
- YPRHXCJDLUXILC-UHFFFAOYSA-N 4-[4-methoxy-2-(6-methylsulfonyl-4,5,7,8-tetrahydro-1h-imidazo[4,5-d]azepin-2-yl)-1,3-benzothiazol-7-yl]morpholine Chemical compound C1=2SC(C=3NC=4CCN(CCC=4N=3)S(C)(=O)=O)=NC=2C(OC)=CC=C1N1CCOCC1 YPRHXCJDLUXILC-UHFFFAOYSA-N 0.000 claims 1
- DAMIUZUZXFWSGU-UHFFFAOYSA-N 4-[4-methoxy-2-[3-(methoxymethyl)-5-morpholin-4-ylimidazo[4,5-b]pyridin-2-yl]-1,3-benzothiazol-7-yl]morpholine Chemical compound N1=C2N(COC)C(C=3SC4=C(N5CCOCC5)C=CC(OC)=C4N=3)=NC2=CC=C1N1CCOCC1 DAMIUZUZXFWSGU-UHFFFAOYSA-N 0.000 claims 1
- FNYQSAHPJCWEOS-UHFFFAOYSA-N 4-[4-methoxy-2-[3-(methoxymethyl)-5-pyrrolidin-1-ylimidazo[4,5-b]pyridin-2-yl]-1,3-benzothiazol-7-yl]morpholine Chemical compound N1=C2N(COC)C(C=3SC4=C(N5CCOCC5)C=CC(OC)=C4N=3)=NC2=CC=C1N1CCCC1 FNYQSAHPJCWEOS-UHFFFAOYSA-N 0.000 claims 1
- LJRWVPGZPIJDRC-UHFFFAOYSA-N 4-[4-methoxy-2-[5-(thiophen-2-ylmethyl)-1h-imidazol-2-yl]-1,3-benzothiazol-7-yl]morpholine Chemical compound C1=2SC(C=3NC=C(CC=4SC=CC=4)N=3)=NC=2C(OC)=CC=C1N1CCOCC1 LJRWVPGZPIJDRC-UHFFFAOYSA-N 0.000 claims 1
- FXVJJTJYSNBBDQ-UHFFFAOYSA-N 4-[4-methoxy-2-[6-(2-methoxyethyl)-4,5,7,8-tetrahydro-1h-imidazo[4,5-d]azepin-2-yl]-1,3-benzothiazol-7-yl]morpholine Chemical compound N1C=2CCN(CCOC)CCC=2N=C1C(SC1=2)=NC1=C(OC)C=CC=2N1CCOCC1 FXVJJTJYSNBBDQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- XNARSNNGSONODU-UHFFFAOYSA-N [2-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl]-(2-methylphenyl)methanone Chemical compound C1=2SC(C=3NC=4CCN(CC=4N=3)C(=O)C=3C(=CC=CC=3)C)=NC=2C(OC)=CC=C1N1CCOCC1 XNARSNNGSONODU-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- GMKLNKFSLVGIFH-UHFFFAOYSA-N ethyl 2-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-3,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxylate Chemical compound N=1C=2CN(C(=O)OCC)CCC=2NC=1C(SC1=2)=NC1=C(OC)C=CC=2N1CCOCC1 GMKLNKFSLVGIFH-UHFFFAOYSA-N 0.000 claims 1
- ROIPASUXGYUQQN-UHFFFAOYSA-N ethyl 2-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-4,5,7,8-tetrahydro-1h-imidazo[4,5-d]azepine-6-carboxylate Chemical compound N1C=2CCN(C(=O)OCC)CCC=2N=C1C(SC1=2)=NC1=C(OC)C=CC=2N1CCOCC1 ROIPASUXGYUQQN-UHFFFAOYSA-N 0.000 claims 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- FEPLFTRQPJJCNV-UHFFFAOYSA-N tert-butyl 2-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-3,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxylate Chemical compound C1=2SC(C=3NC=4CN(CCC=4N=3)C(=O)OC(C)(C)C)=NC=2C(OC)=CC=C1N1CCOCC1 FEPLFTRQPJJCNV-UHFFFAOYSA-N 0.000 claims 1
- JITWIFDTSYODPD-UHFFFAOYSA-N tert-butyl 2-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-4,5,7,8-tetrahydro-1h-imidazo[4,5-d]azepine-6-carboxylate Chemical compound C1=2SC(C=3NC=4CCN(CCC=4N=3)C(=O)OC(C)(C)C)=NC=2C(OC)=CC=C1N1CCOCC1 JITWIFDTSYODPD-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US03009842.0 | 2003-05-13 | ||
| EP03009842 | 2003-05-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2005138546A RU2005138546A (ru) | 2006-07-27 |
| RU2340612C2 true RU2340612C2 (ru) | 2008-12-10 |
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| Application Number | Title | Priority Date | Filing Date |
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| RU2005138546/04A RU2340612C2 (ru) | 2003-05-13 | 2004-05-06 | 2-имидазобензотиазолы как лиганды аденозинового рецептора |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7122545B2 (https=) |
| EP (1) | EP1636217B1 (https=) |
| JP (1) | JP4408291B2 (https=) |
| KR (1) | KR100710453B1 (https=) |
| CN (1) | CN100372844C (https=) |
| AT (1) | ATE407133T1 (https=) |
| AU (1) | AU2004238508B2 (https=) |
| BR (1) | BRPI0410315A (https=) |
| CA (1) | CA2523959A1 (https=) |
| DE (1) | DE602004016328D1 (https=) |
| ES (1) | ES2313001T3 (https=) |
| MX (1) | MXPA05012120A (https=) |
| PL (1) | PL1636217T3 (https=) |
| RU (1) | RU2340612C2 (https=) |
| WO (1) | WO2004101558A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11453647B2 (en) | 2017-08-21 | 2022-09-27 | Merck Patent Gmbh | Benzimidazole derivatives as adenosine receptor antagonists |
| RU2781429C2 (ru) * | 2017-08-21 | 2022-10-11 | Мерк Патент Гмбх | Бензимидазольные производные в качестве антагонистов аденозиновых рецепторов |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1910384T3 (da) * | 2005-08-04 | 2012-12-17 | Sirtris Pharmaceuticals Inc | Imidazo [2,1-b] thiazol-derivater som sirtuinmodulerende forbindelser |
| TW201018678A (en) | 2006-01-27 | 2010-05-16 | Astrazeneca Ab | Novel heteroaryl substituted benzothiazoles |
| TW200813035A (en) | 2006-06-19 | 2008-03-16 | Astrazeneca Ab | Novel heteroaryl substituted benzoxazoles |
| TW200901998A (en) | 2007-03-06 | 2009-01-16 | Astrazeneca Ab | Novel 2-heteroaryl substituted benzothiophenes and benzofuranes |
| MY159575A (en) * | 2009-04-02 | 2017-01-13 | Merck Serono Sa | Dihydroorotate dehydrogenase inhibitors |
| WO2010114971A1 (en) * | 2009-04-03 | 2010-10-07 | Sepracor Inc. | Compounds for treating disorders mediated by metabotropic glutamate receptor 5, and methods of use thereof |
| US8575336B2 (en) | 2011-07-27 | 2013-11-05 | Pfizer Limited | Indazoles |
| WO2016164565A1 (en) * | 2015-04-08 | 2016-10-13 | University Of Delaware | Trans-cycloheptenes and hetero-trans-cycloheptenes for bioorthogonal coupling |
| WO2018193090A2 (en) * | 2017-04-21 | 2018-10-25 | Amneal Pharmaceuticals Company Gmbh | Process for preparation of eliglustat hemitartrate and intermediates thereof |
| WO2025160629A1 (en) * | 2024-01-31 | 2025-08-07 | Certa Therapeutics Pty Ltd | Proton sensing gpcr modulators |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0295656A1 (en) * | 1987-06-17 | 1988-12-21 | Eisai Co., Ltd. | Benzothiazole derivative, its use, and pharmaceutical compositions comprising it |
| SU1681728A3 (ru) * | 1988-05-24 | 1991-09-30 | Пфайзер Инк. (Фирма) | Способ получени производных N-(бензтиазолил-2)амидов бензойной или тиазол-4-карбоновой кислоты |
| US6521754B2 (en) * | 2000-06-21 | 2003-02-18 | Hoffman-La Roche Inc. | Benzothiazole derivatives with activity as adenosine receptor ligands |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1260444B (it) * | 1992-01-24 | 1996-04-09 | Mario Brufani | Derivati della 8-(1-amminocicloalchil)1,3-dialchilxantina, procedimenbto di preparazione e loro composizioni farmaceutiche antidepressive, nootropiche e psicostimolanti |
| US6037473A (en) * | 1997-11-13 | 2000-03-14 | Haarmann & Reimer Gmbh | Use of substituted benzazoles as UV absorbers, new benzazoles and processes for their preparation |
| US6841549B1 (en) * | 1999-07-02 | 2005-01-11 | Eisai Co., Ltd. | Condensed imidazole compounds and a therapeutic agent for diabetes mellitus |
| MXPA05012369A (es) * | 2003-05-21 | 2006-02-02 | Hoffmann La Roche | Derivados de benzotiazol y uso de los mismos en el tratamiento de enfermedades relacionadas con el receptor a2a de adenosina. |
-
2004
- 2004-05-06 KR KR1020057021535A patent/KR100710453B1/ko not_active Expired - Fee Related
- 2004-05-06 MX MXPA05012120A patent/MXPA05012120A/es active IP Right Grant
- 2004-05-06 PL PL04731369T patent/PL1636217T3/pl unknown
- 2004-05-06 WO PCT/EP2004/004843 patent/WO2004101558A1/en not_active Ceased
- 2004-05-06 CA CA002523959A patent/CA2523959A1/en not_active Abandoned
- 2004-05-06 CN CNB2004800117819A patent/CN100372844C/zh not_active Expired - Fee Related
- 2004-05-06 AT AT04731369T patent/ATE407133T1/de not_active IP Right Cessation
- 2004-05-06 BR BRPI0410315-7A patent/BRPI0410315A/pt not_active IP Right Cessation
- 2004-05-06 AU AU2004238508A patent/AU2004238508B2/en not_active Ceased
- 2004-05-06 RU RU2005138546/04A patent/RU2340612C2/ru not_active IP Right Cessation
- 2004-05-06 JP JP2006529752A patent/JP4408291B2/ja not_active Expired - Fee Related
- 2004-05-06 DE DE602004016328T patent/DE602004016328D1/de not_active Expired - Lifetime
- 2004-05-06 ES ES04731369T patent/ES2313001T3/es not_active Expired - Lifetime
- 2004-05-06 EP EP04731369A patent/EP1636217B1/en not_active Expired - Lifetime
- 2004-05-11 US US10/843,241 patent/US7122545B2/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0295656A1 (en) * | 1987-06-17 | 1988-12-21 | Eisai Co., Ltd. | Benzothiazole derivative, its use, and pharmaceutical compositions comprising it |
| SU1681728A3 (ru) * | 1988-05-24 | 1991-09-30 | Пфайзер Инк. (Фирма) | Способ получени производных N-(бензтиазолил-2)амидов бензойной или тиазол-4-карбоновой кислоты |
| US6521754B2 (en) * | 2000-06-21 | 2003-02-18 | Hoffman-La Roche Inc. | Benzothiazole derivatives with activity as adenosine receptor ligands |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11453647B2 (en) | 2017-08-21 | 2022-09-27 | Merck Patent Gmbh | Benzimidazole derivatives as adenosine receptor antagonists |
| RU2781429C2 (ru) * | 2017-08-21 | 2022-10-11 | Мерк Патент Гмбх | Бензимидазольные производные в качестве антагонистов аденозиновых рецепторов |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100372844C (zh) | 2008-03-05 |
| ES2313001T3 (es) | 2009-03-01 |
| ATE407133T1 (de) | 2008-09-15 |
| RU2005138546A (ru) | 2006-07-27 |
| JP4408291B2 (ja) | 2010-02-03 |
| BRPI0410315A (pt) | 2006-05-23 |
| US7122545B2 (en) | 2006-10-17 |
| CN1780831A (zh) | 2006-05-31 |
| KR100710453B1 (ko) | 2007-04-24 |
| KR20060009928A (ko) | 2006-02-01 |
| AU2004238508B2 (en) | 2009-11-19 |
| PL1636217T3 (pl) | 2009-02-27 |
| DE602004016328D1 (de) | 2008-10-16 |
| US20040229862A1 (en) | 2004-11-18 |
| JP2006528215A (ja) | 2006-12-14 |
| CA2523959A1 (en) | 2004-11-25 |
| EP1636217A1 (en) | 2006-03-22 |
| WO2004101558A1 (en) | 2004-11-25 |
| AU2004238508A1 (en) | 2004-11-25 |
| MXPA05012120A (es) | 2006-02-08 |
| EP1636217B1 (en) | 2008-09-03 |
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| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20110507 |