RU2010123778A - Процесс - Google Patents
Процесс Download PDFInfo
- Publication number
- RU2010123778A RU2010123778A RU2010123778/04A RU2010123778A RU2010123778A RU 2010123778 A RU2010123778 A RU 2010123778A RU 2010123778/04 A RU2010123778/04 A RU 2010123778/04A RU 2010123778 A RU2010123778 A RU 2010123778A RU 2010123778 A RU2010123778 A RU 2010123778A
- Authority
- RU
- Russia
- Prior art keywords
- formula
- compound
- process according
- thion
- dihydroimidazol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 44
- 150000001875 compounds Chemical class 0.000 claims abstract 43
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract 12
- 125000005843 halogen group Chemical group 0.000 claims abstract 12
- 125000003118 aryl group Chemical group 0.000 claims abstract 10
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 claims abstract 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 4
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 4
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 4
- 238000006243 chemical reaction Methods 0.000 claims abstract 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 4
- 239000011737 fluorine Substances 0.000 claims abstract 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 4
- 150000002367 halogens Chemical class 0.000 claims abstract 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 4
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 4
- 230000009466 transformation Effects 0.000 claims abstract 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 3
- 230000008707 rearrangement Effects 0.000 claims abstract 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000006969 Curtius rearrangement reaction Methods 0.000 claims abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052794 bromium Inorganic materials 0.000 claims abstract 2
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 2
- 239000000460 chlorine Substances 0.000 claims abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 2
- 229910052740 iodine Inorganic materials 0.000 claims abstract 2
- 239000011630 iodine Substances 0.000 claims abstract 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 3
- CWWWTTYMUOYSQA-LLVKDONJSA-N 4-(2-aminoethyl)-3-[(3r)-6,8-difluoro-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound NCCC1=CNC(=S)N1[C@@H]1CC2=CC(F)=CC(F)=C2OC1 CWWWTTYMUOYSQA-LLVKDONJSA-N 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000002346 iodo group Chemical group I* 0.000 claims 2
- 230000001681 protective effect Effects 0.000 claims 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
- CIZSXHJFJOUTBA-CYBMUJFWSA-N 3-[(3r)-3,4-dihydro-2h-chromen-3-yl]-4-[2-(methylamino)ethyl]-1h-imidazole-2-thione Chemical compound CNCCC1=CNC(=S)N1[C@@H]1CC2=CC=CC=C2OC1 CIZSXHJFJOUTBA-CYBMUJFWSA-N 0.000 claims 1
- GFTROSXKPGWDQY-GFCCVEGCSA-N 3-[(3r)-6,8-difluoro-3,4-dihydro-2h-chromen-3-yl]-4-[2-(methylamino)ethyl]-1h-imidazole-2-thione Chemical compound CNCCC1=CNC(=S)N1[C@@H]1CC2=CC(F)=CC(F)=C2OC1 GFTROSXKPGWDQY-GFCCVEGCSA-N 0.000 claims 1
- FDILNPIPLDMEKH-GFCCVEGCSA-N 3-[(3r)-6-hydroxy-3,4-dihydro-2h-chromen-3-yl]-4-[2-(methylamino)ethyl]-1h-imidazole-2-thione Chemical compound CNCCC1=CNC(=S)N1[C@@H]1CC2=CC(O)=CC=C2OC1 FDILNPIPLDMEKH-GFCCVEGCSA-N 0.000 claims 1
- VHYPBFDDZNKESQ-GFCCVEGCSA-N 4-(2-aminoethyl)-3-[(3r)-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound NCCC1=CNC(=S)N1[C@@H]1CC2=CC=CC=C2OC1 VHYPBFDDZNKESQ-GFCCVEGCSA-N 0.000 claims 1
- JBMQYQOWXZAPDM-SECBINFHSA-N 4-(2-aminoethyl)-3-[(3r)-6,7,8-trifluoro-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound NCCC1=CNC(=S)N1[C@@H]1CC(C=C(F)C(F)=C2F)=C2OC1 JBMQYQOWXZAPDM-SECBINFHSA-N 0.000 claims 1
- DZRNOQCTKOBUAK-SNVBAGLBSA-N 4-(2-aminoethyl)-3-[(3r)-6,7-difluoro-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound NCCC1=CNC(=S)N1[C@@H]1CC2=CC(F)=C(F)C=C2OC1 DZRNOQCTKOBUAK-SNVBAGLBSA-N 0.000 claims 1
- IACPBROODVYPRT-GFCCVEGCSA-N 4-(2-aminoethyl)-3-[(3r)-6-chloro-8-methoxy-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound N1([C@@H]2CC=3C=C(Cl)C=C(C=3OC2)OC)C(CCN)=CNC1=S IACPBROODVYPRT-GFCCVEGCSA-N 0.000 claims 1
- ZVNPVFPANOYSGK-GFCCVEGCSA-N 4-(2-aminoethyl)-3-[(3r)-6-fluoro-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound NCCC1=CNC(=S)N1[C@@H]1CC2=CC(F)=CC=C2OC1 ZVNPVFPANOYSGK-GFCCVEGCSA-N 0.000 claims 1
- LYOMOBDZZKIPDC-LLVKDONJSA-N 4-(2-aminoethyl)-3-[(3r)-6-hydroxy-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound NCCC1=CNC(=S)N1[C@@H]1CC2=CC(O)=CC=C2OC1 LYOMOBDZZKIPDC-LLVKDONJSA-N 0.000 claims 1
- RUDRRZIQZRQSRL-GFCCVEGCSA-N 4-(2-aminoethyl)-3-[(3r)-6-methoxy-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound N1([C@H]2COC3=CC=C(C=C3C2)OC)C(CCN)=CNC1=S RUDRRZIQZRQSRL-GFCCVEGCSA-N 0.000 claims 1
- RWBYHVOPHRDVAI-GFCCVEGCSA-N 4-(2-aminoethyl)-3-[(3r)-6-nitro-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound NCCC1=CNC(=S)N1[C@@H]1CC2=CC([N+]([O-])=O)=CC=C2OC1 RWBYHVOPHRDVAI-GFCCVEGCSA-N 0.000 claims 1
- GYMJLUMPHLFEKV-GOSISDBHSA-N 4-(2-aminoethyl)-3-[(3r)-7-benzyl-6-hydroxy-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound NCCC1=CNC(=S)N1[C@@H]1CC2=CC(O)=C(CC=3C=CC=CC=3)C=C2OC1 GYMJLUMPHLFEKV-GOSISDBHSA-N 0.000 claims 1
- ZLRRWMLDYDBHEB-LLVKDONJSA-N 4-(2-aminoethyl)-3-[(3r)-8-chloro-6-methoxy-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound N1([C@H]2COC3=C(Cl)C=C(C=C3C2)OC)C(CCN)=CNC1=S ZLRRWMLDYDBHEB-LLVKDONJSA-N 0.000 claims 1
- XRNOJLDIRCCQPD-LLVKDONJSA-N 4-(2-aminoethyl)-3-[(3r)-8-fluoro-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound NCCC1=CNC(=S)N1[C@@H]1CC2=CC=CC(F)=C2OC1 XRNOJLDIRCCQPD-LLVKDONJSA-N 0.000 claims 1
- TXJFZUNUABXLTG-LLVKDONJSA-N 4-(2-aminoethyl)-3-[(3r)-8-hydroxy-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound NCCC1=CNC(=S)N1[C@@H]1CC2=CC=CC(O)=C2OC1 TXJFZUNUABXLTG-LLVKDONJSA-N 0.000 claims 1
- MIUACEHSFFFAPE-GFCCVEGCSA-N 4-(2-aminoethyl)-3-[(3r)-8-methoxy-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound N1([C@@H]2CC=3C=CC=C(C=3OC2)OC)C(CCN)=CNC1=S MIUACEHSFFFAPE-GFCCVEGCSA-N 0.000 claims 1
- FNPSIDQPVWLMAI-LLVKDONJSA-N 4-(2-aminoethyl)-3-[(3r)-8-nitro-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound NCCC1=CNC(=S)N1[C@@H]1CC(C=CC=C2[N+]([O-])=O)=C2OC1 FNPSIDQPVWLMAI-LLVKDONJSA-N 0.000 claims 1
- OQDLAKHVUUXKNL-SNVBAGLBSA-N 4-(aminomethyl)-3-[(3r)-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound NCC1=CNC(=S)N1[C@@H]1CC2=CC=CC=C2OC1 OQDLAKHVUUXKNL-SNVBAGLBSA-N 0.000 claims 1
- GHNQCWKGQHAFDS-SECBINFHSA-N 4-(aminomethyl)-3-[(3r)-6,8-difluoro-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound NCC1=CNC(=S)N1[C@@H]1CC2=CC(F)=CC(F)=C2OC1 GHNQCWKGQHAFDS-SECBINFHSA-N 0.000 claims 1
- XIDMCXLNSQNAPP-SECBINFHSA-N 4-(aminomethyl)-3-[(3r)-6-hydroxy-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound NCC1=CNC(=S)N1[C@@H]1CC2=CC(O)=CC=C2OC1 XIDMCXLNSQNAPP-SECBINFHSA-N 0.000 claims 1
- INYLGVJSDTUSNC-GOSISDBHSA-N 4-[2-(benzylamino)ethyl]-3-[(3r)-6-hydroxy-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound C=1NC(=S)N([C@H]2COC3=CC=C(C=C3C2)O)C=1CCNCC1=CC=CC=C1 INYLGVJSDTUSNC-GOSISDBHSA-N 0.000 claims 1
- AMHOPCZYGXZAKW-LJQANCHMSA-N 4-[2-(benzylamino)ethyl]-3-[(3r)-6-methoxy-3,4-dihydro-2h-chromen-3-yl]-1h-imidazole-2-thione Chemical compound C=1NC(=S)N([C@H]2COC3=CC=C(C=C3C2)OC)C=1CCNCC1=CC=CC=C1 AMHOPCZYGXZAKW-LJQANCHMSA-N 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- 229940126062 Compound A Drugs 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- SIHRNZKSJPIRJH-CQSZACIVSA-N n-[(3r)-3-[4-(2-aminoethyl)-2-sulfanylidene-1h-imidazol-3-yl]-3,4-dihydro-2h-chromen-6-yl]acetamide Chemical compound N1([C@H]2COC3=CC=C(C=C3C2)NC(=O)C)C(CCN)=CNC1=S SIHRNZKSJPIRJH-CQSZACIVSA-N 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 125000005544 phthalimido group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US98746707P | 2007-11-13 | 2007-11-13 | |
| US60/987,467 | 2007-11-13 | ||
| US8592708P | 2008-08-04 | 2008-08-04 | |
| US61/085,927 | 2008-08-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2010123778A true RU2010123778A (ru) | 2011-12-20 |
Family
ID=40550012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2010123778/04A RU2010123778A (ru) | 2007-11-13 | 2008-11-13 | Процесс |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20100298580A1 (enExample) |
| EP (1) | EP2217585A2 (enExample) |
| JP (1) | JP2011503175A (enExample) |
| KR (1) | KR20100102606A (enExample) |
| CN (1) | CN101952271A (enExample) |
| AR (1) | AR069311A1 (enExample) |
| AU (1) | AU2008321625A1 (enExample) |
| BR (1) | BRPI0818105A2 (enExample) |
| CA (1) | CA2705512A1 (enExample) |
| MX (1) | MX2010005193A (enExample) |
| RU (1) | RU2010123778A (enExample) |
| TW (1) | TW200927740A (enExample) |
| WO (1) | WO2009064210A2 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201316410D0 (en) | 2013-09-13 | 2013-10-30 | Bial Portela & Ca Sa | Processes for preparing peripherally-selective inhibitors of dopamine-?-hydroxylase and intermediates for use therein |
| US11875700B2 (en) | 2014-05-20 | 2024-01-16 | Jessica Robinson | Systems and methods for providing communication services |
| CN110590728B (zh) * | 2019-10-15 | 2022-03-22 | 青岛科技大学 | 一种多取代4-苯基色满类化合物的合成方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0232279B2 (ja) * | 1982-08-12 | 1990-07-19 | Kowa Co | Jihidorobenzopiranjioorunoseiho |
| SE8605504D0 (sv) * | 1986-12-19 | 1986-12-19 | Astra Laekemedel Ab | Novel chroman derivatives |
| EP0757677B1 (en) * | 1994-04-26 | 2003-06-18 | Syntex (U.S.A.) LLC | Benzocyclohexylimidazolethione derivatives |
| US6867224B2 (en) * | 2002-03-07 | 2005-03-15 | Warner-Lambert Company | Compounds that modulate PPAR activity and methods of preparation |
| JP2004075614A (ja) * | 2002-08-20 | 2004-03-11 | Sankyo Co Ltd | クロメン誘導体を含有する医薬 |
| US7125904B2 (en) * | 2002-10-11 | 2006-10-24 | Portela & C.A., S.A. | Peripherally-selective inhibitors of dopamine-β-hydroxylase and method of their preparation |
| US20050032873A1 (en) * | 2003-07-30 | 2005-02-10 | Wyeth | 3-Amino chroman and 2-amino tetralin derivatives |
| US20050245489A1 (en) * | 2004-05-03 | 2005-11-03 | Pinney Kevin G | Chromene-containing compounds with anti-tubulin and vascular targeting activity |
| US7456214B2 (en) * | 2004-05-03 | 2008-11-25 | Baylor University | Chromene-containing compounds with anti-tubulin and vascular targeting activity |
| NZ552173A (en) * | 2004-06-25 | 2010-07-30 | Janssen Pharmaceutica Nv | Quaternary salt CCR2 antagonists |
| CN101068801B (zh) * | 2004-10-14 | 2012-11-14 | 艾博特股份有限两合公司 | 适用于治疗对于多巴胺d3受体的调节有反应的疾病的芳基磺酰基甲基或芳基磺酰胺取代的芳族化合物 |
| CN101365682A (zh) * | 2005-12-08 | 2009-02-11 | 千禧药品公司 | 具有激酶抑制活性的双环化合物 |
| AR064308A1 (es) * | 2006-12-12 | 2009-03-25 | Portela & Ca Sa | Proceso de obtencion de cromanos, los mencionados compuestos, un intermediario para su sintesis, un metodo de sintesis de croman-3-il-dihidroimidazol-2-tiona que los emplea, un complejo de metales de transicion derivado de fosfin-bipiridina y su uso como catalizador. |
-
2008
- 2008-11-12 TW TW097143774A patent/TW200927740A/zh unknown
- 2008-11-13 US US12/742,738 patent/US20100298580A1/en not_active Abandoned
- 2008-11-13 CA CA2705512A patent/CA2705512A1/en not_active Abandoned
- 2008-11-13 JP JP2010533987A patent/JP2011503175A/ja active Pending
- 2008-11-13 MX MX2010005193A patent/MX2010005193A/es not_active Application Discontinuation
- 2008-11-13 EP EP08850447A patent/EP2217585A2/en not_active Withdrawn
- 2008-11-13 KR KR1020107012805A patent/KR20100102606A/ko not_active Withdrawn
- 2008-11-13 RU RU2010123778/04A patent/RU2010123778A/ru unknown
- 2008-11-13 BR BRPI0818105A patent/BRPI0818105A2/pt not_active IP Right Cessation
- 2008-11-13 AR ARP080104958A patent/AR069311A1/es unknown
- 2008-11-13 CN CN2008801246552A patent/CN101952271A/zh active Pending
- 2008-11-13 WO PCT/PT2008/000048 patent/WO2009064210A2/en not_active Ceased
- 2008-11-13 AU AU2008321625A patent/AU2008321625A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| TW200927740A (en) | 2009-07-01 |
| WO2009064210A3 (en) | 2009-12-30 |
| CN101952271A (zh) | 2011-01-19 |
| CA2705512A1 (en) | 2009-05-22 |
| BRPI0818105A2 (pt) | 2019-09-24 |
| KR20100102606A (ko) | 2010-09-24 |
| EP2217585A2 (en) | 2010-08-18 |
| JP2011503175A (ja) | 2011-01-27 |
| AU2008321625A1 (en) | 2009-05-22 |
| WO2009064210A2 (en) | 2009-05-22 |
| US20100298580A1 (en) | 2010-11-25 |
| AR069311A1 (es) | 2010-01-13 |
| MX2010005193A (es) | 2010-06-02 |
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