ZA200209067B - Method for producing benzo annelated heterocycles. - Google Patents
Method for producing benzo annelated heterocycles. Download PDFInfo
- Publication number
- ZA200209067B ZA200209067B ZA200209067A ZA200209067A ZA200209067B ZA 200209067 B ZA200209067 B ZA 200209067B ZA 200209067 A ZA200209067 A ZA 200209067A ZA 200209067 A ZA200209067 A ZA 200209067A ZA 200209067 B ZA200209067 B ZA 200209067B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- carboxylate
- thieno
- benzo
- chloro
- Prior art date
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- 125000000623 heterocyclic group Chemical group 0.000 title claims description 15
- 125000005605 benzo group Chemical group 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title description 4
- 238000000034 method Methods 0.000 claims description 32
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 30
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 25
- -1 alkyl 2-acetylaminotetrahydrobenzo- thiophene-3-carboxylate Chemical compound 0.000 claims description 25
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 229910000510 noble metal Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 claims description 13
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 10
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 230000003197 catalytic effect Effects 0.000 claims description 9
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- 238000005947 deacylation reaction Methods 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 238000003786 synthesis reaction Methods 0.000 claims description 9
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
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- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
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- 238000009835 boiling Methods 0.000 claims description 7
- XNASJEQIJMDBQN-UHFFFAOYSA-N ethyl 2-amino-1-benzothiophene-3-carboxylate Chemical compound C1=CC=C2C(C(=O)OCC)=C(N)SC2=C1 XNASJEQIJMDBQN-UHFFFAOYSA-N 0.000 claims description 7
- 239000012320 chlorinating reagent Substances 0.000 claims description 6
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
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- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 4
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 claims description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000001851 cinnamic acid derivatives Chemical class 0.000 claims description 4
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- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 4
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 4
- 235000021286 stilbenes Nutrition 0.000 claims description 4
- 229910000018 strontium carbonate Inorganic materials 0.000 claims description 4
- 150000001608 tolans Chemical class 0.000 claims description 4
- OCNMSDZALRAYEX-UHFFFAOYSA-N (3-chloro-4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1Cl OCNMSDZALRAYEX-UHFFFAOYSA-N 0.000 claims description 3
- WZNYBICPLIMKNV-UHFFFAOYSA-N 4-(aminomethyl)-2-chlorophenol Chemical compound NCC1=CC=C(O)C(Cl)=C1 WZNYBICPLIMKNV-UHFFFAOYSA-N 0.000 claims description 3
- 229910002090 carbon oxide Inorganic materials 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- KJJPAVCZQWWWMM-UHFFFAOYSA-N 4-[4-[(3-chloro-4-methoxyphenyl)methylamino]-[1]benzothiolo[2,3-d]pyrimidin-2-yl]cyclohexane-1-carboxylic acid Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NC(C2CCC(CC2)C(O)=O)=NC2=C1C1=CC=CC=C1S2 KJJPAVCZQWWWMM-UHFFFAOYSA-N 0.000 claims 2
- YNVOMSDITJMNET-UHFFFAOYSA-M thiophene-3-carboxylate Chemical compound [O-]C(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-M 0.000 claims 2
- GOWMBYUZXIZENX-CAUSLRQDSA-N 1-[(2r,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(hexadecylamino)pyrimidin-2-one Chemical compound O=C1N=C(NCCCCCCCCCCCCCCCC)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 GOWMBYUZXIZENX-CAUSLRQDSA-N 0.000 claims 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 15
- 239000000370 acceptor Substances 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006356 dehydrogenation reaction Methods 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
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- 238000005899 aromatization reaction Methods 0.000 description 5
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 5
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- VCKZNVMJHXMZED-UHFFFAOYSA-N methyl 4-(4-chloro-[1]benzothiolo[2,3-d]pyrimidin-2-yl)cyclohexane-1-carboxylate Chemical compound C1CC(C(=O)OC)CCC1C1=NC(Cl)=C2C3=CC=CC=C3SC2=N1 VCKZNVMJHXMZED-UHFFFAOYSA-N 0.000 description 3
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- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 2
- RTAIQZZASOBMQE-UHFFFAOYSA-N 4-[4-[(3-chloro-4-hydroxyphenyl)methylamino]-[1]benzothiolo[2,3-d]pyrimidin-2-yl]cyclohexane-1-carboxylic acid Chemical compound C1CC(C(=O)O)CCC1C1=NC(NCC=2C=C(Cl)C(O)=CC=2)=C2C3=CC=CC=C3SC2=N1 RTAIQZZASOBMQE-UHFFFAOYSA-N 0.000 description 2
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
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- HUQQDOKKXZCNOI-UHFFFAOYSA-N methyl 2-amino-1-benzothiophene-3-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=C(N)SC2=C1 HUQQDOKKXZCNOI-UHFFFAOYSA-N 0.000 description 2
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- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- KELIOZMTDOSCMM-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1-benzothiophene Chemical group C1C=CC=C2SCCC21 KELIOZMTDOSCMM-UHFFFAOYSA-N 0.000 description 1
- KFVFYVHYWICGOY-UHFFFAOYSA-N 2-amino-1-benzothiophene-3-carboxylic acid Chemical compound C1=CC=C2C(C(O)=O)=C(N)SC2=C1 KFVFYVHYWICGOY-UHFFFAOYSA-N 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- ZTZZYHDCSGUPSH-UHFFFAOYSA-N methyl 2-acetamido-1-benzothiophene-3-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=C(NC(C)=O)SC2=C1 ZTZZYHDCSGUPSH-UHFFFAOYSA-N 0.000 description 1
- NLSSEISPKNBAGM-UHFFFAOYSA-N methyl 2-acetamido-2,3,3a,4-tetrahydro-1-benzothiophene-3-carboxylate Chemical compound C1=CCC2C(C(=O)OC)C(NC(C)=O)SC2=C1 NLSSEISPKNBAGM-UHFFFAOYSA-N 0.000 description 1
- XBXSJPMEVLEUMB-UHFFFAOYSA-N methyl 3-cyanocyclohexane-1-carboxylate Chemical compound COC(=O)C1CCCC(C#N)C1 XBXSJPMEVLEUMB-UHFFFAOYSA-N 0.000 description 1
- IZOYNSYJTKFQJJ-UHFFFAOYSA-N methyl 4-(4-oxo-3h-[1]benzothiolo[2,3-d]pyrimidin-2-yl)cyclohexane-1-carboxylate Chemical compound C1CC(C(=O)OC)CCC1C1=NC(O)=C2C3=CC=CC=C3SC2=N1 IZOYNSYJTKFQJJ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- INIOZDBICVTGEO-UHFFFAOYSA-L palladium(ii) bromide Chemical compound Br[Pd]Br INIOZDBICVTGEO-UHFFFAOYSA-L 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 239000002590 phosphodiesterase V inhibitor Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10017947A DE10017947A1 (de) | 2000-04-11 | 2000-04-11 | Verfahren zur Herstellung benzo-annelierter Heterocyclen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200209067B true ZA200209067B (en) | 2004-01-21 |
Family
ID=7638339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200209067A ZA200209067B (en) | 2000-04-11 | 2002-11-07 | Method for producing benzo annelated heterocycles. |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6723848B2 (es) |
| EP (1) | EP1280792B1 (es) |
| JP (1) | JP2003530392A (es) |
| KR (1) | KR20030005273A (es) |
| CN (2) | CN1214023C (es) |
| AR (1) | AR028328A1 (es) |
| AT (1) | ATE271046T1 (es) |
| AU (2) | AU2001248340B2 (es) |
| BR (1) | BR0109937A (es) |
| CA (1) | CA2405720A1 (es) |
| DE (2) | DE10017947A1 (es) |
| ES (1) | ES2225513T3 (es) |
| HU (1) | HUP0300609A2 (es) |
| MX (1) | MXPA02009968A (es) |
| NO (1) | NO20024887L (es) |
| PL (1) | PL356558A1 (es) |
| PT (1) | PT1280792E (es) |
| RU (1) | RU2260004C2 (es) |
| SK (1) | SK13452002A3 (es) |
| TR (1) | TR200402271T4 (es) |
| WO (1) | WO2001077099A1 (es) |
| ZA (1) | ZA200209067B (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7115436B2 (en) * | 2004-02-12 | 2006-10-03 | Robert Bosch Gmbh | Integrated getter area for wafer level encapsulated microelectromechanical systems |
| ATE555091T1 (de) | 2006-02-03 | 2012-05-15 | Bionomics Ltd | Substituierte benzofurane, benzothiophene, benzoselenophene und indole und ihre verwendung als tubulinpolymerisationsinhibitoren |
| US20110015239A1 (en) * | 2007-12-14 | 2011-01-20 | The Regents Of The University Of California | Inhibitors of calcium-activated chloride channels |
| CN102093334B (zh) * | 2011-02-22 | 2013-05-08 | 郑州大学 | 一组稠环噻吩类化合物的合成方法 |
| KR102117083B1 (ko) | 2018-10-30 | 2020-05-29 | 계명대학교 산학협력단 | 벤조헤테로사이클 화합물 및 이를 유효성분으로 함유하는 암질환 예방 또는 치료용 조성물 |
| RU2722595C1 (ru) * | 2019-12-27 | 2020-06-02 | Федеральное государственное бюджетное учреждение науки институт биоорганической химии им. академиков М.М. Шемякина и Ю.А. Овчинникова Российской академии наук (ИБХ РАН) | Способ получения сложного эфира 4-формил-6,7-дигидрокси-бензо[b]тиофен-3-карбоновой кислоты |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3637223A1 (de) * | 1986-11-03 | 1988-05-05 | Bayer Ag | Verfahren zur herstellung von thiophenverbindungen |
| GB9301192D0 (en) * | 1993-06-09 | 1993-06-09 | Trott Francis W | Flower shaped mechanised table |
| US5869486A (en) * | 1995-02-24 | 1999-02-09 | Ono Pharmaceutical Co., Ltd. | Fused pyrimidines and pyriazines as pharmaceutical compounds |
| DE19819023A1 (de) | 1998-04-29 | 1999-11-04 | Merck Patent Gmbh | Thienopyrimidine |
| DE19928146A1 (de) * | 1999-06-19 | 2000-12-21 | Merck Patent Gmbh | Thienopyrimidine |
-
2000
- 2000-04-11 DE DE10017947A patent/DE10017947A1/de not_active Withdrawn
-
2001
- 2001-03-09 RU RU2002129560/04A patent/RU2260004C2/ru not_active IP Right Cessation
- 2001-03-09 AT AT01921324T patent/ATE271046T1/de not_active IP Right Cessation
- 2001-03-09 CA CA002405720A patent/CA2405720A1/en not_active Abandoned
- 2001-03-09 JP JP2001575572A patent/JP2003530392A/ja active Pending
- 2001-03-09 BR BR0109937-0A patent/BR0109937A/pt not_active IP Right Cessation
- 2001-03-09 DE DE50102855T patent/DE50102855D1/de not_active Expired - Fee Related
- 2001-03-09 SK SK1345-2002A patent/SK13452002A3/sk unknown
- 2001-03-09 EP EP01921324A patent/EP1280792B1/de not_active Expired - Lifetime
- 2001-03-09 HU HU0300609A patent/HUP0300609A2/hu unknown
- 2001-03-09 PT PT01921324T patent/PT1280792E/pt unknown
- 2001-03-09 PL PL01356558A patent/PL356558A1/xx unknown
- 2001-03-09 CN CNB018078818A patent/CN1214023C/zh not_active Expired - Fee Related
- 2001-03-09 ES ES01921324T patent/ES2225513T3/es not_active Expired - Lifetime
- 2001-03-09 KR KR1020027013539A patent/KR20030005273A/ko not_active Application Discontinuation
- 2001-03-09 WO PCT/EP2001/002672 patent/WO2001077099A1/de not_active Application Discontinuation
- 2001-03-09 AU AU2001248340A patent/AU2001248340B2/en not_active Ceased
- 2001-03-09 TR TR2004/02271T patent/TR200402271T4/xx unknown
- 2001-03-09 CN CNA2004100879829A patent/CN1636998A/zh active Pending
- 2001-03-09 MX MXPA02009968A patent/MXPA02009968A/es not_active Application Discontinuation
- 2001-03-09 AU AU4834001A patent/AU4834001A/xx active Pending
- 2001-03-09 US US10/257,139 patent/US6723848B2/en not_active Expired - Fee Related
- 2001-04-11 AR ARP010101729A patent/AR028328A1/es unknown
-
2002
- 2002-10-10 NO NO20024887A patent/NO20024887L/no not_active Application Discontinuation
- 2002-11-07 ZA ZA200209067A patent/ZA200209067B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO20024887D0 (no) | 2002-10-10 |
| US6723848B2 (en) | 2004-04-20 |
| ATE271046T1 (de) | 2004-07-15 |
| AU4834001A (en) | 2001-10-23 |
| EP1280792A1 (de) | 2003-02-05 |
| ES2225513T3 (es) | 2005-03-16 |
| JP2003530392A (ja) | 2003-10-14 |
| CN1636998A (zh) | 2005-07-13 |
| BR0109937A (pt) | 2003-05-27 |
| AU2001248340B2 (en) | 2005-09-22 |
| US20030078422A1 (en) | 2003-04-24 |
| RU2260004C2 (ru) | 2005-09-10 |
| PT1280792E (pt) | 2004-11-30 |
| MXPA02009968A (es) | 2003-03-10 |
| SK13452002A3 (sk) | 2003-03-04 |
| DE10017947A1 (de) | 2001-10-25 |
| DE50102855D1 (de) | 2004-08-19 |
| WO2001077099A1 (de) | 2001-10-18 |
| CA2405720A1 (en) | 2001-10-18 |
| CN1214023C (zh) | 2005-08-10 |
| TR200402271T4 (tr) | 2004-12-21 |
| CN1422265A (zh) | 2003-06-04 |
| PL356558A1 (en) | 2004-06-28 |
| KR20030005273A (ko) | 2003-01-17 |
| EP1280792B1 (de) | 2004-07-14 |
| NO20024887L (no) | 2002-10-10 |
| AR028328A1 (es) | 2003-05-07 |
| HUP0300609A2 (hu) | 2003-07-28 |
| RU2002129560A (ru) | 2004-03-27 |
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