UA79655C2 - Process for the preparation of imidazolyl compounds - Google Patents
Process for the preparation of imidazolyl compounds Download PDFInfo
- Publication number
- UA79655C2 UA79655C2 UAA200505941A UA2005005941A UA79655C2 UA 79655 C2 UA79655 C2 UA 79655C2 UA A200505941 A UAA200505941 A UA A200505941A UA 2005005941 A UA2005005941 A UA 2005005941A UA 79655 C2 UA79655 C2 UA 79655C2
- Authority
- UA
- Ukraine
- Prior art keywords
- hydrogen
- alkyl
- compound
- reaction
- butanol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 125000002883 imidazolyl group Chemical group 0.000 title description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 40
- 239000001257 hydrogen Substances 0.000 claims abstract description 40
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- -1 imidazolyl compound Chemical class 0.000 claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 180
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 125000006530 (C4-C6) alkyl group Chemical group 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 6
- FELGMEQIXOGIFQ-CYBMUJFWSA-N (3r)-9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1h-carbazol-4-one Chemical compound CC1=NC=CN1C[C@@H]1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FELGMEQIXOGIFQ-CYBMUJFWSA-N 0.000 abstract description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract description 3
- 229960005343 ondansetron Drugs 0.000 abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- NCNFDKWULDWJDS-OAHLLOKOSA-N cilansetron Chemical compound CC1=NC=CN1C[C@@H]1C(=O)C(C=2C=3N4CCCC=3C=CC=2)=C4CC1 NCNFDKWULDWJDS-OAHLLOKOSA-N 0.000 abstract 1
- 229960002099 cilansetron Drugs 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 78
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 17
- 239000012071 phase Substances 0.000 description 16
- 239000002244 precipitate Substances 0.000 description 15
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 10
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 9
- GUQMDNQYMMRJPY-UHFFFAOYSA-N 4,4-dimethyl-1,3-oxazolidine Chemical compound CC1(C)COCN1 GUQMDNQYMMRJPY-UHFFFAOYSA-N 0.000 description 9
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 9
- 229940098779 methanesulfonic acid Drugs 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- UPIKAIAOTXEAAZ-UHFFFAOYSA-N 2-(1,3-oxazolidin-3-yl)ethanol Chemical compound OCCN1CCOC1 UPIKAIAOTXEAAZ-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- HHJUJCWZKJMCLC-UHFFFAOYSA-N 9-methyl-2,3-dihydro-1h-carbazol-4-one Chemical compound C12=CC=CC=C2N(C)C2=C1C(=O)CCC2 HHJUJCWZKJMCLC-UHFFFAOYSA-N 0.000 description 7
- RDRURTGSFBSIKX-UHFFFAOYSA-N 3-ethyl-1,3-oxazolidine Chemical compound CCN1CCOC1 RDRURTGSFBSIKX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 4
- AMLYRCOEFHJSFS-UHFFFAOYSA-N carbazol-1-one Chemical compound C1=CC=C2C3=CC=CC(=O)C3=NC2=C1 AMLYRCOEFHJSFS-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 150000002917 oxazolidines Chemical class 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 1
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010062717 Increased upper airway secretion Diseases 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000003420 antiserotonin agent Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000009615 deamination Effects 0.000 description 1
- 238000006481 deamination reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 208000026435 phlegm Diseases 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D471/06—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02079838 | 2002-11-18 | ||
| PCT/EP2003/050841 WO2004046116A1 (en) | 2002-11-18 | 2003-11-17 | Novel process for the preparation of imidazolyl compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA79655C2 true UA79655C2 (en) | 2007-07-10 |
Family
ID=32319633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UAA200505941A UA79655C2 (en) | 2002-11-18 | 2003-11-17 | Process for the preparation of imidazolyl compounds |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP1565445B1 (pl) |
| JP (1) | JP4611026B2 (pl) |
| KR (1) | KR20050075026A (pl) |
| CN (1) | CN100349873C (pl) |
| AR (1) | AR041955A1 (pl) |
| AT (1) | ATE340783T1 (pl) |
| AU (1) | AU2003296762B2 (pl) |
| BR (1) | BR0316308A (pl) |
| CA (1) | CA2504614C (pl) |
| DE (1) | DE60308720T2 (pl) |
| DK (1) | DK1565445T3 (pl) |
| ES (1) | ES2273088T3 (pl) |
| HR (1) | HRP20050376A2 (pl) |
| IL (1) | IL168258A (pl) |
| MX (1) | MXPA05005261A (pl) |
| NO (1) | NO330342B1 (pl) |
| PL (1) | PL376743A1 (pl) |
| PT (1) | PT1565445E (pl) |
| RU (1) | RU2314296C2 (pl) |
| SA (1) | SA03240414B1 (pl) |
| SI (1) | SI1565445T1 (pl) |
| UA (1) | UA79655C2 (pl) |
| WO (1) | WO2004046116A1 (pl) |
| ZA (1) | ZA200503425B (pl) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3885357T2 (de) * | 1987-06-29 | 1994-03-24 | Duphar Int Res | Anellierte Indolderivate. |
-
2003
- 2003-11-13 AR ARP030104180A patent/AR041955A1/es unknown
- 2003-11-17 SI SI200330519T patent/SI1565445T1/sl unknown
- 2003-11-17 KR KR1020057008864A patent/KR20050075026A/ko not_active Abandoned
- 2003-11-17 MX MXPA05005261A patent/MXPA05005261A/es active IP Right Grant
- 2003-11-17 BR BR0316308-3A patent/BR0316308A/pt not_active Application Discontinuation
- 2003-11-17 UA UAA200505941A patent/UA79655C2/uk unknown
- 2003-11-17 CA CA2504614A patent/CA2504614C/en not_active Expired - Fee Related
- 2003-11-17 EP EP03811396A patent/EP1565445B1/en not_active Expired - Lifetime
- 2003-11-17 JP JP2004552730A patent/JP4611026B2/ja not_active Expired - Fee Related
- 2003-11-17 DE DE60308720T patent/DE60308720T2/de not_active Expired - Lifetime
- 2003-11-17 AT AT03811396T patent/ATE340783T1/de active
- 2003-11-17 WO PCT/EP2003/050841 patent/WO2004046116A1/en not_active Ceased
- 2003-11-17 CN CNB2003801035559A patent/CN100349873C/zh not_active Expired - Fee Related
- 2003-11-17 RU RU2005119155/04A patent/RU2314296C2/ru not_active IP Right Cessation
- 2003-11-17 ES ES03811396T patent/ES2273088T3/es not_active Expired - Lifetime
- 2003-11-17 AU AU2003296762A patent/AU2003296762B2/en not_active Ceased
- 2003-11-17 PT PT03811396T patent/PT1565445E/pt unknown
- 2003-11-17 PL PL376743A patent/PL376743A1/pl not_active Application Discontinuation
- 2003-11-17 HR HR20050376A patent/HRP20050376A2/xx not_active Application Discontinuation
- 2003-11-17 DK DK03811396T patent/DK1565445T3/da active
- 2003-12-03 SA SA03240414A patent/SA03240414B1/ar unknown
-
2005
- 2005-04-27 IL IL168258A patent/IL168258A/en not_active IP Right Cessation
- 2005-04-28 ZA ZA200503425A patent/ZA200503425B/xx unknown
- 2005-06-16 NO NO20052950A patent/NO330342B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE60308720T2 (de) | 2007-01-11 |
| RU2314296C2 (ru) | 2008-01-10 |
| ES2273088T3 (es) | 2007-05-01 |
| BR0316308A (pt) | 2005-09-27 |
| EP1565445A1 (en) | 2005-08-24 |
| CA2504614A1 (en) | 2004-06-03 |
| CA2504614C (en) | 2010-09-28 |
| DK1565445T3 (da) | 2007-01-29 |
| NO330342B1 (no) | 2011-03-28 |
| ATE340783T1 (de) | 2006-10-15 |
| MXPA05005261A (es) | 2005-07-25 |
| AU2003296762A1 (en) | 2004-06-15 |
| DE60308720D1 (de) | 2006-11-09 |
| JP2006512322A (ja) | 2006-04-13 |
| HK1081188A1 (zh) | 2006-05-12 |
| HRP20050376A2 (en) | 2006-02-28 |
| SA03240414B1 (ar) | 2006-12-05 |
| ZA200503425B (en) | 2007-02-28 |
| EP1565445B1 (en) | 2006-09-27 |
| AR041955A1 (es) | 2005-06-01 |
| NO20052950D0 (no) | 2005-06-16 |
| SI1565445T1 (sl) | 2007-02-28 |
| IL168258A (en) | 2010-05-31 |
| CN100349873C (zh) | 2007-11-21 |
| AU2003296762B2 (en) | 2010-03-18 |
| JP4611026B2 (ja) | 2011-01-12 |
| CN1714082A (zh) | 2005-12-28 |
| PL376743A1 (pl) | 2006-01-09 |
| NO20052950L (no) | 2005-08-15 |
| KR20050075026A (ko) | 2005-07-19 |
| RU2005119155A (ru) | 2006-01-20 |
| PT1565445E (pt) | 2007-01-31 |
| WO2004046116A1 (en) | 2004-06-03 |
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