KR20050104351A - 카보닐-아미노 치환된 아실 페닐 우레아 유도체, 이의제조방법 및 이의 용도 - Google Patents
카보닐-아미노 치환된 아실 페닐 우레아 유도체, 이의제조방법 및 이의 용도 Download PDFInfo
- Publication number
- KR20050104351A KR20050104351A KR1020057013500A KR20057013500A KR20050104351A KR 20050104351 A KR20050104351 A KR 20050104351A KR 1020057013500 A KR1020057013500 A KR 1020057013500A KR 20057013500 A KR20057013500 A KR 20057013500A KR 20050104351 A KR20050104351 A KR 20050104351A
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- KR
- South Korea
- Prior art keywords
- alkyl
- alkenyl
- alkynyl
- alkylene
- cycloalkyl
- 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.)
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- -1 acyl phenyl urea derivatives Chemical class 0.000 title claims description 46
- 238000000034 method Methods 0.000 title claims description 12
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 102
- 150000003839 salts Chemical class 0.000 claims abstract description 14
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- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 61
- 229910052801 chlorine Inorganic materials 0.000 claims description 42
- 229910052731 fluorine Inorganic materials 0.000 claims description 38
- 239000004480 active ingredient Substances 0.000 claims description 28
- 229910052794 bromium Inorganic materials 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 16
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 12
- 229910004013 NO 2 Inorganic materials 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 10
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 239000008280 blood Substances 0.000 claims description 8
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
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- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
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- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 description 1
- 230000000862 serotonergic effect Effects 0.000 description 1
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- UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
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- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
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- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
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- 150000003892 tartrate salts Chemical class 0.000 description 1
- ZAOPBCHLHBOUPR-UHFFFAOYSA-N tert-butyl 1-[2-[di(propan-2-yl)amino]ethylcarbamoyl]-6-phenylmethoxy-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound C=1C=C2C(C(=O)NCCN(C(C)C)C(C)C)N(C(=O)OC(C)(C)C)CCC2=CC=1OCC1=CC=CC=C1 ZAOPBCHLHBOUPR-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/48—Y being a hydrogen or a carbon atom
- C07C275/54—Y being a carbon atom of a six-membered aromatic ring, e.g. benzoylureas
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/033—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- 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
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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 ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Obesity (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Indole Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10302452.2 | 2003-01-23 | ||
| DE10302452A DE10302452B4 (de) | 2003-01-23 | 2003-01-23 | Carbonylamino-substituierte Acyl-phenyl-harnstoffderivate, Verfahren zu deren Herstellung und deren Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20050104351A true KR20050104351A (ko) | 2005-11-02 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020057013500A Withdrawn KR20050104351A (ko) | 2003-01-23 | 2004-01-07 | 카보닐-아미노 치환된 아실 페닐 우레아 유도체, 이의제조방법 및 이의 용도 |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP1590322B1 (https=) |
| JP (1) | JP4557963B2 (https=) |
| KR (1) | KR20050104351A (https=) |
| CN (1) | CN1798730A (https=) |
| AT (1) | ATE443697T1 (https=) |
| AU (1) | AU2004205352A1 (https=) |
| BR (1) | BRPI0406840A (https=) |
| CA (1) | CA2513286A1 (https=) |
| CO (1) | CO5690542A2 (https=) |
| DE (2) | DE10302452B4 (https=) |
| HR (1) | HRP20050667A2 (https=) |
| MA (1) | MA27649A1 (https=) |
| MX (1) | MXPA05007515A (https=) |
| NO (1) | NO20053876L (https=) |
| PL (1) | PL376456A1 (https=) |
| RU (1) | RU2005126606A (https=) |
| WO (1) | WO2004065356A1 (https=) |
| ZA (1) | ZA200504647B (https=) |
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| JP5385605B2 (ja) * | 2005-03-11 | 2014-01-08 | 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 | Ａｔｐ結合カセットトランスポーターのモジュレーター |
| PE20110235A1 (es) | 2006-05-04 | 2011-04-14 | Boehringer Ingelheim Int | Combinaciones farmaceuticas que comprenden linagliptina y metmorfina |
| WO2009081892A1 (ja) * | 2007-12-25 | 2009-07-02 | Kissei Pharmaceutical Co., Ltd. | 新規なカテコール誘導体、それを含有する医薬組成物およびそれらの用途 |
| EP2543660A4 (en) | 2010-03-04 | 2014-04-30 | Ajinomoto Kk | PROPHYLACTIC OR THERAPEUTIC ACTIVE AGAINST DIABETES OR ADIPOSITAS |
| GB201223308D0 (en) | 2012-12-21 | 2013-02-06 | Univ Sunderland | Enzyme inhibitors |
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| CH508019A (de) * | 1968-12-12 | 1971-05-31 | Ciba Geigy Ag | Verfahren zur Herstellung neuer Azofarbstoffpigmente |
| EP0116729B1 (en) * | 1983-01-24 | 1988-10-12 | Duphar International Research B.V | Benzoylurea compounds and pesticidal compositions comprisingsame |
| AU601145B2 (en) * | 1985-03-01 | 1990-09-06 | Duphar International Research B.V. | Benzoyl urea derivatives having anti-tumor activity |
| EP0324521A3 (en) * | 1988-01-11 | 1991-11-27 | Duphar International Research B.V | Method of treating haematologic diseases and pharmaceutical compositions to be used therefor |
| TWI238064B (en) * | 1995-06-20 | 2005-08-21 | Takeda Chemical Industries Ltd | A pharmaceutical composition for prophylaxis and treatment of diabetes |
| WO1999046236A1 (en) * | 1998-03-12 | 1999-09-16 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (ptpases) |
| CA2338121A1 (en) * | 1998-08-04 | 2000-02-17 | Astrazeneca Ab | Amide derivatives useful as inhibitors of the production of cytokines |
| GB0001662D0 (en) * | 1999-02-06 | 2000-03-15 | Zeneca Ltd | Pharmaceutical compositions |
| TR200401029T4 (tr) * | 2000-06-09 | 2004-06-21 | Aventis Pharma Deutschland Gmbh | Asilfenil-üre türevleri, imalat yöntemleri ve ilaç maddesi olarak kullanımları |
| PE20021091A1 (es) * | 2001-05-25 | 2003-02-04 | Aventis Pharma Gmbh | Derivados de fenilurea sustituidos con carbonamida y procedimiento para su preparacion |
| DE10225635C1 (de) * | 2002-06-07 | 2003-12-24 | Aventis Pharma Gmbh | N-Benzoylureido-Zimtsäurederivate, Verfahren zu deren Herstellung und deren Verwendung |
-
2003
- 2003-01-23 DE DE10302452A patent/DE10302452B4/de not_active Expired - Fee Related
-
2004
- 2004-01-07 CA CA002513286A patent/CA2513286A1/en not_active Abandoned
- 2004-01-07 WO PCT/EP2004/000041 patent/WO2004065356A1/de not_active Ceased
- 2004-01-07 MX MXPA05007515A patent/MXPA05007515A/es not_active Application Discontinuation
- 2004-01-07 EP EP04700448A patent/EP1590322B1/de not_active Expired - Lifetime
- 2004-01-07 RU RU2005126606/04A patent/RU2005126606A/ru not_active Application Discontinuation
- 2004-01-07 PL PL04376456A patent/PL376456A1/xx not_active Application Discontinuation
- 2004-01-07 DE DE502004010108T patent/DE502004010108D1/de not_active Expired - Lifetime
- 2004-01-07 AU AU2004205352A patent/AU2004205352A1/en not_active Abandoned
- 2004-01-07 JP JP2006500523A patent/JP4557963B2/ja not_active Expired - Fee Related
- 2004-01-07 CN CNA200480002674XA patent/CN1798730A/zh active Pending
- 2004-01-07 AT AT04700448T patent/ATE443697T1/de not_active IP Right Cessation
- 2004-01-07 KR KR1020057013500A patent/KR20050104351A/ko not_active Withdrawn
- 2004-01-07 BR BR0406840-8A patent/BRPI0406840A/pt not_active IP Right Cessation
- 2004-01-07 HR HR20050667A patent/HRP20050667A2/xx not_active Application Discontinuation
-
2005
- 2005-06-07 ZA ZA200504647A patent/ZA200504647B/en unknown
- 2005-07-21 CO CO05071890A patent/CO5690542A2/es not_active Application Discontinuation
- 2005-07-22 MA MA28408A patent/MA27649A1/fr unknown
- 2005-08-18 NO NO20053876A patent/NO20053876L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE10302452A1 (de) | 2004-08-12 |
| WO2004065356A1 (de) | 2004-08-05 |
| MXPA05007515A (es) | 2006-01-27 |
| JP4557963B2 (ja) | 2010-10-06 |
| DE10302452B4 (de) | 2005-02-24 |
| MA27649A1 (fr) | 2005-12-01 |
| CN1798730A (zh) | 2006-07-05 |
| NO20053876D0 (no) | 2005-08-18 |
| EP1590322A1 (de) | 2005-11-02 |
| ZA200504647B (en) | 2006-04-26 |
| ATE443697T1 (de) | 2009-10-15 |
| CA2513286A1 (en) | 2004-08-05 |
| RU2005126606A (ru) | 2006-01-20 |
| BRPI0406840A (pt) | 2005-12-13 |
| PL376456A1 (en) | 2005-12-27 |
| JP2006516971A (ja) | 2006-07-13 |
| AU2004205352A1 (en) | 2004-08-05 |
| EP1590322B1 (de) | 2009-09-23 |
| DE502004010108D1 (de) | 2009-11-05 |
| NO20053876L (no) | 2005-10-12 |
| CO5690542A2 (es) | 2006-10-31 |
| HRP20050667A2 (en) | 2006-09-30 |
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| PC1203 | Withdrawal of no request for examination | ||
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