SK17252002A3 - Deriváty acylfenylmočoviny, spôsoby ich výroby a použitie ako liečivo - Google Patents
Deriváty acylfenylmočoviny, spôsoby ich výroby a použitie ako liečivo Download PDFInfo
- Publication number
- SK17252002A3 SK17252002A3 SK1725-2002A SK17252002A SK17252002A3 SK 17252002 A3 SK17252002 A3 SK 17252002A3 SK 17252002 A SK17252002 A SK 17252002A SK 17252002 A3 SK17252002 A3 SK 17252002A3
- Authority
- SK
- Slovakia
- Prior art keywords
- alkyl
- alkylene
- conh
- group
- phenyl
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- 239000003814 drug Substances 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 9
- 150000003672 ureas Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 97
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 148
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 44
- 229910052801 chlorine Inorganic materials 0.000 claims description 44
- 229910052731 fluorine Inorganic materials 0.000 claims description 44
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 36
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- -1 (Οχ-Cg) -alkynyl Chemical group 0.000 claims description 16
- 125000002393 azetidinyl group Chemical group 0.000 claims description 16
- 125000002883 imidazolyl group Chemical group 0.000 claims description 16
- 125000000335 thiazolyl group Chemical group 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000002541 furyl group Chemical group 0.000 claims description 15
- 125000002757 morpholinyl group Chemical group 0.000 claims description 15
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 15
- 239000008280 blood Substances 0.000 claims description 12
- 210000004369 blood Anatomy 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 12
- 125000005936 piperidyl group Chemical group 0.000 claims description 11
- 235000000346 sugar Nutrition 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 238000003776 cleavage reaction Methods 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 230000007017 scission Effects 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 3
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 3
- ROMNEYAQUBNRLR-UHFFFAOYSA-N 2-(4-hydroxybiphenyl-3-yl)-4-methyl-1h-isoindole-1,3(2h)-dione Chemical compound O=C1C=2C(C)=CC=CC=2C(=O)N1C(C(=CC=1)O)=CC=1C1=CC=CC=C1 ROMNEYAQUBNRLR-UHFFFAOYSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 3
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 1
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- 125000004650 C1-C8 alkynyl group Chemical group 0.000 claims 1
- 229910002514 Co–Co Inorganic materials 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
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- 239000000243 solution Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- HXXFSFRBOHSIMQ-VFUOTHLCSA-N alpha-D-glucose 1-phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1O HXXFSFRBOHSIMQ-VFUOTHLCSA-N 0.000 description 4
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Classifications
-
- 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
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- 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
- 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
- C07D307/38—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 substituted hydrocarbon radicals attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10028175 | 2000-06-09 | ||
| DE2001116768 DE10116768A1 (de) | 2001-04-04 | 2001-04-04 | Acylphenylharnstoffderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| PCT/EP2001/006030 WO2001094300A1 (de) | 2000-06-09 | 2001-05-26 | Acylphenylharnstoffderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK17252002A3 true SK17252002A3 (sk) | 2003-05-02 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1725-2002A SK17252002A3 (sk) | 2000-06-09 | 2001-05-26 | Deriváty acylfenylmočoviny, spôsoby ich výroby a použitie ako liečivo |
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| Country | Link |
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| US (1) | US6506778B2 (enExample) |
| EP (1) | EP1294682B1 (enExample) |
| JP (1) | JP4510372B2 (enExample) |
| KR (1) | KR20030007934A (enExample) |
| CN (1) | CN1280266C (enExample) |
| AR (1) | AR030230A1 (enExample) |
| AT (1) | ATE265424T1 (enExample) |
| AU (2) | AU2001262318B2 (enExample) |
| BR (1) | BR0111457A (enExample) |
| CA (1) | CA2411082A1 (enExample) |
| CZ (1) | CZ20024003A3 (enExample) |
| DE (1) | DE50102147D1 (enExample) |
| DK (1) | DK1294682T3 (enExample) |
| EE (1) | EE200200634A (enExample) |
| ES (1) | ES2215902T3 (enExample) |
| HR (1) | HRP20020968A2 (enExample) |
| HU (1) | HUP0301749A2 (enExample) |
| IL (1) | IL153273A0 (enExample) |
| MX (1) | MXPA02011458A (enExample) |
| NO (1) | NO20025879L (enExample) |
| NZ (1) | NZ523034A (enExample) |
| PL (1) | PL359178A1 (enExample) |
| PT (1) | PT1294682E (enExample) |
| SK (1) | SK17252002A3 (enExample) |
| TR (1) | TR200401029T4 (enExample) |
| WO (1) | WO2001094300A1 (enExample) |
| YU (1) | YU91002A (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20021091A1 (es) | 2001-05-25 | 2003-02-04 | Aventis Pharma Gmbh | Derivados de fenilurea sustituidos con carbonamida y procedimiento para su preparacion |
| DE10125567B4 (de) * | 2001-05-25 | 2004-08-26 | Aventis Pharma Deutschland Gmbh | Carbonamid substituierte Phenylharnstoffderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE10139416A1 (de) * | 2001-08-17 | 2003-03-06 | Aventis Pharma Gmbh | Aminoalkyl substituierte aromatische Bicyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| GB0205165D0 (en) | 2002-03-06 | 2002-04-17 | Astrazeneca Ab | Chemical compounds |
| GB0205176D0 (en) | 2002-03-06 | 2002-04-17 | Astrazeneca Ab | Chemical compounds |
| GB0205162D0 (en) | 2002-03-06 | 2002-04-17 | Astrazeneca Ab | Chemical compounds |
| GB0205166D0 (en) | 2002-03-06 | 2002-04-17 | Astrazeneca Ab | Chemical compounds |
| GB0205175D0 (en) | 2002-03-06 | 2002-04-17 | Astrazeneca Ab | Chemical compounds |
| GB0205170D0 (en) | 2002-03-06 | 2002-04-17 | Astrazeneca Ab | Chemical compounds |
| US7078404B2 (en) | 2002-04-11 | 2006-07-18 | Sanofi-Aventis Deutschland Gmbh | Acyl-3-carboxyphenylurea derivatives, processes for preparing them and their use |
| US7223796B2 (en) | 2002-04-11 | 2007-05-29 | Sanofi-Aventis Deutschland Gmbh | Acyl-4-carboxyphenylurea derivatives, processes for preparing them and their use |
| IL164249A0 (en) * | 2002-04-11 | 2005-12-18 | Aventis Pharma Gmbh | Acyl-3-carboxphenylurea derivatives, processes forpreparing them and their use |
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| CH516578A (de) * | 1967-11-02 | 1971-12-15 | Bayer Ag | Verfahren zur Herstellung von heterocyclische Acylaminogruppen enthaltenden Arylsulfonylharnstoffen mit blutdrucksenkender Wirkung |
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| EP0167197B1 (en) * | 1984-07-05 | 1989-01-18 | Duphar International Research B.V | Benzoylurea compounds, and insecticidal and acaricidal compositions comprising same |
| DE3504749A1 (de) * | 1985-02-08 | 1986-08-14 | Schering AG, 1000 Berlin und 4709 Bergkamen | Acylharnstoffe, insektizide mittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung |
| JPH0791248B2 (ja) * | 1988-06-29 | 1995-10-04 | 富士写真フイルム株式会社 | アルコキシもしくはアリールオキシベンゼン化合物の製造方法 |
| DE4208778C1 (enExample) * | 1992-03-17 | 1993-09-23 | Schering Ag Berlin Und Bergkamen, 13353 Berlin, De | |
| GB9313268D0 (en) * | 1993-06-28 | 1993-08-11 | Zeneca Ltd | Chemical compounds |
-
2001
- 2001-05-26 NZ NZ523034A patent/NZ523034A/en unknown
- 2001-05-26 EE EEP200200634A patent/EE200200634A/xx unknown
- 2001-05-26 PL PL01359178A patent/PL359178A1/xx not_active Application Discontinuation
- 2001-05-26 AU AU2001262318A patent/AU2001262318B2/en not_active Ceased
- 2001-05-26 JP JP2002501817A patent/JP4510372B2/ja not_active Expired - Fee Related
- 2001-05-26 TR TR2004/01029T patent/TR200401029T4/xx unknown
- 2001-05-26 ES ES01936399T patent/ES2215902T3/es not_active Expired - Lifetime
- 2001-05-26 DK DK01936399T patent/DK1294682T3/da active
- 2001-05-26 SK SK1725-2002A patent/SK17252002A3/sk unknown
- 2001-05-26 CZ CZ20024003A patent/CZ20024003A3/cs unknown
- 2001-05-26 AU AU6231801A patent/AU6231801A/xx active Pending
- 2001-05-26 CA CA002411082A patent/CA2411082A1/en not_active Abandoned
- 2001-05-26 AT AT01936399T patent/ATE265424T1/de not_active IP Right Cessation
- 2001-05-26 KR KR1020027016791A patent/KR20030007934A/ko not_active Ceased
- 2001-05-26 IL IL15327301A patent/IL153273A0/xx unknown
- 2001-05-26 PT PT01936399T patent/PT1294682E/pt unknown
- 2001-05-26 WO PCT/EP2001/006030 patent/WO2001094300A1/de not_active Ceased
- 2001-05-26 YU YU91002A patent/YU91002A/sh unknown
- 2001-05-26 DE DE50102147T patent/DE50102147D1/de not_active Expired - Lifetime
- 2001-05-26 MX MXPA02011458A patent/MXPA02011458A/es active IP Right Grant
- 2001-05-26 HU HU0301749A patent/HUP0301749A2/hu unknown
- 2001-05-26 HR HR20020968A patent/HRP20020968A2/xx not_active Application Discontinuation
- 2001-05-26 CN CNB018108016A patent/CN1280266C/zh not_active Expired - Fee Related
- 2001-05-26 EP EP01936399A patent/EP1294682B1/de not_active Expired - Lifetime
- 2001-05-26 BR BR0111457-3A patent/BR0111457A/pt not_active IP Right Cessation
- 2001-06-07 AR ARP010102735A patent/AR030230A1/es unknown
- 2001-06-08 US US09/875,901 patent/US6506778B2/en not_active Expired - Lifetime
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2002
- 2002-12-06 NO NO20025879A patent/NO20025879L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IL153273A0 (en) | 2003-07-06 |
| BR0111457A (pt) | 2003-06-24 |
| ES2215902T3 (es) | 2004-10-16 |
| HRP20020968A2 (en) | 2005-02-28 |
| NZ523034A (en) | 2004-07-30 |
| HK1056715A1 (en) | 2004-02-27 |
| PT1294682E (pt) | 2004-09-30 |
| HUP0301749A2 (hu) | 2003-09-29 |
| CZ20024003A3 (cs) | 2003-03-12 |
| ATE265424T1 (de) | 2004-05-15 |
| KR20030007934A (ko) | 2003-01-23 |
| DE50102147D1 (de) | 2004-06-03 |
| AU2001262318B2 (en) | 2005-09-08 |
| JP2003535843A (ja) | 2003-12-02 |
| MXPA02011458A (es) | 2003-04-25 |
| AR030230A1 (es) | 2003-08-13 |
| EE200200634A (et) | 2004-04-15 |
| WO2001094300A1 (de) | 2001-12-13 |
| EP1294682A1 (de) | 2003-03-26 |
| JP4510372B2 (ja) | 2010-07-21 |
| CN1434796A (zh) | 2003-08-06 |
| US20020151586A1 (en) | 2002-10-17 |
| US6506778B2 (en) | 2003-01-14 |
| EP1294682B1 (de) | 2004-04-28 |
| NO20025879D0 (no) | 2002-12-06 |
| NO20025879L (no) | 2003-01-29 |
| CN1280266C (zh) | 2006-10-18 |
| DK1294682T3 (da) | 2004-08-02 |
| AU6231801A (en) | 2001-12-17 |
| PL359178A1 (en) | 2004-08-23 |
| YU91002A (sh) | 2006-05-25 |
| TR200401029T4 (tr) | 2004-06-21 |
| CA2411082A1 (en) | 2002-12-05 |
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