JP4398859B2 - Ｎ−ベンゾイルウレイド桂皮酸誘導体、それらの製造法、およびそれらの使用 - Google Patents
Ｎ−ベンゾイルウレイド桂皮酸誘導体、それらの製造法、およびそれらの使用 Download PDFInfo
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- JP4398859B2 JP4398859B2 JP2004511258A JP2004511258A JP4398859B2 JP 4398859 B2 JP4398859 B2 JP 4398859B2 JP 2004511258 A JP2004511258 A JP 2004511258A JP 2004511258 A JP2004511258 A JP 2004511258A JP 4398859 B2 JP4398859 B2 JP 4398859B2
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- acid
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- -1 N-benzoylureido cinnamic acid derivatives Chemical class 0.000 title description 15
- 238000002360 preparation method Methods 0.000 title description 6
- 238000000034 method Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 110
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000008280 blood Substances 0.000 claims description 6
- 210000004369 blood Anatomy 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 5
- 239000008103 glucose Substances 0.000 claims description 5
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 4
- 230000003178 anti-diabetic effect Effects 0.000 abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 41
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 26
- 239000000203 mixture Substances 0.000 description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
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- 239000000556 agonist Substances 0.000 description 16
- 125000000623 heterocyclic group Chemical group 0.000 description 16
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 15
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 14
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 14
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 10
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 4
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- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 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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- 229940039781 leptin Drugs 0.000 description 4
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 description 4
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- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 4
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- QYMOTVAZPUDFFL-UHFFFAOYSA-N methyl 4-amino-3-(3-methoxy-3-oxoprop-1-enyl)benzoate Chemical compound COC(=O)C=CC1=CC(C(=O)OC)=CC=C1N QYMOTVAZPUDFFL-UHFFFAOYSA-N 0.000 description 3
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- LYAUICDWKQJAGX-UHFFFAOYSA-N n-(7-hydroxy-2,2,4,6-tetramethyl-1,3-dihydroinden-1-yl)-2-[4-(3-methoxyphenyl)piperazin-1-yl]acetamide Chemical compound COC1=CC=CC(N2CCN(CC(=O)NC3C(CC4=C3C(=C(C)C=C4C)O)(C)C)CC2)=C1 LYAUICDWKQJAGX-UHFFFAOYSA-N 0.000 description 1
- LXEDKSZTPGCEPU-UHFFFAOYSA-N n-[2-(3a-benzyl-2-methyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl)-1-(4-chlorophenyl)-2-oxoethyl]-1-amino-1,2,3,4-tetrahydronaphthalene-2-carboxamide Chemical compound O=C1N(C)N=C2CCN(C(=O)C(NC(=O)C3C(C4=CC=CC=C4CC3)N)C=3C=CC(Cl)=CC=3)CC21CC1=CC=CC=C1 LXEDKSZTPGCEPU-UHFFFAOYSA-N 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 230000002474 noradrenergic effect Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 108060005714 orexin Proteins 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- YDCVQGAUCOROHB-UHFFFAOYSA-N oxadiazolidine-4,5-dione Chemical class O=C1NNOC1=O YDCVQGAUCOROHB-UHFFFAOYSA-N 0.000 description 1
- VWMZIGBYZQUQOA-QEEMJVPDSA-N pamaqueside Chemical compound O([C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4C[C@H]5[C@@H]([C@]4(CC(=O)[C@@H]3[C@@]2(C)CC1)C)[C@@H]([C@]1(OC[C@H](C)CC1)O5)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VWMZIGBYZQUQOA-QEEMJVPDSA-N 0.000 description 1
- 229950005482 pamaqueside Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000001050 pharmacotherapy Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229960003562 phentermine Drugs 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229940100467 polyvinyl acetate phthalate Drugs 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 229960002965 pravastatin Drugs 0.000 description 1
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000009103 reabsorption Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229960000672 rosuvastatin Drugs 0.000 description 1
- 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
- 201000000980 schizophrenia Diseases 0.000 description 1
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical class C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 1
- 239000000952 serotonin receptor agonist Substances 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 229960004425 sibutramine Drugs 0.000 description 1
- 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
- 229960002855 simvastatin Drugs 0.000 description 1
- 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
- 210000003491 skin Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000004059 squalene synthase inhibitor Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000001467 thiazolidinediones Chemical class 0.000 description 1
- 229950004437 tiqueside Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
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
- C07C275/46—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
-
- 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
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Diabetes (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Hematology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Obesity (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Epidemiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10225635A DE10225635C1 (de) | 2002-06-07 | 2002-06-07 | N-Benzoylureido-Zimtsäurederivate, Verfahren zu deren Herstellung und deren Verwendung |
| PCT/EP2003/005355 WO2003104188A1 (de) | 2002-06-07 | 2003-05-22 | N-benzoylureido-zimtsäurederivate, verfahren zu deren herstellung und deren verwendung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005529164A JP2005529164A (ja) | 2005-09-29 |
| JP2005529164A5 JP2005529164A5 (enExample) | 2006-06-22 |
| JP4398859B2 true JP4398859B2 (ja) | 2010-01-13 |
Family
ID=29594346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004511258A Expired - Fee Related JP4398859B2 (ja) | 2002-06-07 | 2003-05-22 | Ｎ−ベンゾイルウレイド桂皮酸誘導体、それらの製造法、およびそれらの使用 |
Country Status (26)
| Country | Link |
|---|---|
| EP (1) | EP1513800B1 (enExample) |
| JP (1) | JP4398859B2 (enExample) |
| KR (1) | KR20050004295A (enExample) |
| CN (1) | CN1659137A (enExample) |
| AT (1) | ATE345326T1 (enExample) |
| AU (1) | AU2003238373A1 (enExample) |
| BR (1) | BR0311646A (enExample) |
| CA (1) | CA2488760A1 (enExample) |
| CY (1) | CY1106003T1 (enExample) |
| DE (2) | DE10225635C1 (enExample) |
| DK (1) | DK1513800T3 (enExample) |
| ES (1) | ES2277082T3 (enExample) |
| HR (1) | HRPK20041161B3 (enExample) |
| IL (1) | IL165558A0 (enExample) |
| IN (1) | IN2004CH02747A (enExample) |
| MA (1) | MA27232A1 (enExample) |
| MX (1) | MXPA04011984A (enExample) |
| NO (1) | NO20050087L (enExample) |
| NZ (1) | NZ537004A (enExample) |
| PL (1) | PL372117A1 (enExample) |
| PT (1) | PT1513800E (enExample) |
| RU (1) | RU2004139122A (enExample) |
| SI (1) | SI1513800T1 (enExample) |
| TW (1) | TW200404763A (enExample) |
| WO (1) | WO2003104188A1 (enExample) |
| ZA (1) | ZA200408887B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7179941B2 (en) | 2003-01-23 | 2007-02-20 | Sanofi-Aventis Deutschland Gmbh | Carbonylamino-substituted acyl phenyl urea derivatives, process for their preparation and their use |
| DE10302452B4 (de) * | 2003-01-23 | 2005-02-24 | Aventis Pharma Deutschland Gmbh | Carbonylamino-substituierte Acyl-phenyl-harnstoffderivate, Verfahren zu deren Herstellung und deren Verwendung |
| DE10306502B4 (de) * | 2003-02-17 | 2005-03-17 | Aventis Pharma Deutschland Gmbh | Substituierte 3-(Benzoylureido)-thiophenderivate und sie enthaltende Arzneimittel |
| DE10308351A1 (de) | 2003-02-27 | 2004-11-25 | Aventis Pharma Deutschland Gmbh | 1,3-substituierte Cycloalkylderivate mit sauren, meist heterocyclischen Gruppen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE10308352A1 (de) | 2003-02-27 | 2004-09-09 | Aventis Pharma Deutschland Gmbh | Arylcycloalkylderivate mit verzweigten Seitenketten, Verfahren zu ihrer Herstellung und ihre Anwendung als Arzneimittel |
| US7148246B2 (en) | 2003-02-27 | 2006-12-12 | Sanofi-Aventis Deutschland Gmbh | Cycloalkyl derivatives having bioisosteric carboxylic acid groups, processes for their preparation and their use as pharmaceuticals |
| DE10308355A1 (de) | 2003-02-27 | 2004-12-23 | Aventis Pharma Deutschland Gmbh | Aryl-cycloalkyl substituierte Alkansäurederivate, Verfahren zu ihrer Herstellung und ihre Anwendung als Arzneimittel |
| DE10308353A1 (de) | 2003-02-27 | 2004-12-02 | Aventis Pharma Deutschland Gmbh | Diarylcycloalkylderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE10335092B3 (de) * | 2003-08-01 | 2005-02-03 | Aventis Pharma Deutschland Gmbh | Substituierte Benzoylureido-o-benzoylamide, Verfahren zu deren Herstellung und deren Verwendung |
| US7241787B2 (en) | 2004-01-25 | 2007-07-10 | Sanofi-Aventis Deutschland Gmbh | Substituted N-cycloexylimidazolinones, process for their preparation and their use as medicaments |
| EP1586573B1 (en) | 2004-04-01 | 2007-02-07 | Sanofi-Aventis Deutschland GmbH | Oxadiazolones, processes for their preparation and their use as pharmaceuticals |
| US7223786B2 (en) | 2004-11-15 | 2007-05-29 | Bristol-Myers Squibb Company | 2-aminonaphthalene derivatives and related glycogen phosphorylase inhibitors |
| US7226942B2 (en) | 2004-11-15 | 2007-06-05 | Bristol-Myers Squibb Company | 2-amino-4-functionalized tetralin derivatives and related glycogen phosphorylase inhibitors |
| WO2006053274A2 (en) | 2004-11-15 | 2006-05-18 | Bristol-Myers Squibb Company | 2-amino-1-functionalized tetralin derivatives and related glycogen phosphorylase inhibitors |
| US7365061B2 (en) | 2004-11-15 | 2008-04-29 | Bristol-Myers Squibb Company | 2-Amino-3-functionalized tetralin derivatives and related glycogen phosphorylase inhibitors |
| DE102005026762A1 (de) | 2005-06-09 | 2006-12-21 | Sanofi-Aventis Deutschland Gmbh | Azolopyridin-2-on-derivate als Inhibitoren von Lipasen und Phospholipasen |
| TW200718691A (en) * | 2005-06-10 | 2007-05-16 | Sigma Tau Ind Farmaceuti | Cinnamic and phenylpropiolic acid derivatives useful as anti-tumour agents |
| PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL141381B (nl) * | 1963-09-25 | 1974-03-15 | Hoechst Ag | Werkwijze voor het bereiden van geneesmiddelen met bloedsuikerspiegel verlagende werkzaamheid. |
| AU601145B2 (en) * | 1985-03-01 | 1990-09-06 | Duphar International Research B.V. | Benzoyl urea derivatives having anti-tumor activity |
| ZA867420B (en) * | 1985-09-30 | 1987-05-27 | Union Carbide Corp | Pesticidal 1-(4-aryloxyphenyl)-3-benzoyl urea compounds and process for preparation |
| DE4037112A1 (de) * | 1990-11-22 | 1992-05-27 | Thomae Gmbh Dr K | Neue pyridylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| GB9313268D0 (en) * | 1993-06-28 | 1993-08-11 | Zeneca Ltd | Chemical compounds |
| US6297269B1 (en) * | 1995-06-06 | 2001-10-02 | Pfizer Inc. | Substituted n-(indole-2-carbonyl-) amides and derivatives as glycogen phosphorylase inhibitors |
| AR028253A1 (es) * | 2000-03-16 | 2003-04-30 | Pfizer Prod Inc | Inhibidores de la glucogeno fosforilasa |
| NZ523034A (en) * | 2000-06-09 | 2004-07-30 | Aventis Pharma Gmbh | Acylphenyl urea derivatives, methods for the production thereof and use thereof as a medicament |
| GB0021831D0 (en) * | 2000-09-06 | 2000-10-18 | Astrazeneca Ab | Chemical compounds |
-
2002
- 2002-06-07 DE DE10225635A patent/DE10225635C1/de not_active Expired - Fee Related
-
2003
- 2003-05-22 DE DE50305693T patent/DE50305693D1/de not_active Expired - Lifetime
- 2003-05-22 PT PT03732438T patent/PT1513800E/pt unknown
- 2003-05-22 AT AT03732438T patent/ATE345326T1/de not_active IP Right Cessation
- 2003-05-22 MX MXPA04011984A patent/MXPA04011984A/es unknown
- 2003-05-22 SI SI200330635T patent/SI1513800T1/sl unknown
- 2003-05-22 RU RU2004139122/04A patent/RU2004139122A/ru not_active Application Discontinuation
- 2003-05-22 DK DK03732438T patent/DK1513800T3/da active
- 2003-05-22 HR HR20041161A patent/HRPK20041161B3/xx not_active IP Right Cessation
- 2003-05-22 NZ NZ537004A patent/NZ537004A/en unknown
- 2003-05-22 EP EP03732438A patent/EP1513800B1/de not_active Expired - Lifetime
- 2003-05-22 JP JP2004511258A patent/JP4398859B2/ja not_active Expired - Fee Related
- 2003-05-22 PL PL03372117A patent/PL372117A1/xx not_active Application Discontinuation
- 2003-05-22 ES ES03732438T patent/ES2277082T3/es not_active Expired - Lifetime
- 2003-05-22 CN CN038131730A patent/CN1659137A/zh active Pending
- 2003-05-22 WO PCT/EP2003/005355 patent/WO2003104188A1/de not_active Ceased
- 2003-05-22 AU AU2003238373A patent/AU2003238373A1/en not_active Abandoned
- 2003-05-22 BR BR0311646-8A patent/BR0311646A/pt not_active IP Right Cessation
- 2003-05-22 CA CA002488760A patent/CA2488760A1/en not_active Abandoned
- 2003-05-22 KR KR20047019866A patent/KR20050004295A/ko not_active Withdrawn
- 2003-06-05 TW TW92115159A patent/TW200404763A/zh unknown
-
2004
- 2004-11-03 ZA ZA200408887A patent/ZA200408887B/en unknown
- 2004-11-16 MA MA27950A patent/MA27232A1/fr unknown
- 2004-12-05 IL IL16555804A patent/IL165558A0/xx unknown
- 2004-12-06 IN IN2747CH2004 patent/IN2004CH02747A/en unknown
-
2005
- 2005-01-06 NO NO20050087A patent/NO20050087L/no not_active Application Discontinuation
-
2007
- 2007-02-09 CY CY20071100177T patent/CY1106003T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RU2004139122A (ru) | 2005-06-10 |
| DK1513800T3 (da) | 2007-03-26 |
| ZA200408887B (en) | 2005-11-23 |
| MXPA04011984A (es) | 2005-03-07 |
| CY1106003T1 (el) | 2011-04-06 |
| DE50305693D1 (de) | 2006-12-28 |
| KR20050004295A (ko) | 2005-01-12 |
| WO2003104188A1 (de) | 2003-12-18 |
| SI1513800T1 (sl) | 2007-04-30 |
| PT1513800E (pt) | 2007-02-28 |
| MA27232A1 (fr) | 2005-02-01 |
| NZ537004A (en) | 2006-06-30 |
| EP1513800B1 (de) | 2006-11-15 |
| IN2004CH02747A (enExample) | 2006-02-10 |
| TW200404763A (en) | 2004-04-01 |
| CA2488760A1 (en) | 2003-12-18 |
| HRPK20041161B3 (en) | 2006-09-30 |
| CN1659137A (zh) | 2005-08-24 |
| IL165558A0 (en) | 2006-01-15 |
| NO20050087L (no) | 2005-01-06 |
| EP1513800A1 (de) | 2005-03-16 |
| DE10225635C1 (de) | 2003-12-24 |
| BR0311646A (pt) | 2005-03-15 |
| AU2003238373A1 (en) | 2003-12-22 |
| ES2277082T3 (es) | 2007-07-01 |
| PL372117A1 (en) | 2005-07-11 |
| ATE345326T1 (de) | 2006-12-15 |
| HRP20041161A2 (en) | 2005-04-30 |
| JP2005529164A (ja) | 2005-09-29 |
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