AU2001289675B2 - Novel heteroaryl derivatives and the use thereof as pharmaceuticals - Google Patents
Novel heteroaryl derivatives and the use thereof as pharmaceuticals Download PDFInfo
- Publication number
- AU2001289675B2 AU2001289675B2 AU2001289675A AU2001289675A AU2001289675B2 AU 2001289675 B2 AU2001289675 B2 AU 2001289675B2 AU 2001289675 A AU2001289675 A AU 2001289675A AU 2001289675 A AU2001289675 A AU 2001289675A AU 2001289675 B2 AU2001289675 B2 AU 2001289675B2
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- mono
- radical
- group
- alkylamino
- 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.)
- Ceased
Links
- 239000003814 drug Substances 0.000 title claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 title claims description 6
- -1 nitro, amino Chemical group 0.000 claims description 298
- 229910052736 halogen Inorganic materials 0.000 claims description 134
- 150000002367 halogens Chemical class 0.000 claims description 134
- 125000001424 substituent group Chemical group 0.000 claims description 126
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 72
- 229910052739 hydrogen Inorganic materials 0.000 claims description 71
- 239000001257 hydrogen Substances 0.000 claims description 71
- 125000001153 fluoro group Chemical group F* 0.000 claims description 65
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 61
- 229910052731 fluorine Inorganic materials 0.000 claims description 60
- 239000011737 fluorine Substances 0.000 claims description 60
- 125000004043 oxo group Chemical group O=* 0.000 claims description 60
- 150000001251 acridines Chemical class 0.000 claims description 44
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 39
- 229940027998 antiseptic and disinfectant acridine derivative Drugs 0.000 claims description 37
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- 150000003254 radicals Chemical class 0.000 claims description 17
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004941 pyridazin-5-yl group Chemical group N1=NC=CC(=C1)* 0.000 claims description 4
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 4
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 3
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QCVGMYKWTIPJGT-UHFFFAOYSA-N [C].C1=CC=CC2=NC3=CC=CC=C3C=C12 Chemical group [C].C1=CC=CC2=NC3=CC=CC=C3C=C12 QCVGMYKWTIPJGT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- OOGYVVYCCYJADG-UHFFFAOYSA-N acridine-1-carboxylic acid Chemical compound C1=CC=C2C=C3C(C(=O)O)=CC=CC3=NC2=C1 OOGYVVYCCYJADG-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 6
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000000109 phenylethoxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])O* 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 13
- 239000000203 mixture Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000126 substance Substances 0.000 description 6
- 230000001028 anti-proliverative effect Effects 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 210000004881 tumor cell Anatomy 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 235000019759 Maize starch Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
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- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
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- 241001494479 Pecora Species 0.000 description 1
- BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10035927A DE10035927A1 (de) | 2000-07-21 | 2000-07-21 | Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel |
| DE10035927.2 | 2000-07-21 | ||
| PCT/EP2001/008263 WO2002008194A1 (de) | 2000-07-21 | 2001-07-18 | Acridin-derivate und deren verwendung als arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2001289675A1 AU2001289675A1 (en) | 2002-05-02 |
| AU2001289675B2 true AU2001289675B2 (en) | 2005-04-07 |
Family
ID=7649979
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2001289675A Ceased AU2001289675B2 (en) | 2000-07-21 | 2001-07-18 | Novel heteroaryl derivatives and the use thereof as pharmaceuticals |
| AU8967501A Pending AU8967501A (en) | 2000-07-21 | 2001-07-18 | Novel heteroaryl derivatives and the use thereof as pharmaceuticals |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU8967501A Pending AU8967501A (en) | 2000-07-21 | 2001-07-18 | Novel heteroaryl derivatives and the use thereof as pharmaceuticals |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US6706722B2 (enExample) |
| EP (1) | EP1301485B1 (enExample) |
| JP (1) | JP2004504382A (enExample) |
| KR (1) | KR20030022296A (enExample) |
| CN (1) | CN1296359C (enExample) |
| AR (1) | AR033383A1 (enExample) |
| AT (1) | ATE365717T1 (enExample) |
| AU (2) | AU2001289675B2 (enExample) |
| BG (1) | BG107507A (enExample) |
| BR (1) | BR0112591A (enExample) |
| CA (1) | CA2353360A1 (enExample) |
| CY (1) | CY1106890T1 (enExample) |
| CZ (1) | CZ2003427A3 (enExample) |
| DE (2) | DE10035927A1 (enExample) |
| DK (1) | DK1301485T3 (enExample) |
| ES (1) | ES2291349T3 (enExample) |
| HU (1) | HUP0303729A3 (enExample) |
| IL (1) | IL153476A0 (enExample) |
| MX (1) | MXPA02012564A (enExample) |
| NO (1) | NO324939B1 (enExample) |
| NZ (1) | NZ524155A (enExample) |
| PL (1) | PL358808A1 (enExample) |
| PT (1) | PT1301485E (enExample) |
| RU (1) | RU2267488C2 (enExample) |
| SK (1) | SK1932003A3 (enExample) |
| UA (1) | UA75085C2 (enExample) |
| WO (1) | WO2002008194A1 (enExample) |
| ZA (1) | ZA200210411B (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10035928A1 (de) * | 2000-07-21 | 2002-03-07 | Asta Medica Ag | Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel |
| DE10037310A1 (de) * | 2000-07-28 | 2002-02-07 | Asta Medica Ag | Neue Indolderivate und deren Verwendung als Arzneimittel |
| EP1517898A1 (de) * | 2002-06-29 | 2005-03-30 | Zentaris GmbH | Aryl- und heteroarylcarbonylpiperazine und deren verwendung zur behandlung gutartiger und b sartiger tumorerkrankungen |
| MXPA05000487A (es) * | 2002-07-17 | 2005-03-23 | Zentaris Gmbh | Nuevos derivados de antraceno y su uso como un medicamento. |
| US7125461B2 (en) * | 2003-05-07 | 2006-10-24 | L & L Products, Inc. | Activatable material for sealing, baffling or reinforcing and method of forming same |
| FR2855825B1 (fr) * | 2003-06-04 | 2008-08-22 | Aventis Pharma Sa | Produits aryl-heteroaromatiques, compositions les contenant et utilisation |
| AR044586A1 (es) * | 2003-06-04 | 2005-09-21 | Aventis Pharma Sa | Productos aril - heteroaromaticos, composiciones que los contienen y su utilizacion |
| US7249415B2 (en) * | 2003-06-26 | 2007-07-31 | Zephyros, Inc. | Method of forming members for sealing or baffling |
| DE10331500A1 (de) * | 2003-07-11 | 2005-02-24 | Zentaris Gmbh | Neue Acridin-Derivate und deren Verwendung als Arzneimittel |
| EP1853594A2 (en) * | 2005-01-27 | 2007-11-14 | Alma Mater Studiorum -Universita' di Bologna | Organic compounds useful for the treatment of alzheimer's disease, their use and method of preparation |
| US20070299093A1 (en) * | 2005-01-27 | 2007-12-27 | Alma Mater Studiorum-Universitá Di Bologna | Organic Compounds Useful for the Treatment of Alzheimer's Disease, Their Use and Method of Preparation |
| WO2008106128A2 (en) * | 2007-02-26 | 2008-09-04 | Vitae Pharmaceuticals, Inc. | CYCLIC UREA AND CARBAMATE INHIBITORS OF 11β -HYDROXYSTEROID DEHYDROGENASE 1 |
| ATE554078T1 (de) * | 2007-07-26 | 2012-05-15 | Vitae Pharmaceuticals Inc | Synthese von 11-beta-hydroxysteroid-dehydrogenase-1-hemmern |
| AR069207A1 (es) * | 2007-11-07 | 2010-01-06 | Vitae Pharmaceuticals Inc | Ureas ciclicas como inhibidores de la 11 beta - hidroxi-esteroide deshidrogenasa 1 |
| EP2229368A1 (en) | 2007-12-11 | 2010-09-22 | Vitae Pharmaceuticals, Inc. | Cyclic urea inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| TW200934490A (en) * | 2008-01-07 | 2009-08-16 | Vitae Pharmaceuticals Inc | Lactam inhibitors of 11 &abgr;-hydroxysteroid dehydrogenase 1 |
| EP2252601B1 (en) * | 2008-01-24 | 2012-12-19 | Vitae Pharmaceuticals, Inc. | Cyclic carbazate and semicarbazide inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| CA2714532A1 (en) * | 2008-02-11 | 2009-08-20 | Vitae Pharmaceuticals, Inc. | 1,3-oxazepan-2-one and 1,3-diazepan-2-one inhibitors of 11.beta.-hydroxysteroid dehydrogenase 1 |
| JP5730021B2 (ja) * | 2008-02-15 | 2015-06-03 | ヴァイティー ファーマシューティカルズ，インコーポレイテッド | １１β−ヒドロキシステロイドデヒドロゲナーゼ１の阻害剤としてのシクロアルキルラクタム誘導体 |
| WO2009117109A1 (en) * | 2008-03-18 | 2009-09-24 | Vitae Pharmaceuticals, Inc. | Inhibitors of 11beta-hydroxysteroid dehydrogenase type 1 |
| WO2009134387A1 (en) | 2008-05-01 | 2009-11-05 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| JP5451752B2 (ja) * | 2008-05-01 | 2014-03-26 | ヴァイティー ファーマシューティカルズ，インコーポレイテッド | １１β−ヒドロキシステロイドデヒドロゲナーゼ１の環状インヒビター |
| WO2009134392A1 (en) | 2008-05-01 | 2009-11-05 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| NZ588954A (en) | 2008-05-01 | 2012-08-31 | Vitae Pharmaceuticals Inc | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| PL2324018T3 (pl) | 2008-07-25 | 2014-02-28 | Boehringer Ingelheim Int | Cykliczne inhibitory dehydrogenazy 11 beta-hydroksysteroidowej typu 1 |
| CA2729998A1 (en) | 2008-07-25 | 2010-01-28 | Boehringer Ingelheim International Gmbh | Inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| EP2393807B1 (en) | 2009-02-04 | 2013-08-14 | Boehringer Ingelheim International GmbH | Cyclic inhibitors of 11 -hydroxysteroid dehydrogenase 1 |
| TW201039034A (en) * | 2009-04-27 | 2010-11-01 | Chunghwa Picture Tubes Ltd | Pixel structure and the method of forming the same |
| KR20120061771A (ko) * | 2009-04-30 | 2012-06-13 | 비타이 파마슈티컬즈, 인코포레이티드 | 11베타-하이드록시스테로이드 탈수소효소 1의 고리형 억제제 |
| UA109255C2 (ru) | 2009-04-30 | 2015-08-10 | Берінгер Інгельхайм Інтернешнл Гмбх | Циклические ингибиторы 11бета-гидроксистероиддегидрогеназы 1 |
| WO2011011123A1 (en) | 2009-06-11 | 2011-01-27 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 based on the 1,3 -oxazinan- 2 -one structure |
| JP5749263B2 (ja) | 2009-07-01 | 2015-07-15 | ヴァイティー ファーマシューティカルズ，インコーポレイテッド | １１β−ヒドロキシステロイドデヒドロゲナーゼ１の環状インヒビター |
| EP2582698B1 (en) | 2010-06-16 | 2016-09-14 | Vitae Pharmaceuticals, Inc. | Substituted 5-,6- and 7-membered heterocycles, medicaments containing such compounds, and their use |
| WO2011161128A1 (en) | 2010-06-25 | 2011-12-29 | Boehringer Ingelheim International Gmbh | Azaspirohexanones as inhibitors of 11-beta-hsd1 for the treatment of metabolic disorders |
| KR20130137628A (ko) | 2010-11-02 | 2013-12-17 | 베링거 인겔하임 인터내셔날 게엠베하 | 대사 장애를 치료하기 위한 약제학적 병용물 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2538388B1 (fr) | 1982-12-24 | 1985-06-21 | Pharmuka Lab | Nouveaux derives de naphtalene- ou azanaphtalenecarboxamide, leurs procedes de preparation et leur utilisation comme medicaments |
| US4937246A (en) * | 1987-11-25 | 1990-06-26 | Takeda Chemical Industries, Ltd. | PAF antagonist, 1,4-disubstituted piperazine compounds and production thereof |
| US5030631A (en) * | 1989-11-27 | 1991-07-09 | Schering Corporation | Tricylclic arylsulfonamides |
| RU2126001C1 (ru) * | 1995-01-10 | 1999-02-10 | Самдзин Фармасьютикал Ко., Лтд | Производные пиперазина и фармацевтическая композиция на их основе |
| CZ59398A3 (cs) * | 1996-06-29 | 1998-07-15 | Samjin Pharmaceutical Co., Ltd. | Piperazinové deriváty a způsob jejich přípravy |
| US5861395A (en) | 1996-09-13 | 1999-01-19 | Schering Corporation | Compounds useful for inhibition of farnesyl proteins transferase |
| FR2753706B1 (fr) | 1996-09-20 | 1998-10-30 | Nouvelles amines cycliques n-substituees, leur procede de preparation et les compositions pharmaceutiques les renfermant | |
| DE19743435A1 (de) | 1997-10-01 | 1999-04-08 | Merck Patent Gmbh | Benzamidinderivate |
| BR9913654A (pt) | 1998-08-28 | 2001-11-27 | Scios Inc | Inibidores de p-38alfa quinase |
| JP2002538121A (ja) | 1999-03-03 | 2002-11-12 | メルク エンド カムパニー インコーポレーテッド | プレニルタンパク質トランスフェラーゼの阻害剤 |
-
2000
- 2000-07-21 DE DE10035927A patent/DE10035927A1/de not_active Withdrawn
-
2001
- 2001-07-18 MX MXPA02012564A patent/MXPA02012564A/es active IP Right Grant
- 2001-07-18 BR BR0112591-5A patent/BR0112591A/pt not_active IP Right Cessation
- 2001-07-18 AT AT01969410T patent/ATE365717T1/de not_active IP Right Cessation
- 2001-07-18 ES ES01969410T patent/ES2291349T3/es not_active Expired - Lifetime
- 2001-07-18 EP EP01969410A patent/EP1301485B1/de not_active Expired - Lifetime
- 2001-07-18 UA UA2003021451A patent/UA75085C2/uk unknown
- 2001-07-18 KR KR10-2003-7000878A patent/KR20030022296A/ko not_active Ceased
- 2001-07-18 RU RU2003105283/04A patent/RU2267488C2/ru not_active IP Right Cessation
- 2001-07-18 CN CNB018131379A patent/CN1296359C/zh not_active Expired - Fee Related
- 2001-07-18 DE DE50112669T patent/DE50112669D1/de not_active Expired - Fee Related
- 2001-07-18 SK SK193-2003A patent/SK1932003A3/sk not_active Application Discontinuation
- 2001-07-18 PL PL01358808A patent/PL358808A1/xx not_active Application Discontinuation
- 2001-07-18 HU HU0303729A patent/HUP0303729A3/hu unknown
- 2001-07-18 AU AU2001289675A patent/AU2001289675B2/en not_active Ceased
- 2001-07-18 NZ NZ524155A patent/NZ524155A/en unknown
- 2001-07-18 PT PT01969410T patent/PT1301485E/pt unknown
- 2001-07-18 IL IL15347601A patent/IL153476A0/xx unknown
- 2001-07-18 WO PCT/EP2001/008263 patent/WO2002008194A1/de not_active Ceased
- 2001-07-18 CZ CZ2003427A patent/CZ2003427A3/cs unknown
- 2001-07-18 AU AU8967501A patent/AU8967501A/xx active Pending
- 2001-07-18 JP JP2002514101A patent/JP2004504382A/ja not_active Withdrawn
- 2001-07-18 DK DK01969410T patent/DK1301485T3/da active
- 2001-07-20 US US09/910,142 patent/US6706722B2/en not_active Expired - Fee Related
- 2001-07-20 AR ARP010103480A patent/AR033383A1/es unknown
- 2001-07-20 CA CA002353360A patent/CA2353360A1/en not_active Abandoned
-
2002
- 2002-12-23 ZA ZA200210411A patent/ZA200210411B/xx unknown
-
2003
- 2003-01-20 NO NO20030301A patent/NO324939B1/no not_active IP Right Cessation
- 2003-01-30 BG BG107507A patent/BG107507A/bg unknown
-
2007
- 2007-09-26 CY CY20071101236T patent/CY1106890T1/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC1 | Assignment before grant (sect. 113) |
Owner name: ZENTARIS GMBH Free format text: FORMER APPLICANT(S): ZENTARIS AG |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |