DE10035928A1 - Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel - Google Patents
Neue Heteroaryl-Derivate und deren Verwendung als ArzneimittelInfo
- Publication number
- DE10035928A1 DE10035928A1 DE10035928A DE10035928A DE10035928A1 DE 10035928 A1 DE10035928 A1 DE 10035928A1 DE 10035928 A DE10035928 A DE 10035928A DE 10035928 A DE10035928 A DE 10035928A DE 10035928 A1 DE10035928 A1 DE 10035928A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- radical
- substituted
- mono
- 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.)
- Withdrawn
Links
- 239000003814 drug Substances 0.000 title claims abstract description 6
- 125000001072 heteroaryl group Chemical group 0.000 title claims description 8
- 229940079593 drug Drugs 0.000 title claims 2
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims abstract description 21
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract description 5
- -1 phenylethyloxy, nitro, amino Chemical group 0.000 claims description 363
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 171
- 229910052736 halogen Inorganic materials 0.000 claims description 133
- 150000002367 halogens Chemical class 0.000 claims description 133
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 72
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 72
- 229910052739 hydrogen Inorganic materials 0.000 claims description 70
- 239000001257 hydrogen Substances 0.000 claims description 70
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 68
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 68
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 63
- 125000004043 oxo group Chemical group O=* 0.000 claims description 60
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims description 58
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 58
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 56
- 229910052731 fluorine Inorganic materials 0.000 claims description 49
- 239000011737 fluorine Substances 0.000 claims description 49
- 125000003282 alkyl amino group Chemical group 0.000 claims description 27
- 150000003248 quinolines Chemical class 0.000 claims description 26
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 20
- 125000001153 fluoro group Chemical group F* 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 12
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 4
- 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
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 4
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 3
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 3
- 125000004941 pyridazin-5-yl group Chemical group N1=NC=CC(=C1)* 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
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 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
- RPBWZBPLNQWXMX-UHFFFAOYSA-N [C].N1=CC=CC2=CC=CC=C21 Chemical group [C].N1=CC=CC2=CC=CC=C21 RPBWZBPLNQWXMX-UHFFFAOYSA-N 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 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
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 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
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-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
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 13
- 239000000203 mixture Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 4
- 239000004480 active ingredient Substances 0.000 description 4
- 230000001028 anti-proliverative effect Effects 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
- 239000007787 solid Substances 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
- 239000002775 capsule Substances 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
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000003958 fumigation Methods 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000001464 adherent effect Effects 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 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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- 230000005764 inhibitory process Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
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- VQMSRUREDGBWKT-UHFFFAOYSA-N quinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=NC2=C1 VQMSRUREDGBWKT-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
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- COWMQOCYJSUFSB-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)piperazine Chemical compound COC1=CC(OC)=CC(N2CCNCC2)=C1 COWMQOCYJSUFSB-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- IYNDUQTYGRPHHW-UHFFFAOYSA-N 4-methoxy-2-nitrobenzenesulfonic acid Chemical compound COC1=CC=C(S(O)(=O)=O)C([N+]([O-])=O)=C1 IYNDUQTYGRPHHW-UHFFFAOYSA-N 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (28)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10035928A DE10035928A1 (de) | 2000-07-21 | 2000-07-21 | Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel |
| MXPA02012565A MXPA02012565A (es) | 2000-07-21 | 2001-07-18 | Nuevos derivados de heteroarilo y el uso de estos como medicamentos. |
| KR10-2003-7000707A KR20030022287A (ko) | 2000-07-21 | 2001-07-18 | 신규한 헤테로아릴 유도체 및 약제로서 이의 용도 |
| BR0112589-3A BR0112589A (pt) | 2000-07-21 | 2001-07-18 | Derivados de heteroarila e sua aplicação como medicamento |
| IL15336101A IL153361A0 (en) | 2000-07-21 | 2001-07-18 | Novel heteroaryl derivatives and the use thereof as pharmaceuticals |
| CZ2003415A CZ2003415A3 (cs) | 2000-07-21 | 2001-07-18 | Nové heteroarylové deriváty a jejich použití jako léčiv |
| AU7975701A AU7975701A (en) | 2000-07-21 | 2001-07-18 | Novel heteroaryl derivatives and the use thereof as pharmaceuticals |
| RU2003105278/04A RU2265602C2 (ru) | 2000-07-21 | 2001-07-18 | Производные хинолина, способ их получения и их применение, лекарственное средство и способ ингибирования пролиферации опухолевых клеток |
| AU2001279757A AU2001279757B2 (en) | 2000-07-21 | 2001-07-18 | Novel heteroaryl derivatives and the use thereof as pharmaceuticals |
| HU0300838A HUP0300838A2 (hu) | 2000-07-21 | 2001-07-18 | Új heteroarilszármazékok, eljárás az előállításukra és gyógyszerként való alkalmazásuk |
| EP01957978A EP1305290A1 (de) | 2000-07-21 | 2001-07-18 | Neue heteroaryl-derivate und deren verwendung als arzneimittel |
| JP2002514099A JP2004504381A (ja) | 2000-07-21 | 2001-07-18 | 新規のヘテロアリール誘導体および医薬としてのその使用 |
| PL01358788A PL358788A1 (en) | 2000-07-21 | 2001-07-18 | Novel heteroaryl derivatives and the use thereof as pharmaceuticals |
| SK1842003A SK1842003A3 (en) | 2000-07-21 | 2001-07-18 | Novel heteroaryl derivatives and the use thereof as pharmaceuticals |
| PCT/EP2001/008261 WO2002008192A1 (de) | 2000-07-21 | 2001-07-18 | Neue heteroaryl-derivate und deren verwendung als arzneimittel |
| CN01813158A CN1443171A (zh) | 2000-07-21 | 2001-07-18 | 新的杂芳基衍生物及其作为药物的应用 |
| NZ524154A NZ524154A (en) | 2000-07-21 | 2001-07-18 | Novel heteroaryl derivatives and the use thereof as pharmaceuticals |
| ARP010103481A AR033678A1 (es) | 2000-07-21 | 2001-07-20 | Derivados de quinolina, procedimiento para prepararlos, uso de los mismos para la preparacion de medicamentos y los medicamentos que contienen dichos derivados |
| CA002353369A CA2353369A1 (en) | 2000-07-21 | 2001-07-20 | Novel heteroaryl derivatives and their use as medicaments |
| US09/910,141 US6890926B2 (en) | 2000-07-21 | 2001-07-20 | Heteroaryl derivatives and their use as medicaments |
| TW090117947A TWI228505B (en) | 2000-07-21 | 2001-07-23 | Novel heteroaryl derivatives and their use as medicaments |
| ZA200210180A ZA200210180B (en) | 2000-07-21 | 2002-12-17 | Novel heteroaryl derivatives and the use thereof as pharmaceuticals. |
| NO20030298A NO20030298L (no) | 2000-07-21 | 2003-01-20 | Nye heteroarylderivater og deres anvendelse som farmasöytiske midler |
| BG107508A BG107508A (bg) | 2000-07-21 | 2003-01-30 | Нови хетероарилови производни и тяхното използване като лекарствени средства |
| US10/713,859 US7056912B2 (en) | 2000-07-21 | 2003-11-14 | Heteroaryl derivatives and their use as medicaments |
| US10/741,310 US6936615B2 (en) | 2000-07-21 | 2003-12-19 | Heteroaryl derivatives and their use as medicaments |
| US11/105,622 US7026310B2 (en) | 2000-07-21 | 2005-04-14 | Heteroaryl derivatives and their use as medicaments |
| US11/152,599 US20050245523A1 (en) | 2000-07-21 | 2005-06-14 | Heteroaryl derivatives and their use as medicaments |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10035928A DE10035928A1 (de) | 2000-07-21 | 2000-07-21 | Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10035928A1 true DE10035928A1 (de) | 2002-03-07 |
Family
ID=7649980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10035928A Withdrawn DE10035928A1 (de) | 2000-07-21 | 2000-07-21 | Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel |
Country Status (23)
| Country | Link |
|---|---|
| US (5) | US6890926B2 (https=) |
| EP (1) | EP1305290A1 (https=) |
| JP (1) | JP2004504381A (https=) |
| KR (1) | KR20030022287A (https=) |
| CN (1) | CN1443171A (https=) |
| AR (1) | AR033678A1 (https=) |
| AU (2) | AU7975701A (https=) |
| BG (1) | BG107508A (https=) |
| BR (1) | BR0112589A (https=) |
| CA (1) | CA2353369A1 (https=) |
| CZ (1) | CZ2003415A3 (https=) |
| DE (1) | DE10035928A1 (https=) |
| HU (1) | HUP0300838A2 (https=) |
| IL (1) | IL153361A0 (https=) |
| MX (1) | MXPA02012565A (https=) |
| NO (1) | NO20030298L (https=) |
| NZ (1) | NZ524154A (https=) |
| PL (1) | PL358788A1 (https=) |
| RU (1) | RU2265602C2 (https=) |
| SK (1) | SK1842003A3 (https=) |
| TW (1) | TWI228505B (https=) |
| WO (1) | WO2002008192A1 (https=) |
| ZA (1) | ZA200210180B (https=) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA79286C2 (en) * | 2002-06-29 | 2007-06-11 | Zentaris Gmbh | Arylcarbonylpipererazines and heteroarylcarbonylpiperazines and their use in the treatment of benign and malignant tumors |
| EP1521748A1 (de) * | 2002-07-17 | 2005-04-13 | Zentaris GmbH | Neue anthracen-derivate und deren verwendung als arzneimittel |
| BRPI0407088A (pt) * | 2003-01-28 | 2006-01-24 | Aventis Pharma Sa | Produtos n-aril-heteroaromáticos, composições contendo os mesmos e seu uso |
| PE20050226A1 (es) * | 2003-06-04 | 2005-05-18 | Aventis Pharma Sa | Productos aril-heteroaromaticos y composiciones que los contienen |
| FR2855825B1 (fr) * | 2003-06-04 | 2008-08-22 | Aventis Pharma Sa | Produits aryl-heteroaromatiques, compositions les contenant et utilisation |
| US7723362B2 (en) * | 2004-01-08 | 2010-05-25 | Syngenta Crop Protection, Inc. | Pesticidal heterocyclic dihaloallyl compounds |
| DE102004003428A1 (de) * | 2004-01-23 | 2005-08-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue langwirksame Beta-2-Agonisten, und deren Verwendung als Arzneimittel |
| FR2871157A1 (fr) * | 2004-06-04 | 2005-12-09 | Aventis Pharma Sa | Produits biaryl aromatiques, compositions les contenant et utilisation |
| CN1830964B (zh) * | 2005-03-11 | 2011-06-15 | 中国科学院上海药物研究所 | 4-取代苯氨基-3-硝基喹啉类化合物及其制备方法和用途 |
| KR101139413B1 (ko) * | 2006-12-07 | 2012-06-22 | 차이나 메디컬 유니버시티 | 항암제로서 새로운 2-아릴-4-퀴놀론의 친수성 유도체 |
| CA2678577A1 (en) * | 2007-02-26 | 2008-09-04 | Vitae Pharmaceuticals, Inc. | Cyclic urea and carbamate inhibitors of 11.beta.-hydroxysteroid dehydrogenase 1 |
| JP5470557B2 (ja) * | 2007-07-26 | 2014-04-16 | 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型の阻害剤の合成 |
| AR069207A1 (es) * | 2007-11-07 | 2010-01-06 | Vitae Pharmaceuticals Inc | Ureas ciclicas como inhibidores de la 11 beta - hidroxi-esteroide deshidrogenasa 1 |
| US8440658B2 (en) | 2007-12-11 | 2013-05-14 | Vitae Pharmaceuticals, Inc. | Cyclic urea inhibitors of 11β-hydroxysteroid dehydrogenase 1 |
| TW200934490A (en) * | 2008-01-07 | 2009-08-16 | Vitae Pharmaceuticals Inc | Lactam inhibitors of 11 &abgr;-hydroxysteroid dehydrogenase 1 |
| WO2009094169A1 (en) * | 2008-01-24 | 2009-07-30 | 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 |
| US8598160B2 (en) * | 2008-02-15 | 2013-12-03 | Vitae Pharmaceuticals, Inc. | Cycloalkyl lactame derivatives as inhibitors of 11-beta-hydroxysteroid dehydrogenase 1 |
| WO2009117109A1 (en) * | 2008-03-18 | 2009-09-24 | Vitae Pharmaceuticals, Inc. | Inhibitors of 11beta-hydroxysteroid dehydrogenase type 1 |
| RU2531272C2 (ru) | 2008-05-01 | 2014-10-20 | Вайтаи Фармасьютиклз, Инк. | Циклические ингибиторы 11бета-гидроксистероид-дегидрогеназы 1 |
| US8242111B2 (en) * | 2008-05-01 | 2012-08-14 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1 |
| EP2291370B1 (en) | 2008-05-01 | 2013-11-27 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| JP5696037B2 (ja) | 2008-05-01 | 2015-04-08 | 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 |
| WO2010010157A2 (en) | 2008-07-25 | 2010-01-28 | Boehringer Ingelheim International Gmbh | INHIBITORS OF 11beta-HYDROXYSTEROID DEHYDROGENASE 1 |
| NZ590495A (en) | 2008-07-25 | 2012-10-26 | Vitae Pharmaceuticals Inc | Dihydropyridin-phenyl-3-oxazinan-2-ones as inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| JP5679997B2 (ja) | 2009-02-04 | 2015-03-04 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | １１β−ヒドロキシステロイドデヒドロゲナーゼ１の環状阻害剤 |
| TW201039034A (en) * | 2009-04-27 | 2010-11-01 | Chunghwa Picture Tubes Ltd | Pixel structure and the method of forming the same |
| GEP20156309B (en) * | 2009-04-30 | 2015-07-10 | Vitae Pharmaceuticals Inc | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| US8680093B2 (en) | 2009-04-30 | 2014-03-25 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| US8927539B2 (en) | 2009-06-11 | 2015-01-06 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1 based on the 1,3-oxazinan-2-one structure |
| EP2448928B1 (en) | 2009-07-01 | 2014-08-13 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| WO2011159760A1 (en) | 2010-06-16 | 2011-12-22 | 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 |
| WO2012059416A1 (en) | 2010-11-02 | 2012-05-10 | Boehringer Ingelheim International Gmbh | Pharmaceutical combinations for the treatment of metabolic disorders |
| US11084807B2 (en) | 2016-08-18 | 2021-08-10 | Vidac Pharama Ltd. | Piperazine derivatives, pharmaceutical compositions and methods of use thereof |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR79603B (https=) * | 1982-07-24 | 1984-10-31 | Pfizer | |
| 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 |
| EP0318235A3 (en) * | 1987-11-25 | 1991-05-02 | Takeda Chemical Industries, Ltd. | Paf antagonist, 1,4-disubstituted piperazine compounds and production thereof |
| KR970005927B1 (ko) | 1990-10-10 | 1997-04-22 | 쉐링 코포레이션 | 디아릴메틸피페리딘 또는 피페라진의 피리딘 및 피리딘 n-옥사이드 유도체, 이를 함유하는 약제학적 조성물 및 이의 제조방법 |
| WO1995000497A1 (en) * | 1993-06-18 | 1995-01-05 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| CZ296163B6 (cs) * | 1996-05-20 | 2006-01-11 | Karboxyamidy chinolinu jako inhibitory TNF a inhibitory PDE-IV | |
| US6686353B1 (en) | 1996-05-20 | 2004-02-03 | Teijin Intellectual Property Center Limited | Diarylalkyl cyclic diamine derivatives as chemokine receptor antagonists |
| SK27598A3 (en) * | 1996-06-29 | 1998-11-04 | Samjin Pharm Co Ltd | Piperazine derivatives and process for the preparation thereof |
| 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 | |
| KR100538152B1 (ko) * | 1997-07-07 | 2005-12-21 | 코와 가부시키가이샤 | 디아민 유도체 및 이를 함유하는 의약 |
| DE19743435A1 (de) | 1997-10-01 | 1999-04-08 | Merck Patent Gmbh | Benzamidinderivate |
| MXPA01002173A (es) * | 1998-08-28 | 2003-07-14 | Scios Inc | Inhibidores de p38-alfa cinasa. |
| AU3248600A (en) | 1999-03-03 | 2000-09-21 | Merck & Co., Inc. | Inhibitors of prenyl-protein transferases |
| DE10035927A1 (de) * | 2000-07-21 | 2002-03-07 | Asta Medica Ag | Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel |
| US6610274B1 (en) * | 2000-12-22 | 2003-08-26 | Wallace J. Gardner | Anti-inflammatory composition comprising tetracycline |
-
2000
- 2000-07-21 DE DE10035928A patent/DE10035928A1/de not_active Withdrawn
-
2001
- 2001-07-18 AU AU7975701A patent/AU7975701A/xx active Pending
- 2001-07-18 PL PL01358788A patent/PL358788A1/xx not_active Application Discontinuation
- 2001-07-18 HU HU0300838A patent/HUP0300838A2/hu unknown
- 2001-07-18 EP EP01957978A patent/EP1305290A1/de not_active Withdrawn
- 2001-07-18 NZ NZ524154A patent/NZ524154A/en unknown
- 2001-07-18 WO PCT/EP2001/008261 patent/WO2002008192A1/de not_active Ceased
- 2001-07-18 JP JP2002514099A patent/JP2004504381A/ja active Pending
- 2001-07-18 CN CN01813158A patent/CN1443171A/zh active Pending
- 2001-07-18 BR BR0112589-3A patent/BR0112589A/pt not_active IP Right Cessation
- 2001-07-18 AU AU2001279757A patent/AU2001279757B2/en not_active Ceased
- 2001-07-18 RU RU2003105278/04A patent/RU2265602C2/ru not_active IP Right Cessation
- 2001-07-18 IL IL15336101A patent/IL153361A0/xx unknown
- 2001-07-18 KR KR10-2003-7000707A patent/KR20030022287A/ko not_active Withdrawn
- 2001-07-18 CZ CZ2003415A patent/CZ2003415A3/cs unknown
- 2001-07-18 MX MXPA02012565A patent/MXPA02012565A/es unknown
- 2001-07-18 SK SK1842003A patent/SK1842003A3/sk not_active Application Discontinuation
- 2001-07-20 US US09/910,141 patent/US6890926B2/en not_active Expired - Fee Related
- 2001-07-20 CA CA002353369A patent/CA2353369A1/en not_active Abandoned
- 2001-07-20 AR ARP010103481A patent/AR033678A1/es not_active Application Discontinuation
- 2001-07-23 TW TW090117947A patent/TWI228505B/zh not_active IP Right Cessation
-
2002
- 2002-12-17 ZA ZA200210180A patent/ZA200210180B/xx unknown
-
2003
- 2003-01-20 NO NO20030298A patent/NO20030298L/no unknown
- 2003-01-30 BG BG107508A patent/BG107508A/bg unknown
- 2003-11-14 US US10/713,859 patent/US7056912B2/en not_active Expired - Fee Related
- 2003-12-19 US US10/741,310 patent/US6936615B2/en not_active Expired - Fee Related
-
2005
- 2005-04-14 US US11/105,622 patent/US7026310B2/en not_active Expired - Fee Related
- 2005-06-14 US US11/152,599 patent/US20050245523A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0300838A2 (hu) | 2003-07-28 |
| US6890926B2 (en) | 2005-05-10 |
| PL358788A1 (en) | 2004-08-23 |
| MXPA02012565A (es) | 2003-09-22 |
| NZ524154A (en) | 2005-02-25 |
| BR0112589A (pt) | 2003-05-20 |
| JP2004504381A (ja) | 2004-02-12 |
| NO20030298D0 (no) | 2003-01-20 |
| WO2002008192A1 (de) | 2002-01-31 |
| AU2001279757B2 (en) | 2005-05-26 |
| CA2353369A1 (en) | 2002-01-21 |
| IL153361A0 (en) | 2003-07-06 |
| CZ2003415A3 (cs) | 2004-05-12 |
| CN1443171A (zh) | 2003-09-17 |
| US7026310B2 (en) | 2006-04-11 |
| US20050176744A1 (en) | 2005-08-11 |
| US20040132747A1 (en) | 2004-07-08 |
| US20040097530A1 (en) | 2004-05-20 |
| TWI228505B (en) | 2005-03-01 |
| SK1842003A3 (en) | 2004-10-05 |
| RU2265602C2 (ru) | 2005-12-10 |
| EP1305290A1 (de) | 2003-05-02 |
| BG107508A (bg) | 2003-09-30 |
| US6936615B2 (en) | 2005-08-30 |
| US20020103214A1 (en) | 2002-08-01 |
| ZA200210180B (en) | 2003-02-12 |
| NO20030298L (no) | 2003-01-20 |
| AU7975701A (en) | 2002-02-05 |
| KR20030022287A (ko) | 2003-03-15 |
| US7056912B2 (en) | 2006-06-06 |
| AR033678A1 (es) | 2004-01-07 |
| US20050245523A1 (en) | 2005-11-03 |
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