CZ2003415A3 - Nové heteroarylové deriváty a jejich použití jako léčiv - Google Patents
Nové heteroarylové deriváty a jejich použití jako léčiv Download PDFInfo
- Publication number
- CZ2003415A3 CZ2003415A3 CZ2003415A CZ2003415A CZ2003415A3 CZ 2003415 A3 CZ2003415 A3 CZ 2003415A3 CZ 2003415 A CZ2003415 A CZ 2003415A CZ 2003415 A CZ2003415 A CZ 2003415A CZ 2003415 A3 CZ2003415 A3 CZ 2003415A3
- Authority
- CZ
- Czechia
- Prior art keywords
- alkyl
- substituted
- radical
- alkylamino
- aryl
- Prior art date
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- 125000001072 heteroaryl group Chemical group 0.000 title claims abstract description 15
- 239000003814 drug Substances 0.000 title claims abstract description 10
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- -1 alkyl quinoline Chemical compound 0.000 claims description 315
- 125000000217 alkyl group Chemical group 0.000 claims description 162
- 229910052736 halogen Inorganic materials 0.000 claims description 106
- 150000002367 halogens Chemical class 0.000 claims description 103
- 125000003282 alkyl amino group Chemical group 0.000 claims description 90
- 125000003118 aryl group Chemical group 0.000 claims description 76
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 72
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 71
- 229910052739 hydrogen Inorganic materials 0.000 claims description 63
- 239000001257 hydrogen Substances 0.000 claims description 63
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 61
- 125000001153 fluoro group Chemical group F* 0.000 claims description 61
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 52
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 44
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 39
- 125000003545 alkoxy group Chemical group 0.000 claims description 38
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 33
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 31
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 27
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 26
- 150000003254 radicals Chemical class 0.000 claims description 25
- 150000003248 quinolines Chemical class 0.000 claims description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 19
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 125000004043 oxo group Chemical group O=* 0.000 claims description 16
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 6
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 6
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 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
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 241001611408 Nebo Species 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
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 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
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims 3
- 150000003852 triazoles Chemical class 0.000 claims 2
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims 1
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- CSJDCSCTVDEHRN-UHFFFAOYSA-N methane;molecular oxygen Chemical group C.O=O CSJDCSCTVDEHRN-UHFFFAOYSA-N 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims 1
- 125000004941 pyridazin-5-yl group Chemical group N1=NC=CC(=C1)* 0.000 claims 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims 1
- 150000003536 tetrazoles Chemical class 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 12
- 239000000203 mixture Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 6
- 238000003556 assay Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 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
- 239000013543 active substance Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 150000002431 hydrogen Chemical class 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
- 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
- 230000001413 cellular effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 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
- 238000002474 experimental method Methods 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 101710088194 Dehydrogenase Proteins 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
- 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
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-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
- 230000001028 anti-proliverative effect Effects 0.000 description 2
- 201000011510 cancer Diseases 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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- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
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- 125000006530 (C4-C6) alkyl group Chemical group 0.000 description 1
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- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 208000036832 Adenocarcinoma of ovary Diseases 0.000 description 1
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
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- 235000008476 powdered milk Nutrition 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- VQMSRUREDGBWKT-UHFFFAOYSA-N quinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=NC2=C1 VQMSRUREDGBWKT-UHFFFAOYSA-N 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 102000012498 secondary active transmembrane transporter activity proteins Human genes 0.000 description 1
- 108040003878 secondary active transmembrane transporter activity proteins Proteins 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- BCVUXOUXNFPURU-UHFFFAOYSA-M sodium 4-methoxy-2-nitrobenzenesulfonate Chemical compound [Na+].COc1ccc(c(c1)[N+]([O-])=O)S([O-])(=O)=O BCVUXOUXNFPURU-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 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)
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 |
|---|---|
| CZ2003415A3 true CZ2003415A3 (cs) | 2004-05-12 |
Family
ID=7649980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ2003415A CZ2003415A3 (cs) | 2000-07-21 | 2001-07-18 | Nové heteroarylové deriváty a jejich použití jako léčiv |
Country Status (23)
| Country | Link |
|---|---|
| US (5) | US6890926B2 (enExample) |
| EP (1) | EP1305290A1 (enExample) |
| JP (1) | JP2004504381A (enExample) |
| KR (1) | KR20030022287A (enExample) |
| CN (1) | CN1443171A (enExample) |
| AR (1) | AR033678A1 (enExample) |
| AU (2) | AU7975701A (enExample) |
| BG (1) | BG107508A (enExample) |
| BR (1) | BR0112589A (enExample) |
| CA (1) | CA2353369A1 (enExample) |
| CZ (1) | CZ2003415A3 (enExample) |
| DE (1) | DE10035928A1 (enExample) |
| HU (1) | HUP0300838A2 (enExample) |
| IL (1) | IL153361A0 (enExample) |
| MX (1) | MXPA02012565A (enExample) |
| NO (1) | NO20030298L (enExample) |
| NZ (1) | NZ524154A (enExample) |
| PL (1) | PL358788A1 (enExample) |
| RU (1) | RU2265602C2 (enExample) |
| SK (1) | SK1842003A3 (enExample) |
| TW (1) | TWI228505B (enExample) |
| WO (1) | WO2002008192A1 (enExample) |
| ZA (1) | ZA200210180B (enExample) |
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 (enExample) * | 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 |
| DE10035928A1 (de) | 2002-03-07 |
| 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 |
| 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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