HRP20020072A2 - Carboxylic acid amides, medicaments containing these compounds and the use and production thereof - Google Patents
Carboxylic acid amides, medicaments containing these compounds and the use and production thereof Download PDFInfo
- Publication number
- HRP20020072A2 HRP20020072A2 HR20020072A HRP20020072A HRP20020072A2 HR P20020072 A2 HRP20020072 A2 HR P20020072A2 HR 20020072 A HR20020072 A HR 20020072A HR P20020072 A HRP20020072 A HR P20020072A HR P20020072 A2 HRP20020072 A2 HR P20020072A2
- Authority
- HR
- Croatia
- Prior art keywords
- group
- phenyl
- alkyl
- substituted
- trans
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 54
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000003814 drug Substances 0.000 title description 2
- -1 monosubstituted phenyl Chemical group 0.000 claims description 236
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 174
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 148
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 106
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 90
- 229910052801 chlorine Inorganic materials 0.000 claims description 77
- 229910052731 fluorine Inorganic materials 0.000 claims description 76
- 239000000460 chlorine Chemical group 0.000 claims description 75
- 239000011737 fluorine Chemical group 0.000 claims description 72
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 67
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 58
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 58
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 49
- 125000001624 naphthyl group Chemical group 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 38
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 35
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 35
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 28
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 26
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 25
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 239000001301 oxygen Substances 0.000 claims description 24
- 229910052717 sulfur Chemical group 0.000 claims description 24
- 125000004434 sulfur atom Chemical group 0.000 claims description 24
- 229910052794 bromium Inorganic materials 0.000 claims description 23
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 21
- 108010017842 Telomerase Proteins 0.000 claims description 21
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 21
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 20
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 20
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 19
- 238000001727 in vivo Methods 0.000 claims description 19
- 229910052740 iodine Inorganic materials 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000001153 fluoro group Chemical group F* 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 16
- 125000002950 monocyclic group Chemical group 0.000 claims description 16
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 15
- 125000002883 imidazolyl group Chemical group 0.000 claims description 14
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 14
- 150000001408 amides Chemical class 0.000 claims description 13
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims description 12
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 12
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 12
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical group C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 claims description 12
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 10
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 150000001735 carboxylic acids Chemical class 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 9
- 125000006563 (C1-3) alkylaminocarbonyl group Chemical group 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 7
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 7
- 125000006593 (C2-C3) alkynyl group Chemical group 0.000 claims description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- 230000004962 physiological condition Effects 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 125000006603 (C1-C3) alkylaminosulfonyl group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000005047 dihydroimidazolyl group Chemical group N1(CNC=C1)* 0.000 claims description 6
- 125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 claims description 6
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- 230000010933 acylation Effects 0.000 claims description 5
- 238000005917 acylation reaction Methods 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 4
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 4
- QXPDUSOCUWYROV-UHFFFAOYSA-N 4-(2-piperidin-1-yl-2-pyrrolidin-1-ylpiperazin-1-yl)morpholine Chemical compound C1CCCN1C1(N2CCCCC2)N(N2CCOCC2)CCNC1 QXPDUSOCUWYROV-UHFFFAOYSA-N 0.000 claims description 4
- SEZWJRWTCIPRSV-UHFFFAOYSA-N [N]C(N)=O Chemical group [N]C(N)=O SEZWJRWTCIPRSV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 4
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 4
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 230000006103 sulfonylation Effects 0.000 claims description 4
- 238000005694 sulfonylation reaction Methods 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 229940002612 prodrug Drugs 0.000 claims description 3
- 239000000651 prodrug Substances 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
- 150000003461 sulfonyl halides Chemical class 0.000 claims description 2
- 125000001680 trimethoxyphenyl group Chemical group 0.000 claims description 2
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 claims 9
- 239000000969 carrier Substances 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 891
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 753
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 372
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 357
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 255
- 239000000741 silica gel Substances 0.000 description 253
- 229910002027 silica gel Inorganic materials 0.000 description 253
- 238000001819 mass spectrum Methods 0.000 description 246
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 175
- 239000000243 solution Substances 0.000 description 159
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 156
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 97
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 96
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 87
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 76
- 239000011734 sodium Substances 0.000 description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
- 229940086542 triethylamine Drugs 0.000 description 52
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- FPQMGQZTBWIHDN-UHFFFAOYSA-N 5-fluoroanthranilic acid Chemical compound NC1=CC=C(F)C=C1C(O)=O FPQMGQZTBWIHDN-UHFFFAOYSA-N 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 19
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
- 239000003208 petroleum Substances 0.000 description 14
- 229960000583 acetic acid Drugs 0.000 description 13
- 210000004027 cell Anatomy 0.000 description 13
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
- 239000013543 active substance Substances 0.000 description 12
- 239000000284 extract Substances 0.000 description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 11
- 206010028980 Neoplasm Diseases 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 108020004414 DNA Proteins 0.000 description 8
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 8
- 235000019359 magnesium stearate Nutrition 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 229920002261 Corn starch Polymers 0.000 description 7
- 239000000872 buffer Substances 0.000 description 7
- 239000008120 corn starch Substances 0.000 description 7
- 229940099112 cornstarch Drugs 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- 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 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 5
- 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 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
- 102000006382 Ribonucleases Human genes 0.000 description 5
- 108010083644 Ribonucleases Proteins 0.000 description 5
- VHJLVAABSRFDPM-ZXZARUISSA-N dithioerythritol Chemical compound SC[C@H](O)[C@H](O)CS VHJLVAABSRFDPM-ZXZARUISSA-N 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 150000007530 organic bases Chemical class 0.000 description 5
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 5
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
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Classifications
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
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- C07C233/55—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a carbon atom of an unsaturated carbon skeleton
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- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
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- C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
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- C07C255/00—Carboxylic acid nitriles
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- C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
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- C07C309/63—Esters of sulfonic acids
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US6645964B1 (en) * | 1999-11-29 | 2003-11-11 | Aventis Pharma S.A. | Chemical derivatives and their application as antitelomerase agent |
US20040043904A1 (en) * | 2000-09-22 | 2004-03-04 | Hiroshi Yamaguchi | N-(4-pyrazolyl) amide derivatives, chemicals for agricultural and horticultural use, and usage of the same |
DE10065042A1 (de) * | 2000-12-23 | 2002-06-27 | Boehringer Ingelheim Pharma | Carbonsäureamide, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Herstellung |
US6887873B2 (en) | 2001-03-23 | 2005-05-03 | Aventis Pharma S.A. | Triazine derivatives and their application as antitelomerase agents |
CA2441274A1 (en) * | 2001-04-18 | 2002-10-24 | Pharmacia Italia S.P.A. | Aurones as telomerase inhibitors |
AU2002314252A1 (en) * | 2001-05-28 | 2002-12-09 | Aventis Pharma S.A. | Chemical derivatives and the use thereof as an anti-telomerase agent |
FR2825090B1 (fr) * | 2001-05-28 | 2003-08-01 | Aventis Pharma Sa | Derives chimiques et leur application comme agent antitelomerase |
GB0127615D0 (en) * | 2001-07-09 | 2002-01-09 | Aventis Pharm Prod Inc | Substituted amides, sulfonamides and ureas useful for inhibiting kinase activity |
JP2005518371A (ja) * | 2001-12-10 | 2005-06-23 | アムジエン・インコーポレーテツド | バニロイド受容体リガンド及び治療に於けるこれらの使用 |
US20070232572A1 (en) * | 2003-02-07 | 2007-10-04 | Aventis Pharma S.A. | Chemical derivatives as antitelomerase agents which bind specifically to the G-quadruplex DNA structures and their application as a specific anticancer agent |
JP2006520759A (ja) * | 2003-03-21 | 2006-09-14 | ハー・ルンドベック・アクチエゼルスカベット | 置換されたp−ジアミノベンゼン誘導体 |
GB0316546D0 (en) * | 2003-07-15 | 2003-08-20 | Novartis Ag | Process for the manufacture of organic compounds |
AU2005286701A1 (en) * | 2004-09-21 | 2006-03-30 | Synta Pharmaceutical Corp. | Compounds for inflammation and immune-related uses |
US8084492B2 (en) * | 2004-11-19 | 2011-12-27 | The New Industry Research Organization | Benzofuran compound and pharmaceutical composition containing the same |
US20070072873A1 (en) * | 2005-09-27 | 2007-03-29 | Henrietta Dehmlow | Novel thiophene derivatives which are HM74A agonists |
MX352516B (es) | 2006-07-05 | 2017-04-06 | Fibrotech Therapeutics Pty Ltd | Compuestos terapeuticos. |
EP2076122A4 (en) | 2007-06-29 | 2011-06-22 | Acucela Inc | ALKYNYLPHENYL DERIVATIVES FOR TREATING OPHTHALMIC DISEASES AND DISORDERS |
EP2172454A4 (en) | 2007-07-24 | 2010-12-08 | Astellas Pharma Inc | benzimidazole derivative |
WO2009079692A1 (en) * | 2007-12-21 | 2009-07-02 | Fibrotech Therapeutics Pty Ltd | Halogenated analogues of anti-fibrotic agents |
WO2009100323A2 (en) * | 2008-02-08 | 2009-08-13 | Grand Valley State University | Methods of using carboxylic amides as antimicrobial agents |
WO2010087319A1 (ja) | 2009-01-27 | 2010-08-05 | アステラス製薬株式会社 | 前立腺癌治療剤として有効な物質のスクリーニング方法 |
WO2010144959A1 (en) * | 2009-06-18 | 2010-12-23 | Fibrotech Therapeutics Pty Ltd | Analogues of anti-fibrotic agents |
CN102574843B (zh) | 2009-10-22 | 2015-06-17 | 法博太科制药有限公司 | 抗纤维化剂的稠环类似物 |
EP2758041B1 (de) | 2011-09-20 | 2021-01-13 | Basf Se | Niedermolekulare modulatoren des kälte-menthol-rezeptors trpm8 und deren verwendung |
JP5957537B2 (ja) * | 2011-12-21 | 2016-07-27 | ビオタ ヨーロッパ リミテッドBiota Europe Ltd | 複素環式ウレア化合物 |
CN110546133A (zh) | 2017-02-03 | 2019-12-06 | 塞尔塔治疗有限公司 | 抗纤维化化合物 |
CN110357789B (zh) * | 2018-04-11 | 2022-09-30 | 华东理工大学 | 作为dhodh抑制剂的n-取代丙烯酰胺衍生物及其制备和用途 |
CN114831977B (zh) * | 2021-02-02 | 2023-12-19 | 北京大学 | 苯甲酸类衍生物作为trpm2蛋白抑制剂的用途 |
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JPS5640710B2 (es) * | 1973-01-18 | 1981-09-22 | ||
JPS5848545B2 (ja) * | 1974-04-18 | 1983-10-28 | キツセイヤクヒンコウギヨウ カブシキガイシヤ | シンキホウコウゾクカルボンサンアミドユウドウタイ ノ セイゾウホウホウ |
JPS6097946A (ja) * | 1983-11-01 | 1985-05-31 | Ono Pharmaceut Co Ltd | カルボキサミド誘導体 |
JPS60139646A (ja) * | 1983-12-27 | 1985-07-24 | Otsuka Pharmaceut Factory Inc | ナフタレン誘導体 |
JPS60146855A (ja) * | 1984-01-11 | 1985-08-02 | Ono Pharmaceut Co Ltd | アニリン誘導体 |
JPS61170528A (ja) | 1985-01-22 | 1986-08-01 | Sutaaroi Sangyo Kk | コバルトの剥離回収方法 |
CA2062587A1 (en) * | 1991-03-11 | 1992-09-12 | Toshiaki Kumazawa | Indole derivatives |
JPH0578315A (ja) * | 1991-03-11 | 1993-03-30 | Kyowa Hakko Kogyo Co Ltd | インドール誘導体 |
JPH0672866A (ja) * | 1992-07-02 | 1994-03-15 | Chugoku Igakuka Gakuin Yakubutsu Kenkyusho | 分化誘導剤 |
IT1276462B1 (it) | 1995-07-03 | 1997-10-31 | Rotta Research Lab | Diamidi aromatiche acide ad attivita' antigastrinica, procedimento per la loro preparazione e loro uso farmaceutico |
JPH09154575A (ja) * | 1995-10-04 | 1997-06-17 | Soosei:Kk | テロメラーゼ |
IT1286141B1 (it) | 1996-07-02 | 1998-07-07 | Rotta Research Lab | Derivati diammidici dell'acido antranilico ad attivita' antigastrinica procedimento per la loro preparazione e loro uso farmaceutico. |
FR2759368B1 (fr) | 1997-02-10 | 2001-06-01 | Galderma Rech Dermatologique | Composes biaromatiques, compositions les contenant et utilisations |
JPH1149676A (ja) * | 1997-07-31 | 1999-02-23 | Geron Corp | ピリジン系テロメラーゼ阻害剤 |
WO1999007669A1 (en) * | 1997-08-05 | 1999-02-18 | American Home Products Corporation | Anthranilic acid analogs |
DE69824885T2 (de) | 1997-12-11 | 2005-07-21 | Janssen Pharmaceutica N.V. | Anilide als vitamin-a-säure-mimetika |
JP2002521441A (ja) | 1998-07-28 | 2002-07-16 | スミスクライン・ビーチャム・コーポレイション | Ccr5モジュレーターとしてのプロペンアミド |
JP2002528533A (ja) | 1998-10-29 | 2002-09-03 | ブリストル−マイヤーズ スクイブ カンパニー | 酵素impdhの新規なインヒビター |
-
1999
- 1999-07-27 DE DE19935219A patent/DE19935219A1/de not_active Withdrawn
-
2000
- 2000-07-18 US US09/618,702 patent/US6362210B1/en not_active Expired - Lifetime
- 2000-07-22 SK SK296-2002A patent/SK2962002A3/sk not_active Application Discontinuation
- 2000-07-22 WO PCT/EP2000/007057 patent/WO2001007020A2/de not_active Application Discontinuation
- 2000-07-22 TR TR2002/00226T patent/TR200200226T2/xx unknown
- 2000-07-22 EE EEP200200041A patent/EE200200041A/xx unknown
- 2000-07-22 EP EP00951431A patent/EP1261321A2/de not_active Withdrawn
- 2000-07-22 AU AU64368/00A patent/AU6436800A/en not_active Abandoned
- 2000-07-22 YU YU5502A patent/YU5502A/sh unknown
- 2000-07-22 MX MXPA02000822A patent/MXPA02000822A/es unknown
- 2000-07-22 CA CA002378382A patent/CA2378382C/en not_active Expired - Fee Related
- 2000-07-22 EA EA200200114A patent/EA200200114A1/ru unknown
- 2000-07-22 KR KR1020027001103A patent/KR20020032537A/ko not_active Application Discontinuation
- 2000-07-22 HU HU0204373A patent/HUP0204373A3/hu unknown
- 2000-07-22 CN CN00812829A patent/CN1414849A/zh active Pending
- 2000-07-22 JP JP2001511906A patent/JP5010788B2/ja not_active Expired - Fee Related
- 2000-07-22 BR BR0013184-9A patent/BR0013184A/pt not_active Expired - Fee Related
- 2000-07-22 PL PL36133500A patent/PL361335A1/xx not_active Application Discontinuation
- 2000-07-22 IL IL14770700A patent/IL147707A0/xx unknown
- 2000-07-22 CZ CZ2002313A patent/CZ2002313A3/cs unknown
- 2000-07-25 UY UY26256A patent/UY26256A1/es not_active Application Discontinuation
- 2000-07-26 AR ARP000103858A patent/AR024944A1/es not_active Withdrawn
- 2000-07-27 CO CO00056547A patent/CO5180639A1/es not_active Application Discontinuation
-
2002
- 2002-01-03 US US10/037,555 patent/US6727250B2/en not_active Expired - Lifetime
- 2002-01-23 BG BG106343A patent/BG106343A/xx active Pending
- 2002-01-24 NO NO20020374A patent/NO20020374L/no not_active Application Discontinuation
- 2002-01-25 HR HR20020072A patent/HRP20020072A2/hr not_active Application Discontinuation
- 2002-01-25 ZA ZA200200694A patent/ZA200200694B/en unknown
Also Published As
Publication number | Publication date |
---|---|
CO5180639A1 (es) | 2002-07-30 |
US6727250B2 (en) | 2004-04-27 |
KR20020032537A (ko) | 2002-05-03 |
AR024944A1 (es) | 2002-10-30 |
NO20020374D0 (no) | 2002-01-24 |
PL361335A1 (en) | 2004-10-04 |
EP1261321A2 (de) | 2002-12-04 |
CN1414849A (zh) | 2003-04-30 |
EA200200114A1 (ru) | 2002-12-26 |
CA2378382C (en) | 2008-09-23 |
AU6436800A (en) | 2001-02-13 |
MXPA02000822A (es) | 2002-10-23 |
US6362210B1 (en) | 2002-03-26 |
SK2962002A3 (en) | 2002-06-04 |
JP2003518475A (ja) | 2003-06-10 |
JP5010788B2 (ja) | 2012-08-29 |
US20020099089A1 (en) | 2002-07-25 |
NO20020374L (no) | 2002-01-24 |
CA2378382A1 (en) | 2001-02-01 |
TR200200226T2 (tr) | 2002-09-23 |
CZ2002313A3 (cs) | 2002-06-12 |
YU5502A (sh) | 2005-06-10 |
UY26256A1 (es) | 2001-03-16 |
WO2001007020A3 (de) | 2002-09-19 |
HUP0204373A2 (hu) | 2003-03-28 |
IL147707A0 (en) | 2002-08-14 |
HUP0204373A3 (en) | 2004-12-28 |
BG106343A (en) | 2002-08-30 |
EE200200041A (et) | 2003-04-15 |
WO2001007020A2 (de) | 2001-02-01 |
DE19935219A1 (de) | 2001-02-01 |
ZA200200694B (en) | 2003-09-23 |
BR0013184A (pt) | 2003-07-01 |
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