BE587241A - - Google Patents
Info
- Publication number
- BE587241A BE587241A BE587241DA BE587241A BE 587241 A BE587241 A BE 587241A BE 587241D A BE587241D A BE 587241DA BE 587241 A BE587241 A BE 587241A
- Authority
- BE
- Belgium
- Prior art keywords
- pyrazol
- hydrazine
- hydrazone
- carbon atoms
- ethanol
- Prior art date
Links
- 239000000203 mixture Substances 0.000 claims description 46
- 150000007857 hydrazones Chemical class 0.000 claims description 30
- -1 monophenylamino Chemical group 0.000 claims description 27
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000003937 drug carrier Substances 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- HWAZAXPZGCVLLU-UHFFFAOYSA-N N=1NC=C2C=1C1=CC=CC=C1C2=NN Chemical compound N=1NC=C2C=1C1=CC=CC=C1C2=NN HWAZAXPZGCVLLU-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- NPTFUJRPAPQBTP-UHFFFAOYSA-N 3-propan-2-yl-2H-indeno[1,2-c]pyrazol-4-one Chemical compound C1=CC=C2C(=O)C3=C(C(C)C)NN=C3C2=C1 NPTFUJRPAPQBTP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- KDYKEOKTPKQANU-UHFFFAOYSA-N 3-ethyl-2H-indeno[1,2-c]pyrazol-4-one Chemical compound C1=CC=C2C(=O)C3=C(CC)NN=C3C2=C1 KDYKEOKTPKQANU-UHFFFAOYSA-N 0.000 claims 1
- WMDLBUILMXLFQA-UHFFFAOYSA-N 3-tert-butyl-2H-indeno[1,2-c]pyrazol-4-one Chemical compound C1=CC=C2C(=O)C3=C(C(C)(C)C)NN=C3C2=C1 WMDLBUILMXLFQA-UHFFFAOYSA-N 0.000 claims 1
- KIAHFMUZJNEYTC-UHFFFAOYSA-N C(CC=C)C1=NNC2=C1C(C1=CC=CC=C21)=O Chemical compound C(CC=C)C1=NNC2=C1C(C1=CC=CC=C21)=O KIAHFMUZJNEYTC-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 84
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 78
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 38
- 150000001875 compounds Chemical class 0.000 description 23
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- 238000010992 reflux Methods 0.000 description 20
- 239000007787 solid Substances 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 150000002576 ketones Chemical class 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- 238000009833 condensation Methods 0.000 description 7
- 230000005494 condensation Effects 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- GHFDYLOGYDGRHI-UHFFFAOYSA-N 1H-indeno[1,2-c]pyrazol-4-one Chemical class C12=CC=CC=C2C(=O)C2=C1NN=C2 GHFDYLOGYDGRHI-UHFFFAOYSA-N 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- HAFOQYHPJYVFTI-UHFFFAOYSA-N 3-(4-methoxyphenyl)-1H-indeno[1,2-c]pyrazol-4-one Chemical compound C1=CC(OC)=CC=C1C1=NNC2=C1C(=O)C1=CC=CC=C12 HAFOQYHPJYVFTI-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHKAJLSKXBADFT-UHFFFAOYSA-N 1,3-Indandione Chemical class C1=CC=C2C(=O)CC(=O)C2=C1 UHKAJLSKXBADFT-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 159000000001 potassium salts Chemical class 0.000 description 3
- BZKBCQXYZZXSCO-UHFFFAOYSA-N sodium hydride Chemical compound [H-].[Na+] BZKBCQXYZZXSCO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- OYANRWLUCRFSGL-UHFFFAOYSA-N 3-methyl-2H-indeno[1,2-c]pyrazol-4-one Chemical compound C1=CC=C2C(=O)C3=C(C)NN=C3C2=C1 OYANRWLUCRFSGL-UHFFFAOYSA-N 0.000 description 2
- JJMWVDJMUHFLLC-UHFFFAOYSA-N C(CC)(=O)C1C(C2=CC=C(C=C2C1=O)O)=O Chemical compound C(CC)(=O)C1C(C2=CC=C(C=C2C1=O)O)=O JJMWVDJMUHFLLC-UHFFFAOYSA-N 0.000 description 2
- HTNCDODQEMRLDE-UHFFFAOYSA-N C(CCCCCCC)C1=C2C(=NN1)C1=CC=C(C=C1C2=O)[N+](=O)[O-] Chemical compound C(CCCCCCC)C1=C2C(=NN1)C1=CC=C(C=C1C2=O)[N+](=O)[O-] HTNCDODQEMRLDE-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N Methyl isopropyl ketone Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 230000000994 depressed Effects 0.000 description 2
- 229960001826 dimethylphthalate Drugs 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- XALCHIQGBKVSTD-UHFFFAOYSA-N indeno[1,2-c]pyrazole Chemical class C1=CC=C2C3=NN=CC3=CC2=C1 XALCHIQGBKVSTD-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N methylphenylketone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 230000003285 pharmacodynamic Effects 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N t-BuOH Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- IFZHGQSUNAKKSN-UHFFFAOYSA-N 1,1-diethylhydrazine Chemical compound CCN(N)CC IFZHGQSUNAKKSN-UHFFFAOYSA-N 0.000 description 1
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 1
- TVGMOUGXQYQZOL-UHFFFAOYSA-N 1-(2-ethoxyphenyl)ethanone Chemical compound CCOC1=CC=CC=C1C(C)=O TVGMOUGXQYQZOL-UHFFFAOYSA-N 0.000 description 1
- GPRYKVSEZCQIHD-UHFFFAOYSA-N 1-(4-aminophenyl)ethanone Chemical compound CC(=O)C1=CC=C(N)C=C1 GPRYKVSEZCQIHD-UHFFFAOYSA-N 0.000 description 1
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 1
- YJFNFQHMQJCPRG-UHFFFAOYSA-N 1-(4-ethoxyphenyl)ethanone Chemical compound CCOC1=CC=C(C(C)=O)C=C1 YJFNFQHMQJCPRG-UHFFFAOYSA-N 0.000 description 1
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 1-(4-methylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 1
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-Dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 1
- GWZHPSHQKPBGNN-UHFFFAOYSA-N 2-(2-methylpropanoyl)indene-1,3-dione Chemical compound C1=CC=C2C(=O)C(C(=O)C(C)C)C(=O)C2=C1 GWZHPSHQKPBGNN-UHFFFAOYSA-N 0.000 description 1
- KWVMEUYISWAZHM-UHFFFAOYSA-N 2-(3-methylbut-2-enoyl)indene-1,3-dione Chemical compound C1=CC=C2C(=O)C(C(=O)C=C(C)C)C(=O)C2=C1 KWVMEUYISWAZHM-UHFFFAOYSA-N 0.000 description 1
- MDXWLVDZYYAYPN-UHFFFAOYSA-N 2-(4-chlorobenzoyl)indene-1,3-dione Chemical compound C1=CC(Cl)=CC=C1C(=O)C1C(=O)C2=CC=CC=C2C1=O MDXWLVDZYYAYPN-UHFFFAOYSA-N 0.000 description 1
- NJSFXAKMNPVRCR-UHFFFAOYSA-N 2-(4-methoxybenzoyl)indene-1,3-dione Chemical compound C1=CC(OC)=CC=C1C(=O)C1C(=O)C2=CC=CC=C2C1=O NJSFXAKMNPVRCR-UHFFFAOYSA-N 0.000 description 1
- NQUOLPANTPVAII-UHFFFAOYSA-N 2-acetyl-5-chloroindene-1,3-dione Chemical compound C1=C(Cl)C=C2C(=O)C(C(=O)C)C(=O)C2=C1 NQUOLPANTPVAII-UHFFFAOYSA-N 0.000 description 1
- SGLKFWMIZOJHCL-UHFFFAOYSA-N 2-acetylindene-1,3-dione Chemical compound C1=CC=C2C(=O)C(C(=O)C)C(=O)C2=C1 SGLKFWMIZOJHCL-UHFFFAOYSA-N 0.000 description 1
- UURMMRCWXJLUKF-UHFFFAOYSA-N 2-benzoylindene-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C1C(=O)C1=CC=CC=C1 UURMMRCWXJLUKF-UHFFFAOYSA-N 0.000 description 1
- ACCAZUAGWNCBSI-UHFFFAOYSA-M 2-methoxycarbonyl-5-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1C([O-])=O ACCAZUAGWNCBSI-UHFFFAOYSA-M 0.000 description 1
- CEEJSCAKNYSVHF-UHFFFAOYSA-M 2-methoxycarbonyl-5-nitrobenzoate Chemical compound COC(=O)C1=CC=C([N+]([O-])=O)C=C1C([O-])=O CEEJSCAKNYSVHF-UHFFFAOYSA-M 0.000 description 1
- FNJSWIPFHMKRAT-UHFFFAOYSA-M 2-methoxycarbonylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C([O-])=O FNJSWIPFHMKRAT-UHFFFAOYSA-M 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- KNOZCKSSLOTBPA-UHFFFAOYSA-N 2-propanoylindene-1,3-dione Chemical compound C1=CC=C2C(=O)C(C(=O)CC)C(=O)C2=C1 KNOZCKSSLOTBPA-UHFFFAOYSA-N 0.000 description 1
- OFMZWMXZXVWSPD-UHFFFAOYSA-N 3-benzyl-2H-indeno[1,2-c]pyrazol-4-one Chemical compound C=12C(=O)C3=CC=CC=C3C2=NNC=1CC1=CC=CC=C1 OFMZWMXZXVWSPD-UHFFFAOYSA-N 0.000 description 1
- ZQLIMQLNDJIBLM-UHFFFAOYSA-N 3-cyclohexyl-2H-indeno[1,2-c]pyrazol-4-one Chemical compound C=12C(=O)C3=CC=CC=C3C2=NNC=1C1CCCCC1 ZQLIMQLNDJIBLM-UHFFFAOYSA-N 0.000 description 1
- WBJSAJUPDRXEPQ-UHFFFAOYSA-N 3-phenyl-1H-indeno[1,2-c]pyrazol-4-one Chemical compound C1=2C(=O)C3=CC=CC=C3C=2NN=C1C1=CC=CC=C1 WBJSAJUPDRXEPQ-UHFFFAOYSA-N 0.000 description 1
- WFFZGYRTVIPBFN-UHFFFAOYSA-N 3H-indene-1,2-dione Chemical class C1=CC=C2C(=O)C(=O)CC2=C1 WFFZGYRTVIPBFN-UHFFFAOYSA-N 0.000 description 1
- VVQXVYQQLYWMSW-UHFFFAOYSA-M 6-methoxycarbonyl-2,3-dimethylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(C)=C1C([O-])=O VVQXVYQQLYWMSW-UHFFFAOYSA-M 0.000 description 1
- NTPLXRHDUXRPNE-UHFFFAOYSA-N Acetanisole Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N Acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N Benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N Benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- MATNASBCICRJJO-UHFFFAOYSA-N BrC1=C2C(C=3C(=NNC=3CC(C)C)C2=CC=C1)=O Chemical compound BrC1=C2C(C=3C(=NNC=3CC(C)C)C2=CC=C1)=O MATNASBCICRJJO-UHFFFAOYSA-N 0.000 description 1
- MYECHICWLINXOP-UHFFFAOYSA-N BrC=1C=C2C(C(C(C2=CC1)=O)C(CC(C)C)=O)=O Chemical compound BrC=1C=C2C(C(C(C2=CC1)=O)C(CC(C)C)=O)=O MYECHICWLINXOP-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N Bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- UWVOXYSRKABDCT-UHFFFAOYSA-N C(C(C)C)(=O)C1C(C2=CC=C(C=C2C1=O)I)=O Chemical compound C(C(C)C)(=O)C1C(C2=CC=C(C=C2C1=O)I)=O UWVOXYSRKABDCT-UHFFFAOYSA-N 0.000 description 1
- WCQQPBLNCALJFM-UHFFFAOYSA-M C(C)(=O)OC=1C=C(C(C(=O)OC)=CC=1OC)C(=O)[O-] Chemical compound C(C)(=O)OC=1C=C(C(C(=O)OC)=CC=1OC)C(=O)[O-] WCQQPBLNCALJFM-UHFFFAOYSA-M 0.000 description 1
- OBRZUXPTOFPOGT-UHFFFAOYSA-N C(C)(C)C1=C2C(=NN1)C1=C(C(=C(C(=C1C2=O)Cl)Cl)Cl)Cl Chemical compound C(C)(C)C1=C2C(=NN1)C1=C(C(=C(C(=C1C2=O)Cl)Cl)Cl)Cl OBRZUXPTOFPOGT-UHFFFAOYSA-N 0.000 description 1
- ILULMWCXFYRBQP-UHFFFAOYSA-N C(C)(C)C1=C2C(=NN1)C1=CC=C(C=C1C2=NN)I Chemical compound C(C)(C)C1=C2C(=NN1)C1=CC=C(C=C1C2=NN)I ILULMWCXFYRBQP-UHFFFAOYSA-N 0.000 description 1
- NEPBKNALNOPHLA-UHFFFAOYSA-M C(C)OC1=C(C(C(=O)OCC)=C(C=C1OC)[N+](=O)[O-])C(=O)[O-] Chemical compound C(C)OC1=C(C(C(=O)OCC)=C(C=C1OC)[N+](=O)[O-])C(=O)[O-] NEPBKNALNOPHLA-UHFFFAOYSA-M 0.000 description 1
- NMRLNAXSLRNCCX-UHFFFAOYSA-N C(CCCCCCC)C1=C2C(=NN1)C1=CC=C(C=C1C2=O)N Chemical compound C(CCCCCCC)C1=C2C(=NN1)C1=CC=C(C=C1C2=O)N NMRLNAXSLRNCCX-UHFFFAOYSA-N 0.000 description 1
- QVOUMFBACNTNOU-UHFFFAOYSA-N C(CCCCCCCC)(=O)C1C(C2=CC=C(C=C2C1=O)[N+](=O)[O-])=O Chemical compound C(CCCCCCCC)(=O)C1C(C2=CC=C(C=C2C1=O)[N+](=O)[O-])=O QVOUMFBACNTNOU-UHFFFAOYSA-N 0.000 description 1
- CLXCICZGHHKYPY-UHFFFAOYSA-N CC(=CC1=C2C(=NN1)C1=CC=CC=C1C2=O)C Chemical compound CC(=CC1=C2C(=NN1)C1=CC=CC=C1C2=O)C CLXCICZGHHKYPY-UHFFFAOYSA-N 0.000 description 1
- FVXGMEHRYVJKAK-UHFFFAOYSA-N CC1=C2C(C(C(C2=CC=C1C)=O)C(C(C)C)=O)=O Chemical compound CC1=C2C(C(C(C2=CC=C1C)=O)C(C(C)C)=O)=O FVXGMEHRYVJKAK-UHFFFAOYSA-N 0.000 description 1
- MKWUFRXSOJZSHG-UHFFFAOYSA-N CC1=CC=C(C(=O)C2C(C3=CC=C(C=C3C2=O)C)=O)C=C1 Chemical compound CC1=CC=C(C(=O)C2C(C3=CC=C(C=C3C2=O)C)=O)C=C1 MKWUFRXSOJZSHG-UHFFFAOYSA-N 0.000 description 1
- QXCLDJTWECJKMX-UHFFFAOYSA-N CC1=CC=C(C=C1)C1=C2C(=NN1)C1=CC=C(C=C1C2=NN)C Chemical compound CC1=CC=C(C=C1)C1=C2C(=NN1)C1=CC=C(C=C1C2=NN)C QXCLDJTWECJKMX-UHFFFAOYSA-N 0.000 description 1
- WFCHAIMQUUYYMT-UHFFFAOYSA-M COC1=C(C(C(=O)OCC)=C(C=C1)OC)C(=O)[O-] Chemical compound COC1=C(C(C(=O)OCC)=C(C=C1)OC)C(=O)[O-] WFCHAIMQUUYYMT-UHFFFAOYSA-M 0.000 description 1
- NLYQJSJOUXAQLZ-UHFFFAOYSA-N COC1=C2C(C(C(C2=C(C=C1)OC)=O)C(C1=CC=C(C=C1)OCC)=O)=O Chemical compound COC1=C2C(C(C(C2=C(C=C1)OC)=O)C(C1=CC=C(C=C1)OCC)=O)=O NLYQJSJOUXAQLZ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 210000003169 Central Nervous System Anatomy 0.000 description 1
- PEKBJZMUMAPZQS-UHFFFAOYSA-N ClC=1C=C2C(C=3C(=NNC=3C)C2=CC=1)=O Chemical compound ClC=1C=C2C(C=3C(=NNC=3C)C2=CC=1)=O PEKBJZMUMAPZQS-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FBPFZTCFMRRESA-KAZBKCHUSA-N D-Mannitol Natural products OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KAZBKCHUSA-N 0.000 description 1
- GUBGYTABKSRVRQ-UUNJERMWSA-N Lactose Natural products O([C@@H]1[C@H](O)[C@H](O)[C@H](O)O[C@@H]1CO)[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1 GUBGYTABKSRVRQ-UUNJERMWSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- ZWLFHBDHXZMFAH-UHFFFAOYSA-N NC1=CC=C(C(=O)C2C(C3=CC=CC=C3C2=O)=O)C=C1 Chemical compound NC1=CC=C(C(=O)C2C(C3=CC=CC=C3C2=O)=O)C=C1 ZWLFHBDHXZMFAH-UHFFFAOYSA-N 0.000 description 1
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- HKOOXMFOFWEVGF-UHFFFAOYSA-N Phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
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- 229920002472 Starch Polymers 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
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- 238000007792 addition Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
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- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
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- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical compound CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- MJKJAEIWPTVMSW-UHFFFAOYSA-N dimethyl 4-acetyloxybenzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC=C(OC(C)=O)C=C1C(=O)OC MJKJAEIWPTVMSW-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- HQWKKEIVHQXCPI-UHFFFAOYSA-L disodium;phthalate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C([O-])=O HQWKKEIVHQXCPI-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- CHDFNIZLAAFFPX-UHFFFAOYSA-N ethoxyethane;oxolane Chemical compound CCOCC.C1CCOC1 CHDFNIZLAAFFPX-UHFFFAOYSA-N 0.000 description 1
- FFLYUXVZEPLMCL-UHFFFAOYSA-N ethylchloranuidyl formate Chemical compound CC[Cl-]OC=O FFLYUXVZEPLMCL-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- KLGZELKXQMTEMM-UHFFFAOYSA-N hydride Chemical compound [H-] KLGZELKXQMTEMM-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Chemical group 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
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- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- UAVOCTDYPKOULU-UHFFFAOYSA-N methylchloranuidyl formate Chemical compound C[Cl-]OC=O UAVOCTDYPKOULU-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- 230000003000 nontoxic Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- OCFVSFVLVRNXFJ-UHFFFAOYSA-N potassium hydride Inorganic materials [H-].[K+] OCFVSFVLVRNXFJ-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
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- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003385 sodium Chemical group 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-M stearate Chemical compound CCCCCCCCCCCCCCCCCC([O-])=O QIQXTHQIDYTFRH-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000002936 tranquilizing Effects 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE587241A true BE587241A (es) |
Family
ID=191669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE587241D BE587241A (es) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE587241A (es) |
-
0
- BE BE587241D patent/BE587241A/fr unknown
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