HRP20041073A2 - Indole derivatives, method for preparing same and pharmaceutical compositions containing same - Google Patents
Indole derivatives, method for preparing same and pharmaceutical compositions containing sameInfo
- Publication number
- HRP20041073A2 HRP20041073A2 HRP20041073A HRP20041073A2 HR P20041073 A2 HRP20041073 A2 HR P20041073A2 HR P20041073 A HRP20041073 A HR P20041073A HR P20041073 A2 HRP20041073 A2 HR P20041073A2
- Authority
- HR
- Croatia
- Prior art keywords
- group
- formula
- compound
- alkyl
- alkyl group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 55
- 150000002475 indoles Chemical class 0.000 title abstract description 7
- 229940054051 antipsychotic indole derivative Drugs 0.000 title abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 238000002360 preparation method Methods 0.000 claims abstract description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 37
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 239000012453 solvate Substances 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 101100533888 Hypocrea jecorina (strain QM6a) sor4 gene Proteins 0.000 claims abstract description 7
- 101100533877 Hypocrea jecorina (strain QM6a) sor8 gene Proteins 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 99
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 31
- 125000005843 halogen group Chemical group 0.000 claims description 27
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- -1 nitro, hydroxy Chemical group 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 10
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 10
- 239000013543 active substance Substances 0.000 claims description 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 102000009135 CB2 Cannabinoid Receptor Human genes 0.000 claims description 7
- 108010073376 CB2 Cannabinoid Receptor Proteins 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000002393 azetidinyl group Chemical group 0.000 claims description 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 208000023275 Autoimmune disease Diseases 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 2
- 208000008589 Obesity Diseases 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 150000002443 hydroxylamines Chemical class 0.000 claims description 2
- 208000015181 infectious disease Diseases 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 235000020824 obesity Nutrition 0.000 claims description 2
- 230000007170 pathology Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 230000001629 suppression Effects 0.000 claims 2
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 230000007815 allergy Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 125000002947 alkylene group Chemical group 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 35
- 239000000203 mixture Substances 0.000 description 32
- 239000000243 solution Substances 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 238000005481 NMR spectroscopy Methods 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000012299 nitrogen atmosphere Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 102000018208 Cannabinoid Receptor Human genes 0.000 description 11
- 108050007331 Cannabinoid receptor Proteins 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- XGLVDUUYFKXKPL-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n,n-bis[2-(2-methoxyethoxy)ethyl]ethanamine Chemical compound COCCOCCN(CCOCCOC)CCOCCOC XGLVDUUYFKXKPL-UHFFFAOYSA-N 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 229930003827 cannabinoid Natural products 0.000 description 5
- 239000003557 cannabinoid Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000002152 alkylating effect Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229940065144 cannabinoids Drugs 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 208000002551 irritable bowel syndrome Diseases 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 3
- 208000002193 Pain Diseases 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 210000002540 macrophage Anatomy 0.000 description 3
- UZNGRHDUJIVHQT-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].C[C-]=C UZNGRHDUJIVHQT-UHFFFAOYSA-M 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- RIKGRFSGIOOYEK-UHFFFAOYSA-N 2-fluoro-3-(trifluoromethyl)benzoyl chloride Chemical compound FC1=C(C(Cl)=O)C=CC=C1C(F)(F)F RIKGRFSGIOOYEK-UHFFFAOYSA-N 0.000 description 2
- PGKVRCDOBBACEN-UHFFFAOYSA-N 6,7-dichloro-2-methyl-1h-indole Chemical compound C1=C(Cl)C(Cl)=C2NC(C)=CC2=C1 PGKVRCDOBBACEN-UHFFFAOYSA-N 0.000 description 2
- YFEGQGALXHJBIQ-UHFFFAOYSA-N 7-bromo-2-methyl-1h-indole Chemical compound C1=CC(Br)=C2NC(C)=CC2=C1 YFEGQGALXHJBIQ-UHFFFAOYSA-N 0.000 description 2
- YIJQQOHTYWFLQH-UHFFFAOYSA-N 7-chloro-2-methyl-1h-indole Chemical compound C1=CC(Cl)=C2NC(C)=CC2=C1 YIJQQOHTYWFLQH-UHFFFAOYSA-N 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- 102000009132 CB1 Cannabinoid Receptor Human genes 0.000 description 2
- 108010073366 CB1 Cannabinoid Receptor Proteins 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000008050 dialkyl sulfates Chemical class 0.000 description 2
- 150000002366 halogen compounds Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 210000004698 lymphocyte Anatomy 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- POSMIGJZZDTBHR-UHFFFAOYSA-N n-[3-[6,7-dichloro-3-[2-fluoro-3-(trifluoromethyl)benzoyl]-2-methylindol-1-yl]propyl]methanesulfonamide Chemical compound C12=CC=C(Cl)C(Cl)=C2N(CCCNS(C)(=O)=O)C(C)=C1C(=O)C1=CC=CC(C(F)(F)F)=C1F POSMIGJZZDTBHR-UHFFFAOYSA-N 0.000 description 2
- XUXSBTKOIPCCIC-UHFFFAOYSA-N n-[3-[7-chloro-3-[2-fluoro-3-(trifluoromethyl)phenyl]-2-methylindol-1-yl]propyl]methanesulfonamide Chemical compound C12=CC=CC(Cl)=C2N(CCCNS(C)(=O)=O)C(C)=C1C1=CC=CC(C(F)(F)F)=C1F XUXSBTKOIPCCIC-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000036407 pain Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 210000002345 respiratory system Anatomy 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 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 2
- GNLJBJNONOOOQC-UHFFFAOYSA-N $l^{3}-carbane;magnesium Chemical class [Mg]C GNLJBJNONOOOQC-UHFFFAOYSA-N 0.000 description 1
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
- JCKFKSYROBMKEM-UHFFFAOYSA-N (7-bromo-2-methyl-1h-indol-3-yl)-(2,3-dichlorophenyl)methanone Chemical compound CC=1NC2=C(Br)C=CC=C2C=1C(=O)C1=CC=CC(Cl)=C1Cl JCKFKSYROBMKEM-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- CMVQZRLQEOAYSW-UHFFFAOYSA-N 1,2-dichloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1Cl CMVQZRLQEOAYSW-UHFFFAOYSA-N 0.000 description 1
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 1
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YBONBWJSFMTXLE-UHFFFAOYSA-N 2,3-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(Cl)=C1Cl YBONBWJSFMTXLE-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- BXGYBSJAZFGIPX-UHFFFAOYSA-N 2-pyridin-2-ylethanol Chemical compound OCCC1=CC=CC=N1 BXGYBSJAZFGIPX-UHFFFAOYSA-N 0.000 description 1
- LJQNMDZRCXJETK-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine;hydron;chloride Chemical compound Cl.CN(C)CCCCl LJQNMDZRCXJETK-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- QCRHRKLUDQTLBU-UHFFFAOYSA-N 6,7-dichloro-1-(3-chloropropyl)-2-methylindole Chemical compound C1=C(Cl)C(Cl)=C2N(CCCCl)C(C)=CC2=C1 QCRHRKLUDQTLBU-UHFFFAOYSA-N 0.000 description 1
- LKBNHTNNSBUPGC-UHFFFAOYSA-N 6,7-dichloro-1-(3-iodopropyl)-2-methylindole Chemical compound C1=C(Cl)C(Cl)=C2N(CCCI)C(C)=CC2=C1 LKBNHTNNSBUPGC-UHFFFAOYSA-N 0.000 description 1
- MVMRVNLBCYLBDG-UHFFFAOYSA-N 7-chloro-1-(1-chloropropyl)-2-methylindole Chemical compound C1=CC(Cl)=C2N(C(Cl)CC)C(C)=CC2=C1 MVMRVNLBCYLBDG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 208000000044 Amnesia Diseases 0.000 description 1
- 229920000856 Amylose Polymers 0.000 description 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 206010003267 Arthritis reactive Diseases 0.000 description 1
- 206010003571 Astrocytoma Diseases 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Psychiatry (AREA)
- Ophthalmology & Optometry (AREA)
- Dermatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Virology (AREA)
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- Oncology (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Psychology (AREA)
- Obesity (AREA)
- Otolaryngology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0206133A FR2839718B1 (fr) | 2002-05-17 | 2002-05-17 | Derives d'indole, leur procede de preparation et les compositions pharmaceutiques en contenant |
| PCT/FR2003/001470 WO2003097597A2 (fr) | 2002-05-17 | 2003-05-15 | Derives d'indole et leur utilisation en tant que ligands des recepteurs cb2 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20041073A2 true HRP20041073A2 (en) | 2004-12-31 |
Family
ID=29286599
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20041073 HRP20041073A2 (en) | 2002-05-17 | 2004-11-16 | Indole derivatives, method for preparing same and pharmaceutical compositions containing same |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US7138424B2 (de) |
| EP (1) | EP1507758B1 (de) |
| JP (1) | JP2005530797A (de) |
| KR (1) | KR20040106560A (de) |
| CN (1) | CN1668588A (de) |
| AT (1) | ATE308518T1 (de) |
| AU (1) | AU2003258762A1 (de) |
| BR (1) | BR0311185A (de) |
| CA (1) | CA2482756A1 (de) |
| DE (1) | DE60302156T2 (de) |
| EA (1) | EA200401315A1 (de) |
| FR (1) | FR2839718B1 (de) |
| HR (1) | HRP20041073A2 (de) |
| IL (1) | IL164941A0 (de) |
| IS (1) | IS7513A (de) |
| MA (1) | MA27203A1 (de) |
| MX (1) | MXPA04011387A (de) |
| NO (1) | NO20044970L (de) |
| PL (1) | PL374111A1 (de) |
| WO (1) | WO2003097597A2 (de) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7067539B2 (en) * | 2001-02-08 | 2006-06-27 | Schering Corporation | Cannabinoid receptor ligands |
| UY27939A1 (es) | 2002-08-21 | 2004-03-31 | Glaxo Group Ltd | Compuestos |
| TW200505902A (en) * | 2003-03-20 | 2005-02-16 | Schering Corp | Cannabinoid receptor ligands |
| GB0402355D0 (en) * | 2004-02-03 | 2004-03-10 | Glaxo Group Ltd | Novel compounds |
| TW200533657A (en) * | 2004-02-17 | 2005-10-16 | Esteve Labor Dr | Substituted pyrazoline compounds, their preparation and use as medicaments |
| US20090042820A1 (en) * | 2004-11-22 | 2009-02-12 | Threshold Pharmaceuticals, Inc. | Tubulin Binding Anti Cancer Agents And Prodrugs Thereof |
| EP1743892A1 (de) | 2005-07-15 | 2007-01-17 | Laboratorios del Dr. Esteve S.A. | Substituierte Pyrazolin Verbindungen, deren Herstellung und Verwendung als Medikament |
| FR2893615B1 (fr) * | 2005-11-18 | 2008-03-07 | Sanofi Aventis Sa | Derives de 3-acylindole, leur preparation et leur application en therapeutique |
| GB0702862D0 (en) * | 2007-02-14 | 2007-03-28 | Univ Aberdeen | Therapeutic compounds |
| JP5272008B2 (ja) * | 2007-08-29 | 2013-08-28 | メルク・シャープ・アンド・ドーム・コーポレーション | 置換インドール誘導体およびその使用の方法 |
| FR2933697B1 (fr) | 2008-07-11 | 2010-08-13 | Sanofi Aventis | Derives de 1-benzyl-cinnolin-4-(1h)-one substitues, leur preparation et leur application en therapeutique |
| FR2950055A1 (fr) | 2009-09-17 | 2011-03-18 | Sanofi Aventis | Derives de 3-amino-cinnolin-4(1h)-one substitues, leur preparation et leur application en therapeutique |
| FR2983859B1 (fr) | 2011-12-12 | 2014-01-17 | Sanofi Sa | Derives de 1,3,5-triazine-2-amine, leur preparation et leur application en diagnostique et en therapeutique |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2735774B1 (fr) | 1995-06-21 | 1997-09-12 | Sanofi Sa | Utilisation de composes agonistes du recepteur cb2 humain pour la preparation de medicaments immunomodulateurs, nouveaux composes agonistes du recepteur cb2 et les compositions pharmaceutiques les contenant |
| WO2001028557A1 (en) * | 1999-10-18 | 2001-04-26 | University Of Connecticut | Cannabimimetic indole derivatives |
-
2002
- 2002-05-17 FR FR0206133A patent/FR2839718B1/fr not_active Expired - Fee Related
-
2003
- 2003-05-15 CA CA002482756A patent/CA2482756A1/fr not_active Abandoned
- 2003-05-15 DE DE60302156T patent/DE60302156T2/de not_active Expired - Lifetime
- 2003-05-15 WO PCT/FR2003/001470 patent/WO2003097597A2/fr active IP Right Grant
- 2003-05-15 AT AT03752808T patent/ATE308518T1/de not_active IP Right Cessation
- 2003-05-15 MX MXPA04011387A patent/MXPA04011387A/es not_active Application Discontinuation
- 2003-05-15 KR KR10-2004-7018491A patent/KR20040106560A/ko not_active Application Discontinuation
- 2003-05-15 EP EP03752808A patent/EP1507758B1/de not_active Expired - Lifetime
- 2003-05-15 AU AU2003258762A patent/AU2003258762A1/en not_active Abandoned
- 2003-05-15 EA EA200401315A patent/EA200401315A1/ru unknown
- 2003-05-15 US US10/514,309 patent/US7138424B2/en not_active Expired - Fee Related
- 2003-05-15 BR BR0311185-7A patent/BR0311185A/pt not_active Application Discontinuation
- 2003-05-15 JP JP2004505330A patent/JP2005530797A/ja not_active Withdrawn
- 2003-05-15 PL PL03374111A patent/PL374111A1/xx not_active Application Discontinuation
- 2003-05-15 CN CNA038164086A patent/CN1668588A/zh active Pending
-
2004
- 2004-10-20 IS IS7513A patent/IS7513A/is unknown
- 2004-10-31 IL IL16494104A patent/IL164941A0/xx unknown
- 2004-11-09 MA MA27941A patent/MA27203A1/fr unknown
- 2004-11-15 NO NO20044970A patent/NO20044970L/no not_active Application Discontinuation
- 2004-11-16 HR HRP20041073 patent/HRP20041073A2/hr not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1507758B1 (de) | 2005-11-02 |
| MA27203A1 (fr) | 2005-01-03 |
| IL164941A0 (en) | 2005-12-18 |
| IS7513A (is) | 2004-10-20 |
| NO20044970L (no) | 2005-02-17 |
| CA2482756A1 (fr) | 2003-11-27 |
| KR20040106560A (ko) | 2004-12-17 |
| CN1668588A (zh) | 2005-09-14 |
| EP1507758A2 (de) | 2005-02-23 |
| EA200401315A1 (ru) | 2005-04-28 |
| MXPA04011387A (es) | 2005-02-14 |
| WO2003097597A3 (fr) | 2004-04-01 |
| BR0311185A (pt) | 2005-02-22 |
| US7138424B2 (en) | 2006-11-21 |
| FR2839718B1 (fr) | 2004-06-25 |
| WO2003097597A2 (fr) | 2003-11-27 |
| DE60302156D1 (de) | 2005-12-08 |
| PL374111A1 (en) | 2005-10-03 |
| AU2003258762A1 (en) | 2003-12-02 |
| US20060089345A1 (en) | 2006-04-27 |
| ATE308518T1 (de) | 2005-11-15 |
| FR2839718A1 (fr) | 2003-11-21 |
| JP2005530797A (ja) | 2005-10-13 |
| DE60302156T2 (de) | 2006-07-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1OB | Publication of a patent application | ||
| ARAI | Request for the grant of a patent on the basis of the submitted results of a substantive examination of a patent application | ||
| OBST | Application withdrawn |