JPH10237071A - 新規２−アミノインダン化合物、その製造法、及びそれらを含有する医薬組成物 - Google Patents
新規２−アミノインダン化合物、その製造法、及びそれらを含有する医薬組成物Info
- Publication number
- JPH10237071A JPH10237071A JP10042716A JP4271698A JPH10237071A JP H10237071 A JPH10237071 A JP H10237071A JP 10042716 A JP10042716 A JP 10042716A JP 4271698 A JP4271698 A JP 4271698A JP H10237071 A JPH10237071 A JP H10237071A
- Authority
- JP
- Japan
- Prior art keywords
- piperidine
- amino
- dihydro
- compound
- benzodioxin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 2-aminoindane compound Chemical class 0.000 title claims description 34
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 80
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 17
- 239000002253 acid Substances 0.000 claims abstract description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
- 208000035475 disorder Diseases 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 230000003287 optical effect Effects 0.000 claims abstract description 6
- KQNGVKMDIANDHU-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-n-(2,3-dihydro-1h-inden-2-yl)piperidin-4-amine Chemical compound O1CCOC2=C1C=CC=C2N(CC1)CCC1NC1CC2=CC=CC=C2C1 KQNGVKMDIANDHU-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 208000020016 psychiatric disease Diseases 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 64
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 20
- 239000000460 chlorine Substances 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 6
- 239000012279 sodium borohydride Substances 0.000 claims description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 230000000862 serotonergic effect Effects 0.000 claims description 5
- 239000012321 sodium triacetoxyborohydride Substances 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 230000036506 anxiety Effects 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- UNUJRVRWPYDMAF-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-n-(5-fluoro-2,3-dihydro-1h-inden-2-yl)piperidin-4-amine Chemical compound O1CCOC2=C1C=CC=C2N(CC1)CCC1NC1CC2=CC=C(F)C=C2C1 UNUJRVRWPYDMAF-UHFFFAOYSA-N 0.000 claims description 3
- MXNPZIASPIXENL-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-n-(6,7-dihydro-5h-cyclopenta[f][1,3]benzodioxol-6-yl)piperidin-4-amine Chemical compound O1CCOC2=C1C=CC=C2N(CC1)CCC1NC1CC(C=C2OCOC2=C2)=C2C1 MXNPZIASPIXENL-UHFFFAOYSA-N 0.000 claims description 3
- LZLFUVVRGYHCMN-UHFFFAOYSA-N 1-(3,4-dihydro-2h-chromen-8-yl)-n-(2,3-dihydro-1h-inden-2-yl)piperidin-4-amine Chemical compound C1CCOC2=C1C=CC=C2N(CC1)CCC1NC1CC2=CC=CC=C2C1 LZLFUVVRGYHCMN-UHFFFAOYSA-N 0.000 claims description 3
- FKSPATRLBQPGIQ-UHFFFAOYSA-N 2-[[1-(2,3-dihydro-1,4-benzodioxin-5-yl)piperidin-4-yl]amino]-2,3-dihydro-1h-inden-5-ol Chemical compound O1CCOC2=C1C=CC=C2N(CC1)CCC1NC1CC2=CC=C(O)C=C2C1 FKSPATRLBQPGIQ-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000006268 reductive amination reaction Methods 0.000 claims description 3
- IIMOAOXQJWKTRB-UHFFFAOYSA-N 1-(1-benzofuran-7-yl)-n-(5-fluoro-2,3-dihydro-1h-inden-2-yl)piperidin-4-amine Chemical compound C1C2=CC(F)=CC=C2CC1NC(CC1)CCN1C1=CC=CC2=C1OC=C2 IIMOAOXQJWKTRB-UHFFFAOYSA-N 0.000 claims description 2
- IKZLCMYKNSOJJR-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-n-(2,3-dihydro-1h-inden-2-yl)-4-methylpiperidin-4-amine Chemical compound C1C2=CC=CC=C2CC1NC1(C)CCN(C=2C=3OCCOC=3C=CC=2)CC1 IKZLCMYKNSOJJR-UHFFFAOYSA-N 0.000 claims description 2
- GCSHIBJXHHIABB-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-n-(2,3-dihydro-1h-inden-2-yl)-n-methylpiperidin-4-amine Chemical compound O1CCOC2=C1C=CC=C2N(CC1)CCC1N(C)C1CC2=CC=CC=C2C1 GCSHIBJXHHIABB-UHFFFAOYSA-N 0.000 claims description 2
- YMOIEAFLSQBGLL-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-n-(2,3-dihydro-1h-inden-2-yl)pyrrolidin-3-amine Chemical compound O1CCOC2=C1C=CC=C2N1CCC(NC2CC3=CC=CC=C3C2)C1 YMOIEAFLSQBGLL-UHFFFAOYSA-N 0.000 claims description 2
- PEEYUYFAZNTREO-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-n-(4,7-dimethoxy-2,3-dihydro-1h-inden-2-yl)piperidin-4-amine Chemical compound O1CCOC2=C1C=CC=C2N(CC1)CCC1NC1CC(C(OC)=CC=C2OC)=C2C1 PEEYUYFAZNTREO-UHFFFAOYSA-N 0.000 claims description 2
- ZHDLIVXDDCZBDR-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-n-(5,6-dimethoxy-2,3-dihydro-1h-inden-2-yl)piperidin-4-amine Chemical compound O1CCOC2=C1C=CC=C2N(CC1)CCC1NC1CC(C=C(C(=C2)OC)OC)=C2C1 ZHDLIVXDDCZBDR-UHFFFAOYSA-N 0.000 claims description 2
- RIFGFCMZLBEHKB-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-n-(5,6-dimethyl-2,3-dihydro-1h-inden-2-yl)piperidin-4-amine Chemical compound O1CCOC2=C1C=CC=C2N(CC1)CCC1NC1CC(C=C(C(=C2)C)C)=C2C1 RIFGFCMZLBEHKB-UHFFFAOYSA-N 0.000 claims description 2
- CAHPKHAYVYBJAS-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-n-(5-methoxy-2,3-dihydro-1h-inden-2-yl)piperidin-4-amine Chemical compound O1CCOC2=C1C=CC=C2N(CC1)CCC1NC1CC2=CC=C(OC)C=C2C1 CAHPKHAYVYBJAS-UHFFFAOYSA-N 0.000 claims description 2
- BUVGYTAHPWYIHL-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-n-(5-methyl-2,3-dihydro-1h-inden-2-yl)piperidin-4-amine Chemical compound O1CCOC2=C1C=CC=C2N(CC1)CCC1NC1CC2=CC=C(C)C=C2C1 BUVGYTAHPWYIHL-UHFFFAOYSA-N 0.000 claims description 2
- IMVGGCKYFHDIGP-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-n-(5-nitro-2,3-dihydro-1h-inden-2-yl)piperidin-4-amine Chemical compound O1CCOC2=C1C=CC=C2N(CC1)CCC1NC1CC2=CC=C([N+](=O)[O-])C=C2C1 IMVGGCKYFHDIGP-UHFFFAOYSA-N 0.000 claims description 2
- HPEIHRXXYHODTL-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-n-[5-(trifluoromethyl)-2,3-dihydro-1h-inden-2-yl]piperidin-4-amine Chemical compound O1CCOC2=C1C=CC=C2N(CC1)CCC1NC1CC2=CC=C(C(F)(F)F)C=C2C1 HPEIHRXXYHODTL-UHFFFAOYSA-N 0.000 claims description 2
- DIFUSAAJEXBWDZ-UHFFFAOYSA-N 1-(2,3-dihydro-1-benzofuran-7-yl)-n-(5-fluoro-2,3-dihydro-1h-inden-2-yl)piperidin-4-amine Chemical compound C1C2=CC(F)=CC=C2CC1NC(CC1)CCN1C1=CC=CC2=C1OCC2 DIFUSAAJEXBWDZ-UHFFFAOYSA-N 0.000 claims description 2
- RJDOVNUUXOKEOU-UHFFFAOYSA-N 1-(3,4-dihydro-2h-chromen-8-yl)-n-(5-fluoro-2,3-dihydro-1h-inden-2-yl)piperidin-4-amine Chemical compound C1CCOC2=C1C=CC=C2N(CC1)CCC1NC1CC2=CC=C(F)C=C2C1 RJDOVNUUXOKEOU-UHFFFAOYSA-N 0.000 claims description 2
- GYRHSRZYIFQPEU-UHFFFAOYSA-N 1-(3,4-dihydro-2h-chromen-8-yl)-n-(5-methoxy-2,3-dihydro-1h-inden-2-yl)piperidin-4-amine Chemical compound C1CCOC2=C1C=CC=C2N(CC1)CCC1NC1CC2=CC=C(OC)C=C2C1 GYRHSRZYIFQPEU-UHFFFAOYSA-N 0.000 claims description 2
- RCBHFTIWVWXGBL-UHFFFAOYSA-N 1-(3,4-dihydro-2h-chromen-8-yl)-n-(6,7-dihydro-5h-cyclopenta[f][1,3]benzodioxol-6-yl)piperidin-4-amine Chemical compound C1CCOC2=C1C=CC=C2N(CC1)CCC1NC1CC(C=C2OCOC2=C2)=C2C1 RCBHFTIWVWXGBL-UHFFFAOYSA-N 0.000 claims description 2
- VPVYSMHKTMCEEJ-UHFFFAOYSA-N 1-(3,4-dihydro-2h-chromen-8-yl)-n-[5-(1,2,4-triazol-4-yl)-2,3-dihydro-1h-inden-2-yl]piperidin-4-amine Chemical compound C=1C=C2CC(NC3CCN(CC3)C=3C=4OCCCC=4C=CC=3)CC2=CC=1N1C=NN=C1 VPVYSMHKTMCEEJ-UHFFFAOYSA-N 0.000 claims description 2
- JNWIJVIWQUVKQS-UHFFFAOYSA-N 2-[[1-(3,4-dihydro-2h-chromen-8-yl)piperidin-4-yl]amino]-2,3-dihydro-1h-inden-5-ol Chemical compound C1CCOC2=C1C=CC=C2N(CC1)CCC1NC1CC2=CC=C(O)C=C2C1 JNWIJVIWQUVKQS-UHFFFAOYSA-N 0.000 claims description 2
- OGFMFRWOQWESLG-UHFFFAOYSA-N 8-[4-(6,7-dihydro-5h-cyclopenta[f][1,3]benzodioxol-6-ylamino)piperidin-1-yl]-3,4-dihydro-2h-chromen-4-ol Chemical compound C1C2=CC=3OCOC=3C=C2CC1NC(CC1)CCN1C1=CC=CC2=C1OCCC2O OGFMFRWOQWESLG-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 208000008589 Obesity Diseases 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 230000005540 biological transmission Effects 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 230000004064 dysfunction Effects 0.000 claims description 2
- 229910052740 iodine Chemical group 0.000 claims description 2
- 239000011630 iodine Chemical group 0.000 claims description 2
- KGSJYPZELGLEKH-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-1-(3,4-dihydro-2h-thiochromen-8-yl)piperidin-4-amine Chemical compound C1CCSC2=C1C=CC=C2N(CC1)CCC1NC1CC2=CC=CC=C2C1 KGSJYPZELGLEKH-UHFFFAOYSA-N 0.000 claims description 2
- MJVBMEVMDBMTPD-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-1-(6-fluoro-3,4-dihydro-2h-chromen-8-yl)piperidin-4-amine Chemical compound C1C2=CC=CC=C2CC1NC(CC1)CCN1C1=CC(F)=CC2=C1OCCC2 MJVBMEVMDBMTPD-UHFFFAOYSA-N 0.000 claims description 2
- FCQFWLMWZZXDGR-UHFFFAOYSA-N n-(5-chloro-2,3-dihydro-1h-inden-2-yl)-1-(2,3-dihydro-1,4-benzodioxin-5-yl)piperidin-4-amine Chemical compound O1CCOC2=C1C=CC=C2N(CC1)CCC1NC1CC2=CC=C(Cl)C=C2C1 FCQFWLMWZZXDGR-UHFFFAOYSA-N 0.000 claims description 2
- BIPGUBIGRBEVBR-UHFFFAOYSA-N n-[1-(3,4-dihydro-2h-chromen-8-yl)piperidin-4-yl]-3h-cyclopenta[f][2,1,3]benzoxadiazol-6-amine Chemical compound C=1C2=NONC2=CC2=CC(NC3CCN(CC3)C3=CC=CC4=C3OCCC4)=CC2=1 BIPGUBIGRBEVBR-UHFFFAOYSA-N 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
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims 1
- 125000004130 indan-2-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])(*)C2([H])[H] 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 abstract description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 abstract 1
- 230000002295 serotoninergic effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 135
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
- 238000002360 preparation method Methods 0.000 description 46
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 102000005962 receptors Human genes 0.000 description 18
- 108020003175 receptors Proteins 0.000 description 18
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 18
- 238000010992 reflux Methods 0.000 description 17
- 239000000377 silicon dioxide Substances 0.000 description 16
- 239000003480 eluent Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 10
- 238000001035 drying Methods 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000000155 melt Substances 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 229940076279 serotonin Drugs 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 230000027455 binding Effects 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- BFKBHPVGDFWCCR-UHFFFAOYSA-N 5,7-dihydrocyclopenta[f][1,3]benzodioxol-6-one Chemical compound C1=C2CC(=O)CC2=CC2=C1OCO2 BFKBHPVGDFWCCR-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 239000000556 agonist Substances 0.000 description 6
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- OFVNPOZRBPSFSH-UHFFFAOYSA-N 5-fluoro-1,3-dihydroinden-2-one Chemical compound FC1=CC=C2CC(=O)CC2=C1 OFVNPOZRBPSFSH-UHFFFAOYSA-N 0.000 description 5
- 241000700199 Cavia porcellus Species 0.000 description 5
- 239000005557 antagonist Substances 0.000 description 5
- 239000000872 buffer Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000001530 fumaric acid Substances 0.000 description 5
- UMJJFEIKYGFCAT-UHFFFAOYSA-N indan-2-one Chemical compound C1=CC=C2CC(=O)CC2=C1 UMJJFEIKYGFCAT-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
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- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 238000002224 dissection Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 210000001320 hippocampus Anatomy 0.000 description 1
- 210000003284 horn Anatomy 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- AKQZEFRALAUBFS-UHFFFAOYSA-N ilamine Natural products COC(C)C(O)(C(=O)OCC1=CCN2CCCC12)C(C)(C)O AKQZEFRALAUBFS-UHFFFAOYSA-N 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000013011 mating Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- SJDSHRODCYHDIP-UHFFFAOYSA-N methyl 1-oxa-4-thiaspiro[4.5]decane-7-carboxylate Chemical compound C1C(C(=O)OC)CCCC21SCCO2 SJDSHRODCYHDIP-UHFFFAOYSA-N 0.000 description 1
- OBZXAHPZUFVVRI-UHFFFAOYSA-N methyl 2,3-dihydro-1,4-benzoxathiine-5-carboxylate Chemical compound O1CCSC2=C1C=CC=C2C(=O)OC OBZXAHPZUFVVRI-UHFFFAOYSA-N 0.000 description 1
- 229940120152 methyl 3-hydroxybenzoate Drugs 0.000 description 1
- OXQRLBFDJMSRMM-UHFFFAOYSA-N methyl 3-hydroxycyclohexane-1-carboxylate Chemical compound COC(=O)C1CCCC(O)C1 OXQRLBFDJMSRMM-UHFFFAOYSA-N 0.000 description 1
- MAEFSJWFUPHVPY-UHFFFAOYSA-N methyl 3-oxocyclohexane-1-carboxylate Chemical compound COC(=O)C1CCCC(=O)C1 MAEFSJWFUPHVPY-UHFFFAOYSA-N 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- AYTAYKXVFZPRAF-KQQUZDAGSA-N n'-[(e)-dimethylaminomethylideneamino]-n,n-dimethylmethanimidamide Chemical compound CN(C)\C=N\N=C\N(C)C AYTAYKXVFZPRAF-KQQUZDAGSA-N 0.000 description 1
- MIJBHSBEKPGHDQ-UHFFFAOYSA-N n-(3h-cyclopenta[f][2,1,3]benzoxadiazol-6-yl)acetamide Chemical compound C=1C2=NONC2=CC2=CC(NC(=O)C)=CC2=1 MIJBHSBEKPGHDQ-UHFFFAOYSA-N 0.000 description 1
- IBQMBDAOKKRUDX-UHFFFAOYSA-N n-(5-amino-2,3-dihydro-1h-inden-2-yl)acetamide Chemical compound C1=C(N)C=C2CC(NC(=O)C)CC2=C1 IBQMBDAOKKRUDX-UHFFFAOYSA-N 0.000 description 1
- HMTMYYKVAGYEEW-UHFFFAOYSA-N n-(5-amino-6-nitro-2,3-dihydro-1h-inden-2-yl)acetamide Chemical compound NC1=C([N+]([O-])=O)C=C2CC(NC(=O)C)CC2=C1 HMTMYYKVAGYEEW-UHFFFAOYSA-N 0.000 description 1
- OCRMQBFUELEDCA-UHFFFAOYSA-N n-[1-(3,4-dihydro-2h-chromen-8-yl)piperidin-4-ylidene]hydroxylamine Chemical compound C1CC(=NO)CCN1C1=CC=CC2=C1OCCC2 OCRMQBFUELEDCA-UHFFFAOYSA-N 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 230000001272 neurogenic effect Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 230000003040 nociceptive effect Effects 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- FECKHSTWGKTQAN-UHFFFAOYSA-N pentan-1-amine;hydrobromide Chemical compound [Br-].CCCCC[NH3+] FECKHSTWGKTQAN-UHFFFAOYSA-N 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical group NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 description 1
- LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical compound C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- AIMUHNZKNFEZSN-UHFFFAOYSA-M sodium;decane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCS([O-])(=O)=O AIMUHNZKNFEZSN-UHFFFAOYSA-M 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 201000009032 substance abuse Diseases 0.000 description 1
- 231100000736 substance abuse Toxicity 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- ZCDQUMICDAFZJZ-UHFFFAOYSA-N tert-butyl n-(3,4-dihydro-2h-thiochromen-8-yl)carbamate Chemical compound C1CCSC2=C1C=CC=C2NC(=O)OC(C)(C)C ZCDQUMICDAFZJZ-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
- 238000010361 transduction Methods 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 210000003901 trigeminal nerve Anatomy 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Anesthesiology (AREA)
- Child & Adolescent Psychology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9702360 | 1997-02-27 | ||
| FR9702360A FR2760014B1 (fr) | 1997-02-27 | 1997-02-27 | Nouveaux composes de 2-amino indane, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH10237071A true JPH10237071A (ja) | 1998-09-08 |
| JPH10237071A5 JPH10237071A5 (enExample) | 2005-08-04 |
Family
ID=9504253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10042716A Pending JPH10237071A (ja) | 1997-02-27 | 1998-02-25 | 新規２−アミノインダン化合物、その製造法、及びそれらを含有する医薬組成物 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5968954A (enExample) |
| EP (1) | EP0861837B1 (enExample) |
| JP (1) | JPH10237071A (enExample) |
| CN (1) | CN1090627C (enExample) |
| AT (1) | ATE265451T1 (enExample) |
| AU (1) | AU725756B2 (enExample) |
| BR (1) | BR9800763A (enExample) |
| CA (1) | CA2231025C (enExample) |
| DE (1) | DE69823411T2 (enExample) |
| DK (1) | DK0861837T3 (enExample) |
| ES (1) | ES2219853T3 (enExample) |
| FR (1) | FR2760014B1 (enExample) |
| HU (1) | HU224312B1 (enExample) |
| NO (1) | NO314307B1 (enExample) |
| NZ (1) | NZ329853A (enExample) |
| PL (1) | PL190240B1 (enExample) |
| PT (1) | PT861837E (enExample) |
| ZA (1) | ZA981680B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002534521A (ja) * | 1999-01-12 | 2002-10-15 | ビーエーエスエフ アクチェンゲゼルシャフト | ドーパミン−３−レセプター親和性を有するトリアゾール化合物 |
| WO2006062063A1 (ja) * | 2004-12-08 | 2006-06-15 | Astellas Pharma Inc. | ピペリジン誘導体及びその製造法 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4280067B2 (ja) | 2001-01-16 | 2009-06-17 | アストラゼネカ・アクチエボラーグ | 治療用ヘテロ環式化合物 |
| SE0103650D0 (sv) * | 2001-11-01 | 2001-11-01 | Astrazeneca Ab | Therapeutic heterocyclic compounds |
| AU2002322539B2 (en) | 2001-07-20 | 2007-09-27 | Psychogenics Inc. | Treatment for attention-deficit hyperactivity disorder |
| JP2005343790A (ja) * | 2002-05-31 | 2005-12-15 | Ajinomoto Co Inc | カルシウムチャネル拮抗薬を含有する医薬組成物 |
| US20050165025A1 (en) * | 2004-01-22 | 2005-07-28 | Recordati Ireland Ltd. | Combination therapy with 5HT 1A and 5HT 1B-receptor antagonists |
| UY29892A1 (es) * | 2005-11-04 | 2007-06-29 | Astrazeneca Ab | Nuevos derivados de cromano, composiciones farmaceuticas conteniendolos, procesos de preparacion y aplicaciones |
| WO2020183011A1 (en) | 2019-03-14 | 2020-09-17 | Institut Curie | Htr1d inhibitors and uses thereof in the treatment of cancer |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9318431D0 (en) * | 1993-09-06 | 1993-10-20 | Boots Co Plc | Therapeutic agents |
| FR2734819B1 (fr) * | 1995-05-31 | 1997-07-04 | Adir | Nouveaux composes de la piperazine, de la piperidine et de la 1,2,5,6-tetrahydropyridine, leur procede de preparation et les compositions pharmaceutiques les contenant |
-
1997
- 1997-02-27 FR FR9702360A patent/FR2760014B1/fr not_active Expired - Fee Related
-
1998
- 1998-02-24 PL PL98324982A patent/PL190240B1/pl not_active IP Right Cessation
- 1998-02-25 JP JP10042716A patent/JPH10237071A/ja active Pending
- 1998-02-25 BR BR9800763-7A patent/BR9800763A/pt not_active Application Discontinuation
- 1998-02-26 NZ NZ329853A patent/NZ329853A/xx unknown
- 1998-02-26 US US09/031,490 patent/US5968954A/en not_active Expired - Fee Related
- 1998-02-26 HU HU9800422A patent/HU224312B1/hu not_active IP Right Cessation
- 1998-02-26 CN CN98107709A patent/CN1090627C/zh not_active Expired - Fee Related
- 1998-02-26 CA CA002231025A patent/CA2231025C/fr not_active Expired - Fee Related
- 1998-02-26 NO NO19980803A patent/NO314307B1/no unknown
- 1998-02-27 PT PT98400469T patent/PT861837E/pt unknown
- 1998-02-27 AU AU56359/98A patent/AU725756B2/en not_active Ceased
- 1998-02-27 AT AT98400469T patent/ATE265451T1/de not_active IP Right Cessation
- 1998-02-27 ES ES98400469T patent/ES2219853T3/es not_active Expired - Lifetime
- 1998-02-27 DE DE69823411T patent/DE69823411T2/de not_active Expired - Fee Related
- 1998-02-27 EP EP98400469A patent/EP0861837B1/fr not_active Expired - Lifetime
- 1998-02-27 DK DK98400469T patent/DK0861837T3/da active
- 1998-02-27 ZA ZA981680A patent/ZA981680B/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002534521A (ja) * | 1999-01-12 | 2002-10-15 | ビーエーエスエフ アクチェンゲゼルシャフト | ドーパミン−３−レセプター親和性を有するトリアゾール化合物 |
| WO2006062063A1 (ja) * | 2004-12-08 | 2006-06-15 | Astellas Pharma Inc. | ピペリジン誘導体及びその製造法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0861837B1 (fr) | 2004-04-28 |
| CN1090627C (zh) | 2002-09-11 |
| AU5635998A (en) | 1998-09-03 |
| CA2231025A1 (fr) | 1998-08-27 |
| NO980803D0 (no) | 1998-02-26 |
| DE69823411T2 (de) | 2005-02-17 |
| DK0861837T3 (da) | 2004-08-16 |
| PT861837E (pt) | 2004-07-30 |
| HU224312B1 (hu) | 2005-07-28 |
| HK1014945A1 (en) | 1999-10-08 |
| AU725756B2 (en) | 2000-10-19 |
| BR9800763A (pt) | 1999-12-07 |
| ZA981680B (en) | 1998-09-04 |
| ATE265451T1 (de) | 2004-05-15 |
| US5968954A (en) | 1999-10-19 |
| DE69823411D1 (de) | 2004-06-03 |
| PL324982A1 (en) | 1998-08-31 |
| HU9800422D0 (en) | 1998-04-28 |
| ES2219853T3 (es) | 2004-12-01 |
| NO314307B1 (no) | 2003-03-03 |
| NZ329853A (en) | 1999-01-28 |
| HUP9800422A1 (hu) | 1999-12-28 |
| FR2760014B1 (fr) | 1999-04-09 |
| FR2760014A1 (fr) | 1998-08-28 |
| EP0861837A1 (fr) | 1998-09-02 |
| CN1194983A (zh) | 1998-10-07 |
| NO980803L (no) | 1998-08-28 |
| CA2231025C (fr) | 2003-09-16 |
| PL190240B1 (pl) | 2005-11-30 |
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