CH672787A5 - - Google Patents
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- Publication number
- CH672787A5 CH672787A5 CH1830/86A CH183086A CH672787A5 CH 672787 A5 CH672787 A5 CH 672787A5 CH 1830/86 A CH1830/86 A CH 1830/86A CH 183086 A CH183086 A CH 183086A CH 672787 A5 CH672787 A5 CH 672787A5
- Authority
- CH
- Switzerland
- Prior art keywords
- radical
- piperazinyl
- compound
- lower alkyl
- hydrogen atom
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 155
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 34
- -1 Furo [3,2-c] pyridin-4-yl Chemical group 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 11
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 5
- 239000010452 phosphate Substances 0.000 claims description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 208000028017 Psychotic disease Diseases 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
- 239000012279 sodium borohydride Substances 0.000 claims description 2
- 238000007910 systemic administration Methods 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- LIODOFLHMDNDLV-UHFFFAOYSA-N 1,1-dioxo-2-[4-(4-thieno[3,2-c]pyridin-4-ylpiperazin-1-yl)butyl]-1,2-benzothiazol-3-one Chemical compound O=S1(=O)C2=CC=CC=C2C(=O)N1CCCCN1CCN(C=2C=3C=CSC=3C=CN=2)CC1 LIODOFLHMDNDLV-UHFFFAOYSA-N 0.000 claims 1
- ZJYWNDXQKAEZJP-UHFFFAOYSA-N 1-[4-[4-(2-bromothieno[3,2-c]pyridin-4-yl)piperazin-1-yl]butyl]-4,4-dimethylpiperidine-2,6-dione Chemical compound O=C1CC(C)(C)CC(=O)N1CCCCN1CCN(C=2C=3C=C(Br)SC=3C=CN=2)CC1 ZJYWNDXQKAEZJP-UHFFFAOYSA-N 0.000 claims 1
- ORDSVYXFMRRIFU-UHFFFAOYSA-N 3-[4-[4-(1-methylpyrrolo[3,2-c]pyridin-4-yl)piperazin-1-yl]butyl]-1-thia-3-azaspiro[4.4]nonane-2,4-dione Chemical compound N1=CC=C2N(C)C=CC2=C1N(CC1)CCN1CCCCN(C1=O)C(=O)SC21CCCC2 ORDSVYXFMRRIFU-UHFFFAOYSA-N 0.000 claims 1
- DRRBJWHZVHKSCN-UHFFFAOYSA-N 3-[4-[4-(2-bromothieno[3,2-c]pyridin-4-yl)piperazin-1-yl]butyl]-1-thia-3-azaspiro[4.4]nonane-2,4-dione Chemical compound N1=CC=C2SC(Br)=CC2=C1N(CC1)CCN1CCCCN(C1=O)C(=O)SC21CCCC2 DRRBJWHZVHKSCN-UHFFFAOYSA-N 0.000 claims 1
- XKTCRHODWQUSIJ-UHFFFAOYSA-N 3-[4-[4-(2-methylfuro[3,2-c]pyridin-4-yl)piperazin-1-yl]butyl]-1-thia-3-azaspiro[4.4]nonane-2,4-dione Chemical compound N1=CC=C2OC(C)=CC2=C1N(CC1)CCN1CCCCN(C1=O)C(=O)SC21CCCC2 XKTCRHODWQUSIJ-UHFFFAOYSA-N 0.000 claims 1
- FGRXOPGLGIJRPW-UHFFFAOYSA-N 3-[4-[4-(2-methylthieno[3,2-c]pyridin-4-yl)piperazin-1-yl]butyl]-1-thia-3-azaspiro[4.4]nonane-2,4-dione Chemical compound N1=CC=C2SC(C)=CC2=C1N(CC1)CCN1CCCCN(C1=O)C(=O)SC21CCCC2 FGRXOPGLGIJRPW-UHFFFAOYSA-N 0.000 claims 1
- GMZNQMSZVPCDLB-UHFFFAOYSA-N 4,4-dimethyl-1-[4-[4-(1-methylpyrrolo[3,2-c]pyridin-4-yl)piperazin-1-yl]butyl]piperidine-2,6-dione Chemical compound N1=CC=C2N(C)C=CC2=C1N(CC1)CCN1CCCCN1C(=O)CC(C)(C)CC1=O GMZNQMSZVPCDLB-UHFFFAOYSA-N 0.000 claims 1
- RLIZPUXPCGFMOI-UHFFFAOYSA-N 4,4-dimethyl-1-[4-[4-(2-methylfuro[3,2-c]pyridin-4-yl)piperazin-1-yl]butyl]piperidine-2,6-dione Chemical compound N1=CC=C2OC(C)=CC2=C1N(CC1)CCN1CCCCN1C(=O)CC(C)(C)CC1=O RLIZPUXPCGFMOI-UHFFFAOYSA-N 0.000 claims 1
- UFCKXALAMVSRPD-UHFFFAOYSA-N 4-[4-(4-thieno[3,2-c]pyridin-4-ylpiperazin-1-yl)butyl]morpholine-3,5-dione Chemical compound O=C1COCC(=O)N1CCCCN1CCN(C=2C=3C=CSC=3C=CN=2)CC1 UFCKXALAMVSRPD-UHFFFAOYSA-N 0.000 claims 1
- XTONORBIIMZXAJ-UHFFFAOYSA-N 4-[4-(4-thieno[3,2-c]pyridin-4-ylpiperazin-1-yl)butyl]thiomorpholine-3,5-dione Chemical compound O=C1CSCC(=O)N1CCCCN1CCN(C=2C=3C=CSC=3C=CN=2)CC1 XTONORBIIMZXAJ-UHFFFAOYSA-N 0.000 claims 1
- LMCWHRGQHKPHCK-UHFFFAOYSA-N 4-[4-[4-(1-methylpyrrolo[3,2-c]pyridin-4-yl)piperazin-1-yl]butyl]morpholine-3,5-dione Chemical compound N1=CC=C2N(C)C=CC2=C1N(CC1)CCN1CCCCN1C(=O)COCC1=O LMCWHRGQHKPHCK-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 150000001805 chlorine compounds Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- PYEZYNAHBMWJFR-UHFFFAOYSA-N thieno[3,2-c]pyridine Chemical compound N1=CC=C2S[C]=CC2=C1 PYEZYNAHBMWJFR-UHFFFAOYSA-N 0.000 claims 1
- 239000000543 intermediate Substances 0.000 description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- 230000000561 anti-psychotic effect Effects 0.000 description 12
- 208000009132 Catalepsy Diseases 0.000 description 11
- 206010047853 Waxy flexibility Diseases 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000164 antipsychotic agent Substances 0.000 description 9
- 230000027455 binding Effects 0.000 description 9
- 230000000701 neuroleptic effect Effects 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000003176 neuroleptic agent Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- RVGRTFBJOXMFAX-UHFFFAOYSA-N 4-piperazin-1-ylthieno[3,2-c]pyridine Chemical compound C1CNCCN1C1=NC=CC2=C1C=CS2 RVGRTFBJOXMFAX-UHFFFAOYSA-N 0.000 description 7
- 210000003169 central nervous system Anatomy 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000000506 psychotropic effect Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 229940005529 antipsychotics Drugs 0.000 description 6
- 125000002619 bicyclic group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000008177 pharmaceutical agent Substances 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- DUPNPBCUJHMSFZ-UHFFFAOYSA-N 5h-thieno[3,2-c]pyridin-4-one Chemical compound O=C1NC=CC2=C1C=CS2 DUPNPBCUJHMSFZ-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 4
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 4
- 229960004170 clozapine Drugs 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000002441 reversible effect Effects 0.000 description 4
- 229940076279 serotonin Drugs 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 3
- 229960004046 apomorphine Drugs 0.000 description 3
- 150000001540 azides Chemical class 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000003291 dopaminomimetic effect Effects 0.000 description 3
- 150000003949 imides Chemical group 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 125000004193 piperazinyl group Chemical group 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000004089 psychotropic agent Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical group C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 3
- 230000002936 tranquilizing effect Effects 0.000 description 3
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical group C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 2
- OUKQTRFCDKSEPL-UHFFFAOYSA-N 1-Methyl-2-pyrrolecarboxaldehyde Chemical compound CN1C=CC=C1C=O OUKQTRFCDKSEPL-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical group OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- VFPFMOXMHVQFNR-UHFFFAOYSA-N 4-chlorothieno[3,2-c]pyridine Chemical compound ClC1=NC=CC2=C1C=CS2 VFPFMOXMHVQFNR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 238000006969 Curtius rearrangement reaction Methods 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- CETBSQOFQKLHHZ-UHFFFAOYSA-N Diethyl disulfide Chemical compound CCSSCC CETBSQOFQKLHHZ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 108050004812 Dopamine receptor Proteins 0.000 description 2
- 102000015554 Dopamine receptor Human genes 0.000 description 2
- 208000027776 Extrapyramidal disease Diseases 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 150000008533 dibenzodiazepines Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73120185A | 1985-05-06 | 1985-05-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH672787A5 true CH672787A5 (enrdf_load_stackoverflow) | 1989-12-29 |
Family
ID=24938510
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1830/86A CH672787A5 (enrdf_load_stackoverflow) | 1985-05-06 | 1986-05-05 |
Country Status (25)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5801186A (en) | 1987-11-20 | 1998-09-01 | Hoechst Marion Roussel, Inc. | 3- 4-(1-substituted-4-piperazinyl)butyl!-4-thiazolidinone and related compounds |
| US4880930A (en) * | 1987-11-30 | 1989-11-14 | New James S | Psychotropic acyclic amide derivatives |
| US4780466A (en) * | 1988-03-17 | 1988-10-25 | Hoechst-Roussel Pharmaceuticals, Inc. | Arylpiperazinylalkoxy derivatives of cyclic imides |
| IE903410A1 (en) * | 1989-10-09 | 1991-04-10 | Novo Nordisk As | Indole derivatives, their preparation and use |
| US5272148A (en) * | 1992-09-09 | 1993-12-21 | Hoechst-Roussel Pharmaceuticals Incorporated | Heteroarenylpiperazines |
| FR2738822B1 (fr) * | 1995-09-15 | 1997-10-31 | Synthelabo | Derives de 4-(omega-(4-(thieno(3,2-c)pyridin-4-yl)piperazin- 1-yl)alkyl)quinolein-2(1h)-one, leur preparation et leur application en therapeutique |
| IL123600A (en) * | 1995-09-15 | 2001-05-20 | Sanofi Synthelabo | History of quinolone - 2 (1H), their preparation and pharmaceutical preparations containing them |
| FR2738823B1 (fr) * | 1995-09-15 | 1997-10-31 | Synthelabo | Derives de 3-(omega-(4-(thieno(3,2-c)pyridin-4-yl)piperazin- 1-yl)alkyl)-3,4-dihydroquinolein-2(1h)-one,leur preparation et leur application en therapeutique |
| FR2738824B1 (fr) * | 1995-09-15 | 1997-10-31 | Synthelabo | Derives de 3-(omega(4-(thieno(3,2-c)pyridin-4-yl)piperazin-1 -yl)alkyl)-3,4-dihydroquinazolin-2(1h)-one,leur preparation et leur application en therapeutique |
| FR2761071B1 (fr) * | 1997-03-20 | 1999-12-03 | Synthelabo | Derives de quinolein-2(1h)-one et de dihydroquinolein-2(1h)- one, leur preparation et leur application en therapeutique |
| FR2797874B1 (fr) * | 1999-08-27 | 2002-03-29 | Adir | Nouveaux derives de la pyridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US20040077605A1 (en) | 2001-06-20 | 2004-04-22 | Salvati Mark E. | Fused heterocyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4367335A (en) * | 1981-08-03 | 1983-01-04 | Mead Johnson & Company | Thiazolidinylalkylene piperazine derivatives |
| US4452799A (en) * | 1981-12-23 | 1984-06-05 | Mead Johnson & Company | Benzisothiazole and benzisoxazole piperazine derivatives |
| US4361565A (en) * | 1981-12-28 | 1982-11-30 | Mead Johnson & Company | 2-[4-[(4,4-Dialkyl-2,6-piperidinedion-1-yl)butyl]-1-piperazinyl]pyridines |
-
1986
- 1986-03-11 CA CA000503794A patent/CA1278792C/en not_active Expired - Fee Related
- 1986-03-19 ZA ZA862046A patent/ZA862046B/xx unknown
- 1986-04-29 EG EG250/86A patent/EG18206A/xx active
- 1986-04-29 GR GR861149A patent/GR861149B/el unknown
- 1986-04-29 AU AU56795/86A patent/AU593244B2/en not_active Expired
- 1986-04-30 FI FI861820A patent/FI85484C/fi not_active IP Right Cessation
- 1986-05-02 KR KR1019860003445A patent/KR940000829B1/ko not_active Expired - Fee Related
- 1986-05-02 GB GB08610810A patent/GB2174703B/en not_active Expired
- 1986-05-05 CN CN86103071A patent/CN1017901B/zh not_active Expired
- 1986-05-05 NL NL8601146A patent/NL8601146A/nl active Search and Examination
- 1986-05-05 IE IE119386A patent/IE59201B1/en not_active IP Right Cessation
- 1986-05-05 SE SE8602061A patent/SE465270B/sv not_active IP Right Cessation
- 1986-05-05 ES ES554659A patent/ES8801250A1/es not_active Expired
- 1986-05-05 CH CH1830/86A patent/CH672787A5/de not_active IP Right Cessation
- 1986-05-05 LU LU86421A patent/LU86421A1/fr unknown
- 1986-05-05 DE DE3615180A patent/DE3615180C2/de not_active Expired - Lifetime
- 1986-05-05 FR FR8606471A patent/FR2581385B1/fr not_active Expired - Lifetime
- 1986-05-05 DK DK207186A patent/DK165745C/da not_active IP Right Cessation
- 1986-05-05 BE BE0/216623A patent/BE904724A/fr not_active IP Right Cessation
- 1986-05-06 PT PT82523A patent/PT82523B/pt unknown
- 1986-05-06 HU HU861860A patent/HU195509B/hu unknown
- 1986-05-06 JP JP61103726A patent/JPH0753728B2/ja not_active Expired - Lifetime
- 1986-05-06 AT AT0121486A patent/AT398572B/de not_active IP Right Cessation
- 1986-05-06 IT IT8620313A patent/IT1208607B/it active
-
1987
- 1987-09-25 ES ES557757A patent/ES8802149A1/es not_active Expired
- 1987-10-01 MY MYPI87002712A patent/MY100777A/en unknown
-
1988
- 1988-01-28 ES ES557809A patent/ES8802614A1/es not_active Expired
- 1988-05-26 ES ES557839A patent/ES8900138A1/es not_active Expired
- 1988-11-16 ES ES557855A patent/ES8900253A1/es not_active Expired
-
1989
- 1989-02-27 ES ES557865A patent/ES9000005A1/es not_active Expired
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