CA1093558A - 3-benzoyl-or thenoyl-1-[1-(indole-3-ylmethyl) piperid-4-yl] urea compounds - Google Patents
3-benzoyl-or thenoyl-1-[1-(indole-3-ylmethyl) piperid-4-yl] urea compoundsInfo
- Publication number
- CA1093558A CA1093558A CA315,936A CA315936A CA1093558A CA 1093558 A CA1093558 A CA 1093558A CA 315936 A CA315936 A CA 315936A CA 1093558 A CA1093558 A CA 1093558A
- Authority
- CA
- Canada
- Prior art keywords
- acid addition
- piperid
- addition salt
- ylmethyl
- indol
- 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.)
- Expired
Links
- 150000003672 ureas Chemical class 0.000 title 1
- 239000002253 acid Substances 0.000 claims abstract description 35
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 239000001301 oxygen Substances 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 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 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000005864 Sulphur Substances 0.000 claims abstract description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 5
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims abstract description 3
- 125000005059 halophenyl group Chemical group 0.000 claims abstract description 3
- 125000001544 thienyl group Chemical group 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims description 76
- 238000000034 method Methods 0.000 claims description 38
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 31
- 230000008569 process Effects 0.000 claims description 30
- 239000000126 substance Substances 0.000 claims description 16
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 11
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 11
- 239000007858 starting material Substances 0.000 claims description 10
- -1 2- thenyl Chemical group 0.000 claims description 7
- LBRHJTCPPZIPJU-UHFFFAOYSA-N n-[[1-(1h-indol-3-ylmethyl)piperidin-4-yl]carbamoyl]benzamide Chemical compound C1CN(CC=2C3=CC=CC=C3NC=2)CCC1NC(=O)NC(=O)C1=CC=CC=C1 LBRHJTCPPZIPJU-UHFFFAOYSA-N 0.000 claims description 7
- DORQYOMATSPLBB-UHFFFAOYSA-N n-[[1-(1h-indol-3-ylmethyl)piperidin-4-yl]carbamoyl]thiophene-2-carboxamide Chemical compound C1CN(CC=2C3=CC=CC=C3NC=2)CCC1NC(=O)NC(=O)C1=CC=CS1 DORQYOMATSPLBB-UHFFFAOYSA-N 0.000 claims description 5
- 150000002475 indoles Chemical class 0.000 claims description 4
- VKEURNDOWDDXJE-UHFFFAOYSA-N 1-(1h-indol-3-ylmethyl)piperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CNC2=CC=CC=C12 VKEURNDOWDDXJE-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- LMIQERWZRIFWNZ-UHFFFAOYSA-N 5-hydroxyindole Chemical compound OC1=CC=C2NC=CC2=C1 LMIQERWZRIFWNZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- VMISGTWVIOPFHG-UHFFFAOYSA-N n-(piperidin-4-ylcarbamoyl)thiophene-2-carboxamide Chemical compound C=1C=CSC=1C(=O)NC(=O)NC1CCNCC1 VMISGTWVIOPFHG-UHFFFAOYSA-N 0.000 claims description 2
- 150000003053 piperidines Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 6
- IMOPPMCSOORQQL-UHFFFAOYSA-N n-[[1-(1h-indol-3-ylmethyl)piperidin-4-yl]carbamothioyl]benzamide Chemical compound C1CN(CC=2C3=CC=CC=C3NC=2)CCC1NC(=S)NC(=O)C1=CC=CC=C1 IMOPPMCSOORQQL-UHFFFAOYSA-N 0.000 claims 4
- OSIMCAOYIPTHRJ-UHFFFAOYSA-N n-[[1-(1h-indol-3-ylmethyl)piperidin-4-yl]carbamoyl]-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC(=O)NC1CCN(CC=2C3=CC=CC=C3NC=2)CC1 OSIMCAOYIPTHRJ-UHFFFAOYSA-N 0.000 claims 4
- DFIMLIHBLOMGIT-UHFFFAOYSA-N n-[[1-[(5-hydroxy-1h-indol-3-yl)methyl]piperidin-4-yl]carbamoyl]benzamide Chemical compound C12=CC(O)=CC=C2NC=C1CN(CC1)CCC1NC(=O)NC(=O)C1=CC=CC=C1 DFIMLIHBLOMGIT-UHFFFAOYSA-N 0.000 claims 4
- HDUKXVYKQVUFIM-UHFFFAOYSA-N n-[[1-(1h-indol-3-ylmethyl)piperidin-4-yl]carbamoyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC(=O)NC2CCN(CC=3C4=CC=CC=C4NC=3)CC2)=C1 HDUKXVYKQVUFIM-UHFFFAOYSA-N 0.000 claims 2
- QYZRAQWAPAVZAX-UHFFFAOYSA-N n-[[1-[(5-methoxy-1h-indol-3-yl)methyl]piperidin-4-yl]carbamoyl]benzamide Chemical compound C12=CC(OC)=CC=C2NC=C1CN(CC1)CCC1NC(=O)NC(=O)C1=CC=CC=C1 QYZRAQWAPAVZAX-UHFFFAOYSA-N 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- OLKFDXNJEKJUPQ-UHFFFAOYSA-N 4-methoxy-n-(piperidin-4-ylcarbamoyl)benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC(=O)NC1CCNCC1 OLKFDXNJEKJUPQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 101100440695 Dictyostelium discoideum corB gene Proteins 0.000 claims 1
- CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- SKJJGBRWKOFYAD-UHFFFAOYSA-N piperidin-1-ylurea Chemical compound NC(=O)NN1CCCCC1 SKJJGBRWKOFYAD-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 3
- 230000000506 psychotropic effect Effects 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 14
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 14
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 12
- 238000001914 filtration Methods 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 241000700159 Rattus Species 0.000 description 8
- 239000004202 carbamide Substances 0.000 description 8
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 230000003276 anti-hypertensive effect Effects 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 5
- 229960004801 imipramine Drugs 0.000 description 5
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 5
- 239000008194 pharmaceutical composition Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 206010020772 Hypertension Diseases 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 210000004556 brain Anatomy 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 230000001631 hypertensive effect Effects 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229960002748 norepinephrine Drugs 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
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- 230000005764 inhibitory process Effects 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 230000037023 motor activity Effects 0.000 description 3
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 3
- 230000013275 serotonin uptake Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
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- 208000001953 Hypotension Diseases 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
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- 230000021824 exploration behavior Effects 0.000 description 2
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- 208000021822 hypotensive Diseases 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VDPTZNWSWWZWNC-UHFFFAOYSA-N n-(piperidin-4-ylcarbamoyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(=O)NC1CCNCC1 VDPTZNWSWWZWNC-UHFFFAOYSA-N 0.000 description 2
- 230000012154 norepinephrine uptake Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 2
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- PTXUQNIWGAIHKY-UHFFFAOYSA-N 3-methoxy-n-(piperidin-4-ylcarbamoyl)benzamide Chemical compound COC1=CC=CC(C(=O)NC(=O)NC2CCNCC2)=C1 PTXUQNIWGAIHKY-UHFFFAOYSA-N 0.000 description 1
- GMTDTFQBVHLRCF-UHFFFAOYSA-N 4-fluoro-n-(piperidin-4-ylcarbamoyl)benzamide Chemical compound C1=CC(F)=CC=C1C(=O)NC(=O)NC1CCNCC1 GMTDTFQBVHLRCF-UHFFFAOYSA-N 0.000 description 1
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 1
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
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- 239000003814 drug Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000013284 inhibition of norepinephrine uptake Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 229960001708 magnesium carbonate Drugs 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 230000003547 miosis Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003982 neuronal uptake Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000036963 noncompetitive effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000001242 postsynaptic effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 201000003004 ptosis Diseases 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB50053/77A GB1586817A (en) | 1977-12-01 | 1977-12-01 | Indole derivatives |
| GB50053/77 | 1978-05-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1093558A true CA1093558A (en) | 1981-01-13 |
Family
ID=10454471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA315,936A Expired CA1093558A (en) | 1977-12-01 | 1978-11-07 | 3-benzoyl-or thenoyl-1-[1-(indole-3-ylmethyl) piperid-4-yl] urea compounds |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4209521A (en, 2012) |
| EP (1) | EP0002886B1 (en, 2012) |
| JP (1) | JPS5585586A (en, 2012) |
| AT (1) | AT365591B (en, 2012) |
| AU (1) | AU516185B2 (en, 2012) |
| CA (1) | CA1093558A (en, 2012) |
| DE (1) | DE2861179D1 (en, 2012) |
| DK (1) | DK513678A (en, 2012) |
| ES (4) | ES475565A1 (en, 2012) |
| FI (1) | FI783473A7 (en, 2012) |
| GB (1) | GB1586817A (en, 2012) |
| HU (1) | HU179361B (en, 2012) |
| IE (1) | IE47461B1 (en, 2012) |
| IT (1) | IT1100596B (en, 2012) |
| NZ (1) | NZ188773A (en, 2012) |
| PH (1) | PH19933A (en, 2012) |
| PT (1) | PT68850A (en, 2012) |
| SU (4) | SU1042612A3 (en, 2012) |
| YU (1) | YU280378A (en, 2012) |
| ZA (1) | ZA786058B (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL128510B1 (en) * | 1980-03-01 | 1984-02-29 | Wyeth John & Brother Ltd | Method of obtaining new piperidine derivatives |
| US4806552A (en) * | 1980-03-01 | 1989-02-21 | John Wyeth & Brother, Limited | Pyridyl- and/or pyridoyl-(piperid-4-yl) ureas and analogues thereof |
| US4722930A (en) * | 1980-03-01 | 1988-02-02 | John Wyeth And Brother Limited | 3-benzoyl-1-[(oxo or thioheteroaryl-ylalkyl)-piperid-4-yl]ureas and derivatives |
| US4808601A (en) * | 1984-09-19 | 1989-02-28 | Pfizer Inc. | Analgesic and antiinflammatory 1,3-diacyl-2-oxindole compounds |
| US4752609A (en) * | 1985-06-20 | 1988-06-21 | Pfizer Inc. | Analgesic and antiinflammatory 1,3-diacyl-2-oxindole compounds |
| GB8528234D0 (en) * | 1985-11-15 | 1985-12-18 | Wyeth John & Brother Ltd | Heterocyclic compounds |
| US20070021355A1 (en) * | 2003-05-29 | 2007-01-25 | Hiroaki Kohno | Antidepressants or foods and beverage for antidepression |
| AR070398A1 (es) * | 2008-02-22 | 2010-03-31 | Gruenenthal Chemie | Derivados sustituidos de indol |
| MX2020004842A (es) * | 2017-11-03 | 2020-10-16 | Bioimics Ab | Compuestos heterociclicos antiinfecciosos y sus usos. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1494805A (en) * | 1975-07-17 | 1977-12-14 | Wyeth John & Brother Ltd | Indole derivatives |
| US4061641A (en) * | 1973-10-10 | 1977-12-06 | John Wyeth & Brother Limited | Ureidopiperidino-ketoalkyl indoles |
| GB1425354A (en) * | 1973-10-10 | 1976-02-18 | Wyeth John & Brother Ltd | Indole derivatives |
| ZA76475B (en) * | 1975-03-10 | 1977-08-31 | Ciba Geigy Ag | Indolyalkylpiperidines |
-
1977
- 1977-12-01 GB GB50053/77A patent/GB1586817A/en not_active Expired
-
1978
- 1978-10-24 IE IE2100/78A patent/IE47461B1/en unknown
- 1978-10-26 ZA ZA786058A patent/ZA786058B/xx unknown
- 1978-10-30 NZ NZ188773A patent/NZ188773A/xx unknown
- 1978-11-01 AU AU41231/78A patent/AU516185B2/en not_active Expired
- 1978-11-07 CA CA315,936A patent/CA1093558A/en not_active Expired
- 1978-11-08 US US05/958,763 patent/US4209521A/en not_active Expired - Lifetime
- 1978-11-14 FI FI783473A patent/FI783473A7/fi unknown
- 1978-11-17 DK DK513678A patent/DK513678A/da not_active Application Discontinuation
- 1978-11-20 PH PH21825A patent/PH19933A/en unknown
- 1978-11-21 DE DE7878300651T patent/DE2861179D1/de not_active Expired
- 1978-11-21 EP EP78300651A patent/EP0002886B1/en not_active Expired
- 1978-11-23 IT IT30109/78A patent/IT1100596B/it active
- 1978-11-28 YU YU02803/78A patent/YU280378A/xx unknown
- 1978-11-29 HU HU78WI297A patent/HU179361B/hu unknown
- 1978-11-29 AT AT0853578A patent/AT365591B/de not_active IP Right Cessation
- 1978-11-29 SU SU782692750A patent/SU1042612A3/ru active
- 1978-11-30 JP JP14734578A patent/JPS5585586A/ja active Granted
- 1978-11-30 PT PT68850A patent/PT68850A/pt unknown
- 1978-11-30 ES ES475565A patent/ES475565A1/es not_active Expired
-
1979
- 1979-05-16 ES ES480603A patent/ES480603A1/es not_active Expired
- 1979-05-16 ES ES480604A patent/ES480604A1/es not_active Expired
- 1979-05-16 ES ES480602A patent/ES480602A1/es not_active Expired
- 1979-12-18 SU SU792852306A patent/SU1087073A3/ru active
-
1980
- 1980-01-04 SU SU802862505A patent/SU1110380A3/ru active
- 1980-01-07 SU SU802864113A patent/SU1083910A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| SU1110380A3 (ru) | 1984-08-23 |
| ZA786058B (en) | 1980-05-28 |
| AU516185B2 (en) | 1981-05-21 |
| AU4123178A (en) | 1979-06-07 |
| IT7830109A0 (it) | 1978-11-23 |
| SU1087073A3 (ru) | 1984-04-15 |
| EP0002886A2 (en) | 1979-07-11 |
| DE2861179D1 (en) | 1981-12-24 |
| SU1042612A3 (ru) | 1983-09-15 |
| IE47461B1 (en) | 1984-03-21 |
| IT1100596B (it) | 1985-09-28 |
| ES480604A1 (es) | 1980-04-01 |
| HU179361B (en) | 1982-10-28 |
| EP0002886A3 (en) | 1979-07-25 |
| PT68850A (en) | 1978-12-01 |
| DK513678A (da) | 1979-06-02 |
| SU1083910A3 (ru) | 1984-03-30 |
| GB1586817A (en) | 1981-03-25 |
| ES480602A1 (es) | 1980-04-01 |
| ATA853578A (de) | 1981-06-15 |
| US4209521A (en) | 1980-06-24 |
| FI783473A7 (fi) | 1979-06-02 |
| YU280378A (en) | 1983-01-21 |
| NZ188773A (en) | 1981-03-16 |
| ES475565A1 (es) | 1980-01-16 |
| PH19933A (en) | 1986-08-14 |
| AT365591B (de) | 1982-01-25 |
| IE782100L (en) | 1979-06-01 |
| JPS6257606B2 (en, 2012) | 1987-12-02 |
| EP0002886B1 (en) | 1981-10-14 |
| ES480603A1 (es) | 1980-04-01 |
| JPS5585586A (en) | 1980-06-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |