CA1085852A - 1,3-dihydro-1- 3-(1-piperidinyl)propyl -2h- benzimidazol-2-ones and related compounds - Google Patents
1,3-dihydro-1- 3-(1-piperidinyl)propyl -2h- benzimidazol-2-ones and related compoundsInfo
- Publication number
- CA1085852A CA1085852A CA256,450A CA256450A CA1085852A CA 1085852 A CA1085852 A CA 1085852A CA 256450 A CA256450 A CA 256450A CA 1085852 A CA1085852 A CA 1085852A
- Authority
- CA
- Canada
- Prior art keywords
- dihydro
- group
- benzimidazol
- formula
- parts
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 83
- 150000003053 piperidines Chemical class 0.000 claims abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 25
- 150000002148 esters Chemical group 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- -1 alkali metal isocyanates Chemical class 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 238000003756 stirring Methods 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 6
- FGXWKSZFVQUSTL-UHFFFAOYSA-N domperidone Chemical compound C12=CC=CC=C2NC(=O)N1CCCN(CC1)CCC1N1C2=CC=C(Cl)C=C2NC1=O FGXWKSZFVQUSTL-UHFFFAOYSA-N 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical group NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 5
- GUMPYDGUYXOYML-UHFFFAOYSA-N 3-(3-chloropropyl)-1h-benzimidazol-2-one Chemical compound C1=CC=C2NC(=O)N(CCCCl)C2=C1 GUMPYDGUYXOYML-UHFFFAOYSA-N 0.000 claims description 5
- 230000002152 alkylating effect Effects 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 claims description 2
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 2
- 230000000875 corresponding effect Effects 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- HBFOMEVBPFTLRF-UHFFFAOYSA-N 1-(4-fluorophenyl)-8-[3-(2-oxo-3h-benzimidazol-1-yl)propyl]-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1=CC(F)=CC=C1N1C2(CCN(CCCN3C(NC4=CC=CC=C43)=O)CC2)C(=O)NC1 HBFOMEVBPFTLRF-UHFFFAOYSA-N 0.000 claims 2
- BEEPXSBZGLKIOT-UHFFFAOYSA-N 1-(4-fluorophenyl)-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1=CC(F)=CC=C1N1C2(CCNCC2)C(=O)NC1 BEEPXSBZGLKIOT-UHFFFAOYSA-N 0.000 claims 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000962 organic group Chemical group 0.000 claims 1
- 239000002111 antiemetic agent Substances 0.000 abstract description 4
- 229940125683 antiemetic agent Drugs 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 69
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- 239000000243 solution Substances 0.000 description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 43
- 239000000047 product Substances 0.000 description 40
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 28
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 25
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 229960001701 chloroform Drugs 0.000 description 24
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 23
- 239000007858 starting material Substances 0.000 description 22
- 239000003480 eluent Substances 0.000 description 20
- 238000001816 cooling Methods 0.000 description 15
- 235000017550 sodium carbonate Nutrition 0.000 description 15
- 229910000029 sodium carbonate Inorganic materials 0.000 description 15
- 229940001593 sodium carbonate Drugs 0.000 description 15
- 125000001309 chloro group Chemical group Cl* 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 11
- 239000000284 extract Substances 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 11
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 229960000443 hydrochloric acid Drugs 0.000 description 9
- 235000011167 hydrochloric acid Nutrition 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 229940044613 1-propanol Drugs 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- DOAYWDKFDPSTSV-UHFFFAOYSA-N 5-chloro-1,3-dihydro-1-(4-piperidinyl)-2h-benzimidazol-2-one Chemical compound O=C1NC2=CC(Cl)=CC=C2N1C1CCNCC1 DOAYWDKFDPSTSV-UHFFFAOYSA-N 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 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 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 230000003474 anti-emetic effect Effects 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 229960005335 propanol Drugs 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- ORPVEAJIYCFESN-UHFFFAOYSA-N 1-(3-iodopropyl)-3-methylbenzimidazol-2-one Chemical compound C1=CC=C2N(CCCI)C(=O)N(C)C2=C1 ORPVEAJIYCFESN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- 238000007126 N-alkylation reaction Methods 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 3
- 206010047700 Vomiting Diseases 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000686 essence Substances 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 3
- 239000008213 purified water Substances 0.000 description 3
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 3
- HTQWGIHCFPWKAS-UHFFFAOYSA-N 1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1CNCCC11C(=O)NCN1C1=CC=CC=C1 HTQWGIHCFPWKAS-UHFFFAOYSA-N 0.000 description 2
- PFWYUAAUZLXMFU-UHFFFAOYSA-N 3,4-dihydro-2h-[1,3]oxazino[3,2-a]benzimidazole Chemical compound C1=CC=C2N(CCCO3)C3=NC2=C1 PFWYUAAUZLXMFU-UHFFFAOYSA-N 0.000 description 2
- JYCMQSHPLUEKNM-UHFFFAOYSA-N 3-(3-chloropropyl)-5,6-dimethyl-1h-benzimidazol-2-one Chemical compound C1=C(C)C(C)=CC2=C1N(CCCCl)C(=O)N2 JYCMQSHPLUEKNM-UHFFFAOYSA-N 0.000 description 2
- GTFIPUCJLHMBTP-UHFFFAOYSA-N 3-[3-[4-(2-amino-4-chloroanilino)piperidin-1-yl]propyl]-1h-benzimidazol-2-one Chemical compound NC1=CC(Cl)=CC=C1NC1CCN(CCCN2C(NC3=CC=CC=C32)=O)CC1 GTFIPUCJLHMBTP-UHFFFAOYSA-N 0.000 description 2
- JCSBLJVHXYEXKY-UHFFFAOYSA-N 3-[3-[4-(2-aminoanilino)piperidin-1-yl]propyl]-1h-benzimidazol-2-one Chemical compound NC1=CC=CC=C1NC1CCN(CCCN2C(NC3=CC=CC=C32)=O)CC1 JCSBLJVHXYEXKY-UHFFFAOYSA-N 0.000 description 2
- LGGVWUKOORSGDT-UHFFFAOYSA-N 3-[3-[4-(4-chloro-2-nitroanilino)piperidin-1-yl]propyl]-1h-benzimidazol-2-one Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1NC1CCN(CCCN2C(NC3=CC=CC=C32)=O)CC1 LGGVWUKOORSGDT-UHFFFAOYSA-N 0.000 description 2
- OJKMXTNJSZJNNO-UHFFFAOYSA-N 6-chloro-3-(3-hydroxypropyl)-1h-benzimidazol-2-one;methanesulfonic acid Chemical compound CS(O)(=O)=O.C1=C(Cl)C=C2NC(=O)N(CCCO)C2=C1 OJKMXTNJSZJNNO-UHFFFAOYSA-N 0.000 description 2
- RGCKVXVZECRYAS-UHFFFAOYSA-N 6-chloro-3-[1-[3-(2-nitroanilino)propyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound [O-][N+](=O)C1=CC=CC=C1NCCCN1CCC(N2C(NC3=CC(Cl)=CC=C32)=O)CC1 RGCKVXVZECRYAS-UHFFFAOYSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 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
- 239000001856 Ethyl cellulose Substances 0.000 description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- WZELXJBMMZFDDU-UHFFFAOYSA-N Imidazol-2-one Chemical compound O=C1N=CC=N1 WZELXJBMMZFDDU-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 244000171263 Ribes grossularia Species 0.000 description 2
- 235000002357 Ribes grossularia Nutrition 0.000 description 2
- 235000011034 Rubus glaucus Nutrition 0.000 description 2
- 235000009122 Rubus idaeus Nutrition 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 244000299461 Theobroma cacao Species 0.000 description 2
- 235000009470 Theobroma cacao Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 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 2
- 229960004046 apomorphine Drugs 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 235000019325 ethyl cellulose Nutrition 0.000 description 2
- 229920001249 ethyl cellulose Polymers 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- JFDLNTWOJUPVTD-UHFFFAOYSA-N n-(2-nitrophenyl)piperidin-4-amine Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1CCNCC1 JFDLNTWOJUPVTD-UHFFFAOYSA-N 0.000 description 2
- WOFRVOOYNJVVIK-UHFFFAOYSA-N n-(3-chloropropyl)-2-nitroaniline Chemical compound [O-][N+](=O)C1=CC=CC=C1NCCCCl WOFRVOOYNJVVIK-UHFFFAOYSA-N 0.000 description 2
- XRSHTORJYMIIHI-UHFFFAOYSA-N n-(4-chloro-2-nitrophenyl)piperidin-4-amine;hydrobromide Chemical compound Br.[O-][N+](=O)C1=CC(Cl)=CC=C1NC1CCNCC1 XRSHTORJYMIIHI-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229940100688 oral solution Drugs 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- CSIGAEASXSGNKS-UHFFFAOYSA-N propane-1,1,3-triol Chemical compound OCCC(O)O CSIGAEASXSGNKS-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical class C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- BVDCQSJSEVYRCZ-UHFFFAOYSA-N 1-(3-bromopropyl)benzotriazole Chemical compound C1=CC=C2N(CCCBr)N=NC2=C1 BVDCQSJSEVYRCZ-UHFFFAOYSA-N 0.000 description 1
- SJKDPYFMQPBXPL-UHFFFAOYSA-N 1-(3-chloro-2-methylpropyl)-3-prop-1-en-2-ylbenzimidazol-2-one Chemical compound C1=CC=C2N(C(C)=C)C(=O)N(CC(CCl)C)C2=C1 SJKDPYFMQPBXPL-UHFFFAOYSA-N 0.000 description 1
- YORYLERTCJEGGR-UHFFFAOYSA-N 1-(3-chloropropyl)-3-prop-1-en-2-yl-2h-benzimidazole Chemical compound C1=CC=C2N(C(=C)C)CN(CCCCl)C2=C1 YORYLERTCJEGGR-UHFFFAOYSA-N 0.000 description 1
- MKZOYCWVYJRSAQ-UHFFFAOYSA-N 1-(3-chloropropyl)-3-prop-1-en-2-ylbenzimidazol-2-one Chemical compound C1=CC=C2N(CCCCl)C(=O)N(C(=C)C)C2=C1 MKZOYCWVYJRSAQ-UHFFFAOYSA-N 0.000 description 1
- DJWHEMXXGJGGIX-UHFFFAOYSA-N 1-(3-chloropropyl)-5-methyl-3-prop-1-en-2-ylbenzimidazol-2-one Chemical compound CC1=CC=C2N(CCCCl)C(=O)N(C(=C)C)C2=C1 DJWHEMXXGJGGIX-UHFFFAOYSA-N 0.000 description 1
- ZWPCPESYNXKKPL-UHFFFAOYSA-N 1-(4-chloro-3-methylphenyl)-8-[3-(2-oxo-3h-benzimidazol-1-yl)propyl]-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1=C(Cl)C(C)=CC(N2C3(CCN(CCCN4C(NC5=CC=CC=C54)=O)CC3)C(=O)NC2)=C1 ZWPCPESYNXKKPL-UHFFFAOYSA-N 0.000 description 1
- FUUQVYQMLCHUCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-8-[3-(2-oxo-3h-benzimidazol-1-yl)propyl]-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1=CC(Cl)=CC=C1N1C2(CCN(CCCN3C(NC4=CC=CC=C43)=O)CC2)C(=O)NC1 FUUQVYQMLCHUCY-UHFFFAOYSA-N 0.000 description 1
- BCBRLOHKVLDVSU-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-methyl-8-[3-(2-oxo-3h-benzimidazol-1-yl)propyl]-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1CN(CCCN2C(NC3=CC=CC=C32)=O)CCC21C(=O)N(C)CN2C1=CC=C(F)C=C1 BCBRLOHKVLDVSU-UHFFFAOYSA-N 0.000 description 1
- QSBADBLGWCTOMR-UHFFFAOYSA-N 1-(4-fluorophenyl)-8-[2-methyl-3-(2-oxo-3h-benzimidazol-1-yl)propyl]-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C12=CC=CC=C2NC(=O)N1CC(C)CN(CC1)CCC1(C(NC1)=O)N1C1=CC=C(F)C=C1 QSBADBLGWCTOMR-UHFFFAOYSA-N 0.000 description 1
- OKRBHTGEKIFYHD-UHFFFAOYSA-N 1-[1-[3-(2-oxo-3h-benzimidazol-1-yl)propyl]piperidin-4-yl]-3-propan-2-ylbenzimidazol-2-one Chemical compound C12=CC=CC=C2NC(=O)N1CCCN(CC1)CCC1N1C2=CC=CC=C2N(C(C)C)C1=O OKRBHTGEKIFYHD-UHFFFAOYSA-N 0.000 description 1
- CEFGTTQKEDXYEY-UHFFFAOYSA-N 1-[3-(benzimidazol-1-yl)propyl]-4-(4-chlorophenyl)piperidin-4-ol Chemical compound C1CN(CCCN2C3=CC=CC=C3N=C2)CCC1(O)C1=CC=C(Cl)C=C1 CEFGTTQKEDXYEY-UHFFFAOYSA-N 0.000 description 1
- XSPZXWBRHMTYAZ-UHFFFAOYSA-N 1-[3-[4-(4-chloro-2-nitroanilino)piperidin-1-yl]propyl]-3-prop-1-en-2-ylbenzimidazol-2-one Chemical compound O=C1N(C(=C)C)C2=CC=CC=C2N1CCCN(CC1)CCC1NC1=CC=C(Cl)C=C1[N+]([O-])=O XSPZXWBRHMTYAZ-UHFFFAOYSA-N 0.000 description 1
- VQNZRCMKMSGKDN-UHFFFAOYSA-N 1-[3-[4-(5-chloro-2-oxo-3h-benzimidazol-1-yl)piperidin-1-yl]-2-methylpropyl]-3-prop-1-en-2-ylbenzimidazol-2-one Chemical compound C12=CC=CC=C2N(C(C)=C)C(=O)N1CC(C)CN1CCC(N2C(NC3=CC(Cl)=CC=C32)=O)CC1 VQNZRCMKMSGKDN-UHFFFAOYSA-N 0.000 description 1
- ULNUVACPOOAULN-UHFFFAOYSA-N 1-[3-[4-(5-chloro-2-oxo-3h-benzimidazol-1-yl)piperidin-1-yl]propyl]-3-methylbenzimidazol-2-one Chemical compound C12=CC=C(Cl)C=C2NC(=O)N1C(CC1)CCN1CCCN1C2=CC=CC=C2N(C)C1=O ULNUVACPOOAULN-UHFFFAOYSA-N 0.000 description 1
- GTZGCCQWRCAJIS-UHFFFAOYSA-N 1-[3-[4-(5-chloro-2-oxo-3h-benzimidazol-1-yl)piperidin-1-yl]propyl]-3-prop-1-en-2-ylbenzimidazol-2-one Chemical compound C12=CC=C(Cl)C=C2NC(=O)N1C(CC1)CCN1CCCN1C2=CC=CC=C2N(C(=C)C)C1=O GTZGCCQWRCAJIS-UHFFFAOYSA-N 0.000 description 1
- KNFKOSUMYWPYFU-UHFFFAOYSA-N 1-[3-[4-(5-chloro-2-oxo-3h-benzimidazol-1-yl)piperidin-1-yl]propyl]-5-methyl-3-prop-1-en-2-ylbenzimidazol-2-one Chemical compound C12=CC=C(Cl)C=C2NC(=O)N1C(CC1)CCN1CCCN1C2=CC=C(C)C=C2N(C(=C)C)C1=O KNFKOSUMYWPYFU-UHFFFAOYSA-N 0.000 description 1
- TZGFQIXRVUHDLE-UHFFFAOYSA-N 1-chloro-2-nitro-4-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1Cl TZGFQIXRVUHDLE-UHFFFAOYSA-N 0.000 description 1
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- MTVSSSNUPMKSBD-UHFFFAOYSA-N 1-piperidin-4-yl-3-propan-2-ylbenzimidazol-2-one Chemical compound O=C1N(C(C)C)C2=CC=CC=C2N1C1CCNCC1 MTVSSSNUPMKSBD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-L 2,3-dihydroxybutanedioate Chemical compound [O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-L 0.000 description 1
- UUDLQDCYDSATCH-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;hydrate Chemical compound O.OC(=O)C(O)C(O)C(O)=O UUDLQDCYDSATCH-UHFFFAOYSA-N 0.000 description 1
- PXSBSBDNZRLRLK-UHFFFAOYSA-N 2-(2h-pyran-2-yloxy)-2h-pyran Chemical class O1C=CC=CC1OC1OC=CC=C1 PXSBSBDNZRLRLK-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- FRPNIZFUGKDSSS-UHFFFAOYSA-N 2-n-piperidin-4-ylbenzene-1,2-diamine Chemical class NC1=CC=CC=C1NC1CCNCC1 FRPNIZFUGKDSSS-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- JPDLWRGYOGEWID-UHFFFAOYSA-N 3-(2-nitroanilino)propan-1-ol Chemical compound OCCCNC1=CC=CC=C1[N+]([O-])=O JPDLWRGYOGEWID-UHFFFAOYSA-N 0.000 description 1
- GNCQCMAOLWLYOU-UHFFFAOYSA-N 3-(3-hydroxypropyl)-1h-benzimidazol-2-one Chemical compound C1=CC=C2NC(=O)N(CCCO)C2=C1 GNCQCMAOLWLYOU-UHFFFAOYSA-N 0.000 description 1
- BHXIYRGPJDFULT-UHFFFAOYSA-N 3-(3-hydroxypropyl)-1h-benzimidazol-2-one;hydrate Chemical compound O.C1=CC=C2NC(=O)N(CCCO)C2=C1 BHXIYRGPJDFULT-UHFFFAOYSA-N 0.000 description 1
- ZELXVUVWXATHED-UHFFFAOYSA-N 3-(3-hydroxypropyl)-1h-benzimidazol-2-one;methanesulfonic acid Chemical compound CS(O)(=O)=O.C1=CC=C2NC(=O)N(CCCO)C2=C1 ZELXVUVWXATHED-UHFFFAOYSA-N 0.000 description 1
- LVLKAZRCSJLJAT-UHFFFAOYSA-N 3-(3-hydroxypropyl)-6-methyl-1h-benzimidazol-2-one Chemical compound CC1=CC=C2N(CCCO)C(=O)NC2=C1 LVLKAZRCSJLJAT-UHFFFAOYSA-N 0.000 description 1
- OEEAQEQEGLABTM-UHFFFAOYSA-N 3-(3-hydroxypropyl)-6-methyl-1h-benzimidazol-2-one;methanesulfonic acid Chemical compound CS(O)(=O)=O.CC1=CC=C2N(CCCO)C(=O)NC2=C1 OEEAQEQEGLABTM-UHFFFAOYSA-N 0.000 description 1
- IDAYLLXJWYQWBQ-UHFFFAOYSA-N 3-[1-[3-(2-amino-5-chloroanilino)propyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound NC1=CC=C(Cl)C=C1NCCCN1CCC(N2C(NC3=CC=CC=C32)=O)CC1 IDAYLLXJWYQWBQ-UHFFFAOYSA-N 0.000 description 1
- XIAQZZALRRWUOW-UHFFFAOYSA-N 3-[1-[3-(2-aminoanilino)propyl]piperidin-4-yl]-6-chloro-1h-benzimidazol-2-one Chemical compound NC1=CC=CC=C1NCCCN1CCC(N2C(NC3=CC(Cl)=CC=C32)=O)CC1 XIAQZZALRRWUOW-UHFFFAOYSA-N 0.000 description 1
- WVBCLLDOAZEVRT-UHFFFAOYSA-N 3-[1-[3-(5-bromo-2-oxo-3h-benzimidazol-1-yl)propyl]piperidin-4-yl]-6-chloro-1h-benzimidazol-2-one Chemical compound C12=CC=C(Br)C=C2NC(=O)N1CCCN(CC1)CCC1N1C2=CC=C(Cl)C=C2NC1=O WVBCLLDOAZEVRT-UHFFFAOYSA-N 0.000 description 1
- WKHSXBWCASPRJC-UHFFFAOYSA-N 3-[1-[3-(benzimidazol-1-yl)propyl]piperidin-4-yl]-6-chloro-1h-benzimidazol-2-one Chemical compound C1=NC2=CC=CC=C2N1CCCN(CC1)CCC1N1C2=CC=C(Cl)C=C2NC1=O WKHSXBWCASPRJC-UHFFFAOYSA-N 0.000 description 1
- OHVBUPLSMXWMRR-UHFFFAOYSA-N 3-[1-[4-(benzimidazol-1-yl)butyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound C1=NC2=CC=CC=C2N1CCCCN(CC1)CCC1N1C2=CC=CC=C2NC1=O OHVBUPLSMXWMRR-UHFFFAOYSA-N 0.000 description 1
- OBHDXMCUKJATHF-UHFFFAOYSA-N 3-[3-[4-(2-oxo-3h-benzimidazol-1-yl)piperidin-1-yl]propyl]-1h-benzimidazol-2-one Chemical compound C12=CC=CC=C2NC(=O)N1C(CC1)CCN1CCCN1C2=CC=CC=C2NC1=O OBHDXMCUKJATHF-UHFFFAOYSA-N 0.000 description 1
- KCJXOVLCXFHEHU-UHFFFAOYSA-N 3-[3-[4-(2-sulfanylidene-3h-benzimidazol-1-yl)piperidin-1-yl]propyl]-1h-benzimidazol-2-one Chemical compound C12=CC=CC=C2NC(=S)N1C(CC1)CCN1CCCN1C2=CC=CC=C2NC1=O KCJXOVLCXFHEHU-UHFFFAOYSA-N 0.000 description 1
- XBJLLOGPGWLGRT-UHFFFAOYSA-N 3-[3-[4-(4-bromophenyl)-4-hydroxypiperidin-1-yl]propyl]-1h-benzimidazol-2-one Chemical compound C1CN(CCCN2C(NC3=CC=CC=C32)=O)CCC1(O)C1=CC=C(Br)C=C1 XBJLLOGPGWLGRT-UHFFFAOYSA-N 0.000 description 1
- PGVIMUPINRJXAB-UHFFFAOYSA-N 3-[3-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]propyl]-5,6-dimethyl-1h-benzimidazol-2-one;hydrochloride Chemical compound Cl.C1=2C=C(C)C(C)=CC=2NC(=O)N1CCCN(CC1)CCC1(O)C1=CC=C(Cl)C=C1 PGVIMUPINRJXAB-UHFFFAOYSA-N 0.000 description 1
- PDPDNBNZIBKTGI-UHFFFAOYSA-N 3-[3-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]propyl]-6-(trifluoromethyl)-1h-benzimidazol-2-one Chemical compound C1CN(CCCN2C(NC3=CC(=CC=C32)C(F)(F)F)=O)CCC1(O)C1=CC=C(Cl)C=C1 PDPDNBNZIBKTGI-UHFFFAOYSA-N 0.000 description 1
- OJBXYIMLPBGUJV-UHFFFAOYSA-N 3-[3-[4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl]propyl]-1h-benzimidazol-2-one Chemical compound C1CN(CCCN2C(NC3=CC=CC=C32)=O)CCC1(O)C1=CC=C(F)C=C1 OJBXYIMLPBGUJV-UHFFFAOYSA-N 0.000 description 1
- FRFOGIRTTGJKMT-UHFFFAOYSA-N 3-[3-[4-(5-chloro-2-methylsulfanylbenzimidazol-1-yl)piperidin-1-yl]propyl]-1h-benzimidazol-2-one Chemical compound C12=CC=CC=C2NC(=O)N1CCCN(CC1)CCC1N1C2=CC=C(Cl)C=C2N=C1SC FRFOGIRTTGJKMT-UHFFFAOYSA-N 0.000 description 1
- TUJUZSCBPRZQEH-UHFFFAOYSA-N 3-[3-[4-(5-chloro-2-oxo-3h-benzimidazol-1-yl)piperidin-1-yl]propyl]-5-methyl-1-prop-1-en-2-ylbenzimidazol-2-one Chemical compound C12=CC=C(Cl)C=C2NC(=O)N1C(CC1)CCN1CCCN1C2=CC(C)=CC=C2N(C(=C)C)C1=O TUJUZSCBPRZQEH-UHFFFAOYSA-N 0.000 description 1
- TZEBWFGKPBPSFL-UHFFFAOYSA-N 3-[3-[4-(5-chloro-2-oxo-3h-benzimidazol-1-yl)piperidin-1-yl]propyl]-6-fluoro-1h-benzimidazol-2-one;hydrate;hydrochloride Chemical compound O.Cl.C12=CC=C(Cl)C=C2NC(=O)N1C(CC1)CCN1CCCN1C2=CC=C(F)C=C2NC1=O TZEBWFGKPBPSFL-UHFFFAOYSA-N 0.000 description 1
- IMTPMOSXGNLWRK-UHFFFAOYSA-N 3-acetyl-1-[1-[3-(3-acetyl-2-oxobenzimidazol-1-yl)propyl]piperidin-4-yl]-5-chlorobenzimidazol-2-one Chemical compound C12=CC=C(Cl)C=C2N(C(C)=O)C(=O)N1C(CC1)CCN1CCCN1C2=CC=CC=C2N(C(=O)C)C1=O IMTPMOSXGNLWRK-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- IBGILWKRMWWQNS-UHFFFAOYSA-N 3-ethyl-1-(4-fluorophenyl)-8-[3-(2-oxo-3h-benzimidazol-1-yl)propyl]-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1CN(CCCN2C(NC3=CC=CC=C32)=O)CCC21C(=O)N(CC)CN2C1=CC=C(F)C=C1 IBGILWKRMWWQNS-UHFFFAOYSA-N 0.000 description 1
- BYNBAMHAURJNTR-UHFFFAOYSA-N 3-piperidin-4-yl-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1C1CCNCC1 BYNBAMHAURJNTR-UHFFFAOYSA-N 0.000 description 1
- LZAYOZUFUAMFLD-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-hydroxypiperidine Chemical compound C=1C=C(Cl)C=CC=1C1(O)CCNCC1 LZAYOZUFUAMFLD-UHFFFAOYSA-N 0.000 description 1
- QXWRXWPNHLIZBV-UHFFFAOYSA-N 4-(4-fluorophenyl)piperidin-4-ol Chemical compound C=1C=C(F)C=CC=1C1(O)CCNCC1 QXWRXWPNHLIZBV-UHFFFAOYSA-N 0.000 description 1
- AHFINSWGYAZBOZ-UHFFFAOYSA-N 4-chloro-2-(trifluoromethyl)benzaldehyde Chemical group FC(F)(F)C1=CC(Cl)=CC=C1C=O AHFINSWGYAZBOZ-UHFFFAOYSA-N 0.000 description 1
- PVBPSJYPNCNXNX-UHFFFAOYSA-N 4-chloro-3-(3-hydroxypropyl)-1h-benzimidazol-2-one;methanesulfonic acid Chemical compound CS(O)(=O)=O.C1=CC=C2NC(=O)N(CCCO)C2=C1Cl PVBPSJYPNCNXNX-UHFFFAOYSA-N 0.000 description 1
- LVQFHDAKZHGEAJ-UHFFFAOYSA-M 4-methylbenzenesulfonate Chemical compound [CH2]C1=CC=C(S([O-])(=O)=O)C=C1 LVQFHDAKZHGEAJ-UHFFFAOYSA-M 0.000 description 1
- MEXPSQZNVPJMOL-UHFFFAOYSA-N 5,6-dichloro-3-(3-hydroxypropyl)-1h-benzimidazol-2-one;methanesulfonic acid Chemical compound CS(O)(=O)=O.ClC1=C(Cl)C=C2NC(=O)N(CCCO)C2=C1 MEXPSQZNVPJMOL-UHFFFAOYSA-N 0.000 description 1
- PHQUFYZCQYQQMA-UHFFFAOYSA-N 5-chloro-1-[3-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]propyl]-3-prop-2-enylbenzimidazol-2-one Chemical compound C1CN(CCCN2C(N(CC=C)C3=CC(Cl)=CC=C32)=O)CCC1(O)C1=CC=C(Cl)C=C1 PHQUFYZCQYQQMA-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- SVABDCOHICFPFO-UHFFFAOYSA-N 5-chloro-3-[3-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]propyl]-1h-benzimidazol-2-one Chemical compound C1CN(CCCN2C(NC3=CC=C(Cl)C=C32)=O)CCC1(O)C1=CC=C(Cl)C=C1 SVABDCOHICFPFO-UHFFFAOYSA-N 0.000 description 1
- GZOOEXPEYKKUDL-UHFFFAOYSA-N 5-fluoro-3-(1-phenylprop-1-en-2-yl)-1h-benzimidazol-2-one Chemical compound C12=CC(F)=CC=C2NC(=O)N1C(C)=CC1=CC=CC=C1 GZOOEXPEYKKUDL-UHFFFAOYSA-N 0.000 description 1
- UWHKXAZJRDKPSL-UHFFFAOYSA-N 6-bromo-3-[1-[3-(2-oxo-3h-benzimidazol-1-yl)propyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound C12=CC=CC=C2NC(=O)N1CCCN(CC1)CCC1N1C2=CC=C(Br)C=C2NC1=O UWHKXAZJRDKPSL-UHFFFAOYSA-N 0.000 description 1
- CCRZLRHXIXAQSU-UHFFFAOYSA-N 6-chloro-3-[1-[2-methyl-3-(2-oxo-3h-benzimidazol-1-yl)propyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound C12=CC=CC=C2NC(=O)N1CC(C)CN1CCC(N2C(NC3=CC(Cl)=CC=C32)=O)CC1 CCRZLRHXIXAQSU-UHFFFAOYSA-N 0.000 description 1
- QNSJBZUANODBFB-UHFFFAOYSA-N 6-chloro-3-[1-[3-(2-oxo-3h-benzimidazol-1-yl)propyl]piperidin-4-yl]-1h-benzimidazol-2-one;hydrate;hydrochloride Chemical compound O.Cl.C12=CC=CC=C2NC(=O)N1CCCN(CC1)CCC1N1C2=CC=C(Cl)C=C2NC1=O QNSJBZUANODBFB-UHFFFAOYSA-N 0.000 description 1
- UJEOLXBWZMTIAT-UHFFFAOYSA-N 6-chloro-3-[3-[4-(2-oxo-3h-benzimidazol-1-yl)piperidin-1-yl]propyl]-1h-benzimidazol-2-one Chemical compound C12=CC=CC=C2NC(=O)N1C(CC1)CCN1CCCN1C2=CC=C(Cl)C=C2NC1=O UJEOLXBWZMTIAT-UHFFFAOYSA-N 0.000 description 1
- OGJKHRLTKUVUQC-UHFFFAOYSA-N 6-chloro-3-[3-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]propyl]-1h-benzimidazol-2-one Chemical compound C1CN(CCCN2C(NC3=CC(Cl)=CC=C32)=O)CCC1(O)C1=CC=C(Cl)C=C1 OGJKHRLTKUVUQC-UHFFFAOYSA-N 0.000 description 1
- ISNGZEAJZIHYRA-UHFFFAOYSA-N 6-chloro-3-[3-[4-(5-chloro-2-oxo-3h-benzimidazol-1-yl)piperidin-1-yl]-2-methylpropyl]-1h-benzimidazol-2-one Chemical compound C12=CC=C(Cl)C=C2NC(=O)N1CC(C)CN1CCC(N2C(NC3=CC(Cl)=CC=C32)=O)CC1 ISNGZEAJZIHYRA-UHFFFAOYSA-N 0.000 description 1
- FUHOBHCCYRVHJI-UHFFFAOYSA-N 6-chloro-3-[3-[4-[4-chloro-3-(trifluoromethyl)phenyl]-4-hydroxypiperidin-1-yl]propyl]-1h-benzimidazol-2-one Chemical compound C1CN(CCCN2C(NC3=CC(Cl)=CC=C32)=O)CCC1(O)C1=CC=C(Cl)C(C(F)(F)F)=C1 FUHOBHCCYRVHJI-UHFFFAOYSA-N 0.000 description 1
- UZJVMEKPIPHRFG-UHFFFAOYSA-N 8-[3-(2-oxo-3h-benzimidazol-1-yl)propyl]-1-[3-(trifluoromethyl)phenyl]-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound FC(F)(F)C1=CC=CC(N2C3(CCN(CCCN4C(NC5=CC=CC=C54)=O)CC3)C(=O)NC2)=C1 UZJVMEKPIPHRFG-UHFFFAOYSA-N 0.000 description 1
- IBNBQEMKTOLMBT-UHFFFAOYSA-N 8-[3-(2-oxo-3h-benzimidazol-1-yl)propyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1CN(CCCN2C(NC3=CC=CC=C32)=O)CCC11C(=O)NCN1C1=CC=CC=C1 IBNBQEMKTOLMBT-UHFFFAOYSA-N 0.000 description 1
- NOKYGSLUODTQCA-UHFFFAOYSA-N 8-[3-(3-methyl-2-oxobenzimidazol-1-yl)propyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound O=C1N(C)C2=CC=CC=C2N1CCCN(CC1)CCC1(C(NC1)=O)N1C1=CC=CC=C1 NOKYGSLUODTQCA-UHFFFAOYSA-N 0.000 description 1
- WIXDELPHHDYPLA-UHFFFAOYSA-N 8-[3-(5,6-dimethyl-2-oxo-3h-benzimidazol-1-yl)propyl]-1-(4-fluorophenyl)-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1=2C=C(C)C(C)=CC=2NC(=O)N1CCCN(CC1)CCC1(C(NC1)=O)N1C1=CC=C(F)C=C1 WIXDELPHHDYPLA-UHFFFAOYSA-N 0.000 description 1
- ONCJHIXIJOBEIJ-UHFFFAOYSA-N 8-[3-(5-chloro-2-oxo-3h-benzimidazol-1-yl)propyl]-1-(4-fluorophenyl)-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1=CC(F)=CC=C1N1C2(CCN(CCCN3C(NC4=CC(Cl)=CC=C43)=O)CC2)C(=O)NC1 ONCJHIXIJOBEIJ-UHFFFAOYSA-N 0.000 description 1
- YSUVBIKKWGFXOB-UHFFFAOYSA-N 8-[3-(5-methyl-2-oxo-3h-benzimidazol-1-yl)propyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound O=C1NC2=CC(C)=CC=C2N1CCCN(CC1)CCC1(C(NC1)=O)N1C1=CC=CC=C1 YSUVBIKKWGFXOB-UHFFFAOYSA-N 0.000 description 1
- YKIFAYYTVKMBDS-UHFFFAOYSA-N 8-[3-(6-chloro-2-oxo-3h-benzimidazol-1-yl)propyl]-1-(4-fluorophenyl)-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1=CC(F)=CC=C1N1C2(CCN(CCCN3C(NC4=CC=C(Cl)C=C43)=O)CC2)C(=O)NC1 YKIFAYYTVKMBDS-UHFFFAOYSA-N 0.000 description 1
- GNLXALIJPRFFJB-UHFFFAOYSA-N 8-[3-(6-chloro-2-oxo-3h-benzimidazol-1-yl)propyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C12=CC(Cl)=CC=C2NC(=O)N1CCCN(CC1)CCC1(C(NC1)=O)N1C1=CC=CC=C1 GNLXALIJPRFFJB-UHFFFAOYSA-N 0.000 description 1
- ZYRMDNLJRIBWNC-UHFFFAOYSA-N 8-[3-(benzimidazol-1-yl)propyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1CN(CCCN2C3=CC=CC=C3N=C2)CCC11C(=O)NCN1C1=CC=CC=C1 ZYRMDNLJRIBWNC-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 102000001324 CD59 Antigens Human genes 0.000 description 1
- 108010055167 CD59 Antigens Proteins 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229920003091 Methocel™ Polymers 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 240000007651 Rubus glaucus Species 0.000 description 1
- 244000235659 Rubus idaeus Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 230000002006 anti-spasmogenic effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000008641 benzimidazolones Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000000332 continued effect Effects 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- MKJDUHZPLQYUCB-UHFFFAOYSA-N decan-4-one Chemical compound CCCCCCC(=O)CCC MKJDUHZPLQYUCB-UHFFFAOYSA-N 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- PWRUKIPYVGHRFL-UHFFFAOYSA-N ethyl 3-oxo-2-phenylbutanoate Chemical compound CCOC(=O)C(C(C)=O)C1=CC=CC=C1 PWRUKIPYVGHRFL-UHFFFAOYSA-N 0.000 description 1
- GMDPPHXPURQLKC-UHFFFAOYSA-N ethyl 4-(4-chloro-2-nitroanilino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NC1=CC=C(Cl)C=C1[N+]([O-])=O GMDPPHXPURQLKC-UHFFFAOYSA-N 0.000 description 1
- 229940058172 ethylbenzene Drugs 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000004694 iodide salts Chemical group 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910001511 metal iodide Inorganic materials 0.000 description 1
- 229940057952 methanol Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 229940098462 oral drops Drugs 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- QRKVRHZNLKTPGF-UHFFFAOYSA-N phosphorus pentabromide Chemical compound BrP(Br)(Br)(Br)Br QRKVRHZNLKTPGF-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- RMIGTEGRHJUHHM-UHFFFAOYSA-N propan-1-ol;hydrochloride Chemical compound Cl.CCCO RMIGTEGRHJUHHM-UHFFFAOYSA-N 0.000 description 1
- DKORSYDQYFVQNS-UHFFFAOYSA-N propyl methanesulfonate Chemical compound CCCOS(C)(=O)=O DKORSYDQYFVQNS-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 101150115956 slc25a26 gene Proteins 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent 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
- 238000007910 systemic administration Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/26—Oxygen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Otolaryngology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hospice & Palliative Care (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59779375A | 1975-07-21 | 1975-07-21 | |
| US05/687,139 US4066772A (en) | 1975-07-21 | 1976-05-17 | 1,3-Dihydro-1-[3-(1-piperidinyl)propyl]-2H-benzimidazol-2-ones and related compounds |
| US687,139 | 1976-05-17 | ||
| KR7601697A KR810000334B1 (ko) | 1975-07-21 | 1976-07-12 | 1-(벤즈 아조릴알킬) 피페리딘 유도체의 제조방법 |
| US597,793 | 1984-04-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1085852A true CA1085852A (en) | 1980-09-16 |
Family
ID=27348142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA256,450A Expired CA1085852A (en) | 1975-07-21 | 1976-07-07 | 1,3-dihydro-1- 3-(1-piperidinyl)propyl -2h- benzimidazol-2-ones and related compounds |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS5217475A (is") |
| AT (1) | AT364358B (is") |
| AU (1) | AU511027B2 (is") |
| BG (1) | BG26526A3 (is") |
| CA (1) | CA1085852A (is") |
| CH (1) | CH623820A5 (is") |
| CS (1) | CS202550B2 (is") |
| DE (1) | DE2632870A1 (is") |
| DK (1) | DK154950C (is") |
| ES (3) | ES449740A1 (is") |
| FI (1) | FI62667C (is") |
| GB (1) | GB1542514A (is") |
| HK (1) | HK14180A (is") |
| IE (1) | IE43496B1 (is") |
| IT (1) | IT1062614B (is") |
| KE (1) | KE3215A (is") |
| LU (1) | LU75354A1 (is") |
| MY (1) | MY8100017A (is") |
| NL (1) | NL187442C (is") |
| NZ (1) | NZ181256A (is") |
| PH (1) | PH13710A (is") |
| PT (1) | PT65387B (is") |
| RO (1) | RO70566A (is") |
| SE (2) | SE426490B (is") |
| YU (1) | YU39969B (is") |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8846929B2 (en) | 2007-08-31 | 2014-09-30 | Purdue Pharma L.P. | Substituted-quinoxaline-type piperidine compounds and the uses thereof |
| US9090618B2 (en) | 2012-12-27 | 2015-07-28 | Purdue Pharma L.P. | Substituted benzimidazole-type piperidine compounds and uses thereof |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4501749A (en) * | 1983-10-31 | 1985-02-26 | Merck & Co., Inc. | Peripherally selective dopamine antagonists in the treatment of ocular hypertension |
| JPS6248684A (ja) * | 1985-08-26 | 1987-03-03 | Sumitomo Chem Co Ltd | 新規なヨ−ドブチロフエノン誘導体およびその製造法 |
| JPS62251313A (ja) * | 1986-04-25 | 1987-11-02 | 信越ポリマー株式会社 | 結束装置 |
| US6355659B1 (en) | 1994-07-29 | 2002-03-12 | Laboratorios Del Dr. Esteve, S.A. | 4-(4-Chlorophenyl)-1236-tetrahydro-1(1H-124-triazol-1-yl)butty)pyrideine and salts thereof; pharmaceutical compositions and method of treating psychoses utilizing same |
| FR2723091B1 (fr) * | 1994-07-29 | 1996-11-08 | Esteve Labor Dr | Tetrahydropyridine-(6,4-hydroxypiperidine) alkylazoles |
| RU2192848C1 (ru) * | 2001-10-30 | 2002-11-20 | Закрытое акционерное общество "ВЕРОФАРМ" | Противорвотное средство |
| PA8603801A1 (es) | 2003-05-27 | 2004-12-16 | Janssen Pharmaceutica Nv | Derivados de la quinazolina |
| RU2268047C2 (ru) * | 2003-12-15 | 2006-01-20 | Закрытое акционерное общество "Фармацевтическое предприятие "Оболенское" | Лекарственная форма, обладающая противорвотным действием, и способ ее изготовления |
| DE602004012891T2 (de) | 2003-12-18 | 2009-04-09 | Janssen Pharmaceutica N.V. | Pyrido- und pyrimidopyrimidinderivate als anti-proliferative mittel |
| NI200700147A (es) | 2004-12-08 | 2019-05-10 | Janssen Pharmaceutica Nv | Derivados de quinazolina inhibidores de cinasas dirigidos a multip |
| MX2009000456A (es) | 2006-07-13 | 2009-01-27 | Janssen Pharmaceutica Nv | Derivados de quinazolina mtki. |
| EP1997805A1 (en) * | 2007-06-01 | 2008-12-03 | Commissariat à l'Energie Atomique | Compounds with antiparasitic activity, applications thereof to the treatment of infectious diseases caused by apicomplexans |
| JP5536647B2 (ja) | 2007-07-27 | 2014-07-02 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | ピロロピリミジン |
| BR112018016032B1 (pt) * | 2016-02-04 | 2024-03-05 | Cindome Pharma, Inc | Compostos, composição farmacêutica e uso dos mesmos para melhorar um distúrbio |
| US11364226B2 (en) | 2017-06-30 | 2022-06-21 | Cinrx Pharma, Llc | Deuterated domperidone compositions, methods, and preparation |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE633495A (is") * | 1962-06-13 | |||
| BE633914A (is") * | 1962-06-22 | |||
| US3629267A (en) * | 1968-10-28 | 1971-12-21 | Smith Kline French Lab | Benzoheterocyclicalkyl derivatives of 4-(2-keto -1-benzimidazolinyl)-piperidine 4-(2-keto - 1 - benzimidazolinyl) -1 2 3 6 tetrahydropyridine 1 - phenyl - 1 3 8-triazaspiro(4 5)decan - 4 - one and 2 4 9-triazaspiro(5 5)undecan-1 3 5-trione |
| AU4698672A (en) * | 1972-09-22 | 1972-11-09 | Ciba-Geigy Ag | Azacycloaliphatic compounds, process for their manufacture and compositions containing them |
| FR2218100A1 (en) * | 1973-02-20 | 1974-09-13 | Janssen Pharmaceutica Nv | Neuroleptic tricyclic derivs. - of benzimidazolinones and triazaspiro-4,5-decan-4-ones |
| US3989707A (en) * | 1974-06-21 | 1976-11-02 | Janssen Pharmaceutica N.V. | Benzimidazolinone derivatives |
-
1976
- 1976-06-23 NZ NZ181256A patent/NZ181256A/xx unknown
- 1976-06-30 GB GB7627242A patent/GB1542514A/en not_active Expired
- 1976-07-07 RO RO7686860A patent/RO70566A/ro unknown
- 1976-07-07 CA CA256,450A patent/CA1085852A/en not_active Expired
- 1976-07-08 PH PH18663A patent/PH13710A/en unknown
- 1976-07-09 LU LU75354A patent/LU75354A1/xx unknown
- 1976-07-09 ES ES449740A patent/ES449740A1/es not_active Expired
- 1976-07-16 CS CS764688A patent/CS202550B2/cs unknown
- 1976-07-16 AU AU15964/76A patent/AU511027B2/en not_active Expired
- 1976-07-19 JP JP51085216A patent/JPS5217475A/ja active Granted
- 1976-07-19 IT IT50499/76A patent/IT1062614B/it active
- 1976-07-20 IE IE1602/76A patent/IE43496B1/en not_active IP Right Cessation
- 1976-07-20 BG BG033791A patent/BG26526A3/xx unknown
- 1976-07-20 CH CH929176A patent/CH623820A5/de not_active IP Right Cessation
- 1976-07-20 SE SE7608265A patent/SE426490B/xx not_active IP Right Cessation
- 1976-07-20 AT AT0534776A patent/AT364358B/de not_active IP Right Cessation
- 1976-07-20 NL NLAANVRAGE7608023,A patent/NL187442C/xx not_active IP Right Cessation
- 1976-07-20 DK DK327576A patent/DK154950C/da not_active IP Right Cessation
- 1976-07-20 FI FI762086A patent/FI62667C/fi not_active IP Right Cessation
- 1976-07-20 PT PT65387A patent/PT65387B/pt unknown
- 1976-07-21 DE DE19762632870 patent/DE2632870A1/de active Granted
- 1976-07-21 YU YU1794/76A patent/YU39969B/xx unknown
-
1977
- 1977-08-16 ES ES461630A patent/ES461630A1/es not_active Expired
- 1977-08-16 ES ES461631A patent/ES461631A1/es not_active Expired
-
1980
- 1980-03-20 HK HK141/80A patent/HK14180A/xx unknown
- 1980-12-11 SE SE8008713A patent/SE435621B/sv not_active IP Right Cessation
-
1981
- 1981-12-30 MY MY17/81A patent/MY8100017A/xx unknown
-
1982
- 1982-05-21 KE KE3215A patent/KE3215A/xx unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8846929B2 (en) | 2007-08-31 | 2014-09-30 | Purdue Pharma L.P. | Substituted-quinoxaline-type piperidine compounds and the uses thereof |
| US9278967B2 (en) | 2007-08-31 | 2016-03-08 | Purdue Pharma L.P. | Substituted-quinoxaline-type piperidine compounds and the uses thereof |
| US9527840B2 (en) | 2007-08-31 | 2016-12-27 | Purdue Pharma L.P. | Substituted-quinoxaline-type piperidine compounds and the uses thereof |
| US9090618B2 (en) | 2012-12-27 | 2015-07-28 | Purdue Pharma L.P. | Substituted benzimidazole-type piperidine compounds and uses thereof |
| US9598411B2 (en) | 2012-12-27 | 2017-03-21 | Purdue Pharma L.P. | Substituted benzimidazole-type piperidine compounds and uses thereof |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1085852A (en) | 1,3-dihydro-1- 3-(1-piperidinyl)propyl -2h- benzimidazol-2-ones and related compounds | |
| US4066772A (en) | 1,3-Dihydro-1-[3-(1-piperidinyl)propyl]-2H-benzimidazol-2-ones and related compounds | |
| US4200641A (en) | 1-[(Heterocyclyl)-alkyl]-4-diarylmethoxy piperidine derivatives | |
| EP0005318B1 (en) | N-heterocyclyl-4-piperidinamines, methods for their preparation, pharmaceutical compositions comprising them, intermediates therefor, and method for the preparation of the intermediates | |
| US4219559A (en) | N-Heterocyclyl-4-piperidinamines | |
| US4031226A (en) | N-[(1-piperidinyl)alkyl]arylcarboxamide derivatives | |
| IE53400B1 (en) | Novel bicyclic pyrimidin-5-one derivatives | |
| CA1085853A (en) | 1-benzazolylalkyl-4-substituted-piperidines | |
| US4250176A (en) | Piperazine derivatives | |
| DK163239B (da) | N-(bicykliske heterocyklyl)-4-piperidinaminer, en fremgangsmaade til fremstilling deraf samt antiallergiske praeparater indeholdende dem | |
| US4126687A (en) | Antiemetic, 1-(benzimidazolyl-alkyl)-piperidine derivatives | |
| HU221298B1 (en) | Substituted thiazolyl and pyridyl derivatives and pharmaceutical compositions comprising same and process for producing them | |
| EP0037713B1 (en) | Novel 1,3-dihydro-1-((1-piperidinyl)alkyl)-2h-benzimidazol-2-one derivatives | |
| US4377578A (en) | Piperazine derivatives | |
| US4175129A (en) | Antiemetic 1-(benzoxazolylalkyl)-piperidine derivatives | |
| US5378714A (en) | Antipsychotic piperidine derivatives | |
| KR800000491B1 (ko) | 1-벤즈아조릴알킬-4-치환된 피페리딘의 제조방법 | |
| PL118633B1 (en) | Method of manufacture of novel derivatives of 1-/benzazolyl-alkyl/-piperidineil/-piperidina | |
| FI65249B (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara 1-enyl-8-bensimidazol-1-ylpropyl-1,3,8-triazaspiro(4,5)-dek an4-onderivat | |
| PL102727B1 (pl) | Sposob wytwarzania nowych n-/(1-piperydynylo)-alkilo/arylokarbonamidow |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |