JPS6231707B2 - - Google Patents
Info
- Publication number
- JPS6231707B2 JPS6231707B2 JP52035560A JP3556077A JPS6231707B2 JP S6231707 B2 JPS6231707 B2 JP S6231707B2 JP 52035560 A JP52035560 A JP 52035560A JP 3556077 A JP3556077 A JP 3556077A JP S6231707 B2 JPS6231707 B2 JP S6231707B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- parts
- formula
- lower alkyl
- dihydro
- 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 claims description 60
- 239000000203 mixture Substances 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 239000002253 acid Substances 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims description 11
- 230000001387 anti-histamine Effects 0.000 claims description 11
- 239000000739 antihistaminic agent Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 230000002804 anti-anaphylactic effect Effects 0.000 claims description 9
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 7
- BAINIUMDFURPJM-UHFFFAOYSA-N oxatomide Chemical compound O=C1NC2=CC=CC=C2N1CCCN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 BAINIUMDFURPJM-UHFFFAOYSA-N 0.000 claims description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- HHRFWSALGNYPHA-UHFFFAOYSA-N [N].C1CNCCN1 Chemical group [N].C1CNCCN1 HHRFWSALGNYPHA-UHFFFAOYSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- 150000002829 nitrogen Chemical class 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 150000008641 benzimidazolones Chemical group 0.000 claims 1
- 239000012876 carrier material Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 238000002844 melting Methods 0.000 description 39
- 230000008018 melting Effects 0.000 description 39
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 239000000047 product Substances 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 26
- -1 cyclic hydrocarbon radical Chemical group 0.000 description 24
- 238000000034 method Methods 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 150000002148 esters Chemical class 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 20
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 229960001701 chloroform Drugs 0.000 description 15
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 14
- 239000003480 eluent Substances 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 12
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 12
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 239000013067 intermediate product Substances 0.000 description 12
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
- 125000006239 protecting group Chemical group 0.000 description 12
- 239000000284 extract Substances 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 229960001340 histamine Drugs 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- NWVNXDKZIQLBNM-UHFFFAOYSA-N diphenylmethylpiperazine Chemical compound C1CNCCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 NWVNXDKZIQLBNM-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 150000004885 piperazines Chemical class 0.000 description 5
- 239000012258 stirred mixture Substances 0.000 description 5
- TTXIFFYPVGWLSE-UHFFFAOYSA-N 1-[bis(4-fluorophenyl)methyl]piperazine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)N1CCNCC1 TTXIFFYPVGWLSE-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000003937 drug carrier Substances 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 150000003053 piperidines Chemical class 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- 108010058846 Ovalbumin Proteins 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 238000007429 general method Methods 0.000 description 3
- 210000000548 hind-foot Anatomy 0.000 description 3
- 229940092253 ovalbumin Drugs 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- WDHJXSIVNBJRNZ-UHFFFAOYSA-N (2,4-dichlorophenyl)-(4-fluorophenyl)methanol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)C1=CC=C(F)C=C1 WDHJXSIVNBJRNZ-UHFFFAOYSA-N 0.000 description 2
- CRLDYDFRKDTPNY-UHFFFAOYSA-N 1-(4-chlorobutyl)benzimidazole Chemical compound C1=CC=C2N(CCCCCl)C=NC2=C1 CRLDYDFRKDTPNY-UHFFFAOYSA-N 0.000 description 2
- XXJYADWNXZSNSB-UHFFFAOYSA-N 1-[3-(4-benzylpiperazin-1-yl)propyl]-3-prop-1-en-2-ylbenzimidazol-2-one Chemical compound O=C1N(C(=C)C)C2=CC=CC=C2N1CCCN(CC1)CCN1CC1=CC=CC=C1 XXJYADWNXZSNSB-UHFFFAOYSA-N 0.000 description 2
- ANNPMLHVZLXDBW-UHFFFAOYSA-N 3-(3-piperazin-1-ylpropyl)-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1CCCN1CCNCC1 ANNPMLHVZLXDBW-UHFFFAOYSA-N 0.000 description 2
- YOMHAEQWLKOJKR-UHFFFAOYSA-N 3-[3-[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl]propyl]-1h-benzimidazol-2-one Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)N1CCN(CCCN2C(NC3=CC=CC=C32)=O)CC1 YOMHAEQWLKOJKR-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- HXROHDYGZFFVMO-UHFFFAOYSA-N 4-benzhydryloxypiperidine;hydrochloride Chemical compound [Cl-].C1C[NH2+]CCC1OC(C=1C=CC=CC=1)C1=CC=CC=C1 HXROHDYGZFFVMO-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 230000006181 N-acylation Effects 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid Chemical compound OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- LGFDTDYQENHPEM-UHFFFAOYSA-N ethyl 2-[3-[3-(4-benzhydrylpiperazin-1-yl)propyl]-2-oxobenzimidazol-1-yl]acetate Chemical compound O=C1N(CC(=O)OCC)C2=CC=CC=C2N1CCCN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 LGFDTDYQENHPEM-UHFFFAOYSA-N 0.000 description 2
- NXNZOUDBPNGRMT-UHFFFAOYSA-N ethyl 4-[bis(4-fluorophenyl)methoxy]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1OC(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 NXNZOUDBPNGRMT-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 210000002683 foot Anatomy 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 2
- BQTDQOMYIBXMCG-UHFFFAOYSA-N n-[3-(4-benzhydrylpiperazin-1-yl)propyl]-2-nitroaniline;hydrochloride Chemical compound Cl.[O-][N+](=O)C1=CC=CC=C1NCCCN1CCN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 BQTDQOMYIBXMCG-UHFFFAOYSA-N 0.000 description 2
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000012071 phase Substances 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- UVAKGOJIHCGXID-UHFFFAOYSA-N (2,4-dichlorophenyl)-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(Cl)C=C1Cl UVAKGOJIHCGXID-UHFFFAOYSA-N 0.000 description 1
- ZTEUMIJDSVRAPD-UHFFFAOYSA-N (4-chlorophenyl)-(2-fluorophenyl)methanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=C(Cl)C=C1 ZTEUMIJDSVRAPD-UHFFFAOYSA-N 0.000 description 1
- HUQCTWLEMXTXSV-UHFFFAOYSA-N (4-fluorophenyl)-pyridin-3-ylmethanol;hydrochloride Chemical compound Cl.C=1C=CN=CC=1C(O)C1=CC=C(F)C=C1 HUQCTWLEMXTXSV-UHFFFAOYSA-N 0.000 description 1
- JIGAKCVAQRKZOU-UHFFFAOYSA-N (4-methoxyphenyl)-[3-(trifluoromethyl)phenyl]methanol Chemical compound C1=CC(OC)=CC=C1C(O)C1=CC=CC(C(F)(F)F)=C1 JIGAKCVAQRKZOU-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-ZETCQYMHSA-N (S)-mandelic acid Chemical compound OC(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-N 0.000 description 1
- IBRBMZRLVYKVRF-UHFFFAOYSA-N 1,2,4-trichloro-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=C(Cl)C=C1Cl IBRBMZRLVYKVRF-UHFFFAOYSA-N 0.000 description 1
- CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 description 1
- KDIBZWMKHBFSGC-UHFFFAOYSA-N 1,4,7,10,13,16-hexaoxacyclooctadeca-8,17-diene Chemical compound C1COC=COCCOCCOC=COCCO1 KDIBZWMKHBFSGC-UHFFFAOYSA-N 0.000 description 1
- OMIVCRYZSXDGAB-UHFFFAOYSA-N 1,4-butanediyl Chemical group [CH2]CC[CH2] OMIVCRYZSXDGAB-UHFFFAOYSA-N 0.000 description 1
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-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
- ZXEJMYXQANEOMP-UHFFFAOYSA-N 1-(3-chloropropyl)benzimidazole Chemical compound C1=CC=C2N(CCCCl)C=NC2=C1 ZXEJMYXQANEOMP-UHFFFAOYSA-N 0.000 description 1
- IRHBRUZHVQKGMQ-UHFFFAOYSA-N 1-(5-chloropentyl)-3-prop-1-en-2-ylbenzimidazol-2-one Chemical compound C1=CC=C2N(CCCCCCl)C(=O)N(C(=C)C)C2=C1 IRHBRUZHVQKGMQ-UHFFFAOYSA-N 0.000 description 1
- JIDAQAUNMWTROG-UHFFFAOYSA-N 1-[(2-chlorophenyl)-(3-chlorophenyl)methyl]piperazine Chemical compound ClC1=CC=CC(C(N2CCNCC2)C=2C(=CC=CC=2)Cl)=C1 JIDAQAUNMWTROG-UHFFFAOYSA-N 0.000 description 1
- KKMSCNTZDCYNSC-UHFFFAOYSA-N 1-[(4-fluorophenyl)-phenylmethyl]piperazine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 KKMSCNTZDCYNSC-UHFFFAOYSA-N 0.000 description 1
- NVWKWNDZVYDGFJ-UHFFFAOYSA-N 1-[(4-nitrophenyl)-phenylmethyl]piperazine;dihydrochloride Chemical compound Cl.Cl.C1=CC([N+](=O)[O-])=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 NVWKWNDZVYDGFJ-UHFFFAOYSA-N 0.000 description 1
- YURPKXQEKWZAER-UHFFFAOYSA-N 1-[3-(4-benzhydrylpiperazin-1-yl)propyl]-3-(hydroxymethyl)benzimidazol-2-one Chemical compound O=C1N(CO)C2=CC=CC=C2N1CCCN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 YURPKXQEKWZAER-UHFFFAOYSA-N 0.000 description 1
- NYZOMXCRNXVXAU-UHFFFAOYSA-N 1-[4-[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl]butyl]benzimidazole Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)N1CCN(CCCCN2C3=CC=CC=C3N=C2)CC1 NYZOMXCRNXVXAU-UHFFFAOYSA-N 0.000 description 1
- HXDAZUSPEXGQSS-UHFFFAOYSA-N 1-[bromo-(4-fluorophenyl)methyl]-4-fluorobenzene Chemical compound C1=CC(F)=CC=C1C(Br)C1=CC=C(F)C=C1 HXDAZUSPEXGQSS-UHFFFAOYSA-N 0.000 description 1
- WDCJXNOVLUBNOQ-UHFFFAOYSA-N 1-[chloro(phenyl)methyl]-2,3-dimethylbenzene Chemical compound CC1=CC=CC(C(Cl)C=2C=CC=CC=2)=C1C WDCJXNOVLUBNOQ-UHFFFAOYSA-N 0.000 description 1
- CXGGLEFWQVJQLN-UHFFFAOYSA-N 1-[chloro(phenyl)methyl]-2,4-dimethylbenzene Chemical compound CC1=CC(C)=CC=C1C(Cl)C1=CC=CC=C1 CXGGLEFWQVJQLN-UHFFFAOYSA-N 0.000 description 1
- JZDFGWQHADEECT-UHFFFAOYSA-N 1-[chloro(phenyl)methyl]-2-fluorobenzene Chemical compound FC1=CC=CC=C1C(Cl)C1=CC=CC=C1 JZDFGWQHADEECT-UHFFFAOYSA-N 0.000 description 1
- KJNTUYDTJPRSFA-UHFFFAOYSA-N 1-[chloro-(4-fluorophenyl)methyl]-4-methylbenzene Chemical compound C1=CC(C)=CC=C1C(Cl)C1=CC=C(F)C=C1 KJNTUYDTJPRSFA-UHFFFAOYSA-N 0.000 description 1
- ZTPNAUXCSMDJTR-UHFFFAOYSA-N 1-acetyl-3-[3-(4-benzhydrylpiperazin-1-yl)propyl]benzimidazol-2-one Chemical compound O=C1N(C(=O)C)C2=CC=CC=C2N1CCCN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 ZTPNAUXCSMDJTR-UHFFFAOYSA-N 0.000 description 1
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-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
- 125000006028 1-methyl-2-butenyl group Chemical group 0.000 description 1
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- BZCOSCNPHJNQBP-UHFFFAOYSA-N 2,3-dihydroxybut-2-enedioic acid Chemical compound OC(=O)C(O)=C(O)C(O)=O BZCOSCNPHJNQBP-UHFFFAOYSA-N 0.000 description 1
- VPNLMIQYUVBSGZ-UHFFFAOYSA-N 2,4-dichloro-1-[chloro-(4-fluorophenyl)methyl]benzene Chemical compound C1=CC(F)=CC=C1C(Cl)C1=CC=C(Cl)C=C1Cl VPNLMIQYUVBSGZ-UHFFFAOYSA-N 0.000 description 1
- CEOCVKWBUWKBKA-UHFFFAOYSA-N 2,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1Cl CEOCVKWBUWKBKA-UHFFFAOYSA-N 0.000 description 1
- NJZCRXQWPNNJNB-UHFFFAOYSA-N 2-[2-nitro-4-(trifluoromethyl)anilino]ethanol Chemical compound OCCNC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O NJZCRXQWPNNJNB-UHFFFAOYSA-N 0.000 description 1
- TUNIGDULNXJQFD-UHFFFAOYSA-N 2-[3-[3-(4-benzhydrylpiperazin-1-yl)propyl]-2-oxobenzimidazol-1-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C2=CC=CC=C2N1CCCN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 TUNIGDULNXJQFD-UHFFFAOYSA-N 0.000 description 1
- WKZRHEQZMOGOFQ-UHFFFAOYSA-N 2-[chloro(phenyl)methyl]-1,4-dimethylbenzene Chemical compound CC1=CC=C(C)C(C(Cl)C=2C=CC=CC=2)=C1 WKZRHEQZMOGOFQ-UHFFFAOYSA-N 0.000 description 1
- XLAQODLRPYMKBX-UHFFFAOYSA-N 2-[chloro(phenyl)methyl]pyridine;hydrochloride Chemical compound [Cl-].C=1C=CC=[NH+]C=1C(Cl)C1=CC=CC=C1 XLAQODLRPYMKBX-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- LODHFNUFVRVKTH-ZHACJKMWSA-N 2-hydroxy-n'-[(e)-3-phenylprop-2-enoyl]benzohydrazide Chemical compound OC1=CC=CC=C1C(=O)NNC(=O)\C=C\C1=CC=CC=C1 LODHFNUFVRVKTH-ZHACJKMWSA-N 0.000 description 1
- UWYVPFMHMJIBHE-UHFFFAOYSA-N 2-hydroxybut-2-enedioic acid Chemical compound OC(=O)C=C(O)C(O)=O UWYVPFMHMJIBHE-UHFFFAOYSA-N 0.000 description 1
- LLHAOVVBCWTUOF-UHFFFAOYSA-N 2-n-[3-(4-benzhydrylpiperazin-1-yl)propyl]benzene-1,2-diamine;hydrochloride Chemical compound Cl.NC1=CC=CC=C1NCCCN1CCN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 LLHAOVVBCWTUOF-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
- KCCGDFBIWOGUJZ-UHFFFAOYSA-N 3-(2-piperazin-1-ylethyl)-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1CCN1CCNCC1 KCCGDFBIWOGUJZ-UHFFFAOYSA-N 0.000 description 1
- 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 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
- UDXBXNMUCAZWPI-UHFFFAOYSA-N 3-(4,5-dichloro-2-nitroanilino)propan-1-ol Chemical compound OCCCNC1=CC(Cl)=C(Cl)C=C1[N+]([O-])=O UDXBXNMUCAZWPI-UHFFFAOYSA-N 0.000 description 1
- HLJJJPMNIFNKCI-UHFFFAOYSA-N 3-(4-chlorobutyl)-1h-benzimidazol-2-one Chemical compound C1=CC=C2NC(=O)N(CCCCCl)C2=C1 HLJJJPMNIFNKCI-UHFFFAOYSA-N 0.000 description 1
- IPBSBUQDPNMEBC-UHFFFAOYSA-N 3-[2-(4-benzhydrylpiperazin-1-yl)ethyl]-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1CCN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 IPBSBUQDPNMEBC-UHFFFAOYSA-N 0.000 description 1
- ZPIIXSDYIGOAEK-UHFFFAOYSA-N 3-[2-(4-benzhydrylpiperazin-1-yl)ethyl]-6-(trifluoromethyl)-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC(C(F)(F)F)=CC=C2N1CCN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 ZPIIXSDYIGOAEK-UHFFFAOYSA-N 0.000 description 1
- KMCHRZXDYUEYGN-UHFFFAOYSA-N 3-[2-(4-benzylpiperazin-1-yl)ethyl]-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1CCN(CC1)CCN1CC1=CC=CC=C1 KMCHRZXDYUEYGN-UHFFFAOYSA-N 0.000 description 1
- LVDMYTHNPRJUFI-UHFFFAOYSA-N 3-[2-nitro-4-(trifluoromethyl)anilino]propan-1-ol Chemical compound OCCCNC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O LVDMYTHNPRJUFI-UHFFFAOYSA-N 0.000 description 1
- ZEBMGFPBCFHVFV-UHFFFAOYSA-N 3-[3-(4-benzhydryloxypiperidin-1-yl)propyl]-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1CCCN(CC1)CCC1OC(C=1C=CC=CC=1)C1=CC=CC=C1 ZEBMGFPBCFHVFV-UHFFFAOYSA-N 0.000 description 1
- PARKUCOPVUPEMZ-UHFFFAOYSA-N 3-[3-(4-benzhydrylpiperazin-1-yl)propyl]-5,6-dichloro-1h-benzimidazol-2-one Chemical compound C1=2C=C(Cl)C(Cl)=CC=2NC(=O)N1CCCN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 PARKUCOPVUPEMZ-UHFFFAOYSA-N 0.000 description 1
- WYRFPHFAOFQJKO-UHFFFAOYSA-N 3-[3-(4-benzhydrylpiperazin-1-yl)propyl]-6-(trifluoromethyl)-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC(C(F)(F)F)=CC=C2N1CCCN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 WYRFPHFAOFQJKO-UHFFFAOYSA-N 0.000 description 1
- MBLQZVXRLQRJFJ-UHFFFAOYSA-N 3-[3-(4-benzhydrylpiperazin-1-yl)propyl]-n-methyl-2-oxobenzimidazole-1-carboxamide Chemical compound O=C1N(C(=O)NC)C2=CC=CC=C2N1CCCN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 MBLQZVXRLQRJFJ-UHFFFAOYSA-N 0.000 description 1
- GENSZJUUSFRMKN-UHFFFAOYSA-N 3-[3-(4-benzylpiperazin-1-yl)propyl]-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1CCCN(CC1)CCN1CC1=CC=CC=C1 GENSZJUUSFRMKN-UHFFFAOYSA-N 0.000 description 1
- ZLFPDFXNWOADGJ-UHFFFAOYSA-N 3-[3-[4-[phenyl(pyridin-2-yl)methyl]piperazin-1-yl]propyl]-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1CCCN(CC1)CCN1C(C=1N=CC=CC=1)C1=CC=CC=C1 ZLFPDFXNWOADGJ-UHFFFAOYSA-N 0.000 description 1
- OLMNLICXEKLQDC-UHFFFAOYSA-N 3-[5-(4-benzhydrylpiperazin-1-yl)pentyl]-1h-benzimidazol-2-one;hydrate;dihydrochloride Chemical compound O.Cl.Cl.O=C1NC2=CC=CC=C2N1CCCCCN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 OLMNLICXEKLQDC-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
- AUGPRLHZAOPVIR-UHFFFAOYSA-N 3-benzyl-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1CC1=CC=CC=C1 AUGPRLHZAOPVIR-UHFFFAOYSA-N 0.000 description 1
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 1
- OZWMGNZLBIUWBG-UHFFFAOYSA-N 4-(3-hydroxypropyl)benzimidazol-2-one Chemical compound OCCCC1=CC=CC2=NC(N=C21)=O OZWMGNZLBIUWBG-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- UYNCPUVPRZTEJS-UHFFFAOYSA-N 4-chloro-3-(3-chloropropyl)-1h-benzimidazol-2-one Chemical compound C1=CC=C2NC(=O)N(CCCCl)C2=C1Cl UYNCPUVPRZTEJS-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
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 206010013975 Dyspnoeas Diseases 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-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
- 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 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 208000008238 Muscle Spasticity Diseases 0.000 description 1
- 238000007126 N-alkylation reaction Methods 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 238000010934 O-alkylation reaction Methods 0.000 description 1
- OOQJLBPCGZWYJA-UHFFFAOYSA-N OC(=O)C(O)=O.C1=CC(OC)=CC=C1C(C=1C=CC(F)=CC=1)N1CCNCC1 Chemical compound OC(=O)C(O)=O.C1=CC(OC)=CC=C1C(C=1C=CC(F)=CC=1)N1CCNCC1 OOQJLBPCGZWYJA-UHFFFAOYSA-N 0.000 description 1
- FDXXIDZWTQRPJT-UHFFFAOYSA-N OC(=O)C(O)=O.FC1=CC=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 Chemical compound OC(=O)C(O)=O.FC1=CC=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 FDXXIDZWTQRPJT-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001361 allenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000002052 anaphylactic effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- FKPSBYZGRQJIMO-UHFFFAOYSA-M benzyl(triethyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC1=CC=CC=C1 FKPSBYZGRQJIMO-UHFFFAOYSA-M 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 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
- 230000037396 body weight Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000039 congener Substances 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 description 1
- ONPIGXOVMNUZEY-UHFFFAOYSA-N ethyl 4-benzhydryloxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1OC(C=1C=CC=CC=1)C1=CC=CC=C1 ONPIGXOVMNUZEY-UHFFFAOYSA-N 0.000 description 1
- QABJNOSERNVHDY-UHFFFAOYSA-N ethyl 4-hydroxypiperidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(O)CC1 QABJNOSERNVHDY-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000010855 food raising agent Nutrition 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000007031 hydroxymethylation reaction Methods 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000004694 iodide salts Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910001511 metal iodide Inorganic materials 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- NTEHWJBQADMGCG-UHFFFAOYSA-N n,n-dimethylformamide;nitrobenzene Chemical compound CN(C)C=O.[O-][N+](=O)C1=CC=CC=C1 NTEHWJBQADMGCG-UHFFFAOYSA-N 0.000 description 1
- YENBVILCORBTFP-UHFFFAOYSA-N n-(2-chloroethyl)-2-nitro-4-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1NCCCl YENBVILCORBTFP-UHFFFAOYSA-N 0.000 description 1
- PHKYIHLWOACFBT-UHFFFAOYSA-N n-(3-chloropropyl)-2-nitro-4-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1NCCCCl PHKYIHLWOACFBT-UHFFFAOYSA-N 0.000 description 1
- WOFRVOOYNJVVIK-UHFFFAOYSA-N n-(3-chloropropyl)-2-nitroaniline Chemical compound [O-][N+](=O)C1=CC=CC=C1NCCCCl WOFRVOOYNJVVIK-UHFFFAOYSA-N 0.000 description 1
- KJQNAIWETOXIFK-UHFFFAOYSA-N n-(3-chloropropyl)-2-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)NCCCCl KJQNAIWETOXIFK-UHFFFAOYSA-N 0.000 description 1
- ZSCRRJYCYYNNBD-UHFFFAOYSA-N n-[2-(4-benzhydrylpiperazin-1-yl)ethyl]-2-nitro-4-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1NCCN1CCN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 ZSCRRJYCYYNNBD-UHFFFAOYSA-N 0.000 description 1
- PPHFZNBXYVCFHS-UHFFFAOYSA-N n-[3-(4-benzhydrylpiperazin-1-yl)propyl]-2-nitro-4-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1NCCCN1CCN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 PPHFZNBXYVCFHS-UHFFFAOYSA-N 0.000 description 1
- VZVZOOZEOZJTTE-UHFFFAOYSA-N n-[3-(4-benzhydrylpiperazin-1-yl)propyl]-4,5-dichloro-2-nitroaniline Chemical compound [O-][N+](=O)C1=CC(Cl)=C(Cl)C=C1NCCCN1CCN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 VZVZOOZEOZJTTE-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 229960002698 oxatomide Drugs 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000036316 preload Effects 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 208000018198 spasticity Diseases 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 229960005137 succinic acid Drugs 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
-
- 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- 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
-
- 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
- C07D235/08—Radicals containing only hydrogen and carbon atoms
-
- 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
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- 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
-
- 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
- C07D235/28—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US67291976A | 1976-04-02 | 1976-04-02 | |
US75306276A | 1976-12-21 | 1976-12-21 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS52122380A JPS52122380A (en) | 1977-10-14 |
JPS6231707B2 true JPS6231707B2 (el) | 1987-07-09 |
Family
ID=27100846
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP3556077A Granted JPS52122380A (en) | 1976-04-02 | 1977-03-31 | Novel piperazine and piperidine derivative |
Country Status (31)
Country | Link |
---|---|
JP (1) | JPS52122380A (el) |
AT (1) | AT357541B (el) |
AU (1) | AU515173B2 (el) |
BG (1) | BG36044A3 (el) |
CA (1) | CA1097646A (el) |
CH (1) | CH634317A5 (el) |
CS (1) | CS191337B2 (el) |
CY (1) | CY1210A (el) |
DE (1) | DE2714437A1 (el) |
DK (1) | DK153477C (el) |
EG (1) | EG12722A (el) |
ES (1) | ES456690A1 (el) |
FI (1) | FI66178C (el) |
FR (1) | FR2346350A1 (el) |
GB (1) | GB1579365A (el) |
GR (1) | GR62465B (el) |
HU (1) | HU179491B (el) |
IE (1) | IE44942B1 (el) |
IL (1) | IL51797A (el) |
IT (1) | IT1086841B (el) |
KE (1) | KE3338A (el) |
LU (1) | LU77052A1 (el) |
MY (1) | MY8400208A (el) |
NL (1) | NL190522C (el) |
NO (1) | NO146774C (el) |
NZ (1) | NZ183506A (el) |
PH (1) | PH12951A (el) |
PT (1) | PT66384B (el) |
SE (1) | SE431333B (el) |
SU (1) | SU683621A3 (el) |
YU (1) | YU39992B (el) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4181802A (en) * | 1978-05-11 | 1980-01-01 | Janssen Pharmaceutica N.V. | 1-(Heterocyclylalkyl)-1,3-dihydro-2-H-benzimidazole-2-ones |
US4254127A (en) * | 1980-04-03 | 1981-03-03 | Janssen Pharmaceutica, N.V. | 1,3-Dihydro-1-[(1-piperidinyl)alkyl]-2H-benzimidazol-2-one derivatives |
JPS57106663A (en) * | 1980-12-23 | 1982-07-02 | Kyorin Pharmaceut Co Ltd | 1,4-disubstituted piperazine derivative and its preparation |
ES514340A0 (es) * | 1982-06-17 | 1983-09-01 | Ferrer Int | "procedimiento de obtencion de nuevos derivados de piperazina". |
DE3442757A1 (de) * | 1984-11-23 | 1986-05-28 | Wella Ag, 6100 Darmstadt | Verwendung von 2-nitroanilinderivaten in haarfaerbemitteln und neue 2-nitroanilinderivate |
JPS625956A (ja) * | 1985-07-02 | 1987-01-12 | Terumo Corp | ビニル誘導体およびこれを含有する5−リポキシゲナ−ゼ作用阻害剤 |
FR2635524B1 (fr) * | 1988-08-19 | 1992-04-24 | Adir | Nouveaux derives de benzopyrrolidinone, leur procede de preparation et les compositions pharmaceutiques les renfermant |
US5169855A (en) * | 1990-03-28 | 1992-12-08 | Du Pont Merck Pharmaceutical Company | Piperidine ether derivatives as psychotropic drugs or plant fungicides |
IT1251144B (it) * | 1991-07-30 | 1995-05-04 | Boehringer Ingelheim Italia | Derivati del benzimidazolone |
ES2118255T3 (es) * | 1992-03-23 | 1998-09-16 | Janssen Pharmaceutica Nv | Agente para uso como antiirritante. |
ES2115709T3 (es) * | 1992-11-29 | 1998-07-01 | Clariant Gmbh | Nuevas benzofenonas halogenadas asimetricas, y procedimiento para su preparacion. |
US5883094A (en) * | 1995-04-24 | 1999-03-16 | Pfizer Inc. | Benzimidazolone derivatives with central dopaminergic activity |
US5889010A (en) * | 1995-05-18 | 1999-03-30 | Pfizer Inc. | Benzimidazole derivatives having dopaminergic activity |
IT1292409B1 (it) * | 1997-06-24 | 1999-02-08 | Bidachem Spa | Procedimento per la preparazione di oxatomide |
GB0009479D0 (en) * | 2000-04-17 | 2000-06-07 | Cipla Limited | Antihistaminic compounds |
WO2002024661A2 (en) * | 2000-09-19 | 2002-03-28 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | New n, n'-disubstituted benzimidazolone derivatives with affinity at the serotonin and dopamine receptors |
US6939887B2 (en) | 2001-01-30 | 2005-09-06 | Sumitomo Pharmaceuticals Co., Ltd. | Benzimidazolidinone derivatives |
US20070173486A1 (en) * | 2003-05-01 | 2007-07-26 | Vernalis Research Limited | Azetidinecarboxamide derivatives and their use in the treatment of cb1 receptor mediated disordrs |
MY150958A (en) * | 2005-06-16 | 2014-03-31 | Astrazeneca Ab | Compounds for the treatment of multi-drug resistant bacterial infections |
EP2024364A1 (en) * | 2006-05-26 | 2009-02-18 | Neuromed Pharmaceuticals, Ltd. | Heterocyclic compounds as calcium channel blockers |
WO2010128516A2 (en) * | 2009-05-04 | 2010-11-11 | Symed Labs Limited | Process for the preparation of flibanserin involving novel intermediates |
CN104926734B (zh) * | 2015-07-07 | 2017-04-05 | 苏州立新制药有限公司 | 氟班色林的制备方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2882271A (en) * | 1959-04-14 | Xcixcxh | ||
US3362956A (en) * | 1965-08-19 | 1968-01-09 | Sterling Drug Inc | 1-[(heterocyclyl)-lower-alkyl]-4-substituted-piperazines |
US3369022A (en) * | 1966-11-07 | 1968-02-13 | Robins Co Inc A H | 3-piperazinoalkyl-2-benzoxazolinones |
JPS5070389A (el) * | 1973-10-30 | 1975-06-11 |
-
1977
- 1977-03-02 YU YU566/77A patent/YU39992B/xx unknown
- 1977-03-04 NZ NZ183506A patent/NZ183506A/xx unknown
- 1977-03-09 ES ES456690A patent/ES456690A1/es not_active Expired
- 1977-03-10 FR FR7707106A patent/FR2346350A1/fr active Granted
- 1977-03-14 GR GR52987A patent/GR62465B/el unknown
- 1977-03-14 BG BG035664A patent/BG36044A3/xx unknown
- 1977-03-18 CA CA274,240A patent/CA1097646A/en not_active Expired
- 1977-03-24 CS CS771972A patent/CS191337B2/cs unknown
- 1977-03-25 GB GB12754/77A patent/GB1579365A/en not_active Expired
- 1977-03-25 CY CY1210A patent/CY1210A/xx unknown
- 1977-03-30 EG EG180/77A patent/EG12722A/xx active
- 1977-03-31 AU AU23824/77A patent/AU515173B2/en not_active Expired
- 1977-03-31 IL IL51797A patent/IL51797A/xx unknown
- 1977-03-31 IT IT48768/77A patent/IT1086841B/it active
- 1977-03-31 LU LU77052A patent/LU77052A1/xx unknown
- 1977-03-31 DE DE19772714437 patent/DE2714437A1/de active Granted
- 1977-03-31 JP JP3556077A patent/JPS52122380A/ja active Granted
- 1977-04-01 CH CH415477A patent/CH634317A5/de not_active IP Right Cessation
- 1977-04-01 FI FI771020A patent/FI66178C/fi not_active IP Right Cessation
- 1977-04-01 PT PT66384A patent/PT66384B/pt unknown
- 1977-04-01 HU HU77JA782A patent/HU179491B/hu unknown
- 1977-04-01 DK DK145977A patent/DK153477C/da not_active IP Right Cessation
- 1977-04-01 PH PH19620A patent/PH12951A/en unknown
- 1977-04-01 NO NO771168A patent/NO146774C/no unknown
- 1977-04-01 SU SU772468056A patent/SU683621A3/ru active
- 1977-04-01 AT AT230477A patent/AT357541B/de not_active IP Right Cessation
- 1977-04-01 SE SE7703842A patent/SE431333B/xx not_active IP Right Cessation
- 1977-04-01 IE IE699/77A patent/IE44942B1/en not_active IP Right Cessation
- 1977-04-01 NL NLAANVRAGE7703564,A patent/NL190522C/xx not_active IP Right Cessation
-
1983
- 1983-10-24 KE KE3338A patent/KE3338A/xx unknown
-
1984
- 1984-12-30 MY MY208/84A patent/MY8400208A/xx unknown
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JPS6231707B2 (el) | ||
US4200641A (en) | 1-[(Heterocyclyl)-alkyl]-4-diarylmethoxy piperidine derivatives | |
AU646519B2 (en) | Pyridine and pyridine N-oxide derivatives of diaryl methyl piperidines or piperazines, and compositions and methods of use thereof | |
US6441000B1 (en) | Compounds useful in therapy | |
US4250176A (en) | Piperazine derivatives | |
JPH0794393B2 (ja) | N−複素環式−4−ピペリジンアミン類を含有している抗−ヒスタミン組成物類 | |
JPH0524151B2 (el) | ||
SK70899A3 (en) | 6-phenylpyridyl-2-amine derivatives useful as nos inhibitors | |
US4835161A (en) | Anti-histaminic compositions containing n-heterocyclyl-4-piperidinamines | |
US4243806A (en) | 5-[4-(Diarylmethyl)-1-piperazinylalkyl]benzimidazole derivatives | |
US4179505A (en) | 5-[4-(Diarylmethyl)-1-piperazinylalkyl]benzimidazole derivatives | |
JPH0460596B2 (el) | ||
US4632925A (en) | N-substituted diphenylpiperidines and antiobesity use thereof | |
JP2574377B2 (ja) | 睡眠改善剤 | |
JPH0215550B2 (el) | ||
US4377578A (en) | Piperazine derivatives | |
JPH01228986A (ja) | [(5(6)(1h―アゾール―1―イルメチル)ベンズイミダゾール]カーバメート | |
JP2512755B2 (ja) | 4−(アロイルアミノ)ピペリジンブタンアミド誘導体 | |
JP2954992B2 (ja) | 抗精神病性化合物類 | |
IE49526B1 (en) | Phenyl piperazine derivatives,their preparation and antiagressive medicines containing them | |
RU2123001C1 (ru) | N - оксиды 4-фенилпиперазинов и 4-фенилпиперидинов, композиция на их основе и способ ингибирования допамин-2 рецепторов | |
JPS6230990B2 (el) | ||
JPH0625151B2 (ja) | 2−置換シクロヘプトイミダゾ−ル誘導体、抗潰瘍剤及びその製造方法 | |
EP0269383A2 (en) | 1-Aryloxy-4-[(4-aryl)-1-piperazinyl]-2-butanols useful as antiallergy agents | |
KR810000711B1 (ko) | 피페라진 또는 피페리딘 유도체의 제조방법 |