CY1253A - N-phenyl-n-(4-piperidinyl)-amides - Google Patents
N-phenyl-n-(4-piperidinyl)-amides Download PDFInfo
- Publication number
- CY1253A CY1253A CY1253A CY125378A CY1253A CY 1253 A CY1253 A CY 1253A CY 1253 A CY1253 A CY 1253A CY 125378 A CY125378 A CY 125378A CY 1253 A CY1253 A CY 1253A
- Authority
- CY
- Cyprus
- Prior art keywords
- tetrazol
- dihydro
- ethyl
- methyl
- piperidinyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- -1 N - (1 - [2 - (4 - Ethyl - 4,5 - dihydro - 5 - oxo - 1H - tetrazol - 1 - yl)-ethyl] - 4 - (methoxymethyl) - piperidinyl} - N - phenylpropanamide Chemical compound 0.000 claims description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims description 15
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 150000003254 radicals Chemical group 0.000 claims description 9
- ZTHRQJQJODGZHV-UHFFFAOYSA-N N-phenyl-propionamide Natural products CCC(=O)NC1=CC=CC=C1 ZTHRQJQJODGZHV-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- YVVZUMUVGRLSRZ-UHFFFAOYSA-N 1-ethyl-2h-tetrazol-5-one Chemical compound CCN1NN=NC1=O YVVZUMUVGRLSRZ-UHFFFAOYSA-N 0.000 claims description 7
- 230000000202 analgesic effect Effects 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- CKOJGMKAXXTOLV-UHFFFAOYSA-N 1-(2-chloroethyl)-4-ethyltetrazol-5-one Chemical compound CCN1N=NN(CCCl)C1=O CKOJGMKAXXTOLV-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- ULOZGJWEIWAWML-UHFFFAOYSA-N Noralfentanil Chemical compound C1CNCCC1(COC)N(C(=O)CC)C1=CC=CC=C1 ULOZGJWEIWAWML-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- LKRMTUUCKBQGFO-UHFFFAOYSA-N n-phenylpiperidin-4-amine Chemical class C1CNCCC1NC1=CC=CC=C1 LKRMTUUCKBQGFO-UHFFFAOYSA-N 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 230000006181 N-acylation Effects 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005002 aryl methyl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 7
- BKHYJILOADVNME-UHFFFAOYSA-N n-[1-[1-(4-ethyl-5-oxotetrazol-1-yl)propan-2-yl]-4-(methoxymethyl)piperidin-4-yl]-n-phenylpropanamide Chemical compound C1CN(C(C)CN2C(N(CC)N=N2)=O)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 BKHYJILOADVNME-UHFFFAOYSA-N 0.000 claims 2
- 239000013256 coordination polymer Substances 0.000 claims 1
- 238000006264 debenzylation reaction Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- OHAKVFPGXHKSME-UHFFFAOYSA-N methyl 4-(n-propanoylanilino)piperidine-4-carboxylate;hydrochloride Chemical compound Cl.C1CNCCC1(C(=O)OC)N(C(=O)CC)C1=CC=CC=C1 OHAKVFPGXHKSME-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000003480 eluent Substances 0.000 description 21
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 21
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 239000007858 starting material Substances 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 229960001701 chloroform Drugs 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 5
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 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 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- WLGREALAOVWKDB-UHFFFAOYSA-N 1-(2-iodoethyl)-4-methyltetrazol-5-one Chemical compound CN1N=NN(CCI)C1=O WLGREALAOVWKDB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-L Oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 description 3
- 150000001263 acyl chlorides Chemical class 0.000 description 3
- 229940035676 analgesics Drugs 0.000 description 3
- 239000000730 antalgic agent Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 3
- PHVQENBNTDWRJW-UHFFFAOYSA-N 1-(2-chloroethyl)-2h-tetrazol-5-one Chemical compound ClCCN1N=NNC1=O PHVQENBNTDWRJW-UHFFFAOYSA-N 0.000 description 2
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 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
- 241001465754 Metazoa Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- 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 2
- 239000000969 carrier Substances 0.000 description 2
- 125000004965 chloroalkyl group Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000002346 iodo group Chemical group I* 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- PDZXSAYPYXZTPZ-UHFFFAOYSA-N n-[1-(2-chloropropyl)-4-(methoxymethyl)piperidin-4-yl]-n-phenylpropanamide;hydrochloride Chemical compound Cl.C1CN(CC(C)Cl)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 PDZXSAYPYXZTPZ-UHFFFAOYSA-N 0.000 description 2
- IVLIEQUZEPVOHH-UHFFFAOYSA-N n-[1-(2-hydroxypropyl)-4-(methoxymethyl)piperidin-4-yl]-n-phenylpropanamide;hydrochloride Chemical compound Cl.C1CN(CC(C)O)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 IVLIEQUZEPVOHH-UHFFFAOYSA-N 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
- BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- OUOJIFQQBPKAMU-UHFFFAOYSA-N tetrazol-5-one Chemical compound O=C1N=NN=N1 OUOJIFQQBPKAMU-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PTXFNAITKCOVFP-UHFFFAOYSA-N 1-(2-chloroethyl)-4-(2-phenylethyl)tetrazol-5-one Chemical compound O=C1N(CCCl)N=NN1CCC1=CC=CC=C1 PTXFNAITKCOVFP-UHFFFAOYSA-N 0.000 description 1
- JZRPAQBFQSCPAO-UHFFFAOYSA-N 1-(2-chloroethyl)-4-cyclohexyltetrazol-5-one Chemical compound O=C1N(CCCl)N=NN1C1CCCCC1 JZRPAQBFQSCPAO-UHFFFAOYSA-N 0.000 description 1
- ISLWBWXRZMZCFI-UHFFFAOYSA-N 1-(2-chloroethyl)-4-cyclopropyltetrazol-5-one Chemical compound O=C1N(CCCl)N=NN1C1CC1 ISLWBWXRZMZCFI-UHFFFAOYSA-N 0.000 description 1
- RTUHTRUUYHGXID-UHFFFAOYSA-N 1-(2-chloroethyl)-4-propan-2-yltetrazol-5-one Chemical compound CC(C)N1N=NN(CCCl)C1=O RTUHTRUUYHGXID-UHFFFAOYSA-N 0.000 description 1
- RTGOBOQFBFJTJZ-UHFFFAOYSA-N 1-(2-chloroethyl)-4-propyltetrazol-5-one Chemical compound CCCN1N=NN(CCCl)C1=O RTGOBOQFBFJTJZ-UHFFFAOYSA-N 0.000 description 1
- HAFBIGUYBLKUCD-UHFFFAOYSA-N 1-(2-phenylethyl)-2h-tetrazol-5-one Chemical compound O=C1NN=NN1CCC1=CC=CC=C1 HAFBIGUYBLKUCD-UHFFFAOYSA-N 0.000 description 1
- UJCZVKBDDPDWBN-UHFFFAOYSA-N 1-(3-chloropropyl)-4-ethyltetrazol-5-one Chemical compound CCN1N=NN(CCCCl)C1=O UJCZVKBDDPDWBN-UHFFFAOYSA-N 0.000 description 1
- SXRYBEHIRMBNAF-UHFFFAOYSA-N 1-benzyl-2h-tetrazol-5-one Chemical compound O=C1NN=NN1CC1=CC=CC=C1 SXRYBEHIRMBNAF-UHFFFAOYSA-N 0.000 description 1
- RFGMNHVXOIHQPZ-UHFFFAOYSA-N 1-cyclohexyl-2h-tetrazol-5-one Chemical compound O=C1NN=NN1C1CCCCC1 RFGMNHVXOIHQPZ-UHFFFAOYSA-N 0.000 description 1
- GUTNODKBPXZJOD-UHFFFAOYSA-N 1-cyclopropyl-2h-tetrazol-5-one Chemical compound O=C1NN=NN1C1CC1 GUTNODKBPXZJOD-UHFFFAOYSA-N 0.000 description 1
- QKFGKKCHXFAAKF-UHFFFAOYSA-N 1-pentyl-2h-tetrazol-5-one Chemical compound CCCCCN1N=NNC1=O QKFGKKCHXFAAKF-UHFFFAOYSA-N 0.000 description 1
- FYYACQQSYSDVJB-UHFFFAOYSA-N 1-phenyl-2h-tetrazol-5-one Chemical compound OC1=NN=NN1C1=CC=CC=C1 FYYACQQSYSDVJB-UHFFFAOYSA-N 0.000 description 1
- VWLKWKCGYOWRMJ-UHFFFAOYSA-N 1-propan-2-yl-2h-tetrazol-5-one Chemical compound CC(C)N1N=NNC1=O VWLKWKCGYOWRMJ-UHFFFAOYSA-N 0.000 description 1
- WBWJLLBFGAVACI-UHFFFAOYSA-N 1-propyl-2h-tetrazol-5-one Chemical compound CCCN1N=NNC1=O WBWJLLBFGAVACI-UHFFFAOYSA-N 0.000 description 1
- RFTHNPDGSJBHMR-UHFFFAOYSA-N 1-tert-butyl-2h-tetrazol-5-one Chemical compound CC(C)(C)N1N=NNC1=O RFTHNPDGSJBHMR-UHFFFAOYSA-N 0.000 description 1
- VQLDASBRCVENRK-UHFFFAOYSA-N 1-tert-butyl-4-(2-chloroethyl)tetrazol-5-one Chemical compound CC(C)(C)N1N=NN(CCCl)C1=O VQLDASBRCVENRK-UHFFFAOYSA-N 0.000 description 1
- JXBKZAYVMSNKHA-UHFFFAOYSA-N 1h-tetrazol-1-ium-5-olate Chemical compound OC=1N=NNN=1 JXBKZAYVMSNKHA-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 1
- ALFXFSIISQANBR-UHFFFAOYSA-N 2-phenylpropanamide;hydrochloride Chemical compound Cl.NC(=O)C(C)C1=CC=CC=C1 ALFXFSIISQANBR-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- HLPRKWVEMYDPAU-UHFFFAOYSA-N 2-thiophen-2-ylethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCC1=CC=CS1 HLPRKWVEMYDPAU-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
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- KBIWNQVZKHSHTI-UHFFFAOYSA-N 4-n,4-n-dimethylbenzene-1,4-diamine;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)C1=CC=C(N)C=C1 KBIWNQVZKHSHTI-UHFFFAOYSA-N 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- QFOCKLXLYKLACU-UHFFFAOYSA-N OC(=O)C(O)=O.O=C1N(CCC)N=NN1CCN1CCC(COC)(N(C(=O)CC)C=2C=CC=CC=2)CC1 Chemical compound OC(=O)C(O)=O.O=C1N(CCC)N=NN1CCN1CCC(COC)(N(C(=O)CC)C=2C=CC=CC=2)CC1 QFOCKLXLYKLACU-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- IUKQLMGVFMDQDP-UHFFFAOYSA-N azane;piperidine Chemical compound N.C1CCNCC1 IUKQLMGVFMDQDP-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides 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
- 239000011230 binding agent Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 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
- 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
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 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
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000002367 halogens Chemical class 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
- NVUYWKBRSRPYMH-UHFFFAOYSA-N hydron;piperidine-4-carboxylic acid;chloride Chemical compound Cl.OC(=O)C1CCNCC1 NVUYWKBRSRPYMH-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates 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
- 239000000314 lubricant Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- VZFOKDQSIKOPIB-UHFFFAOYSA-N methyl 1-[2-(5-oxo-4-propan-2-yltetrazol-1-yl)ethyl]-4-(N-propanoylanilino)piperidine-4-carboxylate oxalic acid Chemical compound OC(=O)C(O)=O.C1CN(CCN2C(N(C(C)C)N=N2)=O)CCC1(C(=O)OC)N(C(=O)CC)C1=CC=CC=C1 VZFOKDQSIKOPIB-UHFFFAOYSA-N 0.000 description 1
- ARBRDZRQUWKCLC-UHFFFAOYSA-N methyl 4-[n-(cyclopropanecarbonyl)anilino]-1-[2-(4-ethyl-5-oxotetrazol-1-yl)ethyl]piperidine-4-carboxylate;oxalic acid Chemical compound OC(=O)C(O)=O.O=C1N(CC)N=NN1CCN1CCC(C(=O)OC)(N(C(=O)C2CC2)C=2C=CC=CC=2)CC1 ARBRDZRQUWKCLC-UHFFFAOYSA-N 0.000 description 1
- LYWCFOFXHMCRFT-UHFFFAOYSA-N methyl 4-anilino-1-[2-(4-ethyl-5-oxotetrazol-1-yl)ethyl]piperidine-4-carboxylate Chemical compound O=C1N(CC)N=NN1CCN1CCC(C(=O)OC)(NC=2C=CC=CC=2)CC1 LYWCFOFXHMCRFT-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- FLGJQVIXZNBCJZ-UHFFFAOYSA-N n-[1-(2-chloropropyl)-4-(methoxymethyl)piperidin-4-yl]-n-phenylpropanamide Chemical compound C1CN(CC(C)Cl)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 FLGJQVIXZNBCJZ-UHFFFAOYSA-N 0.000 description 1
- CKGXIGKMYMSTRC-UHFFFAOYSA-N n-[1-(2-hydroxy-2-phenylethyl)-4-(methoxymethyl)piperidin-4-yl]-n-phenylpropanamide;hydrochloride Chemical compound Cl.C1CN(CC(O)C=2C=CC=CC=2)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 CKGXIGKMYMSTRC-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- FGHSTPNOXKDLKU-UHFFFAOYSA-N nitric acid;hydrate Chemical compound O.O[N+]([O-])=O FGHSTPNOXKDLKU-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 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
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 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
- 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
- 125000004523 tetrazol-1-yl group Chemical group N1(N=NN=C1)* 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79381477A | 1977-05-05 | 1977-05-05 | |
| US88618878A | 1978-03-13 | 1978-03-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CY1253A true CY1253A (en) | 1984-08-31 |
Family
ID=27121432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CY1253A CY1253A (en) | 1977-05-05 | 1978-05-03 | N-phenyl-n-(4-piperidinyl)-amides |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS53149980A (en)) |
| AT (1) | AT368994B (en)) |
| AU (1) | AU514360B2 (en)) |
| CA (1) | CA1105464A (en)) |
| CH (1) | CH635585A5 (en)) |
| CY (1) | CY1253A (en)) |
| DE (1) | DE2819873A1 (en)) |
| DK (1) | DK152211C (en)) |
| ES (1) | ES469473A1 (en)) |
| FI (1) | FI64364C (en)) |
| FR (1) | FR2389622B1 (en)) |
| GB (1) | GB1598872A (en)) |
| HK (1) | HK72585A (en)) |
| HU (1) | HU179204B (en)) |
| IE (1) | IE46836B1 (en)) |
| IL (1) | IL54639A (en)) |
| IT (1) | IT1105288B (en)) |
| KE (1) | KE3429A (en)) |
| LU (1) | LU79575A1 (en)) |
| NL (1) | NL186861C (en)) |
| NO (1) | NO148747C (en)) |
| NZ (1) | NZ187164A (en)) |
| PH (1) | PH12831A (en)) |
| SE (1) | SE437516B (en)) |
| SU (1) | SU867304A3 (en)) |
| YU (1) | YU40703B (en)) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6144294A (ja) * | 1984-08-07 | 1986-03-03 | Nippon Denso Co Ltd | 熱交換器 |
| US5053411A (en) * | 1989-04-20 | 1991-10-01 | Anaquest, Inc. | N-aryl-N-[4-(1-heterocyclicalkyl)piperidinyl]amides and pharmaceutical compositions and methods employing such compounds |
| USRE34201E (en) * | 1989-04-20 | 1993-03-23 | Anaquest, Inc. | N-aryl-N-[4-(1-heterocyclicalkyl)piperidinyl]amides and pharmaceutical compositions and methods employing such compounds |
| JPH08193074A (ja) * | 1994-11-18 | 1996-07-30 | Nippon Bayeragrochem Kk | 除草性１−シクロプロピルテトラゾリノン類 |
| RU2144533C1 (ru) * | 1994-12-09 | 2000-01-20 | Такеда Кемикал Индастриз, Лтд. | Производные тетразола, способ их получения и фармацевтические композиции на их основе |
| JP2000327668A (ja) * | 1999-05-21 | 2000-11-28 | Nippon Bayer Agrochem Co Ltd | テトラゾリノン誘導体 |
| CA2393559C (en) * | 1999-12-06 | 2009-05-26 | Mallinckrodt Inc. | Methods for the syntheses of alfentanil, sufentanil and remifentanil |
| US20090030041A1 (en) * | 2004-09-14 | 2009-01-29 | Toshihiro Takahashi | N-substituted N-(4-piperidinyl) Amide Derivative |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3998834A (en) * | 1975-03-14 | 1976-12-21 | Janssen Pharmaceutica N.V. | N-(4-piperidinyl)-n-phenylamides and -carbamates |
-
1978
- 1978-04-24 FR FR7812084A patent/FR2389622B1/fr not_active Expired
- 1978-04-25 PH PH21055A patent/PH12831A/en unknown
- 1978-04-27 AU AU35522/78A patent/AU514360B2/en not_active Expired
- 1978-05-02 LU LU79575A patent/LU79575A1/xx unknown
- 1978-05-03 NO NO781559A patent/NO148747C/no unknown
- 1978-05-03 CY CY1253A patent/CY1253A/en unknown
- 1978-05-03 SE SE7805110A patent/SE437516B/sv not_active IP Right Cessation
- 1978-05-03 DK DK193778A patent/DK152211C/da not_active IP Right Cessation
- 1978-05-03 AT AT0322078A patent/AT368994B/de not_active IP Right Cessation
- 1978-05-03 GB GB17566/78A patent/GB1598872A/en not_active Expired
- 1978-05-03 NZ NZ187164A patent/NZ187164A/xx unknown
- 1978-05-04 FI FI781398A patent/FI64364C/fi not_active IP Right Cessation
- 1978-05-04 CA CA302,616A patent/CA1105464A/en not_active Expired
- 1978-05-04 IE IE901/78A patent/IE46836B1/en not_active IP Right Cessation
- 1978-05-04 HU HU78JA819A patent/HU179204B/hu unknown
- 1978-05-04 JP JP5287378A patent/JPS53149980A/ja active Granted
- 1978-05-04 ES ES469473A patent/ES469473A1/es not_active Expired
- 1978-05-04 IL IL54639A patent/IL54639A/xx unknown
- 1978-05-04 IT IT49203/78A patent/IT1105288B/it active
- 1978-05-05 NL NLAANVRAGE7804844,A patent/NL186861C/xx not_active IP Right Cessation
- 1978-05-05 SU SU782613447A patent/SU867304A3/ru active
- 1978-05-05 DE DE19782819873 patent/DE2819873A1/de active Granted
- 1978-05-05 CH CH492478A patent/CH635585A5/de not_active IP Right Cessation
- 1978-05-05 YU YU1085/78A patent/YU40703B/xx unknown
-
1984
- 1984-07-20 KE KE3429A patent/KE3429A/xx unknown
-
1985
- 1985-09-26 HK HK725/85A patent/HK72585A/en not_active IP Right Cessation
Also Published As
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