DD147537A5 - Verfahren zur herstellung von 1,2,4,5-tetra-alkyl-4-aryl-piperidinen - Google Patents

Verfahren zur herstellung von 1,2,4,5-tetra-alkyl-4-aryl-piperidinen Download PDF

Info

Publication number: DD147537A5
Authority: DD; German Democratic Republic
Prior art keywords: methoxyphenyl; piperidine; formula; group; propyl
Prior art date: 1978-11-29

Application number

DD79217246A

Other languages

German (de)

English (en)

Inventor

Dennis M Zimmermann

Original Assignee

Lilly Co Eli

Priority date (The priority date 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 date listed.)

1978-11-29

Filing date

1979-11-29

Publication date

1981-04-08

1979-11-29 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1981-04-08 Publication of DD147537A5 publication Critical patent/DD147537A5/de

Links

238000002360 preparation method Methods 0.000 title claims abstract description 23
238000000034 method Methods 0.000 title claims abstract description 20
-1 1,4,5-trimethyl-4- (3-methoxyphenyl) -3,4,5,6-tetrahydropyridinium Chemical compound 0.000 claims abstract description 27
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 claims abstract description 8
VBXFHOUODKNPDY-UHFFFAOYSA-N 4-(3-methoxyphenyl)-1,2,4,5-tetramethylpiperidine Chemical compound COC1=CC=CC(C2(C)C(CN(C)C(C)C2)C)=C1 VBXFHOUODKNPDY-UHFFFAOYSA-N 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 37
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 32
125000004432 carbon atom Chemical group C* 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 13
229960000583 acetic acid Drugs 0.000 claims description 12
150000007975 iminium salts Chemical class 0.000 claims description 12
239000002168 alkylating agent Substances 0.000 claims description 10
229940100198 alkylating agent Drugs 0.000 claims description 10
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 8
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
150000001450 anions Chemical class 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
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
239000012362 glacial acetic acid Substances 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
FMMBOHMPGQFMRW-UHFFFAOYSA-N 3-(1,2,5-trimethyl-4-propylpiperidin-4-yl)phenol Chemical compound C=1C=CC(O)=CC=1C1(CCC)CC(C)N(C)CC1C FMMBOHMPGQFMRW-UHFFFAOYSA-N 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
WEEHXWRDZCHKQB-UHFFFAOYSA-N 3-(1,2,4,5-tetramethylpiperidin-4-yl)phenol Chemical compound CC1CN(C)C(C)CC1(C)C1=CC=CC(O)=C1 WEEHXWRDZCHKQB-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
238000005661 deetherification reaction Methods 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 43
239000011541 reaction mixture Substances 0.000 abstract description 13
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract description 8
230000000202 analgesic effect Effects 0.000 abstract description 8
210000003169 central nervous system Anatomy 0.000 abstract description 5
235000019270 ammonium chloride Nutrition 0.000 abstract description 4
239000012044 organic layer Substances 0.000 abstract description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000002904 solvent Substances 0.000 description 13
239000000243 solution Substances 0.000 description 11
150000003053 piperidines Chemical class 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
238000005804 alkylation reaction Methods 0.000 description 8
239000000047 product Substances 0.000 description 8
241001465754 Metazoa Species 0.000 description 7
238000004458 analytical method Methods 0.000 description 7
239000002585 base Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
230000029936 alkylation Effects 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
230000036407 pain Effects 0.000 description 6
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
125000003386 piperidinyl group Chemical group 0.000 description 6
239000007858 starting material Substances 0.000 description 6
VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical class C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 5
125000001118 alkylidene group Chemical group 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
238000001914 filtration Methods 0.000 description 5
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
241000699666 Mus <mouse, genus> Species 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
238000004821 distillation Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
229940093915 gynecological organic acid Drugs 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
239000011976 maleic acid Substances 0.000 description 4
150000007524 organic acids Chemical class 0.000 description 4
235000005985 organic acids Nutrition 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
FINLIMGQGJZNRN-UHFFFAOYSA-N 3-piperidin-4-ylphenol Chemical class OC1=CC=CC(C2CCNCC2)=C1 FINLIMGQGJZNRN-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000001640 fractional crystallisation Methods 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
238000007920 subcutaneous administration Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
XYUOSSGYQKXJJS-UHFFFAOYSA-N 1-benzyl-3,4-dimethyl-4-phenyl-2,3-dihydropyridine Chemical compound C1=CC(C=2C=CC=CC=2)(C)C(C)CN1CC1=CC=CC=C1 XYUOSSGYQKXJJS-UHFFFAOYSA-N 0.000 description 2
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 2
XOVRMTNLUARRFP-UHFFFAOYSA-N 4-(3-methoxyphenyl)-1,2,5-trimethyl-4-propylpiperidine Chemical compound C=1C=CC(OC)=CC=1C1(CCC)CC(C)N(C)CC1C XOVRMTNLUARRFP-UHFFFAOYSA-N 0.000 description 2
NKHVIQNRNSVKMJ-UHFFFAOYSA-N 4-(3-methoxyphenyl)-1,3,4-trimethyl-2,3-dihydropyridine Chemical compound COC1=CC=CC(C2(C)C(CN(C)C=C2)C)=C1 NKHVIQNRNSVKMJ-UHFFFAOYSA-N 0.000 description 2
DBURUKHPZWMEGL-UHFFFAOYSA-N 4-(3-methoxyphenyl)-1,3-dimethyl-4-propyl-2,3-dihydropyridine Chemical compound C=1C=CC(OC)=CC=1C1(CCC)C=CN(C)CC1C DBURUKHPZWMEGL-UHFFFAOYSA-N 0.000 description 2
NONQCMNVMIGQEE-UHFFFAOYSA-N 4-(3-methoxyphenyl)piperidine Chemical class COC1=CC=CC(C2CCNCC2)=C1 NONQCMNVMIGQEE-UHFFFAOYSA-N 0.000 description 2
UTBULQCHEUWJNV-UHFFFAOYSA-N 4-phenylpiperidine Chemical class C1CNCCC1C1=CC=CC=C1 UTBULQCHEUWJNV-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000000556 agonist Substances 0.000 description 2
HFEHLDPGIKPNKL-UHFFFAOYSA-N allyl iodide Chemical compound ICC=C HFEHLDPGIKPNKL-UHFFFAOYSA-N 0.000 description 2
229940035676 analgesics Drugs 0.000 description 2
239000000730 antalgic agent Substances 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
125000004981 cycloalkylmethyl group Chemical group 0.000 description 2
238000010520 demethylation reaction Methods 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
150000002081 enamines Chemical class 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
239000012467 final product Substances 0.000 description 2
229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
238000002156 mixing Methods 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
229960000482 pethidine Drugs 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
230000007017 scission Effects 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
XYCHMYKPKLTNDM-UHFFFAOYSA-N (1-methyl-4-phenylpiperidin-3-yl)-phenylmethanone Chemical compound C1N(C)CCC(C=2C=CC=CC=2)C1C(=O)C1=CC=CC=C1 XYCHMYKPKLTNDM-UHFFFAOYSA-N 0.000 description 1
OCQAXYHNMWVLRH-QZTJIDSGSA-N (2r,3r)-2,3-dibenzoyl-2,3-dihydroxybutanedioic acid Chemical compound O=C([C@@](O)(C(=O)O)[C@](O)(C(O)=O)C(=O)C=1C=CC=CC=1)C1=CC=CC=C1 OCQAXYHNMWVLRH-QZTJIDSGSA-N 0.000 description 1
MLBIQPYSNYZFRY-KSBRXOFISA-N (z)-but-2-enedioate;4-(3-methoxyphenyl)-1,2,4,5-tetramethylpiperidin-1-ium Chemical compound [O-]C(=O)\C=C/C([O-])=O.COC1=CC=CC(C2(C)C(C[NH+](C)C(C)C2)C)=C1.COC1=CC=CC(C2(C)C(C[NH+](C)C(C)C2)C)=C1 MLBIQPYSNYZFRY-KSBRXOFISA-N 0.000 description 1
FXGXJLKILDSMQD-KSBRXOFISA-N (z)-but-2-enedioate;4-(3-methoxyphenyl)-1,2,5-trimethyl-4-propylpiperidin-1-ium Chemical compound [O-]C(=O)\C=C/C([O-])=O.C=1C=CC(OC)=CC=1C1(CCC)CC(C)[NH+](C)CC1C.C=1C=CC(OC)=CC=1C1(CCC)CC(C)[NH+](C)CC1C FXGXJLKILDSMQD-KSBRXOFISA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
WMOHLQJUKIAWNF-UHFFFAOYSA-N 1-(cyclopentylmethyl)-4-(3-methoxyphenyl)-4,5-dimethyl-2-pentylpiperidine Chemical compound CCCCCC1CC(C)(C=2C=C(OC)C=CC=2)C(C)CN1CC1CCCC1 WMOHLQJUKIAWNF-UHFFFAOYSA-N 0.000 description 1
KXCLFDRDKZWQHW-UHFFFAOYSA-N 1-(cyclopropylmethyl)-2,4,5-triethyl-4-(3-methoxyphenyl)piperidine Chemical compound CCC1CC(CC)(C=2C=C(OC)C=CC=2)C(CC)CN1CC1CC1 KXCLFDRDKZWQHW-UHFFFAOYSA-N 0.000 description 1
OWFBKOGGVIAGAP-UHFFFAOYSA-N 1-(cyclopropylmethyl)-4-ethyl-4-(3-methoxyphenyl)-3-methyl-2,3-dihydropyridine Chemical compound C1C(C)C(CC)(C=2C=C(OC)C=CC=2)C=CN1CC1CC1 OWFBKOGGVIAGAP-UHFFFAOYSA-N 0.000 description 1
KGEZVUWOCCCTPV-UHFFFAOYSA-N 1-benzyl-3,4-dimethyl-4-phenylpiperidine Chemical compound C1CC(C=2C=CC=CC=2)(C)C(C)CN1CC1=CC=CC=C1 KGEZVUWOCCCTPV-UHFFFAOYSA-N 0.000 description 1
BBWOVOWQWYITHA-UHFFFAOYSA-N 1-benzyl-4,5-dimethyl-4-phenyl-2-propylpiperidine Chemical compound CCCC1CC(C)(C=2C=CC=CC=2)C(C)CN1CC1=CC=CC=C1 BBWOVOWQWYITHA-UHFFFAOYSA-N 0.000 description 1
CVBBTZNGRZSTRG-UHFFFAOYSA-N 1-benzyl-4-phenyl-2,4,5-tripropylpiperidine Chemical compound CCCC1CC(CCC)(C=2C=CC=CC=2)C(CCC)CN1CC1=CC=CC=C1 CVBBTZNGRZSTRG-UHFFFAOYSA-N 0.000 description 1
XAOFMTDKQYEOES-UHFFFAOYSA-N 1-bromo-5-methylhexane Chemical compound CC(C)CCCCBr XAOFMTDKQYEOES-UHFFFAOYSA-N 0.000 description 1
DAYVQUNSUAMYMD-UHFFFAOYSA-N 1-ethyl-2-methyl-4-phenyl-4-propan-2-yl-5-propylpiperidine Chemical compound CCCC1CN(CC)C(C)CC1(C(C)C)C1=CC=CC=C1 DAYVQUNSUAMYMD-UHFFFAOYSA-N 0.000 description 1
SKIDNYUZJPMKFC-UHFFFAOYSA-N 1-iododecane Chemical compound CCCCCCCCCCI SKIDNYUZJPMKFC-UHFFFAOYSA-N 0.000 description 1
XEAFHQNWQVSWTE-UHFFFAOYSA-N 2,4,5-tributyl-1-decyl-4-phenylpiperidine Chemical compound C1C(CCCC)N(CCCCCCCCCC)CC(CCCC)C1(CCCC)C1=CC=CC=C1 XEAFHQNWQVSWTE-UHFFFAOYSA-N 0.000 description 1
ZRKIAUXZSJNVBA-UHFFFAOYSA-M 2,4,5-triethyl-1-methyl-1-(2-methylhex-4-enyl)-4-phenylpiperidin-1-ium;chloride Chemical compound [Cl-].CCC1C[N+](C)(CC(C)CC=CC)C(CC)CC1(CC)C1=CC=CC=C1 ZRKIAUXZSJNVBA-UHFFFAOYSA-M 0.000 description 1
XMUVFBRSDPZEGB-UHFFFAOYSA-N 2,4,5-trimethyl-1-oct-3-enyl-4-phenylpiperidine Chemical compound C1C(C)N(CCC=CCCCC)CC(C)C1(C)C1=CC=CC=C1 XMUVFBRSDPZEGB-UHFFFAOYSA-N 0.000 description 1
125000006029 2-methyl-2-butenyl 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
ZWJVGUPBCGQOAI-UHFFFAOYSA-N 3-(1,2,5-trimethyl-4-propylpiperidin-1-ium-4-yl)phenol;chloride Chemical compound [Cl-].C=1C=CC(O)=CC=1C1(CCC)CC(C)[NH+](C)CC1C ZWJVGUPBCGQOAI-UHFFFAOYSA-N 0.000 description 1
LWCZTFRHNCQRMR-UHFFFAOYSA-N 3-(1-benzyl-4,5-diethyl-2-methylpiperidin-4-yl)phenol Chemical compound CC1CC(C=2C=C(O)C=CC=2)(CC)C(CC)CN1CC1=CC=CC=C1 LWCZTFRHNCQRMR-UHFFFAOYSA-N 0.000 description 1
UJPWJLVHDYBHTA-UHFFFAOYSA-N 3-(5-butyl-2-ethyl-1-hexyl-4-propylpiperidin-4-yl)phenol Chemical compound C1C(CC)N(CCCCCC)CC(CCCC)C1(CCC)C1=CC=CC(O)=C1 UJPWJLVHDYBHTA-UHFFFAOYSA-N 0.000 description 1
LZKHPQPASHRESU-UHFFFAOYSA-N 3-[1-(cyclohexylmethyl)-2-ethyl-4,5-dipentylpiperidin-4-yl]phenol Chemical compound CCC1CC(C=2C=C(O)C=CC=2)(CCCCC)C(CCCCC)CN1CC1CCCCC1 LZKHPQPASHRESU-UHFFFAOYSA-N 0.000 description 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
NPJIKVNWXSPABG-UHFFFAOYSA-N 3-ethyl-1,4-dimethyl-4-phenyl-2,3-dihydropyridine Chemical compound CCC1CN(C)C=CC1(C)C1=CC=CC=C1 NPJIKVNWXSPABG-UHFFFAOYSA-N 0.000 description 1
OMXNUAXLVIGFQN-UHFFFAOYSA-M 4,5-diethyl-1,1,2-trimethyl-4-phenylpiperidin-1-ium;bromide Chemical compound [Br-].CCC1C[N+](C)(C)C(C)CC1(CC)C1=CC=CC=C1 OMXNUAXLVIGFQN-UHFFFAOYSA-M 0.000 description 1
IAQVXEUPYAYWKP-UHFFFAOYSA-N 4,5-diethyl-1-hex-5-enyl-4-(3-methoxyphenyl)-2-methylpiperidine Chemical compound CCC1CN(CCCCC=C)C(C)CC1(CC)C1=CC=CC(OC)=C1 IAQVXEUPYAYWKP-UHFFFAOYSA-N 0.000 description 1
IZNRPPAJKHBCAC-UHFFFAOYSA-N 4,5-dimethyl-4-phenyl-2-propylpiperidine Chemical compound CC1CNC(CCC)CC1(C)C1=CC=CC=C1 IZNRPPAJKHBCAC-UHFFFAOYSA-N 0.000 description 1
AMVZLYHUKOCBBR-UHFFFAOYSA-N 4-(2-methoxyphenyl)-1,3,4-trimethylpiperidine Chemical compound COC1=CC=CC=C1C1(C)C(C)CN(C)CC1 AMVZLYHUKOCBBR-UHFFFAOYSA-N 0.000 description 1
KFANEUPOIDZDBG-UHFFFAOYSA-N 4-(3-methoxyphenyl)-1,3,4-trimethylpiperidine Chemical compound COC1=CC=CC(C2(C)C(CN(C)CC2)C)=C1 KFANEUPOIDZDBG-UHFFFAOYSA-N 0.000 description 1
IPCICFUATLKXSO-UHFFFAOYSA-N 4-(3-methoxyphenyl)-1,3-dimethyl-4-propylpiperidine Chemical compound C=1C=CC(OC)=CC=1C1(CCC)CCN(C)CC1C IPCICFUATLKXSO-UHFFFAOYSA-N 0.000 description 1
OIVACAORMMAPDU-UHFFFAOYSA-N 4-(3-methoxyphenyl)-3-methyl-1,4-dipropyl-2,3-dihydropyridine Chemical compound C1=CN(CCC)CC(C)C1(CCC)C1=CC=CC(OC)=C1 OIVACAORMMAPDU-UHFFFAOYSA-N 0.000 description 1
125000006043 5-hexenyl group Chemical group 0.000 description 1
BTZNWKCNDBNWIM-UHFFFAOYSA-N 5-iodopent-2-ene Chemical compound CC=CCCI BTZNWKCNDBNWIM-UHFFFAOYSA-N 0.000 description 1
FDKRWZJDFCVMQQ-UHFFFAOYSA-N 6-[2-aminoethyl(ethyl)amino]-2,3-dihydrophthalazine-1,4-dione Chemical compound O=C1NNC(=O)C=2C1=CC(N(CCN)CC)=CC=2 FDKRWZJDFCVMQQ-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
NTZRDKVFLPLTPU-UHFFFAOYSA-N CC[Na] Chemical compound CC[Na] NTZRDKVFLPLTPU-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
230000036592 analgesia Effects 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
235000011132 calcium sulphate Nutrition 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
ZVTQWXCKQTUVPY-UHFFFAOYSA-N chloromethylcyclopropane Chemical compound ClCC1CC1 ZVTQWXCKQTUVPY-UHFFFAOYSA-N 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000012669 compression test Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000017858 demethylation Effects 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
238000007429 general method Methods 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
239000008101 lactose Substances 0.000 description 1
CCZVEWRRAVASGL-UHFFFAOYSA-N lithium;2-methanidylpropane Chemical compound [Li+].CC(C)[CH2-] CCZVEWRRAVASGL-UHFFFAOYSA-N 0.000 description 1
XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 description 1
238000011068 loading method Methods 0.000 description 1
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
239000003887 narcotic antagonist Substances 0.000 description 1
230000003533 narcotic effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000012048 reactive intermediate Substances 0.000 description 1
238000009938 salting Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 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
239000005720 sucrose Substances 0.000 description 1
QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
- 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
- C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

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)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)

DD79217246A 1978-11-29 1979-11-29 Verfahren zur herstellung von 1,2,4,5-tetra-alkyl-4-aryl-piperidinen DD147537A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/965,137 US4284635A (en)	1978-11-29	1978-11-29	Analgesic 1,2,4,5-tetra-alkyl-4-arylpiperidines

Publications (1)

Publication Number	Publication Date
DD147537A5 true DD147537A5 (de)	1981-04-08

Family

ID=25509504

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79217246A DD147537A5 (de)	1978-11-29	1979-11-29	Verfahren zur herstellung von 1,2,4,5-tetra-alkyl-4-aryl-piperidinen

Country Status (26)

Country	Link
US (1)	US4284635A (it)
EP (1)	EP0013078A3 (it)
JP (1)	JPS5573657A (it)
KR (1)	KR830001214A (it)
AR (1)	AR224138A1 (it)
AT (1)	ATA750879A (it)
AU (1)	AU529136B2 (it)
BE (1)	BE880220A (it)
CA (1)	CA1121357A (it)
DD (1)	DD147537A5 (it)
DK (1)	DK504979A (it)
EG (1)	EG14137A (it)
ES (2)	ES486425A0 (it)
FI (1)	FI793663A7 (it)
FR (2)	FR2442836A1 (it)
GB (1)	GB2038812B (it)
GR (1)	GR72292B (it)
HU (1)	HU178532B (it)
IL (1)	IL58793A0 (it)
IT (1)	IT1126406B (it)
LU (1)	LU81923A1 (it)
PH (1)	PH15420A (it)
PL (1)	PL123672B1 (it)
PT (1)	PT70486A (it)
SU (1)	SU967275A3 (it)
ZA (1)	ZA796336B (it)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5212183A (en) *	1981-11-14	1993-05-18	Basf Aktiengesellschaft	4-(p-tert.-butylphenyl)-3-methylpiperidines substituted at the nitrogen, their quaternary salts and their use as fungicides
US4485109A (en) *	1982-05-07	1984-11-27	E. I. Du Pont De Nemours And Company	4-Aryl-4-piperidinecarbinols
US4581456A (en) *	1983-09-21	1986-04-08	Eli Lilly And Company	Processes for preparing picenadol precursors and novel intermediates thereof
ZW10287A1 (en) *	1986-07-15	1988-01-13	Hoffmann La Roche	Tetrahydronaphthaline and indane derivatives
EP0299549A3 (en) *	1987-07-09	1989-02-08	Duphar International Research B.V	Tertiary 2,5-dialkyl-3-phenyl-piperidine derivatives having opiate-antagonistic activity
CA1337418C (en) *	1988-03-28	1995-10-24	Engelbert Ciganek	4-aryl-4-piperiding (or pyrrolidine or hexahydroazepine) carbinols and heterocyclic analogs thereof
US5136040A (en) *	1991-02-26	1992-08-04	Eli Lilly And Company	Preparation of substituted tetrahydropyridines
US5159081A (en) *	1991-03-29	1992-10-27	Eli Lilly And Company	Intermediates of peripherally selective n-carbonyl-3,4,4-trisubstituted piperidine opioid antagonists
US5270328A (en) *	1991-03-29	1993-12-14	Eli Lilly And Company	Peripherally selective piperidine opioid antagonists
US5250542A (en) *	1991-03-29	1993-10-05	Eli Lilly And Company	Peripherally selective piperidine carboxylate opioid antagonists
GB9912410D0 (en)	1999-05-28	1999-07-28	Pfizer Ltd	Compounds useful in therapy
GB9912415D0 (en)	1999-05-28	1999-07-28	Pfizer Ltd	Compounds useful in therapy
GB9912413D0 (en)	1999-05-28	1999-07-28	Pfizer Ltd	Compounds useful in therapy
GB9912417D0 (en)	1999-05-28	1999-07-28	Pfizer Ltd	Compounds useful in therapy
GB9912416D0 (en) *	1999-05-28	1999-07-28	Pfizer Ltd	Compounds useful in therapy
GB9912411D0 (en)	1999-05-28	1999-07-28	Pfizer Ltd	Compounds useful in therapy

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2892842A (en) *		1959-06-30		Their preparation
US2956058A (en) *	1957-08-19	1960-10-11	Lilly Co Eli	Novel substituted piperidines and pyrrolidines
US3043845A (en) *	1958-12-29	1962-07-10	Abbott Lab	Phenylmethylpiperidine derivatives
US3080372A (en) *	1960-03-25	1963-03-05	Res Lab Dr C Janssen	1-aroylalkyl-4-arylpiperidine derivatives
NL123743C (it) *	1963-09-18
US3574219A (en) *	1967-09-27	1971-04-06	Tanabe Seiyaku Co	1-(beta-hydroxyphenethyl)-2,3-dimethyl-3-(3-hydroxyphenyl)-piperidine
US3936468A (en) *	1969-10-27	1976-02-03	Sumitomo Chemical Company, Ltd.	Phenylbutanol derivatives
GB1403942A (en) *	1973-04-05	1975-08-28	Ciba Geigy Ag	Piperidine derivatives
AR206937A1 (es) *	1974-09-06	1976-08-31	Lilly Co Eli	Procedimiento para preparar compuestos de 1-sustituido-4-alquil-4-fenil-piperidina
US4115400A (en) *	1976-05-27	1978-09-19	Eli Lilly And Company	1-Azoniabicyclo[3.1.0]hexanes
ZA777356B (en) *	1976-12-17	1979-01-31	Rohm & Haas	Arthropod repellents

1978
- 1978-11-29 US US05/965,137 patent/US4284635A/en not_active Expired - Lifetime
1979
- 1979-11-22 EP EP79302674A patent/EP0013078A3/en not_active Ceased
- 1979-11-22 CA CA000340379A patent/CA1121357A/en not_active Expired
- 1979-11-22 AU AU53100/79A patent/AU529136B2/en not_active Expired - Fee Related
- 1979-11-22 PT PT70486A patent/PT70486A/pt unknown
- 1979-11-22 FI FI793663A patent/FI793663A7/fi not_active Application Discontinuation
- 1979-11-22 GB GB7940422A patent/GB2038812B/en not_active Expired
- 1979-11-22 ZA ZA00796336A patent/ZA796336B/xx unknown
- 1979-11-23 BE BE1/9621A patent/BE880220A/fr unknown
- 1979-11-23 IL IL58793A patent/IL58793A0/xx unknown
- 1979-11-23 FR FR7928977A patent/FR2442836A1/fr active Granted
- 1979-11-23 PH PH23322A patent/PH15420A/en unknown
- 1979-11-26 LU LU81923A patent/LU81923A1/fr unknown
- 1979-11-26 JP JP15349279A patent/JPS5573657A/ja active Pending
- 1979-11-26 PL PL1979219885A patent/PL123672B1/pl unknown
- 1979-11-27 HU HU79EI892A patent/HU178532B/hu unknown
- 1979-11-27 AR AR279039A patent/AR224138A1/es active
- 1979-11-27 GR GR60608A patent/GR72292B/el unknown
- 1979-11-27 EG EG708/79A patent/EG14137A/xx active
- 1979-11-27 AT AT0750879A patent/ATA750879A/de not_active Application Discontinuation
- 1979-11-27 IT IT27614/79A patent/IT1126406B/it active
- 1979-11-28 ES ES486425A patent/ES486425A0/es active Granted
- 1979-11-28 SU SU792847573A patent/SU967275A3/ru active
- 1979-11-28 DK DK504979A patent/DK504979A/da unknown
- 1979-11-28 KR KR1019790004179A patent/KR830001214A/ko active Pending
- 1979-11-29 DD DD79217246A patent/DD147537A5/de unknown
1980
- 1980-05-13 FR FR8010755A patent/FR2453154A1/fr active Granted
- 1980-07-31 ES ES493915A patent/ES493915A0/es active Granted

Also Published As

Publication number	Publication date
PL123672B1 (en)	1982-11-30
LU81923A1 (fr)	1980-04-22
SU967275A3 (ru)	1982-10-15
ES8200664A1 (es)	1981-11-16
IT1126406B (it)	1986-05-21
GR72292B (it)	1983-10-17
DK504979A (da)	1980-05-30
AU5310079A (en)	1980-05-29
EP0013078A2 (en)	1980-07-09
KR830001214A (ko)	1983-04-29
ES8101551A1 (es)	1980-12-16
ES486425A0 (es)	1980-12-16
FI793663A7 (fi)	1980-05-30
JPS5573657A (en)	1980-06-03
ATA750879A (de)	1983-03-15
CA1121357A (en)	1982-04-06
PH15420A (en)	1983-01-07
EG14137A (en)	1983-09-30
BE880220A (fr)	1980-05-23
AU529136B2 (en)	1983-05-26
IT7927614A0 (it)	1979-11-27
AR224138A1 (es)	1981-10-30
GB2038812B (en)	1983-01-06
ES493915A0 (es)	1981-11-16
EP0013078A3 (en)	1980-10-01
US4284635A (en)	1981-08-18
FR2442836A1 (fr)	1980-06-27
ZA796336B (en)	1981-06-24
GB2038812A (en)	1980-07-30
FR2453154B1 (it)	1983-05-27
PL219885A1 (it)	1980-12-01
IL58793A0 (en)	1980-02-29
PT70486A (en)	1979-12-01
HU178532B (en)	1982-05-28
FR2442836B1 (it)	1983-07-29
FR2453154A1 (fr)	1980-10-31

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DE29724281U1 (de)	2000-08-10	4-Phenylpiperidin-Verbindungen
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CH625787A5 (it)	1981-10-15
DE2952213A1 (de)	1980-07-24	Phenoxyphenylpiperidine
DE2002840A1 (de)	1970-08-06	2,3,5-trisubstit,-2'-Hydroxy-6,7-benzomorphane und Verfahren zu deren Herstellung
DE2657978C3 (de)	1981-02-12	Linksdrehende Enantiomere und Racemate von Trifluormethylthio(und -sulfonyl)cyproheptadinderivaten, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
DE2407115A1 (de)	1974-10-10	Neue 1,4-dihydropyridinderivate
DE3125471A1 (de)	1982-03-18	"piperazinderivate, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten"
DE2719211C3 (de)	1982-01-07	1-(2-Phenylamino-äthyl)-4-(N-phenyl-N-propionylamino)-piperidine, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
DE2524054A1 (de)	1975-12-18	1-cycloalkylmethyl-3a-(substituiertes-phenyl)-decahydroisochinoline
DE2628570B2 (it)	1980-02-07
DE2524053A1 (de)	1975-12-18	1-aethyl-3a-substituiertes-phenyl- decahydroisochinoline
DE2724478C2 (de)	1986-05-22	5,11-Dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-on-derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DD141156A5 (de)	1980-04-16	Verfahren zur herstellung von 4a-aryl-octahydro-1h-2-pyrindinen
EP0389425B1 (de)	1995-04-26	Neue Benzothiopyranylamine
DE2748466A1 (de)	1978-05-03	4a-aryloctahydro-1h-2-pyrindine
DE2425767A1 (de)	1975-01-09	3-alkyl-9-aminoalkyl-1,2,3,4-tetrahydrocarbazole und ihre verwendung in arzneimitteln
DE3028064C2 (it)	1989-11-09
DE2657950A1 (de)	1977-06-30	Trifluormethylthioderivate von cyproheptadin
DE2528194C2 (de)	1982-10-14	Benzhydryloxyäthylamin-Derivate, deren Salze, Verfahren zur Herstellung derselben und solche enthaltende Arzneimittel
DE2912026C2 (it)	1990-04-05
EP0013424B1 (de)	1982-11-17	Spiro(dibenz(b,f)thiepin-piperidine), Zwischenprodukte zu ihrer Herstellung und sie enthaltende Arzneimittel
US4228288A (en)	1980-10-14	Certain substituted 3,4,5,6-tetrahydropyridinium salt intermediates
DD148720A5 (de)	1981-06-10	Verfahren zur herstellung von 4-amino-2-piperidinochinazolin-derivaten