BG61319B2 - Метод за получаване на арилпиперидинкарбиноли - Google Patents
Метод за получаване на арилпиперидинкарбиноли Download PDFInfo
- Publication number
- BG61319B2 BG61319B2 BG098349A BG9834993A BG61319B2 BG 61319 B2 BG61319 B2 BG 61319B2 BG 098349 A BG098349 A BG 098349A BG 9834993 A BG9834993 A BG 9834993A BG 61319 B2 BG61319 B2 BG 61319B2
- Authority
- BG
- Bulgaria
- Prior art keywords
- formula
- compound
- alkyl
- trans
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- -1 trifluoralkyl Chemical group 0.000 claims abstract description 12
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims abstract description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 9
- VLLPYAIUEKEIRQ-AAEUAGOBSA-N ethyl (3s,4r)-4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylate Chemical compound C1C(=O)N(C)C(=O)[C@@H](C(=O)OCC)[C@@H]1C1=CC=C(F)C=C1 VLLPYAIUEKEIRQ-AAEUAGOBSA-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 5
- 239000002904 solvent Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 229910052987 metal hydride Inorganic materials 0.000 claims description 3
- 150000004681 metal hydrides Chemical class 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- TWTXBOKSRNPUQL-JQWIXIFHSA-N ethyl (3s,4r)-4-(4-fluorophenyl)-2,6-dioxopiperidine-3-carboxylate Chemical compound C1C(=O)NC(=O)[C@@H](C(=O)OCC)[C@@H]1C1=CC=C(F)C=C1 TWTXBOKSRNPUQL-JQWIXIFHSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims description 2
- LVERLLNWOIPJSH-ONGXEEELSA-N COC(=O)[C@@H]1C(NC(C[C@H]1C1=CC=C(C=C1)F)=O)=O Chemical compound COC(=O)[C@@H]1C(NC(C[C@H]1C1=CC=C(C=C1)F)=O)=O LVERLLNWOIPJSH-ONGXEEELSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- CXRHUYYZISIIMT-AAEUAGOBSA-N [(3s,4r)-4-(4-fluorophenyl)-1-methylpiperidin-3-yl]methanol Chemical compound OC[C@@H]1CN(C)CC[C@H]1C1=CC=C(F)C=C1 CXRHUYYZISIIMT-AAEUAGOBSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 125000004494 ethyl ester group Chemical group 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
- 239000000047 product Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- HJJPJSXJAXAIPN-UHFFFAOYSA-N arecoline Chemical compound COC(=O)C1=CCCN(C)C1 HJJPJSXJAXAIPN-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 2
- NTOIKDYVJIWVSU-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)C(O)(C(O)=O)C(O)(C(O)=O)C(=O)C1=CC=C(C)C=C1 NTOIKDYVJIWVSU-UHFFFAOYSA-N 0.000 description 2
- MXAMATMCPUOCEA-UHFFFAOYSA-N 4-(4-fluorophenyl)piperidine-2,6-dione Chemical compound C1=CC(F)=CC=C1C1CC(=O)NC(=O)C1 MXAMATMCPUOCEA-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 229960002296 paroxetine Drugs 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- KBEBGUQPQBELIU-CMDGGOBGSA-N Ethyl cinnamate Chemical compound CCOC(=O)\C=C\C1=CC=CC=C1 KBEBGUQPQBELIU-CMDGGOBGSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- IBOPBHBOBJYXTD-JQWIXIFHSA-N [(3s,4r)-4-(4-fluorophenyl)piperidin-3-yl]methanol Chemical compound OC[C@@H]1CNCC[C@H]1C1=CC=C(F)C=C1 IBOPBHBOBJYXTD-JQWIXIFHSA-N 0.000 description 1
- NJVHJTQSGGRHGP-UHFFFAOYSA-K [Li].[Al+3].[Cl-].[Cl-].[Cl-] Chemical compound [Li].[Al+3].[Cl-].[Cl-].[Cl-] NJVHJTQSGGRHGP-UHFFFAOYSA-K 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- KBEBGUQPQBELIU-UHFFFAOYSA-N cinnamic acid ethyl ester Natural products CCOC(=O)C=CC1=CC=CC=C1 KBEBGUQPQBELIU-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000020176 deacylation Effects 0.000 description 1
- 238000005947 deacylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- UNAXNPTZJKKUGO-UHFFFAOYSA-N ethyl 3-(4-fluorophenyl)prop-2-enoate Chemical compound CCOC(=O)C=CC1=CC=C(F)C=C1 UNAXNPTZJKKUGO-UHFFFAOYSA-N 0.000 description 1
- TWTXBOKSRNPUQL-UHFFFAOYSA-N ethyl 4-(4-fluorophenyl)-2,6-dioxopiperidine-3-carboxylate Chemical compound C1C(=O)NC(=O)C(C(=O)OCC)C1C1=CC=C(F)C=C1 TWTXBOKSRNPUQL-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- LEWPSSCATGWXEP-UHFFFAOYSA-M sodium;1,3-benzodioxol-5-olate Chemical compound [Na+].[O-]C1=CC=C2OCOC2=C1 LEWPSSCATGWXEP-UHFFFAOYSA-M 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 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
- C07D211/80—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 two double bonds between ring members or between ring members and non-ring members
- C07D211/84—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 two 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 directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
- C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB858520153A GB8520153D0 (en) | 1985-08-10 | 1985-08-10 | Chemical process |
| GB868612579A GB8612579D0 (en) | 1986-05-23 | 1986-05-23 | Chemical process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BG61319B2 true BG61319B2 (bg) | 1997-05-30 |
Family
ID=26289644
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG098349A BG61319B2 (bg) | 1985-08-10 | 1993-12-29 | Метод за получаване на арилпиперидинкарбиноли |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4902801A (fr) |
| EP (1) | EP0223334B1 (fr) |
| JP (2) | JPH0696551B2 (fr) |
| AU (1) | AU582456B2 (fr) |
| BG (1) | BG61319B2 (fr) |
| CA (1) | CA1310649C (fr) |
| CY (1) | CY1708A (fr) |
| DE (1) | DE3680184D1 (fr) |
| DK (1) | DK169730B1 (fr) |
| ES (2) | ES2000603A6 (fr) |
| GR (1) | GR862102B (fr) |
| HK (1) | HK69793A (fr) |
| IE (1) | IE58831B1 (fr) |
| MX (1) | MX171822B (fr) |
| NZ (1) | NZ217141A (fr) |
| PT (1) | PT83179B (fr) |
| SG (1) | SG27793G (fr) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8714707D0 (en) * | 1987-06-23 | 1987-07-29 | Beecham Group Plc | Chemical process |
| DK588289D0 (da) * | 1989-11-22 | 1989-11-22 | Ferrosan As | Ny heterocyklisk kemi |
| JPH04288059A (ja) * | 1991-03-14 | 1992-10-13 | Nippon Paint Co Ltd | 複素環化合物及びその製造法 |
| GB9209687D0 (en) * | 1992-05-06 | 1992-06-17 | Smithkline Beecham Plc | Novel process |
| US5258517A (en) * | 1992-08-06 | 1993-11-02 | Sepracor, Inc. | Method of preparing optically pure precursors of paroxetine |
| GB9305175D0 (en) * | 1993-03-13 | 1993-04-28 | Smithkline Beecham Plc | Novel process |
| GB9325644D0 (en) * | 1993-12-15 | 1994-02-16 | Smithkline Beecham Plc | Novel formulation |
| EP0789573A4 (fr) * | 1995-08-03 | 1998-04-29 | Fmc Corp | Reductions au moyen d'hydrures |
| US6444190B2 (en) | 1995-08-03 | 2002-09-03 | Fmc Corporation | Reduction compositions and processes for making the same |
| ES2121685B1 (es) * | 1996-04-10 | 1999-09-16 | Vita Invest Sa | Procedimiento para la obtencion de (+)-trans-4(4-fluoro-fenil)-3-hidroximetil-1-metilpiperidina. |
| JP3446468B2 (ja) | 1996-04-15 | 2003-09-16 | 旭硝子株式会社 | ピペリジンカルビノール類の製造方法 |
| US5936090A (en) * | 1996-05-24 | 1999-08-10 | Fmc Corporation | Processes for the reduction of imide ester functionality |
| EP1384720A1 (fr) | 1996-06-13 | 2004-01-28 | SUMIKA FINE CHEMICALS Co., Ltd. | Procédé de séchage pour le chlorhydrate de paroxetine |
| US6638948B1 (en) | 1996-09-09 | 2003-10-28 | Pentech Pharmaceuticals, Inc. | Amorphous paroxetine composition |
| WO1998013319A1 (fr) * | 1996-09-24 | 1998-04-02 | Fmc Corporation | Nouvelles compositions de reduction et leurs procedes de fabrication |
| GB9623359D0 (en) * | 1996-11-09 | 1997-01-08 | Smithkline Beecham Plc | Novel process |
| EP0975595B9 (fr) * | 1997-04-07 | 2009-09-16 | Georgetown University | Analogues de cocaine |
| GB9710004D0 (en) * | 1997-05-17 | 1997-07-09 | Knoll Ag | Chemical process |
| HUP0003958A3 (en) * | 1997-05-29 | 2001-06-28 | Smithkline Beecham Plc | Process for preparation of 4-aryl-piperidines and intermediates |
| SI0994872T1 (fr) | 1997-06-10 | 2001-08-31 | Synthon Bv | |
| DE69910691T2 (de) * | 1998-06-29 | 2004-07-08 | Sumika Fine Chemical Co. Ltd. | L-Tartrate von Trans-(-)-4-(4-Fluorphenyl)-3-Hydroxymethyl-Piperidin Verbindungen und Verfahren zu ihrer Herstellung |
| CH689805A8 (fr) * | 1998-07-02 | 2000-02-29 | Smithkline Beecham Plc | Méthanesulfonate de paroxétine, procédé pour sa préparation et compositions pharmaceutiques le contenant. |
| WO2000026187A1 (fr) * | 1998-11-02 | 2000-05-11 | Synthon B.V. | Procede de production de 4-arylpiperidine-3-carbinols et composes correspondants |
| GB9915303D0 (en) * | 1999-06-30 | 1999-09-01 | Smithkline Beecham Plc | Novel process |
| IT1313702B1 (it) | 1999-08-02 | 2002-09-09 | Chemi Spa | Processo per la preparazione di derivati 3-sostituiti di 4-fenil-piperidine. |
| GB9920147D0 (en) * | 1999-08-25 | 1999-10-27 | Smithkline Beecham Plc | Novel process |
| GB9924855D0 (en) * | 1999-10-20 | 1999-12-22 | Smithkline Beecham Plc | Novel processes |
| AU1037701A (en) * | 1999-10-20 | 2001-04-30 | Smithkline Beecham Plc | Process for the preparation of 4-(fluorophenyl)piperidine esters |
| GB9924882D0 (en) * | 1999-10-20 | 1999-12-22 | Smithkline Beecham Plc | Novel process |
| GB9930577D0 (en) * | 1999-12-23 | 2000-02-16 | Smithkline Beecham Plc | Novel process |
| CZ20023694A3 (cs) | 2000-05-12 | 2003-05-14 | Synthon B. V. | Tosylátové soli 4-(p-fluorfenyl)-piperidin-3-methanolů |
| US6833458B2 (en) | 2000-06-05 | 2004-12-21 | Development Center For Biotechnology | Practical syntheses of chiral trans-3, 4-disubstituted piperidines and the intermediates |
| WO2002028834A1 (fr) * | 2000-10-06 | 2002-04-11 | Smithkline Beecham P.L.C. | Procede de preparation de carbonols d'aryl-piperidine et produits intermediaires de ces derniers |
| KR20030067742A (ko) * | 2001-01-04 | 2003-08-14 | 페레르 인터내쇼날 에스.에이. | (±)트랜스-4-ｐ-플루오로페닐-3-하이드록시메틸-1-메틸피페리딘의 제조 과정 |
| US6777554B2 (en) | 2001-02-05 | 2004-08-17 | Teva Pharmaceutical Industries Ltd. | Preparation of N-methylparoxetine and related intermediate compounds |
| CA2438892A1 (fr) * | 2001-02-24 | 2002-09-06 | Spurcourt Limited | Procede de preparation de la paroxetine et intermediaires a cet usage |
| US6930186B2 (en) | 2001-06-13 | 2005-08-16 | Teva Pharmacetical Industries Ltd. | Process for the preparation of paroxetine substantially free of alkoxy impurities |
| KR100477048B1 (ko) * | 2002-07-05 | 2005-03-17 | 임광민 | 피페리딘 화합물의 새로운 제조방법 |
| WO2004043921A1 (fr) * | 2002-11-11 | 2004-05-27 | Natco Pharma Limited | Nouveau procede de preparation de 4-aryl-3-hydroxymethyl-1-methylpiperidines |
| US20050266082A1 (en) * | 2004-05-26 | 2005-12-01 | Patel Satishkumar A | Preparation of stable paroxetine HC1 ER tablets using a melt granulation process |
| CN101205211B (zh) * | 2006-12-19 | 2011-12-14 | 北京德众万全药物技术开发有限公司 | 一种盐酸帕罗西汀重要中间体的制备方法 |
| IN2013MU03596A (fr) * | 2013-11-18 | 2015-07-24 | Piramal Entpr Ltd | |
| CN104262255A (zh) * | 2014-09-22 | 2015-01-07 | 四川大学 | 一种不对称催化合成γ-硝基吡唑酰胺化合物的方法 |
| CN104402800A (zh) * | 2014-12-02 | 2015-03-11 | 千辉药业（安徽）有限责任公司 | 一种反式-4-(4-氟苯基)-3-羟甲基-1-甲基哌啶的制备方法 |
| WO2022269643A1 (fr) * | 2021-06-25 | 2022-12-29 | Vihita Chem Private Limited | Procédé amélioré pour la préparation d'un intermédiaire pour la paroxétine |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE625656A (fr) * | 1961-12-05 | |||
| NL125654C (fr) * | 1963-12-17 | 1900-01-01 | ||
| US3666746A (en) * | 1969-06-25 | 1972-05-30 | Gaf Corp | Pyrrolidonylphenyl azo dyestuffs |
| US3681327A (en) * | 1970-07-01 | 1972-08-01 | Exxon Research Engineering Co | N-methylenethiophosphate derivatives of 1,3-thiazines and 1,4-thiazanes |
| GB1422263A (en) * | 1973-01-30 | 1976-01-21 | Ferrosan As | 4-phenyl-piperidine compounds |
| US3947460A (en) * | 1974-06-27 | 1976-03-30 | Sandoz, Inc. | 5-Hydroxy-5-substituted phenyl-pyrrolidones and piperidinones |
| EP0047516B1 (fr) * | 1980-09-04 | 1984-01-04 | Toray Industries, Inc. | Dérivés de la propylamine et leur procédé de préparation |
| US4585777A (en) * | 1984-02-07 | 1986-04-29 | A/S Ferrosan | (-)-Trans-4-(4-fluorophenyl)-3-(4-methoxyphenoxy)methylpiperidine for potentiating 5-HT |
-
1986
- 1986-08-06 DE DE8686306070T patent/DE3680184D1/de not_active Expired - Lifetime
- 1986-08-06 EP EP19860306070 patent/EP0223334B1/fr not_active Expired - Lifetime
- 1986-08-08 JP JP61185429A patent/JPH0696551B2/ja not_active Expired - Lifetime
- 1986-08-08 ES ES8600960A patent/ES2000603A6/es not_active Expired
- 1986-08-08 MX MX006890A patent/MX171822B/es unknown
- 1986-08-08 US US06/894,695 patent/US4902801A/en not_active Expired - Lifetime
- 1986-08-08 CA CA000515598A patent/CA1310649C/fr not_active Expired - Lifetime
- 1986-08-08 GR GR862102A patent/GR862102B/el unknown
- 1986-08-08 NZ NZ217141A patent/NZ217141A/xx unknown
- 1986-08-08 PT PT83179A patent/PT83179B/pt unknown
- 1986-08-08 DK DK380986A patent/DK169730B1/da not_active IP Right Cessation
- 1986-08-08 IE IE213586A patent/IE58831B1/en not_active IP Right Cessation
- 1986-08-08 AU AU61012/86A patent/AU582456B2/en not_active Expired
-
1987
- 1987-12-30 ES ES8703767A patent/ES2005745A6/es not_active Expired
-
1993
- 1993-03-15 SG SG277/93A patent/SG27793G/en unknown
- 1993-07-22 HK HK697/93A patent/HK69793A/xx not_active IP Right Cessation
- 1993-12-29 BG BG098349A patent/BG61319B2/bg unknown
-
1994
- 1994-01-14 CY CY170894A patent/CY1708A/xx unknown
- 1994-05-25 JP JP6133871A patent/JPH08809B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| SG27793G (en) | 1993-05-21 |
| IE58831B1 (en) | 1993-11-17 |
| DK380986D0 (da) | 1986-08-08 |
| MX171822B (es) | 1993-11-17 |
| CA1310649C (fr) | 1992-11-24 |
| DE3680184D1 (de) | 1991-08-14 |
| AU582456B2 (en) | 1989-03-23 |
| CY1708A (en) | 1994-01-14 |
| DK380986A (da) | 1987-02-11 |
| JPS6239566A (ja) | 1987-02-20 |
| ES2005745A6 (es) | 1989-03-16 |
| AU6101286A (en) | 1987-02-12 |
| JPH0696551B2 (ja) | 1994-11-30 |
| JPH07138228A (ja) | 1995-05-30 |
| IE862135L (en) | 1987-02-10 |
| PT83179A (en) | 1986-09-01 |
| GR862102B (en) | 1986-12-30 |
| ES2000603A6 (es) | 1988-03-01 |
| EP0223334B1 (fr) | 1991-07-10 |
| US4902801A (en) | 1990-02-20 |
| PT83179B (pt) | 1989-03-30 |
| DK169730B1 (da) | 1995-01-30 |
| NZ217141A (en) | 1989-06-28 |
| JPH08809B2 (ja) | 1996-01-10 |
| HK69793A (en) | 1993-07-30 |
| EP0223334A1 (fr) | 1987-05-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BG61319B2 (bg) | Метод за получаване на арилпиперидинкарбиноли | |
| US4243807A (en) | 4-Phenoxymethyl-piperidines | |
| US4861893A (en) | Chemical process | |
| US5039803A (en) | Process for preparing aryl-substituted piperidines | |
| NO160514B (no) | Analogifremgangsm te for fremstilling av farmasoeytisk aktive pyrimid-2-on-derivater. | |
| US5869661A (en) | Method of producing a quinolonecarboxylic acid derivative | |
| NO166712B (no) | Fremgangsmaate ved fremstilling av pyrrolidonderivater. | |
| DK173902B1 (da) | Fremgangsmåde til fremstilling af paroxetin eller et farmaceutisk acceptabelt salt deraf | |
| FI87561B (fi) | Foerfarande foer framstaellning av fenylpiperidinkarbinoler samt i foerfarandet anvaendbara nya mellanprodukter | |
| CA1327585C (fr) | Procede pour la preparation d'arylpiperidinediones | |
| JPS6355512B2 (fr) | ||
| US6350902B2 (en) | Process for the selective N-formylation of N-hydroxylamines | |
| EP0236754B1 (fr) | Procédé pour la préparation de composés acétyl-4-isoquinoléiniques | |
| NO174294B (no) | Fremgangsmaate og mellomprodukter for fremstilling av piperidin- karbinoler | |
| EP0502024B1 (fr) | Intermediaires de 4-heteroaryle piperidine et leur preparation | |
| US4254279A (en) | Ester resolution process | |
| KR800001048B1 (ko) | 4-할로 메틸-2-피롤리디논의 제조방법 | |
| JPH08319265A (ja) | Ｎ−メチル−メトキシイミノ酢酸アミド誘導体の製造法およびその中間体 | |
| JPH07224033A (ja) | 光学活性アザスピロ化合物の製法 | |
| IE63293B1 (en) | New process for separating optical isomers of 1,4-dihydropyridine derivatives | |
| NO790342L (no) | Fremgangsmaate for fremstilling av alkyl-2-arylakrylater | |
| JPH0525878B2 (fr) | ||
| NO152132B (no) | Fremgangsmaate til fremstilling av karbazolderivater |