DD144545A5 - Verfahren zur herstellung von neuen tetrahydropyridin-und piperidinderivaten - Google Patents

Verfahren zur herstellung von neuen tetrahydropyridin-und piperidinderivaten Download PDF

Info

Publication number: DD144545A5
Authority: DD; German Democratic Republic
Prior art keywords: hydrogen; general formula; radical; further substituted; ring
Prior art date: 1978-06-22

Application number

DD79213724A

Other languages

German (de)

English (en)

Inventor

Romeo Paioni

Walter Schilling

Raymond Bernasconi

Original Assignee

Ciba Geigy Ag

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.)

1978-06-22

Filing date

1979-06-19

Publication date

1980-10-22

1979-06-19 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1980-10-22 Publication of DD144545A5 publication Critical patent/DD144545A5/de

Links

NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title claims description 36
VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 title claims description 6
238000004519 manufacturing process Methods 0.000 title description 4
-1 4-piperidyl Chemical group 0.000 claims description 139
150000001875 compounds Chemical class 0.000 claims description 125
239000002253 acid Substances 0.000 claims description 74
239000001257 hydrogen Substances 0.000 claims description 59
229910052739 hydrogen Inorganic materials 0.000 claims description 59
239000000203 mixture Substances 0.000 claims description 46
150000003839 salts Chemical class 0.000 claims description 46
238000000034 method Methods 0.000 claims description 43
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
150000002431 hydrogen Chemical class 0.000 claims description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
229910052736 halogen Inorganic materials 0.000 claims description 21
150000002367 halogens Chemical class 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 20
125000003545 alkoxy group Chemical group 0.000 claims description 19
229910052757 nitrogen Inorganic materials 0.000 claims description 16
238000002360 preparation method Methods 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 15
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
229910052794 bromium Inorganic materials 0.000 claims description 14
239000003795 chemical substances by application Substances 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
239000007795 chemical reaction product Substances 0.000 claims description 12
229910052727 yttrium Inorganic materials 0.000 claims description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
229910052783 alkali metal Inorganic materials 0.000 claims description 11
229910052740 iodine Inorganic materials 0.000 claims description 11
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 9
125000000304 alkynyl group Chemical group 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
150000003053 piperidines Chemical class 0.000 claims description 6
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 6
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 4
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
239000011630 iodine Substances 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 4
239000002184 metal Substances 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 3
230000003287 optical effect Effects 0.000 claims description 3
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
150000001721 carbon Chemical group 0.000 claims 1
239000000243 solution Substances 0.000 description 98
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 94
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 91
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 87
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 84
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 77
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 74
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 61
239000007858 starting material Substances 0.000 description 60
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 51
150000003254 radicals Chemical class 0.000 description 49
238000006243 chemical reaction Methods 0.000 description 46
239000011541 reaction mixture Substances 0.000 description 46
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
239000000725 suspension Substances 0.000 description 29
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
239000013078 crystal Substances 0.000 description 26
239000000155 melt Substances 0.000 description 25
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
239000005457 ice water Substances 0.000 description 22
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 21
239000000706 filtrate Substances 0.000 description 21
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 20
238000009835 boiling Methods 0.000 description 20
239000012074 organic phase Substances 0.000 description 19
239000002904 solvent Substances 0.000 description 19
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 18
229910052938 sodium sulfate Inorganic materials 0.000 description 16
235000011152 sodium sulphate Nutrition 0.000 description 16
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
239000012280 lithium aluminium hydride Substances 0.000 description 15
238000010438 heat treatment Methods 0.000 description 14
239000003054 catalyst Substances 0.000 description 13
238000001816 cooling Methods 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
239000005909 Kieselgur Substances 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
239000002585 base Substances 0.000 description 12
239000012043 crude product Substances 0.000 description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
125000001424 substituent group Chemical group 0.000 description 12
229960000583 acetic acid Drugs 0.000 description 11
230000002378 acidificating effect Effects 0.000 description 11
239000003960 organic solvent Substances 0.000 description 11
238000001953 recrystallisation Methods 0.000 description 11
238000003756 stirring Methods 0.000 description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
150000007513 acids Chemical class 0.000 description 10
239000000284 extract Substances 0.000 description 10
239000002244 precipitate Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
238000007363 ring formation reaction Methods 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000004480 active ingredient Substances 0.000 description 9
238000002425 crystallisation Methods 0.000 description 9
150000002148 esters Chemical class 0.000 description 9
239000003921 oil Substances 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000007864 aqueous solution Substances 0.000 description 8
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 8
230000008025 crystallization Effects 0.000 description 8
239000007868 Raney catalyst Substances 0.000 description 7
229910000564 Raney nickel Inorganic materials 0.000 description 7
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 7
125000005907 alkyl ester group Chemical group 0.000 description 7
244000309464 bull Species 0.000 description 7
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 7
239000012362 glacial acetic acid Substances 0.000 description 7
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
229910000041 hydrogen chloride Inorganic materials 0.000 description 7
239000000463 material Substances 0.000 description 7
230000008018 melting Effects 0.000 description 7
238000002844 melting Methods 0.000 description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
239000000126 substance Substances 0.000 description 7
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
229910052500 inorganic mineral Inorganic materials 0.000 description 6
229910052744 lithium Inorganic materials 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
235000010755 mineral Nutrition 0.000 description 6
239000011707 mineral Substances 0.000 description 6
230000007935 neutral effect Effects 0.000 description 6
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
235000011181 potassium carbonates Nutrition 0.000 description 6
RQFHSVDAFPZYON-UHFFFAOYSA-N 4-(6,7,8,9-tetrahydrodibenzofuran-2-yl)piperidine Chemical compound C1CCCC(C2=C3)=C1OC2=CC=C3C1CCNCC1 RQFHSVDAFPZYON-UHFFFAOYSA-N 0.000 description 5
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 5
239000005695 Ammonium acetate Substances 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
125000003342 alkenyl group Chemical group 0.000 description 5
235000019257 ammonium acetate Nutrition 0.000 description 5
229940043376 ammonium acetate Drugs 0.000 description 5
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 5
239000000935 antidepressant agent Substances 0.000 description 5
229940005513 antidepressants Drugs 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
150000003840 hydrochlorides Chemical class 0.000 description 5
238000007327 hydrogenolysis reaction Methods 0.000 description 5
238000011065 in-situ storage Methods 0.000 description 5
239000012442 inert solvent Substances 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
239000002609 medium Substances 0.000 description 5
150000007524 organic acids Chemical class 0.000 description 5
KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical class O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 description 5
238000000746 purification Methods 0.000 description 5
238000003797 solvolysis reaction Methods 0.000 description 5
239000000829 suppository Substances 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
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 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 4
229910000085 borane Inorganic materials 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
150000001735 carboxylic acids Chemical class 0.000 description 4
239000003638 chemical reducing agent Substances 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
230000018044 dehydration Effects 0.000 description 4
238000006297 dehydration reaction Methods 0.000 description 4
239000003480 eluent Substances 0.000 description 4
125000004494 ethyl ester group Chemical group 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
229920000159 gelatin Polymers 0.000 description 4
235000019322 gelatine Nutrition 0.000 description 4
150000004678 hydrides Chemical class 0.000 description 4
150000002440 hydroxy compounds Chemical class 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000012452 mother liquor Substances 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
239000012071 phase Substances 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical class O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000012429 reaction media Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
239000000454 talc Substances 0.000 description 4
229910052623 talc Inorganic materials 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
MWAYRGBWOVHDDZ-UHFFFAOYSA-N vanillic acid ethyl ester Natural products CCOC(=O)C1=CC=C(O)C(OC)=C1 MWAYRGBWOVHDDZ-UHFFFAOYSA-N 0.000 description 4
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 3
KJECIRFDWDJBDS-UHFFFAOYSA-N (2,3-dimethyl-3h-cyclopenta[b]pyran-2-yl)methanol Chemical compound O1C(CO)(C)C(C)C=C2C=CC=C21 KJECIRFDWDJBDS-UHFFFAOYSA-N 0.000 description 3
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 3
GFEKSRINNKUEIE-UHFFFAOYSA-N 2,3-dimethyl-1-benzofuran-5-carbaldehyde Chemical compound C1=C(C=O)C=C2C(C)=C(C)OC2=C1 GFEKSRINNKUEIE-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 3
ABAJWYUCHUGYCH-UHFFFAOYSA-N 4-(2,3-dimethyl-1-benzofuran-5-yl)piperidin-2-one Chemical compound C1=C2C(C)=C(C)OC2=CC=C1C1CCNC(=O)C1 ABAJWYUCHUGYCH-UHFFFAOYSA-N 0.000 description 3
QORRAUPOKIOIPA-UHFFFAOYSA-N 4-(2,3-dimethyl-1-benzofuran-5-yl)piperidine Chemical compound C1=C2C(C)=C(C)OC2=CC=C1C1CCNCC1 QORRAUPOKIOIPA-UHFFFAOYSA-N 0.000 description 3
XFQAHLNXRYGZQL-UHFFFAOYSA-N 4-(2,3-dimethyl-1-benzofuran-5-yl)piperidine;hydrochloride Chemical compound Cl.C1=C2C(C)=C(C)OC2=CC=C1C1CCNCC1 XFQAHLNXRYGZQL-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
229920002261 Corn starch Polymers 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
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230000002035 prolonged effect Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000005956 quaternization reaction Methods 0.000 description 1
239000011833 salt mixture Substances 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000000344 soap Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
XXFQGNXPWZSRRK-UHFFFAOYSA-N sodium;n-chlorobenzenesulfonamide Chemical compound [Na+].ClNS(=O)(=O)C1=CC=CC=C1 XXFQGNXPWZSRRK-UHFFFAOYSA-N 0.000 description 1
JERVILBAYMKXRX-UHFFFAOYSA-N sodium;tris(2-methoxyethoxy)alumane Chemical compound [Na].COCCO[Al](OCCOC)OCCOC JERVILBAYMKXRX-UHFFFAOYSA-N 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
150000003459 sulfonic acid esters Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
210000003568 synaptosome Anatomy 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000011289 tar acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000004853 tetrahydropyridinyl group Chemical class N1(CCCC=C1)* 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- 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
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Psychiatry (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

DD79213724A 1978-06-22 1979-06-19 Verfahren zur herstellung von neuen tetrahydropyridin-und piperidinderivaten DD144545A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH682378		1978-06-22

Publications (1)

Publication Number	Publication Date
DD144545A5 true DD144545A5 (de)	1980-10-22

Family

ID=4315581

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79213724A DD144545A5 (de)	1978-06-22	1979-06-19	Verfahren zur herstellung von neuen tetrahydropyridin-und piperidinderivaten

Country Status (10)

Country	Link
US (1)	US4259338A (fr)
EP (1)	EP0006524A1 (fr)
JP (1)	JPS552697A (fr)
AU (1)	AU523656B2 (fr)
CA (1)	CA1119601A (fr)
DD (1)	DD144545A5 (fr)
DK (1)	DK259879A (fr)
ES (3)	ES481714A1 (fr)
NZ (1)	NZ190784A (fr)
ZA (1)	ZA793091B (fr)

Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4495357A (en) *	1981-07-01	1985-01-22	The Upjohn Company	Pyridyl-substituted-benzofurans
US4490531A (en) *	1981-07-01	1984-12-25	The Upjohn Company	Pyridyl-substituted-benzofurans
US4455427A (en) *	1981-07-01	1984-06-19	The Upjohn Company	Pyridyl-substituted-benzofurans
US4447620A (en) *	1982-06-08	1984-05-08	The Upjohn Company	Imidazolyl-substituted benzothiophenes
US4452986A (en) *	1982-06-08	1984-06-05	The Upjohn Company	Imidazolyl-substituted benzofurans
US4430502A (en)	1982-08-13	1984-02-07	The Upjohn Company	Pyridinyl substituted benzimidazoles and quinoxalines
EP0106800A1 (fr) *	1982-10-08	1984-04-25	Ciba-Geigy Ag	Furannes
US4611059A (en) *	1982-10-12	1986-09-09	The Upjohn Company	Pyridyl-substituted benzothiophenes
US4855435A (en) *	1982-10-12	1989-08-08	The Upjohn Company	Pyridyl-substituted benzothiophenes
US5296497A (en) *	1989-05-16	1994-03-22	Duphar International Research B.V.	3,4-dehydropiperidine derivatives having psychotropic activity
EP0398413A1 (fr) *	1989-05-16	1990-11-22	Duphar International Research B.V	Dérivés de 3,4-déhydropipéridine à activité psychotrope
US5068359A (en) *	1989-06-20	1991-11-26	Ciba-Geigy Corporation	Microbicidal compositions
DE4017211A1 (de) *	1990-05-29	1991-12-05	Merck Patent Gmbh	Oxazolidinone
TW222631B (fr) *	1991-07-15	1994-04-21	Duphar Int Res
DE69418789T2 (de) *	1993-08-05	1999-12-02	Hoechst Marion Roussel, Inc.	2-(Piperidin-4-yl, Pyridin-4-yl und Tetrahydropyridin-4-yl)-benzofuran-7-carbamat Derivate, ihre Herstellung und Verwendung als Acetylcholinesterase Inhibitoren
JPH07320652A (ja) *	1994-05-27	1995-12-08	Toshiba Corp	カラー受像管及びシャドウマスクの製造方法
US5969146A (en) *	1995-10-11	1999-10-19	Synthelabo	Oxazolidin-2-one derivatives, preparation method therefor and therapeutical use thereof
FR2739856B1 (fr) *	1995-10-11	1997-11-14	Synthelabo	Derives de 3-benzofuranyloxazolidin-2-one, leur procede de preparation et leur application en therapeutique
FR2751653B1 (fr) *	1996-07-25	1998-09-04	Synthelabo	Derives de 3-benzofuranyloxazolidin-2-one, leur procede de preparation et leur application en therapeutique
FR2741072B1 (fr) *	1995-11-09	1997-12-12	Synthelabo	Derives d'oxazolidin-2-one, leur preparation et leur application en therapeutique
FR2741071B1 (fr) *	1995-11-09	1997-12-12	Synthelabo	Derives de 3-(benzofuran-5-yl)oxazolidin-2-one, leur preparation et leur application en therapeutique
CO5080791A1 (es)	1998-06-30	2001-09-25	Lilly Co Eli	Derivados de la piperidina que tienen efectos sobre sistemas con serotonina
GB9912413D0 (en)	1999-05-28	1999-07-28	Pfizer Ltd	Compounds useful in therapy
ES2198329T3 (es) *	1999-07-29	2004-02-01	Eli Lilly And Company	Agonistas de la serotonina benzofurilpiperazina.
EP1204654B1 (fr) *	1999-07-29	2003-07-23	Eli Lilly And Company	Benzofurylpiperazines: agonistes du recepteur 5-ht2c de la serotonine
DE60006825T2 (de) *	1999-07-29	2004-08-12	Eli Lilly And Co., Indianapolis	Serotonerge benzofurane
US6881733B1 (en)	1999-07-29	2005-04-19	Eli Lilly And Company	Serotonergic benzofurans
JP2005008631A (ja) *	2003-05-29	2005-01-13	New Industry Research Organization	ベンゾフラン化合物、およびそれを含有してなる医薬組成物
US7638540B2 (en)	2003-05-29	2009-12-29	The New Industry Research Organization	Benzofuran compound and medicinal composition containing the same
EP2110374A1 (fr) *	2008-04-18	2009-10-21	Merck Sante	Dérivés de benzofurane, benzothiophène, benzothiazol en tant que modulateurs FXR
CN101810606A (zh) *	2010-03-12	2010-08-25	南方医科大学	2-(6-羟基-2′,3′-二甲氧基苯基)-6-羟基-7-甲氧基苯骈呋喃在制备单胺氧化酶抑制剂中的应用
CN102381961B (zh) *	2011-09-03	2014-01-15	四川大学	3-苯基戊二酸类化合物、其制备方法和用途
CN118460017B (zh) *	2024-05-11	2024-11-05	广州豫顺新材料科技有限公司	一种覆铜板用改性球形硅微粉及其制备方法

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2633468A (en) *	1951-07-26	1953-03-31	Lilly Co Eli	Benzooxaheterocyclic bases and acid addition salts thereof
GB1041525A (en) *	1964-11-11	1966-09-07	Belge Produits Chimiques Sa	Benzofuran derivatives and processes for preparing the same
GB1139146A (en)	1966-10-10	1969-01-08	Belge Produits Chimiques Sa	Benzofuran derivatives and processes for preparing the same
US3751390A (en) *	1971-05-19	1973-08-07	Aldrich Chem Co Inc	Substituted dibenzofuran
BE794630A (fr) *	1972-01-26	1973-07-26	Beecham Group Ltd	Composes polycycliques antihypertenseurs
CH592656A5 (fr)	1973-03-02	1977-10-31	Ciba Geigy Ag
IE39264B1 (en) *	1973-05-25	1978-08-30	Ciba Geigy Ag	New pharmaceutical preparations
CH609054A5 (en) *	1975-11-26	1979-02-15	Ciba Geigy Ag	Process for the preparation of a novel piperidine derivative
CH609980A5 (en) *	1974-08-30	1979-03-30	Ciba Geigy Ag	Process for the preparation of novel piperidine derivatives
LU76756A1 (fr) *	1977-02-11	1978-10-18

1979
- 1979-06-11 EP EP79101887A patent/EP0006524A1/fr not_active Withdrawn
- 1979-06-19 DD DD79213724A patent/DD144545A5/de unknown
- 1979-06-20 CA CA000330210A patent/CA1119601A/fr not_active Expired
- 1979-06-20 ES ES481714A patent/ES481714A1/es not_active Expired
- 1979-06-21 AU AU48257/79A patent/AU523656B2/en not_active Expired - Fee Related
- 1979-06-21 NZ NZ190784A patent/NZ190784A/xx unknown
- 1979-06-21 DK DK259879A patent/DK259879A/da unknown
- 1979-06-21 ZA ZA793091A patent/ZA793091B/xx unknown
- 1979-06-22 JP JP7828279A patent/JPS552697A/ja active Pending
1980
- 1980-03-17 ES ES489627A patent/ES8104280A1/es not_active Expired
- 1980-03-17 ES ES489628A patent/ES8104281A1/es not_active Expired
- 1980-04-14 US US06/140,405 patent/US4259338A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA1119601A (fr)	1982-03-09
AU4825779A (en)	1980-01-03
US4259338A (en)	1981-03-31
ES489628A0 (es)	1981-04-01
ZA793091B (en)	1980-06-25
ES8104281A1 (es)	1981-04-01
ES489627A0 (es)	1981-04-01
AU523656B2 (en)	1982-08-05
ES481714A1 (es)	1980-06-16
EP0006524A1 (fr)	1980-01-09
ES8104280A1 (es)	1981-04-01
JPS552697A (en)	1980-01-10
NZ190784A (en)	1982-03-16
DK259879A (da)	1979-12-23

Publication	Publication Date	Title
DD144545A5 (de)	1980-10-22	Verfahren zur herstellung von neuen tetrahydropyridin-und piperidinderivaten
DE2614406C2 (fr)	1992-02-20
EP0084164B1 (fr)	1987-01-28	Dérivés d'amino-acides bicycliques, procédé pour leur préparation, agents les contenant et leur utilisation ainsi que des amino-acides bicycliques comme intermédiaires et procédé pour leur préparation
DD201793A5 (de)	1983-08-10	Verfahren zur herstellung von 6-hydroxy-2-(4-hydroxy-phenyl) 3-(4-(2-aminoethoxy)benzoyl)benzo(b)thiophenen
DE60128112T2 (de)	2007-12-27	Aminoalkoxybenzoyl-benzofurane oder benzothiophene, verfahren zu ihrer herstellung und die enthaltenden zusammensetzungen
DE3002367A1 (de)	1980-07-24	2-substituierte trans-5-aryl-2,3,4,4a,5, 9b-hexahydro-1h-pyrido eckige klammer auf 4,3-b eckige klammer zu indole
DD202542A5 (de)	1983-09-21	Verfahren zur herstellung von 1-phenyl-2-aminocarbonylindol-verbindungen
DE69102477T2 (de)	1995-02-09	3-Aminochroman-Derivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen.
DE2256392A1 (de)	1973-05-30	Verfahren zur herstellung neuer heterocyclischer verbindungen
GB2056435A (en)	1981-03-18	Novel Tetrahydropyridine and Piperidine Substituted Benzofuranes and Related Compounds
DE2737630C2 (fr)	1987-11-05
DE2038482A1 (de)	1971-02-18	Verfahren zur Herstellung neuer heterocyclischer Verbindungen
CH640212A5 (en)	1983-12-30	Process for the preparation of 1-amino-3-aryloxy-2-propanol derivatives
DE3424586A1 (de)	1986-01-09	3-aminocarbonylmethoxy-5-phenyl-pyrazol-verbindungen sowie verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE3300522C2 (fr)	1992-01-09
CH630903A5 (en)	1982-07-15	Process for preparing novel derivatives of 1,2,3,4,4a,10b-hexahydrobenzo(f)isoquinoline.
DE3520104A1 (de)	1985-12-12	Naphthoxazine, ihre herstellung und verwendung
DE2834372A1 (de)	1979-02-15	Perhydronaphthalinpentolderivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel
FR2703048A1 (fr)	1994-09-30	Nouveaux composés N-Benzylpiperazine, leur procédé de préparation et les compositions pharmaceutiques les renfermant.
AT383347B (de)	1987-06-25	Verfahren zur herstellung von neuen aren- und heteroarencarboxamidderivaten
DE2345192A1 (de)	1974-03-28	Verfahren zur herstellung neuer heterocyclischer verbindungen
DE3828869C2 (fr)	1990-07-19
DE69912282T2 (de)	2004-07-29	Verfahren zur herstellung eines indolderivates
CH634559A5 (de)	1983-02-15	Verfahren zur herstellung von 3-halogen-3-kohlenwasserstoffthio-oxindolen und verfahren zur herstellung von isatinen.
AT374175B (de)	1984-03-26	Verfahren zur herstellung von neuen pyrrolidin-, piperidin- und perhydroazepinderivaten und ihren saeureadditionssalzen