DD141308A5 - Verfahren zur herstellung von hexahydroazepin-,piperidin-und pyrrolidinderivaten - Google Patents

Verfahren zur herstellung von hexahydroazepin-,piperidin-und pyrrolidinderivaten Download PDF

Info

Publication number: DD141308A5
Authority: DD; German Democratic Republic
Prior art keywords: alkyl; hydrogen; general formula; lactam; compound
Prior art date: 1977-12-22

Application number

DD78209990A

Other languages

German (de)

English (en)

Inventor

John F Cavalla

Alan C White

Robin G Shepherd

Original Assignee

Wyeth John & Brother Ltd

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.)

1977-12-22

Filing date

1978-12-20

Publication date

1980-04-23

1978-12-20 Application filed by Wyeth John & Brother Ltd filed Critical Wyeth John & Brother Ltd

1980-04-23 Publication of DD141308A5 publication Critical patent/DD141308A5/de

Links

NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title description 16
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 title description 8
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title description 4
238000004519 manufacturing process Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 105
125000000217 alkyl group Chemical group 0.000 claims description 64
239000001257 hydrogen Substances 0.000 claims description 44
229910052739 hydrogen Inorganic materials 0.000 claims description 44
-1 alkyl lithium Chemical compound 0.000 claims description 30
238000000034 method Methods 0.000 claims description 27
125000003118 aryl group Chemical group 0.000 claims description 24
150000002431 hydrogen Chemical group 0.000 claims description 21
150000003951 lactams Chemical class 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
150000001450 anions Chemical class 0.000 claims description 9
229910052744 lithium Inorganic materials 0.000 claims description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
239000007858 starting material Substances 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 7
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
238000011065 in-situ storage Methods 0.000 claims description 5
229910052700 potassium Inorganic materials 0.000 claims description 5
239000011591 potassium Substances 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
239000011734 sodium Substances 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000000596 cyclohexenyl group Chemical class C1(=CCCCC1)* 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
239000007818 Grignard reagent Substances 0.000 claims description 2
229910000102 alkali metal hydride Inorganic materials 0.000 claims description 2
150000008046 alkali metal hydrides Chemical class 0.000 claims description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
150000004795 grignard reagents Chemical class 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
125000006239 protecting group Chemical group 0.000 claims description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
UODMSBYDFUPQHC-UHFFFAOYSA-M magnesium;di(propan-2-yl)azanide;bromide Chemical compound CC(C)N([Mg]Br)C(C)C UODMSBYDFUPQHC-UHFFFAOYSA-M 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 55
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
239000000243 solution Substances 0.000 description 40
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
239000000203 mixture Substances 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 26
239000003921 oil Substances 0.000 description 25
235000019198 oils Nutrition 0.000 description 25
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
239000002904 solvent Substances 0.000 description 19
239000011541 reaction mixture Substances 0.000 description 18
239000007787 solid Substances 0.000 description 16
238000004458 analytical method Methods 0.000 description 15
239000010410 layer Substances 0.000 description 15
239000000047 product Substances 0.000 description 15
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical group [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 14
239000000725 suspension Substances 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
229940043279 diisopropylamine Drugs 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 11
238000006243 chemical reaction Methods 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 11
125000003342 alkenyl group Chemical group 0.000 description 10
125000000304 alkynyl group Chemical group 0.000 description 10
DXZDEAJXVCLRLE-UHFFFAOYSA-N azepin-2-one Chemical compound O=C1C=CC=CC=N1 DXZDEAJXVCLRLE-UHFFFAOYSA-N 0.000 description 10
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 10
150000003235 pyrrolidines Chemical class 0.000 description 10
238000010992 reflux Methods 0.000 description 10
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 9
239000012044 organic layer Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
239000008346 aqueous phase Substances 0.000 description 8
239000000284 extract Substances 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
238000001816 cooling Methods 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
239000013078 crystal Substances 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000000463 material Substances 0.000 description 6
150000003053 piperidines Chemical class 0.000 description 6
GHNBWZWSJFIMQO-UHFFFAOYSA-N 3-methylazepin-2-one Chemical compound CC1=CC=CC=NC1=O GHNBWZWSJFIMQO-UHFFFAOYSA-N 0.000 description 5
JBKVHLHDHHXQEQ-UHFFFAOYSA-N Caprolactam Natural products O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
JFTPIEHHCQPVCS-UHFFFAOYSA-N 3-methoxycyclohex-2-en-1-one Chemical compound COC1=CC(=O)CCC1 JFTPIEHHCQPVCS-UHFFFAOYSA-N 0.000 description 4
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
IBNKFKLIUOMAQB-UHFFFAOYSA-N 3-(3-hydroxyphenyl)-1-methylazepan-2-one Chemical compound O=C1N(C)CCCCC1C1=CC=CC(O)=C1 IBNKFKLIUOMAQB-UHFFFAOYSA-N 0.000 description 3
IMCGYHPRALKTOL-UHFFFAOYSA-N 3-(3-hydroxyphenyl)azepan-2-one Chemical compound OC1=CC=CC(C2C(NCCCC2)=O)=C1 IMCGYHPRALKTOL-UHFFFAOYSA-N 0.000 description 3
IISFUJKHMFGYOU-UHFFFAOYSA-N 3-propan-2-yloxycyclohex-2-en-1-one Chemical compound CC(C)OC1=CC(=O)CCC1 IISFUJKHMFGYOU-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000001350 alkyl halides Chemical class 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
229940100198 alkylating agent Drugs 0.000 description 3
230000002152 alkylating effect Effects 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
239000002585 base Substances 0.000 description 3
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
238000005406 washing Methods 0.000 description 3
239000008096 xylene Substances 0.000 description 3
RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
XMSWGYQEWPUOKA-UHFFFAOYSA-N 2-[3-(3-hydroxyphenyl)-2,3-dimethylpiperidin-1-yl]-1-phenylethanone Chemical compound C1CCC(C=2C=C(O)C=CC=2)(C)C(C)N1CC(=O)C1=CC=CC=C1 XMSWGYQEWPUOKA-UHFFFAOYSA-N 0.000 description 2
VFUGCQKESINERB-UHFFFAOYSA-N 3-(1-methyl-3-propylpyrrolidin-3-yl)phenol Chemical compound C=1C=CC(O)=CC=1C1(CCC)CCN(C)C1 VFUGCQKESINERB-UHFFFAOYSA-N 0.000 description 2
UJLKWEKIONGLJO-UHFFFAOYSA-N 3-(3-hydroxyphenyl)-1-methylpyrrolidin-2-one Chemical compound O=C1N(C)CCC1C1=CC=CC(O)=C1 UJLKWEKIONGLJO-UHFFFAOYSA-N 0.000 description 2
HPYQDDXKEGCTGC-UHFFFAOYSA-N 3-(3-methoxyphenyl)-1-methylazepan-2-one Chemical compound COC1=CC=CC(C2C(N(C)CCCC2)=O)=C1 HPYQDDXKEGCTGC-UHFFFAOYSA-N 0.000 description 2
LDNFLWJRDDURLP-UHFFFAOYSA-N 3-(3-methoxyphenyl)azepan-2-one Chemical compound COC1=CC=CC(C2C(NCCCC2)=O)=C1 LDNFLWJRDDURLP-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
241000400611 Eucalyptus deanei Species 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
ZSSUKQHPALINBY-UHFFFAOYSA-N Secamine Natural products CCC1=CCCN(CCc2c3C(CCC(C(=O)OC)(c4[nH]c5ccccc5c4CCN6CCC=C(CC)C6)n3c7ccccc27)C(=O)OC)C1 ZSSUKQHPALINBY-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
230000000202 analgesic effect Effects 0.000 description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
229940073608 benzyl chloride Drugs 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
238000011081 inoculation Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
LVKCSZQWLOVUGB-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].C[CH-]C LVKCSZQWLOVUGB-UHFFFAOYSA-M 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
229950009273 myfadol Drugs 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
229950004859 profadol Drugs 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
238000012360 testing method Methods 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
DJGIITKNTHQYPX-UHFFFAOYSA-N 1-benzylazepan-2-one Chemical compound O=C1CCCCCN1CC1=CC=CC=C1 DJGIITKNTHQYPX-UHFFFAOYSA-N 0.000 description 1
BSXKVSVROCDONT-UHFFFAOYSA-N 1-ethyl-n-(2,4,4-trimethylpentan-2-yl)cyclohexan-1-amine Chemical compound CC(C)(C)CC(C)(C)NC1(CC)CCCCC1 BSXKVSVROCDONT-UHFFFAOYSA-N 0.000 description 1
XJZQHHIPUDRJGJ-UHFFFAOYSA-N 1-methyl-3-(3-oxocyclohexen-1-yl)azepan-2-one Chemical compound O=C1N(C)CCCCC1C1=CC(=O)CCC1 XJZQHHIPUDRJGJ-UHFFFAOYSA-N 0.000 description 1
YEVCQAHYSHCAQO-UHFFFAOYSA-N 1-methyl-3-(3-oxocyclohexen-1-yl)piperidin-2-one Chemical compound O=C1N(C)CCCC1C1=CC(=O)CCC1 YEVCQAHYSHCAQO-UHFFFAOYSA-N 0.000 description 1
FFTQILDGROVZHO-UHFFFAOYSA-N 1-methyl-3-(3-oxocyclohexen-1-yl)pyrrolidin-2-one Chemical compound O=C1N(C)CCC1C1=CC(=O)CCC1 FFTQILDGROVZHO-UHFFFAOYSA-N 0.000 description 1
ILKWEPWYWBCGSR-UHFFFAOYSA-N 1-methylazepine Chemical compound CN1C=CC=CC=C1 ILKWEPWYWBCGSR-UHFFFAOYSA-N 0.000 description 1
GGYVTHJIUNGKFZ-UHFFFAOYSA-N 1-methylpiperidin-2-one Chemical compound CN1CCCCC1=O GGYVTHJIUNGKFZ-UHFFFAOYSA-N 0.000 description 1
NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
VYGXREGKPDZFCE-UHFFFAOYSA-N 2-methyl-2H-azepine Chemical compound CC1N=CC=CC=C1 VYGXREGKPDZFCE-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
JLICHNCFTLFZJN-UHFFFAOYSA-N 3-(3-ethyl-1-methyl-3-azepanyl)phenol Chemical compound C=1C=CC(O)=CC=1C1(CC)CCCCN(C)C1 JLICHNCFTLFZJN-UHFFFAOYSA-N 0.000 description 1
NNRAHZOEQXAXAF-UHFFFAOYSA-N 3-(3-hydroxyphenyl)-1-methyl-3-propylpyrrolidin-2-one Chemical compound C=1C=CC(O)=CC=1C1(CCC)CCN(C)C1=O NNRAHZOEQXAXAF-UHFFFAOYSA-N 0.000 description 1
HNPRIQQMQGLGID-UHFFFAOYSA-N 3-(3-hydroxyphenyl)-1-methylpiperidin-2-one Chemical compound O=C1N(C)CCCC1C1=CC=CC(O)=C1 HNPRIQQMQGLGID-UHFFFAOYSA-N 0.000 description 1
ZVJNRZZSRMVBRS-UHFFFAOYSA-N 3-(3-methoxyphenyl)-1-methyl-3H-azepin-2-one Chemical compound COC=1C=C(C=CC=1)C1C(N(C=CC=C1)C)=O ZVJNRZZSRMVBRS-UHFFFAOYSA-N 0.000 description 1
TWJOWUPSYFIBKC-UHFFFAOYSA-N 3-(3-methoxyphenyl)azepane Chemical compound COC1=CC=CC(C2CNCCCC2)=C1 TWJOWUPSYFIBKC-UHFFFAOYSA-N 0.000 description 1
HZASYDHQJZKOCU-UHFFFAOYSA-N 3-(3-oxocyclohexen-1-yl)azepan-2-one Chemical compound O=C1CCCC(C2C(NCCCC2)=O)=C1 HZASYDHQJZKOCU-UHFFFAOYSA-N 0.000 description 1
PHWHMJKWJICNLX-UHFFFAOYSA-N 3-ethyl-1-methyl-3-(3-oxocyclohexen-1-yl)azepan-2-one Chemical compound C=1C(=O)CCCC=1C1(CC)CCCCN(C)C1=O PHWHMJKWJICNLX-UHFFFAOYSA-N 0.000 description 1
TWJZVJYUCAHEGB-UHFFFAOYSA-N 3-ethyl-1-methylazepan-2-one Chemical compound CCC1CCCCN(C)C1=O TWJZVJYUCAHEGB-UHFFFAOYSA-N 0.000 description 1
YFSJZMANJNLCOQ-UHFFFAOYSA-N 3-ethyl-3-(3-hydroxyphenyl)-1-methylazepan-2-one Chemical compound C=1C=CC(O)=CC=1C1(CC)CCCCN(C)C1=O YFSJZMANJNLCOQ-UHFFFAOYSA-N 0.000 description 1
AFBQUXAODCBPRJ-UHFFFAOYSA-N 3-ethyl-3-(3-methoxyphenyl)-1-methylazepan-2-one Chemical compound C=1C=CC(OC)=CC=1C1(CC)CCCCN(C)C1=O AFBQUXAODCBPRJ-UHFFFAOYSA-N 0.000 description 1
229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
244000166102 Eucalyptus leucoxylon Species 0.000 description 1
235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
101100345589 Mus musculus Mical1 gene Proteins 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
238000007126 N-alkylation reaction Methods 0.000 description 1
244000018764 Nyssa sylvatica Species 0.000 description 1
235000003339 Nyssa sylvatica Nutrition 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
150000001347 alkyl bromides Chemical class 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
238000010936 aqueous wash Methods 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229960003280 cupric chloride Drugs 0.000 description 1
150000001923 cyclic compounds Chemical class 0.000 description 1
FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
VGHOWOWLIXPTOA-UHFFFAOYSA-N cyclohexane;toluene Chemical compound C1CCCCC1.CC1=CC=CC=C1 VGHOWOWLIXPTOA-UHFFFAOYSA-N 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
239000002027 dichloromethane extract Substances 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
210000002196 fr. b Anatomy 0.000 description 1
210000003918 fraction a Anatomy 0.000 description 1
238000001030 gas--liquid chromatography Methods 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
238000007871 hydride transfer reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
JLICHNCFTLFZJN-HNNXBMFYSA-N meptazinol Chemical compound C=1C=CC(O)=CC=1[C@@]1(CC)CCCCN(C)C1 JLICHNCFTLFZJN-HNNXBMFYSA-N 0.000 description 1
229960000365 meptazinol Drugs 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
DLMICMXXVVMDNV-UHFFFAOYSA-N n,n-di(propan-2-yl)propan-1-amine Chemical compound CCCN(C(C)C)C(C)C DLMICMXXVVMDNV-UHFFFAOYSA-N 0.000 description 1
GMTCPFCMAHMEMT-UHFFFAOYSA-N n-decyldecan-1-amine Chemical compound CCCCCCCCCCNCCCCCCCCCC GMTCPFCMAHMEMT-UHFFFAOYSA-N 0.000 description 1
UYYCVBASZNFFRX-UHFFFAOYSA-N n-propan-2-ylcyclohexanamine Chemical compound CC(C)NC1CCCCC1 UYYCVBASZNFFRX-UHFFFAOYSA-N 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
KZOPSPQZLMCNPF-UHFFFAOYSA-N n-tert-butyl-2-methylbutan-2-amine Chemical compound CCC(C)(C)NC(C)(C)C KZOPSPQZLMCNPF-UHFFFAOYSA-N 0.000 description 1
CATWEXRJGNBIJD-UHFFFAOYSA-N n-tert-butyl-2-methylpropan-2-amine Chemical compound CC(C)(C)NC(C)(C)C CATWEXRJGNBIJD-UHFFFAOYSA-N 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000012545 processing Methods 0.000 description 1
238000006748 scratching Methods 0.000 description 1
230000002393 scratching effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000012485 toluene extract Substances 0.000 description 1
125000005389 trialkylsiloxy group Chemical group 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000001665 trituration Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 radicals, substituted by hetero atoms, attached to ring carbon 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
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- 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
- 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
- C07D211/72—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 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
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/04—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with only hydrogen atoms, halogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/08—Oxygen atoms
- C07D223/10—Oxygen atoms attached in position 2

Landscapes

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

DD78209990A 1977-12-22 1978-12-20 Verfahren zur herstellung von hexahydroazepin-,piperidin-und pyrrolidinderivaten DD141308A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB53370/77A GB1593888A (en)	1977-12-22	1977-12-22	Hexahydroazepine piperidine and pyrrolidine derivatives

Publications (1)

Publication Number	Publication Date
DD141308A5 true DD141308A5 (de)	1980-04-23

Family

ID=10467561

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DD78209990A DD141308A5 (de)	1977-12-22	1978-12-20	Verfahren zur herstellung von hexahydroazepin-,piperidin-und pyrrolidinderivaten
DD78219713A DD149515A5 (de)	1977-12-22	1978-12-20	Verfahren zur herstellung von hexahydroazepin-,piperidin-und pyrrolidinderivaten

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DD78219713A DD149515A5 (de)	1977-12-22	1978-12-20	Verfahren zur herstellung von hexahydroazepin-,piperidin-und pyrrolidinderivaten

Country Status (33)

Country	Link
US (2)	US4197239A (pl)
EP (1)	EP0003253B1 (pl)
JP (1)	JPS5488286A (pl)
AR (1)	AR221710A1 (pl)
AT (1)	AT373586B (pl)
AU (1)	AU519653B2 (pl)
CA (2)	CA1113092A (pl)
CS (1)	CS207748B2 (pl)
CY (2)	CY1144A (pl)
DD (2)	DD141308A5 (pl)
DE (1)	DE2862139D1 (pl)
DK (1)	DK156302C (pl)
EG (1)	EG13745A (pl)
ES (2)	ES476160A1 (pl)
FI (1)	FI70575C (pl)
GB (1)	GB1593888A (pl)
GR (1)	GR64029B (pl)
HK (2)	HK18182A (pl)
HU (1)	HU181997B (pl)
IE (1)	IE47631B1 (pl)
IL (1)	IL55924A (pl)
IN (1)	IN150193B (pl)
IT (1)	IT1102761B (pl)
KE (2)	KE3207A (pl)
MX (1)	MX5628E (pl)
MY (2)	MY8200278A (pl)
NZ (1)	NZ188863A (pl)
PH (2)	PH14412A (pl)
PL (1)	PL126008B1 (pl)
PT (1)	PT68962A (pl)
SU (1)	SU1301311A3 (pl)
YU (1)	YU40543B (pl)
ZA (1)	ZA786244B (pl)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE11046T1 (de) *	1979-07-03	1985-01-15	John Wyeth & Brother Limited	Verfahren zur herstellung von 2-oxo- und 2unsubstituierten hexahydroazepinderivaten.
IE54154B1 (en) *	1981-12-02	1989-07-05	Wyeth John & Brother Ltd	M-hydroxyphenyl substituted compounds
US5665754A (en) *	1993-09-20	1997-09-09	Glaxo Wellcome Inc.	Substituted pyrrolidines
SE0001438D0 (sv)	2000-04-18	2000-04-18	Axon Chemicals Bv	New chemical compounds and their use in therapy
KR100421282B1 (ko) *	2001-08-22	2004-03-09	부광약품 주식회사	1-메틸헥사히드로-4-아제피논 염산염의 제조방법
RU2378258C2 (ru) *	2004-07-13	2010-01-10	Ф. Хоффманн-Ля Рош Аг	Производные сульфонамида

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2524643A (en) *	1947-12-04	1950-10-03	Maltbie Lab Inc	3-phenyl-2-piperidones
US3149123A (en) *	1961-01-04	1964-09-15	Parke Davis & Co	1, 3-dialkyl-3-oxyphenylpyrrolidine compounds
NL265485A (pl) *	1961-06-02
FR1337793A (fr) *	1962-06-19	1963-09-20	Parke Davis & Co	Composés de pyrrolidine et procédé de préparation de ces composés
GB1285025A (en) *	1968-08-16	1972-08-09	Wyeth John & Brother Ltd	Hexahydroazepines
CH526535A (de) *	1970-02-05	1972-08-15	Sandoz Ag	Verfahren zur Herstellung neuer Pyrrolidin-1-carboxamidinderivate
CH526536A (de) *	1970-02-05	1972-08-15	Sandoz Ag	Verfahren zur Herstellung neuer 3-Phenylpyrrolidinderivate
CH526534A (de) *	1970-02-05	1972-08-15	Sandoz Ag	Verfahren zur Herstellung neuer Pyrrolidin-1-carboxamidinderivate
US3729465A (en) *	1971-02-03	1973-04-24	Wyeth John & Brother Ltd	Hexahydroazepines
JPS4911844A (pl) *	1972-05-09	1974-02-01
BE850777A (fr) *	1976-01-28	1977-07-26	Sandoz Sa	Nouveaux derives de la pyrrolidine

1977
- 1977-12-22 GB GB53370/77A patent/GB1593888A/en not_active Expired
1978
- 1978-05-30 CY CY1144A patent/CY1144A/en unknown
- 1978-05-30 CY CY1145A patent/CY1145A/en unknown
- 1978-11-06 ZA ZA786244A patent/ZA786244B/xx unknown
- 1978-11-08 NZ NZ188863A patent/NZ188863A/xx unknown
- 1978-11-09 CA CA316,049A patent/CA1113092A/en not_active Expired
- 1978-11-09 CA CA316,048A patent/CA1113465A/en not_active Expired
- 1978-11-10 AU AU41479/78A patent/AU519653B2/en not_active Expired
- 1978-11-10 IL IL55924A patent/IL55924A/xx unknown
- 1978-11-15 US US05/961,086 patent/US4197239A/en not_active Expired - Lifetime
- 1978-11-15 IE IE2252/78A patent/IE47631B1/en unknown
- 1978-11-15 US US05/961,087 patent/US4197241A/en not_active Expired - Lifetime
- 1978-11-20 IN IN1249/CAL/78A patent/IN150193B/en unknown
- 1978-11-28 AR AR274561A patent/AR221710A1/es active
- 1978-11-30 DK DK546578A patent/DK156302C/da not_active IP Right Cessation
- 1978-11-30 MX MX787562U patent/MX5628E/es unknown
- 1978-12-06 DE DE7878300753T patent/DE2862139D1/de not_active Expired
- 1978-12-06 EP EP78300753A patent/EP0003253B1/en not_active Expired
- 1978-12-08 PH PH21913A patent/PH14412A/en unknown
- 1978-12-08 PH PH21914A patent/PH14517A/en unknown
- 1978-12-15 AT AT0898578A patent/AT373586B/de not_active IP Right Cessation
- 1978-12-19 GR GR57927A patent/GR64029B/el unknown
- 1978-12-19 YU YU2997/78A patent/YU40543B/xx unknown
- 1978-12-20 EG EG724/78A patent/EG13745A/xx active
- 1978-12-20 PL PL1978211970A patent/PL126008B1/pl unknown
- 1978-12-20 DD DD78209990A patent/DD141308A5/de unknown
- 1978-12-20 DD DD78219713A patent/DD149515A5/de unknown
- 1978-12-20 SU SU782699100A patent/SU1301311A3/ru active
- 1978-12-20 FI FI783922A patent/FI70575C/fi not_active IP Right Cessation
- 1978-12-20 ES ES476160A patent/ES476160A1/es not_active Expired
- 1978-12-21 JP JP15695778A patent/JPS5488286A/ja active Granted
- 1978-12-21 PT PT68962A patent/PT68962A/pt unknown
- 1978-12-21 HU HU78WI298A patent/HU181997B/hu unknown
- 1978-12-21 CS CS788756A patent/CS207748B2/cs unknown
- 1978-12-22 IT IT31286/78A patent/IT1102761B/it active
1979
- 1979-05-31 ES ES481125A patent/ES481125A1/es not_active Expired
1982
- 1982-04-06 KE KE3207A patent/KE3207A/xx unknown
- 1982-04-06 KE KE3206A patent/KE3206A/xx unknown
- 1982-04-29 HK HK181/82A patent/HK18182A/en not_active IP Right Cessation
- 1982-04-29 HK HK180/82A patent/HK18082A/xx not_active IP Right Cessation
- 1982-12-30 MY MY278/82A patent/MY8200278A/xx unknown
- 1982-12-30 MY MY279/82A patent/MY8200279A/xx unknown

Also Published As

Publication number	Publication date
CS207748B2 (en)	1981-08-31
SU1301311A3 (ru)	1987-03-30
CY1144A (en)	1982-09-10
MX5628E (es)	1983-11-15
PH14517A (en)	1981-08-26
KE3207A (en)	1982-05-21
CA1113465A (en)	1981-12-01
IT7831286A0 (it)	1978-12-22
PT68962A (en)	1979-01-01
IL55924A0 (en)	1979-01-31
US4197239A (en)	1980-04-08
IN150193B (pl)	1982-08-14
DK156302C (da)	1989-12-11
PH14412A (en)	1981-07-09
HK18082A (en)	1982-05-07
ZA786244B (en)	1980-06-25
FI70575B (fi)	1986-06-06
FI783922A7 (fi)	1979-06-23
DD149515A5 (de)	1981-07-15
IT1102761B (it)	1985-10-07
GB1593888A (en)	1981-07-22
AU4147978A (en)	1979-06-28
MY8200279A (en)	1982-12-31
ES476160A1 (es)	1979-11-16
PL126008B1 (en)	1983-06-30
JPS64392B2 (pl)	1989-01-06
NZ188863A (en)	1982-03-16
EP0003253B1 (en)	1982-12-22
HU181997B (en)	1983-11-28
EG13745A (en)	1983-03-31
YU299778A (en)	1983-12-31
AT373586B (de)	1984-02-10
GR64029B (en)	1980-01-19
FI70575C (fi)	1986-09-24
IE47631B1 (en)	1984-05-16
ES481125A1 (es)	1980-02-01
ATA898578A (de)	1983-06-15
JPS5488286A (en)	1979-07-13
MY8200278A (en)	1982-12-31
DK546578A (da)	1979-06-23
YU40543B (en)	1986-02-28
US4197241A (en)	1980-04-08
AU519653B2 (en)	1981-12-17
CA1113092A (en)	1981-11-24
PL211970A1 (pl)	1980-02-25
DK156302B (da)	1989-07-31
HK18182A (en)	1982-05-07
AR221710A1 (es)	1981-03-13
DE2862139D1 (en)	1983-01-27
IL55924A (en)	1982-01-31
KE3206A (en)	1982-05-21
IE782252L (en)	1979-06-22
CY1145A (en)	1982-09-10
EP0003253A1 (en)	1979-08-08

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CH638525A5 (de)	1983-09-30	3-(tetrazol-5-yl)-1-azaxanthone und verfahren zu ihrer herstellung.
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