CH629188A5 - Process for the preparation of pyrrolidine derivatives - Google Patents
Process for the preparation of pyrrolidine derivatives Download PDFInfo
- Publication number
- CH629188A5 CH629188A5 CH746077A CH746077A CH629188A5 CH 629188 A5 CH629188 A5 CH 629188A5 CH 746077 A CH746077 A CH 746077A CH 746077 A CH746077 A CH 746077A CH 629188 A5 CH629188 A5 CH 629188A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- phenyl
- substituted
- compound
- compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 6
- 150000003235 pyrrolidines Chemical class 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 17
- -1 nitro-substituted phenyl Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 239000007858 starting material Substances 0.000 claims description 12
- 150000001204 N-oxides Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000001302 tertiary amino group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- IOXBBNAZFRKICN-UHFFFAOYSA-N 5-(4-methoxyphenyl)-2,2-dimethyl-3-thiophen-2-ylpyrrolidine Chemical compound C1=CC(OC)=CC=C1C1NC(C)(C)C(C=2SC=CC=2)C1 IOXBBNAZFRKICN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 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 2
- 125000003275 alpha amino acid group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000243 solution Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- 239000011701 zinc Substances 0.000 description 8
- 229910052725 zinc Inorganic materials 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 235000019253 formic acid Nutrition 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000010802 sludge Substances 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- PVFZEEVDTPRFHF-UHFFFAOYSA-N 4-(2,2-dimethyl-1-oxido-5-phenyl-3,4-dihydropyrrol-1-ium-3-yl)-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1C(C)(C)[N+]([O-])=C(C=2C=CC=CC=2)C1 PVFZEEVDTPRFHF-UHFFFAOYSA-N 0.000 description 3
- UEXOUTLYWZIKPB-UHFFFAOYSA-N 4-[5-(4-methoxyphenyl)-2,2-dimethyl-3,4-dihydropyrrol-3-yl]-n,n-dimethylaniline;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1=NC(C)(C)C(C=2C=CC(=CC=2)N(C)C)C1 UEXOUTLYWZIKPB-UHFFFAOYSA-N 0.000 description 3
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- DGUBJHVIQRDVSA-UHFFFAOYSA-N 1-(4-methoxyphenyl)-4-methyl-4-nitro-3-thiophen-2-ylpentan-1-one Chemical compound C1=CC(OC)=CC=C1C(=O)CC(C(C)(C)[N+]([O-])=O)C1=CC=CS1 DGUBJHVIQRDVSA-UHFFFAOYSA-N 0.000 description 2
- YLTKTAIFVUHXLR-UHFFFAOYSA-N 3-(4-methoxythiophen-2-yl)-1-phenylprop-2-en-1-one Chemical compound COC1=CSC(C=CC(=O)C=2C=CC=CC=2)=C1 YLTKTAIFVUHXLR-UHFFFAOYSA-N 0.000 description 2
- LSEZPQGYIKXUDL-UHFFFAOYSA-N 4-(2,2-dimethyl-5-phenyl-3,4-dihydropyrrol-3-yl)-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1C(C)(C)N=C(C=2C=CC=CC=2)C1 LSEZPQGYIKXUDL-UHFFFAOYSA-N 0.000 description 2
- AAKITRDXVMXHAO-UHFFFAOYSA-N 5-(4-methoxyphenyl)-2,2-dimethyl-3-thiophen-2-yl-3,4-dihydropyrrole Chemical compound C1=CC(OC)=CC=C1C1=NC(C)(C)C(C=2SC=CC=2)C1 AAKITRDXVMXHAO-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- WULJZHLUFBFHCR-LIOBNPLQSA-N (3s,5s)-5-(4-methoxyphenyl)-2,2-dimethyl-3-thiophen-2-ylpyrrolidine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1[C@H]1NC(C)(C)[C@@H](C=2SC=CC=2)C1 WULJZHLUFBFHCR-LIOBNPLQSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 1
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- UUGGQJHXHOOWPY-RTBURBONSA-N 4-[(3r,5r)-2,2-dimethyl-5-phenylpyrrolidin-3-yl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1[C@@H]1C(C)(C)N[C@@H](C=2C=CC=CC=2)C1 UUGGQJHXHOOWPY-RTBURBONSA-N 0.000 description 1
- NDFGPNJTWSPVSO-UHFFFAOYSA-N 4-[5-(4-methoxyphenyl)-2,2-dimethyl-1-oxido-3,4-dihydropyrrol-1-ium-3-yl]-n,n-dimethylaniline Chemical compound C1=CC(OC)=CC=C1C1=[N+]([O-])C(C)(C)C(C=2C=CC(=CC=2)N(C)C)C1 NDFGPNJTWSPVSO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- 229920002472 Starch Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- AYLIEDQYYJIGDP-UHFFFAOYSA-N [C]1=CC=CS1 Chemical compound [C]1=CC=CS1 AYLIEDQYYJIGDP-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
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- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
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- 239000012433 hydrogen halide Substances 0.000 description 1
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- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Inorganic materials Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 1
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- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- 238000006396 nitration reaction Methods 0.000 description 1
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- AAZYNPCMLRQUHI-UHFFFAOYSA-N propan-2-one;2-propan-2-yloxypropane Chemical compound CC(C)=O.CC(C)OC(C)C AAZYNPCMLRQUHI-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- XKGLSKVNOSHTAD-UHFFFAOYSA-N valerophenone Chemical compound CCCCC(=O)C1=CC=CC=C1 XKGLSKVNOSHTAD-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH414081A CH629484A5 (en) | 1977-06-17 | 1981-06-23 | Heterocyclic compounds. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT549076A AT355012B (de) | 1976-07-26 | 1976-07-26 | Verfahren zur herstellung von neuen pyrrolidin- derivaten, ihren racematen, optischen anti- poden, den cis- und trans-isomeren und deren gemischen und saeureadditionssalzen hievon |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH629188A5 true CH629188A5 (en) | 1982-04-15 |
Family
ID=3576384
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH746077A CH629188A5 (en) | 1976-07-26 | 1977-06-17 | Process for the preparation of pyrrolidine derivatives |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS5315365A (enExample) |
| AR (1) | AR220682A1 (enExample) |
| AT (1) | AT355012B (enExample) |
| AU (1) | AU512688B2 (enExample) |
| BE (1) | BE857098A (enExample) |
| CH (1) | CH629188A5 (enExample) |
| DE (1) | DE2733232A1 (enExample) |
| DK (1) | DK333877A (enExample) |
| ES (1) | ES460993A1 (enExample) |
| FI (1) | FI772269A7 (enExample) |
| FR (1) | FR2359824A1 (enExample) |
| GB (1) | GB1564656A (enExample) |
| GR (1) | GR72106B (enExample) |
| HU (1) | HU174926B (enExample) |
| IE (1) | IE45171B1 (enExample) |
| IL (1) | IL52557A (enExample) |
| IT (1) | IT1143737B (enExample) |
| LU (1) | LU77826A1 (enExample) |
| MC (1) | MC1158A1 (enExample) |
| NL (1) | NL7708280A (enExample) |
| NO (1) | NO146467C (enExample) |
| NZ (1) | NZ184691A (enExample) |
| PH (1) | PH12499A (enExample) |
| PT (1) | PT66845B (enExample) |
| SE (1) | SE424988B (enExample) |
| ZA (1) | ZA774345B (enExample) |
-
1976
- 1976-07-26 AT AT549076A patent/AT355012B/de not_active IP Right Cessation
-
1977
- 1977-06-17 CH CH746077A patent/CH629188A5/de not_active IP Right Cessation
- 1977-06-30 IT IT25264/77A patent/IT1143737B/it active
- 1977-07-01 GR GR54020A patent/GR72106B/el unknown
- 1977-07-19 ZA ZA00774345A patent/ZA774345B/xx unknown
- 1977-07-19 IL IL52557A patent/IL52557A/xx unknown
- 1977-07-20 IE IE1518/77A patent/IE45171B1/en unknown
- 1977-07-20 NZ NZ184691A patent/NZ184691A/xx unknown
- 1977-07-20 AU AU27158/77A patent/AU512688B2/en not_active Expired
- 1977-07-21 MC MC771253A patent/MC1158A1/fr unknown
- 1977-07-22 NO NO772626A patent/NO146467C/no unknown
- 1977-07-22 DE DE19772733232 patent/DE2733232A1/de not_active Withdrawn
- 1977-07-22 AR AR268536A patent/AR220682A1/es active
- 1977-07-22 JP JP8750577A patent/JPS5315365A/ja active Pending
- 1977-07-22 FR FR7722582A patent/FR2359824A1/fr active Granted
- 1977-07-22 HU HU77HO2005A patent/HU174926B/hu unknown
- 1977-07-22 LU LU77826A patent/LU77826A1/xx unknown
- 1977-07-22 DK DK333877A patent/DK333877A/da not_active Application Discontinuation
- 1977-07-23 ES ES460993A patent/ES460993A1/es not_active Expired
- 1977-07-25 BE BE179585A patent/BE857098A/xx unknown
- 1977-07-25 SE SE7708536A patent/SE424988B/xx unknown
- 1977-07-25 PT PT66845A patent/PT66845B/pt unknown
- 1977-07-25 GB GB31113/77A patent/GB1564656A/en not_active Expired
- 1977-07-25 FI FI772269A patent/FI772269A7/fi not_active Application Discontinuation
- 1977-07-26 NL NL7708280A patent/NL7708280A/xx not_active Application Discontinuation
- 1977-07-26 PH PH20033A patent/PH12499A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE424988B (sv) | 1982-08-23 |
| GB1564656A (en) | 1980-04-10 |
| DE2733232A1 (de) | 1978-02-09 |
| ATA549076A (de) | 1979-07-15 |
| AT355012B (de) | 1980-02-11 |
| NZ184691A (en) | 1980-05-08 |
| BE857098A (fr) | 1978-01-25 |
| JPS5315365A (en) | 1978-02-13 |
| FI772269A7 (enExample) | 1978-01-27 |
| LU77826A1 (enExample) | 1978-09-14 |
| FR2359824B1 (enExample) | 1981-01-09 |
| HU174926B (hu) | 1980-04-28 |
| MC1158A1 (fr) | 1978-04-17 |
| NO772626L (no) | 1978-01-27 |
| IE45171L (en) | 1978-01-26 |
| PH12499A (en) | 1979-04-05 |
| ZA774345B (en) | 1978-06-28 |
| NO146467C (no) | 1982-10-06 |
| AR220682A1 (es) | 1980-11-28 |
| IL52557A (en) | 1980-02-29 |
| AU512688B2 (en) | 1980-10-23 |
| IE45171B1 (en) | 1982-06-30 |
| IL52557A0 (en) | 1977-10-31 |
| FR2359824A1 (fr) | 1978-02-24 |
| PT66845B (en) | 1979-06-07 |
| DK333877A (da) | 1978-01-27 |
| ES460993A1 (es) | 1978-05-01 |
| AU2715877A (en) | 1979-01-25 |
| NO146467B (no) | 1982-06-28 |
| SE7708536L (sv) | 1978-01-27 |
| IT1143737B (it) | 1986-10-22 |
| NL7708280A (nl) | 1978-01-30 |
| PT66845A (en) | 1977-08-01 |
| GR72106B (enExample) | 1983-09-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |