NO771422L - Fremgangsm}te for fremstilling av tetramisol, levamisol og derivater derav - Google Patents

Fremgangsm}te for fremstilling av tetramisol, levamisol og derivater derav

Info

Publication number: NO771422L
Authority: NO; Norway
Prior art keywords: phenyl; methoxyethyl; formula; imidazolidone; imidazolin
Prior art date: 1976-04-26

Application number

NO771422A

Other languages

English (en)

Norwegian (no)

Inventor

Sivaraman Raghu

Arthur Kentaro Hoffmann

Balwant Singh

Original Assignee

American Cyanamid Co

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.)

1976-04-26

Filing date

1977-04-25

Publication date

1977-10-27

1976-11-08 Priority claimed from US05/739,924 external-priority patent/US4090025A/en

1977-04-25 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1977-10-27 Publication of NO771422L publication Critical patent/NO771422L/no

Links

238000000034 method Methods 0.000 title claims description 24
238000002360 preparation method Methods 0.000 title claims description 13
HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 title description 10
229960001614 levamisole Drugs 0.000 title description 9
150000001875 compounds Chemical class 0.000 claims description 46
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
239000002904 solvent Substances 0.000 claims description 25
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
-1 acyl anhydride Chemical class 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
239000003054 catalyst Substances 0.000 claims description 15
CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 claims description 11
YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
239000011593 sulfur Substances 0.000 claims description 7
UXERCGOLBABXTB-UHFFFAOYSA-N 3-(2-methoxyethyl)-5-phenyl-1h-imidazol-2-one Chemical compound N1C(=O)N(CCOC)C=C1C1=CC=CC=C1 UXERCGOLBABXTB-UHFFFAOYSA-N 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
239000003153 chemical reaction reagent Substances 0.000 claims description 5
150000002431 hydrogen Chemical group 0.000 claims description 5
238000005984 hydrogenation reaction Methods 0.000 claims description 5
239000012434 nucleophilic reagent Substances 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
JHALJJCMBMHOMB-UHFFFAOYSA-N 1-(2-hydroxyethyl)-4-phenylimidazolidin-2-one Chemical compound N1C(=O)N(CCO)CC1C1=CC=CC=C1 JHALJJCMBMHOMB-UHFFFAOYSA-N 0.000 claims description 4
SAUCUHKFBAYUJF-UHFFFAOYSA-N 2-(2-oxo-4-phenylimidazolidin-1-yl)ethyl acetate Chemical compound N1C(=O)N(CCOC(=O)C)CC1C1=CC=CC=C1 SAUCUHKFBAYUJF-UHFFFAOYSA-N 0.000 claims description 4
IMLSCHKGHPZCRB-UHFFFAOYSA-N 2-(2-oxo-5-phenyl-1h-imidazol-3-yl)ethyl acetate Chemical compound N1C(=O)N(CCOC(=O)C)C=C1C1=CC=CC=C1 IMLSCHKGHPZCRB-UHFFFAOYSA-N 0.000 claims description 4
239000004215 Carbon black (E152) Substances 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
XJDMWEBCUKGNMW-UHFFFAOYSA-N 3-(2-butoxyethyl)-5-phenyl-1h-imidazol-2-one Chemical compound N1C(=O)N(CCOCCCC)C=C1C1=CC=CC=C1 XJDMWEBCUKGNMW-UHFFFAOYSA-N 0.000 claims description 3
DYXLJVBGQMMTHR-UHFFFAOYSA-N 3-acetyl-1-(2-methoxyethyl)-4-phenylimidazol-2-one Chemical compound CC(=O)N1C(=O)N(CCOC)C=C1C1=CC=CC=C1 DYXLJVBGQMMTHR-UHFFFAOYSA-N 0.000 claims description 3
BVHHMHMXFWJGOF-UHFFFAOYSA-N 3-acetyl-1-(2-methoxyethyl)-4-phenylimidazolidin-2-one Chemical compound CC(=O)N1C(=O)N(CCOC)CC1C1=CC=CC=C1 BVHHMHMXFWJGOF-UHFFFAOYSA-N 0.000 claims description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
239000012458 free base Substances 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
150000002430 hydrocarbons Chemical class 0.000 claims description 3
238000010992 reflux Methods 0.000 claims description 3
HAHTWNTVJQGVLH-UHFFFAOYSA-N 1-(2-butoxyethyl)-4-phenylimidazolidin-2-one Chemical compound N1C(=O)N(CCOCCCC)CC1C1=CC=CC=C1 HAHTWNTVJQGVLH-UHFFFAOYSA-N 0.000 claims description 2
CALKKCCPRZLOLZ-UHFFFAOYSA-N 1-(2-methoxyethyl)-4-(3-methoxyphenyl)imidazolidin-2-one Chemical compound N1C(=O)N(CCOC)CC1C1=CC=CC(OC)=C1 CALKKCCPRZLOLZ-UHFFFAOYSA-N 0.000 claims description 2
COHVXEPINWPACP-UHFFFAOYSA-N 2-(2-oxo-4-phenylimidazolidin-1-yl)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCN(C(N1)=O)CC1C1=CC=CC=C1 COHVXEPINWPACP-UHFFFAOYSA-N 0.000 claims description 2
MGGQHZLAIXIXRO-UHFFFAOYSA-N 3-(2-methoxybenzoyl)-1-(2-methoxyethyl)-4-phenylimidazol-2-one Chemical compound C=1C=CC=C(OC)C=1C(=O)N1C(=O)N(CCOC)C=C1C1=CC=CC=C1 MGGQHZLAIXIXRO-UHFFFAOYSA-N 0.000 claims description 2
JPJBBFTVJDPHBH-UHFFFAOYSA-N 3-(adamantane-1-carbonyl)-1-(2-methoxyethyl)-4-phenylimidazol-2-one Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)N1C(=O)N(CCOC)C=C1C1=CC=CC=C1 JPJBBFTVJDPHBH-UHFFFAOYSA-N 0.000 claims description 2
GRKCNKCWEWUOAB-UHFFFAOYSA-N 3-(adamantane-1-carbonyl)-1-(2-methoxyethyl)-4-phenylimidazolidin-2-one Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)N1C(=O)N(CCOC)CC1C1=CC=CC=C1 GRKCNKCWEWUOAB-UHFFFAOYSA-N 0.000 claims description 2
IWEKDEBYEUTNSR-UHFFFAOYSA-N 3-(cyclohexanecarbonyl)-1-(2-methoxyethyl)-4-phenylimidazol-2-one Chemical compound C1CCCCC1C(=O)N1C(=O)N(CCOC)C=C1C1=CC=CC=C1 IWEKDEBYEUTNSR-UHFFFAOYSA-N 0.000 claims description 2
WUUSKKYXRAMVAT-UHFFFAOYSA-N 3-(cyclohexanecarbonyl)-1-(2-methoxyethyl)-4-phenylimidazolidin-2-one Chemical compound O=C1N(CCOC)CC(C=2C=CC=CC=2)N1C(=O)C1CCCCC1 WUUSKKYXRAMVAT-UHFFFAOYSA-N 0.000 claims description 2
MZUSRFLDXOQVIK-UHFFFAOYSA-N 3-benzoyl-1-(2-methoxyethyl)-4-phenylimidazolidin-2-one Chemical compound O=C1N(CCOC)CC(C=2C=CC=CC=2)N1C(=O)C1=CC=CC=C1 MZUSRFLDXOQVIK-UHFFFAOYSA-N 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
150000001266 acyl halides Chemical class 0.000 claims description 2
150000001450 anions Chemical class 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-O oxonium Chemical compound [OH3+] XLYOFNOQVPJJNP-UHFFFAOYSA-O 0.000 claims description 2
229910052763 palladium Inorganic materials 0.000 claims description 2
229910052697 platinum Inorganic materials 0.000 claims description 2
150000003512 tertiary amines Chemical class 0.000 claims description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
CCPSXQZBFJNUQC-UHFFFAOYSA-N 1-(2-butoxyethyl)-4-phenylimidazolidine-2-thione Chemical compound N1C(=S)N(CCOCCCC)CC1C1=CC=CC=C1 CCPSXQZBFJNUQC-UHFFFAOYSA-N 0.000 claims 1
LYLHYXVUJHVIEQ-UHFFFAOYSA-N 1-(2-methoxyethyl)-4-phenyl-3-[4-(trifluoromethyl)benzoyl]imidazol-2-one Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(=O)N1C(=O)N(CCOC)C=C1C1=CC=CC=C1 LYLHYXVUJHVIEQ-UHFFFAOYSA-N 0.000 claims 1
YBIDGBUFMFZYSV-UHFFFAOYSA-N 1-(2-phenoxyethyl)-4-phenylimidazolidine-2-thione Chemical compound S=C1NC(C=2C=CC=CC=2)CN1CCOC1=CC=CC=C1 YBIDGBUFMFZYSV-UHFFFAOYSA-N 0.000 claims 1
VOHOBUIFWGMDRU-UHFFFAOYSA-N 3-(2-methoxyethyl)-5-(3-methoxyphenyl)-1H-imidazol-2-one Chemical compound N1C(=O)N(CCOC)C=C1C1=CC=CC(OC)=C1 VOHOBUIFWGMDRU-UHFFFAOYSA-N 0.000 claims 1
QFVAZQWRPGRERC-UHFFFAOYSA-N 3-acetyl-1-(2-butoxyethyl)-4-phenylimidazolidin-2-one Chemical compound CC(=O)N1C(=O)N(CCOCCCC)CC1C1=CC=CC=C1 QFVAZQWRPGRERC-UHFFFAOYSA-N 0.000 claims 1
XGJZRQDBEJOXRY-UHFFFAOYSA-N 4-(3-bromophenyl)-1-(2-methoxyethyl)imidazolidin-2-one Chemical compound N1C(=O)N(CCOC)CC1C1=CC=CC(Br)=C1 XGJZRQDBEJOXRY-UHFFFAOYSA-N 0.000 claims 1
IBSPMXQCGKUNEQ-UHFFFAOYSA-N 5-(3-bromophenyl)-3-(2-methoxyethyl)-1h-imidazol-2-one Chemical compound N1C(=O)N(CCOC)C=C1C1=CC=CC(Br)=C1 IBSPMXQCGKUNEQ-UHFFFAOYSA-N 0.000 claims 1
101150047265 COR2 gene Proteins 0.000 claims 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
101100295741 Gallus gallus COR4 gene Proteins 0.000 claims 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
101100467189 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) QCR2 gene Proteins 0.000 claims 1
239000005864 Sulphur Substances 0.000 claims 1
239000002585 base Substances 0.000 claims 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
229910017052 cobalt Inorganic materials 0.000 claims 1
239000010941 cobalt Substances 0.000 claims 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
229910052741 iridium Inorganic materials 0.000 claims 1
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims 1
229910052759 nickel Inorganic materials 0.000 claims 1
229910052703 rhodium Inorganic materials 0.000 claims 1
239000010948 rhodium Substances 0.000 claims 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
229910052707 ruthenium Inorganic materials 0.000 claims 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
239000007787 solid Substances 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
239000000203 mixture Substances 0.000 description 13
239000003921 oil Substances 0.000 description 13
239000012044 organic layer Substances 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
JHLUHSUKOPRKDY-UHFFFAOYSA-N 1-(2-methoxyethyl)-4-phenylimidazolidin-2-one Chemical compound N1C(=O)N(CCOC)CC1C1=CC=CC=C1 JHLUHSUKOPRKDY-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
239000008096 xylene Substances 0.000 description 4
WDUKOZVBDZRNCC-UHFFFAOYSA-N 1-(2-methoxyethyl)-4-phenylimidazolidine-2-thione Chemical compound N1C(=S)N(CCOC)CC1C1=CC=CC=C1 WDUKOZVBDZRNCC-UHFFFAOYSA-N 0.000 description 3
ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
WZMHXRHBDLIRTR-UHFFFAOYSA-N 3-(2-hydroxyethyl)-5-phenyl-1h-imidazol-2-one Chemical compound N1C(=O)N(CCO)C=C1C1=CC=CC=C1 WZMHXRHBDLIRTR-UHFFFAOYSA-N 0.000 description 2
YXYOJZOKGZFVJY-UHFFFAOYSA-N 3-benzoyl-1-(2-methoxyethyl)-4-phenylimidazol-2-one Chemical compound C=1C=CC=CC=1C(=O)N1C(=O)N(CCOC)C=C1C1=CC=CC=C1 YXYOJZOKGZFVJY-UHFFFAOYSA-N 0.000 description 2
PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WIRUZQNBHNAMAB-UHFFFAOYSA-N benzene;cyclohexane Chemical compound C1CCCCC1.C1=CC=CC=C1 WIRUZQNBHNAMAB-UHFFFAOYSA-N 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 2
150000002169 ethanolamines Chemical class 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000010410 layer Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
238000001665 trituration Methods 0.000 description 2
HCKXIENNWYVMBG-UHFFFAOYSA-N 1-(2-methoxyethyl)-3-(2-methylbenzoyl)-4-phenylimidazol-2-one Chemical compound C=1C=CC=C(C)C=1C(=O)N1C(=O)N(CCOC)C=C1C1=CC=CC=C1 HCKXIENNWYVMBG-UHFFFAOYSA-N 0.000 description 1
IHAYBLBOZGDCME-UHFFFAOYSA-N 1-(2-methoxyethyl)-3-(2-methylbenzoyl)-4-phenylimidazolidin-2-one Chemical compound O=C1N(CCOC)CC(C=2C=CC=CC=2)N1C(=O)C1=CC=CC=C1C IHAYBLBOZGDCME-UHFFFAOYSA-N 0.000 description 1
LSPJMBLAOWKCPK-UHFFFAOYSA-N 1-(2-methoxyethyl)-4-(3-methylphenyl)imidazolidin-2-one Chemical compound N1C(=O)N(CCOC)CC1C1=CC=CC(C)=C1 LSPJMBLAOWKCPK-UHFFFAOYSA-N 0.000 description 1
FJKVAMGLMXDBGJ-UHFFFAOYSA-N 1-(2-methoxyethyl)-4-[4-(trifluoromethyl)phenyl]imidazolidin-2-one Chemical compound N1C(=O)N(CCOC)CC1C1=CC=C(C(F)(F)F)C=C1 FJKVAMGLMXDBGJ-UHFFFAOYSA-N 0.000 description 1
LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
MZNKYQYJLAEUCZ-UHFFFAOYSA-N 2-(2-oxo-4-phenylimidazolidin-1-yl)ethyl 4-methylbenzoate Chemical compound C1=CC(C)=CC=C1C(=O)OCCN1C(=O)NC(C=2C=CC=CC=2)C1 MZNKYQYJLAEUCZ-UHFFFAOYSA-N 0.000 description 1
YSRXTEPZMFRFCO-UHFFFAOYSA-N 2-(2-oxo-5-phenyl-1h-imidazol-3-yl)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCN(C(N1)=O)C=C1C1=CC=CC=C1 YSRXTEPZMFRFCO-UHFFFAOYSA-N 0.000 description 1
GUJVSACUUYJUNG-UHFFFAOYSA-N 2-(5-phenyl-1,2-dihydroimidazol-3-yl)ethyl 4-(trifluoromethyl)benzoate Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)OCCN1C=C(C=2C=CC=CC=2)NC1 GUJVSACUUYJUNG-UHFFFAOYSA-N 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
WZWWEVCLPKAQTA-UHFFFAOYSA-N 2-bromo-1-(2-chlorophenyl)ethanone Chemical compound ClC1=CC=CC=C1C(=O)CBr WZWWEVCLPKAQTA-UHFFFAOYSA-N 0.000 description 1
BFBKUYFMLNOLOQ-UHFFFAOYSA-N 2-butoxyethanamine Chemical compound CCCCOCCN BFBKUYFMLNOLOQ-UHFFFAOYSA-N 0.000 description 1
GUXJXWKCUUWCLX-UHFFFAOYSA-N 2-methyl-2-oxazoline Chemical compound CC1=NCCO1 GUXJXWKCUUWCLX-UHFFFAOYSA-N 0.000 description 1
ZXTHWIZHGLNEPG-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1 ZXTHWIZHGLNEPG-UHFFFAOYSA-N 0.000 description 1
DQGFAMWKZFDSKW-UHFFFAOYSA-N 3-(2,4-dichlorobenzoyl)-1-(2-methoxyethyl)-4-phenylimidazol-2-one Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)N1C(=O)N(CCOC)C=C1C1=CC=CC=C1 DQGFAMWKZFDSKW-UHFFFAOYSA-N 0.000 description 1
YJDRVSJGZCFZTQ-UHFFFAOYSA-N 3-(2-chlorobenzoyl)-1-(2-methoxyethyl)-4-phenylimidazolidin-2-one Chemical compound O=C1N(CCOC)CC(C=2C=CC=CC=2)N1C(=O)C1=CC=CC=C1Cl YJDRVSJGZCFZTQ-UHFFFAOYSA-N 0.000 description 1
ADTDHVCWTLTZMW-UHFFFAOYSA-N 3-(2-hydroxyethyl)-5-phenyl-1h-imidazole-2-thione Chemical compound N1C(=S)N(CCO)C=C1C1=CC=CC=C1 ADTDHVCWTLTZMW-UHFFFAOYSA-N 0.000 description 1
AMJOCQNFFKVXHL-UHFFFAOYSA-N 3-(2-methoxybenzoyl)-1-(2-methoxyethyl)-4-phenylimidazolidin-2-one Chemical compound O=C1N(CCOC)CC(C=2C=CC=CC=2)N1C(=O)C1=CC=CC=C1OC AMJOCQNFFKVXHL-UHFFFAOYSA-N 0.000 description 1
KFEAAJBPOBCQCP-UHFFFAOYSA-N 3-ethenyl-5-phenyl-1h-imidazole-2-thione Chemical compound N1C(=S)N(C=C)C=C1C1=CC=CC=C1 KFEAAJBPOBCQCP-UHFFFAOYSA-N 0.000 description 1
OLYKFGWSRLGXGS-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(2-methoxyethyl)-1h-imidazol-2-one Chemical compound N1C(=O)N(CCOC)C=C1C1=CC=CC=C1Cl OLYKFGWSRLGXGS-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
229940124339 anthelmintic agent Drugs 0.000 description 1
239000000921 anthelmintic agent Substances 0.000 description 1
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
239000002815 homogeneous catalyst Substances 0.000 description 1
238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 description 1
238000006197 hydroboration reaction Methods 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
239000007858 starting material Substances 0.000 description 1
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 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/70—One oxygen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/38—One oxygen atom with acyl radicals or hetero atoms directly attached to ring nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/42—Sulfur atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO771422A 1976-04-26 1977-04-25 Fremgangsm}te for fremstilling av tetramisol, levamisol og derivater derav NO771422L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US68031176A	1976-04-26	1976-04-26
US05/739,924 US4090025A (en)	1976-04-26	1976-11-08	Intermediates for synthesis of tetramisole, levamisole and their derivatives

Publications (1)

Publication Number	Publication Date
NO771422L true NO771422L (no)	1977-10-27

Family

ID=27102431

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO771422A NO771422L (no)	1976-04-26	1977-04-25	Fremgangsm}te for fremstilling av tetramisol, levamisol og derivater derav

Country Status (14)

Country	Link
JP (1)	JPS52142067A (da)
AU (1)	AU2341277A (da)
DD (1)	DD131175A5 (da)
DE (1)	DE2718059A1 (da)
DK (1)	DK181177A (da)
ES (1)	ES458164A1 (da)
FR (1)	FR2370735A1 (da)
GB (2)	GB1579862A (da)
IL (1)	IL51654A0 (da)
IT (1)	IT1086883B (da)
NL (1)	NL7704424A (da)
NO (1)	NO771422L (da)
NZ (1)	NZ183622A (da)
SE (1)	SE7704745L (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL51639A0 (en) *	1976-04-26	1977-05-31	American Cyanamid Co	New synthesis of tetramisole levamisole and their derivatives

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3726894A (en) *	1971-06-24	1973-04-10	American Cyanamid Co	The compound 1-(2-hydroxyethyl)-4-phenyl-2-imidazolidinethione
GB1435900A (en) *	1972-10-04	1976-05-19	Agfa Gevaert	Method for the preparation of planographic printing plates
FR2258379A1 (en) *	1974-01-21	1975-08-18	Aries Robert	Imidazo thiazolidine anthelmintics - prepd from an ethylene thiourea and a haloethanol, halogenation and cyclisation

1977
- 1977-03-14 IL IL51654A patent/IL51654A0/xx unknown
- 1977-03-16 NZ NZ183622A patent/NZ183622A/xx unknown
- 1977-03-17 GB GB3668/79A patent/GB1579862A/en not_active Expired
- 1977-03-17 GB GB11485/77A patent/GB1579861A/en not_active Expired
- 1977-03-18 AU AU23412/77A patent/AU2341277A/en not_active Expired
- 1977-04-07 IT IT48871/77A patent/IT1086883B/it active
- 1977-04-22 NL NL7704424A patent/NL7704424A/xx not_active Application Discontinuation
- 1977-04-22 DE DE19772718059 patent/DE2718059A1/de not_active Withdrawn
- 1977-04-25 DK DK181177A patent/DK181177A/da not_active Application Discontinuation
- 1977-04-25 SE SE7704745A patent/SE7704745L/xx unknown
- 1977-04-25 NO NO771422A patent/NO771422L/no unknown
- 1977-04-26 ES ES458164A patent/ES458164A1/es not_active Expired
- 1977-04-26 DD DD7700198605A patent/DD131175A5/xx unknown
- 1977-04-26 JP JP4745477A patent/JPS52142067A/ja active Pending
- 1977-04-26 FR FR7712567A patent/FR2370735A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
NL7704424A (nl)	1977-10-28
DK181177A (da)	1977-10-27
JPS52142067A (en)	1977-11-26
IT1086883B (it)	1985-05-31
SE7704745L (sv)	1977-10-27
FR2370735A1 (fr)	1978-06-09
IL51654A0 (en)	1977-05-31
GB1579861A (en)	1980-11-26
DD131175A5 (de)	1978-06-07
AU2341277A (en)	1978-09-21
NZ183622A (en)	1980-04-28
GB1579862A (en)	1980-11-26
ES458164A1 (es)	1978-08-16
DE2718059A1 (de)	1977-11-10

Publication	Publication Date	Title
EP1747199B1 (en)	2014-09-17	Pyrrolidin-2-one and piperidin-2-one derivatives as 11-beta hydroxysteroid dehydrogenase inhibitors
NO162977B (no)	1989-12-04	Filt for fremstilling av en vaatpressefilt for en papirmaskin, samt fremgangsmaate ved fremstilling derav.
DE2539452A1 (de)	1976-03-18	1,3,4-trisubstituierte-4-arylpiperidine
WO2010011811A2 (en)	2010-01-28	3-(phenoxyphenylmethyl)pyrrolidine compounds
EP0177960B1 (de)	1991-03-20	Tetrahydronaphtalinderivate, Verfahren und Zwischenprodukte zu deren Herstellung sowie diese enthaltende Arzneimittel
KR850001228B1 (ko)	1985-08-23	치환 인돌린-2-온 유도체의 제조방법
EP0012866B1 (en)	1983-01-19	New 3h-naphtho(1,2-d)imidazoles, processes for preparing them, compounds for use as antiinflammatory and antimicrobial agents and compositions for that use containing them
DE68915310T2 (de)	1994-09-08	Verfahren zur Herstellung von enantiomerischen homogenen Aminopyrrolidinyl-naphthyridin- und Quinoloncarbonsäuren.
US4435417A (en)	1984-03-06	Antiinflammatory 3H-naphtho[1,2-d]imidazoles
NO771422L (no)	1977-10-27	Fremgangsm}te for fremstilling av tetramisol, levamisol og derivater derav
US4090025A (en)	1978-05-16	Intermediates for synthesis of tetramisole, levamisole and their derivatives
US4446148A (en)	1984-05-01	Benzodioxanyl imidazoline compounds, compositions and use
Deshpande et al.	1998	A scalable process for the novel antidepressant ABT-200
US4391978A (en)	1983-07-05	Phenyl-quinolizidines
EP0041630B1 (en)	1985-03-13	New 3h-naphtho(1,2-d)imidazoles, the process for preparing them, the compounds for use as antiinflammatory agents and compositions containing them
US4310672A (en)	1982-01-12	Synthesis of intermediates for tetramisole, levamisole and their derivatives
US4620009A (en)	1986-10-28	Synthesis of intermediates for tetramisole, levamisole and their derivatives
JPH06293731A (ja)	1994-10-21	４−置換プロリン誘導体の中間体
NO771421L (no)	1977-10-27	Fremgangsm}te for fremstilling av tetramisol, levamisol og derivater derav
De Oliveira et al.	2007	Synthesis of pyrrolidine-substituted benzamides via iodocyclization of β-enaminoesters
US4139707A (en)	1979-02-13	Intermediates for synthesis of tetramisole, levamisole and their derivatives
US4370482A (en)	1983-01-25	Synthesis of tetramisole, levamisole and their derivatives
EP0209275B1 (en)	1988-10-19	Benz-trisubstituted 2-aminotetralins
DE2818290A1 (de)	1978-11-09	Neue naphthyridine
SK283177B6 (sk)	2003-03-04	Derivát piperidinylmetyloxazolidinónu, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje