NO771421L - 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: NO771421L
Authority: NO; Norway
Prior art keywords: phenyl; imidazolidone; methoxyethyl; formula; alkyl
Prior art date: 1976-04-26

Application number

NO771421A

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 US05/739,923 external-priority patent/US4087611A/en

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

1977-10-27 Publication of NO771421L publication Critical patent/NO771421L/no

Links

238000000034 method Methods 0.000 title claims abstract description 26
238000002360 preparation method Methods 0.000 title claims abstract description 13
HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 title abstract description 31
229960001614 levamisole Drugs 0.000 title abstract description 30
150000001875 compounds Chemical class 0.000 claims description 48
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 47
239000002904 solvent Substances 0.000 claims description 26
229910052739 hydrogen Inorganic materials 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
-1 alkyl-C^-C^ Chemical group 0.000 claims description 15
239000003054 catalyst Substances 0.000 claims description 15
YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 12
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 claims description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
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
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 7
238000005984 hydrogenation reaction Methods 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
239000011593 sulfur Substances 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
239000004215 Carbon black (E152) Substances 0.000 claims description 5
239000003153 chemical reaction reagent Substances 0.000 claims description 5
150000002431 hydrogen Chemical group 0.000 claims description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
238000010992 reflux Methods 0.000 claims description 5
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 claims description 4
229930195733 hydrocarbon Natural products 0.000 claims description 4
150000002430 hydrocarbons Chemical class 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
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 3
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 3
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 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
150000001450 anions Chemical class 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
239000012458 free base Substances 0.000 claims description 3
150000002576 ketones Chemical class 0.000 claims description 3
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
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 claims description 2
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 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
239000005864 Sulphur Substances 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 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
ATSKSRHMKXVFDQ-UHFFFAOYSA-N 1-(2-methoxyethyl)-4-phenyl-3-[4-(trifluoromethyl)benzoyl]imidazolidin-2-one Chemical compound O=C1N(CCOC)CC(C=2C=CC=CC=2)N1C(=O)C1=CC=C(C(F)(F)F)C=C1 ATSKSRHMKXVFDQ-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
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 claims 1
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 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
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
150000008282 halocarbons Chemical class 0.000 claims 1
125000005059 halophenyl group Chemical group 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
239000007787 solid Substances 0.000 description 23
239000003921 oil Substances 0.000 description 20
239000000203 mixture Substances 0.000 description 17
239000012044 organic layer Substances 0.000 description 16
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
230000000875 corresponding effect Effects 0.000 description 11
239000000706 filtrate Substances 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-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
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 8
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
230000015572 biosynthetic process Effects 0.000 description 4
239000000463 material Substances 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
238000003786 synthesis 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
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 description 3
ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 3
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 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 description 3
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 3
PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
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 description 2
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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
239000012298 atmosphere Substances 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
230000003197 catalytic effect Effects 0.000 description 2
238000010531 catalytic reduction reaction Methods 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
XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 2
QSUDXYGZLAJAQU-QBHQJVBUSA-L cyclooctadiene rhodium chloride dimer Chemical compound [Rh]Cl.[Rh]Cl.C1C\C=C/CCC=C1.C/1C\C=C/CC\C=C\1 QSUDXYGZLAJAQU-QBHQJVBUSA-L 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
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000010410 layer Substances 0.000 description 2
239000012434 nucleophilic reagent Substances 0.000 description 2
239000003579 shift reagent Substances 0.000 description 2
239000000126 substance Substances 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
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
HYHFDALRHXTRHK-UHFFFAOYSA-N 2-(2-oxo-4-phenylimidazolidin-1-yl)ethyl propanoate Chemical compound N1C(=O)N(CCOC(=O)CC)CC1C1=CC=CC=C1 HYHFDALRHXTRHK-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
QASUETYZOSDVCF-UHFFFAOYSA-N 2-(2-oxo-5-phenyl-1h-imidazol-3-yl)ethyl propanoate Chemical compound N1C(=O)N(CCOC(=O)CC)C=C1C1=CC=CC=C1 QASUETYZOSDVCF-UHFFFAOYSA-N 0.000 description 1
GPIZPGLHUHPWMF-UHFFFAOYSA-N 2-(4-phenyl-4,5-dihydroimidazol-1-yl)ethyl 4-methylbenzoate Chemical compound C1=CC(C)=CC=C1C(=O)OCCN1C=NC(C=2C=CC=CC=2)C1 GPIZPGLHUHPWMF-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
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
SOWZXDKYASHVBZ-UHFFFAOYSA-N 3-(2-chlorobenzoyl)-1-(2-methoxyethyl)-4-phenylimidazol-2-one Chemical compound C=1C=CC=C(Cl)C=1C(=O)N1C(=O)N(CCOC)C=C1C1=CC=CC=C1 SOWZXDKYASHVBZ-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
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 description 1
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 description 1
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 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
QTDYPBTYVBRRIB-UHFFFAOYSA-N 5-(2,4-dichlorophenyl)-3-(2-methoxyethyl)-1h-imidazol-2-one Chemical compound N1C(=O)N(CCOC)C=C1C1=CC=C(Cl)C=C1Cl QTDYPBTYVBRRIB-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
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
101100295738 Gallus gallus COR3 gene Proteins 0.000 description 1
FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
239000005456 alcohol based solvent Substances 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000000908 ammonium hydroxide Substances 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
239000003849 aromatic solvent Substances 0.000 description 1
238000011914 asymmetric synthesis Methods 0.000 description 1
WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 1
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000012069 chiral reagent Substances 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
HLFSDGLLUJUHTE-JTQLQIEISA-N dexamisole Chemical compound C1([C@@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-JTQLQIEISA-N 0.000 description 1
238000010586 diagram Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012259 ether extract Substances 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
LNBHUCHAFZUEGJ-UHFFFAOYSA-N europium(3+) Chemical class [Eu+3] LNBHUCHAFZUEGJ-UHFFFAOYSA-N 0.000 description 1
BWIHMSGCCRUUCZ-NCJHBDPTSA-K europium(3+);(1z)-2,2,2-trifluoro-1-(4,7,7-trimethyl-3-oxo-2-bicyclo[2.2.1]heptanylidene)ethanolate Chemical compound [Eu+3].C1CC2(C)C(=O)\C(=C(/[O-])C(F)(F)F)C1C2(C)C.C1CC2(C)C(=O)\C(=C(/[O-])C(F)(F)F)C1C2(C)C.C1CC2(C)C(=O)\C(=C(/[O-])C(F)(F)F)C1C2(C)C BWIHMSGCCRUUCZ-NCJHBDPTSA-K 0.000 description 1
YXJPWWGLCOPUGI-NCJHBDPTSA-N europium;(2z)-4,7,7-trimethyl-2-(2,2,2-trifluoro-1-hydroxyethylidene)bicyclo[2.2.1]heptan-3-one Chemical compound [Eu].C1CC2(C)C(=O)\C(=C(/O)C(F)(F)F)C1C2(C)C.C1CC2(C)C(=O)\C(=C(/O)C(F)(F)F)C1C2(C)C.C1CC2(C)C(=O)\C(=C(/O)C(F)(F)F)C1C2(C)C YXJPWWGLCOPUGI-NCJHBDPTSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 description 1
238000006197 hydroboration reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-O oxonium Chemical compound [OH3+] XLYOFNOQVPJJNP-UHFFFAOYSA-O 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
239000002002 slurry Substances 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
POECFFCNUXZPJT-UHFFFAOYSA-M sodium;carbonic acid;hydrogen carbonate Chemical class [Na+].OC(O)=O.OC([O-])=O POECFFCNUXZPJT-UHFFFAOYSA-M 0.000 description 1
230000003595 spectral effect Effects 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
150000003512 tertiary amines Chemical class 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
- C07D233/04—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
- 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
- C07D233/54—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

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)
Pyrrole Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO771421A 1976-04-26 1977-04-25 Fremgangsm}te for fremstilling av tetramisol, levamisol og derivater derav NO771421L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US68030276A	1976-04-26	1976-04-26
US05/739,923 US4087611A (en)	1976-04-26	1976-11-08	Optically active 1-oxyethyl-4-phenyl-2-imidazolidones

Publications (1)

Publication Number	Publication Date
NO771421L true NO771421L (no)	1977-10-27

Family

ID=27102426

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO771421A NO771421L (no)	1976-04-26	1977-04-25	Fremgangsm}te for fremstilling av tetramisol, levamisol og derivater derav

Country Status (16)

Country	Link
JP (1)	JPS52131579A (it)
AR (1)	AR214311A1 (it)
AU (1)	AU2341177A (it)
DD (1)	DD131170A5 (it)
DE (1)	DE2718058A1 (it)
DK (1)	DK181077A (it)
ES (1)	ES458163A1 (it)
FR (1)	FR2371433A1 (it)
GB (1)	GB1580352A (it)
IL (1)	IL51639A0 (it)
IT (1)	IT1086594B (it)
NL (1)	NL7704251A (it)
NO (1)	NO771421L (it)
NZ (1)	NZ183577A (it)
SE (1)	SE7704744L (it)
SU (1)	SU791231A3 (it)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB0604822D0 (en) *	2006-03-09	2006-04-19	Arakis Ltd	The treatment of inflammatory disorders and pain

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5010106A (it) *	1973-05-24	1975-02-01
JPS5225301B2 (it) *	1973-11-16	1977-07-06
IL51654A0 (en) *	1976-04-26	1977-05-31	American Cyanamid Co	New non-asymmetric synthesis of tetramisole levamisole and their derivatives

1977
- 1977-03-10 IL IL51639A patent/IL51639A0/xx unknown
- 1977-03-11 NZ NZ183577A patent/NZ183577A/xx unknown
- 1977-03-17 GB GB10270/77A patent/GB1580352A/en not_active Expired
- 1977-03-18 AU AU23411/77A patent/AU2341177A/en not_active Expired
- 1977-03-25 AR AR266986A patent/AR214311A1/es active
- 1977-04-18 SU SU772470213A patent/SU791231A3/ru active
- 1977-04-19 NL NL7704251A patent/NL7704251A/xx not_active Application Discontinuation
- 1977-04-20 IT IT49033/77A patent/IT1086594B/it active
- 1977-04-22 DE DE19772718058 patent/DE2718058A1/de not_active Withdrawn
- 1977-04-25 SE SE7704744A patent/SE7704744L/xx unknown
- 1977-04-25 DK DK181077A patent/DK181077A/da not_active Application Discontinuation
- 1977-04-25 NO NO771421A patent/NO771421L/no unknown
- 1977-04-26 JP JP4745577A patent/JPS52131579A/ja active Pending
- 1977-04-26 FR FR7712566A patent/FR2371433A1/fr active Pending
- 1977-04-26 ES ES458163A patent/ES458163A1/es not_active Expired
- 1977-04-26 DD DD7700198606A patent/DD131170A5/xx unknown

Also Published As

Publication number	Publication date
DD131170A5 (de)	1978-06-07
NL7704251A (nl)	1977-10-28
IT1086594B (it)	1985-05-28
GB1580352A (en)	1980-12-03
AU2341177A (en)	1978-09-21
SE7704744L (sv)	1977-10-27
SU791231A3 (ru)	1980-12-23
JPS52131579A (en)	1977-11-04
FR2371433A1 (fr)	1978-06-16
ES458163A1 (es)	1979-06-01
NZ183577A (en)	1980-03-05
IL51639A0 (en)	1977-05-31
DE2718058A1 (de)	1977-11-17
AR214311A1 (es)	1979-05-31
DK181077A (da)	1977-10-27

Publication	Publication Date	Title
SU1544186A3 (ru)	1990-02-15	Способ получени амидов
EP1791821B1 (en)	2013-06-05	Novel imidazolidin-2-one derivatives as selective androgen receptor modulators (sarms)
CA1242193A (en)	1988-09-20	1-benzyl-aminoalkyl-pyrrolidinones and the acid addition salts thereof, processes for preparing them and pharmaceutical compositions
NO320313B1 (no)	2005-11-21	Tienylazolylalkoksyetanaminer, deres fremstilling og deres anvendelse som medikamenter, samt farmasoytisk sammensetning som innbefatter dem
MX2011004996A (es)	2011-05-25	1-(arilsulfonil)-4-(piperazin-1-il)-1h-benzimidazoles como ligandos de 5-hidroxitriptamina-6.
SU1241986A3 (ru)	1986-06-30	Способ получени производных бензамида,их гидрохлоридов или оптических изомеров
CH630383A5 (de)	1982-06-15	Verfahren zur herstellung von cyclischen derivaten von 1,4-benzoxazin und 1,4-benzothiazin.
EP0841330B1 (fr)	2001-06-27	Nouveaux dérivés aminométhyl hétérocycliques, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
DE602006000102T2 (de)	2008-06-26	Indanyl-piperazinderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
US4797496A (en)	1989-01-10	Process for the preparation of pyrrolidone derivatives
NO771421L (no)	1977-10-27	Fremgangsm}te for fremstilling av tetramisol, levamisol og derivater derav
Pallavicini et al.	1994	Synthesis of (−)-and (+)-esermethole via chemical resolution of 1, 3-dimethyl-3-(2-aminoethyl)-5-methoxyoxindole
US6414151B1 (en)	2002-07-02	Process for making 1,3-disubstituted-4-oxocyclic ureas
US4090025A (en)	1978-05-16	Intermediates for synthesis of tetramisole, levamisole and their derivatives
US4087611A (en)	1978-05-02	Optically active 1-oxyethyl-4-phenyl-2-imidazolidones
US6420568B1 (en)	2002-07-16	Process for making 1,3-disubstituted-4-oxocyclic ureas
SU1222191A3 (ru)	1986-03-30	Способ получени соединений гуанидина или их фармакологически совместимых солей
Poindexter et al.	1994	Use of 2-oxazolidinones as latent aziridine equivalents. III. Preparation of N-substituted piperazines
US4370482A (en)	1983-01-25	Synthesis of tetramisole, levamisole and their derivatives
EP0128120A2 (de)	1984-12-12	Trisubstituierte Oxazolidinone
Harnden et al.	1970	Synthesis of compounds with potential central nervous system stimulant activity. II. 5-Spiro-substituted 2-amino-2-oxazolines
US4310672A (en)	1982-01-12	Synthesis of intermediates for tetramisole, levamisole and their derivatives
NO771422L (no)	1977-10-27	Fremgangsm}te for fremstilling av tetramisol, levamisol og derivater derav
US4139707A (en)	1979-02-13	Intermediates for synthesis of tetramisole, levamisole and their derivatives
US4314066A (en)	1982-02-02	Synthesis of tetramisole, levamisole and their derivatives