NO860972L - Fremgangsmaate for fremstilling av guanidiner slik som linoglirid og fremgangsmaate for fremstilling av mellomprodukter. - Google Patents

Fremgangsmaate for fremstilling av guanidiner slik som linoglirid og fremgangsmaate for fremstilling av mellomprodukter.

Info

Publication number: NO860972L
Authority: NO; Norway
Prior art keywords: phenyl; formula; phenyl substituted; temperature; hydrogen peroxide
Prior art date: 1985-03-15

Application number

NO860972A

Other languages

English (en)

Norwegian (no)

Inventor

Cynthia Anne Maryanoff

James Nelson Plampin

Robin Cosgrove Stanzione

Original Assignee

Mcneilab Inc

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.)

1985-03-15

Filing date

1986-03-14

Publication date

1986-09-16

1986-03-14 Application filed by Mcneilab Inc filed Critical Mcneilab Inc

1986-09-16 Publication of NO860972L publication Critical patent/NO860972L/no

Links

238000000034 method Methods 0.000 title claims description 23
OPPLDIXFHYTSSR-GLECISQGSA-N (ne)-n-(1-methylpyrrolidin-2-ylidene)-n'-phenylmorpholine-4-carboximidamide Chemical compound CN1CCC\C1=N/C(N1CCOCC1)=NC1=CC=CC=C1 OPPLDIXFHYTSSR-GLECISQGSA-N 0.000 title description 5
239000000543 intermediate Substances 0.000 title description 4
229950004872 linogliride Drugs 0.000 title description 4
150000002357 guanidines Chemical class 0.000 title description 3
238000004519 manufacturing process Methods 0.000 title description 3
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 45
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 40
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
-1 methylenedioxy phenyl Chemical group 0.000 claims description 27
239000003054 catalyst Substances 0.000 claims description 13
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 11
229910052750 molybdenum Inorganic materials 0.000 claims description 11
239000011733 molybdenum Substances 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 8
230000015572 biosynthetic process Effects 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
230000003647 oxidation Effects 0.000 claims description 6
238000007254 oxidation reaction Methods 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
238000003786 synthesis reaction Methods 0.000 claims description 6
125000001153 fluoro group Chemical group F* 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
230000008569 process Effects 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000005236 alkanoylamino group Chemical group 0.000 claims description 3
150000001450 anions Chemical class 0.000 claims description 3
125000001589 carboacyl group Chemical group 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical group [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 claims description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 3
239000002253 acid Substances 0.000 claims 3
230000001590 oxidative effect Effects 0.000 claims 2
150000002500 ions Chemical class 0.000 claims 1
239000011541 reaction mixture Substances 0.000 description 38
238000006243 chemical reaction Methods 0.000 description 37
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
239000000047 product Substances 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
239000007787 solid Substances 0.000 description 22
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 20
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
238000007792 addition Methods 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
150000003839 salts Chemical class 0.000 description 9
239000000460 chlorine Substances 0.000 description 8
238000001816 cooling Methods 0.000 description 8
239000012065 filter cake Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 6
FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical compound NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 description 6
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 6
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
239000005457 ice water Substances 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
150000002978 peroxides Chemical class 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000001530 fumaric acid Substances 0.000 description 4
RWVGQQGBQSJDQV-UHFFFAOYSA-M sodium;3-[[4-[(e)-[4-(4-ethoxyanilino)phenyl]-[4-[ethyl-[(3-sulfonatophenyl)methyl]azaniumylidene]-2-methylcyclohexa-2,5-dien-1-ylidene]methyl]-n-ethyl-3-methylanilino]methyl]benzenesulfonate Chemical compound [Na+].C1=CC(OCC)=CC=C1NC1=CC=C(C(=C2C(=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C)C=2C(=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C)C=C1 RWVGQQGBQSJDQV-UHFFFAOYSA-M 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
239000008096 xylene Substances 0.000 description 4
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
229910004373 HOAc Inorganic materials 0.000 description 3
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
MIJRUQYZDSEMBD-UHFFFAOYSA-N acetic acid;morpholine Chemical compound CC(O)=O.C1COCCN1 MIJRUQYZDSEMBD-UHFFFAOYSA-N 0.000 description 3
150000003841 chloride salts Chemical class 0.000 description 3
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 3
238000001914 filtration Methods 0.000 description 3
150000003951 lactams Chemical class 0.000 description 3
125000005528 methosulfate group Chemical class 0.000 description 3
239000000203 mixture Substances 0.000 description 3
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000376 reactant Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000002002 slurry Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
239000003472 antidiabetic agent Substances 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
ZSAMTXUUUFXIII-CZKNSKRSSA-N chembl2106766 Chemical compound OC(=O)\C=C\C(O)=O.CN1CCC\C1=N/C(/N1CCOCC1)=N/C1=CC=CC=C1 ZSAMTXUUUFXIII-CZKNSKRSSA-N 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000006184 cosolvent Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
150000004683 dihydrates Chemical class 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 2
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000002243 precursor Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000007858 starting material Substances 0.000 description 2
150000003460 sulfonic acids Chemical class 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
BRWKXKNZRVALNZ-UHFFFAOYSA-N (4-fluorophenyl)thiourea Chemical compound NC(=S)NC1=CC=C(F)C=C1 BRWKXKNZRVALNZ-UHFFFAOYSA-N 0.000 description 1
ZSAMTXUUUFXIII-WLHGVMLRSA-N (e)-but-2-enedioic acid;n-(1-methylpyrrolidin-2-ylidene)-n'-phenylmorpholine-4-carboximidamide Chemical compound OC(=O)\C=C\C(O)=O.CN1CCCC1=NC(N1CCOCC1)=NC1=CC=CC=C1 ZSAMTXUUUFXIII-WLHGVMLRSA-N 0.000 description 1
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
OQILOJRSIWGQSM-UHFFFAOYSA-N 1-methylpyrrolidine-2-thione Chemical compound CN1CCCC1=S OQILOJRSIWGQSM-UHFFFAOYSA-N 0.000 description 1
QWMFKVNJIYNWII-UHFFFAOYSA-N 5-bromo-2-(2,5-dimethylpyrrol-1-yl)pyridine Chemical compound CC1=CC=C(C)N1C1=CC=C(Br)C=N1 QWMFKVNJIYNWII-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
229910004619 Na2MoO4 Inorganic materials 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
241000220317 Rosa Species 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000009471 action Effects 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
150000001356 alkyl thiols Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000003178 anti-diabetic effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000002585 base Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
238000009835 boiling Methods 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
244000309464 bull Species 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
230000008859 change Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000007710 freezing Methods 0.000 description 1
230000008014 freezing Effects 0.000 description 1
150000005826 halohydrocarbons Chemical class 0.000 description 1
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
150000004680 hydrogen peroxides Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
229960005181 morphine Drugs 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
MCQDWRJORJMTCH-UHFFFAOYSA-N n'-phenylmorpholine-4-carboximidamide Chemical compound C1COCCN1C(N)=NC1=CC=CC=C1 MCQDWRJORJMTCH-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
ACLZYRNSDLQOIA-UHFFFAOYSA-N o-tolylthiourea Chemical compound CC1=CC=CC=C1NC(N)=S ACLZYRNSDLQOIA-UHFFFAOYSA-N 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000011684 sodium molybdate Substances 0.000 description 1
235000015393 sodium molybdate Nutrition 0.000 description 1
TVXXNOYZHKPKGW-UHFFFAOYSA-N sodium molybdate (anhydrous) Chemical compound [Na+].[Na+].[O-][Mo]([O-])(=O)=O TVXXNOYZHKPKGW-UHFFFAOYSA-N 0.000 description 1
239000012453 solvate Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
150000003571 thiolactams Chemical class 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten 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
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/14—Compounds containing a carbon atom having four bonds to hetero atoms with a double bond to one hetero atom and at least one bond to a sulfur atom further doubly-bound to oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrrole Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NO860972A 1985-03-15 1986-03-14 Fremgangsmaate for fremstilling av guanidiner slik som linoglirid og fremgangsmaate for fremstilling av mellomprodukter. NO860972L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/711,948 US4656270A (en)	1985-03-15	1985-03-15	Process for producing guanidines such as linogliride

Publications (1)

Publication Number	Publication Date
NO860972L true NO860972L (no)	1986-09-16

Family

ID=24860160

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO860972A NO860972L (no)	1985-03-15	1986-03-14	Fremgangsmaate for fremstilling av guanidiner slik som linoglirid og fremgangsmaate for fremstilling av mellomprodukter.

Country Status (14)

Country	Link
US (1)	US4656270A (xx)
EP (1)	EP0195620A3 (xx)
JP (1)	JPS61263957A (xx)
KR (1)	KR860007211A (xx)
CN (1)	CN86102431A (xx)
AU (1)	AU5475686A (xx)
DK (1)	DK121386A (xx)
ES (1)	ES8704916A1 (xx)
FI (1)	FI861073A (xx)
GR (1)	GR860688B (xx)
HU (1)	HU194815B (xx)
IL (1)	IL78156A0 (xx)
NO (1)	NO860972L (xx)
ZA (1)	ZA861929B (xx)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5948939A (en) *	1986-09-10	1999-09-07	Syntex (U.S.A.) Inc.	Selective amidination of diamines
GB8903592D0 (en) *	1989-02-16	1989-04-05	Boots Co Plc	Therapeutic agents
IN172842B (xx) *	1990-05-17	1993-12-11	Boots Pharmaceuticals Limited
DE69309644T2 (de) *	1992-06-10	1997-07-24	Mitsubishi Gas Chemical Co., Inc., Tokio/Tokyo	Verfahren zur herstellung von thioharnstoffdioxid und das bleichen von papierbrei mit so hergestelltem thioharnstoffdioxid

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1587258A (en) *	1977-06-17	1981-04-01	Gea As	Production of substituted guanidines
US4210658A (en) *	1977-09-08	1980-07-01	Smith Kline & French Laboratories Limited	Amidinosulphonic acid derivatives
US4381395A (en) *	1981-04-03	1983-04-26	Sk & F Lab Co.	Process for preparing an imidazole derivative

1985
- 1985-03-15 US US06/711,948 patent/US4656270A/en not_active Expired - Lifetime
1986
- 1986-03-12 GR GR860688A patent/GR860688B/el unknown
- 1986-03-13 ES ES552981A patent/ES8704916A1/es not_active Expired
- 1986-03-14 KR KR1019860001852A patent/KR860007211A/ko not_active Application Discontinuation
- 1986-03-14 DK DK121386A patent/DK121386A/da not_active Application Discontinuation
- 1986-03-14 EP EP86301893A patent/EP0195620A3/en not_active Withdrawn
- 1986-03-14 ZA ZA861929A patent/ZA861929B/xx unknown
- 1986-03-14 FI FI861073A patent/FI861073A/fi not_active IP Right Cessation
- 1986-03-14 JP JP61055137A patent/JPS61263957A/ja active Pending
- 1986-03-14 IL IL78156A patent/IL78156A0/xx unknown
- 1986-03-14 HU HU861073A patent/HU194815B/hu unknown
- 1986-03-14 NO NO860972A patent/NO860972L/no unknown
- 1986-03-14 AU AU54756/86A patent/AU5475686A/en not_active Abandoned
- 1986-03-15 CN CN198686102431A patent/CN86102431A/zh active Pending

Also Published As

Publication number	Publication date
US4656270A (en)	1987-04-07
KR860007211A (ko)	1986-10-08
GR860688B (en)	1986-07-11
ES552981A0 (es)	1987-04-16
FI861073A (fi)	1986-09-16
DK121386A (da)	1986-09-16
JPS61263957A (ja)	1986-11-21
HU194815B (en)	1988-03-28
EP0195620A2 (en)	1986-09-24
AU5475686A (en)	1986-09-18
IL78156A0 (en)	1986-07-31
ZA861929B (en)	1987-10-28
DK121386D0 (da)	1986-03-14
ES8704916A1 (es)	1987-04-16
FI861073A0 (fi)	1986-03-14
EP0195620A3 (en)	1987-08-19
CN86102431A (zh)	1987-07-01
HUT40621A (en)	1987-01-28

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