CA1085859A - Preparation industrielle de pyrrolidones - Google Patents

Preparation industrielle de pyrrolidones

Info

Publication number: CA1085859A
Authority: CA; Canada
Prior art keywords: formula; pyrrolidone; compound; hexen; yield
Prior art date: 1975-06-27
Legal status (The legal status 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 status listed.): Expired

Application number

CA255,666A

Other languages

English (en)

Inventor

Wilhelm Bartmann

Rudolf Kunstmann

Ulrich Lerch

Bernward Scholkens

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hoechst AG

Original Assignee

Hoechst AG

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.)

1975-06-27

Filing date

1976-06-25

Publication date

1980-09-16

1975-06-27 Priority claimed from DE19752528664 external-priority patent/DE2528664A1/de

1975-12-13 Priority claimed from DE19752556326 external-priority patent/DE2556326A1/de

1976-06-25 Application filed by Hoechst AG filed Critical Hoechst AG

1980-09-16 Application granted granted Critical

1980-09-16 Publication of CA1085859A publication Critical patent/CA1085859A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 55
150000004040 pyrrolidinones Chemical class 0.000 title abstract description 9
238000004519 manufacturing process Methods 0.000 title description 4
235000013350 formula milk Nutrition 0.000 claims description 288
150000001875 compounds Chemical class 0.000 claims description 220
-1 aliphatic hydrocarbon radical Chemical class 0.000 claims description 91
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 74
239000002253 acid Substances 0.000 claims description 72
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 62
125000004432 carbon atom Chemical group C* 0.000 claims description 50
239000002585 base Substances 0.000 claims description 35
239000001257 hydrogen Substances 0.000 claims description 35
229910052739 hydrogen Inorganic materials 0.000 claims description 35
125000006239 protecting group Chemical group 0.000 claims description 31
150000002148 esters Chemical class 0.000 claims description 30
229910052757 nitrogen Inorganic materials 0.000 claims description 30
125000004433 nitrogen atom Chemical group N* 0.000 claims description 29
230000000875 corresponding effect Effects 0.000 claims description 28
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 27
150000001450 anions Chemical class 0.000 claims description 27
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 21
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 21
239000000203 mixture Substances 0.000 claims description 21
229910052751 metal Inorganic materials 0.000 claims description 20
239000002184 metal Substances 0.000 claims description 20
238000002360 preparation method Methods 0.000 claims description 18
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 17
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 12
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 11
150000007513 acids Chemical class 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
239000000126 substance Substances 0.000 claims description 10
229930195733 hydrocarbon Natural products 0.000 claims description 9
235000006408 oxalic acid Nutrition 0.000 claims description 9
239000004215 Carbon black (E152) Substances 0.000 claims description 8
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
238000005886 esterification reaction Methods 0.000 claims description 6
125000003158 alcohol group Chemical group 0.000 claims description 5
125000001931 aliphatic group Chemical group 0.000 claims description 5
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
230000032050 esterification Effects 0.000 claims description 5
OEWJGOMAYLEAKO-HYXAFXHYSA-N methyl (z)-7-bromohept-5-enoate Chemical compound COC(=O)CCC\C=C/CBr OEWJGOMAYLEAKO-HYXAFXHYSA-N 0.000 claims description 5
229920006395 saturated elastomer Polymers 0.000 claims description 5
125000005108 alkenylthio group Chemical group 0.000 claims description 4
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 claims description 4
230000001681 protective effect Effects 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 claims description 4
125000003302 alkenyloxy group Chemical group 0.000 claims description 3
150000001350 alkyl halides Chemical class 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
LQZCYXCHWNQBKX-UHFFFAOYSA-N 1-dimethoxyphosphorylheptan-2-one Chemical compound CCCCCC(=O)CP(=O)(OC)OC LQZCYXCHWNQBKX-UHFFFAOYSA-N 0.000 claims description 2
MLOSJPZSZWUDSK-UHFFFAOYSA-N 4-carboxybutyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC(=O)O)C1=CC=CC=C1 MLOSJPZSZWUDSK-UHFFFAOYSA-N 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
JLGWTGKOSOABRI-UHFFFAOYSA-N B.[Zn] Chemical compound B.[Zn] JLGWTGKOSOABRI-UHFFFAOYSA-N 0.000 claims 6
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims 4
229910001413 alkali metal ion Inorganic materials 0.000 claims 3
HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical group O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 claims 2
LXMQZGGLHVSEBA-UHFFFAOYSA-N chromium;trihydrate Chemical compound O.O.O.[Cr] LXMQZGGLHVSEBA-UHFFFAOYSA-N 0.000 claims 2
150000004702 methyl esters Chemical class 0.000 claims 2
238000010534 nucleophilic substitution reaction Methods 0.000 claims 2
150000003254 radicals Chemical class 0.000 claims 2
MBGWNNJXMYHKQO-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3-[3-(trifluoromethyl)phenoxy]propan-2-one Chemical compound COP(=O)(OC)CC(=O)COC1=CC=CC(C(F)(F)F)=C1 MBGWNNJXMYHKQO-UHFFFAOYSA-N 0.000 claims 1
DVIPKNLRDXLFNP-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3-thiophen-3-yloxypropan-2-one Chemical compound COP(=O)(OC)CC(=O)COC=1C=CSC=1 DVIPKNLRDXLFNP-UHFFFAOYSA-N 0.000 claims 1
NFPZXDGXZCMULE-UHFFFAOYSA-N 4-cyclopentyl-1-dimethoxyphosphoryl-3,3-dimethylbutan-2-one Chemical compound COP(OC)(=O)CC(C(CC1CCCC1)(C)C)=O NFPZXDGXZCMULE-UHFFFAOYSA-N 0.000 claims 1
PYBYLIYKZRCVBI-XQRVVYSFSA-N ethyl (z)-7-bromohept-5-enoate Chemical compound CCOC(=O)CCC\C=C/CBr PYBYLIYKZRCVBI-XQRVVYSFSA-N 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 6
150000003180 prostaglandins Chemical class 0.000 abstract description 6
230000003276 anti-hypertensive effect Effects 0.000 abstract description 5
229940094443 oxytocics prostaglandins Drugs 0.000 abstract description 5
230000003033 spasmogenic effect Effects 0.000 abstract description 4
210000004051 gastric juice Anatomy 0.000 abstract description 3
230000028327 secretion Effects 0.000 abstract description 3
239000000812 cholinergic antagonist Substances 0.000 abstract description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 108
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 102
239000000047 product Substances 0.000 description 95
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
238000006243 chemical reaction Methods 0.000 description 63
238000004587 chromatography analysis Methods 0.000 description 53
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
235000019441 ethanol Nutrition 0.000 description 44
235000019439 ethyl acetate Nutrition 0.000 description 33
239000000243 solution Substances 0.000 description 30
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
239000002904 solvent Substances 0.000 description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
150000001299 aldehydes Chemical class 0.000 description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
229960004756 ethanol Drugs 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
238000005804 alkylation reaction Methods 0.000 description 16
239000000741 silica gel Substances 0.000 description 15
229910002027 silica gel Inorganic materials 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
229960000583 acetic acid Drugs 0.000 description 12
230000029936 alkylation Effects 0.000 description 12
229910052799 carbon Inorganic materials 0.000 description 12
150000002431 hydrogen Chemical class 0.000 description 11
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 11
230000003647 oxidation Effects 0.000 description 11
238000007254 oxidation reaction Methods 0.000 description 11
150000003839 salts Chemical class 0.000 description 11
238000003756 stirring Methods 0.000 description 11
150000002170 ethers Chemical class 0.000 description 10
229940052303 ethers for general anesthesia Drugs 0.000 description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
150000001298 alcohols Chemical class 0.000 description 9
125000003118 aryl group Chemical group 0.000 description 9
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 9
239000012362 glacial acetic acid Substances 0.000 description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
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 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
229960001701 chloroform Drugs 0.000 description 8
229960004132 diethyl ether Drugs 0.000 description 8
239000003480 eluent Substances 0.000 description 8
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
229910052801 chlorine Inorganic materials 0.000 description 7
IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
229940073584 methylene chloride Drugs 0.000 description 7
238000000746 purification Methods 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
239000011734 sodium Substances 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
125000003342 alkenyl group Chemical group 0.000 description 6
125000004429 atom Chemical group 0.000 description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
125000001309 chloro group Chemical group Cl* 0.000 description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
150000004678 hydrides Chemical class 0.000 description 5
229910052740 iodine Inorganic materials 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000007921 spray Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 4
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
238000006052 Horner reaction Methods 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
239000003377 acid catalyst Substances 0.000 description 4
230000002152 alkylating effect Effects 0.000 description 4
150000003863 ammonium salts Chemical class 0.000 description 4
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
239000000499 gel Substances 0.000 description 4
229910052744 lithium Inorganic materials 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
150000002902 organometallic compounds Chemical class 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
XBGYMVTXOUKXLG-UHFFFAOYSA-N 5-oxopyrrolidine-2-carbaldehyde Chemical compound O=CC1CCC(=O)N1 XBGYMVTXOUKXLG-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
241000542311 Ozonium Species 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 3
230000001476 alcoholic effect Effects 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
238000009835 boiling Methods 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
230000003182 bronchodilatating effect Effects 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
150000002084 enol ethers Chemical class 0.000 description 3
230000007717 exclusion Effects 0.000 description 3
125000001153 fluoro group Chemical group F* 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
239000011707 mineral Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
SGEUYXUPUOLFHQ-PLNGDYQASA-N (z)-1-bromohex-2-ene Chemical compound CCC\C=C/CBr SGEUYXUPUOLFHQ-PLNGDYQASA-N 0.000 description 2
VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical class OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 2
YOWQWFMSQCOSBA-UHFFFAOYSA-N 2-methoxypropene Chemical compound COC(C)=C YOWQWFMSQCOSBA-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
229910015900 BF3 Inorganic materials 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
125000006519 CCH3 Chemical group 0.000 description 2
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 2
241000700199 Cavia porcellus Species 0.000 description 2
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
GQWNECFJGBQMBO-UHFFFAOYSA-N Molindone hydrochloride Chemical compound Cl.O=C1C=2C(CC)=C(C)NC=2CCC1CN1CCOCC1 GQWNECFJGBQMBO-UHFFFAOYSA-N 0.000 description 2
101100305983 Mus musculus Rom1 gene Proteins 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
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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
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239000004220 glutamic acid Substances 0.000 description 1
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QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 1
XLXSAKCOAKORKW-AQJXLSMYSA-N gonadorelin Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)NCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 XLXSAKCOAKORKW-AQJXLSMYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
RYPKRALMXUUNKS-UHFFFAOYSA-N hex-2-ene Chemical compound CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
125000001145 hydrido group Chemical group *[H] 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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239000013067 intermediate product Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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150000002576 ketones Chemical class 0.000 description 1
150000003951 lactams Chemical class 0.000 description 1
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239000007788 liquid Substances 0.000 description 1
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
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239000011777 magnesium Substances 0.000 description 1
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239000002609 medium Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
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OEWJGOMAYLEAKO-HWKANZROSA-N methyl (e)-7-bromohept-5-enoate Chemical compound COC(=O)CCC\C=C\CBr OEWJGOMAYLEAKO-HWKANZROSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
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239000002674 ointment Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229960003243 phenformin Drugs 0.000 description 1
ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
239000002089 prostaglandin antagonist Substances 0.000 description 1
WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 description 1
238000011403 purification operation Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
229910001925 ruthenium oxide Inorganic materials 0.000 description 1
WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
230000002048 spasmolytic effect Effects 0.000 description 1
241000894007 species Species 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
239000004094 surface-active agent 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
108010063973 teneurin-1 Proteins 0.000 description 1
MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229960004418 trolamine Drugs 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
229940116269 uric acid Drugs 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Landscapes

Pyrrole Compounds (AREA)

CA255,666A 1975-06-27 1976-06-25 Preparation industrielle de pyrrolidones Expired CA1085859A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DEP2528664.0		1975-06-27
DE19752528664 DE2528664A1 (de)	1975-06-27	1975-06-27	Pyrrolidone und verfahren zu ihrer herstellung
DE19752556326 DE2556326A1 (de)	1975-12-13	1975-12-13	Neue pyrrolidone und verfahren zu ihrer herstellung
DEP2556326.2		1975-12-13

Publications (1)

Publication Number	Publication Date
CA1085859A true CA1085859A (fr)	1980-09-16

Family

ID=25769078

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA255,666A Expired CA1085859A (fr)	1975-06-27	1976-06-25	Preparation industrielle de pyrrolidones

Country Status (1)

Country	Link
CA (1)	CA1085859A (fr)

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US9180116B2 (en)	2012-07-19	2015-11-10	Cayman Chemical Company, Inc.	Difluorolactam compounds as EP4 receptor-selective agonists for use in the treatment of EP4-mediated diseases and conditions
US9676712B2 (en)	2013-03-15	2017-06-13	Cayman Chemical Company, Inc.	Lactam compounds as EP4 receptor-selective agonists for use in the treatment of EP4-mediated diseases and conditions
US9688627B2 (en)	2013-03-15	2017-06-27	Cayman Chemical Company, Inc.	Lactam compounds as EP4 receptor-selective agonists for use in the treatment of EP4-mediated diseases and conditions
US9914725B2 (en)	2013-03-15	2018-03-13	Cayman Chemical Company, Inc.	Methods of synthesizing a difluorolactam analog
US10729810B2 (en)	2013-07-19	2020-08-04	Cayman Chemical Company, Inc	Methods, systems, and compositions for promoting bone growth

1976
- 1976-06-25 CA CA255,666A patent/CA1085859A/fr not_active Expired

Cited By (12)

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Publication number	Priority date	Publication date	Assignee	Title
US9180116B2 (en)	2012-07-19	2015-11-10	Cayman Chemical Company, Inc.	Difluorolactam compounds as EP4 receptor-selective agonists for use in the treatment of EP4-mediated diseases and conditions
US9440919B2 (en)	2012-07-19	2016-09-13	Cayman Chemical Company, Inc.	Difluorolactam compositions for EP4-mediated osteo related diseases and conditions
US9487478B2 (en)	2012-07-19	2016-11-08	Cayman Chemical Company, Inc.	Difluorolactam compounds as EP4 receptor-selective agonists for use in the treatment of EP4-mediated diseases and conditions
US9701630B2 (en)	2012-07-19	2017-07-11	Cayman Chemical Company, Inc.	Difluorolactam compositions for EP4-mediated osteo related diseases and conditions
US10556862B2 (en)	2012-07-19	2020-02-11	Cayman Chemical Company, Inc.	Difluorolactam compounds as EP4 receptor-selective agonists for use in the treatment of EP4-mediated diseases and conditions
US11066361B2 (en)	2012-07-19	2021-07-20	Cayman Chemical Company, Inc.	Difluorolactam compounds as EP4 receptor-selective agonists for use in the treatment of EP4-mediated diseases and conditions
US11884624B2 (en)	2012-07-19	2024-01-30	Cayman Chemical Company, Inc.	Difluorolactam compounds as EP4 receptor-selective agonists for use in the treatment of EP4-mediated diseases and conditions
US9676712B2 (en)	2013-03-15	2017-06-13	Cayman Chemical Company, Inc.	Lactam compounds as EP4 receptor-selective agonists for use in the treatment of EP4-mediated diseases and conditions
US9688627B2 (en)	2013-03-15	2017-06-27	Cayman Chemical Company, Inc.	Lactam compounds as EP4 receptor-selective agonists for use in the treatment of EP4-mediated diseases and conditions
US9914725B2 (en)	2013-03-15	2018-03-13	Cayman Chemical Company, Inc.	Methods of synthesizing a difluorolactam analog
US11345690B2 (en)	2013-03-15	2022-05-31	Cayman Chemical Company, Inc.	Methods of synthesizing a difluorolactam analog
US10729810B2 (en)	2013-07-19	2020-08-04	Cayman Chemical Company, Inc	Methods, systems, and compositions for promoting bone growth

Legal Events

Date	Code	Title	Description
1997-09-16	MKEX	Expiry

Publication	Publication Date	Title
US3975399A (en)	1976-08-17	1,5-Disubstituted-2-pyrrolidinones, -3-pyrrolin-2-ones, and -4-pyrrolin-2-ones
IT8922768A1 (it)	1991-06-21	Composti attivi come inibitori dell'enzima hmg-coa reduttasi
FI63221C (fi)	1983-05-10	Prostansyraderivat foer anvaendning saosom antikonceptionella medel eller foer icke-terapeutisk kontroll av husdjurens oestriska cykel
CA1060888A (fr)	1979-08-21	Derives du cyclopentane
CH623809A5 (en)	1981-06-30	Process for the preparation of pyrrolidones
CA1085859A (fr)	1980-09-16	Preparation industrielle de pyrrolidones
Paquette et al.	1982	An effective approach to stereocontrolled lactone annulation. Application to the total synthesis of pentalenolactone E methyl ester and a partial elaboration of quadrone
CA1254895A (fr)	1989-05-30	.beta.-CARBOLINES, METHODE DE PREPARATION ET UTILISATION COMME AGENTS MEDICINAUX
DE2348632A1 (de)	1974-04-11	Prostansaeurederivate
US3881017A (en)	1975-04-29	9-Thiaprostaglandin compositions
US4077979A (en)	1978-03-07	9-Thiaprostaglandins
FI95252C (fi)	1996-01-10	Menetelmä lääkeaineina käyttökelpoisten dihydrotianaftaleeniyhdisteiden valmistamiseksi
HU190007B (en)	1986-08-28	Process for producing new aromatic prostacylin analogues
CA1252461A (fr)	1989-04-11	Derives de bicyclo-octane, leur preparation et leur emploi
US4262008A (en)	1981-04-14	2,4-Disubstituted 5-oxo-5H-hexahydrofuro[3,2b]pyrroles
CA1072108A (fr)	1980-02-19	Les pyrrolidones et procede pour leur fabrication
US4079145A (en)	1978-03-14	Certain pyrrolidone derivatives and pharmaceutical use thereof
US4312882A (en)	1982-01-26	Thienyoxy and furyl containing analogs of prostacyclin and their use as medicaments
US4871764A (en)	1989-10-03	12-Halogenated forskolin derivatives
US4515946A (en)	1985-05-07	6,11-Dihydro-11-oxo-dibenz-[b,e]oxepin derivatives
EP0593537A1 (fr)	1994-04-27	Antagonistes du facteur d'activation de plaquettes (paf) d'acetal d'ether cyclique
Metz et al.	1994	Claisen rearrangement of N-silyl ketene N, O-acetals generated from allyl N-phenylimidates
CA1095522A (fr)	1981-02-10	Traduction non-disponible
US5559133A (en)	1996-09-24	Orally active antiviral compounds
IE52349B1 (en)	1987-09-16	Alpha chain dienic prostanoic acid derivatives