CA1268472A - Intermediaires pour la preparation de derives de pyrrolidine - Google Patents

Intermediaires pour la preparation de derives de pyrrolidine

Info

Publication number: CA1268472A
Authority: CA; Canada
Prior art keywords: hydrogen; bromo; ethyl; chloro; compound
Prior art date: 1984-04-02
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 - Fee Related

Application number

CA000555347A

Other languages

English (en)

Inventor

Ugo Pfeiffer

Mario Pinza

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.)

ISF SpA

Original Assignee

ISF SpA

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.)

1984-04-02

Filing date

1987-12-23

Publication date

1990-05-01

1984-04-02 Priority claimed from IT20358/84A external-priority patent/IT1173768B/it

1987-12-23 Application filed by ISF SpA filed Critical ISF SpA

1987-12-23 Priority to CA000555347A priority Critical patent/CA1268472A/fr

1990-05-01 Application granted granted Critical

1990-05-01 Publication of CA1268472A publication Critical patent/CA1268472A/fr

2007-05-01 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims description 5
239000000543 intermediate Substances 0.000 title abstract description 6
150000003235 pyrrolidines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 30
238000000034 method Methods 0.000 claims abstract description 18
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
239000001257 hydrogen Substances 0.000 claims abstract description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
125000006239 protecting group Chemical group 0.000 claims abstract description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
239000002904 solvent Substances 0.000 claims description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 13
230000002378 acidificating effect Effects 0.000 claims description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
125000001246 bromo group Chemical group Br* 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
239000012279 sodium borohydride Substances 0.000 claims description 5
229910000033 sodium borohydride Inorganic materials 0.000 claims description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
CQPVELBRIJTJPV-UHFFFAOYSA-N ethyl 2-[(4-bromo-3-hydroxybutanoyl)amino]acetate Chemical compound CCOC(=O)CNC(=O)CC(O)CBr CQPVELBRIJTJPV-UHFFFAOYSA-N 0.000 claims description 4
150000004678 hydrides Chemical class 0.000 claims description 4
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 3
AIWQHCBDTMNERH-UHFFFAOYSA-N ethyl 2-[(4-chloro-3-hydroxybutanoyl)amino]acetate Chemical compound CCOC(=O)CNC(=O)CC(O)CCl AIWQHCBDTMNERH-UHFFFAOYSA-N 0.000 claims description 3
YWKUVMANUZLOAG-UHFFFAOYSA-N ethyl 2-[[4-chloro-3-(oxan-2-yloxy)butanoyl]amino]acetate Chemical compound CCOC(=O)CNC(=O)CC(CCl)OC1CCCCO1 YWKUVMANUZLOAG-UHFFFAOYSA-N 0.000 claims description 3
125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
PGRQQCJWKVFRDR-UHFFFAOYSA-N ethyl 2-[[4-bromo-3-(oxan-2-yloxy)butanoyl]amino]acetate Chemical compound CCOC(=O)CNC(=O)CC(CBr)OC1CCCCO1 PGRQQCJWKVFRDR-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 abstract description 3
241001465754 Metazoa Species 0.000 abstract description 2
230000003920 cognitive function Effects 0.000 abstract description 2
230000007170 pathology Effects 0.000 abstract description 2
230000000506 psychotropic effect Effects 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 32
239000000243 solution Substances 0.000 description 22
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
229940073584 methylene chloride Drugs 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000000377 silicon dioxide Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
125000000217 alkyl group Chemical group 0.000 description 8
239000003921 oil Substances 0.000 description 8
239000000460 chlorine Substances 0.000 description 7
239000000203 mixture Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000000843 powder Substances 0.000 description 6
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 5
239000003480 eluent Substances 0.000 description 5
IHLAQQPQKRMGSS-UHFFFAOYSA-N oxiracetam Chemical compound NC(=O)CN1CC(O)CC1=O IHLAQQPQKRMGSS-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
239000003377 acid catalyst Substances 0.000 description 4
-1 alkyl 4-hydroxy-2-oxo-1-pyrrolidineacetates Chemical class 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical group C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
239000012267 brine Substances 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
229910052801 chlorine Inorganic materials 0.000 description 3
230000000269 nucleophilic effect Effects 0.000 description 3
229960001227 oxiracetam Drugs 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical compound [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 description 2
WSHVQVCBPLNREW-UHFFFAOYSA-N 4-chloro-3-oxobutanoyl chloride Chemical compound ClCC(=O)CC(Cl)=O WSHVQVCBPLNREW-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
239000004471 Glycine Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
AAHZBXZJLKWBJD-UHFFFAOYSA-N ethyl 2-[4-(oxan-2-yl)-2-oxopyrrolidin-1-yl]acetate Chemical compound C1C(=O)N(CC(=O)OCC)CC1C1OCCCC1 AAHZBXZJLKWBJD-UHFFFAOYSA-N 0.000 description 2
NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
COQRGFWWJBEXRC-UHFFFAOYSA-N hydron;methyl 2-aminoacetate;chloride Chemical compound Cl.COC(=O)CN COQRGFWWJBEXRC-UHFFFAOYSA-N 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000001117 sulphuric acid Substances 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
KNDAEDDIIQYRHY-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(piperazin-1-ylmethyl)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CN1CCNCC1 KNDAEDDIIQYRHY-UHFFFAOYSA-N 0.000 description 1
KXVSPXCGTNISAP-UHFFFAOYSA-N 4-bromo-3-oxobutanoyl bromide Chemical compound BrCC(=O)CC(Br)=O KXVSPXCGTNISAP-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229960002298 aminohydroxybutyric acid Drugs 0.000 description 1
238000007098 aminolysis reaction Methods 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
YDBONCLBTWFUPF-UHFFFAOYSA-N ethyl 2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetate Chemical compound CCOC(=O)CN1CC(O)CC1=O YDBONCLBTWFUPF-UHFFFAOYSA-N 0.000 description 1
BGCUVXVHFRMANM-UHFFFAOYSA-N ethyl 2-[(4-chloro-3-oxobutanoyl)amino]acetate Chemical compound CCOC(=O)CNC(=O)CC(=O)CCl BGCUVXVHFRMANM-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
YQGDEPYYFWUPGO-UHFFFAOYSA-N gamma-amino-beta-hydroxybutyric acid Chemical compound [NH3+]CC(O)CC([O-])=O YQGDEPYYFWUPGO-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 1
150000002332 glycine derivatives Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000011872 intimate mixture Substances 0.000 description 1
230000007775 late Effects 0.000 description 1
YLSQKWDIBHDXNA-UHFFFAOYSA-N methyl 2-[(4-bromo-3-hydroxybutanoyl)amino]acetate Chemical compound COC(=O)CNC(=O)CC(O)CBr YLSQKWDIBHDXNA-UHFFFAOYSA-N 0.000 description 1
KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
150000004040 pyrrolidinones Chemical class 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 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

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Pyrrole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA000555347A 1984-04-02 1987-12-23 Intermediaires pour la preparation de derives de pyrrolidine Expired - Fee Related CA1268472A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000555347A CA1268472A (fr)	1984-04-02	1987-12-23	Intermediaires pour la preparation de derives de pyrrolidine

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
IT20358/84A IT1173768B (it)	1984-04-02	1984-04-02	Procedimento di preparazione di derivati 1-carbamoilmetilici di 4-idrossi-2-osso-pirrolidina nonche' di intermedi per ottenere tali composti
IT20358A/84		1984-04-02
CA000477420A CA1241334A (fr)	1984-04-02	1985-03-25	Procede de production de derives de pyrrolidone
CA000555347A CA1268472A (fr)	1984-04-02	1987-12-23	Intermediaires pour la preparation de derives de pyrrolidine

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000477420A Division CA1241334A (fr)	1984-04-02	1985-03-25	Procede de production de derives de pyrrolidone

Publications (1)

Publication Number	Publication Date
CA1268472A true CA1268472A (fr)	1990-05-01

Family

ID=25670623

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CA000555347A Expired - Fee Related CA1268472A (fr)	1984-04-02	1987-12-23	Intermediaires pour la preparation de derives de pyrrolidine
CA000555348A Expired CA1255326A (fr)	1984-04-02	1987-12-23	Derives d'acide 2-(4-halogeno-3-oxobutanamido) -acetique, produits intermediaires pour la preparation de derives de pyrrolidine

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CA000555348A Expired CA1255326A (fr)	1984-04-02	1987-12-23	Derives d'acide 2-(4-halogeno-3-oxobutanamido) -acetique, produits intermediaires pour la preparation de derives de pyrrolidine

Country Status (1)

Country	Link
CA (2)	CA1268472A (fr)

1987
- 1987-12-23 CA CA000555347A patent/CA1268472A/fr not_active Expired - Fee Related
- 1987-12-23 CA CA000555348A patent/CA1255326A/fr not_active Expired

Also Published As

Publication number	Publication date
CA1255326A (fr)	1989-06-06

Legal Events

Date	Code	Title	Description
1993-11-02	MKLA	Lapsed

Publication	Publication Date	Title
EP1384707B1 (fr)	2005-06-08	4-Nitroxybutylester de naproxene
EP0156655B1 (fr)	1988-11-23	Procédé de préparation de dérivés de pyrrolidone
US5539110A (en)	1996-07-23	Method for the preparation of (-)piperazine benzoxazine derivatives
US5596095A (en)	1997-01-21	Formation and utility of sulfonic acid protecting groups
CA1268472A (fr)	1990-05-01	Intermediaires pour la preparation de derives de pyrrolidine
US5461157A (en)	1995-10-24	Process for preparing pyrrolidinylacetamide derivatives
EP0285270B1 (fr)	1992-06-03	Procédé de préparation de propargyl-1-dioxo-2,4-imidazolidine
EP0839800B1 (fr)	2002-10-23	Procédé de préparation de dérivés d'halogénoacétamide
Dupre et al.	1991	An improved synthesis of ethyl N-(methoxycarbonyl)-2, 5-dihydro-1H-pyrrole-3-carboxylate
US5142091A (en)	1992-08-25	α, β-unsaturated ketones and ketoxime derivatives
US5175313A (en)	1992-12-29	Process for preparing dihydrofuranone derivatives
NO168703B (no)	1991-12-16	Utgangsforbindelse for anvendelse ved fremstilling av pyrrolidinderivater
US5516927A (en)	1996-05-14	2-nitrobenzoyl-3-silyloxyaminoacrylate derivatives and method for the preparation of the same
Panetta et al.	1991	Synthesis of 4-alkyl-2-iodosobenzoic acids: potent catalysts for the hydrolysis of phosphorus esters [Erratum to document cited in CA113 (15): 131664u]
Lehd et al.	1991	Improved radical stabilization energies [Erratum to document cited in CA114 (7): 61271h]
US4716241A (en)	1987-12-29	Cyclopentane derivatives
Lomas et al.	1991	Reactions of thermally generated tert-butyl and di (tert-alkyl) ketyl radicals in toluene: cage effects and hydrogen transfer [Erratum to document cited in CA114 (5): 41737m]
CA1084939A (fr)	1980-09-02	Procede de preparation de nouveaux derives de pyrrolidone
KR100218196B1 (ko)	1999-09-01	2-아미노티아졸 카르복사미드 유도체의 제조방법
JP2001516741A (ja)	2001-10-02	スルホ−ｎ−ヒドロキシスクシンイミドおよびその製造方法
HK1009131B (en)	2003-04-17	Process for preparing halogenoacetamide derivatives
IE45506B1 (en)	1982-09-08	1,5-disubstituted-2-pyrrolidones