DD264695A1 - Verfahren zur herstellung von hochreinen cyclischen estern - Google Patents

Verfahren zur herstellung von hochreinen cyclischen estern Download PDF

Info

Publication number: DD264695A1
Authority: DD; German Democratic Republic
Prior art keywords: process according; polyether; thermally stable; ester; core
Prior art date: 1985-07-11

Application number

DD87308357A

Other languages

German (de)

English (en)

Inventor

Harold E Bellis

Original Assignee

Du Pont

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.)

1985-07-11

Filing date

1987-10-28

Publication date

1989-02-08

1987-10-28 Application filed by Du Pont filed Critical Du Pont

1989-02-08 Publication of DD264695A1 publication Critical patent/DD264695A1/de

Links

238000000034 method Methods 0.000 title claims abstract description 34
150000002148 esters Chemical class 0.000 title claims abstract description 14
238000004519 manufacturing process Methods 0.000 title description 6
239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 29
229920000570 polyether Polymers 0.000 claims abstract description 29
229940061720 alpha hydroxy acid Drugs 0.000 claims abstract description 8
150000001280 alpha hydroxy acids Chemical class 0.000 claims abstract description 8
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
-1 cyclic ester Chemical class 0.000 claims description 12
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 10
230000015572 biosynthetic process Effects 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 7
125000001931 aliphatic group Chemical group 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 4
229910052753 mercury Inorganic materials 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
229920001400 block copolymer Polymers 0.000 claims description 3
LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 claims description 2
229940116333 ethyl lactate Drugs 0.000 claims description 2
235000014655 lactic acid Nutrition 0.000 claims description 2
239000004310 lactic acid Substances 0.000 claims description 2
229940057867 methyl lactate Drugs 0.000 claims description 2
238000001953 recrystallisation Methods 0.000 claims description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims 1
230000015556 catabolic process Effects 0.000 claims 1
238000006731 degradation reaction Methods 0.000 claims 1
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 1
238000004090 dissolution Methods 0.000 claims 1
238000004064 recycling Methods 0.000 claims 1
229920001577 copolymer Polymers 0.000 abstract description 5
125000004122 cyclic group Chemical group 0.000 abstract description 5
238000010438 heat treatment Methods 0.000 abstract description 4
RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 description 14
229960004275 glycolic acid Drugs 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000000843 powder Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000002253 acid Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
238000004227 thermal cracking Methods 0.000 description 2
OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical group C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
238000013494 PH determination Methods 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
229920000954 Polyglycolide Polymers 0.000 description 1
229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
238000005336 cracking Methods 0.000 description 1
ZANNOFHADGWOLI-UHFFFAOYSA-N ethyl 2-hydroxyacetate Chemical compound CCOC(=O)CO ZANNOFHADGWOLI-UHFFFAOYSA-N 0.000 description 1
239000012530 fluid Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
150000001261 hydroxy acids Chemical class 0.000 description 1
239000007943 implant Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000011707 mineral Substances 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000000399 orthopedic effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004633 polyglycolic acid Substances 0.000 description 1
239000002685 polymerization catalyst Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
238000002411 thermogravimetry Methods 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/12—1,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Polyesters Or Polycarbonates (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Polyethers (AREA)
Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
Medicinal Preparation (AREA)
Materials For Medical Uses (AREA)

DD87308357A 1985-07-11 1987-10-28 Verfahren zur herstellung von hochreinen cyclischen estern DD264695A1 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US75390785A	1985-07-11	1985-07-11
US06/925,484 US4727163A (en)	1985-07-11	1986-10-29	Process for preparing highly pure cyclic esters

Publications (1)

Publication Number	Publication Date
DD264695A1 true DD264695A1 (de)	1989-02-08

Family

ID=25451798

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87308357A DD264695A1 (de)	1985-07-11	1987-10-28	Verfahren zur herstellung von hochreinen cyclischen estern

Country Status (17)

Country	Link
US (1)	US4727163A (fr)
EP (1)	EP0266143B1 (fr)
JP (1)	JPS63152375A (fr)
KR (1)	KR880005116A (fr)
CN (1)	CN1015986B (fr)
AR (1)	AR243879A1 (fr)
AT (1)	ATE102617T1 (fr)
AU (1)	AU591432B2 (fr)
BR (1)	BR8705758A (fr)
CA (1)	CA1277672C (fr)
DD (1)	DD264695A1 (fr)
DE (1)	DE3789274D1 (fr)
IE (1)	IE872885L (fr)
IL (1)	IL84303A (fr)
MX (1)	MX165197B (fr)
PT (1)	PT86017B (fr)
ZA (1)	ZA878121B (fr)

Families Citing this family (54)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0264926B1 (fr) *	1986-10-24	1992-04-08	Boehringer Ingelheim Kg	Procédé de préparation et de purification de composés thermolabiles
DE3781133T2 (de) *	1986-12-19	1993-06-24	Akzo Nv	Herstellung von polymilchsaeure und copolymeren daraus.
US4835293A (en) *	1987-02-24	1989-05-30	E. I. Du Pont De Nemours And Company	Atmospheric pressure process for preparing pure cyclic esters
US5214159A (en) *	1987-06-16	1993-05-25	Boehringer Ingelheim Gmbh	Meso-lactide
US5023349A (en) *	1990-05-08	1991-06-11	E. I. Du Pont De Nemours And Company	Continuous process for rapid conversion of oligomers to cyclic esters
US5091544A (en) *	1990-05-08	1992-02-25	E. I. Du Pont De Nemours And Company	Process for rapid conversion of oligomers to cyclic esters
AU7762291A (en) *	1990-05-03	1991-11-27	E.I. Du Pont De Nemours And Company	Improved process for the rapid production of cyclic esters
US5138074A (en) *	1990-06-28	1992-08-11	E. I. Du Pont De Nemours And Company	Continuous catalyzed vapor phase dimeric cyclic ester process
AU8283391A (en) *	1990-07-13	1992-02-04	E.I. Du Pont De Nemours And Company	High yield recycle process for lactide
US5076983A (en) *	1990-07-16	1991-12-31	E. I. Du Pont De Nemours And Company	Polyhydroxy acid films
US5332839A (en) *	1990-09-18	1994-07-26	Biopak Technology, Ltd.	Catalytic production of lactide directly from lactic acid
US5266706A (en) *	1990-10-23	1993-11-30	E. I. Du Pont De Nemours & Company	Solvent scrubbing recovery of lactide and other dimeric cyclic esters
US5117008A (en) *	1990-10-23	1992-05-26	E. I. Du Pont De Nemours And Company	Solvent scrubbing recovery of lactide and other dimeric cyclic esters
US5089632A (en) *	1991-01-30	1992-02-18	E. I. Du Pont De Nemours And Company	Process for preparing cyclic esters using a fluorocarbon
US5326887A (en) *	1991-02-27	1994-07-05	E. I. Du Pont De Nemours And Company	Process for the preparation of 1,4-dioxane-2,5-diones
US5196551A (en) *	1991-06-24	1993-03-23	E. I. Du Pont De Nemours And Company	Co-vaporization process for preparing lactide
US5264617A (en) *	1991-11-22	1993-11-23	E. I. Du Pont De Nemours And Company	Preparation of alkyl esters by depolymerization
US5264626A (en) *	1991-11-22	1993-11-23	E. I. Du Pont De Nemours And Company	Rapid depolymerization of polyhydroxy acids
US5229528A (en) *	1991-11-22	1993-07-20	E. I. Du Pont De Nemours And Company	Rapid depolymerization of polyhydroxy acids
US5268507A (en) *	1991-11-22	1993-12-07	E. I. Du Pont De Nemours And Company	Preparation of amide derivatives of hydroxy acids
US5264614A (en) *	1991-11-22	1993-11-23	E. I. Du Pont De Nemours And Company	Recovery of polyhydroxy acids
US5142023A (en) *	1992-01-24	1992-08-25	Cargill, Incorporated	Continuous process for manufacture of lactide polymers with controlled optical purity
US5247059A (en) *	1992-01-24	1993-09-21	Cargill, Incorporated	Continuous process for the manufacture of a purified lactide from esters of lactic acid
US6005067A (en) *	1992-01-24	1999-12-21	Cargill Incorporated	Continuous process for manufacture of lactide polymers with controlled optical purity
US6326458B1 (en)	1992-01-24	2001-12-04	Cargill, Inc.	Continuous process for the manufacture of lactide and lactide polymers
US5247058A (en) *	1992-01-24	1993-09-21	Cargill, Incorporated	Continuous process for manufacture of lactide polymers with controlled optical purity
US5258488A (en) *	1992-01-24	1993-11-02	Cargill, Incorporated	Continuous process for manufacture of lactide polymers with controlled optical purity
US5420304A (en) *	1992-03-19	1995-05-30	Biopak Technology, Ltd.	Method to produce cyclic esters
US5686630A (en) *	1993-09-29	1997-11-11	Chronopol, Inc.	Purifying cyclic esters by aqueous solvent extraction
US5675021A (en) *	1992-03-19	1997-10-07	Chronopol, Inc.	Method to produce and purify cyclic esters
US5278256A (en) *	1992-09-16	1994-01-11	E. I. Du Pont De Nemours And Company	Rapidly degradable poly (hydroxyacid) compositions
US6005068A (en)	1992-10-02	1999-12-21	Cargill Incorporated	Melt-stable amorphous lactide polymer film and process for manufacture thereof
NZ256978A (en) *	1992-10-02	1996-05-28	Cargill Inc	Paper product coated with a poly(lactide) composition comprising no more than 5 wt % lactide monomer, the poly(lactide) having a number average mw of 10,000 to 200,000
DE69330046T2 (de) *	1992-10-02	2001-11-15	Cargill, Inc.	Schmelzstabiles lactidpolymergewebe und verfahren zu seiner herstellung
US5338822A (en) *	1992-10-02	1994-08-16	Cargill, Incorporated	Melt-stable lactide polymer composition and process for manufacture thereof
US5342969A (en) *	1993-03-03	1994-08-30	E. I. Du Pont De Nemours And Company	Recovery of hydroxycarboxylic acid values from poly(hydroxycarboxylic acids)
EP0789080B1 (fr)	1996-02-08	2002-01-16	Gesellschaft für ökologische Technologie und Systemanalyse e.V.	Procédé de préparation de lactates d'aminium organiques et leur utilisation pour le préparation de dilactide
US5830991A (en) *	1996-02-09	1998-11-03	Kureha Kagaku Kagyo Kk	Preparation process and purification process of dimeric cyclic ester of hydroxycarboxylic acid
JP4565208B2 (ja)	2000-03-31	2010-10-20	株式会社クレハ	グリコリドの精製方法
WO2002014303A1 (fr) *	2000-08-11	2002-02-21	Kureha Kagaku Kogyo K.K.	Procede de preparation d'esters cycliques et procede de purification desdits esters
EP1366037B1 (fr) *	2001-03-06	2005-08-24	Kureha Kagaku Kogyo Kabushiki Kaisha	Procede de fabrication de glycolides et composition d'acide glycolique
CA2440379C (fr) *	2001-04-12	2011-01-04	Kureha Chemical Industry Company, Limited	Procede de production de glycolide et oligomere d'acide glycolique pour la production de glycolide
WO2006129736A1 (fr) *	2005-06-01	2006-12-07	Mitsui Chemicals, Inc.	Procédé pour produire un ester cyclique
EP2516413B1 (fr) *	2009-12-21	2016-04-13	Evonik Corporation	Procédé de préparation d'esters cycliques comprenant des groupes fonctionnels insaturés et polyesters préparés à partir de ceux-ci
US20120245322A1 (en)	2011-03-25	2012-09-27	Hyundai Motor Company	Manufacturing lactide from lactic acid
US20120245321A1 (en)	2011-03-25	2012-09-27	Hyundai Motor Company	Manufacturing lactide from lactic acid
KR101326521B1 (ko)	2011-05-26	2013-11-07	현대자동차주식회사	유산으로부터 락타이드의 제조 방법
US9284294B2 (en)	2012-02-09	2016-03-15	Novus International, Inc.	Functionalized polymer compositions
PL2871973T3 (pl)	2012-07-12	2019-02-28	Novus International Inc.	Kompozycje matrycy i warstwy do ochrony środków bioaktywnych
JP6326373B2 (ja)	2012-11-22	2018-05-16	株式会社クレハ	気液の向流接触による精留工程を備えるグリコリドの製造方法、及び、粗グリコリドの精製方法
US10584306B2 (en)	2017-08-11	2020-03-10	Board Of Regents Of The University Of Oklahoma	Surfactant microemulsions
RU2660652C1 (ru) *	2017-12-29	2018-07-09	Федеральное государственное автономное образовательное учреждение высшего образования "Национальный исследовательский Томский государственный университет" (ТГУ, НИ ТГУ)	Способ получения гликолида из модифицированных олигомеров гликолевой кислоты
CN109970702B (zh) *	2019-03-28	2020-06-26	杭州华惟生物医药有限公司	一种高纯度医用乙交酯的工业化生产方法
CN117903105A (zh)	2022-10-12	2024-04-19	中国石油化工股份有限公司	一种乙交酯的提纯方法、乙交酯及应用

Family Cites Families (10)

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Publication number	Priority date	Publication date	Assignee	Title
US2163268A (en) *	1933-12-12	1939-06-20	Du Pont	Method for making cyclic esters
US2163109A (en) *	1936-04-03	1939-06-20	Du Pont	Chemical process and products therefrom
US2668162A (en) *	1952-03-20	1954-02-02	Du Pont	Preparation of high molecular weight polyhydroxyacetic ester
FR1485302A (fr) *	1966-07-01	1967-06-16	Wolfen Filmfab Veb	Procédé pour l'obtention d'esters-anhydrides cycliques d'acides alpha-hydroxy-carboxyliques
US3442871A (en) *	1966-05-04	1969-05-06	American Cyanamid Co	Process for polymerizing a glycolide
GB1108720A (en) *	1966-10-10	1968-04-03	Wolfen Filmfab Veb	Process for the manufacture of cyclic ester anhydrides of ª-hydroxy-carboxylic acids
US3457280A (en) *	1967-06-12	1969-07-22	American Cyanamid Co	Alpha-glycolide and methods for the isolation thereof
US3435008A (en) *	1967-08-22	1969-03-25	American Cyanamid Co	Method for preparation of isomerically pure beta-glycolide and polymerization method for glycolide compositions employing partial hydrolyzate of said beta-glycolide
US3597350A (en) *	1968-11-12	1971-08-03	Pharmacia Fine Chemicals Ab	Gel filtration process
US3763190A (en) *	1972-04-19	1973-10-02	Stanford Research Inst	Preparation of pure glycolide

1986
- 1986-10-29 US US06/925,484 patent/US4727163A/en not_active Expired - Fee Related
1987
- 1987-10-22 CA CA000549976A patent/CA1277672C/fr not_active Expired - Lifetime
- 1987-10-26 AT AT87309416T patent/ATE102617T1/de not_active IP Right Cessation
- 1987-10-26 DE DE87309416T patent/DE3789274D1/de not_active Expired - Lifetime
- 1987-10-26 EP EP87309416A patent/EP0266143B1/fr not_active Expired - Lifetime
- 1987-10-28 AR AR87309150A patent/AR243879A1/es active
- 1987-10-28 MX MX9002A patent/MX165197B/es unknown
- 1987-10-28 DD DD87308357A patent/DD264695A1/de not_active IP Right Cessation
- 1987-10-28 JP JP62272900A patent/JPS63152375A/ja active Pending
- 1987-10-28 IE IE872885A patent/IE872885L/xx unknown
- 1987-10-28 BR BR8705758A patent/BR8705758A/pt unknown
- 1987-10-28 IL IL84303A patent/IL84303A/xx not_active IP Right Cessation
- 1987-10-28 AU AU80417/87A patent/AU591432B2/en not_active Ceased
- 1987-10-28 KR KR870011957A patent/KR880005116A/ko not_active Ceased
- 1987-10-28 PT PT86017A patent/PT86017B/pt not_active IP Right Cessation
- 1987-10-28 CN CN87107549A patent/CN1015986B/zh not_active Expired
- 1987-10-29 ZA ZA878121A patent/ZA878121B/xx unknown

Also Published As

Publication number	Publication date
BR8705758A (pt)	1988-05-31
KR880005116A (ko)	1988-06-28
AR243879A1 (es)	1993-09-30
PT86017B (pt)	1990-07-31
CN1015986B (zh)	1992-03-25
EP0266143A3 (en)	1990-03-07
PT86017A (en)	1987-11-01
AU591432B2 (en)	1989-11-30
MX165197B (es)	1992-10-30
EP0266143B1 (fr)	1994-03-09
DE3789274D1 (de)	1994-04-14
AU8041787A (en)	1988-05-05
JPS63152375A (ja)	1988-06-24
IL84303A (en)	1993-01-14
ATE102617T1 (de)	1994-03-15
IL84303A0 (en)	1988-03-31
CA1277672C (fr)	1990-12-11
EP0266143A2 (fr)	1988-05-04
ZA878121B (en)	1989-07-26
US4727163A (en)	1988-02-23
CN87107549A (zh)	1988-05-11
IE872885L (en)	1988-04-29

Legal Events

Date	Code	Title	Description
1997-08-14	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD264695A1 (de)	1989-02-08	Verfahren zur herstellung von hochreinen cyclischen estern
DE2721264C2 (de)	1984-07-19	Verfahren zur Herstellung von Di-n-propylessigsäure und deren nichttoxischen Alkali- und Erdalkalimetallsalzen
DE2710242A1 (de)	1977-09-22	5-eckige klammer auf 1,1-diphenyl- 3-(5- oder 6-hydroxy-2-azabicyclo eckige klammer auf 2,2,2 eckige klammer zu oct-2-yl)propyl eckige klammer zu -2- alkyl-1,3,4-oxadiazole und verwandte verbindungen
DE10337773A1 (de)	2005-03-24	Kristallisation von festen Formen von Clopidogrel-Additionssalzen
EP0745593B1 (fr)	2001-01-17	Procédé pour la préparation de 4,6-dichlorompyrimidine pure
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