IL103414A - Process for the preparation of the lactone of 1r, cis 2, 2-dimethyl-3-formyl-cyclopropane-1-carboxylic acid and internediates therefor - Google Patents

Process for the preparation of the lactone of 1r, cis 2, 2-dimethyl-3-formyl-cyclopropane-1-carboxylic acid and internediates therefor

Info

Publication number: IL103414A
Authority: IL; Israel
Prior art keywords: alkaline; process according; acid; formula; compound
Prior art date: 1991-11-08

Application number

IL10341492A

Other languages

English (en)

Other versions

IL103414A0 (en

Original Assignee

Roussel Uclaf

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.)

1991-11-08

Filing date

1992-10-13

Publication date

1996-08-04

1992-10-13 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1993-03-15 Publication of IL103414A0 publication Critical patent/IL103414A0/xx

1996-08-04 Publication of IL103414A publication Critical patent/IL103414A/en

Links

238000000034 method Methods 0.000 title claims abstract description 22
238000002360 preparation method Methods 0.000 title claims abstract description 7
239000002253 acid Substances 0.000 title claims description 42
150000002596 lactones Chemical class 0.000 title description 21
BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical compound FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 title description 13
150000001875 compounds Chemical class 0.000 claims abstract description 22
239000007800 oxidant agent Substances 0.000 claims abstract description 10
239000000203 mixture Substances 0.000 claims description 28
239000005708 Sodium hypochlorite Substances 0.000 claims description 14
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 14
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 7
239000011777 magnesium Substances 0.000 claims description 7
229910052749 magnesium Inorganic materials 0.000 claims description 7
150000007513 acids Chemical class 0.000 claims description 6
235000011054 acetic acid Nutrition 0.000 claims description 5
238000011065 in-situ storage Methods 0.000 claims description 5
238000002955 isolation Methods 0.000 claims description 5
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 claims description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Chemical compound Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 claims description 4
QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical group ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 4
159000000003 magnesium salts Chemical class 0.000 claims description 4
239000011591 potassium Substances 0.000 claims description 4
229910052700 potassium Inorganic materials 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 3
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 3
239000012286 potassium permanganate Substances 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
229910019142 PO4 Inorganic materials 0.000 claims description 2
150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
239000008346 aqueous phase Substances 0.000 claims description 2
150000001642 boronic acid derivatives Chemical class 0.000 claims description 2
239000011575 calcium Substances 0.000 claims description 2
229910052791 calcium Inorganic materials 0.000 claims description 2
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical class [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
235000011116 calcium hydroxide Nutrition 0.000 claims description 2
150000004679 hydroxides Chemical class 0.000 claims description 2
AAUNBWYUJICUKP-UHFFFAOYSA-N hypoiodite Chemical compound I[O-] AAUNBWYUJICUKP-UHFFFAOYSA-N 0.000 claims description 2
229910052744 lithium Inorganic materials 0.000 claims description 2
YZQBYALVHAANGI-UHFFFAOYSA-N magnesium;dihypochlorite Chemical compound [Mg+2].Cl[O-].Cl[O-] YZQBYALVHAANGI-UHFFFAOYSA-N 0.000 claims description 2
235000021317 phosphate Nutrition 0.000 claims description 2
150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 2
235000011118 potassium hydroxide Nutrition 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
235000011121 sodium hydroxide Nutrition 0.000 claims description 2
150000001243 acetic acids Chemical class 0.000 claims 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 claims 1
150000004672 propanoic acids Chemical class 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
239000000047 product Substances 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
238000013019 agitation Methods 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 13
239000007864 aqueous solution Substances 0.000 description 9
PTQGFDXPHNRDCV-UHFFFAOYSA-N 3-formyl-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C=O)C1C(O)=O PTQGFDXPHNRDCV-UHFFFAOYSA-N 0.000 description 8
238000000605 extraction Methods 0.000 description 8
239000000543 intermediate Substances 0.000 description 8
230000001590 oxidative effect Effects 0.000 description 8
239000004133 Sodium thiosulphate Substances 0.000 description 7
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 7
235000019345 sodium thiosulphate Nutrition 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
230000020477 pH reduction Effects 0.000 description 6
238000001035 drying Methods 0.000 description 5
239000002609 medium Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 4
229910052921 ammonium sulfate Inorganic materials 0.000 description 4
239000001166 ammonium sulphate Substances 0.000 description 4
235000011130 ammonium sulphate Nutrition 0.000 description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
ZKQDCIXGCQPQNV-UHFFFAOYSA-N Calcium hypochlorite Chemical compound [Ca+2].Cl[O-].Cl[O-] ZKQDCIXGCQPQNV-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
JQLDXPJJQAIQCC-UHFFFAOYSA-N 3-[carboxy(hydroxy)methyl]-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C(O)C(O)=O)C1C(O)=O JQLDXPJJQAIQCC-UHFFFAOYSA-N 0.000 description 2
QHAPONCMFJQXEN-UHFFFAOYSA-N 4-hydroxy-6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one Chemical compound O=C1OC(O)C2C1C2(C)C QHAPONCMFJQXEN-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
BFSPAPKTIGPYOV-BQYQJAHWSA-N (e)-1-[4-(4-hydroxyphenyl)piperazin-1-yl]-3-thiophen-2-ylprop-2-en-1-one Chemical compound C1=CC(O)=CC=C1N1CCN(C(=O)\C=C\C=2SC=CC=2)CC1 BFSPAPKTIGPYOV-BQYQJAHWSA-N 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
241000687983 Cerobasis alpha Species 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
230000009102 absorption Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
-1 and preferably Chemical compound 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
LWXVCCOAQYNXNX-UHFFFAOYSA-N lithium hypochlorite Chemical compound [Li+].Cl[O-] LWXVCCOAQYNXNX-UHFFFAOYSA-N 0.000 description 1
229910000403 monosodium phosphate Inorganic materials 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
PNYYBUOBTVHFDN-UHFFFAOYSA-N sodium bismuthate Chemical compound [Na+].[O-][Bi](=O)=O PNYYBUOBTVHFDN-UHFFFAOYSA-N 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
229960001922 sodium perborate Drugs 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Furan Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

IL10341492A 1991-11-08 1992-10-13 Process for the preparation of the lactone of 1r, cis 2, 2-dimethyl-3-formyl-cyclopropane-1-carboxylic acid and internediates therefor IL103414A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR9113775A FR2683525B1 (fr)	1991-11-08	1991-11-08	Nouveau procede de preparation de la lactone de l'acide 1r, cis 2,2-dimethyl 3-formyl cyclopropane-1-carboxylique et intermediaires .

Publications (2)

Publication Number	Publication Date
IL103414A0 IL103414A0 (en)	1993-03-15
IL103414A true IL103414A (en)	1996-08-04

Family

ID=9418740

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10341492A IL103414A (en)	1991-11-08	1992-10-13	Process for the preparation of the lactone of 1r, cis 2, 2-dimethyl-3-formyl-cyclopropane-1-carboxylic acid and internediates therefor

Country Status (27)

Country	Link
US (1)	US5278322A (cs)
EP (1)	EP0541445B1 (cs)
JP (1)	JP3167811B2 (cs)
KR (1)	KR100245059B1 (cs)
CN (1)	CN1035819C (cs)
AR (1)	AR247739A1 (cs)
AT (1)	ATE134372T1 (cs)
AU (1)	AU652329B2 (cs)
BR (1)	BR9204313A (cs)
CA (1)	CA2082286C (cs)
CZ (1)	CZ282006B6 (cs)
DE (1)	DE69208425T2 (cs)
DK (1)	DK0541445T3 (cs)
ES (1)	ES2083713T3 (cs)
FI (1)	FI106125B (cs)
FR (1)	FR2683525B1 (cs)
GR (1)	GR3019109T3 (cs)
HU (1)	HU216976B (cs)
IL (1)	IL103414A (cs)
MX (1)	MX9206355A (cs)
NO (1)	NO301641B1 (cs)
PL (2)	PL171116B1 (cs)
RU (1)	RU2058310C1 (cs)
SK (1)	SK278847B6 (cs)
TR (1)	TR26720A (cs)
UA (1)	UA44884C2 (cs)
ZA (1)	ZA928569B (cs)

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US1379008A (en) *	1919-11-17	1921-05-24	Albert B Frenier	Temperature-producing mechanism and controlling means therefor
US2726250A (en) *	1951-05-15	1955-12-06	Koege Kemisk Vaerk	5-monosubstituted 2-oxo-2, 5-dihydrofurans
US4014918A (en) *	1968-07-12	1977-03-29	Roussel-Uclaf	Process for the preparation of cyclopropane derivatives and compounds produced therein
FR1580474A (cs) *	1968-07-12	1969-09-05
IL32569A (en) *	1968-07-12	1976-06-30	Roussel Uclaf	Process for the preparation of dimethyl cyclopropane carboxylic acid derivatives and some products resulting therefrom
US3694472A (en) *	1970-05-12	1972-09-26	Roussel Uclaf	Synthesis of pyrethric acid
US3965129A (en) *	1973-10-10	1976-06-22	Hoffmann-La Roche Inc.	Optical resolution of organic carboxylic acids
FR2396006A1 (fr) *	1977-06-27	1979-01-26	Roussel Uclaf	Nouveaux composes a noyau cyclopropanique, procede de preparation et application a la preparation de derives cyclopropaniques a chaine dihalovinyliques
US4132717A (en) *	1977-08-09	1979-01-02	Shell Oil Company	Enol lactone intermediate for the preparation of (1R,cis)-caronaldehydic acid
US4518797A (en) *	1978-10-23	1985-05-21	Shell Oil Company	Cyclopropanecarboxylate pesticides and their preparation
FR2479213A1 (fr) *	1980-03-28	1981-10-02	Roussel Uclaf	Procede de preparation d'acide pentenoique possedant une fonction aldehyde
FR2485000A1 (fr) *	1980-06-20	1981-12-24	Roussel Uclaf	4-methyl 3-formyl pentene 1-oates d'alcoyle inferieur, leur procede de preparation et leur application
DE3111849A1 (de) *	1981-03-26	1982-10-14	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von caronaldehydsaeure und deren derivaten

1991
- 1991-11-08 FR FR9113775A patent/FR2683525B1/fr not_active Expired - Lifetime
1992
- 1992-10-06 AR AR92323365A patent/AR247739A1/es active
- 1992-10-08 RU SU925052808A patent/RU2058310C1/ru not_active IP Right Cessation
- 1992-10-13 IL IL10341492A patent/IL103414A/en not_active IP Right Cessation
- 1992-10-29 US US07/968,429 patent/US5278322A/en not_active Expired - Lifetime
- 1992-11-03 TR TR92/1063A patent/TR26720A/xx unknown
- 1992-11-04 SK SK3306-92A patent/SK278847B6/sk unknown
- 1992-11-04 CZ CS923306A patent/CZ282006B6/cs not_active IP Right Cessation
- 1992-11-05 DK DK92402994.5T patent/DK0541445T3/da active
- 1992-11-05 DE DE69208425T patent/DE69208425T2/de not_active Expired - Lifetime
- 1992-11-05 AT AT92402994T patent/ATE134372T1/de not_active IP Right Cessation
- 1992-11-05 ES ES92402994T patent/ES2083713T3/es not_active Expired - Lifetime
- 1992-11-05 MX MX9206355A patent/MX9206355A/es unknown
- 1992-11-05 EP EP92402994A patent/EP0541445B1/fr not_active Expired - Lifetime
- 1992-11-06 FI FI925050A patent/FI106125B/fi not_active IP Right Cessation
- 1992-11-06 PL PL92312901A patent/PL171116B1/pl not_active IP Right Cessation
- 1992-11-06 HU HU9203489A patent/HU216976B/hu unknown
- 1992-11-06 CA CA002082286A patent/CA2082286C/fr not_active Expired - Lifetime
- 1992-11-06 ZA ZA928569A patent/ZA928569B/xx unknown
- 1992-11-06 AU AU28186/92A patent/AU652329B2/en not_active Ceased
- 1992-11-06 NO NO924276A patent/NO301641B1/no not_active IP Right Cessation
- 1992-11-06 JP JP32137192A patent/JP3167811B2/ja not_active Expired - Lifetime
- 1992-11-06 PL PL92296514A patent/PL171284B1/pl not_active IP Right Cessation
- 1992-11-06 BR BR929204313A patent/BR9204313A/pt not_active IP Right Cessation
- 1992-11-07 CN CN92112856A patent/CN1035819C/zh not_active Expired - Lifetime
- 1992-11-07 KR KR1019920020869A patent/KR100245059B1/ko not_active Expired - Lifetime
1993
- 1993-11-08 UA UA93003082A patent/UA44884C2/uk unknown
1996
- 1996-02-27 GR GR950401766T patent/GR3019109T3/el unknown

Also Published As

Publication number	Publication date
PL296514A1 (en)	1993-07-12
HU216976B (hu)	1999-10-28
ZA928569B (en)	1993-11-08
EP0541445A1 (fr)	1993-05-12
FI925050L (fi)	1993-05-09
CZ330692A3 (en)	1993-08-11
FR2683525A1 (fr)	1993-05-14
PL171284B1 (en)	1997-03-28
FR2683525B1 (fr)	1994-01-21
IL103414A0 (en)	1993-03-15
DK0541445T3 (da)	1996-04-09
SK330692A3 (en)	1998-03-04
DE69208425D1 (de)	1996-03-28
BR9204313A (pt)	1993-05-18
FI925050A0 (fi)	1992-11-06
DE69208425T2 (de)	1996-09-05
UA44884C2 (uk)	2002-03-15
JPH05222025A (ja)	1993-08-31
ATE134372T1 (de)	1996-03-15
AU2818692A (en)	1993-05-13
CA2082286A1 (fr)	1993-05-09
RU2058310C1 (ru)	1996-04-20
NO301641B1 (no)	1997-11-24
CN1035819C (zh)	1997-09-10
AR247739A1 (es)	1995-03-31
KR100245059B1 (ko)	2000-03-02
EP0541445B1 (fr)	1996-02-21
ES2083713T3 (es)	1996-04-16
KR930010018A (ko)	1993-06-21
NO924276D0 (no)	1992-11-06
FI106125B (fi)	2000-11-30
NO924276L (no)	1993-05-10
US5278322A (en)	1994-01-11
SK278847B6 (sk)	1998-03-04
HU9203489D0 (en)	1993-03-01
MX9206355A (es)	1994-03-31
HUT63156A (en)	1993-07-28
CZ282006B6 (cs)	1997-04-16
AU652329B2 (en)	1994-08-18
CN1072930A (zh)	1993-06-09
PL171116B1 (pl)	1997-03-28
TR26720A (tr)	1995-05-15
CA2082286C (fr)	2001-02-27
GR3019109T3 (en)	1996-05-31
JP3167811B2 (ja)	2001-05-21

Legal Events

Date	Code	Title
1997-01-10	FF	Patent granted
1997-06-10	KB	Patent renewed
1999-04-11	KB	Patent renewed
2003-01-12	KB	Patent renewed
2003-02-12	HCA	Change of name of proprietor(s) after amalgamation
2007-02-12	KB	Patent renewed
2010-12-30	KB	Patent renewed
2013-05-30	EXP	Patent expired

Publication	Publication Date	Title
SU1075970A3 (ru)	1984-02-23	Способ получени цис-производных дигалоидвинилциклопропана
US4156692A (en)	1979-05-29	Mixed anhydride of acetic acid and (1R,cis)-caronaldehydic acids
IL30735A (en)	1970-12-24	Process for preparing tetra and hexa hydroindane derivatives
DE1593720A1 (de)	1970-12-03	Ester der von Diformylmethylenmethancarbonsaeure
US5278322A (en)	1994-01-11	Process
SU1731042A3 (ru)	1992-04-30	Способ получени производных бензола
EP0541446B1 (fr)	1996-02-28	Nouveau procédé de préparation de la lactone de l'acide 1R,cis 2,2-diméthyl 3-formyl cyclopropane-1-carboxylique et intermédiaires halogénés
HU208125B (en)	1993-08-30	Process for producing 2,3-dihydro-4,6,7-trimethyl-2-(rs)-benzofuranacetic acid derivatives
JPH0437830B2 (cs)	1992-06-22
HU191592B (en)	1987-03-30	Process for preparing isoxazole-derivatives
JPH0242826B2 (cs)	1990-09-26
HU177583B (en)	1981-11-28	Process for resolving alkali salts and lactone of raceme cys-2-hydroxy-cyclopent-4-ene-1-yl-acetic acid with optically active alpha-phenyl-ethylamine
CH370792A (fr)	1963-07-31	Procédé de synthèse d'alcaloïdes de la série de la réserpine
CH296181A (fr)	1954-01-31	Procédé de préparation du thréo-1-p-nitrophényl-2-dichloracétamido-propanediol-1,3.
HU180688B (hu)	1983-04-29	Módosított eljárás 6-fenil-acetamido-2,2-dimetil- -penam - 3-karbonsav-2- (dimetil- amino) - etil - észter- - hidrojodid előállítására
JPH0435463B2 (cs)	1992-06-11
JPH11147869A (ja)	1999-06-02	３−カルボキシ−１−フェニル−２−ピロリジノン誘導体および製造法