DD300104A5 - Substituierte isoxazolidine und isoxazoline - Google Patents

Substituierte isoxazolidine und isoxazoline Download PDF

Info

Publication number: DD300104A5
Authority: DD; German Democratic Republic
Prior art keywords: propylpentyl; compounds; mixture; compound; added
Prior art date: 1989-05-24

Application number

DD340953A

Other languages

German (de)

English (en)

Original Assignee

Pharmacia Ab

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.)

1989-05-24

Filing date

1990-05-23

Publication date

1992-05-21

1989-05-24 Priority claimed from SE8901838A external-priority patent/SE8901838D0/xx

1989-05-24 Priority claimed from SE8901837A external-priority patent/SE8901837D0/xx

1990-05-23 Application filed by Pharmacia Ab filed Critical Pharmacia Ab

1992-05-21 Publication of DD300104A5 publication Critical patent/DD300104A5/de

Links

150000002546 isoxazolidines Chemical class 0.000 title abstract description 8
WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical class C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 title 1
238000002360 preparation method Methods 0.000 claims abstract description 18
238000000034 method Methods 0.000 claims abstract description 17
QSFOWAYMMZCQNF-UHFFFAOYSA-N delmopinol Chemical compound CCCC(CCC)CCCC1COCCN1CCO QSFOWAYMMZCQNF-UHFFFAOYSA-N 0.000 claims abstract description 15
229960003854 delmopinol Drugs 0.000 claims abstract description 12
150000001875 compounds Chemical class 0.000 claims description 36
-1 4-propylheptyl compound Chemical class 0.000 claims description 22
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 10
230000002829 reductive effect Effects 0.000 claims description 4
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000001309 chloro group Chemical class Cl* 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 3
MXRGQXCJGSNKHN-UHFFFAOYSA-N 2-[3-(4-methylheptyl)morpholin-4-yl]ethanol Chemical compound CCCC(C)CCCC1COCCN1CCO MXRGQXCJGSNKHN-UHFFFAOYSA-N 0.000 claims description 2
230000029936 alkylation Effects 0.000 claims description 2
238000005804 alkylation reaction Methods 0.000 claims description 2
239000000543 intermediate Substances 0.000 abstract description 6
150000002547 isoxazolines Chemical class 0.000 abstract description 4
238000004519 manufacturing process Methods 0.000 abstract description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
239000000203 mixture Substances 0.000 description 31
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000001704 evaporation Methods 0.000 description 10
230000008020 evaporation Effects 0.000 description 10
238000010992 reflux Methods 0.000 description 10
238000001035 drying Methods 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000011734 sodium Substances 0.000 description 9
239000012074 organic phase Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
239000012267 brine Substances 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 5
239000012071 phase Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
238000009835 boiling Methods 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
MCFJLLFFCSTWHV-UHFFFAOYSA-N 2-propylpentyl 4-methylbenzenesulfonate Chemical compound CCCC(CCC)COS(=O)(=O)C1=CC=C(C)C=C1 MCFJLLFFCSTWHV-UHFFFAOYSA-N 0.000 description 2
HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
RLUDGGHEFUDPLJ-UHFFFAOYSA-N 4-propylhept-1-en-4-ol Chemical compound CCCC(O)(CCC)CC=C RLUDGGHEFUDPLJ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
229910004803 Na2 WO4.2H2 O Inorganic materials 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
150000001336 alkenes Chemical group 0.000 description 2
244000309464 bull Species 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
150000002917 oxazolidines Chemical class 0.000 description 2
239000000047 product Substances 0.000 description 2
238000007142 ring opening reaction Methods 0.000 description 2
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
KKFDCBRMNNSAAW-UHFFFAOYSA-N 2-(morpholin-4-yl)ethanol Chemical compound OCCN1CCOCC1 KKFDCBRMNNSAAW-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
LASHFHLFDRTERB-UHFFFAOYSA-N 2-propylpentan-1-ol Chemical compound CCCC(CO)CCC LASHFHLFDRTERB-UHFFFAOYSA-N 0.000 description 1
QXDOFVVNXBGLKK-UHFFFAOYSA-N 3-Isoxazolidinone Chemical class OC1=NOCC1 QXDOFVVNXBGLKK-UHFFFAOYSA-N 0.000 description 1
OURXRFYZEOUCRM-UHFFFAOYSA-N 4-hydroxymorpholine Chemical compound ON1CCOCC1 OURXRFYZEOUCRM-UHFFFAOYSA-N 0.000 description 1
FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
QDLRPSGGHGMWBC-UHFFFAOYSA-N ON=CN1CCOCC1 Chemical compound ON=CN1CCOCC1 QDLRPSGGHGMWBC-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001345 alkine derivatives Chemical group 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
238000006298 dechlorination reaction Methods 0.000 description 1
150000002011 dioses Chemical class 0.000 description 1
238000006056 electrooxidation reaction Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000001030 gas--liquid chromatography Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
WMWSRIHFAVOHSW-UHFFFAOYSA-N lithium;ethane-1,2-diamine;ethyne Chemical compound [Li+].[C-]#C.NCCN WMWSRIHFAVOHSW-UHFFFAOYSA-N 0.000 description 1
DQEUYIQDSMINEY-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C=C DQEUYIQDSMINEY-UHFFFAOYSA-M 0.000 description 1
229910000474 mercury oxide Inorganic materials 0.000 description 1
UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 1
150000002780 morpholines Chemical class 0.000 description 1
239000002324 mouth wash Substances 0.000 description 1
229940051866 mouthwash Drugs 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
229920001223 polyethylene glycol 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
239000002243 precursor Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000606 toothpaste Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Saccharide Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Photoreceptors In Electrophotography (AREA)
Luminescent Compositions (AREA)
Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Peptides Or Proteins (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

DD340953A 1989-05-24 1990-05-23 Substituierte isoxazolidine und isoxazoline DD300104A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE8901838A SE8901838D0 (sv)	1989-05-24	1989-05-24	New process and intermediates
SE8901837A SE8901837D0 (sv)	1989-05-24	1989-05-24	Substituted isoxazolidines and isoxazolines

Publications (1)

Publication Number	Publication Date
DD300104A5 true DD300104A5 (de)	1992-05-21

Family

ID=26660511

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD340953A DD300104A5 (de)	1989-05-24	1990-05-23	Substituierte isoxazolidine und isoxazoline

Country Status (26)

Country	Link
US (1)	US5155220A (da)
EP (1)	EP0426826B1 (da)
JP (1)	JP3042876B2 (da)
KR (1)	KR0176248B1 (da)
CN (1)	CN1039325C (da)
AT (1)	ATE104968T1 (da)
AU (1)	AU631648B2 (da)
CA (2)	CA2032513C (da)
DD (1)	DD300104A5 (da)
DE (1)	DE69008486T2 (da)
DK (1)	DK0426826T3 (da)
ES (1)	ES2053195T3 (da)
FI (1)	FI97057C (da)
GE (1)	GEP19971047B (da)
GR (1)	GR1001407B (da)
HU (1)	HU205118B (da)
IE (1)	IE65640B1 (da)
IL (1)	IL94427A (da)
LV (1)	LV10276B (da)
MD (1)	MD423C2 (da)
NO (2)	NO179870C (da)
NZ (1)	NZ233730A (da)
PH (1)	PH31619A (da)
PT (1)	PT94131B (da)
RU (1)	RU2042670C1 (da)
WO (1)	WO1990014342A1 (da)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5147632A (en) *	1990-10-31	1992-09-15	Warner-Lambert Company	Anti-plaque compositions comprising a combination of morpholinoamino alcohol and chelating agent
GB9226857D0 (en) *	1992-12-23	1993-02-17	Boyd Edward A	Pharmaceutical compositions
US5552757A (en) *	1994-05-27	1996-09-03	Littelfuse, Inc.	Surface-mounted fuse device
US6878004B2 (en) *	2002-03-04	2005-04-12	Littelfuse, Inc.	Multi-element fuse array
ATE348818T1 (de)	2003-06-12	2007-01-15	Btg Int Ltd	Cyclische hydroxylamine als psychoactive verbindugen
DE112004002301T5 (de) *	2003-11-26	2006-09-28	Littelfuse, Inc., Des Plaines	Elektrische Schutzeinrichtung für ein Fahrzeug und System, das diese einsetzt
GB0523435D0 (en) *	2005-11-17	2005-12-28	Sinclair Pharmaceuticals Ltd	Process
EP3184150B1 (en)	2005-11-22	2019-06-19	Maelor Laboratories Limited	Treatment of sub-gingival pocket infections
GB0602424D0 (en)	2006-02-07	2006-03-22	Sinclair Pharmaceuticals Ltd	Compounds
GB0604018D0 (en) *	2006-02-28	2006-04-05	Sinclair Pharmaceuticals Ltd	Method
GB0615814D0 (en)	2006-08-09	2006-09-20	Sinclair Pharmaceuticals Ltd	Medicament
GB201105162D0 (en)	2011-03-28	2011-05-11	Lane Jonathan	Improved deodorant formulations
IT201600130729A1 (it)	2016-12-23	2018-06-23	Lundbeck Pharmaceuticals Italy S P A	Processo per la produzione degli intermedi del delmopinolo
IT201600130538A1 (it)	2016-12-23	2018-06-23	Lundbeck Pharmaceuticals Italy S P A	Processo per la produzione del delmopinolo
IT201600130642A1 (it)	2016-12-23	2018-06-23	Lundbeck Pharmaceuticals Italy S P A	Processo per la produzione di 2(3 alchilmorfolino)-etan-1-olo
IT201700076821A1 (it)	2017-08-24	2019-02-24	Lundbeck Pharmaceuticals Italy S P A	Nuovo sale del delmopinolo
WO2021155350A1 (en) *	2020-01-31	2021-08-05	You First Services, Inc.	Methods of making delmopinol and salts thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE439011B (sv) *	1980-03-21	1985-05-28	Ferrosan Ab	Morfolinoforeningar, kompositioner innehallande dessa och anvendning derav
JPS59164762A (ja) *	1983-03-09	1984-09-17	Univ Osaka	第２アミンからニトロンを合成する方法

1990
- 1990-05-14 DE DE69008486T patent/DE69008486T2/de not_active Expired - Lifetime
- 1990-05-14 CA CA002032513A patent/CA2032513C/en not_active Expired - Lifetime
- 1990-05-14 AU AU56758/90A patent/AU631648B2/en not_active Expired
- 1990-05-14 US US07/634,186 patent/US5155220A/en not_active Expired - Lifetime
- 1990-05-14 AT AT9090908724T patent/ATE104968T1/de not_active IP Right Cessation
- 1990-05-14 WO PCT/SE1990/000323 patent/WO1990014342A1/en not_active Ceased
- 1990-05-14 EP EP90908724A patent/EP0426826B1/en not_active Expired - Lifetime
- 1990-05-14 JP JP2508104A patent/JP3042876B2/ja not_active Expired - Lifetime
- 1990-05-14 CA CA002187114A patent/CA2187114C/en not_active Expired - Lifetime
- 1990-05-14 ES ES90908724T patent/ES2053195T3/es not_active Expired - Lifetime
- 1990-05-14 DK DK90908724.9T patent/DK0426826T3/da active
- 1990-05-14 HU HU905108A patent/HU205118B/hu unknown
- 1990-05-15 IE IE174890A patent/IE65640B1/en not_active IP Right Cessation
- 1990-05-17 IL IL9442790A patent/IL94427A/en not_active IP Right Cessation
- 1990-05-18 NZ NZ233730A patent/NZ233730A/xx unknown
- 1990-05-23 DD DD340953A patent/DD300104A5/de unknown
- 1990-05-23 GR GR900100397A patent/GR1001407B/el not_active IP Right Cessation
- 1990-05-23 PT PT94131A patent/PT94131B/pt not_active IP Right Cessation
- 1990-05-23 CN CN90103088A patent/CN1039325C/zh not_active Expired - Lifetime
1991
- 1991-01-11 NO NO910131A patent/NO179870C/no not_active IP Right Cessation
- 1991-01-11 FI FI910148A patent/FI97057C/fi active
- 1991-01-23 RU SU914894641A patent/RU2042670C1/ru active
- 1991-01-24 KR KR1019910700084A patent/KR0176248B1/ko not_active Expired - Fee Related
- 1991-05-14 NO NO911873A patent/NO180120C/no not_active IP Right Cessation
1993
- 1993-06-15 LV LVP-93-582A patent/LV10276B/en unknown
- 1993-07-27 GE GEAP19931228A patent/GEP19971047B/en unknown
- 1993-09-07 PH PH46833A patent/PH31619A/en unknown
1994
- 1994-07-14 MD MD95-0039A patent/MD423C2/ro unknown

Also Published As

Publication number	Publication date
CN1048218A (zh)	1991-01-02
US5155220A (en)	1992-10-13
FI910148A0 (fi)	1991-01-11
KR0176248B1 (en)	1999-03-20
DE69008486D1 (de)	1994-06-01
KR920701181A (ko)	1992-08-11
DK0426826T3 (da)	1994-07-04
GR1001407B (el)	1993-11-30
IL94427A (en)	1994-07-31
NO911873L (no)	1991-01-11
CA2187114A1 (en)	1990-11-25
NO180120C (no)	1997-02-19
AU5675890A (en)	1990-12-18
JPH04500219A (ja)	1992-01-16
NO910131D0 (no)	1991-01-11
WO1990014342A1 (en)	1990-11-29
HUT57215A (en)	1991-11-28
JP3042876B2 (ja)	2000-05-22
NO180120B (no)	1996-11-11
IE901748L (en)	1990-11-24
LV10276B (en)	1995-08-20
ES2053195T3 (es)	1994-07-16
EP0426826A1 (en)	1991-05-15
HU205118B (en)	1992-03-30
NO179870B (no)	1996-09-23
CA2032513C (en)	1996-12-17
IE65640B1 (en)	1995-11-15
CA2187114C (en)	2002-03-19
NO910131L (no)	1991-01-11
MD423C2 (ro)	1996-09-30
ATE104968T1 (de)	1994-05-15
EP0426826B1 (en)	1994-04-27
NZ233730A (en)	1992-09-25
CN1039325C (zh)	1998-07-29
IL94427A0 (en)	1991-03-10
PH31619A (en)	1999-01-12
GEP19971047B (en)	1997-11-26
DE69008486T2 (de)	1994-09-15
PT94131B (pt)	1997-01-31
CA2032513A1 (en)	1990-11-25
FI97057B (fi)	1996-06-28
HU905108D0 (en)	1991-07-29
NO911873D0 (no)	1991-05-14
PT94131A (pt)	1991-01-08
NO179870C (no)	1997-01-02
AU631648B2 (en)	1992-12-03
RU2042670C1 (ru)	1995-08-27
LV10276A (lv)	1994-10-20
GR900100397A (en)	1991-10-10
FI97057C (fi)	1996-10-10

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DE2609888A1 (de)	1977-01-20	4,5-epoxy-3-oxo-tetrahydropyran- derivate, deren herstellung und verwendung
DE2065322C3 (de)	1980-03-20	Cycloaliphatisch ungesättigte Epoxyverbindungen und Verfahren zu ihrer Herstellung
DE3216194A1 (de)	1982-11-18	Verfahren zur herstellung des (+)-p-mentha-2,8-dien-1-ols
EP0002743B1 (de)	1981-04-29	Bicyclo (2.2.1)-hept-5-ene(ane)(I), Verfahren zu deren Herstellung, Verwendung von (I) als Riechstoffe und Riechstoffkompositionen mit einem Gehalt an den bicyclischen Verbindungen (I)
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EP0309912B1 (de)	1991-05-15	Verfahren zur Herstellung von alkylierten Dodecahydro-naphtho[2,1-b]-furanen
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DE19731782A1 (de)	1999-01-28	Verfahren zur Herstellung von Pyridylmethylisocyanaten
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EP0131254B1 (de)	1988-05-25	Verfahren zur Herstellung substituierter Tetrahydrofurane
DE1618420C3 (da)	1974-02-28
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