IL94427A - Process for the production of delmopinol and new intermediates used in this process - Google Patents

Process for the production of delmopinol and new intermediates used in this process

Info

Publication number: IL94427A
Authority: IL; Israel
Prior art keywords: propylpentyl; propyl; compounds; mixture; compound
Prior art date: 1989-05-24

Application number

IL9442790A

Other languages

English (en)

Hebrew (he)

Other versions

IL94427A0 (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

1990-05-17

Publication date

1994-07-31

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

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

1990-05-17 Application filed by Pharmacia Ab filed Critical Pharmacia Ab

1991-03-10 Publication of IL94427A0 publication Critical patent/IL94427A0/xx

1994-07-31 Publication of IL94427A publication Critical patent/IL94427A/en

Links

239000000543 intermediate Substances 0.000 title claims abstract description 13
238000000034 method Methods 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title claims description 20
QSFOWAYMMZCQNF-UHFFFAOYSA-N delmopinol Chemical compound CCCC(CCC)CCCC1COCCN1CCO QSFOWAYMMZCQNF-UHFFFAOYSA-N 0.000 title claims description 17
229960003854 delmopinol Drugs 0.000 title claims description 14
-1 2-propylpentyl Chemical group 0.000 claims abstract description 32
150000001875 compounds Chemical class 0.000 claims description 28
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 21
230000002829 reductive effect Effects 0.000 claims description 5
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
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
230000002152 alkylating effect Effects 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
239000000203 mixture Substances 0.000 description 31
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 14
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
238000001035 drying Methods 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 9
239000012074 organic phase Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
RLUDGGHEFUDPLJ-UHFFFAOYSA-N 4-propylhept-1-en-4-ol Chemical compound CCCC(O)(CCC)CC=C RLUDGGHEFUDPLJ-UHFFFAOYSA-N 0.000 description 6
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
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
239000012267 brine Substances 0.000 description 6
239000012071 phase Substances 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
238000010992 reflux Methods 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
238000006243 chemical reaction Methods 0.000 description 5
238000001816 cooling Methods 0.000 description 5
150000002546 isoxazolidines Chemical class 0.000 description 5
239000000243 solution Substances 0.000 description 5
CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 4
101150041968 CDC13 gene Proteins 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
150000001336 alkenes Chemical class 0.000 description 4
150000001345 alkine derivatives Chemical class 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
244000309464 bull Species 0.000 description 3
150000002547 isoxazolines Chemical class 0.000 description 3
SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 3
239000007858 starting material Substances 0.000 description 3
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
PHUWAKFNUBADFE-UHFFFAOYSA-N 3-(4-propylheptyl)morpholine Chemical compound CCCC(CCC)CCCC1COCCN1 PHUWAKFNUBADFE-UHFFFAOYSA-N 0.000 description 2
WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 description 2
HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
WVLCITYWJRJQJX-UHFFFAOYSA-N 4-propylhept-1-ene Chemical compound CCCC(CCC)CC=C WVLCITYWJRJQJX-UHFFFAOYSA-N 0.000 description 2
XZAXWRHYIPMZHS-UHFFFAOYSA-N 4-propylhept-1-yne Chemical compound CCCC(CCC)CC#C XZAXWRHYIPMZHS-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 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
UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 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
JYZUFTSYNSOVNI-UHFFFAOYSA-N 1-bromo-4-propylheptane Chemical compound CCCC(CCC)CCCBr JYZUFTSYNSOVNI-UHFFFAOYSA-N 0.000 description 1
MKHGVMIXRPGHOO-UHFFFAOYSA-N 2-(benzenesulfonyl)-3-phenyloxaziridine Chemical compound C=1C=CC=CC=1S(=O)(=O)N1OC1C1=CC=CC=C1 MKHGVMIXRPGHOO-UHFFFAOYSA-N 0.000 description 1
LASHFHLFDRTERB-UHFFFAOYSA-N 2-propylpentan-1-ol Chemical compound CCCC(CO)CCC LASHFHLFDRTERB-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
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
238000006736 Huisgen cycloaddition reaction Methods 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
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 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
125000004122 cyclic group Chemical group 0.000 description 1
238000006298 dechlorination reaction Methods 0.000 description 1
238000006056 electrooxidation reaction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000001030 gas--liquid chromatography Methods 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003112 inhibitor Substances 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
229940101209 mercuric oxide Drugs 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
239000002324 mouth wash Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000002798 polar solvent Substances 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
239000000606 toothpaste Substances 0.000 description 1
238000006257 total synthesis reaction Methods 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)

IL9442790A 1989-05-24 1990-05-17 Process for the production of delmopinol and new intermediates used in this process IL94427A (en)

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 (2)

Publication Number	Publication Date
IL94427A0 IL94427A0 (en)	1991-03-10
IL94427A true IL94427A (en)	1994-07-31

Family

ID=26660511

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9442790A IL94427A (en)	1989-05-24	1990-05-17	Process for the production of delmopinol and new intermediates used in this process

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
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
DD300104A5 (de)	1992-05-21
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

Legal Events

Date	Code	Title
1996-08-04	KB	Patent renewed
1999-12-22	HC	Change of name of proprietor(s)
2004-07-25	KB	Patent renewed
2008-07-09	KB	Patent renewed
2011-04-28	EXP	Patent expired

Publication	Publication Date	Title
IL94427A (en)	1994-07-31	Process for the production of delmopinol and new intermediates used in this process
FR2460299A1 (fr)	1981-01-23	Nouveaux derives du pyrazole et leur application therapeutique
JPH07103114B2 (ja)	1995-11-08	３―アリールオキサゾリジノン誘導体、それらの製造方法及び治療での使用
KR20010052886A (ko)	2001-06-25	모르폴린 유도체의 화학적 합성
NO172846B (no)	1993-06-07	Fremgangsmaate for fremstilling av 7,8-dihalogen-3-metyl-2,3-dihydro-2m-benzoksazinderivater og propoksybenzenderivater for utoevelse av fremgangsmaaten.
US6469164B2 (en)	2002-10-22	Process for the synthesis of (2R, 2-alpha-R)-4-benzyl-2-[1-(3,5-bis (trifluoromethyl)phenyl)ethoxy]-1,4-oxazine-3-one
US5212305A (en)	1993-05-18	Process for preparing delmopinol via the intermediates isoxazolidines and isoxazolines
JP5202326B2 (ja)	2013-06-05	デルモピノールとその誘導体の製造方法
EP1131307B1 (de)	2004-08-25	Verfahren zur herstellung von 2-alkyl- 3-(4,5- dihydroisoxazol- 3-yl)-halogenbenzolen
NO145197B (no)	1981-10-26	Analogifremgangsmaate for fremstilling av terapeutisk aktive morfolinforbindelser
DK150509B (da)	1987-03-16	Analogifremgangsmaade til fremstilling af cis-4-(3-phenyl-2-methyl-propyl)-2,6-dimethylmorpholiner
WO2024023154A1 (en)	2024-02-01	Process
LT3370B (en)	1995-08-25	Method for the preparation of delmopinol and intermediates for the said method
US4150043A (en)	1979-04-17	0-(2,3-Epoxypropyl)-hydroximic acid esters
JPH04169583A (ja)	1992-06-17	フェノチアジン誘導体およびその製造方法
US3248430A (en)	1966-04-26	Novel ethers and process for producing same
DK141818B (da)	1980-06-23	Analogifremgangsmaade til fremstilling af tricykloheptyliden-methyl-aminoalkylethere eller syreadditionssalte deraf
JPH01230567A (ja)	1989-09-14	光学活性エピクロルヒドリンの立体化学反転法
Bastiani et al.	1972	Structural constraints on electrocyclic reactions of unsaturated ketenes. Synthesis and irradiation of 2, 4, 4, 5-tetramethylbicyclo [4.2. 0] octa-1, 5-dien-3-one
JPS5939433B2 (ja)	1984-09-22	新規なるモルホリン誘導体及びその酸付加塩の製造法
JPS6216954B2 (da)	1987-04-15
JPS61155353A (ja)	1986-07-15	β，β−ジフルオロ−γ，δ−不飽和カルボン酸エステル
CS276469B6 (cs)	1992-06-17	Způsob výroby cykloalkanonsulfonamidů
JPS5936635B2 (ja)	1984-09-05	シンキナルモルホリンユウドウタイオヨビソノサンフカエンノセイゾウホウ