CA2600456A1 - Procede de preparation de sels amorphes - Google Patents

Procede de preparation de sels amorphes Download PDF

Info

Publication number: CA2600456A1
Authority: CA; Canada
Prior art keywords: magnesium; omeprazole; esomeprazole; amorphous; solvent
Prior art date: 2005-03-08
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.): Abandoned

Application number

CA002600456A

Other languages

English (en)

Inventor

Vijayabhaskar Bolugoddu

Jaydeepkumar Dahayabhai Lilakar

Purandhar Koilkonda

Ramchandra Reddy Pingili

Amarnath Reddy Lekkala

Venkata Rambabu Kammili

Swarupa Reddy Dudipala

Sharat Pandurang Narasapur

Srinivasa Rao Malina

Ramulu Akula

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.)

Dr Reddys Laboratories Ltd

Dr Reddys Laboratories Inc

Original Assignee

Individual

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.)

2005-03-08

Filing date

2006-03-07

Publication date

2006-09-14

2006-03-07 Application filed by Individual filed Critical Individual

2006-09-14 Publication of CA2600456A1 publication Critical patent/CA2600456A1/fr

Status Abandoned legal-status Critical Current

Links

150000003839 salts Chemical class 0.000 title description 8
238000004519 manufacturing process Methods 0.000 title description 4
229960003117 omeprazole magnesium Drugs 0.000 claims abstract description 47
KWORUUGOSLYAGD-WLHYKHABSA-N magnesium;5-methoxy-2-[(r)-(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazol-1-ide Chemical compound [Mg+2].C([S@@](=O)C=1[N-]C2=CC=C(C=C2N=1)OC)C1=NC=C(C)C(OC)=C1C.C([S@@](=O)C=1[N-]C2=CC=C(C=C2N=1)OC)C1=NC=C(C)C(OC)=C1C KWORUUGOSLYAGD-WLHYKHABSA-N 0.000 claims abstract description 44
229960000197 esomeprazole magnesium Drugs 0.000 claims abstract description 43
MQEUGMWHWPYFDD-UHFFFAOYSA-N magnesium;6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1h-benzimidazole Chemical compound [Mg].N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C MQEUGMWHWPYFDD-UHFFFAOYSA-N 0.000 claims abstract description 42
238000001704 evaporation Methods 0.000 claims abstract description 26
230000008020 evaporation Effects 0.000 claims abstract description 21
239000007787 solid Substances 0.000 claims abstract description 21
239000010409 thin film Substances 0.000 claims abstract description 7
238000000034 method Methods 0.000 claims description 61
SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 claims description 44
238000001035 drying Methods 0.000 claims description 39
229960000381 omeprazole Drugs 0.000 claims description 39
239000002904 solvent Substances 0.000 claims description 35
SUBDBMMJDZJVOS-DEOSSOPVSA-N esomeprazole Chemical compound C([S@](=O)C1=NC2=CC=C(C=C2N1)OC)C1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-DEOSSOPVSA-N 0.000 claims description 27
239000002245 particle Substances 0.000 claims description 27
229960004770 esomeprazole Drugs 0.000 claims description 26
239000013557 residual solvent Substances 0.000 claims description 17
239000011777 magnesium Substances 0.000 claims description 9
229910052749 magnesium Inorganic materials 0.000 claims description 8
239000000706 filtrate Substances 0.000 claims description 7
-1 magnesium alkoxide Chemical class 0.000 claims description 7
239000002002 slurry Substances 0.000 claims description 6
238000001914 filtration Methods 0.000 claims description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
239000012298 atmosphere Substances 0.000 claims description 3
238000010951 particle size reduction Methods 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
239000000047 product Substances 0.000 description 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
159000000003 magnesium salts Chemical class 0.000 description 23
230000008569 process Effects 0.000 description 18
239000000203 mixture Substances 0.000 description 14
150000001875 compounds Chemical class 0.000 description 13
239000000463 material Substances 0.000 description 13
238000003801 milling Methods 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
238000000634 powder X-ray diffraction Methods 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
238000010079 rubber tapping Methods 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
238000000862 absorption spectrum Methods 0.000 description 4
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
238000001694 spray drying Methods 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
238000001938 differential scanning calorimetry curve Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
239000000843 powder Substances 0.000 description 3
230000002035 prolonged effect Effects 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
239000013078 crystal Substances 0.000 description 2
150000004683 dihydrates Chemical group 0.000 description 2
238000009826 distribution Methods 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
238000007711 solidification Methods 0.000 description 2
230000008023 solidification Effects 0.000 description 2
239000007921 spray Substances 0.000 description 2
SUBDBMMJDZJVOS-XMMPIXPASA-N (R)-omeprazole Chemical compound C([S@@](=O)C=1NC2=CC=C(C=C2N=1)OC)C1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-XMMPIXPASA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
229910002483 Cu Ka Inorganic materials 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
238000003109 Karl Fischer titration Methods 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
208000007107 Stomach Ulcer Diseases 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
206010057040 Temperature intolerance Diseases 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000009471 action Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
230000008901 benefit Effects 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
230000008859 change Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000008395 clarifying agent Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
235000009508 confectionery Nutrition 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000010908 decantation Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
239000007950 delayed release tablet Substances 0.000 description 1
238000000113 differential scanning calorimetry Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000000718 duodenal ulcer Diseases 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
210000004211 gastric acid Anatomy 0.000 description 1
208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000008543 heat sensitivity Effects 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000010902 jet-milling Methods 0.000 description 1
UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
239000011654 magnesium acetate Substances 0.000 description 1
235000011285 magnesium acetate Nutrition 0.000 description 1
229940069446 magnesium acetate Drugs 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
MQEUGMWHWPYFDD-JIDHJSLPSA-N magnesium;6-methoxy-2-[(s)-(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1h-benzimidazole Chemical compound [Mg].C([S@](=O)C1=NC2=CC=C(C=C2N1)OC)C1=NC=C(C)C(OC)=C1C MQEUGMWHWPYFDD-JIDHJSLPSA-N 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
239000012528 membrane Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
230000036470 plasma concentration Effects 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
229940059096 powder for oral suspension Drugs 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002028 premature Effects 0.000 description 1
229940089505 prilosec Drugs 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000012453 solvate Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
150000004684 trihydrates Chemical group 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)

CA002600456A 2005-03-08 2006-03-07 Procede de preparation de sels amorphes Abandoned CA2600456A1 (fr)

Applications Claiming Priority (7)

Application Number	Priority Date	Filing Date	Title
IN227CH2005		2005-03-08
IN227/CHE/2005		2005-03-08
US67314205P	2005-04-20	2005-04-20
US60/673,142		2005-04-20
IN1543CH2005		2005-10-25
IN1543/CHE/2005		2005-10-25
PCT/US2006/008064 WO2006096709A2 (fr)	2005-03-08	2006-03-07	Procede de preparation de sels amorphes

Publications (1)

Publication Number	Publication Date
CA2600456A1 true CA2600456A1 (fr)	2006-09-14

Family

ID=36953969

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002600456A Abandoned CA2600456A1 (fr)	2005-03-08	2006-03-07	Procede de preparation de sels amorphes

Country Status (3)

Country	Link
EP (1)	EP1856101A4 (fr)
CA (1)	CA2600456A1 (fr)
WO (1)	WO2006096709A2 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7553857B2 (en) *	2005-12-23	2009-06-30	Lek Pharmaceuticals D.D.	S-omeprazole magnesium
ES2532854T3 (es)	2007-02-21	2015-04-01	Cipla Limited	Proceso para la preparación de esomeprazol magnésico dihidrato
EP2147918A1 (fr)	2008-07-21	2010-01-27	LEK Pharmaceuticals D.D.	Procédé de préparation de magnésium d'oméprazole S dans une forme stable
FR2959509B1 (fr)	2010-05-03	2012-07-13	Prod Chim Auxiliaires Et De Synthese	Phase precurseur et son utilisation pour preparer le sel de magnesium tetrahydrate d'un enantiomere d'omeprazole

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2290893C (fr) *	1999-11-16	2007-05-01	Bernard Charles Sherman	Omeprazole de magnesium
US20030212274A1 (en) *	2000-05-15	2003-11-13	Bakthavathsalan Vijayaraghavan	Novel amorphous form of omeprazole salts
US6894066B2 (en) *	2002-05-09	2005-05-17	Bernard Charles Sherman	Magnesium salt of S-omeprazole
WO2004037253A1 (fr) *	2002-10-22	2004-05-06	Ranbaxy Laboratories Limited	Forme amorphe de sels d'esomeprazole

2006
- 2006-03-07 CA CA002600456A patent/CA2600456A1/fr not_active Abandoned
- 2006-03-07 EP EP06737257A patent/EP1856101A4/fr not_active Withdrawn
- 2006-03-07 WO PCT/US2006/008064 patent/WO2006096709A2/fr active Application Filing

Also Published As

Publication number	Publication date
WO2006096709A3 (fr)	2006-12-21
EP1856101A4 (fr)	2009-10-21
EP1856101A2 (fr)	2007-11-21
WO2006096709B1 (fr)	2007-01-18
WO2006096709A2 (fr)	2006-09-14

Legal Events

Date	Code	Title	Description
2012-03-07	FZDE	Discontinued

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