NO326878B1 - Anvendelse av morfolinol - Google Patents

Anvendelse av morfolinol Download PDF

Info

Publication number: NO326878B1
Authority: NO; Norway
Prior art keywords: morpholinol; chlorophenyl; formula; compound; trimethyl
Prior art date: 1998-01-21

Application number

NO20003721A

Other languages

English (en)

Norwegian (no)

Other versions

NO20003721D0 (no

NO20003721L (no

Inventor

David Lee Musso

Phillip Frederick Morgan

John Joseph Partidge

Original Assignee

Glaxo Group Ltd

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.)

1998-01-21

Filing date

2000-07-20

Publication date

2009-03-09

1998-01-21 Priority claimed from GBGB9801230.5A external-priority patent/GB9801230D0/en

2000-07-20 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2000-07-20 Publication of NO20003721D0 publication Critical patent/NO20003721D0/no

2000-09-19 Publication of NO20003721L publication Critical patent/NO20003721L/no

2009-03-09 Publication of NO326878B1 publication Critical patent/NO326878B1/no

Links

OURXRFYZEOUCRM-UHFFFAOYSA-N 4-hydroxymorpholine Chemical compound ON1CCOCC1 OURXRFYZEOUCRM-UHFFFAOYSA-N 0.000 title description 12
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150000003839 salts Chemical class 0.000 claims abstract description 8
RCOBKSKAZMVBHT-TVQRCGJNSA-N radafaxine Chemical compound C[C@@H]1NC(C)(C)CO[C@@]1(O)C1=CC=CC(Cl)=C1 RCOBKSKAZMVBHT-TVQRCGJNSA-N 0.000 claims abstract description 7
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SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 abstract description 6
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MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 15
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230000004060 metabolic process Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
229960001344 methylphenidate Drugs 0.000 description 1
230000003278 mimic effect Effects 0.000 description 1
230000009456 molecular mechanism Effects 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
210000001577 neostriatum Anatomy 0.000 description 1
230000003982 neuronal uptake Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
XXPANQJNYNUNES-UHFFFAOYSA-N nomifensine Chemical compound C12=CC=CC(N)=C2CN(C)CC1C1=CC=CC=C1 XXPANQJNYNUNES-UHFFFAOYSA-N 0.000 description 1
229960001073 nomifensine Drugs 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229940053544 other antidepressants in atc Drugs 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
235000010603 pastilles Nutrition 0.000 description 1
230000037361 pathway Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
YPDVTKJXVHYWFY-UHFFFAOYSA-N phosphoric acid;n'-propan-2-ylpyridine-4-carbohydrazide Chemical compound OP(O)(O)=O.CC(C)NNC(=O)C1=CC=NC=C1 YPDVTKJXVHYWFY-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
230000036470 plasma concentration Effects 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
238000011002 quantification Methods 0.000 description 1
230000005855 radiation Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000012552 review Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
230000005586 smoking cessation Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
241000894007 species Species 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
210000000225 synapse Anatomy 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
235000019505 tobacco product Nutrition 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
239000003029 tricyclic antidepressant agent Substances 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
238000005406 washing Methods 0.000 description 1
230000004580 weight loss Effects 0.000 description 1
229940018503 zyban Drugs 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents

Landscapes

Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Addiction (AREA)
Epidemiology (AREA)
Pain & Pain Management (AREA)
Psychology (AREA)
Endocrinology (AREA)
Hospice & Palliative Care (AREA)
Reproductive Health (AREA)
Child & Adolescent Psychology (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO20003721A 1998-01-21 2000-07-20 Anvendelse av morfolinol NO326878B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GBGB9801230.5A GB9801230D0 (en)	1998-01-21	1998-01-21	Pharmaceutically active morpholinol
US7218098P	1998-01-22	1998-01-22
PCT/US1999/001134 WO1999037305A1 (en)	1998-01-21	1999-01-20	Pharmaceutically active morpholinol

Publications (3)

Publication Number	Publication Date
NO20003721D0 NO20003721D0 (no)	2000-07-20
NO20003721L NO20003721L (no)	2000-09-19
NO326878B1 true NO326878B1 (no)	2009-03-09

Family

ID=26312986

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NO20003721A NO326878B1 (no)	1998-01-21	2000-07-20	Anvendelse av morfolinol
NO20083529A NO20083529L (no)	1998-01-21	2008-08-14	Farmasoytisk aktivt morfolinol

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NO20083529A NO20083529L (no)	1998-01-21	2008-08-14	Farmasoytisk aktivt morfolinol

Country Status (30)

Country	Link
US (2)	US6274579B1 (zh)
EP (2)	EP1829544A1 (zh)
JP (1)	JP2002501025A (zh)
KR (1)	KR100568063B1 (zh)
CN (2)	CN1255389C (zh)
AP (1)	AP1229A (zh)
AT (1)	ATE365042T1 (zh)
AU (1)	AU755536B2 (zh)
BR (1)	BR9907203A (zh)
CA (1)	CA2318268A1 (zh)
CY (1)	CY1106828T1 (zh)
DE (1)	DE69936335T2 (zh)
DK (1)	DK1047428T3 (zh)
EA (1)	EA002410B1 (zh)
EE (1)	EE04452B1 (zh)
ES (1)	ES2288012T3 (zh)
HR (2)	HRP20000494B1 (zh)
HU (1)	HUP0100900A3 (zh)
ID (1)	ID26334A (zh)
IL (2)	IL161942A0 (zh)
IS (1)	IS2494B (zh)
NO (2)	NO326878B1 (zh)
NZ (3)	NZ529316A (zh)
PL (1)	PL193622B1 (zh)
PT (1)	PT1047428E (zh)
SG (1)	SG115489A1 (zh)
SK (1)	SK10912000A3 (zh)
TR (1)	TR200002126T2 (zh)
WO (1)	WO1999037305A1 (zh)
YU (1)	YU67102A (zh)

Families Citing this family (42)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7098206B2 (en) *	1998-01-21	2006-08-29	Smithkline Beecham Corporation	Pharmaceutically active morpholinol
US6998400B2 (en) *	1998-01-22	2006-02-14	Smithkline Beecham Corporation	Pharmaceutically active morpholinol
AU2349999A (en)	1998-01-29	1999-08-16	Sepracor, Inc.	Pharmacological uses of pure (+) -bupropion
JP2002501892A (ja)	1998-01-29	2002-01-22	セプラコアインコーポレーテッド	光学的に純粋な（−）−ビュープロピオンの薬学的使用
US6734213B2 (en)	1999-01-20	2004-05-11	Smithkline Beecham Corporation	Pharmaceutically active morpholinol
US6855820B2 (en)	1999-01-20	2005-02-15	Smithkline Beecham Corporation	Pharmaceutically active morpholinol
US6337328B1 (en) *	1999-03-01	2002-01-08	Sepracor, Inc.	Bupropion metabolites and methods of use
US6342496B1 (en)	1999-03-01	2002-01-29	Sepracor Inc.	Bupropion metabolites and methods of use
AU7750100A (en) *	1999-10-13	2001-04-23	Glaxo Group Limited	Method for the treatment of obesity
GB0003232D0 (en) *	2000-02-11	2000-04-05	Smithkline Beecham Plc	Novel composition
US7145649B2 (en) *	2000-12-21	2006-12-05	Brasscorp Limited	Method of producing an ultra-violet or near ultra-violet light source for non-destructive inspection or testing
US6979104B2 (en)	2001-12-31	2005-12-27	R.J. Doran & Co. LTD	LED inspection lamp
US20050215552A1 (en) *	2002-05-17	2005-09-29	Gadde Kishore M	Method for treating obesity
MXPA04011203A (es)	2002-05-17	2005-07-14	Univ Duke	Metodo para tratar la obesidad.
US7384941B2 (en) *	2002-08-23	2008-06-10	Eli Lilly And Company	2-(phenoxymethyl)-and 2-(phenylthiomethyl)-morpholine derivatives for use as selective norepinephrine reuptake inhibitors
GB0219687D0 (en) *	2002-08-23	2002-10-02	Lilly Co Eli	Benzyl morpholine derivatives
EP2316456B1 (en)	2003-04-29	2017-06-14	Orexigen Therapeutics, Inc.	Compositions for affecting weight loss comprising an opioid antagonist and bupropion
JP2007509855A (ja) *	2003-10-27	2007-04-19	スミスクラインビーチャムコーポレーション	（＋）−（２ｓ，３ｓ）−２−（３−クロロフェニル）−３，５，５−トリメチル−２−モルホリノール、その塩および溶媒和物を調製するためのジアステレオマー動的速度論分割プロセス
GB0325055D0 (en) *	2003-10-27	2003-12-03	Smithkline Beecham Corp	New process
GB0326148D0 (en) *	2003-11-10	2003-12-17	Lilly Co Eli	Morpholine derivatives
GB0327195D0 (en) *	2003-11-21	2003-12-24	Smithkline Beecham Corp	Novel use
GB0327619D0 (en) *	2003-11-27	2003-12-31	Smithkline Beecham Corp	New use
US7713959B2 (en) *	2004-01-13	2010-05-11	Duke University	Compositions of an anticonvulsant and mirtazapine to prevent weight gain
CA2553207A1 (en) *	2004-01-13	2005-08-04	Kishore M. Gadde	Compositions of an anticonvulsant and an antipsychotic drug for affecting weight loss
JP2007536229A (ja) *	2004-05-03	2007-12-13	デューク・ユニバーシティー	体重減少に作用するための組成物
FI117283B (fi)	2005-02-04	2006-08-31	Kone Corp	Hissijärjestelmä
WO2007067341A2 (en)	2005-11-22	2007-06-14	Orexigen Therapeutics, Inc.	Compositions and methods for increasing insulin sensitivity
US7763612B2 (en) *	2006-01-03	2010-07-27	Algebra, Inc.	Therapeutic amine-arylsulfonamide conjugate compounds
US8916195B2 (en)	2006-06-05	2014-12-23	Orexigen Therapeutics, Inc.	Sustained release formulation of naltrexone
KR101479324B1 (ko)	2006-11-09	2015-01-05	오렉시젠 세러퓨틱스 인크.	신속하게 용해되는 중간층을 포함하는 층상의 약제학적 제형
MX343867B (es)	2006-11-09	2016-11-25	Orexigen Therapeutics Inc	Paquete de dosificacion unitaria y metodos para administrar medicaciones de perdida de peso.
US20090075994A1 (en) *	2007-09-14	2009-03-19	Protia, Llc	Deuterium-enriched radafaxine
CA2725930A1 (en)	2008-05-30	2009-12-30	Orexigen Therapeutics, Inc.	Methods for treating visceral fat conditions
CA2758774C (en)	2009-04-15	2015-02-03	Research Triangle Institute	Monoamine reuptake inhibitors
US9248123B2 (en)	2010-01-11	2016-02-02	Orexigen Therapeutics, Inc.	Methods of providing weight loss therapy in patients with major depression
JP5952267B2 (ja)	2010-05-21	2016-07-13	リサーチ・トライアングル・インスティチュート	薬物依存を処置するためのヒドロキシブプロピオン類似体（政府支援研究または開発）
CA2800220C (en)	2010-05-21	2019-04-30	Research Triangle Institute	Phenylmorpholines and analogues thereof
US9510405B2 (en)	2011-06-30	2016-11-29	Schneider Electric Industries Sas	Dual power SMPS for a modular lighting system
CN102670617B (zh) *	2012-04-13	2013-03-20	湖南大学	布洛芬2-（2-芳基吗啉-4-基）乙酯作为制备抗抑郁药物的应用
AU2013271622B2 (en)	2012-06-06	2018-03-01	Nalpropion Pharmaceuticals Llc	Methods of treating overweight and obesity
CN105949142B (zh) *	2016-05-21	2018-03-27	南华大学	具有抗抑郁活性的单一手性化合物及其制备方法和应用
RU2763728C1 (ru) *	2021-06-17	2021-12-30	Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" (ПГНИУ)	Применение 3-(2-(4-нитрофенил)-2-оксоэтилиден)морфолин-2-она в качестве средства, обладающего противомикробной активностью

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US170430A (en) *		1875-11-30		Improvement in furnaces for heating steel in tempering
GB8417170D0 (en) *	1984-07-05	1984-08-08	Wellcome Found	Heterocyclic pharmaceutical compounds
GB9108629D0 (en)	1991-04-23	1991-06-12	Wellcome Found	Heterocyclic pharmaceutical compounds,preparation and use
US6337328B1 (en)	1999-03-01	2002-01-08	Sepracor, Inc.	Bupropion metabolites and methods of use

1999
- 1999-01-20 EP EP07110283A patent/EP1829544A1/en not_active Withdrawn
- 1999-01-20 NZ NZ529316A patent/NZ529316A/en unknown
- 1999-01-20 CN CNB2004100085595A patent/CN1255389C/zh not_active Expired - Fee Related
- 1999-01-20 ES ES99903200T patent/ES2288012T3/es not_active Expired - Lifetime
- 1999-01-20 BR BR9907203-3A patent/BR9907203A/pt not_active Application Discontinuation
- 1999-01-20 HU HU0100900A patent/HUP0100900A3/hu unknown
- 1999-01-20 NZ NZ505809A patent/NZ505809A/xx unknown
- 1999-01-20 PL PL99342012A patent/PL193622B1/pl not_active IP Right Cessation
- 1999-01-20 SG SG200204411A patent/SG115489A1/en unknown
- 1999-01-20 TR TR2000/02126T patent/TR200002126T2/xx unknown
- 1999-01-20 AT AT99903200T patent/ATE365042T1/de active
- 1999-01-20 CA CA002318268A patent/CA2318268A1/en not_active Abandoned
- 1999-01-20 PT PT99903200T patent/PT1047428E/pt unknown
- 1999-01-20 JP JP2000528287A patent/JP2002501025A/ja active Pending
- 1999-01-20 IL IL16194299A patent/IL161942A0/xx unknown
- 1999-01-20 WO PCT/US1999/001134 patent/WO1999037305A1/en active IP Right Grant
- 1999-01-20 AU AU23280/99A patent/AU755536B2/en not_active Ceased
- 1999-01-20 ID IDW20001597A patent/ID26334A/id unknown
- 1999-01-20 KR KR1020007007996A patent/KR100568063B1/ko not_active IP Right Cessation
- 1999-01-20 EP EP99903200A patent/EP1047428B1/en not_active Expired - Lifetime
- 1999-01-20 DE DE69936335T patent/DE69936335T2/de not_active Expired - Lifetime
- 1999-01-20 CN CNB998042706A patent/CN1203858C/zh not_active Expired - Fee Related
- 1999-01-20 IL IL13734699A patent/IL137346A0/xx not_active IP Right Cessation
- 1999-01-20 AP APAP/P/2000/001869A patent/AP1229A/en active
- 1999-01-20 EE EEP200000438A patent/EE04452B1/xx not_active IP Right Cessation
- 1999-01-20 NZ NZ520349A patent/NZ520349A/en unknown
- 1999-01-20 SK SK1091-2000A patent/SK10912000A3/sk unknown
- 1999-01-20 US US09/233,531 patent/US6274579B1/en not_active Expired - Fee Related
- 1999-01-20 EA EA200000691A patent/EA002410B1/ru not_active IP Right Cessation
- 1999-01-20 DK DK99903200T patent/DK1047428T3/da active
2000
- 2000-07-20 IS IS5568A patent/IS2494B/is unknown
- 2000-07-20 NO NO20003721A patent/NO326878B1/no not_active IP Right Cessation
- 2000-07-21 HR HR20000494A patent/HRP20000494B1/xx not_active IP Right Cessation
2001
- 2001-06-22 US US09/886,391 patent/US6391875B2/en not_active Expired - Fee Related
2002
- 2002-09-06 YU YU67102A patent/YU67102A/sh unknown
2005
- 2005-12-29 HR HR20051024A patent/HRP20051024A2/hr not_active Application Discontinuation
2007
- 2007-08-31 CY CY20071101117T patent/CY1106828T1/el unknown
2008
- 2008-08-14 NO NO20083529A patent/NO20083529L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
KR20010034285A (ko)	2001-04-25
YU67102A (sh)	2004-12-31
AU755536B2 (en)	2002-12-12
CA2318268A1 (en)	1999-07-29
IS2494B (is)	2009-02-15
PL193622B1 (pl)	2007-02-28
ATE365042T1 (de)	2007-07-15
CY1106828T1 (el)	2012-05-23
NO20003721D0 (no)	2000-07-20
EP1047428B1 (en)	2007-06-20
DE69936335T2 (de)	2008-02-28
HRP20000494B1 (en)	2009-02-28
NZ505809A (en)	2002-09-27
AU2328099A (en)	1999-08-09
CN1528753A (zh)	2004-09-15
IL137346A0 (en)	2001-07-24
US6391875B2 (en)	2002-05-21
CN1294513A (zh)	2001-05-09
NO20003721L (no)	2000-09-19
TR200002126T2 (tr)	2000-12-21
EA200000691A1 (ru)	2001-04-23
US6274579B1 (en)	2001-08-14
NZ529316A (en)	2004-05-28
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