NO313826B1 - Substituerte cykloheptener, deres fremstilling og anvendelse samt legemidler omfattende disse - Google Patents

Substituerte cykloheptener, deres fremstilling og anvendelse samt legemidler omfattende disse Download PDF

Info

Publication number: NO313826B1
Authority: NO; Norway
Prior art keywords: hydrochloride; enyl; cyclohept; phenol; dimethylaminomethyl
Prior art date: 1998-12-14

Application number

NO19996156A

Other languages

English (en)

Norwegian (no)

Other versions

NO996156D0 (no

NO996156L (no

Inventor

Oswald Zimmer

Wolfgang Werner A Strassburger

Werner G Nter Englberger

Babette-Yvonne Koegel

Original Assignee

Gruenenthal Gmbh

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.)

1998-12-14

Filing date

1999-12-13

Publication date

2002-12-09

1999-12-13 Application filed by Gruenenthal Gmbh filed Critical Gruenenthal Gmbh

1999-12-13 Publication of NO996156D0 publication Critical patent/NO996156D0/no

2000-06-15 Publication of NO996156L publication Critical patent/NO996156L/no

2002-12-09 Publication of NO313826B1 publication Critical patent/NO313826B1/no

Links

150000001933 cycloheptenes Chemical class 0.000 title claims description 9
239000003814 drug Substances 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title claims description 5
229940079593 drug Drugs 0.000 title claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 69
150000001875 compounds Chemical class 0.000 claims description 38
-1 3-[4-dimethylaminomethyl-3-(3-hydroxy-phenyl)-cyclohept-3-enyl]-naphth-2-ol Chemical compound 0.000 claims description 16
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
230000000202 analgesic effect Effects 0.000 claims description 5
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
150000003509 tertiary alcohols Chemical class 0.000 claims description 4
VEDLSVHUUANPIM-UHFFFAOYSA-N 2-[4-[(dimethylamino)methyl]-3-(3-hydroxyphenyl)cyclohept-3-en-1-yl]phenol Chemical compound C1CCC(CN(C)C)=C(C=2C=C(O)C=CC=2)CC1C1=CC=CC=C1O VEDLSVHUUANPIM-UHFFFAOYSA-N 0.000 claims description 3
BXWGRTBVCWKXHT-UHFFFAOYSA-N 3-[2-[(dimethylamino)methyl]-6-(3-methylphenyl)cyclohepten-1-yl]phenol Chemical compound C1CCC(CN(C)C)=C(C=2C=C(O)C=CC=2)CC1C1=CC=CC(C)=C1 BXWGRTBVCWKXHT-UHFFFAOYSA-N 0.000 claims description 3
IZFNNKOBHYKMMY-UHFFFAOYSA-N 3-[2-[(dimethylamino)methyl]-6-(4-hydroxyphenyl)cyclohepten-1-yl]phenol Chemical compound C1CCC(CN(C)C)=C(C=2C=C(O)C=CC=2)CC1C1=CC=C(O)C=C1 IZFNNKOBHYKMMY-UHFFFAOYSA-N 0.000 claims description 3
QMZITLVMHJJLGY-UHFFFAOYSA-N 3-[6-(3-tert-butylphenyl)-2-[(dimethylamino)methyl]cyclohepten-1-yl]phenol Chemical compound C1CCC(CN(C)C)=C(C=2C=C(O)C=CC=2)CC1C1=CC=CC(C(C)(C)C)=C1 QMZITLVMHJJLGY-UHFFFAOYSA-N 0.000 claims description 3
DYZJFPMLHCUEIQ-UHFFFAOYSA-N 3-[6-benzyl-2-[(dimethylamino)methyl]cyclohepten-1-yl]phenol Chemical compound C1CCC(CN(C)C)=C(C=2C=C(O)C=CC=2)CC1CC1=CC=CC=C1 DYZJFPMLHCUEIQ-UHFFFAOYSA-N 0.000 claims description 3
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150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
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CLKOFPXJLQSYAH-ABRJDSQDSA-N bacitracin A Chemical compound C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2N=CNC=2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 CLKOFPXJLQSYAH-ABRJDSQDSA-N 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229940098773 bovine serum albumin Drugs 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000872 buffer Substances 0.000 description 1
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201000011510 cancer Diseases 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
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239000003054 catalyst Substances 0.000 description 1
210000001638 cerebellum Anatomy 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229940107137 cholecystokinin Drugs 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
WZCRDVTWUYLPTR-UHFFFAOYSA-N cyclohept-2-en-1-one Chemical compound O=C1CCCCC=C1 WZCRDVTWUYLPTR-UHFFFAOYSA-N 0.000 description 1
CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical class O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
238000006264 debenzylation reaction Methods 0.000 description 1
239000000841 delta opiate receptor agonist Substances 0.000 description 1
238000011161 development Methods 0.000 description 1
125000005105 dialkylarylsilyl group Chemical group 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
150000002148 esters Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
244000144993 groups of animals Species 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
238000000265 homogenisation Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
238000012417 linear regression Methods 0.000 description 1
150000002641 lithium Chemical group 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
239000000463 material Substances 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
210000001767 medulla oblongata Anatomy 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C UZHSEJADLWPNLE-GRGSLBFTSA-N 0.000 description 1
229960004127 naloxone Drugs 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000002981 neuropathic effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000009871 nonspecific binding Effects 0.000 description 1
239000003401 opiate antagonist Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
210000002975 pon Anatomy 0.000 description 1
238000003825 pressing Methods 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
238000012545 processing Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000002407 reforming Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000036280 sedation Effects 0.000 description 1
IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
230000009870 specific binding Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
125000005106 triarylsilyl group Chemical group 0.000 description 1
125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
230000008673 vomiting Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/02—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/16—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a six-membered ring
- C07C13/18—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a six-membered ring with a cyclohexane ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/74—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/64—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Pain & Pain Management (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Rheumatology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Medicinal Preparation (AREA)

NO19996156A 1998-12-14 1999-12-13 Substituerte cykloheptener, deres fremstilling og anvendelse samt legemidler omfattende disse NO313826B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19857475A DE19857475A1 (de)	1998-12-14	1998-12-14	Substituierte Cycloheptene, deren Herstellung und Verwendung

Publications (3)

Publication Number	Publication Date
NO996156D0 NO996156D0 (no)	1999-12-13
NO996156L NO996156L (no)	2000-06-15
NO313826B1 true NO313826B1 (no)	2002-12-09

Family

ID=7890934

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19996156A NO313826B1 (no)	1998-12-14	1999-12-13	Substituerte cykloheptener, deres fremstilling og anvendelse samt legemidler omfattende disse

Country Status (26)

Country	Link
US (1)	US6323369B1 (fr)
EP (1)	EP1010689B1 (fr)
JP (1)	JP4440398B2 (fr)
KR (1)	KR20000048101A (fr)
CN (1)	CN1231457C (fr)
AR (1)	AR021616A1 (fr)
AT (1)	ATE231119T1 (fr)
AU (1)	AU767102B2 (fr)
BR (1)	BR9907340A (fr)
CA (1)	CA2292017C (fr)
CZ (1)	CZ296788B6 (fr)
DE (2)	DE19857475A1 (fr)
DK (1)	DK1010689T3 (fr)
ES (1)	ES2190632T3 (fr)
HU (1)	HU224313B1 (fr)
IL (1)	IL133481A (fr)
NO (1)	NO313826B1 (fr)
NZ (1)	NZ501651A (fr)
PE (1)	PE20001328A1 (fr)
PL (1)	PL199875B1 (fr)
PT (1)	PT1010689E (fr)
RU (1)	RU2233268C2 (fr)
SI (1)	SI1010689T1 (fr)
SK (1)	SK284186B6 (fr)
UY (1)	UY25841A1 (fr)
ZA (1)	ZA997637B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10000312A1 (de)	2000-01-05	2001-07-12	Gruenenthal Gmbh	Substituierte Aminomethyl-Phenyl-Cyclohexanderivate
DE10261091A1 (de)	2002-12-20	2004-07-01	Grünenthal GmbH	Gesättigte und ungesättigte Heteroarylcycloalkylmethyl-Amine
DE10326097A1 (de) *	2003-06-06	2005-01-05	Grünenthal GmbH	Verfahren zur Herstellung von Dimethyl-(3-aryl-butyl)-aminverbindungen
DE102004034619A1 (de) *	2004-07-16	2006-02-23	Grünenthal GmbH	Substituierte Aminoverbindungen als 5-HT/NA Uptakehemmer
CN103965059B (zh) *	2013-02-06	2017-12-22	上海科胜药物研发有限公司	一种制备(1r,2s)‑2‑(3,4‑二氟苯基)环丙胺的方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1518663A1 (de) *	1965-08-02	1969-12-18	Gruenenthal Chemie	Basisch substituierte Cycloalken-derivate und Verfahren zu ihrer Herstellung
US3830934A (en) *	1967-07-27	1974-08-20	Gruenenthal Chemie	Analgesic and antitussive compositions and methods
US4366172A (en) *	1977-09-29	1982-12-28	The Upjohn Company	4-Amino-cyclohexanols, their pharmaceutical compositions and methods of use

1998
- 1998-12-14 DE DE19857475A patent/DE19857475A1/de not_active Ceased
1999
- 1999-11-11 PT PT99122437T patent/PT1010689E/pt unknown
- 1999-11-11 AT AT99122437T patent/ATE231119T1/de active
- 1999-11-11 DK DK99122437T patent/DK1010689T3/da active
- 1999-11-11 SI SI9930229T patent/SI1010689T1/xx unknown
- 1999-11-11 EP EP99122437A patent/EP1010689B1/fr not_active Expired - Lifetime
- 1999-11-11 DE DE59904035T patent/DE59904035D1/de not_active Expired - Lifetime
- 1999-11-11 ES ES99122437T patent/ES2190632T3/es not_active Expired - Lifetime
- 1999-12-03 PE PE1999001207A patent/PE20001328A1/es not_active Application Discontinuation
- 1999-12-08 NZ NZ501651A patent/NZ501651A/xx not_active IP Right Cessation
- 1999-12-09 AU AU64406/99A patent/AU767102B2/en not_active Ceased
- 1999-12-09 UY UY25841A patent/UY25841A1/es not_active Application Discontinuation
- 1999-12-09 AR ARP990106296A patent/AR021616A1/es active IP Right Grant
- 1999-12-10 CA CA002292017A patent/CA2292017C/fr not_active Expired - Fee Related
- 1999-12-13 NO NO19996156A patent/NO313826B1/no unknown
- 1999-12-13 SK SK1742-99A patent/SK284186B6/sk not_active IP Right Cessation
- 1999-12-13 CN CNB991246985A patent/CN1231457C/zh not_active Expired - Fee Related
- 1999-12-13 ZA ZA9907637A patent/ZA997637B/xx unknown
- 1999-12-13 HU HU9904564A patent/HU224313B1/hu not_active IP Right Cessation
- 1999-12-13 KR KR1019990057132A patent/KR20000048101A/ko not_active Withdrawn
- 1999-12-13 CZ CZ0451499A patent/CZ296788B6/cs not_active IP Right Cessation
- 1999-12-13 PL PL337154A patent/PL199875B1/pl not_active IP Right Cessation
- 1999-12-13 JP JP35352499A patent/JP4440398B2/ja not_active Expired - Fee Related
- 1999-12-13 IL IL13348199A patent/IL133481A/en not_active IP Right Cessation
- 1999-12-14 US US09/460,717 patent/US6323369B1/en not_active Expired - Fee Related
- 1999-12-14 BR BR9907340-4A patent/BR9907340A/pt not_active Application Discontinuation
- 1999-12-14 RU RU99126508/04A patent/RU2233268C2/ru not_active IP Right Cessation

Also Published As

Publication number	Publication date
AR021616A1 (es)	2002-07-31
HK1028595A1 (en)	2001-02-23
CN1231457C (zh)	2005-12-14
EP1010689A1 (fr)	2000-06-21
DE59904035D1 (de)	2003-02-20
CA2292017C (fr)	2009-09-08
DE19857475A1 (de)	2000-06-15
CN1266053A (zh)	2000-09-13
UY25841A1 (es)	2000-09-29
AU6440699A (en)	2000-06-15
PT1010689E (pt)	2003-06-30
RU2233268C2 (ru)	2004-07-27
PL337154A1 (en)	2000-06-19
US6323369B1 (en)	2001-11-27
SI1010689T1 (en)	2003-06-30
DK1010689T3 (da)	2003-02-10
CZ451499A3 (cs)	2000-07-12
NO996156D0 (no)	1999-12-13
HU9904564D0 (en)	2000-02-28
ZA997637B (en)	2000-06-14
SK284186B6 (sk)	2004-10-05
PE20001328A1 (es)	2000-12-23
NO996156L (no)	2000-06-15
EP1010689B1 (fr)	2003-01-15
KR20000048101A (ko)	2000-07-25
HUP9904564A3 (en)	2001-01-29
AU767102B2 (en)	2003-10-30
CA2292017A1 (fr)	2000-06-14
IL133481A (en)	2004-05-12
BR9907340A (pt)	2001-01-16
JP4440398B2 (ja)	2010-03-24
NZ501651A (en)	2000-12-22
HU224313B1 (hu)	2005-07-28
SK174299A3 (en)	2000-07-11
HUP9904564A2 (hu)	2000-12-28
PL199875B1 (pl)	2008-11-28
IL133481A0 (en)	2001-04-30
CZ296788B6 (cs)	2006-06-14
JP2000178238A (ja)	2000-06-27
ES2190632T3 (es)	2003-08-01
ATE231119T1 (de)	2003-02-15

Publication	Publication Date	Title
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