SK102798A3 - Azabicyclic esters of carbamic acids useful in therapy - Google Patents
Azabicyclic esters of carbamic acids useful in therapy Download PDFInfo
- Publication number
- SK102798A3 SK102798A3 SK1027-98A SK102798A SK102798A3 SK 102798 A3 SK102798 A3 SK 102798A3 SK 102798 A SK102798 A SK 102798A SK 102798 A3 SK102798 A3 SK 102798A3
- Authority
- SK
- Slovakia
- Prior art keywords
- formula
- azabicyclo
- compound
- ester
- octan
- Prior art date
Links
- 238000002560 therapeutic procedure Methods 0.000 title abstract description 4
- 150000002148 esters Chemical class 0.000 title description 13
- 150000001715 carbamic acids Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 107
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 24
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 21
- 150000002367 halogens Chemical group 0.000 claims abstract description 21
- 238000011282 treatment Methods 0.000 claims abstract description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 16
- -1 -OR5 Chemical group 0.000 claims abstract description 15
- 238000011321 prophylaxis Methods 0.000 claims abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 125000001424 substituent group Chemical group 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
- 230000008569 process Effects 0.000 claims abstract description 6
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 21
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 12
- 208000035475 disorder Diseases 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 12
- 239000012442 inert solvent Substances 0.000 claims description 11
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- 238000002360 preparation method Methods 0.000 claims description 7
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 6
- 229910000085 borane Inorganic materials 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 229960002715 nicotine Drugs 0.000 claims description 6
- JRNNBGOEDTYSGH-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-(3,4-dichlorophenyl)carbamate Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=O)OC1C(CC2)CCN2C1 JRNNBGOEDTYSGH-UHFFFAOYSA-N 0.000 claims description 5
- SLJMPDGIEKZJAU-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-(4-bromophenyl)carbamate Chemical compound C1=CC(Br)=CC=C1NC(=O)OC1C(CC2)CCN2C1 SLJMPDGIEKZJAU-UHFFFAOYSA-N 0.000 claims description 5
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- 239000012948 isocyanate Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 4
- WVQQNNNYMPFHGO-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-(4-methylphenyl)carbamate Chemical compound C1=CC(C)=CC=C1NC(=O)OC1C(CC2)CCN2C1 WVQQNNNYMPFHGO-UHFFFAOYSA-N 0.000 claims description 4
- JEPJAGMRBZWMCT-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-phenylcarbamate Chemical compound C1N(CC2)CCC2C1OC(=O)NC1=CC=CC=C1 JEPJAGMRBZWMCT-UHFFFAOYSA-N 0.000 claims description 4
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- 230000005586 smoking cessation Effects 0.000 claims description 4
- ONHFLIBNUOFXHA-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-(3-methoxyphenyl)carbamate Chemical compound COC1=CC=CC(NC(=O)OC2C3CCN(CC3)C2)=C1 ONHFLIBNUOFXHA-UHFFFAOYSA-N 0.000 claims description 3
- PPPJULCFKXODES-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-(4-cyanophenyl)carbamate Chemical compound C1N(CC2)CCC2C1OC(=O)NC1=CC=C(C#N)C=C1 PPPJULCFKXODES-UHFFFAOYSA-N 0.000 claims description 3
- SSLDFEPTWKCCLA-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-(4-methoxyphenyl)carbamate Chemical compound C1=CC(OC)=CC=C1NC(=O)OC1C(CC2)CCN2C1 SSLDFEPTWKCCLA-UHFFFAOYSA-N 0.000 claims description 3
- NBDVCMQUQDOFRR-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-naphthalen-1-ylcarbamate Chemical compound C1N(CC2)CCC2C1OC(=O)NC1=CC=CC2=CC=CC=C12 NBDVCMQUQDOFRR-UHFFFAOYSA-N 0.000 claims description 3
- RYDWZFYEYKGKQN-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-pyridin-2-ylcarbamate Chemical compound C1N(CC2)CCC2C1OC(=O)NC1=CC=CC=N1 RYDWZFYEYKGKQN-UHFFFAOYSA-N 0.000 claims description 3
- SOGRRKOWZXEBMI-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-quinolin-3-ylcarbamate Chemical compound C1N(CC2)CCC2C1OC(=O)NC1=CN=C(C=CC=C2)C2=C1 SOGRRKOWZXEBMI-UHFFFAOYSA-N 0.000 claims description 3
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- JEPJAGMRBZWMCT-ZDUSSCGKSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] n-phenylcarbamate Chemical compound O([C@@H]1C2CCN(CC2)C1)C(=O)NC1=CC=CC=C1 JEPJAGMRBZWMCT-ZDUSSCGKSA-N 0.000 claims description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 3
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 208000028683 bipolar I disease Diseases 0.000 claims description 3
- 230000001713 cholinergic effect Effects 0.000 claims description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims description 3
- 201000003723 learning disability Diseases 0.000 claims description 3
- 230000006984 memory degeneration Effects 0.000 claims description 3
- 208000023060 memory loss Diseases 0.000 claims description 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 3
- OVPWBKSJYFYQPC-UHFFFAOYSA-N o-(1-azabicyclo[2.2.2]octan-3-yl) n-phenylcarbamothioate Chemical compound C1N(CC2)CCC2C1OC(=S)NC1=CC=CC=C1 OVPWBKSJYFYQPC-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 230000009471 action Effects 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
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- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 claims 1
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- 125000004093 cyano group Chemical group *C#N 0.000 abstract 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 239000007787 solid Substances 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
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- IVLICPVPXWEGCA-UHFFFAOYSA-N 3-quinuclidinol Chemical compound C1C[C@@H]2C(O)C[N@]1CC2 IVLICPVPXWEGCA-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
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- 239000000243 solution Substances 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 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 8
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- 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 4
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- RAJYWSMRWRODFV-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl carbamate Chemical class C1CC2C(OC(=O)N)CN1CC2 RAJYWSMRWRODFV-UHFFFAOYSA-N 0.000 description 3
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- ULHIMEHJZGFPKJ-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-(2-fluorophenyl)carbamate Chemical compound FC1=CC=CC=C1NC(=O)OC1C(CC2)CCN2C1 ULHIMEHJZGFPKJ-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- A61P25/14—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
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- 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
- A61P25/22—Anxiolytics
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9600683A SE9600683D0 (sv) | 1996-02-23 | 1996-02-23 | Azabicyclic esters of carbamic acids useful in therapy |
| PCT/SE1997/000294 WO1997030998A1 (en) | 1996-02-23 | 1997-02-21 | Azabicyclic esters of carbamic acids useful in therapy |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK102798A3 true SK102798A3 (en) | 1999-01-11 |
Family
ID=20401517
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1027-98A SK102798A3 (en) | 1996-02-23 | 1997-02-21 | Azabicyclic esters of carbamic acids useful in therapy |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US5998429A (enExample) |
| EP (1) | EP0885221B1 (enExample) |
| JP (1) | JP2000505452A (enExample) |
| KR (1) | KR19990087184A (enExample) |
| CN (1) | CN1063749C (enExample) |
| AR (1) | AR005876A1 (enExample) |
| AT (1) | ATE219081T1 (enExample) |
| AU (1) | AU706944B2 (enExample) |
| BR (1) | BR9707616A (enExample) |
| CA (1) | CA2246051A1 (enExample) |
| CZ (1) | CZ289110B6 (enExample) |
| DE (1) | DE69713295T2 (enExample) |
| EE (1) | EE9800250A (enExample) |
| HU (1) | HUP9901273A3 (enExample) |
| ID (1) | ID15969A (enExample) |
| IL (2) | IL125620A (enExample) |
| IS (1) | IS4830A (enExample) |
| NO (1) | NO983711L (enExample) |
| NZ (1) | NZ331145A (enExample) |
| PL (1) | PL328614A1 (enExample) |
| RU (1) | RU2172739C2 (enExample) |
| SE (1) | SE9600683D0 (enExample) |
| SK (1) | SK102798A3 (enExample) |
| TR (1) | TR199801642T2 (enExample) |
| WO (1) | WO1997030998A1 (enExample) |
| ZA (1) | ZA971082B (enExample) |
Families Citing this family (131)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US5977144A (en) * | 1992-08-31 | 1999-11-02 | University Of Florida | Methods of use and compositions for benzylidene- and cinnamylidene-anabaseines |
| US7214686B2 (en) | 1997-06-30 | 2007-05-08 | Targacept, Inc. | Pharmaceutical compositions and methods for effecting dopamine release |
| US6632823B1 (en) * | 1997-12-22 | 2003-10-14 | Merck & Co., Inc. | Substituted pyridine compounds useful as modulators of acetylcholine receptors |
| US6277870B1 (en) | 1998-05-04 | 2001-08-21 | Astra Ab | Use |
| FR2804430B1 (fr) * | 2000-01-28 | 2002-03-22 | Sanofi Synthelabo | Derives de 4-heteroaryl-1,4-diazabicyclo[3.2.2] nonane, leur preparation et leur application en therapeutique |
| GB0010955D0 (en) | 2000-05-05 | 2000-06-28 | Novartis Ag | Organic compounds |
| US8914114B2 (en) | 2000-05-23 | 2014-12-16 | The Feinstein Institute For Medical Research | Inhibition of inflammatory cytokine production by cholinergic agonists and vagus nerve stimulation |
| AU2001284645A1 (en) * | 2000-08-18 | 2002-03-04 | Pharmacia And Upjohn Company | Quinuclidine-substituted aryl compounds for treatment of disease |
| US6486172B2 (en) | 2000-08-18 | 2002-11-26 | Pharmacia & Upjohn Company | Quinuclidine-substituted aryl compounds for treatment of disease |
| EP1381603A2 (en) * | 2000-08-18 | 2004-01-21 | PHARMACIA & UPJOHN COMPANY | Quinuclidine-substituedaryl moieties for treatment of disease ( nicotinic acetylcholine receptor ligands ) |
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- 1997-02-21 HU HU9901273A patent/HUP9901273A3/hu unknown
- 1997-02-21 AU AU22387/97A patent/AU706944B2/en not_active Ceased
- 1997-02-21 SK SK1027-98A patent/SK102798A3/sk unknown
- 1997-02-21 EP EP97905544A patent/EP0885221B1/en not_active Expired - Lifetime
- 1997-02-21 TR TR1998/01642T patent/TR199801642T2/xx unknown
- 1997-02-21 KR KR1019980706579A patent/KR19990087184A/ko not_active Withdrawn
- 1997-02-21 RU RU98117804A patent/RU2172739C2/ru active
- 1997-02-21 PL PL97328614A patent/PL328614A1/xx unknown
- 1997-02-21 CZ CZ19982659A patent/CZ289110B6/cs not_active IP Right Cessation
- 1997-02-21 NZ NZ331145A patent/NZ331145A/en unknown
- 1997-02-21 IL IL12562097A patent/IL125620A/en not_active IP Right Cessation
- 1997-02-21 DE DE69713295T patent/DE69713295T2/de not_active Expired - Fee Related
- 1997-02-21 US US08/836,143 patent/US5998429A/en not_active Expired - Fee Related
- 1997-02-21 EE EE9800250A patent/EE9800250A/xx unknown
- 1997-02-21 AT AT97905544T patent/ATE219081T1/de active
- 1997-02-21 CA CA002246051A patent/CA2246051A1/en not_active Abandoned
- 1997-02-21 JP JP9530075A patent/JP2000505452A/ja not_active Ceased
- 1997-02-21 BR BR9707616A patent/BR9707616A/pt unknown
- 1997-02-21 WO PCT/SE1997/000294 patent/WO1997030998A1/en not_active Ceased
-
1998
- 1998-08-13 NO NO983711A patent/NO983711L/no not_active Application Discontinuation
- 1998-08-20 IS IS4830A patent/IS4830A/is unknown
-
1999
- 1999-03-26 US US09/276,689 patent/US6054464A/en not_active Expired - Fee Related
-
2000
- 2000-07-30 IL IL13758500A patent/IL137585A0/xx unknown
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