NZ323387A - Quinoline derivatives having neurokinin antagonist activity, preparation and use thereof - Google Patents
Quinoline derivatives having neurokinin antagonist activity, preparation and use thereofInfo
- Publication number
- NZ323387A NZ323387A NZ323387A NZ32338796A NZ323387A NZ 323387 A NZ323387 A NZ 323387A NZ 323387 A NZ323387 A NZ 323387A NZ 32338796 A NZ32338796 A NZ 32338796A NZ 323387 A NZ323387 A NZ 323387A
- Authority
- NZ
- New Zealand
- Prior art keywords
- compound
- formula
- group
- mmol
- alkyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 230000000694 effects Effects 0.000 title description 10
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 2
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- 239000002462 tachykinin receptor antagonist Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 214
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 26
- 239000012453 solvate Substances 0.000 claims abstract description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
- 238000011282 treatment Methods 0.000 claims abstract description 16
- 230000008569 process Effects 0.000 claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 6
- 239000003814 drug Substances 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 4
- 235000011468 Albizia julibrissin Nutrition 0.000 claims description 50
- 241001070944 Mimosa Species 0.000 claims description 50
- -1 2-pyrazinylcarbonyl Chemical group 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 15
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- 125000003118 aryl group Chemical group 0.000 claims description 13
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- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
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- NHXYSAFTNPANFK-HDMCBQFHSA-N Neurokinin B Chemical compound C([C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)C(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCSC)NC(=O)[C@@H](N)CC(O)=O)C1=CC=CC=C1 NHXYSAFTNPANFK-HDMCBQFHSA-N 0.000 description 5
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- 150000007529 inorganic bases Chemical class 0.000 description 1
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 235000010445 lecithin Nutrition 0.000 description 1
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- GNBWUEAMCSHHMO-UHFFFAOYSA-N methyl 2-carbonochloridoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(Cl)=O GNBWUEAMCSHHMO-UHFFFAOYSA-N 0.000 description 1
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- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- YYTWEEOFRNSTKS-UHFFFAOYSA-N n,n'-dicyclohexylmethanediimine;1-hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1.C1CCCCC1N=C=NC1CCCCC1 YYTWEEOFRNSTKS-UHFFFAOYSA-N 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
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- 125000003431 oxalo group Chemical group 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical class C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
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- 238000011197 physicochemical method Methods 0.000 description 1
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- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- LEWDKQKVAFOMPI-UHFFFAOYSA-N quinoline-4-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CC=NC2=C1 LEWDKQKVAFOMPI-UHFFFAOYSA-N 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
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- 125000006413 ring segment Chemical group 0.000 description 1
- 102220079670 rs759826252 Human genes 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
- C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Pulmonology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NZ500371A NZ500371A (en) | 1995-11-24 | 1996-11-22 | NK-2/NK-3 antagonists and their use in treating respiratory disease |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI952461 IT1276170B1 (it) | 1995-11-24 | 1995-11-24 | Derivati chinolinici |
| IT96MI001689 IT1307331B1 (it) | 1996-08-02 | 1996-08-02 | Derivati chinolinici |
| PCT/EP1996/005203 WO1997021680A1 (en) | 1995-11-24 | 1996-11-22 | Quinoline derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ323387A true NZ323387A (en) | 2000-02-28 |
Family
ID=26331326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ323387A NZ323387A (en) | 1995-11-24 | 1996-11-22 | Quinoline derivatives having neurokinin antagonist activity, preparation and use thereof |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US6277862B1 (enExample) |
| EP (1) | EP0876347B1 (enExample) |
| JP (1) | JP2000501104A (enExample) |
| KR (1) | KR19990071597A (enExample) |
| CN (1) | CN1207730A (enExample) |
| AP (1) | AP9801237A0 (enExample) |
| AR (1) | AR004972A1 (enExample) |
| AT (1) | ATE289994T1 (enExample) |
| BG (1) | BG102558A (enExample) |
| BR (1) | BR9611820A (enExample) |
| CA (1) | CA2238298A1 (enExample) |
| CZ (1) | CZ157998A3 (enExample) |
| DE (1) | DE69634416T2 (enExample) |
| EA (1) | EA002124B1 (enExample) |
| ES (1) | ES2236757T3 (enExample) |
| IL (1) | IL124522A0 (enExample) |
| MX (1) | MX9804107A (enExample) |
| NO (1) | NO311212B1 (enExample) |
| NZ (1) | NZ323387A (enExample) |
| OA (1) | OA11010A (enExample) |
| PL (1) | PL326967A1 (enExample) |
| SK (1) | SK66798A3 (enExample) |
| TR (1) | TR199800924T2 (enExample) |
| TW (1) | TW353066B (enExample) |
| UY (1) | UY24733A1 (enExample) |
| WO (1) | WO1997021680A1 (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU219131B (hu) * | 1991-10-18 | 2001-02-28 | Monsanto Co. | Módszer és fungicid készítmény növények torsgombabetegségének gátlására és a hatóanyagok |
| SE9703407D0 (sv) * | 1997-09-19 | 1997-09-19 | Astra Ab | New use |
| SE9802073D0 (sv) | 1998-06-11 | 1998-06-11 | Astra Ab | New use |
| GB9825554D0 (en) * | 1998-11-20 | 1999-01-13 | Smithkline Beecham Spa | Novel Compounds |
| US7037922B1 (en) | 2000-03-10 | 2006-05-02 | Neurogen Corporation | Aryl fused 2,4-disubstituted pyridines: NK3 receptor ligands |
| ATE247652T1 (de) | 1999-03-29 | 2003-09-15 | Neurogen Corp | 4-substituierte chinolinderivate als nk-3 und/oder gaba(a) rezeptor liganden |
| WO2000064877A1 (en) * | 1999-04-26 | 2000-11-02 | Neurogen Corporation | 2-aminoquinolinecarboxamides: neurokinin receptor ligands |
| EP1385839B1 (en) * | 2001-04-11 | 2006-02-22 | GlaxoSmithKline S.p.A. | 3-substituted quinoline-4-carboxamide derivatives as nk-3 and nk-2 receptor antagonists |
| WO2002089802A2 (en) * | 2001-05-08 | 2002-11-14 | Schering Corporation | Use of neurokinin receptor antagonists to treat androgen-dependent diseases |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| BR122018074353B8 (pt) | 2003-01-28 | 2023-05-02 | Ironwood Pharmaceuticals Inc | composição farmacêutica, polipeptídeo e métodos para a produção dos mesmos |
| GB0303086D0 (en) * | 2003-02-11 | 2003-03-19 | Merck Sharp & Dohme | New compounds |
| GB0419192D0 (en) | 2004-08-27 | 2004-09-29 | Merck Sharp & Dohme | Therapeutic agents |
| WO2006052722A1 (en) * | 2004-11-09 | 2006-05-18 | Smithkline Beecham Corporation | Glycogen phosphorylase inhibitor compounds and pharmaceutical compositions thereof |
| GB0425077D0 (en) * | 2004-11-12 | 2004-12-15 | Smithkline Beecham Corp | Novel compounds |
| GB0515580D0 (en) | 2005-07-29 | 2005-09-07 | Merck Sharp & Dohme | Therapeutic compounds |
| CN101282961A (zh) * | 2005-08-11 | 2008-10-08 | 阿斯利康(瑞典)有限公司 | 作为nk3受体调节剂的烷基吡啶基喹啉 |
| AR057130A1 (es) | 2005-09-21 | 2007-11-14 | Astrazeneca Ab | Quinolinas de alquilsulfoxido y una composicion farmaceutica |
| TW201018662A (en) * | 2005-12-12 | 2010-05-16 | Astrazeneca Ab | Alkylsulphonamide quinolines |
| WO2008151257A2 (en) | 2007-06-04 | 2008-12-11 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| US20100305207A1 (en) * | 2007-09-28 | 2010-12-02 | Pierette Banker | Glycogen phosphorylase inhibitor compound and pharmaceutical composition thereof |
| CN101861303A (zh) * | 2007-09-28 | 2010-10-13 | 葛兰素史密丝克莱恩有限责任公司 | 糖原磷酸化酶抑制剂化合物和其药物组合物 |
| ES2627848T3 (es) | 2008-06-04 | 2017-07-31 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos |
| ES2624828T3 (es) | 2008-07-16 | 2017-07-17 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros |
| CN103819403B (zh) | 2008-12-31 | 2017-01-04 | 阿德利克斯公司 | 用于治疗与体液潴留或盐超负荷有关的病症和胃肠道病症的化合物和方法 |
| WO2018129556A1 (en) | 2017-01-09 | 2018-07-12 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| US10376481B2 (en) | 2012-08-21 | 2019-08-13 | Ardelyx, Inc. | Compounds and methods for inhibiting NHE-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| RU2015107019A (ru) | 2012-08-21 | 2016-10-10 | Эрделикс Инк. | Соединения и способы для ингибирования nhe-опосредованного антипорта в лечении расстройств, ассоциированных с задержкой жидкости или солевой перегрузкой и заболеваний желудочно-кишечного тракта |
| EP2968439A2 (en) | 2013-03-15 | 2016-01-20 | Synergy Pharmaceuticals Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| US9708367B2 (en) | 2013-03-15 | 2017-07-18 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase and their uses |
| CN105392483B (zh) | 2013-04-12 | 2019-03-15 | 阿德利克斯公司 | 用于抑制磷酸盐转运的nhe3结合化合物和方法 |
| BR112015026519A2 (pt) | 2013-04-19 | 2017-07-25 | Astrazeneca Ab | composto antagonista do receptor nk3 (nk3ra) para uso em um método destinado ao tratamento de síndrome do ovário policístico (sop) |
| PL3004138T3 (pl) | 2013-06-05 | 2024-07-29 | Bausch Health Ireland Limited | Ultra-oczyszczeni agoniści peptydowi cyklazy guanylanowej C, sposób ich uzyskiwania i ich zastosowanie |
| WO2017072629A1 (en) | 2015-10-29 | 2017-05-04 | Cadila Healthcare Limited | Pharmaceutical combination of nk3 receptor antagonist and biguanides |
| EA201991676A1 (ru) | 2017-01-09 | 2020-01-30 | Арделикс, Инк. | Ингибиторы nhe-опосредованного антипорта |
| KR20240090875A (ko) | 2017-01-09 | 2024-06-21 | 알데릭스, 인코포레이티드 | 위장관 장애를 치료하는 데 유용한 화합물 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2538388B1 (fr) * | 1982-12-24 | 1985-06-21 | Pharmuka Lab | Nouveaux derives de naphtalene- ou azanaphtalenecarboxamide, leurs procedes de preparation et leur utilisation comme medicaments |
| JPS63119455A (ja) * | 1986-06-27 | 1988-05-24 | Nippon Shinyaku Co Ltd | グリシン誘導体 |
| DE69531458T2 (de) * | 1994-05-27 | 2004-08-05 | Glaxosmithkline S.P.A. | Chinolinderivate als tachykinin nk3 rezeptor antagonisten |
| IT1270615B (it) * | 1994-07-14 | 1997-05-07 | Smithkline Beecham Farma | Uso di derivati di chinolina |
-
1996
- 1996-11-22 AT AT96941023T patent/ATE289994T1/de not_active IP Right Cessation
- 1996-11-22 US US09/077,151 patent/US6277862B1/en not_active Expired - Fee Related
- 1996-11-22 WO PCT/EP1996/005203 patent/WO1997021680A1/en not_active Ceased
- 1996-11-22 BR BR9611820A patent/BR9611820A/pt not_active Application Discontinuation
- 1996-11-22 NZ NZ323387A patent/NZ323387A/en unknown
- 1996-11-22 CA CA002238298A patent/CA2238298A1/en not_active Abandoned
- 1996-11-22 IL IL12452296A patent/IL124522A0/xx unknown
- 1996-11-22 EA EA199800477A patent/EA002124B1/ru not_active IP Right Cessation
- 1996-11-22 ES ES96941023T patent/ES2236757T3/es not_active Expired - Lifetime
- 1996-11-22 DE DE69634416T patent/DE69634416T2/de not_active Expired - Fee Related
- 1996-11-22 JP JP9521658A patent/JP2000501104A/ja active Pending
- 1996-11-22 EP EP96941023A patent/EP0876347B1/en not_active Expired - Lifetime
- 1996-11-22 AP APAP/P/1998/001237A patent/AP9801237A0/en unknown
- 1996-11-22 CN CN96199753A patent/CN1207730A/zh active Pending
- 1996-11-22 KR KR1019980703873A patent/KR19990071597A/ko not_active Withdrawn
- 1996-11-22 SK SK667-98A patent/SK66798A3/sk unknown
- 1996-11-22 PL PL96326967A patent/PL326967A1/xx unknown
- 1996-11-22 TR TR1998/00924T patent/TR199800924T2/xx unknown
- 1996-11-22 CZ CZ981579A patent/CZ157998A3/cs unknown
- 1996-11-23 TW TW085114500A patent/TW353066B/zh active
- 1996-11-25 AR ARP960105317A patent/AR004972A1/es not_active Application Discontinuation
-
1997
- 1997-09-30 UY UY24733A patent/UY24733A1/es not_active Application Discontinuation
-
1998
- 1998-05-22 NO NO19982331A patent/NO311212B1/no unknown
- 1998-05-22 MX MX9804107A patent/MX9804107A/es unknown
- 1998-05-22 OA OA9800061A patent/OA11010A/en unknown
- 1998-06-18 BG BG102558A patent/BG102558A/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AP9801237A0 (en) | 1998-06-30 |
| DE69634416T2 (de) | 2005-12-29 |
| JP2000501104A (ja) | 2000-02-02 |
| NO311212B1 (no) | 2001-10-29 |
| NO982331D0 (no) | 1998-05-22 |
| PL326967A1 (en) | 1998-11-09 |
| OA11010A (en) | 2003-03-06 |
| DE69634416D1 (de) | 2005-04-07 |
| WO1997021680A1 (en) | 1997-06-19 |
| TR199800924T2 (xx) | 1998-08-21 |
| TW353066B (en) | 1999-02-21 |
| EA199800477A1 (ru) | 1998-12-24 |
| UY24733A1 (es) | 2001-08-27 |
| IL124522A0 (en) | 1998-12-06 |
| ES2236757T3 (es) | 2005-07-16 |
| AR004972A1 (es) | 1999-04-07 |
| BG102558A (bg) | 1999-03-31 |
| CN1207730A (zh) | 1999-02-10 |
| BR9611820A (pt) | 1999-07-13 |
| SK66798A3 (en) | 1999-01-11 |
| KR19990071597A (ko) | 1999-09-27 |
| ATE289994T1 (de) | 2005-03-15 |
| NO982331L (no) | 1998-07-22 |
| MX9804107A (es) | 1998-09-30 |
| EP0876347B1 (en) | 2005-03-02 |
| CZ157998A3 (cs) | 1998-12-16 |
| EP0876347A1 (en) | 1998-11-11 |
| US6277862B1 (en) | 2001-08-21 |
| CA2238298A1 (en) | 1997-06-19 |
| EA002124B1 (ru) | 2001-12-24 |
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