KR960701885A - 피리도[1,2,3-데]퀴녹살린 유도체, 그의 제조 방법 및 그의 약제로서의 용도(Pyrido[1,2,3-de]quinoxaline Derivatives, Process for Preparing the Same and their Use in Medicaments) - Google Patents
피리도[1,2,3-데]퀴녹살린 유도체, 그의 제조 방법 및 그의 약제로서의 용도(Pyrido[1,2,3-de]quinoxaline Derivatives, Process for Preparing the Same and their Use in Medicaments)Info
- Publication number
- KR960701885A KR960701885A KR1019950704707A KR19950704707A KR960701885A KR 960701885 A KR960701885 A KR 960701885A KR 1019950704707 A KR1019950704707 A KR 1019950704707A KR 19950704707 A KR19950704707 A KR 19950704707A KR 960701885 A KR960701885 A KR 960701885A
- Authority
- KR
- South Korea
- Prior art keywords
- quinoxaline
- pyrido
- dioxo
- trifluoromethyl
- phosphonic acid
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract 3
- 239000003814 drug Substances 0.000 title claims 2
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 title abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 9
- 239000001257 hydrogen Substances 0.000 claims abstract 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract 7
- 150000002367 halogens Chemical class 0.000 claims abstract 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 4
- -1 -POXY Inorganic materials 0.000 claims abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- GWMJWKVKNKBJIF-UHFFFAOYSA-N quinoxalin-5-ylphosphonic acid Chemical compound C1=CN=C2C(P(O)(=O)O)=CC=CC2=N1 GWMJWKVKNKBJIF-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- AGPLVGVSJGZCRZ-UHFFFAOYSA-N (7-chloro-2,3-dioxo-1,4-diazatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-12-yl)phosphonic acid Chemical compound N1C(=O)C(=O)N2C(P(O)(=O)O)CCC3=CC(Cl)=CC1=C32 AGPLVGVSJGZCRZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- YVJWXADGPXYRIH-UHFFFAOYSA-N 5-diethoxyphosphorylquinoxaline Chemical compound C1=CN=C2C(P(=O)(OCC)OCC)=CC=CC2=N1 YVJWXADGPXYRIH-UHFFFAOYSA-N 0.000 claims 1
- SVLOSGHRGNIFLW-UHFFFAOYSA-N 8-iodo-9-trifluoromethyl-2,3-dioxo-1,2,3,5,6,7-hexahydro-pyrido[1,2,3-de]quinoxaline-5-phosphonic acid Chemical compound N1C(=O)C(=O)N2C(P(O)(=O)O)CCC3=C(I)C(C(F)(F)F)=CC1=C32 SVLOSGHRGNIFLW-UHFFFAOYSA-N 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- YKFPGLPNMJFDCQ-UHFFFAOYSA-N [2,3-dioxo-7-(trifluoromethyl)-1,4-diazatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-10-yl]phosphonic acid Chemical compound C1=C(C(F)(F)F)C=C2NC(=O)C(=O)N3CCC(P(O)(=O)O)C1=C23 YKFPGLPNMJFDCQ-UHFFFAOYSA-N 0.000 claims 1
- FJECEPCBYAPWML-UHFFFAOYSA-N [2,3-dioxo-7-(trifluoromethyl)-1,4-diazatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-11-yl]phosphonic acid Chemical compound N1C(=O)C(=O)N2CC(P(O)(=O)O)CC3=CC(C(F)(F)F)=CC1=C32 FJECEPCBYAPWML-UHFFFAOYSA-N 0.000 claims 1
- UATDVWDTIGFTLE-UHFFFAOYSA-N [8-amino-2,3-dioxo-7-(trifluoromethyl)-1,4-diazatricyclo[7.3.1.05,13]trideca-5(13),6,8-trien-12-yl]phosphonic acid Chemical compound N1C(=O)C(=O)N2C3=C1C=C(C(F)(F)F)C(N)=C3CCC2P(O)(O)=O UATDVWDTIGFTLE-UHFFFAOYSA-N 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 230000002862 amidating effect Effects 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000006575 electron-withdrawing group Chemical group 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 239000006260 foam Substances 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 230000000802 nitrating effect Effects 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- 150000002912 oxalic acid derivatives Chemical class 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 239000008177 pharmaceutical agent Substances 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- 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
- A61P25/28—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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biochemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
본 발명은 하기 일반식(I)의 피리도[1,2,3-데]퀴녹살린 유도체, 그의 제조 및 약제 제제로서의 용도에 관한 것이다.
상기 식 중, R1, R2및 R3은 각각 수소, -POXY, 할로겐 또는 -COR을 의미하고, R4는 수소 또는 OH를 의미하며, R5, R6및 R7은 동일하거나 또는 상이하며, 수소, 할로겐, 니트로, NR12R13, 시아노, CF3, C1-6알킬 또는 C1-4알콕시를 의미하거나, 또는 R5및 R6또는 R6및 R7은 융합 벤젠 고리를 나타내고,
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (4)
- 하기 일반식(I)의 화합물 및 그의 이성질체 또는 염.상기 식 중, R1, R2및 R3은 각각 수소, -POXY, 할로겐 또는 -COR을 의미하고, R4는 수소 또는 OH를 의미하며, R5, R6및 R7은 동일하거나 또는 상이하며, 수소, 할로겐, 니트로, NR12R13, 시아노, CF3, C1-6알킬 또는 C1-4알콕시를 의미하거나, 또는 R5및 R6또는 R6및 R7은 융합 벤젠 고리를 나타내고, 는 단일 또는 이중 결합을 의미하며, X 및 Y는 동일하거나 또는 상이하며, 히드록시, C1-6알콕시, -O-(CH2)n-O-, C1-4알킬 또는 NR9R10을 의미하고, n은 1,2 또는 3이며, R은 히드록시, C1-6알콕시 또는 NR9R10을 의미하고, R9및 R10과 R12및 R13은 동일하거나 또는 상이하고, 수소,-CO-C1-6알킬, 페닐 또는 C1-6알킬(이들 기는 C1-4알킬로 임의로 일- 또는 이치환되거나 아미노기 또는 C1-4알콕시로 임의로 치환될 수 있음)을 의미하거나 또는 질소 원자와 함께 포화 5 내지 7원 헤테로사이클(이 헤테로사이클은 또 다른 산소, 황 또는 질소 원자를 함유할 수 있고 임의로 치환될 수 있음)을 형성하거나 또는 불포화 5원 헤테로사이클(이 헤테로사이클은 1 내지 3개의 N 원자를 함유할 수 있고 치환될 수 있음)을 형성할 수 있다.
- 8-(1-이미다졸릴)-9-트리플루오로메틸-2,3-디옥소-1,2,3,5,6,7-헥사히드로-피리도[1,2,3-데]퀴녹살린-5-포스폰산, 8-요오도-9-트리플루오로메틸-2,3-디옥소-1,2,3,5,6,7-헥사히드로-피리도[1,2,3-데]퀴녹살린-5-포스폰산, 8-(1-피롤릴)-9-트리플루오로메틸-2,3-디옥소-1,2,3,5,6,7-헥사히드로-피리도[1,2,3-데]퀴녹살린-5-포스폰산, 8-모르폴리노-9-트리플루오로메틸-2,3-디옥소-1,2,3,5,6,7-헥사이드로-피리도[1,2,3-데]퀴녹살린-5-포스폰산, 8-아미노-9-트리플루오로메틸-2,3-디옥소-1,2,3,5,6,7-헥사히드로-피리도[1,2,3-데]퀴녹살린-5-포스폰산, 9-트리플루오로메 틸-2,3-디옥소-1,2,3,5,6,7-헥사히드로-피리도[1,2,3-데]퀴녹살린-6-포스폰산, 9-클로로-2,3-디옥소-1,2,3,5,6,7-헥사히드로-피리도[1,2,3-데]퀴녹살린-5-포스폰산, 9-트리플루오로메틸-2,3-디옥소-1,2,3,5,6,7-헥사이드로-피리도[1,2,3-데]퀴녹살린 -5-포스폰산, 9-트리플루오로메틸-2,3-디 옥소-1,2,3,5,6,7-헥사히드로-피리도[1,2,3-데]퀴녹살린-7-포스폰산, 또는 9-트리플루오로메틸-2,3-디옥소-1,2,3,5,6,7-헥사이드로-피리도[1,2,3-데]퀴녹살린-5-포스폰산 디에틸 에스테르.
- 제1항 또는 제2항에 따른 화합물을 기재로 함유하는 약제.
- a)하기 일반식(Ⅱ)의 화합물을 옥살산 또는 반응성 옥살산 유도체와 반응시키고, NO2기의 도입 및 환원후 임의로 환화시키며, R1, R2및(또는) R3이 할로겐을 의미하는 경우 임의로 XYP-O-C1-4알킬과 반응시키거나 또는 카르보닐화시키거나, 또는 b)하기 일반식(Ⅲ)의 화합물을 할로겐화 또는 니트로화시키고, 이어서 임의로, 에스테르기를 비누화시키거나 또는 산기를 에스테르화 또는 아미드화시키거나 또는 니트로기를 아미노기로 환원시키거나 또는 아미노기를 알킬화 또는 아실화시키거나 또는 아미노기를 할로겐 또는 시아노로 치환되거나 또는 니트로기 또는 할로겐을 도입 또는 친핵 치환하거나 또는 이성질체를 분리하거나 또는 염을 형성시키는 것을 특징으로 하는 일반식(I)의 화합물의 제조 방법.(식 중, R11은 H, NO2또는 -NH-R4이고, R1내지 R7은 상술한 의미를 가지고, R5', R6'또는 R7'는 수소또는 전자흡인기를 의미함)※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4314593.0 | 1993-04-28 | ||
| DE4314593A DE4314593A1 (de) | 1993-04-28 | 1993-04-28 | Pyrido(1,2,3-de)chinoxalinderivate, Verfahren zu deren Herstellung und ihre Verwendung von Arzneimitteln |
| PCT/DE1994/000494 WO1994025472A1 (de) | 1993-04-28 | 1994-04-28 | Pyrido[1,2,3-de]chinoxalinderivate, verfahren zu deren herstellung und ihre verwendung in arzneimitteln |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR960701885A true KR960701885A (ko) | 1996-03-28 |
Family
ID=6487060
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019950704707A KR960701885A (ko) | 1993-04-28 | 1994-04-28 | 피리도[1,2,3-데]퀴녹살린 유도체, 그의 제조 방법 및 그의 약제로서의 용도(Pyrido[1,2,3-de]quinoxaline Derivatives, Process for Preparing the Same and their Use in Medicaments) |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5750526A (ko) |
| EP (1) | EP0696291B1 (ko) |
| JP (1) | JPH09500359A (ko) |
| KR (1) | KR960701885A (ko) |
| CN (1) | CN1043576C (ko) |
| AT (1) | ATE169925T1 (ko) |
| AU (1) | AU686160B2 (ko) |
| CA (1) | CA2161427A1 (ko) |
| CZ (1) | CZ277795A3 (ko) |
| DE (2) | DE4314593A1 (ko) |
| DK (1) | DK0696291T3 (ko) |
| ES (1) | ES2122274T3 (ko) |
| FI (1) | FI955141A0 (ko) |
| HU (1) | HUT74173A (ko) |
| IL (1) | IL109396A (ko) |
| NO (1) | NO305439B1 (ko) |
| NZ (1) | NZ265600A (ko) |
| PL (1) | PL174418B1 (ko) |
| RU (1) | RU2140924C1 (ko) |
| SK (1) | SK131995A3 (ko) |
| WO (1) | WO1994025472A1 (ko) |
| ZA (1) | ZA942970B (ko) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997038691A1 (fr) * | 1996-04-17 | 1997-10-23 | Sumitomo Pharmaceuticals Co., Ltd. | Medicament pour neuropathie retinienne |
| US6063774A (en) * | 1996-12-16 | 2000-05-16 | Warner-Lambert Company | Tricyclic quinoxaline derivatives as neuroprotective agents |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69016430T2 (de) * | 1989-06-09 | 1995-06-01 | Upjohn Co | Heterozyklische amine mit zns-wirksamkeit. |
| US5273975A (en) * | 1989-06-09 | 1993-12-28 | The Upjohn Company | Heterocyclic amines having central nervous system activity |
| JPH05117276A (ja) * | 1991-10-23 | 1993-05-14 | Sumitomo Pharmaceut Co Ltd | 新規な３環性キノキサリンジオン誘導体 |
-
1993
- 1993-04-28 DE DE4314593A patent/DE4314593A1/de not_active Withdrawn
-
1994
- 1994-04-22 IL IL109396A patent/IL109396A/xx not_active IP Right Cessation
- 1994-04-28 DE DE59406739T patent/DE59406739D1/de not_active Expired - Lifetime
- 1994-04-28 CZ CZ952777A patent/CZ277795A3/cs unknown
- 1994-04-28 AU AU66756/94A patent/AU686160B2/en not_active Ceased
- 1994-04-28 SK SK1319-95A patent/SK131995A3/sk unknown
- 1994-04-28 PL PL94311295A patent/PL174418B1/pl unknown
- 1994-04-28 DK DK94914314T patent/DK0696291T3/da active
- 1994-04-28 RU RU95119828A patent/RU2140924C1/ru active
- 1994-04-28 CN CN94191912A patent/CN1043576C/zh not_active Expired - Fee Related
- 1994-04-28 JP JP6523752A patent/JPH09500359A/ja active Pending
- 1994-04-28 HU HU9502810A patent/HUT74173A/hu unknown
- 1994-04-28 CA CA002161427A patent/CA2161427A1/en not_active Abandoned
- 1994-04-28 US US08/535,250 patent/US5750526A/en not_active Expired - Fee Related
- 1994-04-28 ZA ZA942970A patent/ZA942970B/xx unknown
- 1994-04-28 EP EP94914314A patent/EP0696291B1/de not_active Expired - Lifetime
- 1994-04-28 NZ NZ265600A patent/NZ265600A/en unknown
- 1994-04-28 ES ES94914314T patent/ES2122274T3/es not_active Expired - Lifetime
- 1994-04-28 WO PCT/DE1994/000494 patent/WO1994025472A1/de not_active Application Discontinuation
- 1994-04-28 KR KR1019950704707A patent/KR960701885A/ko not_active Application Discontinuation
- 1994-04-28 AT AT94914314T patent/ATE169925T1/de not_active IP Right Cessation
-
1995
- 1995-10-27 FI FI955141A patent/FI955141A0/fi unknown
- 1995-10-27 NO NO954317A patent/NO305439B1/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE4314593A1 (de) | 1994-11-03 |
| EP0696291B1 (de) | 1998-08-19 |
| PL174418B1 (pl) | 1998-07-31 |
| RU2140924C1 (ru) | 1999-11-10 |
| ES2122274T3 (es) | 1998-12-16 |
| NZ265600A (en) | 1996-09-25 |
| AU6675694A (en) | 1994-11-21 |
| NO305439B1 (no) | 1999-05-31 |
| HU9502810D0 (en) | 1995-11-28 |
| FI955141A (fi) | 1995-10-27 |
| SK131995A3 (en) | 1996-07-03 |
| AU686160B2 (en) | 1998-02-05 |
| DE59406739D1 (de) | 1998-09-24 |
| DK0696291T3 (da) | 1999-05-25 |
| CN1121720A (zh) | 1996-05-01 |
| ATE169925T1 (de) | 1998-09-15 |
| CZ277795A3 (en) | 1996-02-14 |
| WO1994025472A1 (de) | 1994-11-10 |
| JPH09500359A (ja) | 1997-01-14 |
| NO954317D0 (no) | 1995-10-27 |
| ZA942970B (en) | 1995-01-19 |
| HUT74173A (en) | 1996-11-28 |
| FI955141A0 (fi) | 1995-10-27 |
| CN1043576C (zh) | 1999-06-09 |
| EP0696291A1 (de) | 1996-02-14 |
| IL109396A (en) | 1997-11-20 |
| CA2161427A1 (en) | 1994-11-10 |
| PL311295A1 (en) | 1996-02-05 |
| NO954317L (no) | 1995-12-28 |
| IL109396A0 (en) | 1994-07-31 |
| US5750526A (en) | 1998-05-12 |
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Legal Events
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|---|---|---|---|
| A201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| E601 | Decision to refuse application |