KR920016434A - 4-피리미딘온 유도체, 그의 제법 및 치료에의 이용 - Google Patents
4-피리미딘온 유도체, 그의 제법 및 치료에의 이용 Download PDFInfo
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- KR920016434A KR920016434A KR1019920002504A KR920002504A KR920016434A KR 920016434 A KR920016434 A KR 920016434A KR 1019920002504 A KR1019920002504 A KR 1019920002504A KR 920002504 A KR920002504 A KR 920002504A KR 920016434 A KR920016434 A KR 920016434A
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- alkyl
- optionally substituted
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- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical class O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 title 1
- 238000002560 therapeutic procedure Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 25
- 150000001875 compounds Chemical class 0.000 claims abstract 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 3
- 125000003118 aryl group Chemical group 0.000 claims abstract 3
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract 2
- 125000005110 aryl thio group Chemical group 0.000 claims abstract 2
- 125000004104 aryloxy group Chemical group 0.000 claims abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- -1 1H-tetrazol-5-yl Chemical group 0.000 claims 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- QMHIMXFNBOYPND-UHFFFAOYSA-N 4MTO Natural products CC1=CSC=N1 QMHIMXFNBOYPND-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 150000001409 amidines Chemical class 0.000 claims 1
- 125000005002 aryl methyl group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Ophthalmology & Optometry (AREA)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Liquid Developers In Electrophotography (AREA)
Abstract
Description
Claims (10)
- 일반식(Ⅰ), (Ⅰ')및 (Ⅰ'')을 가지는 3개의 호변체 형태의 화합물 및 유기 또는 무기의 제약적으로 허용되는 그 염.상기 식에서, R1은 적쇄 또는 분지쇄 (C1-7)알킬기 또는 직쇄 또는 분지쇄 (C3-9)알케닐기 또는 시클로 (C3-7)알킬(C1-6)알킬기를 나타내고, R2는 수소원자 또는직쇄 또는 분지쇄 (C1-7)알킬기 또는 시클로 (C3-7) 알킬(C1-3)알킬기 또는 고리상에 임의적으로 치환된 아릴(C1-6)알킬기 또는 고리상에 임의적으로 치환된 아릴옥시(C1-3)알킬기 또는 고리상에 임의적으로 치환된 아릴티오(C1-3)알킬기 또는 고리상에 임의적으로 치환된 아릴술포닐(C1-3)알킬기 또는 고리상에 임의적으로 치환된 헤테로아릴(C1-3)알킬길를 나타내고, R3는CO2H, 1H-테트라졸-5-일, NHCOR11, NHSO2R11, CONHSO2R11또는 CONHOR12기이고, 여기서, R11은 메틸 트리플루오메틸 또는 임의적으로 치횐된 페닐기를 나타내고, R12은 수소원자, 또는 메틸 임의적으로 치환된 페닐기를 나타낸다.
- 제1항에 있어서, R1은 직쇄 또는 분지쇄(C1-7)알킬기를 나타내고, R2는 직쇄 또는 분지쇄 (C1-7)알킬기 또는 시킬로 (C3-7)알킬(C1-3)알킬기, 또는 고리상에 임의적으로 치횐된 아릴(C1-3)알킬기 또는 고리상에 임의적으로 치환된 헤테로고리 (C1-3)알킬기를 나타내고, R3는 CO2H또는 1H-테트라졸-5-일기인 것을 특징으로 하는 화합물.
- 제2항에 있어서, R1은 직쇄 프로필, 부틸 또는 팬틸기를 나타내고, R2는 고리상에 임의적으로 치횐된 아릴메틸, 아릴에틸 도는 헤테로아릴에틸기를 나타내고, R3는 CO2H또는 1H-테트라졸-5-일기인 것을 특징으로 하는 화합물.
- 제3항에 있어서, R1은 직쇄 부틸기를 나타내고, R2는 고리상에 임의적 치환된 벤질 또는 펜에틸 또는피리딜에틸 또는 티에닐에틸 또는 티아졸릴에틸기를 나타내고, R3는 CO2H 또는 1H-테트라졸-5-일기인 것을 특징으로 하는 화합물.
- 제4항에 있어서, R1은 직쇄 부틸기를 나타내고, R2는 페닐메틸기, 4-카르복시페닐메틸기, 페닐에틸기, 4-메톡시페닐에틸기, 4-플루오로페닐에틸기, 3,4,5-트리메톡시페닐에틸기, 3-플루오로-4-메톡시페닐에틸기, 3-피리디닐에틸기, 4-피리디닐에틸기, 5-(4-메틸티아졸)-일-에틸기 또는 3-티에닐에틸기를 나타내고, R3는CO2H또는 1H-테트라졸-5-일기인 것을 특징으로 하는 화합물.
- 제1항에 있어서. 식(Ⅱ)(Ⅱ)의 β-케토에스테르와 식 (Ⅲ)(Ⅲ)의 유도체와 반응시켜 식(Ⅳ)(Ⅳ)의 화합물을 얻고, 이 화합물을 식(Ⅴ)(Ⅴ)의 아미딘과 반응시켜 식(Ⅵ)(Ⅵ)의 화합물을 얻은 다음, R5기를 이 기의 특성에 따라 변환 및/ 또는 탈보호하여 변환후에 식(Ⅰ)의 화합물을 얻는 것을 특징으로 하는 제1항에서 정의한 화합물의 제조방법. 상기 식에서, R1은 제1항에서 정의한 것과 같고, R4는 메틸 또는 에틸기를 나타내고, L은 이탈기를 나타내고, R5는 카르복실기 CO2R6, 여기서 R6은 메틸, 에틸, 1,1-디메틸에틸 또는 벤질기이고, 또는 니트로기, 또는 보호된 1H-테트라졸-5-일기를 나타내고, R2는 제1항에서 정의한 것과 같다.
- 제6항에 있어서, R3가 트리페닐메틸-1H-테트라졸-5-일 또는 1,1-디메틸에틸-1H테트라졸-5-일기인식(Ⅵ)의 화합물을 산성매질에서 탈보호하여 R3이 1H-테트라졸-5-일기이고, R1과R2가 앞에서 정의한 것과 같은 일반식(Ⅰ)의 화합물을 얻은 것을 특징으로 하는 방법,
- 제6항에 있어서 R5가 카르복실산 에스테르이고, R1과 R2가 제1항에서 정의한 것과 같은 식(Ⅵ)의 화합물을 산성 또는 염기성가수분해에 의해 R1과R2가 제1항에서 정의한 것과 같고 R3가 CO2H기인 일반식(Ⅰ)의 화합물로 변환되는 것을 특징으로 하는 방법.
- 제1항 내지 제5항중위 어느 한 항에서 정의한 화합물을 포함하는 것을 특징으로 하는 약제.
- 제1항 내지 제5항중의 어느 한 항에서 정의 한 화합물을 적당한 부형제와 함께 함유하는 덕을 특징으로 하는 제약학적 조성물.※ 참고사항 : 최초출원 내용에 의하여 공개되는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9102032A FR2672892B1 (fr) | 1991-02-20 | 1991-02-20 | Derives de 4-pyrimidinones, leur preparation et leur application en therapeutique. |
FR91-02032 | 1991-02-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
KR920016434A true KR920016434A (ko) | 1992-09-24 |
Family
ID=9409925
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019920002504A KR920016434A (ko) | 1991-02-20 | 1992-02-19 | 4-피리미딘온 유도체, 그의 제법 및 치료에의 이용 |
Country Status (23)
Country | Link |
---|---|
EP (1) | EP0500409B1 (ko) |
JP (1) | JP2529798B2 (ko) |
KR (1) | KR920016434A (ko) |
CN (1) | CN1034171C (ko) |
AT (1) | ATE135695T1 (ko) |
AU (1) | AU650319B2 (ko) |
CA (1) | CA2061456A1 (ko) |
CS (1) | CS49092A3 (ko) |
DE (1) | DE69209113T2 (ko) |
DK (1) | DK0500409T3 (ko) |
ES (1) | ES2086090T3 (ko) |
FI (1) | FI920720A (ko) |
FR (1) | FR2672892B1 (ko) |
GR (1) | GR3019404T3 (ko) |
HU (2) | HUT60477A (ko) |
IE (1) | IE76145B1 (ko) |
IL (1) | IL101014A (ko) |
MX (1) | MX9200690A (ko) |
NO (1) | NO920648L (ko) |
NZ (1) | NZ241659A (ko) |
PL (1) | PL168617B1 (ko) |
RU (1) | RU2073675C1 (ko) |
ZA (1) | ZA921203B (ko) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
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IL102183A (en) * | 1991-06-27 | 1999-11-30 | Takeda Chemical Industries Ltd | The heterocyclic compounds are converted into biphenyl groups, their production and the pharmaceutical compositions containing them |
FR2700543B1 (fr) * | 1993-01-15 | 1995-03-17 | Synthelabo | Sels de dérivés de 4-pyrimidinone, leur préparation et leur application en thérapeutique. |
SE9903028D0 (sv) | 1999-08-27 | 1999-08-27 | Astra Ab | New use |
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 |
MX2009013293A (es) | 2007-06-04 | 2010-02-15 | Synergy Pharmaceuticals Inc | Agonistas de guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos. |
AU2009256157B2 (en) | 2008-06-04 | 2014-12-18 | Bausch Health Ireland Limited | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
EP2321341B1 (en) | 2008-07-16 | 2017-02-22 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
UY32409A (es) * | 2009-01-30 | 2010-08-31 | Takeda Pharmaceutical | Compuesto de anillo fusionado y su uso |
US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
EP2970384A1 (en) | 2013-03-15 | 2016-01-20 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
AU2014235209B2 (en) | 2013-03-15 | 2018-06-14 | Bausch Health Ireland Limited | Guanylate cyclase receptor agonists combined with other drugs |
EP4424697A3 (en) | 2013-06-05 | 2024-12-25 | Bausch Health Ireland Limited | Ultra-pure agonists of guanylate cyclase c, method of making and using same |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1334092C (en) * | 1986-07-11 | 1995-01-24 | David John Carini | Angiotensin ii receptor blocking imidazoles |
US5064825A (en) * | 1989-06-01 | 1991-11-12 | Merck & Co., Inc. | Angiotensin ii antagonists |
KR0163595B1 (ko) * | 1989-06-30 | 1998-12-01 | 미리암디, 메코너헤이 | 치환된 이미다졸 |
EP0407342A3 (en) * | 1989-07-06 | 1991-07-10 | Ciba-Geigy Ag | Pyrimidine derivatives |
EP0424317A3 (en) * | 1989-10-19 | 1991-09-25 | Ciba-Geigy Ag | Pyrimidines |
EP0435827A3 (en) * | 1989-12-28 | 1991-11-13 | Ciba-Geigy Ag | Diaza compounds |
JPH05505609A (ja) * | 1990-03-30 | 1993-08-19 | メルク・エンド・カムパニー・インコーポレーテツド | 置換ピリミジン、ピリミジノンおよびピリドリミジン |
IE912114A1 (en) * | 1990-07-02 | 1992-01-15 | Union Pharma Scient Appl | Novel pyrimidine derivatives which are angiotensin ii¹receptor antagonists, their methods of preparation and¹pharmaceutical compositions in which they are present |
-
1991
- 1991-02-20 FR FR9102032A patent/FR2672892B1/fr not_active Expired - Fee Related
-
1992
- 1992-02-03 ES ES92400269T patent/ES2086090T3/es not_active Expired - Lifetime
- 1992-02-03 EP EP92400269A patent/EP0500409B1/fr not_active Expired - Lifetime
- 1992-02-03 DK DK92400269.4T patent/DK0500409T3/da active
- 1992-02-03 AT AT92400269T patent/ATE135695T1/de not_active IP Right Cessation
- 1992-02-03 DE DE69209113T patent/DE69209113T2/de not_active Expired - Fee Related
- 1992-02-19 HU HU9200532A patent/HUT60477A/hu unknown
- 1992-02-19 FI FI920720A patent/FI920720A/fi unknown
- 1992-02-19 ZA ZA921203A patent/ZA921203B/xx unknown
- 1992-02-19 MX MX9200690A patent/MX9200690A/es not_active IP Right Cessation
- 1992-02-19 NZ NZ241659A patent/NZ241659A/xx unknown
- 1992-02-19 IE IE920525A patent/IE76145B1/en not_active IP Right Cessation
- 1992-02-19 RU SU925010817A patent/RU2073675C1/ru active
- 1992-02-19 NO NO92920648A patent/NO920648L/no unknown
- 1992-02-19 CS CS92490A patent/CS49092A3/cs unknown
- 1992-02-19 IL IL10101492A patent/IL101014A/en not_active IP Right Cessation
- 1992-02-19 PL PL92293531A patent/PL168617B1/pl unknown
- 1992-02-19 KR KR1019920002504A patent/KR920016434A/ko not_active Application Discontinuation
- 1992-02-19 JP JP4031862A patent/JP2529798B2/ja not_active Expired - Lifetime
- 1992-02-19 CN CN92101114A patent/CN1034171C/zh not_active Expired - Fee Related
- 1992-02-19 AU AU11059/92A patent/AU650319B2/en not_active Ceased
- 1992-02-19 CA CA002061456A patent/CA2061456A1/en not_active Abandoned
-
1995
- 1995-06-29 HU HU95P/P00554P patent/HU211886A9/hu unknown
-
1996
- 1996-03-21 GR GR960400758T patent/GR3019404T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
IL101014A0 (en) | 1992-11-15 |
IL101014A (en) | 1996-06-18 |
JP2529798B2 (ja) | 1996-09-04 |
FI920720A (fi) | 1992-08-21 |
FI920720A0 (fi) | 1992-02-19 |
FR2672892A1 (fr) | 1992-08-21 |
HUT60477A (en) | 1992-09-28 |
CS49092A3 (en) | 1992-09-16 |
ZA921203B (en) | 1992-11-25 |
PL293531A1 (en) | 1992-08-24 |
AU650319B2 (en) | 1994-06-16 |
GR3019404T3 (en) | 1996-06-30 |
ATE135695T1 (de) | 1996-04-15 |
JPH04346980A (ja) | 1992-12-02 |
HU9200532D0 (en) | 1992-05-28 |
IE76145B1 (en) | 1997-10-08 |
CN1034171C (zh) | 1997-03-05 |
HU211886A9 (en) | 1995-12-28 |
CA2061456A1 (en) | 1992-08-21 |
CN1064269A (zh) | 1992-09-09 |
EP0500409B1 (fr) | 1996-03-20 |
FR2672892B1 (fr) | 1994-01-14 |
NZ241659A (en) | 1993-03-26 |
MX9200690A (es) | 1992-08-01 |
DE69209113D1 (de) | 1996-04-25 |
PL168617B1 (pl) | 1996-03-29 |
NO920648L (no) | 1992-08-21 |
DK0500409T3 (da) | 1996-07-15 |
EP0500409A1 (fr) | 1992-08-26 |
IE920525A1 (en) | 1992-08-26 |
NO920648D0 (no) | 1992-02-19 |
DE69209113T2 (de) | 1996-10-31 |
AU1105992A (en) | 1992-08-27 |
RU2073675C1 (ru) | 1997-02-20 |
ES2086090T3 (es) | 1996-06-16 |
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