KR930002316A - N-알킬화 1,4-디하이드로피리 딘디카르복실산 에스테르 - Google Patents
N-알킬화 1,4-디하이드로피리 딘디카르복실산 에스테르 Download PDFInfo
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- KR930002316A KR930002316A KR1019920013669A KR920013669A KR930002316A KR 930002316 A KR930002316 A KR 930002316A KR 1019920013669 A KR1019920013669 A KR 1019920013669A KR 920013669 A KR920013669 A KR 920013669A KR 930002316 A KR930002316 A KR 930002316A
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- South Korea
- Prior art keywords
- isopropyl
- dihydropyridine
- dicarboxylate
- methoxyethyl
- trimethyl
- Prior art date
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- -1 N-alkylated 1,4-dihydropyridine dicarboxylic acid ester Chemical class 0.000 title claims 13
- 150000001875 compounds Chemical class 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- SYHPGXUWPYJXOO-UHFFFAOYSA-N 1,4-dihydropyridine-2,3-dicarboxylic acid Chemical class OC(=O)C1=C(C(O)=O)NC=CC1 SYHPGXUWPYJXOO-UHFFFAOYSA-N 0.000 claims 2
- PLHCSZRZWOWUBW-UHFFFAOYSA-N 2-methoxyethyl 3-oxobutanoate Chemical compound COCCOC(=O)CC(C)=O PLHCSZRZWOWUBW-UHFFFAOYSA-N 0.000 claims 2
- HTQOCXMKRPDPOI-UHFFFAOYSA-N 3-o-(2-methoxyethyl) 5-o-propan-2-yl 4-(4-fluorophenyl)-1,2,6-trimethyl-4h-pyridine-3,5-dicarboxylate Chemical compound COCCOC(=O)C1=C(C)N(C)C(C)=C(C(=O)OC(C)C)C1C1=CC=C(F)C=C1 HTQOCXMKRPDPOI-UHFFFAOYSA-N 0.000 claims 2
- 238000007796 conventional method Methods 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- GVIIRWAJDFKJMJ-UHFFFAOYSA-N propan-2-yl 3-oxobutanoate Chemical compound CC(C)OC(=O)CC(C)=O GVIIRWAJDFKJMJ-UHFFFAOYSA-N 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- RKJYCUKWRMKQIH-UHFFFAOYSA-N 3-o-(2-methoxyethyl) 5-o-propan-2-yl 1,2,6-trimethyl-4-[4-(trifluoromethoxy)phenyl]-4h-pyridine-3,5-dicarboxylate Chemical compound COCCOC(=O)C1=C(C)N(C)C(C)=C(C(=O)OC(C)C)C1C1=CC=C(OC(F)(F)F)C=C1 RKJYCUKWRMKQIH-UHFFFAOYSA-N 0.000 claims 1
- PDNSISJOWQICRH-UHFFFAOYSA-N 3-o-(2-methoxyethyl) 5-o-propan-2-yl 1-ethyl-2,6-dimethyl-4-[4-(trifluoromethoxy)phenyl]-4h-pyridine-3,5-dicarboxylate Chemical compound CC(C)OC(=O)C1=C(C)N(CC)C(C)=C(C(=O)OCCOC)C1C1=CC=C(OC(F)(F)F)C=C1 PDNSISJOWQICRH-UHFFFAOYSA-N 0.000 claims 1
- AWIXLXPTWRNXST-UHFFFAOYSA-N 3-o-(2-methoxyethyl) 5-o-propan-2-yl 4-(4-chlorophenyl)-1,2,6-trimethyl-4h-pyridine-3,5-dicarboxylate Chemical compound COCCOC(=O)C1=C(C)N(C)C(C)=C(C(=O)OC(C)C)C1C1=CC=C(Cl)C=C1 AWIXLXPTWRNXST-UHFFFAOYSA-N 0.000 claims 1
- JWDVTJAVBZXALQ-UHFFFAOYSA-N 3-o-(2-methoxyethyl) 5-o-propan-2-yl 4-(4-cyanophenyl)-1,2,6-trimethyl-4h-pyridine-3,5-dicarboxylate Chemical compound COCCOC(=O)C1=C(C)N(C)C(C)=C(C(=O)OC(C)C)C1C1=CC=C(C#N)C=C1 JWDVTJAVBZXALQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 238000007126 N-alkylation reaction Methods 0.000 claims 1
- NSMPDCLKQJRNOO-UHFFFAOYSA-N [Cl].FC#N Chemical compound [Cl].FC#N NSMPDCLKQJRNOO-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 238000013375 chromatographic separation Methods 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- KAOHYMHKNXJUFY-HYXAFXHYSA-N ethyl (z)-2-aminobut-2-enoate Chemical compound CCOC(=O)C(\N)=C\C KAOHYMHKNXJUFY-HYXAFXHYSA-N 0.000 claims 1
- RZTAMFZIAATZDJ-UHFFFAOYSA-N felodipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-UHFFFAOYSA-N 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 235000008216 herbs Nutrition 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
-
- 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
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
- 하기 일반식(I)의 N-알킬화 1,4-디하이드로피리딘디카르복실산 에스테르.상기식에서, R1은 트리플루오로메톡시, 시아노 불소 염소 또는 트리플루오로메틸을 나타내고, R2는 메틸, 에틸 또는 사이클로프로필을 나타내고 단, R1은 R2가 메틸을 나타태는 경우에 트리플루오로메틸을 나타낼 수 없다.
- 라세미체, (+)-또는 (-) 이성체 헝태의 이소프로필 2-메톡시에틸 1,2,6-트리메틸-4-(4-트리플루오로메록시페닐) -1,4-디하이드로피리딘-3,5-디카르복실레이트, 이소프로필 2-메톡시에틸 1, 2, 6-트리메틸-4-(4-시아노페닐)-1.4-디하이드로피리딘-3,5-디카르복실레이트, 이소프로필 2-메톡시에틸 1-에틸-2,6-디메틸-4-(4-트리플루오로메톡시페닐)-1.4-디하이드로피리딘-3,5-디카르복실레이트, 이소프로필 2-메톡시에틸 1,2,6-트리메틸-4-(4-클로로페닐)-1.4-디하이드로피리딘-3,5-디카르복실레이트, 이소프로필 2-메톡시에틸 1,2,6-트리메틸-4- (4-플루오로페닐) -1,4-디하이드로피리딘-3,5-디카르복실레이트, 이소프로필 2-메록시에틸 1-에틸-2,5-디메틸-4-(4-트리플루오로베틸페닐)-1,4-디하이드로피리딘-3,5-디카르복실레이트, 또는 이소프로필 2-메톡시에틸 1-사이클로프로필-2,6-디메틸-4- (4-트리플루오로메록시페닐)-1.4-디하이드로피리딘-3,5-디카르복실레이트인 N-알킬화 1,4-디하이드로피 리딘디카르복실산 에스테르.
- 이소프로필 2-메톡시에틸(土)-1,2,6-트리메틸-4-(4-트리플루오로메록시페닐)-1,4-디하이드로피리딘-3,5-디카르복실레이트, 이소프로필 2-메톡시에틸(+) -1,2,6-트리메틸-4-(4-트리플루오로메톡시페닐)-1.4-디하이드로피리딘-3, 5-디카르복실레이트, 이소프로필 2-메톡시에틸(-)-1,2,6-트리메틸-4-(4-트리플루오로메톡시페닐)-1,4-디하이드로피리딘-3,5-디카르복실레이트, 이소프로필 2-메톡시에틸 (土) -1, 2, 6-트리메틸-4-(4-클로로페닐)-1.4-디하이드로피리딘-3,5-디카르복실레이트, 이소프로필 2-메록시에틸(-)-1,2,6-트리메틸-4-(4-플로로페닐)-1,4-디하이드로피리딘-3,5-디카르복실레이트, 또는 이소프로필 2-메톡시에틸 (-)-1,2,6-트리메틸-4-(4-클로로페닐)-1,4-디하이드로피리딘-3,5-디카르복실레이트인 N-알킬화 1,4-디하이드로피리딘디카르복실산 에스테르.
- 질병 치료용의 제1 내지 3항 중 어느 한 항에 따른 N-알킬화 1,4-디하이드로 피리딘디카르복실산 에스테르.
- [A] 하기 일반식(II)의 알데하이드를 하기 일반식(III)의 이소프로필 아세토아세테이트 또는 하기 일반식 (IV)의 2-메톡시에틸 아세토아세테이트와 반응시키고 임의로 단리시켜서 하기 일반식(V) 또는 (VI)의 대응하는 일리덴 화합물로 전환시키고, 이어서 이 화합물들을 일반식 (V)의 화합물의 경우에는 일반식 (IV)의 2-메톡시 에틸 아세토아세테이트 및 일반식(VI)의 화합물의 경우에는 일반식 (III)의 이소프로필 아세토아세테이트, 및 하기 일반식(VII)의 아민 또는 대응하는 아민 하이드로클로라이드와 불활성 용매 중에서 반응시키거나,(상기식 들에서, R1및 R2는 상기 정의한 바와 같음) [B] R2가 메틸 또는 에틸을 나타내는경우에, 일반식 (V)의 화합물을 하기 일반식 (VIII)의 2-메톡시에틸 아미노크로토네이트와 반응시키거나 또는 일반식 (VI)의 화합물을 하기 일반식(IX)의 2-이소프로필 β-아미노크로토테이트와 불활성 용매중에서 반응시키고, 최종 단계에서 적합하다면 염기의 존재 하에 -NH관능기틀 통상적인 방법에 의하여 알킬화시키고,에난티오머상 순수한 에스테르의 경우에는 크로마토그래피 분리를 직접 수행하거나 또는 임의로 각각의 에난티오머상 순수한 카르복실산을 제조하여 이 화합물을 적합한 경우에 반응성 산 유도체를 경유하여 통상적인 방법에 의하여 에스테르화시키는 것을 특징으로 하는 일반식 (I)의 N-알킬화 1,4-디하이드로피리딘 디카르복실산.상기식에서, R1은 트리플루오로메톡시, 시아노, 불소, 염소 또는 트리플루오로메틸을 나타내고, R2는 메틸, 에틸 또는 사이클로프로필을 나타내고, 단, R1은 R2가 메틸을 나타내는 경우에 트리플루오로메틸을 나타낼 수 없다.
- 제1 내지 3항중 어느 한 항에 따른 N-알킬화 1,4-디하이드로피리딘디카르복실산 에스테르를 1종 이상함유하는 약재.
- N-알킨화 1.4-디하이드로피리딘디카르복신산 에스테르를 적합한 경우에 적합한 보조제 및 부형재를 사용하여 적합한 투여 형태로 전환시키는 것을 특징으로 하는, 제6항에 따른 약제의 제조방법.
- 제1 내지 3항중 어느 한 항에 따른 N-알킬화 1.4-디하이드로피리딘디카르복실산 에스테르의 약재의 제조를 위한 용도.
- 제1 내지 3항중 어느 한 항에 따른 N-알킬화 1,4-디하이드로피리딘디카말복신산 에스테르의 질병 치료를 위한 용도.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4125271.3 | 1991-07-31 | ||
| DE4125271A DE4125271A1 (de) | 1991-07-31 | 1991-07-31 | Neue n-alkylierte 1,4-dihydropyridindicarbonsaeureester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR930002316A true KR930002316A (ko) | 1993-02-22 |
Family
ID=6437351
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019920013669A KR930002316A (ko) | 1991-07-31 | 1992-07-30 | N-알킬화 1,4-디하이드로피리 딘디카르복실산 에스테르 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5328931A (ko) |
| EP (1) | EP0525568B1 (ko) |
| JP (1) | JPH05194395A (ko) |
| KR (1) | KR930002316A (ko) |
| AT (1) | ATE122341T1 (ko) |
| AU (1) | AU646349B2 (ko) |
| CA (1) | CA2074777A1 (ko) |
| CZ (1) | CZ233492A3 (ko) |
| DE (2) | DE4125271A1 (ko) |
| DK (1) | DK0525568T3 (ko) |
| ES (1) | ES2072666T3 (ko) |
| FI (1) | FI923423A (ko) |
| HU (1) | HUT65434A (ko) |
| IE (1) | IE922512A1 (ko) |
| IL (1) | IL102670A0 (ko) |
| MX (1) | MX9204238A (ko) |
| NO (1) | NO177094B (ko) |
| ZA (1) | ZA925726B (ko) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4342196A1 (de) * | 1993-12-10 | 1995-06-14 | Bayer Ag | Neue 4-Phenyl-substituierte 1,4-Dihydropyridine |
| ES2096179T3 (es) * | 1992-10-30 | 1997-03-01 | Bayer Ag | Dihidropiridinas sustituidas en la posicion 4 con un heterociclilfenilo. |
| EE03192B1 (et) * | 1993-12-10 | 1999-06-15 | Bayer Aktiengesellschaft | Isopropüül-(2-metoksüetüül)-4-(2-kloro-3-tsüanofenüül)-1,4-dihüdro-2,6-dimetüülpüri diin-3,5-dikarboksülaat, selle enantiomeerid ja vaheühend, meetodid nimetatud ühendite valmistamiseks ja kasutamine |
| DE4342193A1 (de) * | 1993-12-10 | 1995-06-14 | Bayer Ag | Arylsubstituierte Alkoxycarbonyl-1,4-dihydropyridin-5-carbonsäureester |
| DE4342195A1 (de) * | 1993-12-10 | 1995-06-14 | Bayer Ag | Dihydropyridine mit heterocyclisch substituierten Estern |
| DK0657432T3 (da) | 1993-12-10 | 2003-07-07 | Bayer Ag | Phenylsubstituerede 1,4-dihydropyridiner med cerebral aktivitet |
| DE4430092A1 (de) * | 1994-08-25 | 1996-02-29 | Bayer Ag | 2,3-Cyclisch kondensierte 1,4-Dihydropyridine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| WO2003099790A1 (en) * | 2002-05-29 | 2003-12-04 | Council Of Scientific And Industrial Research | Process for the preparation of 1,4-dihydropyridines and novel 1,4-dihydropyridines useful as therapeutic agents |
| US11512052B2 (en) | 2017-11-21 | 2022-11-29 | Icahn School Of Medicine At Mount Sinai | Dihydropyridines for the treatment of cognitive impairment or traumatic brain injury |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1923990C3 (de) * | 1969-05-10 | 1978-11-23 | Bayer Ag | Verfahren zur Herstellung von N-substituierten M-Dihydropyridin-S.S-dicarbonsäureestern |
| DE1963188A1 (de) * | 1969-12-17 | 1971-06-24 | Bayer Ag | Neue Cyanphenyl-1,4-dihydropyridinderivate |
| DE2210667A1 (de) * | 1972-03-06 | 1973-09-20 | Bayer Ag | Kondensiert aromatisch substituierte 1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE2210672C3 (de) * | 1972-03-06 | 1980-03-20 | Bayer Ag, 5090 Leverkusen | N-substituierte unsymmetrische 1 ^-Dihydropyridin-S^-dicarbonsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
| DE2508181A1 (de) * | 1975-02-26 | 1976-09-09 | Bayer Ag | 1,4-dihydropyridincarbonsaeurearal- kylester, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US4284634A (en) * | 1975-07-02 | 1981-08-18 | Fujisawa Pharmaceutical Co., Ltd. | 1,4-Dihydropyridine derivatives, and pharmaceutical method of the same |
| DK142287A (da) * | 1986-03-27 | 1987-09-28 | Byk Gulden Lomberg Chem Fab | Optisk aktive 1,4-dihydropyridinderivater |
| FR2596760B1 (fr) * | 1986-04-02 | 1988-12-09 | Sori Soc Rech Ind | Derives dissymetriques de l'acide 1,4-dihydropyridine-3,5-dicarboxylique, procedes de preparation et utilisation en therapeutique |
| EP0322747B1 (en) * | 1987-12-29 | 1994-03-02 | Fujisawa Pharmaceutical Co., Ltd. | A brain neuron protecting agent containing a dihydropyridine compound |
| AU650567B2 (en) * | 1988-09-06 | 1994-06-23 | Davis, Warren L. | Dental syringe tip and adaptor |
| DE4011695A1 (de) * | 1990-04-11 | 1991-10-17 | Bayer Ag | Verwendung von n-alkylierten 1,4-dihydropyridindicarbonsaeureestern als arzneimittel, neue verbindungen und verfahren zu ihrer herstellung |
-
1991
- 1991-07-31 DE DE4125271A patent/DE4125271A1/de not_active Withdrawn
-
1992
- 1992-07-17 NO NO922852A patent/NO177094B/no unknown
- 1992-07-20 AT AT92112355T patent/ATE122341T1/de not_active IP Right Cessation
- 1992-07-20 ES ES92112355T patent/ES2072666T3/es not_active Expired - Lifetime
- 1992-07-20 DK DK92112355.0T patent/DK0525568T3/da active
- 1992-07-20 EP EP92112355A patent/EP0525568B1/de not_active Expired - Lifetime
- 1992-07-20 MX MX9204238A patent/MX9204238A/es not_active IP Right Cessation
- 1992-07-20 DE DE59202132T patent/DE59202132D1/de not_active Expired - Fee Related
- 1992-07-21 US US07/917,565 patent/US5328931A/en not_active Expired - Fee Related
- 1992-07-22 AU AU20483/92A patent/AU646349B2/en not_active Ceased
- 1992-07-24 CZ CS922334A patent/CZ233492A3/cs unknown
- 1992-07-28 CA CA002074777A patent/CA2074777A1/en not_active Abandoned
- 1992-07-29 IL IL102670A patent/IL102670A0/xx unknown
- 1992-07-29 FI FI923423A patent/FI923423A/fi unknown
- 1992-07-29 JP JP4220979A patent/JPH05194395A/ja active Pending
- 1992-07-30 HU HU9202489A patent/HUT65434A/hu unknown
- 1992-07-30 IE IE251292A patent/IE922512A1/en not_active Application Discontinuation
- 1992-07-30 KR KR1019920013669A patent/KR930002316A/ko not_active Application Discontinuation
- 1992-07-30 ZA ZA925726A patent/ZA925726B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO922852L (no) | 1993-02-01 |
| ES2072666T3 (es) | 1995-07-16 |
| AU2048392A (en) | 1993-02-04 |
| IE922512A1 (en) | 1993-02-10 |
| NO177094B (no) | 1995-04-10 |
| ATE122341T1 (de) | 1995-05-15 |
| HUT65434A (en) | 1994-06-28 |
| FI923423A0 (fi) | 1992-07-29 |
| DK0525568T3 (da) | 1995-10-09 |
| MX9204238A (es) | 1993-01-01 |
| DE59202132D1 (de) | 1995-06-14 |
| EP0525568A1 (de) | 1993-02-03 |
| IL102670A0 (en) | 1993-01-14 |
| AU646349B2 (en) | 1994-02-17 |
| FI923423A (fi) | 1993-02-01 |
| CA2074777A1 (en) | 1993-02-01 |
| NO922852D0 (no) | 1992-07-17 |
| HU9202489D0 (en) | 1992-10-28 |
| JPH05194395A (ja) | 1993-08-03 |
| ZA925726B (en) | 1993-03-10 |
| EP0525568B1 (de) | 1995-05-10 |
| US5328931A (en) | 1994-07-12 |
| CZ233492A3 (en) | 1993-05-12 |
| DE4125271A1 (de) | 1993-02-11 |
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