KR950000691A - 피페리딘 및 피페라진 - Google Patents
피페리딘 및 피페라진 Download PDFInfo
- Publication number
- KR950000691A KR950000691A KR1019940014712A KR19940014712A KR950000691A KR 950000691 A KR950000691 A KR 950000691A KR 1019940014712 A KR1019940014712 A KR 1019940014712A KR 19940014712 A KR19940014712 A KR 19940014712A KR 950000691 A KR950000691 A KR 950000691A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- piperidine
- compound
- dimethoxyphenyl
- ethyl
- Prior art date
Links
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title claims abstract 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 8
- 150000003839 salts Chemical class 0.000 claims abstract 8
- 150000004885 piperazines Chemical class 0.000 claims abstract 3
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 claims abstract 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 125000003435 aroyl group Chemical group 0.000 claims abstract 2
- 125000001589 carboacyl group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 10
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- QSUOQHYSEGYJDT-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)piperidine Chemical compound C1=C(OC)C(OC)=CC=C1N1CCCCC1 QSUOQHYSEGYJDT-UHFFFAOYSA-N 0.000 claims 1
- ANKUIEIRICWRAW-UHFFFAOYSA-N 1-[2-(2,3-dihydro-1-benzofuran-3-yl)ethyl]-4-(3,4-dimethoxyphenyl)piperidine Chemical compound C1=C(OC)C(OC)=CC=C1C1CCN(CCC2C3=CC=CC=C3OC2)CC1 ANKUIEIRICWRAW-UHFFFAOYSA-N 0.000 claims 1
- PNAWYAFVBUDGHL-UHFFFAOYSA-N 1-[2-(2,3-dihydro-1h-inden-1-yl)ethyl]-4-(3,4-dimethoxyphenyl)piperidine Chemical compound C1=C(OC)C(OC)=CC=C1C1CCN(CCC2C3=CC=CC=C3CC2)CC1 PNAWYAFVBUDGHL-UHFFFAOYSA-N 0.000 claims 1
- YYMRBZIDVSLGND-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-1-[2-(2,3,4,5-tetrahydro-1-benzoxepin-5-yl)ethyl]piperidine Chemical compound C1=C(OC)C(OC)=CC=C1C1CCN(CCC2C3=CC=CC=C3OCCC2)CC1 YYMRBZIDVSLGND-UHFFFAOYSA-N 0.000 claims 1
- SDCAITOWCWHTSR-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-1-[2-(6,7,8,9-tetrahydro-5h-benzo[7]annulen-5-yl)ethyl]piperidine Chemical compound C1=C(OC)C(OC)=CC=C1C1CCN(CCC2C3=CC=CC=C3CCCC2)CC1 SDCAITOWCWHTSR-UHFFFAOYSA-N 0.000 claims 1
- RYWVNFXYVITQIV-UHFFFAOYSA-N 4-[2-[4-(3,4-dimethoxyphenyl)piperidin-1-yl]ethyl]-1,2,3,4-tetrahydroquinoline Chemical compound C1=C(OC)C(OC)=CC=C1C1CCN(CCC2C3=CC=CC=C3NCC2)CC1 RYWVNFXYVITQIV-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 238000010306 acid treatment Methods 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 150000007514 bases Chemical class 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- -1 tetralin-1-yl Chemical group 0.000 claims 1
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Quinoline Compounds (AREA)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
Abstract
하기 일반식(Ⅰ)의 피페리딘 및 피페라진 유도체 및 그의 생리학적으로 허용가능한 염은 항부정맥 효과를 나타낸다 :
상기식에서, R1및 R2는 H 또는 A이고, R3,R4및 R5는 각각의 경우 서로 독립적으로 H,Hal,OH,OA,OAc,NO2,NH2,NHAc,NHSO2A 또는 CN이거나, 또는 R3및 R4는 함께 또한 -O-(CH2)m-O-이고, n은 0,1 또는 2이고, X는 만약 n이 0 또는 2이면, O 또는 CH2이거나, 또는 만약 n이 1이면, CH2,NH,NA 또는 NAc이고, Y는 CH 또는 N이고, m은 1 또는 2이고, Hal은 F,Cl,Br 또는 I이고, A는 탄소수 1 내지 6의 알킬이며, Ac는 탄소수 14 내지 8의 알카노일, 탄소수 1 내지 10의 아르알카노일 또는 탄소수 7 내지 11의 아로일이다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (8)
- 하기 일반식(Ⅰ)의 피페리딘 및 피페라진 유도체 및 그의 약학적으로 허용가능한 염 :상기식에서, R1및 R2는 H 또는 A이고, R3,R4및 R5는 각각의 경우 서로 독립적으로 H,Hal,OH,OA,OAc,NO2,NH2,NHAc,NHSO2A 또는 CN이거나, 또는 R3및 R4는 함께 또한 -O-(CH2)m-O-이고, n은 0,1 또는 2이고, X는 만약 n이 0 또는 2이면, O 또는 CH2이거나, 또는 만약 n이 1이면, CH2,NH,NA 또는 NAc이고, Y는 CH 또는 N이고, m은 1 또는 2이고, Hal은 F,Cl,Br 또는 I이고, A는 탄소수 1 내지 6의 알킬이며, Ac는 탄소수 14 내지 8의 알카노일, 탄소수 1 내지 10의 아르알카노일 또는 탄소수 7 내지 11의 아로일이다.
- 제 1 항에 따라는 일반식(Ⅰ) 화합물의 거울상이성체.
- (a) 1-[2-(6,7,8,9-테트라하이드로-5H-벤조사이클로헵텐-5-일)에틸]-4-(3,4-디메톡시페닐)피페리딘; (b) 5-[2-(4-(3,4-디메톡시페닐)-1-피페리디닐)-에틸]-2,3,4,5-테트라하이드로-1-벤조옥세핀; (c) 3-[2-(4-(3,4-디메톡시페닐)-1-피페리디닐)-에틸]-2,3-디하이드로벤조푸란; (d) 1-[2-(테트랄린-1-일)-에틸]-4,(3,4-디메톡시페닐)피페리딘; (e) 1-[2-(인단-1-일)-에틸]-4-(3,4-디메톡시페닐)피페리딘 ; (f) 1-[2-(1,2,3,4-테트라하이드로퀴놀린-4-일)에틸]-4-(3,4-디메톡시페닐)피페리딘 및 그의 염.
- 하기 일반식(Ⅱ)의 화합물을 하기 일반식(Ⅲ)의 화합물과 반응시키거나, 또는 하나 이상의 CH2그룹 대신에 하나 이상의 환원성 그룹을 가짐을 제외하고는, 그 자체로 일반식(Ⅰ)에 상응하는 화합물을 환원에 의해 일반식(Ⅰ)의 화합물로 전환시키고/시키거나, 일반식(Ⅰ)의 화합물에서 각각 하나 이상의 라디칼 R3, R4및/또는 R5또는 X(X=NH일 경우)를 각각 다른 라디칼 R3, R4및/또는 R5또는 X로 전환시키고/시키거나, 일반식(Ⅰ)의 염기성 화합물을 산 처리에 의해 그의 생리학적으로 허용가능한 산 부가 염중의 하나로 전환시킴을 특징으로 하는, 제 1 항에 따르는 일반식(Ⅰ)의 피페리딘 및 피페라진 유도체의 제조방법;상기식에서, Z는 Cl,Br,OH 또는 반응식으로, 작용기가 변형된 OH 그룹이고, R1,R2,R3,R4,R5,X,Y 및 n은 제 1 항에 언급된 정의와 동일하다.
- 일반식(Ⅰ)의 화합물 및/또는 그의 생리학적으로 허용가능한 염중의 하나를 하나 이상의 고체, 액체 또는 반고체 부형제 또는 보조제와 함께 적합한 투여형으로 제공함을 특징으로 하는, 약학 제제의 제조방법.
- 하나 이상의 일반식(Ⅰ)의 화합물 및/또는 그의 생리학적으로 허용가능한 염중의 하나를 함유함을 특징으로 하는, 약학 제제.
- 약물을 제조하기 위한, 제 1 항에 따르는 일반식(Ⅰ)의 화합물 또는 그의 생리학적으로 허용가능한 염의 용도.
- 질병 치료에 있어서의 제 1 항에 따르는 일반식(Ⅰ)의 화합물 또는 그의 생리학적으로 허용가능한 염의 용도.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP4321366.9 | 1993-06-26 | ||
DE4321366A DE4321366A1 (de) | 1993-06-26 | 1993-06-26 | Piperidine und Piperazine |
Publications (1)
Publication Number | Publication Date |
---|---|
KR950000691A true KR950000691A (ko) | 1995-01-03 |
Family
ID=6491352
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019940014712A KR950000691A (ko) | 1993-06-26 | 1994-06-25 | 피페리딘 및 피페라진 |
Country Status (16)
Country | Link |
---|---|
US (1) | US5495022A (ko) |
EP (1) | EP0634398A1 (ko) |
JP (1) | JPH0725851A (ko) |
KR (1) | KR950000691A (ko) |
CN (1) | CN1102649A (ko) |
AU (1) | AU6487294A (ko) |
CA (1) | CA2126719A1 (ko) |
CZ (1) | CZ155994A3 (ko) |
DE (1) | DE4321366A1 (ko) |
HU (1) | HUT70834A (ko) |
NO (1) | NO942411L (ko) |
PL (1) | PL303978A1 (ko) |
RU (1) | RU94022271A (ko) |
SK (1) | SK77494A3 (ko) |
TW (1) | TW293818B (ko) |
ZA (1) | ZA944573B (ko) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2188949A1 (en) * | 1994-04-28 | 1995-11-09 | Janusz Jozef Kulagowski | Benzofuran derivatives as d4 receptor antagonists |
FR2734819B1 (fr) * | 1995-05-31 | 1997-07-04 | Adir | Nouveaux composes de la piperazine, de la piperidine et de la 1,2,5,6-tetrahydropyridine, leur procede de preparation et les compositions pharmaceutiques les contenant |
AU7261196A (en) * | 1995-10-10 | 1997-04-30 | Eli Lilly And Company | N-{2-substituted-3-(2-aminoethyl)-1h-indol-5-yl}-amides: new 5-ht1f agonists |
GB9521347D0 (en) * | 1995-10-18 | 1995-12-20 | Merck Sharp & Dohme | Therapeutic agents |
GB9912410D0 (en) | 1999-05-28 | 1999-07-28 | Pfizer Ltd | Compounds useful in therapy |
ES2806408T3 (es) * | 2013-12-20 | 2021-02-17 | Esteve Pharmaceuticals Sa | Compuestos piperidínicos con actividad multimodal contra el dolor |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4302589A (en) * | 1980-05-08 | 1981-11-24 | American Cyanamid Company | Cis-mono and disubstituted-2-methyl-3-[(piperazinyl) and (piperidino)ethyl]indolines, intermediates for their preparation and methods of preparation |
FR2618437B1 (fr) * | 1987-07-23 | 1989-11-17 | Rhone Poulenc Sante | Nouveaux derives du benzopyranne, leur preparation et les medicaments qui les contiennent |
FR2670491B1 (fr) * | 1990-12-14 | 1993-02-05 | Adir | Nouvelles piperazines 1,4-disubstituees, leur procede de preparation et les compositions pharmaceutiques les renfermant. |
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1993
- 1993-06-26 DE DE4321366A patent/DE4321366A1/de not_active Withdrawn
-
1994
- 1994-04-24 RU RU94022271/04A patent/RU94022271A/ru unknown
- 1994-06-14 EP EP94109058A patent/EP0634398A1/de not_active Withdrawn
- 1994-06-20 JP JP6136940A patent/JPH0725851A/ja active Pending
- 1994-06-22 AU AU64872/94A patent/AU6487294A/en not_active Abandoned
- 1994-06-24 US US08/264,872 patent/US5495022A/en not_active Expired - Fee Related
- 1994-06-24 NO NO942411A patent/NO942411L/no unknown
- 1994-06-24 PL PL94303978A patent/PL303978A1/xx unknown
- 1994-06-24 HU HU9401914A patent/HUT70834A/hu unknown
- 1994-06-24 CA CA002126719A patent/CA2126719A1/en not_active Abandoned
- 1994-06-24 CZ CZ941559A patent/CZ155994A3/cs unknown
- 1994-06-24 CN CN94106806A patent/CN1102649A/zh active Pending
- 1994-06-24 ZA ZA944573A patent/ZA944573B/xx unknown
- 1994-06-24 TW TW083105752A patent/TW293818B/zh active
- 1994-06-25 KR KR1019940014712A patent/KR950000691A/ko not_active Application Discontinuation
- 1994-06-27 SK SK774-94A patent/SK77494A3/sk unknown
Also Published As
Publication number | Publication date |
---|---|
DE4321366A1 (de) | 1995-01-05 |
NO942411L (no) | 1994-12-27 |
NO942411D0 (ko) | 1994-06-24 |
CA2126719A1 (en) | 1994-12-27 |
HUT70834A (en) | 1995-11-28 |
JPH0725851A (ja) | 1995-01-27 |
CZ155994A3 (en) | 1995-10-18 |
US5495022A (en) | 1996-02-27 |
EP0634398A1 (de) | 1995-01-18 |
TW293818B (ko) | 1996-12-21 |
PL303978A1 (en) | 1995-01-09 |
SK77494A3 (en) | 1995-07-11 |
CN1102649A (zh) | 1995-05-17 |
HU9401914D0 (en) | 1994-09-28 |
AU6487294A (en) | 1995-01-05 |
ZA944573B (en) | 1995-02-14 |
RU94022271A (ru) | 1996-04-20 |
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