KR930006006A - 치환된 피리디닐아미노-1H-인돌, 1H-인다졸, 2H-인디졸, 벤조[b]티오펜 및 1,2-벤즈이소티아졸, 이들의 제조방법 및 약제로서의 이들의 용도 - Google Patents
치환된 피리디닐아미노-1H-인돌, 1H-인다졸, 2H-인디졸, 벤조[b]티오펜 및 1,2-벤즈이소티아졸, 이들의 제조방법 및 약제로서의 이들의 용도 Download PDFInfo
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- KR930006006A KR930006006A KR1019920017238A KR920017238A KR930006006A KR 930006006 A KR930006006 A KR 930006006A KR 1019920017238 A KR1019920017238 A KR 1019920017238A KR 920017238 A KR920017238 A KR 920017238A KR 930006006 A KR930006006 A KR 930006006A
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- lower alkyl
- compound
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- 239000003814 drug Substances 0.000 title claims 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title abstract 4
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical class C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 title abstract 4
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 title abstract 2
- JULKLMOOTJHVHH-UHFFFAOYSA-N n-pyridin-2-ylindol-1-amine Chemical class C1=CC2=CC=CC=C2N1NC1=CC=CC=N1 JULKLMOOTJHVHH-UHFFFAOYSA-N 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract 19
- 150000001875 compounds Chemical class 0.000 claims abstract 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 13
- 239000001257 hydrogen Substances 0.000 claims abstract 13
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract 10
- 125000003118 aryl group Chemical group 0.000 claims abstract 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 6
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims abstract 6
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 5
- 239000002253 acid Substances 0.000 claims abstract 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 4
- 150000002367 halogens Chemical class 0.000 claims abstract 4
- 150000003839 salts Chemical class 0.000 claims abstract 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 3
- 125000002252 acyl group Chemical group 0.000 claims abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 2
- 208000017520 skin disease Diseases 0.000 claims abstract 2
- MIUDFPNJBRWIJC-UHFFFAOYSA-N 1-methyl-n-propyl-n-pyridin-4-ylindol-5-amine Chemical compound C=1C=C2N(C)C=CC2=CC=1N(CCC)C1=CC=NC=C1 MIUDFPNJBRWIJC-UHFFFAOYSA-N 0.000 claims 1
- ABFCZHBVZMUKSP-UHFFFAOYSA-N 1-methyl-n-pyridin-4-ylindol-5-amine Chemical compound C=1C=C2N(C)C=CC2=CC=1NC1=CC=NC=C1 ABFCZHBVZMUKSP-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000005418 aryl aryl group Chemical group 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 150000005748 halopyridines Chemical class 0.000 claims 1
- -1 hydrogen Compound Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000007074 memory dysfunction Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridine hydrochloride Substances [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims 1
- 208000004481 Choline Deficiency Diseases 0.000 abstract 1
- 206010061218 Inflammation Diseases 0.000 abstract 1
- 208000026139 Memory disease Diseases 0.000 abstract 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 abstract 1
- 208000021752 choline deficiency disease Diseases 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 230000004064 dysfunction Effects 0.000 abstract 1
- 230000004054 inflammatory process Effects 0.000 abstract 1
- 239000002858 neurotransmitter agent Substances 0.000 abstract 1
- 230000002474 noradrenergic effect Effects 0.000 abstract 1
- 230000000862 serotonergic effect Effects 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
Classifications
-
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
본 발명은 일반식(Ⅰ)의 치환된 피리디닐아미노-1H-인돌, 1H-인다졸, 2H-인다졸, 벤조[b]티오펜 및 1,2-벤즈이소티아졸 또는 이들의 약제학적으로 허용되는 산 부가염에 관한 것이다.
상기식에서, Q는 S, N 또는 NR2이고, Y는 CH, N 또는 NR2이고, R1은 수소, 저급알킬, 저급알키닐, 저급알케닐, 아릴저급알킬, 저급알콕시카보닐아미노저급알킬카보닐, 아릴저급알콕시카보닐아미노저급알킬카보닐, 아미노저급알킬카보닐, 저급알콕시카보닐 또는 아실이고, R2은 수소 또는 저급알킬이고, R3은 수소 또는 저급알킬이고, X는 수소, 저급알킬 또는 할로겐이고, n은 0 또는 1이다. 본 발명의 화합물은 알쯔하이머 병(Alzhimer's disease) 및 기타 기억질환(memory disorders)과 관련된 타임과 같은 콜린 결핍으로 특성화되는 기억 역기능(onemeory dysfunction)[예 : 강박반응 장해(obsessive compulsive disorder]의 치료용으로 유용한 노르아드레날린성(noradrenergic) and 세로토닌성(serotonergic)과 같은 신경전달물질 작용의 변조제로서의 유용성을 갖는다. 부가적으로, 본 발명의 화합물은 다양한 피부병의 치료를 위한 국소 함염증세로서 유용하다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 일반식(Ⅰ)의 화합물 또는 이의 약학제적으로 허용되는 산 부가염.상기식에서, Q는 S, N 또는 NR2이고, Y는 CH, N 또는 NR2이고, R1은 수소, 저급알킬, 저급알키닐, 저급알케닐, 아릴저급알킬, 저급알콕시카보닐아미노저급알킬카보닐, 아릴저급알콕시카보닐-아미노저급알킬카보닐, 아미노저급알킬카보닐, 저급아콕시카보닐 또는 아실이고, R2은 수소 또는 저급알킬이고, R3은 수소 또는 저급알킬이고, X는 수소, 저급알킬 또는 할로겐이고, n은 0 또는 1이다.
- 제1항에 있어서, Y가 CH 또는 N이고 Q는 NR2인 화합물
- 제2항에 있어서, R3가 수소이고, X가 수소이고 n은 0인 화합물.
- 제3항에 있어서, R1이 수소, 저급알킬, 저급알콕시카보닐 또는 아릴저급알콕시카보닐아미노저급알킬카보닐인 화합물.
- 제4항에 있어서, Y가 CH인 화합물.
- 제1항에 있어서, 1-메틸-5-(4-피리딜아미노)-1H-인돌인 화합물 또는 이의 약제학적으로 허용되는 산 부가염.
- 제1항에 있어서, 1-메틸-5-(프로필-4-피리딜아미노)-1H-인돌인 화합물 또는 이의 약제학적으로 허용되는 산 부가염.
- 활성 성분으로서 제1항의 일반식(Ⅰ)의 화합물 및 이를 위한 약제학적으로 허용되는 적당한 담체를 포함하는 약제학적 조성물.
- 기억 기능장해, 우울증, 성격 장해(personaliy disorder) 및 피부병의 치료에서 유효한 약제를 제조하기 위한 제1항의 일반식(Ⅰ)의 화합물의 용도.
- a) 일반식(Ⅱ)의 화합물을 일반식(Ⅵ)의 할로피리딘 하이드로클로라이드와 반응시키거나, b) 일반식(Ⅰ)(이때, R1은 수소이다)의 화합물을 일반식 R7Hal(이때, R7은 저급알킬, 저급알케닐, 저급알키닐 또는 아릴저급알킬이다)의 화합물로 임의로 알킬화하여 일반식(Ⅰ)(이때, Q, Y, R2, R3, X 및 n은 제1항에서 정의된 바와 같고 R1은 저급 알킬, 저급 알케닐, 저급 알키닐 또는 아릴저급알킬이다)의 화합물을 형성시키거나, c) 일반식(Ⅰ)(이때, R1은 수소이다)의 화합물을(이때, Z는 할로겐이고, R′1는 저급알킬, 저급알키닐, 저급알케닐, 아릴 또는 아릴 저급알킬이다)의 화합물로 임의로 아실화하여 일반식(Ⅰ)(이때, Q, Y, R2, R3, X 및 n은 제1항에서 정의된 바와 같고, R1은 저급 알킬, 저급 알케닐, 저급 알키닐, 아릴, 아릴저급알킬이다)의 화합물을 형성시키거나, d) 일반식(Ⅰ)(이때, Q, Y, R2, R3, X 및 n은 제1항에서 정의된 바와 같고 R1은 저급알콕시카보닐아미노저급알킬카보닐 또는 아릴저급알콕시카보닐아미노저급알킬카보닐이다)의 화합물을 형성시키거나, e) 상기 단계 d)에서 수독된 바와 같은 일반식(Ⅰ)의 화합물을 임의로 가수분해시켜 일반식(Ⅰ)(이때, QYR2, R3, X 및 n은 상기 정의된 바와 같고 R1은 아미노 저급알킬카보닐이다)의 화합물을 형성시킴을 특징으로 하여, 제1항의 일반식(Ⅰ)의 화합물을 제조하는 방법.상기식에서, Q, Y, R3, X 및 n은 제1항에서 정의된 바와 같고, Hal은 할로겐이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/764,031 | 1991-09-23 | ||
| US07/764,031 US5185350A (en) | 1991-09-23 | 1991-09-23 | Substituted pyridinylamino-1h-indoles,1h-indazoles,2h-indazoles, benzo (b)thiophenes and 1,2-benzisothiazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR930006006A true KR930006006A (ko) | 1993-04-20 |
Family
ID=25069502
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019920017238A Withdrawn KR930006006A (ko) | 1991-09-23 | 1992-09-22 | 치환된 피리디닐아미노-1H-인돌, 1H-인다졸, 2H-인디졸, 벤조[b]티오펜 및 1,2-벤즈이소티아졸, 이들의 제조방법 및 약제로서의 이들의 용도 |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US5185350A (ko) |
| EP (1) | EP0534343B1 (ko) |
| JP (1) | JP2961023B2 (ko) |
| KR (1) | KR930006006A (ko) |
| AT (1) | ATE160346T1 (ko) |
| AU (1) | AU653263B2 (ko) |
| CA (1) | CA2078814C (ko) |
| CZ (1) | CZ290692A3 (ko) |
| DE (1) | DE69223205T2 (ko) |
| DK (1) | DK0534343T3 (ko) |
| ES (1) | ES2111025T3 (ko) |
| FI (1) | FI924230L (ko) |
| GR (1) | GR3025774T3 (ko) |
| HU (1) | HUT64055A (ko) |
| IL (1) | IL103232A0 (ko) |
| MX (1) | MX9205374A (ko) |
| NO (1) | NO923686L (ko) |
| TW (1) | TW207539B (ko) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20230027814A (ko) * | 2021-08-20 | 2023-02-28 | 김수영 | 포켓 인슐레이터 및 이를 포함하는 단열체 |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0550507A1 (en) * | 1990-09-13 | 1993-07-14 | Beecham Group p.l.c. | Indole ureas as 5 ht receptor antagonist |
| US5356910A (en) | 1993-07-19 | 1994-10-18 | Hoechst-Roussel Pharmaceuticals Inc. | Use of N-(pyridinyl)-1H-indol-1-amines for the treatment of obsessive-compulsive disorder |
| EP0735821A4 (en) * | 1993-12-21 | 1998-04-01 | Lilly Co Eli | METHODS FOR TREATING OR PREVENTING CONDITIONS ASSOCIATED WITH AMYLO DOGEN PEPTIDES |
| DE19626373A1 (de) * | 1996-07-02 | 1998-01-08 | Boehringer Ingelheim Kg | Neuartige Verwendung von Wirkstoffen, welche die Funktion von nichtneuronalem Acetylcholin beeinflussen |
| TW200302722A (en) * | 2002-02-13 | 2003-08-16 | Astrazeneca Ab | Therapeutic agents |
| US20050222123A1 (en) | 2004-01-27 | 2005-10-06 | North Shore-Long Island Jewish Research Institute | Cholinesterase inhibitors for treating inflammation |
| US7592357B2 (en) * | 2004-02-20 | 2009-09-22 | Smithkline Beecham Corporation | Compounds |
| JP4787471B2 (ja) * | 2004-05-21 | 2011-10-05 | 株式会社ポッカコーポレーション | 脳機能亢進剤 |
| BRPI0511722A (pt) | 2004-06-01 | 2008-01-08 | Hoffmann La Roche | 3-amino-1-arilpropilindóis como inibidores da recaptação de monoamina |
| BRPI0619263A2 (pt) | 2005-11-30 | 2011-09-27 | Hoffmann La Roche | indóis de 3-amino-1-arilpropila e indóis aza-substituìdos, métodos para prepará-los, composição farmacêutica e uso dos referidos indóis |
| RU2008120141A (ru) | 2005-11-30 | 2010-01-10 | Ф. Хоффманн-Ля Рош Аг (Ch) | 3-амино-2-арилпропилазаиндолы и их применения |
| EP2351737A1 (en) * | 2005-11-30 | 2011-08-03 | F. Hoffmann-La Roche AG | 3-Amino-1-arylpropyl indoles and aza-substituted indoles |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3852335T2 (de) * | 1987-04-24 | 1995-05-11 | Hoechst Roussel Pharma | N-(Pyridinyl)-1H-indol-1-amine, Verfahren zu deren Herstellung und ihre Verwendung als Arzneimittel. |
| US4983615A (en) * | 1989-06-28 | 1991-01-08 | Hoechst-Roussel Pharmaceuticals Inc. | Heteroarylamino- and heteroaryloxypyridinamine compounds which are useful in treating skin disorders |
| US4970219A (en) * | 1989-06-28 | 1990-11-13 | Hoechst-Roussel Pharmaceuticals Inc. | Heteroarylamino- and heteroaryloxypyridinamine compounds which have useful utility in treating skin disorders |
| US5006537A (en) * | 1989-08-02 | 1991-04-09 | Hoechst-Roussel Pharmaceuticals, Inc. | 1,3-dihydro-1-(pyridinylamino)-2H-indol-2-ones |
| US5177088A (en) * | 1991-04-17 | 1993-01-05 | Hoechst-Roussel Pharmaceuticals Incorporated | Substituted 3-(pyridinylamino)-indoles |
-
1991
- 1991-09-23 US US07/764,031 patent/US5185350A/en not_active Expired - Fee Related
-
1992
- 1992-09-10 TW TW081107145A patent/TW207539B/zh active
- 1992-09-21 IL IL103232A patent/IL103232A0/xx unknown
- 1992-09-21 EP EP92116110A patent/EP0534343B1/en not_active Expired - Lifetime
- 1992-09-21 DK DK92116110T patent/DK0534343T3/da active
- 1992-09-21 FI FI924230A patent/FI924230L/fi unknown
- 1992-09-21 AT AT92116110T patent/ATE160346T1/de not_active IP Right Cessation
- 1992-09-21 DE DE69223205T patent/DE69223205T2/de not_active Expired - Fee Related
- 1992-09-21 ES ES92116110T patent/ES2111025T3/es not_active Expired - Lifetime
- 1992-09-22 NO NO92923686A patent/NO923686L/no unknown
- 1992-09-22 MX MX9205374A patent/MX9205374A/es not_active IP Right Cessation
- 1992-09-22 JP JP4251779A patent/JP2961023B2/ja not_active Expired - Fee Related
- 1992-09-22 HU HU9203023A patent/HUT64055A/hu unknown
- 1992-09-22 AU AU25297/92A patent/AU653263B2/en not_active Expired - Fee Related
- 1992-09-22 KR KR1019920017238A patent/KR930006006A/ko not_active Withdrawn
- 1992-09-22 CA CA002078814A patent/CA2078814C/en not_active Expired - Lifetime
- 1992-09-22 CZ CS922906A patent/CZ290692A3/cs unknown
-
1993
- 1993-03-25 US US08/038,317 patent/US5328918A/en not_active Expired - Lifetime
-
1997
- 1997-12-23 GR GR970403425T patent/GR3025774T3/el unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20230027814A (ko) * | 2021-08-20 | 2023-02-28 | 김수영 | 포켓 인슐레이터 및 이를 포함하는 단열체 |
Also Published As
| Publication number | Publication date |
|---|---|
| FI924230L (fi) | 1993-03-24 |
| HU9203023D0 (en) | 1993-11-29 |
| JP2961023B2 (ja) | 1999-10-12 |
| FI924230A0 (fi) | 1992-09-21 |
| US5328918A (en) | 1994-07-12 |
| MX9205374A (es) | 1993-03-01 |
| EP0534343B1 (en) | 1997-11-19 |
| DK0534343T3 (da) | 1998-07-27 |
| DE69223205D1 (de) | 1998-01-02 |
| GR3025774T3 (en) | 1998-03-31 |
| JPH061787A (ja) | 1994-01-11 |
| CZ290692A3 (en) | 1993-04-14 |
| HUT64055A (en) | 1993-11-29 |
| TW207539B (ko) | 1993-06-11 |
| CA2078814C (en) | 2003-09-09 |
| IL103232A0 (en) | 1993-02-21 |
| EP0534343A1 (en) | 1993-03-31 |
| CA2078814A1 (en) | 1993-03-24 |
| NO923686D0 (no) | 1992-09-22 |
| US5185350A (en) | 1993-02-09 |
| DE69223205T2 (de) | 1998-05-14 |
| AU653263B2 (en) | 1994-09-22 |
| ATE160346T1 (de) | 1997-12-15 |
| NO923686L (no) | 1993-03-24 |
| ES2111025T3 (es) | 1998-03-01 |
| AU2529792A (en) | 1993-03-25 |
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