KR910009714A - 면역자극성 6-아릴-5,6-디하이드로이미다조[2,1-b]티아졸 유도체 - Google Patents
면역자극성 6-아릴-5,6-디하이드로이미다조[2,1-b]티아졸 유도체 Download PDFInfo
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- KR910009714A KR910009714A KR1019900019029A KR900019029A KR910009714A KR 910009714 A KR910009714 A KR 910009714A KR 1019900019029 A KR1019900019029 A KR 1019900019029A KR 900019029 A KR900019029 A KR 900019029A KR 910009714 A KR910009714 A KR 910009714A
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- alkyl
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- thiazole
- phenylimidazo
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- 230000003308 immunostimulating effect Effects 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 239000002253 acid Substances 0.000 claims 7
- -1 nitro, amino Chemical group 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- ZKNDEKYQRZXCMG-UHFFFAOYSA-N 2-hexyl-6-phenyl-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound N1=C2SC(CCCCCC)=CN2CC1C1=CC=CC=C1 ZKNDEKYQRZXCMG-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 2
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- ZKNDEKYQRZXCMG-INIZCTEOSA-N (6r)-2-hexyl-6-phenyl-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound C1([C@@H]2CN3C=C(SC3=N2)CCCCCC)=CC=CC=C1 ZKNDEKYQRZXCMG-INIZCTEOSA-N 0.000 claims 1
- ZKNDEKYQRZXCMG-MRXNPFEDSA-N (6s)-2-hexyl-6-phenyl-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound C1([C@H]2CN3C=C(SC3=N2)CCCCCC)=CC=CC=C1 ZKNDEKYQRZXCMG-MRXNPFEDSA-N 0.000 claims 1
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 1
- NPWYNBJRNACMBL-UHFFFAOYSA-N 2-heptyl-6-phenyl-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound N1=C2SC(CCCCCCC)=CN2CC1C1=CC=CC=C1 NPWYNBJRNACMBL-UHFFFAOYSA-N 0.000 claims 1
- AQHVDPDDZRVMPC-UHFFFAOYSA-N 2-octyl-6-phenyl-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound N1=C2SC(CCCCCCCC)=CN2CC1C1=CC=CC=C1 AQHVDPDDZRVMPC-UHFFFAOYSA-N 0.000 claims 1
- GZRXNWZDDMUGDW-UHFFFAOYSA-N 2-pentyl-6-phenyl-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound N1=C2SC(CCCCC)=CN2CC1C1=CC=CC=C1 GZRXNWZDDMUGDW-UHFFFAOYSA-N 0.000 claims 1
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical group FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 claims 1
- QIKYINBTOKECCU-UHFFFAOYSA-N 6-(4-bromophenyl)-2-hexyl-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound N1=C2SC(CCCCCC)=CN2CC1C1=CC=C(Br)C=C1 QIKYINBTOKECCU-UHFFFAOYSA-N 0.000 claims 1
- 230000005526 G1 to G0 transition Effects 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 239000012190 activator Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims 1
- 150000002462 imidazolines Chemical class 0.000 claims 1
- 210000000987 immune system Anatomy 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (11)
- 하기 일반식(Ⅰ)을 갖는 화합물, 약학적으로 허용되는 이의 산부가염 또는 입체 화학적 이성체.상기식에서, Ar는 할로, 하이드록시, C1-6알킬옥시, 머캅토, C1-6알킬티오, C1-6알킬, 니트로, 아미노, 모노(C1-6알킬)아미노, 디(C1-6알킬)아미노, C1-6알킬카보닐아미노, 아릴카보닐아미노, C1-6알킬술포닐아미노, 트리플루오로메틸, 시아노, 아미노카보닐, 모노(C1-6알킬) 아미노카보닐, 디(C1-6알킬)아미노카보닐, 하이드록시카보닐, C1-6알킬옥시, 카복스알데히드 및 하이드록시메틸중에서 각각 독립적으로 선택된 1내지 3개의 치환기로 임의 치환된 페닐; 피리디닐; 티에닐; 푸라닐 또는 C1-6알킬이나 할로로 치환된 푸라닐이고; R1및 R2는 각각 독립적으로 C1-20알킬, (C3-7시클로알킬)C1-6알킬, C3-7시클로알킬, 아릴 또는 (아릴) C1-6알킬이고; R1및 R2중 하나가 수소일 수도 있고; 또는 R1및 R2가 함께 C3-6알칸디일 라디칼을 형성할 수도 있으며; 각각의 아릴은 할로, 하이드록시, C1-6알킬옥시, C1-6알킬, 니트로, 아미노, 트리플루오로메틸 또는 시아노중에서 각각 독립적으로 선택된 1내지 3개의 치환기로 임의 치환된 페닐이다.
- 제1항에 있어서, R2가 수소인 화합물.
- 제2항에 있어서, Ar이 할로, 니트로, 하이드록시,C1-6알킬-옥시, C1-6알킬, C1-6알킬카보닐아미노 및 아릴카보닐아미노 중에서 독립적으로 선택된 1내지 2개의 치환기로 임의 치환된 페닐; 티에닐; 푸라닐 또는 피리디닐인 화합물.
- 제3항에 있어서, R1이 C4-10알킬이고 Ar이 하나의 할로, 니트로, 메톡시 또는 메틸로 임의 치환된 페닐인 화합물.
- 제4항에 있어서, 6-(4-브로모페닐)-2-헥실-5,6-디하이드로이미다조[2,1-b]티아졸; 6-(4-브로모페닐)-2-펜닐-5,6-디하이드로이미다조[2,1-b]티아졸; 5,6-디하이드로-2-펜틸-6-페닐이미다조[2,1-b]티아졸; 2-헥실-5,6-디하이드로-6-페닐이미다조[2,1-b]티아졸; 2-헵틸-5,6-디하이드로-6-페닐이미다조[2,1-b]티아졸; 및 5,6-디하이드로-2-옥틸-6-페닐이미다조[2,1-b]티아졸, 약학적으로 허용되는 이들의 산부가염 또는 이들의 입체화학적 이성체.
- 제5항에 있어서, 2-헥실-5,6-디하이드로-6-페닐이미다조[2,1-b]티아졸; (S)-(-)-2-헥실-5,6-디하이드로-6-페닐이미다조[2,1-b]티아졸; (R)-(+)-2-헥실-5,6-디하이드로-6-페닐이미다조[2,1-b]티아졸; 상기 에난티오머 형태의 혼합물 또는 약학적으로 허용되는 이들의 산부가염.
- 하기 일반식(Ⅱ)을 갖는 화합물, 약학적으로 허용되는 이의 산부가염 또는 이의 입체 화학적 이성체.상기식에서, Ar, R1및 R2는 제1항에서 정의한 바와 같다.
- 하기 일반식(Ⅷ)을 갖는 화합물, 약학적으로 허용되는 이의 산부가염 또는 이의 입체 화학적 이성체.상기식에서, Ar, R1및 R2는 제1항에서 정의한 바와 같다.
- 활용 성분으로서 면역자극 유효량의 제1내지 6항중 어느 한 항에 따른 일반식(I)의 화합물과 불활성 담체를 포함하는 면역자극 조성물.
- 면역자극 유효량의 제1내지 6항에 따른 일반식(I)의 화합물을 면역계가 약화되는 질병 또는 질환일 앓고 있는 사람 및 온혈동물에게 전신 투여함을 특징로 하여 사람 및 온혈동물을 치료하는 방법.
- 활성화제의 존재하에, 임의로 반응-불활성 용매중에서 하기 일반식(Ⅱ)의 중간체를 환화시키거나; 반응-불활성 용매중에서, 임의로 염기의 존재하에 일반식 R1-CH(W1)-C=(O)-R2(V)의 시약을 사용하여 하기 일반식(Ⅳ)의 이미다졸린을 환화시키거나; 일반식(Ⅳ)의 이미다졸린을 하기 일반식(Ⅶ)의 아세탈과 반응시킨 후 이렇게 수득된 일반식(Ⅵ)의 중간체를 적합한 산으로 처리함으로써 환화시키거나; 키랄 고정상을 통해 라세미 혼합물의 용액을 용리시킴으로써 일반식(I) 화합물의 에난티오머 형태를 분리하고; 경우에 따라, 약학적으로 허용되는 산으로 처리함으로써 일반식(I)의 화합물을 염 형태로 전환시키거나; 또는 역으로, 알칼리로 처리함으로써 염 형태를 유리염기로 전환시키고; 및/또는 이의 입체 화학적 이성체를 제조함을 특징으로 하여, 제1 내지 6항중 어느 한 항에 따른 일반식(I)의 화합물을 제조하는 방법.상기식에서, Ar, R1및 R2는 일반식(I)에서 정의한 바와 같고, W1은 반응성 이탈그룹이고, R은 메틸 또는 에틸이거나 두 R그룹이 함께 에탄디일 또는 프로판디일라디칼을 형성한다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44084289A | 1989-11-24 | 1989-11-24 | |
| US440,842 | 1989-11-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR910009714A true KR910009714A (ko) | 1991-06-28 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019900019029A KR910009714A (ko) | 1989-11-24 | 1990-11-23 | 면역자극성 6-아릴-5,6-디하이드로이미다조[2,1-b]티아졸 유도체 |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP0430334B1 (ko) |
| JP (1) | JPH03170487A (ko) |
| KR (1) | KR910009714A (ko) |
| CN (1) | CN1032754C (ko) |
| AT (1) | ATE127795T1 (ko) |
| AU (1) | AU630766B2 (ko) |
| BG (1) | BG60587B1 (ko) |
| CA (1) | CA2028756A1 (ko) |
| CZ (1) | CZ281422B6 (ko) |
| DE (1) | DE69022370T2 (ko) |
| FI (1) | FI93459C (ko) |
| HU (1) | HU206361B (ko) |
| IE (1) | IE67656B1 (ko) |
| IL (1) | IL96435A (ko) |
| MY (1) | MY131024A (ko) |
| NO (1) | NO300065B1 (ko) |
| NZ (1) | NZ236026A (ko) |
| PL (1) | PL165413B1 (ko) |
| PT (1) | PT95978B (ko) |
| RO (1) | RO108869B1 (ko) |
| RU (1) | RU2051153C1 (ko) |
| YU (1) | YU47955B (ko) |
| ZA (1) | ZA909445B (ko) |
| ZM (1) | ZM5390A1 (ko) |
| ZW (1) | ZW17890A1 (ko) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0524055A1 (fr) * | 1991-07-19 | 1993-01-20 | Synthelabo | Dérivés d'imidazo[2,1-b]benzothiazole-3-acétamide, leur préparation et leur application en thérapeutique |
| US6165253A (en) * | 1994-05-23 | 2000-12-26 | New Jersey Institute Of Technology | Apparatus for removal of volatile organic compounds from gaseous mixtures |
| EP1797880A3 (en) * | 1999-01-29 | 2010-04-28 | Board Of Trustees Of The University Of Illinois | P53 inhibitors and their use for the treatment of cancer, hyperthermia, hypoxia, a burn, trauma to the central nervous system, a seizure, acute inflammation, tissue ageing, preservation of organs for transplant and preparation of a host for bone marrow transplant |
| DE60037394T2 (de) | 1999-01-29 | 2009-01-02 | The Board Of Trustees For The University Of Illinois, Urbana | VERWENDUNG VON p53 INHIBITOREN ZUR BEHANDLUNG VON NEBENERSCHEINUNGEN BEI DER KREBSTHERAPIE |
| CA2580126C (en) | 2004-09-28 | 2014-08-26 | Quark Biotech, Inc. | Oligoribonucleotides and methods of use thereof for treatment of alopecia, acute renal failure and other diseases |
| US7825099B2 (en) | 2006-01-20 | 2010-11-02 | Quark Pharmaceuticals, Inc. | Treatment or prevention of oto-pathologies by inhibition of pro-apoptotic genes |
| US7910566B2 (en) | 2006-03-09 | 2011-03-22 | Quark Pharmaceuticals Inc. | Prevention and treatment of acute renal failure and other kidney diseases by inhibition of p53 by siRNA |
| ES2474176T3 (es) | 2007-06-27 | 2014-07-08 | Quark Pharmaceuticals, Inc. | Composiciones y métodos para inhibir la expresión de genes pro-apopt�ticos |
| CN104557979A (zh) * | 2013-10-23 | 2015-04-29 | 丹阳恒安化学科技研究所有限公司 | 盐酸左旋咪唑的制备方法 |
| RU2763739C1 (ru) * | 2021-06-28 | 2021-12-30 | Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" (ПГНИУ) | (Z)-9-ароил-8-гидрокси-6-(2-гидроксифенил)-2-(((Z)-2-оксоиндолин-3-илиден)гидразоно)-1-тиа-3,6-диазаспиро[4.4]нон-8-ен-4,7-дионы, обладающие противомикробной активностью |
| WO2023093700A1 (zh) * | 2021-11-29 | 2023-06-01 | 中国海洋大学 | 咪唑并噻唑衍生物及其制备方法与应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU409983B2 (en) * | 1965-07-19 | 1970-12-31 | Imperial Chemical Industries Of Australia New Zealand Limited | Process for the manufacture of thia zolidines and thiazolidines produced thereby |
| GB1444743A (en) * | 1973-09-20 | 1976-08-04 | Pfizer Ltd | 7-substituted imidazo-1,1-b-thiazolium and 9-substituted thiazolo-3,2-a-benzimidazolium derivatives having hypogly caemic and/or growth promotant properties |
| US4340738A (en) * | 1979-06-21 | 1982-07-20 | Janssen Pharmaceutica, N.V. | 2,3-Dihydro-imidazo[2,1-b]benzothiazoles |
-
1990
- 1990-10-29 CA CA002028756A patent/CA2028756A1/en not_active Abandoned
- 1990-11-09 NZ NZ236026A patent/NZ236026A/xx unknown
- 1990-11-15 AT AT90203031T patent/ATE127795T1/de active
- 1990-11-15 DE DE69022370T patent/DE69022370T2/de not_active Expired - Fee Related
- 1990-11-15 EP EP90203031A patent/EP0430334B1/en not_active Expired - Lifetime
- 1990-11-17 JP JP2310193A patent/JPH03170487A/ja active Pending
- 1990-11-20 YU YU220890A patent/YU47955B/sh unknown
- 1990-11-21 AU AU66809/90A patent/AU630766B2/en not_active Ceased
- 1990-11-21 MY MYPI90002052A patent/MY131024A/en unknown
- 1990-11-22 BG BG93298A patent/BG60587B1/bg unknown
- 1990-11-22 CZ CS905803A patent/CZ281422B6/cs unknown
- 1990-11-22 IL IL9643590A patent/IL96435A/en not_active IP Right Cessation
- 1990-11-23 HU HU907633A patent/HU206361B/hu not_active IP Right Cessation
- 1990-11-23 KR KR1019900019029A patent/KR910009714A/ko not_active Application Discontinuation
- 1990-11-23 PT PT95978A patent/PT95978B/pt not_active IP Right Cessation
- 1990-11-23 ZW ZW178/90A patent/ZW17890A1/xx unknown
- 1990-11-23 PL PL90287907A patent/PL165413B1/pl unknown
- 1990-11-23 IE IE424190A patent/IE67656B1/en not_active IP Right Cessation
- 1990-11-23 ZM ZM53/90A patent/ZM5390A1/xx unknown
- 1990-11-23 ZA ZA909445A patent/ZA909445B/xx unknown
- 1990-11-23 FI FI905788A patent/FI93459C/fi not_active IP Right Cessation
- 1990-11-23 RO RO146390A patent/RO108869B1/ro unknown
- 1990-11-23 RU SU904831684A patent/RU2051153C1/ru active
- 1990-11-23 NO NO905086A patent/NO300065B1/no unknown
- 1990-11-24 CN CN90109407A patent/CN1032754C/zh not_active Expired - Fee Related
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