KR910700073A - 마크로사이클릭 아미노포스폰산 착화합물, 그의 제조방법, 이를 포함하는 배합물 및 용도 - Google Patents
마크로사이클릭 아미노포스폰산 착화합물, 그의 제조방법, 이를 포함하는 배합물 및 용도Info
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- KR910700073A KR910700073A KR1019900701800A KR900701800A KR910700073A KR 910700073 A KR910700073 A KR 910700073A KR 1019900701800 A KR1019900701800 A KR 1019900701800A KR 900701800 A KR900701800 A KR 900701800A KR 910700073 A KR910700073 A KR 910700073A
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- Prior art keywords
- composition
- physiologically acceptable
- radionuclide
- animal
- reacting
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- 238000000034 method Methods 0.000 title claims 10
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical class NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 title claims 4
- 239000000203 mixture Substances 0.000 claims 30
- 150000003839 salts Chemical class 0.000 claims 10
- RCXMQNIDOFXYDO-UHFFFAOYSA-N [4,7,10-tris(phosphonomethyl)-1,4,7,10-tetrazacyclododec-1-yl]methylphosphonic acid Chemical compound OP(O)(=O)CN1CCN(CP(O)(O)=O)CCN(CP(O)(O)=O)CCN(CP(O)(O)=O)CC1 RCXMQNIDOFXYDO-UHFFFAOYSA-N 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 239000003446 ligand Substances 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 2
- 230000037396 body weight Effects 0.000 claims 2
- 239000002552 dosage form Substances 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 239000011574 phosphorus Substances 0.000 claims 2
- 230000002285 radioactive effect Effects 0.000 claims 2
- QBPPRVHXOZRESW-UHFFFAOYSA-N 1,4,7,10-tetraazacyclododecane Chemical compound C1CNCCNCCNCCN1 QBPPRVHXOZRESW-UHFFFAOYSA-N 0.000 claims 1
- 206010006002 Bone pain Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- -1 phosphone Chemical class 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0474—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group
- A61K51/0482—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group chelates from cyclic ligands, e.g. DOTA
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0489—Phosphates or phosphonates, e.g. bone-seeking phosphonates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3817—Acids containing the structure (RX)2P(=X)-alk-N...P (X = O, S, Se)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2121/00—Preparations for use in therapy
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/06—Chelate
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (27)
- (1)마크로사이클릭 부분으로서 1, 4, 7, 10-테트라아자사이클로 도데칸을 함유하는 마크로사이클릭 아미노포스폰산 또는 그의 생리학적으로 허용가능한 염(여기에서 질소와 인은 하기 일반식 (Ⅰ)의 알킬렌 또는 치환된 알킬렌 라디칼에 의해 상호연결된다)과 (2)Sm-153, Gd-159, Ho-166, Lu-177, Y-90 또는 Yb-175중 적어도 하나의 방사성 핵종을 갖는 착화합물을 포함하는, 치료에 효과적인 조성물.상기식에서, X 및 Y는 독립적으로 수소, 하이드록실, 카복실, 포스폰, 또는 1개 내지 8개의 탄소원자를 갖는 탄화수소 라디칼 및 상기 산 라디칼의 생리학적으로 허용가능한 염이고, n은 1 내지 3이며, 단 n＞1일 때 X 및 Y는 각각 어떤 다른 탄소원자의 X 및 Y와 동일하거나 또는 다를 수 있다.
- 제1항에 있어서, X 및 Y 가 수소이고 n이 1인 조성물.
- 제1항에 있어서, 상기 마크로사이클릭 아미노포스폰산이 하기 구조(Ⅱ)을 갖는 조성물.상기식에서, 치환체 A, B, C 및 D는 독립적으로 수소, 1개 내지 8개의 탄소원자를 갖는 탄화수소 라디칼 또는 하기 일반식의 잔기 및 상기 산 라디칼의 생리학적으로 허용가능한 염이다.〔상기식에서, X, Y 및 n은 제1항에서 정의한 바와같고, X′ 및 Y′는 독립적으로 수소, 메틸 또는 에틸 라디칼이며, n′ 는 2또는 3이나, 단 상기 질소 치환체 중 적어도 2개는 인-함유 그룹이다〕.
- 제3항에 있어서, 상기 마이크사이클릭 아미노포스폰산이 1, 4, 7, 10-테트라아자 사이클로도데칸-1, 4, 7, 10-테트라메틸렌 포스폰산 또는 그의 생리학적으로 허용가능한 염인 조성물.
- 제1항 내지 4항중 어느 한 항에 있어서, 상기 방사성 핵종이 Gd-159인 조성물.
- 제1, 2, 3 또는 4항에 있어서, 상기 방사성 핵종이 Sm-153인 조성물.
- 제1, 2, 3 또는 4항에 있어서, 상기 방사성 핵종이 Lu-177인 조성물.
- 제1, 2, 3 또는 4항에 있어서, 상기 방사성 핵종이 Yb-175인 조성물.
- 제1, 2, 3 또는 4항에 있어서, 상기 방사성 핵종이 Ho-166인 조성물.
- 제1, 2, 3 또는 4항에 있어서, 상기 방사성 핵종이 Y-90인 조성물.
- 제1항 내지 10항중 어느 한 항에 청구된 착화합물을 함유하고, 투여형태내의 방사성 핵종의 동물의 체중㎏당 적어도 0.02mCi를 함유하는 양으로 존재하는, 동물에게 투여하는데 적합한 멸균 조성물.
- 제11항에 있어서, 투여형태내의 상기 방사성 핵종이 상기 동물의 체중 ㎏당 적어도 0.2mCi를 함유하는 양으로 존재하는 조성물.
- 제1항 내지 12항중 어느 한 항에 있어서, 리간드 대 방사성 핵종의 몰비가 적어도 약 1 : 1 내지 3 : 1이 조성물.
- 제13항에 있어서, 리간드 대 방사성 몰비가 1 : 1 내지 3 : 1인 조성물.
- 제13항에 있어서, 리간드 대 방사성 몰비가 1 : 1 내지 1.5 : 1인 조성물.
- 제1항 내지 15항중 어느 한 항에 청구된 조성물 및 약학적으로 허용가능한 담체를 포함하는 약학적 배합물.
- 제16항에 있어서, 착화합물 및 존재하는 완충제를 갖는 배합물을 키트 형태로 동결시키고, 상기 동결된 배합물을 사용하기 전에 나중에 해동시키는 약학적 조성물.
- 제16 또는 17항에 청구된 적어도 하나의 약학적 배합물 또는 제1항 내지 15항에 청구된 적어도 하나의 조성물의 치료학적으로 효과적인 양을 하나이상의 석회형성성 종양을 갖는 동물에게 투여함을 포함하는 상기 동물의 치료방법.
- 제16 또는 17항에 청구된 적어도 하나의 약학적 배합물 또는 제1항 내지 15항에 청구된 적어도 하나의 조성물의 치료학적으로 효과적인 양을 골 통증을 갖는 동물에게 투여함을 포함하는 상기 동물의 치료방법.
- 제18 또는 19항에 있어서, 상기 동물이 인간인 방법.
- 조정된 pH의 수중에서 Sm-153, Gd-159, Ho-166, Lu-177, Y-90 또는 Yb-175의 방사성 핵종을 제1항 내지 20항중 어느 한 항에 청구된 마이크사이클릭 아미노포스폰산과 반응시킴을 포함하는 제1항에 청구된 조성물의 제조방법.
- 제21항에 있어서, 조성된 pH의 수중에서 1, 4, 7, 10-테트라아자 사이클로도데칸-1, 4, 7, 10-테트라메틸렌 포스폰산 또는 그의 생리학적으로 허용가능한 염을 Sm-153과 반응시킴을 포함하는 조성물의 제조방법.
- 제21항에 있어서, 조성된 pH의 수중에서 1, 4, 7, 10-테트라아자 사이클로도데칸-1, 4, 7, 10-테트라메틸렌 포스폰산 또는 그의 생리학적으로 허용가능한 염을 Gd-159과 반응시킴을 포함하는 조성물의 제조방법.
- 제21항에 있어서, 조성된 pH의 수중에서 1, 4, 7, 10-테트라아자 사이클로도데칸-1, 4, 7, 10-테트라메틸렌 포스폰산 또는 그의 생리학적으로 허용가능한 염을 Ho-166과 반응시킴을 포함하는 조성물의 제조방법.
- 제21항에 있어서, 조성된 pH의 수중에서 1, 4, 7, 10-테트라아자 사이클로도데칸-1, 4, 7, 10-테트라메틸렌 포스폰산 또는 그의 생리학적으로 허용가능한 염을 Lu-177과 반응시킴을 포함하는 조성물의 제조방법.
- 제21항에 있어서, 조성된 pH의 수중에서 1, 4, 7, 10-테트라아자 사이클로도데칸-1, 4, 7, 10-테트라메틸렌 포스폰산 또는 그의 생리학적으로 허용가능한 염을 Y-90과 반응시킴을 포함하는 조성물의 제조방법.
- 제21항에 있어서, 조성된 pH의 수중에서 1, 4, 7, 10-테트라아자 사이클로도데칸-1, 4, 7, 10-테트라메틸렌 포스폰산 또는 그의 생리학적으로 허용가능한 염을 Yb-175과 반응시킴을 포함하는 조성물의 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/284,876 US5059412A (en) | 1984-06-04 | 1988-12-19 | Macrocyclic aminophosphonic acid complexes for the treatment of calcific tumors |
| US284,876 | 1988-12-19 | ||
| PCT/US1989/005782 WO1990006776A1 (en) | 1988-12-19 | 1989-12-15 | Macrocyclic aminophosphonic acid complexes, their preparation, formulations and use |
| US284876 | 1994-08-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR910700073A true KR910700073A (ko) | 1991-03-13 |
| KR0178966B1 KR0178966B1 (ko) | 1999-03-20 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019900701800A KR0178966B1 (ko) | 1988-12-19 | 1989-12-15 | 마크로사이클릭 아미노포스폰산 착화합물, 그의 제조방법, 이를 포함하는 배합물 및 용도 |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US5059412A (ko) |
| EP (2) | EP0408701B1 (ko) |
| JP (1) | JP2515929B2 (ko) |
| KR (1) | KR0178966B1 (ko) |
| CN (1) | CN1025983C (ko) |
| AR (1) | AR248140A1 (ko) |
| AT (1) | ATE112689T1 (ko) |
| AU (3) | AU639899B2 (ko) |
| BR (1) | BR8907255A (ko) |
| CA (1) | CA2005880C (ko) |
| CY (1) | CY1902A (ko) |
| DE (1) | DE68918852T2 (ko) |
| DK (1) | DK175479B1 (ko) |
| ES (1) | ES2061010T3 (ko) |
| FI (1) | FI101857B1 (ko) |
| HK (1) | HK146795A (ko) |
| HU (1) | HU207454B (ko) |
| IE (2) | IE940833L (ko) |
| IL (1) | IL92784A (ko) |
| MX (1) | MX18786A (ko) |
| NO (1) | NO180434C (ko) |
| NZ (1) | NZ231818A (ko) |
| PT (1) | PT92619B (ko) |
| SA (1) | SA91120234B1 (ko) |
| WO (1) | WO1990006776A1 (ko) |
| ZA (1) | ZA899734B (ko) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5059412A (en) * | 1984-06-04 | 1991-10-22 | The Dow Chemical Company | Macrocyclic aminophosphonic acid complexes for the treatment of calcific tumors |
| US5645818A (en) * | 1989-03-24 | 1997-07-08 | Guerbet S.A. | Diagnostic compositions comprising a complex formed by a nitrogenous macrocyclic ligand with metal ions |
| DE4009119A1 (de) * | 1990-03-19 | 1991-09-26 | Schering Ag | 1,4,7,10-tetraazacyclododecan-butyltriole, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
| WO1991016075A1 (en) * | 1990-04-20 | 1991-10-31 | Australian Nuclear Science & Technology Organisation | Bone marrow treatments |
| PT98000B (pt) * | 1990-06-18 | 1998-11-30 | Dow Chemical Co | Metodo de utilizacao de complexos de acido aminofosfonico como agentes produtores de imagens |
| MC2260A1 (fr) * | 1990-06-18 | 1993-04-26 | Dow Chemical Co | Formulations de produits radiopharmaceutiques,leur methode d'administration et leur procede de preparation |
| DE4035760A1 (de) * | 1990-11-08 | 1992-05-14 | Schering Ag | Mono-n-substituierte 1,4,7,10-tetraazacyclododecan-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
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| US3965254A (en) * | 1973-05-23 | 1976-06-22 | The Procter & Gamble Company | Compositions for the treatment of calcific tumors |
| US4017595A (en) * | 1975-08-28 | 1977-04-12 | Research Corporation | Bone-seeking indium-113m or indium-111 organic phosphonate complexes |
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| US4957939A (en) * | 1981-07-24 | 1990-09-18 | Schering Aktiengesellschaft | Sterile pharmaceutical compositions of gadolinium chelates useful enhancing NMR imaging |
| SU1098937A1 (ru) * | 1983-03-25 | 1984-06-23 | Ордена Ленина институт элементоорганических соединений им.А.Н.Несмеянова | 1,4,7,10-Тетра/диоксифосфорилметил/-1,4,7,10-тетраазациклододекан в качестве комплексона дл св зывани катионов меди /п/,кобальта /п/,кадми /п/,свинца /п/ и лантана /ш/ |
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| US4882142A (en) * | 1988-12-19 | 1989-11-21 | The Dow Chemical Company | Bone marrow suppressing agents |
-
1988
- 1988-12-19 US US07/284,876 patent/US5059412A/en not_active Expired - Lifetime
-
1989
- 1989-12-15 CY CY190289A patent/CY1902A/xx unknown
- 1989-12-15 HU HU901163A patent/HU207454B/hu not_active IP Right Cessation
- 1989-12-15 BR BR898907255A patent/BR8907255A/pt not_active Application Discontinuation
- 1989-12-15 DE DE68918852T patent/DE68918852T2/de not_active Expired - Lifetime
- 1989-12-15 EP EP90901464A patent/EP0408701B1/en not_active Expired - Lifetime
- 1989-12-15 KR KR1019900701800A patent/KR0178966B1/ko not_active IP Right Cessation
- 1989-12-15 JP JP2501907A patent/JP2515929B2/ja not_active Expired - Fee Related
- 1989-12-15 WO PCT/US1989/005782 patent/WO1990006776A1/en active IP Right Grant
- 1989-12-15 AU AU48282/90A patent/AU639899B2/en not_active Expired
- 1989-12-15 AT AT90901464T patent/ATE112689T1/de not_active IP Right Cessation
- 1989-12-15 ES ES90901464T patent/ES2061010T3/es not_active Expired - Lifetime
- 1989-12-18 CA CA002005880A patent/CA2005880C/en not_active Expired - Lifetime
- 1989-12-18 IE IE940833A patent/IE940833L/xx unknown
- 1989-12-18 IL IL9278489A patent/IL92784A/en unknown
- 1989-12-18 IE IE406389A patent/IE66391B1/en not_active IP Right Cessation
- 1989-12-18 NZ NZ231818A patent/NZ231818A/en unknown
- 1989-12-19 AR AR89315722A patent/AR248140A1/es active
- 1989-12-19 AU AU47009/89A patent/AU4700989A/en not_active Abandoned
- 1989-12-19 MX MX1878689A patent/MX18786A/es unknown
- 1989-12-19 ZA ZA899734A patent/ZA899734B/xx unknown
- 1989-12-19 PT PT92619A patent/PT92619B/pt not_active IP Right Cessation
- 1989-12-19 EP EP19890313308 patent/EP0375376A3/en not_active Withdrawn
- 1989-12-19 CN CN89109819A patent/CN1025983C/zh not_active Expired - Lifetime
-
1990
- 1990-08-16 DK DK199001959A patent/DK175479B1/da not_active IP Right Cessation
- 1990-08-17 FI FI904084A patent/FI101857B1/fi not_active IP Right Cessation
- 1990-08-17 NO NO903632A patent/NO180434C/no not_active IP Right Cessation
-
1991
- 1991-11-20 SA SA91120234A patent/SA91120234B1/ar unknown
-
1993
- 1993-11-12 AU AU50685/93A patent/AU657641B2/en not_active Expired
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1995
- 1995-09-14 HK HK146795A patent/HK146795A/xx not_active IP Right Cessation
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