CA1057748A - Piperazinylimino rifamycins - Google Patents
Piperazinylimino rifamycinsInfo
- Publication number
- CA1057748A CA1057748A CA247,156A CA247156A CA1057748A CA 1057748 A CA1057748 A CA 1057748A CA 247156 A CA247156 A CA 247156A CA 1057748 A CA1057748 A CA 1057748A
- Authority
- CA
- Canada
- Prior art keywords
- rifamycin
- piperazinyl
- iminomethyl
- methyl
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 Piperazinylimino rifamycins Chemical class 0.000 title claims description 17
- 229930189077 Rifamycin Natural products 0.000 title claims description 12
- 229940081192 rifamycins Drugs 0.000 title description 7
- IYPZRUYMFDWKSS-UHFFFAOYSA-N piperazin-1-amine Chemical compound NN1CCNCC1 IYPZRUYMFDWKSS-UHFFFAOYSA-N 0.000 claims abstract description 10
- BBNQHOMJRFAQBN-UPZFVJMDSA-N 3-formylrifamycin sv Chemical compound OC1=C(C(O)=C2C)C3=C(O)C(C=O)=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O BBNQHOMJRFAQBN-UPZFVJMDSA-N 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 229960003292 rifamycin Drugs 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 4
- YVMFFWRWROZJTP-KEGRAMFISA-N [(9E,19E,21E)-26-[(E)-(4-cyclobutylpiperazin-1-yl)iminomethyl]-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate Chemical group COC1\C=C\OC2(C)Oc3c(C2=O)c2c(O)c(\C=N\N4CCN(CC4)C4CCC4)c(NC(=O)\C(C)=C\C=C\C(C)C(O)C(C)C(O)C(C)C(OC(C)=O)C1C)c(O)c2c(O)c3C YVMFFWRWROZJTP-KEGRAMFISA-N 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- WDZCUPBHRAEYDL-GZAUEHORSA-N rifapentine Chemical group O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C(O)=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N(CC1)CCN1C1CCCC1 WDZCUPBHRAEYDL-GZAUEHORSA-N 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000532 dioxanyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 10
- HJYYPODYNSCCOU-ODRIEIDWSA-N rifamycin SV Chemical class OC1=C(C(O)=C2C)C3=C(O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O HJYYPODYNSCCOU-ODRIEIDWSA-N 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 208000015181 infectious disease Diseases 0.000 abstract description 3
- 231100000053 low toxicity Toxicity 0.000 abstract description 3
- 230000003442 weekly effect Effects 0.000 abstract description 2
- 229940109171 rifamycin sv Drugs 0.000 description 10
- HJYYPODYNSCCOU-ZDHWWVNNSA-N Rifamycin SV Natural products COC1C=COC2(C)Oc3c(C)c(O)c4c(O)c(NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C)cc(O)c4c3C2=O HJYYPODYNSCCOU-ZDHWWVNNSA-N 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 6
- JQXXHWHPUNPDRT-ZNQWNCHJSA-N [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(4-methylpiperazin-1-yl)iminomethyl]-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)Nc2c(O)c3c(O)c4C)C)OC)c4c1c3c(O)c2C=NN1CCN(C)CC1 JQXXHWHPUNPDRT-ZNQWNCHJSA-N 0.000 description 6
- 229960001225 rifampicin Drugs 0.000 description 6
- BTVYFIMKUHNOBZ-QXMMDKDBSA-N rifamycin s Chemical class O=C1C(C(O)=C2C)=C3C(=O)C=C1NC(=O)\C(C)=C/C=C\C(C)C(O)C(C)C(O)C(C)C(OC(C)=O)C(C)C(OC)\C=C/OC1(C)OC2=C3C1=O BTVYFIMKUHNOBZ-QXMMDKDBSA-N 0.000 description 6
- 125000001511 cyclopentyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910010084 LiAlH4 Inorganic materials 0.000 description 2
- CVTIZMOISGMZRJ-UHFFFAOYSA-N N-Mononitrosopiperazine Chemical compound O=NN1CCNCC1 CVTIZMOISGMZRJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000001995 cyclobutyl group Chemical class [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GQGAYGXLSPDXOS-UHFFFAOYSA-N 1-cyclopropyl-4-nitrosopiperazine Chemical compound N(=O)N1CCN(CC1)C1CC1 GQGAYGXLSPDXOS-UHFFFAOYSA-N 0.000 description 1
- MMFSEQBRBIYYJY-UHFFFAOYSA-N 4-cyclobutylpiperazin-1-amine Chemical compound C1CN(N)CCN1C1CCC1 MMFSEQBRBIYYJY-UHFFFAOYSA-N 0.000 description 1
- QYHRIASMJNLWHJ-UHFFFAOYSA-N 4-cyclopentylpiperazin-1-amine Chemical compound C1CN(N)CCN1C1CCCC1 QYHRIASMJNLWHJ-UHFFFAOYSA-N 0.000 description 1
- RJWLLQWLBMJCFD-UHFFFAOYSA-N 4-methylpiperazin-1-amine Chemical compound CN1CCN(N)CC1 RJWLLQWLBMJCFD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 206010024229 Leprosy Diseases 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
- 241001646725 Mycobacterium tuberculosis H37Rv Species 0.000 description 1
- 108700035964 Mycobacterium tuberculosis HsaD Proteins 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- HHRFWSALGNYPHA-UHFFFAOYSA-N [N].C1CNCCN1 Chemical compound [N].C1CNCCN1 HHRFWSALGNYPHA-UHFFFAOYSA-N 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 229940088623 biologically active substance Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BRTFVKHPEHKBQF-UHFFFAOYSA-N bromocyclopentane Chemical compound BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000009935 nitrosation Effects 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/08—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB10020/75A GB1478563A (en) | 1975-03-05 | 1975-03-05 | Rifamycin derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1057748A true CA1057748A (en) | 1979-07-03 |
Family
ID=9959968
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA247,156A Expired CA1057748A (en) | 1975-03-05 | 1976-03-04 | Piperazinylimino rifamycins |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4002752A (en:Method) |
| JP (1) | JPS51113900A (en:Method) |
| AR (1) | AR210113A1 (en:Method) |
| AT (1) | AT344896B (en:Method) |
| BE (1) | BE839255A (en:Method) |
| CA (1) | CA1057748A (en:Method) |
| CH (1) | CH610325A5 (en:Method) |
| DD (1) | DD123888A5 (en:Method) |
| DE (1) | DE2608218C3 (en:Method) |
| DK (1) | DK136655B (en:Method) |
| ES (1) | ES445790A1 (en:Method) |
| FI (1) | FI59102C (en:Method) |
| FR (1) | FR2302742A1 (en:Method) |
| GB (1) | GB1478563A (en:Method) |
| HK (1) | HK35282A (en:Method) |
| HU (1) | HU170451B (en:Method) |
| IE (1) | IE42881B1 (en:Method) |
| KE (1) | KE3099A (en:Method) |
| LU (1) | LU74478A1 (en:Method) |
| MX (1) | MX3737E (en:Method) |
| NL (1) | NL165745C (en:Method) |
| NO (1) | NO143796C (en:Method) |
| PT (1) | PT64866B (en:Method) |
| SE (1) | SE420728B (en:Method) |
| SU (1) | SU575030A3 (en:Method) |
| YU (1) | YU39477B (en:Method) |
| ZA (1) | ZA761043B (en:Method) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2728869A1 (de) * | 1976-06-25 | 1977-12-29 | Antibiotice Iasi Intreprindere | Rifamycinen und verfahren zu deren herstellung |
| GR64108B (en) * | 1977-04-15 | 1980-01-24 | Dso Pharmachim | Method for the preparation of azomethine-derivatives of rifamycin s.v |
| GB1576886A (en) * | 1977-04-20 | 1980-10-15 | Lepetit Spa | Rifamycin derivatives |
| GB1594134A (en) * | 1977-11-25 | 1981-07-30 | Holco Investment Inc | Rifamycins |
| AU536524B2 (en) * | 1979-06-28 | 1984-05-10 | Gruppo Lepetit S.P.A. | Water soluble hydrozones of 3-formylifamyan |
| US4447432A (en) * | 1981-11-17 | 1984-05-08 | Farmitalia Carlo Erba S.P.A. | Azino rifamycins |
| US4681938A (en) * | 1984-08-27 | 1987-07-21 | Ciba-Geigy Corporation | Novel polycyclic hydrazones of rifamycins, their manufacture, and their pharmaceutical compositions for treating tuberculosis |
| ATE47857T1 (de) * | 1985-10-18 | 1989-11-15 | Ciba Geigy Ag | Substituierte 4-benzyl-piperazinyl-verbindungen. |
| JPH02501301A (ja) * | 1987-09-25 | 1990-05-10 | チバ‐ガイギー アクチェンゲゼルシャフト | ４‐（トリアルキルベンジル）‐ピペラジニル化合物のジアシル誘導体 |
| GB8816620D0 (en) * | 1988-07-13 | 1988-08-17 | Lepetit Spa | Rifapentine hydrohalides |
| CA2082809C (en) * | 1990-06-29 | 1995-10-17 | Marino Nebuloni | Pure crystalline form of rifapentine |
| KR101327635B1 (ko) | 2005-08-11 | 2013-11-12 | 타간타 테라퓨틱스 인크. | 포스폰산화 리파마이신, 및 그의 뼈 및 관절 감염의 저지및 치료 용도 |
| EP2324041A4 (en) | 2008-08-13 | 2012-06-13 | Targanta Therapeutics Corp | PHOSPHONIZED RIFAMYCINS AND ITS APPLICATION FOR THE PREVENTION AND TREATMENT OF BONE AND JOINT INFECTIONS |
| RU2496475C2 (ru) | 2011-10-26 | 2013-10-27 | Александр Васильевич Иващенко | Фармацевтическая композиция и набор для лечения бактериальных инфекций |
| BR112015002945B1 (pt) | 2012-08-13 | 2021-08-31 | Adipharm Ead | Formulações farmacêuticas contendo derivados de 3-(4-cinamil-1-piperazinil)-amino de 3- formil-rifamicina sv e 3-formil-rifamicina s e um processo para sua preparação |
| CN103951677B (zh) * | 2014-03-17 | 2016-04-06 | 四川省长征药业股份有限公司 | 利福喷丁的制备方法 |
| MX2023012416A (es) * | 2021-04-21 | 2024-03-05 | Interquim S A De C V | Proceso de obtencion de rifapentina con una nueva forma cristalina. |
| CN115047122B (zh) * | 2022-06-29 | 2023-05-02 | 重庆华邦胜凯制药有限公司 | 利福喷丁及其合成过程中所产生的杂质的分析方法 |
| CN117186032A (zh) * | 2023-09-08 | 2023-12-08 | 徐州博康信息化学品有限公司 | 1-氨基-4-环戊基哌嗪及其中间体的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR208F (en:Method) * | 1964-07-31 | |||
| AR205434A1 (es) * | 1972-03-27 | 1976-05-07 | Lepetit Spa | Proceso para la preparacion de 3-acilhidrazonometil rifamicinas sv |
| GB1392272A (en) * | 1972-05-31 | 1975-04-30 | Lepetit Spa | 3-formylrifamycin azines |
-
1975
- 1975-03-05 GB GB10020/75A patent/GB1478563A/en not_active Expired
-
1976
- 1976-02-19 NO NO760549A patent/NO143796C/no unknown
- 1976-02-23 SE SE7602122A patent/SE420728B/xx not_active IP Right Cessation
- 1976-02-23 ZA ZA1043A patent/ZA761043B/xx unknown
- 1976-02-25 DK DK78476AA patent/DK136655B/da not_active IP Right Cessation
- 1976-02-26 US US05/661,587 patent/US4002752A/en not_active Expired - Lifetime
- 1976-02-28 DE DE2608218A patent/DE2608218C3/de not_active Expired
- 1976-03-03 AR AR262431A patent/AR210113A1/es active
- 1976-03-03 SU SU7602329559A patent/SU575030A3/ru active
- 1976-03-03 NL NL7602191.A patent/NL165745C/xx not_active IP Right Cessation
- 1976-03-04 HU HULE790A patent/HU170451B/hu unknown
- 1976-03-04 CA CA247,156A patent/CA1057748A/en not_active Expired
- 1976-03-04 PT PT64866A patent/PT64866B/pt unknown
- 1976-03-04 IE IE448/76A patent/IE42881B1/en not_active IP Right Cessation
- 1976-03-04 CH CH271376A patent/CH610325A5/xx not_active IP Right Cessation
- 1976-03-04 MX MX7636U patent/MX3737E/es unknown
- 1976-03-04 JP JP51023701A patent/JPS51113900A/ja active Granted
- 1976-03-04 LU LU74478A patent/LU74478A1/xx unknown
- 1976-03-05 YU YU572/76A patent/YU39477B/xx unknown
- 1976-03-05 FI FI760561A patent/FI59102C/fi not_active IP Right Cessation
- 1976-03-05 BE BE164907A patent/BE839255A/xx not_active IP Right Cessation
- 1976-03-05 AT AT162876A patent/AT344896B/de not_active IP Right Cessation
- 1976-03-05 DD DD191727A patent/DD123888A5/xx unknown
- 1976-03-05 FR FR7606379A patent/FR2302742A1/fr active Granted
- 1976-03-05 ES ES445790A patent/ES445790A1/es not_active Expired
-
1980
- 1980-11-01 KE KE3099A patent/KE3099A/xx unknown
-
1982
- 1982-08-03 HK HK352/82A patent/HK35282A/xx unknown
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