PL163730B1 - Sposób wytwarzania 1 -benzylo-3-hydroksymetylo-Indazolu PL PL PL PL PL PL PL PL - Google Patents
Sposób wytwarzania 1 -benzylo-3-hydroksymetylo-Indazolu PL PL PL PL PL PL PL PLInfo
- Publication number
- PL163730B1 PL163730B1 PL90285287A PL28528790A PL163730B1 PL 163730 B1 PL163730 B1 PL 163730B1 PL 90285287 A PL90285287 A PL 90285287A PL 28528790 A PL28528790 A PL 28528790A PL 163730 B1 PL163730 B1 PL 163730B1
- Authority
- PL
- Poland
- Prior art keywords
- toluene
- preparation
- aluminum hydride
- solvent
- indazole derivatives
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title abstract description 4
- 125000003453 indazolyl group Chemical class N1N=C(C2=C1C=CC=C2)* 0.000 title 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- -1 aliphatic ester Chemical class 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 4
- AKQDXNFPEFHRLS-UHFFFAOYSA-N (1-benzylindazol-3-yl)methanol Chemical compound C12=CC=CC=C2C(CO)=NN1CC1=CC=CC=C1 AKQDXNFPEFHRLS-UHFFFAOYSA-N 0.000 claims description 3
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- CDRCOZFGMPTGBL-UHFFFAOYSA-N 1-benzylindazole-3-carboxylic acid Chemical compound C12=CC=CC=C2C(C(=O)O)=NN1CC1=CC=CC=C1 CDRCOZFGMPTGBL-UHFFFAOYSA-N 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QLFNUXTWJGXNLH-UHFFFAOYSA-N bis(2-methoxyethoxy)alumane Chemical compound COCCO[AlH]OCCOC QLFNUXTWJGXNLH-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- VTSHLYGWBHQEGS-UHFFFAOYSA-N ethyl 1-benzylindazole-3-carboxylate Chemical compound C12=CC=CC=C2C(C(=O)OCC)=NN1CC1=CC=CC=C1 VTSHLYGWBHQEGS-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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]
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Rheumatology (AREA)
- Neurosurgery (AREA)
- Ophthalmology & Optometry (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
1 . Sposób wytwarzania 1-benzylo-3-hydroksymetylo-indazolu, znamienny tym, ze kwas 1-benzyloindazolokarboksylowy-3 lub jego ester alifatyczny, poddaje sie redu- kcji przy uzyciu srodka redukujacego, takiego jak wodorek glinowo-litowy, wodorek dwu(2-metoksyetoksy)glinowo-sodowy, korzystnie o stezeniu 70% w toluenie lub czteroizopropoksyalanian wapniowy, korzystnie o stezeniu 70% w toluenie, w obecnosci odpowiedniego rozpuszczalnika, w temperaturze od 0°C do temperatury wrzenia miesza- niny reakcyjnej, w ciagu od 30 minut do 12 godzin. PL PL PL PL PL PL PL PL
Description
Przedmiotem wynalazku jest sposób wytwarzania l-benzylo-3-hydroksymetyloindazo>lu. Związek ten i jego pochodne (np. związki zawierające zamiast grupy hydroksylowej atom chlorowca, względnie ugrupowanie alkoholanu metalu alkalicznego albo arylo- lub alkilosulfonianu) są użyteczne np. jako związki wyjściowe do wytwarzania nowych eterowych pochodnych l-benzylo-3-hydroksymetyloindazolu, mających działanie przeciwbólowe.
Sposób wytwarzania 1-benzylo-3-hydroksymetyloindazolu polega według wynalazku na tym, że kwas 1-benzyloindazolokarboksylowy-3 lub jego ester alifatyczny poddaje się redukcji przy użyciu odpowiedniego środka redukującego, takiegojak wodorek glinowo-litowy, wodorek dwu(2-metoksyetoksy)glinowo-sodowy (korzystnie o stężeniu 70% w toluenie) lub czteroizopropoksyalanian wapniowy (korzystnie o stężeniu 70% w toluenie), w obecności odpowiedniego rozpuszczalnika, w temperaturze od 0°C do temperatury wrzenia mieszaniny reakcyjnej, w ciągu od 30 minut do 12 godzin. Korzystnie jako rozpuszczalnik stosuje się eter etylowy, tetrahydrofuran, toluen lub ich mieszaniny.
Przykład. Do zawiesiny 2 g wodorku glinowo-litowego w 50 ml eteru etylowego wkrapla się w trakcie mieszania roztwór 12,5 g 1-benzyloindazolokarboksylanu-3 etylu (Von Auvers Schaich. Chem. Ber. 54, 1756, 1921) w 30 ml bezwodnego tetrahydrofuran u. Po zakończeniu wkraplania mieszaninę reakcyjną refluksuje się przez 90 minut. Po ochłodzeniu mieszaninę reakcyjną poddaje się obróbce w znany sposób i powstały osad odsącza się. Pozostałość uzyskaną po odparowaniu rozpuszczalnika poddaje się rekrystalizacji i izopropanolu. Tak otrzymuje się 1-benzlo-3-hydroksymetyloindazol o 1 1. 85-86°C.
Departament Wydawnictw UP RP Nakład 90 egz. Cena 10 000 zł
Claims (2)
- Zastrzeżenia patentowe1. Sposób wytwarzania 1-benzylo-3-hydroksymetylo-indazolu, znamienny tym, że kwas l-benzyloindazolokarboksylowy-3 lub jego ester alifatyczny, poddaje się redukcji przy użyciu środka redukującego, takiego jak wodorek glinowo-litowy, wodorek dwu(2metoksyetoksy)glinowo-sodowy, korzystnie o stężeniu 70% w toluenie lub czteroizopropoksyalanian wapniowy, korzystnie o stężeniu 70% w toluenie, w obecności odpowiedniego rozpuszczalnika, w temperaturze od 0°C do temperatury wrzenia mieszaniny reakcyjnej, w ciągu od 30 minut do 12 godzin.
- 2. Sposób według zastrz. 1, znamienny tym, że jako rozpuszczalnik stosuje się eter etylowy, tetrahydrofuran, toluen lub ich mieszaniny.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT8947620A IT1230441B (it) | 1989-02-07 | 1989-02-07 | Eteri della serie dell'indazolo |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL163730B1 true PL163730B1 (pl) | 1994-04-29 |
Family
ID=11261479
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL90285287A PL163730B1 (pl) | 1989-02-07 | 1990-02-05 | Sposób wytwarzania 1 -benzylo-3-hydroksymetylo-Indazolu PL PL PL PL PL PL PL PL |
| PL90283638A PL163720B1 (pl) | 1989-02-07 | 1990-02-05 | Sposób wytwarzania nowych eterowych pochodnych 1-benzylo-3-hydroksymetyloindazolu PL PL PL PL PL PL PL PL |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL90283638A PL163720B1 (pl) | 1989-02-07 | 1990-02-05 | Sposób wytwarzania nowych eterowych pochodnych 1-benzylo-3-hydroksymetyloindazolu PL PL PL PL PL PL PL PL |
Country Status (36)
| Country | Link |
|---|---|
| US (2) | US4999367A (pl) |
| EP (1) | EP0382276B1 (pl) |
| JP (1) | JP2870925B2 (pl) |
| KR (1) | KR0145525B1 (pl) |
| CN (2) | CN1046505C (pl) |
| AR (1) | AR247386A1 (pl) |
| AT (1) | ATE127115T1 (pl) |
| AU (1) | AU624895B2 (pl) |
| BG (1) | BG50273A3 (pl) |
| CA (1) | CA2009503C (pl) |
| CZ (1) | CZ280121B6 (pl) |
| DD (2) | DD295363A5 (pl) |
| DE (2) | DE382276T1 (pl) |
| DK (1) | DK0382276T3 (pl) |
| EG (1) | EG19170A (pl) |
| ES (1) | ES2020171T3 (pl) |
| FI (1) | FI102678B1 (pl) |
| GE (1) | GEP19971030B (pl) |
| GR (2) | GR910300073T1 (pl) |
| HU (1) | HU204793B (pl) |
| IL (1) | IL93132A (pl) |
| IN (1) | IN170957B (pl) |
| IT (1) | IT1230441B (pl) |
| LT (1) | LT3604B (pl) |
| LV (1) | LV10612B (pl) |
| NZ (1) | NZ232258A (pl) |
| PE (1) | PE25091A1 (pl) |
| PH (1) | PH26552A (pl) |
| PL (2) | PL163730B1 (pl) |
| PT (1) | PT93067B (pl) |
| RO (1) | RO106252B1 (pl) |
| RU (3) | RU2066318C1 (pl) |
| SK (1) | SK56390A3 (pl) |
| UA (1) | UA26852C2 (pl) |
| YU (1) | YU47943B (pl) |
| ZA (1) | ZA90644B (pl) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1253703B (it) * | 1991-04-22 | 1995-08-23 | Angelini Francesco Ist Ricerca | Uso di acidi metossi alcanoici dell'indazolo per preparare un farmaco attivo nel trattamento di malattie autoimmunitarie |
| IT1293795B1 (it) * | 1997-07-28 | 1999-03-10 | Angelini Ricerche Spa | Farmaco attivo nel ridurre la produzione di proteina mcp-1 |
| US5943270A (en) * | 1997-11-26 | 1999-08-24 | Intel Corporation | Two-transistor DRAM cell for logic process technology |
| US7514463B2 (en) * | 2004-08-20 | 2009-04-07 | University Of Kansas | Lonidamine analogues and their use in male contraception and cancer treatment |
| ITMI20062254A1 (it) * | 2006-11-24 | 2008-05-25 | Acraf | Uso di un acido metossi-alcanoico dell'indazolo per preparare una composizione farmaceutca |
| CA2714436C (en) | 2008-03-07 | 2017-06-27 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. | Novel 1-benzyl-3-hydroxymethylindazole derivatives and use thereof in the treatment of diseases based on the expression of mcp-1, cx3cr1 and p40 |
| EP2262777B8 (en) | 2008-03-07 | 2016-05-04 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.p.A. | 1-benzyl-3-hydroxymethylindazole derivatives and use thereof in the treatment of diseases based on the expression of mcp-1 and cx3cr1 |
| CN101952256B (zh) * | 2008-03-07 | 2016-03-16 | 方济各安吉利克化学联合股份有限公司 | 1-苄基-3-羟基甲基吲唑衍生物及其在治疗基于MCP-1、CX3CR1和p40表达的疾病中的用途 |
| EA019672B1 (ru) * | 2009-08-03 | 2014-05-30 | Ацьенде Кимике Рьюните Анджелини Франческо A.K.P.A.Ф. С.П.А. | Способ получения 1-бензил-3-гидроксиметил-1н-индазола и его производных и необходимые промежуточные соединения, содержащие магний |
| UA108742C2 (uk) * | 2009-09-23 | 2015-06-10 | Фармацевтична композиція для лікування запальних захворювань, опосередкованих mcp-1 | |
| US8999292B2 (en) | 2012-05-01 | 2015-04-07 | Translatum Medicus Inc. | Methods for treating and diagnosing blinding eye diseases |
| CN104334173B (zh) | 2012-05-01 | 2017-05-03 | 特兰斯拉图姆医学公司 | 用于治疗和诊断致盲性眼病的方法 |
| AU2013261718B2 (en) | 2012-05-18 | 2017-10-19 | Sanofi | Pyrazole derivatives and their use as LPAR5 antagonists |
| EP2850062B1 (en) | 2012-05-18 | 2017-07-19 | Sanofi | Pyridine derivatives and their use in the treatment of conditions associated with pathological thrombus formation |
| CN108047136B (zh) * | 2017-12-20 | 2021-07-09 | 长春普华制药股份有限公司 | 一种苄达酸的精制方法 |
| EP3990433A4 (en) | 2019-06-25 | 2023-07-26 | Translatum Medicus Inc. | METHODS FOR THE MANUFACTURE OF 2-((1-BENZYL-1H-INDAZOL-3-YL)METHOXY)-2-METHYLPROPANOIC ACID AND ITS DERIVATIVES |
| CN113929627A (zh) * | 2021-10-19 | 2022-01-14 | 吕梁学院 | 一种宾达利的合成方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL28032A (en) * | 1966-08-29 | 1971-08-25 | Acraf | Indazol-3-yl-oxyalkanoic acids and process for the preparation thereof |
| US3470298A (en) * | 1969-01-29 | 1969-09-30 | Acraf | Topical anti-inflammatory composition containing (indazole-3-yl)-oxyalkanoic acids |
| IT1131779B (it) | 1980-07-29 | 1986-06-25 | Acraf | Sale dell'acido (1-benzil-1h-indazol-3-il)-ossiacetico con la lisina e procedimento per la sua preparazione |
| IT1189052B (it) | 1981-11-27 | 1988-01-28 | Acraf | Trattamento della cataratta |
| IT1194564B (it) | 1983-04-18 | 1988-09-22 | Acraf | Impiego del bendazac e dei suoi sali nel trattamento della retinite pigmentosa |
| IT1197805B (it) | 1986-08-01 | 1988-12-06 | Acraf | Metodo per il tratamento di lenti a contatto |
-
1989
- 1989-02-07 IT IT8947620A patent/IT1230441B/it active
-
1990
- 1990-01-22 IL IL9313290A patent/IL93132A/en not_active IP Right Cessation
- 1990-01-23 DE DE199090200167T patent/DE382276T1/de active Pending
- 1990-01-23 EP EP90200167A patent/EP0382276B1/en not_active Expired - Lifetime
- 1990-01-23 AT AT90200167T patent/ATE127115T1/de not_active IP Right Cessation
- 1990-01-23 ES ES90200167T patent/ES2020171T3/es not_active Expired - Lifetime
- 1990-01-23 DE DE69021902T patent/DE69021902T2/de not_active Expired - Lifetime
- 1990-01-23 DK DK90200167.6T patent/DK0382276T3/da active
- 1990-01-24 US US07/470,118 patent/US4999367A/en not_active Expired - Lifetime
- 1990-01-26 NZ NZ232258A patent/NZ232258A/en unknown
- 1990-01-29 ZA ZA90644A patent/ZA90644B/xx unknown
- 1990-01-30 PE PE1990164654A patent/PE25091A1/es unknown
- 1990-01-30 IN IN81/CAL/90A patent/IN170957B/en unknown
- 1990-02-02 AU AU49066/90A patent/AU624895B2/en not_active Expired
- 1990-02-05 RO RO144074A patent/RO106252B1/ro unknown
- 1990-02-05 YU YU20690A patent/YU47943B/sh unknown
- 1990-02-05 PL PL90285287A patent/PL163730B1/pl unknown
- 1990-02-05 PL PL90283638A patent/PL163720B1/pl unknown
- 1990-02-06 PH PH40002A patent/PH26552A/en unknown
- 1990-02-06 UA UA4743128A patent/UA26852C2/uk unknown
- 1990-02-06 RU SU904743128A patent/RU2066318C1/ru active
- 1990-02-06 PT PT93067A patent/PT93067B/pt active IP Right Grant
- 1990-02-06 BG BG091122A patent/BG50273A3/xx unknown
- 1990-02-06 AR AR90316095A patent/AR247386A1/es active
- 1990-02-06 EG EG6290A patent/EG19170A/xx active
- 1990-02-06 HU HU90689A patent/HU204793B/hu unknown
- 1990-02-06 CZ CS90563A patent/CZ280121B6/cs not_active IP Right Cessation
- 1990-02-06 JP JP2027007A patent/JP2870925B2/ja not_active Expired - Lifetime
- 1990-02-06 FI FI900577A patent/FI102678B1/fi active IP Right Grant
- 1990-02-06 SK SK563-90A patent/SK56390A3/sk not_active IP Right Cessation
- 1990-02-07 CA CA002009503A patent/CA2009503C/en not_active Expired - Lifetime
- 1990-02-07 CN CN90100599A patent/CN1046505C/zh not_active Expired - Fee Related
- 1990-02-07 DD DD90342349A patent/DD295363A5/de unknown
- 1990-02-07 DD DD90337657A patent/DD291995A5/de unknown
- 1990-02-07 KR KR1019900001453A patent/KR0145525B1/ko not_active IP Right Cessation
- 1990-12-20 US US07/632,117 patent/US5112986A/en not_active Expired - Lifetime
-
1991
- 1991-06-05 RU SU914895526A patent/RU2055071C1/ru active
- 1991-06-05 RU SU914895540A patent/RU2044729C1/ru active
- 1991-11-15 GR GR91300073T patent/GR910300073T1/el unknown
-
1993
- 1993-06-22 LV LVP-93-647A patent/LV10612B/lv unknown
- 1993-07-26 GE GEAP19931214A patent/GEP19971030B/en unknown
- 1993-08-17 LT LTIP872A patent/LT3604B/lt not_active IP Right Cessation
- 1993-09-15 CN CN93117740A patent/CN1034016C/zh not_active Expired - Fee Related
-
1995
- 1995-11-22 GR GR950403284T patent/GR3018165T3/el unknown
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