DE382276T1 - 1-benzyl-3-hydroxymethylindazol-aether mit aliphatischen 2-hydroxysaeuren. - Google Patents
1-benzyl-3-hydroxymethylindazol-aether mit aliphatischen 2-hydroxysaeuren.Info
- Publication number
- DE382276T1 DE382276T1 DE199090200167T DE90200167T DE382276T1 DE 382276 T1 DE382276 T1 DE 382276T1 DE 199090200167 T DE199090200167 T DE 199090200167T DE 90200167 T DE90200167 T DE 90200167T DE 382276 T1 DE382276 T1 DE 382276T1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compound
- already mentioned
- crr
- meanings already
- 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.)
- Pending
Links
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 15
- 238000000034 method Methods 0.000 claims 11
- 239000002904 solvent Substances 0.000 claims 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- 238000009835 boiling Methods 0.000 claims 5
- 238000007796 conventional method Methods 0.000 claims 5
- 239000011541 reaction mixture Substances 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- 239000002585 base Substances 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- -1 aliphatic saturated alcohol Chemical class 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 244000309464 bull Species 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229960001701 chloroform Drugs 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 239000012280 lithium aluminium hydride Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910000105 potassium hydride Inorganic materials 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Ophthalmology & Optometry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
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 |
|---|---|
| DE382276T1 true DE382276T1 (de) | 1991-11-28 |
Family
ID=11261479
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE199090200167T Pending DE382276T1 (de) | 1989-02-07 | 1990-01-23 | 1-benzyl-3-hydroxymethylindazol-aether mit aliphatischen 2-hydroxysaeuren. |
| DE69021902T Expired - Lifetime DE69021902T2 (de) | 1989-02-07 | 1990-01-23 | 1-Benzyl-3-hydroxymethylindazol-Äther mit aliphatischen 2-Hydroxysäuren. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69021902T Expired - Lifetime DE69021902T2 (de) | 1989-02-07 | 1990-01-23 | 1-Benzyl-3-hydroxymethylindazol-Äther mit aliphatischen 2-Hydroxysäuren. |
Country Status (36)
| Country | Link |
|---|---|
| US (2) | US4999367A (Direct) |
| EP (1) | EP0382276B1 (Direct) |
| JP (1) | JP2870925B2 (Direct) |
| KR (1) | KR0145525B1 (Direct) |
| CN (2) | CN1046505C (Direct) |
| AR (1) | AR247386A1 (Direct) |
| AT (1) | ATE127115T1 (Direct) |
| AU (1) | AU624895B2 (Direct) |
| BG (1) | BG50273A3 (Direct) |
| CA (1) | CA2009503C (Direct) |
| CZ (1) | CZ280121B6 (Direct) |
| DD (2) | DD291995A5 (Direct) |
| DE (2) | DE382276T1 (Direct) |
| DK (1) | DK0382276T3 (Direct) |
| EG (1) | EG19170A (Direct) |
| ES (1) | ES2020171T3 (Direct) |
| FI (1) | FI102678B1 (Direct) |
| GE (1) | GEP19971030B (Direct) |
| GR (2) | GR910300073T1 (Direct) |
| HU (1) | HU204793B (Direct) |
| IL (1) | IL93132A (Direct) |
| IN (1) | IN170957B (Direct) |
| IT (1) | IT1230441B (Direct) |
| LT (1) | LT3604B (Direct) |
| LV (1) | LV10612B (Direct) |
| NZ (1) | NZ232258A (Direct) |
| PE (1) | PE25091A1 (Direct) |
| PH (1) | PH26552A (Direct) |
| PL (2) | PL163730B1 (Direct) |
| PT (1) | PT93067B (Direct) |
| RO (1) | RO106252B1 (Direct) |
| RU (3) | RU2066318C1 (Direct) |
| SK (1) | SK56390A3 (Direct) |
| UA (1) | UA26852C2 (Direct) |
| YU (1) | YU47943B (Direct) |
| ZA (1) | ZA90644B (Direct) |
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 |
| EP2262778B8 (en) | 2008-03-07 | 2020-01-01 | 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, cx3cr1 and p40 |
| KR101581828B1 (ko) * | 2008-03-07 | 2015-12-31 | 아지엔드 키미쉐 리유나이트 안젤리니 프란체스코 에이.씨.알.에이.에프. 에스.피.에이 | 신규한 1-벤질-3-하이드록시메틸인다졸 유도체들 및 ｍｃｐ-1, ｃｘ3ｃｒ1 및 ｐ40의 발현을 기초로 한 질환들의 치료에서 이의 용도 |
| KR101581829B1 (ko) | 2008-03-07 | 2015-12-31 | 아지엔드 키미쉐 리유나이트 안젤리니 프란체스코 에이.씨.알.에이.에프. 에스.피.에이 | 1-벤질-3-하이드록시메틸인다졸 유도체들 및 ｍｃｐ-1 및 ｃｘ3ｃｒ1의 발현을 기초로 한 질환들의 치료에서 이의 용도 |
| SG176885A1 (en) * | 2009-08-03 | 2012-01-30 | Acraf | Process for the preparation of 1-benzyl-3-hydr0xymethyl-1h-indaz0le and its derivatives and required magnesium intermediates |
| 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 |
| EP3338776A1 (en) | 2012-05-01 | 2018-06-27 | Translatum Medicus Inc. | Methods for treating and diagnosing blinding eye diseases |
| US9346757B2 (en) | 2012-05-18 | 2016-05-24 | Sanofi | Pyridine derivatives and their use in the treatment of conditions associated with pathological thrombus formation |
| JP6257596B2 (ja) | 2012-05-18 | 2018-01-10 | サノフイ | ピラゾール誘導体およびｌｐａｒ５アンタゴニストとしてのその使用 |
| 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 |
| EP3990433B1 (en) * | 2019-06-25 | 2026-05-20 | Translatum Medicus Inc | PROCESSES 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 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 EP EP90200167A patent/EP0382276B1/en not_active Expired - Lifetime
- 1990-01-23 DK DK90200167.6T patent/DK0382276T3/da active
- 1990-01-23 DE DE199090200167T patent/DE382276T1/de active Pending
- 1990-01-23 DE DE69021902T patent/DE69021902T2/de not_active Expired - Lifetime
- 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 IN IN81/CAL/90A patent/IN170957B/en unknown
- 1990-01-30 PE PE1990164654A patent/PE25091A1/es unknown
- 1990-02-02 AU AU49066/90A patent/AU624895B2/en not_active Expired
- 1990-02-05 YU YU20690A patent/YU47943B/sh unknown
- 1990-02-05 PL PL90285287A patent/PL163730B1/pl unknown
- 1990-02-05 RO RO144074A patent/RO106252B1/ro unknown
- 1990-02-05 PL PL90283638A patent/PL163720B1/pl unknown
- 1990-02-06 JP JP2027007A patent/JP2870925B2/ja not_active Expired - Lifetime
- 1990-02-06 HU HU90689A patent/HU204793B/hu unknown
- 1990-02-06 AR AR90316095A patent/AR247386A1/es active
- 1990-02-06 UA UA4743128A patent/UA26852C2/uk unknown
- 1990-02-06 RU SU904743128A patent/RU2066318C1/ru active
- 1990-02-06 BG BG091122A patent/BG50273A3/xx unknown
- 1990-02-06 PT PT93067A patent/PT93067B/pt active IP Right Grant
- 1990-02-06 EG EG6290A patent/EG19170A/xx active
- 1990-02-06 PH PH40002A patent/PH26552A/en unknown
- 1990-02-06 SK SK563-90A patent/SK56390A3/sk not_active IP Right Cessation
- 1990-02-06 CZ CS90563A patent/CZ280121B6/cs not_active IP Right Cessation
- 1990-02-06 FI FI900577A patent/FI102678B1/fi active IP Right Grant
- 1990-02-07 DD DD90337657A patent/DD291995A5/de unknown
- 1990-02-07 KR KR1019900001453A patent/KR0145525B1/ko not_active Expired - Fee Related
- 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 CA CA002009503A patent/CA2009503C/en not_active Expired - Lifetime
- 1990-12-20 US US07/632,117 patent/US5112986A/en not_active Expired - Lifetime
-
1991
- 1991-06-05 RU SU914895540A patent/RU2044729C1/ru active
- 1991-06-05 RU SU914895526A patent/RU2055071C1/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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