CA1131234A - Basic thio-indazoles - Google Patents
Basic thio-indazolesInfo
- Publication number
- CA1131234A CA1131234A CA345,682A CA345682A CA1131234A CA 1131234 A CA1131234 A CA 1131234A CA 345682 A CA345682 A CA 345682A CA 1131234 A CA1131234 A CA 1131234A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- benzyl
- dimethylaminopropylthio
- indazole
- 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
- 238000000034 method Methods 0.000 claims abstract description 47
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 230000008569 process Effects 0.000 claims abstract description 40
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- VPMZGRVNLHDREW-UHFFFAOYSA-N 3-(2-benzylindazol-3-yl)sulfanyl-n,n-dimethylpropan-1-amine Chemical compound N1=C2C=CC=CC2=C(SCCCN(C)C)N1CC1=CC=CC=C1 VPMZGRVNLHDREW-UHFFFAOYSA-N 0.000 claims abstract 22
- 238000006243 chemical reaction Methods 0.000 claims description 14
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 5
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229940045803 cuprous chloride Drugs 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 3
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 19
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
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- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzydamine Chemical compound C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 description 22
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- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 10
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- 238000010438 heat treatment Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
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- 230000035515 penetration Effects 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 229960002895 phenylbutazone Drugs 0.000 description 5
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 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 4
- -1 acetyl- Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 239000012454 non-polar solvent Substances 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 230000000699 topical effect Effects 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 3
- WHWSDZHLYUEYMX-UHFFFAOYSA-N 2-benzyl-3-(3-chloropropylsulfanyl)indazole Chemical compound N1=C2C=CC=CC2=C(SCCCCl)N1CC1=CC=CC=C1 WHWSDZHLYUEYMX-UHFFFAOYSA-N 0.000 description 3
- VTVTYUPZEYQFFH-UHFFFAOYSA-N 3-(2-benzylindazol-3-yl)sulfanylpropan-1-ol Chemical compound N1=C2C=CC=CC2=C(SCCCO)N1CC1=CC=CC=C1 VTVTYUPZEYQFFH-UHFFFAOYSA-N 0.000 description 3
- LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 description 3
- 206010002091 Anaesthesia Diseases 0.000 description 3
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- 229960001138 acetylsalicylic acid Drugs 0.000 description 3
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- 235000010418 carrageenan Nutrition 0.000 description 3
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- 230000009885 systemic effect Effects 0.000 description 3
- 230000001562 ulcerogenic effect Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
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- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
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- 230000000249 desinfective effect Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
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- 230000008595 infiltration Effects 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- POXOCNLHCWFIEX-UHFFFAOYSA-N 2-benzyl-3-chloroindazole Chemical compound N1=C2C=CC=CC2=C(Cl)N1CC1=CC=CC=C1 POXOCNLHCWFIEX-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UHFFFAOYSA-N 2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound OCC1OC(CO)(OC2OC(CO)C(O)C(O)C2O)C(O)C1O CZMRCDWAGMRECN-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 description 1
- HCEREWKVPIQLGP-UHFFFAOYSA-N 3-(dimethylamino)propane-1-thiol;hydrochloride Chemical compound [Cl-].C[NH+](C)CCCS HCEREWKVPIQLGP-UHFFFAOYSA-N 0.000 description 1
- OZJYYPUOUHCAGX-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropanamide Chemical compound CN(C)C(=O)CCCl OZJYYPUOUHCAGX-UHFFFAOYSA-N 0.000 description 1
- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
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- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
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- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
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- 239000012299 nitrogen atmosphere Substances 0.000 description 1
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000000793 phophlogistic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
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- 238000012552 review Methods 0.000 description 1
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- FZUJWWOKDIGOKH-UHFFFAOYSA-N sulfuric acid hydrochloride Chemical compound Cl.OS(O)(=O)=O FZUJWWOKDIGOKH-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
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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
- 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)
- 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)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20305/79A IT1110282B (it) | 1979-02-19 | 1979-02-19 | Tio-indazoli basici |
| IT20305A/79 | 1979-02-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1131234A true CA1131234A (en) | 1982-09-07 |
Family
ID=11165582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA345,682A Expired CA1131234A (en) | 1979-02-19 | 1980-02-14 | Basic thio-indazoles |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4264618A (enExample) |
| JP (1) | JPS605590B2 (enExample) |
| AT (1) | ATA91780A (enExample) |
| AU (1) | AU518489B2 (enExample) |
| CA (1) | CA1131234A (enExample) |
| DD (2) | DD157255A5 (enExample) |
| DE (1) | DE3000690A1 (enExample) |
| DK (1) | DK69880A (enExample) |
| ES (1) | ES488719A0 (enExample) |
| FI (1) | FI800295A7 (enExample) |
| FR (3) | FR2453156A1 (enExample) |
| GB (3) | GB2043069B (enExample) |
| HU (1) | HU184721B (enExample) |
| IE (1) | IE49399B1 (enExample) |
| IL (1) | IL59271A0 (enExample) |
| IT (1) | IT1110282B (enExample) |
| NL (1) | NL8000610A (enExample) |
| PL (1) | PL130717B1 (enExample) |
| PT (1) | PT70835A (enExample) |
| SE (1) | SE8001279L (enExample) |
| SU (1) | SU1042614A3 (enExample) |
| YU (3) | YU39880A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6190642B1 (en) | 1988-02-19 | 2001-02-20 | Dentsply Research & Development Corp. | Irrigating and lavage compositions |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3145215A (en) * | 1961-12-19 | 1964-08-18 | Sterling Drug Inc | Indazole derivatives |
| GB1054833A (enExample) * | 1963-08-09 | |||
| US3428634A (en) * | 1965-03-13 | 1969-02-18 | Acraf | 3-tertiary amino alkoxy-1-hydrocarbon indazoles |
| US3637738A (en) * | 1969-02-12 | 1972-01-25 | Ciba Geigy Corp | Cycloalkano(c)pyrazole ethers |
| US4182769A (en) * | 1977-02-09 | 1980-01-08 | E. I. Du Pont De Nemours And Company | Anti-inflammatory 1-substituted-4,5-diaryl-2-(substituted-thio) imidazoles and their corresponding sulfoxides and sulfones |
-
1979
- 1979-02-19 IT IT20305/79A patent/IT1110282B/it active
- 1979-12-11 US US06/102,509 patent/US4264618A/en not_active Expired - Lifetime
-
1980
- 1980-01-10 DE DE19803000690 patent/DE3000690A1/de not_active Withdrawn
- 1980-01-30 IL IL59271A patent/IL59271A0/xx unknown
- 1980-01-31 NL NL8000610A patent/NL8000610A/nl not_active Application Discontinuation
- 1980-01-31 FI FI800295A patent/FI800295A7/fi not_active Application Discontinuation
- 1980-02-06 FR FR8002622A patent/FR2453156A1/fr active Granted
- 1980-02-07 AU AU55318/80A patent/AU518489B2/en not_active Ceased
- 1980-02-14 YU YU00398/80A patent/YU39880A/xx unknown
- 1980-02-14 CA CA345,682A patent/CA1131234A/en not_active Expired
- 1980-02-14 GB GB8005082A patent/GB2043069B/en not_active Expired
- 1980-02-15 PT PT70835A patent/PT70835A/pt unknown
- 1980-02-18 DK DK69880A patent/DK69880A/da not_active Application Discontinuation
- 1980-02-18 SE SE8001279A patent/SE8001279L/xx not_active Application Discontinuation
- 1980-02-18 ES ES488719A patent/ES488719A0/es active Granted
- 1980-02-18 IE IE296/80A patent/IE49399B1/en unknown
- 1980-02-18 SU SU802883703A patent/SU1042614A3/ru active
- 1980-02-18 JP JP55018946A patent/JPS605590B2/ja not_active Expired
- 1980-02-18 PL PL1980222090A patent/PL130717B1/pl unknown
- 1980-02-18 HU HU80367A patent/HU184721B/hu unknown
- 1980-02-19 AT AT0091780A patent/ATA91780A/de not_active IP Right Cessation
- 1980-02-19 DD DD80228371A patent/DD157255A5/de unknown
- 1980-02-19 DD DD80219140A patent/DD149806A5/de unknown
- 1980-07-03 FR FR8014867A patent/FR2450823A1/fr active Granted
- 1980-07-03 FR FR8014866A patent/FR2450822A1/fr active Granted
-
1982
- 1982-10-15 GB GB08229492A patent/GB2108957B/en not_active Expired
- 1982-10-15 GB GB08229493A patent/GB2108958B/en not_active Expired
- 1982-11-22 YU YU02606/82A patent/YU260682A/xx unknown
- 1982-11-22 YU YU02605/82A patent/YU260582A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |