CS250240B2 - Method of ethandiimidamide's derivatives production - Google Patents
Method of ethandiimidamide's derivatives production Download PDFInfo
- Publication number
- CS250240B2 CS250240B2 CS841958A CS195884A CS250240B2 CS 250240 B2 CS250240 B2 CS 250240B2 CS 841958 A CS841958 A CS 841958A CS 195884 A CS195884 A CS 195884A CS 250240 B2 CS250240 B2 CS 250240B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- ethanediimidamide
- formula
- hydrogen
- atom
- carbon atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- RDJGIQPSSNMJPF-UHFFFAOYSA-N ethanediimidamide Chemical class NC(=N)C(N)=N RDJGIQPSSNMJPF-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000005943 1,2,3,6-tetrahydropyridyl group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- -1 5-dimethylaminomethyl-4-methyl-2-thienyl Chemical group 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 150000004677 hydrates Chemical class 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000012453 solvate Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 239000000523 sample Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000006308 propyl amino group Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000003386 piperidinyl group Chemical group 0.000 description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- IPLXKLUYTPGIPL-UHFFFAOYSA-N 1,2,5-thiadiazole-3,4-diamine Chemical class NC1=NSN=C1N IPLXKLUYTPGIPL-UHFFFAOYSA-N 0.000 description 1
- ALOVQGMDXUFLEB-UHFFFAOYSA-N 1-oxo-1,2,5-thiadiazol-3-amine Chemical compound NC=1C=NS(=O)N=1 ALOVQGMDXUFLEB-UHFFFAOYSA-N 0.000 description 1
- GXZDYRYYNXYPMQ-UHFFFAOYSA-N 2-chloro-6-methylpyridine Chemical compound CC1=CC=CC(Cl)=N1 GXZDYRYYNXYPMQ-UHFFFAOYSA-N 0.000 description 1
- YBLPTIHIBXOVDM-UHFFFAOYSA-N 2-n'-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethyl]ethanediimidamide Chemical compound CN(C)CC1=CC=C(CSCCNC(=N)C(N)=N)O1 YBLPTIHIBXOVDM-UHFFFAOYSA-N 0.000 description 1
- MDAGFERLPSGSPT-UHFFFAOYSA-N 2-n'-[2-[[5-[(dimethylamino)methyl]thiophen-3-yl]methylsulfanyl]ethyl]ethanediimidamide Chemical compound CN(C)CC1=CC(CSCCNC(=N)C(N)=N)=CS1 MDAGFERLPSGSPT-UHFFFAOYSA-N 0.000 description 1
- GCPNDUGDDPCEAY-UHFFFAOYSA-N 2-n'-[2-[[5-[(dimethylamino)methyl]thiophen-3-yl]methylsulfanyl]ethyl]ethanediimidamide;trihydrochloride Chemical compound Cl.Cl.Cl.CN(C)CC1=CC(CSCCNC(=N)C(N)=N)=CS1 GCPNDUGDDPCEAY-UHFFFAOYSA-N 0.000 description 1
- VRALOCFIFDRXTC-UHFFFAOYSA-N 2-n'-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]ethanediimidamide Chemical compound NC(=N)C(=N)NCCCOC1=CC=CC(CN2CCCCC2)=C1 VRALOCFIFDRXTC-UHFFFAOYSA-N 0.000 description 1
- ZJISWUHWDYNKFX-UHFFFAOYSA-N 2-n'-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]ethanediimidamide;trihydrochloride Chemical compound Cl.Cl.Cl.NC(=N)C(=N)NCCCOC1=CC=CC(CN2CCCCC2)=C1 ZJISWUHWDYNKFX-UHFFFAOYSA-N 0.000 description 1
- IRQUPRKBBWVPAU-UHFFFAOYSA-N 2-n'-[3-[3-(pyrrolidin-1-ylmethyl)phenoxy]propyl]ethanediimidamide Chemical compound NC(=N)C(=N)NCCCOC1=CC=CC(CN2CCCC2)=C1 IRQUPRKBBWVPAU-UHFFFAOYSA-N 0.000 description 1
- LBNPMRUENVBXOR-UHFFFAOYSA-N 2-n'-[3-[4-(piperidin-1-ylmethyl)pyridin-2-yl]oxypropyl]ethanediimidamide Chemical compound C1=NC(OCCCNC(=N)C(=N)N)=CC(CN2CCCCC2)=C1 LBNPMRUENVBXOR-UHFFFAOYSA-N 0.000 description 1
- OETKCBJTZXIZMO-UHFFFAOYSA-N 2-n'-[3-[6-(piperidin-1-ylmethyl)pyridin-2-yl]oxypropyl]ethanediimidamide Chemical compound NC(=N)C(=N)NCCCOC1=CC=CC(CN2CCCCC2)=N1 OETKCBJTZXIZMO-UHFFFAOYSA-N 0.000 description 1
- OHLUAARMJNNWIK-UHFFFAOYSA-N 4-methoxy-1-oxo-1,2,5-thiadiazol-3-amine Chemical compound COC1=NS(=O)N=C1N OHLUAARMJNNWIK-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 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 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36320782A | 1982-03-29 | 1982-03-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS250240B2 true CS250240B2 (en) | 1987-04-16 |
Family
ID=23429274
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS832191A CS250229B2 (en) | 1982-03-29 | 1983-03-29 | Method of 3,4-diamino-1,2,5-thiadiazole derivatives' production |
| CS841958A CS250240B2 (en) | 1982-03-29 | 1983-03-29 | Method of ethandiimidamide's derivatives production |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS832191A CS250229B2 (en) | 1982-03-29 | 1983-03-29 | Method of 3,4-diamino-1,2,5-thiadiazole derivatives' production |
Country Status (30)
| Country | Link |
|---|---|
| JP (2) | JPS58180477A (en, 2012) |
| KR (1) | KR880002209B1 (en, 2012) |
| AT (1) | AT386599B (en, 2012) |
| AU (2) | AU557577B2 (en, 2012) |
| BE (1) | BE896291A (en, 2012) |
| CH (2) | CH655111A5 (en, 2012) |
| CS (2) | CS250229B2 (en, 2012) |
| DD (2) | DD219768A5 (en, 2012) |
| DE (1) | DE3311281A1 (en, 2012) |
| DK (2) | DK166677B1 (en, 2012) |
| ES (3) | ES8404683A1 (en, 2012) |
| FR (2) | FR2542741B1 (en, 2012) |
| GB (2) | GB2117769B (en, 2012) |
| GR (1) | GR78524B (en, 2012) |
| HU (2) | HU188742B (en, 2012) |
| IE (1) | IE55596B1 (en, 2012) |
| IL (1) | IL68259A0 (en, 2012) |
| IT (1) | IT1164633B (en, 2012) |
| LU (1) | LU84716A1 (en, 2012) |
| MY (1) | MY8700942A (en, 2012) |
| NL (1) | NL8301063A (en, 2012) |
| NO (1) | NO163055C (en, 2012) |
| NZ (1) | NZ203726A (en, 2012) |
| OA (1) | OA07356A (en, 2012) |
| PT (1) | PT76459B (en, 2012) |
| SE (2) | SE461040B (en, 2012) |
| SU (2) | SU1419518A3 (en, 2012) |
| YU (1) | YU44849B (en, 2012) |
| ZA (1) | ZA832154B (en, 2012) |
| ZW (1) | ZW7683A1 (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2222083A (en) * | 1982-12-14 | 1984-06-21 | Smith Kline & French Laboratories Limited | Pyridine derivatives |
| US4593039A (en) * | 1984-04-02 | 1986-06-03 | Merck & Co., Inc. | 1-aryloxy-3-(substituted aminoalkylamino)-2-propanols |
| US4644006A (en) * | 1984-06-22 | 1987-02-17 | Bristol-Myers Company | Substituted 3,4-diamino-1,2,5-thiadiazoles having histamine H2 -receptor antagonist activity |
| JPH0622828B2 (ja) * | 1986-06-30 | 1994-03-30 | フアナツク株式会社 | 直圧式型締機構 |
| US20230349922A1 (en) | 2020-08-11 | 2023-11-02 | Université De Strasbourg | H2 Blockers Targeting Liver Macrophages for the Prevention and Treatment of Liver Disease and Cancer |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3018289A (en) * | 1960-02-10 | 1962-01-23 | Wyandotte Chemicals Corp | Process for preparing oxamidines |
| GB1595291A (en) * | 1976-09-21 | 1981-08-12 | Smith Kline French Lab | Pyrimidone and thiopyrimidone derivatives |
| FI76795C (fi) * | 1979-09-04 | 1988-12-12 | Bristol Myers Co | Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara 3,4-disubstituerade 1,2,5-tiadiazol-1-oxider och -1,1-dioxider samt nya mellanprodukter. |
| EP0040696B1 (en) * | 1980-04-30 | 1986-08-27 | Merck & Co. Inc. | Aminothiadiazoles as gastric secretion inhibitors |
| AU2222083A (en) * | 1982-12-14 | 1984-06-21 | Smith Kline & French Laboratories Limited | Pyridine derivatives |
-
1983
- 1983-03-25 FR FR838304934A patent/FR2542741B1/fr not_active Expired
- 1983-03-25 ZA ZA832154A patent/ZA832154B/xx unknown
- 1983-03-25 ES ES520982A patent/ES8404683A1/es not_active Expired
- 1983-03-25 NL NL8301063A patent/NL8301063A/nl not_active Application Discontinuation
- 1983-03-25 ZW ZW76/83A patent/ZW7683A1/xx unknown
- 1983-03-28 LU LU84716A patent/LU84716A1/fr unknown
- 1983-03-28 IE IE686/83A patent/IE55596B1/en not_active IP Right Cessation
- 1983-03-28 BE BE0/210417A patent/BE896291A/fr not_active IP Right Cessation
- 1983-03-28 DK DK141383A patent/DK166677B1/da not_active IP Right Cessation
- 1983-03-28 DE DE19833311281 patent/DE3311281A1/de not_active Withdrawn
- 1983-03-28 GB GB08308518A patent/GB2117769B/en not_active Expired
- 1983-03-28 NZ NZ203726A patent/NZ203726A/en unknown
- 1983-03-28 SU SU833568849A patent/SU1419518A3/ru active
- 1983-03-28 AU AU12907/83A patent/AU557577B2/en not_active Ceased
- 1983-03-28 HU HU831040A patent/HU188742B/hu not_active IP Right Cessation
- 1983-03-28 GR GR70903A patent/GR78524B/el unknown
- 1983-03-28 IT IT48005/83A patent/IT1164633B/it active
- 1983-03-28 HU HU854071A patent/HU196386B/hu not_active IP Right Cessation
- 1983-03-28 PT PT76459A patent/PT76459B/pt not_active IP Right Cessation
- 1983-03-28 IL IL68259A patent/IL68259A0/xx not_active IP Right Cessation
- 1983-03-28 SE SE8301725A patent/SE461040B/sv not_active IP Right Cessation
- 1983-03-28 NO NO831100A patent/NO163055C/no unknown
- 1983-03-29 CH CH1749/83A patent/CH655111A5/de not_active IP Right Cessation
- 1983-03-29 AT AT0111083A patent/AT386599B/de not_active IP Right Cessation
- 1983-03-29 JP JP58051740A patent/JPS58180477A/ja active Granted
- 1983-03-29 OA OA57955A patent/OA07356A/xx unknown
- 1983-03-29 CS CS832191A patent/CS250229B2/cs unknown
- 1983-03-29 YU YU744/83A patent/YU44849B/xx unknown
- 1983-03-29 CS CS841958A patent/CS250240B2/cs unknown
- 1983-03-29 CH CH575/86A patent/CH660880A5/de not_active IP Right Cessation
- 1983-03-29 KR KR1019830001283A patent/KR880002209B1/ko not_active Expired
- 1983-03-29 DD DD83260707A patent/DD219768A5/de not_active IP Right Cessation
- 1983-03-29 DD DD83249300A patent/DD210909A5/de not_active IP Right Cessation
- 1983-11-30 ES ES527685A patent/ES8505977A1/es not_active Expired
- 1983-11-30 ES ES527686A patent/ES527686A0/es active Granted
-
1984
- 1984-06-08 SU SU843750493A patent/SU1355123A3/ru active
- 1984-12-31 GB GB08432809A patent/GB2149406B/en not_active Expired
-
1986
- 1986-09-30 AU AU63272/86A patent/AU586037B2/en not_active Ceased
-
1987
- 1987-05-22 FR FR878707197A patent/FR2597867B1/fr not_active Expired
- 1987-11-25 SE SE8704689A patent/SE464302B/sv not_active IP Right Cessation
- 1987-12-30 MY MY942/87A patent/MY8700942A/xx unknown
-
1992
- 1992-06-18 DK DK92811A patent/DK81192D0/da not_active Application Discontinuation
-
1993
- 1993-04-16 JP JP5124585A patent/JPH06135925A/ja active Pending
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