FI110939B - N-substituoitu-1-alkyylitio-2-nitroeteeniamiinin ja sen suolan valmistus - Google Patents
N-substituoitu-1-alkyylitio-2-nitroeteeniamiinin ja sen suolan valmistus Download PDFInfo
- Publication number
- FI110939B FI110939B FI901696A FI901696A FI110939B FI 110939 B FI110939 B FI 110939B FI 901696 A FI901696 A FI 901696A FI 901696 A FI901696 A FI 901696A FI 110939 B FI110939 B FI 110939B
- Authority
- FI
- Finland
- Prior art keywords
- formula
- dimethylaminomethyl
- process according
- methyl
- compound
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 13
- 150000003839 salts Chemical class 0.000 title description 4
- -1 heterocyclic alkylamines Chemical group 0.000 claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 150000001412 amines Chemical class 0.000 claims abstract description 10
- ULOTWPOKIYOEQN-UHFFFAOYSA-N 2-nitroethanedithioic acid Chemical compound [O-][N+](=O)CC(S)=S ULOTWPOKIYOEQN-UHFFFAOYSA-N 0.000 claims abstract description 8
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 claims abstract description 8
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 24
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 23
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 6
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical group COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims 2
- 229940100198 alkylating agent Drugs 0.000 claims 2
- 239000012022 methylating agents Substances 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- YQFHPXZGXNYYLD-UHFFFAOYSA-N n-methyl-1-methylsulfanyl-2-nitroethenamine Chemical compound CNC(SC)=C[N+]([O-])=O YQFHPXZGXNYYLD-UHFFFAOYSA-N 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 abstract description 6
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 2
- ZILSBZLQGRBMOR-UHFFFAOYSA-N 1,3-benzodioxol-5-ylmethanamine Chemical compound NCC1=CC=C2OCOC2=C1 ZILSBZLQGRBMOR-UHFFFAOYSA-N 0.000 abstract 1
- DXSUORGKJZADET-UHFFFAOYSA-N 3,3-dimethylbutan-2-amine Chemical compound CC(N)C(C)(C)C DXSUORGKJZADET-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 150000003975 aryl alkyl amines Chemical group 0.000 abstract 1
- 125000005343 heterocyclic alkyl group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HRCSDUZVYNAMRQ-UHFFFAOYSA-L dipotassium;2-nitroethanedithioate Chemical compound [K+].[K+].[O-][N+](=O)CC([S-])=S.[O-][N+](=O)CC([S-])=S HRCSDUZVYNAMRQ-UHFFFAOYSA-L 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 238000005576 amination reaction Methods 0.000 description 3
- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 3
- 229960000620 ranitidine Drugs 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- YDFYTQPYSUXHID-UHFFFAOYSA-N [O-][N+](=O)CC(S)=S.[O-][N+](=O)C=C(S)S Chemical compound [O-][N+](=O)CC(S)=S.[O-][N+](=O)C=C(S)S YDFYTQPYSUXHID-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- LFQRKUIOSYPVFY-UHFFFAOYSA-L dipotassium diacetate Chemical compound [K+].[K+].CC([O-])=O.CC([O-])=O LFQRKUIOSYPVFY-UHFFFAOYSA-L 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- RFXJCBMXMNUGPM-UHFFFAOYSA-N n-methyl-1-methylsulfanyl-2-nitroethanamine Chemical compound CNC(SC)C[N+]([O-])=O RFXJCBMXMNUGPM-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/27—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and unsaturated
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Luminescent Compositions (AREA)
- Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Underground Structures, Protecting, Testing And Restoring Foundations (AREA)
- Ultra Sonic Daignosis Equipment (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB898907700A GB8907700D0 (en) | 1989-04-05 | 1989-04-05 | Preparation of substituted ethenes |
| GB8907700 | 1989-04-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI901696A0 FI901696A0 (fi) | 1990-04-04 |
| FI110939B true FI110939B (fi) | 2003-04-30 |
Family
ID=10654520
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI901696A FI110939B (fi) | 1989-04-05 | 1990-04-04 | N-substituoitu-1-alkyylitio-2-nitroeteeniamiinin ja sen suolan valmistus |
| FI914672A FI914672A0 (fi) | 1989-04-05 | 1991-10-04 | Framstaellning av substituerade eten. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI914672A FI914672A0 (fi) | 1989-04-05 | 1991-10-04 | Framstaellning av substituerade eten. |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US5371247A (es) |
| EP (1) | EP0466733B1 (es) |
| JP (2) | JP2954270B2 (es) |
| KR (2) | KR920701140A (es) |
| AT (2) | AT400030B (es) |
| BE (1) | BE1003124A5 (es) |
| CA (2) | CA2013841C (es) |
| CH (1) | CH681008A5 (es) |
| DE (2) | DE69011677T2 (es) |
| DK (2) | DK84390A (es) |
| ES (2) | ES2019246A6 (es) |
| FI (2) | FI110939B (es) |
| FR (1) | FR2645535B1 (es) |
| GB (2) | GB8907700D0 (es) |
| GR (1) | GR1001302B (es) |
| HU (3) | HU9203905D0 (es) |
| IE (2) | IE61894B1 (es) |
| IL (1) | IL94002A (es) |
| IN (3) | IN170319B (es) |
| IT (1) | IT1242481B (es) |
| NL (1) | NL194699C (es) |
| PT (1) | PT93659B (es) |
| SE (1) | SE509459C2 (es) |
| WO (1) | WO1990012002A1 (es) |
| ZA (1) | ZA902592B (es) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8907700D0 (en) * | 1989-04-05 | 1989-05-17 | Fine Organics Ltd | Preparation of substituted ethenes |
| PT101031B (pt) * | 1991-11-05 | 2002-07-31 | Transkaryotic Therapies Inc | Processo para o fornecimento de proteinas por terapia genetica |
| US5686588A (en) * | 1995-08-16 | 1997-11-11 | Yoo; Seo Hong | Amine acid salt compounds and process for the production thereof |
| AU2001264174A1 (en) | 2000-04-21 | 2001-11-07 | Ioannis Pallikaris | Device for the shaping of a substance on the surface of a cornea |
| CN104119257B (zh) * | 2013-04-26 | 2016-08-03 | 石家庄康坦福化工科技有限公司 | 一种1-甲胺基-1-甲硫基-2-硝基乙烯的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1554153A (en) * | 1975-05-15 | 1979-10-17 | Smith Kline French Lab | Process for making 2-amino-2-alkylthionitroethylenes |
| IT1168163B (it) * | 1981-08-18 | 1987-05-20 | Ausonia Farma Srl | Composto ad attivita' antiulcera, procedimento per la sua preparazione e composizioni farmaceutiche relative |
| PT76557B (en) * | 1982-04-16 | 1986-01-21 | Inke Sa | Process for preparing furan derivatives and addition salts thereof and of pharmaceutical compositions containing the same |
| ES8500618A1 (es) * | 1983-06-21 | 1984-11-16 | Union Quimico Farma | Procedimiento para la obtencion de n-metil-1-metiltio-2-nitroetenamina |
| GB8415254D0 (en) * | 1984-06-15 | 1984-07-18 | Glaxo Group Ltd | Amine derivatives |
| ES2003781A6 (es) * | 1987-02-06 | 1988-11-16 | Unio Quimico Farmaceutica S A | Procedimiento para la obtencion de n-metil-1-metiltio-2-nitroetenamina |
| GB8907700D0 (en) * | 1989-04-05 | 1989-05-17 | Fine Organics Ltd | Preparation of substituted ethenes |
-
1989
- 1989-04-05 GB GB898907700A patent/GB8907700D0/en active Pending
- 1989-04-05 HU HU9203905A patent/HU9203905D0/hu unknown
-
1990
- 1990-04-04 KR KR1019910700948A patent/KR920701140A/ko not_active Application Discontinuation
- 1990-04-04 US US07/730,963 patent/US5371247A/en not_active Expired - Fee Related
- 1990-04-04 ZA ZA902592A patent/ZA902592B/xx unknown
- 1990-04-04 BE BE9000381A patent/BE1003124A5/fr not_active IP Right Cessation
- 1990-04-04 IN IN247/MAS/90A patent/IN170319B/en unknown
- 1990-04-04 CH CH1132/90A patent/CH681008A5/fr not_active IP Right Cessation
- 1990-04-04 ES ES9000971A patent/ES2019246A6/es not_active Expired - Fee Related
- 1990-04-04 WO PCT/GB1990/000501 patent/WO1990012002A1/en active IP Right Grant
- 1990-04-04 AT AT0080090A patent/AT400030B/de not_active IP Right Cessation
- 1990-04-04 JP JP2090034A patent/JP2954270B2/ja not_active Expired - Lifetime
- 1990-04-04 GB GB9007568A patent/GB2230526B/en not_active Expired - Lifetime
- 1990-04-04 JP JP2505189A patent/JP3003946B2/ja not_active Expired - Fee Related
- 1990-04-04 IL IL9400290A patent/IL94002A/en not_active IP Right Cessation
- 1990-04-04 DE DE69011677T patent/DE69011677T2/de not_active Expired - Fee Related
- 1990-04-04 CA CA002013841A patent/CA2013841C/en not_active Expired - Lifetime
- 1990-04-04 US US07/503,987 patent/US5112995A/en not_active Expired - Lifetime
- 1990-04-04 DK DK084390A patent/DK84390A/da not_active Application Discontinuation
- 1990-04-04 HU HU902080A patent/HU207991B/hu unknown
- 1990-04-04 KR KR1019900004645A patent/KR0147820B1/ko not_active IP Right Cessation
- 1990-04-04 GR GR900100250A patent/GR1001302B/el not_active IP Right Cessation
- 1990-04-04 SE SE9001236A patent/SE509459C2/sv not_active IP Right Cessation
- 1990-04-04 FR FR909004313A patent/FR2645535B1/fr not_active Expired - Lifetime
- 1990-04-04 HU HU902945A patent/HUT58285A/hu unknown
- 1990-04-04 DE DE4010888A patent/DE4010888C2/de not_active Expired - Lifetime
- 1990-04-04 DK DK90905245.8T patent/DK0466733T3/da active
- 1990-04-04 ES ES90905245T patent/ES2057549T3/es not_active Expired - Lifetime
- 1990-04-04 AT AT90905245T patent/ATE110055T1/de not_active IP Right Cessation
- 1990-04-04 IT IT04782990A patent/IT1242481B/it active IP Right Grant
- 1990-04-04 IE IE122290A patent/IE61894B1/en not_active IP Right Cessation
- 1990-04-04 PT PT93659A patent/PT93659B/pt not_active IP Right Cessation
- 1990-04-04 CA CA002046293A patent/CA2046293C/en not_active Expired - Fee Related
- 1990-04-04 EP EP90905245A patent/EP0466733B1/en not_active Expired - Lifetime
- 1990-04-04 IE IE122190A patent/IE65395B1/en not_active IP Right Cessation
- 1990-04-04 NL NL9000790A patent/NL194699C/nl not_active IP Right Cessation
- 1990-04-04 FI FI901696A patent/FI110939B/fi active IP Right Grant
-
1991
- 1991-10-04 FI FI914672A patent/FI914672A0/fi not_active Application Discontinuation
- 1991-11-25 IN IN872MA1991 patent/IN173648B/en unknown
- 1991-11-25 IN IN871MA1991 patent/IN173647B/en unknown
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