SE451840B - Optiskt rent monohydrat av s-(-)-1-propyl-2',6'-pipekoloxylididhydroklorid, sett att framstella denna och farmaceutiska beredningar for lokalbedovning - Google Patents
Optiskt rent monohydrat av s-(-)-1-propyl-2',6'-pipekoloxylididhydroklorid, sett att framstella denna och farmaceutiska beredningar for lokalbedovningInfo
- Publication number
- SE451840B SE451840B SE8600017A SE8600017A SE451840B SE 451840 B SE451840 B SE 451840B SE 8600017 A SE8600017 A SE 8600017A SE 8600017 A SE8600017 A SE 8600017A SE 451840 B SE451840 B SE 451840B
- Authority
- SE
- Sweden
- Prior art keywords
- propyl
- hydrochloride
- water
- added
- acetone
- Prior art date
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims description 21
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 5
- 238000004873 anchoring Methods 0.000 title 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 14
- 150000004682 monohydrates Chemical class 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 5
- 238000002690 local anesthesia Methods 0.000 claims description 4
- ZKMNUMMKYBVTFN-HNNXBMFYSA-N (S)-ropivacaine Chemical compound CCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C ZKMNUMMKYBVTFN-HNNXBMFYSA-N 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 5
- 229930182837 (R)-adrenaline Natural products 0.000 description 5
- 229960005139 epinephrine Drugs 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- YLXIPWWIOISBDD-NDAAPVSOSA-N (2r,3r)-2,3-dihydroxybutanedioic acid;4-[(1r)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.CNC[C@H](O)C1=CC=C(O)C(O)=C1 YLXIPWWIOISBDD-NDAAPVSOSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (30)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8600017A SE451840B (sv) | 1986-01-03 | 1986-01-03 | Optiskt rent monohydrat av s-(-)-1-propyl-2',6'-pipekoloxylididhydroklorid, sett att framstella denna och farmaceutiska beredningar for lokalbedovning |
| ZA868600A ZA868600B (en) | 1986-01-03 | 1986-11-12 | An optically pure compound and a process for its preparation |
| US06/934,114 US4870086A (en) | 1986-01-03 | 1986-11-24 | Optically pure compound and a process for its preparation |
| EG747/86A EG17867A (en) | 1986-01-03 | 1986-12-02 | Process for the preparation of optically pure compound |
| NO864858A NO170330C (no) | 1986-01-03 | 1986-12-03 | Fremgangsmaate for fremstilling av vesentlig optisk rent monohydrat av s-(-)-propyl-2',6'-pipekoloksylididhydroklorid |
| AU66449/86A AU592392B2 (en) | 1986-01-03 | 1986-12-12 | S-(-)-1-propyl-2', 6' pipecoloxylidide hydrochloride monohydrate and a method for its preparation |
| NZ218615A NZ218615A (en) | 1986-01-03 | 1986-12-12 | S-(-)-1-propyl-2',6'-pipecoloxylidide hydrochloride monohydrate and local anesthesia compositions |
| DE8686850440T DE3674582D1 (de) | 1986-01-03 | 1986-12-15 | (s)-(-)-1-propyl-2',6'-pipecoloxylidid-hydrochloridmonohydrat, verfahren zu seiner herstellung und es enthaltendes pharmazeutisches praeparat. |
| EP86850440A EP0239710B1 (en) | 1986-01-03 | 1986-12-15 | (s)-(-)-1-propyl-2',6'-pipecoloxylidide hydrochloride monohydrate, process for its preparation and pharmaceutical preparation containing it |
| PH34593A PH22924A (en) | 1986-01-03 | 1986-12-15 | Optically pure monohydrate of s-(-)-1-propyl-2',6' pipecoloxylidide hydrochloride and a process for its preparation |
| AT86850440T ATE56956T1 (de) | 1986-01-03 | 1986-12-15 | (s)-(-)-1-propyl-2',6'-pipecoloxylididhydrochloridmonohydrat, verfahren zu seiner herstellung und es enthaltendes pharmazeutisches praeparat. |
| ES198686850440T ES2036179T3 (es) | 1986-01-03 | 1986-12-15 | Procedimiento para preparar monohidrato de hidrocloruro de (s)-(-)-1-propil-2',6'-pipecoloxilidida. |
| JP61308983A JPH07598B2 (ja) | 1986-01-03 | 1986-12-26 | 光学的に純粋な化合物およびその製造方法 |
| MYPI86000260A MY101132A (en) | 1986-01-03 | 1986-12-30 | An optically pure pipecoloxylidide hydrochloride and a process for its preparation |
| CA000526453A CA1276154C (en) | 1986-01-03 | 1986-12-30 | Optically pure s-(-)-1-propyl-2,6-pipecoloxylidide hydrochloride monohydrate and a process for its preparation |
| KR1019860011720A KR940008302B1 (ko) | 1986-01-03 | 1986-12-31 | 광학적으로 순수한 s-(-)-1-프로필-2',6'-피페콜옥실리디드 염산염의 제조방법 |
| PT84041A PT84041B (pt) | 1986-01-03 | 1986-12-31 | Processo para a preparacao do cloridrato de s-(-)-1-propil-2',6'-pipecoloxilidido monohidratado opticamente puro e de composicoes farmaceuticas que o contem |
| FI870003A FI83075C (fi) | 1986-01-03 | 1987-01-02 | Foerfarande foer framstaellning av farmaceutiskt aktivt, optiskt rent monohydrat av (s)-(-)-1-propyl-2',6' -pipekoloxylididhydroklorid. |
| IE487A IE59061B1 (en) | 1986-01-03 | 1987-01-02 | An optically pure compound and a process for its preparation |
| DK000287A DK171378B1 (da) | 1986-01-03 | 1987-01-02 | S-(-)-1-propyl-2',6'-pipecoloxylididhydrochlorid-monohydrat, fremgangsmåde til fremstilling af samme og farmaceutiske præparater indeholdende forbindelsen |
| AR88306211A AR242561A1 (es) | 1986-01-03 | 1988-12-17 | Procedimiento para la preparacion de clorhidrato de s-(-)-1-propil-2',6'-pipecoloxilidida opticamente sustancialmente puro y procedimiento |
| GR90400889T GR3002516T3 (en) | 1986-01-03 | 1990-11-08 | (s)-(-)-1-propyl-2',6'-pipecoloxylidide hydrochloride monohydrate, process for its preparation and pharmaceutical preparation containing it |
| SG1172/92A SG117292G (en) | 1986-01-03 | 1992-11-06 | (s)-(-)-1-propyl-2',6'-pipecoloxylidide hydrochloride monohydrate,process for its preparation and pharmaceutical preparation containing it |
| HK54/93A HK5493A (en) | 1986-01-03 | 1993-01-21 | (s)-(-)-1-propyl-2',6'-pipecoloxylidide hydrochloride monohydrate,process for its preparation and pharmaceutical preparation containing it |
| CY1680A CY1680A (en) | 1986-01-03 | 1993-10-10 | (s)-(-)-1-propyl-2',6'-pipecoloxylidide hydrochloride monohydrate,process for its preparation and pharmaceutical preparation containing it |
| BG98494A BG62066B2 (bg) | 1986-01-03 | 1994-02-18 | (s)-(-)-1-пропил-2',6'-пипеколоксилидидов хидрохлорид монохидрат, метод за получаването му и фармацевтичен препарат, който го съдържа |
| NL960005C NL960005I2 (nl) | 1986-01-03 | 1996-03-26 | Optisch zuivere verbinding, en werkwijze voor de bereiding daarvan. |
| LV960261A LV5765B4 (lv) | 1986-01-03 | 1996-07-17 | (S)-(-)-1-propil-2',6'-pipekoloksilidida hidrohlorida monohidrats ta iegusanas metode un to satuross farmaceitisks preparats |
| LU88843C LU88843I2 (fr) | 1986-01-03 | 1996-11-27 | Ropivacaine et ses dérivés pharmaceutiquement acceptables (Naropine R) |
| NO1997009C NO1997009I1 (no) | 1986-01-03 | 1997-07-31 | Ropivacain |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8600017A SE451840B (sv) | 1986-01-03 | 1986-01-03 | Optiskt rent monohydrat av s-(-)-1-propyl-2',6'-pipekoloxylididhydroklorid, sett att framstella denna och farmaceutiska beredningar for lokalbedovning |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8600017D0 SE8600017D0 (sv) | 1986-01-03 |
| SE8600017L SE8600017L (sv) | 1987-07-04 |
| SE451840B true SE451840B (sv) | 1987-11-02 |
Family
ID=20363001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8600017A SE451840B (sv) | 1986-01-03 | 1986-01-03 | Optiskt rent monohydrat av s-(-)-1-propyl-2',6'-pipekoloxylididhydroklorid, sett att framstella denna och farmaceutiska beredningar for lokalbedovning |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4870086A (es) |
| EP (1) | EP0239710B1 (es) |
| JP (1) | JPH07598B2 (es) |
| KR (1) | KR940008302B1 (es) |
| AR (1) | AR242561A1 (es) |
| AT (1) | ATE56956T1 (es) |
| AU (1) | AU592392B2 (es) |
| BG (1) | BG62066B2 (es) |
| CA (1) | CA1276154C (es) |
| CY (1) | CY1680A (es) |
| DE (1) | DE3674582D1 (es) |
| DK (1) | DK171378B1 (es) |
| EG (1) | EG17867A (es) |
| ES (1) | ES2036179T3 (es) |
| FI (1) | FI83075C (es) |
| GR (1) | GR3002516T3 (es) |
| HK (1) | HK5493A (es) |
| IE (1) | IE59061B1 (es) |
| LU (1) | LU88843I2 (es) |
| LV (1) | LV5765B4 (es) |
| MY (1) | MY101132A (es) |
| NL (1) | NL960005I2 (es) |
| NO (2) | NO170330C (es) |
| NZ (1) | NZ218615A (es) |
| PH (1) | PH22924A (es) |
| PT (1) | PT84041B (es) |
| SE (1) | SE451840B (es) |
| SG (1) | SG117292G (es) |
| ZA (1) | ZA868600B (es) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL98392A (en) * | 1990-06-07 | 1996-01-19 | Wellcome Found | History of indole, their preparation and the pharmaceutical preparations containing them |
| ES2082703B1 (es) * | 1993-11-04 | 1996-12-16 | Inst Investigacion Desarrollo | Nuevos derivados de ciclopropilo, procedimientos para su preparacion y aplicaciones. |
| US5834490A (en) * | 1993-11-04 | 1998-11-10 | Instituto De Investigacion Y Desarrolo Quimico Biologico, S.A. | Cyclopropyl derivatives, preparation method there-of and applications |
| ES2173194T3 (es) * | 1994-09-23 | 2002-10-16 | Darwin Discovery Ltd | Procedimiento de racemizacion utilizado para la preparacion de levobupivacaina y sus analogos. |
| SE9501808D0 (sv) * | 1995-05-16 | 1995-05-16 | Astra Ab | New process |
| US7799337B2 (en) | 1997-07-21 | 2010-09-21 | Levin Bruce H | Method for directed intranasal administration of a composition |
| SE9800139D0 (sv) | 1998-01-21 | 1998-01-21 | Astra Ab | New use |
| BRPI0104491B8 (pt) * | 2001-10-10 | 2021-05-25 | Cristalia Produtos Quim Farmaceuticos Ltda | n-(2,6-dimetilfenil)-1-propil-2-piperidinocarboxamida; processo de obtenção dos enantiômeros; mistura não racêmica dos anantiômeros e seu processo de obtenção e composição farmacêutica. |
| US20060270708A1 (en) * | 2005-05-25 | 2006-11-30 | Navinta Llc | Novel process for preparation of isotonic aqueous injection of ropivacaine |
| US7683175B2 (en) * | 2005-06-06 | 2010-03-23 | Navinta, Llc | Process of making optically pure L-pipecolic acid and process of making anesthetics and intermediates therefrom |
| JP2009535327A (ja) * | 2006-04-25 | 2009-10-01 | ディシュマン・ファーマシューティカルズ・アンド・ケミカルズ・リミテッド | ロピバカイン塩酸塩無水物およびその調製 |
| EP2234974B1 (en) * | 2008-01-15 | 2012-04-25 | Pharmathen S.A. | Process for the preparation of (s)-1-alkyl-2',6'-pipecoloxylidide compound |
| US8473062B2 (en) | 2008-05-01 | 2013-06-25 | Autonomic Technologies, Inc. | Method and device for the treatment of headache |
| US8412336B2 (en) | 2008-12-29 | 2013-04-02 | Autonomic Technologies, Inc. | Integrated delivery and visualization tool for a neuromodulation system |
| US9320908B2 (en) | 2009-01-15 | 2016-04-26 | Autonomic Technologies, Inc. | Approval per use implanted neurostimulator |
| US8494641B2 (en) | 2009-04-22 | 2013-07-23 | Autonomic Technologies, Inc. | Implantable neurostimulator with integral hermetic electronic enclosure, circuit substrate, monolithic feed-through, lead assembly and anchoring mechanism |
| CN102093284B (zh) * | 2010-12-29 | 2013-05-08 | 宜昌人福药业有限责任公司 | 富集哌啶-2-甲酰苯胺类旋光化合物的方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2248018A (en) * | 1939-03-30 | 1941-07-01 | Winthrop Chem Co Inc | 4-aryl-piperidine-ketones and a process of preparing them |
| GB775749A (en) * | 1955-04-06 | 1957-05-29 | Bofors Ab | Method of preparing amides of n-alkyl piperidine monocarboxylic acid and n-alkyl pyrrolidine -a-monocarboxylic acid |
| GB775750A (en) * | 1955-04-28 | 1957-05-29 | Bofors Ab | Method of preparing amides of n-alkyl piperidine mono-carboxylic acid and n-alkyl pyrrolidine -a-monocarboxylic acid |
| US2799679A (en) * | 1955-04-28 | 1957-07-16 | Bofors Ab | Process of preparing amides of heterocyclic carboxylic acids |
| GB800565A (en) * | 1956-01-23 | 1958-08-27 | Bofors Ab | Method of producing n-alkyl-piperidine-ª‡-monocarboxylic acid amides and n-alkyl-pyrrolidine-ª‡-monocarboxylic acid amides |
| GB824542A (en) * | 1957-05-15 | 1959-12-02 | Bofors Ab | Method of producing n-alkyl-piperidine-alpha-monocarboxylic acid amides |
| GB869978A (en) * | 1958-03-13 | 1961-06-07 | Bofors Ab | Method of producing n-alkyl-and-cycloalkyl-piperidine carboxylic acid amides |
| GB949729A (en) * | 1960-11-15 | 1964-02-19 | Bofors Ab | Substituted-piperidine carboxylic acid amide salts and their preparation |
| SE341404B (es) * | 1967-05-18 | 1971-12-27 | Sterling Drug Inc | |
| CH491915A (de) * | 1967-06-28 | 1970-06-15 | Geigy Ag J R | Verfahren zur Herstellung von neuen Piperidinderivaten |
| US3879382A (en) * | 1971-08-27 | 1975-04-22 | Teijin Ltd | Process for the recovery of D- or L-{60 -amino-{68 -caprolactam hydrochloride of enhanced optical purity from mixtures of D- and L-{60 -amino-{68 -caprolactam hydrochloride |
| SE7607114L (sv) * | 1976-06-22 | 1977-12-23 | Bofors Ab | Sett att framstella hydrokloriden av n-metylpiperidin-2-karbonsyra-2,6-xyllidid |
| SE431092B (sv) * | 1979-07-10 | 1984-01-16 | Thuresson Af Ekenstam Bo | Terapeutiskt aktiva, substituerade piperidinkarboxianilider |
| EP0151110B1 (en) * | 1983-08-01 | 1989-03-01 | Astra Läkemedel Aktiebolag | L-n-n-propylpipecolic acid-2,6-xylidide and method for preparing the same |
-
1986
- 1986-01-03 SE SE8600017A patent/SE451840B/sv not_active IP Right Cessation
- 1986-11-12 ZA ZA868600A patent/ZA868600B/xx unknown
- 1986-11-24 US US06/934,114 patent/US4870086A/en not_active Expired - Lifetime
- 1986-12-02 EG EG747/86A patent/EG17867A/xx active
- 1986-12-03 NO NO864858A patent/NO170330C/no not_active IP Right Cessation
- 1986-12-12 NZ NZ218615A patent/NZ218615A/xx unknown
- 1986-12-12 AU AU66449/86A patent/AU592392B2/en not_active Expired
- 1986-12-15 ES ES198686850440T patent/ES2036179T3/es not_active Expired - Lifetime
- 1986-12-15 EP EP86850440A patent/EP0239710B1/en not_active Expired - Lifetime
- 1986-12-15 AT AT86850440T patent/ATE56956T1/de active
- 1986-12-15 DE DE8686850440T patent/DE3674582D1/de not_active Expired - Lifetime
- 1986-12-15 PH PH34593A patent/PH22924A/en unknown
- 1986-12-26 JP JP61308983A patent/JPH07598B2/ja not_active Expired - Lifetime
- 1986-12-30 MY MYPI86000260A patent/MY101132A/en unknown
- 1986-12-30 CA CA000526453A patent/CA1276154C/en not_active Expired - Lifetime
- 1986-12-31 KR KR1019860011720A patent/KR940008302B1/ko not_active IP Right Cessation
- 1986-12-31 PT PT84041A patent/PT84041B/pt unknown
-
1987
- 1987-01-02 DK DK000287A patent/DK171378B1/da not_active IP Right Cessation
- 1987-01-02 FI FI870003A patent/FI83075C/fi not_active IP Right Cessation
- 1987-01-02 IE IE487A patent/IE59061B1/en not_active IP Right Cessation
-
1988
- 1988-12-17 AR AR88306211A patent/AR242561A1/es active
-
1990
- 1990-11-08 GR GR90400889T patent/GR3002516T3/el unknown
-
1992
- 1992-11-06 SG SG1172/92A patent/SG117292G/en unknown
-
1993
- 1993-01-21 HK HK54/93A patent/HK5493A/xx not_active IP Right Cessation
- 1993-10-10 CY CY1680A patent/CY1680A/xx unknown
-
1994
- 1994-02-18 BG BG98494A patent/BG62066B2/bg unknown
-
1996
- 1996-03-26 NL NL960005C patent/NL960005I2/nl unknown
- 1996-07-17 LV LV960261A patent/LV5765B4/xx unknown
- 1996-11-27 LU LU88843C patent/LU88843I2/fr unknown
-
1997
- 1997-07-31 NO NO1997009C patent/NO1997009I1/no unknown
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