ES8603442A1 - Procedimiento para la obtencion de derivados piperazinicos - Google Patents
Procedimiento para la obtencion de derivados piperazinicosInfo
- Publication number
- ES8603442A1 ES8603442A1 ES542946A ES542946A ES8603442A1 ES 8603442 A1 ES8603442 A1 ES 8603442A1 ES 542946 A ES542946 A ES 542946A ES 542946 A ES542946 A ES 542946A ES 8603442 A1 ES8603442 A1 ES 8603442A1
- Authority
- ES
- Spain
- Prior art keywords
- opt
- alkyl
- substd
- aryl
- unsatd
- 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
- 230000001078 anti-cholinergic effect Effects 0.000 title 1
- 230000001387 anti-histamine Effects 0.000 title 1
- 150000004885 piperazines Chemical class 0.000 title 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 6
- 125000003118 aryl group Chemical group 0.000 abstract 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 3
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 150000001450 anions Chemical group 0.000 abstract 2
- 230000000648 anti-parkinson Effects 0.000 abstract 2
- 239000000939 antiparkinson agent Substances 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 230000001588 bifunctional effect Effects 0.000 abstract 2
- 239000000812 cholinergic antagonist Substances 0.000 abstract 2
- 230000000694 effects Effects 0.000 abstract 2
- 230000002496 gastric effect Effects 0.000 abstract 2
- 210000001035 gastrointestinal tract Anatomy 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 210000003734 kidney Anatomy 0.000 abstract 2
- 230000002911 mydriatic effect Effects 0.000 abstract 2
- 150000007524 organic acids Chemical class 0.000 abstract 2
- 230000028327 secretion Effects 0.000 abstract 2
- 230000002048 spasmolytic effect Effects 0.000 abstract 2
- 210000003932 urinary bladder Anatomy 0.000 abstract 2
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 239000000739 antihistaminic agent Substances 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 201000003152 motion sickness Diseases 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- 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]
-
- 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom 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)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Anesthesiology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
PROCEDIMIENTO PARA LA OBTENCION DE DERIVADOS PIPERAZINICOS, ASI COMO DE SUS ENANTIOMEROS Y DIASTEREOISOMEROS, DE FORMULA (I), EN LA QUE Y, A, R, R1, R2, R3 Y R4 PUEDEN SER VARIOS TIPOS DE RADICALES; X REPRESENTA HALOGENO O EL ANION DE UN ACIDO; Y N VALE 0-3. CONSISTE EN LA REDUCCION DEL GRUPO CARBONILO A GRUPO CH2 EN UNA AMIDA DE FORMULA (II), EN LA QUE TODOS LOS SIMBOLOS TIENEN EL MISMO SIGNIFICADO QUE EN LA FORMULA (I). LA REDUCCION SE LLEVA A CABO CON UN HIDRURO METALICO, TAL COMO HIDRURO DE LITIO Y ALUMINIO, EN UN DISOLVENTE INERTE, TAL COMO TETRAHIDROFURANO, A LA TEMPERATURA AMBIENTE. ESTOS COMPUESTOS TIENEN APLICACIONES FARMACOLOGICAS POR SUS EFECTOS ESPASMOLITICOS ANTICOLINERGICOS.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/424,512 US4457931A (en) | 1982-09-27 | 1982-09-27 | Piperazine derivatives with anticholinergic and/or antihistaminic activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES542946A0 ES542946A0 (es) | 1986-01-01 |
| ES8603442A1 true ES8603442A1 (es) | 1986-01-01 |
Family
ID=23682887
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES525953A Expired ES8604543A1 (es) | 1982-09-27 | 1983-09-26 | Procedimiento para la obtencion de derivados piperazinicos |
| ES542947A Granted ES542947A0 (es) | 1982-09-27 | 1985-04-16 | Procedimiento para la obtencion de derivados piperazinicos |
| ES542946A Expired ES8603442A1 (es) | 1982-09-27 | 1985-04-16 | Procedimiento para la obtencion de derivados piperazinicos |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES525953A Expired ES8604543A1 (es) | 1982-09-27 | 1983-09-26 | Procedimiento para la obtencion de derivados piperazinicos |
| ES542947A Granted ES542947A0 (es) | 1982-09-27 | 1985-04-16 | Procedimiento para la obtencion de derivados piperazinicos |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4457931A (es) |
| JP (1) | JPS5989665A (es) |
| BE (1) | BE897828A (es) |
| DE (1) | DE3334757A1 (es) |
| ES (3) | ES8604543A1 (es) |
| FR (1) | FR2533564B1 (es) |
| GB (1) | GB2135991B (es) |
| IT (1) | IT1212088B (es) |
| NL (1) | NL8303311A (es) |
| ZA (1) | ZA836949B (es) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6147466A (ja) * | 1984-08-10 | 1986-03-07 | Dainippon Pharmaceut Co Ltd | アミン誘導体 |
| FR2573075B1 (fr) * | 1984-09-14 | 1987-03-20 | Innothera Lab Sa | Nouvelles (pyridyl-2)-1 piperazines, leur procede de preparation et leur application en therapeutique |
| EP0350145A3 (en) * | 1988-04-28 | 1990-07-04 | Yamanouchi Pharmaceutical Co. Ltd. | Pyridylthiazolidine carboxamide derivatives and their intermediates and production of both |
| GB2227018B (en) * | 1989-01-13 | 1992-05-20 | Wyeth John & Brother Ltd | Piperazinylalkylcarboxylic acid adamantylamides |
| JPH05255089A (ja) * | 1991-12-18 | 1993-10-05 | Sanwa Kagaku Kenkyusho Co Ltd | 抗ウイルス剤 |
| SE9201956D0 (sv) * | 1992-06-25 | 1992-06-25 | Kabi Pharmacia Ab | Novel nicotinicacid esters |
| GB9817197D0 (en) * | 1998-08-07 | 1998-10-07 | Lilly Co Eli | Pharmaceutical compounds |
| EP1421071B1 (en) * | 2001-07-02 | 2009-11-18 | High Point Pharmaceuticals, LLC | Substituted piperazine and diazepane derivaives as histamine h3 receptor modulators |
| US20040033986A1 (en) * | 2002-05-17 | 2004-02-19 | Protopopova Marina Nikolaevna | Anti tubercular drug: compositions and methods |
| US7456222B2 (en) * | 2002-05-17 | 2008-11-25 | Sequella, Inc. | Anti tubercular drug: compositions and methods |
| CN101404986B (zh) * | 2002-05-17 | 2011-09-28 | 赛奎拉公司 | 用于诊断和治疗感染性疾病的组合物和制药方法 |
| EP1644347A1 (en) * | 2003-06-20 | 2006-04-12 | Arena Pharmaceuticals, Inc. | N-PHENYL-PIPERAZINE DERIVATIVES AND METHODS OF PROPHYLAXIS OR TREATMENT OF 5HT sb 2C /sb RECEPTOR ASSOCIATED DISEASES |
| EP1670314A4 (en) * | 2003-09-05 | 2009-02-25 | Sequella Inc | METHODS AND COMPOSITIONS INCLUDE DIAMINE AS A NEW THERAPEUTIC FOR TUBERCULOSIS |
| CA2594987A1 (en) * | 2004-12-14 | 2006-06-22 | Shionogi & Co., Ltd. | Therapeutic agent for constipation |
| US20090281054A1 (en) * | 2008-05-06 | 2009-11-12 | Venkata Reddy | Compositions and methods comprising capuramycin analogues |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR997607A (fr) * | 1949-10-14 | 1952-01-08 | American Cyanamid Co | Perfectionnements relatifs aux pipérazines substituées |
| US2794804A (en) * | 1955-03-24 | 1957-06-04 | American Cyanamid Co | Substituted piperazines and method of preparing the same |
| BE637271A (es) * | 1963-04-04 | 1900-01-01 | ||
| US3712893A (en) * | 1969-11-10 | 1973-01-23 | Cerm Cent Europ Rech Mauvernay | Butyl-piperazine derivatives |
| JPS49101383A (es) * | 1973-02-05 | 1974-09-25 | ||
| JPS517673A (ja) * | 1974-07-08 | 1976-01-22 | Hitachi Ltd | Hansoshisutemu |
| JPS5111635A (es) * | 1974-07-18 | 1976-01-29 | Hideji Kitamura | |
| FR2306694A1 (fr) * | 1975-04-07 | 1976-11-05 | Parcor | Derives de la piperazine |
| JPS523387A (en) * | 1975-06-24 | 1977-01-11 | Nec Home Electronics Ltd | Manufacturing method of semiconductor device |
| JPS54103893A (en) * | 1978-01-26 | 1979-08-15 | Morishita Pharma | 1*44benzodioxane derivative |
| AU532411B2 (en) * | 1979-03-01 | 1983-09-29 | Duphar International Research B.V. | Phenyl piperazine derivatives |
| JPS5827793B2 (ja) * | 1980-09-18 | 1983-06-11 | 住友化学工業株式会社 | 新規なアニリン誘導体の製法 |
| JPS5761149A (en) * | 1980-09-30 | 1982-04-13 | Matsushita Electric Works Ltd | Staircase |
-
1982
- 1982-09-27 US US06/424,512 patent/US4457931A/en not_active Expired - Fee Related
-
1983
- 1983-09-06 IT IT8322784A patent/IT1212088B/it active
- 1983-09-19 ZA ZA836949A patent/ZA836949B/xx unknown
- 1983-09-22 JP JP58176190A patent/JPS5989665A/ja active Granted
- 1983-09-23 FR FR8315172A patent/FR2533564B1/fr not_active Expired
- 1983-09-26 ES ES525953A patent/ES8604543A1/es not_active Expired
- 1983-09-26 DE DE19833334757 patent/DE3334757A1/de not_active Withdrawn
- 1983-09-27 BE BE2/60212A patent/BE897828A/nl not_active IP Right Cessation
- 1983-09-27 GB GB08325839A patent/GB2135991B/en not_active Expired
- 1983-09-27 NL NL8303311A patent/NL8303311A/nl not_active Application Discontinuation
-
1985
- 1985-04-16 ES ES542947A patent/ES542947A0/es active Granted
- 1985-04-16 ES ES542946A patent/ES8603442A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES8604543A1 (es) | 1986-02-01 |
| FR2533564A1 (fr) | 1984-03-30 |
| ZA836949B (en) | 1984-05-30 |
| ES525953A0 (es) | 1986-02-01 |
| ES8603443A1 (es) | 1986-01-01 |
| DE3334757A1 (de) | 1984-03-29 |
| GB2135991B (en) | 1985-12-04 |
| IT1212088B (it) | 1989-11-08 |
| ES542947A0 (es) | 1986-01-01 |
| BE897828A (nl) | 1984-01-16 |
| FR2533564B1 (fr) | 1986-10-03 |
| ES542946A0 (es) | 1986-01-01 |
| GB8325839D0 (en) | 1983-10-26 |
| JPS6139289B2 (es) | 1986-09-03 |
| NL8303311A (nl) | 1984-04-16 |
| GB2135991A (en) | 1984-09-12 |
| IT8322784A0 (it) | 1983-09-06 |
| US4457931A (en) | 1984-07-03 |
| JPS5989665A (ja) | 1984-05-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |
Effective date: 19960401 |