JPS57176960A - Azaprostacycline, manufacture and medicine containing same - Google Patents
Azaprostacycline, manufacture and medicine containing sameInfo
- Publication number
- JPS57176960A JPS57176960A JP57023695A JP2369582A JPS57176960A JP S57176960 A JPS57176960 A JP S57176960A JP 57023695 A JP57023695 A JP 57023695A JP 2369582 A JP2369582 A JP 2369582A JP S57176960 A JPS57176960 A JP S57176960A
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- hydrogen
- alkyl
- independently
- alkylene
- 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.)
- Granted
Links
- 239000003814 drug Substances 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 9
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract 8
- 239000001257 hydrogen Substances 0.000 abstract 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 230000003182 bronchodilatating effect Effects 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- -1 phenacyl residue Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
-
- 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
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0041—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/13—Dicarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/26—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4015—Esters of acyclic unsaturated acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4018—Esters of cycloaliphatic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biochemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Hematology (AREA)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Steroid Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813107100 DE3107100A1 (de) | 1981-02-20 | 1981-02-20 | Azaprostacycline, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57176960A true JPS57176960A (en) | 1982-10-30 |
| JPH0245622B2 JPH0245622B2 (cg-RX-API-DMAC10.html) | 1990-10-11 |
Family
ID=6125738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57023695A Granted JPS57176960A (en) | 1981-02-20 | 1982-02-18 | Azaprostacycline, manufacture and medicine containing same |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US4446147A (cg-RX-API-DMAC10.html) |
| EP (1) | EP0059158B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JPS57176960A (cg-RX-API-DMAC10.html) |
| AT (1) | ATE36152T1 (cg-RX-API-DMAC10.html) |
| AU (1) | AU8038882A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1205468A (cg-RX-API-DMAC10.html) |
| CS (1) | CS228916B2 (cg-RX-API-DMAC10.html) |
| DE (2) | DE3107100A1 (cg-RX-API-DMAC10.html) |
| DK (1) | DK72782A (cg-RX-API-DMAC10.html) |
| ES (1) | ES8301914A1 (cg-RX-API-DMAC10.html) |
| HU (1) | HU187649B (cg-RX-API-DMAC10.html) |
| IE (1) | IE54097B1 (cg-RX-API-DMAC10.html) |
| IL (1) | IL65055A0 (cg-RX-API-DMAC10.html) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL76612A (en) * | 1984-10-09 | 1990-01-18 | Syntex Inc | Intermediates for preparing 16-phenoxy-prostatrienoic acid derivatives and their preparation |
| US6982251B2 (en) * | 2000-12-20 | 2006-01-03 | Schering Corporation | Substituted 2-azetidinones useful as hypocholesterolemic agents |
| IL156585A0 (en) * | 2001-01-26 | 2004-01-04 | Schering Corp | Combinations of sterol absorption inhibitor(s) with cardiovascular agent(s) for the treatment of vascular conditions |
| MXPA03006727A (es) * | 2001-01-26 | 2003-10-24 | Schering Corp | Combinaciones de acido nicotinico y derivados del mismo con inhibidor(es) de la absorcion de los esteroles, y tratamiento para indicaciones vasculares. |
| EP1363668B1 (en) * | 2001-01-26 | 2007-08-15 | Schering Corporation | Combinations of bile acid sequestrant(s) and sterol absorption inhibitor(s) and treatments for vascular indications |
| MEP27808A (en) * | 2001-01-26 | 2010-10-10 | Schering Corp | Combinations of peroxisome proliferator-activated receptor (ppar) activator(s) and sterol absorption inhibitor(s) and treatments for vascular indications |
| US20060287254A1 (en) * | 2001-01-26 | 2006-12-21 | Schering Corporation | Use of substituted azetidinone compounds for the treatment of sitosterolemia |
| JP2004517920A (ja) * | 2001-01-26 | 2004-06-17 | シェーリング コーポレイション | 血管状態を治療するためのステロール吸収阻害剤と血液調整剤との組合せ |
| US7071181B2 (en) * | 2001-01-26 | 2006-07-04 | Schering Corporation | Methods and therapeutic combinations for the treatment of diabetes using sterol absorption inhibitors |
| ATE331512T1 (de) * | 2001-01-26 | 2006-07-15 | Schering Corp | Verwendung azetidinone-substituierter verbindungen zur behandlung der sitosterolhämie |
| AR038956A1 (es) * | 2001-05-25 | 2005-02-02 | Schering Corp | Uso de un compuesto que regula la produccion o niveles de peptidos beta amiloides para la manufactura de un medicamento para tratar la enfermedad de alzheimer y/o para regular dichos niveles de peptidos amiloides beta en un sujeto |
| ES2312624T3 (es) * | 2001-09-21 | 2009-03-01 | Schering Corporation | Metodos para tratar o prevenir la inflamacion vascular usando un inhibidor (inhibidores) de la absorcion de esterol. |
| JP2005504091A (ja) * | 2001-09-21 | 2005-02-10 | シェーリング コーポレイション | ステロール吸収阻害剤としてアゼチジノンを用いる黄色腫の処置 |
| US20030119808A1 (en) * | 2001-09-21 | 2003-06-26 | Schering Corporation | Methods of treating or preventing cardiovascular conditions while preventing or minimizing muscular degeneration side effects |
| US7053080B2 (en) * | 2001-09-21 | 2006-05-30 | Schering Corporation | Methods and therapeutic combinations for the treatment of obesity using sterol absorption inhibitors |
| US7056906B2 (en) * | 2001-09-21 | 2006-06-06 | Schering Corporation | Combinations of hormone replacement therapy composition(s) and sterol absorption inhibitor(s) and treatments for vascular conditions in post-menopausal women |
| WO2004043457A1 (en) * | 2002-11-06 | 2004-05-27 | Schering Corporation | Cholesterol absorptions inhibitors for the treatment of autoimmune disorders |
| CA2517571C (en) * | 2003-03-07 | 2011-07-05 | Schering Corporation | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof |
| MXPA05009501A (es) | 2003-03-07 | 2005-10-18 | Schering Corp | Compuestos de azetidinona sustituidos, formulaciones y usos de los mismos para el tratamiento de hipercolesterolemia. |
| EP1606287B1 (en) * | 2003-03-07 | 2013-10-02 | Merck Sharp & Dohme Corp. | Substituted azetidinone compounds, formulations and uses thereof for the treatment of hypercholesterolemia |
| US7459442B2 (en) * | 2003-03-07 | 2008-12-02 | Schering Corporation | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof |
| WO2005046797A2 (en) * | 2003-11-05 | 2005-05-26 | Schering Corporation | Combinations of lipid modulating agents and substituted azetidinones and treatments for vascular conditions |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| EP2170930B3 (en) | 2007-06-04 | 2013-10-02 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| JP2011522828A (ja) | 2008-06-04 | 2011-08-04 | シナジー ファーマシューティカルズ インコーポレイテッド | 胃腸障害、炎症、癌、およびその他の障害の治療のために有用なグアニル酸シクラーゼのアゴニスト |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| CA2905435A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| US9708367B2 (en) | 2013-03-15 | 2017-07-18 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase and their uses |
| RS65632B1 (sr) | 2013-06-05 | 2024-07-31 | Bausch Health Ireland Ltd | Ultra-prečišćeni agonisti guanilat-ciklaze c, postupak njihove pripreme i upotrebe |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2940746A1 (de) * | 1978-10-13 | 1980-04-24 | Upjohn Co | Prostacycline |
| DE2907118A1 (de) * | 1979-02-20 | 1980-09-04 | Schering Ag | Neue prostacyclin-derivate und verfahren zu ihrer herstellung |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4097489A (en) * | 1977-06-17 | 1978-06-27 | The Upjohn Company | 9-Deoxy-9α,6-nitrilo or 6,9α-imino-PGF compounds |
| DE2734791A1 (de) * | 1977-07-29 | 1979-02-15 | Schering Ag | Neue prostaglandin-i tief 2 -derivate und verfahren zu ihrer herstellung |
| DE2902809A1 (de) * | 1979-01-25 | 1980-08-07 | Hoechst Ag | Neue analoga von prostacyclin |
| US4496742A (en) * | 1981-10-13 | 1985-01-29 | The Upjohn Company | Analogs of 5,6-dihydro PGI2 |
-
1981
- 1981-02-20 DE DE19813107100 patent/DE3107100A1/de not_active Ceased
-
1982
- 1982-02-11 AU AU80388/82A patent/AU8038882A/en not_active Abandoned
- 1982-02-18 JP JP57023695A patent/JPS57176960A/ja active Granted
- 1982-02-19 IL IL65055A patent/IL65055A0/xx unknown
- 1982-02-19 DK DK72782A patent/DK72782A/da not_active Application Discontinuation
- 1982-02-19 CS CS821172A patent/CS228916B2/cs unknown
- 1982-02-19 HU HU82519A patent/HU187649B/hu not_active IP Right Cessation
- 1982-02-19 ES ES509738A patent/ES8301914A1/es not_active Expired
- 1982-02-19 CA CA000396656A patent/CA1205468A/en not_active Expired
- 1982-02-19 EP EP82730015A patent/EP0059158B1/de not_active Expired
- 1982-02-19 AT AT82730015T patent/ATE36152T1/de not_active IP Right Cessation
- 1982-02-19 DE DE8282730015T patent/DE3278854D1/de not_active Expired
- 1982-02-22 IE IE355/82A patent/IE54097B1/en unknown
- 1982-02-22 US US06/350,674 patent/US4446147A/en not_active Expired - Fee Related
-
1984
- 1984-03-21 US US06/591,719 patent/US4567195A/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2940746A1 (de) * | 1978-10-13 | 1980-04-24 | Upjohn Co | Prostacycline |
| DE2907118A1 (de) * | 1979-02-20 | 1980-09-04 | Schering Ag | Neue prostacyclin-derivate und verfahren zu ihrer herstellung |
Also Published As
| Publication number | Publication date |
|---|---|
| US4446147A (en) | 1984-05-01 |
| ATE36152T1 (de) | 1988-08-15 |
| IE54097B1 (en) | 1989-06-21 |
| EP0059158A2 (de) | 1982-09-01 |
| AU8038882A (en) | 1982-08-26 |
| IL65055A0 (en) | 1982-04-30 |
| DE3107100A1 (de) | 1982-09-09 |
| EP0059158A3 (en) | 1983-03-09 |
| ES509738A0 (es) | 1983-02-01 |
| CS228916B2 (en) | 1984-05-14 |
| DK72782A (da) | 1982-08-21 |
| EP0059158B1 (de) | 1988-08-03 |
| ES8301914A1 (es) | 1983-02-01 |
| DE3278854D1 (en) | 1988-09-08 |
| HU187649B (en) | 1986-02-28 |
| IE820355L (en) | 1982-08-20 |
| CA1205468A (en) | 1986-06-03 |
| JPH0245622B2 (cg-RX-API-DMAC10.html) | 1990-10-11 |
| US4567195A (en) | 1986-01-28 |
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