GB1386146A - Cyclopentane derivatives - Google Patents
Cyclopentane derivativesInfo
- Publication number
- GB1386146A GB1386146A GB2056672A GB2056672A GB1386146A GB 1386146 A GB1386146 A GB 1386146A GB 2056672 A GB2056672 A GB 2056672A GB 2056672 A GB2056672 A GB 2056672A GB 1386146 A GB1386146 A GB 1386146A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compounds
- cyclopenta
- hexahydro
- furan
- 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
- 125000001511 cyclopentyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 14
- -1 thienyl radical Chemical class 0.000 abstract 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 3
- 150000003180 prostaglandins Chemical class 0.000 abstract 3
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 abstract 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- LMKPHJYTFHAGHK-UHFFFAOYSA-N cyclodrine Chemical compound C1CCCC1(O)C(C(=O)OCCN(CC)CC)C1=CC=CC=C1 LMKPHJYTFHAGHK-UHFFFAOYSA-N 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 1
- CPVNCBJFUQQXSU-UHFFFAOYSA-N 5-triphenylphosphaniumylpentanoate Chemical class C1(=CC=CC=C1)[P+](CCCCC(=O)[O-])(C1=CC=CC=C1)C1=CC=CC=C1 CPVNCBJFUQQXSU-UHFFFAOYSA-N 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000004183 alkoxy alkyl 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
- 239000000969 carrier Substances 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000005059 halophenyl group Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000001802 infusion Methods 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 150000002596 lactones Chemical class 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical class [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 238000005507 spraying Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07C405/0016—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing only hydroxy, etherified or esterified hydroxy groups
-
- 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
- C07C405/0025—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing keto groups
-
- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings 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
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- 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
- C07F9/4056—Esters of arylalkanephosphonic acids
- C07F9/4059—Compounds containing the structure (RY)2P(=X)-(CH2)n-C(=O)-(CH2)m-Ar, (X, Y = O, S, Se; n>=1, m>=0)
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2056672A GB1386146A (en) | 1972-05-03 | 1972-05-03 | Cyclopentane derivatives |
| ZA732585A ZA732585B (en) | 1972-05-03 | 1973-04-13 | Cyclopentane derivatives |
| NL7306030A NL7306030A (US07122603-20061017-C00045.png) | 1972-05-03 | 1973-05-01 | |
| JP48049611A JPS5740142B2 (US07122603-20061017-C00045.png) | 1972-05-03 | 1973-05-02 | |
| DE2322142A DE2322142C2 (de) | 1972-05-03 | 1973-05-02 | Prostansäurederivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische oder veterinäre Zuammensetzungen |
| FR7315738A FR2269331B1 (US07122603-20061017-C00045.png) | 1972-05-03 | 1973-05-02 | |
| CA170,207A CA1042002A (en) | 1972-05-03 | 1973-05-02 | Cyclopentane derivatives |
| ES414343A ES414343A1 (es) | 1972-05-03 | 1973-05-03 | Procedimiento para la obtencion de derivados del acido prostanoico. |
| BE130703A BE799048A (fr) | 1972-05-03 | 1973-05-03 | Derives du cyclopentane |
| CH391776A CH594621A5 (US07122603-20061017-C00045.png) | 1972-05-03 | 1973-05-03 | |
| CH391876A CH594622A5 (US07122603-20061017-C00045.png) | 1972-05-03 | 1973-05-03 | |
| CH631773A CH581617A5 (US07122603-20061017-C00045.png) | 1972-05-03 | 1973-05-03 | |
| SE7603276A SE7603276L (sv) | 1972-05-03 | 1976-03-15 | Sett att framstella prostansyraderivat |
| SE7603277A SE7603277L (sv) | 1972-05-03 | 1976-03-15 | Sett att framstella prostansyraderivat |
| JP56137136A JPS5825670B2 (ja) | 1972-05-03 | 1981-09-02 | プロスタン酸誘導体の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2056672A GB1386146A (en) | 1972-05-03 | 1972-05-03 | Cyclopentane derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1386146A true GB1386146A (en) | 1975-03-05 |
Family
ID=10148032
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2056672A Expired GB1386146A (en) | 1972-05-03 | 1972-05-03 | Cyclopentane derivatives |
Country Status (11)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES416865A1 (es) * | 1972-07-13 | 1976-03-01 | Pfizer | Procedimiento para preparar w-pentanorprostaglandinas sus- tituidas en la posicion 15. |
| US4113723A (en) | 1972-07-13 | 1978-09-12 | Pfizer Inc. | 15-Substituted-ω-pentanorprostaglandins |
| GB1432950A (en) * | 1972-11-10 | 1976-04-22 | Ici Ltd | Cyclopentane aldehydes as chemical intermediates |
| GB1431561A (en) * | 1973-01-31 | 1976-04-07 | Ici Ltd | Cyclopentane derivatives |
| SE423813B (sv) * | 1976-08-06 | 1982-06-07 | Pfizer | Forfarande for framstellning av 1,5-disubstituerade pyrrolidoner med terapeutiska egenskaper |
| US4149006A (en) * | 1977-01-24 | 1979-04-10 | G. D. Searle & Co. | Prostaglandin derivatives having alkynyl, hydroxy and aryloxy junctions in the 2β side chain |
| GB8329559D0 (en) * | 1983-11-04 | 1983-12-07 | Erba Farmitalia | Furyl derivatives of 16-substituted prostaglandins preparations |
| US4784374A (en) * | 1987-05-14 | 1988-11-15 | Union Carbide Corporation | Two-stage aluminum refining vessel |
| BR0008776A (pt) * | 1999-03-05 | 2001-12-18 | Procter & Gamble | Análogos de prostaglandinas fp-seletivosinsaturados c16 |
| US20020013294A1 (en) | 2000-03-31 | 2002-01-31 | Delong Mitchell Anthony | Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES416865A1 (es) * | 1972-07-13 | 1976-03-01 | Pfizer | Procedimiento para preparar w-pentanorprostaglandinas sus- tituidas en la posicion 15. |
-
1972
- 1972-05-03 GB GB2056672A patent/GB1386146A/en not_active Expired
-
1973
- 1973-04-13 ZA ZA732585A patent/ZA732585B/xx unknown
- 1973-05-01 NL NL7306030A patent/NL7306030A/xx not_active Application Discontinuation
- 1973-05-02 CA CA170,207A patent/CA1042002A/en not_active Expired
- 1973-05-02 JP JP48049611A patent/JPS5740142B2/ja not_active Expired
- 1973-05-02 DE DE2322142A patent/DE2322142C2/de not_active Expired
- 1973-05-02 FR FR7315738A patent/FR2269331B1/fr not_active Expired
- 1973-05-03 CH CH391776A patent/CH594621A5/xx not_active IP Right Cessation
- 1973-05-03 BE BE130703A patent/BE799048A/xx unknown
- 1973-05-03 CH CH391876A patent/CH594622A5/xx not_active IP Right Cessation
- 1973-05-03 CH CH631773A patent/CH581617A5/xx not_active IP Right Cessation
- 1973-05-03 ES ES414343A patent/ES414343A1/es not_active Expired
-
1976
- 1976-03-15 SE SE7603276A patent/SE7603276L/xx unknown
- 1976-03-15 SE SE7603277A patent/SE7603277L/xx unknown
-
1981
- 1981-09-02 JP JP56137136A patent/JPS5825670B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2269331A1 (US07122603-20061017-C00045.png) | 1975-11-28 |
| SE7603277L (sv) | 1976-03-15 |
| DE2322142A1 (de) | 1973-11-22 |
| ZA732585B (en) | 1974-03-27 |
| BE799048A (fr) | 1973-11-05 |
| SE7603276L (sv) | 1976-03-15 |
| JPS5825670B2 (ja) | 1983-05-28 |
| CA1042002A (en) | 1978-11-07 |
| FR2269331B1 (US07122603-20061017-C00045.png) | 1978-07-07 |
| ES414343A1 (es) | 1976-06-16 |
| JPS4975558A (US07122603-20061017-C00045.png) | 1974-07-20 |
| CH594621A5 (US07122603-20061017-C00045.png) | 1978-01-13 |
| JPS5740142B2 (US07122603-20061017-C00045.png) | 1982-08-25 |
| CH594622A5 (US07122603-20061017-C00045.png) | 1978-01-13 |
| DE2322142C2 (de) | 1982-07-01 |
| NL7306030A (US07122603-20061017-C00045.png) | 1973-11-06 |
| CH581617A5 (US07122603-20061017-C00045.png) | 1976-11-15 |
| JPS57158757A (en) | 1982-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |