GB1508168A - 11-deoxy-15-substituted-16,17,18,19,20-pentanorprostaglandins - Google Patents

11-deoxy-15-substituted-16,17,18,19,20-pentanorprostaglandins

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Publication number
GB1508168A
GB1508168A GB50700/75A GB5070075A GB1508168A GB 1508168 A GB1508168 A GB 1508168A GB 50700/75 A GB50700/75 A GB 50700/75A GB 5070075 A GB5070075 A GB 5070075A GB 1508168 A GB1508168 A GB 1508168A
Authority
GB
United Kingdom
Prior art keywords
alkyl
phenyl
thienyl
naphthyl
alkoxy
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
Application number
GB50700/75A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pfizer Inc
Original Assignee
Pfizer Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Pfizer Inc filed Critical Pfizer Inc
Publication of GB1508168A publication Critical patent/GB1508168A/en
Expired legal-status Critical Current

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    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • 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
    • C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/06—Saturated compounds having a carboxyl group bound to a five-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • 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
    • 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
    • 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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1896—Compounds having one or more Si-O-acyl linkages
    • 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)

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Emergency Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Furan Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyrane Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1508168 11-Deoxyprostaglandins PFIZER Inc 10 Dec 1975 [11 Dec 1974] 50700/75 Heading C2C The invention comprises 11-deoxy-16,17,18,- 19,20-prostaglandins of the E or F series or 15- epimers thereof having at the 15-position a hydroxyl or oxo group and one substituent of the formula wherein R is H or CH 3 and Ar is 1- or 2-thienyl, 5 - phenyl - 1 - or 2 - thienyl, 5 - (C 1-6 alkyl)- 1- or 2-thienyl, 1- or 2-naphthyl, tropanyl, 3,4-dimethoxyphenyl, 3,4-methylenedioxyphenyl, 3,4-diohlorophenyl, 3,5-dimethylphenyl or phenyl optionally mono-substituted by Cl, Br, F, CF 3 , C 1-6 alkyl, C 1-6 alkoxy or phenyl; pharmaceutically acceptable salts thereof; C 1 esters thereof, wherein the esterifying group is C 1-10 alkyl, C 7-10 aralkyl, 1- or 2-naphthyl, or phenyl optionally substituted by Cl, Br, F, C 1-6 alkyl, C 1-6 alkoxy or phenyl; compounds in which the C 15 and/or C 9 hydroxy groups are esterified; and 11-deoxyprostaglandins of the formula wherein R<SP>1</SP> is H, C 1-10 alkyl, C 7-9 aralkyl, 1- or 2- naphthyl, or phenyl optionally substituted by Cl, Br, F, C 1-6 alkyl, C 1-6 alkoxy or phenyl, W is a single or cis-double bond, Z is a single or transdouble bond; R 1 is 2-tetrahydropyranyl and M is oxo or where R 4 is free or esterified hydroxy group. The compounds are prepared by standard methods. Pharmaceutical compositions, suitable for parenteral, oral, intravaginal, intranasal and topical administration, contain the above prostaglandins or salts or esters thereof in admixture with pharmaceutically acceptable carriers. The compounds possess similar pharmacological properties to those of the naturally occurring prostaglandins.
GB50700/75A 1974-12-11 1975-12-10 11-deoxy-15-substituted-16,17,18,19,20-pentanorprostaglandins Expired GB1508168A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US53167674A 1974-12-11 1974-12-11

Publications (1)

Publication Number Publication Date
GB1508168A true GB1508168A (en) 1978-04-19

Family

ID=24118594

Family Applications (3)

Application Number Title Priority Date Filing Date
GB50700/75A Expired GB1508168A (en) 1974-12-11 1975-12-10 11-deoxy-15-substituted-16,17,18,19,20-pentanorprostaglandins
GB29061/77A Expired GB1508170A (en) 1974-12-11 1975-12-10 Substituted cyclopentane compounds useful as intermediates in the synthesis of prostaglandin analogues
GB29060/77A Expired GB1508169A (en) 1974-12-11 1975-12-10 Substituted cyclopenta(b)furan compounds useful in the synthesis of prostaglandin analogues

Family Applications After (2)

Application Number Title Priority Date Filing Date
GB29061/77A Expired GB1508170A (en) 1974-12-11 1975-12-10 Substituted cyclopentane compounds useful as intermediates in the synthesis of prostaglandin analogues
GB29060/77A Expired GB1508169A (en) 1974-12-11 1975-12-10 Substituted cyclopenta(b)furan compounds useful in the synthesis of prostaglandin analogues

Country Status (21)

Country Link
JP (3) JPS51125257A (en)
AT (1) AT351185B (en)
BE (1) BE836564A (en)
CH (1) CH610302A5 (en)
CS (3) CS194745B2 (en)
DD (3) DD129649A5 (en)
DE (1) DE2555210A1 (en)
DK (1) DK559975A (en)
ES (1) ES443421A1 (en)
FI (1) FI753475A (en)
FR (1) FR2293923A1 (en)
GB (3) GB1508168A (en)
GR (1) GR60310B (en)
IE (1) IE43815B1 (en)
IL (2) IL48617A0 (en)
LU (1) LU73997A1 (en)
NL (1) NL166015C (en)
NO (1) NO754195L (en)
NZ (1) NZ179502A (en)
SE (1) SE7513602L (en)
ZA (1) ZA747723B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6586468B1 (en) 1998-09-14 2003-07-01 Ono Pharmaceutical Co., Ltd. ω-substituted phenyl-prostaglandin E derivatives and drugs containing the same as the active ingredient

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5486540A (en) * 1993-10-28 1996-01-23 Allergan, Inc. Cyclopentane heptanoic or heptenoic acid, 2-arylalkyl or arylalkenyl and derivatives as therapeutic agents
US9284274B2 (en) 2005-12-07 2016-03-15 Ramot At Tel-Aviv University Ltd. Chemical derivatives of jasmonate, pharmaceutical compositions and methods of use thereof
WO2007066336A2 (en) * 2005-12-07 2007-06-14 Ramot At Tel Aviv University Ltd. Chemical derivatives of jasmonate, pharmaceutical compositions and methods of use thereof
US9284252B2 (en) 2009-06-09 2016-03-15 Sepal Pharma Ltd. Use of jasmonate ester derivatives for treating benign hyperproliferative skin disorders
EP2874620B1 (en) * 2012-07-19 2016-10-12 Cayman Chemical Company, Incorporated Difluorolactam compositions for ep4-mediated osteo related diseases and conditions

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NO143741C (en) * 1972-07-13 1981-04-08 Pfizer ANALOGY PROCEDURE FOR THE PREPARATION OF PHYSIOLOGICALLY ACTIVE PROSTAGLAND CONNECTIONS OF THE E AND F SERIES

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6586468B1 (en) 1998-09-14 2003-07-01 Ono Pharmaceutical Co., Ltd. ω-substituted phenyl-prostaglandin E derivatives and drugs containing the same as the active ingredient

Also Published As

Publication number Publication date
NL166015C (en) 1981-06-15
AU8736275A (en) 1977-10-13
ATA941675A (en) 1978-12-15
AT351185B (en) 1979-07-10
NL166015B (en) 1981-01-15
FR2293923B1 (en) 1979-02-23
FI753475A (en) 1976-06-12
IL48617A0 (en) 1976-02-29
DK559975A (en) 1976-06-12
NO754195L (en) 1976-06-14
GB1508169A (en) 1978-04-19
JPS52102258A (en) 1977-08-27
LU73997A1 (en) 1976-11-11
NZ179502A (en) 1979-01-11
IE43815B1 (en) 1981-06-03
CS194746B2 (en) 1979-12-31
IE43815L (en) 1976-06-11
DD129649A5 (en) 1978-02-01
SE7513602L (en) 1976-06-14
CS194733B2 (en) 1979-12-31
FR2293923A1 (en) 1976-07-09
NL7514446A (en) 1976-06-15
GB1508170A (en) 1978-04-19
ZA747723B (en) 1976-11-24
DE2555210A1 (en) 1976-06-16
GR60310B (en) 1978-05-08
JPS52102270A (en) 1977-08-27
BE836564A (en) 1976-06-11
IL56863A0 (en) 1979-05-31
CH610302A5 (en) 1979-04-12
DD129783A5 (en) 1978-02-08
ES443421A1 (en) 1977-04-16
CS194745B2 (en) 1979-12-31
JPS51125257A (en) 1976-11-01
DD125828A5 (en) 1977-05-18

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
48S Specification amended (sect. 8/1949)
SPA Amended specification published
PCNP Patent ceased through non-payment of renewal fee