GB1447031A - Tricyclic sulphones and pharmaceutical compositions containing them - Google Patents

Tricyclic sulphones and pharmaceutical compositions containing them

Info

Publication number
GB1447031A
GB1447031A GB2117473*[A GB2117473A GB1447031A GB 1447031 A GB1447031 A GB 1447031A GB 2117473 A GB2117473 A GB 2117473A GB 1447031 A GB1447031 A GB 1447031A
Authority
GB
United Kingdom
Prior art keywords
acid
tetrazolyl
formula
compound
amide
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
GB2117473*[A
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.)
Wellcome Foundation Ltd
Original Assignee
Wellcome Foundation Ltd
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
Priority to GB1955276A priority Critical patent/GB1447032A/en
Application filed by Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd
Priority to GB2117473*[A priority patent/GB1447031A/en
Priority to DD170909A priority patent/DD108539A5/xx
Priority to ES414888A priority patent/ES414888A1/en
Priority to IL7350000A priority patent/IL50000A/en
Priority to CA171,774A priority patent/CA1024987A/en
Priority to JP48055454A priority patent/JPS4948657A/ja
Priority to US361523A priority patent/US3905989A/en
Priority to DE2325300A priority patent/DE2325300A1/en
Priority to IL7342311A priority patent/IL42311A/en
Priority to AT435573A priority patent/AT336011B/en
Priority to CH713973A priority patent/CH616423A5/de
Priority to IE795/73A priority patent/IE37645B1/en
Priority to IE2480/76A priority patent/IE37646B1/en
Priority to NL7306958A priority patent/NL7306958A/xx
Priority to AR248104A priority patent/AR210237A1/en
Priority to LU67622A priority patent/LU67622A1/xx
Priority to FR7318299A priority patent/FR2185407B1/fr
Priority to AU55959/73A priority patent/AU486798B2/en
Priority to US05/394,424 priority patent/US4025635A/en
Priority to AR25501374A priority patent/AR209422A1/en
Priority to AR255012A priority patent/AR210245A1/en
Priority to US05/586,426 priority patent/US4012499A/en
Priority to AR259624A priority patent/AR209311A1/en
Priority to FR7604262A priority patent/FR2293198A1/en
Priority to FR7604263A priority patent/FR2300088A1/en
Priority to SE7604471A priority patent/SE7604471L/en
Priority to IL7650000A priority patent/IL50000A0/en
Priority to AR259185D priority patent/AR206633A1/en
Publication of GB1447031A publication Critical patent/GB1447031A/en
Priority to US05/770,841 priority patent/US4145350A/en
Priority to CA272,677A priority patent/CA1024893A/en
Priority to US05/776,936 priority patent/US4177257A/en
Priority to AU28433/77A priority patent/AU2843377A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/12—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/06—Six-membered rings
    • C07D327/08—[b,e]-condensed with two six-membered carbocyclic rings
    • 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
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/08—Six-membered rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1447031 Tricyclic sulphones WELLCOME FOUNDATION Ltd 17 Aug 1973 [19 May 1972 6 Sept 1972 4 May 1973] 23805/72 and 414291/72 Heading C2C The invention comprises compounds of the formula wherein Z<SP>1</SP> is 5-tetrazolyl or 5-(1- or 2-C 1 -C 6 alkyl)-tetrazolyl where the alkyl groups may be substituted by OH, NH 2 optionally substituted by one or two CH 3 groups or COOH, Z<SP>2</SP> is H, a group such as Z<SP>1</SP>, COOH, (C 1 -C 6 )-alkylsulphonyl, alkylsulphinyl, alkylthio, alkyl or alkoxy, (C 2 -C 7 )-alkanoyl or alkanoylamino, amino, NO 2 , CN or halogen, Z<SP>3</SP> is a bond, -CO-, -O-, -S-, -SO-, or -CH 2 -; or a salt thereof, or when Z<SP>2</SP> is COOH, an ester or amide thereof. They may be obtained by (a) when one or both of Z<SP>1</SP> and Z<SP>2</SP> are tetrazolyl or (l-alkyl)-tetrazolyl, reacting hydrazoic acid or a salt thereof, or nitrous acid with a compound of formula wherein at least one of Y<SP>8</SP> and Y<SP>7</SP> is a tetrazolyl group precursor and the other is a group as defined for Z<SP>1</SP> or Z<SP>2</SP>; (b) when Z<SP>2</SP> is COOH, hydrolysing a compound of the formula wherein Y<SP>1</SP> is the same as Z<SP>1</SP> and Y<SP>2</SP> is carbonyl group precursor, with a base or with a dilute aqueous mineral acid optionally in the presence of an organic acid; (c) oxidizing a compound of the formula wherein Y<SP>5</SP> and Y<SP>3</SP> are the same as Z<SP>1</SP> and Z<SP>3</SP> respectively, Y<SP>4</SP> is -S-, -SO- or -SO 2 - and Y<SP>6</SP> is alkyl, alkanoyl or is the same as Z<SP>2</SP>, provided that when Y<SP>6</SP> is the same as Z<SP>2</SP> then at least Y<SP>4</SP> is -S-or -SO- or Y<SP>3</SP> is -CH 2 - or -S-, with an appropriate oxidizing agent; (d) when Z<SP>3</SP> is -O- or -S-, cyclizing a compound of the formula wherein one of R<SP>2</SP> and R<SP>3</SP> is SH, OH or an ester thereof and the other is a leaving group, with a base; (e) cyclizing a compound of the formula using a Lewis acid; (f) cyclizing a compound of the formula with ClSO 3 H; (g) when Z<SP>3</SP> is -S- or -CH 2 -, reducing the corresponding compound of Formula I wherein Z<SP>3</SP> is -SO- or -CO-, with an appropriate reducing agent; (h) when Z<SP>3</SP> is -S-, reacting a compound of the formula wherein R<SP>5</SP> and R<SP>6</SP> are each leaving groups, with sodium sulphide; or (i) when Z<SP>3</SP> is -CO-, cyclizing a compound of the formula wherein R<SP>1</SP> is -COOH or a derivative thereof or is -CHO, in the presence of a Lewis or protonic acid; and when a salt, an amide or an ester, or an alkyl tetrazolyl compound is required converting the products obtained above by appropriate reactions. Pharmaceutical compositions comprise the compounds of Formula I in association with an acceptable carrier. They are useful as inhibitors of allergic reactions associated with asthma, hay fever, conjunctivitis, urticaria and eczema and may be applied orally, rectally, ophthalmically, pulmonarily, nasally, dermally, topically or parenterally. The preparation of the following intermediates is described: Prep. (1) 3-carboxythioxanthone - 10,10 - dioxide from nitroterephthalonitrile via phenylthioterephthalonitrile, phenylthioterephthalic acid and thioxanthone-3- carboxylic acid; Example (1) 3-cyanothioxanthone-10,10-dioxide from the corresponding carboxylic acid via its carbamoyl derivative; Example (2) 7 - ethyl - 3 - (5 - tetrazolyl) - thioxanthone from 7 - ethylthioxanthone - 3 - carboxylic via 3-cyano-7-ethylthioxanthone; Example (3) 7 - t - butyl - 3 - (5 - tetrazolyl)thioxanthone from 7 - t - butylthioxanthone - 3 - carboxylic acid via its amide and nitrile; Prep. (4) 4- carboxythioxanthone-10,10-dioxide from o-chlorobenzoic acid via its cupric salt, a cupric complex of thiosalicylic acid, diphenyl sulphide - 2,21- dicarboxylic acid and thioxanthone-4-carboxylic acid; Example (4) 4-cyanothioxanthone-10,10- dioxide from the corresponding carboxylic acid via its amide; Prep. (5) 3-carboxythianthrene-5,5- dioxide from 3 - amino - 4 - chlorobenzoic acid via 4 - chloro - 3 - mercaptobenzoic acid, 4- chloro - 3 - (o - nitrophenylthio) benzoic acid and 3 - (o - nitro - and - aminophenylsulphonyl) - 4- chlorobenzoic acids; Example (9) 3-cyanothianthene-5,5-dioxide from the corresponding carboxylic acid via its acid chloride and amide Example (10) 2-cyano-8-methylphenoxathin-10, 10-dioxide from the corresponding carboxylic acid via its acid chloride and amide; Example (12) 7 - chloro - 3 - (5 - tetrazolyl) thioxanthone from p - chlorophenylthioterephthalonitrile via 2 - (p - chlorophenylthio) - 4 - (5 - tetrazolyl) benzonitrile, the corresponding free carboxylic acid and 7 - chloro - 3 - (5 - tetrazolyl) thioxanthone; Example (13) 3-cyanothioxanthone-10,10-dioxide from the corresponding carboxylic acid via its acid chloride and amide; Example (16) 3-(5- tetrazolyl) thioxanthone from the corresponding carboxylic acid via its acid chloride, amide and nitrile; Example (17) 3-cyano-7-methylthioxanthone-10,10-dioxide from the corresponding 3- carbamoyl derivative; Example (18) 2-(5- tetrazolyl) phenoxathiin from phenoxathiin via phenoxathiin-2-aldehyde and 2-cyanophenoxathiin; Example (19) 2-phenylsulphonyl-4-(5- tetrazolyl) benzoic acid from phenylthioterephthalonitrile via 2-phenylthio-4- (5-tetrazolyl)- benzonitrile, the corresponding free carboxylic acid and 2 - phenylsulphonyl - 4 - (5 - tetrazolyl)- benzoic acid; and Example (20) 7-methoxy-3-(5- tetrazolyl) thioxanthone from 7-methoxythioxanthone-3-carboxylic via its acid chloride, amide and nitrile. Other intermediates are described in Specification 1,447,032.
GB2117473*[A 1972-05-19 1973-05-04 Tricyclic sulphones and pharmaceutical compositions containing them Expired GB1447031A (en)

Priority Applications (33)

Application Number Priority Date Filing Date Title
GB1955276A GB1447032A (en) 1972-05-19 1972-05-19 Tricyclic sulphones and pharmaceutical compositions containing them
GB2117473*[A GB1447031A (en) 1972-05-19 1973-05-04 Tricyclic sulphones and pharmaceutical compositions containing them
US361523A US3905989A (en) 1972-05-19 1973-05-18 (Tetrazolyl)thioxanthone-10,10-dioxides
IL7342311A IL42311A (en) 1972-05-19 1973-05-18 Tetrazolyl substituted tricyclic sulphur compounds their preparation and pharmaceutical compositions containing the
IL7350000A IL50000A (en) 1972-05-19 1973-05-18 Pharmaceutical compositions containing carboxythioxanthene (-thioxanthone-phenoxathiine,-thianthrene or -dibenzothiophene) dioxides,certain such novel compounds and their preparation
CA171,774A CA1024987A (en) 1972-05-19 1973-05-18 Cyclic sulphur compounds
JP48055454A JPS4948657A (en) 1972-05-19 1973-05-18
DD170909A DD108539A5 (en) 1972-05-19 1973-05-18
DE2325300A DE2325300A1 (en) 1972-05-19 1973-05-18 CYCLIC SULFUR COMPOUNDS
ES414888A ES414888A1 (en) 1972-05-19 1973-05-18 (Tetrazolyl)thioxanthone-10,10-dioxides
AT435573A AT336011B (en) 1972-05-19 1973-05-18 PROCESS FOR PRODUCING NEW TRICYCLIC COMPOUNDS
CH713973A CH616423A5 (en) 1972-05-19 1973-05-18
IE795/73A IE37645B1 (en) 1972-05-19 1973-05-18 Tricyclic sulphones and pharmaceutical compositions containing them
IE2480/76A IE37646B1 (en) 1972-05-19 1973-05-18 Tricyclic sulphones and pharmaceutical compositions containing them
NL7306958A NL7306958A (en) 1972-05-19 1973-05-18
AR248104A AR210237A1 (en) 1972-05-19 1973-05-18 A METHOD FOR PREPARING COMPOUNDS OF 10,10-THIOXANTONE BIOXIDE
LU67622A LU67622A1 (en) 1972-05-19 1973-05-18
FR7318299A FR2185407B1 (en) 1972-05-19 1973-05-21
AU55959/73A AU486798B2 (en) 1972-05-19 1973-05-21 Cyclic sulphur compounds
US05/394,424 US4025635A (en) 1972-09-06 1973-09-05 Cyclic sulphur compounds
AR25501374A AR209422A1 (en) 1972-05-19 1974-08-01 METHOD FOR PREPARING DERIVATIVES OF 10,10-THIOXANTONE BIOXIDE
AR255012A AR210245A1 (en) 1972-05-19 1974-08-10 METHOD FOR PREPARING DERIVATIVES OF 10,10-THIOXANTHENE BIOXIDE
US05/586,426 US4012499A (en) 1972-05-19 1975-06-12 Cyclic sulphur compounds
AR259624A AR209311A1 (en) 1972-05-19 1975-07-16 METHOD FOR PREPARING DERIVATIVES OF 10,10-PHENOXATIINE BIOXIDE
FR7604262A FR2293198A1 (en) 1972-05-19 1976-02-17 MEDICINAL PRODUCT CONTAINING THIOXANTHONE S-DIOXIDE DERIVATIVE
FR7604263A FR2300088A1 (en) 1972-05-19 1976-02-17 TRICYCLIC COMPOUNDS FOR USE IN THE PREPARATION OF MEDICINAL PRODUCTS
SE7604471A SE7604471L (en) 1972-05-19 1976-04-15 PROCEDURE FOR PREPARING A TRICYCLIC ASSOCIATION
IL7650000A IL50000A0 (en) 1972-05-19 1976-07-08 Tricyclic sulphur compounds,their preparation and pharmaceutical compositions containing them
AR259185D AR206633A1 (en) 1972-05-19 1976-08-06 METHOD FOR PREPARING DERIVATIVES OF 10,10-PHENOXATIINE BIOXIDE
US05/770,841 US4145350A (en) 1972-09-06 1977-02-22 Cyclic sulphur compounds triazolyl substituted phenoxathin 10, 10 dioxides
CA272,677A CA1024893A (en) 1972-05-19 1977-02-25 Pharmaceutical composition containing 3-carboxythioxanthone-10,10-dioxide or salt thereof
US05/776,936 US4177257A (en) 1972-09-06 1977-03-11 Cyclic sulphur compounds
AU28433/77A AU2843377A (en) 1972-05-19 1977-08-31 Phenoxathiin dioxides

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB2380572 1972-05-19
GB4142972 1972-09-06
GB2117473*[A GB1447031A (en) 1972-05-19 1973-05-04 Tricyclic sulphones and pharmaceutical compositions containing them

Publications (1)

Publication Number Publication Date
GB1447031A true GB1447031A (en) 1976-08-25

Family

ID=27257983

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2117473*[A Expired GB1447031A (en) 1972-05-19 1973-05-04 Tricyclic sulphones and pharmaceutical compositions containing them

Country Status (16)

Country Link
US (1) US3905989A (en)
JP (1) JPS4948657A (en)
AR (4) AR210237A1 (en)
AT (1) AT336011B (en)
CA (1) CA1024987A (en)
CH (1) CH616423A5 (en)
DD (1) DD108539A5 (en)
DE (1) DE2325300A1 (en)
ES (1) ES414888A1 (en)
FR (3) FR2185407B1 (en)
GB (1) GB1447031A (en)
IE (2) IE37646B1 (en)
IL (3) IL50000A (en)
LU (1) LU67622A1 (en)
NL (1) NL7306958A (en)
SE (1) SE7604471L (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0004257A1 (en) * 1978-03-09 1979-09-19 Sanofi S.A. Benzonitrile derivative, process for its preparation and its application

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4012517A (en) * 1975-01-24 1977-03-15 Burroughs Wellcome Co. Compositions and treatment
BE837876A (en) * 1975-01-24 1976-07-23 ANTIALLERGIC PHARMACEUTICAL COMPOSITIONS
CH628343A5 (en) * 1977-03-24 1982-02-26 Sandoz Ag Process for preparing thioxanthones
US4536507A (en) * 1977-07-26 1985-08-20 Merck & Co., Inc. Prostaglandin antagonists
US4221800A (en) * 1977-12-23 1980-09-09 Miles Laboratories, Inc. Cycloalkenochromone
US4394515A (en) * 1978-06-23 1983-07-19 Merck & Co., Inc. 10,11-Dihydro-11-oxodibenzo[b,f]thiepin compounds
CH640849A5 (en) * 1979-05-18 1984-01-31 Ciba Geigy Ag THIOXANTHONICARBONIC ACID ESTERS, THIOESTERS AND AMIDES.
US4432986A (en) * 1979-06-18 1984-02-21 Riker Laboratories, Inc. Tetrazoles bonded to certain polycyclic aromatic systems and anti-allergic use thereof
NL8005946A (en) * 1979-11-02 1981-06-01 Hoffmann La Roche AGENTS AGAINST FATIGUE AND INCREASED FAT MIRROR.
US4237160A (en) * 1979-11-27 1980-12-02 Merck Sharp & Dohme (I.A.) Corp. 3-Hydroxymethyldibenzo[b,f]thiepins as prostaglandin antagonists
US4731363A (en) * 1979-12-26 1988-03-15 Hoffmann-La Roche Inc. Thromboxane synthase inhibitors as insulin lowering agents and antiobesity agents
US4500540A (en) * 1979-12-26 1985-02-19 Hoffmann-La Roche Inc. Thromboxane synthase inhibitors as insulin lowering agents and antionbesity agents
JPS5716821A (en) * 1980-07-04 1982-01-28 Yoshitomi Pharmaceut Ind Ltd Remedy for disease due to immunological dysfunction
US4377579A (en) * 1981-12-03 1983-03-22 Minnesota Mining And Manufacturing Company N-(Tetrazol-5-yl)phenazine-1-carboxamides
US4535171A (en) * 1982-11-18 1985-08-13 Merck Frosst Canada, Inc. Dibenzo[b,f]thiepin-3-carboxaldehydes as prostaglandin antagonists
EP0150891A1 (en) * 1984-01-05 1985-08-07 The Wellcome Foundation Limited Tricyclic compounds, processes for their preparation, compositions containing such compounds and their use in medicine
GB8400202D0 (en) * 1984-01-05 1984-02-08 Wellcome Found Tricyclic compounds

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3096343A (en) * 1960-07-20 1963-07-02 Du Pont Method for isolating aromatic carboxylic acids
US3555043A (en) * 1969-02-17 1971-01-12 Sterling Drug Inc Tertiary-amino-lower-alkoxy-9-benzylxanthenes and thioxanthenes
US3642997A (en) * 1969-06-25 1972-02-15 Merck & Co Inc Tricyclic carboxylic acids in the treatment of inflammation
BE759292A (en) * 1969-11-27 1971-05-24 Allen & Hanburys Ltd XANTHONE DERIVATIVES, THEIR PREPARATION AND THEIR USE

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0004257A1 (en) * 1978-03-09 1979-09-19 Sanofi S.A. Benzonitrile derivative, process for its preparation and its application

Also Published As

Publication number Publication date
FR2185407B1 (en) 1977-08-19
AR209311A1 (en) 1977-04-15
JPS4948657A (en) 1974-05-11
DE2325300A1 (en) 1973-12-20
IL50000A (en) 1978-03-10
IL42311A0 (en) 1973-07-30
CA1024987A (en) 1978-01-24
ES414888A1 (en) 1976-06-01
LU67622A1 (en) 1973-11-23
CH616423A5 (en) 1980-03-31
IE37645L (en) 1973-11-19
ATA435573A (en) 1976-08-15
FR2185407A1 (en) 1974-01-04
US3905989A (en) 1975-09-16
IE37646B1 (en) 1977-09-14
IE37645B1 (en) 1977-09-14
AT336011B (en) 1977-04-12
AU5595973A (en) 1974-11-21
SE7604471L (en) 1976-04-15
AR210245A1 (en) 1977-07-15
AR206633A1 (en) 1976-08-06
IL42311A (en) 1978-03-10
DD108539A5 (en) 1974-09-20
FR2300088A1 (en) 1976-09-03
FR2293198B1 (en) 1979-06-29
FR2293198A1 (en) 1976-07-02
AR210237A1 (en) 1977-07-15
IL50000A0 (en) 1976-09-30
FR2300088B1 (en) 1980-04-25
NL7306958A (en) 1973-11-21

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee