GB1447031A - Tricyclic sulphones and pharmaceutical compositions containing them - Google Patents
Tricyclic sulphones and pharmaceutical compositions containing themInfo
- 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
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.
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)
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)
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)
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 |
-
1973
- 1973-05-04 GB GB2117473*[A patent/GB1447031A/en not_active Expired
- 1973-05-18 LU LU67622A patent/LU67622A1/xx unknown
- 1973-05-18 DD DD170909A patent/DD108539A5/xx unknown
- 1973-05-18 AR AR248104A patent/AR210237A1/en active
- 1973-05-18 IL IL7350000A patent/IL50000A/en unknown
- 1973-05-18 IL IL7342311A patent/IL42311A/en unknown
- 1973-05-18 IE IE2480/76A patent/IE37646B1/en unknown
- 1973-05-18 CA CA171,774A patent/CA1024987A/en not_active Expired
- 1973-05-18 ES ES414888A patent/ES414888A1/en not_active Expired
- 1973-05-18 AT AT435573A patent/AT336011B/en not_active IP Right Cessation
- 1973-05-18 JP JP48055454A patent/JPS4948657A/ja active Pending
- 1973-05-18 CH CH713973A patent/CH616423A5/de not_active IP Right Cessation
- 1973-05-18 NL NL7306958A patent/NL7306958A/xx not_active Application Discontinuation
- 1973-05-18 IE IE795/73A patent/IE37645B1/en unknown
- 1973-05-18 DE DE2325300A patent/DE2325300A1/en active Pending
- 1973-05-18 US US361523A patent/US3905989A/en not_active Expired - Lifetime
- 1973-05-21 FR FR7318299A patent/FR2185407B1/fr not_active Expired
-
1974
- 1974-08-10 AR AR255012A patent/AR210245A1/en active
-
1975
- 1975-07-16 AR AR259624A patent/AR209311A1/en active
-
1976
- 1976-02-17 FR FR7604263A patent/FR2300088A1/en active Granted
- 1976-02-17 FR FR7604262A patent/FR2293198A1/en active Granted
- 1976-04-15 SE SE7604471A patent/SE7604471L/en unknown
- 1976-07-08 IL IL7650000A patent/IL50000A0/en unknown
- 1976-08-06 AR AR259185D patent/AR206633A1/en active
Cited By (1)
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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