IE41777L - Heterocyclic carboxamides. - Google Patents
Heterocyclic carboxamides.Info
- Publication number
- IE41777L IE41777L IE750709A IE70975A IE41777L IE 41777 L IE41777 L IE 41777L IE 750709 A IE750709 A IE 750709A IE 70975 A IE70975 A IE 70975A IE 41777 L IE41777 L IE 41777L
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- acid
- prepared
- compound
- reacting
- Prior art date
Links
- -1 Heterocyclic carboxamides Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 8
- 239000002253 acid Substances 0.000 abstract 6
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 abstract 4
- FHMPFSKGDPKPDJ-UHFFFAOYSA-N 2,3,6-trimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1C FHMPFSKGDPKPDJ-UHFFFAOYSA-N 0.000 abstract 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 2
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 abstract 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 150000004702 methyl esters Chemical class 0.000 abstract 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000001640 fractional crystallisation Methods 0.000 abstract 1
- 230000000855 fungicidal effect Effects 0.000 abstract 1
- 150000002240 furans Chemical class 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/30—Halogen atoms or nitro radicals
-
- 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
- C07D307/04—Heterocyclic compounds containing five-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
- C07D307/18—Heterocyclic compounds containing five-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
- C07D307/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- C07D307/56—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 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
-
- 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
-
- 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
- C07D333/26—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 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
1448810 Furan derivatives CIBA-GEIGY AG 1 April 1975 [2 April 1974 10 Feb 1975] 13332/75 Heading C2C The invention comprises compounds of the Formula (I) in which R is H or methyl. They may be prepared by (a) acylating a compound of Formula (II) with furan (2)-carboxylic acid or an acid halide, anhydride or ester thereof, or (b) reacting a compound of Formula (III) with either an α-halopropionic acid methyl ester in the presence of an alkali metal carbonate, or with butyl lithium or sodium hydride to give the corresponding alkali metal salt, followed by reaction with an α-halopropionic acid methyl ester. The enantiomeric D-form of the compound of Formula (I) may be prepared by reacting the racemic compound of Formula (IV) in known manner with a nitrogen-containing optically active base to give the corresponding salt followed by fractional crystallization and liberation of the acid of Formula IV which is enriched with the optical D-antipode. The D- form of the ester of Formula (II) may then be prepared in conventional manner from the D form of the acid of Formula (IV), followed by acylation as in step (a) above, to give the D- form of the compound of Formula (I). The D- form of the acid of Formula (IV) may also be prepared by replacing the hydroxy group in L(+) lactic acid by halogen and reacting this product with 2,6-dimethylaniline or 2,3,6-trimethylaniline with reversal of the configuration. The compounds of Formula (II) may be prepared by reacting 2,6-dimethylaniline or 2,3,6- trimethylaniline with 2-bromopropionic acid methyl ester. The compounds of Formula (I) are used in fungicidal compositions.
[GB1448810A]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH457274A CH590608A5 (en) | 1974-04-02 | 1974-04-02 | N-Furoyl-N-aryl-alanine esters - prepd. e.g. by reacting N-aryl-alanine esters with 2-furoic acid or its derivs. |
| CH159175A CH603041A5 (en) | 1974-04-02 | 1975-02-10 | N-Furoyl-N-aryl-alanine esters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE41777L true IE41777L (en) | 1975-10-02 |
| IE41777B1 IE41777B1 (en) | 1980-03-26 |
Family
ID=25688094
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE708/75A IE41140B1 (en) | 1974-04-02 | 1975-04-02 | Fungicidal n-substituted furoic amide derivatives |
| IE709/75A IE41777B1 (en) | 1974-04-02 | 1975-04-02 | Fungicidal agents |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE708/75A IE41140B1 (en) | 1974-04-02 | 1975-04-02 | Fungicidal n-substituted furoic amide derivatives |
Country Status (31)
| Country | Link |
|---|---|
| JP (3) | JPS6042202B2 (en) |
| AR (2) | AR205189A1 (en) |
| AT (2) | AT345614B (en) |
| AU (1) | AU465906B2 (en) |
| BG (2) | BG24651A3 (en) |
| CA (2) | CA1050546A (en) |
| CH (1) | CH603041A5 (en) |
| CS (2) | CS183788B2 (en) |
| DD (3) | DD118510A5 (en) |
| DE (2) | DE2560591C2 (en) |
| DK (2) | DK141995B (en) |
| EG (2) | EG11640A (en) |
| ES (2) | ES436175A1 (en) |
| FI (2) | FI63567C (en) |
| FR (2) | FR2265748B1 (en) |
| GB (2) | GB1498199A (en) |
| HU (2) | HU172935B (en) |
| IE (2) | IE41140B1 (en) |
| IL (2) | IL46988A (en) |
| IT (2) | IT1049394B (en) |
| LU (2) | LU72174A1 (en) |
| NL (2) | NL160821C (en) |
| NO (2) | NO142714C (en) |
| OA (2) | OA04916A (en) |
| PH (2) | PH11792A (en) |
| PL (2) | PL97786B1 (en) |
| RO (3) | RO73181A (en) |
| SE (2) | SE418086B (en) |
| SU (4) | SU682096A3 (en) |
| TR (2) | TR18508A (en) |
| YU (2) | YU39026B (en) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5845433B2 (en) * | 1975-02-10 | 1983-10-08 | チバ・ガイギ− アクチエンゲゼルシヤフト | 2↓-Production method of furancarboxylic acid anilides |
| US4147792A (en) * | 1977-02-04 | 1979-04-03 | Ciba-Geigy Corporation | Fungicidal compositions |
| CH629939A5 (en) * | 1977-03-29 | 1982-05-28 | Ciba Geigy Ag | MICROBICIDAL AGENT. |
| DE2724785A1 (en) * | 1977-05-27 | 1978-12-14 | Schering Ag | FURANCARBONIC ANILIDES, FUNGICIDALS CONTAINING THESE COMPOUNDS AND THE PROCESS FOR THEIR PREPARATION |
| BG28977A3 (en) | 1978-02-02 | 1980-08-15 | Montedison Spa | Fungicide means and method for fungus fighting |
| CH637368A5 (en) * | 1978-10-27 | 1983-07-29 | Ciba Geigy Ag | ANILINE DERIVATIVES AND Pesticides Manufactured From Them. |
| EP0010673B1 (en) * | 1978-10-31 | 1982-01-27 | Bayer Ag | Substituted n-propargyl anilines, process for their preparation and their use as fungicides |
| CH641760A5 (en) * | 1978-11-27 | 1984-03-15 | Ciba Geigy Ag | PEST CONTROL. |
| CH639940A5 (en) * | 1978-12-05 | 1983-12-15 | Ciba Geigy Ag | Substituted N-alkoxycarbonylethyl-N-acylanilines, microbicides containing them, and process for the preparation of the compounds |
| DE2948734A1 (en) * | 1978-12-07 | 1980-06-19 | Ciba Geigy Ag | PEST CONTROL |
| DE2940189A1 (en) | 1979-10-04 | 1981-04-16 | Basf Ag, 6700 Ludwigshafen | ISOXAZOLYLCARBONIC ACID ANILIDE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES |
| MA19111A1 (en) * | 1979-10-26 | 1981-12-31 | Ciba Geigy Ag | HOMOSERIN DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR USE AS MICROBICIDES |
| DE3013908A1 (en) * | 1980-04-11 | 1981-10-22 | Basf Ag, 6700 Ludwigshafen | 2- (N-ARYL-, N-ISOXAZOLYLCARBONYL) -AMINOBUTYROLACTONE, METHOD FOR THE PRODUCTION THEREOF AND FUNGICIDES CONTAINING THEM |
| MA19215A1 (en) * | 1980-07-25 | 1982-04-01 | Ciba Geigy Ag | NOVEL ARYLAMINE DERIVATIVES, PROCESS FOR THEIR MANUFACTURE AND USE AS MICROBICIDES. |
| DE3030736A1 (en) | 1980-08-14 | 1982-03-25 | Basf Ag, 6700 Ludwigshafen | N-DISUBSTITUTED ANILINE DERIVATIVES, THEIR PRODUCTION, THEIR USE AS MICROBICIDES AND AGENTS THEREFOR |
| EP0061836B1 (en) * | 1981-03-19 | 1986-12-30 | Imperial Chemical Industries Plc | Amide derivatives, processes for preparing them, their use as fungicides and pesticidal compositions containing them |
| DE3133418A1 (en) * | 1981-08-24 | 1983-03-10 | Basf Ag, 6700 Ludwigshafen | THIAZOLYL AND ISOTHIAZOLYLCARBONIC ACID ANILIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES |
| JPH0326906U (en) * | 1989-07-26 | 1991-03-19 | ||
| DE4011172A1 (en) * | 1990-04-06 | 1991-10-10 | Degussa | COMPOUNDS FOR CONTROLLING PLANT DISEASES |
| DE4304172A1 (en) | 1993-02-12 | 1994-08-25 | Bayer Ag | Fungicidal active ingredient combinations |
| US5723491A (en) | 1994-07-11 | 1998-03-03 | Novartis Corporation | Fungicidal composition and method of controlling fungus infestation |
| DE4429014A1 (en) | 1994-08-16 | 1996-02-22 | Basf Ag | Process for the preparation of cyclic amines |
| PE32799A1 (en) * | 1996-12-25 | 1999-04-09 | Agrogene Ltd | NEW DERIVATIVE OF AMINOBUTIRIC ACID FOR THE PROTECTION OF FUNGAL DISEASES |
| DE10347090A1 (en) | 2003-10-10 | 2005-05-04 | Bayer Cropscience Ag | Synergistic fungicidal drug combinations |
| DE10349501A1 (en) | 2003-10-23 | 2005-05-25 | Bayer Cropscience Ag | Synergistic fungicidal drug combinations |
| DE102004049761A1 (en) | 2004-10-12 | 2006-04-13 | Bayer Cropscience Ag | Fungicidal drug combinations |
| DE102005026482A1 (en) | 2005-06-09 | 2006-12-14 | Bayer Cropscience Ag | Active substance combination, useful e.g. for combating unwanted phytopathogenic fungus, comprises herbicides e.g. glyphosate and active substances e.g. strobilurin, triazoles, valinamide and carboxamide |
| EP2255648A3 (en) | 2005-06-09 | 2011-03-02 | Bayer CropScience AG | Agent combinations |
| DE102006023263A1 (en) | 2006-05-18 | 2007-11-22 | Bayer Cropscience Ag | Synergistic drug combinations |
| CA2661170A1 (en) | 2006-09-18 | 2008-03-27 | Basf Se | Pesticidal mixtures |
| BR122019020360B1 (en) | 2007-02-06 | 2020-08-18 | Basf Se | mixtures, pesticide composition, method to control harmful phytopathogenic fungi, method to protect plants from attack or infestation by insects, mites or nematodes and method to protect seed |
| EP2000028A1 (en) | 2007-06-06 | 2008-12-10 | Bayer CropScience Aktiengesellschaft | Fungicidal active agent compounds |
| EP2000030A1 (en) | 2007-06-06 | 2008-12-10 | Bayer CropScience AG | Fungicidal active agent compounds |
| RU2339635C1 (en) * | 2007-06-26 | 2008-11-27 | Государственное образовательное учреждение высшего профессионального образования "Российский химико-технологический университет им. Д.И. Менделеева "(РХТУ им. Д.И. Менделеева) | Pyridylmethylanilides of heterocyclic acids, possessing fungicidal activity |
| DE102007045920B4 (en) | 2007-09-26 | 2018-07-05 | Bayer Intellectual Property Gmbh | Synergistic drug combinations |
| AU2010272872B2 (en) | 2009-07-16 | 2014-08-28 | Bayer Intellectual Property Gmbh | Synergistic active substance combinations containing phenyl triazoles |
| EP2910126A1 (en) | 2015-05-05 | 2015-08-26 | Bayer CropScience AG | Active compound combinations having insecticidal properties |
| CN115557887B (en) * | 2022-11-10 | 2024-11-01 | 南京林业大学 | Ugi reaction-based synthesis of trifluoromethyl pyridine derivative and biological activity research thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3959481A (en) * | 1969-02-13 | 1976-05-25 | Uniroyal | Method of protecting plants from fungal diseases using furan-3-carboxamide derivatives |
| JPS5345364A (en) * | 1976-10-06 | 1978-04-24 | Daiahoiru Kk | Device for controlling extrusion molding die bolt |
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1975
- 1975-01-01 AR AR258203A patent/AR205189A1/en active
- 1975-02-10 CH CH159175A patent/CH603041A5/en not_active IP Right Cessation
- 1975-03-26 DK DK135975AA patent/DK141995B/en not_active IP Right Cessation
- 1975-03-26 NO NO751086A patent/NO142714C/en unknown
- 1975-03-26 SE SE7503518A patent/SE418086B/en not_active IP Right Cessation
- 1975-03-26 DK DK135875AA patent/DK141168B/en not_active IP Right Cessation
- 1975-03-26 NO NO751084A patent/NO141340C/en unknown
- 1975-03-26 FI FI750920A patent/FI63567C/en not_active IP Right Cessation
- 1975-03-26 FR FR7509485A patent/FR2265748B1/fr not_active Expired
- 1975-03-26 FI FI750921A patent/FI750921A7/fi not_active Application Discontinuation
- 1975-03-26 FR FR7509484A patent/FR2265747B1/fr not_active Expired
- 1975-03-26 SE SE7503517A patent/SE419218B/en not_active IP Right Cessation
- 1975-03-27 AU AU79640/75A patent/AU465906B2/en not_active Expired
- 1975-03-27 NL NL7503754.A patent/NL160821C/en not_active IP Right Cessation
- 1975-03-27 CA CA223,227A patent/CA1050546A/en not_active Expired
- 1975-03-27 DE DE2560591A patent/DE2560591C2/de not_active Expired
- 1975-03-27 NL NL7503755A patent/NL7503755A/en not_active Application Discontinuation
- 1975-03-27 CA CA223,222A patent/CA1050558A/en not_active Expired
- 1975-03-27 DE DE19752513732 patent/DE2513732A1/en active Granted
- 1975-03-28 IT IT21867/75A patent/IT1049394B/en active
- 1975-03-28 IT IT21855/75A patent/IT1048806B/en active
- 1975-03-31 OA OA55458A patent/OA04916A/en unknown
- 1975-03-31 OA OA55460A patent/OA04918A/en unknown
- 1975-03-31 PH PH16995A patent/PH11792A/en unknown
- 1975-03-31 PH PH16998A patent/PH13072A/en unknown
- 1975-04-01 HU HU75CI00001563A patent/HU172935B/en not_active IP Right Cessation
- 1975-04-01 GB GB13349/75A patent/GB1498199A/en not_active Expired
- 1975-04-01 DD DD185144A patent/DD118510A5/xx unknown
- 1975-04-01 AR AR258204A patent/AR224602A1/en active
- 1975-04-01 YU YU00828/75A patent/YU39026B/en unknown
- 1975-04-01 DD DD185147A patent/DD118785A5/xx unknown
- 1975-04-01 RO RO7581867A patent/RO73181A/en unknown
- 1975-04-01 AT AT244675A patent/AT345614B/en not_active IP Right Cessation
- 1975-04-01 YU YU827/75A patent/YU40259B/en unknown
- 1975-04-01 BG BG029507A patent/BG24651A3/en unknown
- 1975-04-01 IL IL46988A patent/IL46988A/en unknown
- 1975-04-01 LU LU72174A patent/LU72174A1/xx unknown
- 1975-04-01 ES ES436175A patent/ES436175A1/en not_active Expired
- 1975-04-01 GB GB1333275A patent/GB1448810A/en not_active Expired
- 1975-04-01 BG BG029508A patent/BG26356A3/en unknown
- 1975-04-01 AT AT244875A patent/AT343407B/en not_active IP Right Cessation
- 1975-04-01 LU LU72175A patent/LU72175A1/xx unknown
- 1975-04-01 DD DD192060A patent/DD124733A5/xx unknown
- 1975-04-01 ES ES436174A patent/ES436174A1/en not_active Expired
- 1975-04-01 HU HU75CI1564A patent/HU173317B/en unknown
- 1975-04-01 IL IL46989A patent/IL46989A/en unknown
- 1975-04-02 CS CS7500002239A patent/CS183788B2/en unknown
- 1975-04-02 PL PL1975179266A patent/PL97786B1/en unknown
- 1975-04-02 EG EG194/75A patent/EG11640A/en active
- 1975-04-02 EG EG75195A patent/EG12263A/en active
- 1975-04-02 RO RO106426A patent/RO84021B/en unknown
- 1975-04-02 IE IE708/75A patent/IE41140B1/en unknown
- 1975-04-02 CS CS7500002240A patent/CS183789B2/en unknown
- 1975-04-02 TR TR18508A patent/TR18508A/en unknown
- 1975-04-02 RO RO7581876A patent/RO79677A/en unknown
- 1975-04-02 JP JP50040227A patent/JPS6042202B2/en not_active Expired
- 1975-04-02 PL PL1975179265A patent/PL98627B1/en unknown
- 1975-04-02 JP JP4022675A patent/JPS5345364B2/ja not_active Expired
- 1975-04-02 SU SU752120455A patent/SU682096A3/en active
- 1975-04-02 TR TR18339A patent/TR18339A/en unknown
- 1975-04-02 IE IE709/75A patent/IE41777B1/en unknown
- 1975-04-02 SU SU752121601A patent/SU743561A3/en active
- 1975-11-05 SU SU752186207A patent/SU628812A3/en active
-
1976
- 1976-04-05 SU SU762342705A patent/SU626690A3/en active
-
1978
- 1978-01-12 JP JP232778A patent/JPS53135964A/en active Granted
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