US3212892A - Preventing darkening and formation of precipitates in solutions of photographic developers - Google Patents

Preventing darkening and formation of precipitates in solutions of photographic developers Download PDF

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Publication number
US3212892A
US3212892A US126521A US12652161A US3212892A US 3212892 A US3212892 A US 3212892A US 126521 A US126521 A US 126521A US 12652161 A US12652161 A US 12652161A US 3212892 A US3212892 A US 3212892A
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Prior art keywords
developer
formation
precipitates
solutions
substituted
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US126521A
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English (en)
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Konig Anita Von
Pfeiffenschneider Raymund
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Agfa Gevaert NV
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Agfa AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen atoms
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
    • G03C5/29—Development processes or agents therefor
    • G03C5/305—Additives other than developers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C8/00—Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
    • G03C8/24—Photosensitive materials characterised by the image-receiving section
    • G03C8/243—Toners for the silver image

Definitions

  • This invention relates to compounds being capable of preventing darkening and the formation of precipitates in solutions of photographic developers. It is known that used solutions of developers darken and that in those developers metallic silver precipitates. This is particularly the case in fixing developers and in developers for the silver salt dilfusion process, because in these special processes silver halide is dissolved out from unexposed and undeveloped material to be treated. The silver compounds which are dissolved are generally not stable in the developer solutions and are reduced, forming metallic silver.
  • This precipitation of silver produces stains because the silver gets deposited on the photographic materials.
  • R represents a radical such as alkyl with 3-16 carbon atoms cycloalkyl, aryl or aralkyl which in turn may be "ice
  • R represents a radical such as alkyl with 3-16 carbon atoms cycloalkyl, aryl or aralkyl which in turn may be "ice
  • the following compounds are very useful for the instant purpose:
  • R1 n-octyl 89-91
  • R n-dodecyl 87-88
  • R1 cyelohexylm 184
  • R1 4-methylcyclohexyl 156-158
  • R1 benzy1 139.
  • R 4-diphenylene 283
  • R 4-methylphenylen 218-219
  • R1 4-methoxyphenylene 186-187
  • R 4-cyclohexylphenyleue- 175-177 R; B-phenylethyl 152-153. 5
  • the compound of the general Formula I can be prepared without difliculties according to one of the following methods: e.g. compounds 1-16 by reacting 2,5-dimercaptothiadiazole with halogen-substituted alkanes in the presence of alkali-metal hydroxide.
  • COMPOUND 3 3 g. (0.2 mol) of 2,5-dirnercapto-1,3,4-thiadiazole are dissolved in 240 cm. of 80% aqueous ethanol containing 8 g. (0.2 mol) sodium hydroxide. After adding 33 g. (0.2 mol) of l-bromohexane the reaction mixture is refluxed for 12 hours and thereafter concentrated by evapo- COMPOUND This compound is prepared according to the method described herein for the preparation of compound 3 with the exception that 27.4 g. of 2-chlorobutane are added and the reaction mixture is refluxed for 13 hours.
  • COMPOUND 12 30 g. (0.2 mol) of 2,5-dimercapto-1,3,4-thiadiazole are dissolved in 240 cm. of 80% aqueous ethanol containing 8 g. (0.2 mol) sodium hydroxide. After adding 25.3 g. (0.2 mol) of benzyl chloride the reaction mixture is refluxed for 2 hours. The product which precipitates after cooling is filtered by suction and washed with water until free from halogen. For purification the raw product is dissolved in dilute aqueous potassium hydroxide and reprecipitated with dilute hydrochloric acid.
  • Compounds 17-29 may be produced by reacting substituted thiosemicarbazide with carbondisulphide according to the following method:
  • COMPOUND 21 43.3 g. (0.25 mol) of 4-cyclohexylthiosemicarbazide 35 cm. of carbon disulphide are added dropwise to this solution with stirring at room temperature. The reaction mixture is then heated for 90 minutes to 65 C. and stirred at this temperature until the evolution of hydrogen sulphide is completed. The product is precipitated by stirring into ice-cooled hydrochloric acid. The precipitated product is separated by suction filtration and washed with water until free from halogen. The crude product is purified by reprecipitation.
  • COMPOUND 24 This compound was prepared in accordance with the method described by Martin Freund and Hans Imgart in Berichte der anno chemischen Deutschen, vol. 28, pages 946957 (1895).
  • the compounds of the general Formula II may be prepared according to one of the following methods: e.g. compounds 30-35 by reacting 2,5-dimercapto-1,3,4-thiadiazole with a,w-dihalogen-alkanes in alcoholic solution in the presence of alkali hydroxide; compounds 3641 according to the method described herein for the preparation of compound 21.
  • COMPOUND 31 30 g. (0.2 mol) 2,5-dimercapto-1,3,4-thiadiazole are dissolved in 240 cm. of aqueous ethanol containing 8 g. (0.2 mol) of sodium hydroxide. After adding 24.4 g. (0.1 mol) of 1,6-dibromohexane it is refluxed for one hour. Thereafter it is cooled and the precipitate suction filtered and washed with Water until free from halogen. The raw product is dissolved in dilute potassium hydroxide and reprecipitated by adding dilute hydrochloric acid.
  • COMPOUND 34 30 g. (0.2 mol) 2,5-dimercapto-1,3,4-thiadiazole are dissolved in 240 cm. of 80% aqueous ethanol containing 8 g. (0.2 mol) of sodium hydroxide. After adding 17.5 g. (0.1 mol) of 1,4-bis-chloromethylbenzol the reaction mixture is refluxed for 2 hours and cooled. The precipitate is filtered by suction and washed with water until free from halogen. The raw material is dissolved in dimethylformamide and reprecipitated by adding water.
  • the compounds having the general Formula III may be prepared by the method described by Hiroshi Kato and Masaki Ohta in the Journal of the Chemical Society of Japan, Pure Chemistry Section [Nippon Kagaku Zassi], vol. 78, pages 1588-91 (November 1957), abstracts of which appear in Chemical Abstracts, vol. 54, column 1502b (1960) and in Chemisches Monbla-tt, 1958 volume, page 13,775 according to the following example:
  • the quantity of mercaptothiadiazole which has to be added depends on the composition of the developer and the effect desired, and varies between 10 and 100 mg. per litre ofdeveloper solution.
  • Example 1 A developer containing per litre of water:
  • Example 2 20-40 mg. of substance 10 are added to a developer as in Example 1. After 100 copies have been made, this developer is still pale in colour. No muddy deposits have been observed. i
  • Example 3 If 35 mg. of substance 21 are added to a developer as in Example 1, there is no darkening of colour even after 100 copies have been made.
  • Example 4 80 mg. of substance 32 are added to the same developer as in Example 1. Even after 100 copies had been made, the developer solution remains considerably paler than a developer without the additive which was used accordingly.
  • Example 5 A developer containing per litre of water:
  • a developer of the same constitution but containing 80 mg./l. of substance 31 remains pale yellow in colour after the same number of copies have passed through it. No precipitate has been observed.
  • Example 6 4O mg./1. of substance 34 are added to the developer as in Example 3. The developer is still pale after 100 copies have been made.
  • Example 7 50 mg. of substance 3 are added to the developer as in Example 3. After 75 copies have been made, the developer is still pale yellow in colour and produces no stains on the copies.
  • Example 8 20-30 mg. of substance 12 are added to a developer as in Example 3. After 75-100 copies have been made, no formation of deposit is observed. A developer of the same constitution but Without the additive is after 75 copies have been processed already darkened and contains a muddy precipitate.
  • Example 9 A developer containing per litre of water:
  • the foregoing examples were selected to illustrate the present invention, it being understood that these examples represent preferred embodiments but are not to be considered as limiting the invention thereto.
  • the remainder of the developer composition are not critical and are selected according to the requirements of the particular reproduction process for which the developer composition is to be used.
  • developer compounds may be utilized hydroquinone, p-methylaminophenol, 1-phenyl-3-pyrazolidone, 1-p-aminophenyl-3-amino-pyraz 'olone, phenylendiamine derivatives and the like.
  • the developer may contain antioxidants such as alkali-metal sulphites, bisulphites, metasulfites or metahydrogen sulphites or any conventional stabilizing agent.
  • the developer composition can be alkalized with alkali-metal hydroxides, phosphates, borates, carbonates and the like.
  • the developer com-positions according to the invention may be used for processing of any kind of photographic material.
  • the compounds according to the invention are preferably added to developer compositions that are intended to be used in the silver salt diifusion process said compounds can also be employed in compositions for developing black and white or color photographic materials.
  • R is a radical of the group consisting of alkyl containing from 3 to 16 carbon atoms, cycloalkyl, phenyl, phenylalkyl, and halogen-substituted, alkoxy-substituted, lower-ailkyl-substituted, cycloalkyl-substituted, and phenyl-substituted cycloalkyl, phenyl, phenylalkyl, and alkyl radicals containing from 3 to 16 carbon atoms,
  • R is a radical of the group consisting of alkylene containing from 4 to 10 carbon atoms, cycloalkylene, phenylene, phenylalkylene, and halogen-substituted, alkoxy-substit-uted and lower-alkyl-substituted cycloalkylene, phenylene, phenylalkylene and alkylene radicals containing from 4 to 10 carbon atoms, and
  • n is an integer from 0 to 6.
  • the developer composition contains a silver halide solvent selected from the group consisting of sodium thiosulphate, potassium thiosulphate, calcium thiosulphate and ammonium thiosulphate.
  • R is a radical of the group consisting of alkyl containing from 3 to 16 carbon atoms, cycloalkyl, phenyl, phenylalkyl, and halogen-substituted, aikoxy-su-bstituted, lower-alkyl-substituted, cycloalkyl-substituted, and phenyl-su-bstituted cycloalkyl, phenyl, phenylalkyl, and alkyl radicals containing from 3 to 16 carbon atoms,
  • R is a radical of the group consisting of alkylene containing from 4 to 10 carbon atoms, cycloalkylene, phenylene, phenylalkylene, and halogen-substituted, alkoxy-substituted and lower-alkyl-substituted cycloalkylene, phenylene, phenylalkylene and alkylene radicals containing from 4 to 10 carbon atoms, and
  • n is an integer from to 6, in an amount sufficient to prevent darkening and the formation of precipitates in the composition.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US126521A 1960-07-27 1961-07-25 Preventing darkening and formation of precipitates in solutions of photographic developers Expired - Lifetime US3212892A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEA35212A DE1175077B (de) 1960-07-27 1960-07-27 Verfahren zur Verhinderung der Dunkel-faerbung und Schlammbildung in photo-graphischen Entwicklern

Publications (1)

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US3212892A true US3212892A (en) 1965-10-19

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BE (1) BE606550A (en))
CH (1) CH399903A (en))
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GB (3) GB940169A (en))

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3362826A (en) * 1963-04-27 1968-01-09 Agfa Ag Photographic paper containing yellow fog-preventing agents
US3364028A (en) * 1963-04-27 1968-01-16 Agfa Ag Photographic material containing yellow fog-preventing agents
US3617289A (en) * 1966-12-10 1971-11-02 Fuji Photo Film Co Ltd Stabilization process for thermally developable light-sensitive elements
US3718468A (en) * 1969-04-15 1973-02-27 Agfa Gevaert Ag Stabilising developed photographic images
US4093462A (en) * 1976-11-11 1978-06-06 Eastman Kodak Company 2,5-Bis(secondary amino) oxa- and thiadiazole photographic developing agents
US4371610A (en) * 1980-07-24 1983-02-01 Fuji Photo Film Co., Ltd. Process for development-processing silver halide light-sensitive material
US4675274A (en) * 1984-07-19 1987-06-23 Fuji Photo Film Co., Ltd. Method for developing color reversal photographic materials
US4761482A (en) * 1987-04-23 1988-08-02 R. T. Vanderbilt Company, Inc. Terpene derivatives of 2,5-dimercapto-1,3,4-thiadiazoles and lubricating compositions containing same
US4933265A (en) * 1986-09-01 1990-06-12 Fuji Photo Film Co., Ltd. Process for forming direct positive color image
EP0899611A1 (en) * 1997-08-26 1999-03-03 Eastman Kodak Company Photographic developing composition containing anti-sludging agents and use thereof
US6620771B2 (en) * 1999-10-20 2003-09-16 R. T. Vanderbilt Company, Inc. Thiadiazole dimer additives and lubricating compositions containing the same
WO2008061796A3 (en) * 2006-11-24 2009-07-23 Ac Immune Sa Compounds for the treatment of diseases associated with amyloid or amyloid-like proteins
US20100183513A1 (en) * 2006-11-24 2010-07-22 Wolfgang Froestl N-(methyl) -1h-pyrazol-3-amine, n-(methyl)-pyridin-2-amine and n-(methyl)-thiazol-2-amine derivatives for the treatment of diseases associated with amyloid or amyloid-like proteins, like e.g. alzheimer's
US20110092537A1 (en) * 2009-10-15 2011-04-21 Ac Immune S.A. 2,6-Diaminopyridine Compounds Suitable For Treating Diseases Associated With Amyloid Or Amyloid-Like Proteins Or For Treating Or Preventing Ocular Diseases Or Conditions Associated With A Pathological Abnormality/Change In The Tissue Of The Visual System
WO2021055388A1 (en) 2019-09-17 2021-03-25 The Lubrizol Corporation 2,5-dimercapto-1,3,4-thiadiazole ("dmtd") derivatives
WO2022046718A1 (en) 2020-08-26 2022-03-03 The Lubrizol Corporation 2,5-dimercapto-1,3,4-thiadiazole (dmtd) zinc salt derivatives
WO2022046625A1 (en) 2020-08-26 2022-03-03 The Lubrizol Corporation 2,5-dimercapto-1,3,4-thiadiazole ("dmtd") metal salt derivatives
CN114805244A (zh) * 2022-05-19 2022-07-29 贵州大学 双-(1,3,4-噻二唑)类衍生物及其制备方法和应用

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61282841A (ja) * 1985-06-07 1986-12-13 Fuji Photo Film Co Ltd ハロゲン化銀カラ−感光材料の処理方法
JP2591616B2 (ja) 1986-04-22 1997-03-19 コニカ株式会社 カブリの防止されたハロゲン化銀写真感光材料の処理方法
US5310629A (en) * 1991-06-28 1994-05-10 Eastman Kodak Company Silver recovery element and method
US5210009A (en) * 1991-06-28 1993-05-11 Eastman Kodak Company Silver recovery element and process
US5188662A (en) * 1991-06-28 1993-02-23 Eastman Kodak Company Silver recovery process
JP3240334B2 (ja) * 1992-10-12 2001-12-17 コニカ株式会社 黒白ハロゲン化銀写真感光材料の現像処理方法
US5506092A (en) * 1993-12-06 1996-04-09 Konica Corporation Method of processing black and white silver halide photographic compositions with a developer containing an anti sludgant
US5660972A (en) * 1994-03-16 1997-08-26 Mitsubishi Paper Mills Limited Method for photographic development using a filter to inhibit occurrence of silver sludges
DE4424680A1 (de) 1994-07-13 1996-01-18 Rhein Chemie Rheinau Gmbh Poly[2.5-bis(polysulfano)-1.3.4-thiadiazole]
US5683859A (en) * 1996-05-20 1997-11-04 Eastman Kodak Company Photographic developing composition containing a sludge inhibiting agent and use thereof in the high contrast development of nucleated photographic elements
US5840471A (en) 1996-10-02 1998-11-24 Konica Corporation Method for processing silver halide photographic light-sensitive material

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2514650A (en) * 1946-04-05 1950-07-11 Eastman Kodak Co Photographic developing with addition products to improve image quality
US2592195A (en) * 1939-12-20 1952-04-08 Gevaert Photo Prod Nv Heterocyclic nitrogen compounds
US2719126A (en) * 1952-12-30 1955-09-27 Standard Oil Co Corrosion inhibitors and compositions containing same
US2736729A (en) * 1953-08-20 1956-02-28 Basf Ag Substitution products of 1,3,4-thiadiazole and process
US2743184A (en) * 1954-05-03 1956-04-24 Eastman Kodak Co Photographic antiplumming agents and emulsions containing them
DE950537C (de) * 1954-08-06 1956-10-11 Filmfabrik Agfa Wolfen Veb Verfahren zur Klarhaltung von photographischen Halogensilberemulsionen bei der Entwicklung
US3020155A (en) * 1956-05-23 1962-02-06 Eastman Kodak Co Photographic diffusion transfer process
US3083097A (en) * 1957-04-26 1963-03-26 Agfa Ag Bleaching silver images in the formation of printing plates

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT160168B (de) * 1937-09-15 1941-02-25 Gevaert Photo Prod Nv Entwicklungsverfahren für photographische Halogensilberschichten.

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2592195A (en) * 1939-12-20 1952-04-08 Gevaert Photo Prod Nv Heterocyclic nitrogen compounds
US2514650A (en) * 1946-04-05 1950-07-11 Eastman Kodak Co Photographic developing with addition products to improve image quality
US2719126A (en) * 1952-12-30 1955-09-27 Standard Oil Co Corrosion inhibitors and compositions containing same
US2736729A (en) * 1953-08-20 1956-02-28 Basf Ag Substitution products of 1,3,4-thiadiazole and process
US2743184A (en) * 1954-05-03 1956-04-24 Eastman Kodak Co Photographic antiplumming agents and emulsions containing them
DE950537C (de) * 1954-08-06 1956-10-11 Filmfabrik Agfa Wolfen Veb Verfahren zur Klarhaltung von photographischen Halogensilberemulsionen bei der Entwicklung
US3020155A (en) * 1956-05-23 1962-02-06 Eastman Kodak Co Photographic diffusion transfer process
US3083097A (en) * 1957-04-26 1963-03-26 Agfa Ag Bleaching silver images in the formation of printing plates

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3362826A (en) * 1963-04-27 1968-01-09 Agfa Ag Photographic paper containing yellow fog-preventing agents
US3364028A (en) * 1963-04-27 1968-01-16 Agfa Ag Photographic material containing yellow fog-preventing agents
US3617289A (en) * 1966-12-10 1971-11-02 Fuji Photo Film Co Ltd Stabilization process for thermally developable light-sensitive elements
US3718468A (en) * 1969-04-15 1973-02-27 Agfa Gevaert Ag Stabilising developed photographic images
US4093462A (en) * 1976-11-11 1978-06-06 Eastman Kodak Company 2,5-Bis(secondary amino) oxa- and thiadiazole photographic developing agents
US4371610A (en) * 1980-07-24 1983-02-01 Fuji Photo Film Co., Ltd. Process for development-processing silver halide light-sensitive material
US4675274A (en) * 1984-07-19 1987-06-23 Fuji Photo Film Co., Ltd. Method for developing color reversal photographic materials
US4933265A (en) * 1986-09-01 1990-06-12 Fuji Photo Film Co., Ltd. Process for forming direct positive color image
US4761482A (en) * 1987-04-23 1988-08-02 R. T. Vanderbilt Company, Inc. Terpene derivatives of 2,5-dimercapto-1,3,4-thiadiazoles and lubricating compositions containing same
EP0899611A1 (en) * 1997-08-26 1999-03-03 Eastman Kodak Company Photographic developing composition containing anti-sludging agents and use thereof
US6620771B2 (en) * 1999-10-20 2003-09-16 R. T. Vanderbilt Company, Inc. Thiadiazole dimer additives and lubricating compositions containing the same
WO2008061796A3 (en) * 2006-11-24 2009-07-23 Ac Immune Sa Compounds for the treatment of diseases associated with amyloid or amyloid-like proteins
US20100144793A1 (en) * 2006-11-24 2010-06-10 Ac Immune Sa Novel compounds for the treatment of diseases associated with amyloid or amyloid-like proteins
US20100183513A1 (en) * 2006-11-24 2010-07-22 Wolfgang Froestl N-(methyl) -1h-pyrazol-3-amine, n-(methyl)-pyridin-2-amine and n-(methyl)-thiazol-2-amine derivatives for the treatment of diseases associated with amyloid or amyloid-like proteins, like e.g. alzheimer's
US8673940B2 (en) 2006-11-24 2014-03-18 Ac Immune Sa Compounds for the treatment of diseases associated with amyloid or amyloid-like proteins
US20110092537A1 (en) * 2009-10-15 2011-04-21 Ac Immune S.A. 2,6-Diaminopyridine Compounds Suitable For Treating Diseases Associated With Amyloid Or Amyloid-Like Proteins Or For Treating Or Preventing Ocular Diseases Or Conditions Associated With A Pathological Abnormality/Change In The Tissue Of The Visual System
US8916590B2 (en) 2009-10-15 2014-12-23 Ac Immune Sa 2,6-diaminopyridine compounds suitable for treating diseases associated with amyloid or amyloid-like proteins or for treating or preventing ocular diseases or conditions associated with a pathological abnormality/change in the tissue of the visual system
US9701660B2 (en) 2009-10-15 2017-07-11 Ac Immune S.A. 2,6-diaminopyridine compounds suitable for treating diseases associated with amyloid or amyloid-like proteins or for treating or preventing ocular diseases or conditions associated with a pathological abnormality/change in the tissue of the visual system
WO2021055388A1 (en) 2019-09-17 2021-03-25 The Lubrizol Corporation 2,5-dimercapto-1,3,4-thiadiazole ("dmtd") derivatives
WO2022046718A1 (en) 2020-08-26 2022-03-03 The Lubrizol Corporation 2,5-dimercapto-1,3,4-thiadiazole (dmtd) zinc salt derivatives
WO2022046625A1 (en) 2020-08-26 2022-03-03 The Lubrizol Corporation 2,5-dimercapto-1,3,4-thiadiazole ("dmtd") metal salt derivatives
CN114805244A (zh) * 2022-05-19 2022-07-29 贵州大学 双-(1,3,4-噻二唑)类衍生物及其制备方法和应用

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GB959661A (en) 1964-06-03
DE1175077B (de) 1964-07-30
BE606550A (en))
CH399903A (de) 1965-09-30
GB940169A (en) 1963-10-23
GB959182A (en) 1964-05-27

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