WO2005025314A1 - Capsaicin derivates and the production and use thereof - Google Patents
Capsaicin derivates and the production and use thereof Download PDFInfo
- Publication number
- WO2005025314A1 WO2005025314A1 PCT/NO2004/000270 NO2004000270W WO2005025314A1 WO 2005025314 A1 WO2005025314 A1 WO 2005025314A1 NO 2004000270 W NO2004000270 W NO 2004000270W WO 2005025314 A1 WO2005025314 A1 WO 2005025314A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- compound
- production
- capsaicin
- paints
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1606—Antifouling paints; Underwater paints characterised by the anti-fouling agent
- C09D5/1612—Non-macromolecular compounds
- C09D5/1625—Non-macromolecular compounds organic
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/22—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
Definitions
- the present invention relates to new compounds, namely cap- saicin derivates, a new method for producing them and their use as micro-organism-repellent agents in paints and coat- ings, especially for marine installations and ships, but also for land-based installations and materials.
- TBT Today tribultin
- Today tribultin (TBT) is used to prevent the growth of algae and sea plants, mussels, sea tulips and similar on ships. Such growth generates friction, which entails a rapid increase in the fuel costs. TBT is therefore added to marine paints in order to produce so-called "antifouling" paints. TBT poisons the marine organisms getting into contact with the substance, and thus keeps the ship's sides free from growt .
- TBT has a number of environmentally negative side effects. TBT does not only affect the marine organisms trying to attach to the sides of the ship, but also poisons other marine life. Further, it has been shown that TBT is ac- cumulated in the marine food chain and leads to unfortunate developments in various organisms. It has been shown, among other things, that TBT leads to deformation of the shell structure in oysters, sex reversal in snails and immunity disturbances as well as neurotoxic and genetic changes in other marine species .
- a new class of compounds can replace TBT as micro-organism-repellent agent.
- the new class of compounds is new derivates of a naturally existing substance, capsaicin, which is an extract from chilli (capsicum annum) and other pepper fruits (capsicum fructus) .
- Capsaicin (E) -8-methyl-N-vanillyl-6-nonenamide) is extracted, as mentioned, from chilli. It is known that this extract has been used as a micro-organism-repellent in marine paints. It also has a number of other useful pharmacological properties as described in, inter alia, Dray, N.S. Biochemical Pharmacology, 44, (1992), 611.
- the capsaicin extract has the following drawbacks, which make it unsuitable as an ingredient in "antifouling paints" .
- the standardized capsaicin extract contains at least 3 isomers, which all have different chemical properties but which are difficult to differentiate between. It may therefore be difficult to obtain capsaicin extracts which have sufficiently uniform purity and composition for the intended use.
- modern marine paints are based on a chemical bonding of a repellent to a polymer base in order to prevent the repellent from being washed into the sea water immediately. The repellent, bonded to the polymer base, is liberated in step with the sea water's reacting with the polymer base. The less hydrophilic the repellent is, the longer life the marine paint will have.
- Natural capsaicin extracts consist of several isomers of different chemical properties and the water solubility of these isomers varies with the pH-value of the water. This will give an unwanted and non-controllable variation in the solubility properties of repellent products based on natural capsaicin extracts .
- US patent 5,629,045 also describes an antifouling paint containing, inter alia, capsaicin and vanillylamide derivates with alkyl substitu- ents, as the active ingredient.
- the production of the va- nillylamide derivates is based on extracts of capsaicin.
- the paint of US patent 5,698,191 also contains a capsaicin oleoresin in combination with a saponin compound. It is an object of the present invention to provide an alternative to TBT, which is not poisonous and does not accumulate in the marine food chain.
- new chemical compounds are now provided, namely new capsaicin alkyne analogues which may be called phenylcapsaicin.
- the new chemical compounds according to the invention are characterized by the general formula (1) ,
- R is a substituent selected from the group of alkyl, alkenyl, alkynyl, allyl, aryl, alkoxy, aryloxy, alkanoyl, aroyl, a ino, alkylthio, arylthio, cyano, cycloalkyl, cyclo- alkenyl, halo, hydroxy, oxo, nitro, trifluoromethyl; when said substituent R contains a carbon chain, it may be straight-chained or branched and possibly further substituted with alkyl, alkenyl, alkynyl, allyl, aryl, alkoxy, aryloxy, alkanoyl, aroyl, amino, alkylthio, arylthio, cyano, cycloal- kyl, cycloalkenyl, halo, hydroxy, oxo, nitro, trifluoromethyl .
- R contains a carbon chain
- this carbon chain has from 1 to 8 carbon atoms, more preferably from 2 to 6 carbon atoms.
- Another group of preferred formula (1) compounds are those having carbon chains in R that are 1-4 carbon atoms long.
- R is an alkyl with 1-4 carbon atoms
- the most pre- ferred compounds are those, in which R is isopropyl or pro- pyl.
- the formula (1) compounds can generally be produced by converting a carboxylic acid derivate (3) or a carboxylic acid, that is Z is HO, with a vanillylamine (2) for producing a capsaicin derivate with the formula (1) , as appears from the following reaction diagram A:
- R is a substituent selected from the group of alkyl, alkenyl, alkynyl, allyl, aryl, alkoxy, aryloxy, alkanoyl, aroyl, amino, alkylthio, arylthio, cyano, cycloalkyl, cycloalkenyl, halo, hydroxy, oxo, nitro, trifluoromethyl; when said substituent R contains a carbon chain, it may be straight- chained or branched, and possibly further substituted with alkyl, alkenyl, alkynyl, allyl, aryl, alkoxy, aryloxy, alkanoyl, aroyl, amino, alkylthio, arylthio, cyano, cycloalkyl, cycloalkenyl, halo, hydroxy, oxo, nitro, trifluoromethyl
- the carboxylic acid derivate (3) is meant to include any suitable reactant for the reaction shown in reaction diagram A and may most preferably be an ester, an amide or an acid chloride.
- the term “carboxylic acid derivate (3)" is also meant to include the carboxylic acid (4) itself.
- the vanillylamine compound (2) from vanillin can be produced as described in Kaga, H., Miura, M. and Kazuhiko, O., J. Org. Chem. 54 (1989) 3477. A yield of 42 % was achieved.
- the other reactant, compound (3) or (4) can be produced through the following steps: converting an acetylene compound (8) with a protected 5- chloro-1-pentanol (7) for the production of a protected acetylene alcohol compound (6) ; decomposing the protective group from the compound (6) to produce the free acetylene alcohol compound (5) ; oxidizing the compound (5) for the production of the carbox- ylic acid (4) ; and possibly transferring the acid (4) to the carboxylic acid chloride (3) .
- R is a substituent selected from the group of alkyl, alkenyl, alkynyl, allyl, aryl, alkoxy, aryloxy, alkanoyl, aroyl, amino, alkylthio, arylthio, cyano, cycloalkyl, cycloalkenyl, halo, hydroxy, oxo, nitro, trifluoromethyl; when said substituent R contains a carbon chain, it may be straight-chained or branched, and possibly further substituted with alkyl, alkenyl, alkynyl, allyl, aryl, alkoxy, aryloxy, alkanoyl, aroyl, amino, alkylthio, arylthio, cyano, cycloalkyl, cycloalkenyl, halo, hydroxy, oxo, nitro, trifluoromethyl .
- the new capsaicin alkyne analogues with the formula (1) may be used, in one embodiment of the invention, as a microorganism-repellent agent.
- This micro-organism-repellent agent can, either alone or as an ingredient in a micro-organism- repellent mixture, be included in paints or coatings to produce end products that prevent the growth of micro-organisms and other living organisms on the surface, to which the end product is applied.
- Said agent or mixture can be added to a paint or a coating, so that the active formula (1) compound is present in a concentration of 0,1-50 % by weight, in particular in a concentration of 0,2-10 % by weight. It is preferred the most to add a formula (1) compound to a paint or coating in a concentration of 0,5-5 % by weight, in particular 0,3-1 % by ⁇ weight .
- One embodiment of the invention is a micro-organism repellent agent including a combination of two or more formula (1) compounds .
- Another embodiment of the invention is a micro-organism- repellent agent including a combination of a formula (1) compound and another micro-organism-repellent agent.
- Another embodiment of the invention is a micro-organism- repellent mixture, in which a formula (1) compound is included in a mixture with one or more inert additives, such as solvents, consistency modifiers, i.e. thinners or thickeners; and/or preservatives .
- a paint or coating to which a micro-organism-repellent agent or mixture according to the invention has been added in order to prevent the growth of micro-organisms or other small organisms, like seashells, algae, sea tulips, sea plants and fungi.
- Such a paint referred to as “antifouling” paint
- a micro-organism- repellent agent or mixture according to the invention in a coating which may be applied, for example, over a coat of paint in order to form a watertight surface or a surface with other desired properties .
- Yet another embodiment of the invention is a paint or a coat- ing corresponding to that described above for land-based installations and structures, in particular of the kinds based on wood, such as timber, wooden panels and similar.
- capsaicin has the described biological activity and effect according to the invention.
- capsaicin and/or other formula (1) compounds could achieve other activities in the concentrations used in this experiment.
- Capsaicin is mixed into a commercially available ship-bottom paint that has been declared free of biocides .
- the paint has the trade mark Fabio EcoTM and is produced by International Paint, Akzo-Nobel. 3 different concentrations were made with 0 g, 1 g and 5 g of capsaicin per kg of paint.
- Capsaicin was first dissolved in 10 ml of a thinner (International No. 3) and then mixed into the paint. A mixture of just Fabio Eco and 10 ml of thinner was used as a control. The paint mixture was allowed to rest for 1 hour before application. The paint was applied to a number of plexiglass panels (11 x 11 x 0,2 cm) .
- the painted panels were left to dry for 24 hours at 21 °C as prescribed by the producer.
- the panels were mounted onto an aluminium frame and put out 0,5-1 m below the sea surface on a test raft.
- the test raft was placed outside a marine biology laboratory with a water depth of 10 m.
- the panels were left for a period from 4th July 2001 to 31st August 2001. This period is the most growth-intensive period for marine organisms on a ship's hull and first of all for the sea tulip Balanus improvisus. The panels were then retrieved for immediate analysis . Analysis of Growth
- the following analyses of the panels were carried out : The panels were photographed. Coverage of the sea tulip Balanus improvisus was evaluated. Coverage of the blue mussel Mytilus edulis was evaluated. All growth on the panel was scraped off and the wet weight was determined.
- Figure 1 shows in a bar chart the coverage of the sea tulip Balanus improvisus with the 3 different surface treatments, The bars denote mean values and standard deviations for 5 repetitions.
- Figure 2 shows the coverage of the blue mussel Mytilus edulis, in a corresponding way to that described for Figure 1.
- the bars denote mean values and standard deviations for 5 repetitions . As appears from this bar chart, there is no statistically significant difference between the 3 treatments (1-factor analysis of variance, p>0,05).
- Figure 3 shows the wet weight of the total growth on the pan- els for the three different treatments.
- the bars denote mean values and standard deviations for 5 repetitions .
- Figure 4 shows pictures of the five surfaces treated with the control paint (0 g/kg) .
- Figure 5 shows pictures of the five surfaces treated with the lowest concentration of 1 g/kg.
- Figure 6 shows pictures of the five surfaces treated with the highest concentration of 5 g/kg. By optical comparison it can be seen clearly that the surfaces in Figure 6 have considerably less growth than the control surfaces.
- the aqueous phase was extracted with petroleum ether (boiling point 40-60 °C) /Et ⁇ O 1:1 (5 x 50 mL) .
- the combined organic phases were washed with water (2 x 20 mL) and dried (MgS ⁇ 4) . Distillation on a rotary evaporator yielded 9,1 g (97 %) of a yellow viscous oil. TLC and NMR indicated a pure product .
- 7-phenylhept-6-yne acid (5) Brown's chromic acid reagent (133 mL, 88 mmol, 0,66 M) was added slowly in drops to a magnetically stirred solution of 7-phenylhept-6-yn-l-ol (6) (7,53 g, 40 mmol) in acetone (400 mL) at 0 °C. After the chromic acid had been added, the reaction mixture was stirred for 1 hour at 0 °C and then at room temperature until all the base material has been converted as indicated by TLC.
- Vanillylamine was synthesized on a 100 mmol scale as described in the literature. 6
Abstract
Description
Claims
Priority Applications (15)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP04775054A EP1670310B1 (en) | 2003-09-12 | 2004-09-10 | Capsaicin derivates and the production and use thereof |
DK04775054T DK1670310T3 (en) | 2003-09-12 | 2004-09-10 | Capsaicin derivatives and their preparation and use |
BRPI0414280-2A BRPI0414280B1 (en) | 2003-09-12 | 2004-09-10 | CAPSAICINE-DERIVED CHEMICAL COMPOUND, USE AND METHOD FOR THE SAME PRODUCTION |
US10/571,658 US7446226B2 (en) | 2003-09-12 | 2004-09-10 | Capsaicin derivates and the production and use thereof |
KR1020067005093A KR101116121B1 (en) | 2003-09-12 | 2004-09-10 | Capsaicin derivates and the production and use thereof |
DE602004010164T DE602004010164T2 (en) | 2003-09-12 | 2004-09-10 | CAPSAICIN DERIVATIVES AND THEIR PRODUCTION AND USE |
PL04775054T PL1670310T3 (en) | 2003-09-12 | 2004-09-10 | Capsaicin derivates and the production and use thereof |
JP2006526038A JP4533383B2 (en) | 2003-09-12 | 2004-09-10 | Capsaicin derivatives and their production and use |
AU2004271873A AU2004271873B2 (en) | 2003-09-12 | 2004-09-10 | Capsaicin derivates and the production and use thereof |
NZ545537A NZ545537A (en) | 2003-09-12 | 2004-09-10 | Capsaicin derivates and the production and use thereof |
NO20060834A NO334592B1 (en) | 2003-09-12 | 2006-02-21 | Capsaicin derivatives, their preparation and use, as well as paints and coatings comprising these. |
IL173981A IL173981A (en) | 2003-09-12 | 2006-02-27 | Capsaicin derivatives and the production and use thereof |
EGNA2006000227 EG25674A (en) | 2003-09-12 | 2006-03-08 | Method for producing of capsaicin as a micro |
HK07102406.7A HK1095065A1 (en) | 2003-09-12 | 2007-03-05 | Capsaicin derivates and the production and use thereof |
HR20080063T HRP20080063T3 (en) | 2003-09-12 | 2008-02-11 | Capsaicin derivates and the production and use thereof |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NO20034069A NO20034069L (en) | 2003-09-12 | 2003-09-12 | Preparation and use of capsaicin derivatives |
NO20034069 | 2003-09-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2005025314A1 true WO2005025314A1 (en) | 2005-03-24 |
Family
ID=29245032
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/NO2004/000270 WO2005025314A1 (en) | 2003-09-12 | 2004-09-10 | Capsaicin derivates and the production and use thereof |
Country Status (23)
Country | Link |
---|---|
US (1) | US7446226B2 (en) |
EP (1) | EP1670310B1 (en) |
JP (1) | JP4533383B2 (en) |
KR (1) | KR101116121B1 (en) |
CN (1) | CN100415095C (en) |
AT (1) | ATE377947T1 (en) |
AU (1) | AU2004271873B2 (en) |
BR (1) | BRPI0414280B1 (en) |
CY (1) | CY1107884T1 (en) |
DE (1) | DE602004010164T2 (en) |
DK (1) | DK1670310T3 (en) |
EG (1) | EG25674A (en) |
ES (1) | ES2297477T3 (en) |
HK (1) | HK1095065A1 (en) |
HR (1) | HRP20080063T3 (en) |
IL (1) | IL173981A (en) |
MY (1) | MY141744A (en) |
NO (2) | NO20034069L (en) |
NZ (1) | NZ545537A (en) |
PL (1) | PL1670310T3 (en) |
PT (1) | PT1670310E (en) |
TW (1) | TWI358433B (en) |
WO (1) | WO2005025314A1 (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102008006430A1 (en) | 2008-01-28 | 2009-08-06 | Florian Galow | Beverage recipe for a drink with a specific water portion and a flavorful stimulatory essence, which contains a capsaicinoid and has a specific severity level |
BE1019713A3 (en) * | 2010-12-24 | 2012-10-02 | Axichem Ab | REPELLENT PAINTING BASED ON CAPSAICIN DERIVATIVES. |
CN103288665A (en) * | 2013-06-27 | 2013-09-11 | 上海化学试剂研究所有限公司 | Preparation method of capsaicine |
US8575230B2 (en) | 2007-04-19 | 2013-11-05 | University Of North Texas Health Science Center At Fort Worth | Environment-friendly antifoulants for the prevention of biofouling |
WO2017061871A1 (en) | 2015-10-09 | 2017-04-13 | Axichem Ab | Bird feed and in particular poultry feed, comprising synthetic capsaicinoid derivatives and such feed for prohylactic use or treatment of salmonella infection |
WO2017160165A1 (en) * | 2016-03-18 | 2017-09-21 | Axichem Ab | Synthetic capsaicinoid derivatives and feed comprising such compounds as growth promotors |
US11471429B2 (en) | 2017-10-20 | 2022-10-18 | Axichem Ab | Synthetic capsaicin analogues as bioenhancers |
WO2022253884A1 (en) * | 2021-06-02 | 2022-12-08 | Axichem Ab | Capsaicin derivatives in the treatment of idiopathic pulmonary fibrosis |
EP4121408A4 (en) * | 2020-03-20 | 2024-04-24 | Axichem Ab | Synthesis of capsaicin derivatives |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010059292A (en) * | 2008-09-02 | 2010-03-18 | Shokichi Inami | Ship bottom paint and method for manufacturing the same |
WO2011006073A1 (en) | 2009-07-10 | 2011-01-13 | President And Fellows Of Harvard College | Permanently charged sodium and calcium channel blockers as anti-inflammatory agents |
CN102040507B (en) * | 2009-10-10 | 2013-12-04 | 台州市华南医化有限公司 | Preparation methods of 7-phenyl-6-heptynoic acid and reactant of sodium 5-bromo-pentanoate |
EP2629610B1 (en) | 2010-07-27 | 2017-09-06 | Flex Pharma, Inc. | Methods and compositions for preventing and relieving muscle cramps and for recovery from neuromuscular irritability and fatigue following exercise |
CN102060689B (en) * | 2010-12-14 | 2013-05-08 | 台州市华南医化有限公司 | Synthetic method of phenyl capsaicin midbody 7-phenyl-6-heptynoic acid |
WO2012086811A1 (en) | 2010-12-22 | 2012-06-28 | 味の素株式会社 | Food intake suppressant and anti-obesity agent |
CN106458854A (en) * | 2014-03-27 | 2017-02-22 | 有机燃料瑞典公司 | Efficient synthesis of amines and amides from alcohols and aldehydes by using cascade catalysis |
CN104370985B (en) * | 2014-09-30 | 2020-04-28 | 上海化学试剂研究所有限公司 | Capsaicinoid compound as well as preparation method and application thereof |
CN104927585B (en) * | 2015-07-13 | 2018-10-16 | 上海金泛斯标识有限公司 | Luminous paint for jet-printed advertisements |
AU2016301282B2 (en) | 2015-08-03 | 2022-03-17 | Children's Medical Center Corporation | Charged ion channel blockers and methods for use |
US11253493B2 (en) | 2017-01-23 | 2022-02-22 | Cliff-Cartwright Corporation | Compositions and methods affecting exercise performance |
CN108947863B (en) * | 2018-06-12 | 2021-04-30 | 上海博志研新药物技术有限公司 | Preparation method of nucesin and intermediate thereof |
US10780083B1 (en) | 2019-03-11 | 2020-09-22 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
US10828287B2 (en) | 2019-03-11 | 2020-11-10 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
MA55320A (en) | 2019-03-11 | 2022-01-19 | Nocion Therapeutics Inc | ESTER SUBSTITUTED ION CHANNEL BLOCKERS AND METHODS OF USE |
EP3937945A4 (en) | 2019-03-11 | 2023-01-04 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
JP2022527690A (en) | 2019-03-11 | 2022-06-03 | ノシオン セラピューティクス,インコーポレイテッド | Charged ion channel blockers and usage |
WO2021014395A1 (en) * | 2019-07-24 | 2021-01-28 | Dr. Reddy’S Institute Of Life Sciences | Process for the synthesis of deuterated capsaicin, capsaicinoids and synthetic capsaicin analogs |
US10933055B1 (en) | 2019-11-06 | 2021-03-02 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
CN114828845A (en) | 2019-11-06 | 2022-07-29 | 诺西恩医疗公司 | Charged ion channel blockers and methods of use thereof |
JP2023517604A (en) | 2020-03-11 | 2023-04-26 | ノシオン セラピューティクス,インコーポレイテッド | Charged ion channel blockers and methods of use |
NO346665B1 (en) * | 2020-11-17 | 2022-11-21 | Axichem Ab | Capsaicyns in the treatment of leaky gut |
NO20220225A1 (en) | 2022-02-18 | 2023-08-21 | Axichem Ab | Bioenhancers |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04208207A (en) * | 1990-09-14 | 1992-07-29 | Nippon Kayaku Co Ltd | Termite-controlling agent |
JPH069308A (en) * | 1992-06-19 | 1994-01-18 | Nippon Kayaku Co Ltd | Production of synthetic capsaicin and its microcapsule agent in the same reactor |
JPH0680850A (en) * | 1992-09-03 | 1994-03-22 | Nippon Kayaku Co Ltd | Thermoplastic resin composition for preventing animal-biting damage and its production |
US5397385A (en) * | 1994-03-28 | 1995-03-14 | Watts; James L. | Anti-fouling coating composition containing capsaicin |
JPH09100202A (en) * | 1995-10-03 | 1997-04-15 | Meiji Milk Prod Co Ltd | Anti-organism agent |
US5629045A (en) * | 1992-09-17 | 1997-05-13 | Richard L. Veech | Biodegradable nosiogenic agents for control of non-vertebrate pests |
-
2003
- 2003-09-12 NO NO20034069A patent/NO20034069L/en not_active Application Discontinuation
-
2004
- 2004-09-03 TW TW093126656A patent/TWI358433B/en active
- 2004-09-08 MY MYPI20043640A patent/MY141744A/en unknown
- 2004-09-10 DE DE602004010164T patent/DE602004010164T2/en active Active
- 2004-09-10 WO PCT/NO2004/000270 patent/WO2005025314A1/en active IP Right Grant
- 2004-09-10 ES ES04775054T patent/ES2297477T3/en active Active
- 2004-09-10 JP JP2006526038A patent/JP4533383B2/en active Active
- 2004-09-10 AT AT04775054T patent/ATE377947T1/en active
- 2004-09-10 EP EP04775054A patent/EP1670310B1/en active Active
- 2004-09-10 CN CNB2004800260925A patent/CN100415095C/en active Active
- 2004-09-10 PL PL04775054T patent/PL1670310T3/en unknown
- 2004-09-10 PT PT04775054T patent/PT1670310E/en unknown
- 2004-09-10 KR KR1020067005093A patent/KR101116121B1/en active IP Right Grant
- 2004-09-10 US US10/571,658 patent/US7446226B2/en active Active
- 2004-09-10 NZ NZ545537A patent/NZ545537A/en unknown
- 2004-09-10 BR BRPI0414280-2A patent/BRPI0414280B1/en active IP Right Grant
- 2004-09-10 DK DK04775054T patent/DK1670310T3/en active
- 2004-09-10 AU AU2004271873A patent/AU2004271873B2/en active Active
-
2006
- 2006-02-21 NO NO20060834A patent/NO334592B1/en unknown
- 2006-02-27 IL IL173981A patent/IL173981A/en active IP Right Grant
- 2006-03-08 EG EGNA2006000227 patent/EG25674A/en active
-
2007
- 2007-03-05 HK HK07102406.7A patent/HK1095065A1/en unknown
-
2008
- 2008-02-11 HR HR20080063T patent/HRP20080063T3/en unknown
- 2008-02-13 CY CY20081100165T patent/CY1107884T1/en unknown
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04208207A (en) * | 1990-09-14 | 1992-07-29 | Nippon Kayaku Co Ltd | Termite-controlling agent |
JPH069308A (en) * | 1992-06-19 | 1994-01-18 | Nippon Kayaku Co Ltd | Production of synthetic capsaicin and its microcapsule agent in the same reactor |
JPH0680850A (en) * | 1992-09-03 | 1994-03-22 | Nippon Kayaku Co Ltd | Thermoplastic resin composition for preventing animal-biting damage and its production |
US5629045A (en) * | 1992-09-17 | 1997-05-13 | Richard L. Veech | Biodegradable nosiogenic agents for control of non-vertebrate pests |
US5397385A (en) * | 1994-03-28 | 1995-03-14 | Watts; James L. | Anti-fouling coating composition containing capsaicin |
JPH09100202A (en) * | 1995-10-03 | 1997-04-15 | Meiji Milk Prod Co Ltd | Anti-organism agent |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8575230B2 (en) | 2007-04-19 | 2013-11-05 | University Of North Texas Health Science Center At Fort Worth | Environment-friendly antifoulants for the prevention of biofouling |
US8895637B2 (en) | 2007-04-19 | 2014-11-25 | University Of North Texas Health Science Center At Fort Worth | Environment-friendly antifoulants for the prevention of biofouling |
DE102008006430A1 (en) | 2008-01-28 | 2009-08-06 | Florian Galow | Beverage recipe for a drink with a specific water portion and a flavorful stimulatory essence, which contains a capsaicinoid and has a specific severity level |
BE1019713A3 (en) * | 2010-12-24 | 2012-10-02 | Axichem Ab | REPELLENT PAINTING BASED ON CAPSAICIN DERIVATIVES. |
CN103288665A (en) * | 2013-06-27 | 2013-09-11 | 上海化学试剂研究所有限公司 | Preparation method of capsaicine |
WO2017061871A1 (en) | 2015-10-09 | 2017-04-13 | Axichem Ab | Bird feed and in particular poultry feed, comprising synthetic capsaicinoid derivatives and such feed for prohylactic use or treatment of salmonella infection |
WO2017160165A1 (en) * | 2016-03-18 | 2017-09-21 | Axichem Ab | Synthetic capsaicinoid derivatives and feed comprising such compounds as growth promotors |
US11471429B2 (en) | 2017-10-20 | 2022-10-18 | Axichem Ab | Synthetic capsaicin analogues as bioenhancers |
EP4121408A4 (en) * | 2020-03-20 | 2024-04-24 | Axichem Ab | Synthesis of capsaicin derivatives |
WO2022253884A1 (en) * | 2021-06-02 | 2022-12-08 | Axichem Ab | Capsaicin derivatives in the treatment of idiopathic pulmonary fibrosis |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP1670310B1 (en) | Capsaicin derivates and the production and use thereof | |
KR20060136361A (en) | Capsaicin derivates and the production and use thereof | |
Bazes et al. | Investigation of the antifouling constituents from the brown alga Sargassum muticum (Yendo) Fensholt | |
US20080095737A1 (en) | Non-toxic coating composition, methods of use thereof and articles protected from attachment of biofouling organisms | |
Escobar et al. | Alkyl 2-furoates obtained by green chemistry procedures as suitable new antifoulants for marine protective coatings | |
US20160311788A1 (en) | Antifouling Compounds And Use Thereof | |
US8177896B2 (en) | Antifouling furan-2-one derivatives | |
AU2001275527A1 (en) | Non-toxic coating composition, methods of use thereof and articles protected from attachment of biofouling organisms | |
NZ542883A (en) | Non-toxic coating composition, methods of use thereof and articles protected from attachment of biofouling organisms | |
MXPA06002617A (en) | Capsaicin derivates and the production and use thereof | |
JPS6341495A (en) | Polycyclic terpenoid glycoside and antifouling paint for repelling sticking of aquatic organism containing said glycoside | |
US20020022044A1 (en) | Non-toxic coating composition, methods of use thereof and articles protected from attachment of biofouling organisms | |
WO1998039289A1 (en) | Urea derivatives, and industrial antibacterial and antifungal agents, algaecides and antiperiphytic agents containing the same | |
JPH1171212A (en) | Industrial antibacterial/antifungal agent, algicide and anti-biofouling agent each containing thiadiazoleurea compound |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 200480026092.5 Country of ref document: CN |
|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BW BY BZ CA CH CN CO CR CU CZ DK DM DZ EC EE EG ES FI GB GD GE GM HR HU ID IL IN IS JP KE KG KP KZ LC LK LR LS LT LU LV MA MD MK MN MW MX MZ NA NI NO NZ PG PH PL PT RO RU SC SD SE SG SK SY TJ TM TN TR TT TZ UA UG US UZ VN YU ZA ZM |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): GM KE LS MW MZ NA SD SZ TZ UG ZM ZW AM AZ BY KG MD RU TJ TM AT BE BG CH CY DE DK EE ES FI FR GB GR HU IE IT MC NL PL PT RO SE SI SK TR BF CF CG CI CM GA GN GQ GW ML MR SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 12006500394 Country of ref document: PH |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2006526038 Country of ref document: JP Ref document number: 545537 Country of ref document: NZ |
|
WWE | Wipo information: entry into national phase |
Ref document number: 173981 Country of ref document: IL |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2004271873 Country of ref document: AU |
|
WWE | Wipo information: entry into national phase |
Ref document number: PA/a/2006/002617 Country of ref document: MX |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1020067005093 Country of ref document: KR |
|
ENP | Entry into the national phase |
Ref document number: 2004271873 Country of ref document: AU Date of ref document: 20040910 Kind code of ref document: A |
|
WWP | Wipo information: published in national office |
Ref document number: 2004271873 Country of ref document: AU |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2004775054 Country of ref document: EP Ref document number: 1200600579 Country of ref document: VN |
|
DPEN | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed from 20040101) | ||
WWP | Wipo information: published in national office |
Ref document number: 2004775054 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref document number: PI0414280 Country of ref document: BR |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2007167524 Country of ref document: US Ref document number: 10571658 Country of ref document: US |
|
WWP | Wipo information: published in national office |
Ref document number: 1020067005093 Country of ref document: KR |
|
WWP | Wipo information: published in national office |
Ref document number: 10571658 Country of ref document: US |
|
WWG | Wipo information: grant in national office |
Ref document number: 2004775054 Country of ref document: EP |