AU2005251975B2 - Monomer 5,6-diphenyl-1,2,4-triazinic derivatives and the use thereof - Google Patents
Monomer 5,6-diphenyl-1,2,4-triazinic derivatives and the use thereof Download PDFInfo
- Publication number
- AU2005251975B2 AU2005251975B2 AU2005251975A AU2005251975A AU2005251975B2 AU 2005251975 B2 AU2005251975 B2 AU 2005251975B2 AU 2005251975 A AU2005251975 A AU 2005251975A AU 2005251975 A AU2005251975 A AU 2005251975A AU 2005251975 B2 AU2005251975 B2 AU 2005251975B2
- Authority
- AU
- Australia
- Prior art keywords
- diphenyl
- triazine
- compounds
- group
- bis
- 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.)
- Ceased
Links
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- 239000000203 mixture Substances 0.000 claims abstract description 44
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- 239000003223 protective agent Substances 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 239000012634 fragment Substances 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- -1 poly(ethoxy) Polymers 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
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- 238000006467 substitution reaction Methods 0.000 claims abstract description 3
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- MBAZYZCVSWUMMY-UHFFFAOYSA-N 3-(4-dodecoxyphenyl)-5,6-bis(4-methoxyphenyl)-1,2,4-triazine Chemical compound C1=CC(OCCCCCCCCCCCC)=CC=C1C(N=C1C=2C=CC(OC)=CC=2)=NN=C1C1=CC=C(OC)C=C1 MBAZYZCVSWUMMY-UHFFFAOYSA-N 0.000 claims description 3
- DCRHKNARVXSYDJ-UHFFFAOYSA-N 3-(5,6-diphenyl-1,2,4-triazin-3-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2N=C(C(C=3C=CC=CC=3)=NN=2)C=2C=CC=CC=2)=C1 DCRHKNARVXSYDJ-UHFFFAOYSA-N 0.000 claims description 3
- ACYYHTVUQOCIIQ-UHFFFAOYSA-N 3-[5,6-bis(4-methoxyphenyl)-1,2,4-triazin-3-yl]benzonitrile Chemical compound C1=CC(OC)=CC=C1C1=NN=C(C=2C=C(C=CC=2)C#N)N=C1C1=CC=C(OC)C=C1 ACYYHTVUQOCIIQ-UHFFFAOYSA-N 0.000 claims description 3
- SNKXPBVLPJFKRY-UHFFFAOYSA-N 4-[5,6-bis(4-methoxyphenyl)-1,2,4-triazin-3-yl]benzonitrile Chemical compound C1=CC(OC)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C#N)N=C1C1=CC=C(OC)C=C1 SNKXPBVLPJFKRY-UHFFFAOYSA-N 0.000 claims description 3
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- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 description 15
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- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 4
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- 239000012752 auxiliary agent Substances 0.000 description 1
- BHXFKXOIODIUJO-UHFFFAOYSA-N benzene-1,4-dicarbonitrile Chemical compound N#CC1=CC=C(C#N)C=C1 BHXFKXOIODIUJO-UHFFFAOYSA-N 0.000 description 1
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N benzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical class C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 125000006182 dimethyl benzyl group Chemical group 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- DLAHAXOYRFRPFQ-UHFFFAOYSA-N dodecyl benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1 DLAHAXOYRFRPFQ-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 1
- PMMXXYHTOMKOAZ-UHFFFAOYSA-N hexadecyl 7-methyloctanoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)CCCCCC(C)C PMMXXYHTOMKOAZ-UHFFFAOYSA-N 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 230000003061 melanogenesis Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- BIWCGHBVOIMOJS-UHFFFAOYSA-N n'-amino-4-cyanobenzenecarboximidamide Chemical compound NN=C(N)C1=CC=C(C#N)C=C1 BIWCGHBVOIMOJS-UHFFFAOYSA-N 0.000 description 1
- LHTGBZMVHWJBQB-UHFFFAOYSA-N n,2-diethylaniline Chemical compound CCNC1=CC=CC=C1CC LHTGBZMVHWJBQB-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- YBGZDTIWKVFICR-UHFFFAOYSA-N octinoxate Chemical compound CCCCC(CC)COC(=O)C=CC1=CC=C(OC)C=C1 YBGZDTIWKVFICR-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 231100000760 phototoxic Toxicity 0.000 description 1
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 230000037307 sensitive skin Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005437 stratosphere Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4966—Triazines or their condensed derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0404810A FR2869906B1 (fr) | 2004-05-05 | 2004-05-05 | Derives monomeriques de 5,6-diphenyl-1,2,4-triazine et leurs utilisations |
| FR0404810 | 2004-05-05 | ||
| PCT/FR2005/001129 WO2005121108A1 (fr) | 2004-05-05 | 2005-05-04 | Derives monomeriques de 5,6-diphenyl-1,2,4-triazine et leurs utilisations |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2005251975A1 AU2005251975A1 (en) | 2005-12-22 |
| AU2005251975B2 true AU2005251975B2 (en) | 2011-10-13 |
Family
ID=34945753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2005251975A Ceased AU2005251975B2 (en) | 2004-05-05 | 2005-05-04 | Monomer 5,6-diphenyl-1,2,4-triazinic derivatives and the use thereof |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8053573B2 (https=) |
| EP (1) | EP1751122B1 (https=) |
| JP (1) | JP5091665B2 (https=) |
| AT (1) | ATE461180T1 (https=) |
| AU (1) | AU2005251975B2 (https=) |
| CA (1) | CA2564493C (https=) |
| DE (1) | DE602005019995D1 (https=) |
| ES (1) | ES2341558T3 (https=) |
| FR (1) | FR2869906B1 (https=) |
| WO (1) | WO2005121108A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010056914A1 (en) * | 2008-11-12 | 2010-05-20 | Microbiotix, Inc. | Bacterial helicase inhibitor compounds and uses thereof |
| SI2531492T1 (sl) | 2010-02-05 | 2016-08-31 | Heptares Therapeutics Limited | Derivati 1,2,4-triazin-4-amina |
| JP2011207804A (ja) * | 2010-03-29 | 2011-10-20 | Fujifilm Corp | 外用剤組成物 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3130046A (en) * | 1959-01-07 | 1964-04-21 | Azoplate Corp | Electrophotographic reproduction material |
| US3211729A (en) * | 1961-03-28 | 1965-10-12 | Ciba Ltd | 1:2:4-triazine compounds |
| US3948894A (en) * | 1974-01-31 | 1976-04-06 | Eli Lilly And Company | 3-Amino-5,6-diaryl-1,2,4-triazines |
| US3989831A (en) * | 1974-01-31 | 1976-11-02 | Eli Lilly And Company | Topically-active anti-inflammatory 3-chloro-5,6-diaryl-1,2,4-triazines |
| US4008232A (en) * | 1975-06-23 | 1977-02-15 | Eli Lilly And Company | 3-Amino-5,6-diaryl-1,2,4-triazines |
| FR2477873A1 (fr) * | 1980-03-17 | 1981-09-18 | Fabre Sa Pierre | Nouveaux filtres solaires et composition les contenant |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3979516A (en) * | 1974-01-31 | 1976-09-07 | Eli Lilly And Company | Anti-inflammatory 3-amino-5,6-diaryl-1,2,4-triazines |
| FR2485531A1 (fr) * | 1980-06-25 | 1981-12-31 | Fabre Sa Pierre | Nouveaux n-oxydes de diaryl-5,6 as triazines 1-2-4, leur application a titre de medicaments et les compositions pharmaceutiques les contenant |
| DD247899A1 (de) * | 1984-03-09 | 1987-07-22 | Univ Ernst Moritz Arndt | Verfahren zur synthese von 5,6-disubstituierten 1,2,4-triazinen |
| JP2000258903A (ja) * | 1999-03-11 | 2000-09-22 | Konica Corp | 特定化合物、それを用いた感光性組成物、画像形成材料及び画像形成方法 |
| FR2803194A1 (fr) | 2000-01-03 | 2001-07-06 | Oreal | Nouveaux derives de s-triazine, leur procede de preparation, compositions les contenant et leurs utilisations |
-
2004
- 2004-05-05 FR FR0404810A patent/FR2869906B1/fr not_active Expired - Fee Related
-
2005
- 2005-05-04 CA CA2564493A patent/CA2564493C/fr not_active Expired - Lifetime
- 2005-05-04 AU AU2005251975A patent/AU2005251975B2/en not_active Ceased
- 2005-05-04 ES ES05769413T patent/ES2341558T3/es not_active Expired - Lifetime
- 2005-05-04 US US11/579,341 patent/US8053573B2/en active Active
- 2005-05-04 DE DE602005019995T patent/DE602005019995D1/de not_active Expired - Lifetime
- 2005-05-04 AT AT05769413T patent/ATE461180T1/de not_active IP Right Cessation
- 2005-05-04 WO PCT/FR2005/001129 patent/WO2005121108A1/fr not_active Ceased
- 2005-05-04 EP EP05769413A patent/EP1751122B1/fr not_active Expired - Lifetime
- 2005-05-04 JP JP2007512266A patent/JP5091665B2/ja not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3130046A (en) * | 1959-01-07 | 1964-04-21 | Azoplate Corp | Electrophotographic reproduction material |
| US3211729A (en) * | 1961-03-28 | 1965-10-12 | Ciba Ltd | 1:2:4-triazine compounds |
| US3948894A (en) * | 1974-01-31 | 1976-04-06 | Eli Lilly And Company | 3-Amino-5,6-diaryl-1,2,4-triazines |
| US3989831A (en) * | 1974-01-31 | 1976-11-02 | Eli Lilly And Company | Topically-active anti-inflammatory 3-chloro-5,6-diaryl-1,2,4-triazines |
| US4008232A (en) * | 1975-06-23 | 1977-02-15 | Eli Lilly And Company | 3-Amino-5,6-diaryl-1,2,4-triazines |
| FR2477873A1 (fr) * | 1980-03-17 | 1981-09-18 | Fabre Sa Pierre | Nouveaux filtres solaires et composition les contenant |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005121108A1 (fr) | 2005-12-22 |
| DE602005019995D1 (de) | 2010-04-29 |
| ES2341558T3 (es) | 2010-06-22 |
| CA2564493C (fr) | 2012-10-23 |
| EP1751122B1 (fr) | 2010-03-17 |
| JP2007536353A (ja) | 2007-12-13 |
| US8053573B2 (en) | 2011-11-08 |
| ATE461180T1 (de) | 2010-04-15 |
| US20080299055A1 (en) | 2008-12-04 |
| FR2869906A1 (fr) | 2005-11-11 |
| CA2564493A1 (fr) | 2005-12-22 |
| AU2005251975A1 (en) | 2005-12-22 |
| JP5091665B2 (ja) | 2012-12-05 |
| FR2869906B1 (fr) | 2006-08-11 |
| EP1751122A1 (fr) | 2007-02-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |