DE2201968A1 - Entzuendungshemmer fuer kosmetische praeparationen - Google Patents
Entzuendungshemmer fuer kosmetische praeparationenInfo
- Publication number
- DE2201968A1 DE2201968A1 DE19722201968 DE2201968A DE2201968A1 DE 2201968 A1 DE2201968 A1 DE 2201968A1 DE 19722201968 DE19722201968 DE 19722201968 DE 2201968 A DE2201968 A DE 2201968A DE 2201968 A1 DE2201968 A1 DE 2201968A1
- Authority
- DE
- Germany
- Prior art keywords
- benzoxazole
- carboxylic acid
- carboxamide
- benzoxazol
- acid hydrazide
- 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.)
- Pending
Links
- 238000002360 preparation method Methods 0.000 title claims description 12
- 239000002537 cosmetic Substances 0.000 title claims description 10
- -1 aliphatic hydrocarbon radical Chemical class 0.000 claims description 42
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 13
- VKPJOERCBNIOLN-UHFFFAOYSA-N 1,3-benzoxazole-2-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)=NC2=C1 VKPJOERCBNIOLN-UHFFFAOYSA-N 0.000 claims description 11
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 11
- 206010042496 Sunburn Diseases 0.000 claims description 10
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 10
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 8
- 230000000475 sunscreen effect Effects 0.000 claims description 7
- 239000000516 sunscreening agent Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- GCXMFUAGOGIXMO-UHFFFAOYSA-N 2-(1,3-benzoxazole-2-carbothioyl)isoindole-1,3-dione Chemical compound O1C(=NC2=C1C=CC=C2)C(=S)N2C(C=1C(C2=O)=CC=CC1)=O GCXMFUAGOGIXMO-UHFFFAOYSA-N 0.000 claims description 3
- CWIWLRVMGGGOFT-UHFFFAOYSA-N 5-methyl-1,3-benzoxazole-2-carbothioamide Chemical compound CC1=CC=C2OC(C(N)=S)=NC2=C1 CWIWLRVMGGGOFT-UHFFFAOYSA-N 0.000 claims description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- RVAXPDUJRZQZLN-UHFFFAOYSA-N 1,3-benzoxazol-2-yl(pyrrolidin-1-yl)methanone Chemical compound O1C(=NC2=C1C=CC=C2)C(=O)N2CCCC2 RVAXPDUJRZQZLN-UHFFFAOYSA-N 0.000 claims description 2
- YBJRNJOJOMXGQG-UHFFFAOYSA-N CC(C=C1)=CC2=C1OC(C(N(C(C1=CC=CC=C11)=O)C1=O)=S)=N2 Chemical compound CC(C=C1)=CC2=C1OC(C(N(C(C1=CC=CC=C11)=O)C1=O)=S)=N2 YBJRNJOJOMXGQG-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000005521 carbonamide group Chemical group 0.000 claims description 2
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims description 2
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims description 2
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 150000003839 salts Chemical group 0.000 claims description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 1
- WTDDCMGCDVMHQY-UHFFFAOYSA-N COC(C=C1)=CC=C1C(N1C(C=CC=C2)=C2OC1C(NN)=O)=O Chemical compound COC(C=C1)=CC=C1C(N1C(C=CC=C2)=C2OC1C(NN)=O)=O WTDDCMGCDVMHQY-UHFFFAOYSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000002844 melting Methods 0.000 description 31
- 230000008018 melting Effects 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000000354 decomposition reaction Methods 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 238000009835 boiling Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 229920002307 Dextran Polymers 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- KYXMYOBSPMTLNF-UHFFFAOYSA-N 1,3-benzoxazole-2-carbothioamide Chemical compound C1=CC=C2OC(C(=S)N)=NC2=C1 KYXMYOBSPMTLNF-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 210000002683 foot Anatomy 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 4
- 206010030113 Oedema Diseases 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- VKHNEIIQEKUELV-UHFFFAOYSA-N 1,3-benzoxazole-2-carbohydrazide Chemical compound C1=CC=C2OC(C(=O)NN)=NC2=C1 VKHNEIIQEKUELV-UHFFFAOYSA-N 0.000 description 3
- WHHYMBKESAOOSX-UHFFFAOYSA-N 1,3-benzoxazole-2-carboxamide Chemical compound C1=CC=C2OC(C(=O)N)=NC2=C1 WHHYMBKESAOOSX-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 description 3
- 150000003857 carboxamides Chemical class 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical compound NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 2
- KRDOPTYJCJHYRI-UHFFFAOYSA-N n-propan-2-yl-1,3-benzoxazole-2-carboxamide Chemical compound C1=CC=C2OC(C(=O)NC(C)C)=NC2=C1 KRDOPTYJCJHYRI-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000011837 pasties Nutrition 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WELHBLLMEXKKEH-UHFFFAOYSA-N 1,3-benzoxazole-2-carbonitrile Chemical class C1=CC=C2OC(C#N)=NC2=C1 WELHBLLMEXKKEH-UHFFFAOYSA-N 0.000 description 1
- DGPQCLAUESWVAM-UHFFFAOYSA-N 1,3-benzoxazole-2-carbothioic s-acid Chemical class C1=CC=C2OC(C(=O)S)=NC2=C1 DGPQCLAUESWVAM-UHFFFAOYSA-N 0.000 description 1
- DEYNNQVBVKSMPV-UHFFFAOYSA-N 1,3-benzoxazole-5-carboxamide Chemical compound NC(=O)C1=CC=C2OC=NC2=C1 DEYNNQVBVKSMPV-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- FLFBJLVWUWOFTE-UHFFFAOYSA-N 3-chloro-1,4-benzoxazin-2-one Chemical class C1=CC=C2OC(=O)C(Cl)=NC2=C1 FLFBJLVWUWOFTE-UHFFFAOYSA-N 0.000 description 1
- REKQLYUAUXYJSZ-UHFFFAOYSA-N 4-methoxybenzohydrazide Chemical compound COC1=CC=C(C(=O)NN)C=C1 REKQLYUAUXYJSZ-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- IQQKXTVYGHYXFX-UHFFFAOYSA-N 5-methoxy-1,3-benzoxazole Chemical compound COC1=CC=C2OC=NC2=C1 IQQKXTVYGHYXFX-UHFFFAOYSA-N 0.000 description 1
- SNQUKJWKYRHONV-UHFFFAOYSA-N 5-methoxy-1,3-benzoxazole-2-carboxylic acid Chemical compound COC1=CC=C2OC(C(O)=O)=NC2=C1 SNQUKJWKYRHONV-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000006877 Insect Bites and Stings Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- ONAUIWQEAZPQEI-UHFFFAOYSA-N methyl 5-nitro-1,3-benzoxazole-2-carboxylate Chemical compound [O-][N+](=O)C1=CC=C2OC(C(=O)OC)=NC2=C1 ONAUIWQEAZPQEI-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 210000000453 second toe Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000037072 sun protection Effects 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 210000000431 third toe Anatomy 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Cosmetics (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE794063D BE794063A (fr) | 1972-01-17 | Anti-inflammatoires pour compositions cosmetiques | |
| DE19722201968 DE2201968A1 (de) | 1972-01-17 | 1972-01-17 | Entzuendungshemmer fuer kosmetische praeparationen |
| NL7216061A NL7216061A (enrdf_load_html_response) | 1972-01-17 | 1972-11-27 | |
| GB5904472A GB1381319A (en) | 1972-01-17 | 1972-12-21 | Inflammation preventatives for cosmetic preparations |
| GB451874A GB1381320A (en) | 1972-01-17 | 1972-12-21 | Benzoxazole derivatives |
| FR7246018A FR2168302B1 (enrdf_load_html_response) | 1972-01-17 | 1972-12-22 | |
| BR009121/72A BR7209121D0 (pt) | 1972-01-17 | 1972-12-26 | Composicao inibidora de inflamacoes para preparacoes cosmeticas |
| JP48006681A JPS504250A (enrdf_load_html_response) | 1972-01-17 | 1973-01-16 | |
| ZA730342A ZA73342B (en) | 1972-01-17 | 1973-01-17 | Inflammation preventatives for cosmetic preparations |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722201968 DE2201968A1 (de) | 1972-01-17 | 1972-01-17 | Entzuendungshemmer fuer kosmetische praeparationen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2201968A1 true DE2201968A1 (de) | 1973-08-02 |
Family
ID=5833162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722201968 Pending DE2201968A1 (de) | 1972-01-17 | 1972-01-17 | Entzuendungshemmer fuer kosmetische praeparationen |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS504250A (enrdf_load_html_response) |
| BE (1) | BE794063A (enrdf_load_html_response) |
| BR (1) | BR7209121D0 (enrdf_load_html_response) |
| DE (1) | DE2201968A1 (enrdf_load_html_response) |
| FR (1) | FR2168302B1 (enrdf_load_html_response) |
| GB (2) | GB1381320A (enrdf_load_html_response) |
| NL (1) | NL7216061A (enrdf_load_html_response) |
| ZA (1) | ZA73342B (enrdf_load_html_response) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0012178A1 (de) * | 1978-10-31 | 1980-06-25 | Richardson-Vicks, Inc. | Benzoxazolderivate, Verfahren zu deren Herstellung, kosmetische Mittel enthaltend solche Verbindungen, Verwendung solcher Verbindungen als UV-A-Filter sowie Verfahren zum Schützen der Haut und Haare und Verfahren zum Stabilisieren kosmetischer Mittel |
| EP0127066A3 (en) * | 1983-05-20 | 1987-12-16 | Usv Pharmaceutical Corporation | Composition for treating asthma |
| US7482466B2 (en) * | 2003-04-07 | 2009-01-27 | Pharmacyclics, Inc. | Hydroxamates as therapeutic agents |
| US9128096B2 (en) | 2007-01-30 | 2015-09-08 | Pharmacyclics, Inc. | Methods for determining cancer resistance to histone deacetylase inhibitors |
| US9403032B2 (en) | 2009-04-17 | 2016-08-02 | Pharmacyclics Llc | Formulations of histone deacetylase inhibitor and uses therof |
| US9408816B2 (en) | 2006-12-26 | 2016-08-09 | Pharmacyclics Llc | Method of using histone deacetylase inhibitors and monitoring biomarkers in combination therapy |
| US9421208B2 (en) | 2013-08-02 | 2016-08-23 | Pharmacyclics Llc | Methods for the treatment of solid tumors |
| US9492423B2 (en) | 2011-09-13 | 2016-11-15 | Pharmacyclics Llc | Formulations of histone deacetylase inhibitor in combination with bendamustine and uses thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12122770B1 (en) * | 2023-10-23 | 2024-10-22 | King Faisal University | 2-(benzo[d]oxazol-2-yl)-n'-(nicotinoyloxy)acetimidamide as an antimicrobial compound |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1348752A (fr) * | 1962-02-07 | 1964-01-10 | Bayer Ag | Procédé de préparation de benzoxazine-(1, 4)-ones-(2) 3-substituées et de dérivés d'acide benzoxazol-2-carboxylique |
-
0
- BE BE794063D patent/BE794063A/xx unknown
-
1972
- 1972-01-17 DE DE19722201968 patent/DE2201968A1/de active Pending
- 1972-11-27 NL NL7216061A patent/NL7216061A/xx unknown
- 1972-12-21 GB GB451874A patent/GB1381320A/en not_active Expired
- 1972-12-21 GB GB5904472A patent/GB1381319A/en not_active Expired
- 1972-12-22 FR FR7246018A patent/FR2168302B1/fr not_active Expired
- 1972-12-26 BR BR009121/72A patent/BR7209121D0/pt unknown
-
1973
- 1973-01-16 JP JP48006681A patent/JPS504250A/ja active Pending
- 1973-01-17 ZA ZA730342A patent/ZA73342B/xx unknown
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0012178A1 (de) * | 1978-10-31 | 1980-06-25 | Richardson-Vicks, Inc. | Benzoxazolderivate, Verfahren zu deren Herstellung, kosmetische Mittel enthaltend solche Verbindungen, Verwendung solcher Verbindungen als UV-A-Filter sowie Verfahren zum Schützen der Haut und Haare und Verfahren zum Stabilisieren kosmetischer Mittel |
| EP0127066A3 (en) * | 1983-05-20 | 1987-12-16 | Usv Pharmaceutical Corporation | Composition for treating asthma |
| US8779171B2 (en) | 2003-04-07 | 2014-07-15 | Pharmacyclics, Inc. | Hydroxamates as therapeutic agents |
| US7834054B2 (en) | 2003-04-07 | 2010-11-16 | Pharmacyclics, Inc. | Hydroxamates as therapeutic agents |
| US8026371B2 (en) | 2003-04-07 | 2011-09-27 | Pharmacyclics, Inc. | Hydroxamates as therapeutic agents |
| US8389570B2 (en) | 2003-04-07 | 2013-03-05 | Pharmacyclics, Inc. | Hydroxamates as therapeutic agents |
| US7482466B2 (en) * | 2003-04-07 | 2009-01-27 | Pharmacyclics, Inc. | Hydroxamates as therapeutic agents |
| US9186347B1 (en) | 2003-04-07 | 2015-11-17 | Pharmacyclics Llc | Hydroxamates as therapeutic agents |
| US9408816B2 (en) | 2006-12-26 | 2016-08-09 | Pharmacyclics Llc | Method of using histone deacetylase inhibitors and monitoring biomarkers in combination therapy |
| US9128096B2 (en) | 2007-01-30 | 2015-09-08 | Pharmacyclics, Inc. | Methods for determining cancer resistance to histone deacetylase inhibitors |
| US9403032B2 (en) | 2009-04-17 | 2016-08-02 | Pharmacyclics Llc | Formulations of histone deacetylase inhibitor and uses therof |
| US9492423B2 (en) | 2011-09-13 | 2016-11-15 | Pharmacyclics Llc | Formulations of histone deacetylase inhibitor in combination with bendamustine and uses thereof |
| US9421208B2 (en) | 2013-08-02 | 2016-08-23 | Pharmacyclics Llc | Methods for the treatment of solid tumors |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS504250A (enrdf_load_html_response) | 1975-01-17 |
| GB1381319A (en) | 1975-01-22 |
| BR7209121D0 (pt) | 1973-12-11 |
| FR2168302B1 (enrdf_load_html_response) | 1975-11-28 |
| GB1381320A (en) | 1975-01-22 |
| BE794063A (fr) | 1973-07-16 |
| ZA73342B (en) | 1973-10-31 |
| NL7216061A (enrdf_load_html_response) | 1973-07-19 |
| FR2168302A1 (enrdf_load_html_response) | 1973-08-31 |
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