IL95528A - Topical antiinflammatory compositions with minimal systemic absorption containing indole or naphtol derivatives - Google Patents
Topical antiinflammatory compositions with minimal systemic absorption containing indole or naphtol derivativesInfo
- Publication number
- IL95528A IL95528A IL9552890A IL9552890A IL95528A IL 95528 A IL95528 A IL 95528A IL 9552890 A IL9552890 A IL 9552890A IL 9552890 A IL9552890 A IL 9552890A IL 95528 A IL95528 A IL 95528A
- Authority
- IL
- Israel
- Prior art keywords
- composition
- polyethylene glycol
- base
- compound
- naphthol
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 80
- 230000003110 anti-inflammatory effect Effects 0.000 title claims abstract description 19
- 238000010521 absorption reaction Methods 0.000 title claims description 21
- 230000009885 systemic effect Effects 0.000 title claims description 12
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title claims description 9
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title claims description 7
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title claims description 7
- 230000000699 topical effect Effects 0.000 title abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 46
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 41
- 239000012049 topical pharmaceutical composition Substances 0.000 claims abstract description 19
- CZTSOXCSVFEFIK-UHFFFAOYSA-N 2-benzylnaphthalen-1-ol Chemical compound C1=CC2=CC=CC=C2C(O)=C1CC1=CC=CC=C1 CZTSOXCSVFEFIK-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
- 201000004624 Dermatitis Diseases 0.000 claims description 12
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 12
- 229940068918 polyethylene glycol 400 Drugs 0.000 claims description 9
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- ONONEWXVNTXZIT-UHFFFAOYSA-N 2-(5-methylhexyl)naphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(CCCCC(C)C)=CC=C21 ONONEWXVNTXZIT-UHFFFAOYSA-N 0.000 claims description 2
- SXGZZKOBTKWQQC-UHFFFAOYSA-N 2-(furan-2-ylmethyl)naphthalen-1-ol Chemical compound C1=CC2=CC=CC=C2C(O)=C1CC1=CC=CO1 SXGZZKOBTKWQQC-UHFFFAOYSA-N 0.000 claims description 2
- KWGHSFDXFQUJHX-UHFFFAOYSA-N 2-[(3-chlorophenyl)methyl]naphthalen-1-ol Chemical compound C1=CC2=CC=CC=C2C(O)=C1CC1=CC=CC(Cl)=C1 KWGHSFDXFQUJHX-UHFFFAOYSA-N 0.000 claims description 2
- QTOSHGHQFMHMIN-UHFFFAOYSA-N 2-[(3-fluorophenyl)methyl]naphthalen-1-ol Chemical compound C1=CC2=CC=CC=C2C(O)=C1CC1=CC=CC(F)=C1 QTOSHGHQFMHMIN-UHFFFAOYSA-N 0.000 claims description 2
- SUMZRFZVYOPDSE-UHFFFAOYSA-N 2-[(4-bromophenyl)methyl]naphthalen-1-ol Chemical compound C1=CC2=CC=CC=C2C(O)=C1CC1=CC=C(Br)C=C1 SUMZRFZVYOPDSE-UHFFFAOYSA-N 0.000 claims description 2
- YYFKPFDHALEREI-UHFFFAOYSA-N 2-[(4-ethoxyphenyl)methyl]naphthalen-1-ol Chemical compound C1=CC(OCC)=CC=C1CC1=CC=C(C=CC=C2)C2=C1O YYFKPFDHALEREI-UHFFFAOYSA-N 0.000 claims description 2
- ZHOKFMVXIRHAMR-UHFFFAOYSA-N 2-prop-2-enylnaphthalen-1-ol Chemical compound C1=CC=C2C(O)=C(CC=C)C=CC2=C1 ZHOKFMVXIRHAMR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- GKOQVDAGVTZSIE-UHFFFAOYSA-N ethyl 3-(1-hydroxynaphthalen-2-yl)prop-2-enoate Chemical compound C1=CC=CC2=C(O)C(C=CC(=O)OCC)=CC=C21 GKOQVDAGVTZSIE-UHFFFAOYSA-N 0.000 claims description 2
- AQZBITOADVVNBT-UHFFFAOYSA-N ethyl 3-(1-hydroxynaphthalen-2-yl)propanoate Chemical compound C1=CC=CC2=C(O)C(CCC(=O)OCC)=CC=C21 AQZBITOADVVNBT-UHFFFAOYSA-N 0.000 claims description 2
- QMGFOJFQKMUHRF-UHFFFAOYSA-N ethyl 5-(1-hydroxynaphthalen-2-yl)pent-4-enoate Chemical compound C1=CC=CC2=C(O)C(C=CCCC(=O)OCC)=CC=C21 QMGFOJFQKMUHRF-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- BQQWXPQFVOAOIO-UHFFFAOYSA-N methyl 7-(1-hydroxynaphthalen-2-yl)hept-5-ynoate Chemical compound C1=CC=CC2=C(O)C(CC#CCCCC(=O)OC)=CC=C21 BQQWXPQFVOAOIO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 24
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 12
- 229940050929 polyethylene glycol 3350 Drugs 0.000 claims 7
- 241000124008 Mammalia Species 0.000 claims 2
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 230000035515 penetration Effects 0.000 abstract description 40
- 238000009472 formulation Methods 0.000 abstract description 26
- 239000003814 drug Substances 0.000 abstract description 12
- 229940079593 drug Drugs 0.000 abstract description 12
- 230000000694 effects Effects 0.000 abstract description 11
- 238000001727 in vivo Methods 0.000 abstract description 8
- 238000000338 in vitro Methods 0.000 abstract description 6
- 150000002475 indoles Chemical class 0.000 abstract description 4
- -1 2-substituted-1-naphthols Chemical class 0.000 abstract description 2
- 231100000057 systemic toxicity Toxicity 0.000 abstract description 2
- 210000003491 skin Anatomy 0.000 description 68
- 239000002674 ointment Substances 0.000 description 35
- 239000006071 cream Substances 0.000 description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 27
- 239000003981 vehicle Substances 0.000 description 23
- 241000700159 Rattus Species 0.000 description 18
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 17
- 210000002700 urine Anatomy 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 210000003608 fece Anatomy 0.000 description 12
- 239000004264 Petrolatum Substances 0.000 description 10
- 229940066842 petrolatum Drugs 0.000 description 10
- 235000019271 petrolatum Nutrition 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 230000004907 flux Effects 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 8
- 229920002562 Polyethylene Glycol 3350 Polymers 0.000 description 7
- PHEDXBVPIONUQT-RGYGYFBISA-N phorbol 13-acetate 12-myristate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCCCCCC)C(CO)=C[C@H]1[C@H]1[C@]2(OC(C)=O)C1(C)C PHEDXBVPIONUQT-RGYGYFBISA-N 0.000 description 7
- 210000000434 stratum corneum Anatomy 0.000 description 7
- 230000008961 swelling Effects 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 210000004207 dermis Anatomy 0.000 description 6
- 238000009792 diffusion process Methods 0.000 description 6
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 6
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 5
- 206010030113 Oedema Diseases 0.000 description 5
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 5
- 206010061218 Inflammation Diseases 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 210000005069 ears Anatomy 0.000 description 4
- 210000002615 epidermis Anatomy 0.000 description 4
- 230000029142 excretion Effects 0.000 description 4
- 230000004054 inflammatory process Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 201000004681 Psoriasis Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 description 3
- 239000002260 anti-inflammatory agent Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000001684 chronic effect Effects 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 3
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 3
- 229960002216 methylparaben Drugs 0.000 description 3
- 230000035699 permeability Effects 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 3
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 3
- 229960003415 propylparaben Drugs 0.000 description 3
- 230000001839 systemic circulation Effects 0.000 description 3
- VIKLWVOGWXUWEY-UHFFFAOYSA-N (5-benzyl-1-methylindol-4-yl) acetate Chemical compound C1=CC=2N(C)C=CC=2C(OC(=O)C)=C1CC1=CC=CC=C1 VIKLWVOGWXUWEY-UHFFFAOYSA-N 0.000 description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 102000003820 Lipoxygenases Human genes 0.000 description 2
- 108090000128 Lipoxygenases Proteins 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 230000037311 normal skin Effects 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 208000017520 skin disease Diseases 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 108010088751 Albumins Proteins 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 239000005331 crown glasses (windows) Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- BJYQCDMXMKBCEV-UHFFFAOYSA-N ethyl 5-(1-hydroxynaphthalen-2-yl)pentanoate Chemical compound C1=CC=CC2=C(O)C(CCCCC(=O)OCC)=CC=C21 BJYQCDMXMKBCEV-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002550 fecal effect Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 238000007390 skin biopsy Methods 0.000 description 1
- 231100000245 skin permeability Toxicity 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000003860 topical agent Substances 0.000 description 1
- 239000006208 topical dosage form Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/14—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with at least one hydroxy group on a condensed ring system containing two rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/13—Burn treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dermatology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/400,404 US5091379A (en) | 1989-08-31 | 1989-08-31 | Topical antinflammatory compositions with minimal systemic absorption |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL95528A true IL95528A (en) | 1994-07-31 |
Family
ID=23583474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9552890A IL95528A (en) | 1989-08-31 | 1990-08-30 | Topical antiinflammatory compositions with minimal systemic absorption containing indole or naphtol derivatives |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5091379A (ja) |
| EP (1) | EP0493404A4 (ja) |
| JP (1) | JPH05501871A (ja) |
| AU (1) | AU636547B2 (ja) |
| CA (1) | CA2064189A1 (ja) |
| IE (1) | IE903163A1 (ja) |
| IL (1) | IL95528A (ja) |
| NZ (1) | NZ235081A (ja) |
| WO (1) | WO1991003227A1 (ja) |
| ZA (1) | ZA906970B (ja) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6086905A (en) * | 1991-03-21 | 2000-07-11 | Peck; James V. | Topical compositions useful as skin penetration barriers |
| US5505948A (en) * | 1993-06-01 | 1996-04-09 | Dermatology Home Products, Inc. | Home skin peel composition for producing healthy and attractive skin |
| WO1997003057A1 (en) * | 1995-07-07 | 1997-01-30 | Durham Pharmaceuticals, Llc | Cyclic amides and derivatives thereof |
| DE19746250A1 (de) * | 1997-10-20 | 1999-04-22 | Henkel Kgaa | Verwendung von substitutierten alpha-Naphtolen zum Färben von Keratinfasern |
| US20020006913A1 (en) | 1997-11-04 | 2002-01-17 | Von Borstel Reid W. | Antimutagenic compositions for treatment and prevention of photodamage to skin |
| US6203796B1 (en) | 1999-07-08 | 2001-03-20 | Andreas D. Papaprodromou | Oregano-based therapeutic composition |
| US6835184B1 (en) * | 1999-09-24 | 2004-12-28 | Becton, Dickinson And Company | Method and device for abrading skin |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL105672C (ja) * | ||||
| US4473565A (en) * | 1976-05-13 | 1984-09-25 | Johnson & Johnson | Topical anti-inflammatory drug therapy |
| CA1196284A (en) * | 1982-05-28 | 1985-11-05 | Joshua Oduro-Yeboah | Pharmaceutical formulations |
| CA1236029A (en) * | 1984-05-14 | 1988-05-03 | Edmund Sandborn | Pharmaceutical solutions comprising dimethyl sulfoxide |
| US4895727A (en) * | 1985-05-03 | 1990-01-23 | Chemex Pharmaceuticals, Inc. | Pharmaceutical vehicles for exhancing penetration and retention in the skin |
| US4833164A (en) * | 1985-05-08 | 1989-05-23 | E. I. Du Pont De Nemours And Company | 2-substituted-1-naphthols, pharmaceutical compositions of, and their use as 5-lipoxygenase inhibitors |
| GB8621008D0 (en) * | 1986-08-30 | 1986-10-08 | Smith & Nephew Ass | Pharmaceutical composition |
| US5093351A (en) * | 1989-01-05 | 1992-03-03 | Du Pont Merck Pharmaceutical Company | Substituted indole, benzofuran and benzothiophene derivatives as 5-lipoxygenase inhibitors |
-
1989
- 1989-08-31 US US07/400,404 patent/US5091379A/en not_active Expired - Fee Related
-
1990
- 1990-08-20 CA CA002064189A patent/CA2064189A1/en not_active Abandoned
- 1990-08-20 EP EP19900912810 patent/EP0493404A4/en not_active Withdrawn
- 1990-08-20 JP JP2512251A patent/JPH05501871A/ja active Pending
- 1990-08-20 AU AU62899/90A patent/AU636547B2/en not_active Ceased
- 1990-08-20 WO PCT/US1990/004598 patent/WO1991003227A1/en not_active Ceased
- 1990-08-29 NZ NZ235081A patent/NZ235081A/xx unknown
- 1990-08-30 IL IL9552890A patent/IL95528A/en not_active IP Right Cessation
- 1990-08-31 IE IE316390A patent/IE903163A1/en unknown
- 1990-08-31 ZA ZA906970A patent/ZA906970B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA906970B (en) | 1992-05-27 |
| NZ235081A (en) | 1992-10-28 |
| WO1991003227A1 (en) | 1991-03-21 |
| US5091379A (en) | 1992-02-25 |
| CA2064189A1 (en) | 1991-03-01 |
| EP0493404A4 (en) | 1992-08-12 |
| JPH05501871A (ja) | 1993-04-08 |
| AU6289990A (en) | 1991-04-08 |
| IE903163A1 (en) | 1991-03-13 |
| EP0493404A1 (en) | 1992-07-08 |
| AU636547B2 (en) | 1993-04-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RH | Patent void |