NO325684B1 - Gelformulering for topisk legemiddellevering - Google Patents
Gelformulering for topisk legemiddellevering Download PDFInfo
- Publication number
- NO325684B1 NO325684B1 NO19992638A NO992638A NO325684B1 NO 325684 B1 NO325684 B1 NO 325684B1 NO 19992638 A NO19992638 A NO 19992638A NO 992638 A NO992638 A NO 992638A NO 325684 B1 NO325684 B1 NO 325684B1
- Authority
- NO
- Norway
- Prior art keywords
- formulation
- imidazo
- ethoxymethyl
- quinoline
- dimethyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 87
- 238000009472 formulation Methods 0.000 title claims abstract description 81
- 230000000699 topical effect Effects 0.000 title abstract description 11
- 238000012377 drug delivery Methods 0.000 title abstract 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 72
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 claims abstract description 53
- BXNMTOQRYBFHNZ-UHFFFAOYSA-N resiquimod Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CC(C)(C)O)C3=C(N)N=C21 BXNMTOQRYBFHNZ-UHFFFAOYSA-N 0.000 claims abstract description 41
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 31
- 229940075614 colloidal silicon dioxide Drugs 0.000 claims abstract description 27
- 235000013773 glyceryl triacetate Nutrition 0.000 claims abstract description 26
- 239000001087 glyceryl triacetate Substances 0.000 claims abstract description 26
- 229960002622 triacetin Drugs 0.000 claims abstract description 26
- 235000013772 propylene glycol Nutrition 0.000 claims abstract description 24
- 238000011200 topical administration Methods 0.000 claims 1
- 239000000499 gel Substances 0.000 abstract description 44
- 229940079593 drug Drugs 0.000 abstract description 27
- 239000003814 drug Substances 0.000 abstract description 27
- 102000014150 Interferons Human genes 0.000 abstract description 15
- 108010050904 Interferons Proteins 0.000 abstract description 15
- 229940079322 interferon Drugs 0.000 abstract description 13
- 108060008682 Tumor Necrosis Factor Proteins 0.000 abstract description 12
- 102000003390 tumor necrosis factor Human genes 0.000 abstract description 12
- 102000004127 Cytokines Human genes 0.000 abstract description 11
- 108090000695 Cytokines Proteins 0.000 abstract description 11
- 201000010099 disease Diseases 0.000 abstract description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 7
- 238000012384 transportation and delivery Methods 0.000 abstract description 6
- 239000008252 pharmaceutical gel Substances 0.000 abstract description 5
- 210000004400 mucous membrane Anatomy 0.000 abstract description 4
- 241000124008 Mammalia Species 0.000 abstract description 3
- 230000009854 mucosal lesion Effects 0.000 abstract description 3
- 210000004027 cell Anatomy 0.000 description 20
- 239000012530 fluid Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 238000010998 test method Methods 0.000 description 11
- 210000004379 membrane Anatomy 0.000 description 10
- 239000012528 membrane Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 238000009792 diffusion process Methods 0.000 description 9
- 230000006698 induction Effects 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 8
- 230000000694 effects Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 208000009889 Herpes Simplex Diseases 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 206010059313 Anogenital warts Diseases 0.000 description 3
- 208000000907 Condylomata Acuminata Diseases 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 208000025009 anogenital human papillomavirus infection Diseases 0.000 description 3
- 201000004201 anogenital venereal wart Diseases 0.000 description 3
- 238000004166 bioassay Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012385 systemic delivery Methods 0.000 description 3
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 206010019233 Headaches Diseases 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 206010037660 Pyrexia Diseases 0.000 description 2
- 208000036142 Viral infection Diseases 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 206010047700 Vomiting Diseases 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- 230000036760 body temperature Effects 0.000 description 2
- 210000005056 cell body Anatomy 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 230000000120 cytopathologic effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 231100000869 headache Toxicity 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229940047124 interferons Drugs 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 206010025482 malaise Diseases 0.000 description 2
- 229940068196 placebo Drugs 0.000 description 2
- 239000000902 placebo Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007974 sodium acetate buffer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 229940042129 topical gel Drugs 0.000 description 2
- 239000012049 topical pharmaceutical composition Substances 0.000 description 2
- 230000009385 viral infection Effects 0.000 description 2
- 230000003612 virological effect Effects 0.000 description 2
- LOGFVTREOLYCPF-KXNHARMFSA-N (2s,3r)-2-[[(2r)-1-[(2s)-2,6-diaminohexanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxybutanoic acid Chemical compound C[C@@H](O)[C@@H](C(O)=O)NC(=O)[C@H]1CCCN1C(=O)[C@@H](N)CCCCN LOGFVTREOLYCPF-KXNHARMFSA-N 0.000 description 1
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 206010004146 Basal cell carcinoma Diseases 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 206010008263 Cervical dysplasia Diseases 0.000 description 1
- 238000008157 ELISA kit Methods 0.000 description 1
- 102000006992 Interferon-alpha Human genes 0.000 description 1
- 108010047761 Interferon-alpha Proteins 0.000 description 1
- 102000003777 Interleukin-1 beta Human genes 0.000 description 1
- 108090000193 Interleukin-1 beta Proteins 0.000 description 1
- 102000004125 Interleukin-1alpha Human genes 0.000 description 1
- 108010082786 Interleukin-1alpha Proteins 0.000 description 1
- 102000004889 Interleukin-6 Human genes 0.000 description 1
- 108090001005 Interleukin-6 Proteins 0.000 description 1
- 102000004890 Interleukin-8 Human genes 0.000 description 1
- 108090001007 Interleukin-8 Proteins 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000012979 RPMI medium Substances 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000700584 Simplexvirus Species 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 208000000260 Warts Diseases 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 208000009621 actinic keratosis Diseases 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 208000007951 cervical intraepithelial neoplasia Diseases 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 229940100601 interleukin-6 Drugs 0.000 description 1
- 229940096397 interleukin-8 Drugs 0.000 description 1
- XKTZWUACRZHVAN-VADRZIEHSA-N interleukin-8 Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](NC(C)=O)CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N1[C@H](CCC1)C(=O)N1[C@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC(O)=CC=1)C(=O)N[C@H](CO)C(=O)N1[C@H](CCC1)C(N)=O)C1=CC=CC=C1 XKTZWUACRZHVAN-VADRZIEHSA-N 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- PQLXHQMOHUQAKB-UHFFFAOYSA-N miltefosine Chemical compound CCCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C PQLXHQMOHUQAKB-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 1
- 239000008250 pharmaceutical cream Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- -1 polyethylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- OJTDGPLHRSZIAV-UHFFFAOYSA-N propane-1,2-diol Chemical compound CC(O)CO.CC(O)CO OJTDGPLHRSZIAV-UHFFFAOYSA-N 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 201000010153 skin papilloma Diseases 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000002943 spectrophotometric absorbance Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- 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
- A61K47/02—Inorganic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- 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
- 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
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dermatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Virology (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Inorganic Chemistry (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/759,992 US5939090A (en) | 1996-12-03 | 1996-12-03 | Gel formulations for topical drug delivery |
| PCT/US1997/021995 WO1998024436A2 (en) | 1996-12-03 | 1997-12-01 | Gel formulations for topical drug delivery |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO992638D0 NO992638D0 (no) | 1999-06-01 |
| NO992638L NO992638L (no) | 1999-07-16 |
| NO325684B1 true NO325684B1 (no) | 2008-07-07 |
Family
ID=25057713
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19992638A NO325684B1 (no) | 1996-12-03 | 1999-06-01 | Gelformulering for topisk legemiddellevering |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US5939090A (ko) |
| EP (1) | EP0942724B1 (ko) |
| JP (1) | JP4615633B2 (ko) |
| KR (1) | KR100503716B1 (ko) |
| AT (1) | ATE245422T1 (ko) |
| AU (1) | AU723897B2 (ko) |
| BR (1) | BR9713677B1 (ko) |
| CA (1) | CA2273094C (ko) |
| CZ (1) | CZ301713B6 (ko) |
| DE (1) | DE69723721T2 (ko) |
| DK (1) | DK0942724T3 (ko) |
| ES (1) | ES2200206T3 (ko) |
| HU (1) | HU229599B1 (ko) |
| IL (1) | IL130065A (ko) |
| NO (1) | NO325684B1 (ko) |
| NZ (1) | NZ335821A (ko) |
| PT (1) | PT942724E (ko) |
| WO (1) | WO1998024436A2 (ko) |
Families Citing this family (162)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5741908A (en) | 1996-06-21 | 1998-04-21 | Minnesota Mining And Manufacturing Company | Process for reparing imidazoquinolinamines |
| UA67760C2 (uk) | 1997-12-11 | 2004-07-15 | Міннесота Майнінг Енд Мануфакчурінг Компані | Імідазонафтиридин та тетрагідроімідазонафтиридин, фармацевтична композиція, спосіб індукування біосинтезу цитокінів та спосіб лікування вірусної інфекції, проміжні сполуки |
| US6518280B2 (en) | 1998-12-11 | 2003-02-11 | 3M Innovative Properties Company | Imidazonaphthyridines |
| US6486168B1 (en) | 1999-01-08 | 2002-11-26 | 3M Innovative Properties Company | Formulations and methods for treatment of mucosal associated conditions with an immune response modifier |
| JP2002534377A (ja) * | 1999-01-08 | 2002-10-15 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫応答調節因子を用いて粘膜関連の病態を治療するための製剤および方法 |
| EP1495758A3 (en) * | 1999-01-08 | 2005-04-13 | 3M Innovative Properties Company | Formulations and methods for treatment of mucosal associated conditions with an immune response modifier |
| US20020058674A1 (en) | 1999-01-08 | 2002-05-16 | Hedenstrom John C. | Systems and methods for treating a mucosal surface |
| US6558951B1 (en) * | 1999-02-11 | 2003-05-06 | 3M Innovative Properties Company | Maturation of dendritic cells with immune response modifying compounds |
| US6331539B1 (en) * | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| US6573273B1 (en) | 1999-06-10 | 2003-06-03 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6541485B1 (en) | 1999-06-10 | 2003-04-01 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6756382B2 (en) * | 1999-06-10 | 2004-06-29 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6916925B1 (en) | 1999-11-05 | 2005-07-12 | 3M Innovative Properties Co. | Dye labeled imidazoquinoline compounds |
| US6376669B1 (en) | 1999-11-05 | 2002-04-23 | 3M Innovative Properties Company | Dye labeled imidazoquinoline compounds |
| JP3436512B2 (ja) * | 1999-12-28 | 2003-08-11 | 株式会社デンソー | アクセル装置 |
| US6787342B2 (en) * | 2000-02-16 | 2004-09-07 | Merial Limited | Paste formulations |
| US6894060B2 (en) * | 2000-03-30 | 2005-05-17 | 3M Innovative Properties Company | Method for the treatment of dermal lesions caused by envenomation |
| PL361975A1 (en) * | 2000-06-22 | 2004-10-18 | 3M Innovative Properties Company | Systems and methods for treating a mucosal surface |
| DE10033853A1 (de) * | 2000-07-12 | 2002-01-31 | Hexal Ag | Transdermales therapeutisches System mit hochdispersem Siliziumdioxid |
| AU2001281304B2 (en) | 2000-08-15 | 2006-05-25 | Surmodics, Inc. | Medicament incorporation matrix |
| US20020055517A1 (en) * | 2000-09-15 | 2002-05-09 | 3M Innovative Properties Company | Methods for delaying recurrence of herpes virus symptoms |
| JP2002145777A (ja) * | 2000-11-06 | 2002-05-22 | Sumitomo Pharmaceut Co Ltd | アラキドン酸誘発皮膚疾患治療剤 |
| US6525064B1 (en) | 2000-12-08 | 2003-02-25 | 3M Innovative Properties Company | Sulfonamido substituted imidazopyridines |
| US6664260B2 (en) | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Heterocyclic ether substituted imidazoquinolines |
| US6664264B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| US6545017B1 (en) * | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Urea substituted imidazopyridines |
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| IL92537A (en) * | 1988-12-15 | 1994-04-12 | Riker Laboratories Inc | Topical preparations and dermal systems containing 1-isobutyl-H1-imidazo [C-4,5] quinoline-4-amine |
| DE69029212T2 (de) * | 1989-02-27 | 1997-05-22 | Riker Laboratories Inc | 4-Amino-1H-Imidazo(4,5-c)chinoline als antivirale Mittel |
| DK0872478T3 (da) * | 1991-03-01 | 2003-03-31 | Minnesota Mining & Mfg | Mellemprodukter til fremstilling af 1-substituerede, 2-substituerede 1H-imidazo[4,5-c]quinolin-4-aminer |
| US5389640A (en) * | 1991-03-01 | 1995-02-14 | Minnesota Mining And Manufacturing Company | 1-substituted, 2-substituted 1H-imidazo[4,5-c]quinolin-4-amines |
| DE4117249C2 (de) * | 1991-05-27 | 1998-05-14 | Christian Dr Stief | Linsidomin zur Behandlung erektiler Dysfunktionen |
-
1996
- 1996-12-03 US US08/759,992 patent/US5939090A/en not_active Expired - Lifetime
-
1997
- 1997-12-01 AT AT97950772T patent/ATE245422T1/de active
- 1997-12-01 CZ CZ0195599A patent/CZ301713B6/cs not_active IP Right Cessation
- 1997-12-01 JP JP52574098A patent/JP4615633B2/ja not_active Expired - Fee Related
- 1997-12-01 WO PCT/US1997/021995 patent/WO1998024436A2/en active IP Right Grant
- 1997-12-01 NZ NZ335821A patent/NZ335821A/en not_active IP Right Cessation
- 1997-12-01 DK DK97950772T patent/DK0942724T3/da active
- 1997-12-01 EP EP97950772A patent/EP0942724B1/en not_active Expired - Lifetime
- 1997-12-01 KR KR10-1999-7004821A patent/KR100503716B1/ko not_active IP Right Cessation
- 1997-12-01 PT PT97950772T patent/PT942724E/pt unknown
- 1997-12-01 IL IL13006597A patent/IL130065A/en not_active IP Right Cessation
- 1997-12-01 ES ES97950772T patent/ES2200206T3/es not_active Expired - Lifetime
- 1997-12-01 CA CA002273094A patent/CA2273094C/en not_active Expired - Fee Related
- 1997-12-01 HU HU0000568A patent/HU229599B1/hu not_active IP Right Cessation
- 1997-12-01 BR BRPI9713677-8A patent/BR9713677B1/pt not_active IP Right Cessation
- 1997-12-01 AU AU53686/98A patent/AU723897B2/en not_active Ceased
- 1997-12-01 DE DE69723721T patent/DE69723721T2/de not_active Expired - Lifetime
-
1999
- 1999-06-01 NO NO19992638A patent/NO325684B1/no not_active IP Right Cessation
- 1999-06-04 US US09/325,369 patent/US6365166B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US5939090A (en) | 1999-08-17 |
| WO1998024436A2 (en) | 1998-06-11 |
| US20020015715A1 (en) | 2002-02-07 |
| KR20000069233A (ko) | 2000-11-25 |
| BR9713677B1 (pt) | 2009-05-05 |
| IL130065A0 (en) | 2000-02-29 |
| EP0942724B1 (en) | 2003-07-23 |
| DK0942724T3 (da) | 2003-11-17 |
| PT942724E (pt) | 2003-12-31 |
| NZ335821A (en) | 2001-04-27 |
| IL130065A (en) | 2004-06-20 |
| CZ301713B6 (cs) | 2010-06-02 |
| HU229599B1 (hu) | 2014-02-28 |
| JP2001501968A (ja) | 2001-02-13 |
| NO992638D0 (no) | 1999-06-01 |
| CA2273094C (en) | 2005-08-16 |
| EP0942724A2 (en) | 1999-09-22 |
| ATE245422T1 (de) | 2003-08-15 |
| DE69723721T2 (de) | 2004-04-15 |
| BR9713677A (pt) | 2000-03-28 |
| AU5368698A (en) | 1998-06-29 |
| NO992638L (no) | 1999-07-16 |
| JP4615633B2 (ja) | 2011-01-19 |
| HUP0000568A3 (en) | 2001-01-29 |
| ES2200206T3 (es) | 2004-03-01 |
| HUP0000568A2 (hu) | 2000-10-28 |
| KR100503716B1 (ko) | 2005-07-26 |
| WO1998024436A3 (en) | 1998-08-06 |
| DE69723721D1 (de) | 2003-08-28 |
| AU723897B2 (en) | 2000-09-07 |
| CZ195599A3 (cs) | 1999-09-15 |
| CA2273094A1 (en) | 1998-06-11 |
| US6365166B2 (en) | 2002-04-02 |
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| Date | Code | Title | Description |
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| MM1K | Lapsed by not paying the annual fees |