AU2001251146A1 - Method for the treatment of dermal lesions caused by envenomation - Google Patents
Method for the treatment of dermal lesions caused by envenomationInfo
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- AU2001251146A1 AU2001251146A1 AU2001251146A AU2001251146A AU2001251146A1 AU 2001251146 A1 AU2001251146 A1 AU 2001251146A1 AU 2001251146 A AU2001251146 A AU 2001251146A AU 2001251146 A AU2001251146 A AU 2001251146A AU 2001251146 A1 AU2001251146 A1 AU 2001251146A1
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Description
Method for the Treatment of Dermal Lesions Caused by Envenomation
Field of the Invention The present invention relates to methods for treating dermal lesions caused by envenomation. In particular the present invention relates to a method of treating dermal lesions caused by envenomation comprising applying a therapeutically effective amount of an immune response modifier compound selected from the group consisting of imidazoquinoline amines, imidazopyridine amines, 6,7-fused cycloalkylimidazopyridine amines, imidazonaphthyridine amines, tetrahydroimidazonaphthyridine amines, oxazolopyridine amines, oxazoloquinoline amines, thiazolopyridine amines, thiazoloquinoline amines and 1,2-bridged imidazoquinoline amines to the site of the lesion., The present invention also provides a method of preventing dermonecrosis caused by envenomation comprising applying a therapeutically effective amount of an immune response modifier compound selected from the group consisting of imidazoquinoline amines, imidazopyridine amines, 6,7-fused cycloalkylimidazopyridine amines, imidazonaphthyridine amines, tetrahydroimidazonaphthyridine amines, oxazolopyridine amines, oxazoloquinoline amines, thiazolopyridine amines, thiazoloquinoline amines and 1 ,2-bridged imidazoquinoline amines to the site of the envenomation.
Background of the Invention
Many imidazoquinoline amine, imidazopyridine amine, 6,7-fused cycloalkylimidazopyridine amine, imidazonaphthyridine amine, tetrahydroimidazonaphthyridine amine, oxazolopyridine amine, oxazoloquinoline amine, thiazolopyridine amine, thiazoloquinoline amine and 1,2-bridged imidazoquinoline amine immune response modifiers are known. These compounds are hereinafter sometimes referred to as immune response modifying compounds (IRMs). Such compounds, methods for preparing them, formulations containing them and methods of using them are disclosed in, for example, U.S. Patent Nos. 4,689,338; 5,389,640; 5,268,376; 4,929,624; 5,266,575; 5,352,784; 5,494,916; 5,482,936; 5,395,937; 5,238,944; 5,175,296; 5,693,811; 5,741,908; 5,756,747; 5,939,090; 6,110,929; 4,988,815; 5,376,076; 6,083,505; 6,039,969;
and PCT Publications WO 99/29693. WO 00/40228, WO 00/76505, WO 00/76518 and WO 00/76518.
The E M compounds have demonstrated antiviral and antitumor activity. The antiviral and antitumor activity is not direct but is believed to result from their ability to stimulate an innate immune response. In cultures of human peripheral blood mononuclear cells, members of this class of compounds have been shown to stimulate the production and release of a variety of cytokines and chemokines including interferon-α, tumor necrosis factor-α, interleukin-1 (IL-1), IL-1 receptor antagonist, IL-6, IL-8, IL-12, monocyte chemotactic protein-1 (MCP-1) and macrophage inflammatory protein (MIP- lα).
In addition to stimulating an innate immune response, the IRM compounds have been found to mediate the acquired immune response. In human peripheral blood mononuclear cell cultures, members of this class of compounds have been shown to induce the production of the T helper type 1 (THl) cytokine interferon-γ and to inhibit the production of T helper type 2 (IT 12) cytokines IL-4 and IL-5.
One of these IRM compounds, known as imiquimod (l-(2-methylpropyl)-lH- imidazo[4,5-c]quinolin-4-amine), has been commercialized in a topical formulation, Aldara™ cream, for the treatment of anogenital warts associated with human papillomavirus. Imiquimod is also being evaluated in clinical trials for use in treating superficial basal cell carcinoma and actinic kcralosis.
Another of these IRM compounds, known as resiquimod (4-amino-2- ethoxymethyl-α,α-dimethyl-lH-imidazo[4,5-c]quinoline-l-ethanol), is being evaluated in clinical trials for use in preventing genital heipes recurrences.
There are numerous venomous flora and fauna in the world, some of which possess venom that causes significant medical problems when a human or an animal is exposed to the venom. Envenomation by such a plant or animal can cause both systemic and local reactions. Examples of local reactions include edema, erythema, induration, necrolic ulcers, pain, pruritis, and vesicles. The severity of the reaction is dependent on a variety of factors including the source of the venom (e.g. Loxosceles spider, box jellyfish, fire ant), the amount of venom injected, the location of the bite or sting (e.g. arm, thigh), and prior exposure to the venom. A variety of treatments have been used including analgesics, antibiotics, antivenoms, corticosteroids, Dapsone, and hyperbaric oxygen. In those
instances where the initial dermal lesion progresses to dcπnonccrosis, surgical intervention is often necessary. There is a continuing need for new treatments and in particular for treatments that will prevent dermonecrosis.
Summary of the Invention
The present invention relates to a method of treating dermal lesions caused by envenomation comprising applying a therapeutically effective amount of an immune response modifier compound selected from the group consisting of imidazoquinoline amines, imidazopyridine amines, 6,7-fused cycloalkylimidazopyridine amines, imidazonaphthyridine amines, tetrahydroimidazonaphthyridine amines, oxazolopyridine amines, oxazoloquinoline amines, thiazolopyridine amines, thiazoloquinoline amines and 1,2-bridged imidazoquinoline amines to the site of the lesion.
The present invention also provides a method of preventing dermonecrosis caused by envenomation comprising applying a therapeutically effective amount of an immune response modifier compound selected from the group consisting of imidazoquinoline amines, imidazopyridine amines, 6,7-fused cycloalkylimidazopyridine amines, imidazonaphthyridine amines, tetrahydroimidazonaphthyridine amines, oxazolopyridine amines, oxazoloquinoline amines, thiazolopyridine amines, thiazoloquinoline amines and 1,2-bridged imidazoquinoline amines to the site of the envenomation.
Detailed Description of the Invention
As used herein the term "envenomation" means injection of a poisonous material (venom) by sting, spine, fang, tooth, or other venom delivery apparatus.
Immune response modifier (IRM) compounds that are useful in practicing the methods of the present invention are selected from the group consisting of imidazoquinoline amines, imidazopyridine amines, 6,7-fused cycloalkylimidazopyridine amines, imidazonaphthyridine amines, tetrahydroimidazonaphthyridine amines, oxazolopyridine amines, oxazoloquinoline amines, thiazolopyridine amines, thiazoloquinoline amines and 1,2-bridged imidazoquinoline amines. Such compounds and methods for preparing them are disclosed in, for example, U.S. Patent Nos. 4,689,338;
5,389,640; 5,268,376; 4,929,624; 5,266,575; 5,352,784; 5,494,916; 5,482,936; 5,395,937; 5,175,296; 5,693,811; 5,741,908; 5, 756,747; 6,110,929; 4,988,815; 5,376,076; 6,083,505;
6,039,969; and International Publications WO 99/29693; WO 00/76505; WO 00/76518 and WO 00/76518. The entire disclosure of each of these patents and patent applications is incorporated herein by reference.
Preferred IRM compounds for use in the practice of the methods of the invention include compounds of Formula I
wherein
Ri is selected from the group consisting of S and NR3, R2 is selected from the group consisting of hydrogen, straight and branched chain alkyl containing one to six carbon atoms, and alkoxyalkyl wherein the alkoxy moiety contains one to four carbon atoms and the alkyl moiety contains one to four carbon atoms; and
R3 is selected from the group consisting of straight and branched chain alkyl containing one to six carbon atoms and straight and branched chain hydroxy alkyl containing one to six carbon atoms; or a pharmaceutically acceptable salt thereof.
Preferred R groups include hydrogen, methyl, ethyl, propyl, butyl, and ethoxymethyl.
Preferred R3 groups include 2-methylpropyl and 2-hydroxy-2-methylpropyl. Particularly preferred IRM compounds include 4~amino-2-ethoxymethyl-α,α- dimethyl-lH-imidazo[4,5-c]quinoline-l-ethanol (resiquimod), 1 -(2-methylpropyl)- 1H- imidazo[4,5-c]quinolin-4-amine (imiquimod), 2-methylthiazolo[4,5-c]quinolin-4-amine, 2-ethylthiazolo[4,5-c]quinolin-4~amine, 2-propylthiazolo[4,5-c]quinolin-4-amine and 2- butylthiazolo[4,5-c]quinolin-4-amine. In the method of the invention a therapeutically effective amount of the IRM compound is applied. The term "therapeutically effective amount" means an amount sufficient to induce a therapeutic effect such as the amelioration of symptoms (e.g. pain, erythema diminution of lesions,) or the prevention of dermonecrosis. The specific amount
that will constitute a therapeutically effective amount will vary according to factors readily determined by those skilled in the art including the activity of the particular IRM compound being used, the particular formulation being administered, the duration of the administration and the frequency of the administration. Generally from about 1 μg to about 125 mg, preferably from about 10 μg to about 25 mg, of the IRM compound is applied to the dermal lesion.
Any conventional dosage form suitable for topical application may be used including creams, gels, lotions, ointments, sprays and transdermal patches. Preferred formulations include creams and gels. Suitable formulations are disclosed, for example, in U.S. Patents 5,238,944 and 5,939,090 and International Publication WO 00/40228, the disclosures of which are incorporated by reference herein.
The frequency and duration of administration can vary as needed for amelioration of symptoms and/or prevention of dermonecrosis. Treatment regimens may include administration from twice per day to once per week, preferably two to three times per week, for at least one week, preferably for two to three weeks.
There are many venomous creatures whose bite or sting causes local reactions in humans. Examples of such creatures include, for example, arthropods such as arachnids (e.g., scorpions, spiders) and insects of the order Hymenoptera (e.g., bees, wasps, ants), and marine animals such as jellyfish, stone fish, stingrays, and blue ringed octopus. The venom of some species is known to cause dermal lesions dial can progress lo dermonecrosis. Examples of such species include Loxosceles spiders (L. reclusa, L. deserta, L. laeta), hobo spiders (Tegenaria spp), yellow sac spiders (Cheiracanthium spp.), fire ants (Solenopsis invicta), and jellyfish (Chironex flecked, Carybdea alata, Cassiopea andromeda, Aurelia auήta). Venoms are frequently complex mixtures of a variety of substances. Substances that have been identified include enzymes e.g. phospholipases, hyaluronidases, cholinesterases; alkaloids e.g. methyl-N-piperidine; proteins e.g. melittin; and peptides. The particular constituents will depend on the source of the venom. When envenomation occurs a number of different types of epithelial and endothelial cells are exposed to the venom. These cells are capable of synthesizing and releasing a wide variety of chemokines and cytokines in response to a variety of stimuli. For example, it has been shown in vitro that Loxosceles deserta venom induces endothelial and epithelial cells to
secrete both α and β chemokines. The release of chemokines and cytokines triggers additional events such as the attraction of neutrophils to the site of envenomation. While some of the local skin reactions that are manifested as a result of envenomation such as edema and erythema are caused directly by constituents of the venom due to the hemolytic action of various enzymes, it has been hypothesized that dermonecrosis may be due to an immune response.
While not wishing to be bound by theory, it is believed that effects of the IRM compound overwhelm the local physiological effects of the venom. This may occur by modifying the qualitative properties of the local soluble mediators of inflammation such that signaling for ncutr phil activation and dcgraπulation is inhibited. In addition, the early aggregation of neutrophils in dermal blood vessels may be diffused by IRM compound induced cytokines by stimulating the migration of neutrophils out of local vasculature and into surrounding tissue. Thus, if activated neutrophils are no longer aggregated in the discrete focal area of the site of envenomation, the amount of central necrosis may be inhibited. In essence, the venom induced "immune dysregulation" may be overcome by the immune stimulation provided by the IRM compound.
Example Treatment of Loxosceles reclusa envenomation with Imiquimod 5% Cream
Background
A privatized correctional facility in Texas experienced a cluster of spider bite cases due to L. reclusa shortly following the receipt of a shipment of used mattresses from a local county jail. Spiders may have inhabited the mattresses when they were stored for several weeks in a dark shed out behind the facility. Following the first several cases, fumigation with a synthetic pyrethroid (PT 1200, resmethrin) was performed. While this agent is considered effective against L. reclusa, the spiders must generally be contacted directly, and unhatched eggs are less susceptible.
The diagnosis of loxoscelism in these cases was made by exclusion. No spiders were recovered despite the use of glue traps, although in one case, a "brown spider" dropped from the ceiling of a shower onto the breast of a female patient, who brushed the spider away after sustaining a bite. The following aspects of these cases favor a diagnosis
of L. reclusa envenomation: the spider is endemic to the area; the bites occurred mostly at night and were characterized by lack of immediate pain. Blanching and cyanosis slowly developed at the central core, with spreading erythema and progression to dermonecrosis. Other insects are known to inflict bites with similar clinical findings but can be excluded on the grounds that they are not found in Texas (various tarantulas, Australian funnel-web spiders (Atrax spp.), "hobo spiders" (Tegeneria spp.); they form characteristic webs not found in the facility (yellow sac spiders (Chiracanthiwn spp.), black-and-yellow orb weavers (Argiope spp.); or they bite during the day ("jumping spider" (Phidippus audax)). Pliidippus species are very aggressive and bite commonly, but they inflict only slightly painful bites resulting in erythematous papules or small urticarial wheals. The only alternative suspect is Latrodectus mactans ("Southern black widow"). This spider is shy in behavior, similar to L. reclusa, and bites often go unnoticed until a red papule progresses to a larger halo or target lesion up to 2 cm in diameter. Unlike the L, reclusa bite however, skin manifestations are minimal. Victims are more likely to experience muscle spasms and cramping within hours of envenomation, together with weakness of the legs and tightness of the chest. These clinical findings were absent in the cases reported here.
Methods Patients were seen in the facility clinic on Ihc day they complained of a painful lesion. Most patients related a history of discovering the lesion upon awakening in the morning. The treatment of the first 12 consecutive cases, occurring over a 5 month period, consisted of a single intramuscular dose of ceftriaxone 1 gm and oral dicloxicillin 500 mg bid x 10 days, plus either topical triamcinolone 0.1% applied bid, topical papain-urea- chlorophyllin copper complex sodium debriding-healing ointment (Panafil™) applied daily, or daily topical becaplermin (rh-PDGF-BB) 0.01% gel (Regranex™). Where necessary and appropriate, patients were transported to the local University Medical Center for surgical debridement of necrotic lesions.
A consecutive series of 7 bites on 5 patients were treated with imiquimod 5% cream (available under the tradename ALDARA from 3M Pharmaceuticals, St. Paul, MN,
USA) applied by the clinic staff, three times per week (typically Monday, Wednesday and Friday) for two weeks. Sufficient cream was used to cover the area of erythema, rubbing
the cream gently until it "vanished" as per labeled instructions. In addition, a single intramuscular dose of ceftriaxone 1 gm was given together with oral dicloxicillin, 500 mg bid for 10 days. Patients were re-examined by a physician at 7, 14 and 28 days following initiation of therapy.
Results
The first 12 patients, managed using conventional therapy, presented with tender to painful lesions consisting of a central core of induration and blanching, surrounded by 3-8 cm of erythema. Among these, 7 progressed to tissue necrosis within 1 week after the bite, all of whom were referred for surgical debridement. One patient developed a healing contracture of the forearm which necessitated surgical release. Healing occun'ed by secondary intention over several months following the bites.
Seven consecutive bites occurring in 5 patients were treated with imiquimod.
These cases are summarized in the Table below. Presenting signs and symptoms were consistent with those recorded for patients treated by conventional means. Tenderness or pain, with erythema, characteristic blanching and firm induration were present in every case. In one case (L.S.), punctuate marks were noted at the center of the indurated area.
Pain relief was reported by all patients within 1-2 days following the first dose of imiquimod. Marked improvement in both induration and erythema was noted by day 7, with full resolution in all but one case by day 14. In patient Y.C., erythema was noted to be cleared at the day 7 visit but developed again by day 14. The reappearance of erythema is presumed to be secondary to imiquimod
Patients C.R. and L.S. each sustained two bites. In the case of L.S., the first bite was resolved 9 days after it occurred. The second bite occurred 16 days after the first bite and resolved completely, with treatment, by the 5th day. The difference in clinical course may have been due to differences in the age of the spider, the sex of the spider (females inject greater volumes of venom), or an acquired immunity following the first bite.
Necrosis did not develop in any of the imiquimod treated cases. No residual scarring or pigmentation changes were noted at the day 28 follow-up visit. The probability of observing 0 out of 7 consecutive cases with no necrosis, given the underlying historical rate of 7/12 (0.583), is quite low based on a binomial probability distribution (p=0.002) or a Chi-square analysis (p=0.01).
Claims (1)
- WHAT IS CLAIMED IS:1. A method of treating dermal lesions caused by envenomation comprising applying a therapeutically effective amount of an immune response modifier compound selected from the group consisting of imidazoquinoline amines, imidazopyridine amines, 6,7-fused cycloalkylimidazopyridine amines, imidazonaphthyridine amines, tetrahydroimidazonaphthyridine amines, oxazolopyridine amines, oxazoloquinoline amines, thiazolopyridine amines, thiazoloquinoline amines and 1,2-bridged imidazoquinoline amines to the site of the lesion.2. The method of Claim 1 wherein the immune response modifier compound is a compound of Formula II wherein Ri is selected from the group consisting of S and NR3,R2 is selected from the group consisting of hydrogen, straight and branched chain alkyl containing one to six carbon atoms, and alkoxyalkyl wherein the alkoxy moiety contains one to four carbon atoms and the alkyl moiety contains one to four carbon atoms; and R3 is selected from the group consisting of straight and branched chain alkyl containing one to six carbon atoms and straight or branched chain hydroxy alkyl containing one to six carbon atoms; or a pharmaceutically acceptable salt thereof.The method of Claim 2 wherein Rι is NR34. The method of Claim 2 wherein Rj is S.5. The method of Claim 2 wherein R2 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl, and ethoxymethyl.6. The method of Claim 2 wherein R3 is selected from the group consisting of 2- methylpropyl and 2-hydroxy-2-methylpropyl.7. The method of Claim 2 wherein the IRM compound is selected from the group consisting of 4-amino-2-ethoxymethyl-α,α-dimethyl- 1 H-imidazo[4,5-c]quinoline- 1 - ethanol, l-(2-methylpropyl)-lH-imidazo[4,5-c]quinolin-4-amine, 2-methylthiazolo[4,5- c]quinolin-4-amine, 2-ethylthiazolo[4,5-c]quinolin-4-amine, 2-propylthiazolo[4,5- c]quinolin-4-amine and 2-butylthiazolo[4,5-c]quinolin-4-amine.8. The method of Claim 1 wherein the immune response modifier compound is applied via a cream or a gel.9. The method of Claim 1 wherein the source of the envenomation is an arthopod.10. The method Claim 9 wherein the arthopod is a spider.11. The method of Claim 9 wherein the arthodpod is an insect of the orderΗymenoptera.12. The method of Claim 1 wherein the source of envenomation is a marine animal.13. The method of Claim 12 wherein the marine animal is a jellyfish.14. A method of preventing dermonecrosis caused by envenomation comprising applying a therapeutically effective amount of an immune response modifier compound selected from the group consisting of imidazoquinoline amines, imidazopyridine amines, 6,7-fused cycloalkylimidazopyridine amines, imidazonaphthyridine amines, tetrahydroimidazonaphthyridine amines, oxazolopyridine amines, oxazoloquinoline amines, thiazolopyridine amines, thiazoloquinoline amines and 1,2-bridged imidazoquinoline amines to the site of the envenomation.15. The method of Claim 14 wherein the immune response modifier compound is a compound of Formula II whereinRi is selected from the group consisting of S and NR3,R2 is selected from the group consisting of hydrogen, straight and branched chain alkyl containing one to six carbon atoms, and alkoxyalkyl wherein the alkoxy moiety contains one to four carbon atoms and the alkyl moiety contains one to four carbon atoms; andR3 is selected from the group consisting of straight and branched chain alkyl containing one to six carbon atoms and straight or branched chain hydroxy alkyl containing one to six carbon atoms; or a pharmaceutically acceptable salt thereof.16. The method of Claim 15 wherein Ri is NR3.17. The method of Claim 15 wherein R( is S.18. The method of Claim 15 wherein R2 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl, and ethoxymethyl.19. The method of Claim 15 wherein R3 is selected from the group consisting of 2- methylpropyl and 2-hydroxy-2-methyIpropyl.20. The method of Claim 15 wherein the IRM compound is selected from the group consisting of 4-amino-2-ethoxymethyl-α,α-dimethyl-lH-imidazo[4,5-c]quinoline-l- ethanol, l-(2-methylpropyl)-lH-imidazo[4,5-c]quinolin-4-amine, 2-methylthiazolo[4,5- c]quinolin-4-amine, 2-ethylthiazolo[4,5-c]quinolin-4-amine, 2-propylthiazolo[4,5- c]quinolin-4-amine and 2-butylthiazolo[4,5-c]quinolin-4-amine.21. The method of Claim 14 wherein the immune response modifier compound is applied via a cream or a gel.22. The method of Claim 14 wherein the source of the envenomation is an arthopod.23. The method Claim 22 wherein the arthopod is a spider.24. The method of Claim 22 wherein the arthodpod is an insect of the order Ηymenoptera.25. The method of Claim 14 wherein the source of envenomation is a marine animal.26. The method of Claim 25 wherein the marine animal is a jellyfish.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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US19312000P | 2000-03-30 | 2000-03-30 | |
US60/193,120 | 2000-03-30 | ||
US09/820,420 US6894060B2 (en) | 2000-03-30 | 2001-03-29 | Method for the treatment of dermal lesions caused by envenomation |
US09/820,420 | 2001-03-29 | ||
PCT/US2001/010291 WO2001074343A2 (en) | 2000-03-30 | 2001-03-30 | Method for the treatment of dermal lesions caused by envenomation |
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AU2001251146A1 true AU2001251146A1 (en) | 2002-01-03 |
AU2001251146B2 AU2001251146B2 (en) | 2004-12-16 |
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AU2001251146A Ceased AU2001251146B2 (en) | 2000-03-30 | 2001-03-30 | Method for the treatment of dermal lesions caused by envenomation |
AU5114601A Pending AU5114601A (en) | 2000-03-30 | 2001-03-30 | Method for the treatment of dermal lesions caused by envenomation |
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Families Citing this family (135)
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 (en) * | 1997-12-11 | 2004-07-15 | Міннесота Майнінг Енд Мануфакчурінг Компані | Imidazonaphthyridines and use thereof to induce the biosynthesis of cytokines |
US6756382B2 (en) * | 1999-06-10 | 2004-06-29 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
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 |
US6916925B1 (en) | 1999-11-05 | 2005-07-12 | 3M Innovative Properties Co. | Dye labeled imidazoquinoline compounds |
JP3436512B2 (en) * | 1999-12-28 | 2003-08-11 | 株式会社デンソー | Accelerator device |
US6525064B1 (en) | 2000-12-08 | 2003-02-25 | 3M Innovative Properties Company | Sulfonamido substituted imidazopyridines |
US6664265B2 (en) | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
US6677347B2 (en) | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamido ether substituted imidazoquinolines |
US6545016B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Amide substituted imidazopyridines |
UA74852C2 (en) | 2000-12-08 | 2006-02-15 | 3M Innovative Properties Co | Urea-substituted imidazoquinoline ethers |
US6545017B1 (en) * | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Urea substituted imidazopyridines |
US6677348B2 (en) | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Aryl ether substituted imidazoquinolines |
US6664264B2 (en) | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
US6660735B2 (en) | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Urea substituted imidazoquinoline ethers |
US6667312B2 (en) * | 2000-12-08 | 2003-12-23 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
US20060142202A1 (en) * | 2000-12-08 | 2006-06-29 | 3M Innovative Properties Company | Compositions and methods for targeted delivery of immune response modifiers |
US7226928B2 (en) * | 2001-06-15 | 2007-06-05 | 3M Innovative Properties Company | Methods for the treatment of periodontal disease |
US20040014779A1 (en) * | 2001-11-16 | 2004-01-22 | 3M Innovative Properties Company | Methods and compositions related to IRM compounds and toll-like recptor pathways |
WO2004080430A2 (en) * | 2003-03-13 | 2004-09-23 | 3M Innovative Properties Company | Methods of improving skin quality |
EP1450804B9 (en) | 2001-11-29 | 2009-04-01 | 3M Innovative Properties Company | Pharmaceutical formulations comprising an immune response modifier |
CA2365732A1 (en) | 2001-12-20 | 2003-06-20 | Ibm Canada Limited-Ibm Canada Limitee | Testing measurements |
US6677349B1 (en) | 2001-12-21 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
EP1478327B1 (en) * | 2002-02-22 | 2015-04-29 | Meda AB | Method of reducing and treating uvb-induced immunosuppression |
EP1376872B1 (en) * | 2002-05-07 | 2007-10-10 | Schott Ag | Illumination device for touchscreens |
AU2003237386A1 (en) | 2002-06-07 | 2003-12-22 | 3M Innovative Properties Company | Ether substituted imidazopyridines |
ATE488246T1 (en) | 2002-08-15 | 2010-12-15 | 3M Innovative Properties Co | IMMUNO-STIMULATORY COMPOSITIONS AND METHODS FOR STIMULATING AN IMMUNE RESPONSE |
JP2006503068A (en) | 2002-09-26 | 2006-01-26 | スリーエム イノベイティブ プロパティズ カンパニー | 1H-Imidazo dimer |
AU2003301052A1 (en) | 2002-12-20 | 2004-07-22 | 3M Innovative Properties Company | Aryl / hetaryl substituted imidazoquinolines |
EP2572715A1 (en) | 2002-12-30 | 2013-03-27 | 3M Innovative Properties Company | Immunostimulatory Combinations |
WO2004071459A2 (en) * | 2003-02-13 | 2004-08-26 | 3M Innovative Properties Company | Methods and compositions related to irm compounds and toll-like receptor 8 |
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US7309326B2 (en) * | 2003-11-18 | 2007-12-18 | Icu Medical, Inc. | Infusion set |
JP4891088B2 (en) * | 2003-11-25 | 2012-03-07 | スリーエム イノベイティブ プロパティズ カンパニー | Substituted imidazo ring systems and methods |
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WO2006086634A2 (en) | 2005-02-11 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted imidazo[4,5-c] ring compounds and methods |
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JP2008533148A (en) | 2005-03-14 | 2008-08-21 | スリーエム イノベイティブ プロパティズ カンパニー | Treatment method for actinic keratosis |
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AU2006232375A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | 1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases |
US20080193474A1 (en) * | 2005-04-25 | 2008-08-14 | Griesgraber George W | Immunostimulatory Compositions |
JP2009507856A (en) | 2005-09-09 | 2009-02-26 | コーリー ファーマシューティカル グループ,インコーポレイテッド | Amide and carbamate derivatives of N- {2- [4-amino-2- (ethoxymethyl) -1H-imidazo [4,5-c] quinolin-1-yl] -1,1-dimethylethyl} methanesulfonamide and Method |
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EP1948173B1 (en) | 2005-11-04 | 2013-07-17 | 3M Innovative Properties Company | Hydroxy and alkoxy substituted 1h-imidazoquinolines and methods |
US7892216B2 (en) * | 2006-02-07 | 2011-02-22 | Icu Medical, Inc. | Infusion set |
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WO2007106854A2 (en) | 2006-03-15 | 2007-09-20 | Coley Pharmaceutical Group, Inc. | Hydroxy and alkoxy substituted 1h-imidazonaphthyridines and methods |
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ES2393761T3 (en) * | 2006-07-14 | 2012-12-27 | Stiefel Research Australia Pty Ltd | Pharmaceutical fatty acid foam |
WO2008030511A2 (en) | 2006-09-06 | 2008-03-13 | Coley Pharmaceuticial Group, Inc. | Substituted 3,4,6,7-tetrahydro-5h, 1,2a,4a,8-tetraazacyclopenta[cd]phenalenes |
US20080149123A1 (en) * | 2006-12-22 | 2008-06-26 | Mckay William D | Particulate material dispensing hairbrush with combination bristles |
WO2008098232A1 (en) | 2007-02-08 | 2008-08-14 | Graceway Pharmaceuticals, Llc | Methods of treating dermatological disorders and inducing interferon biosynthesis with shorter durations of imiquimod therapy |
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US20100160368A1 (en) | 2008-08-18 | 2010-06-24 | Gregory Jefferson J | Methods of Treating Dermatological Disorders and Inducing Interferon Biosynthesis With Shorter Durations of Imiquimod Therapy |
RS58566B1 (en) | 2008-12-19 | 2019-05-31 | Medicis Pharmaceutical Corp | Lower dosage strength imiquimod formulations and short dosing regimens for treating actinic keratosis |
JP5738839B2 (en) | 2009-04-01 | 2015-06-24 | ウイラ アイピー プロプライエタリー リミテッド | Multiple dose packages, courses of treatment, and methods of treatment for delivering predetermined multiple doses of a drug |
EA025993B1 (en) | 2009-07-13 | 2017-02-28 | Медисис Фармасьютикал Корпорейшн | Lower dosage strength imiquimod formulations and short dosing regimens for treating genital and perianal warts |
DK2584900T3 (en) | 2010-06-25 | 2019-04-01 | Medicis Pharmaceutical Corp | Combination therapy with cryosurgery and low-dose imiquimod for the treatment of actinic keratosis |
RS55819B1 (en) | 2010-08-17 | 2017-08-31 | 3M Innovative Properties Co | Lipidated immune response modifier compound compositions, formulations, and methods |
CA2838158C (en) | 2011-06-03 | 2019-07-16 | 3M Innovative Properties Company | Heterobifunctional linkers with polyethylene glycol segments and immune response modifier conjugates made therefrom |
BR112013031039B1 (en) | 2011-06-03 | 2020-04-28 | 3M Innovative Properties Co | hydrazine compounds 1h-imidazoquinoline-4-amines, conjugates made from these compounds, composition and pharmaceutical composition comprising said compounds and conjugates, uses thereof and method of manufacturing the conjugate |
US20130023736A1 (en) | 2011-07-21 | 2013-01-24 | Stanley Dale Harpstead | Systems for drug delivery and monitoring |
WO2013040447A2 (en) | 2011-09-14 | 2013-03-21 | Medicis Pharmaceutical Corporation | Combination therapy with low dosage strength imiquimod and photodynamic therapy to treat actinic keratosis |
WO2013162828A1 (en) | 2012-04-27 | 2013-10-31 | The United States Of America, As Represented By The Secretary, Department Of Health & Human Services | Use of cpg oligonucleotides co-formulated with an antibiotic to accelarate wound healing |
BR102013031043B1 (en) * | 2013-12-02 | 2018-03-13 | Fundação Butantan | USE OF CHEMICAL COMPOUNDS ABLE TO INHIBIT THE TOXIC ACTION OF SPXOMYELINASES D FROM LOXOSCEL SPIDEN POISON AND PHARMACEUTICAL COMPOSITION UNDERSTANDING THE COMPOUND COMPOUNDS |
US10232048B1 (en) | 2014-11-18 | 2019-03-19 | Divine Api-Logics, LLC | Apitherapy method and composition |
JP7265989B2 (en) | 2016-10-25 | 2023-04-27 | ウロゲン ファーマ リミテッド | Immunomodulatory treatment of body cavities |
EP3728255B1 (en) | 2017-12-20 | 2022-01-26 | 3M Innovative Properties Company | Amide substituted imidazo[4,5-c]quinoline compounds with a branched chain linking group for use as an immune response modifier |
Family Cites Families (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3314941A (en) * | 1964-06-23 | 1967-04-18 | American Cyanamid Co | Novel substituted pyridodiazepins |
US3917624A (en) * | 1972-09-27 | 1975-11-04 | Pfizer | Process for producing 2-amino-nicotinonitrile intermediates |
IL73534A (en) * | 1983-11-18 | 1990-12-23 | Riker Laboratories Inc | 1h-imidazo(4,5-c)quinoline-4-amines,their preparation and pharmaceutical compositions containing certain such compounds |
ZA848968B (en) * | 1983-11-18 | 1986-06-25 | Riker Laboratories Inc | 1h-imidazo(4,5-c)quinolines and 1h-imidazo(4,5-c)quinolin-4-amines |
US5238944A (en) * | 1988-12-15 | 1993-08-24 | Riker Laboratories, Inc. | Topical formulations and transdermal delivery systems containing 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine |
US5037986A (en) * | 1989-03-23 | 1991-08-06 | Minnesota Mining And Manufacturing Company | Olefinic 1H-imidazo[4,5-c]quinolin-4-amines |
US4929624A (en) * | 1989-03-23 | 1990-05-29 | Minnesota Mining And Manufacturing Company | Olefinic 1H-imidazo(4,5-c)quinolin-4-amines |
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 |
US5268376A (en) * | 1991-09-04 | 1993-12-07 | Minnesota Mining And Manufacturing Company | 1-substituted 1H-imidazo[4,5-c]quinolin-4-amines |
US5266575A (en) * | 1991-11-06 | 1993-11-30 | Minnesota Mining And Manufacturing Company | 2-ethyl 1H-imidazo[4,5-ciquinolin-4-amines |
IL105325A (en) | 1992-04-16 | 1996-11-14 | Minnesota Mining & Mfg | Immunogen/vaccine adjuvant composition |
US5352784A (en) * | 1993-07-15 | 1994-10-04 | Minnesota Mining And Manufacturing Company | Fused cycloalkylimidazopyridines |
ATE195735T1 (en) * | 1993-07-15 | 2000-09-15 | Minnesota Mining & Mfg | IMIDAZO (4,5-C)PYRIDINE-4-AMINE |
US5648516A (en) * | 1994-07-20 | 1997-07-15 | Minnesota Mining And Manufacturing Company | Fused cycloalkylimidazopyridines |
US5644063A (en) * | 1994-09-08 | 1997-07-01 | Minnesota Mining And Manufacturing Company | Imidazo[4,5-c]pyridin-4-amine intermediates |
US5482936A (en) * | 1995-01-12 | 1996-01-09 | Minnesota Mining And Manufacturing Company | Imidazo[4,5-C]quinoline amines |
US5585612A (en) * | 1995-03-20 | 1996-12-17 | Harp Enterprises, Inc. | Method and apparatus for voting |
JPH09208584A (en) | 1996-01-29 | 1997-08-12 | Terumo Corp | Amide derivative, pharmaceutical preparation containing the same, and intermediate for synthesizing the same |
US5741908A (en) | 1996-06-21 | 1998-04-21 | Minnesota Mining And Manufacturing Company | Process for reparing imidazoquinolinamines |
EP0938315B9 (en) * | 1996-10-25 | 2008-02-20 | Minnesota Mining And Manufacturing Company | Immune response modifier compounds for treatment of th2 mediated and related diseases |
US5939090A (en) * | 1996-12-03 | 1999-08-17 | 3M Innovative Properties Company | Gel formulations for topical drug delivery |
US6069149A (en) * | 1997-01-09 | 2000-05-30 | Terumo Kabushiki Kaisha | Amide derivatives and intermediates for the synthesis thereof |
UA67760C2 (en) | 1997-12-11 | 2004-07-15 | Міннесота Майнінг Енд Мануфакчурінг Компані | Imidazonaphthyridines and use thereof to induce the biosynthesis of cytokines |
US6110929A (en) * | 1998-07-28 | 2000-08-29 | 3M Innovative Properties Company | Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof |
JP2000119271A (en) | 1998-08-12 | 2000-04-25 | Hokuriku Seiyaku Co Ltd | 1h-imidazopyridine derivative |
CA2361936C (en) | 1999-01-08 | 2009-06-16 | 3M Innovative Properties Company | Formulations comprising imiquimod or other immune response modifiers for treating mucosal conditions |
US6541485B1 (en) | 1999-06-10 | 2003-04-01 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
US6451810B1 (en) | 1999-06-10 | 2002-09-17 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
-
2001
- 2001-03-29 US US09/820,420 patent/US6894060B2/en not_active Expired - Fee Related
- 2001-03-30 WO PCT/US2001/010291 patent/WO2001074343A2/en active IP Right Grant
- 2001-03-30 AU AU2001251146A patent/AU2001251146B2/en not_active Ceased
- 2001-03-30 AU AU5114601A patent/AU5114601A/en active Pending
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