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(12) United States Patent (10) Patent No.: US 9,655,867 B2 Spakevicius Et Al

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(12) United States Patent (10) Patent No.: US 9,655,867 B2 Spakevicius Et Al US0096.55867B2 (12) United States Patent (10) Patent No.: US 9,655,867 B2 Spakevicius et al. (45) Date of Patent: May 23, 2017 (54) ANALGESC COMPOSITIONS (58) Field of Classification Search CPC .......... A61K 31/08: A61K 31/02: A61 K9/70; (71) Applicant: VAPOGENIX, INC., Houston, TX A61K 47/10; A61K 47/12: A61K 47/20; (US) A61K 47/34: A61K 47/38 (72) Inventors: Danguole Spakevicius, Houston, TX (Continued) (US); Heather Giles, Houston, TX (US); Terry Farmer, Houston, TX (56) References Cited (US) U.S. PATENT DOCUMENTS (73) Assignee: Vapogenix, Inc., Houston, TX (US) 7,736,537 B1 6/2010 Zastrow et al. (*) Notice: Subject to any disclaimer, the term of this 2011/O159078 A1 6, 2011 Burton et al. patent is extended or adjusted under 35 (Continued) U.S.C. 154(b) by 0 days. FOREIGN PATENT DOCUMENTS (21) Appl. No.: 14/775,584 GB 154.7225 A 6, 1979 WO 2008O36858 A2 3, 2008 (22) PCT Fed: Mar. 14, 2014 (Continued) (86) PCT No.: PCT/US2O14/028169 S 371 (c)(1), OTHER PUBLICATIONS (2) Date: Sep. 11, 2015 International Search Report (ISA/US) dated Sep. 30, 2014 for PCT PCT Pub. No.: WO2O14f143964 International Application No. PCT/US2014/028169, filed Mar. 14, (87) 2014. PCT Pub. Date: Sep. 18, 2014 (Continued) (65) Prior Publication Data Primary Examiner — T. Victor Oh US 2016/0022603 A1 Jan. 28, 2016 (74) Attorney, Agent, or Firm — Saul Ewing LLP: Related U.S. Application Data Kathryn Doyle; Domingos J. Silva (60) Provisional application No. 61/814,485, filed on Apr. (57) ABSTRACT 22, 2013, provisional application No. 61/792.383, The present invention provides compositions useful in filed on Mar. 15, 2013. reducing or preventing pain in a Subject in need thereof. In certain embodiments, the compositions comprise a haloge (51) Int. C. nated volatile compound. The present invention further A6 IK3I/08 (2006.01) includes a method of reducing or preventing pain in a subject A6 IK3I/02 (2006.01) in need thereof, the method comprising administering to the (Continued) subject a therapeutically effective amount of at least one (52) U.S. C. composition of the invention. Dosing regimens contem CPC ............ A61 K3I/08 (2013.01); A61K 9/0014 plated within the invention include one-time administration, (2013.01); A61K 9/06 (2013.01); A61K 9/08 continuous administration or periodic administration. (2013.01); (Continued) 31 Claims, 4 Drawing Sheets 993 &8. 8 X) S 880 99t 8 US 9,655,867 B2 Page 2 (51) Int. Cl. (56) References Cited A6 IK 47/10 (2017.01) A6 IK 47/20 (2006.01) U.S. PATENT DOCUMENTS A6 IK 47/38 (2006.01) 2012, 0071533 A1 3, 2012 Vontz et al. A 6LX 9/70 (2006.01) 2012/0171281 A1 7/2012 Spakevicius et al. A6 IK 47/12 (2006.01) A6 IK 47/34 (2017.01) FOREIGN PATENT DOCUMENTS A6 IK 9/00 (2006.01) WO 2009 117489 A1 9, 2009 A6 IK 47/22 (2006.01) WO 2012.177840 A1 12/2012 A6 IK 9/06 (2006.01) WO 2013OO4838 A1 1, 2013 st W 08: OTHER PUBLICATIONS (52) U.S. Cl. Ardente, et al., “Vehicle Effects on in vitro Transdermal: . Absorption CPC .............. A61K 9/70 (2013.01); A61K 9/7023 Stins N But ise, thesists (2013.01);(2013-0). A61K 47/1231/02 (201301):(2013.01); A61K461s 47/204AO SevofluraneNE"S", on Venous "S",Leg Ulcer with"EEE Intractable Pain'. (2013.01); A61K 4 7/22 (2013.01); A61K 47/32 Phlebologie, vol. 2, 2011, pp. 95-97. (2013.01); A61K 47/34 (2013.01); A61K 47/38 Inoue, S., et al., “Mild Hypothermia can Enhance Pial Arteriolar (2013.01) Vasodilation Induced by Isoflurane and Sevoflurane in Cats'. Criti cal Care Medicine, vol. 30, No. 8, 2002, pp. 1863-1869. (58) Field of Classification Search Smith, J.M., et al., “Isoflurane Anesthesia in the African Clawed USPC .......................................................... 514/722 Frog (Xenopus laevis). Contemporary Topics in Laboratory Animal See application file for complete search history. Science, vol. 39, No. 6, 2000, pp. 39-42. U.S. Patent May 23, 2017 Sheet 1 of 4 US 9,655,867 B2 og gag Ooo gz Oog 000 002 000 gll Oog 00a girl gee Oog Oog gas Oood g! Oog Oool ge gloool gzi Ocol Oooz Oga Oog 003 Ogal 000 Oga Oog Oogical Gr, gll 00 000 Oog Ooe Ooo ocol 009 gz Oog Ooz U.S. Patent US 9,655,867 B2 zza Coog lefjos O 7. E. O 6. 8. A. 9. G 7. eflyOS E. e6]ueon|Sue O g O lefjos SO eggos usunuo ucanics of jos GO > 70 e6 JOS U.S. Patent May 23, 2017 Sheet 3 of 4 US 9,655,867 B2 FIG 2 Mean responses to pinprick following 10 minute topical application of formulations (ESEM). A) Formulation 212 (n 8), B) Formulation 216 (n A Formulation 212 Sw 8 t S s s SS s | ww.treated N. & control Time after removal of drug Time after removal of drug U.S. Patent May 23, 2017 Sheet 4 of 4 US 9,655,867 B2 FIG, 3 Winsisti S. wŠwsi fate US 9,655,867 B2 1. 2 ANALGESC COMPOSITIONS also the second most common cause of “worst pain’. Pedi atric inpatients report IV line placement as the leading cause CROSS-REFERENCE TO RELATED of procedure-related pain in the hospital, on par with post APPLICATIONS Surgical pain. Venipuncture causes not only moderate or severe pain in a significant number of pediatric inpatients, The present application is a 35 U.S.C. S371 national phase but also elevated levels of pre-procedural and procedural application of International Application No. PCT/US2014/ distress. Young children, even neonates, have highly refined 028169, filed Mar. 14, 2014, and published under PCT pain-sensing systems. Continuous exposure to such pain can Article 21(2) in English, which claims priority under 35 cause maladaptive pain response as an adult, but also the U.S.C. S 119(e) to U.S. Provisional Applications No. 61/792, 10 painful memory of Such events can have significant psycho 383, filed Mar. 15, 2013, and No. 61/814,485, filed Apr. 22, logical and physiological ramifications on later painful epi 2013, all of which applications are incorporated herein by sodes. reference in their entireties. Thus, considerable attention has been focused on the issue of preventing or reducing venous access pain in children. In BACKGROUND OF THE INVENTION 15 fact, national and international organizations have proposed clinical guidelines recommending the use of local anesthet Pain is defined as an unpleasant sensory and emotional ics in Such cases, and Such guidelines have been included in experience. Millions of people Suffer from pain, ranging the hospital-accreditation process. Unfortunately, compli from minor headaches to debilitating chronic pain. Acute ance with these guidelines is low. One of the major barriers pain may be associated with a medical procedure or injury. to implementing the guidelines is the slow onset of action Chronic pain may be associated with conditions such as and resultant treatment delays associated with existing medi cancer, HIV or diabetes. Currently available drugs used to cations. treat pain have significant associated adverse effects, such as Currently, there is no pain medication that alleviates pain nausea, vomiting, tolerance, constipation, dyspepsia, myo associated with minor procedures quickly, cost-effectively, cardial infarction, stroke and chemical dependence. 25 and topically. Current pharmaceutical products are virtually An analgesic (also known as a painkiller) is the general all based on lidocaine, while other local anesthetics cannot name for a drug used to relieve pain (achieve analgesia). easily penetrate intact human skin and cannot be used on Analgesic drugs act through various mechanisms on the large areas. Lidocaine-based creams take 45-60 minutes to peripheral and central nervous systems. They include par begin taking effect, reaching maximum effect at about 120 acetamol (p-acetylamino phenol, also known as acetamino 30 minutes, and this slow onset limits their use in clinical phen); the non-steroidal anti-inflammatory drugs (NSAIDs), Settings. such as the salicylates; opioid drugs, such as morphine and Further, current topical analgesics slow onset of action opium; and drugs for localized analgesia/anesthesia, Such as impedes their use for treating other procedural pain, Such as lidocaine and benzocaine. Analgesics are distinct from gen that associated with painful cosmetic and medical dermato eral anesthetics, which reversibly render a patient uncon 35 logical procedures (for example mole removal, skin biop scious and unaware of the Surroundings. Local anesthesia sies, Botox and fillers, aesthetic injections), with medical leads to loss of feeling, whereas analgesia decreases the injections (such as immunizations, and insulin administra sensation of pain. tion), with circumcision, heel sticks and other minor medical In choosing analgesics, the severity and response to procedures as well as with non-medical uses (such as tattoos, medication determines the choice of compound. The WHO 40 tattoo removal and piercings). pain ladder, originally developed in cancer-related pain, is An inhalational anesthetic possesses general anesthetic widely applied to find Suitable compounds in a stepwise properties and can be delivered via inhalation. Inhalational manner (Cancer pain relief and palliative care: Report of a anesthetics are administered by anesthetists through an WHO expert committee (1990). World Health Organization anesthesia mask, laryngeal mask airway or tracheal tube Technical Report Series, 804. Geneva, Switzerland: World 45 connected to some type of anesthetic vaporizer and an Health Organization, pp. 1-75). The choice of analgesic is anesthetic delivery system. Non-limiting examples of inha also determined by the type of pain: traditional analgesics lational anesthetics include volatile anesthetics (such as are less effective for neuropathic pain, and classes of drugs isoflurane, sevoflurane, desflurane or aliflurane) and anes not normally considered analgesics, such as tricyclic anti thetic gases (such as nitrous oxide or Xenon).
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