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WO2015115826A1 - Dérivé de benzoxazole à activité atténuant le prurit - Google Patents

Dérivé de benzoxazole à activité atténuant le prurit Download PDF

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Publication number
WO2015115826A1
WO2015115826A1 PCT/KR2015/000959 KR2015000959W WO2015115826A1 WO 2015115826 A1 WO2015115826 A1 WO 2015115826A1 KR 2015000959 W KR2015000959 W KR 2015000959W WO 2015115826 A1 WO2015115826 A1 WO 2015115826A1
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WO
WIPO (PCT)
Prior art keywords
formula
group
pruritus
lower alkyl
amino
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2015/000959
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English (en)
Korean (ko)
Inventor
박혜영
나흥식
백승근
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ewha Womans University
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Ewha Womans University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ewha Womans University filed Critical Ewha Womans University
Publication of WO2015115826A1 publication Critical patent/WO2015115826A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42—Oxazoles
    • A61K31/423—Oxazoles condensed with carbocyclic rings
    • 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

Definitions

  • the present invention relates to a novel benzoxazole derivative having a pruritic prevention, amelioration or therapeutic effect in a skin disease and a method for producing the same.
  • a therapeutic agent for pruritus skin-cooling agents, steroids, anesthetics, and antihistamines are used.
  • Calamine or menthol lotions cool the skin and relieve pruritus, but have only a very temporary effect.
  • Steroids have vasoconstrictive, anti-proliferative, immunosuppressive and anti-inflammatory effects, and have immediate effects on relieving pruritus, especially in autoimmune diseases such as atopic dermatitis, but are limited in their long-term use due to severe side effects.
  • Phenol lotion and capsaicin paralyze the sensation and relieve pruritus, but the effect is temporary and can cause skin irritation.
  • Antihistamines are mainly used as drugs to eat.
  • lower alkyl mercapto group of C1 to C3 means that the lower alkyl group of C1 to C3 is linked to sulfur of the mercapto group instead of hydrogen. Examples thereof include methyl mercapto group and ethyl mercapto group.
  • R 1 in the compound of the present invention (Formula 1 or Formula 2), R 1 may be a straight or branched C1-C3 lower alkyl group, for example a methyl group, or a halogen atom, for example For example Cl, or NH 2 .
  • R 2 may be NO 2 or H, or may be a straight or branched C 1 to C 3 lower alkyl group, for example an ethyl group.
  • the pharmaceutical composition of the present invention may be administered at 0.1 to 1000 mg / kg / day, which may vary depending on the severity, age, sex, etc. of the patient.
  • Korean Patent No. 10-1338521 and J. Dermat. Sci. 67, 111-119 The chronic pruritus or atopic dermatitis induced rats disclosed in 2012 were prepared as follows.
  • Pruritus was evaluated in the same manner as in Example 4-4. The number of scratches observed during 1 hour was used as a measure of pruritus degree. Compared with the control group, it was determined that there was an improvement in pruritus when the scratching behavior was statistically significantly reduced.
  • the bars in the center of FIG. 7 represent the number of scratches accumulated between 30 minutes and 1 hour after injection in each group, and the rightmost bars represent the number of scratches accumulated between 1 hour and 1 hour and 30 minutes after injection in each group.
  • ' ⁇ 30 minutes' and '30 minutes to 1 hour' on the horizontal axis of the graph in FIG. 7 mean elapsed time after photographing start.
  • the total number of scratches accumulated in the control group for 30 minutes was 117.67 ⁇ 9.31, and the number of scratches in the compound-treated group of Formula 3 was 44.00 ⁇ 12.87. From the above results, it can be seen that the compound of Formula 3 has an effect of reducing histamine-dependent pruritus.
  • the total number of scratches accumulated in the control group for 30 minutes was 305.25 ⁇ 39.54, and the number of scratches in the compound-treated group of Formula 3 was 128.86 ⁇ 23.23. From the above results, it can be seen that the compound of Formula 3 has a significant improvement effect on histamine-independent non-histaminergic pruritus.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne un nouveau dérivé de benzoxazole à effet de prévention ou de traitement du prurit dans des troubles cutanés, et son procédé de préparation. Du fait qu'il présente une excellente activité en termes d'atténuation du prurit, le composé de dérivé de benzoxazole de l'invention peut être utilisé en tant qu'agent prophylactique, agent thérapeutique ou adjuvant thérapeutique contre un prurit dans différentes maladies de la peau, y compris la dermite atopique, le prurit histamino-dépendant et le prurit non histamino-dépendant.
PCT/KR2015/000959 2014-01-29 2015-01-29 Dérivé de benzoxazole à activité atténuant le prurit Ceased WO2015115826A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2014-0011372 2014-01-29
KR20140011372 2014-01-29

Publications (1)

Publication Number Publication Date
WO2015115826A1 true WO2015115826A1 (fr) 2015-08-06

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2015/000959 Ceased WO2015115826A1 (fr) 2014-01-29 2015-01-29 Dérivé de benzoxazole à activité atténuant le prurit

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KR (1) KR101683362B1 (fr)
WO (1) WO2015115826A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112480020A (zh) * 2020-12-11 2021-03-12 东华理工大学 一种2-取代苯并恶唑化合物

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023182735A1 (fr) * 2022-03-22 2023-09-28 주식회사 클로소사이언스 Composition de prévention ou de traitement de la dégénérescence maculaire, comprenant un composé qui induit l'expression d'un gène klotho antivieillissement

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20120139581A (ko) * 2011-06-17 2012-12-27 이화여자대학교 산학협력단 신규한 화합물, 이의 제조방법 및 이를 포함하는 골다공증 완화, 예방 또는 치료용 약학조성물
US20130096136A1 (en) * 2011-09-30 2013-04-18 Methylgene Inc. Inhibitors of Protein Tyrosine Kinase Activity

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20120139581A (ko) * 2011-06-17 2012-12-27 이화여자대학교 산학협력단 신규한 화합물, 이의 제조방법 및 이를 포함하는 골다공증 완화, 예방 또는 치료용 약학조성물
US20130096136A1 (en) * 2011-09-30 2013-04-18 Methylgene Inc. Inhibitors of Protein Tyrosine Kinase Activity

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
KIM, Y. H. ET AL.: "Facile Synthesis of 2-Substituted Aminobenzoxazole. One Pot Cyclodesulfurization of N-(2-Hydroxyphenyl)-N'-phenylthioureas with Superoxide Radical Anion", CHEMISTRY LETTERS, vol. 15, 1986, pages 1291 - 1294, XP055217931 *
PARK CHOO, H. Y. ET AL.: "Synthesis and evaluation of benzoxazole derivatives as 5-lipoxygenase inhibitors", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 18, 2010, pages 7580 - 7585, XP027415411 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112480020A (zh) * 2020-12-11 2021-03-12 东华理工大学 一种2-取代苯并恶唑化合物
CN112480020B (zh) * 2020-12-11 2023-10-10 东华理工大学 一种2-取代苯并恶唑化合物

Also Published As

Publication number Publication date
KR101683362B1 (ko) 2016-12-07
KR20150091011A (ko) 2015-08-07

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