TR201922091A2 - P38 mapk i̇nhi̇bi̇törü ve anti̇kanser etki̇nli̇ğe sahi̇p üre türevleri̇ni̇n sentezi̇ - Google Patents
P38 mapk i̇nhi̇bi̇törü ve anti̇kanser etki̇nli̇ğe sahi̇p üre türevleri̇ni̇n sentezi̇Info
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- TR201922091A2 TR201922091A2 TR2019/22091A TR201922091A TR201922091A2 TR 201922091 A2 TR201922091 A2 TR 201922091A2 TR 2019/22091 A TR2019/22091 A TR 2019/22091A TR 201922091 A TR201922091 A TR 201922091A TR 201922091 A2 TR201922091 A2 TR 201922091A2
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 10
- 230000001093 anti-cancer Effects 0.000 title description 4
- 230000015572 biosynthetic process Effects 0.000 title description 4
- 238000003786 synthesis reaction Methods 0.000 title description 4
- 229940126560 MAPK inhibitor Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims abstract description 4
- 239000002246 antineoplastic agent Substances 0.000 claims abstract description 4
- 210000000481 breast Anatomy 0.000 claims abstract description 4
- 201000005202 lung cancer Diseases 0.000 claims abstract description 4
- 208000020816 lung neoplasm Diseases 0.000 claims abstract description 4
- 206010006187 Breast cancer Diseases 0.000 claims abstract description 3
- 208000026310 Breast neoplasm Diseases 0.000 claims abstract description 3
- 206010014733 Endometrial cancer Diseases 0.000 claims abstract description 3
- 206010014759 Endometrial neoplasm Diseases 0.000 claims abstract description 3
- 229940044683 chemotherapy drug Drugs 0.000 claims abstract description 3
- 210000004072 lung Anatomy 0.000 claims abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 3
- -1 3,5-bistrifluoromethylphenyl Chemical group 0.000 claims description 11
- 206010028980 Neoplasm Diseases 0.000 claims description 11
- 201000011510 cancer Diseases 0.000 claims description 11
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 229940125532 enzyme inhibitor Drugs 0.000 claims 1
- 239000002532 enzyme inhibitor Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 abstract description 4
- 108090000790 Enzymes Proteins 0.000 abstract description 4
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 description 13
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 description 13
- 230000001472 cytotoxic effect Effects 0.000 description 7
- 231100000433 cytotoxic Toxicity 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 239000004202 carbamide Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 229940043355 kinase inhibitor Drugs 0.000 description 5
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 4
- 102000043136 MAP kinase family Human genes 0.000 description 3
- 108091054455 MAP kinase family Proteins 0.000 description 3
- 229940000406 drug candidate Drugs 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 2
- 239000002547 new drug Substances 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- NDNNMJBUIRIZNP-UHFFFAOYSA-N 1,3-thiazole;thiophene Chemical group C=1C=CSC=1.C1=CSC=N1 NDNNMJBUIRIZNP-UHFFFAOYSA-N 0.000 description 1
- PBAVKKUMNXUDMV-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-3-(4-thiophen-2-yl-1,3-thiazol-2-yl)urea Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(NC(=O)NC=2SC=C(N=2)C=2SC=CC=2)=C1 PBAVKKUMNXUDMV-UHFFFAOYSA-N 0.000 description 1
- SZCBDIVMCGFVPW-UHFFFAOYSA-N 1-[4-(aminomethyl)-2,6-di(propan-2-yl)phenyl]-3-[1-butyl-4-(3-methoxyphenyl)-2-oxo-1,8-naphthyridin-3-yl]urea;hydrochloride Chemical compound Cl.CC(C)C=1C=C(CN)C=C(C(C)C)C=1NC(=O)NC=1C(=O)N(CCCC)C2=NC=CC=C2C=1C1=CC=CC(OC)=C1 SZCBDIVMCGFVPW-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 208000021722 neuropathic pain Diseases 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 208000028169 periodontal disease Diseases 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Buluş, p38MAPK enzimini inhibe ederek meme, akciğer ve endometriyum kanserinin tedavisi için kullanılabilecek bileşikler, bu bileşikleri içeren farmasötik kompozisyonlar ve söz konusu kompozisyonların kemoterapötik ilaç adayı olarak kullanımı ile ilgilidir.
Description
TARIFNAME P38 MAPK INHIBITÖRÜ VE ANTIKANSER ETKINLIGE SAHIP ÜRE TÜREVLERININ SENTEZI Bulusun Ilgili Oldugu Teknik Alan Bulus, meme, akciger ve endometriyum kanserinin tedavisi için etkili ve yeni bir kemoterapötik ilaç adayi olan ve yüksek anti-kanser aktiviteye sahip ilaç adayinin sentezlenmesi ile ilgilidir Bulusla Ilgili Teknigin Bilinen Durumu (Önceki Teknik) Mitogen ile aktive olan protein kinaz (MAPK) enzimleri istisnai düzenleme özelligine sahip olup, kanser ve diger hastaliklarin tedavisinde önemli bir katkiya sahiptirler. p38 mitogen aktive olan protein kinaz (p38MAPK) enziminin sinyal iletim yollarinda, agri ve inflammasyonda önemli göreve sahip oldugu bilinmektedir. Son yillarda yapilan çalismalarda ise p38MAPK enziminin dört farkli analogundan biri olan p38MAPKOL inhibitörlerinin kanser tedavisinde, nöropathik agrilarda ve periodental hastaliklarda önemli tedavi edici özellikleri ortaya konulmustur. Sonuç olarak antiinflamatuvar ve anti kanser ilaç olma potansiyeline sahip p38MAPKOL inhibitörü gelistirme çalismalari çok büyük ilgi çekmektedir. Teknigin bilinen durumunda p38MAPK inhibitörü aktivitesi gösteren çok sayida küçük moleküller sinifinda yer alan bilesiklerin sentezi gerçeklestirilmis olup, bunlar ile ilgili çok sayida patent bulunmaktadir. kinaz inhibitörü olarak sentezlenmistir. kinaz inhibitörü olarak sentezlenmistir. halkali heterosiklik bilesikler p38 kinaz inhibitörü olarak sentezlenmistir. yapisi içeren bilesikler p38 kinaz inhibitörü olarak sentezlenmistir. kinaz inhibitörü olarak sentezlenmistir. Kisacasi üre yapisi içeren bilesikler, p38MAPKOt enzim inhibisyonu gösterme potansiyeline sahip bilesikler arasinda yer almaktadir. Kanser tedavisi için çesitli ilaçlar klinikte kullanilmaktadir. Ancak, kanser hücrelerinin de ilaçlara karsi direnç gelistirmesi yeni ilaç arayislarina her zaman ihtiyaç dogurmaktadir. Yeni ilaç adayi olarak sentez edilen ve tasarlanan yeni moleküller daha önce gerçeklestirilen çalismalar isiginda gerçeklestirilmekte olsa da kimyasal yapilari farkli olmasi nedeniyle daha önceki ilaçlarda yasanan direnç gelisimi gibi dezavantajlari giderecek alternatifler farkli ilaçlar olarak tasarlanmakta ve sentez edilmektedir. Bulusun Kisa Açiklamasi ve Amaçlari Bulus ile p38MAPK enzimini inhibe eden üre yapisi içeren kanser tedavisinde etkili bilesikler sentezlenmistir. Bulus ile sentezlenen 18a, 19a, 23a kodlu bilesikler sitotoksik özellikte olup p38MAPK yolagini da inhibe etmektedir. Ayrica 23a kodlu bilesigin, p38MAPK inhibitörü olarak bilinen BIRB-7967dan daha etkili bulunmustur. Bulus ile sentezlenen 18a, 19a ve 23a bilesiklerinin kanser tedavisinde etkili olduklari tespit edilmistir. Bulusun Ayrintili Açiklamasi Bulus ile kanser hastaliginin tedavisinde kullanilabilecek üre yapisi içeren yeni bilesikler sentezlenmistir. Bu kapsamda tiyofen-tiyazol yapisi içeren 23 tane farkli üre (la-23a) türevi sentezlenmistir. l3a: R: 2-methoxyphenyl l4a: R: 2-4-dimethoxyphenyl 15a: R: 3,4-dimethoxyphenyl 17a: R: 4-trifluoromethylphenyl 18a: R: 3,5-bistrifluoromethylphenyl 19a: R: 3-chloro-4-fluorophenyl 20a: R: 4-trifluoromethoxyphenyl la: R: phenyl 2a: R: 4-fluorophenyl 3a: R: 3-fluorophenyl 4a: R: 4-chlorophenyl 5a: R: 4-bromophenyl 6a: R: 4-nitrophenyl 7a: R: 4-cyanophenyl Sa: R: 3-cyanophenyl . . 9a: R: 4-methylphenyl 21a: R: 2-pyridine 10a: R: 3-methylphenyl 2221: R: l-naphtyl l la: R: 3-trifluoromethyl- 23 a: R: 4-tertbutylphenyl 4-chlorophenyl 12a: R: 4-methoxyphenyl Bulus ile p38 MAPK inhibitörü etkinlik üzerinden kanserde etkili olabilecek üre türevi yeni ilaç moleküllerinin sentezlenmesi amaçlanmistir. Bu amaçla sentezlenen 23 farkli üre türevi bilesikten üç tanesi denenen hücre hatlarinda sitotoksik bulunmustur. Sentezlenen yeni ürünler için kullanilan yöntem bilinen sentez yöntemleri olmakla birlikte, sentez sonucunda elde edilen bilesikler yeni bilesiklerdir. Sentezlenen ürünler orijinal yeni ürünler olmakla birlikte, sentezlenen bu yeni moleküllerin sitotoksik etkilerinin degerlendirilmesinde ilk kez gerçek zamanli hücre analizörü kullanilmistir. Gerçek zamanli hücre analizörü (xCelligence) sistemi hücre çogalmasini gerçek zamanli olarak izleyen güvenilirligi en yüksek sitotoksisite yöntemlerinden birisidir ve bulusta sentezlenen yeni üre türevi ilaç adaylarinin sitotoksik etkileri bu yöntem ile degerlendirilmistir. Ayrica bulus moleküller yeni moleküller olmalari nedeniyle p38MAPK enzimi üzerinden etki edip etmedigi de ilk kez bu çalisma ile gösterilmistir. 18a, 19a ve 23a maddelerinin antikanser etkinlikleri degerlendirildiginde; 18a maddesi MDA-MB-23l meme ve A549 akciger kanser hücre hatlarinda sitotoksik bulunmustur ve p38MAPK7i da en güçlü inhibe eden bilesiklerden birisi oldugu gösterilmistir. 18a bilesigi etki mekanizmasi olarak p38MAPK yolagi üzerinden sitotoksik etki gösteriyor olabilir kanaatine varilmistir. 19a maddesi yine A549 ve RL95-2 hücrelerinde sitotoksik bulunmus ve ayni zamanda bu hücrelerde p38MAPK7i inhibe ettigi gösterilmistir. 23a ise tüm hücrelerde sitostatik etki göstermistir ve MDA-MB-23l ve RL95-27de p38MAPK inhibisyonu yaptigi görülmüstür. NMR, IR ve HRMS ile karakterize edilmistir. S \S\`I}\l E CF3 N-[(2-tiyenil)-2-tiyazolil]-N'-(3,5-bistriflorometilfenil)üre N-[(2-tiyenil)-2-tiyazolil]-N'-(3 -klor0-4-Il0r0fenil)üre N-[(2-tiyenil)-2-tiyazolil]-N'-(4-tert-butilfenil)üre TR TR
Claims (7)
1. Formül (I)7e sahip olan bilesik veya bunlarin farmasötik açidan kabul edilebilir tuzu ve/Veya solvati. S Formül (1) la: R: phenyl l3a: R: 2-meth0xyphenyl 2a: R: 4-flu0r0phenyl l4a: R: 2-4-dimeth0xyphenyl 3a: R: 3-flu0r0phenyl 15a: R: 3,4-dimeth0xyphenyl 5a: R: 4-br0m0phenyl l7a: R: 4-triflu0r0methylphenyl 6a: R: 4-nitr0phenyl 18a: R: 3,5-bistrifluoromethylphenyl Sa: R: 3-cyan0phenyl 20a: R: 4-triflu0r0meth0xyphenyl 9a: R: 4-methylphenyl 213: R: 2-pyr1dine lOa: R: 3-methylphenyl 223: R: l-naphtyl l la: R: 3-triflu0r0methyl- 23 a: R: 4-tertbutylphenyl 4-ch10r0phenyl 12a: R: 4-meth0xyphenyl
2. Istem l7e uygun bilesik olup özelligi; N-[(2-tiyenil)-2-tiyazolil]-N'-(3,5-bistriIlorometilfenil)üre 18aCl N-[(2-tiyenil)-2-tiyazolil]-N'-(3 -kloro-4-florofenil)üre N-[(2-tiyenil)-2-tiyazolil]-N'-(4-tert-butilfenil)üre gruplarindan seçilmesidir.
3. Istem 2 “e uygun bilesik olup özelligi; p38MAPK0L enzim inhibitörü olmasidir
4. Istem 3 “e uygun bilesik olup özelligi; kanser tedavisinde kullanilmasidir.
5. Istem 47e uygun bilesik olup özelligi; hedef kanserin meme, akciger ve endometriyum kanseri olmasidir. 15
6. Istem l7e uygun bilesik içeren farmasötik kompozisyon.
7. Istem 6 “e uygun farmasötik kompozisyonun kanser tedavisinde kullanilacak kemoterapötik ilacin hazirlanmasinda kullanilmasi.10
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TR2019/22091A TR201922091A2 (tr) | 2019-12-27 | 2019-12-27 | P38 mapk i̇nhi̇bi̇törü ve anti̇kanser etki̇nli̇ğe sahi̇p üre türevleri̇ni̇n sentezi̇ |
| PCT/TR2020/051274 WO2021133319A1 (en) | 2019-12-27 | 2020-12-11 | Synthesis of urea derivatives which have p38 mapk inhibition and anticancer efficacy |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TR2019/22091A TR201922091A2 (tr) | 2019-12-27 | 2019-12-27 | P38 mapk i̇nhi̇bi̇törü ve anti̇kanser etki̇nli̇ğe sahi̇p üre türevleri̇ni̇n sentezi̇ |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TR201922091A2 true TR201922091A2 (tr) | 2021-07-26 |
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| Application Number | Title | Priority Date | Filing Date |
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| TR2019/22091A TR201922091A2 (tr) | 2019-12-27 | 2019-12-27 | P38 mapk i̇nhi̇bi̇törü ve anti̇kanser etki̇nli̇ğe sahi̇p üre türevleri̇ni̇n sentezi̇ |
Country Status (2)
| Country | Link |
|---|---|
| TR (1) | TR201922091A2 (tr) |
| WO (1) | WO2021133319A1 (tr) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9926588B2 (en) * | 2007-06-04 | 2018-03-27 | The Trustees Of The University Of Pennsylvania | Method for testing and screening P38 MAP kinase modifiers |
| WO2015153959A2 (en) * | 2014-04-04 | 2015-10-08 | The Regents Of The University Of Michigan | Small molecule inhibitors of mcl-1 and uses thereof |
-
2019
- 2019-12-27 TR TR2019/22091A patent/TR201922091A2/tr unknown
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2020
- 2020-12-11 WO PCT/TR2020/051274 patent/WO2021133319A1/en active Application Filing
Also Published As
| Publication number | Publication date |
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| WO2021133319A1 (en) | 2021-07-01 |
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