HUE025411T2 - Azetidinszármazékok - Google Patents
Azetidinszármazékok Download PDFInfo
- Publication number
- HUE025411T2 HUE025411T2 HUE09716712A HUE09716712A HUE025411T2 HU E025411 T2 HUE025411 T2 HU E025411T2 HU E09716712 A HUE09716712 A HU E09716712A HU E09716712 A HUE09716712 A HU E09716712A HU E025411 T2 HUE025411 T2 HU E025411T2
- Authority
- HU
- Hungary
- Prior art keywords
- phenyl
- yloxy
- azetidine
- pyridin
- optionally substituted
- Prior art date
Links
- 150000001539 azetidines Chemical class 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 127
- -1 di-propyl Chemical group 0.000 claims description 79
- 230000000694 effects Effects 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- 208000002193 Pain Diseases 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 16
- 230000036407 pain Effects 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000006413 ring segment Chemical group 0.000 claims description 12
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- 206010061218 Inflammation Diseases 0.000 claims description 10
- 230000004054 inflammatory process Effects 0.000 claims description 10
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 10
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 10
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- 230000036506 anxiety Effects 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 206010047700 Vomiting Diseases 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
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- 206010015037 epilepsy Diseases 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 5
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 4
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 230000004770 neurodegeneration Effects 0.000 claims description 3
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- 230000000926 neurological effect Effects 0.000 claims description 3
- 125000005551 pyridylene group Chemical group 0.000 claims description 3
- 208000020685 sleep-wake disease Diseases 0.000 claims description 3
- 230000003612 virological effect Effects 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
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- 206010021639 Incontinence Diseases 0.000 claims description 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
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- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 206010010071 Coma Diseases 0.000 claims 1
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- 101000937693 Homo sapiens Fatty acid 2-hydroxylase Proteins 0.000 claims 1
- 101000918494 Homo sapiens Fatty-acid amide hydrolase 1 Proteins 0.000 claims 1
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- 208000025966 Neurological disease Diseases 0.000 claims 1
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- KVVMXWRFYAGASO-UHFFFAOYSA-N azetidine-1-carboxylic acid Chemical compound OC(=O)N1CCC1 KVVMXWRFYAGASO-UHFFFAOYSA-N 0.000 claims 1
- 208000002173 dizziness Diseases 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- 210000000987 immune system Anatomy 0.000 claims 1
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- TVPRCLHSULCNLV-UHFFFAOYSA-N pyridazin-3-one Chemical compound O=C1C=CC=N[N]1 TVPRCLHSULCNLV-UHFFFAOYSA-N 0.000 claims 1
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
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Claims (8)
- Szabadalmi igénypontok 1 „ Egy (!) képletű vegyűiet, vagy egy gyógyszerészetileg elfogadható sója:ω ahol a képletben Ar jelentése adott esetben szubsztituált feni- vagy adott esetben szubsztituált δ vagy S gyűrű atomot tartalmazó monodklusos heteroanlcsoport; Ar2 jelentése adott esetben szubsztituált fenil-, adott esetben szubsztituált 5 vagy δ gyűrű atomot tartalmazó monociklusos heteroahlesoport vagy adod esetben szubsztituált kondenzált, mindegyik kondenzált gyűrűben 5 vagy 6 gyűrű atomot tartalmazó foicíklusos heteroanlcsopori; és Ar3 jelentése az alábbiakból álló csoportból választott kétértékű csoport: adott esetben szubsztituált ferdén- és adott esetben szubsztituált δ vagy δ gyűrű atomot tartalmazó monodklusos heteroarlléncsoportok; és ahol az Ar1, Ar2 és Ar3 csoportokban adott esetben található bármely szubsztituens jelentése egymástól függetlenül klór, fluor, bróm, dkiopropil, metil, mono-, dí- vagy tri-metll, trifluor-metll, difluor-metil, monofluor-metil, metoxi, etoxi. propoxi, buíoxi, pentoxí, 2-metoxl~eioxi: 2-benzil-oxi-etoxi, 2-hldoxl-etoxl, mono-, dl- vagy trl-fluor-metoxl, ciano, bidoxil; -CO2R1 és -SO2R1 ahol Rí jelentése hidrogén, metil vagy etil; tetrazoüi; -NR2R3, -CH2MR2R3 és -0^O):NR2R3 ahol R2 és R3 jelentése egymástól függetlenül hidrogén, metil vagy etil.
- 2. Az 1. igénypont szerinti vegyűiet ahol Ar1 jelentése adott esetben szubsztituált fenilcsoport. 3» Az 1. vagy 2. igénypont szerinti vegyűiet, ahol Ar2 jelentése fenil, piridil, pirimidinil, piraziní! vagy plrídazlnilcsoport, amelyek közül bármelyik csoport adott esetben szubsztituált
- 4. Az 1 vagy 2. igénypont szerinti vegyűiet, ahol Ar2 jelentése 3-piridI, pirimkJ!n-4~H, pirazin-2-8 vagy piridazin-3-i, amelyek közül bármelyik csoport adott esetben szubsztituált,
- 5, Az előző Igénypontok bármelyike szennti vegyület ahol Ár3 jelentése adott esetben szubsztííuált kétértékű lenién- vagy piridiléncsopori
- 6. Az 5. Igénypont szerinti vegyület, ahol Ár3 jelentése adott esetben; szubsztííuált kétértékű 1 ,4-fenlíén- vagy azalábbi képlete 2,5-pindiIéncsoporí: aho! az egy csillaggal letölt kötés Ar csoporthoz kapcsolódik és a két csillaggal jeléit csoport oxigénhez kapcsolódik. ?> Az 1. igénypont szerinti vegyülel ahol: Ar2 jelentése 3-piridi, pirimtötn-édl, pirazln-2-lí vagy pridazin~3»il: Ar jelentése adott esetben szubsztííuált kétértékű 1,4-fenílén- vagy az alábbi képié-tű 2,5-pirldinlíéncsopönahol az egy csillaggal jelölt kötés Ar1 csoporthoz kapcsolódik és a két csillaggal jelölt Ar1 jelentése adott esetben szybsztltuált fenllcsopork 8. A 7. Igénypont szerint vegyülel, ahol Ar1 jelentése feni, 2-fluor~fenil, 3-(2--metoxi-etoxi)~fenlL vagy 2~meioxi-5~(2-rneioxi~etoxi)-fenii., 8* A 7. vagy 8. igénypont szerinti vegyület, ahol Ar2 jelentése piriéazín~3-ií.
- 10. Az 1. igénypont szerinti alábbi vegyület: í3~(8ifenli-4-ii-Dxi)-azetidin~1-karbonsavHplridin-3-ll“amidjt [3-{5~FenIS-píndín-2~il-oxi}-azetidin~1~karbonsavHpirídazín~3-ií-8míd], {3-[5-(2-fv1etoxí~fenII}-piridin-2-iI~oxij-azetidín~1-karbonsav}-[pirídazin-3-il-amin}, {3-j5~(2-Fiüor"fens])-'piridin''2-il-'OXÍj-azetidin-'1-karbonsav}-íp!ndazin-3-il~arnidj) {S-IS-^-jS-yetoxl-etoxiHenilj-piridín^-iboxIVazetidin-l-karbonsavj-jpIndin-S-Ii-amidj, {S-jS-jS-CS-yetoxi-etoxiHenílj-pindín^-ii-oxij-azetídln-l-karbonsavHpiridazín-S-ll--amid], (3-{S-13-{2-Benzíi-oxi-etoxi)-feniIj-piridín-2-Ii~oxi}-a2et)din-1-karbonsav}-rplridazin-3-iI~ -amid], f3~ͧ-|2~:FIuor-fenilj-píndIn-2-il-oxi]-azetÍdÍn~1-ka:rbonsav}~[pirazín~2-il'arn3d| t3-[5-{2,6-Dif!üor-fenil}-píridin~2-i!-oxn~azetidirs~1-karbonsav}-ípirídazin-3-il-amíd]:< {345~|2-Kiôr“5~{2~metQxî'-eioxâ)4enil|~pMdin~2~îl-ox|~azetid:i:n-1-karbonsavHPW^az^n”3~ -íj-amid], 11« Gyógyszerkészítmény, amely az előzd igénypontok bármelyike szerinti vegyöletet egy vagy több gyógyszerészetíieg elfogadható vivőanyaggal és/vagy kötőanyaggal együtt tartalmazza,
- 12. Az 1-íÖ. Igénypontok bármelyike szedeti vegyuiet a gyógyításban: történő alkalmazásra, 13« Az 1-10. igénypontok bármelyike szerinti vegyuiet a FAAH aktivitás gátlására Javuló betegségek vagy orvosi állapotok kezelésére, amelyeket az alábbiak közűi választunk: akut vagy krónikus fájdalom, szédülés, hányás, hányinger, evési rendellenességek, neurológiai és pszichiátriai kórok, akut vagy krónikus neurodegenerativ betegségek, epilepszia, alvási rendellenességek, kardiovaszkuláris betegségek, vese ischémie, rákos betegségek, immunrendszer! rendellenességek, allergiás betegségek, parazita, vírusos vagy bakteriális fertőző betegségek, gyulladásos betegségek, csontritkulás. szemészeti panaszok, tüdő panaszok, gasztrointesztináfis betegségek, giau-kómával összefüggő magas vérnyomás és vizeiét inkontínencia.
- 14. Az 1-10. igénypontok bármelyike szerinti vegyületek szorongás, depresz-szió, fájdalom, gyulladás, bőrviszketés, alvási rendellenesség vagy mozgási rendellenesség kezelésére.
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GBGB0804006.5A GB0804006D0 (en) | 2008-03-04 | 2008-03-04 | Azetidine derivatives |
GBGB0821694.7A GB0821694D0 (en) | 2008-11-27 | 2008-11-27 | Azetidine derivatives |
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AU2009220974B2 (en) | 2008-03-04 | 2013-10-24 | Vernalis (R&D) Ltd. | Azetidine derivatives |
US20130150346A1 (en) | 2010-01-08 | 2013-06-13 | Quest Ventures Ltd. | Use of FAAH Inhibitors for Treating Parkinson's Disease and Restless Legs Syndrome |
WO2011123719A2 (en) | 2010-03-31 | 2011-10-06 | Ironwood Pharmaceuticals, Inc. | Use of faah inhibitors for treating abdominal, visceral and pelvic pain |
KR101273566B1 (ko) * | 2011-09-05 | 2013-06-11 | 한국과학기술연구원 | 신규한 아제티딘 유도체 및 이를 함유하는 항우울제 조성물 |
AU2013202982C1 (en) * | 2012-01-06 | 2017-01-05 | Novartis Ag | Heterocyclic compounds and methods for their use |
US10570146B2 (en) * | 2014-07-25 | 2020-02-25 | Northeastern University | Urea/carbamates FAAH MAGL or dual FAAH/MAGL inhibitors and uses thereof |
JOP20190072A1 (ar) * | 2016-10-13 | 2019-04-07 | Glaxosmithkline Ip Dev Ltd | مشتقات 1، 3 سيكلوبوتان ثنائي الاستبدال أو آزيتيدين كمثبطات للإنزيم المخلق للبروستاجلاندين d المكون للدم |
KR20200003102A (ko) * | 2017-06-02 | 2020-01-08 | 후지필름 도야마 케미컬 가부시키가이샤 | 아밀로이드 β 단백질량 감소제 |
BR112019024851A2 (pt) | 2017-06-02 | 2020-06-09 | Fujifilm Toyama Chemical Co Ltd | agente para evitar ou tratar atrofia cerebral |
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EP4243811A1 (en) * | 2020-07-21 | 2023-09-20 | Neuritek Ltd. | Uses of fatty acid amide hydrolase inhibitors in treatment of trauma related psychiatric disorders |
CN112374984A (zh) * | 2020-11-06 | 2021-02-19 | 苏州求索生物科技有限公司 | 一种2-溴-4-羟基苯甲醚的制备工艺 |
US11141404B1 (en) | 2020-11-18 | 2021-10-12 | Anebulo Pharmaceuticals, Inc. | Formulations and methods for treating acute cannabinoid overdose |
US11795146B2 (en) | 2021-10-11 | 2023-10-24 | Anebulo Pharmaceuticals, Inc. | Crystalline forms of a cannabinoid receptor type 1 (CB1) modulator and methods of use and preparation thereof |
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US5183902A (en) * | 1985-02-28 | 1993-02-02 | A. H. Robins Company, Incorporated | Method of treating muscular tension, muscle spasticity and anxiety with 3-aryloxy and 3-arylthioazetidinecarboxamides |
US6335445B1 (en) * | 1997-03-24 | 2002-01-01 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) | Derivatives of 2-(iminomethyl)amino-phenyl, their preparation, their use as medicaments and the pharmaceutical compositions containing them |
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