HRP20160144T1 - Derivati etinila kao modulatori receptora metabotropskih glutamata - Google Patents
Derivati etinila kao modulatori receptora metabotropskih glutamata Download PDFInfo
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- HRP20160144T1 HRP20160144T1 HRP20160144TT HRP20160144T HRP20160144T1 HR P20160144 T1 HRP20160144 T1 HR P20160144T1 HR P20160144T T HRP20160144T T HR P20160144TT HR P20160144 T HRP20160144 T HR P20160144T HR P20160144 T1 HRP20160144 T1 HR P20160144T1
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- Prior art keywords
- phenylethynyl
- pyridin
- image
- propionamide
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- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 title claims 5
- 102000016193 Metabotropic glutamate receptors Human genes 0.000 title 1
- 108010010914 Metabotropic glutamate receptors Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
- RNUOSMNJMUZUNS-UHFFFAOYSA-N 2,2-dimethyl-n-[5-(2-phenylethynyl)pyridin-2-yl]propanamide Chemical compound C1=NC(NC(=O)C(C)(C)C)=CC=C1C#CC1=CC=CC=C1 RNUOSMNJMUZUNS-UHFFFAOYSA-N 0.000 claims 1
- XZNIYOQXRDUMCY-UHFFFAOYSA-N 2,2-dimethyl-n-[5-(2-phenylethynyl)pyrimidin-2-yl]propanamide Chemical compound C1=NC(NC(=O)C(C)(C)C)=NC=C1C#CC1=CC=CC=C1 XZNIYOQXRDUMCY-UHFFFAOYSA-N 0.000 claims 1
- HWBFRCFPMYKQRP-UHFFFAOYSA-N 2,2-dimethyl-n-[6-(2-phenylethynyl)pyridazin-3-yl]propanamide Chemical compound N1=NC(NC(=O)C(C)(C)C)=CC=C1C#CC1=CC=CC=C1 HWBFRCFPMYKQRP-UHFFFAOYSA-N 0.000 claims 1
- CZUADVARASQGCU-UHFFFAOYSA-N 2-methoxy-2-methyl-n-[5-(2-phenylethynyl)pyridin-2-yl]propanamide Chemical compound C1=NC(NC(=O)C(C)(C)OC)=CC=C1C#CC1=CC=CC=C1 CZUADVARASQGCU-UHFFFAOYSA-N 0.000 claims 1
- LWJUFPGJSOBDQK-UHFFFAOYSA-N 2-methoxy-n-[5-(2-phenylethynyl)pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)COC)=CC=C1C#CC1=CC=CC=C1 LWJUFPGJSOBDQK-UHFFFAOYSA-N 0.000 claims 1
- RHBYCEDHUUNXCL-UHFFFAOYSA-N 2-methyl-n-[5-(2-phenylethynyl)pyridin-2-yl]pentanamide Chemical compound C1=NC(NC(=O)C(C)CCC)=CC=C1C#CC1=CC=CC=C1 RHBYCEDHUUNXCL-UHFFFAOYSA-N 0.000 claims 1
- FKZRBSFGTIXFSO-UHFFFAOYSA-N 2-methylsulfanyl-n-[5-(2-phenylethynyl)pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)CSC)=CC=C1C#CC1=CC=CC=C1 FKZRBSFGTIXFSO-UHFFFAOYSA-N 0.000 claims 1
- BJWFYNYCXPMRDO-UHFFFAOYSA-N 3-methyl-n-[5-(2-phenylethynyl)pyridin-2-yl]butanamide Chemical compound C1=NC(NC(=O)CC(C)C)=CC=C1C#CC1=CC=CC=C1 BJWFYNYCXPMRDO-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 206010003805 Autism Diseases 0.000 claims 1
- 208000020706 Autistic disease Diseases 0.000 claims 1
- 208000001914 Fragile X syndrome Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 claims 1
- 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 1
- 230000003281 allosteric effect Effects 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- MRNKGHIVWGFKKT-UHFFFAOYSA-N n,2,2-trimethyl-n-[5-(2-phenylethynyl)pyrimidin-2-yl]propanamide Chemical compound C1=NC(N(C(=O)C(C)(C)C)C)=NC=C1C#CC1=CC=CC=C1 MRNKGHIVWGFKKT-UHFFFAOYSA-N 0.000 claims 1
- ICIZAOBOELJTEG-UHFFFAOYSA-N n-[5-(2-phenylethynyl)pyridin-2-yl]butanamide Chemical compound C1=NC(NC(=O)CCC)=CC=C1C#CC1=CC=CC=C1 ICIZAOBOELJTEG-UHFFFAOYSA-N 0.000 claims 1
- IEEWOHAXHXPWHL-UHFFFAOYSA-N n-[5-(2-phenylethynyl)pyridin-2-yl]pentanamide Chemical compound C1=NC(NC(=O)CCCC)=CC=C1C#CC1=CC=CC=C1 IEEWOHAXHXPWHL-UHFFFAOYSA-N 0.000 claims 1
- WSNPFRDFJAYVKA-UHFFFAOYSA-N n-[5-[2-(1h-pyrrolo[2,3-b]pyridin-2-yl)ethynyl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC=C1C#CC1=CC2=CC=CN=C2N1 WSNPFRDFJAYVKA-UHFFFAOYSA-N 0.000 claims 1
- RCHUKVKOLIFTNH-UHFFFAOYSA-N n-[5-[2-(2,5-difluorophenyl)ethynyl]pyridin-2-yl]-2-methoxy-2-methylpropanamide Chemical compound C1=NC(NC(=O)C(C)(C)OC)=CC=C1C#CC1=CC(F)=CC=C1F RCHUKVKOLIFTNH-UHFFFAOYSA-N 0.000 claims 1
- WLTKTNOYOWUNAP-UHFFFAOYSA-N n-[5-[2-(3-fluorophenyl)ethynyl]pyridin-2-yl]-2,2-dimethylpropanamide Chemical compound C1=NC(NC(=O)C(C)(C)C)=CC=C1C#CC1=CC=CC(F)=C1 WLTKTNOYOWUNAP-UHFFFAOYSA-N 0.000 claims 1
- NYMXUGNIKMSYSK-UHFFFAOYSA-N n-[5-[2-(3-fluorophenyl)ethynyl]pyridin-2-yl]-2-methoxy-2-methylpropanamide Chemical compound C1=NC(NC(=O)C(C)(C)OC)=CC=C1C#CC1=CC=CC(F)=C1 NYMXUGNIKMSYSK-UHFFFAOYSA-N 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 125000003566 oxetanyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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- A61K31/50—Pyridazines; Hydrogenated pyridazines
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- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
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Claims (10)
1. Derivati etinila, naznačeni time, da imaju formulu IA, IB i ID:
[image]
gdje
R1 fenil ili heteroaril, koji su opcijski supstituirani s halogenom, C1-4-alkilom ili
C1-4-alkoksi;
R2 je vodik ili C1-4-alkil;
R' j. vodik, C1-4-alkil, C1-4-alkoksi, CF3 ili S-C1-4-alkil;
R3/R3' su međusobno neovisno vodik, C1-4-alkil ili C1-4-alkoksi, ili
R3 i R3' zajedno tvore C3-5-cikloalkil-prsten, tetrahidrofuran-prsten ili oksetan-prsten;
ili njihova farmaceutski prikladna kiselinska adicijska sol, racemidna smjesa ili njihov odgovarajući enantiomer i/ili njihov optidki izomer i/ili stereoizomer, s izuzetkom spoja N-(5-((1H-pirolo[2,3-B]piridin-2-il) etinil) piridin-2-il)acetamida.
2. Derivati etinila formule IA prema zahtjevu 1, naznačeni time, da su to sljedeći spojevi:
2,2-dimetil-N-(5-feniletinil-piridin-2-il)-propionamid,
N-(5-feniletinil-piridin-2-il)-butiramid,
pentanoinska kiselina-(5-feniletinil-piridin-2-il)-amid,
3-metil-N-(5-feniletinil-piridin-2-il)-butiramid,
(RS)-2-metil-pentanoinska kiselina-(5-feniletinil-piridin-2-il)-amid,
2-metilsulfanil-N-(5-feniletinil-piridin-2-il)-acetamid,
2-metoksi-N-(5-feniletinil-piridin-2-il)-acetamid,
N-[5-(3-fluoro-feniletinil)-piridin-2-il]-2,2-dimetil-propionamid,
2-metoksi-2-metil-N-(5-feniletinil-piridin-2-il)-propionamid,
N-[5-(3-fluoro-feniletinil)-piridin-2-il]-2-metoksi-2-metil-propionamid,
N-[5-(2,5-difluoro-feniletinil)-piridin-2-il]-2-metoksi-2-metil-propionamid ili
N-[5-(3-kloro-feniletinil)-piridin-2-il)-3,3,3-trifluoro-2,2-dimetil-propionamid.
3. Derivati etinila formule IB prema zahtjevu 1, naznačeni time, da su to sljedeći spojevi:
2,2-dimetil-N-(5-feniletinil-pirimidin-2-il)-propionamid ili 2,2,N-trimetil-N-(5-feniletinil-pirimidin-2-il)-propionamid.
4. Derivati etinila formule ID prema zahtjevu 1, naznačeni time, da su to sljedeći spojevi:
2,2-dimetil-N-(6-feniletinil-piridazin-3-il)-propionamid ili
N-[6-(3-kloro-feniletinil)-piridazin-3-il)-2,2-dimetil-propionamid.
5. Postupak proizvodnje spoja formule I, koji je opisan u bilo kojem od zahtjeva 1 do 4, naznačen time, da on obuhvaća sljedeću varijantu:
a) reakcija spoja formule:
[image]
s prikladnim spojem formule:
[image]
za dobivanje spoja sljedećih formula:
[image]
[image]
pri čemu su supstituenti opisani u zahtjevu 1, ili po želji, pretvaranje spojeva koji su dobiveni u farmaceutski prikladne kiselinske adicijske soli, ili
b) reakcija spoja formule:
[image]
s prikladnim spojem formule:
[image]
za dobivanje spoja sljedećih formula:
[image]
[image]
pri čemu su supstituenti odabrani u zahtjevu 1, ili po želji, pretvaranje dobivenih spojeva u farmaceutski prikladne kiselinske adicijske soli, ili
c) reakcija spoja sljedećih formula:
[image]
s prikladnim spojem formule:
[image]
za dobivanje spoja sljedećih formula:
[image]
[image]
ili
[image]
pri čemu su supstituenti odabrani u zahtjevu 1, ili po želji, pretvaranje dobivenih spojeva u farmaceutski prikladne kiselinske adicijske soli"
6. Spoj prema bilo kojem od zahtjeva 1 do 4, naznačen time, da se on upotrebljava kao terapeutski djelotvorna tvar.
7. Farmaceutski sastav, naznačen time, da on obuhvaća spojeve prema bilo kojem od zahtjeva 1 do 4, kao i njihovu farmaceutski prikladnu sol.
8. Spoj prema bilo kojem od zahtjeva I do 4, naznačen time, da se primjenjuje u obliku mješavina enantiomera, diastereomera ili u čistom enantiomernom obliku, kao i njegova farmaceutski prikladna sol, pri čemu se tada upotrebljava kao lijek.
9. Uporaba spoja prema bilo kojem od zahtjeva 1 do 4, kao i njegove farmaceutski prikladne soli, naznačena time, da je za proizvodnju lijeka za liječenje ili prevenciju bolesti koje se odnose na alosterne modulatore od receptora mGluR5.
10. Spoj prema bilo kojem od zahtjeva 1 do 4, naznačen time, da se upotrebljava za liječenje ili prevenciju shizofrenije, kognitivnih bolesti, sindroma fragilnog X ili autizma.
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EP11184257 | 2011-10-07 | ||
PCT/EP2012/069605 WO2013050460A1 (en) | 2011-10-07 | 2012-10-04 | Ethynyl derivatives as metabotropic glutamate receptor modulators |
EP12772100.9A EP2763969B1 (en) | 2011-10-07 | 2012-10-04 | Ethynyl derivatives as metabotropic glutamate receptor modulators |
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CN (1) | CN103857658B (hr) |
AR (1) | AR088765A1 (hr) |
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CA (1) | CA2847096A1 (hr) |
CL (1) | CL2014000818A1 (hr) |
CO (1) | CO6900142A2 (hr) |
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HU (1) | HUE026626T2 (hr) |
IL (1) | IL231439A (hr) |
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WO (1) | WO2013050460A1 (hr) |
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UA113223C2 (xx) * | 2012-08-13 | 2016-12-26 | Арилетинілпіримідини | |
MY171517A (en) * | 2012-10-18 | 2019-10-16 | Hoffmann La Roche | Ethynyl derivatives as modulators of mglur5 receptor activity |
JP6603334B2 (ja) | 2015-06-03 | 2019-11-06 | エフ.ホフマン−ラ ロシュ アーゲー | エチニル誘導体 |
PE20180356A1 (es) | 2015-07-15 | 2018-02-21 | Hoffmann La Roche | Derivados de etinilo como moduladores del receptor metabotropico del glutamato |
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EP1303495B1 (en) * | 2000-07-24 | 2010-05-26 | Krenitsky Pharmaceuticals, Inc. | Substituted 5-alkynyl pyrimidines having neurotrophic activity |
GB0325956D0 (en) | 2003-11-06 | 2003-12-10 | Addex Pharmaceuticals Sa | Novel compounds |
US7776869B2 (en) | 2004-10-18 | 2010-08-17 | Amgen Inc. | Heteroaryl-substituted alkyne compounds and method of use |
WO2006048771A1 (en) | 2004-11-04 | 2006-05-11 | Addex Pharmaceuticals Sa | Novel tetrazole derivatives as positive allosteric modulators of metabotropic glutamate receptors |
AU2006226669B2 (en) * | 2005-03-23 | 2011-12-08 | F. Hoffmann-La Roche Ag | Acetylenyl-pyrazolo-pvrimidine derivatives as mGluR2 antagonists |
GB0510139D0 (en) | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B1 |
MX2009013169A (es) | 2007-06-03 | 2010-04-30 | Univ Vanderbilt | Moduladores alostericos positivos del mglur5 benzamida y metodos de elaboracion y uso de los mismos. |
US8853392B2 (en) | 2007-06-03 | 2014-10-07 | Vanderbilt University | Benzamide mGluR5 positive allosteric modulators and methods of making and using same |
EP2323992B1 (en) | 2008-07-29 | 2016-07-20 | Boehringer Ingelheim International GmbH | 5-alkynyl-pyrimidines |
US8389536B2 (en) * | 2009-10-27 | 2013-03-05 | Hoffmann-La Roche Inc. | Positive allosteric modulators (PAM) |
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