ME02811B - Amino-supstituisani imidazo[1, 2-a]piridinkarboksamidi i njihova primena - Google Patents
Amino-supstituisani imidazo[1, 2-a]piridinkarboksamidi i njihova primenaInfo
- Publication number
- ME02811B ME02811B MEP-2017-164A MEP2017164A ME02811B ME 02811 B ME02811 B ME 02811B ME P2017164 A MEP2017164 A ME P2017164A ME 02811 B ME02811 B ME 02811B
- Authority
- ME
- Montenegro
- Prior art keywords
- amino
- carboxamide
- oxy
- pyridine
- ent
- Prior art date
Links
- -1 AMINO-SUBSTITUTED IMIDAZO [1,2-A] PYRIDINE Chemical class 0.000 title claims 5
- 150000001875 compounds Chemical class 0.000 claims 26
- 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 4
- ZMBYQTGAXZOMOO-UHFFFAOYSA-N imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=CC=CN2C(C(=O)N)=CN=C21 ZMBYQTGAXZOMOO-UHFFFAOYSA-N 0.000 claims 4
- 239000012442 inert solvent Substances 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 238000011321 prophylaxis Methods 0.000 claims 3
- 238000011282 treatment Methods 0.000 claims 3
- 206010002383 Angina Pectoris Diseases 0.000 claims 2
- 206010003210 Arteriosclerosis Diseases 0.000 claims 2
- 208000010496 Heart Arrest Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 102220632799 Immunoglobulin heavy variable 1-69_R11A_mutation Human genes 0.000 claims 2
- 102220495208 NAD(P)H pyrophosphatase NUDT13, mitochondrial_R12A_mutation Human genes 0.000 claims 2
- 102220495705 NAD(P)H pyrophosphatase NUDT13, mitochondrial_R13A_mutation Human genes 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- CEGWCSBNIDQYJA-UHFFFAOYSA-N n-(2-amino-3-fluoro-2-methylpropyl)-8-[(2,6-difluorophenyl)methoxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxamide;formic acid Chemical compound OC=O.C=1C(C)=CN2C(C(=O)NCC(C)(N)CF)=C(C)N=C2C=1OCC1=C(F)C=CC=C1F CEGWCSBNIDQYJA-UHFFFAOYSA-N 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 208000002815 pulmonary hypertension Diseases 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 230000009424 thromboembolic effect Effects 0.000 claims 2
- 208000019553 vascular disease Diseases 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 230000000702 anti-platelet effect Effects 0.000 claims 1
- 239000003146 anticoagulant agent Substances 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 230000036772 blood pressure Effects 0.000 claims 1
- MAPRDOKILZKGDP-UHFFFAOYSA-N bromo-chloro-iodomethanesulfonic acid Chemical compound OS(=O)(=O)C(Cl)(Br)I MAPRDOKILZKGDP-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000037356 lipid metabolism Effects 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 229940082615 organic nitrates used in cardiac disease Drugs 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
Classifications
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- A—HUMAN NECESSITIES
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- 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
- A61K31/435—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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
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- A61K31/439—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 the ring forming part of a bridged ring system, e.g. quinuclidine
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
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- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
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Claims (20)
1. ent-N-[(2S)-Amino-2-metilbutil]-8-[(2,6-difluorobenzil)oksi]-2,6-dimetilimidazo[1,2-a] piridin-3-karboksamid (Enantiomer A) ent-N-(2-Amino-2-metilbutil)-8-[(2,6-difluorobenzil)oksi]-2,6-dimetilimidazo[1,2-a]-piridin-3-karboksamid (Enantiomer B) ent-N-(2-amino-5,5,5-trifluoro-2-metilpentil)-2,6-dimetil-8-[(2,3,6-trifluorobenzil)oksi] imidazo[1,2-a]piridin-3-karboksamid (Enantiomer B) ent-N-(2-amino-5,5,5-trifluoro-2-metilpentil)-8-[(2,6-difluorobenzil)oksi]-2,6-dimetil imidazo[1,2-a]piridine-3-karboksamid (Enantiomer B) ent-N-(2-amino-5,5,5-trifluoro-2-metilpentil)-8-[(2,6-difluorobenzil)oksi]-2,6-dimetil imidazo[1,2-a]piridin-3-karboksamid (Enantiomer A) ent-N-(2-amino-3-fluoro-2-metilpropil)-2,6-dimetil-8-[(2,3,6-trifluorobenzil)oksi] imidazo[1,2-a]piridin-3-karboksamid (Enantiomer B) ent-N-(2-amino-3-fluoro-2-metilpropil)-8-[(2,6-difluorobenzil)oksi]-2,6-dimetilimidazo [1,2-a] piridin-3-karboksamid (Enantiomer B) ent-N-(2-amino-3-fluoro-2-metilpropil)-8-[(2,6-difluorobenzil)oksi]-2,6-dimetilimidazo[1,2-a]piridin-3-karboksamid (Enantiomer A) rac-N-(2-amino-3-fluoro-2-metilpropil)-8-[(2,6-difluorobenzil)oksi]-2,6-dimetilimidazo[1,2-a]piridin-3-karboksamid format ent-N-(2-amino-3-fluoro-2-metilpropil)-2,6-dimetil-8-[(2,3,6-trifluorobenzil)oksi]imidazo [1,2-a]piridin-3-karboksamid (Enantiomer A) ent-N-(2-amino-3-fluoro-2-metilpropil)-8-[(2,6-difluorobenzil)oksi]-6-(difluorometil)-2-metilimidazo[1,2-a]piridin-3-karboksamid (Enantiomer B) ent-N-(2-amino-3-fluoro-2-metilpropil)-8-[(2,6-difluorobenzil)oksi]-6-(difluorometil)-2-metilimidazo[1,2-a]piridin-3-karboksamid (Enantiomer A) ent-N-(2-amino-3-fluoro-2-metilpropil)-8-[(2,6-difluorobenzil)oksi]-6-(fluorometil)-2-metilimidazo[1,2-a]piridin-3-karboksamid
2. Jedinjenje prema zahtevu 1 ent-N-[(2S)-Amino-2-metilbutil]-8-[(2,6-difluorobenzil)oksi]-2,6-dimetilimidazo[1,2-a] piridin-3-karboksamid (Enantiomer A)
3. Jedinjenje prema zahtevu 1 ent-N-(2-Amino-2-metilbutil)-8-[(2,6-difluorobenzil)oksi]-2,6-dimetilimidazo[1,2-a]-piridin-3-karboksamid (Enantiomer B)
4. Jedinjenje prema zahtevu 1 ent-N-(2-amino-5,5,5-trifluoro-2-metilpentil)-2,6-dimetil-8-[(2,3,6-trifluorobenzil)oksi] imidazo[1,2-a]piridin-3-karboksamid (Enantiomer B)
5. Jedinjenje prema zahtevu 1 ent-N-(2-amino-5,5,5-trifluoro-2-metilpentil)-8-[(2,6-difluorobenzil)oksi]-2,6-dimetil imidazo[1,2-a]piridin-3-karboksamid (Enantiomer B)
6. Jedinjenje prema zahtevu 1 ent-N-(2-amino-5,5,5-trifluoro-2-metilpentil)-8-[(2,6-difluorobenzil)oksi]-2,6-dimetil imidazo[1,2-a]piridin-3-karboksamid (Enantiomer A)
7. Jedinjenje prema zahtevu 1 ent-N-(2-amino-3-fluoro-2-metilpropil)-2,6-dimetil-8-[(2,3,6-trifluorobenzil)oksi]imidazo [1,2-a]piridin-3-karboksamid (Enantiomer B)
8. Jedinjenje prema zahtevu 1 ent-N-(2-amino-3-fluoro-2-metilpropil)-8-[(2,6-difluorobenzil)oksi]-2,6-dimetilimidazo[1,2-a]piridin-3-karboksamid (Enantiomer B)
9. Jedinjenje prema zahtevu 1 ent-N-(2-amino-3-fluoro-2-metilpropil)-8-[(2,6-difluorobenzil)oksi]-2,6-dimetilimidazo[1,2-a]piridin-3-karboksamid (Enantiomer A)
10. Jedinjenje prema zahtevu 1 rac-N-(2-amino-3-fluoro-2-metilpropil)-8-[(2,6-difluorobenzil)oksi]-2,6-dimetilimidazo[1,2-a]piridin-3-karboksamid format
11. Jedinjenje prema zahtevu 1 ent-N-(2-amino-3-fluoro-2-metilpropil)-2,6-dimetil-8-[(2,3,6-trifluorobenzil)oksi]imidazo [1,2-a]piridin-3-karboksamid (Enantiomer A)
12. Jedinjenje prema zahtevu 1 ent-N-(2-amino-3-fluoro-2-metilpropil)-8-[(2,6-difluorobenzil)oksi]-6-(difluorometil)-2-metilimidazo[1,2-a]piridin-3-karboksamid (Enantiomer B)
13. Jedinjenje prema zahtevu 1 ent-N-(2-amino-3-fluoro-2-metilpropil)-8-[(2,6-difluorobenzil)oksi]-6-(difluorometil)-2-metilimidazo[1,2-a]piridin-3-karboksamid (Enantiomer A)
14. Jedinjenje prema zahtevu 1 ent-N-(2-amino-3-fluoro-2-metilpropil)-8-[(2,6-difluorobenzil)oksi]-6-(fluorometil)-2-metil imidazo[1,2-a]piridin-3-karboksamid
15. Postupak za dobijanje jedinjenja formule (I), prema zahtevu 1 do 14, naznačen time, što [A] jedinjenje formule (II) gde A, R1, R2, R4, R5 i R6 svaki imaju značenja koja su prethodno data i T1 predstavlja (C1-C4)-alkil ili benzil, reaguje u inertnom rastvaraču u prisustvu pogodne baze ili kiseline kako bi se dobila karboksilna kiselina formule (III) gde A, R1, R2, R4, R5 i R6 svaki imaju značenja koja su prethodno data, i ono potom reaguje u inertnom rastvaraču pod uslovima kuplovanja amida sa aminom formule (IV-A) ili (IV-B) gde L1A, L1B, L1C, L2, R7, R8, R9, i R10 svaki imaju značenja koja su prethodno data i R11A, R12A i R13A imaju značenja koja su porethodno data za R11, R12 i R13, respektivno, ili predstavljaju amino zaštitnu grupu, na primer terc-butoksikarbonil, benziloksikarbonil ili benzil, ili [B] jedinjenje formule (III-B) gde R2, R4, R5 i R6 svaki imaju značenja koja su prethodno data, reaguje u inertnom rastvaraču pod uslovima kuplovanja amida sa aminom formule (IV) kako bi se dobilo jedinjenje formule (I-A) i (I-B), gde R2, R4, R5, R6, L1A, L1B, L1C, L2, R7, R8, R9, R10, R11A, R12A i R13A svaki imaju značenja koja su prethodno data, iz ovog jedinjenja benzil grupa je naknadno uklonjena korišćenjem postupaka koji su poznati stručnjaku u tehnici i rezultujuće jedinjenje formule (V-A) ili (V-B) gde R2, R4, R5, R6, L1A, L1B, L1C, L2, R7, R8, R9, R10, R11A, R12A i R13A svaki imaju značenja koja su prethodno data, reaguje u inertnom rstvaraču u prisustvu pogodne baze sa jedinjenjem formule (VI) gde A i R1 imaju značenje koje je prethodno dato i X1 predstavlja odgovarajuću odlazeću grupu, prvenstveno hloro, bromo, jodo, mesilat, triflat ili tosilat, bilo koje prisutne zaštitne grupe su potom uklonjene, i rezultujuća jedinjenja formule (I) su opciono konvertovana sa odgovarajućim (i) rastvaračima i/ili (ii) kiselinama ili bazama u njihovim rastvaračima, solima i/ili solvatima soli.
16. Jedinjenje formule (I), prema bilo kom od zahteva 1 do 14, za lečenje i/ili profilaksu oboljenja.
17. Primena jedinjenja formule (I), prema bilo kom od zahteva 1 do 14, za proizvodnju medikamenta za lečenje i/ili profilaksu zastoja srca, angina pektoris, hipertenzije, pulmonarne hipertenzije, ishemije, vaskularnih poremećaja, zastoja bubrega, tromboeboličnih poremećaja i arterioskleroze.
18. Medikament koji sadrži jedinjenje formule (I), prema bilo kom od zahteva 1 do 14, u kombinaciji sa inertnom, ne toksičnom, farmaceutski prihvatljivom pomoćnom supstancom.
19. Medikament koji sadrži jedinjenje formule (I), prema bilo kom od zahteva 1 do 14, u kombinaciji sa drugim aktivnim jedinjenjem odabranim iz grupe koja se sastoji od organskih nitrata, NO-donora, cGMP-PDE inhibitora, agenasa koji imaju antitrombocitnu aktivnost, agenasa koji snižavaju krvni pritisak, i agenasa koji menjaju lipidni metabolizam.
20. Medikament prema zahtevu 18 ili 19 za lečenje i/ili profilaksu zastoja srca, angina pektoris, hipertenzije, pulmonarne hipertenzije, ishemije, vaskularnih poremećaja, zastoja bubrega, tromboeboličnih poremećaja i arterioskleroze.
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| PCT/EP2013/072891 WO2014068099A1 (de) | 2012-11-05 | 2013-11-04 | Amino-substituierte imidazo[1,2-a]pyridincarboxamide und ihre verwendung |
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2013
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