ME01982B - 2-anilinobenzimidazol-6-karboksamidi kao anti-inflamatorni agensi - Google Patents

2-anilinobenzimidazol-6-karboksamidi kao anti-inflamatorni agensi

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Publication number
ME01982B
ME01982B MEP-2015-2A MEP215A ME01982B ME 01982 B ME01982 B ME 01982B ME P215 A MEP215 A ME P215A ME 01982 B ME01982 B ME 01982B
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group
groups
optionally substituted
substituents selected
3alkyl
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MEP-2015-2A
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Henning Priepke
Henri Doods
Raimund Kuelzer
Roland Pfau
Dirk Stenkamp
Benjamin Pelcman
Robert Roenn
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Boehringer Ingelheim Int
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Publication of ME01982B publication Critical patent/ME01982B/me

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Claims (16)

1. Jedinjenje opšte formule I:u komeR1 i R2 nezavisno predstavljaju halogenu ili -C1-3 alkil grupu, pri čemu alkil grupa može biti opciono supstituisana sa jednim ili sa više atoma fluora;W predstavlja -C(O)-, -C(O)O- grupe vezane za azot -NH- grupe preko atoma ugljenika;M predstavlja-C1-6alkil ili -C3-7cikloalkil grupu, pri čemu obe grupe mogu biti opciono supstituisane sa jednom ili sa više grupa izabranih iz grupe koju čine -F, -OH, -CN, -NH2, -NH(C1-2alkil) , -N(C1-2alkil)2, -OC1-3alkil, -C1-5alkil i -C3-4cikloalkil grupe, a poslednje tri navedene alkil ili cikloalkil grupe mogu biti dalje opciono supstituisane sa jednim ili sa više atoma fluora; ili predstavlja oksetanil-, tetrahidrofuranil-, tetrahidropiranil-, azetidinil-, pirolidinil-, piperidinil- grupu, pri čemu svaka od ovih grupa može biti opciono supstituisana sa jednim ili sa više supstituenata izbaranih iz grupe koju čine fluoro, -CN i -C1-3alkil grupa, a alkil grupa može biti opciono supstituisana sa jednim ili sa više atoma fluora;ili predstavlja fenil-, piridil-, tienil-, pirolil-, pirazolil-, imidazolil-, tiazolil-, oksazolil- ili izoksazolil-grupu, pri čemu svaka od navedenih grupa može biti opciono supstituisana sa jednim ili sa više supstituenata izabranih iz grupe koju čine halogena, -CN ili -C1-3alkil grupa, a poslednje navedena alkil grupa dalje može biti opciono supstituisana sa jednim ili sa više atoma fluora;R8 predstavlja -H, halogenu ili -C1-3alkil grupu, pri čemu poslednje navedena alkil grupa može biti opciono supstituisana sa jednim ili sa više atoma fluora;R6 predstavlja -H, -C1-5alkil ili -C3-7cikloalkil-C0-2alkil grupu, pri čemu tri poslednje navedene alkil ili cikloalkil grupe mogu biti opciono supstituisane sa jednim ili sa više atoma fluora;R7 predstavlja halogenu, C1-5alkil-O-, -C3-7cikloalkil-C0-2 alkil-O-, 4-7-članu heterocikloalkil-C0-2alkil-O- grupu, pri čemu tri poslednje navedene alkil, cikloalkil ili heterocikloalkil grupe mogu biti opciono supstituisane sa jednim ili sa više supstituenata izabranih iz grupe koju čine -F i -OC1-3alkil grupa; alkil grupa dalje može opciono biti supstituisana sa jednim ili sa više atoma fluora;A predstavlja C1-8alkil-, fenil-, indanil-, naftil-, 1,2,3,4-tetrahidronaftil-, piridil-, tienil, benzotienil-, pirolil-, indolil-pirazolil-, indazolil-, tiazolil- , benzotiazolil-, oksazolil-, benzoksazolil-, izoksazolil-, benzizoksazolil-, fenil-C1-3alkil-, tienil-C1-3alkil-, piridil-C1-3alkil, C3-7cikloalkil-C0-3alkil-, oksetanil-C0-3alkil-, tetrahidrofuranil-C0-3alkil ili tetrahidropiranil-C0-3alkil grupu, pri čemu alkil-, cikloalkil- i heterocikloalkil radikali mogu biti opciono supstituisani sa jednim ili sa više supstituenata izabranih iz grupe koja je označena kao R9a, dok aril i heteroaril radikali mogu biti opciono supstituisani sa jednim ili sa više supstituenata izabranih iz grupe koja je označena kao R9b;svaki R9a nezavisno predstavlja -F, -Cl ili -C1-3alkil grupu koja opciono može biti supstituisana sa jednim ili sa više supstituenata izabranih između -F i -OC1-3alkil grupe;svaki R9b predstavlja nezavisno -halogenu, -CN ili -C1-3alkil grupu koja opciono može biti supstituisana sa jednim ili sa više atoma fluora;ili so navedenog jedinjenja.
2. Jedinjenje prema patentnom zahtevu 1, naznačeno time, što R8 predstavlja -H ili fluoro grupu.
3. Jedinjenje prema patentnim zahtevima 1 ili 2, naznačeno time, što R6 predstavlja -H, -CH3 ili ciklopropil grupu.
4. Jedinjenje prema bilo kom od prethodno navednih patentnih zahteva, naznačeno time, što R1 i R2 nezavisno predstavljaju hloro, fluoro, -CH3, -CH2F, -CHF2 i -CF3 grupu.
5. Jedinjenje prema bilo kom od prethodno navednih patentnih zahteva, naznačeno time, što R7 predstavlja fluoro, -OCHF2, -OCF3, -OCH2CH2F, -OCH2CHF2, -OCH2CF3, -O-tetrahidrofuran-3-il ili -O-CH2-ciklopropil grupu.
6. Jedinjenje prema bilo kom od prethodno navednih patentnih zahteva, naznačeno time, što A predstavlja C1-4alkil-, C3-7cikloalkil-C0-2alkil-, tetrahidrofuranil-metil-, fenil-C1-2alkil-, piridil-metil-, fenil-, indanil-, piridil-, tienil-, tiazolil- ili benzotiazolil- grupu, pri čemu alkil-, cikloalkil- i heterocikloalkil- radikali opciono mogu biti supstituisani sa jednim ili sa više supstituenata izbranim iz grupe koju čine -F, -CH3, -CH2F, -CHF2 i -CF3 , a aril i heteroaril radikali opciono mogu biti supstituisani sa jednim ili sa više supstituenata izbranim iz grupe koju čine -F, -Cl, -Br, -CN, -CH3, -CH2F, -CHF2 i -CF3 grupa.
7. Jedinjenje prema bilo kom od prethodno navednih patentnih zahteva, naznačeno time, što M predstavlja C1-4alkil ili -C3-5cikloalkil grupu, pri čemu obe grupe mogu biti opciono supstituisane sa jednom ili sa više grupa izabranih od -F, -OH, -CN, -NH2, -OCH3, -CH3, -CH2F, -CHF2, -CF3 i ciklopropil grupe; ili predstavlja oksetanil-, tetrahidrofuranil-, azetidinil- ili pirolidinil- grupu, a svaka od ovih grupa može biti opciono supstituisana sa jednim ili sa više supstituenata izabranih iz grupe koju čine -F, -CH3, -CH2 F, -CHF2 i -CF3 grupa; ili predstavlja fenil-, indanil-, tienil, pirolil-, pirazolil-, imidazolil-, tiazolil- ili izoksazolil- grupu, pri čemu sve od navednih grupa opciono mogu biti supstituisane sa jednim ili sa više supstituenata izabranih iz grupe koju čine -F, -Cl, -CH3, -CH2F, -CHF2 i -CF3 grupa.
8. Jedinjenje prema bilo kom od prethodno navednih patentnih zahteva, a preciznije jedinjenje opšte formule la u kome M predstavlja metil, etil, propil, i-propil, n-butil, s-butil, t-butil, -CH2-ciklopropil, ciklopropil, ciklobutil ili ciklopentil grupu, pri ćemu sve od navednih grupa opciono mogu biti supstituisane sa jednom ili sa više grupa izabranih iz grupe koju čine -F , -OH, -CN, -NH2, -OCH3, -CH3 i -CF3 grupa; ili je izabran iz grupe koju čine sledeći radikali pri čemu svih devet navednih grupa opciono može biti supstituisano sa jednim ili sa više supstituenata izabranih iz grupe koju čine -F, -CH3 i -CF3 grupa; ili je izabran iz grupe radikala koja sledi: pri čemu svaka od navedenih jedanaest grupa može biti opciono supstituisana sa jednim ili sa više supstituenata izabranih iz grupe koju čine -F, -Cl, -CH3 i -CF3 grupa; a A, R1, R2, R6, R7 imaju isto značenje kao što je to definisano u bilo kom od prethodnih patentnih zahteva.
9. Jedinjenje prema patentnom zahtevu 8, naznačeno time, što A predstavlja metil, etil, propil, i-propil, n-butil, s-butil ili t-butil grupu, pri čemu sve od navedenih sedam grupa opciono mogu biti supstituisane sa jednim ili sa više atoma fluora, ili predstavlja ciklopropil, ciklobutil, ciklopentili ili cikloheksil grupu, naznačenu time, što poslednje od četiri navedene grupe mogu biti opciono supstituisane sa jednim ili sa više supstituenata odabranih iz grupe koju čine -F, -CH3, -CHF2 i -CF3 grupa; ili je izabran iz grupe radikala koja sledi: pri čemu sve od navedenih sedam grupa mogu biti opciono supstituisano sa jednim ili sa više supstituenata izabranih iz grupe koju čine -F, -CH3, -CHF2 i -CF3 grupa; ili je izabran iz grupe radikala koja sledi: pri čemu u svim od navedenih jedanaest grupa, arilni ili heteroarilni radikali mogu biti opciono supstituisani sa jednim ili sa više supstituenata izabranih iz grupe koju čine -F, -Cl, -Br, -CN, -CH3, i -CF3 grupa;
10. Jedinjenje prema bilo kom od prethodno navednih patentnih zahteva, preciznije jedinjenje opšte formule Ia ili Ib u kojima R1 i R2 nezavisno predstavljaju hloro, fluoro, -CH3, -CH2F, -CHF2 i -CF3 grupu; R6 predstavlja -H, -CH3 ili ciklopropil grupu; R7 predstavlja fluoro, -OCHF2, -OCF3, -OCH2CH2F, -OCH2CHF2, -OCH2CF3, tetrahidrofuran-3-il-O- ili -O-CH2-ciklopropil grupu; A predstavlja metil, etil, propil, i-propil, n-butil, s-butil ili t-butil grupu, pri čemu navedene grupe mogu biti opciono supstituisano sa jednim ili sa više atoma fluora, ili predstavlja ciklopropil, ciklobutil, ciklopentil, cikloheksil grupu, pri čemu navedene četiri grupe mogu biti opciono supstituisane sa jednim ili sa više supstituenata izabranih iz grupe koju čine -F, -CH3, -CHF2 i -CF3 grupa; li je izabran iz grupe radikala koja sledi: pri čemu navedenih sedam grupa može biti opciono supstituisano sa jednim ili sa više supstituenata izabranih iz grupe koju čine -F, -CH3, -CHF2 i -CF3 grupa; ili predstavlja jednu od sledećih grupa: pri čemu u svih navedenih jedanaest grupa, aril i heteroaril radikali opciono mogu biti supstituisani sa jednim ili sa više supstituenata izabranih iz grupe koju čine -F, -Cl, -Br, -CN, -CH3 i -CF3 grupa; M predstavlja metil, etil, propil, i-propil, n-butil, s-butil, t-butil, ciklopropil, -CH2-ciklopropil, ciklobutil ili ciklopentil grupu, pri čemu bilo koja od navedenih grupa može biti opciono supstituisana sa jednim ili sa više grupa izabranih iz grupe koju čine -F, -OH, -CN, -NH2, -OCH3, -CH3 i -CF3 grupa; ili grupu izabranu od sledećih: pri čemu navedenih devet grupa može biti opciono supstituisano sa jednim ili sa više supstituenata izabranih iz grupe koju čine -F, -CH3, -CHF2 i -CF3 grupa; ili predstavlja grupu izabranu od sledećih: pri čemu navedenih jedanaest grupa može biti opciono supstituisano sa jednim ili sa više supstituenata izabranih iz grupe koju čine -F, -Cl, -CH3 i -CF3 grupa;
11. Jedinjenje prema bilo kom od prethodno navednih patentnih zahteva izabrano iz grupe koju čine Struktura Struktura 1 6 2 7 3 8 4 9 5 10 11 16 12 17 13 18 14 19 15 20 21 26 22 27 23 28 24 29 25 30 31 36 32 37 33 38 34 39 35 40 41 46 42 47 43 48 44 49 45 50 51 56 52 57 53 58 54 59 55 60 61 66 62 67 63 68 64 69 65 70 71 72 73 79 74 80 75 81 76 82 77 83 78 84 85 91 86 92 87 93 88 94 89 95 90 96 97 103 98 104 99 105 100 106 101 107 102 108 109 115 110 116 111 117 112 118 113 119 114 120 121 127 122 128 123 129 124 130 125 131 126 132 133 139 134 140 135 141 136 142 137 143 138 144 145 152 146 153 147 154 148 155 149 156 150 157 151 158 159 166 160 167 161 168 162 169 163 170 164 171 165 172 173 180 174 181 175 182 176 177 178 179
12. Jedinjenje prema bilo kom od prethodno navednih patentnih zahteva za upotrebu u vidu medikamenta.
13. Farmaceutski preparat koji sadrže najmanje jedno od jedinjenja definisano bilo kojim od patentnih zahteva od 1 do 11, ili njegovu farmaceutski prihvatljivu so, u smeši sa farmaceutski prihvatljivim adjuvansom, diluentom i/ili nosačem.
14. Jedinjenje prema bilo kom od patentnih zahteva od 1 do 11 ili njegova farmaceutski prihvatljiva so za upotrebu u tretmanu i/ili prevenciji inflamatornih oboljenja i/ili srodnih stanja, a prevashodno inflamatornog bola.
15. Intermedijer opšte formule XIb, XIc, XVIIb, XVIIc, XIX ili XX u kome R1 i R2 nezavisno predstavljaju hloro, fluoro ili -CH3 grupu; M predstavlja metil, etil, propil, i-propil, n-butil, s-butil, t-butil, -CH2-ciklopropil, ciklopropil, ciklobutil ili ciklopentil grupu, pri ćemu sve od navednih grupa opciono mogu biti supstituisane sa jednom ili sa više grupa izabranih iz grupe koju čine -F , -OH, -CN, -NH2, -OCH3, -CH3 i -CF3 grupa; ili je izabran iz grupe radikala koja sledi: pri čemu svaka od navedenih grupa može biti opciono supstituisana sa jednim ili sa više supstituenata izabranih iz grupe koju čine -F, -CH3 ili -CF3 grupa, ili je izabran iz grupe radikala koja sledi: pri čemu svaka od navedenih grupa može biti opciono supstituisana sa jednim ili sa više supstituenata izabranih iz grupe koju čine -F, -Cl, -CH3 ili -CF3 grupa.
16. Intermedijer prema patentnom zahtevu 15, izabran iz grupe koju čine jedinjenja:
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US8759537B2 (en) 2014-06-24
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AU2011290725A1 (en) 2013-01-10
PT2606036E (pt) 2015-02-06
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