KR890006590A - 4-aminopyridine derivative - Google Patents

4-aminopyridine derivative Download PDF

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KR890006590A
KR890006590A KR1019880012933A KR880012933A KR890006590A KR 890006590 A KR890006590 A KR 890006590A KR 1019880012933 A KR1019880012933 A KR 1019880012933A KR 880012933 A KR880012933 A KR 880012933A KR 890006590 A KR890006590 A KR 890006590A
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KR900007243B1 (en
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챤드라신지 데자이 마노즈
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알렌제이. 스피겔
화이자 인코포레이티드
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Abstract

Compounds of formula (I), wherein R<1>, R<2>, A and B are defined hereinbelow. The compounds of the present invention inhibit brain acetylcholinesterase and are useful in the treatment of Alzheimer's disease.

Description

4-아미노피리딘 유도체4-aminopyridine derivative

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음As this is a public information case, the full text was not included.

Claims (10)

다음 일반식(Ⅰ)의 화합물 및 그의 약학적으로 허용되는 염.The compound of formula (I) and a pharmaceutically acceptable salt thereof. 상기식에서, A는 하기 일반식(1),(2),(3),(4) 및 (5)로 구성된 그룹으로 부터 선택하고Wherein A is selected from the group consisting of the following general formulas (1), (2), (3), (4) and (5) (여기에서, 일반식(1)의 a,b,c 및 d 위치에 있는 CH 잔기들중 하나는 질소원자로 치환되거나, a 및 d,a 및 c 또는 b 및 d 위치에 있는 CH 잔기 각각이 질소원자로 치환될 수 있다) : B는 하기 일반식(6),(7),(8),(9) 및 (10)으로 구성된 그룹으로 부터 선택하고Wherein one of the CH residues at positions a, b, c and d of Formula (1) is substituted with a nitrogen atom, or each of the CH residues at positions a and d, a and c or b and d is nitrogen May be substituted with an atom): B is selected from the group consisting of the following general formulas (6), (7), (8), (9) and (10) (여기에서, 점선은 각각 임의의 이중결합을 나타낸다) ; R1은 수소 또는 C1-C6알킬이고 ; R3는 수소, C1-C6알킬, C1-C6알콕시, C1-C6알칸오일, 디(C1-C6알킬아미노) -C1-C6알킬, C1-C6알콕시-C1-C6알킬, 할로겐, 하이드록시, 니트로, 페닐, 치환된 페닐, 페닐-C1-C6알킬, 치환된 페닐-C1-C6알킬, 디페닐-C1-C6알킬(여기서, 페닐그룹의 하나 또는 둘 모두가 치환된 페닐 그룹, 푸릴-C1-C6알킬, 티에닐-C1-C6알킬, 페닐옥시, 치환된 페닐옥시, NHCOR5및 NR6R7으로 치환될 수 있다)으로 구성된 그룹으로 부터 독립적으로 선택되고, 이때 상기 치환된 페닐 및 치환된 페닐알킬 그룹상의 페닐잔기는 할로겐, C1-C6알킬, 트리플루오로메틸, C1-C6알콕시-C1-C6알킬, 하이드록시 및 니트로로 구성된 그룹으로 부터 선택된 치환체 하나이상으로 치환되며, 또한, R5,R6및 R7은 C1-C6알킬 및 C1-C6알칸오일로 부터 독립적으로 선택되며 ; R2는 1,4-디하이드로피리딜-C1-C6알칸오일, C1-C6알킬-1,4-디하이드로피리딜-C1-C6-알칸오일 및 R3에 대한 상기 정의들(단,R2는 하이드록시, 할로겐, C1-C6알콕시,페닐옥시 또는 치환된 페닐옥시일수 없다)로 구성된 그룹으로 부터 독립적으로 선택되며 ; R4는 R3에 대한 상기 정의들(단, R4는 할로겐, 니트로, NHCOR5또는 NR6R7이 아니다)로 부터 독립적으로 선택되며 ; n은 1,2 또는 3이고 ; Z1은 NH,O, S 또는 NR8(이때 R8은 C1-C6알킬 또는 C1-C6알칸오일이다)이며 ; Z2는 O 또는 S이고 ; Z3및 Z4는 (CH2)p,O, S, S=O 및 SO2로 부터 독립적으로 선택되며, 단 Z3및 Z4중 적어도 하나는 (CH2)p이고 ; Z5는 CH2, O. S, S=O 또는 SO2이고고 ; Z6는O, S, S=O 또는 SO2이며 ; p는1,2 또는 3이고 ; q는 1 또는 2이며 , Y1은 CH2, CHOH, O, C=O, S, S=O 또는 SO2이고 ; Y2는 CH2, CH,O, S, S=O 또는 SO2이고 ; 및 Y3는 CHOH, CH2, CH 또는 C=O이며 단, 일반식(8)의 그룹은 Y2와 Y3가 모두 CH일때만 이중결합을 가지며, A가 R3는 수소이고 a, b, c 또는 d위치에 질소가 없는 일반식(1)의 그룹이거나 A가 일반식(3) 또는 (4)의 그룹일때 Y1및 Y2중 하나만이 CH2일수 있으며, A가 R3는 수소이고 a,b,c 또는 d 위치에 질소가 없는 일반식(1)의 그룹일 경우 Z3와 Z4중 하나만이 (CH2)p일수 있다.(Wherein, the dotted lines each represent an arbitrary double bond); R 1 is hydrogen or C 1 -C 6 alkyl; R 3 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 al Khan oil, di (C 1 -C 6 alkylamino) -C 1 -C 6 alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, halogen, hydroxy, nitro, phenyl, substituted phenyl, phenyl-C 1 -C 6 alkyl, substituted phenyl-C 1 -C 6 alkyl, diphenyl-C 1 -C 6 alkyl, where one or both of the phenyl groups are substituted, furyl-C 1 -C 6 alkyl, thienyl-C 1 -C 6 alkyl, phenyloxy, substituted phenyloxy, NHCOR 5 and NR 6 R 7 may be substituted with a) a is independently selected from the group consisting of, wherein the substituted phenyl and the phenyl moieties on the substituted phenylalkyl group is a halogen, C 1 -C 6 alkyl, trifluoromethyl, C 1 - C 6 alkoxy-C 1 -C 6 is substituted with one or more substituents selected from the group consisting of alkyl, hydroxy and nitro, wherein R 5, R 6 and R 7 are C 1 -C 6 alkyl and C 1 -C Independently selected from 6 alkanes; R 2 is the above for 1,4-dihydropyridyl-C 1 -C 6 alkanoyl, C 1 -C 6 alkyl-1,4-dihydropyridyl-C 1 -C 6 -alkanoyl and R 3 Are independently selected from the group consisting of definitions, provided that R 2 cannot be hydroxy, halogen, C 1 -C 6 alkoxy, phenyloxy or substituted phenyloxy; R 4 is independently selected from the above definitions for R 3 provided that R 4 is not halogen, nitro, NHCOR 5 or NR 6 R 7 ; n is 1,2 or 3; Z 1 is NH, O, S or NR 8 , wherein R 8 is C 1 -C 6 alkyl or C 1 -C 6 alkanoyl; Z 2 is O or S; Z 3 and Z 4 are independently selected from (CH 2 ) p , O, S, S═O and SO 2 , provided that at least one of Z 3 and Z 4 is (CH 2 ) p ; Z 5 is CH 2 , O. S, S═O or SO 2 ; Z 6 is O, S, S = O or SO 2 ; p is 1,2, or 3; q is 1 or 2 and Y 1 is CH 2 , CHOH, O, C═O, S, S═O or SO 2 ; Y 2 is CH 2 , CH, O, S, S═O or SO 2 ; And Y 3 is CHOH, CH 2 , CH or C═O, provided that the group of formula (8) has a double bond only when both Y 2 and Y 3 are CH, A is R 3 is hydrogen and a, b When one of the groups of formula (1) without nitrogen at position c or d or A is a group of formula (3) or (4), only one of Y 1 and Y 2 may be CH 2 , and A is R 3 And a group of formula (1) without nitrogen in a, b, c or d positions, only one of Z 3 and Z 4 may be (CH 2 ) p . 제1항에 있어서, A가 a,b,c 또는 d 위치에 질소가 없는 일반식(1)의 그룹이거나, A가 일반식(3) 또는 (4)의 그룹일때 Y1및 Y2중 하나만이 CH2일수 있음을 특징으로 하는 화합물.2. A compound according to claim 1, wherein A is a group of formula (1) without nitrogen at the a, b, c or d position, or only one of Y 1 and Y 2 when A is a group of formula (3) or (4) This CH 2 may be a compound. 제1항 또는 2항에 있어서, 언급한 화합물이 A가 일반식(1)의 그룹(여기에서, 일반식(1)의 a 및 b 위치에 있는 CH 잔기들중 하나가 질소원자에 의해 대치될 수 있다)이거나 A가 일반식(3)의 그룹이고 ; B, R1, R2, R3, R4,Z3,Z4,Z5,Y3및 q가 제1항에서 정의한 바와 같으며 ; n이 1 또는 2이고 ; Z6가 S이며 ; p는 1 또는 2이고, 단,(a) A가 a나 b 위치에 질소가 없는 일반식(1)의 그룹일때, Z3가 O, S 또는 CH2이며 ; R4가 수소 또는 C1-C6알킬이고 ; Z4가 (CH2)P(여기에서,p는 1 또는 2이다) 또는 S이며 ; Y1이 CH2, C=O, O 또는 S이고 ; Y2CH2,O 또는 S이고 단, Y1및 Y2중의 하나만이 CH2일수 있으며 ; (b) A가 a나 b위치에 질소가 있는 일반식(1)의 그룹일때, Y1는 O, S 또는 CH2이고 Y2는 CH2이며 ; 및 (c) A가 일반식(3)의 그룹일 경우, Y1는 O 또는 S이고 Y2는 CH2인 일반식(Ⅰ)화합물 및 그의 약학적으로 허용되는 염들로 이루어진 군중에서 선택됨을 특징으로 하는 화합물.3. A compound according to claim 1 or 2, wherein the compounds mentioned are those in which A is a group of formula (1) wherein one of the CH moieties at positions a and b of formula (1) is replaced by a nitrogen atom Or A is a group of general formula (3); B, R 1 , R 2 , R 3 , R 4 , Z 3 , Z 4 , Z 5 , Y 3 and q are as defined in claim 1; n is 1 or 2; Z 6 is S; p is 1 or 2, provided that (a) when A is a group of the general formula (1) without nitrogen at the a or b position, Z 3 is O, S or CH 2 ; R 4 is hydrogen or C 1 -C 6 alkyl; Z 4 is (CH 2 ) P (where p is 1 or 2) or S; Y 1 is CH 2 , C═O, O or S; Y 2 CH 2, O or S, and the only one of the stages, Y 1 and Y 2 are CH 2 days; (b) when A is a group of formula (1) with nitrogen at the a or b position, Y 1 is O, S or CH 2 and Y 2 is CH 2 ; And (c) when A is a group of formula (3), Y 1 is selected from the group consisting of a compound of formula (I) and pharmaceutically acceptable salts thereof, wherein Y 1 is O or S and Y 2 is CH 2 Compound made into. 제1항 내지 3항중 어느 한 항에 있어서, B가 일반식(7) 또는 (8)의 그룹임을 특징으로 하는 화합물.The compound according to any one of claims 1 to 3, wherein B is a group of formula (7) or (8). 제 4 항에 있어서, R1, R2및 R4가 수소이고 R3가 수소 또는 할로겐인 화합물.The compound of claim 4, wherein R 1 , R 2 and R 4 are hydrogen and R 3 is hydrogen or halogen. 제1항에 있어서, A가 일반식(1)의 그룹(이때 R3는 일반식(Ⅰ)에 대해 상기 정의한 바와 같고, 다만 R3는 일반식(1)의 c 위치에반 존재할 수 있다)이고, R1, R2및 B가 제1항에서 정의한 바와 같은 화합물.The method of claim 1 wherein, A is a group of formula (1) (wherein R 3 is as defined above for formula (Ⅰ), but R 3 may be present Evan c position of the general formula (1)) and , R 1 , R 2 and B are as defined in claim 1. 제1항에 있어서, A가 일반식(1)의 그룹(이때 R3는 C1-C6알킬, C1-C6알콕시 ,할로겐,하이드록시, 니토로, NHCOR5, NR6R7또는 트리플루오로메틸이고, R5,R6및 R7은 제1항에서 정의한 바와 같다)이며 ; B가 일반식r(이때 r은 2,3 또는 4이다)의 그룹인 화합물.The compound of claim 1, wherein A is a group of formula (1) wherein R 3 is C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halogen, hydroxy, nitoro, NHCOR 5 , NR 6 R 7 or Trifluoromethyl, and R 5 , R 6 and R 7 are as defined in claim 1; B is a general formula A compound that is a group of r wherein r is 2, 3 or 4. 제1항에 있어서, 언급한 화합물이 8-플루오로-9-아미노-1,2,3,4-테트라하이드로아크리딘 또는 그의 약학적으로 허용되는 염임을 특징으로 하는 화합물.The compound according to claim 1, wherein the compound mentioned is 8-fluoro-9-amino-1,2,3,4-tetrahydroacridine or a pharmaceutically acceptable salt thereof. 제1항에 따른 화합물을 포함함을 특징으로 하는 약학조성물.A pharmaceutical composition comprising the compound of claim 1. 알쯔하이머 병(Alzheimer's disease)의 치료를 위한 제1항에 따른 화합물.A compound according to claim 1 for the treatment of Alzheimer's disease. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019880012933A 1987-10-05 1988-10-04 4-amino pyridine derivatives KR900007243B1 (en)

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