KR20050086516A - 호중구 엘라스타제의 억제제로서의 2-피리돈 유도체 - Google Patents
호중구 엘라스타제의 억제제로서의 2-피리돈 유도체 Download PDFInfo
- Publication number
- KR20050086516A KR20050086516A KR1020057008383A KR20057008383A KR20050086516A KR 20050086516 A KR20050086516 A KR 20050086516A KR 1020057008383 A KR1020057008383 A KR 1020057008383A KR 20057008383 A KR20057008383 A KR 20057008383A KR 20050086516 A KR20050086516 A KR 20050086516A
- Authority
- KR
- South Korea
- Prior art keywords
- methyl
- phenyl
- carboxamide
- oxo
- dihydropyridine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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- 239000003112 inhibitor Substances 0.000 title abstract description 11
- 102000016387 Pancreatic elastase Human genes 0.000 title description 8
- 108010067372 Pancreatic elastase Proteins 0.000 title description 8
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 title description 4
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- -1 R 21 Chemical compound 0.000 claims description 129
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- CDEBWUKPPGESTE-UHFFFAOYSA-N n-(2-hydroxyethyl)-2,4-dioxo-3-phenyl-1h-pyrimidine-5-carboxamide Chemical compound O=C1C(C(=O)NCCO)=CNC(=O)N1C1=CC=CC=C1 CDEBWUKPPGESTE-UHFFFAOYSA-N 0.000 claims description 2
- HADHYSLATZGMOO-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2,4-dioxo-3-phenyl-1h-pyrimidine-5-carboxamide Chemical compound O=C1C(C(=O)NCCN(C)C)=CNC(=O)N1C1=CC=CC=C1 HADHYSLATZGMOO-UHFFFAOYSA-N 0.000 claims description 2
- DJADWRUXZAZMCS-UHFFFAOYSA-N n-benzyl-5,6-dimethyl-2-oxo-1-phenylpyridine-3-carboxamide Chemical compound O=C1N(C=2C=CC=CC=2)C(C)=C(C)C=C1C(=O)NCC1=CC=CC=C1 DJADWRUXZAZMCS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 63
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 51
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 51
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- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 32
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- HVKBQTHYHKBPOG-UHFFFAOYSA-N 6-methyl-2-oxo-n-[(4-sulfanylphenyl)methyl]-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=CC=C1C(=O)NCC1=CC=C(S)C=C1 HVKBQTHYHKBPOG-UHFFFAOYSA-N 0.000 description 27
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- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 14
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Abstract
Description
화합물 | 인간 호중구 엘라스타제의 억제 IC50 (nM) |
1-(3-브로모페닐)-N-(4-메톡시벤질)-6-메틸-2-옥소-1,2-디히드로피리딘-3-카르복스아미드 | 353 |
6-메틸-N-[(5-메틸이속사졸-3-일)메틸]-2-옥소-1-[3-(트리플루오로메틸)페닐]-1,2-디히드로피리딘-3-카르복스아미드 | 318 |
N-(2,3-디메톡시벤질)-6-메틸-2-옥소-1-[3-(트리플루오로메틸)페닐]-1,2-디히드로피리딘-3-카르복스아미드 | 701 |
N-(2,3-디히드로-1-벤조푸란-5-일메틸)-2,4-디옥소-3-[3-(트리플루오로메틸)페닐]-1,2,3,4-테트라히드로피리미딘-5-카르복스아미드 | 2025 |
Claims (10)
- N-벤질-5,6-디메틸-2-옥소-1-페닐-1,2-디히드로피리딘-3-카르복스아미드;N-(2-펜에틸)-5,6-디메틸-2-옥소-1-페닐-1,2-디히드로피리딘-3-카르복스아미드;N-(2-히드록시에틸)-2,4-디옥소-3-페닐-1,2,3,4-테트라히드로피리미딘-5-카르복스아미드;N-[2-(디메틸아미노)에틸]-2,4-디옥소-3-페닐-1,2,3,4-테트라히드로피리미딘-5-카르복스아미드;4-[2-[[[1,2-디히드로-1-(4-메틸시클로헥실)-2-옥소-3-피리디닐]카르보닐]아미노]에틸]-벤조산; 및4-[2-[[(1-시클로헥실-1,2-디히드로-2-옥소-3-피리디닐]카르보닐]아미노]에틸]-벤조산을 제외한,하기 화학식 I의 화합물 및 그의 제약상 허용되는 염.<화학식 I>식 중,X는 O 또는 S를 나타내고;Y1은 N 또는 CR2를 나타내고; R1이 OH를 나타내는 경우에 Y1은 또한 호변이성질체 형태로 NR6을 나타낼 수 있고;Y2는 CR3을 나타내고; Y1이 CR2를 나타내는 경우에 Y2는 또한 N을 나타낼 수 있고;R1은 H 또는 C1 내지 6 알킬을 나타내며; 여기서 상기 알킬은 할로겐, CN, CHO, OR7, NR8R9, S(O)mR10 및 SO2NR11R12로부터 독립적으로 선택되는 하나 이상의 치환체에 의해 임의로 치환되고;Y1이 N을 나타내는 경우에 R1은 또한 OH를 나타낼 수 있고;R7은 H, C1 내지 6 알킬 또는 페닐을 나타내며; 상기 페닐은 할로겐, C1 내지 6 알킬 및 C1 내지 6 알콕시에 의해 임의로 추가로 치환되고;R2는 H, 할로겐 또는 C1 내지 6 알킬을 나타내고;R3은 H 또는 F를 나타내고;G1은 페닐 또는 O, S 및 N으로부터 독립적으로 선택되는 1 내지 3개의 헤테로원자를 함유하는 5- 또는 6-원의 헤테로방향족 고리를 나타내고; 또는 G1은 5- 또는 6-원의 포화 또는 부분적으로 불포화된 시클로알킬 고리를 나타내거나; 또는 G1은 O, S 및 NR13으로부터 선택되는 1개의 헤테로원자를 함유하는 5- 또는 6-원의 포화 또는 부분적으로 불포화된 헤테로시클릭 고리를 나타내며, 여기서 R13은 H 또는 C1 내지 6 알킬을 나타내고;R5는 H, 할로겐, C1 내지 6 알킬, CN, C1 내지 6 알콕시, NO2, NR14R15, 1개 이상의 F 원자에 의해 치환되는 C1 내지 3 알킬 또는 1개 이상의 F 원자에 의해 치환되는 C1 내지 3 알콕시를 나타내고;R14 및 R15는 독립적으로 H 또는 C1 내지 3 알킬을 나타내며; 여기서 상기 알킬은 1개 이상의 F 원자에 의해 임의로 추가로 치환되고;n은 정수 1, 2 또는 3을 나타내고, n이 2 또는 3을 나타내는 경우에 각각의 R5 기는 독립적으로 선택되고;R4 및 R6은 독립적으로 H 또는 C1 내지 6 알킬을 나타내며; 여기서 상기 알킬은 OH 또는 C1 내지 6 알콕시에 의해 임의로 추가로 치환되거나; 또는R4 및 L은 -NR4L기가 O, S 및 NR16으로부터 선택되는 1개의 추가 헤테로원자를 임의로 포함한 5 내지 7원의 아자시클릭 고리를 나타내도록 서로 결합하고;L은 결합, O, NR29 또는 C1 내지 6 알킬을 나타내며; 여기서 상기 알킬은 O, S 및 NR16으로부터 선택되는 1개의 헤테로원자를 임의로 포함하고; 상기 알킬은 OH 또는 OMe에 의해 임의로 추가로 치환되고;G2는i) 페닐 또는 페녹시,ii) O, S 및 N으로부터 독립적으로 선택되는 1 내지 3개의 헤테로원자를 함유하는 5 또는 6원의 헤테로방향족 고리,iii) C3 내지 6 포화 또는 부분적으로 불포화된 시클로알킬, 또는iv) O, S(O)p 및 NR17로부터 독립적으로 선택되는 1 또는 2개의 헤테로원자를 함유하고 카르보닐기를 임의로 추가로 포함하는 C4 내지 7 포화 또는 부분적으로 불포화된 헤테로시클릭 고리로부터 선택되는 모노시클릭 고리계를 나타내거나; 또는G2는 2개의 고리가 각각i) 페닐,ii) O, S 및 N으로부터 독립적으로 선택되는 1 내지 3개의 헤테로원자를 함유하는 5 또는 6원의 헤테로방향족 고리,iii) C3 내지 6 포화 또는 부분적으로 불포화된 시클로알킬, 또는iv) O, S(O)p 및 NR17으로부터 독립적으로 선택되는 1 또는 2개의 헤테로원자를 함유하고 카르보닐기를 임의로 추가로 포함하는 C4 내지 7 포화 또는 부분적으로 불포화된 헤테로시클릭 고리로부터 독립적으로 선택되는 비시클릭 고리계를 나타내고,상기 2개의 고리는 함께 융합되거나 또는 함께 직접적으로 결합되거나, 또는 O, S(O)q 또는 CH2로부터 선택되는 연결기에 의해 분리되며, 여기서상기 모노시클릭 또는 비시클릭 고리계는 CN, OH, C1 내지 6 알킬, C1 내지 6 알콕시, 할로겐, NR18R19, NO2, OSO2R38, CO2R20, C(=NH)NH2, C(O)NR21R22, C(S)NR23R24, SC(=NH)NH2, NR31C(=NH)NH2, S(O)sR25, SO2NR26R27, 1개 이상의 F 원자에 의해 치환되는 C1 내지 3 알콕시 및 SO2R39 또는 1개 이상의 F 원자에 의해 치환되는 C1 내지 3 알킬로부터 독립적으로 선택되는 1 내지 3개의 치환체에 의해 임의로 추가로 치환되거나; 또는L이 결합을 나타내지 않는 경우에 G2는 H를 나타낼 수도 있고;m, p, q, s 및 t는 독립적으로 정수 0, 1 또는 2를 나타내고;R8 및 R9는 독립적으로 H, C1 내지 6 알킬, 포르밀 또는 C2 내지 6 알카노일을 나타내며; 여기서 상기 알킬은 할로겐, C1 내지 6 알킬, C1 내지 6 알콕시 또는 SO2R30에 의해 임의로 치환되는 페닐에 의해 임의로 추가로 치환되거나; 또는NR8R9기는 함께 O, S 및 NR28로부터 선택되는 1개의 추가 헤테로원자를 임의로 포함하는 5 내지 7원의 아자시클릭 고리를 나타내고;R18 및 R19는 H, C1 내지 6 알킬, 포르밀, C2 내지 6 알카노일, S(O)tR32 또는 SO2NR33R34를 독립적으로 나타내며; 여기서 상기 알킬기는 할로겐, CN, C1 내지 4 알콕시 또는 CONR41R42에 의해 임의로 추가로 치환되고;R25는 H, C1 내지 6 알킬 또는 C3 내지 6 시클로알킬을 나타내며; 상기 알킬기는 OH, CN, CONR35R36, CO2R37, OCOR40, C3 내지 6 시클로알킬, O, S(O)p 및 NR43으로부터 독립적으로 선택되는 1 또는 2개의 헤테로원자를 함유하는 C4 내지 7 포화 헤테로시클릭 고리, 및 O, S 및 N으로부터 독립적으로 선택되는 1 내지 3개의 헤테로원자를 함유하는 페닐 또는 5 또는 6원의 헤테로방향족 고리로부터 독립적으로 선택되는 하나 이상의 치환체에 의해 임의로 추가로 치환되며; 여기서 상기 방향족 고리는 할로겐, CN, C1 내지 4 알킬, C1 내지 4 알콕시, OH, CONR44R45, CO2R46, S(O)sR47 및 NHCOCH3으로부터 독립적으로 선택되는 하나 이상의 치환체에 의해 임의로 추가로 치환되고;R26 및 R27은 독립적으로 H, C1 내지 6 알킬, 포르밀 또는 C2 내지 6 알카노일을 나타내고;R32는 H, C1 내지 6 알킬 또는 C3 내지 6 시클로알킬을 나타내고;R38은 H, C1 내지 6 알킬 또는 페닐을 나타내며; 여기서 상기 페닐은 할로겐, C1 내지 6 알킬 또는 C1 내지 6 알콕시에 의해 임의로 추가로 치환되고;R10, R11, R12, R16, R17, R20, R21, R22, R23, R24, R28, R29, R30, R31, R33, R34, R35, R36, R37, R39, R40, R41, R42, R43, R44, R45, R46 및 R47은 독립적으로 H 또는 C1 내지 6 알킬을 나타낸다.
- 제1항에 있어서, X가 O를 나타내는 화합물.
- 제1항 또는 제2항에 있어서, R2 및 R3이 각각 H를 나타내는 화합물.
- 제1항 내지 제3항 중 어느 한 항에 있어서, G1이 페닐 또는 피리딜을 나타내는 화학식 I의 화합물.
- 제1항에 있어서, 의약으로서 사용하기 위한 화학식 I의 화합물 또는 그의 제약상 허용되는 염.
- 제1항 내지 제4항 중 어느 한 항에 정의된 화학식 I의 화합물 또는 그의 제약상 허용되는 염을 임의로 제약상 허용되는 희석제 또는 담체와의 혼합물로 포함하는 제약 제제.
- 호중구 엘라스타제 활성의 억제가 유익한 인간 질환 또는 증상을 앓고 있거나 그에 민감한 인간에게 치료 유효량의 제1항 내지 제4항 중 어느 한 항에 정의된 화학식 I의 화합물 또는 그의 제약상 허용되는 염을 투여하는 것을 포함하는, 상기 질환 또는 증상을 치료하거나 또는 그의 위험을 저하시키는 방법.
- 호중구 엘라스타제 활성의 억제가 유익한 인간 질환 또는 증상의 치료용 또는 예방용 의약의 제조에서의 제1항 내지 제4항 중 어느 한 항에 정의된 화학식 I의 화합물 또는 그의 제약상 허용되는 염의 용도.
- 염증 질환 또는 증상의 치료용 또는 예방용 의약의 제조에서의 제1항 내지 제4항 중 어느 한 항에 정의된 화학식 I의 화합물 또는 그의 제약상 허용되는 염의 용도.
- 하기 화학식 II의 화합물을 하기 화학식 III의 아민 또는 그의 염과 반응시키는 것, 및경우에 따라 또는 필요한 경우, 생성된 화학식 I의 화합물 또는 그의 또다른 염을 그의 제약상 허용되는 염으로 전환시키거나; 또는 화학식 I의 화합물을 화학식 I의 또다른 화합물로 전환시키는 것; 및 경우에 따라, 생성된 화학식 I의 화합물을 그의 광학 이성질체로 전환시키는 것을 포함하는, 제1항 내지 제4항 중 어느 한 항에 정의된 화학식 I의 화합물, 및 그의 광학 이성질체, 라세미체 및 호변이성질체 및 그의 제약상 허용되는 염의 제조 방법.<화학식 II><화학식 III>식 중,R1, R4, R5, Y1, Y2, X, G1, G2, L 및 n은 제1항에 정의된 바와 같고,L1은 이탈기를 나타낸다.
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BR0316081A (pt) | 2005-09-27 |
IS2478B (is) | 2008-12-15 |
IS7867A (is) | 2005-05-26 |
RU2328486C2 (ru) | 2008-07-10 |
NO20052818L (no) | 2005-07-11 |
EP1562902A1 (en) | 2005-08-17 |
NZ539787A (en) | 2006-11-30 |
AU2003276802B2 (en) | 2007-03-08 |
CA2504766A1 (en) | 2004-05-27 |
ATE325096T1 (de) | 2006-06-15 |
MXPA05004818A (es) | 2005-07-22 |
ES2262029T3 (es) | 2006-11-16 |
SI1562902T1 (sl) | 2006-08-31 |
AR042024A1 (es) | 2005-06-08 |
DK1562902T3 (da) | 2006-08-14 |
MY137133A (en) | 2008-12-31 |
DE60305061T2 (de) | 2006-12-07 |
PT1562902E (pt) | 2006-08-31 |
US20060035938A1 (en) | 2006-02-16 |
JP2006513261A (ja) | 2006-04-20 |
HK1079200A1 (en) | 2006-03-31 |
RU2005113168A (ru) | 2006-01-20 |
PL376957A1 (pl) | 2006-01-09 |
WO2004043924A1 (en) | 2004-05-27 |
DE60305061D1 (de) | 2006-06-08 |
EP1562902B1 (en) | 2006-05-03 |
TW200500341A (en) | 2005-01-01 |
AU2003276802A1 (en) | 2004-06-03 |
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