KR970001344A - α-아드레날린수용체 길항물질로서의 피리미딘디온, 피리미딘트리온, 트리아진디온, 테트라히드로퀴나졸린디온 유도체 - Google Patents
α-아드레날린수용체 길항물질로서의 피리미딘디온, 피리미딘트리온, 트리아진디온, 테트라히드로퀴나졸린디온 유도체 Download PDFInfo
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- KR970001344A KR970001344A KR1019960020447A KR19960020447A KR970001344A KR 970001344 A KR970001344 A KR 970001344A KR 1019960020447 A KR1019960020447 A KR 1019960020447A KR 19960020447 A KR19960020447 A KR 19960020447A KR 970001344 A KR970001344 A KR 970001344A
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Abstract
본 발명은 하기 일반식(Ⅰ)의 신규한 α1-아드레날린수용체 길항물질, 및 그의 제약학상 허용되는 염 및 N-옥사이드에 관한 것이다;
(I)
상기 식 중, R1은 아세틸아미노, 아미노, 시아노, 트리플루오로아세틸아미노, 할로, 히드로, 히드록시, 니트로, 메틸술포닐아미노, 2-프로피닐옥시, 임의로 1내지 3개의 할로 원자로 추가로 치환될 수 있는, (C1-6)알킬, (C3-6)시클로알킬, (C3-6)시클로알킬(C1-4)알킬, (C1-6)알킬옥시, (C3-6)시클로알킬옥시, (C3-6)시클로알킬, (C1-4)알킬옥시 및 (C1-4)알킬티오로부터 선택되는기, 또는 아릴, 아릴(C1-4)알킬, 헤테로아릴, 헤테로아릴(C1-4)알킬, 아릴옥시, 아릴(C1-4)알킬옥시 헤테로아릴옥시 및 헤테로아릴(C1-4)알킬옥시로부터 선택되는기(여기서 아릴 및 헤테로아릴은 임의로 할로 및 시아노로부터 독립적으로 선택되는 1 내지 2개의 라디칼로 추가로 치환될 수 있음)이고; R2는 시아노, 할로 , 히드로 히드록시 또는 임의로 1 내지 3개의 할로겐 원자로 추가로 치환될 수 있는, (C1-6)알킬 및 (C1-6)알킬옥시로부터 선택되는 기이고 ; R3및 R4는 모두 히드로 또는 메틸이거나, 또는 함께 에틸렌이고; R5는 일반식
로부터 선택되는 기이고; X는 C(0), CH2또는 CH(OH)이고; Y는 CH2또는 CH(OH)이고; Z는N 또는 C(R9)(여기서, R9는 히드로, (C1-6)알킬 또는 히드록시임)이고; R6은 히드로, 임의로 1내지 3개의 할로 원자로 추가로 치환될 수 있는, (C1-6)알킬, (C3-6)시클로알킬, (C3-6)시클로알킬(C1-6)알킬로부터 선택되는 기이거나, 또는 아릴, 헤테로아릴, 아릴(C1-4)알킬 및 헤테로아릴 (C1-4)알킬로부터 선택되는 기(여기서 아릴 및 헤테로아릴은 임의로 치환, 시아노, (C1-6)알킬옥시, (C1-6)알킬 및 아릴로부터 선택되는 1내지 3개의 라디탈로 추가로 치환될 수 있음)이고; R7은 (C1-6)알카노일, 카르바모일, 시아노, 디(C1-6)알킬아미노, 할로, 히드로, 히드록시, 히드록시이미노메틸, (C1-6)알킬술포닐, (C1-4)알킬티오, 임의로 할로, 히드록시 또는 (C1-6)알킬옥시로부터 선택되는 1내지 3개의 라디칼로 추가로 치환될 수 있는, (C1-6)알킬, (C3-6)시클로알킬, (C1-6)알킬옥시 및 (C1-6)알킬옥시 (C1-4)알킬로부터 선택되는 기, 또는 아릴, 헤테로아릴, 아릴(C1-4)알킬 및 헤테로아릴(C1-4) 알킬로부터 선택되는 기(여기서 아릴 및 헤테로아릴은 임의로 할로, 시아노, (C1-6)알킬옥시, (C1-6)알킬 및 아릴로부터 선택된는 1 내지 3개의 라디칼로 추가로 치환될 수 있음)이거나 또는 R7및 R9가 함께 테트라메틸렌이며; R8은 각각 독립적으로 히드로, 히드록시, 메틸 또는 에틸이다.
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Claims (22)
- 하기 일반식(Ⅰ)의 화합물, 및 그의 제약학상 허용되는 염 및 N-옥사이드:(I)상기 식 중, R1은 아세틸아미노, 아미노, 시아노, 트리플루오로아세틸아미노, 할로, 히드로, 히드록시, 니트로, 메틸술포닐아미노, 2-프로피닐옥시, 임의로 1내지 3개의 할로 원자로 추가로 치환될 수 있는, (C1-6)알킬, (C3-6)시클로알킬, (C3-6)시클로알킬(C1-4)알킬, (C1-6)알킬옥시,(C3-6)시클로알킬옥시, (C3-6)시클로알킬, (C1-4)알킬옥시 및 (C1-4)알킬티오로부터 선택되는기, 또는 아릴, 아릴(C1-4)알킬, 헤테로아릴, 헤테로아릴(C1-4)알킬, 아릴옥시, 아릴(C1-4)알킬옥시 헤테로아릴옥시 및 헤테로아릴(C1-4)알킬옥시로부터 선택되는기(여기서 아릴 및 헤테로아릴은 임의로 할로 및 시아노로부터 독립적으로 선택되는 1 내지 2개의 라디칼로 추가로 치환될 수 있음)이고; R2는 시아노, 할로 , 히드로, 히드록시 또는 임의로 1 내지 3개의 할로겐 원자로 추가로 치환될 수 있는, (C1-6)알킬 및 (C1-6)알킬옥시로부터 선택되는 기이고 ; R3및 R4는 모두 히드로 또는 메틸이거나, 또는 함께 에틸렌이고; R5는 일반식로부터 선택되는 기이고; X는 C(0), CH2또는 CH(OH)이고; Y는 CH2또는 CH(OH)이고; Z는N 또는 C(R9)(여기서, R9는 히드로, (C1-6)알킬 또는 히드록시임)이고; R6은 히드로, 임의로 1내지 3개의 할로 원자로 추가로 치환될 수 있는, (C1-6)알킬, (C3-6)시클로알킬, (C3-6)시클로알킬(C1-4)알킬로부터 선택되는 기이거나, 또는 아릴, 헤테로아릴, 아릴(C1-4)알킬 및 헤테로아릴 (C1-4)알킬로부터 선택되는 기(여기서 아릴 및 헤테로아릴은 임의로 치환, 시아노, (C1-6)알킬옥시, (C1-6)알킬 및 아릴로부터 선택되는 1내지 3개의 라디탈로 추가로 치환될 수 있음)이고; R7은 (C1-6)알카노일, 카르바모일, 시아노, 디(C1-6)알킬아미노, 할로, 히드로, 히드록시, 히드록시이미노메틸, (C1-6)알킬술포닐, (C1-4)알킬티오, 임의로 할로, 히드록시 또는 (C1-6)알킬옥시로부터 선택되는 1내지 3개의 라디칼로 추가로 치환될 수 있는, (C1-6)알킬, (C3-6)시클로알킬, (C1-6)알킬옥시 및 (C1-6)알킬옥시 (C1-4)알킬로부터 선택되는 기, 또는 아릴, 헤테로아릴, 아릴(C1-4)알킬 및 헤테로아릴(C1-4) 알킬로부터 선택되는 기(여기서 아릴 및 헤테로아릴은 임의로 할로, 시아노, (C1-6)알킬옥시, (C1-6)알킬 및 아릴로부터 선택되는 1 내지 3개의 라디칼로 추가로 치환될 수 있음)이거나 또는 R7및 R9가 함께 테트라메틸렌이며; R8은 각각 독립적으로 히드로, 히드록시, 메틸 또는 에틸이다.
- 제1항에 있어서, R1이 임의로 1 내지 3개의 불소 원자로 추가로 치환될 수 있는 (C1-6)알킬옥시, 또는 헤테로아릴이고; R2가 히드로, 할로, 히드록시 또는 (C1-6)알킬이고; R5가 일반식(a), (b) 및 (c)로부터 선택되는 기이고, 이때 R6이 히드로, (C1-6)알킬, (C3-6)시클로알킬(C1-4)알킬, 헤테로아릴(C1-4)알킬, 또는 임의로 할로, (C1-6)알킬옥시, (C1-6)알킬 및 아릴로부터 선택되는 1 내지 3개의 라디칼로 추가로 치환될 수 있는, 벤질 및 페닐로부터 선택되는 기이고, R7이 카르바모일, 시아노, 할로, 히드로, 히드록시이미노메틸, 히드록시메틸, 또는 알킬기가 임의로 1 내지 3개의 불소 원자로 추가로 치환될 수 있는 (C1-6)알킬이거나, 또는 R7및 R9가 함께 테트라메틸렌인 화합물.
- 제2항에 있어서, R1이 메톡시, 에톡시, 2,2,2-트리플루오로에톡시, 옥사졸릴 또는 피롤릴이고; R2가 히드로, 클로로, 플루오로, 히드록시 또는 메틸이고; R6이 히드로, 메틸 시클로헥실메틸, 피리딜메틸, 피라지닐메틸, 푸릴메틸, 티에닐메틸, 비페닐메틸, 또는 임의로 클로로, 플루오로, 메틸 또는 메톡시로부터 선택되는 1 내지 3개의 라디칼로 추가로 치환될 수 있는, 벤질 및 페닐로부터 선택된 기이고; R7이 카르바모일, 시아노, 할로, 히드로, 히드록시이미노메틸, 히드록시메틸, 메틸 에틸, 프로필, 트리플루오로메틸이거나, 또는 R7및 R9가 함께 테트라메틸렌이고; X가 CH2이고 R8라디칼이 각각 히드로이거나, 또는 X가 CH(OH)이고 R8라디칼 중의 1개가 히드록시인 화합물.
- 제3항에 있어서, R1이 2,2,2-트리플루오로에톡시이고; R3및 R4가 각각 히드로이고; R5가 일반식(a)의 기(이때, R7은 히드로, 히드록시메틸 또는 메틸이고, Z는 C(R9)이고, R9는 히드로 또는 메틸 메틸임)이거나, 또는 일반식(c)의 기 (이때, X는 CH(OH)이고 R8라디칼 중의 1개는 히드록시이고 나머지는 메틸임)인 화합물.
- 제4항에 있어서, R1이 2,2,2-트리플루오로에톡시이고, Z가 CH이고, R2가 히드로이고, R6이 히드로이고, R7이 메틸인, 즉,3-(3-{4-[2-(2,2,2-트리플루오로에톡시)페닐]피레라진-1-일}프로필)-5-메틸-2,4(1H,3H)-피리미딘디온인 화합물 및 그의 제약학상 허용되는 염.
- 제5항에 있어서, 3-(3-{4-[2-(2,2,2-트리플루오로에톡시)페닐]피레라진-1-일}프로필)-5-메틸-2,4(1H,3H)-피리미딘디온 염산염인 화합물.
- 제4항에 있어서, R1이 2,2,2-트리플루오로에톡시이고, Z가 CH이고, R2가 4-위치의 플루오로이고, R6이 히드로이고, R7이 메틸인, 즉, 3-(3-{4-[4-플루오로-2--(2,2,2-트리플루오로에톡시)페닐]피페라진-1-일}프로필)--5-메틸-2,4(1H,3H)-피리미딘디온인 화합물 및 그의 제약학상 허용되는 염.
- 제7항에 있어서, 3-(3-{4-[4-플루오로-2--(2,2,2-트리플루오로에톡시)페닐]피페라진-1-일}프로필)--5-메틸-2,4(1H,3H)-피리미딘디온 푸마레이트인 화합물.
- 제4항에 있어서 R1이 2,2,2-트리플루오로에톡시이고, Z가 CH이고, R2가 4-위치의 플루오로이고, R6이 히드로이고, R7이 에틸인, 즉, 3-(3-{4-[4-플루오로-2--(2,2,2-트리플루오로에톡시)페닐]피페라진-1-일}프로필)-5-에틸-2,4(1H,3H)-피리미딘디온인 화합물 및 그의 제약학상 허용되는 염.
- 제9항에 있어서, 3-(3-{4-[4-플루오로-2-(2,2,2-트리플루오로에톡시)페닐]피페라진-1-일}프로필)-5-에틸-2,4(1H,3H)-피리미딘디온 염산염인 화합물.
- 제4항에 있어서, R1이 옥사졸-2-일이고, Z가 CH이고, R2가 4-위치의 플루오로이고, R6이 히드로이고, R7이 메틸인, 즉, 3-(3-{4-[4-플루오로-2-옥사졸-2-일페닐)피페라진-1-일]프로필}--5-메틸-2,4(1H,3H)-피리미딘디온인 화합물 및 그의 제약학상 허용되는 염.
- 제11항에 있어서, 3-(3-{4-[4-플루오로-2-옥사졸-2-일페닐)피페라진-1-일]프로필}--5-메틸-2,4(1H,3H)-피리미딘디온 옥살레이트인 화합물.
- 제4항에 있어서, R1이 2,2,2-트리플루오로에톡시이고, Z가 CH이고, R2가 4-위치의 플루오로이고, R6이 히드로이고, R7이 히드록시메틸인, 즉, 3-(3-{4-[4-플루오로-2--(2,2,2-트리플루오로에톡시)페닐]피페라진-1-일}프로필)-5-히드록시메틸-2,4(1H,3H)-피리미딘디온인 화합물 및 그의 제약학상 허용되는 염.
- 제13항에 있어서, 3-(3-{4-[4-플루오로-2--(2,2,2-트리플루오로에톡시)페닐]피페라진-1-일}프로필)-5-히드록시메틸-2,4(1H,3H)-피리미딘디온푸마레이트인 화합물.
- 제4항에 있어서, 제4항에 있어서, R1이 2,2,2-트리플루오로에톡시이고, R2가 4-위치의 플루오로이고; R3및 R4가 각각 히드로이고; R5가 일반식(c)의 기이고, 이때 X가 CH(OH)이고 R8라디칼 중의 1개가 히드록시이고 나머지는 메틸인, 즉, 시스-3-(3-{4-[4-플루오로--2-(2,2,2-트리플루오로에톡시)페닐]피페라진-1-일}프로필)-5,6-디히드록시-5-메틸-5,6-디히드로-2,4(1H,3H)-피리미딘디온인 화합물 및 그의 제약학상 허용되는 염.
- 제15항에 있어서, 시스-3-(3-{4-[4-플루오로--2-(2,2,2-트리플루오로에톡시)페닐]피페라진-1-일}프로필)-5,6-디히드록시-5-메틸-5,6-디히드로-2,4(1H,3H)-피리미딘디온 푸마레이트의(+)-거울상이성질체인 화합물.
- 제15항에 있어서, 시스-3-(3-{4-[4-플루오로--2-(2,2,2-트리플루오로에톡시)페닐]피페라진-1-일}프로필)-5,6-디히드록시-5-메틸-5,6-디히드로-2,4(1H,3H)-피리미딘디온 푸마레이트의(-)-거울상이성질체인 화합물.
- 치료 유효량의 제1항 내지 제17항 중 어느 한 항에 따른 화합물 및 제약학상 허용되는 부형제를 포함하는 약학 조성물.
- (a) 하기 일반식 3의 화합물 또는 그의 보호된 유도체를 하기 일반식 2의 화합물 또는 그의 보호된 유도체로 알킬화시킨 다음 필요에 따라 보호기제거하는 단계; 또는 (b) 식 H-R5의 화합물을 하기 일반식 5의 화합물로 알킬화시키는 단계; 및 (c)임의로 R6이 벤질인 일반식 Ⅰ의 화합물을 추가로 탈벤질화시켜 R6이 히드로인 일반식 Ⅰ의 화합물을 얻는 단계; (d) 임의로 R6이 히드로인 일반식 Ⅰ의 화합물을 추가로 알칼화시켜 R6이 (C1-6)알킬, (C3-6)시클로알킬, (C3-6)시클로알킬 (C1-4)알킬, 또는 아릴, 헤테로아릴, 아릴 (C1-4)알킬 및 헤테로아릴 (C1-4)알킬로부터 선택되는 기 (여기서 아릴 및 헤테로아릴은 임의로 할로, 시아노, (C1-6)알킬옥시, (C1-6)알킬 및 아릴로부터 선택되는 1 내지 3개의 라디칼로 추가로 치환될 수 있음)인 일반식 Ⅰ의 화합물을 얻는 단계; (e) 임의로 일반식 Ⅰ의 화합물을 추가로 산화시켜 N-옥사이드 유도체를 얻는 단계; (f) 임의로 일반식Ⅰ의 화합물의 N-옥사이드 유도체를 산화되지 않은 형태로 추가로 환원시키는 단계; (g) 임의로 일반식 Ⅰ의 화합물을 제약학상 허용되는 염으로 추가로 전환시키는 단계; 및 (h) 임의로 일반식 I의 화합물의 염 형태를 비염 형태로 추가로 전환시키는 단계를 포함하는, 하기 일반식(Ⅰ)의 화합물 및 그의 제약학상 허용되는 염 및 N-옥사이드의 제조 방법;상기 식 중, R1. R2. R3. R4및 R5는 각각 제1항에 정의한 바와 같고, L은 이탈기이다.
- 제19항에 따른 방법에 따라서 또는 그의 명백한 화학적 등가물에 의해 제조된 제1항 내지 제17항 중 어느 한 항에 따른 화합물.
- 약학활성있는 물질, 특히 양성 전립선 과형성증에 기인한 하부 요로의 폐쇄와 직간접적으로 관계있는 질병을 치료하기 위한 물질인 제1항 내지 제17항 중 어느 한 항에 따른 화합물.
- 약제, 특히 양성 전립선 과형성증에 기인한 하부 요로의 폐쇄와 직간접적으로 관계있는 질병을 치료하기 위한 약제의 제조에 사용되는, 제11항 내지 제17항 중 어느 한 항에 따른 화합물의 용도.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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KR1019960020447A KR100446877B1 (ko) | 1995-06-09 | 1996-06-08 | 알파1아드레날린수용체길항물질로서의피리미딘디온,피리미딘트리온,트리아진디온,테트라히드로퀴나졸린디온유도체 |
Country Status (32)
Country | Link |
---|---|
EP (1) | EP0748800B1 (ko) |
JP (1) | JP2721147B2 (ko) |
KR (1) | KR100446877B1 (ko) |
CN (1) | CN1118459C (ko) |
AR (1) | AR003428A1 (ko) |
AT (1) | ATE201016T1 (ko) |
AU (1) | AU710754B2 (ko) |
BR (1) | BR9602705A (ko) |
CA (1) | CA2178548A1 (ko) |
CO (1) | CO4700472A1 (ko) |
CZ (1) | CZ290004B6 (ko) |
DE (1) | DE69612698T2 (ko) |
DK (1) | DK0748800T3 (ko) |
ES (1) | ES2157366T3 (ko) |
GR (1) | GR3036307T3 (ko) |
HK (1) | HK1013065A1 (ko) |
HU (1) | HU223594B1 (ko) |
IL (1) | IL118519A (ko) |
MA (1) | MA23899A1 (ko) |
MY (1) | MY113499A (ko) |
NO (1) | NO309424B1 (ko) |
NZ (1) | NZ286720A (ko) |
PE (1) | PE46497A1 (ko) |
PL (1) | PL188061B1 (ko) |
PT (1) | PT748800E (ko) |
RU (1) | RU2175322C2 (ko) |
SA (1) | SA96170263B1 (ko) |
SG (1) | SG45486A1 (ko) |
TR (1) | TR970073A2 (ko) |
TW (1) | TW340846B (ko) |
UY (1) | UY24257A1 (ko) |
ZA (1) | ZA964561B (ko) |
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US6358959B1 (en) | 1999-01-26 | 2002-03-19 | Merck & Co., Inc. | Polyazanaphthalenone derivatives useful as alpha 1a adrenoceptor antagonists |
US6306861B1 (en) | 1999-07-30 | 2001-10-23 | Recordati S.A. Chemical And Pharmaceutical Company | Thienopyrancecarboxamide derivatives |
US6387909B1 (en) | 1999-07-30 | 2002-05-14 | Recordati S.A. Chemical And Pharmaceutical Company | Thienopyranecarboxamide derivatives |
GB2355264A (en) | 1999-09-30 | 2001-04-18 | Merck & Co Inc | Spirohydantoin derivatives useful as alpha 1a adrenoceptor antagonists |
GB2355457A (en) | 1999-09-30 | 2001-04-25 | Merck & Co Inc | Novel spirotricyclic substituted azacycloalkane derivatives useful as alpha 1a adrenoceptor antagonists |
GB2355263A (en) | 1999-09-30 | 2001-04-18 | Merck & Co Inc | Lactam and cyclic urea derivatives useful as alpha 1a adrenoceptor antagonists |
GB2355456A (en) | 1999-09-30 | 2001-04-25 | Merck & Co Inc | Novel arylhydantoin derivatives useful as alpha 1a adrenoceptor antagonists |
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US6365591B1 (en) | 1999-10-18 | 2002-04-02 | Recordati, S.A., Chemical And Pharmacueticals Company | Isoxazolecarboxamide derivatives |
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EP1339682A1 (en) * | 2000-11-30 | 2003-09-03 | Ranbaxy Laboratories, Ltd. | 1,4-disubstituted piperazine derivatives useful as uro-selective $g(a)1-adrenoceptor blockers |
MXPA04000986A (es) | 2001-08-02 | 2005-02-17 | Neurocrine Biosciences Inc | 1,2,3-triazin-3,5-dionas sustituidas como antagonistas del receptor de hormona de liberacion de gonadotropina (gnrh). |
DE10311065A1 (de) * | 2003-03-13 | 2004-09-23 | Abbott Gmbh & Co. Kg | Pyrimidin-2-on-Verbindungen und ihre therapeutische Verwendung |
US7687625B2 (en) | 2003-03-25 | 2010-03-30 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
CN1867560A (zh) | 2003-08-13 | 2006-11-22 | 武田药品工株式会社 | 4-嘧啶酮衍生物及其作为肽基肽酶抑制剂的用途 |
JP2007505121A (ja) | 2003-09-08 | 2007-03-08 | 武田薬品工業株式会社 | ジペプチジルぺプチダーゼ阻害剤 |
MY140489A (en) * | 2003-12-26 | 2009-12-31 | Eisai R&D Man Co Ltd | 1,2-di (cyclic) substituted benzene compounds |
GB0400290D0 (en) | 2004-01-08 | 2004-02-11 | Medivir Ab | dUTPase inhibitors |
CN102079743B (zh) | 2004-03-15 | 2020-08-25 | 武田药品工业株式会社 | 二肽基肽酶抑制剂 |
EP1655288A1 (en) * | 2004-11-05 | 2006-05-10 | Institut Pasteur | Aryl pyrimidyl compounds, pharmaceutical compositions comprising them, their use as antimicrobial agents |
KR101274879B1 (ko) | 2004-12-20 | 2013-06-14 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 1-시클로프로필메틸-4-[2-(3,3,5,5-테트라메틸시클로헥실)페닐]피페라진의 염 및 결정 |
WO2006068978A2 (en) | 2004-12-21 | 2006-06-29 | Takeda Pharmaceutial Company Limited | Dipeptidyl peptidase inhibitors |
WO2006126635A1 (ja) * | 2005-05-25 | 2006-11-30 | Eisai R & D Management Co., Ltd. | [2-(3,3,5,5-テトラメチルシクロヘキシル)フェニル]ピペラジン化合物の製造中間体 |
DK1942898T4 (da) | 2005-09-14 | 2014-06-02 | Takeda Pharmaceutical | Dipeptidylpeptidase-inhibitorer til behandling af diabetes |
KR101368988B1 (ko) | 2005-09-16 | 2014-02-28 | 다케다 야쿠힌 고교 가부시키가이샤 | 디펩티딜 펩티다제 억제제 |
US8324383B2 (en) | 2006-09-13 | 2012-12-04 | Takeda Pharmaceutical Company Limited | Methods of making polymorphs of benzoate salt of 2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-benzonitrile |
TW200838536A (en) | 2006-11-29 | 2008-10-01 | Takeda Pharmaceutical | Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor |
US8093236B2 (en) | 2007-03-13 | 2012-01-10 | Takeda Pharmaceuticals Company Limited | Weekly administration of dipeptidyl peptidase inhibitors |
DE102008030091B4 (de) | 2008-06-25 | 2011-03-03 | Resprotect Gmbh | Uracilderivate und deren Verwendung |
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SG193509A1 (en) * | 2011-03-18 | 2013-10-30 | Corcept Therapeutics Inc | Pyrimidine cyclohexyl glucocorticoid receptor modulators |
GB201318886D0 (en) * | 2013-10-25 | 2013-12-11 | Givaudan Sa | Improvements i or relating to organic compounds |
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EP4053120A4 (en) * | 2019-10-28 | 2023-11-01 | Nippon Soda Co., Ltd. | 2,6-DIOXO-3,6-DIHYDROPYRIMIDINE COMPOUND, BACTERICIDE FOR AGRICULTURE AND HORTICULTURE, NEMATICIDE AND ANTIFUNGAL AGENT FOR MEDICINE AND VETERINARY MEDICINE |
JPWO2022230804A1 (ko) * | 2021-04-28 | 2022-11-03 |
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DE2727469A1 (de) * | 1977-06-18 | 1978-12-21 | Hoechst Ag | Neue hexahydropyrimidine, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten |
JPH02184667A (ja) * | 1989-01-11 | 1990-07-19 | Meiji Seika Kaisha Ltd | N,n’―ジ置換ピペラジル誘導体及びそれを有効成分とする排尿障害改善剤 |
JPH0344379A (ja) * | 1989-07-13 | 1991-02-26 | Yamasa Shoyu Co Ltd | N↑3―ピペラジノウラシル誘導体 |
JP2814600B2 (ja) * | 1989-08-31 | 1998-10-22 | 正幸 石川 | 排尿障害治療剤 |
SG65570A1 (en) * | 1992-02-25 | 1999-06-22 | Recordati Chem Pharm | Heterobicyclic compounds |
FR2727682A1 (fr) * | 1994-12-02 | 1996-06-07 | Pf Medicament | Nouveaux derives de 3,5-dioxo-(2h,4h)-1,2,4-triazines, leur preparation et leur application a titre de medicament |
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1996
- 1996-05-28 ES ES96108493T patent/ES2157366T3/es not_active Expired - Lifetime
- 1996-05-28 AT AT96108493T patent/ATE201016T1/de not_active IP Right Cessation
- 1996-05-28 EP EP96108493A patent/EP0748800B1/en not_active Expired - Lifetime
- 1996-05-28 DK DK96108493T patent/DK0748800T3/da active
- 1996-05-28 PT PT96108493T patent/PT748800E/pt unknown
- 1996-05-28 DE DE69612698T patent/DE69612698T2/de not_active Expired - Fee Related
- 1996-05-31 IL IL11851996A patent/IL118519A/xx not_active IP Right Cessation
- 1996-06-03 AU AU54690/96A patent/AU710754B2/en not_active Ceased
- 1996-06-03 ZA ZA964561A patent/ZA964561B/xx unknown
- 1996-06-04 NZ NZ286720A patent/NZ286720A/en unknown
- 1996-06-05 HU HU9601529A patent/HU223594B1/hu not_active IP Right Cessation
- 1996-06-05 PL PL96314635A patent/PL188061B1/pl not_active IP Right Cessation
- 1996-06-06 TR TR96/00475A patent/TR970073A2/xx unknown
- 1996-06-06 AR ARP960103000A patent/AR003428A1/es active IP Right Grant
- 1996-06-06 MA MA24270A patent/MA23899A1/fr unknown
- 1996-06-06 PE PE1996000428A patent/PE46497A1/es not_active Application Discontinuation
- 1996-06-07 UY UY24257A patent/UY24257A1/es not_active IP Right Cessation
- 1996-06-07 CA CA002178548A patent/CA2178548A1/en not_active Abandoned
- 1996-06-07 RU RU96111418/04A patent/RU2175322C2/ru not_active IP Right Cessation
- 1996-06-07 BR BR9602705A patent/BR9602705A/pt not_active IP Right Cessation
- 1996-06-07 NO NO962412A patent/NO309424B1/no unknown
- 1996-06-07 CO CO96029677A patent/CO4700472A1/es unknown
- 1996-06-07 CN CN96110490A patent/CN1118459C/zh not_active Expired - Fee Related
- 1996-06-07 MY MYPI96002314A patent/MY113499A/en unknown
- 1996-06-07 SG SG1996010018A patent/SG45486A1/en unknown
- 1996-06-07 JP JP8145236A patent/JP2721147B2/ja not_active Expired - Fee Related
- 1996-06-08 KR KR1019960020447A patent/KR100446877B1/ko not_active IP Right Cessation
- 1996-06-10 CZ CZ19961696A patent/CZ290004B6/cs not_active IP Right Cessation
- 1996-07-11 TW TW085108416A patent/TW340846B/zh active
- 1996-08-26 SA SA96170263A patent/SA96170263B1/ar unknown
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1998
- 1998-12-21 HK HK98114167A patent/HK1013065A1/xx not_active IP Right Cessation
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