KR940702868A - 포스포디에스터라제 ⅳ 억제 활성을 갖는 벤조 및 피리도 피리다지논 및 피리다진티온 화합물 - Google Patents

포스포디에스터라제 ⅳ 억제 활성을 갖는 벤조 및 피리도 피리다지논 및 피리다진티온 화합물

Info

Publication number
KR940702868A
KR940702868A KR1019940701129A KR19940701129A KR940702868A KR 940702868 A KR940702868 A KR 940702868A KR 1019940701129 A KR1019940701129 A KR 1019940701129A KR 19940701129 A KR19940701129 A KR 19940701129A KR 940702868 A KR940702868 A KR 940702868A
Authority
KR
South Korea
Prior art keywords
compound
hydrogen
lower alkyl
formula
nitro
Prior art date
Application number
KR1019940701129A
Other languages
English (en)
Other versions
KR100263494B1 (ko
Inventor
스티븐 윌헬름 로버트
얼 로우 브레들리
헨리 디벤스 브루스
알바레쯔 로버트
그랜트 마틴 마이클
Original Assignee
헤르비크 폰 모르제
신텍스(유.에스.에이.)인코포레이티드(Syntex(U.S.A.)Inc.)
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by 헤르비크 폰 모르제, 신텍스(유.에스.에이.)인코포레이티드(Syntex(U.S.A.)Inc.) filed Critical 헤르비크 폰 모르제
Publication of KR940702868A publication Critical patent/KR940702868A/ko
Application granted granted Critical
Publication of KR100263494B1 publication Critical patent/KR100263494B1/ko

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
    • C07D237/30—Phthalazines
    • C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Pulmonology (AREA)
  • Pain & Pain Management (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Rheumatology (AREA)
  • Transplantation (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

일반식(Ⅰ)의 벤조 또는 피리도피리다지논 및 피리다진티온 또는 이의 약제학적으로 허용되는 에스테르, 에테르 또는 염이 항염증제, 항천식제, 면역억제제, 항이인자형이식 거부반응, 항-이식-대-숙주 거부반응, 자기 면역 질환 또는 진통제(들)로서 유용하다는 것을 발견했다.
상기식에서, X 및 Y는 질소 또는 탄소 원자이며, 단 이들중 적어도 하나는 탄소이고 Z는 산소 또는 황이며; R1은 수소, 저급 알킬, 아릴, 헤테로아릴, 또는 헤테로사이클 저급 알킬렌이고; R2, R3, R4, R5및 R6은 독립적으로 수소, 저급 알킬, 할로, 카복시, 알콕시카보닐, 카바모일, 아실, 아실할라이드, 티오메틸, 트리플루오로메틸, 시아노 또는 니트로이다.

Description

포스포디에스터라제 Ⅳ 억제 활성을 갖는 벤조 및 피리도 피리다지논 및 피리다진티온 화합물
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (33)

  1. 일반식(Ⅰ)의 화합물 또는 이의 약제학적으로 허용되는 에스테르, 에테르 또는 염.
    상기식에서, X 및 Y는 질소 또는 탄소 원자이며, 단 이들중 적어도 하나는 탄소이고 Z는 산소 또는 황이며; R1은 수소, 저급 알킬, 아릴, 헤테로아릴, 또는 헤테로사이클 저급 알킬렌이고; R2, R3, R4, R5및 R6은 독립적으로 수소, 저급 알킬, 할로, 카복시, 알콕시카보닐, 카바모일, 아실, 아실할라이드, 티오메틸, 트리플루오로메틸, 시아노 또는 니트로이다.
  2. 제1항에 있어서, X는 질소이고, Y는 탄소이며 Z는 산소인 화합물.
  3. 제2항에 있어서, R2, R4, R5및 R6이 수소이고, R3가 할로인 화합물.
  4. 제3항에 있어서, R1이 저급 알킬, 아릴, 또는 헤테로사이클 저급 알킬렌인 화합물.
  5. 제4항에 있어서, R1이 에틸, 2-프로필, 사이클로프로필메틸 또는 사이클로펜틸메틸인 화합물.
  6. 제4항에 있어서, R1이 벤질인 화합물.
  7. 제4항에 있어서, R1이 4-피리딜메틸, 4-피리딜-N-옥사이드-메틸, 3-피리딜메틸, 3-피리딜-N-옥사이드-메틸, 또는 3-피리딜메틸인 화합물.
  8. 제2항에 있어서, R2, R4, R5및 R6이 수소이고 R3가 니트로인 화합물.
  9. 제8항에 있어서, R1이 저급 알킬, 아릴, 또는 헤테로사이클 저급 알킬렌인 화합물.
  10. 제9항에 있어서, R1이 에틸, 2-프로필, 사이클로프로필메틸 또는 사이클로펜틸메틸인 화합물.
  11. 제9항에 있어서, R1이 벤질인 화합물.
  12. 제9항에 있어서, R1이 4-피리딜메틸, 4-피리딜-N-옥사이드-메틸, 3-피리딜메틸, 3-피리딜-N-옥사이드-메틸, 또는 3-티에닐메틸인 화합물.
  13. 제2항에 있어서, R2, R3, R4, R5및 R6이 수소인 화합물.
  14. 제1항에 있어서, X는 탄소이고, Y는 질소이며 Z는 산소인 화합물.
  15. 제14항에 있어서, R2, R4, R5및 R6이 수소이고 R3가 할로 또는 니트로인 화합물.
  16. 제15항에 있어서, R1이 저급 알킬, 아릴, 또는 헤테로 사이클 저급 알킬렌인 화합물.
  17. 제14항에 있어서, R2, R3, R4, R5및 R6이 수소인 화합물.
  18. 제1항에 있어서, X는 탄소이고, Y는 탄소이며 Z는 산소인 화합물.
  19. 제18항에 있어서, R2, R4, R5및 R6이 수소이고 R3가 할로 또는 니트로인 화합물.
  20. 제19항에 있어서, R1이 저급 알킬, 아릴, 또는 헤테로 사이클 저급 알킬렌인 화합물.
  21. 제18항에 있어서, R2, R3, R4, R5및 R6이 수소인 화합물.
  22. 제1항에 있어서, X는 질소이고, Y는 탄소이며 Z는 황인 화합물.
  23. 제22항에 있어서, R2, R4, R5및 R6이 수소이고 R3가 할로 또는 니트로인 화합물.
  24. 제23항에 있어서, R1이 저급 알킬, 아릴, 또는 헤테로사이클 저급 알킬렌인 화합물.
  25. 제22항에 있어서, R2, R3, R4, R5및 R6이 수소인 화합물.
  26. 일반식(Ⅱ)의 화합물 또는 이의 약제학적으로 허용되는 에스테르, 에테르 또는 염.
    상기식에서, X 및 Y는 질소 또는 탄소원자이며, 단 이들중 적어도 하나는 탄소이고, R2, R3, R5및 R6은 독립적으로 수소, 저급 알킬, 할로, 카복시, 알콕시카보닐, 카바모일, 아실, 아실할라이드, 티오메틸, 트리플루오로메틸, 시아노 또는 니트로이며, R4는 수소, 저급 알킬, 요오도, 브로모, 클로로, 카복시, 에스테르, 카바모일, 아실, 아실 할라이드 또는 니트로이고; R7은 저급 알킬이다.
  27. 제26항에 있어서, R3은 할로 또는 니트로인 화합물.
  28. 제26항에 있어서, R2, R3, R4, R5및 R6은 수소인 화합물.
  29. 치료학적 유효량의 일반식(Ⅰ)의 화합물, 또는 이의 약제학적으로 허용되는 에스테르, 에테르 또는 염 및 약제학적으로 허용되는 부형제를 포함하는 약제학적 조성물.
    상기식에서, X 및 Y는 질소 또는 탄소 원자이며, 단 이들중 적어도 하나는 탄소이고 Z는 산소 또는 황이며; R1은 수소, 저급 알킬, 아릴, 헤테로아릴, 또는 헤테로사이클저급 알킬렌이고; R2, R3, R4, R5및 R6은 독립적으로 수소, 저급 알킬, 할로, 카복시, 알콕시카보닐, 카바모일, 아실, 아실할라이드, 티오메틸, 트리플루오로메틸, 시아노 또는 니트로이다.
  30. 치료학적 유효량의 제1항 내지 제25항중 어느 한 항에 따른 화합물을 바람직하게는 하나 이상의 약제학적으로 허용되는 부형제와의 배합물로서 포함하는 약제학적 조성물.
  31. 포유동물의 천식, 통증, 염증 질환, 이인자형이식(allograft) 거부반응, 이식-대-숙주-거부반응, 및 자가면역질환을 치료하기 위한 약제를 제조하기 위한 일반식(Ⅰ)의 화합물 또는 이의 약제학적으로 허용되는 에스케르, 에테르 또는 염의 용도.
    상기식에서, X 및 Y는 질소 또는 탄소 원자이며, 단 이들중 적어도 하나는 탄소이고 Z는 산소 또는 황이며; R1은 수소, 저급 알킬, 아릴, 헤테로아릴, 또는 헤테로사이클 저급 알킬렌이고, R2, R3, R4, R5및 R6은 독립적으로 수소, 저급 알킬, 할로, 카복시, 알콕시카보닐, 카바모일, 아실, 아실할라이드, 티오메틸, 트리플루오로메틸, 시아노 또는 니트로이다.
  32. a)일반식(Ⅱ)의 화합물과 일반식(Ⅲ)의 화합물을 반응시키거나; b)일반식(Ⅰ)의 화합물을 일반식(Ⅰ)의 약제학적으로 허용되는 염으로 전환시키거나; 또는 c)일반식(Ⅰ)의 화합물의 염을 일반식(Ⅰ)의 상응하는 유기 염기 또는 다른 약제학적으로 허용되는 염으로 전환시킴을 특징으로 하여 일반식(Ⅰ)이 화합물 또는 이의 약제학적으로 허용되는 염을 제조하는 방법.
    (Ⅲ)
    상기식에서, X 및 Y는 질소 또는 원자이며, 단 이들중 적어도 하나는 탄소이고, Z는 산소이며; R1은 수소, 저급 알킬, 아릴, 헤테로아릴, 또는 헤테로사이클 저급 알킬렌이고; R2, R3, R4, R5및 R6은 독립적으로 수소, 저급 알킬, 할로, 카복시, 알콕시카보닐, 카바모일, 아실, 아실 할라이드, 티오메틸, 트리플루오로메틸, 시아노 또는 니트로이며, 단 일반식(Ⅱ)에 있어서, R4는 수소, 저급 알킬, 요오도, 브로모, 클로로, 카복시, 에스테르, 카바모일, 아실, 아실 할라이드, 티오메틸, 트리플루오로메틸, 시아노, 또는 니트로이고; R7은 저급 알킬이다.
  33. 제32항에 있어서, Z가 산소인 일반식(Ⅰ)의 화합물을 티에이트화제와 반응시켜 Z가 황인 일반식(Ⅰ)의 화합물을 제조하는 단계를 추가로 포함하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019940701129A 1991-10-09 1992-10-08 피리도피리다지논 및 피리다진티온 화합물 KR100263494B1 (ko)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US77567991A 1991-10-09 1991-10-09
US07/775,679 1991-10-09
US7/775.679 1991-10-09
PCT/US1992/008398 WO1993007146A1 (en) 1991-10-09 1992-10-08 Benzo and pyrido pyridazinone and pyridazinthione compounds with pde iv inhibiting activity

Publications (2)

Publication Number Publication Date
KR940702868A true KR940702868A (ko) 1994-09-17
KR100263494B1 KR100263494B1 (ko) 2000-08-01

Family

ID=25105161

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019940701129A KR100263494B1 (ko) 1991-10-09 1992-10-08 피리도피리다지논 및 피리다진티온 화합물

Country Status (20)

Country Link
EP (1) EP0612321B1 (ko)
JP (1) JP3245165B2 (ko)
KR (1) KR100263494B1 (ko)
AT (1) ATE183745T1 (ko)
AU (1) AU670544B2 (ko)
CA (1) CA2117059C (ko)
DE (1) DE69229874T2 (ko)
DK (1) DK0612321T3 (ko)
ES (2) ES2105920B1 (ko)
FI (1) FI108229B (ko)
GR (1) GR3030969T3 (ko)
HU (2) HUT66969A (ko)
IL (1) IL103388A (ko)
MX (1) MX9205794A (ko)
NO (1) NO302888B1 (ko)
NZ (1) NZ244660A (ko)
PT (1) PT100938B (ko)
TW (1) TW365606B (ko)
WO (1) WO1993007146A1 (ko)
ZA (1) ZA927755B (ko)

Families Citing this family (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9200689D0 (en) * 1992-01-14 1992-03-11 Rhone Poulenc Agriculture New compositions of matter
GB9314412D0 (en) * 1993-07-13 1993-08-25 Rhone Poulenc Agriculture New compositions of matter
US5665754A (en) * 1993-09-20 1997-09-09 Glaxo Wellcome Inc. Substituted pyrrolidines
US5466697A (en) * 1994-07-13 1995-11-14 Syntex (U.S.A.) Inc. 8-phenyl-1,6-naphthyridin-5-ones
NZ291507A (en) * 1994-08-29 1997-12-19 Yamanouchi Pharma Co Ltd 1,8-naphthyridine derivatives; medicaments
GB9712761D0 (en) * 1997-06-17 1997-08-20 Chiroscience Ltd Quinolines and their therapeutic use
US6069151A (en) * 1996-11-06 2000-05-30 Darwin Discovery, Ltd. Quinolines and their therapeutic use
ES2137113B1 (es) * 1997-07-29 2000-09-16 Almirall Prodesfarma Sa Nuevos derivados de triazolo-piridazinas heterociclicos.
DE69821530T2 (de) 1997-12-15 2004-12-23 Altana Pharma Ag Dihydrobenzifurane
EP0934933A1 (en) * 1998-02-06 1999-08-11 Byk Gulden Lomberg Chemische Fabrik GmbH Phthalazinones
IT1303272B1 (it) 1998-10-29 2000-11-06 Zambon Spa Derivati triciclici inibitori della fosfodiesterasi 4
UA71945C2 (en) * 1999-01-27 2005-01-17 Pfizer Prod Inc Substituted bicyclic derivatives being used as anticancer agents
JP3270834B2 (ja) 1999-01-27 2002-04-02 ファイザー・プロダクツ・インク 抗がん剤として有用なヘテロ芳香族二環式誘導体
CA2381802C (en) 1999-08-21 2010-12-07 Byk Gulden Lomberg Chemische Fabrik Gmbh Synergistic combination of roflumilast and salmeterol
EE05386B1 (et) * 2001-02-15 2011-02-15 ALTANA�Pharma�AG Ftalasinoon-piperidinoderivaadid,ÁnendeÁkasutamineÁjaÁravim
IL157870A0 (en) 2001-04-25 2004-03-28 Altana Pharma Ag Piperazino derivatives and pharmaceutical compositions containing the same
JP2004526789A (ja) * 2001-04-25 2004-09-02 アルタナ　ファルマ　アクチエンゲゼルシャフト 新規フタラジノン
ES2195785B1 (es) 2002-05-16 2005-03-16 Almirall Prodesfarma, S.A. Nuevos derivados de piridazin-3(2h)-ona.
PL372926A1 (en) 2002-08-10 2005-08-08 Altana Pharma Ag Piperidine-pyridazones and phthalazones as pde4 inhibitors
PL373597A1 (en) * 2002-08-10 2005-09-05 Altana Pharma Ag Piperidine-n-oxide-derivatives
ES2211344B1 (es) * 2002-12-26 2005-10-01 Almirall Prodesfarma, S.A. Nuevos derivados de piridazin-3(2h)-ona.
US7772188B2 (en) 2003-01-28 2010-08-10 Ironwood Pharmaceuticals, Inc. Methods and compositions for the treatment of gastrointestinal disorders
EA200501548A1 (ru) 2003-04-01 2006-02-24 Апплайд Резеч Системз Арс Холдинг Н.В. Ингибиторы фосфодиэстераз при бесплодии
DE602005005638T2 (de) 2004-02-04 2009-05-14 Nycomed Gmbh 2-(piperidin-4-yl)-4,5-dihydro-2h-pyridazin-3-on-derivate als pde4-inhibitoren
ES2251866B1 (es) 2004-06-18 2007-06-16 Laboratorios Almirall S.A. Nuevos derivados de piridazin-3(2h)-ona.
US8969514B2 (en) 2007-06-04 2015-03-03 Synergy Pharmaceuticals, Inc. Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases
EP2170930B3 (en) 2007-06-04 2013-10-02 Synergy Pharmaceuticals Inc. Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders
PL383550A1 (pl) * 2007-10-15 2009-04-27 Uniwersytet Łódzki Nowe pochodne benzeno- i pirydopirydazynonów
JP2011522828A (ja) 2008-06-04 2011-08-04 シナジー ファーマシューティカルズ インコーポレイテッド 胃腸障害、炎症、癌、およびその他の障害の治療のために有用なグアニル酸シクラーゼのアゴニスト
AU2009270833B2 (en) 2008-07-16 2015-02-19 Bausch Health Ireland Limited Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders
US9616097B2 (en) 2010-09-15 2017-04-11 Synergy Pharmaceuticals, Inc. Formulations of guanylate cyclase C agonists and methods of use
DK2681236T3 (en) 2011-03-01 2018-04-16 Synergy Pharmaceuticals Inc PROCEDURE FOR MANUFACTURING GUANYLATE CYCLASE-C-AGONISTS
US20130116241A1 (en) * 2011-11-09 2013-05-09 Abbvie Inc. Novel inhibitor compounds of phosphodiesterase type 10a
WO2013097052A1 (en) 2011-12-30 2013-07-04 Abbott Laboratories Bromodomain inhibitors
EP2958577A2 (en) 2013-02-25 2015-12-30 Synergy Pharmaceuticals Inc. Guanylate cyclase receptor agonists for use in colonic cleansing
MX365950B (es) 2013-03-13 2019-06-19 Flatley Discovery Lab Llc Compuestos de piridazinona y metodos para el tratamiento de la fibrosis quistica.
CA2905435A1 (en) 2013-03-15 2014-09-25 Synergy Pharmaceuticals Inc. Compositions useful for the treatment of gastrointestinal disorders
WO2014151206A1 (en) 2013-03-15 2014-09-25 Synergy Pharmaceuticals Inc. Agonists of guanylate cyclase and their uses
EP3004138B1 (en) 2013-06-05 2024-03-13 Bausch Health Ireland Limited Ultra-pure agonists of guanylate cyclase c, method of making and using same
AU2014305843B2 (en) 2013-08-09 2019-08-29 Ardelyx, Inc. Compounds and methods for inhibiting phosphate transport
US11319318B2 (en) * 2015-03-05 2022-05-03 Boehringer Ingelheim International Gmbh Pyridinones and isoquinolinones as inhibitors of the bromodomain BRD9
EP3428151A4 (en) 2016-03-09 2020-02-19 Nippon Soda Co., Ltd. PYRIDINE COMPOUND AND USE THEREOF
TWI764237B (zh) 2016-04-15 2022-05-11 美商艾伯維有限公司 溴域抑制劑
US20200368223A1 (en) 2019-05-21 2020-11-26 Ardelyx, Inc. Methods for inhibiting phosphate transport
FR3105254B1 (fr) 2019-12-19 2022-08-12 Syctom Lagence Metropolitaine Des Dechets Menagers Installation et procédé de gazéification hydrothermale de biomasse

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2805344B2 (ja) * 1989-07-11 1998-09-30 昭和電工株式会社 オレフィン重合触媒の製造方法およびオレフィンの重合方法
AU7238191A (en) * 1990-02-19 1991-09-03 Chugai Seiyaku Kabushiki Kaisha Novel fused heterocyclic compound and antiasthmatic agent prepared therefrom

Also Published As

Publication number Publication date
TW365606B (en) 1999-08-01
IL103388A0 (en) 1993-03-15
FI108229B (fi) 2001-12-14
PT100938B (pt) 1999-10-29
DE69229874D1 (de) 1999-09-30
EP0612321A1 (en) 1994-08-31
EP0612321B1 (en) 1999-08-25
CA2117059A1 (en) 1993-04-15
GR3030969T3 (en) 1999-11-30
AU670544B2 (en) 1996-07-25
MX9205794A (es) 1993-04-01
FI941567A (fi) 1994-04-06
WO1993007146A1 (en) 1993-04-15
HUT66969A (en) 1995-01-30
PT100938A (pt) 1993-10-29
HU210814A9 (en) 1995-08-28
DK0612321T3 (da) 1999-12-13
NO941210D0 (no) 1994-04-05
AU2781592A (en) 1993-05-03
ZA927755B (en) 1994-04-08
FI941567A0 (fi) 1994-04-06
DE69229874T2 (de) 1999-12-09
ATE183745T1 (de) 1999-09-15
NZ244660A (en) 1995-05-26
ES2105920A1 (es) 1997-10-16
JPH07500321A (ja) 1995-01-12
IL103388A (en) 1997-09-30
JP3245165B2 (ja) 2002-01-07
KR100263494B1 (ko) 2000-08-01
ES2135416T3 (es) 1999-11-01
NO941210L (no) 1994-04-05
NO302888B1 (no) 1998-05-04
HU9400949D0 (en) 1994-06-28
ES2105920B1 (es) 1998-07-01
CA2117059C (en) 2003-05-20

Similar Documents

Publication Publication Date Title
KR940702868A (ko) 포스포디에스터라제 ⅳ 억제 활성을 갖는 벤조 및 피리도 피리다지논 및 피리다진티온 화합물
NO153220C (no) Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazolinderivater.
NO153455C (no) Analogifremgangsmaate for fremstilling av terapeutisk aktive, substituerte imidazolderivater.
ES2258763T3 (es) Carbamatos de rapamicina.
NO852514L (no) Analogifremgangsmaate for fremstilling av terapeutisk aktive 8-alkyltio-2-piperazino-pyrimido (5,4-d) pyrimidin-derivater.
FI801769A (fi) Paromomycin-derivat foerfarande foer deras framstaellning och terapeutiska kompositioner daer de ingaor
PH20392A (en) Pyridobenzodiazepinones pharmaceutical compositions thereof and method of use thereof
KR920016456A (ko) 5-(치환 아미노) -1,2,4-트리아졸로 [1,5-a]피리미딘 유도체
US3795681A (en) Aminothiophene-carboxylic acid esters
NO803547L (no) Analogifremgangsmaate for fremstilling av terapeutisk aktive 2-fenylamino-imidazolin-derivater
DE69104719T2 (de) Alkoxy-substituierte dihydrobenzopyran-2-carbonsäure und deren derivate.
TW360655B (en) Heterocyclyl-ergoline derivatives
NO803748L (no) Analogifremgangsmaate for fremstilling av terapeutisk aktive fenylamino-imidazolin-derivater
KR900004730A (ko) 정신병 치료제인 4-[4-(3-벤즈이소티아졸릴)-1-피페라지닐]부틸 가교결합된 이환상 이미드
KR920000751A (ko) [(1-아릴피롤리딘-2-일)메틸]피페라진 유도체, 그들의 제법 및 치료학적 용도

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20080407

Year of fee payment: 9

LAPS Lapse due to unpaid annual fee