AU761191B2 - Therapies for tissue damage resulting from ischemia - Google Patents
Therapies for tissue damage resulting from ischemia Download PDFInfo
- Publication number
- AU761191B2 AU761191B2 AU40685/02A AU4068502A AU761191B2 AU 761191 B2 AU761191 B2 AU 761191B2 AU 40685/02 A AU40685/02 A AU 40685/02A AU 4068502 A AU4068502 A AU 4068502A AU 761191 B2 AU761191 B2 AU 761191B2
- Authority
- AU
- Australia
- Prior art keywords
- pyridazin
- benzenesulfonyl
- compound
- alkyl
- prodrug
- 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
Links
- 238000002560 therapeutic procedure Methods 0.000 title claims abstract description 19
- 208000028867 ischemia Diseases 0.000 title claims abstract description 18
- 230000000451 tissue damage Effects 0.000 title claims abstract description 9
- 231100000827 tissue damage Toxicity 0.000 title claims abstract description 9
- 241000124008 Mammalia Species 0.000 claims abstract description 14
- 230000002265 prevention Effects 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 181
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 239000000651 prodrug Substances 0.000 claims description 44
- 229940002612 prodrug Drugs 0.000 claims description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 29
- 210000001519 tissue Anatomy 0.000 claims description 27
- 210000002216 heart Anatomy 0.000 claims description 25
- 125000001624 naphthyl group Chemical group 0.000 claims description 19
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 102000016912 Aldehyde Reductase Human genes 0.000 claims description 16
- 108010053754 Aldehyde reductase Proteins 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- FAPYYQBGANAWEI-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)sulfonyl-1h-pyridazin-6-one Chemical compound ClC1=CC(Cl)=CC=C1S(=O)(=O)C1=NNC(=O)C=C1 FAPYYQBGANAWEI-UHFFFAOYSA-N 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- YIGVCMPHSHVCQW-UHFFFAOYSA-N 3-(2,3-difluorophenyl)sulfonyl-1h-pyridazin-6-one Chemical compound FC1=CC=CC(S(=O)(=O)C2=NNC(=O)C=C2)=C1F YIGVCMPHSHVCQW-UHFFFAOYSA-N 0.000 claims description 9
- HJXKXDILPXEWJY-UHFFFAOYSA-N 3-naphthalen-1-ylsulfonyl-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)C=2C3=CC=CC=C3C=CC=2)=N1 HJXKXDILPXEWJY-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- ABHDLEMQXCSODP-UHFFFAOYSA-N 3-(2-bromo-4-fluorophenyl)sulfonyl-1h-pyridazin-6-one Chemical compound BrC1=CC(F)=CC=C1S(=O)(=O)C1=NNC(=O)C=C1 ABHDLEMQXCSODP-UHFFFAOYSA-N 0.000 claims description 8
- JORLLGPOJPMFRS-UHFFFAOYSA-N 3-(3-chlorophenyl)sulfonyl-1h-pyridazin-6-one Chemical compound ClC1=CC=CC(S(=O)(=O)C2=NNC(=O)C=C2)=C1 JORLLGPOJPMFRS-UHFFFAOYSA-N 0.000 claims description 8
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 210000005003 heart tissue Anatomy 0.000 claims description 7
- AFMMZMYEGLGTBX-UHFFFAOYSA-N 3-(2-chloro-4-fluorophenyl)sulfonyl-1h-pyridazin-6-one Chemical compound ClC1=CC(F)=CC=C1S(=O)(=O)C1=NNC(=O)C=C1 AFMMZMYEGLGTBX-UHFFFAOYSA-N 0.000 claims description 6
- AEDNYZQZIZUZTP-UHFFFAOYSA-N 3-(2-fluorophenyl)sulfonyl-1h-pyridazin-6-one Chemical compound FC1=CC=CC=C1S(=O)(=O)C1=NNC(=O)C=C1 AEDNYZQZIZUZTP-UHFFFAOYSA-N 0.000 claims description 6
- WSTJUPLIBBVJLM-UHFFFAOYSA-N 3-(2,3-dichlorophenyl)sulfonyl-1h-pyridazin-6-one Chemical compound ClC1=CC=CC(S(=O)(=O)C2=NNC(=O)C=C2)=C1Cl WSTJUPLIBBVJLM-UHFFFAOYSA-N 0.000 claims description 5
- OTXVZGMQNJRLIN-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)sulfonyl-1h-pyridazin-6-one Chemical compound ClC1=CC=CC(Cl)=C1S(=O)(=O)C1=NNC(=O)C=C1 OTXVZGMQNJRLIN-UHFFFAOYSA-N 0.000 claims description 5
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- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims description 5
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- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
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- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29339301P | 2001-05-24 | 2001-05-24 | |
| US60/293393 | 2001-05-24 |
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|---|---|
| AU4068502A AU4068502A (en) | 2002-11-28 |
| AU761191B2 true AU761191B2 (en) | 2003-05-29 |
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|---|---|---|---|
| AU40685/02A Ceased AU761191B2 (en) | 2001-05-24 | 2002-05-16 | Therapies for tissue damage resulting from ischemia |
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|---|---|
| US (1) | US6872722B2 (https=) |
| EP (1) | EP1260224B1 (https=) |
| JP (1) | JP2002370984A (https=) |
| KR (1) | KR20020090321A (https=) |
| CN (1) | CN1390547A (https=) |
| AT (1) | ATE289510T1 (https=) |
| AU (1) | AU761191B2 (https=) |
| CA (1) | CA2387007A1 (https=) |
| CZ (1) | CZ20021782A3 (https=) |
| DE (1) | DE60203026T2 (https=) |
| ES (1) | ES2236447T3 (https=) |
| HU (1) | HUP0201738A3 (https=) |
| PL (1) | PL354128A1 (https=) |
| SK (1) | SK7332002A3 (https=) |
| ZA (1) | ZA200203985B (https=) |
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|---|---|---|---|---|
| EP1236720B1 (en) * | 2001-02-28 | 2005-06-15 | Pfizer Products Inc. | Sulfonyl pyridazinone compounds useful as aldose reductase inhibitors |
| DK1961420T3 (da) * | 2005-12-16 | 2012-08-27 | Sanwa Kagaku Kenkyusho Co | Middel til forebyggelse og behandling af akut nyresvigt |
| KR20080108465A (ko) * | 2006-02-20 | 2008-12-15 | 가부시키가이샤산와카가쿠켄큐쇼 | 뇌졸중에 있어서의 뇌허혈 또는 뇌허혈 재관류 장해의 예방또는 치료제 |
| WO2022197487A1 (en) | 2021-03-18 | 2022-09-22 | Banavara MYLARI | Combination of aldose reductase inhibitors and probenecid for the treatment of diabetic complications |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5670504A (en) * | 1995-02-23 | 1997-09-23 | Merck & Co. Inc. | 2,6-diaryl pyridazinones with immunosuppressant activity |
| EP1043317A1 (en) * | 1997-11-19 | 2000-10-11 | Kowa Co., Ltd. | Novel pyridazine derivatives and drugs containing the same as the active ingredient |
| EP1236720A1 (en) * | 2001-02-28 | 2002-09-04 | Pfizer Products Inc. | Sulfonyl pyridazinone compounds useful as aldose reductase inhibitors |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE47592B1 (en) | 1977-12-29 | 1984-05-02 | Ici Ltd | Enzyme inhibitory phthalazin-4-ylacetic acid derivatives, pharmaceutical compositions thereof,and process for their manufacture |
| US4939140A (en) | 1985-11-07 | 1990-07-03 | Pfizer Inc. | Heterocyclic oxophthalazinyl acetic acids |
| JPH01258671A (ja) * | 1987-12-01 | 1989-10-16 | Morishita Pharmaceut Co Ltd | ５−（１ｈ−イミダゾール−１−イル）−３（２ｈ）−ピリダジノン誘導体 |
| US4996204A (en) | 1989-05-11 | 1991-02-26 | Pfizer Inc. | Pyrido[2,3-d]pyridazinones as aldose reductase inhibitors |
| WO1992017446A2 (en) * | 1991-03-28 | 1992-10-15 | Pfizer Inc. | Pyridazinone acetic acids aldose reductase inhibitors |
| US5834466A (en) | 1994-12-22 | 1998-11-10 | The Regents Of The University Of California | Method for protecting of heart by limiting metabolic and ionic abnormalities developed during ischemia, following ischemia or resulting from ischemia |
| US5506228A (en) * | 1995-02-23 | 1996-04-09 | Merck & Co., Inc. | 2,6-diaryl pyridazinones with immunosuppressant activity |
| TWI241295B (en) * | 1998-03-02 | 2005-10-11 | Kowa Co | Pyridazine derivative and medicine containing the same as effect component |
| JP2000247959A (ja) * | 1999-02-26 | 2000-09-12 | Kowa Co | ピリダジン−３−オン誘導体及びこれを含有する医薬 |
| CA2442476A1 (en) * | 2001-03-30 | 2002-10-10 | Pfizer Products Inc. | Pyridazinone aldose reductase inhibitors |
-
2002
- 2002-05-16 AU AU40685/02A patent/AU761191B2/en not_active Ceased
- 2002-05-17 CA CA002387007A patent/CA2387007A1/en not_active Abandoned
- 2002-05-20 JP JP2002144503A patent/JP2002370984A/ja active Pending
- 2002-05-20 ZA ZA200203985A patent/ZA200203985B/xx unknown
- 2002-05-22 ES ES02253605T patent/ES2236447T3/es not_active Expired - Lifetime
- 2002-05-22 DE DE60203026T patent/DE60203026T2/de not_active Expired - Fee Related
- 2002-05-22 CZ CZ20021782A patent/CZ20021782A3/cs unknown
- 2002-05-22 EP EP02253605A patent/EP1260224B1/en not_active Expired - Lifetime
- 2002-05-22 AT AT02253605T patent/ATE289510T1/de not_active IP Right Cessation
- 2002-05-23 HU HU0201738A patent/HUP0201738A3/hu unknown
- 2002-05-23 US US10/154,694 patent/US6872722B2/en not_active Expired - Fee Related
- 2002-05-23 KR KR1020020028665A patent/KR20020090321A/ko not_active Ceased
- 2002-05-24 PL PL02354128A patent/PL354128A1/xx not_active Application Discontinuation
- 2002-05-24 SK SK733-2002A patent/SK7332002A3/sk unknown
- 2002-05-24 CN CN02120397A patent/CN1390547A/zh active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5670504A (en) * | 1995-02-23 | 1997-09-23 | Merck & Co. Inc. | 2,6-diaryl pyridazinones with immunosuppressant activity |
| EP1043317A1 (en) * | 1997-11-19 | 2000-10-11 | Kowa Co., Ltd. | Novel pyridazine derivatives and drugs containing the same as the active ingredient |
| EP1236720A1 (en) * | 2001-02-28 | 2002-09-04 | Pfizer Products Inc. | Sulfonyl pyridazinone compounds useful as aldose reductase inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| US6872722B2 (en) | 2005-03-29 |
| EP1260224B1 (en) | 2005-02-23 |
| JP2002370984A (ja) | 2002-12-24 |
| DE60203026D1 (de) | 2005-03-31 |
| CN1390547A (zh) | 2003-01-15 |
| CZ20021782A3 (cs) | 2003-03-12 |
| EP1260224A1 (en) | 2002-11-27 |
| HUP0201738A2 (hu) | 2003-02-28 |
| ES2236447T3 (es) | 2005-07-16 |
| HUP0201738A3 (en) | 2003-11-28 |
| ATE289510T1 (de) | 2005-03-15 |
| US20030008871A1 (en) | 2003-01-09 |
| ZA200203985B (en) | 2003-11-20 |
| DE60203026T2 (de) | 2006-05-04 |
| PL354128A1 (en) | 2002-12-02 |
| KR20020090321A (ko) | 2002-12-02 |
| SK7332002A3 (en) | 2003-05-02 |
| AU4068502A (en) | 2002-11-28 |
| HU0201738D0 (https=) | 2002-07-29 |
| CA2387007A1 (en) | 2002-11-24 |
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