CA2465632A1 - Treatment of insulin resistance syndrome and type 2 diabetes with pde9 inhibitors - Google Patents
Treatment of insulin resistance syndrome and type 2 diabetes with pde9 inhibitors Download PDFInfo
- Publication number
- CA2465632A1 CA2465632A1 CA002465632A CA2465632A CA2465632A1 CA 2465632 A1 CA2465632 A1 CA 2465632A1 CA 002465632 A CA002465632 A CA 002465632A CA 2465632 A CA2465632 A CA 2465632A CA 2465632 A1 CA2465632 A1 CA 2465632A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- prodrug
- inhibitor
- optionally substituted
- solvate
- 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.)
- Abandoned
Links
- 229940076380 PDE9 inhibitor Drugs 0.000 title claims abstract description 85
- 208000031773 Insulin resistance syndrome Diseases 0.000 title claims abstract description 43
- 208000001072 type 2 diabetes mellitus Diseases 0.000 title claims abstract description 32
- 238000011282 treatment Methods 0.000 title description 21
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 claims abstract description 82
- RVEJWGYZBXCGGM-DNVCBOLYSA-N chembl2179094 Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)C)N1CC1=CC=CC=C1 RVEJWGYZBXCGGM-DNVCBOLYSA-N 0.000 claims abstract description 72
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 43
- 241000124008 Mammalia Species 0.000 claims abstract description 41
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- 150000001875 compounds Chemical class 0.000 claims description 124
- 239000000651 prodrug Substances 0.000 claims description 106
- 229940002612 prodrug Drugs 0.000 claims description 106
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 94
- -1 phenoxy, phenyl Chemical group 0.000 claims description 93
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- 125000005843 halogen group Chemical group 0.000 claims description 48
- 229910052757 nitrogen Inorganic materials 0.000 claims description 48
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- 229910052717 sulfur Inorganic materials 0.000 claims description 10
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- UORHIBXCPUHXFY-UHFFFAOYSA-N 5-[(3-chlorophenyl)methyl]-3-propan-2-yl-2,4-dihydropyrazolo[4,3-d]pyrimidin-7-one Chemical group CC(C)C1=NNC(C(N2)=O)=C1N=C2CC1=CC=CC(Cl)=C1 UORHIBXCPUHXFY-UHFFFAOYSA-N 0.000 claims description 9
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- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 5
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 claims description 5
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 claims description 5
- 102000004169 proteins and genes Human genes 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 58
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 11
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
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- 238000000034 method Methods 0.000 abstract description 32
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 80
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
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| US33698101P | 2001-11-02 | 2001-11-02 | |
| US60/336,981 | 2001-11-02 | ||
| PCT/IB2002/003754 WO2003037432A1 (en) | 2001-11-02 | 2002-09-12 | Treatment of insulin resistance syndrome and type 2 diabetes with pde9 inhibitors |
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| CA2465632A1 true CA2465632A1 (en) | 2003-05-08 |
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| EP (1) | EP1444009A1 (https=) |
| JP (1) | JP2005508978A (https=) |
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| HU (1) | HUP0401998A2 (https=) |
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| PL (1) | PL370599A1 (https=) |
| WO (1) | WO2003037432A1 (https=) |
| ZA (1) | ZA200402173B (https=) |
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| US9364521B2 (en) | 2012-06-04 | 2016-06-14 | Diamedica Inc. | Human tissue kallikrein 1 glycosylation isoforms |
| US9616015B2 (en) | 2012-05-25 | 2017-04-11 | Diamedica Inc. | Formulations of human tissue kallikrein-1 for parenteral delivery and related methods |
| US11857608B2 (en) | 2017-03-09 | 2024-01-02 | Diamedica Inc. | Dosage forms of tissue kallikrein 1 |
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| US4666908A (en) * | 1985-04-05 | 1987-05-19 | Warner-Lambert Company | 5-Substituted pyrazolo[4,3-d]pyrimidine-7-ones and methods of use |
| DE19541264A1 (de) * | 1995-11-06 | 1997-05-07 | Bayer Ag | Purin-6-on-derivate |
| AU722514B2 (en) * | 1995-12-28 | 2000-08-03 | Fujisawa Pharmaceutical Co., Ltd. | Benzimidazole derivatives |
| GB9722520D0 (en) * | 1997-10-24 | 1997-12-24 | Pfizer Ltd | Compounds |
| US6444816B1 (en) * | 1997-10-27 | 2002-09-03 | Dr. Reddy's Research Foundation | Fused 7-oxo-pyrimidinyl compounds, preparation, composition and use thereof |
| US5922595A (en) * | 1997-12-09 | 1999-07-13 | Incyte Pharmaceuticals, Inc. | Cyclic GMP phosphodiesterase |
| US6225456B1 (en) | 1998-05-07 | 2001-05-01 | University Technololy Corporation | Ras suppressor SUR-5 |
| JP2003526608A (ja) | 1998-10-15 | 2003-09-09 | バイオイメージ エイ／エス | 再分布及び／又は標的化での干渉によって得られる特異的治療の介入 |
| WO2002013798A2 (en) * | 2000-08-11 | 2002-02-21 | Pfizer Limited | Treatment of the insulin resistance syndrome with selective cgmp pde5 inhibitors |
| MXPA03006936A (es) * | 2001-02-02 | 2003-11-18 | Pfizer | Tratamiento de diabetes mellitus. |
| AUPR576801A0 (en) | 2001-06-19 | 2001-07-12 | University Of Tasmania | Methods and pharmaceuticals for treating muscle insulin resistance and related conditions |
| EP1444009A1 (en) * | 2001-11-02 | 2004-08-11 | Pfizer Products Inc. | Treatment of insulin resistance syndrome and type 2 diabetes with pde9 inhibitors |
| US20040220186A1 (en) * | 2003-04-30 | 2004-11-04 | Pfizer Inc. | PDE9 inhibitors for treating type 2 diabetes,metabolic syndrome, and cardiovascular disease |
-
2002
- 2002-09-12 EP EP02762720A patent/EP1444009A1/en not_active Withdrawn
- 2002-09-12 PL PL02370599A patent/PL370599A1/xx not_active Application Discontinuation
- 2002-09-12 CN CNA028211529A patent/CN1575191A/zh active Pending
- 2002-09-12 CA CA002465632A patent/CA2465632A1/en not_active Abandoned
- 2002-09-12 MX MXPA04004170A patent/MXPA04004170A/es unknown
- 2002-09-12 JP JP2003539771A patent/JP2005508978A/ja not_active Withdrawn
- 2002-09-12 IL IL16115502A patent/IL161155A0/xx unknown
- 2002-09-12 BR BR0213817-4A patent/BR0213817A/pt not_active IP Right Cessation
- 2002-09-12 WO PCT/IB2002/003754 patent/WO2003037432A1/en not_active Ceased
- 2002-09-12 HU HU0401998A patent/HUP0401998A2/hu unknown
- 2002-09-12 KR KR10-2004-7006251A patent/KR20040053210A/ko not_active Ceased
- 2002-10-29 US US10/283,814 patent/US6967204B2/en not_active Expired - Fee Related
-
2004
- 2004-03-18 ZA ZA200402173A patent/ZA200402173B/en unknown
- 2004-09-15 US US10/942,438 patent/US20050070557A1/en not_active Abandoned
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005112949A1 (en) * | 2004-05-20 | 2005-12-01 | Diamedica Inc. | Use of drug combinations for treating insulin resistance |
| AU2005245240B2 (en) * | 2004-05-20 | 2010-04-29 | Scimar Ltd. | Use of drug combinations for treating insulin resistance |
| US8673964B2 (en) | 2004-05-20 | 2014-03-18 | Diamedica Inc. | Use of drug combinations for treating insulin resistance |
| CN1960735B (zh) * | 2004-05-20 | 2015-07-29 | 代阿麦迪卡股份有限公司 | 药物组合在治疗胰岛素抗性中的应用 |
| US9616015B2 (en) | 2012-05-25 | 2017-04-11 | Diamedica Inc. | Formulations of human tissue kallikrein-1 for parenteral delivery and related methods |
| US9364521B2 (en) | 2012-06-04 | 2016-06-14 | Diamedica Inc. | Human tissue kallikrein 1 glycosylation isoforms |
| US9839678B2 (en) | 2012-06-04 | 2017-12-12 | Diamedica Inc. | Human tissue kallikrein 1 glycosylation isoforms |
| US11857608B2 (en) | 2017-03-09 | 2024-01-02 | Diamedica Inc. | Dosage forms of tissue kallikrein 1 |
| US12329805B2 (en) | 2017-03-09 | 2025-06-17 | Diamedica Inc. | Dosage forms of tissue kallikrein 1 |
Also Published As
| Publication number | Publication date |
|---|---|
| BR0213817A (pt) | 2004-10-19 |
| IL161155A0 (en) | 2004-08-31 |
| US6967204B2 (en) | 2005-11-22 |
| JP2005508978A (ja) | 2005-04-07 |
| CN1575191A (zh) | 2005-02-02 |
| EP1444009A1 (en) | 2004-08-11 |
| US20040023989A1 (en) | 2004-02-05 |
| US20050070557A1 (en) | 2005-03-31 |
| MXPA04004170A (es) | 2004-09-06 |
| KR20040053210A (ko) | 2004-06-23 |
| ZA200402173B (en) | 2005-03-18 |
| WO2003037432A1 (en) | 2003-05-08 |
| PL370599A1 (en) | 2005-05-30 |
| HUP0401998A2 (hu) | 2005-01-28 |
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