CA2318208C - Piperidine and pyrrolidine derivatives comprising a nitric oxide donor for treating stress - Google Patents
Piperidine and pyrrolidine derivatives comprising a nitric oxide donor for treating stress Download PDFInfo
- Publication number
- CA2318208C CA2318208C CA002318208A CA2318208A CA2318208C CA 2318208 C CA2318208 C CA 2318208C CA 002318208 A CA002318208 A CA 002318208A CA 2318208 A CA2318208 A CA 2318208A CA 2318208 C CA2318208 C CA 2318208C
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- tempo
- free radical
- donor
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- 239000002840 nitric oxide donor Substances 0.000 title claims abstract description 22
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title 2
- 150000003235 pyrrolidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims abstract description 50
- -1 superoxide ion Chemical class 0.000 claims abstract description 35
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 238000011282 treatment Methods 0.000 claims abstract description 12
- 206010048554 Endothelial dysfunction Diseases 0.000 claims abstract description 9
- 230000008694 endothelial dysfunction Effects 0.000 claims abstract description 9
- 239000002516 radical scavenger Substances 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 230000036542 oxidative stress Effects 0.000 claims abstract description 7
- 125000003368 amide group Chemical group 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 150000003254 radicals Chemical class 0.000 claims description 24
- 229910002651 NO3 Inorganic materials 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims description 6
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 229910004679 ONO2 Inorganic materials 0.000 claims description 3
- 239000001273 butane Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
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- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical group ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
- 238000006243 chemical reaction Methods 0.000 description 34
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 31
- 229960003711 glyceryl trinitrate Drugs 0.000 description 31
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
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- CMFNMSMUKZHDEY-UHFFFAOYSA-N peroxynitrous acid Chemical compound OON=O CMFNMSMUKZHDEY-UHFFFAOYSA-N 0.000 description 8
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- ZIIQCSMRQKCOCT-YFKPBYRVSA-N S-nitroso-N-acetyl-D-penicillamine Chemical compound CC(=O)N[C@@H](C(O)=O)C(C)(C)SN=O ZIIQCSMRQKCOCT-YFKPBYRVSA-N 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 6
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- 229910006121 SOBr2 Inorganic materials 0.000 description 5
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- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
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Landscapes
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9801398.0A GB9801398D0 (en) | 1998-01-22 | 1998-01-22 | Chemical compounds |
| GB9801398.0 | 1998-01-22 | ||
| PCT/GB1999/000231 WO1999037616A1 (en) | 1998-01-22 | 1999-01-22 | Piperidine and pyrrolidine derivatives comprising a nitric oxide donor for treating stress |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2318208A1 CA2318208A1 (en) | 1999-07-29 |
| CA2318208C true CA2318208C (en) | 2009-09-29 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002318208A Expired - Fee Related CA2318208C (en) | 1998-01-22 | 1999-01-22 | Piperidine and pyrrolidine derivatives comprising a nitric oxide donor for treating stress |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US6448267B1 (https=) |
| EP (1) | EP1124801B1 (https=) |
| JP (1) | JP2002501049A (https=) |
| AT (1) | ATE277012T1 (https=) |
| AU (1) | AU4120699A (https=) |
| CA (1) | CA2318208C (https=) |
| DE (1) | DE69920496T2 (https=) |
| GB (1) | GB9801398D0 (https=) |
| WO (1) | WO1999037616A1 (https=) |
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| US6207713B1 (en) * | 1997-09-17 | 2001-03-27 | Eric T. Fossel | Topical and oral delivery of arginine to cause beneficial effects |
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| GB2349385A (en) * | 1999-04-30 | 2000-11-01 | Teijin Ltd | Organic nitrates and nitrites useful against heart disease |
| IL147112A0 (en) * | 1999-06-14 | 2002-08-14 | Ford Henry Health System | Nitric oxide donors for inducing neurogenesis |
| US7135498B1 (en) | 1999-06-14 | 2006-11-14 | Henry Ford Health System | Nitric oxide donors for inducing neurogenesis |
| KR20010038797A (ko) * | 1999-10-27 | 2001-05-15 | 김길환 | 홍국을 이용한 일산화질소 생성제 조성물 및 이를 이용한 약품 조성물 |
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1998
- 1998-01-22 GB GBGB9801398.0A patent/GB9801398D0/en not_active Ceased
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1999
- 1999-01-22 WO PCT/GB1999/000231 patent/WO1999037616A1/en not_active Ceased
- 1999-01-22 AU AU41206/99A patent/AU4120699A/en not_active Abandoned
- 1999-01-22 JP JP2000528540A patent/JP2002501049A/ja active Pending
- 1999-01-22 AT AT99945671T patent/ATE277012T1/de not_active IP Right Cessation
- 1999-01-22 DE DE69920496T patent/DE69920496T2/de not_active Expired - Lifetime
- 1999-01-22 EP EP99945671A patent/EP1124801B1/en not_active Expired - Lifetime
- 1999-01-22 US US09/600,711 patent/US6448267B1/en not_active Expired - Lifetime
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2002
- 2002-03-06 US US10/093,251 patent/US6455542B1/en not_active Expired - Lifetime
- 2002-07-25 US US10/205,997 patent/US6759430B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US6448267B1 (en) | 2002-09-10 |
| US20030069429A1 (en) | 2003-04-10 |
| AU4120699A (en) | 1999-08-09 |
| WO1999037616A1 (en) | 1999-07-29 |
| ATE277012T1 (de) | 2004-10-15 |
| US6759430B2 (en) | 2004-07-06 |
| GB9801398D0 (en) | 1998-03-18 |
| EP1124801A1 (en) | 2001-08-22 |
| US20020091266A1 (en) | 2002-07-11 |
| DE69920496D1 (de) | 2004-10-28 |
| JP2002501049A (ja) | 2002-01-15 |
| CA2318208A1 (en) | 1999-07-29 |
| DE69920496T2 (de) | 2005-08-25 |
| US6455542B1 (en) | 2002-09-24 |
| EP1124801B1 (en) | 2004-09-22 |
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