CA2569887A1 - Pyrrolopyridine derivatives - Google Patents
Pyrrolopyridine derivatives Download PDFInfo
- Publication number
- CA2569887A1 CA2569887A1 CA002569887A CA2569887A CA2569887A1 CA 2569887 A1 CA2569887 A1 CA 2569887A1 CA 002569887 A CA002569887 A CA 002569887A CA 2569887 A CA2569887 A CA 2569887A CA 2569887 A1 CA2569887 A1 CA 2569887A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- pyrrolo
- chloro
- pyridin
- pyridine
- 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
- 150000005255 pyrrolopyridines Chemical class 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 357
- 238000011282 treatment Methods 0.000 claims abstract description 39
- 230000000694 effects Effects 0.000 claims abstract description 37
- 208000002193 Pain Diseases 0.000 claims abstract description 32
- 230000036407 pain Effects 0.000 claims abstract description 27
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 87
- 238000000034 method Methods 0.000 claims description 69
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 59
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- 229930003827 cannabinoid Natural products 0.000 claims description 26
- 239000003557 cannabinoid Substances 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 241000282414 Homo sapiens Species 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000002757 morpholinyl group Chemical group 0.000 claims description 11
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- SFQQUBOFNDDLMP-UHFFFAOYSA-N [7-(3-chloroanilino)-3-methyl-1h-pyrrolo[2,3-c]pyridin-4-yl]-morpholin-4-ylmethanone Chemical compound N1=CC(C(=O)N2CCOCC2)=C2C(C)=CNC2=C1NC1=CC=CC(Cl)=C1 SFQQUBOFNDDLMP-UHFFFAOYSA-N 0.000 claims description 5
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- GWXAVEFSWFVVBK-UHFFFAOYSA-N [4-(3-chloroanilino)-1-methylpyrrolo[3,2-c]pyridin-7-yl]-pyrrolidin-1-ylmethanone Chemical compound N1=CC(C(=O)N2CCCC2)=C2N(C)C=CC2=C1NC1=CC=CC(Cl)=C1 GWXAVEFSWFVVBK-UHFFFAOYSA-N 0.000 claims description 4
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- YZIZRRMNKPZAEA-UHFFFAOYSA-N [4-(3,5-difluoroanilino)-1-methylpyrrolo[3,2-c]pyridin-7-yl]-morpholin-4-ylmethanone Chemical compound N1=CC(C(=O)N2CCOCC2)=C2N(C)C=CC2=C1NC1=CC(F)=CC(F)=C1 YZIZRRMNKPZAEA-UHFFFAOYSA-N 0.000 claims description 2
- BUUDGGJSXRDBIW-UHFFFAOYSA-N [4-(3-chloro-4-fluoroanilino)-1-methylpyrrolo[3,2-c]pyridin-7-yl]-piperidin-1-ylmethanone Chemical compound N1=CC(C(=O)N2CCCCC2)=C2N(C)C=CC2=C1NC1=CC=C(F)C(Cl)=C1 BUUDGGJSXRDBIW-UHFFFAOYSA-N 0.000 claims description 2
- GYJNYXLNSJFKCD-UHFFFAOYSA-N [4-(3-chloroanilino)-1-ethylpyrrolo[3,2-c]pyridin-7-yl]-morpholin-4-ylmethanone Chemical compound N1=CC(C(=O)N2CCOCC2)=C2N(CC)C=CC2=C1NC1=CC=CC(Cl)=C1 GYJNYXLNSJFKCD-UHFFFAOYSA-N 0.000 claims description 2
- VARGWBUXBMFVJN-UHFFFAOYSA-N [4-(3-chloroanilino)-1-methylpyrrolo[3,2-c]pyridin-7-yl]-morpholin-4-ylmethanone Chemical compound N1=CC(C(=O)N2CCOCC2)=C2N(C)C=CC2=C1NC1=CC=CC(Cl)=C1 VARGWBUXBMFVJN-UHFFFAOYSA-N 0.000 claims description 2
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- 230000000063 preceeding effect Effects 0.000 claims 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- YONUUTWZHGJWCN-UHFFFAOYSA-N 1-[3-(trifluoromethoxy)phenyl]pyrrolo[3,2-c]pyridin-4-amine Chemical compound FC(OC=1C=C(C=CC=1)N1C=CC=2C(=NC=CC=21)N)(F)F YONUUTWZHGJWCN-UHFFFAOYSA-N 0.000 claims 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
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- WKCPCYFYEPICOD-UHFFFAOYSA-N [1-methyl-4-[3-(trifluoromethoxy)anilino]pyrrolo[3,2-c]pyridin-7-yl]-piperidin-1-ylmethanone Chemical compound N1=CC(C(=O)N2CCCCC2)=C2N(C)C=CC2=C1NC1=CC=CC(OC(F)(F)F)=C1 WKCPCYFYEPICOD-UHFFFAOYSA-N 0.000 claims 1
- ITGOWTLRFUQTMF-UHFFFAOYSA-N [4-(3,4-dichloroanilino)-1-methylpyrrolo[3,2-c]pyridin-7-yl]-morpholin-4-ylmethanone;hydrochloride Chemical compound Cl.N1=CC(C(=O)N2CCOCC2)=C2N(C)C=CC2=C1NC1=CC=C(Cl)C(Cl)=C1 ITGOWTLRFUQTMF-UHFFFAOYSA-N 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
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Classifications
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- 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
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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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
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- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
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- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Medicinal Chemistry (AREA)
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- Neurosurgery (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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| GB0424950.4 | 2004-11-11 | ||
| GB0424950A GB0424950D0 (en) | 2004-11-11 | 2004-11-11 | Compounds |
| PCT/EP2005/006182 WO2005121140A1 (en) | 2004-06-09 | 2005-06-07 | Pyrrolopyridine derivatives |
Publications (1)
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| CA2569887A1 true CA2569887A1 (en) | 2005-12-22 |
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| CA002569887A Abandoned CA2569887A1 (en) | 2004-06-09 | 2005-06-07 | Pyrrolopyridine derivatives |
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| BRPI0614272A2 (pt) * | 2005-08-09 | 2011-03-22 | Glaxo Group Ltd | derivados de imidazopiridinas como ligantes de receptores canabinóides |
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| WO2004074286A1 (en) | 2003-02-14 | 2004-09-02 | Wyeth | Heterocyclyl-3-sulfonylazaindole or -azaindazole derivatives as 5-hydroxytryptamine-6 ligands |
| US20040214856A1 (en) | 2003-04-23 | 2004-10-28 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
| DK1753764T3 (da) | 2004-06-09 | 2009-02-16 | Glaxo Group Ltd | Pyrrolopyridin-derivater |
-
2005
- 2005-06-07 DK DK05747418T patent/DK1753764T3/da active
- 2005-06-07 BR BRPI0511874-3A patent/BRPI0511874A/pt not_active IP Right Cessation
- 2005-06-07 ES ES05747418T patent/ES2317244T3/es not_active Expired - Lifetime
- 2005-06-07 WO PCT/EP2005/006182 patent/WO2005121140A1/en not_active Ceased
- 2005-06-07 HR HR20090034T patent/HRP20090034T3/xx unknown
- 2005-06-07 DE DE602005010698T patent/DE602005010698D1/de not_active Expired - Lifetime
- 2005-06-07 AT AT05747418T patent/ATE412651T1/de not_active IP Right Cessation
- 2005-06-07 UY UY28945A patent/UY28945A1/es unknown
- 2005-06-07 PT PT05747418T patent/PT1753764E/pt unknown
- 2005-06-07 JP JP2007526300A patent/JP2008501758A/ja not_active Withdrawn
- 2005-06-07 TW TW094118669A patent/TW200611695A/zh unknown
- 2005-06-07 PL PL05747418T patent/PL1753764T3/pl unknown
- 2005-06-07 AR ARP050102327A patent/AR050158A1/es unknown
- 2005-06-07 MX MXPA06014471A patent/MXPA06014471A/es unknown
- 2005-06-07 PE PE2005000651A patent/PE20060430A1/es not_active Application Discontinuation
- 2005-06-07 AU AU2005251913A patent/AU2005251913A1/en not_active Abandoned
- 2005-06-07 EP EP05747418A patent/EP1753764B1/en not_active Expired - Lifetime
- 2005-06-07 CA CA002569887A patent/CA2569887A1/en not_active Abandoned
- 2005-06-07 KR KR1020077000449A patent/KR20070034049A/ko not_active Withdrawn
- 2005-06-07 SI SI200530497T patent/SI1753764T1/sl unknown
- 2005-06-07 RU RU2006147278/04A patent/RU2006147278A/ru not_active Application Discontinuation
- 2005-06-07 US US11/570,099 patent/US7589206B2/en not_active Expired - Fee Related
-
2006
- 2006-11-27 IL IL179603A patent/IL179603A0/en unknown
- 2006-12-28 MA MA29569A patent/MA28686B1/fr unknown
-
2007
- 2007-01-04 NO NO20070067A patent/NO20070067L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005121140A1 (en) | 2005-12-22 |
| HRP20090034T3 (en) | 2009-03-31 |
| US20070219229A1 (en) | 2007-09-20 |
| UY28945A1 (es) | 2006-01-31 |
| PT1753764E (pt) | 2009-01-28 |
| RU2006147278A (ru) | 2008-07-20 |
| SI1753764T1 (sl) | 2009-02-28 |
| AU2005251913A1 (en) | 2005-12-22 |
| IL179603A0 (en) | 2007-05-15 |
| HK1104175A1 (en) | 2008-01-04 |
| PE20060430A1 (es) | 2006-05-25 |
| US7589206B2 (en) | 2009-09-15 |
| KR20070034049A (ko) | 2007-03-27 |
| MA28686B1 (fr) | 2007-06-01 |
| PL1753764T3 (pl) | 2009-04-30 |
| TW200611695A (en) | 2006-04-16 |
| BRPI0511874A (pt) | 2008-01-15 |
| AR050158A1 (es) | 2006-10-04 |
| EP1753764B1 (en) | 2008-10-29 |
| EP1753764A1 (en) | 2007-02-21 |
| ATE412651T1 (de) | 2008-11-15 |
| JP2008501758A (ja) | 2008-01-24 |
| DK1753764T3 (da) | 2009-02-16 |
| NO20070067L (no) | 2007-02-09 |
| ES2317244T3 (es) | 2009-04-16 |
| MXPA06014471A (es) | 2007-03-21 |
| DE602005010698D1 (de) | 2008-12-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |