KR20070034049A - 피롤로피리딘 유도체 - Google Patents
피롤로피리딘 유도체 Download PDFInfo
- Publication number
- KR20070034049A KR20070034049A KR1020077000449A KR20077000449A KR20070034049A KR 20070034049 A KR20070034049 A KR 20070034049A KR 1020077000449 A KR1020077000449 A KR 1020077000449A KR 20077000449 A KR20077000449 A KR 20077000449A KR 20070034049 A KR20070034049 A KR 20070034049A
- Authority
- KR
- South Korea
- Prior art keywords
- methyl
- pyrrolo
- chloro
- pyridine
- compound
- 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.)
- Withdrawn
Links
- 150000005255 pyrrolopyridines Chemical class 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 396
- 208000002193 Pain Diseases 0.000 claims abstract description 33
- 230000000694 effects Effects 0.000 claims abstract description 32
- 230000036407 pain Effects 0.000 claims abstract description 28
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims description 74
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 229930003827 cannabinoid Natural products 0.000 claims description 27
- 239000003557 cannabinoid Substances 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
- 239000003814 drug Substances 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 13
- 208000004296 neuralgia Diseases 0.000 claims description 11
- 125000002757 morpholinyl group Chemical group 0.000 claims description 10
- 208000021722 neuropathic pain Diseases 0.000 claims description 10
- 125000003386 piperidinyl group Chemical group 0.000 claims description 10
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 10
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 230000001404 mediated effect Effects 0.000 claims description 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
- 206010065390 Inflammatory pain Diseases 0.000 claims description 8
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- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
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- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
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- 206010027599 migraine Diseases 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 claims description 4
- 208000004550 Postoperative Pain Diseases 0.000 claims description 4
- 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 4
- 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 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- QLWGYZYYBDYBOE-UHFFFAOYSA-N 3-methyl-7-morpholin-4-yl-n-(oxan-4-yl)-1h-pyrrolo[2,3-c]pyridine-4-carboxamide Chemical compound C=12C(C)=CNC2=C(N2CCOCC2)N=CC=1C(=O)NC1CCOCC1 QLWGYZYYBDYBOE-UHFFFAOYSA-N 0.000 claims description 3
- MPBQXSBNFHDZND-UHFFFAOYSA-N 3-methyl-7-morpholin-4-yl-n-(oxan-4-ylmethyl)-1h-pyrrolo[2,3-c]pyridine-4-carboxamide Chemical compound C=12C(C)=CNC2=C(N2CCOCC2)N=CC=1C(=O)NCC1CCOCC1 MPBQXSBNFHDZND-UHFFFAOYSA-N 0.000 claims description 3
- 206010058019 Cancer Pain Diseases 0.000 claims description 3
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- 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 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- GJBJDECXBAOBFN-UHFFFAOYSA-N [1-methyl-4-[3-(trifluoromethoxy)anilino]pyrrolo[3,2-c]pyridin-7-yl]-morpholin-4-ylmethanone Chemical compound N1=CC(C(=O)N2CCOCC2)=C2N(C)C=CC2=C1NC1=CC=CC(OC(F)(F)F)=C1 GJBJDECXBAOBFN-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- ANQSJAKYEWWXJT-UHFFFAOYSA-N [4-(3,4-dichloroanilino)-1-methylpyrrolo[3,2-c]pyridin-7-yl]-morpholin-4-ylmethanone Chemical compound N1=CC(C(=O)N2CCOCC2)=C2N(C)C=CC2=C1NC1=CC=C(Cl)C(Cl)=C1 ANQSJAKYEWWXJT-UHFFFAOYSA-N 0.000 claims description 2
- YZIZRRMNKPZAEA-UHFFFAOYSA-N [4-(3,5-difluoroanilino)-1-methylpyrrolo[3,2-c]pyridin-7-yl]-morpholin-4-ylmethanone Chemical class N1=CC(C(=O)N2CCOCC2)=C2N(C)C=CC2=C1NC1=CC(F)=CC(F)=C1 YZIZRRMNKPZAEA-UHFFFAOYSA-N 0.000 claims description 2
- BILAIOFJTOGWRN-UHFFFAOYSA-N [4-(3-bromoanilino)-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=CC(Br)=C1 BILAIOFJTOGWRN-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
- KKELVNWOKAKUJN-UHFFFAOYSA-N [4-(3-chloroanilino)-1-methylpyrrolo[3,2-c]pyridin-7-yl]-piperidin-1-ylmethanone Chemical compound N1=CC(C(=O)N2CCCCC2)=C2N(C)C=CC2=C1NC1=CC=CC(Cl)=C1 KKELVNWOKAKUJN-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- MJMNXDBEGNUOHK-UHFFFAOYSA-N [4-(3-fluoroanilino)-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(F)=C1 MJMNXDBEGNUOHK-UHFFFAOYSA-N 0.000 claims description 2
- UNEYTNUMMZWPQV-UHFFFAOYSA-N [4-(4-bromo-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=C(Br)C(Cl)=C1 UNEYTNUMMZWPQV-UHFFFAOYSA-N 0.000 claims description 2
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- 238000011282 treatment Methods 0.000 abstract description 34
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 21
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- 230000007423 decrease Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 492
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 263
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 237
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- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 54
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- C—CHEMISTRY; METALLURGY
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- 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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- 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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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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| CN113271938A (zh) * | 2018-11-30 | 2021-08-17 | 林伯士拉克许米公司 | Tyk2抑制剂和其用途 |
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- 2005-06-07 EP EP05747418A patent/EP1753764B1/en not_active Expired - Lifetime
- 2005-06-07 AU AU2005251913A patent/AU2005251913A1/en not_active Abandoned
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- 2005-06-07 RU RU2006147278/04A patent/RU2006147278A/ru not_active Application Discontinuation
- 2005-06-07 PL PL05747418T patent/PL1753764T3/pl unknown
- 2005-06-07 KR KR1020077000449A patent/KR20070034049A/ko not_active Withdrawn
- 2005-06-07 BR BRPI0511874-3A patent/BRPI0511874A/pt not_active IP Right Cessation
-
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 |
| NO20070067L (no) | 2007-02-09 |
| TW200611695A (en) | 2006-04-16 |
| MXPA06014471A (es) | 2007-03-21 |
| JP2008501758A (ja) | 2008-01-24 |
| UY28945A1 (es) | 2006-01-31 |
| PE20060430A1 (es) | 2006-05-25 |
| US20070219229A1 (en) | 2007-09-20 |
| ATE412651T1 (de) | 2008-11-15 |
| MA28686B1 (fr) | 2007-06-01 |
| ES2317244T3 (es) | 2009-04-16 |
| EP1753764A1 (en) | 2007-02-21 |
| PL1753764T3 (pl) | 2009-04-30 |
| CA2569887A1 (en) | 2005-12-22 |
| DE602005010698D1 (de) | 2008-12-11 |
| HRP20090034T3 (en) | 2009-03-31 |
| IL179603A0 (en) | 2007-05-15 |
| RU2006147278A (ru) | 2008-07-20 |
| EP1753764B1 (en) | 2008-10-29 |
| AR050158A1 (es) | 2006-10-04 |
| HK1104175A1 (en) | 2008-01-04 |
| US7589206B2 (en) | 2009-09-15 |
| DK1753764T3 (da) | 2009-02-16 |
| BRPI0511874A (pt) | 2008-01-15 |
| SI1753764T1 (sl) | 2009-02-28 |
| PT1753764E (pt) | 2009-01-28 |
| AU2005251913A1 (en) | 2005-12-22 |
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| PA0105 | International application |
Patent event date: 20070108 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PC1203 | Withdrawal of no request for examination | ||
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