CA2151507A1 - Pharmaceutical composition containing bicyclic type compounds - Google Patents
Pharmaceutical composition containing bicyclic type compoundsInfo
- Publication number
- CA2151507A1 CA2151507A1 CA002151507A CA2151507A CA2151507A1 CA 2151507 A1 CA2151507 A1 CA 2151507A1 CA 002151507 A CA002151507 A CA 002151507A CA 2151507 A CA2151507 A CA 2151507A CA 2151507 A1 CA2151507 A1 CA 2151507A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- cyano
- hydrogen
- optionally substituted
- substituted
- 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.)
- Granted
Links
- 125000002619 bicyclic group Chemical group 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical class 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- -1 perfluoro Chemical group 0.000 abstract 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 abstract 1
- 125000006552 (C3-C8) cycloalkyl group Chemical class 0.000 abstract 1
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Chemical group 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 125000004685 alkoxythiocarbonyl group Chemical group 0.000 abstract 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 abstract 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 abstract 1
- 125000005129 aryl carbonyl group Chemical group 0.000 abstract 1
- 125000005199 aryl carbonyloxy group Chemical group 0.000 abstract 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 1
- 125000005469 ethylenyl group Chemical group 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 abstract 1
- 125000005204 heteroarylcarbonyloxy group Chemical group 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical class C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 abstract 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 150000003852 triazoles Chemical class 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/68—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with nitrogen atoms directly attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
A compound of formula (I) or pharmaceutically acceptable salt thereof wherein:
either Y is N and R2 is hydrogen, or Y is C-R1 where: either one of R1 and R2 is hydrogen and the other is selected from the class of hydrogen, C3-8 cycloalkyl, C1-6 alkyl optionally interrupted by oxygen or substituted by hydroxy, C1-6 alkoxy or substituted aminocarbonyl, C1-6 alkylcarbonyl, C1-6 alkoxycarbonyl, C1-6 alkylcarbonyloxy, C1-6 alkoxy, nitro, cyano, halo, trifluoromethyl, CF3S, or a group CF3-A-, where A is -CF2-, -CO-, -CH2-, CH(OH), SO2, SO, CH2-O, or CONH, or a group CF2H-A'- where A' is oxygen, sulphur, SO, SO2, CF2 or CFH; trifluoromethoxy, C1-6 alkylsulphinyl, perfluoro C2-6 alkylsulphonyl, C1-6 alkylsulphonyl, C1-6 alkoxysulphinyl, C1-6 alkoxysulphonyl, aryl, heteroaryl, arylcarbonyl, heteroarylcarbonyl, phosphono, arylcarbonyloxy, heteroarylcarbonyloxy, arylsulphinyl, heteroarylsulphinyl, arylsulphonyl, heteroarylsulphonyl in which any aromatic moiety is optionally substituted, C1-6 alkylcarbonylamino, C1-6 alkoxycarbonylamino, C1-6 alkyl-thiocarbonyl, C1-6 alkoxythiocarbonyl, C1-6 alkyl-thiocarbonyloxy, 1-mercapto C2-7 alkyl, formyl, or aminosulphinyl, aminosulphonyl or aminocarbonyl, any amino moiety being optionally substituted by one or two C1-6 alkyl groups, or C1-6 alkylsulphinylamino, C1-6 alky1sulphonylamino, C1-6 alkoxysulphinylamino or C1-6 alkoxysulphonylamino, or ethylenyl terminally substituted by C1-6 alkylcarbonyl, nitro or cyano, or -C(C1-6 alkyl)NOH or -C(C1-6 alkyl)NNH2, or one of R1 and R2 is nitro, cyano or C1-3 alkylcarbonyl and the other is methoxy or amino optionally substituted by one or two C1-6 alkyl or by C2-7 alkanoyl; or R1 and R2 together sit -(CH2)4- or -CH=CH-CH=CH-, or form an optionally substituted triazole or oxadiazole ring; and X is oxygen or NR10 where R10 is hydrogen or C1-6 alkyl with the proviso that the compound is not racemic cis-4-benzoylamino-6-cyano-3,4-dihydro-2,2-dimethyl-2H-benzo[b]pyran-3-ol.
either Y is N and R2 is hydrogen, or Y is C-R1 where: either one of R1 and R2 is hydrogen and the other is selected from the class of hydrogen, C3-8 cycloalkyl, C1-6 alkyl optionally interrupted by oxygen or substituted by hydroxy, C1-6 alkoxy or substituted aminocarbonyl, C1-6 alkylcarbonyl, C1-6 alkoxycarbonyl, C1-6 alkylcarbonyloxy, C1-6 alkoxy, nitro, cyano, halo, trifluoromethyl, CF3S, or a group CF3-A-, where A is -CF2-, -CO-, -CH2-, CH(OH), SO2, SO, CH2-O, or CONH, or a group CF2H-A'- where A' is oxygen, sulphur, SO, SO2, CF2 or CFH; trifluoromethoxy, C1-6 alkylsulphinyl, perfluoro C2-6 alkylsulphonyl, C1-6 alkylsulphonyl, C1-6 alkoxysulphinyl, C1-6 alkoxysulphonyl, aryl, heteroaryl, arylcarbonyl, heteroarylcarbonyl, phosphono, arylcarbonyloxy, heteroarylcarbonyloxy, arylsulphinyl, heteroarylsulphinyl, arylsulphonyl, heteroarylsulphonyl in which any aromatic moiety is optionally substituted, C1-6 alkylcarbonylamino, C1-6 alkoxycarbonylamino, C1-6 alkyl-thiocarbonyl, C1-6 alkoxythiocarbonyl, C1-6 alkyl-thiocarbonyloxy, 1-mercapto C2-7 alkyl, formyl, or aminosulphinyl, aminosulphonyl or aminocarbonyl, any amino moiety being optionally substituted by one or two C1-6 alkyl groups, or C1-6 alkylsulphinylamino, C1-6 alky1sulphonylamino, C1-6 alkoxysulphinylamino or C1-6 alkoxysulphonylamino, or ethylenyl terminally substituted by C1-6 alkylcarbonyl, nitro or cyano, or -C(C1-6 alkyl)NOH or -C(C1-6 alkyl)NNH2, or one of R1 and R2 is nitro, cyano or C1-3 alkylcarbonyl and the other is methoxy or amino optionally substituted by one or two C1-6 alkyl or by C2-7 alkanoyl; or R1 and R2 together sit -(CH2)4- or -CH=CH-CH=CH-, or form an optionally substituted triazole or oxadiazole ring; and X is oxygen or NR10 where R10 is hydrogen or C1-6 alkyl with the proviso that the compound is not racemic cis-4-benzoylamino-6-cyano-3,4-dihydro-2,2-dimethyl-2H-benzo[b]pyran-3-ol.
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929225858A GB9225858D0 (en) | 1992-12-11 | 1992-12-11 | Novel treatment |
| GB929225861A GB9225861D0 (en) | 1992-12-11 | 1992-12-11 | Novel treatment |
| GB9225858.1 | 1992-12-11 | ||
| GB9225861.5 | 1992-12-11 | ||
| GB929225857A GB9225857D0 (en) | 1992-12-11 | 1992-12-11 | Novel treatment |
| GB9225857.3 | 1992-12-11 | ||
| PCT/GB1993/002513 WO1994013657A1 (en) | 1992-12-11 | 1993-12-08 | Pharmaceutical composition containing bicyclic type compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2151507A1 true CA2151507A1 (en) | 1994-06-23 |
| CA2151507C CA2151507C (en) | 2006-10-03 |
Family
ID=37101722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002151507A Expired - Lifetime CA2151507C (en) | 1992-12-11 | 1993-12-08 | Pharmaceutical composition containing bicyclic type compounds |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2151507C (en) |
-
1993
- 1993-12-08 CA CA002151507A patent/CA2151507C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2151507C (en) | 2006-10-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20131209 |