CA2023014A1 - Derives de 2-oxo-1-oxa-8-azaspiro/4,5/decane, composes pharmaceutiques les contenant et procede de preparation - Google Patents
Derives de 2-oxo-1-oxa-8-azaspiro/4,5/decane, composes pharmaceutiques les contenant et procede de preparationInfo
- Publication number
- CA2023014A1 CA2023014A1 CA 2023014 CA2023014A CA2023014A1 CA 2023014 A1 CA2023014 A1 CA 2023014A1 CA 2023014 CA2023014 CA 2023014 CA 2023014 A CA2023014 A CA 2023014A CA 2023014 A1 CA2023014 A1 CA 2023014A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- group
- compound
- stands
- oxo
- 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
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 title claims 3
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical class CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 100
- 238000000034 method Methods 0.000 claims abstract description 36
- 239000002253 acid Substances 0.000 claims abstract description 31
- 230000008569 process Effects 0.000 claims abstract description 24
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 21
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 17
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 6
- 208000020016 psychiatric disease Diseases 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 208000026935 allergic disease Diseases 0.000 claims abstract description 3
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 2
- SEUNTAIZLCAWDW-UHFFFAOYSA-N 1-oxa-8-azaspiro[4.5]decan-2-one Chemical class O1C(=O)CCC11CCNCC1 SEUNTAIZLCAWDW-UHFFFAOYSA-N 0.000 claims abstract 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 74
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 17
- 239000004480 active ingredient Substances 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 10
- 239000012948 isocyanate Substances 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- CYCSGNGCLXFNFZ-UHFFFAOYSA-N (4-ethynylpiperidin-4-yl) carbamate Chemical class NC(=O)OC1(C#C)CCNCC1 CYCSGNGCLXFNFZ-UHFFFAOYSA-N 0.000 claims description 8
- 150000002513 isocyanates Chemical class 0.000 claims description 8
- -1 p-toluenesulfonyloxy group Chemical group 0.000 claims description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 7
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- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 6
- 238000007363 ring formation reaction Methods 0.000 claims description 6
- SKGCHBGIBOPGHV-UHFFFAOYSA-N 1,3-dioxolan-2-imine Chemical class N=C1OCCO1 SKGCHBGIBOPGHV-UHFFFAOYSA-N 0.000 claims description 5
- GVZFMFFUAZKMOB-UHFFFAOYSA-N 4-ethynylpiperidin-4-ol Chemical class C#CC1(O)CCNCC1 GVZFMFFUAZKMOB-UHFFFAOYSA-N 0.000 claims description 5
- DTNXRKYDRUCILN-UHFFFAOYSA-N (4-acetylpiperidin-4-yl) carbamate Chemical class NC(=O)OC1(C(=O)C)CCNCC1 DTNXRKYDRUCILN-UHFFFAOYSA-N 0.000 claims description 4
- VWADBHVASFOEHX-UHFFFAOYSA-N 1-(4-hydroxypiperidin-4-yl)ethanone Chemical class CC(=O)C1(O)CCNCC1 VWADBHVASFOEHX-UHFFFAOYSA-N 0.000 claims description 4
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- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 2
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- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 230000001131 transforming effect Effects 0.000 claims description 2
- ASPBBYVNTMIKLA-UHFFFAOYSA-N 2,8-diazaspiro[4.5]decan-3-one Chemical class C1NC(=O)CC21CCNCC2 ASPBBYVNTMIKLA-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 150000002990 phenothiazines Chemical class 0.000 claims 2
- BBGWSPQPOMSKHE-UHFFFAOYSA-N 3-ethyl-4-methylidene-8-[3-[2-(trifluoromethyl)phenothiazin-10-yl]propyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C=C1N(CC)C(=O)OC11CCN(CCCN2C3=CC(=CC=C3SC3=CC=CC=C32)C(F)(F)F)CC1 BBGWSPQPOMSKHE-UHFFFAOYSA-N 0.000 claims 1
- XZFUSMQQQSPRKP-UHFFFAOYSA-N 3-methyl-4-methylidene-8-[3-[2-(trifluoromethyl)phenothiazin-10-yl]propyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C=C1N(C)C(=O)OC11CCN(CCCN2C3=CC(=CC=C3SC3=CC=CC=C32)C(F)(F)F)CC1 XZFUSMQQQSPRKP-UHFFFAOYSA-N 0.000 claims 1
- JZEBQXFICDCIJR-UHFFFAOYSA-N 4-hydroxy-3,4-dimethyl-8-[3-[2-(trifluoromethyl)phenothiazin-10-yl]propyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound CC1(O)N(C)C(=O)OC11CCN(CCCN2C3=CC(=CC=C3SC3=CC=CC=C32)C(F)(F)F)CC1 JZEBQXFICDCIJR-UHFFFAOYSA-N 0.000 claims 1
- IFIWOFWFBVMMGS-UHFFFAOYSA-N 8-[3-(2-chlorophenothiazin-10-yl)propyl]-3-ethyl-4-methylidene-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C=C1N(CC)C(=O)OC11CCN(CCCN2C3=CC(Cl)=CC=C3SC3=CC=CC=C32)CC1 IFIWOFWFBVMMGS-UHFFFAOYSA-N 0.000 claims 1
- KGWRCGIWQWQHMG-UHFFFAOYSA-N 8-[3-(2-chlorophenothiazin-10-yl)propyl]-3-methyl-4-methylidene-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C=C1N(C)C(=O)OC11CCN(CCCN2C3=CC(Cl)=CC=C3SC3=CC=CC=C32)CC1 KGWRCGIWQWQHMG-UHFFFAOYSA-N 0.000 claims 1
- HOCXUVBCALPMRL-UHFFFAOYSA-N 8-[3-(2-chlorophenothiazin-10-yl)propyl]-4-hydroxy-3,4-dimethyl-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound CC1(O)N(C)C(=O)OC11CCN(CCCN2C3=CC(Cl)=CC=C3SC3=CC=CC=C32)CC1 HOCXUVBCALPMRL-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
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Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA 2023014 CA2023014A1 (fr) | 1989-08-10 | 1990-08-09 | Derives de 2-oxo-1-oxa-8-azaspiro/4,5/decane, composes pharmaceutiques les contenant et procede de preparation |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU4093/89 | 1989-08-10 | ||
| CA 2023014 CA2023014A1 (fr) | 1989-08-10 | 1990-08-09 | Derives de 2-oxo-1-oxa-8-azaspiro/4,5/decane, composes pharmaceutiques les contenant et procede de preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2023014A1 true CA2023014A1 (fr) | 1991-02-11 |
Family
ID=4145692
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2023014 Abandoned CA2023014A1 (fr) | 1989-08-10 | 1990-08-09 | Derives de 2-oxo-1-oxa-8-azaspiro/4,5/decane, composes pharmaceutiques les contenant et procede de preparation |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2023014A1 (fr) |
-
1990
- 1990-08-09 CA CA 2023014 patent/CA2023014A1/fr not_active Abandoned
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