DE1595909B2 - 3,8-Diazabicyclo eckige Klammer auf 3,2,1 eckige Klammer zu octane und ein Verfahren zu ihrer Herstellung. Ausscheidung aus: 1243689 - Google Patents
3,8-Diazabicyclo eckige Klammer auf 3,2,1 eckige Klammer zu octane und ein Verfahren zu ihrer Herstellung. Ausscheidung aus: 1243689Info
- Publication number
- DE1595909B2 DE1595909B2 DE19631595909 DE1595909A DE1595909B2 DE 1595909 B2 DE1595909 B2 DE 1595909B2 DE 19631595909 DE19631595909 DE 19631595909 DE 1595909 A DE1595909 A DE 1595909A DE 1595909 B2 DE1595909 B2 DE 1595909B2
- Authority
- DE
- Germany
- Prior art keywords
- octane
- diazabicyclo
- propionyl
- square bracket
- preparation
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 6
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 title description 8
- -1 p-chlorocinnamyl Chemical group 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 7
- WBIVDDQUIOYQLE-UHFFFAOYSA-N 1-(4,6-diazabicyclo[3.2.1]octan-6-yl)propan-1-one Chemical compound C1C2N(C(=O)CC)CC1CCN2 WBIVDDQUIOYQLE-UHFFFAOYSA-N 0.000 claims description 3
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 208000002193 Pain Diseases 0.000 description 4
- 230000036407 pain Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- LKDJYZBKCVSODK-UHFFFAOYSA-N 3,8-diazabicyclo[3.2.1]octane Chemical compound C1NCC2CCC1N2 LKDJYZBKCVSODK-UHFFFAOYSA-N 0.000 description 2
- 208000000114 Pain Threshold Diseases 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000037040 pain threshold Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- MAQBLRFYCNOQJD-UHFFFAOYSA-N 1-(3-benzyl-3,8-diazabicyclo[3.2.1]octan-8-yl)propan-1-one Chemical compound CCC(=O)N1C(C2)CCC1CN2CC1=CC=CC=C1 MAQBLRFYCNOQJD-UHFFFAOYSA-N 0.000 description 1
- QXMPIEOTDBYZDL-UHFFFAOYSA-N 3-benzyl-3,8-diazabicyclo[3.2.1]octane Chemical compound C1C(N2)CCC2CN1CC1=CC=CC=C1 QXMPIEOTDBYZDL-UHFFFAOYSA-N 0.000 description 1
- YCNGCDHLCHTUCQ-UHFFFAOYSA-N CCC(C(CCCN)(C1=CC=CC=C1)C1=CC=CC=C1)=O Chemical compound CCC(C(CCCN)(C1=CC=CC=C1)C1=CC=CC=C1)=O YCNGCDHLCHTUCQ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- IWTYTFSSTWXZFU-QPJJXVBHSA-N [(e)-3-chloroprop-1-enyl]benzene Chemical compound ClC\C=C\C1=CC=CC=C1 IWTYTFSSTWXZFU-QPJJXVBHSA-N 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2315762A GB988526A (en) | 1962-06-15 | 1962-06-15 | Diazabicyclooctanes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1595909A1 DE1595909A1 (de) | 1970-02-26 |
| DE1595909B2 true DE1595909B2 (de) | 1974-07-04 |
Family
ID=10191086
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631595909 Pending DE1595909B2 (de) | 1962-06-15 | 1963-06-14 | 3,8-Diazabicyclo eckige Klammer auf 3,2,1 eckige Klammer zu octane und ein Verfahren zu ihrer Herstellung. Ausscheidung aus: 1243689 |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT245575B (en:Method) |
| BE (1) | BE633541A (en:Method) |
| CH (1) | CH435306A (en:Method) |
| DE (1) | DE1595909B2 (en:Method) |
| DK (1) | DK122524B (en:Method) |
| ES (1) | ES288611A1 (en:Method) |
| FI (1) | FI46256C (en:Method) |
| GB (1) | GB988526A (en:Method) |
| SE (1) | SE329169B (en:Method) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008521776A (ja) * | 2004-11-30 | 2008-06-26 | ノイロサーチ アクティーゼルスカブ | コリン作動性リガンドとしての新規なジアザ二環式アリール誘導体 |
-
1962
- 1962-06-15 GB GB2315762A patent/GB988526A/en not_active Expired
-
1963
- 1963-05-29 DK DK253963A patent/DK122524B/da unknown
- 1963-05-31 ES ES288611A patent/ES288611A1/es not_active Expired
- 1963-06-12 BE BE633541A patent/BE633541A/fr unknown
- 1963-06-13 SE SE655663A patent/SE329169B/xx unknown
- 1963-06-14 DE DE19631595909 patent/DE1595909B2/de active Pending
- 1963-06-14 CH CH742063A patent/CH435306A/fr unknown
- 1963-06-14 AT AT481063A patent/AT245575B/de active
- 1963-06-15 FI FI122163A patent/FI46256C/fi active
Also Published As
| Publication number | Publication date |
|---|---|
| ES288611A1 (es) | 1963-11-01 |
| DE1595909A1 (de) | 1970-02-26 |
| FI46256B (en:Method) | 1972-10-31 |
| AT245575B (de) | 1966-03-10 |
| FI46256C (fi) | 1973-02-12 |
| BE633541A (fr) | 1963-10-21 |
| CH435306A (fr) | 1967-05-15 |
| GB988526A (en) | 1965-04-07 |
| SE329169B (en:Method) | 1970-10-05 |
| DK122524B (da) | 1972-03-13 |
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