GB1115817A - 2-aza-bicyclo[2,2,2]octanones and compositions containing them - Google Patents
2-aza-bicyclo[2,2,2]octanones and compositions containing themInfo
- Publication number
- GB1115817A GB1115817A GB3610665A GB3610665A GB1115817A GB 1115817 A GB1115817 A GB 1115817A GB 3610665 A GB3610665 A GB 3610665A GB 3610665 A GB3610665 A GB 3610665A GB 1115817 A GB1115817 A GB 1115817A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- formula
- hydrogen
- compound
- acid
- 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.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 9
- 239000001257 hydrogen Substances 0.000 abstract 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 9
- 150000001875 compounds Chemical class 0.000 abstract 7
- 239000002253 acid Substances 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- QAHZIGHCEBUNGT-QMGFNSACSA-N (5r,6s,7s,8r,9r)-6,7,8-trihydroxy-9-(hydroxymethyl)-1,3-diazaspiro[4.5]decane-2,4-dione Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)C[C@]11C(=O)NC(=O)N1 QAHZIGHCEBUNGT-QMGFNSACSA-N 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 2
- WOXWUZCRWJWTRT-UHFFFAOYSA-N 1-amino-1-cyclohexanecarboxylic acid Chemical class OC(=O)C1(N)CCCCC1 WOXWUZCRWJWTRT-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 230000029936 alkylation Effects 0.000 abstract 2
- 238000005804 alkylation reaction Methods 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- DMQDISNGEDGSQB-UHFFFAOYSA-N 1-aminocyclohexane-1,4-dicarboxylic acid hydrochloride Chemical compound Cl.NC1(CCC(CC1)C(=O)O)C(=O)O DMQDISNGEDGSQB-UHFFFAOYSA-N 0.000 abstract 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 1
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 abstract 1
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 abstract 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 abstract 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 abstract 1
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 abstract 1
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- -1 alkali metal cyanide Chemical class 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 229960000212 aminophenazone Drugs 0.000 abstract 1
- 239000001099 ammonium carbonate Substances 0.000 abstract 1
- 235000012501 ammonium carbonate Nutrition 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000002921 anti-spasmodic effect Effects 0.000 abstract 1
- 229940124575 antispasmodic agent Drugs 0.000 abstract 1
- 229940125717 barbiturate Drugs 0.000 abstract 1
- 229960001948 caffeine Drugs 0.000 abstract 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229960004126 codeine Drugs 0.000 abstract 1
- 230000020335 dealkylation Effects 0.000 abstract 1
- 238000006900 dealkylation reaction Methods 0.000 abstract 1
- 239000002934 diuretic Substances 0.000 abstract 1
- 229940030606 diuretics Drugs 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 238000010930 lactamization Methods 0.000 abstract 1
- 150000003951 lactams Chemical class 0.000 abstract 1
- 229960004815 meprobamate Drugs 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229960003893 phenacetin Drugs 0.000 abstract 1
- 239000006187 pill Substances 0.000 abstract 1
- 238000005932 reductive alkylation reaction Methods 0.000 abstract 1
- 229960000581 salicylamide Drugs 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 239000000829 suppository Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 239000003204 tranquilizing agent Substances 0.000 abstract 1
- 230000002936 tranquilizing effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/06—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing isoquinuclidine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3610665A GB1115817A (en) | 1965-08-23 | 1965-08-23 | 2-aza-bicyclo[2,2,2]octanones and compositions containing them |
| BE685852D BE685852A (enrdf_load_stackoverflow) | 1965-08-23 | 1966-08-23 | |
| FR73941A FR1522236A (fr) | 1965-08-23 | 1966-08-23 | Procédé pour préparer les acides, esters, et amides 2-azabicyclo[2, 2, 2]octanone-(3)-1-carboxyliques et leurs dérivés |
| NL6611855A NL6611855A (enrdf_load_stackoverflow) | 1965-08-23 | 1966-08-23 | |
| FR84177A FR5982M (enrdf_load_stackoverflow) | 1965-08-23 | 1966-11-18 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3610665A GB1115817A (en) | 1965-08-23 | 1965-08-23 | 2-aza-bicyclo[2,2,2]octanones and compositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1115817A true GB1115817A (en) | 1968-05-29 |
Family
ID=10385028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3610665A Expired GB1115817A (en) | 1965-08-23 | 1965-08-23 | 2-aza-bicyclo[2,2,2]octanones and compositions containing them |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE685852A (enrdf_load_stackoverflow) |
| FR (1) | FR5982M (enrdf_load_stackoverflow) |
| GB (1) | GB1115817A (enrdf_load_stackoverflow) |
| NL (1) | NL6611855A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003007949A1 (en) * | 2001-07-18 | 2003-01-30 | Merck & Co., Inc. | Bridged piperidine derivatives as melanocortin receptor agonists |
-
1965
- 1965-08-23 GB GB3610665A patent/GB1115817A/en not_active Expired
-
1966
- 1966-08-23 NL NL6611855A patent/NL6611855A/xx unknown
- 1966-08-23 BE BE685852D patent/BE685852A/xx unknown
- 1966-11-18 FR FR84177A patent/FR5982M/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003007949A1 (en) * | 2001-07-18 | 2003-01-30 | Merck & Co., Inc. | Bridged piperidine derivatives as melanocortin receptor agonists |
| US7115628B2 (en) | 2001-07-18 | 2006-10-03 | Merck & Co., Inc. | Bridged piperidine derivatives as melanocortin receptor agonists |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6611855A (enrdf_load_stackoverflow) | 1967-02-24 |
| FR5982M (enrdf_load_stackoverflow) | 1968-04-22 |
| BE685852A (enrdf_load_stackoverflow) | 1967-02-01 |
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