IE40945B1 - Benzomorphanes derivatives - Google Patents
Benzomorphanes derivativesInfo
- Publication number
- IE40945B1 IE40945B1 IE505/75A IE50575A IE40945B1 IE 40945 B1 IE40945 B1 IE 40945B1 IE 505/75 A IE505/75 A IE 505/75A IE 50575 A IE50575 A IE 50575A IE 40945 B1 IE40945 B1 IE 40945B1
- Authority
- IE
- Ireland
- Prior art keywords
- methyl
- formula
- action
- denotes hydrogen
- morphine
- Prior art date
Links
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 229960005181 morphine Drugs 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 238000007126 N-alkylation reaction Methods 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
- C07D221/26—Benzomorphans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Novel 2-tetrahydrofurfuryl-6-7-benzomorphans of the accompanying formula I, in which R<1> denotes methyl, ethyl or propyl; R<2> denotes hydrogen, methyl or ethyl; R<3> denotes hydrogen or methyl; and R<4> denotes hydrogen, alkyl having 1 to 4 carbon atoms or acyl having 2 to 5 carbon atoms, are prepared by introducing the tetrahydrofurfuryl radical into appropriately substituted norbenzomorphans by the methods of N-alkylation. The resulting bases of the formula I can then be converted into their acid addition salts. The compounds of the formula I and their acid addition salts are distinguished by a therapeutically utilisable action on the central nervous system. Particularly to be emphasised is their analgesic action, which frequently exceeds that of morphine, without exhibiting the undesired side effects of morphine, e.g. the addictive action. <IMAGE>
[GB1496418A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2411382A DE2411382C3 (en) | 1974-03-09 | 1974-03-09 | 2-Tetrahydrofurfuryl-6,7-benzomorphane, process for the preparation and their use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE40945L IE40945L (en) | 1975-09-09 |
| IE40945B1 true IE40945B1 (en) | 1979-09-12 |
Family
ID=5909593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE505/75A IE40945B1 (en) | 1974-03-09 | 1975-03-07 | Benzomorphanes derivatives |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS5827275B2 (en) |
| AT (1) | AT344332B (en) |
| BE (1) | BE826440A (en) |
| BG (3) | BG25087A3 (en) |
| CA (1) | CA1049511A (en) |
| CH (8) | CH612425A5 (en) |
| CS (1) | CS188221B2 (en) |
| DD (1) | DD119236A5 (en) |
| DE (1) | DE2411382C3 (en) |
| DK (1) | DK137188C (en) |
| ES (6) | ES440348A1 (en) |
| FI (1) | FI63571C (en) |
| FR (1) | FR2262984B1 (en) |
| GB (1) | GB1496418A (en) |
| HU (1) | HU177408B (en) |
| IE (1) | IE40945B1 (en) |
| IL (1) | IL46760A (en) |
| NL (1) | NL7502724A (en) |
| NO (1) | NO141800C (en) |
| PH (1) | PH14127A (en) |
| PL (3) | PL93499B1 (en) |
| RO (2) | RO70051A (en) |
| SE (1) | SE421919B (en) |
| SU (3) | SU577982A3 (en) |
| ZA (1) | ZA751394B (en) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2716687A1 (en) * | 1977-04-15 | 1978-10-19 | Boehringer Sohn Ingelheim | 2'-HYDROXY-2- (5-ISOXAZOLYLMETHYL) -6.7BENZOMORPHANES, THEIR ACID ADDITIONAL SALTS AND MEDICINAL PRODUCTS CONTAINING THEM |
| DE2828039A1 (en) * | 1978-06-26 | 1980-01-10 | Boehringer Sohn Ingelheim | 2- (2-ALKOXYETHYL) -2'-HYDROXY-6,7-BENZOMORPHANES THEIR ACID ADDITION SALTS, THESE MEDICINAL PRODUCTS, AND METHOD FOR THE PRODUCTION THEREOF |
| US6492420B2 (en) | 1995-03-10 | 2002-12-10 | Photocure As | Esters of 5-aminolevulinic acid as photosensitizing agents in photochemotherapy |
| US7530461B2 (en) | 1995-03-10 | 2009-05-12 | Photocure Asa | Esters of 5-aminolevulinic acid as photosensitizing agents in photochemotherapy |
| US6034267A (en) * | 1995-03-10 | 2000-03-07 | Photocure As | Esters of 5-aminolevulinic acid as photosensitizing agents in photochemotherapy |
| US6992107B1 (en) | 1995-03-10 | 2006-01-31 | Photocure Asa | Esters of 5-aminolevulinic acid and their use as photosensitizing compounds in photochemotherapy |
| GB0018528D0 (en) | 2000-07-27 | 2000-09-13 | Photocure Asa | Compounds |
| US6723750B2 (en) | 2002-03-15 | 2004-04-20 | Allergan, Inc. | Photodynamic therapy for pre-melanomas |
| ATE554078T1 (en) | 2007-07-26 | 2012-05-15 | Vitae Pharmaceuticals Inc | SYNTHESIS OF 11-BETA-HYDROXYSTEROID DEHYDROGENASE-1 INHIBITORS |
| TW200927115A (en) | 2007-11-16 | 2009-07-01 | Boehringer Ingelheim Int | Aryl-and heteroarylcarbonyl derivatives of benzomorphanes and related scaffolds, medicaments containing such compounds and their use |
| WO2009075835A1 (en) | 2007-12-11 | 2009-06-18 | Vitae Pharmaceutical, Inc | CYCLIC UREA INHIBITORS OF 11β-HYDROXYSTEROID DEHYDROGENASE 1 |
| TW200934490A (en) | 2008-01-07 | 2009-08-16 | Vitae Pharmaceuticals Inc | Lactam inhibitors of 11 &abgr;-hydroxysteroid dehydrogenase 1 |
| CA2712500A1 (en) | 2008-01-24 | 2009-07-30 | Vitae Pharmaceuticals, Inc. | Cyclic carbazate and semicarbazide inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| US8598160B2 (en) | 2008-02-15 | 2013-12-03 | Vitae Pharmaceuticals, Inc. | Cycloalkyl lactame derivatives as inhibitors of 11-beta-hydroxysteroid dehydrogenase 1 |
| AR071236A1 (en) | 2008-05-01 | 2010-06-02 | Vitae Pharmaceuticals Inc | CYCLE INHIBITORS OF 11BETA-HYDROXIESTEROID DEHYDROGENASE 1 |
| CA2722427A1 (en) | 2008-05-01 | 2009-11-05 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| CA2723034A1 (en) | 2008-05-01 | 2009-11-05 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| US8765780B2 (en) | 2008-05-13 | 2014-07-01 | Boehringer Ingelheim International Gmbh | Alicyclic carboxylic acid derivatives of benzomorphans and related scaffolds, medicaments containing such compounds and their use |
| CA2729998A1 (en) | 2008-07-25 | 2010-01-28 | Boehringer Ingelheim International Gmbh | Inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| PL2324018T3 (en) | 2008-07-25 | 2014-02-28 | Boehringer Ingelheim Int | Cyclic inhibitors of 11 beta-hydroxysteroid dehydrogenase 1 |
| MA33216B1 (en) | 2009-04-30 | 2012-04-02 | Boehringer Ingelheim Int | CYCLIC INHIBITORS OF 11BETA-HYDROXYSTEROID DEHYDROGENASE 1 |
| EP2440537A1 (en) | 2009-06-11 | 2012-04-18 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 based on the 1,3 -oxazinan- 2 -one structure |
| UY33001A (en) | 2009-11-06 | 2011-05-31 | Boehringer Ingelheim Int | ARYL AND HETEROARILCARBONYL HIVAHYDROINDENOPIRIDINE AND OCTAHYDROBENZOQUINOLINE DERIVATIVES |
| WO2011159760A1 (en) | 2010-06-16 | 2011-12-22 | Vitae Pharmaceuticals, Inc. | Substituted 5-,6- and 7-membered heterocycles, medicaments containing such compounds, and their use |
| TWI537258B (en) | 2010-11-05 | 2016-06-11 | 百靈佳殷格翰國際股份有限公司 | Aryl-and heteroarylcarbonyl derivatives of hexahydroindenopyridine and octahydrobenzoquinoline |
| EP2744783A1 (en) | 2011-08-17 | 2014-06-25 | Boehringer Ingelheim International GmbH | Indenopyridine derivatives |
-
1974
- 1974-03-09 DE DE2411382A patent/DE2411382C3/en not_active Expired
-
1975
- 1975-02-28 AT AT153875A patent/AT344332B/en not_active IP Right Cessation
- 1975-03-05 SU SU7502110984A patent/SU577982A3/en active
- 1975-03-05 CH CH280275A patent/CH612425A5/en not_active IP Right Cessation
- 1975-03-06 FI FI750652A patent/FI63571C/en not_active IP Right Cessation
- 1975-03-07 BG BG029183A patent/BG25087A3/en unknown
- 1975-03-07 RO RO7589654A patent/RO70051A/en unknown
- 1975-03-07 BE BE154138A patent/BE826440A/en not_active IP Right Cessation
- 1975-03-07 IL IL46760A patent/IL46760A/en unknown
- 1975-03-07 CA CA221,554A patent/CA1049511A/en not_active Expired
- 1975-03-07 DD DD184642A patent/DD119236A5/xx unknown
- 1975-03-07 RO RO7589653A patent/RO69617A/en unknown
- 1975-03-07 BG BG030538A patent/BG24814A4/en unknown
- 1975-03-07 SE SE7502592A patent/SE421919B/en not_active IP Right Cessation
- 1975-03-07 IE IE505/75A patent/IE40945B1/en unknown
- 1975-03-07 FR FR7507239A patent/FR2262984B1/fr not_active Expired
- 1975-03-07 DK DK92975A patent/DK137188C/en active
- 1975-03-07 NO NO750773A patent/NO141800C/en unknown
- 1975-03-07 BG BG030537A patent/BG24813A4/en unknown
- 1975-03-07 GB GB9633/75A patent/GB1496418A/en not_active Expired
- 1975-03-07 JP JP50027915A patent/JPS5827275B2/en not_active Expired
- 1975-03-07 ZA ZA751394A patent/ZA751394B/en unknown
- 1975-03-07 HU HU75BO1536A patent/HU177408B/en unknown
- 1975-03-07 NL NL7502724A patent/NL7502724A/en not_active Application Discontinuation
- 1975-03-08 PL PL1975178582A patent/PL93499B1/pl unknown
- 1975-03-08 PL PL1975191319A patent/PL93700B1/pl unknown
- 1975-03-08 PL PL1975191318A patent/PL93699B1/pl unknown
- 1975-03-10 PH PH16895A patent/PH14127A/en unknown
- 1975-03-10 CS CS751583A patent/CS188221B2/en unknown
- 1975-08-20 ES ES440348A patent/ES440348A1/en not_active Expired
- 1975-08-20 ES ES440346A patent/ES440346A1/en not_active Expired
- 1975-08-20 ES ES440350A patent/ES440350A1/en not_active Expired
- 1975-08-20 ES ES440345A patent/ES440345A1/en not_active Expired
- 1975-08-20 ES ES440349A patent/ES440349A1/en not_active Expired
- 1975-08-20 ES ES440347A patent/ES440347A1/en not_active Expired
- 1975-12-19 SU SU7502199294A patent/SU577983A3/en active
- 1975-12-19 SU SU752199295A patent/SU588916A3/en active
-
1979
- 1979-04-24 CH CH384779A patent/CH622016A5/en not_active IP Right Cessation
- 1979-04-24 CH CH384579A patent/CH622015A5/en not_active IP Right Cessation
- 1979-04-24 CH CH384379A patent/CH620439A5/en not_active IP Right Cessation
- 1979-04-24 CH CH384879A patent/CH620681A5/en not_active IP Right Cessation
- 1979-04-24 CH CH384479A patent/CH622014A5/en not_active IP Right Cessation
- 1979-04-24 CH CH384979A patent/CH622017A5/en not_active IP Right Cessation
- 1979-04-24 CH CH384679A patent/CH620440A5/en not_active IP Right Cessation
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