GB1092394A - Benzomorphan derivatives and processes for their production - Google Patents
Benzomorphan derivatives and processes for their productionInfo
- Publication number
- GB1092394A GB1092394A GB5150064A GB5150064A GB1092394A GB 1092394 A GB1092394 A GB 1092394A GB 5150064 A GB5150064 A GB 5150064A GB 5150064 A GB5150064 A GB 5150064A GB 1092394 A GB1092394 A GB 1092394A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methoxyethyl
- benzyl
- methyl
- treating
- group
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/82—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Discharge Lamp (AREA)
Abstract
The invention comprises compounds of the formula <FORM:1092394/C2/1> in which R1 represents a hydrogen atom or a hydroxy or a C1- 6 alkanoyloxy group, R2 represents a C1- 6 alkyl, b -methoxyethyl or phenyl group, R3 represents a hydrogen atom or a C1- 6 alkyl group and R4 represents a C1- 6 alkyl or phenyl group; and their preparation by reacting a compound of the formula <FORM:1092394/C2/2> in which R5 represents a hydrogen atom or a C1- 6 alkyl group, with a carbonic acid derivative of the formula halogen-COOR4 and, if desired, alkanoylating a resulting compound in which R1 is an hydroxy group, or hydrolysing a resulting compound in which R1 is an alkanoyloxy group. 2 - Methyl - 5 - (b - methoxyethyl) - 6,7 - benzomorphan and its hydrochloride are obtained by cyclization of 2-benzyl-4-(b -methoxyethyl)-1,2, 5,6-tetrahydropyridine with aluminium tribromide followed by salification. 2 - Benzyl - 4 - (b - methoxyethyl) - 1,2,5,6-tetrahydropyridine is obtained by (a) reacting 4-(b -methoxyethyl)-pyridine with methyl iodide to form 4-(b -methoxyethyl)-pyridine methiodide, treating this with sodium borohydride to form 1 - methyl - 4 - (b - methoxyethyl) - 1,2,5,6 - tetrahydropyridine, treating this with benzyl chloride to form 1-benzyl-1-methyl-4-(b -methoxyethyl)-1,2, 5,6-tetrahydropyridinium chloride and treating this with phenyl lithium, or (b) reacting 4 (b -methoxyethyl)-pyridine methiodide with benzyl magnesium chloride and treating the product with aqueous ammonium chloride to form 2-benzyl - 4 - (b - methoxyethyl) - 1 - methyl - 1,2-dihydropyridine and hydrogenating this with sodium borohydride. Pharmaceutical compositions having analgesic, antitussive and morphine antagonistic activity, for oral or parenteral administration, comprise a compound of the invention together with a pharmaceutical carrier.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33229663A | 1963-12-20 | 1963-12-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1092394A true GB1092394A (en) | 1967-11-22 |
Family
ID=23297612
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5149864A Expired GB1077711A (en) | 1963-12-20 | 1964-12-18 | Benzomorphans and process for their preparation |
| GB5150064A Expired GB1092394A (en) | 1963-12-20 | 1964-12-18 | Benzomorphan derivatives and processes for their production |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5149864A Expired GB1077711A (en) | 1963-12-20 | 1964-12-18 | Benzomorphans and process for their preparation |
Country Status (12)
| Country | Link |
|---|---|
| AT (4) | AT261126B (en) |
| BE (2) | BE657405A (en) |
| CH (7) | CH449641A (en) |
| DE (2) | DE1445853A1 (en) |
| DK (4) | DK108497C (en) |
| ES (4) | ES307302A1 (en) |
| FR (2) | FR4346M (en) |
| GB (2) | GB1077711A (en) |
| IL (2) | IL22643A (en) |
| NL (3) | NL6414820A (en) |
| NO (2) | NO119273B (en) |
| SE (2) | SE305657B (en) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7501433B2 (en) | 2002-05-17 | 2009-03-10 | Jenken Biosciences, Inc. | Opioid and opioid-like compounds and uses thereof |
| WO2003097608A2 (en) | 2002-05-17 | 2003-11-27 | Jenken Biosciences, Inc. | Opioid and opioid-like compounds and uses thereof |
| US7923454B2 (en) | 2002-05-17 | 2011-04-12 | Jenken Biosciences, Inc. | Opioid and opioid-like compounds and uses thereof |
| US8017622B2 (en) | 2003-05-16 | 2011-09-13 | Jenken Biosciences, Inc. | Opioid and opioid-like compounds and uses thereof |
| US8835426B2 (en) | 2007-02-26 | 2014-09-16 | Vitae Pharmaceuticals, Inc. | Cyclic urea and carbamate inhibitors of 11β-hydroxysteroid dehydrogenase 1 |
| ES2395081T3 (en) | 2007-07-26 | 2013-02-08 | Vitae Pharmaceuticals, Inc. | Synthesis of 11 beta-hydroxysteroid dehydrogenase inhibitors type 1 |
| AR069207A1 (en) | 2007-11-07 | 2010-01-06 | Vitae Pharmaceuticals Inc | CYCLIC UREAS AS INHIBITORS OF THE 11 BETA - HIDROXI-ESTEROIDE DESHIDROGENASA 1 |
| 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 |
| EP2229368A1 (en) | 2007-12-11 | 2010-09-22 | Vitae Pharmaceuticals, Inc. | Cyclic urea inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| TW200934490A (en) | 2008-01-07 | 2009-08-16 | Vitae Pharmaceuticals Inc | Lactam inhibitors of 11 &abgr;-hydroxysteroid dehydrogenase 1 |
| JP5490020B2 (en) | 2008-01-24 | 2014-05-14 | ヴァイティー ファーマシューティカルズ，インコーポレイテッド | Cyclic carbazate and semicarbazide inhibitors of 11β-hydroxysteroid dehydrogenase 1 |
| EP2252598A2 (en) | 2008-02-11 | 2010-11-24 | Vitae Pharmaceuticals, Inc. | 1,3-oxazepan-2-one and 1,3-diazepan-2-one inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| ATE531696T1 (en) * | 2008-02-12 | 2011-11-15 | Boehringer Ingelheim Int | UREA DERIVATIVES OF BENZOMORPHANES, CORRESPONDING SCAFFOLDS, MEDICATIONS CONTAINING SUCH COMPOUNDS AND THEIR USE |
| WO2009102460A2 (en) | 2008-02-15 | 2009-08-20 | Vitae Pharmaceuticals, Inc. | Inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| EP2291370B1 (en) | 2008-05-01 | 2013-11-27 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| CL2009001058A1 (en) | 2008-05-01 | 2010-09-10 | Vitae Pharmaceuticals Inc | Compounds derived from substituted oxazines, inhibitors of 11b-hydroxysteroid dehydrogenase type-1; pharmaceutical composition; and use of the compound to inhibit the activity of 11b-hsd1, as in the treatment of diabetes, dyslipidemia, hypertension, obesity, cancer, glaucoma, among others. |
| JP5451752B2 (en) | 2008-05-01 | 2014-03-26 | ヴァイティー ファーマシューティカルズ，インコーポレイテッド | Cyclic inhibitor of 11β-hydroxysteroid dehydrogenase 1 |
| WO2009134400A1 (en) | 2008-05-01 | 2009-11-05 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| EP2288596B1 (en) | 2008-05-13 | 2016-11-30 | 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 |
| CA2730499A1 (en) | 2008-07-25 | 2010-01-28 | Boehringer Ingelheim International Gmbh | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| WO2010046445A2 (en) | 2008-10-23 | 2010-04-29 | Boehringer Ingelheim International Gmbh | Urea derivatives of substituted nortropanes, medicaments containing such compounds and their use |
| US8637505B2 (en) | 2009-02-04 | 2014-01-28 | Boehringer Ingelheim International Gmbh | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| MA33216B1 (en) | 2009-04-30 | 2012-04-02 | Boehringer Ingelheim Int | CYCLIC INHIBITORS OF 11BETA-HYDROXYSTEROID DEHYDROGENASE 1 |
| WO2010139673A1 (en) | 2009-06-02 | 2010-12-09 | Boehringer Ingelheim International Gmbh | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| WO2011011123A1 (en) | 2009-06-11 | 2011-01-27 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 based on the 1,3 -oxazinan- 2 -one structure |
| US8883778B2 (en) | 2009-07-01 | 2014-11-11 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11 beta-hydroxysteroid dehydrogenase 1 |
| UY33001A (en) | 2009-11-06 | 2011-05-31 | Boehringer Ingelheim Int | ARYL AND HETEROARILCARBONYL HIVAHYDROINDENOPIRIDINE AND OCTAHYDROBENZOQUINOLINE DERIVATIVES |
| JP5860042B2 (en) | 2010-06-16 | 2016-02-16 | ヴァイティー ファーマシューティカルズ，インコーポレイテッド | Substituted 5, 6 and 7 membered heterocycles, medicaments containing such compounds and their use |
| EP2585444B1 (en) | 2010-06-25 | 2014-10-22 | Boehringer Ingelheim International GmbH | Azaspirohexanones as inhibitors of 11-beta-hsd1 for the treatment of metabolic disorders |
| EP2635268A1 (en) | 2010-11-02 | 2013-09-11 | Boehringer Ingelheim International GmbH | Pharmaceutical combinations for the treatment of metabolic disorders |
| 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 |
| JP2014524438A (en) | 2011-08-17 | 2014-09-22 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Indenopyridine derivatives |
-
0
- NL NL127995D patent/NL127995C/xx active
-
1964
- 1964-11-30 CH CH1618967A patent/CH449641A/en unknown
- 1964-11-30 CH CH1619167A patent/CH449643A/en unknown
- 1964-11-30 CH CH1618867A patent/CH449640A/en unknown
- 1964-11-30 CH CH1618767A patent/CH449639A/en unknown
- 1964-11-30 CH CH1538464A patent/CH446371A/en unknown
- 1964-11-30 CH CH1538364A patent/CH448118A/en unknown
- 1964-11-30 CH CH1619067A patent/CH449642A/en unknown
- 1964-12-18 DE DE19641445853 patent/DE1445853A1/en active Pending
- 1964-12-18 AT AT1074264A patent/AT261126B/en active
- 1964-12-18 DE DE19641445854 patent/DE1445854A1/en active Pending
- 1964-12-18 GB GB5149864A patent/GB1077711A/en not_active Expired
- 1964-12-18 SE SE1536164A patent/SE305657B/xx unknown
- 1964-12-18 IL IL2264364A patent/IL22643A/en unknown
- 1964-12-18 GB GB5150064A patent/GB1092394A/en not_active Expired
- 1964-12-18 AT AT392965A patent/AT249277B/en active
- 1964-12-18 NL NL6414820A patent/NL6414820A/xx unknown
- 1964-12-18 AT AT1074364A patent/AT253687B/en active
- 1964-12-18 IL IL2264264A patent/IL22642A/en unknown
- 1964-12-18 NL NL6414821A patent/NL6414821A/xx unknown
- 1964-12-18 SE SE1536064A patent/SE322779B/xx unknown
- 1964-12-18 AT AT392865A patent/AT249276B/en active
- 1964-12-19 NO NO15606264A patent/NO119273B/no unknown
- 1964-12-19 ES ES0307302A patent/ES307302A1/en not_active Expired
- 1964-12-19 DK DK429865A patent/DK108497C/en active
- 1964-12-19 ES ES0307301A patent/ES307301A1/en not_active Expired
- 1964-12-19 DK DK626864A patent/DK106552C/en active
- 1964-12-19 NO NO15606364A patent/NO119274B/no unknown
- 1964-12-19 DK DK626764A patent/DK108495C/en active
- 1964-12-19 DK DK429765A patent/DK108496C/en active
- 1964-12-19 ES ES0307299A patent/ES307299A1/en not_active Expired
- 1964-12-19 ES ES0307300A patent/ES307300A1/en not_active Expired
- 1964-12-21 BE BE657405D patent/BE657405A/xx unknown
- 1964-12-21 BE BE657406D patent/BE657406A/xx unknown
-
1965
- 1965-03-19 FR FR9866A patent/FR4346M/fr active Active
- 1965-03-19 FR FR9865A patent/FR4345M/fr active Active
Also Published As
| Publication number | Publication date |
|---|---|
| NL6414821A (en) | 1965-06-21 |
| AT249277B (en) | 1966-09-12 |
| IL22643A (en) | 1968-07-25 |
| CH449641A (en) | 1968-01-15 |
| GB1077711A (en) | 1967-08-02 |
| BE657406A (en) | 1965-06-21 |
| SE322779B (en) | 1970-04-20 |
| ES307301A1 (en) | 1965-05-16 |
| CH448118A (en) | 1967-12-15 |
| DK108496C (en) | 1967-12-27 |
| CH449640A (en) | 1968-01-15 |
| SE305657B (en) | 1968-11-04 |
| FR4345M (en) | 1966-08-16 |
| CH446371A (en) | 1967-11-15 |
| AT261126B (en) | 1968-04-10 |
| BE657405A (en) | 1965-06-21 |
| DK108497C (en) | 1967-12-27 |
| DE1445854A1 (en) | 1968-12-05 |
| NL6414820A (en) | 1965-06-21 |
| DK106552C (en) | 1967-02-20 |
| IL22642A (en) | 1968-07-25 |
| NO119273B (en) | 1970-04-27 |
| NO119274B (en) | 1970-04-27 |
| CH449642A (en) | 1968-01-15 |
| FR4346M (en) | 1966-08-16 |
| ES307299A1 (en) | 1965-05-16 |
| AT253687B (en) | 1967-04-25 |
| NL127995C (en) | |
| ES307300A1 (en) | 1965-05-01 |
| CH449643A (en) | 1968-01-15 |
| CH449639A (en) | 1968-01-15 |
| AT249276B (en) | 1966-09-12 |
| ES307302A1 (en) | 1965-05-16 |
| DE1445853A1 (en) | 1968-12-05 |
| DK108495C (en) | 1967-12-27 |
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