ES453485A1 - 2,5-dimethyl-thieno(2,3-f)morphane and a process for obtaining it - Google Patents
2,5-dimethyl-thieno(2,3-f)morphane and a process for obtaining itInfo
- Publication number
- ES453485A1 ES453485A1 ES453485A ES453485A ES453485A1 ES 453485 A1 ES453485 A1 ES 453485A1 ES 453485 A ES453485 A ES 453485A ES 453485 A ES453485 A ES 453485A ES 453485 A1 ES453485 A1 ES 453485A1
- Authority
- ES
- Spain
- Prior art keywords
- dimethyl
- thieno
- formula
- obtaining
- reacted
- 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
- 238000000034 method Methods 0.000 title abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 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 2
- YOBTXORLVXZWSR-UHFFFAOYSA-M 1,4-dimethylpyridin-1-ium;iodide Chemical compound [I-].CC1=CC=[N+](C)C=C1 YOBTXORLVXZWSR-UHFFFAOYSA-M 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
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- SUEXIXRFSURADT-NEWATCJESA-N CC1N[C@H]2[C@@H]3CC4=C(C[C@@]3(C=3C=C(C=CC=3C2)C)C1)SC=C4 Chemical compound CC1N[C@H]2[C@@H]3CC4=C(C[C@@]3(C=3C=C(C=CC=3C2)C)C1)SC=C4 SUEXIXRFSURADT-NEWATCJESA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000010790 dilution Methods 0.000 abstract 1
- 239000012895 dilution Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229960005181 morphine Drugs 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- -1 sodium boron tetrahydride Chemical compound 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 125000004853 tetrahydropyridinyl group Chemical class N1(CCCC=C1)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/08—Bridged systems
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
A process for obtaining 2,5-dimethyl-thieno [2,3-f] morphinan of the formula (I). ** (see formula) ** Characterized in that in its first synthesis stage the 3-tenylmagnesium bromide obtained under high dilution conditions and under inert atmosphere is reacted with the 1,4-dimethylpyridinium iodide in anhydrous ether maintained at the reflux temperature, whereby the intermediate 2- (3-tenyl) -1,4-dimethyl-1,2-dihydropyridine is obtained, which without further purification is reacted in basic medium, for example sodium hydroxide, with sodium boron tetrahydride. In aqueous-methanolic solution, leading to a mixture of tetrahydropyridines, which is then heated to 135ºC in the presence of an acid, for example hydrobromic acid, whereby 2,5-dimethyl-thieno [2,34-f] is obtained ] morphine of the formula (I). (Machine-translation by Google Translate, not legally binding)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES453485A ES453485A1 (en) | 1976-11-19 | 1976-11-19 | 2,5-dimethyl-thieno(2,3-f)morphane and a process for obtaining it |
| DE2750197A DE2750197C3 (en) | 1976-11-19 | 1977-11-10 | 43,6,7,8,9-Hexahydro-5,9-methane-6,9-dimethylthieno [3,2, -d] azocine and process for its preparation |
| AR269962A AR214761A1 (en) | 1976-11-19 | 1977-11-14 | A PROCEDURE FOR THE OBTAINING OF 2,5-DIMETHYL-HAVE (2,3-F) MORPHANE |
| GB47719/77A GB1574514A (en) | 1976-11-19 | 1977-11-16 | 2,5-dimethyl-thieno(2,3-f)morphane and a process for obtaining it |
| AT828177A AT353430B (en) | 1976-11-19 | 1977-11-18 | PROCESS FOR PREPARING THE NEW 2,5- -DIMETHYL-THIENO (2,3-F) MORPHANE |
| FR7734751A FR2371452A1 (en) | 1976-11-19 | 1977-11-18 | 2,5-DIMETHYL-THIENO (2-3-F) MORPHANE, ITS PREPARATION PROCESS AND ITS APPLICATIONS AS A MEDICINAL PRODUCT |
| PT67297A PT67297B (en) | 1976-11-19 | 1977-11-18 | Process for the preparation of 2,5-dimethyl-tiene/2,3-f/morphane |
| JP13798577A JPS5365898A (en) | 1976-11-19 | 1977-11-18 | Novel 2*55dimethyllthien*2*33f* morphane and process for preparing same |
| BE182733A BE860963A (en) | 1976-11-19 | 1977-11-18 | 2,5-DIMETHYL-THIENO (2-3-F) MORPHANE, ITS PREPARATION PROCESS AND ITS APPLICATIONS AS A MEDICINAL PRODUCT |
| NL7712770A NL7712770A (en) | 1976-11-19 | 1977-11-18 | 2,5-DIMETHYL-THIEEN- (2,3-F) -MORPHANE. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES453485A ES453485A1 (en) | 1976-11-19 | 1976-11-19 | 2,5-dimethyl-thieno(2,3-f)morphane and a process for obtaining it |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES453485A1 true ES453485A1 (en) | 1977-11-16 |
Family
ID=8472620
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES453485A Expired ES453485A1 (en) | 1976-11-19 | 1976-11-19 | 2,5-dimethyl-thieno(2,3-f)morphane and a process for obtaining it |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5365898A (en) |
| AR (1) | AR214761A1 (en) |
| AT (1) | AT353430B (en) |
| BE (1) | BE860963A (en) |
| DE (1) | DE2750197C3 (en) |
| ES (1) | ES453485A1 (en) |
| FR (1) | FR2371452A1 (en) |
| GB (1) | GB1574514A (en) |
| NL (1) | NL7712770A (en) |
| PT (1) | PT67297B (en) |
-
1976
- 1976-11-19 ES ES453485A patent/ES453485A1/en not_active Expired
-
1977
- 1977-11-10 DE DE2750197A patent/DE2750197C3/en not_active Expired
- 1977-11-14 AR AR269962A patent/AR214761A1/en active
- 1977-11-16 GB GB47719/77A patent/GB1574514A/en not_active Expired
- 1977-11-18 BE BE182733A patent/BE860963A/en unknown
- 1977-11-18 NL NL7712770A patent/NL7712770A/en not_active Application Discontinuation
- 1977-11-18 AT AT828177A patent/AT353430B/en not_active IP Right Cessation
- 1977-11-18 FR FR7734751A patent/FR2371452A1/en not_active Withdrawn
- 1977-11-18 PT PT67297A patent/PT67297B/en unknown
- 1977-11-18 JP JP13798577A patent/JPS5365898A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1574514A (en) | 1980-09-10 |
| PT67297B (en) | 1979-04-20 |
| DE2750197C3 (en) | 1980-09-18 |
| DE2750197A1 (en) | 1978-05-24 |
| DE2750197B2 (en) | 1980-01-24 |
| NL7712770A (en) | 1978-05-23 |
| ATA828177A (en) | 1979-04-15 |
| FR2371452A1 (en) | 1978-06-16 |
| BE860963A (en) | 1978-03-16 |
| AR214761A1 (en) | 1979-07-31 |
| JPS5365898A (en) | 1978-06-12 |
| PT67297A (en) | 1977-12-01 |
| AT353430B (en) | 1979-11-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 19981103 |