SE430160B - Forfarande for framstellning av 2?721-hydroxi-2-(5-isoxazolylmetyl)-6,7-bensomorfaner och deras syraadditionssalter - Google Patents
Forfarande for framstellning av 2?721-hydroxi-2-(5-isoxazolylmetyl)-6,7-bensomorfaner och deras syraadditionssalterInfo
- Publication number
- SE430160B SE430160B SE7804260A SE7804260A SE430160B SE 430160 B SE430160 B SE 430160B SE 7804260 A SE7804260 A SE 7804260A SE 7804260 A SE7804260 A SE 7804260A SE 430160 B SE430160 B SE 430160B
- Authority
- SE
- Sweden
- Prior art keywords
- hydroxy
- isoxazolylmethyl
- benzomorphan
- formula
- acid
- Prior art date
Links
- -1 5-ISOXAZOLYLMETHYL Chemical class 0.000 title claims description 46
- 239000002253 acid Substances 0.000 title claims description 20
- 150000003839 salts Chemical class 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
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- 125000005843 halogen group Chemical group 0.000 claims description 2
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
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- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
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- 230000002452 interceptive effect Effects 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229940099690 malic acid Drugs 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- VOKSWYLNZZRQPF-GDIGMMSISA-N pentazocine Chemical compound C1C2=CC=C(O)C=C2[C@@]2(C)[C@@H](C)[C@@H]1N(CC=C(C)C)CC2 VOKSWYLNZZRQPF-GDIGMMSISA-N 0.000 description 1
- 229960005301 pentazocine Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- UGKSITLWMZJTHC-UHFFFAOYSA-N tribromo-$l^{3}-bromane Chemical compound BrBr(Br)Br UGKSITLWMZJTHC-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/02—Suppositories; Bougies; Bases therefor; Ovules
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/08—Solutions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/286—Polysaccharides, e.g. gums; Cyclodextrin
-
- 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)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Dermatology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- General Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772716687 DE2716687A1 (de) | 1977-04-15 | 1977-04-15 | 2'-hydroxy-2-(5-isoxazolylmethyl)-6,7benzomorphane, deren saeureadditionssalze und diese enthaltende arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7804260L SE7804260L (sv) | 1978-10-16 |
| SE430160B true SE430160B (sv) | 1983-10-24 |
Family
ID=6006359
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7804260A SE430160B (sv) | 1977-04-15 | 1978-04-14 | Forfarande for framstellning av 2?721-hydroxi-2-(5-isoxazolylmetyl)-6,7-bensomorfaner och deras syraadditionssalter |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4133888A (xx) |
| JP (1) | JPS53130671A (xx) |
| AT (3) | AT358192B (xx) |
| AU (1) | AU514938B2 (xx) |
| BE (1) | BE866013A (xx) |
| CA (1) | CA1079726A (xx) |
| CH (1) | CH638519A5 (xx) |
| DE (1) | DE2716687A1 (xx) |
| DK (1) | DK144678C (xx) |
| ES (3) | ES468798A1 (xx) |
| FI (1) | FI63399C (xx) |
| FR (1) | FR2387228A1 (xx) |
| GB (1) | GB1575156A (xx) |
| GR (1) | GR64819B (xx) |
| IE (1) | IE46722B1 (xx) |
| IL (1) | IL54509A (xx) |
| IT (1) | IT1102595B (xx) |
| LU (1) | LU79430A1 (xx) |
| NL (1) | NL7803977A (xx) |
| NO (1) | NO148418C (xx) |
| NZ (1) | NZ186971A (xx) |
| PH (1) | PH13854A (xx) |
| PT (1) | PT67907B (xx) |
| SE (1) | SE430160B (xx) |
| ZA (1) | ZA782149B (xx) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1575009A (en) * | 1976-06-21 | 1980-09-17 | Acf Chemiefarma Nv | 6,7-benzomorphan derivatives |
| NL7907800A (nl) | 1979-10-23 | 1981-04-27 | Acf Chemiefarma Nv | Nieuwe 6,7-benzomorfanderivaten en zuuradditiezouten daarvan, farmaceutische preparaten die een dergelijke verbinding bevatten, alsmede werkwijze voor het bereiden van deze verbindingen en de farmaceutische preparaten. |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3499906A (en) * | 1966-05-20 | 1970-03-10 | Merck & Co Inc | 5,9-diethyl-2'-hydroxy-2-substituted-6,7-benzomorphans |
| CS166802B2 (xx) * | 1971-02-08 | 1976-03-29 | Boehringer Sohn Ingelheim | |
| US3853889A (en) * | 1973-07-18 | 1974-12-10 | Bristol Myers Co | 3,14-substituted-8-oxamorphinans |
| DE2411382C3 (de) * | 1974-03-09 | 1979-09-06 | C.H. Boehringer Sohn, 6507 Ingelheim | 2-Tetrahydrofurfuryl-6,7-benzomorphane, Verfahren zur Herstellung und deren Verwendung |
| DE2437610A1 (de) * | 1974-08-05 | 1976-02-26 | Boehringer Sohn Ingelheim | Neue 5,9-beta-disubstituierte 2-tetrahydrofurfuryl-6,7-benzomorphane, deren saeureadditionssalze, ihre verwendung als arzneimittel und verfahren zu deren herstellung |
-
1977
- 1977-04-15 DE DE19772716687 patent/DE2716687A1/de not_active Ceased
-
1978
- 1978-04-04 FI FI781025A patent/FI63399C/fi not_active IP Right Cessation
- 1978-04-06 AT AT241978A patent/AT358192B/de not_active IP Right Cessation
- 1978-04-06 GR GR55915A patent/GR64819B/el unknown
- 1978-04-12 CH CH394078A patent/CH638519A5/de not_active IP Right Cessation
- 1978-04-12 US US05/895,631 patent/US4133888A/en not_active Expired - Lifetime
- 1978-04-13 LU LU79430A patent/LU79430A1/de unknown
- 1978-04-13 IT IT48887/78A patent/IT1102595B/it active
- 1978-04-14 NO NO781310A patent/NO148418C/no unknown
- 1978-04-14 DK DK163578A patent/DK144678C/da not_active IP Right Cessation
- 1978-04-14 PT PT67907A patent/PT67907B/pt unknown
- 1978-04-14 IL IL54509A patent/IL54509A/xx unknown
- 1978-04-14 NL NL7803977A patent/NL7803977A/xx not_active Application Discontinuation
- 1978-04-14 ES ES468798A patent/ES468798A1/es not_active Expired
- 1978-04-14 PH PH21010A patent/PH13854A/en unknown
- 1978-04-14 NZ NZ186971A patent/NZ186971A/xx unknown
- 1978-04-14 GB GB14796/78A patent/GB1575156A/en not_active Expired
- 1978-04-14 JP JP4409178A patent/JPS53130671A/ja active Pending
- 1978-04-14 SE SE7804260A patent/SE430160B/sv not_active IP Right Cessation
- 1978-04-14 IE IE742/78A patent/IE46722B1/en unknown
- 1978-04-14 AU AU35098/78A patent/AU514938B2/en not_active Expired
- 1978-04-14 FR FR7811110A patent/FR2387228A1/fr active Granted
- 1978-04-14 CA CA301,198A patent/CA1079726A/en not_active Expired
- 1978-04-14 BE BE186818A patent/BE866013A/xx not_active IP Right Cessation
- 1978-04-14 ZA ZA00782149A patent/ZA782149B/xx unknown
- 1978-08-07 ES ES472408A patent/ES472408A1/es not_active Expired
- 1978-08-07 ES ES472407A patent/ES472407A1/es not_active Expired
-
1979
- 1979-08-14 AT AT552079A patent/AT360667B/de not_active IP Right Cessation
- 1979-08-14 AT AT551979A patent/AT360666B/de not_active IP Right Cessation
Also Published As
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| NUG | Patent has lapsed |
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