FI57261C - Foerfarande foer framstaellning av pao centralnervsystemet verkande n-(heteroaryl-metyl)-6,14-endoeteno/endoetano-7alfa-hydroxylalkyltetrahydronororipavin och -tebain och deras syraadditionssalter - Google Patents
Foerfarande foer framstaellning av pao centralnervsystemet verkande n-(heteroaryl-metyl)-6,14-endoeteno/endoetano-7alfa-hydroxylalkyltetrahydronororipavin och -tebain och deras syraadditionssalter Download PDFInfo
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- FI57261C FI57261C FI1989/73A FI198973A FI57261C FI 57261 C FI57261 C FI 57261C FI 1989/73 A FI1989/73 A FI 1989/73A FI 198973 A FI198973 A FI 198973A FI 57261 C FI57261 C FI 57261C
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- formula
- methyl
- tetrahydro
- compound
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Links
- 238000000034 method Methods 0.000 claims description 167
- -1 lithium aluminum hydride Chemical compound 0.000 claims description 141
- 150000001875 compounds Chemical class 0.000 claims description 134
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- 238000002844 melting Methods 0.000 claims description 47
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 18
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- 239000001257 hydrogen Substances 0.000 claims description 17
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- 239000012280 lithium aluminium hydride Substances 0.000 claims description 16
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
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- FQXXSQDCDRQNQE-UHFFFAOYSA-N markiertes Thebain Natural products COC1=CC=C2C(N(CC3)C)CC4=CC=C(OC)C5=C4C23C1O5 FQXXSQDCDRQNQE-UHFFFAOYSA-N 0.000 claims description 4
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
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- 125000005208 trialkylammonium group Chemical group 0.000 claims description 3
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 3
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- 238000009472 formulation Methods 0.000 claims 1
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- 150000002367 halogens Chemical class 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
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- 238000007796 conventional method Methods 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- 238000005661 deetherification reaction Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 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
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 230000008707 rearrangement Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical class C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/09—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems
- C07D489/10—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems with a bridge between positions 6 and 14
- C07D489/12—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems with a bridge between positions 6 and 14 the bridge containing only two carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
-
- 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
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/02—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2230154A DE2230154A1 (de) | 1972-06-21 | 1972-06-21 | N-(heteroaryl-methyl)-6,14-endoaetheno7alpha-hydroxyalkyl-tetrahydro-nororipavine und -thebaine, deren hydrierungsprodukte und saeureadditionssalze sowie verfahren zu deren herstellung |
| DE2230154 | 1972-06-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI57261B FI57261B (fi) | 1980-03-31 |
| FI57261C true FI57261C (fi) | 1980-07-10 |
Family
ID=5848276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI1989/73A FI57261C (fi) | 1972-06-21 | 1973-06-20 | Foerfarande foer framstaellning av pao centralnervsystemet verkande n-(heteroaryl-metyl)-6,14-endoeteno/endoetano-7alfa-hydroxylalkyltetrahydronororipavin och -tebain och deras syraadditionssalter |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3931189A (en, 2012) |
| JP (1) | JPS5614673B2 (en, 2012) |
| AT (7) | AT328098B (en, 2012) |
| BE (1) | BE801271A (en, 2012) |
| CH (7) | CH587264A5 (en, 2012) |
| DE (1) | DE2230154A1 (en, 2012) |
| DK (1) | DK141629C (en, 2012) |
| ES (3) | ES416106A1 (en, 2012) |
| FI (1) | FI57261C (en, 2012) |
| FR (1) | FR2189066B1 (en, 2012) |
| GB (1) | GB1431385A (en, 2012) |
| NL (1) | NL7308555A (en, 2012) |
| NO (1) | NO139050C (en, 2012) |
| SE (1) | SE412235B (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4232026A (en) * | 1978-07-20 | 1980-11-04 | Merck & Co., Inc. | Diazaditwistanes, and pharmaceutical compositions for treating pain in warm blooded animals containing them |
| JPS62298530A (ja) * | 1986-06-16 | 1987-12-25 | Otsuka Pharmaceut Co Ltd | 坐薬用医薬組成物 |
| CN1233645C (zh) * | 2001-09-14 | 2005-12-28 | 中国人民解放军军事医学科学院毒物药物研究所 | 新的东罂粟碱衍生物及其医药用途 |
| CN1939920B (zh) * | 2005-09-29 | 2011-08-31 | 中国人民解放军军事医学科学院毒物药物研究所 | 东罂粟碱类化合物及其医药用途 |
| CN103450206A (zh) | 2008-07-30 | 2013-12-18 | 普渡制药公司 | 丁丙诺啡类似物 |
| JP2021104932A (ja) * | 2018-03-30 | 2021-07-26 | 日本ケミファ株式会社 | モルヒナン誘導体の製造方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3474101A (en) * | 1960-09-05 | 1969-10-21 | Reckitt & Sons Ltd | Thebaine and oripavine derivatives |
| US3285914A (en) * | 1964-06-11 | 1966-11-15 | Smith Kline French Lab | 3-n-substituted derivatives of oripavine and thebaine |
| GB1136764A (en) * | 1965-08-13 | 1968-12-18 | Reckitt & Sons Ltd | Derivatives of thebaine and oripavine |
| GB1146272A (en) * | 1966-01-17 | 1969-03-26 | Reckitt & Sons Ltd | Novel thebaine and oripavine derivatives |
| GB1223445A (en) * | 1968-07-18 | 1971-02-24 | Reckitt & Colmann Prod Ltd | Improvements in or relating to derivatives of morphine, their salts, and processes for their preparation |
| DE2107989A1 (de) * | 1971-02-19 | 1972-09-07 | Boehringer Sohn Ingelheim | N-(Furyl-methy])-morphinane, deren Säureadditionssalze sowie Verfahren zu deren Herstellung |
-
1972
- 1972-06-21 DE DE2230154A patent/DE2230154A1/de not_active Withdrawn
-
1973
- 1973-06-06 AT AT461874*7A patent/AT328098B/de not_active IP Right Cessation
- 1973-06-06 AT AT462174*7A patent/AT328101B/de not_active IP Right Cessation
- 1973-06-06 AT AT462074*7A patent/AT328100B/de not_active IP Right Cessation
- 1973-06-06 AT AT494473A patent/AT325219B/de not_active IP Right Cessation
- 1973-06-06 AT AT461974*7A patent/AT328099B/de not_active IP Right Cessation
- 1973-06-06 AT AT462374*7A patent/AT329198B/de not_active IP Right Cessation
- 1973-06-06 AT AT462274*7A patent/AT327409B/de not_active IP Right Cessation
- 1973-06-13 US US05/369,500 patent/US3931189A/en not_active Expired - Lifetime
- 1973-06-18 CH CH1460676A patent/CH587264A5/xx not_active IP Right Cessation
- 1973-06-18 CH CH1460976A patent/CH585752A5/xx not_active IP Right Cessation
- 1973-06-18 CH CH1460776A patent/CH586224A5/xx not_active IP Right Cessation
- 1973-06-18 CH CH1460876A patent/CH594672A5/xx not_active IP Right Cessation
- 1973-06-18 CH CH881573A patent/CH585751A5/xx not_active IP Right Cessation
- 1973-06-18 CH CH1461176A patent/CH594673A5/xx not_active IP Right Cessation
- 1973-06-18 CH CH1461076A patent/CH585753A5/xx not_active IP Right Cessation
- 1973-06-20 NL NL7308555A patent/NL7308555A/xx not_active Application Discontinuation
- 1973-06-20 DK DK341273A patent/DK141629C/da active
- 1973-06-20 ES ES416106A patent/ES416106A1/es not_active Expired
- 1973-06-20 NO NO2561/73A patent/NO139050C/no unknown
- 1973-06-20 SE SE7308709A patent/SE412235B/xx unknown
- 1973-06-20 FI FI1989/73A patent/FI57261C/fi active
- 1973-06-20 GB GB2934673A patent/GB1431385A/en not_active Expired
- 1973-06-20 JP JP6969173A patent/JPS5614673B2/ja not_active Expired
- 1973-06-21 FR FR7322738A patent/FR2189066B1/fr not_active Expired
- 1973-06-21 BE BE132576A patent/BE801271A/xx unknown
-
1974
- 1974-04-05 ES ES425015A patent/ES425015A1/es not_active Expired
- 1974-04-05 ES ES425010A patent/ES425010A1/es not_active Expired
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