FI56835C - Foerfarande foer framstaellning av farmakologiskt vaerdefulla 6,7-benzomorfanderivat - Google Patents
Foerfarande foer framstaellning av farmakologiskt vaerdefulla 6,7-benzomorfanderivat Download PDFInfo
- Publication number
- FI56835C FI56835C FI972/74A FI97274A FI56835C FI 56835 C FI56835 C FI 56835C FI 972/74 A FI972/74 A FI 972/74A FI 97274 A FI97274 A FI 97274A FI 56835 C FI56835 C FI 56835C
- Authority
- FI
- Finland
- Prior art keywords
- group
- formula
- compound
- defined above
- benzomorphane
- Prior art date
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- 230000000144 pharmacologic effect Effects 0.000 title claims 2
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- 150000001875 compounds Chemical class 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
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- 125000005843 halogen group Chemical group 0.000 claims description 5
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- 125000001424 substituent group Chemical group 0.000 claims description 5
- 230000010933 acylation Effects 0.000 claims description 4
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- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- 230000002354 daily effect Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229950006191 gluconic acid Drugs 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- XYKIUTSFQGXHOW-UHFFFAOYSA-N propan-2-one;toluene Chemical compound CC(C)=O.CC1=CC=CC=C1 XYKIUTSFQGXHOW-UHFFFAOYSA-N 0.000 description 1
- XERZRCSNXUVIIT-UHFFFAOYSA-N propanoyl 4-fluorobenzoate Chemical compound CCC(=O)OC(=O)C1=CC=C(F)C=C1 XERZRCSNXUVIIT-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 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
- 230000009257 reactivity Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3733373 | 1973-03-31 | ||
| JP48037333A JPS5817190B2 (ja) | 1973-03-31 | 1973-03-31 | シンキナ ４，５− ジアルキルベンゾモルフアンユウドウタイノセイホウ |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI56835B FI56835B (fi) | 1979-12-31 |
| FI56835C true FI56835C (fi) | 1980-04-10 |
Family
ID=12494691
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI972/74A FI56835C (fi) | 1973-03-31 | 1974-03-29 | Foerfarande foer framstaellning av farmakologiskt vaerdefulla 6,7-benzomorfanderivat |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3961066A (cs) |
| JP (1) | JPS5817190B2 (cs) |
| AT (1) | AT335630B (cs) |
| AU (1) | AU475932B2 (cs) |
| BE (1) | BE813096A (cs) |
| CA (1) | CA1040629A (cs) |
| CH (1) | CH594628A5 (cs) |
| CS (1) | CS183732B2 (cs) |
| DE (1) | DE2415124A1 (cs) |
| ES (1) | ES424787A1 (cs) |
| FI (1) | FI56835C (cs) |
| FR (1) | FR2223043B1 (cs) |
| GB (1) | GB1460053A (cs) |
| HU (1) | HU169133B (cs) |
| NL (1) | NL7404411A (cs) |
| NO (1) | NO142713C (cs) |
| SE (1) | SE413025B (cs) |
| SU (1) | SU591141A3 (cs) |
| ZA (1) | ZA742013B (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4205171A (en) * | 1976-01-12 | 1980-05-27 | Sterling Drug Inc. | Aminomethanobenzazocines and nitromethanobenzazocines |
| CN111978252A (zh) * | 2019-05-21 | 2020-11-24 | 复旦大学 | 手性苯并吗吩烷类衍生物及其制备方法和在药学上的应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3639407A (en) * | 1965-05-05 | 1972-02-01 | Geigy Chem Corp | Novel 1 2 3 4 5 6-hexahydro-6-phenyl-2 6-methano-3-benzazocines |
| US3833595A (en) * | 1968-12-26 | 1974-09-03 | Sumitomo Chemical Co | 2-aroylalkyl benzomorphans |
| US3700734A (en) * | 1969-01-23 | 1972-10-24 | Merck & Co Inc | 2{40 -hydroxy-2,3,5-trimethyl-6,7-benzomorphan |
| US3793332A (en) * | 1972-05-22 | 1974-02-19 | Sumitomo Chemical Co | 2-cyano alkylbenzomorphan derivatives and salts thereof |
-
1973
- 1973-03-31 JP JP48037333A patent/JPS5817190B2/ja not_active Expired
-
1974
- 1974-03-27 CS CS7400002207A patent/CS183732B2/cs unknown
- 1974-03-28 DE DE2415124A patent/DE2415124A1/de not_active Ceased
- 1974-03-29 BE BE142683A patent/BE813096A/xx not_active IP Right Cessation
- 1974-03-29 SE SE7404277A patent/SE413025B/xx unknown
- 1974-03-29 AU AU67352/74A patent/AU475932B2/en not_active Expired
- 1974-03-29 HU HUSU854A patent/HU169133B/hu unknown
- 1974-03-29 SU SU742013211A patent/SU591141A3/ru active
- 1974-03-29 CH CH443174A patent/CH594628A5/xx not_active IP Right Cessation
- 1974-03-29 AT AT259274A patent/AT335630B/de not_active IP Right Cessation
- 1974-03-29 NO NO741126A patent/NO142713C/no unknown
- 1974-03-29 CA CA196,327A patent/CA1040629A/en not_active Expired
- 1974-03-29 ES ES424787A patent/ES424787A1/es not_active Expired
- 1974-03-29 US US05/456,268 patent/US3961066A/en not_active Expired - Lifetime
- 1974-03-29 ZA ZA00742013A patent/ZA742013B/xx unknown
- 1974-03-29 FR FR7411409A patent/FR2223043B1/fr not_active Expired
- 1974-03-29 FI FI972/74A patent/FI56835C/fi active
- 1974-04-01 NL NL7404411A patent/NL7404411A/xx unknown
- 1974-04-01 GB GB1432074A patent/GB1460053A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE413025B (sv) | 1980-03-31 |
| US3961066A (en) | 1976-06-01 |
| JPS5817190B2 (ja) | 1983-04-05 |
| ES424787A1 (es) | 1976-11-16 |
| CS183732B2 (en) | 1978-07-31 |
| FR2223043A1 (cs) | 1974-10-25 |
| AT335630B (de) | 1977-03-25 |
| DE2415124A1 (de) | 1974-10-10 |
| AU6735274A (en) | 1975-10-09 |
| FI56835B (fi) | 1979-12-31 |
| AU475932B2 (en) | 1976-09-09 |
| ZA742013B (en) | 1975-03-26 |
| NL7404411A (cs) | 1974-10-02 |
| NO142713C (no) | 1980-10-01 |
| SU591141A3 (ru) | 1978-01-30 |
| CH594628A5 (cs) | 1978-01-13 |
| GB1460053A (en) | 1976-12-31 |
| BE813096A (fr) | 1974-09-30 |
| ATA259274A (de) | 1976-07-15 |
| NO142713B (no) | 1980-06-23 |
| FR2223043B1 (cs) | 1977-07-01 |
| NO741126L (no) | 1974-10-01 |
| CA1040629A (en) | 1978-10-17 |
| JPS49124069A (cs) | 1974-11-27 |
| HU169133B (cs) | 1976-09-28 |
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