DE2263093A1 - 7-methoxy-2,3-dihydrobenzofuranderivate und verfahren zu ihrer herstellung - Google Patents
7-methoxy-2,3-dihydrobenzofuranderivate und verfahren zu ihrer herstellungInfo
- Publication number
- DE2263093A1 DE2263093A1 DE2263093A DE2263093A DE2263093A1 DE 2263093 A1 DE2263093 A1 DE 2263093A1 DE 2263093 A DE2263093 A DE 2263093A DE 2263093 A DE2263093 A DE 2263093A DE 2263093 A1 DE2263093 A1 DE 2263093A1
- Authority
- DE
- Germany
- Prior art keywords
- methoxy
- dihydrobenzofuran
- pharmaceutically acceptable
- acid addition
- addition salts
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 8
- LQJRWEBUMYCBBV-UHFFFAOYSA-N 7-methoxy-2,3-dihydro-1-benzofuran Chemical class COC1=CC=CC2=C1OCC2 LQJRWEBUMYCBBV-UHFFFAOYSA-N 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- -1 β-phenylethyl Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
- JKKHSDXTQKFASE-UHFFFAOYSA-N (7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methanamine Chemical compound COC1=CC=CC2=C1OC(CN)C2 JKKHSDXTQKFASE-UHFFFAOYSA-N 0.000 claims 1
- QBEUAPPKMWWWIU-UHFFFAOYSA-N C(C=CC1=CC=CC=C1)C1(OC2=C(C1)C=CC=C2OC)CN Chemical compound C(C=CC1=CC=CC=C1)C1(OC2=C(C1)C=CC=C2OC)CN QBEUAPPKMWWWIU-UHFFFAOYSA-N 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 11
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- 230000000202 analgesic effect Effects 0.000 description 8
- 229940126062 Compound A Drugs 0.000 description 7
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- 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 6
- 229960005301 pentazocine Drugs 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- GRQYFFGWBBLJNV-UHFFFAOYSA-N 2-(bromomethyl)-7-methoxy-2,3-dihydro-1-benzofuran Chemical compound COC1=CC=CC2=C1OC(CBr)C2 GRQYFFGWBBLJNV-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 235000011087 fumaric acid Nutrition 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- JWYXZJIPWLIKSZ-UHFFFAOYSA-N 3'-benzylspiro[1,3-dioxolane-2,8'-3-azabicyclo[3.2.1]octane] Chemical compound C=1C=CC=CC=1CN(C1)CC2CCC1C21OCCO1 JWYXZJIPWLIKSZ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- RDAFNSMYPSHCBK-QPJJXVBHSA-N (e)-3-phenylprop-2-en-1-amine Chemical compound NC\C=C\C1=CC=CC=C1 RDAFNSMYPSHCBK-QPJJXVBHSA-N 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- LYUQWQRTDLVQGA-UHFFFAOYSA-N 3-phenylpropylamine Chemical compound NCCCC1=CC=CC=C1 LYUQWQRTDLVQGA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000005569 butenylene group Chemical group 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 108700039855 mouse a Proteins 0.000 description 1
- ZDWGYTYXGMPQIU-UHFFFAOYSA-N n-[(7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methyl]-3-phenylpropan-1-amine Chemical compound O1C=2C(OC)=CC=CC=2CC1CNCCCC1=CC=CC=C1 ZDWGYTYXGMPQIU-UHFFFAOYSA-N 0.000 description 1
- 125000003395 phenylethylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (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)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1846372A CH567011A5 (enrdf_load_stackoverflow) | 1972-12-19 | 1972-12-19 | |
| GB5899272A GB1394756A (en) | 1972-12-19 | 1972-12-21 | Pharmaceutically active benzofuran derivatives |
| DE2263093A DE2263093A1 (de) | 1972-12-19 | 1972-12-22 | 7-methoxy-2,3-dihydrobenzofuranderivate und verfahren zu ihrer herstellung |
| FR7246180A FR2211221B1 (enrdf_load_stackoverflow) | 1972-12-19 | 1972-12-26 |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1846372A CH567011A5 (enrdf_load_stackoverflow) | 1972-12-19 | 1972-12-19 | |
| GB5899272A GB1394756A (en) | 1972-12-19 | 1972-12-21 | Pharmaceutically active benzofuran derivatives |
| DE2263093A DE2263093A1 (de) | 1972-12-19 | 1972-12-22 | 7-methoxy-2,3-dihydrobenzofuranderivate und verfahren zu ihrer herstellung |
| FR7246180A FR2211221B1 (enrdf_load_stackoverflow) | 1972-12-19 | 1972-12-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2263093A1 true DE2263093A1 (de) | 1974-07-04 |
Family
ID=27429683
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2263093A Pending DE2263093A1 (de) | 1972-12-19 | 1972-12-22 | 7-methoxy-2,3-dihydrobenzofuranderivate und verfahren zu ihrer herstellung |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH567011A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2263093A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2211221B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1394756A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2905583A1 (de) * | 1978-02-20 | 1979-08-30 | Europ Propulsion | Vorrichtung zur kompensation der verstaerkung einer schaltungsanordnung mit einer strom-gegenkopplungsschleife |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4563476A (en) * | 1983-11-21 | 1986-01-07 | Merck & Co., Inc. | Substituted 5-hydroxy-2,3-dihydrobenzofurans and analogs thereof useful as anti-inflammatory agents |
| SE9902267D0 (sv) * | 1999-06-16 | 1999-06-16 | Astra Ab | New compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1344997A (fr) * | 1962-08-08 | 1963-12-06 | Ciba Geigy | Procédé de préparation de benzofurannes, entre autres du 2-(2-cyclopentyléthyl)-aminométhyl-7-méthoxy-2, 3-dihydro-benzofuranne |
-
1972
- 1972-12-19 CH CH1846372A patent/CH567011A5/de not_active IP Right Cessation
- 1972-12-21 GB GB5899272A patent/GB1394756A/en not_active Expired
- 1972-12-22 DE DE2263093A patent/DE2263093A1/de active Pending
- 1972-12-26 FR FR7246180A patent/FR2211221B1/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2905583A1 (de) * | 1978-02-20 | 1979-08-30 | Europ Propulsion | Vorrichtung zur kompensation der verstaerkung einer schaltungsanordnung mit einer strom-gegenkopplungsschleife |
Also Published As
| Publication number | Publication date |
|---|---|
| CH567011A5 (enrdf_load_stackoverflow) | 1975-09-30 |
| GB1394756A (en) | 1975-05-21 |
| FR2211221B1 (enrdf_load_stackoverflow) | 1976-08-20 |
| FR2211221A1 (enrdf_load_stackoverflow) | 1974-07-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |