DE2208893A1 - Tricyclische alpha-oxy-carbonsaeurederivate und verfahren zur herstellung derselben - Google Patents
Tricyclische alpha-oxy-carbonsaeurederivate und verfahren zur herstellung derselbenInfo
- Publication number
- DE2208893A1 DE2208893A1 DE2208893A DE2208893A DE2208893A1 DE 2208893 A1 DE2208893 A1 DE 2208893A1 DE 2208893 A DE2208893 A DE 2208893A DE 2208893 A DE2208893 A DE 2208893A DE 2208893 A1 DE2208893 A1 DE 2208893A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- group
- compounds
- oxy
- substances
- 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 7
- 238000004519 manufacturing process Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- -1 ilalides Chemical class 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 5
- IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- SAQGGUMGWGCEHW-UHFFFAOYSA-N 2-hydroxy-6h-benzo[c][1]benzoxepin-11-one Chemical compound O1CC2=CC=CC=C2C(=O)C2=CC(O)=CC=C21 SAQGGUMGWGCEHW-UHFFFAOYSA-N 0.000 description 2
- YHAFLKDEDJWTNB-UHFFFAOYSA-N 4-hydroxy-6h-benzo[c][1]benzoxepin-11-one Chemical compound O1CC2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2 YHAFLKDEDJWTNB-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- OOOYVSSZZRPNFM-UHFFFAOYSA-N 2-[(2-methoxyphenoxy)methyl]benzoic acid Chemical compound COC1=CC=CC=C1OCC1=CC=CC=C1C(O)=O OOOYVSSZZRPNFM-UHFFFAOYSA-N 0.000 description 1
- YBARNBUFPMPLHH-UHFFFAOYSA-N 2-bromo-2-methylpentanoic acid Chemical compound CCCC(C)(Br)C(O)=O YBARNBUFPMPLHH-UHFFFAOYSA-N 0.000 description 1
- MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 description 1
- VJVNHFLRYLAHAU-UHFFFAOYSA-N 2-hydroxy-5,6-dihydrodibenzo[3,1-[7]annulen-11-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC(O)=CC=C21 VJVNHFLRYLAHAU-UHFFFAOYSA-N 0.000 description 1
- FPIWJQQRYHEICX-UHFFFAOYSA-N 6,11-dihydrobenzo[c][1]benzoxepine Chemical compound C1OC2=CC=CC=C2CC2=CC=CC=C12 FPIWJQQRYHEICX-UHFFFAOYSA-N 0.000 description 1
- YUSHFLBKQQILNV-UHFFFAOYSA-N 6h-benzo[c][1]benzoxepin-11-one Chemical compound C1OC2=CC=CC=C2C(=O)C2=CC=CC=C21 YUSHFLBKQQILNV-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000012067 demethylated product Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000020130 leben Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D313/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D313/12—[b,e]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2208893A DE2208893A1 (de) | 1972-02-25 | 1972-02-25 | Tricyclische alpha-oxy-carbonsaeurederivate und verfahren zur herstellung derselben |
| SU1878329A SU470956A3 (ru) | 1972-02-25 | 1973-02-01 | Способ получени трициклических производных -оксикарбоновых кислот |
| DD168927A DD105203A5 (en:Method) | 1972-02-25 | 1973-02-19 | |
| AR246667A AR194412A1 (es) | 1972-02-25 | 1973-02-19 | Un procedimiento para la preparacion de derivados de acido alpha-oxi-carboxilico tricilicos |
| NL7302352A NL7302352A (en:Method) | 1972-02-25 | 1973-02-20 | |
| GB824773A GB1361164A (en) | 1972-02-25 | 1973-02-20 | Tricyclic alpha-hydroxycarboxylic acid derivatives |
| AU52389/73A AU5238973A (en) | 1972-02-25 | 1973-02-20 | New tricyclic hydroxy-carboxylic acid derivatives |
| FR7306065A FR2181753A1 (en:Method) | 1972-02-25 | 1973-02-21 | |
| ZA731247A ZA731247B (en) | 1972-02-25 | 1973-02-22 | New tricyclic alpha-hydroxycarboxylic acid derivatives |
| HUBO1416A HU164384B (en:Method) | 1972-02-25 | 1973-02-23 | |
| JP48023057A JPS4892357A (en:Method) | 1972-02-25 | 1973-02-26 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2208893A DE2208893A1 (de) | 1972-02-25 | 1972-02-25 | Tricyclische alpha-oxy-carbonsaeurederivate und verfahren zur herstellung derselben |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2208893A1 true DE2208893A1 (de) | 1973-08-30 |
Family
ID=5837044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2208893A Pending DE2208893A1 (de) | 1972-02-25 | 1972-02-25 | Tricyclische alpha-oxy-carbonsaeurederivate und verfahren zur herstellung derselben |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS4892357A (en:Method) |
| AR (1) | AR194412A1 (en:Method) |
| AU (1) | AU5238973A (en:Method) |
| DD (1) | DD105203A5 (en:Method) |
| DE (1) | DE2208893A1 (en:Method) |
| FR (1) | FR2181753A1 (en:Method) |
| GB (1) | GB1361164A (en:Method) |
| HU (1) | HU164384B (en:Method) |
| NL (1) | NL7302352A (en:Method) |
| SU (1) | SU470956A3 (en:Method) |
| ZA (1) | ZA731247B (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6512123B2 (en) | 2001-04-23 | 2003-01-28 | Hoffmann-La Roche Inc. | Tricyclic alkylhydroxamate derivatives |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3976686A (en) * | 1972-10-13 | 1976-08-24 | Merck & Co., Inc. | [1-Oxo-2,3-hydrocarbylene-5-indanyloxy(or thio)]alkanoic acids |
| CN1110875A (zh) * | 1993-06-18 | 1995-10-25 | 大塚制药株式会社 | 芴酮衍生物，其制备方法及中枢或外周神经退化修复与保护剂 |
| FR2880887B1 (fr) * | 2005-01-14 | 2009-01-30 | Merck Sante Soc Par Actions Si | Derives d'hydroxyphenols, procedes pour leur preparation, compositions pharmaceutiques les contenant et applications en therapeutique |
-
1972
- 1972-02-25 DE DE2208893A patent/DE2208893A1/de active Pending
-
1973
- 1973-02-01 SU SU1878329A patent/SU470956A3/ru active
- 1973-02-19 AR AR246667A patent/AR194412A1/es active
- 1973-02-19 DD DD168927A patent/DD105203A5/xx unknown
- 1973-02-20 GB GB824773A patent/GB1361164A/en not_active Expired
- 1973-02-20 AU AU52389/73A patent/AU5238973A/en not_active Expired
- 1973-02-20 NL NL7302352A patent/NL7302352A/xx unknown
- 1973-02-21 FR FR7306065A patent/FR2181753A1/fr not_active Withdrawn
- 1973-02-22 ZA ZA731247A patent/ZA731247B/xx unknown
- 1973-02-23 HU HUBO1416A patent/HU164384B/hu unknown
- 1973-02-26 JP JP48023057A patent/JPS4892357A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6512123B2 (en) | 2001-04-23 | 2003-01-28 | Hoffmann-La Roche Inc. | Tricyclic alkylhydroxamate derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| AR194412A1 (es) | 1973-07-13 |
| HU164384B (en:Method) | 1974-02-28 |
| GB1361164A (en) | 1974-07-24 |
| NL7302352A (en:Method) | 1973-08-28 |
| ZA731247B (en) | 1973-12-19 |
| DD105203A5 (en:Method) | 1974-04-12 |
| JPS4892357A (en:Method) | 1973-11-30 |
| AU5238973A (en) | 1974-08-22 |
| FR2181753A1 (en:Method) | 1973-12-07 |
| SU470956A3 (ru) | 1975-05-15 |
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