FR2471378A1 - Derives de 2-phenyl-morpholine, leur procede de preparation et leur application en therapeutique - Google Patents
Derives de 2-phenyl-morpholine, leur procede de preparation et leur application en therapeutique Download PDFInfo
- Publication number
- FR2471378A1 FR2471378A1 FR7930768A FR7930768A FR2471378A1 FR 2471378 A1 FR2471378 A1 FR 2471378A1 FR 7930768 A FR7930768 A FR 7930768A FR 7930768 A FR7930768 A FR 7930768A FR 2471378 A1 FR2471378 A1 FR 2471378A1
- Authority
- FR
- France
- Prior art keywords
- phenyl
- sep
- crl
- addition salts
- morpholine
- 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.)
- Granted
Links
- -1 hydroxyalkyl phenyl ethanol Chemical compound 0.000 title claims description 5
- 239000000935 antidepressant agent Substances 0.000 title abstract description 6
- 229940005513 antidepressants Drugs 0.000 title abstract description 5
- 230000001430 anti-depressive effect Effects 0.000 title description 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-Phenylethanol Natural products OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 title 1
- FHQRDEDZJIFJAL-UHFFFAOYSA-N 4-phenylmorpholine Chemical compound C1COCCN1C1=CC=CC=C1 FHQRDEDZJIFJAL-UHFFFAOYSA-N 0.000 title 1
- 230000005792 cardiovascular activity Effects 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- ZLNGFYDJXZZFJP-UHFFFAOYSA-N 2-phenylmorpholine Chemical compound C1NCCOC1C1=CC=CC=C1 ZLNGFYDJXZZFJP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 5
- 231100000252 nontoxic Toxicity 0.000 claims description 4
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- YAOKPRXVGSXSND-UHFFFAOYSA-N 4-tert-butyl-2-phenylmorpholine Chemical compound C1N(C(C)(C)C)CCOC1C1=CC=CC=C1 YAOKPRXVGSXSND-UHFFFAOYSA-N 0.000 claims description 2
- KJUOROGOOZJYAI-UHFFFAOYSA-N 5,5-dimethyl-2-phenylmorpholine Chemical compound C1NC(C)(C)COC1C1=CC=CC=C1 KJUOROGOOZJYAI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- CHHFZVOTWWUPDQ-UHFFFAOYSA-N 2-phenyl-4-propan-2-ylmorpholine Chemical compound C1N(C(C)C)CCOC1C1=CC=CC=C1 CHHFZVOTWWUPDQ-UHFFFAOYSA-N 0.000 claims 1
- LQHGEOIBMBXJGV-UHFFFAOYSA-N 5-methyl-2-phenylmorpholine Chemical compound C1NC(C)COC1C1=CC=CC=C1 LQHGEOIBMBXJGV-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 8
- 239000007858 starting material Substances 0.000 abstract description 2
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- BGRJTUBHPOOWDU-NSHDSACASA-N (S)-(-)-sulpiride Chemical compound CCN1CCC[C@H]1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-NSHDSACASA-N 0.000 description 1
- BFAQNLRAFSBFGU-UHFFFAOYSA-N 1-amino-1-phenylethanol Chemical compound CC(N)(O)C1=CC=CC=C1 BFAQNLRAFSBFGU-UHFFFAOYSA-N 0.000 description 1
- RILLZYSZSDGYGV-UHFFFAOYSA-N 2-(propan-2-ylamino)ethanol Chemical compound CC(C)NCCO RILLZYSZSDGYGV-UHFFFAOYSA-N 0.000 description 1
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- OFQCQIGMURIECL-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-2',6'-dimethylspiro[isoquinoline-4,4'-oxane]-1,3-dione;phosphoric acid Chemical compound OP(O)(O)=O.O=C1N(CCN(CC)CC)C(=O)C2=CC=CC=C2C21CC(C)OC(C)C2 OFQCQIGMURIECL-UHFFFAOYSA-N 0.000 description 1
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- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
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- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7930768A FR2471378A1 (fr) | 1979-12-14 | 1979-12-14 | Derives de 2-phenyl-morpholine, leur procede de preparation et leur application en therapeutique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7930768A FR2471378A1 (fr) | 1979-12-14 | 1979-12-14 | Derives de 2-phenyl-morpholine, leur procede de preparation et leur application en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2471378A1 true FR2471378A1 (fr) | 1981-06-19 |
| FR2471378B1 FR2471378B1 (enExample) | 1983-03-25 |
Family
ID=9232811
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7930768A Granted FR2471378A1 (fr) | 1979-12-14 | 1979-12-14 | Derives de 2-phenyl-morpholine, leur procede de preparation et leur application en therapeutique |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2471378A1 (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0080940A3 (en) * | 1981-12-01 | 1983-07-06 | Laboratoire L. Lafon Societe Anonyme Dite: | Derivatives of 2-phenyl-morpholine and their uses as medicines |
| WO1993015052A1 (en) * | 1992-01-28 | 1993-08-05 | Smithkline Beecham Plc | Compounds as calcium channel antagonists |
| US7132551B2 (en) | 2000-09-11 | 2006-11-07 | Sepracor Inc. | Ligands for monoamine receptors and transporters, and methods of use thereof |
| US7294637B2 (en) | 2000-09-11 | 2007-11-13 | Sepracor, Inc. | Method of treating addiction or dependence using a ligand for a monamine receptor or transporter |
| JP2013526583A (ja) * | 2010-05-21 | 2013-06-24 | リサーチ・トライアングル・インスティチュート | フェニルモルホリンおよびその類似体 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2835669A (en) * | 1958-05-20 | Process for the production of substi- | ||
| US2997469A (en) * | 1961-08-22 | Preparation of substituted | ||
| FR7443M (enExample) * | 1968-03-04 | 1969-11-17 | ||
| FR2111882A1 (enExample) * | 1970-10-28 | 1972-06-09 | Gentili Ist Spa |
-
1979
- 1979-12-14 FR FR7930768A patent/FR2471378A1/fr active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2835669A (en) * | 1958-05-20 | Process for the production of substi- | ||
| US2997469A (en) * | 1961-08-22 | Preparation of substituted | ||
| FR7443M (enExample) * | 1968-03-04 | 1969-11-17 | ||
| FR2111882A1 (enExample) * | 1970-10-28 | 1972-06-09 | Gentili Ist Spa |
Non-Patent Citations (1)
| Title |
|---|
| EXBK/76 * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0080940A3 (en) * | 1981-12-01 | 1983-07-06 | Laboratoire L. Lafon Societe Anonyme Dite: | Derivatives of 2-phenyl-morpholine and their uses as medicines |
| WO1993015052A1 (en) * | 1992-01-28 | 1993-08-05 | Smithkline Beecham Plc | Compounds as calcium channel antagonists |
| US7132551B2 (en) | 2000-09-11 | 2006-11-07 | Sepracor Inc. | Ligands for monoamine receptors and transporters, and methods of use thereof |
| US7294637B2 (en) | 2000-09-11 | 2007-11-13 | Sepracor, Inc. | Method of treating addiction or dependence using a ligand for a monamine receptor or transporter |
| US7517892B2 (en) | 2000-09-11 | 2009-04-14 | Sepracor Inc. | Ligands for monoamine receptors and transporters, and methods of use thereof |
| US7816375B2 (en) | 2000-09-11 | 2010-10-19 | Sepracor Inc. | Ligands for monoamine receptors and transporters, and methods of use thereof |
| JP2013526583A (ja) * | 2010-05-21 | 2013-06-24 | リサーチ・トライアングル・インスティチュート | フェニルモルホリンおよびその類似体 |
| US20130203752A1 (en) * | 2010-05-21 | 2013-08-08 | Bruce E. Blough | Phenylmorpholines and analogues thereof |
| US9617229B2 (en) * | 2010-05-21 | 2017-04-11 | Research Triangle Institute | Phenylmorpholines and analogues thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2471378B1 (enExample) | 1983-03-25 |
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