DE2760419C2 - - Google Patents
Info
- Publication number
- DE2760419C2 DE2760419C2 DE19772760419 DE2760419A DE2760419C2 DE 2760419 C2 DE2760419 C2 DE 2760419C2 DE 19772760419 DE19772760419 DE 19772760419 DE 2760419 A DE2760419 A DE 2760419A DE 2760419 C2 DE2760419 C2 DE 2760419C2
- Authority
- DE
- Germany
- Prior art keywords
- morpholine
- mixture
- indenyloxymethyl
- indanyloxymethyl
- added
- 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.)
- Expired
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- MADRVGBADLFHMO-UHFFFAOYSA-N Indeloxazine Chemical compound C=1C=CC=2C=CCC=2C=1OCC1CNCCO1 MADRVGBADLFHMO-UHFFFAOYSA-N 0.000 claims description 5
- LKSJUXIZTGZHNQ-UHFFFAOYSA-N 4-(morpholin-2-ylmethoxy)-2,3-dihydro-1h-inden-1-ol Chemical compound OC1CCC2=C1C=CC=C2OCC1CNCCO1 LKSJUXIZTGZHNQ-UHFFFAOYSA-N 0.000 claims description 4
- CHJSFTHOKCJTNB-UHFFFAOYSA-N 4-(morpholin-2-ylmethoxy)-2,3-dihydroinden-1-one Chemical compound O=C1CCC2=C1C=CC=C2OCC1CNCCO1 CHJSFTHOKCJTNB-UHFFFAOYSA-N 0.000 claims description 3
- AYWVCFPWJCQEEH-UHFFFAOYSA-N 4-[(4-tritylmorpholin-2-yl)methoxy]-2,3-dihydro-1h-inden-1-ol Chemical compound OC1CCC2=C1C=CC=C2OCC(OCC1)CN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 AYWVCFPWJCQEEH-UHFFFAOYSA-N 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- KEBHLNDPKPIPLI-UHFFFAOYSA-N hydron;2-(3h-inden-4-yloxymethyl)morpholine;chloride Chemical compound Cl.C=1C=CC=2C=CCC=2C=1OCC1CNCCO1 KEBHLNDPKPIPLI-UHFFFAOYSA-N 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- -1 7-indenyloxymethyl Chemical group 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- YWPHCCPCQOJSGZ-UHFFFAOYSA-N 2-[(2-ethoxyphenoxy)methyl]morpholine Chemical compound CCOC1=CC=CC=C1OCC1OCCNC1 YWPHCCPCQOJSGZ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- WSYUEVRAMDSJKL-UHFFFAOYSA-N ethanolamine-o-sulfate Chemical compound NCCOS(O)(=O)=O WSYUEVRAMDSJKL-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 229960001255 viloxazine Drugs 0.000 description 2
- YWPHCCPCQOJSGZ-LLVKDONJSA-N (2r)-2-[(2-ethoxyphenoxy)methyl]morpholine Chemical compound CCOC1=CC=CC=C1OC[C@@H]1OCCNC1 YWPHCCPCQOJSGZ-LLVKDONJSA-N 0.000 description 1
- NWINIMXDTPZGDL-UHFFFAOYSA-N 2-(1h-inden-4-yloxymethyl)morpholine Chemical compound C=1C=CC=2CC=CC=2C=1OCC1CNCCO1 NWINIMXDTPZGDL-UHFFFAOYSA-N 0.000 description 1
- UPRMHYOLHOOBDW-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-2,3-dihydro-1h-inden-1-ol Chemical compound OC1CCC2=C1C=CC=C2OCC1CO1 UPRMHYOLHOOBDW-UHFFFAOYSA-N 0.000 description 1
- IBQHRAIYQCJZLR-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-2,3-dihydroinden-1-one Chemical compound O=C1CCC2=C1C=CC=C2OCC1CO1 IBQHRAIYQCJZLR-UHFFFAOYSA-N 0.000 description 1
- GPPMCRWIIPGDNI-UHFFFAOYSA-N C(C=C/C(=O)O)(=O)O.C1C=CC2=C(C=CC=C12)OCC1CNCCO1 Chemical compound C(C=C/C(=O)O)(=O)O.C1C=CC2=C(C=CC=C12)OCC1CNCCO1 GPPMCRWIIPGDNI-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3545076A JPS6025430B2 (ja) | 1976-03-31 | 1976-03-31 | 新規なモルホリン誘導体の製造法 |
| JP12896276A JPS6039671B2 (ja) | 1976-10-27 | 1976-10-27 | ２−（７−インデニルオキシメチル）モルホリンの酸付加塩の製法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2760419C2 true DE2760419C2 (enrdf_load_stackoverflow) | 1989-09-14 |
Family
ID=26374439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772760419 Expired DE2760419C2 (enrdf_load_stackoverflow) | 1976-03-31 | 1977-02-23 |
Country Status (4)
| Country | Link |
|---|---|
| CA (1) | CA1086732A (enrdf_load_stackoverflow) |
| DE (1) | DE2760419C2 (enrdf_load_stackoverflow) |
| DK (1) | DK145463C (enrdf_load_stackoverflow) |
| SE (1) | SE434052B (enrdf_load_stackoverflow) |
-
1977
- 1977-02-04 DK DK48977A patent/DK145463C/da not_active IP Right Cessation
- 1977-02-07 CA CA271,200A patent/CA1086732A/en not_active Expired
- 1977-02-23 DE DE19772760419 patent/DE2760419C2/de not_active Expired
- 1977-02-24 SE SE7702044A patent/SE434052B/xx not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| In Betracht gezogene ältere Anmeldung: DE-OS 26 01 703 * |
Also Published As
| Publication number | Publication date |
|---|---|
| SE7702044L (sv) | 1977-10-01 |
| DK48977A (da) | 1977-10-01 |
| DK145463B (da) | 1982-11-22 |
| DK145463C (da) | 1983-04-25 |
| SE434052B (sv) | 1984-07-02 |
| CA1086732A (en) | 1980-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| Q172 | Divided out of (supplement): |
Ref document number: 2707678 Ref country code: DE |
|
| 8181 | Inventor (new situation) |
Free format text: TAKAHASHI, KOZO MURAKAMI, MASUO, TOKIO/TOKYO, JP KOJIMA, TADAO, SAITAMA, JP NIIGATA, KUNIHIRO, AGEO, SAITAMA, JP FUJIKURA, TAKASHI, HACHIOJI, TOKIO/TOKYO, JP KAGAMA, SOICHI, KAWAGUCHI, SAITAMA, JP TACHIKAWA, SHIRO, OMIYO, SAITAMA, JP NOZAKI, YOSHIHISA, TOKIO/TOKYO, JP USUDA, SHINJI, MATSUDO, CHIBA, JP HARADA, MASATOMI, OMIYO, SAITAMA, JP |
|
| AC | Divided out of |
Ref country code: DE Ref document number: 2707678 Format of ref document f/p: P |
|
| AC | Divided out of |
Ref country code: DE Ref document number: 2707678 Format of ref document f/p: P |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |