CH513904A - Verfahren zur Herstellung von Morpholinderivaten - Google Patents
Verfahren zur Herstellung von MorpholinderivatenInfo
- Publication number
- CH513904A CH513904A CH1760370A CH1760370A CH513904A CH 513904 A CH513904 A CH 513904A CH 1760370 A CH1760370 A CH 1760370A CH 1760370 A CH1760370 A CH 1760370A CH 513904 A CH513904 A CH 513904A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- radical
- alkyl
- radicals
- maximum
- Prior art date
Links
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 title abstract description 12
- 230000000694 effects Effects 0.000 title abstract description 4
- 239000002253 acid Substances 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- -1 alkyl radicals Chemical class 0.000 claims description 62
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 150000002780 morpholines Chemical class 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000005248 alkyl aryloxy group Chemical group 0.000 claims description 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical group O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000047 product Substances 0.000 claims 4
- 239000013067 intermediate product Substances 0.000 claims 1
- 230000001519 thymoleptic effect Effects 0.000 abstract description 4
- 238000011282 treatment Methods 0.000 abstract description 4
- 206010015037 epilepsy Diseases 0.000 abstract description 2
- 150000007522 mineralic acids Chemical class 0.000 abstract description 2
- 150000007524 organic acids Chemical class 0.000 abstract description 2
- 238000011321 prophylaxis Methods 0.000 abstract description 2
- 208000020401 Depressive disease Diseases 0.000 abstract 1
- 241000124008 Mammalia Species 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- QCZSSIYNGDQFGO-UHFFFAOYSA-N 2-[(2-ethoxyphenoxy)methyl]-3-methylmorpholine Chemical compound C(C)OC1=C(OCC2C(NCCO2)C)C=CC=C1 QCZSSIYNGDQFGO-UHFFFAOYSA-N 0.000 description 2
- YWPHCCPCQOJSGZ-UHFFFAOYSA-N 2-[(2-ethoxyphenoxy)methyl]morpholine Chemical compound CCOC1=CC=CC=C1OCC1OCCNC1 YWPHCCPCQOJSGZ-UHFFFAOYSA-N 0.000 description 2
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000002964 excitative effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical class O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 1
- KBCDUOMJRACHMF-UHFFFAOYSA-N 2-(morpholin-2-ylmethoxy)phenol Chemical compound OC1=CC=CC=C1OCC1OCCNC1 KBCDUOMJRACHMF-UHFFFAOYSA-N 0.000 description 1
- AQCZCAJLZOBIBE-UHFFFAOYSA-N 2-(naphthalen-1-yloxymethyl)morpholine Chemical compound C=1C=CC2=CC=CC=C2C=1OCC1CNCCO1 AQCZCAJLZOBIBE-UHFFFAOYSA-N 0.000 description 1
- OFBLNBCFCXAZGW-UHFFFAOYSA-N 2-(phenoxymethyl)morpholine Chemical compound C1NCCOC1COC1=CC=CC=C1 OFBLNBCFCXAZGW-UHFFFAOYSA-N 0.000 description 1
- VBBMCRRQNCBJQP-UHFFFAOYSA-N 2-[(2,6-dimethoxyphenoxy)methyl]morpholine Chemical compound COC1=CC=CC(OC)=C1OCC1OCCNC1 VBBMCRRQNCBJQP-UHFFFAOYSA-N 0.000 description 1
- CHUROPRTMCQLIS-UHFFFAOYSA-N 2-[(2-methoxyphenoxy)methyl]morpholine Chemical compound COC1=CC=CC=C1OCC1OCCNC1 CHUROPRTMCQLIS-UHFFFAOYSA-N 0.000 description 1
- VUMNCOIUUGRFQR-UHFFFAOYSA-N 2-[(2-methylphenoxy)methyl]morpholine Chemical compound CC1=CC=CC=C1OCC1OCCNC1 VUMNCOIUUGRFQR-UHFFFAOYSA-N 0.000 description 1
- HETODBVDFUTLCL-UHFFFAOYSA-N 2-[(2-methylphenyl)sulfanylmethyl]morpholine Chemical compound CC1=CC=CC=C1SCC1OCCNC1 HETODBVDFUTLCL-UHFFFAOYSA-N 0.000 description 1
- CPAXVDGZFMOFIM-UHFFFAOYSA-N 2-[(2-phenoxyphenoxy)methyl]morpholine Chemical compound C1NCCOC1COC1=CC=CC=C1OC1=CC=CC=C1 CPAXVDGZFMOFIM-UHFFFAOYSA-N 0.000 description 1
- LDTYVJVIAZQLRQ-UHFFFAOYSA-N 2-[(2-propan-2-yloxyphenoxy)methyl]morpholine Chemical compound C(C)(C)OC1=C(OCC2CNCCO2)C=CC=C1 LDTYVJVIAZQLRQ-UHFFFAOYSA-N 0.000 description 1
- UXANZBNZUHNWBR-UHFFFAOYSA-N 2-[(2-propoxyphenoxy)methyl]morpholine Chemical compound CCCOC1=CC=CC=C1OCC1OCCNC1 UXANZBNZUHNWBR-UHFFFAOYSA-N 0.000 description 1
- CAIBSLGEKNOIJR-UHFFFAOYSA-N 2-[(3-methoxyphenoxy)methyl]morpholine Chemical compound COC1=CC=CC(OCC2OCCNC2)=C1 CAIBSLGEKNOIJR-UHFFFAOYSA-N 0.000 description 1
- CPIIBXDVKCDHMA-UHFFFAOYSA-N 2-[(4-methoxyphenoxy)methyl]morpholine Chemical compound C1=CC(OC)=CC=C1OCC1OCCNC1 CPIIBXDVKCDHMA-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- RYJNVYZKENJENW-UHFFFAOYSA-N 4-benzyl-2-[(2-ethoxyphenoxy)methyl]morpholine Chemical compound CCOC1=CC=CC=C1OCC1OCCN(CC=2C=CC=CC=2)C1 RYJNVYZKENJENW-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- MOGNHKOHVIIIBL-UHFFFAOYSA-N C(C)(=O)O.C(C)OC1=C(OCC2CNCCO2)C=CC=C1 Chemical compound C(C)(=O)O.C(C)OC1=C(OCC2CNCCO2)C=CC=C1 MOGNHKOHVIIIBL-UHFFFAOYSA-N 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
- 206010010904 Convulsion Diseases 0.000 description 1
- OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical class [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 150000000994 L-ascorbates Chemical class 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 230000002567 autonomic effect Effects 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 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
- 230000001914 calming effect Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 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
-
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04B—KNITTING
- D04B1/00—Weft knitting processes for the production of fabrics or articles not dependent on the use of particular machines; Fabrics or articles defined by such processes
- D04B1/22—Weft knitting processes for the production of fabrics or articles not dependent on the use of particular machines; Fabrics or articles defined by such processes specially adapted for knitting goods of particular configuration
- D04B1/24—Weft knitting processes for the production of fabrics or articles not dependent on the use of particular machines; Fabrics or articles defined by such processes specially adapted for knitting goods of particular configuration wearing apparel
- D04B1/26—Weft knitting processes for the production of fabrics or articles not dependent on the use of particular machines; Fabrics or articles defined by such processes specially adapted for knitting goods of particular configuration wearing apparel stockings
-
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04B—KNITTING
- D04B9/00—Circular knitting machines with independently-movable needles
- D04B9/42—Circular knitting machines with independently-movable needles specially adapted for producing goods of particular configuration
- D04B9/46—Circular knitting machines with independently-movable needles specially adapted for producing goods of particular configuration stockings, or portions thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Orthopedics, Nursing, And Contraception (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB57963/66A GB1138405A (en) | 1966-12-28 | 1966-12-28 | Morpholine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH513904A true CH513904A (de) | 1971-11-30 |
Family
ID=10480469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1760370A CH513904A (de) | 1966-12-28 | 1967-12-01 | Verfahren zur Herstellung von Morpholinderivaten |
Country Status (11)
| Country | Link |
|---|---|
| AT (2) | AT274826B (enExample) |
| CH (1) | CH513904A (enExample) |
| DK (1) | DK120543B (enExample) |
| ES (1) | ES348087A1 (enExample) |
| FI (1) | FI47373C (enExample) |
| IL (1) | IL29033A (enExample) |
| MY (1) | MY7200092A (enExample) |
| NO (1) | NO126021B (enExample) |
| PL (1) | PL69864B1 (enExample) |
| SE (1) | SE334157B (enExample) |
| YU (3) | YU32606B (enExample) |
-
1967
- 1967-11-20 NO NO170607A patent/NO126021B/no unknown
- 1967-11-27 DK DK592367AA patent/DK120543B/da not_active IP Right Cessation
- 1967-11-28 AT AT1072967A patent/AT274826B/de active
- 1967-11-28 AT AT10148/68A patent/AT281853B/de not_active IP Right Cessation
- 1967-11-29 IL IL29033A patent/IL29033A/en unknown
- 1967-11-30 FI FI673216A patent/FI47373C/fi active
- 1967-12-01 CH CH1760370A patent/CH513904A/de not_active IP Right Cessation
- 1967-12-09 ES ES348087A patent/ES348087A1/es not_active Expired
- 1967-12-13 SE SE17125/67A patent/SE334157B/xx unknown
- 1967-12-19 YU YU2475/67A patent/YU32606B/xx unknown
- 1967-12-27 PL PL1967124356A patent/PL69864B1/pl unknown
-
1972
- 1972-12-31 MY MY197292A patent/MY7200092A/xx unknown
-
1973
- 1973-03-05 YU YU574/73A patent/YU34794B/xx unknown
- 1973-03-05 YU YU575/73A patent/YU35130B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO126021B (enExample) | 1972-12-11 |
| FI47373B (enExample) | 1973-07-31 |
| YU57473A (en) | 1979-09-10 |
| ES348087A1 (es) | 1969-03-01 |
| SE334157B (enExample) | 1971-04-19 |
| AT274826B (de) | 1969-10-10 |
| YU32606B (en) | 1975-04-30 |
| YU35130B (en) | 1980-09-25 |
| YU247567A (en) | 1974-10-31 |
| AT281853B (de) | 1970-06-10 |
| IL29033A (en) | 1972-01-27 |
| FI47373C (fi) | 1973-11-12 |
| PL69864B1 (en) | 1973-10-31 |
| YU34794B (en) | 1980-03-15 |
| YU57573A (en) | 1980-03-15 |
| MY7200092A (en) | 1972-12-31 |
| DK120543B (da) | 1971-06-14 |
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