DE2318575A1 - Neue oxazolidinone - Google Patents
Neue oxazolidinoneInfo
- Publication number
- DE2318575A1 DE2318575A1 DE19732318575 DE2318575A DE2318575A1 DE 2318575 A1 DE2318575 A1 DE 2318575A1 DE 19732318575 DE19732318575 DE 19732318575 DE 2318575 A DE2318575 A DE 2318575A DE 2318575 A1 DE2318575 A1 DE 2318575A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- compounds
- oxazolidinone
- preparation
- converts
- 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
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 33
- -1 alkyl radicals Chemical class 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000001414 amino alcohols Chemical class 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 1
- 230000000049 anti-anxiety effect Effects 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 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 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000037023 motor activity Effects 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000000949 anxiolytic effect Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- JBGSWIBJAGBGOP-UHFFFAOYSA-N Dehydronuciferine Natural products C1=CC=C2C3=C(OC)C(OC)=CC(CCN4C)=C3C4=CC2=C1 JBGSWIBJAGBGOP-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- QYRFJLLXPINATB-UHFFFAOYSA-N hydron;2,4,5,6-tetrafluorobenzene-1,3-diamine;dichloride Chemical compound Cl.Cl.NC1=C(F)C(N)=C(F)C(F)=C1F QYRFJLLXPINATB-UHFFFAOYSA-N 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 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
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- NFXCUPVBISCOSF-UHFFFAOYSA-N propan-2-ol;dihydrochloride Chemical compound Cl.Cl.CC(C)O NFXCUPVBISCOSF-UHFFFAOYSA-N 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7212909A FR2179582B1 (enrdf_load_stackoverflow) | 1972-04-13 | 1972-04-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2318575A1 true DE2318575A1 (de) | 1973-10-25 |
Family
ID=9096785
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732318575 Pending DE2318575A1 (de) | 1972-04-13 | 1973-04-12 | Neue oxazolidinone |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS4913166A (enrdf_load_stackoverflow) |
| BE (1) | BE797969A (enrdf_load_stackoverflow) |
| DE (1) | DE2318575A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2179582B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1398687A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2538424A1 (de) * | 1975-08-29 | 1977-03-03 | Nordmark Werke Gmbh | Neue oxazolidinone, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| DE3519261A1 (de) * | 1984-09-28 | 1986-04-10 | Nippon Chemiphar Co. Ltd., Tokio/Tokyo | 1,3-oxazolidin-2-on derivat und verfahren zu seiner herstellung |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS544738Y2 (enrdf_load_stackoverflow) * | 1974-12-02 | 1979-02-28 | ||
| JPH0620695Y2 (ja) * | 1987-06-04 | 1994-06-01 | 日産自動車株式会社 | 自動車用成形天井の取付構造 |
| EP0636623B1 (en) * | 1990-06-07 | 2001-08-16 | AstraZeneca AB | Indole derivatives as 5-HT1- like agonists |
-
1972
- 1972-04-13 FR FR7212909A patent/FR2179582B1/fr not_active Expired
-
1973
- 1973-04-09 BE BE129819A patent/BE797969A/xx unknown
- 1973-04-12 DE DE19732318575 patent/DE2318575A1/de active Pending
- 1973-04-13 GB GB1798673A patent/GB1398687A/en not_active Expired
- 1973-04-13 JP JP4206273A patent/JPS4913166A/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2538424A1 (de) * | 1975-08-29 | 1977-03-03 | Nordmark Werke Gmbh | Neue oxazolidinone, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| DE3519261A1 (de) * | 1984-09-28 | 1986-04-10 | Nippon Chemiphar Co. Ltd., Tokio/Tokyo | 1,3-oxazolidin-2-on derivat und verfahren zu seiner herstellung |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2179582A1 (enrdf_load_stackoverflow) | 1973-11-23 |
| JPS4913166A (enrdf_load_stackoverflow) | 1974-02-05 |
| BE797969A (fr) | 1973-10-09 |
| FR2179582B1 (enrdf_load_stackoverflow) | 1975-10-10 |
| GB1398687A (en) | 1975-06-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3046719C2 (de) | 1,1,2-Triphenyl-but-1-en-Derivate, Verfahren zu ihrer Herstellung und Arzneimittel | |
| AT363096B (de) | Verfahren zur herstellung von neuen phthalazinderivaten und deren salzen | |
| DE3026201C2 (enrdf_load_stackoverflow) | ||
| DE2434911C2 (de) | Phenyläthylamin-Derivate und pharmazeutische Zusammensetzungen | |
| DE3707651A1 (de) | Bis-naphthalimide, ihre herstellung und verwendung | |
| DE1670048A1 (de) | Verfahren zur Herstellung von neuen Norscopolamin-derivaten und deren Quartaersalzen | |
| DE1593579B1 (de) | Hydroxy-cyclohexylamine,deren physiologisch vertraeglichen Saeureadditionssalze und Verfahren zu ihrer Herstellung | |
| CH643549A5 (de) | N-(trimethoxybenzyl)-n'-phenylpiperazine. | |
| DE1518452C3 (de) | 4 substituierte 2 Benzhydryl 2 butanol Derivate und Verfahren zu ihrer Herstellung | |
| DE2833505A1 (de) | Tetrahydro-isochinolin-derivate, verfahren zu deren herstellung und mittel enthaltend die derivate | |
| DE2318575A1 (de) | Neue oxazolidinone | |
| DE2729165C2 (de) | Phenäthylaminderivate und deren Salze, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen | |
| AT345781B (de) | Verfahren zur herstellung von neuen 3- aminomethyl-2-phenylbicyclo (2,2,2) octanen und -octenen sowie deren saeureadditionssalzen | |
| EP0107208B1 (de) | Neue 1,1,2-Triphenyl-but-1-en-Derivate, sowie Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel | |
| DE1177633B (de) | Verfahren zur Herstellung aminoalkylierter 9,10-Dihydroanthracene | |
| DE3102597C2 (enrdf_load_stackoverflow) | ||
| DE2846880A1 (de) | Substituierte chinolizidin- und indolizidinmethanolderivate, verfahren zur herstellung derselben und arzneimittel, welche diese enthalten | |
| DE2142792A1 (de) | Heterocyclische Verbindungen | |
| DE2239606A1 (de) | 4-phenoxy 3-hydroxy-butyramidine und derivate | |
| DE2822473A1 (de) | Alkanolaminderivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zusammensetzungen | |
| AT226723B (de) | Verfahren zur Umwandlung von Thiaxanthenen | |
| AT313889B (de) | Verfahren zur Herstellung von neuen 2-(Furyl-methyl)-6,7-benzomorphanderivaten und deren Säureadditionssalzen | |
| DE2638849A1 (de) | Aminosaeureester, verfahren zu ihrer herstellung und sie enthaltende arzneimittel | |
| AT275497B (de) | Verfahren zur Herstellung von neuen 1-Dialkylaminoadamantanen und ihren Salzen | |
| AT257058B (de) | Verfahren zur Herstellung des neuen bis-Pyridylmethyl-disulfids |