DE2205676A1 - 4-Aryl-4-oxazolin-2-one mit myotonischer oder myröelaxierender Wirkung und Verfahren zu deren Herstellung - Google Patents
4-Aryl-4-oxazolin-2-one mit myotonischer oder myröelaxierender Wirkung und Verfahren zu deren HerstellungInfo
- Publication number
- DE2205676A1 DE2205676A1 DE19722205676 DE2205676A DE2205676A1 DE 2205676 A1 DE2205676 A1 DE 2205676A1 DE 19722205676 DE19722205676 DE 19722205676 DE 2205676 A DE2205676 A DE 2205676A DE 2205676 A1 DE2205676 A1 DE 2205676A1
- Authority
- DE
- Germany
- Prior art keywords
- aryl
- oxazolin
- formula
- carbamate
- ones
- 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 24
- 230000003274 myotonic effect Effects 0.000 title claims description 8
- 230000000694 effects Effects 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 6
- 238000006243 chemical reaction Methods 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
- 230000001670 myorelaxant effect Effects 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 210000003169 central nervous system Anatomy 0.000 claims description 4
- 210000003205 muscle Anatomy 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 claims description 3
- 230000004936 stimulating effect Effects 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims 3
- 239000007864 aqueous solution Substances 0.000 claims 1
- 230000003416 augmentation Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
- 239000013078 crystal Substances 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- -1 2- (4'-bromophenyl) -2-oxoethyl carbamate Chemical compound 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- ADLHLYYJPWMYJC-UHFFFAOYSA-N phenacyl carbamate Chemical compound NC(=O)OCC(=O)C1=CC=CC=C1 ADLHLYYJPWMYJC-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003158 myorelaxant agent Substances 0.000 description 3
- 150000002918 oxazolines Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- JWDYCNIAQWPBHD-UHFFFAOYSA-N 1-(2-methylphenyl)glycerol Chemical compound CC1=CC=CC=C1OCC(O)CO JWDYCNIAQWPBHD-UHFFFAOYSA-N 0.000 description 2
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical compound OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 2
- UPULOMQHYQDNNT-UHFFFAOYSA-N 5h-1,3-oxazol-2-one Chemical compound O=C1OCC=N1 UPULOMQHYQDNNT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical class COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 2
- 229910001626 barium chloride Inorganic materials 0.000 description 2
- 230000001914 calming effect Effects 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001960 triggered effect Effects 0.000 description 2
- GCGBPPCSOJNFDC-UHFFFAOYSA-N 2-oxoethyl carbamate Chemical class NC(=O)OCC=O GCGBPPCSOJNFDC-UHFFFAOYSA-N 0.000 description 1
- AMHMBEIWHHGAMZ-UHFFFAOYSA-N 3-(4-chlorophenyl)-1,3-oxazol-2-one Chemical compound ClC1=CC=C(C=C1)N1C(OC=C1)=O AMHMBEIWHHGAMZ-UHFFFAOYSA-N 0.000 description 1
- XYVMOLOUBJBNBF-UHFFFAOYSA-N 3h-1,3-oxazol-2-one Chemical compound OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 description 1
- CCGBNUKHCLUUFX-UHFFFAOYSA-N 4-naphthalen-2-yl-3h-1,3-oxazol-2-one Chemical compound O1C(=O)NC(C=2C=C3C=CC=CC3=CC=2)=C1 CCGBNUKHCLUUFX-UHFFFAOYSA-N 0.000 description 1
- 150000000527 4-oxazolines Chemical class 0.000 description 1
- FXJBHVJHXKVCQM-UHFFFAOYSA-N 4-phenyl-3h-1,3-oxazol-2-one Chemical compound O1C(=O)NC(C=2C=CC=CC=2)=C1 FXJBHVJHXKVCQM-UHFFFAOYSA-N 0.000 description 1
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 230000001663 anti-spastic effect Effects 0.000 description 1
- 239000000729 antidote Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000001595 contractor effect Effects 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229960004279 formaldehyde Drugs 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229960003861 mephenesin Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229960001789 papaverine Drugs 0.000 description 1
- 229960005152 pentetrazol Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- LIXWSNVLHFNXAJ-UHFFFAOYSA-N sodium;oxidoazaniumylidynemethane Chemical compound [Na+].[O-][N+]#[C-] LIXWSNVLHFNXAJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D263/36—One oxygen atom
- C07D263/38—One oxygen atom attached in position 2
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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT6830672A IT954784B (it) | 1971-06-24 | 1972-04-27 | Dispositivo indicatore del dia framma per obiettivi particolar mente per obiettivi di ingrandi mento |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT4521071 | 1971-02-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2205676A1 true DE2205676A1 (de) | 1972-08-24 |
Family
ID=11256775
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722205676 Pending DE2205676A1 (de) | 1971-02-08 | 1972-02-09 | 4-Aryl-4-oxazolin-2-one mit myotonischer oder myröelaxierender Wirkung und Verfahren zu deren Herstellung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3879410A (enExample) |
| DE (1) | DE2205676A1 (enExample) |
| ES (1) | ES399572A1 (enExample) |
| FR (1) | FR2124468B1 (enExample) |
| GB (1) | GB1386613A (enExample) |
| SE (1) | SE370239B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0223177A1 (en) * | 1985-11-13 | 1987-05-27 | Merrell Dow Pharmaceuticals Inc. | Cardiotonic phenyl oxazolones |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2610676A1 (de) * | 1976-03-13 | 1977-09-15 | Bayer Ag | Delta hoch 4-oxazolinone-2 |
| US4698353A (en) * | 1985-11-13 | 1987-10-06 | Merrell Dow Pharmaceuticals Inc. | Cardiotonic heterocyclic oxazolones |
| HU219974B (hu) * | 1990-06-07 | 2001-10-28 | Astrazeneca Ab, | Heterociklusos csoporttal helyettesített indolszármazék, előállítása és a vegyületet hatóanyagként tartalmazó gyógyszerkészítmények |
| GB9516145D0 (en) * | 1995-08-07 | 1995-10-04 | Wellcome Found | Improved chemical synthesis |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1155958A (en) * | 1965-10-11 | 1969-06-25 | Agfa Gevaert Nv | Light-Developable Photographic Material and Recording process |
-
1972
- 1972-02-03 US US223090A patent/US3879410A/en not_active Expired - Lifetime
- 1972-02-04 FR FR7203740A patent/FR2124468B1/fr not_active Expired
- 1972-02-07 GB GB550772A patent/GB1386613A/en not_active Expired
- 1972-02-07 SE SE7201371A patent/SE370239B/xx unknown
- 1972-02-08 ES ES399572A patent/ES399572A1/es not_active Expired
- 1972-02-09 DE DE19722205676 patent/DE2205676A1/de active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0223177A1 (en) * | 1985-11-13 | 1987-05-27 | Merrell Dow Pharmaceuticals Inc. | Cardiotonic phenyl oxazolones |
| US4728661A (en) * | 1985-11-13 | 1988-03-01 | Merrell Dow Pharmaceuticals Inc. | Cardiotonic phenyl oxazolones |
Also Published As
| Publication number | Publication date |
|---|---|
| ES399572A1 (es) | 1974-11-01 |
| FR2124468A1 (enExample) | 1972-09-22 |
| SE370239B (enExample) | 1974-10-07 |
| GB1386613A (en) | 1975-03-12 |
| FR2124468B1 (enExample) | 1976-04-16 |
| US3879410A (en) | 1975-04-22 |
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