DE2110363A1 - Carbonsaeureamid- und Carbonsaeurehydrazidderivate von 4,5-Diphenyloxazol und Verfahren zu ihrer Herstellung - Google Patents
Carbonsaeureamid- und Carbonsaeurehydrazidderivate von 4,5-Diphenyloxazol und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2110363A1 DE2110363A1 DE19712110363 DE2110363A DE2110363A1 DE 2110363 A1 DE2110363 A1 DE 2110363A1 DE 19712110363 DE19712110363 DE 19712110363 DE 2110363 A DE2110363 A DE 2110363A DE 2110363 A1 DE2110363 A1 DE 2110363A1
- Authority
- DE
- Germany
- Prior art keywords
- diphenyl
- oxazolyl
- acid
- radical
- carboxylic acid
- 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 7
- ODKHOKLXMBWVOQ-UHFFFAOYSA-N 4,5-diphenyl-1,3-oxazole Chemical class O1C=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 ODKHOKLXMBWVOQ-UHFFFAOYSA-N 0.000 title claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- -1 4,5-Diphenyl-2-oxazolylacetic acid-N, N-diethylamide Chemical compound 0.000 claims description 13
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- PAFQEVXJDAMGSR-UHFFFAOYSA-N 2-(4,5-diphenyl-1,3-oxazol-2-yl)acetohydrazide Chemical compound C1(=CC=CC=C1)C=1N=C(OC1C1=CC=CC=C1)CC(=O)NN PAFQEVXJDAMGSR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
- PZOQPILRTHLFLZ-UHFFFAOYSA-N 3-(4,5-diphenyl-1,3-oxazol-2-yl)-1-pyrrolidin-1-ylpropan-1-one Chemical compound C1CCCN1C(=O)CCC(O1)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PZOQPILRTHLFLZ-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- MLIVKNLPWGHWRM-UHFFFAOYSA-N 3-(4,5-diphenyl-1,3-oxazol-2-yl)-n-methylpropanamide Chemical compound O1C(CCC(=O)NC)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 MLIVKNLPWGHWRM-UHFFFAOYSA-N 0.000 claims description 2
- 238000007098 aminolysis reaction Methods 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000003857 carboxamides Chemical class 0.000 claims description 2
- 238000006698 hydrazinolysis reaction Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- ROFVGYAMRSGUSQ-UHFFFAOYSA-N 1-(2-bromoethyl)piperazine;hydrobromide Chemical compound Br.BrCCN1CCNCC1 ROFVGYAMRSGUSQ-UHFFFAOYSA-N 0.000 claims 1
- OXOFJDTYAGNUJY-UHFFFAOYSA-N 2-(4,5-diphenyl-1,3-oxazol-2-yl)-1-pyrrolidin-1-ylethanone Chemical compound C1(=CC=CC=C1)C=1N=C(OC1C1=CC=CC=C1)CC(=O)N1CCCC1 OXOFJDTYAGNUJY-UHFFFAOYSA-N 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 239000000203 mixture Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 239000004305 biphenyl 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RRRQDMLSVFUTTC-UHFFFAOYSA-N ethyl 2-(4,5-diphenyl-1,3-oxazol-2-yl)acetate Chemical compound O1C(CC(=O)OCC)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 RRRQDMLSVFUTTC-UHFFFAOYSA-N 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- OFPXSFXSNFPTHF-UHFFFAOYSA-N oxaprozin Chemical compound O1C(CCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 OFPXSFXSNFPTHF-UHFFFAOYSA-N 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- CQHYICHMGNSGQH-UHFFFAOYSA-N 1,3-oxazole-2-carboxylic acid Chemical compound OC(=O)C1=NC=CO1 CQHYICHMGNSGQH-UHFFFAOYSA-N 0.000 description 1
- YPXDNSOFUCIWRD-UHFFFAOYSA-N 3-(4,5-diphenyl-1,3-oxazol-2-yl)-1-morpholin-4-ylpropan-1-one Chemical compound C1COCCN1C(=O)CCC(O1)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 YPXDNSOFUCIWRD-UHFFFAOYSA-N 0.000 description 1
- SAWPNVIAXSUMKQ-UHFFFAOYSA-N 3-(4,5-diphenyl-1,3-oxazol-2-yl)propanehydrazide Chemical compound C1(=CC=CC=C1)C=1N=C(OC1C1=CC=CC=C1)CCC(=O)NN SAWPNVIAXSUMKQ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- KWFADUNOPOSMIJ-UHFFFAOYSA-N ethyl 3-chloro-3-oxopropanoate Chemical compound CCOC(=O)CC(Cl)=O KWFADUNOPOSMIJ-UHFFFAOYSA-N 0.000 description 1
- WKSYCGROFUCSHR-UHFFFAOYSA-N ethyl 4,5-diphenyl-1,3-oxazole-2-carboxylate Chemical compound O1C(C(=O)OCC)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 WKSYCGROFUCSHR-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 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
-
- 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
- C07D263/32—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic 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 |
|---|---|---|---|
| IT21550/70A IT1043805B (it) | 1970-03-05 | 1970-03-05 | Ammidi e idrazidi di acidi carbos silici derivanti dal 4,5,difenilossazolo e processo per la loro preparazione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2110363A1 true DE2110363A1 (de) | 1971-09-16 |
Family
ID=11183453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712110363 Pending DE2110363A1 (de) | 1970-03-05 | 1971-03-04 | Carbonsaeureamid- und Carbonsaeurehydrazidderivate von 4,5-Diphenyloxazol und Verfahren zu ihrer Herstellung |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3869455A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS504663B1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA949580A (cg-RX-API-DMAC7.html) |
| CH (1) | CH555846A (cg-RX-API-DMAC7.html) |
| DE (1) | DE2110363A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2085675B1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1293702A (cg-RX-API-DMAC7.html) |
| IT (1) | IT1043805B (cg-RX-API-DMAC7.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5262540A (en) * | 1989-12-20 | 1993-11-16 | Bristol-Myers Squibb Company | [2(4,5-diaryl-2 oxazoyl substituted phenoxy alkanoic acid and esters |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2677355B1 (fr) * | 1991-06-06 | 1993-08-20 | Bellon Labor Sa Roger | Nouveaux derives de l'oxazole, leur preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2677477B1 (fr) * | 1991-06-06 | 1993-08-20 | Bellon Labor Sa Roger | Nouveaux derives de l'oxazole leur preparation, leur utilisation et les compositions pharmaceutiques qui les contiennent. |
| MXPA05011276A (es) * | 2003-04-21 | 2006-01-24 | Daiichi Seiyaku Co | Derivado heterociclico de cinco miembros. |
| FR2866340B1 (fr) * | 2004-02-13 | 2006-11-24 | Sanofi Synthelabo | Derives d'oxazole, leur preparation et leur utilisation en therapeutique. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2166118A (en) * | 1936-10-03 | 1939-07-18 | Du Pont | Insecticidal compositions containing heterocyclic amides |
| US3401120A (en) * | 1965-10-23 | 1968-09-10 | Gaf Corp | Corrosion inhibitors |
| US3578671A (en) * | 1967-11-06 | 1971-05-11 | Wyeth John & Brother Ltd | Oxazoles |
| IT1053674B (it) * | 1968-01-31 | 1981-10-10 | Istituto Farmacobiologico Sero | N amidino carbossiamidi ossazoliche ad azione natriuretica |
-
1970
- 1970-03-05 IT IT21550/70A patent/IT1043805B/it active
-
1971
- 1971-02-26 CH CH283971A patent/CH555846A/it not_active IP Right Cessation
- 1971-03-01 US US119832A patent/US3869455A/en not_active Expired - Lifetime
- 1971-03-04 DE DE19712110363 patent/DE2110363A1/de active Pending
- 1971-03-04 CA CA106,905A patent/CA949580A/en not_active Expired
- 1971-03-05 FR FR7107751A patent/FR2085675B1/fr not_active Expired
- 1971-03-05 JP JP46011584A patent/JPS504663B1/ja active Pending
- 1971-04-19 GB GB22899/71A patent/GB1293702A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5262540A (en) * | 1989-12-20 | 1993-11-16 | Bristol-Myers Squibb Company | [2(4,5-diaryl-2 oxazoyl substituted phenoxy alkanoic acid and esters |
Also Published As
| Publication number | Publication date |
|---|---|
| CA949580A (en) | 1974-06-18 |
| FR2085675A1 (cg-RX-API-DMAC7.html) | 1971-12-31 |
| GB1293702A (en) | 1972-10-25 |
| CH555846A (it) | 1974-11-15 |
| JPS504663B1 (cg-RX-API-DMAC7.html) | 1975-02-22 |
| FR2085675B1 (cg-RX-API-DMAC7.html) | 1974-04-12 |
| US3869455A (en) | 1975-03-04 |
| IT1043805B (it) | 1980-02-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |