IL38412A - Alpha-cyano-3,4,5-trialkoxycinnamic acid derivatives - Google Patents
Alpha-cyano-3,4,5-trialkoxycinnamic acid derivativesInfo
- Publication number
- IL38412A IL38412A IL38412A IL3841271A IL38412A IL 38412 A IL38412 A IL 38412A IL 38412 A IL38412 A IL 38412A IL 3841271 A IL3841271 A IL 3841271A IL 38412 A IL38412 A IL 38412A
- Authority
- IL
- Israel
- Prior art keywords
- general formula
- process according
- general
- same
- preparation
- Prior art date
Links
- 239000002253 acid Substances 0.000 title description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000003610 charcoal Substances 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 2
- 150000003230 pyrimidines Chemical class 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 206010027783 Moaning Diseases 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 235000013985 cinnamic acid Nutrition 0.000 claims 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid group Chemical class C(C=CC1=CC=CC=C1)(=O)O WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
- C07D239/49—Two nitrogen atoms with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE792122D BE792122A (fr) | 1971-12-01 | Procede de preparation de benzyl-pyrimidines | |
| IL38412A IL38412A (en) | 1971-12-20 | 1971-12-20 | Alpha-cyano-3,4,5-trialkoxycinnamic acid derivatives |
| IE1597/72A IE37186B1 (en) | 1971-12-01 | 1972-11-20 | Improvements in and relating to the production of benzyl-pyrimidines |
| NO4340/72A NO136195C (no) | 1971-12-01 | 1972-11-27 | Fremgangsm}te ved fremstilling av 2,4-diamino-5-benzylpyrimidiner. |
| AT1008672A AT320619B (de) | 1971-12-20 | 1972-11-27 | Verfahren zur Herstellung von neuen α-Cyan-Zimtsäure und α-Cyandihydrozimtsäure-Derivaten |
| SE7215519A SE407061B (sv) | 1971-12-01 | 1972-11-28 | Forfarande for framstellning av bensylpyrimidiner |
| DE2264389*A DE2264389A1 (de) | 1971-12-20 | 1972-11-28 | Verfahren zur herstellung von 2,4diamino-5-benzyl-pyrimidinen |
| CH1731972A CH588450A5 (de) | 1971-12-20 | 1972-11-28 | |
| CA157,702A CA977347A (en) | 1971-12-20 | 1972-11-28 | Benzylcyano-acids and amides |
| DE19722258239 DE2258239A1 (de) | 1971-12-20 | 1972-11-28 | Zimtsaeure- und dihydrozimtsaeurederivate und verfahren zu ihrer herstellung |
| OA54766A OA04279A (fr) | 1971-12-01 | 1972-11-29 | Procédé de préparation de benzyl-pyrimidines. |
| NL7216222A NL7216222A (de) | 1971-12-20 | 1972-11-30 | |
| DK598972A DK132703C (da) | 1971-12-01 | 1972-11-30 | Fremgangsmade til fremstilling af 2,4-diamino-5-benzylpyrimidiner |
| GB5559772A GB1406307A (en) | 1971-12-01 | 1972-12-01 | Production of benzylpyrimidines |
| SE7513881A SE7513881L (sv) | 1971-12-01 | 1975-12-09 | Mellanprodukter, avsedda att anvendas for framstellning av antibakteriella bensylpyrimidiner |
| HK456/76*UA HK45676A (en) | 1971-12-01 | 1976-07-15 | Improvements in and relating to the production of benzylpyrimidines |
| US05/722,355 USRE29467E (en) | 1971-12-20 | 1976-09-13 | Benzylcyano-amides |
| KE2660A KE2660A (en) | 1971-12-01 | 1976-09-15 | Improvements in and relating to the production of benzylpyrimidines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL38412A IL38412A (en) | 1971-12-20 | 1971-12-20 | Alpha-cyano-3,4,5-trialkoxycinnamic acid derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL38412A0 IL38412A0 (en) | 1972-02-29 |
| IL38412A true IL38412A (en) | 1977-02-28 |
Family
ID=11046257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL38412A IL38412A (en) | 1971-12-01 | 1971-12-20 | Alpha-cyano-3,4,5-trialkoxycinnamic acid derivatives |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT320619B (de) |
| CA (1) | CA977347A (de) |
| CH (1) | CH588450A5 (de) |
| DE (2) | DE2258239A1 (de) |
| IL (1) | IL38412A (de) |
| NL (1) | NL7216222A (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5025575A (de) * | 1973-07-03 | 1975-03-18 | ||
| DE2623170C2 (de) * | 1976-05-22 | 1982-03-11 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von α-Cyanzimtaldehyd-Derivaten und 3,4,5-Trimethoxy-α-Cyanzimtaldehyd |
| JPH078851B2 (ja) * | 1985-07-29 | 1995-02-01 | 鐘淵化学工業株式会社 | ３−フエニルチオメチルスチレン誘導体 |
| US5202341A (en) * | 1987-03-11 | 1993-04-13 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Hydroxystyrene compounds having tyrosine kinase inhibiting activity |
| DE3874257T2 (de) * | 1987-03-11 | 1993-02-11 | Kanegafuchi Chemical Ind | Hydroxystyren-derivate. |
| US5089516A (en) * | 1987-03-11 | 1992-02-18 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | 1-phenyl-3,5-pyrazolidinedione hydroxystyrene compounds which have tyrosine kinase inhibiting activity |
| US5063243A (en) * | 1988-04-28 | 1991-11-05 | Suntory, Ltd. | Derivative of caffeic acid and pharmaceutical composition containing the same |
-
1971
- 1971-12-20 IL IL38412A patent/IL38412A/en unknown
-
1972
- 1972-11-27 AT AT1008672A patent/AT320619B/de not_active IP Right Cessation
- 1972-11-28 CA CA157,702A patent/CA977347A/en not_active Expired
- 1972-11-28 DE DE19722258239 patent/DE2258239A1/de active Pending
- 1972-11-28 DE DE2264389*A patent/DE2264389A1/de not_active Ceased
- 1972-11-28 CH CH1731972A patent/CH588450A5/xx not_active IP Right Cessation
- 1972-11-30 NL NL7216222A patent/NL7216222A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CH588450A5 (de) | 1977-06-15 |
| AT320619B (de) | 1975-02-25 |
| DE2258239A1 (de) | 1973-06-28 |
| DE2264389A1 (de) | 1973-09-27 |
| IL38412A0 (en) | 1972-02-29 |
| CA977347A (en) | 1975-11-04 |
| NL7216222A (de) | 1973-06-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU460626A3 (ru) | Способ получени винкамина или его производных | |
| IL38412A (en) | Alpha-cyano-3,4,5-trialkoxycinnamic acid derivatives | |
| CA1074322A (en) | 2-hydroxymethyl-3-hydroxy-6-(1-hydroxy-2-t-butylaminoethyl) pyridine via hydrogenolysis of its benzylidene acetal | |
| EP0213850B1 (de) | Cyanatabspaltung von Pergolidzwischenverbindung | |
| US3947405A (en) | Process for making neohesperidine dihydrochalcone | |
| EP0678501B1 (de) | Verfahren zur Herstellung von N-Chloracetylglutamin | |
| JP2682705B2 (ja) | ２，６−ジクロロフェニルアミノベンゼン酢酸誘導体及びジフェニルアミン誘導体の製造方法。 | |
| US2441935A (en) | Imidazolidones and method for their manufacture | |
| US3185686A (en) | Pyrazine derivatives | |
| US4764614A (en) | Process for preparing (S)(+)-4,4'(methyl-1,2-ethanediyl)-bis(2,6-piperazinedione) | |
| US4539428A (en) | Preparation of diaminodiphenyl ethers | |
| USRE29467E (en) | Benzylcyano-amides | |
| US2557041A (en) | Synthesis of tryptophane | |
| KR0141482B1 (ko) | 0-카르복시피리딜-및 0-카르복시퀴놀릴이미다졸리논의 개선된 제조방법 | |
| US3058992A (en) | Intermediates for the preparation of | |
| US3910984A (en) | Benzylcyano-amides | |
| DK170372B1 (da) | Fremgangsmåde til fremstilling af 4-substituerede indolin-2-oner | |
| KR950008971B1 (ko) | α-N-[(히포크산틴-9-일)펜틸옥시카르보닐]알기닌의 제조방법 | |
| KR0163042B1 (ko) | 4-아미노-5-헥센산의 제조방법 | |
| SU504476A3 (ru) | Способ получени -бис-(2-/3,4-диоксифенил/-2-оксиэтил)-гексаметилендиамина | |
| US4182880A (en) | 1,8-Naphthyridine compounds and process for preparing the same | |
| US4841092A (en) | Preparation of tris(2-cyanoethyl)amine | |
| SU567402A3 (ru) | Способ получени производных хинолина или их солей | |
| JPS60181058A (ja) | シアノメチル‐（２‐シアノ‐エチル）‐（３‐ヒドロキシ‐プロピル）‐アミン及びその製法、及び１‐（３‐ヒドロキシ‐プロピル）‐１，４‐ジアゼパン及び１，４‐ビス‐〔３‐（３，４，５‐トリメトキシ‐ベンゾイルオキシ）‐プロピル〕‐ジアゼパンの製法 | |
| US3296267A (en) | Preparation of 2, 3-dihydroxy-6-quinoxaline carboxylic acid |