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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Title cpds. are of formula: (where R1 and R2 are each H, halogen, lower alkyl or alkoxy; R3 and R4 are each lower alkoxy; Y is OH or amino gp. opt. alkyl-substd., the broken alpha,beta-line may denote a double bond; if the double bond is absent, the alpha and beta C atoms carry H atoms instead; with the proviso that in the presence of a double bond R1 is not H, R2-4 are not methoxy gps., and Y is not OH) and they are produced by reacting the corresp. benzaldehyde with NC-CH2COY in the presence of a basic condensation catalyst, and opt. hydrogenating the product.
[DE2258239A1]
Description
acid derivatives Plantex cinnamic present invention relates to and of general formula I in which and or different stands Tor and stand for the satae or different lover alkoxy Y stands for a or an unsubstituted or amino group and the dotted line designates either an additional bond or hydrogen atoms at the carbon ding The compounds of formula I are valuable intermediates in a process for the preparation of certain pyrimidines vhich in turn are easily transformed to pharmaceutically valuable as described in Israel Patent Specification The present invention consists also in a process for the preparation of compounds of general formula I an aldehyde of general formula II in vhich and have the same meaning as above is reacted in the presence of a suitable basic catalyst vith a compound of eneral formula III which Y has the same meaning as above to yield a compound of general formula in and have the same meaning as if the compound of general formula IV is ticaljy with a suitable in a suitable inert solvent to yield the desired compound of general formula V in which She basic caalys used in the reaction step is preferably a secondary amine a or sodium or preferably potassium ste in an inert solvent such tetrohydrofuranj Said step is preferably performed at between temperatures are indicated herein in degrees As catalyst the step there may be or platinized As suitable solvents there may be mentioned ethyl The present invention consists also in a process for preparation of pyriaidines in which a compound of general formula V without a solvent or in the presence of a suitable reacted with guanidine to yield a compound of general formula VI in which and have the same meaning as The with guanidine when being performed in an inert is performed preferably in an alcohol such as The invention will now be illustrated with reference to the following examples without being limited by Example 1 A mixture of 100 g of and g of cyanoacetic acid in 1 of water containing 21 g of sodium hydroxide was stirred for 2 hours at The clear solution obtained was 120 cc of 5N hydrochloric acid were added and after additional cooling the precipitate was filtered off and washed with 200 of The crude material was dried at and used in the hydrogenation step without It melted at The yield of acid was 126 g Example 2 100 g of obtained in She mixture was hydrogenated at atmospheric pressure until the absorption of hydrogen had The catalyst removed and 175 cc of hydrochloric acid were She precipitate filtered washed 200 cc of water and dried vacuo at for 10 hours to yield g of acid A pure recrystaHized from chloroform melted at Example 100 g of and 44 g of acetamide dissolved in 300 of dry pyridine at To this solution 10 oc of piporidine added and the mixture was heated at the above temperature with stirring for 2 The reaction mixture was cooled at room filtered off and the tate was washed on the filter with 50 cc of cold product was dried at to yield of This product wasused for the hydrogenation step without further A recrystaHiaed from melted at Example 4 100 g of obtained in example 3 were dissolved in of a mixture of and g of of charcoal were The mixture was at atmospheric pressure until the absorption of hydrogen had catalyst was removed and the solvent was evaporated under residue was crystallized from ethyl acetate to after drying at for 6 g of To a solution of 23 g of sodium in 90 g of guanidine carbonate was added and the mixture vas stirred for 13 minutes at She precipitated carbonate vas filtered off with over and the solids washed 200 co of To this guanidine solution in methanol vere added 132 g prepared as described in example solution vas for 6 hours and the methanol was distilled off in residue vas dissolved in 300 of water and the product by the addition of hydrochloric acid to pH After allowin to cool at for 2 hours the white solid filtered off and washed with 40 cc of She product was dried at for 12 hours to of colourless e 100g A mixture 60 g of freshly guanidine was heated at for 1 hour with occasional reaction mixture was in 75 cc of hot water and the solution was She product was precipitated by aiding to the clear hydrochloric to pH After allowing to cool at for 4 hours the solid was filtered off and washed with 30 cc of She product was at for 12 hours to obtain g Of a compound which was identical with the compound obtained in example insufficientOCRQuality
Claims (1)
1. 6 Claims cinnamic acids and amides of general ormula I in which stands for stands for lower and stand for the same or different lower alkoxy Y stands for a hydroxy or an unsubstituted or amino group and the dotted line designates either an additional bond or hydrogen atoms at the carbon excluding A process for the preparation of compounds of general formula I as defined in Claim 1 an aldehyde of general formula II in which and have the same meaning as in Claim 1 is reacted in the presence of a suitable basic catalyst with a which Y has sane moaning as in 1 to yield a compound of general I in which and Y have the same meaning as in Claim if the compound of general formula IV is tically with a suitable catalyst in a suitable inert solvent to yield the desired of general formula V in which Y have the same as in Claim A process according to 5 wherein the basic catalyst of reaction step a secondary or potassium hydroxide or a A process according to or wherein reaction step is performed in an inert an an piperidine or A process according to any of Claims 5 to 7 wherein the hydrogenation catalyst is charcoal and the inert A process for preparation of of general formula as defined in Claim substantially as hereinbefore described with reference to the Examples 1 to Compounds of general formula as defined in Claim 1 whenever prepared by the process according to any of 5 to A process for the preparation of in which and Y have the same as in Claim 1 without a solvent or in the presence of suitable reacted to yield a compound of general in which have the same as in Claim A process according to Claim wherein the reaction la performed in an alcoholic A process for the preparation pyrimidines of general VI as defined in stantially as hereinbefore described with reference to examples of general formula VI 11 whenever prepared by the process according o any of claims to the Applicante Yitzhak Hess insufficientOCRQuality
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE792122D BE792122A (en) | 1971-12-01 | BENZYL-PYRIMIDINES PREPARATION PROCESS | |
| 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 |
| AT1008672A AT320619B (en) | 1971-12-20 | 1972-11-27 | Process for the preparation of new α-cyano-cinnamic acid and α-cyandihydrocinnamic acid derivatives |
| NO4340/72A NO136195C (en) | 1971-12-01 | 1972-11-27 | PROCEDURES FOR THE PREPARATION OF 2,4-DIAMINO-5-BENZYLPYRIMIDINES. |
| CA157,702A CA977347A (en) | 1971-12-20 | 1972-11-28 | Benzylcyano-acids and amides |
| DE2264389*A DE2264389A1 (en) | 1971-12-20 | 1972-11-28 | PROCESS FOR THE PREPARATION OF 2,4DIAMINO-5-BENZYL-PYRIMIDINES |
| SE7215519A SE407061B (en) | 1971-12-01 | 1972-11-28 | PROCEDURE FOR THE PREPARATION OF BENZYLPYRIMIDINES |
| DE19722258239 DE2258239A1 (en) | 1971-12-20 | 1972-11-28 | Cinnamic and dihydrocinnamic acid derivs - used as starting materials for antibacterial 2,4-diamino-5-benzylpyrimidines |
| CH1731972A CH588450A5 (en) | 1971-12-20 | 1972-11-28 | |
| OA54766A OA04279A (en) | 1971-12-01 | 1972-11-29 | Process for the preparation of benzyl-pyrimidines. |
| NL7216222A NL7216222A (en) | 1971-12-20 | 1972-11-30 | |
| DK598972A DK132703C (en) | 1971-12-01 | 1972-11-30 | PROCEDURE FOR THE PREPARATION OF 2,4-DIAMINO-5-BENZYLPYRIMIDINES |
| GB5559772A GB1406307A (en) | 1971-12-01 | 1972-12-01 | Production of benzylpyrimidines |
| SE7513881A SE7513881L (en) | 1971-12-01 | 1975-12-09 | INTERMEDIATE PRODUCTS INTENDED FOR THE PREPARATION OF ANTIBACTERIAL BENZYLPYRIMIDINES |
| 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 (en) |
| CA (1) | CA977347A (en) |
| CH (1) | CH588450A5 (en) |
| DE (2) | DE2258239A1 (en) |
| IL (1) | IL38412A (en) |
| NL (1) | NL7216222A (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5025575A (en) * | 1973-07-03 | 1975-03-18 | ||
| DE2623170C2 (en) * | 1976-05-22 | 1982-03-11 | Basf Ag, 6700 Ludwigshafen | Process for the preparation of α-cyano cinnamaldehyde derivatives and 3,4,5-trimethoxy-α-cyano cinnamic aldehyde |
| JPH078851B2 (en) * | 1985-07-29 | 1995-02-01 | 鐘淵化学工業株式会社 | 3-phenylthiomethylstyrene derivative |
| JP2539504B2 (en) * | 1987-03-11 | 1996-10-02 | 鐘淵化学工業株式会社 | Hydroxystyrene derivative |
| US5202341A (en) * | 1987-03-11 | 1993-04-13 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Hydroxystyrene compounds having tyrosine kinase inhibiting activity |
| 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 |
| KR900016098A (en) * | 1988-04-28 | 1990-11-12 | 사하루 게이 죠오 | Derivatives of Caffeic Acid and Pharmaceutical Compositions Containing the Same |
-
1971
- 1971-12-20 IL IL38412A patent/IL38412A/en unknown
-
1972
- 1972-11-27 AT AT1008672A patent/AT320619B/en not_active IP Right Cessation
- 1972-11-28 DE DE19722258239 patent/DE2258239A1/en active Pending
- 1972-11-28 CA CA157,702A patent/CA977347A/en not_active Expired
- 1972-11-28 CH CH1731972A patent/CH588450A5/xx not_active IP Right Cessation
- 1972-11-28 DE DE2264389*A patent/DE2264389A1/en not_active Ceased
- 1972-11-30 NL NL7216222A patent/NL7216222A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AT320619B (en) | 1975-02-25 |
| NL7216222A (en) | 1973-06-22 |
| CH588450A5 (en) | 1977-06-15 |
| DE2258239A1 (en) | 1973-06-28 |
| CA977347A (en) | 1975-11-04 |
| DE2264389A1 (en) | 1973-09-27 |
| IL38412A0 (en) | 1972-02-29 |
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