SE424442B - Estrar av alfa-(n-etyl-n-n-propylamin)-smorsyra till anvendning som mellanprodukter vid framstellning av terapeutiskt aktiva foreningar - Google Patents
Estrar av alfa-(n-etyl-n-n-propylamin)-smorsyra till anvendning som mellanprodukter vid framstellning av terapeutiskt aktiva foreningarInfo
- Publication number
- SE424442B SE424442B SE7801062A SE7801062A SE424442B SE 424442 B SE424442 B SE 424442B SE 7801062 A SE7801062 A SE 7801062A SE 7801062 A SE7801062 A SE 7801062A SE 424442 B SE424442 B SE 424442B
- Authority
- SE
- Sweden
- Prior art keywords
- ethyl
- therapeutically active
- preparation
- intermediates
- estars
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000000543 intermediate Substances 0.000 title description 3
- 239000002253 acid Substances 0.000 title 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 229940008406 diethyl sulfate Drugs 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 238000003747 Grignard reaction Methods 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- YAQLSKVCTLCIIE-UHFFFAOYSA-N 2-bromobutyric acid Chemical compound CCC(Br)C(O)=O YAQLSKVCTLCIIE-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 101000710187 Conus radiatus Conantokin-R Proteins 0.000 description 1
- 241000238557 Decapoda Species 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XIMFCGSNSKXPBO-UHFFFAOYSA-N ethyl 2-bromobutanoate Chemical compound CCOC(=O)C(Br)CC XIMFCGSNSKXPBO-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UFQQDNMQADCHGH-UHFFFAOYSA-N methyl 2-bromobutanoate Chemical compound CCC(Br)C(=O)OC UFQQDNMQADCHGH-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7801062A SE424442B (sv) | 1978-01-30 | 1978-01-30 | Estrar av alfa-(n-etyl-n-n-propylamin)-smorsyra till anvendning som mellanprodukter vid framstellning av terapeutiskt aktiva foreningar |
| NO790116A NO790116L (no) | 1978-01-30 | 1979-01-15 | Mellomprodukter for bruk ved fremstilling av terapeutisk virksomme forbindelser |
| DK20879A DK20879A (da) | 1978-01-30 | 1979-01-18 | Dialkylaminalkansyreestere til fremstilling af terapeutisk viriksomme forbindelser |
| ES477051A ES477051A1 (es) | 1978-01-30 | 1979-01-22 | Un procedimiento para preparar derivados del acido butirico. |
| IT47765/79A IT1116533B (it) | 1978-01-30 | 1979-01-24 | Procedimento per la preparazione di intermedi e di composti terapeuticamente attivi e prodotto ottenuto |
| FI790229A FI790229A7 (fi) | 1978-01-30 | 1979-01-24 | Nya mellanprodukter anvaendbara foer framstaellning av terapeutiskt verksamma foereningar |
| NL7900643A NL7900643A (nl) | 1978-01-30 | 1979-01-26 | Als tussenprodukten geschikte verbindingen voor de bereiding van therapeutisch actieve verbindingen. |
| AT0059279A AT367393B (de) | 1978-01-30 | 1979-01-26 | Verfahren zur herstellung von neuen alfa-aminobutters[urealkylestern, ihren salzen und optischen antipoden |
| JP881679A JPS54112821A (en) | 1978-01-30 | 1979-01-30 | Novel compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7801062A SE424442B (sv) | 1978-01-30 | 1978-01-30 | Estrar av alfa-(n-etyl-n-n-propylamin)-smorsyra till anvendning som mellanprodukter vid framstellning av terapeutiskt aktiva foreningar |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7801062L SE7801062L (sv) | 1979-07-31 |
| SE424442B true SE424442B (sv) | 1982-07-19 |
Family
ID=20333796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7801062A SE424442B (sv) | 1978-01-30 | 1978-01-30 | Estrar av alfa-(n-etyl-n-n-propylamin)-smorsyra till anvendning som mellanprodukter vid framstellning av terapeutiskt aktiva foreningar |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS54112821A (da) |
| AT (1) | AT367393B (da) |
| DK (1) | DK20879A (da) |
| ES (1) | ES477051A1 (da) |
| FI (1) | FI790229A7 (da) |
| IT (1) | IT1116533B (da) |
| NL (1) | NL7900643A (da) |
| NO (1) | NO790116L (da) |
| SE (1) | SE424442B (da) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3401969A (en) * | 1966-10-28 | 1968-09-17 | Forest J. Neel | Safety chain locking device |
| US3544154A (en) * | 1968-07-26 | 1970-12-01 | Gailerd B Ford | Dump truck spreader chain mounting |
-
1978
- 1978-01-30 SE SE7801062A patent/SE424442B/sv unknown
-
1979
- 1979-01-15 NO NO790116A patent/NO790116L/no unknown
- 1979-01-18 DK DK20879A patent/DK20879A/da not_active Application Discontinuation
- 1979-01-22 ES ES477051A patent/ES477051A1/es not_active Expired
- 1979-01-24 IT IT47765/79A patent/IT1116533B/it active
- 1979-01-24 FI FI790229A patent/FI790229A7/fi unknown
- 1979-01-26 AT AT0059279A patent/AT367393B/de not_active IP Right Cessation
- 1979-01-26 NL NL7900643A patent/NL7900643A/xx not_active Application Discontinuation
- 1979-01-30 JP JP881679A patent/JPS54112821A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FI790229A7 (fi) | 1979-07-31 |
| NL7900643A (nl) | 1979-08-01 |
| AT367393B (de) | 1982-06-25 |
| IT7947765A0 (it) | 1979-01-24 |
| IT1116533B (it) | 1986-02-10 |
| SE7801062L (sv) | 1979-07-31 |
| ATA59279A (de) | 1981-11-15 |
| DK20879A (da) | 1979-07-31 |
| ES477051A1 (es) | 1979-06-16 |
| NO790116L (no) | 1979-07-31 |
| JPS54112821A (en) | 1979-09-04 |
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