JPS6125022B2 - - Google Patents
Info
- Publication number
- JPS6125022B2 JPS6125022B2 JP14969678A JP14969678A JPS6125022B2 JP S6125022 B2 JPS6125022 B2 JP S6125022B2 JP 14969678 A JP14969678 A JP 14969678A JP 14969678 A JP14969678 A JP 14969678A JP S6125022 B2 JPS6125022 B2 JP S6125022B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- general formula
- present
- compound
- propionamide
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229940080818 propionamide Drugs 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- JMHSCWJIDIKGNZ-UHFFFAOYSA-N 4-carbamoylbenzoic acid Chemical class NC(=O)C1=CC=C(C(O)=O)C=C1 JMHSCWJIDIKGNZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- -1 aliphatic alcohols Chemical class 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
- IBEWUERKHSBEKP-UHFFFAOYSA-N 4-(4-oxo-3,1-benzoxazin-2-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC2=CC=CC=C2C(=O)O1 IBEWUERKHSBEKP-UHFFFAOYSA-N 0.000 description 1
- DSTFDDPNDAKZBU-UHFFFAOYSA-N 4-[[2-butoxycarbonyl-5-(propanoylamino)phenyl]carbamoyl]benzoic acid Chemical compound CCCCOC(=O)C1=CC=C(NC(=O)CC)C=C1NC(=O)C1=CC=C(C(O)=O)C=C1 DSTFDDPNDAKZBU-UHFFFAOYSA-N 0.000 description 1
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- UDEWPOVQBGFNGE-UHFFFAOYSA-N benzoic acid n-propyl ester Natural products CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 description 1
- 150000005130 benzoxazines Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (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 (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14969678A JPS5576853A (en) | 1978-12-05 | 1978-12-05 | Preparation of derivative of terephthalic acid amide |
| DK214679A DK214679A (da) | 1978-06-09 | 1979-05-23 | Terephthalsyremonoamid derivater fremgangsmaade til deres fremstilling samt antiallergiske midler indeholdende disse |
| IT7968172A IT1165210B (it) | 1978-06-09 | 1979-05-31 | Derivati della mono ammide dell acido tereftalico procedimento per la loro preparazione ed agente anti allergico ottenuto da detti derivati |
| US06/044,687 US4221814A (en) | 1978-06-09 | 1979-06-01 | Terephthalic acid monoamide derivatives, process for preparing the same, and an anti-allergic agent prepared from the same |
| NL7904466A NL7904466A (nl) | 1978-06-09 | 1979-06-07 | Werkwijze voor de bereiding van een anti-allergisch middel met een monoamidederivaat van tereftaalzuur als actieve stof en de bereiding van de actieve stof, evenals het gevormde geneesmiddel. |
| FR7914734A FR2428026A1 (fr) | 1978-06-09 | 1979-06-08 | Derives de monoamides de l'acide terephtalique, leur procede de preparation et leur application en therapeutique |
| AR276872A AR225896A1 (es) | 1978-06-09 | 1979-06-08 | Procedimiento de preparacion de un derivado de acido 2-monotereftalamido-4-alcanomidobenzoico |
| CS644181A CS226196B2 (en) | 1978-12-05 | 1979-06-08 | Method of preparing monoamide derivative of terephtalic acid |
| ES481416A ES481416A1 (es) | 1978-06-09 | 1979-06-08 | Un procedimiento para la preparacion de un derivado monoami-da de acido tereftalico. |
| CH540379A CH642059A5 (de) | 1978-06-09 | 1979-06-08 | Terephthalsaeuremonoamid-derivate, verfahren zu deren herstellung und diese enthaltendes antiallergisches pharmazeutisches praeparat. |
| DE19792923298 DE2923298A1 (de) | 1978-06-09 | 1979-06-08 | Terephthalsaeuremonoamide, verfahren zu ihrer herstellung und ihre verwendung bei der behandlung allergischer erkrankungen |
| GB7920005A GB2023576B (en) | 1978-06-09 | 1979-06-08 | Terephthalic acid amides |
| HU79CU163A HU176077B (en) | 1978-06-09 | 1979-06-08 | Process for preparing terephtalic acid monoamide derivatives |
| CA000329379A CA1140571A (en) | 1978-06-09 | 1979-06-08 | Terephthalic acid monoamide derivatives, process for preparing the same, and an anti-allergic agent prepared from the same |
| SE7905025A SE445830B (sv) | 1978-06-09 | 1979-06-08 | Tereftalsyramonoamidderivat, forfarande for framstellning derav och antiallergiskt medel |
| SU792860202A SU1026651A3 (ru) | 1978-12-05 | 1979-12-04 | Способ получени моноамидных производных терефталевой кислоты или их фармацевтически приемлемых солей |
| ES489475A ES489475A0 (es) | 1978-06-09 | 1980-03-12 | Un procedimiento para la preparacion de un derivado de mo- noamida del acido tereftalico |
| AR284485A AR225072A1 (es) | 1978-06-09 | 1981-02-27 | Procedimiento de preparacion de un derivado de acido 2-monotereftalamido-4-alcanamidobenzoico |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14969678A JPS5576853A (en) | 1978-12-05 | 1978-12-05 | Preparation of derivative of terephthalic acid amide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5576853A JPS5576853A (en) | 1980-06-10 |
| JPS6125022B2 true JPS6125022B2 (enrdf_load_stackoverflow) | 1986-06-13 |
Family
ID=15480808
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14969678A Granted JPS5576853A (en) | 1978-06-09 | 1978-12-05 | Preparation of derivative of terephthalic acid amide |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5576853A (enrdf_load_stackoverflow) |
| CS (1) | CS226196B2 (enrdf_load_stackoverflow) |
| SU (1) | SU1026651A3 (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63162667U (enrdf_load_stackoverflow) * | 1987-04-14 | 1988-10-24 |
-
1978
- 1978-12-05 JP JP14969678A patent/JPS5576853A/ja active Granted
-
1979
- 1979-06-08 CS CS644181A patent/CS226196B2/cs unknown
- 1979-12-04 SU SU792860202A patent/SU1026651A3/ru active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63162667U (enrdf_load_stackoverflow) * | 1987-04-14 | 1988-10-24 |
Also Published As
| Publication number | Publication date |
|---|---|
| SU1026651A3 (ru) | 1983-06-30 |
| CS226196B2 (en) | 1984-03-19 |
| JPS5576853A (en) | 1980-06-10 |
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