JPS6056131B2 - テレフタル酸アミド誘導体及びその塩 - Google Patents
テレフタル酸アミド誘導体及びその塩Info
- Publication number
- JPS6056131B2 JPS6056131B2 JP6893178A JP6893178A JPS6056131B2 JP S6056131 B2 JPS6056131 B2 JP S6056131B2 JP 6893178 A JP6893178 A JP 6893178A JP 6893178 A JP6893178 A JP 6893178A JP S6056131 B2 JPS6056131 B2 JP S6056131B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- melting point
- same manner
- elemental analysis
- water
- 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
- 150000003839 salts Chemical class 0.000 title claims 2
- JMHSCWJIDIKGNZ-UHFFFAOYSA-N 4-carbamoylbenzoic acid Chemical class NC(=O)C1=CC=C(C(O)=O)C=C1 JMHSCWJIDIKGNZ-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- 238000000921 elemental analysis Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 7
- LDQMZKBIBRAZEA-UHFFFAOYSA-N 2,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C(N)=C1 LDQMZKBIBRAZEA-UHFFFAOYSA-N 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000003266 anti-allergic effect Effects 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- XSMJEZONDSZQKY-UHFFFAOYSA-N 4-amino-2-[(4-carboxybenzoyl)amino]benzoic acid Chemical compound NC1=CC=C(C(O)=O)C(NC(=O)C=2C=CC(=CC=2)C(O)=O)=C1 XSMJEZONDSZQKY-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 229960004050 aminobenzoic acid Drugs 0.000 description 3
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229940080818 propionamide Drugs 0.000 description 3
- 229940086681 4-aminobenzoate Drugs 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical group OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical group OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
- PVDBFTHSLKGRSB-UHFFFAOYSA-N 2-[(4-ethoxycarbonylbenzoyl)amino]-4-(2-methylpropanoylamino)benzoic acid Chemical compound C1=CC(C(=O)OCC)=CC=C1C(=O)NC1=CC(NC(=O)C(C)C)=CC=C1C(O)=O PVDBFTHSLKGRSB-UHFFFAOYSA-N 0.000 description 1
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
- COOGCYDPBSRHJC-UHFFFAOYSA-N 4-(propanoylamino)-2-[(4-propan-2-yloxycarbonylbenzoyl)amino]benzoic acid Chemical compound CCC(=O)NC1=CC=C(C(O)=O)C(NC(=O)C=2C=CC(=CC=2)C(=O)OC(C)C)=C1 COOGCYDPBSRHJC-UHFFFAOYSA-N 0.000 description 1
- WFZMGMGJYJSKFW-UHFFFAOYSA-N 4-[(5-amino-2-ethoxycarbonylphenyl)carbamoyl]benzoic acid Chemical compound CCOC(=O)C1=CC=C(N)C=C1NC(=O)C1=CC=C(C(O)=O)C=C1 WFZMGMGJYJSKFW-UHFFFAOYSA-N 0.000 description 1
- OWBIWBRHQSXFGK-UHFFFAOYSA-N 4-amino-2-[(4-butoxycarbonylbenzoyl)amino]benzoic acid Chemical compound C1=CC(C(=O)OCCCC)=CC=C1C(=O)NC1=CC(N)=CC=C1C(O)=O OWBIWBRHQSXFGK-UHFFFAOYSA-N 0.000 description 1
- GZEOMCWZTIUAEZ-UHFFFAOYSA-N 4-amino-2-[(4-ethoxycarbonylbenzoyl)amino]benzoic acid Chemical compound C1=CC(C(=O)OCC)=CC=C1C(=O)NC1=CC(N)=CC=C1C(O)=O GZEOMCWZTIUAEZ-UHFFFAOYSA-N 0.000 description 1
- APWJUWSQSWFNHO-UHFFFAOYSA-N 4-amino-2-[(4-methoxycarbonylbenzoyl)amino]benzoic acid Chemical compound C1=CC(C(=O)OC)=CC=C1C(=O)NC1=CC(N)=CC=C1C(O)=O APWJUWSQSWFNHO-UHFFFAOYSA-N 0.000 description 1
- YPJRVRRZXKLBRD-UHFFFAOYSA-N 4-amino-2-[(4-propoxycarbonylbenzoyl)amino]benzoic acid Chemical compound C1=CC(C(=O)OCCC)=CC=C1C(=O)NC1=CC(N)=CC=C1C(O)=O YPJRVRRZXKLBRD-UHFFFAOYSA-N 0.000 description 1
- SVWCVXFHTHCJJB-UHFFFAOYSA-N 4-methylpentanoyl chloride Chemical compound CC(C)CCC(Cl)=O SVWCVXFHTHCJJB-UHFFFAOYSA-N 0.000 description 1
- UEALKTCRMBVTFN-UHFFFAOYSA-N 4-nitroanthranilic acid Chemical compound NC1=CC([N+]([O-])=O)=CC=C1C(O)=O UEALKTCRMBVTFN-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- -1 methoxycarbonylbenzamido-4-isobutyramidobenzoic acid Chemical compound 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003503 terephthalic acid derivatives Chemical class 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (21)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6893178A JPS6056131B2 (ja) | 1978-06-09 | 1978-06-09 | テレフタル酸アミド誘導体及びその塩 |
| 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. |
| BE2/57861A BE876850A (fr) | 1978-06-09 | 1979-06-08 | Monoamides derives de l'acide terephtalique, procede pour leur preparation et agent anallergique prepare a partir de ceux-ci |
| CS397279A CS226189B2 (cs) | 1978-06-09 | 1979-06-08 | Způsob přípravy monoamidového derivátu tereftalové kyseliny |
| 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 |
| DE19792923298 DE2923298A1 (de) | 1978-06-09 | 1979-06-08 | Terephthalsaeuremonoamide, verfahren zu ihrer herstellung und ihre verwendung bei der behandlung allergischer erkrankungen |
| ES481416A ES481416A1 (es) | 1978-06-09 | 1979-06-08 | Un procedimiento para la preparacion de un derivado monoami-da de acido tereftalico. |
| HU79CU163A HU176077B (en) | 1978-06-09 | 1979-06-08 | Process for preparing terephtalic acid monoamide derivatives |
| CH540379A CH642059A5 (de) | 1978-06-09 | 1979-06-08 | Terephthalsaeuremonoamid-derivate, verfahren zu deren herstellung und diese enthaltendes antiallergisches pharmazeutisches praeparat. |
| GB7920005A GB2023576B (en) | 1978-06-09 | 1979-06-08 | Terephthalic acid amides |
| AR276872A AR225896A1 (es) | 1978-06-09 | 1979-06-08 | Procedimiento de preparacion de un derivado de acido 2-monotereftalamido-4-alcanomidobenzoico |
| 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 |
| MX1085679U MX7154E (es) | 1978-06-09 | 1979-06-11 | Procedimiento para preparar derivados de monoamida del acido tereftalico |
| MX79101219U MX5711E (es) | 1978-06-09 | 1979-06-11 | Procedimiento para la preparacion de derivados amidicos del acido tereftalico |
| SU792775640A SU1015821A3 (ru) | 1978-06-09 | 1979-07-08 | Способ получени моноамидных производных терефталевой кислоты |
| 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 |
|---|---|---|---|
| JP6893178A JPS6056131B2 (ja) | 1978-06-09 | 1978-06-09 | テレフタル酸アミド誘導体及びその塩 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54163540A JPS54163540A (en) | 1979-12-26 |
| JPS6056131B2 true JPS6056131B2 (ja) | 1985-12-09 |
Family
ID=13387889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6893178A Expired JPS6056131B2 (ja) | 1978-06-09 | 1978-06-09 | テレフタル酸アミド誘導体及びその塩 |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS6056131B2 (cs) |
| BE (1) | BE876850A (cs) |
| CS (1) | CS226189B2 (cs) |
| SU (1) | SU1015821A3 (cs) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53146405A (en) * | 1977-05-26 | 1978-12-20 | Obayashi Gumi Kk | Method of drawing pile out |
-
1978
- 1978-06-09 JP JP6893178A patent/JPS6056131B2/ja not_active Expired
-
1979
- 1979-06-08 CS CS397279A patent/CS226189B2/cs unknown
- 1979-06-08 BE BE2/57861A patent/BE876850A/xx not_active IP Right Cessation
- 1979-07-08 SU SU792775640A patent/SU1015821A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54163540A (en) | 1979-12-26 |
| CS226189B2 (cs) | 1984-03-19 |
| BE876850A (fr) | 1979-10-01 |
| SU1015821A3 (ru) | 1983-04-30 |
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