JPS6045866B2 - 安息香酸誘導体、その製造法ならびにそれを有郊成分とする解熱鎮痛剤、消炎剤および去痰剤 - Google Patents

安息香酸誘導体、その製造法ならびにそれを有郊成分とする解熱鎮痛剤、消炎剤および去痰剤

Info

Publication number: JPS6045866B2
Authority: JP; Japan
Prior art keywords: formula; group; general formula; benzoic acid; tables
Prior art date: 1981-02-06
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

Application number

JP57012523A

Other languages

English (en)

Japanese (ja)

Other versions

JPS57144244A (en

Inventor

カルロ・ミラニ

ギオバンニ・マリア・カルミナチ

アツチリオ・ソベ−ラ

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

SERUBI E CO SpA

Original Assignee

SERUBI E CO SpA

Priority date (The priority date 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 date listed.)

1981-02-06

Filing date

1982-01-27

Publication date

1985-10-12

1982-01-27 Application filed by SERUBI E CO SpA filed Critical SERUBI E CO SpA

1982-09-06 Publication of JPS57144244A publication Critical patent/JPS57144244A/ja

1985-10-12 Publication of JPS6045866B2 publication Critical patent/JPS6045866B2/ja

Status Expired legal-status Critical Current

Links

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229940121363 anti-inflammatory agent Drugs 0.000 title claims description 10
230000001754 anti-pyretic effect Effects 0.000 title description 6
239000002221 antipyretic Substances 0.000 title description 2
150000001558 benzoic acid derivatives Chemical class 0.000 title description 2
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238000006243 chemical reaction Methods 0.000 claims description 17
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238000000034 method Methods 0.000 claims description 17
239000002904 solvent Substances 0.000 claims description 16
IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
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239000011261 inert gas Substances 0.000 claims description 3
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125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
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238000000921 elemental analysis Methods 0.000 description 4
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HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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238000004809 thin layer chromatography Methods 0.000 description 3
238000007039 two-step reaction Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
206010030113 Oedema Diseases 0.000 description 2
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JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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238000011047 acute toxicity test Methods 0.000 description 2
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WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
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125000005916 2-methylpentyl group Chemical group 0.000 description 1
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BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
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150000004649 carbonic acid derivatives Chemical class 0.000 description 1
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239000012046 mixed solvent Substances 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
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125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
235000014571 nuts Nutrition 0.000 description 1
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210000002345 respiratory system Anatomy 0.000 description 1
230000028327 secretion Effects 0.000 description 1
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235000011803 sesame oil Nutrition 0.000 description 1
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239000012177 spermaceti Substances 0.000 description 1
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238000010998 test method Methods 0.000 description 1
231100000820 toxicity test Toxicity 0.000 description 1
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Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/265—Esters, e.g. nitroglycerine, selenocyanates of carbonic, thiocarbonic, or thiocarboxylic acids, e.g. thioacetic acid, xanthogenic acid, trithiocarbonic acid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/60—Salicylic acid; Derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
- C07C65/05—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring o-Hydroxy carboxylic acids
- C07C65/10—Salicylic acid
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
- C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/12—Preparation of carboxylic acid esters from asymmetrical anhydrides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
- C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
- C07C69/157—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/78—Benzoic acid esters
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/94—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/96—Esters of carbonic or haloformic acids

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Emergency Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

JP57012523A 1981-02-06 1982-01-27 安息香酸誘導体、その製造法ならびにそれを有郊成分とする解熱鎮痛剤、消炎剤および去痰剤 Expired JPS6045866B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT19562/81A IT1194790B (it)	1981-02-06	1981-02-06	Derivati dell'acido salicilico
IT19562A/81		1981-02-06

Publications (2)

Publication Number	Publication Date
JPS57144244A JPS57144244A (en)	1982-09-06
JPS6045866B2 true JPS6045866B2 (ja)	1985-10-12

Family

ID=11159081

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP57012523A Expired JPS6045866B2 (ja)	1981-02-06	1982-01-27	安息香酸誘導体、その製造法ならびにそれを有郊成分とする解熱鎮痛剤、消炎剤および去痰剤

Country Status (7)

Country	Link
JP (1)	JPS6045866B2 (de)
AT (1)	AT375635B (de)
DE (1)	DE3148424C2 (de)
ES (1)	ES507643A0 (de)
FR (1)	FR2499559B1 (de)
IT (1)	IT1194790B (de)
ZA (1)	ZA818149B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2953832B1 (fr) *	2009-12-10	2012-01-13	Galderma Res & Dev	Derives de nouveaux peroxydes, leur procede de preparation et leur utilisation en medecine humaine ainsi qu'en cosmetique pour le traitement ou la prevention de l'acne
CN117126072B (zh) *	2023-08-24	2025-12-30	中国药科大学	一种含酯链pd-1/pd-l1小分子抑制剂及其制备方法和应用

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3681445A (en) *	1968-01-19	1972-08-01	Merck & Co Inc	Substituted phenyl benzoic acid compounds
US4216340A (en) *	1979-05-02	1980-08-05	Merck & Co., Inc.	Preparation of 5-(2,4-difluorophenyl)salicylic acid and derivatives

1981
- 1981-02-06 IT IT19562/81A patent/IT1194790B/it active
- 1981-11-24 ZA ZA818149A patent/ZA818149B/xx unknown
- 1981-12-02 ES ES507643A patent/ES507643A0/es active Granted
- 1981-12-08 DE DE3148424A patent/DE3148424C2/de not_active Expired
- 1981-12-10 AT AT0529081A patent/AT375635B/de not_active IP Right Cessation
1982
- 1982-01-27 JP JP57012523A patent/JPS6045866B2/ja not_active Expired
- 1982-01-27 FR FR8201267A patent/FR2499559B1/fr not_active Expired

Also Published As

Publication number	Publication date
JPS57144244A (en)	1982-09-06
ATA529081A (de)	1984-01-15
DE3148424C2 (de)	1985-12-05
FR2499559B1 (fr)	1986-04-25
ES8207115A1 (es)	1982-09-01
ES507643A0 (es)	1982-09-01
FR2499559A1 (fr)	1982-08-13
IT1194790B (it)	1988-09-28
AT375635B (de)	1984-08-27
DE3148424A1 (de)	1982-09-09
IT8119562A0 (it)	1981-02-06
ZA818149B (en)	1982-10-27

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DE3306006C2 (de)	1992-02-06
JPH01139528A (ja)	1989-06-01	抗潰瘍剤
BE898278A (fr)	1984-05-22	Benzoxazines antipsychotiques.
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DE3035086C2 (de)	1991-01-03
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US4826837A (en)	1989-05-02	Cinnoline-carboxamides and process for their preparation
JPS6045866B2 (ja)	1985-10-12	安息香酸誘導体、その製造法ならびにそれを有郊成分とする解熱鎮痛剤、消炎剤および去痰剤
US4748184A (en)	1988-05-31	Aryl substituted aminomethyl benzene derivatives having antiarrhythmic utility
JP2661892B2 (ja)	1997-10-08	Ｎ−アリールアルキルフェニルアセトアミド化合物
JPH0692915A (ja)	1994-04-05	１，２−ジアミノシクロブテン−３，４−ジオン誘導体及びその用途
EP0083222B1 (de)	1986-02-26	Chinolinessigsäuren und diese enthaltende pharmazeutische Zubereitungen
US4521538A (en)	1985-06-04	Ester of the 1-methyl-5-p-toluoylpyrrole-2-acetic acid having antiinflammatory, mucolytic and antitussive properties, process for its preparation and pharmaceutical compositions containing them
JPS6399057A (ja)	1988-04-30	グリシン誘導体
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JPH03163042A (ja)	1991-07-15	カルコン誘導体
Holland et al.	1976	Cinnoline-3-propionic acids, a new series of orally active antiallergic substances
US4432991A (en)	1984-02-21	Therapeutically active 3-amino-1-phenyl(and substituted phenyl)-2-pyrazolines
KR910002371B1 (ko)	1991-04-20	치환된 디-t-부틸페놀 및 이것을 함유한 약학적 조성물
US4073929A (en)	1978-02-14	3-(2-Substitutedbenzimidazolyl) alanines