JPS60105651A - ２−ヒドロキシ−５−〔１−ヒドロキシ−２−（４−フエニル−２−ブチル）アミノエチル〕ベンズアミドの製造法 - Google Patents
２−ヒドロキシ−５−〔１−ヒドロキシ−２−（４−フエニル−２−ブチル）アミノエチル〕ベンズアミドの製造法Info
- Publication number
- JPS60105651A JPS60105651A JP59202903A JP20290384A JPS60105651A JP S60105651 A JPS60105651 A JP S60105651A JP 59202903 A JP59202903 A JP 59202903A JP 20290384 A JP20290384 A JP 20290384A JP S60105651 A JPS60105651 A JP S60105651A
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- benzamide
- phenyl
- active ingredient
- hydrochloride
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- SGUAFYQXFOLMHL-UHFFFAOYSA-N 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide Chemical compound C=1C=C(O)C(C(N)=O)=CC=1C(O)CNC(C)CCC1=CC=CC=C1 SGUAFYQXFOLMHL-UHFFFAOYSA-N 0.000 title description 9
- 239000000203 mixture Substances 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 238000005804 alkylation reaction Methods 0.000 claims description 11
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 7
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- -1 (N-( 1-Methyl-3-phenylpropyl)amino)acetyl benzamide Chemical compound 0.000 claims description 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- WECUIGDEWBNQJJ-UHFFFAOYSA-N 4-phenylbutan-2-amine Chemical compound CC(N)CCC1=CC=CC=C1 WECUIGDEWBNQJJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003708 ampul Substances 0.000 claims description 3
- 230000002152 alkylating effect Effects 0.000 claims 1
- 238000010276 construction Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 229960001632 labetalol Drugs 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000029936 alkylation Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 108060003345 Adrenergic Receptor Proteins 0.000 description 2
- 102000017910 Adrenergic receptor Human genes 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000012790 confirmation Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 2
- 239000010421 standard material Substances 0.000 description 2
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 101150056612 PPIA gene Proteins 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical compound Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004821 distillation Methods 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
- 150000004820 halides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229940100688 oral solution Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- 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
- C07C231/00—Preparation of carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- 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
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/30—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT23005/83A IT1194406B (it) | 1983-09-27 | 1983-09-27 | Procedimento per la preparazione di 2-idrossi-5-01-idrossi-2-((4-fenil-2-butil)ammino) etil benzammide |
| IT23005A/83 | 1983-09-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS60105651A true JPS60105651A (ja) | 1985-06-11 |
Family
ID=11202777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59202903A Pending JPS60105651A (ja) | 1983-09-27 | 1984-09-27 | ２−ヒドロキシ−５−〔１−ヒドロキシ−２−（４−フエニル−２−ブチル）アミノエチル〕ベンズアミドの製造法 |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS60105651A (enrdf_load_stackoverflow) |
| BE (1) | BE900663A (enrdf_load_stackoverflow) |
| CH (1) | CH661923A5 (enrdf_load_stackoverflow) |
| DE (1) | DE3435349A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2552427B1 (enrdf_load_stackoverflow) |
| GB (1) | GB2149399B (enrdf_load_stackoverflow) |
| IT (1) | IT1194406B (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017098520A1 (en) * | 2015-12-09 | 2017-06-15 | prscDAVALURI RAMAMOHAN RAO | Process for the preparation of labetalol hydrochloride |
| CN112225674B (zh) * | 2020-10-28 | 2021-12-03 | 天津大学 | 盐酸拉贝洛尔晶型化合物及其制备方法和应用 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4843341A (enrdf_load_stackoverflow) * | 1971-10-02 | 1973-06-22 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1266058A (enrdf_load_stackoverflow) * | 1969-07-08 | 1972-03-08 | ||
| ZA794872B (en) * | 1978-09-20 | 1980-11-26 | Schering Corp | A phenylalkylaminoethylsalicylamide,its preparation and pharmaceutical compositions containing it |
-
1983
- 1983-09-27 IT IT23005/83A patent/IT1194406B/it active
-
1984
- 1984-09-24 BE BE0/213712A patent/BE900663A/fr not_active IP Right Cessation
- 1984-09-24 GB GB08424100A patent/GB2149399B/en not_active Expired
- 1984-09-25 CH CH4607/84A patent/CH661923A5/it not_active IP Right Cessation
- 1984-09-26 DE DE19843435349 patent/DE3435349A1/de active Granted
- 1984-09-27 JP JP59202903A patent/JPS60105651A/ja active Pending
- 1984-09-27 FR FR8414820A patent/FR2552427B1/fr not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4843341A (enrdf_load_stackoverflow) * | 1971-10-02 | 1973-06-22 |
Also Published As
| Publication number | Publication date |
|---|---|
| IT8323005A1 (it) | 1985-03-27 |
| BE900663A (fr) | 1985-01-16 |
| IT8323005A0 (it) | 1983-09-27 |
| FR2552427B1 (fr) | 1988-03-25 |
| DE3435349C2 (enrdf_load_stackoverflow) | 1989-09-21 |
| GB8424100D0 (en) | 1984-10-31 |
| DE3435349A1 (de) | 1985-04-18 |
| GB2149399A (en) | 1985-06-12 |
| FR2552427A1 (fr) | 1985-03-29 |
| CH661923A5 (it) | 1987-08-31 |
| IT1194406B (it) | 1988-09-22 |
| GB2149399B (en) | 1987-05-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6054482A (en) | Lactam-free amino acids | |
| CA2293247C (en) | 4-phenylpiperidine compounds | |
| KR100830002B1 (ko) | 시부트라민의 무기산염 | |
| US4017539A (en) | Biguanide compounds and anti-diabetic compositions | |
| EP1846360A1 (en) | A sulphonic acid salt of sibutramine | |
| HUP0001878A2 (hu) | (R)-3-(N,N-diciklobutil-amino)-8-fluor-3,4-dihidro-2H-1-benzopirán-5-karboxamid-hidrogén tartarát, eljárás előállítására és ezt tartalmazó gyógyszerkészítmények | |
| CA2164296C (en) | Heterocyclic chemistry | |
| JPS60105651A (ja) | ２−ヒドロキシ−５−〔１−ヒドロキシ−２−（４−フエニル−２−ブチル）アミノエチル〕ベンズアミドの製造法 | |
| US5587377A (en) | Terazosin crystalline polymorph and pharmaceutical compositions thereof | |
| EP0113910B1 (en) | Isocarbostyril derivatives, processes for their preparation and pharmaceutical compositions containing them | |
| ZA200109775B (en) | Polymorphs of a crystalline azabicyclo (2,2,2) octan-3-amine citrate and their pharmaceutical compositions. | |
| US20210323929A1 (en) | Purified Detomidine, Process of Preparing and Methods of Use | |
| GB2068963A (en) | Basic ethers of 4-hydroxy-benzophenones acting as beta-blocking agents and relevant preparation processes | |
| IL47060A (en) | Quaternary ammonium salts of n-dialkylaminoalkyl-n-(2-indanyl)anilines | |
| JP2003535845A (ja) | プロパノールアミノテトラリン類、その製造及びそれらを含む組成物 | |
| EP1620388A1 (en) | Sibutramine free base in crystalline form and its pharmaceutical use | |
| JP2005530746A (ja) | カルベジロールファーマソルブ溶媒和物 | |
| CN116768879A (zh) | 一种抗真菌药物的合成方法 | |
| KR20110095545A (ko) | (ｓ)-리바스티그민 오로트산염 및 이를 포함하는 약제학적 조성물 | |
| EP1073625A1 (en) | Tilidine mesylate, processes for its preparation and pharmaceutical composition thereof | |
| GB2336840A (en) | Tilidine embonate | |
| HK1046284B (en) | Polymorphs of crystalline azabicyclo(2,2,2) octan-3-aminecitrate and their pharmaceutical compositions | |
| HK1025575B (en) | A new salt | |
| JPS6249263B2 (enrdf_load_stackoverflow) |