JPS60231639A - ベンズアミド誘導体の調製方法 - Google Patents

ベンズアミド誘導体の調製方法

Info

Publication number: JPS60231639A
Authority: JP; Japan
Prior art keywords: hydroxy; benzamide; compound; following formula; formula
Prior art date: 1984-01-20
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

Application number

JP597885A

Other languages

English (en)

Japanese (ja)

Inventor

パル　バゴ

ヨゼフ　レイテル

フリジエス　ゲルゲンイ

タマス　フオドル

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.)

Egyt Gyogyszervegyeszeti Gyar

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

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.)

1984-01-20

Filing date

1985-01-18

Publication date

1985-11-18

1985-01-18 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1985-11-18 Publication of JPS60231639A publication Critical patent/JPS60231639A/ja

Status Pending legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title description 9
150000003936 benzamides Chemical class 0.000 title description 2
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 48
150000001875 compounds Chemical class 0.000 claims description 32
238000000034 method Methods 0.000 claims description 32
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 16
-1 dibenzylamino Chemical group 0.000 claims description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
239000003054 catalyst Substances 0.000 claims description 12
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 10
125000001841 imino group Chemical group [H]N=* 0.000 claims description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
238000005984 hydrogenation reaction Methods 0.000 claims description 5
WOEISFSYHVAQTR-UHFFFAOYSA-N 5-(2-amino-1-hydroxyethyl)-2-hydroxybenzamide Chemical compound NCC(O)C1=CC=C(O)C(C(N)=O)=C1 WOEISFSYHVAQTR-UHFFFAOYSA-N 0.000 claims description 4
238000002955 isolation Methods 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
239000000203 mixture Substances 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
229910052763 palladium Inorganic materials 0.000 claims description 3
229910052697 platinum Inorganic materials 0.000 claims description 3
DNLPQXRWAKCKPX-UHFFFAOYSA-N 2-carbamoyl-4-[2-(dibenzylazaniumyl)acetyl]phenolate Chemical compound C1=C(O)C(C(=O)N)=CC(C(=O)CN(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=C1 DNLPQXRWAKCKPX-UHFFFAOYSA-N 0.000 claims description 2
239000002904 solvent Substances 0.000 claims 1
239000010902 straw Substances 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
239000003610 charcoal Substances 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
239000002253 acid Substances 0.000 description 4
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
229910052705 radium Inorganic materials 0.000 description 3
HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
RVLDETSVEUQULS-UHFFFAOYSA-N 5-(2-amino-1-hydroxyethyl)-2-hydroxybenzamide;hydrochloride Chemical compound Cl.NCC(O)C1=CC=C(O)C(C(N)=O)=C1 RVLDETSVEUQULS-UHFFFAOYSA-N 0.000 description 2
BWHOZHOGCMHOBV-UHFFFAOYSA-N Benzalacetone Natural products CC(=O)C=CC1=CC=CC=C1 BWHOZHOGCMHOBV-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
239000002585 base Substances 0.000 description 2
SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical compound Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
125000000468 ketone group Chemical group 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
229910003446 platinum oxide Inorganic materials 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
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
LWAQTCWTCCNHJR-UHFFFAOYSA-N 5-acetyl-2-hydroxybenzamide Chemical compound CC(=O)C1=CC=C(O)C(C(N)=O)=C1 LWAQTCWTCCNHJR-UHFFFAOYSA-N 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000002262 Schiff base Substances 0.000 description 1
150000004753 Schiff bases Chemical class 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000021615 conjugation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000000994 depressogenic effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP597885A 1984-01-20 1985-01-18 ベンズアミド誘導体の調製方法 Pending JPS60231639A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU23484A HU190867B (en)	1984-01-20	1984-01-20	Process for preparing 2-hydroxy-5-/1-hydroxy-2-/1-methyl-3-phenyl-propyl/-amino/ethyl/-benzamide and pharmaceutically acceptable salts thereof
HU2251/234/84		1984-01-20

Publications (1)

Publication Number	Publication Date
JPS60231639A true JPS60231639A (ja)	1985-11-18

Family

ID=10948617

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP597885A Pending JPS60231639A (ja)	1984-01-20	1985-01-18	ベンズアミド誘導体の調製方法

Country Status (18)

Country	Link
JP (1)	JPS60231639A (cs)
AT (1)	AT390612B (cs)
CA (1)	CA1239938A (cs)
CH (1)	CH662810A5 (cs)
CS (1)	CS249536B2 (cs)
DD (1)	DD228245A5 (cs)
DE (1)	DE3501582A1 (cs)
DK (1)	DK26185A (cs)
ES (1)	ES8608481A1 (cs)
FI (1)	FI83635C (cs)
FR (1)	FR2558465B1 (cs)
GB (1)	GB2152931B (cs)
HU (1)	HU190867B (cs)
NL (1)	NL8500119A (cs)
NO (1)	NO165918C (cs)
PT (1)	PT79844B (cs)
SE (1)	SE8500236L (cs)
SU (1)	SU1521281A3 (cs)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1247370A (en) *	1968-12-31	1971-09-22	Allen & Hanburys Ltd	Glyoxals and production thereof
ZA794872B (en) *	1978-09-20	1980-11-26	Schering Corp	A phenylalkylaminoethylsalicylamide,its preparation and pharmaceutical compositions containing it

1984
- 1984-01-20 HU HU23484A patent/HU190867B/hu not_active IP Right Cessation
- 1984-12-17 CH CH598584A patent/CH662810A5/de not_active IP Right Cessation
1985
- 1985-01-18 DK DK26185A patent/DK26185A/da not_active Application Discontinuation
- 1985-01-18 PT PT7984485A patent/PT79844B/pt unknown
- 1985-01-18 SU SU853837675A patent/SU1521281A3/ru active
- 1985-01-18 DD DD27264985A patent/DD228245A5/de not_active IP Right Cessation
- 1985-01-18 FI FI850229A patent/FI83635C/fi not_active IP Right Cessation
- 1985-01-18 CA CA000472445A patent/CA1239938A/en not_active Expired
- 1985-01-18 NO NO850225A patent/NO165918C/no unknown
- 1985-01-18 FR FR8500702A patent/FR2558465B1/fr not_active Expired
- 1985-01-18 AT AT11685A patent/AT390612B/de not_active IP Right Cessation
- 1985-01-18 GB GB08501246A patent/GB2152931B/en not_active Expired
- 1985-01-18 DE DE19853501582 patent/DE3501582A1/de not_active Withdrawn
- 1985-01-18 ES ES540121A patent/ES8608481A1/es not_active Expired
- 1985-01-18 JP JP597885A patent/JPS60231639A/ja active Pending
- 1985-01-18 CS CS37785A patent/CS249536B2/cs unknown
- 1985-01-18 NL NL8500119A patent/NL8500119A/nl not_active Application Discontinuation
- 1985-06-06 SE SE8500236A patent/SE8500236L/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
DK26185D0 (da)	1985-01-18
ATA11685A (de)	1989-11-15
NL8500119A (nl)	1985-08-16
SU1521281A3 (ru)	1989-11-07
FI83635C (fi)	1991-08-12
DK26185A (da)	1985-07-21
CA1239938A (en)	1988-08-02
PT79844A (en)	1985-02-01
FR2558465A1 (fr)	1985-07-26
DD228245A5 (de)	1985-10-09
NO850225L (no)	1985-07-22
CH662810A5 (de)	1987-10-30
FR2558465B1 (fr)	1988-08-26
DE3501582A1 (de)	1985-08-01
NO165918C (no)	1991-05-02
SE8500236L (sv)	1985-07-21
HU190867B (en)	1986-11-28
CS249536B2 (en)	1987-03-12
FI850229A0 (fi)	1985-01-18
PT79844B (en)	1986-10-23
ES8608481A1 (es)	1986-07-16
ES540121A0 (es)	1986-07-16
AT390612B (de)	1990-06-11
SE8500236D0 (sv)	1985-01-18
NO165918B (no)	1991-01-21
GB2152931A (en)	1985-08-14
FI83635B (fi)	1991-04-30
GB8501246D0 (en)	1985-02-20
GB2152931B (en)	1987-03-18
HUT36779A (en)	1985-10-28
FI850229L (fi)	1985-07-21

Publication	Publication Date	Title
JP4056093B2 (ja)	2008-03-05	ペルヒドロイソインドール置換体の製造方法
EP0432504B1 (de)	1994-06-08	Verfahren zur Herstellung von 1-(Aminomethyl)cyclohexanessigsäure
US4824953A (en)	1989-04-25	Multi-step process for producing 5-hydroxy-N-(6-oxo-piperidyl-methyl)-2-(2,2,2-trifluoro-ethoxy)-benzamide and derivatives
JP2792046B2 (ja)	1998-08-27	光学活性なアミン−ホウ素系化合物、それを有効成分とする不斉還元剤ならびにそれを用いる光学活性化合物の製造方法
JPS5820957B2 (ja)	1983-04-26	シンキナルブテノ−ルアミンユウドウタイノシンキセイゾウホウ
JPS59181257A (ja)	1984-10-15	ウレイドベンズアミド誘導体
US4277420A (en)	1981-07-07	Ephedrine and pseudoephedrine precursors
US3048633A (en)	1962-08-07	N-lower alkyl-2-(benzyloxatedphenyl)-glycolamide
DE2409313A1 (de)	1974-09-12	Neue pyrrolyl-verbindungen und verfahren zu ihrer herstellung
JP2810465B2 (ja)	1998-10-15	Ｎ−メチル−４−ｔ−ブチルベンジルアミンの製造法
EP0286991B1 (en)	1993-08-18	Process for preparing fluorine-substituted alicyclic diols
US3239563A (en)	1966-03-08	Reduction of 1-phenyl-nitropropane-1, 3-diol
JPH01186848A (ja)	1989-07-26	４−アルキルベンジルアミン類の製造法
JPH04217943A (ja)	1992-08-07	Ｎ−（２−アミノ−３，５−ジブロモベンジル）−トランス−４−アミノ−シクロヘキサノール及びその製造方法
GB2201417A (en)	1988-09-01	4-(2-Pyrimidinyl)-piperazine derivatives
JPS63264568A (ja)	1988-11-01	インドリン類の製造方法
DE2414772C3 (de)	1979-08-30	H33-Diphenylpropyl)-2-methyl-3phenylaziridin und Verfahren zu seiner Herstellung
GB2152931A (en)	1985-08-14	Benzamide derivatives
JPS5846515B2 (ja)	1983-10-17	インド−ル誘導体の製造方法
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JP3544694B2 (ja)	2004-07-21	Ｎ−ｔｅｒｔ−ブチル−２−ピペラジンカルボキサミド類の製造法
Williams	2001	United States Patent No
JPH03176496A (ja)	1991-07-31	フェロセニル誘導体及びその利用
EP0582929A1 (de)	1994-02-16	Verfahren zur Herstellung von Aminophenylacetaten
JPS63218637A (ja)	1988-09-12	ｃｉｓ−クロチルアルコ−ルの製造法