NO134372B - - Google Patents

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Info

Publication number: NO134372B
Authority: NO; Norway
Prior art keywords: water; parts; ether; ethanol; palladium
Prior art date: 1971-10-19

Application number

NO3714/72A

Other languages

English (en)

Norwegian (no)

Other versions

NO134372C (fi

Inventor

D Henschler

J Wagner

H Hampel

Original Assignee

Klinge Co Chem Pharm Fab

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.)

1971-10-19

Filing date

1972-10-17

Publication date

1976-06-21

1971-10-19 Priority claimed from DE19712152058 external-priority patent/DE2152058C3/de

1972-10-17 Application filed by Klinge Co Chem Pharm Fab filed Critical Klinge Co Chem Pharm Fab

1976-06-21 Publication of NO134372B publication Critical patent/NO134372B/no

1976-09-29 Publication of NO134372C publication Critical patent/NO134372C/no

Links

KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
239000003054 catalyst Substances 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
238000000034 method Methods 0.000 claims description 9
-1 pivaloyloxy Chemical group 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
150000001875 compounds Chemical class 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
238000005984 hydrogenation reaction Methods 0.000 description 10
239000000047 product Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
230000008018 melting Effects 0.000 description 8
238000002844 melting Methods 0.000 description 8
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 6
125000002252 acyl group Chemical group 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000000243 solution Substances 0.000 description 5
UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 4
239000008280 blood Substances 0.000 description 4
210000004369 blood Anatomy 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
230000000873 masking effect Effects 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
229960003424 phenylacetic acid Drugs 0.000 description 3
239000003279 phenylacetic acid Substances 0.000 description 3
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 2
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
230000004060 metabolic process Effects 0.000 description 2
230000002085 persistent effect Effects 0.000 description 2
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 2
230000002035 prolonged effect Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
YRCWQPVGYLYSOX-UHFFFAOYSA-N synephrine Chemical compound CNCC(O)C1=CC=C(O)C=C1 YRCWQPVGYLYSOX-UHFFFAOYSA-N 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 description 1
VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
KWUJFMFEIDIIQI-UHFFFAOYSA-N 3-(benzylamino)-1-(4-hydroxyphenyl)propan-1-one Chemical compound C1=CC(O)=CC=C1C(=O)CCNCC1=CC=CC=C1 KWUJFMFEIDIIQI-UHFFFAOYSA-N 0.000 description 1
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000371 Esterases Proteins 0.000 description 1
238000012404 In vitro experiment Methods 0.000 description 1
241000700159 Rattus Species 0.000 description 1
239000000150 Sympathomimetic Substances 0.000 description 1
SNTGWYJPRFEDHW-UHFFFAOYSA-N [2,3-diphenyl-6-[2-(2-phenylethylamino)acetyl]phenyl] acetate Chemical compound C1(=CC=CC=C1)C=1C(=C(C=CC1C1=CC=CC=C1)C(CNCCC1=CC=CC=C1)=O)OC(C)=O SNTGWYJPRFEDHW-UHFFFAOYSA-N 0.000 description 1
FJAHKCRRQLIPBP-UHFFFAOYSA-N [3-[3-(benzylamino)propanoyl]-5-(2,2-dimethylpropanoyloxy)phenyl] 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC1=CC(OC(=O)C(C)(C)C)=CC(C(=O)CCNCC=2C=CC=CC=2)=C1 FJAHKCRRQLIPBP-UHFFFAOYSA-N 0.000 description 1
GNLYYQYVTORTMI-UHFFFAOYSA-N [3-[3-(benzylamino)propanoyl]phenyl] 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC1=CC=CC(C(=O)CCNCC=2C=CC=CC=2)=C1 GNLYYQYVTORTMI-UHFFFAOYSA-N 0.000 description 1
NUHGTCXLUJRWFQ-UHFFFAOYSA-N [3-[3-(benzylamino)propanoyl]phenyl] 2-phenylacetate Chemical compound C=1C=CC(C(=O)CCNCC=2C=CC=CC=2)=CC=1OC(=O)CC1=CC=CC=C1 NUHGTCXLUJRWFQ-UHFFFAOYSA-N 0.000 description 1
UEZDDSIYXRQSFU-UHFFFAOYSA-N [3-[4-(benzylamino)butanoyl]phenyl] 2-phenylacetate Chemical compound C=1C=CC(C(=O)CCCNCC=2C=CC=CC=2)=CC=1OC(=O)CC1=CC=CC=C1 UEZDDSIYXRQSFU-UHFFFAOYSA-N 0.000 description 1
BJEIDEHGENHVJB-UHFFFAOYSA-N [4-[3-(benzylamino)propanoyl]phenyl] 2,2-dimethylpropanoate Chemical compound C1=CC(OC(=O)C(C)(C)C)=CC=C1C(=O)CCNCC1=CC=CC=C1 BJEIDEHGENHVJB-UHFFFAOYSA-N 0.000 description 1
UZXKYBMHNPFNBQ-UHFFFAOYSA-N [4-[3-(benzylamino)propanoyl]phenyl] 2-phenylacetate Chemical compound C=1C=C(C(=O)CCNCC=2C=CC=CC=2)C=CC=1OC(=O)CC1=CC=CC=C1 UZXKYBMHNPFNBQ-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003245 coal Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
230000000058 esterolytic effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
229960003684 oxedrine Drugs 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229960001802 phenylephrine Drugs 0.000 description 1
ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical class NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
230000001975 sympathomimetic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
- C07C215/30—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/14—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on a carbon-to-carbon unsaturated bond in organic compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Emergency Medicine (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO3714/72A 1971-10-19 1972-10-17 NO134372C (fi)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19712152058 DE2152058C3 (de)		1971-10-19	O-Acyl-phenoläthanolamine und Verfahren zu deren Herstellung Klinge Pharma GmbH & Co, 8000 München

Publications (2)

Publication Number	Publication Date
NO134372B true NO134372B (fi)	1976-06-21
NO134372C NO134372C (fi)	1976-09-29

Family

ID=5822789

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO3714/72A NO134372C (fi)	1971-10-19	1972-10-17

Country Status (15)

Country	Link
US (1)	US4085270A (fi)
AR (1)	AR196206A1 (fi)
AT (1)	AT317183B (fi)
BE (1)	BE790234A (fi)
BR (1)	BR7207279D0 (fi)
CH (1)	CH564517A5 (fi)
DD (1)	DD99776A1 (fi)
FI (1)	FI55988C (fi)
FR (1)	FR2158232B1 (fi)
GB (1)	GB1358973A (fi)
HU (1)	HU164582B (fi)
LU (1)	LU66312A1 (fi)
NL (1)	NL7213759A (fi)
NO (1)	NO134372C (fi)
SE (1)	SE391332B (fi)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3809714A (en) *	1972-08-31	1974-05-07	Interx Research Corp	Novel ester of ((methylamino)methyl) benzyl alcohol
US3868461A (en) *	1972-11-22	1975-02-25	Interx Research Corp	Ester of 3,4-dihydroxy-alpha (isopropylamino) methyl benzyl alcohol, composition and anti-asthma use thereof
FR2469411A1 (fr) *	1979-11-15	1981-05-22	Science Union & Cie	Nouveaux derives de la piperidylbenzimidazolinone, leurs procedes de preparation et les compositions pharmaceutiques les renfermant
DE3163871D1 (en)	1980-07-09	1984-07-05	Draco Ab	1-(dihydroxyphenyl)-2-amino-ethanol derivatives; preparation, compositions and intermediates
GB0315929D0 (en) *	2003-07-08	2003-08-13	Koninkl Philips Electronics Nv	Display device
CN101921198B (zh) *	2010-08-18	2013-04-24	潍坊幸福药业有限公司	一种盐酸依替福林的制备方法
WO2016060564A1 (en) *	2014-10-14	2016-04-21	Brains Online Holding B.V. Et All	Body sculpting
ES2954361T3 (es) *	2017-09-08	2023-11-21	Insignis Therapeutics Inc	Métodos de uso de dipivefrina

1972
- 1972-10-11 FI FI2816/72A patent/FI55988C/fi active
- 1972-10-11 NL NL7213759A patent/NL7213759A/xx not_active Application Discontinuation
- 1972-10-12 SE SE7213184A patent/SE391332B/xx unknown
- 1972-10-13 US US05/297,416 patent/US4085270A/en not_active Expired - Lifetime
- 1972-10-17 LU LU66312A patent/LU66312A1/xx unknown
- 1972-10-17 HU HUCE900A patent/HU164582B/hu unknown
- 1972-10-17 DD DD166276A patent/DD99776A1/xx unknown
- 1972-10-17 NO NO3714/72A patent/NO134372C/no unknown
- 1972-10-17 AT AT887572A patent/AT317183B/de not_active IP Right Cessation
- 1972-10-18 BR BR7279/72A patent/BR7207279D0/pt unknown
- 1972-10-18 GB GB4809872A patent/GB1358973A/en not_active Expired
- 1972-10-18 CH CH1521272A patent/CH564517A5/xx not_active IP Right Cessation
- 1972-10-18 BE BE790234D patent/BE790234A/xx not_active IP Right Cessation
- 1972-10-18 FR FR7236899A patent/FR2158232B1/fr not_active Expired
- 1972-10-19 AR AR244726A patent/AR196206A1/es active

Also Published As

Publication number	Publication date
DD99776A1 (fi)	1973-08-20
US4085270A (en)	1978-04-18
AR196206A1 (es)	1973-12-10
FR2158232B1 (fi)	1975-10-17
FI55988B (fi)	1979-07-31
FR2158232A1 (fi)	1973-06-15
GB1358973A (en)	1974-07-03
CH564517A5 (fi)	1975-07-31
AT317183B (de)	1974-08-12
DE2152058B2 (de)	1976-03-04
HU164582B (fi)	1974-03-28
NL7213759A (fi)	1973-04-25
NO134372C (fi)	1976-09-29
FI55988C (fi)	1979-11-12
SE391332B (sv)	1977-02-14
LU66312A1 (fi)	1973-01-23
BR7207279D0 (pt)	1973-09-25
DE2152058A1 (de)	1973-04-26
BE790234A (fr)	1973-02-15

Publication	Publication Date	Title
NO134372B (fi)	1976-06-21
Fried et al.	1950	The hypotensive principles of Veratrum viride
US3553258A (en)	1971-01-05	Phenylalanine compounds
LU84770A1 (fr)	1984-11-28	Benzoazacycloalkyl-spiro-imidazolidines,leur preparation et leur application en therapeutique
Kubota et al.	1966	The Structure and Total Synthesis of Takatonine1
US5504089A (en)	1996-04-02	2-hydroxyalkyl-benzimidazoles, -quinazolines and -benzothiazoles as potassium channel agonists
US3998835A (en)	1976-12-21	1-Substituted amino-3-thieno-[3,2-c]pyridinyloxy-2-propanols
JEANLOZ et al.	1961	2-Amino-2-deoxy-D-idose (D-Idosamine) and 2-Amino-2-deoxy-D-talose (D-Talosamine)
JPH08337523A (ja)	1996-12-24	血管新生阻害剤
DE1620147B1 (de)	1972-05-31	Verfahren zur Herstellung von Berbinderivaten
US3856829A (en)	1974-12-24	16{62 -hydrocarbon substituted estrane compounds
Essery et al.	1963	The origin of carbon atoms 4, 5, and 6 of ricinine
US4169201A (en)	1979-09-25	Novel ester precursor intermediates and antipodes for the preparation of 1-(2-tetrahydrofuryl)-5-fluorouracil
KR100344885B1 (ko)	2002-11-30	요실금치료용퀴놀론유도체
NO126320B (fi)	1973-01-22
CA1080218A (en)	1980-06-24	Furanose-o-pyridylcarboxylic acid esters
DK143197B (da)	1981-07-20	Analogifremgangsmaade til fremstilling af 5,7-dihydroxy-tetrahydroisoquinoliner eller farmaceutisk acceptable syreadditionssalte deraf
Shchelchkova et al.	1965	The alkaloids of Stephania glabra
US5776945A (en)	1998-07-07	4A-aryldecahydroisoquinoline compound and medicinal use of the same
Levene et al.	1924	STRUCTURE OF DIACETONE GLUCOSE. SECOND PAPER. 2-METHYL GLUCURONIC ACID AND 4-METHYL GLUCOHEPTONIC LACTONE.
WO2024051666A1 (zh)	2024-03-14	二苄基丁内酯糖苷类化合物、其制备方法和应用
US2393134A (en)	1946-01-15	Dl-tocopherolester
NELSON et al.	1961	Steroidal Hormone Analogs. IX. Bisdehydrodoisynolic Acid Analogs Possessing the 1, 2, 3, 4-Tetrahydrobenz [f] isoquinoline Nucleus1
CA2296478A1 (en)	1999-02-04	Antitumor agents
US3000893A (en)	1961-09-19	Methyl o-piperonyloyl-reserpate