DD149803A5 - Verfahren zur herstellung von 4-(n-hexadecylamino)benzoesaeure - Google Patents

Verfahren zur herstellung von 4-(n-hexadecylamino)benzoesaeure Download PDF

Info

Publication number: DD149803A5
Authority: DD; German Democratic Republic
Prior art keywords: hexadecylamino; benzoic acid; acid; acceptable salts; physiologically acceptable
Prior art date: 1979-03-09

Application number

DD80219530A

Other languages

German (de)

English (en)

Inventor

Branko Jenko

Natasa Hafner-Milac

Joza Habjan

Anton Prosen

Igor Langof

Original Assignee

Lek Tovarna Farmacevtskih

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.)

1979-03-09

Filing date

1980-03-07

Publication date

1981-07-29

1980-03-07 Application filed by Lek Tovarna Farmacevtskih filed Critical Lek Tovarna Farmacevtskih

1981-07-29 Publication of DD149803A5 publication Critical patent/DD149803A5/de

Links

WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title description 7
-1 N-HEXADECYLAMINO Chemical class 0.000 title description 2
238000004519 manufacturing process Methods 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 11
QXWKHSSBFQDQPR-UHFFFAOYSA-N 4-(hexadecylamino)benzoic acid Chemical compound CCCCCCCCCCCCCCCCNC1=CC=C(C(O)=O)C=C1 QXWKHSSBFQDQPR-UHFFFAOYSA-N 0.000 claims abstract description 10
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims abstract description 9
HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 claims abstract description 8
238000010992 reflux Methods 0.000 claims abstract description 8
239000003054 catalyst Substances 0.000 claims abstract description 7
150000003839 salts Chemical class 0.000 claims abstract description 6
229960004050 aminobenzoic acid Drugs 0.000 claims abstract description 5
238000002360 preparation method Methods 0.000 claims abstract description 5
150000004714 phosphonium salts Chemical class 0.000 claims abstract description 3
239000002904 solvent Substances 0.000 claims abstract description 3
239000002253 acid Substances 0.000 claims abstract 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 7
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
239000008280 blood Substances 0.000 abstract description 2
210000004369 blood Anatomy 0.000 abstract description 2
239000003814 drug Substances 0.000 abstract description 2
150000003904 phospholipids Chemical class 0.000 abstract description 2
230000035484 reaction time Effects 0.000 abstract description 2
150000003626 triacylglycerols Chemical class 0.000 abstract description 2
150000003863 ammonium salts Chemical class 0.000 abstract 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 7
239000000047 product Substances 0.000 description 5
ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 3
239000005711 Benzoic acid Substances 0.000 description 3
230000029936 alkylation Effects 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
235000010233 benzoic acid Nutrition 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
JSKCHHZATDKBBP-UHFFFAOYSA-N 2-(hexadecylamino)benzoic acid Chemical compound CCCCCCCCCCCCCCCCNC1=CC=CC=C1C(O)=O JSKCHHZATDKBBP-UHFFFAOYSA-N 0.000 description 1
206010003210 Arteriosclerosis Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
206010061926 Purulence Diseases 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
208000011775 arteriosclerosis disease Diseases 0.000 description 1
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
229960000541 cetyl alcohol Drugs 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
230000000055 hyoplipidemic effect Effects 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
NNENFOSYDBTCBO-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC NNENFOSYDBTCBO-UHFFFAOYSA-M 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Heart & Thoracic Surgery (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Urology & Nephrology (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Compositions Of Macromolecular Compounds (AREA)

DD80219530A 1979-03-09 1980-03-07 Verfahren zur herstellung von 4-(n-hexadecylamino)benzoesaeure DD149803A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
YU00579/79A YU57979A (en)	1979-03-09	1979-03-09	Process for preparing 4-9n-hexadecylamino0-benzoic acid

Publications (1)

Publication Number	Publication Date
DD149803A5 true DD149803A5 (de)	1981-07-29

Family

ID=25550533

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80219530A DD149803A5 (de)	1979-03-09	1980-03-07	Verfahren zur herstellung von 4-(n-hexadecylamino)benzoesaeure

Country Status (9)

Country	Link
US (1)	US4304929A (cs)
AT (1)	ATA104980A (cs)
CS (1)	CS214703B2 (cs)
DD (1)	DD149803A5 (cs)
ES (1)	ES489078A0 (cs)
HU (1)	HU183073B (cs)
PL (1)	PL222469A1 (cs)
SU (1)	SU869557A3 (cs)
YU (1)	YU57979A (cs)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3868416A (en) *	1973-10-01	1975-02-25	American Cyanamid Co	Hypolipidemic 4-(monoalkylamino)benzoic acid derivatives
US4154756A (en) *	1977-12-15	1979-05-15	American Cyanamid Company	2-Substituted-4'-(monoalkylamino)-acetophenones

1979
- 1979-03-09 YU YU00579/79A patent/YU57979A/xx unknown
1980
- 1980-02-26 AT AT0104980A patent/ATA104980A/de not_active IP Right Cessation
- 1980-02-29 ES ES80489078A patent/ES489078A0/es active Granted
- 1980-03-04 CS CS801497A patent/CS214703B2/cs unknown
- 1980-03-05 PL PL22246980A patent/PL222469A1/xx unknown
- 1980-03-06 SU SU802891749A patent/SU869557A3/ru active
- 1980-03-07 HU HU80537A patent/HU183073B/hu unknown
- 1980-03-07 US US06/128,208 patent/US4304929A/en not_active Expired - Lifetime
- 1980-03-07 DD DD80219530A patent/DD149803A5/de unknown

Also Published As

Publication number	Publication date
ES8100659A1 (es)	1980-12-01
HU183073B (en)	1984-04-28
CS214703B2 (en)	1982-05-28
ATA104980A (de)	1981-11-15
YU57979A (en)	1982-10-31
PL222469A1 (cs)	1981-01-02
SU869557A3 (ru)	1981-09-30
US4304929A (en)	1981-12-08
ES489078A0 (es)	1980-12-01

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