NO133894B - - Google Patents

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Info

Publication number: NO133894B
Authority: NO; Norway
Prior art keywords: acid; chloro; nicotinic acid; hydroxy; compound
Prior art date: 1970-11-23

Application number

NO4263/71A

Other languages

English (en)

Norwegian (no)

Other versions

NO133894C (fr

Inventor

Alden G Beaman

Oscar N Miller

Original Assignee

Hoffmann La Roche

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.)

1970-11-23

Filing date

1971-11-18

Publication date

1976-04-05

1971-11-18 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1976-04-05 Publication of NO133894B publication Critical patent/NO133894B/no

1976-07-14 Publication of NO133894C publication Critical patent/NO133894C/no

Links

HLXITPCEBVXBDJ-UHFFFAOYSA-N 6-chloro-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)N=C1O HLXITPCEBVXBDJ-UHFFFAOYSA-N 0.000 claims description 12
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 8
AJPKQSSFYHPYMH-UHFFFAOYSA-N 2,6-dichloropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)N=C1Cl AJPKQSSFYHPYMH-UHFFFAOYSA-N 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
238000000034 method Methods 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
150000001875 compounds Chemical class 0.000 description 14
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
239000002585 base Substances 0.000 description 8
235000012000 cholesterol Nutrition 0.000 description 6
239000002253 acid Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
150000002632 lipids Chemical class 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
229930182558 Sterol Natural products 0.000 description 4
235000014113 dietary fatty acids Nutrition 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
150000004665 fatty acids Chemical class 0.000 description 4
150000003432 sterols Chemical class 0.000 description 4
235000003702 sterols Nutrition 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
201000001320 Atherosclerosis Diseases 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000012259 ether extract Substances 0.000 description 3
230000000055 hyoplipidemic effect Effects 0.000 description 3
238000005342 ion exchange Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
210000004185 liver Anatomy 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
229960003512 nicotinic acid Drugs 0.000 description 3
235000001968 nicotinic acid Nutrition 0.000 description 3
239000011664 nicotinic acid Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
-1 sodium hydroxide Chemical class 0.000 description 3
239000007787 solid Substances 0.000 description 3
IHLBCGVADAYUDV-UHFFFAOYSA-N 4-chloro-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC(=O)C1=C(Cl)C=CNC1=O IHLBCGVADAYUDV-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
239000013543 active substance Substances 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
230000004136 fatty acid synthesis Effects 0.000 description 2
210000000056 organ Anatomy 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
239000002243 precursor Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
230000002285 radioactive effect Effects 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000007017 scission Effects 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
KJTLQQUUPVSXIM-ZCFIWIBFSA-N (R)-mevalonic acid Chemical class OCC[C@](O)(C)CC(O)=O KJTLQQUUPVSXIM-ZCFIWIBFSA-N 0.000 description 1
BSCFFOOWFVZSSK-UHFFFAOYSA-N 2-chloro-6-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC(=O)C=1C=CC(=O)NC=1Cl BSCFFOOWFVZSSK-UHFFFAOYSA-N 0.000 description 1
MASVCBBIUQRUKL-UHFFFAOYSA-N POPOP Chemical compound C=1N=C(C=2C=CC(=CC=2)C=2OC(=CN=2)C=2C=CC=CC=2)OC=1C1=CC=CC=C1 MASVCBBIUQRUKL-UHFFFAOYSA-N 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000003708 ampul Substances 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000007850 degeneration Effects 0.000 description 1
230000037213 diet Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000010339 dilation Effects 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
RFKMCNOHBTXSMU-UHFFFAOYSA-N methoxyflurane Chemical compound COC(F)(F)C(Cl)Cl RFKMCNOHBTXSMU-UHFFFAOYSA-N 0.000 description 1
229960002455 methoxyflurane Drugs 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229940014662 pantothenate Drugs 0.000 description 1
235000019161 pantothenic acid Nutrition 0.000 description 1
239000011713 pantothenic acid Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
238000003825 pressing Methods 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
238000003345 scintillation counting Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000001360 synchronised effect Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
210000003462 vein Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)

NO714263A 1970-11-23 1971-11-18 NO133894C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US9213770A	1970-11-23	1970-11-23
US9229670A	1970-11-23	1970-11-23

Publications (2)

Publication Number	Publication Date
NO133894B true NO133894B (fr)	1976-04-05
NO133894C NO133894C (fr)	1976-07-14

Family

ID=26785310

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO714263A NO133894C (fr)	1970-11-23	1971-11-18

Country Status (12)

Country	Link
AR (1)	AR192334A1 (fr)
BE (1)	BE775641A (fr)
CH (1)	CH558798A (fr)
DE (1)	DE2157334A1 (fr)
ES (1)	ES397243A1 (fr)
FR (1)	FR2115357B1 (fr)
GB (1)	GB1317239A (fr)
HU (1)	HU163713B (fr)
IE (1)	IE36016B1 (fr)
IL (1)	IL38089A (fr)
NL (1)	NL7115903A (fr)
NO (1)	NO133894C (fr)

1971
- 1971-11-03 CH CH1612471A patent/CH558798A/xx not_active IP Right Cessation
- 1971-11-08 IL IL38089A patent/IL38089A/xx unknown
- 1971-11-18 DE DE19712157334 patent/DE2157334A1/de active Pending
- 1971-11-18 NL NL7115903A patent/NL7115903A/xx unknown
- 1971-11-18 NO NO714263A patent/NO133894C/no unknown
- 1971-11-19 IE IE1468/71A patent/IE36016B1/xx unknown
- 1971-11-22 ES ES397243A patent/ES397243A1/es not_active Expired
- 1971-11-22 BE BE775641A patent/BE775641A/fr unknown
- 1971-11-23 AR AR239196A patent/AR192334A1/es active
- 1971-11-23 FR FR7141921A patent/FR2115357B1/fr not_active Expired
- 1971-11-23 GB GB5436671A patent/GB1317239A/en not_active Expired
- 1971-11-23 HU HUHO1435A patent/HU163713B/hu unknown

Also Published As

Publication number	Publication date
AU3556471A (en)	1973-05-17
IL38089A (en)	1975-08-31
GB1317239A (en)	1973-05-16
CH558798A (de)	1975-02-14
DE2157334A1 (de)	1972-05-31
FR2115357B1 (fr)	1974-10-18
IL38089A0 (en)	1972-01-27
ES397243A1 (es)	1975-04-16
HU163713B (fr)	1973-10-27
AR192334A1 (es)	1973-02-14
NO133894C (fr)	1976-07-14
FR2115357A1 (fr)	1972-07-07
IE36016L (en)	1972-05-23
IE36016B1 (en)	1976-07-21
NL7115903A (fr)	1972-05-25
BE775641A (fr)	1972-05-23

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Hikino et al.	1980	Antiinflammatory principle of Ephedra herbs
US3622587A (en)	1971-11-23	Certain 3-pyridylmethyl-2-(p-chloro phenoxy)-2-methyl propionate-n-oxides and derivatives thereof
US3849561A (en)	1974-11-19	Anti-peptic ulcer substance from corydalis tubers
Parke et al.	1963	THE FATE OF TRITIUM‐LABELLED β‐GLYCYRRHETIC ACID IN THE RAT
DE2323746C2 (de)	1987-04-30	Estersalze der 2,5-Dihydroxybenzolsulfonsäure, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
US11560358B2 (en)	2023-01-24	Resveratrol-piperazine co-crystals
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PT88924B (pt)	1993-01-29	Processo para a preparacao de derivados de ginkgolidos
NO133894B (fr)	1976-04-05
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JPH06122623A (ja)	1994-05-06	抗腫瘍剤
US3567832A (en)	1971-03-02	New hypotensive and oddian spasmolytic pharmaceutical methods employing various hydroxy coumarines
EP0564648B1 (fr)	2000-05-03	Compose d'aconitine et agent analgesique/anti-inflammatoire
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US4247466A (en)	1981-01-27	Lactone metabolites of 3-(4-biphenylylcarbonyl)propionic acid
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US3005818A (en)	1961-10-24	1-phenyl-2, 3-dimethyl-4-morpholino methyl pyrazolone-(5) compounds
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Klohs et al.	1954	Alkaloids of Veratrum eschscholizii Gray. II. 1 The Ester Alkaloids
DE2005255C3 (de)	1981-05-14	Verwendung von Ca-5-butylpicolinat und/oder Ca-5-pentylpicolinat zur Herstellung eines blutdrucksenkenden Arzneimittels
JPS6222714A (ja)	1987-01-30	脂質代謝促進剤
US3155579A (en)	1964-11-03	Therapeutic composition for the treatment of disturbances of the water metabolism characterized by an insufficient elmination of water
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