NO125725B - - Google Patents

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Info

Publication number: NO125725B
Authority: NO; Norway
Prior art keywords: acid; salt; hexafluoro; xylyl; copper
Prior art date: 1967-12-20

Application number

NO5011/68A

Other languages

English (en)

Norwegian (no)

Inventor

A Sallmann

R Pfister

Original Assignee

Ciba Geigy Ag

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.)

1967-12-20

Filing date

1968-12-13

Publication date

1972-10-23

1967-12-20 Priority claimed from CH1789067A external-priority patent/CH487842A/de

1968-12-13 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1972-10-23 Publication of NO125725B publication Critical patent/NO125725B/no

Links

150000003839 salts Chemical class 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 14
150000007529 inorganic bases Chemical class 0.000 claims description 4
150000007530 organic bases Chemical class 0.000 claims description 4
238000000034 method Methods 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 2
230000001225 therapeutic effect Effects 0.000 claims description 2
150000001875 compounds Chemical class 0.000 description 8
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
230000008961 swelling Effects 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
230000003110 anti-inflammatory effect Effects 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
229910052802 copper Inorganic materials 0.000 description 4
239000010949 copper Substances 0.000 description 4
210000002683 foot Anatomy 0.000 description 4
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
LPEPZBJOKDYZAD-UHFFFAOYSA-N flufenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 LPEPZBJOKDYZAD-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
206010018691 Granuloma Diseases 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
206010030113 Oedema Diseases 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
230000001741 anti-phlogistic effect Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
239000013078 crystal Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
229960004369 flufenamic acid Drugs 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
-1 potassium carbonate Chemical class 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
XRXMNWGCKISMOH-UHFFFAOYSA-N 2-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
241000700198 Cavia Species 0.000 description 1
239000005749 Copper compound Substances 0.000 description 1
229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
206010015150 Erythema Diseases 0.000 description 1
208000025747 Rheumatic disease Diseases 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
230000002917 arthritic effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000001880 copper compounds Chemical class 0.000 description 1
JMRJRCGXPDVLIZ-UHFFFAOYSA-L copper(1+);carbonate Chemical compound [Cu+].[Cu+].[O-]C([O-])=O JMRJRCGXPDVLIZ-UHFFFAOYSA-L 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
229910000009 copper(II) carbonate Inorganic materials 0.000 description 1
GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
239000011646 cupric carbonate Substances 0.000 description 1
235000019854 cupric carbonate Nutrition 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
231100000321 erythema Toxicity 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
210000000548 hind-foot Anatomy 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000000552 rheumatic effect Effects 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
238000010998 test method Methods 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
238000005303 weighing 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
- A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
- A61K31/245—Amino benzoic acid types, e.g. procaine, novocaine
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04B—KNITTING
- D04B1/00—Weft knitting processes for the production of fabrics or articles not dependent on the use of particular machines; Fabrics or articles defined by such processes
- D04B1/22—Weft knitting processes for the production of fabrics or articles not dependent on the use of particular machines; Fabrics or articles defined by such processes specially adapted for knitting goods of particular configuration
- D04B1/24—Weft knitting processes for the production of fabrics or articles not dependent on the use of particular machines; Fabrics or articles defined by such processes specially adapted for knitting goods of particular configuration wearing apparel
- D04B1/26—Weft knitting processes for the production of fabrics or articles not dependent on the use of particular machines; Fabrics or articles defined by such processes specially adapted for knitting goods of particular configuration wearing apparel stockings

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Emergency Medicine (AREA)
Animal Behavior & Ethology (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO5011/68A 1967-12-20 1968-12-13 NO125725B (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1789067A CH487842A (de)	1966-03-28	1967-12-20	Verfahren zur Herstellung einer neuen, substituierten Anthranilsäure

Publications (1)

Publication Number	Publication Date
NO125725B true NO125725B (fr)	1972-10-23

Family

ID=4428863

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO5011/68A NO125725B (fr)	1967-12-20	1968-12-13

Country Status (13)

Country	Link
US (1)	US3590039A (fr)
AT (1)	AT284093B (fr)
BE (1)	BE725791A (fr)
DE (1)	DE1815804A1 (fr)
DK (1)	DK125988B (fr)
ES (1)	ES361664A1 (fr)
FR (2)	FR1595381A (fr)
GB (1)	GB1253683A (fr)
IE (1)	IE32592B1 (fr)
IL (1)	IL31294A (fr)
NL (1)	NL6817948A (fr)
NO (1)	NO125725B (fr)
SE (1)	SE366297B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1233529B (de) *	1960-11-02	1967-02-02	Max Nebel	Rundgestrickter Strumpf, insbesondere Damenstrumpf
JPS5524116A (en) *	1978-08-08	1980-02-21	Ikeda Mohandou:Kk	Preparation of o-(2, 6-dichloroanilino)-phenylacetic acid
DE3149762A1 (de) *	1981-12-16	1983-06-23	Horst Dr.med. 5000 Köln Kowalsky	Suppositorium
DE3324192A1 (de) *	1983-07-05	1985-01-17	Troponwerke Gmbh & Co Kg	Depot-antiphlogistika

1968
- 1968-12-09 US US782485A patent/US3590039A/en not_active Expired - Lifetime
- 1968-12-13 SE SE17149/68A patent/SE366297B/xx unknown
- 1968-12-13 NL NL6817948A patent/NL6817948A/xx unknown
- 1968-12-13 DK DK612468AA patent/DK125988B/da unknown
- 1968-12-13 NO NO5011/68A patent/NO125725B/no unknown
- 1968-12-19 IE IE1538/68A patent/IE32592B1/xx unknown
- 1968-12-19 GB GB60506/68A patent/GB1253683A/en not_active Expired
- 1968-12-19 ES ES361664A patent/ES361664A1/es not_active Expired
- 1968-12-19 IL IL31294A patent/IL31294A/xx unknown
- 1968-12-19 FR FR1595381D patent/FR1595381A/fr not_active Expired
- 1968-12-19 DE DE19681815804 patent/DE1815804A1/de active Pending
- 1968-12-19 AT AT1236968A patent/AT284093B/de not_active IP Right Cessation
- 1968-12-20 BE BE725791D patent/BE725791A/xx unknown
1969
- 1969-03-17 FR FR183285A patent/FR8261M/fr not_active Expired

Also Published As

Publication number	Publication date
FR1595381A (fr)	1970-06-08
IE32592L (en)	1969-06-20
FR8261M (fr)	1970-10-19
AT284093B (de)	1970-08-25
GB1253683A (en)	1971-11-17
DK125988B (da)	1973-05-28
ES361664A1 (es)	1970-11-01
IL31294A0 (en)	1969-02-27
BE725791A (fr)	1969-06-20
DE1815804A1 (de)	1969-07-24
NL6817948A (fr)	1969-06-24
IE32592B1 (en)	1973-10-03
US3590039A (en)	1971-06-29
IL31294A (en)	1972-08-30
SE366297B (fr)	1974-04-22

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NO170023B (no)	1992-05-25	Analogifremgangsmaate for fremstilling av nye terapeutisk aktive alfa-glucosidaseinhibitorer
US3946029A (en)	1976-03-23	Indole derivatives
JPS6253504B2 (fr)	1987-11-10
IE58097B1 (en)	1993-06-30	7-Carboxymethoxy-furo-(3,4-c)-pyridine derivatives
NO125725B (fr)	1972-10-23
JPH07503015A (ja)	1995-03-30	（２−イミダゾリン−２−イルアミノ）キノキサリン誘導体の使用方法
US4086353A (en)	1978-04-25	Certain azolinylamino (azolidinylimino) indazoles
JPS58154538A (ja)	1983-09-14	アルキルアミノアルコ−ル誘導体、その製造法、並びに該誘導体を有効成分とする新規薬剤
IL32889A (en)	1973-03-30	Pyrido(4,3-b)indole derivatives,their preparation and pharmaceutical compositions containing them
US3255242A (en)	1966-06-07	(alpha-alkylideneacyl)naphthyloxy monocarboxylic acids
NO150160B (no)	1984-05-21	Analogifremgangsmaate for fremstilling av den terapeutisk aktive forbindelse 1,3-dihydro-3(3`,4`,5`-trimetoksy-styryl)-6-metyl-7-hydroksy-furo(3,4-c)pyridin
DE3335472A1 (de)	1985-04-11	5h-(1)benzopyrano-(2,3,-d)pyrimidin-derivate, verfahren zu deren herstellung sowie deren verwendung bei der bekaempfung von gastralen und duodenalen schleimhautlaesionen
Krantz Jr et al.	1947	Sodium theophylline glycinate
US4012394A (en)	1977-03-15	Indole derivatives
US3534142A (en)	1970-10-13	Methods of treating tapeworm infections with naphthamidines
US3420839A (en)	1969-01-07	Aminomethyl pyrazolone derivatives of nicotinamide
US3996222A (en)	1976-12-07	Piperazine derivatives
US3637679A (en)	1972-01-25	Quaternary phenothiazine sulfamate
SK68599A3 (en)	2000-06-12	Guanidinylamino heterocycle compounds useful as alpha-2 adrenoceptor agonists
JPS6026381B2 (ja)	1985-06-24	４−ヒドロキシベンゾフエノン類の塩基性エ−テルおよびその製法
US3847920A (en)	1974-11-12	3-substituted pyrimido(4,5-b)indoles
SU1042614A3 (ru)	1983-09-15	Способ получени 2-бензил-3-(3-диметиламинопропилтио)-2 @ -индазола
US2566038A (en)	1951-08-28	Water-soluble sulfonamides
NO743260L (fr)	1975-04-07
US3324173A (en)	1967-06-06	(2-methylenealkanoyl)benzoic acids