DK145820B - ANALOGY PROCEDURE FOR PREPARING D-2- (6-METHOXY-2-NAPHTHYL) PROPANAL - Google Patents
ANALOGY PROCEDURE FOR PREPARING D-2- (6-METHOXY-2-NAPHTHYL) PROPANAL Download PDFInfo
- Publication number
- DK145820B DK145820B DK186170AA DK186170A DK145820B DK 145820 B DK145820 B DK 145820B DK 186170A A DK186170A A DK 186170AA DK 186170 A DK186170 A DK 186170A DK 145820 B DK145820 B DK 145820B
- Authority
- DK
- Denmark
- Prior art keywords
- naphthyl
- methoxy
- propanal
- preparing
- analogy procedure
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
(19) DANMARK(19) DENMARK
|p (12) FREML/EGGELSESSKRIFT ου 145820 B| p (12) FOREIGN / ANNOUNCEMENT OF 145820 B
DIREKTORATET FOR PATENT- OG VAREMÆRKEVÆSENETDIRECTORATE OF THE PATENT AND TRADEMARKET SYSTEM
(21) Ansøgning nr. 18β1 /ΥΟ (51) |nt.CI.3 C 07 C 47/277 (22) Indleveringsdag 1 ^ 1970 (24) Løbedag 14. apr. 1970 (41) Aim. tilgængelig 10. apr. 1971 (44) Fremlagt 1 ^ · niar. 1985 (86) International ansøgning nr. - (86) International indleveringsdag - (85) Videreførelsesdag - (62) Stamansøgning nr. -(21) Application No. 18β1 / ΥΟ (51) | nt.CI.3 C 07 C 47/277 (22) Filing day 1 ^ 1970 (24) Running day 14 Apr. 1970 (41) Aim. available Apr 10 1971 (44) Presented 1 ^ niar. 1985 (86) International Application No. - (86) International Filing Day - (85) Continuation Day - (62) Master Application No. -
(30) Prioritet 9* okt. 1969* 865216, US(30) Priority 9 * Oct. 1969 * 865216, US
(71) Ansøger SYNTEX CORPORATION, Panama, PA.(71) Applicant SYNTEX CORPORATION, Panama, PA.
(72) Opfinder John Hans Pried, US: Ian Thomas Harrison, US.(72) Inventor John Hans Pried, US: Ian Thomas Harrison, US.
(74) Fuldmægtig Firmaet Chas. Hude.(74) Associate Company Chas. Hude.
(54) Analogifremgangsmåde til fremstil= ling af d-2- (6-methoxy-2-naph.th.yl) -propanal.(54) Analogous procedure for the preparation of d-2- (6-methoxy-2-naphthyl) propanal.
Den foreliggende opfindelse angår en analogifremgangsmåde til fremstilling af d-2-(6-methoxy-2-naphthyl)-propanal.The present invention relates to an analogous process for the preparation of d-2- (6-methoxy-2-naphthyl) propanal.
Det er kendt, at d,1-2-(6-methoxy-2-naphthyl)-propanal har antiinflammatorisk virkning, jvf. dansk patentansøgning nr. 3638/69.It is known that d, 1-2- (6-methoxy-2-naphthyl) propanal has anti-inflammatory effect, cf. Danish Patent Application No. 3638/69.
ffi Det har nu vist sig, at d-2-(6-methoxy-2-naphthyl) -propanal ^ har en stærkere antiinflammatorisk virkning end den racemiskeIt has now been found that d-2- (6-methoxy-2-naphthyl) -propanol has a stronger anti-inflammatory effect than the racemic
CvJCVJ
00 forbindelse, hvilket blev konstateret ved prøven med car- ^ rageenininduceret poteinflammation hos rotter, der udføres -*3' t— som følger: * Q Der anvendes hunrotter, som vejer 80-90 g. Forsøgsmaterialer ne indgives til tidspunktet 0 ved tvangsfodring i 1 ml vandig bærer. Efter 1 time injiceres 0,05 ml af en 1%'ig 2 145820 opløsning (i 0,9% NaCl) af carrageenin i den højre bagpote. Denne injektion forårsager inflammation af poten. Rotterne dræbes 3 timer efter injektionen, og begge bagpoter fjernes og vejes separat, og man beregner den procen-5 tiske forøgelse af potestørrelsen som følger: Vægt af højre bagpote - Vægt af venstre bagpote χ Vægt af venstre bagpote00, which was found in the test with carrageenin-induced protein inflammation in rats performed - * 3 't - as follows: * Q Female rats weighing 80-90 g are used. 1 ml aqueous carrier. After 1 hour, 0.05 ml of a 1% solution (in 0.9% NaCl) of carrageenin is injected into the right hind paw. This injection causes inflammation of the paw. The rats are killed 3 hours after injection, and both hind legs are removed and weighed separately, and the percent increase in paw size is calculated as follows: Weight of right hind paw - Weight of left hind paw χ Weight of left hind paw
Resultaterne af disse forsøg er vist i følgende tabel:The results of these experiments are shown in the following table:
Forbindelse Oral antiinflammatorisk virkning d,1-2-(6-methoxy-2- naphthyl)-propanal 1 d-2- (6-methoxy-2- naphthyl)-propanal 1 3Compound Oral anti-inflammatory action d, 1-2- (6-methoxy-2-naphthyl) -propanal 1 d-2- (6-methoxy-2-naphthyl) -propanal 1 3
Den ifølge opfindelsen fremstillede forbindelse er med andre 10 ord mindst 3 gange så aktiv som den racemiske forbindelse.In other words, the compound of the invention is at least 3 times as active as the racemic compound.
d-2-(6-methoxy-2-naphthyl)-propanal udviser foruden anti-inflammatorisk også analgetisk og antipyretisk virkning. Forbindelsen kan derfor anvendes til behandling og mildnelse af betændelse, smerte og pyrexia hos pattedyr, 15 Forbindelsen er særlig nyttig til behandling af betændelse såsom betændelsestilstande i muskelskeletsysternet, skelets led og andre væv. Forbindelsen er derfor nyttig til behandling af tilstande, der karakteriseres ved betændelse, såsom rheumatisme, kvæstelse, sønderrivelse, arthritis, knog-20 lefrakturer, posttraumatiske tilstande og gigt. I de tilfælde , hvori de ovennævnte tilstande indbefatter smerte og pyrexia sammen med betændelse, er forbindelsen nyttig til mildnelse af disse tilstande og af betændelsen.In addition to anti-inflammatory, d-2- (6-methoxy-2-naphthyl) propanal also exhibits analgesic and antipyretic action. The compound can therefore be used to treat and alleviate inflammation, pain and pyrexia in mammals. The compound is particularly useful for treating inflammation such as inflammatory conditions in the musculoskeletal system, skeletal joints and other tissues. The compound is therefore useful for treating conditions characterized by inflammation such as rheumatism, injury, tearing, arthritis, bone fractures, post-traumatic conditions, and arthritis. In cases where the above conditions include pain and pyrexia along with inflammation, the compound is useful in alleviating these conditions and of the inflammation.
145820 3145820 3
Den foretrukne administrationsmåde er oral administration, som anvender en bekvem daglig dosering, der kan indstilles i overensstemmelse med graden af ydelsen. I almindelighed anvendes en daglig dosis fra 0,1 mg til 60 mg aktiv for-5 bindelse pr. kg legemsvægt af pattedyret. De fleste til stande reagerer overfor behandling, der omfatter et doseringsniveau af størrelsesordenen 0,5 til 5 mg.The preferred mode of administration is oral administration which uses a convenient daily dosage which can be adjusted according to the degree of performance. Generally, a daily dose of 0.1 mg to 60 mg of active compound is used per day. kg body weight of the mammal. Most patients respond to treatment comprising a dosage level of the order of 0.5 to 5 mg.
Fremgangsmåden ifølge opfindelsen er ejendommelig ved, at a) 1-2-(6-methoxy-2-naphthyl)-1-propanol oxideres, eller 10 b) d-2-(6-methoxy-2-naphthyl)-propionsyre reduceres.The process of the invention is characterized in that a) 1-2- (6-methoxy-2-naphthyl) -1-propanol is oxidized, or b) d-2- (6-methoxy-2-naphthyl) -propionic acid is reduced.
Opfindelsen illustreres nærmere af følgende eksempler.The invention is further illustrated by the following examples.
Eksempel 1.Example 1.
En opløsning af 23 g d-2-(6-methoxy-2-naphthyl)-propionsyre (kendt fra sydafrikansk patent nr. 67/7597) i 100 ml benzol 15 og 20 ml thionylchlorid opvarmes under tilbagesvaling i 2 timer. Reaktionsblandingen inddampes så i vakuum til dannelse af det tilsvarende syrechlorid. En opløsning af remanensen i 300 ml tetrahydrofuran afkøles til -80°C og behandles med 47 g lithiumaluminiumtritertiær-butoxyhydrid 20 (2 molære ækvivalenter). Efter omrøring af reaktionsbland ingen ved denne temperatur i 1 time får blandingen lov at opvarmes til stuetemperatur og hældes i vand.A solution of 23 g of d-2- (6-methoxy-2-naphthyl) propionic acid (known from South African Patent No. 67/7597) in 100 ml of benzene 15 and 20 ml of thionyl chloride is heated under reflux for 2 hours. The reaction mixture is then evaporated in vacuo to give the corresponding acid chloride. A solution of the residue in 300 ml of tetrahydrofuran is cooled to -80 ° C and treated with 47 g of lithium aluminum tritertiary-butoxyhydride 20 (2 molar equivalents). After stirring the reaction mixture at this temperature for 1 hour, the mixture is allowed to warm to room temperature and poured into water.
Blandingen ekstraheres så med benzol, og den organiske fase inddampes i vakuum til dannelse af d-2-(6-methoxy-2-25 naphthyl)-propanal, der omkrystalliseres af en blanding af dichlormethan og hexan.The mixture is then extracted with benzene and the organic phase is evaporated in vacuo to give d-2- (6-methoxy-2-25 naphthyl) propanal, which is recrystallized from a mixture of dichloromethane and hexane.
Eksempel 2.Example 2.
En opløsning af 58Q mg 1-2-(6-methoxy-2-naphthyl)-l-pro= panol (kendt fra dansk patent nr. 141.165) i 25 ml di=A solution of 58Q mg of 1-2- (6-methoxy-2-naphthyl) -1-propanol (known from Danish Patent No. 141,165) in 25 ml of di =
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86521669A | 1969-10-09 | 1969-10-09 | |
| US86521669 | 1969-10-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK145820B true DK145820B (en) | 1983-03-14 |
| DK145820C DK145820C (en) | 1983-09-05 |
Family
ID=25344966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK186170A DK145820C (en) | 1969-10-09 | 1970-04-14 | ANALOGY PROCEDURE FOR PREPARING D-2- (6-METHOXY-2-NAPHTHYL) PROPANAL |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS54908B1 (en) |
| BE (1) | BE747925A (en) |
| BR (1) | BR6915468D0 (en) |
| CA (1) | CA921492A (en) |
| CH (2) | CH546724A (en) |
| DE (2) | DE2065420C2 (en) |
| DK (1) | DK145820C (en) |
| ES (2) | ES383496A1 (en) |
| FI (1) | FI50521C (en) |
| FR (1) | FR2068541B1 (en) |
| GB (1) | GB1297306A (en) |
| IL (1) | IL33947A (en) |
| NL (1) | NL7004198A (en) |
| NO (1) | NO131593C (en) |
| SE (1) | SE362066B (en) |
| ZA (1) | ZA701177B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK156642B (en) * | 1973-09-11 | 1989-09-18 | Beecham Group Ltd | ANALOGY PROCEDURE FOR THE PREPARATION OF NAPTHALEND DERIVATIVES |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4912248A (en) * | 1987-05-18 | 1990-03-27 | The Procter & Gamble Company | Novel anti-inflammatory agents, pharmaceutical compositions and methods for reducing inflammation |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3562336A (en) * | 1968-07-24 | 1971-02-09 | Syntex Corp | Synthesis of naphthalene derivatives |
| US3637767A (en) * | 1968-07-30 | 1972-01-25 | Syntex Corp | 2-(6'-methoxynaphth-2'-yl)propylene oxide and 5'-halo derivatives |
-
1969
- 1969-12-19 BR BR215468/69A patent/BR6915468D0/en unknown
-
1970
- 1970-02-23 ZA ZA701177A patent/ZA701177B/en unknown
- 1970-02-23 CA CA075524A patent/CA921492A/en not_active Expired
- 1970-02-23 IL IL33947A patent/IL33947A/en unknown
- 1970-03-05 FI FI700605A patent/FI50521C/en active
- 1970-03-10 GB GB1297306D patent/GB1297306A/en not_active Expired
- 1970-03-20 NO NO1043/70A patent/NO131593C/no unknown
- 1970-03-24 JP JP2479570A patent/JPS54908B1/ja active Pending
- 1970-03-24 NL NL7004198A patent/NL7004198A/xx unknown
- 1970-03-25 BE BE747925D patent/BE747925A/en not_active IP Right Cessation
- 1970-04-14 DK DK186170A patent/DK145820C/en not_active IP Right Cessation
- 1970-04-20 FR FR707014295A patent/FR2068541B1/fr not_active Expired
- 1970-08-10 SE SE10932/70A patent/SE362066B/xx unknown
- 1970-08-27 CH CH149873A patent/CH546724A/en not_active IP Right Cessation
- 1970-08-27 CH CH1286570A patent/CH549547A/en not_active IP Right Cessation
- 1970-08-31 DE DE2065420A patent/DE2065420C2/en not_active Expired
- 1970-08-31 DE DE2043048A patent/DE2043048C3/en not_active Expired
- 1970-09-09 ES ES70383496A patent/ES383496A1/en not_active Expired
-
1973
- 1973-04-02 ES ES413265A patent/ES413265A1/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK156642B (en) * | 1973-09-11 | 1989-09-18 | Beecham Group Ltd | ANALOGY PROCEDURE FOR THE PREPARATION OF NAPTHALEND DERIVATIVES |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2043048A1 (en) | 1971-04-22 |
| DE2065420C2 (en) | 1982-07-22 |
| FI50521C (en) | 1976-04-12 |
| IL33947A (en) | 1973-06-29 |
| FR2068541A1 (en) | 1971-08-27 |
| JPS54908B1 (en) | 1979-01-18 |
| SE362066B (en) | 1973-11-26 |
| DE2065420A1 (en) | 1973-07-05 |
| DE2043048C3 (en) | 1974-06-27 |
| NL7004198A (en) | 1971-04-14 |
| CH546724A (en) | 1974-03-15 |
| NO131593B (en) | 1975-03-17 |
| DE2043048B2 (en) | 1973-11-15 |
| CA921492A (en) | 1973-02-20 |
| ES413265A1 (en) | 1976-06-16 |
| NO131593C (en) | 1975-07-02 |
| GB1297306A (en) | 1972-11-22 |
| FI50521B (en) | 1975-12-31 |
| CH549547A (en) | 1974-05-31 |
| DK145820C (en) | 1983-09-05 |
| ZA701177B (en) | 1971-09-29 |
| ES383496A1 (en) | 1973-07-01 |
| FR2068541B1 (en) | 1973-04-06 |
| BR6915468D0 (en) | 1973-03-13 |
| BE747925A (en) | 1970-08-31 |
| IL33947A0 (en) | 1970-04-20 |
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| Date | Code | Title | Description |
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| PUP | Patent expired |