FI62050C - Foerfarande foer framstaellning av guajacol p-isobutyl-hydratropat - Google Patents
Foerfarande foer framstaellning av guajacol p-isobutyl-hydratropat Download PDFInfo
- Publication number
- FI62050C FI62050C FI771833A FI771833A FI62050C FI 62050 C FI62050 C FI 62050C FI 771833 A FI771833 A FI 771833A FI 771833 A FI771833 A FI 771833A FI 62050 C FI62050 C FI 62050C
- Authority
- FI
- Finland
- Prior art keywords
- isobutyl
- hydratropat
- reference frame
- release plate
- frame release
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/10—Expectorants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
RJSF^l [ft] (11)KUULUTUSjULKAISU 620 5 0
4GTa lJ '' UTLÄCGNINOSSKRIFT O^USU
c(45) Patentti myönnetty 10 11 1902 ΛΛ*2Ι Patent meddelat V(51) Kv.lk?/lnt.CI.3 C 0? C 69/612 SUOMI —FINLAND (21) Pu*nttlh*ktfW*-rtt#nt*n«öknlnI 771833 (22) Hekemlipilvt — Ans6knln(»d«t 10.06.77 (FI) (23) Alkvptlvl — Glkljheudaj 10.06.77 (41) Tullut |ulklMkal — Bllvlt off*ntll| 10.01.78
Patantti- ja raklitarihallitut /44) Niht*vtkjip«non fa kuuL|uik«i»un pvm. — 30.07.82
Patant· och ragi«ter*tyralsan AnsMcan utlagd och utl.tkrtften publkerad (32)(33)(31) Pyrdatty «cuotkwn —ftajird priori»·» 09 · 07 · 76
Italia-Italien(IT) 2517^ A/76 (71) Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.p.A., via Amelia, 70, Roma, Italia-Italien(lT) (72) Leandro Baiocchi, Roma, Bruno Silvestrini, Roma, Italia-Italien(lT) (jh) Leitzinger Oy (5*0 Guajakoli p-isobutyyli-hydratropaatin valmistusmenetelmä - Förfarande för framställning av guajacol p-isobutyl-hydratropat
Oheisen keksinnön kohteena on menetelmä, jolla valmistetaan uutta, kaavan (I) mukaista tuotetta, jonka nimi on guajakolin p-isobutyyli-hydratropaatti och3
-CO
(i)
Keksinnön mukaiselle menetelmälle on tunnusomaista, että p-isobutyyli-hydratropoyylikloridi kondensoidaan guajakolin kanssa happokatalyyt-tien läsnäollessa.
Yhdisteillä (I) on analgeettinen, anti-inflanmatorinen, antipyreetti-nen, antiseptinen ja ysköksiä poistava aktiivisuus laboratorioeläi-millä.
Alhaisen toksisuutensa ja laajakirjoisen farmakologisen käytettävyytensä ansiosta sitä voitaneen käyttää päivittäisinä annoksina 0,5 - 2,5 g hoidettaessa hengitystiehyeen tulehdustiloja (akuutti ja krooli 2 62050 ninen bronkiitti jne.) ihmisillä. Oheisen keksinnön mukaisesti yhdiste (I) valmistetaan lähtemällä p-isobutyyli-hydratropoyyli-kloridista ja guajakolista happokatalyytin (HC1, H2S04, p-tolueeni-sulfonihappo, jne.) läsnäollessa. Yhdistettä on yritetty valmistaa eri tavoin tavanomaisimmin keinoin, mutta niiden ei ole havaittu olevan kovinkaan mielenkiintoisia käytännön kannalta ja alhaisten sääntöjensä (p-isobutyyli-hydratropoyylikloridin vaikutus natrium-guajakoliin) tai liian monien vaiheiden (p-isobutyyli-hydratrooppi-happoesterin transesteröinti tai yhdistettä (I) vastaavan hydroksi-johdannaisen metylointi) vuoksi.
Seuraava esimerkki havainnollistaa keksintöä.
Seosta, joka sisältää p-isobutyyli-hydratropoyylikloridia (21,5 g), guajakolia (8,4 g) ja pisaran väkevää rikkihappoa, sekoitetaan 24 tuntia huoneen lämpötilassa ja sen jälkeen edelleen 30 minuuttia vesihauteessa. Seoksen jäähdyttämisen jälkeen se uutetaan eetterillä ja pestään natriumbikarbonaattiliuoksella ja sen jälkeen vedellä. Liuottimen poistamisen jälkeen saatu jäännös tislataan, kiehumispisteestä 190°C/0,5 mm/Hg. Saanto 21 g.
Tuote kiteytyy seisotettaessa, sp. 35 - 36°C NMR (CDCl^, TMS sisäisenä standardina)-spektri:
Multipletti välillä 6,70 - 7,506(8H) (aromaattiset protonit)
Kvartetti, keskus 3,956 (1H) Ar-CH-CH^
Singletti, 3,606(3H)-0CH3
Dupletti, keskus 2,466 (2H) Ar-CH^-CH
Dupletti, keskus 1, 576 (3H) CH3-CH CH
Multipletti välillä 1,5 - 2,26(1H)-CH^-CHL ^ CH^ " CH3
Dupletti, keskus 0,906 (6H) CH
CH3^ -1 IR-spektri (kalvo)yC=0 = 1760 cm
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2517476 | 1976-07-09 | ||
| IT25174/76A IT1064751B (it) | 1976-07-09 | 1976-07-09 | P. isobutil idratropato di guaiacolo |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI771833A FI771833A (fi) | 1978-01-10 |
| FI62050B FI62050B (fi) | 1982-07-30 |
| FI62050C true FI62050C (fi) | 1982-11-10 |
Family
ID=11215909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI771833A FI62050C (fi) | 1976-07-09 | 1977-06-10 | Foerfarande foer framstaellning av guajacol p-isobutyl-hydratropat |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4134989A (fi) |
| JP (1) | JPS588379B2 (fi) |
| AT (1) | AT348508B (fi) |
| BE (1) | BE861107A (fi) |
| BG (1) | BG60795B2 (fi) |
| CA (1) | CA1093578A (fi) |
| DE (1) | DE2726435C3 (fi) |
| DK (1) | DK310777A (fi) |
| FI (1) | FI62050C (fi) |
| FR (1) | FR2357526A1 (fi) |
| GB (1) | GB1538636A (fi) |
| HU (1) | HU174532B (fi) |
| IE (1) | IE45010B1 (fi) |
| IL (1) | IL52320A (fi) |
| IT (1) | IT1064751B (fi) |
| NL (1) | NL174824C (fi) |
| PL (1) | PL106527B1 (fi) |
| PT (1) | PT66772B (fi) |
| SE (1) | SE418287B (fi) |
| SU (1) | SU665795A3 (fi) |
| YU (1) | YU162577A (fi) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1190727B (it) * | 1982-03-10 | 1988-02-24 | Ausonia Farma Srl | Composto ad attivita' analgesica,antiinfiammatoria e mucoregolatrice procedimento per la sua preparazione e relative composizioni farmaceutiche |
| JPS60141841U (ja) * | 1984-02-29 | 1985-09-19 | 富田 忠雄 | ハ−ブマツト |
| JPS6131260U (ja) * | 1984-07-31 | 1986-02-25 | ロフテ−株式会社 | 香枕 |
| JPS6177868U (fi) * | 1984-10-27 | 1986-05-24 | ||
| JPS6388168U (fi) * | 1986-11-29 | 1988-06-08 | ||
| US5648358A (en) * | 1996-03-05 | 1997-07-15 | Mitra; Sekhar | Compositions and methods for treating respiratory disorders |
| JP3040364U (ja) * | 1996-07-23 | 1997-08-19 | 清秀 中川 | 芳香含有物質の詰め替え可能な枕 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3452079A (en) * | 1964-06-15 | 1969-06-24 | Merck & Co Inc | Acetic acid type compounds |
| IT1045533B (it) * | 1974-05-15 | 1980-05-10 | Acraf | P.isobutil idratropato di 4 acetamido fenile e procedimento per la sua prefarazione |
-
1976
- 1976-07-09 IT IT25174/76A patent/IT1064751B/it active Protection Beyond IP Right Term
-
1977
- 1977-06-10 FI FI771833A patent/FI62050C/fi not_active IP Right Cessation
- 1977-06-11 DE DE2726435A patent/DE2726435C3/de not_active Expired
- 1977-06-13 NL NLAANVRAGE7706508,A patent/NL174824C/xx not_active IP Right Cessation
- 1977-06-15 IL IL52320A patent/IL52320A/xx unknown
- 1977-06-17 JP JP52072722A patent/JPS588379B2/ja not_active Expired
- 1977-06-24 US US05/809,833 patent/US4134989A/en not_active Expired - Lifetime
- 1977-06-28 FR FR7719856A patent/FR2357526A1/fr active Granted
- 1977-06-30 YU YU01625/77A patent/YU162577A/xx unknown
- 1977-07-04 IE IE1376/77A patent/IE45010B1/en unknown
- 1977-07-05 SE SE7707811A patent/SE418287B/xx unknown
- 1977-07-06 PT PT66772A patent/PT66772B/pt unknown
- 1977-07-07 GB GB28554/77A patent/GB1538636A/en not_active Expired
- 1977-07-08 SU SU772500953A patent/SU665795A3/ru active
- 1977-07-08 HU HU77AI272A patent/HU174532B/hu unknown
- 1977-07-08 DK DK310777A patent/DK310777A/da not_active Application Discontinuation
- 1977-07-08 CA CA282,344A patent/CA1093578A/en not_active Expired
- 1977-07-08 PL PL1977199471A patent/PL106527B1/pl not_active IP Right Cessation
- 1977-07-08 AT AT493577A patent/AT348508B/de not_active IP Right Cessation
- 1977-11-23 BE BE182858A patent/BE861107A/xx not_active IP Right Cessation
-
1994
- 1994-02-24 BG BG98556A patent/BG60795B2/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE45010B1 (en) | 1982-06-02 |
| YU162577A (en) | 1982-06-30 |
| BE861107A (fr) | 1978-03-16 |
| NL174824B (nl) | 1984-03-16 |
| NL7706508A (nl) | 1978-01-11 |
| US4134989A (en) | 1979-01-16 |
| PT66772B (en) | 1978-12-15 |
| PL199471A1 (pl) | 1978-08-14 |
| AT348508B (de) | 1979-02-26 |
| IT1064751B (it) | 1985-02-25 |
| PL106527B1 (pl) | 1979-12-31 |
| FR2357526B1 (fi) | 1982-09-03 |
| GB1538636A (en) | 1979-01-24 |
| BG60795B2 (bg) | 1996-03-29 |
| DE2726435C3 (de) | 1981-08-20 |
| FI62050B (fi) | 1982-07-30 |
| ATA493577A (de) | 1978-07-15 |
| DE2726435A1 (de) | 1978-01-12 |
| IE45010L (en) | 1978-01-09 |
| JPS5325536A (en) | 1978-03-09 |
| HU174532B (hu) | 1980-02-28 |
| FR2357526A1 (fr) | 1978-02-03 |
| SU665795A3 (ru) | 1979-05-30 |
| NL174824C (nl) | 1984-08-16 |
| JPS588379B2 (ja) | 1983-02-15 |
| PT66772A (en) | 1977-08-01 |
| SE7707811L (sv) | 1978-01-10 |
| CA1093578A (en) | 1981-01-13 |
| IL52320A0 (en) | 1977-08-31 |
| DK310777A (da) | 1978-01-10 |
| SE418287B (sv) | 1981-05-18 |
| DE2726435B2 (de) | 1980-10-09 |
| FI771833A (fi) | 1978-01-10 |
| IL52320A (en) | 1980-02-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: AZIENDE CHIMICHE RIUNITE ANGELINI |