FI56377C - FOERFARANDE FOER FRAMSTAELLNING AV 7-BENZOYLINDOLIN-2-ONER SOM FOERHINDRAR INFLAMMATION FOERORSAKAD AV LUNGSAECKSIRRITATION - Google Patents
FOERFARANDE FOER FRAMSTAELLNING AV 7-BENZOYLINDOLIN-2-ONER SOM FOERHINDRAR INFLAMMATION FOERORSAKAD AV LUNGSAECKSIRRITATION Download PDFInfo
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- FI56377C FI56377C FI1452/73A FI145273A FI56377C FI 56377 C FI56377 C FI 56377C FI 1452/73 A FI1452/73 A FI 1452/73A FI 145273 A FI145273 A FI 145273A FI 56377 C FI56377 C FI 56377C
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- benzoylindolin
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- inflammation
- lungsaecksirritation
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/24—Disazo or polyazo compounds
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- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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- 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]
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- 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
- A61P9/08—Vasodilators for multiple indications
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
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Description
1- -^-""» ΓηΊ ηη KUULUTUSJULKAISU c £ O 1 1 JSTa lBJ 11) UTLAGGNI NGSSKRIFT 5bJ// C (45) Patentti myönnetty 10 01 1930 Patent meddelat ' (51) Kv.lk.*/lnt.CI.* C 0? D 209/32 SUOMI —FINLAND (21) Ptt*nttlhak«mi* —P«t«K«n»aknlng 1^52/73 (22) Hikamiipllvl — Ansttknlnpdag 07.05· 73 (23) Alkupilvt —Glltlghctsdag 07.05.73 (41) Tullut Julkiseksi — Blivlt offtntllg 2.8 11 73 totmttU )« rakistarihallitus (44) Nlhav|kilpMOn „ touMulw<un1- - ^ - "" »ΓηΊ ηη ANNOUNCEMENT c £ O 1 1 JSTa lBJ 11) UTLAGGNI NGSSKRIFT 5bJ // C (45) Patent granted 10 01 1930 Patent meddelat '(51) Kv.lk. * / Lnt.CI. * C 0? D 209/32 FINLAND —FINLAND (21) Ptt * nttlhak «mi * —P« t «K« n »aknlng 1 ^ 52/73 (22) Hikamiipllvl - Ansttknlnpdag 07.05 · 73 (23) Alkupilvt —Glltlghctsdag 07.05.73 ( 41) Became Public - Blivlt offtntllg 2.8 11 73 totmttU) «Rakistarihallitus (44) Nlhav | kilpMOn„ touMulw <un
Patent· och registerstyrelsan # Amekm uthgd och utUkrtfUn public·»* 28.09.79 (32)(33)(31) Pietty atuolkws —Begird priority 17.05.72 USA(US) 25^28¾ (71) A.H. Robins Company, Incorporated, lh07 Cummings Drive, Richmond,Patent · och registerstyrelsan # Amekm uthgd och utUkrtfUn public · »* 28.09.79 (32) (33) (31) Pietty atuolkws —Begird priority 17.05.72 USA (US) 25 ^ 28¾ (71) A.H. Robins Company, Incorporated, lh07 Cummings Drive, Richmond,
Virginia 23220, USA(US) (72) William John Welstead, Jr., Richmond, Virginia, Henry Wayne Moran,Virginia 23220, USA (72) William John Welstead, Jr., Richmond, Virginia, Henry Wayne Moran,
Richmond, Virginia, USA(US) (7*0 Berggren Oy Ab (54) Menetelmä keuhkopussiärsytyksen aiheuttamaa tulehdusta ehkäisevien 7-bentsoyyli-indoliini-2-onien valmi stand.seksi - Förfarande för framställning av 7-benzoylindolin-2-oner som förhindrar inflammation förorsakad av lungsäcksirritation Tämä keksintö kohdistuu menetelmään keuhkopussiärsytyksen aiheuttamaa tulehdusta ehkäisevien 7“bentsoyyli-indoliini-2-onien valmistamiseksi.Richmond, Virginia, USA (US) (7 * 0 Berggren Oy Ab (54) Method for the preparation of 7-benzoylindolin-2-ones for the prevention of inflammation caused by pleural irritation - For the preparation of 7-benzoylindolin-2-ones with the same value This invention relates to a process for the preparation of 7 'benzoylindolin-2-ones for the prevention of inflammation caused by pleural irritation.
Keksintö kohdistuu erityisesti menetelmään sellaisten 7-bentso-yyli-indoliini-2-onien valmistamiseksi, joilla on kaava:In particular, the invention relates to a process for the preparation of 7-benzoyl-indolin-2-ones having the formula:
_ R_ R
o . To. T
ηρ kaava Iηρ formula I
0 = C I0 = C I
HB
Rl-f*SR f * S
jossa R on vety tai alhainen alkyyli, ja R1 on vety tai halogeeni.wherein R is hydrogen or lower alkyl, and R 1 is hydrogen or halogen.
Kaavan I yhdisteet ehkäisevät keuhkopussiärsytyksen aiheuttamaa tulehdusta. Aktiviteetti havainnollistettiin käyttäen L.F. Sancilio'n muunnosta Evans'in sinilevä-keuhkopussipurkaustestistä, J. Pharmacol. Exp. Ther. 168, 199“204 (1969).The compounds of formula I prevent inflammation caused by pleural irritation. Activity was illustrated using L.F. A modification of Sancilio from the Evans cyanobacterial pleural effusion test, J. Pharmacol. Exp. Ther. 168, 199-204 (1969).
2 56377 7-Bentsoyyli-indoliini-2-onien valmistaminen tapahtuu keksinnön mukaan syklisoimalla etyyli“2-asetamid6-3-bentsoyylifenyyli-asetaatti (II) tai 2-asetamido-3-bentsoyylifenyyli-etikkahappo (Ha) 7-bentsoyyli-indoliini-2-onin (I) aikaansaamiseksi.The preparation of 7-benzoylindolin-2-ones according to the invention takes place by cyclization of ethyl 2-acetamide-6-benzoylphenylacetate (II) or 2-acetamido-3-benzoylphenylacetic acid (IIa) 7-benzoylindolin-2-one. -one (I).
Reaktiokaava on seuraava:The reaction formula is as follows:
Λ p /V / RΛ p / V / R
CHRCOOR^ . Λί-( I h Hl —NHCOCH ^ —--> C = 0 Q = o 0- ’ , ö-'1CHRCOOR ^. Λί- (I h Hl —NHCOCH ^ —--> C = 0 Q = o 0- ', ö-'1
(II) R -C-HL(II) R -C-HL
25 (I)25 (I)
(Ha) R2 = H(Ha) R2 = H
Etyyli-2-asetamido-3~bentsoyylifenyyliasetaatti (II) ja 2-asetamido-3-bentsoyylifenyylietikkahapot (Ha) valmistetaan seu-raavalla reaktiosarjalla lähtien l-aminoindoliini-2-oneista (III). Jälkimmäiset yhdisteet valmistetaan Baumgarten'in ym. selostamalla menetelmällä, J. Am. Chem. Soc. 82, 3977-3982 (i960).Ethyl 2-acetamido-3-benzoylphenylacetate (II) and 2-acetamido-3-benzoylphenylacetic acids (IIa) are prepared by the following series of reactions starting from 1-aminoindolin-2-ones (III). The latter compounds are prepared by the method described by Baumgarten et al., J. Am. Chem. Soc. 82, 3977–3982 (i960).
Λ (Λτ—TRΛ (Λτ — TR
NH„ ANH „A
Rl__(T>-ch2—0—'=H3 (III) (IV) (V) ,_ n C„HcOH,HClR1 __ (T> -ch2-0 - '= H3 (III) (IV) (V), _ n C „HcOH, HCl
^—rCT ; 1} 0H~ ^ ,/TT^ -RCT; 1} 0H ~ ^, / TT
. 2) H+ f |1 f. 2) H + f | 1 f
I ^h3 N>vCHI ^ h3 N> vCH
chr mio Ichr mio I
C.iR HC.iR H
C00H (VII) COOC2H5 (VI) H+ ,0-, H+,03 ψ y I 3 I 56377 s^'^'CmcooH ^\/chrcooc2h5 Y^NHC0CH3 kAfflCOCH, c = o X . 0 5C 10 H (VII) COOC 2 H 5 (VI) H +, O-, H +, O 3 I y I 3 I 56377 s 0 5
1 V1 V
*0 "‘O* 0 "‘ O
(Ila) (II) l-aminoindoliini-2-oni (III) saatetaan reagoimaan fenyyli-asetonin (IV) kanssa etanolissa, joka sisältää katalyyttisen määrän etikkahappoa, jolloin saadaan l-(oc-metyylifenetylideeni-imino)indo-liini-2-oni (V). Jälkimmäinen yhdiste kuumennetaan alhaisessa alkanolissa, edullisesti etanolissa, joka on kyllästetty kloori-vedyllä, jolloin saadaan etyyii-oc-(2-metyyli-3-f’enyyli-indoli-7-yyli)asetaatti (VI), jota käsitellään otsonilla etikkahapossa, jolioin saadaan etyyli-2-asetamido-3-bentsoyylifenyyliasetaatti. Vaihtoehtoinen lähtöaine, 2-asetamido-3-bentsoyylifenyylietikkahappoa (Ila), saadaan hydrolysoimalla emäksisesti esteri (VI) hapoksi (VII), jota käsitellään otsonilla etikkahapossa, jolloin saadaan 2-asetamido- 3-bentsoyylifenyylietikkahappoa (Ha) .(IIa) (II) 1-Aminoindolin-2-one (III) is reacted with phenylacetone (IV) in ethanol containing a catalytic amount of acetic acid to give 1- (α-methylphenethylideneamino) indoline-2- oni (V). The latter compound is heated in a low alkanol, preferably ethanol saturated with hydrogen chloride to give ethyl α- (2-methyl-3-phenylindol-7-yl) acetate (VI), which is treated with ozone in acetic acid, whereby ethyl 2-acetamido-3-benzoylphenyl acetate is obtained. An alternative starting material, 2-acetamido-3-benzoylphenylacetic acid (IIa), is obtained by basic hydrolysis of ester (VI) to acid (VII) which is treated with ozone in acetic acid to give 2-acetamido-3-benzoylphenylacetic acid (IIa).
Lähtöaineiden valmistus:Preparation of starting materials:
Valmistus 1Preparation 1
Etyyli-2-asetamido-3~bentsoyylifenyyliasetaattiEthyl-2-acetamido-3 ~ bentsoyylifenyyliasetaatti
Liuosta, jossa oli 5 g (0,017 moolia) etyyli-oc-(2~metyyli-3~ fenyyli-indoli-7-yyli) asetaattia ja 75 ml etikkahappoa, käsiteltiin otsonilla 25 minuuttia. Otsonoinnin jälkeen etikkahappoliuos laimennettiin vedellä ja uutettiin eetterillä. Eetteriuutteet pestiin vedellä, 5 %’· sella natriumkarbonaatilla, kuivattiin (magnesiumsulfaatti) ja väkevöitiin. Uudelleenkiteyttäminen isopropanolista antoi 2,6 g (47 %) tuotetta, joka suli 133-134°C:ssa.A solution of 5 g (0.017 mol) of ethyl α- (2-methyl-3-phenylindol-7-yl) acetate and 75 ml of acetic acid was treated with ozone for 25 minutes. After ozonation, the acetic acid solution was diluted with water and extracted with ether. The ether extracts were washed with water, 5% sodium carbonate, dried (magnesium sulfate) and concentrated. Recrystallization from isopropanol gave 2.6 g (47%) of product, melting at 133-134 ° C.
Analyysi: laskettu yhdisteelle C^H^NO^: C 70,14; N 5*89; N 4,30 saatu : c 69,95; H 5,99; N 4,12Analysis: Calculated for C 18 H 18 NO 3: C, 70.14; N 5 * 89; N 4.30 Found: c 69.95; H 5.99; N 4.12
Valmistus 2 2-asetamido-3~bentsoyylifenyylietikkahappoPreparation 2 2-Acetamido-3-benzoylphenylacetic acid
Liuosta, jossa oli 2 g <*-(2-metyyli-3-fenyyli-indoli-7-yyli)-etikkahappoa 60 ml:ssa etikkahappoa, käsiteltiin otsonilla 15 minuuttia. Reaktiosesota käsiteltiin 10 ml:lla vettä ja annettiin haihtua yön yli. Jäännös (1,7 g) uudelleenkiteytettiin isopropanolista, saanto 1,6 g (71 %), sp. 188-190°C.A solution of 2 g of <* - (2-methyl-3-phenylindol-7-yl) -acetic acid in 60 ml of acetic acid was treated with ozone for 15 minutes. The reaction mixture was treated with 10 ml of water and allowed to evaporate overnight. The residue (1.7 g) was recrystallized from isopropanol, yield 1.6 g (71%), m.p. 188-190 ° C.
Analyysi: laskettu yhdisteelle C-^H^NO^: C 68,68; H 5,08; N 4,71 saatu : C 68,33; H 5,11; N 4,58 4 56377Analysis: Calculated for C 18 H 18 N 2 O 2: C, 68.68; H 5.08; N 4.71 Found: C 68.33; H 5.11; N 4.58 4 56377
Keksinnön mukainen menetelmä:Method according to the invention:
Esimerkki 1Example 1
7-bentsoyyli-indoliini-2-oni Menetelmä A7-Benzoyl-indolin-2-one Method A
Keitettiin palautusjäähdyttäen tunnin ajan seosta, jossa oli 2,5 g (0,0077 moolia) etyyli-2-asetamido-3-bentsoyylifenyyliasetaat-tia 50 ml:ssa 3-n suolahappoa. Reaktioseos suodatettiin ja suodate kaadettiin jään ja veden seokseen. Sakka otettiin talteen ja uudel-leenkiteytettiin asetonista, saanto 1 g (55 %), sp. 154°C.A mixture of 2.5 g (0.0077 mol) of ethyl 2-acetamido-3-benzoylphenylacetate in 50 ml of 3N hydrochloric acid was refluxed for 1 hour. The reaction mixture was filtered and the filtrate was poured into a mixture of ice and water. The precipitate was collected and recrystallized from acetone, yield 1 g (55%), m.p. 154 ° C.
Analyysi: laskettu yhdisteelle C^H^NOg! C 75,9**; H 4,67; N 5,90 saatu : c 75,84; H 4,76; N 5,78.Analysis: Calculated for C C 75.9 **; H 4.67; N 5.90 Found: c 75.84; H 4.76; N 5.78.
Menetelmä BMethod B
Keitettiin palautusjäähdyttäen 3 tuntia liuosta, jossa oli 1,3 g (0,0044 moolia) 2-asetamido-3-bentsoyylifenyylietikkahappoa 15 ml:ssa 3-n suolahappoa ja 15 ml:ssa etikkahappoa. Jäähtynyt liuos kaadettiin jääveteen ja saostunut 7-bentsoyyli-indoliini-2-oni otettiin talteen ja kuivattiin.A solution of 1.3 g (0.0044 mol) of 2-acetamido-3-benzoylphenylacetic acid in 15 ml of 3-hydrochloric acid and 15 ml of acetic acid was refluxed for 3 hours. The cooled solution was poured into ice water and the precipitated 7-benzoylindolin-2-one was collected and dried.
Esimerkki 2Example 2
Muita 7-bentsoyyli-indoliini-2-oneja, so. 7-(4-klooribentso-yyli)-indoliini-2-onia ja 7-bentsoyyli-3-metyyli-indoliini-2-onia valmistettiin esimerkin 1 tavalla syklisoimalla vastaava etyyli-2-asetamido-3-bentsoyylifenyyliasetaattia tai 2-asetamido-3-bentsoyylifenyylietikkahappoa. Saatu 7-(4-klooribentsoyyli)indoliini-2-oni suli l860C:ssa.Other 7-benzoylindolin-2-ones, i. 7- (4-Chlorobenzoyl) -indolin-2-one and 7-benzoyl-3-methyl-indolin-2-one were prepared as in Example 1 by cyclization of the corresponding ethyl 2-acetamido-3-benzoylphenylacetate or 2-acetamido-3-one. -bentsoyylifenyylietikkahappoa. The resulting 7- (4-chlorobenzoyl) indolin-2-one melted at 18 ° C.
Analyysi: laskettu yhdisteelle C^H^Cl-NO,,: C 66,31; H 3,71; N 5,16 saatu : C 65,97; H 3,56; N 5,11.Analysis: Calculated for C 18 H 18 Cl 2 NO 2: C, 66.31; H 3.71; N 5.16 Found: C 65.97; H 3.56; N 5.11.
Saatu 7-bentsoyyli-3-metyyli-indoliini-2-oni suli 125-127°C:ssa. Analyysi: laskettu yhdisteelle ci6Hi3N02: C 76,43; H 5,22; N 5,57 saatu : C 76,38; H 5,22; N 5,52.The obtained 7-benzoyl-3-methylindolin-2-one melted at 125-127 ° C. Analysis: Calculated for C 16 H 13 NO 2: C, 76.43; H 5.22; N 5.57 Found: C 76.38; H 5.22; N 5.52.
Keksinnön mukaisella menetelmällä valmistettuja yhdisteitä voidaan käyttää aktiivisina ainesosina lisättynä sopivaan kantajaan, esim. farmaseuttiseen kantajaan. Sopivia farmaseuttisia kantajia, jotka ovat käyttökelpoisia tällaisia seoksia muodostettaessa, ovat tärkkelys, gelatiini, glukoosi, magnesiumkarbonaatti, laktoosi, mallas ja sentapaiset. Sopivia nestemäisiä farmaseuttisia kantajia ovat etyylialkoholi, propyleeniglykoli, glyseriini, glukoosi-siirappi ja sentapaiset.The compounds prepared by the process of the invention may be used as active ingredients in association with a suitable carrier, e.g. a pharmaceutical carrier. Suitable pharmaceutical carriers useful in forming such compositions include starch, gelatin, glucose, magnesium carbonate, lactose, malt, and the like. Suitable liquid pharmaceutical carriers include ethyl alcohol, propylene glycol, glycerin, glucose syrup and the like.
5 563775 56377
Alla annetaan esimerkkejä edellä mainituista seoksista.Examples of the above mixtures are given below.
1. Kapselit1. Capsules
Valmistettiin 50 ja 100 mg aktiivista ainesosaa kapselia kohti sisältäviä kapseleita.Capsules containing 50 and 100 mg of active ingredient per capsule were prepared.
Tyypillinen seos kapselointia varten Kapselia kohti, mg Aktiivinen ainesosa 50,0Typical mixture for encapsulation Per capsule, mg Active ingredient 50.0
Laktoosi 251,7 Tärkkelys 129*0Lactose 251.7 Starch 129 * 0
Magnesiumstearaatti 4,3Magnesium stearate 4.3
Yhteensä 435,0 mgA total of 435.0 mg
Muut kapseliseokset sisältävät edullisesti suurempia annoksia aktiivista ainesosaa ja ovat:Other capsule compositions preferably contain higher doses of active ingredient and are:
Ainesosat 100 mg kapselia kohtiIngredients 100 mg per capsule
Aktiivinen ainesosa 100,0Active ingredient 100.0
Laktoosi 231,5 Tärkkelys 99,2Lactose 231.5 Starch 99.2
Magnesiumstearaatti 4,3Magnesium stearate 4.3
Yhteensä 435,0A total of 435.0
Kussakin tapauksessa sekoitettiin valittu aktiivinen ainesosa tasaisesti laktoosin, tärkkelyksen ja magnesiumstearaatin kanssa ja seos kapseloitiin. 1 2 3In each case, the selected active ingredient was mixed uniformly with lactose, starch and magnesium stearate and the mixture was encapsulated. 1 2 3
Tabletittablets
Seuraavassa annetaan tyypillinen seos tablettia varten, joka sisälsi 50,0 mg aktiivista ainesosaa tablettia kohti. Seosta voidaan käyttää muille aktiivisen ainesosan väkevyyksille säätämällä dikalsiumfosfaatin painoa.The following is a typical mixture for a tablet containing 50.0 mg of active ingredient per tablet. The mixture can be used for other active ingredient concentrations by adjusting the weight of the dicalcium phosphate.
Tablettia kohti, mg 1. Aktiivinen ainesosa 50,0 2. Milo-tärkkelys 20,0 2Per tablet, mg 1. Active ingredient 50.0 2. Milo starch 20.0 2
Maissitärkkelys (tahna) 38,0 3Maize starch (paste) 38.0 3
Laktoosi 90,0 5- Kalsiumstearaatti 2,0Lactose 90.0 5- Calcium stearate 2.0
Yhteensä 200,0 mgA total of 200.0 mg
Claims (2)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US25428472A | 1972-05-17 | 1972-05-17 | |
US25428472 | 1972-05-17 |
Publications (2)
Publication Number | Publication Date |
---|---|
FI56377B FI56377B (en) | 1979-09-28 |
FI56377C true FI56377C (en) | 1980-01-10 |
Family
ID=22963675
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Application Number | Title | Priority Date | Filing Date |
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FI1452/73A FI56377C (en) | 1972-05-17 | 1973-05-07 | FOERFARANDE FOER FRAMSTAELLNING AV 7-BENZOYLINDOLIN-2-ONER SOM FOERHINDRAR INFLAMMATION FOERORSAKAD AV LUNGSAECKSIRRITATION |
Country Status (17)
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JP (2) | JPS5139222B2 (en) |
AT (1) | AT323731B (en) |
BE (2) | BE799612A (en) |
CA (1) | CA1000715A (en) |
CH (1) | CH577469A5 (en) |
DE (2) | DE943075C (en) |
DK (1) | DK139677B (en) |
ES (1) | ES414802A1 (en) |
FI (1) | FI56377C (en) |
FR (1) | FR2184933B1 (en) |
GB (1) | GB1432577A (en) |
IE (1) | IE37641B1 (en) |
IL (1) | IL42216A (en) |
NL (2) | NL183187C (en) |
PH (1) | PH9815A (en) |
SE (1) | SE393980B (en) |
ZA (1) | ZA733151B (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS5371842U (en) * | 1976-11-17 | 1978-06-15 | ||
US4221716A (en) * | 1979-02-16 | 1980-09-09 | A. H. Robins Company, Inc. | Intermediate and process for the preparation of 7-acylindolin-2-ones |
DE3300522A1 (en) * | 1982-01-21 | 1983-07-28 | Sandoz-Patent-GmbH, 7850 Lörrach | 3,3-DIALKYL AND 3,3-ALKYLENE INDOLINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL PREPARATIONS CONTAINING THE SAME |
JPH0349563Y2 (en) * | 1985-08-31 | 1991-10-23 |
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CH232507A (en) * | 1941-02-18 | 1944-05-31 | Chem Ind Basel | Process for the preparation of a disazo dye. |
-
0
- NL NL90149D patent/NL90149C/xx active
- BE BE524637D patent/BE524637A/xx unknown
-
1953
- 1953-11-25 DE DEC8502A patent/DE943075C/en not_active Expired
-
1973
- 1973-05-07 FI FI1452/73A patent/FI56377C/en active
- 1973-05-08 IL IL42216A patent/IL42216A/en unknown
- 1973-05-09 ZA ZA733151A patent/ZA733151B/en unknown
- 1973-05-11 PH PH14608A patent/PH9815A/en unknown
- 1973-05-11 DK DK263073AA patent/DK139677B/en unknown
- 1973-05-15 CH CH689973A patent/CH577469A5/xx not_active IP Right Cessation
- 1973-05-15 SE SE7306853A patent/SE393980B/en unknown
- 1973-05-16 AT AT429973A patent/AT323731B/en not_active IP Right Cessation
- 1973-05-16 DE DE2324767A patent/DE2324767C2/en not_active Expired
- 1973-05-16 CA CA171,512A patent/CA1000715A/en not_active Expired
- 1973-05-16 NL NLAANVRAGE7306832,A patent/NL183187C/en not_active IP Right Cessation
- 1973-05-16 BE BE131181A patent/BE799612A/en not_active IP Right Cessation
- 1973-05-16 GB GB2337473A patent/GB1432577A/en not_active Expired
- 1973-05-16 FR FR7317755A patent/FR2184933B1/fr not_active Expired
- 1973-05-16 ES ES414802A patent/ES414802A1/en not_active Expired
- 1973-05-17 JP JP48054204A patent/JPS5139222B2/ja not_active Expired
- 1973-05-17 IE IE785/73A patent/IE37641B1/en unknown
-
1976
- 1976-05-13 JP JP51054786A patent/JPS5910660B2/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
BE524637A (en) | |
IE37641L (en) | 1973-11-17 |
CH577469A5 (en) | 1976-07-15 |
NL90149C (en) | |
AT323731B (en) | 1975-07-25 |
FR2184933A1 (en) | 1973-12-28 |
NL183187B (en) | 1988-03-16 |
JPS4941366A (en) | 1974-04-18 |
JPS5910660B2 (en) | 1984-03-10 |
ES414802A1 (en) | 1976-02-01 |
JPS5139222B2 (en) | 1976-10-26 |
DE2324767A1 (en) | 1973-11-29 |
JPS5217466A (en) | 1977-02-09 |
AU5584773A (en) | 1974-11-21 |
DE2324767C2 (en) | 1985-07-25 |
SE393980B (en) | 1977-05-31 |
GB1432577A (en) | 1976-04-22 |
CA1000715A (en) | 1976-11-30 |
NL7306832A (en) | 1973-11-20 |
IL42216A (en) | 1976-08-31 |
PH9815A (en) | 1976-03-26 |
DK139677B (en) | 1979-03-26 |
IE37641B1 (en) | 1977-09-14 |
NL183187C (en) | 1988-08-16 |
BE799612A (en) | 1973-09-17 |
DE943075C (en) | 1956-05-09 |
IL42216A0 (en) | 1973-07-30 |
DK139677C (en) | 1979-09-10 |
ZA733151B (en) | 1974-04-24 |
FR2184933B1 (en) | 1976-05-14 |
FI56377B (en) | 1979-09-28 |
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