FI89707B - Foerfarande foer framstaellning av en ny aminderivata - Google Patents
Foerfarande foer framstaellning av en ny aminderivata Download PDFInfo
- Publication number
- FI89707B FI89707B FI870342A FI870342A FI89707B FI 89707 B FI89707 B FI 89707B FI 870342 A FI870342 A FI 870342A FI 870342 A FI870342 A FI 870342A FI 89707 B FI89707 B FI 89707B
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- FI
- Finland
- Prior art keywords
- compound
- formula
- naphthylmethyl
- benzylamine
- propyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/31—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system formed by at least three rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/28—Halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
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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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
89707
MENETELMÄ UUDEN AMIINIJOHDANNAISEN VALMISTAMISEKSI -FÖRFARANDE FÖR FRAMSTÄLLNING AV EN NY AMINDERIVATA
, Esillä oleva keksintö koskee menetelmää uuden, 5 terapeuttisesti käyttökelpoisen amiinijohdannaisen valmistamiseksi.
Patenttijulkaisussa EP 164 697 on kuvattu esillä olevaan keksintöön nähden tekniikan tasoa kuvaavia amiinijohdannaisia, jotka omaavat fungisidista 10 vaikutusta mutta joiden rakenne poikkeaa oleellisesti esillä olevasta keksinnön mukaisen yhdisteen rakenteesta. Patenttihakemusjulkaisussa FI 771185 on kuvattu menetelmä eräiden indoliyhdisteiden pelkistämiseksi stereospesifisesti. Ko. indoliyhdisteet voivat omata 15 farmaseuttista aktiivisuutta, antifungisidista vaikutusta ei näille ole kuitenkaan ehdotettu. Patenttihakemus julkaisussa FI 834400 on puolestaan kuvattu yhdisteitä, jotka säätelevät lipoksigenaasin muodostumista ja joita voidaan käyttää anti-inflammatorisinä ja an-20 tiallergisina aineina.
Esillä oleva keksintö tuo esiin uuden yhdisteen, N-metyyli-N-(1-na ftyy1imetyy1i)-4-(2-fenyy1i-2-propyyli)bentsyyliamiinin, jonka on yllättäen todettu omaavan voimakasta antifungisidista aktiivisuutta ai-25 kaisempiin tunnettuihin, rakenteeltaan samankaltaisiin ··· yhdisteisiin nähden.
Esillä oleva keksintö tuo edelleen esiin menetelmän uuden yhdisteen, N-metyyli-N-(1-naftyylime-tyyli)-4-(2-fenyyli-2-propyyli)bentsyyliamiinin val-30 mistamiseksi vapaan emäksen muodossa tai happoaddi-tiosuolan muodossa, jolloin menetelmän mukaisesti: : i) yhdisteen, jolla on kaava VI, V : ch3
: 35 ,--N- CH2 - OR
% o5 89707 2 jossa R on alempi alkyyli, annetaan reagoida yhdisteen kanssa, jolla on kaava VII, CH3
Me -fV» Γ~\ 5 W7 , w
' '— VII
ch3 jossa Me on metalliekvivalentti, tai ii) yhdisteen, jolla on kaava Via, 10 CH3 ch3 RO-CHo -N - CH2 —C -714 CH3 15 jossa R tarkoittaa samaa kuin edellä, annetaan reagoida yhdisteen kanssa, jolla on kaava Vila,
Me 00 : jossa Me tarkoittaa samaa kuin edellä, ja saatu keksinnön mukainen yhdiste otetaan talteen vapaassa muodossa tai happoadditiosuolan muodossa.
25 Keksinnön mukaiset menetelmävaiheet voidaan suorittaa organometalliyhdlsteiden reaktiohin liittyvillä tunnetuilla tekniikoilla. Menetelmävaiheet suoritetaan edullisesti inertissä liuottimessa, esim. eetterissä, läm-pötilavälillä -20°C - +50°C.
30 Lopputuote voidaan eristää ja puhdistaa ta vanomaiseen tapaan. Keksinnön mukaisen yhdisteen vapaa emäsmuoto voidaan muuttaa suolamuodoiksi ja päinvastoin. Sopivia happoadditiosuoloja ovat hydrokloridi, vetyfumaraatti tai naftaliini-l,5-disulfonaatti.
35 Kaavojen VI ja Via mukaiset lähtöaineet voi daan valmistaa antamalla vastaavan amiinin reagoida formaldehydin ja kaavan RÖH mukaisen alemman alkoholin 8 9 7 07 3 kanssa.
Keksinnön mukainen yhdiste omaa edullisia kemoterapeuttisia ominaisuuksia ja erityisesti se omaa paikallisesti tai oraalisesti annettuna antimykoottista 5 aktiivisuutta,' ja siten sitä voidaan käyttää farmaseuttisena aineena, erityisesti antimykoottina. Tämä aktiivisuus voidaan osoittaa erilaisten sieniperheiden ja -lajien, esim. Trichophyton spp., Aspergillus spp., Microsporum spp., Sporothrix schenckii ja Candida spp., 10 avulla sekä in vitro-laimennuskokeilla konsentraatioil-la 0.003-50 pg/ml ja marsujen in vivo ihomykoosikokeel-la ja intravaginaali-intrauterinäärisillä tai hajape-säkkeisillä infektioilla. Ihomykoosikokeessa testiaine sekoitetaan polyetyleeniglykoliin ja seosta hierotaan 15 päivittäin 7 päivän ajan infektoituneen ihon pinnalle. Antimykoottinen aktiivisuus voidaan havaita kon-sentraatiolla 0.1-2%. Oraalinen aktiivisuus voidaan osoittaa in vivo marsun trikofytoosikokeessa annoksilla 2-70 mg/kg ruumiin paino.
20 Indikoitu päiväannos on esim. välillä 70-2000 mg annettuna sopivasti jaettuina annoksina 2-4 kertaa päivässä tai kontrolloidusti vapautuvassa muodossa; esim. oraaliseen antoon sopivat annosmuodot sisältävät . . 17.5-1000 mg aktiivista aineosaa.
25 Keksinnön mukaista yhdistettä voidaan käyttää vapaan emäksen muodossa tai farmaseuttisesti hyväksyttävän happoadditiosuolan muodossa. Tavallisesti nämä muodot omaavat saman aktiivisuusasteen kuin vapaan * -· emäksen muodot. Esimerkkeinä tällaisista happoadditio- 30 suoloista voidaan mainita hydrokloridi, vetyfumaraatti ja naftaliini-l,5-disulfonaatti.
: Yhdiste voidaan sekoittaa tavanomaisten far maseuttisesti hyväksyttävien laimennusaineiden ja kantajien kanssa ja, valinnaisesti, muiden täyteaineiden 35 kanssa, ja se voidaan antaa oraalisesti, paikallisesti, i.v. tai parenteraalisesti esim. tablettien, kapselei-:·. den, voiteiden, tinktuuroiden tai injektoitavien vai- 89707 4 misteiden muodossa.
Keksintö liittyy myös tällaisiin ainekokoomuk- siin.
Keksinnön mukaista yhdistettä voidaan siten 5 käyttää sienien aiheuttamien infektioiden ja tautien hoitoon, jolloin vapaassa muodossa tai sen farmaseuttisesti hyväksyttävän suolan muodossa olevaa keksinnön mukaista yhdistettä annetaan vaikuttava määrä tällaista hoitoa tarvitsevalle kohteelle.
10 Keksinnön mukainen yhdiste vapaassa muodossa tai maataloudellisesti hyväksyttävän suolan tai metal-likompleksin muodossa sopii myös käytettäväksi kasvitauteja aiheuttavia sieniä vastaan. Tämä sieniä hävittävä aktiivisuus voidaan osoittaa mm. in vivo- kokeilla 15 leikkopavuissa olevaa Uromyces appendiculatusta (papu-ruoste) vastaan, kuin myös muita kahvissa, vehnässä, pellavassa ja koristekasveissa (esim. pelargonia, lei-jonankita) esiintyviä ruostesieniä (esim. Hemileia, Puccinia) vastaan; kurkussa olevaa Erysiphe cichora-20 cearumia vastaan, kuin myös muita vehnässä, ohrassa, omenassa ja viiniköynnöksessä esiintyviä homepölyjä (esim. E. Graminis f. sp.tritici. E. gram. f. sp. hor-dei, Podosphaera leucotricha, Uncinula recator) vastaan.
25 Seuraava esimerkki havainnollistaa keksintöä.
Kaikki lämpötilat on annettu asteina celsiusta. ESIMERKKI 1; N-Metwli-N-(l-naftyylimetyvli)-4-(2-fe-nwli-2-propwli) bentsyyliamiini
Grignard-reagenssi valmistetaan 3 g 2-(4-bro-30 mofenyyli)-2-fenyylipropaanista ja 265 mg magnesiumista 25 ml eetterissä. 2.5 g N-etoksimetyyli-N-metyyli--1-naftyylimetyyliamiinia 5 ml eetterissä lisätään seokseen tipoittain huoneen lämpötilassa samalla seosta voimakkaasti sekoittaen, jonka jälkeen seosta refluk-35 soidaan 4 h ajan. Tämän jälkeen lisätään kyllästettyä ammoniumkloridin vesiliuosta ja 1/2 h sekoituksen jälkeen vesifaasia uutetaan eetterillä. Yhdistetyt 5 8 y / G / orgaaniset faasit kuivataan ja liuos tislataan pois. Pyiväskromatografiällä silikageelissä (eluenttina tolu-eeni/etyyliasetaatti = 95/5) saadaan puhdas tuote öljy- nä.
5 Tarvittava lähtöaine voidaan valmistaa esim.
seuraavasti: A) N-etoksimetyyli-N-metyyli-l-naftyylimetyy- liamiini.
21 g N-metyyli-l-naftyylimetyyliamiinia ja 9 g 10 abs. etanolia käsitellään jäähauteessa vähin erin 3.6 g paraformaldehydillä ja seosta sekoitetaan 1 h ajan huoneen lämpötilassa. Reaktioseosta käsitellään dikloo-rimetaanilla, se suodatetaan ja konsentroidaan. Puhdas tuote saadaan vaaleankeltaisena öljynä vaakuumitislauk-15 sen jälkeen (1.3 mbar/135-138°).
NMR-spektrit
Esim. spektri 20 1 8.10-8.34 (m,lH); 7.64-7.95 (m, 2H); 7.03-7.58 (m, 13H); 3.92 (s, 2H); 3.55 (s, 2H); 2.19 (s, 3H); L65 (s, 6H).
:*·; A 8.05-8.35 (m, iH); 7.15-8.0 (rn, 6H); 4.15 (s, 4Hj;. 3.48 (qua, J = -··. 7 Hz. 2H); 2.45 (s, 3H); 1.2 (t, J = 7 Hz, 3H).
Claims (2)
1. Förfarande för framställning av en tera-peutiskt användbar N-raetyl-N-(1-naftylmetyl)-4-(2-fe-5 nyl-2-propyl)benzylamin i fri basform eller i form av ett syraadditionssalt, kännetecknat därav, att i) en förening, enligt formel VI, ch3 10 i . N CH-7 - OR cd ‘ väri R är en lägre alkyl, fär reagera med en förening, 15 enligt formel VII ch3 Me “O-1 -O m ch3 20 väri Me är en metallekvivalent, eller ii) en förening, enligt formel Via, ch3 ch3 25 ro-ch2 -n - ch2 —^C —^J) 714 ch3 väri R är detsamma som ovan, fär reagera med en förening, enligt formel Vila 30 Me _ I VIIa 35 väri Me är det samma som ovan, och att den pä detta sätt erhällna N-metyl-N-(1-naftyl-metyl)-4-(2-fenyl-2-propyl)benzylaminen tas tillvara i 9 r\ n C- «“? 8 y / u / fri form eller i form av ett syraadditionssalt.
* 2. Förfarande enligt patentkrav 1, k ä n - netecknat därav, att den erhällna föreningen tas tillvara i form av syraadditionssaltet.
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3602579 | 1986-01-29 | ||
| DE3602579 | 1986-01-29 | ||
| DE3609123 | 1986-03-19 | ||
| DE3609123 | 1986-03-19 | ||
| DE3617637 | 1986-05-26 | ||
| DE3617635 | 1986-05-26 | ||
| DE3617637 | 1986-05-26 | ||
| DE3617635 | 1986-05-26 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI870342A0 FI870342A0 (fi) | 1987-01-27 |
| FI870342A FI870342A (fi) | 1987-07-30 |
| FI89707B true FI89707B (fi) | 1993-07-30 |
| FI89707C FI89707C (fi) | 1993-11-10 |
Family
ID=27433512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI870342A FI89707C (fi) | 1986-01-29 | 1987-01-27 | Foerfarande foer framstaellning av en ny aminderivata |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US4939148A (fi) |
| KR (1) | KR920010574B1 (fi) |
| AT (1) | AT398761B (fi) |
| AU (1) | AU607694B2 (fi) |
| BE (1) | BE1001550A5 (fi) |
| CA (1) | CA1329619C (fi) |
| CH (1) | CH672875A5 (fi) |
| CY (1) | CY1726A (fi) |
| DK (1) | DK46387A (fi) |
| ES (1) | ES2004079A6 (fi) |
| FI (1) | FI89707C (fi) |
| FR (1) | FR2597475B1 (fi) |
| GB (1) | GB2185980B (fi) |
| GR (1) | GR870127B (fi) |
| HK (1) | HK110193A (fi) |
| HU (1) | HU211997B (fi) |
| IE (1) | IE59490B1 (fi) |
| IL (1) | IL81410A (fi) |
| LU (1) | LU86745A1 (fi) |
| NL (1) | NL8700083A (fi) |
| NZ (1) | NZ219069A (fi) |
| PT (1) | PT84199B (fi) |
| SE (1) | SE8700328L (fi) |
| SG (1) | SG63593G (fi) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5334628A (en) * | 1984-06-09 | 1994-08-02 | Kaken Pharmaceutical Co., Ltd. | Amine derivatives, processes for preparing the same and fungicides containing the same |
| JPS6145A (ja) * | 1984-06-09 | 1986-01-06 | Kaken Pharmaceut Co Ltd | Ｎ‐（４‐ｔｅｒｔ‐ブチルベンジル）‐Ｎ‐メチル‐１‐ナフチルメチルアミンおよびそれを有効成分とする抗真菌剤 |
| JP2581707B2 (ja) * | 1987-10-02 | 1997-02-12 | 科研製薬株式会社 | 抗真菌剤組成物 |
| NZ227042A (en) * | 1987-11-27 | 1991-05-28 | Banyu Pharma Co Ltd | Substituted alkylamine derivatives and pharmaceutical compositions |
| US5234946A (en) * | 1987-11-27 | 1993-08-10 | Banyu Pharmaceutical Co., Ltd. | Substituted alkylamine derivatives |
| IL89028A0 (en) * | 1988-01-29 | 1989-08-15 | Lilly Co Eli | Quinoline,quinazoline and cinnoline derivatives |
| IL89029A (en) * | 1988-01-29 | 1993-01-31 | Lilly Co Eli | Fungicidal quinoline and cinnoline derivatives, compositions containing them, and fungicidal methods of using them |
| DE3838631A1 (de) * | 1988-11-15 | 1990-05-23 | Basf Ag | Neue 2-aminodekalin-derivate und deren verwendung |
| US5239084A (en) * | 1990-06-29 | 1993-08-24 | Hoffmann-La Roche Inc. | Substituted aminoalkyl biphenyl compounds |
| CA2044533A1 (en) * | 1990-06-29 | 1991-12-30 | Philippe Guerry | Substituted aminoalkylbiphenyl derivatives |
| FR2664592B1 (fr) * | 1990-07-10 | 1994-09-02 | Adir | Nouveaux derives de la piperidine, de la tetrahydropyridine et de la pyrrolidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| US6117884A (en) * | 1997-07-31 | 2000-09-12 | Daeuble; John | 4-substituted quinoline derivatives having fungicidal activity |
| CN108047057B (zh) * | 2017-12-28 | 2020-06-02 | 山东铂源药业有限公司 | 一种布替萘芬的合成方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1109924A (en) * | 1965-11-29 | 1968-04-18 | Roche Products Ltd | Novel substituted diphenylalkyl amines and a process for the manufacture thereof |
| US3598839A (en) * | 1969-06-30 | 1971-08-10 | Parke Davis & Co | Phenylbenzothiophene compounds |
| DE2048147A1 (de) * | 1969-10-01 | 1971-04-08 | E R Squibb & Sons Ine , New York, NY (VStA) | Acenaphthylderivate, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US3862330A (en) * | 1971-03-18 | 1975-01-21 | Robert P Johnson | N-(c{hd 8{b -c{hd 12 {b alkyl) diaralkylamines used to combat plant fungi |
| DE19375084I2 (de) * | 1979-08-22 | 2000-11-16 | Novartis Ag | Propenylamine Verfahren zu ihrer Herstellung sie enthaltende pharmazeutische Zusammensetzungen und ihre Verwendung als Arzneimittel |
| US4552960A (en) * | 1983-06-20 | 1985-11-12 | Eli Lilly And Company | Fungicidal amines |
| JPS6145A (ja) * | 1984-06-09 | 1986-01-06 | Kaken Pharmaceut Co Ltd | Ｎ‐（４‐ｔｅｒｔ‐ブチルベンジル）‐Ｎ‐メチル‐１‐ナフチルメチルアミンおよびそれを有効成分とする抗真菌剤 |
| JPH0617341B2 (ja) * | 1985-06-08 | 1994-03-09 | 科研製薬株式会社 | アミン化合物およびそれを有効成分とする抗真菌剤 |
| US4761424A (en) * | 1985-10-01 | 1988-08-02 | Warner-Lambert Company | Enolamides, pharmaceutical compositions and methods for treating inflammation |
| JPH0676285B2 (ja) * | 1985-11-01 | 1994-09-28 | 三井東圧化学株式会社 | ベンジルアミン誘導体、その製造法およびその用途 |
-
1987
- 1987-01-15 HU HU87117A patent/HU211997B/hu not_active IP Right Cessation
- 1987-01-15 NL NL8700083A patent/NL8700083A/nl not_active Application Discontinuation
- 1987-01-23 CH CH244/87A patent/CH672875A5/de not_active IP Right Cessation
- 1987-01-26 GB GB8701646A patent/GB2185980B/en not_active Expired - Lifetime
- 1987-01-26 FR FR878700973A patent/FR2597475B1/fr not_active Expired - Fee Related
- 1987-01-27 PT PT84199A patent/PT84199B/pt not_active IP Right Cessation
- 1987-01-27 IE IE20787A patent/IE59490B1/en not_active IP Right Cessation
- 1987-01-27 KR KR1019870000706A patent/KR920010574B1/ko not_active IP Right Cessation
- 1987-01-27 GR GR870127A patent/GR870127B/el unknown
- 1987-01-27 NZ NZ219069A patent/NZ219069A/en unknown
- 1987-01-27 FI FI870342A patent/FI89707C/fi not_active IP Right Cessation
- 1987-01-27 BE BE8700051A patent/BE1001550A5/fr not_active IP Right Cessation
- 1987-01-28 SE SE8700328A patent/SE8700328L/xx not_active Application Discontinuation
- 1987-01-28 DK DK046387A patent/DK46387A/da not_active Application Discontinuation
- 1987-01-28 AT AT0015987A patent/AT398761B/de not_active IP Right Cessation
- 1987-01-28 LU LU86745A patent/LU86745A1/fr unknown
- 1987-01-28 IL IL81410A patent/IL81410A/xx not_active IP Right Cessation
- 1987-01-29 US US07/008,198 patent/US4939148A/en not_active Expired - Lifetime
- 1987-01-29 AU AU68119/87A patent/AU607694B2/en not_active Ceased
- 1987-01-29 ES ES8700212A patent/ES2004079A6/es not_active Expired
- 1987-01-29 CA CA000528508A patent/CA1329619C/en not_active Expired - Fee Related
-
1990
- 1990-05-08 US US07/520,577 patent/US5112851A/en not_active Expired - Fee Related
-
1993
- 1993-05-13 SG SG63593A patent/SG63593G/en unknown
- 1993-10-21 HK HK1101/93A patent/HK110193A/xx not_active IP Right Cessation
-
1994
- 1994-05-06 CY CY172694A patent/CY1726A/xx unknown
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Legal Events
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| BB | Publication of examined application | ||
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: SANDOZ AG |