SE447381B - Nya n-aryloxazolidinoner och pyrrolidinoner - Google Patents
Nya n-aryloxazolidinoner och pyrrolidinonerInfo
- Publication number
- SE447381B SE447381B SE8001674A SE8001674A SE447381B SE 447381 B SE447381 B SE 447381B SE 8001674 A SE8001674 A SE 8001674A SE 8001674 A SE8001674 A SE 8001674A SE 447381 B SE447381 B SE 447381B
- Authority
- SE
- Sweden
- Prior art keywords
- formula
- group
- compound
- carbon atoms
- pyrrolidinones
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D277/14—Oxygen atoms
Description
447 381
(I)
där kombinationen (X. A. RI) har följande betydelser:
(O. CH2. H). varvid R2 = CHZOH och R = p-(meta-
-nitro)bensyloxí. eller
(0. 0, H), varvid R2 = CHZORÖ. där R6 = lin-
jär eller grenad alkyl med 1 - S kolatomer eller
cyklohexyl och R är en av följande grupper i para-
ställning: linjär eller grenad alkyloxi med 4 - 6
kolatomer: cykloalkylmetoxi. vars alkylrest inne-
håller 4 - 7 kolatomer: (metyl-l-cyklopenty1-l)-
metoxi; buten-2-oxi: metyl-3-buten-2-oxi; (%yklopen-
ten-1-y1)metoxi; (cyklohexen-1-yl)metoxi: morfolino-
-2-etoxi; klor-4-butyloxi: (oxo-4-cyk1ohexyl-l)-
metoxí; oxo-2-propoxi: cyano-3-propoxí: Qyano-4-
-butoxi; dimetylamino; (tetrahydropyranyl-4)metoxi:
(tetrahydropyranyl-3)metoxí, bensyloxi med formeln
(ICE-Rv, aa: m7 = n, s-cl, 4-c1. a-r. a-F.
3-I, 3-BI, 3-CF3. 3-N02, 4-N02. 3-CN, 4-CN: ben-
syloxí, disubstituerad. med formeln
. R
f 8
0//\LÉšï[:F varvid Ra Cl. CN eller N02;
f l _
0 f/ C varvid R Cl eller NO : eller
O R 9 2
0 2 varvid Rs _ Cl eller CN;
s
cl
o/\
cl
Föreningarna med formel (I) erhålles t.ex. genom
f
447 381
3
kondensation av föreningar enligt föreliggande uppfinning med
/-
ao __@_N o
Y (IIA)
i o
formeln
där R'6 betecknar en linjär eller grenad alkylgrupp med 1-5
kolatomer, cyklohexyl eller metoximetyl, med vissa klorider
eller p~tosylater med formeln:
R' ~c1)
20
R'2O- OTS )
såsom beskrives närmare i huvudpatentet.
Kondensationen genomföras under återflöde i aceton
eller acetonitril i närvaro av kaliumkarbonat eller under åter-
flöde i dimetylformamid i närvaro av natriumhydrid. g
Föreningarna med formeln (IIA) enligt uppfinningen
erhålles själva genom hydrogenolys i närvaro av palladium på
kol av föreningar enligt uppfinningen med formeln:
där R'6 har samma betydelser som i formel (IIA).
Föreningarna (IIB) erhålles i sin tur genom en syntes i
tre steg, bestående av kondensation av klorhydrin med formeln:
Cl
Om (x)
OH
där R'6 har samma betydelser som i formeln (IIB), med fosgen,
varefter den således erhållna "råa" reaktionsprodukten konden-
seras med para-bensyloxianilin och den därvid erhållna råpro-
dukten cykliseras med etanolisk kaliumhydroxid eller natrium-
metylat i metanolisk lösning.
Enligt en annan utföringsform, som beskrivits närmare
i huvudpatentet, erhålles föreningarna med formeln (I) då R
betecknar den speciella gruppen
447 381
4
cyano-2-etoxi, medelst en reaktion mellan akrylonitril och
en förening enligt föreliggande uppfinning med formeln (IïA)
i närvaro av triton B.
Föreningen med formeln (I), där symbolerna (X, A, Rl)
ihar betydelserna (O, CH2, H), varvid R? betecknar en hydroxi-
metylgrupp och R betecknar en para-(metanitro)-bensyloxi-
grupp, erhålles genom inverkan av metanitrobensylklorid på en
förening enligt föreliggande uppfinning med formeln:
OH
HO (IIC)
I
o
_ Föreningen (IIC) enligt föreliggande uppfinning er-
hålles genom hydrogenolys i närvaro av palladium på kol av
en förening enligt uppfinningen med formeln
D OH
0
Föreningen (IID) enligt uppfinningen erhålles själv
genom reduktion medelst litiumborhydrid av en förening enligt
uppfinningen med formeln
COÛEÜ
<3:š:>//\\\O___“<::::>""š:;;:S: (IIE)
Föreningen enligt uppfinningen med formeln (IIE) erhålles
själv genom förestring medelst etanol i närvaro av svavelsyra
av en förening enligt uppfinningen med formeln
COOH
@^po (m)
Föreningen (IIF) enligt uppfinningen erhålles genom
kondensation av parabensyloxianilin med itakonsyra.
Föreningen med formeln (I), där symbolerna (X, A, Rl) har
betydelserna (H2, cH2, H), varvid R2 betecknar en hyaroxi-
447 381
metylgrupp och R betecknar en parabensyloxiarupp, erhålles genom
reduktion medelst litium-dubbelhydrid och aluminium av en
förening med formeln (IIE) enligt uppfinningen.
Exempel l
para-n-butyloxífeny1-3-isopropyloximetyl-5«oxazolidinon-
-2 ßfl
Steg l: para-bensyloxifenyl-3-isopropyl-oximetyl-5~oxazolidinon-
-2 ÉIÉ] enligt uppfinningen.
_ Till en lösning av 59 g fosgen i 560 ml díkloretan
satte man 83,U g klor-l-isopropyloxi-3-propanol-2 BXÜ och
därefter under loppet av 30 minuter en lösning av 81,9 g
N,N-dietylanilin i 160 ml dikloretan, varefter värmdes till
5000 under 2 timmar och sedan tillsattes 250 ml vatten, var-
efter den oréaniska fasen avdekanterades och denna under loppet
av 50 minuter sattes till 217,5 å Éara-bensyloxianilin. Man
höll blandningen 3 timmar under återflödesvärmning varefter
filtrerades och tvättades med en lösning av lN klorvätesyra
i vatten, torkades, lösningsmedlet avdrevs och återstoden om-
kristalliserades ur etanol. Man isolerade på detta sätt 165,5
g av den eftersökta produkten.
Utbyte: 81 %
smältpunktz 1o7°c
RMN-spektrum: Ö ppm (nmso)
9,80,s, -NH-COO- 1 proton
7,U0,s, och 5,08,s 7 protoner
7,l8,m, aromatiska protoner U protoner
5,2o,m, -o-cqj 1 proton
H
3,85,d, (J=5Hz) -CH2-O- 2 protoner
5,59,m, Cl-CH2-CH- 5 protoner
CH3
l,O6,d, (J=7Hz)-O\\
6 protoner
CH5
IR-spektrum: NH-C00-band vid l700 och 3305 cm-
En lösning av 165,5 g av den erhållna föreningen och
29,5 g kaliumhydroxid i 2,N liter etanol hölls 5 timmar vid
5000. Man avdrev sedan lösningsmedlet, upptog återstoden i
kloroform, tvättade med vatten, torkade och avdrev lösnings-
medlet. Därefter kristalliserades återstoden i eter och om-
kristalliserades ur dioxan, varvid man erhöll 113 g av den
l
eftersökta produkten.
Utbyte: 75 z
smä1tpunkt= 11o°c
447 381
6
Bruttoformel: CQOHQBNOÄ
Molekylvikt: 5Ul,H
Elementaranalys:
C H N
Beräknat: (%) 70,36 6,79 U,l0
Ernå11et= (%) 70,1u 6,u9 u,22
Medelst samma förfarande men utgående från resp.
reaktionskomponenter erhöll man föreningarna med formel (IIB) i
nedanstående tabell I med de interna beteckninaarna 226-229.
§teg 2: parahydroxifenyl-3-isopropyloXimetyl-5-oxa-zolidinon-2
(IIA)
Beteckning: 221
En lösning av 85 g av den i föregående steg erhållna
föreningen 1 1700 mi aioxan samt 15 mi 6,5 N an«m0iisa;k1orväfie
hydrogenolyserades i autoklav under ett tryck av 6 kp under
6 timmar i närvaro av 8,5 g 10-procentig palladium på kol. Man
ffltrerade sedan,avdrev lösningsmedlet, krístalliserade åter-
stoden i eter och omkristalliserade ur toluen. På detta sätt
isolerade man H3,7 g av den eftersökta produkten.
Utbyte: 70 %
smä1tpunkt=.93°c
Bruttoformel: Cl3Hl?NOu
- Molekylvikt: 251,3
Elementaranalys:
c H N
Beräknat: (%) 62,14 6,82 5,57
Erhå11et= (%) 62,1u 6,80 5,56
Medelst samma förfarande men utgående från resp.
reaktionskomponenter erhöll man föreningarna med formel (IIA)
i nedanstående tabell II med beteckninaarna 222-22Ä samt 230-232.
Exempel 2
N-parabensyloxifenyl~l-hydroximetyl-U-pyrrolidinon-2-
ÜID].
Steg l: [(N-parabensyloxífenyl-pyrrolidinon-2)yl-Ä]-karboxylsyra
fiïfifl.
En blandning av Ä6 g itakonsyra och 70 g parabensgl-
oxianilin i H00 ml vatten hölls under återflöde. Man filtrerade,
'tvättade påifiItret9med¿klonoform¿ torkade och omkristallisera-
'de produkten ur aceton. Man erhöll 77 g av den eftersökta före-
ningen.
Utbyte: 7l %
447 381
7
smältpunxtz 19u°c- i_
Bruttoformel: Cl8Hl7NOu
Molekylvikt: 311,32
Elementaranalys:
C H N
Beräknat: (%) 69,Dü 5,50 U,50
Erhället: (%) 69,69 5,u8 u,8o
Steg 2:
ÜN~parabensyloxifenyl-pyrrolidinon-2)-yl-U]-etyl~
karb oxylat [IIE] .
En lösning av BN g av den i föregående steg erhållna
syran i 400 ml etanol och 6 ml koncentrerad svavelsyra hölls
2 timmar under återflöde. Man omkristalliserade sedan, avfilt-
rerade fällningen, tvättade med vatten och torkade samt om-
krístalliserade produkten ur isopropanol. Man erhöll på detta
sätt U7 g av den eftersökta produkten.
Utbyte: 51 %
smä1tpunkt= 1o6°c
Bruttoformelz CZOHEINOÄ
Molekylvikt: 339,38
Elementaranalys:
C H N
Beräknat: (%) 70,78 6,2u u,13
Erhälletz (1) 70,96 6,59 u,uu
Steg 3: '
N-para-bensyloxifenyl-l-hydroximetyl-H-pyrrolidinon-2
[11rfl. 7
Till en blandning av 7,9 Q natriumborhydrid och 18 g
litiumbromid i H00 ml diglym satte man 70 g av den i föregående
steg erhållna föreningen.
Man höll blandningen 50 minuter vid 10000, utspädde
med 500 g is och 50 ml koncentrerad klorvätesyra, extraherade
med kloroform, indunstade lösningsmedlet, krístalliserade
återstoden i isopropyleter och omkristallíserade produkten ur
toluen. Man erhöll på detta sätt H5 g av den eftersökta pro-
dukten.
Utbyte: 72 %
Smältpunkt: llO°C
Bruttoformel: Cl8Hl9NO3
Molekylvikt: 297,3ä
4470381
8
Elementaranalys:
C H N
Beräknat: (%) 72,70 6,H4 H,7l
efirnäilet: (%) 2 72,uu 6,36 u,68
Exempel 5
Nfimrabensylcxifenyl-hydroxímetyl-5'DYrrolídin [I]
Intern beteckning 220
En lösning av 53 2 av föreningen med formel IÄIEÛ
erhållen enligt exempel 2, i 300 ml vattenfri tetrahydrofuran
sattes under kylning till ll,8 g lítium-dubbelhydrid och
aluminium (i tablettform) i 1000 ml tetrahydrofuran och
blandningen hölls 2 timmar under återflöde varefter man
successivt tillsatte 6,3 ml vatten, 4,75 ml natriumhydroxid
(20 %íg) och slutligen 22 ml vatten. Man filtrerade, in-
dunstade filtratet och kristalliserade återstoden ur etyl-
acetat. Man erhöll på detta sätt 38 g av den eftersökta
produkten.
Utbyte; 85 %
smältpunktz 87°c
Bruttoformel: Cl8H2lNO2
Elementaranalys:
C H N
Beräknat: (%) 76,29 7,H7 K ü,94
Ernålietz (%) 76,Uo 7,60 H,65
447 381
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4417 381
10
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447 381
11
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Claims (1)
- 447 381 Nya kemiska föreningar, Patefiïkrav f k ä n n e t e c K n a d e av den allmänna formeln u, f-TB QÅY där A betecknar: en väteatom. varvid Y betecknar en syreatom och B betecknar en grupp med formeln CH20R'6, där R'6 grenad alkylgrupp med 1 - 5 kolatomer eller en cyklo- är en linjär eller hexylgrupp eller Y betecknar en CH2-grupp och B betecknar en hydroximetylgrupp eller A betecknar: en bensylgruvp. varvid Y betecknar en syreatom och B betecknar en grupp med formeln CH2OR'6. där R'6 är en linjär eller grenad alkylgrupp med 1 - 5 kolatomer. eller Y be- tecknar en CH2~grupp och B betecknar en hydroxi- metyl-, etoxikarbonyl- eller karboxylgrupp.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7817388A FR2428032A1 (fr) | 1978-06-09 | 1978-06-09 | Nouvelles oxazolidimones, oxazolidinethiones et pyrrolidinones, leur procede de preparation et leur application en therapeutique |
FR7824024A FR2435473A2 (fr) | 1978-08-17 | 1978-08-17 | Nouvelles n-aryle oxazolidinones, oxazolidinethiones et pyrrolidinones, leur procede de preparation et leur application en therapeutique |
Publications (2)
Publication Number | Publication Date |
---|---|
SE8001674L SE8001674L (sv) | 1980-03-04 |
SE447381B true SE447381B (sv) | 1986-11-10 |
Family
ID=26220626
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SE7904970A SE446733B (sv) | 1978-06-09 | 1979-06-07 | Nya n-aryloxazolidinoner, oxazolidintioner, pyrrolidinoner, pyrrolidiner och tiazolidinoner och sett att framstella desamma samt kompositioner derav |
SE8001674A SE447381B (sv) | 1978-06-09 | 1980-03-04 | Nya n-aryloxazolidinoner och pyrrolidinoner |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SE7904970A SE446733B (sv) | 1978-06-09 | 1979-06-07 | Nya n-aryloxazolidinoner, oxazolidintioner, pyrrolidinoner, pyrrolidiner och tiazolidinoner och sett att framstella desamma samt kompositioner derav |
Country Status (13)
Country | Link |
---|---|
US (5) | US4348393A (sv) |
AU (1) | AU525787B2 (sv) |
BE (1) | BE876831A (sv) |
CA (1) | CA1129859A (sv) |
CH (2) | CH642069A5 (sv) |
DE (1) | DE2923295A1 (sv) |
ES (5) | ES481909A0 (sv) |
GB (2) | GB2054575B (sv) |
GR (1) | GR69969B (sv) |
IT (2) | IT1206305B (sv) |
LU (1) | LU81370A1 (sv) |
NL (1) | NL7904528A (sv) |
SE (2) | SE446733B (sv) |
Families Citing this family (47)
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US4348393A (en) * | 1978-06-09 | 1982-09-07 | Delalande S.A. | N-Aryl oxazolidinones, oxazolidinethiones, pyrrolidinones, pyrrolidines and thiazolidinones |
CA1171865A (en) * | 1980-06-04 | 1984-07-31 | Alain Lacour | N-aryl azolone derivatives, the process for preparing the same and their application in therapeutics |
US4340606A (en) * | 1980-10-23 | 1982-07-20 | E. I. Du Pont De Nemours And Company | 3-(p-Alkylsulfonylphenyl)oxazolidinone derivatives as antibacterial agents |
FR2500450A1 (fr) * | 1981-02-25 | 1982-08-27 | Delalande Sa | Nouveaux derives aminomethyl-5 oxazolidiniques, leur procede de preparation et leur application en therapeutique |
FR2528046B1 (fr) * | 1982-06-08 | 1985-06-21 | Delalande Sa | Derives de l'oxazolidinone-2 n-arylee optiquement actifs, inhibiteurs specifiques et reversibles de la monoamine oxydase de type b et leur procede de preparation |
US4461773A (en) * | 1982-09-15 | 1984-07-24 | E. I. Dupont De Nemours And Company | P-Oxooxazolidinylbenzene compounds as antibacterial agents |
ES533097A0 (es) * | 1983-06-07 | 1985-08-01 | Du Pont | Un procedimiento para la preparacion de nuevos derivados del amino-metil-oxooxazolidinil-benzeno. |
US4705799A (en) * | 1983-06-07 | 1987-11-10 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl benzenes useful as antibacterial agents |
HU191408B (en) * | 1984-04-25 | 1987-02-27 | Egis Gyogyszergyar,Hu | Process for preparing new imino-thiazolidine derivatives |
USRE34242E (en) * | 1986-04-29 | 1993-05-04 | Akzo N.V. | Amino-oxazole compounds having dopaminergic activity |
GB8610432D0 (en) * | 1986-04-29 | 1986-06-04 | Akzo Nv | Amino-thiazole & oxazole derivatives |
US4897409A (en) * | 1986-09-03 | 1990-01-30 | Delalande S.A. | 5-aminoethyloxazolidin-2-one derivatives |
SE8801518D0 (sv) * | 1988-04-22 | 1988-04-22 | Astra Pharma Prod | A novel process |
US4876352A (en) * | 1988-09-14 | 1989-10-24 | Schering Corporation | Pressurized fluorination of hydroxy alkyl groups |
US4933463A (en) * | 1989-05-08 | 1990-06-12 | Gaf Chemicals Corporation | Polymerizable pyrrolidonyl oxazoline monomers, homopolymers and copolymers |
US5235063A (en) * | 1989-10-17 | 1993-08-10 | Delalande S.A. | Process of preparing by condensation certain |
FR2653017B1 (fr) * | 1989-10-17 | 1995-05-05 | Delalande Sa | Derives d'aryl-3 oxazolidinone-2, leur procede de preparation et leur application en therapeutique. |
US5196543A (en) * | 1989-10-17 | 1993-03-23 | Delalande S.A. | 3-aryloxazolidinone derivatives, process for their preparation and their use in therapy |
US5182296A (en) * | 1989-10-26 | 1993-01-26 | Tanabe Seiyaky Co., Ltd. | Naphthyloxazolidone derivatives |
CZ288351B6 (en) * | 1990-06-07 | 2001-05-16 | Astrazeneca Ab | Nitrogenous heterocyclic compound, process of its preparation and use as well as a medicament containing thereof |
FR2675504B1 (fr) * | 1991-04-16 | 1995-01-27 | Delalande Sa | Derives d'aryl-3 oxazolidinone, leur procede de preparation et leur application en therapeutique. |
JPH0559022A (ja) * | 1991-09-05 | 1993-03-09 | Nippon Paint Co Ltd | 5位に置換基を有する2−オキサゾリジノン化合物 |
US5688792A (en) * | 1994-08-16 | 1997-11-18 | Pharmacia & Upjohn Company | Substituted oxazine and thiazine oxazolidinone antimicrobials |
TW286317B (sv) * | 1993-12-13 | 1996-09-21 | Hoffmann La Roche | |
GB9601666D0 (en) * | 1996-01-27 | 1996-03-27 | Zeneca Ltd | Chemical compounds |
GB9702213D0 (en) | 1996-02-24 | 1997-03-26 | Zeneca Ltd | Chemical compounds |
GB9609919D0 (en) * | 1996-05-11 | 1996-07-17 | Zeneca Ltd | Chemical compounds |
GB9717807D0 (en) | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
GB9717804D0 (en) | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
GB9725244D0 (en) | 1997-11-29 | 1998-01-28 | Zeneca Ltd | Chemical compounds |
WO1999064417A2 (en) * | 1998-06-05 | 1999-12-16 | Astrazeneca Ab | Oxazolidinone derivatives, process for their preparation and pharmaceutical compositions containing them |
GB9928568D0 (en) | 1999-12-03 | 2000-02-02 | Zeneca Ltd | Chemical compounds |
GB0009803D0 (en) * | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
US6525202B2 (en) * | 2000-07-17 | 2003-02-25 | Wyeth | Cyclic amine phenyl beta-3 adrenergic receptor agonists |
US6498170B2 (en) | 2000-07-17 | 2002-12-24 | Wyeth | Cyclamine sulfonamides as β-3 adrenergic receptor agonists |
US6465501B2 (en) | 2000-07-17 | 2002-10-15 | Wyeth | Azolidines as β3 adrenergic receptor agonists |
US6537994B2 (en) | 2000-07-17 | 2003-03-25 | Wyeth | Heterocyclic β3 adrenergic receptor agonists |
US6410734B1 (en) * | 2000-07-17 | 2002-06-25 | Wyeth | 2-substituted thiazolidinones as beta-3 adrenergic receptor agonists |
WO2002018354A1 (en) * | 2000-08-31 | 2002-03-07 | Abbott Laboratories | Oxazolidinones and their use as antibacterial agents |
PA8583001A1 (es) * | 2002-09-20 | 2004-04-23 | Hoffmann La Roche | Derivados de 4-pirrolidino-fenil-bencil eter como inhibidores de mao-b |
SG2009082793A (en) | 2003-06-03 | 2015-03-30 | Rib X Pharmaceuticals Inc | Biaryl heterocyclic compounds and methods of making and using the same |
US8324398B2 (en) | 2003-06-03 | 2012-12-04 | Rib-X Pharmaceuticals, Inc. | Process for the synthesis of biaryl oxazolidinones |
US7148362B2 (en) * | 2003-09-18 | 2006-12-12 | Hoffmann-La Roche Inc. | Process for the preparation of enantiopure pyrrolidin-2-one derivatives |
CN100441188C (zh) * | 2003-10-23 | 2008-12-10 | 弗·哈夫曼-拉罗切有限公司 | 作为mao-b抑制剂的苯并氮杂衍生物 |
WO2005061468A1 (en) * | 2003-12-17 | 2005-07-07 | Rib-X Pharmaceuticals, Inc. | Halogenated biaryl heterocyclic compounds and methods of making and using the same |
US7501528B2 (en) * | 2005-03-15 | 2009-03-10 | Hoffmann-La Roche Inc. | Method for preparing enantiomerically pure 4-pyrrolidino phenylbenzyl ether derivatives |
JP5534497B2 (ja) | 2005-06-08 | 2014-07-02 | メリンタ セラピューティクス,インコーポレイテッド | トリアゾール類の合成方法 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1180089A (en) * | 1967-10-20 | 1970-02-04 | Delalande Sa | Acetylenic Derivatives of 2-Oxazolidinones and processes of preparation |
GB1222708A (en) * | 1968-10-22 | 1971-02-17 | Delalande Sa | Novel 5-(n-substituted aminomethyl)-2-oxazolidinones and their process of preparation |
GB1252101A (sv) | 1969-03-18 | 1971-11-03 | ||
US4062862A (en) * | 1975-07-04 | 1977-12-13 | Nippon Chemiphar Co., Ltd. | 5-Benzyl-2-oxazolidone derivatives and a process for producing the same |
FR2356422A1 (fr) * | 1976-03-01 | 1978-01-27 | Delalande Sa | Nouveaux hydroxymethyl-5 oxazolidinone-2, leur procede de preparation et leur application en therapeutique |
SU888821A3 (ru) * | 1976-12-03 | 1981-12-07 | Шеринг Аг (Инофирма) | Способ получени 5-(замещенный фенил)-оксазолидинонов или их серусодержащих аналогов |
FR2380780A2 (fr) | 1977-02-22 | 1978-09-15 | Delalande Sa | Application en therapeutique des hydroxymethyl-5 oxazolidinones-2, notamment comme antidepresseurs |
LU80081A1 (fr) | 1977-08-26 | 1979-05-15 | Delalande Sa | Nouvelles hydroxymethyl-5 oxazolidinones-2,leur procede de preparation et leur application therapeutique |
US4348393A (en) * | 1978-06-09 | 1982-09-07 | Delalande S.A. | N-Aryl oxazolidinones, oxazolidinethiones, pyrrolidinones, pyrrolidines and thiazolidinones |
CA1171865A (en) | 1980-06-04 | 1984-07-31 | Alain Lacour | N-aryl azolone derivatives, the process for preparing the same and their application in therapeutics |
-
1979
- 1979-06-04 US US06/045,143 patent/US4348393A/en not_active Expired - Lifetime
- 1979-06-06 LU LU81370A patent/LU81370A1/fr unknown
- 1979-06-06 CA CA329,220A patent/CA1129859A/en not_active Expired
- 1979-06-07 SE SE7904970A patent/SE446733B/sv not_active IP Right Cessation
- 1979-06-07 AU AU47862/79A patent/AU525787B2/en not_active Ceased
- 1979-06-07 GR GR59290A patent/GR69969B/el unknown
- 1979-06-07 BE BE0/195621A patent/BE876831A/xx not_active IP Right Cessation
- 1979-06-08 GB GB8021771A patent/GB2054575B/en not_active Expired
- 1979-06-08 GB GB7920102A patent/GB2028306B/en not_active Expired
- 1979-06-08 DE DE19792923295 patent/DE2923295A1/de active Granted
- 1979-06-08 ES ES481909A patent/ES481909A0/es active Granted
- 1979-06-08 IT IT7923395A patent/IT1206305B/it active
- 1979-06-08 CH CH540079A patent/CH642069A5/fr not_active IP Right Cessation
- 1979-06-08 NL NL7904528A patent/NL7904528A/xx not_active Application Discontinuation
-
1980
- 1980-02-06 US US06/119,073 patent/US4287351A/en not_active Expired - Lifetime
- 1980-03-04 SE SE8001674A patent/SE447381B/sv not_active IP Right Cessation
- 1980-03-19 CH CH216180A patent/CH639962A5/fr not_active IP Right Cessation
- 1980-03-31 ES ES490112A patent/ES8102105A1/es not_active Expired
- 1980-03-31 ES ES490113A patent/ES490113A0/es active Granted
- 1980-03-31 ES ES490114A patent/ES8101060A1/es not_active Expired
- 1980-03-31 ES ES490110A patent/ES8106509A1/es not_active Expired
- 1980-05-23 IT IT8022284A patent/IT1206307B/it active
-
1982
- 1982-06-16 US US06/388,866 patent/US4526786A/en not_active Expired - Fee Related
- 1982-06-16 US US06/388,867 patent/US4413001A/en not_active Expired - Fee Related
- 1982-06-16 US US06/389,136 patent/US4435415A/en not_active Expired - Fee Related
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