CS224469B1 - Method of l-/-amino-6,7-dimethoxy-2-quinazolinyl/-4-/2-furoyl/-piperazine in crystallic alpha form-l - Google Patents
Method of l-/-amino-6,7-dimethoxy-2-quinazolinyl/-4-/2-furoyl/-piperazine in crystallic alpha form-l Download PDFInfo
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- CS224469B1 CS224469B1 CS137480A CS137480A CS224469B1 CS 224469 B1 CS224469 B1 CS 224469B1 CS 137480 A CS137480 A CS 137480A CS 137480 A CS137480 A CS 137480A CS 224469 B1 CS224469 B1 CS 224469B1
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- furoyl
- quinazolinyl
- dimethoxy
- amino
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-1- 224 469
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Cnocod n<wiyqeHnH KpHCTanjnnecKoíí ot-φορΜΗ rnjipoxjiopHsa I- ( 4-3μηηο-6,7-flHMeTOKCH-2-XHHa3 ojekhhji) -4- (2-4>ypomi) -mmepa- 3HHa O&iaCTI) ΙΓΡΗΜΘΗΘΗΗΗ H3OdpeTeHHg ΗβοόρβτΘΗΗΘ KacaeTca cnocoda nojiyneHna LpHOTa/DnraecKofioC ~φθρΜϋ OTpOXJIOpH£a I-(4-aMHHO^,7-,WeTOKCH-2-XHHa3OJIH·HHJi)-4-(2-4ypoHJi)-ininepa3iiHa cpopMyjm
WS» - 2 - 224 469
Sto COefíHHeHHe ΜΟΗβΤ ΠρΗΜΘΗΗΤΒΟΗ ftTIH ΗβΗβΗΖΗ ΓΗΠβρΤΟΗΗΗ.oé, -$opMa npejíGTaBjmeT codoS cnenjiajiLHyio rapncTaTunmec-rayio ΜΟΛΗφΗκείΐΗΐο 3τογο coeflHHeHHH, oTjmaaioinyiocH οτηοοζτθηβ-ho HH3K0& rarpocKomraHOCTLio. Ejiaroflapn θτομυ CBoiícTBy,no3BOJLmoineMy dojiee TozHyio flO3zpoBKy 3Ta MojuRjpzKaixHH ocoden-HO npUTOAHa flJLH rajieHOBOK φορΜΟΒΚΗ KapCTBSHHOH φορΜΗ.
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Cjieflywrií HeflocTaTOK θτογο cnocoda 3aKJnonaeTCH b tom,ήτο cupoS rnflpoxjiopnfl I-(4/aíMO-6,7~flHMeTOKOH-2-XKHa-3OJI3íHHJl)“4-(2-4>ypOHJX)-niIIiepa3HHa, IIOJiyHeHHHií KaKHM-JIHdOnyTeM, hq nojiynaioT HenocpeflCTBeHHo b KpHCTajLZBrcecKoiíoS-φορΜθ, a OHHCTKa mflpoxjiopnfla I-(4-aM2H0-6,7-fl2MeT0KC2- 2-~x0Ha3OJiHHKJi)-4-(2-í)ypoiui)-iiiinepa3HHa b jnodoíí KpncTajuiH-qeCKOÍÍ φΟρΜΘ 23-3a ero HJIOXO2 paCTBOpHMOCTH Π0ΗΤ2 BO BcexpaoTBopHTejuix HBjmeTCH οηθηβ fíoporoGToameft·
Cawa no cede floporocTOHman, ho HeodxoflHMaH onncTKa capo-ro rnflpoxjiopíma I-(4-aM2H0-6,7-fl2MeT0KC2-2-xHHa30Ji2H2Ji)~4-(2-$ypoHJi)-ininepa3HHa nyTeM nepeKpncTajumsannn BmnonaeTTOT flOnOJEHHTejIBHUH HeflOCTaTOK, ΗΤΟ B 3aB2C2M0CT2 OT ΒΗ—dpaHHux ycjioBHÉ nacTo HenocpeflCTBeHHo ηθ nonynaxT cL -φρ-My, npesnoHHTaeMyEO ajih TepaneBTHnecKnx nenen. Tax b npmae-pe 3 dd-ps 129 652 onncaBaeTCH, ητο 'J' -<popMa nojiynaeTCH23 ρ —φορΜΗ rHflpOXJIOpHfla I-(4-aMHH0-’6,7~fl2MeT0KCH~2-XHHa30-jEHHHJi)-4--(2-$ypo2Ji)-n2nepa3HHa nyTeM nepeapncTajumsanan H3H3oaM2JiOBoro cnnpTa npn HarpeBaHHH pacTBopa flo II5 °C . HHaodopoT, Kax npHBefleHO b npEMepe 4 τογο se naTeHTa, HarpeBa-ΗΗΘΜ Β3ΒΘ0Η -φ)θρΜΗ rZflpOXJIOpHfla I-(4-aMHHO-6,7-fl0MeTOKCH-2-XHHa3OJi2HHJi)-4-(2-$ypoHJi)-nHHepa3HHa Taxse b 23oaM2JioBOMοππρτβ, oflHaxo rq 130 -132 °G, noJiynaxiT ©t-$opMy.
Bojiee BaroflHaM chocoóom ohhctkh caporo rHflpoxJiopnflaI-( 4-aM2H0-6,7-fl2I4e T0KGH-2~X2Ha3 0JI2H2JI) -4- (2-4>ypO2Jl) -nxnepaBZHa, nojiyneHHoro κηκημ—jmdo nyTeM, ηκτηβΐοη nojiy-ηθηηθ 23 Hero cBodoflHoro οοηοβθηηη, Jierae noflflaxiqerocHonniueHHK) nyreM nepeKp2CTajui23an0H hjih flpyrnM cnocodoM,ηθμ ero rHflpoxjiopnfl.3aTeM rnflpoxjiopnfl mojkho nojiynaTB 23ΟΗΗΙξβΗΗΟΓΟ 0CH0BaH2H B 3THJI0B0M ΟΠΗρΤΘ C paCTBOpOM XJIOpHC-ΤΟΓΟ BOflOpOfla B fl23TH2QB0M ΘφΗρβ B COOTBeTCTB22 C DE-PS22 22 231.
HeflocTaTKOM θτογο cnocoda npo23BOflCTBa ηβ;ιηθτοη to, hto - 4 - 224 469 ΗΘΟόΧΟβΗΜΟ ΟΗΘΗΒ dOJILIHOe KOJUBieOTBO pa.CTBOpHTejLH (ftJIHpacTBopeHHH I εθοοβοη nacTH οοηοβθήηή I~(4-awíH0-6,7-jweTOKCH-2-XHHa3OjmiQíJi)-4-(2^ypoiui)-imiiepaBKHa TpedyeT-ca πρΗΜβρΗΟ 150 BecoBux aacTen qthjiobobo cirapTa) η ητο bθτηχ ycjioBHHX EpncTajunneoKaH -$opMa nmpoxjiopHnaI-(4-aMzno-6,7-jweTOKCH-2-xiffla3OJiHHHji) -4- (2-coypoHJi) -πη-nepasHHa He odpaayeTCH. Tojibko nocjie jxonojiHHTejiBHOH one-paumi, no dd-ps 129 652 nyTeM HarpeBanHH b οππρτθ, oo-flepjsaineM ot 5 jjo 7 aTOMOB yrjiepojxa, mojkho nojiynaTB κρη-CTajumaecKyio cO -góopMy.
KeglB H30ÓP6T6HHH H3odpeTeHne no3BOjraeT npoH3BO,HHTL nucTyio KpHGTajunneoKyx) & -$opMy rnnpoxjiopH.ua I-(4-aMHHO-6,7-jweTOKGH-2-xHHa-3OJiHHKJi)-4-(2-$ypoHJi)-iiHnepa3HHa b cymeoTBeHHo ynpoqeH-HHX yCJIOBHflX, B HaCTHOCTH πρζ 3ΗΗΊΗΤθ;ΐΒΗ0 ÓOJiee HH3KHXTeMnepaTypax h o mchbiiihm KOjnraecTBOM pacTBopHTejieÉ hΤΘΜ OSMÉM C JiyaniHM BHXOflOM OTHOCHTejIBHO OdseMa Η ΒρθΜΘΗΗ.
H3JIO5teHHe OyiHHQCTH H30dp6T6HHH 3ajxaneÉ H3odpeTeHHH HBjweTcn ιιροη3βοαοτβο hhctoh κρη-CTajunnecKOH ot -^opMH rnnpoxjiopHfla I-(4-aMHH0-6,7- jm-MeT0KCH-2-XHHa3OJiHHHJi) -4- (2-čj5yponji) -nznepaBHHa oymeoTBeH-HO ynpOiqeHHHM CHOOOdOM. B ΟΟΟΤΒΘΤΟΤΒΗΗ C HaCTOHUíHM H30dpGTeHH6M ΓΗβρΟΧΛΟρΗΛ I—(4—aMZHQ-β, 7-jweTOKCH-2-x3ffla3OjiHHHJi) -4- (2-^ypozji) -imnepa3H-Ha yse ΗΜΘΙΟΙΙξΗΗΟΗ B JipyrOH KpHCTaJDIHHeOKOSt φορΜθ, ksk p -hjih γ -$opMa, hjih hx rnupaT, aHTHnpaT hjlh oojiLBaT ,nepe-bojvit b KpHOTajuiHHecKyK) c/ -ropMy, nepeMeiuzBan ero β βηλθcycneH3HH npn TeMnepaTypax ot 40 jio 95 °C b jtHMeTHJicyjii>$o~KCHHe, flHMeTHJi^opMawme hjih cMecnx hx .npyr c .ijpyroM hjih oapoMaTHnecKMH yrjieBOflopojiaMH, khk deH30Ji hjih TOJiyoji, rajio- - 5 - 224 469 ΓβΗπροΒΘΗΗΗΜΗ aJiii^aTiríecKMií yrjieBOňopoflaMK, khk xjiοροφορΜmm ^eTupexxjiopHCTUÉ yiuiepo#, κθτοηομκ, kbk aupTOH,προοτΗΜΗ 3$HpaMH, ksk /tfioKcaH, mra cnzpTaMH, cojiep&aiwiiiot 2 ao 4 Q.TOMOB yrjiepo.ua, h οταθλβεη nojiy^eHHyio κριιοταπ-jnnecKyK ch -<x)pMy, npH ζ3βθοτηηχ ycjioBHBX, nocjie oxjiawHHH. B cjiynae πρημθηθηηη CMeoež pacTBop^Tejiefi KowiecTBeHHoeοοοτηοϊιιθηηθ κομποηθητοβ μο&θτ KOJiedaTBCH b nmpoKHX npe-flejiax. OcoóeHHO bhto,hhhmii OKa3araoB CMecH b οοοτηοιπθηη-bx ot 10 : I so I : 10. B 3aBHCHM0CTií ot TeMnepaTypu h npuMeHBeMoro pacTBopHTejiBmra CMecH .pacTBopsTejiefi npeBpameirae b xpHCTajura μο&θτjyiHTLCH OT 3 £0 20 BaGOB.
OnpeflejieHHe MOMOHTa, b κοτορϊώ npaKTHqecira hojihoctliooópa3OBajiaci> KpHGTajunneoKaH cZ* -$opMa rHspoxjiopimaI- (4-aMZHO-6,7-ftHMeTOKCH-2-xHHa3Ojrairaji) -4- (2-^ypomi) -nsnepasEHa b ρθθκιχηοηηοκ ομθοη, upobojbitcb η3βθοτηημηB XHMHH MeTO#aMH, ΗΗΠρίϊΜθρ ΟΠΘΚΤρΟΟΚΟΪΕΓΙΘΟΚΗΜ SCCJiejXOBa-ΗΗβΜ Πρθ0.
ΠΡΗΜΘΡΗ OOymeCTBJíeHHB H30dp6T6HZH B nocjie;íyw[x npHMepax Bcer.ua nojiyqajiacL KpacTajunraecKaaH^opMa na^poxjiopHsa Ι-(4-ημηηο-6,7-.ζβίμθτοκοη-2- xraa3OJiHHHJi)-4-(2-$ypoiui)-iBinepa3iiHa /4/. OnpeflejieiraeCTpyKTypa KpucTajuioB bo Bcex cjiy^aax npoBojpuiocB οπθκτρο-οκοπηήοοκημ HccjiesoBairae npod, eme Bnaaorax ot pacTBopz-tojih, b HH$paKpacHOH odjiacTH. Cyunca/4/npoBojíHJiacL npnTeMEepaTypax οτ 110 flo 120 °G. ípyrae KpHCTajLmnecKHeφορΜΗ rB^pOXJIOpUHa I-(4-aMHH0-6,7-flHMeT0KCI[-2-XHHa30JIH-mui)-4-)2^pypoKJi)-niniepa3ZHa, cjiysamne b npHMepax hcxojí- - 6 - 224 469 hum BemecTBOM, τΒκκβ 3apanee onpeftejuumcB μθτο^ομ HHcppa-KpacHofi cneKTpociconHH. ITpuMep I: Β3βθοβ H3 10 r rnflpoxjiopima I-(4-ar.!HHO-6,7-AHivieTOKCH--2-xHHa3OJDíHHJi)-4-(2-$ypoiui)-iiiinepa3HHá ( o -<popMa) b50 mji flHMeTOcyjiBfóoKCHEa HarpeBajOT jxo 60 °G β τθ^θηηθ7 ^acoB. Hocjie οχλθςήθηκη OTcacuBaiOT, ocaflOK npoMtmaioTaneTOHOM h cyinaT.
Bhxojí: 9 r/1/(90 % TeopeTiraecKoro Buxofla).
HpHMep 2: Αηθλογβήηο npiíMepy I πρόβολητ npeBpameime nmpoxjiopujiaI- (4-θμηηο-6,7-jweTOKCH-2-xifflaBOJiiíHXJi) -4- (2-mypoiUi) -mniepa3HHa (nojniTHApaTHaa $opMa) b flHMeTiuicyjiB$OKcimeb c4 -4>opMy.
HpHMep 3: ÁHajiora^HO npzMepy I HarpeBaraeM MeTaojiaTa rnjipoxjiopHflaI— (4—aMHHO—6,7-jweTOKCH-2-XHHa3OJiHHíUi) -4- (2-$ypozji) -nrniepasHHa b AHMeTiuicyjiLťpoKGHfle #o 90 °C β τθηθηηθ 3 na-cob nojiynaioT -$opMy.
HpHMep 4: Βθβθοβ 10 r raspoxjiopima Ι-(4-3μηηο-6,7-αημθτοκοη-2—XHHa3ojmHHJi)-4-(2-4ypoiDi)-iimiepa3iiHa (aurz^paTHaH φορ-Ma) b 50 mji jweTHJi$opMaMHaa HarpeBajoT rq 60 °C b Tene-ηξθ 7 HacoB, nocjie oxjiajKseHHa oTcacaBajoT, ocajiOK npoM&-BaioT aupTOHOM h cymaT. Βηχολ: 9 r/1/ (90 % TeopeTiraecKoro BHXOfía). - 7 - 224 469 ΠρΗΜθρ 5: AHajiorumio irpHMepy 4 ppohcxoaht npeBpameHHe rimpoxjio-pufla I- (4-aMKHO-6,7-AHMeTOKGH-2-XHHa3OJiHHHJi) -4- (2-$yponji)-nmiepasHHa (-4>opMa) b jwewi$0MaMH#e b ds -$opMy. Πρημθρ 6:
HarpeBaiOT B3BecB 5 r rnjipoxjiopimá I-(4-aMHHO-6,7-flHMe-TOKCH-2-xzHa30jniHiM)-4-(2-$ypoHJi)-iiiínepa3HHa ( p -čoopMa)b cmsch H3 12,5 mji Tojiyojia flo 70 °G b Tenenze 8 zacoB.PeaKiíKOHHym cmgcl οοτηβίηιοτ ctoztb na hozl, 3aTeM ocajiozοτΑθΛΗΏΤ, npoMHBaiOT TOJiyojioM z apeioHOM z cymaT.
Buxofl: 4,7 r/l/(94$ TeopeTZHecKoro BHX0.ua). ΠρζΜβρ 7; AHajiorzzHO npzwepy 6 H3 5 r rzjipoxjiopzAa I-(4-aMHH0-6,7-jíHMeT0KCH-2-xHHa30JizHZJi) -4- (2-φγροιυι) -nznepa3ZHa(aHnpupaTHaH góopMa) b ομθοη Z3 2,5 mji jiHMeTHJicyjiB^KCHsaz22,5 mji TOJiyojia HarpeBaHneM jfo 70 °C b τθζθηζθ 15 zacosnoJiysaiOT 4,7 r/1/(94$ TeopeTzzecKoro Bnxo.ua). ΠρΗΜβρ 8: . nojiyqaeTca Taxon &e pe3yjiLTaT, xax b npzMepax I so 7,eCJIH HCnOJIB3yiOT CMeCL flZMeTZJIGyJII^OKGHJía C MeTZJI$OMaMH-AOZ HJIH CMGCH flHMeTHJICyJLb$OKCHfla ZJIZ flZMeTZJI$OpMaL-IHSa 0apoMaTzzecKHMH yrjieBOflopoflaMH xax deH30Ji hjih TOJiyoji, ra-jioreHZ3HpoBaHHHMS amzroaTZzecKHMH yrmeBOflopoflarxK xax xxo-ροφορΜ ra zeTHpexxjiopzcTuft yrjiepofí, κθτοηβμη khk ape-TOH, npOGTHMS θφζρθΜΖ K3K JpiOKCaH HJIH ΟΠΖρΤθΜΗ, ΟΟΑθρΧθΠξΖμη οτ 2 λο 4 aTOMOB yrmepojia. $OpMyjia Η300ρθΤΘΗΗΗ 224 469
Cnocod nojiynenmi KpHCTajunnecKOM có πφορΜΕί rmiporniopn^aI-/4-aMHHO-6,7-KffivieT0KGH-2-XHHa30JiHHHJi/4-/ 2-/pypoiui/-ic-me-pa3HHa HarpesaHneM raj]poxjiopi5^a-I-/4-aMHHO-6,7~jweTOKCH--2-XHHa3Ojmmui/-4~/2-4)ypoiui/-inniepa3HHa mni ero ira^paTa,mru cojiLBaTa %o dojiee bucokux TewmepaTyp b npucyTCTBHspacTBopHTejm flo iipaKTiraecKH nojmoro odpasoBaHmi KpucTaji-jnnecKOH ού -φορκω, oTjranaioiiíEracH τθμ, ητο yse nweioimrifcH bspyroii KpncTajunnecKo0 φορΜθ, κεκ HanpuMep, β - mra'V -$opMa rmipoxjiopíma I-/4-arraH0-6,7-flHMeT0Kcn-2-xHHa30-jiHHmi/-4-/2^)ypomi/-iranepa3iiH mra nx nmpaT, araraupaT mraccwr&BaT nepeMennroaioT npn TeMnepaTypax ot 40 ao 95 °C bflHMeTmicyjiL$0KCH1ne, jweTmižoMarBW mra CMecnx hx Apyr c.npyroM mra c apOMaTHnecKHMX yrjieBOftopoftaMH khk demoji mraTojiyoji, rajioreHH3npoBaHHuira ajm^aTmiecKHMu ynneBojiopoflaMHKas χποροφορΜ mra neTupexxjiopHCTHS: yrjiepoA, κθτοηθμη khkaijeTOH, npocTHira θφκρεΜΗ Kaic jraokcaH, mra cimpTaira, co-flepsamuMH ot 2βο 4 aTOMOB yrjiepo^a, n, řípu cnynae nociieoxaawHHfí, ~ ’ οταθληιοτ nojiyneimyio KpHCTamranec-Kyro -$opMy rajpoxjiopHfla Ι-/4-3μηηο-6,7-λεμθτοκοη-2-:...-xHHa30jraHmi/-4~/ 2-$ypomi/-iranepa3HHa. * 224 469 AHHOTaiw
KpHCTajunniecKaji -$opMa rHApoxjiopo;a I-/4-aMHH0-6,7-jmr^e-TopKCH-2-XHHa30jiHHo/~4-/2-$ypoo/-iiHnepa3HHa ΜΟίχθτ ólítbnojiyneHa npn noMoiiíH nepeMemHBajDiH, npn TeMnepaTypax ot 40£0 95 °G pce HMeíoineroca b .npyroií κρποταοοθοκοΗ φορΜβ,
KaK HaiipHMep, β - hjihT -epopea rnspooopíma I-/4-aMHH0--6,7-jweTOKCH-2-zHHa3(wiHZJi/-4-/2^ypoo/-nHnepa3HHa rahx ropaT, aaropaT mm cojiBBaT b ňHMeTocyjiL$oKcoe, jm-ΜΘΤκπφοΜθΜΗβθ mra CMecBX hx flpyr C ΛΡΥΓΟΜ OH c apoMaTH—ηθοκημη yivieBOftopojiaMH xaK óeH30Ji ra Tojiyoji, rajioreHH3H-pOBaHHHMH aJDK^aTHHeCKHMH yTJieBOAOpO^aMH KHK XJIOpO$OpM OHΗΘΤΈΐρθΧΧΗΟρΗΟΤίώ yTJiepO#, ΚΘΤ0Η3ΜΗ K3IC aneTOH, npOCTBMHθφπρβΜΞ KaK flHOKCaH, HJIH CHHpTaMH, COftepzaHíHMH OT 2 SO 4aTOMOB yrjiepo.ua 5 h, npw cjiynae nocne oxjiasaeHHH, OT#ejunoT HOjiyHeHHyio KpHCTajuiHHecKyio cb -ajfopMy ropo-xjiopoa I-/4-aMHHO-6,7-AHMeTOKCH-2-XHHa30jiHHo/-4-/2-^)ypo-o/-HHnepa3HHa.
WggWK···" »· 7U
Claims (1)
- 224 469 ic PŘEDMĚT VYNÁLEZU Způsob přípravy krystalické <*?-formy hydrochloridu 1-(4-amino-6,7-dimethoxy-2-chinazolinyl )-4- (2-furoyl )-piperazinuzahříváním hydrochloridu i-(4-amino-6,7-dimethoxy-2-chinazoli-nyl)—4—(2—furoyl)—piperazinu nebo jeho hydrátu nebo sol vátuv přítomnosti rozpouštědla do prakticky úplné tvorby krystálické of-formy, vyznačující se tím, že se v jiné krystalické for-mě, napříkladβ- nebo formě, existující hydrochlorid 1-(4-amino-6,7-dimethoxy-2-chinazolinyl)-4-(2-furoyl)-piperazin ne-bo jeho hydrát, anhydrát nebo solvát míchá při teplotách od 40do 95 °C v dimethyl sul f oxidu, dimethylforaamidu nebo jejichvzájemných směsích nebo směsích a aromatickými uhlovodíky jakoje benzen nebo toluen, halogenovynými alifatickými uhlovodíkyjako je chloroform nebo chlorid uhličitý, ketony jako je ace-ton, ethery jako je dioxan nebo alkoholy obsahujícími 2 až 4atomy uhlíku, popřípadě po ochlazení se oddělí získaná krysta-lická <?ď-forma hydrochloridu 1-(4-amino-6,7-dimethoxy-2-china-zolinyl)-4-(2-furoyl)-piperazinu. Uznáno vynálezem na základě výsledků expertizy, provedené Úřa-dem pro vynálezectví a patentnictví, Berlín, DD
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DD21188479A DD141674B1 (de) | 1979-03-29 | 1979-03-29 | Verfahren zur herstellung der kristallinen alpha-form von 1-(4-amino-6,7-dimethoxy-2-chinazolinyl)-4-(2-furoyl)-piperazin-hydrochlorid |
Publications (1)
Publication Number | Publication Date |
---|---|
CS224469B1 true CS224469B1 (en) | 1984-01-16 |
Family
ID=5517404
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CS137480A CS224469B1 (en) | 1979-03-29 | 1980-02-27 | Method of l-/-amino-6,7-dimethoxy-2-quinazolinyl/-4-/2-furoyl/-piperazine in crystallic alpha form-l |
Country Status (7)
Country | Link |
---|---|
CS (1) | CS224469B1 (cs) |
DD (1) | DD141674B1 (cs) |
HU (1) | HU182796B (cs) |
PL (3) | PL128496B1 (cs) |
RO (3) | RO83455B (cs) |
SU (1) | SU1206277A1 (cs) |
YU (3) | YU41908B (cs) |
-
1979
- 1979-03-29 DD DD21188479A patent/DD141674B1/de unknown
-
1980
- 1980-02-12 YU YU36180A patent/YU41908B/xx unknown
- 1980-02-27 CS CS137480A patent/CS224469B1/cs unknown
- 1980-02-28 SU SU807771089A patent/SU1206277A1/ru active
- 1980-03-26 RO RO105233A patent/RO83455B/ro unknown
- 1980-03-26 RO RO80100627A patent/RO79381A/ro unknown
- 1980-03-26 RO RO105234A patent/RO83442B/ro unknown
- 1980-03-27 PL PL22305180A patent/PL128496B1/pl unknown
- 1980-03-27 PL PL24061180A patent/PL129719B1/pl unknown
- 1980-03-27 PL PL24061080A patent/PL129723B1/pl unknown
- 1980-03-28 HU HU74180A patent/HU182796B/hu unknown
-
1983
- 1983-02-07 YU YU26883A patent/YU42069B/xx unknown
- 1983-02-07 YU YU26783A patent/YU42068B/xx unknown
Also Published As
Publication number | Publication date |
---|---|
YU41908B (en) | 1988-02-29 |
PL129723B1 (en) | 1984-06-30 |
RO83455B (ro) | 1984-02-28 |
YU26883A (en) | 1983-10-31 |
RO83455A (ro) | 1984-02-21 |
YU26783A (en) | 1984-04-30 |
HU182796B (en) | 1984-03-28 |
PL129719B1 (en) | 1984-06-30 |
DD141674A1 (de) | 1980-05-14 |
SU1206277A1 (ru) | 1986-01-23 |
DD141674B1 (de) | 1982-06-30 |
YU36180A (en) | 1983-06-30 |
YU42069B (en) | 1988-04-30 |
YU42068B (en) | 1988-04-30 |
PL128496B1 (en) | 1984-01-31 |
RO79381A (ro) | 1982-06-25 |
PL223051A1 (cs) | 1980-12-15 |
RO83442B (ro) | 1984-02-28 |
RO83442A (ro) | 1984-02-21 |
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