RS59399B1 - Antitela protiv cd38 za lečenje multiplog mijeloma - Google Patents

Antitela protiv cd38 za lečenje multiplog mijeloma

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Publication number
RS59399B1
RS59399B1 RSP20191301A RS59399B1 RS 59399 B1 RS59399 B1 RS 59399B1 RS P20191301 A RSP20191301 A RS P20191301A RS 59399 B1 RS59399 B1 RS 59399B1
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Serbia
Prior art keywords
formula
compound
process according
och3
aryl
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English (en)
Inventor
Weers Michel De
Yvo Graus
Judith Oprins
Paul Parren
De Winkel Jan Van
Vugt Martine Van
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Genmab As
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=36617365&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=RS59399(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Genmab As filed Critical Genmab As
Publication of RS59399B1 publication Critical patent/RS59399B1/sr

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Description

POSTUPAK I INTERMEDIJARI ZA POBIJANJE INHIBITORA
5- LIPOKSIGENAZE
Osnova pronalaska
Ovaj pronalazak se odnosi na postupak i intermedijare za dobijanje inhibitora 5-lipoksigenaze. Inhibitori 5-lipoksigenaze koji se dobijaju shodno ovom pronalasku izloženi su u SAD Patentnoj prijavi serijski br. 09/020,0140 koja je nastavak prijave br. 08/809,901 podnete 13. Juna 1997, od koje se sada odustalo. Ova (pending) prijava koja je pod haslovom inhibitori 5-lipoksigenaze je ovde uključena u svojoj celosti kao referenca.
Inhibitori 5-lipbksigenaze koji se dobijaju shodno ovom pronalasku su selektivni inhibitori aktivnosti enzima lipoksigenaze i korisni su u tretmanu ili ublažavanju inflamatornih bolesti, alergije i kardiovaskularnih bolesti kod sisara.
Kratak sadržaj pronalaska
Ovaj pronalazak se odnosi na postupak za dobijanje jedinjenja Formule
Pri čemu A je CVCsalkil, aril, koji je mono ili disupstituiran sa F, Cl, Br, OCH3, C^Csalkil ili benzil, a koji obuhvata reagovanje jedinjenja Formule
Pri čemu A je C^Csalkil, aril, koji je mono ili disupstituiran sa F, Cl, Br, OCH3, CrC3alkil ili benzil, sa sulfo kiselinom u C^Csalkil alkoholu; i taloženjem jedinjenja Formule I dodavanjem nekog organskog rastvarača koji je manje polaran od alkohola.
Kiselina je metansulfo kiselina a organski rastvarač je diizopropil eter ili etil acetat.
U narednom aspektu ovog pronalaska jedinjenje Formule II se dobija reakcijom jedinjenja Formule
Pri čemu A je CrC6alkil, aril, koji je mono ili disupstituiran sa F, Cl, Br, OCH3, CrCaalkil ili benzil, sa hidroksidom u nekom alkoholnom rastvaraču.
Hidroksid je kalijum hidroksid, a alakohol je tercijerni butil alkohol.
U narednom aspektu ovog pronalaska jedinjenje Formule III se dobija reakcijom jedinjenja Formule
Pri čemu X je Cl, Br ili I sa viškom 4-amin-tiofenol sa bazom u nekom inertnom rastvaraču da bi se dobilo jedinjenje Formule
I daljim tretiranjem jedinjenja Formule VII acilacijom sa nekim kiselim halidom ili anhidridom.
Drugi još poželjniji način dobijanja jedinjenja Formule VI je reakcijom jedinjenja Formule VIII
Pri čemu X je Cl, Br ili I sa viškom 4-amid-tiofenol sa bazom u nekom inertnom rastvaraču.
Pri čemu A je C^Cealkil, aril, koji je mono ili disupstituiran sa F, Cl, Br, OCH3, C^Caalkil ili benzil, sa organskom ili mineralnom kiselinom.
Kiselina je sirćetna, sumporna, mravlja ili p-toluensulfo kiselina. Preferirana kiselina je mravlja.
U narednom aspektu ovog pronalaska jedinjenje Formule IV se dobija reakcijom jedinjenja Formule
Pri čemu A je CrCsalkil, aril, koji je mono ili disupstituiran sa F, Cl, Br, OCH3, CrCaalkil ili benzil, i pri čemu X je Cl, Br, I, ili OCH3sa viškom amino acetaldehid acetala.
Amino acetalaldehid acetal je aminoacetalaldehid dimetilacetal ili aminoacetalaldehid deietil acetal.
U narednom aspektu ovog pronalaska jedinjenje Formule V, pri čemu X je Cl, Br ili I je dobijeno reakcijom jedinjenja Formule
Pri čemu A je C^Csalkil, aril, koji je mono ili disupstituiran sa F, Cl, Br, OCH3, C^Csalkil ili benzil, sa fosfornim pentahalidom u nekom inertnom rastvaraču. Jedinjenje Formule V može takodje da bude dobijeno reakcijom jedinjenja Formule VI sa(CH3)30<*>BF4da formira intermedijar gde x je OCH3.
Pentahalid je fosforni pentahlorid, fosforni pentajodid ili fosforni pentabromid, a rastvarač je toluen. Preferirani A je CH3.
U narednom aspektu ovog pronalaska jedinjenje Formule VI, se dobija reakcijom jedinjenja Formule 4-amid-tiofenol je 4-acetamid-tiofenol. Rastvarač je NMP ili DMSO.
Baza je natrijum karbonat / cezijum karbonat.
U narednom aspektu ovog pronalaska jedinjenje Formule VIII, može biti dobijeno reakcijom jedinjenja Formule
Pri čemu X je Br, Cl ili I sa bis-2-hloretil etrom, nekom alkalnom bazom i faznim transfer katalizatorom u nekom inertnom rastvaraču.
Fazni transfer katalizator je tetrabutil amonijum hidrogen sulfat. Baza je natrijum hidroksid.
Inertni rastvarač je smeša tetrahidrofurana i vode.
Pronalazak se takodje odnosi na novo jedinjenje Formule
Pronalazak se takodje odnosi na novo jedinjenje Formule
Pri čemu A je CrC6alkil, aril, koji je mono ili disupstituiran sa F, Cl, Br, OCH3, CrC3alkil ili benzil.
Pronalazak se takodje odnosi na novo jedinjenje Formule
Pri čemu A je C^C^IkN, aril, koji je mono ili disupstituiran sa F, Cl, Br, OCH3, CrC3alkil ili benzil i pri čemu X je I, Br, Cl ili OCH3.
Pronalazak se takodje odnosi na novo jedinjenje Formule
Pri čemu A je CrC6alkil, aril, koji je mono ili disupstituiran sa F, Cl, Br, OCH3, C1-C3alkil ili benzil i pri čemu R je C^Cgalkil.
Pronalazak se takodje odnosi na novo jedinjenje Formule
Pri čemu A je CVC^alkil, aril, koji je mono ili disupstituiran sa F, Cl, Br, OCH3, CrCgalkil ili benzil.
Preferirano jedinjenje je
Ova nova jedinjenja se koriste u dobijanju inhibitora 5-lipoksigenaze i njihovih farmaceutskih sastava korisnih u tretmanu ili olakšavanju inflamatornih bolesti, alergije i kardiovaskularnih bolesti kod sisara.
Detaljan opis pronalaska
Nov^ postupak sinteze je prikazan niže u Shemi reakcije I
3-bromfenil acetonitril u tetrahidrofuranu je tretiran sa razvodnjenom NaOH, tetra butil amonijum hidrogen sulfatom i bis-2-hlor-etil etrom da bi se dobio aril bromid jedinjenje Formule VIII.
Arilbromid jedinjenje VIII je tretiran bilo sa 4-amintiofenol da bi se dobilo anilin jedinjenje VII čemu sledi acilacija ili sa 4-amidtiofenil da bi se dobilo amid jedinjenje VI. Imidazol funkcija je inkorporirana transformacijom amidogrupe formule VI grejanjem jedinjenja VI sa fosfornim pentahalidom da bi se dobilo jedinjenje V koje je tretirano sa aminacetaldehid alkil acetalom dajući amidin jedinjenje IV. Amidin jedinjenje IV egzistira kao smeša tautomera koji nisu izolovani i koji su odmah izloženi ciklizaciji izazvanoj kiselinom da bi se dobilo imidazol jedinjenje III. Naknadna hidroliza nitril funkcije imidazol jedinjenja III daje inhibitor 5-lipoksigenaze jedinjenja II. Preferirani slani oblik je pronadjena tretiranjem jedinjenja II sa metansulfo kiselinom da bi se dobilo jedinjenje I.
Novi proces iz ovog pronalaska eliminiše prethodne dve skupe reakcije paladijum (O) kuplovanja predstavljajući sulfidno vezivanje za molekul kao što je opisano u. SAD patentnoj prijavi 09/020,0140. koja je ovde u svojoj celosti uključena kao" referenca. Pored toga, gore navedeni i poželjni atom sumpora je prethodno uveden posredstvom TIPS-tiol reagensa (TIPS je triizopropil silil), koji je dobijen iz toksičnog hidrogen sulfida i skupog TIPS-hlorida.
Jedinjenje I gde A je CH3je preferirana slana forma inhibitora 5-lipoksigenaze korisnih u tretmanu ili olakšavanju inflamatornih bolesti, alergije i kardiovaskularnih bolesti kod sisara. Jedinjenje I je posebno korisno u tretmanu ili olakšavanju inflamatornih bolesti.
Ovi korisni inhibitori 5-lipoksigenaze mogu da budu davani u širokom nizu obliku doza.
Za tretman različitih gore opisanih stanja jedinjenja i njihove farmaceutski prihvatljive soli mogu da budu davane čoveku bilo sama, ili - što je poželjnije- u kombinaciji sa farmaceutski prihvatljivim nosiocima ili ražblaživačima u farmaceutskom sastavu shodno standardnoj farmaceutskoj praksi. Jedinjenja mogu da budu davana na konvencionalan način oralno ili parenteralno. -'--.->
Kada se jedinjenja daju čoveku radi prevencije ili lečenja neke inflamatorne bolesti, raspon oralne doze bi bio od oko 0.1 do 10mg/kg telesne težine pacijenta koji se tretira, dnevno, poželjno od oko 0.1 do 4mg/kg dnevno u jednoj ili podeljenim dozama. Ukoliko je poželjno parenteralno davanje, tada bi efektivna doza bila od oko 0.05 do 5mg/kg telesne težine pacijenta koji se tretira, dnevno. U nekim slučajevima može da bude neophodno da se primene doze izvan tih limita pošto doziranje nezaobilazno varira u zavisnosti od starosti, težine i individualnog reagovanja pacijenata, kao i od oštrine simptoma kod pacijenta, te od potencije pojedinačnog jedinjenja koje se daje.
Za oralno davanje, jedinjenja iz ovog pronalaska i njihove farmaceutski prihvatljive soli mogu, primera radi, da budu davana u obliku tableta, praškova, pilula, sirupa ili kapsula, ili kao razvodnjeni rastvor ili suspenzija. U slučaju tableta za oralnu primenu, medju obično korišćenim nosiocima su laktoza i kukuruzni škrob. Dalje,, obično se dodaju i lubrifikacioni agensi, kao što je magnezijum stearal. Kod kapsula -su karisni razredjivači laktoza ili osušeni kukuruzni škrob. Kada su potrebne razvodnjene suspenzije za oralnu primenu, tada je aktivni sastojak pomešan sa agensima emulzifikacije i suspenzije. Ukoliko se želi, mogu se dodati odredjeni agensi ukusa i/ili zaskadjenja. Za intramuskularno, intraperitonealno, podkožno i intravenozno korišćenje obično se pripreme sterilni rastvori aktivnog sastojka, a pH rastvora treba da bude prilagodjen i puferiran. Za intravenozno korišćenje treba da bude kontrolisana totalna koncentracija rastvora kako bi bio izotonski.
Pored toga, posebno za tretman astme, jedinjenja Formule I iz ovog pronalaska mogu biti data pacijentu i inhalacijom. U tom cilju mogu biti davana kao sprej ili kapljičasto shodno standarnoj praksi.
Ovaj pronalazak je islutrovan primerima datim u nastavku, aili nije ograničen njihovim detaljima.
Primer I
4-(3-brom-fenil)-tetrahidro-piran-4-karbonitril
3-bromfenilacetonitril (51 g) u THF (300ml_) je tretiran sa 14% razvodnjenom NaOH (470ml_), tetrabutilamonijum hidrogen sulfatu (9g) i kapanjem dodavanim bis-2-hloretiletrom (32ml_). Reakciona smeša je pod refluksom grejana 4 sata i zatim ohladjena. Smeša je razblažena sa EtOAc (400mL), isprana sa 5% HCI (200mL), vodom (200mL) i zasićenim NaHC03. Posle sušenja preko Mg2S04odstranjen je rastvarač da bi se dobio sirovi CP-399,554 kao voskasta čvrsta supstanca (75,4g). Masa je razmuljena u smešu 1:1 izopropil etra i heksana (100ml_) i dobijeno je 4-(3-brom-fenil)-tetrahidro-piran-4-karbonitril (55,3g, prinos 85%). Primer II 4-[3-(4-amin-fenil-sulfanil)-fenil]-tetrahidro-piran-4-karbonitril 4-(3-brom-fenil)-tetrahidro-piran-4-karbonitril (133.4g), Na2C03(363.6g), CS2C03(223.1 g) i amintiofenol (62.8g) su grejani 24 sata u N-metil-pirolidinonu (2.3L) na 130°C. Dodato je još amintiofenola (35.6g) i grejanje je nastavljeno još 8 sati. Smeša je ohladjena do sobne temperature, sipana na ledenu vodu (6.8L) i filtrirana je. Proizvod je suspendovan u vodi (2.5L), ponovo filtriran i ispran vodom (1.5L). Zatim je proizvod razmuljen u EtOH (0.5L), filtriran i osušen na 40°C / 20mbar dajući 4-[3-(4-amin-fenil-sulfanil)-fenil]-tetrahidro-piran-4-karbonitril (134.3g, 86%). Primer III N-{4-[3-(4-cijan-tetrahidro-piran-4-il)-fenil-sulfanil]-fenil}acetamid 4-(3-brom-fenil)-tetrahidro-piran-4-karbonitril (1.33g), je mešan sa Na2C03(1.59g), CS2C03(0.651 g) i 4-acetamidtiofenol (1g) u N-metil-pirolidinonu (15mL). Reakciona smeša je grejana preko noći na 130°C. Posle hladjenja, smeša je sipana na ledenu vodu. Proizvod se nataložio kao čvrsta masa i prikupljen je usisavanjem uz filtriranje. Čvrsta masa je rekristalizovana iz smeše EtOAc i heksana dajući N-{4-[3-(4-cijan-tetrahidro-piran-4-il)-fenil-sulfanil]-fenil}acetamid (1.4g, prinos 80%). Primeri II i III - kombinovano N-{4-[3-(4-cijan-tetrahidro-piran-4-il)-fenil-sulfanil]-fenil}acetamid
4-[3-(4-amin-fenil-sulfanil)-fenil]-tetrahidro-piran-karbonitril (93.57g) i Et3N (53.1 mL) su rastvoreni u EtOAc (1.23L) i grejani na 50-60°C. U ovaj rastvor je tokom 30 minuta dodavan acetilhlorid (27.7ml_) u EtOAc (73ml_).
Dobijena suspenzija je filtrirana, a filterski kolač je ispran sa EtOAc (3 x 150mL). Kombinovani EtOAc rastvori su isprani vodom (0.5L), poluzasićenim razvodnjenim Na2C03(2 x 0.5L), vodom (0.5L) i zasićenim razvodnjenim NaCI (0.25L). Organski sastojci-su osušeni sa Na2S04i ispareni na 40°C. Sirovi proizvod je rekristalizovan iz refluksovanog EtOH (0.52L), posle hladjenja, filtriranja i sušenja na 40°C / 20mbara dao je N-{4-[3-(4-cijan-tetrahidro-piran-4-il)-fenil-sulfanil]-fenil}acetamid (55.27g, prinos 52%).
Primer IV
4-{3-[4-(2-metil-imidazol-1-il)-fenil-sulfanil]-fenil}-tetrahidro-piran-4-karbonitril
N-4-[3-(4-amin-fenil-sulfanil)-fenil]-tetrahidro-piran-karbonitril (49.77g) je rastvoren u toluenu (545mL) i grejan do 60°C pod azeotropnim uslovima. Iz ovog rastvora je azeotropirano 20mL rastvarača da bi se odstranila preostala voda. U rastvor je u više porcija dodat je PCI5(35g.). Posle jednosatnog mešanja na 60°C rastvarač je destilovan. Ostatak je ohladjen do 10°C i dodata je smeša Et3N (19.8mL) i aminacetaldehid dimetilacetala (15.2ml_) u EtOAc (500mL). Dobijena suspenzija je mešana 30 minuta na 10°C , a zatim je dodato još EtOAC (150mL). Smeša je isprana vodom (360mL) a potom zasićenim razvodnjenim NaCI (150ml_). Organski sastojci su osušeni sa Na2S04(52g) i ispareni na 50°G.'-'Ostatak je rastvoren u mravljoj kiselini (250mL) i grejan 1 sat do refluksa. Reakciona smeša je koncentrovana na 50°C/100mbar do stanja ulja. Ulje je rastvoreno u 10% razvodnjenoj limunskoj kiselini (400mL) i EtOAC (200ml_). Vodeni sloj je ekstrahovan sa EtOAC (200ml_). PH vodenog sloja je podešen na 9 - 10 sa polu-zasićenim rastvorom K2C03(175ml_), a rastvor je ekstrahovan sa EtOAC (200mL). Ekstrakt je osušen sa Na2S04(48g) i isparen na 50°C / 100mbara dajući posle filtriranja kroz silika podlogu koristeći CH2CI2/ MeOH 10% kao razredjivač, 4-{3-[4-(2-metil-imidazol-il)-fenil-sulfanil]-fenil}-tetrahidro-piran-4-karbonitril (27.6g, ukupan prinos 55%).
Primer V
4-{3-[4-(2-metil-imidazol-1-il)-fenil-sulfanil]-fenil}-tetrahidro-piran-4-amid karboksilne kiseline
4-{3-[4-(2-metil-imidazol-il)-fenil-sulfanil]-fenil}-tetrahidro-piran-4-karbonitril (27.35g,) je rastvoren u t-BuOH (280mL) na 50°C. U rastvor je dodat KOH (12.28g) i smeša je mešana preko noći. Suspenzija je ohladjena do sobne temperature i dodata je voda (180mL). Dobijena suspenzija je filtrirana i filterski kolač je osušen na 50°C dajući 4-{3-[4-(2-metil-imidazol-1-il)-fenil-sulfanil]-fenil}-tetrahidro-piran-4-amid karboksilne kiseline (17.52g, prinos 55%). Primer VI 4-{3-[4-(2-metil-imidazol-1-il)-fenil-sulfanil]-fenil}-tetrahidro-piran-4-metil sulfonat amid karboksilne kiseline
4-{3-[4-(2-metil-imidazol-il)-fenil-sulfanil]-fenil}-tetrahidro-piran-4-amid karboksilne kiseline (5.05g,) je suspendovan u MeOH (39ml_) na sobnoj temperaturi. U suspenziju je dodavana metansulfo kiselina kap po kap dok se
sav materijal nije rastvorio. Dobijeni rastvor je filtrran, a filtrat je ispran sa MeOH (20mL). Kombinovani MeOH rastvori su tretirani sa diizopropiletrom (280ml_) na sobnoj temperaturi., Posle mešanja tokom noći formirali su se kristali koji su prikupljeni filtriranjem i osušeni su na 40°C / 19mbar dajući 4-{ 3-[4-(2-metil-imidazol-1-il)-fenil-sulfanil]-fenil}-tetrahidro-piran-4-metil sulfonat amid karboksilne kiseline (4.85g, prinos 77%).

Claims (30)

1. Postupak za dobijanje jedinjenja Formule Pri čemu A je CrC6alkil, aril, koji je mono ili disupstituiran sa F, Cl, Br, OCH3, ^^alkil ili benzil a koji obuhvata reagovanje jedinjenja Formule Pri čemu A je CrCsalkil, aril, koji je mono ili disupstituiran sa F, Cl, Br, OCH3, CrCsalkil ili benzil, sa sulfo kiselinom u C^C^IkN alkoholu; i b taloženjem jedinjenja Formule I dodavanjem nekog organskog rastvarača koji je manje polaran od alkohola.
2. Postupak u skladu sa Zahtevom 1 gde je kiselina metansulfo kiselina.
3. Postupak u skladu sa Zahtevom 1 gde je organski rastvarač diizopropil eter ili etil acetat.
4. Postupak iz Zahteva 1 gde se navedeno jedinjenje Formule II dobija reakcijom jedinjenja Formule Pri čemu A je C^Cealkil, aril, koji je mono ili disupstituiran sa F, Cl, Br, OCH3, C^Caalkil ili benzil, sa hidroksidom u nekom alkoholnom rastvaraču. -
5. Postupak u skladu sa Zahtevom 4 gde hidroksid je kalijum hidroksid.
6. Postupak u skladu sa Zahtevom 4 gde je alakohol tercijerni butil alkohol.
7. Postupak u skladu sa Zahtevom 4 gde se navedeno jedinjenje Formule III dobija reakcijom jedinjenja Formule Pri čemu A je CrC6alkil, aril, koji je mono ili disupstituiran sa F, Cl, Br, OCH3) C^Caalkil ili benzil, sa organskom ili mineralnom kiselinom.
8. Postupak u skladu sa Zahtevom 7 gde je kiselina sirćetna, sumporna, mravlja ili p-toluensulfo kiselina.
9. Postupak u skladu sa Zahtevom 8 gde je preferirana kiselina mravlja kiselina.
10. Postupak u skladu sa Zahtevom 7 gde se navedeno jedinjenje Formule IV dobija reakcijom jedinjenja Formule Pri čemu A je C^Cealkil, aril, koji je mono ili disupstituiran sa F, Cl, Br, OCH3, C^Cgalkil ili benzil, i pri čemu X je Cl, Br, I, ili OCH3sa viškom amino acetaldehid acetala.
11. Postupak u skladu sa Zahtevom 10 gde amin acetalaldehid acetal je aminacetalaldehid dimetilacetal ili aminoacetalaldehid deietil acetal.
12. Postupak u skladu sa Zahtevom 10 gde se navedeno jedinjenje Formule V, pri čemu X je Cl, Br ili I dobija reakcijom jedinjenja Formule Pri čemu A je CrCealkil, aril, koji je mono ili disupstituiran sa F, Cl, Br, OCH3, C^Csalkil ili benzil, sa fosfornim pentahalidom u nekom inertnom rastvaraču, ili gde X je OCH3u Formuli V sa(CH3)30<*>BF4da formira intermedijar.
13. Postupak u skladu sa Zahtevom 12 gde pentahalid je fosforni pentahlorid, fosforni pentajodid ili fosforni pentabromid i rastvarač je toluen.
14. Postupak u skladu sa Zahtevom 12 gde se navedeno jedinjenje Formule VI dobija reakcijom jedinjenja Formule Pri čemu X je Cl, Br ili I sa viškom 4-amin-tiofenol sa bazom u nekom inertnom rastvaraču dajući jedinjenje Formule<r> I daljim tretiranjem jedinjenja Formule VII acilacijom sa nekim kiselim halidom ili anhidridom.
15. Postupak u skladu sa Zahtevom 14 gde je agent acilacije acetil hlorid.
16. Postupak u skladu sa Zahtevom 12 gde se navedeno jedinjenje VI dobija reakcijom jedinjenja Formule VIII Pri čemu X je Cl, Br ili I sa viškom 4-amid-tiofenol sa bazom u nekom inertnom rastvaraču.
17. Postupak u skladu sa Zahtevom 17 gde 4-amid-tiofenol je 4-acetamid-tiofenol.
18. Postupak u skladu sa Zahtevom 16 gde je baza NMP ili DMSO.
19. Postupak u skladu sa Zahtevom 16 gde je baza natrijum karbonat / cezijum karbonat.
20. Postupak u skladu sa Zahtevom 14 gde je je baza natrijum karbonat / cezijum karbonat.
21. Postupak u skladu sa Zahtevom 14 gde je navedeni rastvarač DMSO ili NMP.
22. Postupak u skladu sa Zahtevom 16 gde jedinjenje Formule VIII može biti dobijeno reakcijom jedinjenja Formule Pri čemu X je Br, Cl ili I sa bis-2-hloretil etrom, nekom alkalnom bazom i faznim transfer katalizatorom u nekom inertnom rastvaraču.
23. Postupak u skladu sa Zahtevom 22 gde je inertni rastvarač smeša tetrahidrofurana i vode, baza je natrijum hidroksid i fazni transfer katalizator je tetrabutil amonijum hidrogen sulfat.
24. Jedinjenje Formule ' '■'
25. Jedinjenje Formule Pri čemu A je (VCealkil, aril, koji je mono ili disupstituiran sa F, Cl, Br, OCH3, C^Caalkil ili benzil.
26. Jedinjenje Formuler Pri čemu A je Ci-C6alkil, aril, koji je mono ili disupstituiran sa F, Cl, Br, OCH3, C^Caalkil ili benzil i pri čemu X je I, Br, Cl ili OCH3.
27. Jedinjenje Formule Pri čemu A je CrCgalkil, aril, koji je mono ili disupstituiran sa F, Cl, Br, OCH3>C^Caalkil ili benzil i pri čemu Ft je C^Csalkil.
28. Jedinjenje Formule • Pri čemu A je CrC6alkil, aril, koji je mono ili disupstituiran sa F, Cl, Br, OCH3, CrC<g>alkil "ili benzil.
29. Jedinjenje Formule
30. Jedinjenje Formule gde X je Br, ili Cl.
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