PL120037B1 - Process for preparing novel 6-ketodecahydroquinolines - Google Patents
Process for preparing novel 6-ketodecahydroquinolines Download PDFInfo
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- PL120037B1 PL120037B1 PL1979225532A PL22553279A PL120037B1 PL 120037 B1 PL120037 B1 PL 120037B1 PL 1979225532 A PL1979225532 A PL 1979225532A PL 22553279 A PL22553279 A PL 22553279A PL 120037 B1 PL120037 B1 PL 120037B1
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Classifications
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- 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
- C07D215/16—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 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- 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
- C07D215/16—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 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
- C07D215/20—Oxygen atoms
-
- 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
- C07D215/16—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 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Description
Opis patentowy opublikowano: 25.10.1983 120037 C- i ; l-LNIA Urzedu Patentowego Nitkuj IziczTiupoliiij Ludni) Int. CU C07D 215/20 Twórca wynalazku: Uprawniony z patentu: Eli Lilly and Company, Indianapolis (Stany Zjednoczone Ameryki) Sposób wytwarzania nowych 6-ketodehahydrochinolin Pnzedttniofcem wynalazku jest sposób wytwarza¬ nia nowych 6-ketodekahydrochinoiin o ogólnymi Wzorze 1, w którym R oznacza, girape alkilowa o 1—3 atomach wegla1, grape alkilowa lub grujpe benzylowa a R1 oznacza grupe o wzorze COOZ', gidlzie Z' oznacza grupe alkilowa o 1—&' aitomiach wegla luib grupe alkilowa o 1—(2 atoniach wegla pod/stawiona grupa fenyiowa.Sposób wedlug wynalazku polega na tym, ze zwiazek o ogólnym wzoirze 2, w (którym R i Z' maja wyzej podane znacizenie, poddaje sie reak¬ cji z chlorowodorkiem pitydyny i tjrójiffletókieim chromu. Zwiazki o Wzorze 2. sa nowe.Okreislemie „grapa alkilowa o 1—12 atomach we¬ gla" oznacza grupe metylowa i etylowa a oikreisle- nie „grapa alkilowa o 1—3 atomach wegla" obej¬ muje równiez grupe ptopylowa i izcpiropylowa.Zwiazki o wzorze 1 wytwarza sie postepujac jak przedstawiono na schemacie. Spoisób postepo¬ wania opisano na przykladzie tyfllko pojedynczego steroizomeru (odnosnie steireochemii mostka we¬ glowego) — izomeru 4a^, 8act. Na schemacie Z<— —CO jest acylowa grupa ochronna, gcMe Z o- znacza grupe alkilowa o 1—3 atomach wejgfla, gru¬ pe alkenyiowa o 2-^3 atomach wegla,, grupe alfci- nylowa o 2—J3 atomach wegla, grupe cykloalkilo- wa o 5—6 atomach wegla, grupe fenyiowa lub podisitawicma grupe fenyiowa, przy czym podlsitaw- nlikiem moze byc grupa metylowa, metotasylowa, 10 15 20 25 30 atom chloru i tym poidobnie w dowolnym polo¬ zeniu pierscienia fenylowego. Grape Z—CO moze stanowic, przykladowo, grupa acetylowa, propio- nylowa*, butyrylowa, proctiolilowa, akryilililowa, benzoilowa, p-tolksilowia, o^chloirobenzoilowa, m- -nietokisymlbenzodiowia i tym podobne.Zgodnie zie schematem, 4^acyloikByHcyMoheksa- non o wzorze 3 poddaje sie reakcji z asitrem a- -chlorowcometyloakrylanowym, przykladowo estrem etylowym i amina o wzorze RNH2, gdzie R ozna¬ cza g*rape alkilowa o 1^3 atomach wegla, girupe allilowa lub grupe benzylowa.Produktem tej reakcji jest mttesza(nina DL-1- ^dlstawionej-3-eitolksykar^ 5,6,7,8-ofctahydlrochinoliny i DL-il-podstawionej-HA 3,4,'4a,5^97-ok1ahydlrochlinoliny o wzorze 4, w kltó- rym kropkowana' linia oznacza alternatywne po¬ lozenie podwójnych wiazan. Otrzymane izomery przeksztalca- sie w sole chlorowodorkowe a ich mieszanine redlukuje sie cyjanoborowodorkiem so¬ dowym otrzymujac trans-DL-l^podisitawlona-B-eito- ksykanbonylo^6iacyloksydekahydlrochinoline o wzo¬ rze 5.. W wyniku hydrolizy tego dwueistnu otrzymuje sie kwas 6nhyidlroklsyr3-Jkarfooksylowy a nastepnie przez reetstryfikacje kwasowej grupy karboksylo¬ wej etanolem otrzymuje sie tranis-iDL-il-poidlstawiona-SHetoiksy- karbonylo-6-hydlroiklsyH^kahydliochkioline o wzorze 120 037120 037 3 4 sadlke ekstrakcyjna Soxleta wypelniona sitami molekularnymi typu 3A. Mieszanine reaikcyljna o- chlodizono, rozcienczono wodnym roztworom wo¬ doroweglLaiiu sodowego i alkaliczna mieszanine 5 ekstrahowano kilkakrotnie chloroformem. Eks¬ trakty chloroformowe polaczono i przemyto nasy¬ conym wodnymi roztworem chlorku sodu i suszo¬ no. Po oid|pedizeniu chlorotformiu otrzymano 10,3 g pozostalosci zawierajacej trans 10 toksyfearbonylo^-hydirolksydekianydrochinolme wy¬ tworzona w powyzszej hydrolizie po chromatografii na 150 g preparatu florisil z uzycieim chlorofor¬ mu zawierajacego zwiekszajace sie (£—10!%) ilosci metanolu jako eluenta. 15 Przygotowano rozitwor z 8,8 g transHDL-\l-(pto- pylo-B-e;to(ksyikarbonydo-6-hydlroiksyicyekahyidlrochi- noliny i 4O0 ml dwuchloirometylaniu i podano don 4,1 g octanu sodowego. Nastepnie dodano 10,8 g odczynnika chlorowodorek pirydyny, trójtlenek 20 chromu i otrzymana mlieszanine mieszano w ciagu okolo 22 godzin, po czym przesaczono i przesacz zatezono pod piróznia. Oitrzymany koncentrat roz¬ puszczono w chloroformie a roztwór chloroformo- wy poddano chromatografii na 150 g preparatu florisil z. uzyciem chloroformu zawierajacego zwiejkszajace sie .(1—12%) iloisici metanolu jako e- luenta. Metoda chromatografii ciemkowarstwowej stwierdzono, ze frakcje zawieraja trans-DL-il-pro- pylo-S-etoksyikairtoonylo-G-lketoideikahydrochinoline.Charakterystyka produktu /Izwiiazek trans o, wzo¬ rze 1, w którym R=n^CaH7 a R1=COOC2H5/ Widmo IR/CHay 1715 -cm-1 keton C=0 17i25 cm-1 ester G=0 Widdno NMR '/GOdJ /\W JYEHz/ . 53 cykle/s, triplet, N^CH2^CH2—CH3 77 cykli/ls, triplet, —O—CH2—CH3 250 cykli/s, kwartet, —O^CH2—-CH3 2. Utleniajac grupe hydroksylowa odczynnikiem • Saretta (chlorowodorek pirydyny i trójltlenek chromoi) otrzymuje sie odpowiedni nowy 6-keto zwliazelk o Wzorze 1.Zwiazki o wzorze 1 stanowia produkty posred¬ nie do wytwarzania nowych oktanydropirazolo[3,4- ig]chinolin, .które isa przydatne jaJko srodki lecz¬ nicze o dzialaniu agonistycznyrn wzgledem dopa- miny.Przyikilatd Mieszanine 10 ml propyloamfiny i 400 ml toluenu ochlodzono w mieszaninie wody z liodieni. Dodano do niej po kropli roztwór 16,5 g a-^bromometyloi/aikrylanu etylu..Otrzymana imlieszanine mieszano i chlodzono w ciagu okolo 25 mliniut. Nafstejpnie do.dlano po- kropli roztwór 11 g 4-lhenzoilloksycyklo-ihe'ksanonu w 75 ml toluenu. Te nowa mlieszanine ogtrzewano w temperaturze wrzenia pod chloidnica zwrotna w atmosferze azotu w ciagiu 213 godzin. Chlodnice zwrotna wyposazono w nasadke ekstrakcyjna Soxleta wypelniona sitami molekularnymi typu 5A w celu usuniecia wody. ¦Naistejpinlie mieszanine reakcyjna oichlodzono i przesaczono. W pozosta¬ losci {po odpedzaniu rozpuszczalników znajdowaly sie l-propylo-3-etoiklsyika^bonylo-6-lbenzoilolksy^l,2, 3,4,5,6,7,8K)k)tahydTochmolina ora-z .l-pa:opylo-3^eto- klsyikairibonylo-6-ibenzoiloiksy-il,2(^3,4,4a,i5,6,,7-olktahy- drochinolina.Pozostalosc te rozpuszczono w mieszaninie eter— chloroform i otrzymany rozfe^ór... nasycono gazo¬ wym chlorowodorem przy jednoczesnym utrzymy¬ waniu temperatury reakcji w granicach 0—5°C.Rozpuszczalnik zdekanltowano znaid krysztalów chlorowodorków tak otrzymanych. Ohlorowodbirlkji rozpuszczono w 100 ml metanolu, dodano 300 ml THF i koncowy rozitfwóirocliiojdlzono w mieszani¬ nie wody z lodem. Podczas miLeseania i ochladza¬ nia dodano nastepnie porcjami 15.sg wodoir'ku sodowego, po.czyim miesaanane reaikcyj^ na mieszano ptzez dalsze ly2l5 £odlzftny i rozcien^ czono nastepnie woidlnym roztworem weglanu so¬ dowego. , •.. .Wodina alkaliczna mieszanine eksibrajaowano da^ lej kilkakrotnie octanem etylu, ekstrakty poiaczo-.. no i przemyto nasyconym . wodnym < roztworem chlorku sodu i suszono. Po odpedzeniu rozpusz- czalniika otrzymano trans-DLnl^ropylo-G^01^ lrarbonylor^-lbenizoilofesy^ Zwiazek ten trozpmszic^ono w m&eszan^nje 400.,ml metanolu i 100 ml 2N wodoejgo rozporu wodo¬ rotlenku sodowego, mieszano -w temtperat^i^zie .po¬ kojowej w atmosferze azotu w ,. c iajgia -6^4 godzin i po tym czasie lotne substancje usunieto .przez oidjparowanie pod próznia., .Otrzymana, pozostalosc rozproszono w 800 ml etanole i li5 ml 1 2N wodL nego roztworu kwasu, sokiego. ; : Mieszanine estryfikacyjna ogrzewano w tempe¬ raturze wrzenjia pod chlodnica. zawrotna i odde¬ stylowano- okolo 300 ml rozpuszczalnika. Dodano nastepnie dalsze 300 ml etanofllu i mieszanine re- aikcyjna ogrzewano w temperaturze wrzenia w ciagu 26 godlzin w aparaturze wyposazonej w na- PL PL
Claims (2)
1. Zastrzezenia patentowe 1.. Sposób wytwarzania nowych 6-ketodlekahy- drochinolin o ogóllnym wzomze 1, w którym R o- znacza grupe alkilowa o 1—3 atomach wegla, gru¬ pe alljilowa lufo grupe benzylowa a R1 oznacza grupe o wzorze OOOZ', gdzie Z' oznacza grupe etylowa, znamienny tym, ze. zwiazek o .ogóHnym wzorze 2, w którym R i Z^maija wyzej podane . znaczenie, poddaje sie reakcjd z chlorowodorkiem pirydyny i trójtlenkiem chromu.
2. Sposób wytwarzania nowych 6-ketodekiahy- ójrochinolin o ogólnym wzorze 1, w którym R o- znacza grupe alkilowa o 1—3 atoiraach wegla, gru¬ pe allilowa lub grupe benzylowa a R1 oznacza grupe o wzorze COOZ', gdzie Z' oznacza .grupie metylowa lub grupe alkilowa o 1—/2 atomach we^ gla poidistawioina girupa fenylowa, znajmieminy tym, ze zwiazek o ogólnym wzorze 2, w którym R i Z' maja wyizej podane znaczenie, ,poddaije Sie reakcji z chlorowodorkiem pirydyny i tróijtlenlkiem chro¬ mu, 10 15 20 25 30 35 40 45 50 55 •120 037 o RNH, Wzór 3 o-co-z HC^S^COOZ' Wzór 2 l N CH2=C-COOZ' CH2 Hal _0H" JtpJH HCl pirydyna • HCl Cr03 °€DCWZ' R Wzór 1 Schemat 7 Wzór 4 _ CO K COOZ' kwasBH; Wzór 5 & Wzór 1 HO- H R COOZ' PL PL
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US506179A | 1979-01-22 | 1979-01-22 | |
| US06/031,641 US4198415A (en) | 1979-01-22 | 1979-04-19 | Prolactin inhibiting octahydro pyrazolo[3,4-g]quinolines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL120037B1 true PL120037B1 (en) | 1982-02-27 |
Family
ID=26673868
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1979225532A PL120037B1 (en) | 1979-01-22 | 1979-06-29 | Process for preparing novel 6-ketodecahydroquinolines |
| PL1979225531A PL119715B1 (en) | 1979-01-22 | 1979-06-29 | Process for preparing novel 6-keto-7-dimethylaminomethylen-decahydroquinolinesekagidrokhinolinov |
| PL1979225533A PL119785B1 (en) | 1979-01-22 | 1979-06-29 | Method of manufacture of novel 6-hydroxydecahydroquinolines |
| PL1979216719A PL122153B1 (en) | 1979-01-22 | 1979-06-29 | Process for preparing novel octahydropyrazolo-/3,4-g/ quinolinesnov |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1979225531A PL119715B1 (en) | 1979-01-22 | 1979-06-29 | Process for preparing novel 6-keto-7-dimethylaminomethylen-decahydroquinolinesekagidrokhinolinov |
| PL1979225533A PL119785B1 (en) | 1979-01-22 | 1979-06-29 | Method of manufacture of novel 6-hydroxydecahydroquinolines |
| PL1979216719A PL122153B1 (en) | 1979-01-22 | 1979-06-29 | Process for preparing novel octahydropyrazolo-/3,4-g/ quinolinesnov |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4198415A (pl) |
| EP (2) | EP0013787B1 (pl) |
| AT (1) | AT371819B (pl) |
| AU (1) | AU528076B2 (pl) |
| CA (1) | CA1136140A (pl) |
| CH (3) | CH644377A5 (pl) |
| DD (5) | DD148340A5 (pl) |
| DE (2) | DE2966951D1 (pl) |
| DK (1) | DK268879A (pl) |
| EG (1) | EG14696A (pl) |
| ES (4) | ES482089A1 (pl) |
| FI (1) | FI65247C (pl) |
| FR (5) | FR2446832A1 (pl) |
| GB (4) | GB2040915B (pl) |
| GR (1) | GR72516B (pl) |
| IE (1) | IE48394B1 (pl) |
| IL (1) | IL57668A (pl) |
| LU (1) | LU81439A1 (pl) |
| MY (1) | MY8500683A (pl) |
| NZ (2) | NZ201279A (pl) |
| PH (3) | PH14909A (pl) |
| PL (4) | PL120037B1 (pl) |
| PT (1) | PT69829A (pl) |
| RO (2) | RO82159A (pl) |
| ZA (1) | ZA793243B (pl) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL65269A0 (en) * | 1981-03-24 | 1982-05-31 | Lilly Co Eli | 6-substituted hexahydroindazolo or hexahydroisoindolo isoquinolines |
| US4540787A (en) * | 1982-06-03 | 1985-09-10 | Eli Lilly And Company | Method of preparing trans-D1-1-alkyl-6-oxodecahydroquinolines |
| US4468401A (en) * | 1982-11-03 | 1984-08-28 | Eli Lilly And Company | Method of blocking peripheral norepinephrine release |
| US4471121A (en) * | 1982-11-03 | 1984-09-11 | Eli Lilly And Company | Method of resolving trans-d alpha-1-n-propyl-6-oxodecahydroquinoline and di-p-toluoyltartaric acid salts thereof |
| ES524452A0 (es) * | 1982-11-03 | 1985-04-16 | Lilly Co Eli | Un procedimiento para la preparacion de derivados de pirazolo-quinolinas. |
| US4567266A (en) * | 1982-11-03 | 1986-01-28 | Eli Lilly And Company | Method of preparing octahydro-1H(and 2H)-pyrazolo[3,4-g]quinolines |
| US4647667A (en) * | 1982-11-03 | 1987-03-03 | Eli Lilly And Company | Octa- and deca-hydroquinoline intermediates |
| EP0127708B1 (en) * | 1983-06-03 | 1987-09-09 | Eli Lilly And Company | Trans-dl-1-alkyl-6-alkoxyoctahydroquinolines |
| US4626591A (en) * | 1983-08-10 | 1986-12-02 | Eli Lilly And Company | Trans-dl-1-alkyl-6-alkoxy-1,2,3,4,4a,5,8,8a octa-hydroquinolines |
| US4528290A (en) * | 1984-01-30 | 1985-07-09 | Eli Lilly And Company | Stimulating dopamine D-1 receptors |
| US4521421A (en) * | 1983-09-26 | 1985-06-04 | Eli Lilly And Company | Treatment of sexual dysfunction |
| RO89126A (ro) * | 1983-09-26 | 1986-04-30 | Eli Lilly And Co,Us | Procedeu de preparare a unor derivati de chinolina |
| US4507478A (en) * | 1983-09-26 | 1985-03-26 | Eli Lilly And Company | 2-Mercaptopyrimidohexahydroquinolines and related compounds |
| IL73001A0 (en) * | 1983-09-26 | 1984-12-31 | Lilly Co Eli | Improvements in and relating to 6-oxodecahydroquinolines |
| US4501890A (en) * | 1983-09-26 | 1985-02-26 | Eli Lilly And Company | Trans-(±)-2,4,6-substituted-5,5a,6,7,8,9,9a,10-octahydro-pyrimido[4,5-g]quinolines |
| CA1270488A (en) * | 1983-09-26 | 1990-06-19 | John M. Schaus | Pyrazole-ring alkylated pyrazoloquinolines and intermediates |
| US4587351A (en) * | 1984-04-18 | 1986-05-06 | Eli Lilly And Company | Synthesis of ketones with calcium hypochlorite |
| US4689415A (en) * | 1984-04-18 | 1987-08-25 | Eli Lilly And Company | Trans octahydroquinoline intermediate |
| US4537893A (en) * | 1984-04-27 | 1985-08-27 | Eli Lilly And Company | Octahydrothiazolo[4,5-g]quinolines and use as prolactin secretion inhibitors |
| DK349185A (da) * | 1984-08-02 | 1986-02-03 | Lilly Co Eli | Octahydro-oxazolo(4,5-g) quinolin-forbindelser og fremgangsmaade til fremstilling heraf |
| US4600777A (en) * | 1984-08-02 | 1986-07-15 | Eli Lilly And Company | Method of preparing 1-alkyl-7-oxodecahydroquinolines, and cis(±) and tran(±)isomers so prepared |
| HUT40656A (en) * | 1984-08-03 | 1987-01-28 | Lilly Co Eli | Process for producing tricyclic quinoline derivatives |
| US4537964A (en) * | 1984-08-03 | 1985-08-27 | Eli Lilly And Company | Method of preparing permissibly-substituted 1H(and 2H)pyrazolo[3,4-g]quinolines; pyrimido[4,5,g]quinolines; thiazolo[4,5,g]quinolines and intermediates therefore |
| US4537965A (en) * | 1984-08-03 | 1985-08-27 | Eli Lilly And Company | Method of preparing 4aR,8aR-5-permissibly substituted-6-oxo-octahydro-1H(and 2H)-pyrazolo[3,4-g]quinolines, useful as intermediates |
| US4552956A (en) * | 1984-08-15 | 1985-11-12 | Eli Lilly And Company | Partially hydrogenated pyrazolo, pyrimido and thiazolo[1,4]benzoxazines |
| US4587336A (en) * | 1984-08-15 | 1986-05-06 | Eli Lilly And Company | Partially hydrogenated intermediate pyrazolo, pyrimido and thiazolo[1,4]benzoxazines |
| FR2578254B1 (fr) * | 1985-03-01 | 1987-03-06 | Roussel Uclaf | Nouveaux derives de la pyrazolobenzoxazine, leurs sels, procede de preparation, application a titre de medicaments, compositions les renfermant, et des intermediaires |
| US4595754A (en) * | 1985-03-04 | 1986-06-17 | Eli Lilly And Company | Process for preparing cis N-alkylperhydroquinolines |
| US4927828A (en) * | 1985-03-08 | 1990-05-22 | The Trustees Of Princeton University | Diastereoisomeric tetrahydropyrido-(2,3,d) pyrimidine derivatives |
| US4622398A (en) * | 1985-06-24 | 1986-11-11 | Eli Lilly And Company | Dialkylaminotetrahydroquinazoline |
| US4826986A (en) * | 1986-06-16 | 1989-05-02 | Eli Lilly And Company | 6-Oxo-trans-octa- and decahydroquinolines |
| US5134143A (en) * | 1986-06-16 | 1992-07-28 | Eli Lilly And Company | BCD tricyclic ergoline part-structure analogues |
| US4977160A (en) * | 1986-06-16 | 1990-12-11 | Eli Lilly And Company | BCD tricyclic ergoline part-structure analogues |
| US4762843A (en) * | 1986-09-15 | 1988-08-09 | Warner-Lambert Company | Hetero [f] fused carbocyclic pyridines as dopaminergic agents |
| US5057515A (en) * | 1989-07-24 | 1991-10-15 | Eli Lilly And Company | Method for agonizing a dopamine receptor |
| US5006525A (en) * | 1989-07-24 | 1991-04-09 | Eli Lilly And Company | Dopamine agonists method |
| US4977149A (en) * | 1989-07-24 | 1990-12-11 | Eli Lilly And Company | Pyridoquinoline dopamine agonists, compositions and use |
| US4939259A (en) * | 1989-07-24 | 1990-07-03 | Eli Lilly And Company | 2-oxo-pyrido[2,3-g]quinoline derivatives |
| DK0550635T3 (da) * | 1990-09-28 | 1995-09-04 | Pfizer | Cykliske forbindelser med kondeserede ringe, som er analoger til nitrogenholdige ikke-aromatiske het erocykliske forbindelser |
| US5416090A (en) * | 1991-01-31 | 1995-05-16 | Eli Lilly And Company | Method of treating inflammation |
| US20030212085A1 (en) * | 2001-04-17 | 2003-11-13 | Mccall Robert B. | Treatment of fibromyalgia and chronic fatigue syndrome |
| MY148644A (en) * | 2005-07-18 | 2013-05-15 | Orion Corp | New pharmaceutical compounds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3084165A (en) * | 1959-05-21 | 1963-04-02 | Bayer Ag | Quinone derivatives and processes for producing the same |
| US3600393A (en) * | 1969-03-03 | 1971-08-17 | Aldrich Chem Co Inc | Dialkylamino alkylamino pyrazolo (3,4b) quinolines |
| US3859291A (en) * | 1973-10-01 | 1975-01-07 | Morton Norwich Products Inc | 9-(p-anisidino)-7-methyl-(1h)-pyrazolo(3,4-f)quinoline |
| US4028381A (en) * | 1975-05-05 | 1977-06-07 | Ciba-Geigy Corporation | Pyrazolobenzazepines |
-
1979
- 1979-04-19 US US06/031,641 patent/US4198415A/en not_active Expired - Lifetime
- 1979-06-26 IL IL57668A patent/IL57668A/xx unknown
- 1979-06-26 NZ NZ201279A patent/NZ201279A/en unknown
- 1979-06-26 NZ NZ190835A patent/NZ190835A/en unknown
- 1979-06-26 PT PT69829A patent/PT69829A/pt unknown
- 1979-06-26 CA CA000330552A patent/CA1136140A/en not_active Expired
- 1979-06-26 DK DK268879A patent/DK268879A/da not_active Application Discontinuation
- 1979-06-27 RO RO79104044A patent/RO82159A/ro unknown
- 1979-06-27 LU LU81439A patent/LU81439A1/xx unknown
- 1979-06-27 AU AU48445/79A patent/AU528076B2/en not_active Ceased
- 1979-06-27 FR FR7916571A patent/FR2446832A1/fr active Granted
- 1979-06-27 PH PH22704A patent/PH14909A/en unknown
- 1979-06-27 RO RO7997973A patent/RO77563A/ro unknown
- 1979-06-28 GB GB7922530A patent/GB2040915B/en not_active Expired
- 1979-06-28 DE DE7979301250T patent/DE2966951D1/de not_active Expired
- 1979-06-28 AT AT0452479A patent/AT371819B/de not_active IP Right Cessation
- 1979-06-28 DE DE8181110640T patent/DE2966945D1/de not_active Expired
- 1979-06-28 FI FI792046A patent/FI65247C/fi not_active IP Right Cessation
- 1979-06-28 EP EP79301250A patent/EP0013787B1/en not_active Expired
- 1979-06-28 GB GB8203156A patent/GB2092579A/en not_active Withdrawn
- 1979-06-28 GR GR59466A patent/GR72516B/el unknown
- 1979-06-28 GB GB8203157A patent/GB2092580B/en not_active Expired
- 1979-06-28 GB GB8203158A patent/GB2092581A/en not_active Withdrawn
- 1979-06-28 EP EP81110640A patent/EP0050881B1/en not_active Expired
- 1979-06-28 CH CH606079A patent/CH644377A5/fr not_active IP Right Cessation
- 1979-06-29 ES ES482089A patent/ES482089A1/es not_active Expired
- 1979-06-29 PL PL1979225532A patent/PL120037B1/pl unknown
- 1979-06-29 PL PL1979225531A patent/PL119715B1/pl unknown
- 1979-06-29 DD DD79218313A patent/DD148340A5/de unknown
- 1979-06-29 ES ES482091A patent/ES482091A1/es not_active Expired
- 1979-06-29 ES ES482090A patent/ES482090A1/es not_active Expired
- 1979-06-29 DD DD79218311A patent/DD148518A5/de unknown
- 1979-06-29 DD DD79213992A patent/DD144670A5/de unknown
- 1979-06-29 ES ES482087A patent/ES482087A1/es not_active Expired
- 1979-06-29 DD DD79218312A patent/DD148339A5/de unknown
- 1979-06-29 ZA ZA793243A patent/ZA793243B/xx unknown
- 1979-06-29 DD DD79218310A patent/DD148517A5/de unknown
- 1979-06-29 PL PL1979225533A patent/PL119785B1/pl unknown
- 1979-06-29 PL PL1979216719A patent/PL122153B1/pl unknown
- 1979-06-30 EG EG393/79A patent/EG14696A/xx active
- 1979-08-08 IE IE1209/79A patent/IE48394B1/en unknown
- 1979-11-06 FR FR7927309A patent/FR2446821A1/fr not_active Withdrawn
- 1979-11-06 FR FR7927310A patent/FR2446822A1/fr active Granted
- 1979-11-06 FR FR7927311A patent/FR2446820A1/fr active Pending
- 1979-11-06 FR FR7927308A patent/FR2446834A1/fr active Granted
-
1980
- 1980-03-12 PH PH23757A patent/PH14991A/en unknown
- 1980-03-12 PH PH23756A patent/PH14908A/en unknown
-
1983
- 1983-06-20 CH CH336883A patent/CH644365A5/fr not_active IP Right Cessation
- 1983-06-20 CH CH336783A patent/CH644607A5/fr not_active IP Right Cessation
-
1985
- 1985-12-30 MY MY683/85A patent/MY8500683A/xx unknown
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