HUE031390T2 - CB1 receptor antagonisták - Google Patents

CB1 receptor antagonisták Download PDF

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Publication number
HUE031390T2
HUE031390T2 HUE12721545A HUE12721545A HUE031390T2 HU E031390 T2 HUE031390 T2 HU E031390T2 HU E12721545 A HUE12721545 A HU E12721545A HU E12721545 A HUE12721545 A HU E12721545A HU E031390 T2 HUE031390 T2 HU E031390T2
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Hungary
Prior art keywords
pregnenolone
receptor
disorders
substituted
induced
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HUE12721545A
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English (en)
Inventor
Pier Vincenzo Piazza
Monique Vallee
Giovanni Marsicano
François-Xavier Felpin
Luigi Bellocchio
Daniela Cota
Jean-Michel Revest
Sergio Vitiello
Umberto Spampinato
Rafael Maldonado
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Inserm - Inst Nat De La Sante Et De La Rech Medicale
Univ Bordeaux
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Application filed by Inserm - Inst Nat De La Sante Et De La Rech Medicale, Univ Bordeaux filed Critical Inserm - Inst Nat De La Sante Et De La Rech Medicale
Publication of HUE031390T2 publication Critical patent/HUE031390T2/hu

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
    • C07J7/0065—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by an OH group free esterified or etherified
    • C07J7/0075—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by an OH group free esterified or etherified substituted in position 17 alfa
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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    • A—HUMAN NECESSITIES
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
    • C07J13/005—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 16 (17)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
    • C07J13/007—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 17 (20)
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    • C07—ORGANIC CHEMISTRY
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    • C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
    • C07J41/0011—Unsubstituted amino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07J41/0027—Azides
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    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of only two carbon atoms, e.g. pregnane derivatives
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    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • C07J5/0007—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond not substituted in position 17 alfa
    • C07J5/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond not substituted in position 17 alfa not substituted in position 16
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
    • C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
    • C07J7/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
    • C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
    • C07J7/004—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa
    • C07J7/0045—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa not substituted in position 16
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
    • C07J7/0065—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by an OH group free esterified or etherified
    • C07J7/007—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by an OH group free esterified or etherified not substituted in position 17 alfa

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Claims (4)

  1. CB I xaaagtor aotagoaisták hzatytiklow Igkiygootok I , A a alábbiak közül akasztott pregnenolon-svárrnaxék * (lg
    képleíü vegyiket vagy gyógyászatiig elfogadható sója, ahol ~ RÍ azt felérni hogy a €3-hclyzet ΌΗ vagy --G csoporttal szubsztituált, - R2 azt jelenti, hogy a Cl /'helyzet 1Ά szénatumos aiköesopomah haiogénatoráiail vagy Bo'-csoporttal szuhszhukk Ck U aziJelegC'h hogy-a CCO^holyget 43ff vagy ~k csoporttal szuhszntuált, és ™ B.4 gat jel értig hogy aC MBtély tyt 41 aiptpttpti. ii?4ilbs#.i:«41i " (%
    képleia vagy ülőt vagy gyógy aszal húg elfogadható: sója. ahol Pl :azt jelent!, hogy a (kkkyzk -Ν1ίτ; Brs~k>~ vagy -Ma osöportíal aaahaltliaáh, -112 oof jelenti* bogy a Öf-Myxétyfí atomssal szobazótoált, 944 R3 azt jelenti, hogy a CCO-helyzet -:ϊΟ csoporttal szohsEtkuálh % ™ R4 azt jelenti, hogy a Cl Ó-helpet -li aiiorniml sEutrszf linóit vagy 444 R í azt jdeoib hogy a C3'helyzet 1.«8:-S2énMoMo§.-aikhxksnportial, halogdiatoanoah Ö«~ ö- vagy 4¾. csogertla! sanbsEtituáU, · R.2 azt jelenít,, hogy a C l 7 heiyoeot -Bm -Öh vagy 236 szendomos alkenf ksoporhal SEebszhtuáh, 994 ILI. azt jelenti. hogy a OO-helyzet :::0 csoporttal Nzubszthuáh.. és —- 114 azt jelenti, hogy a Ülh-helyzö -H atommal szuhsatituált, vagy 449 Ri Mt jelenti* hogy a C3~hdyzei -Ölt csoptortlal szohaEtúaáh. - R2:azt jelenti, hogy a Cl7-helyzet 1-8 szépdpmos alkik 1 -8 szónöomos alköxl vagy Bii-csoportta! szubsziituáli, - R3 azt jelenti, hogy a Cötl-helyEel -<) csoporttal szufeszlttoálc én. 41™ R4 azt jelenti» hogy a C!6-hdyzei. -B atommal szabsz* imáig vagy --Ο Rí azt jelenti, hogy a C3-hely«et -OH csoporttal szukszthuóih - R2 azt jelenti, hogy a Ct't-helyzei 4! atommal sznbsEtlmlih ™ R3 azt jelenti. hogy a C2CMiefyzet 41, -Öli vagy -NR.8R9 csoporttal szubsztnoált, ahol RB és R9 egymástól függetlenül -H vagy 1-8 szénatornos dkbesöpört, és 444 Mezt jelend, hogy a CIR-helvzet 41 atommal szabs/thnák. vagy '(Ej::
    képieto vegy Ölet v agy gyógyászstlkg effogadható sója. aliek ^ 'RÍ adi jelenti hogy a €3-héiy;M 4·! alommal SKUtetítuál, ™ 113 : azt jelenti, hogy a C2ÖHe1yzet -II -OH vagy -O csoporttal: szohszdíuáiL és ™ 114 azt jelenti, hegy· a C2ínhelyzei -H atommal sztibsztlioálk - azzal a teltétellel hogy a B, D és E képletekben, ha €3 és III között: kémiai köles vasa RÍ pátijáéig imlyag és .gyomor- és bélmndszed. zavarok; gyulladásos betegségek; szív- és érrendszeri betegségek: vesebántaimák; glaokórna, spasticltás; rák; ostgoporttsis; mambó!; kas zavarok; elhízás; szenvedély, itlggaséggel, visszaéléssel és visszaeséssel kapcsolatos betegségek;,pszl-chsátrku és neurológiai zavarok: neuroöegenerativ zavarok; autoimmun hepatitis és encephalitis; fajdaléin: és a két gyulladásos is ítbmtlkas betegségei közti! kikerüld patológiás állapot vagy rendellenesség kezelésében történd alkalmazásit 1 Λζ I. igénypont szerinti pregnenolonozárnwék. ahol a vegyüiet lényegében nem honver-fálódik aktív pregnenolon-s/ármnzékká egy alanynak történő adagolást kővetően. 3< .Az I. vagy 2. igénypont szerinti pregoenobroszármnzék, ahol a vegyidet (öl
    sepleuo vagy gyógy ászaákg; elfogadható Sega, ahol; ™ R I azt j elemi hogy a Cá-helyaetb-helyaetü -OH csoporttal vagy ::::0 csoporttal: szobszt imáit - R.2 azt jelenti, hogy a Clz-helyzet 1 -8 szénatomos alkdesoporttak halogénatommal vagy Bn- csoporttal szubsztimált, — R3 azt jelenti hogy a €20-helyzm -Oi l csoportiai sznbszömák, és — R4 az: jelenti hogy a 16-helyzei ~11 alommal szohsziimált, vagy ™™ R ] azt jelenti, hogy a €3Helyzet --Ö csoporttá! szubsztiiuáU, ' R2 jelejiit, iiögv a C- !74tolyz®t 14 óíktMómos vltgy ~ üta csoporttal szuhscih uálg -- R3 art jelenti, hogy a ClSÖptolyzet aíÖ Opepoíltál szubactiusák, os —~ R4 azt jelenő. h< -gj. a C ló-helyzet -II alommal azubsztituálí, példáit! a 1 Ta-nKáó-progea/.tccors vagy 1 Ta-bert/iI 4i M K vagy 2 . igénypont szerinti progROBolpp-azársmKék, alibi l a vegyiket (D g
    képletik vagy gyógyászati tag elfogadható sója., ahek R.l azt jelenig hogy a O-helyze! f>-állasú -NH*. Bn-O- vagy -Ni csoporttal szubsztituálL - R2 azt jekmh hogy a C17~hclyzct H atommal szubsztituak. kkt RS azt jalftli, hogy á Oihheiyzei o() esgpprkal szubazőüiálLée R4 act jelenti, hogy a Cló-hdyzet -H atommal szt-bs/tküák, például az S-pregnoia-bpsO^hooctl-lCI'-oig hp^mBinnptiignenoIoo vagy S^pteghio-áp-aaídO^SÍh ott, I, Az I. vagy 2. igénypont szerinti pregnenolon-sszánnazék. ahol a vegüket (D);
    képien!, νόμο ahol: ™ 1:1 azl Mead, hogy a C'Mtóyyai p~l!lpá 1-8 sMnatomos gikosleppoltaL balögép alJíftfáöi Iliiül·'vagy -Μΐ popölM szutedtaálb -12 azijéteMu hogy a Cif‘Aélyzéi Aíg -CIí vagy M álkvBllysagvltei 222 13 azt jeteaik hogy a CzCkhelyzet “€> csqpörtiál szabsz! ttuálh és 222 M ági jateatk hagy a Clié^káiyitt ~í! atommal sxutexdtaálh például p :l7a-#lli30uayivaidsá.gaaaDlM5: l:2a^héU2ll3p^0uorpségdedóléus dp^tluas^l^P mutll “pragnéHélun s 3 p-amta xi -1 Iá.» altil-prágéailölöus 1 'M-béuzi 1 A p-hletaxi -gt egnéuo Iöu, 3p'%tnul!övi-'l:?«"malil«ppguunuleu aagy lla'^euail-^p'éauaduylprggsieiiolaa.
  2. 6, Ív L vagy 2, igé«y|Ha«t·I^gfíitáí..pitgpinélopys^árptókí ahal a vygyület fi)):
    képiem, vagy gyégyásaaiiJag eltagadható sofa, ahol: 222 rí azt jelenti, hogy a €3-helyzet β-ál lásó -Öli csoporttal szubszütuálu -12 zztfofeail hogy g € 17-hély2áv h-dazádatadkis álltig 1A sgéháluntos éikualvagy Sa--esoponta I s ?. u ász t i t uá 11% 322 R3 azt jakiak hogy a €2Ő~heiyxet ~0 uappomal sgubsytltuali és 222 R4 azt jelenti, hogs a Cl 6-helyzet «Η atomtnaI szubazíiUsák, glldid! az ida-hfngilpregnepölöB, íla-pidpragaédöiuu, i%-metil-pregnenolon vág} 17- snetoxi-pregaenukaL % Az | . vagy 2. Igenypom szened pregnenolon-xzánnazék, ahaf a vegyüiet(D):
    ké|>kHü, vagy gyógyászai!lag elfogadható sója., ahol: ™ Rt azt jelenti, hogy a C3~he!yzet jkáltásd -Ol-l asogefdál szuhsziliaáfL - R2 azi jelenti hogy a € 17-helyzct »H atommal szubszblpli: — R3 azt jelenti hogy a C20-helyzei dh -ÖN vagy •MRSRR csopoTttal sgvfoygtttiÉh;? aho! RS és Ró egymástól függetlenül Ή vagy t~ff széBaiomos aikiigsógóít, el ™ 114 azt jelenig hogy a C t fohdyzci -Ή atommal szubsztituált, például a 20-de«sx ípregnenelon vagy 20-me!ü~ammo-S-p?egnen*3ft--ol. A .&amp;% í > vagy 2. igénypra szeriMl gtyitknóioB-sgáttóazek, alól a vegyitet (Eg
    kepleub vagy gybgyászaüiag elfogadható sója, ahf-i; azé Hl azrplenty hogy a 03-Aéfyaet -13 atobmiái izéhizdiaált,: R.3 azt jelenik hogy a CRö-helv/d -Π, -011 vagy :::0 csoporttal xzohszniuálí, év ™ ;<4 azt jelenti, hogy a C ló-helyzet -H atommal sznbszsituáU, példáid az 5,1 é«pregnadiet**2Ö~om
    4, Az I -i, igéóypöjaok bánavlyike azyHátkpvgPénólöE'kzáanazélí, hólyag és gyomor- ás bélrehdsaárl zavarok: szív- és érrendv/cd iMggságeib vevcbáutskoak; spaMkiiás: rák: ostoo- pomb; fl;dalom; és a'Mf tibroiilafi betegségei kózbl Mksröíö patológiás állapéi vagy rendellenesség kezelésében lórién# alkalmazásra. K), Ás I-S, 4gÍBvp(miöfe dármdglke sgerínn pregnenoton^zármazék eamiabis-szenvedéj) ♦ függőség, visszaélés, toxltek és visszaeséssel kapcsolatos betegségek kezelésében történő ajkaim· ázássá,
    1. Egy pregaenoion-szárinazék, ahol a vegyidéi } 7ü4>eBzik3pdluör~pjegnenoíon5 1 7o-ben.zib3p-benzlloxlpregnenolon, 3fbbemükmb 1 ?«-metii~pregnenolon, I7s~ benziipragyrenolom 3P»nietoxi-i?a-met il-pregnenoiun, 17a-a0i^3p~mflöxipfggaefíQÍ<m-'O.r' 17a“berad;-'3lbnunox1pregneaolen 12. igy gyógyászati készítmény, mely egy 1í. igénypont szemei vegyiddé! és: egy gyógy-, ászabjag elfogadható hordozót tartalma.
  3. 13. A I L igénypont szerMi vegyidéi emberi vagy 'állati test kezelési eljárásában történő alkalmazásra.
  4. 14. Λ I i. igénypont szerimi vegyesei hólyag és gyomor- és bélrendszeri zavarok; gyulladásos betegségek; szív- és érrendszeri betegségek; vesebántaimal ; gUuifcóma ; spasueiiás; rák- os-teppprosiá; membolikos zavarok; elhízás; szenvedéllyel,: függőséggé!, visszaéléssel, és visszaeséssel kapcsolatos betegségek; pszichiátriai és neurológiai zavarok; neurudegenCTativ zavarok; autoimmun hepatitis és encephalitis; fájdalom; reprodukciós zavarok cs a bőr gyulladásos és ílbmilkus betegségei k-Vül kikerülő patológiás állapot vagy rendellenesség kezelésében történő alkalmazásra.
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