HRP20110963T1 - Egzo- i diastereo-selektivne sinteze analoga himbacina - Google Patents
Egzo- i diastereo-selektivne sinteze analoga himbacina Download PDFInfo
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- HRP20110963T1 HRP20110963T1 HR20110963T HRP20110963T HRP20110963T1 HR P20110963 T1 HRP20110963 T1 HR P20110963T1 HR 20110963 T HR20110963 T HR 20110963T HR P20110963 T HRP20110963 T HR P20110963T HR P20110963 T1 HRP20110963 T1 HR P20110963T1
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- FMPNFDSPHNUFOS-LPJDIUFZSA-N himbacine Chemical class C(/[C@@H]1[C@H]2CCCC[C@@H]2C[C@@H]2C(=O)O[C@H]([C@H]12)C)=C\[C@H]1CCC[C@H](C)N1C FMPNFDSPHNUFOS-LPJDIUFZSA-N 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 22
- 238000000034 method Methods 0.000 claims 16
- 229940125773 compound 10 Drugs 0.000 claims 12
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims 12
- 238000006243 chemical reaction Methods 0.000 claims 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 9
- 239000002904 solvent Substances 0.000 claims 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims 5
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims 4
- -1 C6 alkyl carbonyl compound Chemical class 0.000 claims 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 2
- 229910004879 Na2S2O5 Inorganic materials 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000003377 acid catalyst Substances 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 230000002051 biphasic effect Effects 0.000 claims 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
- 150000007529 inorganic bases Chemical class 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 2
- 235000015320 potassium carbonate Nutrition 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 150000003335 secondary amines Chemical class 0.000 claims 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 2
- 235000017550 sodium carbonate Nutrition 0.000 claims 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 claims 2
- 235000010262 sodium metabisulphite Nutrition 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 239000003849 aromatic solvent Substances 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 229910000024 caesium carbonate Inorganic materials 0.000 claims 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims 1
- 239000000920 calcium hydroxide Substances 0.000 claims 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims 1
- 235000011116 calcium hydroxide Nutrition 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 125000005265 dialkylamine group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 229910052808 lithium carbonate Inorganic materials 0.000 claims 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims 1
- 229910000032 lithium hydrogen carbonate Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 235000010755 mineral Nutrition 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 239000011736 potassium bicarbonate Substances 0.000 claims 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims 1
- 235000015497 potassium bicarbonate Nutrition 0.000 claims 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 claims 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims 1
- 235000010263 potassium metabisulphite Nutrition 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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- 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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- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/10—Preparation of nitro compounds by substitution of functional groups by nitro groups
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- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
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- C07C205/55—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
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- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and unsaturated
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- C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
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- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
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- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
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- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/56—Radicals substituted by oxygen atoms
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
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- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Abstract
Spoj izabran iz grupe koju čine: Patent sadrži još 14 patentnih zahtjeva.
Claims (15)
1. Spoj izabran iz grupe koju čine:
[image]
2. Postupak za pripremu spoja 10:
[image]
pri čemu taj postupak sadrži:
(a) reakciju akroleina sa CH3NO2 u prisustvu neorganske baze u C1-C8 alkoholu da se proizvede čisti spoj 8:
[image]
(b) reakciju sirovog spoja 8 sa metal bisulfitom da se proizvede spoj 9:
[image]
(c) tretman spoja 9 sa C1 do C6 alkil karbonil spojem i karbonatnom bazom u bifaznom sustavu otapala da se proizvede prečišćeni spoj 8; i
(d) reakciju navedenog prečišćenog spoja 8 sa sekundarnim aminom i karboksilnom kiselinom u prvom otapalu da se proizvede spoj 10.
3. Postupak prema patentnom zahtjevu 2, u kojem:
navedena neorganska baza je izabrana iz grupe koju čine LiOH, KOH, NaOH, Ca(OH)2, Li2CO3, Na2CO3, K2CO3 i Cs2CO3; i/ili
navedeni alkohol je izabran iz grupe koju čine metanol, etanol, propanol, izopropanol, butanol, sek-butanol, t-butanol, pentanol, oktanol i smjese od 2 ili više navedenih spojeva.
4. Postupak prema patentnom zahtjevu 2 ili 3, u kojem je navedeni metal bisulfit izabran iz grupe koju čine NaHSO3, KHSO3, Na2S2O5 i K2S2O5.
5. Postupak prema bilo kojem od patentnih zahtjeva 2 do 4, u kojem:
navedeni C1 do C6 alkil karbonil spoj je izabran iz grupe koju čine acetaldehid, aceton, glioksilna kiselina i glioksilat; i/ili
navedena karbonatna baza je izabrana iz grupe koju čine LiHCO3, NaHCO3, KHCO3, L12CO3, Na2CO3 i K2CO3.
6. Postupak prema bilo kojem od patentnih zahtjeva 2 do 5, u kojem navedeni bifazni sustav otapala sadrži vodu i otapalo koji je mješljiv sa vodom.
7. Postupak prema bilo kojem od patentnih zahtjeva 2 do 6, u kojem:
navedeni sekundarni amin je izabran iz grupe koju čine piperidin, pirolidin, piperazin, dialkilamini i diarilalkilamini,
posebno pirolidin; i/ili
navedena karboksilna kiselina je izabrana iz grupe koju čine alifatične i aromatične karboksilne kiseline, posebno benzoeva kiselina.
8. Postupak prema bilo kojem od patentnih zahtjeva 2 do 7, u kojem je navedeno prvo otapalo izabrano iz grupe koju čine CH2Cl2, hlorobenzen, t-butilmetiletar i toluen.
9. Postupak za pripremu spoja 10:
[image]
koji sadrži:
(a) reakciju akroleina sa CH3NO2 da bi se proizveo spoj 8:
[image]
(b) reakciju spoja 8 sa Na2S2O5 da se proizvede spoj 9:
[image]
i
(c) reakciju spoja 9 sa kiselinom da se proizvede spoj 10.
10. Postupak prema patentnom zahtjevu 9, u kojem je navedena kiselina glioksilna kiselina.
11. Postupak za pripremu spoja 6:
[image]
koji sadrži pripremu spoja 10 pomoću postupka prema bilo kojem od patentnih zahtjeva 2 do 10 i konverziju spoja 10 u spoj 6.
12. Postupak prema patentnom zahtjevu 11, u kojem korak prevođenja spoja 10 u spoj 6 sadrži reakciju spoja 10 sa Wittig reagensom ili sa malonskom kiselinom.
13. Postupak prema patentnom zahtjevu 11, u kojem navedeni korak konverzije spoja 10 u spoj 6 sadrži korake:
(a) reakcije spoja 10 sa Ph3P=CHCOOR8 da se proizvede spoj 6A:
[image]
i
(b) hidrolize spoja 6A u spoj 6 tretmanom spoja 6A baznim katalizatorom ili kiselim katalizatorom:
[image]
u kojem:
R8 je C1 do C10 alkil ili arilalkil;
navedeni bazni katalizator je poželjno izabran iz grupe koju čine alkalne hidroksidne, karbonatne i fosfatne baze; i
navedeni kiseli katalizator je poželjno izabran iz grupe koju čine mineralne i organske kiseline.
14. Postupak prema patentnom zahtjevu 11, u kojem navedeni korak konverzije spoja 10 u spoj 6 sadrži reakciju spoja 10 sa malonskom kiselinom u drugom otapalu, pri čemu je navedeno drugo otapalo poželjno izabrano iz grupe koju čine halogenizirana otapala, aromatična otapala i otapala koja sadrže dušik, posebno iz grupe koju čine piridin i toluen.
15. Postupak prema patentnom zahtjevu 14, koji dalje sadrži upotrebu katalizatora na bazi dušika za ubrzavanje reakcije, pri čemu je navedeni katalizator na bazi dušika izabran iz grupe koju čine piperidin, pirolidin, piperazin, piridin i trietilamin.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US64446405P | 2005-01-14 | 2005-01-14 |
Publications (1)
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HRP20110963T1 true HRP20110963T1 (hr) | 2012-01-31 |
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HR20100218T HRP20100218T1 (hr) | 2005-01-14 | 2010-04-16 | Egzo- i dijastereoselektivna sinteza analoga himbacina |
HR20110963T HRP20110963T1 (hr) | 2005-01-14 | 2011-12-21 | Egzo- i diastereo-selektivne sinteze analoga himbacina |
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HR20100218T HRP20100218T1 (hr) | 2005-01-14 | 2010-04-16 | Egzo- i dijastereoselektivna sinteza analoga himbacina |
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US (4) | US7605275B2 (hr) |
EP (4) | EP2196468B1 (hr) |
JP (3) | JP4681616B2 (hr) |
CN (2) | CN101193880B (hr) |
AR (1) | AR056919A1 (hr) |
AT (2) | ATE530516T1 (hr) |
CA (2) | CA2875768C (hr) |
CY (2) | CY1109896T1 (hr) |
DE (1) | DE602006012450D1 (hr) |
DK (2) | DK2206697T3 (hr) |
ES (3) | ES2412981T3 (hr) |
HK (1) | HK1108893A1 (hr) |
HR (2) | HRP20100218T1 (hr) |
ME (1) | ME01967B (hr) |
MX (1) | MX2007008665A (hr) |
PL (2) | PL1848705T3 (hr) |
PT (2) | PT1848705E (hr) |
RS (2) | RS52117B (hr) |
SG (2) | SG192505A1 (hr) |
SI (2) | SI1848705T1 (hr) |
WO (1) | WO2006076415A2 (hr) |
ZA (1) | ZA200706711B (hr) |
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US7488742B2 (en) * | 2000-06-15 | 2009-02-10 | Schering Corporation | Thrombin receptor antagonists |
DK2206697T3 (da) | 2005-01-14 | 2012-02-13 | Schering Corp | Exo- og diastereo-selektive synteser af himbacinanaloger |
AR052871A1 (es) * | 2005-01-14 | 2007-04-11 | Schering Corp | Una sintesis exo-selectiva de analogos de himbacina |
WO2006076564A1 (en) * | 2005-01-14 | 2006-07-20 | Schering Corporation | Synthesis of himbacine analogs |
WO2007075964A2 (en) * | 2005-12-22 | 2007-07-05 | Schering Corporation | Thrombin receptor antagonists as prophylaxis to complications from cardiopulmonary surgery |
US7553987B2 (en) * | 2006-06-30 | 2009-06-30 | Schering Corporation | Synthesis of 3-(5-nitrocyclohex-1-enyl) acrylic acid and esters thereof |
AR061727A1 (es) * | 2006-06-30 | 2008-09-17 | Schering Corp | Sintesis de dietil [[ 5- ( 3-fluorofenil) -piridin -2il] metil] fosfonato |
WO2008076316A2 (en) * | 2006-12-15 | 2008-06-26 | Schering Corporation | Bisulfite purification of an alpha-keto amide |
CN101918019B (zh) | 2007-10-08 | 2014-11-26 | 奥里尼亚制药有限公司 | 包含钙调神经磷酸酶抑制剂或mTOR抑制剂的眼科组合物 |
JP5432910B2 (ja) * | 2007-10-24 | 2014-03-05 | メルク・シャープ・アンド・ドーム・コーポレーション | ドデカヒドロ−ナフト−フラニル−カルバミン酸エステル中間体調製のための高純度合成プロセス |
JP5945593B2 (ja) * | 2011-06-21 | 2016-07-05 | ブルースター・シリコーンズ・フランス・エスアエス | ヒドロシリル化反応抑制剤及び安定な硬化性シリコーン組成物を調製するためのその使用 |
CN105330689B (zh) * | 2014-08-08 | 2018-08-17 | 博瑞生物医药(苏州)股份有限公司 | 制备Himbacine类似物中间体的制备方法 |
CN105985303B (zh) * | 2015-02-13 | 2020-08-14 | 上海彩迩文生化科技有限公司 | 抗凝血剂的制备方法、中间体及其制备方法 |
CN105348241B (zh) * | 2015-12-11 | 2017-09-05 | 南京华威医药科技开发有限公司 | 一种硫酸沃拉帕沙中间体的合成方法 |
US11247940B2 (en) | 2016-10-26 | 2022-02-15 | The Regents Of The University Of California | Efficient integration of manufacturing of upcycled concrete product into power plants |
CN106749138B (zh) * | 2016-12-07 | 2019-08-16 | 扬子江药业集团四川海蓉药业有限公司 | 一种硫酸沃拉帕沙中间体醛的制备方法 |
CN106866450B (zh) * | 2017-01-13 | 2019-01-11 | 阜阳欣奕华材料科技有限公司 | 硫酸沃拉帕沙中间体的制备方法 |
CN108658910B (zh) * | 2017-03-29 | 2020-11-03 | 北京新领先医药科技发展有限公司 | 一种沃拉帕沙中间体1-α的制备方法 |
US20190224275A1 (en) | 2017-05-12 | 2019-07-25 | Aurinia Pharmaceuticals Inc. | Protocol for treatment of lupus nephritis |
WO2019006352A1 (en) * | 2017-06-30 | 2019-01-03 | The Regents Of The University Of California | CO2 MINERALIZATION IN PRODUTED AND INDUSTRIAL EFFLUENT WATER BY PH CHANGE CARBONATION |
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DE60317493T3 (de) * | 2002-04-16 | 2018-07-12 | Merck Sharp & Dohme Corp. | Trizyklische thrombin rezeptor antagonisten |
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AR052871A1 (es) * | 2005-01-14 | 2007-04-11 | Schering Corp | Una sintesis exo-selectiva de analogos de himbacina |
WO2006076564A1 (en) * | 2005-01-14 | 2006-07-20 | Schering Corporation | Synthesis of himbacine analogs |
US7541471B2 (en) * | 2005-01-14 | 2009-06-02 | Schering Corporation | Synthesis of himbacine analogs |
DK2206697T3 (da) | 2005-01-14 | 2012-02-13 | Schering Corp | Exo- og diastereo-selektive synteser af himbacinanaloger |
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