HRP20231100T1 - Postupci za proizvodnju pirimidinilciklopentan spojeva - Google Patents
Postupci za proizvodnju pirimidinilciklopentan spojeva Download PDFInfo
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- HRP20231100T1 HRP20231100T1 HRP20231100TT HRP20231100T HRP20231100T1 HR P20231100 T1 HRP20231100 T1 HR P20231100T1 HR P20231100T T HRP20231100T T HR P20231100TT HR P20231100 T HRP20231100 T HR P20231100T HR P20231100 T1 HRP20231100 T1 HR P20231100T1
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- 238000000034 method Methods 0.000 title claims 23
- 238000002360 preparation method Methods 0.000 title claims 5
- KHXLVDUXFUNEQQ-UHFFFAOYSA-N 2-cyclopentylpyrimidine Chemical class C1CCCC1C1=NC=CC=N1 KHXLVDUXFUNEQQ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 34
- 125000000217 alkyl group Chemical group 0.000 claims 11
- -1 benzyloxycarbonyl (carbobenzyloxy, CBZ) Chemical class 0.000 claims 10
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 claims 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- 239000003446 ligand Substances 0.000 claims 6
- 108090000854 Oxidoreductases Proteins 0.000 claims 5
- 102000004316 Oxidoreductases Human genes 0.000 claims 5
- 239000003054 catalyst Substances 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 239000012327 Ruthenium complex Substances 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 3
- 230000008929 regeneration Effects 0.000 claims 3
- 238000011069 regeneration method Methods 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims 2
- CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 claims 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- 101710197978 NADPH-dependent oxidoreductase Proteins 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- NMLZYEWNUCRSRJ-UHFFFAOYSA-L [1-(2-diphenylphosphanylnaphthalen-1-yl)naphthalen-2-yl]-diphenylphosphane;ruthenium(2+);diacetate Chemical compound [Ru+2].CC([O-])=O.CC([O-])=O.C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 NMLZYEWNUCRSRJ-UHFFFAOYSA-L 0.000 claims 2
- 229910001413 alkali metal ion Inorganic materials 0.000 claims 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 2
- 125000000129 anionic group Chemical group 0.000 claims 2
- 150000001450 anions Chemical class 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims 2
- 150000004696 coordination complex Chemical class 0.000 claims 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims 2
- 150000004985 diamines Chemical class 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 claims 2
- 150000004678 hydrides Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 claims 2
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 claims 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims 2
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 150000003333 secondary alcohols Chemical class 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 239000000758 substrate Substances 0.000 claims 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 2
- RBVGOQHQBUPSGX-ZJZGAYNASA-N (2s,5s)-1-[2-[(2s,5s)-2,5-di(propan-2-yl)phospholan-1-yl]phenyl]-2,5-di(propan-2-yl)phospholane Chemical compound CC(C)[C@@H]1CC[C@@H](C(C)C)P1C1=CC=CC=C1P1[C@H](C(C)C)CC[C@H]1C(C)C RBVGOQHQBUPSGX-ZJZGAYNASA-N 0.000 claims 1
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 claims 1
- UNVGBIALRHLALK-UHFFFAOYSA-N 1,5-Hexanediol Chemical compound CC(O)CCCCO UNVGBIALRHLALK-UHFFFAOYSA-N 0.000 claims 1
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 claims 1
- 239000004912 1,5-cyclooctadiene Substances 0.000 claims 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims 1
- SXGZJKUKBWWHRA-UHFFFAOYSA-N 2-(N-morpholiniumyl)ethanesulfonate Chemical group [O-]S(=O)(=O)CC[NH+]1CCOCC1 SXGZJKUKBWWHRA-UHFFFAOYSA-N 0.000 claims 1
- QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 claims 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims 1
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 claims 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 1
- 108010050375 Glucose 1-Dehydrogenase Proteins 0.000 claims 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 1
- ACFIXJIJDZMPPO-NNYOXOHSSA-N NADPH Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](OP(O)(O)=O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 ACFIXJIJDZMPPO-NNYOXOHSSA-N 0.000 claims 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims 1
- ABGYJVGTLXSMBM-UHFFFAOYSA-N [2-[2-[bis(furan-2-yl)phosphanyl]-6-methoxyphenyl]-3-methoxyphenyl]-bis(furan-2-yl)phosphane Chemical compound COC=1C=CC=C(P(C=2OC=CC=2)C=2OC=CC=2)C=1C=1C(OC)=CC=CC=1P(C=1OC=CC=1)C1=CC=CO1 ABGYJVGTLXSMBM-UHFFFAOYSA-N 0.000 claims 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 239000012062 aqueous buffer Substances 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims 1
- 239000000872 buffer Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000006184 cosolvent Substances 0.000 claims 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 claims 1
- 239000004913 cyclooctene Substances 0.000 claims 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims 1
- DHCWLIOIJZJFJE-UHFFFAOYSA-L dichlororuthenium Chemical compound Cl[Ru]Cl DHCWLIOIJZJFJE-UHFFFAOYSA-L 0.000 claims 1
- PONXTPCRRASWKW-KBPBESRZSA-N diphenylethylenediamine Chemical compound C1([C@H](N)[C@@H](N)C=2C=CC=CC=2)=CC=CC=C1 PONXTPCRRASWKW-KBPBESRZSA-N 0.000 claims 1
- 239000008103 glucose Substances 0.000 claims 1
- 235000011187 glycerol Nutrition 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000003106 haloaryl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- YUWFEBAXEOLKSG-UHFFFAOYSA-N hexamethylbenzene Chemical compound CC1=C(C)C(C)=C(C)C(C)=C1C YUWFEBAXEOLKSG-UHFFFAOYSA-N 0.000 claims 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 229910021645 metal ion Inorganic materials 0.000 claims 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 claims 1
- 235000019796 monopotassium phosphate Nutrition 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 claims 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 229910001428 transition metal ion Inorganic materials 0.000 claims 1
- 125000001814 trioxo-lambda(7)-chloranyloxy group Chemical group *OCl(=O)(=O)=O 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/02—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from isocyanates with formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/16—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing two or more hetero rings
- C12P17/165—Heterorings having nitrogen atoms as the only ring heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Microbiology (AREA)
- Genetics & Genomics (AREA)
- General Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pyridine Compounds (AREA)
Claims (26)
1. Postupak za proizvodnju spojeva formule (II)
[image]
naznačen time, da obuhvaća asimetričnu hidrogenaciju spoja formule (IV)
[image]
uz uporabu katalizatora od metalnog kompleksa (C), pri čemu:
R1 je aminozaštitna skupina odabrana s popisa koji čine benzil, benziloksikarbonil (karbobenziloksi, CBZ), 9-fluorenilmetiloksikarbonil (Fmoc), p-metoksibenziloksikarbonil, p-nitrobenziloksikarbonil, terc-butoksikarbonil (BOC), i trifluoroacetil; i
M je metalni ion odabran s popisa koji čine ion alkalijskog metala, ion zemnoalkalijskog metala i ion prijelaznog metala;
pri čemu je katalizator od metalnog kompleksa (C) katalizator od rutenijevog kompleksa odabran od spoja formule (C1), (C2) ili (C3):
Ru(Z)2D (C1)
[Ru(Z)2-p(D)(L)m](Y)p (C2)
Ru(E)(E')(D)(F) (C3)
gdje:
D je kiralni fosfinski ligand;
L je neutralni ligand odabran od sljedećih: C2-7 alken, ciklookten, 1,3-heksadien, norbornadien, 1,5-ciklooktadien, benzen, heksametilbenzen, 1,3,5-trimetilbenzen, p-cimen, tetrahidrofuran, dimetilformamid, acetonitril, benzonitril, aceton, toluen, i metanol;
Z je anionski ligand odabran od sljedećih: hidrid, fluorid, klorid, bromid, η5-2,4-pentadienil, η5-2,4-dimetil-pentadienil, ili skupina A-COO-, uz uvjet da kada su dva Z vezana na Ru atom, tada oni mogu biti isti ili različiti;
A je C1-7 alkil, C1-7 haloalkil, aril, ili haloaril;
Y je nekoordinirajući anion koji se bira od sljedećih: fluorid, klorid, bromid, BF4-, ClO4-, SbF6-, PF6-, B(fenil)4-, B(3,5-di-trifluorometil-fenil)4-, CF3SO3-, i C6H5SO3-;
F je opcionalno kiralni diamin;
E i E' su oba ioni halogena, ili je E hidrid i E' je BH4-;
m je 1, 2, 3 ili 4; i
p je 1 ili 2.
2. Postupak prema patentnom zahtjevu 1, naznačen time, da R1 je terc-butoksikarbonil (BOC).
3. Postupak prema bilo kojem od patentnih zahtjeva 1 do 2, naznačen time, da M je ion alkalijskog metala; ili time, da M je Na+.
4. Postupak prema patentnom zahtjevu 1, naznačen time, da je anionski ligand (Z) neovisno odabran od klorida, bromida, OAc, i TFA.
5. Postupak prema patentnom zahtjevu 1, naznačen time, da nekoordinarajući anion (Y) jest BF4-.
6. Postupak prema patentnom zahtjevu 1, naznačen time, da kiralni diamin F je (1S,2S)-1,2-difeniletilendiamin (S,S-DPEN).
7. Postupak prema patentnom zahtjevu 1, naznačen time, da se kiralni fosfinski ligand D bira od spoja formule (D1) do (D12):
[image]
[image]
[image]
gdje:
R11 je C1-7 alkil, C1-7 alkoksi, hidroksi, ili C1-7 alkil-C(O)O-;
svaki od R12 i R13 je neovisno vodik, C1-7 alkil, C1-7 alkoksi, ili di(C1-7 alkil)amino; ili
R11 i R12 koji su vezani na istu fenilnu skupinu, ili R12 i R13 koji su vezani na istu fenilnu skupinu, kada se uzimaju zajedno su -X-(CH2)r-Y-, pri čemu X je -O-, ili -C(O)O-, Y je -O-, -N(niži alkil)-, ili -CF2-, i
r je cijeli broj od 1 do 6; ili
dva R11 kada se uzimaju zajedno su -O-(CH2)s-O-, ili -O-CH(CH3)-(CH2)s-CH(CH3)-O-, gdje s je cijeli broj od 1 do 6; ili
R11 i R12, ili R12 i R13, zajedno s ugljikovim atomima s kojima su vezani, tvore naftil, tetrahidronaftil ili dibenzofuran prsten;
svaki od R14 i R15 je neovisno C1-7 alkil, C3-8 cikloalkil, fenil, naftil, ili heteroaril, opcionalno supstituirani s 1 do 7 supstituenata neovisno odabranih iz skupine koju čine C1-7 alkil, C1-7 alkoksi, di(C1-7 alkil)amino, morfolinil, fenil, tri(C1-7 alkil)silil, C1-7 alkoksikarbonil, hidroksikarbonil, hidroksisulfonil, (CH2)t-OH, i (CH2)t-NH2, gdje t je cijeli broj od 1 do 6;
R16 je C1-7 alkil;
R17 je C1-7 alkil; i
R18 je neovisno aril, heteroaril, C3-8 cikloalkil, ili C1-7 alkil.
8. Postupak prema patentnom zahtjevu 1 ili 7, naznačen time, da kiralni fosfinski ligand (D) jest (S)-BINAP.
9. Postupak prema patentnom zahtjevu 1, naznačen time, da se katalizator od rutenijevog kompleksa bira iz skupine koju čine:
Ru(TFA)2((R)-3,5-Xil-BINAP),
Ru(OAc)2((S)-2-Furil-MeOBIPHEP),
Ru(OAc)2((S)-BINAP),
[Ru(OAc)2((S)-BINAP)]AlCl3,
Ru(TFA)2((S)-BINAP),
Ru(TFA)2((S)-BINAPHANE),
Ru(TFA)2((S)-BIPHEMP),
Ru(OAc)2((S)-MeOBIPHEP),
Ru(TFA)2((S)-TMBTP),
Ru(TFA)2((S,S)-iPr-DUPHOS),
[Ru((R)-BINAP)(pCym)(AN)](BF4)2,
[RuBr((S)-BINAP)(C6H6)]Br,
[RuCl((S)-BINAP)(C6H6)]BF4,
[RuI((S)-BINAP)(C6H6)]I,
[Ru((S)-BINAP)(AN))4](BF4)2, i
RuCl2((S)-pTol-BINAP)(S,S-DPEN); ili
pri čemu katalizator od rutenijevog kompleksa jest Ru(TFA)2((S)-BINAP).
10. Postupak za proizvodnju spojeva formule (III)
[image]
naznačen time, da obuhvaća asimetričnu redukciju spoja formule (V)
[image]
kataliziranu putem oksidoreduktaze, pri čemu:
R2 je aminozaštitna skupina odabrana iz popisa koji čine benzil, benziloksikarbonil (karbobenziloksi, CBZ), 9-fluorenilmetiloksikarbonil (Fmoc), p-metoksibenziloksikarbonil, p-nitrobenziloksikarbonil, terc-butoksikarbonil (BOC), i trifluoroacetil.
11. Postupak prema patentnom zahtjevu 10, naznačen time, da R2 jest terc-butoksikarbonil (BOC).
12. Postupak prema patentnom zahtjevu 10, naznačen time, da oksidoreduktaza katalizira asimetričnu redukciju spoja formule (V) u spoj formule (III) s dijastereoselektivnošću od najmanje 95% dijastereomernog viška (de).
13. Postupak prema patentnom zahtjevu 10, naznačen time, da se asimetrična redukcija spoja formule (V) u spoj formule (III) katalizira putem oksidoreduktaze u prisutnosti kofaktora.
14. Postupak prema patentnom zahtjevu 13, naznačen time, da je kofaktor koji se oksidira u asimetričnoj redukciji spoja formule (V) u spoj formule (III), NADH ili NADPH.
15. Postupak prema patentnom zahtjevu 13, naznačen time, da se kofaktor in situ regenerira putem: (a) regeneracije enzimski spojenog kofaktora uz uporabu glukoze i glukozne dehidrogenaze kao kosupstrata; ili (b) regeneracije kofaktora spojenog sa supstratom uz uporabu sekundarnog alkohola kao kosupstrata.
16. Postupak prema patentnom zahtjevu 15, naznačen time, da se za regeneraciju kofaktora spojenog sa supstratom bira sekundarni alkohol kao kosupstrat od sljedećih: 2-propanol, 2-butanol, butan-1,4-diol, 2-pentanol, pentan-1,5-diol, 4-metil-2-pentanol, 2-heksanol, heksan-1,5-diol, 2-heptanol, ili 2-oktanol.
17. Postupak prema patentnom zahtjevu 10, naznačen time, da oksidoreduktaza je dijastereoselektivna NADPH-ovisna oksidoreduktaza koja se bira iz popisa koji čine KRED-NADPH-111, KRED-NADPH-112, KRED-NADPH-113, KRED-NADPH-114, KRED-NADPH-115, KRED-NADPH-121, KRED-NADPH-123, KRED-NADPH-145, KRED-NADPH-155, A231, KRED-NADPH-136, KRED-X1, KRED-X2, KRED-X1-P1B06, KRED-X1.1-P1F01, KRED-X1.1-P1H10, KRED-X1.1-P1G11, KRED-X1.1-P1C04, KRED-X1.1-P1C11, i KRED-X1.1-P1C08; ili
time, da oksidoreduktaza je dijastereoselektivna NADPH-ovisna oksidoreduktaza odabrana iz popisa koji čine KRED-X1, KRED-X2, KRED-X1-P1B06, KRED-X1.1-P1F01, KRED-X1.1-P1H10, KRED-X1.1-P1G11, KRED-X1.1-P1C04, KRED-X1.1-P1C11, i KRED-X1.1-P1C08.
18. Postupak prema patentnom zahtjevu 10, naznačen time, da se asimetrična redukcija spoja formule (V) u spoj formule (III), provodi u vodenom mediju u prisutnosti jednog ili više organskih kootapala.
19. Postupak prema patentnom zahtjevu 18, naznačen time, da se organska kootapala nalaze u ukupnoj koncentraciji od 1 do 50% volumena.
20. Postupak prema patentnom zahtjevu 19, naznačen time, da se organska kootapala biraju iz popisa koji čine glicerin, 2-propanol, dietileter, terc-butilmetileter, diizopropileter, dibutileter, metiltetrahidrofuran, etilacetat, butilacetat, toluen, heptan, heksan, cikloheksen i njihove mješavine.
21. Postupak prema patentnom zahtjevu 10, naznačen time, da se asimetrična redukcija spoja formule (V) u spoj formule (III) provodi u vodenom puferu.
22. Postupak prema patentnom zahtjevu 21, naznačen time, da pufer je 2-(N-morfolino)etansulfonska kiselina (MES) ili kalijev divodik fosfat (PBS).
23. Pripravak, naznačen time, da sadrži spoj formule (VI)
[image]
i između 1 ppb i 100 ppm spoja formule (I)
[image]
pri čemu je R1 kao što je definiran u bilo kojem od patentnih zahtjeva 1 ili 2; ili
pripravak sadrži spoj formule (VI) i između 1 ppb i 1 ppm spoja formule (I), gdje je R1 kao što je definiran u bilo kojem od patentnih zahtjeva 1 ili 2.
24. Pripravak, naznačen time, da sadrži spoj formule (I)
[image]
i između 1 ppb i 100 ppm spoja formule (II)
[image]
pri čemu su R1 i M kao što su definirani u bilo kojem od patentnih zahtjeva 1 do 3; ili
pripravak sadrži spoj formule (I) i između 1 ppb i 1 ppm spoja formule (II), gdje su R1 i M kao što su definirani u bilo kojem od patentnih zahtjeva 1 do 3.
25. Pripravak, naznačen time, da sadrži spoj formule (I)
[image]
i između 1 ppb i 100 ppm spoja formule (III)
[image]
pri čemu je R1 kao što je definiran u bilo kojem od patentnih zahtjeva 1 ili 2, i R2 je kao što je definiran u bilo kojem od patentnih zahtjeva 10 ili 11; ili
pripravak sadrži spoj formule (I) i između 1 ppb i 1 ppm spoja formule (III), gdje je R1 kao što je definiran u bilo kojem od patentnih zahtjeva 1 ili 2, i R2 je kao što je definiran u bilo kojem od patentnih zahtjeva 10 ili 11.
26. Pripravak, naznačen time, da sadrži spoj formule (I)
[image]
i između 1 ppb i 100 ppm spoja formule (II)
[image]
i između 1 ppb i 100 ppm spoja formule (III)
[image]
pri čemu su R1, R2 i M kao što su definirani u bilo kojem od patentnih zahtjeva 1 do 3, 10 ili 11; ili
pripravak sadrži spoj formule (I) i između 1 ppb i 1 ppm spoja formule (II), i između 1 ppb i 1 ppm spoja formule (III), gdje su R1, R2 i M kao što su definirani u bilo kojem od patentnih zahtjeva 1 do 3, 10 ili 11.
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