NO316070B1 - Cykliske forbindelser og fremgangsmåter for deres fremstilling - Google Patents
Cykliske forbindelser og fremgangsmåter for deres fremstilling Download PDFInfo
- Publication number
- NO316070B1 NO316070B1 NO19975391A NO975391A NO316070B1 NO 316070 B1 NO316070 B1 NO 316070B1 NO 19975391 A NO19975391 A NO 19975391A NO 975391 A NO975391 A NO 975391A NO 316070 B1 NO316070 B1 NO 316070B1
- Authority
- NO
- Norway
- Prior art keywords
- compound
- formula
- group
- carbon atoms
- stated
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims description 19
- 150000001923 cyclic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 125
- 125000004432 carbon atom Chemical group C* 0.000 claims description 68
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 125000001424 substituent group Chemical group 0.000 claims description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
- 125000001624 naphthyl group Chemical group 0.000 claims description 18
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 16
- -1 amino compound Chemical class 0.000 claims description 14
- 230000015572 biosynthetic process Effects 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 239000003586 protic polar solvent Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000006317 isomerization reaction Methods 0.000 claims description 3
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 claims 1
- 229940125758 compound 15 Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 239000003242 anti bacterial agent Substances 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 50
- 239000002904 solvent Substances 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 230000003287 optical effect Effects 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 238000005755 formation reaction Methods 0.000 description 9
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 7
- 239000012230 colorless oil Substances 0.000 description 7
- 239000005457 ice water Substances 0.000 description 7
- 239000012266 salt solution Substances 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 6
- JSBSBOIAHOITDX-UHFFFAOYSA-N ethyl 1-formylcyclopropane-1-carboxylate Chemical compound CCOC(=O)C1(C=O)CC1 JSBSBOIAHOITDX-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- RKOTXQYWCBGZLP-UHFFFAOYSA-N N-[(2,4-difluorophenyl)methyl]-2-ethyl-9-hydroxy-3-methoxy-1,8-dioxospiro[3H-pyrido[1,2-a]pyrazine-4,3'-oxolane]-7-carboxamide Chemical compound CCN1C(OC)C2(CCOC2)N2C=C(C(=O)NCC3=C(F)C=C(F)C=C3)C(=O)C(O)=C2C1=O RKOTXQYWCBGZLP-UHFFFAOYSA-N 0.000 description 5
- 239000007868 Raney catalyst Substances 0.000 description 5
- 229910000564 Raney nickel Inorganic materials 0.000 description 5
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- 235000002597 Solanum melongena Nutrition 0.000 description 3
- 244000061458 Solanum melongena Species 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- HFECGNQJEGCPEP-JSGCOSHPSA-N ethyl 1-[(r)-cyano-[[(1s)-1-phenylethyl]amino]methyl]cyclopropane-1-carboxylate Chemical compound CCOC(=O)C1([C@@H](N[C@@H](C)C=2C=CC=CC=2)C#N)CC1 HFECGNQJEGCPEP-JSGCOSHPSA-N 0.000 description 3
- HFECGNQJEGCPEP-GXTWGEPZSA-N ethyl 1-[(s)-cyano-[[(1s)-1-phenylethyl]amino]methyl]cyclopropane-1-carboxylate Chemical compound CCOC(=O)C1([C@H](N[C@@H](C)C=2C=CC=CC=2)C#N)CC1 HFECGNQJEGCPEP-GXTWGEPZSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229960001367 tartaric acid Drugs 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 description 2
- RTCUCQWIICFPOD-VIFPVBQESA-N (1s)-1-naphthalen-1-ylethanamine Chemical compound C1=CC=C2C([C@@H](N)C)=CC=CC2=C1 RTCUCQWIICFPOD-VIFPVBQESA-N 0.000 description 2
- RSAMYOOSQGZDDT-UHFFFAOYSA-N 1,2-dichloroethane;ethanol;hexane Chemical compound CCO.ClCCCl.CCCCCC RSAMYOOSQGZDDT-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000006345 epimerization reaction Methods 0.000 description 2
- IZPYNZLFBUQGCZ-UHFFFAOYSA-N ethyl 1-methylcyclopropane-1-carboxylate Chemical compound CCOC(=O)C1(C)CC1 IZPYNZLFBUQGCZ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 150000007660 quinolones Chemical class 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- OUVZHZAOWDHBOU-YFKPBYRVSA-N (1s)-1-(2,4-dichlorophenyl)ethanamine Chemical compound C[C@H](N)C1=CC=C(Cl)C=C1Cl OUVZHZAOWDHBOU-YFKPBYRVSA-N 0.000 description 1
- NBJDRZKPGXNVQI-YFKPBYRVSA-N (1s)-1-(2,4-dinitrophenyl)ethanamine Chemical compound C[C@H](N)C1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O NBJDRZKPGXNVQI-YFKPBYRVSA-N 0.000 description 1
- DYNJVRIGZRAWQN-YFKPBYRVSA-N (1s)-1-(3,5-dichlorophenyl)ethanamine Chemical compound C[C@H](N)C1=CC(Cl)=CC(Cl)=C1 DYNJVRIGZRAWQN-YFKPBYRVSA-N 0.000 description 1
- USMLPLKAUZIPIG-YFKPBYRVSA-N (1s)-1-(3,5-dinitrophenyl)ethanamine Chemical compound C[C@H](N)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 USMLPLKAUZIPIG-YFKPBYRVSA-N 0.000 description 1
- PINPOEWMCLFRRB-LURJTMIESA-N (1s)-1-(4-chlorophenyl)ethanamine Chemical compound C[C@H](N)C1=CC=C(Cl)C=C1 PINPOEWMCLFRRB-LURJTMIESA-N 0.000 description 1
- JTDGKQNNPKXKII-ZETCQYMHSA-N (1s)-1-(4-methoxyphenyl)ethanamine Chemical compound COC1=CC=C([C@H](C)N)C=C1 JTDGKQNNPKXKII-ZETCQYMHSA-N 0.000 description 1
- AQFLVLHRZFLDDV-VIFPVBQESA-N (1s)-1-phenylpropan-1-amine Chemical compound CC[C@H](N)C1=CC=CC=C1 AQFLVLHRZFLDDV-VIFPVBQESA-N 0.000 description 1
- ZICDZTXDTPZBKH-HNNXBMFYSA-N (1s)-2-(4-methylphenyl)-1-phenylethanamine Chemical compound C1=CC(C)=CC=C1C[C@H](N)C1=CC=CC=C1 ZICDZTXDTPZBKH-HNNXBMFYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZRXHLJNBNWVNIM-UHFFFAOYSA-N 3-methyl-1-benzofuran Chemical compound C1=CC=C2C(C)=COC2=C1 ZRXHLJNBNWVNIM-UHFFFAOYSA-N 0.000 description 1
- RAEVOBPXEHVUFY-LURJTMIESA-N 4187-53-5 Chemical compound C[C@H](N)C1=CC=C([N+]([O-])=O)C=C1 RAEVOBPXEHVUFY-LURJTMIESA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- VRAIHTAYLFXSJJ-UHFFFAOYSA-N alumane Chemical class [AlH3].[AlH3] VRAIHTAYLFXSJJ-UHFFFAOYSA-N 0.000 description 1
- VMWZRHGIAVCFNS-UHFFFAOYSA-J aluminum;lithium;tetrahydroxide Chemical compound [Li+].[OH-].[OH-].[OH-].[OH-].[Al+3] VMWZRHGIAVCFNS-UHFFFAOYSA-J 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229960001270 d- tartaric acid Drugs 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- ZOGHDTBRWUEJDP-UHFFFAOYSA-N diethylalumanylium;cyanide Chemical compound N#[C-].CC[Al+]CC ZOGHDTBRWUEJDP-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- GTJJIQMUKDPGCA-UHFFFAOYSA-N ethyl 1-[(benzylamino)-cyanomethyl]cyclopropane-1-carboxylate Chemical compound C=1C=CC=CC=1CNC(C#N)C1(C(=O)OCC)CC1 GTJJIQMUKDPGCA-UHFFFAOYSA-N 0.000 description 1
- HFECGNQJEGCPEP-OCCSQVGLSA-N ethyl 1-[(r)-cyano-[[(1r)-1-phenylethyl]amino]methyl]cyclopropane-1-carboxylate Chemical compound CCOC(=O)C1([C@@H](N[C@H](C)C=2C=CC=CC=2)C#N)CC1 HFECGNQJEGCPEP-OCCSQVGLSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/31—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/54—Spiro-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Mechanical Coupling Of Light Guides (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12775695 | 1995-05-26 | ||
| JP30791395 | 1995-11-27 | ||
| PCT/JP1996/001373 WO1996037470A1 (fr) | 1995-05-26 | 1996-05-23 | Procedes de preparation de composes cycliques |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO975391D0 NO975391D0 (no) | 1997-11-24 |
| NO975391L NO975391L (no) | 1998-01-26 |
| NO316070B1 true NO316070B1 (no) | 2003-12-08 |
Family
ID=26463637
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19975391A NO316070B1 (no) | 1995-05-26 | 1997-11-24 | Cykliske forbindelser og fremgangsmåter for deres fremstilling |
| NO20031884A NO324846B1 (no) | 1995-05-26 | 2003-04-25 | Cykliske forbindelser og fremgangsmater for deres fremstilling |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20031884A NO324846B1 (no) | 1995-05-26 | 2003-04-25 | Cykliske forbindelser og fremgangsmater for deres fremstilling |
Country Status (15)
| Country | Link |
|---|---|
| US (3) | US5856518A (zh) |
| EP (2) | EP0829473B1 (zh) |
| KR (1) | KR100399512B1 (zh) |
| CN (2) | CN1190421C (zh) |
| AT (1) | ATE221876T1 (zh) |
| AU (1) | AU5778996A (zh) |
| CA (1) | CA2221946C (zh) |
| DE (1) | DE69622862T2 (zh) |
| DK (1) | DK0829473T3 (zh) |
| EA (1) | EA000867B1 (zh) |
| ES (1) | ES2181886T3 (zh) |
| NO (2) | NO316070B1 (zh) |
| PT (1) | PT829473E (zh) |
| TW (1) | TW453986B (zh) |
| WO (1) | WO1996037470A1 (zh) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5948935A (en) * | 1997-01-23 | 1999-09-07 | Boehringer Ingelheim (Canada) Ltd. | Process and intermediates for (s)-α-amino-1-carboxycyclopentaneacetic acid |
| US6197974B1 (en) * | 1998-10-26 | 2001-03-06 | Abbott Laboratories | Enantioselective synthesis of 3-aminopyrrolidines |
| US6191306B1 (en) * | 1999-08-03 | 2001-02-20 | Eastman Chemical Company | Process for the preparation of cyclopropylglycine |
| CN101544581B (zh) * | 2000-08-08 | 2013-02-06 | 第一三共株式会社 | 双环化合物的制备方法及其中间体 |
| CN1184221C (zh) * | 2001-08-08 | 2005-01-12 | 中国医学科学院医药生物技术研究所 | 有7－(7－氨甲基－5－氮杂螺[2,4]庚烷)取代基的新喹啉羧酸衍生物及其制备方法 |
| JP2003171354A (ja) * | 2001-12-06 | 2003-06-20 | Daicel Chem Ind Ltd | 光学活性アミン化合物又はその塩の製造方法 |
| EP1882685A4 (en) * | 2005-05-20 | 2010-10-27 | Daiichi Sankyo Co Ltd | METHOD FOR PRODUCING AN ASYMMETRIC TETRASUBSTITUTED CARBON CONTAINING COMPOUND |
| CN103012198A (zh) * | 2011-09-21 | 2013-04-03 | 中国药科大学 | 光学活性环状化合物的制备方法 |
| KR200469128Y1 (ko) * | 2013-05-16 | 2013-09-25 | 김진란 | 첨가물의 수납부가 형성된 속뚜껑 |
| CN103435523B (zh) * | 2013-08-13 | 2015-12-23 | 苏州楚凯药业有限公司 | (1r，2s)-2-氟-环丙胺对甲苯磺酸盐的制备方法 |
| CN109956896B (zh) * | 2017-12-14 | 2021-03-12 | 中国医药集团总公司四川抗菌素工业研究所 | 一种螺[环丙烷-1,3-吲哚啉]骨架物及其晶体和其制备方法与用途 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2557220A1 (de) * | 1975-12-19 | 1977-06-23 | Goedecke Ag | N-substituierte spirolactame |
| CA1336090C (en) * | 1988-08-31 | 1995-06-27 | Isao Hayakawa | Spiro-substituted cyclic amines of quinolone derivatives |
| JP2964420B2 (ja) * | 1990-10-12 | 1999-10-18 | 第一製薬株式会社 | アザスピロヘプタン誘導体の塩 |
| JP3021109B2 (ja) * | 1991-05-17 | 2000-03-15 | 第一製薬株式会社 | アミノ化合物の製法 |
| JP3045574B2 (ja) * | 1991-05-17 | 2000-05-29 | 第一製薬株式会社 | アミノ化合物の製造法 |
| JP3432880B2 (ja) * | 1994-02-09 | 2003-08-04 | 第一製薬株式会社 | 光学活性アザスピロ化合物の製法 |
| JPH07233146A (ja) * | 1994-02-23 | 1995-09-05 | Dai Ichi Seiyaku Co Ltd | ラセミ化法 |
| JP3366723B2 (ja) * | 1994-04-18 | 2003-01-14 | 第一製薬株式会社 | 脱保護法 |
| JP3523921B2 (ja) * | 1994-12-09 | 2004-04-26 | 第一製薬株式会社 | アザスピロ誘導体およびその製造法 |
-
1996
- 1996-05-23 DE DE69622862T patent/DE69622862T2/de not_active Expired - Fee Related
- 1996-05-23 US US08/952,930 patent/US5856518A/en not_active Expired - Fee Related
- 1996-05-23 EA EA199700434A patent/EA000867B1/ru not_active IP Right Cessation
- 1996-05-23 EP EP96914415A patent/EP0829473B1/en not_active Expired - Lifetime
- 1996-05-23 CA CA002221946A patent/CA2221946C/en not_active Expired - Fee Related
- 1996-05-23 KR KR1019970708475A patent/KR100399512B1/ko not_active IP Right Cessation
- 1996-05-23 CN CNB01121015XA patent/CN1190421C/zh not_active Expired - Fee Related
- 1996-05-23 DK DK96914415T patent/DK0829473T3/da active
- 1996-05-23 EP EP01116855A patent/EP1148047A3/en not_active Withdrawn
- 1996-05-23 AU AU57789/96A patent/AU5778996A/en not_active Abandoned
- 1996-05-23 AT AT96914415T patent/ATE221876T1/de not_active IP Right Cessation
- 1996-05-23 CN CN96195656A patent/CN1080259C/zh not_active Expired - Fee Related
- 1996-05-23 ES ES96914415T patent/ES2181886T3/es not_active Expired - Lifetime
- 1996-05-23 WO PCT/JP1996/001373 patent/WO1996037470A1/ja active IP Right Grant
- 1996-05-23 PT PT96914415T patent/PT829473E/pt unknown
- 1996-05-24 TW TW085106264A patent/TW453986B/zh not_active IP Right Cessation
-
1997
- 1997-11-24 NO NO19975391A patent/NO316070B1/no unknown
-
1998
- 1998-07-09 US US09/112,379 patent/US6013806A/en not_active Expired - Fee Related
-
1999
- 1999-11-23 US US09/447,831 patent/US6218548B1/en not_active Expired - Fee Related
-
2003
- 2003-04-25 NO NO20031884A patent/NO324846B1/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO975391D0 (no) | 1997-11-24 |
| DE69622862D1 (de) | 2002-09-12 |
| CN1326930A (zh) | 2001-12-19 |
| EA199700434A1 (ru) | 1998-06-25 |
| CA2221946A1 (en) | 1996-11-28 |
| CN1191529A (zh) | 1998-08-26 |
| KR100399512B1 (ko) | 2004-03-30 |
| CN1190421C (zh) | 2005-02-23 |
| ES2181886T3 (es) | 2003-03-01 |
| US5856518A (en) | 1999-01-05 |
| NO20031884L (no) | 1998-01-26 |
| DK0829473T3 (da) | 2002-12-02 |
| TW453986B (en) | 2001-09-11 |
| WO1996037470A1 (fr) | 1996-11-28 |
| ATE221876T1 (de) | 2002-08-15 |
| NO324846B1 (no) | 2007-12-17 |
| AU5778996A (en) | 1996-12-11 |
| NO975391L (no) | 1998-01-26 |
| EA000867B1 (ru) | 2000-06-26 |
| EP0829473A1 (en) | 1998-03-18 |
| CN1080259C (zh) | 2002-03-06 |
| EP1148047A3 (en) | 2004-10-06 |
| PT829473E (pt) | 2002-11-29 |
| EP0829473A4 (en) | 1998-10-07 |
| CA2221946C (en) | 2005-03-15 |
| US6218548B1 (en) | 2001-04-17 |
| KR19990022000A (ko) | 1999-03-25 |
| EP1148047A2 (en) | 2001-10-24 |
| US6013806A (en) | 2000-01-11 |
| DE69622862T2 (de) | 2003-03-27 |
| NO20031884D0 (no) | 2003-04-25 |
| EP0829473B1 (en) | 2002-08-07 |
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