NO803835L - Fremgangsmaate for fremstilling av n-substiuerte alfa-aminosyrer - Google Patents

Fremgangsmaate for fremstilling av n-substiuerte alfa-aminosyrer

Info

Publication number: NO803835L
Authority: NO; Norway
Prior art keywords: formula; compound; respect; group; stated
Prior art date: 1979-12-19

Application number

NO803835A

Other languages

English (en)

Norwegian (no)

Inventor

Harry Ferres

Original Assignee

Beecham Group Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1979-12-19

Filing date

1980-12-17

Publication date

1981-06-22

1980-12-17 Application filed by Beecham Group Ltd filed Critical Beecham Group Ltd

1981-06-22 Publication of NO803835L publication Critical patent/NO803835L/no

Links

238000000034 method Methods 0.000 title claims description 18
238000002360 preparation method Methods 0.000 title claims description 17
150000001413 amino acids Chemical class 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 45
-1 methylenedioxy Chemical group 0.000 claims description 40
150000002148 esters Chemical class 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
230000000903 blocking effect Effects 0.000 claims description 8
239000003638 chemical reducing agent Substances 0.000 claims description 8
150000004678 hydrides Chemical class 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
125000004434 sulfur atom Chemical group 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
125000002619 bicyclic group Chemical group 0.000 claims description 3
150000001728 carbonyl compounds Chemical class 0.000 claims description 3
UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 2
125000006301 indolyl methyl group Chemical group 0.000 claims description 2
125000006239 protecting group Chemical group 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 1
239000002243 precursor Substances 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
239000002253 acid Substances 0.000 description 15
239000003814 drug Substances 0.000 description 14
229940079593 drug Drugs 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
239000000203 mixture Substances 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000002585 base Substances 0.000 description 9
229960005190 phenylalanine Drugs 0.000 description 8
239000000243 solution Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
239000003937 drug carrier Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
239000000126 substance Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 6
230000006181 N-acylation Effects 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
229940024606 amino acid Drugs 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 5
235000005911 diet Nutrition 0.000 description 5
230000037213 diet Effects 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 5
239000002904 solvent Substances 0.000 description 5
WSJWDFMOAQCHIG-UHFFFAOYSA-N 2-[(4-chlorophenyl)methylamino]-3-pyridin-2-ylpropanoic acid Chemical compound C=1C=C(Cl)C=CC=1CNC(C(=O)O)CC1=CC=CC=N1 WSJWDFMOAQCHIG-UHFFFAOYSA-N 0.000 description 4
AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 4
108010010234 HDL Lipoproteins Proteins 0.000 description 4
102000015779 HDL Lipoproteins Human genes 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000005917 acylation reaction Methods 0.000 description 4
235000001014 amino acid Nutrition 0.000 description 4
235000019441 ethanol Nutrition 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
230000010933 acylation Effects 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
210000002966 serum Anatomy 0.000 description 3
239000000600 sorbitol Substances 0.000 description 3
235000010356 sorbitol Nutrition 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
239000003826 tablet Substances 0.000 description 3
SAOHCSVJQIAGDD-OAHLLOKOSA-N (2r)-2-[(4-chlorophenyl)methylamino]-3-phenylpropanoic acid Chemical compound C([C@H](C(=O)O)NCC=1C=CC(Cl)=CC=1)C1=CC=CC=C1 SAOHCSVJQIAGDD-OAHLLOKOSA-N 0.000 description 2
AZFHRMJKXLRMAI-HNNXBMFYSA-N (2s)-2-[(4-chlorophenyl)methylamino]-3-(4-hydroxyphenyl)propanoic acid Chemical compound C([C@@H](C(=O)O)NCC=1C=CC(Cl)=CC=1)C1=CC=C(O)C=C1 AZFHRMJKXLRMAI-HNNXBMFYSA-N 0.000 description 2
OLLADMMPXBNPKQ-UHFFFAOYSA-N 2-[(4-chlorophenyl)methylazaniumyl]-3-(1h-indol-3-yl)propanoate Chemical compound C=1NC2=CC=CC=C2C=1CC(C(=O)O)NCC1=CC=C(Cl)C=C1 OLLADMMPXBNPKQ-UHFFFAOYSA-N 0.000 description 2
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
244000215068 Acacia senegal Species 0.000 description 2
235000006491 Acacia senegal Nutrition 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
229920000084 Gum arabic Polymers 0.000 description 2
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 2
108010007622 LDL Lipoproteins Proteins 0.000 description 2
102000007330 LDL Lipoproteins Human genes 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
108010062497 VLDL Lipoproteins Proteins 0.000 description 2
235000010489 acacia gum Nutrition 0.000 description 2
150000001371 alpha-amino acids Chemical class 0.000 description 2
235000008206 alpha-amino acids Nutrition 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
230000036765 blood level Effects 0.000 description 2
MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 2
239000002775 capsule Substances 0.000 description 2
235000012000 cholesterol Nutrition 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
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238000011049 filling Methods 0.000 description 2
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235000011852 gelatine desserts Nutrition 0.000 description 2
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XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000003791 organic solvent mixture Substances 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 2
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239000003755 preservative agent Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
WSJWDFMOAQCHIG-CQSZACIVSA-N (2R)-2-[(4-chlorophenyl)methylamino]-3-pyridin-2-ylpropanoic acid Chemical compound OC(=O)[C@@H](CC1=NC=CC=C1)NCC1=CC=C(Cl)C=C1 WSJWDFMOAQCHIG-CQSZACIVSA-N 0.000 description 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 1
XDAZZJZQPKVWHH-UHFFFAOYSA-N 2-[(4-chlorophenyl)methylamino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NCC1=CC=C(Cl)C=C1 XDAZZJZQPKVWHH-UHFFFAOYSA-N 0.000 description 1
YDWCQXDJOMSGDI-UHFFFAOYSA-N 2-[(4-chlorophenyl)methylamino]-3-pyridin-4-ylpropanoic acid Chemical compound C=1C=C(Cl)C=CC=1CNC(C(=O)O)CC1=CC=NC=C1 YDWCQXDJOMSGDI-UHFFFAOYSA-N 0.000 description 1
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UKVGOZPBEDOTQF-UHFFFAOYSA-N 2-amino-3-pyridin-2-ylpropanoic acid;hydrobromide Chemical compound Br.OC(=O)C(N)CC1=CC=CC=N1 UKVGOZPBEDOTQF-UHFFFAOYSA-N 0.000 description 1
PDRJLZDUOULRHE-UHFFFAOYSA-N 2-azaniumyl-3-pyridin-2-ylpropanoate Chemical compound OC(=O)C(N)CC1=CC=CC=N1 PDRJLZDUOULRHE-UHFFFAOYSA-N 0.000 description 1
125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 1
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239000005725 8-Hydroxyquinoline Substances 0.000 description 1
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QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
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239000004215 Carbon black (E152) Substances 0.000 description 1
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KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
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FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
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MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
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238000004809 thin layer chromatography Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- 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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Obesity (AREA)
Diabetes (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Hematology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pyridine Compounds (AREA)
Indole Compounds (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

NO803835A 1979-12-19 1980-12-17 Fremgangsmaate for fremstilling av n-substiuerte alfa-aminosyrer NO803835L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7943794		1979-12-19

Publications (1)

Publication Number	Publication Date
NO803835L true NO803835L (no)	1981-06-22

Family

ID=10509949

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO803835A NO803835L (no)	1979-12-19	1980-12-17	Fremgangsmaate for fremstilling av n-substiuerte alfa-aminosyrer

Country Status (9)

Country	Link
EP (1)	EP0031653A1 (es)
JP (1)	JPS5692843A (es)
AU (1)	AU6546780A (es)
DK (1)	DK541580A (es)
ES (4)	ES497907A0 (es)
GR (1)	GR72257B (es)
IL (1)	IL61675A0 (es)
NO (1)	NO803835L (es)
ZA (1)	ZA807795B (es)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0067641A3 (en) *	1981-06-17	1983-03-09	Beecham Group Plc	Amino acids
KR920701152A (ko) *	1988-11-14	1992-08-11	로버트 에이. 아미테이지	당뇨병, 비반증 및 동맥경화증 치료제로 유용한 알파-아미노-인돌-3-세트산
US5245046A (en) *	1988-11-14	1993-09-14	The Upjohn Company	α-amino-indole-3-acetic acids useful as anti-diabetic, anti-obesity and anti-atherosclerotic agents
EP0375133A1 (en) *	1988-11-14	1990-06-27	The Upjohn Company	Alpha-amino-indole-3-acetic acids useful as anti-diabetic, anti-obesity and anti-atherosclerotic agents
US5163131A (en) *	1989-09-08	1992-11-10	Auspex Systems, Inc.	Parallel i/o network file server architecture
KR101317947B1 (ko) *	2013-07-04	2013-10-16	이영우	실린더 검사장치

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3950542A (en) *	1967-02-21	1976-04-13	L'oreal	Cysteamine derivatives for oral treatment of seborrhea

1980
- 1980-12-05 EP EP80304407A patent/EP0031653A1/en not_active Ceased
- 1980-12-09 IL IL61675A patent/IL61675A0/xx unknown
- 1980-12-12 ZA ZA00807795A patent/ZA807795B/xx unknown
- 1980-12-17 NO NO803835A patent/NO803835L/no unknown
- 1980-12-17 AU AU65467/80A patent/AU6546780A/en not_active Abandoned
- 1980-12-18 DK DK541580A patent/DK541580A/da unknown
- 1980-12-18 GR GR63711A patent/GR72257B/el unknown
- 1980-12-18 ES ES497907A patent/ES497907A0/es active Granted
- 1980-12-19 JP JP18031880A patent/JPS5692843A/ja active Pending
1981
- 1981-12-11 ES ES507916A patent/ES507916A0/es active Granted
- 1981-12-11 ES ES507917A patent/ES8307205A1/es not_active Expired
- 1981-12-11 ES ES507915A patent/ES507915A0/es active Granted

Also Published As

Publication number	Publication date
ES507917A0 (es)	1982-11-01
IL61675A0 (en)	1981-01-30
GR72257B (es)	1983-10-06
ES8301460A1 (es)	1982-05-01
AU6546780A (en)	1981-06-25
ES8307205A1 (es)	1982-11-01
EP0031653A1 (en)	1981-07-08
DK541580A (da)	1981-06-20
JPS5692843A (en)	1981-07-27
ES8308302A1 (es)	1983-01-01
ZA807795B (en)	1982-01-27
ES8306096A1 (es)	1982-10-01
ES507915A0 (es)	1982-10-01
ES507916A0 (es)	1983-01-01
ES497907A0 (es)	1982-05-01

Publication	Publication Date	Title
US5672598A (en)	1997-09-30	Lactam-containing hydroxamic acids
CA1328333C (en)	1994-04-05	Amino acid derivatives
BE1006343A5 (fr)	1994-07-26	Derives de l'indole.
US9018258B2 (en)	2015-04-28	Substituted 1-benzylcycloalkylcarboxylic acids and the use thereof
Bey et al.	1978	Analogs of ornithine as inhibitors of ornithine decarboxylase. New deductions concerning the topography of the enzyme's active site
DE69522676T2 (de)	2002-04-18	Naphtalen-derivate als prostaglandin i2 agonisten
DE69005286T2 (de)	1994-04-21	Peptide mit tachykininantagonistischer Aktivität, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate.
FI78684B (fi)	1989-05-31	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara cis, endo-2-azabicyklo-/5.3.0/-dekan-3- karboxylsyraderivat och mellanprodukter.
JPH08511028A (ja)	1996-11-19	Ｐ物質拮抗剤としてのベンジルオキシキヌクリジン
JP2000516955A (ja)	2000-12-19	置換環状アミンメタロプロテアーゼ阻害剤
JPH05503719A (ja)	1993-06-17	ペプチジル誘導体
JPS6323186B2 (es)	1988-05-16
JP2000516252A (ja)	2000-12-05	１，４―複素環式メタロプロテアーゼ阻害剤
IE51918B1 (en)	1987-04-29	Bicyclic compounds their production and use
RU2212404C2 (ru)	2003-09-20	Производные индола и фармацевтические композиции, включающие их
SU1241986A3 (ru)	1986-06-30	Способ получени производных бензамида,их гидрохлоридов или оптических изомеров
JPH08505375A (ja)	1996-06-11	置換基をもつトリオール類
US4443464A (en)	1984-04-17	(+)-2-[1-(2,6-Dichlorophenoxy)-ethyl]-1,3-diazacyclopent-2-ene and the method for the treatment of human beings suffering from nervous disarrangements, in particular migraine
TW200524578A (en)	2005-08-01	Protease inhibitors
EP0787716B1 (en)	1999-12-08	Isoprene derivatives
US6110933A (en)	2000-08-29	Amino acid derivatives and their use as phospholipase A2 inhibitor
JPWO1994001392A1 (ja)	1994-06-02	（−）−リトドリン
KR950006891B1 (ko)	1995-06-26	아미노 알코올의 제조방법
DE69231350T2 (de)	2001-01-04	Indolizinderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen
JPH05504970A (ja)	1993-07-29	尿素誘導体類、それらの製造およびそれらを含有している薬用生成物