DE3879622T2 - Aminopimelinsäure-Derivate, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel. - Google Patents
Aminopimelinsäure-Derivate, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel.Info
- Publication number
- DE3879622T2 DE3879622T2 DE88402741T DE3879622T DE3879622T2 DE 3879622 T2 DE3879622 T2 DE 3879622T2 DE 88402741 T DE88402741 T DE 88402741T DE 3879622 T DE3879622 T DE 3879622T DE 3879622 T2 DE3879622 T2 DE 3879622T2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- carbon atoms
- acid
- radical
- amino
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Fee Related
Links
- 239000003814 drug Substances 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 7
- 230000008569 process Effects 0.000 title claims description 7
- 229940079593 drug Drugs 0.000 title abstract description 4
- JUQLUIFNNFIIKC-UHFFFAOYSA-N 2-aminopimelic acid Chemical class OC(=O)C(N)CCCCC(O)=O JUQLUIFNNFIIKC-UHFFFAOYSA-N 0.000 title description 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 55
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- -1 substituted alkyl radical Chemical class 0.000 claims abstract description 38
- 239000002253 acid Substances 0.000 claims abstract description 33
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 235000001014 amino acid Nutrition 0.000 claims abstract description 22
- 150000001413 amino acids Chemical group 0.000 claims abstract description 22
- 150000002148 esters Chemical class 0.000 claims abstract description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 150000003254 radicals Chemical class 0.000 claims abstract description 15
- 150000001298 alcohols Chemical class 0.000 claims abstract description 13
- 150000003140 primary amides Chemical class 0.000 claims abstract description 13
- 150000003334 secondary amides Chemical class 0.000 claims abstract description 13
- 150000001412 amines Chemical class 0.000 claims abstract description 10
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000007524 organic acids Chemical class 0.000 claims abstract description 6
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims abstract description 5
- 235000004279 alanine Nutrition 0.000 claims abstract description 5
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 37
- 239000002585 base Substances 0.000 claims description 24
- 150000007513 acids Chemical class 0.000 claims description 20
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 239000011707 mineral Substances 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 230000007062 hydrolysis Effects 0.000 claims description 12
- 238000006460 hydrolysis reaction Methods 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- 230000009471 action Effects 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 9
- 239000004472 Lysine Substances 0.000 claims description 8
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims description 8
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 230000009435 amidation Effects 0.000 claims description 6
- 238000007112 amidation reaction Methods 0.000 claims description 6
- RSELGJIRXXSQRO-UHFFFAOYSA-N (R,E)-2-Amino-3-heptenedioic acid Natural products OC(=O)C(N)C=CCCC(O)=O RSELGJIRXXSQRO-UHFFFAOYSA-N 0.000 claims description 5
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 238000006114 decarboxylation reaction Methods 0.000 claims description 5
- 230000032050 esterification Effects 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 230000009467 reduction Effects 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 101150058891 alc1 gene Proteins 0.000 claims description 4
- 101150117093 alc2 gene Proteins 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 238000003776 cleavage reaction Methods 0.000 claims description 4
- 230000007017 scission Effects 0.000 claims description 4
- ITWPXILLCCAJBT-PKPIPKONSA-N 6-[[(2s)-2-aminopropanoyl]amino]hept-3-enedioic acid Chemical compound C[C@H](N)C(=O)NC(C(O)=O)CC=CCC(O)=O ITWPXILLCCAJBT-PKPIPKONSA-N 0.000 claims description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- NUYLDWMFACSJSP-PKPIPKONSA-N 2-[[(2s)-2-aminopropanoyl]amino]hept-3-enedioic acid Chemical compound C[C@H](N)C(=O)NC(C(O)=O)C=CCCC(O)=O NUYLDWMFACSJSP-PKPIPKONSA-N 0.000 claims description 2
- MYQSWZLILUHUJN-RGURZIINSA-N 6-[[(2s)-2,6-diaminohexanoyl]amino]hept-3-enedioic acid Chemical compound NCCCC[C@H](N)C(=O)NC(C(O)=O)CC=CCC(O)=O MYQSWZLILUHUJN-RGURZIINSA-N 0.000 claims description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 2
- 238000010511 deprotection reaction Methods 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims 1
- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 230000000911 decarboxylating effect Effects 0.000 claims 1
- 150000004767 nitrides Chemical class 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 abstract description 2
- 238000002483 medication Methods 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 132
- 239000000047 product Substances 0.000 description 125
- 239000000243 solution Substances 0.000 description 62
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
- 239000000203 mixture Substances 0.000 description 52
- 229910001868 water Inorganic materials 0.000 description 51
- 238000003756 stirring Methods 0.000 description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000000377 silicon dioxide Substances 0.000 description 30
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 29
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical group CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 20
- 239000012267 brine Substances 0.000 description 20
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical group OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 20
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 229940024606 amino acid Drugs 0.000 description 12
- 239000012043 crude product Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 235000017557 sodium bicarbonate Nutrition 0.000 description 12
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 11
- 102000000589 Interleukin-1 Human genes 0.000 description 11
- 108010002352 Interleukin-1 Proteins 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical group [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 10
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 10
- 229910021529 ammonia Inorganic materials 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 10
- 238000004587 chromatography analysis Methods 0.000 description 10
- 102000003390 tumor necrosis factor Human genes 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 125000003412 L-alanyl group Chemical group [H]N([H])[C@@](C([H])([H])[H])(C(=O)[*])[H] 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
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- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 9
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- 235000012239 silicon dioxide Nutrition 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 8
- 239000005977 Ethylene Substances 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 235000011054 acetic acid Nutrition 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- OXQWBLJQOBXJPM-UHFFFAOYSA-N hept-2-enedioic acid Chemical group OC(=O)CCCC=CC(O)=O OXQWBLJQOBXJPM-UHFFFAOYSA-N 0.000 description 8
- 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 7
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 7
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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- TYEYBOSBBBHJIV-UHFFFAOYSA-M 2-oxobutanoate Chemical compound CCC(=O)C([O-])=O TYEYBOSBBBHJIV-UHFFFAOYSA-M 0.000 description 2
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- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- JOYQIVSIQHTMLC-UHFFFAOYSA-N cyclohexene;ethyl acetate Chemical compound CCOC(C)=O.C1CCC=CC1 JOYQIVSIQHTMLC-UHFFFAOYSA-N 0.000 description 1
- LYBCHMBMGSZNOA-UHFFFAOYSA-N dichloromethane;formic acid;methanol Chemical compound OC.OC=O.ClCCl LYBCHMBMGSZNOA-UHFFFAOYSA-N 0.000 description 1
- YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 1
- IUBDICUSSWWKHO-UHFFFAOYSA-N diethyl 2-formamido-2-(2-methylprop-2-enyl)propanedioate Chemical compound CCOC(=O)C(CC(C)=C)(NC=O)C(=O)OCC IUBDICUSSWWKHO-UHFFFAOYSA-N 0.000 description 1
- UPQZOUHVTJNGFK-UHFFFAOYSA-N diethyl 2-methylpropanedioate Chemical compound CCOC(=O)C(C)C(=O)OCC UPQZOUHVTJNGFK-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Chemical compound CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012154 double-distilled water Substances 0.000 description 1
- 230000009982 effect on human Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
- SHBZIVGPMJCDGD-UHFFFAOYSA-N ethyl 2-(methoxycarbonylamino)-2,4-dimethylpent-4-enoate Chemical compound CCOC(=O)C(C)(CC(C)=C)NC(=O)OC SHBZIVGPMJCDGD-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 125000002642 gamma-glutamyl group Chemical group 0.000 description 1
- 235000020664 gamma-linolenic acid Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 208000007475 hemolytic anemia Diseases 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000000642 iatrogenic effect Effects 0.000 description 1
- 229960001438 immunostimulant agent Drugs 0.000 description 1
- 239000003022 immunostimulating agent Substances 0.000 description 1
- 230000003308 immunostimulating effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 201000002364 leukopenia Diseases 0.000 description 1
- 231100001022 leukopenia Toxicity 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- GMKMEZVLHJARHF-SYDPRGILSA-N meso-2,6-diaminopimelic acid Chemical compound [O-]C(=O)[C@@H]([NH3+])CCC[C@@H]([NH3+])C([O-])=O GMKMEZVLHJARHF-SYDPRGILSA-N 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000003226 mitogen Substances 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- HYIDEDUTFDYUHM-UHFFFAOYSA-N n-dimethylsulfinamoyl-n-methylmethanamine Chemical compound CN(C)S(=O)N(C)C HYIDEDUTFDYUHM-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 208000030428 polyarticular arthritis Diseases 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 206010036784 proctocolitis Diseases 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 101150018444 sub2 gene Proteins 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 206010043778 thyroiditis Diseases 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- UEEQYOVGXKCSFV-UHFFFAOYSA-N triethyl 1-formamido-3-methylidenepentane-1,1,5-tricarboxylate Chemical compound CCOC(=O)CCC(=C)CC(NC=O)(C(=O)OCC)C(=O)OCC UEEQYOVGXKCSFV-UHFFFAOYSA-N 0.000 description 1
- IJZUCRYQGXEMLO-UHFFFAOYSA-N triethyl 1-formamidopent-2-ene-1,1,5-tricarboxylate Chemical compound CCOC(=O)CCC=CC(NC=O)(C(=O)OCC)C(=O)OCC IJZUCRYQGXEMLO-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
- C07K1/08—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using activating agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Oncology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Communicable Diseases (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Virology (AREA)
- Hematology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
- Saccharide Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8715209A FR2622578B1 (fr) | 1987-11-03 | 1987-11-03 | Nouveaux derives de l'acide aminopimelique, leur procede de preparation et leur application comme medicaments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3879622D1 DE3879622D1 (de) | 1993-04-29 |
| DE3879622T2 true DE3879622T2 (de) | 1993-09-30 |
Family
ID=9356421
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE88402741T Expired - Fee Related DE3879622T2 (de) | 1987-11-03 | 1988-11-02 | Aminopimelinsäure-Derivate, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5030715A (enExample) |
| EP (1) | EP0315519B1 (enExample) |
| JP (1) | JPH01151543A (enExample) |
| AT (1) | ATE87299T1 (enExample) |
| AU (1) | AU615229B2 (enExample) |
| CA (1) | CA1310445C (enExample) |
| DE (1) | DE3879622T2 (enExample) |
| DK (1) | DK607688A (enExample) |
| ES (1) | ES2053787T3 (enExample) |
| FR (1) | FR2622578B1 (enExample) |
| GR (1) | GR3007597T3 (enExample) |
| HU (1) | HU202471B (enExample) |
| MX (1) | MX173858B (enExample) |
| PT (1) | PT88926B (enExample) |
| ZA (1) | ZA888200B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6077915A (en) * | 1990-07-23 | 2000-06-20 | Exxon Research & Engineering | Carbonyl containing compounds |
| WO2001051474A2 (en) * | 2000-01-11 | 2001-07-19 | Biostream Therapeutics, Inc. | Polypharmacophoric agents |
| CN113072456B (zh) * | 2021-04-12 | 2022-04-19 | 中国科学技术大学 | 一种手性α-二氟甲基氨基酸类化合物及其制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2566410A1 (fr) * | 1984-06-20 | 1985-12-27 | Delalande Sa | Nouveaux derives de l'acide diaminopimelique, leur procede de preparation et leur application en therapeutique |
-
1987
- 1987-11-03 FR FR8715209A patent/FR2622578B1/fr not_active Expired - Fee Related
-
1988
- 1988-11-01 MX MX013643A patent/MX173858B/es unknown
- 1988-11-01 DK DK607688A patent/DK607688A/da not_active Application Discontinuation
- 1988-11-02 EP EP88402741A patent/EP0315519B1/fr not_active Expired - Lifetime
- 1988-11-02 AU AU24582/88A patent/AU615229B2/en not_active Ceased
- 1988-11-02 HU HU885678A patent/HU202471B/hu not_active IP Right Cessation
- 1988-11-02 AT AT88402741T patent/ATE87299T1/de not_active IP Right Cessation
- 1988-11-02 DE DE88402741T patent/DE3879622T2/de not_active Expired - Fee Related
- 1988-11-02 JP JP63276337A patent/JPH01151543A/ja active Pending
- 1988-11-02 ES ES88402741T patent/ES2053787T3/es not_active Expired - Lifetime
- 1988-11-02 ZA ZA888200A patent/ZA888200B/xx unknown
- 1988-11-02 CA CA000581930A patent/CA1310445C/fr not_active Expired - Lifetime
- 1988-11-03 PT PT88926A patent/PT88926B/pt not_active IP Right Cessation
- 1988-11-03 US US07/267,190 patent/US5030715A/en not_active Expired - Fee Related
-
1993
- 1993-04-09 GR GR920402861T patent/GR3007597T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GR3007597T3 (enExample) | 1993-08-31 |
| AU2458288A (en) | 1989-05-25 |
| PT88926B (pt) | 1993-01-29 |
| EP0315519A3 (en) | 1990-02-28 |
| ZA888200B (en) | 1990-01-31 |
| FR2622578B1 (fr) | 1990-03-16 |
| DK607688A (da) | 1989-06-20 |
| ES2053787T3 (es) | 1994-08-01 |
| DK607688D0 (da) | 1988-11-01 |
| MX13643A (es) | 1993-09-01 |
| EP0315519A2 (fr) | 1989-05-10 |
| US5030715A (en) | 1991-07-09 |
| CA1310445C (fr) | 1992-11-17 |
| HU202471B (en) | 1991-03-28 |
| ATE87299T1 (de) | 1993-04-15 |
| AU615229B2 (en) | 1991-09-26 |
| PT88926A (pt) | 1988-12-01 |
| FR2622578A1 (fr) | 1989-05-05 |
| HUT48568A (en) | 1989-06-28 |
| DE3879622D1 (de) | 1993-04-29 |
| JPH01151543A (ja) | 1989-06-14 |
| MX173858B (es) | 1994-04-07 |
| EP0315519B1 (fr) | 1993-03-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |