DD269148A5 - Verfahren zur herstellung von 5-amino-4-hydroxy-valeriansaeure-derivaten - Google Patents

Verfahren zur herstellung von 5-amino-4-hydroxy-valeriansaeure-derivaten Download PDF

Info

Publication number: DD269148A5
Authority: DD; German Democratic Republic
Prior art keywords: lower alkyl; formula; acid; cycloalkyl; amino
Prior art date: 1986-08-13

Application number

DD87305909A

Other languages

German (de)

English (en)

Inventor

Peter Herold

Christof Angst

Original Assignee

��@��@��k��

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.)

1986-08-13

Filing date

1987-08-11

Publication date

1989-06-21

1987-08-11 Application filed by ��@��@��k�� filed Critical ��@��@��k��

1989-06-21 Publication of DD269148A5 publication Critical patent/DD269148A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 47
230000008569 process Effects 0.000 title claims abstract description 31
238000002360 preparation method Methods 0.000 title claims abstract description 30
-1 amino, hydroxy, mercapto, sulfinyl Chemical group 0.000 claims abstract description 247
125000000217 alkyl group Chemical group 0.000 claims abstract description 159
150000001875 compounds Chemical class 0.000 claims abstract description 157
239000002253 acid Substances 0.000 claims abstract description 72
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 47
239000001257 hydrogen Substances 0.000 claims abstract description 46
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 46
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 45
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 38
125000003118 aryl group Chemical group 0.000 claims abstract description 35
229910052736 halogen Inorganic materials 0.000 claims abstract description 29
150000002367 halogens Chemical class 0.000 claims abstract description 28
125000003277 amino group Chemical group 0.000 claims abstract description 22
150000002431 hydrogen Chemical class 0.000 claims abstract description 22
125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 17
150000001413 amino acids Chemical class 0.000 claims abstract description 16
150000002596 lactones Chemical group 0.000 claims abstract description 15
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 64
238000006243 chemical reaction Methods 0.000 claims description 53
150000003839 salts Chemical class 0.000 claims description 53
150000002148 esters Chemical class 0.000 claims description 31
125000003545 alkoxy group Chemical group 0.000 claims description 24
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 24
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
125000003282 alkyl amino group Chemical group 0.000 claims description 23
239000003054 catalyst Substances 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 18
125000003396 thiol group Chemical class [H]S* 0.000 claims description 18
239000004215 Carbon black (E152) Substances 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
125000006239 protecting group Chemical group 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 16
229930195733 hydrocarbon Natural products 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
229910052799 carbon Inorganic materials 0.000 claims description 14
239000003795 chemical substances by application Substances 0.000 claims description 13
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 11
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 8
NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
101150065749 Churc1 gene Proteins 0.000 claims description 8
102100038239 Protein Churchill Human genes 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
125000004414 alkyl thio group Chemical group 0.000 claims description 6
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
230000002140 halogenating effect Effects 0.000 claims description 6
125000004423 acyloxy group Chemical group 0.000 claims description 5
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 5
238000000926 separation method Methods 0.000 claims description 5
OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 4
125000001072 heteroaryl group Chemical group 0.000 claims description 4
238000011065 in-situ storage Methods 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
125000004185 ester group Chemical group 0.000 claims description 3
125000005236 alkanoylamino group Chemical group 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
150000003857 carboxamides Chemical group 0.000 claims description 2
125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000002911 monocyclic heterocycle group Chemical group 0.000 claims 2
239000002243 precursor Substances 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 10
TYMZJFJDBQLYHB-UHFFFAOYSA-N 5-amino-4-hydroxypentanoic acid Chemical class NCC(O)CCC(O)=O TYMZJFJDBQLYHB-UHFFFAOYSA-N 0.000 abstract description 8
230000008707 rearrangement Effects 0.000 abstract description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 5
239000002461 renin inhibitor Substances 0.000 abstract description 5
229940086526 renin-inhibitors Drugs 0.000 abstract description 5
239000007858 starting material Substances 0.000 abstract description 5
238000007245 halolactonization reaction Methods 0.000 abstract description 4
239000012038 nucleophile Substances 0.000 abstract description 3
238000007142 ring opening reaction Methods 0.000 abstract description 3
230000003276 anti-hypertensive effect Effects 0.000 abstract description 2
150000003254 radicals Chemical class 0.000 description 60
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 50
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 38
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
238000005160 1H NMR spectroscopy Methods 0.000 description 32
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 25
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 24
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
239000002904 solvent Substances 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
239000003153 chemical reaction reagent Substances 0.000 description 20
125000004453 alkoxycarbonyl group Chemical group 0.000 description 19
239000002585 base Substances 0.000 description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 17
229910052794 bromium Inorganic materials 0.000 description 17
125000002252 acyl group Chemical group 0.000 description 15
150000001540 azides Chemical class 0.000 description 15
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 15
239000000460 chlorine Substances 0.000 description 15
238000006722 reduction reaction Methods 0.000 description 15
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
230000009467 reduction Effects 0.000 description 14
229940024606 amino acid Drugs 0.000 description 13
229910052801 chlorine Inorganic materials 0.000 description 13
230000032050 esterification Effects 0.000 description 13
238000005886 esterification reaction Methods 0.000 description 13
125000000524 functional group Chemical group 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 12
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 12
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 12
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
235000001014 amino acid Nutrition 0.000 description 12
125000002947 alkylene group Chemical group 0.000 description 11
150000001412 amines Chemical class 0.000 description 11
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
150000001408 amides Chemical class 0.000 description 10
125000004429 atom Chemical group 0.000 description 10
239000000047 product Substances 0.000 description 10
239000011734 sodium Substances 0.000 description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
230000002378 acidificating effect Effects 0.000 description 9
229910052783 alkali metal Inorganic materials 0.000 description 9
239000012267 brine Substances 0.000 description 9
150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 9
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
229910052717 sulfur Inorganic materials 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
150000001735 carboxylic acids Chemical class 0.000 description 8
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
XYPCFYDZWKTHRT-UHFFFAOYSA-N 1-cyclohexylbut-3-en-2-ol Chemical compound C=CC(O)CC1CCCCC1 XYPCFYDZWKTHRT-UHFFFAOYSA-N 0.000 description 7
229960000583 acetic acid Drugs 0.000 description 7
150000007513 acids Chemical class 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
239000012442 inert solvent Substances 0.000 description 7
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 7
229910052740 iodine Inorganic materials 0.000 description 7
108090000765 processed proteins & peptides Proteins 0.000 description 7
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
239000004471 Glycine Substances 0.000 description 6
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 6
LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 6
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 6
238000003776 cleavage reaction Methods 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
230000000269 nucleophilic effect Effects 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 6
239000002798 polar solvent Substances 0.000 description 6
230000007017 scission Effects 0.000 description 6
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 6
238000005809 transesterification reaction Methods 0.000 description 6
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
239000003513 alkali Substances 0.000 description 5
150000001340 alkali metals Chemical class 0.000 description 5
229910052784 alkaline earth metal Inorganic materials 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
150000003863 ammonium salts Chemical class 0.000 description 5
150000008064 anhydrides Chemical class 0.000 description 5
125000001309 chloro group Chemical group Cl* 0.000 description 5
239000011630 iodine Substances 0.000 description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 5
102000004196 processed proteins & peptides Human genes 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
239000011877 solvent mixture Substances 0.000 description 5
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 4
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
125000001246 bromo group Chemical group Br* 0.000 description 4
239000003638 chemical reducing agent Substances 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
125000006622 cycloheptylmethyl group Chemical group 0.000 description 4
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 4
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
229910052744 lithium Inorganic materials 0.000 description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000003791 organic solvent mixture Substances 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
239000010936 titanium Substances 0.000 description 4
229910052719 titanium Inorganic materials 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
DUAJIKVIRGATIW-UHFFFAOYSA-N trinitrogen(.) Chemical compound [N]=[N+]=[N-] DUAJIKVIRGATIW-UHFFFAOYSA-N 0.000 description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
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OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
KPNBUPJZFJCCIQ-LURJTMIESA-N methyl L-lysinate Chemical compound COC(=O)[C@@H](N)CCCCN KPNBUPJZFJCCIQ-LURJTMIESA-N 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
150000003956 methylamines Chemical class 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
UULXSTDDDXOTIY-UHFFFAOYSA-N n-iodoacetamide Chemical compound CC(=O)NI UULXSTDDDXOTIY-UHFFFAOYSA-N 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
150000002815 nickel Chemical class 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002829 nitrogen Chemical group 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
239000012434 nucleophilic reagent Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
125000005543 phthalimide group Chemical class 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
DOQQTKLDEQSKIE-UHFFFAOYSA-N silver;isocyanate Chemical compound [Ag+].[N-]=C=O DOQQTKLDEQSKIE-UHFFFAOYSA-N 0.000 description 1
238000006884 silylation reaction Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
239000011775 sodium fluoride Substances 0.000 description 1
235000013024 sodium fluoride Nutrition 0.000 description 1
PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Inorganic materials [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
PRWXGRGLHYDWPS-UHFFFAOYSA-L sodium malonate Chemical compound [Na+].[Na+].[O-]C(=O)CC([O-])=O PRWXGRGLHYDWPS-UHFFFAOYSA-L 0.000 description 1
239000004328 sodium tetraborate Substances 0.000 description 1
235000010339 sodium tetraborate Nutrition 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003459 sulfonic acid esters Chemical class 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 1
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
GMRIOAVKKGNMMV-UHFFFAOYSA-N tetrabutylazanium;azide Chemical compound [N-]=[N+]=[N-].CCCC[N+](CCCC)(CCCC)CCCC GMRIOAVKKGNMMV-UHFFFAOYSA-N 0.000 description 1
PEFQHPVDKJBRFF-UHFFFAOYSA-M tetrabutylazanium;cyanate Chemical compound [O-]C#N.CCCC[N+](CCCC)(CCCC)CCCC PEFQHPVDKJBRFF-UHFFFAOYSA-M 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
229960004319 trichloroacetic acid Drugs 0.000 description 1
125000000169 tricyclic heterocycle group Chemical group 0.000 description 1
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
239000012588 trypsin Substances 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
239000004474 valine Substances 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
239000008096 xylene Substances 0.000 description 1
125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/26—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S530/00—Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
- Y10S530/86—Renin inhibitors

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Peptides Or Proteins (AREA)
Furan Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

DD87305909A 1986-08-13 1987-08-11 Verfahren zur herstellung von 5-amino-4-hydroxy-valeriansaeure-derivaten DD269148A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH324886		1986-08-13

Publications (1)

Publication Number	Publication Date
DD269148A5 true DD269148A5 (de)	1989-06-21

Family

ID=4251859

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87305909A DD269148A5 (de)	1986-08-13	1987-08-11	Verfahren zur herstellung von 5-amino-4-hydroxy-valeriansaeure-derivaten

Country Status (14)

Country	Link
US (2)	US4898977A (fr)
EP (1)	EP0258183B1 (fr)
JP (1)	JP2571230B2 (fr)
KR (1)	KR950013635B1 (fr)
AT (1)	ATE86971T1 (fr)
DD (1)	DD269148A5 (fr)
DE (1)	DE3784812D1 (fr)
DK (1)	DK420887A (fr)
ES (1)	ES2053582T3 (fr)
FI (1)	FI90762C (fr)
HU (3)	HU200981B (fr)
IL (1)	IL83497A (fr)
MX (1)	MX7727A (fr)
PT (1)	PT85520B (fr)

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AU629867B2 (en) *	1988-11-17	1992-10-15	Imperial Chemical Industries Plc	Triazolo (4,3a) pyrazine derivatives
GB8912659D0 (en) *	1989-06-02	1989-07-19	Ici Plc	Process
GB8927915D0 (en) *	1989-12-11	1990-02-14	Hoffmann La Roche	Novel alcohols
DE4008403A1 (de) *	1990-03-16	1991-09-19	Merck Patent Gmbh	Glykolsaeurederivate
US5436339A (en) *	1991-03-06	1995-07-25	Abbott Laboratories	Process for the preparation of a substituted diaminoalcohol
EP0546230A1 (fr) *	1991-12-10	1993-06-16	Merrell Dow Pharmaceuticals Inc.	Nouveau procédé pour la préparation de l'acide 4-amino 5-hexénoique
US5294737A (en) *	1992-02-27	1994-03-15	The Research Foundation State University Of New York	Process for the production of chiral hydroxy-β-lactams and hydroxyamino acids derived therefrom
AU688403B2 (en) *	1993-11-03	1998-03-12	Commonwealth Scientific And Industrial Research Organisation	Allylic chain transfer agents
US5977278A (en) *	1993-11-03	1999-11-02	E. I. Du Pont De Nemours And Company	Polymers formed from allylic chain transfer agents
IL111484A (en) *	1993-11-03	2001-06-14	Commw Scient Ind Res Org	Polymerization process using pendant chain transfer means to regulate the molecular weight, the polymers thus obtained and a number of new pesticide compounds
US5475138A (en) *	1994-07-07	1995-12-12	Pharm-Eco Laboratories Incorporated	Method preparing amino acid-derived diaminopropanols
US5473104A (en) *	1994-09-13	1995-12-05	Neurocrine Biosciences, Inc.	Process for the preparation of L-carnitine
US5760019A (en) *	1996-07-12	1998-06-02	The Research Foundation Of State University Of New York	Silanol enzyme inhibitors
US6423850B1 (en)	1999-06-18	2002-07-23	E.I. Du Pont De Nemours And Company	Preparation and use of gamma-butyrolactones as cross-linking agents
US6833460B2 (en) *	1999-06-18	2004-12-21	E. I. Du Pont De Nemours And Company	Preparation and use of gamma-butyrolactones as cross-linking agents
US7314953B2 (en) *	2001-03-27	2008-01-01	Errant Gene Therapeutics, Llc	Treatment of lung cells with histone deacetylase inhibitors
US7842727B2 (en) *	2001-03-27	2010-11-30	Errant Gene Therapeutics, Llc	Histone deacetylase inhibitors
US8026280B2 (en) *	2001-03-27	2011-09-27	Errant Gene Therapeutics, Llc	Histone deacetylase inhibitors
US7312247B2 (en) *	2001-03-27	2007-12-25	Errant Gene Therapeutics, Llc	Histone deacetylase inhibitors
EP1511477A4 (fr) *	2002-05-22	2008-04-09	Errant Gene Therapeutics Llc	Inhibiteurs d'histone desacetylase bases sur des composes alpha-ceto-epoxydes
US20060160902A1 (en) *	2004-11-08	2006-07-20	Wiech Norbert L	Histone deacetylase inhibitors
CN101160281A (zh) *	2005-04-06	2008-04-09	特瓦制药工业有限公司	结晶形态的普瑞巴林
US7488846B2 (en) *	2005-04-11	2009-02-10	Teva Pharmaceuical Industries Ltd.	Pregabalin free of lactam and a process for preparation thereof
EP1768950A2 (fr) *	2005-04-11	2007-04-04	Teva Pharmaceutical Industries Ltd.	Procede de fabrication de (s)-pregabaline
DE602006017995D1 (de) *	2005-05-10	2010-12-16	Teva Pharma	Verfahren zur herstellung von pregabalin und salzen daraus
WO2006122255A1 (fr) *	2005-05-10	2006-11-16	Teva Pharmaceutical Industries Ltd.	Pregabaline exempte d'acide isobutylglutarique et son procede de preparation
US20070043241A1 (en) *	2005-05-10	2007-02-22	Lilach Hedvati	Optical resolution of 3-carbamoylmethyl-5-methylhexanoic acid
ES2398579T3 (es) *	2005-09-19	2013-03-20	Teva Pharmaceutical Industries Ltd	Una síntesis asimétrica de ácido (S)-(+)-3-(aminometil)-5-metilhexanoico
WO2007139933A2 (fr) *	2006-05-24	2007-12-06	Teva Pharmaceutical Industries Ltd.	Procédés pour la préparation d'acide r-(+)-3-(carbamoyl méthyl)-5-méthylhexanoïque et de sels de celui-ci
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1987
- 1987-08-07 ES ES87810450T patent/ES2053582T3/es not_active Expired - Lifetime
- 1987-08-07 EP EP87810450A patent/EP0258183B1/fr not_active Expired - Lifetime
- 1987-08-07 DE DE8787810450T patent/DE3784812D1/de not_active Expired - Fee Related
- 1987-08-07 AT AT87810450T patent/ATE86971T1/de not_active IP Right Cessation
- 1987-08-10 FI FI873467A patent/FI90762C/fi not_active IP Right Cessation
- 1987-08-11 IL IL83497A patent/IL83497A/xx unknown
- 1987-08-11 PT PT85520A patent/PT85520B/pt not_active IP Right Cessation
- 1987-08-11 DD DD87305909A patent/DD269148A5/de not_active IP Right Cessation
- 1987-08-12 DK DK420887A patent/DK420887A/da not_active Application Discontinuation
- 1987-08-12 MX MX772787A patent/MX7727A/es unknown
- 1987-08-12 JP JP62200085A patent/JP2571230B2/ja not_active Expired - Lifetime
- 1987-08-12 HU HU883005A patent/HU200981B/hu not_active IP Right Cessation
- 1987-08-12 KR KR1019870008819A patent/KR950013635B1/ko not_active Expired - Fee Related
- 1987-08-12 HU HU873654A patent/HU198445B/hu not_active IP Right Cessation
- 1987-08-12 HU HU883004A patent/HU202218B/hu not_active IP Right Cessation
- 1987-08-13 US US07/085,437 patent/US4898977A/en not_active Expired - Fee Related
1989
- 1989-10-24 US US07/426,927 patent/US5010189A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DK420887A (da)	1988-02-14
KR880002808A (ko)	1988-05-11
ATE86971T1 (de)	1993-04-15
US5010189A (en)	1991-04-23
DE3784812D1 (de)	1993-04-22
JP2571230B2 (ja)	1997-01-16
EP0258183A3 (en)	1989-07-26
JPS6357561A (ja)	1988-03-12
PT85520A (en)	1987-09-01
IL83497A (en)	1993-02-21
HUT44478A (en)	1988-03-28
FI873467A7 (fi)	1988-02-14
EP0258183A2 (fr)	1988-03-02
PT85520B (pt)	1990-06-29
HU198445B (en)	1989-10-30
HU200981B (en)	1990-09-28
MX7727A (es)	1993-12-01
ES2053582T3 (es)	1994-08-01
FI90762B (fi)	1993-12-15
KR950013635B1 (ko)	1995-11-13
EP0258183B1 (fr)	1993-03-17
IL83497A0 (en)	1988-01-31
FI90762C (fi)	1994-03-25
DK420887D0 (da)	1987-08-12
FI873467A0 (fi)	1987-08-10
US4898977A (en)	1990-02-06
HU202218B (en)	1991-02-28

Legal Events

Date	Code	Title	Description
2000-02-17	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD269148A5 (de)	1989-06-21	Verfahren zur herstellung von 5-amino-4-hydroxy-valeriansaeure-derivaten
EP0184550B1 (fr)	1992-03-18	Dérivés de 5-amino-4-hydroxy valérylamides
Evans et al.	1985	A stereocontrolled synthesis of hydroxyethylene dipeptide isosteres using novel, chiral aminoalkyl epoxides and. gamma.-(aminoalkyl)-. gamma.-lactones
EP0400290A1 (fr)	1990-12-05	Dérivés de l'acide 5-amino-4-hydroxyvalérique utilisables en tant qu'intermédiaires dans la synthèse d'inhibiteurs de la rénine
EP0236734A2 (fr)	1987-09-16	Dérivés d'amino-5-hydroxy-4-valeryl substitués par des groupes contenant du soufre
DE69503904T2 (de)	1999-04-22	Phosphinsaeurederivate mit metallopeptidase inhibtorischer wirkung
EP0374098A2 (fr)	1990-06-20	Inhibiteurs de protéase rétrovirale
EP0271795A2 (fr)	1988-06-22	Dérivés de l'octahydro-10-oxo-6H-pyridazo[1,2-a][112]diazépine, intermédiaires et procédé pour leur préparation ainsi que médicament les contenant
EP0144290A2 (fr)	1985-06-12	Dérivés éthylènediamine substitués
DE60131733T2 (de)	2008-10-30	Verfahren zur herstellung von (2s,3r,4s)-4-hydroxyisoleucin und analoga
AT390619B (de)	1990-06-11	Verfahren zur herstellung von neuen prolinderivaten
CH628900A5 (fr)	1982-03-31	Procede de preparation de thio-oximes derivees de cephalosporines et de penicillines.
DE3825242A1 (de)	1989-02-09	Durch schwefelhaltige gruppen substituierte histidinylamino-verbindungen
EP0271443B1 (fr)	1990-10-17	Urées N,N'-disubstituées et procédé pour leur préparation
EP0000500B1 (fr)	1982-04-28	Dérivés de, cephalosporine leur préparation et leurs compositions pharmaceutiques
EP0109362A1 (fr)	1984-05-23	Composés hétérocycliques, procédé pour leur préparation, compositions pharmaceutiques les contenant et leur application
DE69503905T2 (de)	1999-04-22	Peptidderivate mit metallopeptidasehemmender aktivität
EP0346281B1 (fr)	1992-06-17	Dérivés d'acide hydroxamique carbamoylé et procédé pour leur préparation
DE69614508T2 (de)	2002-04-11	Thiol derivate mit metallopeptidase inhibierender aktivitat
DE3431980A1 (de)	1985-04-18	Aminomethyl-verbindungen
DE69626846T2 (de)	2003-12-24	Phosphonsäurederivate mit metallopeptidase inhibierender aktivität
SI8810285A (sl)	1996-10-31	Postopek za pripravo derivatov 5-amino-4-hidroksi-valerianove kisline
DE3725137A1 (de)	1988-02-11	Neue peptide und peptidderivate, deren herstellung und sie enthaltende pharmazeutische zusammensetzungen
DE3222779A1 (de)	1983-01-27	Prolinderivate und verfahren zu deren herstellung
DD280764A5 (de)	1990-07-18	Verfahren zur herstellung von peptid-immunistimulantien