CH619468A5 - - Google Patents

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Info

Publication number: CH619468A5
Authority: CH; Switzerland
Prior art keywords: methylene chloride; formula; acid; compounds; solution
Prior art date: 1976-01-12

Application number

CH26976A

Other languages

German (de)

English (en)

Inventor

Paul Dr Stadler

Original Assignee

Sandoz Ag

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.)

1976-01-12

Filing date

1976-01-12

Publication date

1980-09-30

1976-01-12 Application filed by Sandoz Ag filed Critical Sandoz Ag

1976-01-12 Priority to CH26976A priority Critical patent/CH619468A5/de

1977-01-03 Priority to DK000577A priority patent/DK150490C/da

1977-01-03 Priority to FI770008A priority patent/FI62094C/fi

1977-01-05 Priority to SE7700084A priority patent/SE434401B/xx

1977-01-05 Priority to DE19772700234 priority patent/DE2700234A1/de

1977-01-07 Priority to NL7700124A priority patent/NL7700124A/xx

1977-01-07 Priority to US05/757,616 priority patent/US4145549A/en

1977-01-10 Priority to ES454917A priority patent/ES454917A1/es

1977-01-10 Priority to IE43/77A priority patent/IE44560B1/en

1977-01-10 Priority to CA269,389A priority patent/CA1108128A/en

1977-01-10 Priority to NZ183045A priority patent/NZ183045A/xx

1977-01-10 Priority to HU77SA3003A priority patent/HU176871B/hu

1977-01-11 Priority to AU21228/77A priority patent/AU512003B2/en

1977-01-11 Priority to GB916/77A priority patent/GB1571835A/en

1977-01-11 Priority to AT0008777A priority patent/AT364817B/de

1977-01-11 Priority to JP123977A priority patent/JPS5287197A/ja

1977-01-11 Priority to CS77170A priority patent/CS200205B2/cs

1977-01-12 Priority to BE174010A priority patent/BE850304A/xx

1977-01-12 Priority to SU772439829A priority patent/SU725565A3/ru

1977-01-12 Priority to YU62/77A priority patent/YU39377B/xx

1977-01-12 Priority to FR7700760A priority patent/FR2337727A1/fr

1977-01-12 Priority to ZA00770151A priority patent/ZA77151B/xx

1980-09-30 Publication of CH619468A5 publication Critical patent/CH619468A5/de

Links

-1 phenyloxy Chemical group 0.000 claims description 28
238000000034 method Methods 0.000 claims description 12
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 6
238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 126
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
150000001875 compounds Chemical class 0.000 description 46
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
239000002253 acid Substances 0.000 description 23
239000000203 mixture Substances 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
125000000217 alkyl group Chemical group 0.000 description 13
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 12
150000002148 esters Chemical class 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000000126 substance Substances 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
125000006239 protecting group Chemical group 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 7
239000001257 hydrogen Substances 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
239000000725 suspension Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
108090000765 processed proteins & peptides Proteins 0.000 description 5
239000000047 product Substances 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
230000032050 esterification Effects 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
239000006260 foam Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
239000011736 potassium bicarbonate Substances 0.000 description 4
229910000028 potassium bicarbonate Inorganic materials 0.000 description 4
235000015497 potassium bicarbonate Nutrition 0.000 description 4
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
238000003756 stirring Methods 0.000 description 4
OTLNPYWUJOZPPA-UHFFFAOYSA-M 4-nitrobenzoate Chemical compound [O-]C(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-M 0.000 description 3
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
239000000284 extract Substances 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
235000002906 tartaric acid Nutrition 0.000 description 3
239000011975 tartaric acid Substances 0.000 description 3
XJJBXZIKXFOMLP-ZETCQYMHSA-N tert-butyl (2s)-pyrrolidine-2-carboxylate Chemical compound CC(C)(C)OC(=O)[C@@H]1CCCN1 XJJBXZIKXFOMLP-ZETCQYMHSA-N 0.000 description 3
JXGVXCZADZNAMJ-NSHDSACASA-N (2s)-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1C(=O)OCC1=CC=CC=C1 JXGVXCZADZNAMJ-NSHDSACASA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
WEQJQNWXCSUVMA-RYUDHWBXSA-N Phe-Pro Chemical compound C([C@H]([NH3+])C(=O)N1[C@@H](CCC1)C([O-])=O)C1=CC=CC=C1 WEQJQNWXCSUVMA-RYUDHWBXSA-N 0.000 description 2
RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
229940024606 amino acid Drugs 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
229960003133 ergot alkaloid Drugs 0.000 description 2
150000002431 hydrogen Chemical group 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
FSIZNIXUPRQTLZ-QMTHXVAHSA-N lysergic acid Chemical compound C1=CC=C2C3=C[C@@H](C(O)=O)CN(C)[C@@H]3CC3=CN=C1[C]32 FSIZNIXUPRQTLZ-QMTHXVAHSA-N 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
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 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
WKVZMKDXJFCMMD-UVWUDEKDSA-L (5ar,8ar,9r)-5-[[(2r,4ar,6r,7r,8r,8as)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one;azanide;n,3-bis(2-chloroethyl)-2-ox Chemical compound [NH2-].[NH2-].Cl[Pt+2]Cl.ClCCNP1(=O)OCCCN1CCCl.COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3C(O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 WKVZMKDXJFCMMD-UVWUDEKDSA-L 0.000 description 1
ORBSYPFBZQJNJE-MPKXVKKWSA-N (6ar,9r,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carboxylic acid Chemical compound C1=CC([C@H]2C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ORBSYPFBZQJNJE-MPKXVKKWSA-N 0.000 description 1
OULMZZGGALAOLR-AWEZNQCLSA-N 1-o-benzyl 2-o-tert-butyl (2s)-pyrrolidine-1,2-dicarboxylate Chemical compound CC(C)(C)OC(=O)[C@@H]1CCCN1C(=O)OCC1=CC=CC=C1 OULMZZGGALAOLR-AWEZNQCLSA-N 0.000 description 1
125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 1
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
ZAGRKAFMISFKIO-UHFFFAOYSA-N Isolysergic acid Natural products C1=CC(C2=CC(CN(C2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-UHFFFAOYSA-N 0.000 description 1
229930182821 L-proline Natural products 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
OMOVVBIIQSXZSZ-UHFFFAOYSA-N [6-(4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3h-pyrano[3,4-b]oxepin-5-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-hydroxy-3-methylpentanoate Chemical compound CC12C(OC(=O)C(O)C(C)CC)C(OC=O)C(C3(C)C(CC(=O)OC4(C)COC(=O)CC43)OC(C)=O)C(=C)C32OC3CC1C=1C=COC=1 OMOVVBIIQSXZSZ-UHFFFAOYSA-N 0.000 description 1
SGKGCCPPTVUYOO-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C=CC=C1)O.C(C)#N Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)O.C(C)#N SGKGCCPPTVUYOO-UHFFFAOYSA-N 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
210000003608 fece Anatomy 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
239000012071 phase Substances 0.000 description 1
229960005190 phenylalanine Drugs 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
229960004109 potassium acetate Drugs 0.000 description 1
KYKNRZGSIGMXFH-ZVGUSBNCSA-M potassium bitartrate Chemical compound [K+].OC(=O)[C@H](O)[C@@H](O)C([O-])=O KYKNRZGSIGMXFH-ZVGUSBNCSA-M 0.000 description 1
239000001508 potassium citrate Substances 0.000 description 1
229960002635 potassium citrate Drugs 0.000 description 1
QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
235000011082 potassium citrates Nutrition 0.000 description 1
239000001472 potassium tartrate Substances 0.000 description 1
229940111695 potassium tartrate Drugs 0.000 description 1
235000011005 potassium tartrates Nutrition 0.000 description 1
229960002429 proline Drugs 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000001433 sodium tartrate Substances 0.000 description 1
229960002167 sodium tartrate Drugs 0.000 description 1
235000011004 sodium tartrates Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/081—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing O or S as heteroatoms, e.g. Cys, Ser
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Genetics & Genomics (AREA)
Biochemistry (AREA)
Biophysics (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Life Sciences & Earth Sciences (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

CH26976A 1976-01-12 1976-01-12 CH619468A5 (da)

Priority Applications (22)

Application Number	Priority Date	Filing Date	Title
CH26976A CH619468A5 (da)	1976-01-12	1976-01-12
DK000577A DK150490C (da)	1976-01-12	1977-01-03	Fremgangsmaade til fremstilling af 2-aminooctahydro-oxazolo-(3,2-a)pyrrolo(2,1-c)pyrazinderivater
FI770008A FI62094C (fi)	1976-01-12	1977-01-03	Foerfarande foer framstaellning av 2-amino-oktahydro-oxazolo(3,2-a)pyrrolo(2,1-c)pyratzinderivat
SE7700084A SE434401B (sv)	1976-01-12	1977-01-05	Forfarande for framstellning av 2-karbobensoxiamino-oktahydro-oxazolo(3,2-a)pyrrolo(2,1-c)pyrazinderivat
DE19772700234 DE2700234A1 (de)	1976-01-12	1977-01-05	Organische verbindungen und verfahren zu deren herstellung
NL7700124A NL7700124A (nl)	1976-01-12	1977-01-07	Werkwijzen voor het bereiden en toepassen van heterocyclische verbindingen.
US05/757,616 US4145549A (en)	1976-01-12	1977-01-07	Process for preparing oxazolo 3,2-a!pyrrolo 2,1-c!pyrazine derivatives
ES454917A ES454917A1 (es)	1976-01-12	1977-01-10	Procedimiento para la produccion de aminocicloles.
IE43/77A IE44560B1 (en)	1976-01-12	1977-01-10	Aminicyclols
CA269,389A CA1108128A (en)	1976-01-12	1977-01-10	Cyclization process for an ergot alkaloid
NZ183045A NZ183045A (en)	1976-01-12	1977-01-10	Aminocylol production
HU77SA3003A HU176871B (en)	1976-01-12	1977-01-10	Process for producing 2-amino-oktahydro-oxasolo-square bracket-3,2-a-square bracket closed-pyrrolo-square bracket-2,1-c-square bracket closed-pyrasine derivatives
AU21228/77A AU512003B2 (en)	1976-01-12	1977-01-11	Oxazolo(3, 2-a) pyrolo-2-(2, 1-c) pyrazine derivatives
GB916/77A GB1571835A (en)	1976-01-12	1977-01-11	Aminocyclols
AT0008777A AT364817B (de)	1976-01-12	1977-01-11	Verfahren zur herstellung von aminocyclolen
JP123977A JPS5287197A (en)	1976-01-12	1977-01-11	Improvement in organic compound
CS77170A CS200205B2 (en)	1976-01-12	1977-01-11	Method of producing aminocyclols
BE174010A BE850304A (fr)	1976-01-12	1977-01-12	Procede de preparation de composes peptidiques
SU772439829A SU725565A3 (ru)	1976-01-12	1977-01-12	Способ получени производных октагидрооксазоло/3,2-а/пирроло /2,1-с/пиразина
YU62/77A YU39377B (en)	1976-01-12	1977-01-12	Process for the manufacture of aminocyclols
FR7700760A FR2337727A1 (fr)	1976-01-12	1977-01-12	Procede de preparation de composes peptidiques
ZA00770151A ZA77151B (en)	1976-01-12	1977-01-12	Improvements in or relating to organic compounds

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH26976A CH619468A5 (da)	1976-01-12	1976-01-12

Publications (1)

Publication Number	Publication Date
CH619468A5 true CH619468A5 (da)	1980-09-30

Family

ID=4183149

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH26976A CH619468A5 (da)	1976-01-12	1976-01-12

Country Status (22)

Country	Link
US (1)	US4145549A (da)
JP (1)	JPS5287197A (da)
AT (1)	AT364817B (da)
AU (1)	AU512003B2 (da)
BE (1)	BE850304A (da)
CA (1)	CA1108128A (da)
CH (1)	CH619468A5 (da)
CS (1)	CS200205B2 (da)
DE (1)	DE2700234A1 (da)
DK (1)	DK150490C (da)
ES (1)	ES454917A1 (da)
FI (1)	FI62094C (da)
FR (1)	FR2337727A1 (da)
GB (1)	GB1571835A (da)
HU (1)	HU176871B (da)
IE (1)	IE44560B1 (da)
NL (1)	NL7700124A (da)
NZ (1)	NZ183045A (da)
SE (1)	SE434401B (da)
SU (1)	SU725565A3 (da)
YU (1)	YU39377B (da)
ZA (1)	ZA77151B (da)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1584464A (en) *	1977-04-19	1981-02-11	Farmaceutici Italia	Ergot alkaloids
JPS5423487U (da) *	1977-07-19	1979-02-15
DE2962303D1 (en) *	1978-01-20	1982-04-29	Sandoz Ag	Derivatives of ergopeptide alkaloids, process for their preparation and pharmaceutical compositions containing them
YU41110B (en) *	1978-07-19	1986-12-31	Lek Tovarna Farmacevtskih	Process for preparing dextrorotatory ergot alcaloids acid addition salts
DE3303616A1 (de) *	1982-02-12	1983-08-25	Sandoz-Patent-GmbH, 7850 Lörrach	Mutterkornalkaloide, verfahren zu deren herstellung sowie diese verbindungen enthaltende pharmazeutische zubereitungen
RU2266906C1 (ru) *	2004-04-29	2005-12-27	Общество с ограниченной ответственностью "Исследовательский Институт Химического Разнообразия" (ООО "Исследовательский Институт Химического Разнообразия")	Анелированные карбамоилазагетероциклы, способы их получения (варианты), фармацевтическая композиция, фокусированная библиотека
US20080161324A1 (en) *	2006-09-14	2008-07-03	Johansen Lisa M	Compositions and methods for treatment of viral diseases

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2533698A (en) *		1950-12-12		Urethanes containing the lysergic
CH507249A (de) *	1968-05-31	1971-05-15	Sandoz Ag	Verfahren zur Herstellung von 2-Brom-a-ergokryptin
GB1298277A (en) *	1969-04-18	1972-11-29	Sandoz Ltd	Preparation of ergot peptide alkaloids
JPS4735440A (da) *	1971-03-29	1972-11-25
CH581136A5 (da) *	1972-09-26	1976-10-29	Sandoz Ag
SE397093B (sv) *	1973-07-09	1977-10-17	Sandoz Ag	Forfarande for framstellning av oktahydro-oxazolo(3,2-a)pyrrolo(2,1-c)pyrazinderivat
CH587858A5 (da) *	1973-11-28	1977-05-13	Sandoz Ag
DE2525962A1 (de) *	1974-06-21	1976-01-08	Sandoz Ag	Neue heterocyclische verbindungen, ihre herstellung und verwendung
CH601321A5 (da) *	1975-01-06	1978-07-14	Sandoz Ag

1976
- 1976-01-12 CH CH26976A patent/CH619468A5/de not_active IP Right Cessation
1977
- 1977-01-03 FI FI770008A patent/FI62094C/fi not_active IP Right Cessation
- 1977-01-03 DK DK000577A patent/DK150490C/da not_active Application Discontinuation
- 1977-01-05 DE DE19772700234 patent/DE2700234A1/de not_active Withdrawn
- 1977-01-05 SE SE7700084A patent/SE434401B/xx not_active IP Right Cessation
- 1977-01-07 NL NL7700124A patent/NL7700124A/xx not_active Application Discontinuation
- 1977-01-07 US US05/757,616 patent/US4145549A/en not_active Expired - Lifetime
- 1977-01-10 HU HU77SA3003A patent/HU176871B/hu unknown
- 1977-01-10 ES ES454917A patent/ES454917A1/es not_active Expired
- 1977-01-10 IE IE43/77A patent/IE44560B1/en unknown
- 1977-01-10 NZ NZ183045A patent/NZ183045A/xx unknown
- 1977-01-10 CA CA269,389A patent/CA1108128A/en not_active Expired
- 1977-01-11 AU AU21228/77A patent/AU512003B2/en not_active Expired
- 1977-01-11 CS CS77170A patent/CS200205B2/cs unknown
- 1977-01-11 AT AT0008777A patent/AT364817B/de not_active IP Right Cessation
- 1977-01-11 GB GB916/77A patent/GB1571835A/en not_active Expired
- 1977-01-11 JP JP123977A patent/JPS5287197A/ja active Pending
- 1977-01-12 YU YU62/77A patent/YU39377B/xx unknown
- 1977-01-12 BE BE174010A patent/BE850304A/xx not_active IP Right Cessation
- 1977-01-12 SU SU772439829A patent/SU725565A3/ru active
- 1977-01-12 FR FR7700760A patent/FR2337727A1/fr active Granted
- 1977-01-12 ZA ZA00770151A patent/ZA77151B/xx unknown

Also Published As

Publication number	Publication date
CS200205B2 (en)	1980-08-29
IE44560B1 (en)	1982-01-13
SE434401B (sv)	1984-07-23
DK577A (da)	1977-07-13
BE850304A (fr)	1977-07-12
DK150490C (da)	1987-10-19
DE2700234A1 (de)	1977-07-14
JPS5287197A (en)	1977-07-20
US4145549A (en)	1979-03-20
FI770008A (da)	1977-07-13
FI62094B (fi)	1982-07-30
FI62094C (fi)	1982-11-10
CA1108128A (en)	1981-09-01
IE44560L (en)	1977-07-12
FR2337727B1 (da)	1980-04-30
HU176871B (en)	1981-05-28
AU2122877A (en)	1978-07-20
SU725565A3 (ru)	1980-03-30
ES454917A1 (es)	1978-04-01
AT364817B (de)	1981-11-25
ZA77151B (en)	1978-08-30
NZ183045A (en)	1979-03-16
YU6277A (en)	1982-10-31
ATA8777A (de)	1981-04-15
FR2337727A1 (fr)	1977-08-05
NL7700124A (nl)	1977-07-14
AU512003B2 (en)	1980-09-18
GB1571835A (en)	1980-07-23
DK150490B (da)	1987-03-09
YU39377B (en)	1984-12-31

Publication	Publication Date	Title
DE2759862C2 (da)	1989-12-07
EP0089637B1 (de)	1986-10-15	Neue Derivate bicyclischer Aminosäuren, Verfahren zu ihrer Herstellung, diese enthaltende Mittel und deren Verwendung sowie neue bicyclische Aminosäuren als Zwischenstufen und Verfahren zu deren Herstellung
CH633544A5 (de)	1982-12-15	Verfahren zur herstellung von thiazolessigsaeureverbindungen.
DD201782A5 (de)	1983-08-10	Verfahren zur herstellung von octahydro-1-(omega-mercaptoalkanoyl)-1h-indol 2-carbonsaeure-verbindungen
DE68920632T2 (de)	1995-06-14	Antiamnesische Pyrrolidin-Derivate.
EP0115639B1 (de)	1987-03-04	Disubstituierte Prolinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung
DE60209458T2 (de)	2006-10-12	Verfahren zur Synthese von (2S,3aS,7aS)-1-(S)-Alanyl-octahydro-1H-2-carbonsäurederivaten und Verwendung in der Synthese von Perindopril
DE2934592C2 (da)	1989-10-05
EP0270982A2 (de)	1988-06-15	Derivate bicyclischer Aminocarbonsäuren, Verfahren und Zwischenprodukte zu deren Herstellung sowie deren Verwendung
CH631987A5 (de)	1982-09-15	Verfahren zur herstellung von 7-acylamino-8-oxo-3-oxa-1-azabicyclo(4.2.0)octan-2-carbonsaeure-derivaten.
CH619468A5 (da)	1980-09-30
DE3434121C2 (da)	1992-11-19
CH627475A5 (en)	1982-01-15	Process for preparing cephem compounds as intermediates for the synthesis of cephalosporins
DE69839056T2 (de)	2009-01-15	Stereoisomere indolderivate, verfahren zu ihrer herstellung und ihre verwendung
CH653996A5 (de)	1986-01-31	Tryptaminderivate und verfahren zu deren herstellung.
CH642658A5 (de)	1984-04-30	Racemische bzw. optisch aktive oximino-e-homo-eburnan-derivate sowie verfahren zu deren herstellung.
AT395148B (de)	1992-09-25	Verfahren zur herstellung von 1-(3-mercapto-(2s)methyl-1-oxo-propyl)-l-prolin
DE2944086A1 (de)	1980-05-14	Peptidderivate
DE3526023C2 (da)	1988-10-20
CH633290A5 (en)	1982-11-30	Process for preparing derivatives of 7-oxo-1,3-diazabicyclo[3.2.0]heptane-2-carboxylic acid
DE2800064A1 (de)	1979-07-12	Verfahren zur herstellung von 2-amino-3,6-dioxo-octahydro-8h-oxazolo eckige klammer auf 3,2-a eckige klammer zu pyrrolo eckige klammer auf 2,1-c eckige klammer zu pyrazin-derivaten
EP0154886A2 (de)	1985-09-18	Carboxyalkyldipeptidderivate, Verfahren zu deren Herstellung, diese enthaltende Mittel und deren Verwendung
CH655928A5 (de)	1986-05-30	Neue heterocyclische essigsaeuren und verfahren zu ihrer herstellung.
AT384215B (de)	1987-10-12	Verfahren zur herstellung von neuen, heterocyclischen essigsaeuren
DE2707404A1 (de)	1977-08-25	5,6-dehydropenicilline und verfahren zu deren herstellung und mittel zur durchfuehrung des verfahrens

Legal Events

Date	Code	Title	Description
1987-09-30	PL	Patent ceased
2024-10-31	PL	Patent ceased