NO131543B - - Google Patents

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Info

Publication number: NO131543B
Authority: NO; Norway
Prior art keywords: lys; boc; gly; boe; mmol
Prior art date: 1969-10-31

Application number

NO4143/70A

Other languages

English (en)

Norwegian (no)

Other versions

NO131543C (fr

Inventor

R Geiger

H-G Schroeder

Original Assignee

Hoechst 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.)

1969-10-31

Filing date

1970-10-30

Publication date

1975-03-10

1970-10-30 Application filed by Hoechst Ag filed Critical Hoechst Ag

1975-03-10 Publication of NO131543B publication Critical patent/NO131543B/no

1975-06-18 Publication of NO131543C publication Critical patent/NO131543C/no

Links

108090000765 processed proteins & peptides Proteins 0.000 claims description 21
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 17
102000004196 processed proteins & peptides Human genes 0.000 claims description 13
-1 Boc-D-seryl Chemical group 0.000 claims description 9
125000006239 protecting group Chemical group 0.000 claims description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 3
239000004472 Lysine Substances 0.000 claims description 3
AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 3
UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims description 3
229960003104 ornithine Drugs 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000000722 D-seryl group Chemical group N[C@@H](C(=O)*)CO 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
150000001875 compounds Chemical class 0.000 description 23
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
229940024606 amino acid Drugs 0.000 description 10
150000001413 amino acids Chemical class 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
238000000746 purification Methods 0.000 description 9
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 7
150000001408 amides Chemical class 0.000 description 7
238000004458 analytical method Methods 0.000 description 7
230000000694 effects Effects 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 6
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
229920002134 Carboxymethyl cellulose Polymers 0.000 description 5
102400000739 Corticotropin Human genes 0.000 description 5
101800000414 Corticotropin Proteins 0.000 description 5
239000000055 Corticotropin-Releasing Hormone Substances 0.000 description 5
239000001768 carboxy methyl cellulose Substances 0.000 description 5
235000010948 carboxy methyl cellulose Nutrition 0.000 description 5
239000008112 carboxymethyl-cellulose Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 5
229960000258 corticotropin Drugs 0.000 description 5
IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 5
238000003756 stirring Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 4
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
230000004071 biological effect Effects 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 description 2
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 2
VZXOZSQDJJNBRC-UHFFFAOYSA-N 4-chlorobenzenethiol Chemical compound SC1=CC=C(Cl)C=C1 VZXOZSQDJJNBRC-UHFFFAOYSA-N 0.000 description 2
HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 2
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 2
AXBVSRMHOPMXBA-UHFFFAOYSA-N 4-nitrothiophenol Chemical compound [O-][N+](=O)C1=CC=C(S)C=C1 AXBVSRMHOPMXBA-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
230000003023 adrenocorticotropic effect Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
229940081974 saccharin Drugs 0.000 description 2
235000019204 saccharin Nutrition 0.000 description 2
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 2
229960001153 serine Drugs 0.000 description 2
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
HJBLUNHMOKFZQX-UHFFFAOYSA-N 3-hydroxy-1,2,3-benzotriazin-4-one Chemical class C1=CC=C2C(=O)N(O)N=NC2=C1 HJBLUNHMOKFZQX-UHFFFAOYSA-N 0.000 description 1
ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
101100505076 Caenorhabditis elegans gly-2 gene Proteins 0.000 description 1
102000005367 Carboxypeptidases Human genes 0.000 description 1
108010006303 Carboxypeptidases Proteins 0.000 description 1
MTCFGRXMJLQNBG-UWTATZPHSA-N D-Serine Chemical compound OC[C@@H](N)C(O)=O MTCFGRXMJLQNBG-UWTATZPHSA-N 0.000 description 1
229930195711 D-Serine Natural products 0.000 description 1
QNAYBMKLOCPYGJ-UWTATZPHSA-N D-alanine Chemical compound C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 1
QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
AYFVYJQAPQTCCC-STHAYSLISA-N D-threonine Chemical compound C[C@H](O)[C@@H](N)C(O)=O AYFVYJQAPQTCCC-STHAYSLISA-N 0.000 description 1
229930182822 D-threonine Natural products 0.000 description 1
125000002842 L-seryl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])O[H] 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
102000007079 Peptide Fragments Human genes 0.000 description 1
108010033276 Peptide Fragments Proteins 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
UYKREHOKELZSPB-JTQLQIEISA-N Trp-Gly Chemical compound C1=CC=C2C(C[C@H](N)C(=O)NCC(O)=O)=CNC2=C1 UYKREHOKELZSPB-JTQLQIEISA-N 0.000 description 1
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
229940124277 aminobutyric acid Drugs 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
235000014121 butter Nutrition 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000005187 foaming Methods 0.000 description 1
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
YMAWOPBAYDPSLA-UHFFFAOYSA-N glycylglycine Chemical compound [NH3+]CC(=O)NCC([O-])=O YMAWOPBAYDPSLA-UHFFFAOYSA-N 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
239000005556 hormone Substances 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000203 mixture 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
NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical class OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
238000013094 purity test Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000004904 shortening Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000001228 spectrum 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
238000012360 testing method Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/665—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans derived from pro-opiomelanocortin, pro-enkephalin or pro-dynorphin
- C07K14/695—Corticotropin [ACTH]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- 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)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Gastroenterology & Hepatology (AREA)
Biochemistry (AREA)
Biophysics (AREA)
Zoology (AREA)
Genetics & Genomics (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Toxicology (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)

NO4143/70A 1969-10-31 1970-10-30 NO131543C (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE1954794A DE1954794C3 (de)	1969-10-31	1969-10-31	Peptide mit adrenocorticotroper Wirkung und Verfahren zu ihrer Her stellung

Publications (2)

Publication Number	Publication Date
NO131543B true NO131543B (fr)	1975-03-10
NO131543C NO131543C (fr)	1975-06-18

Family

ID=5749760

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO4143/70A NO131543C (fr)	1969-10-31	1970-10-30

Country Status (12)

Country	Link
US (1)	US3749704A (fr)
JP (1)	JPS4826011B1 (fr)
AT (1)	AT298700B (fr)
BE (1)	BE758206A (fr)
CA (1)	CA923495A (fr)
CH (1)	CH550144A (fr)
DE (1)	DE1954794C3 (fr)
FR (1)	FR2070182B1 (fr)
GB (1)	GB1329618A (fr)
NL (1)	NL7015658A (fr)
NO (1)	NO131543C (fr)
SE (1)	SE361878B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5116667A (fr) *	1974-07-30	1976-02-10	Shionogi Seiyaku Kk
US4089821A (en) *	1976-03-31	1978-05-16	Armour Pharmaceutical Company	Synthesis of peptide amides
IT1204434B (it) *	1986-01-15	1989-03-01	Alfio Bertolini	Composizioni farmaceutiche comprendenti frammenti di acth per il trattamento terapeutico degli stati di shock e dell'insufficienza respiratoria e cardiocircolatoria
DE3931788A1 (de) *	1989-09-23	1991-04-04	Hoechst Ag	Neue zns-aktive hexapeptide mit antiamnestischer wirkung
DE102018207815A1 (de)	2018-05-18	2019-11-21	Karl Wörwag Lack- Und Farbenfabrik Gmbh & Co. Kg	Mehrschichtige, farb- und/oder effektgebende Lackierung sowie Verfahren zur Bildung einer Basislackschicht

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE668250A (fr) *	1964-08-13
CH490338A (de) *	1967-04-13	1970-05-15	Ciba Geigy	Verfahren zur Herstellung von ACTH-wirksamen Peptiden mit verlängerter Wirkung
BE724772A (fr) *	1967-12-01	1969-06-02

0
- BE BE758206D patent/BE758206A/fr not_active IP Right Cessation
1969
- 1969-10-31 DE DE1954794A patent/DE1954794C3/de not_active Expired
1970
- 1970-10-26 FR FR7038524A patent/FR2070182B1/fr not_active Expired
- 1970-10-26 NL NL7015658A patent/NL7015658A/xx not_active Application Discontinuation
- 1970-10-29 AT AT09749/70A patent/AT298700B/de not_active IP Right Cessation
- 1970-10-29 US US00085216A patent/US3749704A/en not_active Expired - Lifetime
- 1970-10-29 GB GB5146270A patent/GB1329618A/en not_active Expired
- 1970-10-29 CH CH1614870A patent/CH550144A/xx not_active IP Right Cessation
- 1970-10-30 CA CA097073A patent/CA923495A/en not_active Expired
- 1970-10-30 SE SE14665/70A patent/SE361878B/xx unknown
- 1970-10-30 NO NO4143/70A patent/NO131543C/no unknown
- 1970-10-31 JP JP45096359A patent/JPS4826011B1/ja active Pending

Also Published As

Publication number	Publication date
SE361878B (fr)	1973-11-19
NO131543C (fr)	1975-06-18
NL7015658A (fr)	1971-05-04
AT298700B (de)	1972-04-15
FR2070182A1 (fr)	1971-09-10
GB1329618A (en)	1973-09-12
CA923495A (en)	1973-03-27
US3749704A (en)	1973-07-31
DE1954794B2 (de)	1973-05-24
DE1954794C3 (de)	1973-12-13
BE758206A (fr)	1971-04-29
JPS4826011B1 (fr)	1973-08-03
DE1954794A1 (de)	1971-05-06
CH550144A (de)	1974-06-14
FR2070182B1 (fr)	1974-04-12

Publication	Publication Date	Title
US3929758A (en)	1975-12-30	Cyclization of cysteine-containing peptides
EP0285562B1 (fr)	1993-04-28	Résine synthétique
AU636301B2 (en)	1993-04-29	Cyclic grf-analogs ii
JP2542362B2 (ja)	1996-10-09	新規ハロ低級アルキルグアニジノ置換アミノ酸化合物およびその製法
DE3144818A1 (de)	1982-08-19	C-terminales fragment von menschlichem choriongonadotropin
DK167361B1 (da)	1993-10-18	Grf-analoge peptider, farmaceutisk acceptable salte heraf og fremgangsmaader til fremstilling af disse
US3883500A (en)	1975-05-13	Process for the manufacture of insulin, analogs and derivatives thereof
US3883496A (en)	1975-05-13	Process for the manufacture of insulin, analogs and derivatives thereof
EP0226217A2 (fr)	1987-06-24	Peptides ayant des groupes ester-sulfate
NO131543B (fr)	1975-03-10
CA1253299A (fr)	1989-04-25	Polypeptide et procede de production
US3862927A (en)	1975-01-28	Process for preparation of vasoactive intestinal peptide
EP0268297A2 (fr)	1988-05-25	Peptides avec groupes ester sulfate
CA1059993A (fr)	1979-08-07	Polypeptides
CZ282881B6 (cs)	1997-11-12	Způsob výroby peptidů
US4152322A (en)	1979-05-01	Process for selective reduction of nitroarginyl peptides with titanium (iii)
GB1590668A (en)	1981-06-03	Process for the preparation of thymosin a1 and an analogue
US4474765A (en)	1984-10-02	Biologically active peptides
US4105652A (en)	1978-08-08	Synthesis of human β-endorphin
Mergler et al.	1999	SASRIN™, a Versatile Tool in Peptide Synthesis and Solid-Phase Organic Chemistry
JPS6136298A (ja)	1986-02-20	トリペプチドアミド類
AP546A (en)	1996-10-29	Peptides for inhibiting pepsin release.
US3738978A (en)	1973-06-12	Process for the manufacture of peptides
Suli-Vargha et al.	1987	Synthesis and antitumor activity of N-terminal proline-containing peptide-(chloroethyl) nitrosoureas
DE1965102A1 (de)	1971-07-01	Neue Tridekapeptide mit hoher adrenocorticotroper Wirkung und Verfahren zu ihrer Herstellung