JPS60104099A - スパガリン関連化合物の新規製造法 - Google Patents

スパガリン関連化合物の新規製造法

Info

Publication number: JPS60104099A
Authority: JP; Japan
Prior art keywords: group; formula; triazadecane; aminoacyl; compound shown
Prior art date: 1983-11-09
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

JP58209099A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0253433B2 (de

Inventor

Masao Yoshida

雅男吉田

Tsugio Tomiyoshi

冨吉　次男

Masao Takei

竹井　征夫

Tetsuyuki Saino

哲之才野

Rinzo Nishizawa

西沢　林蔵

Teruya Nakamura

中村　輝也

Hamao Umezawa

梅沢　浜夫

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Takara Shuzo Co Ltd

Nippon Kayaku Co Ltd

Original Assignee

Takara Shuzo Co Ltd

Nippon Kayaku Co Ltd

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

1983-11-09

Filing date

1983-11-09

Publication date

1985-06-08

1983-11-09 Application filed by Takara Shuzo Co Ltd, Nippon Kayaku Co Ltd filed Critical Takara Shuzo Co Ltd

1983-11-09 Priority to JP58209099A priority Critical patent/JPS60104099A/ja

1985-06-08 Publication of JPS60104099A publication Critical patent/JPS60104099A/ja

1990-11-16 Publication of JPH0253433B2 publication Critical patent/JPH0253433B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title abstract description 22
GDVNLLJNADMLLR-BBRMVZONSA-N Spergualin Chemical compound NCCCNCCCCNC(=O)[C@H](O)NC(=O)C[C@@H](O)CCCCN=C(N)N GDVNLLJNADMLLR-BBRMVZONSA-N 0.000 title description 3
JBVZQDJNGFOSNX-UHFFFAOYSA-N Spergualin Natural products NCCCNCCCCNC(=O)C(O)NC(=O)CC(O)CCCCNC(=CN)N JBVZQDJNGFOSNX-UHFFFAOYSA-N 0.000 title description 3
125000006239 protecting group Chemical group 0.000 claims abstract description 21
125000003277 amino group Chemical group 0.000 claims abstract description 19
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims abstract description 16
239000004471 Glycine Substances 0.000 claims abstract description 8
MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims abstract description 7
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims abstract description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000003607 serino group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 4
239000002904 solvent Substances 0.000 abstract description 13
RMAHPRNLQIRHIJ-UHFFFAOYSA-N methyl carbamimidate Chemical compound COC(N)=N RMAHPRNLQIRHIJ-UHFFFAOYSA-N 0.000 abstract description 5
ATHGHQPFGPMSJY-UHFFFAOYSA-N spermidine Chemical compound NCCCCNCCCN ATHGHQPFGPMSJY-UHFFFAOYSA-N 0.000 abstract description 4
238000009835 boiling Methods 0.000 abstract description 3
239000002246 antineoplastic agent Substances 0.000 abstract 1
125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
-1 alkyl isoureas Chemical class 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
239000012153 distilled water Substances 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
239000010410 layer Substances 0.000 description 13
239000000047 product Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
239000007864 aqueous solution Substances 0.000 description 11
238000000034 method Methods 0.000 description 11
238000003786 synthesis reaction Methods 0.000 description 11
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
239000000203 mixture Substances 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
239000000126 substance Substances 0.000 description 6
GAZRNXIMWKZADY-UHFFFAOYSA-N 3,5-dimethylpyrazole-1-carboximidamide Chemical compound CC=1C=C(C)N(C(N)=N)N=1 GAZRNXIMWKZADY-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
238000001035 drying Methods 0.000 description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
238000003756 stirring Methods 0.000 description 5
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 5
QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000013078 crystal Substances 0.000 description 4
239000002274 desiccant Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
229960001153 serine Drugs 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
229920005654 Sephadex Polymers 0.000 description 3
239000012507 Sephadex™ Substances 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
238000005406 washing Methods 0.000 description 3
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000000266 alpha-aminoacyl group Chemical group 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
125000000539 amino acid group Chemical group 0.000 description 2
238000006664 bond formation reaction Methods 0.000 description 2
239000012267 brine Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000010531 catalytic reduction reaction Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
238000010828 elution Methods 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000011734 sodium Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
DZIUYPHPZLFPIH-UHFFFAOYSA-N 4-(1,3-diazinan-1-yl)butan-1-amine Chemical compound NCCCCN1CCCNC1 DZIUYPHPZLFPIH-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241001585244 Itame Species 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
KQJQICVXLJTWQD-UHFFFAOYSA-N N-Methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
241000534944 Thia Species 0.000 description 1
PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000004448 alkyl carbonyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
150000001540 azides Chemical class 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
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
238000001514 detection method Methods 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
150000002373 hemiacetals Chemical group 0.000 description 1
125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
244000005700 microbiome Species 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
125000002072 seryl group Chemical group 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000013076 target substance Substances 0.000 description 1
239000002966 varnish Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- 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

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Peptides Or Proteins (AREA)

JP58209099A 1983-11-09 1983-11-09 スパガリン関連化合物の新規製造法 Granted JPS60104099A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP58209099A JPS60104099A (ja)	1983-11-09	1983-11-09	スパガリン関連化合物の新規製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP58209099A JPS60104099A (ja)	1983-11-09	1983-11-09	スパガリン関連化合物の新規製造法

Publications (2)

Publication Number	Publication Date
JPS60104099A true JPS60104099A (ja)	1985-06-08
JPH0253433B2 JPH0253433B2 (de)	1990-11-16

Family

ID=16567270

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP58209099A Granted JPS60104099A (ja)	1983-11-09	1983-11-09	スパガリン関連化合物の新規製造法

Country Status (1)

Country	Link
JP (1)	JPS60104099A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4956504A (en) *	1986-04-04	1990-09-11	Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai	Novel spergualin-related compounds and process for producing the same

1983
- 1983-11-09 JP JP58209099A patent/JPS60104099A/ja active Granted

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4956504A (en) *	1986-04-04	1990-09-11	Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai	Novel spergualin-related compounds and process for producing the same

Also Published As

Publication number	Publication date
JPH0253433B2 (de)	1990-11-16

Publication	Publication Date	Title
JPS5942356A (ja)	1984-03-08	スパガリン関連化合物およびその製造法
PT95629A (pt)	1991-09-13	Processo para a preparacao de compostos de adenosina n-(6)substituida
EP0460446B1 (de)	1993-04-07	Ein neues Kupplungsreagenz für die Peptidsynthese
JPS60104099A (ja)	1985-06-08	スパガリン関連化合物の新規製造法
SE447259B (sv)	1986-11-03	Forfarande for framstellning av ett 1-n-/l-(-)-omega-amino-alfa-hydroxialkanoyl/kanamycin a eller b
AU738462B2 (en)	2001-09-20	Process for the synthesis of chloropurine intermediates
GB2087876A (en)	1982-06-03	Novel nitrosourea derivatives
JPS60231694A (ja)	1985-11-18	アスパルチルペプチドの調整に関する組成物および方法
KR100708581B1 (ko)	2007-04-18	리토나비르의 합성 방법
JPS61263995A (ja)	1986-11-21	シトシンヌクレオシド類の製造法
AU2008333153A1 (en)	2009-06-11	Process for the preparation of 2-(primary/secondary amino)hydrocarbyl)- carbamoyl-7-oxo-2,6-diaza-bicyclo[3.2.0.]heptane-6-sulfonic acid derivatives
JPH02160772A (ja)	1990-06-20	新規なチオプロリン誘導体
EP0309971A2 (de)	1989-04-05	Pergualinähnliche Verbindungen und pharmazeutisches Mittel
JPS636080B2 (de)	1988-02-08
JPS58172399A (ja)	1983-10-11	ムラミルトリペプチド誘導体
US5079375A (en)	1992-01-07	Process for the synthesis of N.sup.α -fluorenylmethoxycarbonyl-NG -trityl-arginine
JPS61129159A (ja)	1986-06-17	保護化アミノ酸アミド化合物の精製法
JPS591268B2 (ja)	1984-01-11	チアジアゾ−ル誘導体
JPH02131458A (ja)	1990-05-21	新スパガリン関連化合物、その製造法及びその用途
JP3134010B2 (ja)	2001-02-13	デスアラニンベナノマイシンａ誘導体およびそれらの製造法
RU1781226C (ru)	1992-12-15	Способ получени пироглутамилсодержащих субстратов
JPS5946250A (ja)	1984-03-15	エピニンエステル類
JPS61260052A (ja)	1986-11-18	新規アミノ酸誘導体および甘味剤
JPS6328075B2 (de)	1988-06-07
JPH029859A (ja)	1990-01-12	スルホニウム化合物の製造方法

JPS60104099A - スパガリン関連化合物の新規製造法 - Google Patents

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