JPH0254822B2 - - Google Patents
Info
- Publication number
- JPH0254822B2 JPH0254822B2 JP3429884A JP3429884A JPH0254822B2 JP H0254822 B2 JPH0254822 B2 JP H0254822B2 JP 3429884 A JP3429884 A JP 3429884A JP 3429884 A JP3429884 A JP 3429884A JP H0254822 B2 JPH0254822 B2 JP H0254822B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- guanidinoheptanoyl
- mmol
- formula
- reduced pressure
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 40
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 108091005804 Peptidases Proteins 0.000 claims description 4
- 102000035195 Peptidases Human genes 0.000 claims description 4
- 235000019833 protease Nutrition 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000010934 O-alkylation reaction Methods 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims 1
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims 1
- 235000008206 alpha-amino acids Nutrition 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 92
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- 239000000047 product Substances 0.000 description 29
- -1 Guanidino fatty acid Chemical class 0.000 description 26
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 24
- 239000000243 solution Substances 0.000 description 20
- 229920005654 Sephadex Polymers 0.000 description 19
- 239000012507 Sephadex™ Substances 0.000 description 19
- 239000011734 sodium Substances 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 14
- 239000011780 sodium chloride Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- XYZVTJQQUFLMJY-UHFFFAOYSA-N 2-amino-2-methoxyacetic acid Chemical compound COC(N)C(O)=O XYZVTJQQUFLMJY-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- VBJNGFKLXFJKQR-UHFFFAOYSA-N 2-[7-(diaminomethylideneamino)heptanoylamino]-2-phenylmethoxyacetic acid Chemical compound NC(=N)NCCCCCCC(=O)NC(C(O)=O)OCC1=CC=CC=C1 VBJNGFKLXFJKQR-UHFFFAOYSA-N 0.000 description 5
- CUVGUPIVTLGRGI-UHFFFAOYSA-N 4-(3-phosphonopropyl)piperazine-2-carboxylic acid Chemical compound OC(=O)C1CN(CCCP(O)(O)=O)CCN1 CUVGUPIVTLGRGI-UHFFFAOYSA-N 0.000 description 5
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 5
- 108010054847 carboxypeptidase P Proteins 0.000 description 5
- 229940125782 compound 2 Drugs 0.000 description 5
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 5
- OLQYOYQJNIZKEW-UHFFFAOYSA-N N(C(=N)N)CCCCCCC(=O)NC(C(=O)O)OC Chemical compound N(C(=N)N)CCCCCCC(=O)NC(C(=O)O)OC OLQYOYQJNIZKEW-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- 125000003172 aldehyde group Chemical group 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- BOFANXNIJRGZCE-UHFFFAOYSA-N 2-(methoxyamino)acetic acid Chemical compound CONCC(O)=O BOFANXNIJRGZCE-UHFFFAOYSA-N 0.000 description 2
- WLCNZYVOUPOLHO-UHFFFAOYSA-N 3-(4-aminobutylamino)propanenitrile Chemical compound NCCCCNCCC#N WLCNZYVOUPOLHO-UHFFFAOYSA-N 0.000 description 2
- PMRNAYCJSPLHQG-UHFFFAOYSA-N 9-(diaminomethylideneamino)nonanamide;hydrochloride Chemical compound Cl.NC(=N)NCCCCCCCCC(N)=O PMRNAYCJSPLHQG-UHFFFAOYSA-N 0.000 description 2
- 108010080937 Carboxypeptidases A Proteins 0.000 description 2
- 102000000496 Carboxypeptidases A Human genes 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- FPFQPLFYTKMCHN-PPHPATTJSA-N ethyl (2s)-2-amino-3-phenylpropanoate;hydron;chloride Chemical compound Cl.CCOC(=O)[C@@H](N)CC1=CC=CC=C1 FPFQPLFYTKMCHN-PPHPATTJSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229960005190 phenylalanine Drugs 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000012064 sodium phosphate buffer Substances 0.000 description 2
- VRYGRLBNIVQXMY-UHFFFAOYSA-M sodium;acetic acid;chloride Chemical compound [Na+].[Cl-].CC(O)=O VRYGRLBNIVQXMY-UHFFFAOYSA-M 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RUZVVWNYIQNHSD-UHFFFAOYSA-N 2-(phenylmethoxyamino)acetic acid Chemical compound OC(=O)CNOCC1=CC=CC=C1 RUZVVWNYIQNHSD-UHFFFAOYSA-N 0.000 description 1
- SCAHQODBSZHGTR-UHFFFAOYSA-N 2-amino-2-ethoxyacetic acid Chemical compound CCOC(N)C(O)=O SCAHQODBSZHGTR-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- UBXMNUPLKIWGQI-UHFFFAOYSA-N 3-(4-aminobutylamino)propanenitrile;dihydrochloride Chemical compound Cl.Cl.NCCCCNCCC#N UBXMNUPLKIWGQI-UHFFFAOYSA-N 0.000 description 1
- FTUSVSFXDXMXGE-UHFFFAOYSA-N 7-(diaminomethylideneamino)heptanamide;hydrochloride Chemical compound Cl.NC(=N)NCCCCCCC(N)=O FTUSVSFXDXMXGE-UHFFFAOYSA-N 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000193417 Brevibacillus laterosporus Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NPWGWQRXHVJJRD-UHFFFAOYSA-N N-hydroxyglycine Chemical compound ONCC(O)=O NPWGWQRXHVJJRD-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- XQYZOBNLCUAXLF-XRIGFGBMSA-N [(2s)-5-[[amino(azaniumyl)methylidene]amino]-1-methoxy-1-oxopentan-2-yl]azanium;dichloride Chemical compound Cl.Cl.COC(=O)[C@@H](N)CCCN=C(N)N XQYZOBNLCUAXLF-XRIGFGBMSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- ZHWLPDIRXJCEJY-UHFFFAOYSA-N alpha-hydroxyglycine Chemical compound NC(O)C(O)=O ZHWLPDIRXJCEJY-UHFFFAOYSA-N 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- MBOSILYQUUEPKC-UHFFFAOYSA-N n-[2-[4-(3-aminopropylamino)butylamino]-2-oxo-1-phenylmethoxyethyl]-7-(diaminomethylideneamino)heptanamide;trihydrochloride Chemical compound Cl.Cl.Cl.NCCCNCCCCNC(=O)C(NC(=O)CCCCCCN=C(N)N)OCC1=CC=CC=C1 MBOSILYQUUEPKC-UHFFFAOYSA-N 0.000 description 1
- NZQZZKUBOTVFFS-UHFFFAOYSA-N n-[4-(3-aminopropylamino)butyl]-2-oxoacetamide Chemical compound NCCCNCCCCNC(=O)C=O NZQZZKUBOTVFFS-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3429884A JPS60178852A (ja) | 1984-02-27 | 1984-02-27 | ω−グアニジノ脂肪酸アミド−グリオキシル酸付加体及びその製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3429884A JPS60178852A (ja) | 1984-02-27 | 1984-02-27 | ω−グアニジノ脂肪酸アミド−グリオキシル酸付加体及びその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60178852A JPS60178852A (ja) | 1985-09-12 |
| JPH0254822B2 true JPH0254822B2 (de) | 1990-11-22 |
Family
ID=12410249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3429884A Granted JPS60178852A (ja) | 1984-02-27 | 1984-02-27 | ω−グアニジノ脂肪酸アミド−グリオキシル酸付加体及びその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60178852A (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0535160Y2 (de) * | 1988-10-24 | 1993-09-07 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0990795A (ja) * | 1994-12-13 | 1997-04-04 | Ricoh Co Ltd | 画像形成装置 |
-
1984
- 1984-02-27 JP JP3429884A patent/JPS60178852A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0535160Y2 (de) * | 1988-10-24 | 1993-09-07 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60178852A (ja) | 1985-09-12 |
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