JPH0587062B2 - - Google Patents

Info

Publication number: JPH0587062B2
Authority: JP; Japan
Prior art keywords: group; amino; naphthylmethyl; add; propionyl
Prior art date: 1987-09-29
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 - Lifetime

Application number

JP63236728A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0262856A (ja

Inventor

Hajime Morishima

Takashi Koike

Masato Nakano

Shugo Atsumi

Seiichi Tanaka

Kenji Matsuyama

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.)

MSD KK

Original Assignee

Banyu Phamaceutical 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.)

1987-09-29

Filing date

1988-09-21

Publication date

1993-12-15

1988-09-02 Priority claimed from EP88114374A external-priority patent/EP0309766B1/fr

1988-09-21 Application filed by Banyu Phamaceutical Co Ltd filed Critical Banyu Phamaceutical Co Ltd

1988-09-21 Priority to JP63236728A priority Critical patent/JPH0262856A/ja

1990-03-02 Publication of JPH0262856A publication Critical patent/JPH0262856A/ja

1993-12-15 Publication of JPH0587062B2 publication Critical patent/JPH0587062B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 199
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 178
-1 1-naphthylmethyl Chemical group 0.000 claims description 166
125000000217 alkyl group Chemical group 0.000 claims description 80
125000000623 heterocyclic group Chemical group 0.000 claims description 65
239000002253 acid Substances 0.000 claims description 50
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 50
150000003839 salts Chemical class 0.000 claims description 47
125000000753 cycloalkyl group Chemical group 0.000 claims description 43
125000004433 nitrogen atom Chemical group N* 0.000 claims description 36
229910052757 nitrogen Inorganic materials 0.000 claims description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
125000004430 oxygen atom Chemical group O* 0.000 claims description 21
125000004434 sulfur atom Chemical group 0.000 claims description 20
ICICNJHEULTQLY-KRALYZGHSA-N (2s)-2-[[(2s)-2-(tert-butylsulfonylmethyl)-3-naphthalen-1-ylpropanoyl]amino]-n-[(2s,3r,4s)-1-cyclohexyl-3,4-dihydroxy-5-morpholin-4-ylpentan-2-yl]hexanamide Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)[C@H](CC=1C2=CC=CC=C2C=CC=1)CS(=O)(=O)C(C)(C)C)CCCC)[C@@H](O)[C@@H](O)CN1CCOCC1)C1CCCCC1 ICICNJHEULTQLY-KRALYZGHSA-N 0.000 claims description 19
125000003118 aryl group Chemical group 0.000 claims description 19
125000005842 heteroatom Chemical group 0.000 claims description 15
125000002950 monocyclic group Chemical group 0.000 claims description 15
125000003710 aryl alkyl group Chemical group 0.000 claims description 14
125000001424 substituent group Chemical group 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 12
125000004414 alkyl thio group Chemical group 0.000 claims description 12
125000003277 amino group Chemical group 0.000 claims description 11
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 10
125000004423 acyloxy group Chemical group 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 9
150000001413 amino acids Chemical class 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 6
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 5
125000002619 bicyclic group Chemical group 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
KZOGVMNRYWJRME-UHFFFAOYSA-N 1-amino-5-cyclohexyl-1-morpholin-4-ylpentane-2,3-diol Chemical compound C1COCCN1C(N)C(O)C(O)CCC1CCCCC1 KZOGVMNRYWJRME-UHFFFAOYSA-N 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 4
239000002220 antihypertensive agent Substances 0.000 claims description 4
125000004442 acylamino group Chemical group 0.000 claims description 3
125000002072 seryl group Chemical group 0.000 claims description 3
125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
LTICUUBGIZYYAU-CLZHSDMDSA-N (2s)-n-[(2s,3r,4s)-1-cyclohexyl-3,4-dihydroxy-5-morpholin-4-ylpentan-2-yl]-2-[[(2s)-2-(furan-2-ylmethylsulfonylmethyl)-3-naphthalen-1-ylpropanoyl]amino]hexanamide Chemical compound C([C@@H](CC=1C2=CC=CC=C2C=CC=1)C(=O)N[C@@H](CCCC)C(=O)N[C@@H](CC1CCCCC1)[C@@H](O)[C@@H](O)CN1CCOCC1)S(=O)(=O)CC1=CC=CO1 LTICUUBGIZYYAU-CLZHSDMDSA-N 0.000 claims description 2
WDTSFELOIFOXMS-RNPUFIIPSA-N (2s)-n-[(2s,3r,4s)-1-cyclohexyl-3,4-dihydroxy-5-morpholin-4-ylpentan-2-yl]-4-methyl-2-[[(2s)-2-(propan-2-ylsulfonylmethyl)-3-quinolin-8-ylpropanoyl]amino]pentanamide Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)[C@H](CC=1C2=NC=CC=C2C=CC=1)CS(=O)(=O)C(C)C)CC(C)C)[C@@H](O)[C@@H](O)CN1CCOCC1)C1CCCCC1 WDTSFELOIFOXMS-RNPUFIIPSA-N 0.000 claims description 2
WDXBQRUGPJZRKT-LJHWHBDJSA-N (2s)-2-[[(2s)-2-benzyl-3-(furan-2-ylmethylsulfonyl)propanoyl]amino]-n-[(2s,3r,4s)-1-cyclohexyl-3,4-dihydroxy-5-morpholin-4-ylpentan-2-yl]hexanamide Chemical compound C([C@@H](C(=O)N[C@@H](CCCC)C(=O)N[C@@H](CC1CCCCC1)[C@@H](O)[C@@H](O)CN1CCOCC1)CS(=O)(=O)CC=1OC=CC=1)C1=CC=CC=C1 WDXBQRUGPJZRKT-LJHWHBDJSA-N 0.000 claims 1
MAXSDJUORSCIRM-LJHWHBDJSA-N (2s)-2-[[(2s)-2-benzyl-3-cyclopentylsulfonylpropanoyl]amino]-n-[(2s,3r,4s)-1-cyclohexyl-3,4-dihydroxy-5-(4-oxidomorpholin-4-ium-4-yl)pentan-2-yl]hexanamide Chemical compound C([C@@H](C(=O)N[C@@H](CCCC)C(=O)N[C@@H](CC1CCCCC1)[C@@H](O)[C@@H](O)C[N+]1([O-])CCOCC1)CS(=O)(=O)C1CCCC1)C1=CC=CC=C1 MAXSDJUORSCIRM-LJHWHBDJSA-N 0.000 claims 1
IKZGESODNCALLW-GCIGRYLYSA-N (2s)-2-[[(2s)-2-benzyl-3-pyrimidin-2-ylsulfonylpropanoyl]amino]-n-[(2s,3r,4s)-1-cyclohexyl-3,4-dihydroxy-5-morpholin-4-ylpentan-2-yl]hexanamide Chemical compound C([C@@H](C(=O)N[C@@H](CCCC)C(=O)N[C@@H](CC1CCCCC1)[C@@H](O)[C@@H](O)CN1CCOCC1)CS(=O)(=O)C=1N=CC=CN=1)C1=CC=CC=C1 IKZGESODNCALLW-GCIGRYLYSA-N 0.000 claims 1
SUIGKVKRDQITIT-BTWQBLKXSA-N (2s)-n-[(2s)-1-[[(2s,3r,4s)-1-cyclohexyl-3,4-dihydroxy-5-morpholin-4-ylpentan-2-yl]amino]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]-2-(ethylsulfonylmethyl)-3-naphthalen-1-ylpropanamide Chemical compound C([C@H](NC(=O)[C@H](CC=1C2=CC=CC=C2C=CC=1)CS(=O)(=O)CC)C(=O)N[C@@H](CC1CCCCC1)[C@@H](O)[C@@H](O)CN1CCOCC1)C1=CN=CN1 SUIGKVKRDQITIT-BTWQBLKXSA-N 0.000 claims 1
LDMRAHMPQWKRIK-ITUQMYGTSA-N (2s)-n-[(2s)-1-[[(2s,3r,4s)-1-cyclohexyl-3,4-dihydroxy-5-morpholin-4-ylpentan-2-yl]amino]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]-2-(naphthalen-1-ylmethyl)-3-propan-2-ylsulfinylpropanamide Chemical compound C([C@H](NC(=O)[C@H](CC=1C2=CC=CC=C2C=CC=1)CS(=O)C(C)C)C(=O)N[C@@H](CC1CCCCC1)[C@@H](O)[C@@H](O)CN1CCOCC1)C1=CN=CN1 LDMRAHMPQWKRIK-ITUQMYGTSA-N 0.000 claims 1
BLBQAONVMIHHMA-DFRGSZQTSA-N (2s)-n-[(2s)-1-cyclohexyl-3,4-dihydroxy-5-morpholin-4-ylpentan-2-yl]-2-[[2-(ethylsulfonylmethyl)-3-naphthalen-1-ylpropanoyl]amino]hexanamide Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)C(CC=1C2=CC=CC=C2C=CC=1)CS(=O)(=O)CC)CCCC)C(O)C(O)CN1CCOCC1)C1CCCCC1 BLBQAONVMIHHMA-DFRGSZQTSA-N 0.000 claims 1
NFTBZCHHUHQJRY-LPYGFTEJSA-N (2s)-n-[(2s)-1-cyclohexyl-5-[ethyl(2-hydroxyethyl)amino]-3,4-dihydroxypentan-2-yl]-2-[[(2s)-2-(ethylsulfonylmethyl)-3-naphthalen-1-ylpropanoyl]amino]hexanamide Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)[C@H](CC=1C2=CC=CC=C2C=CC=1)CS(=O)(=O)CC)CCCC)C(O)C(O)CN(CC)CCO)C1CCCCC1 NFTBZCHHUHQJRY-LPYGFTEJSA-N 0.000 claims 1
WTMNFNLILAKIMY-KRALYZGHSA-N (2s)-n-[(2s,3r,4s)-1-cyclohexyl-3,4-dihydroxy-5-(1-oxidopiperidin-1-ium-1-yl)pentan-2-yl]-2-[[(2s)-2-(ethylsulfonylmethyl)-3-naphthalen-1-ylpropanoyl]amino]hexanamide Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)[C@H](CC=1C2=CC=CC=C2C=CC=1)CS(=O)(=O)CC)CCCC)[C@@H](O)[C@@H](O)C[N+]1([O-])CCCCC1)C1CCCCC1 WTMNFNLILAKIMY-KRALYZGHSA-N 0.000 claims 1
HMKKDXIKCDIFTD-HOQQKOLYSA-N (2s)-n-[(2s,3r,4s)-1-cyclohexyl-3,4-dihydroxy-5-(2-hydroxyethylamino)pentan-2-yl]-2-[[(2s)-2-(ethylsulfonylmethyl)-3-naphthalen-1-ylpropanoyl]amino]hexanamide Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)[C@H](CC=1C2=CC=CC=C2C=CC=1)CS(=O)(=O)CC)CCCC)[C@@H](O)[C@@H](O)CNCCO)C1CCCCC1 HMKKDXIKCDIFTD-HOQQKOLYSA-N 0.000 claims 1
QWTXTVKRDMQQOT-LJHWHBDJSA-N (2s)-n-[(2s,3r,4s)-1-cyclohexyl-3,4-dihydroxy-5-(2-methoxyethylamino)pentan-2-yl]-2-[[(2s)-2-(ethylsulfonylmethyl)-3-naphthalen-1-ylpropanoyl]amino]hexanamide Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)[C@H](CC=1C2=CC=CC=C2C=CC=1)CS(=O)(=O)CC)CCCC)[C@@H](O)[C@@H](O)CNCCOC)C1CCCCC1 QWTXTVKRDMQQOT-LJHWHBDJSA-N 0.000 claims 1
WWMGAEUQBJAZDY-VOLCAMQRSA-N (2s)-n-[(2s,3r,4s)-1-cyclohexyl-3,4-dihydroxy-5-(4-methylpiperidin-1-yl)pentan-2-yl]-2-[[(2s)-2-(ethylsulfonylmethyl)-3-naphthalen-1-ylpropanoyl]amino]hexanamide Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)[C@H](CC=1C2=CC=CC=C2C=CC=1)CS(=O)(=O)CC)CCCC)[C@@H](O)[C@@H](O)CN1CCC(C)CC1)C1CCCCC1 WWMGAEUQBJAZDY-VOLCAMQRSA-N 0.000 claims 1
SBSKVDFNWYHFQP-RERVPDENSA-N (2s)-n-[(2s,3r,4s)-1-cyclohexyl-3,4-dihydroxy-5-morpholin-4-ylpentan-2-yl]-2-[[(2s)-2-(ethylsulfinylmethyl)-3-naphthalen-1-ylpropanoyl]amino]hexanamide Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)[C@H](CC=1C2=CC=CC=C2C=CC=1)CS(=O)CC)CCCC)[C@@H](O)[C@@H](O)CN1CCOCC1)C1CCCCC1 SBSKVDFNWYHFQP-RERVPDENSA-N 0.000 claims 1
VTELBQOMIKBAQA-GCIGRYLYSA-N (2s)-n-[(2s,3r,4s)-1-cyclohexyl-3,4-dihydroxy-5-morpholin-4-ylpentan-2-yl]-2-[[(2s)-2-(ethylsulfonylmethyl)-3-(3-methylphenyl)propanoyl]amino]hexanamide Chemical compound C([C@@H](C(=O)N[C@@H](CCCC)C(=O)N[C@@H](CC1CCCCC1)[C@@H](O)[C@@H](O)CN1CCOCC1)CS(=O)(=O)CC)C1=CC=CC(C)=C1 VTELBQOMIKBAQA-GCIGRYLYSA-N 0.000 claims 1
DQZAUYUJOYXOQT-QQEJMDCYSA-N (2s)-n-[(2s,3r,4s)-1-cyclohexyl-3,4-dihydroxy-5-morpholin-4-ylpentan-2-yl]-2-[[(2s)-2-(ethylsulfonylmethyl)-3-(5,6,7,8-tetrahydronaphthalen-1-yl)propanoyl]amino]hexanamide Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)[C@H](CC=1C=2CCCCC=2C=CC=1)CS(=O)(=O)CC)CCCC)[C@@H](O)[C@@H](O)CN1CCOCC1)C1CCCCC1 DQZAUYUJOYXOQT-QQEJMDCYSA-N 0.000 claims 1
AQZARKHGAHCNTN-LJHWHBDJSA-N (2s)-n-[(2s,3r,4s)-1-cyclohexyl-3,4-dihydroxy-5-morpholin-4-ylpentan-2-yl]-2-[[(2s)-2-(ethylsulfonylmethyl)-3-naphthalen-1-ylpropanoyl]amino]-4-methylsulfanylbutanamide Chemical compound C([C@H](NC(=O)[C@H](CCSC)NC(=O)[C@H](CC=1C2=CC=CC=C2C=CC=1)CS(=O)(=O)CC)[C@@H](O)[C@@H](O)CN1CCOCC1)C1CCCCC1 AQZARKHGAHCNTN-LJHWHBDJSA-N 0.000 claims 1
SOHDKPLFSIXCCB-KAAJUZHGSA-N (2s)-n-[(2s,3r,4s)-1-cyclohexyl-3,4-dihydroxy-5-morpholin-4-ylpentan-2-yl]-2-[[(2s)-2-(ethylsulfonylmethyl)-3-quinolin-8-ylpropanoyl]amino]hexanamide Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)[C@H](CC=1C2=NC=CC=C2C=CC=1)CS(=O)(=O)CC)CCCC)[C@@H](O)[C@@H](O)CN1CCOCC1)C1CCCCC1 SOHDKPLFSIXCCB-KAAJUZHGSA-N 0.000 claims 1
QXKZVIIRXRCFPG-NTXHHJEXSA-N (2s)-n-[(2s,3r,4s)-1-cyclohexyl-3,4-dihydroxy-5-morpholin-4-ylpentan-2-yl]-2-[[(2s)-2-(naphthalen-1-ylmethyl)-3-pyrimidin-2-ylpropanethioyl]amino]hexanamide Chemical compound C([C@@H](C(=S)N[C@@H](CCCC)C(=O)N[C@@H](CC1CCCCC1)[C@@H](O)[C@@H](O)CN1CCOCC1)CC=1C2=CC=CC=C2C=CC=1)C1=NC=CC=N1 QXKZVIIRXRCFPG-NTXHHJEXSA-N 0.000 claims 1
XGQLSOUSWAXTLW-KRALYZGHSA-N (2s)-n-[(2s,3r,4s)-1-cyclohexyl-3,4-dihydroxy-5-piperidin-1-ylpentan-2-yl]-2-[[(2s)-2-(ethylsulfonylmethyl)-3-naphthalen-1-ylpropanoyl]amino]hexanamide Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)[C@H](CC=1C2=CC=CC=C2C=CC=1)CS(=O)(=O)CC)CCCC)[C@@H](O)[C@@H](O)CN1CCCCC1)C1CCCCC1 XGQLSOUSWAXTLW-KRALYZGHSA-N 0.000 claims 1
NBSQXDTVPUCLPL-QQEJMDCYSA-N (2s)-n-[(2s,3r,4s)-1-cyclohexyl-5-(diethylamino)-3,4-dihydroxypentan-2-yl]-2-[[(2s)-2-(ethylsulfonylmethyl)-3-naphthalen-1-ylpropanoyl]amino]hexanamide Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)[C@H](CC=1C2=CC=CC=C2C=CC=1)CS(=O)(=O)CC)CCCC)[C@@H](O)[C@@H](O)CN(CC)CC)C1CCCCC1 NBSQXDTVPUCLPL-QQEJMDCYSA-N 0.000 claims 1
BZEWYDLZRQIHCF-QMVABORWSA-N (2s)-n-[(2s,3r,4s)-2,3-dihydroxy-6-methyl-1-morpholin-4-ylheptan-4-yl]-2-[[(2s)-2-(ethylsulfonylmethyl)-3-naphthalen-1-ylpropanoyl]amino]hexanamide Chemical compound C([C@H](O)[C@H](O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC=1C2=CC=CC=C2C=CC=1)CS(=O)(=O)CC)CCCC)N1CCOCC1 BZEWYDLZRQIHCF-QMVABORWSA-N 0.000 claims 1
RCGQGPNDOYXDOL-QQEJMDCYSA-N [(3s)-4-[[(2s,3r,4s)-1-cyclohexyl-3,4-dihydroxy-5-morpholin-4-ylpentan-2-yl]amino]-3-[[(2s)-2-(ethylsulfonylmethyl)-3-naphthalen-1-ylpropanoyl]amino]-4-oxobutyl] acetate Chemical compound C([C@H](NC(=O)[C@H](CCOC(C)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2C=CC=1)CS(=O)(=O)CC)[C@@H](O)[C@@H](O)CN1CCOCC1)C1CCCCC1 RCGQGPNDOYXDOL-QQEJMDCYSA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 461
239000000243 solution Substances 0.000 description 255
238000003756 stirring Methods 0.000 description 254
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 244
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 214
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 212
230000002829 reductive effect Effects 0.000 description 184
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 176
239000002904 solvent Substances 0.000 description 174
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 150
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 147
238000006243 chemical reaction Methods 0.000 description 145
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 131
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 130
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 123
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 113
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 95
238000005481 NMR spectroscopy Methods 0.000 description 93
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 87
239000012230 colorless oil Substances 0.000 description 87
238000001035 drying Methods 0.000 description 80
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 78
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 78
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 76
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 74
238000010898 silica gel chromatography Methods 0.000 description 69
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 68
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 67
239000010410 layer Substances 0.000 description 67
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 66
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 65
238000000034 method Methods 0.000 description 62
LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 description 56
238000001819 mass spectrum Methods 0.000 description 53
239000007864 aqueous solution Substances 0.000 description 52
235000019441 ethanol Nutrition 0.000 description 51
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 46
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 46
239000000741 silica gel Substances 0.000 description 45
229910002027 silica gel Inorganic materials 0.000 description 45
239000007787 solid Substances 0.000 description 45
150000002148 esters Chemical class 0.000 description 44
238000005406 washing Methods 0.000 description 44
239000000843 powder Substances 0.000 description 41
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 39
229960000583 acetic acid Drugs 0.000 description 39
239000000284 extract Substances 0.000 description 39
235000011054 acetic acid Nutrition 0.000 description 36
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 35
239000012044 organic layer Substances 0.000 description 35
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CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229960001783 nicardipine Drugs 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
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229960001597 nifedipine Drugs 0.000 description 1
229960000715 nimodipine Drugs 0.000 description 1
229910017464 nitrogen compound Inorganic materials 0.000 description 1
150000002830 nitrogen compounds Chemical class 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
YEOYIHHNQWZEMA-UHFFFAOYSA-N o-ethyl 2-benzylpentanethioate Chemical compound CCOC(=S)C(CCC)CC1=CC=CC=C1 YEOYIHHNQWZEMA-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
239000012285 osmium tetroxide Substances 0.000 description 1
229910000489 osmium tetroxide Inorganic materials 0.000 description 1
230000001151 other effect Effects 0.000 description 1
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125000002971 oxazolyl group Chemical group 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 1
229960003540 oxyquinoline Drugs 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000005192 partition Methods 0.000 description 1
ICMWSAALRSINTC-UHFFFAOYSA-N penta-1,4-dien-3-ol Chemical compound C=CC(O)C=C ICMWSAALRSINTC-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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210000005259 peripheral blood Anatomy 0.000 description 1
239000011886 peripheral blood Substances 0.000 description 1
230000036513 peripheral conductance Effects 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
229960005190 phenylalanine Drugs 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
229920001184 polypeptide Polymers 0.000 description 1
238000012805 post-processing Methods 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
ROOVLFNJAKJSEI-UHFFFAOYSA-M potassium;ethanol;hydroxide;hydrate Chemical compound O.[OH-].[K+].CCO ROOVLFNJAKJSEI-UHFFFAOYSA-M 0.000 description 1
CASUWPDYGGAUQV-UHFFFAOYSA-M potassium;methanol;hydroxide Chemical compound [OH-].[K+].OC CASUWPDYGGAUQV-UHFFFAOYSA-M 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
238000012545 processing Methods 0.000 description 1
229960003712 propranolol Drugs 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000004088 pulmonary circulation Effects 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
238000003127 radioimmunoassay Methods 0.000 description 1
230000009103 reabsorption Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
210000002796 renal vein Anatomy 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 description 1
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
229940100890 silver compound Drugs 0.000 description 1
150000003379 silver compounds Chemical class 0.000 description 1
229910001923 silver oxide Inorganic materials 0.000 description 1
CLDWGXZGFUNWKB-UHFFFAOYSA-M silver;benzoate Chemical compound [Ag+].[O-]C(=O)C1=CC=CC=C1 CLDWGXZGFUNWKB-UHFFFAOYSA-M 0.000 description 1
210000002460 smooth muscle Anatomy 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
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000011697 sodium iodate Substances 0.000 description 1
235000015281 sodium iodate Nutrition 0.000 description 1
229940032753 sodium iodate Drugs 0.000 description 1
KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
229910001948 sodium oxide Inorganic materials 0.000 description 1
239000012064 sodium phosphate buffer Substances 0.000 description 1
229960004025 sodium salicylate Drugs 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
FRAKPAVZKUGWSR-UHFFFAOYSA-M sodium;bromite;trihydrate Chemical compound O.O.O.[Na+].[O-]Br=O FRAKPAVZKUGWSR-UHFFFAOYSA-M 0.000 description 1
WZWGGYFEOBVNLA-UHFFFAOYSA-N sodium;dihydrate Chemical compound O.O.[Na] WZWGGYFEOBVNLA-UHFFFAOYSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
238000009495 sugar coating Methods 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
230000001839 systemic circulation Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
RVTIFZBFXAHJTH-ZVAWYAOSSA-N tert-butyl (2s)-2-[(2-benzyl-3-ethoxy-3-oxopropanoyl)amino]hexanoate Chemical compound CCCC[C@@H](C(=O)OC(C)(C)C)NC(=O)C(C(=O)OCC)CC1=CC=CC=C1 RVTIFZBFXAHJTH-ZVAWYAOSSA-N 0.000 description 1
HFORXYBQJVPDTQ-VUWPPUDQSA-N tert-butyl n-[(4s)-3-hydroxy-6-methylhept-1-en-4-yl]carbamate Chemical compound CC(C)C[C@@H](C(O)C=C)NC(=O)OC(C)(C)C HFORXYBQJVPDTQ-VUWPPUDQSA-N 0.000 description 1
FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
101150002091 tfa1 gene Proteins 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
238000005732 thioetherification reaction Methods 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
238000006177 thiolation reaction Methods 0.000 description 1
125000005505 thiomorpholino group Chemical group 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
229960004605 timolol Drugs 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
210000005239 tubule Anatomy 0.000 description 1
CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
210000003556 vascular endothelial cell Anatomy 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
229960001722 verapamil Drugs 0.000 description 1
239000002699 waste material Substances 0.000 description 1
ORQXBVXKBGUSBA-QMMMGPOBSA-N β-cyclohexyl-alanine Chemical compound OC(=O)[C@@H](N)CC1CCCCC1 ORQXBVXKBGUSBA-QMMMGPOBSA-N 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Quinoline Compounds (AREA)
Pyrrole Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Hydrogenated Pyridines (AREA)
Pyridine Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Saccharide Compounds (AREA)

JP63236728A 1987-09-29 1988-09-21 新規ｎ−アシルアミノ酸誘導体及びその用途 Granted JPH0262856A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP63236728A JPH0262856A (ja)	1987-09-29	1988-09-21	新規ｎ−アシルアミノ酸誘導体及びその用途

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP24493487		1987-09-29
EP88114374.7		1988-09-02
EP88114374A EP0309766B1 (fr)	1987-09-29	1988-09-02	Dérivés N-acylés d'aminoacides et leur utilisation
JP63236728A JPH0262856A (ja)	1987-09-29	1988-09-21	新規ｎ−アシルアミノ酸誘導体及びその用途

Publications (2)

Publication Number	Publication Date
JPH0262856A JPH0262856A (ja)	1990-03-02
JPH0587062B2 true JPH0587062B2 (fr)	1993-12-15

Family

ID=26114417

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP63236728A Granted JPH0262856A (ja)	1987-09-29	1988-09-21	新規ｎ−アシルアミノ酸誘導体及びその用途

Country Status (1)

Country	Link
JP (1)	JPH0262856A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6002536A (en)	1990-07-06	1999-12-14	Hitachi Ltd.	Digital transmission signal processing system and recording/reproducing system

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0236734A2 (fr) *	1986-02-07	1987-09-16	Ciba-Geigy Ag	Dérivés d'amino-5-hydroxy-4-valeryl substitués par des groupes contenant du soufre

1988
- 1988-09-21 JP JP63236728A patent/JPH0262856A/ja active Granted

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0236734A2 (fr) *	1986-02-07	1987-09-16	Ciba-Geigy Ag	Dérivés d'amino-5-hydroxy-4-valeryl substitués par des groupes contenant du soufre

Also Published As

Publication number	Publication date
JPH0262856A (ja)	1990-03-02

Publication	Publication Date	Title
EP0309766B1 (fr)	1998-04-15	Dérivés N-acylés d'aminoacides et leur utilisation
CA1328333C (fr)	1994-04-05	Derives d'acide amine
JP3569550B2 (ja)	2004-09-22	縮合二環式環含有化合物およびその製造法
CN103402996B (zh)	2015-02-11	可用于治疗年龄相关性黄斑变性(amd)的吲哚化合物或其类似物
PT96234A (pt)	1991-10-15	Agentes inibidores da protease de hiv uteis no tratamento da sida
WO1995009864A1 (fr)	1995-04-13	Nouveau derive peptidique
WO1993003054A1 (fr)	1993-02-18	Nouveau derive de tetrapeptide
CA2263932A1 (fr)	1998-03-05	Inhibiteurs 1,4-heterocycliques de metalloproteases
EP0696593A2 (fr)	1996-02-14	Inhibiteurs de la farnesyl protéine transférase
WO2008053913A1 (fr)	2008-05-08	Dérivé de sulfonylurée capable d'inhiber sélectivement mmp-13
CA2885973C (fr)	2017-09-05	Derive de dolastatine-10, procede pour le produire et composition de medicament anticancereux le contenant
JP3464498B2 (ja)	2003-11-10	抗ｈｉｖ活性イミダゾール誘導体
WO2000044770A1 (fr)	2000-08-03	Derives phenethylamine substitues
DE69610145T2 (de)	2001-06-07	Benzo-kondensierte Azepinon-und Piperidinonverbindungen, nützlich als ACE-und NEP-Inhibitoren
DE69304573T2 (de)	1997-03-20	Aminsäurederivate mit antithrombotischer Wirkung
PT94492A (pt)	1991-04-18	Processo para a preparacao de acidos carboxilicos ( arilsulfonamido- e piridil-ou imidazolil- )-substituidos e de seus derivados
WO1997009066A1 (fr)	1997-03-13	INHIBITEUR DE SOLUBILISATION DE LIGAND Fas
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DE60009260T2 (de)	2004-08-05	Thiopyranderivate as mmp-inhibitoren
JPH10505582A (ja)	1998-06-02	ジフルオロスタトン抗ウイルス剤
JPH0587062B2 (fr)	1993-12-15
JP2943191B2 (ja)	1999-08-30	Ｎ―置換アシルアミノ酸誘導体
US5240924A (en)	1993-08-31	N-acylamino acid derivatives and their use
JP2818919B2 (ja)	1998-10-30	テトラヒドロチオフェン誘導体
JP4503833B2 (ja)	2010-07-14	高度に置換された異性体純粋なアザ環式化合物の立体化学的に制御された製造方法