JPH11513686A - 線維素原受容体拮抗薬 - Google Patents

線維素原受容体拮抗薬

Info

Publication number: JPH11513686A
Authority: JP; Japan
Prior art keywords: ethyl; alkyl; acetyl; piperidone; pyridin
Prior art date: 1995-10-19
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.): Pending

Application number

JP9515931A

Other languages

English (en)

Japanese (ja)

Inventor

アスキユー，ベン・シー

ハートマン，ジヨージ・デイー

デユーガン，マーク・イー

ヤング，ステイーブン・デイー

ハツチンソン，ジヨン・エイチ

ウエイ，ジヨン・エス

エグバートソン，メリツサ・エス

バサロ，ローラ・エム

リビー，ローラ・エイ

アイル，ネイサン・シー

クロース，エイミー・イー

ハルチエンコ，ワジル

Original Assignee

メルクエンドカンパニーインコーポレーテッド

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.)

1995-10-19

Filing date

1996-10-15

Publication date

1999-11-24

1996-02-16 Priority claimed from GBGB9603371.7A external-priority patent/GB9603371D0/en

1996-10-15 Application filed by メルクエンドカンパニーインコーポレーテッド filed Critical メルクエンドカンパニーインコーポレーテッド

1999-11-24 Publication of JPH11513686A publication Critical patent/JPH11513686A/ja

Status Pending legal-status Critical Current

Links

239000002319 fibrinogen receptor antagonist Substances 0.000 title abstract description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 258
-1 carboxy, carboxy Chemical group 0.000 claims description 220
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 213
150000001875 compounds Chemical class 0.000 claims description 126
239000000203 mixture Substances 0.000 claims description 107
125000003118 aryl group Chemical group 0.000 claims description 81
238000000034 method Methods 0.000 claims description 71
229940000635 beta-alanine Drugs 0.000 claims description 59
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 55
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 55
239000002253 acid Substances 0.000 claims description 50
108010049003 Fibrinogen Proteins 0.000 claims description 39
102000008946 Fibrinogen Human genes 0.000 claims description 39
229940012952 fibrinogen Drugs 0.000 claims description 39
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 37
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 35
150000002148 esters Chemical class 0.000 claims description 32
235000019260 propionic acid Nutrition 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 27
241000124008 Mammalia Species 0.000 claims description 26
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 25
150000001408 amides Chemical class 0.000 claims description 23
XQZMKWNRWFUZLU-VIFPVBQESA-N (3s)-3-acetamido-3-pyridin-3-ylpropanoic acid Chemical compound CC(=O)N[C@@H](CC(O)=O)C1=CC=CN=C1 XQZMKWNRWFUZLU-VIFPVBQESA-N 0.000 claims description 22
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 21
GONZZHIQIZBCNK-SCSAIBSYSA-N (3r)-3-acetamidobutanoic acid Chemical compound OC(=O)C[C@@H](C)NC(C)=O GONZZHIQIZBCNK-SCSAIBSYSA-N 0.000 claims description 19
208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 18
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 14
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 13
125000004494 ethyl ester group Chemical group 0.000 claims description 13
238000004519 manufacturing process Methods 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
208000007536 Thrombosis Diseases 0.000 claims description 11
239000003814 drug Substances 0.000 claims description 11
LIZXVXACMCGYKE-NSHDSACASA-N ethyl (3s)-3-acetamido-3-pyridin-3-ylpropanoate Chemical compound CCOC(=O)C[C@H](NC(C)=O)C1=CC=CN=C1 LIZXVXACMCGYKE-NSHDSACASA-N 0.000 claims description 11
230000005764 inhibitory process Effects 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 11
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
BKTGEFWYDOHNFT-GFCCVEGCSA-N CC(=O)N[C@H](CCC1=CC=CC=C1)CC(=O)O Chemical compound CC(=O)N[C@H](CCC1=CC=CC=C1)CC(=O)O BKTGEFWYDOHNFT-GFCCVEGCSA-N 0.000 claims description 9
RKOTXQYWCBGZLP-UHFFFAOYSA-N N-[(2,4-difluorophenyl)methyl]-2-ethyl-9-hydroxy-3-methoxy-1,8-dioxospiro[3H-pyrido[1,2-a]pyrazine-4,3'-oxolane]-7-carboxamide Chemical compound CCN1C(OC)C2(CCOC2)N2C=C(C(=O)NCC3=C(F)C=C(F)C=C3)C(=O)C(O)=C2C1=O RKOTXQYWCBGZLP-UHFFFAOYSA-N 0.000 claims description 9
230000015572 biosynthetic process Effects 0.000 claims description 9
239000003937 drug carrier Substances 0.000 claims description 9
230000000694 effects Effects 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 8
125000004122 cyclic group Chemical group 0.000 claims description 8
229940079593 drug Drugs 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
VHOMAPWVLKRQAZ-UHFFFAOYSA-N Benzyl propionate Chemical compound CCC(=O)OCC1=CC=CC=C1 VHOMAPWVLKRQAZ-UHFFFAOYSA-N 0.000 claims description 7
150000008641 benzimidazolones Chemical class 0.000 claims description 7
PQQFEBNCOPSQEO-NSHDSACASA-N (2s)-3-acetamido-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound CC(=O)NC[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 PQQFEBNCOPSQEO-NSHDSACASA-N 0.000 claims description 6
AKOVXMLBDXLGSK-UHFFFAOYSA-N 3-acetamido-3-(4-fluorophenyl)propanoic acid Chemical compound CC(=O)NC(CC(O)=O)C1=CC=C(F)C=C1 AKOVXMLBDXLGSK-UHFFFAOYSA-N 0.000 claims description 6
LJLLAWRMBZNPMO-UHFFFAOYSA-N N-acetyl-beta-alanine Chemical compound CC(=O)NCCC(O)=O LJLLAWRMBZNPMO-UHFFFAOYSA-N 0.000 claims description 6
239000003146 anticoagulant agent Substances 0.000 claims description 6
230000015271 coagulation Effects 0.000 claims description 6
238000005345 coagulation Methods 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
238000011282 treatment Methods 0.000 claims description 6
GSCLMSFRWBPUSK-VKHMYHEASA-N (4s)-4-methyloxetan-2-one Chemical compound C[C@H]1CC(=O)O1 GSCLMSFRWBPUSK-VKHMYHEASA-N 0.000 claims description 5
MQBLDETYTPWLRC-UHFFFAOYSA-N 2-acetamido-6,6-dimethylhept-4-ynoic acid Chemical compound C(C)(=O)NC(C(=O)O)CC#CC(C)(C)C MQBLDETYTPWLRC-UHFFFAOYSA-N 0.000 claims description 5
NPXKNPYESGNBIH-UHFFFAOYSA-N 2-acetamidohex-4-ynoic acid Chemical compound CC#CCC(C(O)=O)NC(C)=O NPXKNPYESGNBIH-UHFFFAOYSA-N 0.000 claims description 5
208000005189 Embolism Diseases 0.000 claims description 5
208000001435 Thromboembolism Diseases 0.000 claims description 5
229940127218 antiplatelet drug Drugs 0.000 claims description 5
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 5
239000000106 platelet aggregation inhibitor Substances 0.000 claims description 5
150000008574 D-amino acids Chemical class 0.000 claims description 4
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 4
125000006598 aminocarbonylamino group Chemical group 0.000 claims description 4
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 4
125000001769 aryl amino group Chemical group 0.000 claims description 4
125000005141 aryl amino sulfonyl group Chemical group 0.000 claims description 4
125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 4
125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims description 4
125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
230000002265 prevention Effects 0.000 claims description 4
229960000103 thrombolytic agent Drugs 0.000 claims description 4
230000002537 thrombolytic effect Effects 0.000 claims description 4
YSPAKPPINKSOKX-BYPYZUCNSA-N (2s)-3-acetamido-2-aminopropanoic acid Chemical compound CC(=O)NC[C@H](N)C(O)=O YSPAKPPINKSOKX-BYPYZUCNSA-N 0.000 claims description 3
WKMPTGFIUPPIGN-UHFFFAOYSA-N 3-(3-fluoroanilino)propanoic acid Chemical compound OC(=O)CCNC1=CC=CC(F)=C1 WKMPTGFIUPPIGN-UHFFFAOYSA-N 0.000 claims description 3
FEJRBDFITLZBAD-UHFFFAOYSA-N 3-acetamido-3-(3-fluorophenyl)propanoic acid Chemical compound CC(=O)NC(CC(O)=O)C1=CC=CC(F)=C1 FEJRBDFITLZBAD-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
150000008575 L-amino acids Chemical class 0.000 claims description 3
229940127219 anticoagulant drug Drugs 0.000 claims description 3
MWHOKDCXWWRGCM-UHFFFAOYSA-N ethyl 3-(2-fluoroanilino)propanoate Chemical compound CCOC(=O)CCNC1=CC=CC=C1F MWHOKDCXWWRGCM-UHFFFAOYSA-N 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
125000002950 monocyclic group Chemical group 0.000 claims description 3
INIIDHXJMONHDV-UHFFFAOYSA-N tert-butyl 3-acetamidopropanoate Chemical compound CC(=O)NCCC(=O)OC(C)(C)C INIIDHXJMONHDV-UHFFFAOYSA-N 0.000 claims description 3
241000051616 Ulmus minor Species 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
125000002619 bicyclic group Chemical group 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
HPJUWFGEKJDJLE-UHFFFAOYSA-N hept-2-ene propanoic acid Chemical compound CCC(O)=O.CCCCC=CC HPJUWFGEKJDJLE-UHFFFAOYSA-N 0.000 claims description 2
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
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 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
230000001732 thrombotic effect Effects 0.000 claims description 2
230000000903 blocking effect Effects 0.000 claims 10
230000010102 embolization Effects 0.000 claims 2
JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims 1
QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 289
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 220
239000000243 solution Substances 0.000 description 163
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 156
235000019439 ethyl acetate Nutrition 0.000 description 138
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 132
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 121
238000005481 NMR spectroscopy Methods 0.000 description 112
238000006243 chemical reaction Methods 0.000 description 101
239000007787 solid Substances 0.000 description 80
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 72
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 58
238000003756 stirring Methods 0.000 description 50
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 49
239000000460 chlorine Substances 0.000 description 49
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
239000003921 oil Substances 0.000 description 43
230000002829 reductive effect Effects 0.000 description 43
239000000377 silicon dioxide Substances 0.000 description 43
239000012267 brine Substances 0.000 description 41
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 41
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 41
239000000741 silica gel Substances 0.000 description 39
229910002027 silica gel Inorganic materials 0.000 description 39
239000010410 layer Substances 0.000 description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
229920006395 saturated elastomer Polymers 0.000 description 30
239000012141 concentrate Substances 0.000 description 28
239000002904 solvent Substances 0.000 description 28
235000008504 concentrate Nutrition 0.000 description 26
238000005160 1H NMR spectroscopy Methods 0.000 description 25
238000004587 chromatography analysis Methods 0.000 description 25
108090000765 processed proteins & peptides Proteins 0.000 description 25
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 24
238000000921 elemental analysis Methods 0.000 description 22
239000012044 organic layer Substances 0.000 description 22
239000000047 product Substances 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 21
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 19
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 19
238000003818 flash chromatography Methods 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
229960000583 acetic acid Drugs 0.000 description 18
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 17
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 16
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
239000000706 filtrate Substances 0.000 description 15
239000007789 gas Substances 0.000 description 13
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 12
239000007864 aqueous solution Substances 0.000 description 12
229910052786 argon Inorganic materials 0.000 description 12
102000004196 processed proteins & peptides Human genes 0.000 description 12
238000004007 reversed phase HPLC Methods 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
239000012043 crude product Substances 0.000 description 11
238000001914 filtration Methods 0.000 description 11
239000007788 liquid Substances 0.000 description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
239000000725 suspension Substances 0.000 description 11
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
238000004440 column chromatography Methods 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
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230000002776 aggregation Effects 0.000 description 9
238000004220 aggregation Methods 0.000 description 9
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
238000009472 formulation Methods 0.000 description 9
238000004108 freeze drying Methods 0.000 description 9
238000000746 purification Methods 0.000 description 9
239000011734 sodium Substances 0.000 description 9
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229910004373 HOAc Inorganic materials 0.000 description 8
238000007792 addition Methods 0.000 description 8
210000004369 blood Anatomy 0.000 description 8
239000008280 blood Substances 0.000 description 8
238000001816 cooling Methods 0.000 description 8
239000003480 eluent Substances 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
229920001184 polypeptide Polymers 0.000 description 8
108020003175 receptors Proteins 0.000 description 8
102000005962 receptors Human genes 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 8
239000003826 tablet Substances 0.000 description 8
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IYMAXBFPHPZYIK-BQBZGAKWSA-N Arg-Gly-Asp Chemical compound NC(N)=NCCC[C@H](N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(O)=O IYMAXBFPHPZYIK-BQBZGAKWSA-N 0.000 description 7
239000012458 free base Substances 0.000 description 7
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239000000463 material Substances 0.000 description 7
239000002994 raw material Substances 0.000 description 7
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WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
229940024606 amino acid Drugs 0.000 description 6
235000001014 amino acid Nutrition 0.000 description 6
150000001413 amino acids Chemical class 0.000 description 6
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IFGCUJZIWBUILZ-UHFFFAOYSA-N sodium 2-[[2-[[hydroxy-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyphosphoryl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid Chemical compound [Na+].C=1NC2=CC=CC=C2C=1CC(C(O)=O)NC(=O)C(CC(C)C)NP(O)(=O)OC1OC(C)C(O)C(O)C1O IFGCUJZIWBUILZ-UHFFFAOYSA-N 0.000 description 1
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239000000661 sodium alginate Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
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WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
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239000012453 solvate Substances 0.000 description 1
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239000007858 starting material Substances 0.000 description 1
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239000007929 subcutaneous injection Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
238000013269 sustained drug release Methods 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
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239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
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230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
229960002898 threonine Drugs 0.000 description 1
229960004072 thrombin Drugs 0.000 description 1
238000007395 thrombosis prophylaxis Methods 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
150000003613 toluenes Chemical class 0.000 description 1
238000003325 tomography Methods 0.000 description 1
230000000699 topical effect Effects 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
108010060000 trigramin Proteins 0.000 description 1
IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 1
239000011123 type I (borosilicate glass) Substances 0.000 description 1
229960004441 tyrosine Drugs 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
230000006439 vascular pathology Effects 0.000 description 1
238000007631 vascular surgery Methods 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
229930195724 β-lactose Natural products 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
- C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Hematology (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Diabetes (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Veterinary Medicine (AREA)
Biochemistry (AREA)
Biophysics (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

JP9515931A 1995-10-19 1996-10-15 線維素原受容体拮抗薬 Pending JPH11513686A (ja)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US560295P	1995-10-19	1995-10-19
GBGB9603371.7A GB9603371D0 (en)	1996-02-16	1996-02-16	Fibrinogen receptor antagonists
GB9603371.7		1996-02-16
GB60/005,602		1996-02-16
PCT/US1996/016491 WO1997014417A1 (en)	1995-10-19	1996-10-15	Fibrinogen receptor antagonists

Publications (1)

Publication Number	Publication Date
JPH11513686A true JPH11513686A (ja)	1999-11-24

Family

ID=26308744

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP9515931A Pending JPH11513686A (ja)	1995-10-19	1996-10-15	線維素原受容体拮抗薬

Country Status (5)

Country	Link
EP (1)	EP0866705A4 (de)
JP (1)	JPH11513686A (de)
AU (1)	AU713247B2 (de)
CA (1)	CA2234967A1 (de)
WO (1)	WO1997014417A1 (de)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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JP2002507600A (ja) *	1998-03-23	2002-03-12	アベンティス・ファーマスーティカルズ・プロダクツ・インコーポレイテツド	ピペリジジニルおよびｎ−アミジノピペリジニル誘導体
JP4495896B2 (ja) *	2000-04-05	2010-07-07	第一三共株式会社	エチレンジアミン誘導体
US7880009B2 (en)	2004-05-26	2011-02-01	Eisai R&D Management Co., Ltd.	Cinnamide compound
US7923563B2 (en)	2004-10-26	2011-04-12	Eisai R&D Management Co., Ltd.	Amorphous object of cinnamide compound
WO2007058305A1 (ja) *	2005-11-18	2007-05-24	Eisai R & D Management Co., Ltd.	シンナミド誘導体の製造方法
US7897632B2 (en)	2006-03-09	2011-03-01	Eisai R&D Management Co., Ltd.	Multi-cyclic cinnamide derivatives
US7973033B2 (en)	2006-03-09	2011-07-05	Eisai R&D Management Co., Ltd.	Multi-cyclic cinnamide derivatives
US8008293B2 (en)	2007-02-28	2011-08-30	Eisai R&D Management Co., Ltd.	Bicyclic oxomorpholine derivative
US7935815B2 (en)	2007-08-31	2011-05-03	Eisai R&D Management Co., Ltd.	Imidazoyl pyridine compounds and salts thereof
US9453000B2 (en)	2007-08-31	2016-09-27	Eisai R&D Management Co., Ltd.	Polycyclic compound

Also Published As

Publication number	Publication date
WO1997014417A1 (en)	1997-04-24
EP0866705A4 (de)	1999-03-03
CA2234967A1 (en)	1997-04-24
AU713247B2 (en)	1999-11-25
AU7432296A (en)	1997-05-07
EP0866705A1 (de)	1998-09-30

Publication	Publication Date	Title
JPH11513686A (ja)	1999-11-24	線維素原受容体拮抗薬
AU712082B2 (en)	1999-10-28	Fibrinogen receptor antagonists
US5854245A (en)	1998-12-29	Fibrinogen receptor antagonists
AU719102B2 (en)	2000-05-04	Fibrinogen receptor antagonist prodrugs
CA2258093A1 (en)	1998-01-08	Fibrinogen receptor antagonists
AU713676B2 (en)	1999-12-09	Integrin receptor antagonists
JP2001518932A (ja)	2001-10-16	トロンビン阻害薬
JPH08504194A (ja)	1996-05-07	フィブリノーゲンレセプターアンタゴニスト
JP2001500864A (ja)	2001-01-23	トロンビン阻害物質
US5780480A (en)	1998-07-14	Fibrinogen receptor antagonists
US5932582A (en)	1999-08-03	Fibrinogen receptor antagonist prodrugs
US5852045A (en)	1998-12-22	Fibrinogen receptor antagonists
CA2257937A1 (en)	1998-01-08	Fibrinogen receptor antagonist prodrugs
US5952306A (en)	1999-09-14	Integrin receptor antagonists
JP2002527424A (ja)	2002-08-27	β−アラニン誘導体の新規製造法
US5494921A (en)	1996-02-27	Fibrinogen receptor antagonists
US5525617A (en)	1996-06-11	Fibrinogen receptor antagonists
US5990107A (en)	1999-11-23	Fibrinogen receptor antagonist prodrugs
US5889023A (en)	1999-03-30	Fibrinogen receptor antagonist
AU702025B2 (en)	1999-02-11	Fibrinogen receptor antagonist
GB2312895A (en)	1997-11-12	Fibrinogen receptor antagonists