JP2000502704A - ビトロネクチン受容体拮抗物質 - Google Patents

ビトロネクチン受容体拮抗物質

Info

Publication number: JP2000502704A
Authority: JP; Japan
Prior art keywords: amino; ethyl; pyridinyl; compound; alkyl
Prior art date: 1995-12-29
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.): Pending

Application number

JP9524453A

Other languages

English (en)

Japanese (ja)

Inventor

アリ，ファディア・イー

ボンディネル，ウィリアム・イー

キーナン，リチャード・エム

ク，トーマス・ウェン・フ

ミラー，ウィリアム・エイチ

サマネン，ジェイムズ

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.)

SmithKline Beecham Corp

Original Assignee

SmithKline Beecham Corp

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.)

1995-12-29

Filing date

1996-12-20

Publication date

2000-03-07

1996-12-20 Application filed by SmithKline Beecham Corp filed Critical SmithKline Beecham Corp

2000-03-07 Publication of JP2000502704A publication Critical patent/JP2000502704A/ja

Status Pending legal-status Critical Current

Links

102100022337 Integrin alpha-V Human genes 0.000 title claims abstract description 21
108010048673 Vitronectin Receptors Proteins 0.000 title claims abstract description 21
239000002464 receptor antagonist Substances 0.000 title abstract description 7
229940044551 receptor antagonist Drugs 0.000 title abstract description 7
125000000217 alkyl group Chemical group 0.000 claims abstract description 27
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 21
229910052786 argon Inorganic materials 0.000 claims abstract description 18
229910052799 carbon Inorganic materials 0.000 claims abstract description 12
229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
150000003839 salts Chemical class 0.000 claims abstract description 12
229940122331 Fibrinogen antagonist Drugs 0.000 claims abstract description 8
208000001132 Osteoporosis Diseases 0.000 claims abstract description 8
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 7
125000001475 halogen functional group Chemical group 0.000 claims abstract 4
150000001875 compounds Chemical class 0.000 claims description 441
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 243
238000002360 preparation method Methods 0.000 claims description 217
-1 2-pyridinyl Chemical group 0.000 claims description 192
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 149
238000000034 method Methods 0.000 claims description 107
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 96
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 60
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 42
239000002253 acid Substances 0.000 claims description 42
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 32
125000004076 pyridyl group Chemical group 0.000 claims description 31
238000004519 manufacturing process Methods 0.000 claims description 29
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 25
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 23
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
229960000583 acetic acid Drugs 0.000 claims description 18
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
102000005962 receptors Human genes 0.000 claims description 13
108020003175 receptors Proteins 0.000 claims description 13
230000002378 acidificating effect Effects 0.000 claims description 12
239000003814 drug Substances 0.000 claims description 12
201000001320 Atherosclerosis Diseases 0.000 claims description 10
235000019260 propionic acid Nutrition 0.000 claims description 10
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 10
208000037803 restenosis Diseases 0.000 claims description 10
206010028980 Neoplasm Diseases 0.000 claims description 8
230000005764 inhibitory process Effects 0.000 claims description 8
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims description 8
206010061218 Inflammation Diseases 0.000 claims description 6
241001024304 Mino Species 0.000 claims description 6
201000011510 cancer Diseases 0.000 claims description 6
LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical compound OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 claims description 6
230000004054 inflammatory process Effects 0.000 claims description 6
125000006239 protecting 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 5
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
125000002098 pyridazinyl group Chemical group 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 4
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 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
HHGJSOAYVHZIMK-UHFFFAOYSA-N 2-butoxy-2-phenylpropanoic acid Chemical compound CCCCOC(C)(C(O)=O)C1=CC=CC=C1 HHGJSOAYVHZIMK-UHFFFAOYSA-N 0.000 claims description 2
230000033115 angiogenesis Effects 0.000 claims description 2
QQMDYJFMRYWZKP-UHFFFAOYSA-N 2-[1-hydroxy-4-[4-[3-(pyridin-2-ylamino)propyl]piperazin-1-yl]cyclohexyl]acetic acid Chemical compound C1CC(CC(=O)O)(O)CCC1N1CCN(CCCNC=2N=CC=CC=2)CC1 QQMDYJFMRYWZKP-UHFFFAOYSA-N 0.000 claims 1
ZYLASKWUHMGCCM-UHFFFAOYSA-N 2-[6-[2-(pyridin-2-ylamino)ethylcarbamoyl]-3,4-dihydro-1h-isoquinolin-2-yl]acetic acid Chemical compound C=1C=C2CN(CC(=O)O)CCC2=CC=1C(=O)NCCNC1=CC=CC=N1 ZYLASKWUHMGCCM-UHFFFAOYSA-N 0.000 claims 1
241000124008 Mammalia Species 0.000 claims 1
230000008485 antagonism Effects 0.000 claims 1
125000000524 functional group Chemical group 0.000 claims 1
230000001575 pathological effect Effects 0.000 claims 1
230000001629 suppression Effects 0.000 claims 1
229910002091 carbon monoxide Inorganic materials 0.000 abstract description 12
229910052739 hydrogen Inorganic materials 0.000 abstract description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 132
239000000243 solution Substances 0.000 description 127
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 125
238000006243 chemical reaction Methods 0.000 description 113
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 102
239000000203 mixture Substances 0.000 description 91
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 87
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 75
239000012141 concentrate Substances 0.000 description 70
235000008504 concentrate Nutrition 0.000 description 69
239000000741 silica gel Substances 0.000 description 67
229910002027 silica gel Inorganic materials 0.000 description 67
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 64
235000019439 ethyl acetate Nutrition 0.000 description 57
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 56
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 54
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 50
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 48
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 43
229910000041 hydrogen chloride Inorganic materials 0.000 description 43
238000003756 stirring Methods 0.000 description 42
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 40
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 39
229910052763 palladium Inorganic materials 0.000 description 37
238000004587 chromatography analysis Methods 0.000 description 34
239000012044 organic layer Substances 0.000 description 33
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 33
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 30
108010012088 Fibrinogen Receptors Proteins 0.000 description 26
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 26
239000007787 solid Substances 0.000 description 26
210000004027 cell Anatomy 0.000 description 25
239000003921 oil Substances 0.000 description 24
239000011734 sodium Substances 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
239000000284 extract Substances 0.000 description 23
235000019198 oils Nutrition 0.000 description 23
239000010410 layer Substances 0.000 description 21
XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 20
239000005557 antagonist Substances 0.000 description 20
150000001732 carboxylic acid derivatives Chemical class 0.000 description 20
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 19
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 18
MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 18
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 18
239000002904 solvent Substances 0.000 description 18
TYHXIJJQIJKFSO-UHFFFAOYSA-N n'-pyridin-2-ylethane-1,2-diamine Chemical compound NCCNC1=CC=CC=N1 TYHXIJJQIJKFSO-UHFFFAOYSA-N 0.000 description 17
238000010992 reflux Methods 0.000 description 17
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
150000001412 amines Chemical class 0.000 description 15
239000002319 fibrinogen receptor antagonist Substances 0.000 description 14
210000002997 osteoclast Anatomy 0.000 description 14
239000000126 substance Substances 0.000 description 14
IDWUSJOEYZAKSW-UHFFFAOYSA-N 3-(pyridin-1-ium-2-ylamino)propanoate Chemical compound OC(=O)CCNC1=CC=CC=N1 IDWUSJOEYZAKSW-UHFFFAOYSA-N 0.000 description 13
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
239000000872 buffer Substances 0.000 description 13
239000007788 liquid Substances 0.000 description 13
108090000765 processed proteins & peptides Proteins 0.000 description 13
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
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150000002148 esters Chemical class 0.000 description 12
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 12
239000002609 medium Substances 0.000 description 12
239000000047 product Substances 0.000 description 12
YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 11
150000001408 amides Chemical class 0.000 description 11
229910000104 sodium hydride Inorganic materials 0.000 description 11
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
108010031318 Vitronectin Proteins 0.000 description 10
102100035140 Vitronectin Human genes 0.000 description 10
239000002585 base Substances 0.000 description 10
239000012267 brine Substances 0.000 description 10
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125000001424 substituent group Chemical group 0.000 description 10
241000700159 Rattus Species 0.000 description 9
239000003153 chemical reaction reagent Substances 0.000 description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
239000000543 intermediate Substances 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 9
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 8
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230000027455 binding Effects 0.000 description 8
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238000001914 filtration Methods 0.000 description 8
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208000006386 Bone Resorption Diseases 0.000 description 7
238000005481 NMR spectroscopy Methods 0.000 description 7
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
229940000635 beta-alanine Drugs 0.000 description 7
210000000988 bone and bone Anatomy 0.000 description 7
230000024279 bone resorption Effects 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 7
238000002474 experimental method Methods 0.000 description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 6
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
GRZNODNSNCXOHE-UHFFFAOYSA-N 2-chloro-1-oxidopyridin-1-ium;hydron;chloride Chemical compound Cl.[O-][N+]1=CC=CC=C1Cl GRZNODNSNCXOHE-UHFFFAOYSA-N 0.000 description 6
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-WFGJKAKNSA-N DMSO-d6 Substances [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
102000008946 Fibrinogen Human genes 0.000 description 6
108010049003 Fibrinogen Proteins 0.000 description 6
239000011324 bead Substances 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
238000005810 carbonylation reaction Methods 0.000 description 6
150000001735 carboxylic acids Chemical class 0.000 description 6
238000009833 condensation Methods 0.000 description 6
230000005494 condensation Effects 0.000 description 6
238000005859 coupling reaction Methods 0.000 description 6
125000004093 cyano group Chemical group *C#N 0.000 description 6
238000007257 deesterification reaction Methods 0.000 description 6
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229940012952 fibrinogen Drugs 0.000 description 6
150000003278 haem Chemical class 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
229910052740 iodine Inorganic materials 0.000 description 6
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 6
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239000006188 syrup Substances 0.000 description 6
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DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 5
238000012360 testing method Methods 0.000 description 5
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YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 4
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125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 4
LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 4
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229960000549 4-dimethylaminophenol Drugs 0.000 description 4
AVVKOSQEAVBDMJ-UHFFFAOYSA-N 5-(pyridin-2-ylamino)pentanoic acid Chemical compound OC(=O)CCCCNC1=CC=CC=N1 AVVKOSQEAVBDMJ-UHFFFAOYSA-N 0.000 description 4
108091003079 Bovine Serum Albumin Proteins 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
FVIGODVHAVLZOO-UHFFFAOYSA-N Dixanthogen Chemical compound CCOC(=S)SSC(=S)OCC FVIGODVHAVLZOO-UHFFFAOYSA-N 0.000 description 4
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
229910004373 HOAc Inorganic materials 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
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238000010521 absorption reaction Methods 0.000 description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
230000008878 coupling Effects 0.000 description 4
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229920001277 pectin Polymers 0.000 description 1
239000008188 pellet Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
238000005897 peptide coupling reaction Methods 0.000 description 1
239000000816 peptidomimetic Substances 0.000 description 1
239000002304 perfume Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
150000003904 phospholipids Chemical class 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
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
229920006289 polycarbonate film Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
235000015277 pork Nutrition 0.000 description 1
239000013641 positive control Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
DRTZAIDVOGUYSP-UHFFFAOYSA-N pyridin-1-ium;chloride;hydrochloride Chemical compound Cl.Cl.C1=CC=NC=C1 DRTZAIDVOGUYSP-UHFFFAOYSA-N 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000004366 reverse phase liquid chromatography Methods 0.000 description 1
102220240796 rs553605556 Human genes 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
238000013391 scatchard analysis Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000004400 serine Nutrition 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
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230000015590 smooth muscle cell migration Effects 0.000 description 1
239000003998 snake venom Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 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
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
IHQKEDIOMGYHEB-UHFFFAOYSA-M sodium dimethylarsinate Chemical compound [Na+].C[As](C)([O-])=O IHQKEDIOMGYHEB-UHFFFAOYSA-M 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
125000006850 spacer group Chemical group 0.000 description 1
230000009870 specific binding Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
OGBMKVWORPGQRR-UMXFMPSGSA-N teriparatide Chemical compound C([C@H](NC(=O)[C@H](CCSC)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@@H](N)CO)C(C)C)[C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)C1=CNC=N1 OGBMKVWORPGQRR-UMXFMPSGSA-N 0.000 description 1
LYDRKKWPKKEMNZ-UHFFFAOYSA-N tert-butyl benzoate Chemical compound CC(C)(C)OC(=O)C1=CC=CC=C1 LYDRKKWPKKEMNZ-UHFFFAOYSA-N 0.000 description 1
QYJVBVKFXDHFPQ-UHFFFAOYSA-N tert-butyl n-(2-aminoethyl)-n-methylcarbamate Chemical compound NCCN(C)C(=O)OC(C)(C)C QYJVBVKFXDHFPQ-UHFFFAOYSA-N 0.000 description 1
BDUZNKOFYSWAOZ-UHFFFAOYSA-N tert-butyl n-[2-(4-hydroxyphenyl)-2-oxoethyl]-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)CC(=O)C1=CC=C(O)C=C1 BDUZNKOFYSWAOZ-UHFFFAOYSA-N 0.000 description 1
HEXGKBKMDDSFRI-UHFFFAOYSA-N tert-butyl n-methyl-n-[2-(pyridin-2-ylamino)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)N(C)CCNC1=CC=CC=N1 HEXGKBKMDDSFRI-UHFFFAOYSA-N 0.000 description 1
CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-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
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
229960002180 tetracycline Drugs 0.000 description 1
229930101283 tetracycline Natural products 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
150000003522 tetracyclines Chemical class 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
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
NYERMPLPURRVGM-UHFFFAOYSA-N thiazepine Chemical compound S1C=CC=CC=N1 NYERMPLPURRVGM-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
238000004448 titration Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic 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
238000012546 transfer Methods 0.000 description 1
108091007466 transmembrane glycoproteins Proteins 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
125000004360 trifluorophenyl group Chemical group 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
210000001364 upper extremity Anatomy 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
210000004509 vascular smooth muscle cell Anatomy 0.000 description 1
238000005303 weighing Methods 0.000 description 1
GSQBIOQCECCMOQ-UHFFFAOYSA-N β-alanine ethyl ester Chemical compound CCOC(=O)CCN GSQBIOQCECCMOQ-UHFFFAOYSA-N 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- C07D405/02—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 two hetero rings
- C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Physical Education & Sports Medicine (AREA)
Rheumatology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Orthopedic Medicine & Surgery (AREA)
Vascular Medicine (AREA)
Pain & Pain Management (AREA)
Hematology (AREA)
Diabetes (AREA)
Urology & Nephrology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyridine Compounds (AREA)

JP9524453A 1995-12-29 1996-12-20 ビトロネクチン受容体拮抗物質 Pending JP2000502704A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US936795P	1995-12-29	1995-12-29
US60/009,367		1995-12-29
PCT/US1996/020327 WO1997024124A1 (en)	1995-12-29	1996-12-20	Vitronectin receptor antagonists

Publications (1)

Publication Number	Publication Date
JP2000502704A true JP2000502704A (ja)	2000-03-07

Family

ID=21737218

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP9524453A Pending JP2000502704A (ja)	1995-12-29	1996-12-20	ビトロネクチン受容体拮抗物質

Country Status (14)

Country	Link
US (1)	US6159964A (2)
EP (1)	EP0906103A1 (2)
JP (1)	JP2000502704A (2)
KR (1)	KR19990076877A (2)
CN (1)	CN1209063A (2)
AU (1)	AU1295597A (2)
BR (1)	BR9612381A (2)
CZ (1)	CZ203898A3 (2)
IL (1)	IL125030A0 (2)
NO (1)	NO983001L (2)
PL (1)	PL327626A1 (2)
TR (1)	TR199801254T2 (2)
WO (1)	WO1997024124A1 (2)
ZA (1)	ZA9610854B (2)

Families Citing this family (68)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1996006087A1 (en) *	1994-08-22	1996-02-29	Smithkline Beecham Corporation	Bicyclic compounds
EP0895475A4 (en) *	1995-12-29	2000-08-23	Smithkline Beecham Corp	VITRONECTIN RECEPTOR ANTAGONISTS
JP2000508319A (ja) *	1996-04-10	2000-07-04	メルクエンドカンパニーインコーポレーテッド	αｖβ３拮抗薬
US20030125317A1 (en)	1996-10-02	2003-07-03	Smithkline Beecham Corporation	Vitronectin receptor antagonists
DE19653647A1 (de) *	1996-12-20	1998-06-25	Hoechst Ag	Vitronectin - Rezeptorantagonisten, deren Herstellung sowie deren Verwendung
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- 1996-12-20 BR BR9612381A patent/BR9612381A/pt unknown
- 1996-12-20 JP JP9524453A patent/JP2000502704A/ja active Pending
- 1996-12-20 US US09/091,937 patent/US6159964A/en not_active Expired - Fee Related
- 1996-12-20 TR TR1998/01254T patent/TR199801254T2/xx unknown
- 1996-12-20 PL PL96327626A patent/PL327626A1/xx unknown
- 1996-12-20 EP EP96943818A patent/EP0906103A1/en not_active Withdrawn
- 1996-12-20 IL IL12503096A patent/IL125030A0/xx unknown
- 1996-12-20 KR KR1019980705004A patent/KR19990076877A/ko not_active Withdrawn
- 1996-12-20 CZ CZ982038A patent/CZ203898A3/cs unknown
- 1996-12-20 CN CN96180114A patent/CN1209063A/zh active Pending
- 1996-12-20 AU AU12955/97A patent/AU1295597A/en not_active Abandoned
- 1996-12-23 ZA ZA9610854A patent/ZA9610854B/xx unknown
1998
- 1998-06-26 NO NO983001A patent/NO983001L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
ZA9610854B (en)	1998-04-02
AU1295597A (en)	1997-07-28
BR9612381A (pt)	1999-07-13
WO1997024124A1 (en)	1997-07-10
NO983001D0 (no)	1998-06-26
TR199801254T2 (xx)	1998-10-21
EP0906103A1 (en)	1999-04-07
CZ203898A3 (cs)	1999-03-17
IL125030A0 (en)	1999-01-26
US6159964A (en)	2000-12-12
PL327626A1 (en)	1998-12-21
KR19990076877A (ko)	1999-10-25
NO983001L (no)	1998-08-26
EP0906103A4 (2)	1999-04-07
CN1209063A (zh)	1999-02-24

Publication	Publication Date	Title
JP2000502704A (ja)	2000-03-07	ビトロネクチン受容体拮抗物質
JP2000502708A (ja)	2000-03-07	ビトロネクチン受容体拮抗物質
DE69332860T2 (de)	2004-03-11	Bicyklische fibrinogen antagoniste
US6239138B1 (en)	2001-05-29	Vitronectin receptor antagonist
JP2000502354A (ja)	2000-02-29	ビトロネクチン受容体アンタゴニスト
JP3960482B2 (ja)	2007-08-15	インテグリン受容体アンタゴニスト
JPH10504807A (ja)	1998-05-12	ビトロネクチン受容体拮抗剤
HUT76344A (en)	1997-08-28	Vitronectin receptor antagonists
JP2001511452A (ja)	2001-08-14	インテグリン受容体アンタゴニスト
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JP2001514253A (ja)	2001-09-11	インテグリンレセプターアンタゴニスト
US6495560B1 (en)	2002-12-17	Vitronectin receptor antagonist
US20010034445A1 (en)	2001-10-25	Vitronectin receptor antagonists
HUP0103090A2 (hu)	2002-01-28	Vitronektin receptor antagonista oxazolszármazékok, eljárás az előállításukra, a vegyületeket tartalmazó gyógyászati készítmények és alkalmazásuk
US6403578B1 (en)	2002-06-11	Bicyclic fibrinogen antagonists
KR100459621B1 (ko)	2005-09-02	인테그린수용체길항제
MXPA98005254A (en)	1999-02-24	Vitronect receptor antagonists
CA2241755A1 (en)	1997-07-10	Vitronectin receptor antagonists
CZ2000979A3 (cs)	2000-11-15	Antagonista vitronektinového receptoru
HK1019594B (en)	2003-12-24	Integrin receptor antagonists