UA71586C2 - A vitronectin receptor antagonist - Google Patents

A vitronectin receptor antagonist Download PDF

Info

Publication number: UA71586C2
Authority: UA; Ukraine
Prior art keywords: compound; formula; cells; preparation; treatment
Prior art date: 1998-12-04

Application number

UA2001063754A

Other languages

English (en)

Ukrainian (uk)

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.)

1998-12-04

Filing date

1999-03-12

Publication date

2004-12-15

1999-03-12 Application filed by Smithkline Beecham Corp filed Critical Smithkline Beecham Corp

2004-12-15 Publication of UA71586C2 publication Critical patent/UA71586C2/uk

Links

102100022337 Integrin alpha-V Human genes 0.000 title abstract description 20
108010048673 Vitronectin Receptors Proteins 0.000 title abstract description 20
239000002464 receptor antagonist Substances 0.000 title abstract 2
229940044551 receptor antagonist Drugs 0.000 title abstract 2
150000001875 compounds Chemical class 0.000 claims abstract description 129
238000011282 treatment Methods 0.000 claims abstract description 28
208000001132 Osteoporosis Diseases 0.000 claims abstract description 11
150000003839 salts Chemical class 0.000 claims abstract description 10
238000000034 method Methods 0.000 claims description 41
238000002360 preparation method Methods 0.000 claims description 25
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
201000010099 disease Diseases 0.000 claims description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
206010028980 Neoplasm Diseases 0.000 claims description 16
239000002246 antineoplastic agent Substances 0.000 claims description 15
239000005557 antagonist Substances 0.000 claims description 14
210000000988 bone and bone Anatomy 0.000 claims description 13
239000003795 chemical substances by application Substances 0.000 claims description 9
239000008194 pharmaceutical composition Substances 0.000 claims description 9
230000002401 inhibitory effect Effects 0.000 claims description 8
208000037803 restenosis Diseases 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 7
230000003993 interaction Effects 0.000 claims description 7
201000001320 Atherosclerosis Diseases 0.000 claims description 6
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 6
229960004316 cisplatin Drugs 0.000 claims description 6
229940126601 medicinal product Drugs 0.000 claims description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
230000009471 action Effects 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
239000003112 inhibitor Substances 0.000 claims description 5
230000004614 tumor growth Effects 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 4
UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical group C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 claims description 4
229960000303 topotecan Drugs 0.000 claims description 4
206010027476 Metastases Diseases 0.000 claims description 3
230000033115 angiogenesis Effects 0.000 claims description 3
206010061218 Inflammation Diseases 0.000 claims description 2
230000004054 inflammatory process Effects 0.000 claims description 2
230000009401 metastasis Effects 0.000 claims description 2
238000010931 ester hydrolysis Methods 0.000 claims 1
WPDZACQODUHYCH-UHFFFAOYSA-N propan-2-yloxycarbonyliminocarbamic acid Chemical compound CC(C)OC(=O)N=NC(O)=O WPDZACQODUHYCH-UHFFFAOYSA-N 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
210000004027 cell Anatomy 0.000 description 74
239000000203 mixture Substances 0.000 description 49
239000000243 solution Substances 0.000 description 42
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
210000002997 osteoclast Anatomy 0.000 description 35
239000002609 medium Substances 0.000 description 28
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
241000282414 Homo sapiens Species 0.000 description 20
239000000872 buffer Substances 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
-1 thrombopondin Proteins 0.000 description 18
229910001868 water Inorganic materials 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
238000004458 analytical method Methods 0.000 description 16
239000003921 oil Substances 0.000 description 16
235000019198 oils Nutrition 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000007788 liquid Substances 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
235000002639 sodium chloride Nutrition 0.000 description 14
239000007787 solid Substances 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
229960000583 acetic acid Drugs 0.000 description 12
239000011324 bead Substances 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
238000005481 NMR spectroscopy Methods 0.000 description 11
241000700159 Rattus Species 0.000 description 11
238000005119 centrifugation Methods 0.000 description 11
235000019439 ethyl acetate Nutrition 0.000 description 11
239000010410 layer Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
238000003756 stirring Methods 0.000 description 10
239000000725 suspension Substances 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
208000006386 Bone Resorption Diseases 0.000 description 9
108091003079 Bovine Serum Albumin Proteins 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
230000024279 bone resorption Effects 0.000 description 9
229940098773 bovine serum albumin Drugs 0.000 description 9
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
239000000126 substance Substances 0.000 description 9
239000012737 fresh medium Substances 0.000 description 8
238000011534 incubation Methods 0.000 description 8
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
210000001519 tissue Anatomy 0.000 description 8
238000005406 washing Methods 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
239000012300 argon atmosphere Substances 0.000 description 7
230000027455 binding Effects 0.000 description 7
210000004204 blood vessel Anatomy 0.000 description 7
239000000284 extract Substances 0.000 description 7
102000005962 receptors Human genes 0.000 description 7
108020003175 receptors Proteins 0.000 description 7
230000002829 reductive effect Effects 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
108010031318 Vitronectin Proteins 0.000 description 6
102100035140 Vitronectin Human genes 0.000 description 6
239000002253 acid Substances 0.000 description 6
238000003556 assay Methods 0.000 description 6
239000011575 calcium Substances 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
239000006285 cell suspension Substances 0.000 description 6
238000010494 dissociation reaction Methods 0.000 description 6
230000005593 dissociations Effects 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
230000012010 growth Effects 0.000 description 6
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
238000001819 mass spectrum Methods 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
210000005087 mononuclear cell Anatomy 0.000 description 6
238000007911 parenteral administration Methods 0.000 description 6
239000000843 powder Substances 0.000 description 6
230000008569 process Effects 0.000 description 6
238000003860 storage Methods 0.000 description 6
WEMUNMQFXOILNO-UHFFFAOYSA-N 2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethanol Chemical compound C1CCNC2=NC(CCO)=CC=C21 WEMUNMQFXOILNO-UHFFFAOYSA-N 0.000 description 5
108010012088 Fibrinogen Receptors Proteins 0.000 description 5
208000002966 Giant Cell Tumor of Bone Diseases 0.000 description 5
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
239000008121 dextrose Substances 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
238000002347 injection Methods 0.000 description 5
239000007924 injection Substances 0.000 description 5
239000003446 ligand Substances 0.000 description 5
238000002156 mixing Methods 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
229910052697 platinum Inorganic materials 0.000 description 5
108090000765 processed proteins & peptides Proteins 0.000 description 5
108090000623 proteins and genes Proteins 0.000 description 5
230000009467 reduction Effects 0.000 description 5
239000007790 solid phase Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
206010065687 Bone loss Diseases 0.000 description 4
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
108010010803 Gelatin Proteins 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
206010029113 Neovascularisation Diseases 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
102000007591 Tartrate-Resistant Acid Phosphatase Human genes 0.000 description 4
108010032050 Tartrate-Resistant Acid Phosphatase Proteins 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000002585 base Substances 0.000 description 4
201000011510 cancer Diseases 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
239000000969 carrier Substances 0.000 description 4
230000021164 cell adhesion Effects 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
230000002860 competitive effect Effects 0.000 description 4
150000008508 dibenzocycloheptenes Chemical class 0.000 description 4
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 4
239000002552 dosage form Substances 0.000 description 4
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000012634 fragment Substances 0.000 description 4
239000008273 gelatin Substances 0.000 description 4
229920000159 gelatin Polymers 0.000 description 4
235000019322 gelatine Nutrition 0.000 description 4
235000011852 gelatine desserts Nutrition 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
235000012907 honey Nutrition 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
238000001990 intravenous administration Methods 0.000 description 4
239000002502 liposome Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
230000009871 nonspecific binding Effects 0.000 description 4
230000007170 pathology Effects 0.000 description 4
239000002953 phosphate buffered saline Substances 0.000 description 4
VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 4
102000004169 proteins and genes Human genes 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
238000002560 therapeutic procedure Methods 0.000 description 4
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 4
239000003981 vehicle Substances 0.000 description 4
CHADEQDQBURGHL-UHFFFAOYSA-N (6'-acetyloxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl) acetate Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(OC(C)=O)C=C1OC1=CC(OC(=O)C)=CC=C21 CHADEQDQBURGHL-UHFFFAOYSA-N 0.000 description 3
PORCOIDPPYVUBC-UHFFFAOYSA-N 2-(2-benzyl-4-methoxyphenyl)acetic acid Chemical compound COC1=CC=C(CC(O)=O)C(CC=2C=CC=CC=2)=C1 PORCOIDPPYVUBC-UHFFFAOYSA-N 0.000 description 3
LVFFZQQWIZURIO-UHFFFAOYSA-N 2-phenylbutanedioic acid Chemical compound OC(=O)CC(C(O)=O)C1=CC=CC=C1 LVFFZQQWIZURIO-UHFFFAOYSA-N 0.000 description 3
241000283707 Capra Species 0.000 description 3
208000024172 Cardiovascular disease Diseases 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
239000000654 additive Substances 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
150000001540 azides Chemical class 0.000 description 3
230000008901 benefit Effects 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
210000002805 bone matrix Anatomy 0.000 description 3
244000309466 calf Species 0.000 description 3
VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical class C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
230000009137 competitive binding Effects 0.000 description 3
238000011161 development Methods 0.000 description 3
230000018109 developmental process Effects 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
238000010828 elution Methods 0.000 description 3
208000030533 eye disease Diseases 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000007903 gelatin capsule Substances 0.000 description 3
238000007429 general method Methods 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
230000003100 immobilizing effect Effects 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
238000001802 infusion Methods 0.000 description 3
102000006495 integrins Human genes 0.000 description 3
108010044426 integrins Proteins 0.000 description 3
206010023332 keratitis Diseases 0.000 description 3
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000012528 membrane Substances 0.000 description 3
230000014399 negative regulation of angiogenesis Effects 0.000 description 3
HEGSGKPQLMEBJL-RKQHYHRCSA-N octyl beta-D-glucopyranoside Chemical compound CCCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HEGSGKPQLMEBJL-RKQHYHRCSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
239000004033 plastic Substances 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
230000002335 preservative effect Effects 0.000 description 3
230000002265 prevention Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
210000002966 serum Anatomy 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
239000006228 supernatant Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
231100000331 toxic Toxicity 0.000 description 3
230000002588 toxic effect Effects 0.000 description 3
TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 2
PIRRWUMTIBFCCW-UHFFFAOYSA-N 1-(2-fluoro-4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(C)=O)C(F)=C1 PIRRWUMTIBFCCW-UHFFFAOYSA-N 0.000 description 2
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
XFEFRJSZJKFVKG-UHFFFAOYSA-N 2-(2-benzoyl-4-methoxyphenyl)acetic acid Chemical compound COC1=CC=C(CC(O)=O)C(C(=O)C=2C=CC=CC=2)=C1 XFEFRJSZJKFVKG-UHFFFAOYSA-N 0.000 description 2
IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
244000215068 Acacia senegal Species 0.000 description 2
208000010392 Bone Fractures Diseases 0.000 description 2
241000283690 Bos taurus Species 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
108010022452 Collagen Type I Proteins 0.000 description 2
102000012422 Collagen Type I Human genes 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
238000002965 ELISA Methods 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
229920000084 Gum arabic Polymers 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
201000002980 Hyperparathyroidism Diseases 0.000 description 2
239000003810 Jones reagent Substances 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
229930195725 Mannitol Natural products 0.000 description 2
206010027452 Metastases to bone Diseases 0.000 description 2
208000010191 Osteitis Deformans Diseases 0.000 description 2
108010081689 Osteopontin Proteins 0.000 description 2
102000004264 Osteopontin Human genes 0.000 description 2
208000027868 Paget disease Diseases 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
206010052428 Wound Diseases 0.000 description 2
208000027418 Wounds and injury Diseases 0.000 description 2
239000000205 acacia gum Substances 0.000 description 2
235000010489 acacia gum Nutrition 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
238000005575 aldol reaction Methods 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
210000004381 amniotic fluid Anatomy 0.000 description 2
230000002491 angiogenic effect Effects 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
230000036770 blood supply Effects 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
PASHVRUKOFIRIK-UHFFFAOYSA-L calcium sulfate dihydrate Chemical compound O.O.[Ca+2].[O-]S([O-])(=O)=O PASHVRUKOFIRIK-UHFFFAOYSA-L 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000004113 cell culture Methods 0.000 description 2
239000012501 chromatography medium Substances 0.000 description 2
229940096422 collagen type i Drugs 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000004624 confocal microscopy Methods 0.000 description 2
239000010949 copper Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
230000007812 deficiency Effects 0.000 description 2
239000008367 deionised water Substances 0.000 description 2
229910021641 deionized water Inorganic materials 0.000 description 2
210000004268 dentin Anatomy 0.000 description 2
238000000502 dialysis Methods 0.000 description 2
PJQCANLCUDUPRF-UHFFFAOYSA-N dibenzocycloheptene Chemical compound C1CC2=CC=CC=C2CC2=CC=CC=C12 PJQCANLCUDUPRF-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
238000011049 filling Methods 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000003163 gonadal steroid hormone Substances 0.000 description 2
238000000227 grinding Methods 0.000 description 2
210000005119 human aortic smooth muscle cell Anatomy 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
239000005457 ice water Substances 0.000 description 2
230000002757 inflammatory effect Effects 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
238000010253 intravenous injection Methods 0.000 description 2
239000008101 lactose Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
208000027202 mammary Paget disease Diseases 0.000 description 2
239000000594 mannitol Substances 0.000 description 2
235000010355 mannitol Nutrition 0.000 description 2
239000003550 marker Substances 0.000 description 2
230000001404 mediated effect Effects 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
230000005012 migration Effects 0.000 description 2
238000013508 migration Methods 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
230000000010 osteolytic effect Effects 0.000 description 2
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
230000000849 parathyroid Effects 0.000 description 2
231100000915 pathological change Toxicity 0.000 description 2
230000036285 pathological change Effects 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000012071 phase Substances 0.000 description 2
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 2
150000003904 phospholipids Chemical class 0.000 description 2
210000002826 placenta Anatomy 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
229920000137 polyphosphoric acid Polymers 0.000 description 2
239000000651 prodrug Substances 0.000 description 2
229940002612 prodrug Drugs 0.000 description 2
LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical group 0.000 description 2
230000002285 radioactive effect Effects 0.000 description 2
238000011552 rat model Methods 0.000 description 2
238000011084 recovery Methods 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
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 2
230000001225 therapeutic effect Effects 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 2
125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical group [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
XLBBKEHLEPNMMF-SSUNCQRMSA-N 129038-42-2 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CS)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(N)=O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)[C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CS)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CS)NC(=O)[C@H](CS)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CS)NC(=O)[C@@H](N)CCC(O)=O)C1=CC=CC=C1 XLBBKEHLEPNMMF-SSUNCQRMSA-N 0.000 description 1
BECNVKMMZXDHJE-UHFFFAOYSA-N 2-(2-benzoyl-4-methoxyphenyl)acetic acid 2-(2-benzyl-4-methoxyphenyl)acetic acid Chemical compound C(C1=CC=CC=C1)(=O)C1=C(C=CC(=C1)OC)CC(=O)O.C(C1=CC=CC=C1)C1=C(C=CC(=C1)OC)CC(=O)O BECNVKMMZXDHJE-UHFFFAOYSA-N 0.000 description 1
FSWRUYCICUXURT-UHFFFAOYSA-N 2-methyl-1,8-naphthyridine Chemical compound C1=CC=NC2=NC(C)=CC=C21 FSWRUYCICUXURT-UHFFFAOYSA-N 0.000 description 1
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
NTSRMGPINJLVFK-UHFFFAOYSA-N 3-(3-methoxyphenyl)-1h-indene Chemical compound COC1=CC=CC(C=2C3=CC=CC=C3CC=2)=C1 NTSRMGPINJLVFK-UHFFFAOYSA-N 0.000 description 1
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
MCNQUWLLXZZZAC-UHFFFAOYSA-N 4-cyano-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-n-piperidin-1-ylpyrazole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=C(C#N)C(C(=O)NN2CCCCC2)=NN1C1=CC=C(Cl)C=C1Cl MCNQUWLLXZZZAC-UHFFFAOYSA-N 0.000 description 1
AXSNHYKONIHNHH-UHFFFAOYSA-N 6-methoxy-1-phenyl-1h-indene Chemical compound C12=CC(OC)=CC=C2C=CC1C1=CC=CC=C1 AXSNHYKONIHNHH-UHFFFAOYSA-N 0.000 description 1
FUXVKZWTXQUGMW-FQEVSTJZSA-N 9-Aminocamptothecin Chemical compound C1=CC(N)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 FUXVKZWTXQUGMW-FQEVSTJZSA-N 0.000 description 1
206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
OGSPWJRAVKPPFI-UHFFFAOYSA-N Alendronic Acid Chemical compound NCCCC(O)(P(O)(O)=O)P(O)(O)=O OGSPWJRAVKPPFI-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
208000023275 Autoimmune disease Diseases 0.000 description 1
229940122361 Bisphosphonate Drugs 0.000 description 1
208000020084 Bone disease Diseases 0.000 description 1
229940078581 Bone resorption inhibitor Drugs 0.000 description 1
241000283725 Bos Species 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
102000055006 Calcitonin Human genes 0.000 description 1
108060001064 Calcitonin Proteins 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
108010035532 Collagen Proteins 0.000 description 1
102000008186 Collagen Human genes 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
XUIIKFGFIJCVMT-GFCCVEGCSA-N D-thyroxine Chemical compound IC1=CC(C[C@@H](N)C(O)=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-GFCCVEGCSA-N 0.000 description 1
201000004624 Dermatitis Diseases 0.000 description 1
206010012442 Dermatitis contact Diseases 0.000 description 1
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 1
206010012689 Diabetic retinopathy Diseases 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
101000761020 Dinoponera quadriceps Poneritoxin Proteins 0.000 description 1
101100294331 Drosophila melanogaster nod gene Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
206010063560 Excessive granulation tissue Diseases 0.000 description 1
108010073385 Fibrin Proteins 0.000 description 1
102000009123 Fibrin Human genes 0.000 description 1
BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 1
102000008946 Fibrinogen Human genes 0.000 description 1
108010049003 Fibrinogen Proteins 0.000 description 1
108010067306 Fibronectins Proteins 0.000 description 1
102000016359 Fibronectins Human genes 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
206010017076 Fracture Diseases 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
208000010412 Glaucoma Diseases 0.000 description 1
SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 1
208000009329 Graft vs Host Disease Diseases 0.000 description 1
201000002563 Histoplasmosis Diseases 0.000 description 1
241000282412 Homo Species 0.000 description 1
101000613820 Homo sapiens Osteopontin Proteins 0.000 description 1
101000703512 Homo sapiens Sphingosine-1-phosphate phosphatase 1 Proteins 0.000 description 1
101000803709 Homo sapiens Vitronectin Proteins 0.000 description 1
208000037147 Hypercalcaemia Diseases 0.000 description 1
206010020584 Hypercalcaemia of malignancy Diseases 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
208000022559 Inflammatory bowel disease Diseases 0.000 description 1
108010028750 Integrin-Binding Sialoprotein Proteins 0.000 description 1
102000016921 Integrin-Binding Sialoprotein Human genes 0.000 description 1
102000007547 Laminin Human genes 0.000 description 1
108010085895 Laminin Proteins 0.000 description 1
102000004856 Lectins Human genes 0.000 description 1
108090001090 Lectins Proteins 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
LOJFGJZQOKTUBR-XAQOOIOESA-N NC(N)=NCCC[C@@H](C(O)=O)NC(=O)CNC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CCC(O)=O)C)CC1=CN=CN1 Chemical compound NC(N)=NCCC[C@@H](C(O)=O)NC(=O)CNC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CCC(O)=O)C)CC1=CN=CN1 LOJFGJZQOKTUBR-XAQOOIOESA-N 0.000 description 1
208000034827 Neointima Diseases 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
102000004067 Osteocalcin Human genes 0.000 description 1
108090000573 Osteocalcin Proteins 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
241001111421 Pannus Species 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
108010039918 Polylysine Proteins 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
101001121466 Rattus norvegicus Osteopontin Proteins 0.000 description 1
101000703459 Rattus norvegicus Sphingosine-1-phosphate phosphatase 1 Proteins 0.000 description 1
208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
208000004756 Respiratory Insufficiency Diseases 0.000 description 1
206010038933 Retinopathy of prematurity Diseases 0.000 description 1
229920002684 Sepharose Polymers 0.000 description 1
206010040070 Septic Shock Diseases 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
208000001435 Thromboembolism Diseases 0.000 description 1
102100023935 Transmembrane glycoprotein NMB Human genes 0.000 description 1
206010052779 Transplant rejections Diseases 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
239000008351 acetate buffer Substances 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
102000019997 adhesion receptor Human genes 0.000 description 1
108010013985 adhesion receptor Proteins 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
206010064930 age-related macular degeneration Diseases 0.000 description 1
229940062527 alendronate Drugs 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
230000007815 allergy Effects 0.000 description 1
QNXSIUBBGPHDDE-UHFFFAOYSA-N alpha-indanone Natural products C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
239000003708 ampul Substances 0.000 description 1
239000003263 anabolic agent Substances 0.000 description 1
229940124325 anabolic agent Drugs 0.000 description 1
238000012435 analytical chromatography Methods 0.000 description 1
239000004037 angiogenesis inhibitor Substances 0.000 description 1
230000001772 anti-angiogenic effect Effects 0.000 description 1
229940046836 anti-estrogen Drugs 0.000 description 1
230000001833 anti-estrogenic effect Effects 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
239000002257 antimetastatic agent Substances 0.000 description 1
230000006907 apoptotic process Effects 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
150000008038 benzoazepines Chemical class 0.000 description 1
RROBIDXNTUAHFW-UHFFFAOYSA-N benzotriazol-1-yloxy-tris(dimethylamino)phosphanium Chemical compound C1=CC=C2N(O[P+](N(C)C)(N(C)C)N(C)C)N=NC2=C1 RROBIDXNTUAHFW-UHFFFAOYSA-N 0.000 description 1
239000012148 binding buffer Substances 0.000 description 1
238000004166 bioassay Methods 0.000 description 1
150000004663 bisphosphonates Chemical class 0.000 description 1
230000000740 bleeding effect Effects 0.000 description 1
238000010241 blood sampling Methods 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000002617 bone density conservation agent Substances 0.000 description 1
230000010072 bone remodeling Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
230000000125 calcaemic effect Effects 0.000 description 1
BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)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]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 description 1
229960004015 calcitonin Drugs 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
230000024245 cell differentiation Effects 0.000 description 1
230000012292 cell migration Effects 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
239000007979 citrate buffer Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000010367 cloning Methods 0.000 description 1
239000003245 coal Substances 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
229920001436 collagen Polymers 0.000 description 1
108010049937 collagen type I trimeric cross-linked peptide Proteins 0.000 description 1
208000010247 contact dermatitis Diseases 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
210000004087 cornea Anatomy 0.000 description 1
238000007887 coronary angioplasty Methods 0.000 description 1
230000001054 cortical effect Effects 0.000 description 1
150000003997 cyclic ketones Chemical class 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
238000006392 deoxygenation reaction Methods 0.000 description 1
230000001066 destructive effect Effects 0.000 description 1
150000001987 diarylethers Chemical class 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000012377 drug delivery Methods 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
108010025752 echistatin Proteins 0.000 description 1
238000000132 electrospray ionisation Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000013504 emergency use authorization Methods 0.000 description 1
210000002889 endothelial cell Anatomy 0.000 description 1
239000000328 estrogen antagonist Substances 0.000 description 1
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
201000010934 exostosis Diseases 0.000 description 1
238000000605 extraction Methods 0.000 description 1
229950003499 fibrin Drugs 0.000 description 1
229940012952 fibrinogen Drugs 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
230000006870 function Effects 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
239000002223 garnet Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
229940074045 glyceryl distearate Drugs 0.000 description 1
229940075507 glyceryl monostearate Drugs 0.000 description 1
208000024908 graft versus host disease Diseases 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
210000001126 granulation tissue Anatomy 0.000 description 1
230000035876 healing Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000002439 hemostatic effect Effects 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
238000002657 hormone replacement therapy Methods 0.000 description 1
208000008750 humoral hypercalcemia of malignancy Diseases 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
230000000148 hypercalcaemia Effects 0.000 description 1
208000030915 hypercalcemia disease Diseases 0.000 description 1
201000010930 hyperostosis Diseases 0.000 description 1
238000003018 immunoassay Methods 0.000 description 1
238000010166 immunofluorescence Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
238000007373 indentation Methods 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 description 1
229960004768 irinotecan Drugs 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
210000003292 kidney cell Anatomy 0.000 description 1
239000002523 lectin Substances 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
239000008176 lyophilized powder Substances 0.000 description 1
239000006166 lysate Substances 0.000 description 1
208000002780 macular degeneration Diseases 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
208000030159 metabolic disease Diseases 0.000 description 1
229940071648 metered dose inhaler Drugs 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
238000000386 microscopy Methods 0.000 description 1
210000004088 microvessel Anatomy 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
230000000921 morphogenic effect Effects 0.000 description 1
229940126619 mouse monoclonal antibody Drugs 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000004651 near-field scanning optical microscopy Methods 0.000 description 1
239000006199 nebulizer Substances 0.000 description 1
230000010807 negative regulation of binding Effects 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
201000003142 neovascular glaucoma Diseases 0.000 description 1
230000037311 normal skin Effects 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
RQFLGKYCYMMRMC-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O RQFLGKYCYMMRMC-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
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
229950008017 ormaplatin Drugs 0.000 description 1
239000012285 osmium tetroxide Substances 0.000 description 1
229910000489 osmium tetroxide Inorganic materials 0.000 description 1
230000011164 ossification Effects 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
230000001599 osteoclastic effect Effects 0.000 description 1
208000005368 osteomalacia Diseases 0.000 description 1
208000002865 osteopetrosis Diseases 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 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
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
238000002264 polyacrylamide gel electrophoresis Methods 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
229920000656 polylysine Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
102000040430 polynucleotide Human genes 0.000 description 1
108091033319 polynucleotide Proteins 0.000 description 1
239000002157 polynucleotide Substances 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
239000011148 porous material Substances 0.000 description 1
239000013641 positive control Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
238000004321 preservation Methods 0.000 description 1
238000003825 pressing Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000000310 rehydration solution Substances 0.000 description 1
201000004193 respiratory failure Diseases 0.000 description 1
230000004044 response Effects 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000007790 scraping Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000036303 septic shock Effects 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
230000015590 smooth muscle cell migration Effects 0.000 description 1
210000000329 smooth muscle myocyte Anatomy 0.000 description 1
239000003998 snake venom Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 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
IHQKEDIOMGYHEB-UHFFFAOYSA-M sodium dimethylarsinate Chemical compound [Na+].C[As](C)([O-])=O IHQKEDIOMGYHEB-UHFFFAOYSA-M 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000001433 sodium tartrate Substances 0.000 description 1
229960002167 sodium tartrate Drugs 0.000 description 1
235000011004 sodium tartrates Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000002764 solid phase assay Methods 0.000 description 1
230000009870 specific binding Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000829 suppository Substances 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
238000010189 synthetic method Methods 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
CHWMFCCGEWQABK-UHFFFAOYSA-N tert-butyl 7-methyl-3,4-dihydro-2h-1,8-naphthyridine-1-carboxylate Chemical compound C1CCN(C(=O)OC(C)(C)C)C2=NC(C)=CC=C21 CHWMFCCGEWQABK-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
229940034208 thyroxine Drugs 0.000 description 1
XUIIKFGFIJCVMT-UHFFFAOYSA-N thyroxine-binding globulin Natural products IC1=CC(CC([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-UHFFFAOYSA-N 0.000 description 1
229950003937 tolonium Drugs 0.000 description 1
108091007466 transmembrane glycoproteins Proteins 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
238000001665 trituration Methods 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1
238000000825 ultraviolet detection Methods 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
230000002792 vascular Effects 0.000 description 1
210000004509 vascular smooth muscle cell Anatomy 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1
230000029663 wound healing Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
- A61K33/243—Platinum; Compounds thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological 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
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- 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
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic 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

Landscapes

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

UA2001063754A 1998-12-04 1999-03-12 A vitronectin receptor antagonist UA71586C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US11090398P	1998-12-04	1998-12-04
PCT/US1999/028662 WO2000033838A1 (en)	1998-12-04	1999-12-03	Vitronectin receptor antagonist

Publications (1)

Publication Number	Publication Date
UA71586C2 true UA71586C2 (en)	2004-12-15

Family

ID=22335565

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2001063754A UA71586C2 (en)	1998-12-04	1999-03-12	A vitronectin receptor antagonist

Country Status (39)

Country	Link
US (1)	US6495560B1 (da)
EP (1)	EP1146874B1 (da)
JP (1)	JP4481504B2 (da)
KR (1)	KR100620485B1 (da)
CN (1)	CN1147300C (da)
AP (1)	AP1534A (da)
AR (1)	AR035006A1 (da)
AT (1)	ATE277043T1 (da)
AU (1)	AU754408B2 (da)
BG (1)	BG65118B1 (da)
BR (1)	BR9915879A (da)
CA (1)	CA2353415A1 (da)
CO (1)	CO5150166A1 (da)
CZ (1)	CZ20011963A3 (da)
DE (1)	DE69920518T2 (da)
DK (1)	DK1146874T3 (da)
DZ (1)	DZ2954A1 (da)
EA (1)	EA003254B1 (da)
EG (1)	EG24025A (da)
ES (1)	ES2229798T3 (da)
HK (1)	HK1042037B (da)
HU (1)	HUP0104804A3 (da)
ID (1)	ID28811A (da)
IL (2)	IL143390A0 (da)
MA (1)	MA25265A1 (da)
NO (1)	NO318895B1 (da)
NZ (1)	NZ511876A (da)
OA (1)	OA11724A (da)
PE (1)	PE20001563A1 (da)
PL (1)	PL195973B1 (da)
PT (1)	PT1146874E (da)
SI (1)	SI1146874T1 (da)
SK (1)	SK7452001A3 (da)
TR (1)	TR200101654T2 (da)
TW (1)	TW482673B (da)
UA (1)	UA71586C2 (da)
UY (1)	UY25824A1 (da)
WO (1)	WO2000033838A1 (da)
ZA (1)	ZA200104398B (da)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
UY26780A1 (es) *	2000-06-15	2002-01-31	Pharmacia Corp	Cicloalquil avb3 antagonistas
JP2004513953A (ja) *	2000-10-24	2004-05-13	メルク　エンド　カムパニー　インコーポレーテッド	ジベンズオキサゼピンαＶインテグリン受容体アンタゴニスト
WO2002060438A1 (en)	2001-01-29	2002-08-08	3-Dimensional Pharmaceuticals, Inc.	Substituted indoles and their use as integrin antagonists
US6872730B2 (en)	2001-04-27	2005-03-29	3-Dimensional Pharmaceuticals, Inc.	Substituted benzofurans and benzothiophenes, methods of making and methods of use as integrin antagonists
US20040224986A1 (en)	2002-08-16	2004-11-11	Bart De Corte	Piperidinyl targeting compounds that selectively bind integrins
BR0316876A (pt)	2002-12-20	2005-10-25	Pharmacia Corp	Compostos de tiazol e composição farmacêutica compreendendo o mesmo
GB0319069D0 (en) *	2003-08-14	2003-09-17	Glaxo Group Ltd	Therapeutically useful compounds
TW200635902A (en) *	2004-12-21	2006-10-16	Smithkline Beecham Corp	Methods and formulations
BR112013000946B1 (pt)	2010-07-14	2020-09-08	Novartis Ag	Compostos heterocíclicos agonistas de receptor de ip, seus usos, composição e combinação farmacêuticas
AR089698A1 (es)	2012-01-13	2014-09-10	Novartis Ag	Compuestos heterociclicos antagonistas del receptor ip
ES2637719T3 (es)	2013-02-13	2017-10-16	Novartis Ag	Compuestos heterocíclicos agonistas del receptor IP
DK3929196T3 (da)	2013-09-24	2023-09-25	Fujifilm Corp	Farmaceutisk sammensætning af en nitrogenholdig forbindelse eller salt deraf, eller metalkompleks deraf

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2687154B1 (fr)	1992-02-07	1995-05-12	Rhone Poulenc Rorer Sa	Nouveau derive de l'isoindolinone, sa preparation et les compositions pharmaceutiques qui le contiennent.
SI0910563T1 (en) *	1995-06-29	2003-10-31	Smithkline Beecham Corporation	Integrin receptor antagonists
AU4109297A (en) *	1996-09-27	1998-04-17	Merkler, H.	Tank for liquids, particularly for chemically aggressive liquids
EP0946180A4 (en) *	1996-10-07	2003-07-23	Smithkline Beecham Corp	METHODS FOR STIMULATING BONE FORMATION
UY24949A1 (es)	1997-04-08	2001-04-30	Smithkline Beecham Corp	Compuestos calcilíticos

1999
- 1999-03-12 UA UA2001063754A patent/UA71586C2/uk unknown
- 1999-11-29 TW TW088120752A patent/TW482673B/zh not_active IP Right Cessation
- 1999-11-29 UY UY25824A patent/UY25824A1/es unknown
- 1999-11-30 CO CO99075061A patent/CO5150166A1/es unknown
- 1999-11-30 PE PE1999001197A patent/PE20001563A1/es not_active Application Discontinuation
- 1999-12-01 DZ DZ990254A patent/DZ2954A1/xx active
- 1999-12-02 AR ARP990106128A patent/AR035006A1/es unknown
- 1999-12-02 EG EG154299A patent/EG24025A/xx active
- 1999-12-03 AU AU17502/00A patent/AU754408B2/en not_active Ceased
- 1999-12-03 ID IDW00200101183A patent/ID28811A/id unknown
- 1999-12-03 CZ CZ20011963A patent/CZ20011963A3/cs unknown
- 1999-12-03 PL PL99348702A patent/PL195973B1/pl not_active IP Right Cessation
- 1999-12-03 KR KR1020017006937A patent/KR100620485B1/ko not_active Expired - Fee Related
- 1999-12-03 JP JP2000586330A patent/JP4481504B2/ja not_active Expired - Fee Related
- 1999-12-03 CA CA002353415A patent/CA2353415A1/en not_active Abandoned
- 1999-12-03 SI SI9930700T patent/SI1146874T1/xx unknown
- 1999-12-03 PT PT99960647T patent/PT1146874E/pt unknown
- 1999-12-03 CN CNB998159735A patent/CN1147300C/zh not_active Expired - Fee Related
- 1999-12-03 AT AT99960647T patent/ATE277043T1/de not_active IP Right Cessation
- 1999-12-03 WO PCT/US1999/028662 patent/WO2000033838A1/en not_active Ceased
- 1999-12-03 OA OA1200100139A patent/OA11724A/en unknown
- 1999-12-03 AP APAP/P/2001/002156A patent/AP1534A/en active
- 1999-12-03 HU HU0104804A patent/HUP0104804A3/hu unknown
- 1999-12-03 DE DE69920518T patent/DE69920518T2/de not_active Expired - Lifetime
- 1999-12-03 SK SK745-2001A patent/SK7452001A3/sk unknown
- 1999-12-03 US US09/857,316 patent/US6495560B1/en not_active Expired - Lifetime
- 1999-12-03 EA EA200100618A patent/EA003254B1/ru not_active IP Right Cessation
- 1999-12-03 ES ES99960647T patent/ES2229798T3/es not_active Expired - Lifetime
- 1999-12-03 HK HK02101522.3A patent/HK1042037B/en not_active IP Right Cessation
- 1999-12-03 DK DK99960647T patent/DK1146874T3/da active
- 1999-12-03 NZ NZ511876A patent/NZ511876A/xx unknown
- 1999-12-03 BR BR9915879-5A patent/BR9915879A/pt not_active Application Discontinuation
- 1999-12-03 IL IL14339099A patent/IL143390A0/xx active IP Right Grant
- 1999-12-03 TR TR2001/01654T patent/TR200101654T2/xx unknown
- 1999-12-03 EP EP99960647A patent/EP1146874B1/en not_active Expired - Lifetime
2001
- 2001-05-24 IL IL143390A patent/IL143390A/en not_active IP Right Cessation
- 2001-05-29 ZA ZA200104398A patent/ZA200104398B/en unknown
- 2001-06-01 NO NO20012732A patent/NO318895B1/no not_active IP Right Cessation
- 2001-06-01 MA MA26218A patent/MA25265A1/fr unknown
- 2001-06-26 BG BG105651A patent/BG65118B1/bg unknown

Also Published As

Publication number	Publication date
CA2353415A1 (en)	2000-06-15
UY25824A1 (es)	2001-07-31
BG105651A (en)	2002-02-28
IL143390A (en)	2006-07-05
PE20001563A1 (es)	2001-02-09
DK1146874T3 (da)	2005-01-31
ZA200104398B (en)	2002-05-29
ID28811A (id)	2001-07-05
EG24025A (en)	2008-03-26
HK1042037A1 (en)	2002-08-02
CZ20011963A3 (cs)	2001-11-14
SK7452001A3 (en)	2001-12-03
NO20012732D0 (no)	2001-06-01
ES2229798T3 (es)	2005-04-16
JP2003523931A (ja)	2003-08-12
AU754408B2 (en)	2002-11-14
EP1146874B1 (en)	2004-09-22
CN1147300C (zh)	2004-04-28
DZ2954A1 (fr)	2004-06-20
NO318895B1 (no)	2005-05-18
HK1042037B (en)	2005-07-29
KR20010080669A (ko)	2001-08-22
BG65118B1 (bg)	2007-03-30
OA11724A (en)	2005-01-26
PT1146874E (pt)	2005-02-28
JP4481504B2 (ja)	2010-06-16
EP1146874A4 (en)	2002-06-05
AP1534A (en)	2006-01-09
TR200101654T2 (tr)	2002-03-21
CO5150166A1 (es)	2002-04-29
HUP0104804A2 (hu)	2002-05-29
IL143390A0 (en)	2002-04-21
SI1146874T1 (en)	2005-04-30
HUP0104804A3 (en)	2002-12-28
DE69920518T2 (de)	2005-09-22
MA25265A1 (fr)	2001-10-01
DE69920518D1 (de)	2004-10-28
PL348702A1 (en)	2002-06-03
CN1334730A (zh)	2002-02-06
ATE277043T1 (de)	2004-10-15
AU1750200A (en)	2000-06-26
TW482673B (en)	2002-04-11
PL195973B1 (pl)	2007-11-30
BR9915879A (pt)	2002-02-13
NZ511876A (en)	2004-02-27
WO2000033838A1 (en)	2000-06-15
NO20012732L (no)	2001-08-01
KR100620485B1 (ko)	2006-09-13
EP1146874A1 (en)	2001-10-24
EA200100618A1 (ru)	2001-12-24
AR035006A1 (es)	2004-04-14
EA003254B1 (ru)	2003-02-27
US6495560B1 (en)	2002-12-17

Publication	Publication Date	Title
JP2001508067A (ja)	2001-06-19	ビトロネクチン受容体アンタゴニスト
AU9577498A (en)	1999-04-12	Vitronectin receptor antagonist
SK4082000A3 (en)	2000-09-12	COMPOUND CONTAINING DIBENZOCYCLOHEPTENE NUCLEUS, PROCESS FOR THEì (54) PRODUCTION THEREOF, PHARMACEUTICAL COMPOSITION CONTA
WO1999015178A1 (en)	1999-04-01	Vitronectin receptor antagonist
EP1146874B1 (en)	2004-09-22	Vitronectin receptor antagonist
AU768918B2 (en)	2004-01-08	Vitronectin receptor antagonists
US20020019387A1 (en)	2002-02-14	Vitronectin receptor antagonist
AU5336299A (en)	2000-02-28	Vitronectin receptor antagonists
US20030216377A1 (en)	2003-11-20	Vitronectin receptor antagonist
MXPA01005547A (en)	2001-12-04	Vitronectin receptor antagonist
MXPA00002895A (en)	2001-12-04	Vitronectin receptor antagonist
MXPA00002700A (en)	2002-03-26	Vitronectin receptor antagonists
MXPA01001386A (en)	2001-09-07	Vitronectin receptor antagonists