BG108004A - Карбамидни производни като интегрин алфа 4 антагонисти - Google Patents
Карбамидни производни като интегрин алфа 4 антагонисти Download PDFInfo
- Publication number
- BG108004A BG108004A BG108004A BG10800403A BG108004A BG 108004 A BG108004 A BG 108004A BG 108004 A BG108004 A BG 108004A BG 10800403 A BG10800403 A BG 10800403A BG 108004 A BG108004 A BG 108004A
- Authority
- BG
- Bulgaria
- Prior art keywords
- phenyl
- propionic acid
- ureido
- alkyl
- dichlorobenzoylamino
- Prior art date
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- 239000005557 antagonist Substances 0.000 title claims description 5
- 102100032818 Integrin alpha-4 Human genes 0.000 title description 3
- 150000003672 ureas Chemical class 0.000 title description 3
- 108010041012 Integrin alpha4 Proteins 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 108010008212 Integrin alpha4beta1 Proteins 0.000 claims abstract description 8
- -1 3,5-dichloropyridine-4-carbonylamino Chemical group 0.000 claims description 659
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 419
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 403
- 150000001875 compounds Chemical class 0.000 claims description 395
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 236
- 235000019260 propionic acid Nutrition 0.000 claims description 157
- 125000000217 alkyl group Chemical group 0.000 claims description 138
- 238000000034 method Methods 0.000 claims description 112
- 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 84
- 125000003118 aryl group Chemical group 0.000 claims description 60
- 125000001424 substituent group Chemical group 0.000 claims description 60
- 125000001072 heteroaryl group Chemical group 0.000 claims description 48
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims description 42
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 37
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 36
- 125000000623 heterocyclic group Chemical group 0.000 claims description 36
- 125000003342 alkenyl group Chemical group 0.000 claims description 34
- 125000000304 alkynyl group Chemical group 0.000 claims description 34
- 108010044426 integrins Proteins 0.000 claims description 33
- 102000006495 integrins Human genes 0.000 claims description 33
- 150000001412 amines Chemical class 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 239000012948 isocyanate Substances 0.000 claims description 15
- 150000002513 isocyanates Chemical class 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 230000001575 pathological effect Effects 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- 230000008485 antagonism Effects 0.000 claims description 8
- 230000021164 cell adhesion Effects 0.000 claims description 8
- 230000006872 improvement Effects 0.000 claims description 8
- 150000002540 isothiocyanates Chemical class 0.000 claims description 8
- HZQQXUYULYYXPY-UHFFFAOYSA-N methyl 2-[(2-piperidin-1-ylsulfonylphenyl)carbamoylamino]propanoate Chemical compound COC(C(C)NC(=O)NC1=C(C=CC=C1)S(=O)(=O)N1CCCCC1)=O HZQQXUYULYYXPY-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 210000000056 organ Anatomy 0.000 claims description 8
- 206010061218 Inflammation Diseases 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
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- 230000002757 inflammatory effect Effects 0.000 claims description 7
- 230000004054 inflammatory process Effects 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 238000002054 transplantation Methods 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 201000008383 nephritis Diseases 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 5
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- 208000019693 Lung disease Diseases 0.000 claims description 5
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- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
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- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- 201000006474 Brain Ischemia Diseases 0.000 claims description 4
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 4
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- 208000009525 Myocarditis Diseases 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 206010008118 cerebral infarction Diseases 0.000 claims description 4
- 208000010247 contact dermatitis Diseases 0.000 claims description 4
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- 230000002401 inhibitory effect Effects 0.000 claims description 4
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- 206010053555 Arthritis bacterial Diseases 0.000 claims description 3
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- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 3
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 238000010322 bone marrow transplantation Methods 0.000 claims description 3
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
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- 208000026278 immune system disease Diseases 0.000 claims description 3
- JTRPNOJLPDTCHI-MHZLTWQESA-N methyl (2s)-2-[[2-(cyclohexylmethylcarbamoyl)phenyl]carbamoylamino]-3-[4-[(2,6-dichlorobenzoyl)amino]phenyl]propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)NC=1C(=CC=CC=1)C(=O)NCC1CCCCC1)C(C=C1)=CC=C1NC(=O)C1=C(Cl)C=CC=C1Cl JTRPNOJLPDTCHI-MHZLTWQESA-N 0.000 claims description 3
- JPYVYRCJNDBGIP-DEOSSOPVSA-N methyl (2s)-3-[4-[(2,6-dichlorobenzoyl)amino]phenyl]-2-[(2-piperidin-1-ylsulfonylphenyl)carbamoylamino]propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)NC=1C(=CC=CC=1)S(=O)(=O)N1CCCCC1)C(C=C1)=CC=C1NC(=O)C1=C(Cl)C=CC=C1Cl JPYVYRCJNDBGIP-DEOSSOPVSA-N 0.000 claims description 3
- ABDCXEYJDDVTLD-SANMLTNESA-N methyl (2s)-3-[4-[(2,6-dichlorobenzoyl)amino]phenyl]-2-[[2-(4-methylphenyl)sulfonyl-5-(trifluoromethyl)phenyl]carbamoylamino]propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)NC=1C(=CC=C(C=1)C(F)(F)F)S(=O)(=O)C=1C=CC(C)=CC=1)C(C=C1)=CC=C1NC(=O)C1=C(Cl)C=CC=C1Cl ABDCXEYJDDVTLD-SANMLTNESA-N 0.000 claims description 3
- LBMVPUQWZVQKNU-VWLOTQADSA-N methyl (2s)-3-[4-[(2,6-dichlorobenzoyl)amino]phenyl]-2-[[2-(4-methylphenyl)sulfonylpyridin-3-yl]carbamoylamino]propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)NC=1C(=NC=CC=1)S(=O)(=O)C=1C=CC(C)=CC=1)C(C=C1)=CC=C1NC(=O)C1=C(Cl)C=CC=C1Cl LBMVPUQWZVQKNU-VWLOTQADSA-N 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 229910052702 rhenium Inorganic materials 0.000 claims description 3
- 201000001223 septic arthritis Diseases 0.000 claims description 3
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 2
- OHBQPCCCRFSCAX-UHFFFAOYSA-N Hydroquinone dimethyl ether Natural products COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 229940024472 emollients and protectives carbamide product Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- RYRTVAYCGLDSRN-SANMLTNESA-N methyl (2s)-2-[[2-(cyclohexylmethylcarbamoyl)-6-methoxyphenyl]carbamoylamino]-3-[4-[(2,6-dichlorobenzoyl)amino]phenyl]propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)NC=1C(=CC=CC=1OC)C(=O)NCC1CCCCC1)C(C=C1)=CC=C1NC(=O)C1=C(Cl)C=CC=C1Cl RYRTVAYCGLDSRN-SANMLTNESA-N 0.000 claims description 2
- MUVFAYIVUAITJK-SANMLTNESA-N methyl (2s)-2-[[2-(cyclohexylmethylsulfamoyl)phenyl]carbamoylamino]-3-[4-[(2,6-dichlorobenzoyl)amino]phenyl]propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)NC=1C(=CC=CC=1)S(=O)(=O)NCC1CCCCC1)C(C=C1)=CC=C1NC(=O)C1=C(Cl)C=CC=C1Cl MUVFAYIVUAITJK-SANMLTNESA-N 0.000 claims description 2
- KRKVSAMBXMLPDZ-MHZLTWQESA-N methyl (2s)-2-[[2-chloro-5-(4-methylphenyl)sulfonylphenyl]carbamoylamino]-3-[4-[(2,6-dichlorobenzoyl)amino]phenyl]propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)NC=1C(=CC=C(C=1)S(=O)(=O)C=1C=CC(C)=CC=1)Cl)C(C=C1)=CC=C1NC(=O)C1=C(Cl)C=CC=C1Cl KRKVSAMBXMLPDZ-MHZLTWQESA-N 0.000 claims description 2
- IMYTXXPZTPCZRL-MHZLTWQESA-N methyl (2s)-2-[[[2-(cyclohexylmethylcarbamoyl)phenyl]-methylcarbamoyl]amino]-3-[4-[(2,6-dichlorobenzoyl)amino]phenyl]propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)N(C)C=1C(=CC=CC=1)C(=O)NCC1CCCCC1)C(C=C1)=CC=C1NC(=O)C1=C(Cl)C=CC=C1Cl IMYTXXPZTPCZRL-MHZLTWQESA-N 0.000 claims description 2
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Classifications
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- 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
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- 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
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- 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
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
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- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
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- 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
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- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
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Applications Claiming Priority (2)
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ES200100126A ES2200617B1 (es) | 2001-01-19 | 2001-01-19 | Derivados de urea como antagonistas de integrinas alfa 4. |
PCT/EP2002/000331 WO2002057242A2 (en) | 2001-01-19 | 2002-01-15 | Urea derivatives as integrin alpha 4 antagonists |
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Family
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BG108004A BG108004A (bg) | 2001-01-19 | 2003-07-18 | Карбамидни производни като интегрин алфа 4 антагонисти |
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JP (1) | JP4173003B2 (es) |
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CN (1) | CN100536839C (es) |
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AT (1) | ATE374191T1 (es) |
AU (1) | AU2002228048B2 (es) |
BG (1) | BG108004A (es) |
BR (1) | BR0206588A (es) |
CA (1) | CA2434939A1 (es) |
CY (1) | CY1107086T1 (es) |
CZ (1) | CZ20031964A3 (es) |
DE (1) | DE60222647T2 (es) |
DK (1) | DK1383750T3 (es) |
EC (1) | ECSP034707A (es) |
EE (1) | EE200300327A (es) |
ES (2) | ES2200617B1 (es) |
HK (1) | HK1058361A1 (es) |
HU (1) | HUP0303722A3 (es) |
IL (1) | IL156939A0 (es) |
MX (1) | MXPA03006363A (es) |
MY (1) | MY129423A (es) |
NO (1) | NO327002B1 (es) |
NZ (1) | NZ527031A (es) |
PL (1) | PL369120A1 (es) |
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UA (1) | UA81603C2 (es) |
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WO (1) | WO2002057242A2 (es) |
ZA (1) | ZA200305535B (es) |
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WO2005019193A2 (en) * | 2003-08-20 | 2005-03-03 | Smithkline Beecham Corporation | Phenylurea derivatives useful in the treatment of conditions mediated by polo-like kinases (plk) |
JP5170386B2 (ja) | 2005-08-18 | 2013-03-27 | 日産化学工業株式会社 | スルフォニル基を有するチオフェン化合物及びその製造法 |
CN101360736A (zh) * | 2005-11-23 | 2009-02-04 | 阿斯利康(瑞典)有限公司 | L-丙氨酸衍生物 |
KR100588821B1 (ko) * | 2006-01-06 | 2006-06-12 | 모악개발 주식회사 | 균일 팽창이 가능한 패커를 구비하는 하수관로 부분보수장치 |
US20080045521A1 (en) * | 2006-06-09 | 2008-02-21 | Astrazeneca Ab | Phenylalanine derivatives |
WO2008093065A1 (en) * | 2007-01-29 | 2008-08-07 | Astrazeneca Ab | L-ALANINE DERIVATIVES AS α5βL ANTAGONISTS |
NZ578744A (en) * | 2007-01-31 | 2012-02-24 | Vertex Pharma | 2-aminopyridine derivatives useful as kinase inhibitors |
ES2320955B1 (es) | 2007-03-02 | 2010-03-16 | Laboratorios Almirall S.A. | Nuevos derivados de 3-((1,2,4)triazolo(4,3-a)piridin-7-il)benzamida. |
WO2008125811A1 (en) * | 2007-04-11 | 2008-10-23 | Astrazeneca Ab | N-[HETEROARYLCARBONYL]-S-THIENYL-L-ALANINE DERIVATIVES AS α5β1 ANTAGONISTS |
EP2108641A1 (en) | 2008-04-11 | 2009-10-14 | Laboratorios Almirall, S.A. | New substituted spiro[cycloalkyl-1,3'-indo]-2'(1'H)-one derivatives and their use as p38 mitogen-activated kinase inhibitors |
EP2113503A1 (en) | 2008-04-28 | 2009-11-04 | Laboratorios Almirall, S.A. | New substituted indolin-2-one derivatives and their use as p39 mitogen-activated kinase inhibitors |
US8569337B2 (en) | 2008-07-23 | 2013-10-29 | Vertex Pharmaceuticals Incorporated | Tri-cyclic pyrazolopyridine kinase inhibitors |
CA2731451A1 (en) | 2008-07-23 | 2010-01-28 | Vertex Pharmaceuticals Incorporated | Pyrazolopyridine kinase inhibitors |
JP5631310B2 (ja) | 2008-07-23 | 2014-11-26 | バーテックス ファーマシューティカルズ インコーポレイテッドVertex Pharmaceuticals Incorporated | 三環式ピラゾロピリジンキナーゼ阻害剤 |
AU2009279611A1 (en) | 2008-08-06 | 2010-02-11 | Vertex Pharmaceuticals Incorporated | Aminopyridine kinase inhibitors |
KR101038486B1 (ko) * | 2008-09-03 | 2011-06-01 | 쌍용건설 주식회사 | 패커를 이용한 비굴착식 하수관로 보수 장치 및 방법 |
US8211401B2 (en) * | 2008-12-05 | 2012-07-03 | Molecular Insight Pharmaceuticals, Inc. | Technetium- and rhenium-bis(heteroaryl) complexes and methods of use thereof for inhibiting PSMA |
AU2010245914A1 (en) | 2009-05-06 | 2011-12-15 | Vertex Pharmaceuticals Incorporated | Pyrazolopyridines |
FI20095678A0 (fi) * | 2009-06-16 | 2009-06-16 | Biotie Therapies Oy | Ureasubstituoituja sulfoniamidijohdannaisia |
EP2322176A1 (en) | 2009-11-11 | 2011-05-18 | Almirall, S.A. | New 7-phenyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one derivatives |
EP2528917B1 (en) | 2010-01-27 | 2016-10-19 | Vertex Pharmaceuticals Incorporated | Pyrazolopyridines useful for the treatment of autoimmune, inflammatory or (hyper)proliferative diseases |
CA2787079A1 (en) | 2010-01-27 | 2011-08-04 | Vertex Pharmaceuticals Incorporated | Pyrazolopyrazine kinase inhibitors |
CA2787363A1 (en) | 2010-01-27 | 2011-08-04 | Vertex Pharmaceuticals Incorporated | Pyrazolopyrimidine kinase inhibitors |
US20130273034A1 (en) * | 2010-09-03 | 2013-10-17 | Kenneth W. Bair | Novel compounds and compositions for the inhibition of nampt |
ES2968371T3 (es) | 2013-10-10 | 2024-05-09 | Eastern Virginia Medical School | Derivados de 4-((2-hidroxi-3-metoxibencil)amino) bencenosulfonamida como inhibidores de la 12-lipoxigenasa |
KR20240015737A (ko) | 2018-10-30 | 2024-02-05 | 길리애드 사이언시즈, 인코포레이티드 | 알파4베타7 인테그린 억제제로서의 퀴놀린 유도체 |
AU2019373245C1 (en) | 2018-10-30 | 2022-10-27 | Gilead Sciences, Inc. | Compounds for inhibition of alpha 4β7 integrin |
WO2020092394A1 (en) | 2018-10-30 | 2020-05-07 | Gilead Sciences, Inc. | Imidazopyridine derivatives as alpha4beta7 integrin inhibitors |
CA3115820A1 (en) | 2018-10-30 | 2020-05-07 | Gilead Sciences, Inc. | Compounds for inhibition of .alpha.4.beta.7 integrin |
US11578069B2 (en) | 2019-08-14 | 2023-02-14 | Gilead Sciences, Inc. | Compounds for inhibition of α4 β7 integrin |
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ATE298338T1 (de) | 1997-12-17 | 2005-07-15 | Merck & Co Inc | Integrin-rezeptor-antagonisten |
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DE60009883T2 (de) | 1999-03-01 | 2005-04-07 | Elan Pharmaceuticals, Inc., San Francisco | Alpha-aminoessigsäure derivate als alpha 4 beta 7- rezeptor antagonisten |
DE19909979A1 (de) * | 1999-03-06 | 2000-09-07 | Bayer Ag | Verfahren zur Herstellung von Glycokonjugaten von 20(S)-Camptothecin |
DK1176956T3 (da) | 1999-05-07 | 2008-05-26 | Encysive Pharmaceuticals Inc | Carboxylsyrederivater, som inhiberer bindingen af integriner til deres receptorer |
US6518283B1 (en) | 1999-05-28 | 2003-02-11 | Celltech R&D Limited | Squaric acid derivatives |
AU6909300A (en) * | 1999-08-20 | 2001-03-19 | Merck & Co., Inc. | Substituted ureas as cell adhesion inhibitors |
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- 2002-01-18 MY MYPI20020184A patent/MY129423A/en unknown
- 2002-01-18 AR ARP020100181A patent/AR032256A1/es unknown
- 2002-01-18 UY UY27127A patent/UY27127A1/es unknown
-
2003
- 2003-07-17 ZA ZA200305535A patent/ZA200305535B/en unknown
- 2003-07-18 EC EC2003004707A patent/ECSP034707A/es unknown
- 2003-07-18 NO NO20033269A patent/NO327002B1/no not_active IP Right Cessation
- 2003-07-18 BG BG108004A patent/BG108004A/bg unknown
-
2004
- 2004-02-18 HK HK04101137A patent/HK1058361A1/xx not_active IP Right Cessation
-
2007
- 2007-05-21 US US11/802,165 patent/US20070238763A1/en not_active Abandoned
- 2007-12-13 CY CY20071101582T patent/CY1107086T1/el unknown
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