HU229307B1

HU229307B1 - Carboxylic acid derivatives that inhibit the binding of integrins to their receptors

Carboxylic acid derivatives that inhibit the binding of integrins to their receptors Download PDF

Info

Publication number: HU229307B1
Authority: HU; Hungary
Prior art keywords: oxo; alkyl; methyl; acid; group
Prior art date: 1999-05-07

Application number

HU0201539A

Other languages

English (en)

Hungarian (hu)

Inventor

Ronald J Biediger

Qi Chen

George William Holland

Jamal M Kassir

Wen Li

Robert V Market

Ian L Scott

Chengde Wu

Original Assignee

Encysive Pharmaceuticals Inc

Priority date

1999-05-07

Filing date

2000-05-05

Publication date

2013-10-28

2000-05-05 Application filed by Encysive Pharmaceuticals Inc filed Critical Encysive Pharmaceuticals Inc

2000-05-05 Priority claimed from PCT/US2000/012303 external-priority patent/WO2000067746A1/en

2002-08-28 Publication of HUP0201539A2 publication Critical patent/HUP0201539A2/hu

2003-07-28 Publication of HUP0201539A3 publication Critical patent/HUP0201539A3/hu

2013-10-28 Publication of HU229307B1 publication Critical patent/HU229307B1/hu

Links

108010044426 integrins Proteins 0.000 title description 9
102000006495 integrins Human genes 0.000 title description 9
150000001732 carboxylic acid derivatives Chemical class 0.000 title description 6
108020003175 receptors Proteins 0.000 title description 2
102000005962 receptors Human genes 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 158
-1 cyano, carboxyl Chemical group 0.000 claims description 136
239000002253 acid Substances 0.000 claims description 99
125000000217 alkyl group Chemical group 0.000 claims description 71
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 60
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 57
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 57
235000019260 propionic acid Nutrition 0.000 claims description 55
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 54
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 52
125000003118 aryl group Chemical group 0.000 claims description 41
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 39
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 31
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 27
125000003545 alkoxy group Chemical group 0.000 claims description 26
239000001257 hydrogen Substances 0.000 claims description 26
229910052739 hydrogen Inorganic materials 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 25
125000003342 alkenyl group Chemical group 0.000 claims description 23
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
229910052757 nitrogen Inorganic materials 0.000 claims description 22
125000003710 aryl alkyl group Chemical group 0.000 claims description 20
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
125000001424 substituent group Chemical group 0.000 claims description 20
239000003814 drug Substances 0.000 claims description 16
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
125000000623 heterocyclic group Chemical group 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
125000000304 alkynyl group Chemical group 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 14
KDYOFXPLHVSIHS-UHFFFAOYSA-N 2-(4-methylphenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=C(C)C=C1 KDYOFXPLHVSIHS-UHFFFAOYSA-N 0.000 claims description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002431 hydrogen Chemical class 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 6
125000003282 alkyl amino group Chemical group 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
238000011282 treatment Methods 0.000 claims description 6
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 5
125000001931 aliphatic group Chemical group 0.000 claims description 5
125000004104 aryloxy group Chemical group 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 claims description 4
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
125000005647 linker group Chemical group 0.000 claims description 4
125000004043 oxo group Chemical group O=* 0.000 claims description 4
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
239000005606 Pyridate Substances 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000002877 alkyl aryl group Chemical group 0.000 claims description 3
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
125000003435 aroyl group Chemical group 0.000 claims description 3
150000005347 biaryls Chemical group 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
150000002081 enamines Chemical class 0.000 claims description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
125000005000 thioaryl group Chemical group 0.000 claims description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
LDYGRLNSOKABMM-UHFFFAOYSA-N 3-(p-tolyl)propionic acid Chemical compound CC1=CC=C(CCC(O)=O)C=C1 LDYGRLNSOKABMM-UHFFFAOYSA-N 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
125000006323 alkenyl amino group Chemical group 0.000 claims description 2
125000001769 aryl amino group Chemical group 0.000 claims description 2
125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 2
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
150000002084 enol ethers Chemical class 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000006574 non-aromatic ring group Chemical group 0.000 claims description 2
229940124530 sulfonamide Drugs 0.000 claims description 2
150000003456 sulfonamides Chemical class 0.000 claims description 2
125000000101 thioether group Chemical group 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
241001122767 Theaceae Species 0.000 claims 2
125000004438 haloalkoxy group Chemical group 0.000 claims 2
KRZJRNZICWNMOA-GXSJLCMTSA-N (3s,4r)-4,8-dihydroxy-3-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2[C@@H](O)[C@@H](OC)CC(=O)C2=C1O KRZJRNZICWNMOA-GXSJLCMTSA-N 0.000 claims 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 claims 1
206010011878 Deafness Diseases 0.000 claims 1
125000003302 alkenyloxy group Chemical group 0.000 claims 1
125000005741 alkyl alkenyl group Chemical group 0.000 claims 1
125000005213 alkyl heteroaryl group Chemical group 0.000 claims 1
210000004556 brain Anatomy 0.000 claims 1
150000003857 carboxamides Chemical class 0.000 claims 1
150000004985 diamines Chemical class 0.000 claims 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
229960003722 doxycycline Drugs 0.000 claims 1
XQTWDDCIUJNLTR-CVHRZJFOSA-N doxycycline monohydrate Chemical compound O.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@@H]1[C@H]2O XQTWDDCIUJNLTR-CVHRZJFOSA-N 0.000 claims 1
OOYGSFOGFJDDHP-KMCOLRRFSA-N kanamycin A sulfate Chemical group OS(O)(=O)=O.O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N OOYGSFOGFJDDHP-KMCOLRRFSA-N 0.000 claims 1
SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 claims 1
229960005489 paracetamol Drugs 0.000 claims 1
229930195734 saturated hydrocarbon Natural products 0.000 claims 1
125000003107 substituted aryl group Chemical group 0.000 claims 1
125000005309 thioalkoxy group Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 168
239000000243 solution Substances 0.000 description 124
239000000203 mixture Substances 0.000 description 108
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
229920006395 saturated elastomer Polymers 0.000 description 68
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 67
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 66
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 63
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
239000000706 filtrate Substances 0.000 description 60
235000019439 ethyl acetate Nutrition 0.000 description 56
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 50
239000011541 reaction mixture Substances 0.000 description 49
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 33
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
239000011780 sodium chloride Substances 0.000 description 32
239000000741 silica gel Substances 0.000 description 28
229910002027 silica gel Inorganic materials 0.000 description 28
239000007787 solid Substances 0.000 description 28
239000012044 organic layer Substances 0.000 description 26
210000004027 cell Anatomy 0.000 description 25
238000002360 preparation method Methods 0.000 description 23
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 22
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
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238000009472 formulation Methods 0.000 description 17
238000000034 method Methods 0.000 description 17
238000004587 chromatography analysis Methods 0.000 description 16
235000017557 sodium bicarbonate Nutrition 0.000 description 16
229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
239000012074 organic phase Substances 0.000 description 15
238000000746 purification Methods 0.000 description 15
238000003756 stirring Methods 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 14
239000007864 aqueous solution Substances 0.000 description 14
210000000265 leukocyte Anatomy 0.000 description 14
239000000047 product Substances 0.000 description 14
239000011734 sodium Substances 0.000 description 13
229910052708 sodium Inorganic materials 0.000 description 13
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 12
238000006243 chemical reaction Methods 0.000 description 12
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150000001408 amides Chemical class 0.000 description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
229940079593 drug Drugs 0.000 description 11
235000019441 ethanol Nutrition 0.000 description 11
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102100023543 Vascular cell adhesion protein 1 Human genes 0.000 description 10
239000004480 active ingredient Substances 0.000 description 10
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210000001519 tissue Anatomy 0.000 description 10
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125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 description 9
229910052799 carbon Inorganic materials 0.000 description 9
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239000000843 powder Substances 0.000 description 9
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
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UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
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150000001412 amines Chemical class 0.000 description 7
201000010099 disease Diseases 0.000 description 7
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239000003795 chemical substances by application Substances 0.000 description 6
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230000005764 inhibitory process Effects 0.000 description 6
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