SK286696B6 - Deriváty karboxylovej kyseliny ako inhibítory väzby integrínov na svoje receptory, farmaceutická kompozícia obsahujúca ich a ich použitie - Google Patents

Deriváty karboxylovej kyseliny ako inhibítory väzby integrínov na svoje receptory, farmaceutická kompozícia obsahujúca ich a ich použitie Download PDF

Info

Publication number: SK286696B6
Authority: SK; Slovakia
Prior art keywords: amino; methyl; carbonyl; oxo; dihydro
Prior art date: 1999-05-07

Application number

SK1608-2001A

Other languages

English (en)

Slovak (sk)

Other versions

SK16082001A3 (sk

Inventor

Ronald J. Biediger

Qi Chen

George W. Holland

Jamal M. Kassir

Wen Li

Robert V. Market

Ian L. Scott

Chengde Wu

Original Assignee

Texas Biotechnology Corporation

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.)

1999-05-07

Filing date

2000-05-05

Publication date

2009-03-05

2000-05-05 Application filed by Texas Biotechnology Corporation filed Critical Texas Biotechnology Corporation

2002-04-04 Publication of SK16082001A3 publication Critical patent/SK16082001A3/sk

2009-03-05 Publication of SK286696B6 publication Critical patent/SK286696B6/sk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 112
108010044426 integrins Proteins 0.000 title claims abstract description 20
102000006495 integrins Human genes 0.000 title claims abstract description 20
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 14
239000003112 inhibitor Substances 0.000 title abstract description 7
102000005962 receptors Human genes 0.000 title abstract description 3
108020003175 receptors Proteins 0.000 title abstract description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 title description 3
239000003814 drug Substances 0.000 claims abstract description 20
230000002401 inhibitory effect Effects 0.000 claims abstract description 10
241000124008 Mammalia Species 0.000 claims abstract description 8
238000004519 manufacturing process Methods 0.000 claims abstract description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 310
-1 nitro, amino Chemical group 0.000 claims description 233
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 184
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 145
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 description 116
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 96
125000000217 alkyl group Chemical group 0.000 claims description 62
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 58
235000019260 propionic acid Nutrition 0.000 claims description 58
125000003118 aryl group Chemical group 0.000 claims description 42
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 41
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 35
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 35
229920006395 saturated elastomer Polymers 0.000 claims description 33
229910052739 hydrogen Inorganic materials 0.000 claims description 27
125000003342 alkenyl group Chemical group 0.000 claims description 26
125000003545 alkoxy group Chemical group 0.000 claims description 25
239000001257 hydrogen Substances 0.000 claims description 25
125000001424 substituent group Chemical group 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 21
125000000304 alkynyl group Chemical group 0.000 claims description 19
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
125000000623 heterocyclic group Chemical group 0.000 claims description 18
150000002367 halogens Chemical class 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 16
125000003282 alkyl amino group Chemical group 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 15
125000000753 cycloalkyl group Chemical group 0.000 claims description 15
KNTDPRHBTCOYNN-IBGZPJMESA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-6-methyl-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(O)C=C(C)N1CC1=CC=CC=C1Cl KNTDPRHBTCOYNN-IBGZPJMESA-N 0.000 claims description 14
125000003710 aryl alkyl group Chemical group 0.000 claims description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 13
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 13
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 12
125000001188 haloalkyl group Chemical group 0.000 claims description 10
125000005309 thioalkoxy group Chemical group 0.000 claims description 10
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 9
150000003857 carboxamides Chemical class 0.000 claims description 9
125000000068 chlorophenyl group Chemical group 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 8
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
125000006323 alkenyl amino group Chemical group 0.000 claims description 7
125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
125000004181 carboxyalkyl group Chemical group 0.000 claims description 6
125000004663 dialkyl amino group Chemical group 0.000 claims description 6
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
125000005000 thioaryl group Chemical group 0.000 claims description 6
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
125000002877 alkyl aryl group Chemical group 0.000 claims description 5
150000001408 amides Chemical class 0.000 claims description 5
125000003435 aroyl group Chemical group 0.000 claims description 5
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
125000004104 aryloxy group Chemical group 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
150000002081 enamines Chemical class 0.000 claims description 5
125000004043 oxo group Chemical group O=* 0.000 claims description 5
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 5
125000004434 sulfur atom Chemical group 0.000 claims description 5
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
125000002619 bicyclic group Chemical group 0.000 claims description 4
125000004986 diarylamino group Chemical group 0.000 claims description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
LLPUNNOFVNYJJQ-VWLOTQADSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-2-oxo-4-phenylpyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(C=2C=CC=CC=2)C=CN1CC1=CC=CC=C1Cl LLPUNNOFVNYJJQ-VWLOTQADSA-N 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
150000001298 alcohols Chemical class 0.000 claims description 3
125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 3
125000001769 aryl amino group Chemical group 0.000 claims description 3
150000005347 biaryls Chemical group 0.000 claims description 3
MVHPKFQBHWGTQH-UHFFFAOYSA-N cyano(nitro)carbamic acid Chemical class OC(=O)N(C#N)[N+]([O-])=O MVHPKFQBHWGTQH-UHFFFAOYSA-N 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
150000002170 ethers Chemical class 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
150000003457 sulfones Chemical class 0.000 claims description 3
150000003568 thioethers Chemical class 0.000 claims description 3
229910052727 yttrium Inorganic materials 0.000 claims description 3
WMKLRNMTKRPGEL-FQEVSTJZSA-N (3s)-3-[[1-[(2-chloro-6-fluorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=C(F)C=CC=C1Cl WMKLRNMTKRPGEL-FQEVSTJZSA-N 0.000 claims description 2
QKZPBAQVDYCGCA-QHCPKHFHSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-[[ethyl(ethylcarbamoyl)carbamoyl]amino]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound O=C1C(NC(=O)N[C@@H](CC(O)=O)C=2C=CC(C)=CC=2)=C(NC(=O)N(CC)C(=O)NCC)C=CN1CC1=CC=CC=C1Cl QKZPBAQVDYCGCA-QHCPKHFHSA-N 0.000 claims description 2
239000000654 additive Substances 0.000 claims description 2
230000000996 additive effect Effects 0.000 claims description 2
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
125000005018 aryl alkenyl group Chemical group 0.000 claims description 2
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 3
QQWKDWJISNTBNF-FQEVSTJZSA-N (3s)-3-[[1-[(2-bromophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=CC=C1Br QQWKDWJISNTBNF-FQEVSTJZSA-N 0.000 claims 1
HRQHUYXBRUCBES-FQEVSTJZSA-N (3s)-3-[[1-[(2-bromophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(C)C=CN1CC1=CC=CC=C1Br HRQHUYXBRUCBES-FQEVSTJZSA-N 0.000 claims 1
MEUVMPSEIBMVOP-FQEVSTJZSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=CC=C1Cl MEUVMPSEIBMVOP-FQEVSTJZSA-N 0.000 claims 1
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JNBGWQREIHPHSK-SFHVURJKSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methoxy-3-methylphenyl)propanoic acid Chemical compound C1=C(C)C(OC)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(O)C=CN1CC1=CC=CC=C1Cl JNBGWQREIHPHSK-SFHVURJKSA-N 0.000 claims 1
PAMQUYCMYTUMJW-KRWDZBQOSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-2-oxopyridin-3-yl]carbamoylamino]-3-[3-(trifluoromethyl)phenyl]propanoic acid Chemical compound N([C@@H](CC(=O)O)C=1C=C(C=CC=1)C(F)(F)F)C(=O)NC(C1=O)=C(O)C=CN1CC1=CC=CC=C1Cl PAMQUYCMYTUMJW-KRWDZBQOSA-N 0.000 claims 1
YYPZHWRKAVHZNN-SFHVURJKSA-N (3s)-3-[[1-[(2-fluorophenyl)methyl]-4-hydroxy-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(O)C=CN1CC1=CC=CC=C1F YYPZHWRKAVHZNN-SFHVURJKSA-N 0.000 claims 1
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125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 description 1
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
238000007614 solvation Methods 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000007480 spreading Effects 0.000 description 1
238000003892 spreading Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
210000000130 stem cell Anatomy 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000003206 sterilizing agent Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
235000011044 succinic acid Nutrition 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid group Chemical group C(CCC(=O)O)(=O)O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 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
150000003512 tertiary amines Chemical class 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000004797 therapeutic response Effects 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
ZPHGMBGIFODUMF-UHFFFAOYSA-N thiophen-2-ylmethanol Chemical compound OCC1=CC=CS1 ZPHGMBGIFODUMF-UHFFFAOYSA-N 0.000 description 1
230000000451 tissue damage Effects 0.000 description 1
231100000827 tissue damage Toxicity 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
239000006208 topical dosage form Substances 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
229960004799 tryptophan Drugs 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229960004295 valine Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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- 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
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Diabetes (AREA)
Pulmonology (AREA)
Physical Education & Sports Medicine (AREA)
Hematology (AREA)
Rheumatology (AREA)
Transplantation (AREA)
Biomedical Technology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Oncology (AREA)
Pain & Pain Management (AREA)
Endocrinology (AREA)
Emergency Medicine (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Obesity (AREA)
Orthopedic Medicine & Surgery (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)

SK1608-2001A 1999-05-07 2000-05-05 Deriváty karboxylovej kyseliny ako inhibítory väzby integrínov na svoje receptory, farmaceutická kompozícia obsahujúca ich a ich použitie SK286696B6 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US13297199P	1999-05-07	1999-05-07
PCT/US2000/012303 WO2000067746A1 (fr)	1999-05-07	2000-05-05	Derives d'acide carboxylique inhibant la liaison entre des integrines et leurs recepteurs

Publications (2)

Publication Number	Publication Date
SK16082001A3 SK16082001A3 (sk)	2002-04-04
SK286696B6 true SK286696B6 (sk)	2009-03-05

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SK1608-2001A SK286696B6 (sk)	1999-05-07	2000-05-05	Deriváty karboxylovej kyseliny ako inhibítory väzby integrínov na svoje receptory, farmaceutická kompozícia obsahujúca ich a ich použitie

Country Status (23)

Country	Link
EP (1)	EP1176956B1 (fr)
JP (1)	JP5132855B2 (fr)
AT (1)	ATE383153T1 (fr)
AU (1)	AU5267900A (fr)
CA (1)	CA2373360C (fr)
CY (1)	CY1107438T1 (fr)
CZ (1)	CZ303312B6 (fr)
DE (1)	DE60037726T2 (fr)
DK (1)	DK1176956T3 (fr)
ES (1)	ES2296625T3 (fr)
IL (2)	IL146311A0 (fr)
IN (1)	IN2001KN01110A (fr)
MX (1)	MXPA01011340A (fr)
NO (1)	NO324421B1 (fr)
NZ (1)	NZ515248A (fr)
PL (1)	PL205322B1 (fr)
RO (1)	RO122246B1 (fr)
RU (1)	RU2263109C2 (fr)
SI (1)	SI20744B (fr)
SK (1)	SK286696B6 (fr)
TR (2)	TR200201920T2 (fr)
WO (1)	WO2000067746A1 (fr)
ZA (1)	ZA200108774B (fr)

Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6972296B2 (en) *	1999-05-07	2005-12-06	Encysive Pharmaceuticals Inc.	Carboxylic acid derivatives that inhibit the binding of integrins to their receptors
US6723711B2 (en) *	1999-05-07	2004-04-20	Texas Biotechnology Corporation	Propanoic acid derivatives that inhibit the binding of integrins to their receptors
AR026748A1 (es)	1999-12-08	2003-02-26	Vertex Pharma	Un compuesto inhibidor de caspasas, una composicion farmaceutica que lo comprende, un metodo para la sintesis del mismo y un compuesto intermediario paradicha sintesis
ES2200617B1 (es)	2001-01-19	2005-05-01	Almirall Prodesfarma, S.A.	Derivados de urea como antagonistas de integrinas alfa 4.
SI21096B (sl) *	2001-10-09	2012-05-31	Encysive Pharmaceuticals Inc	Derivati karboksilne kisline ki inhibirajo vezavo integrinov na njihove receptorje
SI1490064T1 (sl) *	2002-02-14	2010-01-29	Pharmacia Corp	Substituirani piridinoni kot modulatorji p38 MAP kinaze
BR0312232A (pt)	2002-06-28	2005-05-10	Vertex Pharma	Inibidores de caspases e seus usos
CN1703395A (zh)	2002-08-09	2005-11-30	特兰斯泰克制药公司	芳基和杂芳基化合物以及调节凝血的方法
WO2004044046A2 (fr) *	2002-11-08	2004-05-27	Encysive Pharmaceuticals	Produits de combinaison comprenant des derives d'acide carboxylique inhibant la liaison des integrines a leurs recepteurs et autres composes therapeutiques
WO2004058718A1 (fr)	2002-12-20	2004-07-15	Vertex Pharmaceuticals Incorporated	Derives d'esters et d'amides d'acide 4-oxo-3-(1-oxo-1h-isoquinolin-2-ylacetylamino)-pentanoique et leur utilisation en tant qu'inhibiteurs de caspase
PE20050159A1 (es)	2003-05-27	2005-04-19	Vertex Pharma	Derivados de acido 3-[2-(3-amino-2-oxo-2h-piridin-1-il)-acetilamino]-4-oxo-pentanoico como inhibidores de caspasa
JP2007501844A (ja)	2003-08-08	2007-02-01	トランス　テック　ファーマ，インコーポレイテッド	アリール及びヘテロアリール化合物、組成物並びに使用方法
WO2005014532A1 (fr)	2003-08-08	2005-02-17	Transtech Pharma, Inc.	Composes aryle et heteroaryle, compositions et procedes associes
US7208601B2 (en)	2003-08-08	2007-04-24	Mjalli Adnan M M	Aryl and heteroaryl compounds, compositions, and methods of use
EP1917244A2 (fr)	2005-08-24	2008-05-07	Abbott GmbH & Co. KG	Composes guanidine a substitution hetaryl et utilisation en tant que partenaires de liaison pour des recepteurs de 5-ht5
CA2680366C (fr) *	2007-03-09	2016-06-21	University Health Network	Inhibiteur de carnitine palmitoyltransferase et traitement du cancer
CA2677049A1 (fr)	2007-08-01	2009-02-05	Sionex Corporation	Inhibiteurs cycliques de la carnitine palmitoyltransferase et traitement anticancereux
SG175355A1 (en) *	2009-04-27	2011-12-29	Elan Pharm Inc	Pyridinone antagonists of alpha-4 integrins
WO2012033548A2 (fr) *	2010-09-07	2012-03-15	E. I. Du Pont De Nemours And Company	Oxo-hétérocycles et sulfono-hétérocycles bis-azotés herbicides
US8952024B2 (en)	2009-09-09	2015-02-10	E I Du Pont De Nemours And Company	Herbicidal pyrimidone derivatives
AU2013216006B2 (en) *	2012-01-31	2017-06-08	Daiichi Sankyo Company, Limited	Pyridone derivatives
US10227323B2 (en)	2013-09-20	2019-03-12	Biomarin Pharmaceutical Inc.	Glucosylceramide synthase inhibitors for the treatment of diseases
EP3116910A1 (fr)	2014-03-13	2017-01-18	Prothena Biosciences Limited	Polythérapie pour la sclérose en plaques
MX382781B (es)	2014-04-02	2025-03-13	Intermune Inc	Piridinonas anti-fibroticas.
US10875875B2 (en) *	2017-04-26	2020-12-29	Aviara Pharmaceuticals, Inc.	Propionic acid derivatives and methods of use thereof
US10246451B2 (en) *	2017-04-26	2019-04-02	Aviara Pharmaceuticals, Inc.	Propionic acid derivatives and methods of use thereof
CN111093717B (zh) *	2017-04-28	2023-01-31	德克萨斯州儿童医院	靶向性纳米颗粒
CA3090270A1 (fr) *	2018-02-02	2019-08-08	Genentech, Inc.	Compose pharmaceutique, sels de celui-ci, formulations de celui-ci, et procedes de fabrication et d'utilisation de celui-ci
US11179383B2 (en)	2018-10-30	2021-11-23	Gilead Sciences, Inc.	Compounds for inhibition of α4β7 integrin
JP7189368B2 (ja)	2018-10-30	2022-12-13	ギリアードサイエンシーズ，インコーポレイテッド	アルファ４ベータ７インテグリンの阻害のための化合物
KR102630416B1 (ko)	2018-10-30	2024-02-01	길리애드 사이언시즈, 인코포레이티드	알파4베타7 인테그린 억제제로서의 퀴놀린 유도체
WO2020092394A1 (fr)	2018-10-30	2020-05-07	Gilead Sciences, Inc.	Dérivés d'imidazopyridine utilisés en tant qu'inhibiteurs de l'intégrine alpha4bêta7
CN114222730B (zh)	2019-08-14	2024-09-10	吉利德科学公司	用于抑制α4β7整合素的化合物

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2614189A1 (de) *	1976-04-02	1977-10-20	Hoechst Ag	Therapeutisch wirksame ureido- und semicarbazido-derivate des tiazols und verfahren zu ihrer herstellung
US5220017A (en) *	1991-04-10	1993-06-15	Merck & Co., Inc.	Cholecystokinin antagonists
ATE195117T1 (de) *	1993-03-31	2000-08-15	Searle & Co	1-amdinophenyl-pyrrolidone/piperidinone als blutblättchen-aggregations inhibitoren
AU672699B2 (en) *	1993-06-30	1996-10-10	Sankyo Company Limited	Amide and urea derivatives having anti-hypercholesteremic activity, their preparation and their therapeutic uses
US5770573A (en) *	1993-12-06	1998-06-23	Cytel Corporation	CS-1 peptidomimetics, compositions and methods of using the same
JPH07304755A (ja) *	1994-05-12	1995-11-21	Yamanouchi Pharmaceut Co Ltd	縮合ジアゼピン誘導体
US5610296A (en) *	1994-12-05	1997-03-11	G. D. Searle & Co.	Process for the preparation of amidino phenyl pyrrolidine beta-alanine urea analogs
US6306840B1 (en) *	1995-01-23	2001-10-23	Biogen, Inc.	Cell adhesion inhibitors
WO1997043650A1 (fr) *	1996-05-15	1997-11-20	G.D. Searle & Co.	Methode et reactif pour mesurer les taux de composes antiplaquettaires dans le sang
AU723315B2 (en) *	1996-09-18	2000-08-24	Merck & Co., Inc.	Combination therapy for reducing the risks associated with cardiovascular disease
US6025358A (en) *	1998-06-11	2000-02-15	G. D. Searle & Co.	Double prodrugs of potent GP IIb/IIIa antagonists
WO2000017197A1 (fr) *	1998-09-21	2000-03-30	Biochem Pharma Inc.	Quinolizinones inhibiteurs de l'integrine

2000
- 2000-05-05 NZ NZ515248A patent/NZ515248A/xx not_active IP Right Cessation
- 2000-05-05 DE DE60037726T patent/DE60037726T2/de not_active Expired - Lifetime
- 2000-05-05 AU AU52679/00A patent/AU5267900A/en not_active Abandoned
- 2000-05-05 IL IL14631100A patent/IL146311A0/xx active IP Right Grant
- 2000-05-05 DK DK00937527T patent/DK1176956T3/da active
- 2000-05-05 MX MXPA01011340A patent/MXPA01011340A/es active IP Right Grant
- 2000-05-05 PL PL351396A patent/PL205322B1/pl unknown
- 2000-05-05 SI SI200020021A patent/SI20744B/sl not_active IP Right Cessation
- 2000-05-05 SK SK1608-2001A patent/SK286696B6/sk not_active IP Right Cessation
- 2000-05-05 JP JP2000616772A patent/JP5132855B2/ja not_active Expired - Fee Related
- 2000-05-05 WO PCT/US2000/012303 patent/WO2000067746A1/fr not_active Ceased
- 2000-05-05 CZ CZ20013963A patent/CZ303312B6/cs not_active IP Right Cessation
- 2000-05-05 CA CA2373360A patent/CA2373360C/fr not_active Expired - Lifetime
- 2000-05-05 AT AT00937527T patent/ATE383153T1/de active
- 2000-05-05 ES ES00937527T patent/ES2296625T3/es not_active Expired - Lifetime
- 2000-05-05 TR TR2002/01920T patent/TR200201920T2/xx unknown
- 2000-05-05 RO ROA200101210A patent/RO122246B1/ro unknown
- 2000-05-05 RU RU2001133360/04A patent/RU2263109C2/ru not_active IP Right Cessation
- 2000-05-05 EP EP00937527A patent/EP1176956B1/fr not_active Expired - Lifetime
- 2000-05-05 TR TR2001/03178T patent/TR200103178T2/xx unknown
- 2000-11-16 IN IN1110KON2001 patent/IN2001KN01110A/en unknown
2001
- 2001-10-24 ZA ZA200108774A patent/ZA200108774B/en unknown
- 2001-11-01 IL IL146311A patent/IL146311A/en not_active IP Right Cessation
- 2001-11-06 NO NO20015418A patent/NO324421B1/no not_active IP Right Cessation
2008
- 2008-03-05 CY CY20081100253T patent/CY1107438T1/el unknown

Also Published As

Publication number	Publication date
JP2002544161A (ja)	2002-12-24
CY1107438T1 (el)	2012-12-19
RU2263109C2 (ru)	2005-10-27
IN2001KN01110A (fr)	2015-06-05
AU5267900A (en)	2000-11-21
SI20744B (sl)	2009-08-31
WO2000067746A8 (fr)	2002-02-28
PL351396A1 (en)	2003-04-07
CA2373360A1 (fr)	2000-11-16
WO2000067746A1 (fr)	2000-11-16
HK1045805A1 (en)	2002-12-13
SI20744A (sl)	2002-06-30
ZA200108774B (en)	2003-01-24
NO20015418D0 (no)	2001-11-06
JP5132855B2 (ja)	2013-01-30
ES2296625T3 (es)	2008-05-01
IL146311A (en)	2011-10-31
EP1176956A4 (fr)	2002-08-28
IL146311A0 (en)	2002-07-25
ATE383153T1 (de)	2008-01-15
DK1176956T3 (da)	2008-05-26
WO2000067746A9 (fr)	2002-08-29
CZ20013963A3 (cs)	2002-04-17
CA2373360C (fr)	2011-09-06
EP1176956B1 (fr)	2008-01-09
NZ515248A (en)	2004-01-30
TR200103178T2 (tr)	2002-05-21
DE60037726D1 (de)	2008-02-21
SK16082001A3 (sk)	2002-04-04
EP1176956A1 (fr)	2002-02-06
CZ303312B6 (cs)	2012-07-25
DE60037726T2 (de)	2009-03-05
NO20015418L (no)	2001-12-21
TR200201920T2 (tr)	2002-09-23
PL205322B1 (pl)	2010-04-30
RO122246B1 (ro)	2009-03-30
NO324421B1 (no)	2007-10-08
MXPA01011340A (es)	2003-08-01

Publication	Publication Date	Title
SK286696B6 (sk)	2009-03-05	Deriváty karboxylovej kyseliny ako inhibítory väzby integrínov na svoje receptory, farmaceutická kompozícia obsahujúca ich a ich použitie
US6262084B1 (en)	2001-07-17	Compounds that inhibit the binding of integrins to their receptors
KR100767199B1 (ko)	2007-10-17	인테그린이 이의 수용체에 결합하는 것을 억제하는프로판산 유도체
US20030199692A1 (en)	2003-10-23	Propanoic acid derivatives that inhibit the binding of integrins to their receptors
SI21096A1 (sl)	2003-06-30	Derivati karboksilne kisline, ki inhibirajo vezavo integrinov na njihove receptorje
AU784156B2 (en)	2006-02-09	Propanoic acid derivatives that inhibit the binding of integrins to their receptors
AU759154B2 (en)	2003-04-10	Compounds that inhibit the binding of integrins to their receptors
KR100853950B1 (ko)	2008-08-25	인테그린이 이의 수용체에 결합하는 것을 억제하는카복실산 유도체
HK1045805B (en)	2008-12-24	Carboxylic acid derivatives that inhibit the binding of integrins to their receptors
SI21098A1 (sl)	2003-06-30	Derivati propanojske kisline, ki inhibirajo vezavo integrinov na njihove receptorje
ZA200108771B (en)	2003-01-24	Propanoic acid derivatives that inhibit the binding of integrins to their receptors.

Legal Events

Date	Code	Title	Description
2013-12-02	TC4A	Change of owner's name	Owner name: ENCYSIVE PHARMACEUTICALS, INC., NEW YORK, NEW , US Effective date: 20131007
2017-02-02	MM4A	Patent lapsed due to non-payment of maintenance fees	Effective date: 20160505

Date

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Title

Description

2013-12-02

TC4A

Change of owner's name

Owner name: ENCYSIVE PHARMACEUTICALS, INC., NEW YORK, NEW , US

Effective date: 20131007

2017-02-02

MM4A

Patent lapsed due to non-payment of maintenance fees

Effective date: 20160505