ES2292820T3 - 2-(3-sulfonilamino-2-oxopyrrolidin-1-yl)propanamidas como inhibidores del factor xa. - Google Patents
2-(3-sulfonilamino-2-oxopyrrolidin-1-yl)propanamidas como inhibidores del factor xa. Download PDFInfo
- Publication number
- ES2292820T3 ES2292820T3 ES02777533T ES02777533T ES2292820T3 ES 2292820 T3 ES2292820 T3 ES 2292820T3 ES 02777533 T ES02777533 T ES 02777533T ES 02777533 T ES02777533 T ES 02777533T ES 2292820 T3 ES2292820 T3 ES 2292820T3
- Authority
- ES
- Spain
- Prior art keywords
- amino
- oxopyrrolidin
- sulfonyl
- chloro
- naphthyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000003112 inhibitor Substances 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 176
- 238000000034 method Methods 0.000 claims abstract description 32
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- -1 (3S) -3 - {[(6-chloro-2-naphthyl) sulfonyl] amino} -2-oxopyrrolidin-1-yl Chemical group 0.000 claims description 457
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 118
- 125000000217 alkyl group Chemical group 0.000 claims description 86
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 83
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 80
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 75
- 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims description 62
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 38
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 23
- 239000012453 solvate Substances 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- BRRGSGRWNJJGEB-KKSFZXQISA-N (2s)-2-[(3s)-3-[(2-amino-2-oxoethyl)-(6-chloronaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]-n-[2-(carbamoylamino)ethyl]-n-propan-2-ylpropanamide Chemical compound O=C1N([C@@H](C)C(=O)N(CCNC(N)=O)C(C)C)CC[C@@H]1N(CC(N)=O)S(=O)(=O)C1=CC=C(C=C(Cl)C=C2)C2=C1 BRRGSGRWNJJGEB-KKSFZXQISA-N 0.000 claims description 17
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
- 125000005638 hydrazono group Chemical group 0.000 claims description 15
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- RIQHMAOZARRSCE-YWZLYKJASA-N (2s)-2-[(3s)-3-[(6-chloronaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]-n-(2-hydroxyethyl)-n-propan-2-ylpropanamide Chemical compound O=C1N([C@@H](C)C(=O)N(CCO)C(C)C)CC[C@@H]1NS(=O)(=O)C1=CC=C(C=C(Cl)C=C2)C2=C1 RIQHMAOZARRSCE-YWZLYKJASA-N 0.000 claims description 11
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 9
- URNLGUWXLQOSPP-LIRRHRJNSA-N (2s)-n-(2-amino-2-oxoethyl)-2-[(3s)-3-[(6-chloronaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]-n-propan-2-ylpropanamide Chemical compound O=C1N([C@@H](C)C(=O)N(CC(N)=O)C(C)C)CC[C@@H]1NS(=O)(=O)C1=CC=C(C=C(Cl)C=C2)C2=C1 URNLGUWXLQOSPP-LIRRHRJNSA-N 0.000 claims description 7
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 238000002560 therapeutic procedure Methods 0.000 claims description 7
- JJDIFJWXXSMKGZ-UUOWRZLLSA-N (2s)-2-[(3s)-3-[(2-amino-2-oxoethyl)-(6-chloronaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]-n-(2-cyanoethyl)-n-cyclopentylpropanamide Chemical compound O=C([C@@H](N1C([C@@H](N(CC(N)=O)S(=O)(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CC1)=O)C)N(CCC#N)C1CCCC1 JJDIFJWXXSMKGZ-UUOWRZLLSA-N 0.000 claims description 6
- QKGOEVVGKSORGS-AOMKIAJQSA-N (2s)-2-[(3s)-3-[(2-amino-2-oxoethyl)-(6-chloronaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]-n-(2-cyanoethyl)-n-cyclopropylpropanamide Chemical compound O=C([C@@H](N1C([C@@H](N(CC(N)=O)S(=O)(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CC1)=O)C)N(CCC#N)C1CC1 QKGOEVVGKSORGS-AOMKIAJQSA-N 0.000 claims description 6
- AQIQXBFMTBVKLX-KKSFZXQISA-N (2s)-2-[(3s)-3-[(2-amino-2-oxoethyl)-(6-chloronaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]-n-(2-hydroxyethyl)-n-propan-2-ylpropanamide Chemical compound O=C1N([C@@H](C)C(=O)N(CCO)C(C)C)CC[C@@H]1N(CC(N)=O)S(=O)(=O)C1=CC=C(C=C(Cl)C=C2)C2=C1 AQIQXBFMTBVKLX-KKSFZXQISA-N 0.000 claims description 6
- ORVNIRLLDIQNIF-SBUREZEXSA-N (2s)-2-[(3s)-3-[(6-chloronaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]-n-(2-cyanoethyl)-n-cyclopentylpropanamide Chemical compound O=C([C@@H](N1C([C@@H](NS(=O)(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CC1)=O)C)N(CCC#N)C1CCCC1 ORVNIRLLDIQNIF-SBUREZEXSA-N 0.000 claims description 6
- NNJMHYPCMMVMED-KKSFZXQISA-N (2s)-2-[(3s)-3-[(6-chloronaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]-n-(2-cyanoethyl)-n-propan-2-ylpropanamide Chemical compound O=C1N([C@@H](C)C(=O)N(CCC#N)C(C)C)CC[C@@H]1NS(=O)(=O)C1=CC=C(C=C(Cl)C=C2)C2=C1 NNJMHYPCMMVMED-KKSFZXQISA-N 0.000 claims description 6
- HLQIJPDUFSPOBV-YWZLYKJASA-N (2s)-2-[(3s)-3-[(6-chloronaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]-n-ethyl-n-propan-2-ylpropanamide Chemical compound O=C1N([C@@H](C)C(=O)N(C(C)C)CC)CC[C@@H]1NS(=O)(=O)C1=CC=C(C=C(Cl)C=C2)C2=C1 HLQIJPDUFSPOBV-YWZLYKJASA-N 0.000 claims description 6
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- PNZATZXFJZLWFP-AOMKIAJQSA-N (2s)-2-[(3s)-3-[(6-chloronaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]-n-(2-cyanoethyl)-n-cyclobutylpropanamide Chemical compound O=C([C@@H](N1C([C@@H](NS(=O)(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CC1)=O)C)N(CCC#N)C1CCC1 PNZATZXFJZLWFP-AOMKIAJQSA-N 0.000 claims description 5
- ABLGPKPAIZKHJR-ZOEDVAEJSA-N (2s)-n-(2-aminoethyl)-2-[(3s)-3-[(2-amino-2-oxoethyl)-(6-chloronaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]-n-propan-2-ylpropanamide;hydrochloride Chemical compound Cl.O=C1N([C@@H](C)C(=O)N(CCN)C(C)C)CC[C@@H]1N(CC(N)=O)S(=O)(=O)C1=CC=C(C=C(Cl)C=C2)C2=C1 ABLGPKPAIZKHJR-ZOEDVAEJSA-N 0.000 claims description 5
- NODFNDAAXRPXLM-ZOEDVAEJSA-N (2s)-n-(3-aminopropyl)-2-[(3s)-3-[(6-chloronaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]-n-propan-2-ylpropanamide;hydrochloride Chemical compound Cl.O=C1N([C@@H](C)C(=O)N(CCCN)C(C)C)CC[C@@H]1NS(=O)(=O)C1=CC=C(C=C(Cl)C=C2)C2=C1 NODFNDAAXRPXLM-ZOEDVAEJSA-N 0.000 claims description 5
- JZEAVKMYZLHYKS-DJWLMUNRSA-N 2-[(3S)-3-(2-amino-2-oxoethyl)-3-[[(E)-2-(5-chlorothiophen-2-yl)ethenyl]sulfonylamino]-2-oxopyrrolidin-1-yl]-N-ethyl-N-propan-2-ylpropanamide Chemical compound O=C1N(C(C)C(=O)N(C(C)C)CC)CC[C@@]1(CC(N)=O)NS(=O)(=O)\C=C\C1=CC=C(Cl)S1 JZEAVKMYZLHYKS-DJWLMUNRSA-N 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- CPYLFALFYKCLRI-UHFFFAOYSA-N 2-chloro-1-benzothiophene Chemical compound C1=CC=C2SC(Cl)=CC2=C1 CPYLFALFYKCLRI-UHFFFAOYSA-N 0.000 claims description 2
- JCTJUGQJEUUBES-UHFFFAOYSA-N 3-chloro-2-ethenylthiophene Chemical compound ClC=1C=CSC=1C=C JCTJUGQJEUUBES-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000006849 chlorophenylene group Chemical group 0.000 claims description 2
- 238000011161 development Methods 0.000 claims description 2
- 229940123583 Factor Xa inhibitor Drugs 0.000 abstract description 14
- 238000001819 mass spectrum Methods 0.000 description 177
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 86
- 239000000203 mixture Substances 0.000 description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
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- 230000002829 reductive effect Effects 0.000 description 37
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
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- 238000006243 chemical reaction Methods 0.000 description 17
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Classifications
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
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- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms 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
Landscapes
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Urology & Nephrology (AREA)
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- Psychiatry (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0127568.4A GB0127568D0 (en) | 2001-11-16 | 2001-11-16 | Chemical compounds |
| GB0127568 | 2001-11-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2292820T3 true ES2292820T3 (es) | 2008-03-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| ES02777533T Expired - Lifetime ES2292820T3 (es) | 2001-11-16 | 2002-11-13 | 2-(3-sulfonilamino-2-oxopyrrolidin-1-yl)propanamidas como inhibidores del factor xa. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7179835B2 (enExample) |
| EP (1) | EP1444201B1 (enExample) |
| JP (1) | JP2005521641A (enExample) |
| AT (1) | ATE372982T1 (enExample) |
| AU (1) | AU2002339158A1 (enExample) |
| DE (1) | DE60222459T2 (enExample) |
| ES (1) | ES2292820T3 (enExample) |
| GB (1) | GB0127568D0 (enExample) |
| WO (1) | WO2003043981A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0228552D0 (en) * | 2002-12-06 | 2003-01-15 | Glaxo Group Ltd | Chemical compounds |
| GB0228533D0 (en) * | 2002-12-06 | 2003-01-15 | Glaxo Group Ltd | Crystalline form |
| GB0314370D0 (en) * | 2003-06-19 | 2003-07-23 | Glaxo Group Ltd | Chemical compounds |
| TW200524858A (en) | 2003-06-19 | 2005-08-01 | Glaxo Group Ltd | Chemical compounds |
| GB0314299D0 (en) | 2003-06-19 | 2003-07-23 | Glaxo Group Ltd | Chemical compounds |
| GB0314373D0 (en) | 2003-06-19 | 2003-07-23 | Glaxo Group Ltd | Chemical compounds |
| WO2013057944A1 (ja) | 2011-10-19 | 2013-04-25 | 興和株式会社 | 新規なスピロインドリン化合物、及びそれを含有する医薬 |
| SI2989095T1 (sl) * | 2013-04-26 | 2019-03-29 | Sanofi | Tartratna sol 5-kloro-tiopen-2-karboksilne kisline((s)-2-(metil-3-(2-okso-pirolidin-1-il)-benzensulfonilamino)-3- (4-metil piperazin-1 il)-3-okso-propril)amida |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL92011A0 (en) | 1988-10-19 | 1990-07-12 | Abbott Lab | Heterocyclic peptide renin inhibitors |
| DE4121947A1 (de) | 1991-07-03 | 1993-01-07 | Basf Ag | 2-(3-(4-amidino-phenyl))-propionsaeurederivate, ihre herstellung und verwendung |
| US5703208A (en) * | 1994-06-17 | 1997-12-30 | Corvas International, Inc. | 3-amino-2-oxo-1-piperidineacetic derivatives as enzyme inhibitors |
| US5932733A (en) | 1994-06-17 | 1999-08-03 | Corvas International, Inc. | 3-amino-2-oxo-1-piperidineacetic derivatives containing an arginine mimic as enzyme inhibitors |
| WO1995035311A1 (en) | 1994-06-17 | 1995-12-28 | Corvas International, Inc. | 3-amino-2-oxo-1-piperidineacetic derivatives as enzyme inhibitors |
| US5719296A (en) * | 1995-10-30 | 1998-02-17 | Merck & Co., Inc. | Pseudopeptide lactam inhibitors of peptide binding to MHC class II proteins |
| WO1997016425A1 (en) | 1995-10-30 | 1997-05-09 | Merck & Co., Inc. | Novel inhibitors of peptide binding to mhc class ii proteins |
| CA2268281A1 (en) * | 1996-10-11 | 1998-04-23 | Cor Therapeutics, Inc. | Selective factor xa inhibitors |
| US6281227B1 (en) | 1996-12-13 | 2001-08-28 | Aventis Pharma Deutschland Gmbh | Sulfonic acid sulfonylamino n-(heteroaralkyl)-azaheterocyclylamide compounds |
| US6602864B1 (en) | 1996-12-13 | 2003-08-05 | Aventis Pharma Deutschland Gmbh | Sulfonic acid or sulfonylamino N-(heteroaralkyl)-azaheterocyclylamide compounds |
| EP0944386B1 (en) | 1996-12-13 | 2002-09-18 | Aventis Pharmaceuticals Inc. | Sulfonic acid or sulfonylamino n-(heteroaralkyl)-azaheterocyclylamide compounds |
| US6187797B1 (en) * | 1996-12-23 | 2001-02-13 | Dupont Pharmaceuticals Company | Phenyl-isoxazoles as factor XA Inhibitors |
| IL135180A0 (en) | 1997-09-30 | 2001-05-20 | Daiichi Seiyaku Co | Sulfonyl derivatives |
| ZA988967B (en) | 1997-10-03 | 2000-04-03 | Du Pont Pharm Co | Lactam metalloprotease inhibitors. |
| AU756174B2 (en) | 1999-02-09 | 2003-01-09 | Bristol-Myers Squibb Company | Lactam inhibitors of FXa and method |
| CA2376961A1 (en) | 1999-07-26 | 2001-02-01 | Bristol-Myers Squibb Pharma Company | Lactam inhibitors of hepatitis c virus ns3 protease |
| WO2001019795A1 (en) * | 1999-09-13 | 2001-03-22 | 3-Dimensional Pharmaceuticals, Inc. | Azacycloalkanone serine protease inhibitors |
| AU2001255408A1 (en) | 2000-04-14 | 2001-10-30 | Corvas International, Inc. | Tetrahydro-azepinone derivatives as thrombin inhibitors |
-
2001
- 2001-11-16 GB GBGB0127568.4A patent/GB0127568D0/en not_active Ceased
-
2002
- 2002-11-13 ES ES02777533T patent/ES2292820T3/es not_active Expired - Lifetime
- 2002-11-13 AU AU2002339158A patent/AU2002339158A1/en not_active Abandoned
- 2002-11-13 AT AT02777533T patent/ATE372982T1/de not_active IP Right Cessation
- 2002-11-13 WO PCT/GB2002/005134 patent/WO2003043981A1/en not_active Ceased
- 2002-11-13 US US10/495,586 patent/US7179835B2/en not_active Expired - Fee Related
- 2002-11-13 EP EP02777533A patent/EP1444201B1/en not_active Expired - Lifetime
- 2002-11-13 DE DE60222459T patent/DE60222459T2/de not_active Expired - Fee Related
- 2002-11-13 JP JP2003545618A patent/JP2005521641A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP1444201B1 (en) | 2007-09-12 |
| ATE372982T1 (de) | 2007-09-15 |
| GB0127568D0 (en) | 2002-01-09 |
| AU2002339158A1 (en) | 2003-06-10 |
| JP2005521641A (ja) | 2005-07-21 |
| US7179835B2 (en) | 2007-02-20 |
| EP1444201A1 (en) | 2004-08-11 |
| DE60222459T2 (de) | 2008-06-12 |
| WO2003043981A1 (en) | 2003-05-30 |
| DE60222459D1 (en) | 2007-10-25 |
| US20050004119A1 (en) | 2005-01-06 |
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